#------------------------------------------------------------------------------
#$Date: 2017-10-13 09:09:21 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201973 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/20/07/2200729.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_2200729
loop_
_publ_author_name
'Oleg Ya. Borbulevych'
'Mikhail Yu. Antipin'
_publ_section_title
;Redetermination of
 N,N-dimethyl-N-{4-[(E)-(4-methyl-3-nitrophenyl)diazenyl]phenyl}amine
 at 193 K: another example of dynamic disorder of substituted azobenzene
 compounds
;
_journal_issue                   12
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1250
_journal_page_last               o1251
_journal_paper_doi               10.1107/S1600536801020128
_journal_volume                  57
_journal_year                    2001
_chemical_formula_iupac          'C15 H16 N4 O2'
_chemical_formula_moiety         'C15 H16 N4 O2'
_chemical_formula_sum            'C15 H16 N4 O2'
_chemical_formula_weight         284.32
_chemical_name_systematic
;
N,N-dimethyl-N-{4-[(E)-(4-methyl-3-nitrophenyl)diazenyl]phenyl}amine
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 107.26(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.509(6)
_cell_length_b                   10.763(5)
_cell_length_c                   13.146(7)
_cell_measurement_reflns_used    24
_cell_measurement_temperature    193(2)
_cell_measurement_theta_max      11
_cell_measurement_theta_min      10
_cell_volume                     1420.0(13)
_computing_cell_refinement       P3
_computing_data_collection       'P3 (Siemens, 1989)'
_computing_data_reduction        'XDISK  (Siemens, 1991)'
_computing_molecular_graphics    'SHELXTL97 (Sheldrick, 1997)'
_computing_publication_material  SHELXTL97
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      193(2)
_diffrn_measured_fraction_theta_full .974
_diffrn_measured_fraction_theta_max .974
_diffrn_measurement_device_type  'Syntex P2₁/PC'
_diffrn_measurement_method       θ/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  .0494
_diffrn_reflns_av_sigmaI/netI    .0927
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            2591
_diffrn_reflns_theta_full        25.06
_diffrn_reflns_theta_max         25.06
_diffrn_reflns_theta_min         2.03
_diffrn_standards_decay_%        3.7
_diffrn_standards_interval_count 98
_diffrn_standards_number         2
_exptl_absorpt_coefficient_mu    .092
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.330
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             600
_exptl_crystal_size_max          .40
_exptl_crystal_size_mid          .20
_exptl_crystal_size_min          .20
_refine_diff_density_max         .246
_refine_diff_density_min         -.190
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   .867
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     193
_refine_ls_number_reflns         2447
