# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2017

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

data_mx4258
_database_code_depnum_ccdc_archive 'CCDC 1497705'
_audit_update_record             
;
2016-08-04 deposited with the CCDC.
2017-01-03 downloaded from the CCDC.
;
_audit_creation_date             2015-11-11
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.09.30 svn.r3233 for OlexSys, GUI svn.r5103)
;
_shelxl_version_number           2013-4
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C13 H12 N2 O'
_chemical_formula_sum            'C13 H12 N2 O'
_chemical_formula_weight         212.25
_chemical_absolute_configuration unk
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 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'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           33
_space_group_name_H-M_alt        'P n a 21'
_space_group_name_Hall           'P 2c -2n'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z+1/2'
'x+1/2, -y+1/2, z'
'-x+1/2, y+1/2, z+1/2'

_cell_length_a                   9.077(4)
_cell_length_b                   10.400(4)
_cell_length_c                   11.750(5)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1109.3(8)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3642
_cell_measurement_temperature    173.1500
_cell_measurement_theta_max      27.4841
_cell_measurement_theta_min      1.7331
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.082
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.73899
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrystalClear (Rigaku Inc., 2007)'
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.271
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             448
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.07
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0361
_diffrn_reflns_av_unetI/netI     0.0287
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            6686
_diffrn_reflns_point_group_measured_fraction_full 0.810
_diffrn_reflns_point_group_measured_fraction_max 0.801
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         27.454
_diffrn_reflns_theta_min         2.979
_diffrn_ambient_temperature      173.1500
_diffrn_detector_area_resol_mean 28.5714
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_details      
;
scan:
	Number of images: 330
	           Slice: -110.0000 - 55.0000
	     Image width: 0.5000
	        Exp time: 7.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	             Chi: 45.0000
	             Phi: 0.0000
	             XTD: 44.9841
	          2theta: -20.2467
scan:
	Number of images: 240
	           Slice: -80.0000 - 40.0000
	     Image width: 0.5000
	        Exp time: 7.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	             Chi: 45.0000
	             Phi: 90.0000
	             XTD: 44.9841
	          2theta: -20.2467
;
_diffrn_measurement_device       
;
Saturn724+ (2x2 bin mode)
;
_diffrn_measurement_device_details 
;
AFC10: Fixed Chi 2 circle
;
_diffrn_measurement_device_type  'Saturn724+ CCD'
_diffrn_measurement_method       'ω scans at fixed χ = 45°'
_diffrn_number_total             1489
_diffrn_orient_matrix_type       d*Trek
_diffrn_orient_matrix_UB_11      -0.1071
_diffrn_orient_matrix_UB_12      -0.0254
_diffrn_orient_matrix_UB_13      -0.0050
_diffrn_orient_matrix_UB_21      0.0110
_diffrn_orient_matrix_UB_22      -0.0282
_diffrn_orient_matrix_UB_23      -0.0913
_diffrn_orient_matrix_UB_31      0.0175
_diffrn_orient_matrix_UB_32      -0.0789
_diffrn_orient_matrix_UB_33      0.0265
_diffrn_radiation_detector       CCD
_diffrn_radiation_monochromator  Confocal
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Rotating Anode'
_diffrn_source_current           24.0000
_diffrn_source_power             1.2000
_diffrn_source_voltage           50.0000
_diffrn_special_details          
;
 ?
