#------------------------------------------------------------------------------
#$Date: 2025-11-29 18:36:43 +0100 (Sat 29 de Nov de 2025) $
#$Revision: 303520 $
#$URL: svn://www.crystallography.net/cod/cif/1/57/57/1575717.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_1575717
loop_
_publ_author_name
'Marsh, Adam V.'
'White, Andrew J. P.'
'Heeney, Martin'
_publ_section_title
;
 The photoluminescence behaviour of monosubstituted non-benzenoid
 polycyclic-aromatic-substituted ortho-carboranes.
;
_journal_issue                   83
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              16222
_journal_page_last               16225
_journal_paper_doi               10.1039/d5cc02672e
_journal_volume                  61
_journal_year                    2025
_chemical_formula_moiety         'C12 H16 B10 S2'
_chemical_formula_sum            'C12 H16 B10 S2'
_chemical_formula_weight         332.47
_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
_audit_creation_method           SHELXL-2019/3
_audit_update_record
;
2025-04-30 deposited with the CCDC.	2025-09-12 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 96.026(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.0366(2)
_cell_length_b                   9.8201(4)
_cell_length_c                   23.1446(9)
_cell_measurement_reflns_used    1612
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      72.6770
_cell_measurement_theta_min      3.8280
_cell_volume                     1590.46(10)
_computing_cell_refinement       'CrysAlisPro, Rigaku OD'
_computing_data_collection       'CrysAlisPro, Rigaku OD'
_computing_data_reduction        'CrysAlisPro, Rigaku OD'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'CIFTAB-2014 (Sheldrick, 2017)'
_computing_structure_refinement  'SHELXL-2019/2 (Sheldrick, 2019)'
_computing_structure_solution    'SHELXS-2014 (Sheldrick, 2017)'
_diffrn_ambient_temperature      173(2)
_diffrn_detector_area_resol_mean 10.4115
_diffrn_measured_fraction_theta_full 0.983
_diffrn_measured_fraction_theta_max 0.947
_diffrn_measurement_device_type  'Agilent Xcalibur PX Ultra A'
_diffrn_measurement_method       'omega scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0394
_diffrn_reflns_av_unetI/netI     0.0548
_diffrn_reflns_Laue_measured_fraction_full 0.983
_diffrn_reflns_Laue_measured_fraction_max 0.947
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            5157
_diffrn_reflns_point_group_measured_fraction_full 0.983
_diffrn_reflns_point_group_measured_fraction_max 0.947
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.894
_diffrn_reflns_theta_min         3.841
_diffrn_source                   'Enhance Ultra (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    2.878
_exptl_absorpt_correction_T_max  0.971
_exptl_absorpt_correction_T_min  0.615
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
; 
CrysAlisPro 1.171.38.43 (Rigaku Oxford Diffraction, 2015) 
Analytical numeric absorption correction using a multifaceted crystal 
model based on expressions derived by R.C. Clark & J.S. Reid. 
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897) 
Empirical absorption correction using spherical harmonics, 
implemented in SCALE3 ABSPACK scaling algorithm. 
;
_exptl_crystal_colour            Colourless
_exptl_crystal_density_diffrn    1.388
_exptl_crystal_description       'platy needles'
_exptl_crystal_F_000             680
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.01
_refine_diff_density_max         0.545
_refine_diff_density_min         -0.310
_refine_diff_density_rms         0.069
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.068
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     242
_refine_ls_number_reflns         3046
_refine_ls_number_restraints     87
_refine_ls_restrained_S_all      1.070
_refine_ls_R_factor_all          0.0745
_refine_ls_R_factor_gt           0.0545
_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/[σ²(Fo²)+(0.0656P)²+1.0844P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1363
_refine_ls_wR_factor_ref         0.1505
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2347
_reflns_number_total             3046
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d5cc02672e2.cif
_cod_data_source_block           o-CbBDT
_cod_depositor_comments
'Adding full bibliography for 1575716--1575717.cif.'
_cod_original_cell_volume        1590.47(10)
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               1575717
_shelx_shelxl_version_number     2019/3
_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. 
