#------------------------------------------------------------------------------
#$Date: 2016-03-21 02:55:05 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178411 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/32/4023274.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_4023274
loop_
_publ_author_name
'Ying Zhou'
'Yi Xiao'
'Dan Li'
'Meiyan Fu'
'Xuhong Qian'
_publ_section_title
;
 Novel Fluorescent Fluorine-Boron Complexes: Synthesis, Crystal
 Structure, Photoluminescence, and Electrochemistry Properties
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              1571
_journal_page_last               1574
_journal_paper_doi               10.1021/jo702265x
_journal_volume                  73
_journal_year                    2008
_chemical_formula_sum            'C18 H11 B F2 N2 O'
_chemical_formula_weight         320.10
_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                 101.136(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.6750(10)
_cell_length_b                   11.4882(13)
_cell_length_c                   14.4342(18)
_cell_measurement_reflns_used    1361
_cell_measurement_temperature    273(2)
_cell_measurement_theta_max      24.27
_cell_measurement_theta_min      2.88
_cell_volume                     1411.4(3)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      273(2)
_diffrn_measured_fraction_theta_full 0.985
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega 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  0.0346
_diffrn_reflns_av_sigmaI/netI    0.0504
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            7810
_diffrn_reflns_theta_full        27.40
_diffrn_reflns_theta_max         27.40
_diffrn_reflns_theta_min         2.39
_exptl_absorpt_coefficient_mu    0.112
_exptl_absorpt_correction_T_max  0.9747
_exptl_absorpt_correction_T_min  0.9555
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            YELLOW
_exptl_crystal_density_diffrn    1.506
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    .
_exptl_crystal_description       column
_exptl_crystal_F_000             656
_exptl_crystal_size_max          0.41
_exptl_crystal_size_mid          0.34
_exptl_crystal_size_min          0.23
_refine_diff_density_max         0.151
_refine_diff_density_min         -0.183
_refine_diff_density_rms         0.039
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.999
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     217
_refine_ls_number_reflns         3158
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.999
_refine_ls_R_factor_all          0.0937
_refine_ls_R_factor_gt           0.0446
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0582P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1025
_refine_ls_wR_factor_ref         0.1229
_reflns_number_gt                1821
_reflns_number_total             3158
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo702265x-File004.cif
_cod_data_source_block           2
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 
;
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               4023274
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 0.17429(13) 0.18561(11) 0.20968(8) 0.0676(4) Uani 1 1 d . . .
F2 F 0.28752(13) 0.36424(11) 0.21585(8) 0.0718(4) Uani 1 1 d . . .
N1 N 0.37806(15) 0.21714(13) 0.12314(10) 0.0421(4) Uani 1 1 d . . .
N2 N 0.10912(15) 0.30858(12) 0.07144(10) 0.0380(4) Uani 1 1 d . . .
O1 O 0.53572(16) 0.16198(14) 0.26540(10) 0.0674(5) Uani 1 1 d . . .
B1 B 0.2411(2) 0.2678(2) 0.15982(15) 0.0448(6) Uani 1 1 d . . .
C1 C -0.03156(19) 0.35445(15) 0.08939(13) 0.0401(5) Uani 1 1 d . . .
C2 C -0.0556(2) 0.37177(18) 0.18153(14) 0.0532(5) Uani 1 1 d . . .
H2A H 0.0231 0.3521 0.2325 0.064 Uiso 1 1 calc R . .
C3 C -0.1942(2) 0.4175(2) 0.19720(15) 0.0638(6) Uani 1 1 d . . .
H3A H -0.2079 0.4286 0.2589 0.077 Uiso 1 1 calc R . .
C4 C -0.3150(2) 0.4475(2) 0.12272(17) 0.0658(6) Uani 1 1 d . . .
H4A H -0.4083 0.4785 0.1345 0.079 Uiso 1 1 calc R . .
C5 C -0.2950(2) 0.43122(19) 0.03293(16) 0.0578(6) Uani 1 1 d . . .
H5A H -0.3761 0.4503 -0.0169 0.069 Uiso 1 1 calc R . .
C6 C -0.15287(19) 0.38562(16) 0.01355(13) 0.0421(5) Uani 1 1 d . . .
C7 C -0.1290(2) 0.37196(17) -0.07911(14) 0.0493(5) Uani 1 1 d . . .
H7A H -0.2086 0.3911 -0.1298 0.059 Uiso 1 1 calc R . .
C8 C 0.0091(2) 0.33114(16) -0.09472(13) 0.0465(5) Uani 1 1 d . . .
H8A H 0.0254 0.3247 -0.1563 0.056 Uiso 1 1 calc R . .
C9 C 0.13006(19) 0.29780(15) -0.01860(12) 0.0387(4) Uani 1 1 d . . .
C10 C 0.27321(19) 0.25125(16) -0.03907(13) 0.0435(5) Uani 1 1 d . . .
