# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2021

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_A31P
_database_code_depnum_ccdc_archive 'CCDC 1009301'
loop_
_audit_author_name
_audit_author_address
'Muhammad Ashfaq'
;University of Sargodha
Pakistan
;
_audit_update_record             
;
2021-02-05 deposited with the CCDC.	2021-03-09 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_absolute_configuration .
_chemical_name_systematic        
;
Ethyl 2-[5-(4-bromophenyl)-3-(4-chlorophenyl)-4,5-dihydro-1H-pyrazol-1-yl]-
1,3-thiazole-4-carboxylate
;
_chemical_formula_moiety         'C21 H17 Br Cl N3 O2 S'
_chemical_formula_sum            'C21 H17 Br Cl N3 O2 S'
_chemical_formula_iupac          'C21 H17 Br Cl N3 O2 S'
_chemical_formula_weight         490.80

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'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           1
_space_group_name_H-M_alt        'P 1'
_space_group_name_Hall           'P 1'

_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'

_cell_length_a                   4.7441(4)
_cell_length_b                   9.5883(9)
_cell_length_c                   12.0770(11)
_cell_angle_alpha                73.421(5)
_cell_angle_beta                 89.483(5)
_cell_angle_gamma                86.045(6)
_cell_volume                     525.23(8)
_cell_formula_units_Z            1
_cell_measurement_reflns_used    3367
_cell_measurement_theta_min      2.222
_cell_measurement_theta_max      27.502
_cell_measurement_temperature    296(2)
_exptl_crystal_description       needle
_exptl_crystal_colour            white
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.16
_exptl_crystal_density_diffrn    1.552
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             248
_exptl_absorpt_coefficient_mu    2.206
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2005)'
_exptl_absorpt_correction_T_min  0.668
_exptl_absorpt_correction_T_max  0.746
_shelx_estimated_absorpt_T_min   0.472
_shelx_estimated_absorpt_T_max   0.719
_exptl_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.

;


_diffrn_ambient_temperature      296(2)
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker Kappa APEXII CCD'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 7.72
_diffrn_reflns_number            8109
_diffrn_reflns_av_unetI/netI     0.0417
_diffrn_reflns_av_R_equivalents  0.0268
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.222
_diffrn_reflns_theta_max         27.502
_diffrn_reflns_theta_full        27.502
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measured_fraction_theta_full 0.986
_diffrn_standards_number         0
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_reflns_Friedel_coverage         1.000
_reflns_Friedel_fraction_max     0.986
_reflns_Friedel_fraction_full    0.993

_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             4306
_reflns_number_gt                3367
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0499
_refine_ls_R_factor_gt           0.0346
_refine_ls_wR_factor_ref         0.0766
_refine_ls_wR_factor_gt          0.0713
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_restrained_S_all      1.032
_refine_ls_number_reflns         4306
_refine_ls_number_parameters     263
_refine_ls_number_restraints     3
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0336P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_abs_structure_details 
;
 Refined as a perfect inversion twin.
;
_refine_ls_abs_structure_Flack   0.5

