# Electronic Supplementary Material (ESI) for ChemComm.
# 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_150830_0m
_database_code_depnum_ccdc_archive 'CCDC 1469306'
_audit_update_record             
;
2016-03-18 deposited with the CCDC.
2016-08-22 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C14 H12 N2 O2'
_chemical_formula_weight         240.26

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                   6.0661(4)
_cell_length_b                   7.8841(5)
_cell_length_c                   12.8564(8)
_cell_angle_alpha                91.070(4)
_cell_angle_beta                 94.098(4)
_cell_angle_gamma                97.330(3)
_cell_volume                     608.04(7)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    3367
_cell_measurement_theta_min      3.0140
_cell_measurement_theta_max      24.1809

_exptl_crystal_description       Lump
_exptl_crystal_colour            Colorless
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.312
_exptl_crystal_F_000             252
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.15
_exptl_absorpt_coefficient_mu    0.090
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8740
_exptl_absorpt_correction_T_max  0.9485
_exptl_absorpt_process_details   'SADABS V2014/4 (Bruker AXS Inc.)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(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 8.3333
_diffrn_reflns_number            8386
_diffrn_reflns_av_unetI/netI     0.0254
_diffrn_reflns_av_R_equivalents  0.0249
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         1.589
_diffrn_reflns_theta_max         26.404
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.967
_diffrn_measured_fraction_theta_full 0.971
_diffrn_reflns_Laue_measured_fraction_max 0.967
_diffrn_reflns_Laue_measured_fraction_full 0.971
_diffrn_reflns_point_group_measured_fraction_max 0.967
_diffrn_reflns_point_group_measured_fraction_full 0.971
_reflns_number_total             2424
_reflns_number_gt                1878
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'APEX2 (Bruker AXS, 2010)'
_computing_cell_refinement       'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_data_reduction        'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  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)+(0.0878P)²+0.0511P] 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     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2424
_refine_ls_number_parameters     164
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0609
_refine_ls_R_factor_gt           0.0460
_refine_ls_wR_factor_ref         0.1556
_refine_ls_wR_factor_gt          0.1350
_refine_ls_goodness_of_fit_ref   1.127
_refine_ls_restrained_S_all      1.127
_refine_ls_shift/su_max          0.022
_refine_ls_shift/su_mean         0.003

