#------------------------------------------------------------------------------
#$Date: 2016-03-21 04:15:30 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178463 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/84/4028432.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_4028432
loop_
_publ_author_name
'Yasuhiro Kubota'
'Yousuke Ozaki'
'Kazumasa Funabiki'
'Masaki Matsui'
_publ_section_title
;
 Synthesis and Fluorescence Properties of Pyrimidine Mono- and Bisboron
 Complexes
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              7058
_journal_page_last               7067
_journal_paper_doi               10.1021/jo400879g
_journal_volume                  78
_journal_year                    2013
_chemical_formula_moiety         'C20 H14 B2 F4 N2 O2'
_chemical_formula_sum            'C20 H14 B2 F4 N2 O2'
_chemical_formula_weight         411.95
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           13
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yac'
_symmetry_space_group_name_H-M   'P 1 2/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                 94.824(13)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   7.175(7)
_cell_length_b                   7.220(7)
_cell_length_c                   17.702(17)
_cell_measurement_temperature    293(2)
_cell_volume                     913.8(15)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.975
_diffrn_measured_fraction_theta_max 0.975
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71075
_diffrn_reflns_av_R_equivalents  0.0369
_diffrn_reflns_av_sigmaI/netI    0.0286
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            8922
_diffrn_reflns_theta_full        27.48
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_min         2.82
_exptl_absorpt_coefficient_mu    0.123
_exptl_absorpt_correction_T_max  0.9758
_exptl_absorpt_correction_T_min  0.9758
_exptl_absorpt_correction_type   integration
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.497
_exptl_crystal_description       needle
_exptl_crystal_F_000             420
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.161
_refine_diff_density_min         -0.153
_refine_diff_density_rms         0.036
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     137
_refine_ls_number_reflns         2048
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.044
_refine_ls_R_factor_all          0.0774
_refine_ls_R_factor_gt           0.0513
_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)+(0.0603P)²+0.0872P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1155
_refine_ls_wR_factor_ref         0.1294
_reflns_number_gt                1441
_reflns_number_total             2048
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo400879g_si_004.cif
_cod_data_source_block           crystalclear
_cod_original_sg_symbol_H-M      'P 2/n'
_cod_database_code               4028432
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y, -z+1/2'
'-x, -y, -z'
'x-1/2, -y, 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
B1 B 0.9551(3) 0.6068(3) 0.16283(16) 0.0612(6) Uani 1 1 d .
O1 O 0.78628(17) 0.49876(16) 0.15073(8) 0.0620(4) Uani 1 1 d .
C1 C 0.7865(2) 0.3152(2) 0.14985(9) 0.0386(4) Uani 1 1 d .
C2 C 0.9376(2) 0.2151(2) 0.17786(9) 0.0381(4) Uani 1 1 d .
H2 H 0.9341 0.0868 0.1734 0.046 Uiso 1 1 calc R
C3 C 1.1000(2) 0.2995(2) 0.21355(8) 0.0340(3) Uani 1 1 d .
N1 N 1.10792(18) 0.48980(18) 0.21265(8) 0.0429(4) Uani 1 1 d .
C4 C 1.2500 0.2048(3) 0.2500 0.0354(5) Uani 1 2 d S
H4 H 1.2500 0.0759 0.2500 0.042 Uiso 1 2 calc SR
C5 C 1.2500 0.5747(3) 0.2500 0.0515(6) Uani 1 2 d S
H5 H 1.2500 0.7035 0.2500 0.062 Uiso 1 2 calc SR
C6 C 0.6088(2) 0.2312(2) 0.11818(8) 0.0391(4) Uani 1 1 d .
C7 C 0.4724(2) 0.3423(3) 0.07983(10) 0.0504(5) Uani 1 1 d .
H7 H 0.4923 0.4690 0.0756 0.060 Uiso 1 1 calc R
C8 C 0.3069(3) 0.2642(3) 0.04804(10) 0.0613(6) Uani 1 1 d .
H8 H 0.2171 0.3386 0.0221 0.074 Uiso 1 1 calc R
C9 C 0.2758(2) 0.0779(3) 0.05482(10) 0.0614(6) Uani 1 1 d .
H9 H 0.1650 0.0261 0.0334 0.074 Uiso 1 1 calc R
C10 C 0.4082(3) -0.0330(3) 0.09335(11) 0.0584(5) Uani 1 1 d .