_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-2018/3  (Sheldrick, 2015)'
_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
Br1 Br 1.13588(10) 0.09484(6) 1.34405(5) 0.1044(3) Uani 1 1 d . . . . .
Cl1 Cl 1.7672(3) 0.73600(16) 0.30733(12) 0.0823(4) Uani 1 1 d . . . . .
S1 S 0.9174(2) -0.07729(11) 0.64916(9) 0.0512(3) Uani 1 1 d . . . . .
O1 O 0.2707(6) -0.2551(3) 0.9610(3) 0.0590(8) Uani 1 1 d . . . . .
O2 O 0.3531(7) -0.4162(3) 0.8595(3) 0.0681(8) Uani 1 1 d . . . . .
N1 N 0.6521(6) -0.0734(3) 0.8378(3) 0.0418(7) Uani 1 1 d . . . . .
N2 N 0.9447(7) 0.1207(4) 0.7666(3) 0.0482(8) Uani 1 1 d . . . . .
N3 N 1.1105(6) 0.1878(3) 0.6741(3) 0.0443(8) Uani 1 1 d . . . . .
C1 C 0.2394(12) -0.4489(6) 1.1378(5) 0.0855(16) Uani 1 1 d . . . . .
H1A H 0.374510 -0.511579 1.111864 0.128 Uiso 1 1 calc R U . . .
H1B H 0.111659 -0.507048 1.190679 0.128 Uiso 1 1 calc R U . . .
H1C H 0.336275 -0.390790 1.176112 0.128 Uiso 1 1 calc R U . . .
C2 C 0.0785(10) -0.3523(6) 1.0375(4) 0.0698(13) Uani 1 1 d . . . . .
H2A H -0.009518 -0.410532 0.995551 0.084 Uiso 1 1 calc R U . . .
H2B H -0.069275 -0.294715 1.063904 0.084 Uiso 1 1 calc R U . . .
C3 C 0.3937(8) -0.3011(5) 0.8774(3) 0.0468(10) Uani 1 1 d . . . . .
C4 C 0.5839(8) -0.1957(4) 0.8070(3) 0.0397(8) Uani 1 1 d . . . . .
C5 C 0.7066(8) -0.2158(4) 0.7117(4) 0.0466(9) Uani 1 1 d . . . . .
H5 H 0.680520 -0.294587 0.683336 0.056 Uiso 1 1 calc R U . . .
C6 C 0.8274(7) -0.0038(4) 0.7617(3) 0.0396(8) Uani 1 1 d . . . . .
C7 C 1.1153(8) 0.3248(4) 0.6690(3) 0.0427(9) Uani 1 1 d . . . . .
C8 C 0.9363(8) 0.3671(4) 0.7589(4) 0.0474(9) Uani 1 1 d . . . . .
H8A H 0.784855 0.438744 0.723440 0.057 Uiso 1 1 calc R U . . .
H8B H 1.048881 0.406664 0.807915 0.057 Uiso 1 1 calc R U . . .
C9 C 0.8189(8) 0.2230(4) 0.8280(3) 0.0431(9) Uani 1 1 d . . . . .
H9 H 0.612786 0.230376 0.819126 0.052 Uiso 1 1 calc R U . . .
C10 C 0.8961(8) 0.1798(4) 0.9550(3) 0.0426(8) Uani 1 1 d . . . . .
C11 C 1.1072(9) 0.0763(4) 1.0051(4) 0.0551(11) Uani 1 1 d . . . . .
H11 H 1.204599 0.024362 0.960765 0.066 Uiso 1 1 calc R U . . .
C12 C 1.1770(11) 0.0483(5) 1.1208(4) 0.0676(13) Uani 1 1 d . . . . .
H12 H 1.320010 -0.022244 1.153956 0.081 Uiso 1 1 calc R U . . .
C13 C 1.0347(10) 0.1249(5) 1.1861(4) 0.0606(12) Uani 1 1 d . . . . .
C14 C 0.8200(11) 0.2272(6) 1.1400(4) 0.0690(13) Uani 1 1 d . . . . .
H14 H 0.721787 0.277711 1.185171 0.083 Uiso 1 1 calc R U . . .
C15 C 0.7524(11) 0.2538(6) 1.0231(4) 0.0633(12) Uani 1 1 d . . . . .
H15 H 0.606936 0.323027 0.990411 0.076 Uiso 1 1 calc R U . . .
C16 C 1.2826(8) 0.4226(4) 0.5817(3) 0.0435(9) Uani 1 1 d . . . . .
C17 C 1.4642(9) 0.3713(5) 0.5079(4) 0.0543(11) Uani 1 1 d . . . . .
H17 H 1.482647 0.272063 0.514625 0.065 Uiso 1 1 calc R U . . .
C18 C 1.6162(10) 0.4661(6) 0.4254(4) 0.0604(12) Uani 1 1 d . . . . .
H18 H 1.740340 0.430714 0.378072 0.072 Uiso 1 1 calc R U . . .
C19 C 1.5829(9) 0.6134(5) 0.4135(4) 0.0546(11) Uani 1 1 d . . . . .
C20 C 1.4087(9) 0.6676(5) 0.4850(4) 0.0582(11) Uani 1 1 d . . . . .
H20 H 1.389714 0.767232 0.476615 0.070 Uiso 1 1 calc R U . . .
C21 C 1.2603(9) 0.5711(5) 0.5704(4) 0.0530(10) Uani 1 1 d . . . . .
H21 H 1.145224 0.606692 0.620372 0.064 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
Br1 C13 1.907(4) . ?
Cl1 C19 1.747(4) . ?
S1 C5 1.712(4) . ?
S1 C6 1.738(4) . ?
O1 C3 1.327(5) . ?
O1 C2 1.471(6) . ?
O2 C3 1.212(5) . ?
N1 C6 1.302(5) . ?
N1 C4 1.386(5) . ?
N2 C6 1.367(5) . ?
N2 N3 1.387(5) . ?
N2 C9 1.482(5) . ?
N3 C7 1.299(5) . ?
C1 C2 1.479(7) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C3 C4 1.476(6) . ?
C4 C5 1.342(5) . ?
C5 H5 0.9300 . ?
C7 C16 1.464(5) . ?
C7 C8 1.501(6) . ?
C8 C9 1.535(6) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 C10 1.512(5) . ?
C9 H9 0.9800 . ?
C10 C11 1.373(5) . ?
C10 C15 1.378(6) . ?
C11 C12 1.384(6) . ?
C11 H11 0.9300 . ?
C12 C13 1.367(6) . ?
C12 H12 0.9300 . ?
C13 C14 1.368(7) . ?
C14 C15 1.397(7) . ?
C14 H14 0.9300 . ?
C15 H15 0.9300 . ?
C16 C21 1.388(6) . ?
C16 C17 1.398(5) . ?
C17 C18 1.378(6) . ?
C17 H17 0.9300 . ?
C18 C19 1.377(6) . ?
C18 H18 0.9300 . ?
C19 C20 1.372(6) . ?
C20 C21 1.396(6) . ?
C20 H20 0.9300 . ?
C21 H21 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
C5 S1 C6 87.50(19) . . ?
C3 O1 C2 117.4(4) . . ?
C6 N1 C4 107.9(3) . . ?
C6 N2 N3 116.8(3) . . ?
C6 N2 C9 124.3(3) . . ?
N3 N2 C9 113.1(3) . . ?
C7 N3 N2 108.6(3) . . ?
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
O1 C2 C1 109.5(4) . . ?
O1 C2 H2A 109.8 . . ?
C1 C2 H2A 109.8 . . ?
O1 C2 H2B 109.8 . . ?
C1 C2 H2B 109.8 . . ?
H2A C2 H2B 108.2 . . ?
O2 C3 O1 124.0(4) . . ?
O2 C3 C4 123.3(4) . . ?
O1 C3 C4 112.7(4) . . ?
C5 C4 N1 116.5(3) . . ?
C5 C4 C3 121.6(4) . . ?
N1 C4 C3 121.9(3) . . ?
C4 C5 S1 111.1(3) . . ?
C4 C5 H5 124.5 . . ?
S1 C5 H5 124.5 . . ?
N1 C6 N2 123.9(3) . . ?
N1 C6 S1 116.9(3) . . ?
N2 C6 S1 119.1(3) . . ?
N3 C7 C16 120.9(4) . . ?
N3 C7 C8 113.3(4) . . ?
C16 C7 C8 125.8(3) . . ?
C7 C8 C9 103.6(3) . . ?
C7 C8 H8A 111.0 . . ?
C9 C8 H8A 111.0 . . ?
C7 C8 H8B 111.0 . . ?
C9 C8 H8B 111.0 . . ?
H8A C8 H8B 109.0 . . ?
N2 C9 C10 113.4(3) . . ?
N2 C9 C8 101.5(3) . . ?
C10 C9 C8 113.4(3) . . ?
N2 C9 H9 109.4 . . ?
C10 C9 H9 109.4 . . ?
C8 C9 H9 109.4 . . ?
C11 C10 C15 118.4(4) . . ?
C11 C10 C9 124.1(3) . . ?
C15 C10 C9 117.5(4) . . ?
C10 C11 C12 120.9(4) . . ?
C10 C11 H11 119.6 . . ?
C12 C11 H11 119.6 . . ?
C13 C12 C11 119.6(4) . . ?
C13 C12 H12 120.2 . . ?
C11 C12 H12 120.2 . . ?
C12 C13 C14 121.3(4) . . ?
C12 C13 Br1 120.7(3) . . ?
C14 C13 Br1 117.9(4) . . ?
C13 C14 C15 118.2(4) . . ?
C13 C14 H14 120.9 . . ?
C15 C14 H14 120.9 . . ?
C10 C15 C14 121.6(4) . . ?
C10 C15 H15 119.2 . . ?
C14 C15 H15 119.2 . . ?
C21 C16 C17 118.4(4) . . ?
C21 C16 C7 119.5(4) . . ?
C17 C16 C7 122.0(4) . . ?
C18 C17 C16 120.8(4) . . ?
C18 C17 H17 119.6 . . ?
C16 C17 H17 119.6 . . ?
C19 C18 C17 119.5(4) . . ?
C19 C18 H18 120.3 . . ?
C17 C18 H18 120.3 . . ?
C20 C19 C18 121.3(4) . . ?
C20 C19 Cl1 118.4(4) . . ?
C18 C19 Cl1 120.3(4) . . ?
C19 C20 C21 119.1(4) . . ?
C19 C20 H20 120.4 . . ?
C21 C20 H20 120.4 . . ?
C16 C21 C20 120.8(4) . . ?
C16 C21 H21 119.6 . . ?
C20 C21 H21 119.6 . . ?

