# Electronic Supplementary Material (ESI) for Chemical Communications.
# This journal is © The Royal Society of Chemistry 2020

####################################################################### 
# 
# 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_mo_d8v20037_0m
_database_code_depnum_ccdc_archive 'CCDC 2006747'
loop_
_audit_author_name
_audit_author_address
'Ali Wang'
;Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences
China
;
_audit_update_record             
;
2020-05-30 deposited with the CCDC.	2020-11-16 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C16 H11 N O2'
_chemical_formula_weight         249.26

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'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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, -z'

_cell_length_a                   6.0435(5)
_cell_length_b                   7.9580(6)
_cell_length_c                   13.3572(11)
_cell_angle_alpha                75.360(2)
_cell_angle_beta                 83.114(2)
_cell_angle_gamma                77.584(2)
_cell_volume                     605.55(8)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    8226
_cell_measurement_theta_min      6.324
_cell_measurement_theta_max      54.777

_exptl_crystal_description       prismatic
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.367
_exptl_crystal_F_000             260
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.160
_exptl_crystal_size_min          0.120
_exptl_absorpt_coefficient_mu    0.091
_shelx_estimated_absorpt_T_min   0.982
_shelx_estimated_absorpt_T_max   0.989
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6214
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            14855
_diffrn_reflns_av_unetI/netI     0.0225
_diffrn_reflns_av_R_equivalents  0.0379
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.696
_diffrn_reflns_theta_max         25.999
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measured_fraction_theta_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_point_group_measured_fraction_full 0.991
_reflns_number_total             2364
_reflns_number_gt                2051
_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.0590P)²+0.0906P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2364
_refine_ls_number_parameters     176
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0447
_refine_ls_R_factor_gt           0.0389
_refine_ls_wR_factor_ref         0.1117
_refine_ls_wR_factor_gt          0.1049
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_restrained_S_all      1.043
_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
O1 O 0.77969(16) 0.68437(12) 0.49504(7) 0.0563(3) Uani 1 1 d . . . . .
O2 O 0.15896(15) 0.19653(13) 0.78383(9) 0.0653(3) Uani 1 1 d . . . . .
N1 N 0.78792(18) 0.41354(14) 0.60248(8) 0.0448(3) Uani 1 1 d . . . . .
C1 C 0.6823(2) 0.58409(16) 0.56354(9) 0.0432(3) Uani 1 1 d . . . . .
C2 C 0.4534(2) 0.63606(15) 0.60902(9) 0.0418(3) Uani 1 1 d . . . . .
C3 C 0.3408(2) 0.81099(17) 0.57534(10) 0.0527(3) Uani 1 1 d . . . . .
H3 H 0.4113 0.8897 0.5246 0.063 Uiso 1 1 calc R U . . .
C4 C 0.1277(3) 0.86718(18) 0.61647(11) 0.0590(4) Uani 1 1 d . . . . .
H4 H 0.0535 0.9838 0.5940 0.071 Uiso 1 1 calc R U . . .
C5 C 0.0230(2) 0.74927(19) 0.69188(11) 0.0557(4) Uani 1 1 d . . . . .
H5 H -0.1215 0.7880 0.7202 0.067 Uiso 1 1 calc R U . . .
C6 C 0.1288(2) 0.57643(17) 0.72549(10) 0.0482(3) Uani 1 1 d . . . . .
H6 H 0.0552 0.4997 0.7762 0.058 Uiso 1 1 calc R U . . .
C7 C 0.3475(2) 0.51385(15) 0.68416(9) 0.0400(3) Uani 1 1 d . . . . .
C8 C 0.47173(19) 0.33268(15) 0.71565(9) 0.0399(3) Uani 1 1 d . . . . .
C9 C 0.6869(2) 0.29353(16) 0.67391(9) 0.0421(3) Uani 1 1 d . . . . .
H9 H 0.7693 0.1792 0.6952 0.050 Uiso 1 1 calc R U . . .
C10 C 0.36361(19) 0.18672(16) 0.77902(10) 0.0436(3) Uani 1 1 d . . . . .
C11 C 0.50602(19) 0.01961(16) 0.83657(9) 0.0415(3) Uani 1 1 d . . . . .
C12 C 0.4328(2) -0.13796(18) 0.84514(11) 0.0524(3) Uani 1 1 d . . . . .
H12 H 0.3055 -0.1374 0.8122 0.063 Uiso 1 1 calc R U . . .
C13 C 0.5480(3) -0.2949(2) 0.90218(13) 0.0647(4) Uani 1 1 d . . . . .