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 1.0234(2) 0.74985(16) 0.57601(10) 0.0612(4) Uani 1 1 d . . . . .
O2 O 1.2608(2) 0.55335(18) 0.57492(10) 0.0641(4) Uani 1 1 d . . . . .
N1 N 0.9560(2) 0.52280(17) 0.67188(10) 0.0443(4) Uani 1 1 d . . . . .
N2 N 0.9962(4) 0.1926(3) 1.07364(14) 0.0900(7) Uani 1 1 d . . . . .
C1 C 0.4036(3) 0.0056(3) 0.75129(16) 0.0633(5) Uani 1 1 d . . . . .
H1 H 0.2801 -0.0722 0.7635 0.076 Uiso 1 1 calc R U . . .
C2 C 0.5650(3) 0.0528(3) 0.83117(15) 0.0592(5) Uani 1 1 d . . . . .
H9 H 0.5527 0.0070 0.8970 0.071 Uiso 1 1 calc R U . . .
C3 C 0.7456(3) 0.1699(2) 0.81091(12) 0.0469(4) Uani 1 1 d . . . . .
C4 C 0.7668(3) 0.2352(2) 0.71167(12) 0.0432(4) Uani 1 1 d . . . . .
C5 C 0.9817(2) 0.3556(2) 0.71199(12) 0.0429(4) Uani 1 1 d . . . . .
H10 H 1.0831 0.3030 0.6690 0.052 Uiso 1 1 calc R U . . .
C6 C 0.7716(3) 0.6166(2) 0.69014(14) 0.0514(4) Uani 1 1 d . . . . .
H11 H 0.7729 0.6517 0.7629 0.062 Uiso 1 1 calc R U . . .
H12 H 0.6296 0.5498 0.6687 0.062 Uiso 1 1 calc R U . . .
C7 C 0.8191(3) 0.7677(3) 0.6220(2) 0.0736(6) Uani 1 1 d . . . . .
H2 H 0.6989 0.7694 0.5682 0.088 Uiso 1 1 calc R U . . .
H3 H 0.8338 0.8734 0.6632 0.088 Uiso 1 1 calc R U . . .
C8 C 1.0946(3) 0.6011(2) 0.60568(13) 0.0464(4) Uani 1 1 d . . . . .
C9 C 0.9395(3) 0.2499(2) 0.87826(12) 0.0494(4) Uani 1 1 d . . . . .
C10 C 1.0749(3) 0.3580(2) 0.82492(13) 0.0477(4) Uani 1 1 d . . . . .
C11 C 1.2870(3) 0.4620(3) 0.86159(17) 0.0652(6) Uani 1 1 d . . . . .
H4 H 1.3094 0.4557 0.9360 0.098 Uiso 1 1 calc R U . . .
H5 H 1.2818 0.5788 0.8430 0.098 Uiso 1 1 calc R U . . .
H6 H 1.4078 0.4190 0.8296 0.098 Uiso 1 1 calc R U . . .
C12 C 0.9731(4) 0.2173(3) 0.98670(14) 0.0614(5) Uani 1 1 d . . . . .
C13 C 0.4230(3) 0.0722(2) 0.65352(15) 0.0574(5) Uani 1 1 d . . . . .
H8 H 0.3119 0.0390 0.6008 0.069 Uiso 1 1 calc R U . . .
C14 C 0.6050(3) 0.1878(2) 0.63248(13) 0.0493(4) Uani 1 1 d . . . . .
H7 H 0.6175 0.2324 0.5664 0.059 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 C8 1.353(2) . ?
O1 C7 1.432(2) . ?
O2 C8 1.210(2) . ?
N1 C8 1.342(2) . ?
N1 C5 1.447(2) . ?
N1 C6 1.447(2) . ?
N2 C12 1.140(2) . ?
C1 C2 1.378(3) . ?
C1 C13 1.378(3) . ?
C1 H1 0.9300 . ?
C2 C3 1.383(3) . ?
C2 H9 0.9300 . ?
C3 C4 1.393(2) . ?
C3 C9 1.475(2) . ?
C4 C14 1.374(2) . ?
C4 C5 1.511(2) . ?
C5 C10 1.519(2) . ?
C5 H10 0.9800 . ?
C6 C7 1.503(3) . ?
C6 H11 0.9700 . ?
C6 H12 0.9700 . ?
C7 H2 0.9700 . ?
C7 H3 0.9700 . ?
C9 C10 1.339(2) . ?
C9 C12 1.428(2) . ?
C10 C11 1.476(3) . ?
C11 H4 0.9600 . ?
C11 H5 0.9600 . ?
C11 H6 0.9600 . ?
C13 C14 1.385(3) . ?
C13 H8 0.9300 . ?
C14 H7 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C8 O1 C7 109.30(14) . . ?
C8 N1 C5 122.41(13) . . ?
C8 N1 C6 112.63(14) . . ?
C5 N1 C6 124.74(13) . . ?
C2 C1 C13 120.85(17) . . ?
C2 C1 H1 119.6 . . ?
C13 C1 H1 119.6 . . ?
C1 C2 C3 118.26(17) . . ?
C1 C2 H9 120.9 . . ?
C3 C2 H9 120.9 . . ?
C2 C3 C4 120.85(16) . . ?
C2 C3 C9 131.86(16) . . ?
C4 C3 C9 107.29(15) . . ?
C14 C4 C3 120.53(16) . . ?
C14 C4 C5 130.31(14) . . ?
C3 C4 C5 109.16(14) . . ?
N1 C5 C4 114.38(12) . . ?
N1 C5 C10 114.31(13) . . ?
C4 C5 C10 103.30(13) . . ?
N1 C5 H10 108.2 . . ?
C4 C5 H10 108.2 . . ?
C10 C5 H10 108.2 . . ?
N1 C6 C7 101.34(14) . . ?
N1 C6 H11 111.5 . . ?
C7 C6 H11 111.5 . . ?
N1 C6 H12 111.5 . . ?
C7 C6 H12 111.5 . . ?
H11 C6 H12 109.3 . . ?
O1 C7 C6 106.88(15) . . ?
O1 C7 H2 110.3 . . ?
C6 C7 H2 110.3 . . ?
O1 C7 H3 110.3 . . ?
C6 C7 H3 110.3 . . ?
H2 C7 H3 108.6 . . ?
O2 C8 N1 127.86(17) . . ?
O2 C8 O1 122.39(16) . . ?
N1 C8 O1 109.75(15) . . ?
C10 C9 C12 125.14(17) . . ?
C10 C9 C3 111.27(15) . . ?
C12 C9 C3 123.58(17) . . ?
C9 C10 C11 129.00(17) . . ?
C9 C10 C5 108.91(14) . . ?
C11 C10 C5 122.05(16) . . ?
C10 C11 H4 109.5 . . ?
C10 C11 H5 109.5 . . ?
H4 C11 H5 109.5 . . ?
C10 C11 H6 109.5 . . ?
H4 C11 H6 109.5 . . ?
H5 C11 H6 109.5 . . ?
N2 C12 C9 178.7(2) . . ?
C1 C13 C14 121.10(18) . . ?
C1 C13 H8 119.5 . . ?
C14 C13 H8 119.5 . . ?
C4 C14 C13 118.39(16) . . ?
C4 C14 H7 120.8 . . ?
C13 C14 H7 120.8 . . ?

_refine_diff_density_max         0.311
_refine_diff_density_min         -0.307
_refine_diff_density_rms         0.122

_shelxl_version_number           2014/6

####################################################################### 
# 
# 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_151232_0m_a
_database_code_depnum_ccdc_archive 'CCDC 1469307'
_audit_update_record             
;
2016-03-18 deposited with the CCDC.
2016-08-22 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C16 H16 N2 O2'
_chemical_formula_weight         268.31

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'

_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                   9.2837(4)
_cell_length_b                   9.9699(4)
_cell_length_c                   9.9836(4)
_cell_angle_alpha                92.401(2)
_cell_angle_beta                 112.162(2)
_cell_angle_gamma                116.147(2)
_cell_volume                     743.75(6)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    4400
_cell_measurement_theta_min      2.2752
_cell_measurement_theta_max      25.5368

