#------------------------------------------------------------------------------
#$Date: 2024-10-30 04:36:09 +0200 (Wed, 30 Oct 2024) $
#$Revision: 295675 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/57/29/1572975.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_1572975
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 H18 N2 O2'
_chemical_formula_sum 'C20 H18 N2 O2'
_chemical_formula_weight 318.36
_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'
_atom_sites_solution_hydrogens geom
_atom_sites_solution_primary dual
_audit_creation_date 2023-09-01
_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 99.297(6)
_cell_angle_gamma 90
_cell_formula_units_Z 4
_cell_length_a 11.4430(8)
_cell_length_b 13.2770(8)
_cell_length_c 10.8931(8)
_cell_measurement_reflns_used 6955
_cell_measurement_temperature 120
_cell_measurement_theta_max 69.96
_cell_measurement_theta_min 5.29
_cell_volume 1633.24(19)
_computing_cell_refinement
;
X-Area Recipe 1.37.0.0 (STOE, 2021)
;
_computing_data_collection
;
X-Area Pilatus3_SV 1.31.175.0 (STOE, 2021)
;
_computing_data_reduction
;
X-Area Integrate 2.5.1.0 (STOE, 2021)
X-Area LANA 2.6.2.0 (STOE, 2021)
;
_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 2.0, Darmstadt 2021
;
_computing_structure_refinement 'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution 'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature 120
_diffrn_detector Pilatus300K
_diffrn_detector_area_resol_mean 5.81
_diffrn_detector_type 'DECTRIS PILATUS 300K'
_diffrn_measured_fraction_theta_full 0.975
_diffrn_measured_fraction_theta_max 0.959
_diffrn_measurement_details '966 frames, detector distance = 60 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 0.0197
_diffrn_reflns_av_unetI/netI 0.0232
_diffrn_reflns_Laue_measured_fraction_full 0.975
_diffrn_reflns_Laue_measured_fraction_max 0.959
_diffrn_reflns_limit_h_max 9
_diffrn_reflns_limit_h_min -13
_diffrn_reflns_limit_k_max 6
_diffrn_reflns_limit_k_min -15
_diffrn_reflns_limit_l_max 12
_diffrn_reflns_limit_l_min -13
_diffrn_reflns_number 6618
_diffrn_reflns_point_group_measured_fraction_full 0.975
_diffrn_reflns_point_group_measured_fraction_max 0.959
_diffrn_reflns_theta_full 67.686
_diffrn_reflns_theta_max 69.416
_diffrn_reflns_theta_min 5.294
_diffrn_source 'GeniX 3D HF Cu'
_diffrn_source_current 0.600
_diffrn_source_power 0.030
_diffrn_source_voltage 50
_exptl_absorpt_coefficient_mu 0.677
_exptl_absorpt_correction_T_max 1.0000
_exptl_absorpt_correction_T_min 1.0000
_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 Orange
_exptl_crystal_density_diffrn 1.295
_exptl_crystal_density_method 'not measured'
_exptl_crystal_description Block
_exptl_crystal_F_000 672
_exptl_crystal_size_max 0.5
_exptl_crystal_size_mid 0.3
_exptl_crystal_size_min 0.1
_refine_diff_density_max 0.156
_refine_diff_density_min -0.242
_refine_diff_density_rms 0.045
_refine_ls_extinction_method none
_refine_ls_goodness_of_fit_ref 1.049
_refine_ls_hydrogen_treatment constr
_refine_ls_matrix_type full
_refine_ls_number_parameters 219
_refine_ls_number_reflns 2935
_refine_ls_number_restraints 0
_refine_ls_restrained_S_all 1.049
_refine_ls_R_factor_all 0.0407
_refine_ls_R_factor_gt 0.0342
_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^)+(0.0596P)^2^+0.1484P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme calc
_refine_ls_wR_factor_gt 0.0920
_refine_ls_wR_factor_ref 0.0954
_reflns_Friedel_coverage 0.000
_reflns_number_gt 2475
_reflns_number_total 2935
_reflns_threshold_expression 'I > 2\s(I)'
_cod_data_source_file d4mh01343c2.cif
_cod_data_source_block 1
_cod_original_cell_volume 1633.23(19)
_cod_database_code 1572975
_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.
