#------------------------------------------------------------------------------
#$Date: 2017-10-13 12:31:46 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201979 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/23/01/2230109.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_2230109
loop_
_publ_author_name
'He, Fei-Fei'
'Shi, Ya-Bin'
'Xia, Song'
'Wang, Hai-Bo'
_publ_section_title
;
 2-Methyl-4-(2-methylbenzamido)benzoic acid
;
_journal_coeditor_code           PK2306
_journal_issue                   5
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1050
_journal_paper_doi               10.1107/S160053681101110X
_journal_volume                  67
_journal_year                    2011
_chemical_formula_iupac          'C16 H15 N O3'
_chemical_formula_moiety         'C16 H15 N O3'
_chemical_formula_sum            'C16 H15 N O3'
_chemical_formula_weight         269.29
_chemical_melting_point          497
_chemical_name_systematic
;
2-Methyl-4-(2-methylbenzamido)benzoic acid
;
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/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                 125.50(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   23.318(9)
_cell_length_b                   10.230(2)
_cell_length_c                   13.901(3)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      13
_cell_measurement_theta_min      9
_cell_volume                     2699.6(16)
_computing_cell_refinement       'CAD-4 EXPRESS (Enraf--Nonius, 1989)'
_computing_data_collection       'CAD-4 EXPRESS (Enraf--Nonius, 1989)'
_computing_data_reduction        'XCAD4 (Harms & Wocadlo, 1995)'
_computing_molecular_graphics    'SHELXL97 (Sheldrick, 2008)'
_computing_publication_material  'PLATON (Spek, 2009)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_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           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0342
_diffrn_reflns_av_sigmaI/netI    0.0461
_diffrn_reflns_limit_h_max       28
_diffrn_reflns_limit_h_min       -28
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            4968
_diffrn_reflns_theta_full        25.41
_diffrn_reflns_theta_max         25.41
_diffrn_reflns_theta_min         2.15
_diffrn_standards_decay_%        1
_diffrn_standards_interval_time  120
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.092
_exptl_absorpt_correction_T_max  0.991
_exptl_absorpt_correction_T_min  0.982
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_process_details   '(North et al., 1968)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.325
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1136
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.187
_refine_diff_density_min         -0.179
_refine_ls_extinction_coef       0.0023(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.000
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     184
_refine_ls_number_reflns         2493
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.000
_refine_ls_R_factor_all          0.0811
_refine_ls_R_factor_gt           0.0467
_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)+(0.0750P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1186
_refine_ls_wR_factor_ref         0.1384
_reflns_number_gt                1641
_reflns_number_total             2493
_reflns_threshold_expression     >2σ(I)
_cod_data_source_file            pk2306.cif
_cod_data_source_block           I
_cod_original_cell_volume        2699.7(16)
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               2230109
_cod_database_fobs_code          2230109
loop_
_symmetry_equiv_pos_site_id
_symmetry_equiv_pos_as_xyz
1 x,y,z
2 -x,y,1/2-z
3 -x,-y,-z
4 x,-y,1/2+z
5 1/2+x,1/2+y,z
6 1/2-x,1/2+y,1/2-z
7 1/2-x,1/2-y,-z
8 1/2+x,1/2-y,1/2+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
N N 0.27879(10) 1.06074(17) 0.23814(17) 0.0431(5) Uani d . 1 . .
H H0A 0.2725 1.1380 0.2547 0.052 Uiso calc R 1 . .
O O1 0.25277(9) 0.84642(15) 0.23884(17) 0.0573(5) Uani d . 1 . .
C C1 0.09320(14) 0.8941(3) 0.0956(2) 0.0698(8) Uani d . 1 . .
H H1A 0.0432 0.8865 0.0559 0.105 Uiso calc R 1 . .
H H1B 0.1141 0.8086 0.1159 0.105 Uiso calc R 1 . .
H H1C 0.1026 0.9364 0.0445 0.105 Uiso calc R 1 . .
O O2 0.45652(10) 0.90523(16) 0.04728(17) 0.0639(6) Uani d . 1 . .
H H2A 0.4798 0.9040 0.0202 0.096 Uiso calc R 1 . .
C C2 0.12408(12) 0.9737(2) 0.2061(2) 0.0432(6) Uani d . 1 . .
O O3 0.46865(10) 1.11880(17) 0.03858(18) 0.0662(6) Uani d . 1 . .
C C3 0.08066(13) 1.0191(2) 0.2371(2) 0.0507(7) Uani d . 1 . .
H H3A 0.0328 1.0002 0.1884 0.061 Uiso calc R 1 . .
