#------------------------------------------------------------------------------
#$Date: 2019-09-18 10:11:10 +0300 (Wed, 18 Sep 2019) $
#$Revision: 218415 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/23/39/7233925.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_7233925
loop_
_publ_author_name
'Zhenqi Zhang'
'Pengchong Xue'
'Peng Gong'
'Gonghe Zhang'
'Jiang Peng'
'Ran Lu'
_publ_section_title
;
 Mechanofluorochromic behaviors of beta-iminoenolate boron complexes
 functionalized with carbazole
;
_journal_name_full               'Journal of Materials Chemistry C'
_journal_page_first              9543
_journal_page_last               9551
_journal_paper_doi               10.1039/C4TC01639D
_journal_volume                  2
_journal_year                    2014
_chemical_formula_sum            'C25 H17 B F2 N2 O'
_chemical_formula_weight         410.22
_space_group_IT_number           33
_space_group_name_Hall           'P 2c -2n'
_space_group_name_H-M_alt        'P n a 21'
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'P n a 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   14.306(3)
_cell_length_b                   10.163(2)
_cell_length_c                   13.511(3)
_cell_measurement_reflns_used    16381
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      54.94
_cell_measurement_theta_min      6.03
_cell_volume                     1964.4(7)
_computing_cell_refinement       RAPID-AUTO
_computing_data_collection       'RAPID-AUTO (Rigaku Corporation, 1998)'
_computing_data_reduction
'CrystalStructure (Rigaku/MSC and Rigaku Corporation, 2002)'
_computing_molecular_graphics    'ORTEP-II (Johnson, 1976)'
_computing_publication_material  SHELXL-97
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      295(2)
_diffrn_detector_area_resol_mean 10.000
_diffrn_measured_fraction_theta_full 0.981
_diffrn_measured_fraction_theta_max 0.981
_diffrn_measurement_device_type  'Rigaku RAXIS-RAPID'
_diffrn_measurement_method       'ω scan'
_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  0.0352
_diffrn_reflns_av_sigmaI/netI    0.0304
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            17919
_diffrn_reflns_theta_full        27.45
_diffrn_reflns_theta_max         27.45
_diffrn_reflns_theta_min         3.02
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.098
_exptl_absorpt_correction_T_max  0.9874
_exptl_absorpt_correction_T_min  0.9855
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'ABSCOR (Higashi, 1995)'
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.387
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             848
_exptl_crystal_recrystallization_method 'Vapour Deposition'
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.13
_refine_diff_density_max         0.336
_refine_diff_density_min         -0.142
_refine_diff_density_rms         0.050
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     280
_refine_ls_number_reflns         4403
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.044
_refine_ls_R_factor_all          0.0446
_refine_ls_R_factor_gt           0.0382
_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)+(0.0610P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0919
_refine_ls_wR_factor_ref         0.0948
_reflns_number_gt                3850
_reflns_number_total             4403
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            J-Mater-Chem-C-2014-2-9543.cif
_cod_data_source_block           cc
_cod_original_cell_volume        1964.3(7)
_cod_original_sg_symbol_H-M      Pna2(1)
_cod_database_code               7233925
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, z+1/2'
'x+1/2, -y+1/2, z'
'-x+1/2, 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
B1 B 0.05071(12) 0.1795(2) 0.37649(15) 0.0337(5) Uani 1 1 d . . .
C1 C 0.53049(12) 0.13092(15) -0.02260(11) 0.0282(4) Uani 1 1 d . . .
C2 C 0.48862(14) 0.23860(17) -0.06910(14) 0.0380(4) Uani 1 1 d . . .
H2A H 0.4275 0.2635 -0.0551 0.046 Uiso 1 1 calc R . .
C3 C 0.54322(17) 0.3068(2) -0.13755(14) 0.0485(6) Uani 1 1 d . . .
H3A H 0.5169 0.3776 -0.1711 0.058 Uiso 1 1 calc R . .
C4 C 0.63655(18) 0.2725(2) -0.15777(14) 0.0530(6) Uani 1 1 d . . .
H4A H 0.6704 0.3210 -0.2039 0.064 Uiso 1 1 calc R . .
