# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2016

####################################################################### 
# 
# 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_I
_database_code_depnum_ccdc_archive 'CCDC 1001792'
_audit_update_record             
;
2016-02-02 deposited with the CCDC.
2016-03-09 downloaded from the CCDC.
;
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C20 H24 N2'
_chemical_formula_iupac          ?
_chemical_formula_weight         292.41

_chemical_melting_point          ?

_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   13.1094(7)
_cell_length_b                   8.9430(5)
_cell_length_c                   14.6031(9)
_cell_angle_alpha                90
_cell_angle_beta                 105.214(2)
_cell_angle_gamma                90
_cell_volume                     1652.03(16)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    5471
_cell_measurement_theta_min      2.6975
_cell_measurement_theta_max      28.2625
_cell_measurement_temperature    103.(2)

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.420
_exptl_crystal_size_mid          0.400
_exptl_crystal_size_min          0.160
_exptl_crystal_density_diffrn    1.176
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             632

_exptl_absorpt_coefficient_mu    0.069
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2012/1 (Bruker AXS Inc.)'
_exptl_absorpt_correction_T_min  0.86
_exptl_absorpt_correction_T_max  0.99

_exptl_special_details           
;
;

_diffrn_ambient_temperature      103.(2)

_diffrn_source                   'fine-focus sealed tube'
_diffrn_source_type              ?

_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  graphite

_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'

_diffrn_detector_area_resol_mean 8.3333

_diffrn_reflns_number            15157
_diffrn_reflns_av_R_equivalents  0.0279
_diffrn_reflns_av_unetI/netI     0.0272
_diffrn_reflns_theta_min         2.79
_diffrn_reflns_theta_max         28.30
_diffrn_reflns_theta_full        28.30
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19

_refine_special_details          
;
;

_reflns_number_total             4105
_reflns_number_gt                3394
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0530
_refine_ls_R_factor_gt           0.0421
_refine_ls_wR_factor_gt          0.1089
_refine_ls_wR_factor_ref         0.1168
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_restrained_S_all      1.027
_refine_ls_number_reflns         4105
_refine_ls_number_parameters     202
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment    constr
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0641P)²+0.4461P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?

_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.327
_refine_diff_density_min         -0.240
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

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'

_computing_data_collection       'APEX2 (Bruker AXS Inc., 2013)'
_computing_cell_refinement       'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_data_reduction        'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'XP (Bruker AXS Inc., 2013)'
_computing_publication_material  'APEX2 (Bruker AXS Inc., 2013)'

