#------------------------------------------------------------------------------
#$Date: 2017-10-13 03:48:21 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201957 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/01/12/2011239.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_2011239
loop_
_publ_author_name
'Jiménez-Cruz, Federico'
'Pérez-Caballero, Guadalupe'
'Hernández-Ortega, Simón'
'Rubio-Arroyo, Manuel'
_publ_section_title
;
 2-(4-Methoxyphenylazo)-4-phenylphenol
;
_journal_issue                   8
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              1028
_journal_page_last               1029
_journal_paper_doi               10.1107/S0108270100007307
_journal_volume                  56
_journal_year                    2000
_chemical_formula_sum            'C19 H16 N2 O2'
_chemical_formula_weight         304.34
_chemical_name_common            PCH3ON2
_chemical_name_systematic
;
 4-phenyl-2-[4-Methoxyphenyldiazenyl]phenol
;
_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'
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.48(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   6.449(2)
_cell_length_b                   8.638(2)
_cell_length_c                   28.414(17)
_cell_measurement_reflns_used    49
_cell_measurement_temperature    273(2)
_cell_measurement_theta_max      24.5
_cell_measurement_theta_min      4.9
_cell_volume                     1582.8(11)
_computing_cell_refinement       XSCANS
_computing_data_collection       'XSCANS (Siemens, 1994)'
_computing_data_reduction        XSCANS
_computing_molecular_graphics    SHELXTL/PC
_computing_publication_material  SHELXL97
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXTL/PC (Sheldrick, 1990)'
_diffrn_ambient_temperature      273(2)
_diffrn_measured_fraction_theta_full .932
_diffrn_measured_fraction_theta_max .932
_diffrn_measurement_device_type  'Siemens P4/PC'
_diffrn_measurement_method       ω-2θ
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     .71073
_diffrn_reflns_av_R_equivalents  .0453
_diffrn_reflns_av_sigmaI/netI    .0857
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_number            3062
_diffrn_reflns_theta_full        25.0
_diffrn_reflns_theta_max         25.0
_diffrn_reflns_theta_min         2.46
_diffrn_standards_decay_%        <2
_diffrn_standards_interval_count 97
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    .084
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            Red
_exptl_crystal_density_diffrn    1.277
_exptl_crystal_density_method    none
_exptl_crystal_description       Prism
_exptl_crystal_F_000             640
_exptl_crystal_size_max          .40
_exptl_crystal_size_mid          .24
_exptl_crystal_size_min          .20
_refine_diff_density_max         .11
_refine_diff_density_min         -.20
_refine_ls_extinction_coef       .0102(11)
_refine_ls_extinction_method     'SHELXL97 (Sheldrick, 1997)'
_refine_ls_goodness_of_fit_ref   .767
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     212
_refine_ls_number_reflns         2794
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      .767
_refine_ls_R_factor_all          .1232
_refine_ls_R_factor_gt           .0482
_refine_ls_shift/su_max          <0.001
_refine_ls_shift/su_mean         .000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[s²(Fo²)+(0.0488P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         .1268
_reflns_number_gt                1126
_reflns_number_total             2794
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            ob1031.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 

The following automatic conversions were performed:

'_refine_ls_weighting_scheme' value 'calc w =
1/[s^2^(Fo^2^)+(0.0488P)^2^] where P=(Fo^2^+2Fc^2^)/3' was changed to
'calc'. New tag '_refine_ls_weighting_details' was created. The value
of the new tag was set to 'w = 1/[s^2^(Fo^2^)+(0.0488P)^2^] where
P=(Fo^2^+2Fc^2^)/3'.

