#------------------------------------------------------------------------------
#$Date: 2016-03-21 03:04:54 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178419 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/40/4024060.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_4024060
loop_
_publ_author_name
'Brendan J. Liddle'
'Rosalice M. Silva'
'Tyler J. Morin'
'Felipe P. Macedo'
'Ruchi Shukla'
'Sergey V. Lindeman'
'James R. Gardinier'
_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 F3 N3'
_chemical_formula_weight         391.20
_chemical_name_systematic
; 
 ? 
;
_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   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 92.567(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   13.315(4)
_cell_length_b                   15.279(4)
_cell_length_c                   9.319(2)
_cell_measurement_reflns_used    3545
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      22.5
_cell_measurement_theta_min      2.5
_cell_volume                     1894.0(9)
_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 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker APEX2 CCD detector'
_diffrn_measurement_method       'ω scans'
_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  0.0575
_diffrn_reflns_av_sigmaI/netI    0.0479
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            30441
_diffrn_reflns_theta_full        30.55
_diffrn_reflns_theta_max         30.55
_diffrn_reflns_theta_min         1.53
_exptl_absorpt_coefficient_mu    0.102
_exptl_absorpt_correction_T_max  0.9919
_exptl_absorpt_correction_T_min  0.9769
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.372
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             808
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.358
_refine_diff_density_min         -0.319
_refine_diff_density_rms         0.042
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     330
_refine_ls_number_reflns         5783
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.031
_refine_ls_R_factor_all          0.0983
_refine_ls_R_factor_gt           0.0540
_refine_ls_shift/su_max          0.019
_refine_ls_shift/su_mean         0.003
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0703P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1270
_refine_ls_wR_factor_ref         0.1443
_reflns_number_gt                3516
_reflns_number_total             5783
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo0705420si20070315_044550_4.cif
_cod_data_source_block           BORAZAN6
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               4024060
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
F1 F 1.03757(11) 0.38236(8) 0.24811(15) 0.0763(4) Uani 1 1 d . . .
F2 F 1.06252(12) 0.39953(9) 0.47175(16) 0.0840(5) Uani 1 1 d . . .
F3 F 0.92170(10) 0.43440(8) 0.36942(19) 0.0925(5) Uani 1 1 d . . .
N1 N 0.70940(9) 0.09573(8) 0.60175(13) 0.0284(3) Uani 1 1 d . . .
N2 N 0.75435(9) 0.17562(8) 0.59443(13) 0.0290(3) Uani 1 1 d . . .
N3 N 0.85240(10) 0.03205(8) 0.48477(14) 0.0319(3) Uani 1 1 d . . .
B1 B 0.73822(13) 0.01976(11) 0.49221(18) 0.0289(4) Uani 1 1 d . . .
C1 C 0.63578(12) 0.10333(11) 0.69274(16) 0.0334(3) Uani 1 1 d . . .
C2 C 0.63273(14) 0.18814(11) 0.74525(18) 0.0388(4) Uani 1 1 d . . .
C3 C 0.70834(13) 0.23208(11) 0.68150(17) 0.0354(4) Uani 1 1 d . . .
C4 C 0.83827(11) 0.18798(9) 0.50636(16) 0.0296(3) Uani 1 1 d . . .
C5 C 0.87078(12) 0.27226(10) 0.47892(17) 0.0340(3) Uani 1 1 d . . .
C6 C 0.95522(12) 0.28459(11) 0.39958(19) 0.0385(4) Uani 1 1 d . . .
C7 C 1.00607(13) 0.21242(12) 0.3487(2) 0.0439(4) Uani 1 1 d . . .
C8 C 0.97319(12) 0.12858(11) 0.3752(2) 0.0400(4) Uani 1 1 d . . .
C9 C 0.88785(11) 0.11361(10) 0.45527(16) 0.0305(3) Uani 1 1 d . . .
C10 C 0.99329(14) 0.37410(12) 0.3740(2) 0.0493(5) Uani 1 1 d . . .
C11 C 0.67942(11) 0.04068(9) 0.33995(15) 0.0280(3) Uani 1 1 d . . .
C12 C 0.72234(13) 0.02001(11) 0.20965(17) 0.0371(4) Uani 1 1 d . . .
C13 C 0.67239(15) 0.03554(12) 0.07784(18) 0.0433(4) Uani 1 1 d . . .
C14 C 0.57763(14) 0.07237(11) 0.07205(19) 0.0404(4) Uani 1 1 d . . .
C15 C 0.53262(13) 0.09316(11) 0.19864(18) 0.0380(4) Uani 1 1 d . . .
