# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2018

####################################################################### 
# 
# 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_002
_database_code_depnum_ccdc_archive 'CCDC 1570920'
_audit_update_record             
;
2017-08-26 deposited with the CCDC.
2018-03-12 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         '	C20 H18 N2 O'
_chemical_formula_sum            '	C20 H18 N2 O'
_chemical_formula_weight         302.36

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'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   'P2(1)/c  '

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

_cell_length_a                   11.586(3)
_cell_length_b                   15.822(3)
_cell_length_c                   8.7845(18)
_cell_angle_alpha                90.00
_cell_angle_beta                 97.997(8)
_cell_angle_gamma                90.00
_cell_volume                     1594.6(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    296
_cell_measurement_reflns_used    3022
_cell_measurement_theta_min      2.19
_cell_measurement_theta_max      26.97

_exptl_crystal_description       BLOCK
_exptl_crystal_colour            COLORLESS
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.33
_exptl_crystal_size_min          0.3
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.259
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             640
_exptl_absorpt_coefficient_mu    0.078
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            16142
_diffrn_reflns_av_R_equivalents  0.0821
_diffrn_reflns_av_sigmaI/netI    0.0967
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         2.19
_diffrn_reflns_theta_max         27.45
_reflns_number_total             3632
_reflns_number_gt                1745
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'Bruker SHELXTL'
_computing_structure_refinement  'Bruker SHELXTL'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0532P)²+0.1551P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3644
_refine_ls_number_parameters     209
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1739
_refine_ls_R_factor_gt           0.0683
_refine_ls_wR_factor_ref         0.1401
_refine_ls_wR_factor_gt          0.1135
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_restrained_S_all      1.048
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.72578(15) 1.03570(10) -0.1019(2) 0.0441(5) Uani 1 1 d . . .
N2 N 0.77564(15) 1.02172(10) 0.0467(2) 0.0478(5) Uani 1 1 d . . .
O1 O 0.50893(14) 0.82718(11) 0.0784(2) 0.0744(5) Uani 1 1 d . . .
C4 C 0.63702(18) 0.98203(12) -0.1468(3) 0.0420(5) Uani 1 1 d . . .
C5 C 0.8135(2) 0.98817(14) 0.3586(3) 0.0549(6) Uani 1 1 d . . .
H5 H 0.8298 1.0420 0.3249 0.066 Uiso 1 1 calc R . .
C6 C 0.71457(19) 0.95893(12) 0.0977(3) 0.0440(6) Uani 1 1 d . . .
C7 C 0.62582(18) 0.93136(12) -0.0208(2) 0.0424(5) Uani 1 1 d . . .
C8 C 0.7785(2) 1.09674(12) -0.1905(2) 0.0429(6) Uani 1 1 d . . .
C9 C 0.7103(2) 1.14602(13) -0.2962(3) 0.0532(6) Uani 1 1 d . . .
H9 H 0.6295 1.1426 -0.3059 0.064 Uiso 1 1 calc R . .
C10 C 0.7672(2) 0.83110(15) 0.4635(3) 0.0603(7) Uani 1 1 d . . .
H10 H 0.7510 0.7773 0.4977 0.072 Uiso 1 1 calc R . .
C11 C 0.74862(18) 0.93300(13) 0.2583(3) 0.0455(6) Uani 1 1 d . . .
C12 C 0.8985(2) 1.10416(13) -0.1702(3) 0.0521(6) Uani 1 1 d . . .
H12 H 0.9439 1.0720 -0.0960 0.063 Uiso 1 1 calc R . .
C13 C 0.8824(3) 1.20695(15) -0.3705(3) 0.0684(7) Uani 1 1 d . . .
H13 H 0.9177 1.2434 -0.4332 0.082 Uiso 1 1 calc R . .
C14 C 0.8325(2) 0.88554(15) 0.5630(3) 0.0548(6) Uani 1 1 d . . .
C15 C 0.7249(2) 0.85386(13) 0.3145(3) 0.0540(6) Uani 1 1 d . . .
H15 H 0.6800 0.8157 0.2511 0.065 Uiso 1 1 calc R . .
C16 C 0.5684(2) 0.97496(13) -0.3011(3) 0.0534(6) Uani 1 1 d . . .
H16A H 0.6170 0.9879 -0.3794 0.064 Uiso 1 1 calc R . .
H16B H 0.5039 1.0146 -0.3110 0.064 Uiso 1 1 calc R . .
C17 C 0.8543(2) 0.96483(15) 0.5072(3) 0.0577(6) Uani 1 1 d . . .
H17 H 0.8977 1.0033 0.5718 0.069 Uiso 1 1 calc R . .
C18 C 0.4625(2) 0.85721(14) -0.1875(3) 0.0601(7) Uani 1 1 d . . .
H18A H 0.3907 0.8890 -0.1903 0.072 Uiso 1 1 calc R . .
H18B H 0.4418 0.7980 -0.2012 0.072 Uiso 1 1 calc R . .
C19 C 0.53269(19) 0.86807(13) -0.0312(3) 0.0494(6) Uani 1 1 d . . .
C20 C 0.7630(2) 1.20067(14) -0.3879(3) 0.0628(7) Uani 1 1 d . . .
H20 H 0.7177 1.2333 -0.4615 0.075 Uiso 1 1 calc R . .
C21 C 0.8795(3) 0.86141(16) 0.7252(3) 0.0771(8) Uani 1 1 d . . .
H21A H 0.8572 0.9033 0.7946 0.116 Uiso 1 1 calc R . .
H21B H 0.9630 0.8580 0.7358 0.116 Uiso 1 1 calc R . .
H21C H 0.8483 0.8075 0.7488 0.116 Uiso 1 1 calc R . .
C22 C 0.9499(2) 1.15958(14) -0.2609(3) 0.0632(7) Uani 1 1 d . . .
H22 H 1.0306 1.1651 -0.2481 0.076 Uiso 1 1 calc R . .
C23 C 0.5225(2) 0.88486(14) -0.3213(3) 0.0631(7) Uani 1 1 d . . .
H23A H 0.4680 0.8812 -0.4154 0.076 Uiso 1 1 calc R . .
H23B H 0.5869 0.8469 -0.3308 0.076 Uiso 1 1 calc R . .


