#------------------------------------------------------------------------------
#$Date: 2011-09-10 04:16:28 +0100 (Sat, 10 Sep 2011) $
#$Revision: 25271 $
#$URL: svn://www.crystallography.net/cod/cif/2/2006652.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_2006652
loop_
_publ_author_name
'Zhang, D.-C.'
'Fei, Z.-H.'
'Zhang, T.-Z.'
'Zhang, Y.-Q.'
'Yu, K.-B.'
_publ_contact_author
;
 Assoc.Prof.De-Chun Zhang
 Department of Chemistry
 Suzhou University
 Suzhou 215006
 People's Republic of China
;
_publ_section_title
;
 2-Nitro-4'-(<i>N</i>,<i>N</i>-diethylamino)azobenzene,
 C~16~H~18~N~4~O~2~
;
_journal_issue                   11
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              1647
_journal_page_last               1648
_journal_volume                  53
_journal_year                    1997
_chemical_formula_structural     C6H4NO2NNC6H4N(C2H5)2
_chemical_formula_sum            'C16 H18 N4 O2'
_chemical_formula_weight         298.34
_chemical_melting_point          .378E-305
_chemical_name_systematic
;
 ?
;
_space_group_IT_number           60
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2n 2ab'
_symmetry_space_group_name_H-M   'P b c n'
_audit_creation_method           SHELXL
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   17.366(3)
_cell_length_b                   8.196(2)
_cell_length_c                   20.999(4)
_cell_measurement_reflns_used    32
_cell_measurement_temperature    291(2)
_cell_measurement_theta_max      15.48
_cell_measurement_theta_min      2.35
_cell_volume                     2988.8(11)
_computing_cell_refinement       XSCANS
_computing_data_collection       'XSCANS (Siemens, 1994)'
_computing_data_reduction        'SHELXTL (Sheldrick, 1994)'
_computing_molecular_graphics    SHELXTL
_computing_publication_material  SHELXTL
_computing_structure_refinement  'SHELXL93 (Sheldrick, 1993)'
_computing_structure_solution    'SHELXS86 (Sheldrick, 1990)'
_diffrn_ambient_temperature      291(2)
_diffrn_measurement_device       'Siemens P4'
_diffrn_measurement_method       '\w scans'
_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  0.0107
_diffrn_reflns_av_sigmaI/netI    0.0447
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       1
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            2188
_diffrn_reflns_theta_max         24.00
_diffrn_reflns_theta_min         1.94
_diffrn_standards_decay_%        1.40
_diffrn_standards_interval_count 97
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.091
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            Red
_exptl_crystal_density_diffrn    1.326
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_description       'Hexagonal prism'
_exptl_crystal_F_000             1264
_exptl_crystal_size_max          0.54
_exptl_crystal_size_mid          0.54