;
_shelx_estimated_absorpt_t_max 0.935
_shelx_estimated_absorpt_t_min 0.728
_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:
C00L(H00B,H00F), C00M(H00G,H00J)
2.b Aromatic/amide H refined with riding coordinates:
C008(H008), C00A(H00A), C00C(H00C), C00D(H00D), C00E(H00E), C00H(H00H),
C00I(H00I), C00K(H00K)
2.c Idealised Me refined as rotating group:
C00N(H00L,H00M,H00N), C00O(H00O,H00P,H00Q)
;
_shelx_res_file
;
TITL 1_a.res in P2(1)/c
1.res
created by SHELXL-2018/3 at 12:33:25 on 01-Sep-2023
REM Old TITL
REM SHELXT solution in P2(1)/c
REM R1 0.100, Rweak 0.004, Alpha 0.018, Orientation a'=c, b'=-b, c'=a
REM Formula found by SHELXT: C20 N2 O2
CELL 1.54186 11.443 13.277 10.8931 90 99.297 90
ZERR 4 0.0008 0.0008 0.0008 0 0.006 0
LATT 1
SYMM -X,0.5+Y,0.5-Z
SFAC C H N O
UNIT 80 72 8 8
L.S. 10
PLAN 5
SIZE 0.1 0.3 0.5
TEMP -153.15
CONF
LIST 6
MORE -1
BOND $H
fmap 2
acta
REM
REM
REM
WGHT 0.059600 0.148400
FVAR 0.57071
O001 4 0.588466 0.352031 0.481199 11.00000 0.02523 0.01716 =
0.02413 0.00124 0.00471 -0.00065
O002 4 0.449751 0.234839 0.454643 11.00000 0.03051 0.01983 =
0.03734 0.00327 0.00887 -0.00367
N003 3 0.902071 0.590420 0.560142 11.00000 0.02112 0.02621 =
0.02364 0.00102 0.00182 -0.00212
N004 3 0.136223 0.736754 -0.180461 11.00000 0.02863 0.03709 =
0.02462 0.00324 0.00065 -0.00236
C005 1 0.577814 0.498021 0.347430 11.00000 0.02068 0.01820 =
0.02037 -0.00175 0.00485 0.00147
C006 1 0.636416 0.441092 0.446848 11.00000 0.02271 0.01581 =
0.02242 -0.00187 0.00927 0.00034
C007 1 0.398381 0.519620 0.177799 11.00000 0.01652 0.02047 =
0.02452 -0.00097 0.00512 -0.00253
C008 1 0.358261 0.615704 0.202599 11.00000 0.02089 0.02034 =
0.01965 -0.00266 0.00537 -0.00271
AFIX 43
H008 2 0.379937 0.644260 0.283020 11.00000 -1.20000
AFIX 0
C009 1 0.468068 0.460052 0.279480 11.00000 0.02118 0.01850 =
0.02270 -0.00331 0.00754 0.00195
C00A 1 0.287400 0.669232 0.110953 11.00000 0.02009 0.01971 =
0.02370 -0.00116 0.00673 -0.00151
AFIX 43
H00A 2 0.258079 0.733624 0.128828 11.00000 -1.20000
AFIX 0
C00B 1 0.797234 0.559652 0.491504 11.00000 0.01966 0.02230 =
0.02135 -0.00284 0.00565 0.00080
C00C 1 0.742895 0.468850 0.517206 11.00000 0.02315 0.02103 =
0.01922 0.00062 0.00402 0.00423
AFIX 43
H00C 2 0.779341 0.426663 0.582842 11.00000 -1.20000
AFIX 0
C00D 1 0.634444 0.587298 0.320396 11.00000 0.02312 0.01954 =
0.02091 0.00105 0.00476 0.00109
AFIX 43
H00D 2 0.599109 0.627661 0.252402 11.00000 -1.20000
AFIX 0
C00E 1 0.426257 0.370005 0.311656 11.00000 0.02109 0.02118 =
0.02834 -0.00290 0.00355 -0.00135
AFIX 43
H00E 2 0.356507 0.343524 0.263275 11.00000 -1.20000
AFIX 0
C00F 1 0.484003 0.313083 0.416742 11.00000 0.02250 0.01825 =
0.02802 -0.00298 0.00866 -0.00029
C00G 1 0.258804 0.628481 -0.008392 11.00000 0.01814 0.02516 =
0.02157 0.00052 0.00455 -0.00293
C00H 1 0.298271 0.532864 -0.034287 11.00000 0.02434 0.02925 =
0.02148 -0.00539 0.00408 -0.00278
AFIX 43
H00H 2 0.278168 0.505228 -0.115396 11.00000 -1.20000
AFIX 0
C00I 1 0.739642 0.617801 0.389732 11.00000 0.02368 0.02044 =
0.02330 0.00045 0.00602 -0.00240
AFIX 43
H00I 2 0.774678 0.679121 0.369208 11.00000 -1.20000
AFIX 0
C00J 1 0.190413 0.687818 -0.104768 11.00000 0.02117 0.02847 =
0.02191 -0.00331 0.00489 -0.00482
C00K 1 0.367128 0.478172 0.059045 11.00000 0.02282 0.02093 =
0.02706 -0.00527 0.00478 -0.00007
AFIX 43
H00K 2 0.393125 0.412383 0.042252 11.00000 -1.20000
AFIX 0
