# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 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_imai_cf3bn_me075_twin1_hklf4
_database_code_depnum_ccdc_archive 'CCDC 2064229'
loop_
_audit_author_name
_audit_author_address
'Tetsuo Narumi'
;Shizuoka Univeristy
Japan
;
_audit_update_record             
;
2021-02-22 deposited with the CCDC.	2021-06-09 downloaded from the CCDC.
;
_audit_creation_date             2019-04-10
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C17 H21 Cl F3 N O4 S'
_chemical_formula_sum            'C17 H21 Cl F3 N O4 S'
_chemical_formula_weight         427.86
_chemical_melting_point          ?
_chemical_oxdiff_formula         C17H21ClF3NO4S
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'
F F 0.0171 0.0103 '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                   7.3770(8)
_cell_length_b                   11.8839(13)
_cell_length_c                   12.4930(17)
_cell_angle_alpha                90.570(10)
_cell_angle_beta                 106.868(11)
_cell_angle_gamma                100.186(9)
_cell_volume                     1029.4(2)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    2971
_cell_measurement_temperature    293.15
_cell_measurement_theta_max      32.5380
_cell_measurement_theta_min      2.9530
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.335
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.34968
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.47a (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.380
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             444
_exptl_crystal_size_max          0.561
_exptl_crystal_size_mid          0.235
_exptl_crystal_size_min          0.206
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1067
_diffrn_reflns_av_unetI/netI     0.0889
_diffrn_reflns_Laue_measured_fraction_full 0.983
_diffrn_reflns_Laue_measured_fraction_max 0.858
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            12539
_diffrn_reflns_point_group_measured_fraction_full 0.983
_diffrn_reflns_point_group_measured_fraction_max 0.858
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         32.946
_diffrn_reflns_theta_min         2.360
_diffrn_ambient_temperature      293.15
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 6.83
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 0.983
_diffrn_measured_fraction_theta_max 0.858
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -60.00 120.00   1.00   80.00    --   30.00  54.00   0.00  180
  2  ω    -60.00 120.00   1.00   80.00    --   30.00  54.00 120.00  180
  3  ω    -60.00 120.00   1.00   80.00    --   30.00  54.00 240.00  180
;
_diffrn_measurement_device       'fixed-chi diffractometer'
_diffrn_measurement_device_type  'Rigaku XtaLAB mini'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0013122000
_diffrn_orient_matrix_UB_12      -0.0087631000
_diffrn_orient_matrix_UB_13      -0.0559933000
_diffrn_orient_matrix_UB_21      0.0752546000
_diffrn_orient_matrix_UB_22      -0.0314917000
_diffrn_orient_matrix_UB_23      0.0188665000
_diffrn_orient_matrix_UB_31      -0.0692742000
_diffrn_orient_matrix_UB_32      -0.0512301000
_diffrn_orient_matrix_UB_33      -0.0066069000
_diffrn_radiation_monochromator  'curved graphite'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Sealed X-ray tube'
_diffrn_source_type              'Sealed X-ray tube'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4112
_reflns_number_total             6632
_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 1.171.40.47a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.47a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.47a (Rigaku OD, 2019)'
_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    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.391
_refine_diff_density_min         -0.483
_refine_diff_density_rms         0.093
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.020
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     277
_refine_ls_number_reflns         6632
_refine_ls_number_restraints     120
_refine_ls_R_factor_all          0.1380
_refine_ls_R_factor_gt           0.0922
_refine_ls_restrained_S_all      1.015
_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)+(0.1315P)²+0.7699P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2428
_refine_ls_wR_factor_ref         0.2750
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Uiso/Uaniso restraints and constraints
F1 \\sim F1A \\sim F2 \\sim F2A \\sim C17 \\sim F3 \\sim F3A: within 2A with
sigma of 0.04 and sigma for terminal atoms of 0.08
3. Rigid body (RIGU) restrains
 F2, F2A, F3, F3A, F1, F1A, C17
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
4. Others
 Sof(F3A)=Sof(F1A)=Sof(F2A)=1-FVAR(1)
 Sof(F1)=Sof(F3)=Sof(F2)=FVAR(1)
5.a Secondary CH2 refined with riding coordinates:
 C10(H10A,H10B)
5.b Aromatic/amide H refined with riding coordinates:
 C12(H12), C16(H16), C15(H15), C14(H14)
5.c Idealised Me refined as rotating group:
 C3(H3A,H3B,H3C), C9(H9A,H9B,H9C), C7(H7A,H7B,H7C), C6(H6A,H6B,H6C), C5(H5A,
 H5B,H5C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_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 0.63701(12) 0.75497(7) 0.21221(8) 0.0502(2) Uani 1 1 d . . . . .
Cl1 Cl 0.35790(15) 0.69783(9) -0.06760(7) 0.0577(3) Uani 1 1 d . . . . .
O4 O -0.0156(4) 0.7556(2) -0.0725(2) 0.0562(6) Uani 1 1 d . . . . .
O3 O 0.1361(5) 0.8803(2) 0.0744(3) 0.0672(8) Uani 1 1 d . . . . .
O1 O 0.6725(5) 0.6868(3) 0.3070(3) 0.0754(9) Uani 1 1 d . . . . .
O2 O 0.7235(4) 0.7378(3) 0.1267(3) 0.0719(8) Uani 1 1 d . . . . .
N1 N 0.3967(4) 0.7354(2) 0.1628(2) 0.0418(5) Uani 1 1 d . . . . .
C8 C 0.1245(5) 0.7951(3) 0.0200(3) 0.0428(6) Uani 1 1 d . . . . .
C2 C 0.2653(4) 0.6225(2) 0.1276(2) 0.0394(6) Uani 1 1 d . . . . .
C10 C 0.0975(5) 0.6009(3) 0.1776(3) 0.0472(7) Uani 1 1 d . . . . .
H10A H 0.042826 0.669767 0.174383 0.057 Uiso 1 1 calc R . . . .
H10B H -0.001879 0.540387 0.132196 0.057 Uiso 1 1 calc R . . . .
F1 F 0.5081(9) 0.7868(5) 0.5817(5) 0.114(2) Uani 0.867(10) 1 d . U P A 1
C11 C 0.1541(4) 0.5676(3) 0.2974(3) 0.0413(6) Uani 1 1 d . . . . .
C1 C 0.2725(5) 0.7175(2) 0.0484(2) 0.0402(6) Uani 1 1 d . . . . .
C3 C 0.3497(6) 0.5180(3) 0.1126(3) 0.0528(8) Uani 1 1 d . . . . .
H3A H 0.457347 0.540135 0.083870 0.079 Uiso 1 1 calc GR . . . .
H3B H 0.253165 0.462305 0.060861 0.079 Uiso 1 1 calc GR . . . .
H3C H 0.392125 0.485588 0.183597 0.079 Uiso 1 1 calc GR . . . .
C12 C 0.2269(5) 0.6522(3) 0.3855(3) 0.0485(7) Uani 1 1 d . . . . .
H12 H 0.239737 0.729104 0.370013 0.058 Uiso 1 1 calc R . . . .
C16 C 0.1372(6) 0.4532(3) 0.3243(3) 0.0552(8) Uani 1 1 d . . . . .
H16 H 0.088943 0.395411 0.267128 0.066 Uiso 1 1 calc R . . . .
F3 F 0.2209(9) 0.7785(5) 0.5875(6) 0.127(3) Uani 0.867(10) 1 d . U P A 1
C9 C -0.1620(6) 0.8240(4) -0.1104(4) 0.0681(11) Uani 1 1 d . . . . .
H9A H -0.254424 0.788711 -0.178604 0.102 Uiso 1 1 calc GR . . . .
H9B H -0.103567 0.899261 -0.123622 0.102 Uiso 1 1 calc GR . . . .
H9C H -0.225814 0.829588 -0.054113 0.102 Uiso 1 1 calc GR . . . .
C13 C 0.2804(6) 0.6224(3) 0.4960(3) 0.0533(8) Uani 1 1 d . . . . .
F2 F 0.4032(13) 0.6761(5) 0.6883(3) 0.136(3) Uani 0.867(10) 1 d . U P A 1
C15 C 0.1914(7) 0.4247(3) 0.4348(4) 0.0616(9) Uani 1 1 d . . . . .
H15 H 0.179452 0.347920 0.450779 0.074 Uiso 1 1 calc R . . . .
C4 C 0.7000(7) 0.9051(3) 0.2595(4) 0.0643(10) Uani 1 1 d . . . . .
C14 C 0.2630(7) 0.5087(4) 0.5219(3) 0.0610(9) Uani 1 1 d . . . . .
H14 H 0.298507 0.489248 0.596058 0.073 Uiso 1 1 calc R . . . .
C7 C 0.6486(9) 0.9768(4) 0.1597(5) 0.0902(17) Uani 1 1 d . . . . .
H7A H 0.698510 0.952044 0.102409 0.135 Uiso 1 1 calc GR . . . .
H7B H 0.703660 1.055897 0.182296 0.135 Uiso 1 1 calc GR . . . .
H7C H 0.510871 0.967955 0.131003 0.135 Uiso 1 1 calc GR . . . .
C17 C 0.3521(9) 0.7148(5) 0.5867(4) 0.0762(12) Uani 1 1 d . U . . .
C6 C 0.5952(11) 0.9237(5) 0.3449(6) 0.102(2) Uani 1 1 d . . . . .
H6A H 0.459641 0.915727 0.307608 0.153 Uiso 1 1 calc GR . . . .
H6B H 0.644118 0.999236 0.380994 0.153 Uiso 1 1 calc GR . . . .
H6C H 0.615849 0.867896 0.400071 0.153 Uiso 1 1 calc GR . . . .
C5 C 0.9221(9) 0.9271(5) 0.3132(6) 0.101(2) Uani 1 1 d . . . . .
H5A H 0.953271 0.883257 0.378005 0.152 Uiso 1 1 calc GR . . . .
H5B H 0.968450 1.007090 0.335110 0.152 Uiso 1 1 calc GR . . . .
H5C H 0.981872 0.904415 0.259808 0.152 Uiso 1 1 calc GR . . . .
F3A F 0.346(8) 0.827(2) 0.537(2) 0.115(10) Uani 0.133(10) 1 d . U P A 2
F1A F 0.523(6) 0.733(4) 0.635(3) 0.126(10) Uani 0.133(10) 1 d . U P A 2
F2A F 0.273(6) 0.732(4) 0.652(3) 0.114(9) Uani 0.133(10) 1 d . U P A 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
S1 O1 1.429(3) . ?
S1 O2 1.423(3) . ?
S1 N1 1.672(3) . ?
S1 C4 1.810(4) . ?
Cl1 C1 1.768(3) . ?
O4 C8 1.323(4) . ?
O4 C9 1.440(5) . ?
O3 C8 1.190(4) . ?
N1 C2 1.487(4) . ?
N1 C1 1.446(4) . ?
C8 C1 1.519(4) . ?
C2 C10 1.526(4) . ?
C2 C1 1.513(4) . ?
C2 C3 1.517(4) . ?
C10 C11 1.510(4) . ?
F1 C17 1.325(7) . ?
C11 C12 1.398(5) . ?
C11 C16 1.396(5) . ?
C12 C13 1.389(5) . ?
C16 C15 1.385(5) . ?
F3 C17 1.332(8) . ?
C13 C14 1.385(6) . ?
C13 C17 1.479(6) . ?
F2 C17 1.328(7) . ?
C15 C14 1.385(6) . ?
C4 C7 1.511(6) . ?
C4 C6 1.523(7) . ?
C4 C5 1.552(7) . ?
C17 F3A 1.48(3) . ?
C17 F1A 1.21(4) . ?
C17 F2A 1.17(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 S1 N1 104.46(17) . . ?
O1 S1 C4 109.5(2) . . ?
O2 S1 O1 118.7(2) . . ?
O2 S1 N1 112.23(17) . . ?
O2 S1 C4 108.8(2) . . ?