H10A H 0.2862 0.2481 -0.1015 0.052 Uiso 1 1 calc R . .
C11 C 0.38908(19) 0.21200(16) 0.02939(12) 0.0403(4) Uani 1 1 d . . .
C12 C 0.5396(2) 0.15645(15) 0.02302(13) 0.0412(5) Uani 1 1 d . . .
C13 C 0.6061(2) 0.12827(18) -0.05340(15) 0.0529(5) Uani 1 1 d . . .
H13A H 0.5560 0.1453 -0.1148 0.064 Uiso 1 1 calc R . .
C14 C 0.7508(2) 0.0735(2) -0.03449(15) 0.0628(6) Uani 1 1 d . . .
H14A H 0.7985 0.0527 -0.0845 0.075 Uiso 1 1 calc R . .
C15 C 0.8265(2) 0.0487(2) 0.05670(16) 0.0640(6) Uani 1 1 d . . .
H15A H 0.9240 0.0121 0.0667 0.077 Uiso 1 1 calc R . .
C16 C 0.7602(2) 0.07714(19) 0.13292(15) 0.0560(6) Uani 1 1 d . . .
H16A H 0.8110 0.0610 0.1944 0.067 Uiso 1 1 calc R . .
C17 C 0.6143(2) 0.13087(16) 0.11412(13) 0.0441(5) Uani 1 1 d . . .
C18 C 0.5126(2) 0.16903(17) 0.17979(14) 0.0469(5) Uani 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'
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
C11 N1 C18 110.38(15) . . ?
C11 N1 B1 124.82(14) . . ?
C18 N1 B1 124.80(15) . . ?
C9 N2 C1 119.77(14) . . ?
C9 N2 B1 121.85(15) . . ?
C1 N2 B1 118.37(15) . . ?
F1 B1 F2 110.28(17) . . ?
F1 B1 N1 110.93(17) . . ?
F2 B1 N1 110.76(16) . . ?
F1 B1 N2 107.79(15) . . ?
F2 B1 N2 108.19(16) . . ?
N1 B1 N2 108.78(15) . . ?
N2 C1 C2 121.67(15) . . ?
N2 C1 C6 119.92(17) . . ?
C2 C1 C6 118.41(17) . . ?
C3 C2 C1 120.52(18) . . ?
C2 C3 C4 121.4(2) . . ?
C5 C4 C3 119.3(2) . . ?
C4 C5 C6 121.18(18) . . ?
C7 C6 C1 119.14(16) . . ?
C7 C6 C5 121.64(16) . . ?
C1 C6 C5 119.22(19) . . ?
C8 C7 C6 119.96(16) . . ?
C7 C8 C9 120.94(19) . . ?
N2 C9 C8 120.23(16) . . ?
N2 C9 C10 120.97(14) . . ?
C8 C9 C10 118.80(17) . . ?
C11 C10 C9 121.86(17) . . ?
C10 C11 N1 121.63(17) . . ?
C10 C11 C12 130.23(17) . . ?
N1 C11 C12 108.12(14) . . ?
C13 C12 C17 121.33(17) . . ?
C13 C12 C11 131.70(16) . . ?
C17 C12 C11 106.96(16) . . ?
C12 C13 C14 116.94(18) . . ?
C15 C14 C13 121.8(2) . . ?
C16 C15 C14 121.16(19) . . ?
C15 C16 C17 117.13(18) . . ?
C12 C17 C16 121.59(18) . . ?
C12 C17 C18 108.57(15) . . ?
C16 C17 C18 129.84(17) . . ?
O1 C18 N1 125.03(18) . . ?
O1 C18 C17 128.99(17) . . ?
N1 C18 C17 105.97(15) . . ?
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 B1 1.381(3) . ?
F2 B1 1.384(3) . ?
N1 C11 1.376(2) . ?
N1 C18 1.403(2) . ?
N1 B1 1.508(3) . ?
N2 C9 1.352(2) . ?
N2 C1 1.399(2) . ?
N2 B1 1.611(2) . ?
O1 C18 1.216(2) . ?
C1 C2 1.400(3) . ?
C1 C6 1.410(2) . ?
C2 C3 1.371(3) . ?
C3 C4 1.392(3) . ?
C4 C5 1.353(3) . ?
C5 C6 1.416(3) . ?
C6 C7 1.401(3) . ?
C7 C8 1.346(3) . ?
C8 C9 1.418(2) . ?
C9 C10 1.434(2) . ?
C10 C11 1.344(2) . ?
C11 C12 1.472(2) . ?
C12 C13 1.378(3) . ?
C12 C17 1.381(3) . ?
C13 C14 1.384(3) . ?
C14 C15 1.382(3) . ?
C15 C16 1.376(3) . ?
C16 C17 1.387(2) . ?
C17 C18 1.481(3) . ?
