# Electronic Supplementary Material (ESI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 2016

####################################################################### 
# 
# 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_vi991_0m
_database_code_depnum_ccdc_archive 'CCDC 1480993'
_audit_update_record             
;
2016-05-19 deposited with the CCDC.
2016-07-28 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C12 H16 N2 O4 S'
_chemical_formula_sum            'C12 H16 N2 O4 S'
_chemical_formula_weight         284.33
_chemical_absolute_configuration ad

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'

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   P212121
_symmetry_space_group_name_Hall  'P 2ac 2ab '

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

_cell_length_a                   5.7221(1)
_cell_length_b                   9.3754(2)
_cell_length_c                   24.6691(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1323.42(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    5741
_cell_measurement_theta_min      3.55
_cell_measurement_theta_max      66.8

_exptl_crystal_description       plate-like
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.05
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.427
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             600
_exptl_absorpt_coefficient_mu    2.304
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5449
_exptl_absorpt_correction_T_max  0.8935
_exptl_absorpt_process_details   'SADABS; (Sheldrick, 2003)'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'BRUKER SMART APEXII CCD'
_diffrn_measurement_method       'omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            11376
_diffrn_reflns_av_R_equivalents  0.0405
_diffrn_reflns_av_sigmaI/netI    0.0311
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_theta_min         3.58
_diffrn_reflns_theta_max         67.34
_reflns_number_total             2324
_reflns_number_gt                2232
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'APEX2 (Bruker, 2010)'
_computing_cell_refinement       'APEX2 (Bruker, 2010); SAINT (Bruker, 2009)'
_computing_data_reduction        'SAINT (Bruker, 2009);XPREP(Sheldrick,2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    ?
_computing_publication_material  'APEX2 (Bruker, 2010)'
_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)+(0.0391P)²+0.0520P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 
'Flack H D (1983), Acta Cryst. A39, 876-881, 927 Friedel Pairs'
_refine_ls_abs_structure_Flack   0.003(15)
_refine_ls_number_reflns         2324
_refine_ls_number_parameters     236
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0272
_refine_ls_R_factor_gt           0.0260
_refine_ls_wR_factor_ref         0.0659
_refine_ls_wR_factor_gt          0.0653
_refine_ls_goodness_of_fit_ref   1.071
_refine_ls_restrained_S_all      1.071
_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
C1 C 0.7863(3) -0.01581(19) 0.77310(7) 0.0207(4) Uani 1 1 d . . .
N1 N 0.5028(3) 0.12144(15) 0.86205(6) 0.0159(3) Uani 1 1 d . . .
O1 O 0.6699(2) 0.52611(13) 0.93484(5) 0.0197(3) Uani 1 1 d . . .
S1 S 0.31058(7) 0.08981(5) 0.911155(17) 0.01697(12) Uani 1 1 d . . .
C2 C 0.9486(3) -0.0369(2) 0.73235(8) 0.0216(4) Uani 1 1 d . . .
N2 N 0.4590(3) 0.16859(16) 0.95892(6) 0.0168(3) Uani 1 1 d . . .
H1N H 0.533(4) 0.115(2) 0.9769(8) 0.017(5) Uiso 1 1 d . . .
O2 O 0.3469(2) 0.45591(13) 0.97887(5) 0.0234(3) Uani 1 1 d . . .
C3 C 0.9309(3) 0.0383(2) 0.68408(8) 0.0245(4) Uani 1 1 d . . .
O3 O 0.1002(2) 0.16767(15) 0.90132(5) 0.0260(3) Uani 1 1 d . . .
C4 C 0.7517(4) 0.1347(2) 0.67715(8) 0.0284(5) Uani 1 1 d . . .
O4 O 0.2928(2) -0.05978(13) 0.92136(5) 0.0257(3) Uani 1 1 d . . .
C5 C 0.5858(4) 0.1535(2) 0.71756(8) 0.0235(4) Uani 1 1 d . . .
C6 C 0.6004(3) 0.07825(19) 0.76581(7) 0.0181(4) Uani 1 1 d . . .
C7 C 0.4095(3) 0.0924(2) 0.80785(7) 0.0208(4) Uani 1 1 d . . .
C8 C 0.5840(3) 0.26794(19) 0.87138(7) 0.0171(4) Uani 1 1 d . . .
C9 C 0.5997(3) 0.28271(19) 0.93426(7) 0.0166(4) Uani 1 1 d . . .
C10 C 0.5187(3) 0.42948(19) 0.95257(7) 0.0164(4) Uani 1 1 d . . .
C11 C 0.6260(4) 0.67413(19) 0.95090(8) 0.0204(4) Uani 1 1 d . . .
C12 C 0.7944(4) 0.7650(2) 0.91963(8) 0.0254(4) Uani 1 1 d . . .
H1 H 0.797(4) -0.066(2) 0.8076(9) 0.024(6) Uiso 1 1 d . . .
H2 H 1.068(4) -0.109(2) 0.7381(8) 0.021(5) Uiso 1 1 d . . .
H3 H 1.047(4) 0.026(2) 0.6570(9) 0.022(5) Uiso 1 1 d . . .
H4 H 0.740(4) 0.191(2) 0.6449(10) 0.033(6) Uiso 1 1 d . . .
H5 H 0.459(4) 0.219(2) 0.7122(8) 0.022(5) Uiso 1 1 d . . .
H6 H 0.749(4) 0.273(2) 0.9445(8) 0.012(5) Uiso 1 1 d . . .
H7 H 0.317(4) 0.004(3) 0.8080(9) 0.030(6) Uiso 1 1 d . . .
H8 H 0.294(4) 0.168(2) 0.7962(8) 0.020(5) Uiso 1 1 d . . .
H9 H 0.735(4) 0.281(2) 0.8558(9) 0.028(6) Uiso 1 1 d . . .
H10 H 0.481(3) 0.339(2) 0.8550(8) 0.013(5) Uiso 1 1 d . . .
H11 H 0.462(4) 0.700(2) 0.9421(8) 0.024(6) Uiso 1 1 d . . .
H12 H 0.659(4) 0.6846(19) 0.9897(8) 0.016(5) Uiso 1 1 d . . .
H13 H 0.787(4) 0.863(3) 0.9318(9) 0.041(7) Uiso 1 1 d . . .
H14 H 0.957(4) 0.733(2) 0.9269(8) 0.017(5) Uiso 1 1 d . . .
H15 H 0.761(4) 0.756(2) 0.8797(9) 0.029(6) Uiso 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
C1 C2 1.383(3) . ?
C1 C6 1.394(3) . ?
C1 H1 0.97(2) . ?
N1 C7 1.465(2) . ?
N1 C8 1.468(2) . ?
N1 S1 1.6628(14) . ?
O1 C10 1.327(2) . ?
O1 C11 1.465(2) . ?
S1 O4 1.4285(13) . ?
S1 O3 1.4285(14) . ?
S1 N2 1.6295(16) . ?
C2 C3 1.388(3) . ?
C2 H2 0.97(2) . ?
N2 C9 1.471(2) . ?
N2 H1N 0.80(2) . ?
O2 C10 1.204(2) . ?
C3 C4 1.378(3) . ?
C3 H3 0.95(2) . ?
C4 C5 1.388(3) . ?
C4 H4 0.95(2) . ?
C5 C6 1.386(3) . ?
C5 H5 0.96(2) . ?
C6 C7 1.512(2) . ?
C7 H7 0.98(2) . ?
C7 H8 1.01(2) . ?
C8 C9 1.560(3) . ?
C8 H9 0.95(2) . ?
C8 H10 0.98(2) . ?
C9 C10 1.521(2) . ?
C9 H6 0.90(2) . ?
C11 C12 1.500(3) . ?
C11 H11 0.99(2) . ?
C11 H12 0.98(2) . ?
C12 H13 0.97(3) . ?
C12 H14 0.99(2) . ?
C12 H15 1.01(2) . ?

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
C2 C1 C6 120.64(17) . . ?
C2 C1 H1 121.5(13) . . ?
C6 C1 H1 117.8(13) . . ?
C7 N1 C8 115.61(14) . . ?
C7 N1 S1 112.99(12) . . ?
C8 N1 S1 105.19(11) . . ?
C10 O1 C11 116.48(14) . . ?
O4 S1 O3 118.14(9) . . ?
O4 S1 N2 110.78(8) . . ?
O3 S1 N2 109.29(8) . . ?
O4 S1 N1 110.53(8) . . ?
O3 S1 N1 110.03(8) . . ?
N2 S1 N1 95.81(7) . . ?
C1 C2 C3 120.14(18) . . ?
C1 C2 H2 117.7(12) . . ?
C3 C2 H2 122.0(12) . . ?
C9 N2 S1 108.42(12) . . ?
C9 N2 H1N 113.6(15) . . ?
S1 N2 H1N 113.1(15) . . ?
C4 C3 C2 119.62(18) . . ?
C4 C3 H3 121.0(13) . . ?
C2 C3 H3 119.4(13) . . ?
C3 C4 C5 120.20(18) . . ?
C3 C4 H4 120.9(14) . . ?
C5 C4 H4 118.9(14) . . ?
C6 C5 C4 120.77(19) . . ?
C6 C5 H5 119.4(12) . . ?
C4 C5 H5 119.9(12) . . ?
C5 C6 C1 118.59(17) . . ?
C5 C6 C7 120.07(17) . . ?
C1 C6 C7 121.24(16) . . ?
N1 C7 C6 112.27(15) . . ?
N1 C7 H7 110.4(13) . . ?
C6 C7 H7 108.4(13) . . ?
N1 C7 H8 111.6(11) . . ?
C6 C7 H8 109.8(12) . . ?
H7 C7 H8 104.0(16) . . ?
N1 C8 C9 104.90(14) . . ?
N1 C8 H9 110.2(14) . . ?
C9 C8 H9 109.6(13) . . ?
N1 C8 H10 112.7(11) . . ?
C9 C8 H10 112.6(11) . . ?
H9 C8 H10 106.9(17) . . ?
N2 C9 C10 111.64(15) . . ?
N2 C9 C8 108.38(15) . . ?
C10 C9 C8 110.99(15) . . ?
N2 C9 H6 109.4(13) . . ?
C10 C9 H6 107.4(13) . . ?
C8 C9 H6 109.0(12) . . ?
O2 C10 O1 124.73(16) . . ?
O2 C10 C9 126.53(17) . . ?
O1 C10 C9 108.74(14) . . ?
O1 C11 C12 106.78(15) . . ?
O1 C11 H11 109.6(13) . . ?
C12 C11 H11 110.9(13) . . ?
O1 C11 H12 109.0(11) . . ?
C12 C11 H12 108.6(12) . . ?
H11 C11 H12 111.9(17) . . ?
C11 C12 H13 110.6(15) . . ?
C11 C12 H14 109.9(12) . . ?
H13 C12 H14 106(2) . . ?
C11 C12 H15 109.4(14) . . ?
H13 C12 H15 112.1(19) . . ?
H14 C12 H15 109.2(18) . . ?

