#------------------------------------------------------------------------------
#$Date: 2025-08-19 16:18:28 +0300 (Tue, 19 Aug 2025) $
#$Revision: 301805 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/62/2226217.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_2226217
loop_
_publ_author_name
'Loh, Wan-Sin'
'Fun, Hoong-Kun'
'Sarveswari, S.'
'Vijayakumar, V.'
'Ragavan, R. Venkat'
_publ_section_title
;
 N,N'-Bis(4-fluorophenyl)urea
;
_journal_coeditor_code           LH5040
_journal_issue                   6
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1319
_journal_paper_doi               10.1107/S1600536810016399
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C13 H10 F2 N2 O'
_chemical_formula_moiety         'C13 H10 F2 N2 O'
_chemical_formula_sum            'C13 H10 F2 N2 O'
_chemical_formula_weight         248.23
_chemical_name_systematic
;
N,N'-Bis(4-fluorophenyl)urea
;
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/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                 95.969(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            12
_cell_length_a                   67.541(4)
_cell_length_b                   4.5750(3)
_cell_length_c                   10.7098(6)
_cell_measurement_reflns_used    3635
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      32.07
_cell_measurement_theta_min      2.43
_cell_volume                     3291.4(3)
_computing_cell_refinement       'SAINT (Bruker, 2009)'
_computing_data_collection       'APEX2 (Bruker, 2009)'
_computing_data_reduction        'SAINT (Bruker, 2009)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material
;
SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009)
;
_computing_structure_refinement  'SHELXTL (Sheldrick, 2008)'
_computing_structure_solution    'SHELXTL (Sheldrick, 2008)'
_diffrn_ambient_temperature      100.00(10)
_diffrn_measured_fraction_theta_full 0.987
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_device_type
;
Bruker APEXII DUO CCD area-detector diffractometer
;
_diffrn_measurement_method       'φ and ω scans'
_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  0.0495
_diffrn_reflns_av_sigmaI/netI    0.0490
_diffrn_reflns_limit_h_max       102
_diffrn_reflns_limit_h_min       -102
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            21915
_diffrn_reflns_theta_full        32.72
_diffrn_reflns_theta_max         32.72
_diffrn_reflns_theta_min         1.82
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.120
_exptl_absorpt_correction_T_max  0.9897
_exptl_absorpt_correction_T_min  0.9323
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2009)'
_exptl_crystal_colour            brown
_exptl_crystal_density_diffrn    1.503
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1536
_exptl_crystal_size_max          0.59
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.09
_refine_diff_density_max         0.686
_refine_diff_density_min         -0.507
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     257
_refine_ls_number_reflns         5986
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.047
_refine_ls_R_factor_all          0.0721
_refine_ls_R_factor_gt           0.0483
_refine_ls_shift/su_max_lt       0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0899P)²+0.1948P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1377
_refine_ls_wR_factor_ref         0.1586
_reflns_number_gt                4304
_reflns_number_total             5986
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            lh5040.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
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_enum 1527 2010-12-29 10:47:43Z saulius 
;
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               2226217
_cod_database_fobs_code          2226217
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -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
_atom_site_disorder_assembly
_atom_site_disorder_group
F F1A 0.244179(12) 0.5229(2) 0.33663(8) 0.02522(19) Uani d . 1 . .
O O1A 0.167883(13) 0.5447(2) 0.62122(9) 0.0198(2) Uani d . 1 . .
N N1A 0.180685(15) 0.9777(2) 0.55991(10) 0.0162(2) Uani d . 1 . .
N N2A 0.153498(15) 0.9743(3) 0.67129(11) 0.0175(2) Uani d . 1 . .
C C1A 0.209007(17) 0.6417(3) 0.56407(11) 0.0163(2) Uani d . 1 . .
H H1AA 0.2064 0.5746 0.6426 0.020 Uiso calc R 1 . .
C C2A 0.225076(17) 0.5295(3) 0.50863(12) 0.0180(2) Uani d . 1 . .
H H2AA 0.2332 0.3860 0.5486 0.022 Uiso calc R 1 . .
C C3A 0.228714(17) 0.6362(3) 0.39263(12) 0.0178(2) Uani d . 1 . .
C C4A 0.217243(18) 0.8517(3) 0.33077(11) 0.0184(2) Uani d . 1 . .
H H4AA 0.2203 0.9236 0.2539 0.022 Uiso calc R 1 . .
C C5A 0.200924(18) 0.9591(3) 0.38612(11) 0.0172(2) Uani d . 1 . .
H H5AA 0.1928 1.1008 0.3451 0.021 Uiso calc R 1 . .
