# Supplementary Information (SI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2024

####################################################################### 
# 
# 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. 
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data_RS206_0m
_database_code_depnum_ccdc_archive 'CCDC 2384417'
loop_
_audit_author_name
_audit_author_address
'Matthias Zeller '
;Purdue University  
United States of America
;
_audit_update_record             
;
2024-09-16 deposited with the CCDC.	2024-11-19 downloaded from the CCDC.
;


_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C7 H4 N O3 S, 2(C7 H13 Cl N), Cl'
_chemical_formula_sum            'C21 H30 Cl3 N3 O3 S'
_chemical_formula_weight         510.89

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'

_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.
;

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

_cell_length_a                   11.2805(14)
_cell_length_b                   10.9819(18)
_cell_length_c                   38.981(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     4829.0(11)
_cell_formula_units_Z            8
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    9325
_cell_measurement_theta_min      4.5373
_cell_measurement_theta_max      80.3224

_exptl_crystal_description       plate
_exptl_crystal_colour            'light yellow'
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.405
_exptl_crystal_F_000             2144
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.050
_exptl_crystal_size_min          0.020
_exptl_absorpt_coefficient_mu    4.478
_shelx_estimated_absorpt_T_min   0.468
_shelx_estimated_absorpt_T_max   0.916
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5830
_exptl_absorpt_correction_T_max  0.7543
_exptl_absorpt_process_details   
;
 SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
 J. Appl. Cryst. 48 (2015) 3-10
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   'I-mu-S microsource X-ray tube'
_diffrn_source_current           '1.0 mA'
_diffrn_source_voltage           '50 kV'
_diffrn_radiation_monochromator  'laterally graded multilayer (Goebel) mirror'
_diffrn_measurement_device       'four circle diffractometer'
_diffrn_measurement_device_type  'Bruker AXS D8 Quest'
_diffrn_detector_type            
'PhotonIII_C14 charge-integrating and photon counting pixel array'
_diffrn_measurement_method       'omega and phi scans'
_diffrn_detector_area_resol_mean 7.4074
_diffrn_reflns_number            61585
_diffrn_reflns_av_unetI/netI     0.0404
_diffrn_reflns_av_R_equivalents  0.0753
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -48
_diffrn_reflns_limit_l_max       49
_diffrn_reflns_theta_min         2.267
_diffrn_reflns_theta_max         80.863
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             5252
_reflns_number_gt                4577
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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.
;

