#------------------------------------------------------------------------------
#$Date: 2017-10-13 03:48:21 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201957 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/01/52/2015291.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_2015291
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          'C20 H16 Cl N O'
_chemical_formula_moiety         'C20 H16 Cl N O'
_chemical_formula_sum            'C20 H16 Cl N O'
_chemical_formula_weight         321.79
_chemical_melting_point          436.0(10)
_chemical_name_systematic
;
2-(4-chloroaniline)-1,2-diphenylethanone
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                113.470(10)
_cell_angle_beta                 100.390(10)
_cell_angle_gamma                97.290(10)
_cell_formula_units_Z            2
_cell_length_a                   5.7748(8)
_cell_length_b                   11.485(2)
_cell_length_c                   13.086(2)
_cell_measurement_reflns_used    4129
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      29.30
_cell_measurement_theta_min      3.16
_cell_volume                     763.8(2)
_computing_cell_refinement       'SAINT (Version 6.45A; Bruker, 2003)'
_computing_data_collection       'SMART (Bruker, 2001)'
_computing_data_reduction        'SAINT (Version 6.45A)'
_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 8
_diffrn_measured_fraction_theta_full 0.982
_diffrn_measured_fraction_theta_max 0.982
_diffrn_measurement_device_type  'ProteumM APEX CCD area-detector'
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source
'60W microfocus Bede Microsource with glass polycapillary optics'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0986
_diffrn_reflns_av_sigmaI/netI    0.0791
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            8385
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         27.50
_diffrn_reflns_theta_min         3.16
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.254
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.399
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       'thin plate'
_exptl_crystal_F_000             336
_exptl_crystal_size_max          0.52
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.379
_refine_diff_density_min         -0.203
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     212
_refine_ls_number_reflns         3452
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.059
_refine_ls_R_factor_all          0.0446
_refine_ls_R_factor_gt           0.0372
_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)+(0.0218P)²+0.0976P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0977
_refine_ls_wR_factor_ref         0.1007
_reflns_number_gt                2860
_reflns_number_total             3452
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            dn3012.cif
_cod_data_source_block           I
_cod_database_code               2015291
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -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
Cl Cl 1.71577(6) 0.46113(4) 0.88681(3) 0.02593(12) Uani d . 1
O O1 0.45508(17) -0.00405(10) 0.35124(10) 0.0240(2) Uani d . 1
N N 0.8733(2) 0.12372(12) 0.49961(11) 0.0182(3) Uani d . 1
H H1 0.751(3) 0.0962(17) 0.5136(16) 0.029(5) Uiso d . 1
C C1 0.6187(2) 0.00749(13) 0.30583(13) 0.0171(3) Uani d . 1
C C2 0.8650(2) 0.09654(13) 0.38132(12) 0.0160(3) Uani d . 1
H H2 0.9965 0.0511 0.3579 0.019 Uiso d R 1
C C3 0.5800(2) -0.06112(13) 0.17882(13) 0.0179(3) Uani d . 1
C C4 0.7621(3) -0.05376(14) 0.12232(14) 0.0237(3) Uani d . 1
H H4 0.9184 -0.0015 0.1656 0.028 Uiso d R 1
C C5 0.7152(3) -0.12205(15) 0.00382(15) 0.0279(4) Uani d . 1
H H5 0.8386 -0.1149 -0.0338 0.034 Uiso d R 1
C C6 0.4906(3) -0.20073(16) -0.05995(15) 0.0298(4) Uani d . 1
H H6 0.4595 -0.2475 -0.1412 0.036 Uiso d R 1
C C7 0.3104(3) -0.21092(16) -0.00462(14) 0.0295(4) Uani d . 1
H H7 0.1567 -0.2664 -0.0479 0.035 Uiso d R 1
C C8 0.3538(3) -0.14060(15) 0.11298(14) 0.0233(3) Uani d . 1
H H8 0.2280 -0.1465 0.1497 0.028 Uiso d R 1
C C9 0.8911(2) 0.22060(13) 0.36177(12) 0.0160(3) Uani d . 1
C C10 0.7374(2) 0.30467(13) 0.39645(13) 0.0184(3) Uani d . 1
H H10 0.6192 0.2852 0.4327 0.022 Uiso d R 1
C C11 0.7549(3) 0.41642(14) 0.37888(14) 0.0218(3) Uani d . 1
H H11 0.6493 0.4731 0.4032 0.026 Uiso d R 1
C C12 0.9266(3) 0.44563(14) 0.32580(14) 0.0232(3) Uani d . 1
H H12 0.9365 0.5213 0.3123 0.028 Uiso d R 1
C C13 1.0831(2) 0.36414(15) 0.29262(14) 0.0226(3) Uani d . 1
H H13 1.2026 0.3846 0.2575 0.027 Uiso d R 1
C C14 1.0659(2) 0.25224(14) 0.31067(13) 0.0188(3) Uani d . 1
H H14 1.1743 0.1968 0.2879 0.023 Uiso d R 1
C C15 1.0720(2) 0.19796(13) 0.58880(12) 0.0152(3) Uani d . 1
C C16 1.0584(2) 0.23800(13) 0.70349(13) 0.0176(3) Uani d . 1
H H16 0.9117 0.2100 0.7187 0.021 Uiso d R 1
C C17 1.2533(2) 0.31719(14) 0.79477(13) 0.0195(3) Uani d . 1
H H17 1.2404 0.3432 0.8717 0.023 Uiso d R 1
C C18 1.4688(2) 0.35861(14) 0.77318(13) 0.0184(3) Uani d . 1
C C19 1.4890(2) 0.31783(13) 0.66101(13) 0.0179(3) Uani d . 1
H H19 1.6373 0.3448 0.6466 0.021 Uiso d R 1
C C20 1.2943(2) 0.23808(13) 0.56997(13) 0.0173(3) Uani d . 1
H H20 1.3109 0.2099 0.4934 0.021 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'
Cl Cl 0.1484 0.1585 '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 122.94(11) yes
C15 N H1 119.2(14) yes
C2 N H1 117.8(14) yes
O1 C1 C3 120.76(13) ?