;
_reflns_Friedel_coverage         0.535
_reflns_Friedel_fraction_full    0.605
_reflns_Friedel_fraction_max     0.587
_reflns_number_gt                1993
_reflns_number_total             2035
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrystalClear (Rigaku Inc., 2007)'
_computing_data_collection       'CrystalClear (Rigaku Inc., 2007)'
_computing_data_reduction        'CrystalClear (Rigaku Inc., 2007)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'CIFTAB (Sheldrick, 2013)'
_computing_structure_refinement  'SHELXL (Sheldrick, 2014)'
_computing_structure_solution    
;
'SHELXT (Sheldrick, 2014)'
;
_refine_diff_density_max         0.196
_refine_diff_density_min         -0.145
_refine_diff_density_rms         0.036
_refine_ls_abs_structure_details 
;
 Flack x determined using 651 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   0.2(10)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.013
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     145
_refine_ls_number_reflns         2035
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0383
_refine_ls_R_factor_gt           0.0374
_refine_ls_restrained_S_all      1.013
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1000P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1194
_refine_ls_wR_factor_ref         0.1208
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 N1(H1), N2(H2), C2(H2A), C3(H3), C4(H4), C5(H5), C6(H6), C9(H9), C10(H10),
 C11(H11), C12(H12), C13(H13)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.62395(16) 0.77745(16) 0.49900(14) 0.0336(4) Uani 1 1 d . . . . .
N1 N 0.4059(2) 0.79934(17) 0.59305(15) 0.0279(4) Uani 1 1 d . . . . .
H1 H 0.3118 0.7922 0.5875 0.033 Uiso 1 1 calc R . . . .
N2 N 0.4092(2) 0.71707(18) 0.41330(15) 0.0278(4) Uani 1 1 d . . . . .
H2 H 0.3155 0.7108 0.4226 0.033 Uiso 1 1 calc R . . . .
C1 C 0.4639(2) 0.84502(18) 0.69736(18) 0.0270(4) Uani 1 1 d . . . . .
C2 C 0.5839(2) 0.9286(2) 0.7025(2) 0.0310(4) Uani 1 1 d . . . . .
H2A H 0.6289 0.9566 0.6358 0.037 Uiso 1 1 calc R . . . .
C3 C 0.6357(3) 0.96970(18) 0.8070(2) 0.0378(5) Uani 1 1 d . . . . .
H3 H 0.7169 1.0241 0.8102 0.045 Uiso 1 1 calc R . . . .
C4 C 0.5685(3) 0.9310(2) 0.9070(2) 0.0397(5) Uani 1 1 d . . . . .
H4 H 0.6051 0.9579 0.9770 0.048 Uiso 1 1 calc R . . . .
C5 C 0.4463(3) 0.8520(3) 0.9016(2) 0.0428(6) Uani 1 1 d . . . . .
H5 H 0.3985 0.8281 0.9683 0.051 Uiso 1 1 calc R . . . .
C6 C 0.3942(3) 0.8081(2) 0.7976(2) 0.0367(5) Uani 1 1 d . . . . .
H6 H 0.3126 0.7540 0.7949 0.044 Uiso 1 1 calc R . . . .
C7 C 0.4886(2) 0.76584(17) 0.50058(17) 0.0252(4) Uani 1 1 d . . . . .
C8 C 0.4677(2) 0.67556(17) 0.30781(18) 0.0280(4) Uani 1 1 d . . . . .
C9 C 0.4101(3) 0.5652(2) 0.2594(2) 0.0371(5) Uani 1 1 d . . . . .
H9 H 0.3388 0.5181 0.2980 0.045 Uiso 1 1 calc R . . . .
C10 C 0.4589(3) 0.5248(3) 0.1531(2) 0.0484(7) Uani 1 1 d . . . . .
H10 H 0.4184 0.4516 0.1200 0.058 Uiso 1 1 calc R . . . .
C11 C 0.5669(3) 0.5926(3) 0.0966(2) 0.0491(7) Uani 1 1 d . . . . .
H11 H 0.6010 0.5644 0.0263 0.059 Uiso 1 1 calc R . . . .
C12 C 0.6245(3) 0.7030(2) 0.1453(2) 0.0410(5) Uani 1 1 d . . . . .
H12 H 0.6973 0.7490 0.1073 0.049 Uiso 1 1 calc R . . . .
C13 C 0.5744(2) 0.7455(2) 0.25058(19) 0.0315(5) Uani 1 1 d . . . . .
