# Electronic Supplementary Material (ESI) for CrystEngComm.
# 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_RC

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C12 H7 N O2 S2'
_chemical_formula_sum            'C12 H7 N O2 S2'
_chemical_formula_weight         261.31

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

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   Pbca

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'
'-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                   10.331(4)
_cell_length_b                   7.626(3)
_cell_length_c                   28.392(11)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     2237.0(16)
_cell_formula_units_Z            8
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    5030
_cell_measurement_theta_min      2.87
_cell_measurement_theta_max      27.43

_exptl_crystal_description       Prism
_exptl_crystal_colour            Red
_exptl_crystal_size_max          0.5000
_exptl_crystal_size_mid          0.4000
_exptl_crystal_size_min          0.3000
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.552
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1072
_exptl_absorpt_coefficient_mu    0.462
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   'SADABS (Sheldrick, 1996)'
_exptl_absorpt_correction_T_min  0.8484
_exptl_absorpt_correction_T_max  1.0000

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker P4'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         none
_diffrn_standards_interval_count none
_diffrn_standards_interval_time  none
_diffrn_standards_decay_%        none
_diffrn_reflns_number            14937
_diffrn_reflns_av_R_equivalents  0.0500
_diffrn_reflns_av_sigmaI/netI    0.0398
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -36
_diffrn_reflns_limit_l_max       34
_diffrn_reflns_theta_min         2.87
_diffrn_reflns_theta_max         27.43
_reflns_number_total             2534
_reflns_number_gt                2015
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Siemens SMART'
_computing_cell_refinement       'Siemens SMART'
_computing_data_reduction        'Siemens XPREP'
_computing_structure_solution    'Siemens SHELXTL'
_computing_structure_refinement  'Siemens SHELXTL'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.1729P)²+1.1276P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2534
_refine_ls_number_parameters     158
_refine_ls_number_restraints     2
_refine_ls_R_factor_ref          0.0918
_refine_ls_R_factor_gt           0.0825
_refine_ls_wR_factor_ref         0.2621
_refine_ls_wR_factor_gt          0.2540
_refine_ls_goodness_of_fit_ref   1.077
_refine_ls_restrained_S_all      1.077
_refine_ls_shift/su_max          0.014
_refine_ls_shift/su_mean         0.002

