# Electronic Supplementary Material (ESI) for ChemComm.
# 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_I
_chemical_name_systematic        ?
_chemical_name_common            ALI-40-A
_chemical_formula_moiety         ?
_chemical_formula_sum            'C25 H33 B O7'
_chemical_formula_iupac          ?
_chemical_formula_weight         456.32

_chemical_melting_point          ?

_space_group_crystal_system      triclinic
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   9.5236(5)
_cell_length_b                   11.7389(8)
_cell_length_c                   12.5461(8)
_cell_angle_alpha                62.680(3)
_cell_angle_beta                 84.635(3)
_cell_angle_gamma                81.559(3)
_cell_volume                     1232.12(13)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    4086
_cell_measurement_theta_min      2.7904
_cell_measurement_theta_max      24.5451
_cell_measurement_temperature    296.(2)

_exptl_crystal_description       prismatic
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_size_max          0.240
_exptl_crystal_size_mid          0.190
_exptl_crystal_size_min          0.100
_exptl_crystal_density_diffrn    1.230
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             488

_exptl_absorpt_coefficient_mu    0.088
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_correction_T_min  0.89
_exptl_absorpt_correction_T_max  0.99

_exptl_special_details           
;
;

_diffrn_ambient_temperature      296.(2)

_diffrn_source                   ?
_diffrn_source_type              ?

_diffrn_radiation_type           ?
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  ?

_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?

_diffrn_detector_area_resol_mean 8.3333

_diffrn_reflns_number            16041
_diffrn_reflns_av_R_equivalents  0.0345
_diffrn_reflns_av_sigmaI/netI    0.0374
_diffrn_reflns_theta_min         1.83
_diffrn_reflns_theta_max         25.35
_diffrn_reflns_theta_full        25.35
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 0.994
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15

_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.
;

_reflns_number_total             4463
_reflns_number_gt                3099
_reflns_threshold_expression     >2sigma(I)

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0787
_refine_ls_R_factor_gt           0.0477
_refine_ls_wR_factor_gt          0.1441
_refine_ls_wR_factor_ref         0.1811
_refine_ls_goodness_of_fit_ref   1.004
_refine_ls_restrained_S_all      1.004
_refine_ls_number_reflns         4463
_refine_ls_number_parameters     305
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment    refxyz
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.1253P)²+0.0174P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap

_refine_ls_shift/su_max          0.018
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.290
_refine_diff_density_min         -0.306
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

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'
B B 0.0013 0.0007 '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'

