#------------------------------------------------------------------------------
#$Date: 2024-10-30 04:36:46 +0200 (Wed, 30 Oct 2024) $
#$Revision: 295676 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/57/29/1572976.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_1572976
loop_
_publ_author_name
'Fu, Shijie'
'Jia, Hao'
'Meng, Xinmiao'
'Wang, Chengyuan'
'Li, Qian'
'Li, Lei'
'Yang, Jiaxiang'
'Niu, Helin'
_publ_section_title
;
Fine-tuning the molecular conformation and packing structures of
coumarin-based luminogens to achieve distinct piezochromic properties
upon mechanical grinding and under hydrostatic pressures.
;
_journal_name_full 'Materials horizons'
_journal_paper_doi 10.1039/d4mh01343c
_journal_year 2024
_chemical_formula_moiety 'C20 H21 N O3'
_chemical_formula_sum 'C20 H21 N O3'
_chemical_formula_weight 323.38
_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'
_atom_sites_solution_hydrogens geom
_atom_sites_solution_primary dual
_audit_creation_date 2024-10-12
_audit_creation_method
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_audit_update_record
;
2024-10-13 deposited with the CCDC. 2024-10-22 downloaded from the CCDC.
;
_cell_angle_alpha 90
_cell_angle_beta 90.73(2)
_cell_angle_gamma 90
_cell_formula_units_Z 4
_cell_length_a 6.4917(18)
_cell_length_b 19.911(6)
_cell_length_c 12.759(4)
_cell_measurement_reflns_used 1362
_cell_measurement_temperature 150
_cell_measurement_theta_max 30.04
_cell_measurement_theta_min 4.01
_cell_volume 1649.0(9)
_computing_cell_refinement
;
X-Area Recipe 1.33.0.0 (STOE, 2015)
;
_computing_data_collection
;
X-Area Pilatus3_SV 1.31.153.0 (STOE, 2018)
;
_computing_data_reduction
;
X-Area Integrate 1.74.2.0 (STOE, 2018)
X-Area LANA 1.75.3.0 (STOE, 2018)
;
_computing_molecular_graphics 'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material
;
STOE & Cie GmbH, X-Area, software package for collecting single-crystal or
multi-domain crystal data on STOE area-detector diffractometers, for image
processing, for the correction and scaling of reflection intensities and
for outlier rejection, version 1.86, Darmstadt 2018
;
_computing_structure_refinement 'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution 'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature 150
_diffrn_detector Pilatus300K
_diffrn_detector_area_resol_mean 5.81
_diffrn_detector_type 'DECTRIS PILATUS 300K'
_diffrn_measured_fraction_theta_full 0.985
_diffrn_measured_fraction_theta_max 0.978
_diffrn_measurement_details
;
1827 frames, detector distance = 50 mm
;
_diffrn_measurement_device 'Eulerian 4-circle diffractometer'
_diffrn_measurement_device_type 'STOE STADIVARI'
_diffrn_measurement_method 'rotation method, \w scans'
_diffrn_radiation_collimation '1.2 mm, 0.6 diameter'
_diffrn_radiation_monochromator 'Graded multilayer mirror'
_diffrn_radiation_polarisn_norm 270
_diffrn_radiation_probe x-ray
_diffrn_radiation_type 'Cu K\a'
_diffrn_radiation_wavelength 1.54186
_diffrn_reflns_av_R_equivalents 0.0273
_diffrn_reflns_av_unetI/netI 0.0238
_diffrn_reflns_Laue_measured_fraction_full 0.985
_diffrn_reflns_Laue_measured_fraction_max 0.978
_diffrn_reflns_limit_h_max 7
_diffrn_reflns_limit_h_min -5
_diffrn_reflns_limit_k_max 23
_diffrn_reflns_limit_k_min -23
_diffrn_reflns_limit_l_max 12
_diffrn_reflns_limit_l_min -15
_diffrn_reflns_number 14629
_diffrn_reflns_point_group_measured_fraction_full 0.985
_diffrn_reflns_point_group_measured_fraction_max 0.978
_diffrn_reflns_theta_full 67.686
_diffrn_reflns_theta_max 68.292
_diffrn_reflns_theta_min 4.116
_diffrn_source 'GeniX 3D HF Cu'
_diffrn_source_current 0.600
_diffrn_source_power 0.030
_diffrn_source_voltage 50
_exptl_absorpt_coefficient_mu 0.703
_exptl_absorpt_correction_T_max 1.0000
_exptl_absorpt_correction_T_min 0.3133
_exptl_absorpt_correction_type multi-scan
_exptl_absorpt_process_details
;
STOE LANA, absorption correction by scaling of reflection intensities.