C16 C 0.58302(12) 0.07739(10) 0.32963(17) 0.0324(3) Uani 1 1 d . . .
C17 C 0.71123(11) -0.07374(10) 0.56158(16) 0.0320(3) Uani 1 1 d . . .
C18 C 0.75611(13) -0.10078(12) 0.69279(19) 0.0393(4) Uani 1 1 d . . .
C19 C 0.73820(15) -0.18336(13) 0.7489(2) 0.0500(5) Uani 1 1 d . . .
C20 C 0.67497(17) -0.24073(13) 0.6740(2) 0.0564(6) Uani 1 1 d . . .
C21 C 0.62785(18) -0.21552(12) 0.5465(2) 0.0528(5) Uani 1 1 d . . .
C22 C 0.64511(14) -0.13213(10) 0.49123(19) 0.0393(4) Uani 1 1 d . . .
H3N H 0.8891(14) -0.0119(11) 0.4491(18) 0.040(5) Uiso 1 1 d . . .
H1 H 0.5960(12) 0.0554(11) 0.7110(17) 0.034(4) Uiso 1 1 d . . .
H2 H 0.5868(13) 0.2119(11) 0.8139(19) 0.045(5) Uiso 1 1 d . . .
H3 H 0.7325(13) 0.2910(12) 0.6935(19) 0.041(5) Uiso 1 1 d . . .
H5 H 0.8356(12) 0.3214(11) 0.5159(17) 0.033(4) Uiso 1 1 d . . .
H7 H 1.0636(15) 0.2190(12) 0.292(2) 0.047(5) Uiso 1 1 d . . .
H8 H 1.0070(16) 0.0791(14) 0.337(2) 0.063(6) Uiso 1 1 d . . .
H12 H 0.7920(15) -0.0047(12) 0.212(2) 0.051(5) Uiso 1 1 d . . .
H13 H 0.7019(17) 0.0196(14) -0.009(2) 0.069(6) Uiso 1 1 d . . .
H14 H 0.5420(13) 0.0850(11) -0.019(2) 0.039(5) Uiso 1 1 d . . .
H15 H 0.4639(15) 0.1213(12) 0.193(2) 0.050(5) Uiso 1 1 d . . .
H16 H 0.5500(14) 0.0935(11) 0.417(2) 0.045(5) Uiso 1 1 d . . .
H18 H 0.8059(14) -0.0610(12) 0.7485(18) 0.044(5) Uiso 1 1 d . . .
H19 H 0.7705(16) -0.2017(14) 0.834(2) 0.058(6) Uiso 1 1 d . . .
H20 H 0.6645(15) -0.2967(14) 0.715(2) 0.058(6) Uiso 1 1 d . . .
H21 H 0.5813(17) -0.2547(15) 0.491(2) 0.070(7) Uiso 1 1 d . . .
H22 H 0.6122(13) -0.1112(12) 0.401(2) 0.046(5) Uiso 1 1 d . . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
B B 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 N1 N2 106.97(12) . . ?
C1 N1 B1 132.33(13) . . ?
N2 N1 B1 119.89(11) . . ?
C3 N2 N1 109.28(12) . . ?
C3 N2 C4 130.44(13) . . ?
N1 N2 C4 120.26(11) . . ?
C9 N3 B1 118.19(12) . . ?
C9 N3 H3N 114.0(11) . . ?
B1 N3 H3N 118.6(11) . . ?
N3 B1 N1 101.87(12) . . ?
N3 B1 C17 111.37(12) . . ?
N1 B1 C17 108.76(11) . . ?
N3 B1 C11 112.12(12) . . ?
N1 B1 C11 107.12(11) . . ?
C17 B1 C11 114.66(13) . . ?
N1 C1 C2 109.92(15) . . ?
N1 C1 H1 119.6(10) . . ?
C2 C1 H1 130.5(10) . . ?
C3 C2 C1 105.77(15) . . ?
C3 C2 H2 126.7(10) . . ?
C1 C2 H2 127.6(10) . . ?
N2 C3 C2 108.06(15) . . ?
N2 C3 H3 120.7(11) . . ?
C2 C3 H3 131.2(11) . . ?
C5 C4 C9 122.17(14) . . ?
C5 C4 N2 119.19(13) . . ?
C9 C4 N2 118.58(13) . . ?
C6 C5 C4 119.49(15) . . ?
C6 C5 H5 120.5(10) . . ?
C4 C5 H5 120.0(10) . . ?
C5 C6 C7 119.60(15) . . ?
C5 C6 C10 120.20(16) . . ?
C7 C6 C10 120.16(16) . . ?
