# Electronic Supplementary Material (ESI) for Journal of Materials Chemistry C.
# This journal is © The Royal Society of Chemistry 2019

data_yano054
_audit_creation_date              2018-10-12
_audit_creation_method
;
Olex2 1.2-ac3
(compiled 2017.02.24 svn.r3390 for Rigaku Oxford Diffraction, GUI svn.r5318)
;
_shelx_SHELXL_version_number      '2017/1'
_publ_contact_author_address      ?
_publ_contact_author_email        ?
_publ_contact_author_id_orcid     ?
_publ_contact_author_name         ''
_publ_contact_author_phone        ?
_publ_section_references
;
Dolomanov, O.V., Bourhis, L.J., Gildea, R.J, Howard, J.A.K. & Puschmann, H.
 (2009), J. Appl. Cryst. 42, 339-341.

Sheldrick, G.M. (2015). Acta Cryst. A71, 3-8.

Sheldrick, G.M. (2015). Acta Cryst. C71, 3-8.
;
_chemical_name_common             ?
_chemical_name_systematic         ?
_chemical_formula_moiety          '2(C7 H7 O3 S), C30 H26 N4, 2(H2 O)'
_chemical_formula_sum             'C44 H44 N4 O8 S2'
_chemical_formula_weight          820.95
_chemical_melting_point           ?
_chemical_oxdiff_formula          'C H N O S'
_chemical_oxdiff_usercomment      PyPP-TsOH-H2O
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'

_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system       'triclinic'
_space_group_IT_number            2
_space_group_name_H-M_alt         'P -1'
_space_group_name_Hall            '-P 1'
loop_
  _space_group_symop_operation_xyz
 'x, y, z'
 '-x, -y, -z'

_cell_length_a                    7.6993(4)
_cell_length_b                    11.1583(9)
_cell_length_c                    11.5390(10)
_cell_angle_alpha                 89.783(7)
_cell_angle_beta                  85.718(6)
_cell_angle_gamma                 84.804(5)
_cell_volume                      984.49(13)
_cell_formula_units_Z             1
_cell_measurement_reflns_used     2955
_cell_measurement_temperature     123
_cell_measurement_theta_max       32.0420
_cell_measurement_theta_min       2.9580
_shelx_estimated_absorpt_T_max    ?
_shelx_estimated_absorpt_T_min    ?
_exptl_absorpt_coefficient_mu     0.197
_exptl_absorpt_correction_T_max   1.00000
_exptl_absorpt_correction_T_min   0.58221
_exptl_absorpt_correction_type    multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.34a (Rigaku Oxford Diffraction, 2017)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details    ?
_exptl_crystal_colour             yellow
_exptl_crystal_colour_primary     yellow
_exptl_crystal_density_diffrn     1.385
_exptl_crystal_density_meas       ?
_exptl_crystal_density_method     ?
_exptl_crystal_description        plate
_exptl_crystal_F_000              432
_exptl_crystal_size_max           0.2
_exptl_crystal_size_mid           0.2
_exptl_crystal_size_min           0.1
_exptl_transmission_factor_max    ?
_exptl_transmission_factor_min    ?