H13 H 0.5007 -0.4002 0.9061 0.078 Uiso 1 1 calc R U . . .
C14 C 0.7335(3) -0.2959(2) 0.95352(12) 0.0659(4) Uani 1 1 d . . . . .
H14 H 0.8089 -0.4015 0.9934 0.079 Uiso 1 1 calc R U . . .
C15 C 0.8068(2) -0.1408(2) 0.94571(11) 0.0592(4) Uani 1 1 d . . . . .
H15 H 0.9320 -0.1419 0.9803 0.071 Uiso 1 1 calc R U . . .
C16 C 0.6954(2) 0.01676(17) 0.88678(10) 0.0473(3) Uani 1 1 d . . . . .
H16 H 0.7474 0.1209 0.8808 0.057 Uiso 1 1 calc R U . . .
H1 H 0.934(3) 0.3809(19) 0.5736(11) 0.055(4) 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
O1 C1 1.2345(14) . ?
O2 C10 1.2173(14) . ?
N1 C9 1.3584(15) . ?
N1 C1 1.3675(16) . ?
N1 H1 0.932(16) . ?
C1 C2 1.4606(17) . ?
C2 C3 1.3976(17) . ?
C2 C7 1.4083(16) . ?
C3 C4 1.366(2) . ?
C3 H3 0.9300 . ?
C4 C5 1.386(2) . ?
C4 H4 0.9300 . ?
C5 C6 1.3714(19) . ?
C5 H5 0.9300 . ?
C6 C7 1.4073(17) . ?
C6 H6 0.9300 . ?
C7 C8 1.4571(17) . ?
C8 C9 1.3562(17) . ?
C8 C10 1.4797(16) . ?
C9 H9 0.9300 . ?
C10 C11 1.4999(16) . ?
C11 C16 1.3877(17) . ?
C11 C12 1.3910(18) . ?
C12 C13 1.377(2) . ?
C12 H12 0.9300 . ?
C13 C14 1.380(2) . ?
C13 H13 0.9300 . ?
C14 C15 1.374(2) . ?
C14 H14 0.9300 . ?
C15 C16 1.3822(19) . ?
C15 H15 0.9300 . ?
C16 H16 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C9 N1 C1 123.76(11) . . ?
C9 N1 H1 120.8(9) . . ?
C1 N1 H1 115.4(9) . . ?
O1 C1 N1 120.64(11) . . ?
O1 C1 C2 123.80(11) . . ?
N1 C1 C2 115.55(10) . . ?
C3 C2 C7 120.62(12) . . ?
C3 C2 C1 118.10(11) . . ?
C7 C2 C1 121.28(11) . . ?
C4 C3 C2 120.47(13) . . ?
C4 C3 H3 119.8 . . ?
C2 C3 H3 119.8 . . ?
C3 C4 C5 119.56(12) . . ?
C3 C4 H4 120.2 . . ?
C5 C4 H4 120.2 . . ?
C6 C5 C4 121.14(13) . . ?
C6 C5 H5 119.4 . . ?
C4 C5 H5 119.4 . . ?
C5 C6 C7 120.76(13) . . ?
C5 C6 H6 119.6 . . ?
C7 C6 H6 119.6 . . ?
C6 C7 C2 117.43(11) . . ?
C6 C7 C8 124.22(11) . . ?
C2 C7 C8 118.34(11) . . ?
C9 C8 C7 117.85(10) . . ?
C9 C8 C10 118.85(11) . . ?
C7 C8 C10 122.75(10) . . ?
C8 C9 N1 123.07(11) . . ?
C8 C9 H9 118.5 . . ?
N1 C9 H9 118.5 . . ?
O2 C10 C8 121.35(11) . . ?
O2 C10 C11 118.26(10) . . ?
C8 C10 C11 120.36(10) . . ?
C16 C11 C12 119.16(11) . . ?
C16 C11 C10 123.34(11) . . ?
C12 C11 C10 117.34(11) . . ?
C13 C12 C11 120.34(13) . . ?
C13 C12 H12 119.8 . . ?
C11 C12 H12 119.8 . . ?
C12 C13 C14 120.07(14) . . ?
C12 C13 H13 120.0 . . ?
C14 C13 H13 120.0 . . ?
C15 C14 C13 119.99(13) . . ?
C15 C14 H14 120.0 . . ?
C13 C14 H14 120.0 . . ?
C14 C15 C16 120.36(13) . . ?
C14 C15 H15 119.8 . . ?
C16 C15 H15 119.8 . . ?
C15 C16 C11 120.04(13) . . ?
C15 C16 H16 120.0 . . ?
C11 C16 H16 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
C9 N1 C1 O1 -176.49(11) . . . . ?
C9 N1 C1 C2 4.03(17) . . . . ?
O1 C1 C2 C3 -2.08(18) . . . . ?
N1 C1 C2 C3 177.39(11) . . . . ?
O1 C1 C2 C7 177.49(11) . . . . ?
N1 C1 C2 C7 -3.05(17) . . . . ?
C7 C2 C3 C4 1.4(2) . . . . ?
C1 C2 C3 C4 -179.02(12) . . . . ?
C2 C3 C4 C5 -0.2(2) . . . . ?
C3 C4 C5 C6 -0.5(2) . . . . ?
C4 C5 C6 C7 0.0(2) . . . . ?
C5 C6 C7 C2 1.18(18) . . . . ?
C5 C6 C7 C8 179.89(12) . . . . ?
C3 C2 C7 C6 -1.87(18) . . . . ?
C1 C2 C7 C6 178.58(10) . . . . ?
C3 C2 C7 C8 179.35(10) . . . . ?
C1 C2 C7 C8 -0.21(17) . . . . ?
C6 C7 C8 C9 -175.96(12) . . . . ?
C2 C7 C8 C9 2.74(17) . . . . ?
C6 C7 C8 C10 12.59(18) . . . . ?
C2 C7 C8 C10 -168.71(11) . . . . ?
C7 C8 C9 N1 -2.00(18) . . . . ?
C10 C8 C9 N1 169.79(11) . . . . ?
C1 N1 C9 C8 -1.58(19) . . . . ?
C9 C8 C10 O2 -150.33(13) . . . . ?
C7 C8 C10 O2 21.03(19) . . . . ?
C9 C8 C10 C11 27.71(17) . . . . ?
C7 C8 C10 C11 -160.93(11) . . . . ?
O2 C10 C11 C16 -142.59(13) . . . . ?
C8 C10 C11 C16 39.31(17) . . . . ?
O2 C10 C11 C12 32.90(18) . . . . ?
C8 C10 C11 C12 -145.21(12) . . . . ?
C16 C11 C12 C13 -0.4(2) . . . . ?
C10 C11 C12 C13 -176.12(13) . . . . ?
C11 C12 C13 C14 1.7(2) . . . . ?
C12 C13 C14 C15 -1.6(2) . . . . ?
C13 C14 C15 C16 0.1(2) . . . . ?
C14 C15 C16 C11 1.1(2) . . . . ?
C12 C11 C16 C15 -0.99(19) . . . . ?
C10 C11 C16 C15 174.42(12) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H1 O1 0.932(16) 1.890(16) 2.8202(14) 175.4(13) 2_766
N1 H1 O1 0.932(16) 1.890(16) 2.8202(14) 175.4(13) 2_766
N1 H1 O1 0.932(16) 1.890(16) 2.8202(14) 175.4(13) 2_766

