#------------------------------------------------------------------------------
#$Date: 2016-02-21 02:03:34 +0200 (Sun, 21 Feb 2016) $
#$Revision: 176798 $
#$URL: svn://www.crystallography.net/cod/cif/2/23/03/2230351.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_2230351
loop_
_publ_author_name
'Arslan, Hakan'
'Algul, Oztekin'
'Zirek, Selin'
'Tari, Ozden'
'Demircan, Aydın'
'Hardcastle, Kenneth I.'
_publ_section_title
;
 2-(4-Methoxy-2-methylanilino)-1,2-diphenylethanone
;
_journal_coeditor_code           HG5030
_journal_issue                   6
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1303
_journal_paper_doi               10.1107/S1600536811015960
_journal_volume                  67
_journal_year                    2011
_chemical_formula_iupac          'C22 H21 N O2'
_chemical_formula_moiety         'C22 H21 N O2'
_chemical_formula_sum            'C22 H21 N O2'
_chemical_formula_weight         331.40
_chemical_name_systematic
;
2-(4-Methoxy-2-methylanilino)-1,2-diphenylethanone
;
_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           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 100.544(15)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   12.570(12)
_cell_length_b                   8.009(8)
_cell_length_c                   18.091(17)
_cell_measurement_reflns_used    4852
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      24.50
_cell_measurement_theta_min      2.29
_cell_volume                     1791(3)
_computing_cell_refinement       'SAINT (Bruker, 2008)'
_computing_data_collection       'SMART (Bruker, 2008)'
_computing_data_reduction        'SAINT (Bruker, 2008)'
_computing_molecular_graphics    'OLEX2 (Dolomanov et al., 2009)'
_computing_publication_material
;
SHELXTL (Sheldrick, 2008), OLEX2 (Dolomanov et al.,
2009), publCIF
(Westrip, 2010) and Mercury (Macrae et al., 2006)
;
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker SMART CCD area-detector'
_diffrn_measurement_method       'φ and ω'
_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  0.0546
_diffrn_reflns_av_sigmaI/netI    0.0349
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            28799
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         27.50
_diffrn_reflns_theta_min         1.65
_exptl_absorpt_coefficient_mu    0.078
_exptl_absorpt_correction_T_max  0.9883
_exptl_absorpt_correction_T_min  0.9837
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2008)'
_exptl_crystal_colour            Yellow
_exptl_crystal_density_diffrn    1.229
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Block
_exptl_crystal_F_000             704
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.267
_refine_diff_density_min         -0.251
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     226
_refine_ls_number_reflns         4122
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.054
_refine_ls_R_factor_all          0.0660
_refine_ls_R_factor_gt           0.0420
_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0413P)²+0.4229P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0973
_refine_ls_wR_factor_ref         0.1115
_reflns_number_gt                2935
_reflns_number_total             4122
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            hg5030.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2230351
_cod_database_fobs_code          2230351
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_symmetry_multiplicity
_atom_site_disorder_assembly
_atom_site_disorder_group
C C1 0.70413(11) 0.71666(18) 0.13255(8) 0.0336(3) Uani d . 1 1 . .
C C2 0.65511(11) 0.79413(17) 0.05905(7) 0.0314(3) Uani d . 1 1 . .
C C3 0.70228(12) 0.92642(19) 0.02686(8) 0.0380(3) Uani d . 1 1 . .
H H3A 0.7667 0.9764 0.0533 0.046 Uiso calc R 1 1 . .
C C4 0.65510(14) 0.9856(2) -0.04399(8) 0.0453(4) Uani d . 1 1 . .
H H4A 0.6879 1.0748 -0.0662 0.054 Uiso calc R 1 1 . .
C C5 0.56034(14) 0.9144(2) -0.08206(8) 0.0436(4) Uani d . 1 1 . .
H H5A 0.5286 0.9546 -0.1305 0.052 Uiso calc R 1 1 . .
C C6 0.51179(13) 0.7853(2) -0.05009(8) 0.0420(4) Uani d . 1 1 . .
H H6A 0.4460 0.7385 -0.0761 0.050 Uiso calc R 1 1 . .
C C7 0.55897(12) 0.72392(18) 0.01989(8) 0.0361(3) Uani d . 1 1 . .
H H7A 0.5260 0.6339 0.0414 0.043 Uiso calc R 1 1 . .
