#------------------------------------------------------------------------------
#$Date: 2022-09-19 00:36:57 +0200 (Mon 19 de Sep de 2022) $
#$Revision: 277964 $
#$URL: svn://www.crystallography.net/cod/cif/7/24/55/7245502.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_7245502
loop_
_publ_author_name
'George, Gary C.'
'Unruh, Daniel K.'
'Hutchins, Kristin M.'
_publ_section_title
;
 Use of a Diels--Alder reaction to modify thermal expansion properties in
 charge-transfer cocrystals
;
_journal_name_full               CrystEngComm
_journal_paper_doi               10.1039/D2CE01207C
_journal_year                    2022
_chemical_formula_moiety         'C28 H19 Br N2 O4 S2'
_chemical_formula_sum            'C28 H19 Br N2 O4 S2'
_chemical_formula_weight         591.48
_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             2022-03-12
_audit_creation_method
;
Olex2 1.5
(compiled 2021.12.09 svn.r5202d8cf for OlexSys, GUI svn.r6439)
;
_audit_update_record
;
2022-06-17 deposited with the CCDC.	2022-09-12 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 103.198(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.6744(2)
_cell_length_b                   23.0269(3)
_cell_length_c                   8.48040(10)
_cell_measurement_reflns_used    14850
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      76.8220
_cell_measurement_theta_min      3.5630
_cell_volume                     2409.65(6)
_computing_cell_refinement       'CrysAlisPro 1.171.41.122a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.122a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.122a (Rigaku OD, 2021)'
_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      100.00(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.968
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -123.00 -34.00   0.50    0.55    --  -47.76 -20.00 -86.00  178
  2  ω    -25.00  28.00   0.50    0.55    --  -47.76  20.00  80.00  106
  3  ω    -27.00  29.00   0.50    0.55    --   47.76 -20.00 -86.00  112
  4  ω     35.00 123.00   0.50    0.55    --   47.76  20.00  80.00  176
  5  ω   -166.00 -78.00   0.50    2.19    --  -91.75 -20.00 -86.00  176
  6  ω     94.00 178.00   0.50    2.19    --  107.31  20.00  80.00  168
  7  ω   -120.00 -73.00   0.50    0.55    --  -47.76-125.00  30.00   94
  8  ω    -25.00  28.00   0.50    0.55    --  -47.76  19.00-150.00  106
  9  ω    -25.00  45.00   0.50    0.55    --   47.76 -38.00 150.00  140
 10  ω   -163.00 -86.00   0.50    2.19    --  -91.75 -99.00  30.00  154
 11  ω    -64.00 -19.00   0.50    2.19    --  -91.75  57.00  60.00   90
 12  ω    -85.00 -19.00   0.50    2.19    --  -91.75 125.00 150.00  132
 13  ω    -64.00 -19.00   0.50    2.19    --  -91.75  57.00  30.00   90
 14  ω     35.00  68.00   0.50    2.19    --  107.31 -57.00 -30.00   66
 15  ω     35.00 111.00   0.50    2.19    --  107.31-125.00-180.00  152
 16  ω     35.00  68.00   0.50    2.19    --  107.31 -57.00 -60.00   66
 17  ω     35.00 107.00   0.50    2.19    --  107.31 -77.00 -60.00  144
 18  ω     35.00  68.00   0.50    2.19    --  107.31 -57.00   0.00   66
 19  ω     35.00 106.00   0.50    2.19    --  107.31 -99.00 120.00  142
 20  ω     35.00 106.00   0.50    2.19    --  107.31 -99.00-150.00  142
 21  ω     95.00 178.00   0.50    2.19    --  107.31  19.00 120.00  166
 22  ω     35.00  68.00   0.50    2.19    --  107.31 -57.00-180.00   66
 23  ω     35.00  68.00   0.50    2.19    --  107.31 -57.00-150.00   66
 24  ω     35.00  68.00   0.50    2.19    --  107.31 -57.00  90.00   66
 25  ω   -120.00 -25.00   0.50    0.55    --  -47.76 -77.00 120.00  190
 26  ω   -120.00 -47.00   0.50    0.55    --  -47.76 -57.00 -90.00  146
 27  ω   -120.00 -25.00   0.50    0.55    --  -47.76 -77.00-150.00  190
;
_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      0.0002335000
_diffrn_orient_matrix_UB_12      0.0176434000
_diffrn_orient_matrix_UB_13      0.1753273000
_diffrn_orient_matrix_UB_21      -0.1248082000
_diffrn_orient_matrix_UB_22      -0.0008071000
_diffrn_orient_matrix_UB_23      -0.0416651000
_diffrn_orient_matrix_UB_31      0.0016946000
_diffrn_orient_matrix_UB_32      -0.0645343000
_diffrn_orient_matrix_UB_33      0.0485157000