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C C1 0.14474(8) 0.57735(11) 0.29111(8) 0.0134(2) Uani d . . . 1 . .
C C2 0.04467(9) 0.63430(12) 0.29058(8) 0.0162(2) Uani d . . . 1 . .
H H2 -0.0038 0.6604 0.2321 0.019 Uiso calc U . R 1 . .
C C3 0.01613(10) 0.65262(13) 0.37503(9) 0.0221(3) Uani d . . . 1 . .
H H3 -0.0514 0.6927 0.3737 0.026 Uiso calc U . R 1 . .
C C4 0.08466(10) 0.61328(14) 0.46126(9) 0.0247(3) Uani d . . . 1 . .
H H4 0.0651 0.6275 0.5188 0.03 Uiso calc U . R 1 . .
C C5 0.18205(10) 0.55294(13) 0.46202(8) 0.0226(3) Uani d . . . 1 . .
H H5 0.2288 0.5234 0.5206 0.027 Uiso calc U . R 1 . .
C C6 0.21284(9) 0.53472(12) 0.37824(8) 0.0173(2) Uani d . . . 1 . .
H H6 0.2801 0.4933 0.3802 0.021 Uiso calc U . R 1 . .
C C7 0.13805(8) 0.64776(12) 0.05093(8) 0.0157(2) Uani d . . . 1 . .
C C8 0.06894(10) 0.74681(16) -0.02359(9) 0.0274(3) Uani d . . . 1 . .
H H8A 0.0235 0.6847 -0.0731 0.041 Uiso calc U . R 1 . .
H H8B 0.1135 0.8105 -0.0517 0.041 Uiso calc U . R 1 . .
H H8C 0.0249 0.8096 0.0057 0.041 Uiso calc U . R 1 . .
C C9 0.22151(8) 0.55212(12) 0.02344(8) 0.0150(2) Uani d . . . 1 . .
C C10 0.30259(9) 0.64983(13) -0.00893(8) 0.0201(2) Uani d . . . 1 . .
H H10A 0.2665 0.707 -0.0654 0.03 Uiso calc U . R 1 . .
H H10B 0.3565 0.5856 -0.0241 0.03 Uiso calc U . R 1 . .
H H10C 0.3363 0.7189 0.0421 0.03 Uiso calc U . R 1 . .
C C11 0.16681(10) 0.45132(14) -0.06084(9) 0.0238(3) Uani d . . . 1 . .
H H11A 0.109 0.3962 -0.0452 0.036 Uiso calc U . R 1 . .
H H11B 0.2182 0.3804 -0.0738 0.036 Uiso calc U . R 1 . .
H H11C 0.1384 0.5133 -0.1171 0.036 Uiso calc U . R 1 . .
C C12 0.27579(8) 0.45131(11) 0.10727(8) 0.0145(2) Uani d . . . 1 . .
H H12A 0.2375 0.3548 0.101 0.017 Uiso calc U . R 1 . .
H H12B 0.3487 0.4303 0.1036 0.017 Uiso calc U . R 1 . .
C C13 0.28062(8) 0.51743(11) 0.20463(7) 0.0126(2) Uani d . . . 1 . .
H H13 0.3044 0.4365 0.2528 0.015 Uiso calc U . R 1 . .
C C14 0.35566(8) 0.65195(11) 0.23500(8) 0.0132(2) Uani d . . . 1 . .
H H14A 0.3318 0.7341 0.1889 0.016 Uiso calc U . R 1 . .
H H14B 0.3499 0.6876 0.2976 0.016 Uiso calc U . R 1 . .
C C15 0.47042(8) 0.61942(11) 0.24171(7) 0.0134(2) Uani d . . . 1 . .
C C16 0.51887(9) 0.49006(12) 0.28608(8) 0.0165(2) Uani d . . . 1 . .
H H16 0.479 0.4205 0.3117 0.02 Uiso calc U . R 1 . .
C C17 0.62511(9) 0.46202(13) 0.29320(9) 0.0203(2) Uani d . . . 1 . .
H H17 0.6569 0.3728 0.3228 0.024 Uiso calc U . R 1 . .
C C18 0.68474(9) 0.56335(14) 0.25739(9) 0.0233(3) Uani d . . . 1 . .
H H18 0.7573 0.5442 0.2626 0.028 Uiso calc U . R 1 . .
C C19 0.63757(9) 0.69271(14) 0.21405(9) 0.0239(3) Uani d . . . 1 . .
H H19 0.6781 0.7629 0.1897 0.029 Uiso calc U . R 1 . .
C C20 0.53106(9) 0.72056(13) 0.20592(8) 0.0186(2) Uani d . . . 1 . .
H H20 0.4994 0.8094 0.1757 0.022 Uiso calc U . R 1 . .
N N1 0.17288(7) 0.55925(10) 0.20525(6) 0.01294(19) Uani d . . . 1 . .
N N2 0.11562(7) 0.64881(10) 0.13168(7) 0.0146(2) Uani d . . . 1 . .


