# Electronic Supplementary Material (ESI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 2017

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_v73c
_database_code_depnum_ccdc_archive 'CCDC 1513686'
_audit_update_record             
;
2016-10-31 deposited with the CCDC.
2017-10-02 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C9 H9 N O S'
_chemical_formula_weight         179.23

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 21'
_space_group_name_Hall           'P 2yb'

_shelx_space_group_comment       
; 
The symmetry employed for this shelxl refinement is uniquely defined 
by the following loop, which should always be used as a source of 
symmetry information in preference to the above space-group names. 
They are only intended as comments. 
;

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

_cell_length_a                   5.8614(10)
_cell_length_b                   27.535(5)
_cell_length_c                   5.9676(10)
_cell_angle_alpha                90
_cell_angle_beta                 119.351(2)
_cell_angle_gamma                90
_cell_volume                     839.5(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    4480
_cell_measurement_theta_min      4.82
_cell_measurement_theta_max      67.65

_exptl_crystal_description       Near
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.418
_exptl_crystal_F_000             376
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.500
_exptl_crystal_size_mid          0.450
_exptl_crystal_size_min          0.420
_exptl_absorpt_coefficient_mu    2.984
_shelx_estimated_absorpt_T_min   0.317
_shelx_estimated_absorpt_T_max   0.367
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.654
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker Platinum 135 CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            4298
_diffrn_reflns_av_unetI/netI     0.0574
_diffrn_reflns_av_R_equivalents  0.0387
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       32
_diffrn_reflns_limit_l_min       -6
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_theta_min         6.430
_diffrn_reflns_theta_max         67.649
_diffrn_reflns_theta_full        66.000
_diffrn_measured_fraction_theta_max 0.946
_diffrn_measured_fraction_theta_full 0.966
_diffrn_reflns_Laue_measured_fraction_max 0.946
_diffrn_reflns_Laue_measured_fraction_full 0.966
_diffrn_reflns_point_group_measured_fraction_max 0.946
_diffrn_reflns_point_group_measured_fraction_full 0.966
_reflns_number_total             1923
_reflns_number_gt                1923
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.955
_reflns_Friedel_fraction_max     0.946
_reflns_Friedel_fraction_full    0.965

_reflns_special_details          
; 
 Reflections were merged by SHELXL according to the crystal 
 class for the calculation of statistics and refinement. 
  
