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

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

data_pac1201
_database_code_depnum_ccdc_archive 'CCDC 1417066'
_audit_update_record             
;
2015-08-05 deposited with the CCDC.
2015-11-24 downloaded from the CCDC.
;
_audit_creation_date             2012-12-20
_audit_creation_method           
;
  Olex2 1.2
  (compiled Dec  5 2012 16:17:34, GUI svn.r4385)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C15 H21 N O S'
_chemical_formula_sum            'C15 H21 N O S'
_chemical_formula_weight         263.39
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C15 H21 N1 O1 S1'
_chemical_oxdiff_usercomment     'Joshua jcs-1-25-1'
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'

_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_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x+1/2, y+1/2, -z+1/2'
3 '-x, -y, -z'
4 'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   8.24752(10)
_cell_length_b                   12.75550(14)
_cell_length_c                   13.60131(17)
_cell_angle_alpha                90.00
_cell_angle_beta                 100.4273(12)
_cell_angle_gamma                90.00
_cell_volume                     1407.24(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9517
_cell_measurement_temperature    110.05(10)
_cell_measurement_theta_max      29.9654
_cell_measurement_theta_min      2.9701
_exptl_absorpt_coefficient_mu    0.219
_exptl_absorpt_correction_T_max  0.981
_exptl_absorpt_correction_T_min  0.969
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET)
(compiled Sep 14 2012,17:21:16)
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_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.243
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             568
_exptl_crystal_size_max          0.1998
_exptl_crystal_size_mid          0.1883
_exptl_crystal_size_min          0.1512
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0275
_diffrn_reflns_av_unetI/netI     0.0241
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            15785
_diffrn_reflns_theta_full        29.97
_diffrn_reflns_theta_max         30.03
_diffrn_reflns_theta_min         2.98
_diffrn_ambient_temperature      110.05(10)
_diffrn_detector_area_resol_mean 16.1450
_diffrn_measured_fraction_theta_full 0.9960
_diffrn_measured_fraction_theta_max 0.9884
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -97.00   31.00   1.0000   25.0000
omega____ theta____ kappa____ phi______ frames
    -      -25.0740    0.0000  -30.0000 128

#__ type_ start__ end____ width___ exp.time_
  2 omega  -60.00   19.00   1.0000   25.0000
omega____ theta____ kappa____ phi______ frames
    -      -25.0740   97.0000  -44.0000 79

#__ type_ start__ end____ width___ exp.time_
  3 omega   64.00  102.00   1.0000   25.0000
omega____ theta____ kappa____ phi______ frames
    -       26.3240  178.0000  150.0000 38

#__ type_ start__ end____ width___ exp.time_
  4 omega  -94.00   -4.00   1.0000   25.0000
omega____ theta____ kappa____ phi______ frames
    -      -25.0740  -57.0000  150.0000 90

#__ type_ start__ end____ width___ exp.time_
  5 omega -102.00  -34.00   1.0000   25.0000
omega____ theta____ kappa____ phi______ frames
    -      -25.0740  178.0000   30.0000 68

#__ type_ start__ end____ width___ exp.time_
  6 omega  -95.00  -70.00   1.0000   25.0000
omega____ theta____ kappa____ phi______ frames
    -      -25.0740  -77.0000   30.0000 25

#__ type_ start__ end____ width___ exp.time_
  7 omega  -95.00    5.00   1.0000   25.0000
omega____ theta____ kappa____ phi______ frames
    -      -25.0740  -77.0000  -90.0000 100
;
_diffrn_measurement_device_type  'SuperNova, Single source at offset), Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0138358000
_diffrn_orient_matrix_UB_12      -0.0540225000
_diffrn_orient_matrix_UB_13      -0.0077575000
_diffrn_orient_matrix_UB_21      -0.0460594000
_diffrn_orient_matrix_UB_22      0.0038465000
_diffrn_orient_matrix_UB_23      -0.0492253000
_diffrn_orient_matrix_UB_31      0.0730132000
_diffrn_orient_matrix_UB_32      0.0126909000
_diffrn_orient_matrix_UB_33      -0.0180961000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                3647
_reflns_number_total             4109
_reflns_odcompleteness_completeness 99.60
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     29.97
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET)
(compiled Sep 14 2012,17:21:16)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET)
(compiled Sep 14 2012,17:21:16)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET)
(compiled Sep 14 2012,17:21:16)
;
_computing_molecular_graphics    
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material  
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement  
;
SHELXL, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution    'SUPERFLIP, J. Appl. Cryst. (2007) 40, 786-790'
_refine_diff_density_max         0.453
_refine_diff_density_min         -0.225
_refine_diff_density_rms         0.048
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     170
_refine_ls_number_reflns         4109
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0377
_refine_ls_R_factor_gt           0.0330
_refine_ls_restrained_S_all      1.038
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0386P)²+0.5714P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0841
_refine_ls_wR_factor_ref         0.0879
_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  H9 of C9, H8 of C8, H7 of C7, H3 of C3, H4 of C4, {H2A,H2B} of C2, H6 of C6,
   H10 of C10, {H1A,H1B} of C1
 At 1.5 times of:
  {H15A,H15B,H15C} of C15, {H14A,H14B,H14C} of C14, {H13A,H13B,H13C} of C13
2.a Ternary CH refined with riding coordinates:
 C3(H3), C4(H4)
2.b Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C1(H1A,H1B)
2.c Aromatic/amide H refined with riding coordinates:
 C6(H6), C10(H10), C9(H9), C7(H7), C8(H8)
2.d Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C), C15(H15A,H15B,H15C), C13(H13A,H13B,H13C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   difmap
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.59453(3) 0.25962(2) 1.038922(19) 0.01721(8) Uani 1 1 d . . .
O1 O 0.39064(9) 0.52442(6) 0.83367(6) 0.01892(16) Uani 1 1 d . . .
N1 N 0.37801(10) 0.30125(6) 0.87977(6) 0.01258(16) Uani 1 1 d . . .
C12 C 0.26019(12) 0.19760(8) 1.00353(7) 0.01506(18) Uani 1 1 d . . .
C11 C 0.40248(12) 0.25663(7) 0.96894(7) 0.01263(18) Uani 1 1 d . . .
C5 C 0.68166(12) 0.50676(7) 0.81885(7) 0.01327(18) Uani 1 1 d . . .
C3 C 0.50182(12) 0.35213(7) 0.82923(7) 0.01288(17) Uani 1 1 d . . .
H3 H 0.6046 0.3094 0.8343 0.015 Uiso 1 1 calc R . .
C4 C 0.53820(11) 0.46550(8) 0.86282(7) 0.01291(17) Uani 1 1 d . . .
H4 H 0.5691 0.4669 0.9374 0.015 Uiso 1 1 calc R . .
C2 C 0.38383(13) 0.33618(8) 0.72775(7) 0.01567(19) Uani 1 1 d . . .
H2A H 0.3533 0.4020 0.6905 0.019 Uiso 1 1 calc R . .
H2B H 0.4219 0.2826 0.6844 0.019 Uiso 1 1 calc R . .
C6 C 0.65827(14) 0.55883(8) 0.72766(8) 0.0190(2) Uani 1 1 d . . .
H6 H 0.5497 0.5719 0.6926 0.023 Uiso 1 1 calc R . .
C10 C 0.84170(13) 0.48843(8) 0.86980(9) 0.0187(2) Uani 1 1 d . . .
H10 H 0.8586 0.4527 0.9321 0.022 Uiso 1 1 calc R . .
C1 C 0.25173(12) 0.29613(8) 0.78575(7) 0.01480(18) Uani 1 1 d . . .
H1A H 0.1582 0.3450 0.7847 0.018 Uiso 1 1 calc R . .
H1B H 0.2123 0.2243 0.7671 0.018 Uiso 1 1 calc R . .
C14 C 0.25691(14) 0.08593(8) 0.96017(8) 0.0195(2) Uani 1 1 d . . .
H14A H 0.2377 0.0896 0.8870 0.029 Uiso 1 1 calc R . .
H14B H 0.1682 0.0457 0.9815 0.029 Uiso 1 1 calc R . .
H14C H 0.3628 0.0515 0.9844 0.029 Uiso 1 1 calc R . .
C9 C 0.97664(14) 0.52213(9) 0.82997(10) 0.0260(2) Uani 1 1 d . . .
H9 H 1.0854 0.5102 0.8653 0.031 Uiso 1 1 calc R . .
C15 C 0.28916(16) 0.18968(9) 1.11793(8) 0.0232(2) Uani 1 1 d . . .
H15A H 0.3933 0.1531 1.1418 0.035 Uiso 1 1 calc R . .
H15B H 0.1984 0.1506 1.1383 0.035 Uiso 1 1 calc R . .
H15C H 0.2943 0.2603 1.1468 0.035 Uiso 1 1 calc R . .
C7 C 0.79373(17) 0.59196(9) 0.68748(9) 0.0263(3) Uani 1 1 d . . .
H7 H 0.7774 0.6274 0.6250 0.032 Uiso 1 1 calc R . .
C8 C 0.95187(16) 0.57314(10) 0.73867(10) 0.0294(3) Uani 1 1 d . . .
H8 H 1.0440 0.5954 0.7110 0.035 Uiso 1 1 calc R . .
C13 C 0.09335(13) 0.25243(9) 0.96957(9) 0.0207(2) Uani 1 1 d . . .
H13A H 0.1023 0.3261 0.9902 0.031 Uiso 1 1 calc R . .
H13B H 0.0089 0.2178 1.0003 0.031 Uiso 1 1 calc R . .
H13C H 0.0626 0.2483 0.8966 0.031 Uiso 1 1 calc R . .
H1 H 0.401(2) 0.5815(14) 0.8663(13) 0.036(4) Uiso 1 1 d . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 C11 1.6943(10) . ?
O1 C4 1.4243(12) . ?
N1 C11 1.3217(12) . ?
N1 C3 1.4801(12) . ?
N1 C1 1.4974(12) . ?
C12 C11 1.5380(14) . ?
C12 C14 1.5400(14) . ?
C12 C15 1.5342(15) . ?
C12 C13 1.5382(15) . ?
C5 C4 1.5135(13) . ?
C5 C6 1.3893(14) . ?
C5 C10 1.3950(14) . ?
C3 C4 1.5297(13) . ?
C3 C2 1.5515(13) . ?
C2 C1 1.5432(14) . ?
C6 C7 1.3951(16) . ?
C10 C9 1.3911(16) . ?
C9 C8 1.384(2) . ?
C7 C8 1.384(2) . ?