_computing_data_collection       'Apex4 v2022.10-0 (Bruker, 2022)'
_computing_cell_refinement       'SAINT V8.40B (Bruker, 2020)'
_computing_data_reduction        'SAINT V8.40B (Bruker, 2020)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015b)'
_computing_structure_refinement  
;  
SHELXL-2018/3 (Sheldrick, 2015a, 2018), 
SHELXLE Rev1460 (Hübschle et al., 2011)
;
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0728P)²+2.5786P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_extinction_coef       0.00031(9)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         5252
_refine_ls_number_parameters     281
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0467
_refine_ls_R_factor_gt           0.0412
_refine_ls_wR_factor_ref         0.1297
_refine_ls_wR_factor_gt          0.1249
_refine_ls_goodness_of_fit_ref   1.064
_refine_ls_restrained_S_all      1.064
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_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
Cl1 Cl 0.28736(5) 0.39858(5) 0.65957(2) 0.03657(15) Uani 1 1 d . . . . .
Cl2 Cl 0.38131(4) 0.13922(5) 0.70712(2) 0.03285(15) Uani 1 1 d . . . . .
Cl3 Cl 0.15647(5) 0.24541(5) 0.70766(2) 0.03450(15) Uani 1 1 d . . . . .
S1 S 0.48709(5) 0.08262(5) 0.56841(2) 0.03484(15) Uani 1 1 d . . . . .
O1 O 0.66370(17) 0.2685(2) 0.62677(4) 0.0521(5) Uani 1 1 d . . . . .
O2 O 0.37414(14) 0.12703(19) 0.55599(5) 0.0496(5) Uani 1 1 d . . . . .
O3 O 0.49618(18) -0.04820(18) 0.56934(6) 0.0537(5) Uani 1 1 d . . . . .
N1 N 0.51945(17) 0.14351(19) 0.60459(5) 0.0390(4) Uani 1 1 d . . . . .
N2 N 0.36525(16) 0.48654(17) 0.62852(5) 0.0331(4) Uani 1 1 d . . . . .
N3 N 0.52262(15) 0.06602(15) 0.70573(4) 0.0284(4) Uani 1 1 d . . . . .
C1 C 0.61814(19) 0.2129(2) 0.60242(5) 0.0357(5) Uani 1 1 d . . . . .
C2 C 0.66867(19) 0.2185(2) 0.56675(5) 0.0332(4) Uani 1 1 d . . . . .
C3 C 0.7640(2) 0.2860(2) 0.55530(6) 0.0429(5) Uani 1 1 d . . . . .
H3 H 0.809029 0.334874 0.570601 0.051 Uiso 1 1 calc R U . . .
C4 C 0.7917(2) 0.2799(3) 0.52068(7) 0.0520(6) Uani 1 1 d . . . . .
H4 H 0.856323 0.326121 0.512060 0.062 Uiso 1 1 calc R U . . .
C5 C 0.7270(3) 0.2077(3) 0.49851(7) 0.0534(7) Uani 1 1 d . . . . .
H5 H 0.748769 0.204753 0.474986 0.064 Uiso 1 1 calc R U . . .
C6 C 0.6306(2) 0.1391(3) 0.50972(6) 0.0463(6) Uani 1 1 d . . . . .
H6 H 0.585768 0.089762 0.494473 0.056 Uiso 1 1 calc R U . . .
C7 C 0.60373(19) 0.1468(2) 0.54438(5) 0.0333(4) Uani 1 1 d . . . . .
C8 C 0.3079(2) 0.6093(2) 0.62562(6) 0.0354(5) Uani 1 1 d . . . . .
H8A H 0.307433 0.650386 0.648234 0.042 Uiso 1 1 calc R U . . .
H8B H 0.224895 0.600624 0.617713 0.042 Uiso 1 1 calc R U . . .
C9 C 0.3798(2) 0.6846(2) 0.59960(7) 0.0462(6) Uani 1 1 d . . . . .
H9A H 0.326591 0.713863 0.581149 0.055 Uiso 1 1 calc R U . . .
H9B H 0.414108 0.756608 0.611211 0.055 Uiso 1 1 calc R U . . .
C10 C 0.4785(2) 0.6087(3) 0.58409(7) 0.0463(6) Uani 1 1 d . . . . .
H10 H 0.522578 0.657318 0.566547 0.056 Uiso 1 1 calc R U . . .
C11 C 0.4922(2) 0.5004(3) 0.64055(7) 0.0462(6) Uani 1 1 d . . . . .
H11A H 0.527666 0.419239 0.644673 0.055 Uiso 1 1 calc R U . . .
H11B H 0.494522 0.546936 0.662291 0.055 Uiso 1 1 calc R U . . .
C12 C 0.5626(2) 0.5683(3) 0.61256(8) 0.0569(7) Uani 1 1 d . . . . .
H12A H 0.602234 0.640313 0.622653 0.068 Uiso 1 1 calc R U . . .
H12B H 0.624328 0.514040 0.602982 0.068 Uiso 1 1 calc R U . . .
C13 C 0.3580(2) 0.4210(2) 0.59456(6) 0.0397(5) Uani 1 1 d . . . . .
H13A H 0.274026 0.410693 0.587794 0.048 Uiso 1 1 calc R U . . .
H13B H 0.394340 0.339242 0.596598 0.048 Uiso 1 1 calc R U . . .
C14 C 0.4236(3) 0.4954(3) 0.56741(7) 0.0522(6) Uani 1 1 d . . . . .
H14A H 0.367747 0.520333 0.549129 0.063 Uiso 1 1 calc R U . . .
H14B H 0.486717 0.445173 0.556854 0.063 Uiso 1 1 calc R U . . .
C15 C 0.61752(19) 0.1612(2) 0.70267(6) 0.0342(5) Uani 1 1 d . . . . .
H15A H 0.613556 0.217598 0.722441 0.041 Uiso 1 1 calc R U . . .
H15B H 0.605969 0.208923 0.681387 0.041 Uiso 1 1 calc R U . . .
C16 C 0.7382(2) 0.0976(2) 0.70187(8) 0.0468(6) Uani 1 1 d . . . . .
H16A H 0.781107 0.120641 0.680687 0.056 Uiso 1 1 calc R U . . .
H16B H 0.786115 0.124143 0.721782 0.056 Uiso 1 1 calc R U . . .
C17 C 0.7219(2) -0.0393(2) 0.70296(7) 0.0462(6) Uani 1 1 d . . . . .
H17 H 0.800604 -0.081001 0.701942 0.055 Uiso 1 1 calc R U . . .
C18 C 0.52423(19) -0.01719(19) 0.67486(5) 0.0324(4) Uani 1 1 d . . . . .
H18A H 0.508092 0.030117 0.653756 0.039 Uiso 1 1 calc R U . . .
H18B H 0.462244 -0.080458 0.677213 0.039 Uiso 1 1 calc R U . . .
C19 C 0.6462(3) -0.0766(3) 0.67260(10) 0.0685(10) Uani 1 1 d . . . . .
H19A H 0.637375 -0.166303 0.672281 0.082 Uiso 1 1 calc R U . . .
H19B H 0.685627 -0.051578 0.651027 0.082 Uiso 1 1 calc R U . . .
C20 C 0.5386(2) -0.00592(19) 0.73813(6) 0.0342(4) Uani 1 1 d . . . . .
H20A H 0.473491 -0.065745 0.740639 0.041 Uiso 1 1 calc R U . . .
H20B H 0.537322 0.049089 0.758247 0.041 Uiso 1 1 calc R U . . .
C21 C 0.6582(2) -0.0720(3) 0.73601(9) 0.0599(8) Uani 1 1 d . . . . .
H21A H 0.708007 -0.048760 0.755875 0.072 Uiso 1 1 calc R U . . .
H21B H 0.645200 -0.161096 0.736928 0.072 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cl1 N2 1.7807(19) . ?
Cl2 N3 1.7861(18) . ?
S1 O3 1.441(2) . ?
S1 O2 1.4477(17) . ?
S1 N1 1.603(2) . ?
S1 C7 1.762(2) . ?
O1 C1 1.240(3) . ?
N1 C1 1.352(3) . ?
N2 C8 1.500(3) . ?
N2 C13 1.509(3) . ?
N2 C11 1.514(3) . ?
N3 C20 1.500(3) . ?
N3 C15 1.501(3) . ?
N3 C18 1.511(3) . ?
C1 C2 1.504(3) . ?
C2 C3 1.380(3) . ?
C2 C7 1.385(3) . ?
C3 C4 1.387(4) . ?
C3 H3 0.9500 . ?
C4 C5 1.381(4) . ?
C4 H4 0.9500 . ?
C5 C6 1.393(4) . ?
C5 H5 0.9500 . ?
C6 C7 1.387(3) . ?
C6 H6 0.9500 . ?
C8 C9 1.540(3) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 C10 1.517(4) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 C12 1.525(4) . ?
C10 C14 1.534(4) . ?
C10 H10 1.0000 . ?
C11 C12 1.542(4) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 C14 1.528(3) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C15 C16 1.530(3) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C16 C17 1.516(4) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C17 C19 1.516(4) . ?
C17 C21 1.518(4) . ?
C17 H17 1.0000 . ?
C18 C19 1.526(3) . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
C20 C21 1.535(4) . ?
C20 H20A 0.9900 . ?
C20 H20B 0.9900 . ?
C21 H21A 0.9900 . ?
C21 H21B 0.9900 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O3 S1 O2 114.02(12) . . ?
O3 S1 N1 112.18(12) . . ?
O2 S1 N1 110.74(11) . . ?
O3 S1 C7 111.04(11) . . ?
O2 S1 C7 110.16(11) . . ?
N1 S1 C7 97.52(10) . . ?
C1 N1 S1 111.56(15) . . ?
C8 N2 C13 109.85(17) . . ?
C8 N2 C11 109.94(18) . . ?
C13 N2 C11 111.76(19) . . ?
C8 N2 Cl1 109.02(14) . . ?
C13 N2 Cl1 108.11(14) . . ?
C11 N2 Cl1 108.08(15) . . ?
C20 N3 C15 110.37(16) . . ?
C20 N3 C18 110.51(16) . . ?
C15 N3 C18 110.43(16) . . ?
C20 N3 Cl2 108.57(13) . . ?
C15 N3 Cl2 109.00(13) . . ?
C18 N3 Cl2 107.88(13) . . ?
O1 C1 N1 124.8(2) . . ?
O1 C1 C2 122.0(2) . . ?
N1 C1 C2 113.16(19) . . ?
C3 C2 C7 120.9(2) . . ?
C3 C2 C1 128.0(2) . . ?
C7 C2 C1 110.99(19) . . ?
C2 C3 C4 117.7(2) . . ?
C2 C3 H3 121.2 . . ?
C4 C3 H3 121.2 . . ?
C5 C4 C3 121.1(2) . . ?
C5 C4 H4 119.4 . . ?
C3 C4 H4 119.4 . . ?
C4 C5 C6 121.8(2) . . ?
C4 C5 H5 119.1 . . ?
C6 C5 H5 119.1 . . ?
C7 C6 C5 116.3(2) . . ?
C7 C6 H6 121.8 . . ?
C5 C6 H6 121.8 . . ?
C2 C7 C6 122.2(2) . . ?
C2 C7 S1 106.73(15) . . ?
C6 C7 S1 131.04(19) . . ?
N2 C8 C9 107.75(18) . . ?
N2 C8 H8A 110.2 . . ?
C9 C8 H8A 110.2 . . ?
N2 C8 H8B 110.2 . . ?
C9 C8 H8B 110.2 . . ?
H8A C8 H8B 108.5 . . ?
C10 C9 C8 110.7(2) . . ?
C10 C9 H9A 109.5 . . ?
C8 C9 H9A 109.5 . . ?
C10 C9 H9B 109.5 . . ?
C8 C9 H9B 109.5 . . ?
H9A C9 H9B 108.1 . . ?
C9 C10 C12 109.0(2) . . ?
C9 C10 C14 108.6(2) . . ?
C12 C10 C14 108.9(2) . . ?
C9 C10 H10 110.1 . . ?
C12 C10 H10 110.1 . . ?
C14 C10 H10 110.1 . . ?
N2 C11 C12 108.4(2) . . ?
N2 C11 H11A 110.0 . . ?
C12 C11 H11A 110.0 . . ?
N2 C11 H11B 110.0 . . ?
C12 C11 H11B 110.0 . . ?
H11A C11 H11B 108.4 . . ?
C10 C12 C11 109.6(2) . . ?
C10 C12 H12A 109.8 . . ?
C11 C12 H12A 109.8 . . ?
C10 C12 H12B 109.8 . . ?
C11 C12 H12B 109.8 . . ?
H12A C12 H12B 108.2 . . ?
N2 C13 C14 109.04(19) . . ?
N2 C13 H13A 109.9 . . ?
C14 C13 H13A 109.9 . . ?
N2 C13 H13B 109.9 . . ?
C14 C13 H13B 109.9 . . ?
H13A C13 H13B 108.3 . . ?
C13 C14 C10 109.6(2) . . ?
C13 C14 H14A 109.8 . . ?
C10 C14 H14A 109.8 . . ?
C13 C14 H14B 109.8 . . ?
C10 C14 H14B 109.8 . . ?
H14A C14 H14B 108.2 . . ?
N3 C15 C16 108.58(18) . . ?
N3 C15 H15A 110.0 . . ?
C16 C15 H15A 110.0 . . ?
N3 C15 H15B 110.0 . . ?
C16 C15 H15B 110.0 . . ?
H15A C15 H15B 108.4 . . ?
C17 C16 C15 110.1(2) . . ?
C17 C16 H16A 109.6 . . ?
C15 C16 H16A 109.6 . . ?
C17 C16 H16B 109.6 . . ?
C15 C16 H16B 109.6 . . ?
H16A C16 H16B 108.1 . . ?
C19 C17 C16 108.3(2) . . ?
C19 C17 C21 109.4(3) . . ?
C16 C17 C21 108.4(2) . . ?
C19 C17 H17 110.2 . . ?
C16 C17 H17 110.2 . . ?
C21 C17 H17 110.2 . . ?
N3 C18 C19 108.40(19) . . ?
N3 C18 H18A 110.0 . . ?
C19 C18 H18A 110.0 . . ?
N3 C18 H18B 110.0 . . ?
C19 C18 H18B 110.0 . . ?
H18A C18 H18B 108.4 . . ?
C17 C19 C18 110.3(2) . . ?
C17 C19 H19A 109.6 . . ?
C18 C19 H19A 109.6 . . ?
C17 C19 H19B 109.6 . . ?
C18 C19 H19B 109.6 . . ?
H19A C19 H19B 108.1 . . ?
N3 C20 C21 108.00(19) . . ?
N3 C20 H20A 110.1 . . ?
C21 C20 H20A 110.1 . . ?
N3 C20 H20B 110.1 . . ?
C21 C20 H20B 110.1 . . ?
H20A C20 H20B 108.4 . . ?
C17 C21 C20 110.5(2) . . ?
C17 C21 H21A 109.6 . . ?
C20 C21 H21A 109.6 . . ?
C17 C21 H21B 109.6 . . ?
C20 C21 H21B 109.6 . . ?
H21A C21 H21B 108.1 . . ?

