# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2014

#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_R28

_audit_creation_date             2013-07-03T13:30:35-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4.3
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic
#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C14 H19 N1 O5 S1'
_chemical_formula_sum            'C14 H19 N O5 S'
_chemical_formula_weight         313.36
_chemical_compound_source        'synthesis as described'
_chemical_absolute_configuration ad

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

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21'
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_Int_Tables_number      4
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   10.9779(7)
_cell_length_b                   5.7869(5)
_cell_length_c                   12.1402(10)
_cell_angle_alpha                90
_cell_angle_beta                 92.349(4)
_cell_angle_gamma                90
_cell_volume                     770.59(10)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    1982
_cell_measurement_theta_min      3.36
_cell_measurement_theta_max      26.21
_cell_measurement_wavelength     0.71073

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

_exptl_crystal_description       Needle
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.08
_exptl_crystal_density_diffrn    1.351
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             332
_exptl_special_details           
;
 ?
;

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

_exptl_absorpt_coefficient_mu    0.23
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'BRUKER SADABS'
_exptl_absorpt_correction_T_min  0.9163
_exptl_absorpt_correction_T_max  0.9659

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

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.7107
_diffrn_radiation_type           MoK\a
_diffrn_radiation_probe          x-ray
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'BRUKER APPEX-II CCD'
_diffrn_measurement_method       'omega and phi scans'
_diffrn_reflns_av_R_equivalents  0.0367
_diffrn_reflns_number            11862
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.452
_diffrn_reflns_theta_max         26.441
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.993
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.992
_reflns_number_total             3156
_reflns_number_gt                2970
_reflns_threshold_expression     'I > 2σ(I)'

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#
_computing_data_collection       'APPEX2 (BRUKER AXS, 2005)'
_computing_cell_refinement       'APPEX2 (BRUKER AXS, 2005)'
_computing_data_reduction        'APPEX2 (BRUKER AXS, 2005)'
_computing_structure_solution    'SIR97 (Giacovazzo et al, 1997)'
_computing_structure_refinement  'SHELXL-2012 (Sheldrick, 2012)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'

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

_atom_sites_solution_hydrogens   mixed

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

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
 w=1/[σ²(Fo²)+(0.0334P)²+0.1250P]
 where P=(Fo²+2Fc²)/3
;
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_number_reflns         3156
_refine_ls_number_parameters     196
_refine_ls_number_restraints     2
_refine_ls_number_constraints    0
_refine_ls_R_factor_all          0.0357
_refine_ls_R_factor_gt           0.0325
_refine_ls_wR_factor_ref         0.0695
_refine_ls_wR_factor_gt          0.068
_refine_ls_goodness_of_fit_ref   1.014
_refine_ls_restrained_S_all      1.015
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_ls_abs_structure_details 
;
 Flack x determined using 1250 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   0.03(4)
_refine_diff_density_max         0.212
_refine_diff_density_min         -0.297
_refine_diff_density_rms         0.043

#----------------------------------------------------------------------------#
#                   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'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.006 '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'

