#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/88/2228869.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_2228869
loop_
_publ_author_name
'Gervasio, Giuliana'
'Marabello, Domenica'
'Bertolotti, Federica'
_publ_section_title
;
 4-({4-[Bis(2-cyanoethyl)amino]phenyl}diazenyl)benzenesulfonamide
;
_journal_coeditor_code           RZ2541
_journal_issue                   1
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o231
_journal_paper_doi               10.1107/S1600536810053158
_journal_volume                  67
_journal_year                    2011
_chemical_formula_iupac          'C18 H18 N6 O2 S'
_chemical_formula_moiety         'C18 H18 N6 O2 S'
_chemical_formula_sum            'C18 H18 N6 O2 S'
_chemical_formula_weight         382.45
_chemical_name_systematic
;
4-({4-[Bis(2-cyanoethyl)amino]phenyl}diazenyl)benzenesulfonamide
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                94.268(4)
_cell_angle_beta                 106.544(4)
_cell_angle_gamma                104.568(5)
_cell_formula_units_Z            2
_cell_length_a                   7.8093(16)
_cell_length_b                   11.035(2)
_cell_length_c                   11.776(3)
_cell_measurement_reflns_used    52
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      20.2
_cell_measurement_theta_min      1.9
_cell_volume                     929.8(3)
_computing_cell_refinement       'SAINT (Bruker, 2007)'
_computing_data_collection       'SMART (Bruker, 2007)'
_computing_data_reduction        'SAINT (Bruker, 2007)'
_computing_molecular_graphics    'XP (Sheldrick, 2008)'
_computing_publication_material  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      295(2)
_diffrn_measured_fraction_theta_full 0.879
_diffrn_measured_fraction_theta_max 0.879
_diffrn_measurement_device_type  'Siemens--Bruker APEX'
_diffrn_measurement_method       φ
_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  0.0401
_diffrn_reflns_av_sigmaI/netI    0.1796
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            9271
_diffrn_reflns_theta_full        28.37
_diffrn_reflns_theta_max         28.37
_diffrn_reflns_theta_min         1.83
_diffrn_standards_decay_%        0
_diffrn_standards_interval_time  60
_diffrn_standards_number         15
_exptl_absorpt_coefficient_mu    0.200
_exptl_absorpt_correction_T_max  1.00
_exptl_absorpt_correction_T_min  0.93
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SORTAV; Blessing, 1995)'
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.359
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             400
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.404
_refine_diff_density_min         -0.480
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.858
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     244
_refine_ls_number_reflns         4100
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.858
_refine_ls_R_factor_all          0.1188
_refine_ls_R_factor_gt           0.0495
_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)] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0552
_refine_ls_wR_factor_ref         0.0552
_reflns_number_gt                1577
_reflns_number_total             4100
_reflns_threshold_expression     I>2sigma(I)
_cod_data_source_file            rz2541.cif
_cod_data_source_block           I
_cod_database_code               2228869
_cod_database_fobs_code          2228869
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
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 -0.4369(3) 0.3324(2) 0.1462(2) 0.0329(7) Uani d . 1 . .
C C2 -0.3729(3) 0.2269(2) 0.1422(2) 0.0385(7) Uani d . 1 . .
H H2A -0.4475 0.1532 0.0896 0.046 Uiso calc R 1 . .
C C3 -0.1985(3) 0.2304(2) 0.2160(2) 0.0397(7) Uani d . 1 . .
H H3A -0.1535 0.1603 0.2117 0.048 Uiso calc R 1 . .
C C4 -0.0912(3) 0.3396(2) 0.2967(2) 0.0338(7) Uani d . 1 . .
C C5 -0.1585(3) 0.4427(2) 0.3021(2) 0.0474(8) Uani d . 1 . .
H H5A -0.0880 0.5146 0.3582 0.057 Uiso calc R 1 . .
C C6 -0.3308(3) 0.4404(2) 0.2245(2) 0.0438(8) Uani d . 1 . .
H H6A -0.3735 0.5118 0.2258 0.053 Uiso calc R 1 . .
S S7 -0.66133(10) 0.32583(7) 0.05031(7) 0.0441(2) Uani d . 1 . .
O O8 -0.6950(2) 0.44536(15) 0.07477(14) 0.0586(6) Uani d . 1 . .
O O9 -0.6729(2) 0.27865(16) -0.06983(13) 0.0548(6) Uani d . 1 . .
N N10 -0.8133(3) 0.2210(2) 0.0862(2) 0.0468(7) Uani d . 1 . .
H H10A -0.817(3) 0.243(2) 0.1638(18) 0.056 Uiso d . 1 . .