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.99918(10) 0.13583(17) 0.70242(4) 0.0557(4) Uani 1 1 d . . .
S2 S 0.57634(13) 0.42084(18) 0.54687(4) 0.0603(4) Uani 1 1 d . . .
O1 O 1.1321(3) 0.3217(6) 0.62294(13) 0.0729(11) Uani 1 1 d . . .
O2 O 0.8283(4) 0.4563(5) 0.51296(10) 0.0658(10) Uani 1 1 d . . .
N1 N 1.0060(4) 0.3891(6) 0.55851(14) 0.0563(10) Uani 1 1 d D . .
C4 C 0.8773(4) 0.4044(6) 0.54968(13) 0.0487(10) Uani 1 1 d . . .
C3 C 0.8052(4) 0.3495(4) 0.59364(11) 0.0363(7) Uani 1 1 d . . .
C2 C 0.8967(3) 0.3147(5) 0.62693(12) 0.0362(7) Uani 1 1 d . . .
C1 C 1.0276(4) 0.3395(6) 0.60477(16) 0.0517(10) Uani 1 1 d . . .
C5 C 0.8882(3) 0.2718(4) 0.67646(11) 0.0331(7) Uani 1 1 d . . .
C6 C 0.7899(3) 0.3428(4) 0.71153(9) 0.0268(6) Uani 1 1 d U . .
H6 H 0.7216 0.4195 0.7058 0.032 Uiso 1 1 calc R . .
C7 C 0.8275(4) 0.2628(6) 0.75607(13) 0.0492(9) Uani 1 1 d U . .
H7 H 0.7827 0.2854 0.7838 0.059 Uiso 1 1 calc R . .
C8 C 0.9313(5) 0.1534(6) 0.75508(15) 0.0536(11) Uani 1 1 d . . .
H8 H 0.9615 0.0939 0.7815 0.064 Uiso 1 1 calc R . .
C9 C 0.6661(4) 0.3406(4) 0.59372(11) 0.0361(7) Uani 1 1 d . . .
C11 C 0.4517(4) 0.2800(7) 0.61441(15) 0.0548(11) Uani 1 1 d . . .
H11 H 0.3838 0.2362 0.6324 0.066 Uiso 1 1 calc R . .
C10 C 0.5835(3) 0.2662(5) 0.62768(12) 0.0397(8) Uani 1 1 d . . .
H10 H 0.6119 0.2143 0.6555 0.048 Uiso 1 1 calc R . .
C12 C 0.4351(5) 0.3643(7) 0.57248(17) 0.0607(12) Uani 1 1 d . . .
H12 H 0.3544 0.3881 0.5594 0.073 Uiso 1 1 calc R . .
H1 H 1.058(6) 0.436(8) 0.539(2) 0.11(3) Uiso 1 1 d D . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
S1 0.0421(6) 0.0623(8) 0.0627(8) -0.0001(5) -0.0084(4) 0.0052(4)
S2 0.0606(7) 0.0746(9) 0.0457(6) 0.0161(5) -0.0136(4) -0.0024(6)
O1 0.0318(15) 0.102(3) 0.085(2) 0.017(2) 0.0121(14) -0.0071(17)
O2 0.071(2) 0.090(2) 0.0362(14) 0.0162(15) 0.0093(13) -0.0198(19)
N1 0.047(2) 0.071(2) 0.050(2) 0.0068(17) 0.0211(15) -0.0144(17)
C4 0.053(2) 0.052(2) 0.040(2) 0.0004(16) 0.0152(16) -0.0128(18)
C3 0.0390(18) 0.0368(17) 0.0331(16) -0.0002(13) 0.0071(12) -0.0055(13)
C2 0.0288(16) 0.0388(17) 0.0410(17) 0.0004(13) 0.0070(12) -0.0045(13)
C1 0.0367(19) 0.063(2) 0.056(2) 0.0003(19) 0.0155(16) -0.0063(18)
C5 0.0235(14) 0.0373(16) 0.0386(16) -0.0011(12) 0.0011(11) 0.0001(12)
C6 0.0293(14) 0.0366(15) 0.0144(11) 0.0025(10) -0.0067(9) -0.0034(11)
C7 0.051(2) 0.061(2) 0.0359(18) -0.0031(16) -0.0026(15) -0.0071(18)
C8 0.055(2) 0.058(2) 0.048(2) 0.0073(18) -0.0223(18) -0.0068(19)
C9 0.0397(18) 0.0372(17) 0.0313(16) -0.0003(12) -0.0018(12) -0.0002(13)
C11 0.0325(18) 0.083(3) 0.049(2) -0.012(2) -0.0003(15) -0.001(2)
C10 0.0291(16) 0.053(2) 0.0374(17) 0.0016(15) -0.0029(12) -0.0003(14)
C12 0.044(2) 0.078(3) 0.061(3) -0.001(2) -0.0175(19) 0.009(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_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 C8 1.657(5) . ?
S1 C5 1.712(3) . ?
S2 C12 1.687(5) . ?
S2 C9 1.733(3) . ?
O1 C1 1.204(6) . ?
O2 C4 1.224(5) . ?
N1 C4 1.359(6) . ?
N1 C1 1.385(6) . ?
N1 H1 0.84(2) . ?
C4 C3 1.512(5) . ?
C3 C2 1.362(5) . ?
C3 C9 1.440(5) . ?
C2 C5 1.446(5) . ?
C2 C1 1.504(5) . ?
C5 C6 1.522(4) . ?
C6 C7 1.457(5) . ?
C6 H6 0.9300 . ?
C7 C8 1.359(7) . ?
C7 H7 0.9300 . ?
C8 H8 0.9300 . ?
C9 C10 1.407(5) . ?
C11 C12 1.364(7) . ?
C11 C10 1.416(5) . ?
C11 H11 0.9300 . ?
C10 H10 0.9300 . ?
C12 H12 0.9300 . ?

