#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/67/2226705.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_2226705
loop_
_publ_author_name
'Gowda, B. Thimme'
'Tokarčík, Miroslav'
'Rodrigues, Vinola Z.'
'Kožíšek, Jozef'
'Fuess, Hartmut'
_publ_section_title
;
 3-Methyl-N-(2-methylphenyl)benzamide
;
_journal_coeditor_code           VM2033
_journal_issue                   7
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1849
_journal_paper_doi               10.1107/S1600536810024578
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C15 H15 N O'
_chemical_formula_moiety         'C15 H15 N O'
_chemical_formula_sum            'C15 H15 N O'
_chemical_formula_weight         225.28
_chemical_name_systematic
;
3-Methyl-N-(2-methylphenyl)benzamide
;
_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           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                90
_cell_angle_beta                 116.512(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.1896(3)
_cell_length_b                   4.95027(14)
_cell_length_c                   24.1164(5)
_cell_measurement_reflns_used    6151
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      29.4435
_cell_measurement_theta_min      3.3902
_cell_volume                     1195.37(6)
_computing_cell_refinement
;
CrysAlis Pro (Oxford Diffraction, 2009)
;
_computing_data_collection
;
CrysAlis Pro (Oxford Diffraction, 2009)
;
_computing_data_reduction
;
CrysAlis Pro (Oxford Diffraction, 2009)
;
_computing_molecular_graphics
;
ORTEP-3 (Farrugia, 1997) and DIAMOND (Brandenburg, 2002)
;
_computing_publication_material
;
SHELXL97 (Sheldrick, 2008), PLATON (Spek, 2009) and WinGX
(Farrugia, 1999)
;
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      295(2)
_diffrn_detector_area_resol_mean 10.434
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Oxford Diffraction Gemini R CCD'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0356
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            13694
_diffrn_reflns_theta_full        25.09
_diffrn_reflns_theta_max         25.09
_diffrn_reflns_theta_min         2.07
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.078
_exptl_absorpt_correction_T_max  0.993
_exptl_absorpt_correction_T_min  0.954
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(CrysAlis Pro; Oxford Diffraction, 2009)
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.252
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       rod
_exptl_crystal_F_000             480
_exptl_crystal_size_max          0.55
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.175
_refine_diff_density_min         -0.16
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.017
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     156
_refine_ls_number_reflns         2124
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.017
_refine_ls_R_factor_all          0.0572
_refine_ls_R_factor_gt           0.0418
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0850P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1206
_refine_ls_wR_factor_ref         0.1262
_reflns_number_gt                1553
_reflns_number_total             2124
_reflns_threshold_expression     I>2sigma(I)
_cod_data_source_file            vm2033.cif
_cod_data_source_block           I
_cod_original_cell_volume        1195.37(5)
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2226705
_cod_database_fobs_code          2226705
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 0.60977(14) 0.5878(3) 0.45102(7) 0.0380(4) Uani d . 1 . .
C C2 0.62846(15) 0.3929(3) 0.41406(7) 0.0400(4) Uani d . 1 . .
H H2 0.7127 0.3169 0.4269 0.048 Uiso calc R 1 . .
C C3 0.52474(15) 0.3091(3) 0.35868(7) 0.0421(4) Uani d . 1 . .
C C4 0.40013(16) 0.4216(3) 0.34128(8) 0.0485(4) Uani d . 1 . .
H H4 0.3288 0.3659 0.3046 0.058 Uiso calc R 1 . .
C C5 0.37946(16) 0.6155(3) 0.37739(8) 0.0496(4) Uani d . 1 . .
H H5 0.2947 0.6884 0.3649 0.06 Uiso calc R 1 . .
C C6 0.48384(15) 0.7010(3) 0.43174(7) 0.0445(4) Uani d . 1 . .
H H6 0.4701 0.8342 0.4555 0.053 Uiso calc R 1 . .
C C7 0.72176(14) 0.6863(3) 0.50986(7) 0.0386(4) Uani d U 1 . .
C C8 0.92671(14) 0.5441(3) 0.60094(7) 0.0366(4) Uani d . 1 . .
