# Electronic Supplementary Material (ESI) for CrystEngComm.
# 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_1_AUTO
_database_code_depnum_ccdc_archive 'CCDC 2241333'
loop_
_audit_author_name
_audit_author_address
'Muhammad Nawaz Tahir'
;University of Sargodha, Pakistan
Pakistan
;
_audit_update_record             
;
2023-10-06 deposited with the CCDC.	2023-10-23 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2019/2
_shelx_SHELXL_version_number     2019/2
_chemical_name_common            ?
_chemical_absolute_configuration .
_chemical_name_systematic        
;
2-[(4-Tertbutylphenylmethyl)sulfanyl]-5-(phenyl)-1,3,4-oxadiazole
;
_chemical_formula_moiety         'C19 H20 N2 O S'
_chemical_formula_sum            'C19 H20 N2 O S'
_chemical_formula_iupac          'C19 H20 N2 O S'
_chemical_formula_weight         324.43

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'

_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                   10.50070(10)
_cell_length_b                   19.5547(2)
_cell_length_c                   8.63490(10)
_cell_angle_alpha                90
_cell_angle_beta                 97.9410(10)
_cell_angle_gamma                90
_cell_volume                     1756.07(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3204
_cell_measurement_theta_min      4.522
_cell_measurement_theta_max      76.398
_cell_measurement_temperature    296(2)
_exptl_crystal_description       rod
_exptl_crystal_colour            'light yellow'
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.22
_exptl_crystal_density_diffrn    1.227
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             688
_exptl_absorpt_coefficient_mu    1.672
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.73a (Rigaku Oxford Diffraction, 2022)
Empirical absorption correctionusing spherical harmonics,
implimented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_correction_T_min  0.535
_exptl_absorpt_correction_T_max  0.615
_shelx_estimated_absorpt_T_min   0.584
_shelx_estimated_absorpt_T_max   0.710
_exptl_special_details           
;
;


_diffrn_ambient_temperature      296(2)
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC11 (RINC): quarter-chi single'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 7.93
_diffrn_reflns_number            21438
_diffrn_reflns_av_unetI/netI     0.0134
_diffrn_reflns_av_R_equivalents  0.0231
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         4.522
_diffrn_reflns_theta_max         76.398
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.975
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.975
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.975
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_standards_number         0
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?

_refine_special_details          
;
Refinement of F² against ALL reflections. The weighted R-factor
wR and goodness of fit S are based on F², conventional
R-factors R are based on F, with F set to zero for
negative F². The threshold expression of F² >
σ(F²) is used only for calculating R-factors(gt) etc.
and is not relevant to the choice of reflections for refinement.
R-factors based on F² are statistically about twice as large
as those based on F, and R- factors based on ALL data will be
even larger.
;
_reflns_number_total             3589
_reflns_number_gt                3204
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0435
_refine_ls_R_factor_gt           0.0405
_refine_ls_wR_factor_ref         0.1225
_refine_ls_wR_factor_gt          0.1194
_refine_ls_goodness_of_fit_ref   1.090
_refine_ls_restrained_S_all      1.099
_refine_ls_number_reflns         3589
_refine_ls_number_parameters     219
_refine_ls_number_restraints     12
_refine_ls_hydrogen_treatment    constr
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0717P)²+0.1517P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_refine_ls_extinction_method     'SHELXL-2019/2 (Sheldrick 2019)'
_refine_ls_extinction_coef       0.0062(8)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_computing_data_collection       'APEX2 (Bruker, 2007)'
_computing_cell_refinement       'SAINT (Bruker, 2007)'
_computing_data_reduction        'SAINT (Bruker, 2007)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2019/2  (Sheldrick, 2019)'
_computing_molecular_graphics    
'ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 2009)'
_computing_publication_material  
;
WinGX (Farrugia, 1999) and PLATON (Spek, 2009)
;

