# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2014

#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_1c
_audit_creation_date             2014-09-26
_audit_creation_method           
;
Olex2 1.2
(compiled 2014.09.19 svn.r3010 for OlexSys, GUI svn.r4874)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C16 H28 N2 O S'
_chemical_formula_sum            'C16 H28 N2 O S'
_chemical_formula_weight         296.46
_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'
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/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, y+1/2, -z+1/2'
3 '-x, -y, -z'
4 'x, -y-1/2, z-1/2'

_cell_length_a                   20.6963(8)
_cell_length_b                   4.89894(19)
_cell_length_c                   16.9658(7)
_cell_angle_alpha                90.00
_cell_angle_beta                 97.371(4)
_cell_angle_gamma                90.00
_cell_volume                     1705.95(12)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2546
_cell_measurement_temperature    298
_cell_measurement_theta_max      27.1970
_cell_measurement_theta_min      3.5880
_exptl_absorpt_coefficient_mu    0.189
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.65473
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.154
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             648
_exptl_crystal_size_max          0.9
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.15
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0214
_diffrn_reflns_av_unetI/netI     0.0281
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_k_max       3
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            6661
_diffrn_reflns_theta_full        27.32
_diffrn_reflns_theta_max         27.32
_diffrn_reflns_theta_min         3.32
_diffrn_ambient_temperature      298
_diffrn_detector_area_resol_mean 16.1702
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -81.00   71.00   1.0000    7.5200
omega____ theta____ kappa____ phi______ frames
    -       16.6632  -38.0000 -180.0000 152

#__ type_ start__ end____ width___ exp.time_
  2 omega  -19.00    8.00   1.0000    7.5200
omega____ theta____ kappa____ phi______ frames
    -       16.6632  -99.0000  120.0000 27

#__ type_ start__ end____ width___ exp.time_
  3 omega  -66.00   -7.00   1.0000   30.0600
omega____ theta____ kappa____ phi______ frames
    -       35.8427  -45.0000 -120.0000 59

#__ type_ start__ end____ width___ exp.time_
  4 omega  -34.00   53.00   1.0000   30.0600
omega____ theta____ kappa____ phi______ frames
    -       35.8427  -30.0000   60.0000 87

#__ type_ start__ end____ width___ exp.time_
  5 omega    9.00   75.00   1.0000   30.0600
omega____ theta____ kappa____ phi______ frames
    -       35.8427  -45.0000 -120.0000 66

#__ type_ start__ end____ width___ exp.time_
  6 omega   27.00   80.00   1.0000   30.0600
omega____ theta____ kappa____ phi______ frames
    -       35.8427 -125.0000  -90.0000 53

#__ type_ start__ end____ width___ exp.time_
  7 omega -142.00 -101.00   1.0000   30.0600
omega____ theta____ kappa____ phi______ frames
    -      -35.9989  -95.0000  150.0000 41

#__ type_ start__ end____ width___ exp.time_
  8 omega  -68.00    6.00   1.0000   30.0600
omega____ theta____ kappa____ phi______ frames
    -      -35.9989   30.0000  -90.0000 74
;
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0213242000
_diffrn_orient_matrix_UB_12      -0.0196782000
_diffrn_orient_matrix_UB_13      0.0290545000
_diffrn_orient_matrix_UB_21      -0.0271229000
_diffrn_orient_matrix_UB_22      0.0253020000
_diffrn_orient_matrix_UB_23      -0.0291094000
_diffrn_orient_matrix_UB_31      -0.0018580000
_diffrn_orient_matrix_UB_32      -0.1412088000
_diffrn_orient_matrix_UB_33      -0.0092693000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                3034
_reflns_number_total             3611
_reflns_odcompleteness_completeness 99.57
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_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         0.251
_refine_diff_density_min         -0.258
_refine_diff_density_rms         0.044
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.067
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     186
_refine_ls_number_reflns         3611
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0541
_refine_ls_R_factor_gt           0.0445
_refine_ls_restrained_S_all      1.067
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0700P)²+0.2970P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1231
_refine_ls_wR_factor_ref         0.1339
_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:
  All C(H) groups, All C(H,H) groups, All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B), C9(H9A,H9B), C10(H10A,H10B), C12(H12A,H12B), C13(H13A,H13B),
 C11(H11A,H11B), C14(H14A,H14B), C17(H17A,H17B), C15(H15A,H15B), C16(H16A,H16B),
  C18(H18A,H18B)
2.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4)
2.c Idealised Me refined as rotating group:
 C19(H19A,H19B,H19C)
;
_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_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_refinement_flags_posn
S5 S 0.45650(2) -0.07837(9) 0.34922(2) 0.04749(16) Uani 1 d . . .
O20 O 0.34690(6) -0.0238(3) 0.41972(8) 0.0574(3) Uani 1 d . . .
N6 N 0.42560(6) 0.2811(3) 0.46200(8) 0.0402(3) Uani 1 d . . .
N2 N 0.52969(6) 0.2872(3) 0.42358(8) 0.0433(3) Uani 1 d . . .
C1 C 0.47129(7) 0.1826(3) 0.41740(8) 0.0367(3) Uani 1 d . . .
C7 C 0.36394(7) 0.1762(3) 0.45948(9) 0.0403(3) Uani 1 d . . .
C8 C 0.32043(7) 0.3317(3) 0.50780(10) 0.0458(4) Uani 1 d . . .
H8A H 0.3122 0.5111 0.4844 0.055 Uiso 1 calc . . R
H8B H 0.3430 0.3568 0.5611 0.055 Uiso 1 calc . . R
C9 C 0.25576(7) 0.1929(4) 0.51333(11) 0.0474(4) Uani 1 d . . .
H9A H 0.2634 0.0273 0.5444 0.057 Uiso 1 calc . . R
H9B H 0.2363 0.1412 0.4604 0.057 Uiso 1 calc . . R
C10 C 0.20830(7) 0.3719(3) 0.55079(10) 0.0458(4) Uani 1 d . . .
H10A H 0.2004 0.5365 0.5193 0.055 Uiso 1 calc . . R
H10B H 0.2281 0.4255 0.6034 0.055 Uiso 1 calc . . R
C3 C 0.56513(8) 0.1590(4) 0.37077(10) 0.0474(4) Uani 1 d . . .
H3 H 0.6079 0.2074 0.3661 0.057 Uiso 1 calc . . R
C12 C 0.09551(8) 0.4125(4) 0.59413(11) 0.0489(4) Uani 1 d . . .
H12A H 0.0877 0.5762 0.5622 0.059 Uiso 1 calc . . R
H12B H 0.1150 0.4679 0.6467 0.059 Uiso 1 calc . . R
C4 C 0.53437(8) -0.0385(4) 0.32679(10) 0.0504(4) Uani 1 d . . .
H4 H 0.5527 -0.1407 0.2891 0.060 Uiso 1 calc . . R
C13 C 0.03069(7) 0.2762(4) 0.60100(11) 0.0502(4) Uani 1 d . . .
H13A H 0.0110 0.2215 0.5484 0.060 Uiso 1 calc . . R
H13B H 0.0385 0.1122 0.6328 0.060 Uiso 1 calc . . R
C11 C 0.14356(8) 0.2341(4) 0.55761(11) 0.0499(4) Uani 1 d . . .
H11A H 0.1241 0.1785 0.5050 0.060 Uiso 1 calc . . R
H11B H 0.1515 0.0705 0.5896 0.060 Uiso 1 calc . . R
C14 C -0.01682(8) 0.4560(4) 0.63786(11) 0.0546(5) Uani 1 d . . .
H14A H 0.0033 0.5119 0.6902 0.065 Uiso 1 calc . . R
H14B H -0.0246 0.6194 0.6058 0.065 Uiso 1 calc . . R
C17 C -0.19274(8) 0.3860(4) 0.69423(12) 0.0578(5) Uani 1 d . . .
H17A H -0.1843 0.2341 0.7308 0.069 Uiso 1 calc . . R
H17B H -0.2138 0.3140 0.6442 0.069 Uiso 1 calc . . R
C15 C -0.08171(8) 0.3245(4) 0.64603(11) 0.0521(4) Uani 1 d . . .
H15A H -0.0743 0.1644 0.6796 0.063 Uiso 1 calc . . R
H15B H -0.1015 0.2641 0.5940 0.063 Uiso 1 calc . . R
C16 C -0.12870(9) 0.5125(4) 0.68087(12) 0.0592(5) Uani 1 d . . .
H16A H -0.1076 0.5811 0.7313 0.071 Uiso 1 calc . . R
H16B H -0.1375 0.6678 0.6456 0.071 Uiso 1 calc . . R
C18 C -0.23869(10) 0.5826(5) 0.72717(14) 0.0722(6) Uani 1 d . . .
H18A H -0.2163 0.6643 0.7752 0.087 Uiso 1 calc . . R
H18B H -0.2492 0.7280 0.6889 0.087 Uiso 1 calc . . R
C19 C -0.30053(11) 0.4590(6) 0.74610(16) 0.0930(8) Uani 1 d . . .
H19A H -0.3241 0.3837 0.6986 0.112 Uiso 1 calc . . GR
H19B H -0.3266 0.5967 0.7671 0.112 Uiso 1 calc . . GR
H19C H -0.2909 0.3169 0.7848 0.112 Uiso 1 calc . . GR
H6 H 0.4355(9) 0.416(4) 0.4967(11) 0.054(5) Uiso 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
S5 C1 1.7250(15) . ?
S5 C4 1.7139(17) . ?
O20 C7 1.2159(19) . ?
N6 C1 1.3721(18) . ?
N6 C7 1.3713(18) . ?
N2 C1 1.3045(18) . ?
N2 C3 1.380(2) . ?
C7 C8 1.501(2) . ?
C8 C9 1.515(2) . ?
C9 C10 1.516(2) . ?
C10 C11 1.518(2) . ?
C3 C4 1.333(2) . ?
C12 C13 1.516(2) . ?
C12 C11 1.515(2) . ?
C13 C14 1.514(2) . ?
C14 C15 1.512(2) . ?
C17 C16 1.506(2) . ?
C17 C18 1.510(3) . ?
C15 C16 1.514(2) . ?
C18 C19 1.488(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
C4 S5 C1 88.48(7) . . ?
C7 N6 C1 123.75(14) . . ?
C1 N2 C3 109.46(14) . . ?
N6 C1 S5 123.70(11) . . ?
N2 C1 S5 115.33(11) . . ?
N2 C1 N6 120.96(14) . . ?
O20 C7 N6 121.45(14) . . ?
O20 C7 C8 124.08(14) . . ?
N6 C7 C8 114.46(14) . . ?
C7 C8 C9 113.76(14) . . ?
C8 C9 C10 113.06(14) . . ?
C9 C10 C11 113.63(14) . . ?
C4 C3 N2 116.01(15) . . ?
C11 C12 C13 114.28(15) . . ?
C3 C4 S5 110.71(12) . . ?
C14 C13 C12 113.80(15) . . ?
C12 C11 C10 114.02(15) . . ?
C15 C14 C13 114.95(15) . . ?
C16 C17 C18 113.66(17) . . ?
C14 C15 C16 113.54(16) . . ?
C17 C16 C15 115.48(17) . . ?
C19 C18 C17 114.9(2) . . ?

