# Electronic Supplementary Material (ESI) for Chemical Communications.
# This journal is © The Royal Society of Chemistry 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_sh_906
_audit_creation_date             2013-09-13
_audit_creation_method           
;
  Olex2 1.2
  (compiled Apr 23 2013 17:54:37, GUI svn.r4466)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C27 H27 N O4 S'
_chemical_formula_sum            'C27 H27 N O4 S'
_chemical_formula_weight         461.56
_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      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                   8.4189(12)
_cell_length_b                   10.2968(8)
_cell_length_c                   14.6301(19)
_cell_angle_alpha                70.264(10)
_cell_angle_beta                 86.034(11)
_cell_angle_gamma                81.468(9)
_cell_volume                     1180.3(2)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    2795
_cell_measurement_temperature    293.89(10)
_cell_measurement_theta_max      26.2260
_cell_measurement_theta_min      3.6500
_exptl_absorpt_coefficient_mu    0.171
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.66807
_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_density_diffrn    1.299
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             488
_exptl_crystal_size_max          0.3700
_exptl_crystal_size_mid          0.3500
_exptl_crystal_size_min          0.2400
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0365
_diffrn_reflns_av_unetI/netI     0.0577
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            8762
_diffrn_reflns_theta_full        25.50
_diffrn_reflns_theta_max         26.02
_diffrn_reflns_theta_min         2.96
_diffrn_ambient_temperature      293.89(10)
_diffrn_detector_area_resol_mean 16.0733
_diffrn_measured_fraction_theta_full 0.9785
_diffrn_measured_fraction_theta_max 0.8746
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -73.00  -34.00   1.5000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      -19.5262  130.0000  179.0000 26

#__ type_ start__ end____ width___ exp.time_
  2 omega  -18.00   24.00   1.5000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      -19.5262  -99.0000  -60.0000 28

#__ type_ start__ end____ width___ exp.time_
  3 omega   43.00  104.50   1.5000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       22.8075  178.0000 -180.0000 41

#__ type_ start__ end____ width___ exp.time_
  4 omega  -10.00   98.00   1.5000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       22.8075   19.0000 -120.0000 72

#__ type_ start__ end____ width___ exp.time_
  5 omega  -75.00  -48.00   1.5000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -19.5262  132.0000  178.0000 18

#__ type_ start__ end____ width___ exp.time_
  6 omega  -62.00  -35.00   1.5000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -19.5262   91.0000   81.7543 18

#__ type_ start__ end____ width___ exp.time_
  7 omega   50.00   87.50   1.5000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       22.8075  178.0000    0.0000 25

