#------------------------------------------------------------------------------
#$Date: 2016-02-14 06:40:26 +0200 (Sun, 14 Feb 2016) $
#$Revision: 176432 $
#$URL: svn://www.crystallography.net/cod/cif/4/50/63/4506380.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_4506380
loop_
_publ_author_name
'Durka, Krzysztof'
'Jarzembska, Katarzyna N.'
'Kamiński, Radosław'
'Luliński, Sergiusz'
'Serwatowski, Janusz'
'Woźniak, Krzysztof'
_publ_section_title
;
 Structural and Energetic Landscape of Fluorinated 1,4-Phenylenediboronic
 Acids
;
_journal_issue                   7
_journal_name_full               'Crystal Growth & Design'
_journal_page_first              3720
_journal_paper_doi               10.1021/cg3005272
_journal_volume                  12
_journal_year                    2012
_chemical_formula_moiety         'C6 H6 B2 F2 O4'
_chemical_formula_sum            'C6 H6 B2 F2 O4'
_chemical_formula_weight         201.73
_chemical_melting_point          ?
_chemical_name_systematic        '2,5-difluoro-1,4-phenylenediboronic acid'
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                74.671(11)
_cell_angle_beta                 84.636(10)
_cell_angle_gamma                89.000(10)
_cell_formula_units_Z            1
_cell_length_a                   4.9838(19)
_cell_length_b                   5.2569(19)
_cell_length_c                   7.423(3)
_cell_measurement_reflns_used    622
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      28.157
_cell_measurement_theta_min      4.020
_cell_volume                     186.73(12)
_computing_cell_refinement       'Bruker APEX2 software'
_computing_data_collection       'Bruker APEX2 software'
_computing_data_reduction
;
 SAINT intergration software, Bruker AXS
 SORTAV, R. H. Blessing, Acta Cryst., 1995, A51, 33
;
_computing_structure_refinement
;
 SHELXS-97, G. M. Sheldrick, Acta. Cryst., 2008, A64, 112
;
_computing_structure_solution
;
 SHELXS-97, G. M. Sheldrick, Acta. Cryst., 2008, A64, 112
;
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'APEXII CCD camera'
_diffrn_measured_fraction_theta_full 0.987
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_device       'κ-geometry diffractometer'
_diffrn_measurement_device_type  'Bruker APEXII'
_diffrn_measurement_method       'omega scans'
_diffrn_orient_matrix_type       'X-axis to radiation source'
_diffrn_radiation_monochromator  'multi-layer optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_source         'TXS rotating anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0429
_diffrn_reflns_av_sigmaI/netI    0.0593
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            2255
_diffrn_reflns_reduction_process
;
 Scaled and merged with SORTAV
 R. H. Blessing, Cryst. Rev., 1987, 1, 3
 R. H. Blessing, J. Appl. Cryst., 1989, 22, 396
;
_diffrn_reflns_theta_full        27.98
_diffrn_reflns_theta_max         27.98
_diffrn_reflns_theta_min         2.86
_diffrn_source                   'rotating-anode X-ray source'
_exptl_absorpt_coefficient_mu    0.171
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.4508
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
 R. H. Blessing, Acta Cryst., 1995, A51, 33
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.794
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       unspecified
_exptl_crystal_F_000             102
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.558
_refine_diff_density_min         -0.533
_refine_diff_density_rms         0.127
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.073
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     64
_refine_ls_number_reflns         957
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.073
_refine_ls_R_factor_all          0.0940
_refine_ls_R_factor_gt           0.0645
_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)+(0.1195P)²+0.0452P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1719
_refine_ls_wR_factor_ref         0.1988
_reflns_number_gt                670
_reflns_number_total             901
_reflns_threshold_expression     >2sigma(I)
_iucr_refine_instructions_details
;
TITL BF2 in P-1
CELL  0.71073   4.9838   5.2569   7.4226   74.671   84.636   89.000
ZERR     1.00   0.0019   0.0019   0.0026    0.011    0.010    0.010
LATT   1
SFAC  C    H    B    O    F
UNIT  6    6    2    4    2
MERG   2
EQIV $1 x-1, y, z
EQIV $2 -x+1, -y+2, -z+1
HTAB O2 O1_$1
HTAB O1 O2_$2
FMAP   2
PLAN    5
ACTA
BOND   $H
CONF
LIST   3
WGHT     0.11950     0.04520
L.S.  10
TEMP  -173.10
FVAR     0.51662
MOLE    1
F1    5    0.111480    0.407435    0.289149    11.00000    0.01778    0.02823 =
        0.02443   -0.01366    0.00436   -0.00580
O2    4    0.305666    0.819042    0.415627    11.00000    0.01515    0.02973 =
        0.02870   -0.01881   -0.00067   -0.00361
AFIX   83
H2    2    0.165612    0.767499    0.380667    11.00000   -1.50000
AFIX    0
O1    4    0.761537    0.900126    0.310357    11.00000    0.01314    0.03119 =
        0.03083   -0.02021   -0.00066   -0.00290
AFIX   83
H1    2    0.736519    1.005954    0.377461    11.00000   -1.50000
AFIX    0
C1    1    0.509762    0.636811    0.142112    11.00000    0.01348    0.01854 =
        0.02170   -0.01004   -0.00310    0.00068
C3    1    0.705912    0.679171   -0.009444    11.00000    0.01479    0.01947 =
        0.02240   -0.00871   -0.00198   -0.00129
AFIX   43
H3    2    0.848891    0.800990   -0.020199    11.00000   -1.20000
AFIX    0
C2    1    0.308592    0.456666    0.143744    11.00000    0.01141    0.02143 =
        0.02050   -0.00840    0.00157   -0.00169
B1    3    0.522523    0.790285    0.296436    11.00000    0.01337    0.01787 =
        0.02206   -0.00809   -0.00243   -0.00019
HKLF    4
END
;
_cod_data_source_file            cg3005272_si_002.cif
_cod_data_source_block           25dF
_cod_depositor_comments
;
The following automatic conversions were performed:

'_chemical_melting_point' value 'not measured' was changed to '?' -
the value is undefined or not given.