H13 H 0.6122 0.8204 0.2824 0.038 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 C7 1.235(3) . ?
N1 H1 0.8600 . ?
N1 C1 1.416(3) . ?
N1 C7 1.366(3) . ?
N2 H2 0.8600 . ?
N2 C7 1.352(3) . ?
N2 C8 1.416(3) . ?
C1 C2 1.395(3) . ?
C1 C6 1.391(3) . ?
C2 H2A 0.9300 . ?
C2 C3 1.383(3) . ?
C3 H3 0.9300 . ?
C3 C4 1.383(3) . ?
C4 H4 0.9300 . ?
C4 C5 1.382(4) . ?
C5 H5 0.9300 . ?
C5 C6 1.388(3) . ?
C6 H6 0.9300 . ?
C8 C9 1.383(3) . ?
C8 C13 1.385(3) . ?
C9 H9 0.9300 . ?
C9 C10 1.390(4) . ?
C10 H10 0.9300 . ?
C10 C11 1.379(4) . ?
C11 H11 0.9300 . ?
C11 C12 1.385(4) . ?
C12 H12 0.9300 . ?
C12 C13 1.390(3) . ?
C13 H13 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
C1 N1 H1 117.6 . . ?
C7 N1 H1 117.6 . . ?
C7 N1 C1 124.75(17) . . ?
C7 N2 H2 117.3 . . ?
C7 N2 C8 125.33(17) . . ?
C8 N2 H2 117.3 . . ?
C2 C1 N1 122.5(2) . . ?
C6 C1 N1 118.09(18) . . ?
C6 C1 C2 119.4(2) . . ?
C1 C2 H2A 120.1 . . ?
C3 C2 C1 119.8(2) . . ?
C3 C2 H2A 120.1 . . ?
C2 C3 H3 119.5 . . ?
C4 C3 C2 121.0(2) . . ?
C4 C3 H3 119.5 . . ?
C3 C4 H4 120.4 . . ?
C5 C4 C3 119.2(2) . . ?
C5 C4 H4 120.4 . . ?
C4 C5 H5 119.7 . . ?
C4 C5 C6 120.7(2) . . ?
C6 C5 H5 119.7 . . ?
C1 C6 H6 120.0 . . ?
C5 C6 C1 120.0(2) . . ?
C5 C6 H6 120.0 . . ?
O1 C7 N1 122.26(19) . . ?
O1 C7 N2 123.75(19) . . ?
N2 C7 N1 113.98(17) . . ?
C9 C8 N2 118.1(2) . . ?
C9 C8 C13 120.0(2) . . ?
C13 C8 N2 121.82(18) . . ?
C8 C9 H9 120.0 . . ?
C8 C9 C10 120.0(2) . . ?
C10 C9 H9 120.0 . . ?
C9 C10 H10 119.9 . . ?
C11 C10 C9 120.3(2) . . ?
C11 C10 H10 119.9 . . ?
C10 C11 H11 120.2 . . ?
C10 C11 C12 119.6(2) . . ?
C12 C11 H11 120.2 . . ?
C11 C12 H12 119.8 . . ?
C11 C12 C13 120.5(2) . . ?
C13 C12 H12 119.8 . . ?
C8 C13 C12 119.6(2) . . ?
C8 C13 H13 120.2 . . ?
C12 C13 H13 120.2 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H1 O1 0.86 2.12 2.900(3) 149.7 3_465
N2 H2 O1 0.86 1.96 2.779(3) 158.5 3_465

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
N1 C1 C2 C3 -179.89(19) . . . . ?
N1 C1 C6 C5 -179.2(2) . . . . ?
N2 C8 C9 C10 176.6(2) . . . . ?
N2 C8 C13 C12 -177.7(2) . . . . ?
C1 N1 C7 O1 -2.8(3) . . . . ?
C1 N1 C7 N2 175.96(18) . . . . ?
