#------------------------------------------------------------------------------
#$Date: 2016-02-20 22:30:07 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176789 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/55/2225510.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_2225510
loop_
_publ_author_name
'Gowda, B. Thimme'
'Tokarčík, Miroslav'
'Kožíšek, Jozef'
'Rodrigues, Vinola Zeena'
'Fuess, Hartmut'
_publ_section_title
;
 N-(2,5-Dimethylphenyl)-2-methylbenzamide
;
_journal_coeditor_code           DN2545
_journal_issue                   4
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o815
_journal_paper_doi               10.1107/S160053681000886X
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C16 H17 N O'
_chemical_formula_moiety         'C16 H17 N O'
_chemical_formula_sum            'C16 H17 N O'
_chemical_formula_weight         239.31
_chemical_name_systematic
;
N-(2,5-Dimethylphenyl)-2-methylbenzamide
;
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_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                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   4.90104(10)
_cell_length_b                   5.85657(16)
_cell_length_c                   45.8291(12)
_cell_measurement_reflns_used    11414
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      29.4578
_cell_measurement_theta_min      1.7726
_cell_volume                     1315.45(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 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device       '4-circle kappa geometry goniometer'
_diffrn_measurement_device_type  'Oxford Diffraction Xcalibur Ruby Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0369
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       54
_diffrn_reflns_limit_l_min       -54
_diffrn_reflns_number            22131
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25
_diffrn_reflns_theta_min         1.78
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.075
_exptl_absorpt_correction_T_max  0.990
_exptl_absorpt_correction_T_min  0.957
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(CrysAlis Pro; Oxford Diffraction, 2009)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.208
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             512
_exptl_crystal_size_max          0.54
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.09
_refine_diff_density_max         0.122
_refine_diff_density_min         -0.127
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.199
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     165
_refine_ls_number_reflns         1414
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.199
_refine_ls_R_factor_all          0.0471
_refine_ls_R_factor_gt           0.0435
_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)+(0.0248P)²+0.5849P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0954
_refine_ls_wR_factor_ref         0.0968
_reflns_number_gt                1338
_reflns_number_total             1414
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            dn2545.cif
_cod_data_source_block           I
_cod_database_code               2225510
_cod_database_fobs_code          2225510
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -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
O O1 0.1938(4) 0.2752(5) 0.11488(4) 0.0571(7) Uani d . 1 . .
N N1 0.6250(4) 0.2075(4) 0.12991(4) 0.0354(5) Uani d . 1 . .
H H1N 0.7945 0.2132 0.1251 0.043 Uiso d R 1 . .
C C1 0.4388(5) 0.2701(5) 0.10975(5) 0.0345(6) Uani d . 1 . .
C C2 0.5509(5) 0.3297(5) 0.08026(5) 0.0340(6) Uani d . 1 . .
C C3 0.4651(6) 0.5263(5) 0.06577(6) 0.0436(7) Uani d . 1 . .
C C4 0.5758(7) 0.5680(6) 0.03829(6) 0.0580(9) Uani d . 1 . .
H H4 0.5241 0.6989 0.0282 0.070 Uiso calc R 1 . .
C C5 0.7593(7) 0.4208(7) 0.02570(6) 0.0644(10) Uani d . 1 . .
H H5 0.8294 0.4532 0.0073 0.077 Uiso calc R 1 . .
C C6 0.8400(7) 0.2271(7) 0.03994(6) 0.0600(9) Uani d . 1 . .
H H6 0.9627 0.1267 0.0313 0.072 Uiso calc R 1 . .
C C7 0.7366(6) 0.1831(5) 0.06728(6) 0.0446(7) Uani d . 1 . .
H H7 0.7924 0.0528 0.0772 0.054 Uiso calc R 1 . .
C C8 0.5574(5) 0.1322(4) 0.15873(5) 0.0323(6) Uani d . 1 . .
C C9 0.6678(6) -0.0703(5) 0.16930(6) 0.0382(6) Uani d . 1 . .
C C10 0.5923(6) -0.1364(5) 0.19709(6) 0.0484(8) Uani d . 1 . .
H H10 0.6660 -0.2696 0.2048 0.058 Uiso calc R 1 . .
C C11 0.4121(6) -0.0122(5) 0.21371(6) 0.0488(8) Uani d . 1 . .
H H11 0.3631 -0.0644 0.2321 0.059 Uiso calc R 1 . .
