#------------------------------------------------------------------------------
#$Date: 2024-11-28 03:39:14 +0200 (Thu, 28 Nov 2024) $
#$Revision: 296144 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/57/33/1573314.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_1573314
_journal_paper_doi               10.1039/D4CP03313B
_chemical_formula_moiety         'C20 H10 N2 O S'
_chemical_formula_sum            'C20 H10 N2 O S'
_chemical_formula_weight         326.36
_chemical_name_common            R2
_chemical_name_systematic
2-((5-(dibenzo[b,d]furan-4-yl)thiophen-2-yl)methylene)malononitrile
_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             2024-04-23
_audit_creation_method
;
Olex2 1.5
(compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817)
;
_audit_update_record
;
2024-05-01 deposited with the CCDC.	2024-11-27 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 92.7345(5)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   8.54080(4)
_cell_length_b                   16.20195(11)
_cell_length_c                   22.03161(13)
_cell_measurement_reflns_used    22832
_cell_measurement_temperature    99.99(10)
_cell_measurement_theta_max      79.6740
_cell_measurement_theta_min      3.3720
_cell_volume                     3045.21(3)
_computing_cell_refinement       'CrysAlisPro 1.171.43.98a (Rigaku OD, 2023)'
_computing_data_collection
'CrysAlisPro system (CCD 43.103a 64-bit (release 20-12-2023))'
_computing_data_reduction        'CrysAlisPro 1.171.43.98a (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 2019/1 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      99.99(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    101.00 178.00   0.50    0.10    --  113.25  81.00 -41.00  154
  2  ω    101.00 172.00   0.50    0.10    --  113.25  30.00 -90.00  142
  3  ω    100.00 165.00   0.50    0.10    --  113.25  15.00-120.00  130
  4  ω    106.00 178.00   0.50    0.10    --  113.25  61.00 120.00  144
  5  ω    -27.00  12.00   0.50    0.05    --   47.72 -19.00  30.00   78
  6  ω     42.00  75.00   0.50    0.10    --  113.25 -61.00  60.00   66
  7  ω     42.00  75.00   0.50    0.10    --  113.25 -61.00  90.00   66
  8  ω     42.00  75.00   0.50    0.10    --  113.25 -61.00 -30.00   66
  9  ω     42.00  67.00   0.50    0.10    --  113.25 -61.00 -60.00   50
 10  ω     46.00  74.00   0.50    0.10    --  113.25 -61.00  30.00   56
 11  ω     49.00  75.00   0.50    0.10    --  113.25 -61.00 -90.00   52
 12  ω     42.00  75.00   0.50    0.10    --  113.25 -61.00-120.00   66
 13  ω     42.00  75.00   0.50    0.10    --  113.25 -61.00-150.00   66
 14  ω     44.00  86.00   0.50    0.10    --  113.25-125.00-150.00   84
 15  ω     50.00  86.00   0.50    0.10    --  113.25-125.00-180.00   72
 16  ω     42.00  96.00   0.50    0.10    --  113.25 -95.00-120.00  108
 17  ω     42.00 138.00   0.50    0.10    --  113.25 -81.00-164.00  192
 18  ω     57.00  83.00   0.50    0.10    --  113.25 -95.00 -90.00   52
 19  ω     62.00  93.00   0.50    0.10    --  113.25 -95.00  90.00   62
 20  ω     50.00  94.00   0.50    0.10    --  113.25 -95.00  30.00   88
 21  ω     57.00 108.00   0.50    0.10    --  113.25-125.00 -30.00  102
 22  ω    -21.00  72.00   0.50    0.05    --   47.72 -81.00-164.00  186
 23  ω    -13.00  28.00   0.50    0.05    --  -47.72  19.00 -90.00   82
 24  ω    -72.00  25.00   0.50    0.05    --  -47.72  81.00 -41.00  194
 25  ω   -116.00 -19.00   0.50    0.10    --  -91.75  81.00 -41.00  194
 26  ω    -13.00  28.00   0.50    0.05    --  -47.72  19.00-120.00   82
 27  ω    -49.00 -20.00   0.50    0.10    --  -91.75  45.00 150.00   58
 28  ω   -121.00 -35.00   0.50    0.05    --  -47.72 -38.00 120.00  172
