#------------------------------------------------------------------------------
#$Date: 2019-11-17 09:17:36 +0200 (Sun, 17 Nov 2019) $
#$Revision: 229058 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/23/01/7230138.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_7230138
loop_
_publ_author_name
'Pisk, Jana'
'Hrenar, Tomica'
'Rub\<ci\'c, Mirta'
'Pavlovi\'c, Gordana'
'Damjanovi\'c, Vladimir'
'Lovri\'c, Jasna'
'Cindri\'c, Marina'
'Vrdoljak, Vi\<snja'
_publ_section_title
;
 Comparative studies on conventional and solvent-free synthesis toward
 hydrazones: application of PXRD and chemometric data analysis in
 mechanochemical reaction monitoring
;
_journal_issue                   13
_journal_name_full               CrystEngComm
_journal_page_first              1804
_journal_paper_doi               10.1039/C7CE02136D
_journal_volume                  20
_journal_year                    2018
_chemical_formula_moiety         'C15 H15 N3 O3, C H4 O'
_chemical_formula_sum            'C16 H19 N3 O4'
_chemical_formula_weight         317.34
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2017-11-29 deposited with the CCDC.
2018-02-12 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 113.799(16)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   18.819(2)
_cell_length_b                   12.3035(8)
_cell_length_c                   15.245(2)
_cell_measurement_reflns_used    6784
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      31.1840
_cell_measurement_theta_min      4.4370
_cell_volume                     3229.7(7)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_molecular_graphics    'MERCURY 3.8. (CCDC, 2016)'
_computing_publication_material  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXT-2014/7 (Sheldrick, 2014)'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Xcalibur, Sapphire3'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0458
_diffrn_reflns_av_unetI/netI     0.0454
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            31536
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.500
_diffrn_reflns_theta_min         4.257
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.095
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.97841
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35.
Empirical absorption correction using 
spherical harmonics,
 implemented in SCALE3 ABSPACK 
scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.305
_exptl_crystal_description       prism
_exptl_crystal_F_000             1344
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.223
_refine_diff_density_min         -0.197
_refine_diff_density_rms         0.040
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     449
_refine_ls_number_reflns         7385
_refine_ls_number_restraints     10
_refine_ls_restrained_S_all      1.024
_refine_ls_R_factor_all          0.0790
_refine_ls_R_factor_gt           0.0488
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0384P)^2^+0.4272P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0930
_refine_ls_wR_factor_ref         0.1034
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5199
_reflns_number_total             7385
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c7ce02136d2.cif
_cod_data_source_block           4bMeOHexp1965
_cod_depositor_comments
'Adding full bibliography for 7230137--7230144.cif.'
_cod_original_cell_volume        3229.6(7)
_cod_database_code               7230138
_shelx_shelxl_version_number     2014/7
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_res_file
;

    shelx.res created by SHELXL-2014/7


TITL exp_1965 in P2(1)/c
CELL  0.71073  18.8190  12.3035  15.2447   90.000  113.799   90.000
ZERR     8.00   0.0022   0.0008   0.0022    0.000    0.016    0.000
LATT   1
SYMM  - X, 1/2 + Y, 1/2 - Z
SFAC  C    H    N    O
UNIT  128 152 24 32
MERG   2
OMIT    -1.00  55.00
dfix 0.84 o12 h12o o1me h1 o2me h2  o22 h22
dfix 0.88 n21 h21n n13 h13a n13 h13b n23 h23b n23 h23a  n11 h11n
FMAP   2
PLAN  100
ACTA
BOND   $H
HTAB O12 N12
HTAB O12 N11
HTAB O12 O11
EQIV $1 -x, y+1/2, -z-1/2
HTAB C1ME N23_$1
EQIV $2 -x+1, y-1/2, -z+1/2
HTAB C14 O12_$2
EQIV $3 x, y-1, z
HTAB C18 O1ME_$3
HTAB C24 O22_$1
HTAB C28 O2ME
EQIV $4 x, -y+1/2, z+1/2
HTAB C115 O22_$4
HTAB C115 O23_$4
EQIV $5 -x, -y+1, -z
HTAB C115 N23_$5
HTAB C115 N12_$4
EQIV $6 -x+1, y+1/2, -z+1/2
HTAB C212 N13_$6
HTAB C215 O12
HTAB C215 N21_$4
HTAB O1ME O11_$6
HTAB O2ME O21_$1
HTAB N11 O1ME_$3
HTAB N13 O12_$2
HTAB N13 O13_$2
EQIV $7 -x+1, -y+1, -z
HTAB N13 O1ME_$7
HTAB N21 O2ME
HTAB O22 N21
HTAB O22 N22
HTAB O22 O21
EQIV $8 -x, -y+1, -z-1
HTAB N23 O2ME_$8
HTAB N23 O22_$1
HTAB N23 O23_$1
CONF
L.S.  10
mpla 6  c12 c13 c14 c15 c16 c17
mpla 6 c19 c110 c111 c112 c113 c114

TEMP  -123.00
WGHT    0.038400    0.427200
FVAR       2.65864
N12   3    0.435810    0.091221    0.367016    11.00000    0.02750    0.03369 =
         0.02635   -0.00250    0.01349   -0.00207
N11   3    0.462162    0.063573    0.297866    11.00000    0.03318    0.02867 =
         0.02943   -0.00621    0.01811   -0.00474
N13   3    0.626921   -0.000362    0.007981    11.00000    0.03429    0.03917 =
         0.02891   -0.00006    0.01666    0.00368