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
C7 N1 S1 O4 77.64(15) . . . . ?
C8 N1 S1 O4 -155.37(11) . . . . ?
C7 N1 S1 O3 -54.61(15) . . . . ?
C8 N1 S1 O3 72.38(13) . . . . ?
C7 N1 S1 N2 -167.60(13) . . . . ?
C8 N1 S1 N2 -40.61(12) . . . . ?
C6 C1 C2 C3 1.6(3) . . . . ?
O4 S1 N2 C9 143.61(12) . . . . ?
O3 S1 N2 C9 -84.55(13) . . . . ?
N1 S1 N2 C9 29.05(13) . . . . ?
C1 C2 C3 C4 0.4(3) . . . . ?
C2 C3 C4 C5 -1.9(3) . . . . ?
C3 C4 C5 C6 1.4(3) . . . . ?
C4 C5 C6 C1 0.5(3) . . . . ?
C4 C5 C6 C7 -175.85(18) . . . . ?
C2 C1 C6 C5 -2.0(3) . . . . ?
C2 C1 C6 C7 174.32(17) . . . . ?
C8 N1 C7 C6 75.9(2) . . . . ?
S1 N1 C7 C6 -162.80(13) . . . . ?
C5 C6 C7 N1 -130.59(18) . . . . ?
C1 C6 C7 N1 53.1(2) . . . . ?
C7 N1 C8 C9 163.08(15) . . . . ?
S1 N1 C8 C9 37.70(16) . . . . ?
S1 N2 C9 C10 113.37(14) . . . . ?
S1 N2 C9 C8 -9.17(18) . . . . ?
N1 C8 C9 N2 -18.4(2) . . . . ?
N1 C8 C9 C10 -141.36(15) . . . . ?
C11 O1 C10 O2 2.7(2) . . . . ?
C11 O1 C10 C9 -177.21(14) . . . . ?
N2 C9 C10 O2 -8.0(2) . . . . ?
C8 C9 C10 O2 113.1(2) . . . . ?
N2 C9 C10 O1 171.92(14) . . . . ?
C8 C9 C10 O1 -67.05(19) . . . . ?
C10 O1 C11 C12 -171.50(15) . . . . ?

_diffrn_measured_fraction_theta_max 0.982
_diffrn_reflns_theta_full        67.34
_diffrn_measured_fraction_theta_full 0.982
_refine_diff_density_max         0.194
_refine_diff_density_min         -0.359
_refine_diff_density_rms         0.043
####################################################################### 
# 
# 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_v_77_1_0m
_database_code_depnum_ccdc_archive 'CCDC 1480994'
_audit_update_record             
;
2016-05-19 deposited with the CCDC.
2016-07-28 downloaded from the CCDC.
;
_audit_creation_date             2014-05-05
_audit_creation_method           
;
Olex2 1.2
(compiled 2014.03.20 svn.r2914 for OlexSys, GUI svn.r4816)
;
_shelxl_version_number           2013-4
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C13 H18 N2 O4 S'
_chemical_formula_sum            'C13 H18 N2 O4 S'
_chemical_formula_weight         298.35
_chemical_absolute_configuration ad
_chemical_melting_point          ?
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'

_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.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   6.1655(2)
_cell_length_b                   9.5773(3)
_cell_length_c                   24.0447(8)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1419.81(8)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3324
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      68.70
_cell_measurement_theta_min      3.68
_shelx_estimated_absorpt_T_max   0.938
_shelx_estimated_absorpt_T_min   0.670
_exptl_absorpt_coefficient_mu    2.173
_exptl_absorpt_correction_T_max  0.7532
_exptl_absorpt_correction_T_min  0.6076
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2012/1 (Bruker,2012) was used for absorption correction.
wR2(int) was 0.0843 before and 0.0691 after correction.
The Ratio of minimum to maximum transmission is 0.8067.
The λ/2 correction factor is 0.0015.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.396
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             632
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.03
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0478
_diffrn_reflns_av_unetI/netI     0.0420
_diffrn_reflns_Laue_measured_fraction_full 0.971
_diffrn_reflns_Laue_measured_fraction_max 0.961
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            9770
_diffrn_reflns_point_group_measured_fraction_full 0.971
_diffrn_reflns_point_group_measured_fraction_max 0.953
_diffrn_reflns_theta_full        66.595
_diffrn_reflns_theta_max         68.870
_diffrn_reflns_theta_min         3.676
_diffrn_ambient_temperature      100.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.971
_diffrn_measured_fraction_theta_max 0.961
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   'fine-focus sealed tube'
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.678
_reflns_Friedel_fraction_full    0.971
_reflns_Friedel_fraction_max     0.942
_reflns_number_gt                2366
_reflns_number_total             2515
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       ?
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    ?
_refine_diff_density_max         0.192
_refine_diff_density_min         -0.338
_refine_diff_density_rms         0.051
_refine_ls_abs_structure_details 
;
 Flack x determined using 940 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   0.032(12)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     186
_refine_ls_number_reflns         2515
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0332
_refine_ls_R_factor_gt           0.0304
_refine_ls_restrained_S_all      1.031
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0398P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0712
_refine_ls_wR_factor_ref         0.0723
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C2(H2)
2.b Secondary CH2 refined with riding coordinates:
 C3(H3A,H3B), C4(H4A,H4B), C6(H6A,H6B), C13(H13A,H13B)
2.c Aromatic/amide H refined with riding coordinates:
 C8(H8), C9(H9), C10(H10), C11(H11), C12(H12)
2.d Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
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 0.40658(10) 0.26547(6) 0.77090(2) 0.01355(16) Uani 1 1 d . . . . .
C1 C 0.4167(5) 0.4668(3) 0.62929(11) 0.0167(6) Uani 1 1 d . . . . .
C2 C 0.3149(4) 0.3840(3) 0.67643(11) 0.0156(6) Uani 1 1 d . . . . .
H2 H 0.2635 0.2926 0.6613 0.019 Uiso 1 1 calc R . . . .
C3 C 0.1204(5) 0.4602(3) 0.70225(11) 0.0173(6) Uani 1 1 d . . . . .
H3A H 0.1651 0.5553 0.7136 0.021 Uiso 1 1 calc R . . . .
H3B H 0.0042 0.4693 0.6741 0.021 Uiso 1 1 calc R . . . .
C4 C 0.0327(4) 0.3825(3) 0.75254(12) 0.0174(6) Uani 1 1 d . . . . .
H4A H -0.0864 0.4373 0.7694 0.021 Uiso 1 1 calc R . . . .
H4B H -0.0276 0.2916 0.7404 0.021 Uiso 1 1 calc R . . . .
C6 C 0.1190(5) 0.3233(3) 0.85030(11) 0.0169(6) Uani 1 1 d . . . . .
H6A H 0.2297 0.2707 0.8715 0.020 Uiso 1 1 calc R . . . .
H6B H -0.0115 0.2637 0.8467 0.020 Uiso 1 1 calc R . . . .
C7 C 0.0616(5) 0.4562(3) 0.88096(11) 0.0177(6) Uani 1 1 d . . . . .
C8 C 0.2123(5) 0.5633(3) 0.88620(14) 0.0268(7) Uani 1 1 d . . . . .
H8 H 0.3509 0.5542 0.8693 0.032 Uiso 1 1 calc R . . . .
C9 C 0.1624(6) 0.6825(3) 0.91569(15) 0.0327(8) Uani 1 1 d . . . . .
H9 H 0.2677 0.7544 0.9192 0.039 Uiso 1 1 calc R . . . .
C10 C -0.0388(5) 0.6988(3) 0.94027(13) 0.0268(7) Uani 1 1 d . . . . .
H10 H -0.0719 0.7808 0.9608 0.032 Uiso 1 1 calc R . . . .
C11 C -0.1918(5) 0.5935(3) 0.93445(12) 0.0257(7) Uani 1 1 d . . . . .
H11 H -0.3311 0.6038 0.9509 0.031 Uiso 1 1 calc R . . . .
C12 C -0.1428(5) 0.4736(3) 0.90490(12) 0.0213(6) Uani 1 1 d . . . . .
H12 H -0.2491 0.4025 0.9009 0.026 Uiso 1 1 calc R . . . .
C13 C 0.3363(5) 0.5902(3) 0.54694(12) 0.0268(7) Uani 1 1 d . . . . .
H13A H 0.4338 0.5348 0.5228 0.032 Uiso 1 1 calc R . . . .
H13B H 0.4166 0.6729 0.5605 0.032 Uiso 1 1 calc R . . . .
C14 C 0.1381(6) 0.6344(3) 0.51529(13) 0.0306(8) Uani 1 1 d . . . . .
H14A H 0.0610 0.5516 0.5019 0.046 Uiso 1 1 calc GR . . . .
H14B H 0.1813 0.6923 0.4836 0.046 Uiso 1 1 calc GR . . . .
H14C H 0.0426 0.6884 0.5398 0.046 Uiso 1 1 calc GR . . . .
N1 N 0.2036(4) 0.3581(2) 0.79476(9) 0.0160(5) Uani 1 1 d . . . . .
N2 N 0.4868(4) 0.3564(2) 0.71760(10) 0.0151(5) Uani 1 1 d . . . . .
O1 O 0.5742(3) 0.2658(2) 0.81203(7) 0.0181(4) Uani 1 1 d . . . . .
O2 O 0.3349(3) 0.1330(2) 0.74948(8) 0.0202(5) Uani 1 1 d . . . . .
O3 O 0.6056(3) 0.4928(2) 0.62417(8) 0.0227(5) Uani 1 1 d . . . . .
O4 O 0.2617(3) 0.5063(2) 0.59336(8) 0.0221(5) Uani 1 1 d . . . . .
H2A H 0.546(5) 0.429(4) 0.7271(14) 0.021(9) Uiso 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 N1 1.638(2) . ?
S1 N2 1.626(2) . ?
S1 O1 1.4303(19) . ?
S1 O2 1.439(2) . ?
C1 C2 1.519(4) . ?
C1 O3 1.198(4) . ?
C1 O4 1.343(4) . ?
C2 H2 1.0000 . ?
C2 C3 1.535(4) . ?
C2 N2 1.474(3) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C3 C4 1.519(4) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C4 N1 1.482(3) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C6 C7 1.513(4) . ?
C6 N1 1.472(4) . ?
C7 C8 1.389(4) . ?
C7 C12 1.395(4) . ?
C8 H8 0.9500 . ?
C8 C9 1.379(5) . ?
C9 H9 0.9500 . ?
C9 C10 1.383(5) . ?
C10 H10 0.9500 . ?
C10 C11 1.388(5) . ?
C11 H11 0.9500 . ?
C11 C12 1.384(4) . ?
C12 H12 0.9500 . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C13 C14 1.501(4) . ?
C13 O4 1.450(4) . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
N2 H2A 0.82(4) . ?

