# Electronic Supplementary Material (ESI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 2018

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_3C_CHO
_database_code_depnum_ccdc_archive 'CCDC 1813601'
_audit_update_record             
;
2017-12-28 deposited with the CCDC.
2018-01-26 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          489
_chemical_formula_moiety         ?
_chemical_formula_sum            'C23 H26 N2 O2 S2'
_chemical_formula_weight         426.58

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'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.41480(10)
_cell_length_b                   10.3516(3)
_cell_length_c                   14.6348(3)
_cell_angle_alpha                82.054(8)
_cell_angle_beta                 79.877(7)
_cell_angle_gamma                73.007(7)
_cell_volume                     1053.02(6)
_cell_formula_units_Z            2
_cell_measurement_temperature    123(2)
_cell_measurement_reflns_used    2775
_cell_measurement_theta_min      3.4
_cell_measurement_theta_max      26.4

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.345
_exptl_crystal_F_000             452
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.080
_exptl_crystal_size_min          0.060
_exptl_absorpt_coefficient_mu    0.275
_shelx_estimated_absorpt_T_min   0.922
_shelx_estimated_absorpt_T_max   0.984
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.912
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      123(2)
_diffrn_radiation_wavelength     0.71075
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Rotating Anode'
_diffrn_measurement_device_type  
;
RIGAKU diffractometer with FR-X generator, VariMax optics, and PILATUS 200K photon counting detector
;
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_detector_area_resol_mean 5.8140
_diffrn_reflns_number            9847
_diffrn_reflns_av_unetI/netI     0.0243
_diffrn_reflns_av_R_equivalents  0.0183
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         3.409
_diffrn_reflns_theta_max         26.397
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.969
_diffrn_measured_fraction_theta_full 0.978
_diffrn_reflns_Laue_measured_fraction_max 0.969
_diffrn_reflns_Laue_measured_fraction_full 0.978
_diffrn_reflns_point_group_measured_fraction_max 0.969
_diffrn_reflns_point_group_measured_fraction_full 0.978
_reflns_number_total             4181
_reflns_number_gt                3692
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0444P)²+0.2035P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4181
_refine_ls_number_parameters     264
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0324
_refine_ls_R_factor_gt           0.0287
_refine_ls_wR_factor_ref         0.0816
_refine_ls_wR_factor_gt          0.0796
_refine_ls_goodness_of_fit_ref   1.101
_refine_ls_restrained_S_all      1.101
_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_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
S1 S 0.16362(5) -0.19514(3) 0.78311(2) 0.01905(10) Uani 1 1 d . . . . .
C1 C -0.0180(2) -0.26571(13) 0.83431(9) 0.0201(3) Uani 1 1 d . . . . .
C2 C -0.1911(2) -0.18410(14) 0.81414(9) 0.0199(3) Uani 1 1 d . . . . .
H2 H -0.3050 -0.2060 0.8361 0.024 Uiso 1 1 calc R U . . .
C3 C -0.18137(19) -0.06344(13) 0.75683(9) 0.0167(3) Uani 1 1 d . . . . .
C4 C 0.00490(19) -0.05607(12) 0.73398(9) 0.0158(3) Uani 1 1 d . . . . .
N1 N -0.00706(15) 0.18461(10) 0.68569(7) 0.0149(2) Uani 1 1 d . . . . .
H1 H -0.1160 0.2173 0.7179 0.018 Uiso 1 1 calc R U . . .
C5 C 0.08177(18) 0.04920(12) 0.67882(9) 0.0154(3) Uani 1 1 d . . . . .
C6 C 0.25153(18) 0.03791(13) 0.61898(9) 0.0177(3) Uani 1 1 d . . . . .
