#------------------------------------------------------------------------------
#$Date: 2016-03-21 03:04:54 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178419 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/40/4024058.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_4024058
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 H20 B N3 O'
_chemical_formula_weight         353.22
_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   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/[σ²(Fo²)+(0.0815P)²+0.0812P] where P=(Fo²+2Fc²)/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
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
O1 O 0.46207(8) 0.39905(5) 0.94218(11) 0.0379(2) Uani 1 1 d . . .
N1 N 0.21794(7) 0.09544(5) 1.13842(10) 0.01932(18) Uani 1 1 d . . .
N2 N 0.25905(7) 0.17902(5) 1.14001(10) 0.01917(18) Uani 1 1 d . . .
N3 N 0.36827(7) 0.04375(6) 1.02812(10) 0.02035(19) Uani 1 1 d . . .
B1 B 0.24870(9) 0.02355(7) 1.02969(13) 0.0187(2) Uani 1 1 d . . .
C1 C 0.14335(9) 0.09564(7) 1.22269(12) 0.0232(2) Uani 1 1 d . . .
C2 C 0.13596(10) 0.17987(7) 1.27921(13) 0.0269(2) Uani 1 1 d . . .
C3 C 0.21038(9) 0.23094(7) 1.22561(12) 0.0241(2) Uani 1 1 d . . .
C4 C 0.34022(7) 0.20045(6) 1.05771(11) 0.0185(2) Uani 1 1 d . . .
C5 C 0.36449(8) 0.28889(7) 1.03707(12) 0.0228(2) Uani 1 1 d . . .
C6 C 0.44417(9) 0.30997(7) 0.95834(13) 0.0247(2) Uani 1 1 d . . .
C7 C 0.49855(8) 0.24291(7) 0.89980(13) 0.0246(2) Uani 1 1 d . . .
C8 C 0.47275(8) 0.15503(7) 0.92077(12) 0.0229(2) Uani 1 1 d . . .
C9 C 0.39420(7) 0.13079(6) 1.00053(11) 0.0185(2) Uani 1 1 d . . .
C10 C 0.54455(10) 0.42292(8) 0.86394(15) 0.0319(3) Uani 1 1 d . . .
C11 C 0.17593(8) 0.04394(6) 0.87791(11) 0.0189(2) Uani 1 1 d . . .
C12 C 0.21282(9) 0.01795(7) 0.75444(12) 0.0250(2) Uani 1 1 d . . .
C13 C 0.15498(10) 0.03469(8) 0.62143(13) 0.0288(2) Uani 1 1 d . . .
C14 C 0.05704(9) 0.07897(7) 0.60911(13) 0.0276(2) Uani 1 1 d . . .
C15 C 0.01790(9) 0.10508(7) 0.72895(13) 0.0260(2) Uani 1 1 d . . .
C16 C 0.07663(8) 0.08750(7) 0.86150(13) 0.0226(2) Uani 1 1 d . . .
C17 C 0.23326(8) -0.07400(6) 1.09188(12) 0.0200(2) Uani 1 1 d . . .
C18 C 0.28739(9) -0.09868(7) 1.22484(13) 0.0251(2) Uani 1 1 d . . .
C19 C 0.27974(10) -0.18381(8) 1.27745(14) 0.0301(3) Uani 1 1 d . . .
C20 C 0.21756(10) -0.24738(8) 1.19801(14) 0.0327(3) Uani 1 1 d . . .
C21 C 0.16266(10) -0.22472(7) 1.06699(14) 0.0310(3) Uani 1 1 d . . .
C22 C 0.16992(9) -0.13870(7) 1.01532(13) 0.0241(2) Uani 1 1 d . . .
H3N H 0.4025(11) 0.0060(10) 0.9809(15) 0.027(3) Uiso 1 1 d . . .
H1 H 0.1030(11) 0.0428(9) 1.2362(15) 0.027(3) Uiso 1 1 d . . .
H2 H 0.0898(12) 0.2004(10) 1.3434(16) 0.034(4) Uiso 1 1 d . . .
H3 H 0.2328(11) 0.2923(9) 1.2424(15) 0.029(3) Uiso 1 1 d . . .