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_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.3548(2) 0.6882(4) 0.8025(2) 0.0114(5) Uani 1 d . .
C2 C 0.4517(2) 0.5108(5) 0.7741(2) 0.0142(6) Uani 1 d . .
H2A H 0.453 0.3807 0.827 0.017 Uiso 1 calc . .
H2B H 0.4362 0.4492 0.6987 0.017 Uiso 1 calc . .
C3 C 0.23687(19) 0.5667(5) 0.8377(2) 0.0136(5) Uani 1 d . .
H3A H 0.2181 0.4388 0.7856 0.016 Uiso 1 calc . .
H3B H 0.2524 0.4977 0.9116 0.016 Uiso 1 calc . .
C4 C 0.1264(2) 0.7216(5) 0.8418(2) 0.0144(6) Uani 1 d . .
C5 C 0.1266(2) 0.9232(5) 0.9037(2) 0.0180(6) Uani 1 d . .
H5 H 0.1984 0.9663 0.945 0.022 Uiso 1 calc . .
C6 C 0.0239(2) 1.0636(5) 0.9066(2) 0.0216(6) Uani 1 d . .
H6 H 0.0269 1.2035 0.9476 0.026 Uiso 1 calc . .
C7 C -0.0825(2) 0.9995(5) 0.8498(2) 0.0241(7) Uani 1 d . .
H7 H -0.1531 1.0938 0.8521 0.029 Uiso 1 calc . .
C8 C -0.0850(2) 0.7963(6) 0.7894(2) 0.0245(7) Uani 1 d . .
H8 H -0.1581 0.7501 0.7511 0.029 Uiso 1 calc . .
C9 C 0.0182(2) 0.6603(5) 0.7845(2) 0.0189(6) Uani 1 d . .
H9 H 0.0155 0.5231 0.7415 0.023 Uiso 1 calc . .
C10 C 0.32468(19) 0.8557(5) 0.7075(2) 0.0130(6) Uani 1 d . .
C11 C 0.2540(2) 0.8686(5) 0.5132(2) 0.0225(7) Uani 1 d . .
C12 C 0.1380(2) 1.0023(6) 0.5330(3) 0.0310(8) Uani 1 d . .
H12A H 0.076 0.8967 0.5598 0.046 Uiso 1 calc . .
H12B H 0.1081 1.0735 0.4638 0.046 Uiso 1 calc . .
H12C H 0.1551 1.123 0.5881 0.046 Uiso 1 calc . .
C13 C 0.3569(3) 1.0238(7) 0.4785(2) 0.0333(8) Uani 1 d . .
H13A H 0.3666 1.1525 0.5306 0.05 Uiso 1 calc . .
H13B H 0.3379 1.0844 0.4044 0.05 Uiso 1 calc . .
H13C H 0.4328 0.9347 0.4781 0.05 Uiso 1 calc . .
C14 C 0.2302(4) 0.6749(7) 0.4316(3) 0.0528(11) Uani 1 d . .
H14A H 0.3051 0.5852 0.4238 0.079 Uiso 1 calc . .
H14B H 0.2041 0.7399 0.36 0.079 Uiso 1 calc . .
H14C H 0.1661 0.5739 0.4583 0.079 Uiso 1 calc . .
N1 N 0.41692(16) 0.8104(4) 0.89434(16) 0.0128(4) Uani 1 d . .
H1N H 0.395(2) 0.935(4) 0.918(2) 0.015 Uiso 1 d . .
S1 S 0.56472(5) 0.82069(11) 0.87831(5) 0.01262(15) Uani 1 d . .
O1 O 0.62652(15) 0.7287(3) 0.97444(15) 0.0184(4) Uani 1 d . .
O2 O 0.60822(15) 1.0354(3) 0.83820(15) 0.0205(4) Uani 1 d . .
O3 O 0.56680(14) 0.6388(3) 0.78155(15) 0.0173(4) Uani 1 d . .
O4 O 0.32792(15) 1.0630(3) 0.71761(15) 0.0182(4) Uani 1 d . .
O5 O 0.29212(15) 0.7411(3) 0.61589(14) 0.0178(4) Uani 1 d . .



#----------------------------------------------------------------------------#
#                   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
C1 N1 1.465(3) . ?
C1 C2 1.529(3) . ?
C1 C10 1.532(4) . ?
C1 C3 1.549(3) . ?
C2 O3 1.464(3) . ?
C2 H2A 0.99 . ?
C2 H2B 0.99 . ?
C3 C4 1.511(3) . ?
C3 H3A 0.99 . ?
C3 H3B 0.99 . ?
C4 C5 1.388(4) . ?
C4 C9 1.397(4) . ?
C5 C6 1.391(4) . ?
C5 H5 0.95 . ?
C6 C7 1.383(4) . ?
C6 H6 0.95 . ?
C7 C8 1.385(4) . ?
C7 H7 0.95 . ?
C8 C9 1.383(4) . ?
C8 H8 0.95 . ?
C9 H9 0.95 . ?
C10 O4 1.206(3) . ?
C10 O5 1.331(3) . ?
C11 O5 1.494(3) . ?
C11 C14 1.511(4) . ?
C11 C12 1.517(4) . ?
C11 C13 1.516(4) . ?
C12 H12A 0.98 . ?
C12 H12B 0.98 . ?
C12 H12C 0.98 . ?
C13 H13A 0.98 . ?
C13 H13B 0.98 . ?
C13 H13C 0.98 . ?
C14 H14A 0.98 . ?
C14 H14B 0.98 . ?
C14 H14C 0.98 . ?
N1 S1 1.6432(18) . ?
N1 H1N 0.82(2) . ?
S1 O2 1.424(2) . ?
S1 O1 1.4287(18) . ?
S1 O3 1.5781(19) . ?