_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
N1 C4 1.349(3) . ?
N1 N2 1.371(2) . ?
N1 C8 1.429(3) . ?
N2 C6 1.333(2) . ?
O1 C19 1.222(3) . ?
C4 C7 1.387(3) . ?
C4 C16 1.478(3) . ?
C5 C17 1.376(3) . ?
C5 C11 1.385(3) . ?
C6 C7 1.426(3) . ?
C6 C11 1.470(3) . ?
C7 C19 1.466(3) . ?
C8 C9 1.375(3) . ?
C8 C12 1.382(3) . ?
C9 C20 1.380(3) . ?
C10 C14 1.376(3) . ?
C10 C15 1.380(3) . ?
C11 C15 1.387(3) . ?
C12 C22 1.375(3) . ?
C13 C20 1.374(3) . ?
C13 C22 1.376(3) . ?
C14 C17 1.383(3) . ?
C14 C21 1.502(3) . ?
C16 C23 1.523(3) . ?
C18 C19 1.506(3) . ?
C18 C23 1.511(3) . ?

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
C4 N1 N2 112.30(16) . . ?
C4 N1 C8 129.22(19) . . ?
N2 N1 C8 118.19(17) . . ?
C6 N2 N1 105.52(17) . . ?
N1 C4 C7 106.45(19) . . ?
N1 C4 C16 127.32(19) . . ?
C7 C4 C16 126.16(19) . . ?
C17 C5 C11 121.3(2) . . ?
N2 C6 C7 110.18(18) . . ?
N2 C6 C11 116.53(19) . . ?
C7 C6 C11 133.29(19) . . ?
C4 C7 C6 105.53(18) . . ?
C4 C7 C19 119.7(2) . . ?
C6 C7 C19 134.7(2) . . ?
C9 C8 C12 120.8(2) . . ?
C9 C8 N1 120.1(2) . . ?
C12 C8 N1 119.04(19) . . ?
C8 C9 C20 119.4(2) . . ?
C14 C10 C15 122.0(2) . . ?
C5 C11 C15 117.3(2) . . ?
C5 C11 C6 118.95(19) . . ?
C15 C11 C6 123.6(2) . . ?
C22 C12 C8 119.2(2) . . ?
C20 C13 C22 120.3(2) . . ?
C10 C14 C17 117.0(2) . . ?
C10 C14 C21 122.5(2) . . ?
C17 C14 C21 120.4(2) . . ?
C10 C15 C11 120.7(2) . . ?
C4 C16 C23 108.19(19) . . ?
C5 C17 C14 121.6(2) . . ?
C19 C18 C23 115.3(2) . . ?
O1 C19 C7 123.9(2) . . ?
O1 C19 C18 120.4(2) . . ?
C7 C19 C18 115.7(2) . . ?
C13 C20 C9 120.0(2) . . ?
C12 C22 C13 120.2(2) . . ?
C18 C23 C16 111.8(2) . . ?

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        27.45
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.148
_refine_diff_density_min         -0.231
_refine_diff_density_rms         0.045
####################################################################### 
# 
# 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_001
_database_code_depnum_ccdc_archive 'CCDC 1583744'
_audit_update_record             
;
2017-11-03 deposited with the CCDC.
2018-03-12 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C15 H15 N O3'
_chemical_formula_sum            '	C15 H15 N O3'
_chemical_formula_weight         257.28

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'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   'P2(1)/c  '

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

_cell_length_a                   12.836(7)
_cell_length_b                   8.234(3)
_cell_length_c                   13.790(10)
_cell_angle_alpha                90.00
_cell_angle_beta                 117.679(17)
_cell_angle_gamma                90.00
_cell_volume                     1290.7(12)
_cell_formula_units_Z            4
_cell_measurement_temperature    296
_cell_measurement_reflns_used    2269
_cell_measurement_theta_min      2.96
_cell_measurement_theta_max      25.97