C00L 1 0.963048 0.529884 0.663158 11.00000 0.02011 0.02846 =
0.02744 0.00057 0.00073 0.00195
AFIX 23
H00B 2 1.048627 0.545911 0.675002 11.00000 -1.20000
H00F 2 0.953883 0.457795 0.640410 11.00000 -1.20000
AFIX 0
C00M 1 0.950593 0.689827 0.540325 11.00000 0.02333 0.02964 =
0.02858 0.00054 0.00090 -0.00602
AFIX 23
H00G 2 0.947709 0.700281 0.449900 11.00000 -1.20000
H00J 2 1.034803 0.691397 0.579815 11.00000 -1.20000
AFIX 0
C00N 1 0.918196 0.546327 0.785963 11.00000 0.02915 0.03441 =
0.02706 0.00290 0.00309 -0.00210
AFIX 137
H00L 2 0.834029 0.528704 0.776041 11.00000 -1.50000
H00M 2 0.928609 0.617190 0.810475 11.00000 -1.50000
H00N 2 0.963108 0.503662 0.850345 11.00000 -1.50000
AFIX 0
C00O 1 0.885747 0.776517 0.591975 11.00000 0.04069 0.02816 =
0.03712 -0.00276 -0.00122 -0.00323
AFIX 137
H00O 2 0.801166 0.772913 0.557972 11.00000 -1.50000
H00P 2 0.917951 0.840743 0.568268 11.00000 -1.50000
H00Q 2 0.896463 0.771587 0.682868 11.00000 -1.50000
AFIX 0
HKLF 4
REM 1_a.res in P2(1)/c
REM wR2 = 0.0954, GooF = S = 1.049, Restrained GooF = 1.049 for all data
REM R1 = 0.0342 for 2475 Fo > 4sig(Fo) and 0.0407 for all 2935 data
REM 219 parameters refined using 0 restraints
END
WGHT 0.0589 0.1348
REM Highest difference peak 0.156, deepest hole -0.242, 1-sigma level 0.045
Q1 1 0.3532 0.5579 0.2049 11.00000 0.05 0.16
Q2 1 0.3347 0.3576 0.3073 11.00000 0.05 0.14
Q3 1 0.4218 0.4366 0.3209 11.00000 0.05 0.14
Q4 1 0.3697 0.5179 0.0010 11.00000 0.05 0.14
Q5 1 0.5841 0.5536 0.3600 11.00000 0.05 0.13
;
_shelx_res_checksum 6520
_olex2_submission_special_instructions 'No special instructions were received'
_stoe_detector_distance '60.0 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 5.5
_stoe_evaluation_integration_b 0.0
_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 96.0
_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 138.9
_stoe_evaluation_lana_max_2theta_desired 138.9
_stoe_evaluation_lana_mean_redundancy 2.3
_stoe_evaluation_lana_number_refls_after_or 6618
_stoe_evaluation_lana_number_refls_outliers 691
_stoe_evaluation_lana_number_refls_total 7309
_stoe_evaluation_lana_number_refls_unique 2935
_stoe_evaluation_lana_number_refls_written 6618
_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 2/m
_stoe_evaluation_lana_table
;
#----------------------------------------------------------------------------
2Theta 17.1 31.5 45.9 60.3 74.7 89.1 103.5 117.9 132.3
#----------------------------------------------------------------------------
4.64 2.75 1.95 1.53 1.25 1.10 0.98 0.90 0.85
N(total) 62 278 470 575 1453 1328 1362 1174 607
1.9 2.3 2.1 1.8 3.1 2.5 2.3 2.1 1.6
Complet. [%%] 93.5 97.1 99.5 98.4 98.3 99.2 99.6 98.3 80.1
161.6 103.0 49.9 24.4 17.3 17.3 13.4 10.6 10.7
R(int) 0.013 0.018 0.015 0.029 0.019 0.018 0.024 0.030 0.036
#----------------------------------------------------------------------------
;
_stoe_measurement_identifier 1
_stoe_measurement_max_exposure_per_frame '0.5 s'
_stoe_measurement_mean_exposure_per_frame '0.4 s'
_stoe_measurement_min_exposure_per_frame '0.3 s'
_stoe_measurement_total_exposure_time '7 min'
_stoe_measurement_total_frame_number 966
_stoe_measurement_total_run_number 12
_stoe_measurement_tube_power '30.0 W'
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
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O001 O 0.58847(7) 0.35203(6) 0.48120(8) 0.0221(2) Uani 1 1 d . . . . .