N1 S1 C4 101.95(18) . . ?
C8 O4 C9 116.3(3) . . ?
C2 N1 S1 125.2(2) . . ?
C1 N1 S1 129.8(2) . . ?
C1 N1 C2 62.08(19) . . ?
O4 C8 C1 111.0(3) . . ?
O3 C8 O4 125.3(3) . . ?
O3 C8 C1 123.7(3) . . ?
N1 C2 C10 114.9(3) . . ?
N1 C2 C1 57.63(18) . . ?
N1 C2 C3 119.1(3) . . ?
C1 C2 C10 118.4(3) . . ?
C1 C2 C3 119.3(3) . . ?
C3 C2 C10 115.2(3) . . ?
C11 C10 C2 113.5(3) . . ?
C12 C11 C10 120.2(3) . . ?
C16 C11 C10 121.9(3) . . ?
C16 C11 C12 117.9(3) . . ?
N1 C1 Cl1 123.2(2) . . ?
N1 C1 C8 113.7(2) . . ?
N1 C1 C2 60.29(19) . . ?
C8 C1 Cl1 110.1(2) . . ?
C2 C1 Cl1 119.0(2) . . ?
C2 C1 C8 122.9(3) . . ?
C13 C12 C11 120.6(3) . . ?
C15 C16 C11 120.9(3) . . ?
C12 C13 C17 118.7(4) . . ?
C14 C13 C12 121.1(3) . . ?
C14 C13 C17 120.2(4) . . ?
C16 C15 C14 121.0(3) . . ?
C7 C4 S1 109.4(3) . . ?
C7 C4 C6 112.7(5) . . ?
C7 C4 C5 110.0(4) . . ?
C6 C4 S1 108.2(3) . . ?
C6 C4 C5 111.9(5) . . ?
C5 C4 S1 104.4(4) . . ?
C13 C14 C15 118.5(3) . . ?
F1 C17 F3 106.3(6) . . ?
F1 C17 C13 114.0(4) . . ?
F1 C17 F2 104.2(6) . . ?
F3 C17 C13 112.6(5) . . ?
C13 C17 F3A 109.4(10) . . ?
F2 C17 F3 105.9(6) . . ?
F2 C17 C13 113.2(5) . . ?
F1A C17 C13 117(2) . . ?
F1A C17 F3A 97(3) . . ?
F2A C17 C13 124.9(18) . . ?
F2A C17 F3A 96(3) . . ?
F2A C17 F1A 108(3) . . ?

_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 2.512
_oxdiff_exptl_absorpt_empirical_full_min 0.475
_oxdiff_twin_integration_method  simultaneous
_oxdiff_twin_items               3
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 0.4210 1767 12177 ref 1.0000 0.0000 0.0000 0.0000 1.0000 0.0000 0.0000 0.0000
1.0000
2 0.2616 0 11505 nmt 1.0015 0.0016 -0.0021 -0.5751 -1.0001 -0.0123 -0.9834
0.0129 -0.9969
3 0.3174 0 11563 nmt 1.0027 0.0033 -0.0018 -0.5552 -1.0006 0.0146 -0.9909
-0.0112 -0.9994

_twin_special_details            
;
Component 2 rotated by 179.2097° 
 around [0.87 -0.25 -0.43] (reciprocal) or [1.00 0.00 -0.00] (direct)
Component 3 rotated by -179.4368° 
 around [0.87 -0.24 -0.43] (reciprocal) or [1.00 0.00 -0.00] (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_kodama_20210222
_database_code_depnum_ccdc_archive 'CCDC 2065548'
loop_
_audit_author_name
_audit_author_address
'Tetsuo Narumi'
;Shizuoka Univeristy
Japan
;
_audit_update_record             
;
2021-03-01 deposited with the CCDC.	2021-06-09 downloaded from the CCDC.
;
_audit_creation_date             2021-02-26
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6257)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C15 H24 Cl N O4 S'
_chemical_formula_sum            'C15 H24 Cl N O4 S'
_chemical_formula_weight         349.86
_chemical_melting_point          ?
_chemical_oxdiff_formula         C15H24ClNO4S
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      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                   7.0093(11)
_cell_length_b                   8.9932(9)
_cell_length_c                   14.7723(15)
_cell_angle_alpha                93.204(8)
_cell_angle_beta                 99.536(10)
_cell_angle_gamma                96.869(10)
_cell_volume                     909.0(2)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    2618
_cell_measurement_temperature    293
_cell_measurement_theta_max      32.4880
_cell_measurement_theta_min      2.3730
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.340
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.59579
_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            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.278
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             372
_exptl_crystal_size_max          0.261
_exptl_crystal_size_mid          0.233
_exptl_crystal_size_min          0.085
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0350
_diffrn_reflns_av_unetI/netI     0.0456
_diffrn_reflns_Laue_measured_fraction_full 0.989
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            7608
_diffrn_reflns_point_group_measured_fraction_full 0.989
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_theta_full        25.123
_diffrn_reflns_theta_max         25.123
_diffrn_reflns_theta_min         2.288
_diffrn_ambient_temperature      293
_diffrn_detector                 'Rigaku Mercury area detector'
_diffrn_detector_area_resol_mean 6.83
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -60.00 120.00   1.00  120.00    --   30.00  54.00   0.00  180
  2  ω    -60.00 120.00   1.00  120.00    --   30.00  54.00 120.00  180
  3  ω    -60.00 120.00   1.00  120.00    --   30.00  54.00 240.00  180
;
_diffrn_measurement_device       'fixed-chi diffractometer'
_diffrn_measurement_device_type  'Rigaku XtaLAB mini'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0184560000
_diffrn_orient_matrix_UB_12      0.0586344000
_diffrn_orient_matrix_UB_13      0.0357145000
_diffrn_orient_matrix_UB_21      0.0182758000
_diffrn_orient_matrix_UB_22      -0.0530817000
_diffrn_orient_matrix_UB_23      0.0330839000
_diffrn_orient_matrix_UB_31      0.1001911000
_diffrn_orient_matrix_UB_32      0.0096538000
_diffrn_orient_matrix_UB_33      -0.0038417000
_diffrn_radiation_monochromator  'curved graphite'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Sealed X-ray tube'
_diffrn_source_type              'Sealed X-ray tube'
_diffrn_special_details          ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2464
_reflns_number_total             3211
_reflns_odcompleteness_completeness 89.08
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     33.13
_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 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'olex2.solve 1.3 (Bourhis et al., 2015)'
_refine_diff_density_max         0.249
_refine_diff_density_min         -0.239
_refine_diff_density_rms         0.043
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.132
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     222
_refine_ls_number_reflns         3211
_refine_ls_number_restraints     72
_refine_ls_R_factor_all          0.0764
_refine_ls_R_factor_gt           0.0568
_refine_ls_restrained_S_all      1.123
_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)+(0.0398P)²+0.7456P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1324
_refine_ls_wR_factor_ref         0.1423
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All C(H,H,H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Uiso/Uaniso restraints and constraints
C6 \\sim C12 \\sim C13A \\sim C13 \\sim C14A \\sim C14 \\sim C15: within 2A
with sigma of 0.04 and sigma for terminal atoms of 0.08 within 2A
3. Others
 Sof(H12C)=Sof(H12D)=Sof(H15C)=Sof(H15D)=Sof(C14A)=Sof(H14C)=Sof(H14D)=
 Sof(C13A)=Sof(H13C)=Sof(H13D)=1-FVAR(1)
 Sof(H12A)=Sof(H12B)=Sof(H15A)=Sof(H15B)=Sof(C13)=Sof(H13A)=Sof(H13B)=Sof(C14)=
 Sof(H14A)=Sof(H14B)=FVAR(1)
4.a Secondary CH2 refined with riding coordinates:
 C12(H12A,H12B), C12(H12C,H12D), C10(H10A,H10B), C15(H15A,H15B), C15(H15C,
 H15D), C13(H13A,H13B), C14(H14A,H14B), C14A(H14C,H14D), C13A(H13C,H13D)
4.b Aromatic/amide H refined with riding coordinates:
 C7(H7), C8(H8)
4.c Idealised Me refined as rotating group:
 C11(H11A,H11B,H11C), C4(H4A,H4B,H4C), C2(H2A,H2B,H2C), C3(H3A,H3B,H3C)
;
_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
S1 S 0.08451(13) 0.61345(9) 0.18669(6) 0.0520(3) Uani 1 1 d . . . . .
Cl1 Cl -0.04423(13) 0.98704(10) 0.33350(6) 0.0627(3) Uani 1 1 d . . . . .
O3 O 0.5301(3) 0.7317(3) 0.51126(15) 0.0591(6) Uani 1 1 d . . . . .
N1 N 0.0655(4) 0.7926(3) 0.21387(16) 0.0456(6) Uani 1 1 d . . . . .
O2 O 0.1897(4) 0.5466(3) 0.26090(18) 0.0765(8) Uani 1 1 d . . . . .
O1 O 0.1546(4) 0.6122(3) 0.10164(18) 0.0756(8) Uani 1 1 d . . . . .
O4 O 0.3750(5) 0.8124(4) 0.62055(17) 0.0841(9) Uani 1 1 d . . . . .
C7 C 0.2630(4) 0.8278(3) 0.3784(2) 0.0444(7) Uani 1 1 d . . . . .
H7 H 0.352392 0.765993 0.363579 0.053 Uiso 1 1 calc R U . . .
C6 C 0.2169(5) 0.9217(4) 0.2155(2) 0.0493(8) Uani 1 1 d . U . . .
C5 C 0.1359(5) 0.8834(4) 0.3004(2) 0.0462(7) Uani 1 1 d . . . . .
C12 C 0.4265(5) 0.9058(4) 0.2067(2) 0.0582(9) Uani 1 1 d . U . . .
H12A H 0.449708 0.801640 0.206998 0.070 Uiso 0.59(2) 1 calc R U P A 1
H12B H 0.517870 0.964673 0.255931 0.070 Uiso 0.59(2) 1 calc R U P A 1
H12C H 0.511325 0.930773 0.265815 0.070 Uiso 0.41(2) 1 calc R U P A 2
H12D H 0.436839 0.803223 0.186095 0.070 Uiso 0.41(2) 1 calc R U P A 2
C9 C 0.3917(5) 0.8002(4) 0.5412(2) 0.0533(8) Uani 1 1 d . . . . .
C8 C 0.2616(5) 0.8573(4) 0.4662(2) 0.0512(8) Uani 1 1 d . . . . .
H8 H 0.172360 0.918373 0.482124 0.061 Uiso 1 1 calc R U . . .
C10 C 0.6620(6) 0.6674(5) 0.5794(2) 0.0659(10) Uani 1 1 d . . . . .
H10A H 0.592805 0.583257 0.603966 0.079 Uiso 1 1 calc R U . . .
H10B H 0.717793 0.741924 0.629796 0.079 Uiso 1 1 calc R U . . .
C1 C -0.1681(5) 0.5333(4) 0.1679(2) 0.0578(9) Uani 1 1 d . . . . .
C15 C 0.1554(6) 1.0483(4) 0.1576(3) 0.0702(11) Uani 1 1 d . U . . .
H15A H 0.052019 1.009775 0.106734 0.084 Uiso 0.59(2) 1 calc R U P A 1
H15B H 0.108759 1.123884 0.194755 0.084 Uiso 0.59(2) 1 calc R U P A 1
H15C H 0.187872 1.145203 0.192546 0.084 Uiso 0.41(2) 1 calc R U P A 2
H15D H 0.016944 1.032143 0.132675 0.084 Uiso 0.41(2) 1 calc R U P A 2
C11 C 0.8190(6) 0.6161(5) 0.5333(3) 0.0812(12) Uani 1 1 d . . . . .
H11A H 0.762810 0.539361 0.485301 0.122 Uiso 1 1 calc R U . . .
H11B H 0.912151 0.576524 0.577560 0.122 Uiso 1 1 calc R U . . .