Automatic conversion script
Id: cif_fix_values 3143 2015-03-26 13:38:13Z robertas 
;
_cod_original_cell_volume        1582.90(10)
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               2011239
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_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
_atom_site_type_symbol
O1 .4701(4) 1.0730(3) .09940(8) .0816(8) Uani d . 1 . . O
H1 .397(5) 1.027(4) .0774(10) .060 Uiso d . 1 . . H
O2 -.1259(4) .5901(3) -.09131(8) .0879(8) Uani d . 1 . . O
N1 .1696(4) .9116(3) .06438(8) .0623(7) Uani d . 1 . . N
N2 .0578(4) .9241(3) .10099(8) .0621(7) Uani d . 1 . . N
C1 .0790(5) .8262(4) .02666(9) .0564(8) Uani d . 1 . . C
C2 -.1168(5) .7605(4) .02715(10) .0687(9) Uani d . 1 . . C
H2 -.1991 .7703 .0537 .060 Uiso calc R 1 . . H
C3 -.1895(5) .6814(4) -.01111(11) .0687(9) Uani d . 1 . . C
H3 -.3212 .6376 -.0104 .060 Uiso calc R 1 . . H
C4 -.0688(5) .6657(4) -.05120(10) .0668(9) Uani d . 1 . . C
C5 .1256(5) .7332(4) -.05185(11) .0721(10) Uani d . 1 . . C
H5 .2063 .7247 -.0787 .060 Uiso calc R 1 . . H
C6 .2014(5) .8126(4) -.01349(10) .0664(9) Uani d . 1 . . C
H6 .3328 .8568 -.0142 .060 Uiso calc R 1 . . H
C7 -.3243(6) .5205(5) -.09392(13) .0967(13) Uani d . 1 . . C
H7A -.3265 .4300 -.0743 .060 Uiso calc R 1 . . H
H7B -.3540 .4915 -.1259 .060 Uiso calc R 1 . . H
H7C -.4270 .5927 -.0833 .060 Uiso calc R 1 . . H
C11 .3472(5) 1.0766(4) .13804(11) .0639(9) Uani d . 1 . . C
C12 .1504(5) 1.0073(4) .13833(10) .0564(8) Uani d . 1 . . C
C13 .0320(5) 1.0171(4) .17951(10) .0591(8) Uani d . 1 . . C
H13 -.0989 .9720 .1796 .060 Uiso calc R 1 . . H
C14 .1008(5) 1.0906(4) .21970(10) .0581(8) Uani d . 1 . . C
C15 .3002(5) 1.1555(4) .21825(11) .0681(9) Uani d . 1 . . C
H15 .3539 1.2031 .2451 .060 Uiso calc R 1 . . H
C16 .4183(5) 1.1504(4) .17804(11) .0737(10) Uani d . 1 . . C
H16 .5480 1.1975 .1779 .060 Uiso calc R 1 . . H
C17 -.0285(5) 1.0970(4) .26296(9) .0539(7) Uani d . 1 . . C
C18 -.1834(5) .9885(4) .27078(10) .0655(9) Uani d . 1 . . C
H18 -.2033 .9091 .2491 .060 Uiso calc R 1 . . H
C19 -.3089(5) .9953(4) .31004(11) .0731(10) Uani d . 1 . . C
H19 -.4110 .9208 .3146 .060 Uiso calc R 1 . . H
C20 -.2823(5) 1.1124(4) .34225(11) .0713(9) Uani d . 1 . . C
H20 -.3674 1.1181 .3685 .060 Uiso calc R 1 . . H
C21 -.1304(6) 1.2205(4) .33565(11) .0700(10) Uani d . 1 . . C
H21 -.1110 1.2990 .3577 .060 Uiso calc R 1 . . H
C22 -.0048(5) 1.2138(4) .29625(10) .0635(9) Uani d . 1 . . C
H22 .0969 1.2887 .2920 .060 Uiso calc R 1 . . H
