# Electronic Supplementary Material (ESI) for Journal of Materials Chemistry A
# This journal is © The Royal Society of Chemistry 2013


#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
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# 
#  This CIF contains data from an original supplementary publication 
#  deposited with the CCDC, and may include chemical, crystal,   
#  experimental, refinement, atomic coordinates, 
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted. 
# 
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#  fide research purposes only. It may contain copyright material 
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data_1
_database_code_depnum_ccdc_archive 'CCDC 917430'
#TrackingRef '16419_web_deposit_cif_file_0_YukaKobayashi_1356417193.TTFCOONH4.cif'
#==============================================================================
# 0. AUDIT DETAILS
_audit_creation_date             'Sep 18 16:55:28 2011'
_audit_creation_method           'PLATON <TABLE ACC> option'
_audit_update_record             
;
;
_chemical_name_systematic        
;
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C7 H3 O2 S4, H4 N'
# Ex: 'C12 H16 N2 O6, H2 O' and '(Cd 2+)3, (C6 N6 Cr 3-)2, 2(H2 O)'
_chemical_formula_structural     ?
_chemical_formula_sum            'C7 H7 N O2 S4'
_chemical_formula_iupac          ?
_chemical_formula_weight         265.42
_chemical_compound_source        'see text'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
S S 0.17930 0.22050
O O 0.01750 0.01140
N N 0.01020 0.00630
H H 0.00000 0.00000
C C 0.00560 0.00310
#===============================================================================
# 6. CRYSTAL DATA
_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 21/c'
_symmetry_Int_Tables_number      14
loop_
_symmetry_equiv_pos_site_id
_symmetry_equiv_pos_as_xyz
1 x,y,z
2 -x,1/2+y,1/2-z
3 -x,-y,-z
4 x,1/2-y,1/2+z
_cell_length_a                   6.23950(10)
_cell_length_b                   3.99250(10)
_cell_length_c                   40.3716(7)
_cell_angle_alpha                90
_cell_angle_beta                 90.8189(12)
_cell_angle_gamma                90
_cell_volume                     1005.60(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    100
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?
_cell_special_details            
;
;
_exptl_crystal_description       ' ?'
_exptl_crystal_colour            ' orange'
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_crystal_size_rad          ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.753
_exptl_crystal_density_method    'Not Measured'
_exptl_crystal_F_000             544
_exptl_absorpt_coefficient_mu    2.244
_exptl_crystal_density_meas_temp ?
#------------------------------------------------------------------------------
# The next three fields give the specimen dimensions in mm. The equatorial
# plane contains the incident and diffracted beam.
_pd_spec_size_axial              ? # perpendicular to
# equatorial plane
_pd_spec_size_equat              ? # parallel to
# scattering vector
# in transmission
_pd_spec_size_thick              ? # parallel to
# scattering vector
# in reflection
#------------------------------------------------------------------------------
# The next five fields are character fields that describe the specimen.
_pd_spec_mounting                
# This field should be
# used to give details of the
# container.
; capillary
;
_pd_spec_mount_mode              transmission # options are 'reflection'
# or 'transmission'
_pd_spec_shape                   cylinder # options are 'cylinder'
# 'flat_sheet' or 'irregular'
_pd_char_particle_morphology     ?
_pd_char_colour                  ? # use ICDD colour descriptions
#------------------------------------------------------------------------------
# The following three fields describe the preparation of the specimen.
# The cooling rate is in K/min. The pressure at which the sample was
# prepared is in kPa. The temperature of preparation is in K.
_pd_prep_cool_rate               ?
_pd_prep_pressure                ?
_pd_prep_temperature             ?
#===============================================================================
# 7. EXPERIMENTAL DATA
_exptl_special_details           
;
;
_diffrn_ambient_temperature      90
_diffrn_source                   synchrotron
_diffrn_source_target            ?