_refine_diff_density_max         0.189
_refine_diff_density_min         -0.142
_refine_diff_density_rms         0.029

_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_d8v20091
_database_code_depnum_ccdc_archive 'CCDC 2006748'
loop_
_audit_author_name
_audit_author_address
'Ali Wang'
;Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences
China
;
_audit_update_record             
;
2020-05-30 deposited with the CCDC.	2020-11-16 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C17 H13 N O2'
_chemical_formula_weight         263.28

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_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+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   15.5206(7)
_cell_length_b                   10.7027(4)
_cell_length_c                   7.9095(3)
_cell_angle_alpha                90
_cell_angle_beta                 90.7410(10)
_cell_angle_gamma                90
_cell_volume                     1313.76(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    8214
_cell_measurement_theta_min      4.623
_cell_measurement_theta_max      54.527

_exptl_crystal_description       prismatic
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.331
_exptl_crystal_F_000             552
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.190
_exptl_crystal_size_mid          0.170
_exptl_crystal_size_min          0.110
_exptl_absorpt_coefficient_mu    0.088
_shelx_estimated_absorpt_T_min   0.984
_shelx_estimated_absorpt_T_max   0.990
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.4402
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            18845
_diffrn_reflns_av_unetI/netI     0.0396
_diffrn_reflns_av_R_equivalents  0.0705
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         3.203
_diffrn_reflns_theta_max         25.999
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 0.993
_reflns_number_total             2568
_reflns_number_gt                2054
_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.0569P)²+0.2794P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.078(10)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2568
_refine_ls_number_parameters     183
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0561
_refine_ls_R_factor_gt           0.0447
_refine_ls_wR_factor_ref         0.1264
_refine_ls_wR_factor_gt          0.1166
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_restrained_S_all      1.035
_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_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
O1 O 0.80447(8) 0.43834(12) 0.3554(2) 0.0806(5) Uani 1 1 d . . . . .
O2 O 0.81518(8) 1.02398(10) 0.28696(17) 0.0623(4) Uani 1 1 d . . . . .
N1 N 0.72488(8) 0.86384(12) 0.35840(16) 0.0475(3) Uani 1 1 d . . . . .
C1 C 0.79705(10) 0.90188(14) 0.29247(19) 0.0462(4) Uani 1 1 d . . . . .
C2 C 0.86172(9) 0.82178(14) 0.22423(18) 0.0432(4) Uani 1 1 d . . . . .
C3 C 0.93796(10) 0.86994(16) 0.1538(2) 0.0532(4) Uani 1 1 d . . . . .
H3 H 0.9461 0.9559 0.1466 0.064 Uiso 1 1 calc R U . . .
C4 C 0.99973(10) 0.79039(18) 0.0962(2) 0.0584(5) Uani 1 1 d . . . . .
H4 H 1.0503 0.8219 0.0509 0.070 Uiso 1 1 calc R U . . .
C5 C 0.98683(10) 0.66207(17) 0.1055(2) 0.0572(4) Uani 1 1 d . . . . .
H5 H 1.0293 0.6085 0.0660 0.069 Uiso 1 1 calc R U . . .
C6 C 0.91321(10) 0.61267(15) 0.1712(2) 0.0508(4) Uani 1 1 d . . . . .
H6 H 0.9059 0.5265 0.1746 0.061 Uiso 1 1 calc R U . . .
C7 C 0.84818(9) 0.69182(14) 0.23416(18) 0.0415(4) Uani 1 1 d . . . . .
C8 C 0.76825(9) 0.64954(14) 0.30483(18) 0.0425(4) Uani 1 1 d . . . . .
C9 C 0.71199(10) 0.73830(14) 0.3610(2) 0.0461(4) Uani 1 1 d . . . . .
H9 H 0.6602 0.7101 0.4049 0.055 Uiso 1 1 calc R U . . .
C10 C 0.74807(10) 0.51581(14) 0.3310(2) 0.0499(4) Uani 1 1 d . . . . .
C11 C 0.65570(10) 0.47266(13) 0.33068(19) 0.0457(4) Uani 1 1 d . . . . .
C12 C 0.63385(12) 0.37460(15) 0.4358(2) 0.0569(5) Uani 1 1 d . . . . .
H12 H 0.6755 0.3390 0.5064 0.068 Uiso 1 1 calc R U . . .
C13 C 0.55003(14) 0.32917(17) 0.4364(3) 0.0680(6) Uani 1 1 d . . . . .
H13 H 0.5355 0.2636 0.5077 0.082 Uiso 1 1 calc R U . . .
C14 C 0.48856(12) 0.38115(18) 0.3317(2) 0.0657(5) Uani 1 1 d . . . . .
H14 H 0.4323 0.3513 0.3331 0.079 Uiso 1 1 calc R U . . .
C15 C 0.50980(11) 0.47656(17) 0.2255(2) 0.0599(5) Uani 1 1 d . . . . .
H15 H 0.4681 0.5107 0.1538 0.072 Uiso 1 1 calc R U . . .
C16 C 0.59321(10) 0.52288(15) 0.2239(2) 0.0513(4) Uani 1 1 d . . . . .
H16 H 0.6073 0.5878 0.1511 0.062 Uiso 1 1 calc R U . . .
C17 C 0.75595(13) 1.10922(16) 0.3634(3) 0.0714(6) Uani 1 1 d . . . . .
H17A H 0.6995 1.0973 0.3150 0.107 Uiso 1 1 calc R U . . .
H17B H 0.7745 1.1935 0.3435 0.107 Uiso 1 1 calc R U . . .
H17C H 0.7542 1.0940 0.4829 0.107 Uiso 1 1 calc R U . . .