_database_code_depnum_ccdc_archive 'CCDC 958233'
_olex2_submission_special_instructions 'No special instructions were received'

_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: '
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_1d
_audit_creation_date             2014-09-26
_audit_creation_method           
;
Olex2 1.2
(compiled 2014.09.19 svn.r3010 for OlexSys, GUI svn.r4874)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C17 H30 N2 O S'
_chemical_formula_sum            'C17 H30 N2 O S'
_chemical_formula_weight         310.49
_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 0.0181 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'

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

_cell_length_a                   23.237(2)
_cell_length_b                   4.9497(3)
_cell_length_c                   15.6429(12)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.966(8)
_cell_angle_gamma                90.00
_cell_volume                     1798.9(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1165
_cell_measurement_temperature    298
_cell_measurement_theta_max      71.6100
_cell_measurement_theta_min      3.7750
_exptl_absorpt_coefficient_mu    1.594
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.43399
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_lustre     ?
_exptl_crystal_colour_modifier   ?
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.146
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             680
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.02
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0754
_diffrn_reflns_av_unetI/netI     0.1325
_diffrn_reflns_limit_h_max       28
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       3
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            6473
_diffrn_reflns_theta_full        72.06
_diffrn_reflns_theta_max         72.06
_diffrn_reflns_theta_min         3.81
_diffrn_ambient_temperature      298
_diffrn_detector_area_resol_mean 8.0851
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -18.00    7.00   1.0000   23.9500
omega____ theta____ kappa____ phi______ frames
    -        0.0000   57.0000  -90.0000 25

#__ type_ start__ end____ width___ exp.time_
  2 omega   44.00   69.00   1.0000   23.9500
omega____ theta____ kappa____ phi______ frames
    -        0.0000   57.0000  -90.0000 25

#__ type_ start__ end____ width___ exp.time_
  3 omega -104.00  -21.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      -42.5000  -50.0000   60.0000 83

#__ type_ start__ end____ width___ exp.time_
  4 omega  -45.00   -2.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      -42.5000   25.0000   90.0000 43

#__ type_ start__ end____ width___ exp.time_
  5 omega  -90.00  -38.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      -42.5000  111.0000    0.0000 52

#__ type_ start__ end____ width___ exp.time_
  6 omega  -89.00  -22.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      -42.5000  -50.0000  -60.0000 67

#__ type_ start__ end____ width___ exp.time_
  7 omega   68.00  124.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       54.7151   57.0000   90.0000 56

#__ type_ start__ end____ width___ exp.time_
  8 omega   44.00   72.00   1.0000   51.0000
omega____ theta____ kappa____ phi______ frames
    -      109.4303 -111.0000   30.0000 28

#__ type_ start__ end____ width___ exp.time_
  9 omega   37.00   86.00   1.0000   51.0000
omega____ theta____ kappa____ phi______ frames
    -      109.4303  -25.0000  -60.0000 49

#__ type_ start__ end____ width___ exp.time_
 10 omega   42.00   84.00   1.0000   51.0000
omega____ theta____ kappa____ phi______ frames
    -      109.4303  -38.0000 -180.0000 42

#__ type_ start__ end____ width___ exp.time_
 11 omega   92.00  177.00   1.0000   51.0000
omega____ theta____ kappa____ phi______ frames
    -      109.4303   50.0000   60.0000 85

#__ type_ start__ end____ width___ exp.time_
 12 omega   41.00   93.00   1.0000   51.0000
omega____ theta____ kappa____ phi______ frames
    -      109.4303  -25.0000 -116.0000 52

#__ type_ start__ end____ width___ exp.time_
 13 omega   41.00   66.00   1.0000   51.0000
omega____ theta____ kappa____ phi______ frames
    -      109.4303  -25.0000  -30.0000 25

#__ type_ start__ end____ width___ exp.time_
 14 omega   75.00  115.00   1.0000   51.0000
omega____ theta____ kappa____ phi______ frames
    -      109.4303 -111.0000   30.0000 40

#__ type_ start__ end____ width___ exp.time_
 15 omega   40.00  103.00   1.0000   51.0000
omega____ theta____ kappa____ phi______ frames
    -      109.4303  -50.0000   60.0000 63

#__ type_ start__ end____ width___ exp.time_
 16 omega  120.00  178.00   1.0000   51.0000
omega____ theta____ kappa____ phi______ frames
    -      109.4303  111.0000  -30.0000 58

#__ type_ start__ end____ width___ exp.time_
 17 omega   42.00  104.00   1.0000   51.0000
omega____ theta____ kappa____ phi______ frames
    -      109.4303  -50.0000 -120.0000 62
;
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0543250000
_diffrn_orient_matrix_UB_12      0.0827194000
_diffrn_orient_matrix_UB_13      0.0514587000
_diffrn_orient_matrix_UB_21      -0.0314432000
_diffrn_orient_matrix_UB_22      -0.0572904000
_diffrn_orient_matrix_UB_23      0.0839647000
_diffrn_orient_matrix_UB_31      0.0214381000
_diffrn_orient_matrix_UB_32      -0.2944317000
_diffrn_orient_matrix_UB_33      -0.0018343000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Enhance (Cu) X-ray Source'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                1663
_reflns_number_total             3383
_reflns_odcompleteness_completeness 99.06
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_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         0.624
_refine_diff_density_min         -0.511
_refine_diff_density_rms         0.073
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.135
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     195
_refine_ls_number_reflns         3383
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1948
_refine_ls_R_factor_gt           0.1155
_refine_ls_restrained_S_all      1.135
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0190P)²+8.7730P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2385
_refine_ls_wR_factor_ref         0.2629
_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:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C10(H10A,H10B), C13(H13A,H13B), C9(H9A,H9B), C15(H15A,H15B), C12(H12A,H12B),
 C14(H14A,H14B), C11(H11A,H11B), C17(H17A,H17B), C16(H16A,H16B), C18(H18A,H18B),
  C8(H8A,H8B), C19(H19A,H19B)
2.b Aromatic/amide H refined with riding coordinates:
 C5(H5), C4(H4)
2.c Idealised Me refined as rotating group:
 C20(H20A,H20B,H20C)
;
_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_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_refinement_flags_posn
S1 S 0.48491(9) -0.0786(4) 0.33637(13) 0.0461(5) Uani 1 d . . .
O21 O 0.3740(2) 0.0300(13) 0.3817(4) 0.070(2) Uani 1 d . . .
N6 N 0.4398(3) 0.2953(12) 0.4450(4) 0.0385(15) Uani 1 d . . .
N3 N 0.5396(2) 0.2803(13) 0.4269(4) 0.0435(16) Uani 1 d . . .
C2 C 0.4883(3) 0.1830(16) 0.4078(5) 0.0416(19) Uani 1 d . . .
C5 C 0.5589(3) -0.0612(19) 0.3306(5) 0.051(2) Uani 1 d . . .
H5 H 0.5814 -0.1726 0.2969 0.061 Uiso 1 calc . . R
C10 C 0.2377(3) 0.3892(17) 0.5294(5) 0.049(2) Uani 1 d . . .
H10A H 0.2332 0.5663 0.5036 0.059 Uiso 1 calc . . R
H10B H 0.2513 0.4150 0.5878 0.059 Uiso 1 calc . . R
C13 C 0.0755(3) 0.2627(16) 0.5784(5) 0.047(2) Uani 1 d . . .
H13A H 0.0628 0.2343 0.5197 0.057 Uiso 1 calc . . R
H13B H 0.0804 0.0867 0.6047 0.057 Uiso 1 calc . . R
C9 C 0.2824(3) 0.2325(16) 0.4808(5) 0.049(2) Uani 1 d . . .
H9A H 0.2688 0.2069 0.4224 0.059 Uiso 1 calc . . R
H9B H 0.2869 0.0554 0.5066 0.059 Uiso 1 calc . . R
C7 C 0.3846(3) 0.2139(17) 0.4294(5) 0.045(2) Uani 1 d . . .
C15 C -0.0287(3) 0.2699(17) 0.6249(5) 0.049(2) Uani 1 d . . .
H15A H -0.0413 0.2428 0.5661 0.059 Uiso 1 calc . . R
H15B H -0.0236 0.0932 0.6507 0.059 Uiso 1 calc . . R
C12 C 0.1334(3) 0.4073(18) 0.5784(5) 0.049(2) Uani 1 d . . .
H12A H 0.1285 0.5835 0.5521 0.059 Uiso 1 calc . . R
H12B H 0.1463 0.4352 0.6370 0.059 Uiso 1 calc . . R
C4 C 0.5789(3) 0.1313(17) 0.3805(5) 0.050(2) Uani 1 d . . .
H4 H 0.6182 0.1668 0.3847 0.060 Uiso 1 calc . . R
C14 C 0.0290(3) 0.4167(19) 0.6255(5) 0.052(2) Uani 1 d . . .
H14A H 0.0240 0.5928 0.5993 0.062 Uiso 1 calc . . R
H14B H 0.0416 0.4446 0.6843 0.062 Uiso 1 calc . . R
C11 C 0.1793(3) 0.2515(16) 0.5308(5) 0.048(2) Uani 1 d . . .
H11A H 0.1838 0.0752 0.5572 0.057 Uiso 1 calc . . R
H11B H 0.1660 0.2232 0.4724 0.057 Uiso 1 calc . . R
C17 C -0.1330(3) 0.2732(18) 0.6710(5) 0.052(2) Uani 1 d . . .
H17A H -0.1453 0.2471 0.6119 0.062 Uiso 1 calc . . R
H17B H -0.1276 0.0960 0.6963 0.062 Uiso 1 calc . . R
C16 C -0.0756(3) 0.4210(18) 0.6724(5) 0.0489(19) Uani 1 d . . .
H16A H -0.0631 0.4473 0.7313 0.059 Uiso 1 calc . . R
H16B H -0.0807 0.5979 0.6467 0.059 Uiso 1 calc . . R
C18 C -0.1805(3) 0.4183(19) 0.7180(5) 0.055(2) Uani 1 d . . .
H18A H -0.1689 0.4396 0.7775 0.065 Uiso 1 calc . . R
H18B H -0.1854 0.5974 0.6938 0.065 Uiso 1 calc . . R
C8 C 0.3407(3) 0.3719(18) 0.4797(5) 0.054(2) Uani 1 d . . .
H8A H 0.3362 0.5501 0.4547 0.064 Uiso 1 calc . . R
H8B H 0.3547 0.3944 0.5380 0.064 Uiso 1 calc . . R
C19 C -0.2376(3) 0.272(2) 0.7137(6) 0.064(3) Uani 1 d . . .
H19A H -0.2328 0.0940 0.7388 0.077 Uiso 1 calc . . R
H19B H -0.2487 0.2475 0.6541 0.077 Uiso 1 calc . . R
C20 C -0.2862(3) 0.418(2) 0.7593(6) 0.084(3) Uani 1 d . . .
H20A H -0.2917 0.5931 0.7344 0.126 Uiso 1 calc . . GR
H20B H -0.2763 0.4368 0.8188 0.126 Uiso 1 calc . . GR
H20C H -0.3210 0.3147 0.7534 0.126 Uiso 1 calc . . GR
H6 H 0.446(2) 0.444(11) 0.468(3) 0.001(13) Uiso 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 C2 1.711(8) . ?
S1 C5 1.726(7) . ?
O21 C7 1.200(9) . ?
N6 C2 1.393(9) . ?
N6 C7 1.363(9) . ?
N3 C2 1.315(9) . ?
N3 C4 1.389(9) . ?
C5 C4 1.312(11) . ?
C10 C9 1.512(9) . ?
C10 C11 1.519(9) . ?
C13 C12 1.523(9) . ?
C13 C14 1.523(9) . ?
C9 C8 1.520(9) . ?
C7 C8 1.517(10) . ?
C15 C14 1.525(10) . ?
C15 C16 1.524(9) . ?
C12 C11 1.521(9) . ?
C17 C16 1.522(10) . ?
C17 C18 1.518(10) . ?
C18 C19 1.512(10) . ?
C19 C20 1.526(11) . ?