H6 H 0.3390 -0.0424 0.6011 0.021 Uiso 1 1 calc R U . . .
C7 C 0.26737(18) 0.16956(13) 0.59032(9) 0.0177(3) Uani 1 1 d . . . . .
H7 H 0.3675 0.1926 0.5502 0.021 Uiso 1 1 calc R U . . .
C8 C 0.10607(18) 0.25945(13) 0.63288(9) 0.0150(3) Uani 1 1 d . . . . .
S2 S 0.24728(5) 0.47752(3) 0.59281(2) 0.01718(10) Uani 1 1 d . . . . .
C9 C 0.09431(19) 0.63898(13) 0.58577(9) 0.0175(3) Uani 1 1 d . . . . .
C10 C -0.09133(19) 0.63608(13) 0.61024(9) 0.0171(3) Uani 1 1 d . . . . .
H10 H -0.1929 0.7142 0.6117 0.020 Uiso 1 1 calc R U . . .
C11 C -0.11598(18) 0.50431(13) 0.63318(9) 0.0149(3) Uani 1 1 d . . . . .
C12 C 0.05861(18) 0.40642(13) 0.62514(9) 0.0147(3) Uani 1 1 d . . . . .
C13 C -0.31065(18) 0.48043(13) 0.65463(9) 0.0171(3) Uani 1 1 d . . . . .
H13 H -0.2982 0.3865 0.6469 0.021 Uiso 1 1 calc R U . . .
H13A H -0.3894 0.5368 0.6098 0.021 Uiso 1 1 calc R U . . .
C14 C -0.41210(19) 0.51103(13) 0.75339(9) 0.0195(3) Uani 1 1 d . . . . .
H14 H -0.4105 0.6014 0.7632 0.023 Uiso 1 1 calc R U . . .
H14A H -0.5443 0.5120 0.7568 0.023 Uiso 1 1 calc R U . . .
C15 C -0.3291(2) 0.41293(13) 0.83275(9) 0.0204(3) Uani 1 1 d . . . . .
H15 H -0.2018 0.4196 0.8340 0.024 Uiso 1 1 calc R U . . .
H15A H -0.4059 0.4413 0.8911 0.024 Uiso 1 1 calc R U . . .
N2 N -0.31814(15) 0.26874(11) 0.82740(7) 0.0166(2) Uani 1 1 d . . . . .
C16 C -0.50130(19) 0.25404(13) 0.80912(10) 0.0192(3) Uani 1 1 d . . . . .
H16 H -0.5336 0.3093 0.7520 0.023 Uiso 1 1 calc R U . . .
H16A H -0.5999 0.2902 0.8593 0.023 Uiso 1 1 calc R U . . .
C17 C -0.50470(19) 0.10980(14) 0.80010(10) 0.0208(3) Uani 1 1 d . . . . .
H17 H -0.6303 0.1126 0.7879 0.025 Uiso 1 1 calc R U . . .
H17A H -0.4853 0.0566 0.8593 0.025 Uiso 1 1 calc R U . . .
C18 C -0.35424(19) 0.03614(13) 0.72272(10) 0.0197(3) Uani 1 1 d . . . . .
H18 H -0.4146 -0.0116 0.6902 0.024 Uiso 1 1 calc R U . . .
H18A H -0.3129 0.1038 0.6780 0.024 Uiso 1 1 calc R U . . .
C19 C -0.2523(2) 0.18152(14) 0.91220(9) 0.0212(3) Uani 1 1 d . . . . .
H19 H -0.2359 0.0876 0.9004 0.025 Uiso 1 1 calc R U . . .
C20 C -0.3933(2) 0.20721(17) 1.00199(10) 0.0326(4) Uani 1 1 d . . . . .
H20 H -0.4082 0.2969 1.0182 0.049 Uiso 1 1 calc R U . . .
H20A H -0.3459 0.1418 1.0515 0.049 Uiso 1 1 calc R U . . .
H20B H -0.5144 0.1991 0.9926 0.049 Uiso 1 1 calc R U . . .
C21 C -0.0569(2) 0.19076(16) 0.92576(10) 0.0285(3) Uani 1 1 d . . . . .
H21 H 0.0282 0.1781 0.8681 0.043 Uiso 1 1 calc R U . . .
H21A H -0.0070 0.1216 0.9728 0.043 Uiso 1 1 calc R U . . .
H21B H -0.0691 0.2783 0.9449 0.043 Uiso 1 1 calc R U . . .
C22 C 0.1653(2) 0.75464(14) 0.54901(10) 0.0228(3) Uani 1 1 d . . . . .
H22 H 0.0769 0.8392 0.5444 0.027 Uiso 1 1 calc R U . . .
O1 O 0.33251(15) 0.74916(11) 0.52369(8) 0.0332(3) Uani 1 1 d . . . . .
C23 C 0.0158(2) -0.39402(14) 0.89191(10) 0.0262(3) Uani 1 1 d . . . . .
H23 H -0.0896 -0.4251 0.9174 0.031 Uiso 1 1 calc R U . . .
O2 O 0.17078(17) -0.46410(11) 0.90957(8) 0.0358(3) Uani 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
S1 C1 1.7254(14) . ?
S1 C4 1.7308(13) . ?
C1 C2 1.371(2) . ?
C1 C23 1.4518(19) . ?
C2 C3 1.4178(18) . ?
C3 C4 1.3847(18) . ?
C3 C18 1.5051(19) . ?
C4 C5 1.4567(18) . ?
N1 C5 1.3730(16) . ?
N1 C8 1.3739(16) . ?
C5 C6 1.3856(18) . ?
C6 C7 1.4019(18) . ?
C7 C8 1.3900(18) . ?
C8 C12 1.4507(17) . ?
S2 C9 1.7250(13) . ?
S2 C12 1.7308(13) . ?
C9 C10 1.3681(19) . ?
C9 C22 1.4461(18) . ?
C10 C11 1.4157(18) . ?
C11 C12 1.3890(18) . ?
C11 C13 1.5069(18) . ?
C13 C14 1.5363(18) . ?
C14 C15 1.5227(19) . ?
C15 N2 1.4833(16) . ?
N2 C16 1.4828(17) . ?
N2 C19 1.4963(17) . ?
C16 C17 1.5248(18) . ?
C17 C18 1.5511(19) . ?
C19 C21 1.528(2) . ?
C19 C20 1.5304(19) . ?
C22 O1 1.2167(18) . ?
C23 O2 1.2158(19) . ?