_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  0.0638
_diffrn_reflns_av_unetI/netI     0.0387
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.968
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -28
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            26084
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.968
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.202
_diffrn_reflns_theta_min         3.582
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    4.288
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.632
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.122a (Rigaku Oxford Diffraction, 2021)
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            'clear light yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.630
_exptl_crystal_description       plate
_exptl_crystal_F_000             1200
_exptl_crystal_size_max          0.267
_exptl_crystal_size_mid          0.149
_exptl_crystal_size_min          0.039
_refine_diff_density_max         0.845
_refine_diff_density_min         -0.957
_refine_diff_density_rms         0.083
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.108
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     376
_refine_ls_number_reflns         4944
_refine_ls_number_restraints     113
_refine_ls_restrained_S_all      1.103
_refine_ls_R_factor_all          0.0681
_refine_ls_R_factor_gt           0.0624
_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)+(0.0002P)²+8.8259P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1329
_refine_ls_wR_factor_ref         0.1360
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4469
_reflns_number_total             4944
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d2ce01207c2.cif
_cod_data_source_block           DA2_BrAn_Head_to_Head_CA_Nonsolvated_auto
_cod_database_code               7245502
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C H O N S Br'
_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   0.851
_shelx_estimated_absorpt_t_min   0.394
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All C(H,H,H,H) groups
2. Restrained distances
 C19-C20A = C19-C20B
 1.519 with sigma of 0.02
 C20A-C21A = C20B-C21B
 1.30081 with sigma of 0.02
 C14-Br1 = C7-Br2
 1.81435 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
C19 \\sim C20A \\sim C20B \\sim C21B \\sim C21A: within 2A with sigma of 0.02
and sigma for terminal atoms of 0.04 within 2A
C17 \\sim C24 \\sim S2 \\sim S3: within 2A with sigma of 0.02 and sigma for
terminal atoms of 0.04 within 2A
4. Rigid body (RIGU) restrains
 C19, C20A, C20B, C21A, C21B
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
 C17, C24, S2, S3
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
5. Others
 Sof(H14)=Sof(Br2)=1-FVAR(1)
 Sof(Br1)=Sof(H7)=FVAR(1)
 Sof(H19C)=Sof(H19D)=Sof(C20B)=Sof(H20B)=Sof(C21B)=Sof(H21C)=Sof(H21D)=1-FVAR(2)
 Sof(H19A)=Sof(H19B)=Sof(C20A)=Sof(H20A)=Sof(C21A)=Sof(H21A)=Sof(H21B)=FVAR(2)
 Sof(S3)=1-FVAR(6)
 Sof(S2)=FVAR(6)
6.a Ternary CH refined with riding coordinates:
 C14(H14), C7(H7)
6.b Secondary CH2 refined with riding coordinates:
 C26(H26A,H26B), C19(H19A,H19B), C19(H19C,H19D)
6.c Aromatic/amide H refined with riding coordinates:
 C12(H12), C11(H11), C10(H10), C2(H2), C9(H9), C5(H5), C3(H3), C27(H27),
 C4(H4), C20A(H20A), C20B(H20B)
6.d X=CH2 refined with riding coordinates:
 C28(H28A,H28B), C21A(H21A,H21B), C21B(H21C,H21D)
;
_olex2_exptl_crystal_mounting_method
'Crystal was mounted on a 75 um MiTeGen cryoloop.'
_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 4.134
_oxdiff_exptl_absorpt_empirical_full_min 0.582
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
Br1 Br 0.25732(5) 0.49520(2) 0.83660(7) 0.04436(18) Uani 0.8753(19) 1 d D . P A
1
S1 S 0.35911(9) 0.36952(5) 0.96939(13) 0.0397(3) Uani 1 1 d . . . . .
S2 S 0.39399(16) 0.26821(11) 0.6931(4) 0.0456(6) Uani 0.893(13) 1 d . U P B 1
O1 O 0.6077(3) 0.38184(14) 1.1747(4) 0.0465(7) Uani 1 1 d . . . . .
O3 O 0.1138(3) 0.38352(18) 0.8605(4) 0.0583(9) Uani 1 1 d . . . . .
N1 N 0.6631(3) 0.32127(17) 0.9921(4) 0.0426(8) Uani 1 1 d . . . . .
N2 N 0.1196(3) 0.31859(18) 0.6582(5) 0.0525(10) Uani 1 1 d . . . . .
O4 O 0.1705(3) 0.26084(17) 0.4694(5) 0.0714(11) Uani 1 1 d . . . . .
