# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2015

####################################################################### 
# 
# 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_fs774
_database_code_depnum_ccdc_archive 'CCDC 1406084'
_audit_update_record             
;
2015-06-11 deposited with the CCDC.
2015-07-23 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
2,2'-disulfanediylbis(4,5,6,7,8,9-hexahydro-1H-cycloocta[b]pyrrole-3-carbonitrile)
_chemical_name_common            
2,2'-disulfanediylbis(4,5,6,7,8,9-hexahydro-1H-cycloocta[b]pyrrole-3-carbonitrile)
_chemical_melting_point          499-500
_chemical_formula_moiety         'C22 H26 N4 S2'
_chemical_formula_sum            'C22 H26 N4 S2'
_chemical_formula_weight         410.59

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           ORTHORHOMBIC
_symmetry_space_group_name_H-M   'p bna'

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

_cell_length_a                   9.6655(3)
_cell_length_b                   13.8908(6)
_cell_length_c                   16.1834(7)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     2172.81(15)
_cell_formula_units_Z            4
_cell_measurement_temperature    295(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       prism
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          .14
_exptl_crystal_size_mid          .1
_exptl_crystal_size_min          .08
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.255
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             872
_exptl_absorpt_coefficient_mu    2.325
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
[c.f. r.h. blessing, acta cryst. (1995), a51, 33-38]
;

_exptl_absorpt_correction_T_min  0.750
_exptl_absorpt_correction_T_max  0.884


_exptl_special_details           
;
 ?
;
_diffrn_detector                 Pilatus100K
_diffrn_measurement_device_type  STOE
_diffrn_detector_area_resol_mean 5.81
_diffrn_source                   'Cu GeniX 3D'
_diffrn_source_voltage           50
_diffrn_source_current           0.600
_diffrn_source_power             0.030
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54186
_diffrn_radiation_monochromator  none
_diffrn_radiation_polarisn_norm  0
_diffrn_radiation_collimation    'focusing mirrors'
_diffrn_ambient_temperature      295
_diffrn_measurement_method       'rotation method'
_diffrn_measurement_details      
; 2361 frames, detector distance = 42 mm
;

_diffrn_standards_decay_%        0
_diffrn_reflns_number            8748
_diffrn_reflns_av_R_equivalents  0.1183
_diffrn_reflns_av_sigmaI/netI    0.1424
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         5.33
_diffrn_reflns_theta_max         72.73
_reflns_number_total             2154
_reflns_number_gt                1692
_reflns_threshold_expression     >2sigma(I)
_computing_data_collection       'STOE X-AREA'
_computing_cell_refinement       'STOE X-AREA'
_computing_data_reduction        'STOE X-RED'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_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)+(0.0001P)²+0.0000P] where P=(Fo²+2Fc²)/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     SHELXL
_refine_ls_extinction_coef       0.00052(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2154
_refine_ls_number_parameters     132
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1533
_refine_ls_R_factor_gt           0.0405
_refine_ls_wR_factor_ref         0.0768
_refine_ls_wR_factor_gt          0.0594
_refine_ls_goodness_of_fit_ref   0.969
_refine_ls_restrained_S_all      0.969
_refine_ls_shift/su_max          0.000
_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 0.14336(9) 0.27226(6) 0.43811(6) 0.0670(3) Uani 1 1 d . . .
N1 N -0.0355(3) 0.1327(2) 0.38149(19) 0.0574(7) Uani 1 1 d . . .
N2 N -0.1488(4) 0.4624(2) 0.3936(2) 0.0937(10) Uani 1 1 d . . .
C2 C -0.0095(3) 0.2266(2) 0.3995(2) 0.0538(8) Uani 1 1 d . . .
C3 C -0.1252(3) 0.2779(2) 0.37546(19) 0.0510(8) Uani 1 1 d . . .
C4 C -0.2208(4) 0.2140(2) 0.34012(19) 0.0555(9) Uani 1 1 d . . .
C5 C -0.1638(4) 0.1234(2) 0.34546(19) 0.0572(9) Uani 1 1 d . . .
C6 C -0.2208(4) 0.0289(2) 0.3201(3) 0.0830(12) Uani 1 1 d . . .
H6A H -0.1456 -0.0173 0.3189 0.100 Uiso 1 1 calc R . .
H6B H -0.2559 0.0348 0.2642 0.100 Uiso 1 1 calc R . .
C7 C -0.3340(4) -0.0110(2) 0.3736(3) 0.0954(13) Uani 1 1 d . . .
H7A H -0.2998 -0.0138 0.4300 0.114 Uiso 1 1 calc R . .
H7B H -0.3518 -0.0766 0.3562 0.114 Uiso 1 1 calc R . .
C8 C -0.4697(5) 0.0422(3) 0.3744(4) 0.1243(18) Uani 1 1 d . . .
H8A H -0.4967 0.0527 0.3173 0.149 Uiso 1 1 calc R . .
H8B H -0.5383 -0.0002 0.3986 0.149 Uiso 1 1 calc R . .
C9 C -0.4789(4) 0.1341(4) 0.4168(3) 0.1169(18) Uani 1 1 d . . .
H9A H -0.4024 0.1377 0.4555 0.140 Uiso 1 1 calc R . .
H9B H -0.5634 0.1340 0.4491 0.140 Uiso 1 1 calc R . .
C10 C -0.4775(4) 0.2258(3) 0.3652(3) 0.0905(13) Uani 1 1 d . . .
H10A H -0.5633 0.2289 0.3343 0.109 Uiso 1 1 calc R . .
H10B H -0.4762 0.2804 0.4026 0.109 Uiso 1 1 calc R . .
C11 C -0.3599(4) 0.2368(2) 0.3056(2) 0.0765(10) Uani 1 1 d . . .
H11A H -0.3767 0.1951 0.2586 0.092 Uiso 1 1 calc R . .
H11B H -0.3591 0.3025 0.2856 0.092 Uiso 1 1 calc R . .
C12 C -0.1384(4) 0.3794(3) 0.3846(2) 0.0686(9) Uani 1 1 d . . .
H1 H 0.034(3) 0.075(2) 0.3886(19) 0.074(10) Uiso 1 1 d . . .