 _reflns_Friedel_fraction is defined as the number of unique 
 Friedel pairs measured divided by the number that would be 
 possible theoretically, ignoring centric projections and 
 systematic absences. 
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 Refined as a 2-component inversion twin. 
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0869P)²+0.7157P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    refxyz
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.016(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 
; 
 Refined as an inversion twin. 
;
_refine_ls_abs_structure_Flack   0.17(4)
_chemical_absolute_configuration abs
_refine_ls_number_reflns         1923
_refine_ls_number_parameters     285
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0500
_refine_ls_R_factor_gt           0.0500
_refine_ls_wR_factor_ref         0.1283
_refine_ls_wR_factor_gt          0.1283
_refine_ls_goodness_of_fit_ref   1.085
_refine_ls_restrained_S_all      1.085
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.0649(2) 0.01007(5) -0.0157(2) 0.0153(4) Uani 1 1 d . . . . .
O1 O 0.6216(7) 0.12722(15) 0.1257(6) 0.0162(8) Uani 1 1 d . . . . .
N1 N -0.4250(9) 0.0068(3) -0.0231(9) 0.0231(11) Uani 1 1 d . . . . .
C1 C 0.5869(10) 0.1112(2) 0.4973(10) 0.0140(11) Uani 1 1 d . . . . .
H1 H 0.632(12) 0.096(3) 0.620(13) 0.017 Uiso 1 1 d . U . . .
C2 C 0.4793(10) 0.1605(2) 0.5112(10) 0.0147(10) Uani 1 1 d . . . . .
H2 H 0.555(12) 0.176(2) 0.680(12) 0.018 Uiso 1 1 d . U . . .
C3 C 0.3044(10) 0.1825(2) 0.2962(11) 0.0181(11) Uani 1 1 d . . . . .
H3 H 0.242(11) 0.216(2) 0.302(11) 0.012(14) Uiso 1 1 d . . . . .
C4 C 0.2014(10) 0.1603(2) 0.0360(10) 0.0180(11) Uani 1 1 d . . . . .
H4A H 0.218(13) 0.178(3) -0.076(12) 0.018(16) Uiso 1 1 d . . . . .
H4B H -0.004(16) 0.154(3) -0.038(13) 0.04(2) Uiso 1 1 d . . . . .
C5 C 0.3561(9) 0.1139(2) 0.0495(10) 0.0155(11) Uani 1 1 d . . . . .
H5 H 0.282(12) 0.100(2) -0.126(12) 0.019 Uiso 1 1 d . U . . .
C6 C 0.3792(9) 0.08451(19) 0.2708(9) 0.0131(10) Uani 1 1 d . . . . .
C7 C 0.7832(10) 0.1174(2) 0.3953(10) 0.0166(10) Uani 1 1 d . . . . .
H7A H 0.895(12) 0.143(3) 0.457(11) 0.012(14) Uiso 1 1 d . . . . .
H7B H 0.874(15) 0.082(3) 0.420(14) 0.04(2) Uiso 1 1 d . . . . .
C8 C 0.2626(9) 0.04325(19) 0.2728(9) 0.0131(10) Uani 1 1 d . . . . .
H8 H 0.264(18) 0.021(4) 0.400(17) 0.06(3) Uiso 1 1 d . . . . .
C9 C -0.2223(11) 0.0092(2) -0.0104(9) 0.0169(11) Uani 1 1 d . . . . .
S11 S 0.8311(2) 0.42536(5) 0.5021(2) 0.0144(4) Uani 1 1 d . . . . .
O11 O 1.2300(7) 0.30912(14) 0.3378(6) 0.0154(8) Uani 1 1 d . . . . .
N11 N 0.3425(9) 0.4296(3) 0.4959(9) 0.0233(12) Uani 1 1 d . . . . .
C11 C 0.8276(9) 0.3274(2) -0.0300(9) 0.0128(10) Uani 1 1 d . . . . .
H11 H 0.747(12) 0.347(3) -0.179(13) 0.021(16) Uiso 1 1 d . . . . .
C12 C 0.6980(10) 0.2786(2) -0.0494(11) 0.0166(11) Uani 1 1 d . . . . .
H12 H 0.597(13) 0.267(3) -0.214(14) 0.020(16) Uiso 1 1 d . . . . .
C13 C 0.7347(11) 0.2556(2) 0.1611(11) 0.0164(11) Uani 1 1 d . . . . .
H13 H 0.66(2) 0.224(4) 0.132(19) 0.07(3) Uiso 1 1 d . . . . .
C14 C 0.9006(12) 0.2772(2) 0.4283(11) 0.0183(11) Uani 1 1 d . . . . .
H14A H 1.029(14) 0.255(3) 0.546(13) 0.022(17) Uiso 1 1 d . . . . .
H14B H 0.804(13) 0.287(3) 0.486(12) 0.017(17) Uiso 1 1 d . . . . .
C15 C 1.0420(10) 0.3228(2) 0.4172(9) 0.0132(10) Uani 1 1 d . . . . .
H15 H 1.139(11) 0.342(2) 0.577(12) 0.016 Uiso 1 1 d . U . . .
C16 C 0.8493(9) 0.35394(19) 0.2015(9) 0.0129(10) Uani 1 1 d . . . . .
C17 C 1.1221(10) 0.3202(2) 0.0663(10) 0.0160(10) Uani 1 1 d . . . . .
H17A H 1.147(12) 0.287(3) -0.007(12) 0.019 Uiso 1 1 d . U . . .
H17B H 1.212(14) 0.350(3) 0.032(13) 0.027(18) Uiso 1 1 d . . . . .
C18 C 0.7355(10) 0.39529(19) 0.2041(9) 0.0129(10) Uani 1 1 d . . . . .
H18 H 0.634(12) 0.414(3) 0.049(12) 0.016 Uiso 1 1 d . U . . .
C19 C 0.5352(11) 0.4268(2) 0.4909(9) 0.0162(11) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 C9 1.699(6) . ?
S1 C8 1.785(5) . ?
O1 C7 1.437(6) . ?
O1 C5 1.439(6) . ?
N1 C9 1.155(8) . ?
C1 C6 1.495(7) . ?
C1 C2 1.516(8) . ?
C1 C7 1.553(7) . ?
C1 H1 0.77(7) . ?
C2 C3 1.332(8) . ?
C2 H2 0.98(6) . ?
C3 C4 1.494(8) . ?
C3 H3 0.99(7) . ?
C4 C5 1.546(8) . ?
C4 H4A 0.87(7) . ?
C4 H4B 1.08(8) . ?
C5 C6 1.497(7) . ?
C5 H5 0.99(6) . ?
C6 C8 1.329(7) . ?
C7 H7A 0.92(7) . ?
C7 H7B 1.08(9) . ?
C8 H8 0.97(10) . ?
S11 C19 1.703(6) . ?
S11 C18 1.785(5) . ?
O11 C15 1.447(6) . ?
O11 C17 1.454(6) . ?
N11 C19 1.147(8) . ?
C11 C16 1.512(7) . ?
C11 C12 1.519(7) . ?
C11 C17 1.542(7) . ?
C11 H11 0.95(7) . ?
C12 C13 1.327(8) . ?
C12 H12 0.92(7) . ?
C13 C14 1.524(8) . ?
C13 H13 0.95(11) . ?
C14 C15 1.523(7) . ?
C14 H14A 0.96(8) . ?
C14 H14B 0.83(7) . ?
C15 C16 1.498(7) . ?
C15 H15 0.98(6) . ?
C16 C18 1.324(8) . ?
C17 H17A 1.05(8) . ?
C17 H17B 1.06(8) . ?
C18 H18 0.97(7) . ?