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.33
_exptl_crystal_size_min          0.3
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.324
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             544
_exptl_absorpt_coefficient_mu    0.093
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            5381
_diffrn_reflns_av_R_equivalents  0.0285
_diffrn_reflns_av_sigmaI/netI    0.0401
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         1.79
_diffrn_reflns_theta_max         25.00
_reflns_number_total             2271
_reflns_number_gt                1517
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'Bruker SHELXTL'
_computing_structure_refinement  'Bruker SHELXTL'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0929P)²+0.7744P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2154
_refine_ls_number_parameters     174
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0896
_refine_ls_R_factor_gt           0.0595
_refine_ls_wR_factor_ref         0.1884
_refine_ls_wR_factor_gt          0.1671
_refine_ls_goodness_of_fit_ref   1.082
_refine_ls_restrained_S_all      1.084
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.3407(2) -0.0397(3) 0.14320(17) 0.0548(6) Uani 1 1 d . . .
O2 O 0.3528(2) -0.0850(3) 0.48158(16) 0.0578(7) Uani 1 1 d . . .
O3 O 0.2796(2) 0.3173(3) 0.47251(19) 0.0673(7) Uani 1 1 d . . .
H3 H 0.2792 0.3807 0.5181 0.101 Uiso 1 1 calc R . .
C4 C 0.3648(3) -0.1620(4) 0.3992(2) 0.0428(7) Uani 1 1 d . . .
C5 C 0.3574(2) -0.1250(4) 0.2222(2) 0.0400(7) Uani 1 1 d . . .
C6 C 0.3369(2) -0.0677(4) 0.3111(2) 0.0383(7) Uani 1 1 d . . .
N1 N 0.3149(3) 0.1657(4) 0.5195(2) 0.0600(8) Uani 1 1 d U . .
C8 C 0.1593(3) 0.1129(3) 0.2483(2) 0.0401(7) Uani 1 1 d . . .
C9 C 0.1231(3) 0.1947(4) 0.1500(2) 0.0472(8) Uani 1 1 d . . .
H9 H 0.1787 0.2461 0.1354 0.057 Uiso 1 1 calc R . .
C10 C 0.3175(3) 0.0710(4) 0.4460(2) 0.0502(8) Uani 1 1 d U . .
C11 C 0.4049(3) -0.3319(4) 0.4160(3) 0.0529(8) Uani 1 1 d . . .
H11A H 0.3663 -0.3922 0.4506 0.063 Uiso 1 1 calc R . .
H11B H 0.4892 -0.3365 0.4631 0.063 Uiso 1 1 calc R . .
C12 C 0.3748(3) -0.4055(4) 0.3051(3) 0.0591(9) Uani 1 1 d . . .
H12A H 0.2910 -0.4276 0.2662 0.071 Uiso 1 1 calc R . .
H12B H 0.4160 -0.5079 0.3156 0.071 Uiso 1 1 calc R . .
C13 C 0.0754(3) 0.0392(4) 0.2697(3) 0.0528(9) Uani 1 1 d . . .
H13 H 0.0984 -0.0164 0.3352 0.063 Uiso 1 1 calc R . .
C14 C 0.0039(3) 0.2014(4) 0.0723(2) 0.0532(9) Uani 1 1 d . . .
C15 C 0.2905(3) 0.0931(4) 0.3271(2) 0.0421(7) Uani 1 1 d . . .
H15 H 0.3359 0.1835 0.3196 0.051 Uiso 1 1 calc R . .
C16 C -0.0424(3) 0.0473(5) 0.1945(3) 0.0667(10) Uani 1 1 d . . .
H16 H -0.0984 -0.0016 0.2098 0.080 Uiso 1 1 calc R . .
C17 C 0.4083(3) -0.2929(4) 0.2361(3) 0.0563(9) Uani 1 1 d . . .
H17A H 0.4933 -0.2846 0.2701 0.068 Uiso 1 1 calc R . .
H17B H 0.3819 -0.3412 0.1643 0.068 Uiso 1 1 calc R . .
C18 C -0.0766(3) 0.1272(5) 0.0975(3) 0.0618(10) Uani 1 1 d . . .
H18 H -0.1561 0.1315 0.0475 0.074 Uiso 1 1 calc R . .
C19 C -0.0347(4) 0.2813(6) -0.0381(3) 0.0840(13) Uani 1 1 d . . .
H19A H -0.0662 0.2005 -0.0947 0.126 Uiso 1 1 calc R . .
H19B H 0.0316 0.3330 -0.0395 0.126 Uiso 1 1 calc R . .
H19C H -0.0941 0.3610 -0.0501 0.126 Uiso 1 1 calc R . .


_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 C5 1.228(3) . ?
O2 C4 1.371(4) . ?
O2 C10 1.374(4) . ?
O3 N1 1.383(4) . ?
C4 C6 1.343(4) . ?
C4 C11 1.471(5) . ?
C5 C6 1.447(4) . ?
C5 C17 1.503(4) . ?
C6 C15 1.510(4) . ?
N1 C10 1.292(4) . ?
C8 C13 1.382(4) . ?
C8 C9 1.386(4) . ?
C8 C15 1.531(4) . ?
C9 C14 1.403(4) . ?
C10 C15 1.521(4) . ?
C11 C12 1.519(5) . ?
C12 C17 1.526(5) . ?
C13 C16 1.382(5) . ?
C14 C18 1.377(5) . ?
C14 C19 1.515(5) . ?
C16 C18 1.366(5) . ?