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
O3 S1 N1 C1 115.17(17) . . . . ?
O2 S1 N1 C1 -116.19(17) . . . . ?
C7 S1 N1 C1 -1.24(18) . . . . ?
S1 N1 C1 O1 -178.7(2) . . . . ?
S1 N1 C1 C2 2.1(2) . . . . ?
O1 C1 C2 C3 -3.2(4) . . . . ?
N1 C1 C2 C3 176.0(2) . . . . ?
O1 C1 C2 C7 178.6(2) . . . . ?
N1 C1 C2 C7 -2.1(3) . . . . ?
C7 C2 C3 C4 0.4(4) . . . . ?
C1 C2 C3 C4 -177.6(2) . . . . ?
C2 C3 C4 C5 -0.7(4) . . . . ?
C3 C4 C5 C6 0.7(5) . . . . ?
C4 C5 C6 C7 -0.3(4) . . . . ?
C3 C2 C7 C6 -0.1(4) . . . . ?
C1 C2 C7 C6 178.3(2) . . . . ?
C3 C2 C7 S1 -177.17(19) . . . . ?
C1 C2 C7 S1 1.2(2) . . . . ?
C5 C6 C7 C2 0.0(4) . . . . ?
C5 C6 C7 S1 176.4(2) . . . . ?
O3 S1 C7 C2 -117.33(17) . . . . ?
O2 S1 C7 C2 115.38(17) . . . . ?
N1 S1 C7 C2 -0.03(17) . . . . ?
O3 S1 C7 C6 65.9(3) . . . . ?
O2 S1 C7 C6 -61.4(3) . . . . ?
N1 S1 C7 C6 -176.8(2) . . . . ?
C13 N2 C8 C9 -63.7(2) . . . . ?
C11 N2 C8 C9 59.7(2) . . . . ?
Cl1 N2 C8 C9 178.00(16) . . . . ?
N2 C8 C9 C10 3.5(3) . . . . ?
C8 C9 C10 C12 -61.4(3) . . . . ?
C8 C9 C10 C14 57.1(3) . . . . ?
C8 N2 C11 C12 -65.2(3) . . . . ?
C13 N2 C11 C12 57.0(3) . . . . ?
Cl1 N2 C11 C12 175.9(2) . . . . ?
C9 C10 C12 C11 55.6(3) . . . . ?
C14 C10 C12 C11 -62.7(3) . . . . ?
N2 C11 C12 C10 5.3(3) . . . . ?
C8 N2 C13 C14 60.7(3) . . . . ?
C11 N2 C13 C14 -61.6(3) . . . . ?
Cl1 N2 C13 C14 179.60(18) . . . . ?
N2 C13 C14 C10 2.2(3) . . . . ?
C9 C10 C14 C13 -60.2(3) . . . . ?
C12 C10 C14 C13 58.4(3) . . . . ?
C20 N3 C15 C16 60.3(2) . . . . ?
C18 N3 C15 C16 -62.2(2) . . . . ?
Cl2 N3 C15 C16 179.44(16) . . . . ?
N3 C15 C16 C17 2.3(3) . . . . ?
C15 C16 C17 C19 58.2(3) . . . . ?
C15 C16 C17 C21 -60.5(3) . . . . ?
C20 N3 C18 C19 -63.6(3) . . . . ?
C15 N3 C18 C19 58.8(3) . . . . ?
Cl2 N3 C18 C19 177.8(2) . . . . ?
C16 C17 C19 C18 -61.7(4) . . . . ?
C21 C17 C19 C18 56.4(4) . . . . ?
N3 C18 C19 C17 3.6(4) . . . . ?
C15 N3 C20 C21 -62.6(2) . . . . ?
C18 N3 C20 C21 59.8(2) . . . . ?
Cl2 N3 C20 C21 177.96(18) . . . . ?
C19 C17 C21 C20 -60.0(3) . . . . ?
C16 C17 C21 C20 58.0(3) . . . . ?
N3 C20 C21 C17 2.1(3) . . . . ?