_computing_data_collection       'Bruker Instrument Service v2010.9.0.0'
_computing_cell_refinement       'SAINT V7.68A (Bruker AXS, 2009)'
_computing_data_reduction        'SAINT V7.68A (Bruker AXS, 2009)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
B B1 0.2156(2) 0.7944(2) 0.1748(2) 0.0369(6) Uani d . 1 . .
C C1 0.1218(2) 0.89087(19) 0.21489(18) 0.0357(5) Uani d . 1 . .
C C2 0.1216(2) 1.03292(19) 0.13417(18) 0.0351(5) Uani d . 1 . .
C C3 0.1221(2) 1.1201(2) 0.1811(2) 0.0416(5) Uani d . 1 . .
H H3 0.1231 1.089 0.2639 0.05 Uiso calc R 1 . .
C C4 0.1211(2) 1.2509(2) 0.1086(2) 0.0464(6) Uani d . 1 . .
H H4 0.1195 1.3065 0.1429 0.056 Uiso calc R 1 . .
C C5 0.1223(2) 1.2998(2) -0.0150(2) 0.0413(5) Uani d . 1 . .
C C6 0.1236(2) 1.2161(2) -0.06482(19) 0.0396(5) Uani d . 1 . .
H H6 0.1236 1.2477 -0.1477 0.048 Uiso calc R 1 . .
C C7 0.1250(2) 1.0843(2) 0.00987(19) 0.0373(5) Uani d . 1 . .
H H7 0.1282 1.0287 -0.0246 0.045 Uiso calc R 1 . .
C C8 0.1329(3) 1.4841(2) -0.2069(2) 0.0633(7) Uani d . 1 . .
H H8A 0.2184 1.4458 -0.2305 0.095 Uiso calc R 1 . .
H H8B 0.1347 1.5757 -0.2409 0.095 Uiso calc R 1 . .
H H8C 0.0523 1.4668 -0.2353 0.095 Uiso calc R 1 . .
C C9 0.3634(2) 0.7260(2) 0.0564(2) 0.0441(6) Uani d . 1 . .
C C10 0.2822(3) 0.7583(3) -0.0545(2) 0.0628(7) Uani d . 1 . .
H H10A 0.182 0.765 -0.0364 0.094 Uiso calc R 1 . .
H H10B 0.3072 0.6913 -0.0789 0.094 Uiso calc R 1 . .
H H10C 0.306 0.8389 -0.1182 0.094 Uiso calc R 1 . .
C C11 0.5223(2) 0.7187(3) 0.0286(3) 0.0630(7) Uani d . 1 . .
H H11A 0.5428 0.7948 -0.0427 0.094 Uiso calc R 1 . .
H H11B 0.5529 0.6438 0.0163 0.094 Uiso calc R 1 . .
H H11C 0.5716 0.7128 0.0946 0.094 Uiso calc R 1 . .
C C12 0.3158(2) 0.6077(2) 0.1703(2) 0.0429(5) Uani d . 1 . .
C C13 0.2621(3) 0.5062(2) 0.1475(3) 0.0582(7) Uani d . 1 . .
H H13A 0.2332 0.4383 0.2223 0.087 Uiso calc R 1 . .
H H13B 0.3365 0.4713 0.1099 0.087 Uiso calc R 1 . .
H H13C 0.1826 0.5445 0.0958 0.087 Uiso calc R 1 . .
C C14 0.4267(3) 0.5431(3) 0.2681(3) 0.0602(7) Uani d . 1 . .
H H14A 0.4594 0.6075 0.2836 0.09 Uiso calc R 1 . .
H H14B 0.5054 0.5002 0.2417 0.09 Uiso calc R 1 . .
H H14C 0.3846 0.4812 0.3403 0.09 Uiso calc R 1 . .
C C15 0.0423(2) 0.84824(19) 0.31751(18) 0.0362(5) Uani d . 1 . .
C C16 -0.0711(2) 0.9282(2) 0.35599(19) 0.0399(5) Uani d . 1 . .
H H16A -0.1178 0.9989 0.287 0.048 Uiso calc R 1 . .
H H16B -0.0306 0.963 0.4014 0.048 Uiso calc R 1 . .
C C17 -0.1759(2) 0.83128(19) 0.43507(18) 0.0382(5) Uani d . 1 . .
C C18 -0.0739(2) 0.7083(2) 0.5047(2) 0.0463(6) Uani d . 1 . .
H H18A -0.0363 0.7111 0.5726 0.056 Uiso calc R 1 . .
H H18B -0.1225 0.6319 0.5339 0.056 Uiso calc R 1 . .
C C19 0.0461(2) 0.7071(2) 0.41383(19) 0.0425(5) Uani d . 1 . .
H H19 0.0224 0.6553 0.3765 0.051 Uiso calc R 1 . .
C C20 0.1853(3) 0.6483(3) 0.4737(2) 0.0596(7) Uani d . 1 . .
H H20 0.2035 0.5588 0.5072 0.072 Uiso calc R 1 . .
C C21 0.2813(3) 0.7064(3) 0.4841(3) 0.0809(9) Uani d . 1 . .
H H21A 0.2689 0.796 0.4524 0.097 Uiso calc R 1 . .
H H21B 0.3642 0.6596 0.5235 0.097 Uiso calc R 1 . .
C C22 -0.2646(2) 0.8745(2) 0.5196(2) 0.0452(6) Uani d . 1 . .
C C23 -0.4624(3) 0.8315(3) 0.6559(3) 0.0799(9) Uani d . 1 . .
H H23A -0.4123 0.8047 0.7281 0.12 Uiso calc R 1 . .
H H23B -0.5446 0.7865 0.6743 0.12 Uiso calc R 1 . .
H H23C -0.4914 0.9228 0.6214 0.12 Uiso calc R 1 . .
C C24 -0.2734(2) 0.8084(2) 0.35940(19) 0.0404(5) Uani d . 1 . .
C C25 -0.4610(3) 0.9055(3) 0.2237(3) 0.0713(8) Uani d . 1 . .
H H25A -0.4149 0.9078 0.1514 0.107 Uiso calc R 1 . .
H H25B -0.5349 0.9765 0.2036 0.107 Uiso calc R 1 . .
H H25C -0.5013 0.8257 0.2679 0.107 Uiso calc R 1 . .
O O1 0.12322(19) 1.43085(15) -0.07980(15) 0.0576(5) Uani d . 1 . .
O O2 0.19768(14) 0.66692(14) 0.21819(13) 0.0433(4) Uani d . 1 . .
O O3 0.32166(14) 0.83150(14) 0.08833(14) 0.0452(4) Uani d . 1 . .
O O4 -0.36994(19) 0.80208(17) 0.57097(16) 0.0639(5) Uani d . 1 . .
O O5 -0.2435(2) 0.9603(2) 0.54014(18) 0.0733(6) Uani d . 1 . .
O O6 -0.35850(17) 0.91520(15) 0.29605(15) 0.0544(5) Uani d . 1 . .
O O7 -0.27480(19) 0.70859(17) 0.35579(17) 0.0647(5) Uani d . 1 . .