C C8 0.78651(11) 0.81396(18) 0.19059(8) 0.0339(3) Uani d . 1 1 . .
H H8A 0.8385 0.8744 0.1644 0.041 Uiso calc R 1 1 . .
C C9 0.72052(11) 0.94044(17) 0.22728(7) 0.0297(3) Uani d . 1 1 . .
C C10 0.72302(12) 1.11045(18) 0.21167(8) 0.0370(3) Uani d . 1 1 . .
H H10A 0.7685 1.1508 0.1790 0.044 Uiso calc R 1 1 . .
C C11 0.65930(13) 1.22179(18) 0.24361(9) 0.0421(4) Uani d . 1 1 . .
H H11A 0.6615 1.3376 0.2327 0.051 Uiso calc R 1 1 . .
C C12 0.59250(12) 1.16418(19) 0.29135(8) 0.0396(4) Uani d . 1 1 . .
H H12A 0.5489 1.2403 0.3129 0.048 Uiso calc R 1 1 . .
C C13 0.58976(12) 0.99566(19) 0.30736(8) 0.0378(3) Uani d . 1 1 . .
H H13A 0.5441 0.9557 0.3399 0.045 Uiso calc R 1 1 . .
C C14 0.65372(11) 0.88458(18) 0.27584(8) 0.0334(3) Uani d . 1 1 . .
H H14A 0.6519 0.7691 0.2875 0.040 Uiso calc R 1 1 . .
C C15 0.91952(11) 0.72896(19) 0.30593(8) 0.0330(3) Uani d . 1 1 . .
C C16 0.95263(11) 0.59902(19) 0.35825(8) 0.0346(3) Uani d . 1 1 . .
C C17 1.02943(11) 0.6351(2) 0.42183(8) 0.0393(4) Uani d . 1 1 . .
H H17A 1.0524 0.5485 0.4570 0.047 Uiso calc R 1 1 . .
C C18 1.07393(12) 0.7936(2) 0.43580(8) 0.0412(4) Uani d . 1 1 . .
C C19 1.04216(12) 0.9204(2) 0.38448(8) 0.0409(4) Uani d . 1 1 . .
H H19A 1.0725 1.0289 0.3929 0.049 Uiso calc R 1 1 . .
C C20 0.96492(11) 0.88712(19) 0.32004(8) 0.0375(3) Uani d . 1 1 . .
H H20A 0.9429 0.9745 0.2851 0.045 Uiso calc R 1 1 . .
C C21 0.90500(13) 0.4262(2) 0.34587(9) 0.0442(4) Uani d . 1 1 . .
H H21A 0.9374 0.3535 0.3875 0.066 Uiso calc R 1 1 . .
H H21B 0.9201 0.3810 0.2985 0.066 Uiso calc R 1 1 . .
H H21C 0.8266 0.4318 0.3435 0.066 Uiso calc R 1 1 . .
C C22 1.19345(16) 0.9696(3) 0.52047(11) 0.0690(6) Uani d . 1 1 . .
H H22A 1.2440 0.9640 0.5686 0.103 Uiso calc R 1 1 . .
H H22B 1.1358 1.0496 0.5244 0.103 Uiso calc R 1 1 . .
H H22C 1.2322 1.0058 0.4810 0.103 Uiso calc R 1 1 . .
N N1 0.84386(10) 0.69119(16) 0.24129(7) 0.0412(3) Uani d . 1 1 . .
H H1A 0.8302 0.5852 0.2308 0.049 Uiso calc R 1 1 . .
O O1 0.67637(9) 0.57676(13) 0.14827(6) 0.0477(3) Uani d . 1 1 . .
O O2 1.14758(10) 0.80923(17) 0.50230(6) 0.0612(4) Uani d . 1 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
O1 C1 C2 . . 119.92(13) ?
O1 C1 C8 . . 119.27(13) ?
C2 C1 C8 . . 120.77(13) ?
C3 C2 C7 . . 119.18(14) ?
C3 C2 C1 . . 123.38(13) ?
C7 C2 C1 . . 117.39(13) ?
C2 C3 C4 . . 120.09(15) ?
C2 C3 H3A . . 120.0 ?
C4 C3 H3A . . 120.0 ?
C5 C4 C3 . . 119.99(16) ?
C5 C4 H4A . . 120.0 ?