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 0.37626(4) 0.08594(2) 0.90287(4) 0.07390(18) Uani 1 1 d . . . . .
O1 O 0.50391(10) 0.08308(4) 1.19150(11) 0.0614(3) Uani 1 1 d . . . . .
N1 N 0.46216(13) 0.18777(6) 1.10569(14) 0.0705(3) Uani 1 1 d . . . . .
N2 N 0.52667(13) 0.19116(6) 1.25987(14) 0.0688(3) Uani 1 1 d . . . . .
C1 C 0.45108(13) 0.12410(7) 1.07252(15) 0.0579(3) Uani 1 1 d . . . . .
C2 C 0.54853(12) 0.12963(6) 1.30511(14) 0.0537(3) Uani 1 1 d . . . . .
C3 C 0.31872(17) 0.16459(8) 0.80480(17) 0.0725(4) Uani 1 1 d . . . . .
H3A H 0.270313 0.190481 0.872702 0.087 Uiso 1 1 calc R U . . .
H3B H 0.391843 0.192078 0.785663 0.087 Uiso 1 1 calc R U . . .
C4 C 0.23481(14) 0.15125(7) 0.65202(16) 0.0624(3) Uani 1 1 d . . . . .
C5 C 0.27365(13) 0.17191(7) 0.51348(16) 0.0607(3) Uani 1 1 d . . . . .
H5 H 0.355624 0.189978 0.513883 0.073 Uiso 1 1 calc R U . . .
C6 C 0.19223(13) 0.16615(7) 0.37343(15) 0.0584(3) Uani 1 1 d . . . . .
H6 H 0.220898 0.180673 0.281678 0.070 Uiso 1 1 calc R U . . .
C7 C 0.06956(13) 0.13944(7) 0.36611(15) 0.0587(3) Uani 1 1 d . . . . .
C8 C 0.03290(15) 0.11758(10) 0.50658(18) 0.0802(5) Uani 1 1 d . . . . .
H8 H -0.048367 0.098653 0.506399 0.096 Uiso 1 1 calc R U . . .
C9 C 0.11328(17) 0.12314(10) 0.64569(18) 0.0822(5) Uani 1 1 d . . . . .
H9 H 0.085507 0.107729 0.737274 0.099 Uiso 1 1 calc R U . . .
C10 C -0.02315(14) 0.13531(9) 0.21409(17) 0.0734(4) Uani 1 1 d D . . . .
C11A C 0.0407(2) 0.14867(19) 0.0716(2) 0.1137(10) Uani 0.869(3) 1 d D . P A 1
H11A H -0.021908 0.145429 -0.020326 0.171 Uiso 0.869(3) 1 calc R U P A 1
H11B H 0.077561 0.193675 0.078060 0.171 Uiso 0.869(3) 1 calc R U P A 1
H11C H 0.107180 0.115432 0.065963 0.171 Uiso 0.869(3) 1 calc R U P A 1
C12A C -0.0903(3) 0.06572(17) 0.2034(3) 0.1319(13) Uani 0.869(3) 1 d D . P A 1
H12A H -0.130208 0.058373 0.295479 0.198 Uiso 0.869(3) 1 calc R U P A 1
H12B H -0.154538 0.064737 0.112802 0.198 Uiso 0.869(3) 1 calc R U P A 1
H12C H -0.028140 0.030357 0.195055 0.198 Uiso 0.869(3) 1 calc R U P A 1
C13A C -0.1276(2) 0.19013(18) 0.2219(3) 0.1262(11) Uani 0.869(3) 1 d D . P A 1
H13A H -0.169364 0.182338 0.312435 0.189 Uiso 0.869(3) 1 calc R U P A 1
H13B H -0.088600 0.234635 0.228677 0.189 Uiso 0.869(3) 1 calc R U P A 1
H13C H -0.189749 0.187554 0.129515 0.189 Uiso 0.869(3) 1 calc R U P A 1
C11B C 0.0320(14) 0.0800(7) 0.1115(15) 0.1137(10) Uani 0.131(3) 1 d D . P A 2
H11D H 0.120597 0.089967 0.104852 0.171 Uiso 0.131(3) 1 calc R U P A 2
H11E H 0.025431 0.035819 0.158050 0.171 Uiso 0.131(3) 1 calc R U P A 2
H11F H -0.016102 0.080310 0.008571 0.171 Uiso 0.131(3) 1 calc R U P A 2
C12B C -0.1608(10) 0.1182(11) 0.222(2) 0.1319(13) Uani 0.131(3) 1 d D . P A 2
H12D H -0.207350 0.117453 0.118022 0.198 Uiso 0.131(3) 1 calc R U P A 2
H12E H -0.166035 0.074152 0.269424 0.198 Uiso 0.131(3) 1 calc R U P A 2
H12F H -0.197344 0.152133 0.282943 0.198 Uiso 0.131(3) 1 calc R U P A 2
C13B C -0.0212(15) 0.2036(6) 0.124(2) 0.1262(11) Uani 0.131(3) 1 d D . P A 2
H13D H 0.066188 0.216163 0.116916 0.189 Uiso 0.131(3) 1 calc R U P A 2
H13E H -0.067472 0.198295 0.020919 0.189 Uiso 0.131(3) 1 calc R U P A 2
H13F H -0.060972 0.238653 0.178685 0.189 Uiso 0.131(3) 1 calc R U P A 2
C14 C 0.61139(12) 0.10558(7) 1.45600(15) 0.0557(3) Uani 1 1 d . . . . .
C15 C 0.63772(15) 0.15220(8) 1.57733(18) 0.0705(4) Uani 1 1 d . . . . .
H15 H 0.615800 0.197984 1.561386 0.085 Uiso 1 1 calc R U . . .
C16 C 0.69612(19) 0.13057(10) 1.7208(2) 0.0874(5) Uani 1 1 d . . . . .
H16 H 0.713410 0.161642 1.802509 0.105 Uiso 1 1 calc R U . . .
C17 C 0.72935(19) 0.06248(11) 1.7439(2) 0.0922(5) Uani 1 1 d . . . . .
H17 H 0.769078 0.047978 1.841261 0.111 Uiso 1 1 calc R U . . .
C18 C 0.70429(17) 0.01654(9) 1.6249(2) 0.0840(5) Uani 1 1 d . . . . .
H18 H 0.727490 -0.029059 1.641357 0.101 Uiso 1 1 calc R U . . .
C19 C 0.64463(14) 0.03738(7) 1.48021(17) 0.0668(4) Uani 1 1 d . . . . .
H19 H 0.626815 0.005899 1.399403 0.080 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
S1 C1 1.7327(13) . ?
S1 C3 1.8183(15) . ?
O1 C1 1.3598(15) . ?
O1 C2 1.3724(15) . ?
N1 C1 1.2793(17) . ?
N1 N2 1.4094(17) . ?
N2 C2 1.2761(16) . ?
C2 C14 1.4549(17) . ?
C3 C4 1.5046(18) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C4 C5 1.3768(19) . ?
C4 C9 1.384(2) . ?
C5 C6 1.3857(18) . ?
C5 H5 0.9300 . ?
C6 C7 1.3833(19) . ?
C6 H6 0.9300 . ?
C7 C8 1.390(2) . ?
C7 C10 1.5246(19) . ?
C8 C9 1.374(2) . ?
C8 H8 0.9300 . ?
C9 H9 0.9300 . ?
C10 C12B 1.493(9) . ?
C10 C11A 1.503(2) . ?
C10 C12A 1.529(3) . ?
C10 C13A 1.541(3) . ?
C10 C13B 1.546(9) . ?
C10 C11B 1.558(8) . ?
C11A H11A 0.9600 . ?
C11A H11B 0.9600 . ?
C11A H11C 0.9600 . ?
C12A H12A 0.9600 . ?
C12A H12B 0.9600 . ?
C12A H12C 0.9600 . ?
C13A H13A 0.9600 . ?
C13A H13B 0.9600 . ?
C13A H13C 0.9600 . ?
C11B H11D 0.9600 . ?
C11B H11E 0.9600 . ?
C11B H11F 0.9600 . ?
C12B H12D 0.9600 . ?
C12B H12E 0.9600 . ?
C12B H12F 0.9600 . ?
C13B H13D 0.9600 . ?
C13B H13E 0.9600 . ?
C13B H13F 0.9600 . ?
C14 C19 1.3870(19) . ?
C14 C15 1.3874(19) . ?
C15 C16 1.371(2) . ?
C15 H15 0.9300 . ?
C16 C17 1.384(3) . ?
C16 H16 0.9300 . ?
C17 C18 1.362(3) . ?
C17 H17 0.9300 . ?
C18 C19 1.380(2) . ?
C18 H18 0.9300 . ?
C19 H19 0.9300 . ?