_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_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
B1 O2 . 1.369(3) ?
B1 O3 . 1.370(3) ?
B1 C1 . 1.573(3) ?
C1 C15 . 1.349(3) ?
C1 C2 . 1.502(3) ?
C2 C7 . 1.389(3) ?
C2 C3 . 1.396(3) ?
C3 C4 . 1.378(3) ?
C4 C5 . 1.385(3) ?
C5 O1 . 1.372(3) ?
C5 C6 . 1.383(3) ?
C6 C7 . 1.392(3) ?
C8 O1 . 1.420(3) ?
C9 O3 . 1.461(3) ?
C9 C10 . 1.519(3) ?
C9 C11 . 1.520(3) ?
C9 C12 . 1.555(3) ?
C12 O2 . 1.462(2) ?
C12 C13 . 1.510(3) ?
C12 C14 . 1.533(3) ?
C15 C16 . 1.517(3) ?
C15 C19 . 1.536(3) ?
C16 C17 . 1.545(3) ?
C17 C22 . 1.515(3) ?
C17 C24 . 1.519(3) ?
C17 C18 . 1.543(3) ?
C18 C19 . 1.541(3) ?
C19 C20 . 1.496(3) ?
C20 C21 . 1.268(4) ?
C22 O5 . 1.195(3) ?
C22 O4 . 1.331(3) ?
C23 O4 . 1.450(3) ?
C24 O7 . 1.195(3) ?
C24 O6 . 1.330(3) ?
C25 O6 . 1.443(3) ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
O2 B1 O3 . . 112.73(19) ?
O2 B1 C1 . . 124.37(19) ?
O3 B1 C1 . . 122.86(19) ?
C15 C1 C2 . . 120.65(19) ?
C15 C1 B1 . . 121.46(19) ?
C2 C1 B1 . . 117.88(18) ?
C7 C2 C3 . . 116.44(19) ?
C7 C2 C1 . . 122.34(18) ?
C3 C2 C1 . . 121.20(18) ?
C4 C3 C2 . . 122.1(2) ?
C3 C4 C5 . . 120.2(2) ?
O1 C5 C6 . . 124.6(2) ?
O1 C5 C4 . . 116.1(2) ?
C6 C5 C4 . . 119.3(2) ?
C5 C6 C7 . . 119.6(2) ?
C2 C7 C6 . . 122.27(19) ?
O3 C9 C10 . . 106.81(19) ?
O3 C9 C11 . . 108.69(18) ?
C10 C9 C11 . . 110.3(2) ?
O3 C9 C12 . . 102.28(17) ?
C10 C9 C12 . . 113.45(19) ?
C11 C9 C12 . . 114.6(2) ?
O2 C12 C13 . . 108.48(17) ?
O2 C12 C14 . . 106.35(18) ?
C13 C12 C14 . . 109.6(2) ?
O2 C12 C9 . . 102.24(16) ?
C13 C12 C9 . . 115.4(2) ?
C14 C12 C9 . . 114.07(18) ?
C1 C15 C16 . . 126.75(19) ?
C1 C15 C19 . . 125.42(19) ?
C16 C15 C19 . . 107.76(17) ?
C15 C16 C17 . . 103.88(16) ?
C22 C17 C24 . . 109.41(18) ?
C22 C17 C18 . . 111.24(17) ?
C24 C17 C18 . . 110.62(18) ?
C22 C17 C16 . . 112.19(18) ?
C24 C17 C16 . . 111.53(17) ?
C18 C17 C16 . . 101.69(17) ?
C19 C18 C17 . . 105.38(17) ?
C20 C19 C15 . . 115.01(19) ?
C20 C19 C18 . . 111.49(19) ?
C15 C19 C18 . . 104.84(16) ?
C21 C20 C19 . . 127.5(3) ?
O5 C22 O4 . . 123.6(2) ?
O5 C22 C17 . . 125.6(2) ?
O4 C22 C17 . . 110.8(2) ?
O7 C24 O6 . . 123.6(2) ?
O7 C24 C17 . . 125.4(2) ?
O6 C24 C17 . . 110.97(18) ?
C5 O1 C8 . . 117.9(2) ?
B1 O2 C12 . . 107.37(16) ?
B1 O3 C9 . . 107.35(16) ?
C22 O4 C23 . . 116.8(2) ?
C24 O6 C25 . . 116.74(19) ?

_database_code_depnum_ccdc_archive 'CCDC 1005655'
#######################################################################
#
#                 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_I
_chemical_name_systematic        ?
_chemical_name_common            ARL628_RX
_chemical_formula_moiety         ?
_chemical_formula_sum            'C27 H33 B O6 S2'
_chemical_formula_iupac          ?
_chemical_formula_weight         528.46

_chemical_melting_point          ?

_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   8.1024(2)
_cell_length_b                   13.4762(3)
_cell_length_c                   25.6608(5)
_cell_angle_alpha                90
_cell_angle_beta                 96.5180(10)
_cell_angle_gamma                90
_cell_volume                     2783.78(11)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9994
_cell_measurement_theta_min      2.5301
_cell_measurement_theta_max      28.2887
_cell_measurement_temperature    296.(2)

_exptl_crystal_description       prismatic
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_size_max          0.190
_exptl_crystal_size_mid          0.060
_exptl_crystal_size_min          0.040
_exptl_crystal_density_diffrn    1.261
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1120

_exptl_absorpt_coefficient_mu    0.229
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_correction_T_min  0.89
_exptl_absorpt_correction_T_max  0.99

_exptl_special_details           
;
;

_diffrn_ambient_temperature      296.(2)

_diffrn_source                   ?
_diffrn_source_type              ?

_diffrn_radiation_type           ?
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  ?

_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?

_diffrn_detector_area_resol_mean 8.3333

_diffrn_reflns_number            50200
_diffrn_reflns_av_R_equivalents  0.0610
_diffrn_reflns_av_sigmaI/netI    0.0576
_diffrn_reflns_theta_min         1.60
_diffrn_reflns_theta_max         29.41
_diffrn_reflns_theta_full        29.41
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measured_fraction_theta_full 0.987
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -35
_diffrn_reflns_limit_l_max       35

_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.
;

_reflns_number_total             7595
_reflns_number_gt                4803
_reflns_threshold_expression     >2sigma(I)

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.1082
_refine_ls_R_factor_gt           0.0601
_refine_ls_wR_factor_gt          0.1482
_refine_ls_wR_factor_ref         0.1794
_refine_ls_goodness_of_fit_ref   1.018
_refine_ls_restrained_S_all      1.018
_refine_ls_number_reflns         7595
_refine_ls_number_parameters     331
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment    refxyz
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.1068P)²+0.0863P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap

_refine_ls_shift/su_max          0.010
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.611
_refine_diff_density_min         -0.528
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.0227(19)

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'
B B 0.0013 0.0007 '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'

