# Electronic Supplementary Material (ESI) for ChemComm.
# 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_xx0511
_database_code_depnum_ccdc_archive 'CCDC 1414046'
_audit_update_record             
;
2015-07-21 deposited with the CCDC.
2015-12-24 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
Trans-2,3-di-4-tolyl-4-tosyl-1,2,3,4-tetrahydrocyclopenta[b]indole
_chemical_name_common            6t
_chemical_melting_point          ?
_chemical_formula_moiety         'C32 H29 N O2 S'
_chemical_formula_sum            'C32 H29 N O2 S'
_chemical_formula_weight         491.62

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   P2(1)/c

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

_cell_length_a                   11.6200(16)
_cell_length_b                   11.0673(14)
_cell_length_c                   21.125(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 98.311(4)
_cell_angle_gamma                90.00
_cell_volume                     2688.2(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    2699
_cell_measurement_theta_min      2.44
_cell_measurement_theta_max      20.91

_exptl_crystal_description       BLOCK
_exptl_crystal_colour            COLORLESS
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.15
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.215
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1040
_exptl_absorpt_coefficient_mu    0.149
_exptl_absorpt_correction_type   MULTI-SCAN
_exptl_absorpt_correction_T_min  0.9708
_exptl_absorpt_correction_T_max  0.9780
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            14617
_diffrn_reflns_av_R_equivalents  0.0533
_diffrn_reflns_av_sigmaI/netI    0.0583
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         1.77
_diffrn_reflns_theta_max         25.00
_reflns_number_total             4714
_reflns_number_gt                2663
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.0613P)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    CONSTR
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         4714
_refine_ls_number_parameters     328
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0965
_refine_ls_R_factor_gt           0.0481
_refine_ls_wR_factor_ref         0.1345
_refine_ls_wR_factor_gt          0.1195
_refine_ls_goodness_of_fit_ref   1.002
_refine_ls_restrained_S_all      1.003
_refine_ls_shift/su_max          0.014
_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 0.47469(5) 0.61154(7) 0.16253(3) 0.0714(2) Uani 1 1 d U . .
O2 O 0.48164(15) 0.70469(16) 0.11603(9) 0.0851(5) Uani 1 1 d U . .
C26 C 0.1174(2) 0.9744(2) 0.12847(11) 0.0544(6) Uani 1 1 d . . .
N1 N 0.35306(16) 0.64004(18) 0.19324(9) 0.0659(6) Uani 1 1 d . . .
C13 C 0.2061(2) 0.6186(2) 0.25328(13) 0.0659(7) Uani 1 1 d . . .
C8 C 0.2555(2) 0.7066(2) 0.16447(12) 0.0598(6) Uani 1 1 d . . .
C6 C 0.45214(19) 0.4721(2) 0.12395(12) 0.0588(6) Uani 1 1 d . . .
O1 O 0.56313(14) 0.5975(2) 0.21577(9) 0.1013(7) Uani 1 1 d . . .
C12 C 0.1697(2) 0.6967(2) 0.20005(13) 0.0648(7) Uani 1 1 d . . .
C18 C 0.3201(2) 0.5832(2) 0.24824(12) 0.0678(7) Uani 1 1 d . . .
C19 C 0.2213(2) 0.7178(2) 0.04325(12) 0.0623(6) Uani 1 1 d . . .
C20 C 0.1564(2) 0.6141(2) 0.03218(12) 0.0649(7) Uani 1 1 d . . .
H20 H 0.1175 0.5839 0.0643 0.078 Uiso 1 1 calc R . .
C31 C 0.1871(2) 1.0239(2) 0.18052(12) 0.0671(7) Uani 1 1 d . . .
H31 H 0.2311 0.9730 0.2095 0.081 Uiso 1 1 calc R . .
C5 C 0.4134(2) 0.4673(2) 0.06000(12) 0.0630(6) Uani 1 1 d . . .
H5 H 0.4016 0.5382 0.0363 0.076 Uiso 1 1 calc R . .
C29 C 0.1305(2) 1.2256(2) 0.14803(13) 0.0653(7) Uani 1 1 d . . .
C27 C 0.0548(2) 1.0542(2) 0.08661(11) 0.0681(7) Uani 1 1 d . . .
H27 H 0.0063 1.0243 0.0512 0.082 Uiso 1 1 calc R . .
C28 C 0.0628(2) 1.1774(2) 0.09633(13) 0.0729(7) Uani 1 1 d . . .
H28 H 0.0208 1.2288 0.0667 0.087 Uiso 1 1 calc R . .
C9 C 0.2302(2) 0.7836(2) 0.10622(12) 0.0648(7) Uani 1 1 d . . .
H9 H 0.2886 0.8477 0.1076 0.078 Uiso 1 1 calc R . .
C10 C 0.1086(2) 0.8402(2) 0.11718(13) 0.0677(7) Uani 1 1 d . . .
H10 H 0.0522 0.8255 0.0788 0.081 Uiso 1 1 calc R . .
C21 C 0.1477(2) 0.5539(3) -0.02530(13) 0.0784(8) Uani 1 1 d . . .
H21 H 0.1046 0.4829 -0.0307 0.094 Uiso 1 1 calc R . .
C24 C 0.2754(3) 0.7608(3) -0.00642(15) 0.0832(8) Uani 1 1 d . . .
H24 H 0.3197 0.8310 -0.0008 0.100 Uiso 1 1 calc R . .
C4 C 0.3917(2) 0.3565(3) 0.03041(13) 0.0733(7) Uani 1 1 d . . .
H4 H 0.3666 0.3539 -0.0134 0.088 Uiso 1 1 calc R . .
C17 C 0.3805(3) 0.5038(3) 0.29162(14) 0.0877(9) Uani 1 1 d . . .
H17 H 0.4563 0.4807 0.2880 0.105 Uiso 1 1 calc R . .
C30 C 0.1928(2) 1.1466(2) 0.19040(12) 0.0698(7) Uani 1 1 d . . .
H30 H 0.2395 1.1769 0.2263 0.084 Uiso 1 1 calc R . .
C14 C 0.1522(3) 0.5740(2) 0.30347(15) 0.0836(9) Uani 1 1 d . . .
H14 H 0.0770 0.5977 0.3080 0.100 Uiso 1 1 calc R . .
C23 C 0.2643(3) 0.7002(3) -0.06443(16) 0.0982(10) Uani 1 1 d . . .
H23 H 0.3010 0.7315 -0.0971 0.118 Uiso 1 1 calc R . .
C1 C 0.4710(3) 0.3662(3) 0.15872(14) 0.0861(9) Uani 1 1 d . . .
H1 H 0.4995 0.3687 0.2022 0.103 Uiso 1 1 calc R . .
C3 C 0.4065(3) 0.2498(3) 0.06420(16) 0.0813(8) Uani 1 1 d . . .
C11 C 0.0672(2) 0.7712(2) 0.17466(15) 0.0860(9) Uani 1 1 d . . .
H11A H 0.0475 0.8271 0.2068 0.103 Uiso 1 1 calc R . .
H11B H 0.0002 0.7208 0.1603 0.103 Uiso 1 1 calc R . .
C2 C 0.4470(3) 0.2566(3) 0.12817(16) 0.0965(10) Uani 1 1 d . . .
H2 H 0.4588 0.1857 0.1518 0.116 Uiso 1 1 calc R . .
C22 C 0.2014(3) 0.5964(3) -0.07520(14) 0.0874(9) Uani 1 1 d . . .
C7 C 0.3797(4) 0.1293(3) 0.03093(19) 0.1334(15) Uani 1 1 d . . .
H7A H 0.4359 0.0704 0.0487 0.200 Uiso 1 1 calc R . .
H7B H 0.3829 0.1382 -0.0140 0.200 Uiso 1 1 calc R . .
H7C H 0.3033 0.1032 0.0371 0.200 Uiso 1 1 calc R . .
C32 C 0.1386(3) 1.3595(2) 0.16006(18) 0.1082(11) Uani 1 1 d . . .
H32A H 0.2137 1.3880 0.1529 0.162 Uiso 1 1 calc R . .
H32B H 0.1280 1.3758 0.2035 0.162 Uiso 1 1 calc R . .
H32C H 0.0793 1.4001 0.1314 0.162 Uiso 1 1 calc R . .
C15 C 0.2126(3) 0.4942(3) 0.34604(15) 0.0995(10) Uani 1 1 d . . .
H15 H 0.1770 0.4629 0.3792 0.119 Uiso 1 1 calc R . .
C25 C 0.1937(3) 0.5311(4) -0.13813(15) 0.1478(17) Uani 1 1 d . . .
H25A H 0.2435 0.5699 -0.1644 0.222 Uiso 1 1 calc R . .
H25B H 0.1149 0.5331 -0.1594 0.222 Uiso 1 1 calc R . .
H25C H 0.2177 0.4487 -0.1307 0.222 Uiso 1 1 calc R . .
C16 C 0.3251(3) 0.4598(3) 0.34043(14) 0.0994(10) Uani 1 1 d . . .
H16 H 0.3641 0.4063 0.3700 0.119 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
S1 O1 1.4181(19) . ?
S1 O2 1.4344(19) . ?
S1 N1 1.6682(19) . ?
S1 C6 1.748(2) . ?
C26 C27 1.379(3) . ?
C26 C31 1.381(3) . ?
C26 C10 1.506(3) . ?
N1 C8 1.413(3) . ?
N1 C18 1.422(3) . ?
C13 C14 1.398(3) . ?
C13 C18 1.400(3) . ?
C13 C12 1.433(3) . ?
C8 C12 1.337(3) . ?
C8 C9 1.490(3) . ?
C6 C5 1.362(3) . ?
C6 C1 1.384(3) . ?
C12 C11 1.484(4) . ?
C18 C17 1.386(4) . ?
C19 C20 1.374(3) . ?
C19 C24 1.383(3) . ?
C19 C9 1.507(3) . ?
C20 C21 1.376(3) . ?
C20 H20 0.9300 . ?
C31 C30 1.374(3) . ?
C31 H31 0.9300 . ?
C5 C4 1.383(3) . ?
C5 H5 0.9300 . ?
C29 C28 1.359(3) . ?
C29 C30 1.380(3) . ?
C29 C32 1.504(3) . ?
C27 C28 1.381(3) . ?
C27 H27 0.9300 . ?
C28 H28 0.9300 . ?
C9 C10 1.593(3) . ?
C9 H9 0.9800 . ?
C10 C11 1.568(4) . ?
C10 H10 0.9800 . ?
C21 C22 1.383(4) . ?
C21 H21 0.9300 . ?
C24 C23 1.386(4) . ?
C24 H24 0.9300 . ?
C4 C3 1.377(4) . ?
C4 H4 0.9300 . ?
C17 C16 1.381(4) . ?
C17 H17 0.9300 . ?
C30 H30 0.9300 . ?
C14 C15 1.378(4) . ?
C14 H14 0.9300 . ?
C23 C22 1.364(4) . ?
C23 H23 0.9300 . ?
C1 C2 1.383(4) . ?
C1 H1 0.9300 . ?
C3 C2 1.368(4) . ?
C3 C7 1.519(4) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C2 H2 0.9300 . ?
C22 C25 1.504(4) . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
C32 H32A 0.9600 . ?
C32 H32B 0.9600 . ?
C32 H32C 0.9600 . ?
C15 C16 1.383(4) . ?
C15 H15 0.9300 . ?
C25 H25A 0.9600 . ?
C25 H25B 0.9600 . ?
C25 H25C 0.9600 . ?
C16 H16 0.9300 . ?

