#------------------------------------------------------------------------------
#$Date: 2016-02-21 02:03:34 +0200 (Sun, 21 Feb 2016) $
#$Revision: 176798 $
#$URL: svn://www.crystallography.net/cod/cif/2/23/57/2235711.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_2235711
loop_
_publ_author_name
'Lin, Mu-Sen'
'Shi, Yu'
'Zhang, Shi-Yu'
'Li, Yi-Liang'
_publ_section_title
;
 1-(3-Fluorophenyl)-3-(4-nitrophenyl)urea
;
_journal_coeditor_code           ZJ2072
_journal_issue                   7
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2030
_journal_paper_doi               10.1107/S160053681202507X
_journal_volume                  68
_journal_year                    2012
_chemical_formula_iupac          'C13 H10 F N3 O3'
_chemical_formula_moiety         'C13 H10 F N3 O3'
_chemical_formula_sum            'C13 H10 F N3 O3'
_chemical_formula_weight         275.24
_chemical_name_systematic
;
1-(3-Fluorophenyl)-3-(4-nitrophenyl)urea
;
_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                 100.315(9)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.351(4)
_cell_length_b                   12.461(6)
_cell_length_c                   11.912(6)
_cell_measurement_reflns_used    4180
_cell_measurement_temperature    113(2)
_cell_measurement_theta_max      27.8
_cell_measurement_theta_min      1.6
_cell_volume                     1219.6(10)
_computing_cell_refinement       'CrystalClear (Rigaku, 2005)'
_computing_data_collection       'CrystalClear (Rigaku, 2005)'
_computing_data_reduction        'CrystalClear (Rigaku, 2005)'
_computing_molecular_graphics    'SHELXTL/PC (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL/PC (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      113(2)
_diffrn_detector_area_resol_mean 14.63
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Rigaku Saturn CCD area-detector'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  multilayer
_diffrn_radiation_source         'rotating anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0454
_diffrn_reflns_av_sigmaI/netI    0.0413
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            12466
_diffrn_reflns_theta_full        27.84
_diffrn_reflns_theta_max         27.84
_diffrn_reflns_theta_min         2.39
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.119
_exptl_absorpt_correction_T_max  0.9765
_exptl_absorpt_correction_T_min  0.9719
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   CrystalClear
_exptl_crystal_colour            Yellow
_exptl_crystal_density_diffrn    1.499
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Prism
_exptl_crystal_F_000             568
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.295
_refine_diff_density_min         -0.263
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.121
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     189
_refine_ls_number_reflns         2900
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.120
_refine_ls_R_factor_all          0.0621
_refine_ls_R_factor_gt           0.0516
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0630P)²+0.1263P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1240
_refine_ls_wR_factor_ref         0.1309
_reflns_number_gt                2459
_reflns_number_total             2900
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            zj2072.cif
_cod_data_source_block           I
_cod_original_cell_volume        1219.5(11)
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               2235711
_cod_database_fobs_code          2235711
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_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_symmetry_multiplicity
F F1 0.29184(14) 0.96861(8) -0.02312(9) 0.0449(3) Uani d . 1 1
O O1 -0.04969(14) 0.17411(10) 0.34582(10) 0.0322(3) Uani d . 1 1
O O2 0.01132(14) 0.04318(10) 0.24132(10) 0.0340(3) Uani d . 1 1
O O3 0.19105(13) 0.60131(9) 0.05581(9) 0.0277(3) Uani d . 1 1
