#------------------------------------------------------------------------------
#$Date: 2023-03-09 11:15:39 +0200 (Thu, 09 Mar 2023) $
#$Revision: 281763 $
#$URL: file:///home/coder/svn-repositories/cod/cif/8/10/68/8106890.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_8106890
loop_
_publ_author_name
'Oh, In-Hwan'
'Park, Seong-Hun'
_publ_section_title
;
 Crystal structure of
 (E)-4-(2-(4-(diethylamino)phenyl)diazen-1-ium-1-yl)benzenesulfonate
 monohydrate
;
_journal_issue                   2
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              409
_journal_page_last               410
_journal_paper_doi               10.1515/ncrs-2015-0042
_journal_volume                  231
_journal_year                    2016
_chemical_formula_moiety         'C16 h19 N3 O3 S, H2 O'
_chemical_formula_sum            'C16 H21 N3 O4 S'
_chemical_formula_weight         351.42
_chemical_name_systematic
;
(E)-4-(2-(4-(diethylamino)phenyl)diazen-1-ium-1-yl)benzenesulfonate monohydrate
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   difmap
_cell_angle_alpha                102.382(4)
_cell_angle_beta                 109.303(4)
_cell_angle_gamma                97.122(4)
_cell_formula_units_Z            2
_cell_length_a                   8.402(2)
_cell_length_b                   9.035(2)
_cell_length_c                   11.692(3)
_cell_measurement_reflns_used    2516
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      28.28
_cell_measurement_theta_min      2.36
_cell_volume                     799.7(3)
_computing_cell_refinement       'Bruker SAINT [9]'
_computing_data_collection       'Bruker SMART [10]'
_computing_data_reduction        'Bruker SAINT [9]'
_computing_molecular_graphics
;
Diamond Version 3.2.e [13]
;
_computing_publication_material  'PublCIF [14]'
_computing_structure_refinement  'SHELXL-2014 [8]'
_computing_structure_solution    'WINGX SIR92 [12]'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.983
_diffrn_measured_fraction_theta_max 0.904
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0180
_diffrn_reflns_av_unetI/netI     0.0395
_diffrn_reflns_Laue_measured_fraction_full 0.983
_diffrn_reflns_Laue_measured_fraction_max 0.904
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_number            4982
_diffrn_reflns_point_group_measured_fraction_full 0.983
_diffrn_reflns_point_group_measured_fraction_max 0.904
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         28.290
_diffrn_reflns_theta_min         1.918
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.230
_exptl_absorpt_correction_T_max  0.9954
_exptl_absorpt_correction_T_min  0.9097
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Bruker SADABS [11]'
_exptl_crystal_colour            dark-red
_exptl_crystal_density_diffrn    1.459
_exptl_crystal_description       plate
_exptl_crystal_F_000             372
_exptl_crystal_size_max          0.420
_exptl_crystal_size_mid          0.400
_exptl_crystal_size_min          0.020
_refine_diff_density_max         0.345
_refine_diff_density_min         -0.366
_refine_diff_density_rms         0.060
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_hydrogen_treatment    refxyz
_refine_ls_matrix_type           full
_refine_ls_number_parameters     282
_refine_ls_number_reflns         3593
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.052
_refine_ls_R_factor_all          0.0552
_refine_ls_R_factor_gt           0.0410
_refine_ls_shift/su_max          0.006
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0614P)²+0.2458P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1078
_refine_ls_wR_factor_ref         0.1172
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2835
_reflns_number_total             3593
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            suppl_ncrs-2015-0042_suppl.cif
_cod_data_source_block           oO3_25tr
_cod_database_code               8106890
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_min   0.910
_shelx_estimated_absorpt_t_max   0.995
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 1.42225(5) 0.48840(5) 0.72009(4) 0.02011(14) Uani 1 1 d . . . . .
O1 O 1.45566(16) 0.65011(15) 0.78826(13) 0.0266(3) Uani 1 1 d . . . . .
O2 O 1.47156(17) 0.46816(17) 0.61014(13) 0.0301(3) Uani 1 1 d . . . . .
O3 O 1.48984(18) 0.38923(16) 0.79832(14) 0.0315(3) Uani 1 1 d . . . . .
O1S O 0.3209(2) 0.6983(2) 0.98325(17) 0.0484(5) Uani 1 1 d . . . . .
H1O H 0.376(4) 0.674(4) 0.919(3) 0.073 Uiso 1 1 d . U . . .
H2O H 0.382(4) 0.653(4) 1.045(3) 0.073 Uiso 1 1 d . U . . .
N1 N 0.6598(2) 0.26440(18) 0.48802(15) 0.0227(3) Uani 1 1 d . . . . .
H1N H 0.598(3) 0.338(3) 0.495(2) 0.034 Uiso 1 1 d . U . . .
N2 N 0.59461(19) 0.11974(18) 0.42646(15) 0.0221(3) Uani 1 1 d . . . . .