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
C11 N1 C3 127.69(8) . . ?
C11 N1 C1 137.05(8) . . ?
C3 N1 C1 93.10(7) . . ?
C11 C12 C14 107.29(8) . . ?
C11 C12 C13 112.09(8) . . ?
C15 C12 C11 110.80(8) . . ?
C15 C12 C14 108.44(9) . . ?
C15 C12 C13 107.53(9) . . ?
C13 C12 C14 110.66(9) . . ?
N1 C11 S1 118.54(7) . . ?
N1 C11 C12 119.56(8) . . ?
C12 C11 S1 121.78(7) . . ?
C6 C5 C4 121.79(9) . . ?
C6 C5 C10 119.31(9) . . ?
C10 C5 C4 118.85(9) . . ?
N1 C3 C4 112.97(8) . . ?
N1 C3 C2 88.93(7) . . ?
C4 C3 C2 116.57(8) . . ?
O1 C4 C5 113.34(8) . . ?
O1 C4 C3 107.71(8) . . ?
C5 C4 C3 109.62(8) . . ?
C1 C2 C3 88.61(7) . . ?
C5 C6 C7 120.19(11) . . ?
C9 C10 C5 120.44(11) . . ?
N1 C1 C2 88.62(7) . . ?
C8 C9 C10 119.74(11) . . ?
C8 C7 C6 119.93(11) . . ?
C9 C8 C7 120.38(10) . . ?

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 S1 0.849(18) 2.399(18) 3.2449(8) 174.6(15) 3_667

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
1 0 1 0.0530 0.9992 0.0011 1.0014 0.0060 -0.0953 0.0548
0 1 0 0.0836 -0.0007 0.9991 -0.0010 -0.0540 0.0039 0.0126
-1 -2 1 0.0730 -0.9998 -1.9993 1.0032 0.0864 -0.0110 -0.1165
-1 0 1 0.0870 -1.0012 -0.0011 1.0011 -0.0216 -0.0032 -0.0912
0 1 -2 0.0549 0.0013 0.9991 -2.0036 -0.0384 0.1024 0.0490
1 -2 -2 0.0838 1.0035 -1.9971 -2.0004 0.1373 0.0446 0.0841
-1 -1 0 0.0537 -0.9995 -1.0002 0.0009 0.0402 0.0421 -0.0857
0 1 1 0.0657 -0.0017 0.9991 1.0003 -0.0618 -0.0453 -0.0055
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Chloroform/pentane'
####################################################################### 
# 
# 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_pac1202
_database_code_depnum_ccdc_archive 'CCDC 1417067'
_audit_update_record             
;
2015-08-05 deposited with the CCDC.
2015-11-24 downloaded from the CCDC.
;
_audit_creation_date             2015-01-15
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.01.12 svn.r3133 for OlexSys, GUI svn.r4987)
;
_shelxl_version_number           2013-4
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C15 H21 N O S'
_chemical_formula_sum            'C15 H21 N O S'
_chemical_formula_weight         263.39
_chemical_absolute_configuration syn
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C15 H21 N1 O1 S1'
_chemical_oxdiff_usercomment     'Joshua jcs-1-25-2'
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      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'

_cell_length_a                   7.0524(3)
_cell_length_b                   17.7693(8)
_cell_length_c                   22.6194(7)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2834.56(19)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    4278
_cell_measurement_temperature    110.00(10)
_cell_measurement_theta_max      30.2129
_cell_measurement_theta_min      2.9097
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.217
_exptl_absorpt_correction_T_max  0.999
_exptl_absorpt_correction_T_min  0.997
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET)
(compiled Sep 14 2012,17:21:16)
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_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.234
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1136
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Chloroform/pentane'
_exptl_crystal_size_max          0.2128
_exptl_crystal_size_mid          0.1273
_exptl_crystal_size_min          0.0856
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0431
_diffrn_reflns_av_unetI/netI     0.0701
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.885
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            12242
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.801
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         30.280
_diffrn_reflns_theta_min         2.916
_diffrn_ambient_temperature      110.00(10)
_diffrn_detector_area_resol_mean 16.1450
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.885
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -88.00  -60.00   1.0000  120.0000
omega____ theta____ kappa____ phi______ frames
    -      -20.6164 -178.0000   90.0000 28

#__ type_ start__ end____ width___ exp.time_
  2 omega  -22.00   91.00   1.0000  120.0000
omega____ theta____ kappa____ phi______ frames
    -       21.8664   19.0000   90.0000 113

