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

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

data_wcm-170401
_database_code_depnum_ccdc_archive 'CCDC 1569442'
_audit_update_record             
;
2017-08-17 deposited with the CCDC.
2018-06-18 downloaded from the CCDC.
;
_audit_creation_date             2017-04-16
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.03.02 svn.r3394 for OlexSys, GUI svn.r5324)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        
(3S,10aS)-1-((4-bromophenyl)sulfonyl)-7-methyl-3,4-diphenyl-9-tosyl-3,9,10,10a-tetrahydropyrrolo[2,3-b]carbazol-2(1H)-one
_chemical_formula_moiety         'C40 H31 Br N2 O5 S2'
_chemical_formula_sum            'C42 H36 Br Cl2 N2 O5.50 S2'
_chemical_formula_weight         871.66
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.6763 1.2805 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   10.1352(5)
_cell_length_b                   13.2429(7)
_cell_length_c                   16.5954(8)
_cell_angle_alpha                110.962(5)
_cell_angle_beta                 96.295(4)
_cell_angle_gamma                91.276(4)
_cell_volume                     2062.93(19)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    4686
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      64.0020
_cell_measurement_theta_min      3.6830
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    3.882
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.38907
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            white
_exptl_crystal_density_diffrn    1.403
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_F_000             894
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.2000
_diffrn_reflns_av_unetI/netI     0.1484
_diffrn_reflns_Laue_measured_fraction_full 0.948
_diffrn_reflns_Laue_measured_fraction_max 0.948
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            19767
_diffrn_reflns_point_group_measured_fraction_full 0.948
_diffrn_reflns_point_group_measured_fraction_max 0.948
_diffrn_reflns_theta_full        61.160
_diffrn_reflns_theta_max         61.160
_diffrn_reflns_theta_min         3.582
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.4741
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.948
_diffrn_measured_fraction_theta_max 0.948
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega -115.00  -11.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.5672  -57.0000  -90.0000 104

#__ type_ start__ end____ width___ exp.time_
  2 omega -119.00   -7.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.5672  -77.0000 -120.0000 112

#__ type_ start__ end____ width___ exp.time_
  3 omega -119.00   -7.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.5672  -77.0000   30.0000 112

#__ type_ start__ end____ width___ exp.time_
  4 omega -119.00   -7.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.5672  -77.0000  -30.0000 112

#__ type_ start__ end____ width___ exp.time_
  5 omega -119.00   -7.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.5672  -77.0000 -150.0000 112

#__ type_ start__ end____ width___ exp.time_
  6 omega  -96.00   -2.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.5672  125.0000  -30.0000 94

#__ type_ start__ end____ width___ exp.time_
  7 omega -119.00   -7.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.5672  -77.0000  120.0000 112

#__ type_ start__ end____ width___ exp.time_
  8 omega   23.00   98.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       40.5672 -125.0000 -120.0000 75

#__ type_ start__ end____ width___ exp.time_
  9 omega   59.00  167.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       91.1609   69.0000  -41.8642 108

#__ type_ start__ end____ width___ exp.time_
 10 omega    7.00  109.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       91.1609  -94.0000  120.0000 102

#__ type_ start__ end____ width___ exp.time_
 11 omega    7.00  109.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       91.1609  -94.0000 -120.0000 102

#__ type_ start__ end____ width___ exp.time_
 12 omega   58.00  170.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       91.1609   77.0000 -120.0000 112

#__ type_ start__ end____ width___ exp.time_
 13 omega   58.00  169.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       91.1609   75.0000   39.2826 111

#__ type_ start__ end____ width___ exp.time_
 14 omega   58.00  169.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       91.1609   76.0000 -159.6954 111

#__ type_ start__ end____ width___ exp.time_
 15 omega   94.00  166.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       91.1609  125.0000   60.0000 72

#__ type_ start__ end____ width___ exp.time_
 16 omega   58.00  170.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       91.1609   77.0000 -180.0000 112

#__ type_ start__ end____ width___ exp.time_
 17 omega   58.00  169.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       91.1609   74.0000   76.4023 111