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 S1 C5 87.8(4) . . ?
C7 N6 C2 124.9(7) . . ?
C2 N3 C4 106.8(6) . . ?
N6 C2 S1 123.1(6) . . ?
N3 C2 S1 117.2(5) . . ?
N3 C2 N6 119.7(7) . . ?
C4 C5 S1 110.4(6) . . ?
C9 C10 C11 113.5(7) . . ?
C14 C13 C12 113.5(7) . . ?
C10 C9 C8 113.1(7) . . ?
O21 C7 N6 121.2(7) . . ?
O21 C7 C8 125.5(7) . . ?
N6 C7 C8 113.2(7) . . ?
C16 C15 C14 113.5(7) . . ?
C11 C12 C13 112.8(7) . . ?
C5 C4 N3 117.8(7) . . ?
C13 C14 C15 112.9(7) . . ?
C10 C11 C12 114.4(7) . . ?
C18 C17 C16 114.2(7) . . ?
C17 C16 C15 113.0(7) . . ?
C19 C18 C17 113.4(7) . . ?
C7 C8 C9 112.3(7) . . ?
C18 C19 C20 114.1(8) . . ?

_database_code_depnum_ccdc_archive 'CCDC 966725'
_olex2_submission_special_instructions 'No special instructions were received'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_2d
_audit_creation_date             2014-09-26
_audit_creation_method           
;
Olex2 1.2
(compiled 2014.09.19 svn.r3010 for OlexSys, GUI svn.r4874)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C18 H32 N2 O S'
_chemical_formula_sum            'C18 H32 N2 O S'
_chemical_formula_weight         324.52
_chemical_melting_point          ?
_chemical_oxdiff_formula         C18H30N1O1S1
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'

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

_cell_length_a                   22.1166(2)
_cell_length_b                   19.4545(2)
_cell_length_c                   9.42062(13)
_cell_angle_alpha                90.00
_cell_angle_beta                 101.1861(13)
_cell_angle_gamma                90.00
_cell_volume                     3976.39(8)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    12334
_cell_measurement_temperature    298
_cell_measurement_theta_max      71.5104
_cell_measurement_theta_min      4.0717
_exptl_absorpt_coefficient_mu    1.460
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.53832
_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_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.084
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1424
_exptl_crystal_size_max          1.0
_exptl_crystal_size_mid          0.8
_exptl_crystal_size_min          0.56
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0352
_diffrn_reflns_av_unetI/netI     0.0199
_diffrn_reflns_limit_h_max       27
_diffrn_reflns_limit_h_min       -27
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            40767
_diffrn_reflns_theta_full        71.65
_diffrn_reflns_theta_max         71.65
_diffrn_reflns_theta_min         4.08
_diffrn_ambient_temperature      298.0
_diffrn_detector_area_resol_mean 16.1702
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -17.00   20.00   1.0000    2.9400
omega____ theta____ kappa____ phi______ frames
    -        0.0000   57.0000  -30.0000 37

#__ type_ start__ end____ width___ exp.time_
  2 omega  -77.00  -42.00   1.0000    2.9400
omega____ theta____ kappa____ phi______ frames
    -        0.0000  178.0000   90.0000 35

#__ type_ start__ end____ width___ exp.time_
  3 omega   26.00   69.00   1.0000    2.9400
omega____ theta____ kappa____ phi______ frames
    -        0.0000   57.0000  -30.0000 43

#__ type_ start__ end____ width___ exp.time_
  4 omega  -80.00  -28.00   1.0000   11.7700
omega____ theta____ kappa____ phi______ frames
    -      -42.5000  125.0000  -90.0000 52

#__ type_ start__ end____ width___ exp.time_
  5 omega  -90.00  -63.00   1.0000   11.7700
omega____ theta____ kappa____ phi______ frames
    -      -42.5000  -57.0000  120.0000 27

#__ type_ start__ end____ width___ exp.time_
  6 omega   32.00  126.00   1.0000   11.7700
omega____ theta____ kappa____ phi______ frames
    -       54.7558   77.0000  150.0000 94

#__ type_ start__ end____ width___ exp.time_
  7 omega   -8.00   63.00   1.0000   11.7700
omega____ theta____ kappa____ phi______ frames
    -       54.7558    0.0000 -180.0000 71

#__ type_ start__ end____ width___ exp.time_
  8 omega   -5.00   86.00   1.0000   11.7700
omega____ theta____ kappa____ phi______ frames
    -       54.7558  -77.0000   30.0000 91

#__ type_ start__ end____ width___ exp.time_
  9 omega   36.00   74.00   1.0000   11.7700
omega____ theta____ kappa____ phi______ frames
    -      109.5117  -25.0000 -120.0000 38

#__ type_ start__ end____ width___ exp.time_
 10 omega  142.00  175.00   1.0000   11.7700
omega____ theta____ kappa____ phi______ frames
    -      109.5117  145.0000 -178.0000 33

#__ type_ start__ end____ width___ exp.time_
 11 omega   89.00  139.00   1.0000   11.7700
omega____ theta____ kappa____ phi______ frames
    -      109.5117   50.0000  -90.0000 50

#__ type_ start__ end____ width___ exp.time_
 12 omega   36.00   67.00   1.0000   11.7700
omega____ theta____ kappa____ phi______ frames
    -      109.5117  -25.0000   90.0000 31

#__ type_ start__ end____ width___ exp.time_
 13 omega  100.00  150.00   1.0000   11.7700
omega____ theta____ kappa____ phi______ frames
    -      109.5117  111.0000  120.0000 50

#__ type_ start__ end____ width___ exp.time_
 14 omega   44.00   93.00   1.0000   11.7700
omega____ theta____ kappa____ phi______ frames
    -      109.5117  -38.0000  120.0000 49

#__ type_ start__ end____ width___ exp.time_
 15 omega   42.00   68.00   1.0000   11.7700
omega____ theta____ kappa____ phi______ frames
    -      109.5117  -38.0000 -150.0000 26

#__ type_ start__ end____ width___ exp.time_
 16 omega   38.00   92.00   1.0000   11.7700
omega____ theta____ kappa____ phi______ frames
    -      109.5117 -111.0000    0.0000 54