#__ type_ start__ end____ width___ exp.time_
  3 omega  -51.00    5.00   1.0000  120.0000
omega____ theta____ kappa____ phi______ frames
    -      -20.6164   77.0000    0.0000 56
;
_diffrn_measurement_device_type  'SuperNova, Single source at offset), Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0758696000
_diffrn_orient_matrix_UB_12      0.0105519000
_diffrn_orient_matrix_UB_13      -0.0188535000
_diffrn_orient_matrix_UB_21      0.0154775000
_diffrn_orient_matrix_UB_22      0.0383395000
_diffrn_orient_matrix_UB_23      0.0072291000
_diffrn_orient_matrix_UB_31      0.0642945000
_diffrn_orient_matrix_UB_32      0.0032479000
_diffrn_orient_matrix_UB_33      -0.0239833000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_reflns_Friedel_coverage         0.611
_reflns_Friedel_fraction_full    0.882
_reflns_Friedel_fraction_max     0.694
_reflns_number_gt                5679
_reflns_number_total             6773
_reflns_odcompleteness_completeness 99.72
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     27.82
_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 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET)
(compiled Sep 14 2012,17:21:16)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET)
(compiled Sep 14 2012,17:21:16)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET)
(compiled Sep 14 2012,17:21:16)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_refine_diff_density_max         2.116
_refine_diff_density_min         -0.354
_refine_diff_density_rms         0.103
_refine_ls_abs_structure_details 
;
 Flack x determined using 1951 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   0.05(6)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     339
_refine_ls_number_reflns         6773
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0820
_refine_ls_R_factor_gt           0.0691
_refine_ls_restrained_S_all      1.058
_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)+(0.1072P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1650
_refine_ls_wR_factor_ref         0.1787
_refine_special_details          
;
There are 4 large electron density peaks in the map that are probably due to
 sulphur atoms in 2 more non-merohedrally twinned molecules, since the distance
 between the pairs of electron density peaks is similar to that in the modelled
 structure.
 Attempts were made to model these twinned molecules, but it was not possible.
;
_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:
 C7(H7), C8(H8), C22(H22), C23(H23)
2.b Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B), C10(H10A,H10B), C24(H24A,H24B), C25(H25A,H25B)
2.c Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4), C5(H5), C16(H16), C17(H17), C18(H18),
 C19(H19), C20(H20)
2.d Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C), C14(H14A,H14B,H14C), C15(H15A,H15B,H15C), C28(H28A,H28B,
 H28C), C29(H29A,H29B,H29C), C30(H30A,H30B,H30C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.7255(5) 0.5017(2) 0.14164(17) 0.0136(8) Uani 1 1 d . . . . .
H1 H 0.7750 0.5333 0.1718 0.016 Uiso 1 1 calc R . . . .
C2 C 0.7885(6) 0.5097(2) 0.08354(17) 0.0170(8) Uani 1 1 d . . . . .
H2 H 0.8805 0.5469 0.0742 0.020 Uiso 1 1 calc R . . . .
C3 C 0.7172(6) 0.4636(2) 0.03928(16) 0.0167(8) Uani 1 1 d . . . . .
H3 H 0.7604 0.4690 -0.0003 0.020 Uiso 1 1 calc R . . . .
C4 C 0.5826(6) 0.4095(2) 0.05309(16) 0.0175(8) Uani 1 1 d . . . . .
H4 H 0.5340 0.3776 0.0230 0.021 Uiso 1 1 calc R . . . .
C5 C 0.5187(5) 0.4018(2) 0.11098(16) 0.0130(8) Uani 1 1 d . . . . .
H5 H 0.4253 0.3651 0.1201 0.016 Uiso 1 1 calc R . . . .
C6 C 0.5900(6) 0.4474(2) 0.15550(16) 0.0119(7) Uani 1 1 d . . . . .
C7 C 0.5220(5) 0.4383(2) 0.21874(15) 0.0114(7) Uani 1 1 d . . . . .
H7 H 0.4394 0.3926 0.2206 0.014 Uiso 1 1 calc R . . . .
C8 C 0.4041(6) 0.5058(2) 0.23771(15) 0.0120(7) Uani 1 1 d . . . . .
H8 H 0.4767 0.5541 0.2372 0.014 Uiso 1 1 calc R . . . .
C9 C 0.2109(5) 0.5110(3) 0.20553(16) 0.0162(8) Uani 1 1 d . . . . .
H9A H 0.1766 0.5627 0.1931 0.019 Uiso 1 1 calc R . . . .
H9B H 0.1973 0.4751 0.1723 0.019 Uiso 1 1 calc R . . . .
C10 C 0.1126(5) 0.4854(2) 0.26253(16) 0.0142(8) Uani 1 1 d . . . . .
H10A H 0.0133 0.5204 0.2767 0.017 Uiso 1 1 calc R . . . .
H10B H 0.0647 0.4330 0.2611 0.017 Uiso 1 1 calc R . . . .
C11 C 0.3530(6) 0.5027(2) 0.34945(16) 0.0117(8) Uani 1 1 d . . . . .
C12 C 0.2035(5) 0.4958(2) 0.39886(16) 0.0135(8) Uani 1 1 d . . . . .
C13 C 0.2968(7) 0.4879(3) 0.45954(16) 0.0228(10) Uani 1 1 d . . . . .
H13A H 0.3792 0.4435 0.4597 0.034 Uiso 1 1 calc GR . . . .
H13B H 0.1985 0.4822 0.4899 0.034 Uiso 1 1 calc GR . . . .
H13C H 0.3725 0.5329 0.4679 0.034 Uiso 1 1 calc GR . . . .
C14 C 0.0742(7) 0.4275(2) 0.38998(18) 0.0212(9) Uani 1 1 d . . . . .
H14A H -0.0048 0.4353 0.3549 0.032 Uiso 1 1 calc GR . . . .
H14B H -0.0072 0.4213 0.4247 0.032 Uiso 1 1 calc GR . . . .
H14C H 0.1518 0.3823 0.3846 0.032 Uiso 1 1 calc GR . . . .
C15 C 0.0874(6) 0.5692(2) 0.39896(16) 0.0185(8) Uani 1 1 d . . . . .
H15A H 0.1699 0.6115 0.4097 0.028 Uiso 1 1 calc GR . . . .
H15B H -0.0159 0.5652 0.4278 0.028 Uiso 1 1 calc GR . . . .
H15C H 0.0342 0.5778 0.3595 0.028 Uiso 1 1 calc GR . . . .
N1 N 0.2981(4) 0.49351(19) 0.29374(13) 0.0105(6) Uani 1 1 d . . . . .
O1 O 0.6820(4) 0.42569(17) 0.25560(12) 0.0166(6) Uani 1 1 d . . . . .
H1A H 0.666(7) 0.453(3) 0.286(2) 0.026(14) Uiso 1 1 d . . . . .
S1 S 0.57956(14) 0.52551(6) 0.36441(4) 0.0165(2) Uani 1 1 d . . . . .
C16 C -0.2167(5) 0.7220(2) 0.35898(17) 0.0140(8) Uani 1 1 d . . . . .
H16 H -0.2651 0.6896 0.3292 0.017 Uiso 1 1 calc R . . . .
C17 C -0.2796(6) 0.7146(2) 0.41694(17) 0.0184(9) Uani 1 1 d . . . . .
H17 H -0.3702 0.6771 0.4268 0.022 Uiso 1 1 calc R . . . .
C18 C -0.2096(6) 0.7623(3) 0.46051(17) 0.0184(9) Uani 1 1 d . . . . .
H18 H -0.2528 0.7576 0.5001 0.022 Uiso 1 1 calc R . . . .
C19 C -0.0775(6) 0.8166(2) 0.44622(16) 0.0163(8) Uani 1 1 d . . . . .
H19 H -0.0296 0.8491 0.4760 0.020 Uiso 1 1 calc R . . . .
C20 C -0.0142(5) 0.8237(2) 0.38821(16) 0.0135(8) Uani 1 1 d . . . . .
H20 H 0.0769 0.8611 0.3784 0.016 Uiso 1 1 calc R . . . .
C21 C -0.0841(6) 0.7762(2) 0.34464(15) 0.0109(7) Uani 1 1 d . . . . .
C22 C -0.0148(5) 0.7851(2) 0.28115(15) 0.0109(7) Uani 1 1 d . . . . .
H22 H 0.0663 0.8312 0.2791 0.013 Uiso 1 1 calc R . . . .
C23 C 0.1050(5) 0.7177(2) 0.26211(15) 0.0119(8) Uani 1 1 d . . . . .
H23 H 0.0326 0.6693 0.2629 0.014 Uiso 1 1 calc R . . . .
C24 C 0.2962(5) 0.7124(2) 0.29449(15) 0.0145(8) Uani 1 1 d . . . . .
H24A H 0.3291 0.6608 0.3075 0.017 Uiso 1 1 calc R . . . .
H24B H 0.3101 0.7488 0.3273 0.017 Uiso 1 1 calc R . . . .
C25 C 0.3960(6) 0.7367(2) 0.23707(16) 0.0149(8) Uani 1 1 d . . . . .
H25A H 0.4458 0.7888 0.2381 0.018 Uiso 1 1 calc R . . . .
H25B H 0.4940 0.7009 0.2233 0.018 Uiso 1 1 calc R . . . .
C26 C 0.1548(5) 0.7195(2) 0.15029(16) 0.0122(7) Uani 1 1 d . . . . .
C27 C 0.3050(5) 0.7272(2) 0.10071(15) 0.0135(8) Uani 1 1 d . . . . .
C28 C 0.2069(6) 0.7372(3) 0.04085(16) 0.0221(10) Uani 1 1 d . . . . .
H28A H 0.1287 0.6928 0.0324 0.033 Uiso 1 1 calc GR . . . .
H28B H 0.3028 0.7429 0.0098 0.033 Uiso 1 1 calc GR . . . .
H28C H 0.1263 0.7821 0.0420 0.033 Uiso 1 1 calc GR . . . .
C29 C 0.4336(7) 0.7953(2) 0.11035(17) 0.0203(9) Uani 1 1 d . . . . .
H29A H 0.3556 0.8400 0.1177 0.030 Uiso 1 1 calc GR . . . .
H29B H 0.5115 0.8035 0.0751 0.030 Uiso 1 1 calc GR . . . .
H29C H 0.5160 0.7862 0.1445 0.030 Uiso 1 1 calc GR . . . .
C30 C 0.4202(6) 0.6541(2) 0.09862(17) 0.0196(8) Uani 1 1 d . . . . .
H30A H 0.4827 0.6462 0.1368 0.029 Uiso 1 1 calc GR . . . .
H30B H 0.5162 0.6577 0.0674 0.029 Uiso 1 1 calc GR . . . .
H30C H 0.3353 0.6118 0.0903 0.029 Uiso 1 1 calc GR . . . .
