#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/17/2221736.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_2221736
loop_
_publ_author_name
'Huang, Kun'
'Huang, Feng'
'Qin, Da-Bin'
_publ_section_title
;
 N-(2-Aminophenyl)-2-anilinobenzamide
;
_journal_coeditor_code           IM2107
_journal_issue                   5
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1108
_journal_paper_doi               10.1107/S1600536809013014
_journal_volume                  65
_journal_year                    2009
_chemical_formula_iupac          'C19 H17 N3 O'
_chemical_formula_moiety         'C19 H17 N3 O'
_chemical_formula_sum            'C19 H17 N3 O'
_chemical_formula_weight         303.36
_chemical_name_systematic
;
N-(2-Aminophenyl)-2-anilinobenzamide
;
_space_group_IT_number           9
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'C -2yc'
_symmetry_space_group_name_H-M   'C 1 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                 103.398(7)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   6.707(3)
_cell_length_b                   25.950(10)
_cell_length_c                   9.480(5)
_cell_measurement_reflns_used    2858
_cell_measurement_temperature    93(2)
_cell_measurement_theta_max      27.54
_cell_measurement_theta_min      3.14
_cell_volume                     1605.1(13)
_computing_cell_refinement       'RAPID-AUTO (Rigaku/MSC, 2004)'
_computing_data_collection       'RAPID-AUTO (Rigaku/MSC, 2004)'
_computing_data_reduction        'RAPID-AUTO (Rigaku/MSC, 2004)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      93(2)
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'Rigaku Spider'
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Rotating Anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0291
_diffrn_reflns_av_sigmaI/netI    0.0344
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       31
_diffrn_reflns_limit_k_min       -33
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            6515
_diffrn_reflns_theta_full        27.54
_diffrn_reflns_theta_max         27.54
_diffrn_reflns_theta_min         3.14
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.080
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.255
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Platelet
_exptl_crystal_F_000             640
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.27
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.140
_refine_diff_density_min         -0.152
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.001
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     224
_refine_ls_number_reflns         1844
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.001
_refine_ls_R_factor_all          0.0387
_refine_ls_R_factor_gt           0.0348
_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)+(0.0376P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0696
_refine_ls_wR_factor_ref         0.0720
_reflns_number_gt                1695
_reflns_number_total             1844
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            im2107.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 

The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_cell_volume        1605.0(14)
_cod_original_sg_symbol_H-M      'C c'
_cod_database_code               2221736
_cod_database_fobs_code          2221736
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'x, -y, z+1/2'
'x+1/2, y+1/2, 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
_atom_site_disorder_assembly
_atom_site_disorder_group
O O1 0.4009(2) 0.47225(5) 0.56166(13) 0.0295(3) Uani d . 1 . .
N N2 0.3896(2) 0.51617(6) 0.35407(16) 0.0257(3) Uani d . 1 . .
N N1 0.4426(3) 0.36962(7) 0.52152(19) 0.0368(4) Uani d . 1 . .
N N3 0.0087(3) 0.53595(9) 0.16236(19) 0.0418(5) Uani d . 1 . .
H H3A 0.106(4) 0.5228(9) 0.121(3) 0.053(7) Uiso d . 1 . .
H H3B -0.103(4) 0.5495(10) 0.097(3) 0.063(8) Uiso d . 1 . .
C C1 0.3021(4) 0.28921(8) 0.3998(2) 0.0435(6) Uani d . 1 . .
H H1 0.3647 0.2955 0.3212 0.052 Uiso calc R 1 . .
C C2 0.1803(4) 0.24613(9) 0.3980(3) 0.0600(7) Uani d . 1 . .
H H2 0.1605 0.2230 0.3183 0.072 Uiso calc R 1 . .
C C3 0.0878(5) 0.23638(10) 0.5100(4) 0.0725(9) Uani d . 1 . .
H H3 0.0028 0.2070 0.5080 0.087 Uiso calc R 1 . .
C C4 0.1209(5) 0.27031(10) 0.6262(4) 0.0674(8) Uani d . 1 . .
H H4 0.0588 0.2638 0.7049 0.081 Uiso calc R 1 . .
C C5 0.2422(4) 0.31325(9) 0.6295(3) 0.0470(6) Uani d . 1 . .
H H5 0.2633 0.3360 0.7100 0.056 Uiso calc R 1 . .
C C6 0.3335(3) 0.32336(8) 0.5156(2) 0.0366(5) Uani d . 1 . .
C C7 0.5729(3) 0.38514(8) 0.4348(2) 0.0326(5) Uani d . 1 . .
C C8 0.7016(3) 0.34982(9) 0.3887(2) 0.0425(5) Uani d . 1 . .
H H8 0.6954 0.3144 0.4127 0.051 Uiso calc R 1 . .
C C9 0.8377(4) 0.36594(10) 0.3087(2) 0.0475(6) Uani d . 1 . .
H H9 0.9231 0.3413 0.2773 0.057 Uiso calc R 1 . .