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 S1 C3 96.44(6) . . ?
C1 O1 C2 102.25(10) . . ?
C1 N1 N2 105.92(11) . . ?
C2 N2 N1 106.70(11) . . ?
N1 C1 O1 112.95(11) . . ?
N1 C1 S1 128.69(10) . . ?
O1 C1 S1 118.34(9) . . ?
N2 C2 O1 112.17(11) . . ?
N2 C2 C14 128.25(12) . . ?
O1 C2 C14 119.58(11) . . ?
C4 C3 S1 112.24(10) . . ?
C4 C3 H3A 109.2 . . ?
S1 C3 H3A 109.2 . . ?
C4 C3 H3B 109.2 . . ?
S1 C3 H3B 109.2 . . ?
H3A C3 H3B 107.9 . . ?
C5 C4 C9 117.69(13) . . ?
C5 C4 C3 120.21(13) . . ?
C9 C4 C3 121.92(14) . . ?
C4 C5 C6 120.88(12) . . ?
C4 C5 H5 119.6 . . ?
C6 C5 H5 119.6 . . ?
C7 C6 C5 121.93(12) . . ?
C7 C6 H6 119.0 . . ?
C5 C6 H6 119.0 . . ?
C6 C7 C8 116.41(12) . . ?
C6 C7 C10 122.62(12) . . ?
C8 C7 C10 120.95(12) . . ?
C9 C8 C7 121.88(14) . . ?
C9 C8 H8 119.1 . . ?
C7 C8 H8 119.1 . . ?
C8 C9 C4 121.19(14) . . ?
C8 C9 H9 119.4 . . ?
C4 C9 H9 119.4 . . ?
C12B C10 C7 118.7(7) . . ?
C11A C10 C7 113.06(13) . . ?
C11A C10 C12A 111.0(2) . . ?
C7 C10 C12A 109.47(16) . . ?
C11A C10 C13A 108.4(2) . . ?
C7 C10 C13A 107.39(15) . . ?
C12A C10 C13A 107.3(2) . . ?
C12B C10 C13B 107.2(9) . . ?
C7 C10 C13B 109.6(6) . . ?
C12B C10 C11B 107.9(8) . . ?
C7 C10 C11B 106.4(5) . . ?
C13B C10 C11B 106.3(8) . . ?
C10 C11A H11A 109.5 . . ?
C10 C11A H11B 109.5 . . ?
H11A C11A H11B 109.5 . . ?
C10 C11A H11C 109.5 . . ?
H11A C11A H11C 109.5 . . ?
H11B C11A H11C 109.5 . . ?
C10 C12A H12A 109.5 . . ?
C10 C12A H12B 109.5 . . ?
H12A C12A H12B 109.5 . . ?
C10 C12A H12C 109.5 . . ?
H12A C12A H12C 109.5 . . ?
H12B C12A H12C 109.5 . . ?
C10 C13A H13A 109.5 . . ?
C10 C13A H13B 109.5 . . ?
H13A C13A H13B 109.5 . . ?
C10 C13A H13C 109.5 . . ?
H13A C13A H13C 109.5 . . ?
H13B C13A H13C 109.5 . . ?
C10 C11B H11D 109.5 . . ?
C10 C11B H11E 109.5 . . ?
H11D C11B H11E 109.5 . . ?
C10 C11B H11F 109.5 . . ?
H11D C11B H11F 109.5 . . ?
H11E C11B H11F 109.5 . . ?
C10 C12B H12D 109.5 . . ?
C10 C12B H12E 109.5 . . ?
H12D C12B H12E 109.5 . . ?
C10 C12B H12F 109.5 . . ?
H12D C12B H12F 109.5 . . ?
H12E C12B H12F 109.5 . . ?
C10 C13B H13D 109.5 . . ?
C10 C13B H13E 109.5 . . ?
H13D C13B H13E 109.5 . . ?
C10 C13B H13F 109.5 . . ?
H13D C13B H13F 109.5 . . ?
H13E C13B H13F 109.5 . . ?
C19 C14 C15 119.88(13) . . ?
C19 C14 C2 121.29(12) . . ?
C15 C14 C2 118.83(12) . . ?
C16 C15 C14 119.82(15) . . ?
C16 C15 H15 120.1 . . ?
C14 C15 H15 120.1 . . ?
C15 C16 C17 119.96(16) . . ?
C15 C16 H16 120.0 . . ?
C17 C16 H16 120.0 . . ?
C18 C17 C16 120.48(15) . . ?
C18 C17 H17 119.8 . . ?
C16 C17 H17 119.8 . . ?
C17 C18 C19 120.27(16) . . ?
C17 C18 H18 119.9 . . ?
C19 C18 H18 119.9 . . ?
C18 C19 C14 119.60(14) . . ?
C18 C19 H19 120.2 . . ?
C14 C19 H19 120.2 . . ?

