# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 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_twin_twin1_hklf4
_database_code_depnum_ccdc_archive 'CCDC 1500325'
_audit_update_record             
;
2016-08-22 deposited with the CCDC.
2017-04-21 downloaded from the CCDC.
;
_audit_creation_date             2016-03-22
_audit_creation_method           
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C19 H15 Cl N2 O4, C H2 Cl2'
_chemical_formula_sum            'C20 H17 Cl3 N2 O4'
_chemical_formula_weight         455.71
_chemical_melting_point          ?
_chemical_oxdiff_formula         c8h4o4n2
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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, y+1/2, -z+1/2'
3 '-x, -y, -z'
4 'x, -y-1/2, z-1/2'

_cell_length_a                   14.3285(16)
_cell_length_b                   9.7542(4)
_cell_length_c                   21.475(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 136.08(2)
_cell_angle_gamma                90.00
_cell_volume                     2081.9(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2179
_cell_measurement_temperature    142.95(10)
_cell_measurement_theta_max      27.4520
_cell_measurement_theta_min      3.4340
_exptl_absorpt_coefficient_mu    0.470
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.94036
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.41 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.454
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             936
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.3
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0000
_diffrn_reflns_av_unetI/netI     0.0508
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            8491
_diffrn_reflns_theta_full        26.37
_diffrn_reflns_theta_max         26.37
_diffrn_reflns_theta_min         2.93
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      142.95(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0874
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -21.00  10.00   1.00    7.50    --  -14.97 -99.00-150.00   31
  2  ω    -47.00  45.00   1.00    7.50    --   16.69 -19.00  30.00   92
  3  ω    -52.00  32.00   1.00    7.50    --   16.69 -19.00 -60.00   84
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0407074000
_diffrn_orient_matrix_UB_12      -0.0112349000
_diffrn_orient_matrix_UB_13      0.0070693000
_diffrn_orient_matrix_UB_21      0.0428028000
_diffrn_orient_matrix_UB_22      -0.0545278000
_diffrn_orient_matrix_UB_23      0.0298331000
_diffrn_orient_matrix_UB_31      0.0400471000
_diffrn_orient_matrix_UB_32      0.0467860000
_diffrn_orient_matrix_UB_33      0.0364481000
_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'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                4598
_reflns_number_total             8491
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41 (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    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.525
_refine_diff_density_min         -0.627
_refine_diff_density_rms         0.063
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.912
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     271
_refine_ls_number_reflns         8491
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1030
_refine_ls_R_factor_gt           0.0590
_refine_ls_restrained_S_all      0.912
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.1059P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1612
_refine_ls_wR_factor_ref         0.1755
_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. 
;
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 0.5891(10) 0.4109(10)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
3.a Ternary CH refined with riding coordinates:
 C11(H11)
3.b Secondary CH2 refined with riding coordinates:
 C10(H10A,H10B), C20(H20A,H20B)
3.c Aromatic/amide H refined with riding coordinates:
 N2(H2), C2(H2A), C5(H5), C6(H6), C7(H7), C8(H8), C15(H15), C16(H16), C18(H18),
  C19(H19)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
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_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_refinement_flags_posn
Cl1 Cl 0.44575(8) 0.27972(12) 0.39439(5) 0.1107(4) Uani 1 d . . .
O1 O 0.60502(13) 0.63500(12) 0.82879(9) 0.0434(4) Uani 1 d . . .
O2 O 0.85501(15) 0.03512(18) 0.81047(10) 0.0607(5) Uani 1 d . . .
O3 O 0.85392(14) -0.12788(13) 0.96695(9) 0.0510(5) Uani 1 d . . .
O4 O 0.65480(14) -0.12048(15) 0.82547(9) 0.0564(5) Uani 1 d . . .
H4 H 0.643(2) -0.209(3) 0.8320(16) 0.071(8) Uiso 1 d . . .
N1 N 0.81476(16) 0.58810(17) 0.96497(10) 0.0332(4) Uani 1 d . . .
H1 H 0.830(2) 0.677(2) 0.9700(15) 0.058(7) Uiso 1 d . . .
N2 N 0.70155(16) 0.12935(14) 0.80026(10) 0.0316(4) Uani 1 d . . .
H2 H 0.6262 0.1759 0.7681 0.038 Uiso 1 calc . . R
C1 C 0.69146(19) 0.54824(19) 0.88822(13) 0.0323(5) Uani 1 d . . .
C2 C 0.66408(18) 0.40460(18) 0.87774(12) 0.0331(5) Uani 1 d . . .
H2A H 0.5764 0.3732 0.8252 0.040 Uiso 1 calc . . R
C3 C 0.75819(19) 0.31182(18) 0.93973(12) 0.0294(5) Uani 1 d . . .