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
C6 N2 N3 C7 156.1(3) . . . . ?
C9 N2 N3 C7 1.8(4) . . . . ?
C3 O1 C2 C1 90.5(5) . . . . ?
C2 O1 C3 O2 1.3(6) . . . . ?
C2 O1 C3 C4 -179.3(3) . . . . ?
C6 N1 C4 C5 0.4(4) . . . . ?
C6 N1 C4 C3 178.5(3) . . . . ?
O2 C3 C4 C5 5.8(6) . . . . ?
O1 C3 C4 C5 -173.5(3) . . . . ?
O2 C3 C4 N1 -172.1(3) . . . . ?
O1 C3 C4 N1 8.5(5) . . . . ?
N1 C4 C5 S1 -1.4(4) . . . . ?
C3 C4 C5 S1 -179.4(3) . . . . ?
C6 S1 C5 C4 1.4(3) . . . . ?
C4 N1 C6 N2 -178.3(3) . . . . ?
C4 N1 C6 S1 0.8(4) . . . . ?
N3 N2 C6 N1 -175.2(3) . . . . ?
C9 N2 C6 N1 -24.0(6) . . . . ?
N3 N2 C6 S1 5.7(4) . . . . ?
C9 N2 C6 S1 156.9(3) . . . . ?
C5 S1 C6 N1 -1.3(3) . . . . ?
C5 S1 C6 N2 177.8(3) . . . . ?
N2 N3 C7 C16 177.9(3) . . . . ?
N2 N3 C7 C8 -2.3(4) . . . . ?
N3 C7 C8 C9 1.9(4) . . . . ?
C16 C7 C8 C9 -178.3(3) . . . . ?
C6 N2 C9 C10 85.4(4) . . . . ?
N3 N2 C9 C10 -122.5(3) . . . . ?
C6 N2 C9 C8 -152.7(3) . . . . ?
N3 N2 C9 C8 -0.5(4) . . . . ?
C7 C8 C9 N2 -0.7(4) . . . . ?
C7 C8 C9 C10 121.3(3) . . . . ?
N2 C9 C10 C11 13.5(5) . . . . ?
C8 C9 C10 C11 -101.6(4) . . . . ?
N2 C9 C10 C15 -169.4(4) . . . . ?
C8 C9 C10 C15 75.6(5) . . . . ?
C15 C10 C11 C12 -0.9(7) . . . . ?
C9 C10 C11 C12 176.2(4) . . . . ?
C10 C11 C12 C13 -0.2(7) . . . . ?
C11 C12 C13 C14 1.3(8) . . . . ?
C11 C12 C13 Br1 -177.4(4) . . . . ?
C12 C13 C14 C15 -1.1(8) . . . . ?
Br1 C13 C14 C15 177.5(4) . . . . ?
C11 C10 C15 C14 1.0(7) . . . . ?
C9 C10 C15 C14 -176.3(4) . . . . ?
C13 C14 C15 C10 0.0(8) . . . . ?
N3 C7 C16 C21 173.2(3) . . . . ?
C8 C7 C16 C21 -6.6(6) . . . . ?
N3 C7 C16 C17 -6.3(5) . . . . ?
C8 C7 C16 C17 173.9(4) . . . . ?
C21 C16 C17 C18 -0.4(6) . . . . ?
C7 C16 C17 C18 179.1(4) . . . . ?
C16 C17 C18 C19 -1.7(7) . . . . ?
C17 C18 C19 C20 2.4(7) . . . . ?
C17 C18 C19 Cl1 -178.6(4) . . . . ?
C18 C19 C20 C21 -0.8(7) . . . . ?
Cl1 C19 C20 C21 -179.9(3) . . . . ?
C17 C16 C21 C20 2.1(6) . . . . ?
C7 C16 C21 C20 -177.5(4) . . . . ?
C19 C20 C21 C16 -1.5(6) . . . . ?

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
C8 H8B O2 0.97 2.51 3.428(5) 157.3 1_665 yes

_refine_diff_density_max         0.168
_refine_diff_density_min         -0.302
_refine_diff_density_rms         0.048


####################################################################### 
# 
# 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_B24
_database_code_depnum_ccdc_archive 'CCDC 1009302'
loop_
_audit_author_name
_audit_author_address
'Muhammad Ashfaq'
;University of Sargodha
Pakistan
;
_audit_update_record             
;
2021-02-05 deposited with the CCDC.	2021-03-09 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_absolute_configuration .
_chemical_name_systematic        
;
2-(5-(4-Chlorophenyl)-3-phenyl-4,5-dihydro-1H-pyrazol-1-yl)-N'-[(E)-(2-hydroxy
-3-methoxyphenyl)methylidene]-1,3-thiazole-4-carbohydrazide
;
_chemical_formula_moiety         'C27 H22 Cl N5 O3 S'
_chemical_formula_sum            'C27 H22 Cl N5 O3 S'
_chemical_formula_iupac          'C27 H22 Cl N5 O3 S'
_chemical_formula_weight         532.00

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      orthorhombic
_space_group_IT_number           29
_space_group_name_H-M_alt        'P c a 21'
_space_group_name_Hall           'P 2c -2ac'

_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+1/2, y, z+1/2'
'x+1/2, -y, z'

_cell_length_a                   23.994(4)
_cell_length_b                   5.0580(9)
_cell_length_c                   20.359(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2470.8(7)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2853
_cell_measurement_theta_min      1.697
_cell_measurement_theta_max      27.481
_cell_measurement_temperature    296(2)
_exptl_crystal_description       needle
_exptl_crystal_colour            'light yellow'
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.16
_exptl_crystal_density_diffrn    1.430
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1104
_exptl_absorpt_coefficient_mu    0.280
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2005)'
_exptl_absorpt_correction_T_min  0.672
_exptl_absorpt_correction_T_max  0.746
_shelx_estimated_absorpt_T_min   0.891
_shelx_estimated_absorpt_T_max   0.957
_exptl_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.

;


_diffrn_ambient_temperature      296(2)
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker Kappa APEXII CCD'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 7.72
_diffrn_reflns_number            20066
_diffrn_reflns_av_unetI/netI     0.1189
_diffrn_reflns_av_R_equivalents  0.0887
_diffrn_reflns_limit_h_min       -30
_diffrn_reflns_limit_h_max       31
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         1.697
_diffrn_reflns_theta_max         27.481
_diffrn_reflns_theta_full        27.481
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.996
_diffrn_standards_number         0
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_reflns_Friedel_coverage         0.911
_reflns_Friedel_fraction_max     0.961
_reflns_Friedel_fraction_full    0.985

_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             5563
_reflns_number_gt                2853
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.1335
_refine_ls_R_factor_gt           0.0465
_refine_ls_wR_factor_ref         0.0779
_refine_ls_wR_factor_gt          0.0628
_refine_ls_goodness_of_fit_ref   0.915
_refine_ls_restrained_S_all      0.915
_refine_ls_number_reflns         5563
_refine_ls_number_parameters     336
_refine_ls_number_restraints     1
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0194P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_abs_structure_details 
;
 Flack x determined using 984 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.06(5)

