#------------------------------------------------------------------------------
#$Date: 2016-02-20 02:53:41 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176768 $
#$URL: svn://www.crystallography.net/cod/cif/2/10/57/2105737.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_2105737
loop_
_publ_author_name
'Durka, Krzysztof'
'Luliński, Sergiusz'
'Jarzembska, Katarzyna N.'
'Smetek, Jaromir'
'Serwatowski, Janusz'
'Woźniak, Krzysztof'
_publ_section_title
;
 Competition between hydrogen and halogen bonding in the structures of
 5,10-dihydroxy-5,10-dihydroboranthrenes
;
_journal_coeditor_code           BI5017
_journal_issue                   1
_journal_name_full               'Acta Crystallographica Section B'
_journal_page_first              157
_journal_page_last               171
_journal_paper_doi               10.1107/S2052520613034987
_journal_volume                  70
_journal_year                    2014
_chemical_formula_moiety         'C12 H8 B2 F2 O2'
_chemical_formula_sum            'C12 H8 B2 F2 O2'
_chemical_formula_weight         243.80
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2013
_cell_angle_alpha                90
_cell_angle_beta                 117.51(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   17.909(6)
_cell_length_b                   3.77900(10)
_cell_length_c                   17.355(3)
_cell_measurement_reflns_used    15096
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      34.4890
_cell_measurement_theta_min      2.2226
_cell_volume                     1041.7(5)
_computing_cell_refinement       CrysAlisPro
_computing_data_collection       'CrysAlisPro (Agilent, 2011)'
_computing_data_reduction        CrysAlisPro
_computing_molecular_graphics    'SHELXTL (Bruker, 2011)'
_computing_publication_material  SHELXL-2013
_computing_structure_refinement  SHELXL-2013
_computing_structure_solution    'SHELXS-2013 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.973
_diffrn_measurement_device_type  'KUMA KM4 CCD'
_diffrn_measurement_method       'ω 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  0.0410
_diffrn_reflns_limit_h_max       28
_diffrn_reflns_limit_h_min       -28
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            45182
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         34.565
_diffrn_reflns_theta_min         2.348
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.124
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.995
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrysAlisPro (Agilent, 2011)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.555
_exptl_crystal_description       block
_exptl_crystal_F_000             496
_exptl_crystal_size_max          0.11
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.07
_refine_diff_density_max         0.457
_refine_diff_density_min         -0.259
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     163
_refine_ls_number_reflns         4294
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.028
_refine_ls_R_factor_all          0.0640
_refine_ls_R_factor_gt           0.0426
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0642P)²+0.3315P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1110
_refine_ls_wR_factor_ref         0.1241
_reflns_number_gt                3245
_reflns_number_total             4294
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            bi5017sup1.cif
_cod_data_source_block           II
_cod_database_code               2105737
#BEGIN Tags that were not found in dictionaries:
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
#END Tags that were not found in dictionaries
loop_
_space_group_symop_operation_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_occupancy
C C5 0.28586(6) 0.2283(3) 0.31060(7) 0.01845(19) Uani d 1
H H5 0.2300 0.1394 0.2810 0.022 Uiso calc 1
C C1 0.41071(6) 0.3603(3) 0.44649(6) 0.01310(17) Uani d 1
C C2 0.45225(6) 0.4940(3) 0.40022(6) 0.01331(17) Uani d 1
C C3 0.40672(6) 0.4843(3) 0.31000(6) 0.01531(18) Uani d 1