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 C2 100.92(19) . . ?
N1 C1 C10 110.3(2) . . ?
C2 C1 C10 112.7(2) . . ?
N1 C1 C3 112.20(19) . . ?
C2 C1 C3 110.8(2) . . ?
C10 C1 C3 109.76(19) . . ?
O3 C2 C1 104.7(2) . . ?
O3 C2 H2A 110.8 . . ?
C1 C2 H2A 110.8 . . ?
O3 C2 H2B 110.8 . . ?
C1 C2 H2B 110.8 . . ?
H2A C2 H2B 108.9 . . ?
C4 C3 C1 114.9(2) . . ?
C4 C3 H3A 108.6 . . ?
C1 C3 H3A 108.6 . . ?
C4 C3 H3B 108.6 . . ?
C1 C3 H3B 108.6 . . ?
H3A C3 H3B 107.5 . . ?
C5 C4 C9 117.8(2) . . ?
C5 C4 C3 122.2(2) . . ?
C9 C4 C3 120.0(3) . . ?
C6 C5 C4 121.4(3) . . ?
C6 C5 H5 119.3 . . ?
C4 C5 H5 119.3 . . ?
C7 C6 C5 120.0(3) . . ?
C7 C6 H6 120 . . ?
C5 C6 H6 120 . . ?
C6 C7 C8 119.3(2) . . ?
C6 C7 H7 120.3 . . ?
C8 C7 H7 120.3 . . ?
C9 C8 C7 120.5(2) . . ?
C9 C8 H8 119.7 . . ?
C7 C8 H8 119.7 . . ?
C8 C9 C4 121.0(3) . . ?
C8 C9 H9 119.5 . . ?
C4 C9 H9 119.5 . . ?
O4 C10 O5 125.9(2) . . ?
O4 C10 C1 123.2(2) . . ?
O5 C10 C1 110.9(2) . . ?
O5 C11 C14 102.4(2) . . ?
O5 C11 C12 109.2(2) . . ?
C14 C11 C12 111.0(3) . . ?
O5 C11 C13 109.7(2) . . ?
C14 C11 C13 111.6(3) . . ?
C12 C11 C13 112.4(3) . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C11 C13 H13A 109.5 . . ?
C11 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C11 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C11 C14 H14A 109.5 . . ?
C11 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C11 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C1 N1 S1 111.02(15) . . ?
C1 N1 H1N 124.3(19) . . ?
S1 N1 H1N 108(2) . . ?
O2 S1 O1 116.74(11) . . ?
O2 S1 O3 108.19(11) . . ?
O1 S1 O3 109.79(11) . . ?
O2 S1 N1 114.75(12) . . ?
O1 S1 N1 109.14(11) . . ?
O3 S1 N1 96.23(10) . . ?
C2 O3 S1 110.18(14) . . ?
C10 O5 C11 120.5(2) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 C1 C2 O3 -41.3(2) . . . . ?
C10 C1 C2 O3 76.3(2) . . . . ?
C3 C1 C2 O3 -160.3(2) . . . . ?
N1 C1 C3 C4 81.7(3) . . . . ?
C2 C1 C3 C4 -166.3(2) . . . . ?
C10 C1 C3 C4 -41.3(3) . . . . ?
C1 C3 C4 C5 -55.0(3) . . . . ?
C1 C3 C4 C9 126.8(3) . . . . ?
C9 C4 C5 C6 -1.7(4) . . . . ?
C3 C4 C5 C6 -179.9(3) . . . . ?
C4 C5 C6 C7 2.1(4) . . . . ?
C5 C6 C7 C8 -0.7(4) . . . . ?
C6 C7 C8 C9 -1.0(4) . . . . ?
C7 C8 C9 C4 1.3(4) . . . . ?
C5 C4 C9 C8 0.0(4) . . . . ?
C3 C4 C9 C8 178.3(3) . . . . ?
N1 C1 C10 O4 -14.8(3) . . . . ?
C2 C1 C10 O4 -126.8(2) . . . . ?
C3 C1 C10 O4 109.3(3) . . . . ?
N1 C1 C10 O5 166.88(17) . . . . ?
C2 C1 C10 O5 54.9(2) . . . . ?
C3 C1 C10 O5 -69.0(2) . . . . ?
C2 C1 N1 S1 32.8(2) . . . . ?
C10 C1 N1 S1 -86.5(2) . . . . ?
C3 C1 N1 S1 150.77(18) . . . . ?
C1 N1 S1 O2 101.1(2) . . . . ?
C1 N1 S1 O1 -125.73(18) . . . . ?
C1 N1 S1 O3 -12.3(2) . . . . ?
C1 C2 O3 S1 36.0(2) . . . . ?
O2 S1 O3 C2 -133.44(16) . . . . ?
O1 S1 O3 C2 98.14(17) . . . . ?
N1 S1 O3 C2 -14.80(18) . . . . ?
O4 C10 O5 C11 -0.5(4) . . . . ?
C1 C10 O5 C11 177.67(19) . . . . ?
C14 C11 O5 C10 178.1(2) . . . . ?
C12 C11 O5 C10 -64.2(3) . . . . ?
C13 C11 O5 C10 59.5(3) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H1N O1 0.82(2) 2.16(2) 2.947(3) 162(3) 2_657