O002 O 0.44975(8) 0.23484(6) 0.45464(9) 0.0289(2) Uani 1 1 d . . . . .
N003 N 0.90207(9) 0.59042(8) 0.56014(9) 0.0239(2) Uani 1 1 d . . . . .
N004 N 0.13622(10) 0.73675(9) -0.18046(10) 0.0305(3) Uani 1 1 d . . . . .
C005 C 0.57781(10) 0.49802(9) 0.34743(10) 0.0196(2) Uani 1 1 d . . . . .
C006 C 0.63642(10) 0.44109(8) 0.44685(11) 0.0197(2) Uani 1 1 d . . . . .
C007 C 0.39838(10) 0.51962(9) 0.17780(11) 0.0203(3) Uani 1 1 d . . . . .
C008 C 0.35826(10) 0.61570(9) 0.20260(11) 0.0201(3) Uani 1 1 d . . . . .
H008 H 0.379937 0.644260 0.283020 0.024 Uiso 1 1 calc R U . . .
C009 C 0.46807(10) 0.46005(9) 0.27948(11) 0.0204(3) Uani 1 1 d . . . . .
C00A C 0.28740(10) 0.66923(9) 0.11095(11) 0.0208(3) Uani 1 1 d . . . . .
H00A H 0.258079 0.733624 0.128828 0.025 Uiso 1 1 calc R U . . .
C00B C 0.79723(10) 0.55965(9) 0.49150(11) 0.0208(3) Uani 1 1 d . . . . .
C00C C 0.74289(10) 0.46885(9) 0.51721(11) 0.0211(3) Uani 1 1 d . . . . .
H00C H 0.779341 0.426663 0.582842 0.025 Uiso 1 1 calc R U . . .
C00D C 0.63444(10) 0.58730(9) 0.32040(11) 0.0211(3) Uani 1 1 d . . . . .
H00D H 0.599109 0.627661 0.252402 0.025 Uiso 1 1 calc R U . . .
C00E C 0.42626(11) 0.37001(9) 0.31166(12) 0.0236(3) Uani 1 1 d . . . . .
H00E H 0.356507 0.343524 0.263275 0.028 Uiso 1 1 calc R U . . .
C00F C 0.48400(11) 0.31308(9) 0.41674(12) 0.0224(3) Uani 1 1 d . . . . .
C00G C 0.25880(10) 0.62848(9) -0.00839(11) 0.0215(3) Uani 1 1 d . . . . .
C00H C 0.29827(11) 0.53286(10) -0.03429(11) 0.0250(3) Uani 1 1 d . . . . .
H00H H 0.278168 0.505228 -0.115396 0.030 Uiso 1 1 calc R U . . .
C00I C 0.73964(10) 0.61780(9) 0.38973(11) 0.0222(3) Uani 1 1 d . . . . .
H00I H 0.774678 0.679121 0.369208 0.027 Uiso 1 1 calc R U . . .
C00J C 0.19041(11) 0.68782(10) -0.10477(11) 0.0237(3) Uani 1 1 d . . . . .
C00K C 0.36713(10) 0.47817(9) 0.05905(12) 0.0235(3) Uani 1 1 d . . . . .
H00K H 0.393125 0.412383 0.042252 0.028 Uiso 1 1 calc R U . . .
C00L C 0.96305(11) 0.52988(10) 0.66316(12) 0.0257(3) Uani 1 1 d . . . . .