_exptl_crystal_size_min          0.46
_refine_diff_density_max         0.134
_refine_diff_density_min         -0.113
_refine_ls_extinction_coef       0.0047(4)
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_all   0.875
_refine_ls_goodness_of_fit_obs   1.078
_refine_ls_hydrogen_treatment    'H atoms refined isotropically'
_refine_ls_matrix_type           full
_refine_ls_number_parameters     272
_refine_ls_number_reflns         2080
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.875
_refine_ls_restrained_S_obs      1.078
_refine_ls_R_factor_all          0.0631
_refine_ls_R_factor_obs          0.0334
_refine_ls_shift/esd_max         0.003
_refine_ls_shift/esd_mean        0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_scheme
'calc w = 1/[\s^2^(Fo^2^)+(0.0374P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_wR_factor_all         0.0751
_refine_ls_wR_factor_obs         0.0694
_reflns_number_observed          1288
_reflns_number_total             2080
_reflns_observed_criterion       >2sigma(I)
_[local]_cod_data_source_file    bs1041.cif
_[local]_cod_data_source_block   y474
_cod_database_code               2006652
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y+1/2, z+1/2'
'-x, y, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y-1/2, -z-1/2'
'x, -y, z-1/2'
'-x-1/2, y-1/2, z'
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_12
_atom_site_aniso_U_13
_atom_site_aniso_U_23
O1 0.0927(15) 0.0465(12) 0.0764(13) -0.0132(11) 0.0131(11) -0.0204(10)
O2 0.0688(12) 0.0682(13) 0.0522(11) -0.0088(10) 0.0129(9) 0.0035(9)
N1 0.0444(12) 0.047(2) 0.0488(13) 0.0004(11) -0.0023(10) -0.0050(11)
N2 0.0456(12) 0.0456(13) 0.0438(11) 0.0074(10) 0.0010(9) -0.0063(10)
N3 0.0408(11) 0.0430(13) 0.0414(11) -0.0015(10) 0.0014(9) -0.0067(9)
N4 0.0500(12) 0.0401(13) 0.0424(11) 0.0112(10) 0.0013(9) -0.0007(10)
C1 0.0398(13) 0.035(2) 0.0370(12) 0.0022(12) -0.0052(11) -0.0047(11)
C2 0.0421(15) 0.045(2) 0.0401(14) 0.0066(13) 0.0006(12) -0.0008(13)
C3 0.057(2) 0.043(2) 0.048(2) 0.0155(15) -0.0023(13) -0.0076(13)
C4 0.059(2) 0.040(2) 0.0499(15) 0.0004(15) -0.0014(13) 0.0009(13)
C5 0.049(2) 0.048(2) 0.0407(14) 0.0032(14) 0.0014(12) -0.0022(13)
C6 0.0391(13) 0.040(2) 0.0352(12) 0.0074(12) -0.0053(11) -0.0050(11)
C7 0.0368(12) 0.0302(14) 0.0416(14) 0.0003(11) 0.0007(11) -0.0061(11)
C8 0.0415(14) 0.039(2) 0.0409(14) 0.0019(12) -0.0028(11) -0.0007(12)
C9 0.0457(14) 0.0406(15) 0.0340(13) 0.0008(12) 0.0021(11) -0.0027(12)
C10 0.0345(12) 0.0315(14) 0.0427(13) -0.0017(11) -0.0024(10) -0.0013(11)
C11 0.0511(15) 0.038(2) 0.0390(13) 0.0047(13) -0.0017(12) 0.0015(12)
C12 0.0494(14) 0.042(2) 0.0351(13) -0.0026(12) 0.0024(11) -0.0039(12)
C13 0.047(2) 0.035(2) 0.0478(15) 0.0013(13) 0.0022(12) -0.0087(12)
C14 0.063(2) 0.073(3) 0.055(2) -0.016(2) 0.009(2) -0.008(2)
