#------------------------------------------------------------------------------
#$Date: 2016-02-20 02:53:41 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176768 $
#$URL: svn://www.crystallography.net/cod/cif/2/10/57/2105738.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_2105738
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 Cl2 O2'
_chemical_formula_sum            'C12 H8 B2 Cl2 O2'
_chemical_formula_weight         276.70
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2013
_cell_angle_alpha                90
_cell_angle_beta                 97.543(14)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   7.3645(10)
_cell_length_b                   3.8696(6)
_cell_length_c                   20.125(3)
_cell_measurement_reflns_used    1683
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      32.1156
_cell_measurement_theta_min      2.0375
_cell_volume                     568.55(15)
_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 1.000
_diffrn_measured_fraction_theta_max 0.954
_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  0.1092
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            8905
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         32.188
_diffrn_reflns_theta_min         2.042
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.555
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.421
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrysAlisPro (Agilent, 2011)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.616
_exptl_crystal_description       block
_exptl_crystal_F_000             280
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.13
_refine_diff_density_max         0.268
_refine_diff_density_min         -0.296
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.992
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     164
_refine_ls_number_reflns         1906
_refine_ls_number_restraints     12
_refine_ls_restrained_S_all      0.991
_refine_ls_R_factor_all          0.1405
_refine_ls_R_factor_gt           0.0644
_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)+(0.0509P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1342
_refine_ls_wR_factor_ref         0.1645
_reflns_number_gt                977
_reflns_number_total             1906
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            bi5017sup1.cif
_cod_data_source_block           III
_cod_database_code               2105738
_cod_database_fobs_code          2105738
#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+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -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
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl Cl1A 0.8344(4) 0.6810(8) 0.18884(12) 0.0320(5) Uani d 0.620(3) A 1
O O1A 1.3169(4) 0.6676(8) -0.05950(15) 0.0325(8) Uani d 0.620(3) A 1
H H1A 1.3260 0.5474 -0.0937 0.049 Uiso calc 0.620(3) A 1
B B1A 1.1643(9) 0.5740(15) -0.0330(4) 0.0190(10) Uani d 0.620(3) A 1
C C1A 1.1584(7) 0.6834(11) 0.0419(3) 0.0194(8) Uani d 0.620(3) A 1
C C2A 1.0027(10) 0.6193(15) 0.0747(3) 0.0195(11) Uani d 0.620(3) A 1
C C3A 1.0173(7) 0.7345(10) 0.1409(2) 0.0238(9) Uani d 0.620(3) A 1