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
C1 S1 C4 91.61(6) . . ?
C2 C1 C23 126.48(13) . . ?
C2 C1 S1 111.06(10) . . ?
C23 C1 S1 122.45(11) . . ?
C1 C2 C3 114.18(12) . . ?
C4 C3 C2 111.10(12) . . ?
C4 C3 C18 126.38(12) . . ?
C2 C3 C18 122.44(12) . . ?
C3 C4 C5 130.30(12) . . ?
C3 C4 S1 112.05(10) . . ?
C5 C4 S1 117.63(10) . . ?
C5 N1 C8 109.04(10) . . ?
N1 C5 C6 108.08(11) . . ?
N1 C5 C4 121.90(11) . . ?
C6 C5 C4 129.85(12) . . ?
C5 C6 C7 107.50(11) . . ?
C8 C7 C6 107.52(11) . . ?
N1 C8 C7 107.84(11) . . ?
N1 C8 C12 124.21(11) . . ?
C7 C8 C12 127.95(12) . . ?
C9 S2 C12 91.55(6) . . ?
C10 C9 C22 127.89(12) . . ?
C10 C9 S2 111.07(10) . . ?
C22 C9 S2 120.76(11) . . ?
C9 C10 C11 114.44(12) . . ?
C12 C11 C10 110.84(11) . . ?
C12 C11 C13 127.01(11) . . ?
C10 C11 C13 121.95(11) . . ?
C11 C12 C8 131.36(12) . . ?
C11 C12 S2 112.06(9) . . ?
C8 C12 S2 116.43(9) . . ?
C11 C13 C14 113.91(11) . . ?
C15 C14 C13 115.98(11) . . ?
N2 C15 C14 115.20(11) . . ?
C16 N2 C15 111.29(10) . . ?
C16 N2 C19 112.04(10) . . ?
C15 N2 C19 111.69(10) . . ?
N2 C16 C17 115.72(11) . . ?
C16 C17 C18 115.16(11) . . ?
C3 C18 C17 114.83(11) . . ?
N2 C19 C21 111.10(11) . . ?
N2 C19 C20 114.80(11) . . ?
C21 C19 C20 110.59(12) . . ?
O1 C22 C9 124.66(13) . . ?
O2 C23 C1 125.30(14) . . ?