C C9 1.04382(15) 0.4018(3) 0.61249(7) 0.0398(4) Uani d . 1 . .
C C10 1.15481(17) 0.4475(3) 0.66806(8) 0.0529(5) Uani d . 1 . .
H H10 1.233 0.353 0.6767 0.064 Uiso calc R 1 . .
C C11 1.15358(18) 0.6281(4) 0.71109(8) 0.0587(5) Uani d . 1 . .
H H11 1.2302 0.6558 0.748 0.07 Uiso calc R 1 . .
C C12 1.03848(18) 0.7672(3) 0.69924(8) 0.0543(5) Uani d . 1 . .
H H12 1.0372 0.89 0.7282 0.065 Uiso calc R 1 . .
C C13 0.92508(16) 0.7255(3) 0.64467(7) 0.0453(4) Uani d . 1 . .
H H13 0.8471 0.8189 0.637 0.054 Uiso calc R 1 . .
C C14 0.54820(18) 0.1002(3) 0.31908(8) 0.0551(5) Uani d . 1 . .
H H14A 0.6314 0.1368 0.318 0.083 Uiso calc R 1 . .
H H14B 0.4767 0.107 0.2778 0.083 Uiso calc R 1 . .
H H14C 0.5514 -0.0761 0.3363 0.083 Uiso calc R 1 . .
C C15 1.04971(16) 0.2057(3) 0.56617(8) 0.0499(4) Uani d . 1 . .
H H15A 1.0146 0.2898 0.5261 0.075 Uiso calc R 1 . .
H H15B 0.9975 0.0487 0.5641 0.075 Uiso calc R 1 . .
H H15C 1.1407 0.1533 0.5787 0.075 Uiso calc R 1 . .
N N1 0.81081(12) 0.4968(2) 0.54447(6) 0.0394(3) Uani d . 1 . .
H H1N 0.796 0.3332 0.5311 0.047 Uiso calc R 1 . .
O O1 0.73096(11) 0.92511(18) 0.52470(5) 0.0555(4) Uani d U 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 0 '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 0.006 '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 . . 119.03(14) ?
C6 C1 C7 . . 118.77(13) ?
C2 C1 C7 . . 122.16(13) ?
C3 C2 C1 . . 121.63(14) ?
C3 C2 H2 . . 119.2 ?
C1 C2 H2 . . 119.2 ?
C4 C3 C2 . . 118.03(14) ?
C4 C3 C14 . . 121.44(14) ?
C2 C3 C14 . . 120.54(14) ?
C3 C4 C5 . . 121.22(15) ?
C3 C4 H4 . . 119.4 ?
C5 C4 H4 . . 119.4 ?
C6 C5 C4 . . 120.25(15) ?
C6 C5 H5 . . 119.9 ?
C4 C5 H5 . . 119.9 ?
C5 C6 C1 . . 119.82(15) ?
C5 C6 H6 . . 120.1 ?
C1 C6 H6 . . 120.1 ?
O1 C7 N1 . . 123.11(14) ?
O1 C7 C1 . . 121.14(13) ?
N1 C7 C1 . . 115.75(12) ?
C13 C8 C9 . . 120.07(14) ?
C13 C8 N1 . . 121.22(13) ?
C9 C8 N1 . . 118.71(13) ?
C10 C9 C8 . . 117.84(14) ?
C10 C9 C15 . . 120.56(14) ?
C8 C9 C15 . . 121.60(14) ?
C11 C10 C9 . . 122.13(16) ?
C11 C10 H10 . . 118.9 ?
C9 C10 H10 . . 118.9 ?
C12 C11 C10 . . 119.58(16) ?
C12 C11 H11 . . 120.2 ?
C10 C11 H11 . . 120.2 ?
C11 C12 C13 . . 120.16(15) ?
C11 C12 H12 . . 119.9 ?
C13 C12 H12 . . 119.9 ?
C12 C13 C8 . . 120.21(15) ?
C12 C13 H13 . . 119.9 ?
C8 C13 H13 . . 119.9 ?
C3 C14 H14A . . 109.5 ?