N21   3    0.027849    0.475596   -0.165337    11.00000    0.03267    0.02929 =
         0.02208    0.00133    0.01052   -0.00266
N22   3    0.055950    0.448328   -0.070100    11.00000    0.02647    0.03240 =
         0.02314    0.00049    0.01001   -0.00001
N23   3   -0.125539    0.514423   -0.622429    11.00000    0.03646    0.04230 =
         0.02663    0.00199    0.01345    0.00285
O1ME  4    0.384772    0.881803    0.180507    11.00000    0.03145    0.02845 =
         0.04556   -0.00047    0.01587   -0.00052
O2ME  4    0.109879    0.637415   -0.220611    11.00000    0.03206    0.03025 =
         0.03745    0.00438    0.00920    0.00178
O11   4    0.505103    0.235699    0.298261    11.00000    0.04548    0.02737 =
         0.04569   -0.00861    0.02846   -0.00562
O12   4    0.392052    0.234145    0.459302    11.00000    0.04206    0.02873 =
         0.03648   -0.00146    0.02490   -0.00637
H12O  2    0.411555    0.209288    0.421433    11.00000   -1.20000
O13   4    0.327595    0.279641    0.576464    11.00000    0.04519    0.02955 =
         0.04319   -0.00507    0.02840   -0.00240
O21   4   -0.017025    0.303248   -0.201477    11.00000    0.04142    0.02938 =
         0.03050    0.00343    0.01126   -0.00489
O22   4    0.077910    0.302803    0.059228    11.00000    0.04172    0.03308 =
         0.02439    0.00053    0.00672   -0.01002
O23   4    0.145648    0.243497    0.236637    11.00000    0.04099    0.04351 =
         0.02771    0.00896    0.00688   -0.00509
C1ME  1    0.309978    0.837955    0.160614    11.00000    0.03595    0.04999 =
         0.07883   -0.00187    0.02466   -0.00552
AFIX 137
H1ME  2    0.314219    0.781026    0.207432    11.00000   -1.50000
H2ME  2    0.288518    0.806873    0.095927    11.00000   -1.50000
H3ME  2    0.275620    0.895730    0.164767    11.00000   -1.50000
AFIX   0
C2ME  1    0.186757    0.668806   -0.160781    11.00000    0.03424    0.05835 =
         0.05216    0.00451    0.00922   -0.00192
AFIX 137
H4ME  2    0.212579    0.697555   -0.200297    11.00000   -1.50000
H5ME  2    0.215484    0.605547   -0.124720    11.00000   -1.50000
H6ME  2    0.185359    0.725020   -0.115961    11.00000   -1.50000
AFIX   0
C11   1    0.498734    0.141466    0.267237    11.00000    0.02603    0.02808 =
         0.02651   -0.00062    0.01020   -0.00049
C12   1    0.530630    0.103665    0.199000    11.00000    0.02362    0.02643 =
         0.02407   -0.00293    0.00901   -0.00124
C13   1    0.551725   -0.005237    0.195900    11.00000    0.02515    0.02617 =
         0.02438    0.00037    0.00881   -0.00248
AFIX  43
H13   2    0.543760   -0.056702    0.237509    11.00000   -1.20000
AFIX   0
C14   1    0.583769   -0.038864    0.133629    11.00000    0.02632    0.02570 =
         0.02691   -0.00093    0.00944    0.00108
AFIX  43
H14   2    0.598947   -0.112612    0.134340    11.00000   -1.20000
AFIX   0
C15   1    0.594332    0.034043    0.069227    11.00000    0.02077    0.03351 =
         0.02201   -0.00343    0.00640   -0.00173
C16   1    0.572705    0.143347    0.071682    11.00000    0.03260    0.03114 =
         0.02604    0.00221    0.01345   -0.00289
AFIX  43
H16   2    0.579118    0.194520    0.028777    11.00000   -1.20000
AFIX   0
C17   1    0.542262    0.176690    0.135955    11.00000    0.03186    0.02451 =
         0.03134   -0.00158    0.01247   -0.00112
AFIX  43
H17   2    0.528950    0.250974    0.137264    11.00000   -1.20000
AFIX   0
C18   1    0.409254    0.014285    0.402998    11.00000    0.02700    0.02804 =
         0.03028   -0.00111    0.01174   -0.00001
AFIX  43
H18   2    0.410256   -0.058829    0.383491    11.00000   -1.20000
AFIX   0
C19   1    0.377766    0.039863    0.473550    11.00000    0.02164    0.02802 =
         0.02388    0.00056    0.00755   -0.00026
C21   1   -0.010469    0.395648   -0.229847    11.00000    0.02583    0.02856 =
         0.02866   -0.00108    0.01244    0.00057
C22   1   -0.041152    0.428454   -0.331456    11.00000    0.02305    0.03017 =
         0.02626    0.00034    0.01131   -0.00048
C23   1   -0.058859    0.536599   -0.360975    11.00000    0.02591    0.02891 =
         0.02741   -0.00260    0.01136    0.00023
AFIX  43
H23   2   -0.051330    0.591597   -0.314319    11.00000   -1.20000
AFIX   0
C24   1   -0.086973    0.564474   -0.456416    11.00000    0.02788    0.03096 =
         0.02991    0.00385    0.01195    0.00492
AFIX  43
H24   2   -0.099707    0.638101   -0.474825    11.00000   -1.20000
AFIX   0
C25   1   -0.097048    0.485768   -0.526708    11.00000    0.02186    0.03900 =
         0.02457    0.00129    0.01014   -0.00028
C26   1   -0.079347    0.377116   -0.497624    11.00000    0.03465    0.03234 =
         0.02707   -0.00639    0.01360   -0.00316
AFIX  43
H26   2   -0.086232    0.322258   -0.544213    11.00000   -1.20000
AFIX   0
C27   1   -0.052022    0.349540   -0.401826    11.00000    0.03173    0.02718 =
         0.03188    0.00047    0.01415   -0.00148
AFIX  43
H27   2   -0.040399    0.275711   -0.383362    11.00000   -1.20000
AFIX   0
C28   1    0.094165    0.518868   -0.006749    11.00000    0.02792    0.02706 =
         0.02963    0.00074    0.01333    0.00146