#__ type_ start__ end____ width___ exp.time_
 18 omega   58.00   83.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       91.1609   77.0000  -90.0000 25
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.1483619000
_diffrn_orient_matrix_UB_12      -0.0096793000
_diffrn_orient_matrix_UB_13      0.0263621000
_diffrn_orient_matrix_UB_21      -0.0321036000
_diffrn_orient_matrix_UB_22      -0.0023015000
_diffrn_orient_matrix_UB_23      0.0879633000
_diffrn_orient_matrix_UB_31      -0.0211318000
_diffrn_orient_matrix_UB_32      -0.1244531000
_diffrn_orient_matrix_UB_33      -0.0401158000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3528
_reflns_number_total             6019
_reflns_odcompleteness_completeness 94.80
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     61.08
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    ?
_refine_diff_density_max         4.872
_refine_diff_density_min         -0.561
_refine_diff_density_rms         0.281
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.981
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     453
_refine_ls_number_reflns         6019
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.2899
_refine_ls_R_factor_gt           0.1978
_refine_ls_restrained_S_all      1.981
_refine_ls_shift/su_max          0.251
_refine_ls_shift/su_mean         0.035
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1504P)²+3.5839P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.4901
_refine_ls_wR_factor_ref         0.5161
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C00E(H00E), C00I(H00I)
2.b Secondary CH2 refined with riding coordinates:
 C00P(H00A,H00B)
2.c Aromatic/amide H refined with riding coordinates:
 C00N(H00N), C00O(H00O), C00R(H00R), C00S(H00S), C00T(H00T), C00V(H00V),
 C00Y(H00Y), C00Z(H00Z), C010(H010), C011(H011), C012(H012), C013(H013),
 C015(H015), C018(H018), C019(H019), C01A(H01A), C01B(H01B), C01C(H01C),
 C01D(H01D), C01F(H01H), C1AA(H1AA)
2.d Idealised Me refined as rotating group:
 C01E(H01E,H01F,H01G), C01G(H01I,H01J,H01K)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br01 Br 1.1959(2) 0.8640(2) 0.07030(19) 0.1272(13) Uani 1 1 d . . . . .
S03 S 0.2398(4) 0.7333(3) 0.3917(2) 0.0558(11) Uani 1 1 d . . . . .
O004 O 0.6588(10) 0.5645(8) -0.0025(6) 0.056(3) Uani 1 1 d . . . . .
N005 N 0.5954(11) 0.6453(9) 0.1325(7) 0.048(3) Uani 1 1 d . . . . .
O006 O 0.2282(11) 0.7779(9) 0.3255(6) 0.065(3) Uani 1 1 d . . . . .
O007 O 0.5890(12) 0.8345(8) 0.2241(8) 0.074(3) Uani 1 1 d . . . . .
S008 S 0.6042(4) 0.7734(3) 0.1385(3) 0.0552(11) Uani 1 1 d . . . . .
N009 N 0.3000(11) 0.6125(9) 0.3497(7) 0.046(3) Uani 1 1 d . . . . .
O00A O 0.1227(10) 0.7152(9) 0.4267(7) 0.069(3) Uani 1 1 d . . . . .
C00C C 0.6348(13) 0.5601(11) 0.0653(9) 0.043(3) Uani 1 1 d . . . . .
C00D C 0.4410(12) 0.4886(11) 0.2797(8) 0.042(3) Uani 1 1 d . . . . .
C00E C 0.5576(13) 0.6171(10) 0.2067(8) 0.041(3) Uani 1 1 d . . . . .
H00E H 0.6183 0.6560 0.2597 0.049 Uiso 1 1 calc R . . . .
C00F C 0.3861(13) 0.5829(11) 0.2838(8) 0.042(3) Uani 1 1 d . . . . .
C00G C 0.5790(12) 0.4938(10) 0.1747(8) 0.036(3) Uani 1 1 d . . . . .
C00H C 0.3944(13) 0.4593(11) 0.3500(8) 0.044(3) Uani 1 1 d . . . . .
C00I C 0.6562(12) 0.4649(10) 0.0979(8) 0.041(3) Uani 1 1 d . . . . .
H00I H 0.6199 0.3961 0.0528 0.049 Uiso 1 1 calc R . . . .
C00J C 0.5208(12) 0.4330(10) 0.2096(8) 0.039(3) Uani 1 1 d . . . . .
C00K C 0.8064(13) 0.4633(11) 0.1199(9) 0.044(3) Uani 1 1 d . . . . .
C00L C 0.5229(13) 0.3136(11) 0.1806(8) 0.045(3) Uani 1 1 d . . . . .
C00M C 0.3107(13) 0.5369(11) 0.3912(9) 0.046(3) Uani 1 1 d . . . . .
C00N C 0.4278(16) 0.3757(12) 0.3804(10) 0.058(4) Uani 1 1 d . . . . .
H00N H 0.4886 0.3261 0.3552 0.070 Uiso 1 1 calc R . . . .
C00O C 0.4076(15) 0.2495(12) 0.1663(9) 0.057(4) Uani 1 1 d . . . . .
H00O H 0.3281 0.2827 0.1768 0.068 Uiso 1 1 calc R . . . .
C00P C 0.4153(13) 0.6384(11) 0.2227(9) 0.044(3) Uani 1 1 d . . . . .
H00A H 0.4050 0.7156 0.2486 0.053 Uiso 1 1 calc R . . . .
H00B H 0.3557 0.6089 0.1687 0.053 Uiso 1 1 calc R . . . .
C00Q C 0.7682(14) 0.7958(11) 0.1199(9) 0.049(3) Uani 1 1 d . . . . .
C00R C 0.8802(15) 0.4230(13) 0.0514(10) 0.061(4) Uani 1 1 d . . . . .
H00R H 0.8396 0.3962 -0.0059 0.074 Uiso 1 1 calc R . . . .
C00S C 0.3668(17) 0.3703(14) 0.4493(10) 0.065(4) Uani 1 1 d . . . . .
H00S H 0.3837 0.3134 0.4686 0.078 Uiso 1 1 calc R . . . .
C00T C 0.8644(15) 0.5013(14) 0.2012(10) 0.066(4) Uani 1 1 d . . . . .
H00T H 0.8115 0.5274 0.2456 0.079 Uiso 1 1 calc R . . . .
C00V C 0.2498(16) 0.5314(12) 0.4615(9) 0.058(4) Uani 1 1 d . . . . .
H00V H 0.1908 0.5824 0.4873 0.070 Uiso 1 1 calc R . . . .
C00W C 0.3630(17) 0.8074(12) 0.4774(10) 0.059(4) Uani 1 1 d . . . . .
C00X C 0.2787(17) 0.4491(14) 0.4921(10) 0.065(4) Uani 1 1 d . . . . .
C00Y C 0.6437(17) 0.2589(13) 0.1628(12) 0.069(5) Uani 1 1 d . . . . .
H00Y H 0.7230 0.2992 0.1692 0.083 Uiso 1 1 calc R . . . .
C00Z C 0.7867(16) 0.8331(13) 0.0525(10) 0.066(4) Uani 1 1 d . . . . .
H00Z H 0.7134 0.8429 0.0178 0.079 Uiso 1 1 calc R . . . .
C010 C 0.8728(17) 0.7802(16) 0.1712(11) 0.076(5) Uani 1 1 d . . . . .
H010 H 0.8581 0.7550 0.2152 0.091 Uiso 1 1 calc R . . . .
C011 C 0.337(2) 0.8271(14) 0.5611(12) 0.084(6) Uani 1 1 d . . . . .
H011 H 0.2572 0.8017 0.5716 0.101 Uiso 1 1 calc R . . . .
C012 C 0.4785(18) 0.8438(14) 0.4586(11) 0.071(5) Uani 1 1 d . . . . .
H012 H 0.4917 0.8307 0.4013 0.085 Uiso 1 1 calc R . . . .
C013 C 0.405(2) 0.1385(13) 0.1374(10) 0.072(5) Uani 1 1 d . . . . .
H013 H 0.3248 0.0982 0.1276 0.087 Uiso 1 1 calc R . . . .
C015 C 1.0825(18) 0.4637(15) 0.1604(14) 0.079(5) Uani 1 1 d . . . . .
H015 H 1.1737 0.4617 0.1738 0.094 Uiso 1 1 calc R . . . .
C016 C 0.553(2) 0.9216(14) 0.6121(13) 0.086(6) Uani 1 1 d . . . . .
C017 C 1.024(2) 0.8392(14) 0.0927(13) 0.082(6) Uani 1 1 d . . . . .
C018 C 0.643(2) 0.1505(15) 0.1372(13) 0.088(6) Uani 1 1 d . . . . .
H018 H 0.7231 0.1169 0.1289 0.105 Uiso 1 1 calc R . . . .
C019 C 1.0229(17) 0.4240(14) 0.0719(13) 0.075(5) Uani 1 1 d . . . . .
H019 H 1.0759 0.3987 0.0274 0.090 Uiso 1 1 calc R . . . .
C01A C 1.0068(19) 0.8026(17) 0.1579(13) 0.088(6) Uani 1 1 d . . . . .
H01A H 1.0794 0.7923 0.1929 0.106 Uiso 1 1 calc R . . . .
C01B C 1.0059(17) 0.5039(16) 0.2240(13) 0.077(5) Uani 1 1 d . . . . .
H01B H 1.0436 0.5330 0.2818 0.093 Uiso 1 1 calc R . . . .
C01C C 0.522(2) 0.0863(14) 0.1226(11) 0.077(5) Uani 1 1 d . . . . .
H01C H 0.5211 0.0112 0.1035 0.092 Uiso 1 1 calc R . . . .
C01D C 0.434(2) 0.8862(16) 0.6307(13) 0.088(6) Uani 1 1 d . . . . .
H01D H 0.4189 0.9012 0.6880 0.105 Uiso 1 1 calc R . . . .
C01E C 0.227(2) 0.4436(17) 0.5720(10) 0.089(6) Uani 1 1 d . . . . .
H01E H 0.1886 0.3719 0.5597 0.134 Uiso 1 1 calc GR . . . .
H01F H 0.1601 0.4949 0.5887 0.134 Uiso 1 1 calc GR . . . .
H01G H 0.2987 0.4606 0.6185 0.134 Uiso 1 1 calc GR . . . .
C01F C 0.576(2) 0.9005(15) 0.5266(14) 0.084(6) Uani 1 1 d . . . . .
H01H H 0.6561 0.9245 0.5149 0.100 Uiso 1 1 calc R . . . .
C01G C 0.663(2) 0.9807(17) 0.6842(14) 0.104(7) Uani 1 1 d . . . . .
H01I H 0.6395 1.0533 0.7140 0.156 Uiso 1 1 calc GR . . . .
H01J H 0.7443 0.9828 0.6601 0.156 Uiso 1 1 calc GR . . . .
H01K H 0.6745 0.9436 0.7245 0.156 Uiso 1 1 calc GR . . . .
O0AA O 0.5141(10) 0.7849(9) 0.0712(8) 0.075(3) Uani 1 1 d . . . . .
C1AA C 0.912(2) 0.8547(16) 0.0379(12) 0.082(5) Uani 1 1 d . . . . .
H1AA H 0.9249 0.8792 -0.0069 0.098 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
Br01 C017 1.867(19) . ?
S03 O006 1.416(10) . ?
S03 N009 1.660(12) . ?
S03 O00A 1.430(11) . ?
S03 C00W 1.761(17) . ?
O004 C00C 1.197(15) . ?
N005 S008 1.663(11) . ?
N005 C00C 1.375(17) . ?
N005 C00E 1.494(15) . ?
O007 S008 1.389(11) . ?
S008 C00Q 1.761(14) . ?
S008 O0AA 1.417(11) . ?
N009 C00F 1.425(16) . ?
N009 C00M 1.402(17) . ?
C00C C00I 1.550(18) . ?
C00D C00F 1.361(18) . ?
C00D C00H 1.475(17) . ?
C00D C00J 1.473(17) . ?
C00E H00E 0.9800 . ?
C00E C00G 1.554(17) . ?
C00E C00P 1.509(18) . ?
C00F C00P 1.497(17) . ?
C00G C00I 1.506(17) . ?
C00G C00J 1.311(17) . ?
C00H C00M 1.381(19) . ?
C00H C00N 1.404(19) . ?
C00I H00I 0.9800 . ?
C00I C00K 1.529(18) . ?
C00J C00L 1.481(18) . ?
C00K C00R 1.38(2) . ?
