#------------------------------------------------------------------------------
#$Date: 2017-10-13 10:03:29 +0200 (vie 13 de oct de 2017) $
#$Revision: 201974 $
#$URL: svn://www.crystallography.net/cod/cif/2/21/06/2210655.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2210655
loop_
_publ_author_name
'Ya-Ming Wu'
'Chang-Chuan Dong'
'Shan Liu'
'Hong-Jun Zhu'
'Yi-Zu Wu'
_publ_section_title
;
 3-Fluorophenylboronic acid
;
_journal_coeditor_code           HK2115
_journal_issue                   10
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o4236
_journal_page_last               o4237
_journal_paper_doi               10.1107/S1600536806034763
_journal_volume                  62
_journal_year                    2006
_chemical_formula_iupac          'C6 H6 B F O2'
_chemical_formula_moiety         'C6 H6 B F O2'
_chemical_formula_sum            'C6 H6 B F O2'
_chemical_formula_weight         139.92
_chemical_name_systematic
;
3-Fluorophenylboronic acid
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_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           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 91.19(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   5.7560(12)
_cell_length_b                   5.0270(10)
_cell_length_c                   22.402(5)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    294(2)
_cell_measurement_theta_max      12
_cell_measurement_theta_min      10
_cell_volume                     648.1(2)
_computing_cell_refinement       'CAD-4 Software'
_computing_data_collection       'CAD-4 Software (Enraf--Nonius, 1985)'
_computing_data_reduction        'XCAD4 (Harms & Wocadlo, 1995)'
_computing_molecular_graphics    'SHELXTL (Bruker, 2000)'
_computing_publication_material  SHELXTL
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      294(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Enraf--Nonius CAD-4'
_diffrn_measurement_method       ω/2θ
_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  0.0000
_diffrn_reflns_av_sigmaI/netI    0.0304
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            1265
_diffrn_reflns_theta_full        25.95
_diffrn_reflns_theta_max         25.95
_diffrn_reflns_theta_min         1.82
_diffrn_standards_decay_%        0
_diffrn_standards_interval_time  120
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.121
_exptl_absorpt_correction_T_max  0.9880
_exptl_absorpt_correction_T_min  0.9646
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_process_details   '(North et al.,  1968)'
_exptl_crystal_colour            white
_exptl_crystal_density_diffrn    1.434
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             288
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.231
_refine_diff_density_min         -0.209
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.970
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     97
_refine_ls_number_reflns         1265
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      0.969
_refine_ls_R_factor_all          0.1053
_refine_ls_R_factor_gt           0.0843
_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/[σ²(Fo²)+(0.03P)²+2P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1812
_refine_ls_wR_factor_ref         0.1886