AFIX  43
H28   2    0.100737    0.590607   -0.025295    11.00000   -1.20000
AFIX   0
C29   1    0.127376    0.487806    0.093927    11.00000    0.02160    0.03156 =
         0.02582   -0.00251    0.01120    0.00167
C110  1    0.369502    0.147659    0.497091    11.00000    0.02242    0.02872 =
         0.02240    0.00225    0.00758   -0.00401
C111  1    0.334070    0.170922    0.560952    11.00000    0.02336    0.02973 =
         0.02521   -0.00202    0.00833   -0.00189
C112  1    0.308553    0.086402    0.600630    11.00000    0.02636    0.03814 =
         0.02630    0.00189    0.01339   -0.00005
AFIX  43
H112  2    0.284226    0.101546    0.643092    11.00000   -1.20000
AFIX   0
C113  1    0.318448   -0.021321    0.578438    11.00000    0.03139    0.03211 =
         0.03278    0.00716    0.01467   -0.00221
AFIX  43
H113  2    0.301377   -0.078888    0.606717    11.00000   -1.20000
AFIX   0
C114  1    0.352487   -0.044767    0.516370    11.00000    0.03076    0.02602 =
         0.03177    0.00223    0.01198   -0.00027
AFIX  43
H114  2    0.359070   -0.118300    0.502152    11.00000   -1.20000
AFIX   0
C115  1    0.288455    0.308235    0.636354    11.00000    0.04907    0.04171 =
         0.05023   -0.01059    0.03265   -0.00135
AFIX 137
H15A  2    0.236000    0.277334    0.609785    11.00000   -1.50000
H15B  2    0.285155    0.387546    0.639332    11.00000   -1.50000
H15C  2    0.317374    0.279431    0.701011    11.00000   -1.50000
AFIX   0
C210  1    0.119453    0.381383    0.121824    11.00000    0.02186    0.03302 =
         0.02483   -0.00388    0.01022   -0.00193
C211  1    0.157209    0.350326    0.218569    11.00000    0.02557    0.03829 =
         0.02780    0.00126    0.01270   -0.00077
C212  1    0.202097    0.425069    0.285922    11.00000    0.02606    0.04803 =
         0.02341   -0.00297    0.00802    0.00400
AFIX  43
H212  2    0.228546    0.403803    0.351024    11.00000   -1.20000
AFIX   0
C213  1    0.208684    0.531512    0.258653    11.00000    0.02968    0.04195 =
         0.03023   -0.01054    0.00958    0.00021
AFIX  43
H213  2    0.239190    0.582518    0.305498    11.00000   -1.20000
AFIX   0
C214  1    0.171339    0.563331    0.164377    11.00000    0.02827    0.03045 =
         0.03440   -0.00624    0.01214    0.00026
AFIX  43
H214  2    0.175246    0.636459    0.146813    11.00000   -1.20000
AFIX   0
C215  1    0.185564    0.205700    0.332810    11.00000    0.04704    0.05636 =
         0.03342    0.01563    0.00933    0.00420
AFIX 137
H25A  2    0.241347    0.219272    0.354066    11.00000   -1.50000
H25B  2    0.176569    0.127543    0.335434    11.00000   -1.50000
H25C  2    0.166156    0.244358    0.374896    11.00000   -1.50000
AFIX   0
H1    2    0.416651    0.828542    0.188387    11.00000   -1.20000
H2    2    0.082904    0.695589   -0.243075    11.00000   -1.20000
H11N  2    0.446349    0.001093    0.266653    11.00000   -1.20000
H13A  2    0.628086   -0.072115   -0.000263    11.00000   -1.20000
H13B  2    0.619766    0.041502   -0.042484    11.00000   -1.20000
H21N  2    0.046063    0.534457   -0.183996    11.00000   -1.20000
H22   2    0.061840    0.335658    0.004193    11.00000   -1.20000
H23B  2   -0.115060    0.467747   -0.660422    11.00000   -1.20000
H23A  2   -0.119972    0.584443   -0.633842    11.00000   -1.20000
HKLF    4

REM  exp_1965 in P2(1)/c
REM R1 =  0.0488 for    5199 Fo > 4sig(Fo)  and  0.0790 for all    7385 data
REM    449 parameters refined using     10 restraints

END

WGHT      0.0386      0.4303

REM Highest difference peak  0.223,  deepest hole -0.197,  1-sigma level  0.040
Q1    1   0.3483  0.0956  0.4575  11.00000  0.05    0.22
Q2    1  -0.0713  0.4670 -0.3421  11.00000  0.05    0.22
Q3    1   0.1523  0.4312  0.1055  11.00000  0.05    0.20
Q4    1   0.5613  0.0578  0.2200  11.00000  0.05    0.19
Q5    1   0.1604  0.3632  0.1710  11.00000  0.05    0.17
Q6    1  -0.0579  0.3849 -0.3583  11.00000  0.05    0.17
Q7    1   0.1620  0.5166  0.1191  11.00000  0.05    0.17
Q8    1   0.3985  0.0904  0.5125  11.00000  0.05    0.17
Q9    1   0.1041  0.4426  0.1084  11.00000  0.05    0.17
Q10   1  -0.0237  0.4186 -0.2871  11.00000  0.05    0.17
Q11   1   0.1974  0.3760  0.2402  11.00000  0.05    0.16
Q12   1   0.3891  0.0002  0.5094  11.00000  0.05    0.15
Q13   1   0.0385  0.7430 -0.2472  11.00000  0.05    0.15
Q14   1   0.2188  0.6408 -0.0712  11.00000  0.05    0.15
Q15   1   0.6110  0.0139  0.1305  11.00000  0.05    0.15
Q16   1   0.0904  0.5750 -0.1931  11.00000  0.05    0.15
Q17   1  -0.0438  0.5485 -0.4048  11.00000  0.05    0.14
Q18   1   0.3370  0.1536  0.5169  11.00000  0.05    0.14
Q19   1   0.0176  0.3934 -0.0757  11.00000  0.05    0.14
Q20   1   0.2401  0.1621  0.3423  11.00000  0.05    0.14
Q21   1   0.2280  0.6035 -0.1855  11.00000  0.05    0.14
Q22   1   0.5489  0.1803 -0.0004  11.00000  0.05    0.14
Q23   1   0.4017  0.1586  0.3554  11.00000  0.05    0.14
Q24   1   0.2885  0.1323  0.5539  11.00000  0.05    0.14
Q25   1   0.5785  0.1515  0.2027  11.00000  0.05    0.14
Q26   1   0.3777  0.0245  0.4365  11.00000  0.05    0.14
Q27   1  -0.0202  0.1591 -0.3411  11.00000  0.05    0.14
