#------------------------------------------------------------------------------
#$Date: 2021-09-06 11:08:56 +0200 (Mon 06 de Sep de 2021) $
#$Revision: 268527 $
#$URL: svn://www.crystallography.net/cod/cif/7/12/86/7128644.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_7128644
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
_atom_sites_solution_primary     dual
_audit_creation_date             2020-05-01
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2020-07-02 deposited with the CCDC.	2021-07-13 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 91.795(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.8971(3)
_cell_length_b                   17.6628(7)
_cell_length_c                   20.2921(8)
_cell_measurement_reflns_used    8497
_cell_measurement_temperature    180(2)
_cell_measurement_theta_max      26.50
_cell_measurement_theta_min      2.31
_cell_volume                     2470.81(18)
_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 (Sheldrick, 2015)'
_diffrn_ambient_temperature      180.0
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.997
_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  0.0486
_diffrn_reflns_av_unetI/netI     0.0415
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            31599
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.575
_diffrn_reflns_theta_min         2.306
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.138
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6350
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0887 before and 0.0539 after correction. The Ratio of minimum to maximum transmission is 0.8517. The λ/2 correction factor is Not present.'
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.533
_exptl_crystal_description       block
_exptl_crystal_F_000             1144
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.13
_refine_diff_density_max         0.248
_refine_diff_density_min         -0.269
_refine_diff_density_rms         0.049
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     398
_refine_ls_number_reflns         5681
_refine_ls_number_restraints     93
_refine_ls_restrained_S_all      1.122
_refine_ls_R_factor_all          0.0769
_refine_ls_R_factor_gt           0.0441
_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)+(0.0544P)²+0.7085P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1022
_refine_ls_wR_factor_ref         0.1172
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3926
_reflns_number_total             5681
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d1cc03311e2.cif
_cod_data_source_block           mo_191030_wsn_lgm_4fbcn_0m
_cod_depositor_comments
'Adding full bibliography for 7128644--7128650.cif.'
_cod_database_code               7128644
_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   0.982
_shelx_estimated_absorpt_t_min   0.966
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2. Restrained distances
 F8-F9 \\sim F9-F7
 with sigma of 0.04
 C29-F8 \\sim C29-F9 \\sim C29-F7 \\sim C29-C24
 with sigma of 0.02
 F9-F8 \\sim F9-F7 \\sim F8-F7 \\sim F8A-F7A \\sim F8A-F9A \\sim F7A-F9A
 with sigma of 0.04
 C29-F9 \\sim C29-C24 \\sim C29-F8 \\sim C29-F7 \\sim C29-F8A \\sim C29-F7A
\\sim C29-F9A
 with sigma of 0.02
 F8A-F7A \\sim F9A-F7A
 with sigma of 0.04
 C29-F8A \\sim C29-F7 \\sim C29-F9A \\sim C29-F8 \\sim C29-F9 \\sim C29-F7A
\\sim C29-C24
 with sigma of 0.02
3. Rigid body (RIGU) restrains
 F9, F8, F7, C29, C24
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 F8A, F7A, F9A, C29, C24
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
4. Others
 Sof(F8A)=Sof(F7A)=Sof(F9A)=1-FVAR(1)
 Sof(F9)=Sof(F8)=Sof(F7)=FVAR(1)
5.a Aromatic/amide H refined with riding coordinates:
 C9(H9), C16(H16), C11(H11), C14(H14), C12(H12), C25(H25), C2(H2), C5(H5),
 C13(H13), C23(H23), C4(H4), C3(H3)
;
_olex2_submission_original_sample_id 4FBCN_BIT
_olex2_submission_special_instructions 'No special instructions were received'
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
F1 F 0.21632(16) 0.84980(6) 0.52344(6) 0.0452(3) Uani 1 1 d . . . . .
F4 F 0.87414(17) 0.74076(7) 0.46931(5) 0.0456(3) Uani 1 1 d . . . . .
F2 F 0.09219(15) 0.93040(7) 0.45574(6) 0.0517(3) Uani 1 1 d . . . . .
F5 F 1.00581(16) 0.78097(7) 0.38274(6) 0.0557(4) Uani 1 1 d . . . . .
