# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2020

####################################################################### 
# 
# 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_A15QAU
_database_code_depnum_ccdc_archive 'CCDC 1009298'
loop_
_audit_author_name
_audit_author_address
'Muhammad Nawaz Tahir'
;University of Sargodha, Pakistan
Pakistan
;
_audit_update_record             
;
2020-05-19 deposited with the CCDC.	2020-07-29 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        
3-[2-(3-Phenyl-5-(4-chlorophenyl)-4,5-dihydro-1H-pyrazol-1-yl)-1,3-thiazol-4-yl]-2H-1-benzopyran-2-one
_chemical_formula_moiety         'C27 H18 Cl N3 O2 S'
_chemical_formula_sum            'C27 H18 Cl N3 O2 S'
_chemical_formula_iupac          'C27 H18 Cl N3 O2 S'
_chemical_formula_weight         483.95

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

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

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   8.5233(9)
_cell_length_b                   22.329(3)
_cell_length_c                   12.3340(12)
_cell_angle_alpha                90
_cell_angle_beta                 106.201(4)
_cell_angle_gamma                90
_cell_volume                     2254.1(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2816
_cell_measurement_theta_min      1.824
_cell_measurement_theta_max      27.425
_cell_measurement_temperature    296(2)
_exptl_crystal_description       plate
_exptl_crystal_colour            'light yellow'
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.20
_exptl_crystal_density_diffrn    1.426
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1000
_exptl_absorpt_coefficient_mu    0.294
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2005)'
_exptl_absorpt_correction_T_min  0.675
_exptl_absorpt_correction_T_max  0.746
_shelx_estimated_absorpt_T_min   0.904
_shelx_estimated_absorpt_T_max   0.944
_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            19198
_diffrn_reflns_av_unetI/netI     0.0678
_diffrn_reflns_av_R_equivalents  0.0512
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_k_max       28
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         1.824
_diffrn_reflns_theta_max         27.425
_diffrn_reflns_theta_full        27.425
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measured_fraction_theta_full 0.990
_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             5071
_reflns_number_gt                2816
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.1126
_refine_ls_R_factor_gt           0.0514
_refine_ls_wR_factor_ref         0.1274
_refine_ls_wR_factor_gt          0.1055
_refine_ls_goodness_of_fit_ref   1.000
_refine_ls_restrained_S_all      1.000
_refine_ls_number_reflns         5071
_refine_ls_number_parameters     307
_refine_ls_number_restraints     0
_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)+(0.0545P)²+0.0764P] 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
Cl1 Cl 0.04221(9) 0.29620(4) 0.58868(6) 0.0736(3) Uani 1 1 d . . . . .
S1 S 0.17245(8) -0.00855(3) 0.95082(5) 0.0480(2) Uani 1 1 d . . . . .
O1 O -0.0585(2) -0.11425(8) 0.62919(14) 0.0559(5) Uani 1 1 d . . . . .
O2 O 0.01177(19) -0.10589(7) 0.47189(12) 0.0429(4) Uani 1 1 d . . . . .
N1 N 0.2852(2) 0.02305(8) 0.78524(14) 0.0356(5) Uani 1 1 d . . . . .
N2 N 0.3906(3) 0.07795(9) 0.95103(15) 0.0487(5) Uani 1 1 d . . . . .
N3 N 0.3974(2) 0.08579(9) 1.06378(15) 0.0444(5) Uani 1 1 d . . . . .
C1 C 0.1040(3) -0.08194(10) 0.40713(18) 0.0371(6) Uani 1 1 d . . . . .
C2 C 0.0789(3) -0.10410(11) 0.2991(2) 0.0475(6) Uani 1 1 d . . . . .
H2 H 0.003250 -0.134406 0.272031 0.057 Uiso 1 1 calc R U . . .
C3 C 0.1683(3) -0.08030(12) 0.2327(2) 0.0533(7) Uani 1 1 d . . . . .
H3 H 0.153029 -0.094914 0.159864 0.064 Uiso 1 1 calc R U . . .
