#------------------------------------------------------------------------------
#$Date: 2021-09-06 12:08:56 +0300 (Mon, 06 Sep 2021) $
#$Revision: 268527 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/12/86/7128645.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_7128645
loop_
_publ_author_name
'Liao, Guanming'
'Zhang, Jia'
'Zheng, Xiaoyan'
'Jia, Xiaodi'
'Xu, Jialiang'
'Zhao, Fenggui'
'Wang, Nan'
'Liu, Kanglei'
'Chen, Pangkuan'
'Yin, Xiaodong'
_publ_section_title
;
 Crystallization-induced emission enhancement of highly electron-deficient
 dicyanomethylene-bridged triarylboranes.
;
_journal_issue                   64
_journal_name_full
'Chemical communications (Cambridge, England)'
_journal_page_first              7926
_journal_page_last               7929
_journal_paper_doi               10.1039/d1cc03311e
_journal_volume                  57
_journal_year                    2021
_chemical_formula_moiety         'C29 H12 B F9 N2'
_chemical_formula_sum            'C29 H12 B F9 N2'
_chemical_formula_weight         570.22
_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_date             2021-05-27
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2021-05-31 deposited with the CCDC.	2021-07-13 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 91.096(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.0142(3)
_cell_length_b                   17.7383(6)
_cell_length_c                   20.3579(6)
_cell_measurement_reflns_used    2405
_cell_measurement_temperature    299.99(13)
_cell_measurement_theta_max      74.3910
_cell_measurement_theta_min      4.3230
_cell_volume                     2532.47(16)
_computing_cell_refinement       'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      299.99(13)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.966
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -26.00  13.00   1.00    5.00    --    0.00 -82.00-150.00   39
  2  ω    -89.00 -37.00   1.00    5.00    --    0.00 -19.00-150.00   52
  3  ω    -38.00  34.00   1.00    5.00    --    0.00 -82.00  90.00   72
  4  ω     19.00  54.00   1.00   40.00    --  101.30 -38.00-120.00   35
  5  ω     22.00 101.00   1.00   40.00    --  101.30 -38.00   0.00   79
  6  ω     22.00 123.00   1.00   40.00    --  101.30 -38.00 120.00  101
  7  ω    137.00 168.00   1.00   40.00    --  101.30  57.00  30.00   31
  8  ω     75.00 123.00   1.00   40.00    --  101.30  57.00  30.00   48
  9  ω     15.00  40.00   1.00   40.00    --  101.30 -19.00  90.00   25
 10  ω     52.00 134.00   1.00   40.00    --  101.30 -19.00  90.00   82
 11  ω     59.00  86.00   1.00   40.00    --  101.30 -38.00-120.00   27
 12  ω    118.00 191.00   1.00   40.00    --  101.30  82.00-180.00   73
 13  ω     69.00 128.00   1.00   40.00    --  101.30  19.00   0.00   59
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC12 (RINC): Kappa single'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1617692000
_diffrn_orient_matrix_UB_12      0.0549918000
_diffrn_orient_matrix_UB_13      0.0170702000
_diffrn_orient_matrix_UB_21      0.0988086000
_diffrn_orient_matrix_UB_22      0.0167965000
_diffrn_orient_matrix_UB_23      0.0666556000
_diffrn_orient_matrix_UB_31      0.1110746000
_diffrn_orient_matrix_UB_32      0.0650497000
_diffrn_orient_matrix_UB_33      -0.0315714000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0423
_diffrn_reflns_av_unetI/netI     0.0496
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.966
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            13805
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.966
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.287
_diffrn_reflns_theta_min         4.344
_diffrn_source                   'Rotating-anode X-ray tube (dual wavelength)'
_diffrn_source_type              'Rigaku (Cu) X-ray DW Source'
_exptl_absorpt_coefficient_mu    1.182
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.80735
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.84a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_density_diffrn    1.496
_exptl_crystal_description       block
_exptl_crystal_F_000             1144
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.276
_refine_diff_density_min         -0.244
_refine_diff_density_rms         0.050
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     398
_refine_ls_number_reflns         5124
_refine_ls_number_restraints     93
_refine_ls_restrained_S_all      1.100
_refine_ls_R_factor_all          0.1004
_refine_ls_R_factor_gt           0.0548
_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)+(0.0682P)²+0.8994P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1293
_refine_ls_wR_factor_ref         0.1608
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3066
_reflns_number_total             5124
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d1cc03311e2.cif
_cod_data_source_block           4-fbcn
_cod_depositor_comments
'Adding full bibliography for 7128644--7128650.cif.'
_cod_database_code               7128645
_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.
