#------------------------------------------------------------------------------
#$Date: 2017-10-13 12:31:46 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201979 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/23/43/2234329.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_2234329
loop_
_publ_author_name
'Li, Yu-Feng'
'Jiang, Jin-He'
_publ_section_title
;
 1-(4-Chlorophenyl)-3-(morpholin-4-yl)urea
;
_journal_coeditor_code           LH5438
_journal_issue                   4
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1219
_journal_paper_doi               10.1107/S1600536812012615
_journal_volume                  68
_journal_year                    2012
_chemical_formula_iupac          'C11 H14 Cl N3 O2'
_chemical_formula_moiety         'C11 H14 Cl N3 O2'
_chemical_formula_sum            'C11 H14 Cl N3 O2'
_chemical_formula_weight         255.70
_chemical_name_systematic
;
1-(4-Chlorophenyl)-3-(morpholin-4-yl)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           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 94.03(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   13.684(3)
_cell_length_b                   9.3612(19)
_cell_length_c                   9.758(2)
_cell_measurement_reflns_used    1502
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.48
_cell_measurement_theta_min      3.01
_cell_volume                     1246.9(5)
_computing_cell_refinement       'SAINT (Bruker 1997)'
_computing_data_collection       'SMART (Bruker 1997)'
_computing_data_reduction        'SAINT (Bruker 1997)'
_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      293(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker SMART CCD'
_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  0.0429
_diffrn_reflns_av_sigmaI/netI    0.0388
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            11894
_diffrn_reflns_theta_full        27.48
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_min         3.02
_exptl_absorpt_coefficient_mu    0.301
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.362
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             536
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.19
_refine_diff_density_max         0.199
_refine_diff_density_min         -0.287
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.172
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     154
_refine_ls_number_reflns         2857
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.172
_refine_ls_R_factor_all          0.0990
_refine_ls_R_factor_gt           0.0448
_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)+(0.0850P)²+0.0207P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1251
_refine_ls_wR_factor_ref         0.1801
_reflns_number_gt                1502
_reflns_number_total             2857
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            lh5438.cif
_cod_data_source_block           I
_cod_original_cell_volume        1246.8(4)
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2234329
_cod_database_fobs_code          2234329
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_symmetry_multiplicity
Cl Cl1 0.92775(5) 0.08842(12) 0.30739(8) 0.0988(4) Uani d . 1 1
O O2 1.39233(12) 0.0438(2) 0.09026(16) 0.0612(5) Uani d . 1 1
C C6 1.18312(16) 0.0784(3) 0.0412(2) 0.0493(6) Uani d . 1 1