H11C H 0.883154 0.699519 0.507194 0.122 Uiso 1 1 calc R U . . .
C4 C -0.2798(6) 0.6071(5) 0.0894(3) 0.0779(12) Uani 1 1 d . . . . .
H4A H -0.269482 0.713112 0.105205 0.117 Uiso 1 1 calc R U . . .
H4B H -0.414614 0.564535 0.078780 0.117 Uiso 1 1 calc R U . . .
H4C H -0.225942 0.590299 0.034620 0.117 Uiso 1 1 calc R U . . .
C2 C -0.2471(6) 0.5572(5) 0.2570(3) 0.0791(12) Uani 1 1 d . . . . .
H2A H -0.177377 0.505301 0.304197 0.119 Uiso 1 1 calc R U . . .
H2B H -0.383282 0.518804 0.247186 0.119 Uiso 1 1 calc R U . . .
H2C H -0.230282 0.662619 0.275632 0.119 Uiso 1 1 calc R U . . .
C3 C -0.1691(8) 0.3659(5) 0.1412(4) 0.0994(16) Uani 1 1 d . . . . .
H3A H -0.099618 0.355019 0.090889 0.149 Uiso 1 1 calc R U . . .
H3B H -0.301261 0.318722 0.122967 0.149 Uiso 1 1 calc R U . . .
H3C H -0.106888 0.319162 0.192995 0.149 Uiso 1 1 calc R U . . .
C13 C 0.443(3) 0.967(2) 0.1129(14) 0.081(4) Uani 0.59(2) 1 d . U P A 1
H13A H 0.376033 0.897150 0.062020 0.097 Uiso 0.59(2) 1 calc R U P A 1
H13B H 0.577139 0.994779 0.105908 0.097 Uiso 0.59(2) 1 calc R U P A 1
C14 C 0.331(2) 1.1131(18) 0.1231(14) 0.106(4) Uani 0.59(2) 1 d . U P A 1
H14A H 0.409169 1.190319 0.166695 0.127 Uiso 0.59(2) 1 calc R U P A 1
H14B H 0.296662 1.154713 0.064274 0.127 Uiso 0.59(2) 1 calc R U P A 1
C14A C 0.280(3) 1.034(3) 0.0817(12) 0.091(5) Uani 0.41(2) 1 d . U P A 2
H14C H 0.290389 1.125176 0.049403 0.109 Uiso 0.41(2) 1 calc R U P A 2
H14D H 0.226082 0.949504 0.037622 0.109 Uiso 0.41(2) 1 calc R U P A 2
C13A C 0.484(5) 1.009(4) 0.139(2) 0.092(6) Uani 0.41(2) 1 d . U P A 2
H13C H 0.564147 0.964109 0.100355 0.110 Uiso 0.41(2) 1 calc R U P A 2
H13D H 0.555232 1.102820 0.169483 0.110 Uiso 0.41(2) 1 calc R U P A 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
S1 N1 1.665(3) . ?
S1 O2 1.421(2) . ?
S1 O1 1.423(3) . ?
S1 C1 1.800(4) . ?
Cl1 C5 1.771(3) . ?
O3 C9 1.331(4) . ?
O3 C10 1.445(4) . ?
N1 C6 1.472(4) . ?
N1 C5 1.456(4) . ?
O4 C9 1.197(4) . ?
C7 H7 0.9300 . ?
C7 C5 1.484(4) . ?
C7 C8 1.311(4) . ?
C6 C5 1.501(4) . ?
C6 C12 1.519(5) . ?
C6 C15 1.522(4) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C12 H12C 0.9700 . ?
C12 H12D 0.9700 . ?
C12 C13 1.54(2) . ?
C12 C13A 1.47(4) . ?
C9 C8 1.471(5) . ?
C8 H8 0.9300 . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C10 C11 1.491(5) . ?
C1 C4 1.519(5) . ?
C1 C2 1.524(5) . ?
C1 C3 1.534(5) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C15 H15C 0.9700 . ?
C15 H15D 0.9700 . ?
C15 C14 1.477(12) . ?
C15 C14A 1.539(15) . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C4 H4A 0.9600 . ?
C4 H4B 0.9600 . ?
C4 H4C 0.9600 . ?
C2 H2A 0.9600 . ?
C2 H2B 0.9600 . ?
C2 H2C 0.9600 . ?
C3 H3A 0.9600 . ?
C3 H3B 0.9600 . ?
C3 H3C 0.9600 . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C13 C14 1.62(3) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C14A H14C 0.9700 . ?
C14A H14D 0.9700 . ?
C14A C13A 1.59(4) . ?
C13A H13C 0.9700 . ?
C13A H13D 0.9700 . ?

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 S1 C1 100.65(15) . . ?
O2 S1 N1 112.06(14) . . ?
O2 S1 O1 118.01(17) . . ?
O2 S1 C1 109.42(18) . . ?
O1 S1 N1 105.41(15) . . ?
O1 S1 C1 109.84(17) . . ?
C9 O3 C10 116.9(3) . . ?
C6 N1 S1 126.4(2) . . ?
C5 N1 S1 129.5(2) . . ?
C5 N1 C6 61.7(2) . . ?
C5 C7 H7 116.8 . . ?
C8 C7 H7 116.8 . . ?
C8 C7 C5 126.4(3) . . ?
N1 C6 C5 58.6(2) . . ?
N1 C6 C12 123.4(3) . . ?
N1 C6 C15 115.5(3) . . ?
C5 C6 C12 122.0(3) . . ?
C5 C6 C15 123.1(3) . . ?
C12 C6 C15 107.4(3) . . ?
N1 C5 Cl1 112.1(2) . . ?
N1 C5 C7 122.1(3) . . ?
N1 C5 C6 59.7(2) . . ?
C7 C5 Cl1 114.3(2) . . ?
C7 C5 C6 119.5(3) . . ?
C6 C5 Cl1 118.6(2) . . ?
C6 C12 H12A 111.3 . . ?
C6 C12 H12B 111.3 . . ?
C6 C12 H12C 110.1 . . ?
C6 C12 H12D 110.1 . . ?
C6 C12 C13 102.4(9) . . ?
H12A C12 H12B 109.2 . . ?
H12C C12 H12D 108.4 . . ?
C13 C12 H12A 111.3 . . ?
C13 C12 H12B 111.3 . . ?
C13A C12 C6 107.9(15) . . ?
C13A C12 H12C 110.1 . . ?
C13A C12 H12D 110.1 . . ?
O3 C9 C8 112.6(3) . . ?
O4 C9 O3 123.3(3) . . ?
O4 C9 C8 124.1(3) . . ?
C7 C8 C9 124.4(3) . . ?
C7 C8 H8 117.8 . . ?
C9 C8 H8 117.8 . . ?
O3 C10 H10A 110.2 . . ?
O3 C10 H10B 110.2 . . ?
O3 C10 C11 107.6(3) . . ?
H10A C10 H10B 108.5 . . ?
C11 C10 H10A 110.2 . . ?
C11 C10 H10B 110.2 . . ?
C4 C1 S1 109.0(3) . . ?
C4 C1 C2 111.7(3) . . ?
C4 C1 C3 110.4(3) . . ?
C2 C1 S1 108.6(3) . . ?
C2 C1 C3 111.5(4) . . ?
C3 C1 S1 105.4(3) . . ?
C6 C15 H15A 110.5 . . ?
C6 C15 H15B 110.5 . . ?
C6 C15 H15C 111.7 . . ?
C6 C15 H15D 111.7 . . ?
C6 C15 C14A 100.4(6) . . ?
H15A C15 H15B 108.7 . . ?
H15C C15 H15D 109.5 . . ?
C14 C15 C6 106.3(5) . . ?
C14 C15 H15A 110.5 . . ?
C14 C15 H15B 110.5 . . ?
C14A C15 H15C 111.7 . . ?
C14A C15 H15D 111.7 . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C1 C4 H4A 109.5 . . ?
C1 C4 H4B 109.5 . . ?
C1 C4 H4C 109.5 . . ?
H4A C4 H4B 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
C1 C2 H2A 109.5 . . ?
C1 C2 H2B 109.5 . . ?
C1 C2 H2C 109.5 . . ?
H2A C2 H2B 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?
C1 C3 H3A 109.5 . . ?
C1 C3 H3B 109.5 . . ?
C1 C3 H3C 109.5 . . ?
H3A C3 H3B 109.5 . . ?
H3A C3 H3C 109.5 . . ?
H3B C3 H3C 109.5 . . ?
C12 C13 H13A 112.0 . . ?
C12 C13 H13B 112.0 . . ?
C12 C13 C14 98.7(14) . . ?
H13A C13 H13B 109.7 . . ?
C14 C13 H13A 112.0 . . ?
C14 C13 H13B 112.0 . . ?
C15 C14 C13 101.6(12) . . ?
C15 C14 H14A 111.5 . . ?
C15 C14 H14B 111.5 . . ?
C13 C14 H14A 111.5 . . ?
C13 C14 H14B 111.5 . . ?
H14A C14 H14B 109.3 . . ?
C15 C14A H14C 111.4 . . ?
C15 C14A H14D 111.4 . . ?
C15 C14A C13A 101.9(17) . . ?
H14C C14A H14D 109.3 . . ?
C13A C14A H14C 111.4 . . ?
C13A C14A H14D 111.4 . . ?
C12 C13A C14A 102(2) . . ?
C12 C13A H13C 111.3 . . ?
C12 C13A H13D 111.3 . . ?
C14A C13A H13C 111.3 . . ?
C14A C13A H13D 111.3 . . ?
H13C C13A H13D 109.2 . . ?

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 N1 C6 C5 -120.0(3) . . . . ?
S1 N1 C6 C12 -10.1(4) . . . . ?
S1 N1 C6 C15 125.3(3) . . . . ?
S1 N1 C5 Cl1 -133.4(2) . . . . ?
S1 N1 C5 C7 7.6(4) . . . . ?
S1 N1 C5 C6 115.4(3) . . . . ?
O3 C9 C8 C7 8.6(5) . . . . ?
N1 S1 C1 C4 61.0(3) . . . . ?
N1 S1 C1 C2 -60.9(3) . . . . ?
N1 S1 C1 C3 179.5(3) . . . . ?
N1 C6 C5 Cl1 -100.2(3) . . . . ?
N1 C6 C5 C7 112.1(3) . . . . ?
N1 C6 C12 C13 112.5(8) . . . . ?
N1 C6 C12 C13A 133.3(13) . . . . ?
N1 C6 C15 C14 -146.9(10) . . . . ?
N1 C6 C15 C14A -111.5(11) . . . . ?
O2 S1 N1 C6 79.5(3) . . . . ?
O2 S1 N1 C5 -1.5(3) . . . . ?
O2 S1 C1 C4 179.2(2) . . . . ?
O2 S1 C1 C2 57.3(3) . . . . ?
O2 S1 C1 C3 -62.3(3) . . . . ?
O1 S1 N1 C6 -50.1(3) . . . . ?
O1 S1 N1 C5 -131.1(3) . . . . ?
O1 S1 C1 C4 -49.8(3) . . . . ?
O1 S1 C1 C2 -171.7(2) . . . . ?
O1 S1 C1 C3 68.7(3) . . . . ?
O4 C9 C8 C7 -170.8(4) . . . . ?
C6 N1 C5 Cl1 111.2(3) . . . . ?
C6 N1 C5 C7 -107.8(3) . . . . ?
C6 C12 C13 C14 43.4(13) . . . . ?
C6 C12 C13A C14A -22(2) . . . . ?
C6 C15 C14 C13 31.9(16) . . . . ?
C6 C15 C14A C13A -43(2) . . . . ?
C5 N1 C6 C12 110.0(3) . . . . ?
C5 N1 C6 C15 -114.7(3) . . . . ?
C5 C7 C8 C9 -179.6(3) . . . . ?
C5 C6 C12 C13 -176.3(8) . . . . ?
C5 C6 C12 C13A -155.6(12) . . . . ?