_refine_diff_density_max         0.393
_refine_diff_density_min         -0.658
_refine_diff_density_rms         0.065



####################################################################### 
# 
# 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_RS243a_0m
_database_code_depnum_ccdc_archive 'CCDC 2384419'
loop_
_audit_author_name
_audit_author_address
'Matthias Zeller '
;Purdue University  
United States of America
;
_audit_update_record             
;
2024-09-16 deposited with the CCDC.	2024-11-19 downloaded from the CCDC.
;

# start Validation Reply Form
_vrf_PLAT431_RS243a_0m           
;
PROBLEM: Short Inter HL..A Contact  Cl1_1    ..O1_2     .       2.75 Ang.  
RESPONSE: Halogen bond.
;
# end Validation Reply Form


_audit_creation_method           SHELXL-2019/3
_shelx_SHELXL_version_number     2019/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C7 H4 Cl N O3 S'
_chemical_formula_weight         217.62

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_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.
;

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

_cell_length_a                   8.4794(5)
_cell_length_b                   28.3380(18)
_cell_length_c                   7.7102(5)
_cell_angle_alpha                90
_cell_angle_beta                 116.892(2)
_cell_angle_gamma                90
_cell_volume                     1652.33(18)
_cell_formula_units_Z            8
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    9737
_cell_measurement_theta_min      2.8752
_cell_measurement_theta_max      33.1586

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.750
_exptl_crystal_F_000             880
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.320
_exptl_crystal_size_mid          0.190
_exptl_crystal_size_min          0.160
_exptl_absorpt_coefficient_mu    0.683
_shelx_estimated_absorpt_T_min   0.811
_shelx_estimated_absorpt_T_max   0.899
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6632
_exptl_absorpt_correction_T_max  0.7465
_exptl_absorpt_process_details   
;
 SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
 J. Appl. Cryst. 48 (2015) 3-10
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine focus sealed tube X-ray source'
_diffrn_source_current           '30 mA'
_diffrn_source_voltage           '50 kV'
_diffrn_radiation_monochromator  'Triumph curved graphite crystal'
_diffrn_measurement_device       'three circle diffractometer'
_diffrn_measurement_device_type  'Bruker AXS D8 Quest'
_diffrn_detector_type            
'PhotonII charge-integrating pixel array (CPAD)'
_diffrn_measurement_method       'omega and phi scans'
_diffrn_detector_area_resol_mean 7.4074
_diffrn_reflns_number            49424
_diffrn_reflns_av_unetI/netI     0.0151
_diffrn_reflns_av_R_equivalents  0.0257
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -43
_diffrn_reflns_limit_k_max       43
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         2.693
_diffrn_reflns_theta_max         33.161
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             6276
_reflns_number_gt                5879
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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.
;