C C12 0.3027(6) 0.1906(5) 0.20322(5) 0.0399(7) Uani d . 1 . .
C C13 0.3794(5) 0.2610(5) 0.17554(5) 0.0365(6) Uani d . 1 . .
H H13 0.3103 0.3969 0.1681 0.044 Uiso calc R 1 . .
C C14 0.2646(7) 0.6906(6) 0.07875(8) 0.0633(9) Uani d . 1 . .
H H14A 0.2576 0.8264 0.0670 0.095 Uiso calc R 1 . .
H H14B 0.3206 0.7294 0.0982 0.095 Uiso calc R 1 . .
H H14C 0.0872 0.6213 0.0793 0.095 Uiso calc R 1 . .
C C15 0.8619(6) -0.2117(5) 0.15136(6) 0.0527(8) Uani d . 1 . .
H H15A 1.0349 -0.1354 0.1502 0.079 Uiso calc R 1 . .
H H15B 0.7888 -0.2316 0.1321 0.079 Uiso calc R 1 . .
H H15C 0.8857 -0.3583 0.1604 0.079 Uiso calc R 1 . .
C C16 0.1035(7) 0.3287(6) 0.22091(6) 0.0566(9) Uani d . 1 . .
H H16A 0.1199 0.2888 0.2412 0.068 Uiso d PR 0.74 . .
H H16B -0.0786 0.2971 0.2144 0.068 Uiso d PR 0.74 . .
H H16C 0.1420 0.4883 0.2185 0.068 Uiso d PR 0.74 . .
H H16D 0.0025 0.4276 0.2082 0.068 Uiso d PR 0.26 . .
H H16E 0.2007 0.4188 0.2350 0.068 Uiso d PR 0.26 . .
H H16F -0.0201 0.2279 0.2309 0.068 Uiso d PR 0.26 . .
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 '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 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0 '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
C1 N1 C8 . . 124.0(2) ?
C1 N1 H1N . . 117.9 ?
C8 N1 H1N . . 118.1 ?
O1 C1 N1 . . 122.6(2) ?
O1 C1 C2 . . 121.8(2) ?
N1 C1 C2 . . 115.6(2) ?
C7 C2 C3 . . 120.4(3) ?
C7 C2 C1 . . 118.9(2) ?
C3 C2 C1 . . 120.7(2) ?
C4 C3 C2 . . 117.3(3) ?
C4 C3 C14 . . 120.1(3) ?
C2 C3 C14 . . 122.6(3) ?
C5 C4 C3 . . 121.7(3) ?
C5 C4 H4 . . 119.2 ?
C3 C4 H4 . . 119.2 ?
C6 C5 C4 . . 120.7(3) ?
C6 C5 H5 . . 119.7 ?
C4 C5 H5 . . 119.7 ?
C5 C6 C7 . . 118.9(3) ?
C5 C6 H6 . . 120.5 ?
C7 C6 H6 . . 120.5 ?
C6 C7 C2 . . 121.1(3) ?
C6 C7 H7 . . 119.4 ?
C2 C7 H7 . . 119.4 ?
C13 C8 C9 . . 121.0(2) ?
C13 C8 N1 . . 119.4(2) ?
C9 C8 N1 . . 119.6(2) ?
C10 C9 C8 . . 117.1(3) ?
C10 C9 C15 . . 121.2(3) ?
C8 C9 C15 . . 121.6(2) ?
C11 C10 C9 . . 122.3(3) ?
C11 C10 H10 . . 118.8 ?
C9 C10 H10 . . 118.8 ?
C10 C11 C12 . . 120.6(3) ?
C10 C11 H11 . . 119.7 ?
C12 C11 H11 . . 119.7 ?
C13 C12 C11 . . 117.8(3) ?
C13 C12 C16 . . 120.6(3) ?
C11 C12 C16 . . 121.6(3) ?
C12 C13 C8 . . 121.2(3) ?
C12 C13 H13 . . 119.4 ?
C8 C13 H13 . . 119.4 ?
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 ?
C12 C16 H16A . . 109.6 ?
C12 C16 H16B . . 109.3 ?
H16A C16 H16B . . 109.5 ?
C12 C16 H16C . . 109.4 ?
H16A C16 H16C . . 109.5 ?
H16B C16 H16C . . 109.5 ?
C12 C16 H16D . . 109.3 ?
H16A C16 H16D . . 141.1 ?