C4 C 0.89068(19) 0.35918(18) 1.02052(12) 0.0305(5) Uani 1 d . . .
C5 C 0.9973(2) 0.2720(2) 1.09025(13) 0.0403(5) Uani 1 d . . .
H5 H 0.9832 0.1757 1.0848 0.048 Uiso 1 calc . . R
C6 C 1.1192(2) 0.3236(2) 1.16468(13) 0.0474(6) Uani 1 d . . .
H6 H 1.1893 0.2633 1.2108 0.057 Uiso 1 calc . . R
C7 C 1.1423(2) 0.4644(2) 1.17399(14) 0.0487(6) Uani 1 d . . .
H7 H 1.2283 0.4993 1.2264 0.058 Uiso 1 calc . . R
C8 C 1.0425(2) 0.5529(2) 1.10845(13) 0.0398(5) Uani 1 d . . .
H8 H 1.0585 0.6489 1.1149 0.048 Uiso 1 calc . . R
C9 C 0.91641(18) 0.49979(18) 1.03180(12) 0.0304(5) Uani 1 d . . .
C10 C 0.7247(2) 0.16174(17) 0.92375(13) 0.0329(5) Uani 1 d . . .
H10A H 0.6258 0.1509 0.8787 0.040 Uiso 1 calc . . R
H10B H 0.7642 0.1189 0.9803 0.040 Uiso 1 calc . . R
C11 C 0.77646(19) 0.08637(18) 0.89081(12) 0.0304(5) Uani 1 d . . .
H11 H 0.8733 0.1105 0.9312 0.036 Uiso 1 calc . . R
C12 C 0.7664(2) -0.06610(19) 0.89829(13) 0.0333(5) Uani 1 d . . .
C13 C 0.7485(2) 0.0973(2) 0.76627(13) 0.0372(5) Uani 1 d . . .
C14 C 0.6685(2) 0.1438(2) 0.67271(13) 0.0414(5) Uani 1 d . . .
C15 C 0.5765(2) 0.2506(2) 0.63177(15) 0.0512(6) Uani 1 d . . .
H15 H 0.5601 0.2948 0.6626 0.061 Uiso 1 calc . . R
C16 C 0.5086(2) 0.2931(3) 0.54632(16) 0.0664(8) Uani 1 d . . .
H16 H 0.4462 0.3667 0.5183 0.080 Uiso 1 calc . . R
C17 C 0.5329(2) 0.2268(3) 0.50266(16) 0.0698(8) Uani 1 d . . .
C18 C 0.6221(3) 0.1214(3) 0.54122(17) 0.0716(8) Uani 1 d . . .
H18 H 0.6368 0.0766 0.5096 0.086 Uiso 1 calc . . R
C19 C 0.6907(2) 0.0807(3) 0.62664(15) 0.0595(7) Uani 1 d . . .
H19 H 0.7542 0.0082 0.6544 0.071 Uiso 1 calc . . R
Cl2 Cl 0.18809(11) 0.53831(11) 0.36461(7) 0.1180(4) Uani 1 d . . .
Cl3 Cl 0.14339(14) 0.24972(12) 0.36263(10) 0.1493(5) Uani 1 d . . .
C20 C 0.0738(3) 0.4104(5) 0.3127(3) 0.1268(14) Uani 1 d . . .
H20A H 0.0264 0.4055 0.2494 0.152 Uiso 1 calc . . R
H20B H 0.0062 0.4326 0.3126 0.152 Uiso 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
Cl1 C17 1.746(3) . ?
O1 C1 1.266(2) . ?
O2 C13 1.229(2) . ?
O3 C12 1.203(2) . ?
O4 H4 0.91(3) . ?
O4 C12 1.297(2) . ?
N1 H1 0.89(2) . ?
N1 C1 1.339(2) . ?
N1 C9 1.383(2) . ?
N2 H2 0.8800 . ?
N2 C11 1.450(2) . ?
N2 C13 1.339(3) . ?
C1 C2 1.428(3) . ?
C2 H2A 0.9500 . ?
C2 C3 1.350(2) . ?
C3 C4 1.443(3) . ?
C3 C10 1.501(3) . ?
C4 C5 1.415(3) . ?
C4 C9 1.395(2) . ?
C5 H5 0.9500 . ?
C5 C6 1.355(3) . ?
C6 H6 0.9500 . ?
C6 C7 1.393(3) . ?
C7 H7 0.9500 . ?
C7 C8 1.369(3) . ?
C8 H8 0.9500 . ?
C8 C9 1.399(3) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C10 C11 1.533(3) . ?
C11 H11 1.0000 . ?
C11 C12 1.514(3) . ?
C13 C14 1.496(3) . ?
C14 C15 1.388(3) . ?
C14 C19 1.383(3) . ?
C15 H15 0.9500 . ?
C15 C16 1.383(3) . ?