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
N2 S1 N1 102.61(12) . . ?
O1 S1 N1 107.97(12) . . ?
O1 S1 N2 108.91(12) . . ?
O1 S1 O2 118.11(12) . . ?
O2 S1 N1 111.61(12) . . ?
O2 S1 N2 106.47(12) . . ?
O3 C1 C2 126.0(3) . . ?
O3 C1 O4 124.6(3) . . ?
O4 C1 C2 109.5(2) . . ?
C1 C2 H2 108.4 . . ?
C1 C2 C3 112.1(2) . . ?
C3 C2 H2 108.4 . . ?
N2 C2 C1 107.3(2) . . ?
N2 C2 H2 108.4 . . ?
N2 C2 C3 112.0(2) . . ?
C2 C3 H3A 109.3 . . ?
C2 C3 H3B 109.3 . . ?
H3A C3 H3B 108.0 . . ?
C4 C3 C2 111.5(2) . . ?
C4 C3 H3A 109.3 . . ?
C4 C3 H3B 109.3 . . ?
C3 C4 H4A 109.3 . . ?
C3 C4 H4B 109.3 . . ?
H4A C4 H4B 107.9 . . ?
N1 C4 C3 111.7(2) . . ?
N1 C4 H4A 109.3 . . ?
N1 C4 H4B 109.3 . . ?
H6A C6 H6B 108.2 . . ?
C7 C6 H6A 109.8 . . ?
C7 C6 H6B 109.8 . . ?
N1 C6 H6A 109.8 . . ?
N1 C6 H6B 109.8 . . ?
N1 C6 C7 109.5(2) . . ?
C8 C7 C6 120.6(3) . . ?
C8 C7 C12 118.6(3) . . ?
C12 C7 C6 120.8(3) . . ?
C7 C8 H8 119.7 . . ?
C9 C8 C7 120.6(3) . . ?
C9 C8 H8 119.7 . . ?
C8 C9 H9 119.6 . . ?
C8 C9 C10 120.8(3) . . ?
C10 C9 H9 119.6 . . ?
C9 C10 H10 120.5 . . ?
C9 C10 C11 119.0(3) . . ?
C11 C10 H10 120.5 . . ?
C10 C11 H11 119.8 . . ?
C12 C11 C10 120.4(3) . . ?
C12 C11 H11 119.8 . . ?
C7 C12 H12 119.7 . . ?
C11 C12 C7 120.5(3) . . ?
C11 C12 H12 119.7 . . ?
H13A C13 H13B 108.6 . . ?
C14 C13 H13A 110.4 . . ?
C14 C13 H13B 110.4 . . ?
O4 C13 H13A 110.4 . . ?
O4 C13 H13B 110.4 . . ?
O4 C13 C14 106.8(3) . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C4 N1 S1 112.87(18) . . ?
C6 N1 S1 117.76(19) . . ?
C6 N1 C4 113.9(2) . . ?
S1 N2 H2A 112(2) . . ?
C2 N2 S1 113.99(18) . . ?
C2 N2 H2A 111(2) . . ?
C1 O4 C13 115.2(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
C1 C2 C3 C4 -175.0(2) . . . . ?
C1 C2 N2 S1 -178.95(18) . . . . ?
C2 C1 O4 C13 178.2(2) . . . . ?
C2 C3 C4 N1 55.5(3) . . . . ?
C3 C2 N2 S1 57.5(3) . . . . ?
C3 C4 N1 S1 -59.9(3) . . . . ?
C3 C4 N1 C6 162.3(2) . . . . ?
C6 C7 C8 C9 -177.9(3) . . . . ?
C6 C7 C12 C11 177.9(3) . . . . ?
C7 C6 N1 S1 141.1(2) . . . . ?
C7 C6 N1 C4 -83.3(3) . . . . ?
C7 C8 C9 C10 -0.6(5) . . . . ?
C8 C7 C12 C11 -1.7(4) . . . . ?
C8 C9 C10 C11 -0.6(5) . . . . ?
C9 C10 C11 C12 0.6(5) . . . . ?
C10 C11 C12 C7 0.6(5) . . . . ?
C12 C7 C8 C9 1.7(5) . . . . ?
C14 C13 O4 C1 -174.6(2) . . . . ?
N1 S1 N2 C2 -55.9(2) . . . . ?
N1 C6 C7 C8 -52.7(4) . . . . ?
N1 C6 C7 C12 127.8(3) . . . . ?
N2 S1 N1 C4 56.8(2) . . . . ?
N2 S1 N1 C6 -167.3(2) . . . . ?
N2 C2 C3 C4 -54.2(3) . . . . ?
O1 S1 N1 C4 171.71(18) . . . . ?
O1 S1 N1 C6 -52.3(2) . . . . ?
O1 S1 N2 C2 -170.16(18) . . . . ?
O2 S1 N1 C4 -56.9(2) . . . . ?
O2 S1 N1 C6 79.1(2) . . . . ?
O2 S1 N2 C2 61.5(2) . . . . ?
O3 C1 C2 C3 129.9(3) . . . . ?
O3 C1 C2 N2 6.5(4) . . . . ?
O3 C1 O4 C13 -2.2(4) . . . . ?
O4 C1 C2 C3 -50.5(3) . . . . ?
O4 C1 C2 N2 -174.0(2) . . . . ?