C1 C2 C3 C4 -1.2(3) . . . . ?
C2 C1 C6 C5 -1.5(3) . . . . ?
C2 C3 C4 C5 -1.1(3) . . . . ?
C3 C4 C5 C6 2.2(4) . . . . ?
C4 C5 C6 C1 -0.9(4) . . . . ?
C6 C1 C2 C3 2.5(3) . . . . ?
C7 N1 C1 C2 38.6(3) . . . . ?
C7 N1 C1 C6 -143.8(2) . . . . ?
C7 N2 C8 C9 140.1(2) . . . . ?
C7 N2 C8 C13 -43.1(3) . . . . ?
C8 N2 C7 O1 -1.6(3) . . . . ?
C8 N2 C7 N1 179.72(17) . . . . ?
C8 C9 C10 C11 1.4(4) . . . . ?
C9 C8 C13 C12 -1.0(3) . . . . ?
C9 C10 C11 C12 -1.4(4) . . . . ?
C10 C11 C12 C13 0.1(4) . . . . ?
C11 C12 C13 C8 1.0(3) . . . . ?
C13 C8 C9 C10 -0.2(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_sa4333
_database_code_depnum_ccdc_archive 'CCDC 1423393'
_audit_update_record             
;
2016-07-18 deposited with the CCDC.
2017-01-03 downloaded from the CCDC.
;
_audit_creation_date             2015-09-10
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C23 H19 N O2 S2'
_chemical_formula_sum            'C23 H19 N O2 S2'
_chemical_formula_weight         405.51
_chemical_absolute_configuration ?
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 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'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   8.189(2)
_cell_length_b                   14.782(4)
_cell_length_c                   17.421(5)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2108.7(10)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    6235
_cell_measurement_temperature    173.1500
_cell_measurement_theta_max      27.4770
_cell_measurement_theta_min      1.8068
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.270
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.9006
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrystalClear (Rigaku Inc., 2007)'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.277
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             848
_exptl_crystal_size_max          0.27
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.1
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0464
_diffrn_reflns_av_unetI/netI     0.0457
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            15230
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         27.454
_diffrn_reflns_theta_min         2.714
_diffrn_ambient_temperature      173.1500
_diffrn_detector_area_resol_mean 28.5714
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_details      
;
scan:
	Number of images: 360
	           Slice: -110.0000 - 70.0000
	     Image width: 0.5000
	        Exp time: 12.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	             Chi: 45.0000
	             Phi: 0.0000
	             XTD: 45.1316
	          2theta: -19.7250
scan:
	Number of images: 298
	           Slice: -109.0000 - 40.0000
	     Image width: 0.5000
	        Exp time: 12.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	             Chi: 45.0000
	             Phi: 90.0000
	             XTD: 45.1316
	          2theta: -19.7250
;
_diffrn_measurement_device       
;
Saturn724+ (2x2 bin mode)
;
_diffrn_measurement_device_details 
;
AFC10: Fixed Chi 2 circle
;
_diffrn_measurement_device_type  'Saturn724+ CCD'
_diffrn_measurement_method       'ω scans at fixed χ = 45°'
_diffrn_number_total             2764
_diffrn_orient_matrix_type       d*Trek
_diffrn_orient_matrix_UB_11      0.0435
_diffrn_orient_matrix_UB_12      -0.0088
_diffrn_orient_matrix_UB_13      0.1138
_diffrn_orient_matrix_UB_21      0.0290
_diffrn_orient_matrix_UB_22      -0.0591
_diffrn_orient_matrix_UB_23      -0.0157
_diffrn_orient_matrix_UB_31      0.0476
_diffrn_orient_matrix_UB_32      0.0277
_diffrn_orient_matrix_UB_33      -0.0161
_diffrn_radiation_detector       CCD
_diffrn_radiation_monochromator  'Graphite Monochromator'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Sealed Tube'
_diffrn_source_current           30.0000
_diffrn_source_power             1.5000
_diffrn_source_voltage           50.0000
_diffrn_special_details          
;
 ?