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
O1 S1 O2 121.05(12) . . ?
O1 S1 N1 105.65(11) . . ?
O2 S1 N1 105.38(11) . . ?
O1 S1 C6 108.41(13) . . ?
O2 S1 C6 109.56(12) . . ?
N1 S1 C6 105.67(10) . . ?
C27 C26 C31 116.8(2) . . ?
C27 C26 C10 120.8(2) . . ?
C31 C26 C10 122.4(2) . . ?
C8 N1 C18 106.7(2) . . ?
C8 N1 S1 127.09(18) . . ?
C18 N1 S1 125.30(19) . . ?
C14 C13 C18 119.4(3) . . ?
C14 C13 C12 134.0(3) . . ?
C18 C13 C12 106.5(2) . . ?
C12 C8 N1 109.4(2) . . ?
C12 C8 C9 115.9(2) . . ?
N1 C8 C9 134.7(2) . . ?
C5 C6 C1 119.9(2) . . ?
C5 C6 S1 120.2(2) . . ?
C1 C6 S1 119.9(2) . . ?
C8 C12 C13 109.3(2) . . ?
C8 C12 C11 112.1(2) . . ?
C13 C12 C11 138.5(2) . . ?
C17 C18 C13 121.5(3) . . ?
C17 C18 N1 130.6(2) . . ?
C13 C18 N1 107.9(2) . . ?
C20 C19 C24 117.2(2) . . ?
C20 C19 C9 121.3(2) . . ?
C24 C19 C9 121.5(2) . . ?
C19 C20 C21 121.6(2) . . ?
C19 C20 H20 119.2 . . ?
C21 C20 H20 119.2 . . ?
C30 C31 C26 121.5(2) . . ?
C30 C31 H31 119.2 . . ?
C26 C31 H31 119.2 . . ?
C6 C5 C4 119.7(2) . . ?
C6 C5 H5 120.1 . . ?
C4 C5 H5 120.1 . . ?
C28 C29 C30 117.4(2) . . ?
C28 C29 C32 122.5(3) . . ?
C30 C29 C32 120.1(3) . . ?
C26 C27 C28 121.2(2) . . ?
C26 C27 H27 119.4 . . ?
C28 C27 H27 119.4 . . ?
C29 C28 C27 121.7(2) . . ?
C29 C28 H28 119.1 . . ?
C27 C28 H28 119.1 . . ?
C8 C9 C19 115.66(18) . . ?
C8 C9 C10 100.27(19) . . ?
C19 C9 C10 111.7(2) . . ?
C8 C9 H9 109.6 . . ?
C19 C9 H9 109.6 . . ?
C10 C9 H9 109.6 . . ?
C26 C10 C11 112.3(2) . . ?
C26 C10 C9 111.75(19) . . ?
C11 C10 C9 107.4(2) . . ?
C26 C10 H10 108.4 . . ?
C11 C10 H10 108.4 . . ?
C9 C10 H10 108.4 . . ?
C20 C21 C22 121.6(3) . . ?
C20 C21 H21 119.2 . . ?
C22 C21 H21 119.2 . . ?
C19 C24 C23 120.6(3) . . ?
C19 C24 H24 119.7 . . ?
C23 C24 H24 119.7 . . ?
C3 C4 C5 121.6(3) . . ?
C3 C4 H4 119.2 . . ?
C5 C4 H4 119.2 . . ?
C16 C17 C18 118.1(3) . . ?
C16 C17 H17 121.0 . . ?
C18 C17 H17 121.0 . . ?
C31 C30 C29 121.3(2) . . ?
C31 C30 H30 119.4 . . ?
C29 C30 H30 119.4 . . ?
C15 C14 C13 118.7(3) . . ?
C15 C14 H14 120.7 . . ?
C13 C14 H14 120.7 . . ?
C22 C23 C24 122.3(3) . . ?
C22 C23 H23 118.9 . . ?
C24 C23 H23 118.9 . . ?
C2 C1 C6 119.3(3) . . ?
C2 C1 H1 120.4 . . ?
C6 C1 H1 120.4 . . ?
C2 C3 C4 117.7(3) . . ?
C2 C3 C7 121.6(3) . . ?
C4 C3 C7 120.7(3) . . ?
C12 C11 C10 103.3(2) . . ?
C12 C11 H11A 111.1 . . ?
C10 C11 H11A 111.1 . . ?
C12 C11 H11B 111.1 . . ?
C10 C11 H11B 111.1 . . ?
H11A C11 H11B 109.1 . . ?
C3 C2 C1 121.8(3) . . ?
C3 C2 H2 119.1 . . ?
C1 C2 H2 119.1 . . ?
C23 C22 C21 116.7(3) . . ?
C23 C22 C25 120.9(3) . . ?
C21 C22 C25 122.3(4) . . ?
C3 C7 H7A 109.5 . . ?
C3 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C3 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C29 C32 H32A 109.5 . . ?
C29 C32 H32B 109.5 . . ?
H32A C32 H32B 109.5 . . ?
C29 C32 H32C 109.5 . . ?
H32A C32 H32C 109.5 . . ?
H32B C32 H32C 109.5 . . ?
C14 C15 C16 121.3(3) . . ?
C14 C15 H15 119.4 . . ?
C16 C15 H15 119.4 . . ?
C22 C25 H25A 109.5 . . ?
C22 C25 H25B 109.5 . . ?
H25A C25 H25B 109.5 . . ?
C22 C25 H25C 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
C17 C16 C15 121.1(3) . . ?
C17 C16 H16 119.5 . . ?
C15 C16 H16 119.5 . . ?

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
O1 S1 N1 C8 152.22(19) . . . . ?
O2 S1 N1 C8 23.0(2) . . . . ?
C6 S1 N1 C8 -93.0(2) . . . . ?
O1 S1 N1 C18 -39.9(2) . . . . ?
O2 S1 N1 C18 -169.19(18) . . . . ?
C6 S1 N1 C18 74.8(2) . . . . ?
C18 N1 C8 C12 2.5(2) . . . . ?
S1 N1 C8 C12 172.13(17) . . . . ?
C18 N1 C8 C9 -178.8(2) . . . . ?
S1 N1 C8 C9 -9.1(4) . . . . ?
O1 S1 C6 C5 -151.60(19) . . . . ?
O2 S1 C6 C5 -17.5(2) . . . . ?
N1 S1 C6 C5 95.5(2) . . . . ?
O1 S1 C6 C1 30.0(2) . . . . ?
O2 S1 C6 C1 164.0(2) . . . . ?
N1 S1 C6 C1 -82.9(2) . . . . ?
N1 C8 C12 C13 -2.1(3) . . . . ?
C9 C8 C12 C13 178.91(19) . . . . ?
N1 C8 C12 C11 176.3(2) . . . . ?
C9 C8 C12 C11 -2.7(3) . . . . ?
C14 C13 C12 C8 -177.6(3) . . . . ?
C18 C13 C12 C8 0.9(3) . . . . ?
C14 C13 C12 C11 4.7(5) . . . . ?
C18 C13 C12 C11 -176.9(3) . . . . ?
C14 C13 C18 C17 0.6(4) . . . . ?
C12 C13 C18 C17 -178.1(2) . . . . ?
C14 C13 C18 N1 179.4(2) . . . . ?
C12 C13 C18 N1 0.7(3) . . . . ?
C8 N1 C18 C17 176.7(3) . . . . ?
S1 N1 C18 C17 6.8(4) . . . . ?
C8 N1 C18 C13 -1.9(2) . . . . ?
S1 N1 C18 C13 -171.79(16) . . . . ?
C24 C19 C20 C21 1.4(4) . . . . ?
C9 C19 C20 C21 179.8(2) . . . . ?
C27 C26 C31 C30 0.7(3) . . . . ?
C10 C26 C31 C30 -179.2(2) . . . . ?
C1 C6 C5 C4 0.8(4) . . . . ?
S1 C6 C5 C4 -177.60(17) . . . . ?
C31 C26 C27 C28 0.6(3) . . . . ?
C10 C26 C27 C28 -179.6(2) . . . . ?
C30 C29 C28 C27 0.9(4) . . . . ?
C32 C29 C28 C27 -178.8(2) . . . . ?
C26 C27 C28 C29 -1.4(4) . . . . ?
C12 C8 C9 C19 -112.2(2) . . . . ?
N1 C8 C9 C19 69.1(3) . . . . ?
C12 C8 C9 C10 8.1(3) . . . . ?
N1 C8 C9 C10 -170.6(2) . . . . ?
C20 C19 C9 C8 47.2(3) . . . . ?
C24 C19 C9 C8 -134.6(2) . . . . ?
C20 C19 C9 C10 -66.6(3) . . . . ?
C24 C19 C9 C10 111.6(3) . . . . ?
C27 C26 C10 C11 -122.0(3) . . . . ?
C31 C26 C10 C11 57.9(3) . . . . ?
C27 C26 C10 C9 117.2(3) . . . . ?
C31 C26 C10 C9 -62.9(3) . . . . ?
C8 C9 C10 C26 113.6(2) . . . . ?
C19 C9 C10 C26 -123.3(2) . . . . ?
C8 C9 C10 C11 -9.9(2) . . . . ?
C19 C9 C10 C11 113.1(2) . . . . ?
C19 C20 C21 C22 -1.6(4) . . . . ?
C20 C19 C24 C23 -0.4(4) . . . . ?
C9 C19 C24 C23 -178.7(2) . . . . ?
C6 C5 C4 C3 1.1(4) . . . . ?
C13 C18 C17 C16 0.0(4) . . . . ?
N1 C18 C17 C16 -178.4(2) . . . . ?
C26 C31 C30 C29 -1.1(4) . . . . ?
C28 C29 C30 C31 0.3(4) . . . . ?
C32 C29 C30 C31 -179.9(2) . . . . ?
C18 C13 C14 C15 -1.2(4) . . . . ?
C12 C13 C14 C15 177.1(3) . . . . ?
C19 C24 C23 C22 -0.6(5) . . . . ?
C5 C6 C1 C2 -1.8(4) . . . . ?
S1 C6 C1 C2 176.7(2) . . . . ?
C5 C4 C3 C2 -2.0(4) . . . . ?
C5 C4 C3 C7 178.7(2) . . . . ?
C8 C12 C11 C10 -4.2(3) . . . . ?
C13 C12 C11 C10 173.5(3) . . . . ?
C26 C10 C11 C12 -114.4(2) . . . . ?
C9 C10 C11 C12 8.9(3) . . . . ?
C4 C3 C2 C1 1.0(5) . . . . ?
C7 C3 C2 C1 -179.7(3) . . . . ?
C6 C1 C2 C3 0.8(5) . . . . ?
C24 C23 C22 C21 0.5(5) . . . . ?
C24 C23 C22 C25 -178.3(3) . . . . ?
C20 C21 C22 C23 0.6(4) . . . . ?
C20 C21 C22 C25 179.4(3) . . . . ?
C13 C14 C15 C16 1.1(5) . . . . ?
C18 C17 C16 C15 -0.1(5) . . . . ?
C14 C15 C16 C17 -0.4(5) . . . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.177
_refine_diff_density_min         -0.229
_refine_diff_density_rms         0.040
####################################################################### 
# 
# 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_xx
_database_code_depnum_ccdc_archive 'CCDC 1414047'
_audit_update_record             
;
2015-07-21 deposited with the CCDC.
2015-12-24 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
2,2-Dimethyl-3-phenyl-4-tosyl-1,2,3,4-tetrahydrocyclopenta[b]indole
_chemical_name_common            6v
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C26 H25 N O2 S'
_chemical_formula_weight         415.53

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   P2(1)/n

loop_
_symmetry_equiv_pos_as_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                   13.926(2)
_cell_length_b                   10.6835(16)
_cell_length_c                   14.955(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 92.243(4)
_cell_angle_gamma                90.00
_cell_volume                     2223.2(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.15
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.241
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             880
_exptl_absorpt_coefficient_mu    0.168
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  0.9593
_exptl_absorpt_correction_T_max  0.9753
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            11734
_diffrn_reflns_av_R_equivalents  0.0545
_diffrn_reflns_av_sigmaI/netI    0.0542
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         1.96
_diffrn_reflns_theta_max         25.00
_reflns_number_total             3891
_reflns_number_gt                3019
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.0772P)²+0.1172P] 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     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3891
_refine_ls_number_parameters     274
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0630
_refine_ls_R_factor_gt           0.0467
_refine_ls_wR_factor_ref         0.1329
_refine_ls_wR_factor_gt          0.1242
_refine_ls_goodness_of_fit_ref   1.076
_refine_ls_restrained_S_all      1.076
_refine_ls_shift/su_max          0.002
_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 0.03953(3) 0.47347(5) 0.22245(3) 0.04245(18) Uani 1 1 d . . .
C6 C 0.17311(13) 0.36818(17) 0.11595(12) 0.0391(4) Uani 1 1 d . . .
C1 C 0.26733(13) 0.32014(17) 0.12674(12) 0.0392(4) Uani 1 1 d . . .
C5 C 0.12071(15) 0.3609(2) 0.03503(13) 0.0489(5) Uani 1 1 d . . .
H3 H 0.0592 0.3943 0.0283 0.059 Uiso 1 1 calc R . .
C2 C 0.30910(15) 0.2622(2) 0.05443(13) 0.0488(5) Uani 1 1 d . . .
H6 H 0.3713 0.2306 0.0598 0.059 Uiso 1 1 calc R . .
C3 C 0.25611(18) 0.2525(2) -0.02575(14) 0.0584(6) Uani 1 1 d . . .
H1 H 0.2827 0.2123 -0.0741 0.070 Uiso 1 1 calc R . .
C4 C 0.16431(17) 0.3015(2) -0.03501(14) 0.0591(6) Uani 1 1 d . . .
H2 H 0.1309 0.2944 -0.0899 0.071 Uiso 1 1 calc R . .
C8 C 0.22682(12) 0.40030(16) 0.26002(12) 0.0358(4) Uani 1 1 d . . .
C7 C 0.29846(12) 0.34528(17) 0.21741(13) 0.0402(4) Uani 1 1 d . . .
C10 C 0.36235(13) 0.41924(18) 0.35834(13) 0.0425(5) Uani 1 1 d . . .
C11 C 0.24817(12) 0.42846(18) 0.35680(12) 0.0391(4) Uani 1 1 d . . .
H11 H 0.2294 0.5150 0.3692 0.047 Uiso 1 1 calc R . .
C9 C 0.38667(14) 0.3331(2) 0.27810(14) 0.0503(5) Uani 1 1 d . . .
H9A H 0.4435 0.3622 0.2489 0.060 Uiso 1 1 calc R . .
H9B H 0.3965 0.2472 0.2973 0.060 Uiso 1 1 calc R . .
C14 C 0.19690(13) 0.34077(18) 0.41941(12) 0.0399(4) Uani 1 1 d . . .
C13 C 0.40708(16) 0.3714(2) 0.44629(15) 0.0593(6) Uani 1 1 d . . .
H14A H 0.4758 0.3748 0.4441 0.089 Uiso 1 1 calc R . .
H14B H 0.3872 0.2866 0.4557 0.089 Uiso 1 1 calc R . .
H14C H 0.3864 0.4228 0.4946 0.089 Uiso 1 1 calc R . .
C12 C 0.40054(16) 0.5509(2) 0.34146(16) 0.0589(6) Uani 1 1 d . . .
H13A H 0.3844 0.6047 0.3900 0.088 Uiso 1 1 calc R . .
H13B H 0.3721 0.5828 0.2866 0.088 Uiso 1 1 calc R . .
H13C H 0.4691 0.5478 0.3372 0.088 Uiso 1 1 calc R . .
N1 N 0.14689(10) 0.41816(15) 0.19958(10) 0.0381(4) Uani 1 1 d . . .
C15 C 0.14214(13) 0.3881(2) 0.48672(13) 0.0477(5) Uani 1 1 d . . .
H17 H 0.1381 0.4742 0.4944 0.057 Uiso 1 1 calc R . .
C19 C 0.20242(16) 0.21104(19) 0.41094(14) 0.0524(5) Uani 1 1 d . . .
H16 H 0.2388 0.1764 0.3663 0.063 Uiso 1 1 calc R . .
O2 O 0.05142(10) 0.52898(13) 0.30862(10) 0.0530(4) Uani 1 1 d . . .
O1 O 0.00796(11) 0.54582(13) 0.14701(10) 0.0586(4) Uani 1 1 d . . .
C20 C -0.03632(12) 0.34273(19) 0.22885(13) 0.0425(5) Uani 1 1 d . . .
C17 C 0.09920(18) 0.1821(3) 0.53321(17) 0.0681(7) Uani 1 1 d . . .
H21 H 0.0660 0.1292 0.5705 0.082 Uiso 1 1 calc R . .
C18 C 0.15462(18) 0.1334(2) 0.46795(17) 0.0668(7) Uani 1 1 d . . .
H19 H 0.1601 0.0471 0.4620 0.080 Uiso 1 1 calc R . .
C16 C 0.09315(16) 0.3096(3) 0.54305(15) 0.0605(6) Uani 1 1 d . . .
H20 H 0.0562 0.3433 0.5875 0.073 Uiso 1 1 calc R . .
C21 C -0.10303(14) 0.3188(2) 0.16026(14) 0.0534(5) Uani 1 1 d . . .
H22 H -0.1072 0.3703 0.1101 0.064 Uiso 1 1 calc R . .
C23 C -0.15762(17) 0.1384(2) 0.24060(18) 0.0662(7) Uani 1 1 d . . .
C25 C -0.03004(14) 0.2666(2) 0.30345(14) 0.0527(5) Uani 1 1 d . . .
H26 H 0.0144 0.2837 0.3498 0.063 Uiso 1 1 calc R . .
C22 C -0.16333(16) 0.2172(3) 0.16737(17) 0.0668(7) Uani 1 1 d . . .
H23 H -0.2090 0.2013 0.1217 0.080 Uiso 1 1 calc R . .
C24 C -0.09037(17) 0.1650(2) 0.30837(17) 0.0640(6) Uani 1 1 d . . .
H25 H -0.0858 0.1132 0.3583 0.077 Uiso 1 1 calc R . .
C26 C -0.2249(2) 0.0282(3) 0.2476(3) 0.1117(12) Uani 1 1 d . . .
H27A H -0.2717 0.0303 0.1987 0.168 Uiso 1 1 calc R . .
H27B H -0.2570 0.0326 0.3032 0.168 Uiso 1 1 calc R . .
H27C H -0.1889 -0.0482 0.2454 0.168 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
S1 O2 1.4223(14) . ?
S1 O1 1.4230(15) . ?
S1 N1 1.6557(15) . ?
S1 C20 1.756(2) . ?
C6 C5 1.391(3) . ?
C6 C1 1.412(3) . ?
C6 N1 1.421(2) . ?
C1 C2 1.393(3) . ?
C1 C7 1.433(3) . ?
C5 C4 1.385(3) . ?
C5 H3 0.9300 . ?
C2 C3 1.387(3) . ?
C2 H6 0.9300 . ?
C3 C4 1.384(3) . ?
C3 H1 0.9300 . ?
C4 H2 0.9300 . ?
C8 C7 1.340(2) . ?
C8 N1 1.419(2) . ?
C8 C11 1.497(2) . ?
C7 C9 1.504(3) . ?
C10 C13 1.521(3) . ?
C10 C12 1.528(3) . ?
C10 C9 1.560(3) . ?
C10 C11 1.592(2) . ?
C11 C14 1.522(3) . ?
C11 H11 0.9800 . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C14 C15 1.382(3) . ?
C14 C19 1.394(3) . ?
C13 H14A 0.9600 . ?
C13 H14B 0.9600 . ?
C13 H14C 0.9600 . ?
C12 H13A 0.9600 . ?
C12 H13B 0.9600 . ?
C12 H13C 0.9600 . ?
C15 C16 1.387(3) . ?
C15 H17 0.9300 . ?
C19 C18 1.379(3) . ?
C19 H16 0.9300 . ?
C20 C21 1.381(3) . ?
C20 C25 1.381(3) . ?
C17 C18 1.370(3) . ?
C17 C16 1.373(4) . ?
C17 H21 0.9300 . ?
C18 H19 0.9300 . ?
C16 H20 0.9300 . ?
C21 C22 1.379(3) . ?
C21 H22 0.9300 . ?
C23 C22 1.381(4) . ?
C23 C24 1.382(3) . ?
C23 C26 1.511(3) . ?
C25 C24 1.376(3) . ?
C25 H26 0.9300 . ?
C22 H23 0.9300 . ?
C24 H25 0.9300 . ?
C26 H27A 0.9600 . ?
C26 H27B 0.9600 . ?
C26 H27C 0.9600 . ?

