#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/56/2225602.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_2225602
loop_
_publ_author_name
'Saraswathi, B. S.'
'Gowda, B. Thimme'
'Foro, Sabine'
'Fuess, Hartmut'
_publ_section_title
;
 N-(2,3-Dimethylphenyl)succinimide
;
_journal_coeditor_code           NG2748
_journal_issue                   4
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o919
_journal_paper_doi               10.1107/S160053681001055X
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C12 H13 N O2'
_chemical_formula_moiety         'C12 H13 N O2'
_chemical_formula_sum            'C12 H13 N O2'
_chemical_formula_weight         203.23
_chemical_name_systematic
;
N-(2,3-Dimethylphenyl)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   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 91.992(8)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   6.0600(5)
_cell_length_b                   16.429(2)
_cell_length_c                   10.5930(10)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    299(2)
_cell_measurement_theta_max      17.98
_cell_measurement_theta_min      5.39
_cell_volume                     1054.00(18)
_computing_cell_refinement       'CAD-4-PC (Enraf--Nonius, 1996)'
_computing_data_collection       'CAD-4-PC (Enraf--Nonius, 1996)'
_computing_data_reduction        'REDU4 (Stoe & Cie, 1987)'
_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 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Enraf--Nonius CAD-4'
_diffrn_measurement_method       ω/2θ
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54180
_diffrn_reflns_av_R_equivalents  0.0159
_diffrn_reflns_av_sigmaI/netI    0.0232
_diffrn_reflns_limit_h_max       1
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       0
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            2096
_diffrn_reflns_theta_full        66.90
_diffrn_reflns_theta_max         66.90
_diffrn_reflns_theta_min         4.97
_diffrn_standards_decay_%        1.0
_diffrn_standards_interval_time  120
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.709
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.281
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             432
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.179
_refine_diff_density_min         -0.205
_refine_ls_extinction_coef       0.0081(9)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL97 (Sheldrick, 2008)'
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     139
_refine_ls_number_reflns         1883
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.046
_refine_ls_R_factor_all          0.0577
_refine_ls_R_factor_gt           0.0410
_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)+(0.0595P)²+0.2594P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1127
_refine_ls_wR_factor_ref         0.1219
_reflns_number_gt                1472
_reflns_number_total             1883
_reflns_threshold_expression     I>2sigma(I)
_cod_data_source_file            ng2748.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2225602
_cod_database_fobs_code          2225602
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 0.0295(3) 0.64329(10) 0.78424(14) 0.0372(4) Uani d . 1 . .
C C2 0.1636(3) 0.60330(10) 0.70029(15) 0.0376(4) Uani d . 1 . .
C C3 0.1134(3) 0.61237(11) 0.57082(15) 0.0452(4) Uani d . 1 . .
C C4 -0.0697(3) 0.65748(12) 0.53242(17) 0.0546(5) Uani d . 1 . .
H H4 -0.1026 0.6632 0.4465 0.066 Uiso calc R 1 . .
C C5 -0.2041(3) 0.69410(12) 0.61716(19) 0.0557(5) Uani d . 1 . .
H H5 -0.3281 0.7230 0.5888 0.067 Uiso calc R 1 . .
C C6 -0.1541(3) 0.68768(11) 0.74460(18) 0.0467(4) Uani d . 1 . .
H H6 -0.2424 0.7128 0.8031 0.056 Uiso calc R 1 . .
C C7 0.2655(3) 0.67879(11) 0.97290(16) 0.0449(4) Uani d . 1 . .
C C8 0.2745(3) 0.65793(14) 1.11109(17) 0.0579(5) Uani d . 1 . .
H H8A 0.2780 0.7069 1.1622 0.069 Uiso calc R 1 . .
H H8B 0.4045 0.6256 1.1324 0.069 Uiso calc R 1 . .
C C9 0.0665(4) 0.60978(13) 1.13227(17) 0.0567(5) Uani d . 1 . .
H H9A 0.1021 0.5571 1.1689 0.068 Uiso calc R 1 . .
H H9B -0.0287 0.6388 1.1887 0.068 Uiso calc R 1 . .
C C10 -0.0448(3) 0.59991(11) 1.00467(17) 0.0461(4) Uani d . 1 . .
C C11 0.3529(3) 0.55084(11) 0.74623(17) 0.0478(5) Uani d . 1 . .
H H11A 0.3393 0.5398 0.8346 0.057 Uiso calc R 1 . .
H H11B 0.4896 0.5787 0.7332 0.057 Uiso calc R 1 . .
H H11C 0.3509 0.5005 0.7002 0.057 Uiso calc R 1 . .
C C12 0.2559(4) 0.57447(15) 0.47345(18) 0.0657(6) Uani d . 1 . .
H H12A 0.2417 0.5163 0.4767 0.079 Uiso calc R 1 . .
H H12B 0.4072 0.5894 0.4905 0.079 Uiso calc R 1 . .
H H12C 0.2098 0.5935 0.3910 0.079 Uiso calc R 1 . .
N N1 0.0830(2) 0.63939(9) 0.91715(12) 0.0393(4) Uani d . 1 . .
O O1 0.3887(2) 0.72166(9) 0.91606(13) 0.0598(4) Uani d . 1 . .
O O2 -0.2143(2) 0.56450(9) 0.97796(13) 0.0629(4) 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 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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
C6 C1 C2 . . 122.47(15) ?
C6 C1 N1 . . 118.25(15) ?
C2 C1 N1 . . 119.28(14) ?
C1 C2 C3 . . 117.62(15) ?