####################################################################### 
# 
# 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_lk_4_36_0m
_database_code_depnum_ccdc_archive 'CCDC 1480995'
_audit_update_record             
;
2016-05-19 deposited with the CCDC.
2016-07-28 downloaded from the CCDC.
;
_audit_creation_date             2014-08-01
_audit_creation_method           
;
Olex2 1.2
(compiled 2014.07.22 svn.r2960 for OlexSys, GUI svn.r4862)
;
_shelxl_version_number           2014-3
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C15 H17 N3 O4 S'
_chemical_formula_sum            'C15 H17 N3 O4 S'
_chemical_formula_weight         335.38
_chemical_absolute_configuration ad
_chemical_melting_point          ?
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'

_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.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
'-x+1/2, -y, z+1/2'

_cell_length_a                   6.0617(2)
_cell_length_b                   7.1812(2)
_cell_length_c                   35.5229(10)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1546.32(8)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9915
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      69.02
_cell_measurement_theta_min      4.98
_shelx_estimated_absorpt_T_max   0.959
_shelx_estimated_absorpt_T_min   0.624
_exptl_absorpt_coefficient_mu    2.086
_exptl_absorpt_correction_T_max  0.7532
_exptl_absorpt_correction_T_min  0.4798
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2014/2 (Bruker,2014) was used for absorption correction.
wR2(int) was 0.1620 before and 0.0935 after correction.
The Ratio of minimum to maximum transmission is 0.6370.
The λ/2 correction factor is 0.00150.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.441
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             704
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.02
_exptl_crystal_size_min          0.02
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0655
_diffrn_reflns_av_unetI/netI     0.0368
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       42
_diffrn_reflns_limit_l_min       -42
_diffrn_reflns_number            19967
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         69.325
_diffrn_reflns_theta_min         4.980
_diffrn_ambient_temperature      100.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Bruker D8 Venture PHOTON 100 CMOS'
_diffrn_measurement_method       'omega scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   'INCOATEC Imus micro-focus source'
_diffrn_radiation_monochromator  mirrors
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.662
_reflns_Friedel_fraction_full    0.992
_reflns_Friedel_fraction_max     0.976
_reflns_number_gt                2715
_reflns_number_total             2863
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    ?
_refine_diff_density_max         0.299
_refine_diff_density_min         -0.306
_refine_diff_density_rms         0.058
_refine_ls_abs_structure_details 
;
 Flack x determined using 1072 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.086(9)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     216
_refine_ls_number_reflns         2863
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0349
_refine_ls_R_factor_gt           0.0323
_refine_ls_restrained_S_all      1.026
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0524P)²+0.4201P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0833
_refine_ls_wR_factor_ref         0.0849
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C5(H5A,H5B), C6(H6A,H6B), C7(H7A,H7B)
2.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C9(H9), C10(H10), C11(H11), C12(H12), C13(H13), C14(H14),
 C15(H15)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
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 0.90474(9) 0.48853(8) 0.97162(2) 0.01325(17) Uani 1 1 d . . . . .
O1 O 0.9975(4) 0.6731(5) 0.74262(6) 0.0461(7) Uani 1 1 d . . . . .
O2 O 1.3192(3) 0.6328(4) 0.76704(6) 0.0362(6) Uani 1 1 d . . . . .
O3 O 1.0549(3) 0.6414(3) 0.97005(5) 0.0184(4) Uani 1 1 d . . . . .
O4 O 0.9908(3) 0.3028(3) 0.96957(6) 0.0201(4) Uani 1 1 d . . . . .
C16 C 0.8668(4) 0.8061(3) 0.87666(7) 0.0167(5) Uani 1 1 d . . . . .
N2 N 0.7358(3) 0.5129(3) 0.93584(5) 0.0138(4) Uani 1 1 d . . . . .
N3 N 0.7770(4) 0.5036(4) 1.01156(6) 0.0163(4) Uani 1 1 d . . . . .
N4 N 1.1237(4) 0.6711(4) 0.76940(7) 0.0276(6) Uani 1 1 d . . . . .
C2 C 1.0323(4) 0.7171(4) 0.80683(8) 0.0199(6) Uani 1 1 d . . . . .
C3 C 1.1604(4) 0.6803(4) 0.83818(8) 0.0199(6) Uani 1 1 d . . . . .
H3 H 1.3028 0.6263 0.8358 0.024 Uiso 1 1 calc R . . . .
C4 C 1.0736(5) 0.7252(4) 0.87324(8) 0.0193(5) Uani 1 1 d . . . . .
H4 H 1.1574 0.7001 0.8953 0.023 Uiso 1 1 calc R . . . .
C5 C 0.7737(5) 0.8532(4) 0.91498(7) 0.0196(6) Uani 1 1 d . . . . .
H5A H 0.6841 0.9680 0.9129 0.024 Uiso 1 1 calc R . . . .
H5B H 0.8972 0.8794 0.9324 0.024 Uiso 1 1 calc R . . . .
C6 C 0.6304(4) 0.6984(4) 0.93177(7) 0.0176(5) Uani 1 1 d . . . . .
H6A H 0.5797 0.7393 0.9569 0.021 Uiso 1 1 calc R . . . .
H6B H 0.4978 0.6841 0.9158 0.021 Uiso 1 1 calc R . . . .
C7 C 0.5727(4) 0.3592(4) 0.93247(7) 0.0170(5) Uani 1 1 d . . . . .
H7A H 0.4372 0.3931 0.9464 0.020 Uiso 1 1 calc R . . . .
H7B H 0.6343 0.2452 0.9441 0.020 Uiso 1 1 calc R . . . .
C8 C 0.5138(4) 0.3191(3) 0.89165(7) 0.0151(5) Uani 1 1 d . . . . .
C9 C 0.6659(4) 0.3473(4) 0.86298(7) 0.0177(5) Uani 1 1 d . . . . .
H9 H 0.8072 0.3973 0.8686 0.021 Uiso 1 1 calc R . . . .
C10 C 0.6110(5) 0.3019(4) 0.82579(7) 0.0201(6) Uani 1 1 d . . . . .
H10 H 0.7151 0.3221 0.8062 0.024 Uiso 1 1 calc R . . . .
C11 C 0.4062(5) 0.2278(4) 0.81740(7) 0.0203(6) Uani 1 1 d . . . . .
H11 H 0.3700 0.1965 0.7922 0.024 Uiso 1 1 calc R . . . .
C12 C 0.8254(5) 0.7964(4) 0.80897(8) 0.0224(6) Uani 1 1 d . . . . .
H12 H 0.7414 0.8195 0.7869 0.027 Uiso 1 1 calc R . . . .
C13 C 0.7433(4) 0.8415(4) 0.84443(8) 0.0199(6) Uani 1 1 d . . . . .
H13 H 0.6016 0.8970 0.8466 0.024 Uiso 1 1 calc R . . . .
C14 C 0.2537(4) 0.1993(4) 0.84595(8) 0.0191(6) Uani 1 1 d . . . . .
H14 H 0.1130 0.1482 0.8403 0.023 Uiso 1 1 calc R . . . .
C15 C 0.3071(4) 0.2460(4) 0.88310(7) 0.0173(5) Uani 1 1 d . . . . .
H15 H 0.2019 0.2276 0.9026 0.021 Uiso 1 1 calc R . . . .
H3A H 0.713(5) 0.603(5) 1.0151(8) 0.010(7) Uiso 1 1 d . . . . .
H3B H 0.670(5) 0.416(5) 1.0159(9) 0.018(8) Uiso 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 O3 1.427(2) . ?
S1 O4 1.4338(18) . ?
S1 N2 1.642(2) . ?
S1 N3 1.620(2) . ?
O1 N4 1.221(3) . ?
O2 N4 1.219(3) . ?
C16 C4 1.387(4) . ?
C16 C5 1.512(4) . ?
C16 C13 1.392(4) . ?
N2 C6 1.485(3) . ?
N2 C7 1.487(3) . ?
N3 H3A 0.82(3) . ?
N3 H3B 0.92(4) . ?
N4 C2 1.478(4) . ?
C2 C3 1.383(4) . ?
C2 C12 1.379(4) . ?
C3 H3 0.9500 . ?
C3 C4 1.390(4) . ?
C4 H4 0.9500 . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C5 C6 1.532(4) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C7 C8 1.521(3) . ?
C8 C9 1.388(4) . ?
C8 C15 1.392(4) . ?
C9 H9 0.9500 . ?
C9 C10 1.401(4) . ?
C10 H10 0.9500 . ?
C10 C11 1.384(4) . ?
C11 H11 0.9500 . ?
C11 C14 1.387(4) . ?
C12 H12 0.9500 . ?
C12 C13 1.393(4) . ?
C13 H13 0.9500 . ?
C14 H14 0.9500 . ?
C14 C15 1.400(4) . ?
C15 H15 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
O3 S1 O4 118.75(11) . . ?
O3 S1 N2 106.60(11) . . ?
O3 S1 N3 106.73(12) . . ?
O4 S1 N2 106.66(12) . . ?
O4 S1 N3 106.31(13) . . ?
N3 S1 N2 111.90(11) . . ?
C4 C16 C5 120.7(2) . . ?
C4 C16 C13 119.4(3) . . ?
C13 C16 C5 119.9(2) . . ?
C6 N2 S1 116.06(17) . . ?
C6 N2 C7 111.83(19) . . ?
C7 N2 S1 113.46(16) . . ?
S1 N3 H3A 115(2) . . ?
S1 N3 H3B 116(2) . . ?
H3A N3 H3B 104(3) . . ?
O1 N4 C2 117.6(2) . . ?
O2 N4 O1 123.9(3) . . ?
O2 N4 C2 118.5(2) . . ?
C3 C2 N4 118.1(2) . . ?
C12 C2 N4 118.9(2) . . ?
C12 C2 C3 123.0(3) . . ?
C2 C3 H3 121.2 . . ?
C2 C3 C4 117.7(3) . . ?
C4 C3 H3 121.2 . . ?
C16 C4 C3 121.2(2) . . ?
C16 C4 H4 119.4 . . ?
C3 C4 H4 119.4 . . ?
C16 C5 H5A 108.9 . . ?
C16 C5 H5B 108.9 . . ?
C16 C5 C6 113.6(2) . . ?
H5A C5 H5B 107.7 . . ?
C6 C5 H5A 108.9 . . ?
C6 C5 H5B 108.9 . . ?
N2 C6 C5 116.4(2) . . ?
N2 C6 H6A 108.2 . . ?
N2 C6 H6B 108.2 . . ?
C5 C6 H6A 108.2 . . ?
C5 C6 H6B 108.2 . . ?
H6A C6 H6B 107.3 . . ?
N2 C7 H7A 109.2 . . ?
N2 C7 H7B 109.2 . . ?
N2 C7 C8 111.9(2) . . ?
H7A C7 H7B 107.9 . . ?
C8 C7 H7A 109.2 . . ?
C8 C7 H7B 109.2 . . ?
C9 C8 C7 121.1(2) . . ?
C9 C8 C15 119.5(2) . . ?
C15 C8 C7 119.4(2) . . ?
C8 C9 H9 120.0 . . ?
C8 C9 C10 120.0(2) . . ?
C10 C9 H9 120.0 . . ?
C9 C10 H10 119.8 . . ?
C11 C10 C9 120.4(3) . . ?
C11 C10 H10 119.8 . . ?
C10 C11 H11 120.1 . . ?
C10 C11 C14 119.8(2) . . ?
C14 C11 H11 120.1 . . ?
C2 C12 H12 121.0 . . ?
C2 C12 C13 118.1(3) . . ?
C13 C12 H12 121.0 . . ?
C16 C13 C12 120.6(3) . . ?
C16 C13 H13 119.7 . . ?
C12 C13 H13 119.7 . . ?
C11 C14 H14 120.0 . . ?
C11 C14 C15 120.0(2) . . ?
C15 C14 H14 120.0 . . ?
C8 C15 C14 120.3(2) . . ?
C8 C15 H15 119.9 . . ?
C14 C15 H15 119.9 . . ?

