#------------------------------------------------------------------------------
#$Date: 2010-01-30 13:59:17 +0000 (Sat, 30 Jan 2010) $
#$Revision: 966 $
#$URL: svn://www.crystallography.net/cod/cif/1/1101000.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_1101000
_journal_name_full           'Journal of Molecular Structure'
_space_group_IT_number           14
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_[local]_cod_cif_authors_sg_H-M  'P 21/c'
loop_
_publ_author_name
    'Masao Hashimoto'
    'Fukue Tajima'
    'Kazuo Eda'
    'Kimiaki Yamamura'
    'Tadashi Okazaki'
_chemical_name_common             'n-octylurea'
_chemical_melting_point           374.6
_chemical_formula_moiety          'C9 H20 N2 O'
_chemical_formula_sum      'C9 H20 N2 O'
_chemical_formula_weight          172.27
_symmetry_cell_setting            monoclinic
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'
_cell_length_a                    16.407(18)
_cell_length_b                    7.558(9)
_cell_length_c                    9.321(11)
_cell_angle_alpha                 90.00
_cell_angle_beta                  93.17(3)
_cell_angle_gamma                 90.00
_cell_volume                      1154(2)
_cell_formula_units_Z             4
_cell_measurement_temperature     360(2)
_cell_measurement_reflns_used     635
_cell_measurement_theta_min       2.968
_cell_measurement_theta_max       22.561
_exptl_crystal_description        ?
_exptl_crystal_colour             colorless
_exptl_crystal_size_max           0.53
_exptl_crystal_size_mid           0.41
_exptl_crystal_size_min           0.28
_exptl_crystal_density_meas       ?
_exptl_crystal_density_diffrn     0.992
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000              384
_exptl_absorpt_coefficient_mu     0.065
_exptl_absorpt_correction_type    empirical
_exptl_absorpt_correction_T_min   0.0382
_exptl_absorpt_correction_T_max   0.9820
_exptl_absorpt_process_details    'program SADABS ver. 2.03(Sheldrick)'
_diffrn_ambient_temperature       360(2)
_diffrn_radiation_wavelength      0.71073
_diffrn_radiation_type            MoK\a
_diffrn_radiation_source          'fine-focus sealed tube'
_diffrn_radiation_monochromator   graphite
_diffrn_measurement_device_type   'CCD area detector'
_diffrn_measurement_method        'phi and omega scans'
_diffrn_detector_area_resol_mean  ?
_diffrn_standards_number          ?
_diffrn_standards_interval_count  ?
_diffrn_standards_interval_time   ?
_diffrn_standards_decay_%         ?
_diffrn_reflns_number             2754
_diffrn_reflns_av_R_equivalents   0.0697
_diffrn_reflns_av_sigmaI/netI     0.1026
_diffrn_reflns_limit_h_min        -11
_diffrn_reflns_limit_h_max        15
_diffrn_reflns_limit_k_min        -9
_diffrn_reflns_limit_k_max        9
_diffrn_reflns_limit_l_min        -11
_diffrn_reflns_limit_l_max        5
_diffrn_reflns_theta_min          2.49
_diffrn_reflns_theta_max          27.20
_reflns_number_total              1734
_reflns_number_gt                 561
_reflns_threshold_expression      >2sigma(I)
_refine_ls_structure_factor_coef  Fsqd
_refine_ls_matrix_type            full
_refine_ls_weighting_scheme       calc
_refine_ls_weighting_details
 'calc w=1/[\s^2^(Fo^2^)+(0.2000P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary      direct
_atom_sites_solution_secondary    difmap
_atom_sites_solution_hydrogens    geom
_refine_ls_hydrogen_treatment     mixed
_refine_ls_extinction_method      none
_refine_ls_extinction_coef        ?
_refine_ls_number_reflns          1734
_refine_ls_number_parameters      122
_refine_ls_number_restraints      0
_refine_ls_R_factor_all           0.2218
_refine_ls_R_factor_gt            0.1206
_refine_ls_wR_factor_ref          0.3131
_refine_ls_wR_factor_gt           0.2751
_refine_ls_goodness_of_fit_ref    0.781
_refine_ls_restrained_S_all       0.781
_refine_ls_shift/su_max           0.000
_refine_ls_shift/su_mean          0.000
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 0.6362(4) 0.5016(7) 0.0477(5) 0.149(3) Uani 1 1 d . . .