_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
O1 C10 1.2192(19) . ?
O2 C1 1.3375(18) . ?
O2 C17 1.434(2) . ?
N1 C1 1.3068(19) . ?
N1 C9 1.3586(19) . ?
C1 C2 1.431(2) . ?
C2 C7 1.409(2) . ?
C2 C3 1.412(2) . ?
C3 C4 1.365(2) . ?
C3 H3 0.9300 . ?
C4 C5 1.390(3) . ?
C4 H4 0.9300 . ?
C5 C6 1.368(2) . ?
C5 H5 0.9300 . ?
C6 C7 1.413(2) . ?
C6 H6 0.9300 . ?
C7 C8 1.440(2) . ?
C8 C9 1.368(2) . ?
C8 C10 1.480(2) . ?
C9 H9 0.9300 . ?
C10 C11 1.506(2) . ?
C11 C12 1.384(2) . ?
C11 C16 1.386(2) . ?
C12 C13 1.389(3) . ?
C12 H12 0.9300 . ?
C13 C14 1.373(3) . ?
C13 H13 0.9300 . ?
C14 C15 1.365(3) . ?
C14 H14 0.9300 . ?
C15 C16 1.386(2) . ?
C15 H15 0.9300 . ?
C16 H16 0.9300 . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?

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
C1 O2 C17 118.13(13) . . ?
C1 N1 C9 116.18(13) . . ?
N1 C1 O2 119.94(14) . . ?
N1 C1 C2 124.95(14) . . ?
O2 C1 C2 115.10(13) . . ?
C7 C2 C3 120.58(14) . . ?
C7 C2 C1 117.68(13) . . ?
C3 C2 C1 121.71(14) . . ?
C4 C3 C2 119.99(16) . . ?
C4 C3 H3 120.0 . . ?
C2 C3 H3 120.0 . . ?
C3 C4 C5 119.76(15) . . ?
C3 C4 H4 120.1 . . ?
C5 C4 H4 120.1 . . ?
C6 C5 C4 121.58(15) . . ?
C6 C5 H5 119.2 . . ?
C4 C5 H5 119.2 . . ?
C5 C6 C7 120.40(15) . . ?
C5 C6 H6 119.8 . . ?
C7 C6 H6 119.8 . . ?
C2 C7 C6 117.67(14) . . ?
C2 C7 C8 117.49(13) . . ?
C6 C7 C8 124.82(14) . . ?
C9 C8 C7 117.67(14) . . ?
C9 C8 C10 119.26(13) . . ?
C7 C8 C10 122.89(13) . . ?
N1 C9 C8 125.95(14) . . ?
N1 C9 H9 117.0 . . ?
C8 C9 H9 117.0 . . ?
O1 C10 C8 121.80(14) . . ?
O1 C10 C11 118.24(14) . . ?
C8 C10 C11 119.95(13) . . ?
C12 C11 C16 119.02(15) . . ?
C12 C11 C10 118.16(15) . . ?
C16 C11 C10 122.73(14) . . ?
C11 C12 C13 120.28(17) . . ?
C11 C12 H12 119.9 . . ?
C13 C12 H12 119.9 . . ?
C14 C13 C12 119.98(17) . . ?
C14 C13 H13 120.0 . . ?
C12 C13 H13 120.0 . . ?
C15 C14 C13 120.17(16) . . ?
C15 C14 H14 119.9 . . ?
C13 C14 H14 119.9 . . ?
C14 C15 C16 120.40(18) . . ?
C14 C15 H15 119.8 . . ?
C16 C15 H15 119.8 . . ?
C11 C16 C15 120.13(16) . . ?
C11 C16 H16 119.9 . . ?
C15 C16 H16 119.9 . . ?
O2 C17 H17A 109.5 . . ?
O2 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
O2 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?

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
C9 N1 C1 O2 -179.19(13) . . . . ?
C9 N1 C1 C2 0.1(2) . . . . ?
C17 O2 C1 N1 3.5(2) . . . . ?
C17 O2 C1 C2 -175.88(15) . . . . ?
N1 C1 C2 C7 -2.4(2) . . . . ?
O2 C1 C2 C7 176.92(13) . . . . ?
N1 C1 C2 C3 179.51(15) . . . . ?
O2 C1 C2 C3 -1.2(2) . . . . ?
C7 C2 C3 C4 -0.7(2) . . . . ?
C1 C2 C3 C4 177.33(15) . . . . ?
C2 C3 C4 C5 0.7(3) . . . . ?
C3 C4 C5 C6 0.0(3) . . . . ?
C4 C5 C6 C7 -0.8(2) . . . . ?
C3 C2 C7 C6 -0.1(2) . . . . ?
C1 C2 C7 C6 -178.19(13) . . . . ?
C3 C2 C7 C8 -178.93(13) . . . . ?
C1 C2 C7 C8 3.0(2) . . . . ?
C5 C6 C7 C2 0.8(2) . . . . ?
C5 C6 C7 C8 179.59(14) . . . . ?
C2 C7 C8 C9 -1.5(2) . . . . ?
C6 C7 C8 C9 179.75(14) . . . . ?
C2 C7 C8 C10 -176.57(13) . . . . ?
C6 C7 C8 C10 4.7(2) . . . . ?
C1 N1 C9 C8 1.6(2) . . . . ?
C7 C8 C9 N1 -0.9(2) . . . . ?
C10 C8 C9 N1 174.35(14) . . . . ?
C9 C8 C10 O1 -147.17(17) . . . . ?
C7 C8 C10 O1 27.8(2) . . . . ?
C9 C8 C10 C11 31.9(2) . . . . ?
C7 C8 C10 C11 -153.16(14) . . . . ?
O1 C10 C11 C12 32.7(2) . . . . ?
C8 C10 C11 C12 -146.32(15) . . . . ?
O1 C10 C11 C16 -144.00(17) . . . . ?
C8 C10 C11 C16 36.9(2) . . . . ?
C16 C11 C12 C13 -1.3(2) . . . . ?
C10 C11 C12 C13 -178.17(15) . . . . ?
C11 C12 C13 C14 0.4(3) . . . . ?
C12 C13 C14 C15 0.7(3) . . . . ?
C13 C14 C15 C16 -0.8(3) . . . . ?
C12 C11 C16 C15 1.2(2) . . . . ?
C10 C11 C16 C15 177.91(14) . . . . ?
C14 C15 C16 C11 -0.2(3) . . . . ?

