#------------------------------------------------------------------------------
#$Date: 2017-10-13 03:48:21 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201957 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/01/20/2012020.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_2012020
loop_
_publ_author_name
'Steiner, Thomas'
_publ_section_title
;
 The C---H···O hydrogen bond in
 (dicyanomethyl)ammonium p-toluenesulfonate
;
_journal_issue                   6
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              775
_journal_page_last               776
_journal_paper_doi               10.1107/S0108270101005789
_journal_volume                  57
_journal_year                    2001
_chemical_formula_moiety         'C3 H4 N3 + , C7 H7 O3 S - '
_chemical_formula_sum            'C10 H11 N3 O3 S'
_chemical_formula_weight         253.28
_chemical_name_common            'aminomalononitrile p-toluenesulfonate'
_chemical_name_systematic
;
 Ammonio-malononitrile p-toluenesulfonate
;
_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'
_cell_angle_alpha                90.00
_cell_angle_beta                 96.40(14)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   5.604(9)
_cell_length_b                   25.90(5)
_cell_length_c                   8.427(12)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      14.9
_cell_measurement_theta_min      8.2
_cell_volume                     1216(4)
_computing_cell_refinement       'STOE Diffractometer Software'
_computing_data_collection
'STOE Diffractometer Software (Stoe & Cie, 1993)'
_computing_data_reduction        'STOE Diffractometer Software'
_computing_molecular_graphics    'PLATON (Spek, 1990)'
_computing_publication_material  SHELXL97
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS86 (Sheldrick, 1986)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full .998
_diffrn_measured_fraction_theta_max .998
_diffrn_measurement_device_type  'STOE for-circle diffractometer'
_diffrn_measurement_method       ω-scans
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     .71073
_diffrn_reflns_av_R_equivalents  .0185
_diffrn_reflns_av_sigmaI/netI    .0283
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       33
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            3001
_diffrn_reflns_theta_full        27.03
_diffrn_reflns_theta_max         27.03
_diffrn_reflns_theta_min         2.56
_diffrn_standards_decay_%        3
_diffrn_standards_interval_time  90
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    .267
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.384
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             528
_exptl_crystal_size_max          .8
_exptl_crystal_size_mid          .3
_exptl_crystal_size_min          .05
_refine_diff_density_max         .447
_refine_diff_density_min         -.389
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     171
_refine_ls_number_reflns         2660
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.025
_refine_ls_R_factor_all          .0604
_refine_ls_R_factor_gt           .0451
_refine_ls_shift/su_max          <0.001
_refine_ls_shift/su_mean         .000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0656P)²+0.4531P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         .1260
_reflns_number_gt                2162
_reflns_number_total             2660
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            de1169.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21 /n'
_cod_database_code               2012020
_cod_database_fobs_code          2012020
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_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
_atom_site_type_symbol
S1 .74752(8) .190589(19) .62961(5) .03177(16) Uani d . 1 . . S
O1 .7303(3) .22032(6) .77468(16) .0393(4) Uani d . 1 . . O
O2 .5660(3) .20656(6) .50249(17) .0416(4) Uani d . 1 . . O
O3 .9874(3) .19285(6) .58114(19) .0421(4) Uani d . 1 . . O
C1 .6888(4) .12601(8) .6734(2) .0376(4) Uani d . 1 . . C
C2 .4753(5) .10355(10) .6150(3) .0555(6) Uani d . 1 . . C
H2 .3612 .1220 .5491 .067 Uiso calc R 1 . . H
C3 .4331(6) .05303(12) .6559(4) .0701(8) Uani d . 1 . . C
H3 .2887 .0377 .6162 .084 Uiso calc R 1 . . H
C4 .5962(6) .02478(11) .7530(4) .0649(8) Uani d . 1 . . C
C5 .8057(6) .04836(12) .8096(4) .0749(9) Uani d . 1 . . C
H5 .9188 .0300 .8764 .090 Uiso calc R 1 . . H
C6 .8552(5) .09854(11) .7707(3) .0585(7) Uani d . 1 . . C
H6 1.0002 .1137 .8102 .070 Uiso calc R 1 . . H
C7 .5440(8) -.03045(12) .7971(5) .1013(14) Uani d . 1 . . C
H7A .4951 -.0314 .9027 .152 Uiso calc R 1 . . H
H7B .6861 -.0510 .7942 .152 Uiso calc R 1 . . H
H7C .4177 -.0440 .7224 .152 Uiso calc R 1 . . H
N1 .7754(3) .23564(8) 1.2375(2) .0358(4) Uani d . 1 . . N
H1A .705(5) .2282(10) 1.326(3) .043(6) Uiso d . 1 . . H
H1B .694(5) .2636(11) 1.186(3) .048(7) Uiso d . 1 . . H
H1C .932(5) .2464(10) 1.261(3) .057(8) Uiso d . 1 . . H
N2 .3287(4) .17136(10) 1.0170(3) .0660(6) Uani d . 1 . . N
N3 .9688(5) .11085(11) 1.2746(4) .0798(8) Uani d . 1 . . N
C8 .7701(4) .19072(9) 1.1300(2) .0379(5) Uani d . 1 . . C
H8 .856(4) .2001(9) 1.043(3) .040(6) Uiso d . 1 . . H
C9 .5202(4) .17894(10) 1.0673(3) .0460(5) Uani d . 1 . . C
C10 .8828(4) .14550(10) 1.2127(3) .0496(6) Uani d . 1 . . C
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C .0033 .0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H .0000 .0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N .0061 .0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O .0106 .0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S .1246 .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_publ_flag
O3 S1 O2 112.08(14) ?
