A solid-state oxidation of 1,1,3,3-tetramethylguanidinium 4-methylbenzenesulfinate to 1,1,3,3-tetramethylguanidinium 4-methylbenzenesulfonate
Kaupang, Åsmund; Görbitz, Carl Henrik; Bonge-Hansen, Tore; Acta Crystallographica Section C 69 (2013) 778–780; doi:10.1107/S0108270113015011

data_2019027
_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 S-'
_chemical_formula_moiety         'C5 H14 N3 +, C7 H7 O2 S -'
_chemical_formula_sum            'C12 H21 N3 O2 S'
_chemical_formula_weight         271.38
_chemical_name_common
'1,1,3,3-tetramethylguanidine <i>p</i>-toluenesulfinate'
_chemical_name_systematic
;
1,1,3,3-Tetramethylguanidinium 4-methylbenzenesulfinate
;
_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                 92.1150(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   11.0959(8)
_cell_length_b                   7.4038(5)
_cell_length_c                   17.1944(13)
_cell_measurement_reflns_used    7132
_cell_measurement_temperature    105(2)
_cell_measurement_theta_max      28.2155
_cell_measurement_theta_min      2.2225
_cell_volume                     1411.59(18)
_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      105(2)
_diffrn_detector_area_resol_mean 8.3
_diffrn_measured_fraction_theta_full 0.981
_diffrn_measured_fraction_theta_max 0.966
_diffrn_measurement_device_type  'Bruker APEXII CCD area-detector'
_diffrn_measurement_method
'Sets of exposures each taken over 0.5\% \w 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  0.0167
_diffrn_reflns_av_sigmaI/netI    0.0152
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            11987
_diffrn_reflns_theta_full        27.96
_diffrn_reflns_theta_max         28.25
_diffrn_reflns_theta_min         1.84
_diffrn_standards_decay_%        0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.229
_exptl_absorpt_correction_T_max  0.9336
_exptl_absorpt_correction_T_min  0.8572
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2007)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.277
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             584
_exptl_crystal_size_max          0.6
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.3
_refine_diff_density_max         0.447
_refine_diff_density_min         -0.250
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     174
_refine_ls_number_reflns         3375
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.047
_refine_ls_R_factor_all          0.0345
_refine_ls_R_factor_gt           0.0302
_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/[\s^2^(Fo^2^)+(0.0440P)^2^+0.5937P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0812
_refine_ls_wR_factor_ref         0.0851
_reflns_number_gt                3026
_reflns_number_total             3375
_reflns_threshold_expression     I>2\s(I)
_cod_data_source_file            eg3125.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2019027
_cod_database_fobs_code          2019027