_refine_diff_density_max         0.143
_refine_diff_density_min         -0.177
_refine_diff_density_rms         0.032

_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_mo_d8v20111_0m
_database_code_depnum_ccdc_archive 'CCDC 2006749'
loop_
_audit_author_name
_audit_author_address
'Ali Wang'
;Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences
China
;
_audit_update_record             
;
2020-05-30 deposited with the CCDC.	2020-11-16 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C15 H11 N O3 S'
_chemical_formula_weight         285.31

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

_space_group_crystal_system      orthorhombic
_space_group_IT_number           29
_space_group_name_H-M_alt        'P c a 21'
_space_group_name_Hall           'P 2c -2ac'

_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, z+1/2'
'x+1/2, -y, z'
'-x+1/2, y, z+1/2'

_cell_length_a                   16.2100(8)
_cell_length_b                   5.4630(3)
_cell_length_c                   30.5412(19)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2704.6(3)
_cell_formula_units_Z            8
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    9160
_cell_measurement_theta_min      5.200
_cell_measurement_theta_max      54.637

_exptl_crystal_description       prismatic
_exptl_crystal_colour            red
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.401
_exptl_crystal_F_000             1184
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.1800
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.130
_exptl_absorpt_coefficient_mu    0.245
_shelx_estimated_absorpt_T_min   0.710
_shelx_estimated_absorpt_T_max   0.969
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6370
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            22708
_diffrn_reflns_av_unetI/netI     0.0304
_diffrn_reflns_av_R_equivalents  0.0349
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -34
_diffrn_reflns_limit_l_max       37
_diffrn_reflns_theta_min         2.600
_diffrn_reflns_theta_max         25.998
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.971
_diffrn_reflns_point_group_measured_fraction_full 0.978
_reflns_number_total             5161
_reflns_number_gt                4324
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.915
_reflns_Friedel_fraction_max     0.947
_reflns_Friedel_fraction_full    0.962

