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#$Date: 2015-06-01 12:12:48 +0300 (Mon, 01 Jun 2015) $
#$Revision: 137625 $
#$URL: svn://www.crystallography.net/cod/cif/1/52/01/1520178.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_1520178
loop_
_publ_author_name
'Huth, Susanne L.'
'Threlfall, Terry L.'
'Hursthouse, Michael B.'
_publ_section_title
;
 N,N'-bis-Phenylurea
;
_journal_name_full               'Crystal Structure Report Archive'
_journal_page_first              681
_journal_year                    2008
_chemical_formula_sum            'C13 H12 N2 O'
_chemical_formula_weight         212.25
_chemical_name_systematic
;
 N,N'-bis-Phenylurea
;
_space_group_IT_number           33
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2c -2n'
_symmetry_space_group_name_H-M   'P n a 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.0662(3)
_cell_length_b                   10.3420(4)
_cell_length_c                   11.7380(4)
_cell_measurement_reflns_used    7942
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      27.48
_cell_measurement_theta_min      2.91
_cell_volume                     1100.59(7)
_computing_cell_refinement
'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)'
_computing_data_collection       'COLLECT (Hooft, R.W.W., 1998)'
_computing_data_reduction
'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      120(2)
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type
'Bruker-Nonius APEX II CCD camera on κ-goniostat'
_diffrn_measurement_method       'φ & ω scans'
_diffrn_radiation_monochromator  '10cm confocal mirrors'
_diffrn_radiation_source         'Bruker-Nonius FR591 rotating anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0530
_diffrn_reflns_av_sigmaI/netI    0.0550
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            9386
_diffrn_reflns_theta_full        27.49
_diffrn_reflns_theta_max         27.49
_diffrn_reflns_theta_min         2.99
_exptl_absorpt_coefficient_mu    0.083
_exptl_absorpt_correction_T_max  0.9983
_exptl_absorpt_correction_T_min  0.9612
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS 2007/2 (Sheldrick, G.M., 2007)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.281
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       'cut needle'
_exptl_crystal_F_000             448
_exptl_crystal_size_max          0.48
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.199
_refine_diff_density_min         -0.202
_refine_diff_density_rms         0.048
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -1(2)
_refine_ls_extinction_coef       0.010(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.080
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     154
_refine_ls_number_reflns         2433
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.079
_refine_ls_R_factor_all          0.0691
_refine_ls_R_factor_gt           0.0500
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0254P)²+0.5368P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0976
_refine_ls_wR_factor_ref         0.1075
_reflns_number_gt                1999
_reflns_number_total             2433
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            eCrystal-681.cif
_cod_data_source_block           2008lsh045
_cod_depositor_comments
;
Citation :
Huth, Susanne L. and Threlfall, Terry L. and Hursthouse, Michael B. (2008) 
University of Southampton, Crystal Structure Report Archive. 
(doi:10.5258/ecrystals/681)

More at:
http://ecrystals.chem.soton.ac.uk/681/

The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Orthorhombic' changed to
'orthorhombic' according to the built-in table from CIF Core
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 3392 2015-05-12 13:50:21Z andrius 
;
_cod_database_code               1520178
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'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C -0.0321(2) 0.6748(2) 0.9062(2) 0.0259(5) Uani 1 1 d . . .
C2 C 0.0757(3) 0.7465(2) 0.9633(2) 0.0286(5) Uani 1 1 d . . .
H2 H 0.1141 0.8235 0.9307 0.034 Uiso 1 1 calc R . .
C3 C 0.1259(3) 0.7034(3) 1.0682(2) 0.0351(6) Uani 1 1 d . . .
H3 H 0.2012 0.7502 1.1065 0.042 Uiso 1 1 calc R . .
C4 C 0.0677(3) 0.5934(3) 1.1180(3) 0.0416(7) Uani 1 1 d . . .
H4 H 0.1016 0.5656 1.1906 0.050 Uiso 1 1 calc R . .
C5 C -0.0403(3) 0.5243(3) 1.0611(2) 0.0413(7) Uani 1 1 d . . .
H5 H -0.0810 0.4488 1.0950 0.050 Uiso 1 1 calc R . .
C6 C -0.0894(3) 0.5643(2) 0.9552(2) 0.0319(6) Uani 1 1 d . . .
H6 H -0.1625 0.5158 0.9162 0.038 Uiso 1 1 calc R . .
C7 C -0.0115(2) 0.7658(2) 0.7127(2) 0.0229(5) Uani 1 1 d . . .
C8 C -0.0364(3) 0.8451(2) 0.5160(2) 0.0251(5) Uani 1 1 d . . .
C9 C 0.0837(2) 0.9287(2) 0.5108(2) 0.0272(5) Uani 1 1 d . . .
