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_4024655
_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            'C16 H13 N5 O2'
_chemical_formula_weight         307.31
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_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                 98.849(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   33.590(3)
_cell_length_b                   5.3632(5)
_cell_length_c                   16.252(2)
_cell_measurement_reflns_used    9562
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      27.61
_cell_measurement_theta_min      2.53
_cell_volume                     2892.9(5)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.991
_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     0.71069
_diffrn_reflns_av_R_equivalents  0.0303
_diffrn_reflns_av_sigmaI/netI    0.0213
_diffrn_reflns_limit_h_max       44
_diffrn_reflns_limit_h_min       -44
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            35349
_diffrn_reflns_theta_full        27.86
_diffrn_reflns_theta_max         27.86
_diffrn_reflns_theta_min         1.23
_exptl_absorpt_coefficient_mu    0.098
_exptl_absorpt_correction_T_max  0.990
_exptl_absorpt_correction_T_min  0.875
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            'dark red'
_exptl_crystal_density_diffrn    1.411
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       rod
_exptl_crystal_F_000             1280
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.263
_refine_diff_density_min         -0.190
_refine_diff_density_rms         0.037
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.069
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     220
_refine_ls_number_reflns         3411
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.069
_refine_ls_R_factor_all          0.0504
_refine_ls_R_factor_gt           0.0356
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0441P)^2^+1.4753P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0905
_refine_ls_wR_factor_ref         0.0972
_reflns_number_gt                2631
_reflns_number_total             3411
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo9003019_si_004.cif
_cod_data_source_block           2b
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               4024655