#------------------------------------------------------------------------------
#$Date: 2025-08-21 14:03:24 +0200 (Thu 21 de Aug de 2025) $
#$Revision: 301848 $
#$URL: svn://www.crystallography.net/cod/cif/7/02/06/7020633.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_7020633
loop_
_publ_author_name
'Rao, Ying-Li'
'Amarne, Hazem'
'Lu, Jia-Sheng'
'Wang, Suning'
_publ_section_title
;
 Impact of a dithienyl unit on photostability of N,C-chelating boron
 compounds.
;
_journal_issue                   3
_journal_name_full
'Dalton transactions (Cambridge, England : 2003)'
_journal_page_first              638
_journal_page_last               644
_journal_paper_doi               10.1039/c2dt31370g
_journal_volume                  42
_journal_year                    2013
_chemical_formula_sum            'C36 H33 B Cl2 N S'
_chemical_formula_weight         593.40
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 108.141(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   13.9623(15)
_cell_length_b                   26.777(3)
_cell_length_c                   8.7487(8)
_cell_measurement_reflns_used    4616
_cell_measurement_temperature    180(2)
_cell_measurement_theta_max      22.02
_cell_measurement_theta_min      2.16
_cell_volume                     3108.3(6)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      180(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0795
_diffrn_reflns_av_sigmaI/netI    0.0516
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       33
_diffrn_reflns_limit_k_min       -33
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            42368
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_min         1.52
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.302
_exptl_absorpt_correction_T_max  0.9850
_exptl_absorpt_correction_T_min  0.9704
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_density_diffrn    1.268
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1244
_exptl_crystal_size_max          0.10
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.384
_refine_diff_density_min         -0.458
_refine_diff_density_rms         0.048
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     376
_refine_ls_number_reflns         6119
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.056
_refine_ls_R_factor_all          0.1098
_refine_ls_R_factor_gt           0.0566
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0500P)²+2.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1190
_refine_ls_wR_factor_ref         0.1443
_reflns_number_gt                3743
_reflns_number_total             6119
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c2dt31370g.txt
_cod_data_source_block           louis49
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 1891 2012-01-12 08:04:46Z andrius 
;
_cod_original_cell_volume        3108.3(5)
_cod_original_sg_symbol_H-M      P2(1)/c
_cod_database_code               7020633
loop_
_symmetry_equiv_pos_as_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
S1 S 0.92996(6) 0.02661(4) 0.25525(13) 0.0670(3) Uani 1 1 d .
N1 N 0.71163(16) 0.06512(8) -0.5471(3) 0.0342(5) Uani 1 1 d .
B1 B 0.6788(2) 0.12253(11) -0.6213(4) 0.0301(7) Uani 1 1 d .
Cl1 Cl 1.69479(8) -0.13891(4) 2.11915(12) 0.0808(3) Uani 1 1 d .
Cl2 Cl 1.79305(9) -0.15448(4) 1.87537(14) 0.0870(4) Uani 1 1 d .
C1 C 0.6389(2) 0.10463(11) -0.8071(3) 0.0370(7) Uani 1 1 d .
C2 C 0.5887(2) 0.13070(14) -0.9463(4) 0.0501(8) Uani 1 1 d .
H2A H 0.5746 0.1652 -0.9404 0.060 Uiso 1 1 calc R
C3 C 0.5590(3) 0.10639(19) -1.0941(4) 0.0723(12) Uani 1 1 d .
H3A H 0.5264 0.1248 -1.1889 0.087 Uiso 1 1 calc R
C4 C 0.5761(3) 0.0558(2) -1.1054(5) 0.0877(16) Uani 1 1 d .
H4A H 0.5559 0.0399 -1.2075 0.105 Uiso 1 1 calc R
C5 C 0.6218(3) 0.02876(16) -0.9705(5) 0.0721(12) Uani 1 1 d .
H5A H 0.6325 -0.0061 -0.9772 0.086 Uiso 1 1 calc R
C6 C 0.6528(2) 0.05334(12) -0.8217(4) 0.0451(8) Uani 1 1 d .
C7 C 0.6987(2) 0.03059(11) -0.6661(4) 0.0436(8) Uani 1 1 d .
C8 C 0.7280(3) -0.01874(12) -0.6278(5) 0.0587(10) Uani 1 1 d .
H8A H 0.7184 -0.0429 -0.7109 0.070 Uiso 1 1 calc R
C9 C 0.7706(3) -0.03255(12) -0.4705(6) 0.0636(11) Uani 1 1 d .
H9A H 0.7911 -0.0661 -0.4442 0.076 Uiso 1 1 calc R
C10 C 0.7837(2) 0.00296(12) -0.3492(5) 0.0509(9) Uani 1 1 d .
C11 C 0.7538(2) 0.05159(11) -0.3944(4) 0.0411(7) Uani 1 1 d .
