# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2021

####################################################################### 
# 
# 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_IL-9
_database_code_depnum_ccdc_archive 'CCDC 1959600'
_audit_update_record             
;
2019-10-16 deposited with the CCDC.	2021-03-10 downloaded from the CCDC.
;
_audit_creation_date             2019-10-16
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_chemical_formula_moiety         '4(C14 Cl N2 O3)'
_chemical_formula_sum            'C56 Cl4 N8 O12'
_chemical_formula_weight         1118.48
_chemical_oxdiff_formula         'C14 H15 Cl N2 O3'
_chemical_oxdiff_usercomment     07-010-2019
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x,-y,-z

_symmetry_Int_Tables_number      2
_cell_length_a                   12.4372(5)
_cell_length_b                   7.2932(2)
_cell_length_c                   16.2417(6)
_cell_angle_alpha                90
_cell_angle_beta                 108.876(4)
_cell_angle_gamma                90
_cell_volume                     1394.01(9)
_cell_formula_units_Z            1
_cell_measurement_reflns_used    4183
_cell_measurement_temperature    298.8(6)
_cell_measurement_theta_max      27.6000
_cell_measurement_theta_min      3.6090
_exptl_absorpt_coefficient_mu    0.280
_exptl_absorpt_correction_type   none
_exptl_crystal_density_diffrn    1.3322
_exptl_crystal_F_000             556.8877
_diffrn_reflns_av_R_equivalents  0.0810
_diffrn_reflns_av_unetI/netI     0.0717
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            21213
_diffrn_reflns_theta_full        29.6046
_diffrn_reflns_theta_max         29.60
_diffrn_reflns_theta_min         3.33
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      298.8(6)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 15.9853
_diffrn_detector_type            Sapphire3
_diffrn_measured_fraction_theta_full 0.8715
_diffrn_measured_fraction_theta_max 0.8715
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -11.00  25.00   1.00    2.00    --  -14.36 -99.00 -30.00   36
  2  ω    -22.00  42.00   1.00    2.00    --  -14.36  57.00  60.00   64
  3  ω      2.00  86.00   1.00    2.00    --   18.43  57.00 120.00   84
  4  ω    -39.00  45.00   1.00    2.00    --   18.43 -77.00 -30.00   84
  5  ω    -19.00  57.00   1.00    2.00    --   18.43 -99.00-120.00   76
  6  ω      6.00  86.00   1.00    2.00    --   18.43  57.00 -60.00   80
  7  ω      3.00  80.00   1.00    2.00    --   18.43  57.00-150.00   77
  8  ω     -7.00  85.00   1.00    2.00    --   18.43  19.00  60.00   92
  9  ω     -3.00  67.00   1.00    2.00    --   18.43-116.00 127.54   70
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Sapphire3'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0541936000
_diffrn_orient_matrix_UB_12      -0.0119236000
_diffrn_orient_matrix_UB_13      -0.0317637000
_diffrn_orient_matrix_UB_21      0.0263502000
_diffrn_orient_matrix_UB_22      -0.0222075000
_diffrn_orient_matrix_UB_23      -0.0314716000
_diffrn_orient_matrix_UB_31      0.0006619000
_diffrn_orient_matrix_UB_32      -0.0939206000
_diffrn_orient_matrix_UB_33      0.0114742000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              15
_reflns_limit_h_min              -16
_reflns_limit_k_max              10
_reflns_limit_k_min              -9
_reflns_limit_l_max              22
_reflns_limit_l_min              0
_reflns_number_gt                4282
_reflns_number_total             6822
_reflns_odcompleteness_completeness 99.68
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_threshold_expression     I>=2u(I)
_computing_cell_refinement       'CrysAlisPro 1.171.40.61a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.61a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.61a (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine (Bourhis et al., 2015)'
_computing_structure_solution    'olex2.solve (Bourhis et al., 2015)'
_refine_diff_density_max         3.0207
_refine_diff_density_min         -3.0934
_refine_diff_density_rms         0.2096
_refine_ls_d_res_high            0.7193
_refine_ls_d_res_low             6.1225
_refine_ls_goodness_of_fit_ref   2.6068
_refine_ls_hydrogen_treatment    undef
_refine_ls_matrix_type           full
_refine_ls_number_constraints    0
_refine_ls_number_parameters     161
_refine_ls_number_reflns         6822
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.2272
_refine_ls_R_factor_gt           0.1831
_refine_ls_restrained_S_all      2.6068
_refine_ls_shift/su_max          0.7017
_refine_ls_shift/su_mean         0.2042
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.4501
_refine_ls_wR_factor_ref         0.4857
_olex2_refinement_description    
;
;
_atom_sites_solution_primary     iterative
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_refinement_flags_posn
Cl01 Cl 1.0561(2) -0.1519(3) 0.60718(17) 0.0809(8) Uiso 1.000000 .