 29  ω   -163.00 -79.00   0.50    0.10    --  -91.75 -81.00-164.00  168
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0231098000
_diffrn_orient_matrix_UB_12      0.0182347000
_diffrn_orient_matrix_UB_13      -0.0675978000
_diffrn_orient_matrix_UB_21      -0.0958270000
_diffrn_orient_matrix_UB_22      0.0800759000
_diffrn_orient_matrix_UB_23      0.0050051000
_diffrn_orient_matrix_UB_31      0.1513509000
_diffrn_orient_matrix_UB_32      0.0479341000
_diffrn_orient_matrix_UB_33      0.0174084000
_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  0.0292
_diffrn_reflns_av_unetI/netI     0.0210
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            31779
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.476
_diffrn_reflns_theta_min         3.387
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_current           '1 mA'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_diffrn_source_voltage           '50 kV'
_exptl_absorpt_coefficient_mu    1.950
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.438
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.43.98a (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            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.424
_exptl_crystal_description       block
_exptl_crystal_F_000             1344
_exptl_crystal_preparation       'Semiconducting material'
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: Chloroform'
_exptl_crystal_size_max          0.867
_exptl_crystal_size_mid          0.184
_exptl_crystal_size_min          0.112
_refine_diff_density_max         0.297
_refine_diff_density_min         -0.298
_refine_diff_density_rms         0.045
_refine_ls_extinction_coef       0.00047(8)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2019/1 (Sheldrick 2019)'
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     434
_refine_ls_number_reflns         6222
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.058
_refine_ls_R_factor_all          0.0319
_refine_ls_R_factor_gt           0.0304
_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/[σ²(Fo²)+(0.0507P)²+0.7668P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0847
_refine_ls_wR_factor_ref         0.0860
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5855
_reflns_number_total             6222
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d4cp03313b2.cif
_cod_data_source_block           sn_r2
_cod_database_code               1573314
_shelx_shelxl_version_number     2019/1
_chemical_oxdiff_formula         C20H10N2OS
_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   0.811
_shelx_estimated_absorpt_t_min   0.283
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C5(H5), C6(H6), C7(H7), C8(H8), C10(H10), C11(H11), C12(H12), C14(H14),
 C15(H15), C17(H17), C5B(H5B), C6B(H6B), C7B(H7B), C8B(H8B), C10B(H10B),
 C11B(H11B), C12B(H12B), C14B(H14B), C15B(H15B), C17B(H17B)
;
_olex2_submission_original_sample_id SNB_240423_SDc_R2
_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
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.649
_oxdiff_exptl_absorpt_empirical_full_min 0.807
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
S1 S 0.52809(3) 0.46549(2) 0.86595(2) 0.01807(9) Uani 1 1 d . . . . .
O1 O 0.79276(9) 0.34746(5) 0.70523(4) 0.01858(17) Uani 1 1 d . . . . .
N1 N 0.12996(13) 0.38034(7) 1.06832(5) 0.0314(3) Uani 1 1 d . . . . .
N2 N 0.32940(13) 0.57844(7) 0.96503(5) 0.0293(2) Uani 1 1 d . . . . .
C1 C 0.78482(12) 0.43108(7) 0.71671(5) 0.0168(2) Uani 1 1 d . . . . .
C2 C 0.86716(12) 0.47676(7) 0.67471(5) 0.0181(2) Uani 1 1 d . . . . .
C3 C 0.93064(12) 0.41662(7) 0.63386(5) 0.0184(2) Uani 1 1 d . . . . .
