#------------------------------------------------------------------------------
#$Date: 2016-03-21 04:15:30 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178463 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/84/4028429.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_4028429
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         'C12 H8 B Cl F2 N2 O'
_chemical_formula_sum            'C12 H8 B Cl F2 N2 O'
_chemical_formula_weight         280.46
_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                 93.504(15)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.409(2)
_cell_length_b                   9.477(2)
_cell_length_c                   16.798(4)
_cell_measurement_temperature    293(2)
_cell_volume                     1177.3(5)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.980
_diffrn_measured_fraction_theta_max 0.980
_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  0.0400
_diffrn_reflns_av_sigmaI/netI    0.0283
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            11688
_diffrn_reflns_theta_full        27.51
_diffrn_reflns_theta_max         27.51
_diffrn_reflns_theta_min         2.47
_exptl_absorpt_coefficient_mu    0.341
_exptl_absorpt_correction_T_max  0.9350
_exptl_absorpt_correction_T_min  0.8901
_exptl_absorpt_correction_type   integration
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.582
_exptl_crystal_description       needle
_exptl_crystal_F_000             568
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.164
_refine_diff_density_min         -0.274
_refine_diff_density_rms         0.042
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     172
_refine_ls_number_reflns         2658
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.055
_refine_ls_R_factor_all          0.0771
_refine_ls_R_factor_gt           0.0495
_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)+(0.0579P)²+0.1939P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1131
_refine_ls_wR_factor_ref         0.1274
_reflns_number_gt                1907
_reflns_number_total             2658
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo400879g_si_001.cif
_cod_data_source_block           crystalclear
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               4028429
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
B1 B 0.1733(4) 0.2764(3) -0.02999(15) 0.0522(6) Uani 1 1 d .
O1 O 0.2318(3) 0.15361(16) -0.07166(9) 0.0753(6) Uani 1 1 d .
C1 C 0.2586(2) 0.0262(2) -0.04163(11) 0.0400(4) Uani 1 1 d .
C2 C 0.2378(3) -0.0001(2) 0.03641(11) 0.0433(5) Uani 1 1 d .
H2 H 0.2561 -0.0914 0.0555 0.052 Uiso 1 1 calc R
C3 C 0.1893(2) 0.1064(2) 0.08992(11) 0.0386(4) Uani 1 1 d .
N1 N 0.1596(2) 0.23946(17) 0.06187(10) 0.0434(4) Uani 1 1 d .
C4 C 0.1719(3) 0.0833(2) 0.17133(12) 0.0446(5) Uani 1 1 d .
H4 H 0.1901 -0.0058 0.1936 0.054 Uiso 1 1 calc R
C5 C 0.1174(4) 0.3420(2) 0.11275(14) 0.0576(6) Uani 1 1 d .
H5 H 0.0983 0.4319 0.0916 0.069 Uiso 1 1 calc R
N2 N 0.1009(3) 0.3267(2) 0.18963(11) 0.0562(5) Uani 1 1 d .
C6 C 0.3121(2) -0.0809(2) -0.09960(12) 0.0424(4) Uani 1 1 d .
C7 C 0.3458(3) -0.0396(2) -0.17702(13) 0.0515(5) Uani 1 1 d .
H7 H 0.3359 0.0549 -0.1915 0.062 Uiso 1 1 calc R
C8 C 0.3939(3) -0.1385(3) -0.23217(14) 0.0594(6) Uani 1 1 d .
H8 H 0.4144 -0.1104 -0.2839 0.071 Uiso 1 1 calc R
C9 C 0.4117(3) -0.2780(3) -0.21125(16) 0.0618(6) Uani 1 1 d .
H9 H 0.4451 -0.3439 -0.2487 0.074 Uiso 1 1 calc R
C10 C 0.3805(4) -0.3204(2) -0.13552(17) 0.0650(7) Uani 1 1 d .
H10 H 0.3930 -0.4150 -0.1215 0.078 Uiso 1 1 calc R
C11 C 0.3301(3) -0.2226(2) -0.07935(14) 0.0540(5) Uani 1 1 d .
H11 H 0.3083 -0.2521 -0.0280 0.065 Uiso 1 1 calc R
F1 F 0.2943(3) 0.38268(19) -0.03542(10) 0.0969(6) Uani 1 1 d .