_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    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.1096P)²+0.6048P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.020(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 
; 
 Flack x determined using 1793 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons and Flack (2004), Acta Cryst. A60, s61). 
;
_refine_ls_abs_structure_Flack   0.04(3)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         5161
_refine_ls_number_parameters     367
_refine_ls_number_restraints     5
_refine_ls_R_factor_all          0.0658
_refine_ls_R_factor_gt           0.0549
_refine_ls_wR_factor_ref         0.1718
_refine_ls_wR_factor_gt          0.1571
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_restrained_S_all      1.057
_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 0.63086(10) 0.3650(3) 0.68417(6) 0.0738(5) Uani 1 1 d D . . . .
S2 S 0.47493(12) 0.1319(4) 0.31245(6) 0.0845(6) Uani 1 1 d D . . . .
O1 O 0.6271(2) 0.0387(8) 0.61374(15) 0.0679(11) Uani 1 1 d . . . . .
O2 O 0.5842(3) -0.1902(9) 0.54756(15) 0.0742(12) Uani 1 1 d . . . . .
H2 H 0.6025 -0.2086 0.5724 0.111 Uiso 1 1 calc R U . . .
O3 O 0.3731(2) 0.0593(7) 0.63977(14) 0.0559(9) Uani 1 1 d . . . . .
N1 N 0.3241(4) 0.4464(13) 0.7227(2) 0.0867(18) Uani 1 1 d . . . . .
C1 C 0.5933(4) 0.6170(11) 0.7075(2) 0.0642(15) Uani 1 1 d . . . . .
H1 H 0.6165 0.6890 0.7322 0.077 Uiso 1 1 calc R U . . .
C2 C 0.5264(4) 0.7057(11) 0.6872(2) 0.0679(16) Uani 1 1 d . . . . .
H2A H 0.4996 0.8457 0.6970 0.081 Uiso 1 1 calc R U . . .
C3 C 0.4975(3) 0.5701(7) 0.64840(16) 0.0424(10) Uani 1 1 d D . . . .
H3 H 0.4534 0.6066 0.6301 0.051 Uiso 1 1 calc R U . . .
C4 C 0.5557(3) 0.3618(8) 0.64555(17) 0.0464(11) Uani 1 1 d D . . . .
C5 C 0.5616(3) 0.1652(9) 0.61290(18) 0.0490(11) Uani 1 1 d . . . . .
C6 C 0.5000(3) 0.1182(9) 0.57999(17) 0.0462(11) Uani 1 1 d . . . . .
C7 C 0.5179(3) -0.0584(11) 0.54914(19) 0.0572(13) Uani 1 1 d . . . . .
H7 H 0.4787 -0.0854 0.5275 0.069 Uiso 1 1 calc R U . . .
C8 C 0.4209(3) 0.2519(9) 0.57584(17) 0.0451(10) Uani 1 1 d . . . . .
C9 C 0.4081(4) 0.4105(10) 0.54144(19) 0.0601(14) Uani 1 1 d . . . . .
H9 H 0.4490 0.4284 0.5203 0.072 Uiso 1 1 calc R U . . .
C10 C 0.3359(4) 0.5437(13) 0.5375(2) 0.0720(17) Uani 1 1 d . . . . .
H10 H 0.3292 0.6514 0.5142 0.086 Uiso 1 1 calc R U . . .
C11 C 0.2746(4) 0.5179(12) 0.5677(2) 0.0728(18) Uani 1 1 d . . . . .
H11 H 0.2262 0.6083 0.5652 0.087 Uiso 1 1 calc R U . . .
C12 C 0.2847(3) 0.3552(10) 0.6024(2) 0.0603(14) Uani 1 1 d . . . . .
H12 H 0.2427 0.3356 0.6228 0.072 Uiso 1 1 calc R U . . .
C13 C 0.3570(3) 0.2225(9) 0.60668(18) 0.0482(12) Uani 1 1 d . . . . .
C14 C 0.3160(3) 0.0490(11) 0.6761(2) 0.0654(16) Uani 1 1 d . . . . .
H14A H 0.2604 0.0274 0.6650 0.079 Uiso 1 1 calc R U . . .
H14B H 0.3292 -0.0909 0.6943 0.079 Uiso 1 1 calc R U . . .
C15 C 0.3196(3) 0.2689(13) 0.7021(2) 0.0634(15) Uani 1 1 d . . . . .
O4 O 0.4710(2) 0.4506(8) 0.38520(14) 0.0630(10) Uani 1 1 d . . . . .
O5 O 0.5116(3) 0.6757(9) 0.45189(15) 0.0735(12) Uani 1 1 d . . . . .
H5 H 0.4826 0.6389 0.4309 0.110 Uiso 1 1 calc R U . . .
O6 O 0.7234(2) 0.4282(7) 0.36085(12) 0.0551(9) Uani 1 1 d . . . . .
N2 N 0.7836(4) 0.0599(13) 0.2769(2) 0.0864(18) Uani 1 1 d . . . . .
C16 C 0.5128(4) -0.1233(12) 0.2904(2) 0.0700(17) Uani 1 1 d . . . . .
H16 H 0.4920 -0.1935 0.2650 0.084 Uiso 1 1 calc R U . . .
C17 C 0.5764(4) -0.2180(10) 0.3130(2) 0.0605(13) Uani 1 1 d . . . . .
H17 H 0.6032 -0.3603 0.3042 0.073 Uiso 1 1 calc R U . . .
C18 C 0.6008(3) -0.0850(8) 0.35196(15) 0.0396(9) Uani 1 1 d D . . . .
H18 H 0.6428 -0.1251 0.3714 0.048 Uiso 1 1 calc R U . . .
C19 C 0.5446(3) 0.1283(9) 0.35418(16) 0.0444(11) Uani 1 1 d D . . . .
C20 C 0.5370(3) 0.3205(9) 0.38655(18) 0.0465(11) Uani 1 1 d . . . . .
C21 C 0.5960(3) 0.3689(9) 0.42013(16) 0.0459(11) Uani 1 1 d . . . . .
C22 C 0.5788(4) 0.5437(11) 0.4513(2) 0.0585(13) Uani 1 1 d . . . . .
H22 H 0.616(4) 0.561(11) 0.483(2) 0.070 Uiso 1 1 d . U . . .
C23 C 0.6762(3) 0.2348(9) 0.42448(15) 0.0433(10) Uani 1 1 d . . . . .
C24 C 0.6894(4) 0.0773(10) 0.45937(18) 0.0573(13) Uani 1 1 d . . . . .
H24 H 0.6481 0.0563 0.4802 0.069 Uiso 1 1 calc R U . . .
C25 C 0.7623(4) -0.0481(12) 0.4637(2) 0.0719(17) Uani 1 1 d . . . . .
H25 H 0.7695 -0.1534 0.4873 0.086 Uiso 1 1 calc R U . . .
C26 C 0.8228(4) -0.0210(12) 0.4345(2) 0.0708(17) Uani 1 1 d . . . . .
H26 H 0.8720 -0.1064 0.4381 0.085 Uiso 1 1 calc R U . . .
C27 C 0.8128(3) 0.1364(10) 0.3982(2) 0.0593(14) Uani 1 1 d . . . . .
H27 H 0.8543 0.1524 0.3774 0.071 Uiso 1 1 calc R U . . .
C28 C 0.7404(3) 0.2652(9) 0.39448(17) 0.0459(11) Uani 1 1 d . . . . .
C29 C 0.7819(4) 0.4479(11) 0.3267(2) 0.0618(15) Uani 1 1 d . . . . .
H29A H 0.8364 0.4696 0.3393 0.074 Uiso 1 1 calc R U . . .
H29B H 0.7696 0.5917 0.3093 0.074 Uiso 1 1 calc R U . . .
C30 C 0.7825(4) 0.2306(13) 0.2981(2) 0.0615(15) 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 C1 1.666(6) . ?
S1 C4 1.696(5) . ?
S2 C16 1.665(7) . ?
S2 C19 1.703(5) . ?
O1 C5 1.267(6) . ?
O2 C7 1.294(7) . ?
O2 H2 0.8200 . ?
O3 C13 1.373(6) . ?
O3 C14 1.444(7) . ?
N1 C15 1.159(9) . ?
C1 C2 1.341(9) . ?
C1 H1 0.9300 . ?
C2 C3 1.473(7) . ?
C2 H2A 0.9300 . ?
C3 C4 1.481(6) . ?
C3 H3 0.9300 . ?
C4 C5 1.468(7) . ?
C5 C6 1.440(7) . ?
C6 C7 1.380(7) . ?
C6 C8 1.481(7) . ?
C7 H7 0.9300 . ?
C8 C9 1.378(8) . ?
C8 C13 1.409(7) . ?
C9 C10 1.383(9) . ?
C9 H9 0.9300 . ?
C10 C11 1.363(10) . ?
C10 H10 0.9300 . ?
C11 C12 1.392(9) . ?
C11 H11 0.9300 . ?
C12 C13 1.384(8) . ?
C12 H12 0.9300 . ?
C14 C15 1.441(10) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
O4 C20 1.284(6) . ?
O5 C22 1.306(7) . ?
O5 H5 0.8200 . ?
O6 C28 1.387(6) . ?
O6 C29 1.413(7) . ?
N2 C30 1.136(9) . ?
C16 C17 1.344(9) . ?
C16 H16 0.9300 . ?
C17 C18 1.448(7) . ?
C17 H17 0.9300 . ?
C18 C19 1.480(7) . ?
C18 H18 0.9300 . ?
C19 C20 1.447(7) . ?
C20 C21 1.428(7) . ?
C21 C22 1.377(7) . ?
C21 C23 1.499(7) . ?
C22 H22 1.15(7) . ?
C23 C24 1.386(7) . ?
C23 C28 1.395(7) . ?
C24 C25 1.372(9) . ?
C24 H24 0.9300 . ?
C25 C26 1.334(10) . ?
C25 H25 0.9300 . ?
C26 C27 1.412(9) . ?
C26 H26 0.9300 . ?
C27 C28 1.374(8) . ?
C27 H27 0.9300 . ?
C29 C30 1.474(10) . ?
C29 H29A 0.9700 . ?
C29 H29B 0.9700 . ?

