Further investigation on the nitration of BODIPY with cupric nitrate: crystal structures of 4,4-difluoro-1,3,5,7,8-pentamethyl-2-nitro-4-bora-3a,4a-diaza-<i>s</i>-indacene, 4,4-difluoro-3-nitro-8-phenyl-4-bora-3a,4a-diaza-<i>s</i>-indacene, and 3-chloro-6-ethyl-5,7,8-trimethyl-2-nitro-4,4-diphenyl-4-bora-3a,4a-diaza-<i>s</i>-indacene
Joshi, Dhruval J.; Jun, Meesook; Yang, Lijing; Lough, Alan J.; Yan, Hongbin; Acta Crystallographica Section E 74 (2018) 103–108; doi:10.1107/S2056989017018564

data_2242320
_publ_section_title
;
 Further investigation on the nitration of BODIPY with cupric nitrate:
 crystal structures of
 4,4-difluoro-1,3,5,7,8-pentamethyl-2-nitro-4-bora-3a,4a-diaza-<i>s</i>-indacene,
 4,4-difluoro-3-nitro-8-phenyl-4-bora-3a,4a-diaza-<i>s</i>-indacene, and
 3-chloro-6-ethyl-5,7,8-trimethyl-2-nitro-4,4-diphenyl-4-bora-3a,4a-diaza-<i>s</i>-indacene
;
_journal_issue                   2
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              103
_journal_page_last               108
_journal_paper_doi               10.1107/S2056989017018564
_journal_volume                  74
_journal_year                    2018
_chemical_formula_iupac          'C26 H25 B Cl N3 O2'
_chemical_formula_moiety         'C26 H25 B Cl N3 O2'
_chemical_formula_sum            'C26 H25 B Cl N3 O2'
_chemical_formula_weight         457.75
_chemical_name_systematic
3-Chloro-6-ethyl-5,7,8-trimethyl-2-nitro-4,4-diphenyl-4-bora-3a,4a-diaza-<i>s</i>-indacene
_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_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2016/6
_cell_angle_alpha                90
_cell_angle_beta                 104.1160(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.8359(4)
_cell_length_b                   12.0825(4)
_cell_length_c                   16.5811(5)
_cell_measurement_reflns_used    9143
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      66.90
_cell_measurement_theta_min      4.15
_cell_volume                     2299.62(13)
_computing_cell_refinement
;
APEX2 (Bruker, 2014)
;
_computing_data_collection
;
APEX2 (Bruker, 2014)
;
_computing_data_reduction
;
SAINT (Bruker, 2014)
;
_computing_molecular_graphics
;
PLATON (Spek, 2009)
;
_computing_publication_material
;
SHELXTL (Sheldrick, 2008)
;
_computing_structure_refinement
;
<i>SHELXL2016/6</i> (Sheldrick, 2015b)
;
_computing_structure_solution
;
SHELXT (Sheldrick, 2015a)
;
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Bruker Kappa APEX-DUO CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0473
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            43708
_diffrn_reflns_theta_full        67.022
_diffrn_reflns_theta_max         67.022
_diffrn_reflns_theta_min         4.150
_exptl_absorpt_coefficient_mu    1.698
_exptl_absorpt_correction_T_max  0.7529
_exptl_absorpt_correction_T_min  0.5856
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(SADABS, Bruker, 2014)
;
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.322
_exptl_crystal_description       Block
_exptl_crystal_F_000             960
_exptl_crystal_size_max          0.190
_exptl_crystal_size_mid          0.180
_exptl_crystal_size_min          0.100
_refine_diff_density_max         0.267
_refine_diff_density_min         -0.290
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     330
_refine_ls_number_reflns         4080
_refine_ls_number_restraints     8
_refine_ls_restrained_S_all      1.046
_refine_ls_R_factor_all          0.0344
_refine_ls_R_factor_gt           0.0328
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0370P)^2^+1.0066P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0834
_refine_ls_wR_factor_ref         0.0849
_reflns_number_gt                3864
_reflns_number_total             4080
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            hb7723sup1.cif
_cod_data_source_block           5d
_cod_database_code               2242320
_shelx_estimated_absorpt_t_min   0.739
_shelx_estimated_absorpt_t_max   0.849
_shelx_hkl_checksum              73306
_shelx_res_checksum              31396
_cod_database_fobs_code 2242320