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
C1 N1 N2 C2 0.07(17) . . . . ?
N2 N1 C1 O1 -0.50(17) . . . . ?
N2 N1 C1 S1 177.76(11) . . . . ?
C2 O1 C1 N1 0.70(15) . . . . ?
C2 O1 C1 S1 -177.76(9) . . . . ?
C3 S1 C1 N1 -2.43(16) . . . . ?
C3 S1 C1 O1 175.75(11) . . . . ?
N1 N2 C2 O1 0.38(16) . . . . ?
N1 N2 C2 C14 -179.24(12) . . . . ?
C1 O1 C2 N2 -0.64(15) . . . . ?
C1 O1 C2 C14 179.01(11) . . . . ?
C1 S1 C3 C4 -174.65(12) . . . . ?
S1 C3 C4 C5 -115.41(14) . . . . ?
S1 C3 C4 C9 69.71(19) . . . . ?
C9 C4 C5 C6 1.5(2) . . . . ?
C3 C4 C5 C6 -173.56(13) . . . . ?
C4 C5 C6 C7 -0.2(2) . . . . ?
C5 C6 C7 C8 -1.0(2) . . . . ?
C5 C6 C7 C10 177.52(14) . . . . ?
C6 C7 C8 C9 1.0(3) . . . . ?
C10 C7 C8 C9 -177.60(17) . . . . ?
C7 C8 C9 C4 0.3(3) . . . . ?
C5 C4 C9 C8 -1.6(3) . . . . ?
C3 C4 C9 C8 173.42(17) . . . . ?
C6 C7 C10 C12B -168.5(10) . . . . ?
C8 C7 C10 C12B 9.9(10) . . . . ?
C6 C7 C10 C11A 12.3(3) . . . . ?
C8 C7 C10 C11A -169.2(2) . . . . ?
C6 C7 C10 C12A 136.7(2) . . . . ?
C8 C7 C10 C12A -44.9(3) . . . . ?
C6 C7 C10 C13A -107.2(2) . . . . ?
C8 C7 C10 C13A 71.3(2) . . . . ?
C6 C7 C10 C13B -45.0(7) . . . . ?
C8 C7 C10 C13B 133.5(7) . . . . ?
C6 C7 C10 C11B 69.6(7) . . . . ?
C8 C7 C10 C11B -111.9(7) . . . . ?
N2 C2 C14 C19 -170.61(15) . . . . ?
O1 C2 C14 C19 9.80(19) . . . . ?
N2 C2 C14 C15 9.6(2) . . . . ?
O1 C2 C14 C15 -169.97(12) . . . . ?
C19 C14 C15 C16 -0.2(2) . . . . ?
C2 C14 C15 C16 179.57(15) . . . . ?
C14 C15 C16 C17 0.4(3) . . . . ?
C15 C16 C17 C18 -0.1(3) . . . . ?
C16 C17 C18 C19 -0.4(3) . . . . ?
C17 C18 C19 C14 0.6(3) . . . . ?
C15 C14 C19 C18 -0.3(2) . . . . ?
C2 C14 C19 C18 179.92(14) . . . . ?

_refine_diff_density_max         0.185
_refine_diff_density_min         -0.201
_refine_diff_density_rms         0.047

####################################################################### 
# 
# 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_9_AUTO
_database_code_depnum_ccdc_archive 'CCDC 2241334'
loop_
_audit_author_name
_audit_author_address
'Muhammad Nawaz Tahir'
;University of Sargodha, Pakistan
Pakistan
;
_audit_update_record             
;
2023-10-06 deposited with the CCDC.	2023-10-23 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2019/2
_shelx_SHELXL_version_number     2019/2
_chemical_name_common            ?
_chemical_absolute_configuration .
_chemical_name_systematic        
2-[(4-Tertbutylphenylmethyl)sulfanyl]-5-(3,4,5-trimethoxyphenyl)-1,3,4-oxadiazole
_chemical_formula_moiety         'C22 H26 N2 O4 S'
_chemical_formula_sum            'C22 H26 N2 O4 S'
_chemical_formula_iupac          'C22 H26 N2 O4 S'
_chemical_formula_weight         414.51

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'

_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                   10.40660(10)
_cell_length_b                   24.9033(2)
_cell_length_c                   8.87920(10)
_cell_angle_alpha                90
_cell_angle_beta                 97.9360(10)
_cell_angle_gamma                90
_cell_volume                     2279.08(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4266
_cell_measurement_theta_min      4.290
_cell_measurement_theta_max      77.005
_cell_measurement_temperature    296(2)
_exptl_crystal_description       rod
_exptl_crystal_colour            'light yellow'
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.24
_exptl_crystal_density_diffrn    1.208
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             880
_exptl_absorpt_coefficient_mu    1.497
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.73a (Rigaku Oxford Diffraction, 2022)
Empirical absorption correctionusing spherical harmonics,
implimented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_correction_T_min  0.545
_exptl_absorpt_correction_T_max  0.615
_shelx_estimated_absorpt_T_min   0.615
_shelx_estimated_absorpt_T_max   0.774
_exptl_special_details           
;
;


_diffrn_ambient_temperature      296(2)
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC11 (RINC): quarter-chi single'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 8.16
_diffrn_reflns_number            31041
_diffrn_reflns_av_unetI/netI     0.0171
_diffrn_reflns_av_R_equivalents  0.0282
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -30
_diffrn_reflns_limit_k_max       30
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         4.290
_diffrn_reflns_theta_max         70.975
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_standards_number         0
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?