#__ type_ start__ end____ width___ exp.time_
  8 omega  -54.00   58.50   1.5000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       22.8075  -19.0000 -120.0000 75
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0487203000
_diffrn_orient_matrix_UB_12      0.0332458000
_diffrn_orient_matrix_UB_13      -0.0413142000
_diffrn_orient_matrix_UB_21      -0.0675075000
_diffrn_orient_matrix_UB_22      0.0061629000
_diffrn_orient_matrix_UB_23      0.0307685000
_diffrn_orient_matrix_UB_31      0.0182088000
_diffrn_orient_matrix_UB_32      0.0656508000
_diffrn_orient_matrix_UB_33      -0.0012357000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                3071
_reflns_number_total             4562
_reflns_odcompleteness_completeness 97.85
_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    
;
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         0.199
_refine_diff_density_min         -0.429
_refine_diff_density_rms         0.042
_refine_ls_extinction_coef       0.0086(19)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     300
_refine_ls_number_reflns         4562
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0825
_refine_ls_R_factor_gt           0.0520
_refine_ls_restrained_S_all      1.050
_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)+(0.0570P)²+0.1896P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1228
_refine_ls_wR_factor_ref         0.1494
_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 Ternary CH refined with riding coordinates:
 C9(H9), C12(H12)
2.b Secondary CH2 refined with riding coordinates:
 C13(H13A,H13B), C14(H14A,H14B), C15(H15A,H15B), C17(H17A,H17B), C18(H18A,
 H18B), C19(H19A,H19B)
2.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C8(H8), C22(H22), C23(H23), C25(H25), C26(H26)
2.d Idealised Me refined as rotating group:
 C27(H27A,H27B,H27C)
2.e :
 C11(H11)
;
_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 0.03755(8) 0.86522(6) 0.23081(6) 0.0546(2) Uani 1 1 d . . .
O1 O -0.0874(2) 0.89922(18) 0.16202(16) 0.0707(6) Uani 1 1 d . . .
O2 O 0.0047(3) 0.87026(19) 0.32615(15) 0.0708(6) Uani 1 1 d . . .
O3 O 0.7566(2) 0.43951(17) 0.45285(12) 0.0535(5) Uani 1 1 d . . .
O4 O 0.6860(3) 0.17906(19) 0.52547(14) 0.0679(6) Uani 1 1 d . . .
N1 N 0.1171(2) 0.70207(19) 0.24563(15) 0.0472(5) Uani 1 1 d . . .
C1 C 0.1474(3) 0.6424(2) 0.17132(18) 0.0446(6) Uani 1 1 d . . .
C2 C 0.0743(3) 0.6755(3) 0.0828(2) 0.0585(8) Uani 1 1 d . . .
H2 H -0.0069 0.7503 0.0624 0.070 Uiso 1 1 calc R . .
C3 C 0.1261(4) 0.5937(3) 0.0262(2) 0.0670(9) Uani 1 1 d . . .
H3 H 0.0806 0.6145 -0.0341 0.080 Uiso 1 1 calc R . .
C4 C 0.2447(4) 0.4811(3) 0.0578(2) 0.0692(9) Uani 1 1 d . . .
H4 H 0.2773 0.4273 0.0184 0.083 Uiso 1 1 calc R . .
C5 C 0.3154(4) 0.4472(3) 0.1461(2) 0.0570(7) Uani 1 1 d . . .
H5 H 0.3933 0.3700 0.1669 0.068 Uiso 1 1 calc R . .
C6 C 0.2695(3) 0.5293(2) 0.20414(18) 0.0441(6) Uani 1 1 d . . .
C7 C 0.3182(3) 0.5242(2) 0.29848(17) 0.0425(6) Uani 1 1 d . . .
C8 C 0.2269(3) 0.6290(2) 0.32039(18) 0.0441(6) Uani 1 1 d . . .
H8 H 0.2350 0.6503 0.3767 0.053 Uiso 1 1 calc R . .
C9 C 0.4490(3) 0.4234(2) 0.35972(18) 0.0424(6) Uani 1 1 d . . .
H9 H 0.4492 0.4425 0.4209 0.051 Uiso 1 1 calc R . .
C10 C 0.4100(3) 0.2800(3) 0.38315(18) 0.0499(6) Uani 1 1 d . . .
C11 C 0.3768(4) 0.1684(3) 0.4007(2) 0.0677(9) Uani 1 1 d . . .
H11 H 0.3502 0.0791 0.4148 0.081 Uiso 1 1 calc R . .
C12 C 0.6194(3) 0.4410(2) 0.31082(18) 0.0465(6) Uani 1 1 d . . .
H12 H 0.6307 0.3980 0.2599 0.056 Uiso 1 1 calc R . .
C13 C 0.6428(3) 0.5952(3) 0.2637(2) 0.0621(8) Uani 1 1 d . . .
H13A H 0.7395 0.6020 0.2232 0.075 Uiso 1 1 calc R . .
H13B H 0.5526 0.6443 0.2223 0.075 Uiso 1 1 calc R . .
C14 C 0.6560(4) 0.6640(3) 0.3396(2) 0.0693(9) Uani 1 1 d . . .
H14A H 0.6810 0.7580 0.3079 0.083 Uiso 1 1 calc R . .
H14B H 0.5541 0.6692 0.3743 0.083 Uiso 1 1 calc R . .
C15 C 0.7849(4) 0.5818(3) 0.4097(2) 0.0651(8) Uani 1 1 d . . .
H15A H 0.8884 0.5853 0.3761 0.078 Uiso 1 1 calc R . .
H15B H 0.7876 0.6228 0.4603 0.078 Uiso 1 1 calc R . .
C16 C 0.7571(3) 0.3693(2) 0.38434(18) 0.0460(6) Uani 1 1 d . . .
C17 C 0.9191(3) 0.3500(3) 0.3327(2) 0.0653(8) Uani 1 1 d . . .
H17A H 0.9297 0.4294 0.2746 0.078 Uiso 1 1 calc R . .
H17B H 1.0073 0.3386 0.3752 0.078 Uiso 1 1 calc R . .
C18 C 0.9169(4) 0.2179(3) 0.3069(3) 0.0847(10) Uani 1 1 d . . .
H18A H 0.8628 0.2395 0.2461 0.102 Uiso 1 1 calc R . .
H18B H 1.0253 0.1736 0.3012 0.102 Uiso 1 1 calc R . .
C19 C 0.8256(4) 0.1242(3) 0.3904(3) 0.0826(10) Uani 1 1 d . . .
H19A H 0.7483 0.0834 0.3661 0.099 Uiso 1 1 calc R . .
H19B H 0.8989 0.0499 0.4326 0.099 Uiso 1 1 calc R . .
C20 C 0.7416(3) 0.2169(3) 0.4444(2) 0.0518(7) Uani 1 1 d . . .
C21 C 0.1937(3) 0.9625(2) 0.17830(19) 0.0456(6) Uani 1 1 d . . .
C22 C 0.2001(4) 1.0294(3) 0.0798(2) 0.0584(7) Uani 1 1 d . . .
H22 H 0.1194 1.0259 0.0407 0.070 Uiso 1 1 calc R . .
C23 C 0.3271(4) 1.1017(3) 0.0393(2) 0.0649(8) Uani 1 1 d . . .
H23 H 0.3306 1.1471 -0.0275 0.078 Uiso 1 1 calc R . .
C24 C 0.4480(4) 1.1085(2) 0.0945(2) 0.0574(7) Uani 1 1 d . . .
C25 C 0.4405(4) 1.0395(3) 0.1938(2) 0.0688(9) Uani 1 1 d . . .
H25 H 0.5218 1.0425 0.2326 0.083 Uiso 1 1 calc R . .
C26 C 0.3150(4) 0.9669(3) 0.2358(2) 0.0631(8) Uani 1 1 d . . .
H26 H 0.3116 0.9210 0.3025 0.076 Uiso 1 1 calc R . .
C27 C 0.5870(4) 1.1876(3) 0.0512(3) 0.0827(10) Uani 1 1 d . . .
H27A H 0.5728 1.2736 0.0647 0.124 Uiso 1 1 calc R . .
H27B H 0.5916 1.2068 -0.0178 0.124 Uiso 1 1 calc R . .
H27C H 0.6853 1.1328 0.0790 0.124 Uiso 1 1 calc R . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 O1 1.4288(19) . ?
S1 O2 1.420(2) . ?
S1 N1 1.661(2) . ?
S1 C21 1.747(3) . ?
O3 C15 1.435(3) . ?
O3 C16 1.420(3) . ?
O4 C20 1.201(3) . ?
N1 C1 1.411(3) . ?
N1 C8 1.412(3) . ?
C1 C2 1.387(3) . ?
C1 C6 1.407(3) . ?
C2 H2 0.9300 . ?
C2 C3 1.377(4) . ?
C3 H3 0.9300 . ?
C3 C4 1.383(4) . ?
C4 H4 0.9300 . ?
C4 C5 1.373(4) . ?
C5 H5 0.9300 . ?
C5 C6 1.388(4) . ?
C6 C7 1.448(3) . ?
C7 C8 1.346(3) . ?
C7 C9 1.504(3) . ?
C8 H8 0.9300 . ?
C9 H9 0.9800 . ?
C9 C10 1.481(3) . ?
C9 C12 1.566(3) . ?
C10 C11 1.162(3) . ?
C11 H11 0.9300 . ?
C12 H12 0.9800 . ?
C12 C13 1.539(3) . ?
C12 C16 1.558(3) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C13 C14 1.522(4) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C14 C15 1.498(4) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C16 C17 1.533(4) . ?