O2 O 0.6547(3) 0.25518(17) 0.7849(5) 0.0681(11) Uani 1 1 d . . . . .
C13 C 0.4062(3) 0.44085(18) 0.6689(5) 0.0377(9) Uani 1 1 d . . . . .
C23 C 0.4800(4) 0.34039(19) 0.9447(5) 0.0395(9) Uani 1 1 d . . . . .
C16 C 0.2791(3) 0.37385(18) 0.7581(5) 0.0384(9) Uani 1 1 d . . . . .
C14 C 0.2903(4) 0.43770(19) 0.6918(5) 0.0406(10) Uani 1 1 d D . . . .
H14 H 0.275969 0.468072 0.768611 0.049 Uiso 0.1247(19) 1 calc R U P A 2
C22 C 0.5879(4) 0.35283(19) 1.0552(5) 0.0402(10) Uani 1 1 d . . . . .
C24 C 0.4947(4) 0.30220(19) 0.8351(6) 0.0447(10) Uani 1 1 d . U . . .
C17 C 0.2987(4) 0.3297(2) 0.6297(5) 0.0453(10) Uani 1 1 d . U . . .
C12 C 0.4875(4) 0.4780(2) 0.7440(6) 0.0458(11) Uani 1 1 d . . . . .
H12 H 0.474541 0.505227 0.821491 0.055 Uiso 1 1 calc R U . . .
C8 C 0.4256(4) 0.3999(2) 0.5566(5) 0.0429(10) Uani 1 1 d . . . . .
C1 C 0.2139(4) 0.4434(2) 0.5250(6) 0.0454(11) Uani 1 1 d . . . . .
C26 C 0.7757(4) 0.3125(2) 1.0757(6) 0.0514(12) Uani 1 1 d . . . . .
H26A H 0.797095 0.272509 1.054016 0.062 Uiso 1 1 calc R U . . .
H26B H 0.781363 0.315941 1.193713 0.062 Uiso 1 1 calc R U . . .
C15 C 0.1619(4) 0.3609(2) 0.7705(6) 0.0475(11) Uani 1 1 d . . . . .
C11 C 0.5884(4) 0.4755(2) 0.7063(6) 0.0545(13) Uani 1 1 d . . . . .
H11 H 0.644106 0.501561 0.756685 0.065 Uiso 1 1 calc R U . . .
C18 C 0.1911(4) 0.2980(2) 0.5744(6) 0.0529(12) Uani 1 1 d . . . . .
C25 C 0.6120(4) 0.2888(2) 0.8607(6) 0.0479(11) Uani 1 1 d . . . . .
C6 C 0.2362(4) 0.4024(2) 0.4151(6) 0.0486(11) Uani 1 1 d . . . . .
C7 C 0.3291(4) 0.3627(2) 0.4862(5) 0.0494(11) Uani 1 1 d D . . . .
H7 H 0.344852 0.335244 0.403155 0.059 Uiso 0.8753(19) 1 calc R U P A 1
C10 C 0.6078(4) 0.4352(3) 0.5950(7) 0.0580(14) Uani 1 1 d . . . . .
H10 H 0.676815 0.433722 0.568966 0.070 Uiso 1 1 calc R U . . .
C2 C 0.1330(4) 0.4843(3) 0.4742(7) 0.0566(13) Uani 1 1 d . . . . .
H2 H 0.116589 0.512113 0.547822 0.068 Uiso 1 1 calc R U . . .
C9 C 0.5268(4) 0.3967(2) 0.5214(6) 0.0528(12) Uani 1 1 d . . . . .
H9 H 0.540898 0.368395 0.447308 0.063 Uiso 1 1 calc R U . . .
C5 C 0.1764(4) 0.4018(3) 0.2561(6) 0.0599(14) Uani 1 1 d . . . . .
H5 H 0.190386 0.373051 0.183079 0.072 Uiso 1 1 calc R U . . .
C3 C 0.0756(4) 0.4836(3) 0.3113(7) 0.0632(16) Uani 1 1 d . . . . .
H3 H 0.020893 0.511835 0.274290 0.076 Uiso 1 1 calc R U . . .
C27 C 0.8528(4) 0.3534(3) 1.0295(7) 0.0604(14) Uani 1 1 d . . . . .
H27 H 0.927246 0.348289 1.079849 0.072 Uiso 1 1 calc R U . . .
C4 C 0.0973(4) 0.4424(3) 0.2040(7) 0.0649(16) Uani 1 1 d . . . . .
H4 H 0.057517 0.442424 0.094581 0.078 Uiso 1 1 calc R U . . .
