# 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_ltp257
#TrackingRef '16428_web_deposit_cif_file_0_KohPengFeiJackson_1356499898.7.cif'


_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_absolute_configuration ad
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C18 H17 N O3 S'
_chemical_formula_sum            'C18 H17 N O3 S'
_chemical_formula_weight         327.39

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   P2(1)

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

_cell_length_a                   9.9921(7)
_cell_length_b                   8.0950(6)
_cell_length_c                   10.5243(9)
_cell_angle_alpha                90.00
_cell_angle_beta                 107.490(2)
_cell_angle_gamma                90.00
_cell_volume                     811.91(11)
_cell_formula_units_Z            2
_cell_measurement_temperature    103(2)
_cell_measurement_reflns_used    4305
_cell_measurement_theta_min      3.24
_cell_measurement_theta_max      28.38

_exptl_crystal_description       block
_exptl_crystal_colour            orange
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.24
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.339
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             344
_exptl_absorpt_coefficient_mu    0.213
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9195
_exptl_absorpt_correction_T_max  0.9505
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      103(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  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            3983
_diffrn_reflns_av_R_equivalents  0.0000
_diffrn_reflns_av_sigmaI/netI    0.0396
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.14
_diffrn_reflns_theta_max         28.57
_reflns_number_total             3983
_reflns_number_gt                3785
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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.
;

_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)+(0.0423P)²+0.1799P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_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   -0.05(6)
_refine_ls_number_reflns         3983
_refine_ls_number_parameters     209
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0369
_refine_ls_R_factor_gt           0.0342
_refine_ls_wR_factor_ref         0.0855
_refine_ls_wR_factor_gt          0.0824
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_restrained_S_all      1.063
_refine_ls_shift/su_max          0.000
_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
C1 C 0.62158(18) 0.5251(2) 0.59456(16) 0.0156(3) Uani 1 1 d . . .
C2 C 0.72819(17) 0.6669(2) 0.61692(15) 0.0132(3) Uani 1 1 d . . .
H2 H 0.6737 0.7722 0.6076 0.016 Uiso 1 1 calc R . .
C3 C 0.88274(19) 0.5058(2) 0.81640(17) 0.0167(3) Uani 1 1 d . . .
H3A H 0.9018 0.5155 0.9140 0.020 Uiso 1 1 calc R . .
H3B H 0.9731 0.4830 0.7992 0.020 Uiso 1 1 calc R . .
C4 C 0.78690(19) 0.3634(2) 0.76789(18) 0.0196(4) Uani 1 1 d . . .
H4 H 0.8131 0.2595 0.8101 0.024 Uiso 1 1 calc R . .
C5 C 0.6667(2) 0.3719(2) 0.66915(18) 0.0210(4) Uani 1 1 d . . .
H5 H 0.6090 0.2765 0.6467 0.025 Uiso 1 1 calc R . .
C6 C 0.79875(17) 0.6665(2) 0.50733(15) 0.0142(3) Uani 1 1 d . . .
C7 C 0.74729(19) 0.7739(2) 0.39998(17) 0.0180(4) Uani 1 1 d . . .
H7 H 0.6738 0.8486 0.3995 0.022 Uiso 1 1 calc R . .
C8 C 0.8030(2) 0.7722(2) 0.29367(18) 0.0215(4) Uani 1 1 d . . .
H8 H 0.7665 0.8445 0.2204 0.026 Uiso 1 1 calc R . .
C9 C 0.91182(19) 0.6652(2) 0.29416(17) 0.0209(4) Uani 1 1 d . . .
H9 H 0.9497 0.6641 0.2215 0.025 Uiso 1 1 calc R . .
C10 C 0.9648(2) 0.5599(2) 0.40177(18) 0.0229(4) Uani 1 1 d . . .
H10 H 1.0403 0.4878 0.4032 0.027 Uiso 1 1 calc R . .
C11 C 0.9083(2) 0.5592(2) 0.50742(18) 0.0204(4) Uani 1 1 d . . .
H11 H 0.9444 0.4856 0.5799 0.024 Uiso 1 1 calc R . .
C12 C 0.63073(17) 0.7919(2) 0.85981(15) 0.0148(3) Uani 1 1 d . . .
C13 C 0.52315(19) 0.8817(2) 0.77274(17) 0.0185(3) Uani 1 1 d . . .
H13 H 0.5431 0.9575 0.7120 0.022 Uiso 1 1 calc R . .
C14 C 0.38597(19) 0.8594(2) 0.77532(17) 0.0207(4) Uani 1 1 d . . .
H14 H 0.3121 0.9203 0.7158 0.025 Uiso 1 1 calc R . .
C15 C 0.3558(2) 0.7484(2) 0.86466(18) 0.0214(4) Uani 1 1 d . . .
C16 C 0.2067(2) 0.7273(3) 0.8681(2) 0.0320(5) Uani 1 1 d . . .
H16A H 0.2026 0.6367 0.9285 0.048 Uiso 1 1 calc R . .
H16B H 0.1457 0.7019 0.7783 0.048 Uiso 1 1 calc R . .
H16C H 0.1751 0.8298 0.8996 0.048 Uiso 1 1 calc R . .
C17 C 0.4656(2) 0.6597(3) 0.95097(19) 0.0261(4) Uani 1 1 d . . .
H17 H 0.4461 0.5843 1.0123 0.031 Uiso 1 1 calc R . .
C18 C 0.6032(2) 0.6798(2) 0.94888(18) 0.0217(4) Uani 1 1 d . . .
H18 H 0.6771 0.6179 1.0074 0.026 Uiso 1 1 calc R . .
N1 N 0.82742(15) 0.66480(17) 0.75404(13) 0.0135(3) Uani 1 1 d . . .
O1 O 0.50659(15) 0.54093(16) 0.51266(13) 0.0215(3) Uani 1 1 d . . .
O2 O 0.80935(15) 0.96652(15) 0.78332(13) 0.0209(3) Uani 1 1 d . . .
O3 O 0.90062(13) 0.78478(15) 0.98087(12) 0.0200(3) Uani 1 1 d . . .
S1 S 0.80372(4) 0.81387(5) 0.85113(4) 0.01427(10) Uani 1 1 d . . .


_geom_special_details            
;
All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 O1 1.218(2) . ?
C1 C5 1.464(2) . ?
C1 C2 1.535(2) . ?
C2 N1 1.485(2) . ?
C2 C6 1.522(2) . ?
C2 H2 1.0000 . ?
C3 N1 1.475(2) . ?
C3 C4 1.487(2) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 C5 1.333(3) . ?
C4 H4 0.9500 . ?
C5 H5 0.9500 . ?
C6 C7 1.395(2) . ?
C6 C11 1.397(2) . ?
C7 C8 1.392(2) . ?
C7 H7 0.9500 . ?
C8 C9 1.388(3) . ?
C8 H8 0.9500 . ?
C9 C10 1.389(3) . ?
C9 H9 0.9500 . ?
C10 C11 1.390(2) . ?
C10 H10 0.9500 . ?
C11 H11 0.9500 . ?
C12 C13 1.390(2) . ?
C12 C18 1.390(2) . ?
C12 S1 1.7670(16) . ?
C13 C14 1.391(3) . ?
C13 H13 0.9500 . ?
C14 C15 1.398(2) . ?
C14 H14 0.9500 . ?
C15 C17 1.394(3) . ?
C15 C16 1.510(3) . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C17 C18 1.391(3) . ?
C17 H17 0.9500 . ?
C18 H18 0.9500 . ?
N1 S1 1.6437(14) . ?
O2 S1 1.4365(13) . ?
O3 S1 1.4362(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
O1 C1 C5 122.79(16) . . ?
O1 C1 C2 119.53(15) . . ?
C5 C1 C2 117.60(15) . . ?
N1 C2 C6 114.22(13) . . ?
N1 C2 C1 111.73(13) . . ?
C6 C2 C1 109.91(12) . . ?
N1 C2 H2 106.9 . . ?
C6 C2 H2 106.9 . . ?
C1 C2 H2 106.9 . . ?
N1 C3 C4 114.02(14) . . ?
N1 C3 H3A 108.7 . . ?
C4 C3 H3A 108.7 . . ?
N1 C3 H3B 108.7 . . ?
C4 C3 H3B 108.7 . . ?
H3A C3 H3B 107.6 . . ?
C5 C4 C3 124.31(16) . . ?
C5 C4 H4 117.8 . . ?
C3 C4 H4 117.8 . . ?
C4 C5 C1 121.47(16) . . ?
C4 C5 H5 119.3 . . ?
C1 C5 H5 119.3 . . ?
C7 C6 C11 119.05(15) . . ?
C7 C6 C2 118.07(14) . . ?
C11 C6 C2 122.83(15) . . ?
C8 C7 C6 120.36(16) . . ?
C8 C7 H7 119.8 . . ?
C6 C7 H7 119.8 . . ?
C9 C8 C7 120.36(16) . . ?
C9 C8 H8 119.8 . . ?
C7 C8 H8 119.8 . . ?
C8 C9 C10 119.47(16) . . ?
C8 C9 H9 120.3 . . ?
C10 C9 H9 120.3 . . ?
C9 C10 C11 120.51(18) . . ?
C9 C10 H10 119.7 . . ?
C11 C10 H10 119.7 . . ?
C10 C11 C6 120.23(16) . . ?
C10 C11 H11 119.9 . . ?
C6 C11 H11 119.9 . . ?
C13 C12 C18 121.00(16) . . ?
C13 C12 S1 119.23(12) . . ?
C18 C12 S1 119.69(13) . . ?
C12 C13 C14 119.42(16) . . ?
C12 C13 H13 120.3 . . ?
C14 C13 H13 120.3 . . ?
C13 C14 C15 120.64(16) . . ?
C13 C14 H14 119.7 . . ?
C15 C14 H14 119.7 . . ?
C17 C15 C14 118.85(16) . . ?
C17 C15 C16 121.00(16) . . ?
C14 C15 C16 120.15(17) . . ?
C15 C16 H16A 109.5 . . ?
C15 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C15 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C18 C17 C15 121.15(17) . . ?
C18 C17 H17 119.4 . . ?
C15 C17 H17 119.4 . . ?
C12 C18 C17 118.94(17) . . ?
C12 C18 H18 120.5 . . ?
C17 C18 H18 120.5 . . ?
C3 N1 C2 119.59(13) . . ?
C3 N1 S1 117.96(11) . . ?
C2 N1 S1 114.63(11) . . ?
O3 S1 O2 119.83(8) . . ?
O3 S1 N1 106.78(7) . . ?
O2 S1 N1 106.75(7) . . ?
O3 S1 C12 108.96(7) . . ?
O2 S1 C12 107.28(8) . . ?
N1 S1 C12 106.52(7) . . ?