_computing_data_collection       'Apex5 v2023.9-2 (Bruker, 2023)'
_computing_cell_refinement       'SAINT V8.40B (Bruker, 2020)'
_computing_data_reduction        'SAINT V8.40B (Bruker, 2020)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015b)'
_computing_structure_refinement  
;  
SHELXL-2019/2 (Sheldrick, 2015a, 2019), 
SHELXLE Rev1613 (Hübschle et al., 2011)
;
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0338P)²+0.7543P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2019/2 (Sheldrick 2019)'
_refine_ls_extinction_coef       0.0018(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         6276
_refine_ls_number_parameters     236
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0312
_refine_ls_R_factor_gt           0.0284
_refine_ls_wR_factor_ref         0.0783
_refine_ls_wR_factor_gt          0.0772
_refine_ls_goodness_of_fit_ref   1.124
_refine_ls_restrained_S_all      1.124
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_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
Cl1_1 Cl 0.63141(3) 0.84784(2) 0.39466(4) 0.02437(6) Uani 1 1 d . . . . .
S1_1 S 0.97226(3) 0.84352(2) 0.73942(4) 0.01685(6) Uani 1 1 d . . . . .
O1_1 O 0.69005(11) 0.74332(3) 0.43115(13) 0.02735(18) Uani 1 1 d . . . . .
O2_1 O 0.93990(12) 0.86745(3) 0.88267(13) 0.02588(17) Uani 1 1 d . . . . .
O3_1 O 1.04384(12) 0.87003(3) 0.63377(13) 0.02517(17) Uani 1 1 d . . . . .
N1_1 N 0.78391(12) 0.81573(3) 0.57905(14) 0.02153(17) Uani 1 1 d . . . . .
C1_1 C 0.79970(13) 0.76712(4) 0.55849(15) 0.01830(17) Uani 1 1 d . . . . .
C2_1 C 0.97214(13) 0.75202(3) 0.71693(14) 0.01647(16) Uani 1 1 d . . . . .
C3_1 C 1.07890(13) 0.78933(3) 0.82261(14) 0.01616(16) Uani 1 1 d . . . . .
C4_1 C 1.24701(14) 0.78287(4) 0.97346(15) 0.02051(18) Uani 1 1 d . . . . .
H4_1 H 1.317673 0.808749 1.045120 0.025 Uiso 1 1 calc R U . . .
C5_1 C 1.30724(14) 0.73651(4) 1.01480(17) 0.0234(2) Uani 1 1 d . . . . .
H5_1 H 1.422553 0.730571 1.115901 0.028 Uiso 1 1 calc R U . . .
C6_1 C 1.20201(15) 0.69868(4) 0.91107(17) 0.0234(2) Uani 1 1 d . . . . .
H6_1 H 1.246503 0.667443 0.943018 0.028 Uiso 1 1 calc R U . . .
C7_1 C 1.03196(14) 0.70596(4) 0.76070(16) 0.02057(19) Uani 1 1 d . . . . .
H7_1 H 0.959696 0.680144 0.690729 0.025 Uiso 1 1 calc R U . . .
C1_2 C 0.37429(13) 0.58090(4) 0.44390(15) 0.01782(17) Uani 1 1 d . . . . .
Cl1_2 Cl 0.55299(4) 0.64591(2) 0.35195(4) 0.02434(6) Uani 1 1 d . . . . .
S1_2 S 0.40908(4) 0.55838(2) 0.13109(4) 0.01908(6) Uani 1 1 d . . . . .
O1_2 O 0.38241(12) 0.60397(3) 0.57963(12) 0.02469(16) Uani 1 1 d . . . . .
O2_2 O 0.29053(13) 0.58083(4) -0.04538(14) 0.03022(19) Uani 1 1 d . . . . .
O3_2 O 0.57515(12) 0.54198(3) 0.14982(14) 0.02687(17) Uani 1 1 d . . . . .
N1_2 N 0.44766(15) 0.59426(3) 0.32315(16) 0.02532(19) Uani 1 1 d . . . . .
C2_2 C 0.28965(13) 0.53436(4) 0.37584(15) 0.01729(17) Uani 1 1 d . . . . .
C3_2 C 0.30022(14) 0.51758(4) 0.21145(15) 0.01784(17) Uani 1 1 d . . . . .
C4_2 C 0.22938(16) 0.47457(4) 0.12731(17) 0.0231(2) Uani 1 1 d . . . . .
H4_2 H 0.236870 0.463512 0.014954 0.028 Uiso 1 1 calc R U . . .
C5_2 C 0.14634(16) 0.44821(4) 0.21554(19) 0.0253(2) Uani 1 1 d . . . . .
H5_2 H 0.095416 0.418581 0.161465 0.030 Uiso 1 1 calc R U . . .
C6_2 C 0.13644(16) 0.46432(4) 0.38066(19) 0.0250(2) Uani 1 1 d . . . . .
H6_2 H 0.080415 0.445378 0.438335 0.030 Uiso 1 1 calc R U . . .
C7_2 C 0.20774(15) 0.50795(4) 0.46287(17) 0.02162(19) Uani 1 1 d . . . . .
H7_2 H 0.200242 0.519158 0.575040 0.026 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cl1_1 N1_1 1.6906(9) . ?
S1_1 O2_1 1.4245(9) . ?
S1_1 O3_1 1.4294(9) . ?
S1_1 N1_1 1.7069(9) . ?
S1_1 C3_1 1.7501(10) . ?
O1_1 C1_1 1.2072(13) . ?
N1_1 C1_1 1.4000(14) . ?
C1_1 C2_1 1.4824(14) . ?
C2_1 C7_1 1.3858(14) . ?
C2_1 C3_1 1.3907(14) . ?
C3_1 C4_1 1.3850(14) . ?
C4_1 C5_1 1.3935(16) . ?
C4_1 H4_1 0.9500 . ?
C5_1 C6_1 1.3925(17) . ?
C5_1 H5_1 0.9500 . ?
C6_1 C7_1 1.3977(15) . ?
C6_1 H6_1 0.9500 . ?
C7_1 H7_1 0.9500 . ?
C1_2 O1_2 1.2092(13) . ?
C1_2 N1_2 1.3861(14) . ?
C1_2 C2_2 1.4795(14) . ?
Cl1_2 N1_2 1.6762(10) . ?
S1_2 O2_2 1.4246(9) . ?
S1_2 O3_2 1.4268(9) . ?
S1_2 N1_2 1.7017(10) . ?
S1_2 C3_2 1.7578(11) . ?
C2_2 C7_2 1.3836(15) . ?
C2_2 C3_2 1.3941(14) . ?
C3_2 C4_2 1.3837(15) . ?
C4_2 C5_2 1.3963(17) . ?
C4_2 H4_2 0.9500 . ?
C5_2 C6_2 1.3903(17) . ?
C5_2 H5_2 0.9500 . ?
C6_2 C7_2 1.3964(16) . ?
C6_2 H6_2 0.9500 . ?
C7_2 H7_2 0.9500 . ?

