#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/05/2220531.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_2220531
loop_
_publ_author_name
'Krzymiński, Karol'
'Wera, Michał'
'Sikorski, Artur'
'Błażejowski, Jerzy'
_publ_section_title
;
 4-Methoxy-N-phenylaniline
;
_journal_coeditor_code           HK2570
_journal_issue                   1
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o152
_journal_paper_doi               10.1107/S1600536808039457
_journal_volume                  65
_journal_year                    2009
_chemical_formula_iupac          'C13 H13 N O'
_chemical_formula_moiety         'C13 H13 N O'
_chemical_formula_sum            'C13 H13 N O'
_chemical_formula_weight         199.24
_chemical_name_systematic
;
4-Methoxy-N-phenylaniline
;
_space_group_IT_number           56
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2ab 2ac'
_symmetry_space_group_name_H-M   'P c c n'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   15.090(3)
_cell_length_b                   18.394(4)
_cell_length_c                   7.596(2)
_cell_measurement_reflns_used    50
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      25
_cell_measurement_theta_min      2.21
_cell_volume                     2108.4(8)
_computing_cell_refinement       'KM-4 Software (Oxford Diffraction, 2003)'
_computing_data_collection       'KM-4 Software (Oxford Diffraction, 2003)'
_computing_data_reduction        'KM-4 Software (Oxford Diffraction, 2003)'
_computing_molecular_graphics    'ORTEPII (Johnson, 1976)'
_computing_publication_material
'SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2003)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      295(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Kuma KM-4'
_diffrn_measurement_method       θ/2θ
_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  0.0347
_diffrn_reflns_av_sigmaI/netI    0.0496
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       0
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       2
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            2443
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         2.21
_diffrn_standards_decay_%        0.47
_diffrn_standards_interval_count 200
_diffrn_standards_number         3
_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       block
_exptl_crystal_F_000             848
_exptl_crystal_size_max          0.05
_exptl_crystal_size_mid          0.03
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.162
_refine_diff_density_min         -0.153
_refine_ls_extinction_coef       0.015(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL97 (Sheldrick, 2008)'
_refine_ls_goodness_of_fit_ref   0.992
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     138
_refine_ls_number_reflns         1851
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.992
_refine_ls_R_factor_all          0.1104
_refine_ls_R_factor_gt           0.0444
_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)+(0.081P)²+0.0542P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1053
_refine_ls_wR_factor_ref         0.1306
_reflns_number_gt                1005
_reflns_number_total             1851
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            hk2570.cif
_cod_data_source_block           I
_cod_database_code               2220531
_cod_database_fobs_code          2220531
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y+1/2, z'
'-x, y+1/2, -z+1/2'
'x+1/2, -y, -z+1/2'
'-x, -y, -z'
'x-1/2, y-1/2, -z'
'x, -y-1/2, z-1/2'
'-x-1/2, y, 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
C C1 0.49051(14) 0.32843(9) 0.6655(3) 0.0526(6) Uani d . 1 . .
C C2 0.52660(14) 0.36650(10) 0.8048(3) 0.0533(5) Uani d . 1 . .
H H2 0.5861 0.3794 0.8010 0.064 Uiso calc R 1 . .
C C3 0.47688(12) 0.38576(10) 0.9489(3) 0.0500(5) Uani d . 1 . .
H H3 0.5025 0.4117 1.0409 0.060 Uiso calc R 1 . .
C C4 0.38875(13) 0.36634(10) 0.9558(3) 0.0491(5) Uani d . 1 . .
C C5 0.35215(14) 0.32732(10) 0.8191(3) 0.0553(6) Uani d . 1 . .
H H5 0.2930 0.3133 0.8244 0.066 Uiso calc R 1 . .
C C6 0.40192(15) 0.30921(10) 0.6763(3) 0.0577(6) Uani d . 1 . .
H H6 0.3760 0.2835 0.5843 0.069 Uiso calc R 1 . .
N N7 0.54179(14) 0.30655(9) 0.5208(2) 0.0679(6) Uani d . 1 . .
H H7 0.5415 0.2610 0.4954 0.082 Uiso calc R 1 . .
C C8 0.59269(13) 0.35133(11) 0.4155(3) 0.0488(5) Uani d . 1 . .
C C9 0.59081(13) 0.42662(10) 0.4292(3) 0.0535(5) Uani d . 1 . .
H H9 0.5561 0.4486 0.5153 0.064 Uiso calc R 1 . .
C C10 0.63953(16) 0.46850(13) 0.3170(3) 0.0701(7) Uani d . 1 . .
H H10 0.6377 0.5188 0.3279 0.084 Uiso calc R 1 . .
C C11 0.69087(19) 0.43785(18) 0.1892(3) 0.0882(9) Uani d . 1 . .
H H11 0.7233 0.4669 0.1124 0.106 Uiso calc R 1 . .
C C12 0.69399(16) 0.36363(17) 0.1759(3) 0.0809(8) Uani d . 1 . .
H H12 0.7291 0.3422 0.0897 0.097 Uiso calc R 1 . .
C C13 0.64619(14) 0.32079(13) 0.2877(3) 0.0633(6) Uani d . 1 . .
H H13 0.6497 0.2705 0.2777 0.076 Uiso calc R 1 . .
O O14 0.33254(9) 0.38212(8) 1.0914(2) 0.0671(5) Uani d . 1 . .
C C15 0.36725(18) 0.41960(15) 1.2379(3) 0.0809(7) Uani d . 1 . .