_diffrn_measured_fraction_theta_max 0.985
_diffrn_reflns_theta_full        28.57
_diffrn_measured_fraction_theta_full 0.985
_refine_diff_density_max         0.443
_refine_diff_density_min         -0.337
_refine_diff_density_rms         0.053
_database_code_depnum_ccdc_archive 'CCDC 917485'
#######################################################################
#
#                 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_ltp245
#TrackingRef '16429_web_deposit_cif_file_1_KohPengFeiJackson_1356499898.rac-3.cif'


_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         '2(C21 H22 F3 N O3), C4 H8 O2'
_chemical_formula_sum            'C23 H26 F3 N O4'
_chemical_formula_weight         437.45

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   P-1

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   12.6844(10)
_cell_length_b                   13.0079(9)
_cell_length_c                   13.5817(10)
_cell_angle_alpha                83.347(3)
_cell_angle_beta                 80.714(2)
_cell_angle_gamma                83.780(2)
_cell_volume                     2187.5(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    103(2)
_cell_measurement_reflns_used    6518
_cell_measurement_theta_min      2.77
_cell_measurement_theta_max      27.88

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.18
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.328
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             920
_exptl_absorpt_coefficient_mu    0.107
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9585
_exptl_absorpt_correction_T_max  0.9810
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      103(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  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            32539
_diffrn_reflns_av_R_equivalents  0.0519
_diffrn_reflns_av_sigmaI/netI    0.0617
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         1.53
_diffrn_reflns_theta_max         28.37
_reflns_number_total             10671
_reflns_number_gt                7221
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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.
;

