# Electronic Supplementary Material (ESI) for Green Chemistry.
# 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_fb4-ome

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C25 H25 N O4 S'
_chemical_formula_sum            'C25 H25 N O4 S'
_chemical_formula_weight         435.52

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'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 1 21/c 1'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   12.2796(6)
_cell_length_b                   11.7459(4)
_cell_length_c                   15.8080(9)
_cell_angle_alpha                90.00
_cell_angle_beta                 102.781(5)
_cell_angle_gamma                90.00
_cell_volume                     2223.57(18)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    1711
_cell_measurement_theta_min      3.2946
_cell_measurement_theta_max      29.1218

_exptl_crystal_description       ?
_exptl_crystal_colour            red
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.2
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.301
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             920
_exptl_absorpt_coefficient_mu    0.177
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.93855
_exptl_absorpt_correction_T_max  1.00000
_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_special_details           
;
 ?
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean 16.0938
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            9721
_diffrn_reflns_av_R_equivalents  0.0324
_diffrn_reflns_av_sigmaI/netI    0.0682
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         3.30
_diffrn_reflns_theta_max         29.19
_reflns_number_total             5074
_reflns_number_gt                2710
_reflns_threshold_expression     >2σ(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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 > 2σ(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.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0448P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         5074
_refine_ls_number_parameters     280
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1229
_refine_ls_R_factor_gt           0.0597
_refine_ls_wR_factor_ref         0.1339
_refine_ls_wR_factor_gt          0.1079
_refine_ls_goodness_of_fit_ref   1.023
_refine_ls_restrained_S_all      1.023
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