;
_reflns_odcompleteness_completeness 99.89
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Others
 Fixed Uiso: H10(0.058) H5(0.056) H6(0.062) H9(0.066) H11(0.067) H7(0.067)
 H12(0.066) H8(0.071) H1(0.068) H4(0.071) H2(0.081) H3(0.084)
 Fixed X: H10(0.383803) H5(0.331533) H6(0.236444) H9(0.261189) H11(0.793711)
 H7(0.154686) H12(0.333666) H8(0.165094) H1(0.801679) H4(0.70269) H2(0.984478)
 H3(0.940022)
 Fixed Y: H10(0.310852) H5(0.425301) H6(0.545635) H9(0.426618) H11(0.135787)
 H7(0.609174) H12(0.025032) H8(0.549565) H1(0.108565) H4(0.239997) H2(0.082796)
 H3(0.150675)
 Fixed Z: H10(0.421889) H5(0.625463) H6(0.570303) H9(0.367367) H11(0.317434)
 H7(0.47633) H12(0.377944) H8(0.374952) H1(0.539472) H4(0.73155) H2(0.631746)
 H3(0.726993)
;
_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
;
_oxdiff_exptl_absorpt_empirical_full_max 1.508
_oxdiff_exptl_absorpt_empirical_full_min 0.745
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
F4 F 0.2215(3) 0.15005(11) 0.52450(10) 0.0908(7) Uani 1 1 d . . . . .
F1 F 0.8672(3) 0.26142(12) 0.46680(9) 0.0890(7) Uani 1 1 d . . . . .
F5 F 0.1017(3) 0.07064(15) 0.45804(11) 0.1025(8) Uani 1 1 d . . . . .
F3 F 0.9963(3) 0.22053(14) 0.38118(13) 0.1092(9) Uani 1 1 d . . . . .
F6 F 0.3103(4) 0.03674(14) 0.52563(12) 0.1149(9) Uani 1 1 d . . . . .
F2 F 0.7744(4) 0.30035(13) 0.37413(13) 0.1138(9) Uani 1 1 d . . . . .
C8 C 0.4080(4) 0.32985(14) 0.58085(11) 0.0448(6) Uani 1 1 d . . . . .
C17 C 0.4340(4) 0.29464(14) 0.51796(11) 0.0447(6) Uani 1 1 d . . . . .
C10 C 0.2977(4) 0.44474(15) 0.52745(12) 0.0454(6) Uani 1 1 d . . . . .
C21 C 0.5454(4) 0.16875(14) 0.44918(12) 0.0453(6) Uani 1 1 d . . . . .
C16 C 0.3767(4) 0.33442(15) 0.46258(12) 0.0483(6) Uani 1 1 d . . . . .
H10 H 0.383803 0.310852 0.421889 0.058 Uiso 1 1 calc R . . . .
C9 C 0.3443(4) 0.40289(15) 0.58448(12) 0.0468(6) Uani 1 1 d . . . . .
H5 H 0.331533 0.425301 0.625463 0.056 Uiso 1 1 calc R . . . .
C7 C 0.4491(4) 0.28432(15) 0.64000(12) 0.0463(6) Uani 1 1 d . . . . .
C22 C 0.6867(4) 0.17712(15) 0.40144(12) 0.0483(6) Uani 1 1 d . . . . .
C26 C 0.4155(4) 0.10979(14) 0.43798(13) 0.0477(6) Uani 1 1 d . . . . .
C15 C 0.3081(4) 0.40899(15) 0.46497(12) 0.0464(6) Uani 1 1 d . . . . .
C6 C 0.6084(4) 0.22906(15) 0.63769(12) 0.0485(6) Uani 1 1 d . . . . .
C1 C 0.6408(4) 0.19156(15) 0.57785(12) 0.0483(6) Uani 1 1 d . . . . .
C11 C 0.2409(4) 0.52108(15) 0.53000(14) 0.0513(7) Uani 1 1 d . . . . .
H6 H 0.236444 0.545635 0.570303 0.062 Uiso 1 1 calc R . . . .
C18 C 0.3349(4) 0.28727(16) 0.69356(12) 0.0535(7) Uani 1 1 d . . . . .
C14 C 0.2565(4) 0.44975(16) 0.40830(13) 0.0554(7) Uani 1 1 d . . . . .
H9 H 0.261189 0.426618 0.367367 0.066 Uiso 1 1 calc R . . . .
C23 C 0.6978(4) 0.12905(16) 0.34780(13) 0.0562(7) Uani 1 1 d . . . . .
H11 H 0.793711 0.135787 0.317434 0.067 Uiso 1 1 calc R . . . .
C12 C 0.1926(4) 0.55902(16) 0.47395(15) 0.0560(7) Uani 1 1 d . . . . .