_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)+(0.0963P)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         10671
_refine_ls_number_parameters     568
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0857
_refine_ls_R_factor_gt           0.0515
_refine_ls_wR_factor_ref         0.1710
_refine_ls_wR_factor_gt          0.1386
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_restrained_S_all      1.031
_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
C1 C 1.06914(14) 0.91493(14) 0.85056(14) 0.0181(4) Uani 1 1 d . . .
H1A H 1.0876 0.9503 0.7823 0.022 Uiso 1 1 calc R . .
H1B H 1.0770 0.9627 0.9001 0.022 Uiso 1 1 calc R . .
C2 C 0.95406(14) 0.88344(14) 0.86638(14) 0.0167(4) Uani 1 1 d . . .
H2 H 0.9284 0.8713 0.9400 0.020 Uiso 1 1 calc R . .
C3 C 0.97257(15) 0.77815(14) 0.82178(14) 0.0197(4) Uani 1 1 d . . .
H3A H 0.9175 0.7316 0.8544 0.024 Uiso 1 1 calc R . .
H3B H 0.9704 0.7878 0.7487 0.024 Uiso 1 1 calc R . .
C4 C 1.08436(14) 0.73365(14) 0.84339(14) 0.0172(4) Uani 1 1 d . . .
C5 C 1.07999(14) 0.65393(14) 0.93766(13) 0.0168(4) Uani 1 1 d . . .
H5 H 1.0443 0.5937 0.9231 0.020 Uiso 1 1 calc R . .
C6 C 1.25453(15) 0.56685(15) 0.87129(14) 0.0222(4) Uani 1 1 d . . .
H6A H 1.2230 0.5036 0.8602 0.027 Uiso 1 1 calc R . .
H6B H 1.3277 0.5455 0.8871 0.027 Uiso 1 1 calc R . .
C7 C 1.26221(15) 0.63996(15) 0.77547(14) 0.0217(4) Uani 1 1 d . . .
H7A H 1.2996 0.6021 0.7188 0.026 Uiso 1 1 calc R . .
H7B H 1.3047 0.6977 0.7819 0.026 Uiso 1 1 calc R . .
C8 C 1.15053(15) 0.68390(15) 0.75408(14) 0.0211(4) Uani 1 1 d . . .
H8A H 1.1577 0.7365 0.6952 0.025 Uiso 1 1 calc R . .
H8B H 1.1124 0.6272 0.7374 0.025 Uiso 1 1 calc R . .
C9 C 0.87650(14) 0.96305(14) 0.81993(14) 0.0170(4) Uani 1 1 d . . .
C10 C 0.79232(14) 1.01544(14) 0.88063(14) 0.0179(4) Uani 1 1 d . . .
C11 C 0.72337(15) 1.09251(15) 0.83768(15) 0.0228(4) Uani 1 1 d . . .
H11 H 0.6665 1.1275 0.8793 0.027 Uiso 1 1 calc R . .
C12 C 0.73727(15) 1.11838(15) 0.73476(15) 0.0233(4) Uani 1 1 d . . .
H12 H 0.6912 1.1716 0.7055 0.028 Uiso 1 1 calc R . .
C13 C 0.81898(15) 1.06557(15) 0.67574(14) 0.0214(4) Uani 1 1 d . . .
C14 C 0.77924(17) 1.05808(17) 0.51330(15) 0.0272(4) Uani 1 1 d . . .
C15 C 0.88799(14) 0.98936(15) 0.71647(14) 0.0190(4) Uani 1 1 d . . .
H15 H 0.9438 0.9544 0.6738 0.023 Uiso 1 1 calc R . .
C16 C 1.01576(14) 0.69418(14) 1.03134(13) 0.0172(4) Uani 1 1 d . . .
C17 C 0.91432(15) 0.66232(15) 1.06730(14) 0.0207(4) Uani 1 1 d . . .
H17 H 0.8843 0.6177 1.0308 0.025 Uiso 1 1 calc R . .
C18 C 0.85660(16) 0.69456(16) 1.15515(15) 0.0253(4) Uani 1 1 d . . .
H18 H 0.7875 0.6717 1.1788 0.030 Uiso 1 1 calc R . .
C19 C 0.89854(16) 0.75973(16) 1.20889(15) 0.0258(4) Uani 1 1 d . . .
H19 H 0.8588 0.7813 1.2697 0.031 Uiso 1 1 calc R . .
C20 C 0.99903(16) 0.79371(15) 1.17380(15) 0.0236(4) Uani 1 1 d . . .
H20 H 1.0279 0.8394 1.2100 0.028 Uiso 1 1 calc R . .
C22 C 1.05706(15) 0.76102(14) 1.08611(14) 0.0201(4) Uani 1 1 d . . .
H22 H 1.1260 0.7842 1.0626 0.024 Uiso 1 1 calc R . .
C23 C 0.55775(14) 0.67899(15) 0.74254(15) 0.0221(4) Uani 1 1 d . . .
H23A H 0.5809 0.6739 0.6700 0.027 Uiso 1 1 calc R . .
H23B H 0.5280 0.6133 0.7730 0.027 Uiso 1 1 calc R . .
C24 C 0.65275(14) 0.69871(14) 0.79285(14) 0.0188(4) Uani 1 1 d . . .
H24 H 0.6368 0.6769 0.8664 0.023 Uiso 1 1 calc R . .
C25 C 0.64853(14) 0.81803(14) 0.77625(15) 0.0194(4) Uani 1 1 d . . .
H25A H 0.6760 0.8461 0.8310 0.023 Uiso 1 1 calc R . .
H25B H 0.6917 0.8408 0.7115 0.023 Uiso 1 1 calc R . .
C26 C 0.52944(14) 0.85430(14) 0.77596(14) 0.0177(4) Uani 1 1 d . . .
C27 C 0.47233(14) 0.88942(14) 0.87801(14) 0.0175(4) Uani 1 1 d . . .
H27 H 0.5062 0.9519 0.8899 0.021 Uiso 1 1 calc R . .
C28 C 0.33987(15) 1.00385(15) 0.79473(14) 0.0212(4) Uani 1 1 d . . .
H28A H 0.3699 1.0674 0.8074 0.025 Uiso 1 1 calc R . .
H28B H 0.2619 1.0206 0.7946 0.025 Uiso 1 1 calc R . .
C29 C 0.39167(16) 0.97248(16) 0.69267(15) 0.0237(4) Uani 1 1 d . . .
H29A H 0.3823 1.0315 0.6409 0.028 Uiso 1 1 calc R . .
H29B H 0.3564 0.9138 0.6761 0.028 Uiso 1 1 calc R . .
C30 C 0.51098(16) 0.94035(15) 0.69270(15) 0.0236(4) Uani 1 1 d . . .
H30A H 0.5429 0.9159 0.6271 0.028 Uiso 1 1 calc R . .
H30B H 0.5474 1.0014 0.7018 0.028 Uiso 1 1 calc R . .
C31 C 0.75612(14) 0.64065(14) 0.75022(14) 0.0178(4) Uani 1 1 d . . .
C32 C 0.80527(14) 0.55910(14) 0.80926(14) 0.0177(4) Uani 1 1 d . . .
C33 C 0.89928(15) 0.50255(15) 0.76824(15) 0.0211(4) Uani 1 1 d . . .
H33 H 0.9319 0.4471 0.8082 0.025 Uiso 1 1 calc R . .
C34 C 0.94506(15) 0.52710(15) 0.66944(14) 0.0214(4) Uani 1 1 d . . .
H34 H 1.0087 0.4889 0.6413 0.026 Uiso 1 1 calc R . .
C35 C 0.89640(15) 0.60780(15) 0.61316(14) 0.0204(4) Uani 1 1 d . . .
C36 C 1.00764(16) 0.70451(17) 0.49158(15) 0.0260(4) Uani 1 1 d . . .
C37 C 0.80303(14) 0.66354(15) 0.65144(14) 0.0197(4) Uani 1 1 d . . .
H37 H 0.7706 0.7178 0.6101 0.024 Uiso 1 1 calc R . .
C38 C 0.48568(14) 0.80843(14) 0.96562(14) 0.0182(4) Uani 1 1 d . . .
C39 C 0.42981(15) 0.71968(15) 0.98219(15) 0.0220(4) Uani 1 1 d . . .
H39 H 0.3827 0.7095 0.9371 0.026 Uiso 1 1 calc R . .
C40 C 0.44156(16) 0.64652(16) 1.06263(15) 0.0261(4) Uani 1 1 d . . .
H40 H 0.4029 0.5866 1.0724 0.031 Uiso 1 1 calc R . .
C41 C 0.50976(17) 0.66027(17) 1.12932(15) 0.0278(5) Uani 1 1 d . . .
H41 H 0.5174 0.6106 1.1854 0.033 Uiso 1 1 calc R . .
C42 C 0.56651(16) 0.74710(16) 1.11331(16) 0.0273(5) Uani 1 1 d . . .
H42 H 0.6140 0.7564 1.1583 0.033 Uiso 1 1 calc R . .
C43 C 0.55504(15) 0.82072(15) 1.03255(15) 0.0225(4) Uani 1 1 d . . .
H43 H 0.5947 0.8800 1.0226 0.027 Uiso 1 1 calc R . .
C44 C 0.3269(2) 0.5754(2) 0.39974(19) 0.0433(6) Uani 1 1 d . . .
H44A H 0.2873 0.5357 0.3633 0.065 Uiso 1 1 calc R . .
H44B H 0.4010 0.5773 0.3656 0.065 Uiso 1 1 calc R . .
H44C H 0.2925 0.6464 0.4019 0.065 Uiso 1 1 calc R . .
C45 C 0.3269(2) 0.52459(19) 0.50428(19) 0.0425(6) Uani 1 1 d . . .
H45A H 0.3654 0.5648 0.5423 0.051 Uiso 1 1 calc R . .
H45B H 0.2523 0.5212 0.5392 0.051 Uiso 1 1 calc R . .
C46 C 0.3883(2) 0.3627(2) 0.58395(19) 0.0388(6) Uani 1 1 d . . .
C47 C 0.4424(3) 0.2569(2) 0.5665(3) 0.0741(10) Uani 1 1 d . . .
H47A H 0.3915 0.2144 0.5468 0.111 Uiso 1 1 calc R . .
H47B H 0.4671 0.2238 0.6283 0.111 Uiso 1 1 calc R . .
H47C H 0.5039 0.2631 0.5131 0.111 Uiso 1 1 calc R . .
F1 F 0.82022(11) 1.07956(12) 0.41898(9) 0.0397(3) Uani 1 1 d . . .
F2 F 0.67817(10) 1.10129(13) 0.52615(10) 0.0470(4) Uani 1 1 d . . .
F3 F 0.77175(12) 0.95644(11) 0.53075(10) 0.0450(4) Uani 1 1 d . . .
F4 F 1.09558(11) 0.67792(14) 0.53310(10) 0.0538(4) Uani 1 1 d . . .
F5 F 0.96657(14) 0.79386(11) 0.52584(13) 0.0642(5) Uani 1 1 d . . .
F6 F 1.03780(10) 0.72001(11) 0.39462(9) 0.0374(3) Uani 1 1 d . . .
N1 N 1.18900(12) 0.61345(12) 0.95809(12) 0.0192(3) Uani 1 1 d . . .
H1N H 1.2236(18) 0.6687(18) 0.9697(16) 0.029 Uiso 1 1 d . . .
N2 N 0.35689(12) 0.92135(13) 0.87666(12) 0.0196(3) Uani 1 1 d . . .
H2N H 0.3240(18) 0.8642(18) 0.8674(16) 0.029 Uiso 1 1 d . . .
O1 O 1.13745(10) 0.82078(9) 0.86360(10) 0.0178(3) Uani 1 1 d . . .
O2 O 0.78153(11) 0.98816(11) 0.98078(10) 0.0231(3) Uani 1 1 d . . .
H2C H 0.7351 1.0298 1.0103 0.035 Uiso 1 1 calc R . .
O3 O 0.83983(11) 1.09382(11) 0.57068(10) 0.0267(3) Uani 1 1 d . . .
O4 O 0.47916(10) 0.76505(10) 0.75807(10) 0.0200(3) Uani 1 1 d . . .
O5 O 0.75853(11) 0.53946(11) 0.90544(10) 0.0242(3) Uani 1 1 d . . .
H5A H 0.7944 0.4900 0.9339 0.036 Uiso 1 1 calc R . .
O6 O 0.93933(11) 0.63092(11) 0.51070(10) 0.0239(3) Uani 1 1 d . . .
O7 O 0.38008(14) 0.42073(13) 0.49745(12) 0.0404(4) Uani 1 1 d . . .
O8 O 0.35662(15) 0.39340(16) 0.66490(13) 0.0513(5) Uani 1 1 d . . .