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
C1 S1 C4 92.5(3) . . ?
C16 S2 C19 92.8(3) . . ?
C7 O2 H2 109.5 . . ?
C13 O3 C14 118.0(4) . . ?
C2 C1 S1 113.3(5) . . ?
C2 C1 H1 123.4 . . ?
S1 C1 H1 123.4 . . ?
C1 C2 C3 116.6(5) . . ?
C1 C2 H2A 121.7 . . ?
C3 C2 H2A 121.7 . . ?
C2 C3 C4 103.4(4) . . ?
C2 C3 H3 128.3 . . ?
C4 C3 H3 128.3 . . ?
C5 C4 C3 130.0(4) . . ?
C5 C4 S1 115.7(4) . . ?
C3 C4 S1 114.1(3) . . ?
O1 C5 C6 119.9(5) . . ?
O1 C5 C4 116.1(5) . . ?
C6 C5 C4 124.0(4) . . ?
C7 C6 C5 117.1(5) . . ?
C7 C6 C8 118.0(5) . . ?
C5 C6 C8 124.9(4) . . ?
O2 C7 C6 126.1(5) . . ?
O2 C7 H7 116.9 . . ?
C6 C7 H7 116.9 . . ?
C9 C8 C13 118.1(5) . . ?
C9 C8 C6 120.4(5) . . ?
C13 C8 C6 121.5(5) . . ?
C8 C9 C10 121.6(6) . . ?
C8 C9 H9 119.2 . . ?
C10 C9 H9 119.2 . . ?
C11 C10 C9 120.3(6) . . ?
C11 C10 H10 119.9 . . ?
C9 C10 H10 119.9 . . ?
C10 C11 C12 119.6(6) . . ?
C10 C11 H11 120.2 . . ?
C12 C11 H11 120.2 . . ?
C13 C12 C11 120.4(6) . . ?
C13 C12 H12 119.8 . . ?
C11 C12 H12 119.8 . . ?
O3 C13 C12 124.7(5) . . ?
O3 C13 C8 115.3(4) . . ?
C12 C13 C8 120.0(5) . . ?
C15 C14 O3 111.4(5) . . ?
C15 C14 H14A 109.3 . . ?
O3 C14 H14A 109.3 . . ?
C15 C14 H14B 109.3 . . ?
O3 C14 H14B 109.3 . . ?
H14A C14 H14B 108.0 . . ?
N1 C15 C14 178.6(7) . . ?
C22 O5 H5 109.5 . . ?
C28 O6 C29 117.5(4) . . ?
C17 C16 S2 113.4(5) . . ?
C17 C16 H16 123.3 . . ?
S2 C16 H16 123.3 . . ?
C16 C17 C18 116.0(5) . . ?
C16 C17 H17 122.0 . . ?
C18 C17 H17 122.0 . . ?
C17 C18 C19 105.3(4) . . ?
C17 C18 H18 127.3 . . ?
C19 C18 H18 127.3 . . ?
C20 C19 C18 130.9(4) . . ?
C20 C19 S2 116.5(4) . . ?
C18 C19 S2 112.5(3) . . ?
O4 C20 C21 118.6(5) . . ?
O4 C20 C19 116.8(5) . . ?
C21 C20 C19 124.6(4) . . ?
C22 C21 C20 119.3(5) . . ?
C22 C21 C23 117.0(5) . . ?
C20 C21 C23 123.7(4) . . ?
O5 C22 C21 124.1(6) . . ?
O5 C22 H22 112(3) . . ?
C21 C22 H22 123(3) . . ?
C24 C23 C28 117.7(5) . . ?
C24 C23 C21 120.3(4) . . ?
C28 C23 C21 122.0(4) . . ?
C25 C24 C23 121.1(6) . . ?
C25 C24 H24 119.5 . . ?
C23 C24 H24 119.5 . . ?
C26 C25 C24 120.9(6) . . ?
C26 C25 H25 119.5 . . ?
C24 C25 H25 119.5 . . ?
C25 C26 C27 120.5(6) . . ?
C25 C26 H26 119.8 . . ?
C27 C26 H26 119.8 . . ?
C28 C27 C26 118.4(5) . . ?
C28 C27 H27 120.8 . . ?
C26 C27 H27 120.8 . . ?
C27 C28 O6 124.1(5) . . ?
C27 C28 C23 121.4(5) . . ?
O6 C28 C23 114.5(4) . . ?
O6 C29 C30 112.3(5) . . ?
O6 C29 H29A 109.1 . . ?
C30 C29 H29A 109.1 . . ?
O6 C29 H29B 109.1 . . ?
C30 C29 H29B 109.1 . . ?
H29A C29 H29B 107.9 . . ?
N2 C30 C29 178.3(7) . . ?