O3 S1 O1 111.42(14) ?
O2 S1 O1 111.22(14) ?
O3 S1 C1 107.45(10) ?
O2 S1 C1 107.14(11) ?
O1 S1 C1 107.24(14) ?
C6 C1 C2 120.2(3) ?
C6 C1 S1 119.4(2) ?
C2 C1 S1 120.40(19) ?
C1 C2 C3 118.6(3) ?
C1 C2 H2 120.7 ?
C3 C2 H2 120.7 ?
C4 C3 C2 122.3(3) ?
C4 C3 H3 118.8 ?
C2 C3 H3 118.8 ?
C5 C4 C3 117.5(3) ?
C5 C4 C7 121.4(3) ?
C3 C4 C7 121.2(3) ?
C4 C5 C6 122.0(3) ?
C4 C5 H5 119.0 ?
C6 C5 H5 119.0 ?
C1 C6 C5 119.4(3) ?
C1 C6 H6 120.3 ?
C5 C6 H6 120.3 ?
C4 C7 H7A 109.5 ?
C4 C7 H7B 109.5 ?
H7A C7 H7B 109.5 ?
C4 C7 H7C 109.5 ?
H7A C7 H7C 109.5 ?
H7B C7 H7C 109.5 ?
C8 N1 H1A 111.0(16) ?
C8 N1 H1B 110.5(16) ?
H1A N1 H1B 108(2) ?
C8 N1 H1C 108.9(17) ?
H1A N1 H1C 112(2) ?
H1B N1 H1C 105(2) ?
C10 C8 C9 110.3(2) y
C10 C8 N1 111.1(2) y
C9 C8 N1 109.7(2) y
C10 C8 H8 109.8(14) ?
C9 C8 H8 108.7(15) ?
N1 C8 H8 107.1(14) ?
N2 C9 C8 177.8(3) ?
N3 C10 C8 179.5(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
S1 O3 . 1.449(3) ?
S1 O2 . 1.453(3) ?
S1 O1 . 1.457(2) ?
S1 C1 . 1.752(4) ?
C1 C6 . 1.370(4) ?
C1 C2 . 1.372(4) ?
C2 C3 . 1.380(5) ?
C2 H2 . .9300 ?
C3 C4 . 1.369(5) ?
C3 H3 . .9300 ?
C4 C5 . 1.362(5) ?
C4 C7 . 1.515(5) ?
C5 C6 . 1.376(5) ?
C5 H5 . .9300 ?
C6 H6 . .9300 ?
C7 H7A . .9600 ?
C7 H7B . .9600 ?
C7 H7C . .9600 ?
N1 C8 . 1.473(4) y
N1 H1A . .91(3) ?
N1 H1B . .93(3) ?
N1 H1C . .92(3) ?
N2 C9 . 1.127(4) y
N3 C10 . 1.120(4) y
C8 C10 . 1.469(4) y
C8 C9 . 1.473(4) y
C8 H8 . .95(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
N1 H1A O2 1_556 .91(3) 1.84(3) 2.741(4) 175(2)
N1 H1B O3 4_566 .93(3) 1.78(3) 2.701(4) 168(2)
N1 H1C O1 4_666 .92(3) 1.87(3) 2.778(5) 167(3)
C8 H8 O1 . .95(3) 2.35(2) 3.075(5) 132.3(19)
C8 H8 O2 4_666 .95(3) 2.73(2) 3.373(5) 125.8(17)
C8 H8 N2 1_655 .95(3) 2.78(3) 3.409(6) 124.2(17)
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
O3 S1 C1 C6 48.8(2)
O2 S1 C1 C6 169.4(2)
O1 S1 C1 C6 -71.1(2)
O3 S1 C1 C2 -133.3(2)
O2 S1 C1 C2 -12.7(2)
O1 S1 C1 C2 106.8(2)
C6 C1 C2 C3 -.2(4)
S1 C1 C2 C3 -178.2(2)
C1 C2 C3 C4 .3(5)
C2 C3 C4 C5 .1(5)
C2 C3 C4 C7 179.5(3)
C3 C4 C5 C6 -.5(5)
C7 C4 C5 C6 -179.9(3)
C2 C1 C6 C5 -.2(4)
S1 C1 C6 C5 177.8(2)
C4 C5 C6 C1 .5(5)
C10 C8 C9 N2 -172(8)
N1 C8 C9 N2 66(8)
C9 C8 C10 N3 7E1(4)
N1 C8 C10 N3 -17E1(10)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 489470