C00K C00T 1.321(19) . ?
C00L C00O 1.375(19) . ?
C00L C00Y 1.44(2) . ?
C00M C00V 1.403(19) . ?
C00N H00N 0.9300 . ?
C00N C00S 1.38(2) . ?
C00O H00O 0.9300 . ?
C00O C013 1.37(2) . ?
C00P H00A 0.9700 . ?
C00P H00B 0.9700 . ?
C00Q C00Z 1.40(2) . ?
C00Q C010 1.35(2) . ?
C00R H00R 0.9300 . ?
C00R C019 1.45(2) . ?
C00S H00S 0.9300 . ?
C00S C00X 1.43(2) . ?
C00T H00T 0.9300 . ?
C00T C01B 1.44(2) . ?
C00V H00V 0.9300 . ?
C00V C00X 1.38(2) . ?
C00W C011 1.37(2) . ?
C00W C012 1.36(2) . ?
C00X C01E 1.50(2) . ?
C00Y H00Y 0.9300 . ?
C00Y C018 1.34(2) . ?
C00Z H00Z 0.9300 . ?
C00Z C1AA 1.36(2) . ?
C010 H010 0.9300 . ?
C010 C01A 1.44(2) . ?
C011 H011 0.9300 . ?
C011 C01D 1.41(3) . ?
C012 H012 0.9300 . ?
C012 C01F 1.39(2) . ?
C013 H013 0.9300 . ?
C013 C01C 1.38(3) . ?
C015 H015 0.9300 . ?
C015 C019 1.43(3) . ?
C015 C01B 1.34(3) . ?
C016 C01D 1.39(3) . ?
C016 C01F 1.39(3) . ?
C016 C01G 1.51(3) . ?
C017 C01A 1.36(3) . ?
C017 C1AA 1.44(3) . ?
C018 H018 0.9300 . ?
C018 C01C 1.43(3) . ?
C019 H019 0.9300 . ?
C01A H01A 0.9300 . ?
C01B H01B 0.9300 . ?
C01C H01C 0.9300 . ?
C01D H01D 0.9300 . ?
C01E H01E 0.9600 . ?
C01E H01F 0.9600 . ?
C01E H01G 0.9600 . ?
C01F H01H 0.9300 . ?
C01G H01I 0.9601 . ?
C01G H01J 0.9601 . ?
C01G H01K 0.9601 . ?
C1AA H1AA 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
O006 S03 N009 106.8(6) . . ?
O006 S03 O00A 118.9(7) . . ?
O006 S03 C00W 110.9(7) . . ?
N009 S03 C00W 104.0(6) . . ?
O00A S03 N009 105.6(6) . . ?
O00A S03 C00W 109.4(7) . . ?
C00C N005 S008 124.0(9) . . ?
C00C N005 C00E 114.9(10) . . ?
C00E N005 S008 120.8(9) . . ?
N005 S008 C00Q 104.2(6) . . ?
O007 S008 N005 105.1(6) . . ?
O007 S008 C00Q 109.2(7) . . ?
O007 S008 O0AA 118.4(8) . . ?
O0AA S008 N005 109.7(6) . . ?
O0AA S008 C00Q 109.2(7) . . ?
C00F N009 S03 125.5(9) . . ?
C00M N009 S03 124.3(9) . . ?
C00M N009 C00F 107.3(10) . . ?
O004 C00C N005 124.8(13) . . ?
O004 C00C C00I 127.4(12) . . ?
N005 C00C C00I 107.5(11) . . ?
C00F C00D C00H 106.6(11) . . ?
C00F C00D C00J 120.6(11) . . ?
C00H C00D C00J 132.7(12) . . ?
N005 C00E H00E 110.3 . . ?
N005 C00E C00G 101.3(9) . . ?
N005 C00E C00P 113.0(10) . . ?
C00G C00E H00E 110.3 . . ?
C00P C00E H00E 110.3 . . ?
C00P C00E C00G 111.3(10) . . ?
N009 C00F C00P 129.1(12) . . ?
C00D C00F N009 109.7(11) . . ?
C00D C00F C00P 121.2(12) . . ?
C00I C00G C00E 109.0(10) . . ?
C00J C00G C00E 119.3(11) . . ?
C00J C00G C00I 131.3(11) . . ?
C00M C00H C00D 107.4(12) . . ?
C00N C00H C00D 131.3(13) . . ?
C00N C00H C00M 121.2(13) . . ?
C00C C00I H00I 110.7 . . ?
C00C C00I C00K 106.3(10) . . ?
C00G C00I C00C 103.1(10) . . ?
C00G C00I H00I 110.7 . . ?
C00G C00I C00K 114.8(10) . . ?
C00K C00I H00I 110.7 . . ?
C00D C00J C00L 118.2(11) . . ?
C00G C00J C00D 116.5(11) . . ?
C00G C00J C00L 125.2(11) . . ?
C00R C00K C00I 117.4(12) . . ?
C00T C00K C00I 121.5(12) . . ?
C00T C00K C00R 121.0(14) . . ?
C00O C00L C00J 121.0(12) . . ?
C00O C00L C00Y 117.0(13) . . ?
C00Y C00L C00J 122.0(12) . . ?
C00H C00M N009 108.9(11) . . ?
C00V C00M N009 130.0(13) . . ?
C00V C00M C00H 121.1(13) . . ?
C00H C00N H00N 121.3 . . ?
C00S C00N C00H 117.3(15) . . ?
C00S C00N H00N 121.3 . . ?
C00L C00O H00O 118.7 . . ?
C013 C00O C00L 122.6(16) . . ?
C013 C00O H00O 118.7 . . ?
C00E C00P H00A 110.6 . . ?
C00E C00P H00B 110.7 . . ?
C00F C00P C00E 105.5(10) . . ?
C00F C00P H00A 110.6 . . ?
C00F C00P H00B 110.6 . . ?
H00A C00P H00B 108.8 . . ?
C00Z C00Q S008 118.1(11) . . ?
C00Z C00Q C010 121.4(14) . . ?
C010 C00Q S008 120.5(11) . . ?
C00K C00R H00R 121.2 . . ?
C00K C00R C019 117.6(15) . . ?
C019 C00R H00R 121.2 . . ?
C00N C00S H00S 118.9 . . ?
C00N C00S C00X 122.2(15) . . ?
C00X C00S H00S 118.9 . . ?
C00K C00T H00T 118.6 . . ?
C00K C00T C01B 122.9(15) . . ?
C01B C00T H00T 118.5 . . ?
C00M C00V H00V 120.5 . . ?
C00X C00V C00M 119.1(14) . . ?
C00X C00V H00V 120.4 . . ?
C011 C00W S03 118.0(15) . . ?
C012 C00W S03 119.3(13) . . ?
C012 C00W C011 122.7(17) . . ?
C00S C00X C01E 118.9(15) . . ?
C00V C00X C00S 118.9(13) . . ?
C00V C00X C01E 122.1(16) . . ?
C00L C00Y H00Y 119.6 . . ?
C018 C00Y C00L 121.0(16) . . ?
C018 C00Y H00Y 119.5 . . ?
C00Q C00Z H00Z 120.0 . . ?
C00Q C00Z C1AA 120.0(16) . . ?
C1AA C00Z H00Z 120.0 . . ?
C00Q C010 H010 119.9 . . ?
C01A C010 C00Q 120.3(15) . . ?
C01A C010 H010 119.8 . . ?
C00W C011 H011 120.5 . . ?
C01D C011 C00W 119(2) . . ?
C01D C011 H011 120.4 . . ?
C00W C012 H012 120.6 . . ?
C00W C012 C01F 118.9(17) . . ?
C01F C012 H012 120.5 . . ?
C00O C013 H013 119.9 . . ?
C00O C013 C01C 120.3(17) . . ?
C01C C013 H013 119.8 . . ?
C019 C015 H015 120.3 . . ?
C019 C015 C01B 119.4(16) . . ?
C01B C015 H015 120.3 . . ?
C01D C016 C01F 120.8(19) . . ?
C01D C016 C01G 121(2) . . ?
C01F C016 C01G 119(2) . . ?
C01A C017 Br01 119.5(17) . . ?
C01A C017 C1AA 121.3(17) . . ?
C1AA C017 Br01 119.2(14) . . ?
C00Y C018 H018 119.7 . . ?
C01C C018 C00Y 120.5(17) . . ?
C01C C018 H018 119.7 . . ?
C00R C019 H019 119.9 . . ?
C015 C019 C00R 120.1(16) . . ?
C015 C019 H019 120.0 . . ?
C010 C01A H01A 121.0 . . ?
C017 C01A C010 118.0(17) . . ?
C017 C01A H01A 121.0 . . ?
C00T C01B C015 118.9(16) . . ?
C00T C01B H01B 120.6 . . ?
C015 C01B H01B 120.5 . . ?
C013 C01C H01C 120.8 . . ?
C018 C01C C013 118.5(16) . . ?
C018 C01C H01C 120.7 . . ?
C011 C01D C016 118.6(19) . . ?
C011 C01D H01D 120.7 . . ?
C016 C01D H01D 120.7 . . ?
C00X C01E H01E 109.5 . . ?
C00X C01E H01F 109.4 . . ?
C00X C01E H01G 109.6 . . ?
H01E C01E H01F 109.5 . . ?
H01E C01E H01G 109.5 . . ?
H01F C01E H01G 109.5 . . ?
C012 C01F C016 120(2) . . ?
C012 C01F H01H 120.1 . . ?
C016 C01F H01H 120.0 . . ?
C016 C01G H01I 109.5 . . ?
C016 C01G H01J 109.5 . . ?
C016 C01G H01K 109.4 . . ?
H01I C01G H01J 109.5 . . ?
H01I C01G H01K 109.5 . . ?
H01J C01G H01K 109.5 . . ?
C00Z C1AA H1AA 120.5 . . ?
C017 C1AA C00Z 119.0(16) . . ?
C017 C1AA H1AA 120.4 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: hexane and ethyl acetate'
####################################################################### 
# 
# 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_exp_1657
_database_code_depnum_ccdc_archive 'CCDC 1569443'
_audit_update_record             
;
2017-08-17 deposited with the CCDC.
2018-06-18 downloaded from the CCDC.
;
_audit_creation_date             2016-08-05
_audit_creation_method           
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_chemical_name_common            ?
_chemical_name_systematic        
(3R,3aS,4R,9aS)-1-(methylsulfonyl)-3,4-diphenyl-3a,4,9,9a-tetrahydro-1H-benzo[f]indol-2(3H)-one
_chemical_formula_moiety         'C25 H23 N O3 S'
_chemical_formula_sum            'C25 H23 N O3 S'
_chemical_formula_weight         417.50
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   18.5095(15)
_cell_length_b                   10.9007(8)
_cell_length_c                   10.3745(8)
_cell_angle_alpha                90
_cell_angle_beta                 103.857(8)
_cell_angle_gamma                90
_cell_volume                     2032.3(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1488
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      65.3310
_cell_measurement_theta_min      4.7290
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    1.637
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.87798
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.365
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             880
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0774
_diffrn_reflns_av_unetI/netI     0.0912
_diffrn_reflns_Laue_measured_fraction_full 0.965
_diffrn_reflns_Laue_measured_fraction_max 0.965
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_number            7032
_diffrn_reflns_point_group_measured_fraction_full 0.965
_diffrn_reflns_point_group_measured_fraction_max 0.965
_diffrn_reflns_theta_full        65.949
_diffrn_reflns_theta_max         65.949
_diffrn_reflns_theta_min         4.745
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.4741
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.965
_diffrn_measured_fraction_theta_max 0.965
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -49.00   33.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.5047   37.0000   60.0000 82