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 0.11355(7) -0.26218(5) 1.01593(5) 0.0680(3) Uani 1 1 d . . .
O3 O 0.01017(13) 0.22625(12) 0.79316(11) 0.0569(5) Uani 1 1 d . . .
O4 O 0.39745(14) 0.01584(14) 0.63752(13) 0.0699(5) Uani 1 1 d . . .
N1 N -0.01852(16) -0.14593(14) 0.89723(13) 0.0475(5) Uani 1 1 d . . .
O1 O 0.30216(16) 0.15172(16) 1.02076(12) 0.0742(6) Uani 1 1 d . . .
O2 O 0.29514(17) -0.14521(16) 1.05492(14) 0.0905(7) Uani 1 1 d . . .
C13 C 0.19867(18) 0.03753(17) 0.81983(15) 0.0419(6) Uani 1 1 d . . .
C008 C -0.0449(2) 0.13850(18) 0.79344(15) 0.0453(6) Uani 1 1 d . . .
C17 C 0.18995(19) -0.05484(18) 0.76478(16) 0.0510(6) Uani 1 1 d . . .
H17 H 0.1387 -0.1118 0.7688 0.061 Uiso 1 1 calc R . .
C14 C 0.27508(19) 0.12122(18) 0.81070(17) 0.0507(6) Uani 1 1 d . . .
H14 H 0.2830 0.1850 0.8464 0.061 Uiso 1 1 calc R . .
C9 C 0.00382(18) 0.03870(17) 0.84186(14) 0.0412(5) Uani 1 1 d . . .
C19 C -0.17492(19) -0.06888(19) 0.78878(16) 0.0515(6) Uani 1 1 d . . .
H19A H -0.2280 -0.0584 0.8254 0.062 Uiso 1 1 calc R . .
H19B H -0.1836 -0.1459 0.7662 0.062 Uiso 1 1 calc R . .
C013 C 0.32997(19) 0.0184(2) 0.69622(17) 0.0502(6) Uani 1 1 d . . .
C014 C -0.2033(2) 0.01458(19) 0.71268(17) 0.0514(6) Uani 1 1 d . . .
C6 C 0.1559(2) -0.05022(19) 0.95439(15) 0.0464(6) Uani 1 1 d . . .
C10 C -0.05951(19) -0.05567(18) 0.84306(14) 0.0421(5) Uani 1 1 d . . .
C8 C 0.12606(19) 0.04466(17) 0.88649(15) 0.0435(6) Uani 1 1 d . . .
H8 H 0.1399 0.1181 0.9163 0.052 Uiso 1 1 calc R . .
C7 C 0.0855(2) -0.14021(18) 0.95175(15) 0.0473(6) Uani 1 1 d . . .
C15 C 0.3396(2) 0.1119(2) 0.74957(18) 0.0572(7) Uani 1 1 d . . .
H15 H 0.3900 0.1693 0.7446 0.069 Uiso 1 1 calc R . .
C020 C -0.1445(2) -0.0215(2) 0.64112(17) 0.0646(7) Uani 1 1 d . . .
H02A H -0.0651 -0.0206 0.6634 0.097 Uiso 1 1 calc R . .
H02B H -0.1636 0.0305 0.5933 0.097 Uiso 1 1 calc R . .
H02C H -0.1678 -0.0969 0.6219 0.097 Uiso 1 1 calc R . .
C20 C -0.16535(19) 0.13272(18) 0.74632(17) 0.0559(7) Uani 1 1 d . . .
H20A H -0.1771 0.1851 0.6977 0.067 Uiso 1 1 calc R . .
H20B H -0.2116 0.1578 0.7852 0.067 Uiso 1 1 calc R . .
C11 C -0.0781(2) -0.25478(18) 0.89717(17) 0.0598(7) Uani 1 1 d . . .
H11A H -0.0666 -0.3030 0.8501 0.072 Uiso 1 1 calc R . .
H11B H -0.1575 -0.2419 0.8905 0.072 Uiso 1 1 calc R . .
C16 C 0.2544(2) -0.06594(19) 0.70393(17) 0.0531(6) Uani 1 1 d . . .
H16 H 0.2470 -0.1298 0.6684 0.064 Uiso 1 1 calc R . .
C5 C 0.2619(2) -0.0552(2) 1.01616(17) 0.0602(7) Uani 1 1 d . . .
C12 C -0.0293(2) -0.3095(2) 0.98389(19) 0.0715(8) Uani 1 1 d . . .
H12A H -0.0324 -0.3918 0.9788 0.086 Uiso 1 1 calc R . .
H12B H -0.0709 -0.2864 1.0265 0.086 Uiso 1 1 calc R . .
C4 C 0.3379(2) 0.0424(2) 1.03969(17) 0.0627(7) Uani 1 1 d . . .
C18 C 0.3964(2) -0.0843(3) 0.5872(2) 0.0894(10) Uani 1 1 d . . .
H18A H 0.4477 -0.0758 0.5498 0.134 Uiso 1 1 calc R . .
H18B H 0.3225 -0.0967 0.5529 0.134 Uiso 1 1 calc R . .
H18C H 0.4183 -0.1482 0.6250 0.134 Uiso 1 1 calc R . .
C028 C -0.3296(2) 0.0142(2) 0.6771(2) 0.0823(9) Uani 1 1 d . . .
H02D H -0.3481 0.0660 0.6291 0.123 Uiso 1 1 calc R . .
H02E H -0.3664 0.0375 0.7218 0.123 Uiso 1 1 calc R . .
H02F H -0.3535 -0.0612 0.6580 0.123 Uiso 1 1 calc R . .
C3 C 0.4438(3) 0.0445(4) 1.0846(2) 0.0983(11) Uani 1 1 d . . .
H3 H 0.4872 -0.0185 1.1057 0.118 Uiso 1 1 calc R . .
C1 C 0.3908(3) 0.2199(3) 1.0551(2) 0.0945(11) Uani 1 1 d . . .
H1 H 0.3902 0.2989 1.0515 0.113 Uiso 1 1 calc R . .
C2 C 0.4780(3) 0.1584(4) 1.0942(3) 0.1170(14) Uani 1 1 d . . .
H2 H 0.5478 0.1854 1.1223 0.140 Uiso 1 1 calc R . .


