#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/12/2221207.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_2221207
loop_
_publ_author_name
'Gowda, B. Thimme'
'Foro, Sabine'
'Saraswathi, B. S.'
'Terao, Hiromitsu'
'Fuess, Hartmut'
_publ_section_title
;
 N-(2,6-Dimethylphenyl)succinamic acid
;
_journal_coeditor_code           TK2369
_journal_issue                   3
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o466
_journal_paper_doi               10.1107/S1600536809003833
_journal_volume                  65
_journal_year                    2009
_chemical_formula_moiety         'C12 H15 N O3'
_chemical_formula_sum            'C12 H15 N O3'
_chemical_formula_weight         221.25
_chemical_name_common
'N-(2,6-Dimethylphenyl)succinamic acid'
_chemical_name_systematic
;
3-[(2,6-dimethylphenyl)aminocarbonyl]propionic acid
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 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
_cell_angle_beta                 111.160(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.9633(8)
_cell_length_b                   19.889(2)
_cell_length_c                   7.9822(8)
_cell_measurement_reflns_used    3013
_cell_measurement_temperature    299(2)
_cell_measurement_theta_max      28.0
_cell_measurement_theta_min      2.7
_cell_volume                     1179.0(2)
_computing_cell_refinement
;
CrysAlis RED (Oxford Diffraction, 2007)
;
_computing_data_collection
;
CrysAlis CCD (Oxford Diffraction, 2004)
;
_computing_data_reduction
;
CrysAlis RED (Oxford Diffraction, 2004)
;
_computing_molecular_graphics    'PLATON (Spek, 2003)'
_computing_publication_material  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type
;
Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector
;
_diffrn_measurement_method
;
Rotation method data acquisition using ω and φ
;
_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  0.017
_diffrn_reflns_av_sigmaI/netI    0.016
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            6777
_diffrn_reflns_theta_full        26.4
_diffrn_reflns_theta_max         26.4
_diffrn_reflns_theta_min         2.9
_diffrn_standards_decay_%        0
_exptl_absorpt_coefficient_mu    0.090
_exptl_absorpt_correction_T_max  0.966
_exptl_absorpt_correction_T_min  0.958
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(CrysAlis RED; Oxford Diffraction, 2007)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.246
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             472
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.48
_exptl_crystal_size_min          0.40
_refine_diff_density_max         0.19
_refine_diff_density_min         -0.17
_refine_ls_extinction_coef       0.017(4)
_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   1.051
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     154
_refine_ls_number_reflns         2391
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.05
_refine_ls_R_factor_all          0.058
_refine_ls_R_factor_gt           0.043
_refine_ls_shift/su_max          0.03
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0691P)²+0.3248P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.120
_refine_ls_wR_factor_ref         0.135
_reflns_number_gt                1826
_reflns_number_total             2391
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            tk2369.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               2221207
_cod_database_fobs_code          2221207
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -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 0.12966(19) 0.18528(8) 0.03678(19) 0.0379(4) Uani d . 1 . .
C C2 0.0916(2) 0.11993(8) 0.0772(2) 0.0480(4) Uani d . 1 . .
C C3 0.2273(3) 0.07205(10) 0.1098(3) 0.0688(6) Uani d . 1 . .
H H3 0.2062 0.0282 0.1376 0.083 Uiso calc R 1 . .
C C4 0.3924(3) 0.08854(14) 0.1016(3) 0.0799(8) Uani d . 1 . .
H H4 0.4816 0.0559 0.1241 0.096 Uiso calc R 1 . .
C C5 0.4251(3) 0.15276(13) 0.0604(3) 0.0693(6) Uani d . 1 . .
H H5 0.5369 0.1632 0.0552 0.083 Uiso calc R 1 . .
C C6 0.2949(2) 0.20310(10) 0.0260(2) 0.0483(4) Uani d . 1 . .
C C7 0.00487(18) 0.28812(7) 0.11169(19) 0.0353(3) Uani d . 1 . .
C C8 -0.1610(2) 0.33204(8) 0.0593(2) 0.0434(4) Uani d . 1 . .
H H8A -0.2293 0.3264 -0.0679 0.052 Uiso calc R 1 . .
H H8B -0.2363 0.3174 0.1245 0.052 Uiso calc R 1 . .
C C9 -0.1168(2) 0.40548(8) 0.0976(2) 0.0467(4) Uani d . 1 . .
H H9A -0.0409 0.4109 0.2229 0.056 Uiso calc R 1 . .
H H9B -0.0499 0.4212 0.0250 0.056 Uiso calc R 1 . .
C C10 -0.2830(2) 0.44735(8) 0.0582(2) 0.0473(4) Uani d . 1 . .
C C11 -0.0877(3) 0.10257(10) 0.0884(3) 0.0637(5) Uani d . 1 . .
H H11A -0.1803 0.1074 -0.0280 0.076 Uiso calc R 1 . .
H H11B -0.1120 0.1323 0.1717 0.076 Uiso calc R 1 . .
H H11C -0.0854 0.0570 0.1287 0.076 Uiso calc R 1 . .
C C12 0.3334(3) 0.27264(12) -0.0218(3) 0.0662(6) Uani d . 1 . .
H H12A 0.3733 0.3001 0.0843 0.079 Uiso calc R 1 . .
H H12B 0.2258 0.2916 -0.1077 0.079 Uiso calc R 1 . .
H H12C 0.4256 0.2709 -0.0727 0.079 Uiso calc R 1 . .