C5 C6 C15 C14 145.2(10) . . . . ?
C5 C6 C15 C14A -179.3(11) . . . . ?
C12 C6 C5 Cl1 147.5(3) . . . . ?
C12 C6 C5 N1 -112.3(3) . . . . ?
C12 C6 C5 C7 -0.2(5) . . . . ?
C12 C6 C15 C14 -4.9(10) . . . . ?
C12 C6 C15 C14A 30.6(11) . . . . ?
C12 C13 C14 C15 -47.0(17) . . . . ?
C9 O3 C10 C11 -172.4(3) . . . . ?
C8 C7 C5 Cl1 -5.1(4) . . . . ?
C8 C7 C5 N1 -145.3(3) . . . . ?
C8 C7 C5 C6 143.9(3) . . . . ?
C10 O3 C9 O4 1.3(5) . . . . ?
C10 O3 C9 C8 -178.1(3) . . . . ?
C1 S1 N1 C6 -164.3(2) . . . . ?
C1 S1 N1 C5 114.7(3) . . . . ?
C15 C6 C5 Cl1 1.6(4) . . . . ?
C15 C6 C5 N1 101.8(4) . . . . ?
C15 C6 C5 C7 -146.1(3) . . . . ?
C15 C6 C12 C13 -25.8(8) . . . . ?
C15 C6 C12 C13A -5.0(13) . . . . ?
C15 C14A C13A C12 41(3) . . . . ?

_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
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.360
_oxdiff_exptl_absorpt_empirical_full_min 0.762
####################################################################### 
# 
# 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_sim_down
_database_code_depnum_ccdc_archive 'CCDC 2064228'
loop_
_audit_author_name
_audit_author_address
'Tetsuo Narumi'
;Shizuoka Univeristy
Japan
;
_audit_update_record             
;
2021-02-22 deposited with the CCDC.	2021-06-09 downloaded from the CCDC.
;
_audit_creation_date             2019-02-13
_audit_creation_method           
;
Olex2 1.2
(compiled May 18 2018 14:05:52 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C14 H18 Br Cl2 N O4 S'
_chemical_formula_sum            'C14 H18 Br Cl2 N O4 S'
_chemical_formula_weight         447.16
_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'
Br Br -0.2901 2.4595 '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                   12.396(4)
_cell_length_b                   14.044(4)
_cell_length_c                   11.920(3)
_cell_angle_alpha                90
_cell_angle_beta                 118.17(4)
_cell_angle_gamma                90
_cell_volume                     1829.3(11)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2113
_cell_measurement_temperature    293.15
_cell_measurement_theta_max      30.3190
_cell_measurement_theta_min      2.3260
_shelx_estimated_absorpt_T_max   0.856
_shelx_estimated_absorpt_T_min   0.740
_exptl_absorpt_coefficient_mu    2.670
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.73927
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.35a (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_density_diffrn    1.624
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             904
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.06
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1016
_diffrn_reflns_av_unetI/netI     0.0773
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            15794
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.348
_diffrn_reflns_theta_min         2.362
_diffrn_ambient_temperature      293.15
_diffrn_detector_area_resol_mean 6.83
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -60.00 120.00   1.00   70.00    --   30.00  54.00   0.00  180
  2  ω    -60.00 120.00   1.00   70.00    --   30.00  54.00 120.00  180
  3  ω    -60.00 120.00   1.00   70.00    --   30.00  54.00 240.00  180
;
_diffrn_measurement_device       'fixed-chi diffractometer'
_diffrn_measurement_device_type  'XtaLAB Mini'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1768
_reflns_number_total             3349
_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 1.171.40.35a (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.40.35a (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.40.35a (Rigaku OD, 2018)'
_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    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.439
_refine_diff_density_min         -0.507
_refine_diff_density_rms         0.069
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     234
_refine_ls_number_reflns         3349
_refine_ls_number_restraints     18
_refine_ls_R_factor_all          0.1256
_refine_ls_R_factor_gt           0.0527
_refine_ls_restrained_S_all      1.023
_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)+(0.0358P)²+0.6943P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0960
_refine_ls_wR_factor_ref         0.1205
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.5 times of:
  All C(H,H,H) groups, H1 of C6A
 At 1.2 times of:
  H2 of C2, H6 of C6, H5 of C5, H5A of C5A, H6A of C6A, H7 of C7, H3 of C3
2. Uiso/Uaniso restraints and constraints
C5 \\sim C6: within 2A with sigma of 0.04 and sigma for terminal atoms of 0.08
C5A \\sim C6A: within 2A with sigma of 0.04 and sigma for terminal atoms of 0.08
3. Rigid body (RIGU) restrains
 C5, C6
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 C5A, C6A
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
4. Others
 Sof(C5A)=Sof(H5A)=Sof(C6A)=Sof(H6A)=1-FVAR(1)
 Sof(C6)=Sof(H6)=Sof(C5)=Sof(H5)=FVAR(1)
5.a Ternary CH refined with riding coordinates:
 C7(H7)
5.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C2(H2), C6(H6), C5(H5), C5A(H5A), C6A(H6A)
5.c Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C), C13(H13A,H13B,H13C), C14(H14A,H14B,H14C), C12(H12A,H12B,
 H12C)
;
_atom_sites_solution_hydrogens   mixed
_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
Br1 Br 0.23236(7) 0.52933(6) -0.02463(7) 0.0872(3) Uani 1 1 d . . . . .
S1 S 0.19991(13) 0.54577(10) 0.62733(12) 0.0450(4) Uani 1 1 d . . . . .
Cl2 Cl 0.12908(14) 0.26332(12) 0.38989(16) 0.0747(5) Uani 1 1 d . . . . .
Cl1 Cl 0.26636(17) 0.28793(11) 0.66105(15) 0.0757(5) Uani 1 1 d . . . . .
O2 O 0.0953(3) 0.5406(2) 0.6494(3) 0.0503(9) Uani 1 1 d . . . . .
O3 O 0.3611(3) 0.1871(3) 0.4627(4) 0.0594(10) Uani 1 1 d . . . . .
O1 O 0.3193(3) 0.5274(3) 0.7295(3) 0.0571(10) Uani 1 1 d . . . . .
N1 N 0.1737(4) 0.4705(3) 0.5145(4) 0.0465(12) Uani 1 1 d . . . . .
O4 O 0.4781(4) 0.3029(3) 0.5866(4) 0.0844(14) Uani 1 1 d . . . . .
C7 C 0.2668(4) 0.4222(4) 0.4962(4) 0.0434(13) Uani 1 1 d . . . . .
H7 H 0.346118 0.445137 0.562548 0.052 Uiso 1 1 calc R . . . .
C9 C 0.3801(6) 0.2669(4) 0.5250(5) 0.0528(15) Uani 1 1 d . . . . .
C11 C 0.2023(5) 0.6635(4) 0.5693(5) 0.0522(15) Uani 1 1 d . . . . .
C3 C 0.3553(6) 0.4753(4) 0.2349(6) 0.0581(16) Uani 1 1 d . . . . .
H3 H 0.425669 0.477300 0.225660 0.070 Uiso 1 1 calc R . . . .
C2 C 0.3630(5) 0.4512(4) 0.3515(5) 0.0537(15) Uani 1 1 d . . . . .
H2 H 0.438810 0.437285 0.420082 0.064 Uiso 1 1 calc R . . . .
C1 C 0.2595(5) 0.4478(4) 0.3665(5) 0.0493(14) Uani 1 1 d . . . . .
C4 C 0.2471(6) 0.4956(5) 0.1364(6) 0.0659(18) Uani 1 1 d . . . . .
C10 C 0.4681(5) 0.1369(4) 0.4742(6) 0.0732(19) Uani 1 1 d . . . . .
H10A H 0.442874 0.079781 0.424092 0.110 Uiso 1 1 calc GR . . . .
H10B H 0.520206 0.120750 0.561764 0.110 Uiso 1 1 calc GR . . . .
H10C H 0.511982 0.176909 0.444318 0.110 Uiso 1 1 calc GR . . . .
C8 C 0.2640(5) 0.3134(4) 0.5139(5) 0.0515(14) Uani 1 1 d . . . . .
C13 C 0.0826(6) 0.6825(4) 0.4483(6) 0.0725(19) Uani 1 1 d . . . . .
H13A H 0.077007 0.641108 0.381731 0.109 Uiso 1 1 calc GR . . . .
H13B H 0.080696 0.747609 0.422793 0.109 Uiso 1 1 calc GR . . . .
H13C H 0.014835 0.670849 0.464430 0.109 Uiso 1 1 calc GR . . . .
C14 C 0.2149(6) 0.7324(4) 0.6751(6) 0.0751(19) Uani 1 1 d . . . . .
H14A H 0.147562 0.723437 0.692590 0.113 Uiso 1 1 calc GR . . . .
H14B H 0.214810 0.796809 0.648001 0.113 Uiso 1 1 calc GR . . . .
H14C H 0.290365 0.720006 0.750757 0.113 Uiso 1 1 calc GR . . . .
C12 C 0.3112(6) 0.6716(4) 0.5433(7) 0.077(2) Uani 1 1 d . . . . .
H12A H 0.385474 0.659599 0.620378 0.116 Uiso 1 1 calc GR . . . .
H12B H 0.313801 0.734580 0.513248 0.116 Uiso 1 1 calc GR . . . .
H12C H 0.302898 0.625838 0.479915 0.116 Uiso 1 1 calc GR . . . .
C6 C 0.153(2) 0.486(2) 0.2695(19) 0.056(5) Uani 0.61(5) 1 d . U P A 1
H6 H 0.084905 0.493324 0.282293 0.067 Uiso 0.61(5) 1 calc R . P A 1
C5 C 0.1449(18) 0.512(2) 0.1543(15) 0.054(4) Uani 0.61(5) 1 d . U P A 1
H5 H 0.074346 0.540426 0.091088 0.065 Uiso 0.61(5) 1 calc R . P A 1
C5A C 0.142(3) 0.461(5) 0.143(3) 0.060(10) Uani 0.39(5) 1 d . U P A 2
H5A H 0.069493 0.451671 0.068092 0.072 Uiso 0.39(5) 1 calc R . P A 2
C6A C 0.147(3) 0.440(4) 0.257(3) 0.060(9) Uani 0.39(5) 1 d . U P A 2
H6A H 0.077586 0.420945 0.261266 0.072 Uiso 0.39(5) 1 calc R . P A 2
H1 H 0.104(6) 0.459(5) 0.469(6) 0.090 Uiso 1 1 d 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
Br1 C4 1.901(6) . ?
S1 O2 1.442(3) . ?
S1 O1 1.427(4) . ?
S1 N1 1.619(4) . ?
S1 C11 1.798(5) . ?
Cl2 C8 1.772(6) . ?
Cl1 C8 1.777(5) . ?
O3 C9 1.302(6) . ?
O3 C10 1.450(6) . ?
N1 C7 1.441(6) . ?
O4 C9 1.196(6) . ?
C7 C1 1.547(7) . ?
C7 C8 1.545(7) . ?
C9 C8 1.528(7) . ?
C11 C13 1.527(7) . ?
C11 C14 1.538(7) . ?
C11 C12 1.525(7) . ?
C3 C2 1.389(7) . ?
C3 C4 1.331(8) . ?
C2 C1 1.378(7) . ?
C1 C6 1.39(2) . ?
C1 C6A 1.39(4) . ?
C4 C5 1.40(2) . ?
C4 C5A 1.42(4) . ?
C6 C5 1.38(2) . ?
C5A C6A 1.36(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O2 S1 N1 105.9(2) . . ?
O2 S1 C11 107.3(2) . . ?
O1 S1 O2 119.6(2) . . ?
O1 S1 N1 108.1(2) . . ?
O1 S1 C11 107.2(2) . . ?
N1 S1 C11 108.3(2) . . ?
C9 O3 C10 117.0(4) . . ?
C7 N1 S1 124.9(3) . . ?
N1 C7 C1 111.6(4) . . ?
