#------------------------------------------------------------------------------
#$Date: 2024-12-06 22:34:15 +0200 (Fri, 06 Dec 2024) $
#$Revision: 296666 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/16/01/7160157.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_7160157
loop_
_publ_author_name
'Bonner, Arlene'
'Baumann, Marcus'
_publ_section_title
;
Continuous flow synthesis of the antiviral drug tecovirimat and related
sp3-rich scaffolds.
;
_journal_issue 41
_journal_name_full 'Organic & biomolecular chemistry'
_journal_page_first 8323
_journal_page_last 8327
_journal_paper_doi 10.1039/d4ob01379d
_journal_volume 22
_journal_year 2024
_chemical_formula_moiety 'C11 H12 O3'
_chemical_formula_sum 'C11 H12 O3'
_chemical_formula_weight 192.21
_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 mixed
_atom_sites_solution_primary dual
_audit_creation_date 2023-11-15
_audit_creation_method
;
Olex2 1.5
(compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817)
;
_audit_update_record
;
2024-08-20 deposited with the CCDC. 2024-09-18 downloaded from the CCDC.
;
_cell_angle_alpha 90
_cell_angle_beta 94.5670(10)
_cell_angle_gamma 90
_cell_formula_units_Z 4
_cell_length_a 6.28270(10)
_cell_length_b 6.33670(10)
_cell_length_c 23.1722(3)
_cell_measurement_reflns_used 8807
_cell_measurement_temperature 104.70(14)
_cell_measurement_theta_max 76.0860
_cell_measurement_theta_min 3.8100
_cell_volume 919.59(2)
_computing_cell_refinement 'CrysAlisPro 1.171.42.92a (Rigaku OD, 2023)'
_computing_data_collection 'CrysAlisPro 1.171.42.92a (Rigaku OD, 2023)'
_computing_data_reduction 'CrysAlisPro 1.171.42.92a (Rigaku OD, 2023)'
_computing_molecular_graphics 'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material 'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement 'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution 'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_environment N~2~
_diffrn_ambient_temperature 104.70(14)
_diffrn_detector 'CCD plate'
_diffrn_detector_area_resol_mean 10.3196
_diffrn_detector_type Atlas
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):
# Type Start End Width t~exp~ \w \q \k \f Frames
#--------------------------------------------------------------------------
1 \w -99.00 -14.00 1.00 1.00 -- -41.95 142.00 -62.00 85
2 \w -114.00 -66.00 1.00 1.00 -- -41.95-142.00-119.00 48
3 \w -88.00 -7.00 1.00 1.00 -- -41.95 127.00 126.00 81
4 \w 29.00 98.00 1.00 1.00 -- 41.95-127.00 51.00 69
5 \w 87.00 172.00 1.00 1.00 -- 112.00 142.00 -62.00 85
6 \w 40.00 114.00 1.00 1.00 -- 112.00-127.00 51.00 74
7 \w 96.00 178.00 1.00 1.00 -- 112.00 127.00 126.00 82
8 \w 40.00 126.00 1.00 1.00 -- 112.00-142.00-119.00 86
9 \w -66.00 33.00 1.00 1.00 -- -41.95 37.00 30.00 99
10 \w -116.00 -18.00 1.00 1.00 -- -41.95 -37.00-150.00 98
11 \w 103.00 178.00 1.00 1.00 -- 112.00 77.00 0.00 75
12 \w 104.00 178.00 1.00 1.00 -- 112.00 111.00 90.00 74
13 \w 39.00 109.00 1.00 1.00 -- 112.00-111.00-120.00 70
14 \w 29.00 107.00 1.00 1.00 -- 112.00 -94.00 -90.00 78
15 \w 84.00 178.00 1.00 1.00 -- 112.00 30.00 -60.00 94
16 \w 39.00 109.00 1.00 1.00 -- 112.00-111.00 90.00 70
17 \w 39.00 109.00 1.00 1.00 -- 112.00-111.00 60.00 70
18 \w 104.00 178.00 1.00 1.00 -- 112.00 111.00 120.00 74
19 \w 39.00 109.00 1.00 1.00 -- 112.00-111.00 -90.00 70
20 \w 39.00 109.00 1.00 1.00 -- 112.00-111.00 30.00 70
21 \w 103.00 178.00 1.00 1.00 -- 112.00 77.00-150.00 75
22 \w -66.00 33.00 1.00 1.00 -- -41.95 37.00 -90.00 99