C16 C20 1.538(3) . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C17 C18 1.532(4) . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C18 C19 1.519(5) . ?
C19 H19A 0.9700 . ?
C19 H19B 0.9700 . ?
C19 C20 1.505(4) . ?
C21 C22 1.373(4) . ?
C21 C26 1.382(3) . ?
C22 H22 0.9300 . ?
C22 C23 1.378(4) . ?
C23 H23 0.9300 . ?
C23 C24 1.366(4) . ?
C24 C25 1.387(4) . ?
C24 C27 1.505(4) . ?
C25 H25 0.9300 . ?
C25 C26 1.374(4) . ?
C26 H26 0.9300 . ?
C27 H27A 0.9600 . ?
C27 H27B 0.9600 . ?
C27 H27C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 S1 N1 106.64(11) . . ?
O1 S1 C21 109.04(12) . . ?
O2 S1 O1 121.22(14) . . ?
O2 S1 N1 105.32(11) . . ?
O2 S1 C21 109.18(12) . . ?
N1 S1 C21 104.04(11) . . ?
C16 O3 C15 113.43(19) . . ?
C1 N1 S1 125.72(16) . . ?
C1 N1 C8 107.7(2) . . ?
C8 N1 S1 120.88(16) . . ?
C2 C1 N1 130.8(2) . . ?
C2 C1 C6 122.3(3) . . ?
C6 C1 N1 106.9(2) . . ?
C1 C2 H2 121.2 . . ?
C3 C2 C1 117.6(3) . . ?
C3 C2 H2 121.2 . . ?
C2 C3 H3 119.5 . . ?
C2 C3 C4 120.9(3) . . ?
C4 C3 H3 119.5 . . ?
C3 C4 H4 119.3 . . ?
C5 C4 C3 121.4(3) . . ?
C5 C4 H4 119.3 . . ?
C4 C5 H5 120.3 . . ?
C4 C5 C6 119.4(3) . . ?
C6 C5 H5 120.3 . . ?
C1 C6 C7 107.9(2) . . ?
C5 C6 C1 118.4(2) . . ?
C5 C6 C7 133.7(2) . . ?
C6 C7 C9 126.7(2) . . ?
C8 C7 C6 107.1(2) . . ?
C8 C7 C9 126.1(2) . . ?
N1 C8 H8 124.9 . . ?
C7 C8 N1 110.3(2) . . ?
C7 C8 H8 124.9 . . ?
C7 C9 H9 107.6 . . ?
C7 C9 C12 112.47(18) . . ?
C10 C9 C7 109.04(18) . . ?
C10 C9 H9 107.6 . . ?
C10 C9 C12 112.3(2) . . ?
C12 C9 H9 107.6 . . ?
C11 C10 C9 178.8(3) . . ?
C10 C11 H11 180.0 . . ?
C9 C12 H12 108.2 . . ?
C13 C12 C9 112.0(2) . . ?
C13 C12 H12 108.2 . . ?
C13 C12 C16 107.66(19) . . ?
C16 C12 C9 112.33(19) . . ?
C16 C12 H12 108.2 . . ?
C12 C13 H13A 109.3 . . ?
C12 C13 H13B 109.3 . . ?
H13A C13 H13B 107.9 . . ?
C14 C13 C12 111.7(2) . . ?
C14 C13 H13A 109.3 . . ?
C14 C13 H13B 109.3 . . ?
C13 C14 H14A 109.7 . . ?
C13 C14 H14B 109.7 . . ?
H14A C14 H14B 108.2 . . ?
C15 C14 C13 110.0(3) . . ?
C15 C14 H14A 109.7 . . ?
C15 C14 H14B 109.7 . . ?
O3 C15 C14 110.8(2) . . ?
O3 C15 H15A 109.5 . . ?
O3 C15 H15B 109.5 . . ?
C14 C15 H15A 109.5 . . ?
C14 C15 H15B 109.5 . . ?
H15A C15 H15B 108.1 . . ?
O3 C16 C12 110.0(2) . . ?
O3 C16 C17 114.9(2) . . ?
O3 C16 C20 105.7(2) . . ?
C17 C16 C12 111.8(2) . . ?
C17 C16 C20 100.1(2) . . ?
C20 C16 C12 113.89(18) . . ?
C16 C17 H17A 110.8 . . ?
C16 C17 H17B 110.8 . . ?
H17A C17 H17B 108.9 . . ?
C18 C17 C16 104.6(2) . . ?
C18 C17 H17A 110.8 . . ?
C18 C17 H17B 110.8 . . ?
C17 C18 H18A 110.7 . . ?
C17 C18 H18B 110.7 . . ?
H18A C18 H18B 108.8 . . ?
C19 C18 C17 105.0(3) . . ?
C19 C18 H18A 110.7 . . ?
C19 C18 H18B 110.7 . . ?
C18 C19 H19A 110.6 . . ?
C18 C19 H19B 110.6 . . ?
H19A C19 H19B 108.7 . . ?
C20 C19 C18 105.6(3) . . ?
C20 C19 H19A 110.6 . . ?
C20 C19 H19B 110.6 . . ?
O4 C20 C16 124.6(3) . . ?
O4 C20 C19 126.1(3) . . ?
C19 C20 C16 108.9(3) . . ?
C22 C21 S1 120.3(2) . . ?
C22 C21 C26 119.9(3) . . ?
C26 C21 S1 119.7(2) . . ?
C21 C22 H22 120.3 . . ?
C21 C22 C23 119.5(3) . . ?
C23 C22 H22 120.3 . . ?
C22 C23 H23 119.1 . . ?
C24 C23 C22 121.8(3) . . ?
C24 C23 H23 119.1 . . ?
C23 C24 C25 118.0(3) . . ?
C23 C24 C27 122.3(3) . . ?
C25 C24 C27 119.6(3) . . ?
C24 C25 H25 119.4 . . ?
C26 C25 C24 121.2(3) . . ?
C26 C25 H25 119.4 . . ?
C21 C26 H26 120.2 . . ?
C25 C26 C21 119.6(3) . . ?
C25 C26 H26 120.2 . . ?
C24 C27 H27A 109.5 . . ?
C24 C27 H27B 109.5 . . ?
C24 C27 H27C 109.5 . . ?
H27A C27 H27B 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
S1 N1 C1 C2 -26.6(4) . . . . ?
S1 N1 C1 C6 156.17(17) . . . . ?
S1 N1 C8 C7 -157.40(17) . . . . ?
S1 C21 C22 C23 -177.8(2) . . . . ?
S1 C21 C26 C25 177.8(2) . . . . ?
O1 S1 N1 C1 40.2(2) . . . . ?
O1 S1 N1 C8 -169.90(19) . . . . ?
O1 S1 C21 C22 -14.5(3) . . . . ?
O1 S1 C21 C26 168.3(2) . . . . ?
O2 S1 N1 C1 170.2(2) . . . . ?
O2 S1 N1 C8 -39.9(2) . . . . ?
O2 S1 C21 C22 -149.0(2) . . . . ?
O2 S1 C21 C26 33.9(2) . . . . ?
O3 C16 C17 C18 152.0(2) . . . . ?
O3 C16 C20 O4 22.8(3) . . . . ?
O3 C16 C20 C19 -150.1(2) . . . . ?
N1 S1 C21 C22 99.0(2) . . . . ?
N1 S1 C21 C26 -78.2(2) . . . . ?
N1 C1 C2 C3 -177.3(2) . . . . ?
N1 C1 C6 C5 176.3(2) . . . . ?
N1 C1 C6 C7 -2.3(2) . . . . ?
C1 N1 C8 C7 -2.7(3) . . . . ?
C1 C2 C3 C4 1.2(4) . . . . ?
C1 C6 C7 C8 0.7(3) . . . . ?
C1 C6 C7 C9 -177.8(2) . . . . ?
C2 C1 C6 C5 -1.2(4) . . . . ?
C2 C1 C6 C7 -179.8(2) . . . . ?
C2 C3 C4 C5 -0.3(5) . . . . ?
C3 C4 C5 C6 -1.4(4) . . . . ?
C4 C5 C6 C1 2.1(4) . . . . ?
C4 C5 C6 C7 -179.8(3) . . . . ?
C5 C6 C7 C8 -177.6(3) . . . . ?
C5 C6 C7 C9 3.9(4) . . . . ?
C6 C1 C2 C3 -0.5(4) . . . . ?
C6 C7 C8 N1 1.2(3) . . . . ?
C6 C7 C9 C10 -60.3(3) . . . . ?
C6 C7 C9 C12 64.9(3) . . . . ?
C7 C9 C10 C11 -5(15) . . . . ?
C7 C9 C12 C13 42.2(3) . . . . ?
C7 C9 C12 C16 163.51(19) . . . . ?
C8 N1 C1 C2 -179.8(2) . . . . ?
C8 N1 C1 C6 3.0(2) . . . . ?
C8 C7 C9 C10 121.4(3) . . . . ?
C8 C7 C9 C12 -113.4(3) . . . . ?
C9 C7 C8 N1 179.8(2) . . . . ?
C9 C12 C13 C14 70.6(3) . . . . ?
C9 C12 C16 O3 -67.5(2) . . . . ?
C9 C12 C16 C17 163.6(2) . . . . ?
C9 C12 C16 C20 51.0(3) . . . . ?
C10 C9 C12 C13 165.6(2) . . . . ?
C10 C9 C12 C16 -73.1(3) . . . . ?
C12 C9 C10 C11 -131(15) . . . . ?
C12 C13 C14 C15 53.8(3) . . . . ?
C12 C16 C17 C18 -81.7(3) . . . . ?
C12 C16 C20 O4 -98.1(3) . . . . ?
C12 C16 C20 C19 89.0(3) . . . . ?
C13 C12 C16 O3 56.3(3) . . . . ?
C13 C12 C16 C17 -72.7(3) . . . . ?
C13 C12 C16 C20 174.8(2) . . . . ?
C13 C14 C15 O3 -55.3(3) . . . . ?
C15 O3 C16 C12 -62.0(3) . . . . ?
C15 O3 C16 C17 65.3(3) . . . . ?
C15 O3 C16 C20 174.6(2) . . . . ?
C16 O3 C15 C14 61.5(3) . . . . ?
C16 C12 C13 C14 -53.4(3) . . . . ?
C16 C17 C18 C19 -34.9(3) . . . . ?
C17 C16 C20 O4 142.5(3) . . . . ?
C17 C16 C20 C19 -30.4(3) . . . . ?
C17 C18 C19 C20 15.2(4) . . . . ?
C18 C19 C20 O4 -162.9(3) . . . . ?
C18 C19 C20 C16 9.9(3) . . . . ?
C20 C16 C17 C18 39.2(3) . . . . ?
C21 S1 N1 C1 -75.0(2) . . . . ?
C21 S1 N1 C8 74.9(2) . . . . ?
C21 C22 C23 C24 0.3(5) . . . . ?
C22 C21 C26 C25 0.6(4) . . . . ?
C22 C23 C24 C25 0.2(4) . . . . ?
C22 C23 C24 C27 -179.8(3) . . . . ?
C23 C24 C25 C26 -0.3(5) . . . . ?
C24 C25 C26 C21 -0.1(5) . . . . ?
C26 C21 C22 C23 -0.7(4) . . . . ?
C27 C24 C25 C26 179.7(3) . . . . ?