N1 C7 C8 111.9(4) . . ?
C8 C7 C1 111.8(4) . . ?
O3 C9 C8 114.2(5) . . ?
O4 C9 O3 124.8(6) . . ?
O4 C9 C8 121.0(5) . . ?
C13 C11 S1 109.8(4) . . ?
C13 C11 C14 110.0(5) . . ?
C14 C11 S1 106.1(4) . . ?
C12 C11 S1 108.9(4) . . ?
C12 C11 C13 110.7(5) . . ?
C12 C11 C14 111.2(5) . . ?
C4 C3 C2 119.9(5) . . ?
C1 C2 C3 120.7(5) . . ?
C2 C1 C7 121.3(5) . . ?
C2 C1 C6 117.2(11) . . ?
C2 C1 C6A 117.3(14) . . ?
C6 C1 C7 120.4(11) . . ?
C6A C1 C7 118.8(15) . . ?
C3 C4 Br1 121.4(5) . . ?
C3 C4 C5 120.6(9) . . ?
C3 C4 C5A 116.3(11) . . ?
C5 C4 Br1 116.7(9) . . ?
C5A C4 Br1 119.0(12) . . ?
Cl2 C8 Cl1 108.2(3) . . ?
C7 C8 Cl2 110.6(4) . . ?
C7 C8 Cl1 110.0(3) . . ?
C9 C8 Cl2 112.5(4) . . ?
C9 C8 Cl1 104.6(4) . . ?
C9 C8 C7 110.7(4) . . ?
C5 C6 C1 121.7(19) . . ?
C6 C5 C4 117.4(17) . . ?
C6A C5A C4 121(2) . . ?
C5A C6A C1 118(3) . . ?

_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
;
####################################################################### 
# 
# 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_sim_up
_database_code_depnum_ccdc_archive 'CCDC 2064227'
loop_
_audit_author_name
_audit_author_address
'Tetsuo Narumi'
;Shizuoka Univeristy
Japan
;
_audit_update_record             
;
2021-02-22 deposited with the CCDC.	2021-06-09 downloaded from the CCDC.
;
_audit_creation_date             2019-01-31
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C14 H17 Br Cl N O4 S'
_chemical_formula_sum            'C14 H17 Br Cl N O4 S'
_chemical_formula_weight         410.71
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C14 H18 Br Cl2 N O4 S'
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'
Br Br -0.2901 2.4595 '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                   6.5794(9)
_cell_length_b                   8.0509(19)
_cell_length_c                   33.122(6)
_cell_angle_alpha                90
_cell_angle_beta                 90.055(14)
_cell_angle_gamma                90
_cell_volume                     1754.5(6)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2068
_cell_measurement_temperature    293.15
_cell_measurement_theta_max      25.6530
_cell_measurement_theta_min      3.0690
_shelx_estimated_absorpt_T_max   0.353
_shelx_estimated_absorpt_T_min   0.228
_exptl_absorpt_coefficient_mu    2.629
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.48111
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.37a (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.555
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             832
_exptl_crystal_size_max          0.8
_exptl_crystal_size_mid          0.72
_exptl_crystal_size_min          0.5
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1007
_diffrn_reflns_av_unetI/netI     0.0840
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       37
_diffrn_reflns_limit_l_min       -39
_diffrn_reflns_number            9634
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.350
_diffrn_reflns_theta_min         2.604
_diffrn_ambient_temperature      293.15
_diffrn_detector                 'Rigaku Mercury area detector'
_diffrn_detector_area_resol_mean 6.83
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -60.00 120.00   1.00    8.00    --   30.00  54.00   0.00  180
  2  ω    -60.00 114.00   1.00    8.00    --   30.00  54.00 120.00  174
;
_diffrn_measurement_device       'fixed-chi diffractometer'
_diffrn_measurement_device_type  'Rigaku XtaLAB mini'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1055717000
_diffrn_orient_matrix_UB_12      -0.0175931000
_diffrn_orient_matrix_UB_13      0.0010955000
_diffrn_orient_matrix_UB_21      0.0078460000
_diffrn_orient_matrix_UB_22      -0.0087131000
_diffrn_orient_matrix_UB_23      0.0211500000
_diffrn_orient_matrix_UB_31      -0.0207576000
_diffrn_orient_matrix_UB_32      0.0861680000
_diffrn_orient_matrix_UB_33      0.0023866000
_diffrn_radiation_monochromator  'curved graphite'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Sealed X-ray tube'
_diffrn_source_type              'Sealed X-ray tube'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2556
_reflns_number_total             3193
_reflns_odcompleteness_completeness 99.39
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     25.30
_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. Completness statistics refer to single and
 composite reflections containing twin component 1 only.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.37a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.37a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.37a (Rigaku OD, 2019)'
_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    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.497
_refine_diff_density_min         -0.635
_refine_diff_density_rms         0.119
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     204
_refine_ls_number_reflns         3193
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1033
_refine_ls_R_factor_gt           0.0857
_refine_ls_restrained_S_all      1.052
_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)+(0.0884P)²+6.4801P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2062
_refine_ls_wR_factor_ref         0.2216
_refine_special_details          
;
 Refined as a 2-component twin.
;
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 0.802(3)
 0.198(3)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
3.a Ternary CH refined with riding coordinates:
 C7(H7)
3.b Aromatic/amide H refined with riding coordinates:
 C5(H5), C2(H2), C3(H3), C6(H6)
3.c Idealised Me refined as rotating group:
 C12(H12A,H12B,H12C), C10(H10A,H10B,H10C), C13(H13A,H13B,H13C), C14(H14A,H14B,
 H14C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_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
Br1 Br 0.9827(2) 0.83040(18) 0.57486(3) 0.0895(5) Uani 1 1 d . . . . .
S1 S 0.7258(3) 0.8285(3) 0.32926(6) 0.0411(5) Uani 1 1 d . . . . .
Cl1 Cl 0.5348(4) 0.4420(3) 0.40513(7) 0.0610(6) Uani 1 1 d . . . . .
O4 O 0.9776(9) 0.4254(9) 0.33355(18) 0.0534(15) Uani 1 1 d . . . . .
O2 O 0.7962(8) 0.7268(8) 0.29640(18) 0.0483(15) Uani 1 1 d . . . . .
O1 O 0.8483(9) 0.9676(9) 0.3409(2) 0.0595(18) Uani 1 1 d . . . . .
O3 O 0.6502(10) 0.3666(10) 0.3185(2) 0.0624(18) Uani 1 1 d . . . . .
N1 N 0.6976(9) 0.7178(9) 0.37222(19) 0.0384(15) Uani 1 1 d . . . . .
C1 C 0.8949(12) 0.6944(11) 0.4388(2) 0.0433(19) Uani 1 1 d . . . . .
C11 C 0.4651(11) 0.8910(10) 0.3197(2) 0.0371(16) Uani 1 1 d . . . . .
C8 C 0.7239(11) 0.5383(11) 0.3759(2) 0.0422(19) Uani 1 1 d . . . . .
C7 C 0.8766(12) 0.6529(11) 0.3948(3) 0.044(2) Uani 1 1 d . . . . .
H7 H 1.004887 0.660628 0.379877 0.053 Uiso 1 1 calc R . . . .
C9 C 0.7750(13) 0.4372(11) 0.3388(3) 0.0458(19) Uani 1 1 d . . . . .
C5 C 1.1084(15) 0.7108(13) 0.4978(3) 0.056(2) Uani 1 1 d . . . . .
H5 H 1.235047 0.696924 0.509883 0.067 Uiso 1 1 calc R . . . .
C12 C 0.3393(12) 0.7306(12) 0.3143(3) 0.055(2) Uani 1 1 d . . . . .
H12A H 0.406298 0.658620 0.295448 0.083 Uiso 1 1 calc GR . . . .
H12B H 0.206554 0.758225 0.304338 0.083 Uiso 1 1 calc GR . . . .
H12C H 0.326938 0.675242 0.339877 0.083 Uiso 1 1 calc GR . . . .
C4 C 0.9460(16) 0.7720(13) 0.5199(3) 0.057(2) Uani 1 1 d . . . . .
C10 C 1.0414(17) 0.3391(14) 0.2969(3) 0.070(3) Uani 1 1 d . . . . .
H10A H 1.000668 0.402426 0.273666 0.105 Uiso 1 1 calc GR . . . .
H10B H 0.978853 0.231473 0.295904 0.105 Uiso 1 1 calc GR . . . .
H10C H 1.186512 0.326865 0.296940 0.105 Uiso 1 1 calc GR . . . .
C2 C 0.7351(14) 0.7599(14) 0.4605(3) 0.057(2) Uani 1 1 d . . . . .
H2 H 0.609233 0.774938 0.448251 0.069 Uiso 1 1 calc R . . . .
C3 C 0.7625(18) 0.8041(16) 0.5016(3) 0.068(3) Uani 1 1 d . . . . .
H3 H 0.657701 0.854182 0.515922 0.082 Uiso 1 1 calc R . . . .
C13 C 0.4720(15) 0.9910(13) 0.2805(3) 0.058(2) Uani 1 1 d . . . . .
H13A H 0.567718 1.080287 0.283249 0.087 Uiso 1 1 calc GR . . . .
H13B H 0.339577 1.035666 0.274913 0.087 Uiso 1 1 calc GR . . . .
H13C H 0.512862 0.919957 0.258689 0.087 Uiso 1 1 calc GR . . . .
C14 C 0.3886(15) 0.9946(14) 0.3550(3) 0.062(3) Uani 1 1 d . . . . .
H14A H 0.409449 0.934689 0.379731 0.093 Uiso 1 1 calc GR . . . .
H14B H 0.246295 1.016764 0.351561 0.093 Uiso 1 1 calc GR . . . .
H14C H 0.461899 1.097639 0.356018 0.093 Uiso 1 1 calc GR . . . .
C6 C 1.0792(14) 0.6703(13) 0.4574(3) 0.054(2) Uani 1 1 d . . . . .
H6 H 1.186587 0.626003 0.442683 0.065 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
Br1 C4 1.896(9) . ?
S1 O2 1.439(6) . ?
S1 O1 1.433(7) . ?
S1 N1 1.689(7) . ?
S1 C11 1.815(8) . ?
Cl1 C8 1.758(8) . ?
O4 C9 1.348(10) . ?
O4 C10 1.461(11) . ?
O3 C9 1.203(11) . ?
N1 C8 1.461(11) . ?
N1 C7 1.489(10) . ?
C1 C7 1.500(12) . ?
C1 C2 1.380(12) . ?
C1 C6 1.374(12) . ?
C11 C12 1.544(11) . ?
C11 C13 1.528(11) . ?
C11 C14 1.523(12) . ?
C8 C7 1.500(13) . ?
C8 C9 1.513(12) . ?
C5 C4 1.385(13) . ?
C5 C6 1.392(13) . ?
C4 C3 1.376(15) . ?
C2 C3 1.416(14) . ?

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
O2 S1 N1 111.9(4) . . ?
O2 S1 C11 109.3(4) . . ?
O1 S1 O2 117.9(4) . . ?
O1 S1 N1 104.3(4) . . ?
O1 S1 C11 111.2(4) . . ?
N1 S1 C11 100.9(3) . . ?
C9 O4 C10 115.1(8) . . ?
C8 N1 S1 125.4(5) . . ?
C8 N1 C7 61.1(5) . . ?
C7 N1 S1 121.4(5) . . ?
C2 C1 C7 122.2(8) . . ?
C6 C1 C7 118.4(7) . . ?
C6 C1 C2 119.5(8) . . ?
C12 C11 S1 107.1(6) . . ?
C13 C11 S1 105.4(6) . . ?
C13 C11 C12 111.1(8) . . ?
C14 C11 S1 109.3(6) . . ?
C14 C11 C12 111.6(7) . . ?
C14 C11 C13 112.0(8) . . ?
N1 C8 Cl1 113.5(5) . . ?
N1 C8 C7 60.3(5) . . ?
