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#$Date: 2016-02-13 14:50:18 +0200 (Sat, 13 Feb 2016) $
#$Revision: 176428 $
#$URL: svn://www.crystallography.net/cod/cif/1/10/10/1101000.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
loop_
_publ_author_name
'Hashimoto, Masao'
'Tajima, Fukue'
'Eda, Kazuo'
'Yamamura, Kimiaki'
'Okazaki, Tadashi'
_publ_section_title
;
 Exploration of plastic-like phases in alkylurea systems.
 A thermal and X-ray study
;
_journal_issue                   1-3
_journal_name_full               'Journal of Molecular Structure'
_journal_page_first              23
_journal_page_last               33
_journal_paper_doi               10.1016/j.molstruc.2004.08.008
_journal_volume                  734
_journal_year                    2005
_chemical_formula_moiety         'C9 H20 N2 O'
_chemical_formula_sum            'C9 H20 N2 O'
_chemical_formula_weight         172.27
_chemical_melting_point          374.6
_chemical_name_common            n-octylurea
_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
_cell_angle_alpha                90.00
_cell_angle_beta                 93.17(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   16.407(18)
_cell_length_b                   7.558(9)
_cell_length_c                   9.321(11)
_cell_measurement_reflns_used    635
_cell_measurement_temperature    360(2)
_cell_measurement_theta_max      22.561
_cell_measurement_theta_min      2.968
_cell_volume                     1154(2)
_diffrn_ambient_temperature      360(2)
_diffrn_measured_fraction_theta_full 0.674
_diffrn_measured_fraction_theta_max 0.674
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega 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  0.0697
_diffrn_reflns_av_sigmaI/netI    0.1026
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       5
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            2754
_diffrn_reflns_theta_full        27.20
_diffrn_reflns_theta_max         27.20
_diffrn_reflns_theta_min         2.49
_exptl_absorpt_coefficient_mu    0.065
_exptl_absorpt_correction_T_max  0.9820
_exptl_absorpt_correction_T_min  0.0382
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   'program SADABS ver. 2.03(Sheldrick)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    0.992
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             384
_exptl_crystal_size_max          0.53
_exptl_crystal_size_mid          0.41
_exptl_crystal_size_min          0.28
_refine_diff_density_max         0.306
_refine_diff_density_min         -0.203
_refine_diff_density_rms         0.084
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.781
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     122
_refine_ls_number_reflns         1734
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.781
_refine_ls_R_factor_all          0.2218
_refine_ls_R_factor_gt           0.1206
_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)+(0.2000P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2751
_refine_ls_wR_factor_ref         0.3131
_reflns_number_gt                561
_reflns_number_total             1734
_reflns_threshold_expression     >2sigma(I)
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               1101000
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_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_
_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 . . ?
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 . ?
