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

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

data_mjh120026
_database_code_depnum_ccdc_archive 'CCDC 952229'
_audit_update_record             
;
2014-12-18 deposited with the CCDC.
2015-01-16 downloaded from the CCDC.
;
_audit_creation_date             2014-12-17
_audit_creation_method           
;
Olex2 1.2-alpha
(compiled 2014.12.09 svn.r3114 for OlexSys, GUI svn.r4963)
;
_shelxl_version_number           2014/6
_chemical_name_common            ?
_chemical_name_systematic        
(3aS*,5S*,10bS*)-5-(hydroxy(o-tolyl)amino)-10-tosyl-4,5,10,10b-tetrahydropyrrolo[3,4-a]carbazole-1,3(2H,3aH)-dione
_chemical_formula_moiety         'C28 H25 N3 O5 S, C H Cl3'
_chemical_formula_sum            'C29 H26 Cl3 N3 O5 S'
_chemical_formula_weight         634.94
_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'
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'
N N 0.0311 0.0180 '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'

_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                   10.0614(5)
_cell_length_b                   10.2208(5)
_cell_length_c                   15.2649(7)
_cell_angle_alpha                104.231(4)
_cell_angle_beta                 95.071(4)
_cell_angle_gamma                109.240(4)
_cell_volume                     1411.79(12)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    7995
_cell_measurement_temperature    150.0
_cell_measurement_theta_max      66.8641
_cell_measurement_theta_min      3.0366
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    4.017
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.86739
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET)
(compiled Jan 23 2012,18:06:46)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_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    1.494
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             656
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.12
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0264
_diffrn_reflns_av_unetI/netI     0.0239
_diffrn_reflns_Laue_measured_fraction_full 0.971
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            13047
_diffrn_reflns_point_group_measured_fraction_full 0.971
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         66.970
_diffrn_reflns_theta_min         3.039
_diffrn_ambient_temperature      150.0
_diffrn_detector_area_resol_mean 10.3968
_diffrn_measured_fraction_theta_full 0.971
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega   19.00  107.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       40.3405   38.0000   90.0000 88

#__ type_ start__ end____ width___ exp.time_
  2 omega    7.00   85.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       40.3405 -125.0000 -150.0000 78

#__ type_ start__ end____ width___ exp.time_
  3 omega  -33.00   67.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       40.3405  -38.0000  -90.0000 100

#__ type_ start__ end____ width___ exp.time_
  4 omega -117.00  -91.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      -83.0000  125.0000 -180.0000 26

#__ type_ start__ end____ width___ exp.time_
  5 omega   59.00  127.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000  -90.0000   20.0000 68

#__ type_ start__ end____ width___ exp.time_
  6 omega   64.00  139.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000   15.0000   60.0000 75

#__ type_ start__ end____ width___ exp.time_
  7 omega   57.00   83.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000  -90.0000  175.0000 26

#__ type_ start__ end____ width___ exp.time_
  8 omega   16.00   56.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000  -77.0000  -60.0000 40

#__ type_ start__ end____ width___ exp.time_
  9 omega   28.00   56.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000  -90.0000   20.0000 28

#__ type_ start__ end____ width___ exp.time_
 10 omega   25.00   72.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000  -45.0000 -180.0000 47

#__ type_ start__ end____ width___ exp.time_
 11 omega   18.00   69.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000  -30.0000  -90.0000 51

#__ type_ start__ end____ width___ exp.time_
 12 omega   20.00   76.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000  -45.0000    0.0000 56

#__ type_ start__ end____ width___ exp.time_
 13 omega   22.00   61.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000  -61.0000 -120.0000 39

#__ type_ start__ end____ width___ exp.time_
 14 omega   23.00   63.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000  -30.0000  120.0000 40

#__ type_ start__ end____ width___ exp.time_
 15 omega   21.00   47.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000  -94.0000 -120.0000 26

#__ type_ start__ end____ width___ exp.time_
 16 omega  118.00  146.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000   30.0000  -90.0000 28

#__ type_ start__ end____ width___ exp.time_
 17 omega   20.00   92.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000  -58.0000   87.0000 72

#__ type_ start__ end____ width___ exp.time_
 18 omega   56.00   81.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000  -94.0000 -120.0000 25

#__ type_ start__ end____ width___ exp.time_
 19 omega   28.00   53.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000  -30.0000   60.0000 25

#__ type_ start__ end____ width___ exp.time_
 20 omega   60.00   89.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000  -77.0000  -60.0000 29

#__ type_ start__ end____ width___ exp.time_
 21 omega   16.00   69.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000  -30.0000 -150.0000 53

#__ type_ start__ end____ width___ exp.time_
 22 omega   50.00   75.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000  -45.0000  -30.0000 25

#__ type_ start__ end____ width___ exp.time_
 23 omega   88.00  114.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000  -90.0000  175.0000 26

#__ type_ start__ end____ width___ exp.time_
 24 omega   48.00   74.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000   15.0000  150.0000 26

#__ type_ start__ end____ width___ exp.time_
 25 omega   81.00  169.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000   15.0000  150.0000 88

#__ type_ start__ end____ width___ exp.time_
 26 omega   22.00   68.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000  -77.0000   90.0000 46

#__ type_ start__ end____ width___ exp.time_
 27 omega   72.00   97.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000  -77.0000   90.0000 25

#__ type_ start__ end____ width___ exp.time_
 28 omega   52.00  116.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000  -92.0000  -69.0000 64

#__ type_ start__ end____ width___ exp.time_
 29 omega   42.00   67.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000  -77.0000  -30.0000 25

#__ type_ start__ end____ width___ exp.time_
 30 omega  102.00  127.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000  -77.0000  -30.0000 25

#__ type_ start__ end____ width___ exp.time_
 31 omega   28.00   53.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000 -125.0000 -120.0000 25

#__ type_ start__ end____ width___ exp.time_
 32 omega   59.00   85.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000  -61.0000 -180.0000 26

#__ type_ start__ end____ width___ exp.time_
 33 omega   97.00  124.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000  -92.0000   91.0000 27
;
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini ultra'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.1053722000
_diffrn_orient_matrix_UB_12      -0.0253532000
_diffrn_orient_matrix_UB_13      0.0668680000
_diffrn_orient_matrix_UB_21      0.0620975000
_diffrn_orient_matrix_UB_22      -0.1064905000
_diffrn_orient_matrix_UB_23      0.0272736000
_diffrn_orient_matrix_UB_31      0.1107894000
_diffrn_orient_matrix_UB_32      0.1260378000
_diffrn_orient_matrix_UB_33      0.0775224000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   'Enhance Ultra (Cu) X-ray Source'
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4523
_reflns_number_total             4955
_reflns_odcompleteness_completeness 99.46
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.49
_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 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET)
(compiled Jan 23 2012,18:06:46)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET)
(compiled Jan 23 2012,18:06:46)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET)
(compiled Jan 23 2012,18:06:46)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XS (Sheldrick, 2008)'
_refine_diff_density_max         0.934
_refine_diff_density_min         -0.686
_refine_diff_density_rms         0.065
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     397
_refine_ls_number_reflns         4955
_refine_ls_number_restraints     411
_refine_ls_R_factor_all          0.0537
_refine_ls_R_factor_gt           0.0490
_refine_ls_restrained_S_all      1.041
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0628P)²+1.8642P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1265
_refine_ls_wR_factor_ref         0.1296
_refine_special_details          
;
There is a disordered Chloroform molecule in the
 structure, the occupancies have been fixed to give
 unit total occupancy at values of those close to
 free refinement of the Cl atoms. The structure
 could be squeezed, but the solvent molecule has
 been left in for completeness, however moderate
 restraints on Cl C distances were required to reach
 refinement convergence.
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2. Restrained distances
 Cl1S-C1S \\sim Cl1P-C1P \\sim Cl1T-C1T \\sim Cl3T-C1T \\sim Cl2T-C1T \\sim
Cl2S-C1S \\sim Cl2P-C1P ~
 Cl3S-C1S \\sim Cl3P-C1P
 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
Uanis(C1P) = Uanis(C1S) = Uanis(C1T)
Uanis(Cl3P) = Uanis(Cl3S) = Uanis(Cl3T)
Uanis(Cl1T) = Uanis(Cl1P) = Uanis(Cl1S)
Uanis(Cl2T) = Uanis(Cl2S) = Uanis(Cl2P)
4. Rigid body (RIGU) restrains
 All non-hydrogen atoms
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
5. Others
 Fixed Sof: C1P(0.65) H1P(0.65) Cl3P(0.65) Cl2P(0.65) Cl1P(0.65) C1S(0.25)
 H1S(0.25) Cl3S(0.25) Cl1S(0.25) Cl2S(0.25) C1T(0.1) H1T(0.1) Cl2T(0.1)
 Cl1T(0.1) Cl3T(0.1)
6.a Ternary CH refined with riding coordinates:
 C8(H8), C10(H10), C13(H13), C1P(H1P), C1S(H1S), C1T(H1T)
6.b Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B)
6.c Aromatic/amide H refined with riding coordinates:
 N2(H2), C2(H2A), C0AA(H0AA), C4(H4), C5(H5), C16(H16), C17(H17), C18(H18),
 C19(H19), C23(H23), C24(H24), C26(H26), C27(H27)
6.d Idealised Me refined as rotating group:
 C21(H21A,H21B,H21C), C28(H28A,H28B,H28C)
6.e Idealised tetrahedral OH refined as rotating group:
 O3(H3)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_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 0.29026(6) 0.33820(6) 0.85351(4) 0.02107(16) Uani 1 1 d . U . . .
O0AA O 0.91089(18) 0.3071(2) 1.04995(12) 0.0301(4) Uani 1 1 d . U . . .
O2 O 0.43023(17) 0.08752(19) 0.93814(12) 0.0279(4) Uani 1 1 d . U . . .
O3 O 0.82618(18) 0.54595(17) 0.81553(11) 0.0247(4) Uani 1 1 d . U . . .
H3 H 0.9057 0.5955 0.8504 0.037 Uiso 1 1 calc GR . . . .
O4 O 0.34750(18) 0.37051(19) 0.94843(12) 0.0264(4) Uani 1 1 d . U . . .
O6 O 0.14199(17) 0.25446(18) 0.81924(13) 0.0276(4) Uani 1 1 d . U . . .
N1 N 0.38259(19) 0.2494(2) 0.79409(13) 0.0199(4) Uani 1 1 d . U . . .
N2 N 0.6682(2) 0.1764(2) 1.00692(13) 0.0232(4) Uani 1 1 d . U . . .
H2 H 0.6627 0.1156 1.0397 0.028 Uiso 1 1 calc R . . . .
N3 N 0.8423(2) 0.4334(2) 0.74316(13) 0.0201(4) Uani 1 1 d . U . . .
C1 C 0.3555(2) 0.2105(2) 0.69637(16) 0.0200(5) Uani 1 1 d . U . . .
C2 C 0.2265(3) 0.1648(3) 0.63517(18) 0.0272(5) Uani 1 1 d . U . . .
H2A H 0.1396 0.1603 0.6564 0.033 Uiso 1 1 calc R . . . .
C0AA C 0.2307(3) 0.1266(3) 0.54262(18) 0.0312(6) Uani 1 1 d . U . . .
H0AA H 0.1451 0.0970 0.4991 0.037 Uiso 1 1 calc R . . . .
C4 C 0.3578(3) 0.1303(3) 0.51122(17) 0.0299(6) Uani 1 1 d . U . . .
H4 H 0.3565 0.1009 0.4470 0.036 Uiso 1 1 calc R . . . .
C5 C 0.4854(3) 0.1763(3) 0.57217(16) 0.0244(5) Uani 1 1 d . U . . .
H5 H 0.5716 0.1788 0.5504 0.029 Uiso 1 1 calc R . . . .
C6 C 0.4850(2) 0.2188(2) 0.66637(16) 0.0194(5) Uani 1 1 d . U . . .
C7 C 0.5949(2) 0.2674(2) 0.74764(15) 0.0179(4) Uani 1 1 d . U . . .
C8 C 0.7519(2) 0.2918(2) 0.75423(15) 0.0184(4) Uani 1 1 d . U . . .
H8 H 0.7603 0.2139 0.7031 0.022 Uiso 1 1 calc R . . . .
C9 C 0.8106(2) 0.2732(3) 0.84410(16) 0.0206(5) Uani 1 1 d . U . . .
H9A H 0.9166 0.3115 0.8534 0.025 Uiso 1 1 calc R . . . .
H9B H 0.7792 0.1683 0.8380 0.025 Uiso 1 1 calc R . . . .
C10 C 0.7649(2) 0.3484(3) 0.93071(15) 0.0195(5) Uani 1 1 d . U . . .
H10 H 0.8177 0.4556 0.9505 0.023 Uiso 1 1 calc R . . . .
C11 C 0.7954(2) 0.2810(3) 1.00427(15) 0.0224(5) Uani 1 1 d . U . . .
C12 C 0.5505(2) 0.1766(3) 0.95303(15) 0.0210(5) Uani 1 1 d . U . . .
C13 C 0.6015(2) 0.3099(2) 0.91857(15) 0.0187(5) Uani 1 1 d . U . . .
H13 H 0.5812 0.3908 0.9599 0.022 Uiso 1 1 calc R . . . .
C14 C 0.5322(2) 0.2833(2) 0.82208(15) 0.0179(4) Uani 1 1 d . U . . .
C15 C 0.8002(2) 0.4531(2) 0.65575(16) 0.0212(5) Uani 1 1 d . U . . .
C16 C 0.7173(3) 0.5366(3) 0.64789(18) 0.0270(5) Uani 1 1 d . U . . .
H16 H 0.6862 0.5803 0.7005 0.032 Uiso 1 1 calc R . . . .
C17 C 0.6800(3) 0.5562(3) 0.56377(19) 0.0345(6) Uani 1 1 d . U . . .
H17 H 0.6237 0.6136 0.5588 0.041 Uiso 1 1 calc R . . . .
C18 C 0.7248(3) 0.4921(3) 0.48711(19) 0.0382(6) Uani 1 1 d . U . . .
H18 H 0.6992 0.5047 0.4292 0.046 Uiso 1 1 calc R . . . .
C19 C 0.8069(3) 0.4097(3) 0.49539(18) 0.0336(6) Uani 1 1 d . U . . .
H19 H 0.8377 0.3667 0.4424 0.040 Uiso 1 1 calc R . . . .
C20 C 0.8465(3) 0.3874(3) 0.57873(17) 0.0258(5) Uani 1 1 d . U . . .
C21 C 0.9338(3) 0.2935(3) 0.58211(19) 0.0332(6) Uani 1 1 d . U . . .
H21A H 0.9903 0.3233 0.6441 0.050 Uiso 1 1 calc GR . . . .
H21B H 0.9982 0.3042 0.5377 0.050 Uiso 1 1 calc GR . . . .
H21C H 0.8696 0.1920 0.5668 0.050 Uiso 1 1 calc GR . . . .
C22 C 0.3306(3) 0.4989(3) 0.82087(17) 0.0236(5) Uani 1 1 d . U . . .
C23 C 0.2179(3) 0.5288(3) 0.78211(16) 0.0250(5) Uani 1 1 d . U . . .
H23 H 0.1217 0.4659 0.7759 0.030 Uiso 1 1 calc R . . . .
C24 C 0.2476(3) 0.6516(3) 0.75267(17) 0.0322(6) Uani 1 1 d . U . . .
H24 H 0.1708 0.6731 0.7268 0.039 Uiso 1 1 calc R . . . .
C25 C 0.3876(3) 0.7438(3) 0.76032(19) 0.0367(6) Uani 1 1 d . U . . .
C26 C 0.4979(3) 0.7124(3) 0.8014(2) 0.0438(7) Uani 1 1 d . U . . .
H26 H 0.5941 0.7757 0.8083 0.053 Uiso 1 1 calc R . . . .
C27 C 0.4715(3) 0.5914(3) 0.8324(2) 0.0368(6) Uani 1 1 d . U . . .
H27 H 0.5479 0.5723 0.8610 0.044 Uiso 1 1 calc R . . . .
C28 C 0.4198(5) 0.8734(3) 0.7239(2) 0.0533(9) Uani 1 1 d . U . . .
H28A H 0.4015 0.8406 0.6565 0.080 Uiso 1 1 calc GR . . . .
H28B H 0.5205 0.9365 0.7466 0.080 Uiso 1 1 calc GR . . . .
H28C H 0.3583 0.9273 0.7448 0.080 Uiso 1 1 calc GR . . . .
C1P C 0.0522(5) 0.0307(6) 0.1605(4) 0.0508(11) Uani 0.65 1 d D U P A 1
H1P H 0.0171 -0.0766 0.1317 0.061 Uiso 0.65 1 calc R . P A 1
Cl3P Cl 0.15426(15) 0.10423(18) 0.08842(9) 0.0587(3) Uani 0.65 1 d D U P A 1
Cl2P Cl 0.1544(3) 0.0629(4) 0.2718(4) 0.0473(6) Uani 0.65 1 d D U P A 1
Cl1P Cl -0.1025(2) 0.0724(3) 0.1704(3) 0.0645(5) Uani 0.65 1 d D U P A 1
C1S C 0.0627(11) 0.1178(15) 0.2029(8) 0.0508(11) Uani 0.25 1 d D U P B 2
H1S H 0.1120 0.2249 0.2162 0.061 Uiso 0.25 1 calc R . P B 2
Cl3S Cl 0.0939(4) 0.0311(5) 0.0997(3) 0.0587(3) Uani 0.25 1 d D U P B 2
Cl1S Cl -0.1131(7) 0.0794(8) 0.2128(4) 0.0645(5) Uani 0.25 1 d D U P B 2
Cl2S Cl 0.1276(13) 0.0614(13) 0.2899(7) 0.0473(6) Uani 0.25 1 d D U P B 2
C1T C 0.042(3) 0.130(4) 0.2656(12) 0.0508(11) Uani 0.1 1 d D U P C 3
H1T H 0.1033 0.2324 0.2714 0.061 Uiso 0.1 1 calc R . P C 3
Cl2T Cl 0.187(2) 0.079(2) 0.280(2) 0.0473(6) Uani 0.1 1 d D U P C 3
Cl1T Cl -0.0683(17) 0.1152(19) 0.1707(17) 0.0645(5) Uani 0.1 1 d D U P C 3
Cl3T Cl -0.0283(9) 0.1795(11) 0.3621(6) 0.0587(3) Uani 0.1 1 d D U P C 3


_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 O4 1.4255(18) . ?
S1 O6 1.4255(18) . ?
S1 N1 1.6762(19) . ?
S1 C22 1.763(2) . ?
O0AA C11 1.211(3) . ?
O2 C12 1.211(3) . ?
O3 H3 0.8400 . ?
O3 N3 1.449(2) . ?
N1 C1 1.422(3) . ?
N1 C14 1.427(3) . ?
N2 H2 0.8800 . ?
N2 C11 1.383(3) . ?
N2 C12 1.382(3) . ?
N3 C8 1.493(3) . ?
N3 C15 1.445(3) . ?
C1 C2 1.395(3) . ?
C1 C6 1.402(3) . ?
C2 H2A 0.9500 . ?
C2 C0AA 1.378(4) . ?
C0AA H0AA 0.9500 . ?
C0AA C4 1.397(4) . ?
C4 H4 0.9500 . ?
C4 C5 1.383(3) . ?
C5 H5 0.9500 . ?
C5 C6 1.397(3) . ?
C6 C7 1.449(3) . ?
C7 C8 1.506(3) . ?
C7 C14 1.349(3) . ?
C8 H8 1.0000 . ?
C8 C9 1.525(3) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C9 C10 1.547(3) . ?
C10 H10 1.0000 . ?
C10 C11 1.513(3) . ?
C10 C13 1.541(3) . ?
C12 C13 1.529(3) . ?
C13 H13 1.0000 . ?
C13 C14 1.492(3) . ?
C15 C16 1.392(3) . ?
C15 C20 1.402(3) . ?
C16 H16 0.9500 . ?
C16 C17 1.386(4) . ?
C17 H17 0.9500 . ?
C17 C18 1.383(4) . ?
C18 H18 0.9500 . ?
C18 C19 1.379(4) . ?
C19 H19 0.9500 . ?
C19 C20 1.393(4) . ?
C20 C21 1.506(4) . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
C22 C23 1.389(4) . ?
C22 C27 1.387(4) . ?
C23 H23 0.9500 . ?
C23 C24 1.386(4) . ?
C24 H24 0.9500 . ?
C24 C25 1.389(4) . ?
C25 C26 1.392(5) . ?
C25 C28 1.510(4) . ?
C26 H26 0.9500 . ?
C26 C27 1.385(4) . ?
C27 H27 0.9500 . ?
C28 H28A 0.9800 . ?
C28 H28B 0.9800 . ?
C28 H28C 0.9800 . ?
C1P H1P 1.0000 . ?
C1P Cl3P 1.711(5) . ?
C1P Cl2P 1.801(8) . ?
C1P Cl1P 1.754(5) . ?
C1S H1S 1.0000 . ?
C1S Cl3S 1.717(11) . ?
C1S Cl1S 1.711(10) . ?
C1S Cl2S 1.730(12) . ?
C1T H1T 1.0000 . ?
C1T Cl2T 1.716(14) . ?
C1T Cl1T 1.688(14) . ?
C1T Cl3T 1.728(14) . ?

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
O4 S1 N1 106.63(10) . . ?
O4 S1 C22 110.32(11) . . ?
O6 S1 O4 119.80(11) . . ?
O6 S1 N1 107.11(10) . . ?
O6 S1 C22 107.82(11) . . ?
N1 S1 C22 104.00(10) . . ?
N3 O3 H3 109.5 . . ?
C1 N1 S1 119.68(15) . . ?
C1 N1 C14 106.58(18) . . ?
C14 N1 S1 122.85(15) . . ?
C11 N2 H2 123.3 . . ?
C12 N2 H2 123.3 . . ?
C12 N2 C11 113.4(2) . . ?
O3 N3 C8 106.84(16) . . ?
C15 N3 O3 108.31(17) . . ?
C15 N3 C8 113.39(17) . . ?
C2 C1 N1 129.6(2) . . ?
C2 C1 C6 122.3(2) . . ?
C6 C1 N1 108.11(19) . . ?
C1 C2 H2A 121.4 . . ?
C0AA C2 C1 117.1(2) . . ?
C0AA C2 H2A 121.4 . . ?
C2 C0AA H0AA 119.2 . . ?
C2 C0AA C4 121.6(2) . . ?
C4 C0AA H0AA 119.2 . . ?
C0AA C4 H4 119.5 . . ?
C5 C4 C0AA 121.0(2) . . ?
C5 C4 H4 119.5 . . ?
C4 C5 H5 120.7 . . ?
C4 C5 C6 118.6(2) . . ?
C6 C5 H5 120.7 . . ?
C1 C6 C7 107.2(2) . . ?
C5 C6 C1 119.3(2) . . ?
C5 C6 C7 133.3(2) . . ?
C6 C7 C8 129.0(2) . . ?
C14 C7 C6 108.1(2) . . ?
C14 C7 C8 122.8(2) . . ?
N3 C8 C7 114.79(18) . . ?
N3 C8 H8 107.0 . . ?
N3 C8 C9 110.35(18) . . ?
C7 C8 H8 107.0 . . ?
C7 C8 C9 110.34(18) . . ?
C9 C8 H8 107.0 . . ?
C8 C9 H9A 108.5 . . ?
C8 C9 H9B 108.5 . . ?
C8 C9 C10 115.24(18) . . ?
H9A C9 H9B 107.5 . . ?
C10 C9 H9A 108.5 . . ?
C10 C9 H9B 108.5 . . ?
C9 C10 H10 111.5 . . ?
C11 C10 C9 106.19(18) . . ?
C11 C10 H10 111.5 . . ?
C11 C10 C13 103.17(18) . . ?
C13 C10 C9 112.54(18) . . ?
C13 C10 H10 111.5 . . ?
O0AA C11 N2 125.3(2) . . ?
O0AA C11 C10 127.0(2) . . ?
N2 C11 C10 107.64(18) . . ?
O2 C12 N2 125.3(2) . . ?
O2 C12 C13 127.7(2) . . ?
N2 C12 C13 107.00(19) . . ?
C10 C13 H13 109.0 . . ?
C12 C13 C10 103.10(18) . . ?
C12 C13 H13 109.0 . . ?
C14 C13 C10 113.27(18) . . ?
C14 C13 C12 113.17(18) . . ?
C14 C13 H13 109.0 . . ?
N1 C14 C13 123.73(19) . . ?
C7 C14 N1 109.97(19) . . ?
C7 C14 C13 125.7(2) . . ?
C16 C15 N3 121.2(2) . . ?
C16 C15 C20 120.5(2) . . ?
C20 C15 N3 118.3(2) . . ?
C15 C16 H16 119.8 . . ?
C17 C16 C15 120.4(2) . . ?
C17 C16 H16 119.8 . . ?
C16 C17 H17 120.1 . . ?
C18 C17 C16 119.8(3) . . ?
C18 C17 H17 120.1 . . ?
C17 C18 H18 120.3 . . ?
C19 C18 C17 119.5(2) . . ?
C19 C18 H18 120.3 . . ?
C18 C19 H19 118.8 . . ?
C18 C19 C20 122.3(3) . . ?
C20 C19 H19 118.8 . . ?
C15 C20 C21 123.2(2) . . ?
C19 C20 C15 117.5(2) . . ?
C19 C20 C21 119.3(2) . . ?
C20 C21 H21A 109.5 . . ?
C20 C21 H21B 109.5 . . ?
C20 C21 H21C 109.5 . . ?
H21A C21 H21B 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C23 C22 S1 118.19(19) . . ?
C27 C22 S1 120.7(2) . . ?
C27 C22 C23 121.1(2) . . ?
C22 C23 H23 120.5 . . ?
C24 C23 C22 119.1(2) . . ?
C24 C23 H23 120.5 . . ?
C23 C24 H24 119.4 . . ?
C23 C24 C25 121.2(3) . . ?
C25 C24 H24 119.4 . . ?
C24 C25 C26 118.1(3) . . ?
C24 C25 C28 121.1(3) . . ?
C26 C25 C28 120.8(3) . . ?
C25 C26 H26 119.0 . . ?
C27 C26 C25 121.9(3) . . ?
C27 C26 H26 119.0 . . ?
C22 C27 H27 120.8 . . ?
C26 C27 C22 118.4(3) . . ?
C26 C27 H27 120.8 . . ?
C25 C28 H28A 109.5 . . ?
C25 C28 H28B 109.5 . . ?
C25 C28 H28C 109.5 . . ?
H28A C28 H28B 109.5 . . ?
H28A C28 H28C 109.5 . . ?
H28B C28 H28C 109.5 . . ?
Cl3P C1P H1P 105.4 . . ?
Cl3P C1P Cl2P 113.2(3) . . ?
Cl3P C1P Cl1P 115.2(3) . . ?
Cl2P C1P H1P 105.4 . . ?
Cl1P C1P H1P 105.4 . . ?
Cl1P C1P Cl2P 111.3(3) . . ?
Cl3S C1S H1S 109.5 . . ?
Cl3S C1S Cl2S 109.8(7) . . ?
Cl1S C1S H1S 109.5 . . ?
Cl1S C1S Cl3S 116.1(7) . . ?
Cl1S C1S Cl2S 102.3(7) . . ?
Cl2S C1S H1S 109.5 . . ?
Cl2T C1T H1T 93.2 . . ?
Cl2T C1T Cl3T 116.9(17) . . ?
Cl1T C1T H1T 93.2 . . ?
Cl1T C1T Cl2T 132.4(15) . . ?
Cl1T C1T Cl3T 109.7(13) . . ?
Cl3T C1T H1T 93.2 . . ?