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
C4 S1 C1 C2 -0.37(10) . . . . ?
C4 S1 C1 C23 -179.41(12) . . . . ?
C23 C1 C2 C3 179.23(12) . . . . ?
S1 C1 C2 C3 0.24(15) . . . . ?
C1 C2 C3 C4 0.09(17) . . . . ?
C1 C2 C3 C18 176.78(12) . . . . ?
C2 C3 C4 C5 -178.69(12) . . . . ?
C18 C3 C4 C5 4.8(2) . . . . ?
C2 C3 C4 S1 -0.37(14) . . . . ?
C18 C3 C4 S1 -176.91(10) . . . . ?
C1 S1 C4 C3 0.43(10) . . . . ?
C1 S1 C4 C5 178.99(10) . . . . ?
C8 N1 C5 C6 -1.48(14) . . . . ?
C8 N1 C5 C4 174.23(11) . . . . ?
C3 C4 C5 N1 40.5(2) . . . . ?
S1 C4 C5 N1 -137.72(11) . . . . ?
C3 C4 C5 C6 -144.78(15) . . . . ?
S1 C4 C5 C6 36.97(18) . . . . ?
N1 C5 C6 C7 1.09(15) . . . . ?
C4 C5 C6 C7 -174.17(13) . . . . ?
C5 C6 C7 C8 -0.30(15) . . . . ?
C5 N1 C8 C7 1.29(14) . . . . ?
C5 N1 C8 C12 -178.83(12) . . . . ?
C6 C7 C8 N1 -0.60(15) . . . . ?
C6 C7 C8 C12 179.53(12) . . . . ?
C12 S2 C9 C10 1.86(11) . . . . ?
C12 S2 C9 C22 -172.51(11) . . . . ?
C22 C9 C10 C11 172.49(12) . . . . ?
S2 C9 C10 C11 -1.37(15) . . . . ?
C9 C10 C11 C12 -0.07(16) . . . . ?
C9 C10 C11 C13 -175.22(12) . . . . ?
C10 C11 C12 C8 -173.78(13) . . . . ?
C13 C11 C12 C8 1.1(2) . . . . ?
C10 C11 C12 S2 1.49(14) . . . . ?
C13 C11 C12 S2 176.32(10) . . . . ?
N1 C8 C12 C11 -27.8(2) . . . . ?
C7 C8 C12 C11 152.08(14) . . . . ?
N1 C8 C12 S2 157.12(10) . . . . ?
C7 C8 C12 S2 -23.03(18) . . . . ?
C9 S2 C12 C11 -1.93(10) . . . . ?
C9 S2 C12 C8 174.11(10) . . . . ?
C12 C11 C13 C14 107.37(15) . . . . ?
C10 C11 C13 C14 -78.32(15) . . . . ?
C11 C13 C14 C15 -70.13(15) . . . . ?
C13 C14 C15 N2 -57.10(16) . . . . ?
C14 C15 N2 C16 -48.61(15) . . . . ?
C14 C15 N2 C19 -174.66(11) . . . . ?
C15 N2 C16 C17 178.70(11) . . . . ?
C19 N2 C16 C17 -55.45(15) . . . . ?
N2 C16 C17 C18 -57.87(16) . . . . ?
C4 C3 C18 C17 -117.57(14) . . . . ?
C2 C3 C18 C17 66.26(16) . . . . ?
C16 C17 C18 C3 101.11(14) . . . . ?
C16 N2 C19 C21 176.03(11) . . . . ?
C15 N2 C19 C21 -58.34(14) . . . . ?
C16 N2 C19 C20 -57.56(15) . . . . ?
C15 N2 C19 C20 68.07(15) . . . . ?
C10 C9 C22 O1 -175.71(14) . . . . ?
S2 C9 C22 O1 -2.4(2) . . . . ?
C2 C1 C23 O2 -179.24(14) . . . . ?
S1 C1 C23 O2 -0.4(2) . . . . ?