;
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
C1 C 0.2503(4) 0.3423(3) 0.43036(12) 0.0205(6) Uani 1 1 d . . . . .
C2 C 0.2645(4) 0.2624(3) 0.48152(13) 0.0235(6) Uani 1 1 d D . . . .
S3 S 0.25268(19) 0.08547(10) 0.48913(4) 0.0270(3) Uani 0.904(3) 1 d D U P A 1
C4 C 0.2810(6) 0.0945(4) 0.56414(16) 0.0276(8) Uani 0.904(3) 1 d D U P A 1
H4A H 0.286118 0.016826 0.588746 0.033 Uiso 0.904(3) 1 calc R U P A 1
C5 C 0.2951(13) 0.2248(7) 0.5841(3) 0.0337(14) Uani 0.904(3) 1 d D U P A 1
H5A H 0.310315 0.247949 0.624182 0.040 Uiso 0.904(3) 1 calc R U P A 1
C3' C 0.231(8) 0.1171(16) 0.4887(9) 0.025(6) Uiso 0.096(3) 1 d D U P A 2
H3'A H 0.191315 0.057559 0.457392 0.029 Uiso 0.096(3) 1 calc R U P A 2
C4' C 0.263(6) 0.0760(14) 0.5451(8) 0.027(5) Uiso 0.096(3) 1 d D U P A 2
H4'A H 0.257920 -0.016551 0.556845 0.032 Uiso 0.096(3) 1 calc R U P A 2
S5' S 0.312(4) 0.2101(17) 0.5933(5) 0.035(4) Uiso 0.096(3) 1 d D U P A 2
C6 C 0.2846(4) 0.3236(3) 0.53822(13) 0.0244(6) Uani 1 1 d D . . . .
C7 C 0.2794(4) 0.4632(3) 0.54431(13) 0.0263(7) Uani 1 1 d . . . . .
H7A H 0.296140 0.504203 0.581672 0.032 Uiso 1 1 calc R U . . .
C8 C 0.2493(4) 0.5413(3) 0.49505(13) 0.0227(6) Uani 1 1 d D . . . .
S9 S 0.22141(16) 0.71747(11) 0.49458(4) 0.0271(3) Uani 0.904(3) 1 d D U P A 1
C10 C 0.1793(7) 0.7175(4) 0.41991(16) 0.0268(8) Uani 0.904(3) 1 d D U P A 1
H10A H 0.155580 0.798283 0.397723 0.032 Uiso 0.904(3) 1 calc R U P A 1
C11 C 0.1830(8) 0.5931(5) 0.3958(2) 0.0279(11) Uani 0.904(3) 1 d D U P A 1
H11A H 0.156771 0.577351 0.355289 0.034 Uiso 0.904(3) 1 calc R U P A 1
C9' C 0.251(8) 0.6869(16) 0.4938(10) 0.028(6) Uiso 0.096(3) 1 d D U P A 2
H9'A H 0.288571 0.743560 0.526225 0.034 Uiso 0.096(3) 1 calc R U P A 2
C10' C 0.187(8) 0.7346(15) 0.4374(9) 0.031(6) Uiso 0.096(3) 1 d D U P A 2
H10B H 0.141382 0.824006 0.428878 0.037 Uiso 0.096(3) 1 calc R U P A 2
S11' S 0.205(2) 0.6086(15) 0.3861(5) 0.029(3) Uiso 0.096(3) 1 d D U P A 2
C12 C 0.2309(4) 0.4848(3) 0.43780(13) 0.0211(6) Uani 1 1 d D . . . .
C13 C 0.2571(4) 0.2815(3) 0.37023(13) 0.0218(6) Uani 1 1 d . . . . .
C14 C 0.3314(4) 0.1218(3) 0.36349(13) 0.0238(6) Uani 1 1 d . . . . .
H14A H 0.377076 0.061232 0.403568 0.029 Uiso 1 1 calc R U . . .
B15 B 0.0908(5) 0.1555(4) 0.34838(15) 0.0244(7) Uani 1 1 d . . . . .
H15A H -0.024526 0.121692 0.375048 0.029 Uiso 1 1 calc R U . . .
