# Electronic Supplementary Material (ESI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 2023

####################################################################### 
# 
# 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_hkl_a
_audit_block_doi                 10.5517/ccdc.csd.cc2cmsjb
_database_code_depnum_ccdc_archive 'CCDC 2193762'
loop_
_audit_author_name
_audit_author_address
'Khalil A Abboud'
;University of Florida
United States of America
;

_audit_update_record             
;
2022-07-30 deposited with the CCDC.	2023-02-13 downloaded from the CCDC.
;
_publcif_datablock.id            {e007c1c8-273a-4d2f-a8c1-4d929db8c2cb}

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C27 H24 F3 N3 O2 S'
_chemical_formula_weight         511.55

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'
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'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'

_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'

_cell_length_a                   7.4828(3)
_cell_length_b                   18.3087(7)
_cell_length_c                   18.4701(7)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2530.41(17)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    9942
_cell_measurement_theta_min      2.21
_cell_measurement_theta_max      29.60

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless

_exptl_crystal_density_meas      .

_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.343
_exptl_crystal_F_000             1064

_exptl_transmission_factor_min   0.6706
_exptl_transmission_factor_max   0.7464

_exptl_crystal_size_max          0.352
_exptl_crystal_size_mid          0.198
_exptl_crystal_size_min          0.128
_exptl_absorpt_coefficient_mu    0.180
_shelx_estimated_absorpt_T_min   0.939
_shelx_estimated_absorpt_T_max   0.977

_exptl_absorpt_correction_type   multi-scan

_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?

_exptl_absorpt_process_details   
'Sheldrick, G. M., sadabs (2015). Acta Cryst. C71, 3-8.'

_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'micro source 3.0'
_diffrn_measurement_device_type  'D8 Venture with PHOTON III'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?

_diffrn_reflns_number            43297
_diffrn_reflns_av_unetI/netI     0.0235
_diffrn_reflns_av_R_equivalents  0.0301
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_theta_min         2.205
_diffrn_reflns_theta_max         32.461
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.934
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.934
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.911
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             8307
_reflns_number_gt                6880
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.747
_reflns_Friedel_fraction_max     0.882
_reflns_Friedel_fraction_full    0.997

_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       'Bruker APEX3 (Bruker, 2019)'
_computing_cell_refinement       'Bruker APEX3 (Bruker, 2019)'
_computing_data_reduction        'Bruker Apex3 SAINT (Bruker, 2019)'
_computing_structure_solution    'SHELXL2015, Sheldrick G. M. 2019'
_computing_structure_refinement  'SHELXL2015, Sheldrick G. M. 2019'
_computing_molecular_graphics    'XP in SHELXTL-plus, Bruker 2019'
_computing_publication_material  'SHELXL2015, Sheldrick, G. M. 2019'

_refine_special_details          
;
All H atoms were positioned geometrically ( C---H = 0.93/1.00 Å) and   
allowed to ride with Uiso(H)= 1.2/1.5Ueq(C).
Methyl ones were allowed to rotate around the corresponding C---C.