C C10 0.8519(3) 0.41732(10) 0.2733(2) 0.0429(6) Uani d . 1 . .
H H10 0.9467 0.4281 0.2187 0.052 Uiso calc R 1 . .
C C11 0.7264(3) 0.45261(9) 0.3184(2) 0.0331(5) Uani d . 1 . .
H H11 0.7366 0.4880 0.2952 0.040 Uiso calc R 1 . .
C C12 0.5841(3) 0.43752(8) 0.39754(18) 0.0271(4) Uani d . 1 . .
C C13 0.4524(3) 0.47661(7) 0.44460(18) 0.0245(4) Uani d . 1 . .
C C14 0.2603(3) 0.55640(7) 0.38352(19) 0.0272(4) Uani d . 1 . .
C C15 0.3209(3) 0.58570(8) 0.5089(2) 0.0324(4) Uani d . 1 . .
H H15 0.4505 0.5797 0.5728 0.039 Uiso calc R 1 . .
C C16 0.1931(4) 0.62359(9) 0.5410(2) 0.0420(5) Uani d . 1 . .
H H16 0.2341 0.6435 0.6269 0.050 Uiso calc R 1 . .
C C17 0.0059(4) 0.63226(10) 0.4473(2) 0.0492(6) Uani d . 1 . .
H H17 -0.0831 0.6579 0.4697 0.059 Uiso calc R 1 . .
C C18 -0.0532(4) 0.60405(10) 0.3216(2) 0.0468(6) Uani d . 1 . .
H H18 -0.1821 0.6108 0.2577 0.056 Uiso calc R 1 . .
C C19 0.0727(3) 0.56574(8) 0.2863(2) 0.0339(5) Uani d . 1 . .
H H1N 0.400(4) 0.3966(10) 0.563(3) 0.053(7) Uiso d . 1 . .
H H2N 0.414(3) 0.5148(7) 0.269(2) 0.030(5) Uiso d . 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 0.0000 '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 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0000 '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
C13 N2 C14 . . 123.37(15) ?
C13 N2 H2N . . 118.0(13) ?
C14 N2 H2N . . 118.0(13) ?
C7 N1 C6 . . 128.24(19) ?
C7 N1 H1N . . 110.2(17) ?
C6 N1 H1N . . 118.5(17) ?
C19 N3 H3A . . 117.9(16) ?
C19 N3 H3B . . 113.5(16) ?
H3A N3 H3B . . 114(2) ?
C2 C1 C6 . . 120.4(2) ?
C2 C1 H1 . . 119.8 ?
C6 C1 H1 . . 119.8 ?
C3 C2 C1 . . 120.8(3) ?
C3 C2 H2 . . 119.6 ?
C1 C2 H2 . . 119.6 ?
C2 C3 C4 . . 118.7(3) ?
C2 C3 H3 . . 120.7 ?
C4 C3 H3 . . 120.7 ?
C5 C4 C3 . . 121.1(3) ?
C5 C4 H4 . . 119.4 ?
C3 C4 H4 . . 119.4 ?
C4 C5 C6 . . 120.1(3) ?
C4 C5 H5 . . 119.9 ?
C6 C5 H5 . . 119.9 ?
C5 C6 C1 . . 118.9(2) ?
C5 C6 N1 . . 116.9(2) ?
C1 C6 N1 . . 124.09(19) ?
N1 C7 C8 . . 120.88(19) ?
N1 C7 C12 . . 120.29(18) ?
C8 C7 C12 . . 118.77(19) ?
C9 C8 C7 . . 120.6(2) ?
C9 C8 H8 . . 119.7 ?
C7 C8 H8 . . 119.7 ?
C8 C9 C10 . . 121.1(2) ?
C8 C9 H9 . . 119.4 ?
C10 C9 H9 . . 119.4 ?
C11 C10 C9 . . 119.0(2) ?
C11 C10 H10 . . 120.5 ?
C9 C10 H10 . . 120.5 ?
C10 C11 C12 . . 121.5(2) ?
C10 C11 H11 . . 119.3 ?
C12 C11 H11 . . 119.3 ?
C11 C12 C7 . . 119.10(18) ?
C11 C12 C13 . . 119.91(18) ?
C7 C12 C13 . . 120.96(17) ?
O1 C13 N2 . . 122.03(17) ?
O1 C13 C12 . . 121.07(17) ?
N2 C13 C12 . . 116.89(15) ?
C15 C14 C19 . . 120.58(18) ?
C15 C14 N2 . . 119.84(17) ?
C19 C14 N2 . . 119.57(17) ?
C16 C15 C14 . . 120.2(2) ?
C16 C15 H15 . . 119.9 ?
C14 C15 H15 . . 119.9 ?
C17 C16 C15 . . 119.5(2) ?
C17 C16 H16 . . 120.2 ?
C15 C16 H16 . . 120.2 ?
C18 C17 C16 . . 120.5(2) ?