H1A H 0.5934 0.5555 -0.0137 0.178 Uiso 1 1 calc R . .
H1B H 0.6752 0.4486 -0.0139 0.178 Uiso 1 1 calc R . .
C2 C 0.6768(5) 0.6381(8) 0.1339(6) 0.156(3) Uani 1 1 d . . .
H2A H 0.7188 0.5832 0.1962 0.187 Uiso 1 1 calc R . .
H2B H 0.6374 0.6910 0.1949 0.187 Uiso 1 1 calc R . .
C3 C 0.7149(5) 0.7812(9) 0.0509(7) 0.177(3) Uani 1 1 d . . .
H3A H 0.7507 0.7273 -0.0160 0.212 Uiso 1 1 calc R . .
H3B H 0.6721 0.8427 -0.0052 0.212 Uiso 1 1 calc R . .
C4 C 0.7626(6) 0.9135(12) 0.1386(7) 0.198(4) Uani 1 1 d . . .
H4A H 0.7256 0.9739 0.1999 0.237 Uiso 1 1 calc R . .
H4B H 0.8021 0.8505 0.2009 0.237 Uiso 1 1 calc R . .
C5 C 0.8063(7) 1.0476(14) 0.0589(10) 0.249(5) Uani 1 1 d . . .
H5A H 0.8437 0.9876 -0.0018 0.299 Uiso 1 1 calc R . .
H5B H 0.7670 1.1105 -0.0036 0.299 Uiso 1 1 calc R . .
C6 C 0.8524(9) 1.1769(18) 0.1463(14) 0.306(7) Uani 1 1 d . . .
H6A H 0.8147 1.2284 0.2112 0.367 Uiso 1 1 calc R . .
H6B H 0.8924 1.1113 0.2054 0.367 Uiso 1 1 calc R . .
C7 C 0.8939(11) 1.318(3) 0.0854(19) 0.348(10) Uani 1 1 d . . .
C8A C 0.936(2) 1.451(4) 0.181(3) 0.205(11) Uani 0.35 1 d P . .
C8B C 0.979(2) 1.278(8) 0.128(6) 0.54(4) Uani 0.65 1 d P . .
C1U C 0.5651(3) 0.2237(7) 0.0761(4) 0.117(2) Uani 1 1 d . . .
N1 N 0.6008(3) 0.3643(6) 0.1321(4) 0.130(2) Uani 1 1 d . . .
N2 N 0.5355(3) 0.1071(5) 0.1659(3) 0.133(2) Uani 1 1 d . . .
H3 H 0.5116 0.0130 0.1330 0.160 Uiso 1 1 calc R . .
H2 H 0.5401 0.1256 0.2571 0.160 Uiso 1 1 calc R . .
O1 O 0.5594(2) 0.2010(4) -0.0577(2) 0.1253(17) Uani 1 1 d . . .
H1 H 0.608(3) 0.388(5) 0.232(5) 0.121(14) Uiso 1 1 d . . .
loop_
 _atom_site_aniso_label
 _atom_site_aniso_U_11
 _atom_site_aniso_U_22
 _atom_site_aniso_U_33
 _atom_site_aniso_U_23
 _atom_site_aniso_U_13
 _atom_site_aniso_U_12
C1 0.260(8) 0.126(4) 0.061(3) -0.003(3) 0.010(4) -0.026(4)
C2 0.234(9) 0.154(5) 0.080(4) -0.003(4) 0.011(4) -0.027(5)
C3 0.298(10) 0.142(5) 0.091(4) -0.007(4) 0.023(5) -0.047(6)
C4 0.284(11) 0.188(7) 0.121(5) -0.008(6) 0.014(6) -0.055(7)
C5 0.364(15) 0.230(9) 0.156(7) -0.011(7) 0.040(8) -0.125(10)
C6 0.43(2) 0.289(13) 0.201(12) -0.009(10) 0.027(12) -0.168(14)
C7 0.38(3) 0.42(3) 0.246(16) 0.029(14) 0.051(18) -0.14(2)
C8A 0.08(3) 0.30(3) 0.22(3) -0.06(2) -0.060(17) -0.04(2)
C8B 0.27(5) 0.66(7) 0.70(7) 0.28(6) 0.14(5) 0.05(5)
C1U 0.213(7) 0.102(3) 0.037(2) -0.003(2) 0.007(3) 0.007(4)
N1 0.237(6) 0.123(3) 0.0306(18) -0.009(2) 0.010(2) -0.028(3)
N2 0.256(6) 0.119(3) 0.0249(16) 0.0054(17) 0.009(2) -0.021(3)
O1 0.233(5) 0.125(2) 0.0166(13) -0.0048(13) -0.0044(16) -0.012(2)
_geom_special_details
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
 _geom_bond_atom_site_label_1
 _geom_bond_atom_site_label_2
 _geom_bond_distance
 _geom_bond_site_symmetry_2
 _geom_bond_publ_flag
C1 N1 1.443(6) . ?