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
C8 S1 C5 93.2(2) . . ?
C12 S2 C9 92.4(2) . . ?
C4 N1 C1 110.9(3) . . ?
C4 N1 H1 118(5) . . ?
C1 N1 H1 128(5) . . ?
O2 C4 N1 126.1(4) . . ?
O2 C4 C3 126.1(4) . . ?
N1 C4 C3 107.8(4) . . ?
C2 C3 C9 133.0(3) . . ?
C2 C3 C4 106.6(3) . . ?
C9 C3 C4 120.4(3) . . ?
C3 C2 C5 132.6(3) . . ?
C3 C2 C1 108.0(3) . . ?
C5 C2 C1 119.3(3) . . ?
O1 C1 N1 125.6(4) . . ?
O1 C1 C2 127.8(4) . . ?
N1 C1 C2 106.7(4) . . ?
C2 C5 C6 126.6(3) . . ?
C2 C5 S1 121.0(2) . . ?
C6 C5 S1 112.4(2) . . ?
C7 C6 C5 103.9(3) . . ?
C7 C6 H6 128.0 . . ?
C5 C6 H6 128.0 . . ?
C8 C7 C6 116.7(4) . . ?
C8 C7 H7 121.6 . . ?
C6 C7 H7 121.6 . . ?
C7 C8 S1 113.7(3) . . ?
C7 C8 H8 123.1 . . ?
S1 C8 H8 123.1 . . ?
C10 C9 C3 128.7(3) . . ?
C10 C9 S2 110.1(3) . . ?
C3 C9 S2 121.1(2) . . ?
C12 C11 C10 112.9(4) . . ?
C12 C11 H11 123.6 . . ?
C10 C11 H11 123.6 . . ?
C9 C10 C11 111.8(3) . . ?
C9 C10 H10 124.1 . . ?
C11 C10 H10 124.1 . . ?
C11 C12 S2 112.8(3) . . ?
C11 C12 H12 123.6 . . ?
S2 C12 H12 123.6 . . ?

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 H1 O2 0.84(2) 2.07(2) 2.905(4) 174(7) 5_766
C6 H6 S1 0.93 2.82 3.739(4) 171.2 7_765

_diffrn_measured_fraction_theta_max 0.995
_diffrn_reflns_theta_full        27.43
_diffrn_measured_fraction_theta_full 0.995
_refine_diff_density_max         1.026
_refine_diff_density_min         -0.865
_refine_diff_density_rms         0.100
_database_code_depnum_ccdc_archive 'CCDC 946646'
#######################################################################
#
#                 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_OC

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C12 H7 N O2 S2'
_chemical_formula_sum            'C12 H7 N O2 S2'
_chemical_formula_weight         261.31

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

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P2(1)/n

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

_cell_length_a                   11.228(4)
_cell_length_b                   5.689(2)
_cell_length_c                   17.281(7)
_cell_angle_alpha                90.00
_cell_angle_beta                 94.745(6)
_cell_angle_gamma                90.00
_cell_volume                     1100.1(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    2951
_cell_measurement_theta_min      2.09
_cell_measurement_theta_max      27.48

_exptl_crystal_description       Prism
_exptl_crystal_colour            Colorless
_exptl_crystal_size_max          0.2000
_exptl_crystal_size_mid          0.2000
_exptl_crystal_size_min          0.2000
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.578
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             536
_exptl_absorpt_coefficient_mu    0.469
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick, 1996)'
_exptl_absorpt_correction_T_min  0.9257
_exptl_absorpt_correction_T_max  1.0000