 The molecule has three disordered groups; SO2, CN and the F atoms.  
Two parts are refined in each case with their site occupation parameters
 fixed after being fully refined.  
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0616P)²+0.1908P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_primary     direct
_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 2685 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   -0.004(15)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         8307
_refine_ls_number_parameters     393
_refine_ls_number_restraints     804
_refine_ls_R_factor_all          0.0491
_refine_ls_R_factor_gt           0.0370
_refine_ls_wR_factor_ref         0.1096
_refine_ls_wR_factor_gt          0.1009
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_restrained_S_all      1.000
_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
F1 F 0.782(3) 0.3303(13) 0.1471(11) 0.076(2) Uani 0.55 1 d D U P A 1
F2 F 0.451(3) 0.2854(7) 0.1204(9) 0.127(5) Uani 0.55 1 d D U P B 1
F3 F 0.1654(16) 0.3547(10) 0.1837(10) 0.118(5) Uani 0.55 1 d D U P C 1
F1' F 0.776(4) 0.3199(15) 0.1596(14) 0.093(5) Uani 0.45 1 d D U P A 2
F2' F 0.437(2) 0.2810(6) 0.1273(9) 0.084(3) Uani 0.45 1 d D U P B 2
F3' F 0.1676(19) 0.3702(12) 0.1663(12) 0.098(4) Uani 0.45 1 d D U P C 2
N1 N 0.42429(19) 0.50552(8) 0.44237(8) 0.0388(3) Uani 1 1 d D U . . .
C1 C 0.5034(3) 0.55357(10) 0.49832(11) 0.0441(4) Uani 1 1 d . U . . .
H1A H 0.411461 0.571294 0.533490 0.053 Uiso 1 1 calc R U . . .
C2 C 0.5871(3) 0.61641(9) 0.45584(12) 0.0459(4) Uani 1 1 d . U . . .
H2A H 0.492271 0.643570 0.429917 0.055 Uiso 1 1 calc R U . . .
H2B H 0.646139 0.650544 0.489843 0.055 Uiso 1 1 calc R U . . .
C3 C 0.7217(2) 0.58861(9) 0.40230(10) 0.0379(3) Uani 1 1 d . U . . .
C4 C 0.6792(2) 0.51895(8) 0.36152(9) 0.0356(3) Uani 1 1 d . U . . .
H4A H 0.794074 0.495754 0.346172 0.043 Uiso 1 1 calc R U . . .
C5 C 0.5800(2) 0.46571(9) 0.41265(9) 0.0356(3) Uani 1 1 d . U . . .
H5A H 0.541472 0.420690 0.386260 0.043 Uiso 1 1 calc R U . . .
C6 C 0.6923(2) 0.44632(10) 0.47983(10) 0.0409(4) Uani 1 1 d . U . . .
H6A H 0.659899 0.397378 0.498473 0.049 Uiso 1 1 calc R U . . .
H6B H 0.821416 0.446858 0.468188 0.049 Uiso 1 1 calc R U . . .
C7 C 0.6465(3) 0.50597(11) 0.53553(11) 0.0470(4) Uani 1 1 d . U . . .
H7A H 0.753600 0.535345 0.547482 0.056 Uiso 1 1 calc R U . . .
H7B H 0.599057 0.484061 0.580607 0.056 Uiso 1 1 calc R U . . .
C8 C 0.8753(3) 0.62551(11) 0.39148(12) 0.0456(4) Uani 1 1 d . U . . .
C9 C 0.927(3) 0.6832(7) 0.4289(12) 0.061(3) Uani 0.5 1 d D U P D 1
N2 N 0.973(2) 0.7371(8) 0.4522(11) 0.097(5) Uani 0.5 1 d D U P D 1
C10 C 1.003(2) 0.5972(12) 0.3322(11) 0.050(3) Uani 0.5 1 d D U P D 1
N3 N 1.101(3) 0.5790(12) 0.2885(11) 0.070(4) Uani 0.5 1 d D U P D 1
C9' C 0.905(2) 0.6991(6) 0.4298(10) 0.0489(19) Uani 0.5 1 d D U P D 2
N2' N 0.930(2) 0.7512(7) 0.4617(9) 0.071(2) Uani 0.5 1 d D U P D 2
C10' C 1.006(3) 0.6087(13) 0.3453(11) 0.047(2) Uani 0.5 1 d D U P D 2
N3' N 1.115(3) 0.5954(12) 0.3044(11) 0.066(3) Uani 0.5 1 d D U P D 2
C11 C 0.5647(2) 0.53511(10) 0.29218(10) 0.0397(3) Uani 1 1 d . U . . .
H11A H 0.445133 0.553031 0.308550 0.048 Uiso 1 1 calc R U . E 1
C12 C 0.53494(17) 0.46650(6) 0.24796(7) 0.0419(4) Uani 1 1 d G U . . .
C13 C 0.36077(14) 0.44500(9) 0.23277(9) 0.0580(5) Uani 1 1 d G U . . .
H13A H 0.263027 0.472281 0.251388 0.070 Uiso 1 1 calc R U . . .
C14 C 0.32960(17) 0.38360(10) 0.19035(10) 0.0739(8) Uani 1 1 d DG U . . .
C15 C 0.4726(2) 0.34369(8) 0.16312(9) 0.0704(7) Uani 1 1 d DG U . . .
