#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/37/2223786.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_2223786
loop_
_publ_author_name
'Tai, Xi-Shi'
'Zhao, Zeng-Bing'
_publ_section_title
;
 4-[(4-Diethylamino-2-hydroxybenzylidene)ammonio]-3-methylbenzenesulfonate
;
_journal_coeditor_code           HB5148
_journal_issue                   11
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2843
_journal_paper_doi               10.1107/S1600536809043098
_journal_volume                  65
_journal_year                    2009
_chemical_formula_iupac          'C18 H22 N2 O4 S'
_chemical_formula_moiety         'C18 H22 N2 O4 S'
_chemical_formula_sum            'C18 H22 N2 O4 S'
_chemical_formula_weight         362.44
_chemical_name_systematic
;
4-[(4-Diethylamino-2-hydroxybenzylidene)ammonio]-3-methylbenzenesulfonate
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 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                 96.848(19)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.230(9)
_cell_length_b                   12.143(14)
_cell_length_c                   18.96(2)
_cell_measurement_reflns_used    3420
_cell_measurement_temperature    273(2)
_cell_measurement_theta_max      27.78
_cell_measurement_theta_min      2.60
_cell_volume                     1881(4)
_computing_cell_refinement       'SAINT (Bruker, 2001)'
_computing_data_collection       'SMART (Bruker, 2001)'
_computing_data_reduction        'SAINT (Bruker, 2001)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      273(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker SMART CCD'
_diffrn_measurement_method       ω
_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  0.0275
_diffrn_reflns_av_sigmaI/netI    0.0328
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            9430
_diffrn_reflns_theta_full        25.05
_diffrn_reflns_theta_max         25.05
_diffrn_reflns_theta_min         2.00
_exptl_absorpt_coefficient_mu    0.196
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            brown
_exptl_crystal_density_diffrn    1.279
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             768
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.443
_refine_diff_density_min         -0.236
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     227
_refine_ls_number_reflns         3337
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.053
_refine_ls_R_factor_all          0.0563
_refine_ls_R_factor_gt           0.0459
_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)+(0.0682P)²+0.8828P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1266
_refine_ls_wR_factor_ref         0.1358
_reflns_number_gt                2737
_reflns_number_total             3337
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            hb5148.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_cell_volume        1882(4)
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               2223786
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -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
S S1 0.24693(7) 0.19093(5) 0.55953(3) 0.0423(2) Uani d . 1 . .
O O1 0.2152(3) 0.30892(16) 0.56444(12) 0.0792(7) Uani d . 1 . .
O O2 0.1087(2) 0.12620(16) 0.52607(9) 0.0582(5) Uani d . 1 . .
O O3 0.3181(2) 0.14533(16) 0.62907(8) 0.0561(5) Uani d . 1 . .
O O4 0.8678(2) 0.22390(14) 0.23964(8) 0.0496(4) Uani d . 1 . .
H H4 0.8646 0.2536 0.2006 0.074 Uiso calc R 1 . .
N N1 0.7742(2) 0.15936(16) 0.36312(9) 0.0394(4) Uani d . 1 . .
H H1 0.7599 0.2026 0.3270 0.047 Uiso calc R 1 . .
N N2 1.3356(2) 0.04143(18) 0.15486(10) 0.0513(5) Uani d . 1 . .
C C1 0.4078(3) 0.17934(17) 0.50261(11) 0.0359(5) Uani d . 1 . .
C C2 0.3808(3) 0.22288(18) 0.43351(11) 0.0396(5) Uani d . 1 . .
H H2 0.2808 0.2558 0.4183 0.047 Uiso calc R 1 . .
C C3 0.5015(3) 0.21780(18) 0.38679(11) 0.0373(5) Uani d . 1 . .
C C4 0.6527(3) 0.16570(17) 0.41184(11) 0.0349(5) Uani d . 1 . .
C C5 0.6818(3) 0.1232(2) 0.48125(11) 0.0447(6) Uani d . 1 . .
H H5 0.7821 0.0911 0.4971 0.054 Uiso calc R 1 . .