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
C4 O2 C10 106.3(2) . . ?
C6 C4 O2 113.4(3) . . ?
C6 C4 C11 128.2(3) . . ?
O2 C4 C11 118.4(2) . . ?
O1 C5 C6 122.6(3) . . ?
O1 C5 C17 121.7(3) . . ?
C6 C5 C17 115.5(2) . . ?
C4 C6 C5 120.1(3) . . ?
C4 C6 C15 109.4(2) . . ?
C5 C6 C15 130.5(3) . . ?
C10 N1 O3 107.4(3) . . ?
C13 C8 C9 118.8(3) . . ?
C13 C8 C15 120.7(3) . . ?
C9 C8 C15 120.3(3) . . ?
C8 C9 C14 121.2(3) . . ?
N1 C10 O2 114.1(3) . . ?
N1 C10 C15 134.2(3) . . ?
O2 C10 C15 111.7(3) . . ?
C4 C11 C12 108.3(3) . . ?
C11 C12 C17 111.8(3) . . ?
C8 C13 C16 120.5(3) . . ?
C18 C14 C9 118.0(3) . . ?
C18 C14 C19 120.9(3) . . ?
C9 C14 C19 121.1(3) . . ?
C6 C15 C10 98.3(2) . . ?
C6 C15 C8 111.6(2) . . ?
C10 C15 C8 113.8(2) . . ?
C18 C16 C13 120.0(3) . . ?
C5 C17 C12 114.0(3) . . ?
C16 C18 C14 121.5(3) . . ?

_diffrn_measured_fraction_theta_max 0.948
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.948
_refine_diff_density_max         0.597
_refine_diff_density_min         -0.255
_refine_diff_density_rms         0.052
####################################################################### 
# 
# 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_003
_database_code_depnum_ccdc_archive 'CCDC 1576085'
_audit_update_record             
;
2017-09-22 deposited with the CCDC.
2018-03-12 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         '	C17 H14 N2 O S'
_chemical_formula_sum            '	C17 H14 N2 O S'
_chemical_formula_weight         294.36

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

_symmetry_cell_setting           Orthorhombic
_symmetry_space_group_name_H-M   'Pbca '

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

_cell_length_a                   31.267(8)
_cell_length_b                   8.132(3)
_cell_length_c                   22.702(6)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     5773(3)
_cell_formula_units_Z            16
_cell_measurement_temperature    296
_cell_measurement_reflns_used    4310
_cell_measurement_theta_min      2.22
_cell_measurement_theta_max      21.73