H7 H 0.154686 0.609174 0.476330 0.067 Uiso 1 1 calc R . . . .
C25 C 0.4245(5) 0.06270(16) 0.38401(13) 0.0553(7) Uani 1 1 d . . . . .
H12 H 0.333666 0.025032 0.377944 0.066 Uiso 1 1 calc R . . . .
F9 F 0.5930(9) 0.0558(3) 0.22631(15) 0.0952(18) Uani 0.656(9) 1 d D U P A 1
C24 C 0.5676(5) 0.07135(16) 0.33916(13) 0.0577(7) Uani 1 1 d D U . . .
C13 C 0.1996(4) 0.52318(17) 0.41283(15) 0.0588(7) Uani 1 1 d . . . . .
H8 H 0.165094 0.549565 0.374952 0.071 Uiso 1 1 calc R . . . .
C27 C 0.8303(5) 0.23894(17) 0.40582(14) 0.0594(8) Uani 1 1 d . . . . .
C2 C 0.7816(4) 0.13581(16) 0.57775(14) 0.0569(7) Uani 1 1 d . . . . .
H1 H 0.801679 0.108565 0.539472 0.068 Uiso 1 1 calc R . . . .
C28 C 0.2633(4) 0.09294(17) 0.48610(15) 0.0576(7) Uani 1 1 d . . . . .
C5 C 0.7221(4) 0.21376(18) 0.69270(14) 0.0590(7) Uani 1 1 d . . . . .
H4 H 0.702690 0.239997 0.731550 0.071 Uiso 1 1 calc R . . . .
C20 C 0.3545(5) 0.23811(19) 0.74926(14) 0.0636(8) Uani 1 1 d . . . . .
C19 C 0.1706(5) 0.33468(18) 0.69927(14) 0.0643(8) Uani 1 1 d . . . . .
N2 N 0.3550(5) 0.2007(2) 0.79458(14) 0.0945(11) Uani 1 1 d . . . . .
N1 N 0.0367(5) 0.3682(2) 0.70987(16) 0.0983(11) Uani 1 1 d . . . . .
C3 C 0.8916(5) 0.1202(2) 0.63302(16) 0.0678(9) Uani 1 1 d . . . . .
H2 H 0.984478 0.082796 0.631746 0.081 Uiso 1 1 calc R . . . .
C4 C 0.8634(5) 0.1601(2) 0.69012(16) 0.0701(9) Uani 1 1 d . . . . .
H3 H 0.940022 0.150675 0.726993 0.084 Uiso 1 1 calc R . . . .
B1 B 0.5356(4) 0.21835(17) 0.51468(14) 0.0467(7) Uani 1 1 d . . . . .
C29 C 0.5849(6) 0.0180(2) 0.28353(17) 0.0781(10) Uani 1 1 d D U . . .
F8 F 0.7441(12) -0.0175(5) 0.2834(3) 0.155(4) Uani 0.656(9) 1 d D U P A 1
F7 F 0.4419(15) -0.0263(6) 0.2752(5) 0.187(5) Uani 0.656(9) 1 d D U P A 1
F8A F 0.743(2) 0.0173(9) 0.2549(9) 0.183(9) Uani 0.344(9) 1 d D U P A 2
F9A F 0.435(2) 0.0151(9) 0.2469(8) 0.164(8) Uani 0.344(9) 1 d D U P A 2
F7A F 0.588(2) -0.0535(4) 0.3086(5) 0.104(4) Uani 0.344(9) 1 d D U P A 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'
B B 0.0090 0.0039 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 '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'
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
C17 C8 C7 117.6(2) . . ?
C9 C8 C17 120.3(2) . . ?
C9 C8 C7 122.1(2) . . ?
C8 C17 B1 119.3(2) . . ?
C16 C17 C8 117.6(2) . . ?
C16 C17 B1 122.9(2) . . ?
C9 C10 C15 119.1(2) . . ?
C9 C10 C11 122.3(2) . . ?
C11 C10 C15 118.6(2) . . ?
C22 C21 B1 124.0(2) . . ?
C26 C21 C22 115.4(2) . . ?
C26 C21 B1 120.5(2) . . ?
C17 C16 C15 123.0(2) . . ?
C8 C9 C10 121.5(2) . . ?
C8 C7 C6 118.1(2) . . ?
C18 C7 C8 121.5(2) . . ?
C18 C7 C6 120.2(2) . . ?
C21 C22 C27 121.3(2) . . ?
C23 C22 C21 121.9(3) . . ?
C23 C22 C27 116.8(2) . . ?
C21 C26 C28 120.9(2) . . ?
C25 C26 C21 122.7(2) . . ?
C25 C26 C28 116.4(2) . . ?