C4 C 0.2808(3) -0.03502(12) 0.2717(2) 0.0507(7) Uani 1 1 d . . . . .
H4 H 0.339350 -0.019146 0.225166 0.061 Uiso 1 1 calc R U . . .
C5 C 0.3054(3) -0.01365(11) 0.37969(19) 0.0434(6) Uani 1 1 d . . . . .
H5 H 0.381709 0.016509 0.406212 0.052 Uiso 1 1 calc R U . . .
C6 C 0.2164(3) -0.03688(10) 0.45033(18) 0.0342(5) Uani 1 1 d . . . . .
C7 C 0.2353(3) -0.01760(10) 0.56404(17) 0.0348(5) Uani 1 1 d . . . . .
H7 H 0.309175 0.012870 0.593832 0.042 Uiso 1 1 calc R U . . .
C8 C 0.1494(3) -0.04230(10) 0.62900(17) 0.0318(5) Uani 1 1 d . . . . .
C9 C 0.0294(3) -0.08891(11) 0.58231(19) 0.0392(6) Uani 1 1 d . . . . .
C10 C 0.1736(3) -0.02294(10) 0.74657(18) 0.0341(5) Uani 1 1 d . . . . .
C11 C 0.1024(3) -0.04512(11) 0.82301(18) 0.0432(6) Uani 1 1 d . . . . .
H11 H 0.026024 -0.075948 0.808794 0.052 Uiso 1 1 calc R U . . .
C12 C 0.2946(3) 0.03454(10) 0.88997(18) 0.0378(6) Uani 1 1 d . . . . .
C13 C 0.4829(3) 0.12331(11) 0.90696(19) 0.0433(6) Uani 1 1 d . . . . .
H13 H 0.556725 0.103711 0.869669 0.052 Uiso 1 1 calc R U . . .
C14 C 0.3706(3) 0.16601(10) 0.82631(18) 0.0383(6) Uani 1 1 d . . . . .
C15 C 0.3646(3) 0.16741(12) 0.7131(2) 0.0496(7) Uani 1 1 d . . . . .
H15 H 0.430187 0.141416 0.686130 0.060 Uiso 1 1 calc R U . . .
C16 C 0.2629(3) 0.20668(12) 0.6396(2) 0.0525(7) Uani 1 1 d . . . . .
H16 H 0.258743 0.206734 0.563403 0.063 Uiso 1 1 calc R U . . .
C17 C 0.1684(3) 0.24553(11) 0.6798(2) 0.0451(6) Uani 1 1 d . . . . .
C18 C 0.1705(3) 0.24489(12) 0.7920(2) 0.0515(7) Uani 1 1 d . . . . .
H18 H 0.105331 0.271151 0.818809 0.062 Uiso 1 1 calc R U . . .
C19 C 0.2708(3) 0.20469(12) 0.8635(2) 0.0492(7) Uani 1 1 d . . . . .
H19 H 0.271177 0.203607 0.938925 0.059 Uiso 1 1 calc R U . . .
C20 C 0.5812(3) 0.15208(12) 1.01820(19) 0.0507(7) Uani 1 1 d . . . . .
H20A H 0.695411 0.140605 1.036510 0.061 Uiso 1 1 calc R U . . .
H20B H 0.573344 0.195407 1.014252 0.061 Uiso 1 1 calc R U . . .
C21 C 0.5016(3) 0.12753(11) 1.10358(19) 0.0429(6) Uani 1 1 d . . . . .
C22 C 0.5352(3) 0.14705(11) 1.22090(19) 0.0452(6) Uani 1 1 d . . . . .
C23 C 0.4379(3) 0.12866(12) 1.2885(2) 0.0548(7) Uani 1 1 d . . . . .
H23 H 0.347323 0.104643 1.257554 0.066 Uiso 1 1 calc R U . . .
C24 C 0.4729(4) 0.14528(13) 1.4000(2) 0.0667(9) Uani 1 1 d . . . . .