J. Koziskova, F. Hahn, J. Richter, J. Kozisek, "Comparison of different
absorption corrections on the model structure of tetrakis(\m~2~-acetato)-
diaqua-di-copper(II)", Acta Chimica Slovaca, vol. 9, no. 2, 2016, pp. 136 - 140.
;
_exptl_crystal_colour Yellow
_exptl_crystal_density_diffrn 1.303
_exptl_crystal_density_method 'not measured'
_exptl_crystal_description Block
_exptl_crystal_F_000 688
_exptl_crystal_size_max 0.5
_exptl_crystal_size_mid 0.3
_exptl_crystal_size_min 0.1
_refine_diff_density_max 0.132
_refine_diff_density_min -0.172
_refine_diff_density_rms 0.038
_refine_ls_extinction_method none
_refine_ls_goodness_of_fit_ref 1.017
_refine_ls_hydrogen_treatment constr
_refine_ls_matrix_type full
_refine_ls_number_parameters 220
_refine_ls_number_reflns 2958
_refine_ls_number_restraints 0
_refine_ls_restrained_S_all 1.017
_refine_ls_R_factor_all 0.0517
_refine_ls_R_factor_gt 0.0343
_refine_ls_shift/su_max 0.001
_refine_ls_shift/su_mean 0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0469P)^2^+0.1531P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme calc
_refine_ls_wR_factor_gt 0.0788
_refine_ls_wR_factor_ref 0.0857
_reflns_Friedel_coverage 0.000
_reflns_number_gt 2248
_reflns_number_total 2958
_reflns_threshold_expression 'I > 2\s(I)'
_cod_data_source_file d4mh01343c3.cif
_cod_data_source_block 2
_cod_original_cell_volume 1649.0(8)
_cod_database_code 1572976
_shelx_shelxl_version_number 2018/3
_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.
;
_olex2_refinement_description
;
1. Fixed Uiso
At 1.2 times of:
All C(H) groups, All C(H,H) groups
At 1.5 times of:
All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
C00K(H00D,H00F), C00L(H00K,H00L)
2.b Aromatic/amide H refined with riding coordinates:
C00A(H00A), C00B(H00B), C00C(H00C), C00E(H00E), C00G(H00G), C00H(H00H),
C00I(H00I), C00J(H00J)
2.c Idealised Me refined as rotating group:
C00M(H00M,H00N,H00O), C00N(H00P,H00Q,H00R), C00O(H00S,H00T,H00U)
;
_shelx_res_file
;
TITL 2_a.res in P2(1)/n
2.res
created by SHELXL-2018/3 at 20:26:15 on 12-Oct-2024
REM Old TITL
REM SHELXT solution in P2(1)/n
REM R1 0.122, Rweak 0.004, Alpha 0.021, Orientation as input
REM Formula found by SHELXT: C20 N O3
CELL 1.54186 6.4917 19.9107 12.7585 90 90.731 90
ZERR 4 0.0018 0.0064 0.0035 0 0.022 0
LATT 1
SYMM 0.5-X,0.5+Y,0.5-Z
SFAC C H N O
UNIT 80 84 4 12
L.S. 4 0 0
PLAN 5
TEMP -153.15
CONF
list 4
fmap 2 53
acta
MORE -1
BOND $H
REM
REM
REM
WGHT 0.046900 0.153100
FVAR 0.51453
O001 4 0.404564 0.607540 0.520517 11.00000 0.02135 0.02769 =
0.02621 0.00378 0.00325 0.00240
O002 4 0.264581 0.564896 0.660310 11.00000 0.02364 0.03884 =
0.03546 0.00872 0.00699 0.00364
O003 4 0.761058 0.407960 1.024378 11.00000 0.03567 0.04460 =
0.02608 0.00987 0.00016 -0.00268
N004 3 0.661514 0.723540 0.223924 11.00000 0.02834 0.02970 =
0.03021 0.00701 0.00442 0.00045
C005 1 0.622025 0.540544 0.637442 11.00000 0.02368 0.01988 =
0.02479 -0.00385 0.00101 -0.00117
C006 1 0.568583 0.622037 0.457751 11.00000 0.02273 0.02239 =