C16 C 0.6468(2) 0.36518(8) 0.17830(9) 0.0603(6) Uani 1 1 d DG U . . .
C17 C 0.67795(14) 0.42659(8) 0.22072(8) 0.0501(4) Uani 1 1 d G U . . .
H17A H 0.796989 0.441274 0.231103 0.060 Uiso 1 1 calc R U . . .
C18 C 0.6455(3) 0.59331(11) 0.24422(11) 0.0481(4) Uani 1 1 d . U . F 1
H18A H 0.749861 0.580981 0.217619 0.058 Uiso 1 1 calc R U . F 1
C19 C 0.5821(4) 0.65924(13) 0.23674(15) 0.0609(6) Uani 1 1 d . U . F 1
H19A H 0.482649 0.672662 0.265831 0.073 Uiso 1 1 calc R U . F 1
C20 C 0.6549(5) 0.71539(17) 0.1855(2) 0.0856(10) Uani 1 1 d . U . F 1
H20A H 0.556535 0.737076 0.157839 0.128 Uiso 1 1 calc R U . F 1
H20B H 0.739417 0.692128 0.152131 0.128 Uiso 1 1 calc R U . F 1
H20C H 0.716449 0.753643 0.212979 0.128 Uiso 1 1 calc R U . F 1
C21 C 0.27154(17) 0.38933(5) 0.51443(5) 0.0384(3) Uani 1 1 d G U . . .
C22 C 0.2673(2) 0.39838(5) 0.58914(6) 0.0487(4) Uani 1 1 d G U . G .
H22A H 0.239972 0.444802 0.609267 0.058 Uiso 1 1 calc R U . . .
C23 C 0.3030(2) 0.33949(7) 0.63438(5) 0.0543(5) Uani 1 1 d G U . G .
H23A H 0.300117 0.345676 0.685436 0.065 Uiso 1 1 calc R U . . .
C24 C 0.3430(2) 0.27157(6) 0.60493(7) 0.0481(4) Uani 1 1 d G U . G .
C25 C 0.3472(2) 0.26253(5) 0.53023(7) 0.0510(5) Uani 1 1 d G U . G .
H25A H 0.374571 0.216101 0.510095 0.061 Uiso 1 1 calc R U . . .
C26 C 0.3115(2) 0.32141(6) 0.48498(5) 0.0483(4) Uani 1 1 d G U . G .
H26A H 0.314427 0.315226 0.433924 0.058 Uiso 1 1 calc R U . . .
C27 C 0.3764(4) 0.20628(15) 0.65415(18) 0.0717(7) Uani 1 1 d . U . . .
H27A H 0.472429 0.176174 0.633829 0.108 Uiso 1 1 calc R U . G .
H27B H 0.267034 0.177110 0.657959 0.108 Uiso 1 1 calc R U . . .
H27C H 0.411413 0.223516 0.702342 0.108 Uiso 1 1 calc R U . . .
S3 S 0.2370(5) 0.4599(2) 0.4552(2) 0.0583(11) Uani 0.5 1 d D U P G 1
O1 O 0.1212(11) 0.5119(6) 0.4869(8) 0.069(3) Uani 0.5 1 d D U P G 1
O2 O 0.194(2) 0.4263(8) 0.3876(7) 0.076(3) Uani 0.5 1 d D U P G 1
S3' S 0.2325(5) 0.4672(2) 0.45722(18) 0.0370(6) Uani 0.5 1 d D U P G 2
O1' O 0.1247(15) 0.5180(5) 0.4998(8) 0.058(2) Uani 0.5 1 d D U P G 2
O2' O 0.1704(17) 0.4400(7) 0.3890(5) 0.0472(13) Uani 0.5 1 d D U P G 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
F1 C16 1.325(11) . ?
F2 C15 1.337(9) . ?
F3 C14 1.344(10) . ?
F1' C16 1.322(14) . ?
F2' C15 1.350(10) . ?
F3' C14 1.314(11) . ?
N1 C5 1.480(2) . ?
N1 C1 1.481(2) . ?
N1 S3' 1.621(4) . ?
N1 S3 1.649(4) . ?
C1 C2 1.527(3) . ?
C1 C7 1.543(3) . ?
C1 H1A 1.0000 . ?
C2 C3 1.500(3) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 C8 1.348(3) . ?
C3 C4 1.515(2) . ?
C4 C5 1.547(2) . ?
C4 C11 1.569(2) . ?
C4 H4A 1.0000 . ?
C5 C6 1.540(2) . ?
C5 H5A 1.0000 . ?
C6 C7 1.539(3) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 C9 1.321(15) . ?
C8 C10' 1.333(17) . ?
C8 C9' 1.537(11) . ?
C8 C10 1.545(14) . ?
C9 N2 1.131(12) . ?
C10 N3 1.137(12) . ?
C9' N2' 1.137(11) . ?
C10' N3' 1.140(13) . ?
C11 C18 1.512(3) . ?
C11 C12 1.515(2) . ?
C11 H11A 1.0000 . ?
C12 C13 1.3900 . ?
C12 C17 1.3900 . ?
C13 C14 1.3900 . ?
C13 H13A 0.9500 . ?
C14 C15 1.3900 . ?
C15 C16 1.3900 . ?
C16 C17 1.3900 . ?
C17 H17A 0.9500 . ?
C18 C19 1.304(3) . ?
C18 H18A 0.9500 . ?
C19 C20 1.500(3) . ?
C19 H19A 0.9500 . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
C21 C22 1.3900 . ?
C21 C26 1.3900 . ?
C21 S3 1.712(5) . ?
C21 S3' 1.799(4) . ?
C22 C23 1.3900 . ?
C22 H22A 0.9500 . ?
C23 C24 1.3900 . ?
C23 H23A 0.9500 . ?
C24 C25 1.3900 . ?
C24 C27 1.523(2) . ?
C25 C26 1.3900 . ?
C25 H25A 0.9500 . ?
C26 H26A 0.9500 . ?
C27 H27A 0.9800 . ?
C27 H27B 0.9800 . ?
C27 H27C 0.9800 . ?
S3 O1 1.415(9) . ?
S3 O2 1.429(11) . ?
S3' O2' 1.432(10) . ?
S3' O1' 1.461(9) . ?