_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_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
C1 C6 . 1.4017(16) ?
C1 C2 . 1.4054(15) ?
C1 N1 . 1.4062(13) ?
C2 C3 . 1.3893(15) ?
C2 H2 . 0.95 ?
C3 C4 . 1.3867(19) ?
C3 H3 . 0.95 ?
C4 C5 . 1.3834(18) ?
C4 H4 . 0.95 ?
C5 C6 . 1.3948(16) ?
C5 H5 . 0.95 ?
C6 H6 . 0.95 ?
C7 N2 . 1.2881(14) ?
C7 C8 . 1.5073(15) ?
C7 C9 . 1.5233(15) ?
C8 H8A . 0.98 ?
C8 H8B . 0.98 ?
C8 H8C . 0.98 ?
C9 C12 . 1.5364(15) ?
C9 C11 . 1.5422(15) ?
C9 C10 . 1.5429(15) ?
C10 H10A . 0.98 ?
C10 H10B . 0.98 ?
C10 H10C . 0.98 ?
C11 H11A . 0.98 ?
C11 H11B . 0.98 ?
C11 H11C . 0.98 ?
C12 C13 . 1.5258(14) ?
C12 H12A . 0.99 ?
C12 H12B . 0.99 ?
C13 N1 . 1.4634(12) ?
C13 C14 . 1.5436(14) ?
C13 H13 . 1.0 ?
C14 C15 . 1.5100(14) ?
C14 H14A . 0.99 ?
C14 H14B . 0.99 ?
C15 C20 . 1.3932(15) ?
C15 C16 . 1.3949(15) ?
C16 C17 . 1.3919(15) ?
C16 H16 . 0.95 ?
C17 C18 . 1.3858(17) ?
C17 H17 . 0.95 ?
C18 C19 . 1.3842(18) ?
C18 H18 . 0.95 ?
C19 C20 . 1.3924(16) ?
C19 H19 . 0.95 ?
C20 H20 . 0.95 ?
N1 N2 . 1.3913(12) ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C6 C1 C2 . . 118.35(10) ?
C6 C1 N1 . . 121.63(10) ?
C2 C1 N1 . . 119.98(10) ?
C3 C2 C1 . . 120.41(11) ?
C3 C2 H2 . . 119.8 ?
C1 C2 H2 . . 119.8 ?
C4 C3 C2 . . 121.00(11) ?
C4 C3 H3 . . 119.5 ?
C2 C3 H3 . . 119.5 ?
C5 C4 C3 . . 118.87(11) ?
C5 C4 H4 . . 120.6 ?
C3 C4 H4 . . 120.6 ?
C4 C5 C6 . . 121.16(11) ?
C4 C5 H5 . . 119.4 ?
C6 C5 H5 . . 119.4 ?
C5 C6 C1 . . 120.16(11) ?
C5 C6 H6 . . 119.9 ?
C1 C6 H6 . . 119.9 ?
N2 C7 C8 . . 114.73(10) ?
N2 C7 C9 . . 126.70(10) ?
C8 C7 C9 . . 118.49(9) ?
C7 C8 H8A . . 109.5 ?
C7 C8 H8B . . 109.5 ?
H8A C8 H8B . . 109.5 ?
C7 C8 H8C . . 109.5 ?
H8A C8 H8C . . 109.5 ?
H8B C8 H8C . . 109.5 ?
C7 C9 C12 . . 109.51(8) ?
C7 C9 C11 . . 108.84(9) ?
C12 C9 C11 . . 108.30(9) ?
C7 C9 C10 . . 111.28(9) ?
C12 C9 C10 . . 111.35(9) ?
C11 C9 C10 . . 107.45(9) ?
C9 C10 H10A . . 109.5 ?
C9 C10 H10B . . 109.5 ?
H10A C10 H10B . . 109.5 ?
C9 C10 H10C . . 109.5 ?
H10A C10 H10C . . 109.5 ?
H10B C10 H10C . . 109.5 ?
C9 C11 H11A . . 109.5 ?
C9 C11 H11B . . 109.5 ?
H11A C11 H11B . . 109.5 ?
C9 C11 H11C . . 109.5 ?
H11A C11 H11C . . 109.5 ?
H11B C11 H11C . . 109.5 ?
C13 C12 C9 . . 114.36(8) ?
C13 C12 H12A . . 108.7 ?
C9 C12 H12A . . 108.7 ?
C13 C12 H12B . . 108.7 ?
C9 C12 H12B . . 108.7 ?
H12A C12 H12B . . 107.6 ?
N1 C13 C12 . . 107.50(8) ?
N1 C13 C14 . . 110.02(8) ?
C12 C13 C14 . . 115.93(8) ?
N1 C13 H13 . . 107.7 ?
C12 C13 H13 . . 107.7 ?
C14 C13 H13 . . 107.7 ?
C15 C14 C13 . . 114.67(8) ?
C15 C14 H14A . . 108.6 ?
C13 C14 H14A . . 108.6 ?
C15 C14 H14B . . 108.6 ?
C13 C14 H14B . . 108.6 ?
H14A C14 H14B . . 107.6 ?
C20 C15 C16 . . 118.53(10) ?
C20 C15 C14 . . 120.49(9) ?
C16 C15 C14 . . 120.95(9) ?
C17 C16 C15 . . 120.59(10) ?
C17 C16 H16 . . 119.7 ?
C15 C16 H16 . . 119.7 ?
C18 C17 C16 . . 120.43(11) ?
C18 C17 H17 . . 119.8 ?
C16 C17 H17 . . 119.8 ?
C19 C18 C17 . . 119.37(11) ?
C19 C18 H18 . . 120.3 ?
C17 C18 H18 . . 120.3 ?
C18 C19 C20 . . 120.41(11) ?
C18 C19 H19 . . 119.8 ?
C20 C19 H19 . . 119.8 ?
C19 C20 C15 . . 120.66(11) ?
C19 C20 H20 . . 119.7 ?
C15 C20 H20 . . 119.7 ?
N2 N1 C1 . . 114.06(8) ?
N2 N1 C13 . . 117.93(8) ?
C1 N1 C13 . . 120.95(9) ?
C7 N2 N1 . . 119.75(9) ?