_database_code_depnum_ccdc_archive 'CCDC 958602'
#######################################################################
#
#                 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_R35

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

_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C14 H18 N4 O5 S1'
_chemical_formula_sum            'C14 H18 N4 O5 S'
_chemical_formula_weight         354.38
_chemical_compound_source        'synthesis as described'
_chemical_absolute_configuration ad

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

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'P 21 21 21'
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_Int_Tables_number      19
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'

_cell_length_a                   5.7297(3)
_cell_length_b                   16.2240(9)
_cell_length_c                   17.5243(9)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1629.04(15)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    1996
_cell_measurement_theta_min      2.64
_cell_measurement_theta_max      25.68
_cell_measurement_wavelength     0.71073

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

_exptl_crystal_description       Needle
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.27
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.04
_exptl_crystal_density_diffrn    1.445
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             744
_exptl_special_details           
;
 ?
;

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

_exptl_absorpt_coefficient_mu    0.232
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'BRUKER SADABS'
_exptl_absorpt_correction_T_min  0.8083
_exptl_absorpt_correction_T_max  0.9705

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

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.7107
_diffrn_radiation_type           MoK\a
_diffrn_radiation_probe          x-ray
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'BRUKER APPEX-II CCD'
_diffrn_measurement_method       'omega and phi scans'
_diffrn_reflns_av_R_equivalents  0.0524
_diffrn_reflns_number            8190
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         2.324
_diffrn_reflns_theta_max         26.462
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.997
_reflns_number_total             3347
_reflns_number_gt                2496
_reflns_threshold_expression     'I > 2σ(I)'

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

_computing_data_collection       'APPEX2 (BRUKER AXS, 2005)'
_computing_cell_refinement       'APPEX2 (BRUKER AXS, 2005)'
_computing_data_reduction        'APPEX2 (BRUKER AXS, 2005)'
_computing_structure_solution    'SIR97 (Giacovazzo et al, 1997)'
_computing_structure_refinement  'SHELXL-2012 (Sheldrick, 2012)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'