H24 H 0.406825 0.132554 1.444072 0.080 Uiso 1 1 calc R U . . .
C25 C 0.6068(4) 0.18093(14) 1.4458(3) 0.0738(10) Uani 1 1 d . . . . .
H25 H 0.631397 0.191946 1.521425 0.089 Uiso 1 1 calc R U . . .
C26 C 0.7037(4) 0.20030(14) 1.3816(3) 0.0748(10) Uani 1 1 d . . . . .
H26 H 0.793482 0.224509 1.413591 0.090 Uiso 1 1 calc R U . . .
C27 C 0.6685(3) 0.18388(12) 1.2676(2) 0.0628(8) Uani 1 1 d . . . . .
H27 H 0.733812 0.197507 1.223621 0.075 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 C17 1.740(3) . ?
S1 C11 1.727(2) . ?
S1 C12 1.735(2) . ?
O1 C9 1.207(3) . ?
O2 C1 1.375(3) . ?
O2 C9 1.381(3) . ?
N1 C12 1.297(3) . ?
N1 C10 1.391(3) . ?
N2 C12 1.353(3) . ?
N2 N3 1.387(2) . ?
N2 C13 1.476(3) . ?
N3 C21 1.287(3) . ?
C1 C2 1.381(3) . ?
C1 C6 1.389(3) . ?
C2 C3 1.372(3) . ?
C2 H2 0.9300 . ?
C3 C4 1.384(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.374(3) . ?
C4 H4 0.9300 . ?
C5 C6 1.404(3) . ?
C5 H5 0.9300 . ?
C6 C7 1.433(3) . ?
C7 C8 1.346(3) . ?
C7 H7 0.9300 . ?
C8 C9 1.460(3) . ?
C8 C10 1.472(3) . ?
C10 C11 1.350(3) . ?
C11 H11 0.9300 . ?
C13 C14 1.511(3) . ?
C13 C20 1.535(3) . ?
C13 H13 0.9800 . ?
C14 C19 1.377(3) . ?
C14 C15 1.383(3) . ?
C15 C16 1.380(3) . ?
C15 H15 0.9300 . ?
C16 C17 1.368(3) . ?
C16 H16 0.9300 . ?
C17 C18 1.378(3) . ?
C18 C19 1.376(3) . ?
C18 H18 0.9300 . ?
C19 H19 0.9300 . ?
C20 C21 1.507(3) . ?
C20 H20A 0.9700 . ?
C20 H20B 0.9700 . ?
C21 C22 1.461(3) . ?
C22 C27 1.391(3) . ?
C22 C23 1.392(3) . ?
C23 C24 1.375(3) . ?
C23 H23 0.9300 . ?
C24 C25 1.376(4) . ?
C24 H24 0.9300 . ?
C25 C26 1.365(4) . ?
C25 H25 0.9300 . ?
C26 C27 1.402(4) . ?
C26 H26 0.9300 . ?
C27 H27 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
C11 S1 C12 87.91(11) . . ?
C1 O2 C9 122.90(18) . . ?
C12 N1 C10 109.49(19) . . ?
C12 N2 N3 119.87(19) . . ?
C12 N2 C13 126.01(18) . . ?
N3 N2 C13 113.91(18) . . ?
C21 N3 N2 107.77(19) . . ?
O2 C1 C2 117.5(2) . . ?
O2 C1 C6 120.25(19) . . ?
C2 C1 C6 122.3(2) . . ?
C3 C2 C1 118.4(2) . . ?
C3 C2 H2 120.8 . . ?
C1 C2 H2 120.8 . . ?
C2 C3 C4 121.4(2) . . ?
C2 C3 H3 119.3 . . ?
C4 C3 H3 119.3 . . ?
C5 C4 C3 119.6(2) . . ?
C5 C4 H4 120.2 . . ?
C3 C4 H4 120.2 . . ?
C4 C5 C6 120.7(2) . . ?
C4 C5 H5 119.7 . . ?
