#------------------------------------------------------------------------------
#$Date: 2019-11-11 20:34:14 +0200 (Mon, 11 Nov 2019) $
#$Revision: 227283 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/03/58/4035874.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_4035874
loop_
_publ_author_name
'Lv, Xiaokang'
'Li, Tingting'
'Wu, Qinghua'
'Yu, Changjiang'
'Jiao, Lijuan'
'Hao, Erhong'
_publ_section_title
;
 Polybrominated BOPHY Dyes: Synthesis, Reactivity, and Properties.
;
_journal_issue                   3
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              1134
_journal_page_last               1145
_journal_paper_doi               10.1021/acs.joc.7b02415
_journal_volume                  83
_journal_year                    2018
_chemical_formula_moiety         'C26 H26 B2 F4 N6'
_chemical_formula_sum            'C26 H26 B2 F4 N6'
_chemical_formula_weight         520.15
_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             2016-07-09
_audit_creation_method
;
Olex2 1.2-beta
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_cell_angle_alpha                90
_cell_angle_beta                 94.572(4)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   7.097(2)
_cell_length_b                   8.061(3)
_cell_length_c                   24.763(8)
_cell_measurement_reflns_used    2338
_cell_measurement_temperature    293.15
_cell_measurement_theta_max      23.183
_cell_measurement_theta_min      2.475
_cell_volume                     1412.2(8)
_computing_cell_refinement       'SAINT v7.34A (Bruker, 200?)'
_computing_data_reduction        'SAINT v7.34A (Bruker, 200?)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_diffrn_ambient_temperature      293.15
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0709
_diffrn_reflns_av_unetI/netI     0.0578
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            13764
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.680
_diffrn_reflns_theta_min         1.650
_exptl_absorpt_coefficient_mu    0.092
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.223
_exptl_crystal_description       block
_exptl_crystal_F_000             540
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.242
_refine_diff_density_min         -0.286
_refine_diff_density_rms         0.062
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     174
_refine_ls_number_reflns         2672
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.025
_refine_ls_R_factor_all          0.1228
_refine_ls_R_factor_gt           0.0776
_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)+(0.1118P)²+1.1549P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1993
_refine_ls_wR_factor_ref         0.2277
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1639
_reflns_number_total             2672
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            jo7b02415_si_002.cif
_cod_data_source_block           16
_cod_original_cell_volume        1412.1(8)
_cod_database_code               4035874
_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   0.981
_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:
 C5(H5), C4(H4), C11(H11), C7(H7), C8(H8), C10(H10), C14(H14)
2.b Idealised Me refined as rotating group:
 C2(H2A,H2B,H2C), C1(H1A,H1B,H1C)
;
_shelx_shelxl_version_number     2014/7
_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
N2 N -0.0164(4) 0.1142(4) 0.39963(11) 0.0375(7) Uani 1 1 d .
C6 C 0.0976(5) 0.1784(4) 0.30729(14) 0.0383(9) Uani 1 1 d .
C3 C 0.3340(5) 0.1693(5) 0.21896(14) 0.0417(9) Uani 1 1 d .
C9 C -0.0369(5) 0.1843(4) 0.34883(14) 0.0387(9) Uani 1 1 d .
C5 C 0.2623(5) 0.0829(5) 0.30903(15) 0.0443(9) Uani 1 1 d .
H5 H 0.2957 0.0195 0.3397 0.053 Uiso 1 1 calc R
C4 C 0.3773(5) 0.0800(5) 0.26640(15) 0.0458(10) Uani 1 1 d .
H4 H 0.4870 0.0163 0.2696 0.055 Uiso 1 1 calc R
C11 C -0.3049(5) 0.2344(5) 0.38862(16) 0.0505(10) Uani 1 1 d .
H11 H -0.4258 0.2706 0.3948 0.061 Uiso 1 1 calc R
C12 C -0.1840(5) 0.1440(5) 0.42447(14) 0.0412(9) Uani 1 1 d .
C7 C 0.0566(5) 0.2693(5) 0.26007(16) 0.0482(10) Uani 1 1 d .
H7 H -0.0512 0.3353 0.2573 0.058 Uiso 1 1 calc R
C8 C 0.1688(6) 0.2656(5) 0.21721(16) 0.0518(11) Uani 1 1 d .