_exptl_crystal_description       BLOCK
_exptl_crystal_colour            COLORLESS
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.33
_exptl_crystal_size_min          0.3
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.355
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             2464
_exptl_absorpt_coefficient_mu    0.224
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            27936
_diffrn_reflns_av_R_equivalents  0.1114
_diffrn_reflns_av_sigmaI/netI    0.1270
_diffrn_reflns_limit_h_min       -33
_diffrn_reflns_limit_h_max       40
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         1.30
_diffrn_reflns_theta_max         27.42
_reflns_number_total             6584
_reflns_number_gt                3000
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'Bruker SHELXTL'
_computing_structure_refinement  'Bruker SHELXTL'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.1143P)²+0.4409P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         6568
_refine_ls_number_parameters     379
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.2036
_refine_ls_R_factor_gt           0.0799
_refine_ls_wR_factor_ref         0.2381
_refine_ls_wR_factor_gt          0.1818
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_restrained_S_all      1.036
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.12016(3) 0.85663(17) 0.03789(5) 0.0600(4) Uani 1 1 d . . .
N1 N 0.03012(9) 0.7791(4) 0.06028(11) 0.0394(8) Uani 1 1 d . . .
O1 O 0.01251(10) 0.8507(4) -0.12947(11) 0.0598(8) Uani 1 1 d . . .
N2 N -0.01049(9) 0.7138(4) 0.06280(11) 0.0388(8) Uani 1 1 d . . .
C2 C 0.07917(11) 0.8764(5) -0.01223(15) 0.0396(9) Uani 1 1 d . . .
C3 C -0.00001(11) 0.7720(5) -0.03061(14) 0.0348(9) Uani 1 1 d . . .
C4 C 0.03688(11) 0.8138(5) 0.00384(15) 0.0375(9) Uani 1 1 d . . .
C5 C -0.02887(11) 0.7067(5) 0.00903(14) 0.0363(9) Uani 1 1 d . . .
C6 C -0.01018(13) 0.7844(5) -0.09303(16) 0.0451(10) Uani 1 1 d . . .
C13 C -0.01569(12) 0.7629(5) 0.16820(15) 0.0461(10) Uani 1 1 d . . .
H13 H 0.0007 0.8576 0.1636 0.055 Uiso 1 1 calc R . .
C7 C 0.13691(15) 1.0001(7) -0.05772(19) 0.0680(14) Uani 1 1 d . . .
H7 H 0.1519 1.0558 -0.0870 0.082 Uiso 1 1 calc R . .
C14 C -0.02698(11) 0.6686(5) 0.11950(15) 0.0385(10) Uani 1 1 d . . .
C15 C -0.05263(13) 0.5320(6) 0.12583(16) 0.0493(11) Uani 1 1 d . . .
H15 H -0.0605 0.4702 0.0931 0.059 Uiso 1 1 calc R . .
C8 C -0.08468(15) 0.6923(8) -0.06585(18) 0.0787(17) Uani 1 1 d . . .
H8A H -0.1052 0.6122 -0.0800 0.094 Uiso 1 1 calc R . .
H8B H -0.0994 0.7971 -0.0635 0.094 Uiso 1 1 calc R . .
C9 C -0.07242(12) 0.6443(6) -0.00536(17) 0.0508(11) Uani 1 1 d . . .
H9A H -0.0729 0.5254 -0.0019 0.061 Uiso 1 1 calc R . .
H9B H -0.0929 0.6889 0.0224 0.061 Uiso 1 1 calc R . .
C10 C 0.09260(12) 0.9564(5) -0.06357(16) 0.0480(11) Uani 1 1 d . . .
H10 H 0.0756 0.9779 -0.0962 0.058 Uiso 1 1 calc R . .