H H15A 0.3220 0.4246 1.3260 0.121 Uiso calc R 1 . .
H H15B 0.3871 0.4669 1.2018 0.121 Uiso calc R 1 . .
H H15C 0.4162 0.3928 1.2857 0.121 Uiso calc 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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C2 C1 C6 . . 117.68(19) ?
C2 C1 N7 . . 121.9(2) ?
C6 C1 N7 . . 120.36(19) ?
C3 C2 C1 . . 121.74(19) ?
C3 C2 H2 . . 119.1 ?
C1 C2 H2 . . 119.1 ?
C2 C3 C4 . . 119.42(19) ?
C2 C3 H3 . . 120.3 ?
C4 C3 H3 . . 120.3 ?
O14 C4 C3 . . 125.00(18) ?
O14 C4 C5 . . 115.48(17) ?
C3 C4 C5 . . 119.52(19) ?
C6 C5 C4 . . 120.48(18) ?
C6 C5 H5 . . 119.8 ?
C4 C5 H5 . . 119.8 ?
C5 C6 C1 . . 121.15(19) ?
C5 C6 H6 . . 119.4 ?
C1 C6 H6 . . 119.4 ?
C1 N7 C8 . . 126.1(2) ?
C8 N7 H7 . . 116.9 ?
C1 N7 H7 . . 116.9 ?
N7 C8 C13 . . 119.30(19) ?
N7 C8 C9 . . 122.67(18) ?
C13 C8 C9 . . 118.0(2) ?
C10 C9 C8 . . 120.4(2) ?
C10 C9 H9 . . 119.8 ?
C8 C9 H9 . . 119.8 ?
C9 C10 C11 . . 121.1(2) ?
C9 C10 H10 . . 119.4 ?
C11 C10 H10 . . 119.4 ?
C10 C11 C12 . . 119.0(2) ?
C10 C11 H11 . . 120.5 ?
C12 C11 H11 . . 120.5 ?
C13 C12 C11 . . 120.8(2) ?
C13 C12 H12 . . 119.6 ?
C11 C12 H12 . . 119.6 ?
C12 C13 C8 . . 120.7(2) ?
C12 C13 H13 . . 119.6 ?
C8 C13 H13 . . 119.6 ?
C4 O14 C15 . . 117.9(2) ?
O14 C15 H15A . . 109.5 ?
O14 C15 H15B . . 109.5 ?
H15A C15 H15B . . 109.5 ?
O14 C15 H15C . . 109.5 ?
H15A C15 H15C . . 109.5 ?
H15B C15 H15C . . 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
C1 C2 . 1.381(3) ?
C1 C6 . 1.385(3) ?
C1 N7 . 1.403(3) ?
C2 C3 . 1.373(3) ?
C2 H2 . 0.9300 ?
C3 C4 . 1.378(3) ?
C3 H3 . 0.9300 ?
C4 O14 . 1.365(2) ?
C4 C5 . 1.378(3) ?
C5 C6 . 1.361(3) ?
C5 H5 . 0.9300 ?
C6 H6 . 0.9300 ?
N7 C8 . 1.381(3) ?
N7 H7 . 0.8600 ?
C8 C13 . 1.382(3) ?
C8 C9 . 1.389(3) ?
C9 C10 . 1.364(3) ?
C9 H9 . 0.9300 ?
C10 C11 . 1.364(4) ?
C10 H10 . 0.9300 ?
C11 C12 . 1.370(4) ?
C11 H11 . 0.9300 ?
C12 C13 . 1.365(3) ?
C12 H12 . 0.9300 ?
C13 H13 . 0.9300 ?
O14 C15 . 1.410(3) ?
C15 H15A . 0.9600 ?
C15 H15B . 0.9600 ?
C15 H15C . 0.9600 ?
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
C3 H3 Cg2 1_556 0.93 2.91 3.671(2) 139
N7 H7 Cg1 7_565 0.86 2.88 3.593(2) 142
C10 H10 Cg1 5_666 0.93 2.92 3.723(3) 145
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 . . . . -0.8(3) ?
N7 C1 C2 C3 . . . . -177.82(17) ?
C1 C2 C3 C4 . . . . 0.4(3) ?
C2 C3 C4 O14 . . . . 179.92(17) ?
C2 C3 C4 C5 . . . . 0.6(3) ?
O14 C4 C5 C6 . . . . 179.34(17) ?
C3 C4 C5 C6 . . . . -1.3(3) ?
C4 C5 C6 C1 . . . . 0.9(3) ?
C2 C1 C6 C5 . . . . 0.1(3) ?
N7 C1 C6 C5 . . . . 177.18(18) ?
C2 C1 N7 C8 . . . . -55.5(3) ?
C6 C1 N7 C8 . . . . 127.6(2) ?
C1 N7 C8 C13 . . . . 174.0(2) ?
C1 N7 C8 C9 . . . . -7.8(3) ?
N7 C8 C9 C10 . . . . -177.21(19) ?
C13 C8 C9 C10 . . . . 1.1(3) ?
C8 C9 C10 C11 . . . . 0.1(3) ?
C9 C10 C11 C12 . . . . -0.9(4) ?
C10 C11 C12 C13 . . . . 0.4(4) ?
C11 C12 C13 C8 . . . . 0.8(4) ?
N7 C8 C13 C12 . . . . 176.8(2) ?
C9 C8 C13 C12 . . . . -1.5(3) ?
C3 C4 O14 C15 . . . . -1.6(3) ?
C5 C4 O14 C15 . . . . 177.7(2) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 13920