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
O2 S1 O1 120.88(9) . . ?
O2 S1 N1 105.19(8) . . ?
O1 S1 N1 106.47(9) . . ?
O2 S1 C20 109.34(9) . . ?
O1 S1 C20 107.90(9) . . ?
N1 S1 C20 106.10(8) . . ?
C5 C6 C1 122.18(17) . . ?
C5 C6 N1 130.02(17) . . ?
C1 C6 N1 107.79(15) . . ?
C2 C1 C6 119.15(17) . . ?
C2 C1 C7 134.27(18) . . ?
C6 C1 C7 106.59(16) . . ?
C4 C5 C6 117.0(2) . . ?
C4 C5 H3 121.5 . . ?
C6 C5 H3 121.5 . . ?
C3 C2 C1 118.7(2) . . ?
C3 C2 H6 120.6 . . ?
C1 C2 H6 120.6 . . ?
C4 C3 C2 121.1(2) . . ?
C4 C3 H1 119.5 . . ?
C2 C3 H1 119.5 . . ?
C3 C4 C5 121.9(2) . . ?
C3 C4 H2 119.0 . . ?
C5 C4 H2 119.0 . . ?
C7 C8 N1 109.64(16) . . ?
C7 C8 C11 115.12(15) . . ?
N1 C8 C11 135.24(16) . . ?
C8 C7 C1 109.20(16) . . ?
C8 C7 C9 110.89(17) . . ?
C1 C7 C9 139.87(17) . . ?
C13 C10 C12 108.56(17) . . ?
C13 C10 C9 111.91(17) . . ?
C12 C10 C9 109.17(17) . . ?
C13 C10 C11 114.08(16) . . ?
C12 C10 C11 107.12(16) . . ?
C9 C10 C11 105.79(14) . . ?
C8 C11 C14 113.02(15) . . ?
C8 C11 C10 99.32(14) . . ?
C14 C11 C10 116.43(15) . . ?
C8 C11 H11 109.2 . . ?
C14 C11 H11 109.2 . . ?
C10 C11 H11 109.2 . . ?
C7 C9 C10 102.49(15) . . ?
C7 C9 H9A 111.3 . . ?
C10 C9 H9A 111.3 . . ?
C7 C9 H9B 111.3 . . ?
C10 C9 H9B 111.3 . . ?
H9A C9 H9B 109.2 . . ?
C15 C14 C19 117.6(2) . . ?
C15 C14 C11 120.57(18) . . ?
C19 C14 C11 121.81(17) . . ?
C10 C13 H14A 109.5 . . ?
C10 C13 H14B 109.5 . . ?
H14A C13 H14B 109.5 . . ?
C10 C13 H14C 109.5 . . ?
H14A C13 H14C 109.5 . . ?
H14B C13 H14C 109.5 . . ?
C10 C12 H13A 109.5 . . ?
C10 C12 H13B 109.5 . . ?
H13A C12 H13B 109.5 . . ?
C10 C12 H13C 109.5 . . ?
H13A C12 H13C 109.5 . . ?
H13B C12 H13C 109.5 . . ?
C8 N1 C6 106.74(14) . . ?
C8 N1 S1 127.49(13) . . ?
C6 N1 S1 125.54(12) . . ?
C14 C15 C16 121.3(2) . . ?
C14 C15 H17 119.3 . . ?
C16 C15 H17 119.3 . . ?
C18 C19 C14 120.8(2) . . ?
C18 C19 H16 119.6 . . ?
C14 C19 H16 119.6 . . ?
C21 C20 C25 120.7(2) . . ?
C21 C20 S1 119.72(17) . . ?
C25 C20 S1 119.57(15) . . ?
C18 C17 C16 119.4(2) . . ?
C18 C17 H21 120.3 . . ?
C16 C17 H21 120.3 . . ?
C17 C18 C19 120.8(2) . . ?
C17 C18 H19 119.6 . . ?
C19 C18 H19 119.6 . . ?
C17 C16 C15 120.1(2) . . ?
C17 C16 H20 120.0 . . ?
C15 C16 H20 120.0 . . ?
C22 C21 C20 118.9(2) . . ?
C22 C21 H22 120.6 . . ?
C20 C21 H22 120.6 . . ?
C22 C23 C24 118.2(2) . . ?
C22 C23 C26 120.9(2) . . ?
C24 C23 C26 120.9(3) . . ?
C24 C25 C20 119.2(2) . . ?
C24 C25 H26 120.4 . . ?
C20 C25 H26 120.4 . . ?
C21 C22 C23 121.6(2) . . ?
C21 C22 H23 119.2 . . ?
C23 C22 H23 119.2 . . ?
C25 C24 C23 121.4(2) . . ?
C25 C24 H25 119.3 . . ?
C23 C24 H25 119.3 . . ?
C23 C26 H27A 109.5 . . ?
C23 C26 H27B 109.5 . . ?
H27A C26 H27B 109.5 . . ?
C23 C26 H27C 109.5 . . ?
H27A C26 H27C 109.5 . . ?
H27B C26 H27C 109.5 . . ?

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
C5 C6 C1 C2 -0.7(3) . . . . ?
N1 C6 C1 C2 178.17(17) . . . . ?
C5 C6 C1 C7 179.44(17) . . . . ?
N1 C6 C1 C7 -1.7(2) . . . . ?
C1 C6 C5 C4 1.3(3) . . . . ?
N1 C6 C5 C4 -177.31(19) . . . . ?
C6 C1 C2 C3 -0.7(3) . . . . ?
C7 C1 C2 C3 179.1(2) . . . . ?
C1 C2 C3 C4 1.4(3) . . . . ?
C2 C3 C4 C5 -0.8(4) . . . . ?
C6 C5 C4 C3 -0.6(3) . . . . ?
N1 C8 C7 C1 -2.0(2) . . . . ?
C11 C8 C7 C1 178.13(15) . . . . ?
N1 C8 C7 C9 176.10(16) . . . . ?
C11 C8 C7 C9 -3.7(2) . . . . ?
C2 C1 C7 C8 -177.5(2) . . . . ?
C6 C1 C7 C8 2.3(2) . . . . ?
C2 C1 C7 C9 5.2(4) . . . . ?
C6 C1 C7 C9 -175.0(2) . . . . ?
C7 C8 C11 C14 -106.19(18) . . . . ?
N1 C8 C11 C14 74.0(3) . . . . ?
C7 C8 C11 C10 17.9(2) . . . . ?
N1 C8 C11 C10 -161.90(19) . . . . ?
C13 C10 C11 C8 -147.71(17) . . . . ?
C12 C10 C11 C8 92.12(18) . . . . ?
C9 C10 C11 C8 -24.26(18) . . . . ?
C13 C10 C11 C14 -26.1(2) . . . . ?
C12 C10 C11 C14 -146.28(17) . . . . ?
C9 C10 C11 C14 97.35(18) . . . . ?
C8 C7 C9 C10 -12.8(2) . . . . ?
C1 C7 C9 C10 164.5(2) . . . . ?
C13 C10 C9 C7 147.86(17) . . . . ?
C12 C10 C9 C7 -91.93(18) . . . . ?
C11 C10 C9 C7 23.1(2) . . . . ?
C8 C11 C14 C15 -127.70(18) . . . . ?
C10 C11 C14 C15 118.24(19) . . . . ?
C8 C11 C14 C19 51.7(2) . . . . ?
C10 C11 C14 C19 -62.3(2) . . . . ?
C7 C8 N1 C6 1.0(2) . . . . ?
C11 C8 N1 C6 -179.25(19) . . . . ?
C7 C8 N1 S1 175.54(14) . . . . ?
C11 C8 N1 S1 -4.7(3) . . . . ?
C5 C6 N1 C8 179.27(19) . . . . ?
C1 C6 N1 C8 0.48(19) . . . . ?
C5 C6 N1 S1 4.6(3) . . . . ?
C1 C6 N1 S1 -174.22(13) . . . . ?
O2 S1 N1 C8 14.63(18) . . . . ?
O1 S1 N1 C8 144.03(15) . . . . ?
C20 S1 N1 C8 -101.20(16) . . . . ?
O2 S1 N1 C6 -171.77(15) . . . . ?
O1 S1 N1 C6 -42.37(17) . . . . ?
C20 S1 N1 C6 72.40(17) . . . . ?
C19 C14 C15 C16 -1.0(3) . . . . ?
C11 C14 C15 C16 178.49(18) . . . . ?
C15 C14 C19 C18 0.1(3) . . . . ?
C11 C14 C19 C18 -179.4(2) . . . . ?
O2 S1 C20 C21 141.05(16) . . . . ?
O1 S1 C20 C21 7.82(19) . . . . ?
N1 S1 C20 C21 -105.97(16) . . . . ?
O2 S1 C20 C25 -37.49(18) . . . . ?
O1 S1 C20 C25 -170.72(16) . . . . ?
N1 S1 C20 C25 75.49(17) . . . . ?
C16 C17 C18 C19 -1.5(4) . . . . ?
C14 C19 C18 C17 1.2(4) . . . . ?
C18 C17 C16 C15 0.6(4) . . . . ?
C14 C15 C16 C17 0.7(3) . . . . ?
C25 C20 C21 C22 -0.1(3) . . . . ?
S1 C20 C21 C22 -178.64(17) . . . . ?
C21 C20 C25 C24 0.8(3) . . . . ?
S1 C20 C25 C24 179.37(17) . . . . ?
C20 C21 C22 C23 -0.9(4) . . . . ?
C24 C23 C22 C21 1.1(4) . . . . ?
C26 C23 C22 C21 179.4(3) . . . . ?
C20 C25 C24 C23 -0.6(3) . . . . ?
C22 C23 C24 C25 -0.4(4) . . . . ?
C26 C23 C24 C25 -178.7(3) . . . . ?