_computing_data_collection       'Bruker Instrument Service v2010.9.0.0'
_computing_cell_refinement       'SAINT V7.68A (Bruker AXS, 2009)'
_computing_data_reduction        'SAINT V7.68A (Bruker AXS, 2009)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
B B1 0.1897(4) 0.2121(2) 0.06852(10) 0.0443(7) Uani d . 1 . .
C C1 -0.1771(3) 0.09438(16) 0.32814(8) 0.0318(5) Uani d . 1 . .
C C2 -0.1839(3) 0.00973(18) 0.35838(9) 0.0399(5) Uani d . 1 . .
H H2 -0.0912 -0.031 0.3648 0.048 Uiso calc R 1 . .
C C3 -0.3294(3) -0.01377(19) 0.37897(10) 0.0464(6) Uani d . 1 . .
H H3 -0.3345 -0.0699 0.3998 0.056 Uiso calc R 1 . .
C C4 -0.4671(3) 0.0464(2) 0.36844(10) 0.0476(6) Uani d . 1 . .
H H4 -0.5656 0.0297 0.3817 0.057 Uiso calc R 1 . .
C C5 -0.4602(3) 0.1307(2) 0.33864(10) 0.0476(6) Uani d . 1 . .
H H5 -0.5537 0.1708 0.332 0.057 Uiso calc R 1 . .
C C6 -0.3150(3) 0.15612(19) 0.31852(9) 0.0409(5) Uani d . 1 . .
H H6 -0.3094 0.2137 0.2988 0.049 Uiso calc R 1 . .
C C7 0.2183(3) -0.05079(17) 0.21057(9) 0.0366(5) Uani d . 1 . .
C C8 0.3324(3) -0.07204(19) 0.25342(10) 0.0454(6) Uani d . 1 . .
H H8 0.3018 -0.0694 0.2873 0.055 Uiso calc R 1 . .
C C9 0.4925(3) -0.0972(2) 0.24503(12) 0.0563(7) Uani d . 1 . .
H H9 0.5703 -0.1114 0.2735 0.068 Uiso calc R 1 . .
C C10 0.5384(3) -0.1014(2) 0.19506(13) 0.0598(8) Uani d . 1 . .
H H10 0.6469 -0.1177 0.1899 0.072 Uiso calc R 1 . .
C C11 0.4231(4) -0.0814(2) 0.15270(12) 0.0620(8) Uani d . 1 . .
H H11 0.4537 -0.0857 0.1189 0.074 Uiso calc R 1 . .
C C12 0.2626(3) -0.0550(2) 0.15988(10) 0.0477(6) Uani d . 1 . .
H H12 0.1854 -0.0403 0.1313 0.057 Uiso calc R 1 . .
C C16 -0.0668(3) 0.19527(16) 0.15130(8) 0.0340(5) Uani d . 1 . .
H H16 -0.105 0.1456 0.1247 0.041 Uiso calc R 1 . .
C C17 0.1229(3) 0.18911(16) 0.16313(8) 0.0325(5) Uani d . 1 . .
C C18 0.2354(3) 0.19775(18) 0.12881(8) 0.0382(5) Uani d . 1 . .
C C19 -0.1270(3) 0.29571(19) 0.13280(9) 0.0433(6) Uani d . 1 . .
H H19 -0.0935 0.3497 0.154 0.052 Uiso calc R 1 . .
C C20 -0.2232(4) 0.3140(3) 0.08923(12) 0.0704(9) Uani d . 1 . .
H H20A -0.2596 0.2621 0.0669 0.084 Uiso calc R 1 . .
H H20B -0.2549 0.3788 0.0806 0.084 Uiso calc R 1 . .
C C21 0.4205(3) 0.1938(2) 0.14633(10) 0.0515(7) Uani d . 1 . .
H H21A 0.4388 0.1924 0.184 0.077 Uiso calc R 1 . .
H H21B 0.4732 0.2513 0.1336 0.077 Uiso calc R 1 . .
H H21C 0.4667 0.1351 0.1325 0.077 Uiso calc R 1 . .
C C25 0.2099(5) 0.2703(4) -0.01379(11) 0.0952(14) Uani d . 1 . .
C C26 0.0813(5) 0.1925(3) -0.01638(11) 0.0938(14) Uani d . 1 . .
C C27 0.0125(3) 0.11562(15) 0.23691(7) 0.0301(5) Uani d . 1 . .
C C28 0.1652(3) 0.17130(17) 0.22113(7) 0.0322(5) Uani d . 1 . .
H H28A 0.1816 0.2335 0.24 0.039 Uiso calc R 1 . .
H H28B 0.2648 0.1313 0.228 0.039 Uiso calc R 1 . .
C C29 -0.1321(3) 0.16787(17) 0.20391(8) 0.0340(5) Uani d . 1 . .
H H29A -0.1649 0.2271 0.2216 0.041 Uiso calc R 1 . .
H H29B -0.2273 0.124 0.1979 0.041 Uiso calc R 1 . .
C C30 0.3411(7) 0.2688(5) -0.05040(16) 0.141(2) Uani d . 1 . .
H H30A 0.408 0.3275 -0.0453 0.212 Uiso calc R 1 . .
H H30B 0.2895 0.2666 -0.086 0.212 Uiso calc R 1 . .
H H30C 0.4099 0.2112 -0.0434 0.212 Uiso calc R 1 . .
C C31 -0.0830(7) 0.2042(5) -0.04733(15) 0.152(3) Uani d . 1 . .
H H31A -0.1526 0.149 -0.0408 0.228 Uiso calc R 1 . .
H H31B -0.0694 0.2066 -0.084 0.228 Uiso calc R 1 . .
H H31C -0.1337 0.2647 -0.0373 0.228 Uiso calc R 1 . .
C C32 0.1638(10) 0.0903(4) -0.03560(19) 0.189(3) Uani d . 1 . .
H H32A 0.2748 0.0837 -0.0184 0.283 Uiso calc R 1 . .
H H32B 0.1667 0.0924 -0.0729 0.283 Uiso calc R 1 . .
H H32C 0.0984 0.0346 -0.0268 0.283 Uiso calc R 1 . .
C C33 0.1204(9) 0.3739(4) -0.0179(2) 0.176(3) Uani d . 1 . .
H H33A 0.0193 0.37 -0.0018 0.264 Uiso calc R 1 . .
H H33B 0.0953 0.3917 -0.0542 0.264 Uiso calc R 1 . .
H H33C 0.1919 0.4231 -0.0003 0.264 Uiso calc R 1 . .
O O1 0.14358(19) 0.07004(14) 0.33320(6) 0.0441(4) Uani d . 1 . .
O O2 0.0256(2) 0.23751(13) 0.31635(6) 0.0470(4) Uani d . 1 . .
O O3 -0.0443(2) -0.07358(12) 0.26094(6) 0.0406(4) Uani d . 1 . .
O O4 -0.0830(2) -0.02359(12) 0.16785(6) 0.0414(4) Uani d . 1 . .
O O7 0.2918(3) 0.2630(2) 0.03985(7) 0.0812(7) Uani d . 1 . .
O O8 0.0565(3) 0.17544(19) 0.03875(7) 0.0809(8) Uani d . 1 . .
S S1 0.01122(6) -0.01762(4) 0.21858(2) 0.03183(16) Uani d . 1 . .
S S2 0.01429(7) 0.13213(4) 0.308099(19) 0.03276(17) Uani d . 1 . .