_exptl_crystal_description       Lump
_exptl_crystal_colour            Colorless
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.198
_exptl_crystal_F_000             284
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.15
_exptl_absorpt_coefficient_mu    0.080
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8826
_exptl_absorpt_correction_T_max  0.9485
_exptl_absorpt_process_details   'SADABS V2014/4 (Bruker AXS Inc.)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(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 8.3333
_diffrn_reflns_number            11208
_diffrn_reflns_av_unetI/netI     0.0209
_diffrn_reflns_av_R_equivalents  0.0236
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         2.275
_diffrn_reflns_theta_max         26.382
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 0.994
_reflns_number_total             3018
_reflns_number_gt                2503
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'APEX2 (Bruker AXS, 2010)'
_computing_cell_refinement       'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_data_reduction        'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  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)+(0.0963P)²+0.1107P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3018
_refine_ls_number_parameters     192
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0601
_refine_ls_R_factor_gt           0.0490
_refine_ls_wR_factor_ref         0.1634
_refine_ls_wR_factor_gt          0.1503
_refine_ls_goodness_of_fit_ref   1.091
_refine_ls_restrained_S_all      1.091
_refine_ls_shift/su_max          0.012
_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
C1 C 0.3032(2) 0.78198(18) 0.71695(19) 0.0460(4) Uani 1 1 d . . . . .
C2 C 0.3556(3) 0.7759(2) 0.9580(2) 0.0633(5) Uani 1 1 d . . . . .
H2A H 0.2628 0.6961 0.9768 0.076 Uiso 1 1 calc R U . . .
H2B H 0.4345 0.8609 1.0468 0.076 Uiso 1 1 calc R U . . .
C3 C 0.4588(3) 0.7131(3) 0.9176(2) 0.0602(5) Uani 1 1 d . . . . .
H3A H 0.5867 0.7778 0.9779 0.072 Uiso 1 1 calc R U . . .
H3B H 0.4231 0.6085 0.9286 0.072 Uiso 1 1 calc R U . . .
C4 C 0.46559(18) 0.66177(16) 0.66676(15) 0.0365(3) Uani 1 1 d . . . . .
H4 H 0.4195 0.6823 0.5688 0.044 Uiso 1 1 calc R U . . .
C5 C 0.3994(2) 0.49110(17) 0.64713(16) 0.0392(4) Uani 1 1 d . . . . .
C6 C 0.2230(2) 0.37343(19) 0.59078(18) 0.0495(4) Uani 1 1 d . . . . .
H6 H 0.1296 0.3953 0.5566 0.059 Uiso 1 1 calc R U . . .
C7 C 0.1892(3) 0.2244(2) 0.5865(2) 0.0585(5) Uani 1 1 d . . . . .
H7 H 0.0718 0.1446 0.5498 0.070 Uiso 1 1 calc R U . . .
C8 C 0.3278(3) 0.19128(19) 0.6363(2) 0.0598(5) Uani 1 1 d . . . . .
H8 H 0.3024 0.0897 0.6334 0.072 Uiso 1 1 calc R U . . .
C9 C 0.5031(3) 0.30720(19) 0.68999(19) 0.0510(4) Uani 1 1 d . . . . .
H9 H 0.5959 0.2846 0.7215 0.061 Uiso 1 1 calc R U . . .
C10 C 0.5379(2) 0.45864(17) 0.69598(16) 0.0397(4) Uani 1 1 d . . . . .
C11 C 0.7175(2) 0.60549(17) 0.75413(16) 0.0397(4) Uani 1 1 d . . . . .
H11 H 0.7799 0.6022 0.6948 0.048 Uiso 1 1 calc R U . . .
C12 C 0.66884(19) 0.73320(16) 0.73007(15) 0.0371(3) Uani 1 1 d . . . . .
C13 C 0.7835(2) 0.88115(18) 0.75131(18) 0.0437(4) Uani 1 1 d . . . . .
C14 C 0.9812(2) 0.9415(2) 0.8102(2) 0.0584(5) Uani 1 1 d . . . . .
H14A H 1.0051 0.8572 0.8201 0.088 Uiso 1 1 calc R U . . .