C C6 0.5588(3) 0.1295(2) 0.52658(11) 0.0437(6) Uani d . 1 . .
H H6 0.5771 0.1008 0.5723 0.052 Uiso calc R 1 . .
C C7 0.4692(3) 0.2677(2) 0.31182(13) 0.0572(7) Uani d . 1 . .
H H7A 0.3545 0.2828 0.3008 0.086 Uiso calc R 1 . .
H H7B 0.5030 0.2165 0.2778 0.086 Uiso calc R 1 . .
H H7C 0.5300 0.3349 0.3101 0.086 Uiso calc R 1 . .
C C8 0.9062(3) 0.09465(19) 0.36714(11) 0.0394(5) Uani d . 1 . .
H H8 0.9291 0.0510 0.4074 0.047 Uiso calc R 1 . .
C C9 1.0147(3) 0.08791(19) 0.31374(11) 0.0381(5) Uani d . 1 . .
C C10 0.9949(3) 0.15006(18) 0.24798(11) 0.0368(5) Uani d . 1 . .
C C11 1.0999(3) 0.13405(19) 0.19596(11) 0.0410(5) Uani d . 1 . .
H H11 1.0830 0.1739 0.1539 0.049 Uiso calc R 1 . .
C C12 1.2333(3) 0.05717(19) 0.20639(11) 0.0408(5) Uani d . 1 . .
C C13 1.2563(3) -0.0028(2) 0.27321(12) 0.0456(6) Uani d . 1 . .
H H13 1.3434 -0.0516 0.2823 0.055 Uiso calc R 1 . .
C C14 1.1492(3) 0.0123(2) 0.32326(12) 0.0452(6) Uani d . 1 . .
H H14 1.1651 -0.0285 0.3650 0.054 Uiso calc R 1 . .
C C15 1.3247(3) 0.1109(2) 0.08923(13) 0.0555(7) Uani d . 1 . .
H H15A 1.4317 0.1149 0.0728 0.067 Uiso calc R 1 . .
H H15B 1.2924 0.1850 0.1006 0.067 Uiso calc R 1 . .
C C16 1.2015(5) 0.0648(3) 0.02963(16) 0.0824(10) Uani d . 1 . .
H H16A 1.2287 -0.0102 0.0204 0.124 Uiso calc R 1 . .
H H16B 1.2051 0.1079 -0.0126 0.124 Uiso calc R 1 . .
H H16C 1.0934 0.0680 0.0438 0.124 Uiso calc R 1 . .
C C17 1.4625(3) -0.0487(2) 0.15911(15) 0.0596(7) Uani d . 1 . .
H H17A 1.4728 -0.0754 0.1116 0.072 Uiso calc R 1 . .
H H17B 1.4268 -0.1096 0.1865 0.072 Uiso calc R 1 . .
C C18 1.6273(4) -0.0090(3) 0.1931(2) 0.0841(10) Uani d . 1 . .
H H18A 1.6586 0.0554 0.1687 0.126 Uiso calc R 1 . .
H H18B 1.7073 -0.0659 0.1902 0.126 Uiso calc R 1 . .
H H18C 1.6209 0.0086 0.2420 0.126 Uiso calc R 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
O1 S1 O2 . . 114.73(14) ?
O1 S1 O3 . . 111.33(13) ?
O2 S1 O3 . . 112.88(12) ?
O1 S1 C1 . . 105.25(11) ?
O2 S1 C1 . . 106.60(12) ?
O3 S1 C1 . . 105.14(12) ?
C10 O4 H4 . . 109.5 ?
C8 N1 C4 . . 128.05(19) ?
C8 N1 H1 . . 116.0 ?
C4 N1 H1 . . 116.0 ?
C12 N2 C15 . . 122.0(2) ?
C12 N2 C17 . . 122.8(2) ?
C15 N2 C17 . . 115.20(19) ?
C2 C1 C6 . . 119.88(19) ?
C2 C1 S1 . . 118.72(17) ?
C6 C1 S1 . . 121.39(18) ?
C1 C2 C3 . . 121.6(2) ?
C1 C2 H2 . . 119.2 ?
C3 C2 H2 . . 119.2 ?