23 \w -115.00 -14.00 1.00 1.00 -- -41.95 -57.00 -30.00 101
24 \w -115.00 -14.00 1.00 1.00 -- -41.95 -57.00 90.00 101
25 \w 10.00 36.00 1.00 1.00 -- 41.95 75.00 119.79 26
26 \w 8.00 42.00 1.00 1.00 -- 41.95 81.00 61.31 34
27 \w 8.00 34.00 1.00 1.00 -- 41.95 83.00-145.32 26
28 \w 84.00 178.00 1.00 1.00 -- 112.00 30.00 90.00 94
29 \w 83.00 178.00 1.00 1.00 -- 112.00 59.00 -47.55 95
30 \w 83.00 178.00 1.00 1.00 -- 112.00 61.00 120.00 95
31 \w 83.00 178.00 1.00 1.00 -- 112.00 61.00-150.00 95
32 \w 104.00 178.00 1.00 1.00 -- 112.00 111.00-120.00 74
33 \w 86.00 178.00 1.00 1.00 -- 112.00 45.00 0.00 92
34 \w 83.00 178.00 1.00 1.00 -- 112.00 61.00 30.00 95
35 \w 83.00 178.00 1.00 1.00 -- 112.00 61.00-120.00 95
36 \w 83.00 118.00 1.00 1.00 -- 112.00 61.00-180.00 35
37 \w 84.00 178.00 1.00 1.00 -- 112.00 56.00 79.50 94
38 \w 84.00 178.00 1.00 1.00 -- 112.00 30.00-180.00 94
;
_diffrn_measurement_device 'four-circle diffractometer'
_diffrn_measurement_device_type 'SuperNova, Dual, Cu at home/near, Atlas'
_diffrn_measurement_method '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11 0.0475517000
_diffrn_orient_matrix_UB_12 -0.0041438000
_diffrn_orient_matrix_UB_13 -0.0642107000
_diffrn_orient_matrix_UB_21 -0.0130916000
_diffrn_orient_matrix_UB_22 -0.2427589000
_diffrn_orient_matrix_UB_23 0.0001677000
_diffrn_orient_matrix_UB_31 -0.2409287000
_diffrn_orient_matrix_UB_32 0.0123843000
_diffrn_orient_matrix_UB_33 -0.0181013000
_diffrn_radiation_monochromator mirror
_diffrn_radiation_probe x-ray
_diffrn_radiation_type 'Cu K\a'
_diffrn_radiation_wavelength 1.54184
_diffrn_reflns_av_R_equivalents 0.0336
_diffrn_reflns_av_unetI/netI 0.0143
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max 7
_diffrn_reflns_limit_h_min -7
_diffrn_reflns_limit_k_max 7
_diffrn_reflns_limit_k_min -7
_diffrn_reflns_limit_l_max 29
_diffrn_reflns_limit_l_min -29
_diffrn_reflns_number 15698
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full 67.684
_diffrn_reflns_theta_max 76.259
_diffrn_reflns_theta_min 3.827
_diffrn_source 'micro-focus sealed X-ray tube'
_diffrn_source_type 'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu 0.830
_exptl_absorpt_correction_T_max 1.000
_exptl_absorpt_correction_T_min 0.428
_exptl_absorpt_correction_type gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.42.92a (Rigaku Oxford Diffraction, 2023)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour 'translucent light colourless'
_exptl_crystal_density_diffrn 1.388
_exptl_crystal_description block
_exptl_crystal_F_000 408
_exptl_crystal_size_max 0.341
_exptl_crystal_size_mid 0.281
_exptl_crystal_size_min 0.138
_refine_diff_density_max 0.255
_refine_diff_density_min -0.219
_refine_diff_density_rms 0.039
_refine_ls_extinction_method none
_refine_ls_goodness_of_fit_ref 1.036
_refine_ls_hydrogen_treatment mixed
_refine_ls_matrix_type full
_refine_ls_number_parameters 131
_refine_ls_number_reflns 1910
_refine_ls_number_restraints 0
_refine_ls_restrained_S_all 1.036
_refine_ls_R_factor_all 0.0385
_refine_ls_R_factor_gt 0.0345
_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^)+(0.0338P)^2^+0.5281P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme calc
_refine_ls_wR_factor_gt 0.0817
_refine_ls_wR_factor_ref 0.0850
_reflns_Friedel_coverage 0.000
_reflns_number_gt 1730
_reflns_number_total 1910
_reflns_threshold_expression 'I > 2\s(I)'
_cod_data_source_file d4ob01379d2.cif
_cod_data_source_block exp_1817_AB-89-2-5F29
_cod_depositor_comments
'Adding full bibliography for 7160156--7160157.cif.'