C4 C 0.88121(12) 0.34001(7) 0.65435(5) 0.0187(2) Uani 1 1 d . . . . .
C5 C 1.02010(13) 0.42002(8) 0.58231(5) 0.0209(2) Uani 1 1 d . . . . .
H5 H 1.055438 0.471373 0.567289 0.025 Uiso 1 1 calc R U . . .
C6 C 1.05599(13) 0.34652(8) 0.55366(5) 0.0232(2) Uani 1 1 d . . . . .
H6 H 1.116925 0.347750 0.518706 0.028 Uiso 1 1 calc R U . . .
C7 C 1.00383(14) 0.27065(8) 0.57544(5) 0.0244(2) Uani 1 1 d . . . . .
H7 H 1.030066 0.221352 0.554902 0.029 Uiso 1 1 calc R U . . .
C8 C 0.91437(14) 0.26582(8) 0.62652(5) 0.0230(2) Uani 1 1 d . . . . .
H8 H 0.878172 0.214572 0.641431 0.028 Uiso 1 1 calc R U . . .
C9 C 0.70187(12) 0.46636(7) 0.76335(5) 0.0176(2) Uani 1 1 d . . . . .
C10 C 0.70743(14) 0.55287(8) 0.76556(6) 0.0216(2) Uani 1 1 d . . . . .
H10 H 0.653862 0.580620 0.796394 0.026 Uiso 1 1 calc R U . . .
C11 C 0.78846(14) 0.59962(8) 0.72428(6) 0.0242(2) Uani 1 1 d . . . . .
H11 H 0.788322 0.658075 0.727620 0.029 Uiso 1 1 calc R U . . .
C12 C 0.86932(13) 0.56269(7) 0.67844(5) 0.0217(2) Uani 1 1 d . . . . .
H12 H 0.924475 0.594906 0.650444 0.026 Uiso 1 1 calc R U . . .
C13 C 0.61346(12) 0.41784(7) 0.80564(5) 0.0174(2) Uani 1 1 d . . . . .
C14 C 0.58167(13) 0.33417(7) 0.80482(5) 0.0205(2) Uani 1 1 d . . . . .
H14 H 0.618492 0.297520 0.775019 0.025 Uiso 1 1 calc R U . . .
C15 C 0.48987(13) 0.30897(7) 0.85228(5) 0.0212(2) Uani 1 1 d . . . . .
H15 H 0.458668 0.253367 0.858126 0.025 Uiso 1 1 calc R U . . .
C16 C 0.44884(13) 0.37317(7) 0.89000(5) 0.0191(2) Uani 1 1 d . . . . .
C17 C 0.35391(13) 0.36313(7) 0.94068(5) 0.0201(2) Uani 1 1 d . . . . .
H17 H 0.327833 0.307716 0.950033 0.024 Uiso 1 1 calc R U . . .
C18 C 0.29480(13) 0.42141(8) 0.97784(5) 0.0198(2) Uani 1 1 d . . . . .
C19 C 0.20308(14) 0.39783(8) 1.02779(5) 0.0230(2) Uani 1 1 d . . . . .
C20 C 0.31536(13) 0.50851(8) 0.97037(5) 0.0213(2) Uani 1 1 d . . . . .
S1B S 0.45224(3) 0.44129(2) 0.62515(2) 0.01739(8) Uani 1 1 d . . . . .
O1B O 0.14598(9) 0.32219(5) 0.77395(4) 0.01820(17) Uani 1 1 d . . . . .
N1B N 0.81610(12) 0.35848(6) 0.41239(5) 0.0259(2) Uani 1 1 d . . . . .
N2B N 0.68984(12) 0.55033(6) 0.53839(5) 0.0227(2) Uani 1 1 d . . . . .
C1B C 0.17658(12) 0.40537(7) 0.76908(5) 0.0171(2) Uani 1 1 d . . . . .
C2B C 0.10595(12) 0.45080(7) 0.81444(5) 0.0182(2) Uani 1 1 d . . . . .