C5 C 0.67888(15) 0.16721(19) -0.10988(14) 0.0439(5) Uani 1 1 d . . .
H5A H 0.7409 0.1456 -0.1226 0.053 Uiso 1 1 calc R . .
C6 C 0.62559(12) 0.09379(17) -0.04144(12) 0.0324(4) Uani 1 1 d . . .
C7 C 0.64577(10) -0.01900(17) 0.01952(12) 0.0297(4) Uani 1 1 d . . .
C8 C 0.72501(11) -0.10105(19) 0.03001(14) 0.0368(4) Uani 1 1 d . . .
H8A H 0.7787 -0.0861 -0.0072 0.044 Uiso 1 1 calc R . .
C9 C 0.72096(13) -0.2038(2) 0.09668(14) 0.0407(5) Uani 1 1 d . . .
H9A H 0.7728 -0.2578 0.1055 0.049 Uiso 1 1 calc R . .
C10 C 0.63876(13) -0.22766(19) 0.15156(14) 0.0386(4) Uani 1 1 d . . .
H10A H 0.6379 -0.2977 0.1959 0.046 Uiso 1 1 calc R . .
C11 C 0.55789(11) -0.14930(17) 0.14178(13) 0.0307(4) Uani 1 1 d . . .
H11A H 0.5040 -0.1667 0.1779 0.037 Uiso 1 1 calc R . .
C12 C 0.56268(11) -0.04487(15) 0.07552(12) 0.0253(3) Uani 1 1 d . . .
C13 C 0.40083(11) 0.05754(15) 0.09190(11) 0.0239(3) Uani 1 1 d . . .
C14 C 0.32101(11) 0.06913(15) 0.03115(12) 0.0279(3) Uani 1 1 d . . .
H14A H 0.3278 0.0668 -0.0373 0.033 Uiso 1 1 calc R . .
C15 C 0.23126(11) 0.08418(16) 0.07233(12) 0.0270(3) Uani 1 1 d . . .
H15A H 0.1795 0.0920 0.0311 0.032 Uiso 1 1 calc R . .
C16 C 0.21959(11) 0.08743(14) 0.17553(12) 0.0231(3) Uani 1 1 d . . .
C17 C 0.30030(10) 0.07425(14) 0.23524(11) 0.0227(3) Uani 1 1 d . . .
H17A H 0.2937 0.0756 0.3037 0.027 Uiso 1 1 calc R . .
C18 C 0.39020(11) 0.05923(15) 0.19447(11) 0.0238(3) Uani 1 1 d . . .
H18A H 0.4420 0.0505 0.2355 0.029 Uiso 1 1 calc R . .
C19 C 0.12500(10) 0.10647(15) 0.22200(11) 0.0228(3) Uani 1 1 d . . .
C20 C 0.04067(11) 0.10703(16) 0.17350(12) 0.0269(3) Uani 1 1 d . . .
H20A H 0.0405 0.1011 0.1048 0.032 Uiso 1 1 calc R . .
C21 C -0.04845(10) 0.11652(15) 0.22490(12) 0.0239(3) Uani 1 1 d . . .
C22 C -0.13660(11) 0.09181(16) 0.17914(13) 0.0292(4) Uani 1 1 d . . .
H22A H -0.1389 0.0717 0.1120 0.035 Uiso 1 1 calc R . .
C23 C -0.21930(11) 0.09733(16) 0.23351(14) 0.0314(4) Uani 1 1 d . . .
H23A H -0.2765 0.0810 0.2031 0.038 Uiso 1 1 calc R . .
C24 C -0.21524(11) 0.12754(16) 0.33384(14) 0.0301(4) Uani 1 1 d . . .
H24A H -0.2695 0.1319 0.3716 0.036 Uiso 1 1 calc R . .
C25 C -0.12849(11) 0.15101(16) 0.37629(13) 0.0287(3) Uani 1 1 d . . .
H25A H -0.1255 0.1711 0.4434 0.034 Uiso 1 1 calc R . .
N1 N 0.49306(9) 0.04664(13) 0.04936(9) 0.0263(3) Uani 1 1 d . . .
N2 N -0.04688(9) 0.14573(13) 0.32304(11) 0.0243(3) Uani 1 1 d . . .