H16B C16 H16D . . 56.4 ?
H16C C16 H16D . . 56.1 ?
C12 C16 H16E . . 109.6 ?
H16A C16 H16E . . 56.2 ?
H16B C16 H16E . . 141.1 ?
H16C C16 H16E . . 56.3 ?
H16D C16 H16E . . 109.4 ?
C12 C16 H16F . . 109.5 ?
H16A C16 H16F . . 56.3 ?
H16B C16 H16F . . 56.2 ?
H16C C16 H16F . . 141.1 ?
H16D C16 H16F . . 109.5 ?
H16E C16 H16F . . 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 C1 . 1.224(3) ?
N1 C1 . 1.349(3) ?
N1 C8 . 1.431(3) ?
N1 H1N . 0.8598 ?
C1 C2 . 1.500(3) ?
C2 C7 . 1.386(4) ?
C2 C3 . 1.394(4) ?
C3 C4 . 1.393(4) ?
C3 C14 . 1.499(4) ?
C4 C5 . 1.373(5) ?
C4 H4 . 0.9300 ?
C5 C6 . 1.367(5) ?
C5 H5 . 0.9300 ?
C6 C7 . 1.376(4) ?
C6 H6 . 0.9300 ?
C7 H7 . 0.9300 ?
C8 C13 . 1.387(3) ?
C8 C9 . 1.391(4) ?
C9 C10 . 1.381(4) ?
C9 C15 . 1.505(4) ?
C10 C11 . 1.375(4) ?
C10 H10 . 0.9300 ?
C11 C12 . 1.389(4) ?
C11 H11 . 0.9300 ?
C12 C13 . 1.386(3) ?
C12 C16 . 1.505(4) ?
C13 H13 . 0.9300 ?
C14 H14A . 0.9600 ?
C14 H14B . 0.9600 ?
C14 H14C . 0.9600 ?
C15 H15A . 0.9600 ?
C15 H15B . 0.9600 ?
C15 H15C . 0.9600 ?
C16 H16A . 0.9599 ?
C16 H16B . 0.9598 ?
C16 H16C . 0.9602 ?
C16 H16D . 0.9605 ?
C16 H16E . 0.9588 ?
C16 H16F . 0.9607 ?
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_655 0.86 2.05 2.899(3) 171.9
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
C8 N1 C1 O1 . . . . 2.7(5) ?
C8 N1 C1 C2 . . . . -176.3(2) ?
O1 C1 C2 C7 . . . . -130.9(3) ?
N1 C1 C2 C7 . . . . 48.1(3) ?
O1 C1 C2 C3 . . . . 47.5(4) ?
N1 C1 C2 C3 . . . . -133.5(3) ?
C7 C2 C3 C4 . . . . -0.7(4) ?
C1 C2 C3 C4 . . . . -179.1(3) ?
C7 C2 C3 C14 . . . . 180.0(3) ?
C1 C2 C3 C14 . . . . 1.5(4) ?
C2 C3 C4 C5 . . . . 0.8(4) ?
C14 C3 C4 C5 . . . . -179.8(3) ?
C3 C4 C5 C6 . . . . -0.1(5) ?
C4 C5 C6 C7 . . . . -0.7(5) ?
C5 C6 C7 C2 . . . . 0.9(5) ?
C3 C2 C7 C6 . . . . -0.2(4) ?
C1 C2 C7 C6 . . . . 178.3(3) ?
C1 N1 C8 C13 . . . . -49.7(4) ?
C1 N1 C8 C9 . . . . 129.3(3) ?
C13 C8 C9 C10 . . . . 0.0(4) ?
N1 C8 C9 C10 . . . . -179.1(3) ?
C13 C8 C9 C15 . . . . -179.8(3) ?
N1 C8 C9 C15 . . . . 1.1(4) ?
C8 C9 C10 C11 . . . . 1.3(4) ?
C15 C9 C10 C11 . . . . -178.9(3) ?
C9 C10 C11 C12 . . . . -1.6(5) ?
C10 C11 C12 C13 . . . . 0.6(4) ?
C10 C11 C12 C16 . . . . 179.5(3) ?
C11 C12 C13 C8 . . . . 0.6(4) ?
C16 C12 C13 C8 . . . . -178.3(2) ?
C9 C8 C13 C12 . . . . -0.9(4) ?
N1 C8 C13 C12 . . . . 178.1(2) ?