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_1 S1_1 O3_1 118.17(6) . . ?
O2_1 S1_1 N1_1 109.64(5) . . ?
O3_1 S1_1 N1_1 109.21(5) . . ?
O2_1 S1_1 C3_1 112.48(5) . . ?
O3_1 S1_1 C3_1 112.82(5) . . ?
N1_1 S1_1 C3_1 91.13(5) . . ?
C1_1 N1_1 Cl1_1 120.69(7) . . ?
C1_1 N1_1 S1_1 115.46(7) . . ?
Cl1_1 N1_1 S1_1 118.03(6) . . ?
O1_1 C1_1 N1_1 124.32(10) . . ?
O1_1 C1_1 C2_1 128.22(10) . . ?
N1_1 C1_1 C2_1 107.45(8) . . ?
C7_1 C2_1 C3_1 120.26(9) . . ?
C7_1 C2_1 C1_1 126.06(9) . . ?
C3_1 C2_1 C1_1 113.67(9) . . ?
C4_1 C3_1 C2_1 122.79(9) . . ?
C4_1 C3_1 S1_1 126.06(8) . . ?
C2_1 C3_1 S1_1 111.15(7) . . ?
C3_1 C4_1 C5_1 116.63(10) . . ?
C3_1 C4_1 H4_1 121.7 . . ?
C5_1 C4_1 H4_1 121.7 . . ?
C6_1 C5_1 C4_1 121.41(10) . . ?
C6_1 C5_1 H5_1 119.3 . . ?
C4_1 C5_1 H5_1 119.3 . . ?
C5_1 C6_1 C7_1 121.03(10) . . ?
C5_1 C6_1 H6_1 119.5 . . ?
C7_1 C6_1 H6_1 119.5 . . ?
C2_1 C7_1 C6_1 117.88(10) . . ?
C2_1 C7_1 H7_1 121.1 . . ?
C6_1 C7_1 H7_1 121.1 . . ?
O1_2 C1_2 N1_2 124.50(10) . . ?
O1_2 C1_2 C2_2 128.13(10) . . ?
N1_2 C1_2 C2_2 107.36(9) . . ?
O2_2 S1_2 O3_2 118.67(6) . . ?
O2_2 S1_2 N1_2 109.82(6) . . ?
O3_2 S1_2 N1_2 108.30(6) . . ?
O2_2 S1_2 C3_2 111.98(5) . . ?
O3_2 S1_2 C3_2 113.69(5) . . ?
N1_2 S1_2 C3_2 90.65(5) . . ?
C1_2 N1_2 Cl1_2 121.58(8) . . ?
C1_2 N1_2 S1_2 116.95(7) . . ?
Cl1_2 N1_2 S1_2 121.22(6) . . ?
C7_2 C2_2 C3_2 120.61(10) . . ?
C7_2 C2_2 C1_2 125.42(10) . . ?
C3_2 C2_2 C1_2 113.96(9) . . ?
C4_2 C3_2 C2_2 122.27(10) . . ?
C4_2 C3_2 S1_2 126.86(8) . . ?
C2_2 C3_2 S1_2 110.86(8) . . ?
C3_2 C4_2 C5_2 116.77(10) . . ?
C3_2 C4_2 H4_2 121.6 . . ?
C5_2 C4_2 H4_2 121.6 . . ?
C6_2 C5_2 C4_2 121.54(10) . . ?
C6_2 C5_2 H5_2 119.2 . . ?
C4_2 C5_2 H5_2 119.2 . . ?
C5_2 C6_2 C7_2 120.88(11) . . ?
C5_2 C6_2 H6_2 119.6 . . ?
C7_2 C6_2 H6_2 119.6 . . ?
C2_2 C7_2 C6_2 117.91(10) . . ?
C2_2 C7_2 H7_2 121.0 . . ?
C6_2 C7_2 H7_2 121.0 . . ?

