#------------------------------------------------------------------------------
#$Date: 2018-02-14 06:18:34 +0200 (Wed, 14 Feb 2018) $
#$Revision: 206408 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/23/01/7230137.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_7230137
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_name_full               CrystEngComm
_journal_paper_doi               10.1039/C7CE02136D
_journal_year                    2018
_chemical_formula_moiety         'C14 H13 N3 O3, C H4 O'
_chemical_formula_sum            'C15 H17 N3 O4'
_chemical_formula_weight         303.32
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 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                 96.305(7)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.7634(6)
_cell_length_b                   19.3464(11)
_cell_length_c                   8.8479(7)
_cell_measurement_reflns_used    3062
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      31.7900
_cell_measurement_theta_min      4.6790
_cell_volume                     1491.00(18)
_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      296(2)
_diffrn_measured_fraction_theta_full 0.908
_diffrn_measured_fraction_theta_max 0.934
_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  0.0231
_diffrn_reflns_av_unetI/netI     0.0512
_diffrn_reflns_Laue_measured_fraction_full 0.934
_diffrn_reflns_Laue_measured_fraction_max 0.908
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            4751
_diffrn_reflns_point_group_measured_fraction_full 0.934
_diffrn_reflns_point_group_measured_fraction_max 0.908
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.498
_diffrn_reflns_theta_min         4.432
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.100
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.98216
_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    1.351
_exptl_crystal_description       prism
_exptl_crystal_F_000             640
_exptl_crystal_size_max          0.63
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.24
_refine_diff_density_max         0.157
_refine_diff_density_min         -0.146
_refine_diff_density_rms         0.032
_refine_ls_extinction_coef       0.059(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.016
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     211
_refine_ls_number_reflns         3114
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.016
_refine_ls_R_factor_all          0.0950
_refine_ls_R_factor_gt           0.0529
_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^)+(0.0536P)^2^+0.0834P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1132
_refine_ls_wR_factor_ref         0.1304
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1935
_reflns_number_total             3114
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c7ce02136d2.cif
_cod_data_source_block           2bMeOHexp2084
_cod_database_code               7230137
_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_2084 in P2(1)/n