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
C5 N1 C1 103.71(13) . . ?
C5 N1 S3' 123.15(17) . . ?
C1 N1 S3' 119.53(16) . . ?
C5 N1 S3 118.22(19) . . ?
C1 N1 S3 122.70(19) . . ?
N1 C1 C2 104.66(15) . . ?
N1 C1 C7 104.64(15) . . ?
C2 C1 C7 111.69(16) . . ?
N1 C1 H1A 111.8 . . ?
C2 C1 H1A 111.8 . . ?
C7 C1 H1A 111.8 . . ?
C3 C2 C1 111.01(15) . . ?
C3 C2 H2A 109.4 . . ?
C1 C2 H2A 109.4 . . ?
C3 C2 H2B 109.4 . . ?
C1 C2 H2B 109.4 . . ?
H2A C2 H2B 108.0 . . ?
C8 C3 C2 119.99(17) . . ?
C8 C3 C4 121.82(18) . . ?
C2 C3 C4 118.18(15) . . ?
C3 C4 C5 109.13(14) . . ?
C3 C4 C11 111.21(13) . . ?
C5 C4 C11 110.81(14) . . ?
C3 C4 H4A 108.5 . . ?
C5 C4 H4A 108.5 . . ?
C11 C4 H4A 108.5 . . ?
N1 C5 C6 104.14(14) . . ?
N1 C5 C4 107.09(13) . . ?
C6 C5 C4 112.04(13) . . ?
N1 C5 H5A 111.1 . . ?
C6 C5 H5A 111.1 . . ?
C4 C5 H5A 111.1 . . ?
C7 C6 C5 104.69(14) . . ?
C7 C6 H6A 110.8 . . ?
C5 C6 H6A 110.8 . . ?
C7 C6 H6B 110.8 . . ?
C5 C6 H6B 110.8 . . ?
H6A C6 H6B 108.9 . . ?
C6 C7 C1 104.93(15) . . ?
C6 C7 H7A 110.8 . . ?
C1 C7 H7A 110.8 . . ?
C6 C7 H7B 110.8 . . ?
C1 C7 H7B 110.8 . . ?
H7A C7 H7B 108.8 . . ?
C9 C8 C3 125.0(11) . . ?
C10' C8 C3 127.2(9) . . ?
C10' C8 C9' 113.0(12) . . ?
C3 C8 C9' 119.6(8) . . ?
C9 C8 C10 117.2(13) . . ?
C3 C8 C10 117.8(8) . . ?
N2 C9 C8 171(2) . . ?
N3 C10 C8 177(2) . . ?
N2' C9' C8 176.0(17) . . ?
N3' C10' C8 178(3) . . ?
C18 C11 C12 109.11(15) . . ?
C18 C11 C4 113.15(15) . . ?
C12 C11 C4 111.36(13) . . ?
C18 C11 H11A 107.7 . . ?
C12 C11 H11A 107.7 . . ?
C4 C11 H11A 107.7 . . ?
C13 C12 C17 120.0 . . ?
C13 C12 C11 118.79(10) . . ?
C17 C12 C11 121.18(10) . . ?
C12 C13 C14 120.0 . . ?
C12 C13 H13A 120.0 . . ?
C14 C13 H13A 120.0 . . ?
F3' C14 C15 119.3(12) . . ?
F3 C14 C15 117.7(9) . . ?
F3' C14 C13 119.8(11) . . ?
F3 C14 C13 121.5(9) . . ?
C15 C14 C13 120.0 . . ?
F2 C15 C16 117.2(8) . . ?
F2' C15 C16 121.5(7) . . ?
F2 C15 C14 122.7(8) . . ?
F2' C15 C14 118.3(7) . . ?
C16 C15 C14 120.0 . . ?
F1' C16 C15 117.3(17) . . ?
F1 C16 C15 119.3(14) . . ?
F1' C16 C17 122.1(17) . . ?
F1 C16 C17 120.4(14) . . ?
C15 C16 C17 120.0 . . ?
C16 C17 C12 120.0 . . ?
C16 C17 H17A 120.0 . . ?
C12 C17 H17A 120.0 . . ?
C19 C18 C11 124.7(2) . . ?
C19 C18 H18A 117.7 . . ?
C11 C18 H18A 117.7 . . ?
C18 C19 C20 124.7(3) . . ?
C18 C19 H19A 117.7 . . ?
C20 C19 H19A 117.7 . . ?
C19 C20 H20A 109.5 . . ?
C19 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C19 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C22 C21 C26 120.0 . . ?
C22 C21 S3 122.74(16) . . ?
C26 C21 S3 117.22(16) . . ?
C22 C21 S3' 119.01(12) . . ?
C26 C21 S3' 120.95(12) . . ?
C21 C22 C23 120.0 . . ?
C21 C22 H22A 120.0 . . ?
C23 C22 H22A 120.0 . . ?
C24 C23 C22 120.0 . . ?
C24 C23 H23A 120.0 . . ?
C22 C23 H23A 120.0 . . ?
C23 C24 C25 120.0 . . ?
C23 C24 C27 120.27(15) . . ?
C25 C24 C27 119.70(15) . . ?
C24 C25 C26 120.0 . . ?
C24 C25 H25A 120.0 . . ?
C26 C25 H25A 120.0 . . ?
C25 C26 C21 120.0 . . ?
C25 C26 H26A 120.0 . . ?
C21 C26 H26A 120.0 . . ?
C24 C27 H27A 109.5 . . ?
C24 C27 H27B 109.5 . . ?
H27A C27 H27B 109.5 . . ?
C24 C27 H27C 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?
O1 S3 O2 120.7(8) . . ?
O1 S3 N1 103.8(5) . . ?
O2 S3 N1 106.6(7) . . ?
O1 S3 C21 109.7(6) . . ?
O2 S3 C21 105.6(6) . . ?
N1 S3 C21 110.2(3) . . ?
O2' S3' O1' 121.1(8) . . ?
O2' S3' N1 106.8(6) . . ?
O1' S3' N1 107.8(5) . . ?
O2' S3' C21 107.1(5) . . ?
O1' S3' C21 106.1(6) . . ?
N1 S3' C21 107.4(2) . . ?

