BORAZANs: Tunable Fluorophores Based on 2-(Pyrazolyl)aniline Chelates of Diphenylboron
Brendan J. Liddle; Rosalice M. Silva; Tyler J. Morin; Felipe P. Macedo; Ruchi Shukla; Sergey V. Lindeman; James R. Gardinier; Journal of Organic Chemistry 72 (2007) 5637–5646; doi:10.1021/jo0705420

data_4024058
_publ_section_title
;
 BORAZANs: Tunable Fluorophores Based on 2-(Pyrazolyl)aniline
 Chelates of Diphenylboron
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              5637
_journal_page_last               5646
_journal_paper_doi               10.1021/jo0705420
_journal_volume                  72
_journal_year                    2007
_chemical_formula_sum            'C22 H20 B N3 O'
_chemical_formula_weight         353.22
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/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                 98.9610(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   12.5847(9)
_cell_length_b                   15.0987(11)
_cell_length_c                   9.6289(7)
_cell_measurement_reflns_used    4568
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      31
_cell_measurement_theta_min      2.5
_cell_volume                     1807.3(2)
_computing_cell_refinement       'SAINT v7.23A (Bruker, 2005)'
_computing_data_collection       'APEX2 v2.0-2 (Bruker, 2005)'
_computing_data_reduction        'SADABS-2004/1 (Bruker, 2005)'
_computing_molecular_graphics    'XP v5.1 (Bruker, 1998)'
_computing_publication_material  'XCIF v6.12 (Bruker, 2001)'
_computing_structure_refinement  'XL/SHELXTL v6.10 (Bruker, 2001)'
_computing_structure_solution    'XS/SHELXTL v6.12 (Bruker, 2001)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.880
_diffrn_measured_fraction_theta_max 0.880
_diffrn_measurement_device_type  'Bruker APEX2 CCD detector'
_diffrn_measurement_method       'omega scan'
_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  0.0213
_diffrn_reflns_av_sigmaI/netI    0.0250
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            14730
_diffrn_reflns_theta_full        31.94
_diffrn_reflns_theta_max         31.94
_diffrn_reflns_theta_min         1.64
_exptl_absorpt_coefficient_mu    0.080
_exptl_absorpt_correction_T_max  0.9865
_exptl_absorpt_correction_T_min  0.9763
_exptl_absorpt_correction_type   'semi-empirical (SADABS procedure)'
_exptl_crystal_colour            'pale yellow'
_exptl_crystal_density_diffrn    1.298
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             744
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.17
_refine_diff_density_max         0.449
_refine_diff_density_min         -0.237
_refine_diff_density_rms         0.049
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.075
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     324
_refine_ls_number_reflns         5493
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.075
_refine_ls_R_factor_all          0.0595
_refine_ls_R_factor_gt           0.0465
_refine_ls_shift/su_max          0.018
_refine_ls_shift/su_mean         0.002
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0815P)^2^+0.0812P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1240
_refine_ls_wR_factor_ref         0.1316
_reflns_number_gt                4389
_reflns_number_total             5493
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo0705420si20070315_044550_2.cif
_cod_data_source_block           BORAZAN1
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               4024058