#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/56/2225657.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_2225657
loop_
_publ_author_name
'Gowda, B. Thimme'
'Foro, Sabine'
'Saraswathi, B. S.'
'Fuess, Hartmut'
_publ_section_title
;
 N-(2-Methylphenyl)succinamic acid
;
_journal_coeditor_code           LX2138
_journal_issue                   4
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o908
_journal_paper_doi               10.1107/S1600536810010329
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C11 H13 N O3'
_chemical_formula_moiety         'C11 H13 N O3'
_chemical_formula_sum            'C11 H13 N O3'
_chemical_formula_weight         207.22
_chemical_name_systematic
;
N-(2-Methylphenyl)succinamic acid
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                86.20(2)
_cell_angle_beta                 83.020(10)
_cell_angle_gamma                88.45(2)
_cell_formula_units_Z            2
_cell_length_a                   4.7756(9)
_cell_length_b                   6.1854(9)
_cell_length_c                   18.275(3)
_cell_measurement_reflns_used    1326
_cell_measurement_temperature    299(2)
_cell_measurement_theta_max      27.71
_cell_measurement_theta_min      3.30
_cell_volume                     534.55(16)
_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) and DIAMOND (Brandenburg, 1998)'
_computing_publication_material  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      299(2)
_diffrn_detector_area_resol_mean 10.0
_diffrn_measured_fraction_theta_full 0.986
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measurement_device_type  'Oxford Diffraction Xcalibur'
_diffrn_measurement_method       'φ and ω 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  0.0095
_diffrn_reflns_av_sigmaI/netI    0.0177
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            2928
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         3.30
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.094
_exptl_absorpt_correction_T_max  0.9944
_exptl_absorpt_correction_T_min  0.9633
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(CrysAlis RED; Oxford Diffraction, 2009)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.287
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             220
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.331
_refine_diff_density_min         -0.311
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.101
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     143
_refine_ls_number_reflns         1873
_refine_ls_number_restraints     13
_refine_ls_restrained_S_all      1.226
_refine_ls_R_factor_all          0.0826
_refine_ls_R_factor_gt           0.0601
_refine_ls_shift/esd_max         0.000
_refine_ls_shift/su_max_lt       0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0463P)²+0.4371P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1332
_refine_ls_wR_factor_ref         0.1492
_reflns_number_gt                1426
_reflns_number_total             1873
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            lx2138.cif
_cod_data_source_block           I
_cod_original_cell_volume        534.55(15)
_cod_database_code               2225657
_cod_database_fobs_code          2225657
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
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 0.0519(5) -0.0093(4) 0.80080(16) 0.0415(7) Uani d . 1 . .
C C2 -0.0898(6) -0.0197(5) 0.87207(16) 0.0445(7) Uani d . 1 . .
C C3 -0.0147(7) -0.1877(5) 0.92098(19) 0.0577(9) Uani d . 1 . .
H H3 -0.1085 -0.1994 0.9687 0.069 Uiso calc R 1 . .
C C4 0.1940(8) -0.3363(5) 0.9006(2) 0.0685(10) Uani d . 1 . .
H H4 0.2402 -0.4465 0.9344 0.082 Uiso calc R 1 . .
C C5 0.3342(8) -0.3227(5) 0.8307(2) 0.0648(10) Uani d . 1 . .
H H5 0.4767 -0.4227 0.8170 0.078 Uiso calc R 1 . .
C C6 0.2631(7) -0.1594(5) 0.78027(19) 0.0538(8) Uani d . 1 . .
H H6 0.3572 -0.1504 0.7326 0.065 Uiso calc R 1 . .
C C7 0.1616(5) 0.2852(5) 0.70612(15) 0.0424(7) Uani d . 1 . .
C C8 0.0310(5) 0.4576(5) 0.65761(16) 0.0476(8) Uani d . 1 . .
H H8A -0.1193 0.3942 0.6354 0.057 Uiso calc R 1 . .
H H8B -0.0521 0.5710 0.6880 0.057 Uiso calc R 1 . .
C C9 0.2412(6) 0.5563(5) 0.59738(17) 0.0504(8) Uani d . 1 . .
H H9A 0.4044 0.6001 0.6192 0.060 Uiso calc R 1 . .
H H9B 0.3040 0.4467 0.5632 0.060 Uiso calc R 1 . .
C C10 0.1294(6) 0.7472(5) 0.55537(16) 0.0474(8) Uani d . 1 . .
C C11 -0.3113(7) 0.1471(6) 0.89617(19) 0.0583(9) Uani d . 1 . .
H H11A -0.2352 0.2894 0.8858 0.087 Uiso calc R 1 . .
H H11B -0.3683 0.1241 0.9483 0.087 Uiso calc R 1 . .
H H11C -0.4716 0.1340 0.8699 0.087 Uiso calc R 1 . .
N N1 -0.0225(5) 0.1572(4) 0.74871(14) 0.0440(6) Uani d . 1 . .
H H1N -0.189(7) 0.181(6) 0.7458(19) 0.066 Uiso d . 1 . .
O O1 0.4164(4) 0.2708(4) 0.70798(13) 0.0665(8) Uani d . 1 . .