_refine_diff_density_max         0.303
_refine_diff_density_min         -0.146
_refine_diff_density_rms         0.035


loop_
_publcif_info_exptl_table_extra_item
sin_theta_over_lambda_max

loop_
_publcif_info_exptl_table_header_item
?



_publcif_funding_html            
;
;
####################################################################### 
# 
# 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_lova3
_database_code_depnum_ccdc_archive 'CCDC 2193763'
loop_
_audit_author_name
_audit_author_address
'Khalil A Abboud'
;University of Florida
United States of America
;
_audit_update_record             
;
2022-07-30 deposited with the CCDC.	2023-02-13 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         ?
_chemical_formula_sum            'C23 H24 Cl N O4 S'
_chemical_formula_weight         445.94

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 21'
_space_group_name_Hall           'P 2yb'

_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'

_cell_length_a                   11.1508(4)
_cell_length_b                   6.3344(2)
_cell_length_c                   15.0399(5)
_cell_angle_alpha                90
_cell_angle_beta                 99.4170(10)
_cell_angle_gamma                90
_cell_volume                     1048.01(6)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    8580
_cell_measurement_theta_min      2.48
_cell_measurement_theta_max      32.44

_exptl_crystal_description       plate
_exptl_crystal_colour            ?

_exptl_crystal_density_meas      .

_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.413
_exptl_crystal_F_000             468

_exptl_transmission_factor_min   0.4626
_exptl_transmission_factor_max   0.5657

_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_absorpt_coefficient_mu    0.313
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?

_exptl_absorpt_correction_type   multi-scan

_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?

_exptl_absorpt_process_details   
'Sheldrick, G. M., sadabs (2015). Acta Cryst. C71, 3-8.'

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'micro source 3.0'
_diffrn_measurement_device_type  'D8 Venture with PHOTON III'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?

_diffrn_reflns_number            22288
_diffrn_reflns_av_unetI/netI     0.0473
_diffrn_reflns_av_R_equivalents  0.0447
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         1.851
_diffrn_reflns_theta_max         32.747
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.918
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.918
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.879
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             6791
_reflns_number_gt                6055
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.778
_reflns_Friedel_fraction_max     0.834
_reflns_Friedel_fraction_full    0.999

_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       'Bruker APEX3 (Bruker, 2019)'
_computing_cell_refinement       'Bruker APEX3 (Bruker, 2019)'
_computing_data_reduction        'Bruker Apex3 SAINT (Bruker, 2019)'
_computing_structure_solution    'SHELXL2015, Sheldrick G. M. 2019'
_computing_structure_refinement  'SHELXL2015, Sheldrick G. M. 2019'
_computing_molecular_graphics    'XP in SHELXTL-plus, Bruker 2019'
_computing_publication_material  'SHELXL2015, Sheldrick, G. M. 2019'

_refine_special_details          
;
All H atoms were positioned geometrically ( C---H = 0.93/1.00 Å) and   
allowed to ride with Uiso(H)= 1.2/1.5Ueq(C).
Methyl ones were allowed to rotate around the corresponding C---C.