_geom_special_details            
;
 All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell s.u.'s are taken
 into account individually in the estimation of s.u.'s in distances, angles
 and torsion angles; correlations between s.u.'s in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell s.u.'s is used for estimating s.u.'s 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 C7 1.745(2) . ?
S1 C12 1.803(3) . ?
O3 C008 1.233(2) . ?
O4 C013 1.374(3) . ?
O4 C18 1.418(3) . ?
N1 C7 1.375(3) . ?
N1 C10 1.386(3) . ?
N1 C11 1.473(3) . ?
O1 C1 1.364(3) . ?
O1 C4 1.369(3) . ?
O2 C5 1.245(3) . ?
C13 C17 1.380(3) . ?
C13 C14 1.388(3) . ?
C13 C8 1.526(3) . ?
C008 C9 1.454(3) . ?
C008 C20 1.503(3) . ?
C17 C16 1.380(3) . ?
C14 C15 1.383(3) . ?
C9 C10 1.357(3) . ?
C9 C8 1.512(3) . ?
C19 C10 1.494(3) . ?
C19 C014 1.531(3) . ?
C013 C15 1.373(3) . ?
C013 C16 1.381(3) . ?
C014 C20 1.522(3) . ?
C014 C028 1.528(3) . ?
C014 C020 1.531(3) . ?
C6 C7 1.361(3) . ?
C6 C5 1.445(3) . ?
C6 C8 1.534(3) . ?
C11 C12 1.512(3) . ?
C5 C4 1.473(4) . ?
C4 C3 1.337(4) . ?
C3 C2 1.400(4) . ?
C1 C2 1.325(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
C7 S1 C12 92.00(12) . . ?
C013 O4 C18 117.69(19) . . ?
C7 N1 C10 120.66(18) . . ?
C7 N1 C11 115.78(18) . . ?
C10 N1 C11 123.5(2) . . ?
C1 O1 C4 105.9(3) . . ?
C17 C13 C14 116.8(2) . . ?
C17 C13 C8 120.20(19) . . ?
C14 C13 C8 123.0(2) . . ?
O3 C008 C9 120.9(2) . . ?
O3 C008 C20 121.1(2) . . ?
C9 C008 C20 118.0(2) . . ?
C13 C17 C16 122.5(2) . . ?
C15 C14 C13 121.4(2) . . ?
C10 C9 C008 119.7(2) . . ?
C10 C9 C8 122.97(19) . . ?
C008 C9 C8 117.30(18) . . ?
C10 C19 C014 114.02(18) . . ?
C15 C013 O4 116.7(2) . . ?
C15 C013 C16 119.2(2) . . ?
O4 C013 C16 124.1(2) . . ?
C20 C014 C028 109.81(19) . . ?
C20 C014 C020 110.6(2) . . ?
C028 C014 C020 109.5(2) . . ?
C20 C014 C19 108.1(2) . . ?
C028 C014 C19 108.9(2) . . ?
C020 C014 C19 109.93(19) . . ?
C7 C6 C5 117.4(2) . . ?
C7 C6 C8 119.4(2) . . ?
C5 C6 C8 122.8(2) . . ?
C9 C10 N1 120.2(2) . . ?
C9 C10 C19 123.4(2) . . ?
N1 C10 C19 116.39(19) . . ?
C9 C8 C13 110.28(18) . . ?
C9 C8 C6 110.59(18) . . ?
C13 C8 C6 110.94(17) . . ?
C6 C7 N1 123.6(2) . . ?
C6 C7 S1 125.3(2) . . ?
N1 C7 S1 111.15(17) . . ?
C013 C15 C14 120.5(2) . . ?
C008 C20 C014 113.96(18) . . ?
N1 C11 C12 105.7(2) . . ?
C17 C16 C013 119.6(2) . . ?
O2 C5 C6 121.0(2) . . ?
O2 C5 C4 114.6(2) . . ?
C6 C5 C4 124.4(2) . . ?
C11 C12 S1 106.81(17) . . ?
C3 C4 O1 109.0(3) . . ?
C3 C4 C5 129.5(3) . . ?
O1 C4 C5 121.3(2) . . ?
C4 C3 C2 108.0(3) . . ?
C2 C1 O1 110.9(3) . . ?
C1 C2 C3 106.2(3) . . ?

_diffrn_measured_fraction_theta_max 0.844
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.174
_refine_diff_density_min         -0.242
_refine_diff_density_rms         0.040
_database_code_depnum_ccdc_archive 'CCDC 960941'
#######################################################################
#
#                 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_1-ac-ta-d-a1

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C31 H29 N O2 S'
_chemical_formula_sum            'C31 H29 N O2 S'
_chemical_formula_weight         479.61

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'

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'P n a 21'
_symmetry_space_group_name_Hall  'P 2c -2n'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, z+1/2'
'-x+1/2, y+1/2, z+1/2'
'x+1/2, -y+1/2, z'

_cell_length_a                   16.581(5)
_cell_length_b                   11.236(5)
_cell_length_c                   14.597(5)
_cell_angle_alpha                90.000(5)
_cell_angle_beta                 90.000(5)
_cell_angle_gamma                90.000(5)
_cell_volume                     2719.5(17)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.171
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1016
_exptl_absorpt_coefficient_mu    0.146
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.92523
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.34.49 (release 20-01-2011 CrysAlis171 .NET)
(compiled Jan 20 2011,15:58:25)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            8767
_diffrn_reflns_av_R_equivalents  0.0230
_diffrn_reflns_av_sigmaI/netI    0.0332
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         3.36
_diffrn_reflns_theta_max         29.06
_reflns_number_total             4252
_reflns_number_gt                3176
_reflns_threshold_expression     >2σ(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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 > 2σ(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.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.2000P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.5(2)
_refine_ls_number_reflns         4252
_refine_ls_number_parameters     316
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.1184
_refine_ls_R_factor_gt           0.0975
_refine_ls_wR_factor_ref         0.3089
_refine_ls_wR_factor_gt          0.2822
_refine_ls_goodness_of_fit_ref   1.199
_refine_ls_restrained_S_all      1.199
_refine_ls_shift/su_max          0.023
_refine_ls_shift/su_mean         0.005