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker P4'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         none
_diffrn_standards_interval_count none
_diffrn_standards_interval_time  none
_diffrn_standards_decay_%        none
_diffrn_reflns_number            7911
_diffrn_reflns_av_R_equivalents  0.0138
_diffrn_reflns_av_sigmaI/netI    0.0135
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         2.09
_diffrn_reflns_theta_max         27.48
_reflns_number_total             2488
_reflns_number_gt                2268
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Siemens SMART'
_computing_cell_refinement       'Siemens SMART'
_computing_data_reduction        'Siemens XPREP'
_computing_structure_solution    'Siemens SHELXTL'
_computing_structure_refinement  'Siemens SHELXTL'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0624P)²+0.7873P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2488
_refine_ls_number_parameters     154
_refine_ls_number_restraints     0
_refine_ls_R_factor_ref          0.0472
_refine_ls_R_factor_gt           0.0437
_refine_ls_wR_factor_ref         0.1225
_refine_ls_wR_factor_gt          0.1191
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_restrained_S_all      1.043
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.60872(6) 0.16106(13) 0.86787(4) 0.0614(2) Uani 1 1 d . . .
S2 S 0.73044(5) -0.32316(11) 1.16903(3) 0.0494(2) Uani 1 1 d . . .
O1 O 0.90832(13) 0.3567(3) 0.92281(8) 0.0438(4) Uani 1 1 d . . .
O2 O 0.90736(14) 0.0491(3) 1.16550(8) 0.0491(4) Uani 1 1 d . . .
C4 C 0.88444(16) 0.0747(3) 1.09665(10) 0.0331(4) Uani 1 1 d . . .
C5 C 0.72356(15) -0.0228(3) 0.89864(10) 0.0300(4) Uani 1 1 d . . .
C2 C 0.79668(15) 0.0297(3) 0.97132(10) 0.0290(4) Uani 1 1 d . . .
C3 C 0.79838(15) -0.0681(3) 1.04298(9) 0.0292(4) Uani 1 1 d . . .
N1 N 0.93187(14) 0.2441(3) 1.05132(9) 0.0367(4) Uani 1 1 d . . .
H1 H 0.9849 0.3451 1.0680 0.044 Uiso 1 1 calc R . .
C10 C 0.66528(16) -0.4276(3) 1.02739(10) 0.0342(4) Uani 1 1 d . . .
H10 H 0.6546 -0.4263 0.9734 0.041 Uiso 1 1 calc R . .
C1 C 0.88260(16) 0.2300(3) 0.97531(10) 0.0327(4) Uani 1 1 d . . .
C8 C 0.5748(2) -0.0006(5) 0.78627(12) 0.0489(5) Uani 1 1 d . . .
H8 H 0.5127 0.0354 0.7492 0.059 Uiso 1 1 calc R . .
C9 C 0.73350(15) -0.2638(3) 1.07074(10) 0.0306(4) Uani 1 1 d . . .
C6 C 0.7360(2) -0.2039(4) 0.84583(11) 0.0447(5) Uani 1 1 d . . .
H6 H 0.7937 -0.3213 0.8513 0.054 Uiso 1 1 calc R . .
C7 C 0.6467(2) -0.1833(4) 0.78146(12) 0.0484(5) Uani 1 1 d . . .
H7 H 0.6401 -0.2889 0.7402 0.058 Uiso 1 1 calc R . .
C11 C 0.61388(17) -0.5964(4) 1.07422(12) 0.0394(4) Uani 1 1 d . . .
H11 H 0.5667 -0.7202 1.0543 0.047 Uiso 1 1 calc R . .
C12 C 0.64016(19) -0.5598(4) 1.15116(12) 0.0448(5) Uani 1 1 d . . .
H12 H 0.6120 -0.6535 1.1898 0.054 Uiso 1 1 calc R . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
S1 0.0596(4) 0.0630(4) 0.0567(4) -0.0191(3) -0.0240(3) 0.0232(3)
S2 0.0629(4) 0.0583(4) 0.0256(3) 0.0047(2) -0.0047(2) -0.0190(3)
O1 0.0504(8) 0.0450(8) 0.0350(7) 0.0057(6) -0.0019(6) -0.0139(7)
O2 0.0567(9) 0.0592(10) 0.0291(7) 0.0007(6) -0.0096(6) -0.0122(8)
C4 0.0326(8) 0.0363(10) 0.0293(8) -0.0027(7) -0.0027(7) 0.0003(7)
C5 0.0333(8) 0.0309(9) 0.0250(8) 0.0020(6) -0.0014(6) -0.0020(7)
C2 0.0294(8) 0.0302(9) 0.0270(8) -0.0020(6) -0.0006(6) 0.0011(7)
C3 0.0288(8) 0.0323(9) 0.0260(8) -0.0025(7) -0.0014(6) 0.0027(7)
N1 0.0361(8) 0.0407(9) 0.0320(8) -0.0021(7) -0.0057(6) -0.0087(7)
C10 0.0361(9) 0.0372(10) 0.0291(8) -0.0028(7) 0.0017(7) -0.0012(7)
C1 0.0321(8) 0.0354(9) 0.0299(8) -0.0019(7) -0.0009(7) -0.0005(7)
C8 0.0474(11) 0.0627(14) 0.0339(10) 0.0007(10) -0.0134(8) -0.0044(11)
C9 0.0317(8) 0.0349(9) 0.0246(8) 0.0000(7) -0.0008(6) 0.0018(7)
C6 0.0630(13) 0.0431(11) 0.0257(9) -0.0063(8) -0.0110(8) 0.0078(10)
C7 0.0639(13) 0.0523(13) 0.0273(9) -0.0083(9) -0.0062(9) -0.0049(11)
C11 0.0362(9) 0.0372(10) 0.0440(10) 0.0005(8) -0.0007(8) -0.0032(8)
C12 0.0453(11) 0.0500(12) 0.0386(10) 0.0127(9) -0.0004(8) -0.0082(9)