_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-2018/3  (Sheldrick, 2015)'
_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
Cl1 Cl 0.33007(6) 1.5398(4) 0.33144(7) 0.0914(6) Uani 1 1 d . . . . .
S1 S 0.28371(4) 1.2299(2) -0.07110(6) 0.0462(3) Uani 1 1 d . . . . .
O1 O 0.15388(12) 0.6286(7) -0.00749(17) 0.0652(10) Uani 1 1 d . . . . .
O2 O 0.09157(13) 0.0325(8) 0.12068(17) 0.0675(11) Uani 1 1 d . . . . .
H2A H 0.108993 0.155235 0.104208 0.101 Uiso 1 1 calc R U . . .
O3 O 0.04270(13) -0.3374(7) 0.18906(19) 0.0725(11) Uani 1 1 d . . . . .
N1 N 0.39090(14) 1.3873(7) -0.02539(17) 0.0428(10) Uani 1 1 d . . . . .
N2 N 0.36780(14) 1.1892(8) 0.01342(17) 0.0456(10) Uani 1 1 d . . . . .
N3 N 0.28857(14) 0.9162(7) 0.03015(16) 0.0387(9) Uani 1 1 d . . . . .
N4 N 0.21308(14) 0.5488(8) 0.07661(19) 0.0483(10) Uani 1 1 d . . . . .
H4A H 0.244062 0.592683 0.094839 0.058 Uiso 1 1 calc R U . . .
N5 N 0.18075(15) 0.3502(8) 0.1049(2) 0.0465(10) Uani 1 1 d . . . . .
C1 C 0.40016(19) 1.0997(10) 0.1918(2) 0.0614(14) Uani 1 1 d . . . . .
H1 H 0.423355 0.952599 0.189932 0.074 Uiso 1 1 calc R U . . .
C2 C 0.3832(2) 1.1965(12) 0.2524(2) 0.0697(16) Uani 1 1 d . . . . .
H2 H 0.394268 1.112326 0.290886 0.084 Uiso 1 1 calc R U . . .
C3 C 0.35055(19) 1.4142(11) 0.2551(2) 0.0530(14) Uani 1 1 d . . . . .
C4 C 0.33398(17) 1.5403(10) 0.1984(3) 0.0587(14) Uani 1 1 d . . . . .
H4 H 0.311788 1.690740 0.200722 0.070 Uiso 1 1 calc R U . . .
C5 C 0.35045(17) 1.4422(9) 0.1381(2) 0.0440(12) Uani 1 1 d . . . . .
H5 H 0.339431 1.527854 0.099834 0.053 Uiso 1 1 calc R U . . .
C6 C 0.38302(15) 1.2189(9) 0.1342(2) 0.0382(11) Uani 1 1 d . . . . .
C7 C 0.40390(16) 1.1127(9) 0.0692(2) 0.0426(11) Uani 1 1 d . . . . .
H7 H 0.407933 0.920063 0.071198 0.051 Uiso 1 1 calc R U . . .
C8 C 0.45970(15) 1.2435(10) 0.0480(2) 0.0434(12) Uani 1 1 d . . . . .
H8A H 0.476449 1.340122 0.084149 0.052 Uiso 1 1 calc R U . . .
H8B H 0.485966 1.112457 0.032175 0.052 Uiso 1 1 calc R U . . .
C9 C 0.44200(17) 1.4281(9) -0.0064(2) 0.0382(11) Uani 1 1 d . . . . .
C10 C 0.47667(17) 1.6243(10) -0.0374(2) 0.0394(12) Uani 1 1 d . . . . .
C11 C 0.53272(18) 1.6479(10) -0.0207(2) 0.0520(14) Uani 1 1 d . . . . .
H11 H 0.548263 1.530814 0.009376 0.062 Uiso 1 1 calc R U . . .
C12 C 0.5654(2) 1.8421(12) -0.0481(3) 0.0614(15) Uani 1 1 d . . . . .
H12 H 0.602626 1.856298 -0.035828 0.074 Uiso 1 1 calc R U . . .
C13 C 0.5441(2) 2.0132(11) -0.0929(3) 0.0666(16) Uani 1 1 d . . . . .
H13 H 0.566335 2.145474 -0.110666 0.080 Uiso 1 1 calc R U . . .
C14 C 0.4884(2) 1.9892(11) -0.1120(2) 0.0617(14) Uani 1 1 d . . . . .
H14 H 0.473698 2.103586 -0.143322 0.074 Uiso 1 1 calc R U . . .
C15 C 0.45507(18) 1.7958(10) -0.0845(2) 0.0495(13) Uani 1 1 d . . . . .
H15 H 0.418066 1.779957 -0.097510 0.059 Uiso 1 1 calc R U . . .
C16 C 0.31636(16) 1.0982(9) -0.0023(2) 0.0358(10) Uani 1 1 d . . . . .
C17 C 0.22861(16) 1.0232(8) -0.0553(2) 0.0431(12) Uani 1 1 d . . . . .
H17 H 0.196373 1.015017 -0.080595 0.052 Uiso 1 1 calc R U . . .
C18 C 0.23803(15) 0.8752(9) -0.0019(2) 0.0353(11) Uani 1 1 d . . . . .
C19 C 0.19679(18) 0.6745(9) 0.0210(2) 0.0411(12) Uani 1 1 d . . . . .
C20 C 0.20006(19) 0.2430(11) 0.1566(2) 0.0540(14) Uani 1 1 d . . . . .
H20 H 0.234318 0.301567 0.172272 0.065 Uiso 1 1 calc R U . . .
C21 C 0.17196(18) 0.0353(9) 0.1926(2) 0.0454(12) Uani 1 1 d . . . . .
C22 C 0.11985(19) -0.0606(10) 0.1741(2) 0.0467(13) Uani 1 1 d . . . . .
C23 C 0.09424(19) -0.2590(10) 0.2111(2) 0.0486(12) Uani 1 1 d . . . . .
C24 C 0.1209(2) -0.3631(10) 0.2652(2) 0.0556(13) Uani 1 1 d . . . . .
H24 H 0.104250 -0.498445 0.289075 0.067 Uiso 1 1 calc R U . . .
C25 C 0.1726(2) -0.2659(12) 0.2840(2) 0.0670(16) Uani 1 1 d . . . . .
H25 H 0.190252 -0.334667 0.320942 0.080 Uiso 1 1 calc R U . . .
C26 C 0.19782(19) -0.0700(11) 0.2486(2) 0.0599(14) Uani 1 1 d . . . . .
H26 H 0.232386 -0.005826 0.261784 0.072 Uiso 1 1 calc R U . . .
C27 C 0.0150(2) -0.5414(12) 0.2252(3) 0.0785(19) Uani 1 1 d . . . . .
H27A H 0.037856 -0.696949 0.225991 0.118 Uiso 1 1 calc R U . . .
H27B H -0.019977 -0.581616 0.204486 0.118 Uiso 1 1 calc R U . . .
H27C H 0.008372 -0.482301 0.269326 0.118 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 C3 1.750(5) . ?
S1 C17 1.716(4) . ?
S1 C16 1.737(4) . ?
O1 C19 1.204(5) . ?
O2 C22 1.366(5) . ?
O2 H2A 0.8200 . ?
O3 C23 1.374(5) . ?
O3 C27 1.431(6) . ?
N1 C9 1.302(5) . ?
N1 N2 1.391(5) . ?
N2 C16 1.356(5) . ?
N2 C7 1.480(5) . ?
N3 C16 1.315(5) . ?
N3 C18 1.393(5) . ?
N4 C19 1.357(5) . ?
N4 N5 1.394(5) . ?
N4 H4A 0.8600 . ?
N5 C20 1.272(5) . ?
C1 C6 1.381(6) . ?
C1 C2 1.389(7) . ?
C1 H1 0.9300 . ?
C2 C3 1.353(7) . ?
C2 H2 0.9300 . ?
C3 C4 1.376(6) . ?
C4 C5 1.382(6) . ?
C4 H4 0.9300 . ?
C5 C6 1.376(5) . ?
C5 H5 0.9300 . ?
C6 C7 1.513(6) . ?
C7 C8 1.554(5) . ?
C7 H7 0.9800 . ?
C8 C9 1.510(6) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 C10 1.440(6) . ?
C10 C11 1.392(5) . ?
C10 C15 1.393(6) . ?
C11 C12 1.375(7) . ?
C11 H11 0.9300 . ?
C12 C13 1.357(7) . ?
C12 H12 0.9300 . ?
C13 C14 1.397(6) . ?
C13 H13 0.9300 . ?
C14 C15 1.382(6) . ?
C14 H14 0.9300 . ?
C15 H15 0.9300 . ?
C17 C18 1.340(5) . ?
C17 H17 0.9300 . ?
C18 C19 1.492(6) . ?
C20 C21 1.447(6) . ?
C20 H20 0.9300 . ?
C21 C22 1.393(6) . ?
C21 C26 1.404(6) . ?
C22 C23 1.397(6) . ?
C23 C24 1.377(6) . ?
