#------------------------------------------------------------------------------
#$Date: 2016-02-14 16:26:36 +0200 (Sun, 14 Feb 2016) $
#$Revision: 176435 $
#$URL: svn://www.crystallography.net/cod/cif/2/21/87/2218751.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_2218751
loop_
_publ_author_name
'Liu, Yin-hong'
'Li, Fang-shi'
'Yin, Li-he'
'Yu, Da-sheng'
_publ_section_title
;
 1-(2-Chlorobenzoyl)-3-[4-(trifluoromethoxy)phenyl]urea
;
_journal_coeditor_code           KP2174
_journal_issue                   7
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1218
_journal_paper_doi               10.1107/S1600536808016462
_journal_volume                  64
_journal_year                    2008
_chemical_formula_iupac          'C15 H10 Cl F3  N2 O3'
_chemical_formula_moiety         'C15 H10 Cl F3  N2 O3'
_chemical_formula_sum            'C15 H10 Cl F3 N2 O3'
_chemical_formula_weight         358.70
_chemical_name_common            Triflumuron
_chemical_name_systematic
;
1-(2-Chlorobenzoyl)-3-[4-(trifluoromethoxy)phenyl]urea
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90.00
_cell_angle_beta                 101.74(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   17.293(4)
_cell_length_b                   8.2870(17)
_cell_length_c                   11.073(2)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      14
_cell_measurement_theta_min      10
_cell_volume                     1553.6(6)
_computing_cell_refinement       'CAD-4 Software (Enraf--Nonius, 1989)'
_computing_data_collection       'CAD-4 Software (Enraf--Nonius, 1989)'
_computing_data_reduction        'XCAD4 (Harms & Wocadlo, 1995)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Enraf--Nonius CAD-4'
_diffrn_measurement_method       ω/2θ
_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  0.0123
_diffrn_reflns_av_sigmaI/netI    0.0229
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            2946
_diffrn_reflns_theta_full        25.19
_diffrn_reflns_theta_max         25.19
_diffrn_reflns_theta_min         1.20
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 200
_diffrn_standards_interval_time  120
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.296
_exptl_absorpt_correction_T_max  0.9433
_exptl_absorpt_correction_T_min  0.9166
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_process_details   '(North et al.,  1968)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.534
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             728
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.582
_refine_diff_density_min         -0.375
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.009
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     209
_refine_ls_number_reflns         2784
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.009
_refine_ls_R_factor_all          0.1065
_refine_ls_R_factor_gt           0.0788
_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)+(0.06P)²+3P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1711
_refine_ls_wR_factor_ref         0.1859
_reflns_number_gt                1906
_reflns_number_total             2784
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            kp2174.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_original_formula_sum        'C15 H10 Cl F3  N2 O3'
_cod_database_code               2218751
_cod_database_fobs_code          2218751
loop_
_symmetry_equiv_pos_as_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_refinement_flags
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl Cl 0.39377(8) 0.46678(16) 0.93229(10) 0.0767(4) Uani d . 1 . .
F F1 0.9765(5) 0.8806(12) 0.8631(10) 0.147 Uani d PD 0.52 A 1
F F2 0.9962(5) 0.7066(11) 0.7283(8) 0.131 Uani d P 0.52 A 1
F F3 1.0673(5) 0.7391(10) 0.9039(8) 0.127 Uani d PD 0.52 A 1
F F1' 0.9962(6) 0.8363(13) 0.9452(9) 0.145 Uani d P 0.48 A 2
F F2' 0.9788(6) 0.7985(12) 0.7564(10) 0.140 Uani d P 0.48 A 2
F F3' 1.0763(4) 0.6519(9) 0.8854(7) 0.111 Uani d P 0.48 A 2
O O1 0.9560(2) 0.6074(6) 0.8858(4) 0.1185(16) Uani d . 1 A .
O O2 0.59902(15) 0.5358(4) 0.5609(2) 0.0661(8) Uani d . 1 . .
O O3 0.50002(17) 0.7159(4) 0.8415(3) 0.0733(9) Uani d . 1 . .
N N1 0.62777(18) 0.6359(4) 0.7569(3) 0.0578(9) Uani d . 1 . .
H H1A 0.6061 0.6732 0.8145 0.069 Uiso calc R 1 . .
N N2 0.49834(18) 0.6012(4) 0.6534(3) 0.0552(8) Uani d . 1 . .
H H2A 0.4665 0.5691 0.5876 0.066 Uiso calc R 1 . .
C C1 0.9996(3) 0.7289(13) 0.8574(9) 0.146(3) Uani d . 1 . .
C C2 0.8720(3) 0.6213(7) 0.8485(5) 0.0820(15) Uani d . 1 . .
C C3 0.8311(3) 0.6917(7) 0.9265(5) 0.0849(16) Uani d . 1 A .
H H3A 0.8573 0.7353 1.0010 0.102 Uiso calc R 1 . .
C C4 0.7488(3) 0.6978(6) 0.8930(4) 0.0742(13) Uani d . 1 . .
H H4A 0.7194 0.7466 0.9445 0.089 Uiso calc R 1 A .
C C5 0.7113(2) 0.6298(5) 0.7812(3) 0.0570(10) Uani d . 1 A .
C C6 0.7545(2) 0.5566(6) 0.7047(4) 0.0694(12) Uani d . 1 . .
H H6A 0.7294 0.5092 0.6310 0.083 Uiso calc R 1 A .
C C7 0.8363(3) 0.5553(7) 0.7400(5) 0.0802(14) Uani d . 1 A .
H H7A 0.8666 0.5088 0.6888 0.096 Uiso calc R 1 . .