B16 B 0.0873(5) 0.3164(4) 0.31360(15) 0.0247(7) Uani 1 1 d . . . . .
H16A H -0.032270 0.390400 0.316809 0.030 Uiso 1 1 calc R U . . .
B17 B 0.3299(5) 0.3719(4) 0.31213(15) 0.0248(7) Uani 1 1 d . . . . .
H17A H 0.369701 0.482336 0.314189 0.030 Uiso 1 1 calc R U . . .
B18 B 0.4825(5) 0.2475(4) 0.34701(15) 0.0231(7) Uani 1 1 d . . . . .
H18A H 0.620731 0.274314 0.372967 0.028 Uiso 1 1 calc R U . . .
B19 B 0.2121(5) 0.0395(4) 0.30674(15) 0.0259(7) Uani 1 1 d . . . . .
H19A H 0.175086 -0.071471 0.305995 0.031 Uiso 1 1 calc R U . . .
B20 B 0.0561(5) 0.1636(4) 0.27174(16) 0.0269(7) Uani 1 1 d . . . . .
H20A H -0.083914 0.136171 0.246900 0.032 Uiso 1 1 calc R U . . .
B21 B 0.2041(5) 0.2980(4) 0.24929(15) 0.0250(7) Uani 1 1 d . . . . .
H21A H 0.160196 0.359639 0.209408 0.030 Uiso 1 1 calc R U . . .
B22 B 0.4492(5) 0.2544(4) 0.27029(15) 0.0240(7) Uani 1 1 d . . . . .
H22A H 0.567243 0.286624 0.244398 0.029 Uiso 1 1 calc R U . . .
B23 B 0.4525(5) 0.0946(4) 0.30516(15) 0.0255(7) Uani 1 1 d . . . . .
H23A H 0.572279 0.020195 0.303078 0.031 Uiso 1 1 calc R U . . .
B24 B 0.2812(5) 0.1262(4) 0.24486(16) 0.0262(7) Uani 1 1 d . . . . .
H24A H 0.288212 0.073963 0.202108 0.031 Uiso 1 1 calc R U . . .
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'
B B 0.0090 0.0039 '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_
_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 C12 116.4(3) . . ?
C2 C1 C13 122.8(3) . . ?
C12 C1 C13 120.8(3) . . ?
C1 C2 C6 121.6(3) . . ?
C1 C2 C3' 129.7(8) . . ?
C6 C2 C3' 107.9(8) . . ?
C1 C2 S3 129.4(2) . . ?
C6 C2 S3 108.9(2) . . ?
C4 S3 C2 92.79(16) . . ?
C5 C4 S3 112.7(3) . . ?
C4 C5 C6 112.9(5) . . ?
C4' C3' C2 112.8(11) . . ?
C3' C4' S5' 113.1(9) . . ?
C6 S5' C4' 90.9(6) . . ?
C7 C6 C5 126.6(4) . . ?
C7 C6 C2 120.5(3) . . ?
C5 C6 C2 112.7(4) . . ?
C7 C6 S5' 125.5(6) . . ?
C2 C6 S5' 113.9(6) . . ?
C8 C7 C6 118.3(3) . . ?
C7 C8 C12 123.0(3) . . ?
C7 C8 C9' 125.1(9) . . ?
C12 C8 C9' 111.6(9) . . ?
C7 C8 S9 124.6(2) . . ?
C12 C8 S9 112.4(2) . . ?
C10 S9 C8 90.80(16) . . ?
C11 C10 S9 114.0(3) . . ?
C10 C11 C12 113.6(4) . . ?
C10' C9' C8 110.4(14) . . ?
C9' C10' S11' 111.1(13) . . ?
C12 S11' C10' 92.2(7) . . ?
C1 C12 C8 119.6(3) . . ?
C1 C12 C11 131.2(3) . . ?
C8 C12 C11 109.1(3) . . ?
C1 C12 S11' 128.6(5) . . ?
C8 C12 S11' 111.6(5) . . ?
C1 C13 C14 119.7(2) . . ?
C1 C13 B16 122.4(2) . . ?
C14 C13 B16 108.5(2) . . ?
C1 C13 B17 123.3(3) . . ?