C16 H16 0.9500 . ?
C16 C17 1.374(4) . ?
C17 C18 1.361(4) . ?
C18 H18 0.9500 . ?
C18 C19 1.375(3) . ?
C19 H19 0.9500 . ?
Cl2 C20 1.689(4) . ?
Cl3 C20 1.749(4) . ?
C20 H20A 0.9900 . ?
C20 H20B 0.9900 . ?

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
C12 O4 H4 114.1(15) . . ?
C1 N1 H1 115.2(14) . . ?
C1 N1 C9 124.47(17) . . ?
C9 N1 H1 120.2(15) . . ?
C11 N2 H2 120.4 . . ?
C13 N2 H2 120.4 . . ?
C13 N2 C11 119.13(16) . . ?
O1 C1 N1 120.80(17) . . ?
O1 C1 C2 122.60(17) . . ?
N1 C1 C2 116.60(17) . . ?
C1 C2 H2A 118.8 . . ?
C3 C2 C1 122.42(17) . . ?
C3 C2 H2A 118.8 . . ?
C2 C3 C4 119.04(17) . . ?
C2 C3 C10 120.02(17) . . ?
C4 C3 C10 120.94(16) . . ?
C5 C4 C3 124.23(17) . . ?
C9 C4 C3 118.53(16) . . ?
C9 C4 C5 117.25(17) . . ?
C4 C5 H5 119.4 . . ?
C6 C5 C4 121.13(19) . . ?
C6 C5 H5 119.4 . . ?
C5 C6 H6 119.8 . . ?
C5 C6 C7 120.43(19) . . ?
C7 C6 H6 119.8 . . ?
C6 C7 H7 119.7 . . ?
C8 C7 C6 120.66(19) . . ?
C8 C7 H7 119.7 . . ?
C7 C8 H8 120.5 . . ?
C7 C8 C9 118.92(19) . . ?
C9 C8 H8 120.5 . . ?
N1 C9 C4 118.89(17) . . ?
N1 C9 C8 119.50(17) . . ?
C4 C9 C8 121.60(17) . . ?
C3 C10 H10A 109.0 . . ?
C3 C10 H10B 109.0 . . ?
C3 C10 C11 113.05(16) . . ?
H10A C10 H10B 107.8 . . ?
C11 C10 H10A 109.0 . . ?
C11 C10 H10B 109.0 . . ?
N2 C11 C10 110.10(15) . . ?
N2 C11 H11 108.6 . . ?
N2 C11 C12 113.03(15) . . ?
C10 C11 H11 108.6 . . ?
C12 C11 C10 107.92(16) . . ?
C12 C11 H11 108.6 . . ?
O3 C12 O4 124.37(18) . . ?
O3 C12 C11 121.84(17) . . ?
O4 C12 C11 113.76(16) . . ?
O2 C13 N2 121.74(19) . . ?
O2 C13 C14 120.7(2) . . ?
N2 C13 C14 117.49(19) . . ?
C15 C14 C13 122.5(2) . . ?
C19 C14 C13 118.5(2) . . ?
C19 C14 C15 118.9(2) . . ?
C14 C15 H15 119.8 . . ?
C16 C15 C14 120.3(2) . . ?
C16 C15 H15 119.8 . . ?
C15 C16 H16 120.6 . . ?
C17 C16 C15 118.9(3) . . ?
C17 C16 H16 120.6 . . ?
C16 C17 Cl1 118.7(2) . . ?
C18 C17 Cl1 119.4(2) . . ?
C18 C17 C16 121.9(2) . . ?
C17 C18 H18 120.5 . . ?
C17 C18 C19 119.0(3) . . ?
C19 C18 H18 120.5 . . ?
C14 C19 H19 119.5 . . ?
C18 C19 C14 121.0(3) . . ?
C18 C19 H19 119.5 . . ?
Cl2 C20 Cl3 113.8(2) . . ?
Cl2 C20 H20A 108.8 . . ?
Cl2 C20 H20B 108.8 . . ?
Cl3 C20 H20A 108.8 . . ?
Cl3 C20 H20B 108.8 . . ?
H20A C20 H20B 107.7 . . ?