C16 C -0.02899(13) 0.7142(6) 0.22297(16) 0.0559(12) Uani 1 1 d . . .
H16 H -0.0208 0.7751 0.2558 0.067 Uiso 1 1 calc R . .
C17 C -0.05405(14) 0.5778(6) 0.23042(18) 0.0605(13) Uani 1 1 d . . .
H17 H -0.0626 0.5457 0.2679 0.073 Uiso 1 1 calc R . .
C18 C -0.06651(13) 0.4880(6) 0.18131(18) 0.0575(12) Uani 1 1 d . . .
H18 H -0.0844 0.3975 0.1859 0.069 Uiso 1 1 calc R . .
C11 C 0.15485(13) 0.9545(6) -0.00717(19) 0.0628(13) Uani 1 1 d . . .
H11 H 0.1833 0.9743 0.0023 0.075 Uiso 1 1 calc R . .
C12 C -0.05147(13) 0.7075(7) -0.10993(17) 0.0718(15) Uani 1 1 d . . .
H12A H -0.0631 0.7702 -0.1425 0.086 Uiso 1 1 calc R . .
H12B H -0.0453 0.5981 -0.1247 0.086 Uiso 1 1 calc R . .
S2 S 0.12550(4) 0.56825(18) 0.28498(5) 0.0654(4) Uani 1 1 d . . .
N3 N 0.21727(9) 0.5912(4) 0.30660(12) 0.0440(8) Uani 1 1 d . . .
C19 C 0.27992(11) 0.5657(5) 0.36684(15) 0.0403(10) Uani 1 1 d . . .
N4 N 0.26104(9) 0.5870(4) 0.30995(12) 0.0432(8) Uani 1 1 d . . .
C39 C 0.20841(11) 0.6205(5) 0.25046(16) 0.0429(10) Uani 1 1 d . . .
C28 C 0.27926(11) 0.6118(5) 0.25675(16) 0.0413(10) Uani 1 1 d . . .
C29 C 0.16305(11) 0.6278(5) 0.23423(15) 0.0402(10) Uani 1 1 d . . .
O2 O 0.22872(11) 0.6939(6) 0.11781(13) 0.1002(14) Uani 1 1 d . . .
C31 C 0.24672(12) 0.6343(5) 0.21659(15) 0.0436(10) Uani 1 1 d . . .
C20 C 0.31577(12) 0.4693(5) 0.37395(17) 0.0499(11) Uani 1 1 d . . .
H20 H 0.3285 0.4186 0.3417 0.060 Uiso 1 1 calc R . .
C21 C 0.26105(13) 0.6410(6) 0.41492(17) 0.0532(12) Uani 1 1 d . . .
H21 H 0.2372 0.7080 0.4098 0.064 Uiso 1 1 calc R . .
C22 C 0.33245(13) 0.4491(6) 0.42986(19) 0.0594(13) Uani 1 1 d . . .
H22 H 0.3571 0.3865 0.4350 0.071 Uiso 1 1 calc R . .
C36 C 0.09884(14) 0.6664(6) 0.1862(2) 0.0610(13) Uani 1 1 d . . .
H36 H 0.0803 0.6960 0.1560 0.073 Uiso 1 1 calc R . .
C23 C 0.27758(14) 0.6165(7) 0.47037(17) 0.0630(13) Uani 1 1 d . . .
H23 H 0.2647 0.6650 0.5029 0.076 Uiso 1 1 calc R . .
C32 C 0.14434(12) 0.6766(5) 0.18086(18) 0.0486(11) Uani 1 1 d . . .
H32 H 0.1591 0.7101 0.1474 0.058 Uiso 1 1 calc R . .
C24 C 0.31344(14) 0.5194(7) 0.47748(19) 0.0669(14) Uani 1 1 d . . .
H24 H 0.3246 0.5020 0.5149 0.080 Uiso 1 1 calc R . .
C37 C 0.08528(13) 0.6110(6) 0.23794(19) 0.0584(12) Uani 1 1 d . . .
H37 H 0.0565 0.5973 0.2473 0.070 Uiso 1 1 calc R . .
C33 C 0.25574(15) 0.6631(7) 0.15471(18) 0.0655(14) Uani 1 1 d . . .
C34 C 0.33274(15) 0.6896(7) 0.1835(2) 0.0780(16) Uani 1 1 d . . .
H34A H 0.3325 0.8084 0.1872 0.094 Uiso 1 1 calc R . .
H34B H 0.3610 0.6581 0.1699 0.094 Uiso 1 1 calc R . .
C35 C 0.32613(12) 0.6173(6) 0.24351(18) 0.0574(12) Uani 1 1 d . . .
H35A H 0.3380 0.5071 0.2449 0.069 Uiso 1 1 calc R . .
H35B H 0.3407 0.6837 0.2728 0.069 Uiso 1 1 calc R . .
C38 C 0.30164(16) 0.6431(8) 0.1381(2) 0.0930(19) Uani 1 1 d . . .
H38A H 0.3065 0.5290 0.1277 0.112 Uiso 1 1 calc R . .
H38B H 0.3071 0.7087 0.1033 0.112 Uiso 1 1 calc R . .