;
_reflns_Friedel_coverage         0.758
_reflns_Friedel_fraction_full    0.993
_reflns_Friedel_fraction_max     0.991
_reflns_number_gt                4450
_reflns_number_total             4800
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrystalClear (Rigaku Inc., 2007)'
_computing_data_collection       'CrystalClear (Rigaku Inc., 2007)'
_computing_data_reduction        'CrystalClear (Rigaku Inc., 2007)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'CIFTAB (Sheldrick, 2013)'
_computing_structure_refinement  'SHELXL (Sheldrick, 2014)'
_computing_structure_solution    
;
'SHELXT (Sheldrick, 2014)'
;
_refine_diff_density_max         0.188
_refine_diff_density_min         -0.209
_refine_diff_density_rms         0.041
_refine_ls_abs_structure_details 
;
 Flack x determined using 1486 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   1.01(4)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.150
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     254
_refine_ls_number_reflns         4800
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0577
_refine_ls_R_factor_gt           0.0520
_refine_ls_restrained_S_all      1.150
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0260P)²+0.7062P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0937
_refine_ls_wR_factor_ref         0.0959
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C6(H6), C9(H9), C10(H10), C11(H11), C12(H12),
 C13(H13), C15(H15), C16(H16), C17(H17), C18(H18), C20(H20), C21(H21)
2.b Idealised Me refined as rotating group:
 C23(H23A,H23B,H23C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 1.05041(10) 0.37406(6) 0.34555(5) 0.03210(19) Uani 1 1 d . . . . .
S2 S 0.74374(11) 0.33660(7) 0.25480(5) 0.0418(2) Uani 1 1 d . . . . .
O1 O 0.8269(4) 0.7253(2) 0.3556(2) 0.0770(10) Uani 1 1 d . . . . .
O2 O 0.6285(3) 0.81269(19) 0.30973(19) 0.0578(8) Uani 1 1 d . . . . .
N1 N 0.9717(4) 0.45703(19) 0.21530(16) 0.0333(7) Uani 1 1 d . . . . .
C1 C 1.1767(4) 0.4720(2) 0.3498(2) 0.0302(7) Uani 1 1 d . . . . .
C2 C 1.1132(5) 0.5536(2) 0.3749(2) 0.0380(8) Uani 1 1 d . . . . .
H2 H 1.0020 0.5589 0.3847 0.046 Uiso 1 1 calc R . . . .
C3 C 1.2145(6) 0.6266(3) 0.3852(2) 0.0505(10) Uani 1 1 d . . . . .
H3 H 1.1713 0.6817 0.4011 0.061 Uiso 1 1 calc R . . . .
C4 C 1.3800(6) 0.6187(3) 0.3721(3) 0.0580(12) Uani 1 1 d . . . . .
H4 H 1.4486 0.6679 0.3801 0.070 Uiso 1 1 calc R . . . .
C5 C 1.4432(5) 0.5377(3) 0.3471(3) 0.0572(11) Uani 1 1 d . . . . .
H5 H 1.5548 0.5325 0.3380 0.069 Uiso 1 1 calc R . . . .
C6 C 1.3426(4) 0.4637(3) 0.3354(2) 0.0413(9) Uani 1 1 d . . . . .
H6 H 1.3856 0.4092 0.3181 0.050 Uiso 1 1 calc R . . . .
C7 C 0.9294(4) 0.3979(2) 0.26353(18) 0.0297(7) Uani 1 1 d . . . . .
C8 C 0.7423(4) 0.2647(2) 0.33733(18) 0.0331(7) Uani 1 1 d . . . . .
C9 C 0.6746(4) 0.2948(2) 0.4055(2) 0.0368(8) Uani 1 1 d . . . . .