_diffrn_reflns_av_R_equivalents   0.0376
_diffrn_reflns_av_unetI/netI      0.0546
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max        9
_diffrn_reflns_limit_h_min        -9
_diffrn_reflns_limit_k_max        13
_diffrn_reflns_limit_k_min        -13
_diffrn_reflns_limit_l_max        14
_diffrn_reflns_limit_l_min        -14
_diffrn_reflns_number             8832
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full         25.242
_diffrn_reflns_theta_max          26.371
_diffrn_reflns_theta_min          2.544
_diffrn_ambient_temperature       123
_diffrn_detector                  'CCD plate'
_diffrn_detector_area_resol_mean  ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
--------------------------------------------------------------------------
  1  ω    -74.00 119.00   1.00   73.25    --   30.00  54.00 -30.00  193
  2  ω    -71.00  33.00   1.00   73.25    --   30.00  54.00  90.00  104
  3  ω    -73.00  31.00   1.00   73.25    --   30.00  54.00-150.00  104
  4  ω    -72.00  32.00   1.00   73.25    --   30.00  54.00 -30.00  104
;
_diffrn_measurement_device        'two-circle diffractometer'
_diffrn_measurement_device_type   'XtaLAB Mini (JP)'
_diffrn_measurement_method        'ω scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11       0.0058980000
_diffrn_orient_matrix_UB_12       -0.0636985000
_diffrn_orient_matrix_UB_13       0.0035126000
_diffrn_orient_matrix_UB_21       -0.0874019000
_diffrn_orient_matrix_UB_22       0.0004152000
_diffrn_orient_matrix_UB_23       -0.0156602000
_diffrn_orient_matrix_UB_31       0.0305152000
_diffrn_orient_matrix_UB_32       -0.0040671000
_diffrn_orient_matrix_UB_33       -0.0595162000
_diffrn_oxdiff_ac3_digest_frames
;
01b12d77bf5794ae09b76e4878bf49140800505aee4
;
_diffrn_oxdiff_ac3_digest_hkl
;
01cadc1112742108e167655b9fafb5282243a5
;
_diffrn_radiation_monochromator   graphite
_diffrn_radiation_probe           x-ray
_diffrn_radiation_type            MoK\a
_diffrn_radiation_wavelength      0.71073
_diffrn_source                    'fine-focus sealed X-ray tube'
_diffrn_source_type               'Rigaku (Mo) X-ray Source'
_reflns_Friedel_coverage          0.000
_reflns_Friedel_fraction_full     .
_reflns_Friedel_fraction_max      .
_reflns_number_gt                 2978
_reflns_number_total              4029
_reflns_odcompleteness_completeness 99.95
_reflns_odcompleteness_iscentric  1
_reflns_odcompleteness_theta      26.32
_reflns_special_details
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression      'I > 2σ(I)'
_computing_cell_refinement        'CrysAlisPro 1.171.39.34a (Rigaku OD, 2017)'
_computing_data_collection        'CrysAlisPro 1.171.39.34a (Rigaku OD, 2017)'
_computing_data_reduction         'CrysAlisPro 1.171.39.34a (Rigaku OD, 2017)'
_computing_molecular_graphics     'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material   'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement   'ShelXL (Sheldrick, 2015)'
_computing_structure_solution     'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max          0.343
_refine_diff_density_min          -0.459
_refine_diff_density_rms          0.069
_refine_ls_extinction_coef        .
_refine_ls_extinction_method      none
_refine_ls_goodness_of_fit_ref    1.085
_refine_ls_hydrogen_treatment     mixed
_refine_ls_matrix_type            full
_refine_ls_number_parameters      271
_refine_ls_number_reflns          4029
_refine_ls_number_restraints      0
_refine_ls_R_factor_all           0.0832
_refine_ls_R_factor_gt            0.0543
_refine_ls_restrained_S_all       1.085
_refine_ls_shift/su_max           0.000
_refine_ls_shift/su_mean          0.000
_refine_ls_structure_factor_coef  Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0650P)²+0.7200P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme       calc
_refine_ls_wR_factor_gt           0.1305
_refine_ls_wR_factor_ref          0.1547
_refine_special_details           ?
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H,H) groups
2.a Free rotating group:
 O1B(H1BA,H1BB)
2.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C5(H5), C6A(H6A), C7(H7), C5A(H5A), C8(H8), C2A(H2A), C10(H10),
 C6(H6), C14(H14), C13(H13), C3A(H3A), C11(H11)
2.c Idealised Me refined as rotating group:
 C7A(H7AA,H7AB,H7AC), C15(H15A,H15B,H15C)
;
_atom_sites_solution_hydrogens    mixed
_atom_sites_solution_primary      dual
_atom_sites_solution_secondary    ?
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_site_symmetry_order
  _atom_site_calc_flag
  _atom_site_refinement_flags_posn
  _atom_site_refinement_flags_adp
  _atom_site_refinement_flags_occupancy
  _atom_site_disorder_assembly
  _atom_site_disorder_group
 S1A S 0.21240(9) 0.54166(6) 0.70667(6) 0.0262(2) Uani 1 1 d . . . . .
 O2A O 0.3739(3) 0.51020(19) 0.63524(17) 0.0314(5) Uani 1 1 d . . . . .