C C6A 0.196784(16) 0.8543(3) 0.50280(10) 0.0142(2) Uani d . 1 . .
C C7A 0.167422(16) 0.8158(3) 0.61783(11) 0.0150(2) Uani d . 1 . .
C C8A 0.138631(16) 0.8455(3) 0.73842(11) 0.0154(2) Uani d . 1 . .
C C9A 0.143599(18) 0.6409(3) 0.83227(12) 0.0187(2) Uani d . 1 . .
H H9AA 0.1568 0.5838 0.8508 0.022 Uiso calc R 1 . .
C C10A 0.128905(18) 0.5208(3) 0.89873(12) 0.0207(3) Uani d . 1 . .
H H10A 0.1320 0.3818 0.9610 0.025 Uiso calc R 1 . .
C C11A 0.109514(19) 0.6143(3) 0.86946(12) 0.0209(3) Uani d . 1 . .
C C12A 0.104185(18) 0.8202(3) 0.77910(12) 0.0219(3) Uani d . 1 . .
H H12A 0.0910 0.8809 0.7630 0.026 Uiso calc R 1 . .
C C13A 0.118945(18) 0.9362(3) 0.71211(12) 0.0193(2) Uani d . 1 . .
H H13A 0.1157 1.0745 0.6497 0.023 Uiso calc R 1 . .
F F2A 0.095139(12) 0.4948(2) 0.93363(9) 0.0309(2) Uani d . 1 . .
F F1B 0.072613(12) 0.6424(2) 1.16351(8) 0.0289(2) Uani d . 1 . .
O O1B 0.0000 0.6661(3) 0.7500 0.0262(3) Uani d S 1 . .
N N1B 0.013863(16) 1.0982(3) 0.82126(11) 0.0193(2) Uani d . 1 . .
C C1B 0.024299(18) 0.7613(3) 0.99248(12) 0.0200(2) Uani d . 1 . .
H H1BA 0.0112 0.6961 0.9919 0.024 Uiso calc R 1 . .
C C2B 0.03907(2) 0.6455(3) 1.07851(12) 0.0213(3) Uani d . 1 . .
H H2BA 0.0362 0.4998 1.1343 0.026 Uiso calc R 1 . .
C C3B 0.058161(18) 0.7529(3) 1.07883(12) 0.0210(3) Uani d . 1 . .
C C4B 0.063141(18) 0.9679(3) 0.99790(12) 0.0212(3) Uani d . 1 . .
H H4BA 0.0761 1.0385 1.0018 0.025 Uiso calc R 1 . .
C C5B 0.048369(18) 1.0776(3) 0.91008(12) 0.0194(2) Uani d . 1 . .
H H5BA 0.0515 1.2200 0.8533 0.023 Uiso calc R 1 . .
C C6B 0.028914(17) 0.9741(3) 0.90722(12) 0.0170(2) Uani d . 1 . .
C C7B 0.0000 0.9380(4) 0.7500 0.0181(3) Uani d S 1 . .
H H1NA 0.1792(3) 1.157(5) 0.5567(17) 0.028(5) Uiso d . 1 . .
H H1NB 0.0136(3) 1.289(6) 0.8078(19) 0.043(6) Uiso d . 1 . .
H H2NA 0.1535(2) 1.160(4) 0.6624(16) 0.022(4) Uiso 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 0.0033 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'
N N 0.0061 0.0033 '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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C7A N1A C6A . . 123.39(11) ?
C7A N1A H1NA . . 118.3(13) ?
C6A N1A H1NA . . 118.3(13) ?
C7A N2A C8A . . 123.17(11) ?
C7A N2A H2NA . . 118.4(11) ?
C8A N2A H2NA . . 118.4(11) ?
C2A C1A C6A . . 120.49(11) ?
C2A C1A H1AA . . 119.8 ?
C6A C1A H1AA . . 119.8 ?
C3A C2A C1A . . 118.30(11) ?
C3A C2A H2AA . . 120.8 ?
C1A C2A H2AA . . 120.8 ?
F1A C3A C4A . . 118.63(11) ?
F1A C3A C2A . . 118.60(11) ?
C4A C3A C2A . . 122.77(11) ?
C3A C4A C5A . . 118.48(11) ?
C3A C4A H4AA . . 120.8 ?
C5A C4A H4AA . . 120.8 ?
C6A C5A C4A . . 120.08(12) ?
C6A C5A H5AA . . 120.0 ?
C4A C5A H5AA . . 120.0 ?
C5A C6A C1A . . 119.84(11) ?
C5A C6A N1A . . 118.94(11) ?
C1A C6A N1A . . 121.14(10) ?
O1A C7A N2A . . 122.47(11) ?