Q28   1   0.3474  0.0030  0.4758  11.00000  0.05    0.14
Q29   1  -0.0317  0.4814 -0.3402  11.00000  0.05    0.14
Q30   1   0.3733  0.1575  0.5507  11.00000  0.05    0.13
Q31   1   0.1000  0.0838  0.2349  11.00000  0.05    0.13
Q32   1   0.3194  0.8223  0.2418  11.00000  0.05    0.13
Q33   1   0.5188  0.1768  0.3419  11.00000  0.05    0.13
Q34   1   0.3316  0.0367  0.6049  11.00000  0.05    0.13
Q35   1   0.5791 -0.0011  0.0901  11.00000  0.05    0.13
Q36   1   0.2710  0.1841  0.3290  11.00000  0.05    0.13
Q37   1  -0.0739  0.5239 -0.4853  11.00000  0.05    0.13
Q38   1   0.5266  0.1177  0.2396  11.00000  0.05    0.13
Q39   1  -0.1962  0.4959 -0.6752  11.00000  0.05    0.13
Q40   1   0.1649  0.5574  0.2237  11.00000  0.05    0.13
Q41   1   0.2113  0.0263  0.5235  11.00000  0.05    0.13
Q42   1   0.4562  0.2398  0.5295  11.00000  0.05    0.13
Q43   1   0.2840  0.0274  0.5553  11.00000  0.05    0.13
Q44   1   0.5301  0.1365  0.1711  11.00000  0.05    0.13
Q45   1  -0.0077  0.4713 -0.0672  11.00000  0.05    0.13
Q46   1  -0.0822  0.4397 -0.5112  11.00000  0.05    0.12
Q47   1   0.5323 -0.0355  0.1289  11.00000  0.05    0.12
Q48   1   0.2824  0.2935  0.3580  11.00000  0.05    0.12
Q49   1   0.6770 -0.0433  0.0309  11.00000  0.05    0.12
Q50   1   0.4566  0.0470  0.4252  11.00000  0.05    0.12
Q51   1   0.3189  0.2370  0.3501  11.00000  0.05    0.12
Q52   1   0.2090  0.1801  0.5783  11.00000  0.05    0.12
Q53   1   0.3222  0.3934  0.6856  11.00000  0.05    0.12
Q54   1   0.4028  0.2770  0.5153  11.00000  0.05    0.12
Q55   1   0.2569  0.3514  0.3983  11.00000  0.05    0.12
Q56   1   0.4943  0.2341  0.3509  11.00000  0.05    0.12
Q57   1   0.4571 -0.1343  0.5556  11.00000  0.05    0.12
Q58   1  -0.1180  0.5222 -0.4986  11.00000  0.05    0.12
Q59   1   0.1077  0.5402 -0.2216  11.00000  0.05    0.12
Q60   1   0.5332 -0.0241 -0.0396  11.00000  0.05    0.12
Q61   1   0.5598 -0.0541 -0.0902  11.00000  0.05    0.12
Q62   1   0.0760  0.2398  0.1737  11.00000  0.05    0.12
Q63   1   0.0934  0.5126  0.0494  11.00000  0.05    0.12
Q64   1   0.1473  0.0948  0.3069  11.00000  0.05    0.12
Q65   1   0.1201  0.3856  0.1781  11.00000  0.05    0.12
Q66   1  -0.0301  0.3716 -0.4502  11.00000  0.05    0.12
Q67   1   0.4443  0.0167  0.5613  11.00000  0.05    0.12
Q68   1   0.1296  0.1981  0.1725  11.00000  0.05    0.12
Q69   1   0.4706  0.1377  0.4168  11.00000  0.05    0.12
Q70   1   0.4962  0.8397  0.2901  11.00000  0.05    0.12
Q71   1   0.5642  0.2187 -0.0693  11.00000  0.05    0.12
Q72   1  -0.1157  0.3387 -0.4656  11.00000  0.05    0.11
Q73   1   0.3828  0.2818  0.6571  11.00000  0.05    0.11
Q74   1   0.4035  0.7627  0.2481  11.00000  0.05    0.11
Q75   1   0.5276  0.0267  0.3713  11.00000  0.05    0.11
Q76   1   0.5386  0.2577  0.3323  11.00000  0.05    0.11
Q77   1   0.3970  0.0992  0.2265  11.00000  0.05    0.11
Q78   1   0.2739  0.1172  0.6779  11.00000  0.05    0.11
Q79   1  -0.0058  0.4392 -0.1951  11.00000  0.05    0.11
Q80   1   0.1915  0.5873 -0.0239  11.00000  0.05    0.11
Q81   1   0.0428  0.2797 -0.2946  11.00000  0.05    0.11
Q82   1   0.2030  0.1295  0.6189  11.00000  0.05    0.11
Q83   1   0.5028  0.2151 -0.0406  11.00000  0.05    0.11
Q84   1   0.0808  0.3794 -0.0399  11.00000  0.05    0.11
Q85   1  -0.0456  0.5840 -0.6617  11.00000  0.05    0.11
Q86   1  -0.0677  0.2999 -0.5964  11.00000  0.05    0.11
Q87   1  -0.0417  0.5420 -0.6222  11.00000  0.05    0.11
Q88   1   0.2077  0.4208  0.5691  11.00000  0.05    0.11
Q89   1   0.0368  0.4543  0.0969  11.00000  0.05    0.11
Q90   1   0.2154  0.7342 -0.1459  11.00000  0.05    0.11
Q91   1   0.3021  0.2218  0.5368  11.00000  0.05    0.11
Q92   1   0.1756  0.4949  0.2850  11.00000  0.05    0.11
Q93   1   0.6327  0.0587 -0.1061  11.00000  0.05    0.11
Q94   1   0.0094  0.5605 -0.3728  11.00000  0.05    0.11
Q95   1   0.0723  0.6157  0.1431  11.00000  0.05    0.11
Q96   1   0.2770  0.8871  0.1017  11.00000  0.05    0.11
Q97   1   0.0623  0.5847 -0.2673  11.00000  0.05    0.11
Q98   1   0.1308  0.5253  0.1371  11.00000  0.05    0.11
Q99   1   0.1297  0.4824  0.0420  11.00000  0.05    0.11
Q100  1   0.4023  0.9562  0.2102  11.00000  0.05    0.11
;
_shelx_res_checksum              56937
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
N12 N 0.43581(7) 0.09122(11) 0.36702(9) 0.0283(3) Uani 1 1 d . .
N11 N 0.46216(8) 0.06357(11) 0.29787(9) 0.0287(3) Uani 1 1 d D .
N13 N 0.62692(8) -0.00036(13) 0.00798(10) 0.0329(3) Uani 1 1 d D .
N21 N 0.02785(8) 0.47560(11) -0.16534(9) 0.0282(3) Uani 1 1 d D .
N22 N 0.05595(7) 0.44833(11) -0.07010(9) 0.0273(3) Uani 1 1 d . .
N23 N -0.12554(8) 0.51442(13) -0.62243(10) 0.0349(3) Uani 1 1 d D .
O1ME O 0.38477(7) 0.88180(9) 0.18051(8) 0.0350(3) Uani 1 1 d D .
O2ME O 0.10988(7) 0.63742(9) -0.22061(8) 0.0348(3) Uani 1 1 d D .
O11 O 0.50510(7) 0.23570(9) 0.29826(8) 0.0363(3) Uani 1 1 d . .
O12 O 0.39205(7) 0.23414(9) 0.45930(8) 0.0328(3) Uani 1 1 d D .
H12O H 0.4116(10) 0.2093(14) 0.4214(12) 0.039 Uiso 1 1 d D U
O13 O 0.32760(7) 0.27964(9) 0.57646(8) 0.0359(3) Uani 1 1 d . .
O21 O -0.01702(7) 0.30325(9) -0.20148(8) 0.0348(3) Uani 1 1 d . .
O22 O 0.07791(7) 0.30280(9) 0.05923(8) 0.0352(3) Uani 1 1 d D .