C3B C 0.02586(12) 0.39046(7) 0.85059(5) 0.0184(2) Uani 1 1 d . . . . .
C4B C 0.05409(12) 0.31433(7) 0.82379(5) 0.0185(2) Uani 1 1 d . . . . .
C5B C -0.06359(13) 0.39336(8) 0.90199(5) 0.0212(2) Uani 1 1 d . . . . .
H5B H -0.084703 0.444408 0.921171 0.025 Uiso 1 1 calc R U . . .
C6B C -0.12103(13) 0.31949(8) 0.92440(5) 0.0238(2) Uani 1 1 d . . . . .
H6B H -0.181340 0.320267 0.959530 0.029 Uiso 1 1 calc R U . . .
C7B C -0.09144(14) 0.24416(8) 0.89607(6) 0.0245(3) Uani 1 1 d . . . . .
H7B H -0.132857 0.194756 0.912109 0.029 Uiso 1 1 calc R U . . .
C8B C -0.00245(13) 0.24023(8) 0.84482(5) 0.0224(2) Uani 1 1 d . . . . .
H8B H 0.018304 0.189345 0.825341 0.027 Uiso 1 1 calc R U . . .
C9B C 0.26651(12) 0.44087(7) 0.72441(5) 0.0176(2) Uani 1 1 d . . . . .
C10B C 0.27959(13) 0.52707(7) 0.72763(5) 0.0212(2) Uani 1 1 d . . . . .
H10B H 0.337824 0.554901 0.698180 0.025 Uiso 1 1 calc R U . . .
C11B C 0.21035(14) 0.57345(8) 0.77242(6) 0.0244(2) Uani 1 1 d . . . . .
H11B H 0.223277 0.631683 0.772833 0.029 Uiso 1 1 calc R U . . .
C12B C 0.12287(14) 0.53636(8) 0.81646(6) 0.0224(2) Uani 1 1 d . . . . .
H12B H 0.076128 0.568233 0.846942 0.027 Uiso 1 1 calc R U . . .
C13B C 0.34032(12) 0.39252(7) 0.67772(5) 0.0179(2) Uani 1 1 d . . . . .
C14B C 0.33538(14) 0.30840(7) 0.66775(5) 0.0223(2) Uani 1 1 d . . . . .
H14B H 0.280145 0.271053 0.692172 0.027 Uiso 1 1 calc R U . . .
C15B C 0.41996(14) 0.28376(7) 0.61802(5) 0.0229(2) Uani 1 1 d . . . . .
H15B H 0.426894 0.228015 0.605037 0.027 Uiso 1 1 calc R U . . .
C16B C 0.49262(13) 0.34859(7) 0.58956(5) 0.0186(2) Uani 1 1 d . . . . .
C17B C 0.58508(13) 0.33897(7) 0.53801(5) 0.0193(2) Uani 1 1 d . . . . .
H17B H 0.590262 0.284447 0.522367 0.023 Uiso 1 1 calc R U . . .
C18B C 0.66714(12) 0.39671(7) 0.50791(5) 0.0183(2) Uani 1 1 d . . . . .
C19B C 0.74983(13) 0.37472(7) 0.45502(5) 0.0203(2) Uani 1 1 d . . . . .
C20B C 0.67880(12) 0.48180(8) 0.52519(5) 0.0188(2) Uani 1 1 d . . . . .
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'
S S 0.3331 0.5567 '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
0 0 1 0.0549
0 0 -1 0.0574
1 1 1 0.2861
-1 -1 -1 0.3452
0 2 1 0.0689
0 -2 -1 0.0647
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
C13 S1 C16 91.99(5) . . ?
C1 O1 C4 105.48(8) . . ?
O1 C1 C2 111.54(10) . . ?
O1 C1 C9 124.54(10) . . ?
C9 C1 C2 123.90(11) . . ?
C1 C2 C3 105.64(10) . . ?