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
C9 S1 C8 99.8(2) . . ?
C7 O1 C5 108.8(4) . . ?
C6 C1 C2 108.2(4) . . ?
C6 C1 C7 97.5(4) . . ?
C2 C1 C7 109.3(4) . . ?
C6 C1 H1 110(5) . . ?
C2 C1 H1 113(5) . . ?
C7 C1 H1 117(5) . . ?
C3 C2 C1 120.0(5) . . ?
C3 C2 H2 122(4) . . ?
C1 C2 H2 118(4) . . ?
C2 C3 C4 122.9(5) . . ?
C2 C3 H3 121(3) . . ?
C4 C3 H3 116(3) . . ?
C3 C4 C5 110.9(4) . . ?
C3 C4 H4A 116(4) . . ?
C5 C4 H4A 102(4) . . ?
C3 C4 H4B 107(4) . . ?
C5 C4 H4B 114(5) . . ?
H4A C4 H4B 107(6) . . ?
O1 C5 C6 104.0(4) . . ?
O1 C5 C4 108.8(4) . . ?
C6 C5 C4 106.9(4) . . ?
O1 C5 H5 106(4) . . ?
C6 C5 H5 122(4) . . ?
C4 C5 H5 108(4) . . ?
C8 C6 C1 127.3(5) . . ?
C8 C6 C5 130.2(5) . . ?
C1 C6 C5 102.3(4) . . ?
O1 C7 C1 104.5(4) . . ?
O1 C7 H7A 105(4) . . ?
C1 C7 H7A 117(4) . . ?
O1 C7 H7B 109(4) . . ?
C1 C7 H7B 105(4) . . ?
H7A C7 H7B 116(5) . . ?
C6 C8 S1 121.5(4) . . ?
C6 C8 H8 137(6) . . ?
S1 C8 H8 101(5) . . ?
N1 C9 S1 175.2(5) . . ?
C19 S11 C18 98.9(2) . . ?
C15 O11 C17 109.0(4) . . ?
C16 C11 C12 108.2(4) . . ?
C16 C11 C17 98.3(4) . . ?
C12 C11 C17 110.0(4) . . ?
C16 C11 H11 111(4) . . ?
C12 C11 H11 116(4) . . ?
C17 C11 H11 112(4) . . ?
C13 C12 C11 120.5(5) . . ?
C13 C12 H12 124(4) . . ?
C11 C12 H12 116(4) . . ?
C12 C13 C14 121.8(5) . . ?
C12 C13 H13 115(6) . . ?
C14 C13 H13 123(6) . . ?
C15 C14 C13 111.0(4) . . ?
C15 C14 H14A 108(4) . . ?
C13 C14 H14A 113(4) . . ?
C15 C14 H14B 105(5) . . ?
C13 C14 H14B 110(4) . . ?
H14A C14 H14B 110(6) . . ?
O11 C15 C16 104.0(4) . . ?
O11 C15 C14 108.5(4) . . ?
C16 C15 C14 108.2(4) . . ?
O11 C15 H15 107(3) . . ?
C16 C15 H15 111(4) . . ?
C14 C15 H15 117(4) . . ?
C18 C16 C15 130.9(5) . . ?
C18 C16 C11 127.6(5) . . ?
C15 C16 C11 101.4(4) . . ?
O11 C17 C11 103.8(4) . . ?
O11 C17 H17A 102(4) . . ?
C11 C17 H17A 108(3) . . ?
O11 C17 H17B 113(4) . . ?
C11 C17 H17B 114(4) . . ?
H17A C17 H17B 115(5) . . ?
C16 C18 S11 119.8(4) . . ?
C16 C18 H18 122(4) . . ?
S11 C18 H18 117(4) . . ?
N11 C19 S11 175.9(5) . . ?

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
C6 C1 C2 C3 -31.1(6) . . . . ?
C7 C1 C2 C3 74.1(6) . . . . ?
C1 C2 C3 C4 1.4(8) . . . . ?
C2 C3 C4 C5 -9.2(8) . . . . ?
C7 O1 C5 C6 -13.4(5) . . . . ?
C7 O1 C5 C4 100.2(5) . . . . ?
C3 C4 C5 O1 -65.2(5) . . . . ?
C3 C4 C5 C6 46.6(6) . . . . ?
C2 C1 C6 C8 -117.3(6) . . . . ?
C7 C1 C6 C8 129.5(5) . . . . ?
C2 C1 C6 C5 67.0(5) . . . . ?
C7 C1 C6 C5 -46.3(5) . . . . ?
O1 C5 C6 C8 -136.8(5) . . . . ?
C4 C5 C6 C8 108.3(6) . . . . ?
O1 C5 C6 C1 38.8(5) . . . . ?
C4 C5 C6 C1 -76.1(5) . . . . ?
C5 O1 C7 C1 -16.1(5) . . . . ?
C6 C1 C7 O1 38.6(5) . . . . ?
C2 C1 C7 O1 -73.8(5) . . . . ?
C1 C6 C8 S1 -167.8(4) . . . . ?
C5 C6 C8 S1 6.8(8) . . . . ?
C9 S1 C8 C6 -121.8(5) . . . . ?
C16 C11 C12 C13 -32.1(6) . . . . ?
C17 C11 C12 C13 74.3(6) . . . . ?
C11 C12 C13 C14 1.5(8) . . . . ?
C12 C13 C14 C15 -8.3(8) . . . . ?
C17 O11 C15 C16 -14.1(5) . . . . ?
C17 O11 C15 C14 100.9(5) . . . . ?
C13 C14 C15 O11 -65.9(6) . . . . ?
C13 C14 C15 C16 46.3(6) . . . . ?
O11 C15 C16 C18 -137.3(5) . . . . ?
C14 C15 C16 C18 107.5(6) . . . . ?
O11 C15 C16 C11 39.2(5) . . . . ?
C14 C15 C16 C11 -76.0(5) . . . . ?
C12 C11 C16 C18 -116.4(6) . . . . ?
C17 C11 C16 C18 129.2(5) . . . . ?
C12 C11 C16 C15 67.0(5) . . . . ?
C17 C11 C16 C15 -47.4(5) . . . . ?
C15 O11 C17 C11 -16.2(5) . . . . ?
C16 C11 C17 O11 39.1(5) . . . . ?
C12 C11 C17 O11 -73.8(5) . . . . ?
C15 C16 C18 S11 6.1(8) . . . . ?
C11 C16 C18 S11 -169.5(4) . . . . ?
C19 S11 C18 C16 -121.8(4) . . . . ?