O1A C7A N1A . . 122.79(11) ?
N2A C7A N1A . . 114.74(11) ?
C9A C8A C13A . . 120.06(11) ?
C9A C8A N2A . . 121.00(10) ?
C13A C8A N2A . . 118.90(11) ?
C8A C9A C10A . . 120.28(11) ?
C8A C9A H9AA . . 119.9 ?
C10A C9A H9AA . . 119.9 ?
C11A C10A C9A . . 118.08(12) ?
C11A C10A H10A . . 121.0 ?
C9A C10A H10A . . 121.0 ?
F2A C11A C12A . . 118.92(12) ?
F2A C11A C10A . . 118.03(12) ?
C12A C11A C10A . . 123.05(12) ?
C11A C12A C13A . . 118.42(12) ?
C11A C12A H12A . . 120.8 ?
C13A C12A H12A . . 120.8 ?
C12A C13A C8A . . 120.09(12) ?
C12A C13A H13A . . 120.0 ?
C8A C13A H13A . . 120.0 ?
C7B N1B C6B . . 123.66(12) ?
C7B N1B H1NB . . 116.0(14) ?
C6B N1B H1NB . . 120.2(14) ?
C2B C1B C6B . . 120.46(11) ?
C2B C1B H1BA . . 119.8 ?
C6B C1B H1BA . . 119.8 ?
C3B C2B C1B . . 118.17(13) ?
C3B C2B H2BA . . 120.9 ?
C1B C2B H2BA . . 120.9 ?
F1B C3B C4B . . 118.73(12) ?
F1B C3B C2B . . 118.40(13) ?
C4B C3B C2B . . 122.87(12) ?
C3B C4B C5B . . 118.59(12) ?
C3B C4B H4BA . . 120.7 ?
C5B C4B H4BA . . 120.7 ?
C4B C5B C6B . . 120.01(13) ?
C4B C5B H5BA . . 120.0 ?
C6B C5B H5BA . . 120.0 ?
C1B C6B C5B . . 119.87(12) ?
C1B C6B N1B . . 120.79(11) ?
C5B C6B N1B . . 119.26(12) ?
O1B C7B N1B . 2_556 122.63(9) ?
O1B C7B N1B . . 122.63(8) ?
N1B C7B N1B 2_556 . 114.74(17) ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
F1A C3A . 1.3601(13) ?
O1A C7A . 1.2412(15) ?
N1A C7A . 1.3606(15) ?
N1A C6A . 1.4190(15) ?
N1A H1NA . 0.83(2) ?
N2A C7A . 1.3602(15) ?
N2A C8A . 1.4223(15) ?
N2A H2NA . 0.85(2) ?
C1A C2A . 1.3886(16) ?
C1A C6A . 1.3948(17) ?
C1A H1AA . 0.9300 ?
C2A C3A . 1.3805(18) ?
C2A H2AA . 0.9300 ?
C3A C4A . 1.3799(18) ?
C4A C5A . 1.3941(16) ?
C4A H4AA . 0.9300 ?
C5A C6A . 1.3937(16) ?
C5A H5AA . 0.9300 ?
C8A C9A . 1.3888(18) ?
C8A C13A . 1.3935(16) ?
C9A C10A . 1.3929(17) ?
C9A H9AA . 0.9300 ?
C10A C11A . 1.3824(18) ?
C10A H10A . 0.9300 ?
C11A F2A . 1.3611(14) ?
C11A C12A . 1.371(2) ?
C12A C13A . 1.3925(17) ?
C12A H12A . 0.9300 ?
C13A H13A . 0.9300 ?
F1B C3B . 1.3589(15) ?
O1B C7B . 1.244(2) ?
N1B C7B . 1.3593(15) ?
N1B C6B . 1.4173(16) ?
N1B H1NB . 0.88(3) ?
C1B C2B . 1.3902(18) ?
C1B C6B . 1.3921(18) ?
C1B H1BA . 0.9300 ?
C2B C3B . 1.3798(19) ?
C2B H2BA . 0.9300 ?
C3B C4B . 1.376(2) ?
C4B C5B . 1.3916(18) ?
C4B H4BA . 0.9300 ?
C5B C6B . 1.3942(17) ?
C5B H5BA . 0.9300 ?
C7B N1B 2_556 1.3593(15) ?
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
N1A H1NA O1A 1_565 0.83(2) 2.08(2) 2.8331(13) 151.7(18) yes
N1B H1NB O1B 1_565 0.89(3) 2.02(3) 2.8392(18) 153.3(19) yes
N2A H2NA O1A 1_565 0.855(18) 2.080(17) 2.8547(16) 150.5(13) yes
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139078972
