#------------------------------------------------------------------------------
#$Date: 2017-10-13 09:09:21 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201973 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/20/94/2209457.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2209457
loop_
_publ_author_name
'Xia, Min'
'Ge, Shao-Qin'
'Li, Xiang-Sheng'
_publ_section_title
;
 Difluoro[1-(1-naphthyliminomethyl)-2-naphtholato-N,O]boron
;
_journal_coeditor_code           CV2059
_journal_issue                   7
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2625
_journal_page_last               o2626
_journal_paper_doi               10.1107/S160053680602068X
_journal_volume                  62
_journal_year                    2006
_chemical_formula_iupac          'C21 H14 B F2 N O'
_chemical_formula_moiety         'C21 H14 B F2 N O'
_chemical_formula_sum            'C21 H14 B F2 N O'
_chemical_formula_weight         345.14
_chemical_name_systematic
;
Difluoro[1-(1-naphthyliminomethyl)-2-naphtholato-N,O]boron
;
_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                 92.28(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.195(2)
_cell_length_b                   15.524(3)
_cell_length_c                   10.498(2)
_cell_measurement_reflns_used    10717
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.50
_cell_measurement_theta_min      3.03
_cell_volume                     1660.2(6)
_computing_cell_refinement       RAPID-AUTO
_computing_data_collection       'RAPID-AUTO (Rigaku, 1998)'
_computing_data_reduction        'CrystalStructure (Rigaku/MSC, 2002)'
_computing_molecular_graphics    'ORTEP-3 (Farrugia, 1997)'
_computing_publication_material  SHELXL97
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      294(2)
_diffrn_detector_area_resol_mean 10.00
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type  'Rigaku R-AXIS RAPID'
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71069
_diffrn_reflns_av_R_equivalents  0.0326
_diffrn_reflns_av_sigmaI/netI    0.0291
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            15916
_diffrn_reflns_theta_full        27.48
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_min         3.03
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.099
_exptl_absorpt_correction_T_max  0.990
_exptl_absorpt_correction_T_min  0.956
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(ABSCOR; Higashi, 1995)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.381
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             712
_exptl_crystal_size_max          0.33
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.312
_refine_diff_density_min         -0.215
_refine_ls_extinction_coef       0.0083(14)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL97
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     236
_refine_ls_number_reflns         3771
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.057
_refine_ls_R_factor_all          0.0758
_refine_ls_R_factor_gt           0.0438
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0546P)²+0.1252P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1097
_refine_ls_wR_factor_ref         0.1217
_reflns_number_gt                2321
_reflns_number_total             3771
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            cv2059.cif
_cod_data_source_block           I
_cod_original_cell_volume        1660.1(6)
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2209457
_cod_database_fobs_code          2209457
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_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
F F1 0.37990(13) 0.10032(8) 0.57731(13) 0.1043(5) Uani d . 1
F F2 0.24590(13) 0.13442(9) 0.73234(11) 0.1052(5) Uani d . 1
O O1 0.41056(11) 0.22748(8) 0.68302(12) 0.0675(4) Uani d . 1
N N1 0.21809(11) 0.20983(8) 0.53627(11) 0.0446(3) Uani d . 1
C C1 0.21891(14) 0.29238(10) 0.51743(13) 0.0441(3) Uani d . 1
H H1 0.1575 0.3158 0.4594 0.053 Uiso calc R 1
C C2 0.30913(14) 0.34851(10) 0.58124(13) 0.0446(4) Uani d . 1
C C3 0.30416(15) 0.44055(10) 0.56484(13) 0.0490(4) Uani d . 1