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 0.0514(5) 0.0621(5) 0.0875(6) -0.0003(6) 0.0097(6) -0.0104(5)
N1 0.060(2) 0.0437(18) 0.068(2) -0.0070(17) 0.0082(18) 0.0010(16)
N2 0.085(2) 0.0506(18) 0.146(3) -0.005(2) -0.021(3) -0.001(2)
C2 0.060(2) 0.0462(19) 0.055(2) -0.004(2) 0.0097(16) -0.008(2)
C3 0.057(2) 0.0407(18) 0.055(2) 0.005(2) -0.0011(19) 0.000(2)
C4 0.058(2) 0.049(2) 0.059(2) -0.001(2) -0.0053(19) -0.0064(19)
C5 0.060(3) 0.051(2) 0.061(2) -0.0068(18) 0.0010(19) -0.012(2)
C6 0.086(3) 0.055(3) 0.108(3) -0.020(2) 0.000(3) -0.008(2)
C7 0.086(3) 0.055(2) 0.145(4) 0.002(3) 0.014(3) -0.007(2)
C8 0.092(4) 0.092(4) 0.189(6) 0.022(4) 0.024(4) -0.009(3)
C9 0.091(3) 0.094(3) 0.166(6) 0.007(4) 0.039(3) -0.001(3)
C10 0.071(3) 0.070(3) 0.131(4) 0.011(3) -0.019(3) 0.006(2)
C11 0.091(3) 0.058(2) 0.080(3) 0.011(2) -0.026(3) -0.011(3)
C12 0.060(2) 0.061(2) 0.085(3) 0.006(2) -0.011(3) -0.003(2)

_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 C2 1.725(3) . ?
S1 S1 2.0964(18) 3_556 ?
N1 C2 1.361(4) . ?
N1 C5 1.376(4) . ?
N2 C12 1.166(4) . ?
C2 C3 1.383(4) . ?
C3 C4 1.404(4) . ?
C3 C12 1.423(4) . ?
C4 C5 1.377(4) . ?
C4 C11 1.490(4) . ?
C5 C6 1.482(4) . ?
C6 C7 1.501(5) . ?
C7 C8 1.506(6) . ?
C8 C9 1.452(5) . ?
C9 C10 1.523(5) . ?
C10 C11 1.498(5) . ?

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
C2 S1 S1 103.76(11) . 3_556 ?
C2 N1 C5 110.3(3) . . ?
N1 C2 C3 106.6(3) . . ?
N1 C2 S1 126.1(3) . . ?
C3 C2 S1 127.2(3) . . ?
C2 C3 C4 108.7(3) . . ?
C2 C3 C12 123.7(3) . . ?
C4 C3 C12 127.6(3) . . ?
C5 C4 C3 106.8(3) . . ?
C5 C4 C11 125.4(3) . . ?
C3 C4 C11 127.8(3) . . ?
C4 C5 N1 107.6(3) . . ?
C4 C5 C6 130.1(3) . . ?
N1 C5 C6 122.3(3) . . ?
C5 C6 C7 116.0(3) . . ?
C6 C7 C8 117.3(3) . . ?
C9 C8 C7 119.2(4) . . ?
C8 C9 C10 118.4(4) . . ?
C11 C10 C9 116.4(3) . . ?
C4 C11 C10 115.0(3) . . ?
N2 C12 C3 178.8(4) . . ?

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        72.73
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.234
_refine_diff_density_min         -0.145
_refine_diff_density_rms         0.036
