#------------------------------------------------------------------------------
#$Date: 2016-03-21 03:04:54 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178419 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/40/4024059.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_4024059
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'
_chemical_formula_weight         337.22
_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   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 97.4950(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   12.7082(12)
_cell_length_b                   15.4722(14)
_cell_length_c                   9.3613(9)
_cell_measurement_reflns_used    4782
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      31
_cell_measurement_theta_min      2.5
_cell_volume                     1824.9(3)
_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 0.932
_diffrn_measured_fraction_theta_max 0.932
_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  0.0208
_diffrn_reflns_av_sigmaI/netI    0.0260
_diffrn_reflns_limit_h_max       18
_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            14988
_diffrn_reflns_theta_full        31.89
_diffrn_reflns_theta_max         31.89
_diffrn_reflns_theta_min         2.08
_exptl_absorpt_coefficient_mu    0.073
_exptl_absorpt_correction_T_max  0.9856
_exptl_absorpt_correction_T_min  0.9751
_exptl_absorpt_correction_type   'semi-empirical (SADABS procedure)'
_exptl_crystal_colour            reddish-brown
_exptl_crystal_density_diffrn    1.227
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             712
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.366
_refine_diff_density_min         -0.240
_refine_diff_density_rms         0.046
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.068
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     315
_refine_ls_number_reflns         5842
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.068
_refine_ls_R_factor_all          0.0624
_refine_ls_R_factor_gt           0.0468
_refine_ls_shift/su_max          0.060
_refine_ls_shift/su_mean         0.003
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0868P)²+0.0375P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1281
_refine_ls_wR_factor_ref         0.1390
_reflns_number_gt                4491
_reflns_number_total             5842
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo0705420si20070315_044550_3.cif
_cod_data_source_block           BORAZAN2
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               4024059
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
N1 N 0.71487(6) 0.09743(5) 0.63146(9) 0.02178(17) Uani 1 1 d . . .
N2 N 0.75619(6) 0.17847(5) 0.62985(9) 0.02227(17) Uani 1 1 d . . .
N3 N 0.86659(6) 0.04352(5) 0.52341(9) 0.02314(17) Uani 1 1 d . . .
B1 B 0.74775(8) 0.02512(7) 0.52322(11) 0.0217(2) Uani 1 1 d . . .
C1 C 0.63749(8) 0.10022(7) 0.71536(11) 0.0267(2) Uani 1 1 d . . .
C2 C 0.62898(9) 0.18352(7) 0.76840(12) 0.0307(2) Uani 1 1 d . . .
C3 C 0.70511(8) 0.23139(7) 0.71292(11) 0.0278(2) Uani 1 1 d . . .
C4 C 0.84023(7) 0.19693(6) 0.54729(10) 0.02173(19) Uani 1 1 d . . .
C5 C 0.86663(8) 0.28270(7) 0.52335(11) 0.0261(2) Uani 1 1 d . . .
C6 C 0.94885(8) 0.30245(7) 0.44473(12) 0.0289(2) Uani 1 1 d . . .
C7 C 1.00298(8) 0.23411(7) 0.39053(12) 0.0302(2) Uani 1 1 d . . .
C8 C 0.97668(8) 0.14905(7) 0.41323(12) 0.0279(2) Uani 1 1 d . . .
C9 C 0.89454(7) 0.12772(6) 0.49387(10) 0.02234(19) Uani 1 1 d . . .
C10 C 0.97696(11) 0.39475(8) 0.41639(17) 0.0402(3) Uani 1 1 d . . .
C11 C 0.67981(7) 0.04413(6) 0.36687(10) 0.02199(19) Uani 1 1 d . . .
C12 C 0.72053(9) 0.02034(7) 0.24002(11) 0.0294(2) Uani 1 1 d . . .
C13 C 0.66496(9) 0.03562(8) 0.10409(12) 0.0338(2) Uani 1 1 d . . .
C14 C 0.56681(9) 0.07581(8) 0.09107(12) 0.0321(2) Uani 1 1 d . . .
C15 C 0.52383(8) 0.09926(7) 0.21342(12) 0.0300(2) Uani 1 1 d . . .
C16 C 0.58015(8) 0.08353(7) 0.34932(11) 0.0257(2) Uani 1 1 d . . .
C17 C 0.72840(7) -0.06900(6) 0.58876(10) 0.02315(19) Uani 1 1 d . . .
C18 C 0.77926(8) -0.09330(7) 0.72504(12) 0.0282(2) Uani 1 1 d . . .
C19 C 0.76832(9) -0.17582(8) 0.78042(13) 0.0340(2) Uani 1 1 d . . .
C20 C 0.70626(10) -0.23694(8) 0.70055(14) 0.0367(3) Uani 1 1 d . . .
C21 C 0.65380(10) -0.21436(7) 0.56611(13) 0.0350(3) Uani 1 1 d . . .
C22 C 0.66429(9) -0.13135(7) 0.51238(11) 0.0283(2) Uani 1 1 d . . .
H3N H 0.9013(11) 0.0040(9) 0.4767(15) 0.038(4) Uiso 1 1 d . . .
H1 H 0.5968(11) 0.0505(9) 0.7315(14) 0.033(3) Uiso 1 1 d . . .
H2 H 0.5811(11) 0.2044(9) 0.8291(15) 0.040(4) Uiso 1 1 d . . .
H3 H 0.7275(11) 0.2897(10) 0.7283(16) 0.040(4) Uiso 1 1 d . . .