O23 O 0.14565(7) 0.24350(10) 0.23664(8) 0.0396(3) Uani 1 1 d . .
C1ME C 0.30998(11) 0.83796(17) 0.16061(16) 0.0544(6) Uani 1 1 d . .
H1ME H 0.3142 0.7810 0.2074 0.082 Uiso 1 1 calc R U
H2ME H 0.2885 0.8069 0.0959 0.082 Uiso 1 1 calc R U
H3ME H 0.2756 0.8957 0.1648 0.082 Uiso 1 1 calc R U
C2ME C 0.18676(11) 0.66881(17) -0.16078(14) 0.0509(5) Uani 1 1 d . .
H4ME H 0.2126 0.6976 -0.2003 0.076 Uiso 1 1 calc R U
H5ME H 0.2155 0.6055 -0.1247 0.076 Uiso 1 1 calc R U
H6ME H 0.1854 0.7250 -0.1160 0.076 Uiso 1 1 calc R U
C11 C 0.49873(9) 0.14147(13) 0.26724(11) 0.0270(4) Uani 1 1 d . .
C12 C 0.53063(9) 0.10366(12) 0.19900(10) 0.0249(3) Uani 1 1 d . .
C13 C 0.55173(8) -0.00524(13) 0.19590(10) 0.0256(3) Uani 1 1 d . .
H13 H 0.5438 -0.0567 0.2375 0.031 Uiso 1 1 calc R U
C14 C 0.58377(9) -0.03886(13) 0.13363(10) 0.0267(3) Uani 1 1 d . .
H14 H 0.5989 -0.1126 0.1343 0.032 Uiso 1 1 calc R U
C15 C 0.59433(8) 0.03404(13) 0.06923(10) 0.0261(3) Uani 1 1 d . .
C16 C 0.57271(9) 0.14335(13) 0.07168(11) 0.0294(4) Uani 1 1 d . .
H16 H 0.5791 0.1945 0.0288 0.035 Uiso 1 1 calc R U
C17 C 0.54226(9) 0.17669(13) 0.13595(11) 0.0293(4) Uani 1 1 d . .
H17 H 0.5290 0.2510 0.1373 0.035 Uiso 1 1 calc R U
C18 C 0.40925(9) 0.01428(13) 0.40300(11) 0.0284(4) Uani 1 1 d . .
H18 H 0.4103 -0.0588 0.3835 0.034 Uiso 1 1 calc R U
C19 C 0.37777(8) 0.03986(12) 0.47355(10) 0.0250(3) Uani 1 1 d . .
C21 C -0.01047(9) 0.39565(13) -0.22985(11) 0.0272(4) Uani 1 1 d . .
C22 C -0.04115(9) 0.42845(13) -0.33146(11) 0.0261(3) Uani 1 1 d . .
C23 C -0.05886(9) 0.53660(13) -0.36097(11) 0.0272(4) Uani 1 1 d . .
H23 H -0.0513 0.5916 -0.3143 0.033 Uiso 1 1 calc R U
C24 C -0.08697(9) 0.56447(14) -0.45642(11) 0.0295(4) Uani 1 1 d . .
H24 H -0.0997 0.6381 -0.4748 0.035 Uiso 1 1 calc R U
C25 C -0.09705(9) 0.48577(14) -0.52671(10) 0.0282(4) Uani 1 1 d . .
C26 C -0.07935(9) 0.37712(13) -0.49762(11) 0.0310(4) Uani 1 1 d . .
H26 H -0.0862 0.3223 -0.5442 0.037 Uiso 1 1 calc R U
C27 C -0.05202(9) 0.34954(14) -0.40183(11) 0.0298(4) Uani 1 1 d . .
H27 H -0.0404 0.2757 -0.3834 0.036 Uiso 1 1 calc R U
C28 C 0.09417(9) 0.51887(13) -0.00675(11) 0.0277(4) Uani 1 1 d . .
H28 H 0.1007 0.5906 -0.0253 0.033 Uiso 1 1 calc R U
C29 C 0.12738(8) 0.48781(13) 0.09393(10) 0.0258(3) Uani 1 1 d . .
C110 C 0.36950(9) 0.14766(13) 0.49709(10) 0.0250(3) Uani 1 1 d . .
C111 C 0.33407(9) 0.17092(13) 0.56095(11) 0.0266(3) Uani 1 1 d . .
C112 C 0.30855(9) 0.08640(14) 0.60063(11) 0.0294(4) Uani 1 1 d . .
H112 H 0.2842 0.1015 0.6431 0.035 Uiso 1 1 calc R U
C113 C 0.31845(9) -0.02132(14) 0.57844(11) 0.0315(4) Uani 1 1 d . .
H113 H 0.3014 -0.0789 0.6067 0.038 Uiso 1 1 calc R U
C114 C 0.35249(9) -0.04477(13) 0.51637(11) 0.0297(4) Uani 1 1 d . .
H114 H 0.3591 -0.1183 0.5022 0.036 Uiso 1 1 calc R U
C115 C 0.28846(11) 0.30823(15) 0.63635(14) 0.0429(5) Uani 1 1 d . .
H15A H 0.2360 0.2773 0.6098 0.064 Uiso 1 1 calc R U
H15B H 0.2852 0.3875 0.6393 0.064 Uiso 1 1 calc R U
H15C H 0.3174 0.2794 0.7010 0.064 Uiso 1 1 calc R U
C210 C 0.11945(9) 0.38138(13) 0.12182(10) 0.0263(3) Uani 1 1 d . .
C211 C 0.15721(9) 0.35033(14) 0.21857(11) 0.0299(4) Uani 1 1 d . .
C212 C 0.20210(9) 0.42507(15) 0.28592(11) 0.0331(4) Uani 1 1 d . .
H212 H 0.2285 0.4038 0.3510 0.040 Uiso 1 1 calc R U
C213 C 0.20868(10) 0.53151(15) 0.25865(12) 0.0348(4) Uani 1 1 d . .
H213 H 0.2392 0.5825 0.3055 0.042 Uiso 1 1 calc R U
C214 C 0.17134(9) 0.56333(14) 0.16438(11) 0.0312(4) Uani 1 1 d . .
H214 H 0.1752 0.6365 0.1468 0.037 Uiso 1 1 calc R U
C215 C 0.18556(11) 0.20570(17) 0.33281(12) 0.0478(5) Uani 1 1 d . .