#__ type_ start__ end____ width___ exp.time_
  2 omega  -87.00  -16.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.5047  125.0000   90.0000 71

#__ type_ start__ end____ width___ exp.time_
  3 omega  -94.00  -28.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.5047  125.0000  -30.0000 66

#__ type_ start__ end____ width___ exp.time_
  4 omega   21.00  113.00   1.0000   12.5000
omega____ theta____ kappa____ phi______ frames
    -       91.1609  -61.0000 -180.0000 92

#__ type_ start__ end____ width___ exp.time_
  5 omega   61.00   98.00   1.0000   12.5000
omega____ theta____ kappa____ phi______ frames
    -       91.1609   61.0000  -30.0000 37

#__ type_ start__ end____ width___ exp.time_
  6 omega  131.00  158.00   1.0000   12.5000
omega____ theta____ kappa____ phi______ frames
    -       91.1609   61.0000  -30.0000 27

#__ type_ start__ end____ width___ exp.time_
  7 omega  129.00  178.00   1.0000   12.5000
omega____ theta____ kappa____ phi______ frames
    -       91.1609    0.0000   30.0000 49

#__ type_ start__ end____ width___ exp.time_
  8 omega  109.00  150.00   1.0000   12.5000
omega____ theta____ kappa____ phi______ frames
    -       91.1609  125.0000 -180.0000 41

#__ type_ start__ end____ width___ exp.time_
  9 omega   32.00  105.00   1.0000   12.5000
omega____ theta____ kappa____ phi______ frames
    -       91.1609    0.0000   30.0000 73