_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 1.084
_oxdiff_exptl_absorpt_empirical_full_min 0.853
_oxdiff_twin_integration_method  simultaneous
_oxdiff_twin_items               2
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
_oxdiff_twin_reflns_isolated
_oxdiff_twin_reflns_overlapped
_twin_individual_twin_lattice_type
_twin_individual_twin_matrix_11
_twin_individual_twin_matrix_12
_twin_individual_twin_matrix_13
_twin_individual_twin_matrix_21
_twin_individual_twin_matrix_22
_twin_individual_twin_matrix_23
_twin_individual_twin_matrix_31
_twin_individual_twin_matrix_32
_twin_individual_twin_matrix_33
1 0.5891(10) 7828 1794 ref 1.0000 0.0000 0.0000 0.0000 1.0000 0.0000 0.0000
0.0000 1.0000
2 0.4109(10) 7858 1794 nmt 1.0070 0.0709 0.0087 -0.0688 0.9964 -0.0336 -0.0214
0.0016 0.9876

_twin_special_details            
;
Component 2 rotated by 4.0599° 
 around [0.44 0.06 -0.90] (reciprocal) or [0.03 0.30 -0.95] (direct)
;
####################################################################### 
# 
# 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_160413_s1_x
_database_code_depnum_ccdc_archive 'CCDC 1500324'
_audit_update_record             
;
2017-04-10 deposited with the CCDC.
2017-04-21 downloaded from the CCDC.
;
_audit_creation_date             2017-04-07
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5335)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C19 H15 Cl N2 O4, 2(C2 H6 O S)'
_chemical_formula_sum            'C23 H27 Cl N2 O6 S2'
_chemical_formula_weight         527.03
_chemical_melting_point          ?
_chemical_oxdiff_formula         c12h12n2o3cl1
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'
Cl Cl 0.1484 0.1585 '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      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   8.9468(9)
_cell_length_b                   28.971(3)
_cell_length_c                   9.8022(11)
_cell_angle_alpha                90
_cell_angle_beta                 97.029(10)
_cell_angle_gamma                90
_cell_volume                     2521.6(5)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    5436
_cell_measurement_temperature    148.00(10)
_cell_measurement_theta_max      25.5180
_cell_measurement_theta_min      3.3440
_shelx_estimated_absorpt_T_max   0.916
_shelx_estimated_absorpt_T_min   0.870
_exptl_absorpt_coefficient_mu    0.358
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.91949
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.388
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block''
_exptl_crystal_F_000             1104
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.25
_exptl_special_details           
;
 ? 
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  ?
_diffrn_reflns_av_unetI/netI     0.0601
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       36
_diffrn_reflns_limit_k_min       -36
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            9808
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.371
_diffrn_reflns_theta_min         2.972
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      148.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0874
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -30.00   14.00   0.5000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       16.6856  -57.0000  -60.0000 88

#__ type_ start__ end____ width___ exp.time_
  2 omega  -25.00   24.00   0.5000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      -14.9669  -99.0000   30.0000 98

#__ type_ start__ end____ width___ exp.time_
  3 omega   -6.00   19.00   0.5000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      -14.9669  -94.0000  131.0000 50

#__ type_ start__ end____ width___ exp.time_
  4 omega    9.00   48.00   0.5000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       16.6856  -94.0000  131.0000 78

#__ type_ start__ end____ width___ exp.time_
  5 omega  -51.00   29.00   0.5000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      -14.9669   94.0000 -117.0000 160

#__ type_ start__ end____ width___ exp.time_
  6 omega  -18.00    7.00   0.5000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       16.6856   94.0000 -117.0000 50

#__ type_ start__ end____ width___ exp.time_
  7 omega   36.00   89.00   0.5000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       16.6856  178.0000   60.0000 106

#__ type_ start__ end____ width___ exp.time_
  8 omega  -85.00  -35.00   0.5000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      -14.9669 -178.0000  -60.0000 100

#__ type_ start__ end____ width___ exp.time_
  9 omega  -87.00  -37.00   0.5000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      -14.9669 -178.0000  -30.0000 100
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0014219000
_diffrn_orient_matrix_UB_12      0.0225063000
_diffrn_orient_matrix_UB_13      0.0282855000
_diffrn_orient_matrix_UB_21      0.0774863000
_diffrn_orient_matrix_UB_22      0.0027124000
_diffrn_orient_matrix_UB_23      -0.0069532000
_diffrn_orient_matrix_UB_31      -0.0192707000
_diffrn_orient_matrix_UB_32      0.0092509000
_diffrn_orient_matrix_UB_33      -0.0668495000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                5864
_reflns_number_total             9808
_reflns_odcompleteness_completeness 99.72
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_special_details          
;
 _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, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_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    
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_refine_diff_density_max         0.464
_refine_diff_density_min         -0.564
_refine_diff_density_rms         0.077
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     317
_refine_ls_number_reflns         9808
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1231
_refine_ls_R_factor_gt           0.0772
_refine_ls_restrained_S_all      1.049
_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)+(0.1276P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2009
_refine_ls_wR_factor_ref         0.2210
_refine_special_details          
;
 Refined as a 2-component twin.
