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#$Date: 2025-08-19 00:06:14 +0300 (Tue, 19 Aug 2025) $
#$Revision: 301780 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/55/19/1551908.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_1551908
loop_
_publ_author_name
'Hai Qian'
'Morgan E. Cousins'
'Erik H. Horak'
'Audrey Wakefield'
'Matthew D. Liptak'
'Ivan Aprahamian'
_publ_section_title
;
 Suppression of Kasha's rule as a mechanism for fluorescent molecular
 rotors and aggregation-induced emission
;
_journal_name_full               'Nature Chemistry'
_journal_page_first              83
_journal_page_last               87
_journal_paper_doi               10.1038/nchem.2612
_journal_volume                  9
_journal_year                    2017
_chemical_formula_moiety         'C15 H13 B F2 N4'
_chemical_formula_sum            'C15 H13 B F2 N4'
_chemical_formula_weight         298.10
_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     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90.00
_cell_angle_beta                 114.796(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   13.747(2)
_cell_length_b                   8.8403(13)
_cell_length_c                   12.9567(18)
_cell_measurement_reflns_used    3002
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      24.086
_cell_measurement_theta_min      2.824
_cell_volume                     1429.4(4)
_computing_cell_refinement       'APEX2 (BRUKER, V2012.10-0, 2012)'
_computing_data_collection       'COSMO (BRUKER, V1.61, 2009)'
_computing_data_reduction        'SAINT v8.27A (Bruker, 2012)'
_computing_molecular_graphics
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement
;
XL, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution
;
XS, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_diffrn_ambient_temperature      173.15
_diffrn_detector_area_resol_mean 836.6
_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_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0474
_diffrn_reflns_av_unetI/netI     0.0410
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            11412
_diffrn_reflns_theta_full        25.37
_diffrn_reflns_theta_max         25.37
_diffrn_reflns_theta_min         1.63
_diffrn_source                   'fine-focus sealed tube'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.103
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_correction_T_min  0.6636
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2012/1 (Bruker,2012) was used for absorption correction.
wR2(int) was 0.0585 before and 0.0508 after correction.
The Ratio of minimum to maximum transmission is 0.8905.
The λ/2 correction factor is 0.0015.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.385
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       chunk
_exptl_crystal_F_000             616
_exptl_crystal_size_max          0.256
_exptl_crystal_size_mid          0.237
_exptl_crystal_size_min          0.115
_refine_diff_density_max         0.277
_refine_diff_density_min         -0.225
_refine_diff_density_rms         0.045
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     201
_refine_ls_number_reflns         2619
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.050
_refine_ls_R_factor_all          0.0870
_refine_ls_R_factor_gt           0.0496
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0858P)²+0.1639P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1372
_refine_ls_wR_factor_ref         0.1648
_reflns_number_gt                1646
_reflns_number_total             2619
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            nchem.2612-s2.cif
_cod_data_source_block           ia813d
_cod_database_code               1551908
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C5(H5), C6(H6), C10(H10), C11(H11), C12(H12)
2.b Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C), C15(H15A,H15B,H15C)
;
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, y+1/2, -z+1/2'
3 '-x, -y, -z'
4 '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
_atom_site_disorder_assembly
_atom_site_disorder_group
F1 F 0.07631(11) -0.0115(2) 0.62382(13) 0.0621(5) Uani 1 1 d . . .
F2 F 0.20563(14) -0.18379(16) 0.70912(12) 0.0619(5) Uani 1 1 d . . .
N1 N 0.32184(14) 0.1635(2) 0.79061(16) 0.0329(5) Uani 1 1 d . . .
N2 N 0.24062(15) 0.0722(2) 0.77496(16) 0.0352(5) Uani 1 1 d . . .
N3 N 0.23212(15) -0.0039(2) 0.58570(15) 0.0336(5) Uani 1 1 d . . .
N4 N 0.5150(2) 0.3544(3) 0.7524(2) 0.0619(7) Uani 1 1 d . . .
C1 C 0.35563(17) 0.1741(2) 0.71018(19) 0.0315(5) Uani 1 1 d . . .
C2 C 0.31394(18) 0.0931(2) 0.60375(19) 0.0312(6) Uani 1 1 d . . .
C3 C 0.3530(2) 0.1107(3) 0.5210(2) 0.0391(6) Uani 1 1 d . . .
H3 H 0.4095 0.1800 0.5328 0.047 Uiso 1 1 calc R . .
C4 C 0.3099(2) 0.0283(3) 0.4232(2) 0.0475(7) Uani 1 1 d . . .
H4 H 0.3372 0.0385 0.3672 0.057 Uiso 1 1 calc R . .
C5 C 0.2258(2) -0.0709(3) 0.4058(2) 0.0498(7) Uani 1 1 d . . .