H25A H 0.2413 0.2193 0.3541 0.072 Uiso 1 1 calc R U
H25B H 0.1766 0.1275 0.3354 0.072 Uiso 1 1 calc R U
H25C H 0.1662 0.2444 0.3749 0.072 Uiso 1 1 calc R U
H1 H 0.4167(11) 0.8285(14) 0.1884(14) 0.057 Uiso 1 1 d D U
H2 H 0.0829(11) 0.6956(14) -0.2431(14) 0.057 Uiso 1 1 d D U
H11N H 0.4463(11) 0.0011(13) 0.2667(13) 0.057 Uiso 1 1 d D U
H13A H 0.6281(12) -0.0721(12) -0.0003(14) 0.057 Uiso 1 1 d D U
H13B H 0.6198(12) 0.0415(15) -0.0425(12) 0.057 Uiso 1 1 d D U
H21N H 0.0461(11) 0.5345(13) -0.1840(13) 0.057 Uiso 1 1 d D U
H22 H 0.0618(11) 0.3357(15) 0.0042(11) 0.057 Uiso 1 1 d D U
H23B H -0.1151(11) 0.4677(14) -0.6604(13) 0.057 Uiso 1 1 d D U
H23A H -0.1200(12) 0.5844(13) -0.6338(14) 0.057 Uiso 1 1 d D U
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
N12 0.0275(7) 0.0337(8) 0.0264(7) -0.0025(6) 0.0135(6) -0.0021(6)
N11 0.0332(8) 0.0287(8) 0.0294(7) -0.0062(6) 0.0181(6) -0.0047(6)
N13 0.0343(8) 0.0392(9) 0.0289(8) -0.0001(7) 0.0167(6) 0.0037(7)
N21 0.0327(7) 0.0293(8) 0.0221(7) 0.0013(6) 0.0105(6) -0.0027(6)
N22 0.0265(7) 0.0324(8) 0.0231(7) 0.0005(6) 0.0100(6) 0.0000(6)
N23 0.0365(8) 0.0423(9) 0.0266(8) 0.0020(7) 0.0135(6) 0.0028(7)
O1ME 0.0315(7) 0.0285(7) 0.0456(7) -0.0005(5) 0.0159(6) -0.0005(5)
O2ME 0.0321(7) 0.0303(7) 0.0374(7) 0.0044(5) 0.0092(5) 0.0018(5)
O11 0.0455(7) 0.0274(7) 0.0457(7) -0.0086(5) 0.0285(6) -0.0056(5)
O12 0.0421(7) 0.0287(6) 0.0365(7) -0.0015(5) 0.0249(6) -0.0064(5)
O13 0.0452(7) 0.0295(7) 0.0432(7) -0.0051(5) 0.0284(6) -0.0024(5)
O21 0.0414(7) 0.0294(7) 0.0305(6) 0.0034(5) 0.0113(5) -0.0049(5)
O22 0.0417(7) 0.0331(7) 0.0244(6) 0.0005(5) 0.0067(5) -0.0100(5)
O23 0.0410(7) 0.0435(8) 0.0277(6) 0.0090(5) 0.0069(5) -0.0051(6)
C1ME 0.0359(11) 0.0500(13) 0.0788(15) -0.0019(11) 0.0247(11) -0.0055(9)
C2ME 0.0342(10) 0.0583(13) 0.0522(12) 0.0045(10) 0.0092(9) -0.0019(9)
C11 0.0260(8) 0.0281(9) 0.0265(8) -0.0006(7) 0.0102(7) -0.0005(7)
C12 0.0236(8) 0.0264(8) 0.0241(8) -0.0029(7) 0.0090(7) -0.0012(7)
C13 0.0252(8) 0.0262(9) 0.0244(8) 0.0004(7) 0.0088(6) -0.0025(7)
C14 0.0263(8) 0.0257(9) 0.0269(8) -0.0009(7) 0.0094(7) 0.0011(7)
C15 0.0208(7) 0.0335(9) 0.0220(8) -0.0034(7) 0.0064(6) -0.0017(7)
C16 0.0326(9) 0.0311(9) 0.0260(8) 0.0022(7) 0.0135(7) -0.0029(7)
C17 0.0319(9) 0.0245(9) 0.0313(9) -0.0016(7) 0.0125(7) -0.0011(7)
C18 0.0270(8) 0.0280(9) 0.0303(8) -0.0011(7) 0.0117(7) 0.0000(7)
C19 0.0216(8) 0.0280(9) 0.0239(8) 0.0006(7) 0.0076(6) -0.0003(6)
C21 0.0258(8) 0.0286(9) 0.0287(8) -0.0011(7) 0.0124(7) 0.0006(7)
C22 0.0230(8) 0.0302(9) 0.0263(8) 0.0003(7) 0.0113(7) -0.0005(7)
C23 0.0259(8) 0.0289(9) 0.0274(8) -0.0026(7) 0.0114(7) 0.0002(7)
C24 0.0279(8) 0.0310(9) 0.0299(9) 0.0038(7) 0.0119(7) 0.0049(7)
C25 0.0219(8) 0.0390(10) 0.0246(8) 0.0013(7) 0.0101(6) -0.0003(7)
C26 0.0347(9) 0.0323(9) 0.0271(8) -0.0064(7) 0.0136(7) -0.0032(7)
C27 0.0317(9) 0.0272(9) 0.0319(9) 0.0005(7) 0.0141(7) -0.0015(7)
C28 0.0279(8) 0.0271(9) 0.0296(8) 0.0007(7) 0.0133(7) 0.0015(7)
C29 0.0216(8) 0.0316(9) 0.0258(8) -0.0025(7) 0.0112(6) 0.0017(7)
C110 0.0224(8) 0.0287(9) 0.0224(8) 0.0023(7) 0.0076(6) -0.0040(7)
C111 0.0234(8) 0.0297(9) 0.0252(8) -0.0020(7) 0.0083(7) -0.0019(7)
C112 0.0264(8) 0.0381(10) 0.0263(8) 0.0019(7) 0.0134(7) -0.0001(7)
C113 0.0314(9) 0.0321(9) 0.0328(9) 0.0072(7) 0.0147(7) -0.0022(7)
C114 0.0308(9) 0.0260(9) 0.0318(9) 0.0022(7) 0.0120(7) -0.0003(7)
C115 0.0491(11) 0.0417(11) 0.0502(11) -0.0106(9) 0.0327(10) -0.0014(9)
C210 0.0219(8) 0.0330(9) 0.0248(8) -0.0039(7) 0.0102(7) -0.0019(7)
C211 0.0256(8) 0.0383(10) 0.0278(9) 0.0013(7) 0.0127(7) -0.0008(7)
C212 0.0261(8) 0.0480(11) 0.0234(8) -0.0030(8) 0.0080(7) 0.0040(8)
C213 0.0297(9) 0.0420(11) 0.0302(9) -0.0105(8) 0.0096(7) 0.0002(8)
C214 0.0283(9) 0.0304(9) 0.0344(9) -0.0062(7) 0.0121(7) 0.0003(7)
C215 0.0470(11) 0.0564(13) 0.0334(10) 0.0156(9) 0.0093(9) 0.0042(10)
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C18 N12 N11 117.70(13)
C11 N11 N12 118.35(13)
C11 N11 H11N 121.9(13)
N12 N11 H11N 118.5(13)
C15 N13 H13A 116.3(13)
C15 N13 H13B 117.1(13)
H13A N13 H13B 117.0(18)
N22 N21 C21 116.75(13)
N22 N21 H21N 120.1(12)
C21 N21 H21N 120.7(12)
C28 N22 N21 119.44(13)
C25 N23 H23B 115.3(13)
C25 N23 H23A 115.2(13)