_database_code_depnum_ccdc_archive 'CCDC 973585'
#######################################################################
#
#                 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_dcm-sh
_audit_creation_date             2013-09-13
_audit_creation_method           
;
  Olex2 1.2
  (compiled Apr 23 2013 17:54:37, GUI svn.r4466)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C24 H25 N O3 S'
_chemical_formula_sum            'C24 H24 N O3 S'
_chemical_formula_weight         406.50
_chemical_absolute_configuration ?
_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           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                   6.4601(16)
_cell_length_b                   12.695(3)
_cell_length_c                   13.331(2)
_cell_angle_alpha                90
_cell_angle_beta                 100.56(2)
_cell_angle_gamma                90
_cell_volume                     1074.8(4)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    600
_cell_measurement_temperature    294.68(10)
_cell_measurement_theta_max      19.5870
_cell_measurement_theta_min      3.4720
_exptl_absorpt_coefficient_mu    0.175
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.19983
_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_density_diffrn    1.256
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             430
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.13
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0695
_diffrn_reflns_av_unetI/netI     0.1545
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.876
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            4271
_diffrn_reflns_point_group_measured_fraction_full 0.701
_diffrn_reflns_point_group_measured_fraction_max 0.595
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.548
_diffrn_reflns_theta_min         3.208
_diffrn_ambient_temperature      294.68(10)
_diffrn_detector_area_resol_mean 16.0733
_diffrn_measured_fraction_theta_full 0.9900
_diffrn_measured_fraction_theta_max 0.5942
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -15.00   19.50   1.5000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      -19.3700  -99.0000   30.0000 23