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 N1 C1 C2 -36.5(3) . . . . ?
S1 N1 C1 C6 146.02(16) . . . . ?
S1 N1 C14 C7 -143.68(17) . . . . ?
S1 N1 C14 C13 44.8(3) . . . . ?
S1 C22 C23 C24 -177.49(18) . . . . ?
S1 C22 C27 C26 176.7(2) . . . . ?
O2 C12 C13 C10 -161.4(2) . . . . ?
O2 C12 C13 C14 -38.6(3) . . . . ?
O3 N3 C8 C7 59.7(2) . . . . ?
O3 N3 C8 C9 -65.8(2) . . . . ?
O3 N3 C15 C16 -18.3(3) . . . . ?
O3 N3 C15 C20 160.86(19) . . . . ?
O4 S1 N1 C1 -176.03(17) . . . . ?
O4 S1 N1 C14 -36.6(2) . . . . ?
O4 S1 C22 C23 -123.58(19) . . . . ?
O4 S1 C22 C27 57.4(2) . . . . ?
O6 S1 N1 C1 54.57(19) . . . . ?
O6 S1 N1 C14 -166.04(18) . . . . ?
O6 S1 C22 C23 8.9(2) . . . . ?
O6 S1 C22 C27 -170.1(2) . . . . ?
N1 S1 C22 C23 122.42(19) . . . . ?
N1 S1 C22 C27 -56.6(2) . . . . ?
N1 C1 C2 C0AA -176.7(2) . . . . ?
N1 C1 C6 C5 175.8(2) . . . . ?
N1 C1 C6 C7 -1.4(2) . . . . ?
N2 C12 C13 C10 19.6(2) . . . . ?
N2 C12 C13 C14 142.33(19) . . . . ?
N3 C8 C9 C10 82.7(2) . . . . ?
N3 C15 C16 C17 178.9(2) . . . . ?
N3 C15 C20 C19 -178.9(2) . . . . ?
N3 C15 C20 C21 2.1(3) . . . . ?
C1 N1 C14 C7 0.2(2) . . . . ?
C1 N1 C14 C13 -171.3(2) . . . . ?
C1 C2 C0AA C4 1.3(4) . . . . ?
C1 C6 C7 C8 178.8(2) . . . . ?
C1 C6 C7 C14 1.5(2) . . . . ?
C2 C1 C6 C5 -1.9(3) . . . . ?
C2 C1 C6 C7 -179.1(2) . . . . ?
C2 C0AA C4 C5 -1.6(4) . . . . ?
C0AA C4 C5 C6 0.2(4) . . . . ?
C4 C5 C6 C1 1.5(3) . . . . ?
C4 C5 C6 C7 177.9(2) . . . . ?
C5 C6 C7 C8 2.2(4) . . . . ?
C5 C6 C7 C14 -175.1(2) . . . . ?
C6 C1 C2 C0AA 0.4(4) . . . . ?
C6 C7 C8 N3 81.1(3) . . . . ?
C6 C7 C8 C9 -153.5(2) . . . . ?
C6 C7 C14 N1 -1.0(2) . . . . ?
C6 C7 C14 C13 170.2(2) . . . . ?
C7 C8 C9 C10 -45.3(3) . . . . ?
C8 N3 C15 C16 100.1(2) . . . . ?
C8 N3 C15 C20 -80.7(3) . . . . ?
C8 C7 C14 N1 -178.53(19) . . . . ?
C8 C7 C14 C13 -7.3(4) . . . . ?
C8 C9 C10 C11 163.43(19) . . . . ?
C8 C9 C10 C13 51.3(3) . . . . ?
C9 C10 C11 O0AA 77.9(3) . . . . ?
C9 C10 C11 N2 -98.6(2) . . . . ?
C9 C10 C13 C12 90.7(2) . . . . ?
C9 C10 C13 C14 -31.9(3) . . . . ?
C10 C13 C14 N1 -178.47(19) . . . . ?
C10 C13 C14 C7 11.4(3) . . . . ?
C11 N2 C12 O2 173.2(2) . . . . ?
C11 N2 C12 C13 -7.7(3) . . . . ?
C11 C10 C13 C12 -23.3(2) . . . . ?
C11 C10 C13 C14 -145.98(19) . . . . ?
C12 N2 C11 O0AA 175.3(2) . . . . ?
C12 N2 C11 C10 -8.1(3) . . . . ?
C12 C13 C14 N1 64.6(3) . . . . ?
C12 C13 C14 C7 -105.5(3) . . . . ?
C13 C10 C11 O0AA -163.6(2) . . . . ?
C13 C10 C11 N2 19.9(2) . . . . ?
C14 N1 C1 C2 178.2(2) . . . . ?
C14 N1 C1 C6 0.8(2) . . . . ?
C14 C7 C8 N3 -102.0(2) . . . . ?
C14 C7 C8 C9 23.5(3) . . . . ?
C15 N3 C8 C7 -59.6(2) . . . . ?
C15 N3 C8 C9 175.01(18) . . . . ?
C15 C16 C17 C18 0.2(4) . . . . ?
C16 C15 C20 C19 0.3(3) . . . . ?
C16 C15 C20 C21 -178.8(2) . . . . ?
C16 C17 C18 C19 -0.3(4) . . . . ?
C17 C18 C19 C20 0.4(4) . . . . ?
C18 C19 C20 C15 -0.4(4) . . . . ?
C18 C19 C20 C21 178.7(3) . . . . ?
C20 C15 C16 C17 -0.2(4) . . . . ?
C22 S1 N1 C1 -59.42(19) . . . . ?
C22 S1 N1 C14 80.0(2) . . . . ?
C22 C23 C24 C25 0.7(4) . . . . ?
C23 C22 C27 C26 -2.3(4) . . . . ?
C23 C24 C25 C26 -2.1(4) . . . . ?
C23 C24 C25 C28 176.9(2) . . . . ?
C24 C25 C26 C27 1.4(4) . . . . ?
C25 C26 C27 C22 0.8(5) . . . . ?
C27 C22 C23 C24 1.5(4) . . . . ?
C28 C25 C26 C27 -177.7(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_mjh80
_database_code_depnum_ccdc_archive 'CCDC 952356'
_audit_update_record             
;
2014-12-18 deposited with the CCDC.
2015-01-16 downloaded from the CCDC.
;
_audit_creation_date             2014-12-17
_audit_creation_method           
;
Olex2 1.2-alpha
(compiled 2014.12.09 svn.r3114 for OlexSys, GUI svn.r4963)
;
_shelxl_version_number           2014/6
_chemical_name_common            ?
_chemical_name_systematic        
(3aS*,10aS*,10bS*)-2-methyl-10-tosyl-4,10,10a,10b-tetrahydropyrrolo[3,4-a]carbazole-1,3(2H,3aH)-dione
_chemical_formula_moiety         'C22 H20 N2 O4 S'
_chemical_formula_sum            'C22 H20 N2 O4 S'
_chemical_formula_weight         408.46
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C22 H20 N2 O4 S'
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'

_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                   10.5141(8)
_cell_length_b                   17.9454(11)
_cell_length_c                   11.0976(8)
_cell_angle_alpha                90
_cell_angle_beta                 113.865(9)
_cell_angle_gamma                90
_cell_volume                     1914.9(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3401
_cell_measurement_temperature    150.0
_cell_measurement_theta_max      28.3943
_cell_measurement_theta_min      3.0242
_shelx_estimated_absorpt_T_max   0.942
_shelx_estimated_absorpt_T_min   0.942
_exptl_absorpt_coefficient_mu    0.202
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.94843
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.34.49 (release 20-01-2011 CrysAlis171 .NET)
(compiled Jan 20 2011,15:58:25)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.417
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             856
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.3
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0256
_diffrn_reflns_av_unetI/netI     0.0354
_diffrn_reflns_Laue_measured_fraction_full 0.981
_diffrn_reflns_Laue_measured_fraction_max 0.846
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            10008
_diffrn_reflns_point_group_measured_fraction_full 0.981
_diffrn_reflns_point_group_measured_fraction_max 0.846
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         28.457
_diffrn_reflns_theta_min         3.030
_diffrn_ambient_temperature      150.0
_diffrn_detector_area_resol_mean 10.3968
_diffrn_measured_fraction_theta_full 0.981
_diffrn_measured_fraction_theta_max 0.846
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -78.00   99.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -        9.9038    0.0000 -180.0000 177

#__ type_ start__ end____ width___ exp.time_
  2 omega    0.00   26.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -        9.9038  -77.0000  150.0000 26
;
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini ultra'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0230636000
_diffrn_orient_matrix_UB_12      0.0132399000
_diffrn_orient_matrix_UB_13      0.0656351000
_diffrn_orient_matrix_UB_21      0.0435063000
_diffrn_orient_matrix_UB_22      0.0262811000
_diffrn_orient_matrix_UB_23      -0.0126295000
_diffrn_orient_matrix_UB_31      -0.0549562000
_diffrn_orient_matrix_UB_32      0.0263706000
_diffrn_orient_matrix_UB_33      -0.0203218000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_special_details          ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3392
_reflns_number_total             4083
_reflns_odcompleteness_completeness 99.74
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     24.97
_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 1.171.34.49 (release 20-01-2011 CrysAlis171 .NET)
(compiled Jan 20 2011,15:58:25)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.34.49 (release 20-01-2011 CrysAlis171 .NET)
(compiled Jan 20 2011,15:58:25)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.34.49 (release 20-01-2011 CrysAlis171 .NET)
(compiled Jan 20 2011,15:58:25)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XS (Sheldrick, 2008)'
_refine_diff_density_max         0.336
_refine_diff_density_min         -0.455
_refine_diff_density_rms         0.054
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     264
_refine_ls_number_reflns         4083
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0525
_refine_ls_R_factor_gt           0.0409
_refine_ls_restrained_S_all      1.040
_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)+(0.0414P)²+1.1874P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0943
_refine_ls_wR_factor_ref         0.1019
_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:
 C10(H10), C14(H14), C15(H15)
2.b Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B)
2.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C8(H8), C17(H17), C18(H18), C20(H20), C21(H21)
2.d Idealised Me refined as rotating group:
 C12(H12A,H12B,H12C), C22(H22A,H22B,H22C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_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 0.58264(4) 0.25283(2) 0.06923(4) 0.01726(12) Uani 1 1 d . . . . .
O1 O 0.61537(15) 0.08739(8) -0.50291(13) 0.0337(3) Uani 1 1 d . . . . .
O2 O 0.84630(13) 0.19881(8) -0.10760(13) 0.0304(3) Uani 1 1 d . . . . .
O3 O 0.69321(13) 0.27104(7) 0.19269(12) 0.0235(3) Uani 1 1 d . . . . .
O4 O 0.53043(13) 0.30827(7) -0.03157(12) 0.0233(3) Uani 1 1 d . . . . .
N1 N 0.63817(14) 0.18433(8) 0.00480(13) 0.0180(3) Uani 1 1 d . . . . .
N2 N 0.75582(15) 0.13472(8) -0.30202(15) 0.0218(3) Uani 1 1 d . . . . .
C1 C 0.69513(17) 0.11752(10) 0.07837(16) 0.0183(4) Uani 1 1 d . . . . .
C2 C 0.78938(18) 0.11176(11) 0.20858(17) 0.0238(4) Uani 1 1 d . . . . .
H2 H 0.8236 0.1548 0.2619 0.029 Uiso 1 1 calc R . . . .
C3 C 0.83192(19) 0.04072(11) 0.25817(18) 0.0274(4) Uani 1 1 d . . . . .
H3 H 0.8949 0.0351 0.3477 0.033 Uiso 1 1 calc R . . . .
C4 C 0.78469(19) -0.02209(11) 0.18018(19) 0.0258(4) Uani 1 1 d . . . . .
H4 H 0.8154 -0.0700 0.2167 0.031 Uiso 1 1 calc R . . . .
C5 C 0.69296(18) -0.01557(10) 0.04927(18) 0.0226(4) Uani 1 1 d . . . . .
H5 H 0.6615 -0.0586 -0.0046 0.027 Uiso 1 1 calc R . . . .
C6 C 0.64790(17) 0.05493(10) -0.00178(17) 0.0191(4) Uani 1 1 d . . . . .
C7 C 0.55734(17) 0.07876(10) -0.13404(16) 0.0181(4) Uani 1 1 d . . . . .
C8 C 0.49272(18) 0.04390(10) -0.24898(17) 0.0209(4) Uani 1 1 d . . . . .
H8 H 0.4939 -0.0089 -0.2555 0.025 Uiso 1 1 calc R . . . .
C9 C 0.41814(18) 0.09180(10) -0.36758(17) 0.0240(4) Uani 1 1 d . . . . .
H9A H 0.3331 0.1129 -0.3632 0.029 Uiso 1 1 calc R . . . .
H9B H 0.3901 0.0613 -0.4486 0.029 Uiso 1 1 calc R . . . .
C10 C 0.51523(18) 0.15572(10) -0.37193(16) 0.0212(4) Uani 1 1 d . . . . .
H10 H 0.4614 0.1931 -0.4404 0.025 Uiso 1 1 calc R . . . .
C11 C 0.62899(19) 0.12208(10) -0.40501(17) 0.0229(4) Uani 1 1 d . . . . .
C12 C 0.8861(2) 0.10507(12) -0.2986(2) 0.0318(5) Uani 1 1 d . . . . .
H12A H 0.9625 0.1386 -0.2476 0.048 Uiso 1 1 calc GR . . . .
H12B H 0.8804 0.1009 -0.3887 0.048 Uiso 1 1 calc GR . . . .
H12C H 0.9030 0.0557 -0.2573 0.048 Uiso 1 1 calc GR . . . .
C13 C 0.74668(18) 0.17860(10) -0.20371(17) 0.0207(4) Uani 1 1 d . . . . .
C14 C 0.59421(17) 0.19504(10) -0.23774(16) 0.0186(4) Uani 1 1 d . . . . .
H14 H 0.5769 0.2500 -0.2468 0.022 Uiso 1 1 calc R . . . .
C15 C 0.54799(17) 0.16267(10) -0.13287(15) 0.0175(3) Uani 1 1 d . . . . .
H15 H 0.4498 0.1779 -0.1536 0.021 Uiso 1 1 calc R . . . .
C16 C 0.44273(17) 0.21687(9) 0.10028(16) 0.0173(3) Uani 1 1 d . . . . .
C17 C 0.30756(18) 0.22595(10) 0.00666(16) 0.0195(4) Uani 1 1 d . . . . .
H17 H 0.2900 0.2545 -0.0706 0.023 Uiso 1 1 calc R . . . .
C18 C 0.19850(18) 0.19302(10) 0.02693(18) 0.0232(4) Uani 1 1 d . . . . .
H18 H 0.1059 0.1996 -0.0365 0.028 Uiso 1 1 calc R . . . .
C19 C 0.22282(19) 0.15035(10) 0.13913(18) 0.0231(4) Uani 1 1 d . . . . .
C20 C 0.35860(19) 0.14412(10) 0.23332(17) 0.0223(4) Uani 1 1 d . . . . .
H20 H 0.3760 0.1170 0.3119 0.027 Uiso 1 1 calc R . . . .
C21 C 0.46887(18) 0.17655(10) 0.21500(16) 0.0200(4) Uani 1 1 d . . . . .
H21 H 0.5611 0.1714 0.2798 0.024 Uiso 1 1 calc R . . . .
C22 C 0.1054(2) 0.10994(12) 0.1561(2) 0.0355(5) Uani 1 1 d . . . . .
H22A H 0.0172 0.1349 0.1041 0.053 Uiso 1 1 calc GR . . . .
H22B H 0.1210 0.1103 0.2494 0.053 Uiso 1 1 calc GR . . . .
H22C H 0.1016 0.0583 0.1259 0.053 Uiso 1 1 calc GR . . . .


_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 O3 1.4306(12) . ?
S1 O4 1.4302(12) . ?
S1 N1 1.6435(14) . ?
S1 C16 1.7633(17) . ?
O1 C11 1.209(2) . ?
O2 C13 1.209(2) . ?
N1 C1 1.438(2) . ?
N1 C15 1.487(2) . ?
N2 C11 1.379(2) . ?
N2 C12 1.455(2) . ?
N2 C13 1.380(2) . ?
C1 C2 1.386(2) . ?
C1 C6 1.394(2) . ?
C2 H2 0.9500 . ?
C2 C3 1.389(3) . ?
C3 H3 0.9500 . ?
C3 C4 1.385(3) . ?
C4 H4 0.9500 . ?
C4 C5 1.386(3) . ?
C5 H5 0.9500 . ?
C5 C6 1.389(2) . ?
C6 C7 1.454(2) . ?
C7 C8 1.334(2) . ?
C7 C15 1.510(2) . ?
C8 H8 0.9500 . ?
C8 C9 1.500(2) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C9 C10 1.549(3) . ?
C10 H10 1.0000 . ?
C10 C11 1.512(2) . ?
C10 C14 1.551(2) . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 C14 1.520(2) . ?
C14 H14 1.0000 . ?
C14 C15 1.545(2) . ?
C15 H15 1.0000 . ?
C16 C17 1.390(2) . ?
C16 C21 1.392(2) . ?
C17 H17 0.9500 . ?
C17 C18 1.387(3) . ?
C18 H18 0.9500 . ?
C18 C19 1.394(3) . ?
C19 C20 1.391(2) . ?
C19 C22 1.508(3) . ?
C20 H20 0.9500 . ?
C20 C21 1.384(2) . ?
C21 H21 0.9500 . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?

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
O3 S1 N1 107.06(7) . . ?
O3 S1 C16 108.39(8) . . ?
O4 S1 O3 119.75(8) . . ?
O4 S1 N1 105.75(7) . . ?
O4 S1 C16 108.71(8) . . ?
N1 S1 C16 106.41(7) . . ?
C1 N1 S1 121.09(11) . . ?
C1 N1 C15 108.15(13) . . ?
C15 N1 S1 116.83(11) . . ?
C11 N2 C12 123.05(16) . . ?
C11 N2 C13 113.31(15) . . ?
C13 N2 C12 123.64(16) . . ?
C2 C1 N1 127.73(16) . . ?
C2 C1 C6 121.67(16) . . ?
C6 C1 N1 110.53(14) . . ?
C1 C2 H2 121.3 . . ?
C1 C2 C3 117.47(17) . . ?
C3 C2 H2 121.3 . . ?
C2 C3 H3 119.2 . . ?
C4 C3 C2 121.52(17) . . ?
C4 C3 H3 119.2 . . ?
C3 C4 H4 119.7 . . ?
C3 C4 C5 120.53(17) . . ?
C5 C4 H4 119.7 . . ?
C4 C5 H5 120.6 . . ?
C4 C5 C6 118.84(17) . . ?
C6 C5 H5 120.6 . . ?
C1 C6 C7 109.03(15) . . ?
C5 C6 C1 119.95(16) . . ?
C5 C6 C7 130.99(16) . . ?
C6 C7 C15 107.65(14) . . ?
C8 C7 C6 134.42(17) . . ?
C8 C7 C15 117.80(15) . . ?
C7 C8 H8 121.5 . . ?
C7 C8 C9 116.97(16) . . ?
C9 C8 H8 121.5 . . ?
C8 C9 H9A 109.8 . . ?
C8 C9 H9B 109.8 . . ?
C8 C9 C10 109.54(14) . . ?
H9A C9 H9B 108.2 . . ?
C10 C9 H9A 109.8 . . ?
C10 C9 H9B 109.8 . . ?
C9 C10 H10 110.1 . . ?
C9 C10 C14 114.24(14) . . ?
C11 C10 C9 107.94(15) . . ?
C11 C10 H10 110.1 . . ?
C11 C10 C14 104.25(13) . . ?
C14 C10 H10 110.1 . . ?
O1 C11 N2 123.53(17) . . ?
O1 C11 C10 127.31(17) . . ?
N2 C11 C10 109.13(15) . . ?
N2 C12 H12A 109.5 . . ?
N2 C12 H12B 109.5 . . ?
N2 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
O2 C13 N2 123.77(17) . . ?
O2 C13 C14 127.67(17) . . ?
N2 C13 C14 108.55(14) . . ?
C10 C14 H14 110.3 . . ?
C13 C14 C10 104.56(14) . . ?
C13 C14 H14 110.3 . . ?
C13 C14 C15 111.20(13) . . ?
C15 C14 C10 110.06(14) . . ?
C15 C14 H14 110.3 . . ?
N1 C15 C7 104.65(13) . . ?
N1 C15 C14 114.30(14) . . ?
N1 C15 H15 109.5 . . ?
C7 C15 C14 109.10(14) . . ?
C7 C15 H15 109.5 . . ?
C14 C15 H15 109.5 . . ?
C17 C16 S1 119.52(13) . . ?
C17 C16 C21 120.58(16) . . ?
C21 C16 S1 119.83(13) . . ?
C16 C17 H17 120.3 . . ?
C18 C17 C16 119.43(16) . . ?
C18 C17 H17 120.3 . . ?
C17 C18 H18 119.5 . . ?
C17 C18 C19 120.92(16) . . ?
C19 C18 H18 119.5 . . ?
C18 C19 C22 120.80(17) . . ?
C20 C19 C18 118.47(16) . . ?
C20 C19 C22 120.70(17) . . ?
C19 C20 H20 119.3 . . ?
C21 C20 C19 121.46(17) . . ?
C21 C20 H20 119.3 . . ?
C16 C21 H21 120.5 . . ?
C20 C21 C16 119.07(16) . . ?
C20 C21 H21 120.5 . . ?
C19 C22 H22A 109.5 . . ?
C19 C22 H22B 109.5 . . ?
C19 C22 H22C 109.5 . . ?
H22A C22 H22B 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 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
S1 N1 C1 C2 -44.4(2) . . . . ?
S1 N1 C1 C6 138.64(13) . . . . ?
S1 N1 C15 C7 -141.07(12) . . . . ?
S1 N1 C15 C14 99.65(15) . . . . ?
S1 C16 C17 C18 175.36(13) . . . . ?
S1 C16 C21 C20 -175.34(13) . . . . ?
O2 C13 C14 C10 179.43(18) . . . . ?
O2 C13 C14 C15 -61.8(2) . . . . ?
O3 S1 N1 C1 52.77(14) . . . . ?
O3 S1 N1 C15 -171.80(11) . . . . ?
O3 S1 C16 C17 151.09(13) . . . . ?
O3 S1 C16 C21 -32.09(16) . . . . ?
O4 S1 N1 C1 -178.48(12) . . . . ?
O4 S1 N1 C15 -43.05(13) . . . . ?
O4 S1 C16 C17 19.42(16) . . . . ?
O4 S1 C16 C21 -163.75(13) . . . . ?
N1 S1 C16 C17 -94.06(14) . . . . ?
N1 S1 C16 C21 82.76(15) . . . . ?
N1 C1 C2 C3 -178.78(16) . . . . ?
N1 C1 C6 C5 178.60(15) . . . . ?
N1 C1 C6 C7 0.55(19) . . . . ?
N2 C13 C14 C10 -1.12(18) . . . . ?
N2 C13 C14 C15 117.63(15) . . . . ?
C1 N1 C15 C7 -0.30(17) . . . . ?
C1 N1 C15 C14 -119.58(15) . . . . ?
C1 C2 C3 C4 1.4(3) . . . . ?
C1 C6 C7 C8 174.74(18) . . . . ?
C1 C6 C7 C15 -0.73(18) . . . . ?
C2 C1 C6 C5 1.4(2) . . . . ?
C2 C1 C6 C7 -176.61(15) . . . . ?
C2 C3 C4 C5 0.1(3) . . . . ?
C3 C4 C5 C6 -0.8(3) . . . . ?
C4 C5 C6 C1 0.1(2) . . . . ?
C4 C5 C6 C7 177.64(17) . . . . ?
C5 C6 C7 C8 -3.0(3) . . . . ?
C5 C6 C7 C15 -178.49(17) . . . . ?
C6 C1 C2 C3 -2.1(3) . . . . ?
C6 C7 C8 C9 -174.17(18) . . . . ?
C6 C7 C15 N1 0.61(17) . . . . ?
C6 C7 C15 C14 123.34(14) . . . . ?
C7 C8 C9 C10 48.5(2) . . . . ?
C8 C7 C15 N1 -175.72(14) . . . . ?
C8 C7 C15 C14 -53.0(2) . . . . ?
C8 C9 C10 C11 70.26(17) . . . . ?
C8 C9 C10 C14 -45.2(2) . . . . ?
C9 C10 C11 O1 59.9(2) . . . . ?
C9 C10 C11 N2 -118.09(15) . . . . ?
C9 C10 C14 C13 116.04(15) . . . . ?
C9 C10 C14 C15 -3.5(2) . . . . ?
C10 C14 C15 N1 167.38(13) . . . . ?
C10 C14 C15 C7 50.63(17) . . . . ?
C11 N2 C13 O2 -176.78(17) . . . . ?
C11 N2 C13 C14 3.7(2) . . . . ?
C11 C10 C14 C13 -1.53(17) . . . . ?
C11 C10 C14 C15 -121.04(15) . . . . ?
C12 N2 C11 O1 -2.4(3) . . . . ?
C12 N2 C11 C10 175.70(16) . . . . ?
C12 N2 C13 O2 2.7(3) . . . . ?
C12 N2 C13 C14 -176.78(15) . . . . ?
C13 N2 C11 O1 177.12(17) . . . . ?
C13 N2 C11 C10 -4.8(2) . . . . ?
C13 C14 C15 N1 51.98(19) . . . . ?
C13 C14 C15 C7 -64.76(17) . . . . ?
C14 C10 C11 O1 -178.29(18) . . . . ?
C14 C10 C11 N2 3.73(18) . . . . ?
C15 N1 C1 C2 176.80(16) . . . . ?
C15 N1 C1 C6 -0.14(18) . . . . ?
C15 C7 C8 C9 0.9(2) . . . . ?
C16 S1 N1 C1 -62.98(14) . . . . ?
C16 S1 N1 C15 72.46(13) . . . . ?
C16 C17 C18 C19 -0.7(3) . . . . ?
C17 C16 C21 C20 1.5(2) . . . . ?
C17 C18 C19 C20 2.7(3) . . . . ?
C17 C18 C19 C22 -175.44(17) . . . . ?
C18 C19 C20 C21 -2.7(3) . . . . ?
C19 C20 C21 C16 0.7(3) . . . . ?
C21 C16 C17 C18 -1.4(2) . . . . ?
C22 C19 C20 C21 175.45(17) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_mjh120042
_database_code_depnum_ccdc_archive 'CCDC 952357'
_audit_update_record             
;
2014-12-18 deposited with the CCDC.
2015-01-16 downloaded from the CCDC.
;
_audit_creation_date             2014-12-02
_audit_creation_method           
;
Olex2 1.2-alpha
(compiled 2014.11.21 svn.r3095 for OlexSys, GUI svn.r4949)
;
_shelxl_version_number           2014/6
_chemical_name_common            ?
_chemical_name_systematic        
(3aS*,5S*,10bS*)-5-((S*)-hydroxy(perfluorophenyl)methyl)-N,N-dimethyl-1,3-dioxo-1,3,3a,4,5,10b-hexahydropyrrolo[3,4-a]carbazole-10(2H)-sulfonamide
_chemical_formula_moiety         'C24 H20 F5 N3 O5 S'
_chemical_formula_sum            'C24 H20 F5 N3 O5 S'
_chemical_formula_weight         557.49
_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 0.0033 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'
F F 0.0171 0.0103 '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'

_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                   7.9070(4)
_cell_length_b                   14.2862(7)
_cell_length_c                   20.6839(10)
_cell_angle_alpha                90
_cell_angle_beta                 101.016(5)
_cell_angle_gamma                90
_cell_volume                     2293.4(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    5543
_cell_measurement_temperature    150.0
_cell_measurement_theta_max      28.5224
_cell_measurement_theta_min      2.8459
_shelx_estimated_absorpt_T_max   0.978
_shelx_estimated_absorpt_T_min   0.967
_exptl_absorpt_coefficient_mu    0.227
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.98002
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET)
(compiled Jan 23 2012,18:06:46)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.615
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1144
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0596
_diffrn_reflns_av_unetI/netI     0.0600
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.876
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            23890
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.876
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         28.585
_diffrn_reflns_theta_min         2.852
_diffrn_ambient_temperature      150.00
_diffrn_detector_area_resol_mean 10.3968
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.876
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -91.00  -64.75   0.7500   70.0000
omega____ theta____ kappa____ phi______ frames
    -       -8.1850 -167.0000   26.0000 35

