#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/48/2224848.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_2224848
loop_
_publ_author_name
'Gowda, B. Thimme'
'Foro, Sabine'
'Saraswathi, B. S.'
'Fuess, Hartmut'
_publ_section_title
;
 N-(3-Methylphenyl)succinamic acid
;
_journal_coeditor_code           BQ2189
_journal_issue                   2
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o394
_journal_paper_doi               10.1107/S1600536810001480
_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-(3-Methylphenyl)succinamic acid
;
_space_group_IT_number           56
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2ab 2ac'
_symmetry_space_group_name_H-M   'P c c n'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   12.0661(8)
_cell_length_b                   20.2200(10)
_cell_length_c                   8.9398(5)
_cell_measurement_reflns_used    4700
_cell_measurement_temperature    299(2)
_cell_measurement_theta_max      27.82
_cell_measurement_theta_min      2.48
_cell_volume                     2181.1(2)
_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 0.998
_diffrn_measured_fraction_theta_max 0.998
_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  0.0185
_diffrn_reflns_av_sigmaI/netI    0.0131
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            9274
_diffrn_reflns_theta_full        26.36
_diffrn_reflns_theta_max         26.36
_diffrn_reflns_theta_min         3.01
_diffrn_standards_decay_%        0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.092
_exptl_absorpt_correction_T_max  0.9800
_exptl_absorpt_correction_T_min  0.9605
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(CrysAlis RED; Oxford Diffraction, 2009)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.262
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       rod
_exptl_crystal_F_000             880
_exptl_crystal_size_max          0.44
_exptl_crystal_size_mid          0.34
_exptl_crystal_size_min          0.22
_refine_diff_density_max         0.175
_refine_diff_density_min         -0.212
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     167
_refine_ls_number_reflns         2228
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.052
_refine_ls_R_factor_all          0.0574
_refine_ls_R_factor_gt           0.0445
_refine_ls_shift/su_max          0.029
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0567P)²+0.6529P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1114
_refine_ls_wR_factor_ref         0.1207
_reflns_number_gt                1772
_reflns_number_total             2228
_reflns_threshold_expression     I>2sigma(I)
_cod_data_source_file            bq2189.cif
_cod_data_source_block           I
_cod_database_code               2224848
_cod_database_fobs_code          2224848
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y+1/2, z'
'x+1/2, -y, -z+1/2'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, y-1/2, -z'
'-x-1/2, y, z-1/2'
'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
O O1 0.60319(12) 0.30046(6) 0.00527(12) 0.0586(4) Uani d . 1 . .
O O2 0.51371(10) 0.44029(6) -0.12328(15) 0.0604(4) Uani d . 1 . .
O O3 0.64575(11) 0.48088(7) 0.02306(17) 0.0681(4) Uani d D 1 . .
H H3O 0.5948(14) 0.5046(10) 0.056(3) 0.082 Uiso d D 1 . .
N N1 0.55127(12) 0.24064(6) -0.19678(14) 0.0449(3) Uani d . 1 . .
H H1N 0.5651(14) 0.2366(9) -0.291(2) 0.054 Uiso d . 1 . .
C C1 0.49463(12) 0.18766(7) -0.12564(16) 0.0398(4) Uani d . 1 . .
C C2 0.42443(13) 0.19787(8) -0.00544(18) 0.0456(4) Uani d . 1 . .
H H2 0.4131(14) 0.2440(10) 0.0343(19) 0.055 Uiso d . 1 . .
C C3 0.37093(14) 0.14509(9) 0.0632(2) 0.0541(4) Uani d . 1 . .
C C4 0.38770(17) 0.08225(9) 0.0064(2) 0.0617(5) Uani d . 1 . .
H H4 0.3523(18) 0.0467(10) 0.052(2) 0.074 Uiso d . 1 . .
C C5 0.45474(17) 0.07211(9) -0.1154(2) 0.0627(5) Uani d . 1 . .
H H5 0.4654(17) 0.0287(11) -0.156(2) 0.075 Uiso d . 1 . .
C C6 0.50913(15) 0.12444(8) -0.1827(2) 0.0505(4) Uani d . 1 . .
H H6 0.5552(15) 0.1191(9) -0.270(2) 0.061 Uiso d . 1 . .
C C7 0.60056(13) 0.29228(7) -0.13003(16) 0.0401(4) Uani d . 1 . .
C C8 0.65448(16) 0.34114(8) -0.23546(18) 0.0470(4) Uani d . 1 . .
H H8A 0.5993(15) 0.3536(8) -0.311(2) 0.056 Uiso d . 1 . .
H H8B 0.7113(15) 0.3183(8) -0.285(2) 0.056 Uiso d . 1 . .
C C9 0.69866(15) 0.40119(9) -0.1542(2) 0.0514(4) Uani d . 1 . .
H H9A 0.7504(17) 0.3894(9) -0.078(2) 0.062 Uiso d . 1 . .
H H9B 0.7338(16) 0.4291(9) -0.223(2) 0.062 Uiso d . 1 . .
C C10 0.61046(13) 0.44199(7) -0.08284(18) 0.0449(4) Uani d . 1 . .
C C11 0.2978(2) 0.15574(12) 0.1975(3) 0.0901(8) Uani d . 1 . .