C16 C15 C10 118.2(2) . . ?
C14 C15 C10 119.2(2) . . ?
C14 C15 C16 122.6(2) . . ?
C1 C6 C7 118.2(2) . . ?
C5 C6 C7 121.6(2) . . ?
C5 C6 C1 120.3(3) . . ?
C6 C1 B1 119.4(2) . . ?
C2 C1 C6 117.4(3) . . ?
C2 C1 B1 122.9(2) . . ?
C12 C11 C10 120.6(3) . . ?
C7 C18 C20 124.0(3) . . ?
C7 C18 C19 124.9(3) . . ?
C19 C18 C20 110.9(2) . . ?
C13 C14 C15 120.5(3) . . ?
C24 C23 C22 120.6(2) . . ?
C11 C12 C13 120.5(3) . . ?
C24 C25 C26 120.3(3) . . ?
C23 C24 C29 120.4(3) . . ?
C25 C24 C23 119.1(2) . . ?
C25 C24 C29 120.4(3) . . ?
C14 C13 C12 120.6(3) . . ?
F1 C27 C22 113.4(2) . . ?
F3 C27 F1 105.8(3) . . ?
F3 C27 F2 105.9(3) . . ?
F3 C27 C22 113.3(2) . . ?
F2 C27 F1 105.1(3) . . ?
F2 C27 C22 112.5(3) . . ?
C3 C2 C1 121.7(3) . . ?
F4 C28 F5 106.8(3) . . ?
F4 C28 F6 106.0(3) . . ?
F4 C28 C26 113.9(2) . . ?
F5 C28 C26 113.3(3) . . ?
F6 C28 F5 103.9(3) . . ?
F6 C28 C26 112.2(3) . . ?
C4 C5 C6 120.5(3) . . ?
N2 C20 C18 174.4(4) . . ?
N1 C19 C18 172.6(3) . . ?
C4 C3 C2 119.8(3) . . ?
C5 C4 C3 120.2(3) . . ?
C17 B1 C21 123.3(2) . . ?
C17 B1 C1 116.8(2) . . ?
C1 B1 C21 119.8(2) . . ?
F9 C29 C24 110.5(3) . . ?
F8 C29 F9 101.0(4) . . ?
F8 C29 C24 113.6(4) . . ?
F8 C29 F7 112.1(6) . . ?
F7 C29 F9 103.6(6) . . ?
F7 C29 C24 114.6(4) . . ?
F8A C29 C24 116.5(6) . . ?
F8A C29 F9A 116.6(10) . . ?
F8A C29 F7A 99.0(9) . . ?
F9A C29 C24 113.2(8) . . ?
F9A C29 F7A 100.7(8) . . ?
F7A C29 C24 107.9(4) . . ?
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
F4 C28 1.316(3) . ?
F1 C27 1.325(3) . ?
F5 C28 1.320(4) . ?
F3 C27 1.318(4) . ?
F6 C28 1.319(4) . ?
F2 C27 1.322(4) . ?
C8 C17 1.439(3) . ?
C8 C9 1.373(4) . ?
C8 C7 1.474(4) . ?
C17 C16 1.383(4) . ?
C17 B1 1.531(4) . ?
C10 C9 1.411(4) . ?
C10 C15 1.424(3) . ?
C10 C11 1.413(4) . ?
C21 C22 1.409(3) . ?
C21 C26 1.403(4) . ?
C21 B1 1.600(4) . ?
C16 C15 1.409(4) . ?
C7 C6 1.487(4) . ?
C7 C18 1.366(3) . ?
C22 C23 1.389(4) . ?
C22 C27 1.490(4) . ?
C26 C25 1.383(4) . ?
C26 C28 1.493(4) . ?
C15 C14 1.403(4) . ?
C6 C1 1.410(4) . ?
C6 C5 1.389(4) . ?
C1 C2 1.397(4) . ?
C1 B1 1.545(4) . ?
C11 C12 1.362(4) . ?
C18 C20 1.435(4) . ?
C18 C19 1.433(4) . ?
C14 C13 1.366(4) . ?
C23 C24 1.381(4) . ?
C12 C13 1.399(4) . ?
C25 C24 1.378(4) . ?
F9 C29 1.346(5) . ?
C24 C29 1.482(4) . ?
C2 C3 1.380(4) . ?
C5 C4 1.376(4) . ?
C20 N2 1.136(4) . ?
C19 N1 1.135(4) . ?
C3 C4 1.378(5) . ?
C29 F8 1.283(6) . ?
C29 F7 1.283(6) . ?
C29 F8A 1.261(9) . ?
C29 F9A 1.277(10) . ?
C29 F7A 1.368(8) . ?