C24 C25 1.389(6) . ?
C24 H24 0.9300 . ?
C25 C26 1.366(6) . ?
C25 H25 0.9300 . ?
C26 H26 0.9300 . ?
C27 H27A 0.9600 . ?
C27 H27B 0.9600 . ?
C27 H27C 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
C17 S1 C16 87.9(2) . . ?
C22 O2 H2A 109.5 . . ?
C23 O3 C27 117.3(4) . . ?
C9 N1 N2 108.7(3) . . ?
C16 N2 N1 118.2(3) . . ?
C16 N2 C7 128.7(4) . . ?
N1 N2 C7 113.0(3) . . ?
C16 N3 C18 108.1(3) . . ?
C19 N4 N5 121.5(4) . . ?
C19 N4 H4A 119.2 . . ?
N5 N4 H4A 119.2 . . ?
C20 N5 N4 116.5(4) . . ?
C6 C1 C2 120.9(4) . . ?
C6 C1 H1 119.5 . . ?
C2 C1 H1 119.5 . . ?
C3 C2 C1 119.5(5) . . ?
C3 C2 H2 120.3 . . ?
C1 C2 H2 120.3 . . ?
C2 C3 C4 120.7(5) . . ?
C2 C3 Cl1 119.6(4) . . ?
C4 C3 Cl1 119.7(4) . . ?
C3 C4 C5 119.7(4) . . ?
C3 C4 H4 120.2 . . ?
C5 C4 H4 120.2 . . ?
C6 C5 C4 120.6(4) . . ?
C6 C5 H5 119.7 . . ?
C4 C5 H5 119.7 . . ?
C5 C6 C1 118.6(4) . . ?
C5 C6 C7 122.0(4) . . ?
C1 C6 C7 119.3(4) . . ?
N2 C7 C6 112.6(3) . . ?
N2 C7 C8 100.4(3) . . ?
C6 C7 C8 112.1(4) . . ?
N2 C7 H7 110.5 . . ?
C6 C7 H7 110.5 . . ?
C8 C7 H7 110.5 . . ?
C9 C8 C7 103.0(3) . . ?
C9 C8 H8A 111.2 . . ?
C7 C8 H8A 111.2 . . ?
C9 C8 H8B 111.2 . . ?
C7 C8 H8B 111.2 . . ?
H8A C8 H8B 109.1 . . ?
N1 C9 C10 121.5(4) . . ?
N1 C9 C8 112.6(4) . . ?
C10 C9 C8 125.8(4) . . ?
C11 C10 C15 118.3(4) . . ?
C11 C10 C9 120.7(4) . . ?
C15 C10 C9 121.1(4) . . ?
C12 C11 C10 120.9(5) . . ?
C12 C11 H11 119.6 . . ?
C10 C11 H11 119.6 . . ?
C13 C12 C11 120.8(5) . . ?
C13 C12 H12 119.6 . . ?
C11 C12 H12 119.6 . . ?
C12 C13 C14 119.5(5) . . ?
C12 C13 H13 120.2 . . ?
C14 C13 H13 120.2 . . ?
C15 C14 C13 120.1(5) . . ?
C15 C14 H14 120.0 . . ?
C13 C14 H14 120.0 . . ?
C14 C15 C10 120.3(4) . . ?
C14 C15 H15 119.8 . . ?
C10 C15 H15 119.8 . . ?
N3 C16 N2 125.5(4) . . ?
N3 C16 S1 116.4(3) . . ?
N2 C16 S1 118.1(3) . . ?
C18 C17 S1 111.3(3) . . ?
C18 C17 H17 124.4 . . ?
S1 C17 H17 124.4 . . ?
C17 C18 N3 116.4(4) . . ?
C17 C18 C19 121.4(4) . . ?
N3 C18 C19 122.2(4) . . ?
O1 C19 N4 123.9(4) . . ?
O1 C19 C18 123.3(4) . . ?
N4 C19 C18 112.8(4) . . ?
N5 C20 C21 124.0(4) . . ?
N5 C20 H20 118.0 . . ?
C21 C20 H20 118.0 . . ?
C22 C21 C26 118.9(4) . . ?
C22 C21 C20 122.3(4) . . ?
C26 C21 C20 118.7(4) . . ?
O2 C22 C21 122.7(4) . . ?
O2 C22 C23 117.3(4) . . ?
C21 C22 C23 120.0(4) . . ?
O3 C23 C24 124.7(5) . . ?
O3 C23 C22 115.3(4) . . ?
C24 C23 C22 120.1(4) . . ?
C23 C24 C25 120.0(5) . . ?
C23 C24 H24 120.0 . . ?
C25 C24 H24 120.0 . . ?
C26 C25 C24 120.4(5) . . ?
C26 C25 H25 119.8 . . ?
C24 C25 H25 119.8 . . ?
C25 C26 C21 120.6(5) . . ?
C25 C26 H26 119.7 . . ?
C21 C26 H26 119.7 . . ?
O3 C27 H27A 109.5 . . ?
O3 C27 H27B 109.5 . . ?
H27A C27 H27B 109.5 . . ?
O3 C27 H27C 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 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
C9 N1 N2 C16 -173.8(4) . . . . ?
C9 N1 N2 C7 8.1(5) . . . . ?
C19 N4 N5 C20 179.2(4) . . . . ?
C6 C1 C2 C3 -1.5(8) . . . . ?
C1 C2 C3 C4 0.0(8) . . . . ?
C1 C2 C3 Cl1 -179.0(4) . . . . ?
C2 C3 C4 C5 0.6(7) . . . . ?
Cl1 C3 C4 C5 179.6(4) . . . . ?
C3 C4 C5 C6 0.4(7) . . . . ?
C4 C5 C6 C1 -1.8(7) . . . . ?
C4 C5 C6 C7 -177.3(4) . . . . ?
C2 C1 C6 C5 2.4(7) . . . . ?
C2 C1 C6 C7 178.0(5) . . . . ?
C16 N2 C7 C6 -72.7(5) . . . . ?
N1 N2 C7 C6 105.2(4) . . . . ?
C16 N2 C7 C8 167.9(4) . . . . ?
N1 N2 C7 C8 -14.2(5) . . . . ?
C5 C6 C7 N2 -25.5(6) . . . . ?
C1 C6 C7 N2 159.0(4) . . . . ?
C5 C6 C7 C8 86.8(5) . . . . ?
C1 C6 C7 C8 -88.6(5) . . . . ?
N2 C7 C8 C9 14.0(4) . . . . ?
C6 C7 C8 C9 -105.7(4) . . . . ?
N2 N1 C9 C10 -179.7(4) . . . . ?
N2 N1 C9 C8 2.5(5) . . . . ?
C7 C8 C9 N1 -11.1(5) . . . . ?
C7 C8 C9 C10 171.1(4) . . . . ?
N1 C9 C10 C11 -173.8(4) . . . . ?
C8 C9 C10 C11 3.7(7) . . . . ?
N1 C9 C10 C15 6.5(7) . . . . ?
C8 C9 C10 C15 -176.0(4) . . . . ?
C15 C10 C11 C12 2.5(7) . . . . ?
C9 C10 C11 C12 -177.2(4) . . . . ?
C10 C11 C12 C13 -1.0(7) . . . . ?
C11 C12 C13 C14 -0.9(7) . . . . ?
C12 C13 C14 C15 1.3(7) . . . . ?
C13 C14 C15 C10 0.3(7) . . . . ?
C11 C10 C15 C14 -2.1(7) . . . . ?
C9 C10 C15 C14 177.6(4) . . . . ?
C18 N3 C16 N2 -179.2(4) . . . . ?
C18 N3 C16 S1 0.7(5) . . . . ?
N1 N2 C16 N3 -178.6(4) . . . . ?
C7 N2 C16 N3 -0.8(7) . . . . ?
N1 N2 C16 S1 1.6(5) . . . . ?
C7 N2 C16 S1 179.3(3) . . . . ?
C17 S1 C16 N3 -0.4(4) . . . . ?
C17 S1 C16 N2 179.5(4) . . . . ?
C16 S1 C17 C18 -0.1(3) . . . . ?
S1 C17 C18 N3 0.6(5) . . . . ?
S1 C17 C18 C19 -178.4(3) . . . . ?
C16 N3 C18 C17 -0.8(5) . . . . ?
C16 N3 C18 C19 178.2(4) . . . . ?
N5 N4 C19 O1 0.9(7) . . . . ?
N5 N4 C19 C18 -178.6(4) . . . . ?
C17 C18 C19 O1 1.9(7) . . . . ?
N3 C18 C19 O1 -177.0(4) . . . . ?
C17 C18 C19 N4 -178.6(4) . . . . ?
N3 C18 C19 N4 2.5(6) . . . . ?
N4 N5 C20 C21 179.6(4) . . . . ?
N5 C20 C21 C22 -1.8(8) . . . . ?
N5 C20 C21 C26 179.2(5) . . . . ?
C26 C21 C22 O2 179.4(5) . . . . ?
C20 C21 C22 O2 0.4(7) . . . . ?
C26 C21 C22 C23 -0.2(7) . . . . ?
C20 C21 C22 C23 -179.2(4) . . . . ?
C27 O3 C23 C24 0.2(7) . . . . ?
C27 O3 C23 C22 179.7(4) . . . . ?
O2 C22 C23 O3 -0.2(6) . . . . ?
C21 C22 C23 O3 179.4(4) . . . . ?
O2 C22 C23 C24 179.3(4) . . . . ?
C21 C22 C23 C24 -1.1(7) . . . . ?
O3 C23 C24 C25 -178.8(5) . . . . ?
C22 C23 C24 C25 1.7(7) . . . . ?
C23 C24 C25 C26 -1.0(8) . . . . ?
C24 C25 C26 C21 -0.3(8) . . . . ?
C22 C21 C26 C25 0.9(7) . . . . ?
C20 C21 C26 C25 179.9(5) . . . . ?