0.02411 -0.00373 0.00401 -0.00171
C007 1 0.421490 0.569324 0.610888 11.00000 0.02438 0.02160 =
0.02493 -0.00093 0.00218 -0.00057
C008 1 0.649564 0.503272 0.737351 11.00000 0.02583 0.02055 =
0.02409 -0.00250 0.00305 0.00132
C009 1 0.761226 0.594982 0.482078 11.00000 0.02273 0.02467 =
0.02534 -0.00211 0.00088 -0.00008
C00A 1 0.780705 0.553622 0.572369 11.00000 0.02180 0.02552 =
0.02611 -0.00249 0.00052 0.00177
AFIX 43
H00A 2 0.911181 0.534177 0.587939 11.00000 -1.20000
AFIX 0
C00B 1 0.530943 0.664228 0.374413 11.00000 0.02451 0.02358 =
0.02775 -0.00003 0.00050 0.00228
AFIX 43
H00B 2 0.396024 0.681084 0.361684 11.00000 -1.20000
AFIX 0
C00C 1 0.490838 0.468583 0.786204 11.00000 0.02627 0.02351 =
0.02875 -0.00086 -0.00064 -0.00165
AFIX 43
H00C 2 0.358377 0.467302 0.753744 11.00000 -1.20000
AFIX 0
C00D 1 0.692534 0.682243 0.308349 11.00000 0.02945 0.02223 =
0.02513 -0.00104 0.00030 -0.00098
C00E 1 0.843035 0.502811 0.787642 11.00000 0.02393 0.02769 =
0.02732 0.00055 0.00272 -0.00124
AFIX 43
H00E 2 0.954789 0.525607 0.756025 11.00000 -1.20000
AFIX 0
C00F 1 0.713679 0.436909 0.929728 11.00000 0.03279 0.02556 =
0.02336 0.00006 0.00258 0.00246
C00G 1 0.875267 0.470175 0.881673 11.00000 0.02546 0.03270 =
0.02735 -0.00060 -0.00120 0.00032
AFIX 43
H00G 2 1.008179 0.470416 0.913705 11.00000 -1.20000
AFIX 0
C00H 1 0.521903 0.435843 0.881259 11.00000 0.02706 0.02561 =
0.03014 0.00092 0.00535 -0.00350
AFIX 43
H00H 2 0.411108 0.412657 0.913059 11.00000 -1.20000
AFIX 0
C00I 1 0.921716 0.612930 0.415218 11.00000 0.02225 0.03485 =
0.03062 0.00238 0.00150 0.00192
AFIX 43
H00I 2 1.055901 0.595540 0.428216 11.00000 -1.20000
AFIX 0
C00J 1 0.889767 0.654944 0.331572 11.00000 0.02510 0.03482 =
0.02878 0.00325 0.00562 -0.00266
AFIX 43
H00J 2 1.002406 0.666075 0.288050 11.00000 -1.20000
AFIX 0
C00K 1 0.833619 0.753104 0.168068 11.00000 0.03432 0.02895 =
0.03605 0.00784 0.00470 -0.00310
AFIX 23
H00D 2 0.949883 0.759892 0.217914 11.00000 -1.20000
H00F 2 0.791749 0.797744 0.141073 11.00000 -1.20000
AFIX 0
C00L 1 0.458137 0.748589 0.195265 11.00000 0.03217 0.03477 =
0.02980 0.00913 -0.00148 -0.00036
AFIX 23
H00K 2 0.355267 0.712902 0.208024 11.00000 -1.20000
H00L 2 0.455009 0.758957 0.119372 11.00000 -1.20000
AFIX 0
C00M 1 0.600669 0.374458 1.077807 11.00000 0.04705 0.04198 =
0.02801 0.00895 0.00268 -0.00793
AFIX 137
H00M 2 0.552613 0.336198 1.035815 11.00000 -1.50000
H00N 2 0.486126 0.405640 1.088724 11.00000 -1.50000
H00O 2 0.652451 0.358389 1.145798 11.00000 -1.50000
AFIX 0
C00N 1 0.906344 0.710583 0.077572 11.00000 0.04283 0.04778 =
0.03520 0.00539 0.01066 -0.00274
AFIX 137
H00P 2 0.794148 0.705489 0.026065 11.00000 -1.50000
H00Q 2 0.948001 0.666242 0.103580 11.00000 -1.50000
H00R 2 1.024015 0.732461 0.044421 11.00000 -1.50000
AFIX 0
C00O 1 0.397515 0.811186 0.255969 11.00000 0.03729 0.03243 =
0.05215 0.00949 0.00318 0.00551
AFIX 137
H00S 2 0.260019 0.825863 0.233126 11.00000 -1.50000
H00T 2 0.497315 0.847038 0.242777 11.00000 -1.50000