H H10B -0.799(3) 0.1427(19) 0.0698(19) 0.056 Uiso d . 1 . .
N N11 0.0845(3) 0.34976(19) 0.38119(16) 0.0416(6) Uani d . 1 . .
N N12 0.1748(3) 0.28313(18) 0.34648(16) 0.0402(6) Uani d . 1 . .
C C13 0.3437(3) 0.2869(2) 0.4342(2) 0.0343(7) Uani d . 1 . .
C C14 0.4404(3) 0.2039(2) 0.4088(2) 0.0406(8) Uani d . 1 . .
H H14A 0.3980 0.1541 0.3336 0.049 Uiso calc R 1 . .
C C15 0.5974(3) 0.1942(2) 0.4928(2) 0.0416(8) Uani d . 1 . .
H H15A 0.6601 0.1382 0.4737 0.050 Uiso calc R 1 . .
C C16 0.6644(3) 0.2679(2) 0.6072(2) 0.0373(7) Uani d . 1 . .
C C17 0.5725(3) 0.3570(2) 0.6288(2) 0.0388(7) Uani d . 1 . .
H H17A 0.6186 0.4110 0.7019 0.047 Uiso calc R 1 . .
C C18 0.4168(3) 0.3660(2) 0.5447(2) 0.0365(7) Uani d . 1 . .
H H18A 0.3586 0.4259 0.5614 0.044 Uiso calc R 1 . .
N N19 0.8150(3) 0.2551(2) 0.69548(18) 0.0471(7) Uani d . 1 . .
C C20 0.9028(4) 0.1477(3) 0.6819(2) 0.0713(10) Uani d . 1 . .
H H20A 0.9460 0.1199 0.7584 0.086 Uiso calc R 1 . .
H H20B 0.8126 0.0760 0.6252 0.086 Uiso calc R 1 . .
C C21 1.0583(4) 0.1988(3) 0.6383(2) 0.0766(10) Uani d . 1 . .
H H21A 1.1448 0.2737 0.6924 0.092 Uiso calc R 1 . .
H H21B 1.0145 0.2216 0.5594 0.092 Uiso calc R 1 . .
C C22 1.1544(4) 0.0919(3) 0.6327(3) 0.0738(11) Uani d . 1 . .
N N23 1.2304(4) 0.0229(2) 0.6272(2) 0.0917(10) Uani d . 1 . .
C C24 0.8777(3) 0.3258(2) 0.8154(2) 0.0445(8) Uani d . 1 . .
H H24A 0.8795 0.4133 0.8098 0.053 Uiso calc R 1 . .
H H24B 1.0046 0.3248 0.8548 0.053 Uiso calc R 1 . .
C C25 0.7577(3) 0.2751(2) 0.8932(2) 0.0538(8) Uani d . 1 . .
H H25A 0.8088 0.3273 0.9717 0.065 Uiso calc R 1 . .
H H25B 0.6327 0.2814 0.8571 0.065 Uiso calc R 1 . .
C C26 0.7480(4) 0.1423(3) 0.9075(3) 0.0547(9) Uani d . 1 . .
N N27 0.7442(3) 0.0422(2) 0.9183(2) 0.0735(9) Uani 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'
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'
S S 0.1246 0.1234 '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
C6 C1 C2 . . 120.7(2) ?
C6 C1 S7 . . 119.93(19) ?
C2 C1 S7 . . 119.4(2) ?
C1 C2 C3 . . 120.2(2) ?
C1 C2 H2A . . 119.9 ?
C3 C2 H2A . . 119.9 ?
C2 C3 C4 . . 119.3(2) ?
C2 C3 H3A . . 120.4 ?
C4 C3 H3A . . 120.4 ?
C5 C4 C3 . . 120.0(2) ?
C5 C4 N11 . . 116.5(2) ?
C3 C4 N11 . . 123.5(2) ?
C4 C5 C6 . . 120.5(2) ?
C4 C5 H5A . . 119.7 ?
C6 C5 H5A . . 119.7 ?
C1 C6 C5 . . 119.3(2) ?
C1 C6 H6A . . 120.3 ?
C5 C6 H6A . . 120.3 ?
O8 S7 O9 . . 119.73(10) ?
O8 S7 N10 . . 106.68(11) ?
O9 S7 N10 . . 106.08(12) ?
O8 S7 C1 . . 108.04(11) ?
O9 S7 C1 . . 107.70(11) ?
N10 S7 C1 . . 108.15(12) ?
S7 N10 H10A . . 112.7(14) ?
S7 N10 H10B . . 109.6(15) ?
H10A N10 H10B . . 116(2) ?
N12 N11 C4 . . 114.1(2) ?