C C4 0.10675(14) 1.0914(2) 0.3382(2) 0.0496(7) Uani d . 1 . .
H H4A 0.0764 1.1214 0.3562 0.060 Uiso calc R 1 . .
C C5 0.17705(14) 1.1195(2) 0.4121(2) 0.0490(6) Uani d . 1 . .
H H5A 0.1949 1.1656 0.4818 0.059 Uiso calc R 1 . .
C C6 0.22118(12) 1.0787(2) 0.3823(2) 0.0440(6) Uani d . 1 . .
H H6A 0.2688 1.0997 0.4312 0.053 Uiso calc R 1 . .
C C7 0.19543(12) 1.0070(2) 0.2804(2) 0.0372(5) Uani d . 1 . .
C C8 0.24493(12) 0.9618(2) 0.2510(2) 0.0400(5) Uani d . 1 . .
C C9 0.32340(11) 1.0500(2) 0.2002(2) 0.0387(5) Uani d . 1 . .
C C10 0.32865(11) 1.1578(2) 0.1449(2) 0.0420(6) Uani d . 1 . .
H H10A 0.3043 1.2335 0.1373 0.050 Uiso calc R 1 . .
C C11 0.36888(12) 1.1568(2) 0.1007(2) 0.0409(6) Uani d . 1 . .
C C12 0.40456(11) 1.0408(2) 0.1123(2) 0.0404(6) Uani d . 1 . .
C C13 0.39995(12) 0.9348(2) 0.1700(2) 0.0458(6) Uani d . 1 . .
H H13A 0.4244 0.8589 0.1787 0.055 Uiso calc R 1 . .
C C14 0.36050(12) 0.9378(2) 0.2148(2) 0.0459(6) Uani d . 1 . .
H H14A 0.3589 0.8657 0.2540 0.055 Uiso calc R 1 . .
C C15 0.37002(14) 1.2772(2) 0.0391(2) 0.0555(7) Uani d . 1 . .
H H15A 0.3369 1.3400 0.0312 0.083 Uiso calc R 1 . .
H H15B 0.3574 1.2538 -0.0378 0.083 Uiso calc R 1 . .
H H15C 0.4164 1.3144 0.0848 0.083 Uiso calc R 1 . .
C C16 0.44573(12) 1.0256(2) 0.0627(2) 0.0452(6) 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
C8 N C9 . . 126.85(18) ?
C8 N H0A . . 116.6 ?
C9 N H0A . . 116.6 ?
C2 C1 H1A . . 109.5 ?
C2 C1 H1B . . 109.5 ?
H1A C1 H1B . . 109.5 ?
C2 C1 H1C . . 109.5 ?
H1A C1 H1C . . 109.5 ?
H1B C1 H1C . . 109.5 ?
C16 O2 H2A . . 109.5 ?
C3 C2 C7 . . 117.3(2) ?
C3 C2 C1 . . 119.7(2) ?
C7 C2 C1 . . 123.1(2) ?
C4 C3 C2 . . 121.7(2) ?
C4 C3 H3A . . 119.1 ?
C2 C3 H3A . . 119.1 ?
C5 C4 C3 . . 120.4(2) ?
C5 C4 H4A . . 119.8 ?
C3 C4 H4A . . 119.8 ?
C4 C5 C6 . . 119.3(2) ?
C4 C5 H5A . . 120.4 ?
C6 C5 H5A . . 120.4 ?
C5 C6 C7 . . 120.8(2) ?
C5 C6 H6A . . 119.6 ?
C7 C6 H6A . . 119.6 ?
C6 C7 C2 . . 120.50(19) ?
C6 C7 C8 . . 119.7(2) ?
C2 C7 C8 . . 119.8(2) ?
O1 C8 N . . 123.87(19) ?
O1 C8 C7 . . 122.33(19) ?
N C8 C7 . . 113.80(18) ?
C14 C9 C10 . . 119.50(19) ?
C14 C9 N . . 122.87(19) ?
C10 C9 N . . 117.63(18) ?
C11 C10 C9 . . 122.6(2) ?
C11 C10 H10A . . 118.7 ?
C9 C10 H10A . . 118.7 ?
C10 C11 C12 . . 117.56(19) ?
C10 C11 C15 . . 118.97(19) ?
C12 C11 C15 . . 123.43(18) ?
C13 C12 C11 . . 119.16(18) ?
C13 C12 C16 . . 118.4(2) ?
C11 C12 C16 . . 122.4(2) ?
C14 C13 C12 . . 122.6(2) ?
C14 C13 H13A . . 118.7 ?
C12 C13 H13A . . 118.7 ?