C C4A 1.1703(7) 0.8983(11) 0.1751(3) 0.0280(11) Uani d 0.620(3) A 1
H H4A 1.1720 0.9695 0.2204 0.034 Uiso calc 0.620(3) A 1
C C5A 1.3210(16) 0.955(4) 0.1411(7) 0.034(3) Uani d 0.620(3) A 1
H H5A 1.4271 1.0674 0.1628 0.040 Uiso calc 0.620(3) A 1
C C6A 1.3146(5) 0.8457(10) 0.0753(2) 0.0243(9) Uani d 0.620(3) A 1
H H6A 1.4178 0.8815 0.0523 0.029 Uiso calc 0.620(3) A 1
Cl Cl1B 1.3689(7) 0.9588(19) 0.1505(3) 0.0359(10) Uani d 0.380(3) A 2
O O1B 1.3475(7) 0.8177(15) 0.0012(3) 0.0414(16) Uani d 0.380(3) A 2
H H1B 1.3897 0.9007 0.0387 0.062 Uiso calc 0.380(3) A 2
B B1B 1.1834(12) 0.653(2) 0.0064(7) 0.0215(16) Uani d 0.380(3) A 2
C C1B 1.0999(14) 0.477(2) -0.0604(5) 0.0193(15) Uani d 0.380(3) A 2
C C2B 1.0790(18) 0.662(2) 0.0692(4) 0.0202(18) Uani d 0.380(3) A 2
C C3B 1.1447(11) 0.807(2) 0.1331(5) 0.0308(17) Uani d 0.380(3) A 2
C C4B 1.0403(11) 0.8242(19) 0.1841(4) 0.0294(16) Uani d 0.380(3) A 2
H H4B 1.0873 0.9302 0.2253 0.035 Uiso calc 0.380(3) A 2
C C5B 0.867(2) 0.688(5) 0.1754(8) 0.032(4) Uani d 0.380(3) A 2
H H5B 0.7950 0.6922 0.2112 0.038 Uiso calc 0.380(3) A 2
C C6B 1.2021(10) 0.4566(18) -0.1147(4) 0.0270(16) Uani d 0.380(3) A 2
H H6B 1.3234 0.5458 -0.1093 0.032 Uiso calc 0.380(3) A 2
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'
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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
B1A O1A H1A . . 109.5
C6A C1A C2A . . 121.1(6)
C6A C1A B1A . . 117.1(6)
C2A C1A B1A . . 121.7(4)
C3A C2A C1A . . 115.1(6)
C3A C2A B1A . 3_765 127.9(7)
C1A C2A B1A . 3_765 117.0(5)
O1A B1A C1A . . 115.8(7)
O1A B1A C2A . 3_765 123.0(7)
C1A B1A C2A . 3_765 121.2(4)
C4A C3A C2A . . 125.0(6)
C4A C3A Cl1A . . 114.0(4)
C2A C3A Cl1A . . 121.0(5)
C3A C4A C5A . . 118.1(7)
C3A C4A H4A . . 120.9
C5A C4A H4A . . 120.9
C6A C5A C4A . . 119.5(9)
C6A C5A H5A . . 120.3
C4A C5A H5A . . 120.3
C5A C6A C1A . . 121.2(7)
C5A C6A H6A . . 119.4
C1A C6A H6A . . 119.4
C4B C5B C6B . 3_765 119.9(10)
C4B C5B H5B . . 120.1
C6B C5B H5B 3_765 . 120.1
C4B C3B C2B . . 122.6(9)
C4B C3B Cl1B . . 116.5(8)
C2B C3B Cl1B . . 120.9(8)
C6B C1B C2B . 3_765 117.8(10)
C6B C1B B1B . . 120.2(11)
C2B C1B B1B 3_765 . 122.0(7)
B1B O1B H1B . . 109.5
C1B C2B C3B 3_765 . 117.5(9)
C1B C2B B1B 3_765 . 116.1(8)
C3B C2B B1B . . 126.3(11)
C3B C4B C5B . . 119.6(10)
C3B C4B H4B . . 120.2
C5B C4B H4B . . 120.2
O1B B1B C1B . . 112.8(11)
O1B B1B C2B . . 125.3(12)
C1B B1B C2B . . 121.7(7)
C5B C6B C1B 3_765 . 122.5(10)
C5B C6B H6B 3_765 . 118.8
C1B C6B H6B . . 118.8
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
Cl1A C3A . 1.770(5)
O1A B1A . 1.355(6)
O1A H1A . 0.8400
C1A C6A . 1.402(6)
C1A C2A . 1.418(7)
C1A B1A . 1.571(8)
C2A C3A . 1.395(8)
C2A B1A 3_765 1.583(9)
B1A C2A 3_765 1.583(9)
C3A C4A . 1.394(7)
C4A C5A . 1.396(15)
C4A H4A . 0.9500
C5A C6A . 1.385(15)
C5A H5A . 0.9500
C6A H6A . 0.9500
C5B C4B . 1.370(19)
C5B C6B 3_765 1.379(19)
C5B H5B . 0.9500
Cl1B C3B . 1.744(10)
C3B C4B . 1.361(12)
C3B C2B . 1.429(15)
C1B C6B . 1.409(9)
C1B C2B 3_765 1.412(11)
C1B B1B . 1.560(12)
O1B B1B . 1.382(10)
O1B H1B . 0.8400
C2B C1B 3_765 1.412(11)
C2B B1B . 1.564(14)
C4B H4B . 0.9500
C6B C5B 3_765 1.379(19)
C6B H6B . 0.9500