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
O2 H2A N5 0.82 1.98 2.695(5) 144.7 . yes

_refine_diff_density_max         0.225
_refine_diff_density_min         -0.271
_refine_diff_density_rms         0.040


####################################################################### 
# 
# 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_NST1
_database_code_depnum_ccdc_archive 'CCDC 1981404'
loop_
_audit_author_name
_audit_author_address
'Muhammad Ashfaq'
;University of Sargodha
Pakistan
;
_audit_update_record             
;
2021-02-05 deposited with the CCDC.	2021-03-09 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_absolute_configuration .
_chemical_name_systematic        
1-{2-[3-(4-Bromophenyl)-5-(4-methoxyphenyl)-4,5-dihydro-1H-pyrazol-1-yl]-4-methyl-1,3-thiazol-5-yl}ethan-1-one
_chemical_formula_moiety         'C22 H20 Br N3 O2 S'
_chemical_formula_sum            'C22 H20 Br N3 O2 S'
_chemical_formula_iupac          'C22 H20 Br N3 O2 S'
_chemical_formula_weight         470.38

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'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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'

_cell_length_a                   7.3329(4)
_cell_length_b                   11.3359(7)
_cell_length_c                   13.3196(7)
_cell_angle_alpha                105.658(3)
_cell_angle_beta                 92.689(2)
_cell_angle_gamma                97.255(3)
_cell_volume                     1053.76(10)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    2568
_cell_measurement_theta_min      2.788
_cell_measurement_theta_max      26.000
_cell_measurement_temperature    296(2)
_exptl_crystal_description       needle
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.18
_exptl_crystal_density_diffrn    1.482
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             480
_exptl_absorpt_coefficient_mu    2.073
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2005)'
_exptl_absorpt_correction_T_min  0.485
_exptl_absorpt_correction_T_max  0.720
_exptl_special_details           
;
;