H14B H 1.0427 1.0131 0.9060 0.088 Uiso 1 1 calc R U . . .
H14C H 1.0220 0.9930 0.7420 0.088 Uiso 1 1 calc R U . . .
C15 C 0.7234(3) 0.9986(2) 0.7156(2) 0.0587(5) Uani 1 1 d . . . . .
H15A H 0.5961 0.9466 0.6567 0.088 Uiso 1 1 calc R U . . .
H15B H 0.7808 1.0599 0.6606 0.088 Uiso 1 1 calc R U . . .
H15C H 0.7551 1.0642 0.8068 0.088 Uiso 1 1 calc R U . . .
C16 C 0.8267(2) 0.6224(2) 0.9119(2) 0.0540(5) Uani 1 1 d . . . . .
N1 N 0.9080(3) 0.6330(2) 1.0334(2) 0.0881(7) Uani 1 1 d . . . . .
N2 N 0.40782(16) 0.71771(14) 0.76286(14) 0.0403(3) Uani 1 1 d . . . . .
O1 O 0.24086(18) 0.80371(15) 0.59464(15) 0.0639(4) Uani 1 1 d . . . . .
O2 O 0.2783(2) 0.82776(17) 0.83162(16) 0.0681(4) Uani 1 1 d . . . . .
O3 O 0.0856(2) 0.5703(2) 0.31911(17) 0.0848(5) Uani 1 1 d . . . . .
H3C H 0.1433 0.6624 0.4130 0.080 Uiso 1 1 d . . . . .
H3D H 0.0221 0.6021 0.2323 0.080 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 O1 1.214(2) . ?
C1 N2 1.342(2) . ?
C1 O2 1.350(2) . ?
C2 O2 1.440(3) . ?
C2 C3 1.508(3) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C3 N2 1.444(2) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C4 N2 1.4582(19) . ?
C4 C5 1.507(2) . ?
C4 C12 1.531(2) . ?
C4 H4 0.9800 . ?
C5 C10 1.379(2) . ?
C5 C6 1.390(2) . ?
C6 C7 1.372(3) . ?
C6 H6 0.9300 . ?
C7 C8 1.385(3) . ?
C7 H7 0.9300 . ?
C8 C9 1.380(3) . ?
C8 H8 0.9300 . ?
C9 C10 1.391(2) . ?
C9 H9 0.9300 . ?
C10 C11 1.519(2) . ?
C11 C16 1.469(2) . ?
C11 C12 1.528(2) . ?
C11 H11 0.9800 . ?
C12 C13 1.332(2) . ?
C13 C14 1.503(2) . ?
C13 C15 1.506(2) . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C16 N1 1.132(2) . ?
O3 H3C 1.0601 . ?
O3 H3D 1.0006 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 C1 N2 128.19(16) . . ?
O1 C1 O2 122.08(15) . . ?
N2 C1 O2 109.70(14) . . ?
O2 C2 C3 105.95(15) . . ?
O2 C2 H2A 110.5 . . ?
C3 C2 H2A 110.5 . . ?
O2 C2 H2B 110.5 . . ?
C3 C2 H2B 110.5 . . ?
H2A C2 H2B 108.7 . . ?
N2 C3 C2 101.57(15) . . ?
N2 C3 H3A 111.5 . . ?
C2 C3 H3A 111.5 . . ?
N2 C3 H3B 111.5 . . ?
C2 C3 H3B 111.5 . . ?
H3A C3 H3B 109.3 . . ?
N2 C4 C5 111.43(11) . . ?
N2 C4 C12 113.83(11) . . ?
C5 C4 C12 103.80(12) . . ?
N2 C4 H4 109.2 . . ?
C5 C4 H4 109.2 . . ?
C12 C4 H4 109.2 . . ?
C10 C5 C6 120.71(15) . . ?
C10 C5 C4 112.09(13) . . ?
C6 C5 C4 127.18(14) . . ?
C7 C6 C5 118.71(17) . . ?
C7 C6 H6 120.6 . . ?
C5 C6 H6 120.6 . . ?
C6 C7 C8 120.79(17) . . ?
C6 C7 H7 119.6 . . ?
C8 C7 H7 119.6 . . ?
C9 C8 C7 120.82(16) . . ?
C9 C8 H8 119.6 . . ?
C7 C8 H8 119.6 . . ?
C8 C9 C10 118.52(17) . . ?
C8 C9 H9 120.7 . . ?
C10 C9 H9 120.7 . . ?
C5 C10 C9 120.44(15) . . ?
C5 C10 C11 111.01(13) . . ?
C9 C10 C11 128.54(15) . . ?
C16 C11 C10 109.92(13) . . ?
C16 C11 C12 113.04(13) . . ?
C10 C11 C12 103.98(12) . . ?
C16 C11 H11 109.9 . . ?
C10 C11 H11 109.9 . . ?
C12 C11 H11 109.9 . . ?
C13 C12 C11 125.41(14) . . ?
C13 C12 C4 125.42(14) . . ?
C11 C12 C4 109.02(11) . . ?
C12 C13 C14 122.19(15) . . ?
C12 C13 C15 122.26(15) . . ?
C14 C13 C15 115.54(15) . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C13 C15 H15A 109.5 . . ?
C13 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C13 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
N1 C16 C11 178.6(2) . . ?
C1 N2 C3 112.63(14) . . ?
C1 N2 C4 123.22(13) . . ?
C3 N2 C4 124.14(13) . . ?
C1 O2 C2 109.41(13) . . ?
H3C O3 H3D 104.7 . . ?

