#------------------------------------------------------------------------------
#$Date: 2017-10-13 12:31:46 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201979 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/23/11/2231161.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_2231161
loop_
_publ_author_name
'Choi, Hyeong'
'Shim, Yong Suk'
'Han, Byung Hee'
'Kang, Sung Kwon'
'Sung, Chang Keun'
_publ_section_title
;
 1-[3-(Hydroxymethyl)phenyl]-3-phenylurea
;
_journal_coeditor_code           IM2305
_journal_issue                   8
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2094
_journal_paper_doi               10.1107/S1600536811028315
_journal_volume                  67
_journal_year                    2011
_chemical_formula_iupac          'C14 H14 N2 O2'
_chemical_formula_moiety         'C14 H14 N2 O2'
_chemical_formula_sum            'C14 H14 N2 O2'
_chemical_formula_weight         242.27
_chemical_name_systematic
;
1-[3-(Hydroxymethyl)phenyl]-3-phenylurea
;
_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'
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                90
_cell_angle_beta                 109.818(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   14.6207(8)
_cell_length_b                   7.0692(4)
_cell_length_c                   12.4019(5)
_cell_measurement_reflns_used    2624
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      27.98
_cell_measurement_theta_min      3.24
_cell_volume                     1205.90(11)
_computing_cell_refinement       'SAINT (Bruker, 2002)'
_computing_data_collection       'SMART (Bruker, 2002)'
_computing_data_reduction        'SAINT (Bruker, 2002)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.972
_diffrn_measured_fraction_theta_max 0.972
_diffrn_measurement_device_type  'Bruker SMART CCD area-detector'
_diffrn_measurement_method       'φ and ω'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0515
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            9960
_diffrn_reflns_theta_full        27.5
_diffrn_reflns_theta_max         27.5
_diffrn_reflns_theta_min         2.96
_exptl_absorpt_coefficient_mu    0.091
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.334
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             512
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.142
_refine_diff_density_min         -0.208
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.929
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     175
_refine_ls_number_reflns         2694
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.929
_refine_ls_R_factor_gt           0.0409
_refine_ls_shift/su_max          0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0584P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.1106
_reflns_number_gt                1664
_reflns_number_total             2694
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            im2305.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2231161
_cod_database_fobs_code          2231161
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
C C1 0.13667(11) 0.36148(19) 0.11590(11) 0.0385(3) Uani d . 1
C C2 0.07277(11) 0.2820(2) 0.01677(13) 0.0471(4) Uani d . 1
H H2 0.0933 0.2595 -0.0453 0.057 Uiso calc R 1
C C3 -0.02094(12) 0.2359(2) 0.00922(14) 0.0546(4) Uani d . 1
H H3 -0.0632 0.1839 -0.0581 0.066 Uiso calc R 1
C C4 -0.05198(12) 0.2664(2) 0.10023(15) 0.0581(5) Uani d . 1