_geom_special_details            
;
All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 O1 1.432(2) . ?
C1 C2 1.534(2) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C2 C9 1.505(2) . ?
C2 C3 1.541(2) . ?
C2 H2 1.0000 . ?
C3 C4 1.533(2) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 O1 1.453(2) . ?
C4 C8 1.526(3) . ?
C4 C5 1.549(3) . ?
C5 N1 1.483(2) . ?
C5 C16 1.511(2) . ?
C5 H5 1.0000 . ?
C6 N1 1.479(2) . ?
C6 C7 1.517(3) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 C8 1.529(3) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 C15 1.395(3) . ?
C9 C10 1.405(3) . ?
C10 O2 1.354(2) . ?
C10 C11 1.396(3) . ?
C11 C12 1.387(3) . ?
C11 H11 0.9500 . ?
C12 C13 1.376(3) . ?
C12 H12 0.9500 . ?
C13 C15 1.377(3) . ?
C13 O3 1.421(2) . ?
C14 F1 1.313(2) . ?
C14 F3 1.327(3) . ?
C14 O3 1.330(2) . ?
C14 F2 1.336(2) . ?
C15 H15 0.9500 . ?
C16 C17 1.390(3) . ?
C16 C22 1.399(2) . ?
C17 C18 1.380(3) . ?
C17 H17 0.9500 . ?
C18 C19 1.379(3) . ?
C18 H18 0.9500 . ?
C19 C20 1.387(3) . ?
C19 H19 0.9500 . ?
C20 C22 1.381(3) . ?
C20 H20 0.9500 . ?
C22 H22 0.9500 . ?
C23 O4 1.427(2) . ?
C23 C24 1.536(2) . ?
C23 H23A 0.9900 . ?
C23 H23B 0.9900 . ?
C24 C31 1.506(3) . ?
C24 C25 1.539(3) . ?
C24 H24 1.0000 . ?
C25 C26 1.533(2) . ?
C25 H25A 0.9900 . ?
C25 H25B 0.9900 . ?
C26 O4 1.446(2) . ?
C26 C30 1.524(3) . ?
C26 C27 1.551(3) . ?
C27 N2 1.481(2) . ?
C27 C38 1.513(3) . ?
C27 H27 1.0000 . ?
C28 N2 1.479(2) . ?
C28 C29 1.516(3) . ?
C28 H28A 0.9900 . ?
C28 H28B 0.9900 . ?
C29 C30 1.526(3) . ?
C29 H29A 0.9900 . ?
C29 H29B 0.9900 . ?
C30 H30A 0.9900 . ?
C30 H30B 0.9900 . ?
C31 C37 1.390(3) . ?
C31 C32 1.406(3) . ?
C32 O5 1.352(2) . ?
C32 C33 1.401(3) . ?
C33 C34 1.389(3) . ?
C33 H33 0.9500 . ?
C34 C35 1.376(3) . ?
C34 H34 0.9500 . ?
C35 C37 1.379(3) . ?
C35 O6 1.420(2) . ?
C36 F6 1.309(2) . ?
C36 F5 1.325(2) . ?
C36 F4 1.325(2) . ?
C36 O6 1.336(2) . ?
C37 H37 0.9500 . ?
C38 C43 1.396(3) . ?
C38 C39 1.397(3) . ?
C39 C40 1.379(3) . ?
C39 H39 0.9500 . ?
C40 C41 1.387(3) . ?
C40 H40 0.9500 . ?
C41 C42 1.382(3) . ?
C41 H41 0.9500 . ?
C42 C43 1.385(3) . ?
C42 H42 0.9500 . ?
C43 H43 0.9500 . ?
C44 C45 1.495(3) . ?
C44 H44A 0.9800 . ?
C44 H44B 0.9800 . ?
C44 H44C 0.9800 . ?
C45 O7 1.449(3) . ?
C45 H45A 0.9900 . ?
C45 H45B 0.9900 . ?
C46 O8 1.206(3) . ?
C46 O7 1.334(3) . ?
C46 C47 1.496(4) . ?
C47 H47A 0.9800 . ?
C47 H47B 0.9800 . ?
C47 H47C 0.9800 . ?
N1 H1N 0.92(2) . ?
N2 H2N 0.92(2) . ?
O2 H2C 0.8400 . ?
O5 H5A 0.8400 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 C1 C2 106.41(14) . . ?
O1 C1 H1A 110.4 . . ?
C2 C1 H1A 110.4 . . ?
O1 C1 H1B 110.4 . . ?
C2 C1 H1B 110.4 . . ?
H1A C1 H1B 108.6 . . ?
C9 C2 C1 113.65(15) . . ?
C9 C2 C3 115.40(15) . . ?
C1 C2 C3 100.72(14) . . ?
C9 C2 H2 108.9 . . ?
C1 C2 H2 108.9 . . ?
C3 C2 H2 108.9 . . ?
C4 C3 C2 104.46(14) . . ?
C4 C3 H3A 110.9 . . ?
C2 C3 H3A 110.9 . . ?
C4 C3 H3B 110.9 . . ?
C2 C3 H3B 110.9 . . ?
H3A C3 H3B 108.9 . . ?
O1 C4 C8 108.94(14) . . ?
O1 C4 C3 106.33(14) . . ?
C8 C4 C3 112.05(15) . . ?
O1 C4 C5 107.37(13) . . ?
C8 C4 C5 109.38(15) . . ?
C3 C4 C5 112.56(15) . . ?
N1 C5 C16 109.21(14) . . ?
N1 C5 C4 111.56(14) . . ?
C16 C5 C4 114.33(15) . . ?
N1 C5 H5 107.1 . . ?
C16 C5 H5 107.1 . . ?
C4 C5 H5 107.1 . . ?
N1 C6 C7 113.27(16) . . ?
N1 C6 H6A 108.9 . . ?
C7 C6 H6A 108.9 . . ?
N1 C6 H6B 108.9 . . ?
C7 C6 H6B 108.9 . . ?
H6A C6 H6B 107.7 . . ?
C6 C7 C8 110.67(15) . . ?
C6 C7 H7A 109.5 . . ?
C8 C7 H7A 109.5 . . ?
C6 C7 H7B 109.5 . . ?
C8 C7 H7B 109.5 . . ?
H7A C7 H7B 108.1 . . ?
C4 C8 C7 112.05(15) . . ?
C4 C8 H8A 109.2 . . ?
C7 C8 H8A 109.2 . . ?
C4 C8 H8B 109.2 . . ?
C7 C8 H8B 109.2 . . ?
H8A C8 H8B 107.9 . . ?
C15 C9 C10 118.22(17) . . ?
C15 C9 C2 121.33(16) . . ?
C10 C9 C2 120.42(16) . . ?
O2 C10 C11 122.22(17) . . ?
O2 C10 C9 117.48(16) . . ?
C11 C10 C9 120.30(17) . . ?
C12 C11 C10 120.47(18) . . ?
C12 C11 H11 119.8 . . ?
C10 C11 H11 119.8 . . ?
C13 C12 C11 118.82(18) . . ?
C13 C12 H12 120.6 . . ?
C11 C12 H12 120.6 . . ?
C12 C13 C15 121.70(18) . . ?
C12 C13 O3 120.54(17) . . ?
C15 C13 O3 117.59(17) . . ?
F1 C14 F3 108.62(17) . . ?
F1 C14 O3 108.60(17) . . ?
F3 C14 O3 113.62(17) . . ?
F1 C14 F2 107.87(17) . . ?
F3 C14 F2 105.21(17) . . ?
O3 C14 F2 112.68(18) . . ?
C13 C15 C9 120.48(18) . . ?
C13 C15 H15 119.8 . . ?
C9 C15 H15 119.8 . . ?
C17 C16 C22 118.09(17) . . ?
C17 C16 C5 120.19(16) . . ?
C22 C16 C5 121.69(16) . . ?
C18 C17 C16 120.96(18) . . ?
C18 C17 H17 119.5 . . ?
C16 C17 H17 119.5 . . ?
C19 C18 C17 120.41(18) . . ?
C19 C18 H18 119.8 . . ?
C17 C18 H18 119.8 . . ?
C18 C19 C20 119.69(19) . . ?
C18 C19 H19 120.2 . . ?
C20 C19 H19 120.2 . . ?
C22 C20 C19 119.90(18) . . ?
C22 C20 H20 120.0 . . ?
C19 C20 H20 120.0 . . ?
C20 C22 C16 120.94(17) . . ?
C20 C22 H22 119.5 . . ?
C16 C22 H22 119.5 . . ?
O4 C23 C24 106.58(14) . . ?
O4 C23 H23A 110.4 . . ?
C24 C23 H23A 110.4 . . ?
O4 C23 H23B 110.4 . . ?
C24 C23 H23B 110.4 . . ?
H23A C23 H23B 108.6 . . ?
C31 C24 C23 112.47(15) . . ?
C31 C24 C25 115.96(15) . . ?
C23 C24 C25 100.91(15) . . ?
C31 C24 H24 109.0 . . ?
C23 C24 H24 109.0 . . ?
C25 C24 H24 109.0 . . ?
C26 C25 C24 104.71(14) . . ?
C26 C25 H25A 110.8 . . ?
C24 C25 H25A 110.8 . . ?
C26 C25 H25B 110.8 . . ?
C24 C25 H25B 110.8 . . ?
H25A C25 H25B 108.9 . . ?
O4 C26 C30 107.91(14) . . ?
O4 C26 C25 106.26(14) . . ?
C30 C26 C25 112.77(15) . . ?
O4 C26 C27 107.10(14) . . ?
C30 C26 C27 109.43(15) . . ?
C25 C26 C27 113.04(15) . . ?
N2 C27 C38 109.68(15) . . ?
N2 C27 C26 112.01(14) . . ?
C38 C27 C26 113.32(15) . . ?
N2 C27 H27 107.2 . . ?
C38 C27 H27 107.2 . . ?
C26 C27 H27 107.2 . . ?
N2 C28 C29 112.53(16) . . ?
N2 C28 H28A 109.1 . . ?
C29 C28 H28A 109.1 . . ?
N2 C28 H28B 109.1 . . ?
C29 C28 H28B 109.1 . . ?
H28A C28 H28B 107.8 . . ?
C28 C29 C30 110.14(15) . . ?
C28 C29 H29A 109.6 . . ?
C30 C29 H29A 109.6 . . ?
C28 C29 H29B 109.6 . . ?
C30 C29 H29B 109.6 . . ?
H29A C29 H29B 108.1 . . ?
C26 C30 C29 111.44(16) . . ?
C26 C30 H30A 109.3 . . ?
C29 C30 H30A 109.3 . . ?
C26 C30 H30B 109.3 . . ?
C29 C30 H30B 109.3 . . ?
H30A C30 H30B 108.0 . . ?
C37 C31 C32 118.56(16) . . ?
C37 C31 C24 121.20(16) . . ?
C32 C31 C24 120.20(16) . . ?
O5 C32 C33 122.66(17) . . ?
O5 C32 C31 117.23(16) . . ?
C33 C32 C31 120.11(17) . . ?
C34 C33 C32 120.35(18) . . ?
C34 C33 H33 119.8 . . ?
C32 C33 H33 119.8 . . ?
C35 C34 C33 118.70(17) . . ?
C35 C34 H34 120.7 . . ?
C33 C34 H34 120.7 . . ?
C34 C35 C37 121.98(18) . . ?
C34 C35 O6 119.44(17) . . ?
C37 C35 O6 118.46(17) . . ?
F6 C36 F5 109.12(18) . . ?
F6 C36 F4 107.16(16) . . ?
F5 C36 F4 105.44(18) . . ?
F6 C36 O6 109.12(16) . . ?
F5 C36 O6 113.27(17) . . ?
F4 C36 O6 112.50(18) . . ?
C35 C37 C31 120.28(18) . . ?
C35 C37 H37 119.9 . . ?
C31 C37 H37 119.9 . . ?
C43 C38 C39 118.00(18) . . ?
C43 C38 C27 120.42(17) . . ?
C39 C38 C27 121.58(16) . . ?
C40 C39 C38 121.36(17) . . ?
C40 C39 H39 119.3 . . ?
C38 C39 H39 119.3 . . ?
C39 C40 C41 120.08(19) . . ?
C39 C40 H40 120.0 . . ?
C41 C40 H40 120.0 . . ?
C42 C41 C40 119.2(2) . . ?
C42 C41 H41 120.4 . . ?
C40 C41 H41 120.4 . . ?
C41 C42 C43 120.87(18) . . ?
C41 C42 H42 119.6 . . ?
C43 C42 H42 119.6 . . ?
C42 C43 C38 120.44(19) . . ?
C42 C43 H43 119.8 . . ?
C38 C43 H43 119.8 . . ?
C45 C44 H44A 109.5 . . ?
C45 C44 H44B 109.5 . . ?
H44A C44 H44B 109.5 . . ?
C45 C44 H44C 109.5 . . ?
H44A C44 H44C 109.5 . . ?
H44B C44 H44C 109.5 . . ?
O7 C45 C44 107.49(19) . . ?
O7 C45 H45A 110.2 . . ?
C44 C45 H45A 110.2 . . ?
O7 C45 H45B 110.2 . . ?
C44 C45 H45B 110.2 . . ?
H45A C45 H45B 108.5 . . ?
O8 C46 O7 123.4(2) . . ?
O8 C46 C47 125.4(2) . . ?
O7 C46 C47 111.2(2) . . ?
C46 C47 H47A 109.5 . . ?
C46 C47 H47B 109.5 . . ?
H47A C47 H47B 109.5 . . ?
C46 C47 H47C 109.5 . . ?
H47A C47 H47C 109.5 . . ?
H47B C47 H47C 109.5 . . ?
C6 N1 C5 112.23(14) . . ?
C6 N1 H1N 106.7(14) . . ?
C5 N1 H1N 108.0(14) . . ?
C28 N2 C27 111.71(15) . . ?
C28 N2 H2N 108.8(14) . . ?
C27 N2 H2N 108.4(14) . . ?
C1 O1 C4 109.57(13) . . ?
C10 O2 H2C 109.5 . . ?
C14 O3 C13 117.80(15) . . ?
C23 O4 C26 110.13(13) . . ?
C32 O5 H5A 109.5 . . ?
C36 O6 C35 115.77(14) . . ?
C46 O7 C45 116.49(19) . . ?

