#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/88/2228892.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_2228892
loop_
_publ_author_name
'Meng, Shuang-Ming'
'Wang, Ke-Wei'
'Xie, Hai'
'Fan, Yue-Qin'
'Guo, Yong'
_publ_section_title
;
 N-Phenylmorpholine-4-carboxamide
;
_journal_coeditor_code           SU2236
_journal_issue                   1
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o225
_journal_paper_doi               10.1107/S1600536810052207
_journal_volume                  67
_journal_year                    2011
_chemical_formula_iupac          'C11 H14 N2 O2'
_chemical_formula_moiety         'C11 H14 N2 O2'
_chemical_formula_sum            'C11 H14 N2 O2'
_chemical_formula_weight         206.24
_chemical_name_systematic
;
N-Phenylmorpholine-4-carboxamide
;
_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                 104.205(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.0907(10)
_cell_length_b                   15.754(2)
_cell_length_c                   8.4529(11)
_cell_measurement_reflns_used    5309
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      26.1
_cell_measurement_theta_min      2.6
_cell_volume                     1044.5(2)
_computing_cell_refinement       'SAINT (Bruker, 2007)'
_computing_data_collection       'SMART (Bruker, 2007)'
_computing_data_reduction        'SAINT (Bruker, 2007)'
_computing_molecular_graphics    'SHELXTL-Plus (Sheldrick, 2008)'
_computing_publication_material  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker SMART APEX CCD'
_diffrn_measurement_method       ω
_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  0.0162
_diffrn_reflns_av_sigmaI/netI    0.0201
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            5309
_diffrn_reflns_theta_full        26.05
_diffrn_reflns_theta_max         26.05
_diffrn_reflns_theta_min         2.59
_diffrn_standards_decay_%        0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.092
_exptl_absorpt_correction_T_max  0.981
_exptl_absorpt_correction_T_min  0.976
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2001)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.312
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             440
_exptl_crystal_size_max          0.29
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.19
_refine_diff_density_max         0.132
_refine_diff_density_min         -0.178
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     139
_refine_ls_number_reflns         2056
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.041
_refine_ls_R_factor_all          0.0524
_refine_ls_R_factor_gt           0.0401
_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)+(0.0510P)²+0.1766P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0971
_refine_ls_wR_factor_ref         0.1050
_reflns_number_gt                1633
_reflns_number_total             2056
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            su2236.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2228892
_cod_database_fobs_code          2228892
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_disorder_assembly
_atom_site_disorder_group
C C1 0.32831(18) 0.27851(9) 0.53510(15) 0.0363(3) Uani d . 1 . .
C C6 0.21670(19) 0.23577(9) 0.60820(17) 0.0423(4) Uani d . 1 . .
H H006 0.2379 0.1796 0.6410 0.051 Uiso calc R 1 . .
C C2 0.2934(2) 0.36162(9) 0.48415(18) 0.0446(4) Uani d . 1 . .
H H007 0.3679 0.3909 0.4358 0.054 Uiso calc R 1 . .
C C7 0.56729(17) 0.17667(8) 0.59477(16) 0.0354(3) Uani d . 1 . .
C C11 0.79490(19) 0.07168(10) 0.61799(19) 0.0466(4) Uani d . 1 . .
H H00A 0.7747 0.0651 0.7258 0.056 Uiso calc R 1 . .
H H00B 0.9098 0.0932 0.6306 0.056 Uiso calc R 1 . .
C C5 0.0740(2) 0.27684(11) 0.6320(2) 0.0533(4) Uani d . 1 . .
H H010 0.0011 0.2486 0.6838 0.064 Uiso calc R 1 . .
C C9 0.6653(2) 0.04917(11) 0.2800(2) 0.0532(4) Uani d . 1 . .
H H01A 0.5540 0.0256 0.2783 0.064 Uiso calc R 1 . .
H H01B 0.6755 0.0528 0.1683 0.064 Uiso calc R 1 . .
C C8 0.6786(2) 0.13675(10) 0.35298(18) 0.0515(4) Uani d . 1 . .
H H01C 0.7849 0.1629 0.3450 0.062 Uiso calc R 1 . .
H H01D 0.5854 0.1716 0.2929 0.062 Uiso calc R 1 . .
C C10 0.7776(2) -0.01294(10) 0.5331(2) 0.0535(4) Uani d . 1 . .
H H01E 0.8650 -0.0511 0.5929 0.064 Uiso calc R 1 . .
H H01F 0.6674 -0.0373 0.5327 0.064 Uiso calc R 1 . .
C C4 0.0387(2) 0.35911(12) 0.5799(2) 0.0633(5) Uani d . 1 . .
H H014 -0.0584 0.3862 0.5951 0.076 Uiso calc R 1 . .
C C3 0.1479(2) 0.40080(11) 0.5054(2) 0.0587(5) Uani d . 1 . .
H H015 0.1236 0.4561 0.4687 0.070 Uiso calc R 1 . .
N N2 0.67253(16) 0.13193(8) 0.52338(14) 0.0450(3) Uani d . 1 . .
O O1 0.55772(13) 0.16176(6) 0.73527(11) 0.0438(3) Uani d . 1 . .
O O2 0.79327(14) -0.00542(7) 0.36958(15) 0.0565(3) Uani d . 1 . .
N N1 0.47270(16) 0.23906(8) 0.50123(15) 0.0425(3) Uani d . 1 . .
H H1N 0.505(2) 0.2590(11) 0.421(2) 0.051 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 0.0000 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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C2 C1 C6 . . 119.46(13) ?