#__ type_ start__ end____ width___ exp.time_
 10 omega   13.00   73.00   1.0000   12.5000
omega____ theta____ kappa____ phi______ frames
    -       91.1609  -30.0000 -150.0000 60
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0670602000
_diffrn_orient_matrix_UB_12      -0.0433579000
_diffrn_orient_matrix_UB_13      -0.1090099000
_diffrn_orient_matrix_UB_21      0.0410064000
_diffrn_orient_matrix_UB_22      -0.1207236000
_diffrn_orient_matrix_UB_23      -0.0128781000
_diffrn_orient_matrix_UB_31      -0.0342151000
_diffrn_orient_matrix_UB_32      -0.0594936000
_diffrn_orient_matrix_UB_33      0.1064101000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2384
_reflns_number_total             3416
_reflns_odcompleteness_completeness 99.88
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     61.08
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_refine_diff_density_max         0.351
_refine_diff_density_min         -0.429
_refine_diff_density_rms         0.074
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     272
_refine_ls_number_reflns         3416
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0881
_refine_ls_R_factor_gt           0.0583
_refine_ls_restrained_S_all      1.028
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0660P)²+0.3900P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1418
_refine_ls_wR_factor_ref         0.1675
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C3(H3), C4(H4), C2(H2), C12(H12)
2.b Secondary CH2 refined with riding coordinates:
 C11(H11A,H11B)
2.c Aromatic/amide H refined with riding coordinates:
 C25(H25), C6(H6), C8(H8), C9(H9), C19(H19), C22(H22), C21(H21), C15(H15),
 C23(H23), C7(H7), C24(H24), C18(H18), C16(H16), C17(H17)
2.d Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.16385(5) 0.05210(8) 0.39914(9) 0.0226(3) Uani 1 1 d . . . . .
O2 O 0.21847(14) -0.0137(2) 0.4953(3) 0.0305(6) Uani 1 1 d . . . . .
O3 O 0.15143(16) 0.0213(3) 0.2626(3) 0.0341(7) Uani 1 1 d . . . . .
O1 O 0.11354(14) 0.2820(2) 0.2289(2) 0.0291(6) Uani 1 1 d . . . . .
C13 C 0.0798(2) 0.0508(4) 0.4465(4) 0.0270(9) Uani 1 1 d . . . . .
H13A H 0.0622 -0.0321 0.4463 0.041 Uiso 1 1 calc GR . . . .
H13B H 0.0439 0.0991 0.3853 0.041 Uiso 1 1 calc GR . . . .
H13C H 0.0870 0.0845 0.5342 0.041 Uiso 1 1 calc GR . . . .
N1 N 0.19086(15) 0.1979(3) 0.4176(3) 0.0204(7) Uani 1 1 d . . . . .
C3 C 0.23308(18) 0.3812(3) 0.5345(3) 0.0171(7) Uani 1 1 d . . . . .
H3 H 0.1927 0.3943 0.5793 0.020 Uiso 1 1 calc R . . . .
C25 C 0.38064(19) 0.5173(3) 0.4502(3) 0.0216(8) Uani 1 1 d . . . . .
H25 H 0.3997 0.4380 0.4573 0.026 Uiso 1 1 calc R . . . .
C11 C 0.32614(19) 0.2115(3) 0.5259(3) 0.0205(8) Uani 1 1 d . . . . .
H11A H 0.3326 0.1234 0.5227 0.025 Uiso 1 1 calc R . . . .
H11B H 0.3357 0.2470 0.4458 0.025 Uiso 1 1 calc R . . . .
C4 C 0.30150(18) 0.4596(3) 0.6117(3) 0.0187(7) Uani 1 1 d . . . . .
H4 H 0.2836 0.5085 0.6771 0.022 Uiso 1 1 calc R . . . .
C10 C 0.37928(18) 0.2640(3) 0.6464(3) 0.0182(7) Uani 1 1 d . . . . .
C6 C 0.41315(19) 0.4281(3) 0.8035(3) 0.0206(8) Uani 1 1 d . . . . .
H6 H 0.4044 0.5060 0.8331 0.025 Uiso 1 1 calc R . . . .
C20 C 0.32985(18) 0.5509(3) 0.5233(3) 0.0174(7) Uani 1 1 d . . . . .
C8 C 0.4866(2) 0.2444(3) 0.8315(4) 0.0229(8) Uani 1 1 d . . . . .
H8 H 0.5265 0.1985 0.8790 0.028 Uiso 1 1 calc R . . . .
C9 C 0.43972(19) 0.1967(3) 0.7178(3) 0.0216(8) Uani 1 1 d . . . . .
H9 H 0.4487 0.1187 0.6889 0.026 Uiso 1 1 calc R . . . .
C19 C 0.1656(2) 0.6090(3) 0.2618(4) 0.0262(8) Uani 1 1 d . . . . .
H19 H 0.2047 0.5966 0.2212 0.031 Uiso 1 1 calc R . . . .
C5 C 0.36554(18) 0.3818(3) 0.6900(3) 0.0172(7) Uani 1 1 d . . . . .
C14 C 0.15294(18) 0.5242(3) 0.3534(3) 0.0210(8) Uani 1 1 d . . . . .
C22 C 0.3265(2) 0.7555(3) 0.4311(4) 0.0252(8) Uani 1 1 d . . . . .
H22 H 0.3084 0.8355 0.4253 0.030 Uiso 1 1 calc R . . . .
C2 C 0.20177(19) 0.4119(3) 0.3869(3) 0.0184(7) Uani 1 1 d . . . . .
H2 H 0.2441 0.4224 0.3464 0.022 Uiso 1 1 calc R . . . .
C12 C 0.24762(18) 0.2414(3) 0.5353(3) 0.0187(7) Uani 1 1 d . . . . .
H12 H 0.2382 0.2050 0.6160 0.022 Uiso 1 1 calc R . . . .
C21 C 0.30448(19) 0.6725(3) 0.5138(4) 0.0220(8) Uani 1 1 d . . . . .
H21 H 0.2720 0.6975 0.5647 0.026 Uiso 1 1 calc R . . . .
C15 C 0.0933(2) 0.5441(4) 0.4120(4) 0.0292(9) Uani 1 1 d . . . . .
H15 H 0.0835 0.4883 0.4734 0.035 Uiso 1 1 calc R . . . .
C23 C 0.3758(2) 0.7198(3) 0.3561(4) 0.0248(8) Uani 1 1 d . . . . .
H23 H 0.3904 0.7751 0.2990 0.030 Uiso 1 1 calc R . . . .
C7 C 0.47333(19) 0.3613(3) 0.8737(4) 0.0221(8) Uani 1 1 d . . . . .
H7 H 0.5048 0.3946 0.9491 0.027 Uiso 1 1 calc R . . . .
C24 C 0.4031(2) 0.6005(3) 0.3671(4) 0.0251(8) Uani 1 1 d . . . . .
H24 H 0.4367 0.5765 0.3181 0.030 Uiso 1 1 calc R . . . .
C18 C 0.1210(2) 0.7118(4) 0.2295(4) 0.0336(10) Uani 1 1 d . . . . .
H18 H 0.1306 0.7685 0.1688 0.040 Uiso 1 1 calc R . . . .
C1 C 0.16173(19) 0.2938(3) 0.3312(3) 0.0205(8) Uani 1 1 d . . . . .
C16 C 0.0490(2) 0.6465(4) 0.3786(4) 0.0346(10) Uani 1 1 d . . . . .
H16 H 0.0095 0.6593 0.4181 0.042 Uiso 1 1 calc R . . . .
C17 C 0.0623(2) 0.7298(4) 0.2877(4) 0.0337(10) Uani 1 1 d . . . . .
H17 H 0.0318 0.7982 0.2655 0.040 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 1.431(3) . ?
S1 O3 1.420(3) . ?
S1 C13 1.740(3) . ?
S1 N1 1.663(3) . ?
O1 C1 1.219(4) . ?
N1 C12 1.485(4) . ?
N1 C1 1.399(4) . ?
C3 C4 1.578(5) . ?
C3 C2 1.539(5) . ?
C3 C12 1.547(5) . ?
C25 C20 1.391(5) . ?
C25 C24 1.382(5) . ?
C11 C10 1.507(5) . ?
C11 C12 1.515(5) . ?
C4 C20 1.529(5) . ?
C4 C5 1.524(5) . ?
C10 C9 1.394(5) . ?
C10 C5 1.404(5) . ?
C6 C5 1.386(5) . ?
C6 C7 1.383(5) . ?
C20 C21 1.401(5) . ?
C8 C9 1.387(5) . ?
C8 C7 1.389(5) . ?
C19 C14 1.386(5) . ?
C19 C18 1.385(6) . ?
C14 C2 1.512(5) . ?
C14 C15 1.399(5) . ?
C22 C21 1.375(5) . ?
C22 C23 1.390(5) . ?
C2 C1 1.527(5) . ?
C15 C16 1.380(6) . ?
C23 C24 1.390(5) . ?
C18 C17 1.378(6) . ?
C16 C17 1.373(6) . ?

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 C13 109.22(17) . . ?
O2 S1 N1 104.84(15) . . ?
O3 S1 O2 119.67(17) . . ?
O3 S1 C13 109.74(18) . . ?
O3 S1 N1 108.25(16) . . ?
N1 S1 C13 103.88(17) . . ?
C12 N1 S1 122.3(2) . . ?
C1 N1 S1 125.6(2) . . ?
C1 N1 C12 112.1(3) . . ?
C2 C3 C4 116.9(3) . . ?
C2 C3 C12 104.0(3) . . ?
C12 C3 C4 114.4(3) . . ?
C24 C25 C20 120.7(3) . . ?
C10 C11 C12 108.1(3) . . ?
C20 C4 C3 113.4(3) . . ?
C5 C4 C3 113.4(3) . . ?
C5 C4 C20 110.3(3) . . ?
C9 C10 C11 121.5(3) . . ?
C9 C10 C5 119.6(3) . . ?
C5 C10 C11 118.8(3) . . ?
C7 C6 C5 121.6(3) . . ?
C25 C20 C4 122.0(3) . . ?
C25 C20 C21 118.0(3) . . ?
C21 C20 C4 120.0(3) . . ?
C9 C8 C7 119.4(3) . . ?
C8 C9 C10 120.9(3) . . ?
C18 C19 C14 121.1(4) . . ?
C10 C5 C4 121.0(3) . . ?
C6 C5 C4 120.3(3) . . ?
C6 C5 C10 118.6(3) . . ?
C19 C14 C2 120.5(3) . . ?
C19 C14 C15 118.4(3) . . ?
C15 C14 C2 121.1(3) . . ?
C21 C22 C23 119.8(3) . . ?
C14 C2 C3 117.8(3) . . ?
C14 C2 C1 112.7(3) . . ?
C1 C2 C3 103.1(3) . . ?
N1 C12 C3 102.9(3) . . ?
N1 C12 C11 112.3(3) . . ?
C11 C12 C3 112.3(3) . . ?
C22 C21 C20 121.5(3) . . ?
C16 C15 C14 120.0(4) . . ?
C24 C23 C22 119.4(3) . . ?
C6 C7 C8 119.9(3) . . ?
C25 C24 C23 120.5(3) . . ?
C17 C18 C19 119.8(4) . . ?
O1 C1 N1 124.6(3) . . ?
O1 C1 C2 127.3(3) . . ?
N1 C1 C2 108.1(3) . . ?
C17 C16 C15 120.9(4) . . ?
C16 C17 C18 119.8(4) . . ?