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C .0033 .0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H .0000 .0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N .0061 .0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O .0106 .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
C11 O1 H1 106(2) no
C4 O2 C7 119.2(3) no
N2 N1 C1 115.4(3) yes
N1 N2 C12 114.7(3) yes
C2 C1 C6 119.7(3) no
C2 C1 N1 124.8(3) yes
C6 C1 N1 115.4(3) yes
C3 C2 C1 120.2(3) no
C3 C2 H2 119.9 no
C1 C2 H2 119.9 no
C2 C3 C4 120.7(3) no
C2 C3 H3 119.6 no
C4 C3 H3 119.6 no
O2 C4 C5 115.6(3) yes
O2 C4 C3 125.6(3) yes
C5 C4 C3 118.8(3) no
C6 C5 C4 121.3(3) no
C6 C5 H5 119.4 no
C4 C5 H5 119.4 no
C5 C6 C1 119.2(3) no
C5 C6 H6 120.4 no
C1 C6 H6 120.4 no
O2 C7 H7A 109.5 no
O2 C7 H7B 109.5 no
H7A C7 H7B 109.5 no
O2 C7 H7C 109.5 no
H7A C7 H7C 109.5 no
H7B C7 H7C 109.5 no
O1 C11 C16 118.8(3) yes
O1 C11 C12 121.8(3) yes
C16 C11 C12 119.3(3) no
C11 C12 C13 118.4(3) no
C11 C12 N2 126.3(3) yes
C13 C12 N2 115.3(3) yes
C14 C13 C12 123.1(3) no
C14 C13 H13 118.4 no
C12 C13 H13 118.4 no
C13 C14 C15 116.5(3) no
C13 C14 C17 121.5(3) no
C15 C14 C17 121.9(3) no
C16 C15 C14 121.7(3) no
C16 C15 H15 119.2 no
C14 C15 H15 119.2 no
C11 C16 C15 120.9(3) no
C11 C16 H16 119.5 no
C15 C16 H16 119.5 no
C18 C17 C22 117.2(3) no
C18 C17 C14 120.9(3) no
C22 C17 C14 121.9(3) no
C19 C18 C17 121.7(3) no
C19 C18 H18 119.2 no
C17 C18 H18 119.2 no
C20 C19 C18 119.9(4) no
C20 C19 H19 120.1 no
C18 C19 H19 120.1 no
C21 C20 C19 119.8(3) no
C21 C20 H20 120.1 no
C19 C20 H20 120.1 no
C20 C21 C22 120.3(3) no
C20 C21 H21 119.9 no
C22 C21 H21 119.9 no
C21 C22 C17 121.2(3) no
C21 C22 H22 119.4 no
C17 C22 H22 119.4 no
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 C11 . 1.361(4) yes
O1 H1 . .87(3) no
O2 C4 . 1.360(4) yes
O2 C7 . 1.414(4) yes
N1 N2 . 1.275(3) yes
N1 C1 . 1.423(4) yes
N2 C12 . 1.409(4) yes
C1 C2 . 1.385(4) no
C1 C6 . 1.398(4) no
C2 C3 . 1.365(4) no
C2 H2 . .9300 no
C3 C4 . 1.392(4) no
C3 H3 . .9300 no
C4 C5 . 1.382(5) no
C5 C6 . 1.373(4) no
C5 H5 . .9300 no
C6 H6 . .9300 no
C7 H7A . .9600 no
C7 H7B . .9600 no
C7 H7C . .9600 no
C11 C16 . 1.377(4) no
C11 C12 . 1.403(4) no
C12 C13 . 1.405(4) no
C13 C14 . 1.377(4) no
C13 H13 . .9300 no
C14 C15 . 1.405(4) no
C14 C17 . 1.492(4) no
C15 C16 . 1.379(4) no
C15 H15 . .9300 no
C16 H16 . .9300 no
C17 C18 . 1.389(4) no
C17 C22 . 1.391(4) no
C18 C19 . 1.384(4) no
C18 H18 . .9300 no
C19 C20 . 1.374(5) no
C19 H19 . .9300 no
C20 C21 . 1.369(5) no
C20 H20 . .9300 no
C21 C22 . 1.388(5) no
C21 H21 . .9300 no
C22 H22 . .9300 no
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
O1 H1 N1 .88(3) 1.81(3) 2.581(4) 146(3) yes
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 12554746