N1 C8 C9 119.4(7) . . ?
C7 C8 Cl1 121.0(6) . . ?
C7 C8 C9 121.4(7) . . ?
C9 C8 Cl1 111.6(6) . . ?
N1 C7 C1 118.1(7) . . ?
N1 C7 C8 58.5(5) . . ?
C1 C7 C8 126.6(7) . . ?
O4 C9 C8 111.2(8) . . ?
O3 C9 O4 124.8(8) . . ?
O3 C9 C8 123.7(8) . . ?
C4 C5 C6 119.0(9) . . ?
C5 C4 Br1 119.8(8) . . ?
C3 C4 Br1 119.2(7) . . ?
C3 C4 C5 120.8(9) . . ?
C1 C2 C3 120.1(9) . . ?
C4 C3 C2 119.2(9) . . ?
C1 C6 C5 121.4(8) . . ?

_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 1.728
_oxdiff_exptl_absorpt_empirical_full_min 0.646
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 0.802(3)
2 0.198(3)

_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
####################################################################### 
# 
# 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_imai_20201118_2
_database_code_depnum_ccdc_archive 'CCDC 2064230'
loop_
_audit_author_name
_audit_author_address
'Tetsuo Narumi'
;Shizuoka Univeristy
Japan
;
_audit_update_record             
;
2021-02-22 deposited with the CCDC.	2021-06-09 downloaded from the CCDC.
;
_audit_creation_date             2020-12-17
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6226)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C17 H29 Cl N O4 S, C12 H24 N, 0.5(C6 H14)'
_chemical_formula_sum            'C32 H60 Cl N2 O4 S'
_chemical_formula_weight         604.33
_chemical_melting_point          ?
_chemical_oxdiff_formula         C25H39ClN2O3S
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           15
_space_group_name_H-M_alt        'I 1 2/a 1'
_space_group_name_Hall           '-I 2ya'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y, -z'
'x+1/2, y+1/2, z+1/2'
'-x+1, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y, z'
'-x+1/2, -y+1/2, -z+1/2'
'x, -y+1/2, z+1/2'

_cell_length_a                   14.1676(19)
_cell_length_b                   21.601(3)
_cell_length_c                   23.423(4)
_cell_angle_alpha                90
_cell_angle_beta                 94.248(13)
_cell_angle_gamma                90
_cell_volume                     7148.8(17)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    4632
_cell_measurement_temperature    293
_cell_measurement_theta_max      24.0460
_cell_measurement_theta_min      2.3540
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.200
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.75753
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.92a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.123
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       hexagonal
_exptl_crystal_F_000             2648
_exptl_crystal_size_max          0.354
_exptl_crystal_size_mid          0.225
_exptl_crystal_size_min          0.145
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0845
_diffrn_reflns_av_unetI/netI     0.0646
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            31587
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.349
_diffrn_reflns_theta_min         2.374
_diffrn_ambient_temperature      293
_diffrn_detector                 'Rigaku Mercury area detector'
_diffrn_detector_area_resol_mean 6.83
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -60.00 120.00   1.00  120.00    --   30.00  54.00   0.00  180
  2  ω    -60.00 120.00   1.00  120.00    --   30.00  54.00 120.00  180
  3  ω    -60.00 120.00   1.00  120.00    --   30.00  54.00 240.00  180
;
_diffrn_measurement_device       'fixed-chi diffractometer'
_diffrn_measurement_device_type  'Rigaku XtaLAB mini'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0366654000
_diffrn_orient_matrix_UB_12      0.0060305000
_diffrn_orient_matrix_UB_13      0.0182798000
_diffrn_orient_matrix_UB_21      -0.0324604000
_diffrn_orient_matrix_UB_22      0.0040573000
_diffrn_orient_matrix_UB_23      -0.0242476000
_diffrn_orient_matrix_UB_31      -0.0110550000
_diffrn_orient_matrix_UB_32      -0.0320182000
_diffrn_orient_matrix_UB_33      0.0003770000
_diffrn_radiation_monochromator  'curved graphite'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Sealed X-ray tube'
_diffrn_source_type              'Sealed X-ray tube'
_diffrn_special_details          ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3296
_reflns_number_total             6551
_reflns_odcompleteness_completeness 99.96
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     25.29
_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 1.171.41.92a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.41.92a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.41.92a (Rigaku OD, 2020)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_refine_diff_density_max         0.311
_refine_diff_density_min         -0.226
_refine_diff_density_rms         0.041
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.017
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     382
_refine_ls_number_reflns         6551
_refine_ls_number_restraints     67
_refine_ls_R_factor_all          0.1362
_refine_ls_R_factor_gt           0.0619
_refine_ls_restrained_S_all      1.015
_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)+(0.0861P)²+0.4865P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1515
_refine_ls_wR_factor_ref         0.1905
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups, All N(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 C33-C34 \\sim C35-C34 \\sim C33-C32 \\sim C32-C31 \\sim C30-C31
 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
C35 \\sim C34 \\sim C33 \\sim C32 \\sim C31 \\sim C30: within 2A with sigma of
0.04 and sigma for terminal atoms of 0.08 within 2A
4. Rigid body (RIGU) restrains
 C35, C31, H31A, H31B, C32, C30, C33, H32A, H32B, H30A, H30B, H30C, H33A, H33B,
  C34, H34A, H34B, H35A, H35B, H35C
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
5. Others
 Fixed Sof: C31(0.5) H31A(0.5) H31B(0.5) C33(0.5) H33A(0.5) H33B(0.5)
 H35A(0.5) H35B(0.5) H35C(0.5) C34(0.5) H34A(0.5) H34B(0.5) C32(0.5) H32A(0.5)
 H32B(0.5) H30A(0.5) H30B(0.5) H30C(0.5)
6.a Riding coordinates:
 N1(H1)
6.b Ternary CH refined with riding coordinates:
 C2(H2), C18(H18), C24(H24), C11(H11)
6.c Secondary CH2 refined with riding coordinates:
 N2(H2A,H2B), C10(H10A,H10B), C9(H9A,H9B), C29(H29A,H29B), C23(H23A,H23B),
 C25(H25A,H25B), C6(H6A,H6B), C19(H19A,H19B), C26(H26A,H26B), C27(H27A,H27B),
 C20(H20A,H20B), C21(H21A,H21B), C22(H22A,H22B), C7(H7A,H7B), C28(H28A,H28B),
 C8(H8A,H8B), C31(H31A,H31B), C33(H33A,H33B), C34(H34A,H34B), C32(H32A,H32B)
6.d Me refined with riding coordinates:
 C16(H16A,H16B,H16C), C17(H17A,H17B,H17C), C15(H15A,H15B,H15C), C12(H12A,H12B,
 H12C), C13(H13A,H13B,H13C)
6.e Aromatic/amide H refined with riding coordinates:
 C3(H3)
6.f Idealised Me refined as rotating group:
 C35(H35A,H35B,H35C), C30(H30A,H30B,H30C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_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 0.03238(6) 0.50246(4) 0.17335(4) 0.0650(3) Uani 1 1 d . . . . .
Cl1 Cl 0.12006(6) 0.50008(5) 0.33226(5) 0.0815(3) Uani 1 1 d . . . . .
O3 O 0.29400(14) 0.32493(10) 0.27500(10) 0.0639(6) Uani 1 1 d . . . . .
O4 O 0.42299(15) 0.37808(10) 0.26729(10) 0.0631(6) Uani 1 1 d . . . . .
N2 N 0.38478(17) 0.21507(11) 0.25828(11) 0.0538(7) Uani 1 1 d . . . . .
H2A H 0.365768 0.253986 0.262348 0.065 Uiso 1 1 calc R U . . .
H2B H 0.333881 0.192907 0.246863 0.065 Uiso 1 1 calc R U . . .
O1 O -0.03588(17) 0.46713(11) 0.20010(11) 0.0792(7) Uani 1 1 d . . . . .
N1 N 0.06782(18) 0.55929(11) 0.21314(12) 0.0607(7) Uani 1 1 d . . . . .
H1 H 0.027977 0.564855 0.238671 0.073 Uiso 1 1 d R U . . .
O2 O 0.11234(18) 0.47161(12) 0.15533(13) 0.0908(9) Uani 1 1 d . . . . .
C1 C 0.3429(2) 0.37275(14) 0.28260(12) 0.0459(7) Uani 1 1 d . . . . .
C2 C 0.2994(2) 0.42568(14) 0.31406(14) 0.0518(8) Uani 1 1 d . . . . .
H2 H 0.243594 0.409746 0.331641 0.062 Uiso 1 1 calc R U . . .
C3 C 0.2681(2) 0.47584(14) 0.27437(14) 0.0544(8) Uani 1 1 d . . . . .
H3 H 0.304952 0.482814 0.243776 0.065 Uiso 1 1 calc R U . . .
C4 C 0.1942(2) 0.51158(14) 0.27744(15) 0.0555(8) Uani 1 1 d . . . . .
C18 C 0.4504(2) 0.21380(16) 0.21176(15) 0.0615(9) Uani 1 1 d . . . . .
H18 H 0.504465 0.240636 0.222750 0.074 Uiso 1 1 calc R U . . .
C24 C 0.4206(2) 0.19208(16) 0.31529(15) 0.0640(9) Uani 1 1 d . . . . .
H24 H 0.442236 0.149326 0.311254 0.077 Uiso 1 1 calc R U . . .
C5 C 0.1649(2) 0.56635(15) 0.24069(17) 0.0646(10) Uani 1 1 d . . . . .
C10 C 0.3675(2) 0.45088(18) 0.36131(16) 0.0701(10) Uani 1 1 d . . . . .
H10A H 0.337419 0.485370 0.379321 0.084 Uiso 1 1 calc R U . . .
H10B H 0.422860 0.466818 0.344244 0.084 Uiso 1 1 calc R U . . .
C9 C 0.1614(3) 0.62563(16) 0.2763(2) 0.0866(13) Uani 1 1 d . . . . .
H9A H 0.101115 0.629063 0.293101 0.104 Uiso 1 1 calc R U . . .
H9B H 0.211599 0.625628 0.306789 0.104 Uiso 1 1 calc R U . . .
C14 C -0.0295(3) 0.53718(19) 0.11197(16) 0.0818(12) Uani 1 1 d . . . . .
C11 C 0.3996(3) 0.4045(2) 0.40728(16) 0.0837(12) Uani 1 1 d . . . . .
H11 H 0.430828 0.370031 0.388961 0.100 Uiso 1 1 calc R U . . .
C29 C 0.5028(3) 0.2307(2) 0.33858(18) 0.0862(12) Uani 1 1 d . . . . .
H29A H 0.553988 0.227584 0.313439 0.103 Uiso 1 1 calc R U . . .
H29B H 0.483752 0.273749 0.340134 0.103 Uiso 1 1 calc R U . . .
C23 C 0.4861(3) 0.15038(19) 0.2024(2) 0.0900(13) Uani 1 1 d . . . . .
H23A H 0.433045 0.122262 0.195746 0.108 Uiso 1 1 calc R U . . .
H23B H 0.523518 0.136630 0.236399 0.108 Uiso 1 1 calc R U . . .
C25 C 0.3420(3) 0.1925(2) 0.35410(16) 0.0816(11) Uani 1 1 d . . . . .
H25A H 0.291874 0.165235 0.338834 0.098 Uiso 1 1 calc R U . . .
H25B H 0.316188 0.234006 0.355771 0.098 Uiso 1 1 calc R U . . .
C6 C 0.2342(3) 0.58343(17) 0.1975(2) 0.0847(12) Uani 1 1 d . . . . .
H6A H 0.298054 0.571896 0.211147 0.102 Uiso 1 1 calc R U . . .
H6B H 0.218216 0.562738 0.161269 0.102 Uiso 1 1 calc R U . . .
C19 C 0.3998(3) 0.2395(2) 0.15939(17) 0.0829(12) Uani 1 1 d . . . . .