Cl02 Cl 0.4435(2) 0.3481(3) 0.89313(17) 0.0785(8) Uiso 1.000000 .
O003 O 0.7707(4) 0.9481(6) 0.7595(3) 0.0411(11) Uiso 1.000000 .
O004 O 0.7293(4) 0.4484(6) 0.7399(3) 0.0412(11) Uiso 1.000000 .
O005 O 0.2997(4) 0.7635(6) 0.5123(3) 0.0435(11) Uiso 1.000000 .
O006 O 1.2007(4) 0.2633(6) 0.9876(3) 0.0431(11) Uiso 1.000000 .
O007 O 1.2145(4) 0.5592(7) 1.0173(3) 0.0532(13) Uiso 1.000000 .
O008 O 0.2854(4) 1.0591(7) 0.4828(3) 0.0554(14) Uiso 1.000000 .
N009 N 0.6134(4) 0.7857(7) 0.6888(3) 0.0330(12) Uiso 1.000000 .
N00A N 0.8905(4) 0.6034(7) 0.8158(3) 0.0338(12) Uiso 1.000000 .
N00B N 0.8871(4) 0.2866(7) 0.8119(3) 0.0337(12) Uiso 1.000000 .
N00C N 0.6097(4) 1.1036(7) 0.6843(3) 0.0365(12) Uiso 1.000000 .
C00D C 0.8317(5) 0.4426(8) 0.7866(4) 0.0346(14) Uiso 1.000000 .
C00E C 0.4391(5) 0.7529(8) 0.7280(4) 0.0312(13) Uiso 1.000000 .
C00F C 0.4873(5) 0.7786(8) 0.6539(4) 0.0323(13) Uiso 1.000000 .
C00G C 0.4446(5) 0.9465(7) 0.5985(4) 0.0297(13) Uiso 1.000000 .
C00H C 0.6684(5) 0.9428(8) 0.7138(4) 0.0341(14) Uiso 1.000000 .
C00I C 1.0553(5) 0.4490(8) 0.9008(4) 0.0305(13) Uiso 1.000000 .
C00J C 1.0607(5) 0.2526(8) 0.7727(4) 0.0323(13) Uiso 1.000000 .
C00K C 0.5057(5) 1.1057(8) 0.6183(4) 0.0323(13) Uiso 1.000000 .
C00L C 0.9948(5) 0.6049(8) 0.8823(4) 0.0333(14) Uiso 1.000000 .
C00M C 1.0126(5) 0.2790(8) 0.8468(4) 0.0334(14) Uiso 1.000000 .
C00N C 1.1629(5) 0.4355(8) 0.9735(4) 0.0352(14) Uiso 1.000000 .
C00O C 0.3381(5) 0.9354(8) 0.5266(4) 0.0352(14) Uiso 1.000000 .
C00P C 1.0414(6) 0.0844(9) 0.7286(4) 0.0431(16) Uiso 1.000000 .
C00Q C 0.4586(6) 0.5862(9) 0.7700(4) 0.0410(15) Uiso 1.000000 .
C00R C 0.4741(6) 1.2850(9) 0.5753(4) 0.0454(17) Uiso 1.000000 .
C00S C 1.0262(6) 0.7857(10) 0.9254(5) 0.0474(17) Uiso 1.000000 .