_refine_special_details          
;
Refinement of F² against ALL reflections. The weighted R-factor
wR and goodness of fit S are based on F², conventional
R-factors R are based on F, with F set to zero for
negative F². The threshold expression of F² >
σ(F²) is used only for calculating R-factors(gt) etc.
and is not relevant to the choice of reflections for refinement.
R-factors based on F² are statistically about twice as large
as those based on F, and R- factors based on ALL data will be
even larger.
;
_reflns_number_total             4391
_reflns_number_gt                4023
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0480
_refine_ls_R_factor_gt           0.0454
_refine_ls_wR_factor_ref         0.1372
_refine_ls_wR_factor_gt          0.1342
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_restrained_S_all      1.112
_refine_ls_number_reflns         4391
_refine_ls_number_parameters     286
_refine_ls_number_restraints     14
_refine_ls_hydrogen_treatment    constr
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0771P)²+0.4386P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_refine_ls_extinction_method     'SHELXL-2019/2 (Sheldrick 2019)'
_refine_ls_extinction_coef       0.0015(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_computing_data_collection       'APEX2 (Bruker, 2007)'
_computing_cell_refinement       'SAINT (Bruker, 2007)'
_computing_data_reduction        'SAINT (Bruker, 2007)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2019/2  (Sheldrick, 2019)'
_computing_molecular_graphics    
'ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 2009)'
_computing_publication_material  
;
WinGX (Farrugia, 1999) and PLATON (Spek, 2009)
;