H19A H 0.381862 0.282001 0.166480 0.099 Uiso 1 1 calc R U . . .
H19B H 0.342355 0.215932 0.150387 0.099 Uiso 1 1 calc R U . . .
C16 C -0.1109(3) 0.5754(2) 0.13083(19) 0.1027(15) Uani 1 1 d . . . . .
H16A H -0.086717 0.608758 0.154736 0.154 Uiso 1 1 calc R U . . .
H16B H -0.146373 0.591967 0.097798 0.154 Uiso 1 1 calc R U . . .
H16C H -0.151367 0.549777 0.151947 0.154 Uiso 1 1 calc R U . . .
C26 C 0.3754(4) 0.1717(2) 0.4138(2) 0.1073(16) Uani 1 1 d . . . . .
H26A H 0.393109 0.128330 0.412874 0.129 Uiso 1 1 calc R U . . .
H26B H 0.324125 0.175868 0.438699 0.129 Uiso 1 1 calc R U . . .
C27 C 0.4596(5) 0.2096(3) 0.4376(2) 0.1218(19) Uani 1 1 d . . . . .
H27A H 0.439769 0.251918 0.443697 0.146 Uiso 1 1 calc R U . . .
H27B H 0.483506 0.192670 0.474176 0.146 Uiso 1 1 calc R U . . .
C20 C 0.4600(4) 0.2377(3) 0.1089(2) 0.1122(16) Uani 1 1 d . . . . .
H20A H 0.423358 0.252501 0.075037 0.135 Uiso 1 1 calc R U . . .
H20B H 0.514087 0.264822 0.116103 0.135 Uiso 1 1 calc R U . . .
C21 C 0.4931(4) 0.1741(3) 0.0988(2) 0.1226(19) Uani 1 1 d . . . . .
H21A H 0.534051 0.174254 0.067432 0.147 Uiso 1 1 calc R U . . .
H21B H 0.439248 0.147747 0.088214 0.147 Uiso 1 1 calc R U . . .
C22 C 0.5462(4) 0.1488(3) 0.1516(2) 0.1193(18) Uani 1 1 d . . . . .
H22A H 0.603106 0.173057 0.160153 0.143 Uiso 1 1 calc R U . . .
H22B H 0.565049 0.106473 0.144571 0.143 Uiso 1 1 calc R U . . .
C7 C 0.2260(4) 0.6522(2) 0.1907(3) 0.127(2) Uani 1 1 d . . . . .
H7A H 0.288409 0.670814 0.191927 0.152 Uiso 1 1 calc R U . . .
H7B H 0.192745 0.662252 0.154136 0.152 Uiso 1 1 calc R U . . .
C17 C -0.0665(4) 0.4844(2) 0.0743(2) 0.1142(16) Uani 1 1 d . . . . .
H17A H -0.014232 0.460435 0.062524 0.171 Uiso 1 1 calc R U . . .
H17B H -0.106798 0.458564 0.095239 0.171 Uiso 1 1 calc R U . . .
H17C H -0.101804 0.500754 0.041091 0.171 Uiso 1 1 calc R U . . .
C28 C 0.5362(4) 0.2090(3) 0.3972(2) 0.1248(18) Uani 1 1 d . . . . .
H28A H 0.560817 0.167281 0.394749 0.150 Uiso 1 1 calc R U . . .
H28B H 0.587579 0.235473 0.412224 0.150 Uiso 1 1 calc R U . . .
C15 C 0.0377(4) 0.5772(3) 0.0808(2) 0.129(2) Uani 1 1 d . . . . .
H15A H 0.088986 0.552326 0.069133 0.194 Uiso 1 1 calc R U . . .
H15B H 0.004477 0.595285 0.047702 0.194 Uiso 1 1 calc R U . . .
H15C H 0.062320 0.609508 0.105881 0.194 Uiso 1 1 calc R U . . .
C12 C 0.3207(4) 0.3792(3) 0.4374(2) 0.1225(18) Uani 1 1 d . . . . .
H12A H 0.275756 0.359993 0.410206 0.184 Uiso 1 1 calc R U . . .
H12B H 0.344345 0.349055 0.464912 0.184 Uiso 1 1 calc R U . . .
H12C H 0.290323 0.412121 0.456587 0.184 Uiso 1 1 calc R U . . .
C8 C 0.1736(5) 0.6760(2) 0.2375(3) 0.150(2) Uani 1 1 d . . . . .
H8A H 0.208588 0.709339 0.257087 0.180 Uiso 1 1 calc R U . . .
H8B H 0.112519 0.691794 0.222808 0.180 Uiso 1 1 calc R U . . .
C13 C 0.4710(4) 0.4349(4) 0.4491(2) 0.171(3) Uani 1 1 d . . . . .
H13A H 0.522105 0.451104 0.428838 0.256 Uiso 1 1 calc R U . . .
H13B H 0.441266 0.467983 0.468337 0.256 Uiso 1 1 calc R U . . .
H13C H 0.495288 0.404917 0.476661 0.256 Uiso 1 1 calc R U . . .
C31 C 0.7189(18) 0.2135(10) 0.5215(12) 0.220(9) Uani 0.5 1 d D U P A -1
H31A H 0.650499 0.217295 0.517626 0.264 Uiso 0.5 1 calc R U P A -1
H31B H 0.741114 0.219630 0.561250 0.264 Uiso 0.5 1 calc R U P A -1
C33 C 0.733(4) 0.3175(13) 0.5076(18) 0.271(12) Uani 0.5 1 d D U P A -1
H33A H 0.666942 0.315767 0.515101 0.326 Uiso 0.5 1 calc R U P A -1
H33B H 0.769962 0.326500 0.543253 0.326 Uiso 0.5 1 calc R U P A -1
C35 C 0.750000 0.4224(11) 0.500000 0.339(12) Uani 1 2 d DS TU P . .
H35A H 0.814222 0.435849 0.507846 0.509 Uiso 0.5 1 calc R U P B -1
H35B H 0.722293 0.414123 0.535399 0.509 Uiso 0.5 1 calc R U P B -1
H35C H 0.714467 0.454185 0.479443 0.509 Uiso 0.5 1 calc R U P B -1
C34 C 0.749(2) 0.3658(11) 0.4653(15) 0.291(11) Uani 0.5 1 d D U P A -1
H34A H 0.697361 0.366691 0.435438 0.349 Uiso 0.5 1 calc R U P A -1
H34B H 0.808039 0.359875 0.448132 0.349 Uiso 0.5 1 calc R U P A -1
C32 C 0.764(2) 0.2572(12) 0.4840(15) 0.228(10) Uani 0.5 1 d D U P A -1
H32A H 0.740201 0.252085 0.444310 0.274 Uiso 0.5 1 calc R U P A -1
H32B H 0.832012 0.253008 0.487152 0.274 Uiso 0.5 1 calc R U P A -1
C30 C 0.750000 0.1528(10) 0.500000 0.248(7) Uani 1 2 d DS TU P . .
H30A H 0.698632 0.133818 0.477409 0.373 Uiso 0.5 1 calc R U P A -1
H30B H 0.769118 0.126552 0.531819 0.373 Uiso 0.5 1 calc R U P A -1
H30C H 0.802398 0.158892 0.476857 0.373 Uiso 0.5 1 calc R U P A -1


_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 O1 1.414(2) . ?
S1 N1 1.600(3) . ?
S1 O2 1.406(2) . ?
S1 C14 1.792(4) . ?
Cl1 C4 1.736(3) . ?
O3 C1 1.249(3) . ?
O4 C1 1.221(3) . ?
N2 H2A 0.8900 . ?
N2 H2B 0.8900 . ?
N2 C18 1.484(4) . ?
N2 C24 1.479(4) . ?
N1 H1 0.8606 . ?
N1 C5 1.483(4) . ?
C1 C2 1.516(4) . ?
C2 H2 0.9800 . ?
C2 C3 1.474(4) . ?
C2 C10 1.515(5) . ?
C3 H3 0.9300 . ?
C3 C4 1.306(4) . ?
C4 C5 1.504(5) . ?
C18 H18 0.9800 . ?
C18 C23 1.482(5) . ?
C18 C19 1.482(5) . ?
C24 H24 0.9800 . ?
C24 C29 1.502(5) . ?
C24 C25 1.489(5) . ?
C5 C9 1.531(5) . ?
C5 C6 1.508(5) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C10 C11 1.517(5) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C9 C8 1.435(7) . ?
C14 C16 1.511(5) . ?
C14 C17 1.511(6) . ?
C14 C15 1.514(6) . ?
C11 H11 0.9800 . ?
C11 C12 1.470(6) . ?
C11 C13 1.506(7) . ?
C29 H29A 0.9700 . ?
C29 H29B 0.9700 . ?
C29 C28 1.494(6) . ?
C23 H23A 0.9700 . ?
C23 H23B 0.9700 . ?
C23 C22 1.515(6) . ?
C25 H25A 0.9700 . ?
C25 H25B 0.9700 . ?
C25 C26 1.510(6) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C6 C7 1.498(6) . ?
C19 H19A 0.9700 . ?
C19 H19B 0.9700 . ?
C19 C20 1.508(5) . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C26 H26A 0.9700 . ?
C26 H26B 0.9700 . ?
C26 C27 1.519(7) . ?
C27 H27A 0.9700 . ?
C27 H27B 0.9700 . ?
C27 C28 1.491(7) . ?
C20 H20A 0.9700 . ?
C20 H20B 0.9700 . ?
C20 C21 1.475(7) . ?
C21 H21A 0.9700 . ?
C21 H21B 0.9700 . ?
C21 C22 1.501(7) . ?
C22 H22A 0.9700 . ?
C22 H22B 0.9700 . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C7 C8 1.462(7) . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
C28 H28A 0.9700 . ?
C28 H28B 0.9700 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C31 H31A 0.9700 . ?
C31 H31B 0.9700 . ?
C31 C32 1.466(15) . ?
C31 C30 1.482(15) . ?
C33 H33A 0.9700 . ?
C33 H33B 0.9700 . ?
C33 C34 1.465(18) . ?
C33 C32 1.491(17) . ?
C35 H35A 0.9600 . ?
C35 H35B 0.9600 . ?
C35 H35C 0.9600 . ?
C35 C34 1.466(17) . ?
C34 H34A 0.9700 . ?
C34 H34B 0.9700 . ?
C32 H32A 0.9700 . ?
C32 H32B 0.9700 . ?
C30 H30A 0.9600 . ?
C30 H30B 0.9600 . ?
C30 H30C 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
O1 S1 N1 110.58(16) . . ?
O1 S1 C14 105.74(18) . . ?
N1 S1 C14 105.07(17) . . ?
O2 S1 O1 118.03(17) . . ?
O2 S1 N1 108.28(15) . . ?
O2 S1 C14 108.34(19) . . ?
H2A N2 H2B 107.2 . . ?
C18 N2 H2A 107.9 . . ?
C18 N2 H2B 107.9 . . ?
C24 N2 H2A 107.9 . . ?
C24 N2 H2B 107.9 . . ?
C24 N2 C18 117.7(2) . . ?
S1 N1 H1 108.6 . . ?
C5 N1 S1 125.0(2) . . ?
C5 N1 H1 108.5 . . ?
O3 C1 C2 116.9(3) . . ?
O4 C1 O3 123.6(3) . . ?
O4 C1 C2 119.5(3) . . ?
C1 C2 H2 108.0 . . ?
C3 C2 C1 111.2(3) . . ?
C3 C2 H2 108.0 . . ?
C3 C2 C10 110.0(3) . . ?
C10 C2 C1 111.5(3) . . ?
C10 C2 H2 108.0 . . ?
C2 C3 H3 116.4 . . ?
C4 C3 C2 127.2(3) . . ?
C4 C3 H3 116.4 . . ?
C3 C4 Cl1 119.2(3) . . ?
C3 C4 C5 128.5(3) . . ?
C5 C4 Cl1 112.3(2) . . ?
