#------------------------------------------------------------------------------
#$Date: 2016-02-21 11:56:54 +0200 (Sun, 21 Feb 2016) $
#$Revision: 176809 $
#$URL: svn://www.crystallography.net/cod/cif/2/24/03/2240340.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_2240340
loop_
_publ_author_name
'Jayalakshmi, L.'
'Ramalingan, C.'
'Sridhar, B.'
'Selvanayagam, S.'
_publ_section_title
;
 Crystal structure of 1-(2,4-dimethylphenyl)urea
;
_journal_coeditor_code           SU5043
_journal_issue                   1
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o60
_journal_page_last               o61
_journal_paper_doi               10.1107/S2056989014027431
_journal_volume                  71
_journal_year                    2015
_chemical_formula_iupac          'C9 H12 N2 O'
_chemical_formula_moiety         'C9 H12 N2 O'
_chemical_formula_sum            'C9 H12 N2 O'
_chemical_formula_weight         164.21
_chemical_name_systematic
;
1-(2,4-Dimethylphenyl)urea
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2013
_cell_angle_alpha                90
_cell_angle_beta                 93.530(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   14.631(4)
_cell_length_b                   7.0633(19)
_cell_length_c                   8.786(2)
_cell_measurement_reflns_used    6568
_cell_measurement_temperature    292(2)
_cell_measurement_theta_max      24.6
_cell_measurement_theta_min      2.8
_cell_volume                     906.3(4)
_computing_cell_refinement
;
SAINT (Bruker, 2001)
;
_computing_data_collection
;
SMART (Bruker, 2001)
;
_computing_data_reduction
;
SAINT (Bruker, 2001)
;
_computing_molecular_graphics
;
ORTEP-3 for Windows (Farrugia, 2012) and PLATON (Spek, 2009)
;
_computing_publication_material
;
SHELXL2013 (Sheldrick, 2008) and PLATON (Spek, 2009)
;
_computing_structure_refinement
;
SHELXL2013 (Sheldrick, 2008)
;
_computing_structure_solution
;
SHELXS97 (Sheldrick, 2008)
;
_diffrn_ambient_temperature      292(2)
_diffrn_measured_fraction_theta_full 0.947
_diffrn_measured_fraction_theta_max 0.968
_diffrn_measurement_device_type  'Bruker SMART APEX CCD area-detector'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0277
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            8026
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         24.997
_diffrn_reflns_theta_min         2.790
_exptl_absorpt_coefficient_mu    0.081
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            Colourless
_exptl_crystal_density_diffrn    1.204
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Block
_exptl_crystal_F_000             352
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.16
_refine_diff_density_max         0.868
_refine_diff_density_min         -0.318
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.586
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     119
_refine_ls_number_reflns         1556
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.585
_refine_ls_R_factor_all          0.1095
_refine_ls_R_factor_gt           0.0995
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
 w=1/[σ²(Fo²)+(0.2000P)²]
 where P=(Fo²+2Fc²)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.3206
_refine_ls_wR_factor_ref         0.3486
_reflns_number_gt                1284
_reflns_number_total             1556
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            su5043sup1.cif