CELL  0.71073   8.7634  19.3464   8.8479   90.000   96.305   90.000
ZERR     4.00   0.0006   0.0011   0.0007    0.000    0.007    0.000
LATT   1
SYMM  1/2 - X, 1/2 + Y, 1/2 - Z
SFAC  C    H    N    O
UNIT  60 68 12 16
MERG   2
OMIT    -1.00  55.00
omit 0 4 2
FMAP   2
PLAN   100
ACTA
BOND   $H
temp 23
dfix 0.86 n1 h11n
dfix 0.82 o4 h14o  o2 h12O
conf
EQIV $1 x+1, y, z
HTAB N1 O4_$1
HTAB O2 N1
HTAB O2 N2
HTAB O2 O1
HTAB O4 N3
EQIV $2 -x+1, -y, -z+2
HTAB C3 N3_$2
EQIV $3 -x+3/2, y+1/2, -z+3/2
HTAB C4 O2_$3
HTAB C4 O3_$3
EQIV $4 -x+2, -y, -z+2
HTAB C5 O2_$4
HTAB C7 O4_$1
EQIV $5 x+1/2, -y-1/2, z-1/2
HTAB C14 O2_$5
EQIV $6 -x+3/2, y-1/2, -z+3/2
HTAB C14 N3_$6
HTAB C14 O1_$5
HTAB C14 O4_$6
EQIV $7 -x+1, -y, -z+1
HTAB C15 O3_$7
HTAB C15 O2_$7
HTAB C15 O2_$3
HTAB C15 O3_$3
htab 3.0
L.S.   8
mpla  6 c2 c3 c4 c5 c6 n3
mpla 6  c8 c9 c10 c11 c12 c13
WGHT    0.053600    0.083400
EXTI    0.059370
FVAR       8.32831
N1    3    0.990812    0.009993    0.771122    11.00000    0.04009    0.04038 =
         0.06157   -0.01085    0.00626   -0.00085
H11N  2    1.050892    0.042556    0.807726    11.00000   -1.20000
N2    3    1.050800   -0.039584    0.683422    11.00000    0.04288    0.04072 =
         0.05399   -0.00548    0.00798    0.00358
N3    3    0.544924    0.104349    0.973521    11.00000    0.03999    0.05954 =
         0.07285   -0.00073    0.01336    0.00299
O1    4    0.759613   -0.042387    0.737130    11.00000    0.05020    0.05000 =
         0.10219   -0.01904    0.01103   -0.01066
O2    4    1.027109   -0.152017    0.518364    11.00000    0.03868    0.05946 =
         0.08238   -0.02207    0.01411   -0.00915
H12O  2    0.996750   -0.120167    0.569532    11.00000   -1.50000
O3    4    1.157557   -0.240590    0.348557    11.00000    0.05391    0.04894 =
         0.07327   -0.02024    0.00974   -0.00500

O4    4    0.224274    0.112703    0.872392    11.00000    0.03788    0.05889 =
         0.10297   -0.00998   -0.00430   -0.00306
H14O  2    0.313795    0.107499    0.915927    11.00000   -1.20000
C1    1    0.840261    0.004532    0.792781    11.00000    0.03988    0.03404 =
         0.05542    0.00382    0.00309   -0.00087
C2    1    0.777301    0.059067    0.888177    11.00000    0.03537    0.03852 =
         0.04674    0.00905    0.00392    0.00207
C3    1    0.620525    0.057680    0.899044    11.00000    0.04107    0.04755 =
         0.05925    0.00245    0.00673   -0.00282
AFIX  43
H3    2    0.564047    0.021664    0.851010    11.00000   -1.20000
AFIX   0
C4    1    0.628506    0.155102    1.043994    11.00000    0.05192    0.05588 =
         0.06993   -0.00502    0.01846    0.00896
AFIX  43
H4    2    0.578764    0.188651    1.095757    11.00000   -1.20000
AFIX   0
C5    1    0.784705    0.159689    1.043030    11.00000    0.04778    0.05787 =
         0.07722   -0.01671    0.01024   -0.00319
AFIX  43
H5    2    0.839097    0.195176    1.095423    11.00000   -1.20000
AFIX   0
C6    1    0.860417    0.111719    0.964468    11.00000    0.03496    0.05183 =
