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_4024061
_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 H17 B N4'
_chemical_formula_weight         348.21
_space_group_IT_number           33
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2c -2n'
_symmetry_space_group_name_H-M   'P n a 21'
_atom_sites_solution_hydrogens   difmap
_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            4
_cell_length_a                   13.5897(2)
_cell_length_b                   14.3599(2)
_cell_length_c                   9.2557(2)
_cell_measurement_reflns_used    6735
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      61
_cell_measurement_theta_min      3
_cell_volume                     1806.22(5)
_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  'SHELXL-97 v.97-2 (Sheldrick, 1993-1997)'
_computing_structure_solution    'XS/SHELXTL v6.12 (Bruker, 2001)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.983
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measurement_device_type  'Bruker APEX2 CCD detector'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0260
_diffrn_reflns_av_sigmaI/netI    0.0124
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            14900
_diffrn_reflns_theta_full        61.28
_diffrn_reflns_theta_max         61.28
_diffrn_reflns_theta_min         4.48
_exptl_absorpt_coefficient_mu    0.603
_exptl_absorpt_correction_T_max  0.9203
_exptl_absorpt_correction_T_min  0.9097
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            'pale yellow'
_exptl_crystal_density_diffrn    1.280
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             728
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.14
_refine_diff_density_max         0.137
_refine_diff_density_min         -0.121
_refine_diff_density_rms         0.026
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.2(4)
_refine_ls_extinction_coef       0.0002(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   0.988
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     313
_refine_ls_number_reflns         1472
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      0.987
_refine_ls_R_factor_all          0.0267
_refine_ls_R_factor_gt           0.0251
_refine_ls_shift/su_max          0.024
_refine_ls_shift/su_mean         0.002
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0529P)^2^+0.1970P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0652
_refine_ls_wR_factor_ref         0.0662
_reflns_number_gt                1415
_reflns_number_total             1472
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo0705420si20070315_044550_5.cif
_cod_data_source_block           BORAZAN7
_cod_database_code               4024061