N2 C18 H18 108.4 . . ?
C23 C18 N2 111.4(3) . . ?
C23 C18 H18 108.4 . . ?
C19 C18 N2 108.1(3) . . ?
C19 C18 H18 108.4 . . ?
C19 C18 C23 111.9(3) . . ?
N2 C24 H24 108.6 . . ?
N2 C24 C29 110.3(3) . . ?
N2 C24 C25 109.1(3) . . ?
C29 C24 H24 108.6 . . ?
C25 C24 H24 108.6 . . ?
C25 C24 C29 111.7(3) . . ?
N1 C5 C4 112.1(3) . . ?
N1 C5 C9 104.9(3) . . ?
N1 C5 C6 111.2(3) . . ?
C4 C5 C9 111.4(3) . . ?
C4 C5 C6 114.3(3) . . ?
C6 C5 C9 102.1(3) . . ?
C2 C10 H10A 108.5 . . ?
C2 C10 H10B 108.5 . . ?
C2 C10 C11 115.0(3) . . ?
H10A C10 H10B 107.5 . . ?
C11 C10 H10A 108.5 . . ?
C11 C10 H10B 108.5 . . ?
C5 C9 H9A 110.5 . . ?
C5 C9 H9B 110.5 . . ?
H9A C9 H9B 108.7 . . ?
C8 C9 C5 106.2(4) . . ?
C8 C9 H9A 110.5 . . ?
C8 C9 H9B 110.5 . . ?
C16 C14 S1 109.4(3) . . ?
C16 C14 C17 110.1(4) . . ?
C16 C14 C15 110.5(4) . . ?
C17 C14 S1 106.3(3) . . ?
C17 C14 C15 110.6(4) . . ?
C15 C14 S1 109.8(3) . . ?
C10 C11 H11 108.2 . . ?
C12 C11 C10 112.7(4) . . ?
C12 C11 H11 108.2 . . ?
C12 C11 C13 110.4(4) . . ?
C13 C11 C10 109.0(4) . . ?
C13 C11 H11 108.2 . . ?
C24 C29 H29A 109.6 . . ?
C24 C29 H29B 109.6 . . ?
H29A C29 H29B 108.1 . . ?
C28 C29 C24 110.2(4) . . ?
C28 C29 H29A 109.6 . . ?
C28 C29 H29B 109.6 . . ?
C18 C23 H23A 109.5 . . ?
C18 C23 H23B 109.5 . . ?
C18 C23 C22 110.8(4) . . ?
H23A C23 H23B 108.1 . . ?
C22 C23 H23A 109.5 . . ?
C22 C23 H23B 109.5 . . ?
C24 C25 H25A 109.3 . . ?
C24 C25 H25B 109.3 . . ?
C24 C25 C26 111.4(3) . . ?
H25A C25 H25B 108.0 . . ?
C26 C25 H25A 109.3 . . ?
C26 C25 H25B 109.3 . . ?
C5 C6 H6A 110.7 . . ?
C5 C6 H6B 110.7 . . ?
H6A C6 H6B 108.8 . . ?
C7 C6 C5 105.3(3) . . ?
C7 C6 H6A 110.7 . . ?
C7 C6 H6B 110.7 . . ?
C18 C19 H19A 109.2 . . ?
C18 C19 H19B 109.2 . . ?
C18 C19 C20 111.9(3) . . ?
H19A C19 H19B 107.9 . . ?
C20 C19 H19A 109.2 . . ?
C20 C19 H19B 109.2 . . ?
C14 C16 H16A 109.5 . . ?
C14 C16 H16B 109.5 . . ?
C14 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C25 C26 H26A 109.4 . . ?
C25 C26 H26B 109.4 . . ?
C25 C26 C27 111.3(4) . . ?
H26A C26 H26B 108.0 . . ?
C27 C26 H26A 109.4 . . ?
C27 C26 H26B 109.4 . . ?
C26 C27 H27A 109.5 . . ?
C26 C27 H27B 109.5 . . ?
H27A C27 H27B 108.1 . . ?
C28 C27 C26 110.6(4) . . ?
C28 C27 H27A 109.5 . . ?
C28 C27 H27B 109.5 . . ?
C19 C20 H20A 109.5 . . ?
C19 C20 H20B 109.5 . . ?
H20A C20 H20B 108.1 . . ?
C21 C20 C19 110.8(4) . . ?
C21 C20 H20A 109.5 . . ?
C21 C20 H20B 109.5 . . ?
C20 C21 H21A 109.5 . . ?
C20 C21 H21B 109.5 . . ?
C20 C21 C22 110.7(4) . . ?
H21A C21 H21B 108.1 . . ?
C22 C21 H21A 109.5 . . ?
C22 C21 H21B 109.5 . . ?
C23 C22 H22A 109.4 . . ?
C23 C22 H22B 109.4 . . ?
C21 C22 C23 111.2(4) . . ?
C21 C22 H22A 109.4 . . ?
C21 C22 H22B 109.4 . . ?
H22A C22 H22B 108.0 . . ?
C6 C7 H7A 110.1 . . ?
C6 C7 H7B 110.1 . . ?
H7A C7 H7B 108.4 . . ?
C8 C7 C6 107.9(4) . . ?
C8 C7 H7A 110.1 . . ?
C8 C7 H7B 110.1 . . ?
C14 C17 H17A 109.5 . . ?
C14 C17 H17B 109.5 . . ?
C14 C17 H17C 109.5 . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C29 C28 H28A 109.1 . . ?
C29 C28 H28B 109.1 . . ?
C27 C28 C29 112.6(4) . . ?
C27 C28 H28A 109.1 . . ?
C27 C28 H28B 109.1 . . ?
H28A C28 H28B 107.8 . . ?
C14 C15 H15A 109.5 . . ?
C14 C15 H15B 109.5 . . ?
C14 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C9 C8 C7 107.5(4) . . ?
C9 C8 H8A 110.2 . . ?
C9 C8 H8B 110.2 . . ?
C7 C8 H8A 110.2 . . ?
C7 C8 H8B 110.2 . . ?
H8A C8 H8B 108.5 . . ?
C11 C13 H13A 109.5 . . ?
C11 C13 H13B 109.5 . . ?
C11 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
H31A C31 H31B 109.2 . . ?
C32 C31 H31A 111.3 . . ?
C32 C31 H31B 111.3 . . ?
C32 C31 C30 102(2) . . ?
C30 C31 H31A 111.3 . . ?
C30 C31 H31B 111.3 . . ?
H33A C33 H33B 108.4 . . ?
C34 C33 H33A 110.1 . . ?
C34 C33 H33B 110.1 . . ?
C34 C33 C32 108(2) . . ?
C32 C33 H33A 110.1 . . ?
C32 C33 H33B 110.1 . . ?
H35A C35 H35B 109.5 . . ?
H35A C35 H35C 109.5 . . ?
H35B C35 H35C 109.5 . . ?
C34 C35 H35A 109.5 . . ?
C34 C35 H35B 109.5 . . ?
C34 C35 H35C 109.5 . . ?
C33 C34 C35 102(3) . . ?
C33 C34 H34A 111.3 . . ?
C33 C34 H34B 111.3 . . ?
C35 C34 H34A 111.3 . . ?
C35 C34 H34B 111.3 . . ?
H34A C34 H34B 109.2 . . ?
C31 C32 C33 101.0(18) . . ?
C31 C32 H32A 111.6 . . ?
C31 C32 H32B 111.6 . . ?
C33 C32 H32A 111.6 . . ?
C33 C32 H32B 111.6 . . ?
H32A C32 H32B 109.4 . . ?
C31 C30 H30A 109.5 . . ?
C31 C30 H30B 109.5 . . ?
C31 C30 H30C 109.5 . . ?
H30A C30 H30B 109.5 . . ?
H30A C30 H30C 109.5 . . ?
H30B C30 H30C 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 N1 C5 C4 -56.0(4) . . . . ?
S1 N1 C5 C9 -177.0(3) . . . . ?
S1 N1 C5 C6 73.3(3) . . . . ?
Cl1 C4 C5 N1 -60.0(3) . . . . ?
Cl1 C4 C5 C9 57.2(3) . . . . ?
Cl1 C4 C5 C6 172.3(3) . . . . ?
O3 C1 C2 C3 -105.1(3) . . . . ?
O3 C1 C2 C10 131.7(3) . . . . ?
O4 C1 C2 C3 76.5(3) . . . . ?
O4 C1 C2 C10 -46.7(4) . . . . ?
N2 C18 C23 C22 175.2(4) . . . . ?
N2 C18 C19 C20 -177.7(3) . . . . ?
N2 C24 C29 C28 177.6(4) . . . . ?
N2 C24 C25 C26 -177.9(4) . . . . ?
O1 S1 N1 C5 113.3(3) . . . . ?
O1 S1 C14 C16 57.6(3) . . . . ?
O1 S1 C14 C17 -61.3(3) . . . . ?
O1 S1 C14 C15 178.9(3) . . . . ?
N1 S1 C14 C16 -59.4(3) . . . . ?
N1 S1 C14 C17 -178.3(3) . . . . ?
N1 S1 C14 C15 61.9(3) . . . . ?
N1 C5 C9 C8 -82.7(4) . . . . ?
N1 C5 C6 C7 83.5(4) . . . . ?
O2 S1 N1 C5 -17.4(3) . . . . ?
O2 S1 C14 C16 -175.0(3) . . . . ?
O2 S1 C14 C17 66.1(3) . . . . ?
O2 S1 C14 C15 -53.6(4) . . . . ?
C1 C2 C3 C4 145.2(3) . . . . ?
C1 C2 C10 C11 -60.1(4) . . . . ?
C2 C3 C4 Cl1 -1.7(5) . . . . ?
C2 C3 C4 C5 174.4(3) . . . . ?
C2 C10 C11 C12 -60.4(5) . . . . ?
C2 C10 C11 C13 176.6(4) . . . . ?
C3 C2 C10 C11 176.0(3) . . . . ?
C3 C4 C5 N1 123.6(4) . . . . ?
C3 C4 C5 C9 -119.2(4) . . . . ?
C3 C4 C5 C6 -4.1(5) . . . . ?
C4 C5 C9 C8 155.8(4) . . . . ?
C4 C5 C6 C7 -148.4(4) . . . . ?
C18 N2 C24 C29 61.6(4) . . . . ?
C18 N2 C24 C25 -175.4(3) . . . . ?
C18 C23 C22 C21 -55.0(6) . . . . ?
C18 C19 C20 C21 55.8(6) . . . . ?
C24 N2 C18 C23 57.3(4) . . . . ?
C24 N2 C18 C19 -179.3(3) . . . . ?
C24 C29 C28 C27 -56.5(6) . . . . ?
C24 C25 C26 C27 54.2(5) . . . . ?
C5 C9 C8 C7 -25.8(6) . . . . ?
C5 C6 C7 C8 13.6(6) . . . . ?
C10 C2 C3 C4 -90.8(4) . . . . ?
C9 C5 C6 C7 -27.9(5) . . . . ?
C14 S1 N1 C5 -133.0(3) . . . . ?
C29 C24 C25 C26 -55.7(5) . . . . ?
C23 C18 C19 C20 -54.6(5) . . . . ?
C25 C24 C29 C28 56.1(5) . . . . ?
C25 C26 C27 C28 -53.6(6) . . . . ?
C6 C5 C9 C8 33.4(5) . . . . ?
C6 C7 C8 C9 7.7(7) . . . . ?
C19 C18 C23 C22 54.0(5) . . . . ?
C19 C20 C21 C22 -56.5(6) . . . . ?
C26 C27 C28 C29 55.4(6) . . . . ?
C20 C21 C22 C23 56.7(6) . . . . ?
C34 C33 C32 C31 -164(3) . . . . ?
C32 C33 C34 C35 -160(3) . . . . ?
C30 C31 C32 C33 -179(3) . . . . ?

_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 1.531
_oxdiff_exptl_absorpt_empirical_full_min 0.665