H00U 2 0.396173 0.800968 0.331095 11.00000 -1.50000
AFIX 0
HKLF 4
REM 2_a.res in P2(1)/n
REM wR2 = 0.0857, GooF = S = 1.017, Restrained GooF = 1.017 for all data
REM R1 = 0.0343 for 2248 Fo > 4sig(Fo) and 0.0517 for all 2958 data
REM 220 parameters refined using 0 restraints
END
WGHT 0.0469 0.1531
REM Highest difference peak 0.132, deepest hole -0.172, 1-sigma level 0.038
Q1 1 0.9846 0.6426 0.2547 11.00000 0.05 0.13
Q2 1 0.6605 0.5951 0.4602 11.00000 0.05 0.13
Q3 1 0.6793 0.6205 0.4912 11.00000 0.05 0.12
Q4 1 0.7063 0.5631 0.6261 11.00000 0.05 0.12
Q5 1 0.9908 0.5057 0.9278 11.00000 0.05 0.12
;
_shelx_res_checksum 25007
_olex2_submission_special_instructions 'No special instructions were received'
_stoe_detector_distance '50.0 mm'
_stoe_detector_pixelsize_x '0.172 mm'
_stoe_detector_pixelsize_y '0.172 mm'
_stoe_detector_size_x '8.4 cm'
_stoe_detector_size_y '10.6 cm'
_stoe_evaluation_integration_a 6.0
_stoe_evaluation_integration_b 0.5
_stoe_evaluation_integration_ems 0.020
_stoe_evaluation_lana_bis_l_even_max -
_stoe_evaluation_lana_bis_l_odd_max -
_stoe_evaluation_lana_bos_l_even_max 4
_stoe_evaluation_lana_bos_l_odd_max 1
_stoe_evaluation_lana_completeness 94.9
_stoe_evaluation_lana_dxs_max_order 3
_stoe_evaluation_lana_dys_max_order 3
_stoe_evaluation_lana_fs_max_order 3
_stoe_evaluation_lana_max_2theta_available 137.1
_stoe_evaluation_lana_max_2theta_desired 137.1
_stoe_evaluation_lana_mean_redundancy 2.4
_stoe_evaluation_lana_number_refls_after_or 13590
_stoe_evaluation_lana_number_refls_outliers 1742
_stoe_evaluation_lana_number_refls_total 15332
_stoe_evaluation_lana_number_refls_unique 5776
_stoe_evaluation_lana_number_refls_written 13590
_stoe_evaluation_lana_or_c1 0.035
_stoe_evaluation_lana_or_c2 0
_stoe_evaluation_lana_or_c3 0
_stoe_evaluation_lana_or_c4 0.7
_stoe_evaluation_lana_point_group -1
_stoe_evaluation_lana_table
;
#----------------------------------------------------------------------------
2Theta 15.1 29.5 43.9 58.3 72.7 87.1 101.5 115.9 130.3
#----------------------------------------------------------------------------
5.11 2.90 2.03 1.54 1.29 1.12 1.00 0.91 0.86
N(total) 111 347 673 1662 3455 2850 2725 2325 1184
2.0 1.8 1.7 2.5 3.4 2.6 2.3 2.0 1.7
Complet. [%%] 100.0 96.8 97.9 99.1 100.0 99.9 99.3 97.8 72.6
151.8 89.0 40.0 19.3 14.2 13.6 9.7 6.9 7.2
R(int) 0.007 0.009 0.016 0.020 0.021 0.021 0.030 0.047 0.048
#----------------------------------------------------------------------------
;
_stoe_measurement_identifier 2
_stoe_measurement_max_exposure_per_frame '3.0 s'
_stoe_measurement_mean_exposure_per_frame '2.5 s'
_stoe_measurement_min_exposure_per_frame '1.0 s'
_stoe_measurement_total_exposure_time '74 min'
_stoe_measurement_total_frame_number 1760
_stoe_measurement_total_run_number 27
_stoe_measurement_tube_power '30.0 W'
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
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O001 O 0.40456(14) 0.60754(4) 0.52052(7) 0.0251(2) Uani 1 1 d . . . . .