_cod_database_code 7160157
_shelx_shelxl_version_number 2018/3
_chemical_oxdiff_formula 'C11H12O3 '
_chemical_oxdiff_usercomment AB-89-2-5F29_ArleneBonner_Baumann
_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 0.894
_shelx_estimated_absorpt_t_min 0.765
_olex2_refinement_description
;
1. Fixed Uiso
At 1.2 times of:
All C(H) groups, All C(H,H) groups
2.a Ternary CH refined with riding coordinates:
C1(H1), C3(H3), C4(H4), C5(H5), C6(H6), C7(H7), C9(H9)
2.b Secondary CH2 refined with riding coordinates:
C2(H2A,H2B)
2.c Aromatic/amide H refined with riding coordinates:
C10(H10), C11(H11)
;
_shelx_res_file
;
TITL exp_1817_auto_a.res in P2(1)/n
exp_1817_auto.res
created by SHELXL-2018/3 at 11:45:10 on 15-Nov-2023
REM Old TITL exp_1817_auto in P2(1)/n
REM SHELXT solution in P2(1)/n: R1 0.113, Rweak 0.311, Alpha 0.013
REM 0.907 for 179 systematic absences, Orientation as input
REM Formula found by SHELXT: C11 O3
CELL 1.54184 6.2827 6.3367 23.1722 90 94.567 90
ZERR 4 0.0001 0.0001 0.0003 0 0.001 0
LATT 1
SYMM 0.5-X,0.5+Y,0.5-Z
SFAC C H O
UNIT 44 48 12
L.S. 10 0 0
PLAN 5
SIZE 0.138 0.281 0.341
TEMP -168
CONF
list 4
MORE -1
fmap 2 53
BOND $H
ACTA
REM
REM
REM
WGHT 0.033800 0.528100
FVAR 0.94362
C1 1 0.175255 0.416122 0.426138 11.00000 0.02022 0.02360 =
0.02294 -0.00023 0.00548 0.00142
AFIX 13
H1 2 0.048953 0.511995 0.420288 11.00000 -1.20000
AFIX 0
C2 1 0.154914 0.227624 0.465176 11.00000 0.02417 0.02801 =
0.02560 0.00292 0.00729 -0.00197
AFIX 23
H2A 2 0.283707 0.182006 0.489358 11.00000 -1.20000
H2B 2 0.018634 0.208923 0.483271 11.00000 -1.20000
AFIX 0
C3 1 0.152944 0.196993 0.400745 11.00000 0.02048 0.02297 =
0.02483 0.00061 0.00289 -0.00266
AFIX 13
H3 2 0.012300 0.161241 0.379768 11.00000 -1.20000
AFIX 0
C4 1 0.394746 0.509275 0.415739 11.00000 0.02324 0.01922 =
0.01822 -0.00242 0.00494 -0.00079
AFIX 13
H4 2 0.416689 0.650702 0.434418 11.00000 -1.20000
AFIX 0
C5 1 0.397515 0.522697 0.348469 11.00000 0.02038 0.01750 =
0.01929 0.00058 0.00299 0.00245
AFIX 13
H5 2 0.288547 0.626007 0.332085 11.00000 -1.20000
AFIX 0
C6 1 0.357709 0.302916 0.321301 11.00000 0.01889 0.01970 =
0.01866 -0.00140 0.00089 0.00110
AFIX 13