O1 O 0.12840(7) 0.11951(13) 0.32097(8) 0.0307(3) Uani 1 1 d . . .
F1 F 0.04887(7) 0.12875(17) 0.46993(8) 0.0623(4) Uani 1 1 d . . .
F2 F 0.05923(7) 0.31478(13) 0.37685(11) 0.0592(4) 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'
N N 0.0061 0.0033 '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'
F F 0.0171 0.0103 '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
F1 B1 F2 112.01(18) . .
F1 B1 O1 109.25(16) . .
F2 B1 O1 110.32(16) . .
F1 B1 N2 108.56(15) . .
F2 B1 N2 106.88(15) . .
O1 B1 N2 109.77(14) . .
C2 C1 N1 128.81(16) . .
C2 C1 C6 122.20(15) . .
N1 C1 C6 108.94(15) . .
C3 C2 C1 116.58(19) . .
C2 C3 C4 122.5(2) . .
C5 C4 C3 120.94(18) . .
C4 C5 C6 118.5(2) . .
C5 C6 C1 119.30(18) . .
C5 C6 C7 133.38(18) . .
C1 C6 C7 107.32(13) . .
C8 C7 C12 120.25(16) . .
C8 C7 C6 133.38(15) . .
C12 C7 C6 106.35(14) . .
C9 C8 C7 118.53(16) . .
C8 C9 C10 120.52(16) . .
C11 C10 C9 122.50(19) . .
C12 C11 C10 116.79(16) . .
C11 C12 N1 129.14(14) . .
C11 C12 C7 121.39(15) . .
N1 C12 C7 109.45(14) . .
C18 C13 C14 119.26(14) . .
C18 C13 N1 119.77(14) . .
C14 C13 N1 120.97(13) . .
C15 C14 C13 121.15(14) . .
C16 C15 C14 120.23(15) . .
C15 C16 C17 117.82(15) . .
C15 C16 C19 121.62(14) . .
C17 C16 C19 120.55(13) . .
C18 C17 C16 122.20(14) . .
C13 C18 C17 119.35(15) . .
O1 C19 C20 120.39(14) . .
O1 C19 C16 113.28(13) . .
C20 C19 C16 126.29(14) . .
C19 C20 C21 122.85(15) . .
N2 C21 C22 118.42(14) . .
N2 C21 C20 117.76(14) . .
C22 C21 C20 123.78(15) . .
C23 C22 C21 120.98(15) . .
C24 C23 C22 119.15(15) . .
C25 C24 C23 118.55(15) . .
N2 C25 C24 122.51(15) . .
C1 N1 C12 107.91(13) . .
C1 N1 C13 125.34(13) . .
C12 N1 C13 126.68(13) . .
C21 N2 C25 120.39(14) . .
C21 N2 B1 119.92(13) . .
C25 N2 B1 119.65(13) . .
C19 O1 B1 121.33(13) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
B1 F1 1.364(3) .
B1 F2 1.381(3) .
B1 O1 1.473(2) .
B1 N2 1.609(2) .
C1 C2 1.397(3) .
C1 N1 1.402(2) .
C1 C6 1.435(2) .
C2 C3 1.395(3) .
C3 C4 1.407(3) .
C4 C5 1.389(3) .
C5 C6 1.412(2) .
C6 C7 1.441(3) .
C7 C8 1.414(2) .
C7 C12 1.433(2) .
C8 C9 1.380(3) .
C9 C10 1.411(3) .
C10 C11 1.411(2) .
C11 C12 1.390(2) .
C12 N1 1.408(2) .
C13 C18 1.394(2) .
C13 C14 1.411(2) .
C13 N1 1.443(2) .
C14 C15 1.408(2) .
C15 C16 1.405(2) .
C16 C17 1.415(2) .
C16 C19 1.504(2) .
C17 C18 1.407(2) .
C19 O1 1.3447(19) .
C19 C20 1.373(2) .
C20 C21 1.455(2) .
C21 N2 1.359(2) .
C21 C22 1.427(2) .
C22 C23 1.394(2) .
C23 C24 1.391(3) .
C24 C25 1.388(2) .
C25 N2 1.372(2) .
