#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/50/2225072.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_2225072
loop_
_publ_author_name
'Saraswathi, B. S.'
'Gowda, B. Thimme'
'Foro, Sabine'
'Fuess, Hartmut'
_publ_section_title
;
 N-(4-Methylphenyl)succinimide
;
_journal_coeditor_code           NG2719
_journal_issue                   2
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o390
_journal_paper_doi               10.1107/S1600536810001546
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C11 H11 N O2'
_chemical_formula_moiety         'C11 H11 N O2'
_chemical_formula_sum            'C11 H11 N O2'
_chemical_formula_weight         189.21
_chemical_name_systematic
;
N-(4-Methylphenyl)succinimide
;
_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   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 109.35(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   13.543(3)
_cell_length_b                   5.6539(9)
_cell_length_c                   13.365(3)
_cell_measurement_reflns_used    1028
_cell_measurement_temperature    299(2)
_cell_measurement_theta_max      27.77
_cell_measurement_theta_min      2.60
_cell_volume                     965.6(4)
_computing_cell_refinement
;
CrysAlis RED (Oxford Diffraction, 2009)
;
_computing_data_collection
;
CrysAlis CCD (Oxford Diffraction, 2009)
;
_computing_data_reduction
;
CrysAlis RED (Oxford Diffraction, 2009)
;
_computing_molecular_graphics    'PLATON (Spek, 2009)'
_computing_publication_material  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      299(2)
_diffrn_measured_fraction_theta_full 0.981
_diffrn_measured_fraction_theta_max 0.981
_diffrn_measurement_device_type
;
Oxford Diffraction Xcalibur diffractometer
with a Sapphire CCD detector
;
_diffrn_measurement_method
;
Rotation method data acquisition using ω and φ 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  0.0195
_diffrn_reflns_av_sigmaI/netI    0.0322
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            3389
_diffrn_reflns_theta_full        26.36
_diffrn_reflns_theta_max         26.36
_diffrn_reflns_theta_min         3.09
_diffrn_standards_decay_%        0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.090
_exptl_absorpt_correction_T_max  0.9928
_exptl_absorpt_correction_T_min  0.9613
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(CrysAlis RED; Oxford Diffraction, 2009)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.302
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             400
_exptl_crystal_size_max          0.44
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.174
_refine_diff_density_min         -0.158
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.229
_refine_ls_hydrogen_treatment    refxyz
_refine_ls_matrix_type           full
_refine_ls_number_parameters     160
_refine_ls_number_reflns         1924
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.229
_refine_ls_R_factor_all          0.1139
_refine_ls_R_factor_gt           0.0682
_refine_ls_shift/su_max          0.017
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0241P)²+0.6535P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1185
_refine_ls_wR_factor_ref         0.1360
_reflns_number_gt                1262
_reflns_number_total             1924
_reflns_threshold_expression     I>2sigma(I)
_cod_data_source_file            ng2719.cif
_cod_data_source_block           I
_cod_original_cell_volume        965.6(3)
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2225072
_cod_database_fobs_code          2225072
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 0.25083(19) 0.2010(5) 0.2351(2) 0.0412(6) Uani d . 1 . .
C C2 0.2495(2) 0.0189(5) 0.3031(2) 0.0531(8) Uani d . 1 . .
H H2 0.293(2) -0.118(5) 0.306(2) 0.064 Uiso d . 1 . .
C C3 0.1863(3) 0.0374(6) 0.3657(2) 0.0602(9) Uani d . 1 . .
H H3 0.187(2) -0.089(5) 0.412(2) 0.072 Uiso d . 1 . .
C C4 0.1243(2) 0.2332(6) 0.3618(2) 0.0547(8) Uani d . 1 . .
C C5 0.1272(2) 0.4126(6) 0.2926(3) 0.0556(8) Uani d . 1 . .
H H5 0.086(2) 0.550(5) 0.290(2) 0.067 Uiso d . 1 . .
C C6 0.1896(2) 0.3988(5) 0.2296(2) 0.0486(7) Uani d . 1 . .
H H6 0.193(2) 0.523(5) 0.182(2) 0.058 Uiso d . 1 . .
C C7 0.3049(2) 0.0071(5) 0.0936(2) 0.0484(7) Uani d . 1 . .
C C8 0.3859(3) 0.0509(7) 0.0415(3) 0.0609(9) Uani d . 1 . .
H H8A 0.440(2) -0.074(6) 0.068(2) 0.073 Uiso d . 1 . .
H H8B 0.353(2) 0.041(6) -0.037(3) 0.073 Uiso d . 1 . .
C C9 0.4333(3) 0.2887(7) 0.0825(3) 0.0631(9) Uani d . 1 . .
H H9A 0.510(2) 0.288(5) 0.109(2) 0.076 Uiso d . 1 . .
H H9B 0.411(2) 0.408(6) 0.032(2) 0.076 Uiso d . 1 . .
C C10 0.3921(2) 0.3502(5) 0.1706(2) 0.0512(7) Uani d . 1 . .
C C11 0.0552(3) 0.2544(9) 0.4292(3) 0.0859(14) Uani d . 1 . .
H H11A -0.013(3) 0.301(7) 0.394(3) 0.103 Uiso d . 1 . .
H H11B 0.085(3) 0.350(7) 0.492(3) 0.103 Uiso d . 1 . .
H H11C 0.047(3) 0.100(7) 0.452(3) 0.103 Uiso d . 1 . .