_shelx_SHELXL_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: hexane and ethyl acetate'
####################################################################### 
# 
# 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_exp_6994
_database_code_depnum_ccdc_archive 'CCDC 1569444'
_audit_update_record             
;
2017-08-17 deposited with the CCDC.
2018-06-18 downloaded from the CCDC.
;
_audit_creation_date             2017-08-17
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5375)
;
_shelxl_version_number           2014-3
_chemical_name_common            ?
_chemical_name_systematic        
(3R,9aS)-3,4-diphenyl-1-tosyl-9,9a-dihydro-1H-benzo[f]indol-2(3H)-one
_chemical_formula_moiety         'C31 H25 N O3 S'
_chemical_formula_sum            'C31 H25 N O3 S'
_chemical_formula_weight         491.58
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   11.7246(4)
_cell_length_b                   12.2563(6)
_cell_length_c                   16.5665(7)
_cell_angle_alpha                90
_cell_angle_beta                 98.550(4)
_cell_angle_gamma                90
_cell_volume                     2354.15(18)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4594
_cell_measurement_temperature    99.97(10)
_cell_measurement_theta_max      65.5040
_cell_measurement_theta_min      3.8170
_shelx_estimated_absorpt_T_max   0.828
_shelx_estimated_absorpt_T_min   0.629
_exptl_absorpt_coefficient_mu    1.505
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.75386
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.387
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1032
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.13
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0336
_diffrn_reflns_av_unetI/netI     0.0369
_diffrn_reflns_Laue_measured_fraction_full 0.926
_diffrn_reflns_Laue_measured_fraction_max 0.983
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            8354
_diffrn_reflns_point_group_measured_fraction_full 0.926
_diffrn_reflns_point_group_measured_fraction_max 0.983
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         64.995
_diffrn_reflns_theta_min         4.332
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      99.97(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.4741
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.926
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega   81.00  165.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       91.1609   45.0000  -60.0000 84

#__ type_ start__ end____ width___ exp.time_
  2 omega  130.00  164.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       91.1609  125.0000   60.0000 34

#__ type_ start__ end____ width___ exp.time_
  3 omega   94.00  152.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       91.1609  125.0000  120.0000 58

#__ type_ start__ end____ width___ exp.time_
  4 omega   81.00  165.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       91.1609   61.0000 -120.0000 84

#__ type_ start__ end____ width___ exp.time_
  5 omega   33.00   58.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       40.7547 -125.0000  -30.0000 25

#__ type_ start__ end____ width___ exp.time_
  6 omega   47.00  121.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       91.1609 -125.0000 -120.0000 74

#__ type_ start__ end____ width___ exp.time_
  7 omega   15.00   85.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       91.1609  -30.0000   90.0000 70

#__ type_ start__ end____ width___ exp.time_
  8 omega  -48.00   35.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.7547   37.0000   60.0000 83

#__ type_ start__ end____ width___ exp.time_
  9 omega  -90.00   -2.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.7547  125.0000   90.0000 88
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.1128876000
_diffrn_orient_matrix_UB_12      0.0085890000
_diffrn_orient_matrix_UB_13      0.0605725000
_diffrn_orient_matrix_UB_21      0.0208535000
_diffrn_orient_matrix_UB_22      0.1151762000
_diffrn_orient_matrix_UB_23      -0.0322299000
_diffrn_orient_matrix_UB_31      -0.0667843000
_diffrn_orient_matrix_UB_32      0.0502018000
_diffrn_orient_matrix_UB_33      0.0641542000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3487
_reflns_number_total             3942
_reflns_odcompleteness_completeness 99.95
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     61.08
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_refine_diff_density_max         0.347
_refine_diff_density_min         -0.441
_refine_diff_density_rms         0.056
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     326
_refine_ls_number_reflns         3942
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0498
_refine_ls_R_factor_gt           0.0430
_refine_ls_restrained_S_all      1.035
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0573P)²+1.7449P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1092
_refine_ls_wR_factor_ref         0.1149
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C15(H15), C27(H27)
2.b Secondary CH2 refined with riding coordinates:
 C35(H35A,H35B)
2.c Aromatic/amide H refined with riding coordinates:
 C6(H6), C14(H14), C16(H16), C17(H17), C18(H18), C20(H20), C21(H21), C22(H22),
 C23(H23), C24(H24), C25(H25), C26(H26), C28(H28), C29(H29), C30(H30), C31(H31),
  C32(H32), C34(H34)
2.d Idealised Me refined as rotating group:
 C33(H33A,H33B,H33C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.15673(4) 0.77916(4) 0.46266(3) 0.02013(16) Uani 1 1 d . . . . .
O1 O 0.04972(12) 0.79958(12) 0.49033(8) 0.0248(3) Uani 1 1 d . . . . .
O2 O 0.23303(12) 0.86718(12) 0.45266(9) 0.0257(3) Uani 1 1 d . . . . .
O3 O 0.07640(12) 0.60079(13) 0.57119(9) 0.0278(4) Uani 1 1 d . . . . .
N4 N 0.23197(13) 0.69434(14) 0.53094(10) 0.0189(4) Uani 1 1 d . . . . .
C5 C 0.13474(16) 0.70197(17) 0.37223(12) 0.0203(4) Uani 1 1 d . . . . .
C6 C 0.19984(17) 0.72449(17) 0.31063(12) 0.0224(4) Uani 1 1 d . . . . .
H6 H 0.2555 0.7814 0.3169 0.027 Uiso 1 1 calc R . . . .
C7 C 0.51250(16) 0.46993(17) 0.68694(12) 0.0198(4) Uani 1 1 d . . . . .
C8 C 0.27197(16) 0.54734(17) 0.71084(12) 0.0207(4) Uani 1 1 d . . . . .
C9 C 0.58474(17) 0.61349(17) 0.59205(12) 0.0204(4) Uani 1 1 d . . . . .
C10 C 0.38111(17) 0.58282(17) 0.59240(12) 0.0201(4) Uani 1 1 d . . . . .
C11 C 0.17836(16) 0.61294(17) 0.57246(12) 0.0207(4) Uani 1 1 d . . . . .
C12 C 0.10296(17) 0.57736(18) 0.23098(12) 0.0249(5) Uani 1 1 d . . . . .
C13 C 0.49075(17) 0.55540(17) 0.62220(12) 0.0200(4) Uani 1 1 d . . . . .
C14 C 0.47926(17) 0.36276(17) 0.67107(13) 0.0240(5) Uani 1 1 d . . . . .
H14 H 0.4528 0.3405 0.6166 0.029 Uiso 1 1 calc R . . . .
C15 C 0.27229(16) 0.54130(17) 0.61921(12) 0.0208(4) Uani 1 1 d . . . . .
H15 H 0.2595 0.4639 0.6009 0.025 Uiso 1 1 calc R . . . .
C16 C 0.69839(17) 0.57450(19) 0.60455(13) 0.0254(5) Uani 1 1 d . . . . .
H16 H 0.7160 0.5091 0.6346 0.031 Uiso 1 1 calc R . . . .
C17 C 0.05393(17) 0.61842(18) 0.36471(12) 0.0227(4) Uani 1 1 d . . . . .
H17 H 0.0094 0.6043 0.4070 0.027 Uiso 1 1 calc R . . . .
C18 C 0.55553(17) 0.49958(18) 0.76736(12) 0.0242(5) Uani 1 1 d . . . . .
H18 H 0.5828 0.5717 0.7789 0.029 Uiso 1 1 calc R . . . .
C19 C 0.56010(17) 0.71117(18) 0.54804(12) 0.0239(5) Uani 1 1 d . . . . .
C20 C 0.18222(18) 0.66260(18) 0.23986(13) 0.0259(5) Uani 1 1 d . . . . .
H20 H 0.2249 0.6786 0.1968 0.031 Uiso 1 1 calc R . . . .
C21 C 0.64928(17) 0.76641(19) 0.51841(13) 0.0253(5) Uani 1 1 d . . . . .
H21 H 0.6333 0.8328 0.4894 0.030 Uiso 1 1 calc R . . . .
C22 C 0.03973(17) 0.55614(18) 0.29421(13) 0.0242(5) Uani 1 1 d . . . . .
H22 H -0.0142 0.4978 0.2888 0.029 Uiso 1 1 calc R . . . .
C23 C 0.76068(17) 0.72594(18) 0.53065(12) 0.0237(5) Uani 1 1 d . . . . .
H23 H 0.8204 0.7640 0.5095 0.028 Uiso 1 1 calc R . . . .
C24 C 0.25726(19) 0.45923(19) 0.83872(13) 0.0295(5) Uani 1 1 d . . . . .
H24 H 0.2419 0.3957 0.8681 0.035 Uiso 1 1 calc R . . . .
C25 C 0.24987(17) 0.45541(18) 0.75430(13) 0.0244(5) Uani 1 1 d . . . . .
H25 H 0.2295 0.3890 0.7262 0.029 Uiso 1 1 calc R . . . .
C26 C 0.78498(17) 0.62960(19) 0.57389(13) 0.0262(5) Uani 1 1 d . . . . .
H26 H 0.8614 0.6016 0.5823 0.031 Uiso 1 1 calc R . . . .
C27 C 0.35498(17) 0.67073(19) 0.53053(15) 0.0295(5) Uani 1 1 d . . . . .
H27 H 0.3585 0.6346 0.4768 0.035 Uiso 1 1 calc R . . . .
C28 C 0.3086(2) 0.6482(2) 0.83673(14) 0.0327(5) Uani 1 1 d . . . . .
H28 H 0.3288 0.7146 0.8649 0.039 Uiso 1 1 calc R . . . .
C29 C 0.52181(18) 0.3190(2) 0.81369(14) 0.0303(5) Uani 1 1 d . . . . .
H29 H 0.5224 0.2681 0.8570 0.036 Uiso 1 1 calc R . . . .
C30 C 0.30060(19) 0.64406(19) 0.75263(13) 0.0281(5) Uani 1 1 d . . . . .
H30 H 0.3148 0.7079 0.7232 0.034 Uiso 1 1 calc R . . . .
C31 C 0.55861(18) 0.4248(2) 0.82990(13) 0.0297(5) Uani 1 1 d . . . . .
H31 H 0.5862 0.4463 0.8844 0.036 Uiso 1 1 calc R . . . .
C32 C 0.48423(18) 0.28761(18) 0.73417(14) 0.0289(5) Uani 1 1 d . . . . .
H32 H 0.4616 0.2142 0.7226 0.035 Uiso 1 1 calc R . . . .
C33 C 0.0865(2) 0.5077(2) 0.15513(14) 0.0343(5) Uani 1 1 d . . . . .
H33A H 0.0091 0.5198 0.1249 0.051 Uiso 1 1 calc GR . . . .
H33B H 0.0952 0.4306 0.1705 0.051 Uiso 1 1 calc GR . . . .
H33C H 0.1443 0.5273 0.1206 0.051 Uiso 1 1 calc GR . . . .
C34 C 0.2870(2) 0.5556(2) 0.87991(13) 0.0318(5) Uani 1 1 d . . . . .
H34 H 0.2925 0.5583 0.9377 0.038 Uiso 1 1 calc R . . . .
C35 C 0.44039(19) 0.7550(2) 0.53668(18) 0.0409(6) Uani 1 1 d . . . . .
H35A H 0.4311 0.8029 0.5834 0.049 Uiso 1 1 calc R . . . .
H35B H 0.4278 0.7999 0.4865 0.049 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 1.4204(14) . ?
S1 O2 1.4268(15) . ?
S1 N4 1.6857(16) . ?
S1 C5 1.758(2) . ?
O3 C11 1.202(2) . ?
N4 C11 1.411(3) . ?
N4 C27 1.472(3) . ?
C5 C6 1.390(3) . ?
C5 C17 1.388(3) . ?
C6 H6 0.9500 . ?
C6 C20 1.386(3) . ?
C7 C13 1.494(3) . ?
C7 C14 1.384(3) . ?
C7 C18 1.401(3) . ?
C8 C15 1.520(3) . ?
C8 C25 1.382(3) . ?
C8 C30 1.389(3) . ?
C9 C13 1.461(3) . ?
C9 C16 1.402(3) . ?
C9 C19 1.409(3) . ?
C10 C13 1.349(3) . ?
C10 C15 1.501(3) . ?
C10 C27 1.487(3) . ?
C11 C15 1.527(3) . ?
C12 C20 1.391(3) . ?
C12 C22 1.395(3) . ?
C12 C33 1.508(3) . ?
C14 H14 0.9500 . ?
C14 C32 1.388(3) . ?
C15 H15 1.0000 . ?
C16 H16 0.9500 . ?
C16 C26 1.378(3) . ?
C17 H17 0.9500 . ?
C17 C22 1.384(3) . ?
C18 H18 0.9500 . ?
C18 C31 1.380(3) . ?
C19 C21 1.395(3) . ?
C19 C35 1.488(3) . ?
C20 H20 0.9500 . ?
C21 H21 0.9500 . ?
C21 C23 1.384(3) . ?
C22 H22 0.9500 . ?
C23 H23 0.9500 . ?
C23 C26 1.388(3) . ?
C24 H24 0.9500 . ?
C24 C25 1.389(3) . ?
C24 C34 1.383(3) . ?
C25 H25 0.9500 . ?
C26 H26 0.9500 . ?
C27 H27 1.0000 . ?
C27 C35 1.431(3) . ?
C28 H28 0.9500 . ?
C28 C30 1.383(3) . ?
C28 C34 1.385(3) . ?
C29 H29 0.9500 . ?
C29 C31 1.381(3) . ?
C29 C32 1.380(3) . ?
C30 H30 0.9500 . ?
C31 H31 0.9500 . ?
C32 H32 0.9500 . ?
C33 H33A 0.9800 . ?
C33 H33B 0.9800 . ?
C33 H33C 0.9800 . ?
C34 H34 0.9500 . ?
C35 H35A 0.9900 . ?
C35 H35B 0.9900 . ?

