Polybrominated BOPHY Dyes: Synthesis, Reactivity, and Properties.
Lv, Xiaokang; Li, Tingting; Wu, Qinghua; Yu, Changjiang; Jiao, Lijuan; Hao, Erhong; The Journal of organic chemistry 83 (2018) 1134–1145; doi:10.1021/acs.joc.7b02415

data_4035873
_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         'C24 H27 B2 Br2 F4 N6'
_chemical_formula_sum            'C24 H27 B2 Br2 F4 N6'
_chemical_formula_weight         656.97
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_Int_Tables_number      14
_audit_creation_date             2017-07-18
_audit_creation_method
;
Olex2 1.2-beta
(compiled 2016.11.30 svn.r3356 for OlexSys, GUI svn.r5269)
;
_cell_angle_alpha                90
_cell_angle_beta                 110.002(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   17.745(3)
_cell_length_b                   8.6108(16)
_cell_length_c                   19.469(4)
_cell_measurement_reflns_used    5765
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      24.82
_cell_measurement_theta_min      2.44
_cell_volume                     2795.4(9)
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine (Bourhis et al., 2015)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD area detector'
_diffrn_detector_area_resol_mean 5.6
_diffrn_detector_type            'Bruker SMART CCD 6000 area detector'
_diffrn_measured_fraction_theta_full 0.9963
_diffrn_measured_fraction_theta_max 0.9963
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0711
_diffrn_reflns_av_unetI/netI     0.0563
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            20453
_diffrn_reflns_theta_full        25.3647
_diffrn_reflns_theta_max         25.36
_diffrn_reflns_theta_min         1.34
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_target            Mo
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.952
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_correction_T_min  0.4854
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.1071 before and 0.0554 after correction.
The Ratio of minimum to maximum transmission is 0.6514.
The \l/2 correction factor is 0.00150.
;
_exptl_crystal_colour            'metallic yellowish yellow'
_exptl_crystal_colour_lustre     metallic
_exptl_crystal_colour_modifier   yellowish
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.5609
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       cube
_exptl_crystal_F_000             1314.3979
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.2
_refine_diff_density_max         1.1737
_refine_diff_density_min         -0.8651
_refine_diff_density_rms         0.1300
_refine_ls_d_res_high            0.8296
_refine_ls_d_res_low             15.1762
_refine_ls_goodness_of_fit_ref   1.0419
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    42
_refine_ls_number_parameters     347
_refine_ls_number_reflns         5119
_refine_ls_number_restraints     32
_refine_ls_restrained_S_all      1.0384
_refine_ls_R_factor_all          0.0835
_refine_ls_R_factor_gt           0.0541
_refine_ls_shift/su_max          0.0000
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0840P)^2^+2.7000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1417
_refine_ls_wR_factor_ref         0.1608
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              12
_reflns_limit_h_min              -21
_reflns_limit_k_max              10
_reflns_limit_k_min              0
_reflns_limit_l_max              23
_reflns_limit_l_min              -12
_reflns_number_gt                3597
_reflns_number_total             5119
_reflns_threshold_expression     I>=2u(I)
_cod_data_source_file            jo7b02415_si_002.cif
_cod_data_source_block           14
_cod_original_sg_symbol_Hall     '-P 2ybc (x-z,y,z)'
_cod_database_code               4035873
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Rigid bond restraints
 N6, C13
 with sigma for 1-2 distances of 0.02 and sigma for 1-3 distances of 0.01
 C13, C14
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.02
 C21, C22, C23, C24
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.02
3. Uiso/Uaniso restraints and constraints
C13 \\sim C14: within 2A with sigma of 0.01 and sigma for terminal atoms of 0.02
C21 \\sim C22 \\sim C23 \\sim C24: within 2A with sigma of 0.01 and sigma for
terminal atoms of 0.02
4.a Secondary CH2 refined with riding coordinates:
 C11(H11a,H11b), C13(H13a,H13b)
4.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C5(H5), C6(H6), C8(H8), C16(H16), C17(H17), C19(H19), C20(H20)
4.c Idealised Me refined as rotating group:
 C12(H12a,H12b,H12c), C14(H14a,H14b,H14c), C22(H22a,H22b,H22c), C23(H23a,H23b,
 H23c), C24(H24a,H24b,H24c)
;
_olex2_submission_special_instructions 'No special instructions were received'