_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_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
B1 O8 . 1.344(4) ?
B1 O7 . 1.354(3) ?
B1 C18 . 1.561(3) ?
C1 C2 . 1.384(3) ?
C1 C6 . 1.393(3) ?
C1 S2 . 1.763(2) ?
C2 C3 . 1.382(3) ?
C3 C4 . 1.381(4) ?
C4 C5 . 1.374(4) ?
C5 C6 . 1.380(3) ?
C7 C8 . 1.384(3) ?
C7 C12 . 1.389(3) ?
C7 S1 . 1.771(2) ?
C8 C9 . 1.381(3) ?
C9 C10 . 1.376(4) ?
C10 C11 . 1.377(4) ?
C11 C12 . 1.381(4) ?
C16 C19 . 1.498(3) ?
C16 C17 . 1.534(3) ?
C16 C29 . 1.550(3) ?
C17 C18 . 1.343(3) ?
C17 C28 . 1.508(3) ?
C18 C21 . 1.517(3) ?
C19 C20 . 1.311(4) ?
C25 O7 . 1.462(4) ?
C25 C26 . 1.475(5) ?
C25 C30 . 1.496(6) ?
C25 C33 . 1.570(7) ?
C26 O8 . 1.469(3) ?
C26 C31 . 1.479(6) ?
C26 C32 . 1.632(7) ?
C27 C29 . 1.537(3) ?
C27 C28 . 1.540(3) ?
C27 S2 . 1.839(2) ?
C27 S1 . 1.856(2) ?
O1 S2 . 1.4350(16) ?
O2 S2 . 1.4373(17) ?
O3 S1 . 1.4368(16) ?
O4 S1 . 1.4345(15) ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
O8 B1 O7 . . 112.2(2) ?
O8 B1 C18 . . 127.0(2) ?
O7 B1 C18 . . 120.7(2) ?
C2 C1 C6 . . 120.6(2) ?
C2 C1 S2 . . 119.57(17) ?
C6 C1 S2 . . 119.38(17) ?
C3 C2 C1 . . 119.5(2) ?
C4 C3 C2 . . 119.7(2) ?
C5 C4 C3 . . 120.8(2) ?
C4 C5 C6 . . 120.2(2) ?
C5 C6 C1 . . 119.1(2) ?
C8 C7 C12 . . 121.0(2) ?
C8 C7 S1 . . 121.09(18) ?
C12 C7 S1 . . 117.88(19) ?
C9 C8 C7 . . 118.8(2) ?
C10 C9 C8 . . 120.9(3) ?
C11 C10 C9 . . 119.8(3) ?
C10 C11 C12 . . 120.7(3) ?
C11 C12 C7 . . 118.9(3) ?
C19 C16 C17 . . 113.25(18) ?
C19 C16 C29 . . 111.11(18) ?
C17 C16 C29 . . 104.38(16) ?
C18 C17 C28 . . 124.5(2) ?
C18 C17 C16 . . 127.23(19) ?
C28 C17 C16 . . 108.30(17) ?
C17 C18 C21 . . 121.6(2) ?
C17 C18 B1 . . 123.9(2) ?
C21 C18 B1 . . 114.4(2) ?
C20 C19 C16 . . 125.5(3) ?
O7 C25 C26 . . 103.7(3) ?
O7 C25 C30 . . 108.1(4) ?
C26 C25 C30 . . 120.7(4) ?
O7 C25 C33 . . 106.3(3) ?
C26 C25 C33 . . 108.1(4) ?
C30 C25 C33 . . 109.0(4) ?
O8 C26 C25 . . 103.9(2) ?
O8 C26 C31 . . 108.7(3) ?
C25 C26 C31 . . 122.4(4) ?
O8 C26 C32 . . 105.3(3) ?
C25 C26 C32 . . 107.6(4) ?
C31 C26 C32 . . 107.6(4) ?
C29 C27 C28 . . 102.53(16) ?
C29 C27 S2 . . 114.31(14) ?
C28 C27 S2 . . 106.64(13) ?
C29 C27 S1 . . 108.76(14) ?
C28 C27 S1 . . 112.73(15) ?
S2 C27 S1 . . 111.59(11) ?
C17 C28 C27 . . 103.76(16) ?
C27 C29 C16 . . 105.94(16) ?
B1 O7 C25 . . 107.8(2) ?
B1 O8 C26 . . 107.5(2) ?
O4 S1 O3 . . 118.50(10) ?
O4 S1 C7 . . 107.10(10) ?
O3 S1 C7 . . 109.73(11) ?
O4 S1 C27 . . 105.74(9) ?
O3 S1 C27 . . 108.02(9) ?
C7 S1 C27 . . 107.19(10) ?
O1 S2 O2 . . 118.61(11) ?
O1 S2 C1 . . 108.80(10) ?
O2 S2 C1 . . 106.60(10) ?
O1 S2 C27 . . 107.37(9) ?
O2 S2 C27 . . 105.01(10) ?
C1 S2 C27 . . 110.30(9) ?

