# Electronic Supplementary Material (ESI) for RSC Advances.
# 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_sci216_cr720a_0m

_audit_creation_date             2014-01-03T23:53:55-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C19 H24 Cl2 O3'
_chemical_formula_sum            'C19 H24 Cl2 O3'
_chemical_formula_weight         371.28

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, -y, -z'
_space_group_crystal_system      triclinic
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
_space_group_IT_number           2
_cell_length_a                   9.5268(4)
_cell_length_b                   11.1801(6)
_cell_length_c                   11.2526(5)
_cell_angle_alpha                61.212(2)
_cell_angle_beta                 66.057(2)
_cell_angle_gamma                71.403(3)
_cell_volume                     948.53(8)
_cell_formula_units_Z            2
_cell_measurement_temperature    298
_cell_measurement_reflns_used    4758
_cell_measurement_theta_min      2.168
_cell_measurement_theta_max      24.485

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_exptl_crystal_density_diffrn    1.3
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             392
_exptl_special_details           
;
 ?
;

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    0.356
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
        SADABS-2008/1 (Bruker,2008) was used for absorption correction.
        R(int) was 0.0472 before and 0.0388 after correction.
        The Ratio of minimum to maximum transmission is 0.9173.
        The λ/2 correction factor is 0.0015.
;
_exptl_absorpt_correction_T_min  0.684
_exptl_absorpt_correction_T_max  0.7457

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_source                   'fine-focus sealed tube'
_diffrn_ambient_temperature      298
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           'MO K\a'
_diffrn_radiation_monochromator  graphite
_diffrn_reflns_av_R_equivalents  0.0233
_diffrn_reflns_number            11741
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         2.1
_diffrn_reflns_theta_max         25.02
_diffrn_reflns_theta_full        25.02
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_reflns_number_total             3336
_reflns_number_gt                2371
_reflns_threshold_expression     >2sigma(I)

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_reduction        'SAINT v7.68A (Bruker, 2009)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  
;
        SHELXL, G.M. Sheldrick, Acta Cryst.
        2008). A64, 112-122
;
_computing_molecular_graphics    
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
        J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material  
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
        J. Appl. Cryst. (2009). 42, 339-341.
;

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION
#----------------------------------------------------------------------------#

_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_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)+(0.0460P)²+0.3658P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_number_reflns         3336
_refine_ls_number_parameters     220
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0697
_refine_ls_R_factor_gt           0.0439
_refine_ls_wR_factor_ref         0.1171
_refine_ls_wR_factor_gt          0.1022
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_restrained_S_all      1.047
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.327
_refine_diff_density_min         -0.431
_refine_diff_density_rms         0.039