_refine_diff_density_max         0.387
_refine_diff_density_min         -0.399
_refine_diff_density_rms         0.141

_shelxl_version_number           2014/6

####################################################################### 
# 
# 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_150722LT_a
_database_code_depnum_ccdc_archive 'CCDC 1469309'
_audit_update_record             
;
2016-03-18 deposited with the CCDC.
2016-08-22 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C18 H16 N2 O2 S'
_chemical_formula_weight         324.39

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'
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'
H H 0.0000 0.0000 '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                   8.4209(5)
_cell_length_b                   28.5775(16)
_cell_length_c                   6.9049(4)
_cell_angle_alpha                90
_cell_angle_beta                 101.544(2)
_cell_angle_gamma                90
_cell_volume                     1628.04(16)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    6405
_cell_measurement_theta_min      2.8509
_cell_measurement_theta_max      26.4083

_exptl_crystal_description       Lump
_exptl_crystal_colour            Colorless
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.323
_exptl_crystal_F_000             680
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.12
_exptl_absorpt_coefficient_mu    0.210
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8991
_exptl_absorpt_correction_T_max  0.9485
_exptl_absorpt_process_details   'SADABS V2014/4 (Bruker AXS Inc.)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(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 8.3333
_diffrn_reflns_number            14968
_diffrn_reflns_av_unetI/netI     0.0248
_diffrn_reflns_av_R_equivalents  0.0276
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_k_max       35
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_limit_l_max       6
_diffrn_reflns_theta_min         1.425
_diffrn_reflns_theta_max         26.408
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             3346
_reflns_number_gt                3037
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'APEX2 (Bruker AXS, 2010)'
_computing_cell_refinement       'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_data_reduction        'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  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)+(0.0593P)²+0.5381P] 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     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3346
_refine_ls_number_parameters     210
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0405
_refine_ls_R_factor_gt           0.0341
_refine_ls_wR_factor_ref         0.1087
_refine_ls_wR_factor_gt          0.0965
_refine_ls_goodness_of_fit_ref   1.138
_refine_ls_restrained_S_all      1.138
_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
C1 C 0.45935(17) 0.61879(5) 0.5171(2) 0.0139(3) Uani 1 1 d . . . . .
H1 H 0.4247 0.5891 0.5734 0.017 Uiso 1 1 calc R U . . .
C2 C 0.32134(18) 0.65379(5) 0.4879(2) 0.0155(3) Uani 1 1 d . . . . .
C3 C 0.16957(19) 0.65137(6) 0.3664(2) 0.0196(3) Uani 1 1 d . . . . .
H3 H 0.1396 0.6254 0.2810 0.024 Uiso 1 1 calc R U . . .
C4 C 0.06161(19) 0.68822(6) 0.3730(2) 0.0219(4) Uani 1 1 d . . . . .
H4 H -0.0432 0.6873 0.2907 0.026 Uiso 1 1 calc R U . . .
C5 C 0.10538(19) 0.72620(6) 0.4984(2) 0.0213(3) Uani 1 1 d . . . . .
H5 H 0.0295 0.7506 0.5018 0.026 Uiso 1 1 calc R U . . .
C6 C 0.25922(19) 0.72890(5) 0.6191(2) 0.0180(3) Uani 1 1 d . . . . .
H6 H 0.2899 0.7549 0.7039 0.022 Uiso 1 1 calc R U . . .
C7 C 0.36568(18) 0.69229(5) 0.6113(2) 0.0146(3) Uani 1 1 d . . . . .
C8 C 0.53261(18) 0.68435(5) 0.7204(2) 0.0132(3) Uani 1 1 d . . . . .
C9 C 0.58965(17) 0.64269(5) 0.6705(2) 0.0133(3) Uani 1 1 d . . . . .
C10 C 0.74927(17) 0.62149(5) 0.7403(2) 0.0142(3) Uani 1 1 d . . . . .
C11 C 0.89011(18) 0.64852(5) 0.7747(2) 0.0185(3) Uani 1 1 d . . . . .
H11 H 0.8834 0.6814 0.7556 0.022 Uiso 1 1 calc R U . . .
