#------------------------------------------------------------------------------
#$Date: 2021-11-11 01:16:10 +0200 (Thu, 11 Nov 2021) $
#$Revision: 270584 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/56/51/1565184.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_1565184
loop_
_publ_author_name
'Feng, Zhongtao'
'Chong, Yuanyuan'
'Tang, Shuxuan'
'Fang, Yong'
'Zhao, Yue'
'Jiang, Jun'
'Wang, Xinping'
_publ_section_title
;
 A stable triplet diradical emitter
;
_journal_name_full               'Chemical Science'
_journal_paper_doi               10.1039/D1SC04486A
_journal_year                    2021
_chemical_formula_moiety         'C40 H4 B2 Br2 F20 O4'
_chemical_formula_sum            'C40 H4 B2 Br2 F20 O4'
_chemical_formula_weight         1109.87
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2020-09-03
_audit_creation_method
;
Olex2 1.3
(compiled 2020.07.31 svn.rc2a77460 for OlexSys, GUI svn.r6145)
;
_audit_update_record
;
2021-04-24 deposited with the CCDC.	2021-11-05 downloaded from the CCDC.
;
_cell_angle_alpha                65.579(2)
_cell_angle_beta                 79.789(2)
_cell_angle_gamma                78.572(2)
_cell_formula_units_Z            1
_cell_length_a                   9.4968(4)
_cell_length_b                   12.6034(7)
_cell_length_c                   12.6524(6)
_cell_measurement_reflns_used    4045
_cell_measurement_temperature    196
_cell_measurement_theta_max      26.48
_cell_measurement_theta_min      2.60
_cell_volume                     1343.83(12)
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      196
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0321
_diffrn_reflns_av_unetI/netI     0.0488
_diffrn_reflns_Laue_measured_fraction_full 0.989
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            12607
_diffrn_reflns_point_group_measured_fraction_full 0.989
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.482
_diffrn_reflns_theta_min         2.604
_diffrn_source_current           40.0
_diffrn_source_power             2.0
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.610
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6744
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0764 before and 0.0402 after correction.
The Ratio of minimum to maximum transmission is 0.9045.
The λ/2 correction factor is Not present.
;
_exptl_crystal_colour            red
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.371
_exptl_crystal_description       needle
_exptl_crystal_F_000             536
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.363
_refine_diff_density_min         -0.646
_refine_diff_density_rms         0.049
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     307
_refine_ls_number_reflns         6119
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.040
_refine_ls_R_factor_all          0.0595
_refine_ls_R_factor_gt           0.0395
_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)+(0.0428P)²+0.2516P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0957
_refine_ls_wR_factor_ref         0.1035
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4366
_reflns_number_total             6119
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d1sc04486a2.cif
_cod_data_source_block           200903fzt01_0m_a_sq
_cod_database_code               1565184
_shelx_shelxl_version_number     2018/3
_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.
;
_shelx_estimated_absorpt_t_max   0.856
_shelx_estimated_absorpt_t_min   0.739
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C4(H4), C6(H6)
;
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'
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
B1 B 0.2179(3) 0.3343(2) 0.3040(2) 0.0340(6) Uani 1 1 d . . . . .
Br1 Br -0.15163(3) 0.11485(3) 0.87720(2) 0.05986(12) Uani 1 1 d . . . . .
C1 C 0.1319(2) 0.16139(19) 0.34780(18) 0.0317(5) Uani 1 1 d . . . . .
C2 C 0.0949(2) 0.19055(19) 0.44547(18) 0.0315(5) Uani 1 1 d . . . . .
C3 C 0.0173(2) 0.11908(19) 0.54973(18) 0.0305(5) Uani 1 1 d . . . . .
C4 C -0.0218(2) 0.1487(2) 0.64714(19) 0.0369(5) Uani 1 1 d . . . . .
H4 H 0.002559 0.219011 0.645398 0.044 Uiso 1 1 calc R U . . .
C5 C -0.0963(3) 0.0748(2) 0.74604(18) 0.0382(5) Uani 1 1 d . . . . .
C6 C -0.1329(2) -0.0279(2) 0.75065(18) 0.0372(5) Uani 1 1 d . . . . .
H6 H -0.183851 -0.077797 0.819198 0.045 Uiso 1 1 calc R U . . .
C7 C -0.0944(2) -0.05772(19) 0.65377(18) 0.0309(5) Uani 1 1 d . . . . .
C8 C -0.0190(2) 0.01505(19) 0.55022(17) 0.0295(5) Uani 1 1 d . . . . .
C9 C 0.3863(2) 0.3329(2) 0.31064(19) 0.0363(5) Uani 1 1 d . . . . .