C1 C2 C11 . . 121.38(15) ?
C3 C2 C11 . . 120.98(15) ?
C4 C3 C2 . . 119.26(17) ?
C4 C3 C12 . . 119.62(17) ?
C2 C3 C12 . . 121.12(17) ?
C5 C4 C3 . . 122.07(17) ?
C5 C4 H4 . . 119.0 ?
C3 C4 H4 . . 119.0 ?
C4 C5 C6 . . 119.49(17) ?
C4 C5 H5 . . 120.3 ?
C6 C5 H5 . . 120.3 ?
C5 C6 C1 . . 119.02(17) ?
C5 C6 H6 . . 120.5 ?
C1 C6 H6 . . 120.5 ?
O1 C7 N1 . . 123.82(16) ?
O1 C7 C8 . . 128.24(17) ?
N1 C7 C8 . . 107.95(15) ?
C7 C8 C9 . . 105.16(15) ?
C7 C8 H8A . . 110.7 ?
C9 C8 H8A . . 110.7 ?
C7 C8 H8B . . 110.7 ?
C9 C8 H8B . . 110.7 ?
H8A C8 H8B . . 108.8 ?
C10 C9 C8 . . 105.92(15) ?
C10 C9 H9A . . 110.6 ?
C8 C9 H9A . . 110.6 ?
C10 C9 H9B . . 110.6 ?
C8 C9 H9B . . 110.6 ?
H9A C9 H9B . . 108.7 ?
O2 C10 N1 . . 123.97(17) ?
O2 C10 C9 . . 128.09(17) ?
N1 C10 C9 . . 107.93(15) ?
C2 C11 H11A . . 109.5 ?
C2 C11 H11B . . 109.5 ?
H11A C11 H11B . . 109.5 ?
C2 C11 H11C . . 109.5 ?
H11A C11 H11C . . 109.5 ?
H11B C11 H11C . . 109.5 ?
C3 C12 H12A . . 109.5 ?
C3 C12 H12B . . 109.5 ?
H12A C12 H12B . . 109.5 ?
C3 C12 H12C . . 109.5 ?
H12A C12 H12C . . 109.5 ?
H12B C12 H12C . . 109.5 ?
C10 N1 C7 . . 112.72(14) ?
C10 N1 C1 . . 124.29(14) ?
C7 N1 C1 . . 122.92(14) ?
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 C6 . 1.383(2) ?
C1 C2 . 1.390(2) ?
C1 N1 . 1.435(2) ?
C2 C3 . 1.402(2) ?
C2 C11 . 1.502(2) ?
C3 C4 . 1.384(3) ?
C3 C12 . 1.503(3) ?
C4 C5 . 1.372(3) ?
C4 H4 . 0.9300 ?
C5 C6 . 1.377(3) ?
C5 H5 . 0.9300 ?
C6 H6 . 0.9300 ?
C7 O1 . 1.203(2) ?
C7 N1 . 1.395(2) ?
C7 C8 . 1.503(3) ?
C8 C9 . 1.512(3) ?
C8 H8A . 0.9700 ?
C8 H8B . 0.9700 ?
C9 C10 . 1.498(3) ?
C9 H9A . 0.9700 ?
C9 H9B . 0.9700 ?
C10 O2 . 1.206(2) ?
C10 N1 . 1.389(2) ?
C11 H11A . 0.9600 ?
C11 H11B . 0.9600 ?
C11 H11C . 0.9600 ?
C12 H12A . 0.9600 ?
C12 H12B . 0.9600 ?
C12 H12C . 0.9600 ?
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 . . . . 3.0(2) ?
N1 C1 C2 C3 . . . . -176.40(15) ?
C6 C1 C2 C11 . . . . -175.79(16) ?
N1 C1 C2 C11 . . . . 4.8(2) ?
C1 C2 C3 C4 . . . . -2.4(2) ?
C11 C2 C3 C4 . . . . 176.39(17) ?
C1 C2 C3 C12 . . . . 177.13(18) ?
C11 C2 C3 C12 . . . . -4.1(3) ?
C2 C3 C4 C5 . . . . 0.2(3) ?
C12 C3 C4 C5 . . . . -179.3(2) ?
C3 C4 C5 C6 . . . . 1.5(3) ?
C4 C5 C6 C1 . . . . -0.9(3) ?
C2 C1 C6 C5 . . . . -1.4(3) ?
N1 C1 C6 C5 . . . . 178.08(16) ?
O1 C7 C8 C9 . . . . 174.0(2) ?
N1 C7 C8 C9 . . . . -5.7(2) ?
C7 C8 C9 C10 . . . . 3.9(2) ?
C8 C9 C10 O2 . . . . 178.99(19) ?
C8 C9 C10 N1 . . . . -0.8(2) ?
O2 C10 N1 C7 . . . . 177.23(18) ?
C9 C10 N1 C7 . . . . -2.9(2) ?
O2 C10 N1 C1 . . . . 0.2(3) ?
C9 C10 N1 C1 . . . . -179.96(16) ?
O1 C7 N1 C10 . . . . -174.22(17) ?
C8 C7 N1 C10 . . . . 5.5(2) ?
O1 C7 N1 C1 . . . . 2.9(3) ?
C8 C7 N1 C1 . . . . -177.41(15) ?
C6 C1 N1 C10 . . . . 67.5(2) ?
C2 C1 N1 C10 . . . . -113.08(19) ?
C6 C1 N1 C7 . . . . -109.27(19) ?
C2 C1 N1 C7 . . . . 70.2(2) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 23455669