H10 H 0.3864 -0.1593 0.0980 0.070 Uiso 1 1 calc R
C11 C 0.5737(2) 0.0432(2) 0.12508(10) 0.0470(4) Uani 1 1 d .
H11 H 0.6622 -0.0323 0.1512 0.056 Uiso 1 1 calc R
F1 F 1.0295(2) 0.6448(2) 0.09596(8) 0.0979(5) Uani 1 1 d .
F2 F 0.92477(18) 0.76506(16) 0.20168(9) 0.1000(6) 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
F2 B1 F1 111.10(19) .
F2 B1 O1 111.2(2) .
F1 B1 O1 111.37(19) .
F2 B1 N1 107.32(17) .
F1 B1 N1 106.58(18) .
O1 B1 N1 109.06(16) .
C1 O1 B1 122.76(15) .
O1 C1 C2 121.88(14) .
O1 C1 C6 114.37(13) .
C2 C1 C6 123.72(16) .
C1 C2 C3 122.31(16) .
N1 C3 C4 117.80(14) .
N1 C3 C2 117.27(13) .
C4 C3 C2 124.92(16) .
C5 N1 C3 119.31(15) .
C5 N1 B1 119.94(16) .
C3 N1 B1 120.63(13) .
C3 C4 C3 120.9(2) 2_755
N1 C5 N1 124.6(2) 2_755
C11 C6 C7 118.63(16) .
C11 C6 C1 121.66(14) .
C7 C6 C1 119.71(16) .
C8 C7 C6 120.27(19) .
C9 C8 C7 120.18(18) .
C8 C9 C10 120.18(18) .
C9 C10 C11 120.1(2) .
C10 C11 C6 120.59(17) .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
B1 F2 1.360(3) .
B1 F1 1.367(3) .
B1 O1 1.441(3) .
B1 N1 1.591(2) .
O1 C1 1.325(2) .
C1 C2 1.362(2) .
C1 C6 1.479(2) .
C2 C3 1.415(2) .
C3 N1 1.375(2) .
C3 C4 1.388(2) .
N1 C5 1.3185(18) .
C4 C3 1.388(2) 2_755
C5 N1 1.3184(18) 2_755
C6 C11 1.388(3) .
C6 C7 1.397(2) .
C7 C8 1.390(3) .
C8 C9 1.371(3) .
C9 C10 1.378(3) .
C10 C11 1.384(3) .
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_4
F2 B1 O1 C1 -146.05(17) .
F1 B1 O1 C1 89.4(2) .
N1 B1 O1 C1 -27.9(3) .
B1 O1 C1 C2 16.1(3) .
B1 O1 C1 C6 -165.54(18) .
O1 C1 C2 C3 3.7(3) .
C6 C1 C2 C3 -174.57(15) .
C1 C2 C3 N1 -6.2(2) .
C1 C2 C3 C4 173.02(13) .
C4 C3 N1 C5 -4.3(2) .
C2 C3 N1 C5 175.01(12) .
C4 C3 N1 B1 171.75(15) .
C2 C3 N1 B1 -9.0(2) .
F2 B1 N1 C5 -39.0(2) .
F1 B1 N1 C5 80.07(19) .
O1 B1 N1 C5 -159.59(15) .
F2 B1 N1 C3 145.00(17) .
F1 B1 N1 C3 -95.90(19) .
O1 B1 N1 C3 24.4(3) .
N1 C3 C4 C3 2.10(10) 2_755
C2 C3 C4 C3 -177.10(17) 2_755
C3 N1 C5 N1 2.21(10) 2_755
B1 N1 C5 N1 -173.82(18) 2_755
O1 C1 C6 C11 -168.58(15) .
C2 C1 C6 C11 9.8(2) .
O1 C1 C6 C7 11.8(2) .
C2 C1 C6 C7 -169.79(16) .
C11 C6 C7 C8 -1.3(2) .
C1 C6 C7 C8 178.26(15) .
C6 C7 C8 C9 0.7(3) .
C7 C8 C9 C10 0.1(3) .
C8 C9 C10 C11 -0.3(3) .
C9 C10 C11 C6 -0.4(3) .
C7 C6 C11 C10 1.2(3) .
C1 C6 C11 C10 -178.41(16) .
