# Supplementary Material (ESI) for Chemical Communications
# This journal is © The Royal Society of Chemistry 2004

data_global

_journal_coden_Cambridge         182

_publ_contact_author_name        'Professor Gautam R. Desiraju'
_publ_contact_author_address     
;
School of Chemistry
University of Hyderabad
Hyderabad 500 046
India
;
_publ_contact_author_phone       '91 40 3010567'
_publ_contact_author_fax         '91 40 3010567'
_publ_contact_author_email       desiraju@uohyd.ernet.in
_publ_requested_journal          'Chemical Communications'

# TITLE AND AUTHOR LIST

_publ_section_title              
;
Proton transfer and N(+)-H...S(-) hydrogen bonds in the crystal structure of
4-aminothiophenol
;

loop_
_publ_author_name
'Gautam Radhakrishna Desiraju'
'Roland Boese'
'Ram K. R. Jetti'
'Tejender S. Thakur'
'Venu R. Vangala'

data_cc_atpdjum
_database_code_depnum_ccdc_archive 'CCDC 238927'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
4-aminothiphenol
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C6 H7 N S'
_chemical_formula_sum            'C6 H7 N S'
_chemical_formula_weight         125.19

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'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   Pc
_symmetry_space_group_name_Hall  'P -2yc'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'x, -y, z+1/2'

_cell_length_a                   7.2305(12)
_cell_length_b                   5.8513(10)
_cell_length_c                   7.7552(13)
_cell_angle_alpha                90.00
_cell_angle_beta                 107.364(3)
_cell_angle_gamma                90.00
_cell_volume                     313.15(9)
_cell_formula_units_Z            2
_cell_measurement_temperature    203(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       Plate
_exptl_crystal_colour            'pale yellow'
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.05
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_diffrn    1.328
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             132
_exptl_absorpt_coefficient_mu    0.399
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  .
_exptl_absorpt_correction_T_max  .
_exptl_absorpt_process_details   .

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      203(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker SMART CCD area detector'
_diffrn_measurement_method       \w
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count .
_diffrn_standards_interval_time  .
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            3386
_diffrn_reflns_av_R_equivalents  0.0201
_diffrn_reflns_av_sigmaI/netI    0.0240
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         3.48
_diffrn_reflns_theta_max         28.31
_reflns_number_total             1518
_reflns_number_gt                1474
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
;
Refinement of F^2^ against ALL reflections.  The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement.  R-factors based
on F^2^ are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[\s^2^(Fo^2^)+(0.0495P)^2^+0.0301P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.02(8)
_refine_ls_number_reflns         1518
_refine_ls_number_parameters     86
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0283
_refine_ls_R_factor_gt           0.0277
_refine_ls_wR_factor_ref         0.0767
_refine_ls_wR_factor_gt          0.0757
_refine_ls_goodness_of_fit_ref   1.072
_refine_ls_restrained_S_all      1.071
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.80444(8) 0.25977(4) 0.87161(8) 0.03666(12) Uani 1 1 d . . .
N1 N -0.0591(2) 0.24134(18) 0.5232(2) 0.0332(3) Uani 1 1 d . . .
H1A H -0.111(5) 0.387(6) 0.446(4) 0.083(9) Uiso 1 1 d . . .
H1B H -0.105(4) 0.100(5) 0.451(3) 0.060(7) Uiso 1 1 d . . .
H1C H -0.104(5) 0.241(3) 0.621(4) 0.058(9) Uiso 1 1 d . . .
C1 C 0.5529(2) 0.25635(17) 0.76446(19) 0.0263(3) Uani 1 1 d . . .
C2 C 0.4341(2) 0.4324(2) 0.7939(2) 0.0334(3) Uani 1 1 d . . .
H2 H 0.4900 0.5549 0.8701 0.040 Uiso 1 1 d R . .
C3 C 0.2354(2) 0.4285(2) 0.7125(2) 0.0345(3) Uani 1 1 d . . .
H3 H 0.1575 0.5475 0.7333 0.041 Uiso 1 1 d R . .
C4 C 0.1518(2) 0.24712(18) 0.5996(2) 0.0277(3) Uani 1 1 d . . .
C5 C 0.2662(2) 0.0728(2) 0.5663(2) 0.0333(3) Uani 1 1 d . . .
H5 H 0.2095 -0.0484 0.4890 0.040 Uiso 1 1 d R . .
C6 C 0.4659(2) 0.0784(2) 0.64831(18) 0.0332(3) Uani 1 1 d . . .
H6 H 0.5434 -0.0396 0.6251 0.040 Uiso 1 1 d R . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
S1 0.02212(17) 0.03094(17) 0.0511(2) -0.00121(16) 0.00207(12) -0.00031(15)
N1 0.0210(7) 0.0283(6) 0.0460(7) 0.0005(4) 0.0033(6) 0.0017(3)
C1 0.0212(7) 0.0250(7) 0.0313(6) 0.0019(4) 0.0055(5) -0.0001(4)
C2 0.0309(7) 0.0259(6) 0.0416(7) -0.0069(5) 0.0077(6) -0.0006(5)
C3 0.0295(6) 0.0290(6) 0.0440(7) -0.0062(5) 0.0094(6) 0.0022(5)
C4 0.0215(7) 0.0250(6) 0.0340(6) 0.0016(4) 0.0043(5) 0.0008(4)
C5 0.0288(6) 0.0289(6) 0.0391(7) -0.0062(5) 0.0052(6) -0.0005(4)
C6 0.0292(7) 0.0271(6) 0.0424(8) -0.0053(5) 0.0096(6) 0.0016(5)