H00B H 1.048627 0.545911 0.675002 0.031 Uiso 1 1 calc R U . . .
H00F H 0.953883 0.457795 0.640410 0.031 Uiso 1 1 calc R U . . .
C00M C 0.95059(11) 0.68983(10) 0.54033(12) 0.0275(3) Uani 1 1 d . . . . .
H00G H 0.947709 0.700281 0.449900 0.033 Uiso 1 1 calc R U . . .
H00J H 1.034803 0.691397 0.579815 0.033 Uiso 1 1 calc R U . . .
C00N C 0.91820(12) 0.54633(11) 0.78596(12) 0.0304(3) Uani 1 1 d . . . . .
H00L H 0.834029 0.528704 0.776041 0.046 Uiso 1 1 calc R U . . .
H00M H 0.928609 0.617190 0.810475 0.046 Uiso 1 1 calc R U . . .
H00N H 0.963108 0.503662 0.850345 0.046 Uiso 1 1 calc R U . . .
C00O C 0.88575(14) 0.77652(11) 0.59198(14) 0.0362(3) Uani 1 1 d . . . . .
H00O H 0.801166 0.772913 0.557972 0.054 Uiso 1 1 calc R U . . .
H00P H 0.917951 0.840743 0.568268 0.054 Uiso 1 1 calc R U . . .
H00Q H 0.896463 0.771587 0.682868 0.054 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 0.0252(4) 0.0172(4) 0.0241(4) 0.0012(3) 0.0047(3) -0.0007(3)
O002 0.0305(5) 0.0198(5) 0.0373(5) 0.0033(4) 0.0089(4) -0.0037(4)
N003 0.0211(5) 0.0262(5) 0.0236(5) 0.0010(4) 0.0018(4) -0.0021(4)
N004 0.0286(6) 0.0371(7) 0.0246(6) 0.0032(5) 0.0006(5) -0.0024(5)
C005 0.0207(6) 0.0182(6) 0.0204(6) -0.0017(4) 0.0048(5) 0.0015(5)
C006 0.0227(6) 0.0158(5) 0.0224(6) -0.0019(4) 0.0093(5) 0.0003(4)
C007 0.0165(5) 0.0205(6) 0.0245(6) -0.0010(5) 0.0051(5) -0.0025(4)
C008 0.0209(6) 0.0203(6) 0.0196(6) -0.0027(4) 0.0054(4) -0.0027(5)
C009 0.0212(6) 0.0185(6) 0.0227(6) -0.0033(4) 0.0075(5) 0.0020(4)
C00A 0.0201(6) 0.0197(6) 0.0237(6) -0.0012(4) 0.0067(5) -0.0015(5)
C00B 0.0197(6) 0.0223(6) 0.0214(6) -0.0028(5) 0.0056(5) 0.0008(5)
C00C 0.0231(6) 0.0210(6) 0.0192(6) 0.0006(4) 0.0040(5) 0.0042(5)
C00D 0.0231(6) 0.0195(6) 0.0209(6) 0.0011(4) 0.0048(5) 0.0011(5)
C00E 0.0211(6) 0.0212(6) 0.0283(6) -0.0029(5) 0.0036(5) -0.0013(5)
C00F 0.0225(6) 0.0182(6) 0.0280(6) -0.0030(5) 0.0087(5) -0.0003(5)
C00G 0.0181(6) 0.0252(6) 0.0216(6) 0.0005(5) 0.0046(5) -0.0029(5)
C00H 0.0243(6) 0.0293(7) 0.0215(6) -0.0054(5) 0.0041(5) -0.0028(5)
C00I 0.0237(6) 0.0204(6) 0.0233(6) 0.0004(5) 0.0060(5) -0.0024(5)
C00J 0.0212(6) 0.0285(7) 0.0219(6) -0.0033(5) 0.0049(5) -0.0048(5)
C00K 0.0228(6) 0.0209(6) 0.0271(6) -0.0053(5) 0.0048(5) -0.0001(5)
C00L 0.0201(6) 0.0285(7) 0.0274(6) 0.0006(5) 0.0007(5) 0.0019(5)
C00M 0.0233(6) 0.0296(7) 0.0286(6) 0.0005(5) 0.0009(5) -0.0060(5)
C00N 0.0292(7) 0.0344(7) 0.0271(7) 0.0029(5) 0.0031(5) -0.0021(5)
C00O 0.0407(8) 0.0282(7) 0.0371(8) -0.0028(6) -0.0012(6) -0.0032(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 C00F 122.05(9) . . ?