#__ type_ start__ end____ width___ exp.time_
 17 omega   37.00   70.00   1.0000   11.7700
omega____ theta____ kappa____ phi______ frames
    -      109.5117  -38.0000 -180.0000 33

#__ type_ start__ end____ width___ exp.time_
 18 omega   44.00  108.00   1.0000   11.7700
omega____ theta____ kappa____ phi______ frames
    -      109.5117 -111.0000 -180.0000 64

#__ type_ start__ end____ width___ exp.time_
 19 omega  153.00  178.00   1.0000   11.7700
omega____ theta____ kappa____ phi______ frames
    -      109.5117   50.0000  -90.0000 25

#__ type_ start__ end____ width___ exp.time_
 20 omega   44.00  138.00   1.0000   11.7700
omega____ theta____ kappa____ phi______ frames
    -      109.5117  -77.0000 -180.0000 94

#__ type_ start__ end____ width___ exp.time_
 21 omega  -27.00   73.00   1.0000    2.9400
omega____ theta____ kappa____ phi______ frames
    -        0.0000   38.0000  150.0000 100

#__ type_ start__ end____ width___ exp.time_
 22 omega  -69.00   22.00   1.0000    2.9400
omega____ theta____ kappa____ phi______ frames
    -        0.0000  -57.0000 -180.0000 91

#__ type_ start__ end____ width___ exp.time_
 23 omega -112.00  -61.00   1.0000   11.7700
omega____ theta____ kappa____ phi______ frames
    -      -42.5000 -145.0000  178.0000 51

#__ type_ start__ end____ width___ exp.time_
 24 omega -113.00  -11.00   1.0000   11.7700
omega____ theta____ kappa____ phi______ frames
    -      -42.5000  -77.0000  -30.0000 102

#__ type_ start__ end____ width___ exp.time_
 25 omega -113.00  -11.00   1.0000   11.7700
omega____ theta____ kappa____ phi______ frames
    -      -42.5000  -77.0000   60.0000 102

#__ type_ start__ end____ width___ exp.time_
 26 omega  -14.00   76.00   1.0000   11.7700
omega____ theta____ kappa____ phi______ frames
    -       54.7558  -57.0000  150.0000 90

#__ type_ start__ end____ width___ exp.time_
 27 omega   23.00  126.00   1.0000   11.7700
omega____ theta____ kappa____ phi______ frames
    -       54.7558   77.0000 -120.0000 103

#__ type_ start__ end____ width___ exp.time_
 28 omega   27.00  127.00   1.0000   11.7700
omega____ theta____ kappa____ phi______ frames
    -       54.7558   38.0000    0.0000 100

#__ type_ start__ end____ width___ exp.time_
 29 omega   78.00  178.00   1.0000   11.7700
omega____ theta____ kappa____ phi______ frames
    -      109.5117   77.0000 -150.0000 100

#__ type_ start__ end____ width___ exp.time_
 30 omega   82.00  178.00   1.0000   11.7700
omega____ theta____ kappa____ phi______ frames
    -      109.5117   38.0000  -30.0000 96

#__ type_ start__ end____ width___ exp.time_
 31 omega   82.00  178.00   1.0000   11.7700
omega____ theta____ kappa____ phi______ frames
    -      109.5117   38.0000  150.0000 96

#__ type_ start__ end____ width___ exp.time_
 32 omega   37.00   93.00   1.0000   11.7700
omega____ theta____ kappa____ phi______ frames
    -      109.5117  -38.0000   30.0000 56

#__ type_ start__ end____ width___ exp.time_
 33 omega   37.00  178.00   1.0000   11.7700
omega____ theta____ kappa____ phi______ frames
    -      109.5117   12.0000   90.0000 141

#__ type_ start__ end____ width___ exp.time_
 34 omega   37.00  149.00   1.0000   11.7700
omega____ theta____ kappa____ phi______ frames
    -      109.5117  -92.0000 -120.0000 112

#__ type_ start__ end____ width___ exp.time_
 35 omega   78.00  178.00   1.0000   11.7700
omega____ theta____ kappa____ phi______ frames
    -      109.5117   77.0000 -180.0000 100