_geom_special_details            
;
All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix.  The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry.  An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;

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 C1 1.7598(17) . ?
N1 C4 1.462(2) . ?
N1 H1A 1.05(3) . ?
N1 H1B 1.00(3) . ?
N1 H1C 0.91(3) . ?
C1 C6 1.3977(18) . ?
C1 C2 1.4031(19) . ?
C2 C3 1.3860(19) . ?
C2 H2 0.9400 . ?
C3 C4 1.3937(19) . ?
C3 H3 0.9400 . ?
C4 C5 1.385(2) . ?
C5 C6 1.3934(18) . ?
C5 H5 0.9400 . ?
C6 H6 0.9400 . ?

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
_geom_angle_publ_flag
C4 N1 H1A 112(2) . . ?
C4 N1 H1B 112.4(17) . . ?
H1A N1 H1B 111(3) . . ?
C4 N1 H1C 105(2) . . ?
H1A N1 H1C 109(3) . . ?
H1B N1 H1C 108(2) . . ?
C6 C1 C2 118.18(15) . . ?
C6 C1 S1 121.06(10) . . ?
C2 C1 S1 120.77(11) . . ?
C3 C2 C1 121.01(13) . . ?
C3 C2 H2 119.5 . . ?
C1 C2 H2 119.5 . . ?
C2 C3 C4 119.67(13) . . ?
C2 C3 H3 120.2 . . ?
C4 C3 H3 120.2 . . ?
C5 C4 C3 120.45(16) . . ?
C5 C4 N1 121.06(12) . . ?
C3 C4 N1 118.44(12) . . ?
C4 C5 C6 119.50(13) . . ?
C4 C5 H5 120.2 . . ?
C6 C5 H5 120.3 . . ?
C5 C6 C1 121.17(12) . . ?
C5 C6 H6 119.4 . . ?
C1 C6 H6 119.4 . . ?

_diffrn_measured_fraction_theta_max 0.992
_diffrn_reflns_theta_full        28.31
_diffrn_measured_fraction_theta_full 0.992
_refine_diff_density_max         0.237
_refine_diff_density_min         -0.164
_refine_diff_density_rms         0.045