;
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 0.5146(18)
 0.4854(18)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H,H,H,H) groups, All O(H) groups
3. Uiso/Uaniso restraints and constraints
Uanis(S2A) = Uanis(S2B)
Uanis(S1A) = Uanis(S1B)
4. Others
 Sof(H22D)=Sof(H22E)=Sof(H22F)=Sof(H23F)=Sof(H23D)=Sof(H23E)=Sof(S2B)=1-FVAR(1)
 Sof(H22A)=Sof(H22B)=Sof(H22C)=Sof(H23C)=Sof(H23A)=Sof(H23B)=Sof(S2A)=FVAR(1)
 Sof(H20D)=Sof(H20E)=Sof(H20F)=Sof(H21D)=Sof(H21E)=Sof(H21F)=Sof(S1B)=1-FVAR(2)
 Sof(H20A)=Sof(H20B)=Sof(H20C)=Sof(H21A)=Sof(H21B)=Sof(H21C)=Sof(S1A)=FVAR(2)
5.a Ternary CH refined with riding coordinates:
 C11(H11)
5.b Secondary CH2 refined with riding coordinates:
 C10(H10A,H10B)
5.c Me refined with riding coordinates:
 C20(H20A,H20B,H20C), C20(H20D,H20E,H20F), C21(H21A,H21B,H21C), C21(H21D,H21E,
 H21F), C22(H22A,H22B,H22C), C22(H22D,H22E,H22F), C23(H23C,H23A,H23B), C23(H23F,
 H23D,H23E)
5.d Aromatic/amide H refined with riding coordinates:
 C2(H2), C5(H5), C6(H6), C7(H7), C8(H8), C15(H15), C16(H16), C18(H18),
 C19(H19), N1(H1), N2(H2A)
5.e Idealised tetrahedral OH refined as rotating group:
 O3(H3)
;
_atom_sites_solution_hydrogens   geom
_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
C1 C 0.1728(4) 0.52972(12) -0.0819(3) 0.0333(8) Uani 1 1 d . . . . .
C2 C 0.1433(4) 0.53299(12) 0.0584(3) 0.0361(9) Uani 1 1 d . . . . .
H2 H 0.0722 0.5550 0.0820 0.043 Uiso 1 1 calc R . . . .
C3 C 0.2136(4) 0.50565(12) 0.1579(3) 0.0326(8) Uani 1 1 d . . . . .
C4 C 0.3204(4) 0.47123(11) 0.1231(3) 0.0330(8) Uani 1 1 d . . . . .
C5 C 0.4017(4) 0.44177(12) 0.2190(4) 0.0395(9) Uani 1 1 d . . . . .
H5 H 0.3895 0.4443 0.3136 0.047 Uiso 1 1 calc R . . . .
C6 C 0.4980(5) 0.40955(13) 0.1778(4) 0.0455(10) Uani 1 1 d . . . . .
H6 H 0.5511 0.3897 0.2440 0.055 Uiso 1 1 calc R . . . .
C7 C 0.5196(5) 0.40541(13) 0.0400(4) 0.0469(10) Uani 1 1 d . . . . .
H7 H 0.5856 0.3825 0.0123 0.056 Uiso 1 1 calc R . . . .
C8 C 0.4444(4) 0.43479(12) -0.0563(4) 0.0401(9) Uani 1 1 d . . . . .
H8 H 0.4611 0.4327 -0.1500 0.048 Uiso 1 1 calc R . . . .
C9 C 0.3444(4) 0.46734(11) -0.0157(3) 0.0323(8) Uani 1 1 d . . . . .
C10 C 0.1799(4) 0.51112(12) 0.3036(3) 0.0368(9) Uani 1 1 d . . . . .
H10A H 0.1814 0.4803 0.3474 0.044 Uiso 1 1 calc R . . . .
H10B H 0.0771 0.5239 0.3026 0.044 Uiso 1 1 calc R . . . .
C11 C 0.2920(4) 0.54288(12) 0.3914(3) 0.0344(8) Uani 1 1 d . . . . .
H11 H 0.3970 0.5331 0.3804 0.041 Uiso 1 1 calc R . . . .
C12 C 0.2657(4) 0.53609(12) 0.5401(3) 0.0356(9) Uani 1 1 d . . . . .
C13 C 0.3698(5) 0.62301(14) 0.3867(4) 0.0433(10) Uani 1 1 d . . . . .
C14 C 0.3317(4) 0.67083(13) 0.3370(4) 0.0416(9) Uani 1 1 d . . . . .
C15 C 0.2318(6) 0.68059(14) 0.2240(5) 0.0600(12) Uani 1 1 d . . . . .
H15 H 0.1860 0.6559 0.1705 0.072 Uiso 1 1 calc R . . . .
C16 C 0.1954(6) 0.72570(15) 0.1854(5) 0.0716(15) Uani 1 1 d . . . . .
H16 H 0.1238 0.7318 0.1077 0.086 Uiso 1 1 calc R . . . .
C17 C 0.2635(6) 0.76089(15) 0.2600(6) 0.0624(13) Uani 1 1 d . . . . .