_diffrn_source_type              'SPring-8 BL02B2'
_diffrn_measurement_device_type  ?
_diffrn_detector                 'Imaging Plate'
_diffrn_detector_type            ? # make or model of detector
_pd_meas_scan_method             step # options are 'step', 'cont',
# 'tof', 'fixed' or
# 'disp' (= dispersive)
_pd_meas_special_details         
;
;
#------------------------------------------------------------------------------
_diffrn_radiation_type           synchrotron
_diffrn_radiation_wavelength     0.94680
_diffrn_radiation_monochromator  Si(111)
_pd_meas_2theta_range_min        0.010
_pd_meas_2theta_range_max        78.860
_pd_meas_2theta_range_inc        0.010
_pd_meas_number_of_points        7886
#===============================================================================
# 8. REFINEMENT DATA
# Use the next field to give any special details about the fitting of the
# powder pattern.
_pd_proc_ls_special_details      
; ?
;
# The next three items are given as text.
_pd_proc_ls_profile_function     pseudo-Voigt
_pd_proc_ls_background_function  ?
_pd_proc_ls_pref_orient_corr     
; ?
;
_pd_proc_ls_prof_wR_factor       0.019
_refine_ls_R_I_factor            0.058
_refine_special_details          
;
rigid-body refinement.
;
#------------------------------------------------------------------------------
_refine_ls_structure_factor_coef Inet
_refine_ls_matrix_type           ?
_refine_ls_weighting_scheme      
? # options are 'sigma' (based on measured su's)
# or 'calc' (calculated weights)
_refine_ls_weighting_details     ?
_refine_ls_hydrogen_treatment    noref
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
#------------------------------------------------------------------------------
_refine_ls_number_parameters     ?
_refine_ls_number_constraints    ?
_refine_ls_number_restraints     0
#------------------------------------------------------------------------------
# The following item is the same as CHI, the square root of 'CHI squared'
_refine_ls_goodness_of_fit_all   ?
_refine_ls_restrained_S_all      ?
_refine_ls_shift/su_max          ?
_refine_ls_shift/su_mean         ?
#------------------------------------------------------------------------------
_pd_proc_2theta_range_min        2.000
_pd_proc_2theta_range_max        77.860
_pd_proc_2theta_range_inc        0.010
_pd_proc_wavelength              0.94680
_pd_block_diffractogram_id       ?
#------------------------------------------------------------------------------
# Give appropriate details in the next two text fields.
_pd_proc_info_excluded_regions   ?
_pd_proc_info_data_reduction     ?
# The following items are used to identify the programs used.
_computing_data_collection       ?
_computing_cell_refinement       'Synchrotron Powder(Eiji Nishibori,2007)'
_computing_data_reduction        'Synchrotron Powder'
_computing_structure_solution    ?
_computing_structure_refinement  'Synchrotron Powder'
_computing_molecular_graphics    ?
_computing_publication_material  ?
#===============================================================================
# 9. ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_thermal_displace_type
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_occupancy
_atom_site_U_iso_or_equiv
_atom_site_calc_flag
_atom_site_refinement_flags
S3 S Uiso 0.4429(7) -0.2023(6) 0.19838(8) 1.000 0.0153(3) . .
S4 S Uiso -0.0009(7) -0.2293(6) 0.17376(8) 1.000 0.0153(3) . .
S5 S Uiso 0.5822(7) 0.2056(6) 0.13166(8) 1.000 0.0153(3) . .
S6 S Uiso 0.1384(7) 0.1786(6) 0.10705(8) 1.000 0.0153(3) . .
O12 O Uiso 0.0490(18) 0.4623(4) 0.04257(6) 1.000 0.0103(6) . .
O13 O Uiso 0.3581(7) 0.6881(5) 0.03240(7) 1.000 0.0103(6) . .
C1 C Uiso 0.26184(15) -0.0962(2) 0.16651(2) 1.000 0.0110(10) . .
