#------------------------------------------------------------------------------
#$Date: 2016-03-24 14:34:44 +0200 (Thu, 24 Mar 2016) $
#$Revision: 179668 $
#$URL: svn://www.crystallography.net/cod/cif/4/51/21/4512186.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_4512186
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 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   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                 93.974(8)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   4.9578(4)
_cell_length_b                   5.5256(4)
_cell_length_c                   23.484(2)
_cell_measurement_reflns_used    1905
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      66.9100
_cell_measurement_theta_min      3.7820
_cell_volume                     641.79(9)
_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 0.974
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini ultra'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0661326000
_diffrn_orient_matrix_UB_12      -0.1503019000
_diffrn_orient_matrix_UB_13      0.0524912000
_diffrn_orient_matrix_UB_21      0.1708055000
_diffrn_orient_matrix_UB_22      0.1741443000
_diffrn_orient_matrix_UB_23      0.0390117000
_diffrn_orient_matrix_UB_31      -0.2518420000
_diffrn_orient_matrix_UB_32      0.1576091000
_diffrn_orient_matrix_UB_33      0.0069538000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0352
_diffrn_reflns_av_unetI/netI     0.0224
_diffrn_reflns_Laue_measured_fraction_full 0.974
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            4609
_diffrn_reflns_point_group_measured_fraction_full 0.974
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         66.463
_diffrn_reflns_theta_min         3.774
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'Enhance Ultra (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.364
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.60551
_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    1.634
_exptl_crystal_description       plate
_exptl_crystal_F_000             320
_exptl_crystal_recrystallization_method
'crysallized from water with glutamine (1:1 molar ration)'
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.01
_refine_diff_density_max         0.367
_refine_diff_density_min         -0.297
_refine_diff_density_rms         0.075
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.134
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     106
_refine_ls_number_reflns         1124
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.134
_refine_ls_R_factor_all          0.0503
_refine_ls_R_factor_gt           0.0466
_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)+(0.0805P)²+0.4372P]
 where P=(Fo²+2Fc²)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1364
_refine_ls_wR_factor_ref         0.1398
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1015
_reflns_number_total             1124
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            cg501132d_si_001.cif
_cod_data_source_block           25Fpba_1
_cod_depositor_comments
'Adding full bibliography for 4512180--4512187.cif.'
_cod_original_cell_volume        641.80(8)
_cod_database_code               4512186
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_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 1.4324(3) 0.3463(2) 0.06179(5) 0.0255(4) Uani 1 1 d .
F2 F 0.8031(3) 0.3372(2) 0.24131(5) 0.0277(4) Uani 1 1 d .
O1 O 1.2185(3) 0.7993(3) 0.02631(7) 0.0239(4) Uani 1 1 d .
H1 H 1.364(7) 0.748(6) 0.0342(13) 0.036 Uiso 1 1 d R
O2 O 0.7843(3) 0.8419(3) 0.05787(7) 0.0221(4) Uani 1 1 d .
H2 H 0.784(6) 0.943(6) 0.0352(13) 0.033 Uiso 1 1 d R
C1 C 1.0763(4) 0.5248(4) 0.10836(8) 0.0177(5) Uani 1 1 d .
C2 C 1.2687(4) 0.3463(4) 0.10626(9) 0.0189(5) Uani 1 1 d .
C3 C 1.3109(5) 0.1637(4) 0.14607(10) 0.0225(5) Uani 1 1 d .
H3 H 1.4462 0.0443 0.1421 0.027 Uiso 1 1 calc R
C4 C 1.1493(4) 0.1601(4) 0.19202(9) 0.0225(5) Uani 1 1 d .
H4 H 1.1706 0.0375 0.2203 0.027 Uiso 1 1 calc R
C5 C 0.9578(4) 0.3381(4) 0.19553(9) 0.0205(5) Uani 1 1 d .
C6 C 0.9147(4) 0.5179(4) 0.15516(8) 0.0189(5) Uani 1 1 d .
H6 H 0.7774 0.6355 0.1590 0.023 Uiso 1 1 calc R
B1 B 1.0275(5) 0.7300(4) 0.06181(10) 0.0185(5) 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 0.0251(7) 0.0227(7) 0.0299(7) 0.0019(5) 0.0111(5) 0.0047(5)
F2 0.0373(8) 0.0221(7) 0.0251(7) 0.0033(5) 0.0127(6) 0.0010(5)
O1 0.0188(8) 0.0247(8) 0.0288(9) 0.0092(6) 0.0068(6) 0.0045(6)
O2 0.0180(8) 0.0208(8) 0.0281(8) 0.0092(6) 0.0050(6) 0.0017(6)
C1 0.0184(10) 0.0144(10) 0.0202(10) 0.0005(8) 0.0000(8) -0.0015(8)
C2 0.0167(10) 0.0178(10) 0.0224(10) -0.0019(8) 0.0030(8) -0.0022(7)
C3 0.0219(11) 0.0147(10) 0.0306(12) 0.0002(8) 0.0005(9) 0.0027(8)
C4 0.0258(12) 0.0162(10) 0.0250(11) 0.0025(8) -0.0018(9) -0.0024(8)
C5 0.0250(11) 0.0173(11) 0.0196(10) -0.0010(8) 0.0045(8) -0.0046(8)
C6 0.0184(10) 0.0147(10) 0.0237(11) -0.0016(8) 0.0025(8) 0.0010(8)
B1 0.0185(11) 0.0161(11) 0.0209(11) 0.0006(9) 0.0016(8) -0.0011(9)
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 115(2)
B1 O2 H2 110(2)
C2 C1 C6 116.29(18)
C2 C1 B1 124.22(19)
C6 C1 B1 119.49(18)
F1 C2 C1 118.51(17)
F1 C2 C3 116.58(18)
C1 C2 C3 124.9(2)
C2 C3 H3 121.0
C2 C3 C4 117.91(19)
C4 C3 H3 121.0
C3 C4 H4 120.8
C5 C4 C3 118.37(19)
C5 C4 H4 120.8
F2 C5 C4 118.27(18)
F2 C5 C6 118.42(18)
C4 C5 C6 123.3(2)
C1 C6 H6 120.4
C5 C6 C1 119.20(18)
C5 C6 H6 120.4
O1 B1 C1 123.10(19)
O2 B1 O1 119.02(19)
O2 B1 C1 117.87(18)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
F1 C2 1.366(2)
F2 C5 1.363(2)
O1 H1 0.78(3)
O1 B1 1.359(3)
O2 H2 0.77(3)
O2 B1 1.353(3)
C1 C2 1.376(3)
C1 C6 1.405(3)
C1 B1 1.582(3)
C2 C3 1.381(3)
C3 H3 0.9500
C3 C4 1.388(3)
C4 H4 0.9500
C4 C5 1.373(3)
C5 C6 1.379(3)
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 179.45(17)
F2 C5 C6 C1 178.61(16)
C1 C2 C3 C4 -0.6(3)
C2 C1 C6 C5 0.4(3)
C2 C1 B1 O1 -22.2(3)
C2 C1 B1 O2 158.4(2)
C2 C3 C4 C5 -0.3(3)
C3 C4 C5 F2 -178.67(17)
C3 C4 C5 C6 1.2(3)
C4 C5 C6 C1 -1.3(3)
C6 C1 C2 F1 -179.51(16)
C6 C1 C2 C3 0.5(3)
C6 C1 B1 O1 158.41(19)
C6 C1 B1 O2 -21.0(3)
B1 C1 C2 F1 1.1(3)
B1 C1 C2 C3 -178.9(2)
B1 C1 C6 C5 179.85(18)