#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

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 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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
Cl1 Cl 1.07826(11) 0.30434(9) 0.11167(8) 0.0909(3) Uani 1 1 d . . .
Cl2 Cl 1.18089(8) 0.24421(10) 0.56964(8) 0.0831(3) Uani 1 1 d . . .
O1 O 0.52195(18) 0.32961(16) 0.73355(19) 0.0589(5) Uani 1 1 d . . .
O2 O 0.73850(17) 0.01187(15) 1.04751(17) 0.0523(4) Uani 1 1 d . . .
H2 H 0.6577 -0.013 1.0644 0.078 Uiso 1 1 calc R . .
O3 O 0.55376(19) 0.10032(17) 0.83257(19) 0.0597(5) Uani 1 1 d . . .
C1 C 1.0214(3) 0.2463(3) 0.2957(3) 0.0554(6) Uani 1 1 d . . .
C2 C 1.1090(3) 0.2640(3) 0.3558(3) 0.0556(6) Uani 1 1 d . . .
H2A H 1.1979 0.3053 0.2991 0.067 Uiso 1 1 calc R . .
C3 C 1.0630(3) 0.2196(3) 0.5014(3) 0.0504(6) Uani 1 1 d . . .
C4 C 0.9305(2) 0.1578(2) 0.5915(2) 0.0458(6) Uani 1 1 d . . .
C5 C 0.8795(3) 0.1086(2) 0.7507(2) 0.0509(6) Uani 1 1 d . . .
H5A H 0.9689 0.093 0.78 0.061 Uiso 1 1 calc R . .
H5B H 0.8436 0.0206 0.7937 0.061 Uiso 1 1 calc R . .
C6 C 0.7484(2) 0.2094(2) 0.8095(2) 0.0407(5) Uani 1 1 d . . .
C7 C 0.6004(3) 0.2061(2) 0.7926(2) 0.0443(5) Uani 1 1 d . . .
C8 C 0.3748(3) 0.3305(3) 0.7219(4) 0.0784(9) Uani 1 1 d . . .
H8A H 0.3098 0.2758 0.814 0.094 Uiso 1 1 calc R . .
H8B H 0.3931 0.2913 0.6556 0.094 Uiso 1 1 calc R . .
C9 C 0.2979(4) 0.4738(3) 0.6714(4) 0.1030(12) Uani 1 1 d . . .
H9A H 0.2718 0.509 0.7418 0.154 Uiso 1 1 calc R . .
H9B H 0.2048 0.4778 0.655 0.154 Uiso 1 1 calc R . .
H9C H 0.3665 0.5287 0.5842 0.154 Uiso 1 1 calc R . .
C10 C 0.7944(3) 0.3531(2) 0.7467(2) 0.0493(6) Uani 1 1 d . . .
H10A H 0.8663 0.3743 0.6512 0.059 Uiso 1 1 calc R . .
H10B H 0.7032 0.4238 0.7428 0.059 Uiso 1 1 calc R . .
C11 C 0.8719(3) 0.3463(3) 0.8468(3) 0.0641(7) Uani 1 1 d . . .
H11A H 0.98 0.3583 0.7968 0.077 Uiso 1 1 calc R . .
H11B H 0.8192 0.4185 0.8814 0.077 Uiso 1 1 calc R . .
C12 C 0.8596(3) 0.2050(2) 0.9698(3) 0.0530(6) Uani 1 1 d . . .
H12A H 0.8393 0.2112 1.0585 0.064 Uiso 1 1 calc R . .
H12B H 0.955 0.1414 0.9541 0.064 Uiso 1 1 calc R . .
C13 C 0.7247(2) 0.1574(2) 0.9735(2) 0.0419(5) Uani 1 1 d . . .
C14 C 0.5655(2) 0.2283(2) 1.0426(2) 0.0470(6) Uani 1 1 d . . .
H14A H 0.5498 0.3241 0.977 0.056 Uiso 1 1 calc R . .
H14B H 0.4846 0.1846 1.0549 0.056 Uiso 1 1 calc R . .
C15 C 0.5455(3) 0.2246(3) 1.1836(3) 0.0519(6) Uani 1 1 d . . .
C16 C 0.5304(4) 0.0911(3) 1.3085(3) 0.0958(11) Uani 1 1 d . . .
H16A H 0.5074 0.1051 1.3927 0.144 Uiso 1 1 calc R . .
H16B H 0.6261 0.0287 1.2966 0.144 Uiso 1 1 calc R . .
H16C H 0.4479 0.0528 1.3174 0.144 Uiso 1 1 calc R . .
C17 C 0.5392(3) 0.3379(3) 1.1961(3) 0.0735(8) Uani 1 1 d . . .
H17A H 0.525 0.3342 1.2845 0.088 Uiso 1 1 calc R . .
H17B H 0.5489 0.4214 1.1165 0.088 Uiso 1 1 calc R . .
C18 C 0.8480(3) 0.1409(2) 0.5243(3) 0.0547(6) Uani 1 1 d . . .
H18 H 0.7597 0.0986 0.5802 0.066 Uiso 1 1 calc R . .
C19 C 0.8910(3) 0.1839(3) 0.3791(3) 0.0587(7) Uani 1 1 d . . .
H19 H 0.8328 0.1709 0.3381 0.07 Uiso 1 1 calc R . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_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