H6 2 0.216849 0.302525 0.297938 11.00000 -1.20000
AFIX 0
C7 1 0.536884 0.275845 0.280934 11.00000 0.02156 0.02000 =
0.01849 -0.00265 0.00028 -0.00070
AFIX 13
H7 2 0.597704 0.130048 0.283848 11.00000 -1.20000
AFIX 0
C8 1 0.616656 0.582287 0.332141 11.00000 0.02475 0.01927 =
0.01591 0.00139 0.00256 0.00140
C9 1 0.353804 0.137176 0.370600 11.00000 0.02289 0.01686 =
0.02343 -0.00090 0.00317 -0.00102
AFIX 13
H9 2 0.344152 -0.009827 0.354913 11.00000 -1.20000
AFIX 0
C10 1 0.550574 0.166639 0.411445 11.00000 0.02068 0.02235 =
0.02109 0.00462 0.00362 0.00319
AFIX 43
H10 2 0.652567 0.057747 0.419495 11.00000 -1.20000
AFIX 0
C11 1 0.569976 0.357221 0.435305 11.00000 0.01952 0.02684 =
0.01682 0.00113 0.00271 -0.00188
AFIX 43
H11 2 0.685056 0.394402 0.462488 11.00000 -1.20000
AFIX 0
O1 3 0.699368 0.434054 0.299112 11.00000 0.02052 0.02309 =
0.02053 -0.00432 0.00388 -0.00102
O2 3 0.459971 0.321371 0.224511 11.00000 0.02472 0.03315 =
0.01629 -0.00306 0.00049 0.00197
O3 3 0.717893 0.740252 0.346201 11.00000 0.03164 0.02181 =
0.02546 -0.00278 0.00778 -0.00660
H2 2 0.569855 0.289911 0.200135 11.00000 0.05446
HKLF 4
REM exp_1817_auto_a.res in P2(1)/n
REM wR2 = 0.0850, GooF = S = 1.036, Restrained GooF = 1.036 for all data
REM R1 = 0.0345 for 1730 Fo > 4sig(Fo) and 0.0385 for all 1910 data
REM 131 parameters refined using 0 restraints
END
WGHT 0.0325 0.5333
REM Highest difference peak 0.255, deepest hole -0.219, 1-sigma level 0.039
Q1 1 0.3987 0.5109 0.3819 11.00000 0.05 0.25
Q2 1 0.4378 0.2855 0.3016 11.00000 0.05 0.25
Q3 1 0.2846 0.4611 0.4213 11.00000 0.05 0.25
Q4 1 0.4982 0.5559 0.3420 11.00000 0.05 0.24
Q5 1 0.6590 0.1719 0.2847 11.00000 0.05 0.24
;
_shelx_res_checksum 35035
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.871
_oxdiff_exptl_absorpt_empirical_full_min 0.645
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
C1 C 0.1753(2) 0.4161(2) 0.42614(5) 0.0221(3) Uani 1 1 d . . . . .
H1 H 0.048953 0.511995 0.420288 0.026 Uiso 1 1 calc R U . . .
C2 C 0.1549(2) 0.2276(2) 0.46518(6) 0.0256(3) Uani 1 1 d . . . . .
H2A H 0.283707 0.182006 0.489358 0.031 Uiso 1 1 calc R U . . .
H2B H 0.018634 0.208923 0.483271 0.031 Uiso 1 1 calc R U . . .