_cod_data_source_block           I
_cod_original_cell_volume        906.2(4)
_cod_database_code               2240340
_cod_database_fobs_code          2240340
#BEGIN Tags that were not found in dictionaries:
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelxl_version_number           20.13
#END Tags that were not found in dictionaries
loop_
_space_group_symop_operation_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_occupancy
O O1 0.40043(14) 0.1453(3) 0.55423(18) 0.0634(8) Uani d 1
N N1 0.32526(19) 0.2851(4) 0.3520(3) 0.0709(10) Uani d 1
H H1 0.3186 0.2927 0.2543 0.085 Uiso calc 1
N N2 0.4476(2) 0.0982(4) 0.3174(3) 0.0682(9) Uani d 1
H H2A 0.437(2) 0.125(4) 0.2228(15) 0.060(8) Uiso d 1
H H2B 0.4934(19) 0.036(5) 0.360(4) 0.089(11) Uiso d 1
C C1 0.1253(4) 0.4077(12) 0.5679(5) 0.1144(17) Uani d 1
H H1A 0.0700 0.3530 0.5912 0.137 Uiso calc 1
C C2 0.1467(3) 0.5877(12) 0.6154(4) 0.122(2) Uani d 1
C C3 0.2259(4) 0.6656(8) 0.5753(5) 0.1049(17) Uani d 1
H H3 0.2404 0.7876 0.6085 0.126 Uiso calc 1
C C4 0.2873(2) 0.5700(6) 0.4854(4) 0.0794(11) Uani d 1
C C5 0.2652(2) 0.3904(5) 0.4421(3) 0.0666(10) Uani d 1
C C6 0.1852(3) 0.3106(8) 0.4870(4) 0.0921(13) Uani d 1
H H6 0.1721 0.1855 0.4606 0.111 Uiso calc 1
C C7 0.0822(4) 0.7033(13) 0.7118(7) 0.178(4) Uani d 1
H H7A 0.0806 0.6477 0.8114 0.267 Uiso calc 1
H H7B 0.0216 0.7030 0.6630 0.267 Uiso calc 1
H H7C 0.1040 0.8312 0.7212 0.267 Uiso calc 1
C C8 0.3708(4) 0.6517(7) 0.4485(7) 0.1135(16) Uani d 1
H H8A 0.3942 0.5853 0.3638 0.170 Uiso calc 1
H H8B 0.4142 0.6433 0.5348 0.170 Uiso calc 1
H H8C 0.3612 0.7822 0.4217 0.170 Uiso calc 1
C C9 0.39175(19) 0.1749(4) 0.4154(3) 0.0519(8) Uani 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 0.0000 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
C9 N1 C5 121.9(2)
C9 N1 H1 119.1
C5 N1 H1 119.1
C9 N2 H2A 117(2)
C9 N2 H2B 115(3)
H2A N2 H2B 128(4)
C6 C1 C2 119.2(6)
C6 C1 H1A 120.4
C2 C1 H1A 120.4
C3 C2 C1 119.0(4)
C3 C2 C7 119.5(7)
C1 C2 C7 121.5(6)
C2 C3 C4 122.7(5)
C2 C3 H3 118.7
C4 C3 H3 118.7
C5 C4 C3 117.1(4)
C5 C4 C8 121.0(4)
C3 C4 C8 121.8(4)
C4 C5 C6 119.7(3)
C4 C5 N1 119.8(3)
C6 C5 N1 120.5(4)
C1 C6 C5 122.2(6)
C1 C6 H6 118.9
C5 C6 H6 118.9
C2 C7 H7A 109.5
C2 C7 H7B 109.5
H7A C7 H7B 109.5
C2 C7 H7C 109.5
H7A C7 H7C 109.5
H7B C7 H7C 109.5
C4 C8 H8A 109.5
C4 C8 H8B 109.5
H8A C8 H8B 109.5
C4 C8 H8C 109.5
H8A C8 H8C 109.5
H8B C8 H8C 109.5
O1 C9 N2 122.5(2)
O1 C9 N1 122.4(2)
N2 C9 N1 115.1(2)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C9 1.236(3)
N1 C9 1.340(4)
N1 C5 1.428(4)
N1 H1 0.8600
N2 C9 1.337(4)
N2 H2A 0.857(10)
N2 H2B 0.863(10)
C1 C6 1.351(7)
C1 C2 1.368(10)
C1 H1A 0.9300
C2 C3 1.348(9)
C2 C7 1.541(6)
C3 C4 1.406(6)
C3 H3 0.9300
C4 C5 1.358(6)
C4 C8 1.407(7)
C5 C6 1.377(6)
C6 H6 0.9300
C7 H7A 0.9600
C7 H7B 0.9600
C7 H7C 0.9600
C8 H8A 0.9600
C8 H8B 0.9600
C8 H8C 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
N1 H1 O1 4_565 0.86 2.23 2.941(3) 140
N2 H2A O1 4_565 0.860(10) 2.24(2) 2.985(3) 145(3)
N2 H2B O1 3_656 0.860(10) 2.120(10) 2.977(3) 173(4)
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
C6 C1 C2 C3 2.3(7)
C6 C1 C2 C7 -178.3(4)
C1 C2 C3 C4 0.5(7)
C7 C2 C3 C4 -178.9(4)
C2 C3 C4 C5 -1.6(6)
C2 C3 C4 C8 -178.1(5)
C3 C4 C5 C6 -0.1(5)
C8 C4 C5 C6 176.5(4)
C3 C4 C5 N1 -179.4(3)
C8 C4 C5 N1 -2.8(5)
C9 N1 C5 C4 90.7(4)
C9 N1 C5 C6 -88.6(4)
C2 C1 C6 C5 -4.1(7)
C4 C5 C6 C1 2.9(6)
N1 C5 C6 C1 -177.8(3)
C5 N1 C9 O1 6.1(5)
C5 N1 C9 N2 -174.4(3)