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
C8 H8 S11 0.97(10) 2.82(10) 3.656(5) 145(7) 2_646

_refine_diff_density_max         0.573
_refine_diff_density_min         -0.528
_refine_diff_density_rms         0.097

_shelxl_version_number           2013-4

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_14066
_database_code_depnum_ccdc_archive 'CCDC 1513687'
_audit_update_record             
;
2016-10-31 deposited with the CCDC.
2017-10-02 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C15 H16 N2 O2 S2'
_chemical_formula_sum            'C15 H16 N2 O2 S2'
_chemical_formula_weight         320.42

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_shelx_space_group_comment       
; 
The symmetry employed for this shelxl refinement is uniquely defined 
by the following loop, which should always be used as a source of 
symmetry information in preference to the above space-group names. 
They are only intended as comments. 
;

loop_
_space_group_symop_operation_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                   16.354(6)
_cell_length_b                   5.370(2)
_cell_length_c                   17.896(7)
_cell_angle_alpha                90
_cell_angle_beta                 92.655(8)
_cell_angle_gamma                90
_cell_volume                     1570.0(10)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    1133
_cell_measurement_theta_min      2.28
_cell_measurement_theta_max      24.51

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.356
_exptl_crystal_F_000             672
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.540
_exptl_crystal_size_mid          0.050
_exptl_crystal_size_min          0.020
_exptl_absorpt_coefficient_mu    0.344
_shelx_estimated_absorpt_T_min   0.836
_shelx_estimated_absorpt_T_max   0.993
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.836
_exptl_absorpt_correction_T_max  0.993
_exptl_absorpt_process_details   'SADABS (Bruker, 2002)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'CCD Bruker APEX'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            28257
_diffrn_reflns_av_unetI/netI     0.0578
_diffrn_reflns_av_R_equivalents  0.0821
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         1.649
_diffrn_reflns_theta_max         28.462
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             3925
_reflns_number_gt                2650
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
; 
 Reflections were merged by SHELXL according to the crystal 
 class for the calculation of statistics and refinement. 
  
 _reflns_Friedel_fraction is defined as the number of unique 
 Friedel pairs measured divided by the number that would be 
 possible theoretically, ignoring centric projections and 
 systematic absences. 
;

_computing_data_collection       'APEX2 (Bruker, 2007)'
_computing_cell_refinement       'SAINT (Bruker, 2007)'
_computing_data_reduction        'SAINT (Bruker, 2007)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    'XP (Bruker, 2002)'
_computing_publication_material  'SHELXL-2014 (Sheldrick, 2014)'