C10 C 0.4625(3) 0.4283(2) 0.2534(2) 0.0407(6) Uani 1 1 d . . . . .
C11 C 0.6061(3) 0.4233(2) 0.2643(2) 0.0460(6) Uani 1 1 d . . . . .
C12 C 0.6788(3) 0.3210(3) 0.3348(2) 0.0530(7) Uani 1 1 d . . . . .
C13 C 0.6102(3) 0.2245(3) 0.3935(2) 0.0554(7) Uani 1 1 d . . . . .
C14 C 0.4672(3) 0.2320(2) 0.3794(2) 0.0468(6) Uani 1 1 d . . . . .
C15 C 0.1286(2) 0.4569(2) 0.22413(19) 0.0350(5) Uani 1 1 d . . . . .
C16 C 0.1462(3) 0.4949(2) 0.1040(2) 0.0453(6) Uani 1 1 d . . . . .
C17 C 0.0728(4) 0.5972(2) 0.0309(2) 0.0545(7) Uani 1 1 d . . . . .
C18 C -0.0250(3) 0.6663(2) 0.0782(3) 0.0562(8) Uani 1 1 d . . . . .
C19 C -0.0449(3) 0.6334(2) 0.1961(3) 0.0488(6) Uani 1 1 d . . . . .
C20 C 0.0318(3) 0.5301(2) 0.2669(2) 0.0412(6) Uani 1 1 d . . . . .
F1 F 0.39746(16) 0.53208(13) 0.18419(14) 0.0565(4) Uani 1 1 d . . . . .
F2 F 0.67297(17) 0.51891(15) 0.20712(14) 0.0635(5) Uani 1 1 d . . . . .
F3 F 0.81901(16) 0.31570(18) 0.34663(16) 0.0764(6) Uani 1 1 d . . . . .
F4 F 0.68213(19) 0.12303(17) 0.46220(18) 0.0872(7) Uani 1 1 d . . . . .
F5 F 0.40541(16) 0.13288(13) 0.43857(15) 0.0635(5) Uani 1 1 d . . . . .
F6 F 0.2428(2) 0.43094(14) 0.05304(12) 0.0646(5) Uani 1 1 d . . . . .
F7 F 0.0949(2) 0.62952(16) -0.08512(13) 0.0803(6) Uani 1 1 d . . . . .
F8 F -0.0970(2) 0.76655(15) 0.00836(17) 0.0856(6) Uani 1 1 d . . . . .
F9 F -0.13832(19) 0.70111(15) 0.24316(16) 0.0725(5) Uani 1 1 d . . . . .
F10 F 0.00803(18) 0.50617(14) 0.38191(13) 0.0595(4) Uani 1 1 d . . . . .
O1 O 0.20227(16) 0.23857(13) 0.26249(12) 0.0348(4) Uani 1 1 d . . . . .
O2 O 0.14051(16) 0.28781(13) 0.42837(12) 0.0337(3) 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 0.0033 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'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 '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
C9 B1 C15 117.74(18) . . ?
O1 B1 C9 109.5(2) . . ?
O1 B1 C15 108.09(18) . . ?
O2 B1 C9 109.20(18) . . ?
O2 B1 C15 110.09(19) . . ?
O2 B1 O1 100.90(16) . . ?
C2 C1 C7 122.08(19) . 2_556 ?
O1 C1 C2 112.08(19) . . ?
O1 C1 C7 125.8(2) . 2_556 ?
C1 C2 C3 122.3(2) . . ?
O2 C2 C1 111.89(18) . . ?
O2 C2 C3 125.8(2) . . ?
C4 C3 C2 122.5(2) . . ?
C4 C3 C8 121.15(19) . . ?
C8 C3 C2 116.4(2) . . ?
C3 C4 H4 120.3 . . ?
C5 C4 C3 119.5(2) . . ?
C5 C4 H4 120.3 . . ?
C4 C5 Br1 119.86(19) . . ?
C6 C5 Br1 118.83(17) . . ?
C6 C5 C4 121.3(2) . . ?
C5 C6 H6 120.3 . . ?
C5 C6 C7 119.4(2) . . ?
C7 C6 H6 120.3 . . ?
C6 C7 C1 122.05(19) . 2_556 ?
C6 C7 C8 121.6(2) . . ?
C8 C7 C1 116.3(2) . 2_556 ?
C3 C8 C8 121.4(2) . 2_556 ?
C7 C8 C3 117.0(2) . . ?
C7 C8 C8 121.5(2) . 2_556 ?
C10 C9 B1 125.6(2) . . ?
C14 C9 B1 120.5(2) . . ?
C14 C9 C10 113.9(2) . . ?
C11 C10 C9 123.4(2) . . ?
F1 C10 C9 120.4(2) . . ?
F1 C10 C11 116.2(2) . . ?