C00B N003 C00L 121.48(10) . . ?
C00B N003 C00M 120.60(10) . . ?
C00M N003 C00L 117.65(10) . . ?
C006 C005 C009 118.50(11) . . ?
C006 C005 C00D 115.99(10) . . ?
C00D C005 C009 125.48(11) . . ?
O001 C006 C005 120.70(10) . . ?
O001 C006 C00C 115.59(10) . . ?
C00C C006 C005 123.70(11) . . ?
C008 C007 C009 119.74(10) . . ?
C008 C007 C00K 119.70(11) . . ?
C00K C007 C009 120.47(11) . . ?
C007 C008 H008 119.9 . . ?
C00A C008 C007 120.29(11) . . ?
C00A C008 H008 119.9 . . ?
C005 C009 C007 121.01(10) . . ?
C00E C009 C005 119.37(11) . . ?
C00E C009 C007 119.58(11) . . ?
C008 C00A H00A 120.1 . . ?
C008 C00A C00G 119.76(11) . . ?
C00G C00A H00A 120.1 . . ?
N003 C00B C00C 121.60(11) . . ?
N003 C00B C00I 121.22(11) . . ?
C00C C00B C00I 117.18(11) . . ?
C006 C00C C00B 119.84(11) . . ?
C006 C00C H00C 120.1 . . ?
C00B C00C H00C 120.1 . . ?
C005 C00D H00D 119.1 . . ?
C00I C00D C005 121.74(11) . . ?
C00I C00D H00D 119.1 . . ?
C009 C00E H00E 118.9 . . ?
C009 C00E C00F 122.20(11) . . ?
C00F C00E H00E 118.9 . . ?
O001 C00F C00E 117.04(10) . . ?
O002 C00F O001 116.71(11) . . ?
O002 C00F C00E 126.24(11) . . ?
C00A C00G C00J 119.01(11) . . ?
C00H C00G C00A 120.46(11) . . ?
C00H C00G C00J 120.51(11) . . ?
C00G C00H H00H 120.2 . . ?
C00K C00H C00G 119.58(11) . . ?
C00K C00H H00H 120.2 . . ?
C00B C00I H00I 119.2 . . ?
C00D C00I C00B 121.51(11) . . ?
C00D C00I H00I 119.2 . . ?
N004 C00J C00G 178.76(14) . . ?
C007 C00K H00K 119.9 . . ?
C00H C00K C007 120.16(11) . . ?
C00H C00K H00K 119.9 . . ?
N003 C00L H00B 108.7 . . ?
N003 C00L H00F 108.7 . . ?
N003 C00L C00N 114.09(10) . . ?
H00B C00L H00F 107.6 . . ?
C00N C00L H00B 108.7 . . ?
C00N C00L H00F 108.7 . . ?
N003 C00M H00G 108.7 . . ?
N003 C00M H00J 108.7 . . ?
N003 C00M C00O 114.07(11) . . ?
H00G C00M H00J 107.6 . . ?
C00O C00M H00G 108.7 . . ?
C00O C00M H00J 108.7 . . ?
C00L C00N H00L 109.5 . . ?
C00L C00N H00M 109.5 . . ?
C00L C00N H00N 109.5 . . ?
H00L C00N H00M 109.5 . . ?
H00L C00N H00N 109.5 . . ?
H00M C00N H00N 109.5 . . ?
C00M C00O H00O 109.5 . . ?
C00M C00O H00P 109.5 . . ?
C00M C00O H00Q 109.5 . . ?
H00O C00O H00P 109.5 . . ?
H00O C00O H00Q 109.5 . . ?
H00P C00O H00Q 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 1.3804(14) . ?
O001 C00F 1.3850(15) . ?
O002 C00F 1.2065(15) . ?
N003 C00B 1.3694(16) . ?
N003 C00L 1.4626(16) . ?
N003 C00M 1.4614(16) . ?
N004 C00J 1.1495(17) . ?
C005 C006 1.3997(16) . ?
C005 C009 1.4418(17) . ?
C005 C00D 1.4048(16) . ?
C006 C00C 1.3806(17) . ?
C007 C008 1.3969(16) . ?