C12 C 1.03987(19) 0.62737(6) 0.8367(2) 0.0241(4) Uani 1 1 d . . . . .
H12 H 1.1356 0.6459 0.8598 0.029 Uiso 1 1 calc R U . . .
C13 C 1.0506(2) 0.57932(6) 0.8651(2) 0.0265(4) Uani 1 1 d . . . . .
H13 H 1.1533 0.5650 0.9088 0.032 Uiso 1 1 calc R U . . .
C14 C 0.9111(2) 0.55228(6) 0.8296(3) 0.0246(4) Uani 1 1 d . . . . .
H14 H 0.9186 0.5193 0.8479 0.029 Uiso 1 1 calc R U . . .
C15 C 0.76142(19) 0.57298(5) 0.7679(2) 0.0181(3) Uani 1 1 d . . . . .
H15 H 0.6663 0.5542 0.7440 0.022 Uiso 1 1 calc R U . . .
C16 C 0.5811(2) 0.64745(5) 0.2359(2) 0.0220(3) Uani 1 1 d . . . . .
H16A H 0.4897 0.6658 0.1643 0.033 Uiso 1 1 calc R U . . .
H16B H 0.6445 0.6353 0.1424 0.033 Uiso 1 1 calc R U . . .
H16C H 0.6501 0.6674 0.3337 0.033 Uiso 1 1 calc R U . . .
C17 C 0.6754(2) 0.52863(6) 0.2742(3) 0.0252(4) Uani 1 1 d . . . . .
H17A H 0.7065 0.5223 0.4162 0.038 Uiso 1 1 calc R U . . .
H17B H 0.7587 0.5480 0.2328 0.038 Uiso 1 1 calc R U . . .
H17C H 0.6650 0.4990 0.2011 0.038 Uiso 1 1 calc R U . . .
C18 C 0.61946(17) 0.71637(5) 0.8626(2) 0.0146(3) Uani 1 1 d . . . . .
N1 N 0.51968(15) 0.60833(4) 0.33667(19) 0.0164(3) Uani 1 1 d . . . . .
N2 N 0.68849(17) 0.74199(5) 0.9777(2) 0.0201(3) Uani 1 1 d . . . . .
O1 O 0.45163(14) 0.56700(4) 0.01601(16) 0.0226(3) Uani 1 1 d . . . . .
O2 O 0.37585(14) 0.53283(4) 0.31428(18) 0.0252(3) Uani 1 1 d . . . . .
S1 S 0.48914(4) 0.55836(2) 0.22478(5) 0.01585(13) 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
C1 N1 1.4676(18) . ?
C1 C2 1.516(2) . ?
C1 C9 1.525(2) . ?
C1 H1 1.0000 . ?
C2 C3 1.383(2) . ?
C2 C7 1.396(2) . ?
C3 C4 1.398(2) . ?
C3 H3 0.9500 . ?
C4 C5 1.391(2) . ?
C4 H4 0.9500 . ?
C5 C6 1.395(2) . ?
C5 H5 0.9500 . ?
C6 C7 1.386(2) . ?
C6 H6 0.9500 . ?
C7 C8 1.473(2) . ?
C8 C9 1.354(2) . ?
C8 C18 1.431(2) . ?
C9 C10 1.465(2) . ?
C10 C11 1.395(2) . ?
C10 C15 1.400(2) . ?
C11 C12 1.387(2) . ?
C11 H11 0.9500 . ?
C12 C13 1.388(3) . ?
C12 H12 0.9500 . ?
C13 C14 1.386(2) . ?
C13 H13 0.9500 . ?
C14 C15 1.381(2) . ?
C14 H14 0.9500 . ?
C15 H15 0.9500 . ?
C16 N1 1.4646(18) . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C17 S1 1.7561(16) . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C18 N2 1.149(2) . ?
N1 S1 1.6195(12) . ?
O1 S1 1.4341(12) . ?
O2 S1 1.4352(12) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 C1 C2 114.07(12) . . ?
N1 C1 C9 110.95(11) . . ?
C2 C1 C9 102.87(11) . . ?
N1 C1 H1 109.6 . . ?
C2 C1 H1 109.6 . . ?
C9 C1 H1 109.6 . . ?
C3 C2 C7 120.76(14) . . ?
C3 C2 C1 129.69(14) . . ?
C7 C2 C1 109.54(13) . . ?
C2 C3 C4 118.09(15) . . ?
C2 C3 H3 121.0 . . ?
C4 C3 H3 121.0 . . ?
C5 C4 C3 120.98(15) . . ?
C5 C4 H4 119.5 . . ?
C3 C4 H4 119.5 . . ?
C4 C5 C6 120.91(14) . . ?
C4 C5 H5 119.5 . . ?
C6 C5 H5 119.5 . . ?
C7 C6 C5 117.73(14) . . ?
C7 C6 H6 121.1 . . ?
C5 C6 H6 121.1 . . ?
C6 C7 C2 121.52(14) . . ?
C6 C7 C8 130.89(14) . . ?
C2 C7 C8 107.58(13) . . ?
C9 C8 C18 125.31(14) . . ?
C9 C8 C7 110.86(13) . . ?
C18 C8 C7 123.81(13) . . ?
C8 C9 C10 128.97(13) . . ?
C8 C9 C1 109.13(12) . . ?
C10 C9 C1 121.88(12) . . ?
C11 C10 C15 119.24(14) . . ?
C11 C10 C9 121.31(13) . . ?
C15 C10 C9 119.43(13) . . ?
C12 C11 C10 120.06(14) . . ?
C12 C11 H11 120.0 . . ?
C10 C11 H11 120.0 . . ?
C11 C12 C13 120.29(15) . . ?
C11 C12 H12 119.9 . . ?
C13 C12 H12 119.9 . . ?
C14 C13 C12 119.86(15) . . ?
C14 C13 H13 120.1 . . ?
C12 C13 H13 120.1 . . ?
C15 C14 C13 120.31(15) . . ?
C15 C14 H14 119.8 . . ?
C13 C14 H14 119.8 . . ?
C14 C15 C10 120.24(15) . . ?
C14 C15 H15 119.9 . . ?
C10 C15 H15 119.9 . . ?
N1 C16 H16A 109.5 . . ?
N1 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
N1 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
S1 C17 H17A 109.5 . . ?
S1 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
S1 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
N2 C18 C8 179.52(16) . . ?
C16 N1 C1 117.56(11) . . ?
C16 N1 S1 118.95(10) . . ?
C1 N1 S1 122.40(10) . . ?
O1 S1 O2 119.25(7) . . ?
O1 S1 N1 108.04(7) . . ?
O2 S1 N1 107.37(7) . . ?
O1 S1 C17 106.68(8) . . ?
O2 S1 C17 108.39(8) . . ?
N1 S1 C17 106.47(7) . . ?