         0.06517   -0.00736    0.00786   -0.00116
AFIX  43
H6    2    0.966123    0.114574    0.962551    11.00000   -1.20000
AFIX   0
C7    1    1.191333   -0.034974    0.660487    11.00000    0.04472    0.03999 =
         0.05425   -0.00451    0.00442   -0.00537
AFIX  43
H7    2    1.249914    0.001796    0.702326    11.00000   -1.20000
AFIX   0
C8    1    1.261673   -0.086125    0.570158    11.00000    0.03866    0.03834 =
         0.04348    0.00216    0.00408   -0.00235
C9    1    1.176943   -0.141365    0.501893    11.00000    0.03321    0.04162 =
         0.04769    0.00298    0.00527   -0.00188
C10   1    1.249735   -0.188527    0.412007    11.00000    0.04412    0.03807 =
         0.04505    0.00148    0.00295   -0.00002
C11   1    1.402351   -0.180584    0.393052    11.00000    0.04616    0.04784 =
         0.05064    0.00297    0.01245    0.00756
AFIX  43
H11   2    1.449627   -0.211687    0.332951    11.00000   -1.20000
AFIX   0
C12   1    1.486256   -0.126289    0.463302    11.00000    0.03956    0.05888 =
         0.06259    0.00298    0.01497   -0.00398
AFIX  43
H12   2    1.589746   -0.121454    0.450971    11.00000   -1.20000
AFIX   0
C13   1    1.417225   -0.080015    0.550376    11.00000    0.04388    0.04905 =
         0.05433   -0.00158    0.00560   -0.00923
AFIX  43
H13   2    1.474444   -0.043925    0.597192    11.00000   -1.20000
AFIX   0
C14   1    1.229723   -0.294659    0.272749    11.00000    0.08099    0.05106 =
         0.07275   -0.01683    0.01663   -0.00185
AFIX 137
H14A  2    1.269614   -0.276370    0.184185    11.00000   -1.50000
H14B  2    1.155909   -0.330126    0.242862    11.00000   -1.50000
H14C  2    1.312186   -0.313848    0.340213    11.00000   -1.50000
AFIX   0
C15   1    0.216614    0.178687    0.804099    11.00000    0.06149    0.07164 =
         0.06841   -0.00795    0.01034    0.00109
AFIX 137
H15A  2    0.133875    0.204480    0.839338    11.00000   -1.50000
H15B  2    0.199174    0.173763    0.695611    11.00000   -1.50000
H15C  2    0.311581    0.202719    0.830877    11.00000   -1.50000

AFIX   0
HKLF    4

REM  exp_2084 in P2(1)/n
REM R1 =  0.0529 for    1935 Fo > 4sig(Fo)  and  0.0950 for all    3114 data
REM    211 parameters refined using      3 restraints

END

WGHT      0.0488      0.1123

REM Instructions for potential hydrogen bonds
HTAB N1 O4_$1
HTAB O2 N1
HTAB O2 N2
HTAB O2 O1
HTAB O4 N3
HTAB C3 N3_$2
HTAB C4 O2_$3
HTAB C4 O3_$3
HTAB C5 O2_$4
HTAB C7 O4_$1
HTAB C14 O2_$5
HTAB C14 N3_$6
HTAB C14 O1_$5
HTAB C14 O4_$6
HTAB C15 O3_$7
HTAB C15 O2_$7
HTAB C15 O2_$3
HTAB C15 O3_$3

REM Highest difference peak  0.157,  deepest hole -0.146,  1-sigma level  0.032
Q1    1   1.2033 -0.1007  0.5030  11.00000  0.05    0.16
Q2    1   1.3144 -0.0786  0.5272  11.00000  0.05    0.14
Q3    1   0.2364  0.2168  0.8834  11.00000  0.05    0.13
Q4    1   0.0822  0.2001  0.7433  11.00000  0.05    0.12
Q5    1   1.2417 -0.1270  0.5803  11.00000  0.05    0.12
Q6    1   0.8011  0.0941  0.8724  11.00000  0.05    0.12
Q7    1   1.4706 -0.1647  0.4836  11.00000  0.05    0.12