The stereochemistry is decided by anomalous dispersion and the value of the Flack x parameter; 0.01(2).
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0389P)²+0.1045P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_primary     direct
_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 2424 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   0.01(2)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         6791
_refine_ls_number_parameters     248
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0426
_refine_ls_R_factor_gt           0.0345
_refine_ls_wR_factor_ref         0.0849
_refine_ls_wR_factor_gt          0.0818
_refine_ls_goodness_of_fit_ref   1.074
_refine_ls_restrained_S_all      1.073
_refine_ls_shift/su_max          0.001
_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 0.27565(5) 0.42431(12) -0.06044(3) 0.03620(16) Uani 1 1 d . . . . .
S3 S 0.94500(4) 0.18958(7) 0.29942(3) 0.01557(10) Uani 1 1 d . . . . .
O1 O 1.03853(13) 0.1106(2) 0.36854(10) 0.0211(3) Uani 1 1 d . . . . .
O2 O 0.88332(13) 0.0514(2) 0.23125(9) 0.0210(3) Uani 1 1 d . . . . .
O3 O 0.47035(13) 0.1267(3) 0.46518(9) 0.0229(3) Uani 1 1 d . . . . .
O4 O 0.60581(13) 0.1637(2) 0.58709(9) 0.0216(3) Uani 1 1 d . . . . .
N1 N 0.84033(14) 0.2860(3) 0.35164(10) 0.0151(3) Uani 1 1 d . . . . .
C1 C 0.86945(17) 0.4242(3) 0.43219(12) 0.0172(3) Uani 1 1 d . . . . .
H1 H 0.957153 0.412336 0.459587 0.021 Uiso 1 1 calc R U . . .
C2 C 0.78632(17) 0.3490(3) 0.49865(12) 0.0175(4) Uani 1 1 d . . . . .
H2A H 0.833256 0.258420 0.545570 0.021 Uiso 1 1 calc R U . . .
H2AB H 0.756150 0.472522 0.528728 0.021 Uiso 1 1 calc R U . . .
C3 C 0.67824(17) 0.2242(3) 0.44784(12) 0.0157(4) Uani 1 1 d . . . . .
H3 H 0.711906 0.084815 0.432677 0.019 Uiso 1 1 calc R U . . .
C4 C 0.62429(17) 0.3253(3) 0.35756(12) 0.0147(3) Uani 1 1 d . . . . .
H4 H 0.583533 0.460066 0.370216 0.018 Uiso 1 1 calc R U . . .
C5 C 0.72683(16) 0.3785(3) 0.30236(12) 0.0163(3) Uani 1 1 d . . . . .
H5 H 0.707718 0.323716 0.239275 0.020 Uiso 1 1 calc R U . . .
C6 C 0.75364(19) 0.6167(3) 0.30435(14) 0.0222(4) Uani 1 1 d . . . . .
H6A H 0.677971 0.699737 0.301950 0.027 Uiso 1 1 calc R U . . .
H6AB H 0.794303 0.658367 0.253248 0.027 Uiso 1 1 calc R U . . .
C7 C 0.8389(2) 0.6489(3) 0.39542(14) 0.0236(4) Uani 1 1 d . . . . .
H7A H 0.913714 0.724566 0.386518 0.028 Uiso 1 1 calc R U . . .
H7AB H 0.797640 0.731029 0.437575 0.028 Uiso 1 1 calc R U . . .
C8 C 0.58391(17) 0.1752(3) 0.50585(12) 0.0170(3) Uani 1 1 d . . . . .
C9 C 0.42752(17) 0.1556(3) 0.36905(12) 0.0196(4) Uani 1 1 d . . . . .
H9A H 0.377048 0.284942 0.360772 0.024 Uiso 1 1 calc R U . . .
H9AB H 0.374449 0.034990 0.346998 0.024 Uiso 1 1 calc R U . . .
C10 C 0.52707(16) 0.1739(3) 0.31054(12) 0.0171(3) Uani 1 1 d . . . . .