_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 C11 1.690(5) . ?
S1 C2 1.721(4) . ?
N1 C4 1.329(4) . ?
N1 N2 1.378(4) . ?
O1 C6 1.216(4) . ?
N2 C5 1.350(4) . ?
N2 C14 1.434(4) . ?
C2 C10 1.399(5) . ?
C2 C4 1.463(5) . ?
C3 C5 1.381(5) . ?
C3 C4 1.434(5) . ?
C3 C6 1.456(5) . ?
C5 C9 1.490(5) . ?
C6 C12 1.485(6) . ?
C13 C16 1.370(5) . ?
C13 C14 1.391(5) . ?
C7 C11 1.330(6) . ?
C7 C10 1.436(6) . ?
C14 C15 1.378(6) . ?
C15 C18 1.379(5) . ?
C8 C12 1.447(6) . ?
C8 C9 1.478(6) . ?
C16 C17 1.368(6) . ?
C17 C18 1.389(6) . ?
S2 C37 1.686(4) . ?
S2 C29 1.715(4) . ?
N3 C39 1.326(5) . ?
N3 N4 1.371(4) . ?
C19 C20 1.377(5) . ?
C19 C21 1.384(5) . ?
C19 N4 1.431(4) . ?
N4 C28 1.351(4) . ?
C39 C31 1.428(5) . ?
C39 C29 1.466(5) . ?
C28 C31 1.378(5) . ?
C28 C35 1.497(5) . ?
C29 C32 1.403(5) . ?
O2 C33 1.216(5) . ?
C31 C33 1.452(5) . ?
C20 C22 1.382(5) . ?
C21 C23 1.375(5) . ?
C22 C24 1.360(6) . ?
C36 C37 1.327(6) . ?
C36 C32 1.430(6) . ?
C23 C24 1.381(6) . ?
C33 C38 1.492(6) . ?
C34 C38 1.466(6) . ?
C34 C35 1.498(6) . ?