#__ type_ start__ end____ width___ exp.time_
 36 omega   36.00  114.00   1.0000   11.7700
omega____ theta____ kappa____ phi______ frames
    -      109.5117 -111.0000  120.0000 78
;
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0647927000
_diffrn_orient_matrix_UB_12      0.0302572000
_diffrn_orient_matrix_UB_13      -0.0530662000
_diffrn_orient_matrix_UB_21      0.0286302000
_diffrn_orient_matrix_UB_22      0.0712904000
_diffrn_orient_matrix_UB_23      -0.0141369000
_diffrn_orient_matrix_UB_31      0.0047311000
_diffrn_orient_matrix_UB_32      -0.0165754000
_diffrn_orient_matrix_UB_33      -0.1573746000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Enhance (Cu) X-ray Source'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                6244
_reflns_number_total             7711
_reflns_odcompleteness_completeness 99.95
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_threshold_expression     >2sigma(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  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'olex2.solve (Bourhis et al., 2013)'
_refine_diff_density_max         0.313
_refine_diff_density_min         -0.189
_refine_diff_density_rms         0.036
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     409
_refine_ls_number_reflns         7711
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0605
_refine_ls_R_factor_gt           0.0493
_refine_ls_restrained_S_all      1.032
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0725P)²+1.0320P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1351
_refine_ls_wR_factor_ref         0.1468
_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:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B), C11(H11A,H11B), C13(H13A,H13B), C14(H14A,H14B), C15(H15A,H15B),
 C19(H19A,H19B), C20(H20A,H20B), C21(H21A,H21B), C24(H24A,H24B), C25(H25A,H25B),
  C27(H27A,H27B), C28(H28A,H28B), C29(H29A,H29B), C30(H30A,H30B), C31(H31A,
 H31B), C32(H32A,H32B), C33(H33A,H33B), C35(H35A,H35B), C37(H37A,H37B),
 C39(H39A,H39B), C40(H40A,H40B), C41(H41A,H41B), C42(H42A,H42B), C43(H43A,H43B)
2.b Aromatic/amide H refined with riding coordinates:
 C23(H23), C34(H34)
2.c Idealised Me refined as rotating group:
 C22(H22A,H22B,H22C), C36(H36A,H36B,H36C), C38(H38A,H38B,H38C), C44(H44A,H44B,
 H44C)
;
_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_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_refinement_flags_posn
S1 S 0.96519(2) 0.68402(2) 0.45836(6) 0.06029(16) Uani 1 d . . .
S2 S 0.16235(3) 0.56217(2) 0.06606(6) 0.06978(17) Uani 1 d . . .
N3 N 1.02145(7) 0.79475(7) 0.60519(16) 0.0492(3) Uani 1 d . . .
N4 N 0.93760(6) 0.81118(7) 0.41389(16) 0.0486(3) Uani 1 d . . .
O5 O 0.05545(6) 0.56121(5) 0.17318(15) 0.0609(3) Uani 1 d . . .
O6 O 1.05914(7) 0.69203(6) 0.68470(18) 0.0767(5) Uani 1 d . . .
N7 N 0.08479(7) 0.45731(7) 0.10694(17) 0.0521(4) Uani 1 d . . .
N8 N 0.17133(7) 0.43404(8) 0.00779(19) 0.0633(4) Uani 1 d . . .
C9 C 1.15510(8) 0.74315(9) 0.8965(2) 0.0538(4) Uani 1 d . . .
H9A H 1.1743 0.7141 0.8340 0.065 Uiso 1 calc . . R
H9B H 1.1332 0.7136 0.9522 0.065 Uiso 1 calc . . R
C10 C 0.97547(7) 0.77055(8) 0.49644(18) 0.0443(4) Uani 1 d . . .
C11 C 1.10962(8) 0.79083(9) 0.8041(2) 0.0531(4) Uani 1 d . . .
H11A H 1.0890 0.8180 0.8668 0.064 Uiso 1 calc . . R
H11B H 1.1321 0.8222 0.7533 0.064 Uiso 1 calc . . R
C12 C 0.04718(8) 0.49882(8) 0.16594(18) 0.0481(4) Uani 1 d . . .
C13 C 1.30423(9) 0.77723(11) 1.1854(2) 0.0673(5) Uani 1 d . . .
H13A H 1.3235 0.8073 1.1252 0.081 Uiso 1 calc . . R
H13B H 1.2857 0.8060 1.2495 0.081 Uiso 1 calc . . R
C14 C -0.00381(8) 0.46273(8) 0.2210(2) 0.0519(4) Uani 1 d . . .
H14A H 0.0141 0.4272 0.2885 0.062 Uiso 1 calc . . R
H14B H -0.0304 0.4404 0.1403 0.062 Uiso 1 calc . . R
C15 C 1.20489(8) 0.78209(10) 0.9991(2) 0.0579(4) Uani 1 d . . .
H15A H 1.2250 0.8135 0.9430 0.070 Uiso 1 calc . . R
H15B H 1.1855 0.8094 1.0639 0.070 Uiso 1 calc . . R
C16 C 1.06201(8) 0.75405(8) 0.69566(19) 0.0498(4) Uani 1 d . . .
C17 C 0.89677(8) 0.77362(9) 0.3119(2) 0.0531(4) Uani 1 d . . .
C18 C 0.13720(8) 0.47791(9) 0.05954(19) 0.0520(4) Uani 1 d . . .
C19 C 1.25350(9) 0.73666(10) 1.0887(2) 0.0614(5) Uani 1 d . . .
H19A H 1.2718 0.7079 1.0243 0.074 Uiso 1 calc . . R
H19B H 1.2339 0.7067 1.1486 0.074 Uiso 1 calc . . R
C20 C -0.09280(9) 0.47093(9) 0.3515(2) 0.0577(4) Uani 1 d . . .
H20A H -0.0736 0.4372 0.4217 0.069 Uiso 1 calc . . R
H20B H -0.1177 0.4463 0.2715 0.069 Uiso 1 calc . . R
C21 C -0.04270(8) 0.50960(9) 0.2957(2) 0.0536(4) Uani 1 d . . .
H21A H -0.0163 0.5325 0.3760 0.064 Uiso 1 calc . . R
H21B H -0.0615 0.5447 0.2281 0.064 Uiso 1 calc . . R
C22 C 0.84861(10) 0.81130(11) 0.2073(3) 0.0744(6) Uani 1 d . . .
H22A H 0.8199 0.8322 0.2585 0.112 Uiso 1 calc . . GR
H22B H 0.8272 0.7796 0.1369 0.112 Uiso 1 calc . . GR
H22C H 0.8678 0.8462 0.1593 0.112 Uiso 1 calc . . GR
C23 C 0.90527(9) 0.70578(10) 0.3201(2) 0.0621(5) Uani 1 d . . .
H23 H 0.8818 0.6742 0.2589 0.074 Uiso 1 calc . . R
C24 C 1.35363(9) 0.73319(12) 1.2760(2) 0.0714(6) Uani 1 d . . .
H24A H 1.3715 0.7036 1.2123 0.086 Uiso 1 calc . . R
H24B H 1.3346 0.7040 1.3385 0.086 Uiso 1 calc . . R
C25 C 1.45503(10) 0.73177(14) 1.4582(3) 0.0800(7) Uani 1 d . . .
H25A H 1.4725 0.7019 1.3943 0.096 Uiso 1 calc . . R
H25B H 1.4370 0.7028 1.5229 0.096 Uiso 1 calc . . R
C26 C 0.22170(9) 0.46685(12) -0.0294(2) 0.0709(5) Uani 1 d . . .
C27 C 1.55738(11) 0.73116(14) 1.6355(3) 0.0855(7) Uani 1 d . . .
H27A H 1.5739 0.7008 1.5707 0.103 Uiso 1 calc . . R
H27B H 1.5398 0.7026 1.7016 0.103 Uiso 1 calc . . R
C28 C 1.40465(10) 0.77450(13) 1.3685(3) 0.0777(6) Uani 1 d . . .
H28A H 1.4230 0.8043 1.3058 0.093 Uiso 1 calc . . R
H28B H 1.3867 0.8036 1.4329 0.093 Uiso 1 calc . . R
C29 C -0.13470(9) 0.51609(9) 0.4213(2) 0.0613(5) Uani 1 d . . .
H29A H -0.1103 0.5389 0.5047 0.074 Uiso 1 calc . . R
H29B H -0.1525 0.5513 0.3530 0.074 Uiso 1 calc . . R
C30 C -0.23082(10) 0.51917(11) 0.5337(3) 0.0726(6) Uani 1 d . . .
H30A H -0.2476 0.5548 0.4654 0.087 Uiso 1 calc . . R
H30B H -0.2085 0.5415 0.6203 0.087 Uiso 1 calc . . R
C31 C -0.18613(10) 0.47628(10) 0.4688(2) 0.0666(5) Uani 1 d . . .
H31A H -0.2090 0.4519 0.3857 0.080 Uiso 1 calc . . R
H31B H -0.1679 0.4422 0.5394 0.080 Uiso 1 calc . . R
C32 C 1.50646(11) 0.77392(14) 1.5473(3) 0.0831(7) Uani 1 d . . .
H32A H 1.5241 0.8034 1.4828 0.100 Uiso 1 calc . . R
H32B H 1.4891 0.8033 1.6123 0.100 Uiso 1 calc . . R
C33 C 1.60990(11) 0.77247(14) 1.7221(3) 0.0890(7) Uani 1 d . . .
H33A H 1.6274 0.8014 1.6565 0.107 Uiso 1 calc . . R
H33B H 1.5936 0.8024 1.7881 0.107 Uiso 1 calc . . R
C34 C 0.22373(10) 0.53468(13) -0.0056(3) 0.0812(6) Uani 1 d . . .
H34 H 0.2547 0.5634 -0.0255 0.097 Uiso 1 calc . . R
C35 C -0.28368(11) 0.47825(12) 0.5726(3) 0.0778(6) Uani 1 d . . .
H35A H -0.3049 0.4543 0.4869 0.093 Uiso 1 calc . . R
H35B H -0.2670 0.4439 0.6441 0.093 Uiso 1 calc . . R
C36 C 0.26673(12) 0.42397(16) -0.0904(3) 0.1029(9) Uani 1 d . . .
H36A H 0.2877 0.3935 -0.0170 0.154 Uiso 1 calc . . GR
H36B H 0.2962 0.4533 -0.1228 0.154 Uiso 1 calc . . GR
H36C H 0.2451 0.3976 -0.1705 0.154 Uiso 1 calc . . GR
C37 C 1.66052(13) 0.72873(17) 1.8081(3) 0.1054(10) Uani 1 d . . .
H37A H 1.6431 0.7004 1.8749 0.126 Uiso 1 calc . . R
H37B H 1.6762 0.6982 1.7423 0.126 Uiso 1 calc . . R
C38 C 1.71332(14) 0.76929(19) 1.8924(4) 0.1307(13) Uani 1 d . . .
H38A H 1.7330 0.7947 1.8267 0.196 Uiso 1 calc . . GR
H38B H 1.7425 0.7385 1.9483 0.196 Uiso 1 calc . . GR
H38C H 1.6982 0.8006 1.9560 0.196 Uiso 1 calc . . GR
C39 C -0.38273(14) 0.48069(15) 0.6713(4) 0.1043(9) Uani 1 d . . .
H39A H -0.4013 0.4527 0.5891 0.125 Uiso 1 calc . . R
H39B H -0.3665 0.4500 0.7506 0.125 Uiso 1 calc . . R
C40 C -0.32977(12) 0.52168(14) 0.6316(3) 0.0901(7) Uani 1 d . . .
H40A H -0.3465 0.5560 0.5600 0.108 Uiso 1 calc . . R
H40B H -0.3085 0.5458 0.7170 0.108 Uiso 1 calc . . R
C41 C -0.43160(14) 0.52514(17) 0.7144(4) 0.1124(10) Uani 1 d . . .
H41A H -0.4458 0.5577 0.6370 0.135 Uiso 1 calc . . R
H41B H -0.4132 0.5513 0.7995 0.135 Uiso 1 calc . . R
C42 C -0.53526(16) 0.5343(2) 0.7833(5) 0.1428(14) Uani 1 d . . .
H42A H -0.5172 0.5614 0.8675 0.171 Uiso 1 calc . . R
H42B H -0.5479 0.5659 0.7033 0.171 Uiso 1 calc . . R
C43 C -0.48675(15) 0.48664(18) 0.7467(4) 0.1192(11) Uani 1 d . . .
H43A H -0.5046 0.4591 0.6633 0.143 Uiso 1 calc . . R
H43B H -0.4733 0.4557 0.8273 0.143 Uiso 1 calc . . R
C44 C -0.59031(18) 0.4986(3) 0.8133(6) 0.1747(19) Uani 1 d . . .
H44A H -0.6083 0.4713 0.7310 0.262 Uiso 1 calc . . GR
H44B H -0.6198 0.5318 0.8323 0.262 Uiso 1 calc . . GR
H44C H -0.5786 0.4693 0.8962 0.262 Uiso 1 calc . . GR
H3 H 1.0248(8) 0.8325(9) 0.6146(19) 0.041(5) Uiso 1 d . . .
H7 H 0.0766(9) 0.4149(10) 0.098(2) 0.055(5) Uiso 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 C10 1.7271(15) . ?
S1 C23 1.721(2) . ?
S2 C18 1.7283(17) . ?
S2 C34 1.715(3) . ?
N3 C10 1.379(2) . ?
N3 C16 1.364(2) . ?
N3 H3 0.743(17) . ?
N4 C10 1.296(2) . ?
N4 C17 1.392(2) . ?
O5 C12 1.2274(19) . ?
O6 C16 1.212(2) . ?
N7 C12 1.354(2) . ?
N7 C18 1.380(2) . ?
N7 H7 0.84(2) . ?
N8 C18 1.296(2) . ?