####################################################################### 
# 
# 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_I
_database_code_depnum_ccdc_archive 'CCDC 1001827'
_audit_update_record             
;
2016-02-02 deposited with the CCDC.
2016-03-09 downloaded from the CCDC.
;
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C23 H24 N2 S'
_chemical_formula_iupac          ?
_chemical_formula_weight         360.50

_chemical_melting_point          ?

_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   11.6939(7)
_cell_length_b                   9.4598(5)
_cell_length_c                   16.9069(10)
_cell_angle_alpha                90
_cell_angle_beta                 91.481(3)
_cell_angle_gamma                90
_cell_volume                     1869.65(19)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4566
_cell_measurement_theta_min      2.4101
_cell_measurement_theta_max      30.6525
_cell_measurement_temperature    103.(2)

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.420
_exptl_crystal_size_mid          0.340
_exptl_crystal_size_min          0.320
_exptl_crystal_density_diffrn    1.281
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             768

_exptl_absorpt_coefficient_mu    0.182
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2012/1 (Bruker AXS Inc.)'
_exptl_absorpt_correction_T_min  0.87
_exptl_absorpt_correction_T_max  0.94

_exptl_special_details           
;
;

_diffrn_ambient_temperature      103.(2)

_diffrn_source                   ?
_diffrn_source_type              ?

_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073

_diffrn_radiation_monochromator  graphite

_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'

_diffrn_detector_area_resol_mean 8.3333

_diffrn_reflns_number            43539
_diffrn_reflns_av_R_equivalents  0.0764
_diffrn_reflns_av_sigmaI/netI    0.0614
_diffrn_reflns_theta_min         2.41
_diffrn_reflns_theta_max         35.10
_diffrn_reflns_theta_full        35.10
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_limit_l_max       27

_refine_special_details          
;
;

_reflns_number_total             8277
_reflns_number_gt                5674
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0851
_refine_ls_R_factor_gt           0.0497
_refine_ls_wR_factor_gt          0.1172
_refine_ls_wR_factor_ref         0.1342
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_restrained_S_all      1.042
_refine_ls_number_reflns         8277
_refine_ls_number_parameters     237
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment    constr
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0607P)²+0.2604P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?