H5 H 0.8267(11) 0.3289(9) 0.5632(15) 0.037(4) Uiso 1 1 d . . .
H7 H 1.0593(12) 0.2480(10) 0.3337(16) 0.043(4) Uiso 1 1 d . . .
H8 H 1.0152(12) 0.1034(10) 0.3698(15) 0.040(4) Uiso 1 1 d . . .
H10A H 1.0531(19) 0.4062(15) 0.445(2) 0.091(7) Uiso 1 1 d . . .
H10B H 0.9596(16) 0.4155(12) 0.313(2) 0.079(6) Uiso 1 1 d . . .
H10C H 0.9395(19) 0.4325(14) 0.474(2) 0.092(7) Uiso 1 1 d . . .
H12 H 0.7904(11) -0.0066(9) 0.2473(15) 0.041(4) Uiso 1 1 d . . .
H13 H 0.7007(13) 0.0163(10) 0.0197(18) 0.055(4) Uiso 1 1 d . . .
H14 H 0.5303(11) 0.0885(9) -0.0029(15) 0.036(3) Uiso 1 1 d . . .
H15 H 0.4544(11) 0.1289(9) 0.2062(14) 0.034(3) Uiso 1 1 d . . .
H16 H 0.5455(11) 0.1030(9) 0.4336(15) 0.034(3) Uiso 1 1 d . . .
H18 H 0.8240(11) -0.0505(9) 0.7864(14) 0.032(3) Uiso 1 1 d . . .
H19 H 0.8036(12) -0.1930(10) 0.8769(17) 0.047(4) Uiso 1 1 d . . .
H20 H 0.6972(11) -0.2960(10) 0.7372(16) 0.045(4) Uiso 1 1 d . . .
H21 H 0.6119(12) -0.2592(11) 0.5058(17) 0.048(4) Uiso 1 1 d . . .
H22 H 0.6279(11) -0.1149(9) 0.4170(15) 0.036(3) 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'
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 106.94(8) . . ?
C1 N1 B1 131.84(8) . . ?
N2 N1 B1 120.27(7) . . ?
C3 N2 N1 109.69(8) . . ?
C3 N2 C4 129.78(9) . . ?
N1 N2 C4 120.53(8) . . ?
C9 N3 B1 116.79(8) . . ?
N3 B1 N1 101.97(8) . . ?
N3 B1 C17 111.46(8) . . ?
N1 B1 C17 108.97(7) . . ?
N3 B1 C11 111.96(8) . . ?
N1 B1 C11 106.95(7) . . ?
C17 B1 C11 114.62(8) . . ?
N1 C1 C2 109.70(9) . . ?
C3 C2 C1 105.87(9) . . ?
N2 C3 C2 107.80(10) . . ?
C5 C4 C9 122.01(9) . . ?
C5 C4 N2 119.38(8) . . ?
C9 C4 N2 118.61(8) . . ?
C6 C5 C4 120.55(10) . . ?
C5 C6 C7 117.88(10) . . ?
C5 C6 C10 121.00(11) . . ?
C7 C6 C10 121.11(10) . . ?
C8 C7 C6 121.77(10) . . ?
C7 C8 C9 121.21(10) . . ?
N3 C9 C4 119.71(9) . . ?
N3 C9 C8 123.71(9) . . ?
C4 C9 C8 116.58(9) . . ?
C16 C11 C12 116.33(9) . . ?
C16 C11 B1 123.50(8) . . ?
C12 C11 B1 120.17(8) . . ?
C13 C12 C11 121.94(10) . . ?
C14 C13 C12 120.02(10) . . ?
C15 C14 C13 119.63(10) . . ?
C14 C15 C16 119.90(10) . . ?
C11 C16 C15 122.17(10) . . ?
C22 C17 C18 116.65(9) . . ?
C22 C17 B1 122.46(9) . . ?
C18 C17 B1 120.86(9) . . ?
C19 C18 C17 121.84(10) . . ?
C20 C19 C18 120.16(11) . . ?
C19 C20 C21 119.27(11) . . ?
C20 C21 C22 120.13(11) . . ?
C21 C22 C17 121.93(10) . . ?
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
N1 C1 1.3369(12) . ?
N1 N2 1.3602(11) . ?
N1 B1 1.6011(13) . ?
N2 C3 1.3521(13) . ?
N2 C4 1.4265(12) . ?
N3 C9 1.3876(12) . ?
N3 B1 1.5366(13) . ?
B1 C17 1.6115(15) . ?
B1 C11 1.6262(14) . ?
C1 C2 1.3904(15) . ?
C2 C3 1.3730(16) . ?
C4 C5 1.3942(14) . ?
C4 C9 1.4011(13) . ?
C5 C6 1.3883(15) . ?
C6 C7 1.3927(16) . ?
C6 C10 1.5040(16) . ?
C7 C8 1.3811(15) . ?
C8 C9 1.4049(13) . ?
C11 C16 1.3958(14) . ?
C11 C12 1.4049(14) . ?
C12 C13 1.3926(15) . ?
C13 C14 1.3848(17) . ?
C14 C15 1.3802(17) . ?
C15 C16 1.3974(14) . ?
C17 C22 1.3977(14) . ?
C17 C18 1.4041(14) . ?
C18 C19 1.3917(15) . ?
C19 C20 1.3863(18) . ?
C20 C21 1.3898(18) . ?
C21 C22 1.3921(15) . ?