C12 C2 C1 119.62(10) . . ?
C12 C2 C3 134.71(11) . . ?
C4 C3 C2 105.64(10) . . ?
C4 C3 C5 118.92(11) . . ?
C5 C3 C2 135.43(11) . . ?
O1 C4 C3 111.69(10) . . ?
C8 C4 O1 124.36(10) . . ?
C8 C4 C3 123.94(11) . . ?
C3 C5 H5 120.8 . . ?
C6 C5 C3 118.42(11) . . ?
C6 C5 H5 120.8 . . ?
C5 C6 H6 119.5 . . ?
C5 C6 C7 121.08(11) . . ?
C7 C6 H6 119.5 . . ?
C6 C7 H7 119.3 . . ?
C8 C7 C6 121.48(11) . . ?
C8 C7 H7 119.3 . . ?
C4 C8 C7 116.16(11) . . ?
C4 C8 H8 121.9 . . ?
C7 C8 H8 121.9 . . ?
C1 C9 C10 114.61(10) . . ?
C1 C9 C13 123.07(10) . . ?
C10 C9 C13 122.31(10) . . ?
C9 C10 H10 118.7 . . ?
C11 C10 C9 122.52(11) . . ?
C11 C10 H10 118.7 . . ?
C10 C11 H11 119.3 . . ?
C12 C11 C10 121.43(11) . . ?
C12 C11 H11 119.3 . . ?
C2 C12 H12 121.0 . . ?
C11 C12 C2 117.91(11) . . ?
C11 C12 H12 121.0 . . ?
C9 C13 S1 120.08(9) . . ?
C14 C13 S1 110.99(8) . . ?
C14 C13 C9 128.92(10) . . ?
C13 C14 H14 123.4 . . ?
C13 C14 C15 113.18(10) . . ?
C15 C14 H14 123.4 . . ?
C14 C15 H15 123.3 . . ?
C16 C15 C14 113.33(11) . . ?
C16 C15 H15 123.3 . . ?
C15 C16 S1 110.50(9) . . ?
C15 C16 C17 123.73(11) . . ?
C17 C16 S1 125.77(9) . . ?
C16 C17 H17 115.3 . . ?
C18 C17 C16 129.41(11) . . ?
C18 C17 H17 115.3 . . ?
C17 C18 C19 120.57(11) . . ?
C17 C18 C20 124.25(10) . . ?
C20 C18 C19 115.18(10) . . ?
N1 C19 C18 178.73(14) . . ?
N2 C20 C18 178.71(13) . . ?
C13B S1B C16B 92.02(5) . . ?
C1B O1B C4B 105.57(8) . . ?
O1B C1B C2B 111.63(9) . . ?
O1B C1B C9B 124.67(10) . . ?
C9B C1B C2B 123.70(11) . . ?
C1B C2B C3B 105.52(10) . . ?
C12B C2B C1B 119.86(11) . . ?
C12B C2B C3B 134.62(11) . . ?
C4B C3B C2B 105.54(10) . . ?
C4B C3B C5B 119.06(11) . . ?
C5B C3B C2B 135.40(11) . . ?
O1B C4B C3B 111.74(10) . . ?
C8B C4B O1B 124.45(10) . . ?
C8B C4B C3B 123.81(11) . . ?
C3B C5B H5B 120.8 . . ?
C6B C5B C3B 118.30(11) . . ?
C6B C5B H5B 120.8 . . ?
C5B C6B H6B 119.4 . . ?
C5B C6B C7B 121.14(11) . . ?
C7B C6B H6B 119.4 . . ?
C6B C7B H7B 119.4 . . ?
C8B C7B C6B 121.25(11) . . ?
C8B C7B H7B 119.4 . . ?
C4B C8B C7B 116.43(11) . . ?
C4B C8B H8B 121.8 . . ?
C7B C8B H8B 121.8 . . ?
C1B C9B C10B 114.74(10) . . ?