C3 C14 H14B . . 109.5 ?
H14A C14 H14B . . 109.5 ?
C3 C14 H14C . . 109.5 ?
H14A C14 H14C . . 109.5 ?
H14B C14 H14C . . 109.5 ?
C9 C15 H15A . . 109.5 ?
C9 C15 H15B . . 109.5 ?
H15A C15 H15B . . 109.5 ?
C9 C15 H15C . . 109.5 ?
H15A C15 H15C . . 109.5 ?
H15B C15 H15C . . 109.5 ?
C7 N1 C8 . . 125.73(12) ?
C7 N1 H1N . . 117.1 ?
C8 N1 H1N . . 117.1 ?
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 . 1.390(2) ?
C1 C2 . 1.391(2) ?
C1 C7 . 1.495(2) ?
C2 C3 . 1.385(2) ?
C2 H2 . 0.93 ?
C3 C4 . 1.381(2) ?
C3 C14 . 1.508(2) ?
C4 C5 . 1.383(2) ?
C4 H4 . 0.93 ?
C5 C6 . 1.376(2) ?
C5 H5 . 0.93 ?
C6 H6 . 0.93 ?
C7 O1 . 1.2262(16) ?
C7 N1 . 1.3517(18) ?
C8 C13 . 1.391(2) ?
C8 C9 . 1.402(2) ?
C8 N1 . 1.4194(19) ?
C9 C10 . 1.380(2) ?
C9 C15 . 1.504(2) ?
C10 C11 . 1.374(2) ?
C10 H10 . 0.93 ?
C11 C12 . 1.373(2) ?
C11 H11 . 0.93 ?
C12 C13 . 1.376(2) ?
C12 H12 . 0.93 ?
C13 H13 . 0.93 ?
C14 H14A . 0.96 ?
C14 H14B . 0.96 ?
C14 H14C . 0.96 ?
C15 H15A . 0.96 ?
C15 H15B . 0.96 ?
C15 H15C . 0.96 ?
N1 H1N . 0.86 ?
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_545 0.86 2.13 2.9417(14) 157
C13 H13 O1 . 0.93 2.48 2.908(2) 108
C14 H14c Cg1 1_545 0.96 2.70 3.627(2) 161
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 . . . . 0.0(2) ?
C7 C1 C2 C3 . . . . -178.03(13) ?
C1 C2 C3 C4 . . . . -1.1(2) ?
C1 C2 C3 C14 . . . . 179.15(13) ?
C2 C3 C4 C5 . . . . 1.1(2) ?
C14 C3 C4 C5 . . . . -179.21(15) ?
C3 C4 C5 C6 . . . . 0.2(2) ?
C4 C5 C6 C1 . . . . -1.4(2) ?
C2 C1 C6 C5 . . . . 1.3(2) ?
C7 C1 C6 C5 . . . . 179.36(14) ?
C6 C1 C7 O1 . . . . -36.9(2) ?
C2 C1 C7 O1 . . . . 141.04(15) ?
C6 C1 C7 N1 . . . . 143.59(14) ?
C2 C1 C7 N1 . . . . -38.4(2) ?
C13 C8 C9 C10 . . . . 0.4(2) ?
N1 C8 C9 C10 . . . . -179.00(13) ?
C13 C8 C9 C15 . . . . -179.54(14) ?
N1 C8 C9 C15 . . . . 1.1(2) ?
C8 C9 C10 C11 . . . . -0.8(2) ?
C15 C9 C10 C11 . . . . 179.06(15) ?
C9 C10 C11 C12 . . . . 0.6(3) ?
C10 C11 C12 C13 . . . . 0.1(3) ?
C11 C12 C13 C8 . . . . -0.6(2) ?
C9 C8 C13 C12 . . . . 0.4(2) ?
N1 C8 C13 C12 . . . . 179.69(14) ?
O1 C7 N1 C8 . . . . -1.3(2) ?
C1 C7 N1 C8 . . . . 178.10(13) ?
C13 C8 N1 C7 . . . . 39.2(2) ?
C9 C8 N1 C7 . . . . -141.47(15) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 664014