 O3A O 0.1111(3) 0.64460(18) 0.66120(18) 0.0330(5) Uani 1 1 d . . . . .
 O1A O 0.1114(3) 0.43955(19) 0.72819(18) 0.0348(5) Uani 1 1 d . . . . .
 N1 N 0.8463(3) 0.0087(2) 0.39793(19) 0.0226(5) Uani 1 1 d . . . . .
 O1B O -0.1671(3) 0.4328(2) 0.5839(2) 0.0424(6) Uani 1 1 d . . . . .
 H1BA H -0.134214 0.398658 0.519198 0.064 Uiso 1 1 d G . . . .
 H1BB H -0.079636 0.435247 0.624339 0.064 Uiso 1 1 d G . . . .
 N2 N 0.3830(3) 0.3262(2) 0.4817(2) 0.0297(6) Uani 1 1 d . . . . .
 C3 C 0.8519(3) 0.1130(2) 0.5667(2) 0.0230(6) Uani 1 1 d . . . . .
 H3 H 0.821119 0.166964 0.629904 0.028 Uiso 1 1 calc R . . . .
 C2 C 0.7592(3) 0.0979(2) 0.4712(2) 0.0216(6) Uani 1 1 d . . . . .
 C1 C 0.9978(3) -0.0310(2) 0.4494(2) 0.0225(6) Uani 1 1 d . . . . .
 C9 C 0.8224(3) -0.0127(2) 0.2790(2) 0.0228(6) Uani 1 1 d . . . . .
 C4 C 0.5871(3) 0.1572(2) 0.4493(2) 0.0231(6) Uani 1 1 d . . . . .
 C5 C 0.5397(3) 0.2697(2) 0.4981(2) 0.0257(6) Uani 1 1 d . . . . .
 H5 H 0.618478 0.306617 0.543195 0.031 Uiso 1 1 calc R . . . .
 C1A C 0.2751(3) 0.5860(2) 0.8426(2) 0.0240(6) Uani 1 1 d . . . . .
 C6A C 0.1515(4) 0.5965(3) 0.9366(2) 0.0283(6) Uani 1 1 d . . . . .
 H6A H 0.034446 0.580270 0.926875 0.034 Uiso 1 1 calc R . . . .
 C7 C 0.3043(3) 0.1696(3) 0.3705(2) 0.0274(6) Uani 1 1 d . . . . .
 H7 H 0.221795 0.135010 0.326666 0.033 Uiso 1 1 calc R . . . .
 C5A C 0.1973(4) 0.6303(3) 1.0438(2) 0.0290(6) Uani 1 1 d . . . . .
 H5A H 0.112458 0.634600 1.108161 0.035 Uiso 1 1 calc R . . . .
 C4A C 0.3672(4) 0.6583(2) 1.0591(2) 0.0267(6) Uani 1 1 d . . . . .
 C8 C 0.4653(3) 0.1068(3) 0.3860(2) 0.0253(6) Uani 1 1 d . . . . .
 H8 H 0.492224 0.028827 0.353078 0.030 Uiso 1 1 calc R . . . .
 C2A C 0.4455(4) 0.6126(3) 0.8561(2) 0.0268(6) Uani 1 1 d . . . . .
 H2A H 0.530933 0.606291 0.792127 0.032 Uiso 1 1 calc R . . . .
 C10 C 0.7963(3) 0.0821(2) 0.2041(2) 0.0255(6) Uani 1 1 d . . . . .
 H10 H 0.793244 0.162496 0.231540 0.031 Uiso 1 1 calc R . . . .
 C6 C 0.2660(4) 0.2806(3) 0.4185(3) 0.0302(7) Uani 1 1 d . . . . .
 H6 H 0.157537 0.325302 0.407245 0.036 Uiso 1 1 calc R . . . .
 C14 C 0.8314(3) -0.1301(3) 0.2387(2) 0.0258(6) Uani 1 1 d . . . . .
 H14 H 0.849830 -0.195656 0.290536 0.031 Uiso 1 1 calc R . . . .
 C13 C 0.8133(4) -0.1509(3) 0.1223(3) 0.0295(6) Uani 1 1 d . . . . .
 H13 H 0.822003 -0.231299 0.094232 0.035 Uiso 1 1 calc R . . . .