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
S1 N2 C6 C5 77.8(3) . . . . ?
S1 N2 C7 C8 -147.28(18) . . . . ?
O1 N4 C2 C3 167.6(3) . . . . ?
O1 N4 C2 C12 -13.2(4) . . . . ?
O2 N4 C2 C3 -12.2(4) . . . . ?
O2 N4 C2 C12 167.0(3) . . . . ?
O3 S1 N2 C6 -50.75(19) . . . . ?
O3 S1 N2 C7 177.69(17) . . . . ?
O4 S1 N2 C6 -178.56(17) . . . . ?
O4 S1 N2 C7 49.88(19) . . . . ?
C16 C5 C6 N2 56.6(3) . . . . ?
N2 C7 C8 C9 30.7(3) . . . . ?
N2 C7 C8 C15 -151.9(2) . . . . ?
N3 S1 N2 C6 65.6(2) . . . . ?
N3 S1 N2 C7 -66.0(2) . . . . ?
N4 C2 C3 C4 179.6(2) . . . . ?
N4 C2 C12 C13 -179.0(2) . . . . ?
C2 C3 C4 C16 -0.7(4) . . . . ?
C2 C12 C13 C16 -0.4(4) . . . . ?
C3 C2 C12 C13 0.2(4) . . . . ?
C4 C16 C5 C6 -92.8(3) . . . . ?
C4 C16 C13 C12 0.1(4) . . . . ?
C5 C16 C4 C3 179.6(3) . . . . ?
C5 C16 C13 C12 -179.1(2) . . . . ?
C6 N2 C7 C8 79.1(3) . . . . ?
C7 N2 C6 C5 -149.9(2) . . . . ?
C7 C8 C9 C10 177.3(2) . . . . ?
C7 C8 C15 C14 -176.8(2) . . . . ?
C8 C9 C10 C11 -0.4(4) . . . . ?
C9 C8 C15 C14 0.6(4) . . . . ?
C9 C10 C11 C14 0.4(4) . . . . ?
C10 C11 C14 C15 0.1(4) . . . . ?
C11 C14 C15 C8 -0.7(4) . . . . ?
C12 C2 C3 C4 0.4(4) . . . . ?
C13 C16 C4 C3 0.5(4) . . . . ?
C13 C16 C5 C6 86.3(3) . . . . ?
C15 C8 C9 C10 -0.1(4) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_lk_3_287a_0m_a
_database_code_depnum_ccdc_archive 'CCDC 1480996'
_audit_update_record             
;
2016-05-19 deposited with the CCDC.
2016-07-28 downloaded from the CCDC.
;
_audit_creation_date             2014-08-04
_audit_creation_method           
;
Olex2 1.2
(compiled 2014.07.22 svn.r2960 for OlexSys, GUI svn.r4862)
;
_shelxl_version_number           2014-3
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C22 H22 N2 O2 S'
_chemical_formula_sum            'C22 H22 N2 O2 S'
_chemical_formula_weight         378.47
_chemical_melting_point          ?
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'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   10.1061(3)
_cell_length_b                   18.1581(5)
_cell_length_c                   20.5423(6)
_cell_angle_alpha                90
_cell_angle_beta                 90.2280(10)
_cell_angle_gamma                90
_cell_volume                     3769.64(19)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    9737
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      68.98
_cell_measurement_theta_min      3.25
_shelx_estimated_absorpt_T_max   0.967
_shelx_estimated_absorpt_T_min   0.824
_exptl_absorpt_coefficient_mu    1.680
_exptl_absorpt_correction_T_max  0.7533
_exptl_absorpt_correction_T_min  0.6673
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2014/2 (Bruker,2014) was used for absorption correction.
wR2(int) was 0.0713 before and 0.0576 after correction.
The Ratio of minimum to maximum transmission is 0.8858.
The λ/2 correction factor is 0.00150.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.334
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1600
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.03
_exptl_crystal_size_min          0.02
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0432
_diffrn_reflns_av_unetI/netI     0.0223
_diffrn_reflns_Laue_measured_fraction_full 0.988
_diffrn_reflns_Laue_measured_fraction_max 0.980
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            49569
_diffrn_reflns_point_group_measured_fraction_full 0.988
_diffrn_reflns_point_group_measured_fraction_max 0.980
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         69.410
_diffrn_reflns_theta_min         3.248
_diffrn_ambient_temperature      100.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.980
_diffrn_measurement_device_type  'Bruker D8 Venture PHOTON 100 CMOS'
_diffrn_measurement_method       'omega scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   'INCOATEC Imus micro-focus source'
_diffrn_radiation_monochromator  mirrors
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                5982
_reflns_number_total             6932
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    ?
_refine_diff_density_max         0.396
_refine_diff_density_min         -0.278
_refine_diff_density_rms         0.083
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     495
_refine_ls_number_reflns         6932
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0424
_refine_ls_R_factor_gt           0.0345
_refine_ls_restrained_S_all      1.058
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0457P)²+1.2559P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0821
_refine_ls_wR_factor_ref         0.0880
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Ternary CH refined with riding coordinates:
 C7(H7), C15(H15), C19(H19), C23(H23)
2.b Secondary CH2 refined with riding coordinates:
 C5(H5A,H5B), C21(H21A,H21B), C30(H30A,H30B), C37(H37A,H37B)
2.c Aromatic/amide H refined with riding coordinates:
 C3(H3A), C6(H6), C8(H8), C9(H9), C10(H10), C12(H12), C14(H14), C16(H16),
 C17(H17), C18(H18), C20(H20), C22(H22), C24(H24), C25(H25), C27(H27), C28(H28),
  C29(H29), C31(H31), C32(H32), C33(H33), C34(H34), C35(H35), C36(H36),
 C38(H38), C39(H39), C40(H40), C41(H41), C42(H42), C43(H43), C44(H44)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
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 0.29721(3) 0.50817(2) 0.73602(2) 0.02128(10) Uani 1 1 d . . . . .
S2 S 0.43081(3) 0.73542(2) 0.65675(2) 0.01973(9) Uani 1 1 d . . . . .
O1 O 0.30453(10) 0.69973(7) 0.66573(5) 0.0282(2) Uani 1 1 d . . . . .
O2 O 0.42379(10) 0.54241(6) 0.72368(6) 0.0277(2) Uani 1 1 d . . . . .
O3 O 0.28643(11) 0.43312(6) 0.71565(6) 0.0298(3) Uani 1 1 d . . . . .
O4 O 0.43352(12) 0.81143(6) 0.67485(5) 0.0304(3) Uani 1 1 d . . . . .
N1 N 0.49055(12) 0.72696(7) 0.58353(6) 0.0185(2) Uani 1 1 d . . . . .
N2 N 0.25035(12) 0.51462(7) 0.81222(6) 0.0212(3) Uani 1 1 d . . . . .
N3 N 0.17910(12) 0.56037(7) 0.70589(6) 0.0218(3) Uani 1 1 d . . . . .
N4 N 0.54550(12) 0.68625(7) 0.69329(6) 0.0200(3) Uani 1 1 d . . . . .
C1 C 0.63505(14) 0.54031(8) 0.53666(7) 0.0190(3) Uani 1 1 d . . . . .
C2 C 0.77411(14) 0.70854(8) 0.65156(7) 0.0181(3) Uani 1 1 d . . . . .