_diffrn_measured_fraction_theta_max 0.975
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.978
_refine_diff_density_max         0.454
_refine_diff_density_min         -0.452
_refine_diff_density_rms         0.101
_database_code_depnum_ccdc_archive 'CCDC 917486'
#######################################################################
#
#                 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_ltp253
#TrackingRef '16430_web_deposit_cif_file_2_KohPengFeiJackson_1356499898.rac-6.cif'


_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C18 H17 N O4 S'
_chemical_formula_sum            'C18 H17 N O4 S'
_chemical_formula_weight         343.39

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P2(1)/n

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                   8.3044(14)
_cell_length_b                   10.7213(19)
_cell_length_c                   17.956(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 91.819(5)
_cell_angle_gamma                90.00
_cell_volume                     1597.9(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    103(2)
_cell_measurement_reflns_used    557
_cell_measurement_theta_min      2.74
_cell_measurement_theta_max      20.32

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.04
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.427
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             720
_exptl_absorpt_coefficient_mu    0.225
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9480
_exptl_absorpt_correction_T_max  0.9911
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      103(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  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            6904
_diffrn_reflns_av_R_equivalents  0.0714
_diffrn_reflns_av_sigmaI/netI    0.0816
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         2.21
_diffrn_reflns_theta_max         25.01
_reflns_number_total             2732
_reflns_number_gt                1853
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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.
;

_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)+(0.1118P)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    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2732
_refine_ls_number_parameters     219
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0967
_refine_ls_R_factor_gt           0.0610
_refine_ls_wR_factor_ref         0.1963
_refine_ls_wR_factor_gt          0.1512
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_restrained_S_all      1.024
_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
C1 C 0.6259(6) 0.7907(4) 0.8244(2) 0.0346(11) Uani 1 1 d . . .
H1 H 0.6219 0.8561 0.8600 0.042 Uiso 1 1 calc R . .
C2 C 0.5847(6) 0.8140(5) 0.7494(3) 0.0440(13) Uani 1 1 d . . .
H2 H 0.5509 0.8951 0.7344 0.053 Uiso 1 1 calc R . .
C3 C 0.5930(6) 0.7195(5) 0.6973(3) 0.0441(13) Uani 1 1 d . . .
H3 H 0.5673 0.7359 0.6463 0.053 Uiso 1 1 calc R . .
C4 C 0.6388(6) 0.6013(5) 0.7197(3) 0.0435(13) Uani 1 1 d . . .
H4 H 0.6445 0.5360 0.6840 0.052 Uiso 1 1 calc R . .
C5 C 0.6765(6) 0.5775(4) 0.7939(2) 0.0346(11) Uani 1 1 d . . .
H5 H 0.7055 0.4955 0.8092 0.041 Uiso 1 1 calc R . .
C6 C 0.6722(5) 0.6729(4) 0.8464(2) 0.0230(9) Uani 1 1 d . . .
C7 C 0.7202(5) 0.6425(4) 0.9274(2) 0.0220(9) Uani 1 1 d . . .
H7 H 0.6558 0.5680 0.9419 0.026 Uiso 1 1 calc R . .
C8 C 0.8969(5) 0.6050(4) 0.9337(2) 0.0241(10) Uani 1 1 d . . .
C9 C 1.0121(5) 0.6945(4) 0.9662(2) 0.0279(10) Uani 1 1 d . . .
H9 H 1.1234 0.6739 0.9674 0.033 Uiso 1 1 calc R . .
C10 C 0.9679(5) 0.8022(4) 0.9937(2) 0.0264(10) Uani 1 1 d . . .
H10 H 1.0502 0.8588 1.0094 0.032 Uiso 1 1 calc R . .
C11 C 0.7982(5) 0.8416(3) 1.0019(2) 0.0259(10) Uani 1 1 d . . .
H11 H 0.7830 0.8622 1.0555 0.031 Uiso 1 1 calc R . .
C12 C 0.5752(5) 0.6927(3) 1.1183(2) 0.0217(9) Uani 1 1 d . . .
C13 C 0.6657(6) 0.5863(4) 1.1287(2) 0.0324(11) Uani 1 1 d . . .
H13 H 0.6975 0.5388 1.0870 0.039 Uiso 1 1 calc R . .
C14 C 0.7102(6) 0.5490(4) 1.1998(2) 0.0362(12) Uani 1 1 d . . .
H14 H 0.7722 0.4752 1.2068 0.043 Uiso 1 1 calc R . .
C15 C 0.6660(6) 0.6173(4) 1.2614(2) 0.0313(11) Uani 1 1 d . . .
C16 C 0.7157(7) 0.5762(5) 1.3390(2) 0.0479(14) Uani 1 1 d . . .
H16A H 0.7810 0.6416 1.3632 0.072 Uiso 1 1 calc R . .
H16B H 0.7790 0.4993 1.3363 0.072 Uiso 1 1 calc R . .
H16C H 0.6194 0.5610 1.3678 0.072 Uiso 1 1 calc R . .
C17 C 0.5726(6) 0.7236(4) 1.2498(2) 0.0342(11) Uani 1 1 d . . .
H17 H 0.5394 0.7707 1.2914 0.041 Uiso 1 1 calc R . .
C18 C 0.5276(6) 0.7616(4) 1.1788(2) 0.0288(10) Uani 1 1 d . . .
H18 H 0.4644 0.8347 1.1715 0.035 Uiso 1 1 calc R . .
N1 N 0.6834(4) 0.7433(3) 0.98079(17) 0.0185(8) Uani 1 1 d . . .
O1 O 0.9393(4) 0.5051(3) 0.90871(17) 0.0365(8) Uani 1 1 d . . .
O2 O 0.7797(4) 0.9533(2) 0.96019(17) 0.0304(8) Uani 1 1 d . . .
H2A H 0.6998 0.9931 0.9752 0.046 Uiso 1 1 calc R . .
O3 O 0.4154(3) 0.6472(3) 0.99281(16) 0.0289(7) Uani 1 1 d . . .
O4 O 0.4612(4) 0.8664(3) 1.03186(17) 0.0344(8) Uani 1 1 d . . .
S1 S 0.51789(13) 0.74014(8) 1.02701(6) 0.0215(3) Uani 1 1 d . . .