C14 C13 B17 106.8(2) . . ?
B16 C13 B17 62.82(19) . . ?
C1 C13 B15 117.4(2) . . ?
C14 C13 B15 60.76(19) . . ?
B16 C13 B15 61.73(19) . . ?
B17 C13 B15 112.5(2) . . ?
C1 C13 B18 118.1(2) . . ?
C14 C13 B18 59.39(18) . . ?
B16 C13 B18 112.5(2) . . ?
B17 C13 B18 60.70(18) . . ?
B15 C13 B18 112.1(2) . . ?
C13 C14 B19 112.8(2) . . ?
C13 C14 B23 114.4(2) . . ?
B19 C14 B23 63.5(2) . . ?
C13 C14 B18 63.04(18) . . ?
B19 C14 B18 116.4(2) . . ?
B23 C14 B18 63.6(2) . . ?
C13 C14 B15 61.78(18) . . ?
B19 C14 B15 62.4(2) . . ?
B23 C14 B15 115.8(2) . . ?
B18 C14 B15 116.1(2) . . ?
C14 B15 C13 57.45(17) . . ?
C14 B15 B20 104.0(2) . . ?
C13 B15 B20 106.1(2) . . ?
C14 B15 B19 57.79(19) . . ?
C13 B15 B19 105.5(2) . . ?
B20 B15 B19 60.4(2) . . ?
C14 B15 B16 103.3(2) . . ?
C13 B15 B16 58.35(18) . . ?
B20 B15 B16 60.6(2) . . ?
B19 B15 B16 108.1(2) . . ?
C13 B16 B15 59.92(19) . . ?
C13 B16 B21 105.8(2) . . ?
B15 B16 B21 107.6(2) . . ?
C13 B16 B20 106.4(2) . . ?
B15 B16 B20 59.5(2) . . ?
B21 B16 B20 60.2(2) . . ?
C13 B16 B17 59.14(18) . . ?
B15 B16 B17 108.1(2) . . ?
B21 B16 B17 59.50(19) . . ?
B20 B16 B17 107.9(2) . . ?
C13 B17 B18 60.38(18) . . ?
C13 B17 B22 106.6(2) . . ?
B18 B17 B22 59.9(2) . . ?
C13 B17 B21 105.3(2) . . ?
B18 B17 B21 108.6(3) . . ?
B22 B17 B21 60.7(2) . . ?
C13 B17 B16 58.04(18) . . ?
B18 B17 B16 108.4(2) . . ?
B22 B17 B16 108.6(3) . . ?
B21 B17 B16 59.90(19) . . ?
C14 B18 C13 57.57(17) . . ?
C14 B18 B17 103.9(2) . . ?
C13 B18 B17 58.92(17) . . ?
C14 B18 B22 103.5(2) . . ?
C13 B18 B22 105.7(2) . . ?
B17 B18 B22 60.3(2) . . ?
C14 B18 B23 58.01(18) . . ?
C13 B18 B23 105.4(2) . . ?
B17 B18 B23 107.6(2) . . ?
B22 B18 B23 59.5(2) . . ?
C14 B19 B15 59.78(19) . . ?
C14 B19 B24 104.0(2) . . ?
B15 B19 B24 108.6(3) . . ?
C14 B19 B20 105.0(3) . . ?
B15 B19 B20 59.7(2) . . ?
B24 B19 B20 60.8(2) . . ?
C14 B19 B23 58.33(19) . . ?
B15 B19 B23 109.3(3) . . ?
B24 B19 B23 59.8(2) . . ?
B20 B19 B23 109.0(3) . . ?
B15 B20 B19 59.9(2) . . ?
B15 B20 B16 59.8(2) . . ?
B19 B20 B16 107.1(2) . . ?
B15 B20 B21 107.5(2) . . ?
B19 B20 B21 106.7(2) . . ?
B16 B20 B21 59.8(2) . . ?
B15 B20 B24 107.7(2) . . ?
B19 B20 B24 59.6(2) . . ?
B16 B20 B24 107.3(2) . . ?
B21 B20 B24 59.38(19) . . ?
B17 B21 B24 107.8(2) . . ?