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
O2_1 S1_1 N1_1 C1_1 -123.84(9) . . . . ?
O3_1 S1_1 N1_1 C1_1 105.23(9) . . . . ?
C3_1 S1_1 N1_1 C1_1 -9.45(9) . . . . ?
O2_1 S1_1 N1_1 Cl1_1 82.78(8) . . . . ?
O3_1 S1_1 N1_1 Cl1_1 -48.14(8) . . . . ?
C3_1 S1_1 N1_1 Cl1_1 -162.82(7) . . . . ?
Cl1_1 N1_1 C1_1 O1_1 -15.09(16) . . . . ?
S1_1 N1_1 C1_1 O1_1 -167.70(10) . . . . ?
Cl1_1 N1_1 C1_1 C2_1 164.21(8) . . . . ?
S1_1 N1_1 C1_1 C2_1 11.60(12) . . . . ?
O1_1 C1_1 C2_1 C7_1 -7.39(19) . . . . ?
N1_1 C1_1 C2_1 C7_1 173.34(11) . . . . ?
O1_1 C1_1 C2_1 C3_1 170.96(11) . . . . ?
N1_1 C1_1 C2_1 C3_1 -8.31(13) . . . . ?
C7_1 C2_1 C3_1 C4_1 0.18(16) . . . . ?
C1_1 C2_1 C3_1 C4_1 -178.28(10) . . . . ?
C7_1 C2_1 C3_1 S1_1 -179.68(8) . . . . ?
C1_1 C2_1 C3_1 S1_1 1.86(11) . . . . ?
O2_1 S1_1 C3_1 C4_1 -64.02(11) . . . . ?
O3_1 S1_1 C3_1 C4_1 72.73(11) . . . . ?
N1_1 S1_1 C3_1 C4_1 -175.85(10) . . . . ?
O2_1 S1_1 C3_1 C2_1 115.84(8) . . . . ?
O3_1 S1_1 C3_1 C2_1 -107.42(8) . . . . ?
N1_1 S1_1 C3_1 C2_1 4.01(8) . . . . ?
C2_1 C3_1 C4_1 C5_1 0.72(16) . . . . ?
S1_1 C3_1 C4_1 C5_1 -179.44(9) . . . . ?
C3_1 C4_1 C5_1 C6_1 -0.95(17) . . . . ?
C4_1 C5_1 C6_1 C7_1 0.30(18) . . . . ?
C3_1 C2_1 C7_1 C6_1 -0.85(16) . . . . ?
C1_1 C2_1 C7_1 C6_1 177.41(10) . . . . ?
C5_1 C6_1 C7_1 C2_1 0.61(17) . . . . ?
O1_2 C1_2 N1_2 Cl1_2 -1.67(17) . . . . ?
C2_2 C1_2 N1_2 Cl1_2 178.90(8) . . . . ?
O1_2 C1_2 N1_2 S1_2 -175.97(9) . . . . ?
C2_2 C1_2 N1_2 S1_2 4.61(12) . . . . ?
O2_2 S1_2 N1_2 C1_2 108.98(10) . . . . ?
O3_2 S1_2 N1_2 C1_2 -119.99(9) . . . . ?
C3_2 S1_2 N1_2 C1_2 -4.72(10) . . . . ?
O2_2 S1_2 N1_2 Cl1_2 -65.34(9) . . . . ?
O3_2 S1_2 N1_2 Cl1_2 65.69(9) . . . . ?
C3_2 S1_2 N1_2 Cl1_2 -179.03(8) . . . . ?
O1_2 C1_2 C2_2 C7_2 -2.22(18) . . . . ?
N1_2 C1_2 C2_2 C7_2 177.18(10) . . . . ?
O1_2 C1_2 C2_2 C3_2 178.67(11) . . . . ?
N1_2 C1_2 C2_2 C3_2 -1.94(12) . . . . ?
C7_2 C2_2 C3_2 C4_2 0.52(16) . . . . ?
C1_2 C2_2 C3_2 C4_2 179.68(10) . . . . ?
C7_2 C2_2 C3_2 S1_2 179.55(8) . . . . ?
C1_2 C2_2 C3_2 S1_2 -1.29(11) . . . . ?
O2_2 S1_2 C3_2 C4_2 70.47(11) . . . . ?
O3_2 S1_2 C3_2 C4_2 -67.44(12) . . . . ?
N1_2 S1_2 C3_2 C4_2 -177.80(11) . . . . ?
O2_2 S1_2 C3_2 C2_2 -108.50(9) . . . . ?
O3_2 S1_2 C3_2 C2_2 113.59(8) . . . . ?
N1_2 S1_2 C3_2 C2_2 3.23(8) . . . . ?
C2_2 C3_2 C4_2 C5_2 -0.26(17) . . . . ?
S1_2 C3_2 C4_2 C5_2 -179.13(9) . . . . ?
C3_2 C4_2 C5_2 C6_2 -0.40(18) . . . . ?
C4_2 C5_2 C6_2 C7_2 0.82(19) . . . . ?
C3_2 C2_2 C7_2 C6_2 -0.10(16) . . . . ?
C1_2 C2_2 C7_2 C6_2 -179.16(10) . . . . ?
C5_2 C6_2 C7_2 C2_2 -0.55(18) . . . . ?

_refine_diff_density_max         0.483
_refine_diff_density_min         -0.349
_refine_diff_density_rms         0.061



####################################################################### 
# 
# 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_RS213_0m
_database_code_depnum_ccdc_archive 'CCDC 2384418'
loop_
_audit_author_name
_audit_author_address
'Matthias Zeller '
;Purdue University  
United States of America
;
_audit_update_record             
;
2024-09-16 deposited with the CCDC.	2024-11-19 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2019/3
_shelx_SHELXL_version_number     2019/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         "'C7 H13 Cl N, Cl"
_chemical_formula_sum            'C7 H13 Cl2 N'
_chemical_formula_weight         182.08

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           36
_space_group_name_H-M_alt        'C m c 21'
_space_group_name_Hall           'C 2c -2'

_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.
;

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

_cell_length_a                   7.0792(8)
_cell_length_b                   10.8984(12)
_cell_length_c                   11.0370(13)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     851.53(17)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    2105
_cell_measurement_theta_min      7.4613
_cell_measurement_theta_max      80.5635

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.420
_exptl_crystal_F_000             384
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.210
_exptl_crystal_size_mid          0.190
_exptl_crystal_size_min          0.040
_exptl_absorpt_coefficient_mu    6.243
_shelx_estimated_absorpt_T_min   0.354
_shelx_estimated_absorpt_T_max   0.788
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5776
_exptl_absorpt_correction_T_max  0.7543
_exptl_absorpt_process_details   
;
 SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
 J. Appl. Cryst. 48 (2015) 3-10
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   'I-mu-S microsource X-ray tube'
_diffrn_source_current           '1.0 mA'
_diffrn_source_voltage           '50 kV'
_diffrn_radiation_monochromator  'laterally graded multilayer (Goebel) mirror'
_diffrn_measurement_device       'four circle diffractometer'
_diffrn_measurement_device_type  'Bruker AXS D8 Quest'
_diffrn_detector_type            
'PhotonIII_C14 charge-integrating and photon counting pixel array'
_diffrn_measurement_method       'omega and phi scans'
_diffrn_detector_area_resol_mean 7.4074
_diffrn_reflns_number            3151
_diffrn_reflns_av_unetI/netI     0.0487
_diffrn_reflns_av_R_equivalents  0.0452
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         7.461
_diffrn_reflns_theta_max         80.549
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.974
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.974
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.869
_diffrn_reflns_point_group_measured_fraction_full 0.918
_reflns_number_total             880
_reflns_number_gt                822
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.692
_reflns_Friedel_fraction_max     0.752
_reflns_Friedel_fraction_full    0.828