C15 0.047(2) 0.050(2) 0.056(2) 0.0096(14) 0.0038(14) -0.0012(14)
C16 0.071(2) 0.051(2) 0.083(2) 0.003(2) 0.020(2) 0.006(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_thermal_displace_type
_atom_site_calc_flag
_atom_site_occupancy
_atom_site_type_symbol
O1 0.14512(11) 0.2480(2) 0.77972(9) 0.0718(6) Uani d 1 O
O2 0.18483(9) 0.1372(2) 0.69308(8) 0.0631(5) Uani d 1 O
N1 0.15280(10) 0.1300(3) 0.74511(9) 0.0468(5) Uani d 1 N
N2 0.02542(10) 0.1017(2) 0.83292(8) 0.0450(5) Uani d 1 N
N3 0.01142(10) 0.0995(2) 0.89220(8) 0.0417(5) Uani d 1 N
N4 -0.16169(10) 0.6094(2) 0.99597(8) 0.0441(5) Uani d 1 N
C1 0.12420(12) -0.0287(3) 0.76636(9) 0.0372(6) Uani d 1 C
C2 0.15914(14) -0.1649(3) 0.74143(11) 0.0426(6) Uani d 1 C
C3 0.13673(14) -0.3174(4) 0.76144(11) 0.0491(7) Uani d 1 C
C4 0.07897(15) -0.3322(3) 0.80658(11) 0.0497(7) Uani d 1 C
C5 0.04417(14) -0.1953(3) 0.83114(11) 0.0456(6) Uani d 1 C
C6 0.06596(12) -0.0394(3) 0.81224(9) 0.0381(6) Uani d 1 C
C7 -0.03219(12) 0.2328(2) 0.91454(9) 0.0362(6) Uani d 1 C
C8 -0.04541(13) 0.2377(3) 0.97953(10) 0.0406(6) Uani d 1 C
C9 -0.08743(13) 0.3617(3) 1.00651(11) 0.0401(6) Uani d 1 C
C10 -0.11888(12) 0.4876(3) 0.96965(10) 0.0362(5) Uani d 1 C
C11 -0.10452(14) 0.4796(3) 0.90359(10) 0.0427(6) Uani d 1 C
C12 -0.06237(13) 0.3569(3) 0.87702(11) 0.0423(6) Uani d 1 C
C13 -0.16515(14) 0.6346(3) 1.06465(11) 0.0433(6) Uani d 1 C
C14 -0.2336(2) 0.5544(4) 1.09579(15) 0.0638(8) Uani d 1 C
C15 -0.20296(15) 0.7297(3) 0.95741(13) 0.0512(7) Uani d 1 C
C16 -0.1553(2) 0.8789(4) 0.9433(2) 0.0683(9) Uani d 1 C
H2 0.2002(11) -0.150(2) 0.7101(9) 0.040(6) Uiso d 1 H
H3 0.1636(12) -0.412(3) 0.7462(9) 0.047(7) Uiso d 1 H
H4 0.0615(12) -0.441(3) 0.8224(9) 0.053(7) Uiso d 1 H
H5 0.0059(13) -0.202(3) 0.8660(11) 0.066(8) Uiso d 1 H
H8 -0.0224(11) 0.155(2) 1.0064(9) 0.038(6) Uiso d 1 H
H9 -0.0951(10) 0.361(2) 1.0517(9) 0.038(6) Uiso d 1 H
H11 -0.1233(12) 0.564(3) 0.8793(9) 0.046(7) Uiso d 1 H
H12 -0.0556(11) 0.355(2) 0.8331(9) 0.036(5) Uiso d 1 H
H13A -0.1671(11) 0.755(3) 1.0697(8) 0.036(6) Uiso d 1 H
H13B -0.1142(13) 0.596(2) 1.0837(9) 0.051(7) Uiso d 1 H
H14A -0.2282(15) 0.429(4) 1.0903(11) 0.088(10) Uiso d 1 H
H14B -0.2324(13) 0.583(3) 1.1389(11) 0.069(8) Uiso d 1 H
H14C -0.2824(17) 0.585(3) 1.0738(12) 0.098(11) Uiso d 1 H
H15A -0.2209(11) 0.680(3) 0.9159(9) 0.050(7) Uiso d 1 H
H15B -0.2510(13) 0.763(3) 0.9824(9) 0.061(7) Uiso d 1 H
H16A -0.1083(16) 0.850(3) 0.9196(12) 0.086(9) Uiso d 1 H
H16B -0.1384(15) 0.933(3) 0.9854(13) 0.098(11) Uiso d 1 H
H16C -0.188(2) 0.958(4) 0.9190(15) 0.145(15) Uiso d 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 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
_geom_angle_publ_flag
O1 N1 O2 122.9(2) ?
O1 N1 C1 119.2(2) yes
O2 N1 C1 117.9(2) yes
N3 N2 C6 112.5(2) yes
N2 N3 C7 114.8(2) yes
C10 N4 C13 121.9(2) yes
C10 N4 C15 122.5(2) yes
C13 N4 C15 115.6(2) ?