N11 N12 C13 . . 113.8(2) ?
C14 C13 C18 . . 118.2(2) ?
C14 C13 N12 . . 117.5(2) ?
C18 C13 N12 . . 124.3(2) ?
C15 C14 C13 . . 121.2(2) ?
C15 C14 H14A . . 119.4 ?
C13 C14 H14A . . 119.4 ?
C14 C15 C16 . . 120.6(2) ?
C14 C15 H15A . . 119.7 ?
C16 C15 H15A . . 119.7 ?
N19 C16 C17 . . 120.6(2) ?
N19 C16 C15 . . 121.9(2) ?
C17 C16 C15 . . 117.5(2) ?
C18 C17 C16 . . 121.3(2) ?
C18 C17 H17A . . 119.4 ?
C16 C17 H17A . . 119.4 ?
C17 C18 C13 . . 121.0(2) ?
C17 C18 H18A . . 119.5 ?
C13 C18 H18A . . 119.5 ?
C16 N19 C24 . . 122.0(2) ?
C16 N19 C20 . . 122.3(2) ?
C24 N19 C20 . . 114.63(19) ?
C21 C20 N19 . . 106.4(3) ?
C21 C20 H20A . . 110.4 ?
N19 C20 H20A . . 110.4 ?
C21 C20 H20B . . 110.4 ?
N19 C20 H20B . . 110.4 ?
H20A C20 H20B . . 108.6 ?
C20 C21 C22 . . 106.0(3) ?
C20 C21 H21A . . 110.5 ?
C22 C21 H21A . . 110.5 ?
C20 C21 H21B . . 110.5 ?
C22 C21 H21B . . 110.5 ?
H21A C21 H21B . . 108.7 ?
N23 C22 C21 . . 175.3(4) ?
N19 C24 C25 . . 114.2(2) ?
N19 C24 H24A . . 108.7 ?
C25 C24 H24A . . 108.7 ?
N19 C24 H24B . . 108.7 ?
C25 C24 H24B . . 108.7 ?
H24A C24 H24B . . 107.6 ?
C26 C25 C24 . . 112.5(2) ?
C26 C25 H25A . . 109.1 ?
C24 C25 H25A . . 109.1 ?
C26 C25 H25B . . 109.1 ?
C24 C25 H25B . . 109.1 ?
H25A C25 H25B . . 107.8 ?
N27 C26 C25 . . 178.6(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
C1 C6 . 1.364(3) ?
C1 C2 . 1.381(3) ?
C1 S7 . 1.775(2) ?
C2 C3 . 1.381(3) ?
C2 H2A . 0.9300 ?
C3 C4 . 1.387(3) ?
C3 H3A . 0.9300 ?
C4 C5 . 1.373(3) ?
C4 N11 . 1.419(3) ?
C5 C6 . 1.388(3) ?
C5 H5A . 0.9300 ?
C6 H6A . 0.9300 ?
S7 O8 . 1.4326(15) ?
S7 O9 . 1.4403(15) ?
S7 N10 . 1.610(2) ?
N10 H10A . 0.939(19) ?
N10 H10B . 0.913(19) ?
N11 N12 . 1.259(2) ?
N12 C13 . 1.414(3) ?
C13 C14 . 1.390(3) ?
C13 C18 . 1.393(3) ?
C14 C15 . 1.372(3) ?
C14 H14A . 0.9300 ?
C15 C16 . 1.405(3) ?
C15 H15A . 0.9300 ?
C16 N19 . 1.376(3) ?
C16 C17 . 1.403(3) ?
C17 C18 . 1.363(3) ?
C17 H17A . 0.9300 ?
C18 H18A . 0.9300 ?
N19 C24 . 1.447(3) ?
N19 C20 . 1.530(3) ?
C20 C21 . 1.452(3) ?
C20 H20A . 0.9700 ?
C20 H20B . 0.9700 ?
C21 C22 . 1.556(3) ?
C21 H21A . 0.9700 ?
C21 H21B . 0.9700 ?
C22 N23 . 1.085(3) ?
C24 C25 . 1.527(3) ?
C24 H24A . 0.9700 ?
C24 H24B . 0.9700 ?
C25 C26 . 1.472(3) ?
C25 H25A . 0.9700 ?
C25 H25B . 0.9700 ?
C26 N27 . 1.116(3) ?
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
_geom_hbond_publ_flag
C15 H15A N23 2_756 0.93 2.52 3.427(4) 166 yes
N10 H10B N27 2_556 0.91(2) 2.19(2) 3.084(2) 165 yes
N10 H10A N12 1_455 0.94(2) 2.19(2) 3.124(2) 176 yes
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30656438