#__ type_ start__ end____ width___ exp.time_
  2 omega  -87.00   15.00   0.7500   70.0000
omega____ theta____ kappa____ phi______ frames
    -       -8.1850  -77.0000  120.0000 136

#__ type_ start__ end____ width___ exp.time_
  3 omega  -11.00   77.50   0.7500   70.0000
omega____ theta____ kappa____ phi______ frames
    -        9.9038   38.0000   60.0000 118

#__ type_ start__ end____ width___ exp.time_
  4 omega    5.00   49.25   0.7500   70.0000
omega____ theta____ kappa____ phi______ frames
    -        9.9038  -99.0000 -180.0000 59

#__ type_ start__ end____ width___ exp.time_
  5 omega  -39.00   -6.00   0.7500   70.0000
omega____ theta____ kappa____ phi______ frames
    -        9.9038  115.0000  -98.0000 44

#__ type_ start__ end____ width___ exp.time_
  6 omega  -61.00  -35.50   0.7500   70.0000
omega____ theta____ kappa____ phi______ frames
    -        9.9038  -38.0000  -90.0000 34

#__ type_ start__ end____ width___ exp.time_
  7 omega  -63.00   25.50   0.7500   70.0000
omega____ theta____ kappa____ phi______ frames
    -        9.9038  -57.0000    0.0000 118
;
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini ultra'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0645809000
_diffrn_orient_matrix_UB_12      -0.0234370000
_diffrn_orient_matrix_UB_13      0.0133676000
_diffrn_orient_matrix_UB_21      -0.0645493000
_diffrn_orient_matrix_UB_22      0.0212721000
_diffrn_orient_matrix_UB_23      -0.0240350000
_diffrn_orient_matrix_UB_31      0.0036687000
_diffrn_orient_matrix_UB_32      -0.0382610000
_diffrn_orient_matrix_UB_33      -0.0215446000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3582
_reflns_number_total             5125
_reflns_odcompleteness_completeness 98.94
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     24.97
_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 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET)
(compiled Jan 23 2012,18:06:46)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET)
(compiled Jan 23 2012,18:06:46)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET)
(compiled Jan 23 2012,18:06:46)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.344
_refine_diff_density_min         -0.374
_refine_diff_density_rms         0.067
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     350
_refine_ls_number_reflns         5125
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0864
_refine_ls_R_factor_gt           0.0492
_refine_ls_restrained_S_all      1.027
_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)+(0.0402P)²+1.5042P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0954
_refine_ls_wR_factor_ref         0.1108
_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:
 C8(H8), C10(H10), C14(H14), C16(H16)
2.b Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B)
2.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5)
2.d Idealised Me refined as rotating group:
 C12(H12A,H12B,H12C), C23(H23A,H23B,H23C), C24(H24A,H24B,H24C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_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 0.46959(7) 0.65635(4) 0.17030(3) 0.01928(15) Uani 1 1 d . . . . .
N1 N 0.3931(2) 0.55706(13) 0.19691(9) 0.0181(4) Uani 1 1 d . . . . .
N2 N 0.7675(2) 0.52493(14) 0.38422(9) 0.0226(4) Uani 1 1 d . . . . .
N3 N 0.3995(3) 0.65172(14) 0.09267(10) 0.0241(5) Uani 1 1 d . . . . .
O1 O 0.6788(2) 0.29096(12) 0.18756(8) 0.0230(4) Uani 1 1 d . . . . .
H1 H 0.750(4) 0.249(2) 0.1891(16) 0.048(10) Uiso 1 1 d . . . . .
O2 O 0.8964(2) 0.38689(13) 0.42162(9) 0.0360(5) Uani 1 1 d . . . . .
O3 O 0.5996(2) 0.63771(11) 0.32514(8) 0.0255(4) Uani 1 1 d . . . . .
O4 O 0.3911(2) 0.73447(12) 0.19474(9) 0.0308(4) Uani 1 1 d . . . . .
O5 O 0.65194(19) 0.64614(11) 0.18610(8) 0.0244(4) Uani 1 1 d . . . . .
F1 F 0.43401(19) 0.34931(9) 0.08380(7) 0.0296(3) Uani 1 1 d . . . . .
F2 F 0.2037(2) 0.28723(11) -0.01786(7) 0.0413(4) Uani 1 1 d . . . . .
F3 F 0.0529(2) 0.11765(12) -0.01300(7) 0.0442(4) Uani 1 1 d . . . . .
F4 F 0.1362(2) 0.01007(11) 0.09704(8) 0.0433(4) Uani 1 1 d . . . . .
F5 F 0.3670(2) 0.07104(10) 0.20033(7) 0.0343(4) Uani 1 1 d . . . . .
C1 C 0.2278(3) 0.52246(16) 0.16985(11) 0.0189(5) Uani 1 1 d . . . . .
C2 C 0.0848(3) 0.56980(18) 0.13576(12) 0.0256(6) Uani 1 1 d . . . . .
H2 H 0.0886 0.6349 0.1269 0.031 Uiso 1 1 calc R . . . .
C3 C -0.0634(3) 0.5180(2) 0.11537(13) 0.0314(6) Uani 1 1 d . . . . .
H3 H -0.1634 0.5480 0.0916 0.038 Uiso 1 1 calc R . . . .
C4 C -0.0690(3) 0.4226(2) 0.12892(13) 0.0318(6) Uani 1 1 d . . . . .
H4 H -0.1724 0.3887 0.1138 0.038 Uiso 1 1 calc R . . . .
C5 C 0.0732(3) 0.37630(18) 0.16407(12) 0.0253(6) Uani 1 1 d . . . . .
H5 H 0.0676 0.3116 0.1741 0.030 Uiso 1 1 calc R . . . .
C6 C 0.2246(3) 0.42696(17) 0.18431(11) 0.0184(5) Uani 1 1 d . . . . .
C7 C 0.3928(3) 0.40259(16) 0.22190(11) 0.0170(5) Uani 1 1 d . . . . .
C8 C 0.4554(3) 0.31048(16) 0.25249(11) 0.0183(5) Uani 1 1 d . . . . .
H8 H 0.3535 0.2770 0.2636 0.022 Uiso 1 1 calc R . . . .
C9 C 0.5803(3) 0.33057(16) 0.31749(11) 0.0197(5) Uani 1 1 d . . . . .
H9A H 0.6316 0.2708 0.3359 0.024 Uiso 1 1 calc R . . . .
H9B H 0.5147 0.3573 0.3494 0.024 Uiso 1 1 calc R . . . .
C10 C 0.7266(3) 0.39872(16) 0.30981(11) 0.0198(5) Uani 1 1 d . . . . .
H10 H 0.8129 0.3665 0.2879 0.024 Uiso 1 1 calc R . . . .
C11 C 0.8112(3) 0.43190(17) 0.37772(12) 0.0238(5) Uani 1 1 d . . . . .
C12 C 0.8103(3) 0.57686(19) 0.44585(12) 0.0310(6) Uani 1 1 d . . . . .
H12A H 0.9354 0.5761 0.4614 0.046 Uiso 1 1 calc GR . . . .
H12B H 0.7536 0.5477 0.4789 0.046 Uiso 1 1 calc GR . . . .
H12C H 0.7707 0.6417 0.4386 0.046 Uiso 1 1 calc GR . . . .
C13 C 0.6676(3) 0.56130(17) 0.32784(11) 0.0199(5) Uani 1 1 d . . . . .
C14 C 0.6637(3) 0.49005(16) 0.27277(11) 0.0182(5) Uani 1 1 d . . . . .
H14 H 0.7489 0.5091 0.2452 0.022 Uiso 1 1 calc R . . . .
C15 C 0.4896(3) 0.48087(16) 0.22936(11) 0.0168(5) Uani 1 1 d . . . . .
C16 C 0.5370(3) 0.24560(16) 0.20755(11) 0.0185(5) Uani 1 1 d . . . . .
H16 H 0.5819 0.1889 0.2337 0.022 Uiso 1 1 calc R . . . .
C17 C 0.4079(3) 0.21313(16) 0.14720(11) 0.0188(5) Uani 1 1 d . . . . .
C18 C 0.3632(3) 0.26494(16) 0.08976(11) 0.0209(5) Uani 1 1 d . . . . .
C19 C 0.2447(3) 0.23364(18) 0.03639(12) 0.0271(6) Uani 1 1 d . . . . .
C20 C 0.1684(3) 0.14838(18) 0.03879(12) 0.0277(6) Uani 1 1 d . . . . .
C21 C 0.2092(3) 0.09445(18) 0.09422(13) 0.0284(6) Uani 1 1 d . . . . .
C22 C 0.3278(3) 0.12723(17) 0.14718(11) 0.0229(5) Uani 1 1 d . . . . .
C23 C 0.3026(4) 0.7274(2) 0.05539(14) 0.0389(7) Uani 1 1 d . . . . .
H23A H 0.2705 0.7736 0.0859 0.058 Uiso 1 1 calc GR . . . .
H23B H 0.1982 0.7020 0.0277 0.058 Uiso 1 1 calc GR . . . .
H23C H 0.3739 0.7575 0.0275 0.058 Uiso 1 1 calc GR . . . .
C24 C 0.4464(3) 0.57242(18) 0.05618(13) 0.0298(6) Uani 1 1 d . . . . .
H24A H 0.5190 0.5937 0.0256 0.045 Uiso 1 1 calc GR . . . .
H24B H 0.3419 0.5431 0.0313 0.045 Uiso 1 1 calc GR . . . .
H24C H 0.5101 0.5268 0.0869 0.045 Uiso 1 1 calc GR . . . .


_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 N1 1.6756(19) . ?
S1 N3 1.597(2) . ?
S1 O4 1.4165(17) . ?
S1 O5 1.4237(16) . ?
N1 C1 1.410(3) . ?
N1 C15 1.422(3) . ?
N2 C11 1.386(3) . ?
N2 C12 1.458(3) . ?
N2 C13 1.379(3) . ?
N3 C23 1.458(3) . ?
N3 C24 1.448(3) . ?
O1 H1 0.82(3) . ?
O1 C16 1.423(3) . ?
O2 C11 1.207(3) . ?
O3 C13 1.213(3) . ?
F1 C18 1.345(3) . ?
F2 C19 1.346(3) . ?
F3 C20 1.342(3) . ?
F4 C21 1.342(3) . ?
F5 C22 1.349(3) . ?
C1 C2 1.389(3) . ?
C1 C6 1.398(3) . ?
C2 H2 0.9500 . ?
C2 C3 1.382(3) . ?
C3 H3 0.9500 . ?
C3 C4 1.394(4) . ?
C4 H4 0.9500 . ?
C4 C5 1.385(3) . ?
C5 H5 0.9500 . ?
C5 C6 1.393(3) . ?
C6 C7 1.449(3) . ?
C7 C8 1.502(3) . ?
C7 C15 1.347(3) . ?
C8 H8 1.0000 . ?
C8 C9 1.536(3) . ?
C8 C16 1.539(3) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C9 C10 1.543(3) . ?
C10 H10 1.0000 . ?
C10 C11 1.512(3) . ?
C10 C14 1.546(3) . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 C14 1.524(3) . ?
C14 H14 1.0000 . ?
C14 C15 1.498(3) . ?
C16 H16 1.0000 . ?
C16 C17 1.526(3) . ?
C17 C18 1.387(3) . ?
C17 C22 1.381(3) . ?
C18 C19 1.379(3) . ?
C19 C20 1.365(4) . ?
C20 C21 1.368(4) . ?
C21 C22 1.381(3) . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 0.9800 . ?
C24 H24A 0.9800 . ?
C24 H24B 0.9800 . ?
C24 H24C 0.9800 . ?

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
N3 S1 N1 102.57(10) . . ?
O4 S1 N1 109.84(10) . . ?
O4 S1 N3 107.46(11) . . ?
O4 S1 O5 119.51(10) . . ?
O5 S1 N1 104.54(9) . . ?
O5 S1 N3 111.60(10) . . ?
C1 N1 S1 122.14(15) . . ?
C1 N1 C15 107.00(18) . . ?
C15 N1 S1 127.46(15) . . ?
C11 N2 C12 123.5(2) . . ?
C13 N2 C11 113.11(19) . . ?
C13 N2 C12 123.2(2) . . ?
C23 N3 S1 123.20(18) . . ?
C24 N3 S1 118.83(16) . . ?
C24 N3 C23 117.7(2) . . ?
C16 O1 H1 103(2) . . ?
C2 C1 N1 129.4(2) . . ?
C2 C1 C6 122.5(2) . . ?
C6 C1 N1 108.07(19) . . ?
C1 C2 H2 121.5 . . ?
C3 C2 C1 117.0(2) . . ?
C3 C2 H2 121.5 . . ?
C2 C3 H3 119.3 . . ?
C2 C3 C4 121.4(2) . . ?
C4 C3 H3 119.3 . . ?
C3 C4 H4 119.4 . . ?
C5 C4 C3 121.2(2) . . ?
C5 C4 H4 119.4 . . ?
C4 C5 H5 120.8 . . ?
C4 C5 C6 118.3(2) . . ?
C6 C5 H5 120.8 . . ?
C1 C6 C7 107.30(19) . . ?
C5 C6 C1 119.5(2) . . ?
C5 C6 C7 133.2(2) . . ?
C6 C7 C8 129.1(2) . . ?
C15 C7 C6 107.8(2) . . ?
C15 C7 C8 123.0(2) . . ?
C7 C8 H8 107.5 . . ?
C7 C8 C9 108.06(18) . . ?
C7 C8 C16 114.55(18) . . ?
C9 C8 H8 107.5 . . ?
C9 C8 C16 111.56(18) . . ?
C16 C8 H8 107.5 . . ?
C8 C9 H9A 108.9 . . ?
C8 C9 H9B 108.9 . . ?
C8 C9 C10 113.41(18) . . ?
H9A C9 H9B 107.7 . . ?
C10 C9 H9A 108.9 . . ?
C10 C9 H9B 108.9 . . ?
C9 C10 H10 110.3 . . ?
C9 C10 C14 114.00(18) . . ?
C11 C10 C9 108.02(19) . . ?
C11 C10 H10 110.3 . . ?
C11 C10 C14 103.83(18) . . ?
C14 C10 H10 110.3 . . ?
N2 C11 C10 108.45(19) . . ?
O2 C11 N2 123.4(2) . . ?
O2 C11 C10 128.0(2) . . ?
N2 C12 H12A 109.5 . . ?
N2 C12 H12B 109.5 . . ?
N2 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
N2 C13 C14 107.87(19) . . ?
O3 C13 N2 123.7(2) . . ?
O3 C13 C14 128.4(2) . . ?
C10 C14 H14 108.9 . . ?
C13 C14 C10 103.57(18) . . ?
C13 C14 H14 108.9 . . ?
C15 C14 C10 113.25(19) . . ?
C15 C14 C13 113.05(18) . . ?
C15 C14 H14 108.9 . . ?
N1 C15 C14 124.4(2) . . ?
C7 C15 N1 109.83(19) . . ?
C7 C15 C14 125.3(2) . . ?
O1 C16 C8 110.23(18) . . ?
O1 C16 H16 107.9 . . ?
O1 C16 C17 109.99(18) . . ?
C8 C16 H16 107.9 . . ?
C17 C16 C8 112.63(18) . . ?
C17 C16 H16 107.9 . . ?
C18 C17 C16 124.0(2) . . ?
C22 C17 C16 120.4(2) . . ?
C22 C17 C18 115.6(2) . . ?
F1 C18 C17 121.0(2) . . ?
F1 C18 C19 116.6(2) . . ?
C19 C18 C17 122.4(2) . . ?
F2 C19 C18 120.1(2) . . ?
F2 C19 C20 120.0(2) . . ?
C20 C19 C18 119.9(2) . . ?
F3 C20 C19 120.1(2) . . ?
F3 C20 C21 120.0(2) . . ?
C19 C20 C21 119.9(2) . . ?
F4 C21 C20 120.5(2) . . ?
F4 C21 C22 120.2(2) . . ?
C20 C21 C22 119.3(2) . . ?
F5 C22 C17 119.6(2) . . ?
F5 C22 C21 117.4(2) . . ?
C21 C22 C17 122.9(2) . . ?
N3 C23 H23A 109.5 . . ?
N3 C23 H23B 109.5 . . ?
N3 C23 H23C 109.5 . . ?
H23A C23 H23B 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
N3 C24 H24A 109.5 . . ?
N3 C24 H24B 109.5 . . ?
N3 C24 H24C 109.5 . . ?
H24A C24 H24B 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O1 H1 O3 0.82(3) 2.04(3) 2.847(2) 169(3) 2_645

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 N1 C1 C2 -22.1(3) . . . . ?
S1 N1 C1 C6 159.42(16) . . . . ?
S1 N1 C15 C7 -157.82(17) . . . . ?
S1 N1 C15 C14 29.8(3) . . . . ?
N1 S1 N3 C23 127.4(2) . . . . ?
N1 S1 N3 C24 -58.12(19) . . . . ?
N1 C1 C2 C3 -179.1(2) . . . . ?
N1 C1 C6 C5 178.6(2) . . . . ?
N1 C1 C6 C7 0.5(2) . . . . ?
N2 C13 C14 C10 16.5(2) . . . . ?
N2 C13 C14 C15 139.49(19) . . . . ?
N3 S1 N1 C1 -38.51(19) . . . . ?
N3 S1 N1 C15 117.89(19) . . . . ?
O1 C16 C17 C18 -39.9(3) . . . . ?
O1 C16 C17 C22 139.7(2) . . . . ?
O3 C13 C14 C10 -164.5(2) . . . . ?
O3 C13 C14 C15 -41.5(3) . . . . ?
O4 S1 N1 C1 75.52(19) . . . . ?
O4 S1 N1 C15 -128.08(19) . . . . ?
O4 S1 N3 C23 11.6(2) . . . . ?
O4 S1 N3 C24 -173.89(18) . . . . ?
O5 S1 N1 C1 -155.09(17) . . . . ?
O5 S1 N1 C15 1.3(2) . . . . ?
O5 S1 N3 C23 -121.2(2) . . . . ?
O5 S1 N3 C24 53.3(2) . . . . ?
F1 C18 C19 F2 -0.8(3) . . . . ?
F1 C18 C19 C20 179.6(2) . . . . ?
F2 C19 C20 F3 0.3(4) . . . . ?
F2 C19 C20 C21 -179.4(2) . . . . ?
F3 C20 C21 F4 0.9(4) . . . . ?
F3 C20 C21 C22 -179.8(2) . . . . ?
F4 C21 C22 F5 0.7(3) . . . . ?
F4 C21 C22 C17 179.7(2) . . . . ?
C1 N1 C15 C7 1.4(2) . . . . ?
C1 N1 C15 C14 -170.9(2) . . . . ?
C1 C2 C3 C4 0.5(4) . . . . ?
C1 C6 C7 C8 176.7(2) . . . . ?
C1 C6 C7 C15 0.3(2) . . . . ?
C2 C1 C6 C5 0.0(3) . . . . ?
C2 C1 C6 C7 -178.1(2) . . . . ?
C2 C3 C4 C5 0.8(4) . . . . ?
C3 C4 C5 C6 -1.6(4) . . . . ?
C4 C5 C6 C1 1.2(3) . . . . ?
C4 C5 C6 C7 178.7(2) . . . . ?
C5 C6 C7 C8 -1.0(4) . . . . ?
C5 C6 C7 C15 -177.3(2) . . . . ?
C6 C1 C2 C3 -0.9(3) . . . . ?
C6 C7 C8 C9 -144.5(2) . . . . ?
C6 C7 C8 C16 90.5(3) . . . . ?
C6 C7 C15 N1 -1.1(2) . . . . ?
C6 C7 C15 C14 171.2(2) . . . . ?
C7 C8 C9 C10 -52.9(2) . . . . ?
C7 C8 C16 O1 58.1(2) . . . . ?
C7 C8 C16 C17 -65.1(2) . . . . ?
C8 C7 C15 N1 -177.73(19) . . . . ?
C8 C7 C15 C14 -5.5(3) . . . . ?
C8 C9 C10 C11 165.64(19) . . . . ?
C8 C9 C10 C14 50.8(3) . . . . ?
C8 C16 C17 C18 83.5(3) . . . . ?
C8 C16 C17 C22 -96.9(2) . . . . ?
C9 C8 C16 O1 -65.0(2) . . . . ?
C9 C8 C16 C17 171.72(18) . . . . ?
C9 C10 C11 N2 -108.8(2) . . . . ?
C9 C10 C11 O2 67.8(3) . . . . ?
C9 C10 C14 C13 100.2(2) . . . . ?
C9 C10 C14 C15 -22.6(3) . . . . ?
C10 C14 C15 N1 171.35(19) . . . . ?
C10 C14 C15 C7 0.2(3) . . . . ?
C11 N2 C13 O3 171.6(2) . . . . ?
C11 N2 C13 C14 -9.4(3) . . . . ?
C11 C10 C14 C13 -17.1(2) . . . . ?
C11 C10 C14 C15 -139.90(19) . . . . ?
C12 N2 C11 O2 -4.0(4) . . . . ?
C12 N2 C11 C10 172.9(2) . . . . ?
C12 N2 C13 O3 -3.6(4) . . . . ?
C12 N2 C13 C14 175.5(2) . . . . ?
C13 N2 C11 O2 -179.1(2) . . . . ?
C13 N2 C11 C10 -2.3(3) . . . . ?
C13 C14 C15 N1 53.9(3) . . . . ?
C13 C14 C15 C7 -117.2(2) . . . . ?
C14 C10 C11 N2 12.5(2) . . . . ?
C14 C10 C11 O2 -170.8(2) . . . . ?
C15 N1 C1 C2 177.3(2) . . . . ?
C15 N1 C1 C6 -1.2(2) . . . . ?
C15 C7 C8 C9 31.4(3) . . . . ?
C15 C7 C8 C16 -93.6(3) . . . . ?
C16 C8 C9 C10 73.9(2) . . . . ?
C16 C17 C18 F1 0.3(3) . . . . ?
C16 C17 C18 C19 -179.4(2) . . . . ?
C16 C17 C22 F5 -1.4(3) . . . . ?
C16 C17 C22 C21 179.6(2) . . . . ?
C17 C18 C19 F2 178.9(2) . . . . ?
C17 C18 C19 C20 -0.7(4) . . . . ?
C18 C17 C22 F5 178.2(2) . . . . ?
C18 C17 C22 C21 -0.7(3) . . . . ?
C18 C19 C20 F3 179.9(2) . . . . ?
C18 C19 C20 C21 0.2(4) . . . . ?
C19 C20 C21 F4 -179.4(2) . . . . ?
C19 C20 C21 C22 -0.1(4) . . . . ?
C20 C21 C22 F5 -178.7(2) . . . . ?
C20 C21 C22 C17 0.3(4) . . . . ?
C22 C17 C18 F1 -179.4(2) . . . . ?
C22 C17 C18 C19 0.9(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_mjh105
_database_code_depnum_ccdc_archive 'CCDC 1040305'
_audit_update_record             
;
2014-12-18 deposited with the CCDC.
2015-01-16 downloaded from the CCDC.
;
_audit_creation_date             2014-12-17
_audit_creation_method           
;
Olex2 1.2-alpha
(compiled 2014.12.09 svn.r3114 for OlexSys, GUI svn.r4963)
;
_shelxl_version_number           2014/6
_chemical_name_common            ?
_chemical_name_systematic        
2-phenyl-11-tosyl-11,11a-dihydro-1H,5H-[1,2,4]triazolo[1',2':1,2]pyridazino[3,4-b]indole-1,3(2H)-dione
_chemical_formula_moiety         'C25 H20 N4 O4 S, 0.5(C H2 Cl2)'
_chemical_formula_sum            'C25.50 H21 Cl N4 O4 S'
_chemical_formula_weight         514.97
_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'
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'
N N 0.0311 0.0180 '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'

_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                   6.2586(2)
_cell_length_b                   43.8481(9)
_cell_length_c                   17.0987(3)
_cell_angle_alpha                90
_cell_angle_beta                 93.143(2)
_cell_angle_gamma                90
_cell_volume                     4685.3(2)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    5338
_cell_measurement_temperature    150.0
_cell_measurement_theta_max      62.2533
_cell_measurement_theta_min      2.0134
_shelx_estimated_absorpt_T_max   0.779
_shelx_estimated_absorpt_T_min   0.505
_exptl_absorpt_coefficient_mu    2.634
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.90855
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.34.49 (release 20-01-2011 CrysAlis171 .NET)
(compiled Jan 20 2011,15:58:25)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.460
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             2136
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0228
_diffrn_reflns_av_unetI/netI     0.0341
_diffrn_reflns_Laue_measured_fraction_full 0.846
_diffrn_reflns_Laue_measured_fraction_max 0.968
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -3
_diffrn_reflns_limit_k_max       49
_diffrn_reflns_limit_k_min       -41
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            13831
_diffrn_reflns_point_group_measured_fraction_full 0.846
_diffrn_reflns_point_group_measured_fraction_max 0.968
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         62.340
_diffrn_reflns_theta_min         2.015
_diffrn_ambient_temperature      150.0
_diffrn_detector_area_resol_mean 10.3968
_diffrn_measured_fraction_theta_full 0.846
_diffrn_measured_fraction_theta_max 0.968
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega   42.00   90.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -       -0.0649  179.0000   90.0000 48

#__ type_ start__ end____ width___ exp.time_
  2 omega   36.00   69.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -       -0.0649  179.0000  -90.0000 33

#__ type_ start__ end____ width___ exp.time_
  3 omega  -21.00   51.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -        1.9399   38.0000 -180.0000 72

#__ type_ start__ end____ width___ exp.time_
  4 omega   63.00  144.00   1.0000   50.0000
omega____ theta____ kappa____ phi______ frames
    -       84.6210   45.0000 -150.0000 81

#__ type_ start__ end____ width___ exp.time_
  5 omega   18.00   50.00   1.0000   50.0000
omega____ theta____ kappa____ phi______ frames
    -       84.6210  -45.0000   30.0000 32

#__ type_ start__ end____ width___ exp.time_
  6 omega   29.00   77.00   1.0000   50.0000
omega____ theta____ kappa____ phi______ frames
    -       84.6210  -45.0000  -30.0000 48

#__ type_ start__ end____ width___ exp.time_
  7 omega  107.00  165.00   1.0000   50.0000
omega____ theta____ kappa____ phi______ frames
    -       84.6210   15.0000 -180.0000 58

#__ type_ start__ end____ width___ exp.time_
  8 omega   37.00   77.00   1.0000   50.0000
omega____ theta____ kappa____ phi______ frames
    -       84.6210   15.0000 -180.0000 40

#__ type_ start__ end____ width___ exp.time_
  9 omega   19.00   71.00   1.0000   50.0000
omega____ theta____ kappa____ phi______ frames
    -       84.6210  -45.0000   90.0000 52