_diffrn_measured_fraction_theta_max 0.995
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.995
_refine_diff_density_max         0.199
_refine_diff_density_min         -0.407
_refine_diff_density_rms         0.058

####################################################################### 
# 
# 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_xxz42
_database_code_depnum_ccdc_archive 'CCDC 1414048'
_audit_update_record             
;
2015-07-21 deposited with the CCDC.
2015-12-24 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
N-(2-(trans-5-ethoxy-3-phenylcyclopent-1-en-1-yl)phenyl)-4-methylbenzenesulfonamide
_chemical_name_common            9
_chemical_melting_point          ?
_chemical_formula_moiety         'C26 H27 N O3 S'
_chemical_formula_sum            'C26 H27 N O3 S'
_chemical_formula_weight         433.55

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   P2(1)/n

loop_
_symmetry_equiv_pos_as_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                   10.4657(14)
_cell_length_b                   19.751(3)
_cell_length_c                   12.477(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 114.712(3)
_cell_angle_gamma                90.00
_cell_volume                     2343.0(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    2352
_cell_measurement_theta_min      2.38
_cell_measurement_theta_max      21.68

_exptl_crystal_description       BLOCK
_exptl_crystal_colour            COLORLESS
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.15
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.229
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             920
_exptl_absorpt_coefficient_mu    0.165
_exptl_absorpt_correction_type   MULTI-SCAN
_exptl_absorpt_correction_T_min  0.9600
_exptl_absorpt_correction_T_max  0.9757
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            12936
_diffrn_reflns_av_R_equivalents  0.0623
_diffrn_reflns_av_sigmaI/netI    0.0703
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.06
_diffrn_reflns_theta_max         25.00
_reflns_number_total             4121
_reflns_number_gt                2302
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.0767P)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     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         4121
_refine_ls_number_parameters     286
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1089
_refine_ls_R_factor_gt           0.0527
_refine_ls_wR_factor_ref         0.1570
_refine_ls_wR_factor_gt          0.1305
_refine_ls_goodness_of_fit_ref   1.003
_refine_ls_restrained_S_all      1.003
_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 -0.31606(7) 0.36127(4) 0.61565(7) 0.0673(3) Uani 1 1 d . . .
O3 O 0.0746(2) 0.38653(12) 0.64027(17) 0.0790(6) Uani 1 1 d . . .
C8 C -0.1763(3) 0.47870(15) 0.6739(2) 0.0563(7) Uani 1 1 d . . .
C15 C 0.1247(3) 0.41074(15) 0.9105(2) 0.0654(8) Uani 1 1 d . . .
H15 H 0.0858 0.4139 0.9651 0.078 Uiso 1 1 calc R . .
C5 C -0.2693(3) 0.33828(13) 0.7635(2) 0.0549(7) Uani 1 1 d . . .
C12 C -0.0299(3) 0.55499(17) 0.8247(3) 0.0729(8) Uani 1 1 d . . .
H12 H 0.0552 0.5652 0.8876 0.088 Uiso 1 1 calc R . .
N N -0.1999(3) 0.41592(14) 0.6130(2) 0.0653(7) Uani 1 1 d . . .
C16 C 0.2507(3) 0.36763(16) 0.9311(3) 0.0698(8) Uani 1 1 d . . .
H16 H 0.2228 0.3199 0.9219 0.084 Uiso 1 1 calc R . .
C13 C -0.0456(3) 0.49246(15) 0.7680(2) 0.0592(7) Uani 1 1 d . . .
C18 C 0.1581(3) 0.42697(18) 0.7398(3) 0.0722(9) Uani 1 1 d . . .
H18 H 0.1875 0.4687 0.7140 0.087 Uiso 1 1 calc R . .
C17 C 0.2863(3) 0.3890(2) 0.8277(3) 0.0957(12) Uani 1 1 d . . .
H17A H 0.3685 0.4181 0.8558 0.115 Uiso 1 1 calc R . .
H17B H 0.3057 0.3495 0.7908 0.115 Uiso 1 1 calc R . .
C14 C 0.0730(3) 0.44377(15) 0.8097(2) 0.0588(7) Uani 1 1 d . . .
C21 C 0.3731(3) 0.37771(15) 1.0505(3) 0.0604(8) Uani 1 1 d . . .
C22 C 0.4463(3) 0.32288(17) 1.1177(3) 0.0754(9) Uani 1 1 d . . .
H22 H 0.4205 0.2791 1.0897 0.090 Uiso 1 1 calc R . .
C25 C 0.5254(4) 0.4501(2) 1.2064(3) 0.0996(12) Uani 1 1 d . . .
H25 H 0.5516 0.4936 1.2361 0.120 Uiso 1 1 calc R . .
C26 C 0.4147(3) 0.44129(18) 1.0967(3) 0.0900(10) Uani 1 1 d . . .
H26 H 0.3677 0.4790 1.0536 0.108 Uiso 1 1 calc R . .
O2 O -0.44890(19) 0.39501(11) 0.57484(19) 0.0835(7) Uani 1 1 d . . .
O1 O -0.2996(2) 0.30303(11) 0.55370(19) 0.0901(7) Uani 1 1 d . . .
C20 C 0.0184(5) 0.3471(3) 0.4467(3) 0.1425(19) Uani 1 1 d . . .
H20A H 0.0408 0.3007 0.4697 0.214 Uiso 1 1 calc R . .
H20B H 0.0322 0.3558 0.3765 0.214 Uiso 1 1 calc R . .
H20C H -0.0779 0.3558 0.4314 0.214 Uiso 1 1 calc R . .
C19 C 0.1116(4) 0.3922(2) 0.5432(3) 0.1015(13) Uani 1 1 d . . .
H19A H 0.2091 0.3791 0.5673 0.122 Uiso 1 1 calc R . .
H19B H 0.1008 0.4387 0.5158 0.122 Uiso 1 1 calc R . .
C10 C -0.2628(3) 0.58776(18) 0.6946(3) 0.0769(9) Uani 1 1 d . . .
H10 H -0.3346 0.6197 0.6693 0.092 Uiso 1 1 calc R . .
C9 C -0.2815(3) 0.52741(17) 0.6382(3) 0.0694(8) Uani 1 1 d . . .
H9 H -0.3665 0.5185 0.5743 0.083 Uiso 1 1 calc R . .
C11 C -0.1370(4) 0.60178(17) 0.7896(3) 0.0796(9) Uani 1 1 d . . .
H11 H -0.1249 0.6426 0.8297 0.095 Uiso 1 1 calc R . .
C2 C -0.1985(3) 0.29912(16) 0.9960(3) 0.0693(8) Uani 1 1 d . . .
C6 C -0.1686(3) 0.28990(17) 0.8159(3) 0.0825(10) Uani 1 1 d . . .
H6 H -0.1232 0.2699 0.7739 0.099 Uiso 1 1 calc R . .
C3 C -0.2980(4) 0.34819(19) 0.9425(4) 0.0901(11) Uani 1 1 d . . .
H3 H -0.3422 0.3687 0.9850 0.108 Uiso 1 1 calc R . .
C7 C -0.1344(4) 0.27075(16) 0.9312(3) 0.0839(10) Uani 1 1 d . . .
H7 H -0.0661 0.2377 0.9656 0.101 Uiso 1 1 calc R . .
C4 C -0.3336(3) 0.36757(15) 0.8287(3) 0.0767(9) Uani 1 1 d . . .
H4 H -0.4017 0.4008 0.7947 0.092 Uiso 1 1 calc R . .
C1 C -0.1611(4) 0.2767(2) 1.1207(3) 0.1075(13) Uani 1 1 d . . .
H1A H -0.2320 0.2463 1.1221 0.161 Uiso 1 1 calc R . .
H1B H -0.1557 0.3155 1.1688 0.161 Uiso 1 1 calc R . .
H1C H -0.0718 0.2541 1.1510 0.161 Uiso 1 1 calc R . .
C24 C 0.5957(3) 0.3961(2) 1.2708(3) 0.0931(11) Uani 1 1 d . . .
H24 H 0.6692 0.4025 1.3448 0.112 Uiso 1 1 calc R . .
C23 C 0.5593(3) 0.3334(2) 1.2278(3) 0.0896(11) Uani 1 1 d . . .
H23 H 0.6094 0.2965 1.2714 0.108 Uiso 1 1 calc R . .
H1' H -0.139(3) 0.3905(13) 0.616(2) 0.056(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
S1 O2 1.430(2) . ?
S1 O1 1.436(2) . ?
S1 N 1.636(3) . ?
S1 C5 1.760(3) . ?
O3 C19 1.422(4) . ?
O3 C18 1.427(4) . ?
C8 C9 1.388(4) . ?
C8 C13 1.407(4) . ?
C8 N 1.421(4) . ?
C15 C14 1.316(4) . ?
C15 C16 1.499(4) . ?
C15 H15 0.9300 . ?
C5 C6 1.369(4) . ?
C5 C4 1.380(4) . ?
C12 C11 1.376(4) . ?
C12 C13 1.398(4) . ?
C12 H12 0.9300 . ?
N H1' 0.80(2) . ?
C16 C21 1.518(4) . ?
C16 C17 1.544(4) . ?
C16 H16 0.9800 . ?
C13 C14 1.483(4) . ?
C18 C14 1.520(4) . ?
C18 C17 1.528(4) . ?
C18 H18 0.9800 . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C21 C26 1.374(4) . ?
C21 C22 1.388(4) . ?
C22 C23 1.404(5) . ?
C22 H22 0.9300 . ?
C25 C24 1.353(5) . ?
C25 C26 1.386(5) . ?
C25 H25 0.9300 . ?
C26 H26 0.9300 . ?
C20 C19 1.487(6) . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
C19 H19A 0.9700 . ?
C19 H19B 0.9700 . ?
C10 C9 1.356(4) . ?
C10 C11 1.382(5) . ?
C10 H10 0.9300 . ?
C9 H9 0.9300 . ?
C11 H11 0.9300 . ?
C2 C7 1.368(4) . ?
C2 C3 1.374(4) . ?
C2 C1 1.504(4) . ?
C6 C7 1.382(4) . ?
C6 H6 0.9300 . ?
C3 C4 1.364(5) . ?
C3 H3 0.9300 . ?
C7 H7 0.9300 . ?
C4 H4 0.9300 . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C24 C23 1.339(5) . ?
C24 H24 0.9300 . ?
C23 H23 0.9300 . ?

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
O2 S1 O1 119.95(13) . . ?
O2 S1 N 107.80(14) . . ?
O1 S1 N 105.09(15) . . ?
O2 S1 C5 107.24(13) . . ?
O1 S1 C5 108.32(13) . . ?
N S1 C5 107.94(12) . . ?
C19 O3 C18 114.3(3) . . ?
C9 C8 C13 119.9(3) . . ?
C9 C8 N 119.7(3) . . ?
C13 C8 N 120.4(3) . . ?
C14 C15 C16 115.2(3) . . ?
C14 C15 H15 122.4 . . ?
C16 C15 H15 122.4 . . ?
C6 C5 C4 118.6(3) . . ?
C6 C5 S1 120.1(2) . . ?
C4 C5 S1 121.3(2) . . ?
C11 C12 C13 121.6(3) . . ?
C11 C12 H12 119.2 . . ?
C13 C12 H12 119.2 . . ?
C8 N S1 121.9(2) . . ?
C8 N H1' 124(2) . . ?
S1 N H1' 99.7(19) . . ?
C15 C16 C21 114.5(3) . . ?
C15 C16 C17 101.8(2) . . ?
C21 C16 C17 112.6(2) . . ?
C15 C16 H16 109.2 . . ?
C21 C16 H16 109.2 . . ?
C17 C16 H16 109.2 . . ?
C12 C13 C8 117.4(3) . . ?
C12 C13 C14 119.4(2) . . ?
C8 C13 C14 123.2(3) . . ?
O3 C18 C14 109.2(2) . . ?
O3 C18 C17 112.6(3) . . ?
C14 C18 C17 104.2(2) . . ?
O3 C18 H18 110.2 . . ?
C14 C18 H18 110.2 . . ?
C17 C18 H18 110.2 . . ?
C18 C17 C16 106.7(2) . . ?
C18 C17 H17A 110.4 . . ?
C16 C17 H17A 110.4 . . ?
C18 C17 H17B 110.4 . . ?
C16 C17 H17B 110.4 . . ?
H17A C17 H17B 108.6 . . ?
C15 C14 C13 127.3(3) . . ?
C15 C14 C18 109.6(2) . . ?
C13 C14 C18 123.1(2) . . ?
C26 C21 C22 117.5(3) . . ?
C26 C21 C16 121.4(3) . . ?
C22 C21 C16 121.1(3) . . ?
C21 C22 C23 120.1(3) . . ?
C21 C22 H22 119.9 . . ?
C23 C22 H22 119.9 . . ?
C24 C25 C26 120.7(4) . . ?
C24 C25 H25 119.6 . . ?
C26 C25 H25 119.6 . . ?
C21 C26 C25 121.1(3) . . ?
C21 C26 H26 119.5 . . ?
C25 C26 H26 119.5 . . ?
C19 C20 H20A 109.5 . . ?
C19 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C19 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
O3 C19 C20 108.8(3) . . ?
O3 C19 H19A 109.9 . . ?
C20 C19 H19A 109.9 . . ?
O3 C19 H19B 109.9 . . ?
C20 C19 H19B 109.9 . . ?
H19A C19 H19B 108.3 . . ?
C9 C10 C11 120.0(3) . . ?
C9 C10 H10 120.0 . . ?
C11 C10 H10 120.0 . . ?
C10 C9 C8 121.3(3) . . ?
C10 C9 H9 119.4 . . ?
C8 C9 H9 119.4 . . ?
C12 C11 C10 119.7(3) . . ?
C12 C11 H11 120.2 . . ?
C10 C11 H11 120.2 . . ?
C7 C2 C3 117.5(3) . . ?
C7 C2 C1 120.8(3) . . ?
C3 C2 C1 121.8(3) . . ?
C5 C6 C7 120.0(3) . . ?
C5 C6 H6 120.0 . . ?
C7 C6 H6 120.0 . . ?
C4 C3 C2 121.7(3) . . ?
C4 C3 H3 119.2 . . ?
C2 C3 H3 119.2 . . ?
C2 C7 C6 121.7(3) . . ?
C2 C7 H7 119.2 . . ?
C6 C7 H7 119.2 . . ?
C3 C4 C5 120.5(3) . . ?
C3 C4 H4 119.8 . . ?
C5 C4 H4 119.8 . . ?
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C23 C24 C25 119.8(3) . . ?
C23 C24 H24 120.1 . . ?
C25 C24 H24 120.1 . . ?
C24 C23 C22 120.8(3) . . ?
C24 C23 H23 119.6 . . ?
C22 C23 H23 119.6 . . ?