C00T C 0.3773(6) 0.8871(10) 0.7515(5) 0.0475(17) Uiso 1.000000 .
C00U C 1.1228(6) 0.3872(10) 0.7484(5) 0.0479(17) Uiso 1.000000 .
C00V C 1.0831(6) 0.0583(10) 0.6608(5) 0.0479(17) Uiso 1.000000 .
C00W C 1.3070(6) 0.2355(10) 1.0596(5) 0.0473(17) Uiso 1.000000 .
C00X C 1.1445(7) 0.1909(10) 0.6357(5) 0.0521(18) Uiso 1.000000 .
C00Y C 0.1936(6) 0.7368(9) 0.4409(5) 0.0452(17) Uiso 1.000000 .
C00Z C 0.4177(6) 0.5590(10) 0.8385(5) 0.0473(17) Uiso 1.000000 .
C010 C 0.3552(7) 0.6915(11) 0.8635(5) 0.056(2) Uiso 1.000000 .
C011 C 0.3354(6) 0.8545(10) 0.8218(5) 0.0500(18) Uiso 1.000000 .
C012 C 1.1644(6) 0.3545(10) 0.6780(5) 0.0496(18) Uiso 1.000000 .
C013 C 0.1657(8) 0.5346(12) 0.4411(6) 0.070(2) Uiso 1.000000 .
C014 C 1.3342(8) 0.0338(13) 1.0587(6) 0.074(3) Uiso 1.000000 .

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
Cl01 C00V 1.741(8) . ?
Cl02 C00Z 1.753(7) . ?
O003 C00H 1.250(7) . ?
O004 C00D 1.255(7) . ?
O005 C00O 1.335(7) . ?
O005 C00Y 1.461(8) . ?
O006 C00N 1.335(7) . ?
O006 C00W 1.469(8) . ?
O007 C00N 1.199(7) . ?
O008 C00O 1.203(7) . ?
N009 C00F 1.487(8) . ?
N009 C00H 1.328(7) . ?
N00A C00D 1.382(8) . ?
N00A C00L 1.394(7) . ?
N00B C00D 1.325(8) . ?
N00B C00M 1.480(8) . ?
N00C C00H 1.383(8) . ?
N00C C00K 1.388(8) . ?
C00E C00F 1.520(9) . ?
C00E C00Q 1.377(9) . ?
C00E C00T 1.372(9) . ?
C00F C00G 1.510(8) . ?
C00G C00K 1.368(8) . ?
C00G C00O 1.457(8) . ?
C00I C00L 1.343(8) . ?
C00I C00M 1.512(8) . ?
C00I C00N 1.473(8) . ?
C00J C00M 1.520(9) . ?
C00J C00P 1.401(9) . ?
C00J C00U 1.383(9) . ?
C00K C00R 1.474(9) . ?
C00L C00S 1.484(9) . ?
C00P C00V 1.374(10) . ?
C00Q C00Z 1.380(10) . ?
C00T C011 1.422(10) . ?
C00U C012 1.420(10) . ?
C00V C00X 1.373(10) . ?
C00W C014 1.511(12) . ?
C00X C012 1.359(10) . ?
C00Y C013 1.515(11) . ?
C00Z C010 1.381(11) . ?
C010 C011 1.351(10) . ?

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
C00Y O005 C00O 116.4(5) . . ?
C00W O006 C00N 116.3(5) . . ?
C00H N009 C00F 121.5(5) . . ?
C00L N00A C00D 122.0(5) . . ?
C00M N00B C00D 122.0(5) . . ?
C00K N00C C00H 122.2(5) . . ?
N00A C00D O004 120.0(5) . . ?
N00B C00D O004 122.7(5) . . ?
N00B C00D N00A 117.3(5) . . ?
C00Q C00E C00F 116.7(5) . . ?
C00T C00E C00F 122.1(6) . . ?
C00T C00E C00Q 121.1(6) . . ?
C00E C00F N009 109.9(5) . . ?
C00G C00F N009 108.9(5) . . ?