C1B C9B C13B 122.99(10) . . ?
C10B C9B C13B 122.27(10) . . ?
C9B C10B H10B 118.8 . . ?
C11B C10B C9B 122.48(11) . . ?
C11B C10B H10B 118.8 . . ?
C10B C11B H11B 119.3 . . ?
C12B C11B C10B 121.45(11) . . ?
C12B C11B H11B 119.3 . . ?
C2B C12B H12B 121.1 . . ?
C11B C12B C2B 117.78(11) . . ?
C11B C12B H12B 121.1 . . ?
C9B C13B S1B 119.88(9) . . ?
C14B C13B S1B 111.00(8) . . ?
C14B C13B C9B 129.11(10) . . ?
C13B C14B H14B 123.4 . . ?
C13B C14B C15B 113.16(10) . . ?
C15B C14B H14B 123.4 . . ?
C14B C15B H15B 123.3 . . ?
C16B C15B C14B 113.41(11) . . ?
C16B C15B H15B 123.3 . . ?
C15B C16B S1B 110.41(8) . . ?
C15B C16B C17B 123.78(11) . . ?
C17B C16B S1B 125.81(9) . . ?
C16B C17B H17B 115.4 . . ?
C18B C17B C16B 129.23(11) . . ?
C18B C17B H17B 115.4 . . ?
C17B C18B C19B 120.64(11) . . ?
C17B C18B C20B 124.28(10) . . ?
C20B C18B C19B 115.08(10) . . ?
N1B C19B C18B 178.85(13) . . ?
N2B C20B C18B 178.94(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
S1 C13 1.7279(11) . ?
S1 C16 1.7350(12) . ?
O1 C1 1.3804(13) . ?
O1 C4 1.3866(13) . ?
N1 C19 1.1493(16) . ?
N2 C20 1.1461(17) . ?
C1 C2 1.4003(15) . ?
C1 C9 1.3979(15) . ?
C2 C3 1.4491(16) . ?
C2 C12 1.3947(16) . ?
C3 C4 1.3933(16) . ?
C3 C5 1.3997(15) . ?
C4 C8 1.3848(16) . ?
C5 H5 0.9500 . ?
C5 C6 1.3889(17) . ?
C6 H6 0.9500 . ?
C6 C7 1.4001(18) . ?
C7 H7 0.9500 . ?
C7 C8 1.3923(16) . ?
C8 H8 0.9500 . ?
C9 C10 1.4033(16) . ?
C9 C13 1.4571(15) . ?
C10 H10 0.9500 . ?
C10 C11 1.3927(17) . ?
C11 H11 0.9500 . ?
C11 C12 1.3862(17) . ?
C12 H12 0.9500 . ?
C13 C14 1.3824(16) . ?
C14 H14 0.9500 . ?
C14 C15 1.3974(16) . ?
C15 H15 0.9500 . ?
C15 C16 1.3867(17) . ?
C16 C17 1.4203(15) . ?
C17 H17 0.9500 . ?
C17 C18 1.3624(17) . ?
C18 C19 1.4328(16) . ?
C18 C20 1.4324(17) . ?
S1B C13B 1.7278(11) . ?
S1B C16B 1.7365(12) . ?
O1B C1B 1.3779(14) . ?
O1B C4B 1.3856(13) . ?
N1B C19B 1.1500(16) . ?
N2B C20B 1.1505(16) . ?
C1B C2B 1.4007(15) . ?
C1B C9B 1.4004(15) . ?
C2B C3B 1.4525(16) . ?
C2B C12B 1.3942(17) . ?
C3B C4B 1.3935(16) . ?
C3B C5B 1.3967(15) . ?
C4B C8B 1.3822(16) . ?
C5B H5B 0.9500 . ?
C5B C6B 1.3928(18) . ?
C6B H6B 0.9500 . ?
C6B C7B 1.3994(18) . ?
C7B H7B 0.9500 . ?
