#------------------------------------------------------------------------------
#$Date: 2018-01-17 08:25:43 +0200 (Wed, 17 Jan 2018) $
#$Revision: 205308 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/02/09/2020908.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_2020908
loop_
_publ_author_name
'Kopczyńska, Karolina'
'Marek, Paulina H.'
'Banaś, Bartłomiej'
'Madura, Izabela D.'
_publ_section_title
;
 Synthon preference in the cocrystal of 3,4,5-trifluorophenylboronic acid
 with urea
;
_journal_coeditor_code           LY3050
_journal_issue                   11
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              889
_journal_page_last               895
_journal_paper_doi               10.1107/S2053229617013675
_journal_volume                  73
_journal_year                    2017
_chemical_formula_iupac          'C6 H4 B F3 O2, C H4 N2 O'
_chemical_formula_moiety         'C6 H4 B F3 O2, C H4 N2 O'
_chemical_formula_sum            'C7 H8 B F3 N2 O3'
_chemical_formula_weight         235.96
_chemical_name_common
;
3,4,5-Triflurophenylboronic acid--urea (1/1)
;
_chemical_name_systematic
;
3,4,5-Triflurophenylboronic acid--carbonic diamide (1/1)
;
_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   mixed
_atom_sites_solution_primary     dual
_cell_angle_alpha                90
_cell_angle_beta                 118.304(7)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.5305(6)
_cell_length_b                   8.2823(4)
_cell_length_c                   11.5020(6)
_cell_measurement_reflns_used    3180
_cell_measurement_temperature    298.15
_cell_measurement_theta_max      66.5900
_cell_measurement_theta_min      6.8930
_cell_volume                     967.11(11)
_computing_cell_refinement
;
CrysAlis PRO (Rigaku Oxford Diffraction, 2014)
;
_computing_data_collection
;
CrysAlis PRO (Rigaku Oxford Diffraction, 2014)
;
_computing_data_reduction
;
CrysAlis PRO (Rigaku Oxford Diffraction, 2014)
;
_computing_molecular_graphics
;
DIAMOND (Crystal Impact, 2004),
CrystalExplorer (Wolff  et al., 2012),
GaussView (Dennington et al., 2009),
ORTEP-3 for Windows (Farrugia, 2012) and
Mercury (Macrae et al., 2008)
;
_computing_publication_material
;
OLEX2 (Dolomanov et al., 2009),
PLATON (Spek, 2009) and
publCIF (Westrip, 2010)
;
_computing_structure_refinement
;
SHELXL2014 (Sheldrick, 2015b)
;
_computing_structure_solution
;
SHELXT2014 (Sheldrick, 2015a)
;
_diffrn_ambient_temperature      298.15
_diffrn_detector_area_resol_mean 10.3347
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Rigaku Xcalibur Atlas Gemini ultra'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0350
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            8913
_diffrn_reflns_theta_full        67.235
_diffrn_reflns_theta_max         67.235
_diffrn_reflns_theta_min         4.355
_exptl_absorpt_coefficient_mu    1.418
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.89608
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(CrysAlis PRO; Rigaku Oxford Diffraction, 2014)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.621
_exptl_crystal_description       block
_exptl_crystal_F_000             480
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.160
_refine_diff_density_min         -0.184
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     163
_refine_ls_number_reflns         1720
_refine_ls_number_restraints     6
_refine_ls_restrained_S_all      1.040
_refine_ls_R_factor_all          0.0451
_refine_ls_R_factor_gt           0.0341
_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)+(0.0433P)²+0.2553P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0827
_refine_ls_wR_factor_ref         0.0903
_reflns_number_gt                1404
_reflns_number_total             1720
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            ly3050sup1.cif
_cod_data_source_block           I
_cod_original_cell_volume        967.11(10)
_cod_database_code               2020908
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
loop_
_space_group_symop_operation_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_occupancy
F F1 -0.05714(11) 0.39207(17) 0.22443(11) 0.0654(4) Uani d 1
F F2 -0.03799(11) 0.24804(17) 0.44331(12) 0.0645(4) Uani d 1
F F3 0.17696(13) 0.29250(16) 0.67705(11) 0.0663(4) Uani d 1
O O1 0.36346(12) 0.70035(16) 0.35408(11) 0.0433(3) Uani d 1
H H1 0.4267(17) 0.755(3) 0.361(2) 0.065 Uiso d 1
O O2 0.49688(11) 0.67205(16) 0.58143(11) 0.0402(3) Uani d 1
H H2 0.507(2) 0.641(3) 0.6532(14) 0.060 Uiso d 1
C C1 0.26752(15) 0.53300(19) 0.46804(16) 0.0334(4) Uani d 1
C C2 0.15370(16) 0.5095(2) 0.34767(17) 0.0389(4) Uani d 1
H H2A 0.1462 0.5582 0.2716 0.047 Uiso calc 1
C C3 0.05331(16) 0.4154(2) 0.34085(18) 0.0421(4) Uani d 1
C C4 0.06096(17) 0.3416(2) 0.45099(18) 0.0422(4) Uani d 1
C C5 0.17188(18) 0.3651(2) 0.56966(17) 0.0410(4) Uani d 1
C C6 0.27463(16) 0.4587(2) 0.58017(16) 0.0382(4) Uani d 1
H H6 0.3488 0.4726 0.6618 0.046 Uiso calc 1
B B1 0.38275(18) 0.6392(2) 0.47131(18) 0.0341(4) Uani d 1
O O3 0.54328(11) 0.89213(16) 0.33380(11) 0.0421(3) Uani d 1
N N1 0.67293(16) 0.9144(2) 0.55285(14) 0.0480(4) Uani d 1
H H1A 0.6231(19) 0.845(2) 0.565(2) 0.058 Uiso d 1
H H1B 0.7403(15) 0.956(3) 0.6186(16) 0.058 Uiso d 1
N N2 0.72171(16) 1.0540(2) 0.41034(16) 0.0498(4) Uani d 1
H H2B 0.694(2) 1.084(3) 0.3292(12) 0.060 Uiso d 1
H H2C 0.7894(16) 1.095(3) 0.4762(17) 0.060 Uiso d 1
C C7 0.64197(16) 0.9517(2) 0.42884(16) 0.0348(4) Uani d 1
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'
N N 0.0311 0.0180 '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
_geom_angle_publ_flag
O2 B1 O1 118.93(15) y
O1 B1 C1 116.42(15) y
O2 B1 C1 124.65(15) y
B1 O1 H1 112.5(16) ?