_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.609
_refine_diff_density_min         -0.324
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

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'

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_data_reduction        'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C C1 -0.11532(12) 1.05986(14) 0.09091(8) 0.0210(3) Uani d . . . 1 . .
H H1 -0.1443 1.1006 0.0431 0.025 Uiso calc U . R 1 . .
C C2 -0.17897(11) 1.03700(14) 0.15568(8) 0.0202(2) Uani d . . . 1 . .
H H2 -0.2579 1.0599 0.1583 0.024 Uiso calc U . R 1 . .
C C3 -0.11456(11) 0.97491(13) 0.21918(8) 0.0169(2) Uani d . . . 1 . .
H H3 -0.1461 0.9521 0.2688 0.02 Uiso calc U . R 1 . .
C C4 -0.00220(10) 0.95122(12) 0.20148(7) 0.0134(2) Uani d . . . 1 . .
C C5 0.09323(10) 0.88976(12) 0.24811(7) 0.0124(2) Uani d . . . 1 . .
C C6 0.07464(10) 0.82451(12) 0.32911(7) 0.0134(2) Uani d . . . 1 . .
C C7 -0.01624(11) 0.70698(13) 0.32154(8) 0.0184(2) Uani d . . . 1 . .
H H7A -0.0908 0.7491 0.3083 0.028 Uiso calc U . R 1 . .
H H7B -0.0205 0.6561 0.3718 0.028 Uiso calc U . R 1 . .
H H7C 0.0049 0.641 0.2797 0.028 Uiso calc U . R 1 . .
C C8 0.03661(11) 0.93584(14) 0.38968(7) 0.0177(2) Uani d . . . 1 . .
H H8A 0.0918 1.0138 0.3915 0.027 Uiso calc U . R 1 . .
H H8B 0.0329 0.8922 0.4421 0.027 Uiso calc U . R 1 . .
H H8C -0.0391 0.9722 0.3739 0.027 Uiso calc U . R 1 . .
C C9 0.18660(10) 0.75192(13) 0.35685(7) 0.0144(2) Uani d . . . 1 . .
H H9A 0.1881 0.7468 0.4154 0.017 Uiso calc U . R 1 . .
H H9B 0.1865 0.6538 0.3365 0.017 Uiso calc U . R 1 . .
C C10 0.29547(10) 0.82486(12) 0.33078(7) 0.0138(2) Uani d . . . 1 . .
H H10 0.3608 0.7596 0.343 0.017 Uiso calc U . R 1 . .
C C11 0.32430(11) 0.96873(13) 0.36929(7) 0.0156(2) Uani d . . . 1 . .
H H11A 0.3984 1.0019 0.3493 0.019 Uiso calc U . R 1 . .
H H11B 0.2652 1.0381 0.3524 0.019 Uiso calc U . R 1 . .
C C12 0.33159(10) 0.96644(13) 0.45858(7) 0.0142(2) Uani d . . . 1 . .
C C13 0.38736(12) 0.85802(14) 0.49979(8) 0.0210(3) Uani d . . . 1 . .
H H13 0.4216 0.7833 0.4713 0.025 Uiso calc U . R 1 . .
C C14 0.39376(13) 0.85742(14) 0.58203(8) 0.0228(3) Uani d . . . 1 . .
H H14 0.431 0.7817 0.6092 0.027 Uiso calc U . R 1 . .
C C15 0.34612(11) 0.96679(14) 0.62455(8) 0.0189(2) Uani d . . . 1 . .
H H15 0.3507 0.9667 0.6807 0.023 Uiso calc U . R 1 . .
C C16 0.29183(11) 1.07610(14) 0.58447(8) 0.0202(2) Uani d . . . 1 . .
H H16 0.2598 1.1521 0.6132 0.024 Uiso calc U . R 1 . .
C C17 0.28398(11) 1.07513(13) 0.50223(8) 0.0187(2) Uani d . . . 1 . .
H H17 0.2454 1.1501 0.4754 0.022 Uiso calc U . R 1 . .
C C18 0.38255(10) 0.83740(12) 0.19638(7) 0.0140(2) Uani d . . . 1 . .
C C19 0.49162(11) 0.80630(13) 0.22740(8) 0.0172(2) Uani d . . . 1 . .
H H19 0.5025 0.7903 0.2825 0.021 Uiso calc U . R 1 . .
C C20 0.58407(11) 0.79882(14) 0.17762(8) 0.0205(3) Uani d . . . 1 . .
H H20 0.6578 0.7774 0.1993 0.025 Uiso calc U . R 1 . .
C C21 0.57091(12) 0.82196(15) 0.09703(8) 0.0237(3) Uani d . . . 1 . .
H H21 0.6346 0.8158 0.0634 0.028 Uiso calc U . R 1 . .
C C22 0.46299(12) 0.85426(14) 0.06647(8) 0.0212(3) Uani d . . . 1 . .
H H22 0.453 0.8714 0.0114 0.025 Uiso calc U . R 1 . .
C C23 0.36945(11) 0.86200(13) 0.11490(7) 0.0165(2) Uani d . . . 1 . .
H H23 0.2961 0.8841 0.0928 0.02 Uiso calc U . R 1 . .
N N1 0.18875(8) 0.89099(11) 0.21066(6) 0.01335(18) Uani d . . . 1 . .
N N2 0.28691(9) 0.84035(11) 0.24483(6) 0.01521(19) Uani d . . . 1 . .
S S1 0.02368(3) 1.00632(3) 0.10585(2) 0.01655(8) Uani d . . . 1 . .


