#------------------------------------------------------------------------------
#$Date: 2016-02-14 05:40:26 +0100 (dom 14 de feb de 2016) $
#$Revision: 176432 $
#$URL: svn://www.crystallography.net/cod/cif/4/50/63/4506381.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_4506381
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 H4 B2 F4 O4'
_chemical_formula_sum            'C6 H4 B2 F4 O4'
_chemical_formula_weight         237.71
_chemical_melting_point          ?
_chemical_name_systematic        'tetraflouro-1,2-phenylenediboronic acid'
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 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                 106.254(7)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   8.4258(12)
_cell_length_b                   5.0244(6)
_cell_length_c                   10.1656(14)
_cell_measurement_reflns_used    786
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      24.22
_cell_measurement_theta_min      2.75
_cell_volume                     413.16(10)
_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 0.989
_diffrn_measured_fraction_theta_max 0.989
_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  0.0412
_diffrn_reflns_av_sigmaI/netI    0.0384
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            3774
_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        27.52
_diffrn_reflns_theta_max         27.52
_diffrn_reflns_theta_min         2.78
_diffrn_source                   'rotating-anode X-ray source'
_exptl_absorpt_coefficient_mu    0.204
_exptl_absorpt_correction_T_max  0.998
_exptl_absorpt_correction_T_min  0.972
_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    1.911
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       unspecified
_exptl_crystal_F_000             236
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.480
_refine_diff_density_min         -0.360
_refine_diff_density_rms         0.109
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.109
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     86
_refine_ls_number_reflns         947
_refine_ls_number_restraints     4
_refine_ls_restrained_S_all      1.107
_refine_ls_R_factor_all          0.0758
_refine_ls_R_factor_gt           0.0554
_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)+(0.0811P)²+0.9010P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1608
_refine_ls_wR_factor_ref         0.1725
_reflns_number_gt                711
_reflns_number_total             947
_reflns_threshold_expression     >2sigma(I)
_iucr_refine_instructions_details
;
TITL BF4 in P2(1)/n
CELL  0.71073   8.4258   5.0244  10.1656   90.000  106.254   90.000
ZERR     2.00   0.0012   0.0006   0.0014    0.000    0.007    0.000
LATT   1
SYMM  1/2 - X, 1/2 + Y, 1/2 - Z
SFAC  C    H    B    O    F
UNIT  12   8    4    8    8
MERG   2
EQIV $1 -x+1, -y+1, -z+1
EQIV $2 x, y+1, z
HTAB O1 O2_$1
HTAB O2 O1_$2
HTAB O2 F2
DFIX 0.840 O1 H1A
DFIX 0.840 O1 H1B
DFIX 0.840 O2 H2A
DFIX 0.840 O2 H2B
FMAP   2
PLAN    5
ACTA
BOND   $H
CONF
LIST   3
WGHT     0.08110     0.90100
L.S.  10
TEMP  -173.19
FVAR     0.37210   0.47928
MOLE    1
C2    1    0.586509    0.310914    0.953206    11.00000    0.01748    0.01093 =
        0.01257   -0.00325    0.00282   -0.00050
C1    1    0.505736    0.503369    0.859191    11.00000    0.01572    0.01283 =
        0.00975    0.00049    0.00271   -0.00004
C3    1    0.419636    0.690529    0.912262    11.00000    0.01606    0.01375 =
        0.01077    0.00106    0.00106    0.00140
B1    3    0.505938    0.501927    0.703511    11.00000    0.01442    0.01626 =
        0.01051   -0.00018    0.00218   -0.00061
O1    4    0.517753    0.271569    0.639208    11.00000    0.03053    0.01598 =
        0.01292   -0.00262    0.00737    0.00002
O2    4    0.494172    0.732418    0.633688    11.00000    0.03155    0.01499 =
        0.01586    0.00294    0.00884    0.00088
F1    5    0.673543    0.118390    0.913567    11.00000    0.02267    0.01763 =
        0.01314   -0.00063    0.00644    0.00494
F2    5    0.336716    0.886677    0.830191    11.00000    0.02237    0.01576 =
        0.01193    0.00179    0.00223    0.00490
PART    1
H1A   2    0.513911    0.254004    0.556786    21.00000   -1.50000
H2A   2    0.471379    0.886215    0.652444    21.00000   -1.50000
PART    2
H1B   2    0.547189    0.117341    0.667045   -21.00000   -1.50000
H2B   2    0.489491    0.728408    0.551802   -21.00000   -1.50000
HKLF    4
END
;
_cod_data_source_file            cg3005272_si_002.cif
_cod_data_source_block           tF
_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_sg_symbol_Hall     -P2yn
_cod_original_sg_symbol_H-M      P2(1)/n
_cod_database_code               4506381
loop_
_symmetry_equiv_pos_as_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C2 C 0.5865(4) 0.3109(6) 0.9532(3) 0.0139(7) Uani 1 1 d . . .