N N1 0.31460(16) 0.1858(4) 0.16839(17) 0.0437(6) Uani d . 1 . .
O O1 0.24145(17) -0.1496(4) 0.07658(16) 0.0637(6) Uani d . 1 . .
O O2 0.41793(16) 0.5111(4) 0.23272(19) 0.0714(7) 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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C2 C1 C6 . . 120.1(3) ?
C2 C1 N1 . . 120.5(3) ?
C6 C1 N1 . . 119.3(2) ?
C1 C2 C3 . . 119.2(3) ?
C1 C2 H2 . . 119.0(17) ?
C3 C2 H2 . . 121.7(17) ?
C4 C3 C2 . . 121.8(3) ?
C4 C3 H3 . . 120.0(18) ?
C2 C3 H3 . . 118.2(19) ?
C3 C4 C5 . . 117.6(3) ?
C3 C4 C11 . . 122.2(3) ?
C5 C4 C11 . . 120.3(3) ?
C6 C5 C4 . . 121.7(3) ?
C6 C5 H5 . . 119.5(19) ?
C4 C5 H5 . . 118.7(18) ?
C1 C6 C5 . . 119.5(3) ?
C1 C6 H6 . . 118.4(16) ?
C5 C6 H6 . . 122.1(17) ?
O1 C7 N1 . . 124.1(3) ?
O1 C7 C8 . . 128.3(3) ?
N1 C7 C8 . . 107.6(3) ?
C7 C8 C9 . . 105.5(3) ?
C7 C8 H8A . . 106.5(18) ?
C9 C8 H8A . . 109.3(18) ?
C7 C8 H8B . . 109.8(17) ?
C9 C8 H8B . . 114.8(19) ?
H8A C8 H8B . . 111(3) ?
C10 C9 C8 . . 105.5(3) ?
C10 C9 H9A . . 110.0(18) ?
C8 C9 H9A . . 113.6(19) ?
C10 C9 H9B . . 106.7(19) ?
C8 C9 H9B . . 112.5(19) ?
H9A C9 H9B . . 108(3) ?
O2 C10 N1 . . 124.3(3) ?
O2 C10 C9 . . 128.1(3) ?
N1 C10 C9 . . 107.5(3) ?
C4 C11 H11A . . 116(2) ?
C4 C11 H11B . . 114(2) ?
H11A C11 H11B . . 110(3) ?
C4 C11 H11C . . 106(2) ?
H11A C11 H11C . . 103(3) ?
H11B C11 H11C . . 107(3) ?
C10 N1 C7 . . 112.9(2) ?
C10 N1 C1 . . 123.4(2) ?
C7 N1 C1 . . 123.7(2) ?
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 . 1.378(4) ?
C1 C6 . 1.380(4) ?
C1 N1 . 1.434(3) ?
C2 C3 . 1.385(4) ?
C2 H2 . 0.96(3) ?
C3 C4 . 1.380(4) ?
C3 H3 . 0.94(3) ?
C4 C5 . 1.381(4) ?
C4 C11 . 1.504(5) ?
C5 C6 . 1.380(4) ?
C5 H5 . 0.95(3) ?
C6 H6 . 0.95(3) ?
C7 O1 . 1.202(3) ?
C7 N1 . 1.397(3) ?
C7 C8 . 1.502(4) ?
C8 C9 . 1.511(5) ?
C8 H8A . 0.99(3) ?
C8 H8B . 0.99(3) ?
C9 C10 . 1.502(4) ?
C9 H9A . 0.99(3) ?
C9 H9B . 0.94(3) ?
C10 O2 . 1.203(3) ?
C10 N1 . 1.394(3) ?
C11 H11A . 0.92(4) ?
C11 H11B . 0.97(4) ?
C11 H11C . 0.95(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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C6 C1 C2 C3 . . . . -0.1(4) ?
N1 C1 C2 C3 . . . . -179.3(3) ?
C1 C2 C3 C4 . . . . 0.1(5) ?
C2 C3 C4 C5 . . . . -0.1(5) ?
C2 C3 C4 C11 . . . . 179.8(3) ?
C3 C4 C5 C6 . . . . -0.1(5) ?
C11 C4 C5 C6 . . . . -180.0(3) ?
C2 C1 C6 C5 . . . . 0.0(4) ?
N1 C1 C6 C5 . . . . 179.2(3) ?
C4 C5 C6 C1 . . . . 0.1(5) ?
O1 C7 C8 C9 . . . . 172.3(3) ?
N1 C7 C8 C9 . . . . -7.4(3) ?
C7 C8 C9 C10 . . . . 10.1(3) ?
C8 C9 C10 O2 . . . . 171.3(3) ?
C8 C9 C10 N1 . . . . -9.4(3) ?
O2 C10 N1 C7 . . . . -175.6(3) ?
C9 C10 N1 C7 . . . . 5.1(3) ?
O2 C10 N1 C1 . . . . 5.1(4) ?
C9 C10 N1 C1 . . . . -174.2(2) ?
O1 C7 N1 C10 . . . . -178.2(3) ?
C8 C7 N1 C10 . . . . 1.5(3) ?
O1 C7 N1 C1 . . . . 1.1(4) ?
C8 C7 N1 C1 . . . . -179.2(2) ?
C2 C1 N1 C10 . . . . -121.8(3) ?
C6 C1 N1 C10 . . . . 59.0(3) ?
C2 C1 N1 C7 . . . . 59.0(3) ?
C6 C1 N1 C7 . . . . -120.2(3) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 67872
