#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/94/2229467.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_2229467
loop_
_publ_author_name
'Gong, Liangyu'
'Lu, Lihua'
_publ_section_title
;
 4-[(2-Chloro-4-nitrophenyl)diazenyl]-N,N-diethylaniline
;
_journal_coeditor_code           NG5115
_journal_issue                   3
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o662
_journal_paper_doi               10.1107/S160053681100537X
_journal_volume                  67
_journal_year                    2011
_chemical_formula_iupac          'C16 H17 Cl N4 O2'
_chemical_formula_moiety         'C16 H17 Cl N4 O2'
_chemical_formula_sum            'C16 H17 Cl N4 O2'
_chemical_formula_weight         332.79
_chemical_name_systematic
;
4-[(2-Chloro-4-nitrophenyl)diazenyl]-N,N-diethylaniline
;
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/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                 121.795(5)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   25.745(2)
_cell_length_b                   7.5774(6)
_cell_length_c                   18.8628(15)
_cell_measurement_reflns_used    4405
_cell_measurement_temperature    110
_cell_measurement_theta_max      25.46
_cell_measurement_theta_min      2.54
_cell_volume                     3127.6(5)
_computing_cell_refinement       'SAINT (Bruker, 2006)'
_computing_data_collection       'APEX2 (Bruker, 2006)'
_computing_data_reduction        'SAINT (Bruker, 2006)'
_computing_molecular_graphics    'XP in SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SIR92 (Altomare et al., 1994)'
_diffrn_ambient_temperature      110
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker--Nonius X8 APEXII'
_diffrn_measurement_method       'φ and ω'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71070
_diffrn_reflns_av_R_equivalents  0.0620
_diffrn_reflns_av_sigmaI/netI    0.0521
_diffrn_reflns_limit_h_max       31
_diffrn_reflns_limit_h_min       -31
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            21470
_diffrn_reflns_theta_full        26.10
_diffrn_reflns_theta_max         26.10
_diffrn_reflns_theta_min         1.86
_diffrn_standards_decay_%        0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.260
_exptl_absorpt_correction_T_max  0.9897
_exptl_absorpt_correction_T_min  0.9032
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.413
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             1392
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.301
_refine_diff_density_min         -0.371
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     276
_refine_ls_number_reflns         3105
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.032
_refine_ls_R_factor_all          0.0906
_refine_ls_R_factor_gt           0.0436
_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)+(0.0616P)²+3.7461P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1037
_refine_ls_wR_factor_ref         0.1322
_reflns_number_gt                1987
_reflns_number_total             3105
_reflns_threshold_expression     I>2sigma(I)
_cod_data_source_file            ng5115.cif
_cod_data_source_block           I
_cod_original_cell_volume        3127.6(4)
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               2229467
_cod_database_fobs_code          2229467
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'
'-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
Cl Cl1 0.05101(3) 0.47275(10) 0.39144(4) 0.0324(2) Uani d . 1 . .
O O1 -0.16973(10) 0.5393(3) 0.13154(12) 0.0404(5) Uani d . 1 . .
O O2 -0.23165(9) 0.4835(3) 0.17351(13) 0.0406(6) Uani d . 1 . .
N N1 0.01886(10) 0.2751(3) 0.49659(12) 0.0221(5) Uani d . 1 . .
N N2 0.00367(10) 0.1881(3) 0.54089(13) 0.0235(5) Uani d . 1 . .
N N3 -0.18043(11) 0.4861(3) 0.18396(14) 0.0312(6) Uani d . 1 . .
C C1 -0.03294(12) 0.3220(3) 0.41830(15) 0.0230(6) Uani d . 1 . .
C C2 -0.02263(12) 0.4170(3) 0.36330(16) 0.0232(6) Uani d . 1 . .
C C3 -0.07057(13) 0.4702(4) 0.28604(16) 0.0254(6) Uani d . 1 . .