H5 H 0.3267(12) 0.3345(9) 1.0766(16) 0.031(4) Uiso 1 1 d . . .
H7 H 0.5511(12) 0.2578(10) 0.8407(15) 0.034(4) Uiso 1 1 d . . .
H8 H 0.5110(12) 0.1086(10) 0.8775(15) 0.032(4) Uiso 1 1 d . . .
H10A H 0.5456(13) 0.4887(11) 0.8635(17) 0.044(4) Uiso 1 1 d . . .
H10B H 0.5304(13) 0.4019(10) 0.7659(18) 0.039(4) Uiso 1 1 d . . .
H10C H 0.6156(13) 0.3981(10) 0.9096(16) 0.038(4) Uiso 1 1 d . . .
H12 H 0.2828(12) -0.0130(9) 0.7607(16) 0.032(4) Uiso 1 1 d . . .
H13 H 0.1843(12) 0.0136(11) 0.5419(18) 0.040(4) Uiso 1 1 d . . .
H14 H 0.0168(12) 0.0920(10) 0.5156(16) 0.036(4) Uiso 1 1 d . . .
H15 H -0.0507(13) 0.1355(9) 0.7225(16) 0.033(4) Uiso 1 1 d . . .
H16 H 0.0448(12) 0.1069(9) 0.9447(16) 0.029(3) Uiso 1 1 d . . .
H18 H 0.3323(11) -0.0536(10) 1.2831(15) 0.032(4) Uiso 1 1 d . . .
H19 H 0.3172(12) -0.1996(10) 1.3720(17) 0.038(4) Uiso 1 1 d . . .
H20 H 0.2126(13) -0.3073(11) 1.2341(18) 0.047(4) Uiso 1 1 d . . .
H21 H 0.1198(11) -0.2687(10) 1.0107(16) 0.034(4) Uiso 1 1 d . . .
H22 H 0.1304(12) -0.1230(9) 0.9197(16) 0.030(4) 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'
O O 0.0106 0.0060 '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
C6 O1 C10 116.98(9) . . ?
C1 N1 N2 107.04(8) . . ?
C1 N1 B1 131.77(8) . . ?
N2 N1 B1 120.42(8) . . ?
C3 N2 N1 109.67(8) . . ?
C3 N2 C4 129.80(8) . . ?
N1 N2 C4 120.53(8) . . ?
C9 N3 B1 116.66(8) . . ?
C9 N3 H3N 111.4(9) . . ?
B1 N3 H3N 115.7(9) . . ?
N3 B1 N1 102.07(8) . . ?
N3 B1 C17 111.06(8) . . ?
N1 B1 C17 108.77(8) . . ?
N3 B1 C11 111.59(9) . . ?
N1 B1 C11 107.46(8) . . ?
C17 B1 C11 114.98(8) . . ?
N1 C1 C2 109.65(9) . . ?
N1 C1 H1 121.0(9) . . ?
C2 C1 H1 129.4(9) . . ?
C3 C2 C1 105.95(10) . . ?
C3 C2 H2 125.1(9) . . ?
C1 C2 H2 129.0(9) . . ?
N2 C3 C2 107.68(9) . . ?
N2 C3 H3 120.4(8) . . ?
C2 C3 H3 131.9(8) . . ?
C5 C4 C9 122.04(10) . . ?
C5 C4 N2 119.34(9) . . ?
C9 C4 N2 118.61(8) . . ?
C6 C5 C4 119.51(10) . . ?
C6 C5 H5 120.2(9) . . ?
C4 C5 H5 120.3(9) . . ?
O1 C6 C5 115.57(10) . . ?
O1 C6 C7 124.50(10) . . ?
C5 C6 C7 119.92(10) . . ?
C8 C7 C6 119.75(10) . . ?
C8 C7 H7 120.4(9) . . ?
C6 C7 H7 119.7(9) . . ?
C7 C8 C9 122.28(10) . . ?
C7 C8 H8 118.7(9) . . ?
C9 C8 H8 119.0(9) . . ?
N3 C9 C8 124.22(9) . . ?
N3 C9 C4 119.28(9) . . ?
C8 C9 C4 116.49(9) . . ?
O1 C10 H10A 105.5(10) . . ?
O1 C10 H10B 112.9(9) . . ?