C2 C3 C4 . . 117.6(2) ?
C2 C3 C7 . . 120.4(2) ?
C4 C3 C7 . . 122.0(2) ?
C5 C4 C3 . . 121.26(19) ?
C5 C4 N1 . . 121.70(19) ?
C3 C4 N1 . . 117.04(19) ?
C6 C5 C4 . . 119.8(2) ?
C6 C5 H5 . . 120.1 ?
C4 C5 H5 . . 120.1 ?
C5 C6 C1 . . 119.9(2) ?
C5 C6 H6 . . 120.1 ?
C1 C6 H6 . . 120.1 ?
C3 C7 H7A . . 109.5 ?
C3 C7 H7B . . 109.5 ?
H7A C7 H7B . . 109.5 ?
C3 C7 H7C . . 109.5 ?
H7A C7 H7C . . 109.5 ?
H7B C7 H7C . . 109.5 ?
N1 C8 C9 . . 124.4(2) ?
N1 C8 H8 . . 117.8 ?
C9 C8 H8 . . 117.8 ?
C8 C9 C14 . . 119.0(2) ?
C8 C9 C10 . . 124.3(2) ?
C14 C9 C10 . . 116.60(19) ?
O4 C10 C11 . . 122.38(19) ?
O4 C10 C9 . . 116.42(18) ?
C11 C10 C9 . . 121.2(2) ?
C10 C11 C12 . . 121.3(2) ?
C10 C11 H11 . . 119.4 ?
C12 C11 H11 . . 119.4 ?
N2 C12 C11 . . 121.0(2) ?
N2 C12 C13 . . 121.4(2) ?
C11 C12 C13 . . 117.61(19) ?
C14 C13 C12 . . 120.3(2) ?
C14 C13 H13 . . 119.9 ?
C12 C13 H13 . . 119.9 ?
C13 C14 C9 . . 123.0(2) ?
C13 C14 H14 . . 118.5 ?
C9 C14 H14 . . 118.5 ?
N2 C15 C16 . . 112.1(2) ?
N2 C15 H15A . . 109.2 ?
C16 C15 H15A . . 109.2 ?
N2 C15 H15B . . 109.2 ?
C16 C15 H15B . . 109.2 ?
H15A C15 H15B . . 107.9 ?
C15 C16 H16A . . 109.5 ?
C15 C16 H16B . . 109.5 ?
H16A C16 H16B . . 109.5 ?
C15 C16 H16C . . 109.5 ?
H16A C16 H16C . . 109.5 ?
H16B C16 H16C . . 109.5 ?
N2 C17 C18 . . 111.9(3) ?
N2 C17 H17A . . 109.2 ?
C18 C17 H17A . . 109.2 ?
N2 C17 H17B . . 109.2 ?
C18 C17 H17B . . 109.2 ?
H17A C17 H17B . . 107.9 ?
C17 C18 H18A . . 109.5 ?
C17 C18 H18B . . 109.5 ?
H18A C18 H18B . . 109.5 ?
C17 C18 H18C . . 109.5 ?
H18A C18 H18C . . 109.5 ?
H18B C18 H18C . . 109.5 ?
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
S1 O1 . 1.461(3) ?
S1 O2 . 1.464(2) ?
S1 O3 . 1.485(2) ?
S1 C1 . 1.811(3) ?
O4 C10 . 1.372(3) ?
O4 H4 . 0.8200 ?
N1 C8 . 1.335(3) ?
N1 C4 . 1.442(3) ?
N1 H1 . 0.8600 ?
N2 C12 . 1.377(3) ?
N2 C15 . 1.497(3) ?
N2 C17 . 1.508(3) ?
C1 C2 . 1.406(3) ?
C1 C6 . 1.408(3) ?
C2 C3 . 1.409(3) ?
C2 H2 . 0.9300 ?
C3 C4 . 1.426(3) ?
C3 C7 . 1.539(3) ?
C4 C5 . 1.407(3) ?
C5 C6 . 1.406(3) ?
C5 H5 . 0.9300 ?
C6 H6 . 0.9300 ?
C7 H7A . 0.9600 ?
C7 H7B . 0.9600 ?