N N1 0.01105(16) 0.13960(12) 0.26533(12) 0.0265(3) Uani d . 1 1
N N2 0.26220(16) 0.43681(11) -0.00884(11) 0.0255(3) Uani d D 1 1
N N3 0.32644(17) 0.58967(11) -0.09569(11) 0.0258(3) Uani d D 1 1
C C1 0.20093(18) 0.36633(13) 0.06336(13) 0.0236(3) Uani d . 1 1
C C2 0.19815(19) 0.25683(13) 0.03495(13) 0.0252(4) Uani d . 1 1
H H2 0.2380 0.2346 -0.0312 0.030 Uiso calc R 1 1
C C3 0.13910(19) 0.18127(13) 0.10071(14) 0.0264(4) Uani d . 1 1
H H3 0.1371 0.1074 0.0808 0.032 Uiso calc R 1 1
C C4 0.08209(18) 0.21605(13) 0.19783(13) 0.0232(3) Uani d . 1 1
C C5 0.08776(19) 0.32275(13) 0.22924(14) 0.0258(4) Uani d . 1 1
H H5 0.0505 0.3439 0.2967 0.031 Uiso calc R 1 1
C C6 0.14717(19) 0.39910(13) 0.16335(13) 0.0258(4) Uani d . 1 1
H H6 0.1517 0.4725 0.1852 0.031 Uiso calc R 1 1
C C7 0.25437(18) 0.54780(13) -0.01016(13) 0.0234(3) Uani d . 1 1
C C8 0.35025(18) 0.69898(13) -0.11978(13) 0.0246(4) Uani d . 1 1
C C9 0.42473(19) 0.72135(14) -0.21284(14) 0.0268(4) Uani d . 1 1
H H9 0.4554 0.6642 -0.2573 0.032 Uiso calc R 1 1
C C10 0.4543(2) 0.82664(14) -0.24089(14) 0.0297(4) Uani d . 1 1
H H10 0.5056 0.8406 -0.3044 0.036 Uiso calc R 1 1
C C11 0.4106(2) 0.91169(15) -0.17805(15) 0.0327(4) Uani d . 1 1
H H11 0.4305 0.9840 -0.1969 0.039 Uiso calc R 1 1
C C12 0.3367(2) 0.88660(13) -0.08702(15) 0.0307(4) Uani d . 1 1
C C13 0.30351(19) 0.78355(14) -0.05540(14) 0.0274(4) Uani d . 1 1
H H13 0.2509 0.7705 0.0077 0.033 Uiso calc R 1 1
H H2A 0.314(2) 0.4069(14) -0.0618(13) 0.037(5) Uiso d D 1 1
H H3A 0.372(2) 0.5429(15) -0.1377(15) 0.056(7) Uiso d D 1 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
O2 N1 O1 122.33(14)
O2 N1 C4 119.72(14)
O1 N1 C4 117.95(14)
C7 N2 C1 128.07(14)
C7 N2 H2A 115.5(12)
C1 N2 H2A 116.4(12)
C7 N3 C8 127.73(14)
C7 N3 H3A 116.9(14)
C8 N3 H3A 115.1(14)
N2 C1 C2 117.18(14)
N2 C1 C6 123.33(15)
C2 C1 C6 119.47(15)
C3 C2 C1 121.41(15)
C3 C2 H2 119.3
C1 C2 H2 119.3
C2 C3 C4 118.09(15)
C2 C3 H3 121.0
C4 C3 H3 121.0
C5 C4 C3 121.57(15)
C5 C4 N1 118.89(14)
C3 C4 N1 119.51(15)
C4 C5 C6 120.54(15)
C4 C5 H5 119.7
C6 C5 H5 119.7
C5 C6 C1 118.87(16)
C5 C6 H6 120.6
C1 C6 H6 120.6
O3 C7 N3 124.54(16)
O3 C7 N2 124.28(15)
N3 C7 N2 111.18(14)
C9 C8 C13 119.58(15)
C9 C8 N3 116.97(15)
C13 C8 N3 123.46(15)
C10 C9 C8 120.35(16)
C10 C9 H9 119.8
C8 C9 H9 119.8
C11 C10 C9 121.22(16)
C11 C10 H10 119.4
C9 C10 H10 119.4
C12 C11 C10 116.83(16)
C12 C11 H11 121.6
C10 C11 H11 121.6
F1 C12 C11 118.40(15)
F1 C12 C13 117.07(15)
C11 C12 C13 124.52(16)
C12 C13 C8 117.49(16)
C12 C13 H13 121.3
C8 C13 H13 121.3
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
F1 C12 1.366(2)
O1 N1 1.2392(18)
O2 N1 1.235(2)
O3 C7 1.2209(19)
N1 C4 1.441(2)
N2 C7 1.384(2)
N2 C1 1.389(2)
N2 H2A 0.907(9)
N3 C7 1.376(2)
N3 C8 1.413(2)
N3 H3A 0.897(9)
C1 C2 1.405(2)
C1 C6 1.407(2)
C2 C3 1.372(2)
C2 H2 0.9500
C3 C4 1.397(2)
C3 H3 0.9500
C4 C5 1.380(2)
C5 C6 1.381(2)
C5 H5 0.9500
C6 H6 0.9500
C8 C9 1.393(2)
C8 C13 1.399(2)
C9 C10 1.387(2)
C9 H9 0.9500
C10 C11 1.384(2)
C10 H10 0.9500
C11 C12 1.376(3)
C11 H11 0.9500
C12 C13 1.380(2)
C13 H13 0.9500
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
N2 H2A O1 4_665 0.907(9) 1.993(10) 2.890(2) 169.5(17)
N3 H3A O2 4_665 0.897(9) 2.275(10) 3.157(2) 168(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
C7 N2 C1 C2 168.79(15)
C7 N2 C1 C6 -13.1(2)
N2 C1 C2 C3 -179.65(14)
C6 C1 C2 C3 2.2(2)
C1 C2 C3 C4 -0.3(2)
C2 C3 C4 C5 -1.5(2)
C2 C3 C4 N1 176.62(13)
O2 N1 C4 C5 -176.89(14)
O1 N1 C4 C5 3.6(2)
O2 N1 C4 C3 4.9(2)
O1 N1 C4 C3 -174.56(13)
C3 C4 C5 C6 1.5(2)
N1 C4 C5 C6 -176.63(14)
C4 C5 C6 C1 0.4(2)
N2 C1 C6 C5 179.79(14)
C2 C1 C6 C5 -2.1(2)
C8 N3 C7 O3 4.1(3)
C8 N3 C7 N2 -176.20(14)
C1 N2 C7 O3 0.8(3)
C1 N2 C7 N3 -178.89(14)
C7 N3 C8 C9 -179.05(15)
C7 N3 C8 C13 1.1(3)
C13 C8 C9 C10 0.8(2)
N3 C8 C9 C10 -179.09(14)
C8 C9 C10 C11 -0.2(2)
C9 C10 C11 C12 0.0(2)
C10 C11 C12 F1 -179.98(14)
C10 C11 C12 C13 -0.3(3)
F1 C12 C13 C8 -179.49(14)
C11 C12 C13 C8 0.8(3)
C9 C8 C13 C12 -1.0(2)
N3 C8 C13 C12 178.82(15)
