#------------------------------------------------------------------------------
#$Date: 2017-10-13 03:48:21 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201957 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/01/52/2015292.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_2015292
loop_
_publ_author_name
'Batsanov, Andrei S.'
'Goeta, Andrés E.'
'Howard, Judith A. K.'
'Soto, Bernardino'
'Au-Alvarez, Oscar'
_publ_section_title
;
 2-(4-Chloroanilino)- and 2-(4-methoxyanilino)-1,2-diphenylethanone
;
_journal_coeditor_code           DN3012
_journal_issue                   5
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              o304
_journal_page_last               o306
_journal_paper_doi               10.1107/S0108270106012881
_journal_volume                  62
_journal_year                    2006
_chemical_formula_iupac          'C21 H19 N O2'
_chemical_formula_moiety         'C21 H19 N O2'
_chemical_formula_sum            'C21 H19 N O2'
_chemical_formula_weight         317.37
_chemical_melting_point          374(1)
_chemical_name_systematic
;
2-(4-methoxyanilino)-1,2-diphenylethanone
;
_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                90.00
_cell_angle_beta                 91.750(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   5.8230(8)
_cell_length_b                   10.0690(10)
_cell_length_c                   27.316(3)
_cell_measurement_reflns_used    6872
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      29.99
_cell_measurement_theta_min      2.51
_cell_volume                     1600.8(3)
_computing_cell_refinement       'SAINT (Version 6.02A; Bruker, 2001)'
_computing_data_collection       'SMART (Bruker, 2001)'
_computing_data_reduction        'SAINT (Version 6.02A)'
_computing_molecular_graphics    SHELXTL
_computing_publication_material  SHELXTL
_computing_structure_refinement  SHELXTL
_computing_structure_solution    'SHELXTL (Bruker, 2003)'
_diffrn_ambient_temperature      120(2)
_diffrn_detector_area_resol_mean 5.6
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker SMART CCD 6K area-detector'
_diffrn_measurement_method       'ω scans'
_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  0.0358
_diffrn_reflns_av_sigmaI/netI    0.0325
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       38
_diffrn_reflns_limit_l_min       -38
_diffrn_reflns_number            21531
_diffrn_reflns_theta_full        30.00
_diffrn_reflns_theta_max         30.00
_diffrn_reflns_theta_min         2.51
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.084
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            'light yellow'
_exptl_crystal_density_diffrn    1.317
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             672
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.398
_refine_diff_density_min         -0.213
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     223
_refine_ls_number_reflns         4666
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.024
_refine_ls_R_factor_all          0.0544
_refine_ls_R_factor_gt           0.0430
_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)+(0.0577P)²+0.5575P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1100
_refine_ls_wR_factor_ref         0.1194
_reflns_number_gt                3800