H8 H 0.1344 0.3283 0.1865 0.062 Uiso 1 1 calc R
C10 C -0.2147(5) 0.2606(5) 0.34288(16) 0.0501(10) Uani 1 1 d .
H10 H -0.2632 0.3195 0.3126 0.060 Uiso 1 1 calc R
C2 C 0.6209(6) 0.0782(6) 0.17996(18) 0.0628(12) Uani 1 1 d .
H2A H 0.6992 0.1157 0.2110 0.094 Uiso 1 1 calc GR
H2B H 0.6843 0.0976 0.1477 0.094 Uiso 1 1 calc GR
H2C H 0.5965 -0.0383 0.1834 0.094 Uiso 1 1 calc GR
C1 C 0.3845(7) 0.2447(7) 0.12584(18) 0.0739(15) Uani 1 1 d .
H1A H 0.2729 0.1899 0.1103 0.111 Uiso 1 1 calc GR
H1B H 0.4825 0.2369 0.1014 0.111 Uiso 1 1 calc GR
H1C H 0.3566 0.3593 0.1321 0.111 Uiso 1 1 calc GR
C14 C 0.2116(5) -0.0930(5) 0.52436(15) 0.0422(9) Uani 1 1 d .
H14 H 0.3297 -0.1144 0.5121 0.051 Uiso 1 1 calc R
N4 N 0.0875(4) -0.0161(4) 0.49026(11) 0.0396(8) Uani 1 1 d .
N1 N 0.4470(5) 0.1665(4) 0.17665(13) 0.0520(9) Uani 1 1 d .
B1 B 0.1410(6) 0.0124(6) 0.43033(17) 0.0436(11) Uani 1 1 d .
F1 F 0.3115(3) 0.0926(4) 0.43394(9) 0.0678(8) Uani 1 1 d .
F2 F 0.1580(4) -0.1405(3) 0.40663(10) 0.0695(8) 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
C9 N2 C12 107.4(3) . .
C9 N2 B1 133.7(3) . .
C12 N2 B1 118.9(3) . .
C5 C6 C9 126.1(3) . .
C7 C6 C9 118.1(3) . .
C7 C6 C5 115.8(3) . .
C4 C3 C8 116.1(3) . .
N1 C3 C4 122.2(4) . .
N1 C3 C8 121.6(3) . .
N2 C9 C6 127.1(3) . .
N2 C9 C10 107.8(3) . .
C10 C9 C6 125.1(3) . .
C4 C5 C6 121.9(4) . .
C5 C4 C3 122.0(4) . .
C10 C11 C12 107.8(3) . .
C11 C12 N2 108.2(3) . .
C14 C12 N2 123.1(3) 3_556 .
C14 C12 C11 128.7(3) 3_556 .
C8 C7 C6 122.8(4) . .
C7 C8 C3 121.4(4) . .
C11 C10 C9 108.9(3) . .
N4 C14 C12 126.7(3) . 3_556
C14 N4 N4 115.7(3) . 3_556
C14 N4 B1 118.1(3) . .
N4 N4 B1 125.9(3) 3_556 .
C3 N1 C2 121.5(3) . .
C3 N1 C1 120.1(3) . .
C2 N1 C1 118.3(3) . .
N2 B1 N4 108.9(3) . .
F1 B1 N2 112.5(3) . .
F1 B1 N4 106.6(3) . .
F1 B1 F2 110.1(3) . .
F2 B1 N2 110.6(3) . .
F2 B1 N4 107.9(3) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
N2 C9 1.376(4) .
N2 C12 1.403(4) .
N2 B1 1.537(5) .
C6 C9 1.459(5) .
C6 C5 1.398(5) .
C6 C7 1.391(5) .
C3 C4 1.391(5) .
C3 C8 1.404(5) .
C3 N1 1.370(4) .
C9 C10 1.401(5) .
C5 C4 1.385(5) .
C11 C12 1.391(5) .
C11 C10 1.361(5) .
C12 C14 1.361(5) 3_556
C7 C8 1.377(5) .
C2 N1 1.421(5) .
C1 N1 1.445(5) .
C14 C12 1.361(5) 3_556
C14 N4 1.324(4) .
N4 N4 1.393(5) 3_556
N4 B1 1.578(5) .
B1 F1 1.369(5) .
B1 F2 1.375(5) .