Q8    1   0.9873 -0.0831  0.6279  11.00000  0.05    0.12
Q9    1   0.8058 -0.0511  0.8486  11.00000  0.05    0.12
Q10   1   0.8140  0.0376  0.8372  11.00000  0.05    0.12
Q11   1   1.4709 -0.0586  0.6639  11.00000  0.05    0.11
Q12   1   0.8983  0.1888  1.1623  11.00000  0.05    0.11
Q13   1   1.4171 -0.1379  0.3617  11.00000  0.05    0.11
Q14   1   0.3336  0.1803  0.7402  11.00000  0.05    0.11
Q15   1   0.4323  0.1080  0.9635  11.00000  0.05    0.11
Q16   1   1.2190 -0.0707  0.6182  11.00000  0.05    0.11
Q17   1   1.2136 -0.1510  0.4409  11.00000  0.05    0.10
Q18   1   0.9351 -0.1897  0.4640  11.00000  0.05    0.10
Q19   1   1.6249 -0.1507  0.5098  11.00000  0.05    0.10
Q20   1   1.3373 -0.2872  0.2386  11.00000  0.05    0.10
Q21   1   1.3357 -0.1933  0.4612  11.00000  0.05    0.10
Q22   1   0.0956  0.1663  0.7720  11.00000  0.05    0.10
Q23   1   0.5932  0.0970  0.9034  11.00000  0.05    0.10
Q24   1   0.1163  0.1193  0.9054  11.00000  0.05    0.10
Q25   1   0.5272  0.0010  0.8615  11.00000  0.05    0.10
Q26   1   1.1589 -0.1170  0.3467  11.00000  0.05    0.10
Q27   1   0.1657  0.0659  0.9430  11.00000  0.05    0.10
Q28   1   0.5255  0.2528  0.9831  11.00000  0.05    0.10
Q29   1   1.0081 -0.2481  0.3779  11.00000  0.05    0.10
Q30   1   1.0836 -0.1332  0.4441  11.00000  0.05    0.10
Q31   1   0.9431 -0.0369  0.5034  11.00000  0.05    0.10
Q32   1   1.0018  0.1292  0.9083  11.00000  0.05    0.10
Q33   1   1.1209  0.0465  1.0024  11.00000  0.05    0.09
Q34   1   0.9803 -0.0518  0.6241  11.00000  0.05    0.09
Q35   1   0.7624 -0.0011  0.7269  11.00000  0.05    0.09
Q36   1   0.8348  0.0714  0.9539  11.00000  0.05    0.09
Q37   1   0.7369  0.0670  0.8535  11.00000  0.05    0.09
Q38   1   0.5659  0.1433  0.9396  11.00000  0.05    0.09
Q39   1   1.3125 -0.1732  0.3402  11.00000  0.05    0.09
Q40   1   0.4724  0.0631  1.0500  11.00000  0.05    0.09
Q41   1   0.6037  0.1083  1.0385  11.00000  0.05    0.09
Q42   1   1.4438 -0.1863  0.2388  11.00000  0.05    0.09
Q43   1   1.0249  0.0570  0.7564  11.00000  0.05    0.09
Q44   1   1.2835  0.0010  0.7228  11.00000  0.05    0.09
Q45   1   0.7177  0.1443  1.0775  11.00000  0.05    0.09
Q46   1   0.6320 -0.0405  0.7413  11.00000  0.05    0.09
Q47   1   0.4609  0.2031  1.0051  11.00000  0.05    0.09
Q48   1   1.0954 -0.0276  0.6150  11.00000  0.05    0.09
Q49   1   1.0419 -0.0821  0.7222  11.00000  0.05    0.09
Q50   1   0.3362  0.1162  0.8502  11.00000  0.05    0.09
Q51   1   0.9022  0.0134  0.7224  11.00000  0.05    0.08
Q52   1   1.4748 -0.2462  0.3085  11.00000  0.05    0.08
Q53   1   0.8568  0.2220  1.0413  11.00000  0.05    0.08
Q54   1   0.6278  0.1753  1.1710  11.00000  0.05    0.08
Q55   1   0.4938  0.1653  0.9856  11.00000  0.05    0.08
Q56   1   0.7339  0.0461  0.9346  11.00000  0.05    0.08
Q57   1   1.4229  0.0225  0.6691  11.00000  0.05    0.08
Q58   1   0.9530 -0.0004  0.6253  11.00000  0.05    0.08
Q59   1   1.1439 -0.3109  0.1552  11.00000  0.05    0.08
Q60   1   1.4449 -0.0989  0.4708  11.00000  0.05    0.08