_geom_special_details            
;
All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C6 1.375(6) . ?
C1 C2 1.402(6) . ?
C1 H1 0.9500 . ?
C2 C3 1.383(7) . ?
C2 H2 0.9500 . ?
C3 C4 1.380(7) . ?
C3 H3 0.9500 . ?
C4 C5 1.383(7) . ?
C4 H4 0.9500 . ?
C5 C6 1.392(6) . ?
C5 H5 0.9500 . ?
C6 C7 1.530(5) . ?
C7 N1 1.482(5) . ?
C7 C8 1.523(6) . ?
C7 H7 1.0000 . ?
C8 O1 1.218(5) . ?
C8 C9 1.463(6) . ?
C9 C10 1.313(6) . ?
C9 H9 0.9500 . ?
C10 C11 1.483(6) . ?
C10 H10 0.9500 . ?
C11 O2 1.418(5) . ?
C11 N1 1.463(5) . ?
C11 H11 1.0000 . ?
C12 C13 1.376(6) . ?
C12 C18 1.382(6) . ?
C12 S1 1.767(4) . ?
C13 C14 1.378(6) . ?
C13 H13 0.9500 . ?
C14 C15 1.386(6) . ?
C14 H14 0.9500 . ?
C15 C17 1.390(6) . ?
C15 C16 1.505(6) . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C17 C18 1.379(6) . ?
C17 H17 0.9500 . ?
C18 H18 0.9500 . ?
N1 S1 1.628(3) . ?
O2 H2A 0.8400 . ?
O3 S1 1.436(3) . ?
O4 S1 1.437(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C6 C1 C2 119.9(4) . . ?
C6 C1 H1 120.1 . . ?
C2 C1 H1 120.1 . . ?
C3 C2 C1 120.3(5) . . ?
C3 C2 H2 119.9 . . ?
C1 C2 H2 119.9 . . ?
C4 C3 C2 119.7(4) . . ?
C4 C3 H3 120.2 . . ?
C2 C3 H3 120.2 . . ?
C3 C4 C5 120.1(5) . . ?
C3 C4 H4 119.9 . . ?
C5 C4 H4 119.9 . . ?
C4 C5 C6 120.5(4) . . ?
C4 C5 H5 119.7 . . ?
C6 C5 H5 119.7 . . ?
C1 C6 C5 119.5(4) . . ?
C1 C6 C7 122.0(4) . . ?
C5 C6 C7 118.4(4) . . ?
N1 C7 C8 111.2(3) . . ?
N1 C7 C6 114.0(3) . . ?
C8 C7 C6 110.4(3) . . ?
N1 C7 H7 106.9 . . ?
C8 C7 H7 106.9 . . ?
C6 C7 H7 106.9 . . ?
O1 C8 C9 122.1(4) . . ?
O1 C8 C7 119.6(4) . . ?
C9 C8 C7 118.2(3) . . ?
C10 C9 C8 122.7(4) . . ?
C10 C9 H9 118.7 . . ?
C8 C9 H9 118.7 . . ?
C9 C10 C11 124.4(4) . . ?
C9 C10 H10 117.8 . . ?
C11 C10 H10 117.8 . . ?
O2 C11 N1 114.4(3) . . ?
O2 C11 C10 106.0(3) . . ?
N1 C11 C10 112.5(3) . . ?
O2 C11 H11 107.9 . . ?
N1 C11 H11 107.9 . . ?
C10 C11 H11 107.9 . . ?
C13 C12 C18 120.4(4) . . ?
C13 C12 S1 119.6(3) . . ?
C18 C12 S1 120.0(3) . . ?
C12 C13 C14 119.7(4) . . ?
C12 C13 H13 120.1 . . ?
C14 C13 H13 120.1 . . ?
C13 C14 C15 121.1(4) . . ?
C13 C14 H14 119.5 . . ?
C15 C14 H14 119.5 . . ?
C14 C15 C17 118.3(4) . . ?
C14 C15 C16 120.8(4) . . ?
C17 C15 C16 120.9(4) . . ?
C15 C16 H16A 109.5 . . ?
C15 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C15 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C18 C17 C15 121.0(4) . . ?
C18 C17 H17 119.5 . . ?
C15 C17 H17 119.5 . . ?
C17 C18 C12 119.5(4) . . ?
C17 C18 H18 120.2 . . ?
C12 C18 H18 120.2 . . ?
C11 N1 C7 123.1(3) . . ?
C11 N1 S1 115.9(2) . . ?
C7 N1 S1 120.6(3) . . ?
C11 O2 H2A 109.5 . . ?
O3 S1 O4 119.26(19) . . ?
O3 S1 N1 107.15(16) . . ?
O4 S1 N1 107.16(17) . . ?
O3 S1 C12 109.62(18) . . ?
O4 S1 C12 107.09(18) . . ?
N1 S1 C12 105.78(19) . . ?

_diffrn_measured_fraction_theta_max 0.972
_diffrn_reflns_theta_full        25.01
_diffrn_measured_fraction_theta_full 0.972
_refine_diff_density_max         0.477
_refine_diff_density_min         -0.434
_refine_diff_density_rms         0.122
_database_code_depnum_ccdc_archive 'CCDC 917487'
#######################################################################
#
#                 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_ltp242
#TrackingRef '16431_web_deposit_cif_file_3_KohPengFeiJackson_1356499898.rac-8.cif'


_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C20 H21 N O3 S'
_chemical_formula_sum            'C20 H21 N O3 S'
_chemical_formula_weight         355.44

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   P2(1)/n

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                   10.5854(6)
_cell_length_b                   16.1439(9)
_cell_length_c                   11.1053(6)
_cell_angle_alpha                90.00
_cell_angle_beta                 113.4850(10)
_cell_angle_gamma                90.00
_cell_volume                     1740.58(17)
_cell_formula_units_Z            4
_cell_measurement_temperature    103(2)
_cell_measurement_reflns_used    9399
_cell_measurement_theta_min      2.36
_cell_measurement_theta_max      31.01

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.38
_exptl_crystal_size_min          0.38
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.356
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             752
_exptl_absorpt_coefficient_mu    0.205
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9225
_exptl_absorpt_correction_T_max  0.9262
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      103(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  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            21129
_diffrn_reflns_av_R_equivalents  0.0333
_diffrn_reflns_av_sigmaI/netI    0.0303
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         3.22
_diffrn_reflns_theta_max         31.10
_reflns_number_total             5563
_reflns_number_gt                4794
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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.
;