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 0.06562(11) 0.34933(15) 0.12770(16) 0.0732(6) Uani 1 1 d . . .
O2 O -0.0338(3) -0.1445(4) 0.3567(4) 0.0666(13) Uani 1 1 d . . .
O1 O 0.1933(3) 0.2134(4) 0.1324(5) 0.0783(16) Uani 1 1 d . . .
C14 C 0.0419(3) 0.0036(5) 0.2276(4) 0.0429(12) Uani 1 1 d . . .
H14 H 0.0770 -0.0296 0.2752 0.052 Uiso 1 1 calc R . .
C15 C -0.0400(3) 0.0321(5) 0.2706(3) 0.0420(11) Uani 1 1 d . . .
C12 C 0.0797(3) 0.1221(5) 0.1934(4) 0.0434(12) Uani 1 1 d . . .
N1 N -0.0487(3) 0.2205(5) 0.1989(4) 0.0606(14) Uani 1 1 d . . .
C5 C 0.3017(4) -0.0813(5) 0.3107(5) 0.0546(15) Uani 1 1 d . . .
C16 C -0.0826(3) 0.1321(6) 0.2498(4) 0.0500(13) Uani 1 1 d . . .
C10 C 0.2438(4) 0.0064(5) 0.2894(5) 0.0512(13) Uani 1 1 d . . .
C20 C -0.1536(4) -0.0254(6) 0.3791(5) 0.0613(16) Uani 1 1 d . . .
H20A H -0.1784 -0.0999 0.3972 0.074 Uiso 1 1 calc R . .
H20B H -0.1455 0.0214 0.4342 0.074 Uiso 1 1 calc R . .
C25 C 0.0341(3) -0.0869(4) 0.1516(4) 0.0477(13) Uani 1 1 d . . .
C19 C -0.0724(3) -0.0519(5) 0.3375(4) 0.0479(13) Uani 1 1 d . . .
C22 C -0.2106(4) 0.0400(5) 0.3175(5) 0.0556(14) Uani 1 1 d . . .
C24 C -0.2851(5) 0.0766(8) 0.3686(6) 0.080(2) Uani 1 1 d . . .
H24A H -0.3206 0.1188 0.3281 0.120 Uiso 1 1 calc R . .
H24B H -0.2704 0.1274 0.4188 0.120 Uiso 1 1 calc R . .
H24C H -0.3119 0.0071 0.3917 0.120 Uiso 1 1 calc R . .
C2 C 0.2566(4) -0.0401(6) 0.1312(5) 0.0625(15) Uani 1 1 d . . .
H2 H 0.2407 -0.0279 0.0708 0.075 Uiso 1 1 calc R . .
C1 C 0.2217(3) 0.0256(5) 0.1959(4) 0.0492(13) Uani 1 1 d . . .
C13 C 0.0326(3) 0.2170(5) 0.1774(4) 0.0506(14) Uani 1 1 d . . .
C11 C 0.1641(4) 0.1295(5) 0.1716(4) 0.0491(13) Uani 1 1 d . . .
C9 C 0.2097(4) 0.0724(6) 0.3636(5) 0.0598(16) Uani 1 1 d . . .
H9 H 0.1709 0.1300 0.3513 0.072 Uiso 1 1 calc R . .
C26 C 0.0729(4) -0.1971(6) 0.1568(5) 0.0637(17) Uani 1 1 d . . .
H26 H 0.1053 -0.2136 0.2072 0.076 Uiso 1 1 calc R . .
C21 C -0.1677(4) 0.1540(5) 0.2843(5) 0.0556(15) Uani 1 1 d . . .
H21A H -0.1992 0.1895 0.2355 0.067 Uiso 1 1 calc R . .
H21B H -0.1656 0.2106 0.3345 0.067 Uiso 1 1 calc R . .
C29 C -0.0172(5) -0.1444(7) 0.0036(5) 0.0695(19) Uani 1 1 d . . .
H29 H -0.0470 -0.1251 -0.0483 0.083 Uiso 1 1 calc R . .
C30 C -0.0091(5) -0.0648(7) 0.0721(5) 0.0700(18) Uani 1 1 d . . .
H30 H -0.0339 0.0090 0.0657 0.084 Uiso 1 1 calc R . .
C4 C 0.3366(5) -0.1459(6) 0.2361(7) 0.074(2) Uani 1 1 d . . .
H4 H 0.3752 -0.2038 0.2484 0.088 Uiso 1 1 calc R . .
C27 C 0.0645(5) -0.2810(7) 0.0901(7) 0.077(2) Uani 1 1 d . . .
H27 H 0.0890 -0.3548 0.0975 0.092 Uiso 1 1 calc R . .
C28 C 0.0202(5) -0.2584(7) 0.0111(5) 0.0690(19) Uani 1 1 d . . .
C6 C 0.3226(6) -0.1028(8) 0.4028(7) 0.085(2) Uani 1 1 d . . .
H6 H 0.3614 -0.1600 0.4162 0.102 Uiso 1 1 calc R . .
C3 C 0.3148(5) -0.1253(6) 0.1479(6) 0.0703(19) Uani 1 1 d . . .
H3 H 0.3385 -0.1673 0.1001 0.084 Uiso 1 1 calc R . .
C18 C -0.0878(5) 0.3354(6) 0.1785(7) 0.076(2) Uani 1 1 d . . .
H18A H -0.1300 0.3235 0.1334 0.091 Uiso 1 1 calc R . .
H18B H -0.1125 0.3666 0.2337 0.091 Uiso 1 1 calc R . .
C8 C 0.2328(6) 0.0529(8) 0.4517(6) 0.083(2) Uani 1 1 d . . .
H8 H 0.2131 0.1010 0.4985 0.100 Uiso 1 1 calc R . .
C23 C -0.2337(6) -0.0363(8) 0.2343(7) 0.083(2) Uani 1 1 d . . .
H23A H -0.1857 -0.0601 0.2023 0.124 Uiso 1 1 calc R . .
H23B H -0.2675 0.0091 0.1940 0.124 Uiso 1 1 calc R . .
H23C H -0.2623 -0.1058 0.2547 0.124 Uiso 1 1 calc R . .
C31 C 0.0088(9) -0.3475(8) -0.0640(7) 0.103(3) Uani 1 1 d . . .
H31A H -0.0250 -0.3141 -0.1108 0.155 Uiso 1 1 calc R . .
H31B H -0.0162 -0.4178 -0.0397 0.155 Uiso 1 1 calc R . .
H31C H 0.0603 -0.3678 -0.0898 0.155 Uiso 1 1 calc R . .
C7 C 0.2874(6) -0.0419(10) 0.4721(7) 0.097(3) Uani 1 1 d . . .
H7 H 0.2987 -0.0617 0.5326 0.116 Uiso 1 1 calc R . .
C17 C -0.0323(7) 0.4165(10) 0.1454(15) 0.180(9) Uani 1 1 d . . .
H17A H -0.0272 0.4818 0.1885 0.216 Uiso 1 1 calc R . .
H17B H -0.0517 0.4488 0.0878 0.216 Uiso 1 1 calc R . .