H H3 -0.0649(13) 0.545(4) 0.2500(19) 0.034(8) Uiso d . 1 . .
C C4 -0.12889(12) 0.4255(3) 0.26414(15) 0.0258(6) Uani d . 1 . .
C C5 -0.14133(13) 0.3303(4) 0.31635(16) 0.0268(6) Uani d . 1 . .
H H5 -0.1831(14) 0.302(4) 0.3003(18) 0.034(8) Uiso d . 1 . .
C C6 -0.09304(12) 0.2792(4) 0.39309(17) 0.0248(6) Uani d . 1 . .
H H6 -0.0984(13) 0.214(4) 0.4299(18) 0.035(8) Uiso d . 1 . .
C C7 0.05212(12) 0.1399(3) 0.61996(15) 0.0213(6) Uani d . 1 . .
C C8 0.11401(12) 0.1691(3) 0.65168(16) 0.0205(6) Uani d . 1 . .
H H8 0.1255(12) 0.223(4) 0.6154(16) 0.029(7) Uiso d . 1 . .
C C9 0.15720(13) 0.1204(3) 0.73204(16) 0.0220(6) Uani d . 1 . .
H H9 0.1982(14) 0.138(4) 0.7512(17) 0.035(8) Uiso d . 1 . .
C C10 0.14028(11) 0.0425(3) 0.78528(15) 0.0204(6) Uani d . 1 . .
C C11 0.07782(12) 0.0103(4) 0.75163(16) 0.0236(6) Uani d . 1 . .
H H11 0.0638(12) -0.040(3) 0.7845(17) 0.026(7) Uiso d . 1 . .
C C12 0.03514(13) 0.0575(4) 0.67093(17) 0.0241(6) Uani d . 1 . .
H H12 -0.0068(13) 0.034(3) 0.6497(17) 0.025(7) Uiso d . 1 . .
N N4 0.18316(9) -0.0024(3) 0.86547(13) 0.0233(5) Uani d . 1 . .
C C13 0.24663(12) 0.0550(4) 0.90619(17) 0.0251(6) Uani d . 1 . .
H H13A 0.2599(11) 0.074(3) 0.9655(17) 0.019(7) Uiso d . 1 . .
H H13B 0.2482(12) 0.170(4) 0.8836(16) 0.023(7) Uiso d . 1 . .
C C14 0.28708(14) -0.0772(4) 0.8975(2) 0.0293(7) Uani d . 1 . .
H H14A 0.2819(14) -0.196(5) 0.917(2) 0.053(10) Uiso d . 1 . .
H H14B 0.3270(15) -0.039(4) 0.9279(18) 0.031(8) Uiso d . 1 . .
H H14C 0.2750(13) -0.088(4) 0.8404(19) 0.030(8) Uiso d . 1 . .
C C15 0.16615(14) -0.0922(4) 0.91908(17) 0.0271(6) Uani d . 1 . .
H H15A 0.2026(13) -0.159(4) 0.9614(18) 0.034(8) Uiso d . 1 . .
H H15B 0.1330(11) -0.175(3) 0.8853(15) 0.015(6) Uiso d . 1 . .
C C16 0.14643(15) 0.0348(5) 0.96314(19) 0.0341(7) Uani d . 1 . .
H H16A 0.1835(15) 0.110(4) 1.005(2) 0.047(9) Uiso d . 1 . .
H H16B 0.1328(14) -0.027(4) 0.994(2) 0.044(9) Uiso d . 1 . .
H H16C 0.1166(13) 0.112(4) 0.9259(18) 0.029(8) 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 0.0016 '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'
Cl Cl 0.1484 0.1585 '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
N2 N1 C1 . . 111.5(2) ?
N1 N2 C7 . . 115.1(2) ?
O1 N3 O2 . . 123.7(2) ?
O1 N3 C4 . . 118.0(2) ?