'_diffrn_radiation_probe' value
'X-ray' changed to 'x-ray' according to
/home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1891 2012-01-12 08:04:46Z andrius 
;
_cod_original_cell_volume        186.72(12)
_cod_original_sg_symbol_Hall     -P1
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               4506380
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
F1 F 0.1115(3) 0.4074(3) 0.2891(2) 0.0225(5) Uani 1 1 d .
O2 O 0.3057(4) 0.8190(4) 0.4156(3) 0.0225(6) Uani 1 1 d .
H2 H 0.1656 0.7675 0.3807 0.034 Uiso 1 1 calc R
O1 O 0.7615(4) 0.9001(4) 0.3104(3) 0.0228(6) Uani 1 1 d .
H1 H 0.7365 1.0060 0.3775 0.034 Uiso 1 1 calc R
C1 C 0.5098(5) 0.6368(5) 0.1421(3) 0.0169(6) Uani 1 1 d .
C3 C 0.7059(5) 0.6792(6) -0.0094(4) 0.0182(6) Uani 1 1 d .
H3 H 0.8489 0.8010 -0.0202 0.022 Uiso 1 1 calc R
C2 C 0.3086(5) 0.4567(6) 0.1437(3) 0.0174(6) Uani 1 1 d .
B1 B 0.5225(6) 0.7903(6) 0.2964(4) 0.0172(7) 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 0.0178(8) 0.0282(11) 0.0244(8) -0.0137(7) 0.0044(6) -0.0058(7)
O2 0.0151(10) 0.0297(13) 0.0287(10) -0.0188(9) -0.0007(7) -0.0036(8)
O1 0.0131(10) 0.0312(14) 0.0308(10) -0.0202(9) -0.0007(7) -0.0029(8)
C1 0.0135(12) 0.0185(16) 0.0217(12) -0.0100(11) -0.0031(9) 0.0007(11)
C3 0.0148(13) 0.0195(15) 0.0224(12) -0.0087(10) -0.0020(9) -0.0013(11)
C2 0.0114(12) 0.0214(16) 0.0205(12) -0.0084(11) 0.0016(9) -0.0017(10)
B1 0.0134(13) 0.0179(17) 0.0221(13) -0.0081(12) -0.0024(10) -0.0002(11)
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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
B1 O2 H2 109.5 . .
B1 O1 H1 109.5 . .
C2 C1 C3 115.6(2) . .
C2 C1 B1 124.0(2) . .
C3 C1 B1 120.4(2) . .
C2 C3 C1 119.6(2) 2_665 .
C2 C3 H3 120.2 2_665 .
C1 C3 H3 120.2 . .
F1 C2 C3 117.2(2) . 2_665
F1 C2 C1 118.1(2) . .
C3 C2 C1 124.8(2) 2_665 .
O1 B1 O2 118.7(2) . .
O1 B1 C1 118.0(2) . .
O2 B1 C1 123.3(2) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
F1 C2 1.364(3) .
O2 B1 1.364(3) .
O2 H2 0.8400 .
O1 B1 1.357(3) .
O1 H1 0.8400 .
C1 C2 1.388(4) .
C1 C3 1.393(4) .
C1 B1 1.572(4) .
C3 C2 1.379(4) 2_665
C3 H3 0.9500 .
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O2 H2 O1 0.84 2.18 2.885(3) 141.0 1_455
O1 H1 O2 0.84 1.98 2.806(3) 166.4 2_676
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
_geom_torsion_site_symmetry_4
C2 C1 C3 C2 -0.5(4) 2_665
B1 C1 C3 C2 -179.9(2) 2_665
C3 C1 C2 F1 179.9(2) .
B1 C1 C2 F1 -0.8(4) .
C3 C1 C2 C3 0.6(5) 2_665
B1 C1 C2 C3 179.9(3) 2_665
C2 C1 B1 O1 161.5(3) .
C3 C1 B1 O1 -19.3(4) .
C2 C1 B1 O2 -18.9(5) .
C3 C1 B1 O2 160.4(3) .