_geom_special_details            
;
 All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell s.u.'s are taken
 into account individually in the estimation of s.u.'s in distances, angles
 and torsion angles; correlations between s.u.'s in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell s.u.'s is used for estimating s.u.'s 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 C13 1.742(5) . ?
S1 C17 1.810(9) . ?
O2 C19 1.253(7) . ?
O1 C11 1.205(7) . ?
C14 C25 1.511(8) . ?
C14 C15 1.531(7) . ?
C14 C12 1.553(7) . ?
C15 C16 1.362(8) . ?
C15 C19 1.461(7) . ?
C12 C13 1.341(8) . ?
C12 C11 1.438(8) . ?
N1 C16 1.361(8) . ?
N1 C13 1.386(8) . ?
N1 C18 1.475(8) . ?
C5 C6 1.408(11) . ?
C5 C10 1.411(8) . ?
C5 C4 1.431(11) . ?
C16 C21 1.517(8) . ?
C10 C1 1.429(9) . ?
C10 C9 1.430(10) . ?
C20 C22 1.498(9) . ?
C20 C19 1.506(9) . ?
C25 C30 1.386(9) . ?
C25 C26 1.397(9) . ?
C22 C24 1.501(10) . ?
C22 C23 1.535(12) . ?
C22 C21 1.543(8) . ?
C2 C1 1.331(9) . ?
C2 C3 1.382(10) . ?
C1 C11 1.550(8) . ?
C9 C8 1.360(10) . ?
C26 C27 1.363(10) . ?
C29 C30 1.349(11) . ?
C29 C28 1.428(11) . ?
C4 C3 1.356(14) . ?
C27 C28 1.390(12) . ?
C28 C31 1.496(11) . ?
C6 C7 1.353(13) . ?
C18 C17 1.382(12) . ?
C8 C7 1.430(12) . ?