C7B C8B 1.3924(16) . ?
C8B H8B 0.9500 . ?
C9B C10B 1.4026(16) . ?
C9B C13B 1.4599(15) . ?
C10B H10B 0.9500 . ?
C10B C11B 1.3942(16) . ?
C11B H11B 0.9500 . ?
C11B C12B 1.3893(17) . ?
C12B H12B 0.9500 . ?
C13B C14B 1.3808(16) . ?
C14B H14B 0.9500 . ?
C14B C15B 1.3990(16) . ?
C15B H15B 0.9500 . ?
C15B C16B 1.3851(16) . ?
C16B C17B 1.4226(15) . ?
C17B H17B 0.9500 . ?
C17B C18B 1.3603(16) . ?
C18B C19B 1.4359(15) . ?
C18B C20B 1.4324(16) . ?
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
S1 C13 C14 C15 -0.08(13) . . . . ?
S1 C16 C17 C18 5.58(18) . . . . ?
O1 C1 C2 C3 0.21(12) . . . . ?
O1 C1 C2 C12 178.66(9) . . . . ?
O1 C1 C9 C10 -178.61(10) . . . . ?
O1 C1 C9 C13 0.06(17) . . . . ?
O1 C4 C8 C7 179.37(10) . . . . ?
C1 O1 C4 C3 0.65(12) . . . . ?
C1 O1 C4 C8 -178.30(11) . . . . ?
C1 C2 C3 C4 0.19(11) . . . . ?
C1 C2 C3 C5 178.72(12) . . . . ?
C1 C2 C12 C11 -0.04(16) . . . . ?
C1 C9 C10 C11 0.36(17) . . . . ?
C1 C9 C13 S1 174.46(8) . . . . ?
C1 C9 C13 C14 -7.02(18) . . . . ?
C2 C1 C9 C10 -0.34(16) . . . . ?
C2 C1 C9 C13 178.33(10) . . . . ?
C2 C3 C4 O1 -0.53(12) . . . . ?
C2 C3 C4 C8 178.43(11) . . . . ?
C2 C3 C5 C6 -178.39(12) . . . . ?
C3 C2 C12 C11 177.85(12) . . . . ?
C3 C4 C8 C7 0.54(17) . . . . ?
C3 C5 C6 C7 0.22(17) . . . . ?
C4 O1 C1 C2 -0.52(11) . . . . ?
C4 O1 C1 C9 177.93(10) . . . . ?
C4 C3 C5 C6 -0.01(16) . . . . ?
C5 C3 C4 O1 -179.35(9) . . . . ?
C5 C3 C4 C8 -0.39(17) . . . . ?
C5 C6 C7 C8 -0.06(18) . . . . ?
C6 C7 C8 C4 -0.31(17) . . . . ?
C9 C1 C2 C3 -178.26(10) . . . . ?
C9 C1 C2 C12 0.19(17) . . . . ?
C9 C10 C11 C12 -0.24(19) . . . . ?
C9 C13 C14 C15 -178.71(11) . . . . ?
C10 C9 C13 S1 -6.98(15) . . . . ?
C10 C9 C13 C14 171.55(11) . . . . ?
C10 C11 C12 C2 0.07(18) . . . . ?
C12 C2 C3 C4 -177.92(12) . . . . ?
C12 C2 C3 C5 0.6(2) . . . . ?
C13 S1 C16 C15 0.49(9) . . . . ?
C13 S1 C16 C17 -179.04(10) . . . . ?
C13 C9 C10 C11 -178.32(11) . . . . ?
C13 C14 C15 C16 0.46(15) . . . . ?
C14 C15 C16 S1 -0.62(13) . . . . ?
C14 C15 C16 C17 178.91(10) . . . . ?
C15 C16 C17 C18 -173.88(12) . . . . ?
C16 S1 C13 C9 178.54(9) . . . . ?
C16 S1 C13 C14 -0.23(9) . . . . ?