#__ type_ start__ end____ width___ exp.time_
  2 omega   41.00  101.00   1.5000   16.0000
omega____ theta____ kappa____ phi______ frames
    -       22.6512  178.0000    0.0000 40

#__ type_ start__ end____ width___ exp.time_
  3 omega  -27.00    0.00   1.5000   16.0000
omega____ theta____ kappa____ phi______ frames
    -       22.6512  -57.0000 -180.0000 18

#__ type_ start__ end____ width___ exp.time_
  4 omega   -8.00   97.00   1.5000   16.0000
omega____ theta____ kappa____ phi______ frames
    -       22.6512   38.0000  120.0000 70
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0264609000
_diffrn_orient_matrix_UB_12      0.0503596000
_diffrn_orient_matrix_UB_13      -0.0214071000
_diffrn_orient_matrix_UB_21      0.0939007000
_diffrn_orient_matrix_UB_22      0.0211464000
_diffrn_orient_matrix_UB_23      0.0290281000
_diffrn_orient_matrix_UB_31      0.0543006000
_diffrn_orient_matrix_UB_32      -0.0116015000
_diffrn_orient_matrix_UB_33      -0.0404001000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_reflns_Friedel_coverage         0.302
_reflns_Friedel_fraction_full    0.379
_reflns_Friedel_fraction_max     0.288
_reflns_number_gt                1349
_reflns_number_total             3253
_reflns_odcompleteness_completeness 99.00
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (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    
;
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         0.277
_refine_diff_density_min         -0.274
_refine_diff_density_rms         0.047
_refine_ls_abs_structure_details 
;
 Classical Flack method preferred over Parsons because s.u. lower.
;
_refine_ls_abs_structure_Flack   -0.1(2)
_refine_ls_extinction_coef       0.027(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   0.977
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     264
_refine_ls_number_reflns         3253
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.1704
_refine_ls_R_factor_gt           0.0703
_refine_ls_restrained_S_all      0.977
_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)+(0.0321P)²]
 where P=(Fo²+2Fc²)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1204
_refine_ls_wR_factor_ref         0.1754
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C8(H8), C9(H9)
2.b Secondary CH2 refined with riding coordinates:
 C10(H10A,H10B), C11(H11A,H11B), C13(H13A,H13B), C14(H14A,H14B), C15(H15A,H15B)
2.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C6(H6), C18(H18), C19(H19), C21(H21), C22(H22)
2.d Idealised Me refined as rotating group:
 C23(H23A,H23B,H23C)
2.e :
 C25(H25)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.5487(4) 0.6621(2) 0.20817(18) 0.0687(8) Uani 1 1 d . . . . .
O1 O 0.3834(10) 0.6870(6) 0.4565(5) 0.074(2) Uani 1 1 d . . . . .
O2 O 0.3522(11) 0.7133(6) 0.2161(5) 0.087(3) Uani 1 1 d . . . . .
O3 O 0.5551(13) 0.5536(6) 0.1789(5) 0.085(2) Uani 1 1 d . . . . .
N2 N 0.6957(10) 0.6711(6) 0.3205(5) 0.0551(19) Uani 1 1 d . . . . .
C2 C 1.1864(16) 0.7614(9) 0.6895(8) 0.074(3) Uani 1 1 d . . . . .
H2 H 1.2033 0.8168 0.6461 0.089 Uiso 1 1 calc R U . . .
C3 C 1.3557(19) 0.7306(12) 0.7674(9) 0.097(4) Uani 1 1 d . . . . .
H3 H 1.4826 0.7670 0.7758 0.116 Uiso 1 1 calc R U . . .
C4 C 1.334(2) 0.6480(13) 0.8301(9) 0.108(5) Uani 1 1 d . . . . .
H4 H 1.4456 0.6272 0.8803 0.130 Uiso 1 1 calc R U . . .
C5 C 1.152(2) 0.5980(11) 0.8189(10) 0.103(4) Uani 1 1 d . . . . .
H5 H 1.1373 0.5428 0.8630 0.124 Uiso 1 1 calc R U . . .
C6 C 0.9816(18) 0.6248(8) 0.7434(8) 0.078(3) Uani 1 1 d . . . . .
H6 H 0.8571 0.5865 0.7362 0.093 Uiso 1 1 calc R U . . .
C7 C 0.9979(16) 0.7092(8) 0.6784(7) 0.060(3) Uani 1 1 d . . . . .
C8 C 0.8122(14) 0.7401(7) 0.5944(6) 0.053(2) Uani 1 1 d . . . . .
H8 H 0.6942 0.6940 0.6016 0.063 Uiso 1 1 calc R U . . .
C9 C 0.8581(14) 0.7231(7) 0.4876(7) 0.050(2) Uani 1 1 d . . . . .
H9 H 0.9866 0.7624 0.4830 0.060 Uiso 1 1 calc R U . . .
C10 C 0.9002(16) 0.6065(8) 0.4666(7) 0.060(3) Uani 1 1 d . . . . .
H10A H 1.0408 0.5859 0.4996 0.072 Uiso 1 1 calc R U . . .
H10B H 0.7985 0.5611 0.4903 0.072 Uiso 1 1 calc R U . . .
C11 C 0.8766(14) 0.6018(7) 0.3501(6) 0.059(3) Uani 1 1 d . . . . .
H11A H 1.0006 0.6286 0.3272 0.071 Uiso 1 1 calc R U . . .
H11B H 0.8474 0.5308 0.3244 0.071 Uiso 1 1 calc R U . . .
C12 C 0.6850(12) 0.7575(7) 0.3948(7) 0.052(2) Uani 1 1 d . . . . .
C13 C 0.7199(14) 0.8696(7) 0.3570(8) 0.063(3) Uani 1 1 d . . . . .
H13A H 0.8180 0.9075 0.4083 0.075 Uiso 1 1 calc R U . . .
H13B H 0.7778 0.8666 0.2949 0.075 Uiso 1 1 calc R U . . .
C14 C 0.5062(18) 0.9258(9) 0.3368(9) 0.090(4) Uani 1 1 d . . . . .
H14A H 0.5221 0.9979 0.3612 0.108 Uiso 1 1 calc R U . . .
H14B H 0.4500 0.9270 0.2642 0.108 Uiso 1 1 calc R U . . .
C15 C 0.3605(17) 0.8672(8) 0.3918(9) 0.081(3) Uani 1 1 d . . . . .
H15A H 0.2236 0.8588 0.3483 0.097 Uiso 1 1 calc R U . . .
H15B H 0.3425 0.9050 0.4529 0.097 Uiso 1 1 calc R U . . .
C16 C 0.4603(15) 0.7610(8) 0.4193(7) 0.058(3) Uani 1 1 d . . . . .
C17 C 0.6577(15) 0.7349(8) 0.1180(6) 0.056(2) Uani 1 1 d . . . . .
C18 C 0.5594(18) 0.8209(9) 0.0704(8) 0.078(3) Uani 1 1 d . . . . .
H18 H 0.4285 0.8422 0.0826 0.093 Uiso 1 1 calc R U . . .
C19 C 0.6616(19) 0.8768(9) 0.0021(8) 0.078(3) Uani 1 1 d . . . . .
H19 H 0.5962 0.9373 -0.0276 0.093 Uiso 1 1 calc R U . . .
C20 C 0.8469(19) 0.8492(9) -0.0234(8) 0.072(3) Uani 1 1 d . . . . .
C21 C 0.9442(18) 0.7608(9) 0.0271(8) 0.084(3) Uani 1 1 d . . . . .
H21 H 1.0742 0.7401 0.0134 0.100 Uiso 1 1 calc R U . . .
C22 C 0.8537(17) 0.7004(9) 0.0989(7) 0.074(3) Uani 1 1 d . . . . .
H22 H 0.9210 0.6415 0.1311 0.089 Uiso 1 1 calc R U . . .
C23 C 0.950(2) 0.9070(9) -0.0961(8) 0.103(4) Uani 1 1 d . . . . .
H23A H 0.9470 0.8652 -0.1563 0.155 Uiso 1 1 calc R U . . .
H23B H 1.0937 0.9214 -0.0653 0.155 Uiso 1 1 calc R U . . .
H23C H 0.8773 0.9722 -0.1140 0.155 Uiso 1 1 calc R U . . .
C24 C 0.7459(15) 0.8496(9) 0.6108(7) 0.063(3) Uani 1 1 d . . . . .
C25 C 0.6900(18) 0.9360(9) 0.6220(9) 0.081(4) Uani 1 1 d . . . . .
H25 H 0.6457 1.0045 0.6309 0.097 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 O2 1.447(7) . ?
S1 O3 1.435(7) . ?