C19 C 0.0086(4) 0.2968(3) 0.6393(8) 0.0668(15) Uani 1 1 d D U . . .
H19A H -0.016083 0.302436 0.740904 0.080 Uiso 0.657(11) 1 calc R U P C 1
H19B H 0.005705 0.254764 0.613656 0.080 Uiso 0.657(11) 1 calc R U P C 1
H19C H -0.001464 0.287501 0.748955 0.080 Uiso 0.343(11) 1 calc R U P C 2
H19D H 0.003809 0.259606 0.579356 0.080 Uiso 0.343(11) 1 calc R U P C 2
C28 C 0.8291(5) 0.3954(3) 0.9275(8) 0.081(2) Uani 1 1 d . . . . .
H28A H 0.755747 0.402296 0.873971 0.097 Uiso 1 1 calc R U . . .
H28B H 0.884883 0.419520 0.905695 0.097 Uiso 1 1 calc R U . . .
Br2 Br 0.3365(6) 0.3145(2) 0.3351(6) 0.076(2) Uani 0.1247(19) 1 d D . P A 2
C20A C -0.0636(7) 0.3306(5) 0.5016(11) 0.055(2) Uani 0.657(11) 1 d D U P C 1
H20A H -0.040106 0.336733 0.404223 0.066 Uiso 0.657(11) 1 calc R U P C 1
C21A C -0.1578(6) 0.3516(4) 0.5145(11) 0.059(2) Uani 0.657(11) 1 d D U P C 1
H21A H -0.182170 0.345714 0.611258 0.071 Uiso 0.657(11) 1 calc R U P C 1
H21B H -0.201530 0.372542 0.427037 0.071 Uiso 0.657(11) 1 calc R U P C 1
C20B C -0.0868(16) 0.3337(9) 0.556(3) 0.068(4) Uani 0.343(11) 1 d D U P C 2
H20B H -0.155372 0.326768 0.580117 0.082 Uiso 0.343(11) 1 calc R U P C 2
C21B C -0.0787(14) 0.3740(7) 0.4547(19) 0.060(4) Uani 0.343(11) 1 d D U P C 2
H21C H -0.010845 0.381620 0.429217 0.072 Uiso 0.343(11) 1 calc R U P C 2
H21D H -0.140638 0.396193 0.405276 0.072 Uiso 0.343(11) 1 calc R U P C 2
S3 S 0.4111(17) 0.2826(11) 0.635(4) 0.047(5) Uani 0.107(13) 1 d . U P B 2
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'
Br Br -0.6763 1.2805 '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
-1 -13 3 0.1274
2 -5 -5 0.0694
2 0 -5 0.0894
-2 12 3 0.0524
-8 -1 0 0.0299
8 1 0 0.0094
7 -7 1 0.0645
8 5 -2 0.0602
-8 -3 2 0.0681
-5 -11 1 0.0982
-2 -13 -2 0.0979
3 -7 -5 0.0658
7 -5 -3 0.0458
7 3 -4 0.0670
2 -6 4 0.1066
3 10 3 0.0411
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
C23 S1 C16 102.0(2) . . ?
C24 S2 C17 100.6(2) . . ?
C22 N1 C26 124.3(4) . . ?
C25 N1 C22 110.9(4) . . ?
C25 N1 C26 123.2(4) . . ?
C15 N2 C19 121.9(5) . . ?
C18 N2 C15 114.0(4) . . ?
C18 N2 C19 124.1(5) . . ?
C12 C13 C14 127.6(4) . . ?
C12 C13 C8 120.2(4) . . ?
C8 C13 C14 112.2(4) . . ?
C22 C23 S1 123.9(3) . . ?
C24 C23 S1 127.8(4) . . ?
C24 C23 C22 108.2(4) . . ?
C14 C16 S1 108.6(3) . . ?
C17 C16 S1 120.3(3) . . ?
C17 C16 C14 108.5(3) . . ?
C15 C16 S1 104.3(3) . . ?
C15 C16 C14 111.5(4) . . ?
C15 C16 C17 103.5(4) . . ?
C13 C14 Br1 113.9(3) . . ?
C13 C14 C16 104.7(3) . . ?
C13 C14 H14 111.9 . . ?
C16 C14 Br1 111.2(3) . . ?
C16 C14 H14 111.9 . . ?
C1 C14 Br1 110.5(3) . . ?
C1 C14 C13 107.6(4) . . ?
C1 C14 C16 108.6(4) . . ?
C1 C14 H14 111.9 . . ?
O1 C22 N1 126.0(4) . . ?
O1 C22 C23 128.6(4) . . ?
N1 C22 C23 105.4(4) . . ?
C23 C24 S2 126.2(4) . . ?