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 0.65665(5) 0.37451(2) 0.60050(5) 0.07292(19) Uani 1 1 d . . . . .
O1 O 0.53307(11) 0.38893(4) 0.32221(12) 0.0584(3) Uani 1 1 d . . . . .
O2 O 0.27984(17) 0.51133(5) -0.07883(17) 0.0881(5) Uani 1 1 d . . . . .
O3 O 0.22596(15) 0.45039(6) -0.32929(16) 0.0855(4) Uani 1 1 d D . . . .
O4 O 0.30342(15) 0.34963(5) -0.33607(15) 0.0803(4) Uani 1 1 d . . . . .
N1 N 0.59366(16) 0.30476(5) 0.36516(16) 0.0636(4) Uani 1 1 d . . . . .
N2 N 0.53099(14) 0.30946(5) 0.21414(15) 0.0600(3) Uani 1 1 d . . . . .
C1 C 0.59207(16) 0.35213(6) 0.42158(18) 0.0558(4) Uani 1 1 d . . . . .
C2 C 0.49776(14) 0.35875(6) 0.19434(16) 0.0494(3) Uani 1 1 d . . . . .
C3 C 0.7459(2) 0.31393(7) 0.66696(19) 0.0673(4) Uani 1 1 d . . . . .
H3A H 0.686023 0.284476 0.674222 0.081 Uiso 1 1 calc R U . . .
H3B H 0.804805 0.303821 0.596183 0.081 Uiso 1 1 calc R U . . .
C4 C 0.82072(17) 0.32568(6) 0.82063(18) 0.0584(4) Uani 1 1 d . . . . .
C5 C 0.77040(16) 0.31192(6) 0.95153(19) 0.0572(4) Uani 1 1 d . . . . .
H5 H 0.689902 0.295177 0.944311 0.069 Uiso 1 1 calc R U . . .
C6 C 0.83845(16) 0.32278(7) 1.09270(18) 0.0583(4) Uani 1 1 d . . . . .
H6 H 0.802074 0.313355 1.178939 0.070 Uiso 1 1 calc R U . . .
C7 C 0.95850(16) 0.34713(8) 1.11045(19) 0.0628(4) Uani 1 1 d . . . . .
C8 C 1.00824(19) 0.36046(10) 0.9784(2) 0.0830(6) Uani 1 1 d . . . . .
H8 H 1.089394 0.376651 0.985843 0.100 Uiso 1 1 calc R U . . .
C9 C 0.9408(2) 0.35038(10) 0.8363(2) 0.0792(6) Uani 1 1 d . . . . .
H9 H 0.976482 0.360331 0.750001 0.095 Uiso 1 1 calc R U . . .
C10 C 1.02980(19) 0.35920(11) 1.2694(2) 0.0870(6) Uani 1 1 d D . . . .
C11A C 0.9536(4) 0.3992(2) 1.3473(5) 0.1239(15) Uani 0.699(3) 1 d D . P A 1
H11A H 0.865225 0.387334 1.341149 0.186 Uiso 0.699(3) 1 calc R U P A 1
H11B H 0.956089 0.433483 1.298461 0.186 Uiso 0.699(3) 1 calc R U P A 1
H11C H 0.990653 0.402293 1.452073 0.186 Uiso 0.699(3) 1 calc R U P A 1
C12A C 1.0243(4) 0.30595(19) 1.3759(4) 0.1105(13) Uani 0.699(3) 1 d D . P A 1
H12A H 0.935496 0.295739 1.377360 0.166 Uiso 0.699(3) 1 calc R U P A 1
H12B H 1.064139 0.313815 1.477567 0.166 Uiso 0.699(3) 1 calc R U P A 1
H12C H 1.069944 0.277012 1.335426 0.166 Uiso 0.699(3) 1 calc R U P A 1
C13A C 1.1714(3) 0.3708(2) 1.2779(5) 0.1075(16) Uani 0.699(3) 1 d D . P A 1
H13A H 1.211964 0.343139 1.225621 0.161 Uiso 0.699(3) 1 calc R U P A 1
H13B H 1.210110 0.371805 1.382495 0.161 Uiso 0.699(3) 1 calc R U P A 1
H13C H 1.183269 0.404853 1.231148 0.161 Uiso 0.699(3) 1 calc R U P A 1
C11B C 1.0476(10) 0.4246(3) 1.2561(10) 0.1239(15) Uani 0.301(3) 1 d D . P A 2
H11D H 1.120179 0.432209 1.203589 0.186 Uiso 0.301(3) 1 calc R U P A 2
H11E H 1.062505 0.439968 1.356171 0.186 Uiso 0.301(3) 1 calc R U P A 2
H11F H 0.970341 0.439848 1.200808 0.186 Uiso 0.301(3) 1 calc R U P A 2
C12B C 0.9660(9) 0.3486(5) 1.3952(8) 0.1105(13) Uani 0.301(3) 1 d D . P A 2
H12D H 0.892542 0.372013 1.393196 0.166 Uiso 0.301(3) 1 calc R U P A 2
H12E H 1.024558 0.354467 1.487132 0.166 Uiso 0.301(3) 1 calc R U P A 2
H12F H 0.937118 0.311908 1.391609 0.166 Uiso 0.301(3) 1 calc R U P A 2
C13B C 1.1655(7) 0.3394(4) 1.2657(13) 0.1075(16) Uani 0.301(3) 1 d D . P A 2
H13D H 1.193989 0.350073 1.171814 0.161 Uiso 0.301(3) 1 calc R U P A 2
H13E H 1.167103 0.300989 1.273512 0.161 Uiso 0.301(3) 1 calc R U P A 2
H13F H 1.222097 0.354599 1.349412 0.161 Uiso 0.301(3) 1 calc R U P A 2
C14 C 0.42968(14) 0.38393(6) 0.05818(17) 0.0507(3) Uani 1 1 d . . . . .
C15 C 0.39180(16) 0.43730(6) 0.06086(19) 0.0572(4) Uani 1 1 d . . . . .
H15 H 0.411511 0.457683 0.148771 0.069 Uiso 1 1 calc R U . . .
C16 C 0.32424(17) 0.45977(6) -0.0692(2) 0.0623(4) Uani 1 1 d . . . . .
C17 C 0.29682(17) 0.42940(7) -0.2016(2) 0.0620(4) Uani 1 1 d . . . . .
C18 C 0.33586(16) 0.37571(6) -0.20211(19) 0.0582(4) Uani 1 1 d . . . . .
C19 C 0.40213(15) 0.35304(6) -0.07198(18) 0.0550(4) Uani 1 1 d . . . . .
H19 H 0.428038 0.317292 -0.071794 0.066 Uiso 1 1 calc R U . . .
C20 C 0.2882(3) 0.54157(8) 0.0572(3) 0.0929(7) Uani 1 1 d . . . . .
H20A H 0.248126 0.575979 0.035983 0.139 Uiso 1 1 calc R U . . .
H20B H 0.377675 0.546469 0.098266 0.139 Uiso 1 1 calc R U . . .