N2 N 0.2103(4) 0.72916(19) 0.20580(13) 0.0107(6) Uani 1 1 d . . . . .
O2 O -0.1761(4) 0.79649(17) 0.24438(12) 0.0167(6) Uani 1 1 d . . . . .
H2A H -0.168(7) 0.770(3) 0.212(2) 0.026(14) Uiso 1 1 d . . . . .
S2 S -0.07188(14) 0.69718(6) 0.13571(4) 0.0174(2) Uani 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
C1 H1 0.9500 . ?
C1 C2 1.395(5) . ?
C1 C6 1.393(5) . ?
C2 H2 0.9500 . ?
C2 C3 1.388(6) . ?
C3 H3 0.9500 . ?
C3 C4 1.387(6) . ?
C4 H4 0.9500 . ?
C4 C5 1.391(5) . ?
C5 H5 0.9500 . ?
C5 C6 1.387(5) . ?
C6 C7 1.518(5) . ?
C7 H7 1.0000 . ?
C7 C8 1.521(5) . ?
C7 O1 1.421(4) . ?
C8 H8 1.0000 . ?
C8 C9 1.548(5) . ?
C8 N1 1.488(4) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C9 C10 1.533(5) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C10 N1 1.493(5) . ?
C11 C12 1.541(5) . ?
C11 N1 1.328(5) . ?
C11 S1 1.683(4) . ?
C12 C13 1.529(5) . ?
C12 C14 1.531(6) . ?
C12 C15 1.541(5) . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
O1 H1A 0.84(5) . ?
C16 H16 0.9500 . ?
C16 C17 1.390(5) . ?
C16 C21 1.381(5) . ?
C17 H17 0.9500 . ?
C17 C18 1.390(6) . ?
C18 H18 0.9500 . ?
C18 C19 1.379(6) . ?
C19 H19 0.9500 . ?
C19 C20 1.392(5) . ?
C20 H20 0.9500 . ?
C20 C21 1.389(5) . ?
C21 C22 1.526(5) . ?
C22 H22 1.0000 . ?
C22 C23 1.529(5) . ?
C22 O2 1.423(4) . ?
C23 H23 1.0000 . ?
C23 C24 1.538(5) . ?
C23 N2 1.488(4) . ?
C24 H24A 0.9900 . ?
C24 H24B 0.9900 . ?
C24 C25 1.539(5) . ?
C25 H25A 0.9900 . ?
C25 H25B 0.9900 . ?
C25 N2 1.494(5) . ?
C26 C27 1.549(5) . ?
C26 N2 1.326(4) . ?
C26 S2 1.680(4) . ?
C27 C28 1.531(5) . ?
C27 C29 1.528(5) . ?
C27 C30 1.533(5) . ?
C28 H28A 0.9800 . ?
C28 H28B 0.9800 . ?
C28 H28C 0.9800 . ?
C29 H29A 0.9800 . ?
C29 H29B 0.9800 . ?
C29 H29C 0.9800 . ?
C30 H30A 0.9800 . ?
C30 H30B 0.9800 . ?
C30 H30C 0.9800 . ?
O2 H2A 0.88(5) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 H1 120.0 . . ?
C6 C1 H1 120.0 . . ?
C6 C1 C2 120.1(4) . . ?
C1 C2 H2 119.9 . . ?
C3 C2 C1 120.2(4) . . ?
C3 C2 H2 119.9 . . ?
C2 C3 H3 120.2 . . ?
C4 C3 C2 119.7(3) . . ?
C4 C3 H3 120.2 . . ?
C3 C4 H4 120.0 . . ?
C3 C4 C5 120.1(4) . . ?
C5 C4 H4 120.0 . . ?
C4 C5 H5 119.7 . . ?
C6 C5 C4 120.6(4) . . ?
C6 C5 H5 119.7 . . ?
C1 C6 C7 120.2(3) . . ?
C5 C6 C1 119.3(3) . . ?
C5 C6 C7 120.5(3) . . ?
C6 C7 H7 108.1 . . ?
C6 C7 C8 110.8(3) . . ?
C8 C7 H7 108.1 . . ?
O1 C7 C6 108.6(3) . . ?
O1 C7 H7 108.1 . . ?
O1 C7 C8 113.1(3) . . ?
C7 C8 H8 113.2 . . ?
C7 C8 C9 113.3(3) . . ?
C9 C8 H8 113.2 . . ?
N1 C8 C7 113.5(3) . . ?
N1 C8 H8 113.2 . . ?
N1 C8 C9 88.1(3) . . ?
C8 C9 H9A 113.8 . . ?
C8 C9 H9B 113.8 . . ?
H9A C9 H9B 111.0 . . ?
C10 C9 C8 89.1(3) . . ?
C10 C9 H9A 113.8 . . ?
C10 C9 H9B 113.8 . . ?
C9 C10 H10A 113.9 . . ?
C9 C10 H10B 113.9 . . ?
H10A C10 H10B 111.1 . . ?
N1 C10 C9 88.4(3) . . ?
N1 C10 H10A 113.9 . . ?
N1 C10 H10B 113.9 . . ?
C12 C11 S1 121.5(3) . . ?
N1 C11 C12 118.6(3) . . ?
N1 C11 S1 119.8(3) . . ?
C13 C12 C11 111.3(3) . . ?
C13 C12 C14 107.5(3) . . ?
C13 C12 C15 107.8(3) . . ?
C14 C12 C11 112.0(3) . . ?
C14 C12 C15 110.8(3) . . ?
C15 C12 C11 107.3(3) . . ?
C12 C13 H13A 109.5 . . ?
C12 C13 H13B 109.5 . . ?
C12 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C12 C14 H14A 109.5 . . ?
C12 C14 H14B 109.5 . . ?
C12 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C12 C15 H15A 109.5 . . ?
C12 C15 H15B 109.5 . . ?
C12 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C8 N1 C10 93.0(3) . . ?
C11 N1 C8 130.1(3) . . ?
C11 N1 C10 135.7(3) . . ?
C7 O1 H1A 106(4) . . ?
C17 C16 H16 119.9 . . ?
C21 C16 H16 119.9 . . ?
C21 C16 C17 120.2(4) . . ?
C16 C17 H17 120.1 . . ?
C16 C17 C18 119.9(4) . . ?
C18 C17 H17 120.1 . . ?
C17 C18 H18 120.0 . . ?
C19 C18 C17 120.0(4) . . ?
C19 C18 H18 120.0 . . ?
C18 C19 H19 120.0 . . ?
C18 C19 C20 120.1(4) . . ?
C20 C19 H19 120.0 . . ?
C19 C20 H20 120.0 . . ?
C21 C20 C19 120.0(4) . . ?
C21 C20 H20 120.0 . . ?
C16 C21 C20 119.9(3) . . ?
C16 C21 C22 120.7(3) . . ?
C20 C21 C22 119.4(3) . . ?
C21 C22 H22 108.3 . . ?
C21 C22 C23 111.1(3) . . ?
C23 C22 H22 108.3 . . ?
O2 C22 C21 108.0(3) . . ?
O2 C22 H22 108.3 . . ?
O2 C22 C23 112.8(3) . . ?
C22 C23 H23 112.8 . . ?
C22 C23 C24 113.5(3) . . ?
C24 C23 H23 112.8 . . ?
N2 C23 C22 114.1(3) . . ?
N2 C23 H23 112.8 . . ?
N2 C23 C24 88.8(3) . . ?
C23 C24 H24A 113.8 . . ?
C23 C24 H24B 113.8 . . ?
C23 C24 C25 89.0(3) . . ?
H24A C24 H24B 111.0 . . ?
C25 C24 H24A 113.8 . . ?
C25 C24 H24B 113.8 . . ?
C24 C25 H25A 113.9 . . ?
C24 C25 H25B 113.9 . . ?
H25A C25 H25B 111.1 . . ?
N2 C25 C24 88.5(3) . . ?
N2 C25 H25A 113.9 . . ?
N2 C25 H25B 113.9 . . ?
C27 C26 S2 122.0(3) . . ?
N2 C26 C27 118.2(3) . . ?
N2 C26 S2 119.8(3) . . ?
C28 C27 C26 109.9(3) . . ?
C28 C27 C30 108.1(3) . . ?
C29 C27 C26 111.9(3) . . ?
C29 C27 C28 107.7(3) . . ?
C29 C27 C30 111.2(3) . . ?
C30 C27 C26 108.1(3) . . ?
C27 C28 H28A 109.5 . . ?
C27 C28 H28B 109.5 . . ?
C27 C28 H28C 109.5 . . ?
H28A C28 H28B 109.5 . . ?
H28A C28 H28C 109.5 . . ?
H28B C28 H28C 109.5 . . ?
C27 C29 H29A 109.5 . . ?
C27 C29 H29B 109.5 . . ?
C27 C29 H29C 109.5 . . ?
H29A C29 H29B 109.5 . . ?
H29A C29 H29C 109.5 . . ?
H29B C29 H29C 109.5 . . ?
C27 C30 H30A 109.5 . . ?
C27 C30 H30B 109.5 . . ?
C27 C30 H30C 109.5 . . ?
H30A C30 H30B 109.5 . . ?
H30A C30 H30C 109.5 . . ?
H30B C30 H30C 109.5 . . ?
C23 N2 C25 92.5(3) . . ?
C26 N2 C23 130.2(3) . . ?
C26 N2 C25 135.9(3) . . ?
C22 O2 H2A 111(3) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C1 C2 C3 C4 0.1(6) . . . . ?
C1 C6 C7 C8 69.3(4) . . . . ?
C1 C6 C7 O1 -55.5(5) . . . . ?
C2 C1 C6 C5 -0.2(6) . . . . ?
C2 C1 C6 C7 179.7(3) . . . . ?
C2 C3 C4 C5 0.4(6) . . . . ?
C3 C4 C5 C6 -0.8(6) . . . . ?
C4 C5 C6 C1 0.7(6) . . . . ?
C4 C5 C6 C7 -179.2(4) . . . . ?
C5 C6 C7 C8 -110.9(4) . . . . ?
C5 C6 C7 O1 124.3(4) . . . . ?
C6 C1 C2 C3 -0.2(6) . . . . ?
C6 C7 C8 C9 68.7(4) . . . . ?
C6 C7 C8 N1 167.3(3) . . . . ?
C7 C8 C9 C10 106.2(3) . . . . ?
C7 C8 N1 C10 -105.7(3) . . . . ?
C7 C8 N1 C11 85.7(5) . . . . ?
C8 C9 C10 N1 8.6(3) . . . . ?
C9 C8 N1 C10 8.9(3) . . . . ?
C9 C8 N1 C11 -159.6(4) . . . . ?
C9 C10 N1 C8 -9.0(3) . . . . ?
C9 C10 N1 C11 158.4(5) . . . . ?
C12 C11 N1 C8 171.8(4) . . . . ?
C12 C11 N1 C10 8.4(7) . . . . ?
N1 C8 C9 C10 -8.7(3) . . . . ?
N1 C11 C12 C13 165.5(4) . . . . ?
N1 C11 C12 C14 45.0(5) . . . . ?
N1 C11 C12 C15 -76.8(4) . . . . ?
O1 C7 C8 C9 -169.1(3) . . . . ?
O1 C7 C8 N1 -70.6(4) . . . . ?
S1 C11 C12 C13 -17.5(5) . . . . ?
S1 C11 C12 C14 -138.0(3) . . . . ?
S1 C11 C12 C15 100.2(3) . . . . ?
S1 C11 N1 C8 -5.2(6) . . . . ?
S1 C11 N1 C10 -168.7(4) . . . . ?
C16 C17 C18 C19 -0.3(6) . . . . ?
C16 C21 C22 C23 -68.7(5) . . . . ?
C16 C21 C22 O2 55.5(5) . . . . ?
C17 C16 C21 C20 -0.3(6) . . . . ?
C17 C16 C21 C22 -179.6(4) . . . . ?
C17 C18 C19 C20 0.1(6) . . . . ?
C18 C19 C20 C21 0.0(6) . . . . ?
C19 C20 C21 C16 0.1(6) . . . . ?
C19 C20 C21 C22 179.4(4) . . . . ?
C20 C21 C22 C23 112.0(4) . . . . ?
C20 C21 C22 O2 -123.8(4) . . . . ?
C21 C16 C17 C18 0.4(6) . . . . ?
C21 C22 C23 C24 -68.2(4) . . . . ?
C21 C22 C23 N2 -168.0(3) . . . . ?
C22 C23 C24 C25 -107.6(3) . . . . ?
C22 C23 N2 C25 106.7(3) . . . . ?
C22 C23 N2 C26 -85.1(5) . . . . ?
C23 C24 C25 N2 -8.2(3) . . . . ?
C24 C23 N2 C25 -8.5(3) . . . . ?
C24 C23 N2 C26 159.6(4) . . . . ?
C24 C25 N2 C23 8.5(3) . . . . ?
C24 C25 N2 C26 -158.4(5) . . . . ?
C27 C26 N2 C23 -172.9(4) . . . . ?
C27 C26 N2 C25 -10.0(7) . . . . ?
N2 C23 C24 C25 8.3(3) . . . . ?
N2 C26 C27 C28 -163.6(4) . . . . ?
N2 C26 C27 C29 -44.0(5) . . . . ?
N2 C26 C27 C30 78.7(4) . . . . ?
O2 C22 C23 C24 170.3(3) . . . . ?
O2 C22 C23 N2 70.6(4) . . . . ?
S2 C26 C27 C28 18.2(5) . . . . ?
S2 C26 C27 C29 137.8(3) . . . . ?
S2 C26 C27 C30 -99.5(3) . . . . ?
S2 C26 N2 C23 5.3(6) . . . . ?
S2 C26 N2 C25 168.2(4) . . . . ?