C12 C11 C10 119.5(2) . . ?
F2 C11 C10 120.4(2) . . ?
F2 C11 C12 120.2(2) . . ?
C11 C12 C13 120.0(2) . . ?
F3 C12 C11 119.8(2) . . ?
F3 C12 C13 120.2(3) . . ?
C12 C13 C14 119.1(2) . . ?
F4 C13 C12 120.1(2) . . ?
F4 C13 C14 120.8(2) . . ?
C9 C14 C13 124.1(2) . . ?
F5 C14 C9 119.4(2) . . ?
F5 C14 C13 116.4(2) . . ?
C16 C15 B1 120.4(2) . . ?
C20 C15 B1 124.6(2) . . ?
C20 C15 C16 114.9(2) . . ?
C17 C16 C15 123.6(3) . . ?
F6 C16 C15 119.5(2) . . ?
F6 C16 C17 116.9(2) . . ?
C18 C17 C16 119.2(3) . . ?
F7 C17 C16 120.8(3) . . ?
F7 C17 C18 120.0(3) . . ?
C19 C18 C17 119.4(2) . . ?
F8 C18 C17 120.1(3) . . ?
F8 C18 C19 120.4(3) . . ?
C18 C19 C20 119.7(3) . . ?
F9 C19 C18 120.0(2) . . ?
F9 C19 C20 120.3(3) . . ?
C15 C20 C19 123.1(2) . . ?
F10 C20 C15 121.3(2) . . ?
F10 C20 C19 115.6(2) . . ?
C1 O1 B1 107.43(17) . . ?
C2 O2 B1 107.69(18) . . ?
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
B1 C9 1.612(3) . ?
B1 C15 1.619(3) . ?
B1 O1 1.542(3) . ?
B1 O2 1.535(3) . ?
Br1 C5 1.888(2) . ?
C1 C2 1.399(3) . ?
C1 C7 1.429(3) 2_556 ?
C1 O1 1.300(2) . ?
C2 C3 1.425(3) . ?
C2 O2 1.302(3) . ?
C3 C4 1.400(3) . ?
C3 C8 1.417(3) . ?
C4 H4 0.9500 . ?
C4 C5 1.385(3) . ?
C5 C6 1.382(3) . ?
C6 H6 0.9500 . ?
C6 C7 1.394(3) . ?
C7 C8 1.416(3) . ?
C8 C8 1.439(4) 2_556 ?
C9 C10 1.391(3) . ?
C9 C14 1.378(3) . ?
C10 C11 1.381(3) . ?
C10 F1 1.336(3) . ?
C11 C12 1.360(4) . ?
C11 F2 1.341(3) . ?
C12 C13 1.361(4) . ?
C12 F3 1.352(3) . ?
C13 C14 1.381(4) . ?
C13 F4 1.342(3) . ?
C14 F5 1.351(3) . ?
C15 C16 1.380(3) . ?
C15 C20 1.375(4) . ?
C16 C17 1.376(4) . ?
C16 F6 1.354(3) . ?
C17 C18 1.375(4) . ?
C17 F7 1.339(3) . ?
C18 C19 1.361(4) . ?
C18 F8 1.339(3) . ?
C19 C20 1.385(4) . ?
C19 F9 1.343(3) . ?
C20 F10 1.344(3) . ?
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
B1 C9 C10 C11 178.2(2) . . . . ?
B1 C9 C10 F1 -1.2(4) . . . . ?
B1 C9 C14 C13 -177.4(3) . . . . ?
B1 C9 C14 F5 2.1(4) . . . . ?
B1 C15 C16 C17 179.3(2) . . . . ?
B1 C15 C16 F6 -2.4(3) . . . . ?
B1 C15 C20 C19 -178.7(2) . . . . ?
B1 C15 C20 F10 2.6(3) . . . . ?
Br1 C5 C6 C7 179.13(17) . . . . ?
C1 C2 C3 C4 -179.1(2) . . . . ?
C1 C2 C3 C8 1.0(3) . . . . ?
C1 C2 O2 B1 0.5(2) . . . . ?
C1 C7 C8 C3 179.12(19) 2_556 . . . ?
C1 C7 C8 C8 -0.8(4) 2_556 . . 2_556 ?
C2 C1 O1 B1 0.2(2) . . . . ?
C2 C3 C4 C5 -179.5(2) . . . . ?
C2 C3 C8 C7 179.13(19) . . . . ?
C2 C3 C8 C8 -1.0(4) . . . 2_556 ?
C3 C2 O2 B1 -179.9(2) . . . . ?
C3 C4 C5 Br1 -179.21(17) . . . . ?
C3 C4 C5 C6 0.0(4) . . . . ?