O O2 -0.0821(6) 0.8479(5) 0.57850(15) 0.0915(10) Uani d U 1 . .
O O3 0.2743(7) 0.8021(5) 0.49406(15) 0.0937(10) Uani d DU 1 . .
H H3O 0.201(10) 0.914(6) 0.474(3) 0.141 Uiso d 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
C6 C1 C2 . . 120.7(3) ?
C6 C1 N1 . . 120.0(3) ?
C2 C1 N1 . . 119.3(3) ?
C1 C2 C3 . . 117.5(3) ?
C1 C2 C11 . . 121.4(2) ?
C3 C2 C11 . . 121.1(3) ?
C4 C3 C2 . . 121.7(3) ?
C4 C3 H3 . . 119.1 ?
C2 C3 H3 . . 119.1 ?
C5 C4 C3 . . 120.2(3) ?
C5 C4 H4 . . 119.9 ?
C3 C4 H4 . . 119.9 ?
C4 C5 C6 . . 119.7(3) ?
C4 C5 H5 . . 120.1 ?
C6 C5 H5 . . 120.1 ?
C5 C6 C1 . . 120.1(3) ?
C5 C6 H6 . . 119.9 ?
C1 C6 H6 . . 119.9 ?
O1 C7 N1 . . 123.0(2) ?
O1 C7 C8 . . 121.8(2) ?
N1 C7 C8 . . 115.1(2) ?
C9 C8 C7 . . 112.8(2) ?
C9 C8 H8A . . 109.0 ?
C7 C8 H8A . . 109.0 ?
C9 C8 H8B . . 109.0 ?
C7 C8 H8B . . 109.0 ?
H8A C8 H8B . . 107.8 ?
C10 C9 C8 . . 114.1(2) ?
C10 C9 H9A . . 108.7 ?
C8 C9 H9A . . 108.7 ?
C10 C9 H9B . . 108.7 ?
C8 C9 H9B . . 108.7 ?
H9A C9 H9B . . 107.6 ?
O2 C10 O3 . . 122.0(3) ?
O2 C10 C9 . . 122.6(3) ?
O3 C10 C9 . . 115.4(3) ?
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 ?
C7 N1 C1 . . 124.8(2) ?
C7 N1 H1N . . 117(3) ?
C1 N1 H1N . . 118(3) ?
C10 O3 H3O . . 110(4) ?
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 . 1.387(4) ?
C1 C2 . 1.391(4) ?
C1 N1 . 1.423(3) ?
C2 C3 . 1.393(4) ?
C2 C11 . 1.505(4) ?
C3 C4 . 1.372(5) ?
C3 H3 . 0.9300 ?
C4 C5 . 1.367(5) ?
C4 H4 . 0.9300 ?
C5 C6 . 1.385(5) ?
C5 H5 . 0.9300 ?
C6 H6 . 0.9300 ?
C7 O1 . 1.222(3) ?
C7 N1 . 1.340(4) ?
C7 C8 . 1.512(4) ?
C8 C9 . 1.506(4) ?
C8 H8A . 0.9700 ?
C8 H8B . 0.9700 ?
C9 C10 . 1.488(4) ?
C9 H9A . 0.9700 ?
C9 H9B . 0.9700 ?
C10 O2 . 1.218(4) ?
C10 O3 . 1.274(4) ?
C11 H11A . 0.9600 ?
C11 H11B . 0.9600 ?
C11 H11C . 0.9600 ?
N1 H1N . 0.81(4) ?
O3 H3O . 0.85(2) ?
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 1_455 0.81(4) 2.13(4) 2.922(3) 164(3)
O3 H3O O2 2_576 0.85(2) 1.82(2) 2.664(3) 173(5)
C11 H11A Cg 1_565 0.96 2.81 3.596(4) 139.2
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 . . . . -1.1(4) ?
N1 C1 C2 C3 . . . . 178.7(3) ?
C6 C1 C2 C11 . . . . 177.5(3) ?
N1 C1 C2 C11 . . . . -2.7(4) ?
C1 C2 C3 C4 . . . . 1.0(5) ?
C11 C2 C3 C4 . . . . -177.6(3) ?
C2 C3 C4 C5 . . . . -0.2(5) ?
C3 C4 C5 C6 . . . . -0.6(6) ?
C4 C5 C6 C1 . . . . 0.5(5) ?
C2 C1 C6 C5 . . . . 0.4(5) ?
N1 C1 C6 C5 . . . . -179.4(3) ?
O1 C7 C8 C9 . . . . 17.9(5) ?
N1 C7 C8 C9 . . . . -164.8(3) ?
C7 C8 C9 C10 . . . . -171.8(3) ?
C8 C9 C10 O2 . . . . 17.7(5) ?
C8 C9 C10 O3 . . . . -164.0(3) ?
O1 C7 N1 C1 . . . . 0.0(5) ?
C8 C7 N1 C1 . . . . -177.2(3) ?
C6 C1 N1 C7 . . . . -48.9(4) ?
C2 C1 N1 C7 . . . . 131.2(3) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 604161