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 0.0299 0.0039 -0.9990 0.0121 -0.0111 -0.0382 -0.0033
1 0 0 0.0962 0.9965 0.0188 -0.0252 -0.0749 0.0160 0.0647
-1 0 0 0.0962 -0.9965 -0.0188 0.0252 0.0749 -0.0160 -0.0647
0 0 1 0.0475 0.0007 -0.0003 1.0016 -0.0189 0.0072 -0.0240
0 0 -1 0.0475 -0.0007 0.0003 -1.0016 0.0189 -0.0072 0.0240
0 3 2 0.0368 -0.0102 2.9964 1.9668 -0.0047 0.1289 -0.0381
-1 6 0 0.0267 -1.0197 5.9751 -0.0474 0.1413 0.2130 -0.0450

_olex2_date_sample_data_collection 2012-12-19
_olex2_date_sample_submission    11/12/2012
_olex2_exptl_crystal_mounting_method 'oil on loop'
_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_pac1401
_database_code_depnum_ccdc_archive 'CCDC 1417068'
_audit_update_record             
;
2015-08-05 deposited with the CCDC.
2015-11-24 downloaded from the CCDC.
;
_audit_creation_date             2015-08-05
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_shelxl_version_number           2013-4
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C10 H17 N O2 S'
_chemical_formula_sum            'C10 H17 N O2 S'
_chemical_formula_weight         215.30
_chemical_absolute_configuration ad
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C10 H17 N1 O2 S1'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 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      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'

_cell_length_a                   6.51691(18)
_cell_length_b                   11.9691(3)
_cell_length_c                   29.6051(8)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2309.25(11)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    6616
_cell_measurement_temperature    110.00(14)
_cell_measurement_theta_max      31.7210
_cell_measurement_theta_min      3.2270
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.257
_exptl_absorpt_correction_T_max  0.988
_exptl_absorpt_correction_T_min  0.929
_exptl_absorpt_correction_type   gaussian
_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)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.239
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             928
_exptl_crystal_size_max          0.5506
_exptl_crystal_size_mid          0.0845
_exptl_crystal_size_min          0.0541
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0285
_diffrn_reflns_av_unetI/netI     0.0351
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       41
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_number            16952
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.214
_diffrn_reflns_theta_max         29.990
_diffrn_reflns_theta_min         3.197
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      110.00(14)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.1450
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega -102.00  -34.00   1.0000  100.0000
omega____ theta____ kappa____ phi______ frames
    -      -25.0740  178.0000   60.0000 68

#__ type_ start__ end____ width___ exp.time_
  2 omega   34.00  103.00   1.0000  100.0000
omega____ theta____ kappa____ phi______ frames
    -       26.4802 -178.0000   90.0000 69

#__ type_ start__ end____ width___ exp.time_
  3 omega  -18.00   99.00   1.0000  100.0000
omega____ theta____ kappa____ phi______ frames
    -       26.4802   19.0000 -120.0000 117

#__ type_ start__ end____ width___ exp.time_
  4 omega    6.00   61.00   1.0000  100.0000
omega____ theta____ kappa____ phi______ frames
    -       26.4802   57.0000  -30.0000 55
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Single source at offset, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0586619000
_diffrn_orient_matrix_UB_12      -0.0143532000
_diffrn_orient_matrix_UB_13      0.0193314000
_diffrn_orient_matrix_UB_21      0.0847316000
_diffrn_orient_matrix_UB_22      0.0132040000
_diffrn_orient_matrix_UB_23      0.0140463000
_diffrn_orient_matrix_UB_31      -0.0350241000
_diffrn_orient_matrix_UB_32      0.0559732000
_diffrn_orient_matrix_UB_33      0.0016441000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_reflns_Friedel_coverage         0.756
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.998
_reflns_number_gt                6219
_reflns_number_total             6729
_reflns_odcompleteness_completeness 99.79
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     29.97
_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 1.171.37.33 (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  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_refine_diff_density_max         0.269
_refine_diff_density_min         -0.190
_refine_diff_density_rms         0.043
_refine_ls_abs_structure_details 
;
 Flack x determined using 2491 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   0.06(2)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     267
_refine_ls_number_reflns         6729
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0397
_refine_ls_R_factor_gt           0.0352
_refine_ls_restrained_S_all      1.054
_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)+(0.0311P)²+0.5774P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0785
_refine_ls_wR_factor_ref         0.0807
_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:
 C2(H2), C12(H12)
2.b Secondary CH2 refined with riding coordinates:
 C3(H3A,H3B), C4(H4A,H4B), C5(H5A,H5B), C13(H13A,H13B), C14(H14A,H14B),
 C15(H15A,H15B)
2.c Idealised Me refined as rotating group:
 C8(H8A,H8B,H8C), C9(H9A,H9B,H9C), C10(H10A,H10B,H10C), C18(H18A,H18B,H18C),
 C19(H19A,H19B,H19C), C20(H20A,H20B,H20C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.4882(3) 0.3556(2) 0.27265(7) 0.0223(4) Uani 1 1 d . . . . .
C2 C 0.6508(3) 0.3710(2) 0.30913(7) 0.0264(5) Uani 1 1 d . . . . .
H2 H 0.6332 0.4431 0.3243 0.032 Uiso 1 1 calc R . . . .
C3 C 0.8653(4) 0.3628(3) 0.28800(8) 0.0433(7) Uani 1 1 d . . . . .
H3A H 0.8651 0.3905 0.2572 0.052 Uiso 1 1 calc R . . . .
H3B H 0.9651 0.4045 0.3055 0.052 Uiso 1 1 calc R . . . .
C4 C 0.9103(4) 0.2393(3) 0.28935(8) 0.0478(8) Uani 1 1 d . . . . .
H4A H 1.0564 0.2250 0.2869 0.057 Uiso 1 1 calc R . . . .
H4B H 0.8395 0.2001 0.2653 0.057 Uiso 1 1 calc R . . . .
C5 C 0.8288(3) 0.2046(2) 0.33544(7) 0.0280(5) Uani 1 1 d . . . . .
H5A H 0.7875 0.1267 0.3355 0.034 Uiso 1 1 calc R . . . .
H5B H 0.9311 0.2161 0.3588 0.034 Uiso 1 1 calc R . . . .
C6 C 0.4962(3) 0.27114(15) 0.37186(6) 0.0158(3) Uani 1 1 d . . . . .
C7 C 0.4979(3) 0.18084(17) 0.40913(7) 0.0204(4) Uani 1 1 d . . . . .
C8 C 0.7119(4) 0.15988(19) 0.42975(8) 0.0289(5) Uani 1 1 d . . . . .
H8A H 0.7883 0.1106 0.4105 0.043 Uiso 1 1 calc GR . . . .
H8B H 0.6969 0.1264 0.4590 0.043 Uiso 1 1 calc GR . . . .
H8C H 0.7836 0.2296 0.4326 0.043 Uiso 1 1 calc GR . . . .
C9 C 0.4117(4) 0.07305(18) 0.38834(9) 0.0299(5) Uani 1 1 d . . . . .
H9A H 0.2761 0.0868 0.3770 0.045 Uiso 1 1 calc GR . . . .
H9B H 0.4062 0.0158 0.4110 0.045 Uiso 1 1 calc GR . . . .
H9C H 0.4989 0.0492 0.3641 0.045 Uiso 1 1 calc GR . . . .
C10 C 0.3572(4) 0.2165(2) 0.44816(8) 0.0345(6) Uani 1 1 d . . . . .
H10A H 0.4058 0.2856 0.4607 0.052 Uiso 1 1 calc GR . . . .
H10B H 0.3580 0.1598 0.4711 0.052 Uiso 1 1 calc GR . . . .
H10C H 0.2200 0.2263 0.4371 0.052 Uiso 1 1 calc GR . . . .
N1 N 0.6492(3) 0.27947(15) 0.34217(5) 0.0198(3) Uani 1 1 d . . . . .
O1 O 0.4340(2) 0.26313(13) 0.25937(5) 0.0243(3) Uani 1 1 d . . . . .
O2 O 0.4307(3) 0.45003(14) 0.25468(6) 0.0332(4) Uani 1 1 d . . . . .
H2A H 0.349(6) 0.439(3) 0.2299(12) 0.069(11) Uiso 1 1 d . . . . .
S1 S 0.29561(8) 0.35780(4) 0.36701(2) 0.02238(11) Uani 1 1 d . . . . .
C11 C 0.1237(3) 0.32772(16) 0.17181(6) 0.0174(4) Uani 1 1 d . . . . .
C12 C -0.0425(3) 0.31865(16) 0.13606(6) 0.0184(4) Uani 1 1 d . . . . .
H12 H -0.0415 0.3853 0.1168 0.022 Uiso 1 1 calc R . . . .
C13 C -0.2536(3) 0.3058(2) 0.15893(8) 0.0264(4) Uani 1 1 d . . . . .
H13A H -0.2539 0.3399 0.1887 0.032 Uiso 1 1 calc R . . . .
H13B H -0.3609 0.3396 0.1408 0.032 Uiso 1 1 calc R . . . .
C14 C -0.2820(3) 0.17997(19) 0.16215(7) 0.0274(4) Uani 1 1 d . . . . .
H14A H -0.2062 0.1491 0.1874 0.033 Uiso 1 1 calc R . . . .
H14B H -0.4258 0.1604 0.1652 0.033 Uiso 1 1 calc R . . . .
C15 C -0.1960(3) 0.13997(17) 0.11769(7) 0.0222(4) Uani 1 1 d . . . . .
H15A H -0.1471 0.0637 0.1201 0.027 Uiso 1 1 calc R . . . .
H15B H -0.2990 0.1438 0.0941 0.027 Uiso 1 1 calc R . . . .
C16 C 0.1335(3) 0.20571(15) 0.07966(6) 0.0158(3) Uani 1 1 d . . . . .
C17 C 0.1527(3) 0.09928(16) 0.05054(7) 0.0185(4) Uani 1 1 d . . . . .
C18 C -0.0513(3) 0.06060(18) 0.02928(7) 0.0224(4) Uani 1 1 d . . . . .
H18A H -0.1282 0.0185 0.0511 0.034 Uiso 1 1 calc GR . . . .
H18B H -0.0233 0.0146 0.0035 0.034 Uiso 1 1 calc GR . . . .
H18C H -0.1294 0.1247 0.0201 0.034 Uiso 1 1 calc GR . . . .
C19 C 0.2414(4) 0.00683(18) 0.08069(8) 0.0293(5) Uani 1 1 d . . . . .
H19A H 0.3735 0.0295 0.0918 0.044 Uiso 1 1 calc GR . . . .
H19B H 0.2556 -0.0607 0.0634 0.044 Uiso 1 1 calc GR . . . .
H19C H 0.1508 -0.0061 0.1057 0.044 Uiso 1 1 calc GR . . . .
C20 C 0.3024(4) 0.11911(19) 0.01140(7) 0.0308(5) Uani 1 1 d . . . . .
H20A H 0.2484 0.1758 -0.0082 0.046 Uiso 1 1 calc GR . . . .
H20B H 0.3199 0.0510 -0.0053 0.046 Uiso 1 1 calc GR . . . .
H20C H 0.4325 0.1429 0.0232 0.046 Uiso 1 1 calc GR . . . .
N2 N -0.0243(3) 0.21755(13) 0.10817(5) 0.0161(3) Uani 1 1 d . . . . .
O3 O 0.1712(3) 0.42059(11) 0.18666(5) 0.0240(3) Uani 1 1 d . . . . .
O4 O 0.1905(2) 0.23358(11) 0.18815(5) 0.0189(3) Uani 1 1 d . . . . .
H4 H 0.269(5) 0.247(2) 0.2106(11) 0.049(9) Uiso 1 1 d . . . . .
S2 S 0.31446(9) 0.30491(4) 0.07850(2) 0.02351(12) Uani 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
C1 C2 1.524(3) . ?
C1 O1 1.227(3) . ?
C1 O2 1.304(3) . ?
C2 H2 0.9800 . ?
C2 C3 1.535(3) . ?
C2 N1 1.468(3) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C3 C4 1.508(5) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C4 C5 1.522(3) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C5 N1 1.488(3) . ?
C6 C7 1.545(3) . ?
C6 N1 1.333(2) . ?
C6 S1 1.6749(19) . ?
C7 C8 1.543(3) . ?
C7 C9 1.536(3) . ?
C7 C10 1.535(3) . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
O2 H2A 0.92(4) . ?
C11 C12 1.518(3) . ?
C11 O3 1.235(2) . ?
C11 O4 1.301(2) . ?
C12 H12 0.9800 . ?
C12 C13 1.541(3) . ?
C12 N2 1.470(2) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C13 C14 1.521(3) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C14 C15 1.509(3) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C15 N2 1.481(2) . ?
C16 C17 1.543(3) . ?
C16 N2 1.338(2) . ?
C16 S2 1.6740(19) . ?
C17 C18 1.542(3) . ?
C17 C19 1.535(3) . ?
C17 C20 1.533(3) . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
O4 H4 0.86(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 C1 C2 122.4(2) . . ?
O1 C1 O2 124.64(19) . . ?
O2 C1 C2 112.63(19) . . ?
C1 C2 H2 110.5 . . ?
C1 C2 C3 109.67(17) . . ?
C3 C2 H2 110.5 . . ?
N1 C2 C1 112.16(17) . . ?
N1 C2 H2 110.5 . . ?
N1 C2 C3 103.3(2) . . ?
C2 C3 H3A 111.1 . . ?
C2 C3 H3B 111.1 . . ?
H3A C3 H3B 109.1 . . ?
C4 C3 C2 103.2(2) . . ?
C4 C3 H3A 111.1 . . ?
C4 C3 H3B 111.1 . . ?
C3 C4 H4A 111.2 . . ?
C3 C4 H4B 111.2 . . ?
C3 C4 C5 102.9(2) . . ?
H4A C4 H4B 109.1 . . ?
C5 C4 H4A 111.2 . . ?
C5 C4 H4B 111.2 . . ?
C4 C5 H5A 111.1 . . ?
C4 C5 H5B 111.1 . . ?
H5A C5 H5B 109.1 . . ?
N1 C5 C4 103.3(2) . . ?
N1 C5 H5A 111.1 . . ?
N1 C5 H5B 111.1 . . ?
C7 C6 S1 120.02(14) . . ?
N1 C6 C7 121.19(17) . . ?
N1 C6 S1 118.74(15) . . ?
C8 C7 C6 113.77(16) . . ?
C9 C7 C6 107.38(17) . . ?
C9 C7 C8 110.65(18) . . ?
C10 C7 C6 109.80(17) . . ?
C10 C7 C8 106.69(18) . . ?
C10 C7 C9 108.44(19) . . ?
C7 C8 H8A 109.5 . . ?
C7 C8 H8B 109.5 . . ?
C7 C8 H8C 109.5 . . ?
H8A C8 H8B 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C7 C9 H9A 109.5 . . ?
C7 C9 H9B 109.5 . . ?
C7 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C7 C10 H10A 109.5 . . ?
C7 C10 H10B 109.5 . . ?
C7 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C2 N1 C5 110.77(17) . . ?
C6 N1 C2 120.03(18) . . ?
C6 N1 C5 129.17(17) . . ?
C1 O2 H2A 111(2) . . ?
O3 C11 C12 119.42(17) . . ?
O3 C11 O4 124.28(18) . . ?
O4 C11 C12 115.86(16) . . ?
C11 C12 H12 110.0 . . ?
C11 C12 C13 109.74(16) . . ?
C13 C12 H12 110.0 . . ?
N2 C12 C11 113.12(16) . . ?
N2 C12 H12 110.0 . . ?
N2 C12 C13 103.73(16) . . ?
C12 C13 H13A 111.0 . . ?
C12 C13 H13B 111.0 . . ?
H13A C13 H13B 109.0 . . ?
C14 C13 C12 103.59(17) . . ?
C14 C13 H13A 111.0 . . ?
C14 C13 H13B 111.0 . . ?
C13 C14 H14A 111.3 . . ?
C13 C14 H14B 111.3 . . ?
H14A C14 H14B 109.2 . . ?
C15 C14 C13 102.38(17) . . ?
C15 C14 H14A 111.3 . . ?
C15 C14 H14B 111.3 . . ?
C14 C15 H15A 110.9 . . ?
C14 C15 H15B 110.9 . . ?
H15A C15 H15B 108.9 . . ?
N2 C15 C14 104.36(16) . . ?
N2 C15 H15A 110.9 . . ?
N2 C15 H15B 110.9 . . ?
C17 C16 S2 121.11(14) . . ?
N2 C16 C17 120.16(16) . . ?
N2 C16 S2 118.64(14) . . ?
C18 C17 C16 113.94(16) . . ?
C19 C17 C16 107.50(16) . . ?
C19 C17 C18 110.23(17) . . ?
C20 C17 C16 110.26(16) . . ?
C20 C17 C18 106.65(17) . . ?
C20 C17 C19 108.16(18) . . ?
C17 C18 H18A 109.5 . . ?
C17 C18 H18B 109.5 . . ?
C17 C18 H18C 109.5 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C17 C19 H19A 109.5 . . ?
C17 C19 H19B 109.5 . . ?
C17 C19 H19C 109.5 . . ?
H19A C19 H19B 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C17 C20 H20A 109.5 . . ?
C17 C20 H20B 109.5 . . ?
C17 C20 H20C 109.5 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C12 N2 C15 110.36(16) . . ?
C16 N2 C12 120.26(16) . . ?
C16 N2 C15 129.38(16) . . ?
C11 O4 H4 109(2) . . ?