H10 H 0.564916 0.031766 0.306864 0.020 Uiso 1 1 calc R U . . .
C11 C 0.46927(12) 0.24073(19) 0.21586(6) 0.0183(4) Uani 1 1 d G . . . .
C12 C 0.46590(12) 0.10051(17) 0.14440(8) 0.0224(4) Uani 1 1 d G . . . .
H12 H 0.502865 -0.034463 0.154114 0.027 Uiso 1 1 calc R U . . .
C13 C 0.40844(13) 0.1578(2) 0.05873(7) 0.0268(5) Uani 1 1 d G . . . .
H13 H 0.406140 0.061936 0.009891 0.032 Uiso 1 1 calc R U . . .
C14 C 0.35436(12) 0.3553(2) 0.04451(6) 0.0258(5) Uani 1 1 d G . . . .
C15 C 0.35773(13) 0.49548(18) 0.11597(8) 0.0268(5) Uani 1 1 d G . . . .
H15 H 0.320767 0.630449 0.106253 0.032 Uiso 1 1 calc R U . . .
C16 C 0.41519(13) 0.43822(18) 0.20164(7) 0.0233(4) Uani 1 1 d G . . . .
H16 H 0.417491 0.534054 0.250477 0.028 Uiso 1 1 calc R U . . .
C17 C 1.00842(11) 0.39596(17) 0.24410(7) 0.0165(3) Uani 1 1 d G . . . .
C18 C 1.10287(11) 0.5147(2) 0.29116(6) 0.0190(4) Uani 1 1 d G . . . .
H18 H 1.138534 0.474769 0.350498 0.023 Uiso 1 1 calc R U . . .
C19 C 1.14512(10) 0.6919(2) 0.25140(8) 0.0206(4) Uani 1 1 d G . . . .
H19 H 1.209670 0.773122 0.283564 0.025 Uiso 1 1 calc R U . . .
C20 C 1.09293(12) 0.75041(18) 0.16458(8) 0.0200(4) Uani 1 1 d G . . . .
C21 C 0.99849(11) 0.6316(2) 0.11752(6) 0.0217(4) Uani 1 1 d G . . . .
H21 H 0.962819 0.671599 0.058187 0.026 Uiso 1 1 calc R U . . .
C22 C 0.95623(10) 0.45442(19) 0.15728(7) 0.0206(4) Uani 1 1 d G . . . .
H22 H 0.891682 0.373245 0.125120 0.025 Uiso 1 1 calc R U . . .
C23 C 1.1329(2) 0.9501(4) 0.12261(15) 0.0283(5) Uani 1 1 d . . . . .
H23A H 1.160567 0.915570 0.065779 0.042 Uiso 1 1 calc R U . . .
H23B H 1.199556 1.015562 0.163972 0.042 Uiso 1 1 calc R U . . .
H23C H 1.064325 1.048645 0.110899 0.042 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 C14 1.7321 . ?
S3 O2 1.4352(14) . ?
S3 O1 1.4366(14) . ?
S3 N1 1.6284(17) . ?
S3 C17 1.7590(10) . ?
O3 C8 1.349(2) . ?
O3 C9 1.458(2) . ?
O4 C8 1.208(2) . ?
N1 C5 1.479(2) . ?
N1 C1 1.487(2) . ?
C1 C7 1.545(3) . ?
C1 C2 1.545(3) . ?
C1 H1 1.0000 . ?
C2 C3 1.536(2) . ?
C2 H2A 0.9900 . ?
C2 H2AB 0.9900 . ?
C3 C8 1.505(3) . ?
C3 C4 1.533(2) . ?
C3 H3 1.0000 . ?
C4 C10 1.531(3) . ?
C4 C5 1.556(3) . ?
C4 H4 1.0000 . ?
C5 C6 1.537(3) . ?
C5 H5 1.0000 . ?
C6 C7 1.548(3) . ?
C6 H6A 0.9900 . ?
C6 H6AB 0.9900 . ?
C7 H7A 0.9900 . ?
C7 H7AB 0.9900 . ?
C9 C10 1.530(3) . ?
C9 H9A 0.9900 . ?
C9 H9AB 0.9900 . ?
C10 C11 1.5238(19) . ?
C10 H10 1.0000 . ?
C11 C12 1.3900 . ?
C11 C16 1.3900 . ?
C12 C13 1.3900 . ?
C12 H12 0.9500 . ?
C13 C14 1.3900 . ?
C13 H13 0.9500 . ?
C14 C15 1.3900 . ?
C15 C16 1.3900 . ?
C15 H15 0.9500 . ?
C16 H16 0.9500 . ?
C17 C18 1.3900 . ?
C17 C22 1.3900 . ?
C18 C19 1.3900 . ?
C18 H18 0.9500 . ?
C19 C20 1.3900 . ?
C19 H19 0.9500 . ?
C20 C21 1.3900 . ?
C20 C23 1.513(2) . ?
C21 C22 1.3900 . ?
C21 H21 0.9500 . ?
C22 H22 0.9500 . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 0.9800 . ?