F3 F 0.31018(18) 0.96452(7) 0.52561(6) 0.0557(4) Uani 1 1 d . . . . .
F6 F 0.77942(19) 0.69894(7) 0.37541(7) 0.0597(4) Uani 1 1 d . . . . .
F9 F 0.5889(4) 0.94272(14) 0.22439(9) 0.0577(8) Uani 0.700(5) 1 d D U P A 1
C17 C 0.4354(2) 0.70569(9) 0.51829(8) 0.0226(3) Uani 1 1 d . . . . .
C10 C 0.2977(2) 0.55493(9) 0.52829(8) 0.0227(3) Uani 1 1 d . . . . .
C8 C 0.4093(2) 0.67076(9) 0.58175(8) 0.0226(3) Uani 1 1 d . . . . .
C21 C 0.5453(2) 0.83198(9) 0.44887(8) 0.0229(3) Uani 1 1 d . . . . .
C9 C 0.3446(2) 0.59739(9) 0.58547(8) 0.0237(3) Uani 1 1 d . . . . .
H9 H 0.331186 0.574702 0.627530 0.028 Uiso 1 1 calc R . . . .
C26 C 0.6884(2) 0.82349(9) 0.40154(8) 0.0250(4) Uani 1 1 d . . . . .
C16 C 0.3776(2) 0.66555(9) 0.46272(8) 0.0241(3) Uani 1 1 d . . . . .
H16 H 0.385192 0.689377 0.420911 0.029 Uiso 1 1 calc R . . . .
C15 C 0.3076(2) 0.59046(9) 0.46548(8) 0.0235(3) Uani 1 1 d . . . . .
C6 C 0.6114(2) 0.77290(9) 0.63877(8) 0.0246(4) Uani 1 1 d . . . . .
C22 C 0.4114(2) 0.89056(9) 0.43667(8) 0.0247(4) Uani 1 1 d . . . . .
C11 C 0.2403(2) 0.47808(9) 0.53124(8) 0.0264(4) Uani 1 1 d . . . . .
H11 H 0.235493 0.453212 0.572664 0.032 Uiso 1 1 calc R . . . .
C7 C 0.4512(2) 0.71687(9) 0.64085(8) 0.0239(3) Uani 1 1 d . . . . .
C1 C 0.6422(2) 0.81106(9) 0.57867(8) 0.0249(4) Uani 1 1 d . . . . .
C14 C 0.2557(2) 0.54881(10) 0.40820(8) 0.0286(4) Uani 1 1 d . . . . .
H14 H 0.260969 0.572129 0.366104 0.034 Uiso 1 1 calc R . . . .
N1 N 0.0364(3) 0.63111(11) 0.71232(9) 0.0552(5) Uani 1 1 d . . . . .
C12 C 0.1918(2) 0.43962(9) 0.47480(9) 0.0294(4) Uani 1 1 d . . . . .
H12 H 0.153385 0.388071 0.477336 0.035 Uiso 1 1 calc R . . . .
C18 C 0.3374(2) 0.71373(10) 0.69462(8) 0.0276(4) Uani 1 1 d . . . . .
N2 N 0.3587(3) 0.80286(11) 0.79528(8) 0.0505(5) Uani 1 1 d . . . . .
C25 C 0.6997(2) 0.87093(9) 0.34719(8) 0.0292(4) Uani 1 1 d . . . . .
H25 H 0.799603 0.864011 0.316578 0.035 Uiso 1 1 calc R . . . .
C2 C 0.7847(2) 0.86751(10) 0.57861(9) 0.0306(4) Uani 1 1 d . . . . .
H2 H 0.803885 0.895470 0.539357 0.037 Uiso 1 1 calc R . . . .
C5 C 0.7287(3) 0.78843(10) 0.69399(9) 0.0315(4) Uani 1 1 d . . . . .
H5 H 0.710237 0.761367 0.733765 0.038 Uiso 1 1 calc R . . . .
C13 C 0.1978(2) 0.47514(10) 0.41312(9) 0.0310(4) Uani 1 1 d . . . . .