_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)+(0.0494P)²+0.6249P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         5563
_refine_ls_number_parameters     228
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0439
_refine_ls_R_factor_gt           0.0368
_refine_ls_wR_factor_ref         0.1004
_refine_ls_wR_factor_gt          0.0958
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_restrained_S_all      1.044
_refine_ls_shift/su_max          0.002
_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
C1 C 0.28436(10) 0.29707(6) 1.14010(10) 0.01262(17) Uani 1 1 d . . .
H1 H 0.3698 0.2865 1.2205 0.015 Uiso 1 1 calc R . .
C2 C 0.22201(10) 0.37894(6) 1.16729(10) 0.01301(18) Uani 1 1 d . . .
C3 C 0.07297(11) 0.39114(6) 1.07014(10) 0.01457(18) Uani 1 1 d . . .
H3A H 0.0358 0.4424 1.0926 0.017 Uiso 1 1 calc R . .
H3B H 0.0702 0.3977 0.9805 0.017 Uiso 1 1 calc R . .
C4 C -0.01675(10) 0.31776(6) 1.07257(10) 0.01525(19) Uani 1 1 d . . .
H4A H -0.0218 0.3147 1.1596 0.018 Uiso 1 1 calc R . .
H4B H -0.1113 0.3260 1.0055 0.018 Uiso 1 1 calc R . .
C5 C 0.04134(10) 0.23687(6) 1.04541(10) 0.01400(18) Uani 1 1 d . . .
H5A H -0.0110 0.1896 1.0591 0.017 Uiso 1 1 calc R . .
H5B H 0.0313 0.2358 0.9529 0.017 Uiso 1 1 calc R . .
C6 C 0.33046(11) 0.30275(6) 1.02689(10) 0.01506(19) Uani 1 1 d . . .
C7 C 0.24335(12) 0.29876(7) 0.89424(11) 0.0201(2) Uani 1 1 d . . .
H7 H 0.1469 0.2929 0.8690 0.024 Uiso 1 1 calc R . .
C8 C 0.29689(15) 0.30333(8) 0.79825(13) 0.0280(3) Uani 1 1 d . . .
H8 H 0.2367 0.2996 0.7082 0.034 Uiso 1 1 calc R . .
C9 C 0.43703(16) 0.31329(8) 0.83297(15) 0.0331(3) Uani 1 1 d . . .
H9 H 0.4728 0.3174 0.7672 0.040 Uiso 1 1 calc R . .
C10 C 0.52432(15) 0.31713(9) 0.96435(16) 0.0338(3) Uani 1 1 d . . .
H10 H 0.6206 0.3237 0.9890 0.041 Uiso 1 1 calc R . .
C11 C 0.47161(12) 0.31148(8) 1.06032(13) 0.0238(2) Uani 1 1 d . . .
H11 H 0.5327 0.3136 1.1503 0.029 Uiso 1 1 calc R . .
C12 C 0.22903(11) 0.37681(6) 1.30330(10) 0.01578(19) Uani 1 1 d . . .
C13 C 0.23486(12) 0.38028(8) 1.41243(11) 0.0219(2) Uani 1 1 d . . .
H13 H 0.2395 0.3831 1.4996 0.026 Uiso 1 1 calc R . .
C14 C 0.25670(11) 0.09556(6) 1.01587(10) 0.01422(18) Uani 1 1 d . . .
C15 C 0.13746(11) 0.06365(7) 0.91836(11) 0.0169(2) Uani 1 1 d . . .
H15 H 0.0541 0.0609 0.9313 0.020 Uiso 1 1 calc R . .
C16 C 0.14235(11) 0.03590(7) 0.80177(11) 0.0185(2) Uani 1 1 d . . .
H16 H 0.0617 0.0136 0.7352 0.022 Uiso 1 1 calc R . .
C17 C 0.26372(12) 0.04019(6) 0.78096(11) 0.0179(2) Uani 1 1 d . . .
C18 C 0.26833(14) 0.01248(8) 0.65354(12) 0.0256(2) Uani 1 1 d . . .
H18A H 0.2783 0.0609 0.6048 0.038 Uiso 1 1 calc R . .
H18B H 0.1828 -0.0167 0.6011 0.038 Uiso 1 1 calc R . .
H18C H 0.3469 -0.0248 0.6716 0.038 Uiso 1 1 calc R . .
C19 C 0.38206(12) 0.07159(7) 0.88070(12) 0.0209(2) Uani 1 1 d . . .
H19 H 0.4657 0.0740 0.8682 0.025 Uiso 1 1 calc R . .
C20 C 0.37942(11) 0.09931(7) 0.99795(11) 0.0185(2) Uani 1 1 d . . .
H20 H 0.4605 0.1206 1.0653 0.022 Uiso 1 1 calc R . .
N1 N 0.18849(9) 0.22879(5) 1.13378(8) 0.01261(16) Uani 1 1 d . . .
O1 O 0.30806(8) 0.44289(5) 1.15450(8) 0.01795(16) Uani 1 1 d . . .
H1A H 0.3032 0.4844 1.1980 0.027 Uiso 1 1 calc R . .
O2 O 0.39088(9) 0.14163(5) 1.25711(8) 0.02171(18) Uani 1 1 d . . .
O3 O 0.15428(9) 0.08588(5) 1.19166(8) 0.02140(17) Uani 1 1 d . . .
S1 S 0.25191(3) 0.134884(15) 1.16165(2) 0.01460(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
C1 N1 1.4809(13) . ?
C1 C6 1.5219(14) . ?
C1 C2 1.5597(14) . ?
C1 H1 1.0000 . ?
C2 O1 1.4208(12) . ?
C2 C12 1.4827(15) . ?
C2 C3 1.5281(14) . ?
C3 C4 1.5252(15) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 C5 1.5239(14) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 N1 1.4792(13) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C6 C7 1.3936(15) . ?
C6 C11 1.3956(16) . ?
C7 C8 1.3944(16) . ?
C7 H7 0.9500 . ?
C8 C9 1.385(2) . ?
C8 H8 0.9500 . ?
C9 C10 1.383(2) . ?
C9 H9 0.9500 . ?
C10 C11 1.3891(18) . ?
C10 H10 0.9500 . ?
C11 H11 0.9500 . ?
C12 C13 1.1900(15) . ?
C13 H13 0.9500 . ?
C14 C20 1.3917(15) . ?
C14 C15 1.3934(14) . ?
C14 S1 1.7584(11) . ?
C15 C16 1.3904(15) . ?
C15 H15 0.9500 . ?
C16 C17 1.3949(16) . ?
C16 H16 0.9500 . ?
C17 C19 1.3955(16) . ?
C17 C18 1.5033(16) . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C19 C20 1.3876(16) . ?
C19 H19 0.9500 . ?
C20 H20 0.9500 . ?
N1 S1 1.6368(9) . ?
O1 H1A 0.8400 . ?
O2 S1 1.4341(8) . ?
O3 S1 1.4420(9) . ?

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
N1 C1 C6 116.42(8) . . ?
N1 C1 C2 107.76(8) . . ?
C6 C1 C2 114.12(8) . . ?
N1 C1 H1 105.9 . . ?
C6 C1 H1 105.9 . . ?
C2 C1 H1 105.9 . . ?
O1 C2 C12 110.17(8) . . ?
O1 C2 C3 111.00(8) . . ?
C12 C2 C3 109.92(9) . . ?
O1 C2 C1 104.99(8) . . ?
C12 C2 C1 108.92(8) . . ?
C3 C2 C1 111.71(8) . . ?
C4 C3 C2 111.24(8) . . ?
C4 C3 H3A 109.4 . . ?
C2 C3 H3A 109.4 . . ?
C4 C3 H3B 109.4 . . ?
C2 C3 H3B 109.4 . . ?
H3A C3 H3B 108.0 . . ?
C5 C4 C3 111.03(9) . . ?
C5 C4 H4A 109.4 . . ?
C3 C4 H4A 109.4 . . ?
C5 C4 H4B 109.4 . . ?
C3 C4 H4B 109.4 . . ?
H4A C4 H4B 108.0 . . ?
N1 C5 C4 110.21(8) . . ?
N1 C5 H5A 109.6 . . ?
C4 C5 H5A 109.6 . . ?
N1 C5 H5B 109.6 . . ?
C4 C5 H5B 109.6 . . ?
H5A C5 H5B 108.1 . . ?
C7 C6 C11 118.24(10) . . ?
C7 C6 C1 125.14(10) . . ?
C11 C6 C1 116.62(10) . . ?
C6 C7 C8 120.42(11) . . ?
C6 C7 H7 119.8 . . ?
C8 C7 H7 119.8 . . ?
C9 C8 C7 120.64(12) . . ?
C9 C8 H8 119.7 . . ?
C7 C8 H8 119.7 . . ?
C10 C9 C8 119.35(12) . . ?
C10 C9 H9 120.3 . . ?
C8 C9 H9 120.3 . . ?
C9 C10 C11 120.18(13) . . ?
C9 C10 H10 119.9 . . ?
C11 C10 H10 119.9 . . ?
C10 C11 C6 121.15(12) . . ?
C10 C11 H11 119.4 . . ?
C6 C11 H11 119.4 . . ?
C13 C12 C2 175.96(12) . . ?
C12 C13 H13 180.0 . . ?
C20 C14 C15 120.87(10) . . ?
C20 C14 S1 119.14(8) . . ?
C15 C14 S1 119.96(8) . . ?
C16 C15 C14 118.97(10) . . ?
C16 C15 H15 120.5 . . ?
C14 C15 H15 120.5 . . ?
C15 C16 C17 121.12(10) . . ?
C15 C16 H16 119.4 . . ?
C17 C16 H16 119.4 . . ?
C16 C17 C19 118.77(10) . . ?
C16 C17 C18 121.25(11) . . ?
C19 C17 C18 119.98(11) . . ?
C17 C18 H18A 109.5 . . ?
C17 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C17 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C20 C19 C17 120.97(10) . . ?
C20 C19 H19 119.5 . . ?
C17 C19 H19 119.5 . . ?
C19 C20 C14 119.29(10) . . ?
C19 C20 H20 120.4 . . ?
C14 C20 H20 120.4 . . ?
C5 N1 C1 119.10(8) . . ?
C5 N1 S1 116.82(7) . . ?
C1 N1 S1 117.31(7) . . ?
C2 O1 H1A 109.5 . . ?
O2 S1 O3 119.29(5) . . ?
O2 S1 N1 106.98(5) . . ?
O3 S1 N1 105.91(5) . . ?
O2 S1 C14 108.10(5) . . ?
O3 S1 C14 107.52(5) . . ?
N1 S1 C14 108.69(5) . . ?

_diffrn_measured_fraction_theta_max 0.994
_diffrn_reflns_theta_full        31.10
_diffrn_measured_fraction_theta_full 0.994
_refine_diff_density_max         0.471
_refine_diff_density_min         -0.476
_refine_diff_density_rms         0.059
_database_code_depnum_ccdc_archive 'CCDC 917488'
#######################################################################
#
#                 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_ltp254_0m
#TrackingRef '16432_web_deposit_cif_file_4_KohPengFeiJackson_1356499898.rac-10.cif'


_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_absolute_configuration ad
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C21 H23 N O3 S'
_chemical_formula_weight         369.46

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   P2(1)

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

_cell_length_a                   9.789(3)
_cell_length_b                   9.327(3)
_cell_length_c                   11.044(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 114.811(7)
_cell_angle_gamma                90.00
_cell_volume                     915.3(5)
_cell_formula_units_Z            2
_cell_measurement_temperature    103(2)
_cell_measurement_reflns_used    595
_cell_measurement_theta_min      2.98
_cell_measurement_theta_max      20.82

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.341
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             392
_exptl_absorpt_coefficient_mu    0.198
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9431
_exptl_absorpt_correction_T_max  0.9805
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      103(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  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            3585
_diffrn_reflns_av_R_equivalents  0.0000
_diffrn_reflns_av_sigmaI/netI    0.0810
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.03
_diffrn_reflns_theta_max         26.89
_reflns_number_total             3585
_reflns_number_gt                2960
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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.
;