O002 O 0.26458(15) 0.56490(5) 0.66031(7) 0.0326(2) Uani 1 1 d . . . . .
O003 O 0.76106(16) 0.40796(5) 1.02438(7) 0.0355(3) Uani 1 1 d . . . . .
N004 N 0.66151(18) 0.72354(6) 0.22392(9) 0.0294(3) Uani 1 1 d . . . . .
C005 C 0.6220(2) 0.54054(6) 0.63744(10) 0.0228(3) Uani 1 1 d . . . . .
C006 C 0.5686(2) 0.62204(6) 0.45775(10) 0.0230(3) Uani 1 1 d . . . . .
C007 C 0.4215(2) 0.56932(6) 0.61089(10) 0.0236(3) Uani 1 1 d . . . . .
C008 C 0.6496(2) 0.50327(6) 0.73735(10) 0.0235(3) Uani 1 1 d . . . . .
C009 C 0.7612(2) 0.59498(6) 0.48208(10) 0.0242(3) Uani 1 1 d . . . . .
C00A C 0.7807(2) 0.55362(6) 0.57237(10) 0.0245(3) Uani 1 1 d . . . . .
H00A H 0.911181 0.534177 0.587939 0.029 Uiso 1 1 calc R U . . .
C00B C 0.5309(2) 0.66423(6) 0.37441(10) 0.0253(3) Uani 1 1 d . . . . .
H00B H 0.396024 0.681084 0.361684 0.030 Uiso 1 1 calc R U . . .
C00C C 0.4908(2) 0.46858(6) 0.78620(10) 0.0262(3) Uani 1 1 d . . . . .
H00C H 0.358377 0.467302 0.753744 0.031 Uiso 1 1 calc R U . . .
C00D C 0.6925(2) 0.68224(6) 0.30835(10) 0.0256(3) Uani 1 1 d . . . . .
C00E C 0.8430(2) 0.50281(7) 0.78764(10) 0.0263(3) Uani 1 1 d . . . . .
H00E H 0.954789 0.525607 0.756025 0.032 Uiso 1 1 calc R U . . .
C00F C 0.7137(2) 0.43691(6) 0.92973(10) 0.0272(3) Uani 1 1 d . . . . .
C00G C 0.8753(2) 0.47017(7) 0.88167(10) 0.0285(3) Uani 1 1 d . . . . .
H00G H 1.008179 0.470416 0.913705 0.034 Uiso 1 1 calc R U . . .
C00H C 0.5219(2) 0.43584(6) 0.88126(10) 0.0276(3) Uani 1 1 d . . . . .
H00H H 0.411108 0.412657 0.913059 0.033 Uiso 1 1 calc R U . . .
C00I C 0.9217(2) 0.61293(7) 0.41522(10) 0.0292(3) Uani 1 1 d . . . . .
H00I H 1.055901 0.595540 0.428216 0.035 Uiso 1 1 calc R U . . .
C00J C 0.8898(2) 0.65494(7) 0.33157(11) 0.0295(3) Uani 1 1 d . . . . .
H00J H 1.002406 0.666075 0.288050 0.035 Uiso 1 1 calc R U . . .
C00K C 0.8336(2) 0.75310(7) 0.16807(11) 0.0331(3) Uani 1 1 d . . . . .
H00D H 0.949883 0.759892 0.217914 0.040 Uiso 1 1 calc R U . . .
H00F H 0.791749 0.797744 0.141073 0.040 Uiso 1 1 calc R U . . .
C00L C 0.4581(2) 0.74859(7) 0.19527(11) 0.0323(3) Uani 1 1 d . . . . .
H00K H 0.355267 0.712902 0.208024 0.039 Uiso 1 1 calc R U . . .
H00L H 0.455009 0.758957 0.119372 0.039 Uiso 1 1 calc R U . . .
C00M C 0.6007(3) 0.37446(8) 1.07781(11) 0.0390(4) Uani 1 1 d . . . . .
H00M H 0.552613 0.336198 1.035815 0.058 Uiso 1 1 calc R U . . .
H00N H 0.486126 0.405640 1.088724 0.058 Uiso 1 1 calc R U . . .
H00O H 0.652451 0.358389 1.145798 0.058 Uiso 1 1 calc R U . . .