_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
S1 C8 1.700(2) . ?
S1 C5 1.7107(19) . ?
S2 C12 1.698(2) . ?
S2 C9 1.7350(19) . ?
O1 C1 1.212(2) . ?
O2 C4 1.205(2) . ?
C4 N1 1.377(3) . ?
C4 C3 1.518(2) . ?
C5 C6 1.391(3) . ?
C5 C2 1.473(2) . ?
C2 C3 1.356(2) . ?
C2 C1 1.491(3) . ?
C3 C9 1.435(3) . ?
N1 C1 1.385(2) . ?
N1 H1 0.8600 . ?
C10 C9 1.386(3) . ?
C10 C11 1.410(3) . ?
C10 H10 0.9300 . ?
C8 C7 1.323(4) . ?
C8 H8 0.9300 . ?
C6 C7 1.439(3) . ?
C6 H6 0.9300 . ?
C7 H7 0.9300 . ?
C11 C12 1.354(3) . ?
C11 H11 0.9300 . ?
C12 H12 0.9300 . ?

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
C8 S1 C5 92.20(11) . . ?
C12 S2 C9 92.08(10) . . ?
O2 C4 N1 125.81(17) . . ?
O2 C4 C3 127.71(18) . . ?
N1 C4 C3 106.47(15) . . ?
C6 C5 C2 129.11(17) . . ?
C6 C5 S1 111.27(14) . . ?
C2 C5 S1 119.57(13) . . ?
C3 C2 C5 131.28(17) . . ?
C3 C2 C1 108.13(15) . . ?
C5 C2 C1 120.50(15) . . ?
C2 C3 C9 130.88(16) . . ?
C2 C3 C4 107.36(16) . . ?
C9 C3 C4 121.74(15) . . ?
C4 N1 C1 110.87(15) . . ?
C4 N1 H1 124.6 . . ?
C1 N1 H1 124.6 . . ?
C9 C10 C11 112.46(17) . . ?
C9 C10 H10 123.8 . . ?
C11 C10 H10 123.8 . . ?
O1 C1 N1 125.05(18) . . ?
O1 C1 C2 127.82(17) . . ?
N1 C1 C2 107.11(15) . . ?
C7 C8 S1 112.41(16) . . ?
C7 C8 H8 123.8 . . ?
S1 C8 H8 123.8 . . ?
C10 C9 C3 127.90(16) . . ?
C10 C9 S2 110.08(14) . . ?
C3 C9 S2 122.02(13) . . ?
C5 C6 C7 110.23(19) . . ?
C5 C6 H6 124.9 . . ?
C7 C6 H6 124.9 . . ?
C8 C7 C6 113.88(19) . . ?
C8 C7 H7 123.1 . . ?
C6 C7 H7 123.1 . . ?
C12 C11 C10 113.12(19) . . ?
C12 C11 H11 123.4 . . ?
C10 C11 H11 123.4 . . ?
C11 C12 S2 112.26(16) . . ?
C11 C12 H12 123.9 . . ?
S2 C12 H12 123.9 . . ?

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 H1 O1 0.86 2.08 2.906(2) 162.1 3_767
C6 H6 O1 0.93 2.51 3.367(3) 154.3 1_545

_diffrn_measured_fraction_theta_max 0.983
_diffrn_reflns_theta_full        27.48
_diffrn_measured_fraction_theta_full 0.983
_refine_diff_density_max         0.415
_refine_diff_density_min         -0.621
_refine_diff_density_rms         0.053
_database_code_depnum_ccdc_archive 'CCDC 946647'