C7 H7C . 0.9600 ?
C8 C9 . 1.430(3) ?
C8 H8 . 0.9300 ?
C9 C14 . 1.433(3) ?
C9 C10 . 1.450(3) ?
C10 C11 . 1.401(3) ?
C11 C12 . 1.437(3) ?
C11 H11 . 0.9300 ?
C12 C13 . 1.454(3) ?
C13 C14 . 1.383(3) ?
C13 H13 . 0.9300 ?
C14 H14 . 0.9300 ?
C15 C16 . 1.531(4) ?
C15 H15A . 0.9700 ?
C15 H15B . 0.9700 ?
C16 H16A . 0.9600 ?
C16 H16B . 0.9600 ?
C16 H16C . 0.9600 ?
C17 C18 . 1.509(4) ?
C17 H17A . 0.9700 ?
C17 H17B . 0.9700 ?
C18 H18A . 0.9600 ?
C18 H18B . 0.9600 ?
C18 H18C . 0.9600 ?
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
N1 H1 O4 . 0.86 1.99 2.668(4) 135
O4 H4 O3 4_665 0.82 1.84 2.623(4) 160
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
O1 S1 C1 C2 . . . . -58.2(2) ?
O2 S1 C1 C2 . . . . 64.0(2) ?
O3 S1 C1 C2 . . . . -175.90(17) ?
O1 S1 C1 C6 . . . . 120.8(2) ?
O2 S1 C1 C6 . . . . -117.0(2) ?
O3 S1 C1 C6 . . . . 3.1(2) ?
C6 C1 C2 C3 . . . . 0.2(3) ?
S1 C1 C2 C3 . . . . 179.24(17) ?
C1 C2 C3 C4 . . . . 0.6(3) ?
C1 C2 C3 C7 . . . . -179.1(2) ?
C2 C3 C4 C5 . . . . -1.5(3) ?
C7 C3 C4 C5 . . . . 178.2(2) ?
C2 C3 C4 N1 . . . . 178.98(19) ?
C7 C3 C4 N1 . . . . -1.3(3) ?
C8 N1 C4 C5 . . . . 17.3(3) ?
C8 N1 C4 C3 . . . . -163.2(2) ?
C3 C4 C5 C6 . . . . 1.5(3) ?
N1 C4 C5 C6 . . . . -178.9(2) ?
C4 C5 C6 C1 . . . . -0.7(4) ?
C2 C1 C6 C5 . . . . -0.2(3) ?
S1 C1 C6 C5 . . . . -179.17(18) ?
C4 N1 C8 C9 . . . . 175.3(2) ?
N1 C8 C9 C14 . . . . -177.9(2) ?
N1 C8 C9 C10 . . . . -0.4(4) ?
C8 C9 C10 O4 . . . . 3.7(3) ?
C14 C9 C10 O4 . . . . -178.8(2) ?
C8 C9 C10 C11 . . . . -175.8(2) ?
C14 C9 C10 C11 . . . . 1.7(3) ?
O4 C10 C11 C12 . . . . 179.2(2) ?
C9 C10 C11 C12 . . . . -1.3(3) ?
C15 N2 C12 C11 . . . . 6.4(4) ?
C17 N2 C12 C11 . . . . -171.6(2) ?
C15 N2 C12 C13 . . . . -173.4(2) ?
C17 N2 C12 C13 . . . . 8.6(4) ?
C10 C11 C12 N2 . . . . 179.7(2) ?
C10 C11 C12 C13 . . . . -0.5(3) ?
N2 C12 C13 C14 . . . . -178.2(2) ?
C11 C12 C13 C14 . . . . 1.9(3) ?
C12 C13 C14 C9 . . . . -1.6(4) ?
C8 C9 C14 C13 . . . . 177.4(2) ?
C10 C9 C14 C13 . . . . -0.3(3) ?
C12 N2 C15 C16 . . . . -87.6(3) ?
C17 N2 C15 C16 . . . . 90.5(3) ?
C12 N2 C17 C18 . . . . -93.3(3) ?
C15 N2 C17 C18 . . . . 88.5(3) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30655918