H11A H 0.7638 0.0763 -0.3130 0.049 Uiso 1 1 calc R
C12 C 0.8275(2) -0.00823(13) -0.1818(5) 0.0645(11) Uani 1 1 d .
C13 C 0.8663(2) -0.01662(13) -0.0426(6) 0.0670(12) Uani 1 1 d .
C14 C 0.9113(2) -0.02394(13) 0.1256(5) 0.0655(11) Uani 1 1 d .
C15 C 0.9472(3) -0.06713(14) 0.2083(5) 0.0731(13) Uani 1 1 d .
H15A H 0.9447 -0.0988 0.1585 0.088 Uiso 1 1 calc R
C16 C 0.9879(2) -0.05930(14) 0.3739(5) 0.0702(12) Uani 1 1 d .
H16A H 1.0161 -0.0855 0.4475 0.084 Uiso 1 1 calc R
C17 C 0.9837(2) -0.01093(13) 0.4211(4) 0.0617(11) Uani 1 1 d .
C18 C 0.78624(19) 0.15307(9) -0.5490(3) 0.0274(6) Uani 1 1 d .
C19 C 0.8534(2) 0.16265(9) -0.6392(3) 0.0320(6) Uani 1 1 d .
C20 C 0.9465(2) 0.18548(10) -0.5672(4) 0.0383(7) Uani 1 1 d .
H20A H 0.9898 0.1909 -0.6304 0.046 Uiso 1 1 calc R
C21 C 0.9783(2) 0.20049(11) -0.4088(4) 0.0406(7) Uani 1 1 d .
C22 C 0.9132(2) 0.19226(10) -0.3212(4) 0.0384(7) Uani 1 1 d .
H22A H 0.9329 0.2025 -0.2118 0.046 Uiso 1 1 calc R
C23 C 0.8190(2) 0.16945(10) -0.3872(3) 0.0318(6) Uani 1 1 d .
C24 C 0.7570(2) 0.16703(12) -0.2731(3) 0.0418(7) Uani 1 1 d .
H24A H 0.7965 0.1509 -0.1727 0.063 Uiso 1 1 calc R
H24B H 0.6956 0.1477 -0.3226 0.063 Uiso 1 1 calc R
H24C H 0.7389 0.2009 -0.2502 0.063 Uiso 1 1 calc R
C25 C 1.0787(2) 0.22569(15) -0.3349(5) 0.0665(11) Uani 1 1 d .
H25A H 1.1312 0.2072 -0.3637 0.100 Uiso 1 1 calc R
H25B H 1.0947 0.2262 -0.2176 0.100 Uiso 1 1 calc R
H25C H 1.0756 0.2600 -0.3752 0.100 Uiso 1 1 calc R
C26 C 0.8290(2) 0.15220(11) -0.8175(3) 0.0427(7) Uani 1 1 d .
H26A H 0.8893 0.1576 -0.8500 0.064 Uiso 1 1 calc R
H26B H 0.7753 0.1747 -0.8783 0.064 Uiso 1 1 calc R
H26C H 0.8065 0.1175 -0.8396 0.064 Uiso 1 1 calc R
C27 C 0.58017(19) 0.14603(9) -0.5817(3) 0.0275(6) Uani 1 1 d .
C28 C 0.5627(2) 0.19832(10) -0.5947(3) 0.0318(6) Uani 1 1 d .
C29 C 0.4802(2) 0.21971(10) -0.5629(3) 0.0362(7) Uani 1 1 d .
H29A H 0.4714 0.2549 -0.5729 0.043 Uiso 1 1 calc R
C30 C 0.4105(2) 0.19166(10) -0.5173(3) 0.0370(7) Uani 1 1 d .
C31 C 0.4231(2) 0.14038(10) -0.5138(3) 0.0350(7) Uani 1 1 d .
H31A H 0.3752 0.1200 -0.4863 0.042 Uiso 1 1 calc R
C32 C 0.5038(2) 0.11737(10) -0.5491(3) 0.0315(6) Uani 1 1 d .
C33 C 0.6314(2) 0.23419(10) -0.6449(4) 0.0424(8) Uani 1 1 d .
H33A H 0.5936 0.2643 -0.6911 0.064 Uiso 1 1 calc R
H33B H 0.6568 0.2182 -0.7253 0.064 Uiso 1 1 calc R
H33C H 0.6882 0.2433 -0.5507 0.064 Uiso 1 1 calc R
C34 C 0.3228(2) 0.21575(13) -0.4783(4) 0.0520(9) Uani 1 1 d .
H34A H 0.2956 0.2430 -0.5543 0.078 Uiso 1 1 calc R
H34B H 0.3460 0.2291 -0.3686 0.078 Uiso 1 1 calc R
H34C H 0.2702 0.1908 -0.4866 0.078 Uiso 1 1 calc R
C35 C 0.5001(2) 0.06098(10) -0.5584(4) 0.0421(7) Uani 1 1 d .