H9 H 0.6317 0.3529 0.4090 0.044 Uiso 1 1 calc R . . . .
C10 C 0.6714(5) 0.2378(3) 0.4681(2) 0.0431(9) Uani 1 1 d . . . . .
H10 H 0.6264 0.2576 0.5142 0.052 Uiso 1 1 calc R . . . .
C11 C 0.7341(5) 0.1519(3) 0.4628(2) 0.0482(10) Uani 1 1 d . . . . .
H11 H 0.7340 0.1142 0.5056 0.058 Uiso 1 1 calc R . . . .
C12 C 0.7973(5) 0.1215(3) 0.3942(2) 0.0496(10) Uani 1 1 d . . . . .
H12 H 0.8378 0.0629 0.3905 0.060 Uiso 1 1 calc R . . . .
C13 C 0.8008(4) 0.1776(2) 0.3312(2) 0.0410(9) Uani 1 1 d . . . . .
H13 H 0.8423 0.1568 0.2847 0.049 Uiso 1 1 calc R . . . .
C14 C 0.8678(4) 0.4772(2) 0.1521(2) 0.0357(8) Uani 1 1 d . . . . .
C15 C 0.8641(5) 0.4206(3) 0.0884(2) 0.0431(9) Uani 1 1 d . . . . .
H15 H 0.9254 0.3677 0.0877 0.052 Uiso 1 1 calc R . . . .
C16 C 0.7682(6) 0.4439(3) 0.0260(2) 0.0538(11) Uani 1 1 d . . . . .
H16 H 0.7647 0.4064 -0.0168 0.065 Uiso 1 1 calc R . . . .
C17 C 0.6774(6) 0.5231(3) 0.0272(2) 0.0571(12) Uani 1 1 d . . . . .
H17 H 0.6127 0.5381 -0.0148 0.069 Uiso 1 1 calc R . . . .
C18 C 0.6818(5) 0.5791(3) 0.0894(2) 0.0482(10) Uani 1 1 d . . . . .
H18 H 0.6202 0.6319 0.0893 0.058 Uiso 1 1 calc R . . . .
C19 C 0.7779(4) 0.5579(2) 0.1534(2) 0.0372(8) Uani 1 1 d . . . . .
C20 C 0.7881(4) 0.6170(3) 0.2204(2) 0.0414(9) Uani 1 1 d . . . . .
H20 H 0.8664 0.6014 0.2568 0.050 Uiso 1 1 calc R . . . .
C21 C 0.7014(5) 0.6891(3) 0.2359(2) 0.0458(10) Uani 1 1 d . . . . .
H21 H 0.6203 0.7073 0.2019 0.055 Uiso 1 1 calc R . . . .
C22 C 0.7299(5) 0.7419(3) 0.3063(3) 0.0504(10) Uani 1 1 d . . . . .
C23 C 0.6415(6) 0.8706(3) 0.3755(3) 0.0772(16) Uani 1 1 d . . . . .
H23A H 0.7504 0.8944 0.3786 0.116 Uiso 1 1 calc GR . . . .
H23B H 0.6178 0.8366 0.4211 0.116 Uiso 1 1 calc GR . . . .
H23C H 0.5652 0.9196 0.3708 0.116 Uiso 1 1 calc GR . . . .


_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 1.781(3) . ?
S1 C7 1.774(3) . ?
S2 C7 1.776(3) . ?
S2 C8 1.788(3) . ?
O1 C22 1.195(5) . ?
O2 C22 1.338(5) . ?
O2 C23 1.434(5) . ?
N1 C7 1.261(4) . ?
N1 C14 1.423(4) . ?
C1 C2 1.383(5) . ?
C1 C6 1.387(5) . ?
C2 H2 0.9300 . ?
C2 C3 1.374(5) . ?
C3 H3 0.9300 . ?
C3 C4 1.379(6) . ?
C4 H4 0.9300 . ?
C4 C5 1.375(6) . ?