H20C H 0.244347 0.522776 0.129641 0.139 Uiso 1 1 calc R U . . .
C21A C 0.2908(12) 0.4873(3) -0.4139(16) 0.116(2) Uani 0.699(3) 1 d D . P A 1
H21A H 0.325925 0.515995 -0.348707 0.175 Uiso 0.699(3) 1 calc R U P A 1
H21B H 0.230597 0.501603 -0.495655 0.175 Uiso 0.699(3) 1 calc R U P A 1
H21C H 0.359900 0.469237 -0.454649 0.175 Uiso 0.699(3) 1 calc R U P A 1
C21B C 0.314(3) 0.4748(10) -0.424(4) 0.116(2) Uani 0.301(3) 1 d D . P A 2
H21D H 0.370504 0.499367 -0.363453 0.175 Uiso 0.301(3) 1 calc R U P A 2
H21E H 0.264266 0.493885 -0.506053 0.175 Uiso 0.301(3) 1 calc R U P A 2
H21F H 0.364116 0.447335 -0.463584 0.175 Uiso 0.301(3) 1 calc R U P A 2
C22 C 0.3413(3) 0.29485(8) -0.3419(3) 0.0967(8) Uani 1 1 d . . . . .
H22A H 0.323669 0.282143 -0.444796 0.145 Uiso 1 1 calc R U . . .
H22B H 0.293294 0.273779 -0.278310 0.145 Uiso 1 1 calc R U . . .
H22C H 0.432395 0.291657 -0.306655 0.145 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
S1 C1 1.7295(16) . ?
S1 C3 1.8262(18) . ?
O1 C1 1.3586(18) . ?
O1 C2 1.3690(18) . ?
O2 C16 1.3634(19) . ?
O2 C20 1.416(3) . ?
O3 C17 1.368(2) . ?
O3 C21A 1.415(5) . ?
O3 C21B 1.455(10) . ?
O4 C18 1.356(2) . ?
O4 C22 1.423(2) . ?
N1 C1 1.283(2) . ?
N1 N2 1.4127(19) . ?
N2 C2 1.281(2) . ?
C2 C14 1.456(2) . ?
C3 C4 1.504(2) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C4 C5 1.382(2) . ?
C4 C9 1.382(3) . ?
C5 C6 1.379(2) . ?
C5 H5 0.9300 . ?
C6 C7 1.378(2) . ?
C6 H6 0.9300 . ?
C7 C8 1.385(3) . ?
C7 C10 1.531(2) . ?
C8 C9 1.380(3) . ?
C8 H8 0.9300 . ?
C9 H9 0.9300 . ?
C10 C12B 1.402(7) . ?
C10 C13A 1.493(4) . ?
C10 C13B 1.500(8) . ?
C10 C11A 1.500(4) . ?
C10 C12A 1.635(4) . ?
C10 C11B 1.646(7) . ?
C11A H11A 0.9600 . ?
C11A H11B 0.9600 . ?
C11A H11C 0.9600 . ?
C12A H12A 0.9600 . ?
C12A H12B 0.9600 . ?
C12A H12C 0.9600 . ?
C13A H13A 0.9600 . ?
C13A H13B 0.9600 . ?
C13A H13C 0.9600 . ?
C11B H11D 0.9600 . ?
C11B H11E 0.9600 . ?
C11B H11F 0.9600 . ?
C12B H12D 0.9600 . ?
C12B H12E 0.9600 . ?
C12B H12F 0.9600 . ?
C13B H13D 0.9600 . ?
C13B H13E 0.9600 . ?
C13B H13F 0.9600 . ?
C14 C19 1.385(2) . ?
C14 C15 1.387(2) . ?
C15 C16 1.385(2) . ?
C15 H15 0.9300 . ?
C16 C17 1.394(2) . ?
C17 C18 1.398(2) . ?
C18 C19 1.382(2) . ?
C19 H19 0.9300 . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
C21A H21A 0.9600 . ?
C21A H21B 0.9600 . ?
C21A H21C 0.9600 . ?
C21B H21D 0.9600 . ?
C21B H21E 0.9600 . ?
C21B H21F 0.9600 . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 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
C1 S1 C3 98.42(8) . . ?
C1 O1 C2 102.34(12) . . ?
C16 O2 C20 117.85(15) . . ?
C17 O3 C21A 116.5(7) . . ?
C17 O3 C21B 109.1(17) . . ?
C18 O4 C22 117.04(14) . . ?
C1 N1 N2 105.39(12) . . ?
C2 N2 N1 106.87(13) . . ?
N1 C1 O1 113.31(14) . . ?
N1 C1 S1 129.10(12) . . ?
O1 C1 S1 117.56(11) . . ?
N2 C2 O1 112.08(13) . . ?
N2 C2 C14 128.17(14) . . ?
O1 C2 C14 119.75(13) . . ?
C4 C3 S1 108.00(12) . . ?
C4 C3 H3A 110.1 . . ?
S1 C3 H3A 110.1 . . ?
C4 C3 H3B 110.1 . . ?
S1 C3 H3B 110.1 . . ?
H3A C3 H3B 108.4 . . ?
C5 C4 C9 117.90(16) . . ?
C5 C4 C3 120.39(16) . . ?
C9 C4 C3 121.71(16) . . ?
C6 C5 C4 120.61(15) . . ?
C6 C5 H5 119.7 . . ?
C4 C5 H5 119.7 . . ?
C7 C6 C5 122.28(15) . . ?
C7 C6 H6 118.9 . . ?
C5 C6 H6 118.9 . . ?
C6 C7 C8 116.57(16) . . ?
C6 C7 C10 120.55(16) . . ?
C8 C7 C10 122.87(16) . . ?
C9 C8 C7 121.87(18) . . ?
C9 C8 H8 119.1 . . ?
C7 C8 H8 119.1 . . ?
C8 C9 C4 120.76(17) . . ?
C8 C9 H9 119.6 . . ?
C4 C9 H9 119.6 . . ?
C12B C10 C13B 120.4(6) . . ?
C13A C10 C11A 115.4(3) . . ?
C12B C10 C7 118.4(4) . . ?
C13A C10 C7 115.7(2) . . ?
C13B C10 C7 104.7(4) . . ?
C11A C10 C7 109.6(2) . . ?
C13A C10 C12A 103.9(3) . . ?
C11A C10 C12A 102.0(3) . . ?
C7 C10 C12A 108.8(2) . . ?
C12B C10 C11B 108.3(6) . . ?
C13B C10 C11B 102.0(5) . . ?
C7 C10 C11B 100.0(3) . . ?
C10 C11A H11A 109.5 . . ?
C10 C11A H11B 109.5 . . ?
H11A C11A H11B 109.5 . . ?
C10 C11A H11C 109.5 . . ?
H11A C11A H11C 109.5 . . ?
H11B C11A H11C 109.5 . . ?
C10 C12A H12A 109.5 . . ?
C10 C12A H12B 109.5 . . ?
H12A C12A H12B 109.5 . . ?
C10 C12A H12C 109.5 . . ?
H12A C12A H12C 109.5 . . ?
H12B C12A H12C 109.5 . . ?
C10 C13A H13A 109.5 . . ?