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 S3 O1 120.73(9) . . ?
O2 S3 N1 106.01(8) . . ?
O1 S3 N1 105.92(8) . . ?
O2 S3 C17 107.35(8) . . ?
O1 S3 C17 107.49(8) . . ?
N1 S3 C17 108.95(8) . . ?
C8 O3 C9 123.51(15) . . ?
C5 N1 C1 103.28(14) . . ?
C5 N1 S3 121.94(12) . . ?
C1 N1 S3 122.38(12) . . ?
N1 C1 C7 104.17(15) . . ?
N1 C1 C2 105.75(15) . . ?
C7 C1 C2 113.28(17) . . ?
N1 C1 H1 111.1 . . ?
C7 C1 H1 111.1 . . ?
C2 C1 H1 111.1 . . ?
C3 C2 C1 109.98(14) . . ?
C3 C2 H2A 109.7 . . ?
C1 C2 H2A 109.7 . . ?
C3 C2 H2AB 109.7 . . ?
C1 C2 H2AB 109.7 . . ?
H2A C2 H2AB 108.2 . . ?
C8 C3 C4 112.93(15) . . ?
C8 C3 C2 112.56(15) . . ?
C4 C3 C2 112.82(15) . . ?
C8 C3 H3 105.9 . . ?
C4 C3 H3 105.9 . . ?
C2 C3 H3 105.9 . . ?
C10 C4 C3 107.05(15) . . ?
C10 C4 C5 114.58(15) . . ?
C3 C4 C5 110.31(14) . . ?
C10 C4 H4 108.2 . . ?
C3 C4 H4 108.2 . . ?
C5 C4 H4 108.2 . . ?
N1 C5 C6 103.38(15) . . ?
N1 C5 C4 106.85(14) . . ?
C6 C5 C4 111.09(16) . . ?
N1 C5 H5 111.7 . . ?
C6 C5 H5 111.7 . . ?
C4 C5 H5 111.7 . . ?
C5 C6 C7 103.65(15) . . ?
C5 C6 H6A 111.0 . . ?
C7 C6 H6A 111.0 . . ?
C5 C6 H6AB 111.0 . . ?
C7 C6 H6AB 111.0 . . ?
H6A C6 H6AB 109.0 . . ?
C1 C7 C6 105.25(15) . . ?
C1 C7 H7A 110.7 . . ?
C6 C7 H7A 110.7 . . ?
C1 C7 H7AB 110.7 . . ?
C6 C7 H7AB 110.7 . . ?
H7A C7 H7AB 108.8 . . ?
O4 C8 O3 117.67(17) . . ?
O4 C8 C3 123.64(17) . . ?
O3 C8 C3 118.52(15) . . ?
O3 C9 C10 115.42(15) . . ?
O3 C9 H9A 108.4 . . ?
C10 C9 H9A 108.4 . . ?
O3 C9 H9AB 108.4 . . ?
C10 C9 H9AB 108.4 . . ?
H9A C9 H9AB 107.5 . . ?
C11 C10 C9 108.84(14) . . ?
C11 C10 C4 114.65(15) . . ?
C9 C10 C4 107.90(15) . . ?
C11 C10 H10 108.4 . . ?
C9 C10 H10 108.4 . . ?
C4 C10 H10 108.4 . . ?
C12 C11 C16 120.0 . . ?
C12 C11 C10 119.93(11) . . ?
C16 C11 C10 120.01(11) . . ?
C11 C12 C13 120.0 . . ?
C11 C12 H12 120.0 . . ?
C13 C12 H12 120.0 . . ?
C14 C13 C12 120.0 . . ?
C14 C13 H13 120.0 . . ?
C12 C13 H13 120.0 . . ?
C15 C14 C13 120.0 . . ?
C15 C14 Cl1 119.26(8) . . ?
C13 C14 Cl1 120.65(8) . . ?
C14 C15 C16 120.0 . . ?
C14 C15 H15 120.0 . . ?
C16 C15 H15 120.0 . . ?
C15 C16 C11 120.0 . . ?
C15 C16 H16 120.0 . . ?
C11 C16 H16 120.0 . . ?
C18 C17 C22 120.0 . . ?
C18 C17 S3 119.42(7) . . ?
C22 C17 S3 120.23(7) . . ?
C19 C18 C17 120.0 . . ?
C19 C18 H18 120.0 . . ?
C17 C18 H18 120.0 . . ?
C18 C19 C20 120.0 . . ?
C18 C19 H19 120.0 . . ?
C20 C19 H19 120.0 . . ?
C21 C20 C19 120.0 . . ?
C21 C20 C23 119.36(12) . . ?
C19 C20 C23 120.54(12) . . ?
C20 C21 C22 120.0 . . ?
C20 C21 H21 120.0 . . ?
C22 C21 H21 120.0 . . ?
C21 C22 C17 120.0 . . ?
C21 C22 H22 120.0 . . ?
C17 C22 H22 120.0 . . ?
C20 C23 H23A 109.5 . . ?
C20 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
C20 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?

_refine_diff_density_max         0.386
_refine_diff_density_min         -0.313
_refine_diff_density_rms         0.054