C2 C1 N1 . . 117.91(13) ?
C6 C1 N1 . . 122.52(12) ?
C5 C6 C1 . . 119.76(14) ?
C5 C6 H006 . . 120.1 ?
C1 C6 H006 . . 120.1 ?
C3 C2 C1 . . 119.86(15) ?
C3 C2 H007 . . 120.1 ?
C1 C2 H007 . . 120.1 ?
O1 C7 N2 . . 121.67(13) ?
O1 C7 N1 . . 122.31(12) ?
N2 C7 N1 . . 116.02(12) ?
N2 C11 C10 . . 110.11(13) ?
N2 C11 H00A . . 109.6 ?
C10 C11 H00A . . 109.6 ?
N2 C11 H00B . . 109.6 ?
C10 C11 H00B . . 109.6 ?
H00A C11 H00B . . 108.2 ?
C4 C5 C6 . . 120.69(15) ?
C4 C5 H010 . . 119.7 ?
C6 C5 H010 . . 119.7 ?
O2 C9 C8 . . 111.64(14) ?
O2 C9 H01A . . 109.3 ?
C8 C9 H01A . . 109.3 ?
O2 C9 H01B . . 109.3 ?
C8 C9 H01B . . 109.3 ?
H01A C9 H01B . . 108.0 ?
N2 C8 C9 . . 109.95(13) ?
N2 C8 H01C . . 109.7 ?
C9 C8 H01C . . 109.7 ?
N2 C8 H01D . . 109.7 ?
C9 C8 H01D . . 109.7 ?
H01C C8 H01D . . 108.2 ?
O2 C10 C11 . . 111.67(13) ?
O2 C10 H01E . . 109.3 ?
C11 C10 H01E . . 109.3 ?
O2 C10 H01F . . 109.3 ?
C11 C10 H01F . . 109.3 ?
H01E C10 H01F . . 107.9 ?
C3 C4 C5 . . 119.41(15) ?
C3 C4 H014 . . 120.3 ?
C5 C4 H014 . . 120.3 ?
C4 C3 C2 . . 120.78(15) ?
C4 C3 H015 . . 119.6 ?
C2 C3 H015 . . 119.6 ?
C7 N2 C8 . . 126.22(12) ?
C7 N2 C11 . . 120.64(12) ?
C8 N2 C11 . . 113.14(12) ?
C9 O2 C10 . . 110.01(11) ?
C7 N1 C1 . . 124.79(12) ?
C7 N1 H1N . . 119.4(12) ?
C1 N1 H1N . . 115.7(12) ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
C1 C2 . 1.386(2) ?
C1 C6 . 1.387(2) ?
C1 N1 . 1.4132(18) ?
C6 C5 . 1.380(2) ?
C6 H006 . 0.9300 ?
C2 C3 . 1.379(2) ?
C2 H007 . 0.9300 ?
C7 O1 . 1.2315(16) ?
C7 N2 . 1.3559(18) ?
C7 N1 . 1.3711(18) ?
C11 N2 . 1.4601(18) ?
C11 C10 . 1.504(2) ?
C11 H00A . 0.9700 ?
C11 H00B . 0.9700 ?
C5 C4 . 1.376(2) ?
C5 H010 . 0.9300 ?
C9 O2 . 1.414(2) ?
C9 C8 . 1.504(2) ?
C9 H01A . 0.9700 ?
C9 H01B . 0.9700 ?
C8 N2 . 1.4553(18) ?
C8 H01C . 0.9700 ?
C8 H01D . 0.9700 ?
C10 O2 . 1.424(2) ?
C10 H01E . 0.9700 ?
C10 H01F . 0.9700 ?
C4 C3 . 1.372(2) ?
C4 H014 . 0.9300 ?
C3 H015 . 0.9300 ?
N1 H1N . 0.844(17) ?
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 H1N O1 4_565 0.844(17) 2.130(18) 2.9543(16) 165.3(16)
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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C2 C1 C6 C5 . . . . -1.2(2) ?
N1 C1 C6 C5 . . . . -177.35(13) ?
C6 C1 C2 C3 . . . . -0.5(2) ?
N1 C1 C2 C3 . . . . 175.89(14) ?
C1 C6 C5 C4 . . . . 1.8(2) ?
O2 C9 C8 N2 . . . . -55.97(18) ?
N2 C11 C10 O2 . . . . 54.81(17) ?
C6 C5 C4 C3 . . . . -0.8(3) ?
C5 C4 C3 C2 . . . . -0.9(3) ?
C1 C2 C3 C4 . . . . 1.5(3) ?
O1 C7 N2 C8 . . . . 171.82(14) ?
N1 C7 N2 C8 . . . . -8.1(2) ?
O1 C7 N2 C11 . . . . -8.0(2) ?
N1 C7 N2 C11 . . . . 172.05(13) ?
C9 C8 N2 C7 . . . . -128.09(16) ?
C9 C8 N2 C11 . . . . 51.77(18) ?
C10 C11 N2 C7 . . . . 128.49(15) ?
C10 C11 N2 C8 . . . . -51.38(18) ?
C8 C9 O2 C10 . . . . 60.27(17) ?
C11 C10 O2 C9 . . . . -59.74(17) ?
O1 C7 N1 C1 . . . . -16.0(2) ?
N2 C7 N1 C1 . . . . 163.93(13) ?
C2 C1 N1 C7 . . . . 150.53(14) ?
C6 C1 N1 C7 . . . . -33.2(2) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 303007