C C4 0.20953(18) 0.48360(11) 0.48811(15) 0.0603(4) Uani d . 1
H H4 0.1460 0.4519 0.4426 0.072 Uiso calc R 1
C C5 0.2091(2) 0.57121(12) 0.47916(17) 0.0760(6) Uani d . 1
H H5 0.1444 0.5985 0.4289 0.091 Uiso calc R 1
C C6 0.3042(3) 0.62040(13) 0.54411(19) 0.0848(7) Uani d . 1
H H6 0.3035 0.6801 0.5363 0.102 Uiso calc R 1
C C7 0.3977(2) 0.58127(13) 0.61860(18) 0.0749(6) Uani d . 1
H H7 0.4614 0.6144 0.6614 0.090 Uiso calc R 1
C C8 0.39985(17) 0.49123(11) 0.63224(15) 0.0570(4) Uani d . 1
C C9 0.49431(18) 0.44972(13) 0.71272(18) 0.0684(5) Uani d . 1
H H9 0.5572 0.4832 0.7561 0.082 Uiso calc R 1
C C10 0.49716(17) 0.36380(13) 0.72937(18) 0.0667(5) Uani d . 1
H H10 0.5603 0.3389 0.7842 0.080 Uiso calc R 1
C C11 0.40405(15) 0.31182(11) 0.66341(15) 0.0522(4) Uani d . 1
C C12 0.11761(14) 0.15780(9) 0.47251(13) 0.0444(3) Uani d . 1
C C13 0.15065(18) 0.10449(11) 0.37646(15) 0.0561(4) Uani d . 1
H H13 0.2368 0.1026 0.3505 0.067 Uiso calc R 1
C C14 0.0544(2) 0.05223(12) 0.31638(16) 0.0671(5) Uani d . 1
H H14 0.0769 0.0160 0.2502 0.081 Uiso calc R 1
C C15 -0.07066(19) 0.05416(11) 0.35403(17) 0.0664(5) Uani d . 1
H H15 -0.1336 0.0196 0.3127 0.080 Uiso calc R 1
C C16 -0.10736(16) 0.10754(10) 0.45481(16) 0.0551(4) Uani d . 1
C C17 -0.23701(18) 0.10888(14) 0.4998(2) 0.0739(6) Uani d . 1
H H17 -0.3012 0.0748 0.4595 0.089 Uiso calc R 1
C C18 -0.26922(19) 0.15838(16) 0.5993(2) 0.0842(7) Uani d . 1
H H18 -0.3551 0.1587 0.6261 0.101 Uiso calc R 1
C C19 -0.17432(19) 0.20892(14) 0.6620(2) 0.0787(6) Uani d . 1
H H19 -0.1970 0.2419 0.7317 0.094 Uiso calc R 1
C C20 -0.04846(16) 0.21082(11) 0.62276(17) 0.0594(4) Uani d . 1
H H20 0.0136 0.2452 0.6656 0.071 Uiso calc R 1
C C21 -0.01155(14) 0.16074(9) 0.51719(14) 0.0468(4) Uani d . 1
B B1 0.31636(19) 0.16560(13) 0.63406(19) 0.0569(5) Uani d . 1
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'
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
C11 O1 B1 125.10(13)
C1 N1 C12 119.32(12)
C1 N1 B1 121.74(13)
C12 N1 B1 118.78(12)
N1 C1 C2 122.95(14)
N1 C1 H1 118.5
C2 C1 H1 118.5
C11 C2 C1 117.63(14)
C11 C2 C3 120.02(13)
C1 C2 C3 122.34(14)
C4 C3 C8 117.75(15)
C4 C3 C2 124.20(14)
C8 C3 C2 118.03(15)
C5 C4 C3 121.04(17)
C5 C4 H4 119.5
C3 C4 H4 119.5
C4 C5 C6 120.9(2)
C4 C5 H5 119.5
C6 C5 H5 119.5
C7 C6 C5 119.87(19)
C7 C6 H6 120.1
C5 C6 H6 120.1
C6 C7 C8 120.89(18)
C6 C7 H7 119.6
C8 C7 H7 119.6
C7 C8 C9 121.52(17)
C7 C8 C3 119.52(17)
C9 C8 C3 118.96(16)
C10 C9 C8 122.76(16)
C10 C9 H9 118.6
C8 C9 H9 118.6
C9 C10 C11 119.61(17)
C9 C10 H10 120.2
C11 C10 H10 120.2
O1 C11 C2 121.94(14)
O1 C11 C10 117.46(15)
C2 C11 C10 120.59(16)
C13 C12 C21 121.83(14)
C13 C12 N1 119.46(13)
C21 C12 N1 118.63(13)
C12 C13 C14 119.76(16)
C12 C13 H13 120.1
C14 C13 H13 120.1
C15 C14 C13 120.48(17)
C15 C14 H14 119.8
C13 C14 H14 119.8
C14 C15 C16 121.07(16)
C14 C15 H15 119.5
C16 C15 H15 119.5
C15 C16 C21 119.42(15)
C15 C16 C17 122.50(17)
C21 C16 C17 118.05(17)
C18 C17 C16 121.61(19)
C18 C17 H17 119.2
C16 C17 H17 119.2
C17 C18 C19 120.14(18)
C17 C18 H18 119.9
C19 C18 H18 119.9
C20 C19 C18 121.0(2)
C20 C19 H19 119.5
C18 C19 H19 119.5
C19 C20 C21 120.46(18)
C19 C20 H20 119.8
C21 C20 H20 119.8
C12 C21 C20 123.80(14)
C12 C21 C16 117.41(14)
C20 C21 C16 118.75(14)
F1 B1 F2 109.98(17)
F1 B1 O1 109.44(15)
F2 B1 O1 109.25(15)
F1 B1 N1 110.18(14)
F2 B1 N1 107.95(14)
O1 B1 N1 110.02(14)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
F1 B1 1.354(2)
F2 B1 1.369(2)
O1 C11 1.327(2)
O1 B1 1.439(2)
N1 C1 1.2968(18)
N1 C12 1.4474(18)
N1 B1 1.564(2)
C1 C2 1.416(2)
C1 H1 0.9300
C2 C11 1.392(2)
C2 C3 1.440(2)
C3 C4 1.401(2)
C3 C8 1.420(2)
C4 C5 1.363(2)
C4 H4 0.9300
C5 C6 1.391(3)
C5 H5 0.9300
C6 C7 1.353(3)
C6 H6 0.9300
C7 C8 1.405(3)
C7 H7 0.9300
C8 C9 1.411(3)
C9 C10 1.345(3)
C9 H9 0.9300
C10 C11 1.407(2)
C10 H10 0.9300
C12 C13 1.357(2)
C12 C21 1.416(2)
C13 C14 1.404(2)
C13 H13 0.9300
C14 C15 1.350(3)
C14 H14 0.9300
C15 C16 1.406(3)
C15 H15 0.9300
C16 C21 1.419(2)
C16 C17 1.421(3)
C17 C18 1.348(3)
C17 H17 0.9300
C18 C19 1.391(3)
C18 H18 0.9300
C19 C20 1.363(2)
C19 H19 0.9300
C20 C21 1.417(2)
C20 H20 0.9300
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 21128006