C00G C00F C00E 114.8(5) . . ?
C00K C00G C00F 119.2(5) . . ?
C00O C00G C00F 119.1(5) . . ?
C00O C00G C00K 121.8(5) . . ?
N009 C00H O003 122.2(5) . . ?
N00C C00H O003 120.1(5) . . ?
N00C C00H N009 117.7(5) . . ?
C00M C00I C00L 119.9(5) . . ?
C00N C00I C00L 122.3(5) . . ?
C00N C00I C00M 117.9(5) . . ?
C00P C00J C00M 118.0(5) . . ?
C00U C00J C00M 122.3(6) . . ?
C00U C00J C00P 119.7(6) . . ?
C00G C00K N00C 118.7(5) . . ?
C00R C00K N00C 114.5(5) . . ?
C00R C00K C00G 126.8(5) . . ?
C00I C00L N00A 118.7(5) . . ?
C00S C00L N00A 114.2(5) . . ?
C00S C00L C00I 127.1(6) . . ?
C00I C00M N00B 108.7(5) . . ?
C00J C00M N00B 109.7(5) . . ?
C00J C00M C00I 114.1(5) . . ?
O007 C00N O006 121.0(6) . . ?
C00I C00N O006 112.2(5) . . ?
C00I C00N O007 126.8(6) . . ?
O008 C00O O005 120.3(6) . . ?
C00G C00O O005 111.9(5) . . ?
C00G C00O O008 127.8(6) . . ?
C00V C00P C00J 118.9(6) . . ?
C00Z C00Q C00E 118.4(6) . . ?
C011 C00T C00E 119.2(6) . . ?
C012 C00U C00J 119.5(6) . . ?
C00P C00V Cl01 117.5(5) . . ?
C00X C00V Cl01 120.5(6) . . ?
C00X C00V C00P 122.1(7) . . ?
C014 C00W O006 105.9(6) . . ?
C012 C00X C00V 119.7(7) . . ?
C013 C00Y O005 106.1(6) . . ?
C00Q C00Z Cl02 118.6(6) . . ?
C010 C00Z Cl02 119.6(6) . . ?
C010 C00Z C00Q 121.7(7) . . ?
C011 C010 C00Z 119.8(7) . . ?
C010 C011 C00T 119.7(7) . . ?
C00X C012 C00U 120.0(7) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
;
_oxdiff_exptl_absorpt_empirical_full_max 1.145
_oxdiff_exptl_absorpt_empirical_full_min 0.776
####################################################################### 
# 
# 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_thia-18
_database_code_depnum_ccdc_archive 'CCDC 1963534'
_audit_update_record             
;
2019-11-04 deposited with the CCDC.	2021-03-10 downloaded from the CCDC.
;
_audit_creation_date             2019-11-03
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '0.25(C11 H13 N2 O2 S), 0.25(C11 H12 N2 O2 S)'
_chemical_formula_sum            'C5.50 H6.25 N O S0.50'
_chemical_formula_weight         118.39
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C11 H12 N2 O2 S'
_chemical_oxdiff_usercomment     19-07-2018
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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.2836(4)
_cell_length_b                   12.2470(7)
_cell_length_c                   13.7125(8)
_cell_angle_alpha                75.781(5)
_cell_angle_beta                 74.928(5)
_cell_angle_gamma                89.897(5)
_cell_volume                     1142.40(12)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    4291
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      28.1240
_cell_measurement_theta_min      3.6870
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.270
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.79538
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.377
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       ?