C18 C 0.3678(6) 0.75271(16) 0.3708(6) 0.0732(15) Uani 1 1 d . . . . .
H18 H 0.4172 0.7776 0.4208 0.088 Uiso 1 1 calc R . . . .
C19 C 0.4003(5) 0.70743(16) 0.4090(5) 0.0622(13) Uani 1 1 d . . . . .
H19 H 0.4718 0.7015 0.4869 0.075 Uiso 1 1 calc R . . . .
Cl1 Cl 0.21926(17) 0.81788(4) 0.21250(19) 0.0954(6) Uani 1 1 d . . . . .
N1 N 0.2696(3) 0.49653(9) -0.1118(3) 0.0326(7) Uani 1 1 d . . . . .
H1 H 0.2859 0.4933 -0.1981 0.039 Uiso 1 1 calc R . . . .
N2 N 0.2703(3) 0.58990(10) 0.3444(3) 0.0353(7) Uani 1 1 d . . . . .
H2A H 0.1902 0.5970 0.2868 0.042 Uiso 1 1 calc R . . . .
O1 O 0.1119(3) 0.55636(9) -0.1743(2) 0.0428(7) Uani 1 1 d . . . . .
O2 O 0.3135(3) 0.50170(9) 0.6035(2) 0.0488(7) Uani 1 1 d . . . . .
O3 O 0.1867(3) 0.56819(9) 0.5900(2) 0.0464(7) Uani 1 1 d . . . . .
H3 H 0.1762 0.5619 0.6720 0.070 Uiso 1 1 calc GR . . . .
O4 O 0.4873(3) 0.61428(10) 0.4608(3) 0.0632(9) Uani 1 1 d . . . . .
C20 C -0.1108(6) 0.64603(17) -0.0861(6) 0.0768(15) Uani 1 1 d . . . . .
H20A H -0.1580 0.6202 -0.1398 0.115 Uiso 0.549(2) 1 calc R . P A 1
H20B H -0.0252 0.6575 -0.1296 0.115 Uiso 0.549(2) 1 calc R . P A 1
H20C H -0.0756 0.6355 0.0074 0.115 Uiso 0.549(2) 1 calc R . P A 1
H20D H -0.0758 0.6329 -0.1687 0.115 Uiso 0.451(2) 1 calc R . P A 2
H20E H -0.0335 0.6416 -0.0073 0.115 Uiso 0.451(2) 1 calc R . P A 2
H20F H -0.2038 0.6305 -0.0683 0.115 Uiso 0.451(2) 1 calc R . P A 2
C21 C -0.2710(8) 0.7022(2) -0.2618(5) 0.103(2) Uani 1 1 d . . . . .
H21A H -0.3092 0.6744 -0.3112 0.155 Uiso 0.549(2) 1 calc R . P A 1
H21B H -0.3440 0.7273 -0.2805 0.155 Uiso 0.549(2) 1 calc R . P A 1
H21C H -0.1750 0.7112 -0.2925 0.155 Uiso 0.549(2) 1 calc R . P A 1
H21D H -0.2234 0.6854 -0.3319 0.155 Uiso 0.451(2) 1 calc R . P A 2
H21E H -0.3622 0.6858 -0.2433 0.155 Uiso 0.451(2) 1 calc R . P A 2
H21F H -0.2976 0.7334 -0.2949 0.155 Uiso 0.451(2) 1 calc R . P A 2
O5 O -0.1922(9) 0.72650(18) -0.0103(5) 0.184(3) Uani 1 1 d . . . . .
S1A S -0.2428(3) 0.69048(10) -0.0792(3) 0.0751(6) Uani 0.549(2) 1 d . . P A 1
S1B S -0.1459(4) 0.70558(11) -0.1110(3) 0.0751(6) Uani 0.451(2) 1 d . . P A 2
C22 C -0.1507(7) 0.6068(2) 0.4842(5) 0.0891(18) Uani 1 1 d . . . . .
H22A H -0.2419 0.6141 0.5260 0.134 Uiso 0.882(2) 1 calc R . P B 1
H22B H -0.1234 0.5744 0.5024 0.134 Uiso 0.882(2) 1 calc R . P B 1
H22C H -0.0680 0.6268 0.5238 0.134 Uiso 0.882(2) 1 calc R . P B 1
H22D H -0.0718 0.5851 0.5206 0.134 Uiso 0.118(2) 1 calc R . P B 2
H22E H -0.1776 0.6264 0.5589 0.134 Uiso 0.118(2) 1 calc R . P B 2
H22F H -0.2397 0.5897 0.4440 0.134 Uiso 0.118(2) 1 calc R . P B 2
C23 C -0.2053(13) 0.6731(3) 0.3066(9) 0.199(6) Uani 1 1 d . . . . .