H23B N23 H23A 114.8(18)
C1ME O1ME H1 108.3(14)
C2ME O2ME H2 108.2(14)
C110 O12 H12O 107.4(12)
C111 O13 C115 117.03(13)
C210 O22 H22 103.0(13)
C211 O23 C215 117.10(13)
O1ME C1ME H1ME 109.5
O1ME C1ME H2ME 109.5
H1ME C1ME H2ME 109.5
O1ME C1ME H3ME 109.5
H1ME C1ME H3ME 109.5
H2ME C1ME H3ME 109.5
O2ME C2ME H4ME 109.5
O2ME C2ME H5ME 109.5
H4ME C2ME H5ME 109.5
O2ME C2ME H6ME 109.5
H4ME C2ME H6ME 109.5
H5ME C2ME H6ME 109.5
O11 C11 N11 120.65(14)
O11 C11 C12 124.16(14)
N11 C11 C12 115.17(14)
C17 C12 C13 117.78(14)
C17 C12 C11 120.37(14)
C13 C12 C11 121.83(14)
C14 C13 C12 121.21(14)
C14 C13 H13 119.4
C12 C13 H13 119.4
C13 C14 C15 121.04(15)
C13 C14 H14 119.5
C15 C14 H14 119.5
N13 C15 C14 120.46(15)
N13 C15 C16 121.63(15)
C14 C15 C16 117.88(14)
C17 C16 C15 120.58(15)
C17 C16 H16 119.7
C15 C16 H16 119.7
C16 C17 C12 121.48(15)
C16 C17 H17 119.3
C12 C17 H17 119.3
N12 C18 C19 119.85(15)
N12 C18 H18 120.1
C19 C18 H18 120.1
C110 C19 C114 119.23(14)
C110 C19 C18 120.98(14)
C114 C19 C18 119.75(14)
O21 C21 N21 120.32(14)
O21 C21 C22 124.44(14)
N21 C21 C22 115.25(14)
C27 C22 C23 118.06(14)
C27 C22 C21 119.31(14)
C23 C22 C21 122.61(14)
C24 C23 C22 121.10(15)
C24 C23 H23 119.5
C22 C23 H23 119.5
C23 C24 C25 120.85(15)
C23 C24 H24 119.6
C25 C24 H24 119.6
N23 C25 C24 120.47(15)
N23 C25 C26 121.15(15)
C24 C25 C26 118.36(14)
C27 C26 C25 120.47(15)
C27 C26 H26 119.8
C25 C26 H26 119.8
C26 C27 C22 121.15(15)
C26 C27 H27 119.4
C22 C27 H27 119.4
N22 C28 C29 119.24(14)
N22 C28 H28 120.4
C29 C28 H28 120.4
C210 C29 C214 119.08(14)
C210 C29 C28 120.78(14)
C214 C29 C28 120.06(15)
O12 C110 C19 123.25(13)
O12 C110 C111 116.67(14)
C19 C110 C111 120.05(14)
O13 C111 C112 125.94(14)
O13 C111 C110 114.54(13)
C112 C111 C110 119.51(15)
C111 C112 C113 120.21(15)
C111 C112 H112 119.9
C113 C112 H112 119.9
C114 C113 C112 120.76(15)
C114 C113 H113 119.6
C112 C113 H113 119.6
C113 C114 C19 120.22(15)
C113 C114 H114 119.9
C19 C114 H114 119.9
O13 C115 H15A 109.5
O13 C115 H15B 109.5
H15A C115 H15B 109.5
O13 C115 H15C 109.5
H15A C115 H15C 109.5
H15B C115 H15C 109.5
O22 C210 C29 123.46(13)
O22 C210 C211 116.48(14)
C29 C210 C211 120.04(14)
O23 C211 C212 125.74(14)
O23 C211 C210 114.51(14)
C212 C211 C210 119.75(15)
C211 C212 C213 120.27(15)
C211 C212 H212 119.9
C213 C212 H212 119.9
C214 C213 C212 120.57(15)
C214 C213 H213 119.7
C212 C213 H213 119.7
C213 C214 C29 120.23(16)
C213 C214 H214 119.9
C29 C214 H214 119.9
O23 C215 H25A 109.5
O23 C215 H25B 109.5
H25A C215 H25B 109.5
O23 C215 H25C 109.5
H25A C215 H25C 109.5
H25B C215 H25C 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
N12 C18 1.291(2)
N12 N11 1.3765(17)
N11 C11 1.367(2)
N11 H11N 0.890(14)
N13 C15 1.374(2)
N13 H13A 0.893(15)
N13 H13B 0.890(14)
N21 N22 1.3713(17)
N21 C21 1.372(2)
N21 H21N 0.895(14)
N22 C28 1.2816(19)
N23 C25 1.382(2)
N23 H23B 0.892(15)
N23 H23A 0.893(15)
O1ME C1ME 1.421(2)
O1ME H1 0.863(15)
O2ME C2ME 1.417(2)
O2ME H2 0.864(15)
O11 C11 1.2396(18)
O12 C110 1.3570(18)
O12 H12O 0.856(14)
O13 C111 1.3723(18)
O13 C115 1.4292(19)
O21 C21 1.2401(18)
O22 C210 1.3618(18)
O22 H22 0.868(14)
O23 C211 1.378(2)
O23 C215 1.429(2)
C1ME H1ME 0.9800
C1ME H2ME 0.9800
C1ME H3ME 0.9800
C2ME H4ME 0.9800
C2ME H5ME 0.9800
C2ME H6ME 0.9800
C11 C12 1.471(2)
C12 C17 1.396(2)
C12 C13 1.404(2)
C13 C14 1.378(2)
C13 H13 0.9500
C14 C15 1.402(2)
C14 H14 0.9500
C15 C16 1.410(2)
C16 C17 1.382(2)
C16 H16 0.9500
C17 H17 0.9500
C18 C19 1.456(2)
C18 H18 0.9500
C19 C110 1.399(2)
C19 C114 1.410(2)
C21 C22 1.474(2)
C22 C27 1.399(2)
C22 C23 1.401(2)
C23 C24 1.376(2)
C23 H23 0.9500
C24 C25 1.399(2)
C24 H24 0.9500
C25 C26 1.405(2)
C26 C27 1.381(2)
C26 H26 0.9500
C27 H27 0.9500
C28 C29 1.455(2)
C28 H28 0.9500
C29 C210 1.403(2)
C29 C214 1.409(2)
C110 C111 1.414(2)
C111 C112 1.383(2)
C112 C113 1.399(2)
C112 H112 0.9500
C113 C114 1.370(2)
C113 H113 0.9500
C114 H114 0.9500
C115 H15A 0.9800
C115 H15B 0.9800
C115 H15C 0.9800
C210 C211 1.407(2)
C211 C212 1.383(2)
C212 C213 1.395(2)
C212 H212 0.9500
C213 C214 1.378(2)
C213 H213 0.9500
C214 H214 0.9500
C215 H25A 0.9800
C215 H25B 0.9800
C215 H25C 0.9800
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O12 H12O N12 0.856(14) 1.820(15) 2.5855(17) 147.9(17) .