_exptl_crystal_F_000             498
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0281
_diffrn_reflns_av_unetI/netI     0.0385
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.874
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            17516
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.874
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.385
_diffrn_reflns_theta_min         3.275
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 15.9853
_diffrn_detector_type            Sapphire3
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.874
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω      7.00  53.00   1.00    2.50    --  -15.32  57.00 -30.00   46
  2  ω    -46.00  29.00   1.00    2.50    --   19.00 -38.00  90.00   75
  3  ω    -25.00  59.00   1.00    2.50    --   19.00 -99.00  60.00   84
  4  ω    -25.00  59.00   1.00    2.50    --   19.00 -99.00 -60.00   84
  5  ω    -19.00  59.00   1.00    2.50    --   19.00 -99.00-150.00   78
  6  ω    -84.00   3.00   1.00    2.50    --  -15.32 -57.00  60.00   87
  7  ω    -84.00  -2.00   1.00    2.50    --  -15.32 -57.00-120.00   82
  8  ω    -84.00 -16.00   1.00    2.50    --  -15.32 -57.00-180.00   68
  9  ω    -84.00   3.00   1.00    2.50    --  -15.32 -57.00 -30.00   87
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Sapphire3'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0210124000
_diffrn_orient_matrix_UB_12      0.0574038000
_diffrn_orient_matrix_UB_13      -0.0139848000
_diffrn_orient_matrix_UB_21      0.0006188000
_diffrn_orient_matrix_UB_22      0.0051765000
_diffrn_orient_matrix_UB_23      0.0503116000
_diffrn_orient_matrix_UB_31      0.0988641000
_diffrn_orient_matrix_UB_32      0.0162263000
_diffrn_orient_matrix_UB_33      -0.0184480000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4008
_reflns_number_total             5494
_reflns_odcompleteness_completeness 99.61
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'olex2.solve (Bourhis et al., 2015)'
_refine_diff_density_max         0.194
_refine_diff_density_min         -0.571
_refine_diff_density_rms         0.047
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     298
_refine_ls_number_reflns         5494
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0766
_refine_ls_R_factor_gt           0.0531
_refine_ls_restrained_S_all      1.038
_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)+(0.0504P)²+0.3697P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1176
_refine_ls_wR_factor_ref         0.1329
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups, All N(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Rotating group:
 N009(H00I)
2.b Aromatic/amide H refined with riding coordinates:
 N003(H003), C2(H2), C00K(H00K), C00L(H00L), C4(H4), C3(H3), C00Q(H00Q),
 C00R(H00R), C00S(H00S)
2.c X=CH2 refined with riding coordinates:
 N006(H00A,H00B)
2.d Idealised Me refined as rotating group:
 C00T(H00C,H00D,H00E), C00U(H00F,H00G,H00H), C00V(H00M,H00N,H00O), C00W(H00P,
 H00T,H00U)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     iterative
_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
S001 S -0.11615(9) 1.11581(6) 0.23447(4) 0.05668(19) Uani 1 1 d . . . . .
S002 S 0.61392(9) 0.73386(6) 0.76723(5) 0.0612(2) Uani 1 1 d . . . . .
N003 N 0.0925(2) 1.01267(13) 0.34685(11) 0.0349(3) Uani 1 1 d . . . . .
H003 H 0.140941 0.987831 0.398344 0.042 Uiso 1 1 calc R . . . .
N004 N 0.3927(2) 0.71352(14) 0.65328(12) 0.0402(4) Uani 1 1 d . . . . .
O005 O 0.2806(2) 0.90020(16) 0.07180(12) 0.0660(5) Uani 1 1 d . . . . .
N006 N -0.1336(2) 1.11896(15) 0.43116(12) 0.0463(4) Uani 1 1 d . . . . .
H00A H -0.097645 1.100732 0.487694 0.056 Uiso 1 1 calc R . . . .
H00B H -0.225195 1.162768 0.427129 0.056 Uiso 1 1 calc R . . . .
O007 O 0.6645(3) 0.80980(16) 0.37644(13) 0.0716(5) Uani 1 1 d . . . . .
O008 O 0.1875(3) 0.44001(15) 0.91894(13) 0.0736(5) Uani 1 1 d . . . . .
N009 N 0.6202(3) 0.86621(18) 0.57789(15) 0.0570(5) Uani 1 1 d . . . . .
H00I H 0.601106 0.860799 0.519719 0.068 Uiso 1 1 d GR . . . .
O00A O -0.1601(3) 0.54006(16) 0.59848(16) 0.0819(6) Uani 1 1 d . . . . .