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
C13 S1 C17 90.9(3) . . ?
C25 C14 C15 111.4(4) . . ?
C25 C14 C12 112.0(4) . . ?
C15 C14 C12 108.1(4) . . ?
C16 C15 C19 119.5(5) . . ?
C16 C15 C14 122.8(5) . . ?
C19 C15 C14 117.7(4) . . ?
C13 C12 C11 118.8(5) . . ?
C13 C12 C14 120.2(5) . . ?
C11 C12 C14 120.8(4) . . ?
C16 N1 C13 120.3(5) . . ?
C16 N1 C18 124.6(5) . . ?
C13 N1 C18 114.0(5) . . ?
C6 C5 C10 119.9(7) . . ?
C6 C5 C4 122.7(7) . . ?
C10 C5 C4 117.4(7) . . ?
C15 C16 N1 120.6(5) . . ?
C15 C16 C21 122.8(5) . . ?
N1 C16 C21 116.5(5) . . ?
C5 C10 C1 119.4(6) . . ?
C5 C10 C9 117.7(6) . . ?
C1 C10 C9 122.9(5) . . ?
C22 C20 C19 114.8(5) . . ?
C30 C25 C26 116.2(6) . . ?
C30 C25 C14 122.6(5) . . ?
C26 C25 C14 121.1(6) . . ?
O2 C19 C15 119.9(5) . . ?
O2 C19 C20 122.1(5) . . ?
C15 C19 C20 118.0(5) . . ?
C20 C22 C24 110.8(6) . . ?
C20 C22 C23 111.0(6) . . ?
C24 C22 C23 109.9(7) . . ?
C20 C22 C21 107.7(5) . . ?
C24 C22 C21 108.0(6) . . ?
C23 C22 C21 109.3(6) . . ?
C1 C2 C3 124.2(7) . . ?
C2 C1 C10 118.9(6) . . ?
C2 C1 C11 121.5(6) . . ?
C10 C1 C11 119.4(5) . . ?
C12 C13 N1 123.3(5) . . ?
C12 C13 S1 124.6(4) . . ?
N1 C13 S1 112.1(4) . . ?
O1 C11 C12 122.8(5) . . ?
O1 C11 C1 116.7(5) . . ?
C12 C11 C1 120.4(5) . . ?
C8 C9 C10 121.5(6) . . ?
C27 C26 C25 121.8(7) . . ?
C16 C21 C22 113.5(5) . . ?
C30 C29 C28 119.7(7) . . ?
C29 C30 C25 123.6(7) . . ?
C3 C4 C5 121.9(6) . . ?
C26 C27 C28 121.4(7) . . ?
C27 C28 C29 117.2(7) . . ?
C27 C28 C31 123.5(8) . . ?
C29 C28 C31 119.3(8) . . ?
C7 C6 C5 121.4(7) . . ?
C4 C3 C2 118.2(7) . . ?
C17 C18 N1 110.9(6) . . ?
C9 C8 C7 119.6(8) . . ?
C6 C7 C8 119.7(8) . . ?
C18 C17 S1 111.8(6) . . ?

_diffrn_measured_fraction_theta_max 0.870
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         1.243
_refine_diff_density_min         -0.325
_refine_diff_density_rms         0.097
_database_code_depnum_ccdc_archive 'CCDC 1012571'
#######################################################################
#
#                 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_al-3

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C22 H25 N O2 S'
_chemical_formula_sum            'C22 H25 N O2 S'
_chemical_formula_weight         367.49

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'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 1 21/n 1'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   6.4263(3)
_cell_length_b                   12.9536(5)
_cell_length_c                   23.9037(11)
_cell_angle_alpha                90.00
_cell_angle_beta                 97.062(5)
_cell_angle_gamma                90.00
_cell_volume                     1974.74(15)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    1925
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.2
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.236
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             784
_exptl_absorpt_coefficient_mu    0.179
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.938
_exptl_absorpt_correction_T_max  0.965
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.34.49 (release 20-01-2011 CrysAlis171 .NET)
(compiled Jan 20 2011,15:58:25)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            8184
_diffrn_reflns_av_R_equivalents  0.0214
_diffrn_reflns_av_sigmaI/netI    0.0420
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         3.02
_diffrn_reflns_theta_max         29.05
_reflns_number_total             5272
_reflns_number_gt                2916
_reflns_threshold_expression     >2σ(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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 > 2σ(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.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0652P)²+0.6362P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         5272
_refine_ls_number_parameters     235
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0950
_refine_ls_R_factor_gt           0.0586
_refine_ls_wR_factor_ref         0.1621
_refine_ls_wR_factor_gt          0.1367
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_restrained_S_all      1.025
_refine_ls_shift/su_max          0.006
_refine_ls_shift/su_mean         0.001