_diffrn_ambient_temperature      296(2)
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker Kappa APEXII CCD'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 0.81
_diffrn_reflns_number            15423
_diffrn_reflns_av_unetI/netI     0.0449
_diffrn_reflns_av_R_equivalents  0.0367
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.788
_diffrn_reflns_theta_max         26.000
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measured_fraction_theta_full 0.986
_diffrn_reflns_Laue_measured_fraction_max 0.983
_diffrn_reflns_Laue_measured_fraction_full 0.986
_diffrn_reflns_point_group_measured_fraction_max 0.983
_diffrn_reflns_point_group_measured_fraction_full 0.986
_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             4064
_reflns_number_gt                2568
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0809
_refine_ls_R_factor_gt           0.0396
_refine_ls_wR_factor_ref         0.0982
_refine_ls_wR_factor_gt          0.0840
_refine_ls_goodness_of_fit_ref   1.019
_refine_ls_restrained_S_all      1.019
_refine_ls_number_reflns         4064
_refine_ls_number_parameters     265
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment    constr
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0375P)²+0.4312P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_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-2018/3  (Sheldrick, 2015)'
_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
Br1 Br 0.43855(5) 0.76803(4) -0.58665(3) 0.08699(19) Uani 1 1 d . . . . .
S1 S 0.22293(10) 1.12235(7) 0.11565(6) 0.0507(2) Uani 1 1 d . . . . .
O1 O 0.7669(3) 0.5954(2) 0.2454(2) 0.0782(7) Uani 1 1 d . . . . .
O2 O 0.1947(4) 1.3632(2) 0.2510(2) 0.0846(7) Uani 1 1 d . . . . .
N1 N 0.2679(3) 0.9059(2) -0.06403(18) 0.0479(6) Uani 1 1 d . . . . .
N2 N 0.2244(4) 0.8787(2) 0.02815(18) 0.0565(7) Uani 1 1 d . . . . .
N3 N 0.1624(3) 0.9430(2) 0.20239(18) 0.0512(6) Uani 1 1 d . . . . .
C1 C 0.3072(4) 0.7961(3) -0.2418(2) 0.0455(7) Uani 1 1 d . . . . .
C2 C 0.3227(4) 0.6825(3) -0.3122(2) 0.0559(8) Uani 1 1 d . . . . .
H2 H 0.305793 0.610736 -0.290620 0.067 Uiso 1 1 calc R U . . .
C3 C 0.3628(4) 0.6757(3) -0.4137(2) 0.0598(9) Uani 1 1 d . . . . .
H3 H 0.372895 0.599557 -0.460144 0.072 Uiso 1 1 calc R U . . .
C4 C 0.3877(4) 0.7808(3) -0.4458(2) 0.0561(8) Uani 1 1 d . . . . .
C5 C 0.3741(4) 0.8943(3) -0.3776(2) 0.0589(8) Uani 1 1 d . . . . .
H5 H 0.391681 0.965758 -0.399739 0.071 Uiso 1 1 calc R U . . .
C6 C 0.3343(4) 0.9009(3) -0.2771(2) 0.0538(8) Uani 1 1 d . . . . .
H6 H 0.325282 0.977635 -0.231303 0.065 Uiso 1 1 calc R U . . .
C7 C 0.2639(4) 0.8018(3) -0.1352(2) 0.0474(7) Uani 1 1 d . . . . .
C8 C 0.2075(5) 0.6905(3) -0.0975(2) 0.0691(9) Uani 1 1 d . . . . .
H8A H 0.295392 0.632250 -0.113673 0.083 Uiso 1 1 calc R U . . .
H8B H 0.086076 0.648910 -0.128740 0.083 Uiso 1 1 calc R U . . .
C9 C 0.2064(5) 0.7453(3) 0.0212(2) 0.0569(8) Uani 1 1 d . . . . .
H9 H 0.086981 0.718372 0.044042 0.068 Uiso 1 1 calc R U . . .
C10 C 0.3603(4) 0.7112(3) 0.0827(2) 0.0482(7) Uani 1 1 d . . . . .
C11 C 0.3307(5) 0.6049(3) 0.1154(2) 0.0575(8) Uani 1 1 d . . . . .
H11 H 0.214883 0.557075 0.101261 0.069 Uiso 1 1 calc R U . . .
C12 C 0.4692(5) 0.5686(3) 0.1683(2) 0.0596(8) Uani 1 1 d . . . . .
H12 H 0.446364 0.496873 0.189619 0.071 Uiso 1 1 calc R U . . .
C13 C 0.6408(4) 0.6381(3) 0.1897(2) 0.0542(8) Uani 1 1 d . . . . .
C14 C 0.6742(4) 0.7434(3) 0.1565(2) 0.0566(8) Uani 1 1 d . . . . .
H14 H 0.790598 0.790570 0.170197 0.068 Uiso 1 1 calc R U . . .
C15 C 0.5343(5) 0.7788(3) 0.1030(2) 0.0562(8) Uani 1 1 d . . . . .
H15 H 0.558071 0.849457 0.080214 0.067 Uiso 1 1 calc R U . . .
C16 C 0.9356(5) 0.6712(4) 0.2871(3) 0.0882(12) Uani 1 1 d . . . . .
H16A H 1.000753 0.690560 0.231346 0.132 Uiso 1 1 calc R U . . .
H16B H 1.009027 0.628304 0.322910 0.132 Uiso 1 1 calc R U . . .
H16C H 0.912010 0.746396 0.335325 0.132 Uiso 1 1 calc R U . . .
C17 C 0.2013(4) 0.9692(3) 0.1145(2) 0.0468(7) Uani 1 1 d . . . . .
C18 C 0.1508(4) 1.0506(3) 0.2783(2) 0.0485(7) Uani 1 1 d . . . . .
C19 C 0.1121(5) 1.0353(3) 0.3841(2) 0.0643(9) Uani 1 1 d . . . . .
H19A H 0.194651 1.095480 0.436795 0.096 Uiso 1 1 calc R U . . .
H19B H 0.129947 0.953597 0.386321 0.096 Uiso 1 1 calc R U . . .
H19C H -0.012980 1.047167 0.396807 0.096 Uiso 1 1 calc R U . . .
C20 C 0.1776(4) 1.1568(3) 0.2480(2) 0.0477(7) Uani 1 1 d . . . . .
C21 C 0.1725(4) 1.2867(3) 0.3004(3) 0.0595(8) Uani 1 1 d . . . . .
C22 C 0.1378(5) 1.3274(3) 0.4137(3) 0.0749(10) Uani 1 1 d . . . . .
H22A H 0.125502 1.413725 0.433050 0.112 Uiso 1 1 calc R U . . .
H22B H 0.239442 1.314161 0.455455 0.112 Uiso 1 1 calc R U . . .
H22C H 0.026379 1.280236 0.425069 0.112 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
Br1 C4 1.900(3) . ?
S1 C17 1.719(3) . ?
S1 C20 1.757(3) . ?
O1 C13 1.372(4) . ?
O1 C16 1.409(4) . ?
O2 C21 1.223(4) . ?
N1 C7 1.294(3) . ?
N1 N2 1.386(3) . ?
N2 C17 1.352(3) . ?
N2 C9 1.478(4) . ?
N3 C17 1.318(3) . ?
N3 C18 1.373(4) . ?
C1 C6 1.387(4) . ?
C1 C2 1.395(4) . ?
C1 C7 1.457(4) . ?
C2 C3 1.381(4) . ?
C2 H2 0.9300 . ?
C3 C4 1.365(4) . ?