_refine_diff_density_max         0.308
_refine_diff_density_min         -0.244
_refine_diff_density_rms         0.043

_shelxl_version_number           2013-4


_exptl_crystal_preparation       Luminescent
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_4ccho
_database_code_depnum_ccdc_archive 'CCDC 1813602'
_audit_update_record             
;
2017-12-28 deposited with the CCDC.
2018-01-26 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          416
_chemical_formula_moiety         ?
_chemical_formula_sum            'C25 H30 N2 O2 S2'
_chemical_formula_weight         454.63

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'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   P21/a

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

_cell_length_a                   10.7685(17)
_cell_length_b                   14.2394(19)
_cell_length_c                   16.386(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 108.7594(19)
_cell_angle_gamma                90.00
_cell_volume                     2379.1(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    123(2)
_cell_measurement_reflns_used    7131
_cell_measurement_theta_min      3.1
_cell_measurement_theta_max      27.5

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.40
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.269
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             968
_exptl_absorpt_coefficient_mu    0.248
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.9073
_exptl_absorpt_correction_T_max  0.9073
_exptl_absorpt_process_details   'Jacobson, R. (1998) Private communication'
_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      123(2)
_diffrn_radiation_wavelength     0.71075
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  
;
Saturn70 CCD (4x4 bin mode) with MicroMax-007
;
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            18152
_diffrn_reflns_av_R_equivalents  0.0214
_diffrn_reflns_av_sigmaI/netI    0.0211
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         3.09
_diffrn_reflns_theta_max         27.52
_reflns_number_total             5384
_reflns_number_gt                4856
_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 F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² 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/[σ²(Fo²)+(0.0438P)²+0.8955P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    none
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         5384
_refine_ls_number_parameters     282
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0388
_refine_ls_R_factor_gt           0.0342
_refine_ls_wR_factor_ref         0.0865
_refine_ls_wR_factor_gt          0.0832
_refine_ls_goodness_of_fit_ref   1.023
_refine_ls_restrained_S_all      1.023
_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
N1 N 0.11445(10) 0.51851(7) 0.26920(6) 0.0203(2) Uani 1 1 d . . .
H1 H 0.0373 0.4908 0.2531 0.024 Uiso 1 1 calc R . .
N2 N -0.37484(10) 0.45609(8) 0.23844(7) 0.0251(2) Uani 1 1 d . . .
S1 S 0.14207(3) 0.59539(2) 0.050757(19) 0.02272(9) Uani 1 1 d . . .
S2 S 0.35484(3) 0.38749(2) 0.471068(19) 0.02025(8) Uani 1 1 d . . .
O1 O 0.06413(10) 0.61744(7) -0.14750(6) 0.0326(2) Uani 1 1 d . . .
O2 O 0.47434(9) 0.25140(7) 0.62161(6) 0.0307(2) Uani 1 1 d . . .