C3 C 0.69287(15) 0.54921(8) 0.47546(7) 0.0222(3) Uani 1 1 d . . . . .
H3A H 0.6594 0.5856 0.4465 0.027 Uiso 1 1 calc R . . . .
C4 C 0.47842(14) 0.75416(8) 0.46689(7) 0.0195(3) Uani 1 1 d . . . . .
C5 C 0.52526(14) 0.59133(8) 0.55736(7) 0.0190(3) Uani 1 1 d . . . . .
H5A H 0.4763 0.5695 0.5943 0.023 Uiso 1 1 calc R . . . .
H5B H 0.4624 0.5987 0.5208 0.023 Uiso 1 1 calc R . . . .
C6 C -0.05705(15) 0.47373(8) 0.73604(8) 0.0233(3) Uani 1 1 d . . . . .
H6 H 0.0167 0.4488 0.7179 0.028 Uiso 1 1 calc R . . . .
C7 C 0.58511(13) 0.66575(7) 0.57787(7) 0.0164(3) Uani 1 1 d . . . . .
H7 H 0.6547 0.6798 0.5457 0.020 Uiso 1 1 calc R . . . .
C8 C 0.77874(15) 0.77816(8) 0.67937(7) 0.0218(3) Uani 1 1 d . . . . .
H8 H 0.7011 0.7990 0.6976 0.026 Uiso 1 1 calc R . . . .
C9 C -0.15329(14) 0.58203(8) 0.78247(7) 0.0199(3) Uani 1 1 d . . . . .
H9 H -0.1452 0.6315 0.7971 0.024 Uiso 1 1 calc R . . . .
C10 C 1.00726(15) 0.71702(9) 0.62763(7) 0.0257(3) Uani 1 1 d . . . . .
H10 H 1.0854 0.6959 0.6101 0.031 Uiso 1 1 calc R . . . .
C11 C -0.04290(14) 0.54549(8) 0.75805(7) 0.0178(3) Uani 1 1 d . . . . .
C12 C 0.88955(14) 0.67794(8) 0.62581(7) 0.0219(3) Uani 1 1 d . . . . .
H12 H 0.8873 0.6302 0.6070 0.026 Uiso 1 1 calc R . . . .
C13 C 0.14095(15) 0.70531(8) 0.86835(7) 0.0216(3) Uani 1 1 d . . . . .
C14 C -0.28781(14) 0.47449(9) 0.76527(7) 0.0228(3) Uani 1 1 d . . . . .
H14 H -0.3706 0.4500 0.7683 0.027 Uiso 1 1 calc R . . . .
C15 C 0.08781(14) 0.58612(8) 0.75764(7) 0.0182(3) Uani 1 1 d . . . . .
H15 H 0.0689 0.6394 0.7497 0.022 Uiso 1 1 calc R . . . .
C16 C 0.44622(15) 0.71316(8) 0.41186(8) 0.0237(3) Uani 1 1 d . . . . .
H16 H 0.3740 0.6797 0.4132 0.028 Uiso 1 1 calc R . . . .
C17 C -0.27519(14) 0.54677(8) 0.78557(7) 0.0219(3) Uani 1 1 d . . . . .
H17 H -0.3501 0.5724 0.8017 0.026 Uiso 1 1 calc R . . . .
C18 C 0.58517(15) 0.80290(8) 0.46416(7) 0.0223(3) Uani 1 1 d . . . . .
H18 H 0.6083 0.8313 0.5014 0.027 Uiso 1 1 calc R . . . .
C19 C 0.64923(13) 0.66297(8) 0.64676(7) 0.0171(3) Uani 1 1 d . . . . .
H19 H 0.6727 0.6106 0.6565 0.021 Uiso 1 1 calc R . . . .
C20 C 0.68538(15) 0.48677(8) 0.57831(8) 0.0226(3) Uani 1 1 d . . . . .
H20 H 0.6470 0.4800 0.6200 0.027 Uiso 1 1 calc R . . . .
C21 C 0.40087(14) 0.74472(8) 0.52887(7) 0.0213(3) Uani 1 1 d . . . . .
H21A H 0.3521 0.7907 0.5386 0.026 Uiso 1 1 calc R . . . .
H21B H 0.3354 0.7046 0.5233 0.026 Uiso 1 1 calc R . . . .
C22 C 0.10765(16) 0.69879(9) 0.93390(8) 0.0265(3) Uani 1 1 d . . . . .
H22 H 0.1530 0.6642 0.9606 0.032 Uiso 1 1 calc R . . . .
C23 C 0.16635(14) 0.57990(8) 0.82278(7) 0.0188(3) Uani 1 1 d . . . . .
H23 H 0.1026 0.5688 0.8586 0.023 Uiso 1 1 calc R . . . .
C24 C 1.01139(16) 0.78683(9) 0.65493(8) 0.0284(3) Uani 1 1 d . . . . .
H24 H 1.0921 0.8137 0.6561 0.034 Uiso 1 1 calc R . . . .
C25 C 0.07316(16) 0.75652(8) 0.83046(8) 0.0259(3) Uani 1 1 d . . . . .
H25 H 0.0952 0.7621 0.7858 0.031 Uiso 1 1 calc R . . . .
C26 C 0.29795(15) 0.49449(8) 0.92921(8) 0.0239(3) Uani 1 1 d . . . . .
C27 C 0.51894(17) 0.72064(9) 0.35469(8) 0.0280(3) Uani 1 1 d . . . . .
H27 H 0.4959 0.6927 0.3172 0.034 Uiso 1 1 calc R . . . .
C28 C 0.79886(16) 0.50539(9) 0.45645(8) 0.0280(3) Uani 1 1 d . . . . .
H28 H 0.8374 0.5119 0.4147 0.034 Uiso 1 1 calc R . . . .
C29 C 0.18967(16) 0.45109(9) 0.94615(8) 0.0279(3) Uani 1 1 d . . . . .
H29 H 0.1504 0.4194 0.9148 0.034 Uiso 1 1 calc R . . . .
C30 C 0.23937(14) 0.65229(8) 0.83922(7) 0.0219(3) Uani 1 1 d . . . . .
H30A H 0.3119 0.6426 0.8706 0.026 Uiso 1 1 calc R . . . .
H30B H 0.2782 0.6736 0.7993 0.026 Uiso 1 1 calc R . . . .
C31 C 0.89658(16) 0.81730(9) 0.68059(8) 0.0272(3) Uani 1 1 d . . . . .
H31 H 0.8989 0.8652 0.6991 0.033 Uiso 1 1 calc R . . . .
C32 C 0.79201(16) 0.44288(9) 0.55929(8) 0.0281(3) Uani 1 1 d . . . . .
H32 H 0.8260 0.4065 0.5881 0.034 Uiso 1 1 calc R . . . .
C33 C -0.17831(16) 0.43807(9) 0.74035(8) 0.0268(3) Uani 1 1 d . . . . .
H33 H -0.1864 0.3885 0.7262 0.032 Uiso 1 1 calc R . . . .
C34 C 0.65739(16) 0.80999(9) 0.40744(8) 0.0266(3) Uani 1 1 d . . . . .
H34 H 0.7300 0.8432 0.4058 0.032 Uiso 1 1 calc R . . . .
C35 C 0.84826(16) 0.45217(9) 0.49857(9) 0.0301(4) Uani 1 1 d . . . . .
H35 H 0.9206 0.4222 0.4857 0.036 Uiso 1 1 calc R . . . .
C36 C -0.02657(17) 0.79973(9) 0.85722(9) 0.0320(4) Uani 1 1 d . . . . .
H36 H -0.0730 0.8340 0.8307 0.038 Uiso 1 1 calc R . . . .
C37 C 0.35232(15) 0.49329(9) 0.86081(8) 0.0267(3) Uani 1 1 d . . . . .
H37A H 0.4281 0.5277 0.8579 0.032 Uiso 1 1 calc R . . . .
H37B H 0.3850 0.4432 0.8507 0.032 Uiso 1 1 calc R . . . .
C38 C 0.35519(17) 0.53934(9) 0.97637(8) 0.0304(4) Uani 1 1 d . . . . .
H38 H 0.4299 0.5686 0.9656 0.036 Uiso 1 1 calc R . . . .
C39 C 0.62419(17) 0.76869(9) 0.35270(8) 0.0282(3) Uani 1 1 d . . . . .
H39 H 0.6742 0.7737 0.3139 0.034 Uiso 1 1 calc R . . . .
C40 C 0.00881(18) 0.74230(10) 0.96052(9) 0.0333(4) Uani 1 1 d . . . . .
H40 H -0.0130 0.7373 1.0053 0.040 Uiso 1 1 calc R . . . .
C41 C -0.05810(17) 0.79282(9) 0.92241(9) 0.0343(4) Uani 1 1 d . . . . .
H41 H -0.1254 0.8227 0.9409 0.041 Uiso 1 1 calc R . . . .
C42 C 0.3041(2) 0.54181(10) 1.03917(8) 0.0365(4) Uani 1 1 d . . . . .
H42 H 0.3444 0.5723 1.0712 0.044 Uiso 1 1 calc R . . . .
C43 C 0.13912(18) 0.45418(10) 1.00880(9) 0.0351(4) Uani 1 1 d . . . . .
H43 H 0.0653 0.4245 1.0200 0.042 Uiso 1 1 calc R . . . .
C44 C 0.19492(19) 0.49990(10) 1.05493(8) 0.0357(4) Uani 1 1 d . . . . .
H44 H 0.1583 0.5025 1.0974 0.043 Uiso 1 1 calc R . . . .
H3 H 0.2147(19) 0.5964(11) 0.6863(9) 0.025(5) Uiso 1 1 d . . . . .
H4 H 0.511(2) 0.6495(11) 0.7105(10) 0.031(5) Uiso 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 O2 1.4455(11) . ?
S1 O3 1.4295(12) . ?
S1 N2 1.6413(13) . ?
S1 N3 1.6433(13) . ?
S2 O1 1.4438(11) . ?
S2 O4 1.4296(12) . ?
S2 N1 1.6303(12) . ?
S2 N4 1.6423(13) . ?
N1 C7 1.4707(18) . ?
N1 C21 1.4759(18) . ?
N2 C23 1.4746(18) . ?
N2 C37 1.4833(19) . ?
N3 C15 1.4858(19) . ?
N3 H3 0.85(2) . ?
N4 C19 1.4830(19) . ?
N4 H4 0.83(2) . ?
C1 C3 1.398(2) . ?
C1 C5 1.5080(19) . ?
C1 C20 1.390(2) . ?
C2 C8 1.388(2) . ?
C2 C12 1.398(2) . ?
C2 C19 1.5120(19) . ?
C3 H3A 0.9500 . ?
C3 C28 1.392(2) . ?
C4 C16 1.391(2) . ?
C4 C18 1.397(2) . ?
C4 C21 1.508(2) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C5 C7 1.5386(19) . ?