C3 C 0.1529(2) 0.1970(2) 0.40075(5) 0.0227(3) Uani 1 1 d . . . . .
H3 H 0.012300 0.161241 0.379768 0.027 Uiso 1 1 calc R U . . .
C4 C 0.39475(19) 0.5093(2) 0.41574(5) 0.0200(3) Uani 1 1 d . . . . .
H4 H 0.416689 0.650702 0.434418 0.024 Uiso 1 1 calc R U . . .
C5 C 0.39751(19) 0.52270(19) 0.34847(5) 0.0190(3) Uani 1 1 d . . . . .
H5 H 0.288547 0.626007 0.332085 0.023 Uiso 1 1 calc R U . . .
C6 C 0.35771(19) 0.30292(19) 0.32130(5) 0.0191(3) Uani 1 1 d . . . . .
H6 H 0.216849 0.302525 0.297938 0.023 Uiso 1 1 calc R U . . .
C7 C 0.53688(19) 0.2758(2) 0.28093(5) 0.0201(3) Uani 1 1 d . . . . .
H7 H 0.597704 0.130048 0.283848 0.024 Uiso 1 1 calc R U . . .
C8 C 0.6167(2) 0.58229(19) 0.33214(5) 0.0199(3) Uani 1 1 d . . . . .
C9 C 0.35380(19) 0.13718(19) 0.37060(5) 0.0210(3) Uani 1 1 d . . . . .
H9 H 0.344152 -0.009827 0.354913 0.025 Uiso 1 1 calc R U . . .
C10 C 0.55057(19) 0.1666(2) 0.41144(5) 0.0213(3) Uani 1 1 d . . . . .
H10 H 0.652567 0.057747 0.419495 0.026 Uiso 1 1 calc R U . . .
C11 C 0.56998(19) 0.3572(2) 0.43530(5) 0.0210(3) Uani 1 1 d . . . . .
H11 H 0.685056 0.394402 0.462488 0.025 Uiso 1 1 calc R U . . .
O1 O 0.69937(13) 0.43405(14) 0.29911(4) 0.0213(2) Uani 1 1 d . . . . .
O2 O 0.45997(15) 0.32137(15) 0.22451(4) 0.0248(2) Uani 1 1 d . . . . .
O3 O 0.71789(15) 0.74025(14) 0.34620(4) 0.0260(2) Uani 1 1 d . . . . .
H2 H 0.570(3) 0.290(3) 0.2001(9) 0.054(6) Uiso 1 1 d . . . . .
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
C1 0.0202(6) 0.0236(6) 0.0229(6) -0.0002(5) 0.0055(4) 0.0014(5)
C2 0.0242(6) 0.0280(7) 0.0256(6) 0.0029(5) 0.0073(5) -0.0020(5)
C3 0.0205(6) 0.0230(6) 0.0248(6) 0.0006(5) 0.0029(5) -0.0027(5)
C4 0.0232(6) 0.0192(6) 0.0182(6) -0.0024(4) 0.0049(4) -0.0008(5)
C5 0.0204(6) 0.0175(6) 0.0193(6) 0.0006(4) 0.0030(4) 0.0024(5)
C6 0.0189(6) 0.0197(6) 0.0187(5) -0.0014(4) 0.0009(4) 0.0011(5)
C7 0.0216(6) 0.0200(6) 0.0185(6) -0.0026(4) 0.0003(4) -0.0007(5)
C8 0.0247(6) 0.0193(6) 0.0159(5) 0.0014(4) 0.0026(4) 0.0014(5)
C9 0.0229(6) 0.0169(6) 0.0234(6) -0.0009(5) 0.0032(5) -0.0010(5)
C10 0.0207(6) 0.0224(6) 0.0211(6) 0.0046(5) 0.0036(5) 0.0032(5)
C11 0.0195(6) 0.0268(6) 0.0168(5) 0.0011(5) 0.0027(4) -0.0019(5)
O1 0.0205(4) 0.0231(5) 0.0205(4) -0.0043(3) 0.0039(3) -0.0010(3)
O2 0.0247(5) 0.0332(5) 0.0163(4) -0.0031(4) 0.0005(3) 0.0020(4)
O3 0.0316(5) 0.0218(5) 0.0255(5) -0.0028(4) 0.0078(4) -0.0066(4)
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'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-1 0 -1 0.1190
0 -1 -1 0.1023
0 1 1 0.1153
0 0 -15 0.0577
1 0 15 0.0842
-4 0 3 0.1301
0 0 15 0.0773
2 0 12 0.1213
4 0 2 0.1768
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
C2 C1 H1 117.2 . . ?