C00B C -0.0468(3) 1.07912(15) 0.34939(13) 0.0344(4) Uani 1 1 d . . . . .
C1 C 0.3170(3) 0.91568(16) 0.23470(14) 0.0390(4) Uani 1 1 d . . . . .
C00D C 0.1540(3) 0.98643(16) 0.25082(14) 0.0375(4) Uani 1 1 d . . . . .
C2 C 0.4196(3) 0.89040(17) 0.30831(15) 0.0439(5) Uani 1 1 d . . . . .
H2 H 0.380914 0.917021 0.367933 0.053 Uiso 1 1 calc R . . . .
C00F C 0.5369(3) 0.77528(18) 0.65493(15) 0.0414(5) Uani 1 1 d . . . . .
C00G C 0.3350(3) 0.62681(17) 0.74441(15) 0.0425(5) Uani 1 1 d . . . . .
C00H C 0.1686(3) 0.55215(17) 0.75490(16) 0.0455(5) Uani 1 1 d . . . . .
C5 C 0.3799(3) 0.87380(19) 0.14544(16) 0.0471(5) Uani 1 1 d . . . . .
C00J C 0.5774(3) 0.82713(19) 0.29674(16) 0.0491(5) Uani 1 1 d . . . . .
C00K C 0.0561(3) 1.0349(2) 0.18215(16) 0.0535(6) Uani 1 1 d . . . . .
H00K H 0.079158 1.025676 0.114793 0.064 Uiso 1 1 calc R . . . .
C00L C 0.0766(3) 0.57252(18) 0.67632(18) 0.0501(5) Uani 1 1 d . . . . .
H00L H 0.124732 0.631630 0.617473 0.060 Uiso 1 1 calc R . . . .
C00M C 0.0940(3) 0.46095(19) 0.84227(18) 0.0564(6) Uani 1 1 d . . . . .
C4 C 0.5367(4) 0.8107(2) 0.13491(18) 0.0589(6) Uani 1 1 d . . . . .
H4 H 0.576632 0.783339 0.075776 0.071 Uiso 1 1 calc R . . . .
C00O C -0.0837(3) 0.50873(19) 0.6816(2) 0.0578(6) Uani 1 1 d . . . . .
C3 C 0.6365(3) 0.7868(2) 0.20945(19) 0.0587(6) Uani 1 1 d . . . . .
H3 H 0.742427 0.744068 0.200732 0.070 Uiso 1 1 calc R . . . .
C00Q C 0.4378(4) 0.6269(2) 0.81358(18) 0.0592(6) Uani 1 1 d . . . . .
H00Q H 0.415617 0.575177 0.878340 0.071 Uiso 1 1 calc R . . . .
C00R C -0.1562(4) 0.4213(2) 0.7677(2) 0.0703(7) Uani 1 1 d . . . . .
H00R H -0.265056 0.378245 0.772946 0.084 Uiso 1 1 calc R . . . .
C00S C -0.0661(4) 0.3979(2) 0.8465(2) 0.0721(8) Uani 1 1 d . . . . .
H00S H -0.114517 0.337668 0.904288 0.087 Uiso 1 1 calc R . . . .
C00T C 0.3557(4) 0.8731(3) -0.02505(18) 0.0731(8) Uani 1 1 d . . . . .
H00C H 0.279745 0.903667 -0.071723 0.110 Uiso 1 1 calc GR . . . .
H00D H 0.353678 0.792551 -0.014039 0.110 Uiso 1 1 calc GR . . . .
H00E H 0.484533 0.904698 -0.054963 0.110 Uiso 1 1 calc GR . . . .
C00U C 0.8200(4) 0.7394(3) 0.3716(2) 0.0777(8) Uani 1 1 d . . . . .
H00F H 0.921749 0.772676 0.310945 0.117 Uiso 1 1 calc GR . . . .
H00G H 0.779554 0.666455 0.367437 0.117 Uiso 1 1 calc GR . . . .
H00H H 0.863653 0.731316 0.433121 0.117 Uiso 1 1 calc GR . . . .