O2 N3 C4 . . 118.3(2) ?
C6 C1 C2 . . 118.4(2) ?
C6 C1 N1 . . 124.2(2) ?
C2 C1 N1 . . 117.4(2) ?
C3 C2 C1 . . 121.3(3) ?
C3 C2 Cl1 . . 118.5(2) ?
C1 C2 Cl1 . . 120.2(2) ?
C4 C3 C2 . . 118.2(3) ?
C4 C3 H3 . . 119.1(18) ?
C2 C3 H3 . . 122.5(18) ?
C3 C4 C5 . . 122.6(2) ?
C3 C4 N3 . . 119.0(2) ?
C5 C4 N3 . . 118.3(2) ?
C6 C5 C4 . . 118.3(3) ?
C6 C5 H5 . . 120.2(17) ?
C4 C5 H5 . . 121.5(17) ?
C5 C6 C1 . . 121.2(3) ?
C5 C6 H6 . . 122.2(18) ?
C1 C6 H6 . . 116.6(18) ?
C8 C7 C12 . . 118.5(2) ?
C8 C7 N2 . . 126.3(2) ?
C12 C7 N2 . . 115.1(2) ?
C9 C8 C7 . . 120.5(2) ?
C9 C8 H8 . . 121.5(16) ?
C7 C8 H8 . . 118.0(16) ?
C8 C9 C10 . . 121.4(2) ?
C8 C9 H9 . . 118.9(18) ?
C10 C9 H9 . . 119.7(18) ?
N4 C10 C11 . . 121.5(2) ?
N4 C10 C9 . . 121.2(2) ?
C11 C10 C9 . . 117.3(2) ?
C12 C11 C10 . . 120.8(2) ?
C12 C11 H11 . . 118.2(17) ?
C10 C11 H11 . . 120.9(17) ?
C11 C12 C7 . . 121.4(3) ?
C11 C12 H12 . . 119.1(16) ?
C7 C12 H12 . . 119.5(16) ?
C10 N4 C13 . . 122.5(2) ?
C10 N4 C15 . . 121.3(2) ?
C13 N4 C15 . . 115.8(2) ?
N4 C13 C14 . . 112.9(2) ?
N4 C13 H13A . . 105.2(15) ?
C14 C13 H13A . . 111.6(14) ?
N4 C13 H13B . . 109.2(15) ?
C14 C13 H13B . . 110.5(15) ?
H13A C13 H13B . . 107(2) ?
C13 C14 H14A . . 108.4(18) ?
C13 C14 H14B . . 109.2(18) ?
H14A C14 H14B . . 112(3) ?
C13 C14 H14C . . 110.1(17) ?
H14A C14 H14C . . 109(2) ?
H14B C14 H14C . . 109(2) ?
N4 C15 C16 . . 113.0(3) ?
N4 C15 H15A . . 107.0(16) ?
C16 C15 H15A . . 109.2(16) ?
N4 C15 H15B . . 108.9(14) ?
C16 C15 H15B . . 109.6(14) ?
H15A C15 H15B . . 109(2) ?
C15 C16 H16A . . 108.9(18) ?
C15 C16 H16B . . 111.3(19) ?
H16A C16 H16B . . 107(3) ?
C15 C16 H16C . . 111.5(17) ?
H16A C16 H16C . . 107(3) ?
H16B C16 H16C . . 110(3) ?
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
Cl1 C2 . 1.731(3) ?
O1 N3 . 1.226(3) ?
O2 N3 . 1.226(3) ?
N1 N2 . 1.276(3) ?
N1 C1 . 1.418(3) ?
N2 C7 . 1.398(3) ?
N3 C4 . 1.464(3) ?
C1 C6 . 1.397(4) ?
C1 C2 . 1.398(4) ?
C2 C3 . 1.384(4) ?
C3 C4 . 1.373(4) ?
C3 H3 . 0.95(3) ?