C6 H6 0.9500 . ?
C6 C11 1.386(2) . ?
C6 C33 1.389(2) . ?
C7 H7 1.0000 . ?
C7 C19 1.5549(18) . ?
C8 H8 0.9500 . ?
C8 C31 1.387(2) . ?
C9 H9 0.9500 . ?
C9 C11 1.393(2) . ?
C9 C17 1.390(2) . ?
C10 H10 0.9500 . ?
C10 C12 1.386(2) . ?
C10 C24 1.387(2) . ?
C11 C15 1.5131(19) . ?
C12 H12 0.9500 . ?
C13 C22 1.394(2) . ?
C13 C25 1.391(2) . ?
C13 C30 1.510(2) . ?
C14 H14 0.9500 . ?
C14 C17 1.383(2) . ?
C14 C33 1.389(2) . ?
C15 H15 1.0000 . ?
C15 C23 1.5571(19) . ?
C16 H16 0.9500 . ?
C16 C27 1.394(2) . ?
C17 H17 0.9500 . ?
C18 H18 0.9500 . ?
C18 C34 1.383(2) . ?
C19 H19 1.0000 . ?
C20 H20 0.9500 . ?
C20 C32 1.397(2) . ?
C21 H21A 0.9900 . ?
C21 H21B 0.9900 . ?
C22 H22 0.9500 . ?
C22 C40 1.388(2) . ?
C23 H23 1.0000 . ?
C23 C30 1.544(2) . ?
C24 H24 0.9500 . ?
C24 C31 1.391(2) . ?
C25 H25 0.9500 . ?
C25 C36 1.392(2) . ?
C26 C29 1.394(2) . ?
C26 C37 1.511(2) . ?
C26 C38 1.390(2) . ?
C27 H27 0.9500 . ?
C27 C39 1.377(2) . ?
C28 H28 0.9500 . ?
C28 C35 1.389(3) . ?
C29 H29 0.9500 . ?
C29 C43 1.388(3) . ?
C30 H30A 0.9900 . ?
C30 H30B 0.9900 . ?
C31 H31 0.9500 . ?
C32 H32 0.9500 . ?
C32 C35 1.383(3) . ?
C33 H33 0.9500 . ?
C34 H34 0.9500 . ?
C34 C39 1.392(2) . ?
C35 H35 0.9500 . ?
C36 H36 0.9500 . ?
C36 C41 1.384(3) . ?
C37 H37A 0.9900 . ?
C37 H37B 0.9900 . ?
C38 H38 0.9500 . ?
C38 C42 1.392(3) . ?
C39 H39 0.9500 . ?
C40 H40 0.9500 . ?
C40 C41 1.381(3) . ?
C41 H41 0.9500 . ?
C42 H42 0.9500 . ?
C42 C44 1.380(3) . ?
C43 H43 0.9500 . ?
C43 C44 1.379(3) . ?
C44 H44 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
O2 S1 N2 113.29(7) . . ?
O2 S1 N3 109.14(7) . . ?
O3 S1 O2 115.16(7) . . ?
O3 S1 N2 108.98(7) . . ?
O3 S1 N3 112.65(7) . . ?
N2 S1 N3 96.10(6) . . ?
O1 S2 N1 113.98(7) . . ?
O1 S2 N4 108.68(7) . . ?
O4 S2 O1 114.59(7) . . ?
O4 S2 N1 108.91(7) . . ?
O4 S2 N4 113.16(7) . . ?
N1 S2 N4 96.15(6) . . ?
C7 N1 S2 112.78(9) . . ?
C7 N1 C21 120.15(11) . . ?
C21 N1 S2 116.93(10) . . ?
C23 N2 S1 111.47(9) . . ?
C23 N2 C37 120.65(12) . . ?
C37 N2 S1 114.89(10) . . ?
S1 N3 H3 108.3(13) . . ?
C15 N3 S1 111.36(10) . . ?
C15 N3 H3 111.2(13) . . ?
S2 N4 H4 109.4(14) . . ?
C19 N4 S2 111.08(9) . . ?
C19 N4 H4 110.2(14) . . ?
C3 C1 C5 119.55(13) . . ?
C20 C1 C3 118.76(14) . . ?
C20 C1 C5 121.60(13) . . ?
C8 C2 C12 119.40(14) . . ?
C8 C2 C19 123.51(13) . . ?
C12 C2 C19 117.09(13) . . ?
C1 C3 H3A 119.6 . . ?
C28 C3 C1 120.76(14) . . ?
C28 C3 H3A 119.6 . . ?
C16 C4 C18 118.99(14) . . ?
C16 C4 C21 120.32(13) . . ?
C18 C4 C21 120.68(13) . . ?
C1 C5 H5A 109.9 . . ?
C1 C5 H5B 109.9 . . ?
C1 C5 C7 109.14(11) . . ?
H5A C5 H5B 108.3 . . ?
C7 C5 H5A 109.9 . . ?
C7 C5 H5B 109.9 . . ?
C11 C6 H6 119.8 . . ?
C11 C6 C33 120.48(14) . . ?
C33 C6 H6 119.8 . . ?
N1 C7 C5 115.50(11) . . ?
N1 C7 H7 108.6 . . ?
N1 C7 C19 102.78(11) . . ?
C5 C7 H7 108.6 . . ?
C5 C7 C19 112.50(11) . . ?
C19 C7 H7 108.6 . . ?
C2 C8 H8 119.9 . . ?
C31 C8 C2 120.11(15) . . ?
C31 C8 H8 119.9 . . ?
C11 C9 H9 119.7 . . ?
C17 C9 H9 119.7 . . ?
C17 C9 C11 120.54(13) . . ?
C12 C10 H10 119.9 . . ?
C12 C10 C24 120.24(15) . . ?
C24 C10 H10 119.9 . . ?
C6 C11 C9 118.90(13) . . ?
C6 C11 C15 123.05(13) . . ?
C9 C11 C15 118.04(13) . . ?
C2 C12 H12 119.9 . . ?
C10 C12 C2 120.26(14) . . ?
C10 C12 H12 119.9 . . ?
C22 C13 C30 119.38(14) . . ?
C25 C13 C22 118.48(15) . . ?
C25 C13 C30 121.89(14) . . ?
C17 C14 H14 120.3 . . ?
C17 C14 C33 119.37(14) . . ?
C33 C14 H14 120.3 . . ?
N3 C15 C11 113.27(12) . . ?
N3 C15 H15 107.9 . . ?
N3 C15 C23 106.03(11) . . ?
C11 C15 H15 107.9 . . ?
C11 C15 C23 113.69(11) . . ?
C23 C15 H15 107.9 . . ?
C4 C16 H16 119.7 . . ?
C4 C16 C27 120.66(14) . . ?
C27 C16 H16 119.7 . . ?
C9 C17 H17 119.9 . . ?
C14 C17 C9 120.27(14) . . ?
C14 C17 H17 119.9 . . ?
C4 C18 H18 119.9 . . ?
C34 C18 C4 120.19(14) . . ?
C34 C18 H18 119.9 . . ?
N4 C19 C2 113.20(12) . . ?
N4 C19 C7 106.52(11) . . ?
N4 C19 H19 108.1 . . ?
C2 C19 C7 112.72(11) . . ?
C2 C19 H19 108.1 . . ?
C7 C19 H19 108.1 . . ?
C1 C20 H20 119.8 . . ?
C1 C20 C32 120.50(15) . . ?
C32 C20 H20 119.8 . . ?
N1 C21 C4 110.34(12) . . ?
N1 C21 H21A 109.6 . . ?
N1 C21 H21B 109.6 . . ?
C4 C21 H21A 109.6 . . ?
C4 C21 H21B 109.6 . . ?
H21A C21 H21B 108.1 . . ?
C13 C22 H22 119.7 . . ?
C40 C22 C13 120.61(15) . . ?
C40 C22 H22 119.7 . . ?
N2 C23 C15 102.93(11) . . ?
N2 C23 H23 108.6 . . ?
N2 C23 C30 116.20(12) . . ?
C15 C23 H23 108.6 . . ?
C30 C23 C15 111.58(11) . . ?
C30 C23 H23 108.6 . . ?
C10 C24 H24 120.2 . . ?
C10 C24 C31 119.54(14) . . ?
C31 C24 H24 120.2 . . ?
C13 C25 H25 119.6 . . ?
C13 C25 C36 120.76(15) . . ?
C36 C25 H25 119.6 . . ?
C29 C26 C37 120.86(14) . . ?
C38 C26 C29 118.83(15) . . ?
C38 C26 C37 120.31(15) . . ?
C16 C27 H27 120.1 . . ?
C39 C27 C16 119.78(15) . . ?
C39 C27 H27 120.1 . . ?
C3 C28 H28 120.1 . . ?
C35 C28 C3 119.88(15) . . ?
C35 C28 H28 120.1 . . ?
C26 C29 H29 120.0 . . ?
C43 C29 C26 120.07(16) . . ?
C43 C29 H29 120.0 . . ?
C13 C30 C23 108.33(12) . . ?
C13 C30 H30A 110.0 . . ?
C13 C30 H30B 110.0 . . ?
C23 C30 H30A 110.0 . . ?
C23 C30 H30B 110.0 . . ?
H30A C30 H30B 108.4 . . ?
C8 C31 C24 120.44(15) . . ?
C8 C31 H31 119.8 . . ?
C24 C31 H31 119.8 . . ?
C20 C32 H32 119.9 . . ?
C35 C32 C20 120.18(15) . . ?
C35 C32 H32 119.9 . . ?
C6 C33 H33 119.8 . . ?
C14 C33 C6 120.39(14) . . ?
C14 C33 H33 119.8 . . ?
C18 C34 H34 119.9 . . ?
C18 C34 C39 120.28(15) . . ?
C39 C34 H34 119.9 . . ?
C28 C35 H35 120.0 . . ?
C32 C35 C28 119.92(15) . . ?
C32 C35 H35 120.0 . . ?
C25 C36 H36 120.0 . . ?
C41 C36 C25 120.07(16) . . ?
C41 C36 H36 120.0 . . ?
N2 C37 C26 111.58(12) . . ?
N2 C37 H37A 109.3 . . ?
N2 C37 H37B 109.3 . . ?
C26 C37 H37A 109.3 . . ?
C26 C37 H37B 109.3 . . ?
H37A C37 H37B 108.0 . . ?
C26 C38 H38 119.7 . . ?
C26 C38 C42 120.67(16) . . ?
C42 C38 H38 119.7 . . ?
C27 C39 C34 120.09(15) . . ?
C27 C39 H39 120.0 . . ?
C34 C39 H39 120.0 . . ?
C22 C40 H40 119.8 . . ?
C41 C40 C22 120.43(16) . . ?
C41 C40 H40 119.8 . . ?
C36 C41 H41 120.2 . . ?
C40 C41 C36 119.66(16) . . ?
C40 C41 H41 120.2 . . ?
C38 C42 H42 120.0 . . ?
C44 C42 C38 119.96(16) . . ?
C44 C42 H42 120.0 . . ?
C29 C43 H43 119.6 . . ?
C44 C43 C29 120.71(17) . . ?
C44 C43 H43 119.6 . . ?
C42 C44 H44 120.1 . . ?
C43 C44 C42 119.73(17) . . ?
C43 C44 H44 120.1 . . ?