_reflns_number_gt                868
_reflns_number_total             1265
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            hk2115.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2210655
_cod_database_fobs_code          2210655
loop_
_symmetry_equiv_pos_as_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_refinement_flags
_atom_site_occupancy
F F 1.0010(5) -0.3535(7) 0.15299(15) 0.1001(12) Uani d . 1
O O1 0.2372(6) -0.2302(7) 0.03199(16) 0.0796(11) Uani d D 1
H H1 0.168(8) -0.216(11) -0.0018(13) 0.091 Uiso d D 1
O O2 0.1524(6) 0.2182(6) 0.04460(17) 0.0776(11) Uani d D 1
H H2 0.183(9) 0.376(5) 0.057(2) 0.091 Uiso d D 1
B B 0.2811(9) 0.0000(11) 0.0604(3) 0.0645(14) Uani d . 1
C C1 0.4737(8) 0.1904(10) 0.1573(2) 0.0713(14) Uani d . 1
H H1A 0.3539 0.3141 0.1589 0.086 Uiso calc R 1
C C2 0.6439(8) 0.1902(11) 0.2021(2) 0.0775(15) Uani d . 1
H H2B 0.6390 0.3143 0.2328 0.093 Uiso calc R 1
C C3 0.8199(8) 0.0054(10) 0.2008(2) 0.0754(15) Uani d . 1
H H3A 0.9338 0.0002 0.2308 0.090 Uiso calc R 1
C C4 0.8234(8) -0.1703(10) 0.1543(2) 0.0713(14) Uani d . 1
C C5 0.6570(7) -0.1786(10) 0.1093(2) 0.0662(12) Uani d . 1
H H5A 0.6638 -0.3063 0.0794 0.079 Uiso calc R 1
C C6 0.4775(7) 0.0088(9) 0.1096(2) 0.0610(11) Uani d . 1
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_12
_atom_site_aniso_U_13
_atom_site_aniso_U_23
F 0.0714(18) 0.100(2) 0.128(3) 0.0319(18) -0.0243(17) 0.001(2)
O1 0.090(2) 0.0527(19) 0.094(3) 0.0071(18) -0.044(2) -0.0045(19)
O2 0.080(2) 0.0468(18) 0.104(3) 0.0053(17) -0.0424(19) -0.0032(19)
B 0.061(3) 0.049(3) 0.083(4) -0.001(2) -0.022(3) 0.002(3)
C1 0.063(3) 0.057(3) 0.094(4) 0.002(2) -0.023(2) -0.003(3)
C2 0.072(3) 0.072(3) 0.088(3) -0.001(3) -0.021(3) -0.013(3)
C3 0.064(3) 0.071(3) 0.090(4) -0.005(3) -0.035(3) 0.004(3)
C4 0.055(3) 0.064(3) 0.094(4) 0.008(2) -0.015(2) 0.011(3)
C5 0.061(3) 0.062(3) 0.075(3) 0.006(2) -0.014(2) -0.002(2)
C6 0.056(2) 0.050(2) 0.076(3) -0.001(2) -0.017(2) 0.006(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'
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
B O1 H1 116(4)
B O2 H2 124(4)
O1 B O2 118.2(4)
O1 B C6 119.0(4)
O2 B C6 122.7(4)
C2 C1 C6 121.8(5)
C2 C1 H1A 119.1
C6 C1 H1A 119.1
C3 C2 C1 119.7(5)
C3 C2 H2B 120.2
C1 C2 H2B 120.2
C4 C3 C2 118.4(4)
C4 C3 H3A 120.8
C2 C3 H3A 120.8
C3 C4 C5 123.9(4)
C3 C4 F 118.1(4)
C5 C4 F 118.0(5)
C4 C5 C6 118.6(5)
C4 C5 H5A 120.7
C6 C5 H5A 120.7
C5 C6 C1 117.6(4)
C5 C6 B 120.1(4)
C1 C6 B 122.1(4)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
F C4 1.377(5)
O1 B 1.343(6)
O1 H1 0.851(19)
O2 B 1.366(6)
O2 H2 0.855(19)
B C6 1.562(6)
C1 C2 1.387(6)
C1 C6 1.406(6)
C1 H1A 0.9300
C2 C3 1.375(7)
C2 H2B 0.9300
C3 C4 1.365(7)
C3 H3A 0.9300
C4 C5 1.377(6)
C5 C6 1.398(6)
C5 H5A 0.9300
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
O1 H1 O2 3_555 0.85(3) 2.06(4) 2.796(5) 144(4) yes
O2 H2 O1 1_565 0.86(3) 2.08(3) 2.831(5) 145(4) yes
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
C6 C1 C2 C3 -1.1(8)
C1 C2 C3 C4 1.2(8)
C2 C3 C4 C5 -1.9(8)
C2 C3 C4 F 179.5(5)
C3 C4 C5 C6 2.4(8)
F C4 C5 C6 -179.0(4)
C4 C5 C6 C1 -2.1(7)
C4 C5 C6 B -178.0(5)
C2 C1 C6 C5 1.5(7)
C2 C1 C6 B 177.4(5)
O1 B C6 C5 23.3(7)
O2 B C6 C5 -156.1(5)
O1 B C6 C1 -152.5(5)
O2 B C6 C1 28.1(8)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 2015748