#__ type_ start__ end____ width___ exp.time_
 10 omega    8.00   71.00   1.0000   50.0000
omega____ theta____ kappa____ phi______ frames
    -       84.6210  -77.0000  -60.0000 63
;
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini ultra'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.1523134000
_diffrn_orient_matrix_UB_12      0.0262335000
_diffrn_orient_matrix_UB_13      -0.0193410000
_diffrn_orient_matrix_UB_21      0.0066997000
_diffrn_orient_matrix_UB_22      0.0103750000
_diffrn_orient_matrix_UB_23      0.0861975000
_diffrn_orient_matrix_UB_31      0.1938529000
_diffrn_orient_matrix_UB_32      -0.0208992000
_diffrn_orient_matrix_UB_33      0.0185258000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   'Enhance Ultra (Cu) X-ray Source'
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                5694
_reflns_number_total             7203
_reflns_odcompleteness_completeness 99.94
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     58.86
_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 1.171.34.49 (release 20-01-2011 CrysAlis171 .NET)
(compiled Jan 20 2011,15:58:25)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.34.49 (release 20-01-2011 CrysAlis171 .NET)
(compiled Jan 20 2011,15:58:25)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.34.49 (release 20-01-2011 CrysAlis171 .NET)
(compiled Jan 20 2011,15:58:25)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XS (Sheldrick, 2008)'
_refine_diff_density_max         0.385
_refine_diff_density_min         -0.420
_refine_diff_density_rms         0.062
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.076
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     640
_refine_ls_number_reflns         7203
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0702
_refine_ls_R_factor_gt           0.0560
_refine_ls_restrained_S_all      1.076
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0556P)²+8.8883P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1440
_refine_ls_wR_factor_ref         0.1527
_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:
 C8(H8), C35(H35)
2.b Secondary CH2 refined with riding coordinates:
 C10(H10A,H10B), C32(H32A,H32B), C51(H51A,H51B)
2.c Me refined with riding coordinates:
 C25(H25A,H25B,H25C), C50(H50A,H50B,H50C)
2.d Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C9(H9), C14(H14), C15(H15), C16(H16),
 C17(H17), C18(H18), C20(H20), C21(H21), C23(H23), C24(H24), C27(H27), C28(H28),
  C29(H29), C30(H30), C33(H33), C39(H39), C40(H40), C41(H41), C42(H42),
 C43(H43), C45(H45), C46(H46), C48(H48), C49(H49)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_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 0.63489(14) 0.57017(2) 0.72087(5) 0.0253(2) Uani 1 1 d . . . . .
O1 O 1.2931(4) 0.68807(6) 0.83045(16) 0.0350(6) Uani 1 1 d . . . . .
O2 O 0.6505(4) 0.63729(5) 0.82397(13) 0.0288(6) Uani 1 1 d . . . . .
O3 O 0.7412(4) 0.57327(6) 0.79624(14) 0.0343(6) Uani 1 1 d . . . . .
O4 O 0.4076(4) 0.56902(6) 0.71157(15) 0.0330(6) Uani 1 1 d . . . . .
N1 N 0.7115(4) 0.60048(6) 0.66968(15) 0.0237(6) Uani 1 1 d . . . . .
N4 N 0.9651(4) 0.66501(6) 0.85139(16) 0.0250(6) Uani 1 1 d . . . . .
C1 C 0.6779(6) 0.59991(7) 0.58523(19) 0.0250(8) Uani 1 1 d . . . . .
C2 C 0.4993(6) 0.59054(8) 0.5415(2) 0.0297(8) Uani 1 1 d . . . . .
H2 H 0.3771 0.5828 0.5655 0.036 Uiso 1 1 calc R . . . .
C3 C 0.5050(7) 0.59284(9) 0.4601(2) 0.0368(10) Uani 1 1 d . . . . .
H3 H 0.3844 0.5863 0.4283 0.044 Uiso 1 1 calc R . . . .
C4 C 0.6802(7) 0.60428(9) 0.4249(2) 0.0375(10) Uani 1 1 d . . . . .
H4 H 0.6788 0.6054 0.3694 0.045 Uiso 1 1 calc R . . . .
C5 C 0.8600(7) 0.61426(8) 0.4695(2) 0.0328(9) Uani 1 1 d . . . . .
H5 H 0.9805 0.6224 0.4452 0.039 Uiso 1 1 calc R . . . .
C6 C 0.8574(6) 0.61196(8) 0.5508(2) 0.0262(8) Uani 1 1 d . . . . .
C7 C 1.0073(6) 0.62317(8) 0.6122(2) 0.0252(8) Uani 1 1 d . . . . .
C9 C 1.1652(6) 0.64337(8) 0.6098(2) 0.0311(8) Uani 1 1 d . . . . .
H9 H 1.2150 0.6490 0.5604 0.037 Uiso 1 1 calc R . . . .
C10 C 1.2665(6) 0.65737(9) 0.6819(2) 0.0335(9) Uani 1 1 d . . . . .
H10A H 1.4142 0.6495 0.6905 0.040 Uiso 1 1 calc R . . . .
H10B H 1.2742 0.6798 0.6750 0.040 Uiso 1 1 calc R . . . .
N3 N 1.1437(4) 0.65034(7) 0.75049(17) 0.0273(7) Uani 1 1 d . . . . .
N2 N 0.9287(4) 0.64016(6) 0.73893(16) 0.0253(6) Uani 1 1 d . . . . .
C8 C 0.9260(5) 0.61269(8) 0.6899(2) 0.0246(8) Uani 1 1 d . . . . .
H8 H 1.0212 0.5966 0.7141 0.030 Uiso 1 1 calc R . . . .
C11 C 1.1527(6) 0.66977(8) 0.8128(2) 0.0266(8) Uani 1 1 d . . . . .
C12 C 0.8243(6) 0.64591(8) 0.80753(19) 0.0242(8) Uani 1 1 d . . . . .
C13 C 0.9152(6) 0.68261(8) 0.9188(2) 0.0278(8) Uani 1 1 d . . . . .
C14 C 1.0651(6) 0.68469(8) 0.9806(2) 0.0337(9) Uani 1 1 d . . . . .
H14 H 1.1943 0.6733 0.9806 0.040 Uiso 1 1 calc R . . . .
C15 C 1.0235(7) 0.70380(9) 1.0433(2) 0.0429(11) Uani 1 1 d . . . . .
H15 H 1.1262 0.7058 1.0859 0.052 Uiso 1 1 calc R . . . .
C16 C 0.8324(7) 0.71983(9) 1.0433(2) 0.0433(11) Uani 1 1 d . . . . .
H16 H 0.8042 0.7328 1.0861 0.052 Uiso 1 1 calc R . . . .
C17 C 0.6845(7) 0.71703(10) 0.9818(3) 0.0451(11) Uani 1 1 d . . . . .
H17 H 0.5537 0.7280 0.9821 0.054 Uiso 1 1 calc R . . . .
C18 C 0.7241(6) 0.69830(9) 0.9189(2) 0.0356(9) Uani 1 1 d . . . . .
H18 H 0.6208 0.6963 0.8764 0.043 Uiso 1 1 calc R . . . .
C19 C 0.7406(6) 0.53780(8) 0.67548(19) 0.0253(8) Uani 1 1 d . . . . .
C20 C 0.6141(6) 0.52109(8) 0.6210(2) 0.0285(8) Uani 1 1 d . . . . .
H20 H 0.4704 0.5270 0.6082 0.034 Uiso 1 1 calc R . . . .
C21 C 0.7013(6) 0.49583(8) 0.5859(2) 0.0338(9) Uani 1 1 d . . . . .
H21 H 0.6146 0.4841 0.5498 0.041 Uiso 1 1 calc R . . . .
C22 C 0.9129(6) 0.48725(9) 0.6025(2) 0.0360(9) Uani 1 1 d . . . . .
C23 C 1.0336(6) 0.50420(9) 0.6578(3) 0.0389(10) Uani 1 1 d . . . . .
H23 H 1.1774 0.4984 0.6707 0.047 Uiso 1 1 calc R . . . .
C24 C 0.9494(6) 0.52924(8) 0.6943(2) 0.0336(9) Uani 1 1 d . . . . .
H24 H 1.0344 0.5405 0.7320 0.040 Uiso 1 1 calc R . . . .
C25 C 1.0064(8) 0.46035(9) 0.5623(3) 0.0518(12) Uani 1 1 d . . . . .
H25A H 1.1560 0.4577 0.5810 0.078 Uiso 1 1 calc R . . . .
H25B H 0.9251 0.4420 0.5740 0.078 Uiso 1 1 calc R . . . .
H25C H 0.9991 0.4638 0.5056 0.078 Uiso 1 1 calc R . . . .
Cl1 Cl 1.2636(3) 0.76779(4) 0.74318(8) 0.0829(5) Uani 1 1 d . . . . .
S2 S 1.11879(14) 0.57341(2) 0.22263(5) 0.0259(2) Uani 1 1 d . . . . .
O5 O 1.7722(4) 0.69220(6) 0.32745(15) 0.0346(6) Uani 1 1 d . . . . .
O6 O 1.1325(4) 0.64066(6) 0.32403(13) 0.0295(6) Uani 1 1 d . . . . .
O7 O 0.8918(4) 0.57156(6) 0.21283(15) 0.0338(6) Uani 1 1 d . . . . .
O8 O 1.2226(4) 0.57737(6) 0.29812(14) 0.0346(6) Uani 1 1 d . . . . .
N5 N 1.1919(4) 0.60358(6) 0.16989(15) 0.0242(6) Uani 1 1 d . . . . .
N8 N 1.4482(4) 0.66811(6) 0.35094(15) 0.0233(6) Uani 1 1 d . . . . .
C26 C 1.1638(6) 0.60133(8) 0.08550(19) 0.0250(8) Uani 1 1 d . . . . .
C27 C 0.9872(6) 0.59118(8) 0.0417(2) 0.0308(8) Uani 1 1 d . . . . .
H27 H 0.8625 0.5844 0.0658 0.037 Uiso 1 1 calc R . . . .
C28 C 0.9982(7) 0.59123(9) -0.0397(2) 0.0370(10) Uani 1 1 d . . . . .
H28 H 0.8793 0.5841 -0.0715 0.044 Uiso 1 1 calc R . . . .
C29 C 1.1777(7) 0.60141(8) -0.0748(2) 0.0358(9) Uani 1 1 d . . . . .
H29 H 1.1809 0.6008 -0.1303 0.043 Uiso 1 1 calc R . . . .
C30 C 1.3542(7) 0.61249(8) -0.0308(2) 0.0332(9) Uani 1 1 d . . . . .
H30 H 1.4766 0.6199 -0.0554 0.040 Uiso 1 1 calc R . . . .
C31 C 1.3459(6) 0.61245(8) 0.0508(2) 0.0263(8) Uani 1 1 d . . . . .
C34 C 1.4895(6) 0.62569(8) 0.11161(19) 0.0252(8) Uani 1 1 d . . . . .
C33 C 1.6405(6) 0.64678(9) 0.1065(2) 0.0344(9) Uani 1 1 d . . . . .
H33 H 1.6909 0.6515 0.0565 0.041 Uiso 1 1 calc R . . . .
C32 C 1.7336(6) 0.66327(10) 0.1767(2) 0.0385(10) Uani 1 1 d . . . . .
H32A H 1.8861 0.6576 0.1858 0.046 Uiso 1 1 calc R . . . .
H32B H 1.7260 0.6855 0.1674 0.046 Uiso 1 1 calc R . . . .
N7 N 1.6167(4) 0.65561(7) 0.24614(17) 0.0279(7) Uani 1 1 d . . . . .
N6 N 1.4021(4) 0.64486(7) 0.23601(16) 0.0262(7) Uani 1 1 d . . . . .
C35 C 1.4053(6) 0.61658(8) 0.18977(19) 0.0245(8) Uani 1 1 d . . . . .
H35 H 1.5008 0.6011 0.2165 0.029 Uiso 1 1 calc R . . . .
C36 C 1.6311(6) 0.67397(8) 0.3106(2) 0.0261(8) Uani 1 1 d . . . . .
C37 C 1.3050(5) 0.64964(8) 0.30674(19) 0.0233(7) Uani 1 1 d . . . . .
C38 C 1.4053(6) 0.68346(8) 0.42265(19) 0.0260(8) Uani 1 1 d . . . . .
C39 C 1.5692(6) 0.68626(8) 0.4798(2) 0.0316(8) Uani 1 1 d . . . . .
H39 H 1.7029 0.6765 0.4738 0.038 Uiso 1 1 calc R . . . .
C40 C 1.5356(7) 0.70349(9) 0.5462(2) 0.0393(10) Uani 1 1 d . . . . .
H40 H 1.6475 0.7058 0.5856 0.047 Uiso 1 1 calc R . . . .
C41 C 1.3390(7) 0.71740(9) 0.5553(2) 0.0418(11) Uani 1 1 d . . . . .
H41 H 1.3173 0.7295 0.6002 0.050 Uiso 1 1 calc R . . . .
C42 C 1.1762(7) 0.71348(9) 0.4989(2) 0.0390(10) Uani 1 1 d . . . . .
H42 H 1.0404 0.7224 0.5059 0.047 Uiso 1 1 calc R . . . .
C43 C 1.2078(6) 0.69656(8) 0.4319(2) 0.0283(8) Uani 1 1 d . . . . .
H43 H 1.0950 0.6940 0.3929 0.034 Uiso 1 1 calc R . . . .
C44 C 1.2295(6) 0.54098(8) 0.1792(2) 0.0267(8) Uani 1 1 d . . . . .
C45 C 1.1089(6) 0.52359(8) 0.1244(2) 0.0301(8) Uani 1 1 d . . . . .
H45 H 0.9649 0.5290 0.1103 0.036 Uiso 1 1 calc R . . . .
C46 C 1.2009(6) 0.49861(9) 0.0913(2) 0.0351(9) Uani 1 1 d . . . . .
H46 H 1.1177 0.4865 0.0549 0.042 Uiso 1 1 calc R . . . .
C47 C 1.4129(7) 0.49056(9) 0.1095(2) 0.0373(10) Uani 1 1 d . . . . .
C48 C 1.5277(7) 0.50796(9) 0.1652(3) 0.0423(10) Uani 1 1 d . . . . .
H48 H 1.6712 0.5025 0.1798 0.051 Uiso 1 1 calc R . . . .
C49 C 1.4387(6) 0.53310(9) 0.2001(2) 0.0355(9) Uani 1 1 d . . . . .
H49 H 1.5202 0.5448 0.2378 0.043 Uiso 1 1 calc R . . . .
C50 C 1.5137(8) 0.46381(10) 0.0715(3) 0.0566(13) Uani 1 1 d . . . . .
H50A H 1.4095 0.4544 0.0340 0.085 Uiso 1 1 calc R . . . .
H50B H 1.6382 0.4707 0.0439 0.085 Uiso 1 1 calc R . . . .
H50C H 1.5594 0.4489 0.1116 0.085 Uiso 1 1 calc R . . . .
Cl2 Cl 0.9035(2) 0.72606(3) 0.72109(7) 0.0583(3) Uani 1 1 d . . . . .
C51 C 1.0553(7) 0.74939(9) 0.7881(2) 0.0462(11) Uani 1 1 d . . . . .
H51A H 0.9604 0.7648 0.8103 0.055 Uiso 1 1 calc R . . . .
H51B H 1.1155 0.7367 0.8318 0.055 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 O3 1.424(3) . ?
S1 O4 1.423(3) . ?
S1 N1 1.676(3) . ?
S1 C19 1.764(4) . ?
O1 C11 1.215(4) . ?
O2 C12 1.199(4) . ?
N1 C1 1.448(4) . ?
N1 C8 1.469(4) . ?
N4 C11 1.394(5) . ?
N4 C12 1.403(4) . ?
N4 C13 1.436(4) . ?
C1 C2 1.373(5) . ?
C1 C6 1.400(5) . ?
C2 H2 0.9500 . ?
C2 C3 1.397(5) . ?
C3 H3 0.9500 . ?
C3 C4 1.375(6) . ?
C4 H4 0.9500 . ?
C4 C5 1.394(6) . ?
C5 H5 0.9500 . ?
C5 C6 1.395(5) . ?
C6 C7 1.455(5) . ?
C7 C9 1.329(5) . ?
C7 C8 1.519(5) . ?
C9 H9 0.9500 . ?
C9 C10 1.487(5) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C10 N3 1.470(4) . ?
N3 N2 1.421(4) . ?
N3 C11 1.363(4) . ?
N2 C8 1.467(4) . ?
N2 C12 1.397(4) . ?
C8 H8 1.0000 . ?
C13 C14 1.378(5) . ?
C13 C18 1.380(5) . ?
C14 H14 0.9500 . ?
C14 C15 1.396(5) . ?
C15 H15 0.9500 . ?
C15 C16 1.387(6) . ?
C16 H16 0.9500 . ?
C16 C17 1.369(6) . ?
C17 H17 0.9500 . ?
C17 C18 1.386(5) . ?
C18 H18 0.9500 . ?
C19 C20 1.396(5) . ?
C19 C24 1.381(5) . ?
C20 H20 0.9500 . ?
C20 C21 1.385(5) . ?
C21 H21 0.9500 . ?
C21 C22 1.391(6) . ?
C22 C23 1.393(6) . ?
C22 C25 1.500(5) . ?
C23 H23 0.9500 . ?
C23 C24 1.382(6) . ?
C24 H24 0.9500 . ?
C25 H25A 0.9800 . ?
C25 H25B 0.9800 . ?
C25 H25C 0.9800 . ?
Cl1 C51 1.746(5) . ?
S2 O7 1.423(3) . ?
S2 O8 1.423(2) . ?
S2 N5 1.679(3) . ?
S2 C44 1.763(4) . ?
O5 C36 1.214(4) . ?
O6 C37 1.201(4) . ?
N5 C26 1.447(4) . ?
N5 C35 1.474(4) . ?
N8 C36 1.392(4) . ?
N8 C37 1.399(4) . ?
N8 C38 1.437(4) . ?
C26 C27 1.375(5) . ?
C26 C31 1.400(5) . ?
C27 H27 0.9500 . ?
C27 C28 1.397(5) . ?
C28 H28 0.9500 . ?
C28 C29 1.377(6) . ?
C29 H29 0.9500 . ?
C29 C30 1.390(6) . ?
C30 H30 0.9500 . ?
C30 C31 1.400(5) . ?
C31 C34 1.457(5) . ?
C34 C33 1.328(5) . ?
C34 C35 1.517(5) . ?
C33 H33 0.9500 . ?
C33 C32 1.492(5) . ?
C32 H32A 0.9900 . ?
C32 H32B 0.9900 . ?
C32 N7 1.467(4) . ?
N7 N6 1.425(4) . ?
N7 C36 1.364(4) . ?
N6 C35 1.471(4) . ?
N6 C37 1.399(4) . ?
C35 H35 1.0000 . ?
C38 C39 1.383(5) . ?
C38 C43 1.380(5) . ?
C39 H39 0.9500 . ?
C39 C40 1.389(5) . ?
C40 H40 0.9500 . ?
C40 C41 1.389(6) . ?
C41 H41 0.9500 . ?
C41 C42 1.375(6) . ?
C42 H42 0.9500 . ?
C42 C43 1.389(5) . ?
C43 H43 0.9500 . ?
C44 C45 1.397(5) . ?
C44 C49 1.382(5) . ?
C45 H45 0.9500 . ?
C45 C46 1.374(5) . ?
C46 H46 0.9500 . ?
C46 C47 1.392(6) . ?
C47 C48 1.390(6) . ?
C47 C50 1.497(6) . ?
C48 H48 0.9500 . ?
C48 C49 1.385(6) . ?
C49 H49 0.9500 . ?
C50 H50A 0.9800 . ?
C50 H50B 0.9800 . ?
C50 H50C 0.9800 . ?
Cl2 C51 1.773(4) . ?
C51 H51A 0.9900 . ?
C51 H51B 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
O3 S1 N1 105.31(14) . . ?
O3 S1 C19 107.89(16) . . ?
O4 S1 O3 121.26(16) . . ?
O4 S1 N1 106.40(15) . . ?
O4 S1 C19 108.60(16) . . ?
N1 S1 C19 106.47(15) . . ?
C1 N1 S1 118.5(2) . . ?
C1 N1 C8 108.8(3) . . ?
C8 N1 S1 116.7(2) . . ?
C11 N4 C12 110.9(3) . . ?
C11 N4 C13 121.7(3) . . ?
C12 N4 C13 126.3(3) . . ?
C2 C1 N1 128.2(3) . . ?
C2 C1 C6 122.1(3) . . ?
C6 C1 N1 109.7(3) . . ?
C1 C2 H2 121.4 . . ?
C1 C2 C3 117.1(4) . . ?
C3 C2 H2 121.4 . . ?
C2 C3 H3 119.1 . . ?
C4 C3 C2 121.8(4) . . ?
C4 C3 H3 119.1 . . ?
C3 C4 H4 119.5 . . ?
C3 C4 C5 121.0(3) . . ?
C5 C4 H4 119.5 . . ?
C4 C5 H5 121.0 . . ?
C4 C5 C6 118.0(4) . . ?
C6 C5 H5 121.0 . . ?
C1 C6 C7 109.0(3) . . ?
C5 C6 C1 120.0(3) . . ?
C5 C6 C7 130.7(3) . . ?
C6 C7 C8 107.1(3) . . ?
C9 C7 C6 130.8(3) . . ?
C9 C7 C8 120.9(3) . . ?
C7 C9 H9 118.9 . . ?
C7 C9 C10 122.2(3) . . ?
C10 C9 H9 118.9 . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
H10A C10 H10B 108.0 . . ?
N3 C10 C9 110.9(3) . . ?
N3 C10 H10A 109.5 . . ?
N3 C10 H10B 109.5 . . ?
N2 N3 C10 119.2(3) . . ?
C11 N3 C10 119.4(3) . . ?
C11 N3 N2 107.7(3) . . ?
N3 N2 C8 108.6(3) . . ?
C12 N2 N3 108.0(3) . . ?
C12 N2 C8 129.5(3) . . ?
N1 C8 C7 104.5(3) . . ?
N1 C8 H8 110.8 . . ?
C7 C8 H8 110.8 . . ?
N2 C8 N1 114.6(3) . . ?
N2 C8 C7 104.9(3) . . ?
N2 C8 H8 110.8 . . ?
O1 C11 N4 126.7(3) . . ?
O1 C11 N3 127.3(3) . . ?
N3 C11 N4 106.0(3) . . ?
O2 C12 N4 127.9(3) . . ?
O2 C12 N2 127.8(3) . . ?
N2 C12 N4 104.3(3) . . ?
C14 C13 N4 118.8(3) . . ?
C14 C13 C18 121.3(3) . . ?
C18 C13 N4 119.7(3) . . ?
C13 C14 H14 120.6 . . ?
C13 C14 C15 118.7(4) . . ?
C15 C14 H14 120.6 . . ?
C14 C15 H15 119.9 . . ?
C16 C15 C14 120.1(4) . . ?
C16 C15 H15 119.9 . . ?
C15 C16 H16 120.0 . . ?
C17 C16 C15 120.1(4) . . ?
C17 C16 H16 120.0 . . ?
C16 C17 H17 119.7 . . ?
C16 C17 C18 120.5(4) . . ?
C18 C17 H17 119.7 . . ?
C13 C18 C17 119.2(4) . . ?
C13 C18 H18 120.4 . . ?
C17 C18 H18 120.4 . . ?
C20 C19 S1 120.2(3) . . ?
C24 C19 S1 119.3(3) . . ?
C24 C19 C20 120.5(3) . . ?
C19 C20 H20 120.5 . . ?
C21 C20 C19 119.1(3) . . ?
C21 C20 H20 120.5 . . ?
C20 C21 H21 119.3 . . ?
C20 C21 C22 121.4(4) . . ?
C22 C21 H21 119.3 . . ?
C21 C22 C23 117.9(4) . . ?
C21 C22 C25 120.7(4) . . ?
C23 C22 C25 121.3(4) . . ?
C22 C23 H23 119.2 . . ?
C24 C23 C22 121.7(4) . . ?
C24 C23 H23 119.2 . . ?
C19 C24 C23 119.3(4) . . ?
C19 C24 H24 120.3 . . ?
C23 C24 H24 120.3 . . ?
C22 C25 H25A 109.5 . . ?
C22 C25 H25B 109.5 . . ?
C22 C25 H25C 109.5 . . ?
H25A C25 H25B 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
O7 S2 O8 121.10(16) . . ?
O7 S2 N5 106.34(15) . . ?
O7 S2 C44 108.49(16) . . ?
O8 S2 N5 105.47(14) . . ?
O8 S2 C44 108.05(17) . . ?
N5 S2 C44 106.52(15) . . ?
C26 N5 S2 117.4(2) . . ?
C26 N5 C35 108.4(3) . . ?
C35 N5 S2 116.8(2) . . ?
C36 N8 C37 111.0(3) . . ?
C36 N8 C38 122.2(3) . . ?
C37 N8 C38 126.0(3) . . ?
C27 C26 N5 128.0(3) . . ?
C27 C26 C31 122.0(3) . . ?
C31 C26 N5 109.9(3) . . ?
C26 C27 H27 121.3 . . ?
C26 C27 C28 117.4(4) . . ?
C28 C27 H27 121.3 . . ?
C27 C28 H28 119.3 . . ?
C29 C28 C27 121.4(4) . . ?
C29 C28 H28 119.3 . . ?
C28 C29 H29 119.3 . . ?
C28 C29 C30 121.4(3) . . ?
C30 C29 H29 119.3 . . ?
C29 C30 H30 121.1 . . ?
C29 C30 C31 117.9(4) . . ?
C31 C30 H30 121.1 . . ?
C26 C31 C34 108.8(3) . . ?
C30 C31 C26 119.9(3) . . ?
C30 C31 C34 131.0(3) . . ?
C31 C34 C35 107.0(3) . . ?
C33 C34 C31 130.1(3) . . ?
C33 C34 C35 121.6(3) . . ?
C34 C33 H33 118.9 . . ?
C34 C33 C32 122.2(3) . . ?
C32 C33 H33 118.9 . . ?
C33 C32 H32A 109.6 . . ?
C33 C32 H32B 109.6 . . ?
H32A C32 H32B 108.1 . . ?
N7 C32 C33 110.5(3) . . ?
N7 C32 H32A 109.6 . . ?
N7 C32 H32B 109.6 . . ?
N6 N7 C32 119.1(3) . . ?
C36 N7 C32 120.3(3) . . ?
C36 N7 N6 108.3(3) . . ?
N7 N6 C35 107.7(3) . . ?
C37 N6 N7 107.3(3) . . ?
C37 N6 C35 127.6(3) . . ?
N5 C35 C34 104.7(3) . . ?
N5 C35 H35 110.7 . . ?
C34 C35 H35 110.7 . . ?
N6 C35 N5 114.3(3) . . ?
N6 C35 C34 105.5(3) . . ?
N6 C35 H35 110.7 . . ?
O5 C36 N8 127.7(3) . . ?
O5 C36 N7 126.6(3) . . ?
N7 C36 N8 105.8(3) . . ?
O6 C37 N8 127.9(3) . . ?
O6 C37 N6 127.1(3) . . ?
N8 C37 N6 104.9(3) . . ?
C39 C38 N8 118.6(3) . . ?
C43 C38 N8 120.2(3) . . ?
C43 C38 C39 121.1(3) . . ?
C38 C39 H39 120.4 . . ?
C38 C39 C40 119.1(4) . . ?
C40 C39 H39 120.4 . . ?
C39 C40 H40 119.8 . . ?
C39 C40 C41 120.3(4) . . ?
C41 C40 H40 119.8 . . ?
C40 C41 H41 120.2 . . ?
C42 C41 C40 119.6(4) . . ?
C42 C41 H41 120.2 . . ?
C41 C42 H42 119.6 . . ?
C41 C42 C43 120.8(4) . . ?
C43 C42 H42 119.6 . . ?
C38 C43 C42 119.1(4) . . ?
C38 C43 H43 120.5 . . ?
C42 C43 H43 120.5 . . ?
C45 C44 S2 120.8(3) . . ?
C49 C44 S2 118.8(3) . . ?
C49 C44 C45 120.4(3) . . ?
C44 C45 H45 120.4 . . ?
C46 C45 C44 119.3(4) . . ?
C46 C45 H45 120.4 . . ?
C45 C46 H46 119.1 . . ?
C45 C46 C47 121.7(4) . . ?
C47 C46 H46 119.1 . . ?
C46 C47 C50 121.4(4) . . ?
C48 C47 C46 117.7(4) . . ?
C48 C47 C50 120.9(4) . . ?
C47 C48 H48 119.1 . . ?
C49 C48 C47 121.8(4) . . ?
C49 C48 H48 119.1 . . ?
C44 C49 C48 119.1(4) . . ?
C44 C49 H49 120.5 . . ?
C48 C49 H49 120.5 . . ?
C47 C50 H50A 109.5 . . ?
C47 C50 H50B 109.5 . . ?
C47 C50 H50C 109.5 . . ?
H50A C50 H50B 109.5 . . ?
H50A C50 H50C 109.5 . . ?
H50B C50 H50C 109.5 . . ?
Cl1 C51 Cl2 111.7(2) . . ?
Cl1 C51 H51A 109.3 . . ?
Cl1 C51 H51B 109.3 . . ?
Cl2 C51 H51A 109.3 . . ?
Cl2 C51 H51B 109.3 . . ?
H51A C51 H51B 107.9 . . ?