S1 N2 1.623(6) . ?
S1 C17 1.762(9) . ?
O1 C16 1.211(10) . ?
N2 C11 1.458(10) . ?
N2 C12 1.488(11) . ?
C2 H2 0.9300 . ?
C2 C3 1.418(13) . ?
C2 C7 1.371(12) . ?
C3 H3 0.9300 . ?
C3 C4 1.365(16) . ?
C4 H4 0.9300 . ?
C4 C5 1.318(16) . ?
C5 H5 0.9300 . ?
C5 C6 1.391(15) . ?
C6 H6 0.9300 . ?
C6 C7 1.394(12) . ?
C7 C8 1.534(12) . ?
C8 H8 0.9800 . ?
C8 C9 1.522(11) . ?
C8 C24 1.482(13) . ?
C9 H9 0.9800 . ?
C9 C10 1.539(11) . ?
C9 C12 1.570(12) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C10 C11 1.534(11) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 C13 1.540(12) . ?
C12 C16 1.546(12) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C13 C14 1.533(12) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C14 C15 1.493(13) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C15 C16 1.511(13) . ?
C17 C18 1.360(13) . ?
C17 C22 1.406(12) . ?
C18 H18 0.9300 . ?
C18 C19 1.410(13) . ?
C19 H19 0.9300 . ?
C19 C20 1.349(14) . ?
C20 C21 1.398(14) . ?
C20 C23 1.469(13) . ?
C21 H21 0.9300 . ?
C21 C22 1.432(13) . ?
C22 H22 0.9300 . ?
C23 H23A 0.9600 . ?
C23 H23B 0.9600 . ?
C23 H23C 0.9600 . ?
C24 C25 1.174(13) . ?
C25 H25 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O2 S1 N2 105.9(4) . . ?
O2 S1 C17 106.3(5) . . ?
O3 S1 O2 121.3(5) . . ?
O3 S1 N2 106.1(4) . . ?
O3 S1 C17 106.5(5) . . ?
N2 S1 C17 110.7(4) . . ?
C11 N2 S1 120.8(6) . . ?
C11 N2 C12 113.4(6) . . ?
C12 N2 S1 125.1(6) . . ?
C3 C2 H2 120.1 . . ?
C7 C2 H2 120.1 . . ?
C7 C2 C3 119.8(11) . . ?
C2 C3 H3 119.8 . . ?
C4 C3 C2 120.5(12) . . ?
C4 C3 H3 119.8 . . ?
C3 C4 H4 120.3 . . ?
C5 C4 C3 119.5(12) . . ?
C5 C4 H4 120.3 . . ?
C4 C5 H5 118.9 . . ?
C4 C5 C6 122.2(13) . . ?
C6 C5 H5 118.9 . . ?
C5 C6 H6 120.0 . . ?
C5 C6 C7 119.9(11) . . ?
C7 C6 H6 120.0 . . ?
C2 C7 C6 118.1(10) . . ?
C2 C7 C8 121.0(9) . . ?
C6 C7 C8 120.8(9) . . ?
C7 C8 H8 107.1 . . ?
C9 C8 C7 112.7(7) . . ?
C9 C8 H8 107.1 . . ?
C24 C8 C7 109.9(8) . . ?
C24 C8 H8 107.1 . . ?
C24 C8 C9 112.5(7) . . ?
C8 C9 H9 107.3 . . ?
C8 C9 C10 112.2(7) . . ?
C8 C9 C12 117.7(7) . . ?
C10 C9 H9 107.3 . . ?
C10 C9 C12 104.4(8) . . ?
C12 C9 H9 107.3 . . ?
C9 C10 H10A 111.1 . . ?
C9 C10 H10B 111.1 . . ?
H10A C10 H10B 109.0 . . ?
C11 C10 C9 103.5(7) . . ?
C11 C10 H10A 111.1 . . ?
C11 C10 H10B 111.1 . . ?
N2 C11 C10 100.2(7) . . ?
N2 C11 H11A 111.7 . . ?
N2 C11 H11B 111.7 . . ?
C10 C11 H11A 111.7 . . ?
C10 C11 H11B 111.7 . . ?
H11A C11 H11B 109.5 . . ?
N2 C12 C9 101.9(6) . . ?
N2 C12 C13 115.9(7) . . ?
N2 C12 C16 108.8(7) . . ?
C13 C12 C9 112.9(7) . . ?
C13 C12 C16 104.0(7) . . ?
C16 C12 C9 113.7(7) . . ?
C12 C13 H13A 110.1 . . ?
C12 C13 H13B 110.1 . . ?
H13A C13 H13B 108.4 . . ?
C14 C13 C12 107.9(7) . . ?
C14 C13 H13A 110.1 . . ?
C14 C13 H13B 110.1 . . ?
C13 C14 H14A 110.1 . . ?
C13 C14 H14B 110.1 . . ?
H14A C14 H14B 108.4 . . ?
C15 C14 C13 108.1(8) . . ?
C15 C14 H14A 110.1 . . ?
C15 C14 H14B 110.1 . . ?
C14 C15 H15A 110.4 . . ?
C14 C15 H15B 110.4 . . ?
C14 C15 C16 106.5(9) . . ?
H15A C15 H15B 108.6 . . ?
C16 C15 H15A 110.4 . . ?
C16 C15 H15B 110.4 . . ?
O1 C16 C12 122.4(9) . . ?
O1 C16 C15 127.1(9) . . ?
C15 C16 C12 110.5(8) . . ?
C18 C17 S1 121.9(8) . . ?
C18 C17 C22 121.6(10) . . ?
C22 C17 S1 116.5(8) . . ?
C17 C18 H18 120.9 . . ?
C17 C18 C19 118.1(11) . . ?
C19 C18 H18 120.9 . . ?
C18 C19 H19 117.5 . . ?
C20 C19 C18 125.1(11) . . ?
C20 C19 H19 117.5 . . ?
C19 C20 C21 115.3(11) . . ?
C19 C20 C23 124.6(12) . . ?
C21 C20 C23 120.0(11) . . ?
C20 C21 H21 118.3 . . ?
C20 C21 C22 123.3(11) . . ?
C22 C21 H21 118.3 . . ?
C17 C22 C21 116.5(10) . . ?
C17 C22 H22 121.7 . . ?
C21 C22 H22 121.7 . . ?
C20 C23 H23A 109.5 . . ?
C20 C23 H23B 109.5 . . ?
C20 C23 H23C 109.5 . . ?
H23A C23 H23B 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C25 C24 C8 178.6(12) . . ?
C24 C25 H25 180.0 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
S1 N2 C11 C10 -157.1(6) . . . . ?
S1 N2 C12 C9 179.2(6) . . . . ?
S1 N2 C12 C13 -57.8(10) . . . . ?
S1 N2 C12 C16 58.8(10) . . . . ?
S1 C17 C18 C19 177.7(8) . . . . ?
S1 C17 C22 C21 -178.8(7) . . . . ?
O2 S1 N2 C11 161.0(7) . . . . ?
O2 S1 N2 C12 -29.5(8) . . . . ?
O2 S1 C17 C18 -0.2(10) . . . . ?
O2 S1 C17 C22 178.9(8) . . . . ?
O3 S1 N2 C11 30.8(8) . . . . ?
O3 S1 N2 C12 -159.6(7) . . . . ?
O3 S1 C17 C18 130.5(9) . . . . ?
O3 S1 C17 C22 -50.5(9) . . . . ?
N2 S1 C17 C18 -114.7(9) . . . . ?
N2 S1 C17 C22 64.4(9) . . . . ?
N2 C12 C13 C14 106.4(9) . . . . ?
N2 C12 C16 O1 60.0(12) . . . . ?
N2 C12 C16 C15 -120.8(9) . . . . ?
C2 C3 C4 C5 -1.2(19) . . . . ?
C2 C7 C8 C9 63.7(12) . . . . ?
C2 C7 C8 C24 -62.7(11) . . . . ?
C3 C2 C7 C6 -1.7(15) . . . . ?
C3 C2 C7 C8 -179.6(9) . . . . ?
C3 C4 C5 C6 1(2) . . . . ?
C4 C5 C6 C7 -2(2) . . . . ?
C5 C6 C7 C2 2.0(15) . . . . ?
C5 C6 C7 C8 179.9(10) . . . . ?
C6 C7 C8 C9 -114.1(9) . . . . ?
C6 C7 C8 C24 119.5(9) . . . . ?
C7 C2 C3 C4 1.3(17) . . . . ?
C7 C8 C9 C10 62.1(10) . . . . ?
C7 C8 C9 C12 -176.7(8) . . . . ?
C8 C9 C10 C11 163.8(7) . . . . ?
C8 C9 C12 N2 -140.9(7) . . . . ?
C8 C9 C12 C13 94.1(9) . . . . ?
C8 C9 C12 C16 -24.1(11) . . . . ?
C9 C10 C11 N2 -40.2(9) . . . . ?
C9 C12 C13 C14 -136.6(8) . . . . ?
C9 C12 C16 O1 -52.7(13) . . . . ?
C9 C12 C16 C15 126.5(9) . . . . ?
C10 C9 C12 N2 -15.8(9) . . . . ?
C10 C9 C12 C13 -140.8(7) . . . . ?
C10 C9 C12 C16 101.1(9) . . . . ?
C11 N2 C12 C9 -10.6(9) . . . . ?
C11 N2 C12 C13 112.4(8) . . . . ?
C11 N2 C12 C16 -130.9(8) . . . . ?
C12 N2 C11 C10 32.2(9) . . . . ?
C12 C9 C10 C11 35.2(9) . . . . ?
C12 C13 C14 C15 18.3(12) . . . . ?
C13 C12 C16 O1 -175.9(9) . . . . ?
C13 C12 C16 C15 3.3(11) . . . . ?
C13 C14 C15 C16 -15.9(13) . . . . ?
C14 C15 C16 O1 -173.1(10) . . . . ?
C14 C15 C16 C12 7.8(12) . . . . ?
C16 C12 C13 C14 -12.9(11) . . . . ?
C17 S1 N2 C11 -84.3(8) . . . . ?
C17 S1 N2 C12 85.3(8) . . . . ?
C17 C18 C19 C20 2.9(17) . . . . ?
C18 C17 C22 C21 0.2(15) . . . . ?
C18 C19 C20 C21 -3.1(17) . . . . ?
C18 C19 C20 C23 178.9(10) . . . . ?
C19 C20 C21 C22 1.9(16) . . . . ?
C20 C21 C22 C17 -0.5(15) . . . . ?
C22 C17 C18 C19 -1.3(16) . . . . ?
C23 C20 C21 C22 180.0(10) . . . . ?
C24 C8 C9 C10 -172.9(9) . . . . ?
C24 C8 C9 C12 -51.8(11) . . . . ?