B1 O2 H2 119.3(17) ?
C6 C1 C2 118.02(15) y
C2 C1 B1 119.05(15) y
C6 C1 B1 122.92(14) y
C1 C2 H2A 119.7 ?
C3 C2 C1 120.55(16) ?
C3 C2 H2A 119.7 ?
F1 C3 C2 120.78(17) ?
F1 C3 C4 117.93(16) ?
C2 C3 C4 121.29(16) ?
F2 C4 C3 120.95(16) ?
F2 C4 C5 120.53(17) ?
C3 C4 C5 118.52(16) y
F3 C5 C4 117.58(15) ?
F3 C5 C6 120.66(15) ?
C4 C5 C6 121.77(16) ?
C1 C6 H6 120.1 ?
C5 C6 C1 119.84(15) ?
C5 C6 H6 120.1 ?
H1A N1 H1B 121(2) ?
C7 N1 H1A 117.6(15) ?
C7 N1 H1B 121.3(16) ?
H2B N2 H2C 123(2) ?
C7 N2 H2B 115.0(16) ?
C7 N2 H2C 121.1(16) ?
O3 C7 N1 121.14(15) y
O3 C7 N2 121.40(15) y
N1 C7 N2 117.45(16) y
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
O2 B1 1.353(2) yes
O1 B1 1.356(2) yes
C1 B1 1.579(3) yes
C1 C2 1.398(2) yes
C1 C6 1.396(2) yes
F1 C3 1.355(2) yes
F2 C4 1.347(2) yes
F3 C5 1.350(2) yes
O1 H1 0.827(10) ?
O2 H2 0.820(10) ?
C2 H2A 0.9300 ?
C2 C3 1.367(3) ?
C3 C4 1.371(3) ?
C4 C5 1.372(3) ?
C5 C6 1.372(2) ?
C6 H6 0.9300 ?
O3 C7 1.246(2) yes
N1 H1A 0.868(10) ?
N1 H1B 0.860(10) ?
N1 C7 1.332(2) yes
N2 H2B 0.867(10) ?
N2 H2C 0.860(10) ?
N2 C7 1.339(2) yes
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
O1 H1 O3 . 0.827(10) 1.899(11) 2.7084(17) 166(2)
O2 H2 O3 4_576 0.820(10) 1.933(11) 2.7427(16) 169(2)
N1 H1A O2 . 0.868(10) 2.115(10) 2.982(2) 176(2)
N2 H2B O1 2_655 0.867(10) 2.119(11) 2.975(2) 169(2)
N1 H1B F1 4_676 0.859(19) 2.41(2) 3.214(2) 155(2)
N2 H2C F1 4_676 0.86(2) 2.55(2) 3.319(2) 150(2)
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_publ_flag
F1 C3 C4 F2 0.5(3) ?
F1 C3 C4 C5 -179.57(16) ?
F2 C4 C5 F3 -0.6(3) ?
F2 C4 C5 C6 179.45(17) ?
F3 C5 C6 C1 -179.91(16) ?
C1 C2 C3 F1 -179.94(16) ?
C1 C2 C3 C4 0.0(3) ?
C2 C1 C6 C5 0.4(2) ?
C2 C1 B1 O1 -0.7(2) yes
C2 C1 B1 O2 179.33(16) yes
C2 C3 C4 F2 -179.49(17) ?
C2 C3 C4 C5 0.5(3) ?
C3 C4 C5 F3 179.46(17) ?
C3 C4 C5 C6 -0.5(3) ?
C4 C5 C6 C1 0.1(3) ?
C6 C1 C2 C3 -0.4(2) ?
C6 C1 B1 O1 178.30(16) yes
C6 C1 B1 O2 -1.7(3) yes
B1 C1 C2 C3 178.57(15) ?
B1 C1 C6 C5 -178.57(16) ?

_cod_database_fobs_code 2020908