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      .867
_refine_ls_R_factor_all          .1329
_refine_ls_R_factor_gt           .0550
_refine_ls_shift/su_max          <0.001
_refine_ls_shift/su_mean         .000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w = 1/[σ²(Fo²)+(0.0998P)²] where P = (Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         .1544
_reflns_number_gt                1229
_reflns_number_total             2447
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            ob6093.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_sg_symbol_H-M      'P 21/c'
_cod_database_code               2200729
_cod_database_fobs_code          2200729
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -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
N1 .8869(2) .6658(2) .56096(18) .0507(6) Uani d . 1 . . N
N2 .8808(2) .6234(2) .47194(18) .0506(6) Uani d . 1 . . N
N3 1.2254(3) .9493(3) .4950(2) .0589(7) Uani d . 1 . . N
N4 .5326(2) .22395(19) .32050(17) .0468(6) Uani d . 1 . . N
O1 1.2173(3) .8883(3) .4162(2) .0989(9) Uani d . 1 . . O
O2 1.2976(3) 1.0381(3) .5199(2) .0917(8) Uani d . 1 . . O
C1 .9804(2) .7696(2) .5898(2) .0436(7) Uani d . 1 . . C
C1' .7888(3) .5217(2) .4412(2) .0417(7) Uani d . 1 . . C
C2 1.0606(3) .8100(2) .5290(2) .0479(7) Uani d . 1 . . C
H2 1.0578 .7693 .4643 .057 Uiso calc R 1 . . H
C2' .7045(3) .4750(2) .4979(2) .0455(7) Uani d . 1 . . C
H2' .7069 .5107 .5645 .055 Uiso calc R 1 . . H
C3 1.1455(2) .9119(2) .5647(2) .0399(6) Uani d . 1 . . C
C3' .6195(3) .3788(2) .45812(19) .0429(7) Uani d . 1 . . C
H3' .5635 .3487 .4977 .051 Uiso calc R 1 . . H
C4 1.1503(2) .9769(2) .65675(19) .0365(6) Uani d . 1 . . C
C4' .6129(2) .3230(2) .35933(18) .0365(6) Uani d . 1 . . C
C5' .6964(2) .3732(2) .3028(2) .0385(6) Uani d . 1 . . C
H5' .6934 .3394 .2354 .046 Uiso calc R 1 . . H
C5 1.0698(3) .9298(3) .7150(2) .0479(7) Uani d . 1 . . C
H5 1.0725 .9692 .7803 .058 Uiso calc R 1 . . H
C6' .7809(3) .4691(2) .3432(2) .0409(6) Uani d . 1 . . C
H6' .8356 .5008 .3033 .049 Uiso calc R 1 . . H
C6 .9871(3) .8298(3) .6830(2) .0516(7) Uani d . 1 . . C
H6 .9341 .8019 .7258 .062 Uiso calc R 1 . . H
C7 .4466(3) .1732(3) .3795(2) .0537(8) Uani d . 1 . . C
H7A .5012 .1472 .4505 .081 Uiso calc R 1 . . H
H7B .3980 .1013 .3411 .081 Uiso calc R 1 . . H
H7C .3831 .2369 .3864 .081 Uiso calc R 1 . . H
C8 .5184(3) .1771(3) .2148(2) .0507(7) Uani d . 1 . . C
H8A .6058 .1519 .2095 .076 Uiso calc R 1 . . H
H8B .4813 .2423 .1624 .076 Uiso calc R 1 . . H
H8C .4583 .1053 .2008 .076 Uiso calc R 1 . . H
C9 1.2335(3) 1.0900(2) .6991(2) .0517(7) Uani d . 1 . . C
H9A 1.2203 1.1148 .7670 .077 Uiso calc R 1 . . H
H9B 1.2066 1.1582 .6478 .077 Uiso calc R 1 . . H
H9C 1.3278 1.0706 .7101 .077 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
N2 N1 C1 111.6(2) no
N1 N2 C1' 112.8(2) no
O2 N3 O1 122.9(3) no
O2 N3 C3 118.5(3) no
O1 N3 C3 118.6(3) no
C4' N4 C8 120.6(2) no
C4' N4 C7 120.4(2) no