_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_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.
;
_shelxl_version_number           2013-2
_database_code_depnum_ccdc_archive 'CCDC 973583'
#######################################################################
#
#                 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_sh988_2
_audit_creation_date             2013-09-13
_audit_creation_method           
;
  Olex2 1.2
  (compiled Apr 23 2013 17:54:37, GUI svn.r4466)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C13 H16 O2'
_chemical_formula_sum            'C13 H16 O2'
_chemical_formula_weight         204.26
_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'
O O 0.0106 0.0060 '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                   12.5769(11)
_cell_length_b                   7.8178(4)
_cell_length_c                   12.5456(8)
_cell_angle_alpha                90.00
_cell_angle_beta                 115.695(10)
_cell_angle_gamma                90.00
_cell_volume                     1111.56(14)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    843
_cell_measurement_temperature    293.83(10)
_cell_measurement_theta_max      23.2920
_cell_measurement_theta_min      3.8310
_exptl_absorpt_coefficient_mu    0.081
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.53484
_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_density_diffrn    1.221
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             440
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0242
_diffrn_reflns_av_unetI/netI     0.0401
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       5
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            2951
_diffrn_reflns_theta_full        25.50
_diffrn_reflns_theta_max         26.01
_diffrn_reflns_theta_min         3.17
_diffrn_ambient_temperature      293.83(10)
_diffrn_detector_area_resol_mean 16.0733
_diffrn_measured_fraction_theta_full 0.8302
_diffrn_measured_fraction_theta_max 0.7198
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -76.00  -48.40   1.2000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -19.5262  -57.0000 -120.0000 23