C00V C 0.1073(5) 0.3527(2) 1.0113(2) 0.0868(10) Uani 1 1 d . . . . .
H00M H 0.107837 0.281419 0.993836 0.130 Uiso 1 1 calc GR . . . .
H00N H -0.021248 0.367852 1.041999 0.130 Uiso 1 1 calc GR . . . .
H00O H 0.181618 0.350086 1.060245 0.130 Uiso 1 1 calc GR . . . .
C00W C -0.3107(5) 0.4686(3) 0.5950(3) 0.0962(10) Uani 1 1 d . . . . .
H00P H -0.344657 0.496482 0.530619 0.144 Uiso 1 1 calc GR . . . .
H00T H -0.419296 0.467688 0.652648 0.144 Uiso 1 1 calc GR . . . .
H00U H -0.269804 0.393415 0.599278 0.144 Uiso 1 1 calc GR . . . .
H00J H 0.710(4) 0.902(2) 0.5887(18) 0.060(7) 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
S001 C00B 1.7336(18) . ?
S001 C00K 1.717(2) . ?
S002 C00F 1.7344(19) . ?
S002 C00Q 1.715(3) . ?
N003 H003 0.8600 . ?
N003 C00B 1.298(2) . ?
N003 C00D 1.392(2) . ?
N004 C00F 1.303(2) . ?
N004 C00G 1.394(2) . ?
O005 C5 1.366(3) . ?
O005 C00T 1.418(3) . ?
N006 H00A 0.8600 . ?
N006 H00B 0.8600 . ?
N006 C00B 1.339(2) . ?
O007 C00J 1.374(3) . ?
O007 C00U 1.420(3) . ?
O008 C00M 1.369(3) . ?
O008 C00V 1.429(3) . ?
N009 H00I 0.8624 . ?
N009 C00F 1.347(3) . ?
N009 H00J 0.85(3) . ?
O00A C00O 1.367(3) . ?
O00A C00W 1.422(3) . ?
C1 C00D 1.471(3) . ?
C1 C2 1.382(3) . ?
C1 C5 1.410(3) . ?
C00D C00K 1.349(3) . ?
C2 H2 0.9300 . ?
C2 C00J 1.382(3) . ?
C00G C00H 1.475(3) . ?
C00G C00Q 1.352(3) . ?
C00H C00L 1.384(3) . ?
C00H C00M 1.409(3) . ?
C5 C4 1.374(3) . ?
C00J C3 1.372(3) . ?
C00K H00K 0.9300 . ?
C00L H00L 0.9300 . ?
C00L C00O 1.383(3) . ?
C00M C00S 1.381(4) . ?
C4 H4 0.9300 . ?
C4 C3 1.377(3) . ?
C00O C00R 1.370(3) . ?
C3 H3 0.9300 . ?
C00Q H00Q 0.9300 . ?
C00R H00R 0.9300 . ?
C00R C00S 1.376(4) . ?
C00S H00S 0.9300 . ?
C00T H00C 0.9600 . ?
C00T H00D 0.9600 . ?
C00T H00E 0.9600 . ?
C00U H00F 0.9600 . ?
C00U H00G 0.9600 . ?
C00U H00H 0.9600 . ?
C00V H00M 0.9600 . ?
C00V H00N 0.9600 . ?
C00V H00O 0.9600 . ?
C00W H00P 0.9600 . ?
C00W H00T 0.9600 . ?
C00W H00U 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
C00K S001 C00B 88.80(9) . . ?
C00Q S002 C00F 88.60(10) . . ?
C00B N003 H003 124.0 . . ?
C00B N003 C00D 111.95(15) . . ?
C00D N003 H003 124.0 . . ?
C00F N004 C00G 111.10(16) . . ?
C5 O005 C00T 118.4(2) . . ?
H00A N006 H00B 120.0 . . ?
C00B N006 H00A 120.0 . . ?
C00B N006 H00B 120.0 . . ?
C00J O007 C00U 117.79(19) . . ?
C00M O008 C00V 117.9(2) . . ?
H00I N009 H00J 129.6 . . ?
C00F N009 H00I 109.9 . . ?