C23 C24 C25 109.4(4) . . ?
C23 C24 S3 131.9(6) . . ?
C25 C24 S2 124.3(4) . . ?
C25 C24 S3 115.5(8) . . ?
C16 C17 S2 119.6(3) . . ?
C16 C17 C7 109.6(4) . . ?
C16 C17 S3 129.5(7) . . ?
C18 C17 S2 101.6(3) . . ?
C18 C17 C16 104.7(4) . . ?
C18 C17 C7 110.9(4) . . ?
C18 C17 S3 111.8(8) . . ?
C7 C17 S2 109.8(4) . . ?
C7 C17 S3 88.8(14) . . ?
C13 C12 H12 120.0 . . ?
C13 C12 C11 120.0(5) . . ?
C11 C12 H12 120.0 . . ?
C13 C8 C7 113.7(4) . . ?
C9 C8 C13 119.8(5) . . ?
C9 C8 C7 126.5(5) . . ?
C6 C1 C14 112.2(4) . . ?
C2 C1 C14 127.9(5) . . ?
C2 C1 C6 119.9(5) . . ?
N1 C26 H26A 108.6 . . ?
N1 C26 H26B 108.6 . . ?
N1 C26 C27 114.8(4) . . ?
H26A C26 H26B 107.6 . . ?
C27 C26 H26A 108.6 . . ?
C27 C26 H26B 108.6 . . ?
O3 C15 N2 124.8(5) . . ?
O3 C15 C16 126.7(5) . . ?
N2 C15 C16 108.5(4) . . ?
C12 C11 H11 120.0 . . ?
C10 C11 C12 120.0(5) . . ?
C10 C11 H11 120.0 . . ?
N2 C18 C17 109.2(4) . . ?
O4 C18 N2 124.7(5) . . ?
O4 C18 C17 126.1(5) . . ?
N1 C25 C24 106.1(4) . . ?
O2 C25 N1 126.4(5) . . ?
O2 C25 C24 127.5(5) . . ?
C1 C6 C7 113.7(4) . . ?
C5 C6 C1 120.4(5) . . ?
C5 C6 C7 126.0(5) . . ?
C17 C7 H7 111.5 . . ?
C17 C7 Br2 109.5(4) . . ?
C8 C7 C17 107.0(4) . . ?
C8 C7 C6 107.8(4) . . ?
C8 C7 H7 111.5 . . ?
C8 C7 Br2 119.3(4) . . ?
C6 C7 C17 107.4(4) . . ?
C6 C7 H7 111.5 . . ?
C6 C7 Br2 105.4(4) . . ?
C11 C10 H10 119.8 . . ?
C11 C10 C9 120.3(5) . . ?
C9 C10 H10 119.8 . . ?
C1 C2 H2 120.7 . . ?
C1 C2 C3 118.5(6) . . ?
C3 C2 H2 120.7 . . ?
C8 C9 C10 119.7(5) . . ?
C8 C9 H9 120.2 . . ?
C10 C9 H9 120.2 . . ?
C6 C5 H5 119.9 . . ?
C4 C5 C6 120.2(6) . . ?
C4 C5 H5 119.9 . . ?
C2 C3 H3 119.4 . . ?
C4 C3 C2 121.1(5) . . ?
C4 C3 H3 119.4 . . ?
C26 C27 H27 116.9 . . ?
C28 C27 C26 126.3(5) . . ?
C28 C27 H27 116.9 . . ?
C5 C4 C3 119.8(5) . . ?
C5 C4 H4 120.1 . . ?
C3 C4 H4 120.1 . . ?
N2 C19 H19A 110.2 . . ?
N2 C19 H19B 110.2 . . ?
N2 C19 H19C 107.3 . . ?
N2 C19 H19D 107.3 . . ?
N2 C19 C20A 107.5(6) . . ?
N2 C19 C20B 120.1(9) . . ?
H19A C19 H19B 108.5 . . ?
H19C C19 H19D 106.9 . . ?
C20A C19 H19A 110.2 . . ?
C20A C19 H19B 110.2 . . ?
C20B C19 H19C 107.3 . . ?
C20B C19 H19D 107.3 . . ?
C27 C28 H28A 120.0 . . ?
C27 C28 H28B 120.0 . . ?
H28A C28 H28B 120.0 . . ?
C19 C20A H20A 119.3 . . ?
C21A C20A C19 121.4(8) . . ?
C21A C20A H20A 119.3 . . ?
C20A C21A H21A 120.0 . . ?
C20A C21A H21B 120.0 . . ?
H21A C21A H21B 120.0 . . ?
C19 C20B H20B 118.7 . . ?
C21B C20B C19 122.7(18) . . ?