H H11A 0.2219 0.1582 0.1660 0.108 Uiso calc R 1 . .
H H11B 0.3183 0.1962 0.2462 0.108 Uiso calc R 1 . .
H H11C 0.3067 0.1195 0.2658 0.108 Uiso calc R 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
C10 O3 H3O . . 111.1(16) ?
C7 N1 C1 . . 126.93(12) ?
C7 N1 H1N . . 115.0(12) ?
C1 N1 H1N . . 117.2(12) ?
C2 C1 C6 . . 120.02(15) ?
C2 C1 N1 . . 121.97(13) ?
C6 C1 N1 . . 117.99(14) ?
C1 C2 C3 . . 120.83(15) ?
C1 C2 H2 . . 119.6(10) ?
C3 C2 H2 . . 119.5(10) ?
C4 C3 C2 . . 118.37(17) ?
C4 C3 C11 . . 120.66(17) ?
C2 C3 C11 . . 120.96(18) ?
C5 C4 C3 . . 121.00(17) ?
C5 C4 H4 . . 120.2(13) ?
C3 C4 H4 . . 118.8(13) ?
C4 C5 C6 . . 120.73(17) ?
C4 C5 H5 . . 120.9(13) ?
C6 C5 H5 . . 118.4(13) ?
C5 C6 C1 . . 119.01(17) ?
C5 C6 H6 . . 122.7(11) ?
C1 C6 H6 . . 118.2(11) ?
O1 C7 N1 . . 123.88(14) ?
O1 C7 C8 . . 121.17(14) ?
N1 C7 C8 . . 114.95(13) ?
C9 C8 C7 . . 112.13(13) ?
C9 C8 H8A . . 111.4(10) ?
C7 C8 H8A . . 107.8(10) ?
C9 C8 H8B . . 111.4(11) ?
C7 C8 H8B . . 106.8(11) ?
H8A C8 H8B . . 107.1(15) ?
C10 C9 C8 . . 113.49(15) ?
C10 C9 H9A . . 107.6(12) ?
C8 C9 H9A . . 111.9(11) ?
C10 C9 H9B . . 105.8(11) ?
C8 C9 H9B . . 109.0(11) ?
H9A C9 H9B . . 108.8(16) ?
O2 C10 O3 . . 122.97(15) ?
O2 C10 C9 . . 122.68(15) ?
O3 C10 C9 . . 114.33(15) ?
C3 C11 H11A . . 109.5 ?
C3 C11 H11B . . 109.5 ?
H11A C11 H11B . . 109.5 ?
C3 C11 H11C . . 109.5 ?
H11A C11 H11C . . 109.5 ?
H11B C11 H11C . . 109.5 ?
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
O1 C7 . 1.2212(17) ?
O2 C10 . 1.2226(19) ?
O3 C10 . 1.302(2) ?
O3 H3O . 0.832(10) ?
N1 C7 . 1.3416(19) ?
N1 C1 . 1.4210(19) ?
N1 H1N . 0.863(19) ?
C1 C2 . 1.384(2) ?
C1 C6 . 1.387(2) ?
C2 C3 . 1.390(2) ?
C2 H2 . 1.008(19) ?
C3 C4 . 1.383(3) ?
C3 C11 . 1.505(3) ?
C4 C5 . 1.372(3) ?
C4 H4 . 0.93(2) ?
C5 C6 . 1.383(3) ?
C5 H5 . 0.96(2) ?
C6 H6 . 0.96(2) ?
C7 C8 . 1.513(2) ?
C8 C9 . 1.512(2) ?
C8 H8A . 0.983(19) ?
C8 H8B . 0.940(19) ?
C9 C10 . 1.490(2) ?
C9 H9A . 0.95(2) ?
C9 H9B . 0.94(2) ?
C11 H11A . 0.9600 ?
C11 H11B . 0.9600 ?
C11 H11C . 0.9600 ?
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 8_565 0.863(19) 2.02(2) 2.8597(17) 163.5(16)
O3 H3O O2 5_665 0.832(10) 1.823(10) 2.6542(18) 177(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
C7 N1 C1 C2 . . . . 41.4(2) ?
C7 N1 C1 C6 . . . . -140.25(16) ?
C6 C1 C2 C3 . . . . 2.4(2) ?
N1 C1 C2 C3 . . . . -179.29(14) ?
C1 C2 C3 C4 . . . . -1.4(3) ?
C1 C2 C3 C11 . . . . 177.74(18) ?
C2 C3 C4 C5 . . . . -0.5(3) ?
C11 C3 C4 C5 . . . . -179.61(19) ?
C3 C4 C5 C6 . . . . 1.3(3) ?
C4 C5 C6 C1 . . . . -0.3(3) ?
C2 C1 C6 C5 . . . . -1.6(2) ?
N1 C1 C6 C5 . . . . -179.93(15) ?
C1 N1 C7 O1 . . . . 0.1(3) ?
C1 N1 C7 C8 . . . . -179.98(14) ?
O1 C7 C8 C9 . . . . -5.6(2) ?
N1 C7 C8 C9 . . . . 174.51(14) ?
C7 C8 C9 C10 . . . . -64.8(2) ?
C8 C9 C10 O2 . . . . -21.9(2) ?
C8 C9 C10 O3 . . . . 160.00(15) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 667291