Q61   1   1.6187 -0.1087  0.3993  11.00000  0.05    0.08
Q62   1   1.1000  0.0636  0.8545  11.00000  0.05    0.08
Q63   1   1.3830 -0.2514  0.1732  11.00000  0.05    0.08
Q64   1   0.9423  0.2358  1.1026  11.00000  0.05    0.08
Q65   1   0.9801  0.2290  1.0986  11.00000  0.05    0.08
Q66   1   1.2588 -0.0332  0.8255  11.00000  0.05    0.08
Q67   1   1.1039 -0.2146  0.2460  11.00000  0.05    0.08
Q68   1   0.9508 -0.2029  0.5531  11.00000  0.05    0.08
Q69   1   1.5414 -0.2681  0.2573  11.00000  0.05    0.07
Q70   1   0.9498 -0.0054  0.8330  11.00000  0.05    0.07
Q71   1   0.6787 -0.0540  0.8180  11.00000  0.05    0.07
Q72   1   1.1343 -0.0508  0.7186  11.00000  0.05    0.07
Q73   1   0.1149  0.1030  0.6974  11.00000  0.05    0.07
Q74   1   1.5843 -0.2018  0.5555  11.00000  0.05    0.07
Q75   1   0.2956  0.1564  0.6461  11.00000  0.05    0.07
Q76   1   0.4573  0.1322  1.0483  11.00000  0.05    0.07
Q77   1   1.4321 -0.1924  0.5789  11.00000  0.05    0.07
Q78   1   0.0007  0.2306  0.7794  11.00000  0.05    0.07
Q79   1   0.8962 -0.1517  0.4775  11.00000  0.05    0.07
Q80   1   1.0405 -0.2096  0.3114  11.00000  0.05    0.07
Q81   1   1.2543  0.0112  0.6689  11.00000  0.05    0.07
Q82   1   1.0832 -0.2428  0.0954  11.00000  0.05    0.07
Q83   1   0.9972  0.0489  1.0006  11.00000  0.05    0.07
Q84   1   0.9795  0.1548  0.8035  11.00000  0.05    0.07
Q85   1   1.0322 -0.0724  0.4486  11.00000  0.05    0.07
Q86   1   0.9571 -0.1378  0.3833  11.00000  0.05    0.07
Q87   1   1.0368 -0.0247  0.9201  11.00000  0.05    0.07
Q88   1   0.7970  0.1525  0.9218  11.00000  0.05    0.07
Q89   1   0.6105 -0.0118  0.8889  11.00000  0.05    0.07
Q90   1   1.3849 -0.0574  0.7805  11.00000  0.05    0.07
Q91   1   1.5295 -0.1244  0.4558  11.00000  0.05    0.07
Q92   1   0.8985 -0.0505  0.6935  11.00000  0.05    0.07
Q93   1   1.2322 -0.2027  0.4035  11.00000  0.05    0.07
Q94   1   0.4551  0.2514  0.8728  11.00000  0.05    0.07
Q95   1   0.4759 -0.0333  0.8625  11.00000  0.05    0.06
Q96   1   1.1920 -0.2028  0.3491  11.00000  0.05    0.06
Q97   1   0.8331  0.0367  1.0602  11.00000  0.05    0.06
Q98   1   1.3897 -0.0180  0.5905  11.00000  0.05    0.06
Q99   1   1.0146  0.0861  1.0416  11.00000  0.05    0.06
Q100  1   1.3891 -0.3530  0.4541  11.00000  0.05    0.06
;
_shelx_res_checksum              24756
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -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
N1 N 0.99081(18) 0.00999(9) 0.77112(19) 0.0473(4) Uani 1 1 d D .
H11N H 1.051(2) 0.0426(10) 0.808(2) 0.057 Uiso 1 1 d D U
N2 N 1.05080(18) -0.03958(8) 0.68342(18) 0.0457(4) Uani 1 1 d . .
N3 N 0.54492(18) 0.10435(10) 0.9735(2) 0.0569(5) Uani 1 1 d . .
O1 O 0.75961(16) -0.04239(8) 0.7371(2) 0.0673(5) Uani 1 1 d . .
O2 O 1.02711(16) -0.15202(8) 0.51836(18) 0.0596(4) Uani 1 1 d D .
H12O H 0.997(3) -0.1202(12) 0.570(3) 0.089 Uiso 1 1 d D U
O3 O 1.15756(16) -0.24059(8) 0.34856(17) 0.0585(4) Uani 1 1 d . .
O4 O 0.22427(16) 0.11270(8) 0.8724(2) 0.0675(5) Uani 1 1 d D .