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

_atom_sites_solution_hydrogens   mixed

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

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
 w=1/[σ²(Fo²)+(0.0656P)²]
 where P=(Fo²+2Fc²)/3
;
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_number_reflns         3347
_refine_ls_number_parameters     223
_refine_ls_number_restraints     4
_refine_ls_number_constraints    0
_refine_ls_R_factor_all          0.0762
_refine_ls_R_factor_gt           0.0465
_refine_ls_wR_factor_ref         0.1098
_refine_ls_wR_factor_gt          0.0949
_refine_ls_goodness_of_fit_ref   0.854
_refine_ls_restrained_S_all      0.854
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_ls_abs_structure_details 
;
 Flack x determined using 830 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   0.10(8)
_refine_diff_density_max         0.251
_refine_diff_density_min         -0.344
_refine_diff_density_rms         0.059

#----------------------------------------------------------------------------#
#                   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'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.006 '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'

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_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.1528(7) -0.0998(2) -0.0831(2) 0.0132(9) Uani 1 d . .
C2 C -0.0141(8) -0.1456(2) -0.1366(2) 0.0151(10) Uani 1 d . .
H2A H -0.1523 -0.166 -0.1085 0.018 Uiso 1 calc . .
H2B H -0.067 -0.1092 -0.1786 0.018 Uiso 1 calc . .
C3 C 0.0192(7) -0.0442(2) -0.0267(2) 0.0136(9) Uani 1 d . .
H3A H -0.109 -0.0165 -0.0546 0.016 Uiso 1 calc . .
H3B H -0.0527 -0.0795 0.0129 0.016 Uiso 1 calc . .
C4 C 0.1647(7) 0.0209(3) 0.0124(2) 0.0137(9) Uani 1 d . .
C5 C 0.3602(8) 0.0006(3) 0.0559(2) 0.0186(10) Uani 1 d . .
H5 H 0.4021 -0.0557 0.0617 0.022 Uiso 1 calc . .
C6 C 0.4942(8) 0.0605(3) 0.0907(2) 0.0204(10) Uani 1 d . .
H6 H 0.6279 0.0454 0.1196 0.025 Uiso 1 calc . .
C7 C 0.4325(8) 0.1431(3) 0.0834(2) 0.0206(11) Uani 1 d . .
C8 C 0.2403(9) 0.1647(3) 0.0411(2) 0.0237(11) Uani 1 d . .
H8 H 0.1974 0.221 0.0363 0.028 Uiso 1 calc . .
C9 C 0.1085(9) 0.1040(3) 0.0053(2) 0.0209(11) Uani 1 d . .
H9 H -0.0225 0.1195 -0.0246 0.025 Uiso 1 calc . .
C10 C 0.3305(8) -0.0478(2) -0.1280(2) 0.0128(9) Uani 1 d . .
C11 C 0.3517(8) 0.0705(3) -0.2161(2) 0.0163(10) Uani 1 d . .
C12 C 0.4998(9) 0.1238(3) -0.1638(3) 0.0237(11) Uani 1 d . .
H12A H 0.6229 0.0901 -0.1407 0.036 Uiso 1 calc . .
H12B H 0.4013 0.1472 -0.1235 0.036 Uiso 1 calc . .
H12C H 0.5706 0.1686 -0.1934 0.036 Uiso 1 calc . .
C13 C 0.4965(9) 0.0261(3) -0.2761(2) 0.0225(11) Uani 1 d . .
H13A H 0.3996 -0.0152 -0.3018 0.034 Uiso 1 calc . .
H13B H 0.6292 -0.0013 -0.2514 0.034 Uiso 1 calc . .
H13C H 0.554 0.066 -0.3136 0.034 Uiso 1 calc . .
C14 C 0.1550(8) 0.1196(3) -0.2511(3) 0.0223(11) Uani 1 d . .
H14A H 0.0585 0.1434 -0.2105 0.033 Uiso 1 calc . .
H14B H 0.059 0.0833 -0.2829 0.033 Uiso 1 calc . .
H14C H 0.2198 0.164 -0.2826 0.033 Uiso 1 calc . .
N2 N 0.5617(8) 0.2092(2) 0.1191(2) 0.0277(9) Uani 1 d . .
N3 N 0.7190(8) 0.1878(2) 0.1619(2) 0.0256(9) Uani 1 d . .
N4 N 0.8685(8) 0.1767(3) 0.2032(2) 0.0340(11) Uani 1 d . .
N1 N 0.2688(6) -0.1693(2) -0.04487(18) 0.0131(8) Uani 1 d . .
H1N H 0.391(6) -0.158(3) -0.021(2) 0.016 Uiso 1 d . .
S1 S 0.27944(17) -0.25043(7) -0.09999(5) 0.0135(2) Uani 1 d . .
O1 O 0.1594(5) -0.31745(17) -0.06447(17) 0.0206(8) Uani 1 d . .
O2 O 0.5056(5) -0.26858(17) -0.12939(16) 0.0197(7) Uani 1 d . .
O3 O 0.1248(5) -0.21409(18) -0.16616(16) 0.0170(7) Uani 1 d . .
O4 O 0.5389(5) -0.05787(18) -0.12328(16) 0.0173(7) Uani 1 d . .
O5 O 0.2205(5) 0.00853(16) -0.16959(14) 0.0143(6) Uani 1 d . .