C007 C009 1.4842(16) . ?
C007 C00K 1.3981(17) . ?
C008 H008 0.9500 . ?
C008 C00A 1.3776(17) . ?
C009 C00E 1.3547(17) . ?
C00A H00A 0.9500 . ?
C00A C00G 1.3973(17) . ?
C00B C00C 1.4053(16) . ?
C00B C00I 1.4224(17) . ?
C00C H00C 0.9500 . ?
C00D H00D 0.9500 . ?
C00D C00I 1.3747(17) . ?
C00E H00E 0.9500 . ?
C00E C00F 1.4401(17) . ?
C00G C00H 1.3915(17) . ?
C00G C00J 1.4387(17) . ?
C00H H00H 0.9500 . ?
C00H C00K 1.3867(18) . ?
C00I H00I 0.9500 . ?
C00K H00K 0.9500 . ?
C00L H00B 0.9900 . ?
C00L H00F 0.9900 . ?
C00L C00N 1.5240(18) . ?
C00M H00G 0.9900 . ?
C00M H00J 0.9900 . ?
C00M C00O 1.5254(19) . ?
C00N H00L 0.9800 . ?
C00N H00M 0.9800 . ?
C00N H00N 0.9800 . ?
C00O H00O 0.9800 . ?
C00O H00P 0.9800 . ?
C00O H00Q 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 C00C C00B -178.36(10) . . . . ?
N003 C00B C00C C006 179.17(11) . . . . ?
N003 C00B C00I C00D 179.95(11) . . . . ?
C005 C006 C00C C00B 1.03(17) . . . . ?
C005 C009 C00E C00F 3.84(17) . . . . ?
C005 C00D C00I C00B 0.83(18) . . . . ?
C006 O001 C00F O002 -179.91(10) . . . . ?
C006 O001 C00F C00E -0.34(16) . . . . ?
C006 C005 C009 C007 176.52(10) . . . . ?
C006 C005 C009 C00E -1.42(16) . . . . ?
C006 C005 C00D C00I -1.56(17) . . . . ?
C007 C008 C00A C00G -2.09(17) . . . . ?
C007 C009 C00E C00F -174.13(10) . . . . ?
C008 C007 C009 C005 -58.58(15) . . . . ?
C008 C007 C009 C00E 119.36(12) . . . . ?
C008 C007 C00K C00H 1.08(17) . . . . ?
C008 C00A C00G C00H 2.06(17) . . . . ?
C008 C00A C00G C00J -176.45(10) . . . . ?
C009 C005 C006 O001 -1.80(16) . . . . ?
C009 C005 C006 C00C 178.83(11) . . . . ?
C009 C005 C00D C00I -179.61(11) . . . . ?
C009 C007 C008 C00A -176.00(10) . . . . ?
C009 C007 C00K C00H 177.59(10) . . . . ?
C009 C00E C00F O001 -2.99(17) . . . . ?
C009 C00E C00F O002 176.53(12) . . . . ?
C00A C00G C00H C00K -0.45(17) . . . . ?
C00B N003 C00L C00N -84.05(14) . . . . ?
C00B N003 C00M C00O 74.00(15) . . . . ?
C00C C00B C00I C00D 0.87(17) . . . . ?
C00D C005 C006 O001 -179.99(10) . . . . ?
C00D C005 C006 C00C 0.64(17) . . . . ?
C00D C005 C009 C007 -5.48(17) . . . . ?
C00D C005 C009 C00E 176.58(11) . . . . ?
C00F O001 C006 C005 2.68(16) . . . . ?
C00F O001 C006 C00C -177.91(10) . . . . ?
C00G C00H C00K C007 -1.12(18) . . . . ?
C00I C00B C00C C006 -1.76(16) . . . . ?
C00J C00G C00H C00K 178.03(11) . . . . ?
C00K C007 C008 C00A 0.54(17) . . . . ?
C00K C007 C009 C005 124.91(12) . . . . ?
C00K C007 C009 C00E -57.15(15) . . . . ?
C00L N003 C00B C00C 0.40(17) . . . . ?
C00L N003 C00B C00I -178.63(11) . . . . ?
C00L N003 C00M C00O -100.15(13) . . . . ?
C00M N003 C00B C00C -173.53(11) . . . . ?
C00M N003 C00B C00I 7.44(17) . . . . ?
C00M N003 C00L C00N 90.05(13) . . . . ?