#------------------------------------------------------------------------------
#$Date: 2016-03-21 02:55:05 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178411 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/32/4023273.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_4023273
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            'C14 H9 B F2 N2 O'
_chemical_formula_weight         270.04
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 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                 109.830(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   11.4034(3)
_cell_length_b                   8.9648(2)
_cell_length_c                   12.4160(3)
_cell_measurement_reflns_used    1895
_cell_measurement_temperature    273(2)
_cell_measurement_theta_max      26.92
_cell_measurement_theta_min      2.96
_cell_volume                     1194.01(5)
_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 0.921
_diffrn_measured_fraction_theta_max 0.921
_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  0.0234
_diffrn_reflns_av_sigmaI/netI    0.0255
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            4618
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         2.10
_exptl_absorpt_coefficient_mu    0.117
_exptl_absorpt_correction_T_max  0.9714
_exptl_absorpt_correction_T_min  0.9494
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.502
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    .
_exptl_crystal_F_000             552
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.34
_exptl_crystal_size_min          0.25
_refine_diff_density_max         0.165
_refine_diff_density_min         -0.130
_refine_diff_density_rms         0.033
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.995
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     181
_refine_ls_number_reflns         1939
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.995
_refine_ls_R_factor_all          0.0457
_refine_ls_R_factor_gt           0.0349
_refine_ls_shift/su_max          0.011
_refine_ls_shift/su_mean         0.002
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0612P)²+0.1969P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0976
_refine_ls_wR_factor_ref         0.1049
_reflns_number_gt                1547
_reflns_number_total             1939
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo702265x-File003.cif
_cod_data_source_block           1
_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/n'
_cod_database_code               4023273
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -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 0.17798(12) 0.07219(15) -0.00397(11) 0.0405(3) Uani 1 1 d . . .
O1 O 0.35855(12) -0.06956(17) 0.05014(12) 0.0733(5) Uani 1 1 d . . .
B1 B 0.19996(17) 0.1697(2) 0.10087(15) 0.0442(5) Uani 1 1 d . . .
F1 F 0.29087(9) 0.27604(13) 0.10895(10) 0.0663(4) Uani 1 1 d . . .
C1 C 0.07018(17) 0.3349(2) 0.17895(14) 0.0480(4) Uani 1 1 d . . .
H1A H 0.1370 0.3272 0.2472 0.058 Uiso 1 1 calc R . .
N2 N 0.07442(12) 0.25844(14) 0.08618(10) 0.0385(3) Uani 1 1 d . . .
C2 C -0.02843(18) 0.4224(2) 0.17586(15) 0.0522(5) Uani 1 1 d . . .
H2A H -0.0291 0.4733 0.2409 0.063 Uiso 1 1 calc R . .
F2 F 0.23075(10) 0.08937(13) 0.20110(8) 0.0628(3) Uani 1 1 d . . .
C3 C -0.12734(17) 0.4343(2) 0.07470(15) 0.0522(5) Uani 1 1 d . . .
H3A H -0.1954 0.4940 0.0706 0.063 Uiso 1 1 calc R . .
C4 C -0.12450(16) 0.3573(2) -0.02015(14) 0.0469(4) Uani 1 1 d . . .
H4A H -0.1909 0.3650 -0.0887 0.056 Uiso 1 1 calc R . .
C5 C -0.02276(14) 0.26798(18) -0.01406(13) 0.0384(4) Uani 1 1 d . . .
C6 C -0.01709(14) 0.18434(19) -0.11114(13) 0.0407(4) Uani 1 1 d . . .
H6A H -0.0810 0.1952 -0.1811 0.049 Uiso 1 1 calc R . .
C7 C 0.07694(14) 0.09176(18) -0.10396(13) 0.0376(4) Uani 1 1 d . . .
C8 C 0.09632(15) -0.00401(18) -0.19250(13) 0.0406(4) Uani 1 1 d . . .