N N3 1.25450(14) 0.0646(2) -0.0549(2) 0.0561(5) Uani d . 1 1
H H3A 1.2345 0.0708 -0.1403 0.067 Uiso calc R 1 1
N N1 1.35490(13) 0.0024(2) -0.26930(19) 0.0535(5) Uani d . 1 1
O O1 1.35069(15) -0.0687(2) -0.55127(17) 0.0697(5) Uani d . 1 1
N N2 1.40369(14) 0.0221(3) -0.1380(2) 0.0656(6) Uani d . 1 1
H H2A 1.4667 0.0212 -0.1292 0.079 Uiso calc R 1 1
C C5 1.35207(17) 0.0425(3) -0.0260(2) 0.0504(6) Uani d . 1 1
C C8 1.1131(2) 0.0212(3) 0.2519(3) 0.0674(7) Uani d . 1 1
H H8A 1.1185 -0.0217 0.3381 0.081 Uiso calc R 1 1
C C11 1.09794(16) 0.1525(3) -0.0004(3) 0.0592(6) Uani d . 1 1
H H11A 1.0931 0.1986 -0.0850 0.071 Uiso calc R 1 1
C C9 1.02870(18) 0.0905(3) 0.2072(3) 0.0644(7) Uani d . 1 1
C C10 1.02095(18) 0.1582(3) 0.0826(3) 0.0672(7) Uani d . 1 1
H H10A 0.9641 0.2076 0.0543 0.081 Uiso calc R 1 1
C C7 1.19009(18) 0.0152(3) 0.1684(2) 0.0608(7) Uani d . 1 1
H H7A 1.2474 -0.0321 0.1986 0.073 Uiso calc R 1 1
C C3 1.3409(2) 0.0735(3) -0.5071(3) 0.0734(8) Uani d . 1 1
H H3B 1.2720 0.0954 -0.5020 0.088 Uiso calc R 1 1
H H3C 1.3669 0.1373 -0.5739 0.088 Uiso calc R 1 1
C C4 1.3938(2) 0.0989(3) -0.3690(3) 0.0666(7) Uani d . 1 1
H H4A 1.4634 0.0822 -0.3741 0.080 Uiso calc R 1 1
H H4B 1.3847 0.1972 -0.3409 0.080 Uiso calc R 1 1
C C2 1.3146(2) -0.1633(3) -0.4542(2) 0.0763(8) Uani d . 1 1
H H2B 1.3226 -0.2609 -0.4849 0.092 Uiso calc R 1 1
H H2C 1.2451 -0.1462 -0.4478 0.092 Uiso calc R 1 1
C C1 1.3671(2) -0.1449(3) -0.3145(3) 0.0709(8) Uani d . 1 1
H H1A 1.3404 -0.2101 -0.2496 0.085 Uiso calc R 1 1
H H1B 1.4362 -0.1662 -0.3191 0.085 Uiso calc R 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'
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
C7 C6 C11 118.8(2)
C7 C6 N3 123.8(2)
C11 C6 N3 117.3(2)
C5 N3 C6 126.35(19)
C5 N3 H3A 116.8
C6 N3 H3A 116.8
N2 N1 C4 110.6(2)
N2 N1 C1 109.9(2)
C4 N1 C1 109.2(2)
C3 O1 C2 110.0(2)
C5 N2 N1 120.60(19)
C5 N2 H2A 119.7
N1 N2 H2A 119.7
O2 C5 N2 121.4(2)
O2 C5 N3 124.1(2)
N2 C5 N3 114.4(2)
C9 C8 C7 119.6(3)
C9 C8 H8A 120.2
C7 C8 H8A 120.2
C10 C11 C6 120.6(2)
C10 C11 H11A 119.7
C6 C11 H11A 119.7
C8 C9 C10 120.9(2)
C8 C9 Cl1 119.9(2)
C10 C9 Cl1 119.1(2)
C9 C10 C11 119.4(2)
C9 C10 H10A 120.3
C11 C10 H10A 120.3
C6 C7 C8 120.7(2)
C6 C7 H7A 119.7
C8 C7 H7A 119.7
O1 C3 C4 112.0(2)
O1 C3 H3B 109.2
C4 C3 H3B 109.2
O1 C3 H3C 109.2
C4 C3 H3C 109.2
H3B C3 H3C 107.9
N1 C4 C3 109.0(2)
N1 C4 H4A 109.9
C3 C4 H4A 109.9
N1 C4 H4B 109.9
C3 C4 H4B 109.9
H4A C4 H4B 108.3
O1 C2 C1 111.6(2)
O1 C2 H2B 109.3
C1 C2 H2B 109.3
O1 C2 H2C 109.3
C1 C2 H2C 109.3
H2B C2 H2C 108.0
N1 C1 C2 108.9(2)
N1 C1 H1A 109.9
C2 C1 H1A 109.9
N1 C1 H1B 109.9
C2 C1 H1B 109.9
H1A C1 H1B 108.3
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Cl1 C9 1.748(3)
O2 C5 1.226(3)
C6 C7 1.373(3)
C6 C11 1.392(3)
C6 N3 1.407(3)
N3 C5 1.361(3)
N3 H3A 0.8600
N1 N2 1.414(3)
N1 C4 1.456(3)
N1 C1 1.461(3)
O1 C3 1.409(4)
O1 C2 1.411(3)
N2 C5 1.356(3)
N2 H2A 0.8600
C8 C9 1.369(4)
C8 C7 1.377(4)
C8 H8A 0.9300
C11 C10 1.374(3)
C11 H11A 0.9300
C9 C10 1.369(4)
C10 H10A 0.9300
C7 H7A 0.9300
C3 C4 1.503(4)
C3 H3B 0.9700
C3 H3C 0.9700
C4 H4A 0.9700
C4 H4B 0.9700
C2 C1 1.505(4)
C2 H2B 0.9700
C2 H2C 0.9700
C1 H1A 0.9700
C1 H1B 0.9700
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 O2 3_855 0.86 2.03 2.865(3) 162
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 4241712