H14O H 0.314(2) 0.1075(14) 0.916(3) 0.081 Uiso 1 1 d D U
C1 C 0.8403(2) 0.00453(10) 0.7928(2) 0.0433(5) Uani 1 1 d . .
C2 C 0.7773(2) 0.05907(10) 0.8882(2) 0.0403(5) Uani 1 1 d . .
C3 C 0.6205(2) 0.05768(11) 0.8990(2) 0.0492(5) Uani 1 1 d . .
H3 H 0.5640 0.0217 0.8510 0.059 Uiso 1 1 calc R U
C4 C 0.6285(2) 0.15510(12) 1.0440(3) 0.0584(6) Uani 1 1 d . .
H4 H 0.5788 0.1887 1.0958 0.070 Uiso 1 1 calc R U
C5 C 0.7847(2) 0.15969(12) 1.0430(3) 0.0607(6) Uani 1 1 d . .
H5 H 0.8391 0.1952 1.0954 0.073 Uiso 1 1 calc R U
C6 C 0.8604(2) 0.11172(11) 0.9645(2) 0.0505(5) Uani 1 1 d . .
H6 H 0.9661 0.1146 0.9626 0.061 Uiso 1 1 calc R U
C7 C 1.1913(2) -0.03497(10) 0.6605(2) 0.0464(5) Uani 1 1 d . .
H7 H 1.2499 0.0018 0.7023 0.056 Uiso 1 1 calc R U
C8 C 1.2617(2) -0.08613(10) 0.5702(2) 0.0402(5) Uani 1 1 d . .
C9 C 1.1769(2) -0.14136(10) 0.5019(2) 0.0408(5) Uani 1 1 d . .
C10 C 1.2497(2) -0.18853(10) 0.4120(2) 0.0426(5) Uani 1 1 d . .
C11 C 1.4024(2) -0.18058(11) 0.3931(2) 0.0477(5) Uani 1 1 d . .
H11 H 1.4496 -0.2117 0.3330 0.057 Uiso 1 1 calc R U
C12 C 1.4863(2) -0.12629(12) 0.4633(2) 0.0530(6) Uani 1 1 d . .
H12 H 1.5897 -0.1215 0.4510 0.064 Uiso 1 1 calc R U
C13 C 1.4172(2) -0.08001(11) 0.5504(2) 0.0491(5) Uani 1 1 d . .
H13 H 1.4744 -0.0439 0.5972 0.059 Uiso 1 1 calc R U
C14 C 1.2297(3) -0.29466(13) 0.2727(3) 0.0677(7) Uani 1 1 d . .
H14A H 1.2696 -0.2764 0.1842 0.101 Uiso 1 1 calc R U
H14B H 1.1559 -0.3301 0.2429 0.101 Uiso 1 1 calc R U
H14C H 1.3122 -0.3138 0.3402 0.101 Uiso 1 1 calc R U
C15 C 0.2166(3) 0.17869(14) 0.8041(3) 0.0669(7) Uani 1 1 d . .