N3 N -0.0842(2) -0.12834(19) 0.11924(16) 0.0249(4) Uani 1 1 d . . . . .
C1 C 1.1949(2) 0.4217(2) 0.65877(17) 0.0197(4) Uani 1 1 d . . . . .
C2 C 1.1262(2) 0.2657(2) 0.59324(18) 0.0237(4) Uani 1 1 d . . . . .
H2 H 1.200(3) 0.194(3) 0.582(2) 0.028 Uiso 1 1 d . U . . .
C3 C 0.9494(2) 0.2109(2) 0.53783(19) 0.0245(4) Uani 1 1 d . . . . .
H3 H 0.903(3) 0.107(3) 0.493(2) 0.029 Uiso 1 1 d . U . . .
C4 C 0.8399(2) 0.3130(2) 0.54899(17) 0.0208(4) Uani 1 1 d . . . . .
C5 C 0.9070(2) 0.4668(2) 0.61799(19) 0.0239(4) Uani 1 1 d . . . . .
H5 H 0.829(3) 0.536(3) 0.628(2) 0.029 Uiso 1 1 d . U . . .
C6 C 1.0852(2) 0.5213(2) 0.67236(18) 0.0231(4) Uani 1 1 d . . . . .
H6 H 1.131(3) 0.628(3) 0.722(2) 0.028 Uiso 1 1 d . U . . .
C7 C 0.4253(2) 0.0714(2) 0.35882(17) 0.0204(4) Uani 1 1 d . . . . .
C8 C 0.3719(2) -0.0907(2) 0.29769(18) 0.0228(4) Uani 1 1 d . . . . .
H8 H 0.457(3) -0.148(3) 0.310(2) 0.027 Uiso 1 1 d . U . . .
C9 C 0.2059(2) -0.1570(2) 0.22234(18) 0.0227(4) Uani 1 1 d . . . . .
H9 H 0.179(3) -0.263(3) 0.183(2) 0.030(6) Uiso 1 1 d . . . . .
C10 C 0.0782(2) -0.0650(2) 0.19825(18) 0.0222(4) Uani 1 1 d . . . . .
C11 C 0.1314(2) 0.0979(2) 0.2616(2) 0.0271(4) Uani 1 1 d . . . . .
H11 H 0.048(3) 0.164(3) 0.248(2) 0.033 Uiso 1 1 d . U . . .
C12 C 0.2978(2) 0.1635(2) 0.3391(2) 0.0257(4) Uani 1 1 d . . . . .
H12 H 0.327(3) 0.274(3) 0.380(2) 0.031 Uiso 1 1 d . U . . .
C13 C -0.1463(2) -0.2979(2) 0.0655(2) 0.0253(4) Uani 1 1 d . . . . .
H13A H -0.267(3) -0.322(3) 0.050(2) 0.030 Uiso 1 1 d . U . . .
H13B H -0.091(3) -0.350(3) 0.131(2) 0.030 Uiso 1 1 d . U . . .
C14 C -0.1180(3) -0.3543(3) -0.0565(2) 0.0305(5) Uani 1 1 d . . . . .
H14A H -0.178(3) -0.298(3) -0.118(2) 0.037 Uiso 1 1 d . U . . .
H14B H -0.163(3) -0.466(3) -0.091(2) 0.037 Uiso 1 1 d . U . . .
H14C H 0.000(3) -0.333(2) -0.042(2) 0.026(5) Uiso 1 1 d . . . . .
C15 C -0.2141(3) -0.0344(3) 0.0782(2) 0.0296(4) Uani 1 1 d . . . . .
H15A H -0.292(3) -0.093(3) -0.008(2) 0.036 Uiso 1 1 d . U . . .
H15B H -0.157(3) 0.065(3) 0.071(2) 0.036 Uiso 1 1 d . U . . .
C16 C -0.3090(3) -0.0042(3) 0.1680(3) 0.0374(5) Uani 1 1 d . . . . .
H16A H -0.356(3) -0.101(3) 0.170(2) 0.045 Uiso 1 1 d . U . . .
H16B H -0.397(3) 0.062(3) 0.135(2) 0.045 Uiso 1 1 d . U . . .
H16C H -0.227(3) 0.062(3) 0.253(3) 0.045 Uiso 1 1 d . U . . .
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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
O3 S1 O1 114.21(9) . .
O3 S1 O2 112.63(9) . .
O1 S1 O2 112.24(8) . .
O3 S1 C1 105.30(9) . .
O1 S1 C1 106.33(8) . .
O2 S1 C1 105.23(8) . .
H1O O1S H2O 101(3) . .
N2 N1 C4 118.95(16) . .
N2 N1 H1N 124.9(15) . .
C4 N1 H1N 116.2(15) . .
N1 N2 C7 120.72(16) . .
C10 N3 C13 122.05(16) . .
C10 N3 C15 122.73(16) . .
C13 N3 C15 115.22(15) . .
C6 C1 C2 119.77(16) . .
C6 C1 S1 121.59(14) . .