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 120.23(9) . . ?
O1 S1 N4 106.94(8) . . ?
O1 S1 C5 110.19(9) . . ?
O2 S1 N4 105.64(8) . . ?
O2 S1 C5 108.84(9) . . ?
N4 S1 C5 103.64(9) . . ?
C11 N4 S1 122.44(13) . . ?
C11 N4 C27 111.77(16) . . ?
C27 N4 S1 122.24(14) . . ?
C6 C5 S1 119.46(16) . . ?
C17 C5 S1 119.02(15) . . ?
C17 C5 C6 121.51(19) . . ?
C5 C6 H6 120.5 . . ?
C20 C6 C5 118.90(19) . . ?
C20 C6 H6 120.5 . . ?
C14 C7 C13 121.05(18) . . ?
C14 C7 C18 118.58(19) . . ?
C18 C7 C13 119.99(19) . . ?
C25 C8 C15 120.59(19) . . ?
C25 C8 C30 119.10(19) . . ?
C30 C8 C15 120.21(18) . . ?
C16 C9 C13 122.15(19) . . ?
C16 C9 C19 118.91(19) . . ?
C19 C9 C13 118.94(18) . . ?
C13 C10 C15 127.79(18) . . ?
C13 C10 C27 121.34(18) . . ?
C27 C10 C15 110.65(16) . . ?
O3 C11 N4 126.37(18) . . ?
O3 C11 C15 125.34(19) . . ?
N4 C11 C15 108.29(16) . . ?
C20 C12 C22 118.8(2) . . ?
C20 C12 C33 120.96(19) . . ?
C22 C12 C33 120.2(2) . . ?
C9 C13 C7 122.03(17) . . ?
C10 C13 C7 119.28(17) . . ?
C10 C13 C9 118.65(18) . . ?
C7 C14 H14 119.8 . . ?
C7 C14 C32 120.5(2) . . ?
C32 C14 H14 119.8 . . ?
C8 C15 C11 111.70(16) . . ?
C8 C15 H15 109.1 . . ?
C10 C15 C8 114.04(16) . . ?
C10 C15 C11 103.64(16) . . ?
C10 C15 H15 109.1 . . ?
C11 C15 H15 109.1 . . ?
C9 C16 H16 119.5 . . ?
C26 C16 C9 121.0(2) . . ?
C26 C16 H16 119.5 . . ?
C5 C17 H17 120.7 . . ?
C22 C17 C5 118.52(19) . . ?
C22 C17 H17 120.7 . . ?
C7 C18 H18 119.7 . . ?
C31 C18 C7 120.5(2) . . ?
C31 C18 H18 119.7 . . ?
C9 C19 C35 119.26(19) . . ?
C21 C19 C9 119.19(19) . . ?
C21 C19 C35 121.5(2) . . ?
C6 C20 C12 120.91(19) . . ?
C6 C20 H20 119.5 . . ?
C12 C20 H20 119.5 . . ?
C19 C21 H21 119.5 . . ?
C23 C21 C19 121.0(2) . . ?
C23 C21 H21 119.5 . . ?
C12 C22 H22 119.3 . . ?
C17 C22 C12 121.3(2) . . ?
C17 C22 H22 119.3 . . ?
C21 C23 H23 120.1 . . ?
C21 C23 C26 119.83(19) . . ?
C26 C23 H23 120.1 . . ?
C25 C24 H24 120.0 . . ?
C34 C24 H24 120.0 . . ?
C34 C24 C25 119.9(2) . . ?
C8 C25 C24 120.6(2) . . ?
C8 C25 H25 119.7 . . ?
C24 C25 H25 119.7 . . ?
C16 C26 C23 120.08(19) . . ?
C16 C26 H26 120.0 . . ?
C23 C26 H26 120.0 . . ?
N4 C27 C10 103.93(16) . . ?
N4 C27 H27 105.1 . . ?
C10 C27 H27 105.1 . . ?
C35 C27 N4 122.2(2) . . ?
C35 C27 C10 113.78(19) . . ?
C35 C27 H27 105.1 . . ?
C30 C28 H28 120.0 . . ?
C30 C28 C34 120.0(2) . . ?
C34 C28 H28 120.0 . . ?
C31 C29 H29 120.2 . . ?
C32 C29 H29 120.2 . . ?
C32 C29 C31 119.6(2) . . ?
C8 C30 H30 119.7 . . ?
C28 C30 C8 120.6(2) . . ?
C28 C30 H30 119.7 . . ?
C18 C31 C29 120.4(2) . . ?
C18 C31 H31 119.8 . . ?
C29 C31 H31 119.8 . . ?
C14 C32 H32 119.8 . . ?
C29 C32 C14 120.4(2) . . ?
C29 C32 H32 119.8 . . ?
C12 C33 H33A 109.5 . . ?
C12 C33 H33B 109.5 . . ?
C12 C33 H33C 109.5 . . ?
H33A C33 H33B 109.5 . . ?
H33A C33 H33C 109.5 . . ?
H33B C33 H33C 109.5 . . ?
C24 C34 C28 119.8(2) . . ?
C24 C34 H34 120.1 . . ?
C28 C34 H34 120.1 . . ?
C19 C35 H35A 109.1 . . ?
C19 C35 H35B 109.1 . . ?
C27 C35 C19 112.7(2) . . ?
C27 C35 H35A 109.1 . . ?
C27 C35 H35B 109.1 . . ?
H35A C35 H35B 107.8 . . ?