_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)+(0.0926P)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    constr
_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   0.20(12)
_refine_ls_number_reflns         3585
_refine_ls_number_parameters     236
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0757
_refine_ls_R_factor_gt           0.0583
_refine_ls_wR_factor_ref         0.1581
_refine_ls_wR_factor_gt          0.1394
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_restrained_S_all      1.066
_refine_ls_shift/su_max          0.000
_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
C1 C 1.2309(4) 0.5583(5) 0.2439(4) 0.0225(9) Uani 1 1 d . . .
H1A H 1.1943 0.5889 0.3110 0.027 Uiso 1 1 calc R . .
H1B H 1.2425 0.6440 0.1962 0.027 Uiso 1 1 calc R . .
C2 C 1.3770(4) 0.4783(6) 0.3090(4) 0.0232(10) Uani 1 1 d . . .
H2 H 1.4700 0.5195 0.3678 0.028 Uiso 1 1 calc R . .
C3 C 1.3572(4) 0.3430(5) 0.2726(4) 0.0206(10) Uani 1 1 d . . .
H3 H 1.4342 0.2723 0.3002 0.025 Uiso 1 1 calc R . .
C4 C 1.1937(4) 0.3160(4) 0.1802(4) 0.0139(8) Uani 1 1 d . . .
C5 C 1.1671(4) 0.2427(5) 0.0483(4) 0.0186(9) Uani 1 1 d . . .
H5A H 1.2172 0.2984 0.0021 0.022 Uiso 1 1 calc R . .
H5B H 1.0579 0.2406 -0.0099 0.022 Uiso 1 1 calc R . .
C6 C 1.2288(4) 0.0894(5) 0.0719(4) 0.0207(10) Uani 1 1 d . . .
H6A H 1.2044 0.0426 -0.0152 0.025 Uiso 1 1 calc R . .
H6B H 1.3397 0.0926 0.1210 0.025 Uiso 1 1 calc R . .
C7 C 1.1638(4) 0.0010(5) 0.1506(4) 0.0166(8) Uani 1 1 d . . .
H7A H 1.0568 -0.0208 0.0939 0.020 Uiso 1 1 calc R . .
H7B H 1.2190 -0.0909 0.1776 0.020 Uiso 1 1 calc R . .
C8 C 1.1164(4) 0.2298(4) 0.2554(4) 0.0124(8) Uani 1 1 d . . .
H8 H 1.1563 0.2710 0.3475 0.015 Uiso 1 1 calc R . .
C9 C 0.9451(4) 0.2474(4) 0.1975(4) 0.0143(8) Uani 1 1 d . . .
C10 C 0.8412(4) 0.1678(5) 0.0925(4) 0.0189(9) Uani 1 1 d . . .
H10 H 0.8758 0.0982 0.0490 0.023 Uiso 1 1 calc R . .
C11 C 0.6875(4) 0.1889(5) 0.0506(4) 0.0236(10) Uani 1 1 d . . .
H11 H 0.6182 0.1322 -0.0199 0.028 Uiso 1 1 calc R . .
C12 C 0.6341(4) 0.2924(5) 0.1107(4) 0.0232(10) Uani 1 1 d . . .
H12 H 0.5290 0.3075 0.0812 0.028 Uiso 1 1 calc R . .
C13 C 0.7366(4) 0.3730(5) 0.2143(4) 0.0218(10) Uani 1 1 d . . .
H13 H 0.7018 0.4438 0.2565 0.026 Uiso 1 1 calc R . .
C14 C 0.8892(4) 0.3510(5) 0.2566(4) 0.0186(9) Uani 1 1 d . . .
H14 H 0.9580 0.4075 0.3275 0.022 Uiso 1 1 calc R . .
C15 C 0.9999(4) -0.0478(4) 0.3781(4) 0.0150(9) Uani 1 1 d . . .
C16 C 0.9251(4) -0.1683(5) 0.3046(4) 0.0175(9) Uani 1 1 d . . .
H16 H 0.9752 -0.2328 0.2702 0.021 Uiso 1 1 calc R . .
C17 C 0.7783(4) -0.1918(5) 0.2830(4) 0.0224(10) Uani 1 1 d . . .
H17 H 0.7275 -0.2734 0.2328 0.027 Uiso 1 1 calc R . .
C18 C 0.7014(4) -0.1007(5) 0.3320(4) 0.0222(10) Uani 1 1 d . . .
C19 C 0.5429(5) -0.1326(6) 0.3133(5) 0.0334(12) Uani 1 1 d . . .
H19A H 0.4841 -0.1668 0.2221 0.050 Uiso 1 1 calc R . .
H19B H 0.4969 -0.0452 0.3285 0.050 Uiso 1 1 calc R . .
H19C H 0.5447 -0.2066 0.3769 0.050 Uiso 1 1 calc R . .
C20 C 0.7763(4) 0.0209(5) 0.4036(4) 0.0202(10) Uani 1 1 d . . .
H20 H 0.7250 0.0859 0.4362 0.024 Uiso 1 1 calc R . .
C21 C 0.9256(4) 0.0472(5) 0.4274(4) 0.0185(9) Uani 1 1 d . . .
H21 H 0.9763 0.1292 0.4769 0.022 Uiso 1 1 calc R . .
N1 N 1.1759(3) 0.0807(4) 0.2709(3) 0.0141(7) Uani 1 1 d . . .
O1 O 1.1293(3) 0.4571(3) 0.1523(3) 0.0161(7) Uani 1 1 d . . .
O2 O 1.2586(3) -0.1444(3) 0.4027(3) 0.0204(7) Uani 1 1 d . . .
O3 O 1.2496(3) 0.0846(3) 0.5150(3) 0.0204(7) Uani 1 1 d . . .
S1 S 1.18531(9) -0.00965(11) 0.40188(9) 0.0146(2) Uani 1 1 d . . .


_geom_special_details            
;
All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 O1 1.435(5) . ?
C1 C2 1.502(6) . ?
C2 C3 1.314(7) . ?
C3 C4 1.515(5) . ?
C4 O1 1.436(5) . ?
C4 C5 1.529(5) . ?
C4 C8 1.561(5) . ?
C5 C6 1.531(6) . ?
C6 C7 1.518(6) . ?
C7 N1 1.483(5) . ?
C8 N1 1.490(5) . ?
C8 C9 1.532(5) . ?
C9 C10 1.393(6) . ?
C9 C14 1.399(6) . ?
C10 C11 1.390(5) . ?
C11 C12 1.392(6) . ?
C12 C13 1.385(6) . ?
C13 C14 1.381(5) . ?
C15 C21 1.394(6) . ?
C15 C16 1.400(6) . ?
C15 S1 1.758(4) . ?
C16 C17 1.373(5) . ?
C17 C18 1.387(6) . ?
C18 C20 1.401(6) . ?
C18 C19 1.506(6) . ?
C20 C21 1.393(5) . ?
N1 S1 1.643(3) . ?
O2 S1 1.445(3) . ?
O3 S1 1.439(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 C1 C2 104.4(4) . . ?
C3 C2 C1 110.0(4) . . ?
C2 C3 C4 110.1(4) . . ?
O1 C4 C3 103.7(3) . . ?
O1 C4 C5 108.8(3) . . ?
C3 C4 C5 115.2(3) . . ?
O1 C4 C8 108.6(3) . . ?
C3 C4 C8 109.7(3) . . ?
C5 C4 C8 110.5(3) . . ?
C4 C5 C6 111.0(3) . . ?
C7 C6 C5 112.0(3) . . ?
N1 C7 C6 110.2(4) . . ?
N1 C8 C9 117.0(3) . . ?
N1 C8 C4 106.8(3) . . ?
C9 C8 C4 114.4(3) . . ?
C10 C9 C14 117.7(3) . . ?
C10 C9 C8 125.4(3) . . ?
C14 C9 C8 116.9(3) . . ?
C11 C10 C9 120.8(4) . . ?
C10 C11 C12 120.7(4) . . ?
C13 C12 C11 118.9(4) . . ?
C14 C13 C12 120.3(4) . . ?
C13 C14 C9 121.7(4) . . ?
C21 C15 C16 120.4(4) . . ?
C21 C15 S1 119.2(3) . . ?
C16 C15 S1 120.3(3) . . ?
C17 C16 C15 118.9(4) . . ?
C16 C17 C18 122.3(4) . . ?
C17 C18 C20 118.4(4) . . ?
C17 C18 C19 121.4(4) . . ?
C20 C18 C19 120.2(4) . . ?
C21 C20 C18 120.6(4) . . ?
C20 C21 C15 119.5(4) . . ?
C7 N1 C8 119.0(3) . . ?
C7 N1 S1 119.1(3) . . ?
C8 N1 S1 117.1(2) . . ?
C1 O1 C4 109.9(3) . . ?
O3 S1 O2 119.41(17) . . ?
O3 S1 N1 107.07(18) . . ?
O2 S1 N1 107.20(17) . . ?
O3 S1 C15 107.54(17) . . ?
O2 S1 C15 107.66(18) . . ?
N1 S1 C15 107.44(16) . . ?

_diffrn_measured_fraction_theta_max 0.985
_diffrn_reflns_theta_full        26.89
_diffrn_measured_fraction_theta_full 0.985
_refine_diff_density_max         0.443
_refine_diff_density_min         -0.591
_refine_diff_density_rms         0.148


_database_code_depnum_ccdc_archive 'CCDC 917489'
