#------------------------------------------------------------------------------
#$Date: 2016-02-20 00:18:51 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176760 $
#$URL: svn://www.crystallography.net/cod/cif/2/01/90/2019028.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_2019028
loop_
_publ_author_name
'Kaupang, Åsmund'
'Görbitz, Carl Henrik'
'Bonge-Hansen, Tore'
_publ_section_title
;
 A solid-state oxidation of 1,1,3,3-tetramethylguanidinium
 4-methylbenzenesulfinate to 1,1,3,3-tetramethylguanidinium
 4-methylbenzenesulfonate
;
_journal_coeditor_code           EG3125
_journal_issue                   7
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              778
_journal_page_last               780
_journal_paper_doi               10.1107/S0108270113015011
_journal_volume                  69
_journal_year                    2013
_chemical_formula_iupac          'C5 H14 N3 + , C7 H7 O2.82 S -'
_chemical_formula_moiety         'C5 H14 N3 +, C7 H7 O2.82 S -'
_chemical_formula_sum            'C12 H21 N3 O2.82 S'
_chemical_formula_weight         284.44
_chemical_name_common
'1,1,3,3-tetramethylguanidine p-toluenesulfonate'
_chemical_name_systematic
;
1,1,3,3-Tetramethylguanidinium 4-methylbenzenesulfonate
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL97
_cell_angle_alpha                90.00
_cell_angle_beta                 93.169(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   11.185(3)
_cell_length_b                   7.648(2)
_cell_length_c                   17.415(5)
_cell_measurement_reflns_used    2504
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      24.7030
_cell_measurement_theta_min      2.3425
_cell_volume                     1487.5(7)
_computing_cell_refinement       'SAINT-Plus (Bruker, 2007)'
_computing_data_collection       'APEX2 (Bruker, 2007)'
_computing_data_reduction        'SAINT-Plus (Bruker, 2007)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXTL (Sheldrick, 2008)'
_computing_structure_solution    'SHELXTL (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_detector_area_resol_mean 8.3
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker APEXII CCD area-detector'
_diffrn_measurement_method
'Sets of exposures each taken over 0.5° ω rotation'
_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  0.0450
_diffrn_reflns_av_sigmaI/netI    0.0424
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            10043
_diffrn_reflns_theta_full        25.04
_diffrn_reflns_theta_max         25.04
_diffrn_reflns_theta_min         1.82
_diffrn_standards_decay_%        0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.226
_exptl_absorpt_correction_T_max  0.9558
_exptl_absorpt_correction_T_min  0.7103
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2007)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.270
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             610.1
_exptl_crystal_size_max          0.8
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.329
_refine_diff_density_min         -0.376