H23C H -0.2964 0.6813 0.3475 0.299 Uiso 0.882(2) 1 calc R . P B 1
H23A H -0.1176 0.6877 0.3593 0.299 Uiso 0.882(2) 1 calc R . P B 1
H23B H -0.2148 0.6841 0.2113 0.299 Uiso 0.882(2) 1 calc R . P B 1
H23F H -0.2271 0.6942 0.3799 0.299 Uiso 0.118(2) 1 calc R . P B 2
H23D H -0.1712 0.6910 0.2312 0.299 Uiso 0.118(2) 1 calc R . P B 2
H23E H -0.2967 0.6560 0.2724 0.299 Uiso 0.118(2) 1 calc R . P B 2
O6 O -0.0441(3) 0.60459(10) 0.2463(3) 0.0611(9) Uani 1 1 d . . . . .
S2A S -0.18352(16) 0.61581(5) 0.30927(15) 0.0658(5) Uani 0.882(2) 1 d . . P B 1
S2B S -0.0861(12) 0.6404(4) 0.3611(11) 0.0658(5) Uani 0.118(2) 1 d . . P B 2


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.435(4) . ?
C1 N1 1.350(4) . ?
C1 O1 1.262(4) . ?
C2 H2 0.9500 . ?
C2 C3 1.351(5) . ?
C3 C4 1.450(5) . ?
C3 C10 1.504(4) . ?
C4 C5 1.405(5) . ?
C4 C9 1.408(5) . ?
C5 H5 0.9500 . ?
C5 C6 1.365(5) . ?
C6 H6 0.9500 . ?
C6 C7 1.392(5) . ?
C7 H7 0.9500 . ?
C7 C8 1.383(5) . ?
C8 H8 0.9500 . ?
C8 C9 1.391(5) . ?
C9 N1 1.377(4) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C10 C11 1.543(5) . ?
C11 H11 1.0000 . ?
C11 C12 1.517(4) . ?
C11 N2 1.444(4) . ?
C12 O2 1.223(4) . ?
C12 O3 1.300(4) . ?
C13 C14 1.494(5) . ?
C13 N2 1.340(5) . ?
C13 O4 1.228(4) . ?
C14 C15 1.365(6) . ?
C14 C19 1.376(6) . ?
C15 H15 0.9500 . ?
C15 C16 1.388(6) . ?
C16 H16 0.9500 . ?
C16 C17 1.355(7) . ?
C17 C18 1.363(7) . ?
C17 Cl1 1.748(5) . ?
C18 H18 0.9500 . ?
C18 C19 1.385(6) . ?
C19 H19 0.9500 . ?
N1 H1 0.8800 . ?
N2 H2A 0.8800 . ?
O3 H3 0.8400 . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
C20 H20D 0.9800 . ?
C20 H20E 0.9800 . ?
C20 H20F 0.9800 . ?
C20 S1A 1.754(6) . ?
C20 S1B 1.765(6) . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
C21 H21D 0.9800 . ?
C21 H21E 0.9800 . ?
C21 H21F 0.9800 . ?
C21 S1A 1.809(6) . ?
C21 S1B 1.744(7) . ?
O5 S1A 1.294(6) . ?
O5 S1B 1.270(5) . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?
C22 H22D 0.9800 . ?
C22 H22E 0.9800 . ?
C22 H22F 0.9800 . ?
C22 S2A 1.724(5) . ?
C22 S2B 1.705(13) . ?
C23 H23C 0.9800 . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23F 0.9800 . ?
C23 H23D 0.9800 . ?
C23 H23E 0.9800 . ?
C23 S2A 1.672(7) . ?
C23 S2B 1.478(13) . ?
O6 S2A 1.494(3) . ?
O6 S2B 1.609(11) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 C1 C2 117.0(3) . . ?
O1 C1 C2 122.3(3) . . ?
O1 C1 N1 120.8(3) . . ?
C1 C2 H2 119.0 . . ?
C3 C2 C1 122.0(3) . . ?
C3 C2 H2 119.0 . . ?
C2 C3 C4 119.7(3) . . ?
C2 C3 C10 119.6(3) . . ?
C4 C3 C10 120.7(3) . . ?
C5 C4 C3 124.2(3) . . ?
C5 C4 C9 118.1(3) . . ?
C9 C4 C3 117.7(3) . . ?
C4 C5 H5 119.6 . . ?
C6 C5 C4 120.8(3) . . ?
C6 C5 H5 119.6 . . ?
C5 C6 H6 119.6 . . ?
C5 C6 C7 120.9(4) . . ?
C7 C6 H6 119.6 . . ?
C6 C7 H7 120.1 . . ?
C8 C7 C6 119.7(4) . . ?
C8 C7 H7 120.1 . . ?
C7 C8 H8 120.1 . . ?