_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)+(0.0650P)²+2.5000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3925
_refine_ls_number_parameters     209
_refine_ls_number_restraints     15
_refine_ls_R_factor_all          0.1010
_refine_ls_R_factor_gt           0.0616
_refine_ls_wR_factor_ref         0.1608
_refine_ls_wR_factor_gt          0.1407
_refine_ls_goodness_of_fit_ref   0.998
_refine_ls_restrained_S_all      0.999
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.42050(5) 1.09598(14) 0.30331(4) 0.02657(19) Uani 1 1 d . . . . .
S2 S 0.38761(6) 0.4167(2) 0.06538(6) 0.0520(3) Uani 1 1 d . . . . .
O1 O 0.35084(14) 1.1913(4) 0.26107(12) 0.0349(5) Uani 1 1 d . . . . .
O2 O 0.47732(13) 1.2622(4) 0.34092(12) 0.0328(5) Uani 1 1 d . . . . .
N1 N 0.47345(15) 0.9384(5) 0.24494(13) 0.0278(6) Uani 1 1 d . . . . .
N2 N 0.3992(2) -0.0097(7) -0.0237(2) 0.0563(9) Uani 1 1 d . . . . .
C1 C 0.38617(17) 0.8820(5) 0.36935(15) 0.0238(6) Uani 1 1 d . . . . .
C2 C 0.31420(17) 0.7482(6) 0.35541(16) 0.0275(6) Uani 1 1 d . . . . .
H2 H 0.2809 0.7788 0.3115 0.033 Uiso 1 1 calc R U . . .
C3 C 0.29192(18) 0.5704(6) 0.40640(18) 0.0323(7) Uani 1 1 d . . . . .
H3 H 0.2438 0.4750 0.3962 0.039 Uiso 1 1 calc R U . . .
C4 C 0.33816(18) 0.5274(6) 0.47242(17) 0.0300(7) Uani 1 1 d . . . . .
C5 C 0.40954(18) 0.6655(6) 0.48584(17) 0.0296(7) Uani 1 1 d . . . . .
H5 H 0.4417 0.6405 0.5308 0.035 Uiso 1 1 calc R U . . .
C6 C 0.43397(18) 0.8390(6) 0.43407(16) 0.0263(6) Uani 1 1 d . . . . .
H6 H 0.4836 0.9287 0.4429 0.032 Uiso 1 1 calc R U . . .
C7 C 0.3125(2) 0.3328(7) 0.5273(2) 0.0417(8) Uani 1 1 d . . . . .
H7A H 0.2541 0.3516 0.5359 0.063 Uiso 1 1 d R U . . .
H7B H 0.3442 0.3536 0.5747 0.063 Uiso 1 1 d R U . . .
H7C H 0.3226 0.1667 0.5070 0.063 Uiso 1 1 d R U . . .
C8 C 0.42911(19) 0.7693(6) 0.19251(17) 0.0315(7) Uani 1 1 d . . . . .
H8A H 0.3987 0.8632 0.1526 0.038 Uiso 1 1 calc R U . . .
H8B H 0.3904 0.6621 0.2188 0.038 Uiso 1 1 calc R U . . .
C9 C 0.49696(19) 0.6187(6) 0.16140(17) 0.0326(7) Uani 1 1 d . . . . .
C10 C 0.5774(2) 0.6889(8) 0.2011(2) 0.0463(9) Uani 1 1 d D U . . .
H10_a H 0.6025 0.8220 0.1705 0.056 Uiso 0.804(7) 1 d R U P A 1
H10'_b H 0.5892 0.5217 0.2240 0.056 Uiso 0.196(7) 1 d R U P A 2
C11 C 0.54928(18) 0.8129(6) 0.27214(17) 0.0307(7) Uani 1 1 d . . . . .
H11A H 0.5383 0.6883 0.3112 0.037 Uiso 1 1 calc R U . . .
H11B H 0.5903 0.9340 0.2922 0.037 Uiso 1 1 calc R U . . .
C12 C 0.48691(19) 0.4506(6) 0.10727(18) 0.0341(7) Uani 1 1 d . . . . .
H12 H 0.5314 0.3525 0.0917 0.041 Uiso 1 1 calc R U . . .
C13 C 0.3977(2) 0.1626(6) 0.01395(17) 0.0335(7) Uani 1 1 d . . . . .
C14_a C 0.6369(2) 0.4940(8) 0.2098(2) 0.0398(12) Uani 0.804(7) 1 d D U P A 1
H14_a H 0.6232 0.3591 0.2412 0.048 Uiso 0.804(7) 1 calc R U P A 1
C15_a C 0.7083(3) 0.4809(12) 0.1792(3) 0.0509(15) Uani 0.804(7) 1 d D U P A 1
H15A_a H 0.7252 0.6105 0.1473 0.061 Uiso 0.804(7) 1 calc R U P A 1
H15B_a H 0.7430 0.3417 0.1890 0.061 Uiso 0.804(7) 1 calc R U P A 1
C14'_b C 0.6530(5) 0.736(3) 0.1678(8) 0.035(4) Uani 0.196(7) 1 d D U P A 2
H14'_b H 0.6594 0.9008 0.1496 0.042 Uiso 0.196(7) 1 calc R U P A 2
C15'_b C 0.7153(8) 0.588(4) 0.1583(12) 0.039(4) Uani 0.196(7) 1 d D U P A 2
H15C_b H 0.7136 0.4202 0.1750 0.047 Uiso 0.196(7) 1 calc R U P A 2
H15D_b H 0.7622 0.6483 0.1347 0.047 Uiso 0.196(7) 1 calc R U P A 2


_geom_special_details            
; 
;

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 O1 1.432(2) . ?
S1 O2 1.434(2) . ?
S1 N1 1.625(3) . ?
S1 C1 1.759(3) . ?
S2 C13 1.659(4) . ?
S2 C12 1.766(3) . ?
N1 C8 1.472(4) . ?
N1 C11 1.474(4) . ?
N2 C13 1.145(4) . ?
C1 C6 1.386(4) . ?
C1 C2 1.391(4) . ?
C2 C3 1.381(4) . ?
C2 H2 0.9500 . ?
C3 C4 1.392(4) . ?
C3 H3 0.9500 . ?
C4 C5 1.395(4) . ?
C4 C7 1.507(5) . ?
C5 C6 1.386(4) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C8 C9 1.501(4) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 C12 1.329(4) . ?
C9 C10 1.513(4) . ?
C10 C14'_b 1.420(6) . ?
C10 C14_a 1.432(5) . ?
C10 C11 1.524(4) . ?
C10 H10_a 1.0012 . ?
C10 H10'_b 1.0015 . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 H12 0.9500 . ?
C14_a C15_a 1.315(6) . ?
C14_a H14_a 0.9500 . ?
C15_a H15A_a 0.9500 . ?
C15_a H15B_a 0.9500 . ?
C14'_b C15'_b 1.310(7) . ?
C14'_b H14'_b 0.9500 . ?
C15'_b H15C_b 0.9500 . ?
C15'_b H15D_b 0.9500 . ?