C2 C Uiso 0.31947(15) 0.0725(2) 0.13891(2) 1.000 0.0110(10) . .
C7 C Uiso 0.054(3) -0.4117(6) 0.21141(9) 1.000 0.0103(6) . .
C8 C Uiso 0.259(3) -0.3992(6) 0.22279(9) 1.000 0.0103(6) . .
C9 C Uiso 0.529(3) 0.3881(6) 0.09410(9) 1.000 0.0103(6) . .
C10 C Uiso 0.321(3) 0.3754(6) 0.08255(9) 1.000 0.0103(6) . .
C11 C Uiso 0.2403(12) 0.5111(5) 0.05186(7) 1.000 0.0103(6) . .
N19 N Uiso 0.75637(15) 0.9581(2) 0.02414(2) 1.000 0.044(3) . .
H14 H Uiso -0.07233(15) -0.5285(2) 0.22476(2) 1.000 0.0103(6) . .
H15 H Uiso 0.30865(15) -0.5053(2) 0.24589(2) 1.000 0.0103(6) . .
H16 H Uiso 0.65365(15) 0.5048(2) 0.08067(2) 1.000 0.0103(6) . .
H20 H Uiso 0.8155(2) 1.0297(4) 0.04284(3) 1.000 0.044(3) . .
H21 H Uiso 0.7750(2) 1.1092(4) 0.00847(3) 1.000 0.044(3) . .
H22 H Uiso 0.6179(2) 0.9257(4) 0.02701(3) 1.000 0.044(3) . .
H23 H Uiso 0.8170(2) 0.7677(4) 0.01825(3) 1.000 0.044(3) . .
#===============================================================================
# 10. MOLECULAR GEOMETRY
_geom_special_details            
;
Bond distances, angles etc. have been calculated using the
rounded fractional coordinates. All su's are estimated
from the variances of the (full) variance-covariance matrix.
The cell esds are taken into account in the estimation of
distances, angles and torsion angles
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S3 C1 1.752(4) . . yes
S3 C8 1.714(13) . . yes
S4 C1 1.752(4) . . yes
S4 C7 1.716(6) . . yes
S5 C2 1.752(4) . . yes
S5 C9 1.711(6) . . yes
S6 C2 1.752(4) . . yes
S6 C10 1.711(13) . . yes
O12 C11 1.261(13) . . yes
O13 C11 1.294(6) . . yes
N19 H20 0.8831(15) . . no
N19 H21 0.8830(16) . . no
N19 H22 0.8829(16) . . no
N19 H23 0.8832(17) . . no
C1 C2 1.3550(12) . . no
C7 C8 1.35(2) . . no
C9 C10 1.37(2) . . no
C10 C11 1.437(8) . . no
C7 H14 1.068(14) . . no
C8 H15 1.066(6) . . no
C9 H16 1.062(14) . . no
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_2
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 S3 C8 95.9(5) . . . yes
C1 S4 C7 95.8(6) . . . yes
C2 S5 C9 96.2(6) . . . yes
C2 S6 C10 96.2(5) . . . yes
H20 N19 H22 109.45(14) . . . no
H20 N19 H23 109.48(16) . . . no
H21 N19 H22 109.46(15) . . . no
H21 N19 H23 109.50(15) . . . no
H22 N19 H23 109.45(16) . . . no
H20 N19 H21 109.49(16) . . . no
S3 C1 C2 123.24(14) . . . yes
S3 C1 S4 113.52(17) . . . yes
S4 C1 C2 123.24(13) . . . yes
S6 C2 C1 123.23(14) . . . yes