C00F N009 H00J 115.8(16) . . ?
C00O O00A C00W 117.6(2) . . ?
N003 C00B S001 114.17(14) . . ?
N003 C00B N006 125.19(16) . . ?
N006 C00B S001 120.64(14) . . ?
C2 C1 C00D 119.50(17) . . ?
C2 C1 C5 117.08(19) . . ?
C5 C1 C00D 123.40(18) . . ?
N003 C00D C1 118.15(16) . . ?
C00K C00D N003 113.42(18) . . ?
C00K C00D C1 128.38(18) . . ?
C1 C2 H2 118.7 . . ?
C00J C2 C1 122.56(19) . . ?
C00J C2 H2 118.7 . . ?
N004 C00F S002 114.77(15) . . ?
N004 C00F N009 124.07(18) . . ?
N009 C00F S002 121.14(16) . . ?
N004 C00G C00H 117.07(17) . . ?
C00Q C00G N004 113.81(19) . . ?
C00Q C00G C00H 129.05(19) . . ?
C00L C00H C00G 119.18(18) . . ?
C00L C00H C00M 117.2(2) . . ?
C00M C00H C00G 123.6(2) . . ?
O005 C5 C1 117.19(19) . . ?
O005 C5 C4 122.95(19) . . ?
C4 C5 C1 119.9(2) . . ?
O007 C00J C2 115.57(18) . . ?
C3 C00J O007 124.8(2) . . ?
C3 C00J C2 119.6(2) . . ?
S001 C00K H00K 124.2 . . ?
C00D C00K S001 111.65(15) . . ?
C00D C00K H00K 124.2 . . ?
C00H C00L H00L 118.6 . . ?
C00O C00L C00H 122.8(2) . . ?
C00O C00L H00L 118.6 . . ?
O008 C00M C00H 117.0(2) . . ?
O008 C00M C00S 123.7(2) . . ?
C00S C00M C00H 119.4(2) . . ?
C5 C4 H4 119.1 . . ?
C5 C4 C3 121.9(2) . . ?
C3 C4 H4 119.1 . . ?
O00A C00O C00L 116.0(2) . . ?
O00A C00O C00R 124.7(2) . . ?
C00R C00O C00L 119.3(2) . . ?
C00J C3 C4 119.0(2) . . ?
C00J C3 H3 120.5 . . ?
C4 C3 H3 120.5 . . ?
S002 C00Q H00Q 124.1 . . ?
C00G C00Q S002 111.70(17) . . ?
C00G C00Q H00Q 124.1 . . ?
C00O C00R H00R 120.4 . . ?
C00O C00R C00S 119.2(2) . . ?
C00S C00R H00R 120.4 . . ?
C00M C00S H00S 119.0 . . ?
C00R C00S C00M 122.0(2) . . ?
C00R C00S H00S 119.0 . . ?
O005 C00T H00C 109.5 . . ?
O005 C00T H00D 109.5 . . ?
O005 C00T H00E 109.5 . . ?
H00C C00T H00D 109.5 . . ?
H00C C00T H00E 109.5 . . ?
H00D C00T H00E 109.5 . . ?
O007 C00U H00F 109.5 . . ?
O007 C00U H00G 109.5 . . ?
O007 C00U H00H 109.5 . . ?
H00F C00U H00G 109.5 . . ?
H00F C00U H00H 109.5 . . ?
H00G C00U H00H 109.5 . . ?
O008 C00V H00M 109.5 . . ?
O008 C00V H00N 109.5 . . ?
O008 C00V H00O 109.5 . . ?
H00M C00V H00N 109.5 . . ?
H00M C00V H00O 109.5 . . ?
H00N C00V H00O 109.5 . . ?
O00A C00W H00P 109.5 . . ?
O00A C00W H00T 109.5 . . ?
O00A C00W H00U 109.5 . . ?
H00P C00W H00T 109.5 . . ?
H00P C00W H00U 109.5 . . ?
H00T C00W H00U 109.5 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.191
_oxdiff_exptl_absorpt_empirical_full_min 0.595