C00N C 0.9063(3) 0.71058(8) 0.07757(12) 0.0418(4) Uani 1 1 d . . . . .
H00P H 0.794148 0.705489 0.026065 0.063 Uiso 1 1 calc R U . . .
H00Q H 0.948001 0.666242 0.103580 0.063 Uiso 1 1 calc R U . . .
H00R H 1.024015 0.732461 0.044421 0.063 Uiso 1 1 calc R U . . .
C00O C 0.3975(3) 0.81119(7) 0.25597(13) 0.0406(4) Uani 1 1 d . . . . .
H00S H 0.260019 0.825863 0.233126 0.061 Uiso 1 1 calc R U . . .
H00T H 0.497315 0.847038 0.242777 0.061 Uiso 1 1 calc R U . . .
H00U H 0.396173 0.800968 0.331095 0.061 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
O001 0.0213(5) 0.0277(5) 0.0262(5) 0.0038(4) 0.0033(4) 0.0024(4)
O002 0.0236(6) 0.0388(5) 0.0355(5) 0.0087(4) 0.0070(4) 0.0036(4)
O003 0.0357(6) 0.0446(6) 0.0261(5) 0.0099(4) 0.0002(4) -0.0027(5)
N004 0.0283(7) 0.0297(6) 0.0302(6) 0.0070(5) 0.0044(5) 0.0004(5)
C005 0.0237(7) 0.0199(6) 0.0248(6) -0.0038(5) 0.0010(5) -0.0012(5)
C006 0.0227(7) 0.0224(6) 0.0241(6) -0.0037(5) 0.0040(5) -0.0017(5)
C007 0.0244(8) 0.0216(6) 0.0249(6) -0.0009(5) 0.0022(6) -0.0006(5)
C008 0.0258(7) 0.0205(6) 0.0241(6) -0.0025(5) 0.0030(6) 0.0013(5)
C009 0.0227(7) 0.0247(6) 0.0253(6) -0.0021(5) 0.0009(6) -0.0001(5)
C00A 0.0218(7) 0.0255(6) 0.0261(7) -0.0025(5) 0.0005(6) 0.0018(5)
C00B 0.0245(7) 0.0236(6) 0.0278(7) 0.0000(5) 0.0005(6) 0.0023(5)
C00C 0.0263(8) 0.0235(6) 0.0287(7) -0.0009(5) -0.0006(6) -0.0017(5)
C00D 0.0294(8) 0.0222(6) 0.0251(6) -0.0010(5) 0.0003(6) -0.0010(5)
C00E 0.0239(7) 0.0277(7) 0.0273(7) 0.0005(5) 0.0027(6) -0.0012(5)
C00F 0.0328(8) 0.0256(7) 0.0234(7) 0.0001(5) 0.0026(6) 0.0025(5)
C00G 0.0255(8) 0.0327(7) 0.0274(7) -0.0006(6) -0.0012(6) 0.0003(6)
C00H 0.0271(8) 0.0256(7) 0.0301(7) 0.0009(5) 0.0053(6) -0.0035(5)
C00I 0.0223(8) 0.0349(7) 0.0306(7) 0.0024(6) 0.0015(6) 0.0019(6)
C00J 0.0251(8) 0.0348(7) 0.0288(7) 0.0033(6) 0.0056(6) -0.0027(6)
C00K 0.0343(9) 0.0290(7) 0.0360(8) 0.0078(6) 0.0047(7) -0.0031(6)
C00L 0.0322(8) 0.0348(7) 0.0298(7) 0.0091(6) -0.0015(6) -0.0004(6)
C00M 0.0470(10) 0.0420(8) 0.0280(7) 0.0089(6) 0.0027(7) -0.0079(7)
C00N 0.0428(10) 0.0478(9) 0.0352(8) 0.0054(7) 0.0107(7) -0.0027(7)
C00O 0.0373(9) 0.0324(8) 0.0521(9) 0.0095(7) 0.0032(7) 0.0055(6)
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C006 O001 C007 123.23(10) . . ?
C00F O003 C00M 117.63(12) . . ?
C00D N004 C00K 121.46(12) . . ?
C00D N004 C00L 121.90(11) . . ?
C00L N004 C00K 115.98(11) . . ?
C007 C005 C008 119.57(12) . . ?
C00A C005 C007 117.71(12) . . ?