H9 H 0.1296 0.9574 0.5790 0.033 Uiso 1 1 calc R . .
C10 C 0.1362(3) 0.9700(2) 0.4062(2) 0.0322(5) Uani 1 1 d . . .
H10 H 0.2196 1.0255 0.4032 0.039 Uiso 1 1 calc R . .
C11 C 0.0686(3) 0.9313(3) 0.3058(2) 0.0335(6) Uani 1 1 d . . .
H11 H 0.1057 0.9589 0.2341 0.040 Uiso 1 1 calc R . .
C12 C -0.0536(3) 0.8520(3) 0.3117(2) 0.0366(6) Uani 1 1 d . . .
H12 H -0.1026 0.8272 0.2436 0.044 Uiso 1 1 calc R . .
C13 C -0.1056(3) 0.8082(2) 0.4153(2) 0.0317(5) Uani 1 1 d . . .
H13 H -0.1890 0.7527 0.4178 0.038 Uiso 1 1 calc R . .
N1 N -0.0909(2) 0.7171(2) 0.80033(16) 0.0248(5) Uani 1 1 d D . .
N2 N -0.0941(2) 0.7997(2) 0.62005(18) 0.0262(5) Uani 1 1 d D . .
O1 O 0.12384(15) 0.77817(17) 0.71479(16) 0.0298(4) Uani 1 1 d . . .
H1N H -0.1852(19) 0.708(3) 0.791(2) 0.040(8) Uiso 1 1 d D . .
H2N H -0.185(2) 0.772(2) 0.620(2) 0.027(7) Uiso 1 1 d D . .
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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
C6 C1 C2 120.1(2) . .
C6 C1 N1 118.5(2) . .
C2 C1 N1 121.3(2) . .
C3 C2 C1 119.0(2) . .
C3 C2 H2 120.5 . .
C1 C2 H2 120.5 . .
C4 C3 C2 121.0(3) . .
C4 C3 H3 119.5 . .
C2 C3 H3 119.5 . .
C3 C4 C5 119.4(3) . .
C3 C4 H4 120.3 . .
C5 C4 H4 120.3 . .
C6 C5 C4 120.4(3) . .
C6 C5 H5 119.8 . .
C4 C5 H5 119.8 . .
C1 C6 C5 120.1(2) . .
C1 C6 H6 119.9 . .
C5 C6 H6 119.9 . .
O1 C7 N1 123.5(2) . .
O1 C7 N2 122.3(2) . .
N1 C7 N2 114.12(17) . .
C9 C8 C13 119.1(2) . .
C9 C8 N2 122.4(2) . .
C13 C8 N2 118.5(2) . .
C10 C9 C8 120.0(2) . .
C10 C9 H9 120.0 . .
C8 C9 H9 120.0 . .
C9 C10 C11 120.8(2) . .
C9 C10 H10 119.6 . .
C11 C10 H10 119.6 . .
C12 C11 C10 118.9(2) . .
C12 C11 H11 120.6 . .
C10 C11 H11 120.6 . .
C11 C12 C13 120.9(2) . .
C11 C12 H12 119.5 . .
C13 C12 H12 119.5 . .
C12 C13 C8 120.3(2) . .
C12 C13 H13 119.9 . .
C8 C13 H13 119.9 . .
C7 N1 C1 125.42(19) . .
C7 N1 H1N 117.9(19) . .
C1 N1 H1N 116.6(19) . .
C7 N2 C8 124.85(19) . .
C7 N2 H2N 115.7(18) . .
C8 N2 H2N 117.4(18) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 C6 1.381(3) .
C1 C2 1.398(4) .
C1 N1 1.421(3) .
C2 C3 1.386(4) .
C2 H2 0.9500 .
C3 C4 1.383(4) .
C3 H3 0.9500 .
C4 C5 1.385(4) .
C4 H4 0.9500 .
C5 C6 1.384(4) .
C5 H5 0.9500 .
C6 H6 0.9500 .
C7 O1 1.234(2) .
C7 N1 1.353(3) .
C7 N2 1.366(3) .
C8 C9 1.392(3) .
C8 C13 1.392(4) .
C8 N2 1.409(3) .
C9 C10 1.384(4) .
C9 H9 0.9500 .
C10 C11 1.388(4) .
C10 H10 0.9500 .
C11 C12 1.380(4) .
C11 H11 0.9500 .
C12 C13 1.381(4) .
C12 H12 0.9500 .
C13 H13 0.9500 .
N1 H1N 0.868(17) .
N2 H2N 0.868(17) .
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H1N O1 0.868(17) 1.953(19) 2.775(2) 157(3) 3_465
N2 H2N O1 0.868(17) 2.13(2) 2.902(3) 148(2) 3_465