_reflns_number_total             4666
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            dn3012.cif
_cod_data_source_block           II
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               2015292
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
N N 0.19628(17) 0.28342(9) 0.11117(4) 0.0222(2) Uani d . 1
H H1 0.067(3) 0.2666(15) 0.0950(6) 0.026(4) Uiso d . 1
O O1 -0.11470(13) 0.46729(8) 0.08278(3) 0.02488(18) Uani d . 1
O O2 0.77405(15) -0.15195(8) 0.14065(3) 0.0287(2) Uani d . 1
C C1 0.08626(18) 0.49977(10) 0.08100(4) 0.0181(2) Uani d . 1
C C2 0.26892(18) 0.42084(10) 0.11040(4) 0.0181(2) Uani d . 1
H H2 0.4204 0.4282 0.0943 0.022 Uiso d R 1
C C3 0.15455(18) 0.61727(10) 0.05166(4) 0.0178(2) Uani d . 1
C C4 0.37032(18) 0.62806(10) 0.03097(4) 0.0194(2) Uani d . 1
H H4 0.4870 0.5650 0.0390 0.023 Uiso d R 1
C C5 0.41413(19) 0.73133(11) -0.00134(4) 0.0218(2) Uani d . 1
H H5 0.5590 0.7367 -0.0163 0.026 Uiso d R 1
C C6 0.2471(2) 0.82639(11) -0.01184(4) 0.0231(2) Uani d . 1
H H6 0.2771 0.8963 -0.0341 0.028 Uiso d R 1
C C7 0.0354(2) 0.81881(11) 0.01035(4) 0.0230(2) Uani d . 1
H H7 -0.0771 0.8855 0.0041 0.028 Uiso d R 1
C C8 -0.01151(18) 0.71431(11) 0.04151(4) 0.0204(2) Uani d . 1
H H8 -0.1574 0.7086 0.0560 0.024 Uiso d R 1
C C9 0.28350(18) 0.48648(10) 0.16094(4) 0.0183(2) Uani d . 1
C C10 0.1163(2) 0.46034(11) 0.19502(4) 0.0245(2) Uani d . 1
H H10 -0.0016 0.3977 0.1875 0.029 Uiso d R 1
C C11 0.1208(2) 0.52515(13) 0.23988(4) 0.0283(2) Uani d . 1
H H11 0.0070 0.5062 0.2631 0.034 Uiso d R 1
C C12 0.2914(2) 0.61755(13) 0.25093(4) 0.0284(3) Uani d . 1
H H12 0.2934 0.6628 0.2815 0.034 Uiso d R 1
C C13 0.4585(2) 0.64357(13) 0.21727(5) 0.0300(3) Uani d . 1
H H13 0.5762 0.7062 0.2249 0.036 Uiso d R 1
C C14 0.4554(2) 0.57833(12) 0.17219(4) 0.0239(2) Uani d . 1
H H14 0.5705 0.5967 0.1492 0.029 Uiso d R 1
C C15 0.35234(18) 0.17987(10) 0.11737(4) 0.0183(2) Uani d . 1
C C16 0.29076(19) 0.05237(10) 0.10095(4) 0.0204(2) Uani d . 1
H H16 0.1474 0.0395 0.0841 0.024 Uiso d R 1
C C17 0.4356(2) -0.05490(11) 0.10894(4) 0.0223(2) Uani d . 1
H H17 0.3910 -0.1404 0.0974 0.027 Uiso d R 1
C C18 0.64624(19) -0.03843(11) 0.13369(4) 0.0207(2) Uani d . 1
C C19 0.71295(19) 0.08765(11) 0.14904(4) 0.0213(2) Uani d . 1
H H19 0.8582 0.1003 0.1652 0.026 Uiso d R 1
C C20 0.56666(18) 0.19610(10) 0.14085(4) 0.0203(2) Uani d . 1
H H20 0.6140 0.2820 0.1514 0.024 Uiso d R 1
C C21 0.9481(2) -0.14996(13) 0.17847(5) 0.0296(3) Uani d . 1
H H21A 1.0710 -0.0891 0.1694 0.039(3) Uiso d R 1
H H21B 1.0111 -0.2395 0.1830 0.039(3) Uiso d R 1
H H21C 0.8817 -0.1198 0.2091 0.039(3) Uiso d R 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
_geom_angle_publ_flag
C15 N C2 121.91(9) yes
C15 N H1 117.7(10) yes
C2 N H1 115.0(10) yes
C18 O2 C21 117.31(9) ?
O1 C1 C3 120.49(9) ?
O1 C1 C2 119.45(9) ?
C3 C1 C2 120.04(9) ?
N C2 C9 114.07(9) ?
N C2 C1 107.73(8) ?
C9 C2 C1 105.47(8) ?
N C2 H2 109.9 ?
C9 C2 H2 109.8 ?
C1 C2 H2 109.8 ?
C8 C3 C4 119.40(10) ?
C8 C3 C1 117.90(9) ?
C4 C3 C1 122.49(9) ?
C5 C4 C3 119.92(10) ?
C5 C4 H4 120.0 ?
C3 C4 H4 120.0 ?
C6 C5 C4 120.32(10) ?
C6 C5 H5 119.8 ?
C4 C5 H5 119.8 ?
C5 C6 C7 119.76(10) ?
C5 C6 H6 120.1 ?
C7 C6 H6 120.1 ?
C8 C7 C6 120.19(10) ?
C8 C7 H7 119.9 ?
C6 C7 H7 119.9 ?
C7 C8 C3 120.32(10) ?
C7 C8 H8 119.8 ?
C3 C8 H8 119.8 ?