#__ type_ start__ end____ width___ exp.time_
  2 omega  -21.00    4.20   1.2000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -19.5262  -57.0000 -120.0000 21

#__ type_ start__ end____ width___ exp.time_
  3 omega  -50.00   65.20   1.2000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       22.8075  -19.0000   60.0000 96
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0207376000
_diffrn_orient_matrix_UB_12      0.0852908000
_diffrn_orient_matrix_UB_13      -0.0043984000
_diffrn_orient_matrix_UB_21      -0.0197019000
_diffrn_orient_matrix_UB_22      -0.0026148000
_diffrn_orient_matrix_UB_23      -0.0621973000
_diffrn_orient_matrix_UB_31      -0.0556713000
_diffrn_orient_matrix_UB_32      -0.0308284000
_diffrn_orient_matrix_UB_33      -0.0069299000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                1215
_reflns_number_total             1851
_reflns_odcompleteness_completeness 83.02
_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    
;
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         0.129
_refine_diff_density_min         -0.126
_refine_diff_density_rms         0.030
_refine_ls_extinction_coef       0.037(8)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.091
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     137
_refine_ls_number_reflns         1851
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0822
_refine_ls_R_factor_gt           0.0553
_refine_ls_restrained_S_all      1.091
_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)+(0.1000P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1645
_refine_ls_wR_factor_ref         0.1992
_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
2.a Ternary CH refined with riding coordinates:
 C6(H6)
2.b Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C3(H3A,H3B), C4(H4A,H4B), C7(H7A,H7B), C10(H10A,H10B), C11(H11A,
 H11B), C12(H12A,H12B)
2.c :
 C9(H9)
;
_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
O1 O 0.79007(19) 0.8694(3) 0.62056(17) 0.0854(8) Uani 1 1 d . . .
O2 O 0.6220(2) 1.1324(3) 0.69370(18) 0.0910(8) Uani 1 1 d . . .
C1 C 0.6186(2) 0.9821(4) 0.7131(2) 0.0646(8) Uani 1 1 d . . .
C2 C 0.5137(3) 0.8728(4) 0.6424(3) 0.0888(10) Uani 1 1 d . . .
H2A H 0.4587 0.9371 0.5748 0.107 Uiso 1 1 calc R . .
H2B H 0.4738 0.8421 0.6908 0.107 Uiso 1 1 calc R . .
C3 C 0.5502(3) 0.7110(5) 0.5997(3) 0.0961(12) Uani 1 1 d . . .
H3A H 0.4823 0.6368 0.5616 0.115 Uiso 1 1 calc R . .
H3B H 0.5791 0.7406 0.5418 0.115 Uiso 1 1 calc R . .
C4 C 0.6456(3) 0.6173(3) 0.7019(3) 0.0823(10) Uani 1 1 d . . .
H4A H 0.6691 0.5174 0.6715 0.099 Uiso 1 1 calc R . .
H4B H 0.6130 0.5775 0.7548 0.099 Uiso 1 1 calc R . .
C5 C 0.7562(2) 0.7264(3) 0.77331(19) 0.0548(7) Uani 1 1 d . . .
C6 C 0.7198(2) 0.8937(3) 0.81405(19) 0.0533(7) Uani 1 1 d . . .
H6 H 0.6904 0.8611 0.8718 0.064 Uiso 1 1 calc R . .
C7 C 0.8218(2) 1.0185(4) 0.8769(2) 0.0692(8) Uani 1 1 d . . .
H7A H 0.8927 0.9537 0.9235 0.083 Uiso 1 1 calc R . .
H7B H 0.8358 1.0822 0.8179 0.083 Uiso 1 1 calc R . .
C8 C 0.8007(2) 1.1390(4) 0.9542(2) 0.0693(8) Uani 1 1 d . . .
C9 C 0.7815(3) 1.2331(4) 1.0172(3) 0.0842(9) Uani 1 1 d . . .
H9 H 0.7663 1.3074 1.0669 0.101 Uiso 1 1 calc R . .
C10 C 0.8468(3) 0.6192(4) 0.8735(2) 0.0811(10) Uani 1 1 d . . .
H10A H 0.9018 0.6922 0.9354 0.097 Uiso 1 1 calc R . .
H10B H 0.8081 0.5444 0.9075 0.097 Uiso 1 1 calc R . .
C11 C 0.9106(3) 0.5150(4) 0.8159(3) 0.0860(10) Uani 1 1 d . . .
H11A H 0.9885 0.4806 0.8737 0.103 Uiso 1 1 calc R . .
H11B H 0.8658 0.4138 0.7773 0.103 Uiso 1 1 calc R . .
C12 C 0.9187(3) 0.6379(4) 0.7268(3) 0.0733(9) Uani 1 1 d . . .
H12A H 0.9931 0.6991 0.7608 0.088 Uiso 1 1 calc R . .
H12B H 0.9129 0.5768 0.6572 0.088 Uiso 1 1 calc R . .
C13 C 0.8185(2) 0.7586(3) 0.69530(19) 0.0554(7) 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
O1 C13 1.211(3) . ?
O2 C1 1.205(3) . ?
C1 C2 1.498(4) . ?
C1 C6 1.518(4) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C2 C3 1.521(4) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C3 C4 1.512(5) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C4 C5 1.544(4) . ?
C5 C6 1.543(3) . ?
C5 C10 1.530(3) . ?
C5 C13 1.517(3) . ?
C6 H6 0.9800 . ?
C6 C7 1.531(3) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C7 C8 1.457(4) . ?
C8 C9 1.179(4) . ?
C9 H9 0.9300 . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C10 C11 1.528(4) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C11 C12 1.510(4) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C12 C13 1.484(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
O2 C1 C2 122.4(3) . . ?
O2 C1 C6 121.5(2) . . ?
C2 C1 C6 116.1(3) . . ?
C1 C2 H2A 109.4 . . ?
C1 C2 H2B 109.4 . . ?
C1 C2 C3 111.1(2) . . ?
H2A C2 H2B 108.0 . . ?
C3 C2 H2A 109.4 . . ?
C3 C2 H2B 109.4 . . ?
C2 C3 H3A 109.5 . . ?
C2 C3 H3B 109.5 . . ?
H3A C3 H3B 108.1 . . ?
C4 C3 C2 110.7(3) . . ?
C4 C3 H3A 109.5 . . ?
C4 C3 H3B 109.5 . . ?
C3 C4 H4A 108.7 . . ?
C3 C4 H4B 108.7 . . ?
C3 C4 C5 114.1(2) . . ?
H4A C4 H4B 107.6 . . ?
C5 C4 H4A 108.7 . . ?
C5 C4 H4B 108.7 . . ?
C6 C5 C4 109.8(2) . . ?
C10 C5 C4 109.7(2) . . ?
C10 C5 C6 114.48(19) . . ?
C13 C5 C4 107.74(19) . . ?
C13 C5 C6 112.5(2) . . ?
C13 C5 C10 102.2(2) . . ?
C1 C6 C5 111.79(19) . . ?
C1 C6 H6 106.6 . . ?
C1 C6 C7 110.6(2) . . ?
C5 C6 H6 106.6 . . ?
C7 C6 C5 114.1(2) . . ?
C7 C6 H6 106.6 . . ?
C6 C7 H7A 108.8 . . ?
C6 C7 H7B 108.8 . . ?
H7A C7 H7B 107.7 . . ?
C8 C7 C6 113.7(2) . . ?
C8 C7 H7A 108.8 . . ?
C8 C7 H7B 108.8 . . ?
C9 C8 C7 178.1(3) . . ?
C8 C9 H9 180.0 . . ?
C5 C10 H10A 110.7 . . ?
C5 C10 H10B 110.7 . . ?
H10A C10 H10B 108.8 . . ?
C11 C10 C5 105.1(2) . . ?
C11 C10 H10A 110.7 . . ?
C11 C10 H10B 110.7 . . ?
C10 C11 H11A 111.1 . . ?
C10 C11 H11B 111.1 . . ?
H11A C11 H11B 109.1 . . ?
C12 C11 C10 103.2(2) . . ?
C12 C11 H11A 111.1 . . ?
C12 C11 H11B 111.1 . . ?
C11 C12 H12A 110.5 . . ?
C11 C12 H12B 110.5 . . ?
H12A C12 H12B 108.7 . . ?
C13 C12 C11 106.3(2) . . ?
C13 C12 H12A 110.5 . . ?
C13 C12 H12B 110.5 . . ?
O1 C13 C5 123.8(2) . . ?
O1 C13 C12 126.3(2) . . ?
C12 C13 C5 109.9(2) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O2 C1 C2 C3 129.8(3) . . . . ?
O2 C1 C6 C5 -131.4(3) . . . . ?
O2 C1 C6 C7 -3.0(3) . . . . ?
C1 C2 C3 C4 53.1(4) . . . . ?
C1 C6 C7 C8 75.8(3) . . . . ?
C2 C1 C6 C5 50.4(3) . . . . ?
C2 C1 C6 C7 178.8(2) . . . . ?
C2 C3 C4 C5 -56.3(4) . . . . ?
C3 C4 C5 C6 53.8(3) . . . . ?
C3 C4 C5 C10 -179.6(2) . . . . ?
C3 C4 C5 C13 -69.1(3) . . . . ?
C4 C5 C6 C1 -48.7(3) . . . . ?
C4 C5 C6 C7 -175.1(2) . . . . ?
C4 C5 C10 C11 81.7(3) . . . . ?
C4 C5 C13 O1 81.8(3) . . . . ?
C4 C5 C13 C12 -99.5(2) . . . . ?
C5 C6 C7 C8 -157.1(2) . . . . ?
C5 C10 C11 C12 36.9(3) . . . . ?
C6 C1 C2 C3 -52.1(4) . . . . ?
C6 C5 C10 C11 -154.4(2) . . . . ?
C6 C5 C13 O1 -39.4(3) . . . . ?
C6 C5 C13 C12 139.4(2) . . . . ?
C6 C7 C8 C9 27(9) . . . . ?
C10 C5 C6 C1 -172.5(2) . . . . ?
C10 C5 C6 C7 61.0(3) . . . . ?
C10 C5 C13 O1 -162.6(3) . . . . ?
C10 C5 C13 C12 16.1(3) . . . . ?
C10 C11 C12 C13 -26.5(3) . . . . ?
C11 C12 C13 O1 -174.8(3) . . . . ?
C11 C12 C13 C5 6.5(3) . . . . ?
C13 C5 C6 C1 71.3(3) . . . . ?
C13 C5 C6 C7 -55.2(3) . . . . ?
C13 C5 C10 C11 -32.4(3) . . . . ?

_database_code_depnum_ccdc_archive 'CCDC 973584'