_database_code_depnum_ccdc_archive 'CCDC 1005656'
#######################################################################
#
#                 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_I
_chemical_name_systematic        ?
_chemical_name_common            ALICI-20-A-PM-2
_chemical_formula_moiety         ?
_chemical_formula_sum            'C22 H23 N2 O2 S'
_chemical_formula_iupac          ?
_chemical_formula_weight         379.48

_chemical_melting_point          ?

_space_group_crystal_system      orthorhombic
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
'-x+1/2, -y, z+1/2'
'-x, -y, -z'
'-x-1/2, y-1/2, z'
'x, -y-1/2, z-1/2'
'x-1/2, y, -z-1/2'

_cell_length_a                   12.1138(10)
_cell_length_b                   15.4374(14)
_cell_length_c                   22.576(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     4221.8(7)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    9885
_cell_measurement_theta_min      2.6388
_cell_measurement_theta_max      23.2940
_cell_measurement_temperature    296.(2)

_exptl_crystal_description       prismatic
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.360
_exptl_crystal_size_mid          0.270
_exptl_crystal_size_min          0.160
_exptl_crystal_density_diffrn    1.194
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1608

_exptl_absorpt_coefficient_mu    0.171
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_correction_T_min  0.85
_exptl_absorpt_correction_T_max  0.97

_exptl_special_details           
;
;

_diffrn_ambient_temperature      296.(2)

_diffrn_source                   ?
_diffrn_source_type              ?

_diffrn_radiation_type           ?
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  ?

_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?

_diffrn_detector_area_resol_mean 8.3333

_diffrn_reflns_number            40940
_diffrn_reflns_av_R_equivalents  0.0349
_diffrn_reflns_av_sigmaI/netI    0.0192
_diffrn_reflns_theta_min         1.80
_diffrn_reflns_theta_max         25.39
_diffrn_reflns_theta_full        25.39
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_limit_l_max       27

_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.
;

_reflns_number_total             3871
_reflns_number_gt                2891
_reflns_threshold_expression     >2sigma(I)

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0678
_refine_ls_R_factor_gt           0.0463
_refine_ls_wR_factor_gt          0.1445
_refine_ls_wR_factor_ref         0.1733
_refine_ls_goodness_of_fit_ref   1.011
_refine_ls_restrained_S_all      1.011
_refine_ls_number_reflns         3871
_refine_ls_number_parameters     256
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment    refxyz
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.1142P)²+0.8202P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap

_refine_ls_shift/su_max          0.025
_refine_ls_shift/su_mean         0.001
_refine_diff_density_max         0.254
_refine_diff_density_min         -0.237
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

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'