Cl1 C1 1.739(3) . ?
Cl2 C3 1.739(2) . ?
O1 C7 1.329(3) . ?
O1 C8 1.456(3) . ?
O2 H2 0.82 . ?
O2 C13 1.416(2) . ?
O3 C7 1.208(3) . ?
C1 C2 1.373(3) . ?
C1 C19 1.373(3) . ?
C2 H2A 0.93 . ?
C2 C3 1.377(3) . ?
C3 C4 1.393(3) . ?
C4 C5 1.505(3) . ?
C4 C18 1.392(3) . ?
C5 H5A 0.97 . ?
C5 H5B 0.97 . ?
C5 C6 1.555(3) . ?
C6 C7 1.512(3) . ?
C6 C10 1.541(3) . ?
C6 C13 1.583(3) . ?
C8 H8A 0.97 . ?
C8 H8B 0.97 . ?
C8 C9 1.463(4) . ?
C9 H9A 0.96 . ?
C9 H9B 0.96 . ?
C9 H9C 0.96 . ?
C10 H10A 0.97 . ?
C10 H10B 0.97 . ?
C10 C11 1.541(3) . ?
C11 H11A 0.97 . ?
C11 H11B 0.97 . ?
C11 C12 1.519(3) . ?
C12 H12A 0.97 . ?
C12 H12B 0.97 . ?
C12 C13 1.519(3) . ?
C13 C14 1.550(3) . ?
C14 H14A 0.97 . ?
C14 H14B 0.97 . ?
C14 C15 1.500(3) . ?
C15 C16 1.475(4) . ?
C15 C17 1.320(4) . ?
C16 H16A 0.96 . ?
C16 H16B 0.96 . ?
C16 H16C 0.96 . ?
C17 H17A 0.93 . ?
C17 H17B 0.93 . ?
C18 H18 0.93 . ?
C18 C19 1.377(3) . ?
C19 H19 0.93 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C7 O1 C8 116.23(19) . . ?
C13 O2 H2 109.5 . . ?
C2 C1 Cl1 118.9(2) . . ?
C2 C1 C19 120.8(2) . . ?
C19 C1 Cl1 120.3(2) . . ?
C1 C2 H2A 120.5 . . ?
C1 C2 C3 118.9(2) . . ?
C3 C2 H2A 120.5 . . ?
C2 C3 Cl2 116.19(18) . . ?
C2 C3 C4 123.0(2) . . ?
C4 C3 Cl2 120.80(19) . . ?
C3 C4 C5 123.4(2) . . ?
C18 C4 C3 115.3(2) . . ?
C18 C4 C5 121.2(2) . . ?
C4 C5 H5A 108.6 . . ?
C4 C5 H5B 108.6 . . ?
C4 C5 C6 114.64(18) . . ?
H5A C5 H5B 107.6 . . ?
C6 C5 H5A 108.6 . . ?
C6 C5 H5B 108.6 . . ?
C5 C6 C13 109.41(17) . . ?
C7 C6 C5 107.38(18) . . ?
C7 C6 C10 116.36(18) . . ?
C7 C6 C13 108.65(16) . . ?
C10 C6 C5 112.54(17) . . ?
C10 C6 C13 102.23(17) . . ?
O1 C7 C6 114.69(19) . . ?
O3 C7 O1 122.1(2) . . ?
O3 C7 C6 123.2(2) . . ?
O1 C8 H8A 110.1 . . ?
O1 C8 H8B 110.1 . . ?
O1 C8 C9 108.0(2) . . ?
H8A C8 H8B 108.4 . . ?
C9 C8 H8A 110.1 . . ?
C9 C8 H8B 110.1 . . ?
C8 C9 H9A 109.5 . . ?
C8 C9 H9B 109.5 . . ?
C8 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C6 C10 H10A 110.5 . . ?
C6 C10 H10B 110.5 . . ?
H10A C10 H10B 108.7 . . ?
C11 C10 C6 106.07(19) . . ?
C11 C10 H10A 110.5 . . ?
C11 C10 H10B 110.5 . . ?
C10 C11 H11A 110.4 . . ?
C10 C11 H11B 110.4 . . ?
H11A C11 H11B 108.6 . . ?
C12 C11 C10 106.85(19) . . ?
C12 C11 H11A 110.4 . . ?
C12 C11 H11B 110.4 . . ?
C11 C12 H12A 110.7 . . ?
C11 C12 H12B 110.7 . . ?
C11 C12 C13 105.20(19) . . ?
H12A C12 H12B 108.8 . . ?
C13 C12 H12A 110.7 . . ?
C13 C12 H12B 110.7 . . ?
O2 C13 C6 113.38(17) . . ?
O2 C13 C12 108.92(18) . . ?
O2 C13 C14 110.93(17) . . ?
C12 C13 C6 101.91(17) . . ?
C12 C13 C14 111.87(18) . . ?
C14 C13 C6 109.55(17) . . ?
C13 C14 H14A 108.3 . . ?
C13 C14 H14B 108.3 . . ?
H14A C14 H14B 107.4 . . ?
C15 C14 C13 115.91(19) . . ?
C15 C14 H14A 108.3 . . ?
C15 C14 H14B 108.3 . . ?
C16 C15 C14 118.1(2) . . ?
C17 C15 C14 121.0(2) . . ?
C17 C15 C16 120.9(3) . . ?
C15 C16 H16A 109.5 . . ?
C15 C16 H16B 109.5 . . ?
C15 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C15 C17 H17A 120 . . ?
C15 C17 H17B 120 . . ?
H17A C17 H17B 120 . . ?
C4 C18 H18 118.5 . . ?
C19 C18 C4 123.1(2) . . ?
C19 C18 H18 118.5 . . ?
C1 C19 C18 118.9(2) . . ?
C1 C19 H19 120.6 . . ?
C18 C19 H19 120.6 . . ?