C2 C1 C3 59.76(8) . . ?
C2 C1 C4 121.18(11) . . ?
C3 C1 H1 117.2 . . ?
C3 C1 C4 110.41(10) . . ?
C4 C1 H1 117.2 . . ?
C1 C2 H2A 117.8 . . ?
C1 C2 H2B 117.8 . . ?
H2A C2 H2B 114.9 . . ?
C3 C2 C1 60.13(8) . . ?
C3 C2 H2A 117.8 . . ?
C3 C2 H2B 117.8 . . ?
C1 C3 H3 116.7 . . ?
C1 C3 C9 110.46(10) . . ?
C2 C3 C1 60.11(8) . . ?
C2 C3 H3 116.7 . . ?
C2 C3 C9 122.71(11) . . ?
C9 C3 H3 116.7 . . ?
C1 C4 H4 111.8 . . ?
C1 C4 C5 105.00(10) . . ?
C5 C4 H4 111.8 . . ?
C11 C4 C1 110.54(10) . . ?
C11 C4 H4 111.8 . . ?
C11 C4 C5 105.62(9) . . ?
C4 C5 H5 110.7 . . ?
C6 C5 C4 110.13(10) . . ?
C6 C5 H5 110.7 . . ?
C8 C5 C4 110.34(10) . . ?
C8 C5 H5 110.7 . . ?
C8 C5 C6 104.25(9) . . ?
C5 C6 H6 109.4 . . ?
C5 C6 C9 108.80(9) . . ?
C7 C6 C5 104.35(9) . . ?
C7 C6 H6 109.4 . . ?
C7 C6 C9 115.43(10) . . ?
C9 C6 H6 109.4 . . ?
C6 C7 H7 111.0 . . ?
O1 C7 C6 106.06(9) . . ?
O1 C7 H7 111.0 . . ?
O2 C7 C6 109.56(10) . . ?
O2 C7 H7 111.0 . . ?
O2 C7 O1 108.08(10) . . ?
O1 C8 C5 111.80(10) . . ?
O3 C8 C5 127.48(11) . . ?
O3 C8 O1 120.71(11) . . ?
C3 C9 C6 103.24(10) . . ?
C3 C9 H9 111.5 . . ?
C6 C9 H9 111.5 . . ?
C10 C9 C3 110.24(10) . . ?
C10 C9 C6 108.53(10) . . ?
C10 C9 H9 111.5 . . ?
C9 C10 H10 122.7 . . ?
C11 C10 C9 114.64(11) . . ?
C11 C10 H10 122.7 . . ?
C4 C11 H11 122.7 . . ?
C10 C11 C4 114.54(11) . . ?
C10 C11 H11 122.7 . . ?
C8 O1 C7 110.46(9) . . ?
C7 O2 H2 107.6(12) . . ?
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
C1 H1 1.0000 . ?
C1 C2 1.5099(18) . ?
C1 C3 1.5102(18) . ?
C1 C4 1.5366(16) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C2 C3 1.5046(17) . ?
C3 H3 1.0000 . ?
C3 C9 1.5377(17) . ?
C4 H4 1.0000 . ?
C4 C5 1.5626(16) . ?
C4 C11 1.5055(17) . ?
C5 H5 1.0000 . ?
C5 C6 1.5406(16) . ?
C5 C8 1.5048(17) . ?
C6 H6 1.0000 . ?
