#------------------------------------------------------------------------------
#$Date: 2016-03-24 14:34:44 +0200 (Thu, 24 Mar 2016) $
#$Revision: 179668 $
#$URL: svn://www.crystallography.net/cod/cif/4/51/21/4512185.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_4512185
loop_
_publ_author_name
'Madura, Izabela D.'
'Czerwińska, Karolina'
'Sołdańska, Dominika'
_publ_section_title
;
 Hydrogen-Bonded Dimeric Synthon of Fluoro-Substituted Phenylboronic Acids
 versus Supramolecular Organization in Crystals
;
_journal_issue                   11
_journal_name_full               'Crystal Growth & Design'
_journal_page_first              5912
_journal_paper_doi               10.1021/cg501132d
_journal_volume                  14
_journal_year                    2014
_chemical_formula_moiety         'C6 H5 B F2 O2'
_chemical_formula_sum            'C6 H5 B F2 O2'
_chemical_formula_weight         157.91
_chemical_name_systematic        '2,5-difluorophenylboronic acid'
_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   mixed
_atom_sites_solution_primary     direct
_audit_creation_method
;
Olex2 1.2-beta
(compiled 2014.03.12 svn.r2899 for OlexSys, GUI svn.r4796)
;
_cell_angle_alpha                90
_cell_angle_beta                 90.0696(14)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   4.15299(7)
_cell_length_b                   5.11382(9)
_cell_length_c                   30.7324(5)
_cell_measurement_reflns_used    7083
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      66.9520
_cell_measurement_theta_min      5.7530
_cell_volume                     652.683(19)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      100.0
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.3347
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.983
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini ultra'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0274561000
_diffrn_orient_matrix_UB_12      -0.0402432000
_diffrn_orient_matrix_UB_13      0.0495443000
_diffrn_orient_matrix_UB_21      -0.3576042000
_diffrn_orient_matrix_UB_22      -0.0732013000
_diffrn_orient_matrix_UB_23      -0.0053257000
_diffrn_orient_matrix_UB_31      0.0943365000
_diffrn_orient_matrix_UB_32      -0.2894786000
_diffrn_orient_matrix_UB_33      -0.0055298000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0251
_diffrn_reflns_av_unetI/netI     0.0101
_diffrn_reflns_Laue_measured_fraction_full 0.983
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       36
_diffrn_reflns_limit_l_min       -36
_diffrn_reflns_number            9624
_diffrn_reflns_point_group_measured_fraction_full 0.983
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         67.125
_diffrn_reflns_theta_min         5.759
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'Enhance Ultra (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.341
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.53618
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.607
_exptl_crystal_description       plate
_exptl_crystal_F_000             320
_exptl_crystal_size_max          0.07
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.354
_refine_diff_density_min         -0.217
_refine_diff_density_rms         0.043
_refine_ls_extinction_coef       0.0093(14)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.108
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     107
_refine_ls_number_reflns         1143
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.108
_refine_ls_R_factor_all          0.0311
_refine_ls_R_factor_gt           0.0309
_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)+(0.0430P)²+0.3680P]
 where P=(Fo²+2Fc²)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0844
_refine_ls_wR_factor_ref         0.0846
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1134
_reflns_number_total             1143
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            cg501132d_si_001.cif
_cod_data_source_block           25Fpba_2
_cod_depositor_comments
'Adding full bibliography for 4512180--4512187.cif.'
_cod_original_cell_volume        652.682(19)
_cod_database_code               4512185
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_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
F1 F 0.4056(2) 0.60121(16) 0.10186(2) 0.0214(3) Uani 1 1 d .
F2 F 0.9207(2) 1.30339(17) 0.21424(2) 0.0227(3) Uani 1 1 d .
O1 O 0.8397(3) 0.7836(2) 0.03566(3) 0.0220(3) Uani 1 1 d .
H1 H 0.814(5) 0.643(5) 0.0466(7) 0.033 Uiso 1 1 d R
O2 O 0.9046(3) 1.2327(2) 0.04698(3) 0.0227(3) Uani 1 1 d .
H2 H 0.975(5) 1.231(4) 0.0223(7) 0.034 Uiso 1 1 d R
C1 C 0.7307(3) 0.9743(3) 0.11238(4) 0.0153(3) Uani 1 1 d .
C2 C 0.5376(3) 0.7795(3) 0.12966(4) 0.0159(3) Uani 1 1 d .
C3 C 0.4645(3) 0.7553(3) 0.17324(5) 0.0179(3) Uani 1 1 d .