_refine_diff_density_max         0.576
_refine_diff_density_min         -0.710
_refine_diff_density_rms         0.271

_shelxl_version_number           2014/6

####################################################################### 
# 
# 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_160104_0m_a
_database_code_depnum_ccdc_archive 'CCDC 1469310'
_audit_update_record             
;
2016-03-18 deposited with the CCDC.
2016-08-22 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C18 H17 N O4 S'
_chemical_formula_weight         343.38

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      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                   6.5556(3)
_cell_length_b                   11.4813(6)
_cell_length_c                   12.6356(7)
_cell_angle_alpha                113.781(3)
_cell_angle_beta                 98.198(3)
_cell_angle_gamma                93.092(3)
_cell_volume                     854.85(8)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    2863
_cell_measurement_theta_min      3.1520
_cell_measurement_theta_max      23.9559

_exptl_crystal_description       Lump
_exptl_crystal_colour            Colorless
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.334
_exptl_crystal_F_000             360
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.09
_exptl_absorpt_coefficient_mu    0.210
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9039
_exptl_absorpt_correction_T_max  0.9485
_exptl_absorpt_process_details   'SADABS V2014/4 (Bruker AXS Inc.)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(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 8.3333
_diffrn_reflns_number            12221
_diffrn_reflns_av_unetI/netI     0.0425
_diffrn_reflns_av_R_equivalents  0.0363
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         1.790
_diffrn_reflns_theta_max         26.414
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             3495
_reflns_number_gt                2607
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'APEX2 (Bruker AXS, 2010)'
_computing_cell_refinement       'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_data_reduction        'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  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)+(0.0916P)²] 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     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3495
_refine_ls_number_parameters     219
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0685
_refine_ls_R_factor_gt           0.0454
_refine_ls_wR_factor_ref         0.1637
_refine_ls_wR_factor_gt          0.1305
_refine_ls_goodness_of_fit_ref   1.126
_refine_ls_restrained_S_all      1.126
_refine_ls_shift/su_max          0.081
_refine_ls_shift/su_mean         0.002

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_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
C1 C 0.2519(3) 0.9682(2) 0.4726(2) 0.0364(5) Uani 1 1 d . . . . .
C2 C 0.2624(3) 0.8288(2) 0.43531(19) 0.0349(5) Uani 1 1 d . . . . .
C3 C 0.3131(3) 0.7819(2) 0.3283(2) 0.0346(5) Uani 1 1 d . . . . .
C4 C 0.3420(3) 0.8888(2) 0.28972(19) 0.0340(5) Uani 1 1 d . . . . .
H4 H 0.4877 0.9017 0.2828 0.041 Uiso 1 1 calc R U . . .
C5 C 0.2850(5) 1.0774(3) 0.1391(3) 0.0662(8) Uani 1 1 d . . . . .
H5A H 0.3424 1.1098 0.0891 0.099 Uiso 1 1 calc R U . . .
H5B H 0.3606 1.1212 0.2181 0.099 Uiso 1 1 calc R U . . .
H5C H 0.1418 1.0912 0.1377 0.099 Uiso 1 1 calc R U . . .
C6 C -0.0139(3) 0.8489(3) 0.1734(2) 0.0630(8) Uani 1 1 d . . . . .
H6A H -0.0451 0.8139 0.2275 0.095 Uiso 1 1 calc R U . . .
H6B H -0.0793 0.7916 0.0950 0.095 Uiso 1 1 calc R U . . .
H6C H -0.0651 0.9306 0.1937 0.095 Uiso 1 1 calc R U . . .
C7 C 0.2376(3) 0.7637(2) 0.5131(2) 0.0401(5) Uani 1 1 d . . . . .
C8 C 0.3898(4) 0.6938(3) 0.5358(2) 0.0512(7) Uani 1 1 d . . . . .
H8 H 0.5080 0.6886 0.5020 0.061 Uiso 1 1 calc R U . . .
C9 C 0.3687(5) 0.6320(3) 0.6076(3) 0.0650(8) Uani 1 1 d . . . . .
H9 H 0.4733 0.5864 0.6230 0.078 Uiso 1 1 calc R U . . .
C10 C 0.1959(5) 0.6373(3) 0.6559(3) 0.0749(9) Uani 1 1 d . . . . .
H10 H 0.1823 0.5955 0.7045 0.090 Uiso 1 1 calc R U . . .
C11 C 0.0418(6) 0.7037(4) 0.6335(3) 0.0887(12) Uani 1 1 d . . . . .
H11 H -0.0777 0.7056 0.6657 0.106 Uiso 1 1 calc R U . . .
C12 C 0.0625(5) 0.7683(3) 0.5631(3) 0.0693(9) Uani 1 1 d . . . . .
H12 H -0.0418 0.8150 0.5495 0.083 Uiso 1 1 calc R U . . .
C13 C 0.3435(3) 0.6500(2) 0.25305(19) 0.0376(5) Uani 1 1 d . . . . .
C14 C 0.1927(4) 0.5489(2) 0.2296(2) 0.0547(7) Uani 1 1 d . . . . .
H14 H 0.0735 0.5643 0.2626 0.066 Uiso 1 1 calc R U . . .
C15 C 0.2203(5) 0.4253(3) 0.1571(3) 0.0711(9) Uani 1 1 d . . . . .
H15 H 0.1179 0.3580 0.1403 0.085 Uiso 1 1 calc R U . . .
C16 C 0.3946(5) 0.4013(3) 0.1104(3) 0.0658(8) Uani 1 1 d . . . . .
H16 H 0.4118 0.3178 0.0620 0.079 Uiso 1 1 calc R U . . .
C17 C 0.5473(5) 0.5007(3) 0.1344(3) 0.0656(8) Uani 1 1 d . . . . .
H17 H 0.6685 0.4841 0.1035 0.079 Uiso 1 1 calc R U . . .
C18 C 0.5193(4) 0.6243(3) 0.2041(2) 0.0532(7) Uani 1 1 d . . . . .
H18 H 0.6206 0.6913 0.2183 0.064 Uiso 1 1 calc R U . . .
N1 N 0.2123(2) 0.86541(18) 0.17981(16) 0.0385(5) Uani 1 1 d . . . . .
O1 O 0.1688(3) 0.8500(2) -0.02175(15) 0.0653(6) Uani 1 1 d . . . . .
O2 O 0.5178(2) 0.89701(19) 0.09795(16) 0.0557(5) Uani 1 1 d . . . . .
O3 O 0.2956(2) 1.00113(14) 0.38491(13) 0.0380(4) Uani 1 1 d . . . . .
O4 O 0.2202(2) 1.04775(15) 0.56377(14) 0.0422(4) Uani 1 1 d . . . . .
S1 S 0.30377(8) 0.91417(6) 0.08924(5) 0.0405(2) 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
C1 O4 1.202(3) . ?
C1 O3 1.367(3) . ?
C1 C2 1.484(3) . ?
C2 C3 1.337(3) . ?
C2 C7 1.476(3) . ?
C3 C13 1.471(3) . ?
C3 C4 1.505(3) . ?
C4 N1 1.436(3) . ?
C4 O3 1.448(3) . ?
C4 H4 0.9800 . ?
C5 S1 1.737(3) . ?
C5 H5A 0.9600 . ?
C5 H5B 0.9600 . ?
C5 H5C 0.9600 . ?
C6 N1 1.472(3) . ?
C6 H6A 0.9600 . ?
C6 H6B 0.9600 . ?
C6 H6C 0.9600 . ?
C7 C12 1.381(3) . ?
C7 C8 1.382(3) . ?
C8 C9 1.375(3) . ?
C8 H8 0.9300 . ?
C9 C10 1.354(4) . ?
C9 H9 0.9300 . ?
C10 C11 1.362(5) . ?
C10 H10 0.9300 . ?
C11 C12 1.384(4) . ?
C11 H11 0.9300 . ?
C12 H12 0.9300 . ?
C13 C18 1.375(3) . ?
C13 C14 1.388(3) . ?
C14 C15 1.383(4) . ?
C14 H14 0.9300 . ?
C15 C16 1.351(4) . ?
C15 H15 0.9300 . ?
C16 C17 1.381(4) . ?
C16 H16 0.9300 . ?
C17 C18 1.374(4) . ?
C17 H17 0.9300 . ?
C18 H18 0.9300 . ?
N1 S1 1.6305(18) . ?
O1 S1 1.4267(18) . ?
O2 S1 1.4225(17) . ?