C1 C 0.5057(4) 0.5034(6) 0.8592(3) 0.0129(7) Uani 1 1 d . . .
C3 C 0.4196(4) 0.6905(6) 0.9123(3) 0.0141(7) Uani 1 1 d . . .
B1 B 0.5059(4) 0.5019(8) 0.7035(3) 0.0140(7) Uani 1 1 d . . .
O1 O 0.5178(3) 0.2716(5) 0.6392(2) 0.0195(6) Uani 1 1 d D . .
O2 O 0.4942(3) 0.7324(5) 0.6337(2) 0.0204(6) Uani 1 1 d D . .
F1 F 0.6735(2) 0.1184(4) 0.91357(17) 0.0175(5) Uani 1 1 d . . .
F2 F 0.3367(2) 0.8867(4) 0.83019(17) 0.0172(5) Uani 1 1 d . . .
H1A H 0.514(11) 0.254(18) 0.557(3) 0.026 Uiso 0.48(5) 1 d PD A 1
H2A H 0.471(11) 0.886(8) 0.652(9) 0.026 Uiso 0.48(5) 1 d PD A 1
H1B H 0.547(10) 0.117(7) 0.667(8) 0.026 Uiso 0.52(5) 1 d PD A 2
H2B H 0.489(10) 0.728(17) 0.552(3) 0.026 Uiso 0.52(5) 1 d PD A 2
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
C2 0.0175(16) 0.0109(15) 0.0126(13) -0.0033(11) 0.0028(11) -0.0005(12)
C1 0.0157(15) 0.0128(15) 0.0097(13) 0.0005(11) 0.0027(11) 0.0000(12)
C3 0.0161(15) 0.0137(16) 0.0108(13) 0.0011(11) 0.0011(11) 0.0014(12)
B1 0.0144(17) 0.0163(18) 0.0105(15) -0.0002(13) 0.0022(13) -0.0006(14)
O1 0.0305(14) 0.0160(13) 0.0129(11) -0.0026(9) 0.0074(10) 0.0000(11)
O2 0.0316(14) 0.0150(13) 0.0159(11) 0.0029(10) 0.0088(10) 0.0009(11)
F1 0.0227(10) 0.0176(10) 0.0131(9) -0.0006(7) 0.0064(7) 0.0049(8)
F2 0.0224(10) 0.0158(10) 0.0119(8) 0.0018(7) 0.0022(7) 0.0049(8)
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
F1 C2 C3 117.9(3) . 3_667
F1 C2 C1 119.8(3) . .
C3 C2 C1 122.3(3) 3_667 .
C3 C1 C2 114.3(3) . .
C3 C1 B1 122.6(3) . .
C2 C1 B1 123.0(3) . .
F2 C3 C2 117.3(3) . 3_667
F2 C3 C1 119.4(3) . .
C2 C3 C1 123.4(3) 3_667 .
O1 B1 O2 119.2(3) . .
O1 B1 C1 120.7(3) . .
O2 B1 C1 120.1(3) . .
B1 O1 H1A 126(6) . .
B1 O1 H1B 133(6) . .
H1A O1 H1B 100(8) . .
B1 O2 H2A 132(6) . .
B1 O2 H2B 119(6) . .
H2A O2 H2B 108(9) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C2 F1 1.342(4) .
C2 C3 1.383(4) 3_667
C2 C1 1.396(4) .
C1 C3 1.386(4) .
C1 B1 1.583(4) .
C3 F2 1.352(4) .
B1 O1 1.347(4) .
B1 O2 1.347(4) .
O1 H1A 0.83(2) .
O1 H1B 0.84(2) .
O2 H2A 0.83(2) .
O2 H2B 0.82(2) .
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
O1 H1A O2 0.83(2) 1.92(2) 2.748(3) 172(9) 3_666
O2 H2A O1 0.83(2) 1.99(6) 2.716(3) 146(9) 1_565
O2 H2A F2 0.83(2) 2.39(9) 2.799(3) 111(7) .
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_1
_geom_torsion_site_symmetry_4
F1 C2 C1 C3 179.8(3) . .
C3 C2 C1 C3 -0.1(5) 3_667 .
F1 C2 C1 B1 2.2(5) . .
C3 C2 C1 B1 -177.7(3) 3_667 .
C2 C1 C3 F2 180.0(3) . .
B1 C1 C3 F2 -2.4(5) . .
C2 C1 C3 C2 0.1(5) . 3_667
B1 C1 C3 C2 177.7(3) . 3_667
C3 C1 B1 O1 -148.1(3) . .
C2 C1 B1 O1 29.3(5) . .
C3 C1 B1 O2 31.9(5) . .
C2 C1 B1 O2 -150.7(3) . .