C7 C8 C9 119.9(3) . . ?
C9 C8 H8 120.1 . . ?
C8 C9 C4 120.7(3) . . ?
N1 C9 C4 119.6(3) . . ?
N1 C9 C8 119.7(3) . . ?
C3 C10 H10A 108.8 . . ?
C3 C10 H10B 108.8 . . ?
C3 C10 C11 113.6(3) . . ?
H10A C10 H10B 107.7 . . ?
C11 C10 H10A 108.8 . . ?
C11 C10 H10B 108.8 . . ?
C10 C11 H11 109.0 . . ?
C12 C11 C10 107.0(3) . . ?
C12 C11 H11 109.0 . . ?
N2 C11 C10 109.4(3) . . ?
N2 C11 H11 109.0 . . ?
N2 C11 C12 113.5(3) . . ?
O2 C12 C11 120.5(3) . . ?
O2 C12 O3 124.3(3) . . ?
O3 C12 C11 115.1(3) . . ?
N2 C13 C14 116.5(3) . . ?
O4 C13 C14 121.9(4) . . ?
O4 C13 N2 121.6(4) . . ?
C15 C14 C13 123.9(4) . . ?
C15 C14 C19 117.6(4) . . ?
C19 C14 C13 118.5(4) . . ?
C14 C15 H15 119.2 . . ?
C14 C15 C16 121.6(4) . . ?
C16 C15 H15 119.2 . . ?
C15 C16 H16 120.5 . . ?
C17 C16 C15 119.1(5) . . ?
C17 C16 H16 120.5 . . ?
C16 C17 C18 121.2(4) . . ?
C16 C17 Cl1 119.6(4) . . ?
C18 C17 Cl1 119.2(4) . . ?
C17 C18 H18 120.6 . . ?
C17 C18 C19 118.8(4) . . ?
C19 C18 H18 120.6 . . ?
C14 C19 C18 121.7(4) . . ?
C14 C19 H19 119.2 . . ?
C18 C19 H19 119.2 . . ?
C1 N1 C9 124.0(3) . . ?
C1 N1 H1 118.0 . . ?
C9 N1 H1 118.0 . . ?
C11 N2 H2A 119.4 . . ?
C13 N2 C11 121.2(3) . . ?
C13 N2 H2A 119.4 . . ?
C12 O3 H3 109.5 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
H20D C20 H20E 109.5 . . ?
H20D C20 H20F 109.5 . . ?
H20E C20 H20F 109.5 . . ?
S1A C20 H20A 109.5 . . ?
S1A C20 H20B 109.5 . . ?
S1A C20 H20C 109.5 . . ?
S1B C20 H20D 109.5 . . ?
S1B C20 H20E 109.5 . . ?
S1B C20 H20F 109.5 . . ?
H21A C21 H21B 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
H21D C21 H21E 109.5 . . ?
H21D C21 H21F 109.5 . . ?
H21E C21 H21F 109.5 . . ?
S1A C21 H21A 109.5 . . ?
S1A C21 H21B 109.5 . . ?
S1A C21 H21C 109.5 . . ?
S1B C21 H21D 109.5 . . ?
S1B C21 H21E 109.5 . . ?
S1B C21 H21F 109.5 . . ?
C20 S1A C21 96.5(3) . . ?
O5 S1A C20 114.7(4) . . ?
O5 S1A C21 111.2(3) . . ?
C21 S1B C20 98.5(3) . . ?
O5 S1B C20 115.3(4) . . ?
O5 S1B C21 116.7(5) . . ?
H22A C22 H22B 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
H22D C22 H22E 109.5 . . ?
H22D C22 H22F 109.5 . . ?
H22E C22 H22F 109.5 . . ?
S2A C22 H22A 109.5 . . ?
S2A C22 H22B 109.5 . . ?
S2A C22 H22C 109.5 . . ?
S2B C22 H22D 109.5 . . ?
S2B C22 H22E 109.5 . . ?
S2B C22 H22F 109.5 . . ?
H23C C23 H23A 109.5 . . ?
H23C C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
H23F C23 H23D 109.5 . . ?
H23F C23 H23E 109.5 . . ?
H23D C23 H23E 109.5 . . ?
S2A C23 H23C 109.5 . . ?
S2A C23 H23A 109.5 . . ?
S2A C23 H23B 109.5 . . ?
S2B C23 H23F 109.5 . . ?
S2B C23 H23D 109.5 . . ?
S2B C23 H23E 109.5 . . ?
C23 S2A C22 99.9(4) . . ?
O6 S2A C22 109.2(2) . . ?
O6 S2A C23 108.1(3) . . ?
C23 S2B C22 109.3(7) . . ?
C23 S2B O6 112.4(8) . . ?
O6 S2B C22 104.8(7) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 0.5146(18)
2 0.4854(18)