C2 C1 C6 122.0(2) ?
C2 C1 N1 117.2(2) yes
C6 C1 N1 120.8(2) yes
C1 C2 C3 119.8(2) ?
C2 C3 C4 119.6(2) ?
C5 C4 C3 120.2(3) ?
C4 C5 C6 121.5(2) ?
C5 C6 C1 116.8(2) ?
C5 C6 N2 121.7(2) yes
C1 C6 N2 121.1(2) yes
C8 C7 C12 118.4(2) ?
C8 C7 N3 116.1(2) yes
C12 C7 N3 125.5(2) yes
C9 C8 C7 121.1(2) ?
C8 C9 C10 121.6(2) ?
N4 C10 C9 121.9(2) yes
N4 C10 C11 122.0(2) yes
C9 C10 C11 116.1(2) ?
C12 C11 C10 122.1(2) ?
C11 C12 C7 120.7(2) ?
N4 C13 C14 113.6(2) yes
N4 C15 C16 112.7(2) yes
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
O1 N1 1.217(2) yes
O2 N1 1.227(2) yes
N1 C1 1.462(3) yes
N2 N3 1.268(2) yes
N2 C6 1.422(2) yes
N3 C7 1.410(2) yes
N4 C10 1.362(2) yes
N4 C13 1.458(3) yes
N4 C15 1.463(3) yes
C1 C2 1.374(3) ?
C1 C6 1.399(3) ?
C2 C3 1.375(3) ?
C3 C4 1.385(3) ?
C4 C5 1.375(3) ?
C5 C6 1.390(3) ?
C7 C8 1.384(3) ?
C7 C12 1.389(3) ?
C8 C9 1.373(3) ?
C9 C10 1.401(3) ?
C10 C11 1.411(3) ?
C11 C12 1.363(3) ?
C13 C14 1.508(3) ?
C15 C16 1.506(4) ?
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
C6 N2 N3 C7 -176.9(2) yes
O1 N1 C1 C2 -154.1(2) ?
O2 N1 C1 C2 24.7(3) ?
O1 N1 C1 C6 23.2(3) ?
O2 N1 C1 C6 -157.9(2) ?
C6 C1 C2 C3 0.3(3) ?
N1 C1 C2 C3 177.5(2) ?
C1 C2 C3 C4 0.1(3) ?
C2 C3 C4 C5 0.1(4) ?
C3 C4 C5 C6 -0.6(3) ?
C4 C5 C6 C1 0.9(3) ?
C4 C5 C6 N2 174.0(2) ?
C2 C1 C6 C5 -0.7(3) ?
N1 C1 C6 C5 -177.9(2) ?
C2 C1 C6 N2 -173.9(2) ?
N1 C1 C6 N2 9.0(3) ?
N3 N2 C6 C5 45.9(3) ?
N3 N2 C6 C1 -141.3(2) ?
N2 N3 C7 C8 -177.2(2) ?
N2 N3 C7 C12 3.0(3) ?
C12 C7 C8 C9 0.1(3) ?
N3 C7 C8 C9 -179.8(2) ?
C7 C8 C9 C10 0.3(3) ?
C13 N4 C10 C9 12.1(3) ?
C15 N4 C10 C9 -172.0(2) ?
C13 N4 C10 C11 -168.8(2) ?
C15 N4 C10 C11 7.1(3) ?
C8 C9 C10 N4 178.9(2) ?
C8 C9 C10 C11 -0.3(3) ?
N4 C10 C11 C12 -179.3(2) ?
C9 C10 C11 C12 -0.1(3) ?
C10 C11 C12 C7 0.6(3) ?
C8 C7 C12 C11 -0.6(3) ?
N3 C7 C12 C11 179.3(2) ?
C10 N4 C13 C14 -95.6(3) ?
C15 N4 C13 C14 88.3(3) ?
C10 N4 C15 C16 -90.6(3) ?
C13 N4 C15 C16 85.5(3) ?