#----------------------------------------------------------------------------#
#                   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
C1 N1 1.471(5) . ?
C1 C10 1.538(6) . ?
C1 C2 1.532(6) . ?
C1 C3 1.542(5) . ?
C2 O3 1.462(5) . ?
C2 H2A 0.99 . ?
C2 H2B 0.99 . ?
C3 C4 1.509(6) . ?
C3 H3A 0.99 . ?
C3 H3B 0.99 . ?
C4 C5 1.394(6) . ?
C4 C9 1.391(6) . ?
C5 C6 1.381(6) . ?
C5 H5 0.95 . ?
C6 C7 1.392(6) . ?
C6 H6 0.95 . ?
C7 C8 1.373(6) . ?
C7 N2 1.446(6) . ?
C8 C9 1.391(6) . ?
C8 H8 0.95 . ?
C9 H9 0.95 . ?
C10 O4 1.208(5) . ?
C10 O5 1.328(5) . ?
C11 O5 1.497(5) . ?
C11 C12 1.519(6) . ?
C11 C13 1.521(6) . ?
C11 C14 1.511(6) . ?
C12 H12A 0.98 . ?
C12 H12B 0.98 . ?
C12 H12C 0.98 . ?
C13 H13A 0.98 . ?
C13 H13B 0.98 . ?
C13 H13C 0.98 . ?
C14 H14A 0.98 . ?
C14 H14B 0.98 . ?
C14 H14C 0.98 . ?
N2 N3 1.223(5) . ?
N3 N4 1.136(6) . ?
N1 S1 1.634(3) . ?
N1 H1N 0.84(2) . ?
S1 O2 1.425(3) . ?
S1 O1 1.429(3) . ?
S1 O3 1.574(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
N1 C1 C10 110.7(3) . . ?
N1 C1 C2 100.9(3) . . ?
C10 C1 C2 111.4(3) . . ?
N1 C1 C3 112.4(3) . . ?
C10 C1 C3 109.7(3) . . ?
C2 C1 C3 111.5(4) . . ?
O3 C2 C1 104.2(3) . . ?
O3 C2 H2A 110.9 . . ?
C1 C2 H2A 110.9 . . ?
O3 C2 H2B 110.9 . . ?
C1 C2 H2B 110.9 . . ?
H2A C2 H2B 108.9 . . ?
C4 C3 C1 115.2(4) . . ?
C4 C3 H3A 108.5 . . ?
C1 C3 H3A 108.5 . . ?
C4 C3 H3B 108.5 . . ?
C1 C3 H3B 108.5 . . ?
H3A C3 H3B 107.5 . . ?
C5 C4 C9 117.6(4) . . ?
C5 C4 C3 121.8(4) . . ?
C9 C4 C3 120.6(4) . . ?
C6 C5 C4 121.5(4) . . ?
C6 C5 H5 119.2 . . ?
C4 C5 H5 119.2 . . ?
C5 C6 C7 119.7(4) . . ?
C5 C6 H6 120.2 . . ?
C7 C6 H6 120.2 . . ?
C8 C7 C6 119.9(4) . . ?
C8 C7 N2 117.1(4) . . ?
C6 C7 N2 123.0(4) . . ?
C7 C8 C9 119.9(4) . . ?
C7 C8 H8 120.1 . . ?
C9 C8 H8 120.1 . . ?
C8 C9 C4 121.4(4) . . ?
C8 C9 H9 119.3 . . ?
C4 C9 H9 119.3 . . ?
O4 C10 O5 126.8(4) . . ?
O4 C10 C1 123.0(4) . . ?
O5 C10 C1 110.1(4) . . ?
O5 C11 C12 109.6(3) . . ?
O5 C11 C13 109.3(3) . . ?
C12 C11 C13 112.5(4) . . ?
O5 C11 C14 101.6(3) . . ?
C12 C11 C14 111.2(4) . . ?
C13 C11 C14 112.1(4) . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C11 C13 H13A 109.5 . . ?