S5 C2 S6 113.53(17) . . . yes
S5 C2 C1 123.24(13) . . . yes
S4 C7 C8 117.4(9) . . . yes
S3 C8 C7 117.3(4) . . . yes
S5 C9 C10 117.1(9) . . . yes
C9 C10 C11 126.6(10) . . . no
S6 C10 C9 117.0(4) . . . yes
S6 C10 C11 116.3(12) . . . yes
O12 C11 C10 121.1(8) . . . yes
O12 C11 O13 116.6(3) . . . yes
O13 C11 C10 122.3(9) . . . yes
C8 C7 H14 123.0(6) . . . no
S4 C7 H14 119.5(12) . . . no
S3 C8 H15 119.8(14) . . . no
C7 C8 H15 122.9(12) . . . no
C10 C9 H16 122.6(6) . . . no
S5 C9 H16 120.3(13) . . . no
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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C8 S3 C1 S4 0.0(2) . . . . no
C8 S3 C1 C2 -179.98(18) . . . . no
C1 S3 C8 C7 0.0(4) . . . . no
C7 S4 C1 S3 0.0(2) . . . . no
C7 S4 C1 C2 180.00(19) . . . . no
C1 S4 C7 C8 0.0(4) . . . . no
C9 S5 C2 S6 0.0(2) . . . . no
C9 S5 C2 C1 -179.98(18) . . . . no
C2 S5 C9 C10 0.0(4) . . . . no
C10 S6 C2 S5 0.0(2) . . . . no
C10 S6 C2 C1 -180.00(17) . . . . no
C2 S6 C10 C9 0.0(4) . . . . no
C2 S6 C10 C11 180.0(3) . . . . no
S3 C1 C2 S5 0.00(19) . . . . no
S3 C1 C2 S6 -180.00(16) . . . . no
S4 C1 C2 S5 180.00(16) . . . . no
S4 C1 C2 S6 0.02(18) . . . . no
S4 C7 C8 S3 0.0(5) . . . . no
S5 C9 C10 S6 0.0(5) . . . . no
S5 C9 C10 C11 -180.0(3) . . . . no
S6 C10 C11 O12 -5.5(5) . . . . no
S6 C10 C11 O13 174.5(3) . . . . no
C9 C10 C11 O12 174.5(4) . . . . no
C9 C10 C11 O13 -5.5(7) . . . . no
loop_
_geom_contact_atom_site_label_1
_geom_contact_atom_site_label_2
_geom_contact_distance
_geom_contact_site_symmetry_1
_geom_contact_site_symmetry_2
_geom_contact_publ_flag
S3 S4 3.625(6) . 1_655 no
S3 S5 3.697(4) . 1_545 no
S3 S5 3.276(4) . . no
S3 C8 3.550(7) . 1_565 no
S4 S6 3.697(4) . 1_545 no
S4 S3 3.625(6) . 1_455 no
S4 S5 3.542(5) . 1_455 no
S4 S6 3.275(4) . . no
S4 C7 3.615(4) . 1_565 no
S5 S3 3.697(4) . 1_565 no
S5 S3 3.276(4) . . no
S5 C9 3.612(4) . 1_545 no
S5 S4 3.542(5) . 1_655 no
S5 S6 3.625(6) . 1_655 no
S6 C10 3.549(7) . 1_545 no
S6 S4 3.275(4) . . no
S6 S4 3.697(4) . 1_565 no
S6 S5 3.625(6) . 1_455 no
S6 O12 2.886(4) . . no
S6 C11 3.537(4) . 1_545 no
S3 H15 2.826(4) . 2_655 no
O12 S6 2.886(4) . . no
O12 N19 2.811(7) . 1_445 no
O12 N19 2.787(7) . 1_455 no
O13 C10 3.420(4) . 1_565 no
O13 N19 2.769(3) . 3_675 no
O13 N19 2.734(4) . . no
O12 H20 2.694(6) . 1_455 no
O12 H21 2.596(8) . 1_445 no
O12 H21 2.906(5) . 3_675 no
O12 H23 2.762(4) . 3_665 no