N8 C26 1.387(3) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C9 C11 1.513(2) . ?
C9 C15 1.519(2) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C11 C16 1.499(2) . ?
C12 C14 1.504(2) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C13 C19 1.521(3) . ?
C13 C24 1.515(3) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C14 C21 1.517(2) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C15 C19 1.516(2) . ?
C17 C22 1.495(3) . ?
C17 C23 1.333(3) . ?
C19 H19A 0.9700 . ?
C19 H19B 0.9700 . ?
C20 H20A 0.9700 . ?
C20 H20B 0.9700 . ?
C20 C21 1.515(3) . ?
C20 C29 1.516(3) . ?
C21 H21A 0.9700 . ?
C21 H21B 0.9700 . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?
C23 H23 0.9300 . ?
C24 H24A 0.9700 . ?
C24 H24B 0.9700 . ?
C24 C28 1.515(3) . ?
C25 H25A 0.9700 . ?
C25 H25B 0.9700 . ?
C25 C28 1.510(3) . ?
C25 C32 1.517(3) . ?
C26 C34 1.338(3) . ?
C26 C36 1.497(3) . ?
C27 H27A 0.9700 . ?
C27 H27B 0.9700 . ?
C27 C32 1.512(3) . ?
C27 C33 1.514(3) . ?
C28 H28A 0.9700 . ?
C28 H28B 0.9700 . ?
C29 H29A 0.9700 . ?
C29 H29B 0.9700 . ?
C29 C31 1.514(3) . ?
C30 H30A 0.9700 . ?
C30 H30B 0.9700 . ?
C30 C31 1.511(3) . ?
C30 C35 1.517(3) . ?
C31 H31A 0.9700 . ?
C31 H31B 0.9700 . ?
C32 H32A 0.9700 . ?
C32 H32B 0.9700 . ?
C33 H33A 0.9700 . ?
C33 H33B 0.9700 . ?
C33 C37 1.511(3) . ?
C34 H34 0.9300 . ?
C35 H35A 0.9700 . ?
C35 H35B 0.9700 . ?
C35 C40 1.511(3) . ?
C36 H36A 0.9600 . ?
C36 H36B 0.9600 . ?
C36 H36C 0.9600 . ?
C37 H37A 0.9700 . ?
C37 H37B 0.9700 . ?
C37 C38 1.502(4) . ?
C38 H38A 0.9600 . ?
C38 H38B 0.9600 . ?
C38 H38C 0.9600 . ?
C39 H39A 0.9700 . ?
C39 H39B 0.9700 . ?
C39 C40 1.522(3) . ?
C39 C41 1.500(4) . ?
C40 H40A 0.9700 . ?
C40 H40B 0.9700 . ?
C41 H41A 0.9700 . ?
C41 H41B 0.9700 . ?
C41 C43 1.512(4) . ?
C42 H42A 0.9700 . ?
C42 H42B 0.9700 . ?
C42 C43 1.508(5) . ?
C42 C44 1.476(5) . ?
C43 H43A 0.9700 . ?
C43 H43B 0.9700 . ?
C44 H44A 0.9600 . ?
C44 H44B 0.9600 . ?
C44 H44C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C23 S1 C10 88.19(8) . . ?
C34 S2 C18 87.94(10) . . ?
C10 N3 H3 118.0(14) . . ?
C16 N3 C10 124.53(14) . . ?
C16 N3 H3 117.5(14) . . ?
C10 N4 C17 110.58(14) . . ?
C12 N7 C18 125.53(15) . . ?
C12 N7 H7 119.3(13) . . ?
C18 N7 H7 115.2(13) . . ?
C18 N8 C26 110.32(17) . . ?
H9A C9 H9B 107.9 . . ?
C11 C9 H9A 109.2 . . ?
C11 C9 H9B 109.2 . . ?
C11 C9 C15 112.27(15) . . ?
C15 C9 H9A 109.2 . . ?
C15 C9 H9B 109.2 . . ?
N3 C10 S1 122.38(12) . . ?
N4 C10 S1 115.23(12) . . ?
N4 C10 N3 122.38(14) . . ?
C9 C11 H11A 108.9 . . ?
C9 C11 H11B 108.9 . . ?
H11A C11 H11B 107.7 . . ?
C16 C11 C9 113.57(14) . . ?
C16 C11 H11A 108.9 . . ?
C16 C11 H11B 108.9 . . ?
O5 C12 N7 121.06(17) . . ?
O5 C12 C14 123.79(16) . . ?
N7 C12 C14 115.14(14) . . ?
H13A C13 H13B 107.6 . . ?
C19 C13 H13A 108.7 . . ?
C19 C13 H13B 108.7 . . ?
C24 C13 H13A 108.7 . . ?
C24 C13 H13B 108.7 . . ?
C24 C13 C19 114.30(18) . . ?
C12 C14 H14A 108.7 . . ?
C12 C14 H14B 108.7 . . ?
C12 C14 C21 114.22(14) . . ?
H14A C14 H14B 107.6 . . ?
C21 C14 H14A 108.7 . . ?
C21 C14 H14B 108.7 . . ?
C9 C15 H15A 108.7 . . ?
C9 C15 H15B 108.7 . . ?
H15A C15 H15B 107.6 . . ?
C19 C15 C9 114.33(16) . . ?
C19 C15 H15A 108.7 . . ?
C19 C15 H15B 108.7 . . ?
N3 C16 C11 116.01(14) . . ?
O6 C16 N3 120.49(16) . . ?
O6 C16 C11 123.49(15) . . ?
N4 C17 C22 118.78(15) . . ?
C23 C17 N4 114.47(16) . . ?
C23 C17 C22 126.74(17) . . ?
N7 C18 S2 123.28(14) . . ?
N8 C18 S2 115.54(14) . . ?
N8 C18 N7 121.18(16) . . ?
C13 C19 H19A 109.0 . . ?
C13 C19 H19B 109.0 . . ?
C15 C19 C13 113.08(17) . . ?
C15 C19 H19A 109.0 . . ?
C15 C19 H19B 109.0 . . ?
H19A C19 H19B 107.8 . . ?
H20A C20 H20B 107.6 . . ?
C21 C20 H20A 108.7 . . ?
C21 C20 H20B 108.7 . . ?
C21 C20 C29 114.36(15) . . ?
C29 C20 H20A 108.7 . . ?
C29 C20 H20B 108.7 . . ?
C14 C21 H21A 109.1 . . ?
C14 C21 H21B 109.1 . . ?
C20 C21 C14 112.41(14) . . ?
C20 C21 H21A 109.1 . . ?
C20 C21 H21B 109.1 . . ?
H21A C21 H21B 107.9 . . ?
C17 C22 H22A 109.5 . . ?
C17 C22 H22B 109.5 . . ?
C17 C22 H22C 109.5 . . ?
H22A C22 H22B 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
S1 C23 H23 124.2 . . ?
C17 C23 S1 111.53(14) . . ?
C17 C23 H23 124.2 . . ?
C13 C24 H24A 108.9 . . ?
C13 C24 H24B 108.9 . . ?
C13 C24 C28 113.53(19) . . ?
H24A C24 H24B 107.7 . . ?
C28 C24 H24A 108.9 . . ?
C28 C24 H24B 108.9 . . ?
H25A C25 H25B 107.7 . . ?
C28 C25 H25A 108.8 . . ?
C28 C25 H25B 108.8 . . ?
C28 C25 C32 113.9(2) . . ?
C32 C25 H25A 108.8 . . ?
C32 C25 H25B 108.8 . . ?
N8 C26 C36 117.9(2) . . ?
C34 C26 N8 114.5(2) . . ?
C34 C26 C36 127.7(2) . . ?
H27A C27 H27B 107.6 . . ?
C32 C27 H27A 108.6 . . ?
C32 C27 H27B 108.6 . . ?
C32 C27 C33 114.6(2) . . ?
C33 C27 H27A 108.6 . . ?
C33 C27 H27B 108.6 . . ?
C24 C28 H28A 108.6 . . ?
C24 C28 H28B 108.6 . . ?
C25 C28 C24 114.6(2) . . ?
C25 C28 H28A 108.6 . . ?
C25 C28 H28B 108.6 . . ?
H28A C28 H28B 107.6 . . ?
C20 C29 H29A 109.0 . . ?
C20 C29 H29B 109.0 . . ?
H29A C29 H29B 107.8 . . ?
C31 C29 C20 112.92(16) . . ?
C31 C29 H29A 109.0 . . ?
C31 C29 H29B 109.0 . . ?
H30A C30 H30B 107.7 . . ?
C31 C30 H30A 108.8 . . ?
C31 C30 H30B 108.8 . . ?
C31 C30 C35 113.78(19) . . ?
C35 C30 H30A 108.8 . . ?
C35 C30 H30B 108.8 . . ?
C29 C31 H31A 108.5 . . ?
C29 C31 H31B 108.5 . . ?
C30 C31 C29 115.18(17) . . ?
C30 C31 H31A 108.5 . . ?
C30 C31 H31B 108.5 . . ?
H31A C31 H31B 107.5 . . ?
C25 C32 H32A 108.8 . . ?
C25 C32 H32B 108.8 . . ?
C27 C32 C25 113.9(2) . . ?
C27 C32 H32A 108.8 . . ?
C27 C32 H32B 108.8 . . ?
H32A C32 H32B 107.7 . . ?
C27 C33 H33A 108.8 . . ?
C27 C33 H33B 108.8 . . ?
H33A C33 H33B 107.7 . . ?
C37 C33 C27 113.7(2) . . ?
C37 C33 H33A 108.8 . . ?
C37 C33 H33B 108.8 . . ?
S2 C34 H34 124.1 . . ?
C26 C34 S2 111.74(17) . . ?
C26 C34 H34 124.1 . . ?
C30 C35 H35A 108.8 . . ?
C30 C35 H35B 108.8 . . ?
H35A C35 H35B 107.7 . . ?
C40 C35 C30 113.7(2) . . ?
C40 C35 H35A 108.8 . . ?
C40 C35 H35B 108.8 . . ?
C26 C36 H36A 109.5 . . ?
C26 C36 H36B 109.5 . . ?
C26 C36 H36C 109.5 . . ?
H36A C36 H36B 109.5 . . ?
H36A C36 H36C 109.5 . . ?
H36B C36 H36C 109.5 . . ?
C33 C37 H37A 108.8 . . ?
C33 C37 H37B 108.8 . . ?
H37A C37 H37B 107.6 . . ?
C38 C37 C33 114.0(3) . . ?
C38 C37 H37A 108.8 . . ?
C38 C37 H37B 108.8 . . ?
C37 C38 H38A 109.5 . . ?
C37 C38 H38B 109.5 . . ?
C37 C38 H38C 109.5 . . ?
H38A C38 H38B 109.5 . . ?
H38A C38 H38C 109.5 . . ?
H38B C38 H38C 109.5 . . ?
H39A C39 H39B 107.8 . . ?
C40 C39 H39A 108.9 . . ?
C40 C39 H39B 108.9 . . ?
C41 C39 H39A 108.9 . . ?
C41 C39 H39B 108.9 . . ?
C41 C39 C40 113.2(2) . . ?
C35 C40 C39 113.8(2) . . ?
C35 C40 H40A 108.8 . . ?
C35 C40 H40B 108.8 . . ?
C39 C40 H40A 108.8 . . ?
C39 C40 H40B 108.8 . . ?
H40A C40 H40B 107.7 . . ?
C39 C41 H41A 108.5 . . ?
C39 C41 H41B 108.5 . . ?
C39 C41 C43 114.9(3) . . ?
H41A C41 H41B 107.5 . . ?
C43 C41 H41A 108.5 . . ?
C43 C41 H41B 108.5 . . ?
H42A C42 H42B 107.7 . . ?
C43 C42 H42A 108.8 . . ?
C43 C42 H42B 108.8 . . ?
C44 C42 H42A 108.8 . . ?
C44 C42 H42B 108.8 . . ?
C44 C42 C43 113.8(4) . . ?
C41 C43 H43A 109.2 . . ?
C41 C43 H43B 109.2 . . ?
C42 C43 C41 112.3(3) . . ?
C42 C43 H43A 109.2 . . ?
C42 C43 H43B 109.2 . . ?
H43A C43 H43B 107.9 . . ?
C42 C44 H44A 109.5 . . ?
C42 C44 H44B 109.5 . . ?
C42 C44 H44C 109.5 . . ?
H44A C44 H44B 109.5 . . ?
H44A C44 H44C 109.5 . . ?
H44B C44 H44C 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
N4 C17 C23 S1 0.4(2) . . . . ?
O5 C12 C14 C21 -3.5(2) . . . . ?
N7 C12 C14 C21 176.08(14) . . . . ?
N8 C26 C34 S2 0.2(3) . . . . ?
C9 C11 C16 N3 -177.23(16) . . . . ?
C9 C11 C16 O6 1.6(3) . . . . ?
C9 C15 C19 C13 177.42(17) . . . . ?
C10 S1 C23 C17 -0.34(16) . . . . ?
C10 N3 C16 O6 -0.5(3) . . . . ?
C10 N3 C16 C11 178.38(16) . . . . ?
C10 N4 C17 C22 179.16(17) . . . . ?
C10 N4 C17 C23 -0.3(2) . . . . ?
C11 C9 C15 C19 -177.07(16) . . . . ?
C12 N7 C18 S2 -1.1(3) . . . . ?
C12 N7 C18 N8 178.19(17) . . . . ?
C12 C14 C21 C20 -179.08(14) . . . . ?
C13 C24 C28 C25 -179.1(2) . . . . ?
C15 C9 C11 C16 176.65(16) . . . . ?
C16 N3 C10 S1 -1.9(2) . . . . ?
C16 N3 C10 N4 179.35(16) . . . . ?
C17 N4 C10 S1 0.01(19) . . . . ?
C17 N4 C10 N3 178.84(15) . . . . ?
C18 S2 C34 C26 0.14(19) . . . . ?
C18 N7 C12 O5 4.9(3) . . . . ?
C18 N7 C12 C14 -174.77(15) . . . . ?
C18 N8 C26 C34 -0.5(3) . . . . ?
C18 N8 C26 C36 179.6(2) . . . . ?
C19 C13 C24 C28 178.42(19) . . . . ?
C20 C29 C31 C30 -177.68(18) . . . . ?
C21 C20 C29 C31 177.05(16) . . . . ?
C22 C17 C23 S1 -178.96(18) . . . . ?
C23 S1 C10 N3 -178.65(16) . . . . ?
C23 S1 C10 N4 0.19(15) . . . . ?
C24 C13 C19 C15 -179.82(18) . . . . ?
C26 N8 C18 S2 0.6(2) . . . . ?
C26 N8 C18 N7 -178.76(16) . . . . ?
C27 C33 C37 C38 179.0(3) . . . . ?
C28 C25 C32 C27 -179.2(2) . . . . ?
C29 C20 C21 C14 -177.46(15) . . . . ?
C30 C35 C40 C39 -179.8(2) . . . . ?
C31 C30 C35 C40 -177.6(2) . . . . ?
C32 C25 C28 C24 178.6(2) . . . . ?
C32 C27 C33 C37 -179.4(2) . . . . ?
C33 C27 C32 C25 178.5(2) . . . . ?
C34 S2 C18 N7 178.91(17) . . . . ?
C34 S2 C18 N8 -0.45(16) . . . . ?
C35 C30 C31 C29 176.84(19) . . . . ?
C36 C26 C34 S2 -179.9(2) . . . . ?
C39 C41 C43 C42 -177.6(3) . . . . ?
C40 C39 C41 C43 176.8(3) . . . . ?
C41 C39 C40 C35 -173.7(3) . . . . ?
C44 C42 C43 C41 179.1(4) . . . . ?