C8 C7 C6 120.84(16) . . ?
C8 C7 H7 117.8(11) . . ?
C6 C7 H7 121.3(11) . . ?
C7 C8 C9 121.11(16) . . ?
C7 C8 H8 120.5(13) . . ?
C9 C8 H8 118.4(13) . . ?
N3 C9 C8 123.41(14) . . ?
N3 C9 C4 119.81(13) . . ?
C8 C9 C4 116.78(14) . . ?
F2 C10 F3 107.19(18) . . ?
F2 C10 F1 104.72(16) . . ?
F3 C10 F1 104.48(17) . . ?
F2 C10 C6 113.12(16) . . ?
F3 C10 C6 113.34(15) . . ?
F1 C10 C6 113.23(16) . . ?
C16 C11 C12 116.04(14) . . ?
C16 C11 B1 122.98(13) . . ?
C12 C11 B1 120.95(14) . . ?
C13 C12 C11 121.97(16) . . ?
C13 C12 H12 119.4(11) . . ?
C11 C12 H12 118.5(11) . . ?
C14 C13 C12 120.28(16) . . ?
C14 C13 H13 119.1(13) . . ?
C12 C13 H13 120.6(14) . . ?
C13 C14 C15 119.35(16) . . ?
C13 C14 H14 121.6(10) . . ?
C15 C14 H14 119.1(10) . . ?
C14 C15 C16 119.96(16) . . ?
C14 C15 H15 118.4(11) . . ?
C16 C15 H15 121.6(11) . . ?
C15 C16 C11 122.40(15) . . ?
C15 C16 H16 118.1(11) . . ?
C11 C16 H16 119.5(11) . . ?
C22 C17 C18 117.22(15) . . ?
C22 C17 B1 121.61(14) . . ?
C18 C17 B1 121.13(14) . . ?
C19 C18 C17 121.52(18) . . ?
C19 C18 H18 117.8(10) . . ?
C17 C18 H18 120.6(10) . . ?
C20 C19 C18 119.77(19) . . ?
C20 C19 H19 119.2(13) . . ?
C18 C19 H19 120.9(13) . . ?
C21 C20 C19 120.19(18) . . ?
C21 C20 H20 122.1(12) . . ?
C19 C20 H20 117.7(12) . . ?
C20 C21 C22 119.9(2) . . ?
C20 C21 H21 122.2(13) . . ?
C22 C21 H21 117.9(13) . . ?
C17 C22 C21 121.36(18) . . ?
C17 C22 H22 116.1(11) . . ?
C21 C22 H22 122.5(11) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
F1 C10 1.342(2) . ?
F2 C10 1.325(2) . ?
F3 C10 1.325(2) . ?
N1 C1 1.3296(19) . ?
N1 N2 1.3625(17) . ?
N1 B1 1.604(2) . ?
N2 C3 1.3501(19) . ?
N2 C4 1.4283(19) . ?
N3 C9 1.3649(19) . ?
N3 B1 1.536(2) . ?
N3 H3N 0.903(18) . ?
B1 C17 1.615(2) . ?
B1 C11 1.621(2) . ?
C1 C2 1.386(2) . ?
C1 H1 0.924(17) . ?
C2 C3 1.368(2) . ?
C2 H2 0.975(18) . ?
C3 H3 0.961(18) . ?
C4 C5 1.386(2) . ?
C4 C9 1.408(2) . ?
C5 C6 1.386(2) . ?
C5 H5 0.957(16) . ?
C6 C7 1.389(2) . ?
C6 C10 1.482(2) . ?
C7 C8 1.380(2) . ?
C7 H7 0.95(2) . ?
C8 C9 1.406(2) . ?
C8 H8 0.96(2) . ?
C11 C16 1.400(2) . ?
C11 C12 1.401(2) . ?
C12 C13 1.391(2) . ?
C12 H12 1.001(19) . ?
C13 C14 1.380(3) . ?
C13 H13 0.94(2) . ?
C14 C15 1.384(2) . ?
C14 H14 0.974(18) . ?
C15 C16 1.387(2) . ?
C15 H15 1.01(2) . ?
C16 H16 0.973(18) . ?
C17 C22 1.396(2) . ?
C17 C18 1.399(2) . ?
C18 C19 1.390(2) . ?
C18 H18 1.023(18) . ?
C19 C20 1.383(3) . ?
C19 H19 0.93(2) . ?
C20 C21 1.374(3) . ?
C20 H20 0.95(2) . ?
C21 C22 1.397(2) . ?
C21 H21 0.99(2) . ?
C22 H22 0.987(19) . ?