H3 H 0.3276 0.6192 0.1832 0.022 Uiso 1 1 calc R
C4 C 0.5955(3) 0.9344(3) 0.20212(4) 0.0177(3) Uani 1 1 d .
H4 H 0.5531 0.9229 0.2324 0.021 Uiso 1 1 calc R
C5 C 0.7889(3) 1.1293(3) 0.18567(4) 0.0165(3) Uani 1 1 d .
C6 C 0.8567(3) 1.1552(3) 0.14205(4) 0.0165(3) Uani 1 1 d .
H6 H 0.9883 1.2949 0.1321 0.020 Uiso 1 1 calc R
B1 B 0.8246(4) 0.9945(3) 0.06265(5) 0.0175(4) Uani 1 1 d .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
F1 0.0270(5) 0.0192(5) 0.0182(4) -0.0024(3) 0.0014(3) -0.0082(3)
F2 0.0290(5) 0.0235(5) 0.0155(4) -0.0054(3) 0.0019(3) -0.0055(4)
O1 0.0396(6) 0.0117(6) 0.0146(5) 0.0008(4) 0.0074(4) -0.0035(4)
O2 0.0405(7) 0.0142(5) 0.0134(5) -0.0003(4) 0.0095(4) -0.0025(4)
C1 0.0162(7) 0.0141(7) 0.0157(7) 0.0008(5) 0.0023(5) 0.0028(5)
C2 0.0174(7) 0.0133(7) 0.0169(7) -0.0014(5) -0.0006(5) 0.0011(5)
C3 0.0183(7) 0.0159(7) 0.0197(7) 0.0035(5) 0.0041(5) -0.0010(5)
C4 0.0200(7) 0.0196(7) 0.0135(6) 0.0026(5) 0.0035(5) 0.0038(6)
C5 0.0182(7) 0.0151(7) 0.0162(7) -0.0027(5) -0.0002(5) 0.0021(5)
C6 0.0182(7) 0.0137(7) 0.0177(7) 0.0014(5) 0.0036(5) 0.0007(5)
B1 0.0202(8) 0.0163(8) 0.0159(8) 0.0004(6) 0.0020(6) 0.0004(6)
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0090 0.0039 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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
B1 O1 H1 116.8(15)
B1 O2 H2 114.2(15)
C2 C1 C6 116.20(12)
C2 C1 B1 124.14(12)
C6 C1 B1 119.60(12)
F1 C2 C1 118.22(12)
F1 C2 C3 117.36(12)
C3 C2 C1 124.41(13)
C2 C3 H3 120.8
C2 C3 C4 118.42(13)
C4 C3 H3 120.8
C3 C4 H4 120.9
C5 C4 C3 118.15(12)
C5 C4 H4 120.9
F2 C5 C4 118.02(12)
F2 C5 C6 118.79(12)
C6 C5 C4 123.19(13)
C1 C6 H6 120.2
C5 C6 C1 119.61(13)
C5 C6 H6 120.2
O1 B1 C1 123.26(13)
O2 B1 O1 119.02(12)
O2 B1 C1 117.68(12)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
F1 C2 1.3641(16)
F2 C5 1.3646(16)
O1 H1 0.80(2)
O1 B1 1.3624(19)
O2 H2 0.81(2)
O2 B1 1.3515(19)
C1 C2 1.385(2)
C1 C6 1.3997(19)
C1 B1 1.5810(19)
C2 C3 1.379(2)
C3 H3 0.9500
C3 C4 1.386(2)
C4 H4 0.9500
C4 C5 1.377(2)
C5 C6 1.3766(19)
C6 H6 0.9500
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 C2 C3 C4 -179.95(12)
F2 C5 C6 C1 178.31(11)
C1 C2 C3 C4 -1.1(2)
C2 C1 C6 C5 0.95(19)
C2 C1 B1 O1 -27.0(2)
C2 C1 B1 O2 155.49(14)
C2 C3 C4 C5 0.8(2)
C3 C4 C5 F2 -179.22(12)
C3 C4 C5 C6 0.3(2)
C4 C5 C6 C1 -1.2(2)
C6 C1 C2 F1 179.04(11)
C6 C1 C2 C3 0.2(2)
C6 C1 B1 O1 150.29(14)
C6 C1 B1 O2 -27.25(19)
B1 C1 C2 F1 -3.61(19)
B1 C1 C2 C3 177.50(13)
B1 C1 C6 C5 -176.52(12)