H5 H 0.1947 -0.1288 0.3379 0.060 Uiso 1 1 calc R . .
C6 C 0.1888(2) -0.0833(3) 0.4877(2) 0.0424(6) Uani 1 1 d . . .
H6 H 0.1307 -0.1498 0.4756 0.051 Uiso 1 1 calc R . .
C7 C 0.4439(2) 0.2752(3) 0.7347(2) 0.0416(6) Uani 1 1 d . . .
C8 C 0.2118(2) 0.0670(3) 0.8707(2) 0.0412(6) Uani 1 1 d . . .
C9 C 0.1226(2) 0.1494(3) 0.8643(2) 0.0526(8) Uani 1 1 d . . .
C10 C 0.0950(3) 0.1376(4) 0.9556(3) 0.0736(11) Uani 1 1 d . . .
H10 H 0.0351 0.1923 0.9544 0.088 Uiso 1 1 calc R . .
C11 C 0.1527(4) 0.0486(5) 1.0469(3) 0.0866(14) Uani 1 1 d . . .
H11 H 0.1309 0.0399 1.1072 0.104 Uiso 1 1 calc R . .
C12 C 0.2419(3) -0.0290(4) 1.0532(3) 0.0698(10) Uani 1 1 d . . .
H12 H 0.2820 -0.0882 1.1185 0.084 Uiso 1 1 calc R . .
C13 C 0.2737(2) -0.0209(3) 0.9642(2) 0.0510(8) Uani 1 1 d . . .
C14 C 0.0602(2) 0.2506(4) 0.7663(3) 0.0680(9) Uani 1 1 d . . .
H14A H 0.0162 0.1890 0.7003 0.102 Uiso 1 1 calc R . .
H14B H 0.1098 0.3126 0.7477 0.102 Uiso 1 1 calc R . .
H14C H 0.0138 0.3166 0.7868 0.102 Uiso 1 1 calc R . .
C15 C 0.3724(2) -0.1019(4) 0.9724(3) 0.0713(10) Uani 1 1 d . . .
H15A H 0.3608 -0.1413 0.8974 0.107 Uiso 1 1 calc R . .
H15B H 0.3880 -0.1860 1.0263 0.107 Uiso 1 1 calc R . .
H15C H 0.4330 -0.0315 0.9988 0.107 Uiso 1 1 calc R . .
B1 B 0.1852(2) -0.0347(3) 0.6756(2) 0.0394(7) 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'
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
C1 N1 N2 118.68(19) . .
N1 N2 C8 113.81(18) . .
N1 N2 B1 126.91(19) . .
C8 N2 B1 118.96(19) . .
C2 N3 B1 123.37(19) . .
C6 N3 C2 119.9(2) . .
C6 N3 B1 116.7(2) . .
N1 C1 C2 126.4(2) . .
N1 C1 C7 114.8(2) . .
C7 C1 C2 118.8(2) . .
N3 C2 C1 116.59(19) . .
N3 C2 C3 119.8(2) . .
C3 C2 C1 123.6(2) . .
C2 C3 H3 120.1 . .
C4 C3 C2 119.9(2) . .
C4 C3 H3 120.1 . .
C3 C4 H4 120.2 . .
C3 C4 C5 119.6(2) . .
C5 C4 H4 120.2 . .
C4 C5 H5 120.6 . .
C6 C5 C4 118.8(2) . .
C6 C5 H5 120.6 . .
N3 C6 C5 122.0(2) . .
N3 C6 H6 119.0 . .
C5 C6 H6 119.0 . .
N4 C7 C1 178.4(3) . .
C9 C8 N2 118.6(2) . .
C13 C8 N2 118.4(2) . .
C13 C8 C9 123.0(2) . .
C8 C9 C14 122.6(2) . .
C10 C9 C8 117.1(3) . .
C10 C9 C14 120.3(3) . .
C9 C10 H10 119.5 . .
C11 C10 C9 121.0(3) . .
C11 C10 H10 119.5 . .
C10 C11 H11 119.4 . .
C10 C11 C12 121.2(3) . .
C12 C11 H11 119.4 . .
C11 C12 H12 119.8 . .
C11 C12 C13 120.3(3) . .
C13 C12 H12 119.8 . .
C8 C13 C12 117.3(3) . .
C8 C13 C15 122.3(2) . .
C12 C13 C15 120.4(3) . .
C9 C14 H14A 109.5 . .
C9 C14 H14B 109.5 . .
C9 C14 H14C 109.5 . .
H14A C14 H14B 109.5 . .
H14A C14 H14C 109.5 . .
H14B C14 H14C 109.5 . .
C13 C15 H15A 109.5 . .
C13 C15 H15B 109.5 . .