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 N1 C1 C2 44.3(4) . . . . ?
S1 N1 C1 C6 -138.2(2) . . . . ?
S1 N1 C8 C7 144.4(2) . . . . ?
S1 N1 C8 N2 -101.4(3) . . . . ?
S1 C19 C20 C21 179.7(3) . . . . ?
S1 C19 C24 C23 -178.9(3) . . . . ?
O3 S1 N1 C1 163.6(3) . . . . ?
O3 S1 N1 C8 30.5(3) . . . . ?
O3 S1 C19 C20 150.9(3) . . . . ?
O3 S1 C19 C24 -29.2(3) . . . . ?
O4 S1 N1 C1 -66.5(3) . . . . ?
O4 S1 N1 C8 160.4(2) . . . . ?
O4 S1 C19 C20 17.8(3) . . . . ?
O4 S1 C19 C24 -162.3(3) . . . . ?
N1 S1 C19 C20 -96.4(3) . . . . ?
N1 S1 C19 C24 83.4(3) . . . . ?
N1 C1 C2 C3 178.7(3) . . . . ?
N1 C1 C6 C5 -178.8(3) . . . . ?
N1 C1 C6 C7 -4.7(4) . . . . ?
N4 C13 C14 C15 174.8(3) . . . . ?
N4 C13 C18 C17 -175.2(3) . . . . ?
C1 N1 C8 C7 7.1(3) . . . . ?
C1 N1 C8 N2 121.3(3) . . . . ?
C1 C2 C3 C4 -0.7(5) . . . . ?
C1 C6 C7 C9 -158.8(4) . . . . ?
C1 C6 C7 C8 9.1(4) . . . . ?
C2 C1 C6 C5 -1.1(5) . . . . ?
C2 C1 C6 C7 173.0(3) . . . . ?
C2 C3 C4 C5 -0.4(6) . . . . ?
C3 C4 C5 C6 0.7(5) . . . . ?
C4 C5 C6 C1 0.0(5) . . . . ?
C4 C5 C6 C7 -172.6(3) . . . . ?
C5 C6 C7 C9 14.4(6) . . . . ?
C5 C6 C7 C8 -177.7(4) . . . . ?
C6 C1 C2 C3 1.4(5) . . . . ?
C6 C7 C9 C10 164.8(4) . . . . ?
C6 C7 C8 N1 -9.8(3) . . . . ?
C6 C7 C8 N2 -130.6(3) . . . . ?
C7 C9 C10 N3 -10.6(5) . . . . ?
C9 C7 C8 N1 159.6(3) . . . . ?
C9 C7 C8 N2 38.7(4) . . . . ?
C9 C10 N3 N2 -17.9(4) . . . . ?
C9 C10 N3 C11 -153.5(3) . . . . ?
C10 N3 N2 C8 57.1(4) . . . . ?
C10 N3 N2 C12 -158.2(3) . . . . ?
C10 N3 C11 O1 -22.6(5) . . . . ?
C10 N3 C11 N4 155.9(3) . . . . ?
N3 N2 C8 N1 -177.0(3) . . . . ?
N3 N2 C8 C7 -63.0(3) . . . . ?
N3 N2 C12 O2 -170.1(3) . . . . ?
N3 N2 C12 N4 12.1(3) . . . . ?
N2 N3 C11 O1 -162.7(3) . . . . ?
N2 N3 C11 N4 15.8(4) . . . . ?
C8 N1 C1 C2 -179.3(3) . . . . ?
C8 N1 C1 C6 -1.7(4) . . . . ?
C8 C7 C9 C10 -1.7(5) . . . . ?
C8 N2 C12 O2 -35.4(6) . . . . ?
C8 N2 C12 N4 146.8(3) . . . . ?
C11 N4 C12 O2 179.8(3) . . . . ?
C11 N4 C12 N2 -2.4(4) . . . . ?
C11 N4 C13 C14 -52.3(5) . . . . ?
C11 N4 C13 C18 124.5(4) . . . . ?
C11 N3 N2 C8 -162.6(3) . . . . ?
C11 N3 N2 C12 -17.9(4) . . . . ?
C12 N4 C11 O1 170.0(3) . . . . ?
C12 N4 C11 N3 -8.5(4) . . . . ?
C12 N4 C13 C14 140.6(4) . . . . ?
C12 N4 C13 C18 -42.7(5) . . . . ?
C12 N2 C8 N1 48.5(5) . . . . ?
C12 N2 C8 C7 162.4(3) . . . . ?
C13 N4 C11 O1 1.1(5) . . . . ?
C13 N4 C11 N3 -177.4(3) . . . . ?
C13 N4 C12 O2 -11.9(6) . . . . ?
C13 N4 C12 N2 165.9(3) . . . . ?
C13 C14 C15 C16 1.2(6) . . . . ?
C14 C13 C18 C17 1.4(6) . . . . ?
C14 C15 C16 C17 -0.3(6) . . . . ?
C15 C16 C17 C18 -0.2(6) . . . . ?
C16 C17 C18 C13 -0.4(6) . . . . ?
C18 C13 C14 C15 -1.9(6) . . . . ?
C19 S1 N1 C1 49.2(3) . . . . ?
C19 S1 N1 C8 -83.9(3) . . . . ?
C19 C20 C21 C22 -1.5(5) . . . . ?
C20 C19 C24 C23 1.0(5) . . . . ?
C20 C21 C22 C23 2.3(5) . . . . ?
C20 C21 C22 C25 -178.3(3) . . . . ?
C21 C22 C23 C24 -1.4(6) . . . . ?
C22 C23 C24 C19 -0.2(6) . . . . ?
C24 C19 C20 C21 -0.2(5) . . . . ?
C25 C22 C23 C24 179.2(4) . . . . ?
S2 N5 C26 C27 46.7(5) . . . . ?
S2 N5 C26 C31 -135.7(3) . . . . ?
S2 N5 C35 C34 142.5(2) . . . . ?
S2 N5 C35 N6 -102.6(3) . . . . ?
S2 C44 C45 C46 179.4(3) . . . . ?
S2 C44 C49 C48 -178.9(3) . . . . ?
O7 S2 N5 C26 -68.2(3) . . . . ?
O7 S2 N5 C35 160.5(2) . . . . ?
O7 S2 C44 C45 18.7(3) . . . . ?
O7 S2 C44 C49 -161.6(3) . . . . ?
O8 S2 N5 C26 162.1(3) . . . . ?
O8 S2 N5 C35 30.8(3) . . . . ?
O8 S2 C44 C45 151.7(3) . . . . ?
O8 S2 C44 C49 -28.6(3) . . . . ?
N5 S2 C44 C45 -95.4(3) . . . . ?
N5 S2 C44 C49 84.3(3) . . . . ?
N5 C26 C27 C28 179.8(3) . . . . ?
N5 C26 C31 C30 -180.0(3) . . . . ?
N5 C26 C31 C34 -6.6(4) . . . . ?
N8 C38 C39 C40 174.0(3) . . . . ?
N8 C38 C43 C42 -174.6(3) . . . . ?
C26 N5 C35 C34 7.2(3) . . . . ?
C26 N5 C35 N6 122.0(3) . . . . ?
C26 C27 C28 C29 -0.8(5) . . . . ?
C26 C31 C34 C33 -155.9(4) . . . . ?
C26 C31 C34 C35 11.0(4) . . . . ?
C27 C26 C31 C30 -2.1(5) . . . . ?
C27 C26 C31 C34 171.2(3) . . . . ?
C27 C28 C29 C30 -1.0(6) . . . . ?
C28 C29 C30 C31 1.2(5) . . . . ?
C29 C30 C31 C26 0.3(5) . . . . ?
C29 C30 C31 C34 -171.4(3) . . . . ?
C30 C31 C34 C33 16.5(6) . . . . ?
C30 C31 C34 C35 -176.6(4) . . . . ?
C31 C26 C27 C28 2.4(5) . . . . ?
C31 C34 C33 C32 164.0(4) . . . . ?
C31 C34 C35 N5 -11.0(3) . . . . ?
C31 C34 C35 N6 -131.9(3) . . . . ?
C34 C33 C32 N7 -7.2(6) . . . . ?
C33 C34 C35 N5 157.3(3) . . . . ?
C33 C34 C35 N6 36.4(4) . . . . ?
C33 C32 N7 N6 -23.3(5) . . . . ?
C33 C32 N7 C36 -161.1(3) . . . . ?
C32 N7 N6 C35 60.4(4) . . . . ?
C32 N7 N6 C37 -159.3(3) . . . . ?
C32 N7 C36 O5 -20.9(6) . . . . ?
C32 N7 C36 N8 157.2(3) . . . . ?
N7 N6 C35 N5 -176.3(3) . . . . ?
N7 N6 C35 C34 -61.9(3) . . . . ?
N7 N6 C37 O6 -171.4(3) . . . . ?
N7 N6 C37 N8 11.0(3) . . . . ?
N6 N7 C36 O5 -162.7(3) . . . . ?
N6 N7 C36 N8 15.4(4) . . . . ?
C35 N5 C26 C27 -178.3(3) . . . . ?
C35 N5 C26 C31 -0.6(4) . . . . ?
C35 C34 C33 C32 -1.3(6) . . . . ?
C35 N6 C37 O6 -41.6(6) . . . . ?
C35 N6 C37 N8 140.9(3) . . . . ?
C36 N8 C37 O6 -179.2(3) . . . . ?
C36 N8 C37 N6 -1.7(4) . . . . ?
C36 N8 C38 C39 -45.6(5) . . . . ?
C36 N8 C38 C43 130.8(4) . . . . ?
C36 N7 N6 C35 -157.3(3) . . . . ?
C36 N7 N6 C37 -17.0(4) . . . . ?
C37 N8 C36 O5 169.5(3) . . . . ?
C37 N8 C36 N7 -8.7(4) . . . . ?
C37 N8 C38 C39 144.8(3) . . . . ?
C37 N8 C38 C43 -38.8(5) . . . . ?
C37 N6 C35 N5 54.0(4) . . . . ?
C37 N6 C35 C34 168.4(3) . . . . ?
C38 N8 C36 O5 -1.5(6) . . . . ?
C38 N8 C36 N7 -179.6(3) . . . . ?
C38 N8 C37 O6 -8.7(6) . . . . ?
C38 N8 C37 N6 168.8(3) . . . . ?
C38 C39 C40 C41 0.8(6) . . . . ?
C39 C38 C43 C42 1.7(5) . . . . ?
C39 C40 C41 C42 1.4(6) . . . . ?
C40 C41 C42 C43 -2.0(6) . . . . ?
C41 C42 C43 C38 0.5(6) . . . . ?
C43 C38 C39 C40 -2.3(5) . . . . ?
C44 S2 N5 C26 47.4(3) . . . . ?
C44 S2 N5 C35 -83.9(3) . . . . ?
C44 C45 C46 C47 -1.5(6) . . . . ?
C45 C44 C49 C48 0.8(5) . . . . ?
C45 C46 C47 C48 2.6(6) . . . . ?
C45 C46 C47 C50 -178.3(4) . . . . ?
C46 C47 C48 C49 -2.0(6) . . . . ?
C47 C48 C49 C44 0.4(6) . . . . ?
C49 C44 C45 C46 -0.3(5) . . . . ?
C50 C47 C48 C49 178.9(4) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_mjh140029_fa
_database_code_depnum_ccdc_archive 'CCDC 1040306'
_audit_update_record             
;
2014-12-18 deposited with the CCDC.
2015-01-16 downloaded from the CCDC.
;
_audit_creation_date             2014-12-18
_audit_creation_method           
;
Olex2 1.2-alpha
(compiled 2014.12.09 svn.r3114 for OlexSys, GUI svn.r4963)
;
_shelxl_version_number           2014/6
_chemical_name_common            ?
_chemical_name_systematic        
'ethyl 3-((3aS*,4R*,10aS*,10bS*)-1,3-dioxo-10-tosyl-1,2,3,3a,4,10,10a,10b-octahydropyrrolo[3,4-a]carbazol-4-yl)propanoate'
_chemical_formula_moiety         'C26 H26 N2 O6 S'
_chemical_formula_sum            'C26 H26 N2 O6 S'
_chemical_formula_weight         494.55
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C26 H26 N2 O6 S1'
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                   16.0840(2)
_cell_length_b                   8.84163(10)
_cell_length_c                   18.0999(2)
_cell_angle_alpha                90
_cell_angle_beta                 106.2054(14)
_cell_angle_gamma                90
_cell_volume                     2471.70(6)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    27003
_cell_measurement_temperature    150.0
_cell_measurement_theta_max      66.6150
_cell_measurement_theta_min      2.4920
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    1.537
_exptl_absorpt_correction_T_max  0.827
_exptl_absorpt_correction_T_min  0.691
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
Analytical numeric absorption correction using a multifaceted crystal
			model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.329
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_F_000             1040
_exptl_crystal_size_max          0.2871
_exptl_crystal_size_mid          0.2849
_exptl_crystal_size_min          0.1359
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0518
_diffrn_reflns_av_unetI/netI     0.0153
_diffrn_reflns_Laue_measured_fraction_full 0.981
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            65129
_diffrn_reflns_point_group_measured_fraction_full 0.981
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        67.500
_diffrn_reflns_theta_max         66.780
_diffrn_reflns_theta_min         3.255
_diffrn_ambient_temperature      150.00(10)
_diffrn_detector_area_resol_mean 10.3968
_diffrn_measured_fraction_theta_full 0.981
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega   -1.00   25.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       34.0000   81.0000  -95.5864 26

#__ type_ start__ end____ width___ exp.time_
  2 omega  -97.00  -18.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -41.9655  125.0000 -120.0000 79

#__ type_ start__ end____ width___ exp.time_
  3 omega   24.00  115.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       41.9655   38.0000    0.0000 91

#__ type_ start__ end____ width___ exp.time_
  4 omega   17.00   62.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       41.9655   38.0000 -120.0000 45

#__ type_ start__ end____ width___ exp.time_
  5 omega   69.00   95.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       41.9655   38.0000 -120.0000 26

#__ type_ start__ end____ width___ exp.time_
  6 omega   -3.00   95.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       41.9655 -125.0000  120.0000 98

#__ type_ start__ end____ width___ exp.time_
  7 omega   16.00  118.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       41.9655   38.0000   90.0000 102

#__ type_ start__ end____ width___ exp.time_
  8 omega    8.00   48.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       41.9655   77.0000  120.0000 40

#__ type_ start__ end____ width___ exp.time_
  9 omega   13.00   55.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       46.0000   78.0000 -163.1291 42

#__ type_ start__ end____ width___ exp.time_
 10 omega   18.00   47.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       50.0000   77.0000   58.0560 29

#__ type_ start__ end____ width___ exp.time_
 11 omega   21.00   48.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000   77.0000   -2.2956 27

#__ type_ start__ end____ width___ exp.time_
 12 omega   69.00   96.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000   79.0000 -113.7120 27

#__ type_ start__ end____ width___ exp.time_
 13 omega   20.00   66.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000   79.0000 -113.7120 46

#__ type_ start__ end____ width___ exp.time_
 14 omega   28.00  116.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       62.0000   77.0000  107.6284 88

#__ type_ start__ end____ width___ exp.time_
 15 omega   28.00   56.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       62.0000   78.0000  -55.8555 28

#__ type_ start__ end____ width___ exp.time_
 16 omega   33.00   58.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       66.0000   79.0000 -145.9565 25

#__ type_ start__ end____ width___ exp.time_
 17 omega   35.00   68.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       66.0000   77.0000 -113.6783 33

#__ type_ start__ end____ width___ exp.time_
 18 omega   33.00   58.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       66.0000   78.0000   24.9463 25

#__ type_ start__ end____ width___ exp.time_
 19 omega   32.00   59.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       66.0000   77.0000   68.9710 27

#__ type_ start__ end____ width___ exp.time_
 20 omega   32.00   58.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       66.0000   79.0000  163.3776 26

#__ type_ start__ end____ width___ exp.time_
 21 omega  105.00  131.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       66.0000   79.0000   -0.4747 26

#__ type_ start__ end____ width___ exp.time_
 22 omega   33.00   59.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       66.0000   79.0000   -0.4747 26

#__ type_ start__ end____ width___ exp.time_
 23 omega   36.00   86.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       70.0000   79.0000  -99.6759 50

#__ type_ start__ end____ width___ exp.time_
 24 omega   36.00   62.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       70.0000   79.0000  -41.7725 26

#__ type_ start__ end____ width___ exp.time_
 25 omega   36.00   69.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       70.0000   79.0000  133.7798 33

#__ type_ start__ end____ width___ exp.time_
 26 omega   61.00  109.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000   72.0000   22.6431 48

#__ type_ start__ end____ width___ exp.time_
 27 omega   60.00  145.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000   77.0000  120.0000 85

#__ type_ start__ end____ width___ exp.time_
 28 omega  118.00  154.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000  -15.0000    0.0000 36

#__ type_ start__ end____ width___ exp.time_
 29 omega   60.00  120.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000   77.0000  -60.0000 60

#__ type_ start__ end____ width___ exp.time_
 30 omega  140.00  165.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000   77.0000  -60.0000 25

#__ type_ start__ end____ width___ exp.time_
 31 omega  117.00  170.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000   77.0000  150.0000 53

#__ type_ start__ end____ width___ exp.time_
 32 omega   60.00   98.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000   77.0000  150.0000 38

#__ type_ start__ end____ width___ exp.time_
 33 omega   74.00  146.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000   61.0000    0.0000 72

#__ type_ start__ end____ width___ exp.time_
 34 omega   89.00  126.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000   61.0000  -30.0000 37

#__ type_ start__ end____ width___ exp.time_
 35 omega   45.00   74.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000  -94.0000  -30.0000 29

#__ type_ start__ end____ width___ exp.time_
 36 omega   60.00  130.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000   77.0000   30.0000 70

#__ type_ start__ end____ width___ exp.time_
 37 omega  118.00  171.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000   77.0000  -30.0000 53

#__ type_ start__ end____ width___ exp.time_
 38 omega   60.00   88.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000   77.0000  -30.0000 28

#__ type_ start__ end____ width___ exp.time_
 39 omega   17.00   61.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000  -30.0000  -60.0000 44

#__ type_ start__ end____ width___ exp.time_
 40 omega   77.00  131.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000  -90.0000  -82.8062 54

#__ type_ start__ end____ width___ exp.time_
 41 omega   21.00  124.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000  -61.0000  150.0000 103

#__ type_ start__ end____ width___ exp.time_
 42 omega   60.00  159.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000   77.0000   60.0000 99

#__ type_ start__ end____ width___ exp.time_
 43 omega    9.00   58.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000  -90.0000  -82.8062 49

#__ type_ start__ end____ width___ exp.time_
 44 omega   54.00   80.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000  -55.0000  -36.0000 26

#__ type_ start__ end____ width___ exp.time_
 45 omega   60.00  171.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000   77.0000 -120.0000 111

#__ type_ start__ end____ width___ exp.time_
 46 omega   60.00   99.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000   77.0000 -150.0000 39

#__ type_ start__ end____ width___ exp.time_
 47 omega   13.00  127.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000  -93.0000   76.0221 114

#__ type_ start__ end____ width___ exp.time_
 48 omega   22.00   48.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000  -55.0000  -36.0000 26

#__ type_ start__ end____ width___ exp.time_
 49 omega  133.00  164.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000   77.0000 -180.0000 31

#__ type_ start__ end____ width___ exp.time_
 50 omega  131.00  161.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000   61.0000  -30.0000 30

#__ type_ start__ end____ width___ exp.time_
 51 omega  100.00  126.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000  -92.0000  -48.8347 26

#__ type_ start__ end____ width___ exp.time_
 52 omega   61.00  104.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000   77.0000 -180.0000 43

#__ type_ start__ end____ width___ exp.time_
 53 omega   43.00   69.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000  -15.0000    0.0000 26

#__ type_ start__ end____ width___ exp.time_
 54 omega   74.00  100.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000  -15.0000    0.0000 26

#__ type_ start__ end____ width___ exp.time_
 55 omega  126.00  168.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000   77.0000    0.0000 42

#__ type_ start__ end____ width___ exp.time_
 56 omega   13.00   59.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000  -92.0000  -48.8347 46

#__ type_ start__ end____ width___ exp.time_
 57 omega  106.00  132.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000  125.0000  120.0000 26

#__ type_ start__ end____ width___ exp.time_
 58 omega  139.00  164.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000  125.0000  120.0000 25

#__ type_ start__ end____ width___ exp.time_
 59 omega   60.00  105.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000   77.0000    0.0000 45

#__ type_ start__ end____ width___ exp.time_
 60 omega   92.00  161.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000   77.0000   90.0000 69

#__ type_ start__ end____ width___ exp.time_
 61 omega   28.00  113.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000  -61.0000   60.0000 85

#__ type_ start__ end____ width___ exp.time_
 62 omega   72.00  152.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000   30.0000 -150.0000 80

#__ type_ start__ end____ width___ exp.time_
 63 omega   68.00  131.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000  -92.0000  179.2320 63

#__ type_ start__ end____ width___ exp.time_
 64 omega   73.00  148.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000   45.0000 -120.0000 75

#__ type_ start__ end____ width___ exp.time_
 65 omega   60.00   87.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000   77.0000   90.0000 27

#__ type_ start__ end____ width___ exp.time_
 66 omega   60.00  171.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000   77.0000  -90.0000 111

#__ type_ start__ end____ width___ exp.time_
 67 omega  116.00  170.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000   72.0000   22.6431 54

#__ type_ start__ end____ width___ exp.time_
 68 omega  -99.00  -18.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -41.9655  125.0000   90.0000 81

#__ type_ start__ end____ width___ exp.time_
 69 omega    8.00  110.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       41.9655   77.0000  -60.0000 102

#__ type_ start__ end____ width___ exp.time_
 70 omega   24.00  137.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       58.0000   77.0000  129.1963 113

#__ type_ start__ end____ width___ exp.time_
 71 omega   28.00  142.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       62.0000   79.0000 -158.2146 114

#__ type_ start__ end____ width___ exp.time_
 72 omega   32.00  146.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       66.0000   79.0000   -0.4747 114

#__ type_ start__ end____ width___ exp.time_
 73 omega   32.00  146.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       66.0000   79.0000  -99.9803 114

#__ type_ start__ end____ width___ exp.time_
 74 omega   32.00  146.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       66.0000   79.0000  -59.7422 114

#__ type_ start__ end____ width___ exp.time_
 75 omega   32.00  145.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       66.0000   77.0000  140.6230 113