C00A C005 C008 122.53(13) . . ?
O001 C006 C009 119.35(11) . . ?
O001 C006 C00B 116.66(12) . . ?
C00B C006 C009 123.98(12) . . ?
O001 C007 C005 118.07(11) . . ?
O002 C007 O001 114.60(12) . . ?
O002 C007 C005 127.32(12) . . ?
C00C C008 C005 123.38(12) . . ?
C00C C008 C00E 117.05(12) . . ?
C00E C008 C005 119.57(12) . . ?
C006 C009 C00A 118.38(12) . . ?
C006 C009 C00I 115.98(12) . . ?
C00I C009 C00A 125.62(12) . . ?
C005 C00A C009 123.18(13) . . ?
C005 C00A H00A 118.4 . . ?
C009 C00A H00A 118.4 . . ?
C006 C00B H00B 120.2 . . ?
C006 C00B C00D 119.66(13) . . ?
C00D C00B H00B 120.2 . . ?
C008 C00C H00C 119.2 . . ?
C00H C00C C008 121.52(13) . . ?
C00H C00C H00C 119.2 . . ?
N004 C00D C00B 121.59(13) . . ?
N004 C00D C00J 121.20(12) . . ?
C00B C00D C00J 117.19(12) . . ?
C008 C00E H00E 119.1 . . ?
C00G C00E C008 121.76(13) . . ?
C00G C00E H00E 119.1 . . ?
O003 C00F C00G 115.30(13) . . ?
O003 C00F C00H 125.34(13) . . ?
C00H C00F C00G 119.35(12) . . ?
C00E C00G C00F 120.12(14) . . ?
C00E C00G H00G 119.9 . . ?
C00F C00G H00G 119.9 . . ?
C00C C00H H00H 119.9 . . ?
C00F C00H C00C 120.19(13) . . ?
C00F C00H H00H 119.9 . . ?
C009 C00I H00I 119.2 . . ?
C00J C00I C009 121.58(13) . . ?
C00J C00I H00I 119.2 . . ?
C00D C00J H00J 119.2 . . ?
C00I C00J C00D 121.60(13) . . ?
C00I C00J H00J 119.2 . . ?
N004 C00K H00D 108.9 . . ?
N004 C00K H00F 108.9 . . ?
N004 C00K C00N 113.33(12) . . ?
H00D C00K H00F 107.7 . . ?
C00N C00K H00D 108.9 . . ?
C00N C00K H00F 108.9 . . ?
N004 C00L H00K 109.0 . . ?
N004 C00L H00L 109.0 . . ?
N004 C00L C00O 113.14(13) . . ?
H00K C00L H00L 107.8 . . ?
C00O C00L H00K 109.0 . . ?
C00O C00L H00L 109.0 . . ?
O003 C00M H00M 109.5 . . ?
O003 C00M H00N 109.5 . . ?
O003 C00M H00O 109.5 . . ?
H00M C00M H00N 109.5 . . ?
H00M C00M H00O 109.5 . . ?
H00N C00M H00O 109.5 . . ?
C00K C00N H00P 109.5 . . ?
C00K C00N H00Q 109.5 . . ?
C00K C00N H00R 109.5 . . ?
H00P C00N H00Q 109.5 . . ?
H00P C00N H00R 109.5 . . ?
H00Q C00N H00R 109.5 . . ?
C00L C00O H00S 109.5 . . ?
C00L C00O H00T 109.5 . . ?
C00L C00O H00U 109.5 . . ?
H00S C00O H00T 109.5 . . ?
H00S C00O H00U 109.5 . . ?
H00T C00O H00U 109.5 . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O001 C006 1.3712(16) . ?
O001 C007 1.3846(16) . ?
O002 C007 1.2080(16) . ?
O003 C00F 1.3695(17) . ?
O003 C00M 1.4184(18) . ?
N004 C00D 1.3680(17) . ?
N004 C00K 1.4570(18) . ?
N004 C00L 1.4537(19) . ?
C005 C007 1.4583(19) . ?
C005 C008 1.4838(18) . ?
C005 C00A 1.3565(19) . ?
C006 C009 1.3930(19) . ?
C006 C00B 1.3745(19) . ?
C008 C00C 1.3941(19) . ?
C008 C00E 1.403(2) . ?
C009 C00A 1.4204(19) . ?
C009 C00I 1.4013(19) . ?
C00A H00A 0.9500 . ?