C4 C5 . 1.388(4) ?
C5 C6 . 1.376(4) ?
C5 H5 . 0.98(3) ?
C6 H6 . 0.92(3) ?
C7 C8 . 1.393(4) ?
C7 C12 . 1.396(4) ?
C8 C9 . 1.376(4) ?
C8 H8 . 0.97(3) ?
C9 C10 . 1.417(4) ?
C9 H9 . 0.93(3) ?
C10 N4 . 1.365(3) ?
C10 C11 . 1.405(4) ?
C11 C12 . 1.375(4) ?
C11 H11 . 0.95(3) ?
C12 H12 . 0.95(3) ?
N4 C13 . 1.458(3) ?
N4 C15 . 1.465(3) ?
C13 C14 . 1.514(4) ?
C13 H13A . 0.99(3) ?
C13 H13B . 0.98(3) ?
C14 H14A . 1.01(3) ?
C14 H14B . 0.92(3) ?
C14 H14C . 0.96(3) ?
C15 C16 . 1.523(4) ?
C15 H15A . 0.99(3) ?
C15 H15B . 0.98(3) ?
C16 H16A . 1.03(3) ?
C16 H16B . 0.95(3) ?
C16 H16C . 0.93(3) ?
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
C1 N1 N2 C7 . . . . -178.7(2) ?
N2 N1 C1 C6 . . . . 0.3(4) ?
N2 N1 C1 C2 . . . . -179.6(2) ?
C6 C1 C2 C3 . . . . 0.9(4) ?
N1 C1 C2 C3 . . . . -179.1(2) ?
C6 C1 C2 Cl1 . . . . -179.81(19) ?
N1 C1 C2 Cl1 . . . . 0.1(3) ?
C1 C2 C3 C4 . . . . -0.7(4) ?
Cl1 C2 C3 C4 . . . . 180.0(2) ?
C2 C3 C4 C5 . . . . 0.2(4) ?
C2 C3 C4 N3 . . . . 177.8(2) ?
O1 N3 C4 C3 . . . . 16.2(4) ?
O2 N3 C4 C3 . . . . -162.6(2) ?
O1 N3 C4 C5 . . . . -166.1(2) ?
O2 N3 C4 C5 . . . . 15.0(4) ?
C3 C4 C5 C6 . . . . 0.0(4) ?
N3 C4 C5 C6 . . . . -177.5(2) ?
C4 C5 C6 C1 . . . . 0.2(4) ?
C2 C1 C6 C5 . . . . -0.7(4) ?
N1 C1 C6 C5 . . . . 179.4(2) ?
N1 N2 C7 C8 . . . . -3.9(4) ?
N1 N2 C7 C12 . . . . 175.0(2) ?
C12 C7 C8 C9 . . . . -1.2(4) ?
N2 C7 C8 C9 . . . . 177.7(2) ?
C7 C8 C9 C10 . . . . -1.1(4) ?
C8 C9 C10 N4 . . . . -178.7(2) ?
C8 C9 C10 C11 . . . . 2.6(4) ?
N4 C10 C11 C12 . . . . 179.5(2) ?
C9 C10 C11 C12 . . . . -1.8(4) ?
C10 C11 C12 C7 . . . . -0.5(4) ?
C8 C7 C12 C11 . . . . 2.0(4) ?
N2 C7 C12 C11 . . . . -177.0(2) ?
C11 C10 N4 C13 . . . . -169.7(2) ?
C9 C10 N4 C13 . . . . 11.6(4) ?
C11 C10 N4 C15 . . . . 2.3(4) ?
C9 C10 N4 C15 . . . . -176.4(2) ?
C10 N4 C13 C14 . . . . -92.7(3) ?
C15 N4 C13 C14 . . . . 94.9(3) ?
C10 N4 C15 C16 . . . . -85.4(3) ?
C13 N4 C15 C16 . . . . 87.1(3) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 2282681