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
S1 N2 C23 C15 34.42(13) . . . . ?
S1 N2 C23 C30 -87.82(13) . . . . ?
S1 N2 C37 C26 -175.13(10) . . . . ?
S1 N3 C15 C11 -103.90(12) . . . . ?
S1 N3 C15 C23 21.45(14) . . . . ?
S2 N1 C7 C5 91.52(12) . . . . ?
S2 N1 C7 C19 -31.36(13) . . . . ?
S2 N1 C21 C4 164.81(10) . . . . ?
S2 N4 C19 C2 101.98(12) . . . . ?
S2 N4 C19 C7 -22.46(13) . . . . ?
O1 S2 N1 C7 -96.03(10) . . . . ?
O1 S2 N1 C21 49.48(12) . . . . ?
O1 S2 N4 C19 121.87(10) . . . . ?
O2 S1 N2 C23 93.07(10) . . . . ?
O2 S1 N2 C37 -48.79(13) . . . . ?
O2 S1 N3 C15 -118.75(10) . . . . ?
O3 S1 N2 C23 -137.33(10) . . . . ?
O3 S1 N2 C37 80.82(12) . . . . ?
O3 S1 N3 C15 112.03(10) . . . . ?
O4 S2 N1 C7 134.64(10) . . . . ?
O4 S2 N1 C21 -79.84(12) . . . . ?
O4 S2 N4 C19 -109.65(10) . . . . ?
N1 S2 N4 C19 3.97(11) . . . . ?
N1 C7 C19 N4 32.29(13) . . . . ?
N1 C7 C19 C2 -92.44(13) . . . . ?
N2 S1 N3 C15 -1.49(11) . . . . ?
N2 C23 C30 C13 -162.59(12) . . . . ?
N3 S1 N2 C23 -20.82(11) . . . . ?
N3 S1 N2 C37 -162.67(11) . . . . ?
N3 C15 C23 N2 -33.68(14) . . . . ?
N3 C15 C23 C30 91.62(13) . . . . ?
N4 S2 N1 C7 17.57(10) . . . . ?
N4 S2 N1 C21 163.09(11) . . . . ?
C1 C3 C28 C35 -0.1(2) . . . . ?
C1 C5 C7 N1 165.23(11) . . . . ?
C1 C5 C7 C19 -77.20(14) . . . . ?
C1 C20 C32 C35 -0.2(2) . . . . ?
C2 C8 C31 C24 -1.0(2) . . . . ?
C3 C1 C5 C7 -77.20(15) . . . . ?
C3 C1 C20 C32 0.2(2) . . . . ?
C3 C28 C35 C32 0.0(2) . . . . ?
C4 C16 C27 C39 0.4(2) . . . . ?
C4 C18 C34 C39 0.1(2) . . . . ?
C5 C1 C3 C28 176.67(13) . . . . ?
C5 C1 C20 C32 -176.45(13) . . . . ?
C5 C7 C19 N4 -92.59(13) . . . . ?
C5 C7 C19 C2 142.69(12) . . . . ?
C6 C11 C15 N3 27.81(19) . . . . ?
C6 C11 C15 C23 -93.32(16) . . . . ?
C7 N1 C21 C4 -52.32(17) . . . . ?
C8 C2 C12 C10 -0.5(2) . . . . ?
C8 C2 C19 N4 -20.12(19) . . . . ?
C8 C2 C19 C7 100.87(16) . . . . ?
C9 C11 C15 N3 -152.95(12) . . . . ?
C9 C11 C15 C23 85.92(15) . . . . ?
C10 C24 C31 C8 0.4(2) . . . . ?
C11 C6 C33 C14 1.6(2) . . . . ?
C11 C9 C17 C14 0.9(2) . . . . ?
C11 C15 C23 N2 91.42(13) . . . . ?
C11 C15 C23 C30 -143.28(12) . . . . ?
C12 C2 C8 C31 1.0(2) . . . . ?
C12 C2 C19 N4 160.39(12) . . . . ?
C12 C2 C19 C7 -78.62(15) . . . . ?
C12 C10 C24 C31 0.1(2) . . . . ?
C13 C22 C40 C41 0.0(2) . . . . ?
C13 C25 C36 C41 0.9(2) . . . . ?
C15 C23 C30 C13 79.84(14) . . . . ?
C16 C4 C18 C34 0.0(2) . . . . ?
C16 C4 C21 N1 125.23(14) . . . . ?
C16 C27 C39 C34 -0.4(2) . . . . ?
C17 C9 C11 C6 0.9(2) . . . . ?
C17 C9 C11 C15 -178.36(13) . . . . ?
C17 C14 C33 C6 0.2(2) . . . . ?
C18 C4 C16 C27 -0.2(2) . . . . ?
C18 C4 C21 N1 -53.43(18) . . . . ?
C18 C34 C39 C27 0.2(2) . . . . ?
C19 C2 C8 C31 -178.48(13) . . . . ?
C19 C2 C12 C10 179.04(13) . . . . ?
C20 C1 C3 C28 0.0(2) . . . . ?
C20 C1 C5 C7 99.39(15) . . . . ?
C20 C32 C35 C28 0.1(2) . . . . ?
C21 N1 C7 C5 -52.76(17) . . . . ?
C21 N1 C7 C19 -175.65(12) . . . . ?
C21 C4 C16 C27 -178.87(13) . . . . ?
C21 C4 C18 C34 178.64(13) . . . . ?
C22 C13 C25 C36 -0.7(2) . . . . ?
C22 C13 C30 C23 80.80(16) . . . . ?
C22 C40 C41 C36 0.3(3) . . . . ?
C23 N2 C37 C26 46.80(18) . . . . ?
C24 C10 C12 C2 -0.1(2) . . . . ?
C25 C13 C22 C40 0.2(2) . . . . ?
C25 C13 C30 C23 -93.32(16) . . . . ?
C25 C36 C41 C40 -0.7(2) . . . . ?
C26 C29 C43 C44 0.0(3) . . . . ?
C26 C38 C42 C44 -0.5(3) . . . . ?
C29 C26 C37 N2 58.51(19) . . . . ?
C29 C26 C38 C42 -1.0(2) . . . . ?
C29 C43 C44 C42 -1.5(3) . . . . ?
C30 C13 C22 C40 -174.10(14) . . . . ?
C30 C13 C25 C36 173.50(14) . . . . ?
C33 C6 C11 C9 -2.2(2) . . . . ?
C33 C6 C11 C15 177.05(14) . . . . ?
C33 C14 C17 C9 -1.5(2) . . . . ?
C37 N2 C23 C15 173.78(12) . . . . ?
C37 N2 C23 C30 51.54(18) . . . . ?
C37 C26 C29 C43 -178.50(15) . . . . ?
C37 C26 C38 C42 178.78(15) . . . . ?
C38 C26 C29 C43 1.3(2) . . . . ?
C38 C26 C37 N2 -121.25(16) . . . . ?
C38 C42 C44 C43 1.8(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