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 S1 O2 120.51(14) . . ?
O1 S1 N1 106.34(13) . . ?
O2 S1 N1 105.83(13) . . ?
O1 S1 C1 108.49(14) . . ?
O2 S1 C1 108.15(13) . . ?
N1 S1 C1 106.74(13) . . ?
C13 S2 C12 101.94(16) . . ?
C8 N1 C11 108.1(2) . . ?
C8 N1 S1 118.0(2) . . ?
C11 N1 S1 119.41(19) . . ?
C6 C1 C2 120.2(3) . . ?
C6 C1 S1 119.0(2) . . ?
C2 C1 S1 120.7(2) . . ?
C3 C2 C1 119.0(3) . . ?
C3 C2 H2 120.5 . . ?
C1 C2 H2 120.5 . . ?
C2 C3 C4 121.7(3) . . ?
C2 C3 H3 119.1 . . ?
C4 C3 H3 119.1 . . ?
C3 C4 C5 118.4(3) . . ?
C3 C4 C7 120.8(3) . . ?
C5 C4 C7 120.8(3) . . ?
C6 C5 C4 120.5(3) . . ?
C6 C5 H5 119.7 . . ?
C4 C5 H5 119.8 . . ?
C5 C6 C1 120.1(3) . . ?
C5 C6 H6 120.0 . . ?
C1 C6 H6 120.0 . . ?
C4 C7 H7A 109.5 . . ?
C4 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C4 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
N1 C8 C9 102.6(2) . . ?
N1 C8 H8A 111.2 . . ?
C9 C8 H8A 111.2 . . ?
N1 C8 H8B 111.2 . . ?
C9 C8 H8B 111.2 . . ?
H8A C8 H8B 109.2 . . ?
C12 C9 C8 124.6(3) . . ?
C12 C9 C10 126.0(3) . . ?
C8 C9 C10 109.4(3) . . ?
C14'_b C10 C9 127.0(7) . . ?
C14_a C10 C9 116.1(3) . . ?
C14'_b C10 C11 125.0(7) . . ?
C14_a C10 C11 117.3(3) . . ?
C9 C10 C11 102.2(3) . . ?
C14_a C10 H10_a 106.7 . . ?
C9 C10 H10_a 106.9 . . ?
C11 C10 H10_a 107.0 . . ?
C14'_b C10 H10'_b 100.2 . . ?
C9 C10 H10'_b 96.6 . . ?
C11 C10 H10'_b 96.4 . . ?
N1 C11 C10 101.9(2) . . ?
N1 C11 H11A 111.4 . . ?
C10 C11 H11A 111.4 . . ?
N1 C11 H11B 111.4 . . ?
C10 C11 H11B 111.4 . . ?
H11A C11 H11B 109.3 . . ?
C9 C12 S2 117.4(3) . . ?
C9 C12 H12 121.3 . . ?
S2 C12 H12 121.3 . . ?
N2 C13 S2 175.1(3) . . ?
C15_a C14_a C10 127.3(5) . . ?
C15_a C14_a H14_a 116.3 . . ?
C10 C14_a H14_a 116.3 . . ?
C14_a C15_a H15A_a 120.0 . . ?
C14_a C15_a H15B_a 120.0 . . ?
H15A_a C15_a H15B_a 120.0 . . ?
C15'_b C14'_b C10 130.1(9) . . ?
C15'_b C14'_b H14'_b 115.0 . . ?
C10 C14'_b H14'_b 115.0 . . ?
C14'_b C15'_b H15C_b 120.0 . . ?
C14'_b C15'_b H15D_b 120.0 . . ?
H15C_b C15'_b H15D_b 120.0 . . ?

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
O1 S1 N1 C8 -44.5(3) . . . . ?
O2 S1 N1 C8 -173.8(2) . . . . ?
C1 S1 N1 C8 71.2(2) . . . . ?
O1 S1 N1 C11 -179.2(2) . . . . ?
O2 S1 N1 C11 51.5(3) . . . . ?
C1 S1 N1 C11 -63.5(2) . . . . ?
O1 S1 C1 C6 -154.8(2) . . . . ?
O2 S1 C1 C6 -22.5(3) . . . . ?
N1 S1 C1 C6 91.0(2) . . . . ?
O1 S1 C1 C2 28.4(3) . . . . ?
O2 S1 C1 C2 160.7(2) . . . . ?
N1 S1 C1 C2 -85.9(3) . . . . ?
C6 C1 C2 C3 -0.9(4) . . . . ?
S1 C1 C2 C3 175.9(2) . . . . ?
C1 C2 C3 C4 2.1(5) . . . . ?
C2 C3 C4 C5 -1.3(5) . . . . ?
C2 C3 C4 C7 179.9(3) . . . . ?
C3 C4 C5 C6 -0.7(4) . . . . ?
C7 C4 C5 C6 178.1(3) . . . . ?
C4 C5 C6 C1 1.9(4) . . . . ?
C2 C1 C6 C5 -1.1(4) . . . . ?
S1 C1 C6 C5 -177.9(2) . . . . ?
C11 N1 C8 C9 -28.3(3) . . . . ?
S1 N1 C8 C9 -167.7(2) . . . . ?
N1 C8 C9 C12 -175.2(3) . . . . ?
N1 C8 C9 C10 4.8(4) . . . . ?
C12 C9 C10 C14'_b 45.0(9) . . . . ?
C8 C9 C10 C14'_b -135.0(8) . . . . ?
C12 C9 C10 C14_a -32.2(6) . . . . ?
C8 C9 C10 C14_a 147.9(3) . . . . ?
C12 C9 C10 C11 -161.1(3) . . . . ?
C8 C9 C10 C11 19.0(4) . . . . ?
C8 N1 C11 C10 40.6(3) . . . . ?
S1 N1 C11 C10 179.3(2) . . . . ?
C14'_b C10 C11 N1 119.7(7) . . . . ?
C14_a C10 C11 N1 -163.1(3) . . . . ?
C9 C10 C11 N1 -34.9(3) . . . . ?
C8 C9 C12 S2 4.0(5) . . . . ?
C10 C9 C12 S2 -175.9(3) . . . . ?
C13 S2 C12 C9 -170.2(3) . . . . ?
C14'_b C10 C14_a C15_a -6.4(9) . . . . ?
C9 C10 C14_a C15_a 114.3(5) . . . . ?
C11 C10 C14_a C15_a -124.6(5) . . . . ?
C14_a C10 C14'_b C15'_b 8.8(18) . . . . ?
C9 C10 C14'_b C15'_b -96(2) . . . . ?
C11 C10 C14'_b C15'_b 116(2) . . . . ?