C8 N4 C7 118.5(2) no
C6 C1 C2 119.1(3) no
C6 C1 N1 116.4(2) no
C2 C1 N1 124.4(3) no
C6' C1' C2' 118.2(2) no
C6' C1' N2 115.0(2) no
C2' C1' N2 126.8(2) no
C1 C2 C3 119.1(2) no
C1 C2 H2 120.5 no
C3 C2 H2 120.5 no
C3' C2' C1' 120.7(2) no
C3' C2' H2' 119.7 no
C1' C2' H2' 119.7 no
C4 C3 C2 122.7(2) no
C4 C3 N3 121.8(2) no
C2 C3 N3 115.4(2) no
C2' C3' C4' 121.4(2) no
C2' C3' H3' 119.3 no
C4' C3' H3' 119.3 no
C3 C4 C5 115.2(2) no
C3 C4 C9 126.7(2) no
C5 C4 C9 118.1(2) no
N4 C4' C3' 122.2(2) no
N4 C4' C5' 120.9(2) no
C3' C4' C5' 116.9(2) no
C6' C5' C4' 121.2(2) no
C6' C5' H5' 119.4 no
C4' C5' H5' 119.4 no
C6 C5 C4 123.5(3) no
C6 C5 H5 118.3 no
C4 C5 H5 118.3 no
C5' C6' C1' 121.6(2) no
C5' C6' H6' 119.2 no
C1' C6' H6' 119.2 no
C5 C6 C1 120.4(3) no
C5 C6 H6 119.8 no
C1 C6 H6 119.8 no
N4 C7 H7A 109.5 no
N4 C7 H7B 109.5 no
H7A C7 H7B 109.5 no
N4 C7 H7C 109.5 no
H7A C7 H7C 109.5 no
H7B C7 H7C 109.5 no
N4 C8 H8A 109.5 no
N4 C8 H8B 109.5 no
H8A C8 H8B 109.5 no
N4 C8 H8C 109.5 no
H8A C8 H8C 109.5 no
H8B C8 H8C 109.5 no
C4 C9 H9A 109.5 no
C4 C9 H9B 109.5 no
H9A C9 H9B 109.5 no
C4 C9 H9C 109.5 no
H9A C9 H9C 109.5 no
H9B C9 H9C 109.5 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
N1 N2 . 1.239(3) yes
N1 C1 . 1.462(3) yes
N2 C1' . 1.437(3) yes
N3 O2 . 1.205(3) no
N3 O1 . 1.208(3) no
N3 C3 . 1.470(3) no
N4 C4' . 1.362(3) no
N4 C8 . 1.443(3) no
N4 C7 . 1.460(3) no
C1 C6 . 1.370(4) no
C1 C2 . 1.391(4) no
C1' C6' . 1.386(4) no
C1' C2' . 1.409(4) no
C2 C3 . 1.404(4) no
C2 H2 . .9500 no
C2' C3' . 1.367(4) no
C2' H2' . .9500 no
C3 C4 . 1.386(4) no
C3' C4' . 1.414(3) no
C3' H3' . .9500 no
C4 C5 . 1.394(4) no
C4 C9 . 1.506(4) no
C4' C5' . 1.414(3) no
C5' C6' . 1.363(3) no
C5' H5' . .9500 no
C5 C6 . 1.369(4) no
C5 H5 . .9500 no
C6' H6' . .9500 no
C6 H6 . .9500 no
C7 H7A . .9800 no
C7 H7B . .9800 no
C7 H7C . .9800 no
C8 H8A . .9800 no
C8 H8B . .9800 no
C8 H8C . .9800 no
C9 H9A . .9800 no
C9 H9B . .9800 no
C9 H9C . .9800 no
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
C1 N1 N2 C1' -179.6(2) no
N2 N1 C1 C6 175.0(2) no
N2 N1 C1 C2 -4.7(3) no
N1 N2 C1' C6' -178.5(2) no
N1 N2 C1' C2' 4.2(4) no
C6 C1 C2 C3 -.4(4) no
N1 C1 C2 C3 179.4(2) no
C6' C1' C2' C3' 1.4(4) no
N2 C1' C2' C3' 178.6(2) no
C1 C2 C3 C4 -2.1(4) no
C1 C2 C3 N3 -179.3(2) no
O2 N3 C3 C4 .8(4) no
O1 N3 C3 C4 179.6(3) no
O2 N3 C3 C2 178.1(3) no
O1 N3 C3 C2 -3.2(4) no
C1' C2' C3' C4' .0(4) no
C2 C3 C4 C5 3.4(4) no
N3 C3 C4 C5 -179.6(2) no
C2 C3 C4 C9 -177.3(2) no
N3 C3 C4 C9 -.3(4) no
C8 N4 C4' C3' 173.8(2) no
C7 N4 C4' C3' 1.5(4) no
C8 N4 C4' C5' -7.6(4) no
C7 N4 C4' C5' -179.8(2) no
C2' C3' C4' N4 177.4(2) no
C2' C3' C4' C5' -1.3(4) no
N4 C4' C5' C6' -177.4(2) no
C3' C4' C5' C6' 1.3(4) no
C3 C4 C5 C6 -2.6(4) no
C9 C4 C5 C6 178.1(3) no
C4' C5' C6' C1' .0(4) no
C2' C1' C6' C5' -1.4(4) no
N2 C1' C6' C5' -178.9(2) no
C4 C5 C6 C1 .3(4) no
C2 C1 C6 C5 1.2(4) no
N1 C1 C6 C5 -178.5(2) no
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 501951