B17 B21 B16 60.60(19) . . ?
B24 B21 B16 108.3(3) . . ?
B17 B21 B20 108.6(2) . . ?
B24 B21 B20 60.5(2) . . ?
B16 B21 B20 60.0(2) . . ?
B17 B21 B22 59.57(19) . . ?
B24 B21 B22 59.9(2) . . ?
B16 B21 B22 108.2(2) . . ?
B20 B21 B22 108.5(3) . . ?
B23 B22 B18 60.8(2) . . ?
B23 B22 B17 108.3(2) . . ?
B18 B22 B17 59.79(19) . . ?
B23 B22 B24 60.0(2) . . ?
B18 B22 B24 108.5(2) . . ?
B17 B22 B24 107.7(2) . . ?
B23 B22 B21 107.6(2) . . ?
B18 B22 B21 107.7(2) . . ?
B17 B22 B21 59.73(19) . . ?
B24 B22 B21 59.6(2) . . ?
C14 B23 B22 103.9(2) . . ?
C14 B23 B24 104.0(2) . . ?
B22 B23 B24 60.6(2) . . ?
C14 B23 B19 58.13(19) . . ?
B22 B23 B19 108.2(2) . . ?
B24 B23 B19 60.0(2) . . ?
C14 B23 B18 58.37(18) . . ?
B22 B23 B18 59.7(2) . . ?
B24 B23 B18 108.1(3) . . ?
B19 B23 B18 107.6(2) . . ?
B23 B24 B19 60.2(2) . . ?
B23 B24 B21 107.9(3) . . ?
B19 B24 B21 107.3(2) . . ?
B23 B24 B22 59.4(2) . . ?
B19 B24 B22 107.5(2) . . ?
B21 B24 B22 60.5(2) . . ?
B23 B24 B20 108.3(2) . . ?
B19 B24 B20 59.6(2) . . ?
B21 B24 B20 60.1(2) . . ?
B22 B24 B20 108.6(2) . . ?
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 C2 1.415(4) . ?
C1 C12 1.418(4) . ?
C1 C13 1.520(4) . ?
C2 C6 1.437(4) . ?
C2 C3' 1.459(15) . ?
C2 S3 1.750(3) . ?
S3 C4 1.729(4) . ?
C4 C5 1.361(7) . ?
C5 C6 1.435(7) . ?
C3' C4' 1.362(16) . ?
C4' S5' 1.738(15) . ?
S5' C6 1.690(12) . ?
C6 C7 1.379(5) . ?
C7 C8 1.372(4) . ?
C8 C12 1.430(4) . ?
C8 C9' 1.430(16) . ?
C8 S9 1.741(3) . ?
S9 C10 1.723(4) . ?
C10 C11 1.344(6) . ?
C11 C12 1.456(6) . ?
C9' C10' 1.41(3) . ?
C10' S11' 1.729(16) . ?
S11' C12 1.702(11) . ?
C13 C14 1.666(4) . ?
C13 B16 1.713(4) . ?
C13 B17 1.733(4) . ?
C13 B15 1.741(5) . ?
C13 B18 1.759(4) . ?
C14 B19 1.688(5) . ?
C14 B23 1.692(4) . ?
C14 B18 1.699(4) . ?
C14 B15 1.724(4) . ?
B15 B20 1.767(5) . ?
B15 B19 1.769(5) . ?
B15 B16 1.772(5) . ?
B16 B21 1.784(5) . ?
B16 B20 1.787(5) . ?
B16 B17 1.796(5) . ?
B17 B18 1.765(5) . ?
B17 B22 1.773(5) . ?
B17 B21 1.776(5) . ?
B18 B22 1.768(5) . ?
B18 B23 1.787(5) . ?
B19 B24 1.777(5) . ?
B19 B20 1.778(5) . ?
B19 B23 1.780(5) . ?
B20 B21 1.792(5) . ?
B20 B24 1.800(5) . ?
B21 B24 1.779(5) . ?
B21 B22 1.794(5) . ?
B22 B23 1.764(5) . ?
B22 B24 1.784(5) . ?
B23 B24 1.773(5) . ?