H35A H 0.4353 0.0492 -0.5505 0.063 Uiso 1 1 calc R
H35B H 0.5550 0.0470 -0.4697 0.063 Uiso 1 1 calc R
H35C H 0.5075 0.0501 -0.6611 0.063 Uiso 1 1 calc R
C36 C 1.6873(3) -0.13126(16) 1.9179(5) 0.0788(13) Uani 1 1 d .
H36A H 1.6799 -0.0953 1.8907 0.095 Uiso 1 1 calc R
H36B H 1.6264 -0.1486 1.8494 0.095 Uiso 1 1 calc R
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 '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 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 '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
C17 S1 C14 91.86(18) . .
C11 N1 C7 119.6(3) . .
C11 N1 B1 128.3(2) . .
C7 N1 B1 111.8(2) . .
C1 B1 C27 106.0(2) . .
C1 B1 C18 121.2(2) . .
C27 B1 C18 116.7(2) . .
C1 B1 N1 94.8(2) . .
C27 B1 N1 114.5(2) . .
C18 B1 N1 101.5(2) . .
C2 C1 C6 117.4(3) . .
C2 C1 B1 130.8(3) . .
C6 C1 B1 111.6(3) . .
C1 C2 C3 120.2(4) . .
C1 C2 H2A 119.9 . .
C3 C2 H2A 119.9 . .
C4 C3 C2 121.1(4) . .
C4 C3 H3A 119.5 . .
C2 C3 H3A 119.5 . .
C5 C4 C3 120.2(4) . .
C5 C4 H4A 119.9 . .
C3 C4 H4A 119.9 . .
C4 C5 C6 118.7(4) . .
C4 C5 H5A 120.6 . .
C6 C5 H5A 120.6 . .
C1 C6 C5 122.3(3) . .
C1 C6 C7 111.2(3) . .
C5 C6 C7 126.5(3) . .
N1 C7 C8 120.1(3) . .
N1 C7 C6 110.3(3) . .
C8 C7 C6 129.6(3) . .
C9 C8 C7 120.1(3) . .
C9 C8 H8A 120.0 . .
C7 C8 H8A 120.0 . .
C8 C9 C10 119.6(3) . .
C8 C9 H9A 120.2 . .
C10 C9 H9A 120.2 . .
C11 C10 C9 117.8(3) . .
C11 C10 C12 118.9(3) . .
C9 C10 C12 123.3(3) . .
N1 C11 C10 122.8(3) . .
N1 C11 H11A 118.6 . .
C10 C11 H11A 118.6 . .
C13 C12 C10 178.0(4) . .
C12 C13 C14 176.9(4) . .
C15 C14 C13 129.2(4) . .
C15 C14 S1 110.9(3) . .
C13 C14 S1 119.8(3) . .
C14 C15 C16 112.6(4) . .
C14 C15 H15A 123.7 . .
C16 C15 H15A 123.7 . .
C17 C16 C15 114.5(3) . .
C17 C16 H16A 122.8 . .
C15 C16 H16A 122.8 . .
C16 C17 C17 130.2(4) . 3_756
C16 C17 S1 110.2(3) . .
C17 C17 S1 119.6(4) 3_756 .
C23 C18 C19 115.8(2) . .
C23 C18 B1 120.6(2) . .
C19 C18 B1 123.6(2) . .
C20 C19 C18 120.7(3) . .
C20 C19 C26 115.1(2) . .
C18 C19 C26 124.1(2) . .
C21 C20 C19 123.1(3) . .
C21 C20 H20A 118.5 . .
C19 C20 H20A 118.5 . .
C20 C21 C22 116.8(3) . .
C20 C21 C25 121.9(3) . .
C22 C21 C25 121.3(3) . .
C21 C22 C23 122.6(3) . .
C21 C22 H22A 118.7 . .
C23 C22 H22A 118.7 . .
C22 C23 C18 121.1(3) . .
C22 C23 C24 113.8(2) . .
C18 C23 C24 125.0(2) . .
C23 C24 H24A 109.5 . .
C23 C24 H24B 109.5 . .
H24A C24 H24B 109.5 . .
C23 C24 H24C 109.5 . .
H24A C24 H24C 109.5 . .
H24B C24 H24C 109.5 . .
C21 C25 H25A 109.5 . .
C21 C25 H25B 109.5 . .
H25A C25 H25B 109.5 . .
C21 C25 H25C 109.5 . .
H25A C25 H25C 109.5 . .
H25B C25 H25C 109.5 . .
C19 C26 H26A 109.5 . .
C19 C26 H26B 109.5 . .
H26A C26 H26B 109.5 . .