 C3A C 0.4886(4) 0.6484(3) 0.9639(2) 0.0291(6) Uani 1 1 d . . . . .
 H3A H 0.604910 0.666713 0.973097 0.035 Uiso 1 1 calc R . . . .
 C12 C 0.7827(3) -0.0564(3) 0.0458(2) 0.0298(7) Uani 1 1 d . . . . .
 C11 C 0.7747(4) 0.0597(3) 0.0889(2) 0.0304(7) Uani 1 1 d . . . . .
 H11 H 0.753671 0.125574 0.037913 0.036 Uiso 1 1 calc R . . . .
 C7A C 0.4152(4) 0.6986(3) 1.1765(3) 0.0367(7) Uani 1 1 d . . . . .
 H7AA H 0.395583 0.786463 1.182256 0.055 Uiso 1 1 calc GR . . . .
 H7AB H 0.538703 0.673414 1.185568 0.055 Uiso 1 1 calc GR . . . .
 H7AC H 0.342426 0.662103 1.237819 0.055 Uiso 1 1 calc GR . . . .
 C15 C 0.7595(4) -0.0799(3) -0.0804(3) 0.0401(8) Uani 1 1 d . . . . .
 H15A H 0.822400 -0.157275 -0.103865 0.060 Uiso 1 1 calc GR . . . .
 H15B H 0.806272 -0.015515 -0.127962 0.060 Uiso 1 1 calc GR . . . .
 H15C H 0.634880 -0.081989 -0.091429 0.060 Uiso 1 1 calc GR . . . .
 H2 H 0.357(4) 0.392(3) 0.515(3) 0.033(9) Uiso 1 1 d . . . . .


_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
 S1A O2A 1.456(2) . ?
 S1A O3A 1.448(2) . ?
 S1A O1A 1.447(2) . ?
 S1A C1A 1.761(3) . ?
 N1 C2 1.398(3) . ?
 N1 C1 1.384(3) . ?
 N1 C9 1.422(3) . ?
 O1B H1BA 0.8501 . ?
 O1B H1BB 0.8500 . ?
 N2 C5 1.336(4) . ?
 N2 C6 1.337(4) . ?
 N2 H2 0.83(3) . ?
 C3 H3 0.9500 . ?
 C3 C2 1.376(4) . ?
 C3 C1 1.410(4) 2_756 ?
 C2 C4 1.466(3) . ?
 C1 C1 1.364(5) 2_756 ?
 C9 C10 1.373(4) . ?
 C9 C14 1.386(4) . ?
 C4 C5 1.384(4) . ?
 C4 C8 1.390(4) . ?
 C5 H5 0.9500 . ?
 C1A C6A 1.387(4) . ?
 C1A C2A 1.391(4) . ?
 C6A H6A 0.9500 . ?
 C6A C5A 1.374(4) . ?
 C7 H7 0.9500 . ?
 C7 C8 1.391(4) . ?
 C7 C6 1.358(4) . ?
 C5A H5A 0.9500 . ?
 C5A C4A 1.396(4) . ?
 C4A C3A 1.386(4) . ?
 C4A C7A 1.511(4) . ?
 C8 H8 0.9500 . ?
 C2A H2A 0.9500 . ?
 C2A C3A 1.380(4) . ?
 C10 H10 0.9500 . ?
 C10 C11 1.379(4) . ?
 C6 H6 0.9500 . ?
 C14 H14 0.9500 . ?
 C14 C13 1.384(4) . ?
 C13 H13 0.9500 . ?
 C13 C12 1.387(4) . ?
 C3A H3A 0.9500 . ?
 C12 C11 1.384(4) . ?
 C12 C15 1.507(4) . ?
 C11 H11 0.9500 . ?
 C7A H7AA 0.9800 . ?
 C7A H7AB 0.9800 . ?
 C7A H7AC 0.9800 . ?
 C15 H15A 0.9800 . ?
 C15 H15B 0.9800 . ?
 C15 H15C 0.9800 . ?

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
 O2A S1A C1A 106.14(12) . . ?
 O3A S1A O2A 112.01(12) . . ?
 O3A S1A C1A 106.41(12) . . ?
 O1A S1A O2A 112.37(13) . . ?
 O1A S1A O3A 112.85(12) . . ?