C00B H00B 0.9500 . ?
C00B C00D 1.4007(19) . ?
C00C H00C 0.9500 . ?
C00C C00H 1.3893(19) . ?
C00D C00J 1.419(2) . ?
C00E H00E 0.9500 . ?
C00E C00G 1.3780(19) . ?
C00F C00G 1.390(2) . ?
C00F C00H 1.383(2) . ?
C00G H00G 0.9500 . ?
C00H H00H 0.9500 . ?
C00I H00I 0.9500 . ?
C00I C00J 1.370(2) . ?
C00J H00J 0.9500 . ?
C00K H00D 0.9900 . ?
C00K H00F 0.9900 . ?
C00K C00N 1.512(2) . ?
C00L H00K 0.9900 . ?
C00L H00L 0.9900 . ?
C00L C00O 1.522(2) . ?
C00M H00M 0.9800 . ?
C00M H00N 0.9800 . ?
C00M H00O 0.9800 . ?
C00N H00P 0.9800 . ?
C00N H00Q 0.9800 . ?
C00N H00R 0.9800 . ?
C00O H00S 0.9800 . ?
C00O H00T 0.9800 . ?
C00O H00U 0.9800 . ?
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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O001 C006 C009 C00A -0.63(18) . . . . ?
O001 C006 C009 C00I -179.05(11) . . . . ?
O001 C006 C00B C00D 178.70(11) . . . . ?
O003 C00F C00G C00E -178.06(12) . . . . ?
O003 C00F C00H C00C 178.31(12) . . . . ?
N004 C00D C00J C00I -179.23(13) . . . . ?
C005 C008 C00C C00H -178.21(12) . . . . ?
C005 C008 C00E C00G 178.56(12) . . . . ?
C006 O001 C007 O002 175.62(11) . . . . ?
C006 O001 C007 C005 -3.05(17) . . . . ?
C006 C009 C00A C005 -1.67(19) . . . . ?
C006 C009 C00I C00J 0.4(2) . . . . ?
C006 C00B C00D N004 179.33(12) . . . . ?
C006 C00B C00D C00J 0.35(18) . . . . ?
C007 O001 C006 C009 3.02(17) . . . . ?
C007 O001 C006 C00B -175.81(11) . . . . ?
C007 C005 C008 C00C 28.92(18) . . . . ?
C007 C005 C008 C00E -150.21(12) . . . . ?
C007 C005 C00A C009 1.59(19) . . . . ?
C008 C005 C007 O001 175.81(10) . . . . ?
C008 C005 C007 O002 -2.7(2) . . . . ?
C008 C005 C00A C009 -173.36(12) . . . . ?
C008 C00C C00H C00F -0.18(19) . . . . ?
C008 C00E C00G C00F -0.5(2) . . . . ?
C009 C006 C00B C00D -0.07(19) . . . . ?
C009 C00I C00J C00D -0.1(2) . . . . ?
C00A C005 C007 O001 0.70(17) . . . . ?
C00A C005 C007 O002 -177.78(13) . . . . ?
C00A C005 C008 C00C -156.22(13) . . . . ?
C00A C005 C008 C00E 24.65(18) . . . . ?
C00A C009 C00I C00J -177.87(13) . . . . ?
C00B C006 C009 C00A 178.11(12) . . . . ?
C00B C006 C009 C00I -0.31(19) . . . . ?
C00B C00D C00J C00I -0.2(2) . . . . ?
C00C C008 C00E C00G -0.62(19) . . . . ?
C00D N004 C00K C00N 91.00(17) . . . . ?
C00D N004 C00L C00O 84.15(16) . . . . ?
C00E C008 C00C C00H 0.94(19) . . . . ?
C00G C00F C00H C00C -0.93(19) . . . . ?
C00H C00F C00G C00E 1.2(2) . . . . ?
C00I C009 C00A C005 176.58(13) . . . . ?
C00K N004 C00D C00B 167.43(12) . . . . ?
C00K N004 C00D C00J -13.63(19) . . . . ?
C00K N004 C00L C00O -86.59(15) . . . . ?
C00L N004 C00D C00B -2.80(19) . . . . ?
C00L N004 C00D C00J 176.13(13) . . . . ?
C00L N004 C00K C00N -98.22(15) . . . . ?
C00M O003 C00F C00G 178.80(12) . . . . ?
C00M O003 C00F C00H -0.46(19) . . . . ?