_computing_data_collection       'Bruker Instrument Service v2010.9.0.0'
_computing_cell_refinement       'SAINT V7.68A (Bruker AXS, 2009)'
_computing_data_reduction        'SAINT V7.68A (Bruker AXS, 2009)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C C1 0.66423(18) 0.79852(13) 0.00611(10) 0.0545(5) Uani d . 1.0 . .
C C2 0.5742(2) 0.81397(16) -0.02965(12) 0.0695(7) Uani d . 1.0 . .
H H2 0.5219 0.7709 -0.0358 0.083 Uiso calc R 1.0 . .
C C3 0.5624(2) 0.89341(18) -0.05610(13) 0.0816(8) Uani d . 1.0 . .
H H3 0.5019 0.9032 -0.0805 0.098 Uiso calc R 1.0 . .
C C4 0.6381(2) 0.95934(17) -0.04752(11) 0.0731(7) Uani d . 1.0 . .
C C5 0.7277(2) 0.94313(15) -0.01116(11) 0.0699(7) Uani d . 1.0 . .
H H5 0.7795 0.9866 -0.0047 0.084 Uiso calc R 1.0 . .
C C6 0.74171(18) 0.86374(15) 0.01562(10) 0.0615(6) Uani d . 1.0 . .
H H6 0.8024 0.8537 0.0399 0.074 Uiso calc R 1.0 . .
C C8 0.5169(3) 0.45881(18) 0.22446(12) 0.0814(8) Uani d . 1.0 . .
H H8 0.5364 0.4358 0.2611 0.098 Uiso calc R 1.0 . .
C C9 0.4994(2) 0.54645(17) 0.21884(11) 0.0754(7) Uani d . 1.0 . .
H H9 0.5078 0.5822 0.2517 0.091 Uiso calc R 1.0 . .
C C10 0.46967(17) 0.58187(15) 0.16541(10) 0.0600(6) Uani d . 1.0 . .
C C11 0.4611(2) 0.52787(17) 0.11690(12) 0.0754(7) Uani d . 1.0 . .
H H11 0.4433 0.5514 0.0802 0.09 Uiso calc R 1.0 . .
C C12 0.4785(2) 0.43944(16) 0.12162(12) 0.0746(7) Uani d . 1.0 . .
H H12 0.4718 0.4039 0.0886 0.09 Uiso calc R 1.0 . .
C C13 0.50583(18) 0.40474(15) 0.17602(11) 0.0620(6) Uani d . 1.0 . .
C C14 0.68707(19) 0.73847(15) 0.15611(11) 0.0633(6) Uani d . 1.0 . .
H H14A 0.658 0.7156 0.193 0.076 Uiso calc R 1.0 . .
H H14B 0.7625 0.7182 0.1523 0.076 Uiso calc R 1.0 . .
C C15 0.50290(18) 0.72178(14) 0.10818(11) 0.0619(6) Uani d . 1.0 . .
H H15A 0.4693 0.7017 0.0717 0.074 Uiso calc R 1.0 . .
H H15B 0.4921 0.7839 0.1106 0.074 Uiso calc R 1.0 . .
C C16 0.44577(19) 0.67826(16) 0.16071(12) 0.0672(6) Uani d . 1.0 B .
H H16 0.4723 0.7061 0.197 0.081 Uiso calc R 1.0 . .
C C17 0.5231(2) 0.31267(18) 0.18137(12) 0.0716(7) Uani d . 1.0 . .
C C18 0.6244(4) 1.0462(2) -0.07739(16) 0.1123(11) Uani d . 1.0 . .
H H18A 0.6522 1.091 -0.0519 0.168 Uiso calc R 1.0 . .
H H18B 0.5476 1.0563 -0.0852 0.168 Uiso calc R 1.0 . .
H H18C 0.6647 1.0465 -0.114 0.168 Uiso calc R 1.0 . .
C C19 0.6939(2) 0.90984(16) 0.16048(11) 0.0667(6) Uani d . 1.0 . .
C C20 0.7045(3) 1.00452(17) 0.15831(16) 0.0943(9) Uani d . 1.0 . .
H H20A 0.7569 1.0203 0.1283 0.141 Uiso calc R 1.0 . .
H H20B 0.7295 1.0255 0.196 0.141 Uiso calc R 1.0 . .
H H20C 0.6341 1.0298 0.1492 0.141 Uiso calc R 1.0 . .
C C21 0.68823(18) 0.83336(16) 0.15981(10) 0.0619(6) Uani d . 1.0 . .
C C22 0.3232(2) 0.6957(2) 0.15550(17) 0.0952(10) Uani d . 1.0 . .
H H22A 0.2843 0.6622 0.1283 0.696(9) Uiso calc R 1.0 A 1
H H22B 0.3012 0.744 0.134 0.304 Uiso calc R 1.0 A 2
N N1 0.5355(2) 0.23918(16) 0.18559(12) 0.0885(7) Uani d . 1.0 . .
N N4 0.62191(14) 0.70290(10) 0.10679(8) 0.0547(5) Uani d . 1.0 . .
O O1 0.79379(14) 0.68187(12) 0.05076(9) 0.0827(6) Uani d . 1.0 . .
O O2 0.61498(17) 0.63625(10) 0.00823(8) 0.0792(5) Uani d . 1.0 . .
S S1 0.67919(5) 0.69731(3) 0.04123(3) 0.0600(2) Uani d . 1.0 . .
C C23A 0.2685(4) 0.7511(5) 0.1843(3) 0.114(2) Uani d P 0.696(9) B 1
H H23A 0.207 0.734 0.206 0.136 Uiso calc PR 0.696(9) B 1
H H23B 0.2897 0.809 0.1839 0.136 Uiso calc PR 0.696(9) B 1
C C23B 0.2507(13) 0.6504(16) 0.1777(8) 0.160(10) Uani d P 0.304(9) B 2
H H23C 0.1973 0.6754 0.2019 0.192 Uiso calc PR 0.304(9) B 2
H H23D 0.2492 0.5911 0.1703 0.192 Uiso calc PR 0.304(9) B 2