_database_code_depnum_ccdc_archive 'CCDC 957407'
_olex2_submission_special_instructions 'No special instructions were received'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_3c
_audit_creation_date             2014-09-26
_audit_creation_method           
;
Olex2 1.2
(compiled 2014.09.19 svn.r3010 for OlexSys, GUI svn.r4874)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C17 H30 N2 O S'
_chemical_formula_sum            'C17 H30 N2 O S'
_chemical_formula_weight         310.49
_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 0.0181 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'

_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_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, -y, -z'

_cell_length_a                   4.9139(3)
_cell_length_b                   8.2041(5)
_cell_length_c                   23.1603(10)
_cell_angle_alpha                84.043(4)
_cell_angle_beta                 87.033(4)
_cell_angle_gamma                78.743(5)
_cell_volume                     910.31(8)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    2831
_cell_measurement_temperature    293
_cell_measurement_theta_max      71.9350
_cell_measurement_theta_min      3.7810
_exptl_absorpt_coefficient_mu    1.575
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.76277
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
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    1.133
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             340
_exptl_crystal_size_max          0.54
_exptl_crystal_size_mid          0.45
_exptl_crystal_size_min          0.15
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0253
_diffrn_reflns_av_unetI/netI     0.0402
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            5668
_diffrn_reflns_theta_full        72.18
_diffrn_reflns_theta_max         72.18
_diffrn_reflns_theta_min         3.84
_diffrn_ambient_temperature      293
_diffrn_detector_area_resol_mean 8.0851
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -43.00   30.00   1.0000    2.4100
omega____ theta____ kappa____ phi______ frames
    -      -42.5000   38.0000  -60.0000 73

#__ type_ start__ end____ width___ exp.time_
  2 omega  -42.00   30.00   1.0000    2.4100
omega____ theta____ kappa____ phi______ frames
    -      -42.5000   25.0000   30.0000 72

#__ type_ start__ end____ width___ exp.time_
  3 omega -105.00  -21.00   1.0000    2.4100
omega____ theta____ kappa____ phi______ frames
    -      -42.5000  -57.0000 -180.0000 84

#__ type_ start__ end____ width___ exp.time_
  4 omega  -96.00  -42.00   1.0000    2.4100
omega____ theta____ kappa____ phi______ frames
    -      -42.5000  125.0000 -180.0000 54

#__ type_ start__ end____ width___ exp.time_
  5 omega    0.00   83.00   1.0000    2.4100
omega____ theta____ kappa____ phi______ frames
    -       55.0276  -77.0000  -60.0000 83

#__ type_ start__ end____ width___ exp.time_
  6 omega   17.00   60.00   1.0000    2.4100
omega____ theta____ kappa____ phi______ frames
    -       55.0276  -38.0000   60.0000 43

#__ type_ start__ end____ width___ exp.time_
  7 omega   87.00  118.00   1.0000    2.4100
omega____ theta____ kappa____ phi______ frames
    -       55.0276   57.0000 -150.0000 31

#__ type_ start__ end____ width___ exp.time_
  8 omega   28.00  117.00   1.0000    2.4100
omega____ theta____ kappa____ phi______ frames
    -       55.0276   77.0000   60.0000 89

#__ type_ start__ end____ width___ exp.time_
  9 omega   43.00   82.00   1.0000    9.6600
omega____ theta____ kappa____ phi______ frames
    -      110.0553  -50.0000   90.0000 39

#__ type_ start__ end____ width___ exp.time_
 10 omega   88.00  115.00   1.0000    9.6600
omega____ theta____ kappa____ phi______ frames
    -      110.0553 -111.0000 -150.0000 27

#__ type_ start__ end____ width___ exp.time_
 11 omega  146.00  174.00   1.0000    9.6600
omega____ theta____ kappa____ phi______ frames
    -      110.0553  111.0000 -150.0000 28

#__ type_ start__ end____ width___ exp.time_
 12 omega   84.00  116.00   1.0000    9.6600
omega____ theta____ kappa____ phi______ frames
    -      110.0553 -111.0000   60.0000 32

#__ type_ start__ end____ width___ exp.time_
 13 omega   42.00   93.00   1.0000    9.6600
omega____ theta____ kappa____ phi______ frames
    -      110.0553  -25.0000   60.0000 51

#__ type_ start__ end____ width___ exp.time_
 14 omega   37.00   91.00   1.0000    9.6600
omega____ theta____ kappa____ phi______ frames
    -      110.0553  -25.0000 -180.0000 54

#__ type_ start__ end____ width___ exp.time_
 15 omega   48.00   93.00   1.0000    9.6600
omega____ theta____ kappa____ phi______ frames
    -      110.0553  -38.0000  -60.0000 45

#__ type_ start__ end____ width___ exp.time_
 16 omega   38.00   85.00   1.0000    9.6600
omega____ theta____ kappa____ phi______ frames
    -      110.0553  -38.0000   30.0000 47

#__ type_ start__ end____ width___ exp.time_
 17 omega   41.00  136.00   1.0000    9.6600
omega____ theta____ kappa____ phi______ frames
    -      110.0553  -77.0000  -60.0000 95

#__ type_ start__ end____ width___ exp.time_
 18 omega  149.00  176.00   1.0000    9.6600
omega____ theta____ kappa____ phi______ frames
    -      110.0553  111.0000  -60.0000 27

#__ type_ start__ end____ width___ exp.time_
 19 omega   50.00   92.00   1.0000    9.6600
omega____ theta____ kappa____ phi______ frames
    -      110.0553  -38.0000  120.0000 42

#__ type_ start__ end____ width___ exp.time_
 20 omega   53.00  123.00   1.0000    9.6600
omega____ theta____ kappa____ phi______ frames
    -      110.0553  -92.0000 -150.0000 70