C6 C5 H5 119.7 . . ?
C1 C6 C5 117.6(2) . . ?
C1 C6 C7 118.0(2) . . ?
C5 C6 C7 124.3(2) . . ?
C8 C7 C6 121.9(2) . . ?
C8 C7 H7 119.0 . . ?
C6 C7 H7 119.0 . . ?
C7 C8 C9 119.7(2) . . ?
C7 C8 C10 121.1(2) . . ?
C9 C8 C10 119.24(19) . . ?
O1 C9 O2 115.6(2) . . ?
O1 C9 C8 127.2(2) . . ?
O2 C9 C8 117.2(2) . . ?
C11 C10 N1 115.4(2) . . ?
C11 C10 C8 127.9(2) . . ?
N1 C10 C8 116.70(19) . . ?
C10 C11 S1 110.85(18) . . ?
C10 C11 H11 124.6 . . ?
S1 C11 H11 124.6 . . ?
N1 C12 N2 123.7(2) . . ?
N1 C12 S1 116.32(17) . . ?
N2 C12 S1 119.93(17) . . ?
N2 C13 C14 111.73(19) . . ?
N2 C13 C20 99.92(17) . . ?
C14 C13 C20 114.3(2) . . ?
N2 C13 H13 110.2 . . ?
C14 C13 H13 110.2 . . ?
C20 C13 H13 110.2 . . ?
C19 C14 C15 118.0(2) . . ?
C19 C14 C13 120.9(2) . . ?
C15 C14 C13 121.1(2) . . ?
C16 C15 C14 121.2(2) . . ?
C16 C15 H15 119.4 . . ?
C14 C15 H15 119.4 . . ?
C17 C16 C15 119.3(2) . . ?
C17 C16 H16 120.4 . . ?
C15 C16 H16 120.4 . . ?
C16 C17 C18 120.9(2) . . ?
C16 C17 Cl1 119.89(19) . . ?
C18 C17 Cl1 119.2(2) . . ?
C19 C18 C17 118.8(2) . . ?
C19 C18 H18 120.6 . . ?
C17 C18 H18 120.6 . . ?
C18 C19 C14 121.8(2) . . ?
C18 C19 H19 119.1 . . ?
C14 C19 H19 119.1 . . ?
C21 C20 C13 103.4(2) . . ?
C21 C20 H20A 111.1 . . ?
C13 C20 H20A 111.1 . . ?
C21 C20 H20B 111.1 . . ?
C13 C20 H20B 111.1 . . ?
H20A C20 H20B 109.0 . . ?
N3 C21 C22 121.2(2) . . ?
N3 C21 C20 113.3(2) . . ?
C22 C21 C20 125.6(2) . . ?
C27 C22 C23 118.7(2) . . ?
C27 C22 C21 119.9(3) . . ?
C23 C22 C21 121.3(2) . . ?
C24 C23 C22 121.3(3) . . ?
C24 C23 H23 119.3 . . ?
C22 C23 H23 119.3 . . ?
C23 C24 C25 119.4(3) . . ?
C23 C24 H24 120.3 . . ?
C25 C24 H24 120.3 . . ?
C26 C25 C24 120.8(3) . . ?
C26 C25 H25 119.6 . . ?
C24 C25 H25 119.6 . . ?
C25 C26 C27 120.3(3) . . ?
C25 C26 H26 119.9 . . ?
C27 C26 H26 119.9 . . ?
C22 C27 C26 119.4(3) . . ?
C22 C27 H27 120.3 . . ?
C26 C27 H27 120.3 . . ?

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
C12 N2 N3 C21 177.1(2) . . . . ?
C13 N2 N3 C21 -7.8(3) . . . . ?
C9 O2 C1 C2 177.8(2) . . . . ?
C9 O2 C1 C6 -2.7(3) . . . . ?
O2 C1 C2 C3 179.2(2) . . . . ?
C6 C1 C2 C3 -0.3(4) . . . . ?
C1 C2 C3 C4 -0.3(4) . . . . ?