# The following lines are used to test the character set of files sent by
# network email or other means. They are not part of the CIF data set
# abcdefghijklmnopqrstuvwxyzABCDEFGHIJKLMNOPQRSTUVWXYZ0123456789
# !@#$%^&*()_+{}:"~<>?|\-=[];'`,./

# END of CIF
_database_code_depnum_ccdc_archive 'CCDC 1001586'
#######################################################################
#
#                 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_rd

_audit_creation_date             2014-05-07T15:37:54-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_formula_moiety         'C16 H25 N O3 S'
_chemical_formula_sum            'C16 H25 N O3 S'
_chemical_formula_weight         311.45
_chemical_absolute_configuration unk

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_space_group_crystal_system      orthorhombic
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
_space_group_IT_number           19
_symmetry_Int_Tables_number      19
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 x+1/2,-y+1/2,-z
3 -x,y+1/2,-z+1/2
4 -x+1/2,-y,z+1/2
_cell_length_a                   7.0300(14)
_cell_length_b                   14.160(3)
_cell_length_c                   17.880(4)
_cell_angle_alpha                90
_cell_angle_beta                 90.00(3)
_cell_angle_gamma                90
_cell_volume                     1779.9(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    298
_cell_measurement_reflns_used    3641
_cell_measurement_theta_min      3.1
_cell_measurement_theta_max      27.5

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       block
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_exptl_crystal_density_diffrn    1.1622
_exptl_crystal_F_000             672.7988
_exptl_special_details           
;
 ?
;

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    0.191
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.927
_exptl_absorpt_correction_T_max  1

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_source                   'Sealed Tube'
_diffrn_ambient_temperature      298
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_monochromator  'Graphite Monochromator'
_diffrn_detector                 CCD
_diffrn_detector_area_resol_mean 13.6612
_diffrn_orient_matrix_type       d*Trek
_diffrn_orient_matrix_ub_11      0.071457
_diffrn_orient_matrix_ub_12      0.119429
_diffrn_orient_matrix_ub_13      -0.029125
_diffrn_orient_matrix_ub_21      0.056747
_diffrn_orient_matrix_ub_22      -0.038212
_diffrn_orient_matrix_ub_23      -0.017463
_diffrn_orient_matrix_ub_31      -0.01781
_diffrn_orient_matrix_ub_32      -0.002255
_diffrn_orient_matrix_ub_33      -0.052942
_diffrn_measurement_device       
;
        XtaLABmini: Fixed Chi 2 circle
;
_diffrn_measurement_device_type  'Rigaku Mercury375R (2x2 bin mode)'
_diffrn_measurement_method       'ω scans'
_diffrn_standards_number         0
_diffrn_reflns_av_R_equivalents  0.048
_diffrn_reflns_number            18421
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         3.09
_diffrn_reflns_theta_max         27.51
_diffrn_reflns_theta_full        26
_diffrn_measured_fraction_theta_full 0.9969
_diffrn_measured_fraction_theta_max 0.9936
_reflns_number_total             4056
_reflns_number_gt                3236
_reflns_threshold_expression     I>=2u(I)