C21B C20B H20B 118.7 . . ?
C20B C21B H21C 120.0 . . ?
C20B C21B H21D 120.0 . . ?
H21C C21B H21D 120.0 . . ?
C17 S3 C24 99.4(9) . . ?
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
Br1 C14 1.915(4) . ?
S1 C23 1.729(5) . ?
S1 C16 1.849(4) . ?
S2 C24 1.729(5) . ?
S2 C17 1.858(5) . ?
O1 C22 1.192(5) . ?
O3 C15 1.198(6) . ?
N1 C22 1.398(6) . ?
N1 C26 1.455(6) . ?
N1 C25 1.375(6) . ?
N2 C15 1.382(6) . ?
N2 C18 1.359(7) . ?
N2 C19 1.467(6) . ?
O4 C18 1.219(6) . ?
O2 C25 1.211(6) . ?
C13 C14 1.527(6) . ?
C13 C12 1.378(6) . ?
C13 C8 1.401(6) . ?
C23 C22 1.499(6) . ?
C23 C24 1.323(6) . ?
C16 C14 1.592(6) . ?
C16 C17 1.551(6) . ?
C16 C15 1.542(6) . ?
C14 H14 1.0000 . ?
C14 C1 1.527(6) . ?
C24 C25 1.484(7) . ?
C24 S3 1.838(18) . ?
C17 C18 1.523(7) . ?
C17 C7 1.557(7) . ?
C17 S3 1.782(15) . ?
C12 H12 0.9500 . ?
C12 C11 1.388(7) . ?
C8 C7 1.500(7) . ?
C8 C9 1.384(6) . ?
C1 C6 1.400(7) . ?
C1 C2 1.386(7) . ?
C26 H26A 0.9900 . ?
C26 H26B 0.9900 . ?
C26 C27 1.474(7) . ?
C11 H11 0.9500 . ?
C11 C10 1.386(8) . ?
C6 C7 1.504(7) . ?
C6 C5 1.388(7) . ?
C7 H7 1.0000 . ?
C7 Br2 1.713(6) . ?
C10 H10 0.9500 . ?
C10 C9 1.391(8) . ?
C2 H2 0.9500 . ?
C2 C3 1.407(7) . ?
C9 H9 0.9500 . ?
C5 H5 0.9500 . ?
C5 C4 1.369(8) . ?
C3 H3 0.9500 . ?
C3 C4 1.384(9) . ?
C27 H27 0.9500 . ?
C27 C28 1.286(8) . ?
C4 H4 0.9500 . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
C19 H19C 0.9900 . ?
C19 H19D 0.9900 . ?
C19 C20A 1.524(10) . ?
C19 C20B 1.514(17) . ?
C28 H28A 0.9500 . ?
C28 H28B 0.9500 . ?
C20A H20A 0.9500 . ?
C20A C21A 1.315(11) . ?
C21A H21A 0.9500 . ?
C21A H21B 0.9500 . ?
C20B H20B 0.9500 . ?
C20B C21B 1.286(19) . ?
C21B H21C 0.9500 . ?
C21B H21D 0.9500 . ?
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
Br1 C14 C1 C6 179.4(3) . . . . ?
Br1 C14 C1 C2 2.1(6) . . . . ?
S1 C23 C22 O1 2.3(7) . . . . ?
S1 C23 C22 N1 -179.7(3) . . . . ?
S1 C23 C24 S2 -3.8(7) . . . . ?
S1 C23 C24 C25 -179.1(3) . . . . ?
S1 C23 C24 S3 22.7(19) . . . . ?
S1 C16 C14 Br1 -51.7(3) . . . . ?
S1 C16 C14 C13 71.8(4) . . . . ?
S1 C16 C14 C1 -173.4(3) . . . . ?
S1 C16 C17 S2 5.6(5) . . . . ?
S1 C16 C17 C18 118.5(4) . . . . ?
S1 C16 C17 C7 -122.4(4) . . . . ?
S1 C16 C17 S3 -17.0(18) . . . . ?
S1 C16 C15 O3 50.4(6) . . . . ?
S1 C16 C15 N2 -130.1(3) . . . . ?
S2 C24 C25 N1 -174.9(4) . . . . ?
S2 C24 C25 O2 3.3(8) . . . . ?
S2 C17 C18 N2 123.9(4) . . . . ?
S2 C17 C18 O4 -57.6(6) . . . . ?
S2 C17 C7 C8 -77.4(4) . . . . ?
S2 C17 C7 C6 167.1(3) . . . . ?
N1 C26 C27 C28 1.5(9) . . . . ?
N2 C19 C20A C21A -134.8(9) . . . . ?