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.081
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     187
_refine_ls_number_reflns         2615
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.081
_refine_ls_R_factor_all          0.1195
_refine_ls_R_factor_gt           0.0628
_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)+(0.0241P)²+2.8813P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1305
_refine_ls_wR_factor_ref         0.1546
_reflns_number_gt                1587
_reflns_number_total             2615
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            eg3125.cif
_cod_data_source_block           II
_cod_original_cell_volume        1487.5(8)
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2019028
_cod_database_fobs_code          2019028
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -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_symmetry_multiplicity
S S1 0.29495(10) 0.56175(19) 0.40703(8) 0.0653(4) Uani d . 1 1
O O1 0.3460(4) 0.4551(9) 0.3592(3) 0.142(3) Uani d P 0.816(12) 1
O O2 0.3510(3) 0.7310(5) 0.4107(3) 0.1321(19) Uani d . 1 1
O O3 0.2812(3) 0.4933(4) 0.48344(18) 0.0768(10) Uani d . 1 1
N N1 0.4054(3) 0.1976(6) 0.5527(2) 0.0648(11) Uani d . 1 1
H H11 0.370(4) 0.274(6) 0.531(3) 0.078 Uiso d . 1 1
H H12 0.483(4) 0.215(6) 0.571(2) 0.078 Uiso d . 1 1
N N2 0.3989(3) -0.0456(5) 0.62949(19) 0.0543(9) Uani d . 1 1
N N3 0.2466(3) 0.0096(5) 0.5376(2) 0.0606(10) Uani d . 1 1
C C9 -0.0649(4) 0.5739(6) 0.3758(2) 0.0580(12) Uani d . 1 1
H H91 -0.1295 0.5335 0.4022 0.070 Uiso calc R 1 1
C C11 0.0499(3) 0.5440(6) 0.4053(2) 0.0536(11) Uani d . 1 1
H H111 0.0618 0.4820 0.4511 0.064 Uiso calc R 1 1
C C1 0.3513(3) 0.0534(6) 0.5729(2) 0.0500(10) Uani d . 1 1
C C12 0.1465(3) 0.6038(5) 0.3686(2) 0.0464(10) Uani d . 1 1
C C7 -0.0852(4) 0.6621(6) 0.3081(2) 0.0546(11) Uani d . 1 1
C C10 0.1274(4) 0.6953(6) 0.3016(3) 0.0661(13) Uani d . 1 1
H H101 0.1920 0.7386 0.2762 0.079 Uiso calc R 1 1
C C5 0.4852(4) 0.0232(8) 0.6870(3) 0.0744(15) Uani d . 1 1
H H51 0.4738 -0.0319 0.7356 0.11(2) Uiso calc R 1 1
H H52 0.4742 0.1471 0.6918 0.091(18) Uiso calc R 1 1
H H53 0.5648 -0.0001 0.6718 0.12(2) Uiso calc R 1 1
C C3 0.2110(5) 0.0756(7) 0.4608(3) 0.0843(17) Uani d . 1 1
H H31 0.1704 -0.0151 0.4315 0.126 Uiso calc R 1 1
H H32 0.2808 0.1113 0.4353 0.126 Uiso calc R 1 1
H H33 0.1583 0.1737 0.4652 0.126 Uiso calc R 1 1
C C6 -0.2104(4) 0.6907(8) 0.2732(3) 0.0868(17) Uani d . 1 1
H H61 -0.2260 0.8139 0.2691 0.130 Uiso calc R 1 1
H H62 -0.2673 0.6377 0.3054 0.130 Uiso calc R 1 1
H H63 -0.2174 0.6387 0.2230 0.130 Uiso calc R 1 1
C C2 0.1546(4) -0.0843(7) 0.5762(3) 0.0931(18) Uani d . 1 1
H H21 0.1468 -0.2001 0.5553 0.140 Uiso calc R 1 1
H H22 0.0797 -0.0237 0.5685 0.140 Uiso calc R 1 1
H H23 0.1762 -0.0911 0.6302 0.140 Uiso calc R 1 1
C C8 0.0122(4) 0.7232(7) 0.2719(3) 0.0698(14) Uani d . 1 1
H H81 0.0003 0.7851 0.2261 0.084 Uiso calc R 1 1
C C4 0.3906(4) -0.2361(6) 0.6268(3) 0.0763(15) Uani d . 1 1
H H41 0.3509 -0.2713 0.5790 0.114 Uiso calc R 1 1
H H42 0.3458 -0.2767 0.6687 0.114 Uiso calc R 1 1