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
O4 C1 O3 121.1(2) . . ?
O4 C1 C2 130.1(2) . . ?
O3 C1 C2 108.80(19) . . ?
C3 C2 C7 129.1(2) . . ?
C3 C2 C1 108.00(19) . . ?
C7 C2 C1 122.73(19) . . ?
C2 C3 C13 129.5(2) . . ?
C2 C3 C4 109.37(19) . . ?
C13 C3 C4 121.08(19) . . ?
N1 C4 O3 111.61(17) . . ?
N1 C4 C3 113.43(17) . . ?
O3 C4 C3 104.63(17) . . ?
N1 C4 H4 109.0 . . ?
O3 C4 H4 109.0 . . ?
C3 C4 H4 109.0 . . ?
S1 C5 H5A 109.5 . . ?
S1 C5 H5B 109.5 . . ?
H5A C5 H5B 109.5 . . ?
S1 C5 H5C 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
N1 C6 H6A 109.5 . . ?
N1 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
N1 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
C12 C7 C8 118.3(2) . . ?
C12 C7 C2 121.6(2) . . ?
C8 C7 C2 120.09(19) . . ?
C9 C8 C7 120.9(2) . . ?
C9 C8 H8 119.6 . . ?
C7 C8 H8 119.6 . . ?
C10 C9 C8 120.1(3) . . ?
C10 C9 H9 119.9 . . ?
C8 C9 H9 119.9 . . ?
C9 C10 C11 120.3(3) . . ?
C9 C10 H10 119.9 . . ?
C11 C10 H10 119.9 . . ?
C10 C11 C12 120.2(3) . . ?
C10 C11 H11 119.9 . . ?
C12 C11 H11 119.9 . . ?
C7 C12 C11 120.1(3) . . ?
C7 C12 H12 119.9 . . ?
C11 C12 H12 119.9 . . ?
C18 C13 C14 118.8(2) . . ?
C18 C13 C3 121.1(2) . . ?
C14 C13 C3 120.0(2) . . ?
C15 C14 C13 119.8(3) . . ?
C15 C14 H14 120.1 . . ?
C13 C14 H14 120.1 . . ?
C16 C15 C14 120.7(3) . . ?
C16 C15 H15 119.7 . . ?
C14 C15 H15 119.7 . . ?
C15 C16 C17 120.1(3) . . ?
C15 C16 H16 120.0 . . ?
C17 C16 H16 120.0 . . ?
C18 C17 C16 119.7(3) . . ?
C18 C17 H17 120.1 . . ?
C16 C17 H17 120.1 . . ?
C17 C18 C13 120.8(2) . . ?
C17 C18 H18 119.6 . . ?
C13 C18 H18 119.6 . . ?
C4 N1 C6 117.48(17) . . ?
C4 N1 S1 118.96(13) . . ?
C6 N1 S1 118.81(16) . . ?
C1 O3 C4 109.16(16) . . ?
O2 S1 O1 119.15(12) . . ?
O2 S1 N1 106.86(10) . . ?
O1 S1 N1 106.59(10) . . ?
O2 S1 C5 108.22(14) . . ?
O1 S1 C5 108.10(14) . . ?
N1 S1 C5 107.37(12) . . ?

_refine_diff_density_max         0.301
_refine_diff_density_min         -0.335
_refine_diff_density_rms         0.111

_shelxl_version_number           2014/6