_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_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
C1 C2 . 1.3572(19) ?
C1 S1 . 1.7150(14) ?
C1 H1 . 0.95 ?
C2 C3 . 1.4224(18) ?
C2 H2 . 0.95 ?
C3 C4 . 1.3734(17) ?
C3 H3 . 0.95 ?
C4 C5 . 1.4695(17) ?
C4 S1 . 1.7329(12) ?
C5 N1 . 1.2982(14) ?
C5 C6 . 1.5228(16) ?
C6 C9 . 1.5408(17) ?
C6 C7 . 1.5411(17) ?
C6 C8 . 1.5425(17) ?
C7 H7A . 0.98 ?
C7 H7B . 0.98 ?
C7 H7C . 0.98 ?
C8 H8A . 0.98 ?
C8 H8B . 0.98 ?
C8 H8C . 0.98 ?
C9 C10 . 1.5231(17) ?
C9 H9A . 0.99 ?
C9 H9B . 0.99 ?
C10 N2 . 1.4613(15) ?
C10 C11 . 1.5422(17) ?
C10 H10 . 1.0 ?
C11 C12 . 1.5101(17) ?
C11 H11A . 0.99 ?
C11 H11B . 0.99 ?
C12 C17 . 1.3903(17) ?
C12 C13 . 1.3925(17) ?
C13 C14 . 1.3906(18) ?
C13 H13 . 0.95 ?
C14 C15 . 1.3849(18) ?
C14 H14 . 0.95 ?
C15 C16 . 1.3818(19) ?
C15 H15 . 0.95 ?
C16 C17 . 1.3910(18) ?
C16 H16 . 0.95 ?
C17 H17 . 0.95 ?
C18 C19 . 1.3979(17) ?
C18 C23 . 1.4016(17) ?
C18 N2 . 1.4036(15) ?
C19 C20 . 1.3890(17) ?
C19 H19 . 0.95 ?
C20 C21 . 1.385(2) ?
C20 H20 . 0.95 ?
C21 C22 . 1.385(2) ?
C21 H21 . 0.95 ?
C22 C23 . 1.3851(17) ?
C22 H22 . 0.95 ?
C23 H23 . 0.95 ?
N1 N2 . 1.3589(14) ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C2 C1 S1 . . 111.82(10) ?
C2 C1 H1 . . 124.1 ?
S1 C1 H1 . . 124.1 ?
C1 C2 C3 . . 112.58(12) ?
C1 C2 H2 . . 123.7 ?
C3 C2 H2 . . 123.7 ?
C4 C3 C2 . . 113.19(11) ?
C4 C3 H3 . . 123.4 ?
C2 C3 H3 . . 123.4 ?
C3 C4 C5 . . 131.70(11) ?
C3 C4 S1 . . 110.21(9) ?
C5 C4 S1 . . 118.10(8) ?
N1 C5 C4 . . 112.70(10) ?
N1 C5 C6 . . 125.93(10) ?
C4 C5 C6 . . 121.25(10) ?
C5 C6 C9 . . 108.33(9) ?
C5 C6 C7 . . 109.38(10) ?
C9 C6 C7 . . 106.41(9) ?
C5 C6 C8 . . 111.75(10) ?
C9 C6 C8 . . 111.07(10) ?
C7 C6 C8 . . 109.73(10) ?
C6 C7 H7A . . 109.5 ?
C6 C7 H7B . . 109.5 ?