#__ type_ start__ end____ width___ exp.time_
 76 omega   32.00  145.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       66.0000   77.0000   68.9710 113
;
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini ultra'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0453515000
_diffrn_orient_matrix_UB_12      -0.1356481000
_diffrn_orient_matrix_UB_13      -0.0480744000
_diffrn_orient_matrix_UB_21      0.0770528000
_diffrn_orient_matrix_UB_22      -0.0177926000
_diffrn_orient_matrix_UB_23      -0.0342331000
_diffrn_orient_matrix_UB_31      0.0442803000
_diffrn_orient_matrix_UB_32      -0.1078758000
_diffrn_orient_matrix_UB_33      0.0661186000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Enhance Ultra (Cu) X-ray Source'
_diffrn_special_details          ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3952
_reflns_number_total             4373
_reflns_odcompleteness_completeness 99.94
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.49
_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 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XT (Sheldrick, 2008)'
_refine_diff_density_max         0.317
_refine_diff_density_min         -0.480
_refine_diff_density_rms         0.059
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     341
_refine_ls_number_reflns         4373
_refine_ls_number_restraints     345
_refine_ls_R_factor_all          0.0392
_refine_ls_R_factor_gt           0.0351
_refine_ls_restrained_S_all      0.995
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0479P)²+1.5257P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0896
_refine_ls_wR_factor_ref         0.0929
_refine_special_details          
;
The terminal ethoxy group is positionally
 disordered over 3 positions. The site occupancy
 factors have been fixed at values determined
 from an isotropic refinement of these groups, to
 give a summed value of unity.
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 O4B-C17 \\sim O4C-C17 \\sim O4A-C17
 with sigma of 0.01
 O4B-C18B \\sim O4C-C18C \\sim O4A-C18A
 with sigma of 0.01
 C19B-C18B \\sim C19C-C18C \\sim C19A-C18A
 with sigma of 0.01
3. Uiso/Uaniso restraints and constraints
Uanis(C18A) = Uanis(C18C) = Uanis(C18B)
Uanis(C19A) = Uanis(C19C) = Uanis(C19B)
Uanis(O4A) = Uanis(O4C) = Uanis(O4B)
4. Rigid body (RIGU) restrains
 All non-hydrogen atoms
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
5. Others
 Fixed Sof: O4B(0.18) C18B(0.18) H18A(0.18) H18B(0.18) C19B(0.18) H19A(0.18)
 H19B(0.18) H19C(0.18) O4A(0.4) C18A(0.4) H18C(0.4) H18D(0.4) C19A(0.4)
 H19D(0.4) H19E(0.4) H19F(0.4) O4C(0.42) C18C(0.42) H18E(0.42) H18F(0.42)
 C19C(0.42) H19G(0.42) H19H(0.42) H19I(0.42)
6.a Ternary CH refined with riding coordinates:
 C8(H8), C9(H9), C10(H10), C11(H11)
6.b Secondary CH2 refined with riding coordinates:
 C15(H15A,H15B), C16(H16A,H16B), C18B(H18A,H18B), C18A(H18C,H18D), C18C(H18E,
 H18F)
6.c Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C5(H5), C6(H6), C12(H12), C21(H21), C22(H22), C24(H24),
 C25(H25)
6.d Idealised Me refined as rotating group:
 C26(H26A,H26B,H26C), C19B(H19A,H19B,H19C), C19A(H19D,H19E,H19F), C19C(H19G,
 H19H,H19I)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_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 0.39651(2) 0.08889(4) 0.61943(2) 0.01796(11) Uani 1 1 d . U . . .
O1 O 0.48495(8) 0.28866(14) 0.82183(7) 0.0321(3) Uani 1 1 d . U . . .
O2 O 0.34213(7) 0.72363(13) 0.84233(6) 0.0279(3) Uani 1 1 d . U . . .
O3 O 0.06187(9) 0.84636(16) 0.46848(8) 0.0435(3) Uani 1 1 d . U . . .
O5 O 0.46883(7) -0.00572(12) 0.61980(6) 0.0237(2) Uani 1 1 d . U . . .
O6 O 0.34038(7) 0.04995(12) 0.66542(6) 0.0232(2) Uani 1 1 d . U . . .
N1 N 0.43571(8) 0.25737(14) 0.64937(7) 0.0179(3) Uani 1 1 d . U . . .
N2 N 0.42681(9) 0.51408(16) 0.84553(8) 0.0237(3) Uani 1 1 d . U . . .
H2 H 0.4640(13) 0.535(2) 0.8846(12) 0.028 Uiso 1 1 d R . . . .
C1 C 0.50160(9) 0.32770(17) 0.62169(8) 0.0182(3) Uani 1 1 d . U . . .
C2 C 0.48863(10) 0.48350(17) 0.61618(8) 0.0186(3) Uani 1 1 d . U . . .
C3 C 0.54730(10) 0.57617(19) 0.59435(9) 0.0239(3) Uani 1 1 d . U . . .
H3 H 0.5391 0.6826 0.5913 0.029 Uiso 1 1 calc R . . . .
C4 C 0.61796(11) 0.5110(2) 0.57710(10) 0.0274(4) Uani 1 1 d . U . . .
H4 H 0.6584 0.5728 0.5615 0.033 Uiso 1 1 calc R . . . .
C5 C 0.62983(10) 0.3555(2) 0.58253(9) 0.0271(4) Uani 1 1 d . U . . .
H5 H 0.6784 0.3123 0.5702 0.032 Uiso 1 1 calc R . . . .
C6 C 0.57258(10) 0.26142(19) 0.60544(9) 0.0228(3) Uani 1 1 d . U . . .
H6 H 0.5817 0.1553 0.6098 0.027 Uiso 1 1 calc R . . . .
C7 C 0.41053(9) 0.52102(17) 0.63814(8) 0.0176(3) Uani 1 1 d . U . . .
C8 C 0.37157(9) 0.37478(16) 0.65563(8) 0.0169(3) Uani 1 1 d . U . . .
H8 H 0.3164 0.3562 0.6144 0.020 Uiso 1 1 calc R . . . .
C9 C 0.35069(9) 0.38523(16) 0.73360(8) 0.0176(3) Uani 1 1 d . U . . .
H9 H 0.3125 0.2984 0.7381 0.021 Uiso 1 1 calc R . . . .
C10 C 0.30329(9) 0.53492(17) 0.74001(8) 0.0179(3) Uani 1 1 d . U . . .
H10 H 0.2444 0.5109 0.7451 0.022 Uiso 1 1 calc R . . . .
C11 C 0.29436(9) 0.65308(17) 0.67469(9) 0.0191(3) Uani 1 1 d . U . . .
H11 H 0.2902 0.7550 0.6974 0.023 Uiso 1 1 calc R . . . .
C12 C 0.37496(9) 0.65277(17) 0.64775(8) 0.0184(3) Uani 1 1 d . U . . .
H12 H 0.4000 0.7452 0.6378 0.022 Uiso 1 1 calc R . . . .
C13 C 0.43001(10) 0.38523(18) 0.80340(9) 0.0208(3) Uani 1 1 d . U . . .
C14 C 0.35711(10) 0.60561(18) 0.81455(9) 0.0206(3) Uani 1 1 d . U . . .
C15 C 0.21124(10) 0.62971(18) 0.60881(9) 0.0231(3) Uani 1 1 d . U . . .
H15A H 0.2158 0.5346 0.5813 0.028 Uiso 1 1 calc R . . . .
H15B H 0.1611 0.6207 0.6302 0.028 Uiso 1 1 calc R . . . .
C16 C 0.19674(11) 0.7619(2) 0.55242(9) 0.0282(4) Uani 1 1 d . U . . .
H16A H 0.1940 0.8566 0.5808 0.034 Uiso 1 1 calc R . . . .
H16B H 0.2471 0.7695 0.5313 0.034 Uiso 1 1 calc R . . . .
C17 C 0.11583(13) 0.7488(2) 0.48683(10) 0.0363(4) Uani 1 1 d D U . . .
C20 C 0.33259(10) 0.10906(16) 0.52371(9) 0.0196(3) Uani 1 1 d . U . . .
C21 C 0.37090(10) 0.09008(17) 0.46440(9) 0.0224(3) Uani 1 1 d . U . . .
H21 H 0.4306 0.0654 0.4754 0.027 Uiso 1 1 calc R . . . .
C22 C 0.32120(11) 0.10750(19) 0.38929(9) 0.0276(4) Uani 1 1 d . U . . .
H22 H 0.3472 0.0936 0.3486 0.033 Uiso 1 1 calc R . . . .
C23 C 0.23389(12) 0.1450(2) 0.37181(10) 0.0333(4) Uani 1 1 d . U . . .
C24 C 0.19677(11) 0.1634(2) 0.43249(10) 0.0325(4) Uani 1 1 d . U . . .
H24 H 0.1372 0.1888 0.4215 0.039 Uiso 1 1 calc R . . . .
C25 C 0.24508(10) 0.14545(19) 0.50799(9) 0.0247(3) Uani 1 1 d . U . . .
H25 H 0.2190 0.1577 0.5487 0.030 Uiso 1 1 calc R . . . .
C26 C 0.18162(14) 0.1674(3) 0.28957(12) 0.0558(6) Uani 1 1 d . U . . .
H26A H 0.2168 0.2205 0.2614 0.084 Uiso 1 1 calc GR . . . .
H26B H 0.1300 0.2277 0.2881 0.084 Uiso 1 1 calc GR . . . .
H26C H 0.1640 0.0688 0.2656 0.084 Uiso 1 1 calc GR . . . .
O4B O 0.1328(7) 0.6468(11) 0.4379(6) 0.0386(14) Uani 0.18 1 d D U P A 1
C18B C 0.0615(10) 0.6278(19) 0.3675(7) 0.0483(17) Uani 0.18 1 d D U P A 1
H18A H 0.0072 0.6692 0.3749 0.058 Uiso 0.18 1 calc R . P A 1
H18B H 0.0526 0.5192 0.3543 0.058 Uiso 0.18 1 calc R . P A 1
C19B C 0.0856(15) 0.711(2) 0.3049(9) 0.0710(19) Uani 0.18 1 d D U P A 1
H19A H 0.0384 0.7032 0.2572 0.107 Uiso 0.18 1 calc GR . P A 1
H19B H 0.1384 0.6669 0.2971 0.107 Uiso 0.18 1 calc GR . P A 1
H19C H 0.0958 0.8177 0.3193 0.107 Uiso 0.18 1 calc GR . P A 1
O4A O 0.0995(5) 0.6038(7) 0.4622(4) 0.0386(14) Uani 0.4 1 d D U P A 2
C18A C 0.0203(5) 0.5705(10) 0.4012(4) 0.0483(17) Uani 0.4 1 d D U P A 2
H18C H -0.0279 0.6327 0.4086 0.058 Uiso 0.4 1 calc R . P A 2
H18D H 0.0048 0.4627 0.4038 0.058 Uiso 0.4 1 calc R . P A 2
C19A C 0.0330(6) 0.6037(10) 0.3237(4) 0.0710(19) Uani 0.4 1 d D U P A 2
H19D H -0.0189 0.5738 0.2834 0.107 Uiso 0.4 1 calc GR . P A 2
H19E H 0.0830 0.5468 0.3177 0.107 Uiso 0.4 1 calc GR . P A 2
H19F H 0.0433 0.7122 0.3196 0.107 Uiso 0.4 1 calc GR . P A 2
O4C O 0.1162(4) 0.6164(6) 0.4480(3) 0.0386(14) Uani 0.42 1 d D U P A 3
C18C C 0.0439(4) 0.5890(9) 0.3794(3) 0.0483(17) Uani 0.42 1 d D U P A 3
H18E H -0.0089 0.6398 0.3847 0.058 Uiso 0.42 1 calc R . P A 3
H18F H 0.0322 0.4791 0.3730 0.058 Uiso 0.42 1 calc R . P A 3
C19C C 0.0677(6) 0.6499(10) 0.3109(3) 0.0710(19) Uani 0.42 1 d D U P A 3
H19G H 0.0192 0.6352 0.2647 0.107 Uiso 0.42 1 calc GR . P A 3
H19H H 0.1187 0.5963 0.3049 0.107 Uiso 0.42 1 calc GR . P A 3
H19I H 0.0806 0.7581 0.3182 0.107 Uiso 0.42 1 calc GR . P A 3


_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 O5 1.4312(11) . ?
S1 O6 1.4304(11) . ?
S1 N1 1.6491(13) . ?
S1 C20 1.7596(16) . ?
O1 C13 1.2069(19) . ?
O2 C14 1.2113(19) . ?
O3 C17 1.203(2) . ?
N1 C1 1.4342(19) . ?
N1 C8 1.4900(18) . ?
N2 H2 0.81(2) . ?
N2 C13 1.380(2) . ?
N2 C14 1.369(2) . ?
C1 C2 1.393(2) . ?
C1 C6 1.386(2) . ?
C2 C3 1.388(2) . ?
C2 C7 1.458(2) . ?
C3 H3 0.9500 . ?
C3 C4 1.385(2) . ?
C4 H4 0.9500 . ?
C4 C5 1.388(2) . ?
C5 H5 0.9500 . ?
C5 C6 1.387(2) . ?
C6 H6 0.9500 . ?
C7 C8 1.508(2) . ?
C7 C12 1.330(2) . ?
C8 H8 1.0000 . ?
C8 C9 1.5419(19) . ?
C9 H9 1.0000 . ?
C9 C10 1.548(2) . ?
C9 C13 1.524(2) . ?
C10 H10 1.0000 . ?
C10 C11 1.554(2) . ?
C10 C14 1.519(2) . ?
C11 H11 1.0000 . ?
C11 C12 1.507(2) . ?
C11 C15 1.537(2) . ?
C12 H12 0.9500 . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C15 C16 1.526(2) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C16 C17 1.501(2) . ?
C17 O4B 1.344(7) . ?
C17 O4A 1.359(6) . ?
C17 O4C 1.366(5) . ?
C20 C21 1.389(2) . ?
C20 C25 1.394(2) . ?
C21 H21 0.9500 . ?
C21 C22 1.380(2) . ?
C22 H22 0.9500 . ?
C22 C23 1.391(2) . ?
C23 C24 1.398(3) . ?
C23 C26 1.504(3) . ?
C24 H24 0.9500 . ?
C24 C25 1.380(2) . ?
C25 H25 0.9500 . ?
C26 H26A 0.9800 . ?
C26 H26B 0.9800 . ?
C26 H26C 0.9800 . ?
O4B C18B 1.466(8) . ?
C18B H18A 0.9900 . ?
C18B H18B 0.9900 . ?
C18B C19B 1.490(11) . ?
C19B H19A 0.9800 . ?
C19B H19B 0.9800 . ?
C19B H19C 0.9800 . ?
O4A C18A 1.465(6) . ?
C18A H18C 0.9900 . ?
C18A H18D 0.9900 . ?
C18A C19A 1.501(8) . ?
C19A H19D 0.9800 . ?
C19A H19E 0.9800 . ?
C19A H19F 0.9800 . ?
O4C C18C 1.466(5) . ?
C18C H18E 0.9900 . ?
C18C H18F 0.9900 . ?
C18C C19C 1.495(8) . ?
C19C H19G 0.9800 . ?
C19C H19H 0.9800 . ?
C19C H19I 0.9800 . ?

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
O5 S1 N1 106.90(6) . . ?
O5 S1 C20 108.33(7) . . ?
O6 S1 O5 120.05(7) . . ?
O6 S1 N1 105.77(6) . . ?
O6 S1 C20 107.88(7) . . ?
N1 S1 C20 107.26(7) . . ?
C1 N1 S1 121.93(10) . . ?
C1 N1 C8 108.62(11) . . ?
C8 N1 S1 116.42(10) . . ?
C13 N2 H2 122.8(14) . . ?
C14 N2 H2 122.7(14) . . ?
C14 N2 C13 114.47(13) . . ?
C2 C1 N1 110.09(13) . . ?
C6 C1 N1 128.58(14) . . ?
C6 C1 C2 121.24(14) . . ?
C1 C2 C7 109.19(13) . . ?
C3 C2 C1 120.29(14) . . ?
C3 C2 C7 130.50(14) . . ?
C2 C3 H3 120.5 . . ?
C4 C3 C2 118.96(15) . . ?
C4 C3 H3 120.5 . . ?
C3 C4 H4 120.0 . . ?
C3 C4 C5 120.09(15) . . ?
C5 C4 H4 120.0 . . ?
C4 C5 H5 119.1 . . ?
C6 C5 C4 121.70(15) . . ?
C6 C5 H5 119.1 . . ?
C1 C6 C5 117.70(15) . . ?
C1 C6 H6 121.2 . . ?
C5 C6 H6 121.2 . . ?
C2 C7 C8 107.59(12) . . ?
C12 C7 C2 132.04(14) . . ?
C12 C7 C8 120.27(13) . . ?
N1 C8 C7 104.14(11) . . ?
N1 C8 H8 108.5 . . ?
N1 C8 C9 116.33(12) . . ?
C7 C8 H8 108.5 . . ?
C7 C8 C9 110.49(12) . . ?
C9 C8 H8 108.5 . . ?
C8 C9 H9 108.9 . . ?
C8 C9 C10 110.95(12) . . ?
C10 C9 H9 108.9 . . ?
C13 C9 C8 114.39(12) . . ?
C13 C9 H9 108.9 . . ?
C13 C9 C10 104.69(12) . . ?
C9 C10 H10 108.9 . . ?
C9 C10 C11 117.43(12) . . ?
C11 C10 H10 108.9 . . ?
C14 C10 C9 104.35(12) . . ?
C14 C10 H10 108.9 . . ?
C14 C10 C11 107.92(12) . . ?
C10 C11 H11 107.2 . . ?
C12 C11 C10 109.86(12) . . ?
C12 C11 H11 107.2 . . ?
C12 C11 C15 112.90(12) . . ?
C15 C11 C10 112.06(12) . . ?
C15 C11 H11 107.2 . . ?
C7 C12 C11 118.95(13) . . ?
C7 C12 H12 120.5 . . ?
C11 C12 H12 120.5 . . ?
O1 C13 N2 124.66(15) . . ?
O1 C13 C9 127.44(14) . . ?
N2 C13 C9 107.84(13) . . ?
O2 C14 N2 125.03(15) . . ?
O2 C14 C10 126.37(14) . . ?
N2 C14 C10 108.60(13) . . ?
C11 C15 H15A 109.5 . . ?
C11 C15 H15B 109.5 . . ?
H15A C15 H15B 108.1 . . ?
C16 C15 C11 110.70(13) . . ?
C16 C15 H15A 109.5 . . ?
C16 C15 H15B 109.5 . . ?
C15 C16 H16A 108.8 . . ?
C15 C16 H16B 108.8 . . ?
H16A C16 H16B 107.7 . . ?
C17 C16 C15 113.99(15) . . ?
C17 C16 H16A 108.8 . . ?
C17 C16 H16B 108.8 . . ?
O3 C17 C16 124.21(17) . . ?
O3 C17 O4B 124.2(5) . . ?
O3 C17 O4A 121.9(4) . . ?
O3 C17 O4C 125.4(3) . . ?
O4B C17 C16 106.4(5) . . ?
O4A C17 C16 112.2(4) . . ?
O4C C17 C16 110.2(3) . . ?
C21 C20 S1 119.04(12) . . ?
C21 C20 C25 120.70(15) . . ?
C25 C20 S1 120.25(12) . . ?
C20 C21 H21 120.4 . . ?
C22 C21 C20 119.22(15) . . ?
C22 C21 H21 120.4 . . ?
C21 C22 H22 119.3 . . ?
C21 C22 C23 121.40(15) . . ?
C23 C22 H22 119.3 . . ?
C22 C23 C24 118.33(16) . . ?
C22 C23 C26 120.42(17) . . ?
C24 C23 C26 121.24(17) . . ?
C23 C24 H24 119.4 . . ?
C25 C24 C23 121.24(16) . . ?
C25 C24 H24 119.4 . . ?
C20 C25 H25 120.4 . . ?
C24 C25 C20 119.10(15) . . ?
C24 C25 H25 120.4 . . ?
C23 C26 H26A 109.5 . . ?
C23 C26 H26B 109.5 . . ?
C23 C26 H26C 109.5 . . ?
H26A C26 H26B 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
C17 O4B C18B 113.3(10) . . ?
O4B C18B H18A 110.3 . . ?
O4B C18B H18B 110.3 . . ?
O4B C18B C19B 107.3(12) . . ?
H18A C18B H18B 108.5 . . ?
C19B C18B H18A 110.3 . . ?
C19B C18B H18B 110.3 . . ?
C18B C19B H19A 109.5 . . ?
C18B C19B H19B 109.5 . . ?
C18B C19B H19C 109.5 . . ?
H19A C19B H19B 109.5 . . ?
H19A C19B H19C 109.5 . . ?
H19B C19B H19C 109.5 . . ?
C17 O4A C18A 119.0(6) . . ?
O4A C18A H18C 109.6 . . ?
O4A C18A H18D 109.6 . . ?
O4A C18A C19A 110.4(6) . . ?
H18C C18A H18D 108.1 . . ?
C19A C18A H18C 109.6 . . ?
C19A C18A H18D 109.6 . . ?
C18A C19A H19D 109.5 . . ?
C18A C19A H19E 109.5 . . ?
C18A C19A H19F 109.5 . . ?
H19D C19A H19E 109.5 . . ?
H19D C19A H19F 109.5 . . ?
H19E C19A H19F 109.5 . . ?
C17 O4C C18C 117.5(5) . . ?
O4C C18C H18E 110.0 . . ?
O4C C18C H18F 110.0 . . ?
O4C C18C C19C 108.5(6) . . ?
H18E C18C H18F 108.4 . . ?
C19C C18C H18E 110.0 . . ?
C19C C18C H18F 110.0 . . ?
C18C C19C H19G 109.5 . . ?
C18C C19C H19H 109.5 . . ?
C18C C19C H19I 109.5 . . ?
H19G C19C H19H 109.5 . . ?
H19G C19C H19I 109.5 . . ?
H19H C19C H19I 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
S1 N1 C1 C2 144.94(11) . . . . ?
S1 N1 C1 C6 -38.5(2) . . . . ?
S1 N1 C8 C7 -148.41(10) . . . . ?
S1 N1 C8 C9 89.76(13) . . . . ?
S1 C20 C21 C22 -179.27(12) . . . . ?
S1 C20 C25 C24 178.78(13) . . . . ?
O3 C17 O4B C18B -20.9(12) . . . . ?
O3 C17 O4A C18A 11.1(7) . . . . ?
O3 C17 O4C C18C -1.6(6) . . . . ?
O5 S1 N1 C1 44.67(13) . . . . ?
O5 S1 N1 C8 -178.47(10) . . . . ?
O5 S1 C20 C21 -24.54(14) . . . . ?
O5 S1 C20 C25 156.27(12) . . . . ?
O6 S1 N1 C1 173.69(11) . . . . ?
O6 S1 N1 C8 -49.44(12) . . . . ?
O6 S1 C20 C21 -155.94(12) . . . . ?
O6 S1 C20 C25 24.87(15) . . . . ?
N1 S1 C20 C21 90.53(13) . . . . ?
N1 S1 C20 C25 -88.66(14) . . . . ?
N1 C1 C2 C3 176.64(13) . . . . ?
N1 C1 C2 C7 -1.86(17) . . . . ?
N1 C1 C6 C5 -177.02(14) . . . . ?
N1 C8 C9 C10 165.10(12) . . . . ?
N1 C8 C9 C13 46.95(17) . . . . ?
C1 N1 C8 C7 -6.17(14) . . . . ?
C1 N1 C8 C9 -128.01(13) . . . . ?
C1 C2 C3 C4 1.0(2) . . . . ?
C1 C2 C7 C8 -2.14(16) . . . . ?
C1 C2 C7 C12 174.20(16) . . . . ?
C2 C1 C6 C5 -0.8(2) . . . . ?
C2 C3 C4 C5 -0.7(2) . . . . ?
C2 C7 C8 N1 5.03(15) . . . . ?
C2 C7 C8 C9 130.66(12) . . . . ?
C2 C7 C12 C11 -177.23(14) . . . . ?
C3 C2 C7 C8 179.55(15) . . . . ?
C3 C2 C7 C12 -4.1(3) . . . . ?
C3 C4 C5 C6 -0.3(3) . . . . ?
C4 C5 C6 C1 1.1(2) . . . . ?
C6 C1 C2 C3 -0.2(2) . . . . ?
C6 C1 C2 C7 -178.74(13) . . . . ?
C7 C2 C3 C4 179.11(15) . . . . ?
C7 C8 C9 C10 46.69(16) . . . . ?
C7 C8 C9 C13 -71.46(16) . . . . ?
C8 N1 C1 C2 5.19(16) . . . . ?
C8 N1 C1 C6 -178.22(14) . . . . ?
C8 C7 C12 C11 -1.3(2) . . . . ?
C8 C9 C10 C11 -6.72(17) . . . . ?
C8 C9 C10 C14 -126.11(13) . . . . ?
C8 C9 C13 O1 -59.2(2) . . . . ?
C8 C9 C13 N2 123.63(13) . . . . ?
C9 C10 C11 C12 -36.79(17) . . . . ?
C9 C10 C11 C15 89.57(15) . . . . ?
C9 C10 C14 O2 -178.76(15) . . . . ?
C9 C10 C14 N2 1.80(16) . . . . ?
C10 C9 C13 O1 179.12(15) . . . . ?
C10 C9 C13 N2 1.98(15) . . . . ?
C10 C11 C12 C7 42.64(18) . . . . ?
C10 C11 C15 C16 170.57(12) . . . . ?
C11 C10 C14 O2 55.62(19) . . . . ?
C11 C10 C14 N2 -123.82(13) . . . . ?
C11 C15 C16 C17 -179.09(14) . . . . ?
C12 C7 C8 N1 -171.82(13) . . . . ?
C12 C7 C8 C9 -46.20(18) . . . . ?
C12 C11 C15 C16 -64.74(17) . . . . ?
C13 N2 C14 O2 179.95(15) . . . . ?
C13 N2 C14 C10 -0.60(18) . . . . ?
C13 C9 C10 C11 117.16(13) . . . . ?
C13 C9 C10 C14 -2.23(14) . . . . ?
C14 N2 C13 O1 -178.16(15) . . . . ?
C14 N2 C13 C9 -0.92(18) . . . . ?
C14 C10 C11 C12 80.69(14) . . . . ?
C14 C10 C11 C15 -152.96(12) . . . . ?
C15 C11 C12 C7 -83.24(17) . . . . ?
C15 C16 C17 O3 128.4(2) . . . . ?
C15 C16 C17 O4B -76.2(5) . . . . ?
C15 C16 C17 O4A -36.8(4) . . . . ?
C15 C16 C17 O4C -56.4(3) . . . . ?
C16 C17 O4B C18B -176.3(8) . . . . ?
C16 C17 O4A C18A 176.7(5) . . . . ?
C16 C17 O4C C18C -176.7(4) . . . . ?
C17 O4B C18B C19B 102.9(14) . . . . ?
C17 O4A C18A C19A 82.2(8) . . . . ?
C17 O4C C18C C19C 90.7(7) . . . . ?
C20 S1 N1 C1 -71.35(13) . . . . ?
C20 S1 N1 C8 65.51(11) . . . . ?
C20 C21 C22 C23 0.6(3) . . . . ?
C21 C20 C25 C24 -0.4(2) . . . . ?
C21 C22 C23 C24 -0.7(3) . . . . ?
C21 C22 C23 C26 178.37(19) . . . . ?
C22 C23 C24 C25 0.2(3) . . . . ?
C23 C24 C25 C20 0.4(3) . . . . ?
C25 C20 C21 C22 -0.1(2) . . . . ?
C26 C23 C24 C25 -178.9(2) . . . . ?

loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
0 1 0 0.1146 0.0001 1.0001 0.0008 -0.1357 -0.0178 -0.1078
1 0 2 0.1131 0.9996 -0.0004 1.9995 -0.1414 0.0086 0.1765
-1 0 -2 0.1541 -0.9996 0.0004 -1.9995 0.1414 -0.0086 -0.1765
1 0 -1 0.0869 0.9998 -0.0002 -1.0007 0.0028 0.1113 -0.0219
-1 0 1 0.0489 -0.9998 0.0002 1.0007 -0.0028 -0.1113 0.0219
1 -1 2 0.1485 0.9996 -1.0005 1.9987 -0.0057 0.0264 0.2843
1 -3 -3 0.1224 0.9997 -3.0004 -3.0033 0.5060 0.2332 0.1694
-1 -1 -3 0.1260 -0.9997 -0.9996 -3.0004 0.3252 0.0435 -0.1348
2 -1 -1 0.1405 1.9994 -1.0005 -1.0021 0.0932 0.2062 0.1302