C2 C1 S1 118.63(14) . .
C3 C2 C1 120.48(17) . .
C3 C2 H2 118.0(13) . .
C1 C2 H2 121.5(13) . .
C2 C3 C4 119.33(17) . .
C2 C3 H3 120.9(14) . .
C4 C3 H3 119.8(14) . .
C5 C4 C3 120.55(16) . .
C5 C4 N1 118.21(16) . .
C3 C4 N1 121.22(16) . .
C4 C5 C6 119.68(17) . .
C4 C5 H5 119.7(13) . .
C6 C5 H5 120.6(13) . .
C1 C6 C5 120.13(17) . .
C1 C6 H6 120.7(13) . .
C5 C6 H6 119.2(13) . .
N2 C7 C8 114.50(16) . .
N2 C7 C12 127.48(17) . .
C8 C7 C12 117.99(16) . .
C9 C8 C7 121.78(17) . .
C9 C8 H8 121.6(13) . .
C7 C8 H8 116.6(13) . .
C8 C9 C10 120.72(17) . .
C8 C9 H9 117.9(14) . .
C10 C9 H9 121.3(14) . .
N3 C10 C9 121.12(17) . .
N3 C10 C11 121.41(17) . .
C9 C10 C11 117.46(16) . .
C12 C11 C10 121.52(18) . .
C12 C11 H11 118.5(13) . .
C10 C11 H11 120.0(13) . .
C11 C12 C7 120.46(18) . .
C11 C12 H12 118.5(14) . .
C7 C12 H12 121.1(14) . .
N3 C13 C14 111.75(16) . .
N3 C13 H13A 107.8(13) . .
C14 C13 H13A 109.4(13) . .
N3 C13 H13B 108.8(13) . .
C14 C13 H13B 113.4(13) . .
H13A C13 H13B 105.4(18) . .
C13 C14 H14A 109.0(13) . .
C13 C14 H14B 110.0(14) . .
H14A C14 H14B 110.4(19) . .
C13 C14 H14C 110.2(13) . .
H14A C14 H14C 108.5(19) . .
H14B C14 H14C 108.6(19) . .
N3 C15 C16 111.10(19) . .
N3 C15 H15A 105.9(14) . .
C16 C15 H15A 112.5(14) . .
N3 C15 H15B 110.1(14) . .
C16 C15 H15B 110.9(13) . .
H15A C15 H15B 106.0(19) . .
C15 C16 H16A 105.5(16) . .
C15 C16 H16B 107.5(14) . .
H16A C16 H16B 115(2) . .
C15 C16 H16C 110.2(15) . .
H16A C16 H16C 113(2) . .
H16B C16 H16C 105(2) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 O3 1.4479(15) . y
S1 O1 1.4491(14) . y
S1 O2 1.4586(14) . y
S1 C1 1.7749(18) . y
O1S H1O 1.00(3) . ?
O1S H2O 0.94(3) . ?
N1 N2 1.298(2) . ?
N1 C4 1.407(2) . ?
N1 H1N 0.90(2) . ?
N2 C7 1.340(2) . ?
N3 C10 1.338(2) . ?
N3 C13 1.479(2) . ?
N3 C15 1.483(3) . ?
C1 C6 1.388(3) . ?
C1 C2 1.396(3) . ?
C2 C3 1.384(3) . ?
C2 H2 0.97(2) . ?
C3 C4 1.398(3) . ?
C3 H3 0.94(2) . ?
C4 C5 1.387(3) . ?
C5 C6 1.393(3) . ?
C5 H5 0.98(2) . ?
C6 H6 0.97(2) . ?
C7 C8 1.426(3) . ?
C7 C12 1.426(3) . ?
C8 C9 1.354(3) . ?
C8 H8 0.93(2) . ?
C9 C10 1.429(3) . ?
C9 H9 0.93(2) . ?
C10 C11 1.437(3) . ?
C11 C12 1.362(3) . ?
C11 H11 0.97(2) . ?
C12 H12 0.97(2) . ?
C13 C14 1.516(3) . ?
C13 H13A 0.96(2) . ?
C13 H13B 1.00(2) . ?
C14 H14A 1.00(3) . ?
C14 H14B 0.98(2) . ?
C14 H14C 0.94(2) . ?
C15 C16 1.515(3) . ?
C15 H15A 0.99(2) . ?
C15 H15B 1.00(2) . ?
C16 H16A 0.93(3) . ?
C16 H16B 1.04(3) . ?
C16 H16C 1.01(3) . ?
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_site_symmetry_A
_geom_hbond_publ_flag
N1 H1N O2 0.90(2) 2.37(2) 3.064(2) 134.0(19) 2_766 y
N1 H1N O2 0.90(2) 2.22(2) 3.003(2) 146(2) 1_455 y
O1S H1O O1 1.00(3) 1.85(3) 2.841(2) 170(3) 1_455 y
O1S H2O O3 0.94(3) 1.94(4) 2.858(2) 165(3) 2_767 y