C3 H3 0.9300 . ?
C4 C5 1.379(4) . ?
C5 C6 1.367(4) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
C7 C8 1.498(4) . ?
C8 C9 1.536(4) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 C10 1.513(4) . ?
C9 H9 0.9800 . ?
C10 C15 1.377(4) . ?
C10 C11 1.383(4) . ?
C11 C12 1.376(4) . ?
C11 H11 0.9300 . ?
C12 C13 1.371(4) . ?
C12 H12 0.9300 . ?
C13 C14 1.378(4) . ?
C14 C15 1.383(4) . ?
C14 H14 0.9300 . ?
C15 H15 0.9300 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C18 C20 1.364(4) . ?
C18 C19 1.501(4) . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
C20 C21 1.456(4) . ?
C21 C22 1.498(4) . ?
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
C17 S1 C20 87.64(14) . . ?
C13 O1 C16 119.4(3) . . ?
C7 N1 N2 107.5(2) . . ?
C17 N2 N1 121.1(2) . . ?
C17 N2 C9 125.1(2) . . ?
N1 N2 C9 113.8(2) . . ?
C17 N3 C18 109.4(2) . . ?
C6 C1 C2 117.8(3) . . ?
C6 C1 C7 122.2(3) . . ?
C2 C1 C7 120.0(3) . . ?
C3 C2 C1 120.6(3) . . ?
C3 C2 H2 119.7 . . ?
C1 C2 H2 119.7 . . ?
C4 C3 C2 119.9(3) . . ?
C4 C3 H3 120.0 . . ?
C2 C3 H3 120.0 . . ?
C3 C4 C5 120.6(3) . . ?
C3 C4 Br1 118.9(2) . . ?
C5 C4 Br1 120.5(3) . . ?
C6 C5 C4 119.4(3) . . ?
C6 C5 H5 120.3 . . ?
C4 C5 H5 120.3 . . ?
C5 C6 C1 121.7(3) . . ?
C5 C6 H6 119.2 . . ?
C1 C6 H6 119.2 . . ?
N1 C7 C1 122.1(3) . . ?
N1 C7 C8 113.7(3) . . ?
C1 C7 C8 124.1(3) . . ?
C7 C8 C9 103.2(2) . . ?
C7 C8 H8A 111.1 . . ?
C9 C8 H8A 111.1 . . ?
C7 C8 H8B 111.1 . . ?
C9 C8 H8B 111.1 . . ?
H8A C8 H8B 109.1 . . ?
N2 C9 C10 113.9(2) . . ?
N2 C9 C8 100.3(2) . . ?
C10 C9 C8 112.8(3) . . ?
N2 C9 H9 109.8 . . ?
C10 C9 H9 109.8 . . ?
C8 C9 H9 109.8 . . ?
C15 C10 C11 118.0(3) . . ?
C15 C10 C9 122.3(3) . . ?
C11 C10 C9 119.7(3) . . ?
C12 C11 C10 121.3(3) . . ?
C12 C11 H11 119.3 . . ?
C10 C11 H11 119.3 . . ?
C13 C12 C11 120.1(3) . . ?
C13 C12 H12 120.0 . . ?
C11 C12 H12 120.0 . . ?
C12 C13 O1 115.2(3) . . ?
C12 C13 C14 119.6(3) . . ?
O1 C13 C14 125.2(3) . . ?
C13 C14 C15 119.8(3) . . ?
C13 C14 H14 120.1 . . ?
C15 C14 H14 120.1 . . ?
C10 C15 C14 121.2(3) . . ?
C10 C15 H15 119.4 . . ?
C14 C15 H15 119.4 . . ?
O1 C16 H16A 109.5 . . ?
O1 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
O1 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
N3 C17 N2 120.9(3) . . ?
N3 C17 S1 117.0(2) . . ?
N2 C17 S1 122.1(2) . . ?
C20 C18 N3 115.9(3) . . ?
C20 C18 C19 128.7(3) . . ?
N3 C18 C19 115.4(3) . . ?
C18 C19 H19A 109.5 . . ?
C18 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C18 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C18 C20 C21 134.0(3) . . ?
C18 C20 S1 110.0(2) . . ?
C21 C20 S1 116.0(2) . . ?
O2 C21 C20 119.6(3) . . ?
O2 C21 C22 119.7(3) . . ?
C20 C21 C22 120.8(3) . . ?
C21 C22 H22A 109.5 . . ?
C21 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C21 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
C7 N1 N2 C17 -174.0(3) . . . . ?
C7 N1 N2 C9 5.9(3) . . . . ?
C6 C1 C2 C3 -0.3(4) . . . . ?
C7 C1 C2 C3 179.7(3) . . . . ?
C1 C2 C3 C4 0.0(4) . . . . ?
C2 C3 C4 C5 0.3(4) . . . . ?
C2 C3 C4 Br1 -178.9(2) . . . . ?
C3 C4 C5 C6 -0.3(4) . . . . ?
Br1 C4 C5 C6 178.9(2) . . . . ?
C4 C5 C6 C1 -0.1(4) . . . . ?
C2 C1 C6 C5 0.4(4) . . . . ?
C7 C1 C6 C5 -179.7(3) . . . . ?
N2 N1 C7 C1 -178.7(2) . . . . ?
N2 N1 C7 C8 2.5(3) . . . . ?
C6 C1 C7 N1 -7.6(4) . . . . ?
C2 C1 C7 N1 172.3(3) . . . . ?
C6 C1 C7 C8 171.0(3) . . . . ?
C2 C1 C7 C8 -9.0(4) . . . . ?
N1 C7 C8 C9 -9.2(4) . . . . ?
C1 C7 C8 C9 172.0(3) . . . . ?
C17 N2 C9 C10 -70.4(4) . . . . ?
N1 N2 C9 C10 109.8(3) . . . . ?
C17 N2 C9 C8 168.9(3) . . . . ?
N1 N2 C9 C8 -11.0(3) . . . . ?
C7 C8 C9 N2 11.0(3) . . . . ?
C7 C8 C9 C10 -110.5(3) . . . . ?
N2 C9 C10 C15 -27.3(4) . . . . ?
C8 C9 C10 C15 86.2(3) . . . . ?
N2 C9 C10 C11 156.3(2) . . . . ?
C8 C9 C10 C11 -90.2(3) . . . . ?
C15 C10 C11 C12 1.2(4) . . . . ?
C9 C10 C11 C12 177.8(3) . . . . ?
C10 C11 C12 C13 0.0(5) . . . . ?
C11 C12 C13 O1 178.2(3) . . . . ?
C11 C12 C13 C14 -0.9(4) . . . . ?
C16 O1 C13 C12 -168.8(3) . . . . ?
C16 O1 C13 C14 10.2(5) . . . . ?
C12 C13 C14 C15 0.6(4) . . . . ?
O1 C13 C14 C15 -178.4(3) . . . . ?
C11 C10 C15 C14 -1.5(4) . . . . ?
C9 C10 C15 C14 -178.0(3) . . . . ?
C13 C14 C15 C10 0.6(4) . . . . ?
C18 N3 C17 N2 178.5(3) . . . . ?
C18 N3 C17 S1 -1.0(3) . . . . ?
N1 N2 C17 N3 -179.1(2) . . . . ?
C9 N2 C17 N3 1.1(4) . . . . ?
N1 N2 C17 S1 0.4(4) . . . . ?
C9 N2 C17 S1 -179.5(2) . . . . ?
C20 S1 C17 N3 0.6(2) . . . . ?
C20 S1 C17 N2 -178.9(3) . . . . ?
C17 N3 C18 C20 1.0(3) . . . . ?
C17 N3 C18 C19 -178.4(2) . . . . ?
N3 C18 C20 C21 177.9(3) . . . . ?
C19 C18 C20 C21 -2.8(5) . . . . ?
N3 C18 C20 S1 -0.6(3) . . . . ?
C19 C18 C20 S1 178.7(2) . . . . ?
C17 S1 C20 C18 0.0(2) . . . . ?
C17 S1 C20 C21 -178.8(2) . . . . ?
C18 C20 C21 O2 -176.7(3) . . . . ?
S1 C20 C21 O2 1.7(4) . . . . ?
C18 C20 C21 C22 2.5(5) . . . . ?
S1 C20 C21 C22 -179.1(2) . . . . ?

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
C8 H8B O2 0.97 2.53 3.400(5) 149.1 2_575 yes
C12 H12 O2 0.93 2.54 3.331(4) 142.5 1_545 yes

_refine_diff_density_max         0.425
_refine_diff_density_min         -0.439
_refine_diff_density_rms         0.046