C4 C3 C8 C7 -0.8(3) . . . . ?
C4 C3 C8 C8 179.1(2) . . . 2_556 ?
C4 C5 C6 C7 -0.1(4) . . . . ?
C5 C6 C7 C1 -178.6(2) . . . 2_556 ?
C5 C6 C7 C8 -0.3(3) . . . . ?
C6 C7 C8 C3 0.7(3) . . . . ?
C6 C7 C8 C8 -179.2(2) . . . 2_556 ?
C7 C1 C2 C3 -0.1(3) 2_556 . . . ?
C7 C1 C2 O2 179.52(19) 2_556 . . . ?
C7 C1 O1 B1 -179.8(2) 2_556 . . . ?
C8 C3 C4 C5 0.5(3) . . . . ?
C9 B1 C15 C16 76.2(3) . . . . ?
C9 B1 C15 C20 -104.1(3) . . . . ?
C9 B1 O1 C1 115.18(19) . . . . ?
C9 B1 O2 C2 -115.7(2) . . . . ?
C9 C10 C11 C12 -0.4(4) . . . . ?
C9 C10 C11 F2 -179.7(2) . . . . ?
C10 C9 C14 C13 1.1(4) . . . . ?
C10 C9 C14 F5 -179.3(2) . . . . ?
C10 C11 C12 C13 0.2(4) . . . . ?
C10 C11 C12 F3 -179.5(3) . . . . ?
C11 C12 C13 C14 0.7(5) . . . . ?
C11 C12 C13 F4 179.4(3) . . . . ?
C12 C13 C14 C9 -1.4(5) . . . . ?
C12 C13 C14 F5 179.1(3) . . . . ?
C14 C9 C10 C11 -0.2(4) . . . . ?
C14 C9 C10 F1 -179.6(2) . . . . ?
C15 B1 C9 C10 0.0(4) . . . . ?
C15 B1 C9 C14 178.4(2) . . . . ?
C15 B1 O1 C1 -115.40(19) . . . . ?
C15 B1 O2 C2 113.6(2) . . . . ?
C15 C16 C17 C18 -0.7(4) . . . . ?
C15 C16 C17 F7 179.8(2) . . . . ?
C16 C15 C20 C19 1.1(3) . . . . ?
C16 C15 C20 F10 -177.6(2) . . . . ?
C16 C17 C18 C19 1.4(4) . . . . ?
C16 C17 C18 F8 179.7(2) . . . . ?
C17 C18 C19 C20 -0.9(4) . . . . ?
C17 C18 C19 F9 178.9(2) . . . . ?
C18 C19 C20 C15 -0.4(4) . . . . ?
C18 C19 C20 F10 178.4(2) . . . . ?
C20 C15 C16 C17 -0.5(4) . . . . ?
C20 C15 C16 F6 177.8(2) . . . . ?
F1 C10 C11 C12 179.0(2) . . . . ?
F1 C10 C11 F2 -0.2(4) . . . . ?
F2 C11 C12 C13 179.4(3) . . . . ?
F2 C11 C12 F3 -0.2(4) . . . . ?
F3 C12 C13 C14 -179.7(3) . . . . ?
F3 C12 C13 F4 -1.0(5) . . . . ?
F4 C13 C14 C9 179.9(3) . . . . ?
F4 C13 C14 F5 0.3(4) . . . . ?
F6 C16 C17 C18 -179.0(2) . . . . ?
F6 C16 C17 F7 1.4(4) . . . . ?
F7 C17 C18 C19 -179.0(2) . . . . ?
F7 C17 C18 F8 -0.8(4) . . . . ?
F8 C18 C19 C20 -179.2(2) . . . . ?
F8 C18 C19 F9 0.6(4) . . . . ?
F9 C19 C20 C15 179.8(2) . . . . ?
F9 C19 C20 F10 -1.5(3) . . . . ?
O1 B1 C9 C10 124.0(2) . . . . ?
O1 B1 C9 C14 -57.7(3) . . . . ?
O1 B1 C15 C16 -48.5(3) . . . . ?
O1 B1 C15 C20 131.3(2) . . . . ?
O1 B1 O2 C2 -0.4(2) . . . . ?
O1 C1 C2 C3 179.95(19) . . . . ?
O1 C1 C2 O2 -0.5(3) . . . . ?
O2 B1 C9 C10 -126.4(2) . . . . ?
O2 B1 C9 C14 52.0(3) . . . . ?
O2 B1 C15 C16 -157.8(2) . . . . ?
O2 B1 C15 C20 21.9(3) . . . . ?
O2 B1 O1 C1 0.1(2) . . . . ?
O2 C2 C3 C4 1.4(4) . . . . ?
O2 C2 C3 C8 -178.6(2) . . . . ?