C14 C9 C10 119.42(10) ?
C14 C9 C2 120.42(10) ?
C10 C9 C2 120.05(10) ?
C11 C10 C9 120.44(11) ?
C11 C10 H10 119.8 ?
C9 C10 H10 119.8 ?
C12 C11 C10 120.11(11) ?
C12 C11 H11 119.9 ?
C10 C11 H11 119.9 ?
C13 C12 C11 119.70(11) ?
C13 C12 H12 120.2 ?
C11 C12 H12 120.1 ?
C12 C13 C14 120.46(11) ?
C12 C13 H13 119.8 ?
C14 C13 H13 119.8 ?
C9 C14 C13 119.87(11) ?
C9 C14 H14 120.1 ?
C13 C14 H14 120.1 ?
N C15 C20 122.71(10) ?
N C15 C16 119.19(10) ?
C20 C15 C16 118.07(10) ?
C17 C16 C15 121.01(10) ?
C17 C16 H16 119.5 ?
C15 C16 H16 119.5 ?
C16 C17 C18 120.49(10) ?
C16 C17 H17 119.8 ?
C18 C17 H17 119.8 ?
O2 C18 C19 124.98(10) ?
O2 C18 C17 115.70(10) ?
C19 C18 C17 119.32(10) ?
C18 C19 C20 120.13(10) ?
C18 C19 H19 119.9 ?
C20 C19 H19 119.9 ?
C15 C20 C19 120.93(10) ?
C15 C20 H20 119.5 ?
C19 C20 H20 119.5 ?
O2 C21 H21A 109.5 ?
O2 C21 H21B 109.5 ?
H21A C21 H21B 109.5 ?
O2 C21 H21C 109.4 ?
H21A C21 H21C 109.5 ?
H21B C21 H21C 109.5 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
N C15 1.3900(13) yes
N C2 1.4472(13) yes
N H1 0.878(15) ?
O1 C1 1.2174(13) yes
O2 C18 1.3741(13) ?
O2 C21 1.4250(15) ?
C1 C3 1.4898(14) yes
C1 C2 1.5348(14) yes
C2 C9 1.5306(15) ?
C2 H2 1.0000 ?
C3 C8 1.3965(14) ?
C3 C4 1.3976(15) ?
C4 C5 1.3926(15) ?
C4 H4 0.9500 ?
C5 C6 1.3885(16) ?
C5 H5 0.9500 ?
C6 C7 1.3919(17) ?
C6 H6 0.9500 ?
C7 C8 1.3859(15) ?
C7 H7 0.9500 ?
C8 H8 0.9500 ?
C9 C14 1.3902(15) ?
C9 C10 1.3926(15) ?
C10 C11 1.3877(17) ?
C10 H10 0.9500 ?
C11 C12 1.3875(18) ?
C11 H11 0.9500 ?
C12 C13 1.3838(18) ?
C12 H12 0.9500 ?
C13 C14 1.3954(17) ?
C13 H13 0.9500 ?
C14 H14 0.9500 ?
C15 C20 1.3951(15) ?
C15 C16 1.4030(14) ?
C16 C17 1.3835(15) ?
C16 H16 0.9500 ?
C17 C18 1.3923(16) ?
C17 H17 0.9500 ?
C18 C19 1.3887(15) ?
C19 C20 1.3988(15) ?
C19 H19 0.9500 ?
C20 H20 0.9500 ?
C21 H21A 0.9800 ?
C21 H21B 0.9800 ?
C21 H21C 0.9800 ?
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 H1 O1 . 0.878(15) 2.300(15) 2.6875(12) 106.7(12) yes
N H1 C6 3_565 0.878(15) 3.021(16) 3.8499(16) 158.1(13) 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
_geom_torsion_publ_flag
C8 C3 C1 O1 22.78(15) ?
C8 C3 C1 C2 -155.56(10) ?
C3 C1 C2 N -147.78(9) yes
C1 C2 N C15 154.74(10) yes
C2 N C15 C16 -157.45(10) ?
O1 C1 C2 N 33.86(13) yes
C1 C2 C9 C10 78.01(12) ?
N C2 C9 C10 -40.01(14) ?
C19 C18 O2 C21 20.68(16) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 222285