C13 C15 H15C 109.5 . .
H15A C15 H15B 109.5 . .
H15A C15 H15C 109.5 . .
H15B C15 H15C 109.5 . .
F1 B1 F2 109.4(2) . .
F1 B1 N2 112.2(2) . .
F1 B1 N3 108.3(2) . .
F2 B1 N2 111.4(2) . .
F2 B1 N3 107.8(2) . .
N2 B1 N3 107.70(19) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
F1 B1 1.375(3) .
F2 B1 1.379(3) .
N1 N2 1.322(2) .
N1 C1 1.310(3) .
N2 C8 1.453(3) .
N2 B1 1.519(3) .
N3 C2 1.354(3) .
N3 C6 1.351(3) .
N3 B1 1.574(3) .
N4 C7 1.144(3) .
C1 C2 1.442(3) .
C1 C7 1.432(3) .
C2 C3 1.394(3) .
C3 H3 0.9500 .
C3 C4 1.363(3) .
C4 H4 0.9500 .
C4 C5 1.393(4) .
C5 H5 0.9500 .
C5 C6 1.360(3) .
C6 H6 0.9500 .
C8 C9 1.398(4) .
C8 C13 1.390(4) .
C9 C10 1.389(4) .
C9 C14 1.494(4) .
C10 H10 0.9500 .
C10 C11 1.364(5) .
C11 H11 0.9500 .
C11 C12 1.377(5) .
C12 H12 0.9500 .
C12 C13 1.396(4) .
C13 C15 1.499(4) .
C14 H14A 0.9800 .
C14 H14B 0.9800 .
C14 H14C 0.9800 .
C15 H15A 0.9800 .
C15 H15B 0.9800 .
C15 H15C 0.9800 .
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
N1 N2 C8 C9 101.5(3) . . . .
N1 N2 C8 C13 -79.0(3) . . . .
N1 N2 B1 F1 -125.9(2) . . . .
N1 N2 B1 F2 111.1(3) . . . .
N1 N2 B1 N3 -6.8(3) . . . .
N1 C1 C2 N3 -0.3(3) . . . .
N1 C1 C2 C3 179.4(2) . . . .
N1 C1 C7 N4 160(11) . . . .
N2 N1 C1 C2 -1.0(3) . . . .
N2 N1 C1 C7 -179.87(19) . . . .
N2 C8 C9 C10 177.8(2) . . . .
N2 C8 C9 C14 -4.1(4) . . . .
N2 C8 C13 C12 -177.5(2) . . . .
N2 C8 C13 C15 3.9(4) . . . .
N3 C2 C3 C4 -1.1(3) . . . .
C1 N1 N2 C8 178.7(2) . . . .
C1 N1 N2 B1 5.2(3) . . . .
C1 C2 C3 C4 179.2(2) . . . .
C2 N3 C6 C5 0.9(4) . . . .
C2 N3 B1 F1 126.6(2) . . . .
C2 N3 B1 F2 -115.1(2) . . . .
C2 N3 B1 N2 5.1(3) . . . .
C2 C1 C7 N4 -19(11) . . . .
C2 C3 C4 C5 1.2(4) . . . .
C3 C4 C5 C6 -0.2(4) . . . .
C4 C5 C6 N3 -0.9(4) . . . .
C6 N3 C2 C1 179.8(2) . . . .
C6 N3 C2 C3 0.1(3) . . . .
C6 N3 B1 F1 -55.3(3) . . . .
C6 N3 B1 F2 63.0(3) . . . .
C6 N3 B1 N2 -176.8(2) . . . .
C7 C1 C2 N3 178.5(2) . . . .
C7 C1 C2 C3 -1.9(3) . . . .
C8 N2 B1 F1 61.0(3) . . . .
C8 N2 B1 F2 -62.0(3) . . . .
C8 N2 B1 N3 -179.9(2) . . . .
C8 C9 C10 C11 -0.3(4) . . . .
C9 C8 C13 C12 1.9(4) . . . .
C9 C8 C13 C15 -176.6(2) . . . .
C9 C10 C11 C12 1.9(5) . . . .
C10 C11 C12 C13 -1.7(5) . . . .
C11 C12 C13 C8 -0.2(4) . . . .
C11 C12 C13 C15 178.4(3) . . . .
C13 C8 C9 C10 -1.7(4) . . . .
C13 C8 C9 C14 176.4(2) . . . .
C14 C9 C10 C11 -178.4(3) . . . .
B1 N2 C8 C9 -84.5(3) . . . .
B1 N2 C8 C13 95.0(3) . . . .
B1 N3 C2 C1 -2.2(3) . . . .
B1 N3 C2 C3 178.1(2) . . . .
B1 N3 C6 C5 -177.2(2) . . . .
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 121514026