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
O2 H2A O3 0.92(4) 1.74(4) 2.653(2) 174(4) .
O4 H4 O1 0.86(3) 1.81(3) 2.662(2) 175(3) .

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C1 C2 C3 C4 -87.4(2) . . . . ?
C1 C2 N1 C5 106.5(2) . . . . ?
C1 C2 N1 C6 -71.8(2) . . . . ?
C2 C3 C4 C5 -40.9(2) . . . . ?
C3 C2 N1 C5 -11.5(2) . . . . ?
C3 C2 N1 C6 170.16(18) . . . . ?
C3 C4 C5 N1 33.4(2) . . . . ?
C4 C5 N1 C2 -13.5(2) . . . . ?
C4 C5 N1 C6 164.6(2) . . . . ?
C7 C6 N1 C2 -175.65(17) . . . . ?
C7 C6 N1 C5 6.4(3) . . . . ?
N1 C2 C3 C4 32.3(2) . . . . ?
N1 C6 C7 C8 38.6(3) . . . . ?
N1 C6 C7 C9 -84.2(2) . . . . ?
N1 C6 C7 C10 158.09(19) . . . . ?
O1 C1 C2 C3 82.3(3) . . . . ?
O1 C1 C2 N1 -31.9(3) . . . . ?
O2 C1 C2 C3 -91.4(3) . . . . ?
O2 C1 C2 N1 154.40(19) . . . . ?
S1 C6 C7 C8 -143.68(16) . . . . ?
S1 C6 C7 C9 93.52(19) . . . . ?
S1 C6 C7 C10 -24.2(2) . . . . ?
S1 C6 N1 C2 6.6(2) . . . . ?
S1 C6 N1 C5 -171.35(16) . . . . ?
C11 C12 C13 C14 -92.18(19) . . . . ?
C11 C12 N2 C15 111.39(18) . . . . ?
C11 C12 N2 C16 -67.9(2) . . . . ?
C12 C13 C14 C15 -39.4(2) . . . . ?
C13 C12 N2 C15 -7.4(2) . . . . ?
C13 C12 N2 C16 173.27(17) . . . . ?
C13 C14 C15 N2 34.7(2) . . . . ?
C14 C15 N2 C12 -17.2(2) . . . . ?
C14 C15 N2 C16 162.05(19) . . . . ?
C17 C16 N2 C12 179.78(16) . . . . ?
C17 C16 N2 C15 0.6(3) . . . . ?
N2 C12 C13 C14 29.0(2) . . . . ?
N2 C16 C17 C18 43.1(2) . . . . ?
N2 C16 C17 C19 -79.4(2) . . . . ?
N2 C16 C17 C20 162.95(18) . . . . ?
O3 C11 C12 C13 -89.4(2) . . . . ?
O3 C11 C12 N2 155.33(18) . . . . ?
O4 C11 C12 C13 83.4(2) . . . . ?
O4 C11 C12 N2 -31.9(2) . . . . ?
S2 C16 C17 C18 -140.33(15) . . . . ?
S2 C16 C17 C19 97.22(18) . . . . ?
S2 C16 C17 C20 -20.5(2) . . . . ?
S2 C16 N2 C12 3.1(2) . . . . ?
S2 C16 N2 C15 -176.03(16) . . . . ?