C C4 0.32562(6) 0.3575(3) 0.26389(7) 0.01831(19) Uani d 1
H H4 0.2978 0.3586 0.2022 0.022 Uiso calc 1
C C6 0.32842(6) 0.2300(3) 0.40087(6) 0.01593(18) Uani d 1
H H6 0.3010 0.1407 0.4324 0.019 Uiso calc 1
C C7 0.08711(5) 0.8320(3) 0.53297(6) 0.01212(16) Uani d 1
C C8 0.04521(6) 0.9370(3) 0.44467(6) 0.01214(16) Uani d 1
C C9 0.08874(6) 0.8749(3) 0.39707(6) 0.01450(17) Uani d 1
C C10 0.16693(6) 0.7200(3) 0.42871(7) 0.01686(19) Uani d 1
H H10 0.1926 0.6820 0.3922 0.020 Uiso calc 1
C C11 0.20712(6) 0.6210(3) 0.51571(7) 0.01738(19) Uani d 1
H H11 0.2614 0.5156 0.5400 0.021 Uiso calc 1
C C12 0.16717(6) 0.6777(3) 0.56694(6) 0.01534(18) Uani d 1
H H12 0.1948 0.6101 0.6264 0.018 Uiso calc 1
B B1 0.54389(6) 0.6446(3) 0.45154(7) 0.01407(19) Uani d 1
B B2 0.04423(6) 0.8881(3) 0.59308(7) 0.01328(18) Uani d 1
O O1 0.58821(5) 0.7887(2) 0.41325(5) 0.02121(17) Uani d 1
H H1A 0.5583 0.7889 0.3591 0.032 Uiso calc 1
O O2 0.08905(5) 0.7770(3) 0.67653(5) 0.02172(18) Uani d 1
H H2 0.0614 0.8164 0.7037 0.033 Uiso calc 1
F F1 0.44392(4) 0.61138(19) 0.26178(4) 0.02121(15) Uani d 1
F F2 0.05177(4) 0.9789(2) 0.31154(4) 0.02156(15) 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'
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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
C6 C5 C4 . . 119.55(9)
C6 C5 H5 . . 120.2
C4 C5 H5 . . 120.2
C6 C1 C2 . . 119.73(9)
C6 C1 B1 . 3_666 119.66(9)
C2 C1 B1 . 3_666 120.62(9)
C3 C2 C1 . . 116.12(9)
C3 C2 B1 . . 124.31(9)
C1 C2 B1 . . 119.57(9)
F1 C3 C4 . . 116.37(9)
F1 C3 C2 . . 118.60(9)
C4 C3 C2 . . 125.02(10)
C3 C4 C5 . . 117.95(10)
C3 C4 H4 . . 121.0
C5 C4 H4 . . 121.0
C5 C6 C1 . . 121.64(10)
C5 C6 H6 . . 119.2
C1 C6 H6 . . 119.2
C12 C7 C8 . . 119.99(9)
C12 C7 B2 . . 119.77(9)
C8 C7 B2 . . 120.25(8)
C9 C8 C7 . . 115.62(9)
C9 C8 B2 . 3_576 124.50(9)
C7 C8 B2 . 3_576 119.88(9)
F2 C9 C10 . . 116.52(9)
F2 C9 C8 . . 118.03(9)
C10 C9 C8 . . 125.44(9)
C9 C10 C11 . . 117.95(9)
C9 C10 H10 . . 121.0
C11 C10 H10 . . 121.0
C10 C11 C12 . . 119.42(9)
C10 C11 H11 . . 120.3
C12 C11 H11 . . 120.3
C11 C12 C7 . . 121.57(9)
C11 C12 H12 . . 119.2
C7 C12 H12 . . 119.2
O1 B1 C2 . . 124.11(9)
O1 B1 C1 . 3_666 116.08(9)
C2 B1 C1 . 3_666 119.81(9)
O2 B2 C8 . 3_576 124.19(9)
O2 B2 C7 . . 115.94(9)
C8 B2 C7 3_576 . 119.87(9)
B1 O1 H1A . . 109.5
B2 O2 H2 . . 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
C5 C6 . 1.3901(15)
C5 C4 . 1.3915(15)
C5 H5 . 0.9500
C1 C6 . 1.4011(15)
C1 C2 . 1.4162(13)
C1 B1 3_666 1.5696(16)
C2 C3 . 1.3922(15)
C2 B1 . 1.5685(16)
C3 F1 . 1.3748(12)
C3 C4 . 1.3805(16)
C4 H4 . 0.9500
C6 H6 . 0.9500
C7 C12 . 1.4008(14)
C7 C8 . 1.4165(14)
C7 B2 . 1.5696(14)
C8 C9 . 1.3930(13)
C8 B2 3_576 1.5690(16)
C9 F2 . 1.3741(12)
C9 C10 . 1.3763(15)
C10 C11 . 1.3906(16)
C10 H10 . 0.9500
C11 C12 . 1.3914(14)
C11 H11 . 0.9500
C12 H12 . 0.9500
B1 O1 . 1.3620(13)
B1 C1 3_666 1.5696(16)
B2 O2 . 1.3581(14)
B2 C8 3_576 1.5691(16)
O1 H1A . 0.8400
O2 H2 . 0.8400
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_site_symmetry_1
_geom_torsion_site_symmetry_4
_geom_torsion
C6 C1 C2 C3 . . -0.24(14)
B1 C1 C2 C3 3_666 . 179.56(9)
C6 C1 C2 B1 . . 179.12(9)
B1 C1 C2 B1 3_666 . -1.08(16)
C1 C2 C3 F1 . . 179.88(9)
B1 C2 C3 F1 . . 0.56(15)
C1 C2 C3 C4 . . 0.34(15)
B1 C2 C3 C4 . . -178.99(10)
F1 C3 C4 C5 . . -179.71(9)
C2 C3 C4 C5 . . -0.16(17)
C6 C5 C4 C3 . . -0.12(16)
C4 C5 C6 C1 . . 0.21(16)
C2 C1 C6 C5 . . -0.02(15)
B1 C1 C6 C5 3_666 . -179.83(10)
C12 C7 C8 C9 . . 0.16(14)
B2 C7 C8 C9 . . -179.92(9)
C12 C7 C8 B2 . 3_576 -179.64(9)
B2 C7 C8 B2 . 3_576 0.29(16)
C7 C8 C9 F2 . . -178.59(9)
B2 C8 C9 F2 3_576 . 1.19(15)
C7 C8 C9 C10 . . 0.65(15)
B2 C8 C9 C10 3_576 . -179.56(10)
F2 C9 C10 C11 . . 178.19(9)
C8 C9 C10 C11 . . -1.06(16)
C9 C10 C11 C12 . . 0.64(16)
C10 C11 C12 C7 . . 0.11(16)
C8 C7 C12 C11 . . -0.52(15)
B2 C7 C12 C11 . . 179.55(10)
C3 C2 B1 O1 . . 1.36(16)
C1 C2 B1 O1 . . -177.95(10)
C3 C2 B1 C1 . 3_666 -179.63(9)
C1 C2 B1 C1 . 3_666 1.07(15)
C12 C7 B2 O2 . . -0.47(15)
C8 C7 B2 O2 . . 179.60(9)
C12 C7 B2 C8 . 3_576 179.64(9)
C8 C7 B2 C8 . 3_576 -0.29(16)