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
C2 H2 O1 0.95 2.51 3.347(4) 147.4 2_545
C11 H11A O2 0.99 2.56 3.432(4) 146.7 1_545
C12 H12 N2 0.95 2.51 3.401(5) 156.8 3_655

_refine_diff_density_max         0.513
_refine_diff_density_min         -0.588
_refine_diff_density_rms         0.073

_shelxl_version_number           2014-1

_iucr_refine_instruction_details 
; 
TITL 14066 in P2(1)/n 
CELL 0.71073  16.354   5.370  17.896  90.0000  92.655  90.0000 
ZERR    4.00   0.006   0.002   0.007   0.0000   0.008   0.0000 
LATT  1 
SYMM 0.5-X, 0.5+Y, 0.5-Z 
SFAC C  H  N O S 
UNIT 60 64 8 8 8 
TEMP -173.170 
SIZE 0.02 0.05 0.54 
ACTA 
CONF 
WPDB -1 
EQIV $1 -x+1/2, y-1/2, -z+1/2 
HTAB C2 O1_$1 
EQIV $2 x, y-1, z 
HTAB C11 O2_$2 
EQIV $3 -x+1, -y, -z 
HTAB C12 N2_$3 
HTAB 
  
L.S. 8 4 
BOND $H 
FMAP 2 
PLAN 20 
sadi 0.004 c10 c14 c10 c14' 
sadi 0.004 c14 c15 c14' c15' 
sadi 0.008 c10 c15 c10 c15' 
delu 0.004 c10 c14 c15 c14' c15' 
isor 0.004 c15' 
  
