Near-Infrared Absorbing Azo Dyes: Synthesis and X-ray Crystallographic and Spectral Characterization of Monoazopyrroles, Bisazopyrroles, and a Boron-Azopyrrole Complex
Yan Li; Brian O. Patrick; David Dolphin; Journal of Organic Chemistry 74 (2009) 5237–5243; doi:10.1021/jo9003019

data_4024654
_publ_section_title
;
Near-Infrared Absorbing Azo Dyes: Synthesis and X-ray Crystallographic and
Spectral Characterization of Monoazopyrroles, Bisazopyrroles, and a
Boron-Azopyrrole Complex
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              5237
_journal_page_last               5243
_journal_paper_doi               10.1021/jo9003019
_journal_volume                  74
_journal_year                    2009
_chemical_formula_sum            'C21 H25 Cl2 N7'
_chemical_formula_weight         446.38
_space_group_IT_number           31
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac -2'
_symmetry_space_group_name_H-M   'P m n 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   24.358(2)
_cell_length_b                   6.0556(4)
_cell_length_c                   7.4113(4)
_cell_measurement_reflns_used    6101
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      26.94
_cell_measurement_theta_min      2.87
_cell_volume                     1093.18(13)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker X8 APEX'
_diffrn_measurement_method       'area detector'
_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  0.0289
_diffrn_reflns_av_sigmaI/netI    0.0234
_diffrn_reflns_limit_h_max       32
_diffrn_reflns_limit_h_min       -32
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            17280
_diffrn_reflns_theta_full        28.00
_diffrn_reflns_theta_max         28.00
_diffrn_reflns_theta_min         1.67
_exptl_absorpt_coefficient_mu    0.320
_exptl_absorpt_correction_T_max  0.908
_exptl_absorpt_correction_T_min  0.841
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            black
_exptl_crystal_density_diffrn    1.356
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             468
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.50
_exptl_crystal_size_min          0.30
_refine_diff_density_max         0.321
_refine_diff_density_min         -0.424
_refine_diff_density_rms         0.048
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.02(9)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     151
_refine_ls_number_reflns         2645
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.041
_refine_ls_R_factor_all          0.0454
_refine_ls_R_factor_gt           0.0391
_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/[\s^2^(Fo^2^)+(0.0588P)^2^+0.3213P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1011
_refine_ls_wR_factor_ref         0.1048
_reflns_number_gt                2343
_reflns_number_total             2645
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo9003019_si_003.cif
_cod_data_source_block           2a
_cod_original_sg_symbol_H-M      Pmn21
_cod_database_code               4024654