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
S S 0.29099(11) 0.30246(5) 0.24699(3) 0.0617(2) Uani 1 1 d . . .
N1 N 0.4584(3) 0.15358(14) 0.31011(7) 0.0436(4) Uani 1 1 d . . .
C12 C 0.7884(3) 0.14766(16) 0.36666(9) 0.0409(5) Uani 1 1 d . . .
C13 C 0.6193(3) 0.09818(16) 0.34077(8) 0.0393(5) Uani 1 1 d . . .
C14 C 0.4889(3) 0.25628(17) 0.29772(8) 0.0426(5) Uani 1 1 d . . .
C4 C 0.8010(3) 0.26412(16) 0.37032(9) 0.0419(5) Uani 1 1 d . . .
H4 H 0.9447 0.2848 0.3658 0.050 Uiso 1 1 calc R . .
C5 C 0.7532(4) 0.30128(16) 0.42800(9) 0.0425(5) Uani 1 1 d . . .
C16 C 0.2811(4) 0.1040(2) 0.27598(10) 0.0533(6) Uani 1 1 d . . .
H16A H 0.2095 0.0577 0.2991 0.064 Uiso 1 1 calc R . .
H16B H 0.3302 0.0643 0.2458 0.064 Uiso 1 1 calc R . .
C3 C 0.6546(4) 0.31126(17) 0.32224(9) 0.0436(5) Uani 1 1 d . . .
O1 O 0.5620(3) 0.45604(14) 0.26587(9) 0.0835(7) Uani 1 1 d . . .
O2 O 1.1318(3) 0.13201(14) 0.41158(9) 0.0697(5) Uani 1 1 d . . .
C8AA C 0.9698(4) 0.08905(18) 0.39193(10) 0.0489(6) Uani 1 1 d . . .
C2 C 0.6830(4) 0.41708(19) 0.30408(11) 0.0542(6) Uani 1 1 d . . .
C17 C 0.5938(4) -0.01663(17) 0.34197(10) 0.0507(6) Uani 1 1 d . . .
H17A H 0.6235 -0.0448 0.3062 0.061 Uiso 1 1 calc R . .
H17B H 0.4490 -0.0326 0.3461 0.061 Uiso 1 1 calc R . .
C19 C 0.9573(4) -0.02708(19) 0.38982(12) 0.0600(7) Uani 1 1 d . . .
H19A H 1.0455 -0.0550 0.4221 0.072 Uiso 1 1 calc R . .
H19B H 1.0129 -0.0509 0.3562 0.072 Uiso 1 1 calc R . .
C10 C 0.9075(4) 0.3470(2) 0.46513(11) 0.0636(7) Uani 1 1 d . . .
H10 H 1.0422 0.3537 0.4552 0.076 Uiso 1 1 calc R . .
C15 C 0.1355(4) 0.1870(2) 0.25215(12) 0.0679(8) Uani 1 1 d . . .
H15A H 0.0281 0.1992 0.2766 0.081 Uiso 1 1 calc R . .
H15B H 0.0678 0.1672 0.2152 0.081 Uiso 1 1 calc R . .
C8 C 0.6670(5) 0.3751(2) 0.53345(11) 0.0618(7) Uani 1 1 d . . .
C18 C 0.7364(4) -0.06948(18) 0.38965(10) 0.0535(6) Uani 1 1 d . . .
C7 C 0.5159(4) 0.3256(2) 0.49682(11) 0.0679(8) Uani 1 1 d . . .
H7 H 0.3826 0.3163 0.5073 0.082 Uiso 1 1 calc R . .
C6 C 0.5583(4) 0.2897(2) 0.44513(11) 0.0597(7) Uani 1 1 d . . .
H6 H 0.4529 0.2570 0.4214 0.072 Uiso 1 1 calc R . .
C1 C 0.8621(5) 0.4791(2) 0.33168(13) 0.0697(8) Uani 1 1 d . . .
H1A H 0.8593 0.5466 0.3150 0.104 Uiso 1 1 calc R . .
H1B H 0.9915 0.4454 0.3266 0.104 Uiso 1 1 calc R . .
H1C H 0.8508 0.4852 0.3712 0.104 Uiso 1 1 calc R . .
C9 C 0.8646(5) 0.3829(2) 0.51683(12) 0.0730(8) Uani 1 1 d . . .
H9 H 0.9717 0.4131 0.5411 0.088 Uiso 1 1 calc R . .
C21 C 0.7363(6) -0.1858(2) 0.37810(15) 0.0817(9) Uani 1 1 d . . .
H21A H 0.8243 -0.2200 0.4078 0.123 Uiso 1 1 calc R . .
H21B H 0.7887 -0.1984 0.3428 0.123 Uiso 1 1 calc R . .
H21C H 0.5959 -0.2119 0.3764 0.123 Uiso 1 1 calc R . .
C20 C 0.6558(5) -0.0489(2) 0.44621(12) 0.0773(9) Uani 1 1 d . . .
H20A H 0.7452 -0.0828 0.4757 0.116 Uiso 1 1 calc R . .
H20B H 0.5156 -0.0751 0.4451 0.116 Uiso 1 1 calc R . .
H20C H 0.6560 0.0240 0.4533 0.116 Uiso 1 1 calc R . .
C11 C 0.6179(6) 0.4182(3) 0.58931(13) 0.0991(12) Uani 1 1 d . . .
H11A H 0.7414 0.4497 0.6087 0.149 Uiso 1 1 calc R . .
H11B H 0.5725 0.3633 0.6119 0.149 Uiso 1 1 calc R . .
H11C H 0.5087 0.4689 0.5827 0.149 Uiso 1 1 calc R . .