C6 C7 1.5295(16) . ?
C6 C9 1.5534(16) . ?
C7 H7 1.0000 . ?
C7 O1 1.4684(14) . ?
C7 O2 1.3876(14) . ?
C8 O1 1.3422(14) . ?
C8 O3 1.2164(15) . ?
C9 H9 1.0000 . ?
C9 C10 1.5075(17) . ?
C10 H10 0.9500 . ?
C10 C11 1.3298(18) . ?
C11 H11 0.9500 . ?
O2 H2 0.95(2) . ?
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
C1 C2 C3 C9 96.32(13) . . . . ?
C1 C3 C9 C6 -62.47(12) . . . . ?
C1 C3 C9 C10 53.30(13) . . . . ?
C1 C4 C5 C6 -57.24(12) . . . . ?
C1 C4 C5 C8 -171.79(10) . . . . ?
C1 C4 C11 C10 55.45(14) . . . . ?
C2 C1 C3 C9 -116.79(12) . . . . ?
C2 C1 C4 C5 128.54(12) . . . . ?
C2 C1 C4 C11 15.09(15) . . . . ?
C2 C3 C9 C6 -129.35(12) . . . . ?
C2 C3 C9 C10 -13.59(16) . . . . ?
C3 C1 C4 C5 62.30(12) . . . . ?
C3 C1 C4 C11 -51.16(13) . . . . ?
C3 C9 C10 C11 -53.64(14) . . . . ?
C4 C1 C2 C3 -96.84(12) . . . . ?
C4 C1 C3 C2 114.99(12) . . . . ?
C4 C1 C3 C9 -1.80(14) . . . . ?
C4 C5 C6 C7 -130.10(10) . . . . ?
C4 C5 C6 C9 -6.37(13) . . . . ?
C4 C5 C8 O1 120.15(11) . . . . ?
C4 C5 C8 O3 -58.68(16) . . . . ?
C5 C4 C11 C10 -57.61(13) . . . . ?
C5 C6 C7 O1 17.15(12) . . . . ?
C5 C6 C7 O2 -99.27(11) . . . . ?
C5 C6 C9 C3 66.34(12) . . . . ?
C5 C6 C9 C10 -50.64(12) . . . . ?
C5 C8 O1 C7 9.47(13) . . . . ?
C6 C5 C8 O1 1.94(13) . . . . ?
C6 C5 C8 O3 -176.89(12) . . . . ?
C6 C7 O1 C8 -16.96(12) . . . . ?
C6 C9 C10 C11 58.75(13) . . . . ?
C7 C6 C9 C3 -176.81(10) . . . . ?
C7 C6 C9 C10 66.22(13) . . . . ?
C8 C5 C6 C7 -11.74(12) . . . . ?
C8 C5 C6 C9 111.99(10) . . . . ?
C9 C6 C7 O1 -102.18(11) . . . . ?
C9 C6 C7 O2 141.39(10) . . . . ?
C9 C10 C11 C4 -1.59(15) . . . . ?
C11 C4 C5 C6 59.63(12) . . . . ?
C11 C4 C5 C8 -54.91(13) . . . . ?
O2 C7 O1 C8 100.46(11) . . . . ?
O3 C8 O1 C7 -171.61(11) . . . . ?
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
-0.9998 -0.0002 -1.0091 0.0173 0.0130 0.2591
0.0006 -0.9996 -0.9978 0.0682 0.2425 0.0055
-0.0006 0.9996 0.9978 -0.0682 -0.2425 -0.0055
0.0005 -0.3223 -14.9434 0.9609 0.0757 0.2664
0.5028 0.2832 14.6918 -0.9206 -0.0729 -0.3836
-4.0394 0.3320 2.8866 -0.3788 -0.0272 0.9251
-0.3722 0.3479 14.9821 -0.9812 -0.0771 -0.1772
2.3355 0.0942 11.5996 -0.6342 -0.0515 -0.7715
3.9808 -0.2226 2.0030 0.0616 0.0023 -0.9981