_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_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
C1 C2 . 1.377(3) ?
C1 C6 . 1.393(3) ?
C1 S1 . 1.762(2) ?
C2 C3 . 1.371(4) ?
C2 H2 . 0.93 ?
C3 C4 . 1.383(4) ?
C3 H3 . 0.93 ?
C4 C5 . 1.384(4) ?
C4 C18 . 1.510(4) ?
C5 C6 . 1.377(3) ?
C5 H5 . 0.93 ?
C6 H6 . 0.93 ?
C8 C9 . 1.375(4) ?
C8 C13 . 1.382(4) ?
C8 H8 . 0.93 ?
C9 C10 . 1.372(3) ?
C9 H9 . 0.93 ?
C10 C11 . 1.380(3) ?
C10 C16 . 1.520(3) ?
C11 C12 . 1.385(3) ?
C11 H11 . 0.93 ?
C12 C13 . 1.380(3) ?
C12 H12 . 0.93 ?
C13 C17 . 1.442(3) ?
C14 C21 . 1.467(3) ?
C14 N4 . 1.471(3) ?
C14 H14A . 0.97 ?
C14 H14B . 0.97 ?
C15 N4 . 1.471(3) ?
C15 C16 . 1.529(3) ?
C15 H15A . 0.97 ?
C15 H15B . 0.97 ?
C16 C22 . 1.513(4) ?
C16 H16 . 0.98 ?
C17 N1 . 1.148(3) ?
C18 H18A . 0.96 ?
C18 H18B . 0.96 ?
C18 H18C . 0.96 ?
C19 C21 . 1.183(3) ?
C19 C20 . 1.468(3) ?
C20 H20A . 0.96 ?
C20 H20B . 0.96 ?
C20 H20C . 0.96 ?
C22 C23B . 1.23(2) ?
C22 C23A . 1.263(6) ?
C22 H22A . 0.93 ?
C22 H22B . 0.93 ?
N4 S1 . 1.637(2) ?
O1 S1 . 1.4249(18) ?
O2 S1 . 1.4313(18) ?
C23A H23A . 0.93 ?
C23A H23B . 0.93 ?
C23B H23C . 0.93 ?
C23B H23D . 0.93 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C2 C1 C6 . . 119.9(2) ?
C2 C1 S1 . . 119.92(17) ?
C6 C1 S1 . . 120.15(18) ?
C3 C2 C1 . . 119.5(2) ?
C3 C2 H2 . . 120.2 ?
C1 C2 H2 . . 120.2 ?
C2 C3 C4 . . 121.9(2) ?
C2 C3 H3 . . 119.1 ?
C4 C3 H3 . . 119.1 ?
C5 C4 C3 . . 118.0(2) ?
C5 C4 C18 . . 120.8(3) ?
C3 C4 C18 . . 121.2(3) ?
C6 C5 C4 . . 121.2(2) ?
C6 C5 H5 . . 119.4 ?
C4 C5 H5 . . 119.4 ?
C5 C6 C1 . . 119.5(2) ?
C5 C6 H6 . . 120.2 ?
C1 C6 H6 . . 120.2 ?
C9 C8 C13 . . 120.4(2) ?
C9 C8 H8 . . 119.8 ?
C13 C8 H8 . . 119.8 ?
C10 C9 C8 . . 120.9(2) ?
C10 C9 H9 . . 119.6 ?
C8 C9 H9 . . 119.6 ?
C9 C10 C11 . . 118.5(2) ?
C9 C10 C16 . . 120.1(2) ?
C11 C10 C16 . . 121.4(2) ?
C10 C11 C12 . . 121.5(2) ?
C10 C11 H11 . . 119.2 ?
C12 C11 H11 . . 119.2 ?
C13 C12 C11 . . 119.2(2) ?
C13 C12 H12 . . 120.4 ?
C11 C12 H12 . . 120.4 ?
C12 C13 C8 . . 119.5(2) ?
C12 C13 C17 . . 119.5(2) ?
C8 C13 C17 . . 121.0(2) ?
C21 C14 N4 . . 114.88(18) ?
C21 C14 H14A . . 108.5 ?
N4 C14 H14A . . 108.5 ?
C21 C14 H14B . . 108.5 ?
N4 C14 H14B . . 108.5 ?
H14A C14 H14B . . 107.5 ?
N4 C15 C16 . . 111.91(18) ?
N4 C15 H15A . . 109.2 ?
C16 C15 H15A . . 109.2 ?
N4 C15 H15B . . 109.2 ?
C16 C15 H15B . . 109.2 ?
H15A C15 H15B . . 107.9 ?
C22 C16 C10 . . 111.5(2) ?
C22 C16 C15 . . 107.8(2) ?
C10 C16 C15 . . 113.47(19) ?
C22 C16 H16 . . 108.0 ?
C10 C16 H16 . . 108.0 ?
C15 C16 H16 . . 108.0 ?
N1 C17 C13 . . 179.1(3) ?
C4 C18 H18A . . 109.5 ?
C4 C18 H18B . . 109.5 ?
H18A C18 H18B . . 109.5 ?
C4 C18 H18C . . 109.5 ?
H18A C18 H18C . . 109.5 ?
H18B C18 H18C . . 109.5 ?
C21 C19 C20 . . 176.9(3) ?
C19 C20 H20A . . 109.5 ?
C19 C20 H20B . . 109.5 ?
H20A C20 H20B . . 109.5 ?
C19 C20 H20C . . 109.5 ?
H20A C20 H20C . . 109.5 ?
H20B C20 H20C . . 109.5 ?
C19 C21 C14 . . 176.2(3) ?
C23B C22 C23A . . 78.4(10) ?
C23B C22 C16 . . 124.6(7) ?
C23A C22 C16 . . 126.6(4) ?
C23B C22 H22A . . 65.8 ?
C23A C22 H22A . . 116.7 ?
C16 C22 H22A . . 116.7 ?
C23B C22 H22B . . 117.7 ?
C23A C22 H22B . . 64.8 ?
C16 C22 H22B . . 117.7 ?
H22A C22 H22B . . 87.5 ?
C14 N4 C15 . . 115.83(18) ?
C14 N4 S1 . . 118.46(15) ?
C15 N4 S1 . . 116.43(15) ?
O1 S1 O2 . . 119.86(12) ?
O1 S1 N4 . . 106.58(11) ?
O2 S1 N4 . . 105.96(11) ?
O1 S1 C1 . . 108.46(11) ?
O2 S1 C1 . . 107.09(11) ?
N4 S1 C1 . . 108.46(9) ?
C22 C23A H23A . . 120.0 ?
C22 C23A H23B . . 120.0 ?
H23A C23A H23B . . 120.0 ?
C22 C23B H23C . . 120.0 ?
C22 C23B H23D . . 120.0 ?
H23C C23B H23D . . 120.0 ?

_database_code_depnum_ccdc_archive 'CCDC 1005657'