H7A C7 H7B . . 109.5 ?
C6 C7 H7C . . 109.5 ?
H7A C7 H7C . . 109.5 ?
H7B C7 H7C . . 109.5 ?
C6 C8 H8A . . 109.5 ?
C6 C8 H8B . . 109.5 ?
H8A C8 H8B . . 109.5 ?
C6 C8 H8C . . 109.5 ?
H8A C8 H8C . . 109.5 ?
H8B C8 H8C . . 109.5 ?
C10 C9 C6 . . 114.84(10) ?
C10 C9 H9A . . 108.6 ?
C6 C9 H9A . . 108.6 ?
C10 C9 H9B . . 108.6 ?
C6 C9 H9B . . 108.6 ?
H9A C9 H9B . . 107.5 ?
N2 C10 C9 . . 107.27(10) ?
N2 C10 C11 . . 109.87(9) ?
C9 C10 C11 . . 116.92(10) ?
N2 C10 H10 . . 107.5 ?
C9 C10 H10 . . 107.5 ?
C11 C10 H10 . . 107.5 ?
C12 C11 C10 . . 114.55(10) ?
C12 C11 H11A . . 108.6 ?
C10 C11 H11A . . 108.6 ?
C12 C11 H11B . . 108.6 ?
C10 C11 H11B . . 108.6 ?
H11A C11 H11B . . 107.6 ?
C17 C12 C13 . . 117.90(11) ?
C17 C12 C11 . . 120.47(11) ?
C13 C12 C11 . . 121.62(11) ?
C14 C13 C12 . . 121.04(12) ?
C14 C13 H13 . . 119.5 ?
C12 C13 H13 . . 119.5 ?
C15 C14 C13 . . 120.26(12) ?
C15 C14 H14 . . 119.9 ?
C13 C14 H14 . . 119.9 ?
C16 C15 C14 . . 119.37(12) ?
C16 C15 H15 . . 120.3 ?
C14 C15 H15 . . 120.3 ?
C15 C16 C17 . . 120.19(12) ?
C15 C16 H16 . . 119.9 ?
C17 C16 H16 . . 119.9 ?
C12 C17 C16 . . 121.22(12) ?
C12 C17 H17 . . 119.4 ?
C16 C17 H17 . . 119.4 ?
C19 C18 C23 . . 118.64(11) ?
C19 C18 N2 . . 121.21(11) ?
C23 C18 N2 . . 120.13(11) ?
C20 C19 C18 . . 120.02(12) ?
C20 C19 H19 . . 120.0 ?
C18 C19 H19 . . 120.0 ?
C21 C20 C19 . . 121.32(13) ?
C21 C20 H20 . . 119.3 ?
C19 C20 H20 . . 119.3 ?
C20 C21 C22 . . 118.61(12) ?
C20 C21 H21 . . 120.7 ?
C22 C21 H21 . . 120.7 ?
C23 C22 C21 . . 121.13(12) ?
C23 C22 H22 . . 119.4 ?
C21 C22 H22 . . 119.4 ?
C22 C23 C18 . . 120.28(12) ?
C22 C23 H23 . . 119.9 ?
C18 C23 H23 . . 119.9 ?
C5 N1 N2 . . 121.17(10) ?
N1 N2 C18 . . 115.84(10) ?
N1 N2 C10 . . 119.57(9) ?
C18 N2 C10 . . 122.91(10) ?
C1 S1 C4 . . 92.20(6) ?