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 0 -1 0.0410 -0.0005 -0.0002 -0.9979 -0.0193 -0.0141 -0.0016
0 0 1 0.0330 0.0005 0.0002 0.9979 0.0193 0.0141 0.0016
0 1 -1 0.0315 -0.0002 0.9979 -0.9971 -0.0336 -0.0008 0.0542
0 -1 1 0.0225 0.0002 -0.9979 0.9971 0.0336 0.0008 -0.0542
2 1 1 0.2578 1.9985 0.9948 0.9847 -0.1125 0.1963 -0.0127
-4 -5 -3 0.2047 -3.9985 -4.9843 -2.9697 0.2487 -0.4463 -0.1438
0 2 1 0.0317 0.0012 1.9965 0.9995 -0.0094 0.0405 0.1134
0 -2 -1 0.0247 -0.0012 -1.9965 -0.9995 0.0094 -0.0405 -0.1134

_olex2_date_sample_data_collection 2014-04-28
_olex2_submission_special_instructions 'No special instructions were received'
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Ethyl acetate/pentane'
####################################################################### 
# 
# 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_pac1403
_database_code_depnum_ccdc_archive 'CCDC 1417069'
_audit_update_record             
;
2015-08-05 deposited with the CCDC.
2015-11-24 downloaded from the CCDC.
;
_audit_creation_date             2014-05-13
_audit_creation_method           
;
Olex2 1.2
(compiled 2014.03.20 svn.r2914 for OlexSys, GUI svn.r4816)
;
_shelxl_version_number           2013-4
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C9 H15 N O2 S'
_chemical_formula_sum            'C9 H15 N O2 S'
_chemical_formula_weight         201.28
_chemical_absolute_configuration ad
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C9 H15 N1 O2 S1'
_chemical_oxdiff_usercomment     'Joshua Smith 3-69-1-F'
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           4
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   9.6985(3)
_cell_length_b                   6.50545(16)
_cell_length_c                   17.1860(5)
_cell_angle_alpha                90
_cell_angle_beta                 94.266(2)
_cell_angle_gamma                90
_cell_volume                     1081.31(5)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3995
_cell_measurement_temperature    110.05(10)
_cell_measurement_theta_max      31.8520
_cell_measurement_theta_min      3.5710
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.270
_exptl_absorpt_correction_T_max  0.986
_exptl_absorpt_correction_T_min  0.950
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.236
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plank
_exptl_crystal_F_000             432
_exptl_crystal_size_max          0.2111
_exptl_crystal_size_mid          0.1102
_exptl_crystal_size_min          0.0427
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0294
_diffrn_reflns_av_unetI/netI     0.0447
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            10292
_diffrn_reflns_point_group_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.963
_diffrn_reflns_theta_full        25.214
_diffrn_reflns_theta_max         29.992
_diffrn_reflns_theta_min         3.053
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      110.05(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.1450
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Single source at offset, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0326108000
_diffrn_orient_matrix_UB_12      -0.0095958000
_diffrn_orient_matrix_UB_13      -0.0354321000
_diffrn_orient_matrix_UB_21      -0.0655598000
_diffrn_orient_matrix_UB_22      -0.0113799000
_diffrn_orient_matrix_UB_23      -0.0207067000
_diffrn_orient_matrix_UB_31      -0.0038697000
_diffrn_orient_matrix_UB_32      0.1080384000
_diffrn_orient_matrix_UB_33      -0.0053068000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_diffrn_special_details          ?
_reflns_Friedel_coverage         0.786
_reflns_Friedel_fraction_full    0.982
_reflns_Friedel_fraction_max     0.923
_reflns_number_gt                5582
_reflns_number_total             6093
_reflns_odcompleteness_completeness 99.71
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     29.97
_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 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_refine_diff_density_max         0.532
_refine_diff_density_min         -0.249
_refine_diff_density_rms         0.059
_refine_ls_abs_structure_details 
;
 Flack x determined using 2296 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   -0.02(4)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.072
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     245
_refine_ls_number_reflns         6093
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0470
_refine_ls_R_factor_gt           0.0415
_refine_ls_restrained_S_all      1.072
_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)+(0.0556P)²+0.0836P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1003
_refine_ls_wR_factor_ref         0.1047
_refine_special_details          
;
The diffraction pattern revealed the presence of a very minor non-merohedral
 twin.  This was not included in the model as inclusion lead to a significant 
reduction in the quality of the final structure.
;
_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, All O(H) groups
2.a Riding coordinates:
 O2(H2A)
2.b Ternary CH refined with riding coordinates:
 C2(H2), C11(H11)
2.c Secondary CH2 refined with riding coordinates:
 C3(H3A,H3B), C4(H4A,H4B), C12(H12A,H12B), C13(H13A,H13B)
2.d Idealised Me refined as rotating group:
 C7(H7A,H7B,H7C), C8(H8A,H8B,H8C), C9(H9A,H9B,H9C), C16(H16A,H16B,H16C),
 C17(H17A,H17B,H17C), C18(H18A,H18B,H18C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.3282(3) 0.2447(4) 0.68278(14) 0.0190(5) Uani 1 1 d . . . . .
C2 C 0.3914(2) 0.4029(4) 0.63183(13) 0.0181(4) Uani 1 1 d . . . . .
H2 H 0.4885 0.3760 0.6231 0.022 Uiso 1 1 calc R . . . .
C3 C 0.3629(3) 0.6276(4) 0.65725(14) 0.0234(5) Uani 1 1 d . . . . .
H3A H 0.3227 0.6382 0.7071 0.028 Uiso 1 1 calc R . . . .
H3B H 0.4416 0.7188 0.6550 0.028 Uiso 1 1 calc R . . . .
C4 C 0.2568(3) 0.6447(4) 0.58631(16) 0.0241(5) Uani 1 1 d . . . . .
H4A H 0.1614 0.6466 0.5997 0.029 Uiso 1 1 calc R . . . .
H4B H 0.2750 0.7564 0.5511 0.029 Uiso 1 1 calc R . . . .
C5 C 0.2933(2) 0.3217(4) 0.49728(14) 0.0170(4) Uani 1 1 d . . . . .
C6 C 0.2008(2) 0.3910(4) 0.42595(14) 0.0186(4) Uani 1 1 d . . . . .
C7 C 0.0671(3) 0.4908(4) 0.44933(16) 0.0267(6) Uani 1 1 d . . . . .
H7A H 0.0299 0.4113 0.4899 0.040 Uiso 1 1 calc GR . . . .
H7B H 0.0011 0.4960 0.4049 0.040 Uiso 1 1 calc GR . . . .
H7C H 0.0864 0.6278 0.4679 0.040 Uiso 1 1 calc GR . . . .
C8 C 0.1627(3) 0.2069(4) 0.37334(16) 0.0270(6) Uani 1 1 d . . . . .
H8A H 0.1163 0.1053 0.4024 0.041 Uiso 1 1 calc GR . . . .
H8B H 0.2452 0.1486 0.3550 0.041 Uiso 1 1 calc GR . . . .
H8C H 0.1027 0.2512 0.3296 0.041 Uiso 1 1 calc GR . . . .
C9 C 0.2810(3) 0.5477(5) 0.38002(15) 0.0259(5) Uani 1 1 d . . . . .
H9A H 0.2258 0.5881 0.3339 0.039 Uiso 1 1 calc GR . . . .
H9B H 0.3655 0.4867 0.3655 0.039 Uiso 1 1 calc GR . . . .
H9C H 0.3019 0.6664 0.4120 0.039 Uiso 1 1 calc GR . . . .
N1 N 0.3043(2) 0.4407(3) 0.56018(12) 0.0175(4) Uani 1 1 d . . . . .
O1 O 0.20478(19) 0.2041(3) 0.67491(11) 0.0254(4) Uani 1 1 d . . . . .
O2 O 0.4143(2) 0.1706(3) 0.73720(11) 0.0308(5) Uani 1 1 d . . . . .
H2A H 0.3738 0.0927 0.7621 0.046 Uiso 1 1 d R . . . .
S1 S 0.38604(6) 0.10519(10) 0.49967(3) 0.02153(14) Uani 1 1 d . . . . .
C10 C -0.1597(3) 0.3729(4) 0.18048(14) 0.0217(5) Uani 1 1 d . . . . .
C11 C -0.0998(3) 0.2077(4) 0.13178(15) 0.0232(5) Uani 1 1 d . . . . .
H11 H -0.1411 0.2082 0.0780 0.028 Uiso 1 1 calc R . . . .
C12 C -0.1000(3) -0.0111(4) 0.16877(19) 0.0349(7) Uani 1 1 d . . . . .
H12A H -0.1360 -0.0150 0.2199 0.042 Uiso 1 1 calc R . . . .
H12B H -0.1433 -0.1151 0.1347 0.042 Uiso 1 1 calc R . . . .
C13 C 0.0589(3) -0.0104(4) 0.17106(17) 0.0293(6) Uani 1 1 d . . . . .
H13A H 0.1041 -0.0128 0.2234 0.035 Uiso 1 1 calc R . . . .
H13B H 0.0969 -0.1147 0.1384 0.035 Uiso 1 1 calc R . . . .
C14 C 0.1330(3) 0.3248(4) 0.09932(14) 0.0209(5) Uani 1 1 d . . . . .
C15 C 0.2876(3) 0.2751(5) 0.09930(16) 0.0284(6) Uani 1 1 d . . . . .
C16 C 0.3495(3) 0.2094(7) 0.17977(19) 0.0477(9) Uani 1 1 d . . . . .
H16A H 0.4484 0.2058 0.1798 0.072 Uiso 1 1 calc GR . . . .
H16B H 0.3158 0.0752 0.1918 0.072 Uiso 1 1 calc GR . . . .
H16C H 0.3230 0.3059 0.2182 0.072 Uiso 1 1 calc GR . . . .
C17 C 0.3692(4) 0.4618(8) 0.0746(3) 0.0608(12) Uani 1 1 d . . . . .
H17A H 0.3626 0.5699 0.1121 0.091 Uiso 1 1 calc GR . . . .
H17B H 0.3319 0.5085 0.0243 0.091 Uiso 1 1 calc GR . . . .
H17C H 0.4644 0.4244 0.0716 0.091 Uiso 1 1 calc GR . . . .
C18 C 0.3043(3) 0.1009(8) 0.0406(2) 0.0578(12) Uani 1 1 d . . . . .
H18A H 0.2660 0.1429 -0.0100 0.087 Uiso 1 1 calc GR . . . .
H18B H 0.2566 -0.0192 0.0569 0.087 Uiso 1 1 calc GR . . . .
H18C H 0.4007 0.0700 0.0383 0.087 Uiso 1 1 calc GR . . . .
N2 N 0.0511(2) 0.1969(3) 0.13517(12) 0.0218(4) Uani 1 1 d . . . . .
O3 O -0.2813(2) 0.4223(3) 0.16811(11) 0.0275(4) Uani 1 1 d . . . . .
O4 O -0.0780(2) 0.4441(3) 0.23743(11) 0.0278(4) Uani 1 1 d . . . . .
S2 S 0.05927(7) 0.52959(11) 0.05550(4) 0.02502(15) Uani 1 1 d . . . . .
H4 H -0.117(5) 0.529(8) 0.263(3) 0.070(15) 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
C1 C2 1.510(3) . ?
C1 O1 1.224(3) . ?
C1 O2 1.299(3) . ?
C2 H2 0.9800 . ?
C2 C3 1.557(4) . ?
C2 N1 1.462(3) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C3 C4 1.540(4) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C4 N1 1.486(3) . ?
C5 C6 1.532(3) . ?
C5 N1 1.327(3) . ?
C5 S1 1.670(2) . ?
C6 C7 1.531(3) . ?
C6 C8 1.529(4) . ?
C6 C9 1.536(3) . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
O2 H2A 0.7867 . ?
C10 C11 1.505(3) . ?
C10 O3 1.226(3) . ?
C10 O4 1.298(3) . ?
C11 H11 0.9800 . ?
C11 C12 1.559(4) . ?
C11 N2 1.462(3) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C12 C13 1.539(5) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C13 N2 1.483(3) . ?
C14 C15 1.534(4) . ?
C14 N2 1.332(3) . ?
C14 S2 1.665(3) . ?
C15 C16 1.527(4) . ?
C15 C17 1.527(5) . ?
C15 C18 1.533(5) . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
O4 H4 0.82(5) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 C1 C2 121.3(2) . . ?
O1 C1 O2 124.8(2) . . ?
O2 C1 C2 113.8(2) . . ?
C1 C2 H2 113.8 . . ?
C1 C2 C3 112.88(18) . . ?
C3 C2 H2 113.8 . . ?
N1 C2 C1 111.6(2) . . ?
N1 C2 H2 113.8 . . ?
N1 C2 C3 88.54(19) . . ?
C2 C3 H3A 114.0 . . ?
C2 C3 H3B 114.0 . . ?
H3A C3 H3B 111.2 . . ?
C4 C3 C2 88.18(18) . . ?
C4 C3 H3A 114.0 . . ?
C4 C3 H3B 114.0 . . ?
C3 C4 H4A 113.9 . . ?
C3 C4 H4B 113.9 . . ?
H4A C4 H4B 111.1 . . ?
N1 C4 C3 88.31(19) . . ?
N1 C4 H4A 113.9 . . ?
N1 C4 H4B 113.9 . . ?
C6 C5 S1 123.37(18) . . ?
N1 C5 C6 119.1(2) . . ?
N1 C5 S1 117.49(19) . . ?
C5 C6 C9 108.5(2) . . ?
C7 C6 C5 111.8(2) . . ?
C7 C6 C9 108.9(2) . . ?
C8 C6 C5 110.1(2) . . ?
C8 C6 C7 108.4(2) . . ?
C8 C6 C9 109.0(2) . . ?
C6 C7 H7A 109.5 . . ?
C6 C7 H7B 109.5 . . ?
C6 C7 H7C 109.5 . . ?
H7A C7 H7B 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C6 C8 H8A 109.5 . . ?
C6 C8 H8B 109.5 . . ?
C6 C8 H8C 109.5 . . ?
H8A C8 H8B 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C6 C9 H9A 109.5 . . ?
C6 C9 H9B 109.5 . . ?
C6 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C2 N1 C4 93.94(19) . . ?
C5 N1 C2 126.5(2) . . ?
C5 N1 C4 139.4(2) . . ?
C1 O2 H2A 108.1 . . ?
O3 C10 C11 119.8(2) . . ?
O3 C10 O4 124.2(2) . . ?
O4 C10 C11 115.8(2) . . ?
C10 C11 H11 112.0 . . ?
C10 C11 C12 114.4(2) . . ?
C12 C11 H11 112.0 . . ?
N2 C11 C10 116.0(2) . . ?
N2 C11 H11 112.0 . . ?
N2 C11 C12 88.4(2) . . ?
C11 C12 H12A 113.9 . . ?
C11 C12 H12B 113.9 . . ?
H12A C12 H12B 111.1 . . ?
C13 C12 C11 88.6(2) . . ?
C13 C12 H12A 113.9 . . ?
C13 C12 H12B 113.9 . . ?
C12 C13 H13A 113.9 . . ?
C12 C13 H13B 113.9 . . ?
H13A C13 H13B 111.1 . . ?
N2 C13 C12 88.4(2) . . ?
N2 C13 H13A 113.9 . . ?
N2 C13 H13B 113.9 . . ?
C15 C14 S2 123.7(2) . . ?
N2 C14 C15 119.0(2) . . ?
N2 C14 S2 117.2(2) . . ?
C16 C15 C14 112.1(2) . . ?
C16 C15 C17 107.3(3) . . ?
C16 C15 C18 109.6(3) . . ?
C17 C15 C14 111.0(3) . . ?
C17 C15 C18 108.8(3) . . ?
C18 C15 C14 107.9(2) . . ?
C15 C16 H16A 109.5 . . ?
C15 C16 H16B 109.5 . . ?
C15 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C15 C17 H17A 109.5 . . ?
C15 C17 H17B 109.5 . . ?
C15 C17 H17C 109.5 . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C15 C18 H18A 109.5 . . ?
C15 C18 H18B 109.5 . . ?
C15 C18 H18C 109.5 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C11 N2 C13 94.6(2) . . ?
C14 N2 C11 125.5(2) . . ?
C14 N2 C13 138.3(2) . . ?
C10 O4 H4 111(3) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C1 C2 C3 C4 -105.4(2) . . . . ?
C1 C2 N1 C4 106.3(2) . . . . ?
C1 C2 N1 C5 -78.0(3) . . . . ?
C2 C3 C4 N1 -7.42(16) . . . . ?
C3 C2 N1 C4 -7.83(17) . . . . ?
C3 C2 N1 C5 167.9(2) . . . . ?
C3 C4 N1 C2 7.91(18) . . . . ?
C3 C4 N1 C5 -166.8(3) . . . . ?
C6 C5 N1 C2 -177.5(2) . . . . ?
C6 C5 N1 C4 -4.0(4) . . . . ?
N1 C2 C3 C4 7.54(17) . . . . ?
N1 C5 C6 C7 -39.6(3) . . . . ?
N1 C5 C6 C8 -160.2(2) . . . . ?
N1 C5 C6 C9 80.5(3) . . . . ?
O1 C1 C2 C3 78.2(3) . . . . ?
O1 C1 C2 N1 -19.7(3) . . . . ?
O2 C1 C2 C3 -97.4(3) . . . . ?
O2 C1 C2 N1 164.7(2) . . . . ?
S1 C5 C6 C7 142.15(19) . . . . ?
S1 C5 C6 C8 21.6(3) . . . . ?
S1 C5 C6 C9 -97.7(2) . . . . ?
S1 C5 N1 C2 0.9(3) . . . . ?
S1 C5 N1 C4 174.3(2) . . . . ?
C10 C11 C12 C13 -117.5(2) . . . . ?
C10 C11 N2 C13 116.0(2) . . . . ?
C10 C11 N2 C14 -76.1(3) . . . . ?
C11 C12 C13 N2 -0.4(2) . . . . ?
C12 C11 N2 C13 -0.5(2) . . . . ?
C12 C11 N2 C14 167.4(2) . . . . ?
C12 C13 N2 C11 0.5(2) . . . . ?
C12 C13 N2 C14 -164.6(3) . . . . ?
C15 C14 N2 C11 -171.5(2) . . . . ?
C15 C14 N2 C13 -9.9(5) . . . . ?
N2 C11 C12 C13 0.4(2) . . . . ?
N2 C14 C15 C16 -45.4(4) . . . . ?
N2 C14 C15 C17 -165.5(3) . . . . ?
N2 C14 C15 C18 75.4(3) . . . . ?
O3 C10 C11 C12 -95.4(3) . . . . ?
O3 C10 C11 N2 163.8(2) . . . . ?
O4 C10 C11 C12 80.0(3) . . . . ?
O4 C10 C11 N2 -20.7(3) . . . . ?
S2 C14 C15 C16 135.6(3) . . . . ?
S2 C14 C15 C17 15.5(4) . . . . ?
S2 C14 C15 C18 -103.6(3) . . . . ?
S2 C14 N2 C11 7.5(3) . . . . ?
S2 C14 N2 C13 169.2(3) . . . . ?