H15A H 0.1339 0.2045 0.8393 0.100 Uiso 1 1 calc R U
H15B H 0.1992 0.1738 0.6956 0.100 Uiso 1 1 calc R U
H15C H 0.3116 0.2027 0.8309 0.100 Uiso 1 1 calc R 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
N1 0.0401(10) 0.0404(10) 0.0616(11) -0.0108(8) 0.0063(8) -0.0009(7)
N2 0.0429(10) 0.0407(10) 0.0540(10) -0.0055(8) 0.0080(8) 0.0036(7)
N3 0.0400(10) 0.0595(12) 0.0728(12) -0.0007(10) 0.0134(8) 0.0030(8)
O1 0.0502(9) 0.0500(10) 0.1022(13) -0.0190(8) 0.0110(8) -0.0107(7)
O2 0.0387(8) 0.0595(10) 0.0824(11) -0.0221(8) 0.0141(7) -0.0092(6)
O3 0.0539(9) 0.0489(9) 0.0733(10) -0.0202(8) 0.0097(7) -0.0050(6)
O4 0.0379(9) 0.0589(11) 0.1030(13) -0.0100(9) -0.0043(8) -0.0031(7)
C1 0.0399(11) 0.0340(11) 0.0554(12) 0.0038(9) 0.0031(9) -0.0009(8)
C2 0.0354(10) 0.0385(11) 0.0467(11) 0.0090(9) 0.0039(8) 0.0021(8)
C3 0.0411(12) 0.0475(12) 0.0592(13) 0.0025(10) 0.0067(9) -0.0028(9)
C4 0.0519(14) 0.0559(14) 0.0699(15) -0.0050(12) 0.0185(11) 0.0090(10)
C5 0.0478(13) 0.0579(15) 0.0772(16) -0.0167(12) 0.0102(11) -0.0032(10)
C6 0.0350(11) 0.0518(13) 0.0652(13) -0.0074(11) 0.0079(9) -0.0012(8)
C7 0.0447(12) 0.0400(11) 0.0543(12) -0.0045(9) 0.0044(9) -0.0054(8)
C8 0.0387(11) 0.0383(11) 0.0435(11) 0.0022(8) 0.0041(8) -0.0024(8)
C9 0.0332(10) 0.0416(11) 0.0477(11) 0.0030(9) 0.0053(8) -0.0019(7)
C10 0.0441(12) 0.0381(11) 0.0451(11) 0.0015(9) 0.0030(9) 0.0000(8)
C11 0.0462(12) 0.0478(13) 0.0506(12) 0.0030(9) 0.0124(9) 0.0076(9)
C12 0.0396(12) 0.0589(15) 0.0626(14) 0.0030(11) 0.0150(10) -0.0040(9)
C13 0.0439(12) 0.0491(13) 0.0543(13) -0.0016(10) 0.0056(9) -0.0092(9)
C14 0.0810(17) 0.0511(15) 0.0728(16) -0.0168(12) 0.0166(13) -0.0019(11)
C15 0.0615(15) 0.0716(18) 0.0684(16) -0.0080(13) 0.0103(11) 0.0011(12)
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
C1 N1 N2 117.60(16)
C1 N1 H11N 124.6(15)
N2 N1 H11N 117.8(15)
C7 N2 N1 118.55(16)
C3 N3 C4 116.76(17)
C9 O2 H12O 108.7(18)
C10 O3 C14 117.32(16)
C15 O4 H14O 107.6(18)
O1 C1 N1 121.97(19)
O1 C1 C2 121.31(18)
N1 C1 C2 116.72(16)
C6 C2 C3 116.89(18)
C6 C2 C1 126.01(17)
C3 C2 C1 117.08(17)
N3 C3 C2 124.71(19)
N3 C3 H3 117.6
C2 C3 H3 117.6
N3 C4 C5 122.7(2)
N3 C4 H4 118.7
C5 C4 H4 118.7
C4 C5 C6 119.8(2)
C4 C5 H5 120.1
C6 C5 H5 120.1
C5 C6 C2 119.11(18)
C5 C6 H6 120.4
C2 C6 H6 120.4
N2 C7 C8 121.12(18)
N2 C7 H7 119.4
C8 C7 H7 119.4
C13 C8 C9 119.26(18)
C13 C8 C7 119.35(17)
C9 C8 C7 121.39(17)
O2 C9 C8 123.02(17)
O2 C9 C10 117.86(16)