H H4 -0.1149 0.2343 0.0955 0.07 Uiso calc R 1
C C5 0.01144(13) 0.3456(3) 0.19916(15) 0.0619(5) Uani d . 1
H H5 -0.0093 0.3672 0.2611 0.074 Uiso calc R 1
C C6 0.10517(12) 0.3932(2) 0.20757(12) 0.0524(4) Uani d . 1
H H6 0.147 0.4464 0.2748 0.063 Uiso calc R 1
N N7 0.22912(9) 0.41144(18) 0.11382(11) 0.0442(3) Uani d . 1
H H7 0.2359(11) 0.410(2) 0.0471(14) 0.049(4) Uiso d . 1
C C8 0.31390(11) 0.42001(18) 0.20514(11) 0.0381(3) Uani d . 1
O O9 0.31723(8) 0.41011(14) 0.30535(8) 0.0495(3) Uani d . 1
N N10 0.39322(9) 0.44032(17) 0.17245(10) 0.0436(3) Uani d . 1
H H10 0.3815(11) 0.444(2) 0.0964(15) 0.057(5) Uiso d . 1
C C11 0.49231(11) 0.43970(18) 0.24098(11) 0.0369(3) Uani d . 1
C C12 0.52658(11) 0.44241(19) 0.35949(12) 0.0454(4) Uani d . 1
H H12 0.4834 0.4428 0.3999 0.055 Uiso calc R 1
C C13 0.62598(12) 0.4446(2) 0.41732(13) 0.0516(4) Uani d . 1
H H13 0.6491 0.4462 0.497 0.062 Uiso calc R 1
C C14 0.69114(12) 0.4444(2) 0.35936(13) 0.0481(4) Uani d . 1
H H14 0.7576 0.4466 0.3997 0.058 Uiso calc R 1
C C15 0.65760(11) 0.44079(19) 0.24059(12) 0.0426(4) Uani d . 1
C C16 0.55875(11) 0.43755(19) 0.18285(12) 0.0423(4) Uani d . 1
H H16 0.5359 0.4338 0.1032 0.051 Uiso calc R 1
C C17 0.72705(12) 0.4432(2) 0.17456(14) 0.0554(4) Uani d . 1
H H17A 0.7921 0.4684 0.2272 0.066 Uiso calc R 1
H H17B 0.7276 0.319 0.1415 0.066 Uiso calc R 1
O O18 0.70325(8) 0.58030(19) 0.08550(9) 0.0559(3) Uani d . 1
H H18 0.6949(15) 0.685(3) 0.1155(18) 0.094(8) Uiso d . 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 0 '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 0.006 '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
C6 C1 C2 118.88(14)
C6 C1 N7 124.41(14)
C2 C1 N7 116.66(12)
C3 C2 C1 120.73(14)
C3 C2 H2 119.6
C1 C2 H2 119.6
C4 C3 C2 120.39(16)
C4 C3 H3 119.8
C2 C3 H3 119.8
C3 C4 C5 119.08(15)
C3 C4 H4 120.5
C5 C4 H4 120.5
C6 C5 C4 121.08(15)
C6 C5 H5 119.5
C4 C5 H5 119.5
C5 C6 C1 119.84(15)
C5 C6 H6 120.1
C1 C6 H6 120.1
C8 N7 C1 127.08(12)
C8 N7 H7 115.2(10)
C1 N7 H7 116.0(10)
O9 C8 N10 124.20(14)
O9 C8 N7 123.29(13)
N10 C8 N7 112.51(12)
C8 N10 C11 128.77(12)
C8 N10 H10 115.9(10)
C11 N10 H10 115.1(10)
C12 C11 C16 119.05(14)
C12 C11 N10 124.67(13)
C16 C11 N10 116.28(12)
C11 C12 C13 119.26(14)
C11 C12 H12 120.4
C13 C12 H12 120.4
C14 C13 C12 121.38(14)
C14 C13 H13 119.3
C12 C13 H13 119.3
C13 C14 C15 119.84(15)
C13 C14 H14 120.1
C15 C14 H14 120.1
C16 C15 C14 118.90(14)
C16 C15 C17 119.96(13)
C14 C15 C17 121.13(14)
C15 C16 C11 121.56(13)
C15 C16 H16 119.2
C11 C16 H16 119.2
O18 C17 C15 113.44(13)
O18 C17 H17A 108.9
C15 C17 H17A 108.9
O18 C17 H17B 108.9
C15 C17 H17B 108.9
H17A C17 H17B 107.7
C17 O18 H18 106.6(14)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 C6 1.3820(19)
C1 C2 1.386(2)
C1 N7 1.4058(19)
C2 C3 1.380(2)
C2 H2 0.93
C3 C4 1.369(2)
C3 H3 0.93
C4 C5 1.381(2)
C4 H4 0.93
C5 C6 1.380(2)
C5 H5 0.93
C6 H6 0.93
N7 C8 1.3678(19)
N7 H7 0.866(17)
C8 O9 1.2291(15)
C8 N10 1.3597(18)
N10 C11 1.4094(18)
N10 H10 0.900(17)
C11 C12 1.3829(19)
C11 C16 1.392(2)
C12 C13 1.386(2)
C12 H12 0.93
C13 C14 1.374(2)
C13 H13 0.93
C14 C15 1.386(2)
C14 H14 0.93
C15 C16 1.379(2)
C15 C17 1.505(2)
C16 H16 0.93
C17 O18 1.421(2)
C17 H17A 0.97
C17 H17B 0.97
O18 H18 0.86(2)
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
N7 H7 O18 3_665 0.87(2) 2.12(2) 2.958(2) 163.0(10)
N10 H10 O18 3_665 0.90(2) 2.18(2) 3.031(2) 157.0(10)
O18 H18 O9 2_655 0.86(2) 1.91(2) 2.763(2) 175(2)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 26455105
