#------------------------------------------------------------------------------
#$Date: 2016-02-20 18:35:30 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176787 $
#$URL: svn://www.crystallography.net/cod/cif/2/21/86/2218627.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_2218627
loop_
_publ_author_name
'Yu, Da-sheng'
'Li, Fang-shi'
'Yao, Wei'
'Liu, Yin-hong'
'Lu, Chui'
_publ_section_title
;
 N,N-Dimethyl-N'-[3-(trifluoromethyl)phenyl]urea
;
_journal_coeditor_code           BX2148
_journal_issue                   7
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1220
_journal_paper_doi               10.1107/S1600536808016656
_journal_volume                  64
_journal_year                    2008
_chemical_formula_iupac          'C10 H11 F3 N2 O'
_chemical_formula_moiety         'C10 H11 F3 N2 O'
_chemical_formula_sum            'C10 H11 F3 N2 O'
_chemical_formula_weight         232.20
_chemical_name_common            Fluometuron
_chemical_name_systematic
;
N,N-Dimethyl-N'-[3-(trifluoromethyl)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
_audit_creation_method           SHELXL97
_cell_angle_alpha                90.00
_cell_angle_beta                 96.89(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   11.005(2)
_cell_length_b                   9.991(2)
_cell_length_c                   10.012(2)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      13
_cell_measurement_theta_min      10
_cell_volume                     1092.9(4)
_computing_cell_refinement       'CAD4 Software (Enraf--Nonius, 1989)'
_computing_data_collection       'CAD4 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 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Enraf--Nonius CAD4'
_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  0.0204
_diffrn_reflns_av_sigmaI/netI    0.0344
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       0
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            2076
_diffrn_reflns_theta_full        25.15
_diffrn_reflns_theta_max         25.15
_diffrn_reflns_theta_min         1.86
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 200
_diffrn_standards_interval_time  2
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.127
_exptl_absorpt_correction_T_max  0.9874
_exptl_absorpt_correction_T_min  0.9628
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(North et al., 1968)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.411
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             480
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.185
_refine_diff_density_min         -0.148
_refine_ls_extinction_coef       0.162(9)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL97 (Sheldrick, 2008)'
_refine_ls_goodness_of_fit_ref   1.003
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     169
_refine_ls_number_reflns         1953
_refine_ls_number_restraints     36
_refine_ls_restrained_S_all      1.102
_refine_ls_R_factor_all          0.0834
_refine_ls_R_factor_gt           0.0530
_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)+(0.0500P)²+0.6300P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1159
_refine_ls_wR_factor_ref         0.1369
_reflns_number_gt                1335
_reflns_number_total             1953
_reflns_threshold_expression     I>2\si(I)
_cod_data_source_file            bx2148.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2218627
_cod_database_fobs_code          2218627
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
C C1 -0.4416(3) 0.3310(5) 0.7481(4) 0.083 Uani d . 1 . .
F F1 -0.4245(19) 0.355(3) 0.6336(15) 0.097(6) Uani d PU 0.176(9) A 1
F F2 -0.444(2) 0.1924(18) 0.754(3) 0.127(8) Uani d PU 0.176(9) A 1
F F3 -0.5413(13) 0.368(3) 0.773(2) 0.102(6) Uani d PU 0.176(9) A 1
F F1' -0.4988(5) 0.4328(5) 0.6794(6) 0.149(2) Uani d PU 0.824(9) A 2
F F2' -0.4081(3) 0.2491(7) 0.6573(5) 0.126(2) Uani d PU 0.824(9) A 2
F F3' -0.5304(4) 0.2692(7) 0.8022(4) 0.1244(19) Uani d PU 0.824(9) A 2
O O -0.00769(19) 0.2044(2) 0.79738(17) 0.0702(7) Uani d . 1 . .
N N1 -0.0375(2) 0.2618(2) 1.0096(2) 0.0532(7) Uani d . 1 . .
H H1A -0.0106 0.2548 1.0935 0.064 Uiso calc R 1 . .
N N2 0.1237(2) 0.1254(3) 0.9701(2) 0.0569(7) Uani d . 1 . .
C C2 -0.3406(3) 0.3766(3) 0.8510(3) 0.0553(8) Uani d . 1 A .
C C3 -0.2362(2) 0.2993(3) 0.8761(3) 0.0508(7) Uani d . 1 . .
H H3A -0.2280 0.2211 0.8277 0.061 Uiso calc R 1 A .
C C4 -0.1437(2) 0.3397(3) 0.9745(2) 0.0460(7) Uani d . 1 A .
C C5 -0.1575(3) 0.4563(3) 1.0448(3) 0.0572(8) Uani d . 1 . .
H H5A -0.0954 0.4840 1.1102 0.069 Uiso calc R 1 A .
C C6 -0.2618(3) 0.5322(3) 1.0194(3) 0.0649(9) Uani d . 1 A .
H H6A -0.2703 0.6103 1.0680 0.078 Uiso calc R 1 . .