C10 C13A H13B 109.5 . . ?
H13A C13A H13B 109.5 . . ?
C10 C13A H13C 109.5 . . ?
H13A C13A H13C 109.5 . . ?
H13B C13A H13C 109.5 . . ?
C10 C11B H11D 109.5 . . ?
C10 C11B H11E 109.5 . . ?
H11D C11B H11E 109.5 . . ?
C10 C11B H11F 109.5 . . ?
H11D C11B H11F 109.5 . . ?
H11E C11B H11F 109.5 . . ?
C10 C12B H12D 109.5 . . ?
C10 C12B H12E 109.5 . . ?
H12D C12B H12E 109.5 . . ?
C10 C12B H12F 109.5 . . ?
H12D C12B H12F 109.5 . . ?
H12E C12B H12F 109.5 . . ?
C10 C13B H13D 109.5 . . ?
C10 C13B H13E 109.5 . . ?
H13D C13B H13E 109.5 . . ?
C10 C13B H13F 109.5 . . ?
H13D C13B H13F 109.5 . . ?
H13E C13B H13F 109.5 . . ?
C19 C14 C15 121.33(14) . . ?
C19 C14 C2 118.32(13) . . ?
C15 C14 C2 120.34(14) . . ?
C16 C15 C14 119.05(15) . . ?
C16 C15 H15 120.5 . . ?
C14 C15 H15 120.5 . . ?
O2 C16 C15 124.17(16) . . ?
O2 C16 C17 115.47(15) . . ?
C15 C16 C17 120.36(15) . . ?
O3 C17 C16 121.04(15) . . ?
O3 C17 C18 119.12(15) . . ?
C16 C17 C18 119.74(15) . . ?
O4 C18 C19 124.94(14) . . ?
O4 C18 C17 115.06(14) . . ?
C19 C18 C17 120.00(15) . . ?
C18 C19 C14 119.51(14) . . ?
C18 C19 H19 120.2 . . ?
C14 C19 H19 120.2 . . ?
O2 C20 H20A 109.5 . . ?
O2 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
O2 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
O3 C21A H21A 109.5 . . ?
O3 C21A H21B 109.5 . . ?
H21A C21A H21B 109.5 . . ?
O3 C21A H21C 109.5 . . ?
H21A C21A H21C 109.5 . . ?
H21B C21A H21C 109.5 . . ?
O3 C21B H21D 109.5 . . ?
O3 C21B H21E 109.5 . . ?
H21D C21B H21E 109.5 . . ?
O3 C21B H21F 109.5 . . ?
H21D C21B H21F 109.5 . . ?
H21E C21B H21F 109.5 . . ?
O4 C22 H22A 109.5 . . ?
O4 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
O4 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 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
C1 N1 N2 C2 -0.12(18) . . . . ?
N2 N1 C1 O1 0.3(2) . . . . ?
N2 N1 C1 S1 -178.11(13) . . . . ?
C2 O1 C1 N1 -0.31(19) . . . . ?
C2 O1 C1 S1 178.28(11) . . . . ?
C3 S1 C1 N1 8.42(19) . . . . ?
C3 S1 C1 O1 -169.91(13) . . . . ?
N1 N2 C2 O1 -0.08(18) . . . . ?
N1 N2 C2 C14 -179.61(15) . . . . ?
C1 O1 C2 N2 0.23(17) . . . . ?
C1 O1 C2 C14 179.80(13) . . . . ?
C1 S1 C3 C4 175.56(13) . . . . ?
S1 C3 C4 C5 95.98(17) . . . . ?
S1 C3 C4 C9 -83.9(2) . . . . ?
C9 C4 C5 C6 0.1(3) . . . . ?
C3 C4 C5 C6 -179.76(15) . . . . ?
C4 C5 C6 C7 -0.5(3) . . . . ?
C5 C6 C7 C8 0.1(3) . . . . ?
C5 C6 C7 C10 179.09(18) . . . . ?
C6 C7 C8 C9 0.6(3) . . . . ?
C10 C7 C8 C9 -178.4(2) . . . . ?
C7 C8 C9 C4 -0.9(4) . . . . ?
C5 C4 C9 C8 0.5(3) . . . . ?
C3 C4 C9 C8 -179.5(2) . . . . ?
C6 C7 C10 C12B -4.7(7) . . . . ?
C8 C7 C10 C12B 174.2(6) . . . . ?
C6 C7 C10 C13A 163.3(3) . . . . ?
C8 C7 C10 C13A -17.8(4) . . . . ?
C6 C7 C10 C13B 132.8(5) . . . . ?
C8 C7 C10 C13B -48.3(5) . . . . ?
C6 C7 C10 C11A -64.1(3) . . . . ?
C8 C7 C10 C11A 114.8(3) . . . . ?
C6 C7 C10 C12A 46.7(3) . . . . ?
C8 C7 C10 C12A -134.4(3) . . . . ?
C6 C7 C10 C11B -121.9(4) . . . . ?
C8 C7 C10 C11B 57.0(5) . . . . ?
N2 C2 C14 C19 -4.3(2) . . . . ?
O1 C2 C14 C19 176.23(13) . . . . ?
N2 C2 C14 C15 174.60(16) . . . . ?
O1 C2 C14 C15 -4.9(2) . . . . ?
C19 C14 C15 C16 0.5(2) . . . . ?
C2 C14 C15 C16 -178.33(15) . . . . ?
C20 O2 C16 C15 -8.7(3) . . . . ?
C20 O2 C16 C17 171.0(2) . . . . ?
C14 C15 C16 O2 178.55(17) . . . . ?
C14 C15 C16 C17 -1.1(3) . . . . ?
C21A O3 C17 C16 75.5(5) . . . . ?
C21B O3 C17 C16 91.3(13) . . . . ?
C21A O3 C17 C18 -108.0(5) . . . . ?
C21B O3 C17 C18 -92.3(13) . . . . ?
O2 C16 C17 O3 -2.2(3) . . . . ?
C15 C16 C17 O3 177.51(17) . . . . ?
O2 C16 C17 C18 -178.61(17) . . . . ?
C15 C16 C17 C18 1.1(3) . . . . ?
C22 O4 C18 C19 -0.2(3) . . . . ?
C22 O4 C18 C17 180.0(2) . . . . ?
O3 C17 C18 O4 2.9(3) . . . . ?
C16 C17 C18 O4 179.42(17) . . . . ?
O3 C17 C18 C19 -176.91(16) . . . . ?
C16 C17 C18 C19 -0.4(3) . . . . ?
O4 C18 C19 C14 179.97(16) . . . . ?
C17 C18 C19 C14 -0.2(3) . . . . ?
C15 C14 C19 C18 0.1(2) . . . . ?
C2 C14 C19 C18 179.01(14) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
C21A^a H21A^a O2 0.96 2.51 3.052(13) 115.7 . yes

_refine_diff_density_max         0.312
_refine_diff_density_min         -0.265
_refine_diff_density_rms         0.034