H H43 0.4696 -0.2854 0.6309 0.114 Uiso calc R 1 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
O1 S1 O2 . . 112.5(4)
O1 S1 O3 . 1 115.4(3)
O2 S1 O3 . 1 110.7(3)
O1 S1 C12 . . 107.5(3)
O2 S1 C12 . . 104.4(2)
O3 S1 C12 1 . 105.42(19)
O3 S1 C12 . . 105.42(19)
C1 N1 H11 . . 122(4)
C1 N1 H12 . . 118(3)
H11 N1 H12 . . 120(5)
C1 N2 C5 . . 121.9(4)
C1 N2 C4 . . 121.5(4)
C5 N2 C4 . . 115.0(4)
C1 N3 C2 . . 122.6(4)
C1 N3 C3 . . 121.4(4)
C2 N3 C3 . . 115.4(4)
C7 C9 C11 . . 120.8(4)
C7 C9 H91 . . 119.6
C11 C9 H91 . . 119.6
C12 C11 C9 . . 121.0(4)
C12 C11 H111 . . 119.5
C9 C11 H111 . . 119.5
N1 C1 N2 . . 120.3(4)
N1 C1 N3 . . 119.5(4)
N2 C1 N3 . . 120.2(4)
C11 C12 C10 . . 118.8(4)
C11 C12 S1 . . 120.5(3)
C10 C12 S1 . . 120.7(3)
C9 C7 C8 . . 117.8(4)
C9 C7 C6 . . 121.7(4)
C8 C7 C6 . . 120.5(4)
C12 C10 C8 . . 120.0(4)
C12 C10 H101 . . 120.0
C8 C10 H101 . . 120.0
N2 C5 H51 . . 109.5
N2 C5 H52 . . 109.5
H51 C5 H52 . . 109.5
N2 C5 H53 . . 109.5
H51 C5 H53 . . 109.5
H52 C5 H53 . . 109.5
N3 C3 H31 . . 109.5
N3 C3 H32 . . 109.5
H31 C3 H32 . . 109.5
N3 C3 H33 . . 109.5
H31 C3 H33 . . 109.5
H32 C3 H33 . . 109.5
C7 C6 H61 . . 109.5
C7 C6 H62 . . 109.5
H61 C6 H62 . . 109.5
C7 C6 H63 . . 109.5
H61 C6 H63 . . 109.5
H62 C6 H63 . . 109.5
N3 C2 H21 . . 109.5
N3 C2 H22 . . 109.5
H21 C2 H22 . . 109.5
N3 C2 H23 . . 109.5
H21 C2 H23 . . 109.5
H22 C2 H23 . . 109.5
C7 C8 C10 . . 121.6(4)
C7 C8 H81 . . 119.2
C10 C8 H81 . . 119.2
N2 C4 H41 . . 109.5
N2 C4 H42 . . 109.5
H41 C4 H42 . . 109.5
N2 C4 H43 . . 109.5
H41 C4 H43 . . 109.5
H42 C4 H43 . . 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
S1 O1 . 1.318(5)
S1 O2 . 1.438(4)
S1 O3 1 1.446(3)
S1 O3 . 1.446(3)
S1 C12 . 1.785(4)
N1 C1 . 1.315(5)
N1 H11 . 0.79(5)
N1 H12 . 0.92(5)
N2 C1 . 1.330(5)
N2 C5 . 1.452(5)
N2 C4 . 1.460(6)
N3 C1 . 1.335(5)
N3 C2 . 1.450(6)
N3 C3 . 1.464(5)
C9 C7 . 1.365(6)
C9 C11 . 1.376(5)
C9 H91 . 0.9300
C11 C12 . 1.365(5)
C11 H111 . 0.9300
C12 C10 . 1.367(5)
C7 C8 . 1.372(6)
C7 C6 . 1.511(6)
C10 C8 . 1.378(6)
C10 H101 . 0.9300
C5 H51 . 0.9600
C5 H52 . 0.9600
C5 H53 . 0.9600
C3 H31 . 0.9600
C3 H32 . 0.9600
C3 H33 . 0.9600
C6 H61 . 0.9600
C6 H62 . 0.9600
C6 H63 . 0.9600
C2 H21 . 0.9600
C2 H22 . 0.9600
C2 H23 . 0.9600
C8 H81 . 0.9300
C4 H41 . 0.9600
C4 H42 . 0.9600
C4 H43 . 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 H12 O2 3_666 0.92(5) 1.91(5) 2.817(5) 169(4)
N1 H11 O3 1 0.79(5) 2.10(5) 2.884(5) 174(5)
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
C7 C9 C11 C12 . 1.0(7)
C5 N2 C1 N1 . 20.9(6)
C4 N2 C1 N1 . -143.7(5)
C5 N2 C1 N3 . -157.2(4)
C4 N2 C1 N3 . 38.1(6)
C2 N3 C1 N1 . -148.1(5)
C3 N3 C1 N1 . 22.9(7)
C2 N3 C1 N2 . 30.0(6)
C3 N3 C1 N2 . -158.9(4)
C9 C11 C12 C10 . 0.2(7)
C9 C11 C12 S1 . -179.2(3)
O1 S1 C12 C11 . 112.7(5)
O2 S1 C12 C11 . -127.6(4)
O3 S1 C12 C11 1 -10.9(4)
O3 S1 C12 C11 . -10.9(4)
O1 S1 C12 C10 . -66.7(5)
O2 S1 C12 C10 . 52.9(4)
O3 S1 C12 C10 1 169.6(4)
O3 S1 C12 C10 . 169.6(4)
C11 C9 C7 C8 . -1.6(7)
C11 C9 C7 C6 . 177.8(4)
C11 C12 C10 C8 . -0.9(7)
S1 C12 C10 C8 . 178.5(4)
C9 C7 C8 C10 . 0.9(7)
C6 C7 C8 C10 . -178.5(5)
C12 C10 C8 C7 . 0.4(8)