C16 C17 C18 C19 -178.73(11) . . . . ?
C16 C17 C18 C20 2.33(19) . . . . ?
S1B C13B C14B C15B -0.43(13) . . . . ?
S1B C16B C17B C18B 3.97(18) . . . . ?
O1B C1B C2B C3B 0.40(12) . . . . ?
O1B C1B C2B C12B -179.43(10) . . . . ?
O1B C1B C9B C10B 178.86(10) . . . . ?
O1B C1B C9B C13B -0.71(17) . . . . ?
O1B C4B C8B C7B 179.22(10) . . . . ?
C1B O1B C4B C3B -0.03(11) . . . . ?
C1B O1B C4B C8B -179.72(10) . . . . ?
C1B C2B C3B C4B -0.39(12) . . . . ?
C1B C2B C3B C5B 178.98(12) . . . . ?
C1B C2B C12B C11B 0.19(17) . . . . ?
C1B C9B C10B C11B 0.95(16) . . . . ?
C1B C9B C13B S1B -178.85(8) . . . . ?
C1B C9B C13B C14B 1.19(18) . . . . ?
C2B C1B C9B C10B -0.91(16) . . . . ?
C2B C1B C9B C13B 179.52(10) . . . . ?
C2B C3B C4B O1B 0.27(12) . . . . ?
C2B C3B C4B C8B 179.97(10) . . . . ?
C2B C3B C5B C6B -179.28(12) . . . . ?
C3B C2B C12B C11B -179.58(12) . . . . ?
C3B C4B C8B C7B -0.44(17) . . . . ?
C3B C5B C6B C7B -0.53(17) . . . . ?
C4B O1B C1B C2B -0.24(11) . . . . ?
C4B O1B C1B C9B 179.96(10) . . . . ?
C4B C3B C5B C6B 0.03(16) . . . . ?
C5B C3B C4B O1B -179.23(9) . . . . ?
C5B C3B C4B C8B 0.47(17) . . . . ?
C5B C6B C7B C8B 0.57(18) . . . . ?
C6B C7B C8B C4B -0.08(17) . . . . ?
C9B C1B C2B C3B -179.80(10) . . . . ?
C9B C1B C2B C12B 0.37(17) . . . . ?
C9B C10B C11B C12B -0.46(19) . . . . ?
C9B C13B C14B C15B 179.53(11) . . . . ?
C10B C9B C13B S1B 1.61(15) . . . . ?
C10B C9B C13B C14B -178.35(11) . . . . ?
C10B C11B C12B C2B -0.15(18) . . . . ?
C12B C2B C3B C4B 179.40(13) . . . . ?
C12B C2B C3B C5B -1.2(2) . . . . ?
C13B S1B C16B C15B 0.37(9) . . . . ?
C13B S1B C16B C17B 179.63(10) . . . . ?
C13B C9B C10B C11B -179.48(11) . . . . ?
C13B C14B C15B C16B 0.73(15) . . . . ?
C14B C15B C16B S1B -0.69(13) . . . . ?
C14B C15B C16B C17B -179.96(11) . . . . ?
C15B C16B C17B C18B -176.87(12) . . . . ?
C16B S1B C13B C9B -179.93(9) . . . . ?
C16B S1B C13B C14B 0.03(9) . . . . ?
C16B C17B C18B C19B -177.91(11) . . . . ?
C16B C17B C18B C20B 2.05(19) . . . . ?
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
0.0001 -0.0001 1.0007 -0.0676 0.0050 0.0174
-0.0001 0.0001 -1.0007 0.0676 -0.0050 -0.0174
0.9992 1.0009 1.0014 -0.0263 -0.0106 0.2166
-0.9992 -1.0009 -1.0014 0.0263 0.0106 -0.2166
-0.0003 2.0005 1.0004 -0.0312 0.1652 0.1133
0.0003 -2.0005 -1.0004 0.0312 -0.1652 -0.1133