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
O2 S1 C5 C6 162.1(2) . . . . ?
O1 S1 C5 C6 31.3(3) . . . . ?
N S1 C5 C6 -82.0(3) . . . . ?
O2 S1 C5 C4 -17.1(3) . . . . ?
O1 S1 C5 C4 -147.9(2) . . . . ?
N S1 C5 C4 98.8(3) . . . . ?
C9 C8 N S1 -66.4(3) . . . . ?
C13 C8 N S1 115.4(3) . . . . ?
O2 S1 N C8 55.9(2) . . . . ?
O1 S1 N C8 -175.0(2) . . . . ?
C5 S1 N C8 -59.6(2) . . . . ?
C14 C15 C16 C21 130.7(3) . . . . ?
C14 C15 C16 C17 9.0(4) . . . . ?
C11 C12 C13 C8 -0.6(4) . . . . ?
C11 C12 C13 C14 -179.7(3) . . . . ?
C9 C8 C13 C12 2.3(4) . . . . ?
N C8 C13 C12 -179.5(2) . . . . ?
C9 C8 C13 C14 -178.6(2) . . . . ?
N C8 C13 C14 -0.4(4) . . . . ?
C19 O3 C18 C14 153.4(3) . . . . ?
C19 O3 C18 C17 -91.4(3) . . . . ?
O3 C18 C17 C16 -102.4(3) . . . . ?
C14 C18 C17 C16 15.8(4) . . . . ?
C15 C16 C17 C18 -15.0(4) . . . . ?
C21 C16 C17 C18 -138.0(3) . . . . ?
C16 C15 C14 C13 -176.8(3) . . . . ?
C16 C15 C14 C18 1.0(4) . . . . ?
C12 C13 C14 C15 68.2(4) . . . . ?
C8 C13 C14 C15 -110.9(3) . . . . ?
C12 C13 C14 C18 -109.3(3) . . . . ?
C8 C13 C14 C18 71.6(4) . . . . ?
O3 C18 C14 C15 109.8(3) . . . . ?
C17 C18 C14 C15 -10.7(4) . . . . ?
O3 C18 C14 C13 -72.3(3) . . . . ?
C17 C18 C14 C13 167.1(3) . . . . ?
C15 C16 C21 C26 -43.7(4) . . . . ?
C17 C16 C21 C26 72.0(4) . . . . ?
C15 C16 C21 C22 135.6(3) . . . . ?
C17 C16 C21 C22 -108.8(3) . . . . ?
C26 C21 C22 C23 -0.8(4) . . . . ?
C16 C21 C22 C23 180.0(3) . . . . ?
C22 C21 C26 C25 -0.1(5) . . . . ?
C16 C21 C26 C25 179.2(3) . . . . ?
C24 C25 C26 C21 0.1(6) . . . . ?
C18 O3 C19 C20 179.3(3) . . . . ?
C11 C10 C9 C8 0.1(5) . . . . ?
C13 C8 C9 C10 -2.1(4) . . . . ?
N C8 C9 C10 179.7(3) . . . . ?
C13 C12 C11 C10 -1.4(5) . . . . ?
C9 C10 C11 C12 1.7(5) . . . . ?
C4 C5 C6 C7 0.8(5) . . . . ?
S1 C5 C6 C7 -178.5(3) . . . . ?
C7 C2 C3 C4 0.9(5) . . . . ?
C1 C2 C3 C4 -178.8(3) . . . . ?
C3 C2 C7 C6 -0.6(5) . . . . ?
C1 C2 C7 C6 179.1(3) . . . . ?
C5 C6 C7 C2 -0.2(5) . . . . ?
C2 C3 C4 C5 -0.3(5) . . . . ?
C6 C5 C4 C3 -0.5(5) . . . . ?
S1 C5 C4 C3 178.7(3) . . . . ?
C26 C25 C24 C23 0.8(6) . . . . ?
C25 C24 C23 C22 -1.7(6) . . . . ?
C21 C22 C23 C24 1.7(5) . . . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.188
_refine_diff_density_min         -0.299
_refine_diff_density_rms         0.050
####################################################################### 
# 
# 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_xxz08
_database_code_depnum_ccdc_archive 'CCDC 1414049'
_audit_update_record             
;
2015-07-21 deposited with the CCDC.
2015-12-24 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
2-Phenyl-4-tosyl-2,3,3a,4-tetrahydrocyclopenta[b]indole
_chemical_name_common            10
_chemical_melting_point          ?
_chemical_formula_moiety         'C24 H21 N O2 S'
_chemical_formula_sum            'C24 H21 N O2 S'
_chemical_formula_weight         387.48

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   P2(1)/c

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

_cell_length_a                   10.6663(11)
_cell_length_b                   10.8826(12)
_cell_length_c                   18.121(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 103.780(2)
_cell_angle_gamma                90.00
_cell_volume                     2042.9(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.15
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.260
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             816
_exptl_absorpt_coefficient_mu    0.177
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9570
_exptl_absorpt_correction_T_max  0.9739
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            10994
_diffrn_reflns_av_R_equivalents  0.0377
_diffrn_reflns_av_sigmaI/netI    0.0396
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         1.97
_diffrn_reflns_theta_max         25.00
_reflns_number_total             3583
_reflns_number_gt                2751
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.0803P)²+0.1552P] 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     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3583
_refine_ls_number_parameters     254
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0613
_refine_ls_R_factor_gt           0.0434
_refine_ls_wR_factor_ref         0.1340
_refine_ls_wR_factor_gt          0.1230
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_restrained_S_all      1.055
_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 0.05752(5) 0.19481(4) 0.21695(3) 0.04448(19) Uani 1 1 d . . .
C12 C 0.13148(16) 0.22858(17) 0.08478(10) 0.0406(4) Uani 1 1 d . . .
C13 C 0.14539(16) 0.15498(17) 0.02319(10) 0.0410(4) Uani 1 1 d . . .
C14 C 0.1584(2) 0.2097(2) -0.04327(12) 0.0536(5) Uani 1 1 d . . .
H4 H 0.1677 0.1619 -0.0842 0.064 Uiso 1 1 calc R . .
C17 C 0.1324(2) 0.35453(19) 0.08013(13) 0.0571(5) Uani 1 1 d . . .
H1 H 0.1252 0.4033 0.1211 0.069 Uiso 1 1 calc R . .
C15 C 0.1575(2) 0.3360(2) -0.04820(13) 0.0653(6) Uani 1 1 d . . .
H5 H 0.1658 0.3737 -0.0929 0.078 Uiso 1 1 calc R . .
C16 C 0.1446(2) 0.4065(2) 0.01216(14) 0.0672(6) Uani 1 1 d . . .
H6 H 0.1438 0.4917 0.0075 0.081 Uiso 1 1 calc R . .
O2 O 0.10446(15) 0.31483(13) 0.24097(8) 0.0606(4) Uani 1 1 d . . .
N1 N 0.12767(14) 0.15249(13) 0.14899(8) 0.0399(4) Uani 1 1 d . . .
O1 O 0.07931(15) 0.09537(14) 0.26956(7) 0.0600(4) Uani 1 1 d . . .
C18 C -0.10895(19) 0.20420(17) 0.17683(11) 0.0440(5) Uani 1 1 d . . .
C10 C 0.10602(17) 0.02326(15) 0.12038(10) 0.0394(4) Uani 1 1 d . . .
H10 H 0.0137 0.0038 0.1085 0.047 Uiso 1 1 calc R . .
C9 C 0.15263(16) 0.02793(17) 0.04913(10) 0.0396(4) Uani 1 1 d . . .
C8 C 0.20819(19) -0.07790(18) 0.03772(11) 0.0488(5) Uani 1 1 d . . .
H12 H 0.2421 -0.0944 -0.0040 0.059 Uiso 1 1 calc R . .
C19 C -0.1626(2) 0.31019(19) 0.14000(13) 0.0574(6) Uani 1 1 d . . .
H20 H -0.1108 0.3778 0.1368 0.069 Uiso 1 1 calc R . .
C7 C 0.20884(19) -0.16728(17) 0.10147(12) 0.0493(5) Uani 1 1 d . . .
H13 H 0.1356 -0.2236 0.0857 0.059 Uiso 1 1 calc R . .
C20 C -0.2936(2) 0.3145(2) 0.10813(16) 0.0736(7) Uani 1 1 d . . .
H19 H -0.3294 0.3849 0.0824 0.088 Uiso 1 1 calc R . .
C11 C 0.1832(2) -0.08136(17) 0.16523(11) 0.0521(5) Uani 1 1 d . . .
H14A H 0.1339 -0.1233 0.1962 0.062 Uiso 1 1 calc R . .
H14B H 0.2634 -0.0518 0.1976 0.062 Uiso 1 1 calc R . .
C23 C -0.1865(2) 0.1040(2) 0.18199(13) 0.0609(6) Uani 1 1 d . . .
H16 H -0.1508 0.0324 0.2062 0.073 Uiso 1 1 calc R . .
C21 C -0.3727(2) 0.2157(3) 0.11375(18) 0.0800(8) Uani 1 1 d . . .
C22 C -0.3171(2) 0.1120(3) 0.15076(17) 0.0797(8) Uani 1 1 d . . .
H17 H -0.3694 0.0451 0.1549 0.096 Uiso 1 1 calc R . .
C4 C 0.3314(2) -0.24217(19) 0.12661(12) 0.0541(5) Uani 1 1 d . . .
C24 C -0.5175(3) 0.2215(4) 0.0793(3) 0.1381(16) Uani 1 1 d . . .
H21A H -0.5430 0.1527 0.0459 0.207 Uiso 1 1 calc R . .
H21B H -0.5380 0.2965 0.0512 0.207 Uiso 1 1 calc R . .
H21C H -0.5628 0.2189 0.1192 0.207 Uiso 1 1 calc R . .
C5 C 0.3289(3) -0.3621(2) 0.14520(17) 0.0825(8) Uani 1 1 d . . .
H23 H 0.2499 -0.4011 0.1411 0.099 Uiso 1 1 calc R . .
C1 C 0.5594(4) -0.3725(4) 0.1770(2) 0.1100(12) Uani 1 1 d . . .
H26 H 0.6356 -0.4172 0.1919 0.132 Uiso 1 1 calc R . .
C3 C 0.4502(3) -0.1877(3) 0.1356(2) 0.1156(13) Uani 1 1 d . . .
H24 H 0.4548 -0.1049 0.1239 0.139 Uiso 1 1 calc R . .
C2 C 0.5639(3) -0.2536(4) 0.1620(3) 0.1408(17) Uani 1 1 d . . .
H25 H 0.6432 -0.2141 0.1690 0.169 Uiso 1 1 calc R . .
C6 C 0.4438(4) -0.4290(3) 0.1706(2) 0.1154(12) Uani 1 1 d . . .
H27 H 0.4407 -0.5117 0.1831 0.138 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
S1 O1 1.4243(14) . ?
S1 O2 1.4291(14) . ?
S1 N1 1.6515(15) . ?
S1 C18 1.754(2) . ?
C12 C17 1.373(3) . ?
C12 C13 1.410(3) . ?
C12 N1 1.437(2) . ?
C13 C14 1.380(3) . ?
C13 C9 1.456(3) . ?
C14 C15 1.377(3) . ?
C14 H4 0.9300 . ?
C17 C16 1.389(3) . ?
C17 H1 0.9300 . ?
C15 C16 1.370(3) . ?
C15 H5 0.9300 . ?
C16 H6 0.9300 . ?
N1 C10 1.498(2) . ?
C18 C23 1.385(3) . ?
C18 C19 1.386(3) . ?
C10 C9 1.491(3) . ?
C10 C11 1.522(3) . ?
C10 H10 0.9800 . ?
C9 C8 1.334(3) . ?
C8 C7 1.509(3) . ?
C8 H12 0.9300 . ?
C19 C20 1.380(3) . ?
C19 H20 0.9300 . ?
C7 C4 1.516(3) . ?
C7 C11 1.560(3) . ?
C7 H13 0.9800 . ?
C20 C21 1.386(4) . ?
C20 H19 0.9300 . ?
C11 H14A 0.9700 . ?
C11 H14B 0.9700 . ?
C23 C22 1.376(3) . ?
C23 H16 0.9300 . ?
C21 C22 1.373(4) . ?
C21 C24 1.523(4) . ?
C22 H17 0.9300 . ?
C4 C5 1.350(3) . ?
C4 C3 1.373(4) . ?
C24 H21A 0.9600 . ?
C24 H21B 0.9600 . ?
C24 H21C 0.9600 . ?
C5 C6 1.406(4) . ?
C5 H23 0.9300 . ?
C1 C2 1.325(5) . ?
C1 C6 1.358(5) . ?
C1 H26 0.9300 . ?
C3 C2 1.392(4) . ?
C3 H24 0.9300 . ?
C2 H25 0.9300 . ?
C6 H27 0.9300 . ?