N2 C19 C20B C21B 24(3) . . . . ?
C13 C14 C1 C6 54.5(5) . . . . ?
C13 C14 C1 C2 -122.8(5) . . . . ?
C13 C12 C11 C10 -1.0(7) . . . . ?
C13 C8 C7 C17 -60.4(5) . . . . ?
C13 C8 C7 C6 54.9(5) . . . . ?
C13 C8 C7 Br2 174.8(4) . . . . ?
C13 C8 C9 C10 -1.5(7) . . . . ?
C23 S1 C16 C14 -96.0(3) . . . . ?
C23 S1 C16 C17 29.7(4) . . . . ?
C23 S1 C16 C15 145.0(3) . . . . ?
C23 C24 C25 N1 0.5(5) . . . . ?
C23 C24 C25 O2 178.8(5) . . . . ?
C23 C24 S3 C17 -1(3) . . . . ?
C16 S1 C23 C22 149.5(4) . . . . ?
C16 S1 C23 C24 -34.2(5) . . . . ?
C16 C14 C1 C6 -58.4(5) . . . . ?
C16 C14 C1 C2 124.3(5) . . . . ?
C16 C17 C18 N2 -1.3(5) . . . . ?
C16 C17 C18 O4 177.2(5) . . . . ?
C16 C17 C7 C8 55.9(5) . . . . ?
C16 C17 C7 C6 -59.6(5) . . . . ?
C16 C17 C7 Br2 -173.6(4) . . . . ?
C16 C17 S3 C24 0(3) . . . . ?
C14 C13 C12 C11 -178.8(4) . . . . ?
C14 C13 C8 C7 -0.2(5) . . . . ?
C14 C13 C8 C9 -179.9(4) . . . . ?
C14 C16 C17 S2 131.3(4) . . . . ?
C14 C16 C17 C18 -115.8(4) . . . . ?
C14 C16 C17 C7 3.3(5) . . . . ?
C14 C16 C17 S3 108.7(17) . . . . ?
C14 C16 C15 O3 -66.6(6) . . . . ?
C14 C16 C15 N2 112.9(4) . . . . ?
C14 C1 C6 C7 0.0(6) . . . . ?
C14 C1 C6 C5 -178.6(4) . . . . ?
C14 C1 C2 C3 176.6(4) . . . . ?
C22 N1 C26 C27 -96.5(6) . . . . ?
C22 N1 C25 O2 -176.5(5) . . . . ?
C22 N1 C25 C24 1.7(5) . . . . ?
C22 C23 C24 S2 173.0(4) . . . . ?
C22 C23 C24 C25 -2.4(5) . . . . ?
C22 C23 C24 S3 -160.5(18) . . . . ?
C24 S2 C17 C16 -38.8(5) . . . . ?
C24 S2 C17 C18 -153.4(4) . . . . ?
C24 S2 C17 C7 89.1(4) . . . . ?
C24 C23 C22 O1 -174.7(5) . . . . ?
C24 C23 C22 N1 3.4(5) . . . . ?
C17 S2 C24 C23 41.1(5) . . . . ?
C17 S2 C24 C25 -144.2(4) . . . . ?
C17 C16 C14 Br1 176.0(3) . . . . ?
C17 C16 C14 C13 -60.5(4) . . . . ?
C17 C16 C14 C1 54.2(5) . . . . ?
C17 C16 C15 O3 177.0(5) . . . . ?
C17 C16 C15 N2 -3.5(5) . . . . ?
C12 C13 C14 Br1 2.7(6) . . . . ?
C12 C13 C14 C16 -119.1(5) . . . . ?
C12 C13 C14 C1 125.5(5) . . . . ?
C12 C13 C8 C7 179.8(4) . . . . ?
C12 C13 C8 C9 0.1(6) . . . . ?
C12 C11 C10 C9 -0.4(7) . . . . ?
C8 C13 C14 Br1 -177.2(3) . . . . ?
C8 C13 C14 C16 61.0(4) . . . . ?
C8 C13 C14 C1 -54.4(5) . . . . ?
C8 C13 C12 C11 1.1(6) . . . . ?
C1 C6 C7 C17 60.2(5) . . . . ?
C1 C6 C7 C8 -54.8(5) . . . . ?
C1 C6 C7 Br2 176.9(4) . . . . ?
C1 C6 C5 C4 2.0(8) . . . . ?
C1 C2 C3 C4 1.3(8) . . . . ?
C26 N1 C22 O1 9.0(7) . . . . ?
C26 N1 C22 C23 -169.1(4) . . . . ?
C26 N1 C25 O2 -10.3(8) . . . . ?
C26 N1 C25 C24 167.9(4) . . . . ?