C C8 0.5786(2) 0.5883(5) 0.6510(4) 0.0532(10) Uani d . 1 . .
C C9 0.4632(2) 0.6571(5) 0.7445(4) 0.0527(9) Uani d . 1 . .
C C10 0.3755(2) 0.6418(5) 0.7208(4) 0.0539(10) Uani d . 1 . .
C C11 0.3384(2) 0.5638(5) 0.8036(4) 0.0561(10) Uani d . 1 . .
C C12 0.2570(3) 0.5556(6) 0.7844(5) 0.0755(13) Uani d . 1 . .
H H12A 0.2327 0.5031 0.8410 0.091 Uiso calc R 1 . .
C C13 0.2120(3) 0.6263(7) 0.6803(5) 0.0842(15) Uani d . 1 . .
H H13A 0.1572 0.6227 0.6672 0.101 Uiso calc R 1 . .
C C14 0.2478(3) 0.7012(7) 0.5968(5) 0.0842(15) Uani d . 1 . .
H H14A 0.2172 0.7477 0.5267 0.101 Uiso calc R 1 . .
C C15 0.3293(3) 0.7087(6) 0.6157(4) 0.0687(12) Uani d . 1 . .
H H15A 0.3532 0.7588 0.5576 0.082 Uiso calc R 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'
Cl Cl 0.1484 0.1585 '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
C1 O1 C2 117.4(5)
C8 N1 C5 126.0(4)
C8 N1 H1A 117.0
C5 N1 H1A 117.0
C9 N2 C8 129.5(3)
C9 N2 H2A 115.3
C8 N2 H2A 115.3
F3 C1 F2' 115.9(9)
F3 C1 F1 101.2(9)
F2' C1 F1 64.4(8)
F3 C1 F1' 79.7(8)
F2' C1 F1' 107.4(11)
F1 C1 F1' 43.2(6)
F3 C1 O1 120.6(9)
F2' C1 O1 119.2(7)
F1 C1 O1 121.0(7)
F1' C1 O1 102.8(8)
F3 C1 F2 106.3(8)
F2' C1 F2 38.4(6)
F1 C1 F2 102.6(9)
F1' C1 F2 145.0(11)
O1 C1 F2 103.1(8)
F3 C1 F3' 32.4(5)
F2' C1 F3' 118.7(9)
F1 C1 F3' 132.9(8)
F1' C1 F3' 108.3(8)
O1 C1 F3' 98.9(8)
F2 C1 F3' 90.4(7)
C7 C2 C3 122.6(4)
C7 C2 O1 118.5(5)
C3 C2 O1 118.8(5)
C2 C3 C4 118.8(4)
C2 C3 H3A 120.6
C4 C3 H3A 120.6
C5 C4 C3 119.0(5)
C5 C4 H4A 120.5
C3 C4 H4A 120.5
C6 C5 C4 120.8(4)
C6 C5 N1 123.9(4)
C4 C5 N1 115.2(4)
C5 C6 C7 118.6(4)
C5 C6 H6A 120.7
C7 C6 H6A 120.7
C2 C7 C6 120.2(5)
C2 C7 H7A 119.9
C6 C7 H7A 119.9
O2 C8 N1 125.6(4)
O2 C8 N2 120.2(3)
N1 C8 N2 114.2(4)
O3 C9 N2 123.4(4)
O3 C9 C10 120.9(4)
N2 C9 C10 115.7(3)
C11 C10 C15 118.6(4)
C11 C10 C9 121.1(3)
C15 C10 C9 120.4(4)
C12 C11 C10 121.1(4)
C12 C11 Cl 118.5(4)
C10 C11 Cl 120.4(3)
C11 C12 C13 119.4(5)
C11 C12 H12A 120.3
C13 C12 H12A 120.3
C14 C13 C12 120.2(5)
C14 C13 H13A 119.9
C12 C13 H13A 119.9
C13 C14 C15 120.5(5)
C13 C14 H14A 119.7
C15 C14 H14A 119.7
C14 C15 C10 120.3(5)
C14 C15 H15A 119.9
C10 C15 H15A 119.9
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Cl C11 1.743(4)
F1 C1 1.324(12)
F2 C1 1.431(11)
F3 C1 1.181(10)
F1' C1 1.327(12)
F2' C1 1.244(11)
F3' C1 1.447(10)
O1 C1 1.334(9)
O1 C2 1.432(5)
O2 C8 1.205(4)
O3 C9 1.233(4)
N1 C8 1.360(5)
N1 C5 1.416(5)
N1 H1A 0.8600
N2 C9 1.361(5)
N2 C8 1.398(5)
N2 H2A 0.8600
C2 C7 1.350(7)
C2 C3 1.354(7)
C3 C4 1.397(6)
C3 H3A 0.9300
C4 C5 1.394(6)
C4 H4A 0.9300
C5 C6 1.379(6)
C6 C7 1.389(6)
C6 H6A 0.9300
C7 H7A 0.9300
C9 C10 1.490(5)
C10 C11 1.382(6)
C10 C15 1.386(5)
C11 C12 1.381(6)
C12 C13 1.383(7)
C12 H12A 0.9300
C13 C14 1.362(7)
C13 H13A 0.9300
C14 C15 1.384(6)
C14 H14A 0.9300
C15 H15A 0.9300
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
N1 H1A O3 . 0.8600 1.9500 2.653(4) 138.00 yes
N2 H2A O2 3_666 0.8600 2.0000 2.851(4) 172.00 yes
C6 H6A O2 . 0.9300 2.2400 2.838(5) 121.00 yes