C C7 -0.3543(3) 0.4927(3) 0.9216(3) 0.0627(9) Uani d . 1 . .
H H7A -0.4249 0.5439 0.9037 0.075 Uiso calc R 1 A .
C C8 0.0253(2) 0.1970(3) 0.9195(2) 0.0492(7) Uani d . 1 . .
C C9 0.1950(3) 0.0560(4) 0.8790(3) 0.0814(11) Uani d . 1 . .
H H9A 0.1592 0.0706 0.7879 0.122 Uiso calc R 1 . .
H H9B 0.1957 -0.0381 0.8983 0.122 Uiso calc R 1 . .
H H9C 0.2773 0.0896 0.8903 0.122 Uiso calc R 1 . .
C C10 0.1652(3) 0.1137(4) 1.1124(3) 0.0765(11) Uani d . 1 . .
H H10A 0.0972 0.0913 1.1599 0.115 Uiso calc R 1 . .
H H10B 0.1997 0.1974 1.1454 0.115 Uiso calc R 1 . .
H H10C 0.2262 0.0448 1.1264 0.115 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'
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
F1 C1 F3 112.7(14) no
F1 C1 F2' 51.4(11) ?
F3 C1 F2' 132.5(9) ?
F1 C1 F3' 133.4(8) ?
F3 C1 F3' 47.9(13) ?
F2' C1 F3' 106.1(5) no
F1 C1 F1' 58.6(12) ?
F3 C1 F1' 59.6(12) ?
F2' C1 F1' 105.8(5) no
F3' C1 F1' 103.9(4) no
F1 C1 F2 104.2(15) no
F3 C1 F2 106.2(16) no
F2' C1 F2 54.1(12) ?
F3' C1 F2 60.0(12) ?
F1' C1 F2 140.5(8) ?
F1 C1 C2 113.9(8) no
F3 C1 C2 112.2(9) no
F2' C1 C2 114.9(3) no
F3' C1 C2 112.6(4) no
F1' C1 C2 112.7(4) no
F2 C1 C2 106.8(8) no
C8 N1 C4 124.5(2) no
C8 N1 H1A 117.7 ?
C4 N1 H1A 117.7 ?
C8 N2 C10 123.9(2) no
C8 N2 C9 119.3(2) no
C10 N2 C9 116.8(3) no
C7 C2 C3 121.2(3) ?
C7 C2 C1 119.6(3) ?
C3 C2 C1 119.3(3) ?
C2 C3 C4 119.3(3) ?
C2 C3 H3A 120.3 ?
C4 C3 H3A 120.3 ?
C5 C4 C3 119.4(3) ?
C5 C4 N1 118.5(2) no
C3 C4 N1 122.1(2) no
C6 C5 C4 120.8(3) ?
C6 C5 H5A 119.6 ?
C4 C5 H5A 119.6 ?
C5 C6 C7 120.1(3) ?
C5 C6 H6A 120.0 ?
C7 C6 H6A 120.0 ?
C2 C7 C6 119.2(3) ?
C2 C7 H7A 120.4 ?
C6 C7 H7A 120.4 ?
O C8 N2 122.2(3) no
O C8 N1 120.9(3) no
N2 C8 N1 116.9(2) no
N2 C9 H9A 109.5 ?
N2 C9 H9B 109.5 ?
H9A C9 H9B 109.5 ?
N2 C9 H9C 109.5 ?
H9A C9 H9C 109.5 ?
H9B C9 H9C 109.5 ?
N2 C10 H10A 109.5 ?
N2 C10 H10B 109.5 ?
H10A C10 H10B 109.5 ?
N2 C10 H10C 109.5 ?
H10A C10 H10C 109.5 ?
H10B C10 H10C 109.5 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
C1 F1 1.208(16) no
C1 F3 1.214(15) no
C1 F2' 1.308(5) no
C1 F3' 1.325(6) no
C1 F1' 1.341(6) no
C1 F2 1.386(18) no
C1 C2 1.494(5) ?
O C8 1.235(3) no
N1 C8 1.364(3) no
N1 C4 1.412(3) no
N1 H1A 0.8600 ?
N2 C8 1.345(3) no
N2 C10 1.448(4) no
N2 C9 1.449(4) no
C2 C7 1.376(4) ?
C2 C3 1.382(4) ?
C3 C4 1.389(4) ?
C3 H3A 0.9300 ?
C4 C5 1.380(4) ?
C5 C6 1.374(4) ?
C5 H5A 0.9300 ?
C6 C7 1.383(4) ?
C6 H6A 0.9300 ?
C7 H7A 0.9300 ?
C9 H9A 0.9600 ?
C9 H9B 0.9600 ?
C9 H9C 0.9600 ?
C10 H10A 0.9600 ?
C10 H10B 0.9600 ?
C10 H10C 0.9600 ?
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 O 4_566 0.8600 2.0800 2.880(3) 155.00 yes
C3 H3A O . 0.9300 2.4800 2.884(3) 106.00 yes
C9 H9A O . 0.9600 2.2800 2.721(4) 107.00 yes
