Hydrogen-Bonded Dimeric Synthon of Fluoro-Substituted Phenylboronic Acids versus Supramolecular Organization in Crystals
Madura, Izabela D.; Czerwińska, Karolina; Sołdańska, Dominika; Crystal Growth & Design 14 (2014) 5912–; doi:10.1021/cg501132d

data_4512180
_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 &amp; Design'
_journal_page_first              5912
_journal_paper_doi               10.1021/cg501132d
_journal_volume                  14
_journal_year                    2014
_chemical_formula_moiety         'C6 H6 B F O2'
_chemical_formula_sum            'C6 H6 B F O2'
_chemical_formula_weight         139.92
_chemical_name_common            'o-fluorophenylboronic acid'
_chemical_name_systematic        '2-fluorophenylboronic 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   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method
;
Olex2 1.2-beta
(compiled 2013.12.10 svn.r2850 for OlexSys, GUI svn.r4736)
;
_cell_angle_alpha                90.00
_cell_angle_beta                 94.731(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   5.10172(16)
_cell_length_b                   5.55660(17)
_cell_length_c                   22.0587(7)
_cell_measurement_reflns_used    3919
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      66.8631
_cell_measurement_theta_min      4.0207
_cell_volume                     623.19(3)
_computing_cell_refinement
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.52 (release 06-11-2009 CrysAlis171 .NET)
(compiled Nov  6 2009,16:24:50)
;
_computing_data_collection
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.52 (release 06-11-2009 CrysAlis171 .NET)
(compiled Nov  6 2009,16:24:50)
;
_computing_data_reduction
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.52 (release 06-11-2009 CrysAlis171 .NET)
(compiled Nov  6 2009,16:24:50)
;
_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_area_resol_mean 10.3347
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details
;
  1 omega  -35.00   60.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       40.9488  -37.0000  -90.0000 95

  2 omega   15.00   93.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       40.9488 -125.0000   60.0000 78

  3 omega  135.00  161.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       93.5000  125.0000  -30.0000 26

  4 omega  140.00  165.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       93.5000   15.0000 -120.0000 25

  5 omega   70.00  115.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       93.5000  -77.0000   30.0000 45

  6 omega   61.00  105.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       93.5000   70.0000  160.0000 44

  7 omega   14.00   57.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       93.5000 -107.0000  -42.0000 43

  8 omega   55.00  123.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       93.5000  -61.0000  -66.0000 68

  9 omega  109.00  164.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       93.5000   45.0000  -90.0000 55

 10 omega   97.00  128.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       93.5000  -90.0000   -4.0000 31

 11 omega   62.00  108.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       93.5000   77.0000 -150.0000 46

 12 omega  124.00  165.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       93.5000   77.0000 -150.0000 41

 13 omega   74.00  106.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       93.5000  125.0000   60.0000 32

 14 omega  142.00  168.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       93.5000  125.0000   60.0000 26

 15 omega  102.00  128.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       93.5000   45.0000    0.0000 26

 16 omega   40.00  114.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       93.5000   15.0000 -120.0000 74

 17 omega   76.00  105.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       93.5000  125.0000  -30.0000 29

 18 omega    7.00  120.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       40.9488   77.0000   30.0000 113

 19 omega    9.00  117.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       40.9488   70.0000  160.0000 108

 20 omega    7.00  120.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       40.9488   77.0000  -90.0000 113

 21 omega -168.00  -57.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -90.0000  -75.0000  100.0000 111

 22 omega   66.00  103.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       93.5000   45.0000  -30.0000 37

 23 omega   19.00   77.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       93.5000  -45.0000  120.0000 58
;
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini ultra'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0519264333
_diffrn_orient_matrix_UB_12      -0.0184057693
_diffrn_orient_matrix_UB_13      -0.0676322319
_diffrn_orient_matrix_UB_21      -0.1855792869
_diffrn_orient_matrix_UB_22      -0.2184411167
_diffrn_orient_matrix_UB_23      -0.0073642184
_diffrn_orient_matrix_UB_31      -0.2336258024
_diffrn_orient_matrix_UB_32      0.1691416105
_diffrn_orient_matrix_UB_33      -0.0167900501
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0203
_diffrn_reflns_av_unetI/netI     0.0172
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            4732
_diffrn_reflns_theta_full        67.03
_diffrn_reflns_theta_max         67.03
_diffrn_reflns_theta_min         4.02
_diffrn_source                   'Enhance Ultra (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.085
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.59559
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.52 (release 06-11-2009 CrysAlis171 .NET)
(compiled Nov  6 2009,16:24:50)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_density_diffrn    1.491
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             288
_exptl_crystal_size_max          0.6
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.501
_refine_diff_density_min         -0.183
_refine_diff_density_rms         0.046
_refine_ls_extinction_coef       0.0161(17)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.088
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     100
_refine_ls_number_reflns         1104
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.088
_refine_ls_R_factor_all          0.0354
_refine_ls_R_factor_gt           0.0343
_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/[\s^2^(Fo^2^)+(0.0474P)^2^+0.3828P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0920
_refine_ls_wR_factor_ref         0.0930
_reflns_number_gt                1068
_reflns_number_total             1104
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            cg501132d_si_001.cif
_cod_data_source_block           2Fpba
_cod_depositor_comments
'Adding full bibliography for 4512180--4512187.cif.'
_cod_database_code               4512180