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_mjh140002
_database_code_depnum_ccdc_archive 'CCDC 1040307'
_audit_update_record             
;
2014-12-18 deposited with the CCDC.
2015-01-16 downloaded from the CCDC.
;
_audit_creation_date             2014-05-19
_audit_creation_method           
;
Olex2 1.2-alpha
(compiled 2014.03.20 svn.r2918 for OlexSys, GUI svn.r4816)
;
_shelxl_version_number           2013-4
_chemical_name_common            ?
_chemical_name_systematic        
6-(3,5-dioxo-4-phenyl-1,2,4-triazolidin-1-yl)-2-phenyl-11-tosyl-5,6-dihydro-[1,2,4]triazolo[1',2':1,2]pyridazino[3,4-b]indole-1,3(2H,11H)-dione
_chemical_formula_moiety         'C33 H25 N7 O6 S'
_chemical_formula_sum            'C33 H25 N7 O6 S'
_chemical_formula_weight         647.66
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C33 H25 N7 O6 S1'
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                   13.1236(3)
_cell_length_b                   20.8432(5)
_cell_length_c                   12.0391(2)
_cell_angle_alpha                90
_cell_angle_beta                 100.991(2)
_cell_angle_gamma                90
_cell_volume                     3232.74(13)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    7905
_cell_measurement_temperature    150.00(10)
_cell_measurement_theta_max      66.0850
_cell_measurement_theta_min      3.3860
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    1.360
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.92025
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.331
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             1344
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.06
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0383
_diffrn_reflns_av_unetI/netI     0.0297
_diffrn_reflns_Laue_measured_fraction_full 0.965
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            23327
_diffrn_reflns_point_group_measured_fraction_full 0.965
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         66.247
_diffrn_reflns_theta_min         3.431
_diffrn_ambient_temperature      150.00(10)
_diffrn_detector_area_resol_mean 10.3968
_diffrn_measured_fraction_theta_full 0.965
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini ultra'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0936454000
_diffrn_orient_matrix_UB_12      -0.0040772000
_diffrn_orient_matrix_UB_13      -0.0987299000
_diffrn_orient_matrix_UB_21      0.0358684000
_diffrn_orient_matrix_UB_22      0.0620523000
_diffrn_orient_matrix_UB_23      -0.0507830000
_diffrn_orient_matrix_UB_31      0.0650071000
_diffrn_orient_matrix_UB_32      -0.0400248000
_diffrn_orient_matrix_UB_33      -0.0683558000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Enhance Ultra (Cu) X-ray Source'
_diffrn_special_details          ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4665
_reflns_number_total             5646
_reflns_odcompleteness_completeness 98.81
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.49
_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 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XT (Sheldrick, 2008)'
_refine_diff_density_max         0.355
_refine_diff_density_min         -0.365
_refine_diff_density_rms         0.042
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     428
_refine_ls_number_reflns         5646
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0464
_refine_ls_R_factor_gt           0.0357
_refine_ls_restrained_S_all      1.036
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0445P)²+1.0584P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0863
_refine_ls_wR_factor_ref         0.0927
_refine_special_details          
;
Crystal contains large voids which are empty,
 the data have been used as integrated from
 the diffractometer.
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C8(H8)
2.b Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B)
2.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C16(H16), C17(H17), C18(H18), C19(H19),
 C20(H20), C22(H22), C23(H23), C24(H24), C25(H25), C26(H26), C28(H28), C29(H29),
  C31(H31), C32(H32)
2.d Idealised Me refined as rotating group:
 C33(H33A,H33B,H33C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_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 0.85569(3) 0.78263(2) 0.70846(3) 0.02268(11) Uani 1 1 d . . . . .
O1 O 0.47498(9) 0.78249(6) 0.25233(10) 0.0302(3) Uani 1 1 d . . . . .
O2 O 0.61621(10) 0.85176(6) 0.61044(10) 0.0288(3) Uani 1 1 d . . . . .
O3 O 0.43028(9) 0.56865(6) 0.31491(11) 0.0327(3) Uani 1 1 d . . . . .
O4 O 0.27947(10) 0.73404(6) 0.47585(10) 0.0330(3) Uani 1 1 d . . . . .
O5 O 0.83718(9) 0.82875(6) 0.61999(10) 0.0281(3) Uani 1 1 d . . . . .
O6 O 0.86731(9) 0.80218(6) 0.82377(10) 0.0283(3) Uani 1 1 d . . . . .
N1 N 0.75235(10) 0.73208(7) 0.68529(11) 0.0224(3) Uani 1 1 d . . . . .
N2 N 0.61018(11) 0.74616(7) 0.38907(11) 0.0229(3) Uani 1 1 d . . . . .
N3 N 0.53604(11) 0.83697(7) 0.42185(11) 0.0244(3) Uani 1 1 d . . . . .
N4 N 0.65898(11) 0.76875(7) 0.49809(11) 0.0222(3) Uani 1 1 d . . . . .
N5 N 0.48644(11) 0.63292(7) 0.47179(11) 0.0242(3) Uani 1 1 d . . . . .
N6 N 0.32644(11) 0.64713(7) 0.37465(12) 0.0255(3) Uani 1 1 d . . . . .
N7 N 0.44541(11) 0.69093(7) 0.50863(12) 0.0245(3) Uani 1 1 d . . . . .
H7 H 0.4564(15) 0.6956(10) 0.5792(19) 0.029 Uiso 1 1 d R . . . .
C1 C 0.76180(12) 0.67115(8) 0.74100(14) 0.0220(3) Uani 1 1 d . . . . .
C2 C 0.81099(13) 0.65557(9) 0.85001(14) 0.0259(4) Uani 1 1 d . . . . .
H2 H 0.8465 0.6870 0.9001 0.031 Uiso 1 1 calc R . . . .
C3 C 0.80608(14) 0.59203(9) 0.88266(15) 0.0291(4) Uani 1 1 d . . . . .
H3 H 0.8389 0.5798 0.9569 0.035 Uiso 1 1 calc R . . . .
C4 C 0.75448(14) 0.54557(9) 0.80989(15) 0.0296(4) Uani 1 1 d . . . . .
H4 H 0.7532 0.5024 0.8350 0.035 Uiso 1 1 calc R . . . .
C5 C 0.70484(14) 0.56163(9) 0.70108(15) 0.0275(4) Uani 1 1 d . . . . .
H5 H 0.6692 0.5301 0.6515 0.033 Uiso 1 1 calc R . . . .
C6 C 0.70865(12) 0.62515(8) 0.66651(14) 0.0231(4) Uani 1 1 d . . . . .
C7 C 0.66383(12) 0.65821(8) 0.56391(14) 0.0223(3) Uani 1 1 d . . . . .
C8 C 0.59607(12) 0.63512(8) 0.45776(14) 0.0234(4) Uani 1 1 d . . . . .
H8 H 0.6180 0.5905 0.4426 0.028 Uiso 1 1 calc R . . . .
C9 C 0.61530(14) 0.67853(8) 0.36024(14) 0.0248(4) Uani 1 1 d . . . . .
H9A H 0.6845 0.6689 0.3430 0.030 Uiso 1 1 calc R . . . .
H9B H 0.5626 0.6693 0.2916 0.030 Uiso 1 1 calc R . . . .
C10 C 0.53331(13) 0.78750(8) 0.34384(13) 0.0233(4) Uani 1 1 d . . . . .
C11 C 0.60450(13) 0.82337(8) 0.52207(14) 0.0233(4) Uani 1 1 d . . . . .
C12 C 0.69117(12) 0.72034(8) 0.57765(13) 0.0220(3) Uani 1 1 d . . . . .
C13 C 0.41549(13) 0.61075(8) 0.37897(14) 0.0244(4) Uani 1 1 d . . . . .
C14 C 0.34229(13) 0.69563(9) 0.45570(14) 0.0251(4) Uani 1 1 d . . . . .
C15 C 0.23677(13) 0.64079(9) 0.28575(14) 0.0264(4) Uani 1 1 d . . . . .
C16 C 0.15800(14) 0.59937(10) 0.29805(17) 0.0346(4) Uani 1 1 d . . . . .
H16 H 0.1609 0.5760 0.3663 0.041 Uiso 1 1 calc R . . . .
C17 C 0.07426(15) 0.59235(11) 0.20919(19) 0.0419(5) Uani 1 1 d . . . . .
H17 H 0.0189 0.5643 0.2167 0.050 Uiso 1 1 calc R . . . .
C18 C 0.07117(15) 0.62612(11) 0.10967(17) 0.0382(5) Uani 1 1 d . . . . .
H18 H 0.0144 0.6205 0.0484 0.046 Uiso 1 1 calc R . . . .
C19 C 0.14985(15) 0.66783(11) 0.09899(16) 0.0363(5) Uani 1 1 d . . . . .
H19 H 0.1467 0.6914 0.0309 0.044 Uiso 1 1 calc R . . . .
C20 C 0.23353(14) 0.67555(10) 0.18706(15) 0.0315(4) Uani 1 1 d . . . . .
H20 H 0.2881 0.7043 0.1800 0.038 Uiso 1 1 calc R . . . .
C21 C 0.46439(13) 0.89019(8) 0.41088(14) 0.0245(4) Uani 1 1 d . . . . .
C22 C 0.37956(14) 0.88680(9) 0.46378(15) 0.0300(4) Uani 1 1 d . . . . .
H22 H 0.3670 0.8493 0.5041 0.036 Uiso 1 1 calc R . . . .
C23 C 0.31362(15) 0.93880(10) 0.45687(16) 0.0342(4) Uani 1 1 d . . . . .
H23 H 0.2548 0.9369 0.4921 0.041 Uiso 1 1 calc R . . . .
C24 C 0.33233(15) 0.99375(9) 0.39910(16) 0.0338(4) Uani 1 1 d . . . . .
H24 H 0.2871 1.0296 0.3958 0.041 Uiso 1 1 calc R . . . .
C25 C 0.41709(15) 0.99618(9) 0.34632(16) 0.0346(4) Uani 1 1 d . . . . .
H25 H 0.4298 1.0337 0.3061 0.042 Uiso 1 1 calc R . . . .
C26 C 0.48324(14) 0.94435(9) 0.35184(15) 0.0302(4) Uani 1 1 d . . . . .
H26 H 0.5413 0.9459 0.3153 0.036 Uiso 1 1 calc R . . . .
C27 C 0.96011(13) 0.73286(9) 0.69364(14) 0.0252(4) Uani 1 1 d . . . . .
C28 C 1.04207(14) 0.72412(9) 0.78362(15) 0.0293(4) Uani 1 1 d . . . . .
H28 H 1.0416 0.7440 0.8545 0.035 Uiso 1 1 calc R . . . .
C29 C 1.12453(14) 0.68596(10) 0.76856(15) 0.0333(4) Uani 1 1 d . . . . .
H29 H 1.1812 0.6801 0.8297 0.040 Uiso 1 1 calc R . . . .
C30 C 1.12617(15) 0.65598(10) 0.66543(16) 0.0329(4) Uani 1 1 d . . . . .
C31 C 1.04264(15) 0.66586(10) 0.57666(16) 0.0355(4) Uani 1 1 d . . . . .
H31 H 1.0426 0.6458 0.5058 0.043 Uiso 1 1 calc R . . . .
C32 C 0.95990(14) 0.70411(9) 0.58952(15) 0.0305(4) Uani 1 1 d . . . . .
H32 H 0.9036 0.7107 0.5281 0.037 Uiso 1 1 calc R . . . .
C33 C 1.21717(17) 0.61467(12) 0.65172(19) 0.0475(6) Uani 1 1 d . . . . .
H33A H 1.2128 0.5734 0.6894 0.071 Uiso 1 1 calc GR . . . .
H33B H 1.2819 0.6363 0.6858 0.071 Uiso 1 1 calc GR . . . .
H33C H 1.2160 0.6075 0.5710 0.071 Uiso 1 1 calc GR . . . .


_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 O5 1.4209(12) . ?
S1 O6 1.4268(12) . ?
S1 N1 1.6979(14) . ?
S1 C27 1.7548(18) . ?
O1 C10 1.220(2) . ?
O2 C11 1.201(2) . ?
O3 C13 1.208(2) . ?
O4 C14 1.206(2) . ?
N1 C1 1.431(2) . ?
N1 C12 1.410(2) . ?
N2 N4 1.4263(19) . ?
N2 C9 1.456(2) . ?
N2 C10 1.359(2) . ?
N3 C10 1.391(2) . ?
N3 C11 1.389(2) . ?
N3 C21 1.444(2) . ?
N4 C11 1.403(2) . ?
N4 C12 1.400(2) . ?
N5 N7 1.428(2) . ?
N5 C8 1.481(2) . ?
N5 C13 1.390(2) . ?
N6 C13 1.386(2) . ?
N6 C14 1.393(2) . ?
N6 C15 1.438(2) . ?
N7 H7 0.84(2) . ?
N7 C14 1.385(2) . ?
C1 C2 1.386(2) . ?
C1 C6 1.404(2) . ?
C2 H2 0.9500 . ?
C2 C3 1.387(3) . ?
C3 H3 0.9500 . ?
C3 C4 1.392(3) . ?
C4 H4 0.9500 . ?
C4 C5 1.388(3) . ?
C5 H5 0.9500 . ?
C5 C6 1.392(3) . ?
C6 C7 1.439(2) . ?
C7 C8 1.491(2) . ?
C7 C12 1.346(2) . ?
C8 H8 1.0000 . ?
C8 C9 1.541(2) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C15 C16 1.376(3) . ?
C15 C20 1.385(3) . ?
C16 H16 0.9500 . ?
C16 C17 1.388(3) . ?
C17 H17 0.9500 . ?
C17 C18 1.384(3) . ?
C18 H18 0.9500 . ?
C18 C19 1.374(3) . ?
C19 H19 0.9500 . ?
C19 C20 1.383(3) . ?
C20 H20 0.9500 . ?
C21 C22 1.386(3) . ?
C21 C26 1.381(3) . ?
C22 H22 0.9500 . ?
C22 C23 1.379(3) . ?
C23 H23 0.9500 . ?
C23 C24 1.386(3) . ?
C24 H24 0.9500 . ?
C24 C25 1.383(3) . ?
C25 H25 0.9500 . ?
C25 C26 1.380(3) . ?
C26 H26 0.9500 . ?
C27 C28 1.385(2) . ?
C27 C32 1.389(2) . ?
C28 H28 0.9500 . ?
C28 C29 1.383(3) . ?
C29 H29 0.9500 . ?
C29 C30 1.394(3) . ?
C30 C31 1.393(3) . ?
C30 C33 1.507(3) . ?
C31 H31 0.9500 . ?
C31 C32 1.379(3) . ?
C32 H32 0.9500 . ?
C33 H33A 0.9800 . ?
C33 H33B 0.9800 . ?
C33 H33C 0.9800 . ?

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
O5 S1 O6 120.49(8) . . ?
O5 S1 N1 106.24(7) . . ?
O5 S1 C27 110.43(8) . . ?
O6 S1 N1 105.72(7) . . ?
O6 S1 C27 109.09(8) . . ?
N1 S1 C27 103.37(8) . . ?
C1 N1 S1 118.60(11) . . ?
C12 N1 S1 123.77(11) . . ?
C12 N1 C1 105.08(13) . . ?
N4 N2 C9 120.39(13) . . ?
C10 N2 N4 109.16(13) . . ?
C10 N2 C9 125.64(14) . . ?
C10 N3 C21 125.13(14) . . ?
C11 N3 C10 111.37(14) . . ?
C11 N3 C21 122.57(14) . . ?
C11 N4 N2 107.47(12) . . ?
C12 N4 N2 114.57(13) . . ?
C12 N4 C11 122.90(13) . . ?
N7 N5 C8 116.18(13) . . ?
C13 N5 N7 107.26(13) . . ?
C13 N5 C8 115.79(13) . . ?
C13 N6 C14 111.02(14) . . ?
C13 N6 C15 122.84(14) . . ?
C14 N6 C15 125.44(15) . . ?
N5 N7 H7 114.2(14) . . ?
C14 N7 N5 108.07(13) . . ?
C14 N7 H7 114.9(14) . . ?
C2 C1 N1 129.42(15) . . ?
C2 C1 C6 121.99(16) . . ?
C6 C1 N1 108.58(14) . . ?
C1 C2 H2 121.5 . . ?
C1 C2 C3 116.98(16) . . ?
C3 C2 H2 121.5 . . ?
C2 C3 H3 119.0 . . ?
C2 C3 C4 121.97(16) . . ?
C4 C3 H3 119.0 . . ?
C3 C4 H4 119.6 . . ?
C5 C4 C3 120.70(17) . . ?
C5 C4 H4 119.6 . . ?
C4 C5 H5 120.8 . . ?
C4 C5 C6 118.33(17) . . ?
C6 C5 H5 120.8 . . ?
C1 C6 C7 107.06(15) . . ?
C5 C6 C1 120.03(15) . . ?
C5 C6 C7 132.87(16) . . ?
C6 C7 C8 131.37(16) . . ?
C12 C7 C6 107.43(15) . . ?
C12 C7 C8 121.17(15) . . ?
N5 C8 C7 110.24(13) . . ?
N5 C8 H8 108.2 . . ?
N5 C8 C9 114.14(14) . . ?
C7 C8 H8 108.2 . . ?
C7 C8 C9 107.82(14) . . ?
C9 C8 H8 108.2 . . ?
N2 C9 C8 111.41(13) . . ?
N2 C9 H9A 109.3 . . ?
N2 C9 H9B 109.3 . . ?
C8 C9 H9A 109.3 . . ?
C8 C9 H9B 109.3 . . ?
H9A C9 H9B 108.0 . . ?
O1 C10 N2 126.68(16) . . ?
O1 C10 N3 127.17(16) . . ?
N2 C10 N3 106.14(13) . . ?
O2 C11 N3 128.38(16) . . ?
O2 C11 N4 126.70(15) . . ?
N3 C11 N4 104.92(13) . . ?
N4 C12 N1 123.27(15) . . ?
C7 C12 N1 111.83(14) . . ?
C7 C12 N4 124.82(15) . . ?
O3 C13 N5 126.16(16) . . ?
O3 C13 N6 127.62(16) . . ?
N6 C13 N5 106.21(14) . . ?
O4 C14 N6 127.30(16) . . ?
O4 C14 N7 126.84(16) . . ?
N7 C14 N6 105.86(15) . . ?
C16 C15 N6 120.17(16) . . ?
C16 C15 C20 121.29(17) . . ?
C20 C15 N6 118.50(16) . . ?
C15 C16 H16 120.5 . . ?
C15 C16 C17 118.95(19) . . ?
C17 C16 H16 120.5 . . ?
C16 C17 H17 119.9 . . ?
C18 C17 C16 120.13(19) . . ?
C18 C17 H17 119.9 . . ?
C17 C18 H18 119.9 . . ?
C19 C18 C17 120.29(18) . . ?
C19 C18 H18 119.9 . . ?
C18 C19 H19 119.9 . . ?
C18 C19 C20 120.19(19) . . ?
C20 C19 H19 119.9 . . ?
C15 C20 H20 120.4 . . ?
C19 C20 C15 119.13(18) . . ?
C19 C20 H20 120.4 . . ?
C22 C21 N3 119.02(16) . . ?
C26 C21 N3 119.84(15) . . ?
C26 C21 C22 121.10(17) . . ?
C21 C22 H22 120.6 . . ?
C23 C22 C21 118.81(17) . . ?
C23 C22 H22 120.6 . . ?
C22 C23 H23 119.7 . . ?
C22 C23 C24 120.69(17) . . ?
C24 C23 H23 119.7 . . ?
C23 C24 H24 120.1 . . ?
C25 C24 C23 119.72(18) . . ?
C25 C24 H24 120.1 . . ?
C24 C25 H25 119.9 . . ?
C26 C25 C24 120.20(18) . . ?
C26 C25 H25 119.9 . . ?
C21 C26 H26 120.3 . . ?
C25 C26 C21 119.47(17) . . ?
C25 C26 H26 120.3 . . ?
C28 C27 S1 120.22(14) . . ?
C28 C27 C32 121.11(17) . . ?
C32 C27 S1 118.66(13) . . ?
C27 C28 H28 120.5 . . ?
C29 C28 C27 118.92(17) . . ?
C29 C28 H28 120.5 . . ?
C28 C29 H29 119.3 . . ?
C28 C29 C30 121.34(17) . . ?
C30 C29 H29 119.3 . . ?
C29 C30 C33 120.06(18) . . ?
C31 C30 C29 118.28(17) . . ?
C31 C30 C33 121.66(18) . . ?
C30 C31 H31 119.3 . . ?
C32 C31 C30 121.38(17) . . ?
C32 C31 H31 119.3 . . ?
C27 C32 H32 120.5 . . ?
C31 C32 C27 118.98(17) . . ?
C31 C32 H32 120.5 . . ?
C30 C33 H33A 109.5 . . ?
C30 C33 H33B 109.5 . . ?
C30 C33 H33C 109.5 . . ?
H33A C33 H33B 109.5 . . ?
H33A C33 H33C 109.5 . . ?
H33B C33 H33C 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
S1 N1 C1 C2 39.0(2) . . . . ?
S1 N1 C1 C6 -142.48(12) . . . . ?
S1 N1 C12 N4 -42.5(2) . . . . ?
S1 N1 C12 C7 140.63(13) . . . . ?
S1 C27 C28 C29 -178.34(15) . . . . ?
S1 C27 C32 C31 178.84(15) . . . . ?
O5 S1 N1 C1 162.84(12) . . . . ?
O5 S1 N1 C12 26.69(15) . . . . ?
O5 S1 C27 C28 127.75(15) . . . . ?
O5 S1 C27 C32 -50.54(16) . . . . ?
O6 S1 N1 C1 -68.04(13) . . . . ?
O6 S1 N1 C12 155.81(13) . . . . ?
O6 S1 C27 C28 -6.82(17) . . . . ?
O6 S1 C27 C32 174.89(14) . . . . ?
N1 S1 C27 C28 -118.97(15) . . . . ?
N1 S1 C27 C32 62.74(16) . . . . ?
N1 C1 C2 C3 178.76(16) . . . . ?
N1 C1 C6 C5 -179.13(14) . . . . ?
N1 C1 C6 C7 -1.14(18) . . . . ?
N2 N4 C11 O2 172.01(16) . . . . ?
N2 N4 C11 N3 -8.45(17) . . . . ?
N2 N4 C12 N1 171.67(13) . . . . ?
N2 N4 C12 C7 -11.9(2) . . . . ?
N3 C21 C22 C23 177.42(16) . . . . ?
N3 C21 C26 C25 -176.93(16) . . . . ?
N4 N2 C9 C8 43.55(19) . . . . ?
N4 N2 C10 O1 -178.97(16) . . . . ?
N4 N2 C10 N3 2.10(17) . . . . ?
N5 N7 C14 O4 170.66(17) . . . . ?
N5 N7 C14 N6 -9.46(17) . . . . ?
N5 C8 C9 N2 73.84(18) . . . . ?
N6 C15 C16 C17 -177.53(17) . . . . ?
N6 C15 C20 C19 177.24(17) . . . . ?
N7 N5 C8 C7 54.12(18) . . . . ?
N7 N5 C8 C9 -67.40(18) . . . . ?
N7 N5 C13 O3 167.98(16) . . . . ?
N7 N5 C13 N6 -11.18(17) . . . . ?
C1 N1 C12 N4 176.54(14) . . . . ?
C1 N1 C12 C7 -0.32(18) . . . . ?
C1 C2 C3 C4 0.1(3) . . . . ?
C1 C6 C7 C8 -177.21(16) . . . . ?
C1 C6 C7 C12 0.94(18) . . . . ?
C2 C1 C6 C5 -0.4(2) . . . . ?
C2 C1 C6 C7 177.55(15) . . . . ?
C2 C3 C4 C5 -0.5(3) . . . . ?
C3 C4 C5 C6 0.5(3) . . . . ?
C4 C5 C6 C1 0.0(2) . . . . ?
C4 C5 C6 C7 -177.36(17) . . . . ?
C5 C6 C7 C8 0.4(3) . . . . ?
C5 C6 C7 C12 178.57(18) . . . . ?
C6 C1 C2 C3 0.4(2) . . . . ?
C6 C7 C8 N5 82.3(2) . . . . ?
C6 C7 C8 C9 -152.50(17) . . . . ?
C6 C7 C12 N1 -0.38(19) . . . . ?
C6 C7 C12 N4 -177.18(15) . . . . ?
C7 C8 C9 N2 -49.01(18) . . . . ?
C8 N5 N7 C14 144.40(14) . . . . ?
C8 N5 C13 O3 36.4(2) . . . . ?
C8 N5 C13 N6 -142.72(14) . . . . ?
C8 C7 C12 N1 178.00(14) . . . . ?
C8 C7 C12 N4 1.2(3) . . . . ?
C9 N2 N4 C11 -152.66(14) . . . . ?
C9 N2 N4 C12 -12.3(2) . . . . ?
C9 N2 C10 O1 -23.8(3) . . . . ?
C9 N2 C10 N3 157.32(14) . . . . ?
C10 N2 N4 C11 4.08(17) . . . . ?
C10 N2 N4 C12 144.42(14) . . . . ?
C10 N2 C9 C8 -109.13(17) . . . . ?
C10 N3 C11 O2 -170.30(17) . . . . ?
C10 N3 C11 N4 10.17(18) . . . . ?
C10 N3 C21 C22 95.9(2) . . . . ?
C10 N3 C21 C26 -86.5(2) . . . . ?
C11 N3 C10 O1 173.30(16) . . . . ?
C11 N3 C10 N2 -7.78(18) . . . . ?
C11 N3 C21 C22 -72.0(2) . . . . ?
C11 N3 C21 C26 105.58(19) . . . . ?
C11 N4 C12 N1 -54.8(2) . . . . ?
C11 N4 C12 C7 121.65(19) . . . . ?
C12 N1 C1 C2 -177.65(17) . . . . ?
C12 N1 C1 C6 0.91(17) . . . . ?
C12 N4 C11 O2 35.7(3) . . . . ?
C12 N4 C11 N3 -144.72(15) . . . . ?
C12 C7 C8 N5 -95.63(18) . . . . ?
C12 C7 C8 C9 29.6(2) . . . . ?
C13 N5 N7 C14 13.08(17) . . . . ?
C13 N5 C8 C7 -178.68(14) . . . . ?
C13 N5 C8 C9 59.80(19) . . . . ?
C13 N6 C14 O4 -177.59(17) . . . . ?
C13 N6 C14 N7 2.53(18) . . . . ?
C13 N6 C15 C16 92.0(2) . . . . ?
C13 N6 C15 C20 -85.9(2) . . . . ?
C14 N6 C13 O3 -173.61(17) . . . . ?
C14 N6 C13 N5 5.55(18) . . . . ?
C14 N6 C15 C16 -98.4(2) . . . . ?
C14 N6 C15 C20 83.6(2) . . . . ?
C15 N6 C13 O3 -2.7(3) . . . . ?
C15 N6 C13 N5 176.42(15) . . . . ?
C15 N6 C14 O4 11.8(3) . . . . ?
C15 N6 C14 N7 -168.06(15) . . . . ?
C15 C16 C17 C18 0.7(3) . . . . ?
C16 C15 C20 C19 -0.7(3) . . . . ?
C16 C17 C18 C19 -1.4(3) . . . . ?
C17 C18 C19 C20 1.0(3) . . . . ?
C18 C19 C20 C15 0.0(3) . . . . ?
C20 C15 C16 C17 0.3(3) . . . . ?
C21 N3 C10 O1 4.2(3) . . . . ?
C21 N3 C10 N2 -176.90(15) . . . . ?
C21 N3 C11 O2 -0.9(3) . . . . ?
C21 N3 C11 N4 179.61(14) . . . . ?
C21 C22 C23 C24 -0.7(3) . . . . ?
C22 C21 C26 C25 0.6(3) . . . . ?
C22 C23 C24 C25 1.0(3) . . . . ?
C23 C24 C25 C26 -0.5(3) . . . . ?
C24 C25 C26 C21 -0.3(3) . . . . ?
C26 C21 C22 C23 -0.2(3) . . . . ?
C27 S1 N1 C1 46.55(13) . . . . ?
C27 S1 N1 C12 -89.60(14) . . . . ?
C27 C28 C29 C30 -0.5(3) . . . . ?
C28 C27 C32 C31 0.6(3) . . . . ?
C28 C29 C30 C31 0.6(3) . . . . ?
C28 C29 C30 C33 -179.98(19) . . . . ?
C29 C30 C31 C32 -0.1(3) . . . . ?
C30 C31 C32 C27 -0.4(3) . . . . ?
C32 C27 C28 C29 -0.1(3) . . . . ?
C33 C30 C31 C32 -179.5(2) . . . . ?

_vrf_PLAT601_mjh140002           
;
PROBLEM: Structure Contains Solvent Accessible VOIDS of .
RESPONSE: Please see refine special details - in short there are 
voids present which are indeed empty
;
####################################################################### 
# 
# 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_mjh69
_database_code_depnum_ccdc_archive 'CCDC 1040308'
_audit_update_record             
;
2014-12-18 deposited with the CCDC.
2015-01-16 downloaded from the CCDC.
;
_audit_creation_date             2014-12-17
_audit_creation_method           
;
Olex2 1.2-alpha
(compiled 2014.12.09 svn.r3114 for OlexSys, GUI svn.r4963)
;
_shelxl_version_number           2014/6
_chemical_name_common            ?
_chemical_name_systematic        
(3aS*,5S*,10bS*)-5-((2,6-dibromophenyl)(hydroxy)amino)-N,N-dimethyl-1,3-dioxo-2-phenyl-1,3,3a,4,5,10b-hexahydropyrrolo[3,4-a]carbazole-10(2H)-sulfonamide
_chemical_formula_moiety         'C28 H24 Br2 N4 O5 S, C4 H10 O'
_chemical_formula_sum            'C32 H34 Br2 N4 O6 S'
_chemical_formula_weight         762.51
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C32 H34 O6 S1 Br2 N4'
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'
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'
Br Br -0.2901 2.4595 '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'

_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                   10.0627(11)
_cell_length_b                   12.5064(17)
_cell_length_c                   13.7858(16)
_cell_angle_alpha                87.321(10)
_cell_angle_beta                 78.605(10)
_cell_angle_gamma                70.030(11)
_cell_volume                     1598.0(4)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    3099
_cell_measurement_temperature    150.00(10)
_cell_measurement_theta_max      26.7130
_cell_measurement_theta_min      2.9480
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    2.653
_exptl_absorpt_correction_T_max  0.698
_exptl_absorpt_correction_T_min  0.300
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
Analytical numeric absorption correction using a multifaceted crystal
			model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.585
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             776
_exptl_crystal_size_max          0.7113
_exptl_crystal_size_mid          0.156
_exptl_crystal_size_min          0.1482
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0263
_diffrn_reflns_av_unetI/netI     0.0504
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.887
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            10012
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.887
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.798
_diffrn_reflns_theta_min         2.894
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      150.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.3968
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.887
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -67.00  -37.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      -23.7292   77.0000  -60.0000 30

#__ type_ start__ end____ width___ exp.time_
  2 omega  -92.00  -42.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      -23.7292  179.0000   90.0000 50

#__ type_ start__ end____ width___ exp.time_
  3 omega -118.00  -42.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      -23.7292  179.0000 -150.0000 76

#__ type_ start__ end____ width___ exp.time_
  4 omega -104.00   78.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      -23.7292   38.0000  150.0000 182

#__ type_ start__ end____ width___ exp.time_
  5 omega   92.00  130.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       25.1354  159.0000 -143.0000 38