C11 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C11 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C11 C14 H14A 109.5 . . ?
C11 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C11 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
N3 N2 C7 115.6(4) . . ?
N4 N3 N2 172.7(5) . . ?
C1 N1 S1 111.5(2) . . ?
C1 N1 H1N 116(3) . . ?
S1 N1 H1N 116(3) . . ?
O2 S1 O1 115.96(18) . . ?
O2 S1 O3 108.84(17) . . ?
O1 S1 O3 109.58(18) . . ?
O2 S1 N1 114.47(18) . . ?
O1 S1 N1 109.72(17) . . ?
O3 S1 N1 96.47(16) . . ?
C2 O3 S1 109.3(2) . . ?
C10 O5 C11 121.5(3) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 C1 C2 O3 -41.3(4) . . . . ?
C10 C1 C2 O3 76.2(4) . . . . ?
C3 C1 C2 O3 -160.9(3) . . . . ?
N1 C1 C3 C4 84.4(4) . . . . ?
C10 C1 C3 C4 -39.3(5) . . . . ?
C2 C1 C3 C4 -163.2(3) . . . . ?
C1 C3 C4 C5 -57.8(5) . . . . ?
C1 C3 C4 C9 121.6(4) . . . . ?
C9 C4 C5 C6 -0.1(6) . . . . ?
C3 C4 C5 C6 179.2(4) . . . . ?
C4 C5 C6 C7 0.9(7) . . . . ?
C5 C6 C7 C8 -0.6(7) . . . . ?
C5 C6 C7 N2 179.0(4) . . . . ?
C6 C7 C8 C9 -0.4(7) . . . . ?
N2 C7 C8 C9 180.0(4) . . . . ?
C7 C8 C9 C4 1.1(7) . . . . ?
C5 C4 C9 C8 -0.8(6) . . . . ?
C3 C4 C9 C8 179.8(4) . . . . ?
N1 C1 C10 O4 -8.9(5) . . . . ?
C2 C1 C10 O4 -120.4(4) . . . . ?
C3 C1 C10 O4 115.7(4) . . . . ?
N1 C1 C10 O5 172.4(3) . . . . ?
C2 C1 C10 O5 61.0(4) . . . . ?
C3 C1 C10 O5 -62.9(4) . . . . ?
C8 C7 N2 N3 173.7(4) . . . . ?
C6 C7 N2 N3 -6.0(7) . . . . ?
C10 C1 N1 S1 -89.0(3) . . . . ?
C2 C1 N1 S1 29.1(4) . . . . ?
C3 C1 N1 S1 148.0(3) . . . . ?
C1 N1 S1 O2 107.4(3) . . . . ?
C1 N1 S1 O1 -120.2(3) . . . . ?
C1 N1 S1 O3 -6.7(3) . . . . ?
C1 C2 O3 S1 39.9(4) . . . . ?
O2 S1 O3 C2 -138.9(3) . . . . ?
O1 S1 O3 C2 93.3(3) . . . . ?
N1 S1 O3 C2 -20.3(3) . . . . ?
O4 C10 O5 C11 -1.7(6) . . . . ?
C1 C10 O5 C11 176.9(3) . . . . ?
C12 C11 O5 C10 -61.9(5) . . . . ?
C13 C11 O5 C10 61.9(5) . . . . ?
C14 C11 O5 C10 -179.5(3) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H1N O1 0.84(2) 2.18(3) 2.954(4) 153(4) 3_545

_database_code_depnum_ccdc_archive 'CCDC 958603'