C1 C -0.00029(13) 0.63667(9) -0.02325(8) 0.0232(3) Uani 1 1 d . . .
C2 C -0.09201(12) 0.65976(9) 0.01547(8) 0.0236(3) Uani 1 1 d . . .
H2 H -0.1765 0.6836 -0.0154 0.028 Uiso 1 1 calc R . .
C3 C -0.04908(12) 0.64478(8) 0.10545(8) 0.0211(2) Uani 1 1 d . . .
C4 C 0.07666(12) 0.60898(8) 0.13364(8) 0.0201(2) Uani 1 1 d . . .
C5 C 0.15675(12) 0.58283(8) 0.22083(8) 0.0202(2) Uani 1 1 d . . .
C6 C 0.28039(12) 0.61119(9) 0.26885(8) 0.0227(3) Uani 1 1 d . . .
H3 H 0.3331 0.6557 0.2519 0.027 Uiso 1 1 calc R . .
C7 C 0.31532(12) 0.56260(9) 0.34777(8) 0.0229(3) Uani 1 1 d . . .
H4 H 0.3956 0.5686 0.3937 0.028 Uiso 1 1 calc R . .
C8 C 0.21213(11) 0.50471(8) 0.34660(7) 0.0193(2) Uani 1 1 d . . .
C9 C 0.20605(11) 0.43604(8) 0.41090(7) 0.0190(2) Uani 1 1 d . . .
C10 C 0.10302(12) 0.40260(9) 0.43574(8) 0.0207(2) Uani 1 1 d . . .
C11 C 0.14777(12) 0.33810(9) 0.50506(8) 0.0224(2) Uani 1 1 d . . .
H5 H 0.0908 0.3079 0.5307 0.027 Uiso 1 1 calc R . .
C12 C 0.28085(12) 0.32332(9) 0.53174(7) 0.0208(2) Uani 1 1 d . . .
C13 C -0.12914(12) 0.66784(9) 0.16302(8) 0.0225(2) Uani 1 1 d . . .
H8 H -0.1688 0.7308 0.1474 0.027 Uiso 1 1 calc R . .
H9 H -0.0701 0.6709 0.2234 0.027 Uiso 1 1 calc R . .
C14 C -0.23805(13) 0.59716(9) 0.15754(8) 0.0249(3) Uani 1 1 d . . .
H10 H -0.1996 0.5335 0.1701 0.030 Uiso 1 1 calc R . .
H11 H -0.3008 0.5969 0.0982 0.030 Uiso 1 1 calc R . .
C15 C -0.31124(13) 0.62037(9) 0.22078(9) 0.0263(3) Uani 1 1 d . . .
H12 H -0.2484 0.6195 0.2801 0.032 Uiso 1 1 calc R . .
H13 H -0.3474 0.6847 0.2090 0.032 Uiso 1 1 calc R . .
C16 C -0.42277(12) 0.55211(9) 0.21549(9) 0.0276(3) Uani 1 1 d . . .
H14 H -0.4701 0.5733 0.2549 0.033 Uiso 1 1 calc R . .
H15 H -0.4856 0.5525 0.1561 0.033 Uiso 1 1 calc R . .
C17 C -0.34440(12) 0.44116(11) 0.33140(9) 0.0294(3) Uani 1 1 d . . .
H16 H -0.4277 0.4372 0.3446 0.035 Uiso 1 1 calc R . .
H17 H -0.2958 0.4965 0.3622 0.035 Uiso 1 1 calc R . .
C18 C -0.26405(13) 0.35353(11) 0.36585(9) 0.0331(3) Uani 1 1 d . . .
H18 H -0.3152 0.2979 0.3376 0.040 Uiso 1 1 calc R . .
H19 H -0.2507 0.3486 0.4284 0.040 Uiso 1 1 calc R . .
C19 C -0.13004(12) 0.35046(10) 0.35227(9) 0.0268(3) Uani 1 1 d . . .
H20 H -0.1424 0.3553 0.2899 0.032 Uiso 1 1 calc R . .
H21 H -0.0876 0.2894 0.3729 0.032 Uiso 1 1 calc R . .
C20 C -0.03959(12) 0.43043(9) 0.40023(8) 0.0238(3) Uani 1 1 d . . .
H22 H -0.0481 0.4839 0.3602 0.029 Uiso 1 1 calc R . .
H23 H -0.0692 0.4520 0.4484 0.029 Uiso 1 1 calc R . .
C21 C -0.46007(14) 0.38290(10) 0.18591(9) 0.0320(3) Uani 1 1 d . . .
H30 H -0.4192 0.3213 0.2092 0.038 Uiso 1 1 calc R . .
C22 C -0.4596(2) 0.38823(12) 0.09312(10) 0.0503(5) Uani 1 1 d . . .
H24 H -0.5012 0.4469 0.0668 0.075 Uiso 1 1 calc R . .
H25 H -0.5082 0.3348 0.0605 0.075 Uiso 1 1 calc R . .
H26 H -0.3689 0.3865 0.0924 0.075 Uiso 1 1 calc R . .
C23 C -0.60041(15) 0.38069(12) 0.19024(12) 0.0449(4) Uani 1 1 d . . .
H27 H -0.5974 0.3792 0.2506 0.067 Uiso 1 1 calc R . .
H28 H -0.6457 0.3246 0.1605 0.067 Uiso 1 1 calc R . .
H29 H -0.6477 0.4369 0.1623 0.067 Uiso 1 1 calc R . .
C24 C -0.01818(14) 0.63950(9) -0.11462(8) 0.0275(3) Uani 1 1 d . . .
H6 H -0.1008 0.6602 -0.1519 0.033 Uiso 1 1 calc R . .
C25 C 0.35558(12) 0.26239(9) 0.60072(8) 0.0240(3) Uani 1 1 d . . .
H7 H 0.3093 0.2287 0.6319 0.029 Uiso 1 1 calc R . .