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       
;
        CrystalClear-SM Expert 2.0 r15 (Rigaku, 2011)
;
_computing_cell_refinement       
;
        CrystalClear-SM Expert 2.0 r15 (Rigaku, 2011)
;
_computing_data_reduction        
;
        CrystalClear-SM Expert 2.0 r15 (Rigaku, 2011)
;
_computing_structure_solution    
;
olex2.solve (L.J. Bourhis, O.V. Dolomanov, R.J. Gildea, J.A.K. Howard,
        H. Puschmann, in preparation, 2011)
;
_computing_structure_refinement  
;
olex2.refine (L.J. Bourhis, O.V. Dolomanov, R.J. Gildea, J.A.K. Howard,
        H. Puschmann, in preparation, 2011)
;
_computing_molecular_graphics    
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
        J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material  
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
        J. Appl. Cryst. (2009). 42, 339-341.
;

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION
#----------------------------------------------------------------------------#

_atom_sites_solution_primary     iterative

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0478P)²+0.3089P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    mixed
_refine_ls_number_reflns         4056
_refine_ls_number_parameters     205
_refine_ls_number_restraints     0
_refine_ls_number_constraints    34
_refine_ls_R_factor_all          0.0623
_refine_ls_R_factor_gt           0.0475
_refine_ls_wR_factor_ref         0.1109
_refine_ls_wR_factor_gt          0.1023
_refine_ls_goodness_of_fit_ref   1.0305
_refine_ls_restrained_S_all      1.0305
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_ls_abs_structure_details 
'Flack, H. D. (1983). Acta Cryst. A39, 876-881.'
_refine_ls_abs_structure_Flack   0.03(10)
_refine_diff_density_max         0.2045
_refine_diff_density_min         -0.1659
_refine_diff_density_rms         0.0446

#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
H 0 0 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
C 0.00347 0.00161 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
S 0.12424 0.12443 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
O 0.01158 0.00611 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
N 0.00653 0.00323 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'