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
O1 S1 O2 120.06(9) . . ?
O1 S1 N1 104.87(8) . . ?
O2 S1 N1 107.10(9) . . ?
O1 S1 C18 108.02(9) . . ?
O2 S1 C18 108.64(9) . . ?
N1 S1 C18 107.51(8) . . ?
C17 C12 C13 120.98(17) . . ?
C17 C12 N1 128.82(17) . . ?
C13 C12 N1 110.01(16) . . ?
C14 C13 C12 119.81(18) . . ?
C14 C13 C9 133.06(18) . . ?
C12 C13 C9 106.94(15) . . ?
C15 C14 C13 119.1(2) . . ?
C15 C14 H4 120.4 . . ?
C13 C14 H4 120.4 . . ?
C12 C17 C16 117.7(2) . . ?
C12 C17 H1 121.2 . . ?
C16 C17 H1 121.2 . . ?
C16 C15 C14 120.5(2) . . ?
C16 C15 H5 119.7 . . ?
C14 C15 H5 119.7 . . ?
C15 C16 C17 121.9(2) . . ?
C15 C16 H6 119.1 . . ?
C17 C16 H6 119.1 . . ?
C12 N1 C10 107.02(13) . . ?
C12 N1 S1 123.26(12) . . ?
C10 N1 S1 117.40(11) . . ?
C23 C18 C19 120.2(2) . . ?
C23 C18 S1 119.21(16) . . ?
C19 C18 S1 120.60(16) . . ?
C9 C10 N1 102.24(13) . . ?
C9 C10 C11 103.80(14) . . ?
N1 C10 C11 119.90(15) . . ?
C9 C10 H10 110.1 . . ?
N1 C10 H10 110.1 . . ?
C11 C10 H10 110.1 . . ?
C8 C9 C13 139.56(18) . . ?
C8 C9 C10 110.91(17) . . ?
C13 C9 C10 108.00(15) . . ?
C9 C8 C7 111.05(17) . . ?
C9 C8 H12 124.5 . . ?
C7 C8 H12 124.5 . . ?
C20 C19 C18 119.4(2) . . ?
C20 C19 H20 120.3 . . ?
C18 C19 H20 120.3 . . ?
C8 C7 C4 115.03(17) . . ?
C8 C7 C11 102.18(15) . . ?
C4 C7 C11 112.98(17) . . ?
C8 C7 H13 108.8 . . ?
C4 C7 H13 108.8 . . ?
C11 C7 H13 108.8 . . ?
C19 C20 C21 121.1(2) . . ?
C19 C20 H19 119.4 . . ?
C21 C20 H19 119.4 . . ?
C10 C11 C7 102.75(15) . . ?
C10 C11 H14A 111.2 . . ?
C7 C11 H14A 111.2 . . ?
C10 C11 H14B 111.2 . . ?
C7 C11 H14B 111.2 . . ?
H14A C11 H14B 109.1 . . ?
C22 C23 C18 119.0(2) . . ?
C22 C23 H16 120.5 . . ?
C18 C23 H16 120.5 . . ?
C22 C21 C20 118.3(2) . . ?
C22 C21 C24 120.8(3) . . ?
C20 C21 C24 120.9(3) . . ?
C21 C22 C23 122.0(2) . . ?
C21 C22 H17 119.0 . . ?
C23 C22 H17 119.0 . . ?
C5 C4 C3 117.4(2) . . ?
C5 C4 C7 121.9(2) . . ?
C3 C4 C7 120.6(2) . . ?
C21 C24 H21A 109.5 . . ?
C21 C24 H21B 109.5 . . ?
H21A C24 H21B 109.5 . . ?
C21 C24 H21C 109.5 . . ?
H21A C24 H21C 109.5 . . ?
H21B C24 H21C 109.5 . . ?
C4 C5 C6 121.0(3) . . ?
C4 C5 H23 119.5 . . ?
C6 C5 H23 119.5 . . ?
C2 C1 C6 120.1(3) . . ?
C2 C1 H26 120.0 . . ?
C6 C1 H26 120.0 . . ?
C4 C3 C2 121.5(3) . . ?
C4 C3 H24 119.2 . . ?
C2 C3 H24 119.2 . . ?
C1 C2 C3 120.2(3) . . ?
C1 C2 H25 119.9 . . ?
C3 C2 H25 119.9 . . ?
C1 C6 C5 119.8(3) . . ?
C1 C6 H27 120.1 . . ?
C5 C6 H27 120.1 . . ?

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
C17 C12 C13 C14 -0.9(3) . . . . ?
N1 C12 C13 C14 -176.42(16) . . . . ?
C17 C12 C13 C9 174.68(18) . . . . ?
N1 C12 C13 C9 -0.84(18) . . . . ?
C12 C13 C14 C15 0.0(3) . . . . ?
C9 C13 C14 C15 -174.2(2) . . . . ?
C13 C12 C17 C16 1.4(3) . . . . ?
N1 C12 C17 C16 176.04(18) . . . . ?
C13 C14 C15 C16 0.3(3) . . . . ?
C14 C15 C16 C17 0.3(4) . . . . ?
C12 C17 C16 C15 -1.1(3) . . . . ?
C17 C12 N1 C10 170.73(19) . . . . ?
C13 C12 N1 C10 -14.20(18) . . . . ?
C17 C12 N1 S1 29.8(3) . . . . ?
C13 C12 N1 S1 -155.12(13) . . . . ?
O1 S1 N1 C12 -178.33(13) . . . . ?
O2 S1 N1 C12 -49.72(15) . . . . ?
C18 S1 N1 C12 66.88(15) . . . . ?
O1 S1 N1 C10 44.44(14) . . . . ?
O2 S1 N1 C10 173.04(12) . . . . ?
C18 S1 N1 C10 -70.36(14) . . . . ?
O1 S1 C18 C23 -18.01(19) . . . . ?
O2 S1 C18 C23 -149.75(16) . . . . ?
N1 S1 C18 C23 94.67(17) . . . . ?
O1 S1 C18 C19 162.34(16) . . . . ?
O2 S1 C18 C19 30.60(19) . . . . ?
N1 S1 C18 C19 -84.98(17) . . . . ?
C12 N1 C10 C9 22.58(17) . . . . ?
S1 N1 C10 C9 166.16(11) . . . . ?
C12 N1 C10 C11 136.56(16) . . . . ?
S1 N1 C10 C11 -79.87(19) . . . . ?
C14 C13 C9 C8 26.8(4) . . . . ?
C12 C13 C9 C8 -148.0(2) . . . . ?
C14 C13 C9 C10 -169.54(19) . . . . ?
C12 C13 C9 C10 15.72(19) . . . . ?
N1 C10 C9 C8 145.39(15) . . . . ?
C11 C10 C9 C8 20.0(2) . . . . ?
N1 C10 C9 C13 -23.36(18) . . . . ?
C11 C10 C9 C13 -148.70(15) . . . . ?
C13 C9 C8 C7 162.0(2) . . . . ?
C10 C9 C8 C7 -1.3(2) . . . . ?
C23 C18 C19 C20 -0.5(3) . . . . ?
S1 C18 C19 C20 179.19(17) . . . . ?
C9 C8 C7 C4 -140.14(18) . . . . ?
C9 C8 C7 C11 -17.4(2) . . . . ?
C18 C19 C20 C21 1.4(4) . . . . ?
C9 C10 C11 C7 -29.19(18) . . . . ?
N1 C10 C11 C7 -142.33(16) . . . . ?
C8 C7 C11 C10 28.11(19) . . . . ?
C4 C7 C11 C10 152.28(17) . . . . ?
C19 C18 C23 C22 -0.7(3) . . . . ?
S1 C18 C23 C22 179.68(17) . . . . ?
C19 C20 C21 C22 -1.2(4) . . . . ?
C19 C20 C21 C24 179.2(3) . . . . ?
C20 C21 C22 C23 0.0(4) . . . . ?
C24 C21 C22 C23 179.6(3) . . . . ?
C18 C23 C22 C21 0.9(4) . . . . ?
C8 C7 C4 C5 -140.5(2) . . . . ?
C11 C7 C4 C5 102.7(3) . . . . ?
C8 C7 C4 C3 43.4(3) . . . . ?
C11 C7 C4 C3 -73.4(3) . . . . ?
C3 C4 C5 C6 -1.8(4) . . . . ?
C7 C4 C5 C6 -178.0(3) . . . . ?
C5 C4 C3 C2 0.8(5) . . . . ?
C7 C4 C3 C2 177.1(4) . . . . ?
C6 C1 C2 C3 -3.5(7) . . . . ?
C4 C3 C2 C1 1.9(7) . . . . ?
C2 C1 C6 C5 2.5(6) . . . . ?
C4 C5 C6 C1 0.3(5) . . . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.264
_refine_diff_density_min         -0.265
_refine_diff_density_rms         0.049

####################################################################### 
# 
# 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_xxz20150420
_database_code_depnum_ccdc_archive 'CCDC 1414050'
_audit_update_record             
;
2015-07-21 deposited with the CCDC.
2015-12-24 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
1'-(Methylsulfonyl)-3-phenyl-2',3'-dihydro-1'H-spiro[indene-1,4'-quinoline]
_chemical_name_common            8y
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C24 H21 N O2 S'
_chemical_formula_weight         387.48

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/c

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

_cell_length_a                   14.001(3)
_cell_length_b                   12.335(2)
_cell_length_c                   11.587(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 95.497(5)
_cell_angle_gamma                90.00
_cell_volume                     1991.9(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       BLOCK
_exptl_crystal_colour            COLORLESS
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.15
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.292
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             816
_exptl_absorpt_coefficient_mu    0.182
_exptl_absorpt_correction_type   MULTI-SCAN
_exptl_absorpt_correction_T_min  0.9559
_exptl_absorpt_correction_T_max  0.9732
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            10857
_diffrn_reflns_av_R_equivalents  0.0662
_diffrn_reflns_av_sigmaI/netI    0.0732
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         2.20
_diffrn_reflns_theta_max         25.00
_reflns_number_total             3492
_reflns_number_gt                2019
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.0588P)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     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3492
_refine_ls_number_parameters     254
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1133
_refine_ls_R_factor_gt           0.0537
_refine_ls_wR_factor_ref         0.1325
_refine_ls_wR_factor_gt          0.1144
_refine_ls_goodness_of_fit_ref   0.992
_refine_ls_restrained_S_all      0.992
_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 -0.01569(5) 0.39646(8) 0.31080(11) 0.0918(4) Uani 1 1 d . . .
O2 O -0.05472(15) 0.3686(2) 0.4161(3) 0.1295(11) Uani 1 1 d . . .
O1 O -0.05743(15) 0.4836(2) 0.2437(3) 0.1432(12) Uani 1 1 d . . .
N1 N 0.09787(13) 0.42450(17) 0.3440(2) 0.0579(6) Uani 1 1 d . . .
C6 C 0.54529(15) 0.29483(18) 0.4830(2) 0.0391(6) Uani 1 1 d . . .
C1 C 0.62250(16) 0.2661(2) 0.4231(3) 0.0534(7) Uani 1 1 d . . .
H25 H 0.6115 0.2326 0.3511 0.064 Uiso 1 1 calc R . .
C2 C 0.71604(17) 0.2865(2) 0.4691(3) 0.0634(8) Uani 1 1 d . . .
H26 H 0.7671 0.2671 0.4277 0.076 Uiso 1 1 calc R . .
C3 C 0.7332(2) 0.3353(2) 0.5754(3) 0.0655(9) Uani 1 1 d . . .
H27 H 0.7958 0.3495 0.6060 0.079 Uiso 1 1 calc R . .
C4 C 0.6578(2) 0.3630(2) 0.6361(3) 0.0641(8) Uani 1 1 d . . .
H28 H 0.6695 0.3953 0.7086 0.077 Uiso 1 1 calc R . .
C5 C 0.56349(18) 0.3436(2) 0.5906(2) 0.0533(7) Uani 1 1 d . . .
H29 H 0.5128 0.3633 0.6325 0.064 Uiso 1 1 calc R . .
C7 C 0.44553(15) 0.27670(18) 0.4311(2) 0.0396(6) Uani 1 1 d . . .
C15 C 0.37256(15) 0.34639(18) 0.4310(2) 0.0430(6) Uani 1 1 d . . .
H31 H 0.3774 0.4141 0.4663 0.052 Uiso 1 1 calc R . .
C14 C 0.28064(15) 0.30275(18) 0.3667(2) 0.0416(6) Uani 1 1 d . . .
C13 C 0.31506(15) 0.19218(17) 0.3288(2) 0.0389(6) Uani 1 1 d . . .
C8 C 0.41169(15) 0.17794(17) 0.3691(2) 0.0392(6) Uani 1 1 d . . .
C9 C 0.45647(16) 0.07902(19) 0.3523(2) 0.0474(7) Uani 1 1 d . . .
H35 H 0.5203 0.0681 0.3801 0.057 Uiso 1 1 calc R . .
C10 C 0.40449(19) -0.0028(2) 0.2933(3) 0.0584(8) Uani 1 1 d . . .
H36 H 0.4339 -0.0689 0.2812 0.070 Uiso 1 1 calc R . .
C11 C 0.30962(19) 0.0127(2) 0.2524(3) 0.0605(8) Uani 1 1 d . . .
H37 H 0.2759 -0.0429 0.2124 0.073 Uiso 1 1 calc R . .
C12 C 0.26399(17) 0.11050(19) 0.2703(2) 0.0504(7) Uani 1 1 d . . .
H38 H 0.1999 0.1206 0.2431 0.060 Uiso 1 1 calc R . .
C22 C 0.20002(18) 0.2885(2) 0.4484(3) 0.0588(8) Uani 1 1 d . . .
H39A H 0.1566 0.2317 0.4186 0.071 Uiso 1 1 calc R . .
H39B H 0.2281 0.2668 0.5247 0.071 Uiso 1 1 calc R . .
C23 C 0.14495(18) 0.3919(2) 0.4583(3) 0.0622(8) Uani 1 1 d . . .
H40A H 0.0968 0.3818 0.5122 0.075 Uiso 1 1 calc R . .
H40B H 0.1882 0.4488 0.4883 0.075 Uiso 1 1 calc R . .
C21 C 0.16093(16) 0.43172(19) 0.2535(2) 0.0459(7) Uani 1 1 d . . .
C16 C 0.24816(14) 0.37611(17) 0.2635(2) 0.0375(6) Uani 1 1 d . . .
C17 C 0.30915(16) 0.39219(19) 0.1773(2) 0.0463(7) Uani 1 1 d . . .
H43 H 0.3684 0.3575 0.1839 0.056 Uiso 1 1 calc R . .
C18 C 0.2855(2) 0.4571(2) 0.0829(2) 0.0559(7) Uani 1 1 d . . .
H44 H 0.3280 0.4659 0.0266 0.067 Uiso 1 1 calc R . .
C19 C 0.1985(2) 0.5092(2) 0.0725(3) 0.0637(8) Uani 1 1 d . . .
H45 H 0.1812 0.5521 0.0079 0.076 Uiso 1 1 calc R . .
C20 C 0.1371(2) 0.4980(2) 0.1566(3) 0.0637(8) Uani 1 1 d . . .
H46 H 0.0789 0.5349 0.1496 0.076 Uiso 1 1 calc R . .
C24 C -0.0188(3) 0.2826(4) 0.2216(5) 0.1447(19) Uani 1 1 d . . .
H52A H -0.0835 0.2698 0.1892 0.217 Uiso 1 1 calc R . .
H52B H 0.0040 0.2207 0.2663 0.217 Uiso 1 1 calc R . .
H52C H 0.0214 0.2945 0.1602 0.217 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
S1 O1 1.419(3) . ?
S1 O2 1.426(3) . ?
S1 N1 1.637(2) . ?
S1 C24 1.742(4) . ?
N1 C21 1.437(3) . ?
N1 C23 1.477(4) . ?
C6 C1 1.385(3) . ?
C6 C5 1.386(3) . ?
C6 C7 1.483(3) . ?
C1 C2 1.389(3) . ?
C2 C3 1.371(4) . ?
C3 C4 1.367(4) . ?
C4 C5 1.395(3) . ?
C7 C15 1.335(3) . ?
C7 C8 1.470(3) . ?
C15 C14 1.523(3) . ?
C14 C13 1.525(3) . ?
C14 C16 1.533(3) . ?
C14 C22 1.551(3) . ?
C13 C12 1.376(3) . ?
C13 C8 1.399(3) . ?
C8 C9 1.394(3) . ?
C9 C10 1.385(3) . ?
C10 C11 1.380(4) . ?
C11 C12 1.390(3) . ?
C22 C23 1.500(3) . ?
C21 C16 1.396(3) . ?
C21 C20 1.403(4) . ?
C16 C17 1.389(3) . ?
C17 C18 1.371(3) . ?
C18 C19 1.372(4) . ?
C19 C20 1.367(4) . ?