 O1A S1A C1A 106.48(13) . . ?
 C2 N1 C9 128.0(2) . . ?
 C1 N1 C2 106.4(2) . . ?
 C1 N1 C9 122.8(2) . . ?
 H1BA O1B H1BB 109.4 . . ?
 C5 N2 C6 123.5(3) . . ?
 C5 N2 H2 117(2) . . ?
 C6 N2 H2 119(2) . . ?
 C2 C3 H3 127.4 . . ?
 C2 C3 C1 105.1(2) . 2_756 ?
 C1 C3 H3 127.4 2_756 . ?
 N1 C2 C4 122.6(2) . . ?
 C3 C2 N1 110.4(2) . . ?
 C3 C2 C4 126.8(2) . . ?
 N1 C1 C3 141.9(2) . 2_756 ?
 C1 C1 N1 108.5(3) 2_756 . ?
 C1 C1 C3 109.6(3) 2_756 2_756 ?
 C10 C9 N1 120.2(2) . . ?
 C10 C9 C14 120.4(3) . . ?
 C14 C9 N1 119.3(2) . . ?
 C5 C4 C2 118.0(2) . . ?
 C5 C4 C8 117.5(2) . . ?
 C8 C4 C2 124.5(3) . . ?
 N2 C5 C4 119.9(3) . . ?
 N2 C5 H5 120.0 . . ?
 C4 C5 H5 120.0 . . ?
 C6A C1A S1A 119.2(2) . . ?
 C6A C1A C2A 119.8(3) . . ?
 C2A C1A S1A 120.9(2) . . ?
 C1A C6A H6A 119.8 . . ?
 C5A C6A C1A 120.4(3) . . ?
 C5A C6A H6A 119.8 . . ?
 C8 C7 H7 120.2 . . ?
 C6 C7 H7 120.2 . . ?
 C6 C7 C8 119.5(3) . . ?
 C6A C5A H5A 119.7 . . ?
 C6A C5A C4A 120.7(3) . . ?
 C4A C5A H5A 119.7 . . ?
 C5A C4A C7A 120.3(3) . . ?
 C3A C4A C5A 118.1(3) . . ?
 C3A C4A C7A 121.6(3) . . ?
 C4 C8 C7 120.5(3) . . ?
 C4 C8 H8 119.7 . . ?
 C7 C8 H8 119.7 . . ?
 C1A C2A H2A 120.5 . . ?
 C3A C2A C1A 119.0(3) . . ?
 C3A C2A H2A 120.5 . . ?
 C9 C10 H10 120.3 . . ?
 C9 C10 C11 119.5(3) . . ?
 C11 C10 H10 120.3 . . ?
 N2 C6 C7 119.0(3) . . ?
 N2 C6 H6 120.5 . . ?
 C7 C6 H6 120.5 . . ?
 C9 C14 H14 120.4 . . ?
 C13 C14 C9 119.3(3) . . ?
 C13 C14 H14 120.4 . . ?
 C14 C13 H13 119.4 . . ?
 C14 C13 C12 121.2(3) . . ?
 C12 C13 H13 119.4 . . ?
 C4A C3A H3A 119.0 . . ?
 C2A C3A C4A 121.9(3) . . ?
 C2A C3A H3A 119.0 . . ?
 C13 C12 C15 120.9(3) . . ?
 C11 C12 C13 118.0(3) . . ?
 C11 C12 C15 121.2(3) . . ?
 C10 C11 C12 121.6(3) . . ?
 C10 C11 H11 119.2 . . ?
 C12 C11 H11 119.2 . . ?
 C4A C7A H7AA 109.5 . . ?
 C4A C7A H7AB 109.5 . . ?
 C4A C7A H7AC 109.5 . . ?
 H7AA C7A H7AB 109.5 . . ?
 H7AA C7A H7AC 109.5 . . ?
 H7AB C7A H7AC 109.5 . . ?
 C12 C15 H15A 109.5 . . ?
 C12 C15 H15B 109.5 . . ?
 C12 C15 H15C 109.5 . . ?
 H15A C15 H15B 109.5 . . ?
 H15A C15 H15C 109.5 . . ?
 H15B C15 H15C 109.5 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.346
_oxdiff_exptl_absorpt_empirical_full_min 0.802