C8 C9 C10 119.11(17)
O3 C10 C11 124.69(18)
O3 C10 C9 115.08(16)
C11 C10 C9 120.24(17)
C10 C11 C12 120.28(19)
C10 C11 H11 119.9
C12 C11 H11 119.9
C13 C12 C11 120.19(18)
C13 C12 H12 119.9
C11 C12 H12 119.9
C12 C13 C8 120.91(18)
C12 C13 H13 119.5
C8 C13 H13 119.5
O3 C14 H14A 109.5
O3 C14 H14B 109.5
H14A C14 H14B 109.5
O3 C14 H14C 109.5
H14A C14 H14C 109.5
H14B C14 H14C 109.5
O4 C15 H15A 109.5
O4 C15 H15B 109.5
H15A C15 H15B 109.5
O4 C15 H15C 109.5
H15A C15 H15C 109.5
H15B C15 H15C 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
N1 C1 1.358(2)
N1 N2 1.374(2)
N1 H11N 0.861(15)
N2 C7 1.273(2)
N3 C3 1.336(3)
N3 C4 1.338(3)
O1 C1 1.220(2)
O2 C9 1.353(2)
O2 H12O 0.826(17)
O3 C10 1.372(2)
O3 C14 1.427(3)
O4 C15 1.411(3)
O4 H14O 0.841(16)
C1 C2 1.494(3)
C2 C6 1.384(3)
C2 C3 1.388(2)
C3 H3 0.9300
C4 C5 1.373(3)
C4 H4 0.9300
C5 C6 1.373(3)
C5 H5 0.9300
C6 H6 0.9300
C7 C8 1.451(3)
C7 H7 0.9300
C8 C13 1.398(2)
C8 C9 1.400(3)
C9 C10 1.408(3)
C10 C11 1.375(2)
C11 C12 1.389(3)
C11 H11 0.9300
C12 C13 1.365(3)
C12 H12 0.9300
C13 H13 0.9300
C14 H14A 0.9600
C14 H14B 0.9600
C14 H14C 0.9600
C15 H15A 0.9600
C15 H15B 0.9600
C15 H15C 0.9600
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
N1 H11N O4 0.861(15) 2.070(16) 2.921(2) 170(2) 1_655
O2 H12O N2 0.826(17) 1.89(2) 2.615(2) 146(2) .
O4 H14O N3 0.841(16) 2.035(17) 2.858(2) 166(2) .
C4 H4 O3 0.93 2.57 3.433(3) 153.6 2_656
C6 H6 O4 0.93 2.48 3.377(3) 161.9 1_655
C7 H7 O4 0.93 2.64 3.412(3) 140.3 1_655
C13 H13 O1 0.93 2.67 3.343(2) 130.4 1_655
C14 H14B O1 0.96 2.63 3.182(3) 116.8 4_655
C15 H15B O2 0.96 2.62 3.410(3) 139.7 3_656
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
C1 N1 N2 C7 179.29(18)
N2 N1 C1 O1 0.0(3)
N2 N1 C1 C2 -179.86(16)
O1 C1 C2 C6 175.5(2)
N1 C1 C2 C6 -4.6(3)
O1 C1 C2 C3 -5.8(3)
N1 C1 C2 C3 174.04(18)
C4 N3 C3 C2 -1.1(3)
C6 C2 C3 N3 2.1(3)
C1 C2 C3 N3 -176.73(19)
C3 N3 C4 C5 -0.8(3)
N3 C4 C5 C6 1.5(4)
C4 C5 C6 C2 -0.4(3)
C3 C2 C6 C5 -1.2(3)
C1 C2 C6 C5 177.47(19)
N1 N2 C7 C8 179.37(18)
N2 C7 C8 C13 -178.63(18)
N2 C7 C8 C9 1.6(3)
C13 C8 C9 O2 178.34(17)
C7 C8 C9 O2 -1.9(3)
C13 C8 C9 C10 -1.5(3)
C7 C8 C9 C10 178.30(17)
C14 O3 C10 C11 7.8(3)
C14 O3 C10 C9 -172.18(18)
O2 C9 C10 O3 0.8(3)
C8 C9 C10 O3 -179.43(16)
O2 C9 C10 C11 -179.21(17)
C8 C9 C10 C11 0.6(3)
O3 C10 C11 C12 -179.49(19)
C9 C10 C11 C12 0.5(3)
C10 C11 C12 C13 -0.7(3)
C11 C12 C13 C8 -0.2(3)
C9 C8 C13 C12 1.3(3)
C7 C8 C13 C12 -178.5(2)