C5 H5 0.9300 . ?
C5 C6 1.384(5) . ?
C6 H6 0.9300 . ?
C8 C9 1.384(5) . ?
C8 C13 1.378(5) . ?
C9 H9 0.9300 . ?
C9 C10 1.378(5) . ?
C10 H10 0.9300 . ?
C10 C11 1.372(5) . ?
C11 H11 0.9300 . ?
C11 C12 1.378(5) . ?
C12 H12 0.9300 . ?
C12 C13 1.376(5) . ?
C13 H13 0.9300 . ?
C14 C15 1.390(5) . ?
C14 C19 1.401(5) . ?
C15 H15 0.9300 . ?
C15 C16 1.384(5) . ?
C16 H16 0.9300 . ?
C16 C17 1.387(6) . ?
C17 H17 0.9300 . ?
C17 C18 1.363(6) . ?
C18 H18 0.9300 . ?
C18 C19 1.401(5) . ?
C19 C20 1.461(5) . ?
C20 H20 0.9300 . ?
C20 C21 1.308(5) . ?
C21 H21 0.9300 . ?
C21 C22 1.472(6) . ?
C23 H23A 0.9600 . ?
C23 H23B 0.9600 . ?
C23 H23C 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
C7 S1 C1 101.34(15) . . ?
C7 S2 C8 103.91(15) . . ?
C22 O2 C23 117.1(4) . . ?
C7 N1 C14 119.8(3) . . ?
C2 C1 S1 120.2(3) . . ?
C2 C1 C6 120.2(4) . . ?
C6 C1 S1 119.3(3) . . ?
C1 C2 H2 120.0 . . ?
C3 C2 C1 119.9(4) . . ?
C3 C2 H2 120.0 . . ?
C2 C3 H3 119.8 . . ?
C2 C3 C4 120.3(4) . . ?
C4 C3 H3 119.8 . . ?
C3 C4 H4 120.1 . . ?
C5 C4 C3 119.8(4) . . ?
C5 C4 H4 120.1 . . ?
C4 C5 H5 119.7 . . ?
C4 C5 C6 120.7(4) . . ?
C6 C5 H5 119.7 . . ?
C1 C6 H6 120.4 . . ?
C5 C6 C1 119.1(4) . . ?
C5 C6 H6 120.4 . . ?
S1 C7 S2 116.46(18) . . ?
N1 C7 S1 121.4(3) . . ?
N1 C7 S2 122.1(3) . . ?
C9 C8 S2 120.1(3) . . ?
C13 C8 S2 119.4(3) . . ?
C13 C8 C9 120.4(3) . . ?
C8 C9 H9 120.3 . . ?
C10 C9 C8 119.4(3) . . ?
C10 C9 H9 120.3 . . ?
C9 C10 H10 119.9 . . ?
C11 C10 C9 120.3(4) . . ?
C11 C10 H10 119.9 . . ?
C10 C11 H11 120.0 . . ?
C10 C11 C12 120.1(4) . . ?
C12 C11 H11 120.0 . . ?
C11 C12 H12 119.9 . . ?
C13 C12 C11 120.2(4) . . ?
C13 C12 H12 119.9 . . ?
C8 C13 H13 120.2 . . ?
C12 C13 C8 119.6(3) . . ?
C12 C13 H13 120.2 . . ?
C15 C14 N1 120.3(3) . . ?
C15 C14 C19 120.9(3) . . ?
C19 C14 N1 118.7(3) . . ?
C14 C15 H15 120.4 . . ?
C16 C15 C14 119.3(4) . . ?
C16 C15 H15 120.4 . . ?
C15 C16 H16 119.9 . . ?
C15 C16 C17 120.2(4) . . ?
C17 C16 H16 119.9 . . ?
C16 C17 H17 119.7 . . ?
C18 C17 C16 120.7(4) . . ?
C18 C17 H17 119.7 . . ?