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
S1 N4 C11 O3 -7.8(3) . . . . ?
S1 N4 C11 C15 171.70(13) . . . . ?
S1 N4 C27 C10 -172.75(14) . . . . ?
S1 N4 C27 C35 56.9(3) . . . . ?
S1 C5 C6 C20 179.58(15) . . . . ?
S1 C5 C17 C22 -178.15(15) . . . . ?
O1 S1 N4 C11 34.20(17) . . . . ?
O1 S1 N4 C27 -168.79(16) . . . . ?
O1 S1 C5 C6 141.55(16) . . . . ?
O1 S1 C5 C17 -39.61(18) . . . . ?
O2 S1 N4 C11 163.39(15) . . . . ?
O2 S1 N4 C27 -39.61(18) . . . . ?
O2 S1 C5 C6 7.75(19) . . . . ?
O2 S1 C5 C17 -173.41(15) . . . . ?
O3 C11 C15 C8 -63.3(3) . . . . ?
O3 C11 C15 C10 173.5(2) . . . . ?
N4 S1 C5 C6 -104.33(16) . . . . ?
N4 S1 C5 C17 74.51(17) . . . . ?
N4 C11 C15 C8 117.22(18) . . . . ?
N4 C11 C15 C10 -6.0(2) . . . . ?
N4 C27 C35 C19 171.0(2) . . . . ?
C5 S1 N4 C11 -82.22(17) . . . . ?
C5 S1 N4 C27 74.78(18) . . . . ?
C5 C6 C20 C12 -1.6(3) . . . . ?
C5 C17 C22 C12 -1.3(3) . . . . ?
C6 C5 C17 C22 0.7(3) . . . . ?
C7 C14 C32 C29 0.4(3) . . . . ?
C7 C18 C31 C29 1.6(3) . . . . ?
C9 C16 C26 C23 0.7(3) . . . . ?
C9 C19 C21 C23 0.9(3) . . . . ?
C9 C19 C35 C27 -32.8(3) . . . . ?
C10 C27 C35 C19 44.9(3) . . . . ?
C11 N4 C27 C10 -13.6(2) . . . . ?
C11 N4 C27 C35 -143.9(2) . . . . ?
C13 C7 C14 C32 -170.45(18) . . . . ?
C13 C7 C18 C31 169.56(18) . . . . ?
C13 C9 C16 C26 178.53(19) . . . . ?
C13 C9 C19 C21 -179.37(19) . . . . ?
C13 C9 C19 C35 2.7(3) . . . . ?
C13 C10 C15 C8 50.5(3) . . . . ?
C13 C10 C15 C11 172.1(2) . . . . ?
C13 C10 C27 N4 -165.58(19) . . . . ?
C13 C10 C27 C35 -30.4(3) . . . . ?
C14 C7 C13 C9 -117.0(2) . . . . ?
C14 C7 C13 C10 65.4(3) . . . . ?
C14 C7 C18 C31 -3.5(3) . . . . ?
C15 C8 C25 C24 175.62(18) . . . . ?
C15 C8 C30 C28 -175.35(19) . . . . ?
C15 C10 C13 C7 3.3(3) . . . . ?
C15 C10 C13 C9 -174.43(19) . . . . ?
C15 C10 C27 N4 9.4(2) . . . . ?
C15 C10 C27 C35 144.6(2) . . . . ?
C16 C9 C13 C7 17.5(3) . . . . ?
C16 C9 C13 C10 -164.8(2) . . . . ?
C16 C9 C19 C21 -0.2(3) . . . . ?
C16 C9 C19 C35 -178.1(2) . . . . ?
C17 C5 C6 C20 0.8(3) . . . . ?
C18 C7 C13 C9 70.1(3) . . . . ?
C18 C7 C13 C10 -107.6(2) . . . . ?
C18 C7 C14 C32 2.6(3) . . . . ?
C19 C9 C13 C7 -163.30(19) . . . . ?
C19 C9 C13 C10 14.4(3) . . . . ?
C19 C9 C16 C26 -0.6(3) . . . . ?
C19 C21 C23 C26 -0.8(3) . . . . ?
C20 C12 C22 C17 0.5(3) . . . . ?
C21 C19 C35 C27 149.3(2) . . . . ?
C21 C23 C26 C16 0.0(3) . . . . ?
C22 C12 C20 C6 1.0(3) . . . . ?
C25 C8 C15 C10 -125.5(2) . . . . ?
C25 C8 C15 C11 117.4(2) . . . . ?
C25 C8 C30 C28 0.9(3) . . . . ?
C25 C24 C34 C28 0.4(3) . . . . ?
C27 N4 C11 O3 -166.9(2) . . . . ?
C27 N4 C11 C15 12.5(2) . . . . ?
C27 C10 C13 C7 177.32(19) . . . . ?
C27 C10 C13 C9 -0.4(3) . . . . ?
C27 C10 C15 C8 -124.04(19) . . . . ?
C27 C10 C15 C11 -2.4(2) . . . . ?
C30 C8 C15 C10 50.7(3) . . . . ?
C30 C8 C15 C11 -66.4(2) . . . . ?
C30 C8 C25 C24 -0.6(3) . . . . ?
C30 C28 C34 C24 -0.1(3) . . . . ?
C31 C29 C32 C14 -2.4(3) . . . . ?
C32 C29 C31 C18 1.4(3) . . . . ?
C33 C12 C20 C6 -178.02(19) . . . . ?
C33 C12 C22 C17 179.52(19) . . . . ?
C34 C24 C25 C8 0.0(3) . . . . ?
C34 C28 C30 C8 -0.5(3) . . . . ?
C35 C19 C21 C23 178.8(2) . . . . ?

_olex2_date_sample_data_collection 2015-08-24
_olex2_submission_special_instructions 'No special instructions were received'
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: hexane and ethyl acetate'