C18 C17 H17 . . 119.8 ?
C16 C17 H17 . . 119.8 ?
C17 C18 C19 . . 121.2(2) ?
C17 C18 H18 . . 119.4 ?
C19 C18 H18 . . 119.4 ?
N3 C19 C18 . . 120.96(19) ?
N3 C19 C14 . . 121.04(19) ?
C18 C19 C14 . . 117.92(19) ?
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 C13 . 1.241(2) ?
N2 C13 . 1.342(2) ?
N2 C14 . 1.425(2) ?
N2 H2N . 0.86(2) ?
N1 C7 . 1.391(3) ?
N1 C6 . 1.400(3) ?
N1 H1N . 0.88(3) ?
N3 C19 . 1.389(3) ?
N3 H3A . 0.90(3) ?
N3 H3B . 0.93(3) ?
C1 C2 . 1.382(4) ?
C1 C6 . 1.389(3) ?
C1 H1 . 0.9500 ?
C2 C3 . 1.372(4) ?
C2 H2 . 0.9500 ?
C3 C4 . 1.387(4) ?
C3 H3 . 0.9500 ?
C4 C5 . 1.376(4) ?
C4 H4 . 0.9500 ?
C5 C6 . 1.383(3) ?
C5 H5 . 0.9500 ?
C7 C8 . 1.397(3) ?
C7 C12 . 1.411(3) ?
C8 C9 . 1.380(3) ?
C8 H8 . 0.9500 ?
C9 C10 . 1.384(4) ?
C9 H9 . 0.9500 ?
C10 C11 . 1.377(3) ?
C10 H10 . 0.9500 ?
C11 C12 . 1.400(3) ?
C11 H11 . 0.9500 ?
C12 C13 . 1.480(2) ?
C14 C15 . 1.390(3) ?
C14 C19 . 1.398(3) ?
C15 C16 . 1.384(3) ?
C15 H15 . 0.9500 ?
C16 C17 . 1.378(3) ?
C16 H16 . 0.9500 ?
C17 C18 . 1.376(4) ?
C17 H17 . 0.9500 ?
C18 C19 . 1.394(3) ?
C18 H18 . 0.9500 ?
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 . 0.88(3) 1.96(3) 2.714(3) 142(2)
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 . . . . 0.2(4) ?
C1 C2 C3 C4 . . . . -0.8(4) ?
C2 C3 C4 C5 . . . . 0.6(4) ?
C3 C4 C5 C6 . . . . 0.1(4) ?
C4 C5 C6 C1 . . . . -0.7(4) ?
C4 C5 C6 N1 . . . . 175.5(2) ?
C2 C1 C6 C5 . . . . 0.5(3) ?
C2 C1 C6 N1 . . . . -175.4(2) ?
C7 N1 C6 C5 . . . . 169.1(2) ?
C7 N1 C6 C1 . . . . -14.9(3) ?
C6 N1 C7 C8 . . . . -37.1(3) ?
C6 N1 C7 C12 . . . . 145.9(2) ?
N1 C7 C8 C9 . . . . -176.8(2) ?
C12 C7 C8 C9 . . . . 0.2(3) ?
C7 C8 C9 C10 . . . . 0.7(3) ?
C8 C9 C10 C11 . . . . -0.5(3) ?
C9 C10 C11 C12 . . . . -0.7(3) ?
C10 C11 C12 C7 . . . . 1.6(3) ?
C10 C11 C12 C13 . . . . 179.76(18) ?
N1 C7 C12 C11 . . . . 175.75(17) ?
C8 C7 C12 C11 . . . . -1.3(3) ?
N1 C7 C12 C13 . . . . -2.4(3) ?
C8 C7 C12 C13 . . . . -179.51(17) ?
C14 N2 C13 O1 . . . . 0.2(3) ?
C14 N2 C13 C12 . . . . 179.19(17) ?
C11 C12 C13 O1 . . . . -145.63(18) ?
C7 C12 C13 O1 . . . . 32.5(3) ?
C11 C12 C13 N2 . . . . 35.3(2) ?
C7 C12 C13 N2 . . . . -146.50(18) ?
C13 N2 C14 C15 . . . . 57.6(2) ?
C13 N2 C14 C19 . . . . -121.91(19) ?
C19 C14 C15 C16 . . . . 1.8(3) ?
N2 C14 C15 C16 . . . . -177.67(18) ?
C14 C15 C16 C17 . . . . -0.4(3) ?
C15 C16 C17 C18 . . . . -0.9(3) ?
C16 C17 C18 C19 . . . . 0.7(3) ?
C17 C18 C19 N3 . . . . 177.3(2) ?
C17 C18 C19 C14 . . . . 0.7(3) ?
C15 C14 C19 N3 . . . . -178.58(18) ?
N2 C14 C19 N3 . . . . 0.9(3) ?
C15 C14 C19 C18 . . . . -2.0(3) ?
N2 C14 C19 C18 . . . . 177.54(18) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 24742143