C15 N2 C18 O4 -179.6(5) . . . . ?
C15 N2 C18 C17 -1.0(6) . . . . ?
C15 N2 C19 C20A 95.6(7) . . . . ?
C15 N2 C19 C20B 74.4(13) . . . . ?
C15 C16 C14 Br1 62.7(4) . . . . ?
C15 C16 C14 C13 -173.8(4) . . . . ?
C15 C16 C14 C1 -59.1(5) . . . . ?
C15 C16 C17 S2 -110.1(4) . . . . ?
C15 C16 C17 C18 2.8(4) . . . . ?
C15 C16 C17 C7 121.9(4) . . . . ?
C15 C16 C17 S3 -132.7(17) . . . . ?
C11 C10 C9 C8 1.6(7) . . . . ?
C18 N2 C15 O3 -177.5(5) . . . . ?
C18 N2 C15 C16 2.9(5) . . . . ?
C18 N2 C19 C20A -87.4(7) . . . . ?
C18 N2 C19 C20B -108.6(13) . . . . ?
C18 C17 C7 C8 171.1(4) . . . . ?
C18 C17 C7 C6 55.6(5) . . . . ?
C18 C17 C7 Br2 -58.4(5) . . . . ?
C18 C17 S3 C24 -133.3(11) . . . . ?
C25 N1 C22 O1 175.0(4) . . . . ?
C25 N1 C22 C23 -3.1(5) . . . . ?
C25 N1 C26 C27 99.1(6) . . . . ?
C25 C24 S3 C17 -158.3(11) . . . . ?
C6 C1 C2 C3 -0.6(7) . . . . ?
C6 C5 C4 C3 -1.3(8) . . . . ?
C7 C17 C18 N2 -119.5(4) . . . . ?
C7 C17 C18 O4 59.1(7) . . . . ?
C7 C17 S3 C24 114.6(15) . . . . ?
C7 C8 C9 C10 178.8(5) . . . . ?
C7 C6 C5 C4 -176.4(5) . . . . ?
C2 C1 C6 C7 177.6(4) . . . . ?
C2 C1 C6 C5 -1.1(7) . . . . ?
C2 C3 C4 C5 -0.4(8) . . . . ?
C9 C8 C7 C17 119.3(5) . . . . ?
C9 C8 C7 C6 -125.4(5) . . . . ?
C9 C8 C7 Br2 -5.5(7) . . . . ?
C5 C6 C7 C17 -121.3(5) . . . . ?
C5 C6 C7 C8 123.7(5) . . . . ?
C5 C6 C7 Br2 -4.6(7) . . . . ?
C19 N2 C15 O3 -0.3(7) . . . . ?
C19 N2 C15 C16 -179.8(4) . . . . ?
C19 N2 C18 O4 3.2(8) . . . . ?
C19 N2 C18 C17 -178.2(4) . . . . ?
S3 C24 C25 N1 162.6(13) . . . . ?
S3 C24 C25 O2 -19.1(14) . . . . ?
S3 C17 C18 N2 143.1(14) . . . . ?
S3 C17 C18 O4 -38.4(15) . . . . ?
S3 C17 C7 C8 -76.0(6) . . . . ?
S3 C17 C7 C6 168.5(6) . . . . ?
S3 C17 C7 Br2 54.5(6) . . . . ?
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
-1.0103 -12.9180 2.7670 0.2570 0.0212 0.9662
2.3797 -5.1912 -5.1438 -0.9929 -0.0785 0.0895
2.4443 0.0211 -5.4901 -0.9616 -0.0763 -0.2636
-1.5820 12.3551 3.0762 0.7570 0.0593 -0.6508
-7.8573 -0.6279 -0.3763 -0.0789 0.9968 0.0090
7.8573 0.6279 0.3763 0.0789 -0.9968 -0.0090
6.6771 -6.5567 1.0461 0.0693 -0.8717 0.4852
7.9312 5.0115 -2.2537 -0.3049 -0.9000 -0.4193
-7.9314 -3.0111 2.2545 0.3403 0.8984 0.2903
-4.9757 -11.0080 1.1585 0.0077 0.5816 0.7582
-2.1770 -12.9965 -1.9096 -0.5646 0.3618 0.7424
2.6428 -6.9824 -5.0448 -1.0071 -0.1140 0.2103
6.8430 -4.9874 -3.2100 -0.6492 -0.7163 0.1777
6.7639 3.0178 -4.1940 -0.6805 -0.6719 -0.3868
2.3355 -6.0147 3.8764 0.5741 -0.4481 0.5802
3.2666 9.9927 2.8605 0.6786 -0.5349 -0.5006