#__ type_ start__ end____ width___ exp.time_
  6 omega  -61.00   25.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       25.1354  -38.0000 -120.0000 86
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini ultra'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0419430000
_diffrn_orient_matrix_UB_12      0.0087615000
_diffrn_orient_matrix_UB_13      0.0486336000
_diffrn_orient_matrix_UB_21      -0.0598782000
_diffrn_orient_matrix_UB_22      0.0373809000
_diffrn_orient_matrix_UB_23      -0.0184265000
_diffrn_orient_matrix_UB_31      -0.0223313000
_diffrn_orient_matrix_UB_32      -0.0465732000
_diffrn_orient_matrix_UB_33      -0.0071723000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4915
_reflns_number_total             6056
_reflns_odcompleteness_completeness 92.08
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XT (Sheldrick, 2008)'
_refine_diff_density_max         3.753
_refine_diff_density_min         -0.917
_refine_diff_density_rms         0.122
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     414
_refine_ls_number_reflns         6056
_refine_ls_number_restraints     366
_refine_ls_R_factor_all          0.0755
_refine_ls_R_factor_gt           0.0604
_refine_ls_restrained_S_all      1.015
_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)+(0.0662P)²+7.5386P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1457
_refine_ls_wR_factor_ref         0.1595
_refine_special_details          
;
There is still some residual density unmodelled in
 the final structure. The distance between the
 largest of these peaks is such that they
 correspond to a 5 percent contamination of the
 diffraction pattern by a satallite crystal. The
 integration software is not capable of resolving
 this and attempts to model as a twin with hklf5
 refinements are not successful. The satellite
 crystal is very minor compared to the major
 component and does not affect the stability of the
 main component refinement. It is only due the the
 electron count in Br atoms that allows the
 presence of this parasitic diffraction to be
 observed in the refinement.
;
_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. Rigid body (RIGU) restrains
 All non-hydrogen atoms
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
3.a Ternary CH refined with riding coordinates:
 C13(H13), C4(H4), C2(H2)
3.b Secondary CH2 refined with riding coordinates:
 C3(H3A,H3B), C31(H31A,H31B), C30(H30A,H30B)
3.c Aromatic/amide H refined with riding coordinates:
 C7(H7), C10(H10), C9(H9), C20(H20), C8(H8), C23(H23), C25(H25), C16(H16),
 C18(H18), C19(H19), C24(H24), C17(H17)
3.d Idealised Me refined as rotating group:
 C27(H27A,H27B,H27C), C28(H28A,H28B,H28C), C32(H32A,H32B,H32C), C29(H29A,H29B,
 H29C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_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
Br2 Br 0.65589(6) 0.64258(5) 0.62509(4) 0.03544(18) Uani 1 1 d . U . . .
Br1 Br 0.41111(7) 0.81678(5) 1.02336(4) 0.03548(18) Uani 1 1 d . U . . .
S1 S 0.23440(13) 0.72006(11) 0.53191(9) 0.0230(3) Uani 1 1 d . U . . .
O5 O 0.5876(4) 0.5882(3) 0.9307(3) 0.0241(8) Uani 1 1 d . U . . .
O3 O 0.3301(4) 0.6147(3) 0.4873(3) 0.0297(8) Uani 1 1 d . U . . .
O2 O 0.2054(4) 0.4441(3) 0.6219(3) 0.0286(8) Uani 1 1 d . U . . .
O1 O 0.5957(4) 0.2341(3) 0.7513(3) 0.0311(9) Uani 1 1 d . U . . .
O4 O 0.2803(5) 0.8166(3) 0.5207(3) 0.0372(9) Uani 1 1 d . U . . .
O6 O 0.8793(4) 0.4988(4) 0.8772(3) 0.0410(10) Uani 1 1 d . U . . .
N2 N 0.1937(4) 0.6947(3) 0.6534(3) 0.0201(8) Uani 1 1 d . U . . .
N4 N 0.5300(4) 0.6253(3) 0.8423(3) 0.0216(9) Uani 1 1 d . U . . .
N1 N 0.3923(5) 0.3167(3) 0.6842(3) 0.0247(9) Uani 1 1 d . U . . .
N3 N 0.0779(5) 0.7559(4) 0.5025(3) 0.0299(10) Uani 1 1 d . U . . .
C5 C 0.2966(5) 0.6668(4) 0.7893(4) 0.0202(9) Uani 1 1 d . U . . .
C13 C 0.3973(5) 0.5032(4) 0.6653(4) 0.0208(10) Uani 1 1 d . U . . .
H13 H 0.4600 0.5081 0.6004 0.025 Uiso 1 1 calc R . . . .
C12 C 0.3026(5) 0.6207(4) 0.7014(4) 0.0194(9) Uani 1 1 d . U . . .
C4 C 0.3884(5) 0.6054(4) 0.8616(4) 0.0201(10) Uani 1 1 d . U . . .
H4 H 0.3363 0.6295 0.9309 0.024 Uiso 1 1 calc R . . . .
C21 C 0.5329(5) 0.7382(4) 0.8207(4) 0.0236(10) Uani 1 1 d . U . . .
C11 C 0.1155(5) 0.7897(4) 0.7187(4) 0.0214(10) Uani 1 1 d . U . . .
C14 C 0.3149(5) 0.4236(4) 0.6532(4) 0.0221(10) Uani 1 1 d . U . . .
C6 C 0.1775(5) 0.7737(4) 0.8028(4) 0.0212(10) Uani 1 1 d . U . . .
C3 C 0.4243(6) 0.4776(4) 0.8467(4) 0.0232(10) Uani 1 1 d . U . . .
H3A H 0.3350 0.4586 0.8657 0.028 Uiso 1 1 calc R . . . .
H3B H 0.4912 0.4357 0.8904 0.028 Uiso 1 1 calc R . . . .
C1 C 0.5075(6) 0.3180(4) 0.7257(4) 0.0248(10) Uani 1 1 d . U . . .
C7 C 0.1137(6) 0.8522(4) 0.8818(4) 0.0267(11) Uani 1 1 d . U . . .
H7 H 0.1529 0.8428 0.9402 0.032 Uiso 1 1 calc R . . . .
C26 C 0.5950(6) 0.7581(5) 0.7244(4) 0.0279(11) Uani 1 1 d . U . . .
C15 C 0.3506(5) 0.2186(4) 0.6822(4) 0.0242(10) Uani 1 1 d . U . . .
C22 C 0.4936(6) 0.8280(5) 0.8892(4) 0.0286(11) Uani 1 1 d . U . . .
C10 C -0.0059(6) 0.8809(4) 0.7091(4) 0.0266(11) Uani 1 1 d . U . . .
H10 H -0.0464 0.8901 0.6513 0.032 Uiso 1 1 calc R . . . .
C2 C 0.4934(5) 0.4399(4) 0.7390(4) 0.0220(10) Uani 1 1 d . U . . .
H2 H 0.5901 0.4492 0.7213 0.026 Uiso 1 1 calc R . . . .
C9 C -0.0661(6) 0.9583(5) 0.7883(4) 0.0319(12) Uani 1 1 d . U . . .
H9 H -0.1490 1.0227 0.7843 0.038 Uiso 1 1 calc R . . . .
C20 C 0.3817(6) 0.1556(4) 0.5962(4) 0.0305(12) Uani 1 1 d . U . . .
H20 H 0.4325 0.1764 0.5369 0.037 Uiso 1 1 calc R . . . .
C8 C -0.0073(6) 0.9434(5) 0.8730(4) 0.0290(11) Uani 1 1 d . U . . .
H8 H -0.0516 0.9974 0.9261 0.035 Uiso 1 1 calc R . . . .
C23 C 0.5180(7) 0.9300(5) 0.8630(5) 0.0377(13) Uani 1 1 d . U . . .
H23 H 0.4911 0.9893 0.9112 0.045 Uiso 1 1 calc R . . . .
C25 C 0.6185(6) 0.8601(5) 0.6981(5) 0.0358(13) Uani 1 1 d . U . . .
H25 H 0.6605 0.8708 0.6320 0.043 Uiso 1 1 calc R . . . .
C16 C 0.2777(6) 0.1880(5) 0.7686(5) 0.0358(13) Uani 1 1 d . U . . .
H16 H 0.2566 0.2316 0.8278 0.043 Uiso 1 1 calc R . . . .
C18 C 0.2639(6) 0.0317(5) 0.6833(5) 0.0368(13) Uani 1 1 d . U . . .
H18 H 0.2328 -0.0320 0.6833 0.044 Uiso 1 1 calc R . . . .
C19 C 0.3382(6) 0.0616(5) 0.5968(5) 0.0352(13) Uani 1 1 d . U . . .
H19 H 0.3593 0.0176 0.5378 0.042 Uiso 1 1 calc R . . . .
C24 C 0.5807(7) 0.9447(5) 0.7680(5) 0.0387(13) Uani 1 1 d . U . . .
H24 H 0.5979 1.0139 0.7507 0.046 Uiso 1 1 calc R . . . .
C27 C 0.0208(7) 0.6635(6) 0.4971(5) 0.0471(16) Uani 1 1 d . U . . .
H27A H 0.0685 0.6195 0.4354 0.071 Uiso 1 1 calc GR . . . .
H27B H -0.0832 0.6957 0.4989 0.071 Uiso 1 1 calc GR . . . .
H27C H 0.0388 0.6136 0.5535 0.071 Uiso 1 1 calc GR . . . .
C17 C 0.2355(7) 0.0937(5) 0.7687(5) 0.0408(14) Uani 1 1 d . U . . .
H17 H 0.1865 0.0719 0.8282 0.049 Uiso 1 1 calc R . . . .
C31 C 0.9231(8) 0.4129(6) 0.8013(6) 0.0568(18) Uani 1 1 d . U . . .
H31A H 1.0292 0.3861 0.7799 0.068 Uiso 1 1 calc R . . . .
H31B H 0.8793 0.4446 0.7433 0.068 Uiso 1 1 calc R . . . .
C28 C 0.0525(8) 0.8430(7) 0.4258(6) 0.060(2) Uani 1 1 d . U . . .
H28A H 0.0824 0.9057 0.4421 0.090 Uiso 1 1 calc GR . . . .
H28B H -0.0503 0.8720 0.4230 0.090 Uiso 1 1 calc GR . . . .
H28C H 0.1085 0.8090 0.3614 0.090 Uiso 1 1 calc GR . . . .
C30 C 0.9273(8) 0.5929(7) 0.8511(7) 0.061(2) Uani 1 1 d . U . . .
H30A H 0.8840 0.6336 0.7955 0.074 Uiso 1 1 calc R . . . .
H30B H 1.0334 0.5658 0.8298 0.074 Uiso 1 1 calc R . . . .
C32 C 0.8756(8) 0.3168(6) 0.8407(6) 0.0554(18) Uani 1 1 d . U . . .
H32A H 0.9086 0.2560 0.7901 0.083 Uiso 1 1 calc GR . . . .
H32B H 0.7701 0.3432 0.8587 0.083 Uiso 1 1 calc GR . . . .
H32C H 0.9165 0.2877 0.8995 0.083 Uiso 1 1 calc GR . . . .
C29 C 0.8831(9) 0.6708(7) 0.9388(7) 0.068(2) Uani 1 1 d . U . . .
H29A H 0.9071 0.7396 0.9201 0.102 Uiso 1 1 calc GR . . . .
H29B H 0.9342 0.6325 0.9911 0.102 Uiso 1 1 calc GR . . . .
H29C H 0.7790 0.6917 0.9630 0.102 Uiso 1 1 calc GR . . . .
H5 H 0.672(7) 0.555(5) 0.910(5) 0.027(16) 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
Br2 C26 1.893(6) . ?
Br1 C22 1.892(6) . ?
S1 O3 1.420(4) . ?
S1 O4 1.424(4) . ?
S1 N2 1.685(4) . ?
S1 N3 1.612(4) . ?
O5 N4 1.442(5) . ?
O5 H5 0.81(6) . ?
O2 C14 1.204(6) . ?
O1 C1 1.211(6) . ?
O6 C31 1.429(8) . ?
O6 C30 1.424(8) . ?
N2 C12 1.426(6) . ?
N2 C11 1.423(6) . ?
N4 C4 1.500(6) . ?
N4 C21 1.437(6) . ?
N1 C14 1.395(6) . ?
N1 C1 1.395(6) . ?
N1 C15 1.428(6) . ?
N3 C27 1.466(8) . ?
N3 C28 1.476(8) . ?
C5 C12 1.348(7) . ?
C5 C4 1.499(7) . ?
C5 C6 1.449(7) . ?
C13 H13 1.0000 . ?
C13 C12 1.497(7) . ?
C13 C14 1.530(7) . ?
C13 C2 1.545(7) . ?
C4 H4 1.0000 . ?
C4 C3 1.527(7) . ?
C21 C26 1.401(7) . ?
C21 C22 1.400(7) . ?
C11 C6 1.396(7) . ?
C11 C10 1.382(7) . ?
C6 C7 1.398(7) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C3 C2 1.531(7) . ?
C1 C2 1.498(7) . ?
C7 H7 0.9500 . ?
C7 C8 1.377(8) . ?
C26 C25 1.395(8) . ?
C15 C20 1.377(8) . ?
C15 C16 1.381(8) . ?
C22 C23 1.398(8) . ?
C10 H10 0.9500 . ?
C10 C9 1.390(7) . ?
C2 H2 1.0000 . ?
C9 H9 0.9500 . ?
C9 C8 1.388(8) . ?
C20 H20 0.9500 . ?
C20 C19 1.387(8) . ?
C8 H8 0.9500 . ?
C23 H23 0.9500 . ?
C23 C24 1.370(9) . ?
C25 H25 0.9500 . ?
C25 C24 1.367(9) . ?
C16 H16 0.9500 . ?
C16 C17 1.384(8) . ?
C18 H18 0.9500 . ?
C18 C19 1.384(9) . ?
C18 C17 1.367(9) . ?
C19 H19 0.9500 . ?
C24 H24 0.9500 . ?
C27 H27A 0.9800 . ?
C27 H27B 0.9800 . ?
C27 H27C 0.9800 . ?
C17 H17 0.9500 . ?
C31 H31A 0.9900 . ?
C31 H31B 0.9900 . ?
C31 C32 1.482(11) . ?
C28 H28A 0.9800 . ?
C28 H28B 0.9800 . ?
C28 H28C 0.9800 . ?
C30 H30A 0.9900 . ?
C30 H30B 0.9900 . ?
C30 C29 1.487(12) . ?
C32 H32A 0.9800 . ?
C32 H32B 0.9800 . ?
C32 H32C 0.9800 . ?
C29 H29A 0.9800 . ?
C29 H29B 0.9800 . ?
C29 H29C 0.9800 . ?

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
O3 S1 O4 118.7(3) . . ?
O3 S1 N2 105.8(2) . . ?
O3 S1 N3 112.5(2) . . ?
O4 S1 N2 109.1(2) . . ?
O4 S1 N3 108.2(3) . . ?
N3 S1 N2 100.9(2) . . ?
N4 O5 H5 103(4) . . ?
C30 O6 C31 114.5(6) . . ?
C12 N2 S1 119.7(3) . . ?
C11 N2 S1 117.8(3) . . ?
C11 N2 C12 106.7(4) . . ?
O5 N4 C4 104.5(4) . . ?
C21 N4 O5 108.7(3) . . ?
C21 N4 C4 119.3(4) . . ?
C14 N1 C1 112.7(4) . . ?
C14 N1 C15 123.7(4) . . ?
C1 N1 C15 123.4(4) . . ?
C27 N3 S1 116.1(4) . . ?
C27 N3 C28 116.6(5) . . ?
C28 N3 S1 114.9(4) . . ?
C12 C5 C4 123.0(4) . . ?
C12 C5 C6 107.8(4) . . ?
C6 C5 C4 128.8(4) . . ?
C12 C13 H13 109.1 . . ?
C12 C13 C14 114.1(4) . . ?
C12 C13 C2 112.4(4) . . ?
C14 C13 H13 109.1 . . ?
C14 C13 C2 102.9(4) . . ?
C2 C13 H13 109.1 . . ?
N2 C12 C13 124.7(4) . . ?
C5 C12 N2 110.0(4) . . ?
C5 C12 C13 124.9(4) . . ?
N4 C4 H4 110.3 . . ?
N4 C4 C3 106.1(4) . . ?
C5 C4 N4 111.3(4) . . ?
C5 C4 H4 110.3 . . ?
C5 C4 C3 108.4(4) . . ?
C3 C4 H4 110.3 . . ?
C26 C21 N4 117.5(5) . . ?
C22 C21 N4 126.3(5) . . ?
C22 C21 C26 115.8(5) . . ?
C6 C11 N2 107.9(4) . . ?
C10 C11 N2 129.0(5) . . ?
C10 C11 C6 123.0(5) . . ?
O2 C14 N1 124.1(4) . . ?
O2 C14 C13 128.9(4) . . ?
N1 C14 C13 107.0(4) . . ?
C11 C6 C5 107.7(4) . . ?
C11 C6 C7 119.0(5) . . ?
C7 C6 C5 133.1(5) . . ?
C4 C3 H3A 109.3 . . ?
C4 C3 H3B 109.3 . . ?
C4 C3 C2 111.4(4) . . ?
H3A C3 H3B 108.0 . . ?
C2 C3 H3A 109.3 . . ?
C2 C3 H3B 109.3 . . ?
O1 C1 N1 124.4(5) . . ?
O1 C1 C2 127.7(5) . . ?
N1 C1 C2 107.7(4) . . ?
C6 C7 H7 120.8 . . ?
C8 C7 C6 118.5(5) . . ?
C8 C7 H7 120.8 . . ?
C21 C26 Br2 120.1(4) . . ?
C25 C26 Br2 117.4(4) . . ?
C25 C26 C21 122.4(5) . . ?
C20 C15 N1 121.1(5) . . ?
C20 C15 C16 120.3(5) . . ?
C16 C15 N1 118.6(5) . . ?
C21 C22 Br1 122.1(4) . . ?
C23 C22 Br1 116.1(4) . . ?
C23 C22 C21 121.7(5) . . ?
C11 C10 H10 121.6 . . ?
C11 C10 C9 116.7(5) . . ?
C9 C10 H10 121.6 . . ?
C13 C2 H2 110.4 . . ?
C3 C2 C13 112.8(4) . . ?
C3 C2 H2 110.4 . . ?
C1 C2 C13 103.6(4) . . ?
C1 C2 C3 109.0(4) . . ?
C1 C2 H2 110.4 . . ?
C10 C9 H9 119.4 . . ?
C8 C9 C10 121.3(5) . . ?
C8 C9 H9 119.4 . . ?
C15 C20 H20 120.3 . . ?
C15 C20 C19 119.5(6) . . ?
C19 C20 H20 120.3 . . ?
C7 C8 C9 121.5(5) . . ?
C7 C8 H8 119.3 . . ?
C9 C8 H8 119.3 . . ?
C22 C23 H23 119.9 . . ?
C24 C23 C22 120.2(6) . . ?
C24 C23 H23 119.9 . . ?
C26 C25 H25 120.2 . . ?
C24 C25 C26 119.6(6) . . ?
C24 C25 H25 120.2 . . ?
C15 C16 H16 120.1 . . ?
C15 C16 C17 119.8(6) . . ?
C17 C16 H16 120.1 . . ?
C19 C18 H18 120.0 . . ?
C17 C18 H18 120.0 . . ?
C17 C18 C19 120.1(5) . . ?
C20 C19 H19 120.0 . . ?
C18 C19 C20 120.1(6) . . ?
C18 C19 H19 120.0 . . ?
C23 C24 H24 119.9 . . ?
C25 C24 C23 120.2(6) . . ?
C25 C24 H24 119.9 . . ?
N3 C27 H27A 109.5 . . ?
N3 C27 H27B 109.5 . . ?
N3 C27 H27C 109.5 . . ?
H27A C27 H27B 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?
C16 C17 H17 119.9 . . ?
C18 C17 C16 120.2(6) . . ?
C18 C17 H17 119.9 . . ?
O6 C31 H31A 109.9 . . ?
O6 C31 H31B 109.9 . . ?
O6 C31 C32 108.8(6) . . ?
H31A C31 H31B 108.3 . . ?
C32 C31 H31A 109.9 . . ?
C32 C31 H31B 109.9 . . ?
N3 C28 H28A 109.5 . . ?
N3 C28 H28B 109.5 . . ?
N3 C28 H28C 109.5 . . ?
H28A C28 H28B 109.5 . . ?
H28A C28 H28C 109.5 . . ?
H28B C28 H28C 109.5 . . ?
O6 C30 H30A 110.0 . . ?
O6 C30 H30B 110.0 . . ?
O6 C30 C29 108.6(7) . . ?
H30A C30 H30B 108.4 . . ?
C29 C30 H30A 110.0 . . ?
C29 C30 H30B 110.0 . . ?
C31 C32 H32A 109.5 . . ?
C31 C32 H32B 109.5 . . ?
C31 C32 H32C 109.5 . . ?
H32A C32 H32B 109.5 . . ?
H32A C32 H32C 109.5 . . ?
H32B C32 H32C 109.5 . . ?
C30 C29 H29A 109.5 . . ?
C30 C29 H29B 109.5 . . ?
C30 C29 H29C 109.5 . . ?
H29A C29 H29B 109.5 . . ?
H29A C29 H29C 109.5 . . ?
H29B C29 H29C 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
Br2 C26 C25 C24 -177.9(4) . . . . ?
Br1 C22 C23 C24 178.4(4) . . . . ?
S1 N2 C12 C5 135.5(4) . . . . ?
S1 N2 C12 C13 -51.5(6) . . . . ?
S1 N2 C11 C6 -137.1(4) . . . . ?
S1 N2 C11 C10 46.7(7) . . . . ?
O5 N4 C4 C5 165.1(4) . . . . ?
O5 N4 C4 C3 -77.1(4) . . . . ?
O5 N4 C21 C26 129.5(4) . . . . ?
O5 N4 C21 C22 -43.1(6) . . . . ?
O3 S1 N2 C12 38.6(4) . . . . ?
O3 S1 N2 C11 171.0(3) . . . . ?
O3 S1 N3 C27 39.3(5) . . . . ?
O3 S1 N3 C28 -101.7(5) . . . . ?
O1 C1 C2 C13 162.9(5) . . . . ?
O1 C1 C2 C3 -76.7(7) . . . . ?
O4 S1 N2 C12 -90.2(4) . . . . ?
O4 S1 N2 C11 42.2(4) . . . . ?
O4 S1 N3 C27 172.4(4) . . . . ?
O4 S1 N3 C28 31.4(5) . . . . ?
N2 S1 N3 C27 -73.1(5) . . . . ?
N2 S1 N3 C28 145.9(5) . . . . ?
N2 C11 C6 C5 0.1(5) . . . . ?
N2 C11 C6 C7 -175.7(4) . . . . ?
N2 C11 C10 C9 175.7(5) . . . . ?
N4 C4 C3 C2 -65.1(5) . . . . ?
N4 C21 C26 Br2 5.5(6) . . . . ?
N4 C21 C26 C25 -172.5(5) . . . . ?
N4 C21 C22 Br1 -6.2(7) . . . . ?
N4 C21 C22 C23 171.5(5) . . . . ?
N1 C1 C2 C13 -21.4(5) . . . . ?
N1 C1 C2 C3 98.9(5) . . . . ?
N1 C15 C20 C19 -179.3(5) . . . . ?
N1 C15 C16 C17 179.7(5) . . . . ?
N3 S1 N2 C12 156.0(4) . . . . ?
N3 S1 N2 C11 -71.6(4) . . . . ?
C5 C4 C3 C2 54.6(5) . . . . ?
C5 C6 C7 C8 -175.3(5) . . . . ?
C12 N2 C11 C6 0.9(5) . . . . ?
C12 N2 C11 C10 -175.3(5) . . . . ?
C12 C5 C4 N4 88.6(5) . . . . ?
C12 C5 C4 C3 -27.8(6) . . . . ?
C12 C5 C6 C11 -1.1(5) . . . . ?
C12 C5 C6 C7 173.8(5) . . . . ?
C12 C13 C14 O2 39.6(7) . . . . ?
C12 C13 C14 N1 -141.4(4) . . . . ?
C12 C13 C2 C3 29.7(6) . . . . ?
C12 C13 C2 C1 147.4(4) . . . . ?
C4 N4 C21 C26 -110.9(5) . . . . ?
C4 N4 C21 C22 76.5(6) . . . . ?
C4 C5 C12 N2 174.5(4) . . . . ?
C4 C5 C12 C13 1.5(8) . . . . ?
C4 C5 C6 C11 -173.4(5) . . . . ?
C4 C5 C6 C7 1.5(9) . . . . ?
C4 C3 C2 C13 -57.8(5) . . . . ?
C4 C3 C2 C1 -172.3(4) . . . . ?
C21 N4 C4 C5 43.4(6) . . . . ?
C21 N4 C4 C3 161.2(4) . . . . ?
C21 C26 C25 C24 0.2(8) . . . . ?
C21 C22 C23 C24 0.6(8) . . . . ?
C11 N2 C12 C5 -1.6(5) . . . . ?
C11 N2 C12 C13 171.4(4) . . . . ?
C11 C6 C7 C8 -0.8(7) . . . . ?
C11 C10 C9 C8 -0.8(8) . . . . ?
C14 N1 C1 O1 -174.5(5) . . . . ?
C14 N1 C1 C2 9.7(6) . . . . ?
C14 N1 C15 C20 81.2(7) . . . . ?
C14 N1 C15 C16 -98.6(6) . . . . ?
C14 C13 C12 N2 -57.3(6) . . . . ?
C14 C13 C12 C5 114.7(5) . . . . ?
C14 C13 C2 C3 -93.5(5) . . . . ?
C14 C13 C2 C1 24.2(5) . . . . ?
C6 C5 C12 N2 1.7(5) . . . . ?
C6 C5 C12 C13 -171.4(4) . . . . ?
C6 C5 C4 N4 -100.2(6) . . . . ?
C6 C5 C4 C3 143.5(5) . . . . ?
C6 C11 C10 C9 0.0(8) . . . . ?
C6 C7 C8 C9 0.1(8) . . . . ?
C1 N1 C14 O2 -174.3(5) . . . . ?
C1 N1 C14 C13 6.7(6) . . . . ?
C1 N1 C15 C20 -104.9(6) . . . . ?
C1 N1 C15 C16 75.3(7) . . . . ?
C26 C21 C22 Br1 -179.0(4) . . . . ?
C26 C21 C22 C23 -1.3(7) . . . . ?
C26 C25 C24 C23 -1.0(9) . . . . ?
C15 N1 C14 O2 0.2(8) . . . . ?
C15 N1 C14 C13 -178.8(5) . . . . ?
C15 N1 C1 O1 11.0(8) . . . . ?
C15 N1 C1 C2 -164.8(5) . . . . ?
C15 C20 C19 C18 0.1(8) . . . . ?
C15 C16 C17 C18 -0.9(9) . . . . ?
C22 C21 C26 Br2 178.9(4) . . . . ?
C22 C21 C26 C25 0.9(8) . . . . ?
C22 C23 C24 C25 0.6(9) . . . . ?
C10 C11 C6 C5 176.5(5) . . . . ?
C10 C11 C6 C7 0.8(7) . . . . ?
C10 C9 C8 C7 0.7(9) . . . . ?
C2 C13 C12 N2 -174.0(4) . . . . ?
C2 C13 C12 C5 -2.0(7) . . . . ?
C2 C13 C14 O2 161.6(5) . . . . ?
C2 C13 C14 N1 -19.4(5) . . . . ?
C20 C15 C16 C17 -0.1(9) . . . . ?
C16 C15 C20 C19 0.5(8) . . . . ?
C19 C18 C17 C16 1.5(9) . . . . ?
C17 C18 C19 C20 -1.1(9) . . . . ?
C31 O6 C30 C29 -176.0(6) . . . . ?
C30 O6 C31 C32 175.8(6) . . . . ?

loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
0 1 0 0.0885 -0.0002 1.0007 0.0008 0.0088 0.0374 -0.0466
-2 -1 0 0.3390 -2.0021 -0.9997 -0.0008 0.0752 0.0825 0.0913
2 1 0 0.3180 2.0021 0.9997 0.0008 -0.0752 -0.0825 -0.0913
0 0 -1 0.0786 0.0003 -0.0003 -1.0010 -0.0487 0.0184 0.0072
0 0 1 0.0696 -0.0003 0.0003 1.0010 0.0487 -0.0184 -0.0072
0 -1 0 0.0675 0.0002 -1.0007 -0.0008 -0.0088 -0.0374 0.0466

_olex2_submission_special_instructions 'No special instructions were received'
_vrf_DIFMX01_mjh69               
;
PROBLEM: The maximum difference density is > 0.1*ZMAX*1.00
RESPONSE: There is a minor satellite crystal causing parasitic
diffraction - see refinement details for further information
;
_vrf_PLAT094_mjh69               
;
PROBLEM: Ratio of Maximum / Minimum Residual Density ....       4.09 Report
RESPONSE: There is unresoved residual density due to parasitic diffractio
from a minor satellite crystal - see refinement details for further 
information
;
_vrf_PLAT097_mjh69               
;
PROBLEM: Large Reported Max.  (Positive) Residual Density       3.75 eA-3  
RESPONSE: There is unresoved residual density due to parasitic diffractio
from a minor satellite crystal - see refinement details for further 
information
;
_vrf_PLAT971_mjh69               
;
PROBLEM: Check Calcd Residual Density
RESPONSE: There is unresoved residual density due to parasitic diffractio
from a minor satellite crystal - see refinement details for further 
information
;