H13 H 0.161398 0.447719 0.374403 0.037 Uiso 1 1 calc R . . . .
C28 C 0.8365(3) 0.76159(10) 0.40708(9) 0.0311(4) Uani 1 1 d . . . . .
C23 C 0.4196(3) 0.93756(10) 0.38228(8) 0.0295(4) Uani 1 1 d . . . . .
H23 H 0.325161 0.976181 0.375578 0.035 Uiso 1 1 calc R . . . .
C19 C 0.1715(3) 0.66571(11) 0.70095(9) 0.0348(4) Uani 1 1 d . . . . .
C27 C 0.2581(2) 0.90808(10) 0.48504(9) 0.0294(4) Uani 1 1 d . . . . .
C4 C 0.8725(3) 0.84308(11) 0.69156(9) 0.0361(4) Uani 1 1 d . . . . .
H4 H 0.953553 0.852732 0.729332 0.043 Uiso 1 1 calc R . . . .
C24 C 0.5650(3) 0.92830(10) 0.33776(8) 0.0315(4) Uani 1 1 d D U . . .
C3 C 0.8979(3) 0.88357(11) 0.63415(9) 0.0346(4) Uani 1 1 d . . . . .
H3 H 0.993092 0.922371 0.632938 0.042 Uiso 1 1 calc R . . . .
C20 C 0.3576(3) 0.76410(11) 0.75002(9) 0.0325(4) Uani 1 1 d . . . . .
F8 F 0.7469(6) 1.0175(2) 0.28138(15) 0.0950(18) Uani 0.700(5) 1 d D U P A 1
C29 C 0.5815(3) 0.98137(12) 0.28086(10) 0.0456(5) Uani 1 1 d D U . . .
F7 F 0.4387(8) 1.0265(3) 0.2729(2) 0.140(3) Uani 0.700(5) 1 d D U P A 1
B1 B 0.5357(3) 0.78297(10) 0.51486(9) 0.0237(4) Uani 1 1 d . . . . .
F8A F 0.720(2) 0.9765(8) 0.2470(8) 0.239(9) Uani 0.300(5) 1 d D U P A 2
F7A F 0.5997(15) 1.0530(3) 0.3061(3) 0.078(2) Uani 0.300(5) 1 d D U P A 2
F9A F 0.4192(14) 0.9927(6) 0.2503(5) 0.124(5) Uani 0.300(5) 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 0.0033 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'
F F 0.0171 0.0103 '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
_geom_angle_publ_flag
C8 C17 B1 119.33(14) . . ?
C16 C17 C8 117.92(14) . . ?
C16 C17 B1 122.64(14) . . ?
C9 C10 C15 119.05(14) . . ?
C9 C10 C11 122.16(15) . . ?
C11 C10 C15 118.79(15) . . ?
C17 C8 C7 117.63(14) . . ?
C9 C8 C17 120.12(15) . . ?
C9 C8 C7 122.24(14) . . ?
C26 C21 B1 124.25(14) . . ?
C22 C21 C26 115.46(14) . . ?
C22 C21 B1 120.20(14) . . ?
C8 C9 C10 121.53(15) . . ?
C21 C26 C28 121.19(14) . . ?
C25 C26 C21 122.39(15) . . ?
C25 C26 C28 116.41(14) . . ?
C17 C16 C15 122.69(15) . . ?
C16 C15 C10 118.36(14) . . ?
C14 C15 C10 119.27(15) . . ?
C14 C15 C16 122.31(15) . . ?
C1 C6 C7 118.30(15) . . ?
C5 C6 C7 121.59(15) . . ?
C5 C6 C1 120.11(15) . . ?
C21 C22 C27 120.73(14) . . ?
C23 C22 C21 122.68(15) . . ?
C23 C22 C27 116.49(15) . . ?
C12 C11 C10 120.24(16) . . ?
C8 C7 C6 118.24(14) . . ?
C18 C7 C8 121.74(15) . . ?
C18 C7 C6 119.79(15) . . ?
C6 C1 B1 119.15(14) . . ?
C2 C1 C6 117.68(16) . . ?
C2 C1 B1 122.78(15) . . ?
C13 C14 C15 120.22(16) . . ?