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
C4 S1 C1 C2 -1.2(6) . . . . ?
S1 C1 C2 C3 0.0(8) . . . . ?
C1 C2 C3 C4 1.5(7) . . . . ?
C2 C3 C4 C5 -177.4(5) . . . . ?
C2 C3 C4 S1 -2.3(5) . . . . ?
C1 S1 C4 C5 178.0(4) . . . . ?
C1 S1 C4 C3 2.1(4) . . . . ?
C3 C4 C5 O1 166.6(5) . . . . ?
S1 C4 C5 O1 -8.4(6) . . . . ?
C3 C4 C5 C6 -10.8(8) . . . . ?
S1 C4 C5 C6 174.2(4) . . . . ?
O1 C5 C6 C7 -3.1(8) . . . . ?
C4 C5 C6 C7 174.1(5) . . . . ?
O1 C5 C6 C8 179.5(5) . . . . ?
C4 C5 C6 C8 -3.2(8) . . . . ?
C5 C6 C7 O2 1.7(8) . . . . ?
C8 C6 C7 O2 179.2(6) . . . . ?
C7 C6 C8 C9 -67.9(6) . . . . ?
C5 C6 C8 C9 109.4(6) . . . . ?
C7 C6 C8 C13 112.4(5) . . . . ?
C5 C6 C8 C13 -70.3(7) . . . . ?
C13 C8 C9 C10 1.9(8) . . . . ?
C6 C8 C9 C10 -177.9(5) . . . . ?
C8 C9 C10 C11 -1.0(10) . . . . ?
C9 C10 C11 C12 -0.4(10) . . . . ?
C10 C11 C12 C13 0.9(9) . . . . ?
C14 O3 C13 C12 -9.1(7) . . . . ?
C14 O3 C13 C8 170.4(5) . . . . ?
C11 C12 C13 O3 179.6(5) . . . . ?
C11 C12 C13 C8 0.1(8) . . . . ?
C9 C8 C13 O3 179.0(4) . . . . ?
C6 C8 C13 O3 -1.2(7) . . . . ?
C9 C8 C13 C12 -1.4(7) . . . . ?
C6 C8 C13 C12 178.3(5) . . . . ?
C13 O3 C14 C15 -68.7(6) . . . . ?
C19 S2 C16 C17 0.5(6) . . . . ?
S2 C16 C17 C18 0.1(8) . . . . ?
C16 C17 C18 C19 -0.7(7) . . . . ?
C17 C18 C19 C20 177.2(5) . . . . ?
C17 C18 C19 S2 1.0(5) . . . . ?
C16 S2 C19 C20 -177.7(4) . . . . ?
C16 S2 C19 C18 -0.9(4) . . . . ?
C18 C19 C20 O4 -164.8(5) . . . . ?
S2 C19 C20 O4 11.3(6) . . . . ?
C18 C19 C20 C21 13.3(8) . . . . ?
S2 C19 C20 C21 -170.6(4) . . . . ?
O4 C20 C21 C22 3.4(8) . . . . ?
C19 C20 C21 C22 -174.6(5) . . . . ?
O4 C20 C21 C23 -178.3(5) . . . . ?
C19 C20 C21 C23 3.7(8) . . . . ?
C20 C21 C22 O5 -1.7(9) . . . . ?
C23 C21 C22 O5 179.9(5) . . . . ?
C22 C21 C23 C24 67.1(7) . . . . ?
C20 C21 C23 C24 -111.2(6) . . . . ?
C22 C21 C23 C28 -111.9(6) . . . . ?
C20 C21 C23 C28 69.8(7) . . . . ?
C28 C23 C24 C25 -1.4(8) . . . . ?
C21 C23 C24 C25 179.6(5) . . . . ?
C23 C24 C25 C26 0.3(10) . . . . ?
C24 C25 C26 C27 -0.5(10) . . . . ?
C25 C26 C27 C28 1.8(9) . . . . ?
C26 C27 C28 O6 179.0(5) . . . . ?
C26 C27 C28 C23 -2.9(8) . . . . ?
C29 O6 C28 C27 4.9(8) . . . . ?
C29 O6 C28 C23 -173.3(5) . . . . ?
C24 C23 C28 C27 2.7(7) . . . . ?
C21 C23 C28 C27 -178.3(5) . . . . ?
C24 C23 C28 O6 -179.0(4) . . . . ?
C21 C23 C28 O6 0.0(7) . . . . ?
C28 O6 C29 C30 72.0(6) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C29 H29A O4 0.97 2.63 3.590(7) 170.6 3_565
C22 H22 O2 1.15(7) 2.44(6) 3.280(7) 128(4) 1_565
O5 H5 O4 0.82 1.75 2.469(6) 146.2 .
C14 H14B N1 0.97 2.67 3.590(9) 157.6 1_545
C1 H1 S2 0.93 3.03 3.657(7) 126.6 2_665
O2 H2 O1 0.82 1.89 2.476(6) 127.3 .

_refine_diff_density_max         0.354
_refine_diff_density_min         -0.330
_refine_diff_density_rms         0.057

_shelxl_version_number           2013-4