C17 C18 H18 119.6 . . ?
C17 C18 C19 120.8(4) . . ?
C19 C18 H18 119.6 . . ?
C14 C19 C20 119.5(3) . . ?
C18 C19 C14 118.2(4) . . ?
C18 C19 C20 122.3(3) . . ?
C19 C20 H20 115.8 . . ?
C21 C20 C19 128.4(4) . . ?
C21 C20 H20 115.8 . . ?
C20 C21 H21 119.4 . . ?
C20 C21 C22 121.1(4) . . ?
C22 C21 H21 119.4 . . ?
O1 C22 O2 122.8(4) . . ?
O1 C22 C21 126.5(4) . . ?
O2 C22 C21 110.7(4) . . ?
O2 C23 H23A 109.5 . . ?
O2 C23 H23B 109.5 . . ?
O2 C23 H23C 109.5 . . ?
H23A C23 H23B 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 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
S1 C1 C2 C3 173.7(3) . . . . ?
S1 C1 C6 C5 -172.9(3) . . . . ?
S2 C8 C9 C10 178.6(3) . . . . ?
S2 C8 C13 C12 -178.9(3) . . . . ?
N1 C14 C15 C16 -176.9(3) . . . . ?
N1 C14 C19 C18 177.2(3) . . . . ?
N1 C14 C19 C20 -2.3(5) . . . . ?
C1 S1 C7 S2 -160.55(19) . . . . ?
C1 S1 C7 N1 17.7(3) . . . . ?
C1 C2 C3 C4 -1.2(6) . . . . ?
C2 C1 C6 C5 0.6(6) . . . . ?
C2 C3 C4 C5 1.3(7) . . . . ?
C3 C4 C5 C6 -0.4(7) . . . . ?
C4 C5 C6 C1 -0.5(7) . . . . ?
C6 C1 C2 C3 0.3(6) . . . . ?
C7 S1 C1 C2 74.4(3) . . . . ?
C7 S1 C1 C6 -112.2(3) . . . . ?
C7 S2 C8 C9 89.0(3) . . . . ?
C7 S2 C8 C13 -94.6(3) . . . . ?
C7 N1 C14 C15 -79.1(4) . . . . ?
C7 N1 C14 C19 104.9(4) . . . . ?
C8 S2 C7 S1 -0.8(2) . . . . ?
C8 S2 C7 N1 -179.0(3) . . . . ?
C8 C9 C10 C11 -0.2(6) . . . . ?
C9 C8 C13 C12 -2.5(5) . . . . ?
C9 C10 C11 C12 -1.5(6) . . . . ?
C10 C11 C12 C13 1.3(6) . . . . ?
C11 C12 C13 C8 0.7(6) . . . . ?
C13 C8 C9 C10 2.2(5) . . . . ?
C14 N1 C7 S1 -177.1(3) . . . . ?
C14 N1 C7 S2 1.0(5) . . . . ?
C14 C15 C16 C17 0.2(6) . . . . ?
C14 C19 C20 C21 -171.9(4) . . . . ?
C15 C14 C19 C18 1.2(5) . . . . ?
C15 C14 C19 C20 -178.3(3) . . . . ?
C15 C16 C17 C18 0.4(7) . . . . ?
C16 C17 C18 C19 -0.1(7) . . . . ?
C17 C18 C19 C14 -0.7(5) . . . . ?
C17 C18 C19 C20 178.8(4) . . . . ?
C18 C19 C20 C21 8.6(6) . . . . ?
C19 C14 C15 C16 -1.0(5) . . . . ?
C19 C20 C21 C22 -179.1(3) . . . . ?
C20 C21 C22 O1 -1.7(7) . . . . ?
C20 C21 C22 O2 179.4(3) . . . . ?
C23 O2 C22 O1 0.9(6) . . . . ?
C23 O2 C22 C21 179.8(3) . . . . ?

_shelx_SHELXL_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'