C11 C12 C13 120.88(15) . . ?
C7 C18 C19 125.19(16) . . ?
C7 C18 C20 123.78(16) . . ?
C19 C18 C20 110.76(14) . . ?
C24 C25 C26 119.82(15) . . ?
C3 C2 C1 121.65(17) . . ?
C4 C5 C6 120.54(17) . . ?
C14 C13 C12 120.57(16) . . ?
F4 C28 C26 112.63(14) . . ?
F5 C28 F4 106.02(15) . . ?
F5 C28 F6 106.53(14) . . ?
F5 C28 C26 112.94(14) . . ?
F6 C28 F4 105.88(14) . . ?
F6 C28 C26 112.31(15) . . ?
C24 C23 C22 119.97(16) . . ?
N1 C19 C18 172.69(19) . . ?
F1 C27 F2 106.99(14) . . ?
F1 C27 F3 106.02(14) . . ?
F1 C27 C22 113.26(14) . . ?
F2 C27 F3 105.37(14) . . ?
F2 C27 C22 112.52(14) . . ?
F3 C27 C22 112.11(14) . . ?
C3 C4 C5 120.00(17) . . ?
C25 C24 C29 119.93(16) . . ?
C23 C24 C25 119.64(16) . . ?
C23 C24 C29 120.40(16) . . ?
C2 C3 C4 119.88(16) . . ?
N2 C20 C18 174.52(19) . . ?
F9 C29 C24 110.37(18) . . ?
F8 C29 F9 101.5(2) . . ?
F8 C29 C24 112.8(2) . . ?
F7 C29 F9 105.1(3) . . ?
F7 C29 C24 114.4(2) . . ?
F7 C29 F8 111.5(3) . . ?
F8A C29 C24 118.7(4) . . ?
F8A C29 F7A 102.4(8) . . ?
F8A C29 F9A 115.9(9) . . ?
F7A C29 C24 107.4(3) . . ?
F9A C29 C24 112.7(5) . . ?
F9A C29 F7A 96.0(5) . . ?
C17 B1 C21 123.45(15) . . ?
C17 B1 C1 116.73(14) . . ?
C1 B1 C21 119.71(14) . . ?
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
F1 C27 1.328(2) . ?
F4 C28 1.333(2) . ?
F2 C27 1.332(2) . ?
F5 C28 1.327(2) . ?
F3 C27 1.335(2) . ?
F6 C28 1.333(2) . ?
F9 C29 1.336(3) . ?
C17 C8 1.444(2) . ?
C17 C16 1.380(2) . ?
C17 B1 1.533(2) . ?
C10 C9 1.411(2) . ?
C10 C15 1.424(2) . ?
C10 C11 1.416(2) . ?
C8 C9 1.374(2) . ?
C8 C7 1.471(2) . ?
C21 C26 1.407(2) . ?
C21 C22 1.404(2) . ?
C21 B1 1.598(2) . ?
C26 C25 1.389(2) . ?
C26 C28 1.498(2) . ?
C16 C15 1.413(2) . ?
C15 C14 1.412(2) . ?
C6 C7 1.485(2) . ?
C6 C1 1.415(2) . ?
C6 C5 1.389(2) . ?
C22 C23 1.384(2) . ?
C22 C27 1.498(2) . ?
C11 C12 1.364(2) . ?
C7 C18 1.365(2) . ?
C1 C2 1.400(2) . ?
C1 B1 1.550(3) . ?
C14 C13 1.366(2) . ?
N1 C19 1.143(2) . ?
C12 C13 1.402(2) . ?
C18 C19 1.434(2) . ?
C18 C20 1.437(2) . ?
N2 C20 1.145(2) . ?
C25 C24 1.384(2) . ?
C2 C3 1.380(3) . ?
C5 C4 1.386(3) . ?
C23 C24 1.380(2) . ?
C4 C3 1.383(3) . ?
C24 C29 1.494(2) . ?
F8 C29 1.307(3) . ?
C29 F7 1.274(4) . ?
C29 F8A 1.199(6) . ?
C29 F7A 1.369(6) . ?
C29 F9A 1.278(7) . ?