F2 F 0.0062(2) 0.31730(18) -0.06011(9) 0.0849(5) Uani 1 1 d .
Cl1 Cl 0.10481(10) 0.17393(7) 0.31775(3) 0.0692(2) Uani 1 1 d .
C12 C 0.1275(3) 0.1953(2) 0.21682(12) 0.0447(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'
Cl Cl 0.1484 0.1585 '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
F1 B1 F2 110.6(2)
F1 B1 O1 110.4(2)
F2 B1 O1 110.1(2)
F1 B1 N1 108.09(19)
F2 B1 N1 108.15(19)
O1 B1 N1 109.46(17)
C1 O1 B1 126.68(17)
O1 C1 C2 121.06(18)
O1 C1 C6 114.65(17)
C2 C1 C6 124.30(18)
C1 C2 C3 122.25(18)
N1 C3 C4 117.50(17)
N1 C3 C2 118.97(17)
C4 C3 C2 123.53(18)
C5 N1 C3 119.31(17)
C5 N1 B1 119.26(17)
C3 N1 B1 121.43(16)
C12 C4 C3 117.83(18)
N2 C5 N1 125.8(2)
C5 N2 C12 114.77(19)
C11 C6 C7 118.64(19)
C11 C6 C1 121.88(19)
C7 C6 C1 119.48(19)
C8 C7 C6 120.2(2)
C9 C8 C7 120.5(2)
C10 C9 C8 120.1(2)
C9 C10 C11 120.2(2)
C10 C11 C6 120.3(2)
N2 C12 C4 124.80(19)
N2 C12 Cl1 115.09(16)
C4 C12 Cl1 120.11(17)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
B1 F1 1.355(3)
B1 F2 1.365(3)
B1 O1 1.438(3)
B1 N1 1.591(3)
O1 C1 1.319(2)
C1 C2 1.352(3)
C1 C6 1.477(3)
C2 C3 1.413(3)
C3 N1 1.359(2)
C3 C4 1.399(3)
N1 C5 1.344(3)
C4 C12 1.360(3)
C5 N2 1.313(3)
N2 C12 1.336(3)
C6 C11 1.390(3)
C6 C7 1.395(3)
C7 C8 1.380(3)
C8 C9 1.373(4)
C9 C10 1.367(4)
C10 C11 1.390(3)
Cl1 C12 1.726(2)
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
F1 B1 O1 C1 123.4(2)
F2 B1 O1 C1 -114.2(3)
N1 B1 O1 C1 4.5(4)
B1 O1 C1 C2 -2.4(4)
B1 O1 C1 C6 177.8(2)
O1 C1 C2 C3 -0.9(3)
C6 C1 C2 C3 178.95(18)
C1 C2 C3 N1 1.1(3)
C1 C2 C3 C4 -178.09(19)
C4 C3 N1 C5 0.7(3)
C2 C3 N1 C5 -178.5(2)
C4 C3 N1 B1 -179.17(19)
C2 C3 N1 B1 1.6(3)
F1 B1 N1 C5 55.8(3)
F2 B1 N1 C5 -64.0(3)
O1 B1 N1 C5 176.0(2)
F1 B1 N1 C3 -124.3(2)
F2 B1 N1 C3 115.9(2)
O1 B1 N1 C3 -4.0(3)
N1 C3 C4 C12 -0.3(3)
C2 C3 C4 C12 178.86(19)
C3 N1 C5 N2 -0.2(4)
B1 N1 C5 N2 179.8(2)
N1 C5 N2 C12 -0.8(4)
O1 C1 C6 C11 -174.3(2)
C2 C1 C6 C11 5.8(3)
O1 C1 C6 C7 5.8(3)
C2 C1 C6 C7 -174.10(19)
C11 C6 C7 C8 0.8(3)
C1 C6 C7 C8 -179.3(2)
C6 C7 C8 C9 -1.0(3)
C7 C8 C9 C10 0.5(4)
C8 C9 C10 C11 0.2(4)
C9 C10 C11 C6 -0.4(4)
C7 C6 C11 C10 -0.1(3)
C1 C6 C11 C10 179.9(2)
C5 N2 C12 C4 1.3(3)
C5 N2 C12 Cl1 -179.66(17)
C3 C4 C12 N2 -0.7(3)
C3 C4 C12 Cl1 -179.74(15)
