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_4035872
_publ_section_title
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 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         '2(C10 H12 B Br2.5 F2 N4)'
_chemical_formula_sum            'C20 H24 B2 Br5 F4 N8'
_chemical_formula_weight         873.63
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_Int_Tables_number      2
_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                79.967(9)
_cell_angle_beta                 85.892(9)
_cell_angle_gamma                85.819(10)
_cell_formula_units_Z            1
_cell_length_a                   6.275(5)
_cell_length_b                   10.748(8)
_cell_length_c                   11.424(9)
_cell_measurement_reflns_used    3113
_cell_measurement_temperature    293.15
_cell_measurement_theta_max      26.874
_cell_measurement_theta_min      2.413
_cell_volume                     755.3(10)
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_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)'
_diffrn_ambient_temperature      293.15
_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 0.9843
_diffrn_measured_fraction_theta_max 0.9843
_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  0.0311
_diffrn_reflns_av_unetI/netI     0.0398
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            8912
_diffrn_reflns_theta_full        27.4047
_diffrn_reflns_theta_max         27.40
_diffrn_reflns_theta_min         1.81
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_target            Mo
_exptl_absorpt_coefficient_mu    6.701
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.5484
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.1066 before and 0.0398 after correction.
The Ratio of minimum to maximum transmission is 0.7355.
The \l/2 correction factor is 0.00150.
;
_exptl_crystal_colour            'metallic light colourless'
_exptl_crystal_colour_lustre     metallic
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.9205
_exptl_crystal_description       cube
_exptl_crystal_F_000             419.8772
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.21
_refine_diff_density_max         1.3456
_refine_diff_density_min         -1.1694
_refine_diff_density_rms         0.1480
_refine_ls_d_res_high            0.7721
_refine_ls_d_res_low             11.2290
_refine_ls_goodness_of_fit_ref   1.0194
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    19
_refine_ls_number_parameters     181
_refine_ls_number_reflns         3387
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.0194
_refine_ls_R_factor_all          0.0757
_refine_ls_R_factor_gt           0.0454
_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^)+(0.0434P)^2^+1.4390P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1001
_refine_ls_wR_factor_ref         0.1138
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              8
_reflns_limit_h_min              -8
_reflns_limit_k_max              13
_reflns_limit_k_min              -13
_reflns_limit_l_max              14
_reflns_limit_l_min              0
_reflns_number_gt                2306
_reflns_number_total             3387
_reflns_threshold_expression     I>=2u(I)
_cod_data_source_file            jo7b02415_si_002.cif
_cod_data_source_block           11
_cod_database_code               4035872
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Others
 Fixed Sof: Br1(0.5)
3.a Secondary CH2 refined with riding coordinates:
 C7(H7a,H7b), C8(H8a,H8b), C9(H9a,H9b)
3.b Aromatic/amide H refined with riding coordinates:
 N1(H1), C5(H5), C11(H11)
3.c Idealised Me refined as rotating group:
 C10(H10a,H10b,H10c)
;
_olex2_submission_special_instructions 'No special instructions were received'