C13 C14 C9 . . 118.5(2) ?
C13 C14 H14A . . 120.7 ?
C9 C14 H14A . . 120.7 ?
C11 C15 H15A . . 109.5 ?
C11 C15 H15B . . 109.5 ?
H15A C15 H15B . . 109.5 ?
C11 C15 H15C . . 109.5 ?
H15A C15 H15C . . 109.5 ?
H15B C15 H15C . . 109.5 ?
O3 C16 O2 . . 122.23(19) ?
O3 C16 C12 . . 123.2(2) ?
O2 C16 C12 . . 114.6(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
N C8 . 1.357(3) ?
N C9 . 1.417(3) ?
N H0A . 0.8600 ?
O1 C8 . 1.221(3) ?
C1 C2 . 1.501(3) ?
C1 H1A . 0.9600 ?
C1 H1B . 0.9600 ?
C1 H1C . 0.9600 ?
O2 C16 . 1.300(3) ?
O2 H2A . 0.8200 ?
C2 C3 . 1.391(3) ?
C2 C7 . 1.398(3) ?
O3 C16 . 1.230(3) ?
C3 C4 . 1.378(4) ?
C3 H3A . 0.9300 ?
C4 C5 . 1.367(4) ?
C4 H4A . 0.9300 ?
C5 C6 . 1.378(3) ?
C5 H5A . 0.9300 ?
C6 C7 . 1.386(3) ?
C6 H6A . 0.9300 ?
C7 C8 . 1.503(3) ?
C9 C14 . 1.380(3) ?
C9 C10 . 1.389(3) ?
C10 C11 . 1.389(3) ?
C10 H10A . 0.9300 ?
C11 C12 . 1.404(3) ?
C11 C15 . 1.509(3) ?
C12 C13 . 1.388(3) ?
C12 C16 . 1.481(3) ?
C13 C14 . 1.379(3) ?
C13 H13A . 0.9300 ?
C14 H14A . 0.9300 ?
C15 H15A . 0.9600 ?
C15 H15B . 0.9600 ?
C15 H15C . 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
_geom_hbond_publ_flag
N H0A O1 6_555 0.86 2.23 3.076(3) 169 yes
O2 H2A O3 3_675 0.82 1.82 2.636(4) 174 yes
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 C2 C3 C4 . . . . -1.5(3) ?
C1 C2 C3 C4 . . . . 179.4(2) ?
C2 C3 C4 C5 . . . . -0.7(4) ?
C3 C4 C5 C6 . . . . 2.4(4) ?
C4 C5 C6 C7 . . . . -1.8(3) ?
C5 C6 C7 C2 . . . . -0.5(3) ?
C5 C6 C7 C8 . . . . -179.0(2) ?
C3 C2 C7 C6 . . . . 2.1(3) ?
C1 C2 C7 C6 . . . . -178.8(2) ?
C3 C2 C7 C8 . . . . -179.5(2) ?
C1 C2 C7 C8 . . . . -0.4(3) ?
C9 N C8 O1 . . . . 5.4(4) ?
C9 N C8 C7 . . . . -173.8(2) ?
C6 C7 C8 O1 . . . . 121.0(3) ?
C2 C7 C8 O1 . . . . -57.5(3) ?
C6 C7 C8 N . . . . -59.8(3) ?
C2 C7 C8 N . . . . 121.7(2) ?
C8 N C9 C14 . . . . -26.4(4) ?
C8 N C9 C10 . . . . 152.9(2) ?
C14 C9 C10 C11 . . . . 1.5(3) ?
N C9 C10 C11 . . . . -177.8(2) ?
C9 C10 C11 C12 . . . . 0.7(3) ?
C9 C10 C11 C15 . . . . 178.4(2) ?
C10 C11 C12 C13 . . . . -2.0(3) ?
C15 C11 C12 C13 . . . . -179.6(2) ?
C10 C11 C12 C16 . . . . 176.5(2) ?
C15 C11 C12 C16 . . . . -1.2(4) ?
C11 C12 C13 C14 . . . . 1.2(4) ?
C16 C12 C13 C14 . . . . -177.3(2) ?
C12 C13 C14 C9 . . . . 0.9(4) ?
C10 C9 C14 C13 . . . . -2.2(4) ?
N C9 C14 C13 . . . . 177.0(2) ?
C13 C12 C16 O3 . . . . -160.2(2) ?
C11 C12 C16 O3 . . . . 21.4(4) ?
C13 C12 C16 O2 . . . . 19.2(3) ?
C11 C12 C16 O2 . . . . -159.2(2) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 24541601