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
O1 S1 O2 118.67(17) . . ?
O1 S1 N1 107.97(15) . . ?
O2 S1 N1 107.03(15) . . ?
O1 S1 C24 107.4(2) . . ?
O2 S1 C24 108.9(2) . . ?
N1 S1 C24 106.18(15) . . ?
C21 N1 C23 114.73(19) . . ?
C21 N1 S1 119.50(19) . . ?
C23 N1 S1 119.57(19) . . ?
C1 C6 C5 118.5(2) . . ?
C1 C6 C7 120.6(2) . . ?
C5 C6 C7 121.0(2) . . ?
C6 C1 C2 120.9(3) . . ?
C3 C2 C1 120.1(3) . . ?
C4 C3 C2 119.6(3) . . ?
C3 C4 C5 120.8(3) . . ?
C6 C5 C4 120.0(3) . . ?
C15 C7 C8 108.8(2) . . ?
C15 C7 C6 126.4(2) . . ?
C8 C7 C6 124.74(19) . . ?
C7 C15 C14 112.6(2) . . ?
C15 C14 C13 100.46(17) . . ?
C15 C14 C16 110.29(18) . . ?
C13 C14 C16 112.4(2) . . ?
C15 C14 C22 111.8(2) . . ?
C13 C14 C22 110.08(19) . . ?
C16 C14 C22 111.34(18) . . ?
C12 C13 C8 120.9(2) . . ?
C12 C13 C14 129.3(2) . . ?
C8 C13 C14 109.76(19) . . ?
C9 C8 C13 119.8(2) . . ?
C9 C8 C7 131.7(2) . . ?
C13 C8 C7 108.39(18) . . ?
C10 C9 C8 119.0(2) . . ?
C11 C10 C9 120.8(2) . . ?
C10 C11 C12 120.6(2) . . ?
C13 C12 C11 119.0(2) . . ?
C23 C22 C14 111.1(2) . . ?
N1 C23 C22 110.6(2) . . ?
C16 C21 C20 119.4(2) . . ?
C16 C21 N1 120.2(2) . . ?
C20 C21 N1 120.3(2) . . ?
C17 C16 C21 117.6(2) . . ?
C17 C16 C14 119.21(19) . . ?
C21 C16 C14 123.1(2) . . ?
C18 C17 C16 122.6(2) . . ?
C17 C18 C19 119.2(3) . . ?
C20 C19 C18 120.2(3) . . ?
C19 C20 C21 120.8(3) . . ?

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
O1 S1 N1 C21 -65.0(2) . . . . ?
O2 S1 N1 C21 166.14(19) . . . . ?
C24 S1 N1 C21 49.9(3) . . . . ?
O1 S1 N1 C23 144.1(2) . . . . ?
O2 S1 N1 C23 15.3(2) . . . . ?
C24 S1 N1 C23 -100.9(3) . . . . ?
C5 C6 C1 C2 -0.7(4) . . . . ?
C7 C6 C1 C2 177.5(2) . . . . ?
C6 C1 C2 C3 0.3(4) . . . . ?
C1 C2 C3 C4 0.4(4) . . . . ?
C2 C3 C4 C5 -0.8(4) . . . . ?
C1 C6 C5 C4 0.3(4) . . . . ?
C7 C6 C5 C4 -177.9(2) . . . . ?
C3 C4 C5 C6 0.5(4) . . . . ?
C1 C6 C7 C15 -135.7(3) . . . . ?
C5 C6 C7 C15 42.4(4) . . . . ?
C1 C6 C7 C8 43.2(3) . . . . ?
C5 C6 C7 C8 -138.7(2) . . . . ?
C8 C7 C15 C14 -0.9(3) . . . . ?
C6 C7 C15 C14 178.2(2) . . . . ?
C7 C15 C14 C13 0.0(3) . . . . ?
C7 C15 C14 C16 -118.8(2) . . . . ?
C7 C15 C14 C22 116.7(2) . . . . ?
C15 C14 C13 C12 177.1(2) . . . . ?
C16 C14 C13 C12 -65.7(3) . . . . ?
C22 C14 C13 C12 59.1(3) . . . . ?
C15 C14 C13 C8 0.9(2) . . . . ?
C16 C14 C13 C8 118.2(2) . . . . ?
C22 C14 C13 C8 -117.1(2) . . . . ?
C12 C13 C8 C9 -1.4(4) . . . . ?
C14 C13 C8 C9 175.1(2) . . . . ?
C12 C13 C8 C7 -178.0(2) . . . . ?
C14 C13 C8 C7 -1.5(3) . . . . ?
C15 C7 C8 C9 -174.6(3) . . . . ?
C6 C7 C8 C9 6.4(4) . . . . ?
C15 C7 C8 C13 1.5(3) . . . . ?
C6 C7 C8 C13 -177.6(2) . . . . ?
C13 C8 C9 C10 1.4(4) . . . . ?
C7 C8 C9 C10 177.0(2) . . . . ?
C8 C9 C10 C11 -0.4(4) . . . . ?
C9 C10 C11 C12 -0.5(4) . . . . ?
C8 C13 C12 C11 0.5(4) . . . . ?
C14 C13 C12 C11 -175.3(2) . . . . ?
C10 C11 C12 C13 0.5(4) . . . . ?
C15 C14 C22 C23 86.4(3) . . . . ?
C13 C14 C22 C23 -162.9(2) . . . . ?
C16 C14 C22 C23 -37.5(3) . . . . ?
C21 N1 C23 C22 -53.4(3) . . . . ?
S1 N1 C23 C22 98.7(2) . . . . ?
C14 C22 C23 N1 61.5(3) . . . . ?
C23 N1 C21 C16 21.5(3) . . . . ?
S1 N1 C21 C16 -130.7(2) . . . . ?
C23 N1 C21 C20 -156.0(2) . . . . ?
S1 N1 C21 C20 51.8(3) . . . . ?
C20 C21 C16 C17 1.9(3) . . . . ?
N1 C21 C16 C17 -175.5(2) . . . . ?
C20 C21 C16 C14 179.4(2) . . . . ?
N1 C21 C16 C14 1.9(3) . . . . ?
C15 C14 C16 C17 59.4(3) . . . . ?
C13 C14 C16 C17 -51.8(3) . . . . ?
C22 C14 C16 C17 -175.9(2) . . . . ?
C15 C14 C16 C21 -118.0(2) . . . . ?
C13 C14 C16 C21 130.7(2) . . . . ?
C22 C14 C16 C21 6.7(3) . . . . ?
C21 C16 C17 C18 -2.0(3) . . . . ?
C14 C16 C17 C18 -179.5(2) . . . . ?
C16 C17 C18 C19 0.3(4) . . . . ?
C17 C18 C19 C20 1.4(4) . . . . ?
C18 C19 C20 C21 -1.4(4) . . . . ?
C16 C21 C20 C19 -0.3(4) . . . . ?
N1 C21 C20 C19 177.2(2) . . . . ?

_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.996
_refine_diff_density_max         0.219
_refine_diff_density_min         -0.325
_refine_diff_density_rms         0.045

####################################################################### 
# 
# 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_wzm2012042013
_database_code_depnum_ccdc_archive 'CCDC 1414065'
_audit_update_record             
;
2015-07-21 deposited with the CCDC.
2015-12-24 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
2-Phenyl-4-tosyl-1,2,3,4-tetrahydrocyclopenta[b]indole
_chemical_name_common            6a
_chemical_melting_point          ?
_chemical_formula_moiety         'C24 H21 N O2 S'
_chemical_formula_sum            'C24 H21 N O2 S'
_chemical_formula_weight         387.48

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/C
_symmetry_space_group_name_Hall  '-P 2ybc '

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

_cell_length_a                   8.9249(10)
_cell_length_b                   9.9995(10)
_cell_length_c                   22.9440(19)
_cell_angle_alpha                90.00
_cell_angle_beta                 107.130(4)
_cell_angle_gamma                90.00
_cell_volume                     1956.8(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    4433
_cell_measurement_theta_min      2.76
_cell_measurement_theta_max      26.51