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
C11 S1 C2 91.9(2) . . ?
C4 N1 N2 105.6(3) . . ?
C5 N2 N1 111.8(3) . . ?
C5 N2 C14 130.3(3) . . ?
N1 N2 C14 117.9(3) . . ?
C10 C2 C4 129.8(3) . . ?
C10 C2 S1 111.7(3) . . ?
C4 C2 S1 118.4(3) . . ?
C5 C3 C4 105.1(3) . . ?
C5 C3 C6 121.2(3) . . ?
C4 C3 C6 133.6(3) . . ?
N1 C4 C3 110.3(3) . . ?
N1 C4 C2 117.3(3) . . ?
C3 C4 C2 132.3(3) . . ?
N2 C5 C3 107.1(3) . . ?
N2 C5 C9 127.0(3) . . ?
C3 C5 C9 125.8(3) . . ?
O1 C6 C3 124.5(4) . . ?
O1 C6 C12 121.2(3) . . ?
C3 C6 C12 114.3(3) . . ?
C16 C13 C14 119.0(4) . . ?
C11 C7 C10 114.7(4) . . ?
C15 C14 C13 120.6(3) . . ?
C15 C14 N2 120.6(3) . . ?
C13 C14 N2 118.7(3) . . ?
C14 C15 C18 119.2(4) . . ?
C12 C8 C9 118.6(4) . . ?
C8 C9 C5 110.6(3) . . ?
C2 C10 C7 109.1(3) . . ?
C17 C16 C13 121.4(4) . . ?
C16 C17 C18 119.2(4) . . ?
C15 C18 C17 120.6(4) . . ?
C7 C11 S1 112.5(3) . . ?
C8 C12 C6 118.8(4) . . ?
C37 S2 C29 91.5(2) . . ?
C39 N3 N4 105.4(3) . . ?
C20 C19 C21 120.4(3) . . ?
C20 C19 N4 120.7(3) . . ?
C21 C19 N4 118.9(3) . . ?
C28 N4 N3 111.6(3) . . ?
C28 N4 C19 130.7(3) . . ?
N3 N4 C19 117.7(3) . . ?
N3 C39 C31 110.9(3) . . ?
N3 C39 C29 116.8(3) . . ?
C31 C39 C29 132.3(3) . . ?
N4 C28 C31 107.5(3) . . ?
N4 C28 C35 126.7(3) . . ?
C31 C28 C35 125.9(3) . . ?
C32 C29 C39 129.2(3) . . ?
C32 C29 S2 112.0(3) . . ?
C39 C29 S2 118.8(3) . . ?
C28 C31 C39 104.6(3) . . ?
C28 C31 C33 121.2(3) . . ?
C39 C31 C33 134.2(4) . . ?
C19 C20 C22 118.8(4) . . ?
C23 C21 C19 119.8(4) . . ?
C24 C22 C20 121.0(4) . . ?
C37 C36 C32 114.4(4) . . ?
C21 C23 C24 119.7(4) . . ?
C29 C32 C36 109.0(4) . . ?
C22 C24 C23 120.2(4) . . ?
C36 C37 S2 113.1(3) . . ?
O2 C33 C31 124.4(4) . . ?
O2 C33 C38 121.1(4) . . ?
C31 C33 C38 114.4(4) . . ?
C38 C34 C35 116.5(4) . . ?
C28 C35 C34 109.2(3) . . ?
C34 C38 C33 115.6(4) . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        27.42
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.392
_refine_diff_density_min         -0.496
_refine_diff_density_rms         0.122