O1 C1 C2 119.27(13) ?
C3 C1 C2 119.95(11) ?
N C2 C1 108.27(10) ?
N C2 C9 112.38(11) ?
C1 C2 C9 107.82(11) ?
N C2 H2 109.4 ?
C1 C2 H2 109.5 ?
C9 C2 H2 109.5 ?
C8 C3 C4 118.32(14) ?
C8 C3 C1 118.38(12) ?
C4 C3 C1 123.26(13) ?
C5 C4 C3 120.36(14) ?
C5 C4 H4 119.9 ?
C3 C4 H4 119.8 ?
C6 C5 C4 120.55(14) ?
C6 C5 H5 119.7 ?
C4 C5 H5 119.7 ?
C5 C6 C7 119.58(15) ?
C5 C6 H6 120.2 ?
C7 C6 H6 120.2 ?
C8 C7 C6 120.20(14) ?
C8 C7 H7 119.9 ?
C6 C7 H7 119.9 ?
C7 C8 C3 120.96(14) ?
C7 C8 H8 119.5 ?
C3 C8 H8 119.5 ?
C10 C9 C14 118.61(12) ?
C10 C9 C2 119.51(11) ?
C14 C9 C2 121.88(12) ?
C11 C10 C9 120.81(12) ?
C11 C10 H10 119.6 ?
C9 C10 H10 119.6 ?
C10 C11 C12 120.08(14) ?
C10 C11 H11 120.0 ?
C12 C11 H11 119.9 ?
C13 C12 C11 119.74(13) ?
C13 C12 H12 120.2 ?
C11 C12 H12 120.1 ?
C12 C13 C14 120.11(13) ?
C12 C13 H13 119.9 ?
C14 C13 H13 119.9 ?
C13 C14 C9 120.62(13) ?
C13 C14 H14 119.7 ?
C9 C14 H14 119.7 ?
N C15 C16 120.50(11) ?
N C15 C20 122.03(13) ?
C16 C15 C20 117.47(13) ?
C17 C16 C15 121.54(12) ?
C17 C16 H16 119.3 ?
C15 C16 H16 119.2 ?
C16 C17 C18 119.57(13) ?
C16 C17 H17 120.3 ?
C18 C17 H17 120.2 ?
C19 C18 C17 120.06(14) ?
C19 C18 Cl 119.46(10) ?
C17 C18 Cl 120.49(12) ?
C20 C19 C18 120.23(12) ?
C20 C19 H19 119.9 ?
C18 C19 H19 119.9 ?
C19 C20 C15 121.08(13) ?
C19 C20 H20 119.5 ?
C15 C20 H20 119.4 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
Cl C18 1.7453(16) ?
O1 C1 1.2237(16) yes
N C15 1.3718(19) yes
N C2 1.4423(18) yes
N H1 0.817(17) ?
C1 C3 1.487(2) yes
C1 C2 1.5375(19) yes
C2 C9 1.5389(18) ?
C2 H2 1.0000 ?
C3 C8 1.395(2) ?
C3 C4 1.4026(19) ?
C4 C5 1.385(2) ?
C4 H4 0.9500 ?
C5 C6 1.381(2) ?
C5 H5 0.9500 ?
C6 C7 1.389(2) ?
C6 H6 0.9500 ?
C7 C8 1.379(2) ?
C7 H7 0.9500 ?
C8 H8 0.9500 ?
C9 C10 1.393(2) ?
C9 C14 1.3937(18) ?
C10 C11 1.3858(19) ?
C10 H10 0.9501 ?
C11 C12 1.389(2) ?
C11 H11 0.9501 ?
C12 C13 1.383(2) ?
C12 H12 0.9499 ?
C13 C14 1.391(2) ?
C13 H13 0.9500 ?
C14 H14 0.9501 ?
C15 C16 1.4044(19) ?
C15 C20 1.4058(17) ?
C16 C17 1.382(2) ?
C16 H16 0.9499 ?
C17 C18 1.3923(18) ?
C17 H17 0.9500 ?
C18 C19 1.384(2) ?
C19 C20 1.382(2) ?
C19 H19 0.9500 ?
C20 H20 0.9501 ?
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 . 0.817(17) 2.238(19) 2.6259(17) 109.5(16) yes
N H1 O1 2_656 0.817(17) 2.756(18) 3.4791(15) 148.6(17) 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 -1.0(2) ?
C8 C3 C1 C2 -179.68(13) ?
C3 C1 C2 N -165.81(12) yes
C1 C2 N C15 178.20(12) yes
C2 N C15 C16 170.18(12) ?
O1 C1 C2 N 15.53(18) yes
C1 C2 C9 C10 65.65(16) ?
N C2 C9 C10 -53.58(17) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 222259