_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
N1 C8 1.3768(15) . ?
N1 C5 1.3809(15) . ?
N2 C17 1.4668(17) . ?
N2 C16 1.4671(17) . ?
N2 C21 1.4702(18) . ?
S1 C1 1.7235(13) . ?
S1 C4 1.7301(12) . ?
S2 C12 1.7227(12) . ?
S2 C9 1.7323(12) . ?
O1 C24 1.2172(17) . ?
O2 C25 1.2230(16) . ?
C1 C2 1.3745(18) . ?
C1 C24 1.4474(17) . ?
C2 C3 1.4123(17) . ?
C3 C4 1.3800(17) . ?
C3 C13 1.5046(16) . ?
C4 C5 1.4598(17) . ?
C5 C6 1.3714(17) . ?
C6 C7 1.4070(17) . ?
C7 C8 1.3787(17) . ?
C8 C9 1.4543(16) . ?
C9 C10 1.3834(16) . ?
C10 C11 1.4190(17) . ?
C10 C20 1.5098(17) . ?
C11 C12 1.3734(17) . ?
C12 C25 1.4466(17) . ?
C13 C14 1.5260(18) . ?
C14 C15 1.5263(17) . ?
C15 C16 1.5257(18) . ?
C17 C18 1.520(2) . ?
C18 C19 1.5299(18) . ?
C19 C20 1.5397(18) . ?
C21 C22 1.524(2) . ?
C21 C23 1.536(2) . ?

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
C8 N1 C5 109.15(10) . . ?
C17 N2 C16 110.12(11) . . ?
C17 N2 C21 113.21(11) . . ?
C16 N2 C21 114.12(10) . . ?
C1 S1 C4 91.13(6) . . ?
C12 S2 C9 91.45(6) . . ?
C2 C1 C24 126.48(12) . . ?
C2 C1 S1 111.43(9) . . ?
C24 C1 S1 121.98(10) . . ?
C1 C2 C3 113.78(11) . . ?
C4 C3 C2 111.21(11) . . ?
C4 C3 C13 124.69(11) . . ?
C2 C3 C13 124.08(11) . . ?
C3 C4 C5 128.98(11) . . ?
C3 C4 S1 112.45(9) . . ?
C5 C4 S1 118.57(9) . . ?
C6 C5 N1 107.74(10) . . ?
C6 C5 C4 130.19(11) . . ?
N1 C5 C4 122.05(11) . . ?
C5 C6 C7 107.80(11) . . ?
C8 C7 C6 107.77(11) . . ?
N1 C8 C7 107.52(10) . . ?
N1 C8 C9 124.36(11) . . ?
C7 C8 C9 128.01(11) . . ?
C10 C9 C8 132.21(11) . . ?
C10 C9 S2 112.19(9) . . ?
C8 C9 S2 115.58(8) . . ?
C9 C10 C11 111.11(11) . . ?
C9 C10 C20 127.51(11) . . ?
C11 C10 C20 121.33(11) . . ?
C12 C11 C10 113.89(11) . . ?
C11 C12 C25 127.02(11) . . ?
C11 C12 S2 111.34(9) . . ?
C25 C12 S2 121.65(9) . . ?
C3 C13 C14 113.81(10) . . ?
C13 C14 C15 111.84(10) . . ?
C16 C15 C14 113.10(11) . . ?
N2 C16 C15 111.93(10) . . ?
N2 C17 C18 114.52(12) . . ?
C17 C18 C19 114.86(11) . . ?
C18 C19 C20 112.09(11) . . ?
C10 C20 C19 113.62(11) . . ?
N2 C21 C22 110.30(13) . . ?
N2 C21 C23 115.20(12) . . ?
C22 C21 C23 111.49(14) . . ?
O1 C24 C1 125.24(13) . . ?
O2 C25 C12 124.36(12) . . ?