C3 C4 H4A . . 120.0 ?
C6 C5 C4 . . 120.41(15) ?
C6 C5 H5A . . 119.8 ?
C4 C5 H5A . . 119.8 ?
C5 C6 C7 . . 120.02(15) ?
C5 C6 H6A . . 120.0 ?
C7 C6 H6A . . 120.0 ?
C6 C7 C2 . . 120.30(15) ?
C6 C7 H7A . . 119.9 ?
C2 C7 H7A . . 119.9 ?
N1 C8 C9 . . 114.91(13) ?
N1 C8 C1 . . 106.44(13) ?
C9 C8 C1 . . 106.20(12) ?
N1 C8 H8A . . 109.7 ?
C9 C8 H8A . . 109.7 ?
C1 C8 H8A . . 109.7 ?
C10 C9 C14 . . 118.68(13) ?
C10 C9 C8 . . 121.58(13) ?
C14 C9 C8 . . 119.71(13) ?
C9 C10 C11 . . 120.40(15) ?
C9 C10 H10A . . 119.8 ?
C11 C10 H10A . . 119.8 ?
C12 C11 C10 . . 120.28(15) ?
C12 C11 H11A . . 119.9 ?
C10 C11 H11A . . 119.9 ?
C13 C12 C11 . . 119.71(14) ?
C13 C12 H12A . . 120.1 ?
C11 C12 H12A . . 120.1 ?
C12 C13 C14 . . 120.05(15) ?
C12 C13 H13A . . 120.0 ?
C14 C13 H13A . . 120.0 ?
C13 C14 C9 . . 120.87(14) ?
C13 C14 H14A . . 119.6 ?
C9 C14 H14A . . 119.6 ?
C20 C15 N1 . . 122.87(13) ?
C20 C15 C16 . . 119.00(14) ?
N1 C15 C16 . . 118.12(14) ?
C17 C16 C15 . . 118.33(15) ?
C17 C16 C21 . . 120.70(13) ?
C15 C16 C21 . . 120.97(14) ?
C16 C17 C18 . . 122.38(14) ?
C16 C17 H17A . . 118.8 ?
C18 C17 H17A . . 118.8 ?
O2 C18 C19 . . 125.58(15) ?
O2 C18 C17 . . 115.06(13) ?
C19 C18 C17 . . 119.35(14) ?
C18 C19 C20 . . 119.34(15) ?
C18 C19 H19A . . 120.3 ?
C20 C19 H19A . . 120.3 ?
C15 C20 C19 . . 121.61(14) ?
C15 C20 H20A . . 119.2 ?
C19 C20 H20A . . 119.2 ?
C16 C21 H21A . . 109.5 ?
C16 C21 H21B . . 109.5 ?
H21A C21 H21B . . 109.5 ?
C16 C21 H21C . . 109.5 ?
H21A C21 H21C . . 109.5 ?
H21B C21 H21C . . 109.5 ?
O2 C22 H22A . . 109.5 ?
O2 C22 H22B . . 109.5 ?
H22A C22 H22B . . 109.5 ?
O2 C22 H22C . . 109.5 ?
H22A C22 H22C . . 109.5 ?
H22B C22 H22C . . 109.5 ?
C15 N1 C8 . . 124.59(13) ?
C15 N1 H1A . . 117.7 ?
C8 N1 H1A . . 117.7 ?
C18 O2 C22 . . 117.49(13) ?
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 O1 . 1.2226(19) ?
C1 C2 . 1.494(2) ?
C1 C8 . 1.544(2) ?
C2 C3 . 1.393(2) ?
C2 C7 . 1.402(2) ?
C3 C4 . 1.393(2) ?
C3 H3A . 0.9500 ?
C4 C5 . 1.385(2) ?
C4 H4A . 0.9500 ?
C5 C6 . 1.380(2) ?
C5 H5A . 0.9500 ?
C6 C7 . 1.386(2) ?
C6 H6A . 0.9500 ?
C7 H7A . 0.9500 ?
C8 N1 . 1.4443(19) ?
C8 C9 . 1.535(2) ?
C8 H8A . 1.0000 ?
C9 C10 . 1.392(2) ?
C9 C14 . 1.395(2) ?
C10 C11 . 1.393(2) ?
C10 H10A . 0.9500 ?
C11 C12 . 1.389(2) ?