_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.
;

_computing_data_collection       'Apex4 v2022.10-0 (Bruker, 2022)'
_computing_cell_refinement       'SAINT V8.40B (Bruker, 2020)'
_computing_data_reduction        'SAINT V8.40B (Bruker, 2020)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015b)'
_computing_structure_refinement  
;  
SHELXL-2019/2 (Sheldrick, 2015a, 2019), 
SHELXLE Rev1506 (Hübschle et al., 2011)
;
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0303P)²+0.4417P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 305 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.03(2)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         880
_refine_ls_number_parameters     55
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0327
_refine_ls_R_factor_gt           0.0309
_refine_ls_wR_factor_ref         0.0798
_refine_ls_wR_factor_gt          0.0788
_refine_ls_goodness_of_fit_ref   1.136
_refine_ls_restrained_S_all      1.135
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_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
Cl1 Cl 0.500000 0.61389(10) 0.56163(7) 0.0241(3) Uani 1 2 d S T P . .
Cl2 Cl 0.500000 0.38702(11) 0.65156(9) 0.0277(4) Uani 1 2 d S T P . .
N1 N 0.500000 0.7630(3) 0.4907(4) 0.0217(8) Uani 1 2 d S T P . .
C1 C 0.3246(5) 0.7728(3) 0.4138(3) 0.0250(7) Uani 1 1 d . . . . .
H1A H 0.210746 0.764930 0.465295 0.030 Uiso 1 1 calc R U . . .
H1B H 0.322671 0.706011 0.352985 0.030 Uiso 1 1 calc R U . . .
C2 C 0.3246(5) 0.8980(3) 0.3497(6) 0.0371(8) Uani 1 1 d . . . . .
H2A H 0.324262 0.886056 0.260832 0.045 Uiso 1 1 calc R U . . .
H2B H 0.209695 0.944485 0.372205 0.045 Uiso 1 1 calc R U . . .
C3 C 0.500000 0.9698(4) 0.3873(5) 0.0320(12) Uani 1 2 d S T P . .
H3 H 0.500001 1.051882 0.346848 0.038 Uiso 1 2 calc R U P . .
C4 C 0.500000 0.9861(5) 0.5241(5) 0.0306(11) Uani 1 2 d S T P . .
H4A H 0.386771 1.033160 0.548937 0.037 Uiso 0.5 1 calc R U P . .
H4B H 0.613229 1.033160 0.548937 0.037 Uiso 0.5 1 calc R U P . .
C5 C 0.500000 0.8611(5) 0.5871(5) 0.0257(10) Uani 1 2 d S T P . .
H5A H 0.613437 0.852876 0.638973 0.031 Uiso 0.5 1 calc R U P . .
H5B H 0.386563 0.852876 0.638973 0.031 Uiso 0.5 1 calc R U P . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cl1 N1 1.804(4) . ?
N1 C1 1.508(4) 4_655 ?
N1 C1 1.508(4) . ?
N1 C5 1.509(6) . ?
C1 C2 1.537(5) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C2 C3 1.524(4) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 C4 1.521(7) . ?
C3 H3 1.0000 . ?
C4 C5 1.530(7) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 N1 C1 110.9(4) 4_655 . ?
C1 N1 C5 110.3(2) 4_655 . ?
C1 N1 C5 110.3(2) . . ?
C1 N1 Cl1 107.9(2) 4_655 . ?
C1 N1 Cl1 107.9(2) . . ?
C5 N1 Cl1 109.4(3) . . ?
N1 C1 C2 108.8(3) . . ?
N1 C1 H1A 109.9 . . ?
C2 C1 H1A 109.9 . . ?
N1 C1 H1B 109.9 . . ?
C2 C1 H1B 109.9 . . ?
H1A C1 H1B 108.3 . . ?
C3 C2 C1 109.3(3) . . ?
C3 C2 H2A 109.8 . . ?
C1 C2 H2A 109.8 . . ?
C3 C2 H2B 109.8 . . ?
C1 C2 H2B 109.8 . . ?
H2A C2 H2B 108.3 . . ?
C4 C3 C2 109.3(3) . . ?
C4 C3 C2 109.3(3) . 4_655 ?
C2 C3 C2 109.0(4) . 4_655 ?
C4 C3 H3 109.8 . . ?
C2 C3 H3 109.8 . . ?
C2 C3 H3 109.8 4_655 . ?
C3 C4 C5 110.3(4) . . ?
C3 C4 H4A 109.6 . . ?
C5 C4 H4A 109.6 . . ?
C3 C4 H4B 109.6 . . ?
C5 C4 H4B 109.6 . . ?
H4A C4 H4B 108.1 . . ?
N1 C5 C4 108.1(4) . . ?
N1 C5 H5A 110.1 . . ?
C4 C5 H5A 110.1 . . ?
N1 C5 H5B 110.1 . . ?
C4 C5 H5B 110.1 . . ?
H5A C5 H5B 108.4 . . ?

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
C1 N1 C1 C2 -60.5(5) 4_655 . . . ?
C5 N1 C1 C2 62.0(4) . . . . ?
Cl1 N1 C1 C2 -178.5(3) . . . . ?
N1 C1 C2 C3 -0.8(5) . . . . ?
C1 C2 C3 C4 -58.8(5) . . . . ?
C1 C2 C3 C2 60.6(7) . . . 4_655 ?
C2 C3 C4 C5 59.6(3) . . . . ?
C2 C3 C4 C5 -59.6(3) 4_655 . . . ?
C1 N1 C5 C4 61.4(2) 4_655 . . . ?
C1 N1 C5 C4 -61.4(2) . . . . ?
Cl1 N1 C5 C4 180.000(2) . . . . ?
C3 C4 C5 N1 0.000(2) . . . . ?

_refine_diff_density_max         0.294
_refine_diff_density_min         -0.243
_refine_diff_density_rms         0.060