H10A C10 H10B 108.5(13) . . ?
O1 C10 H10C 110.3(9) . . ?
H10A C10 H10C 111.3(13) . . ?
H10B C10 H10C 108.4(13) . . ?
C12 C11 C16 116.42(10) . . ?
C12 C11 B1 119.69(9) . . ?
C16 C11 B1 123.89(10) . . ?
C13 C12 C11 122.36(10) . . ?
C13 C12 H12 118.3(9) . . ?
C11 C12 H12 119.4(9) . . ?
C14 C13 C12 119.63(11) . . ?
C14 C13 H13 122.7(10) . . ?
C12 C13 H13 117.7(10) . . ?
C15 C14 C13 119.52(11) . . ?
C15 C14 H14 120.6(9) . . ?
C13 C14 H14 119.9(9) . . ?
C14 C15 C16 120.15(10) . . ?
C14 C15 H15 120.7(9) . . ?
C16 C15 H15 119.1(9) . . ?
C15 C16 C11 121.91(11) . . ?
C15 C16 H16 117.2(8) . . ?
C11 C16 H16 120.9(8) . . ?
C22 C17 C18 116.85(9) . . ?
C22 C17 B1 122.32(10) . . ?
C18 C17 B1 120.77(9) . . ?
C19 C18 C17 121.76(11) . . ?
C19 C18 H18 119.4(8) . . ?
C17 C18 H18 118.9(8) . . ?
C20 C19 C18 120.19(12) . . ?
C20 C19 H19 119.2(9) . . ?
C18 C19 H19 120.6(9) . . ?
C21 C20 C19 119.30(11) . . ?
C21 C20 H20 120.3(10) . . ?
C19 C20 H20 120.4(10) . . ?
C20 C21 C22 120.19(11) . . ?
C20 C21 H21 119.8(9) . . ?
C22 C21 H21 120.0(9) . . ?
C17 C22 C21 121.69(11) . . ?
C17 C22 H22 118.7(8) . . ?
C21 C22 H22 119.6(8) . . ?
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
O1 C6 1.3766(13) . ?
O1 C10 1.4207(14) . ?
N1 C1 1.3330(14) . ?
N1 N2 1.3631(11) . ?
N1 B1 1.5969(14) . ?
N2 C3 1.3514(13) . ?
N2 C4 1.4241(13) . ?
N3 C9 1.3895(12) . ?
N3 B1 1.5378(14) . ?
N3 H3N 0.883(15) . ?
B1 C17 1.6130(15) . ?
B1 C11 1.6286(16) . ?
C1 C2 1.3922(15) . ?
C1 H1 0.966(14) . ?
C2 C3 1.3744(16) . ?
C2 H2 0.963(15) . ?
C3 H3 0.974(14) . ?
C4 C5 1.3910(14) . ?
C4 C9 1.4098(14) . ?
C5 C6 1.3851(16) . ?
C5 H5 0.949(15) . ?
C6 C7 1.3898(15) . ?
C7 C8 1.3882(15) . ?
C7 H7 0.964(15) . ?
C8 C9 1.3919(15) . ?
C8 H8 0.980(15) . ?
C10 H10A 0.993(17) . ?
C10 H10B 0.986(17) . ?
C10 H10C 1.006(15) . ?
C11 C12 1.3981(16) . ?
C11 C16 1.3991(14) . ?
C12 C13 1.3941(17) . ?
C12 H12 0.990(14) . ?
C13 C14 1.3909(17) . ?
C13 H13 0.955(17) . ?
C14 C15 1.3809(18) . ?
C14 H14 0.981(15) . ?
C15 C16 1.3972(16) . ?
C15 H15 0.971(15) . ?
C16 H16 0.994(15) . ?
C17 C22 1.3965(15) . ?
C17 C18 1.4037(16) . ?
C18 C19 1.3904(15) . ?
C18 H18 0.999(15) . ?
C19 C20 1.3900(19) . ?
C19 H19 0.987(16) . ?
C20 C21 1.3836(19) . ?
C20 H20 0.975(17) . ?
C21 C22 1.3989(15) . ?
C21 H21 0.967(15) . ?
C22 H22 1.004(15) . ?