_geom_special_details            
;
 All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell s.u.'s are taken
 into account individually in the estimation of s.u.'s in distances, angles
 and torsion angles; correlations between s.u.'s in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell s.u.'s is used for estimating s.u.'s 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
S C14 1.751(2) . ?
S C15 1.811(3) . ?
N1 C14 1.382(3) . ?
N1 C13 1.391(3) . ?
N1 C16 1.466(3) . ?
C12 C13 1.345(3) . ?
C12 C8AA 1.458(3) . ?
C12 C4 1.513(3) . ?
C13 C17 1.497(3) . ?
C14 C3 1.354(3) . ?
C4 C3 1.521(3) . ?
C4 C5 1.527(3) . ?
C5 C6 1.373(3) . ?
C5 C10 1.380(3) . ?
C16 C15 1.492(4) . ?
C3 C2 1.456(3) . ?
O1 C2 1.232(3) . ?
O2 C8AA 1.222(3) . ?
C8AA C19 1.507(3) . ?
C2 C1 1.489(4) . ?
C17 C18 1.533(3) . ?
C19 C18 1.521(4) . ?
C10 C9 1.379(4) . ?
C8 C9 1.381(4) . ?
C8 C7 1.382(4) . ?
C8 C11 1.516(4) . ?
C18 C20 1.530(4) . ?
C18 C21 1.531(3) . ?
C7 C6 1.378(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
C14 S C15 91.75(11) . . ?
C14 N1 C13 119.59(17) . . ?
C14 N1 C16 115.05(18) . . ?
C13 N1 C16 122.95(18) . . ?
C13 C12 C8AA 120.1(2) . . ?
C13 C12 C4 122.41(19) . . ?
C8AA C12 C4 117.45(19) . . ?
C12 C13 N1 120.19(19) . . ?
C12 C13 C17 123.3(2) . . ?
N1 C13 C17 116.52(18) . . ?
C3 C14 N1 122.57(19) . . ?
C3 C14 S 125.88(17) . . ?
N1 C14 S 111.54(15) . . ?
C12 C4 C3 109.46(17) . . ?
C12 C4 C5 110.57(17) . . ?
C3 C4 C5 112.43(18) . . ?
C6 C5 C10 117.7(2) . . ?
C6 C5 C4 121.79(19) . . ?
C10 C5 C4 120.5(2) . . ?
N1 C16 C15 107.7(2) . . ?
C14 C3 C2 119.1(2) . . ?
C14 C3 C4 119.78(19) . . ?
C2 C3 C4 121.0(2) . . ?
O2 C8AA C12 121.5(2) . . ?
O2 C8AA C19 120.4(2) . . ?
C12 C8AA C19 118.0(2) . . ?
O1 C2 C3 121.1(2) . . ?
O1 C2 C1 119.4(2) . . ?
C3 C2 C1 119.6(2) . . ?
C13 C17 C18 113.63(19) . . ?
C8AA C19 C18 114.0(2) . . ?
C9 C10 C5 120.9(3) . . ?
C16 C15 S 107.22(18) . . ?
C9 C8 C7 116.8(2) . . ?
C9 C8 C11 121.7(3) . . ?
C7 C8 C11 121.5(3) . . ?
C19 C18 C20 110.6(2) . . ?
C19 C18 C21 109.6(2) . . ?
C20 C18 C21 109.7(2) . . ?
C19 C18 C17 108.3(2) . . ?
C20 C18 C17 110.0(2) . . ?
C21 C18 C17 108.6(2) . . ?
C6 C7 C8 121.6(3) . . ?
C5 C6 C7 121.2(2) . . ?
C10 C9 C8 121.7(2) . . ?

_diffrn_measured_fraction_theta_max 0.852
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.364
_refine_diff_density_min         -0.269
_refine_diff_density_rms         0.044
_database_code_depnum_ccdc_archive 'CCDC 1012297'