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
C4 S1 C1 C2 0.27(10) . . . . ?
C4 S1 C1 C24 -176.19(11) . . . . ?
C24 C1 C2 C3 176.41(12) . . . . ?
S1 C1 C2 C3 0.14(14) . . . . ?
C1 C2 C3 C4 -0.61(16) . . . . ?
C1 C2 C3 C13 177.67(11) . . . . ?
C2 C3 C4 C5 -179.35(12) . . . . ?
C13 C3 C4 C5 2.4(2) . . . . ?
C2 C3 C4 S1 0.80(14) . . . . ?
C13 C3 C4 S1 -177.46(10) . . . . ?
C1 S1 C4 C3 -0.63(10) . . . . ?
C1 S1 C4 C5 179.51(10) . . . . ?
C8 N1 C5 C6 -1.36(13) . . . . ?
C8 N1 C5 C4 177.28(11) . . . . ?
C3 C4 C5 C6 -125.44(15) . . . . ?
S1 C4 C5 C6 54.40(17) . . . . ?
C3 C4 C5 N1 56.25(18) . . . . ?
S1 C4 C5 N1 -123.91(11) . . . . ?
N1 C5 C6 C7 0.68(14) . . . . ?
C4 C5 C6 C7 -177.82(12) . . . . ?
C5 C6 C7 C8 0.24(14) . . . . ?
C5 N1 C8 C7 1.51(13) . . . . ?
C5 N1 C8 C9 -174.84(11) . . . . ?
C6 C7 C8 N1 -1.07(14) . . . . ?
C6 C7 C8 C9 175.11(11) . . . . ?
N1 C8 C9 C10 -34.1(2) . . . . ?
C7 C8 C9 C10 150.32(14) . . . . ?
N1 C8 C9 S2 147.83(10) . . . . ?
C7 C8 C9 S2 -27.75(17) . . . . ?
C12 S2 C9 C10 -1.08(10) . . . . ?
C12 S2 C9 C8 177.39(9) . . . . ?
C8 C9 C10 C11 -177.32(12) . . . . ?
S2 C9 C10 C11 0.81(13) . . . . ?
C8 C9 C10 C20 0.0(2) . . . . ?
S2 C9 C10 C20 178.15(10) . . . . ?
C9 C10 C11 C12 -0.01(15) . . . . ?
C20 C10 C11 C12 -177.54(11) . . . . ?
C10 C11 C12 C25 179.67(12) . . . . ?
C10 C11 C12 S2 -0.80(14) . . . . ?
C9 S2 C12 C11 1.06(10) . . . . ?
C9 S2 C12 C25 -179.38(11) . . . . ?
C4 C3 C13 C14 -105.35(14) . . . . ?
C2 C3 C13 C14 76.61(15) . . . . ?
C3 C13 C14 C15 176.68(11) . . . . ?
C13 C14 C15 C16 178.76(11) . . . . ?
C17 N2 C16 C15 89.73(13) . . . . ?
C21 N2 C16 C15 -141.67(12) . . . . ?
C14 C15 C16 N2 62.79(15) . . . . ?
C16 N2 C17 C18 -165.99(11) . . . . ?
C21 N2 C17 C18 64.91(14) . . . . ?
N2 C17 C18 C19 59.80(16) . . . . ?
C17 C18 C19 C20 62.78(16) . . . . ?
C9 C10 C20 C19 114.04(14) . . . . ?
C11 C10 C20 C19 -68.87(15) . . . . ?
C18 C19 C20 C10 144.48(11) . . . . ?
C17 N2 C21 C22 -165.66(12) . . . . ?
C16 N2 C21 C22 67.31(15) . . . . ?
C17 N2 C21 C23 67.06(15) . . . . ?
C16 N2 C21 C23 -59.96(16) . . . . ?
C2 C1 C24 O1 -178.94(13) . . . . ?
S1 C1 C24 O1 -3.0(2) . . . . ?
C11 C12 C25 O2 179.61(13) . . . . ?
S2 C12 C25 O2 0.12(18) . . . . ?

_diffrn_measured_fraction_theta_max 0.983
_diffrn_reflns_theta_full        27.52
_diffrn_measured_fraction_theta_full 0.983
_refine_diff_density_max         0.283
_refine_diff_density_min         -0.263
_refine_diff_density_rms         0.041
_exptl_crystal_preparation       Luminescent