_exptl_crystal_description       BLOCK
_exptl_crystal_colour            COLORLESS
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.15
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.315
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             816
_exptl_absorpt_coefficient_mu    0.185
_exptl_absorpt_correction_type   MULTI-SCAN
_exptl_absorpt_correction_T_min  0.9639
_exptl_absorpt_correction_T_max  0.9728
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            10795
_diffrn_reflns_av_R_equivalents  0.0257
_diffrn_reflns_av_sigmaI/netI    0.0304
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         1.86
_diffrn_reflns_theta_max         25.50
_reflns_number_total             3603
_reflns_number_gt                2853
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.0706P)²+0.4346P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    CONSTR
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3603
_refine_ls_number_parameters     254
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0577
_refine_ls_R_factor_gt           0.0446
_refine_ls_wR_factor_ref         0.1309
_refine_ls_wR_factor_gt          0.1237
_refine_ls_goodness_of_fit_ref   1.006
_refine_ls_restrained_S_all      1.006
_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 0.41167(6) 0.19953(6) 0.10933(2) 0.0666(2) Uani 1 1 d . . .
O1 O 0.3756(2) 0.33439(17) 0.09148(7) 0.0904(5) Uani 1 1 d . . .
O2 O 0.29141(15) 0.10133(19) 0.09750(7) 0.0838(5) Uani 1 1 d . . .
N1 N 0.53821(17) 0.14825(17) 0.07307(7) 0.0588(4) Uani 1 1 d . . .
C1 C 0.7852(3) 0.1632(3) 0.37485(10) 0.0918(7) Uani 1 1 d . . .
H1A H 0.7310 0.1069 0.3959 0.138 Uiso 1 1 calc R . .
H1B H 0.7988 0.2506 0.3930 0.138 Uiso 1 1 calc R . .
H1C H 0.8860 0.1253 0.3778 0.138 Uiso 1 1 calc R . .
C2 C 0.6910(2) 0.1742(2) 0.30884(9) 0.0628(5) Uani 1 1 d . . .
C3 C 0.5606(3) 0.0958(2) 0.28531(10) 0.0710(6) Uani 1 1 d . . .
H3 H 0.5300 0.0364 0.3108 0.085 Uiso 1 1 calc R . .
C4 C 0.4740(2) 0.1032(2) 0.22465(10) 0.0676(5) Uani 1 1 d . . .
H4 H 0.3866 0.0489 0.2095 0.081 Uiso 1 1 calc R . .
C5 C 0.5183(2) 0.19168(19) 0.18684(8) 0.0554(4) Uani 1 1 d . . .
C6 C 0.6486(3) 0.2710(2) 0.20944(9) 0.0702(6) Uani 1 1 d . . .
H6 H 0.6787 0.3311 0.1840 0.084 Uiso 1 1 calc R . .
C7 C 0.7337(3) 0.2608(2) 0.26984(10) 0.0743(6) Uani 1 1 d . . .
H7 H 0.8224 0.3138 0.2848 0.089 Uiso 1 1 calc R . .
C8 C 0.6563(2) 0.2293(2) 0.06014(8) 0.0604(5) Uani 1 1 d . . .
C9 C 0.6585(3) 0.3647(3) 0.04871(10) 0.0801(6) Uani 1 1 d . . .
H9 H 0.5753 0.4199 0.0496 0.096 Uiso 1 1 calc R . .
C10 C 0.7899(4) 0.4148(3) 0.03590(11) 0.0978(9) Uani 1 1 d . . .
H10 H 0.7952 0.5059 0.0285 0.117 Uiso 1 1 calc R . .
C11 C 0.9133(4) 0.3337(4) 0.03375(11) 0.1009(9) Uani 1 1 d . . .
H11 H 1.0003 0.3711 0.0255 0.121 Uiso 1 1 calc R . .
C12 C 0.9094(3) 0.1988(3) 0.04367(9) 0.0833(7) Uani 1 1 d . . .
H12 H 0.9920 0.1443 0.0414 0.100 Uiso 1 1 calc R . .
C13 C 0.7790(2) 0.1440(2) 0.05721(8) 0.0629(5) Uani 1 1 d . . .
C14 C 0.7366(2) 0.0116(2) 0.07085(8) 0.0614(5) Uani 1 1 d . . .
C15 C 0.5975(2) 0.0170(2) 0.08118(8) 0.0557(5) Uani 1 1 d . . .
C17 C 0.5350(2) -0.1129(2) 0.09446(9) 0.0662(5) Uani 1 1 d . . .
H17A H 0.4468 -0.1420 0.0609 0.079 Uiso 1 1 calc R . .
H17B H 0.5036 -0.1089 0.1315 0.079 Uiso 1 1 calc R . .
C18 C 0.6804(3) -0.2055(2) 0.10240(9) 0.0701(6) Uani 1 1 d . . .
H18 H 0.6464 -0.2875 0.0788 0.084 Uiso 1 1 calc R . .
C19 C 0.7952(3) -0.1288(3) 0.07462(10) 0.0807(7) Uani 1 1 d . . .
H19A H 0.9023 -0.1350 0.1009 0.097 Uiso 1 1 calc R . .
H19B H 0.7902 -0.1632 0.0346 0.097 Uiso 1 1 calc R . .
C20 C 0.7602(2) -0.24315(19) 0.16833(9) 0.0588(5) Uani 1 1 d . . .
C21 C 0.7724(3) -0.1554(2) 0.21576(9) 0.0674(5) Uani 1 1 d . . .
H21 H 0.7267 -0.0712 0.2076 0.081 Uiso 1 1 calc R . .
C22 C 0.8510(3) -0.1899(3) 0.27492(10) 0.0781(6) Uani 1 1 d . . .
H22 H 0.8574 -0.1291 0.3063 0.094 Uiso 1 1 calc R . .
C23 C 0.9193(3) -0.3124(3) 0.28792(11) 0.0860(7) Uani 1 1 d . . .
H23 H 0.9729 -0.3352 0.3279 0.103 Uiso 1 1 calc R . .
C24 C 0.9083(3) -0.4017(3) 0.24158(13) 0.0865(7) Uani 1 1 d . . .
H24 H 0.9545 -0.4857 0.2501 0.104 Uiso 1 1 calc R . .
C25 C 0.8289(3) -0.3674(2) 0.18222(11) 0.0719(6) Uani 1 1 d . . .
H25 H 0.8216 -0.4289 0.1511 0.086 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
S1 O1 1.4185(17) . ?
S1 O2 1.4207(17) . ?
S1 N1 1.6684(15) . ?
S1 C5 1.7543(19) . ?
N1 C15 1.406(2) . ?
N1 C8 1.428(3) . ?
C1 C2 1.504(3) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C2 C3 1.375(3) . ?
C2 C7 1.377(3) . ?
C3 C4 1.381(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.376(3) . ?
C4 H4 0.9300 . ?
C5 C6 1.377(3) . ?
C6 C7 1.374(3) . ?
C6 H6 0.9300 . ?
C7 H7 0.9300 . ?
C8 C9 1.381(3) . ?
C8 C13 1.405(3) . ?
C9 C10 1.384(4) . ?
C9 H9 0.9300 . ?
C10 C11 1.381(4) . ?
C10 H10 0.9300 . ?
C11 C12 1.371(4) . ?
C11 H11 0.9300 . ?
C12 C13 1.401(3) . ?
C12 H12 0.9300 . ?
C13 C14 1.437(3) . ?
C14 C15 1.333(3) . ?
C14 C19 1.491(3) . ?
C15 C17 1.480(3) . ?
C17 C18 1.560(3) . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C18 C20 1.517(3) . ?
C18 C19 1.558(3) . ?
C18 H18 0.9800 . ?
C19 H19A 0.9700 . ?
C19 H19B 0.9700 . ?
C20 C21 1.377(3) . ?
C20 C25 1.380(3) . ?
C21 C22 1.375(3) . ?
C21 H21 0.9300 . ?
C22 C23 1.362(4) . ?
C22 H22 0.9300 . ?
C23 C24 1.370(4) . ?
C23 H23 0.9300 . ?
C24 C25 1.381(3) . ?
C24 H24 0.9300 . ?
C25 H25 0.9300 . ?

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
O1 S1 O2 120.50(10) . . ?
O1 S1 N1 106.11(10) . . ?
O2 S1 N1 106.06(9) . . ?
O1 S1 C5 110.15(10) . . ?
O2 S1 C5 108.45(10) . . ?
N1 S1 C5 104.29(8) . . ?
C15 N1 C8 106.55(15) . . ?
C15 N1 S1 120.27(14) . . ?
C8 N1 S1 125.35(14) . . ?
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C3 C2 C7 117.88(19) . . ?
C3 C2 C1 120.8(2) . . ?
C7 C2 C1 121.4(2) . . ?
C2 C3 C4 121.52(19) . . ?
C2 C3 H3 119.2 . . ?
C4 C3 H3 119.2 . . ?
C5 C4 C3 119.40(19) . . ?
C5 C4 H4 120.3 . . ?
C3 C4 H4 120.3 . . ?
C4 C5 C6 120.04(19) . . ?
C4 C5 S1 119.81(16) . . ?
C6 C5 S1 120.13(15) . . ?
C7 C6 C5 119.46(19) . . ?
C7 C6 H6 120.3 . . ?
C5 C6 H6 120.3 . . ?
C6 C7 C2 121.7(2) . . ?
C6 C7 H7 119.1 . . ?
C2 C7 H7 119.1 . . ?
C9 C8 C13 122.0(2) . . ?
C9 C8 N1 130.45(19) . . ?
C13 C8 N1 107.43(18) . . ?
C8 C9 C10 117.1(2) . . ?
C8 C9 H9 121.4 . . ?
C10 C9 H9 121.4 . . ?
C11 C10 C9 122.0(3) . . ?
C11 C10 H10 119.0 . . ?
C9 C10 H10 119.0 . . ?
C12 C11 C10 120.9(3) . . ?
C12 C11 H11 119.6 . . ?
C10 C11 H11 119.6 . . ?
C11 C12 C13 119.0(2) . . ?
C11 C12 H12 120.5 . . ?
C13 C12 H12 120.5 . . ?
C12 C13 C8 118.9(2) . . ?
C12 C13 C14 134.2(2) . . ?
C8 C13 C14 106.84(17) . . ?
C15 C14 C13 108.65(17) . . ?
C15 C14 C19 110.9(2) . . ?
C13 C14 C19 140.36(18) . . ?
C14 C15 N1 110.40(18) . . ?
C14 C15 C17 115.33(18) . . ?
N1 C15 C17 134.14(17) . . ?
C15 C17 C18 101.20(16) . . ?
C15 C17 H17A 111.5 . . ?
C18 C17 H17A 111.5 . . ?
C15 C17 H17B 111.5 . . ?
C18 C17 H17B 111.5 . . ?
H17A C17 H17B 109.3 . . ?
C20 C18 C19 110.96(17) . . ?
C20 C18 C17 113.18(17) . . ?
C19 C18 C17 106.52(17) . . ?
C20 C18 H18 108.7 . . ?
C19 C18 H18 108.7 . . ?
C17 C18 H18 108.7 . . ?
C14 C19 C18 103.06(16) . . ?
C14 C19 H19A 111.2 . . ?
C18 C19 H19A 111.2 . . ?
C14 C19 H19B 111.2 . . ?
C18 C19 H19B 111.2 . . ?
H19A C19 H19B 109.1 . . ?
C21 C20 C25 117.68(19) . . ?
C21 C20 C18 122.30(17) . . ?
C25 C20 C18 119.98(18) . . ?
C22 C21 C20 121.3(2) . . ?
C22 C21 H21 119.4 . . ?
C20 C21 H21 119.4 . . ?
C23 C22 C21 120.4(2) . . ?
C23 C22 H22 119.8 . . ?
C21 C22 H22 119.8 . . ?
C22 C23 C24 119.5(2) . . ?
C22 C23 H23 120.3 . . ?
C24 C23 H23 120.3 . . ?
C23 C24 C25 120.1(2) . . ?
C23 C24 H24 119.9 . . ?
C25 C24 H24 119.9 . . ?
C20 C25 C24 121.1(2) . . ?
C20 C25 H25 119.5 . . ?
C24 C25 H25 119.5 . . ?

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
O1 S1 N1 C15 -179.98(14) . . . . ?
O2 S1 N1 C15 -50.72(15) . . . . ?
C5 S1 N1 C15 63.69(15) . . . . ?
O1 S1 N1 C8 35.07(16) . . . . ?
O2 S1 N1 C8 164.33(14) . . . . ?
C5 S1 N1 C8 -81.26(15) . . . . ?
C7 C2 C3 C4 -0.2(3) . . . . ?
C1 C2 C3 C4 -179.1(2) . . . . ?
C2 C3 C4 C5 -0.5(3) . . . . ?
C3 C4 C5 C6 0.5(3) . . . . ?
C3 C4 C5 S1 178.66(15) . . . . ?
O1 S1 C5 C4 131.45(17) . . . . ?
O2 S1 C5 C4 -2.37(18) . . . . ?
N1 S1 C5 C4 -115.07(16) . . . . ?
O1 S1 C5 C6 -50.41(19) . . . . ?
O2 S1 C5 C6 175.77(16) . . . . ?
N1 S1 C5 C6 63.07(18) . . . . ?
C4 C5 C6 C7 0.1(3) . . . . ?
S1 C5 C6 C7 -178.01(17) . . . . ?
C5 C6 C7 C2 -0.8(4) . . . . ?
C3 C2 C7 C6 0.9(3) . . . . ?
C1 C2 C7 C6 179.8(2) . . . . ?
C15 N1 C8 C9 -179.79(19) . . . . ?
S1 N1 C8 C9 -30.9(3) . . . . ?
C15 N1 C8 C13 3.43(18) . . . . ?
S1 N1 C8 C13 152.27(13) . . . . ?
C13 C8 C9 C10 -1.9(3) . . . . ?
N1 C8 C9 C10 -178.30(19) . . . . ?
C8 C9 C10 C11 0.8(3) . . . . ?
C9 C10 C11 C12 0.7(4) . . . . ?
C10 C11 C12 C13 -1.2(4) . . . . ?
C11 C12 C13 C8 0.1(3) . . . . ?
C11 C12 C13 C14 -178.8(2) . . . . ?
C9 C8 C13 C12 1.5(3) . . . . ?
N1 C8 C13 C12 178.64(16) . . . . ?
C9 C8 C13 C14 -179.32(17) . . . . ?
N1 C8 C13 C14 -2.20(18) . . . . ?
C12 C13 C14 C15 179.1(2) . . . . ?
C8 C13 C14 C15 0.1(2) . . . . ?
C12 C13 C14 C19 -4.2(4) . . . . ?
C8 C13 C14 C19 176.9(2) . . . . ?
C13 C14 C15 N1 2.1(2) . . . . ?
C19 C14 C15 N1 -175.66(15) . . . . ?
C13 C14 C15 C17 178.52(15) . . . . ?
C19 C14 C15 C17 0.7(2) . . . . ?
C8 N1 C15 C14 -3.48(19) . . . . ?
S1 N1 C15 C14 -154.23(13) . . . . ?
C8 N1 C15 C17 -178.93(19) . . . . ?
S1 N1 C15 C17 30.3(3) . . . . ?
C14 C15 C17 C18 9.9(2) . . . . ?
N1 C15 C17 C18 -174.77(18) . . . . ?
C15 C17 C18 C20 106.22(19) . . . . ?
C15 C17 C18 C19 -15.99(19) . . . . ?
C15 C14 C19 C18 -11.1(2) . . . . ?
C13 C14 C19 C18 172.1(2) . . . . ?
C20 C18 C19 C14 -106.89(18) . . . . ?
C17 C18 C19 C14 16.7(2) . . . . ?
C19 C18 C20 C21 83.4(2) . . . . ?
C17 C18 C20 C21 -36.2(3) . . . . ?
C19 C18 C20 C25 -94.1(2) . . . . ?
C17 C18 C20 C25 146.20(19) . . . . ?
C25 C20 C21 C22 0.3(3) . . . . ?
C18 C20 C21 C22 -177.3(2) . . . . ?
C20 C21 C22 C23 0.2(4) . . . . ?
C21 C22 C23 C24 -0.4(4) . . . . ?
C22 C23 C24 C25 0.1(4) . . . . ?
C21 C20 C25 C24 -0.6(3) . . . . ?
C18 C20 C25 C24 177.0(2) . . . . ?
C23 C24 C25 C20 0.4(4) . . . . ?

_diffrn_measured_fraction_theta_max 0.989
_diffrn_reflns_theta_full        25.50
_diffrn_measured_fraction_theta_full 0.989
_refine_diff_density_max         0.165
_refine_diff_density_min         -0.235
_refine_diff_density_rms         0.030