C1 C2 1.448(8) . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C2 C3 1.487(7) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C3 C4 1.487(9) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C4 C5 1.468(9) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C5 C6 1.456(12) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C6 C7 1.401(18) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C7 C8B 1.46(4) . ?
C7 C8A 1.49(2) . ?
C1U O1 1.257(5) . ?
C1U N1 1.308(6) . ?
C1U N2 1.326(5) . ?
N1 H1 0.95(5) . ?
N2 H3 0.8600 . ?
N2 H2 0.8600 . ?
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
 _geom_angle_publ_flag
N1 C1 C2 113.3(4) . . ?
N1 C1 H1A 108.9 . . ?
C2 C1 H1A 108.9 . . ?
N1 C1 H1B 108.9 . . ?
C2 C1 H1B 108.9 . . ?
H1A C1 H1B 107.7 . . ?
C1 C2 C3 115.0(5) . . ?
C1 C2 H2A 108.5 . . ?
C3 C2 H2A 108.5 . . ?
C1 C2 H2B 108.5 . . ?
C3 C2 H2B 108.5 . . ?
H2A C2 H2B 107.5 . . ?
C4 C3 C2 115.2(6) . . ?
C4 C3 H3A 108.5 . . ?
C2 C3 H3A 108.5 . . ?
C4 C3 H3B 108.5 . . ?
C2 C3 H3B 108.5 . . ?
H3A C3 H3B 107.5 . . ?
C5 C4 C3 116.3(7) . . ?
C5 C4 H4A 108.2 . . ?
C3 C4 H4A 108.2 . . ?
C5 C4 H4B 108.2 . . ?
C3 C4 H4B 108.2 . . ?
H4A C4 H4B 107.4 . . ?
C6 C5 C4 115.7(9) . . ?
C6 C5 H5A 108.4 . . ?
C4 C5 H5A 108.4 . . ?
C6 C5 H5B 108.4 . . ?
C4 C5 H5B 108.4 . . ?
H5A C5 H5B 107.4 . . ?
C7 C6 C5 122.2(13) . . ?
C7 C6 H6A 106.8 . . ?
C5 C6 H6A 106.8 . . ?
C7 C6 H6B 106.8 . . ?
C5 C6 H6B 106.8 . . ?
H6A C6 H6B 106.6 . . ?
C6 C7 C8B 102(3) . . ?
C6 C7 C8A 119.4(18) . . ?
C8B C7 C8A 64(3) . . ?
O1 C1U N1 120.9(4) . . ?
O1 C1U N2 121.7(5) . . ?
N1 C1U N2 117.4(4) . . ?
C1U N1 C1 123.5(4) . . ?
C1U N1 H1 125(3) . . ?
C1 N1 H1 112(3) . . ?
C1U N2 H3 120.0 . . ?
C1U N2 H2 120.0 . . ?
H3 N2 H2 120.0 . . ?
_diffrn_measured_fraction_theta_max    0.674
_diffrn_reflns_theta_full              27.20
_diffrn_measured_fraction_theta_full   0.674
_refine_diff_density_max    0.306
_refine_diff_density_min   -0.203
_refine_diff_density_rms    0.084
_cod_database_code 1101000