#__ type_ start__ end____ width___ exp.time_
 21 omega   84.00  165.00   1.0000    9.6600
omega____ theta____ kappa____ phi______ frames
    -      110.0553   25.0000   90.0000 81

#__ type_ start__ end____ width___ exp.time_
 22 omega   44.00   92.00   1.0000    9.6600
omega____ theta____ kappa____ phi______ frames
    -      110.0553  -25.0000  -90.0000 48

#__ type_ start__ end____ width___ exp.time_
 23 omega   45.00  104.00   1.0000    9.6600
omega____ theta____ kappa____ phi______ frames
    -      110.0553  -50.0000 -180.0000 59

#__ type_ start__ end____ width___ exp.time_
 24 omega   38.00   79.00   1.0000    9.6600
omega____ theta____ kappa____ phi______ frames
    -      110.0553  -25.0000 -120.0000 41

#__ type_ start__ end____ width___ exp.time_
 25 omega   87.00  155.00   1.0000    9.6600
omega____ theta____ kappa____ phi______ frames
    -      110.0553   25.0000 -150.0000 68
;
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.1506829000
_diffrn_orient_matrix_UB_12      -0.0554490000
_diffrn_orient_matrix_UB_13      -0.0567297000
_diffrn_orient_matrix_UB_21      -0.0171635000
_diffrn_orient_matrix_UB_22      -0.1827087000
_diffrn_orient_matrix_UB_23      0.0202518000
_diffrn_orient_matrix_UB_31      -0.2815819000
_diffrn_orient_matrix_UB_32      0.0232171000
_diffrn_orient_matrix_UB_33      -0.0291379000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Enhance (Cu) X-ray Source'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                2887
_reflns_number_total             3455
_reflns_odcompleteness_completeness 99.72
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_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         0.485
_refine_diff_density_min         -0.225
_refine_diff_density_rms         0.057
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     196
_refine_ls_number_reflns         3455
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0641
_refine_ls_R_factor_gt           0.0549
_refine_ls_restrained_S_all      1.044
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.1046P)²+0.0180P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1482
_refine_ls_wR_factor_ref         0.1599
_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:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B), C9(H9A,H9B), C11(H11A,H11B), C12(H12A,H12B), C13(H13A,H13B),
 C14(H14A,H14B), C15(H15A,H15B), C16(H16A,H16B), C17(H17A,H17B), C18(H18A,H18B),
  C19(H19A,H19B)
2.b Aromatic/amide H refined with riding coordinates:
 C7(H7)
2.c Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C), C(HA,HB,HC)
;
_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_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_refinement_flags_posn
S1 S 0.68698(10) 0.18068(6) 0.49898(2) 0.0471(2) Uani 1 d . . .
O O 0.6209(3) 0.2940(2) 0.38420(6) 0.0603(4) Uani 1 d . . .
N2 N 0.2683(3) 0.4028(2) 0.44346(7) 0.0443(4) Uani 1 d . . .
N3 N 0.2534(3) 0.3548(2) 0.54462(7) 0.0458(4) Uani 1 d . . .
C4 C 0.3795(4) 0.3251(2) 0.49500(8) 0.0398(4) Uani 1 d . . .
C5 C 0.3936(4) 0.3812(3) 0.39035(8) 0.0460(4) Uani 1 d . . .
C6 C 0.6377(4) 0.1557(3) 0.57364(8) 0.0454(4) Uani 1 d . . .
C7 C 0.4032(4) 0.2574(3) 0.58890(8) 0.0468(4) Uani 1 d . . .
H7 H 0.3438 0.2623 0.6276 0.056 Uiso 1 calc . . R
C8 C 0.2188(5) 0.4681(3) 0.34018(9) 0.0569(6) Uani 1 d . . .
H8A H 0.0896 0.3987 0.3319 0.068 Uiso 1 calc . . R
H8B H 0.1109 0.5723 0.3518 0.068 Uiso 1 calc . . R
C9 C 0.3851(5) 0.5046(3) 0.28534(9) 0.0573(5) Uani 1 d . . .
H9A H 0.4832 0.5932 0.2910 0.069 Uiso 1 calc . . R
H9B H 0.5227 0.4059 0.2785 0.069 Uiso 1 calc . . R
C10 C 0.8357(5) 0.0341(3) 0.61170(10) 0.0586(6) Uani 1 d . . .
H10A H 0.8218 -0.0777 0.6054 0.088 Uiso 1 calc . . GR
H10B H 0.7904 0.0518 0.6517 0.088 Uiso 1 calc . . GR
H10C H 1.0218 0.0505 0.6024 0.088 Uiso 1 calc . . GR
C11 C 0.3584(6) 0.6990(4) 0.06976(10) 0.0648(6) Uani 1 d . . .
H11A H 0.4177 0.8013 0.0765 0.078 Uiso 1 calc . . R
H11B H 0.5240 0.6155 0.0638 0.078 Uiso 1 calc . . R
C12 C 0.2028(6) 0.6412(4) 0.12361(10) 0.0657(6) Uani 1 d . . .
H12A H 0.0407 0.7264 0.1304 0.079 Uiso 1 calc . . R
H12B H 0.1380 0.5409 0.1165 0.079 Uiso 1 calc . . R
C13 C 0.3703(5) 0.6048(4) 0.17780(10) 0.0627(6) Uani 1 d . . .
H13A H 0.4438 0.7031 0.1837 0.075 Uiso 1 calc . . R
H13B H 0.5269 0.5152 0.1718 0.075 Uiso 1 calc . . R
C14 C 0.3504(6) 0.7922(4) -0.03828(10) 0.0677(7) Uani 1 d . . .
H14A H 0.4025 0.8962 -0.0311 0.081 Uiso 1 calc . . R
H14B H 0.5201 0.7118 -0.0441 0.081 Uiso 1 calc . . R
C15 C 0.2107(5) 0.5559(4) 0.23234(9) 0.0618(6) Uani 1 d . . .
H15A H 0.0646 0.6494 0.2404 0.074 Uiso 1 calc . . R
H15B H 0.1230 0.4640 0.2252 0.074 Uiso 1 calc . . R
C16 C 0.1956(6) 0.7300(4) 0.01506(10) 0.0679(7) Uani 1 d . . .
H16A H 0.0275 0.8113 0.0213 0.081 Uiso 1 calc . . R
H16B H 0.1407 0.6269 0.0077 0.081 Uiso 1 calc . . R
C17 C 0.3459(6) 0.8855(4) -0.14641(10) 0.0689(7) Uani 1 d . . .
H17A H 0.3912 0.9912 -0.1391 0.083 Uiso 1 calc . . R
H17B H 0.5193 0.8076 -0.1515 0.083 Uiso 1 calc . . R
C18 C 0.1901(6) 0.8208(4) -0.09355(10) 0.0675(7) Uani 1 d . . .
H18A H 0.0191 0.9001 -0.0877 0.081 Uiso 1 calc . . R
H18B H 0.1405 0.7164 -0.1012 0.081 Uiso 1 calc . . R
C19 C 0.1913(7) 0.9102(5) -0.20202(11) 0.0789(8) Uani 1 d . . .
H19A H 0.0175 0.9879 -0.1971 0.095 Uiso 1 calc . . R
H19B H 0.1474 0.8044 -0.2098 0.095 Uiso 1 calc . . R
C C 0.3533(8) 0.9760(5) -0.25380(12) 0.0955(11) Uani 1 d . . .
HA H 0.2445 0.9899 -0.2878 0.143 Uiso 1 calc . . GR
HB H 0.5232 0.8981 -0.2596 0.143 Uiso 1 calc . . GR
HC H 0.3948 1.0816 -0.2467 0.143 Uiso 1 calc . . GR
H2 H 0.120(5) 0.463(3) 0.4457(11) 0.051(7) Uiso 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 C4 1.7287(19) . ?
S1 C6 1.730(2) . ?
O C5 1.213(3) . ?
N2 C4 1.379(2) . ?
N2 C5 1.359(2) . ?
N3 C4 1.300(2) . ?
N3 C7 1.382(3) . ?
C5 C8 1.513(3) . ?
C6 C7 1.339(3) . ?
C6 C10 1.499(3) . ?
C8 C9 1.510(3) . ?
C9 C15 1.510(3) . ?
C11 C12 1.511(3) . ?
C11 C16 1.506(3) . ?
C12 C13 1.508(3) . ?
C13 C15 1.512(3) . ?
C14 C16 1.513(3) . ?
C14 C18 1.511(3) . ?
C17 C18 1.514(3) . ?
C17 C19 1.505(3) . ?
C19 C 1.516(4) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C4 S1 C6 89.07(9) . . ?
C5 N2 C4 124.11(17) . . ?
C4 N3 C7 109.57(17) . . ?
N2 C4 S1 123.60(14) . . ?
N3 C4 S1 115.16(14) . . ?
N3 C4 N2 121.23(17) . . ?
O C5 N2 122.39(19) . . ?
O C5 C8 123.50(18) . . ?
N2 C5 C8 114.04(17) . . ?
C7 C6 S1 109.17(15) . . ?
C7 C6 C10 128.67(19) . . ?
C10 C6 S1 122.15(16) . . ?
C6 C7 N3 117.02(17) . . ?
C9 C8 C5 113.98(18) . . ?
C15 C9 C8 113.61(19) . . ?
C16 C11 C12 114.9(2) . . ?
C13 C12 C11 114.6(2) . . ?
C12 C13 C15 114.7(2) . . ?
C18 C14 C16 114.8(2) . . ?
C9 C15 C13 114.4(2) . . ?
C11 C16 C14 114.5(2) . . ?
C19 C17 C18 114.8(2) . . ?
C14 C18 C17 114.3(2) . . ?
C17 C19 C 113.2(3) . . ?

_database_code_depnum_ccdc_archive 'CCDC 965887'
_olex2_submission_special_instructions 'No special instructions were received'