C19 C26 H26C 109.5 . .
H26A C26 H26C 109.5 . .
H26B C26 H26C 109.5 . .
C32 C27 C28 115.5(2) . .
C32 C27 B1 124.6(2) . .
C28 C27 B1 119.6(2) . .
C29 C28 C27 121.5(2) . .
C29 C28 C33 115.8(2) . .
C27 C28 C33 122.7(2) . .
C30 C29 C28 122.4(3) . .
C30 C29 H29A 118.8 . .
C28 C29 H29A 118.8 . .
C29 C30 C31 116.7(3) . .
C29 C30 C34 121.7(3) . .
C31 C30 C34 121.6(3) . .
C30 C31 C32 122.5(3) . .
C30 C31 H31A 118.8 . .
C32 C31 H31A 118.8 . .
C31 C32 C27 121.0(2) . .
C31 C32 C35 115.8(2) . .
C27 C32 C35 123.1(2) . .
C28 C33 H33A 109.5 . .
C28 C33 H33B 109.5 . .
H33A C33 H33B 109.5 . .
C28 C33 H33C 109.5 . .
H33A C33 H33C 109.5 . .
H33B C33 H33C 109.5 . .
C30 C34 H34A 109.5 . .
C30 C34 H34B 109.5 . .
H34A C34 H34B 109.5 . .
C30 C34 H34C 109.5 . .
H34A C34 H34C 109.5 . .
H34B C34 H34C 109.5 . .
C32 C35 H35A 109.5 . .
C32 C35 H35B 109.5 . .
H35A C35 H35B 109.5 . .
C32 C35 H35C 109.5 . .
H35A C35 H35C 109.5 . .
H35B C35 H35C 109.5 . .
Cl1 C36 Cl2 112.6(2) . .
Cl1 C36 H36A 109.1 . .
Cl2 C36 H36A 109.1 . .
Cl1 C36 H36B 109.1 . .
Cl2 C36 H36B 109.1 . .
H36A C36 H36B 107.8 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
S1 C17 1.732(3) .
S1 C14 1.733(4) .
N1 C11 1.331(4) .
N1 C7 1.362(4) .
N1 B1 1.676(4) .
B1 C1 1.619(4) .
B1 C27 1.646(4) .
B1 C18 1.652(4) .
Cl1 C36 1.743(4) .
Cl2 C36 1.746(4) .
C1 C2 1.389(4) .
C1 C6 1.398(4) .
C2 C3 1.391(5) .
C2 H2A 0.9500 .
C3 C4 1.383(6) .
C3 H3A 0.9500 .
C4 C5 1.363(6) .
C4 H4A 0.9500 .
C5 C6 1.402(4) .
C5 H5A 0.9500 .
C6 C7 1.446(4) .
C7 C8 1.392(4) .
C8 C9 1.369(5) .
C8 H8A 0.9500 .
C9 C10 1.394(5) .
C9 H9A 0.9500 .
C10 C11 1.387(4) .
C10 C12 1.432(5) .
C11 H11A 0.9500 .
C12 C13 1.190(5) .
C13 C14 1.422(6) .
C14 C15 1.373(4) .
C15 C16 1.397(6) .
C15 H15A 0.9500 .
C16 C17 1.366(5) .
C16 H16A 0.9500 .
C17 C17 1.437(8) 3_756
C18 C23 1.415(4) .
C18 C19 1.424(4) .
C19 C20 1.396(4) .
C19 C26 1.516(4) .
C20 C21 1.376(4) .
C20 H20A 0.9500 .
C21 C22 1.377(4) .
C21 C25 1.508(4) .
C22 C23 1.401(4) .
C22 H22A 0.9500 .
C23 C24 1.512(4) .
C24 H24A 0.9800 .
C24 H24B 0.9800 .
C24 H24C 0.9800 .
C25 H25A 0.9800 .
C25 H25B 0.9800 .
C25 H25C 0.9800 .
C26 H26A 0.9800 .
C26 H26B 0.9800 .
C26 H26C 0.9800 .
C27 C32 1.413(4) .
C27 C28 1.419(4) .
C28 C29 1.390(4) .
C28 C33 1.515(4) .
C29 C30 1.383(4) .
C29 H29A 0.9500 .
C30 C31 1.384(4) .
C30 C34 1.514(4) .
C31 C32 1.400(4) .
C31 H31A 0.9500 .
C32 C35 1.512(4) .
C33 H33A 0.9800 .
C33 H33B 0.9800 .
C33 H33C 0.9800 .
C34 H34A 0.9800 .
C34 H34B 0.9800 .
C34 H34C 0.9800 .
C35 H35A 0.9800 .
C35 H35B 0.9800 .
C35 H35C 0.9800 .
C36 H36A 0.9900 .
C36 H36B 0.9900 .
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139159078