N N1 -0.00837(16) 0.23498(6) 0.00415(17) 0.0368(3) Uani d . 1 . .
H H1N -0.111(2) 0.2276(9) -0.079(2) 0.044 Uiso d . 1 . .
O O1 0.13819(13) 0.30009(6) 0.24524(15) 0.0469(3) Uani d . 1 . .
O O2 -0.25948(19) 0.51129(6) 0.0379(2) 0.0750(5) Uani d . 1 . .
H H2O -0.363(4) 0.5325(13) 0.012(3) 0.090 Uiso d . 1 . .
O O3 -0.42763(16) 0.42371(6) 0.0464(2) 0.0714(5) 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
C6 C1 C2 . . 122.55(15) ?
C6 C1 N1 . . 119.54(15) ?
C2 C1 N1 . . 117.91(14) ?
C3 C2 C1 . . 117.43(18) ?
C3 C2 C11 . . 121.43(18) ?
C1 C2 C11 . . 121.12(15) ?
C4 C3 C2 . . 121.1(2) ?
C4 C3 H3 . . 119.4 ?
C2 C3 H3 . . 119.4 ?
C5 C4 C3 . . 120.05(18) ?
C5 C4 H4 . . 120.0 ?
C3 C4 H4 . . 120.0 ?
C4 C5 C6 . . 121.7(2) ?
C4 C5 H5 . . 119.1 ?
C6 C5 H5 . . 119.1 ?
C1 C6 C5 . . 117.12(19) ?
C1 C6 C12 . . 122.35(15) ?
C5 C6 C12 . . 120.53(18) ?
O1 C7 N1 . . 123.55(13) ?
O1 C7 C8 . . 121.63(13) ?
N1 C7 C8 . . 114.79(12) ?
C9 C8 C7 . . 112.76(12) ?
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 . . 111.83(13) ?
C10 C9 H9A . . 109.3 ?
C8 C9 H9A . . 109.3 ?
C10 C9 H9B . . 109.3 ?
C8 C9 H9B . . 109.3 ?
H9A C9 H9B . . 107.9 ?
O3 C10 O2 . . 122.82(15) ?
O3 C10 C9 . . 122.82(15) ?
O2 C10 C9 . . 114.37(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 ?
C6 C12 H12A . . 109.5 ?
C6 C12 H12B . . 109.5 ?
H12A C12 H12B . . 109.5 ?
C6 C12 H12C . . 109.5 ?
H12A C12 H12C . . 109.5 ?
H12B C12 H12C . . 109.5 ?
C7 N1 C1 . . 123.37(12) ?
C7 N1 H1N . . 117.7(12) ?
C1 N1 H1N . . 118.3(12) ?
C10 O2 H2O . . 109.4(16) ?
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 . 1.395(2) ?
C1 C2 . 1.398(2) ?
C1 N1 . 1.4306(18) ?
C2 C3 . 1.393(2) ?
C2 C11 . 1.503(3) ?
C3 C4 . 1.379(3) ?
C3 H3 . 0.9300 ?
C4 C5 . 1.367(4) ?
C4 H4 . 0.9300 ?
C5 C6 . 1.395(3) ?
C5 H5 . 0.9300 ?
C6 C12 . 1.495(3) ?
C7 O1 . 1.2260(17) ?
C7 N1 . 1.3415(19) ?
C7 C8 . 1.5115(19) ?
C8 C9 . 1.508(2) ?
C8 H8A . 0.9700 ?
C8 H8B . 0.9700 ?
C9 C10 . 1.498(2) ?
C9 H9A . 0.9700 ?
C9 H9B . 0.9700 ?
C10 O3 . 1.216(2) ?
C10 O2 . 1.304(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 ?
N1 H1N . 0.859(18) ?
O2 H2O . 0.88(3) ?
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 0.859(18) 2.059(19) 2.9120(16) 171.8(17)
O2 H2O O3 3_465 0.88(3) 1.79(3) 2.6686(18) 178(3)
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 . . . . 0.9(2) ?
N1 C1 C2 C3 . . . . -179.61(14) ?
C6 C1 C2 C11 . . . . 179.75(15) ?
N1 C1 C2 C11 . . . . -0.8(2) ?
C1 C2 C3 C4 . . . . -0.3(3) ?
C11 C2 C3 C4 . . . . -179.12(18) ?
C2 C3 C4 C5 . . . . -0.2(3) ?
C3 C4 C5 C6 . . . . 0.1(3) ?
C2 C1 C6 C5 . . . . -1.0(2) ?
N1 C1 C6 C5 . . . . 179.54(14) ?
C2 C1 C6 C12 . . . . 178.40(16) ?
N1 C1 C6 C12 . . . . -1.0(2) ?
C4 C5 C6 C1 . . . . 0.5(3) ?
C4 C5 C6 C12 . . . . -178.95(19) ?
O1 C7 C8 C9 . . . . 36.3(2) ?
N1 C7 C8 C9 . . . . -145.43(15) ?
C7 C8 C9 C10 . . . . -175.54(14) ?
C8 C9 C10 O3 . . . . 19.1(3) ?
C8 C9 C10 O2 . . . . -161.05(17) ?
O1 C7 N1 C1 . . . . 2.0(2) ?
C8 C7 N1 C1 . . . . -176.22(14) ?
C6 C1 N1 C7 . . . . -66.5(2) ?
C2 C1 N1 C7 . . . . 114.05(17) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 299821