WGHT    0.065000    2.500000 
FVAR       0.66863   0.80398 
S1    5    0.420500    1.095982    0.303309    11.00000    0.03304    0.02085 = 
         0.02518   -0.00342   -0.00553    0.00229 
S2    5    0.387613    0.416750    0.065383    11.00000    0.04226    0.05426 = 
         0.05781   -0.02981   -0.01454    0.00672 
O1    4    0.350837    1.191317    0.261075    11.00000    0.04227    0.02783 = 
         0.03341   -0.00312   -0.01067    0.00629 
O2    4    0.477319    1.262177    0.340916    11.00000    0.04056    0.02284 = 
         0.03427   -0.00535   -0.00451   -0.00312 
N1    3    0.473453    0.938439    0.244939    11.00000    0.03395    0.02690 = 
         0.02236   -0.00314   -0.00209   -0.00235 
N2    3    0.399219   -0.009673   -0.023699    11.00000    0.04695    0.05943 = 
         0.06342   -0.02929    0.01100   -0.01516 
C1    1    0.386166    0.881987    0.369347    11.00000    0.02600    0.02159 = 
         0.02343   -0.00754   -0.00276    0.00389 
C2    1    0.314196    0.748240    0.355407    11.00000    0.02204    0.03475 = 
         0.02511   -0.00315   -0.00408    0.00633 
AFIX  43 
H2    2    0.280875    0.778760    0.311466    11.00000   -1.20000 
AFIX   0 
C3    1    0.291917    0.570444    0.406400    11.00000    0.02077    0.03865 = 
         0.03742   -0.00275    0.00191    0.00081 
AFIX  43 
H3    2    0.243776    0.475044    0.396155    11.00000   -1.20000 
AFIX   0 
C4    1    0.338160    0.527368    0.472421    11.00000    0.02867    0.03069 = 
         0.03098    0.00121    0.00623    0.00763 
C5    1    0.409536    0.665517    0.485843    11.00000    0.02860    0.03415 = 
         0.02571   -0.00173   -0.00164    0.01055 
AFIX  43 
H5    2    0.441652    0.640495    0.530815    11.00000   -1.20000 
AFIX   0 
C6    1    0.433973    0.839037    0.434073    11.00000    0.02624    0.02883 = 
         0.02355   -0.00557   -0.00301    0.00182 
AFIX  43 
H6    2    0.483554    0.928683    0.442947    11.00000   -1.20000 
AFIX   0 
C7    1    0.312529    0.332794    0.527294    11.00000    0.03763    0.04158 = 
         0.04688    0.01128    0.01118    0.00896 
AFIX   3 
H7A   2    0.254097    0.351569    0.535858    11.00000   -1.50000 
H7B   2    0.344225    0.353598    0.574708    11.00000   -1.50000 
H7C   2    0.322595    0.166653    0.507009    11.00000   -1.50000 
AFIX   0 
C8    1    0.429114    0.769334    0.192510    11.00000    0.03385    0.03473 = 
         0.02552   -0.00698   -0.00386   -0.00091 
AFIX  23 
H8A   2    0.398668    0.863223    0.152567    11.00000   -1.20000 
H8B   2    0.390442    0.662148    0.218794    11.00000   -1.20000 
AFIX   0 
C9    1    0.496964    0.618694    0.161401    11.00000    0.02993    0.04043 = 
         0.02773   -0.00722    0.00582   -0.00432 
C10   1    0.577380    0.688876    0.201130    11.00000    0.02995    0.06376 = 
         0.04522   -0.02599    0.00296   -0.00148 
part   1 
AFIX   3 
H10   2    0.602547    0.822015    0.170479    21.00000   -1.20000 
AFIX   3 
PART   2 
H10'  2    0.589160    0.521706    0.223980   -21.00000   -1.20000 
AFIX   0 
PART   0 
C11   1    0.549280    0.812887    0.272138    11.00000    0.02673    0.03356 = 
         0.03166   -0.00939   -0.00018   -0.00166 
AFIX  23 
H11A  2    0.538289    0.688270    0.311186    11.00000   -1.20000 
H11B  2    0.590287    0.934038    0.292242    11.00000   -1.20000 
AFIX   0 
C12   1    0.486911    0.450618    0.107267    11.00000    0.03112    0.03987 = 
         0.03145   -0.00993    0.00222   -0.00210 
AFIX  43 
H12   2    0.531377    0.352541    0.091707    11.00000   -1.20000 
AFIX   0 
C13   1    0.397730    0.162564    0.013950    11.00000    0.03445    0.04076 = 
         0.02559   -0.00231    0.00468   -0.01016 
PART   1 
C14   1    0.636852    0.494025    0.209813    21.00000    0.03440    0.03895 = 
         0.04594   -0.01650    0.00108   -0.00425 
AFIX  43 
H14   2    0.623165    0.359134    0.241226    21.00000   -1.20000 
AFIX   0 
C15   1    0.708269    0.480860    0.179191    21.00000    0.03968    0.06046 = 
         0.05269   -0.00586    0.00282    0.01475 
AFIX  93 
H15A  2    0.725163    0.610547    0.147260    21.00000   -1.20000 
H15B  2    0.742977    0.341659    0.188996    21.00000   -1.20000 
AFIX   0 
PART   2 
C14'  1    0.652981    0.736104    0.167829   -21.00000    0.02948    0.04500 = 
         0.03075   -0.00016   -0.00451    0.00519 
AFIX  43 
H14'  2    0.659376    0.900815    0.149630   -21.00000   -1.20000 
AFIX   0 
C15'  1    0.715292    0.587957    0.158284   -21.00000    0.03578    0.04439 = 
         0.03929   -0.00785    0.01324    0.00242 
AFIX  93 
H15C  2    0.713560    0.420209    0.174998   -21.00000   -1.20000 
H15D  2    0.762204    0.648286    0.134651   -21.00000   -1.20000 
PART   0 
  
AFIX   0 
HKLF 4 
  
REM  14066 in P2(1)/n 
REM R1 =  0.0616 for    2650 Fo > 4sig(Fo)  and  0.1010 for all    3925 data 
REM    209 parameters refined using     15 restraints 
  
END 
  
WGHT      0.0516      2.4585 
  
REM Instructions for potential hydrogen bonds 
HTAB C2 O1_$1 
HTAB C11 O2_$2 
HTAB C12 N2_$3 
  
REM Highest difference peak  0.513,  deepest hole -0.588,  1-sigma level  0.073 
Q1    1   0.6384  0.6921  0.1762  11.00000  0.05    0.51 
Q2    1   0.6623  0.3719  0.2354  11.00000  0.05    0.45 
Q3    1   0.4132  0.8416  0.3974  11.00000  0.05    0.42 
Q4    1   0.4343  0.4095  0.0987  11.00000  0.05    0.40 
Q5    1   0.3931  0.3001  0.0984  11.00000  0.05    0.36 
Q6    1   0.3648  0.7786  0.3647  11.00000  0.05    0.30 
Q7    1   0.3895  1.1065  0.2618  11.00000  0.05    0.29 
Q8    1   0.4394  0.6199  0.1363  11.00000  0.05    0.28 
Q9    1   0.5352  0.6693  0.1785  11.00000  0.05    0.27 
Q10   1   0.4415  0.4669  0.0639  11.00000  0.05    0.27 
Q11   1   0.3044  0.5752  0.4457  11.00000  0.05    0.27 
Q12   1   0.3540  0.4261  0.0199  11.00000  0.05    0.27 
Q13   1   0.3105  1.1512  0.2894  11.00000  0.05    0.26 
Q14   1   0.5386  0.5461  0.1822  11.00000  0.05    0.26 
Q15   1   0.5724  0.4367  0.1647  11.00000  0.05    0.26 
Q16   1   0.3791  0.5648  0.4818  11.00000  0.05    0.25 
Q17   1   0.3794  1.1758  0.2821  11.00000  0.05    0.25 
Q18   1   0.4980  0.4712  0.1595  11.00000  0.05    0.25 
Q19   1   0.3861  1.0192  0.3352  11.00000  0.05    0.25 
Q20   1   0.5034  0.8397  0.2577  11.00000  0.05    0.24 
;