C9 C 0.02431(17) -0.0281(2) -0.30573(14) 0.0491(4) Uani 1 1 d . . .
H9A H -0.0521 0.0195 -0.3385 0.059 Uiso 1 1 calc R . .
C10 C 0.0700(2) -0.1252(2) -0.36828(16) 0.0586(5) Uani 1 1 d . . .
H10A H 0.0232 -0.1443 -0.4444 0.070 Uiso 1 1 calc R . .
C11 C 0.1844(2) -0.1948(2) -0.31958(17) 0.0637(6) Uani 1 1 d . . .
H11A H 0.2136 -0.2584 -0.3640 0.076 Uiso 1 1 calc R . .
C12 C 0.25562(19) -0.1716(2) -0.20679(17) 0.0603(5) Uani 1 1 d . . .
H12A H 0.3321 -0.2190 -0.1742 0.072 Uiso 1 1 calc R . .
C13 C 0.20958(16) -0.07541(19) -0.14329(14) 0.0453(4) Uani 1 1 d . . .
C14 C 0.26226(16) -0.0294(2) -0.02196(15) 0.0484(4) 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
C7 N1 C14 110.29(14) . . ?
C7 N1 B1 122.68(13) . . ?
C14 N1 B1 126.23(14) . . ?
F2 B1 F1 109.82(14) . . ?
F2 B1 N1 113.07(16) . . ?
F1 B1 N1 111.12(14) . . ?
F2 B1 N2 107.96(13) . . ?
F1 B1 N2 106.59(15) . . ?
N1 B1 N2 108.00(12) . . ?
N2 C1 C2 122.33(16) . . ?
C1 N2 C5 119.55(15) . . ?
C1 N2 B1 116.42(13) . . ?
C5 N2 B1 123.91(13) . . ?
C1 C2 C3 118.91(16) . . ?
C4 C3 C2 119.45(17) . . ?
C3 C4 C5 120.28(16) . . ?
N2 C5 C4 119.47(14) . . ?
N2 C5 C6 118.65(14) . . ?
C4 C5 C6 121.88(14) . . ?
C7 C6 C5 122.09(15) . . ?
C6 C7 N1 122.84(14) . . ?
C6 C7 C8 129.39(15) . . ?
N1 C7 C8 107.77(14) . . ?
C9 C8 C13 121.32(16) . . ?
C9 C8 C7 131.54(15) . . ?
C13 C8 C7 107.13(14) . . ?
C10 C9 C8 117.55(17) . . ?
C9 C10 C11 121.15(18) . . ?
C12 C11 C10 121.27(17) . . ?
C11 C12 C13 117.79(18) . . ?
C8 C13 C12 120.89(17) . . ?
C8 C13 C14 108.46(15) . . ?
C12 C13 C14 130.65(17) . . ?
O1 C14 N1 125.15(17) . . ?
O1 C14 C13 128.52(17) . . ?
N1 C14 C13 106.33(14) . . ?
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 C7 1.389(2) . ?
N1 C14 1.396(2) . ?
N1 B1 1.516(2) . ?
O1 C14 1.212(2) . ?
B1 F2 1.376(2) . ?
B1 F1 1.387(2) . ?
B1 N2 1.593(2) . ?
C1 N2 1.355(2) . ?
C1 C2 1.361(2) . ?
N2 C5 1.360(2) . ?
C2 C3 1.378(3) . ?
C3 C4 1.375(2) . ?
C4 C5 1.391(2) . ?
C5 C6 1.440(2) . ?
C6 C7 1.335(2) . ?
C7 C8 1.469(2) . ?
C8 C9 1.383(2) . ?
C8 C13 1.384(2) . ?
C9 C10 1.381(3) . ?
C10 C11 1.387(3) . ?
C11 C12 1.376(3) . ?
C12 C13 1.387(2) . ?
C13 C14 1.479(3) . ?