C11 H11A . 0.9500 ?
C12 C13 . 1.382(2) ?
C12 H12A . 0.9500 ?
C13 C14 . 1.390(2) ?
C13 H13A . 0.9500 ?
C14 H14A . 0.9500 ?
C15 C20 . 1.394(2) ?
C15 N1 . 1.399(2) ?
C15 C16 . 1.417(2) ?
C16 C17 . 1.390(2) ?
C16 C21 . 1.509(2) ?
C17 C18 . 1.391(2) ?
C17 H17A . 0.9500 ?
C18 O2 . 1.383(2) ?
C18 C19 . 1.385(2) ?
C19 C20 . 1.399(2) ?
C19 H19A . 0.9500 ?
C20 H20A . 0.9500 ?
C21 H21A . 0.9800 ?
C21 H21B . 0.9800 ?
C21 H21C . 0.9800 ?
C22 O2 . 1.422(2) ?
C22 H22A . 0.9800 ?
C22 H22B . 0.9800 ?
C22 H22C . 0.9800 ?
N1 H1A . 0.8800 ?
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 H1A O1 . 0.88 2.22 2.609(3) 107
C11 H11A O1 1_565 0.95 2.48 3.352(4) 153
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
O1 C1 C2 C3 . . . . -160.36(14) ?
C8 C1 C2 C3 . . . . 22.1(2) ?
O1 C1 C2 C7 . . . . 17.0(2) ?
C8 C1 C2 C7 . . . . -160.60(12) ?
C7 C2 C3 C4 . . . . -1.2(2) ?
C1 C2 C3 C4 . . . . 176.15(14) ?
C2 C3 C4 C5 . . . . 0.9(2) ?
C3 C4 C5 C6 . . . . 0.3(2) ?
C4 C5 C6 C7 . . . . -1.3(2) ?
C5 C6 C7 C2 . . . . 1.0(2) ?
C3 C2 C7 C6 . . . . 0.2(2) ?
C1 C2 C7 C6 . . . . -177.25(13) ?
O1 C1 C8 N1 . . . . 21.30(18) ?
C2 C1 C8 N1 . . . . -161.10(12) ?
O1 C1 C8 C9 . . . . -101.58(16) ?
C2 C1 C8 C9 . . . . 76.02(16) ?
N1 C8 C9 C10 . . . . 135.07(14) ?
C1 C8 C9 C10 . . . . -107.56(15) ?
N1 C8 C9 C14 . . . . -46.83(17) ?
C1 C8 C9 C14 . . . . 70.54(15) ?
C14 C9 C10 C11 . . . . -0.5(2) ?
C8 C9 C10 C11 . . . . 177.64(12) ?
C9 C10 C11 C12 . . . . -0.1(2) ?
C10 C11 C12 C13 . . . . 0.3(2) ?
C11 C12 C13 C14 . . . . 0.1(2) ?
C12 C13 C14 C9 . . . . -0.6(2) ?
C10 C9 C14 C13 . . . . 0.8(2) ?
C8 C9 C14 C13 . . . . -177.33(12) ?
C20 C15 C16 C17 . . . . 0.0(2) ?
N1 C15 C16 C17 . . . . 178.73(13) ?
C20 C15 C16 C21 . . . . 179.37(13) ?
N1 C15 C16 C21 . . . . -1.9(2) ?
C15 C16 C17 C18 . . . . 0.4(2) ?
C21 C16 C17 C18 . . . . -178.96(14) ?
C16 C17 C18 O2 . . . . 178.75(13) ?
C16 C17 C18 C19 . . . . -0.8(2) ?
O2 C18 C19 C20 . . . . -178.70(14) ?
C17 C18 C19 C20 . . . . 0.8(2) ?
N1 C15 C20 C19 . . . . -178.65(14) ?
C16 C15 C20 C19 . . . . 0.0(2) ?
C18 C19 C20 C15 . . . . -0.4(2) ?
C20 C15 N1 C8 . . . . -14.1(2) ?
C16 C15 N1 C8 . . . . 167.24(13) ?
C9 C8 N1 C15 . . . . -57.18(19) ?
C1 C8 N1 C15 . . . . -174.41(13) ?
C19 C18 O2 C22 . . . . 1.2(2) ?
C17 C18 O2 C22 . . . . -178.33(16) ?