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
S S 0.18221(8) 0.59277(4) 0.31424(3) 0.05148(16) Uani 1
O2 O 0.5051(2) 0.83497(12) 0.06416(9) 0.0588(4) Uani 1
O3 O 0.7498(2) 0.79962(12) 0.16625(10) 0.0584(4) Uani 1
N1 N 0.3678(3) 0.51949(14) 0.30993(11) 0.0501(5) Uani 1
O1 O 0.0103(3) 0.54848(16) 0.28184(11) 0.0764(6) Uani 1
C3 C 0.6649(5) 0.4021(2) 0.15996(17) 0.0763(8) Uani 1
C7 C 0.5975(3) 0.65073(15) 0.19955(12) 0.0461(5) Uani 1
C8 C 0.4778(3) 0.75194(16) 0.10191(12) 0.0460(5) Uani 1
C9 C 0.4487(3) 0.58699(15) 0.18646(12) 0.0451(5) Uani 1
C10 C 0.3345(4) 0.68855(18) 0.08833(13) 0.0540(6) Uani 1
C11 C 0.6119(3) 0.73238(15) 0.15818(12) 0.0442(5) Uani 1
C12 C 0.3213(3) 0.60647(17) 0.13081(13) 0.0537(6) Uani 1
C13 C 0.4274(3) 0.49744(16) 0.23189(13) 0.0505(5) Uani 1
C4 C 0.0915(5) 0.4918(2) 0.44142(17) 0.0873(10) Uani 1
C5 C 0.8198(6) 0.4223(3) 0.1260(2) 0.0960(11) Uani 1
C6 C 0.6066(4) 0.43694(18) 0.23497(15) 0.0592(7) Uani 1
C14 C 0.1463(4) 0.59035(19) 0.41595(14) 0.0662(7) Uani 1
C18 C 0.3694(4) 0.8570(2) 0.00734(19) 0.0872(10) Uani 1
C15 C -0.0215(6) 0.6580(3) 0.42734(19) 0.1126(15) Uani 1
C20 C 0.8971(4) 0.7829(2) 0.21958(17) 0.0766(8) Uani 1
C16 C 0.3241(6) 0.6262(3) 0.4535(2) 0.1213(15) Uani 1
H12 H 0.2236(3) 0.56393(17) 0.12113(13) 0.0644(7) Uiso 1
H10 H 0.2463(4) 0.70038(18) 0.05074(13) 0.0648(7) Uiso 1
H7 H 0.6872(3) 0.63777(15) 0.23640(12) 0.0553(6) Uiso 1
H1 H 0.350(4) 0.4698(18) 0.3365(14) 0.0602(6) Uiso 1
H3 H 0.5809(5) 0.3619(2) 0.13543(17) 0.0916(10) Uiso 1
H13 H 0.3266(3) 0.45952(16) 0.20884(13) 0.0607(7) Uiso 1
H4a H -0.007(2) 0.4677(7) 0.4096(9) 0.1309(15) Uiso 1
H4b H 0.2005(10) 0.4512(5) 0.4387(13) 0.1309(15) Uiso 1
H4c H 0.046(3) 0.4943(3) 0.4921(5) 0.1309(15) Uiso 1
H6a H 0.5842(4) 0.38334(18) 0.26758(15) 0.0711(8) Uiso 1
H6b H 0.7094(4) 0.47384(18) 0.25627(15) 0.0711(8) Uiso 1
H18a H 0.368(3) 0.8073(9) -0.0292(8) 0.1308(15) Uiso 1
H18b H 0.2455(8) 0.8630(18) 0.0294(3) 0.1308(15) Uiso 1
H18c H 0.404(2) 0.9154(10) -0.0163(10) 0.1308(15) Uiso 1
H15a H 0.0106(17) 0.7190(6) 0.4077(16) 0.169(2) Uiso 1
H15b H -0.1313(13) 0.6340(11) 0.4017(14) 0.169(2) Uiso 1
H15c H -0.049(3) 0.6634(17) 0.4798(2) 0.169(2) Uiso 1
H20a H 0.964(2) 0.7259(9) 0.2068(7) 0.1149(13) Uiso 1
H20b H 0.9846(19) 0.8349(8) 0.2193(9) 0.1149(13) Uiso 1
H20c H 0.8424(5) 0.7765(16) 0.2685(2) 0.1149(13) Uiso 1
H16a H 0.4223(17) 0.5793(10) 0.4500(17) 0.182(2) Uiso 1
H16b H 0.366(3) 0.6832(14) 0.4293(13) 0.182(2) Uiso 1
H16c H 0.2978(14) 0.639(2) 0.5052(5) 0.182(2) Uiso 1
H5a H 0.837(5) 0.398(2) 0.074(2) 0.117(12) Uiso 1
H5b H 0.917(7) 0.475(3) 0.149(2) 0.159(19) Uiso 1



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S N1 1.6686(19) . ?
S O1 1.480(2) . ?
S C14 1.836(3) . ?
O2 C8 1.369(3) . ?
O2 C18 1.428(3) . ?
O3 C11 1.366(3) . ?
O3 C20 1.428(3) . ?
N1 C13 1.490(3) . ?
N1 H1 0.86(3) . ?
C3 C5 1.279(5) . ?
C3 C6 1.487(4) . ?
C3 H3 0.93 . ?
C7 C9 1.401(3) . ?
C7 C11 1.376(3) . ?
C7 H7 0.93 . ?
C8 C10 1.371(3) . ?
C8 C11 1.406(3) . ?
C9 C12 1.367(3) . ?
C9 C13 1.513(3) . ?
C10 C12 1.392(3) . ?
C10 H10 0.93 . ?
C12 H12 0.93 . ?
C13 C6 1.524(3) . ?
C13 H13 0.98 . ?
C4 C14 1.517(4) . ?
C4 H4a 0.96 . ?
C4 H4b 0.96 . ?
C4 H4c 0.96 . ?
C5 H5a 1.01(4) . ?
C5 H5b 1.09(5) . ?
C6 H6a 0.97 . ?
C6 H6b 0.97 . ?
C14 C15 1.533(4) . ?
C14 C16 1.508(5) . ?
C18 H18a 0.96 . ?
C18 H18b 0.96 . ?
C18 H18c 0.96 . ?
C15 H15a 0.96 . ?
C15 H15b 0.96 . ?
C15 H15c 0.96 . ?
C20 H20a 0.96 . ?
C20 H20b 0.96 . ?
C20 H20c 0.96 . ?
C16 H16a 0.96 . ?
C16 H16b 0.96 . ?
C16 H16c 0.96 . ?