C14 H14 O12 0.95 2.41 3.2456(19) 146.4 2_645
C24 H24 O22 0.95 2.52 3.361(2) 147.5 2_554
C215 H25A O12 0.98 2.64 3.591(2) 163.1 .
O1ME H1 O11 0.863(15) 1.809(15) 2.6627(16) 169(2) 2_655
O2ME H2 O21 0.864(15) 1.778(15) 2.6367(16) 172(2) 2_554
N11 H11N O1ME 0.890(14) 1.998(15) 2.8672(18) 165.0(19) 1_545
N13 H13A O12 0.893(15) 2.531(16) 3.345(2) 151.8(17) 2_645
N13 H13A O13 0.893(15) 2.481(17) 3.2566(19) 145.5(17) 2_645
N13 H13B O1ME 0.890(14) 2.276(15) 3.1500(19) 167.3(18) 3_665
N21 H21N O2ME 0.895(14) 1.975(15) 2.8472(18) 164.4(19) .
O22 H22 N21 0.868(14) 2.953(15) 3.8111(18) 170.1(17) .
O22 H22 N22 0.868(14) 1.765(16) 2.5702(17) 153.2(19) .
O22 H22 O21 0.868(14) 2.905(17) 3.6410(17) 143.7(16) .
N23 H23B O2ME 0.892(15) 2.262(15) 3.142(2) 168.8(18) 3_564
N23 H23A O22 0.893(15) 2.900(17) 3.691(2) 148.4(16) 2_554
N23 H23A O23 0.893(15) 2.431(16) 3.254(2) 153.3(17) 2_554
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
C18 N12 N11 C11 -172.44(14)
C21 N21 N22 C28 178.01(14)
N12 N11 C11 O11 -2.9(2)
N12 N11 C11 C12 175.39(12)
O11 C11 C12 C17 -26.1(2)
N11 C11 C12 C17 155.69(14)
O11 C11 C12 C13 152.65(15)
N11 C11 C12 C13 -25.6(2)
C17 C12 C13 C14 0.8(2)
C11 C12 C13 C14 -177.97(14)
C12 C13 C14 C15 -1.9(2)
C13 C14 C15 N13 179.50(14)
C13 C14 C15 C16 1.4(2)
N13 C15 C16 C17 -177.98(14)
C14 C15 C16 C17 0.1(2)
C15 C16 C17 C12 -1.2(2)
C13 C12 C17 C16 0.7(2)
C11 C12 C17 C16 179.49(14)
N11 N12 C18 C19 -177.51(13)
N12 C18 C19 C110 5.6(2)
N12 C18 C19 C114 -176.75(14)
N22 N21 C21 O21 -1.5(2)
N22 N21 C21 C22 178.89(13)
O21 C21 C22 C27 -25.4(2)
N21 C21 C22 C27 154.20(14)
O21 C21 C22 C23 155.80(15)
N21 C21 C22 C23 -24.6(2)
C27 C22 C23 C24 0.7(2)
C21 C22 C23 C24 179.60(14)
C22 C23 C24 C25 -1.5(2)
C23 C24 C25 N23 179.80(15)
C23 C24 C25 C26 1.4(2)
N23 C25 C26 C27 -179.02(15)
C24 C25 C26 C27 -0.6(2)
C25 C26 C27 C22 -0.1(2)
C23 C22 C27 C26 0.0(2)
C21 C22 C27 C26 -178.87(15)
N21 N22 C28 C29 -176.78(13)
N22 C28 C29 C210 1.4(2)
N22 C28 C29 C214 178.29(14)
C114 C19 C110 O12 -179.88(14)
C18 C19 C110 O12 -2.2(2)
C114 C19 C110 C111 -1.9(2)
C18 C19 C110 C111 175.79(14)
C115 O13 C111 C112 -2.4(2)
C115 O13 C111 C110 176.72(14)
O12 C110 C111 O13 -0.28(19)
C19 C110 C111 O13 -178.44(13)
O12 C110 C111 C112 178.89(13)
C19 C110 C111 C112 0.7(2)
O13 C111 C112 C113 179.69(14)
C110 C111 C112 C113 0.6(2)
C111 C112 C113 C114 -0.9(2)
C112 C113 C114 C19 -0.3(2)
C110 C19 C114 C113 1.6(2)
C18 C19 C114 C113 -176.04(14)
C214 C29 C210 O22 179.68(14)
C28 C29 C210 O22 -3.4(2)
C214 C29 C210 C211 -2.0(2)
C28 C29 C210 C211 174.83(14)
C215 O23 C211 C212 -2.2(2)
C215 O23 C211 C210 177.05(15)
O22 C210 C211 O23 -0.9(2)
C29 C210 C211 O23 -179.28(13)
O22 C210 C211 C212 178.38(14)
C29 C210 C211 C212 0.0(2)
O23 C211 C212 C213 -179.43(15)
C210 C211 C212 C213 1.4(2)
C211 C212 C213 C214 -0.7(2)
C212 C213 C214 C29 -1.4(2)
C210 C29 C214 C213 2.8(2)
C28 C29 C214 C213 -174.13(15)