O12 H20 2.260(8) . 1_445 no
O12 H23 2.123(8) . 1_455 no
O13 H16 2.762(4) . . no
O13 H22 1.893(4) . . no
O13 H21 2.007(3) . 3_675 no
O13 H22 2.857(3) . 3_675 no
N19 O12 2.787(7) . 1_655 no
N19 O12 2.811(7) . 1_665 no
N19 O13 2.734(4) . . no
N19 O13 2.769(3) . 3_675 no
C1 C7 3.536(7) . 1_565 no
C1 C8 3.593(3) . 1_565 no
C1 C2 3.5211(11) . 1_545 no
C2 C1 3.5211(11) . 1_565 no
C2 C9 3.538(8) . 1_545 no
C2 C10 3.595(3) . 1_545 no
C7 C1 3.536(7) . 1_545 no
C7 S4 3.615(4) . 1_545 no
C8 S3 3.550(7) . 1_545 no
C8 C1 3.593(3) . 1_545 no
C9 C2 3.538(8) . 1_565 no
C9 S5 3.612(4) . 1_565 no
C10 C2 3.595(3) . 1_565 no
C10 O13 3.420(4) . 1_545 no
C10 S6 3.549(7) . 1_565 no
C11 S6 3.537(4) . 1_565 no
C7 H14 2.998(3) . 2_555 no
C8 H14 2.846(8) . 2_555 no
C11 H22 3.060(6) . . no
C11 H21 2.869(3) . 3_675 no
C11 H23 3.058(3) . 3_665 no
H14 C8 2.846(8) . 2_545 no
H14 C7 2.998(3) . 2_545 no
H15 S3 2.826(4) . 2_645 no
H16 O13 2.762(4) . . no
H20 O12 2.694(6) . 1_655 no
H20 O12 2.260(8) . 1_665 no
H21 O12 2.596(8) . 1_665 no
H21 O12 2.906(5) . 3_675 no
H21 O13 2.007(3) . 3_675 no
H21 C11 2.869(3) . 3_675 no
H22 O13 1.893(4) . . no
H22 C11 3.060(6) . . no
H22 O13 2.857(3) . 3_675 no
H23 O12 2.123(8) . 1_655 no
H23 O12 2.762(4) . 3_665 no
H23 C11 3.058(3) . 3_665 no
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
#
#D H A D - H H...A D...A D - H...A symm(A)
#
N19 H20 O12 0.8831(15) 2.260(8) 2.811(7) 120.32(14) 1_665 yes
N19 H21 O13 0.8830(16) 2.007(3) 2.769(3) 143.83(17) 3_675 yes
N19 H22 O13 0.8829(16) 1.893(4) 2.734(4) 158.36(18) . yes
N19 H23 O12 0.8832(17) 2.123(8) 2.787(7) 131.43(13) 1_655 yes
C8 H15 S3 1.066(6) 2.826(4) 3.858(10) 163.0(9) 2_645 yes
# Loop Mechanism for Extra Tables(s)
#loop_
#_publ_manuscript_incl_extra_item
#'_geom_extra_tableA_col_1'
#'_geom_extra_tableA_col_2'
#'_geom_extra_tableA_col_3'
#'_geom_extra_table_head_A'
#'_geom_table_footnote_A'
#'_geom_extra_tableB_col_1'
#'_geom_extra_tableB_col_2'
#'_geom_extra_tableB_col_3'
#'_geom_extra_table_head_B'
#'_geom_table_footnote_B'
#
#loop_
#_geom_extra_tableA_col_1
#_geom_extra_tableA_col_2
#_geom_extra_tableA_col_3
# ? ? ?
#
#loop_
#_geom_extra_tableB_col_1
#_geom_extra_tableB_col_2
#_geom_extra_tableB_col_3
# ? ? ?
#
#_geom_table_footnote_A
#;
# ?
#;
#
#_geom_table_footnote_B
#;
# ?
#;
#
#_geom_table_footnote_A
#;
# ?
#;
#
#_geom_table_footnote_B
#;
# ?
#;
#===END