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 S N1 110.91(11) . . ?
C14 S N1 98.14(11) . . ?
C14 S O1 105.51(13) . . ?
C18 O2 C8 116.4(2) . . ?
C20 O3 C11 118.00(18) . . ?
C13 N1 S 113.18(15) . . ?
H1 N1 S 111.7(18) . . ?
H1 N1 C13 112.8(16) . . ?
C6 C3 C5 126.1(3) . . ?
H3 C3 C5 117.0(3) . . ?
H3 C3 C6 116.97(16) . . ?
C11 C7 C9 120.4(2) . . ?
H7 C7 C9 119.80(13) . . ?
H7 C7 C11 119.80(13) . . ?
C10 C8 O2 125.3(2) . . ?
C11 C8 O2 115.34(19) . . ?
C11 C8 C10 119.4(2) . . ?
C12 C9 C7 118.7(2) . . ?
C13 C9 C7 121.59(19) . . ?
C13 C9 C12 119.7(2) . . ?
C12 C10 C8 120.0(2) . . ?
H10 C10 C8 120.02(13) . . ?
H10 C10 C12 120.02(14) . . ?
C7 C11 O3 125.49(19) . . ?
C8 C11 O3 114.45(19) . . ?
C8 C11 C7 120.1(2) . . ?
C10 C12 C9 121.5(2) . . ?
H12 C12 C9 119.27(14) . . ?
H12 C12 C10 119.27(14) . . ?
C9 C13 N1 110.78(18) . . ?
C6 C13 N1 108.5(2) . . ?
C6 C13 C9 114.13(18) . . ?
H13 C13 N1 107.75(12) . . ?
H13 C13 C9 107.75(12) . . ?
H13 C13 C6 107.75(13) . . ?
H4a C4 C14 109.5 . . ?
H4b C4 C14 109.5 . . ?
H4b C4 H4a 109.5 . . ?
H4c C4 C14 109.5 . . ?
H4c C4 H4a 109.5 . . ?
H4c C4 H4b 109.5 . . ?
H5a C5 C3 118(2) . . ?
H5b C5 C3 120(2) . . ?
H5b C5 H5a 121(3) . . ?
C13 C6 C3 112.4(2) . . ?
H6a C6 C3 109.11(15) . . ?
H6a C6 C13 109.11(12) . . ?
H6b C6 C3 109.11(16) . . ?
H6b C6 C13 109.11(13) . . ?
H6b C6 H6a 107.8 . . ?
C4 C14 S 110.45(19) . . ?
C15 C14 S 103.05(19) . . ?
C15 C14 C4 109.8(3) . . ?
C16 C14 S 108.7(2) . . ?
C16 C14 C4 112.8(3) . . ?
C16 C14 C15 111.6(3) . . ?
H18a C18 O2 109.5 . . ?
H18b C18 O2 109.5 . . ?
H18b C18 H18a 109.5 . . ?
H18c C18 O2 109.5 . . ?
H18c C18 H18a 109.5 . . ?
H18c C18 H18b 109.5 . . ?
H15a C15 C14 109.5 . . ?
H15b C15 C14 109.5 . . ?
H15b C15 H15a 109.5 . . ?
H15c C15 C14 109.5 . . ?
H15c C15 H15a 109.5 . . ?
H15c C15 H15b 109.5 . . ?
H20a C20 O3 109.5 . . ?
H20b C20 O3 109.5 . . ?
H20b C20 H20a 109.5 . . ?
H20c C20 O3 109.5 . . ?
H20c C20 H20a 109.5 . . ?
H20c C20 H20b 109.5 . . ?
H16a C16 C14 109.5 . . ?
H16b C16 C14 109.5 . . ?
H16b C16 H16a 109.5 . . ?
H16c C16 C14 109.5 . . ?
H16c C16 H16a 109.5 . . ?
H16c C16 H16b 109.5 . . ?

# The following lines are used to test the character set of files sent by
# network email or other means. They are not part of the CIF data set
# abcdefghijklmnopqrstuvwxyzABCDEFGHIJKLMNOPQRSTUVWXYZ0123456789
# !@#$%^&*()_+{}:"~<>?|\-=[];'`,./

# END of CIF
_database_code_depnum_ccdc_archive 'CCDC 1001554'