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
-5 0 -4 0.0214 -4.8098 0.3173 -3.6828 -0.0294 0.3880 0.0724
5 0 4 0.0214 4.8098 -0.3173 3.6828 0.0294 -0.3880 -0.0724
0 -1 0 0.1080 -0.1308 -0.9985 -0.0240 0.0062 0.0204 -0.1072
1 1 0 0.0894 1.1182 0.9370 0.1583 0.0219 -0.0873 0.0961
1 0 -5 0.0803 1.1991 -0.0457 -4.8843 0.2126 0.0230 0.0163
-1 0 5 0.0299 -1.1991 0.0457 4.8843 -0.2126 -0.0230 -0.0163
0 1 0 0.1030 0.1308 0.9985 0.0240 -0.0062 -0.0204 0.1072

#===end

# start Validation Reply Form
_vrf_DIFMX01_pac1202             
;
PROBLEM: The maximum difference density is > 0.1*ZMAX*1.00
RESPONSE: The larger than expected residual densities are believed to be due to 
non-merohedral twinning which could not be resolved.
;
_vrf_PLAT094_pac1202             
;
PROBLEM: Ratio of Maximum / Minimum Residual Density .... 5.98 Report
RESPONSE: The larger than expected residual densities are believed to be due to 
non-merohedral twinning which could not be resolved.
;
# end Validation Reply Form_exptl_crystal_recrystallization_method 
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Ethyl acetate/pentane'