C2 C3 C4 C5 0.7(4) . . . . ?
C3 C4 C5 C6 -0.6(4) . . . . ?
O2 C1 C6 C5 -179.1(2) . . . . ?
C2 C1 C6 C5 0.3(3) . . . . ?
O2 C1 C6 C7 1.5(3) . . . . ?
C2 C1 C6 C7 -179.0(2) . . . . ?
C4 C5 C6 C1 0.1(3) . . . . ?
C4 C5 C6 C7 179.4(2) . . . . ?
C1 C6 C7 C8 0.8(3) . . . . ?
C5 C6 C7 C8 -178.5(2) . . . . ?
C6 C7 C8 C9 -1.8(3) . . . . ?
C6 C7 C8 C10 178.41(19) . . . . ?
C1 O2 C9 O1 -179.2(2) . . . . ?
C1 O2 C9 C8 1.6(3) . . . . ?
C7 C8 C9 O1 -178.5(2) . . . . ?
C10 C8 C9 O1 1.3(4) . . . . ?
C7 C8 C9 O2 0.7(3) . . . . ?
C10 C8 C9 O2 -179.57(19) . . . . ?
C12 N1 C10 C11 -0.3(3) . . . . ?
C12 N1 C10 C8 -179.23(19) . . . . ?
C7 C8 C10 C11 -176.8(2) . . . . ?
C9 C8 C10 C11 3.5(4) . . . . ?
C7 C8 C10 N1 1.9(3) . . . . ?
C9 C8 C10 N1 -177.83(19) . . . . ?
N1 C10 C11 S1 0.2(3) . . . . ?
C8 C10 C11 S1 178.98(18) . . . . ?
C12 S1 C11 C10 -0.06(19) . . . . ?
C10 N1 C12 N2 -178.6(2) . . . . ?
C10 N1 C12 S1 0.3(2) . . . . ?
N3 N2 C12 N1 -177.8(2) . . . . ?
C13 N2 C12 N1 7.8(4) . . . . ?
N3 N2 C12 S1 3.4(3) . . . . ?
C13 N2 C12 S1 -171.04(18) . . . . ?
C11 S1 C12 N1 -0.14(19) . . . . ?
C11 S1 C12 N2 178.8(2) . . . . ?
C12 N2 C13 C14 66.0(3) . . . . ?
N3 N2 C13 C14 -108.7(2) . . . . ?
C12 N2 C13 C20 -172.7(2) . . . . ?
N3 N2 C13 C20 12.6(3) . . . . ?
N2 C13 C14 C19 66.0(3) . . . . ?
C20 C13 C14 C19 -46.6(3) . . . . ?
N2 C13 C14 C15 -113.9(2) . . . . ?
C20 C13 C14 C15 133.5(2) . . . . ?
C19 C14 C15 C16 0.6(4) . . . . ?
C13 C14 C15 C16 -179.5(2) . . . . ?
C14 C15 C16 C17 1.0(4) . . . . ?
C15 C16 C17 C18 -1.6(4) . . . . ?
C15 C16 C17 Cl1 178.9(2) . . . . ?
C16 C17 C18 C19 0.6(4) . . . . ?
Cl1 C17 C18 C19 -179.97(19) . . . . ?
C17 C18 C19 C14 1.1(4) . . . . ?
C15 C14 C19 C18 -1.7(4) . . . . ?
C13 C14 C19 C18 178.4(2) . . . . ?
N2 C13 C20 C21 -11.9(2) . . . . ?
C14 C13 C20 C21 107.6(2) . . . . ?
N2 N3 C21 C22 179.2(2) . . . . ?
N2 N3 C21 C20 -1.2(3) . . . . ?
C13 C20 C21 N3 9.0(3) . . . . ?
C13 C20 C21 C22 -171.4(2) . . . . ?
N3 C21 C22 C27 168.1(2) . . . . ?
C20 C21 C22 C27 -11.5(4) . . . . ?
N3 C21 C22 C23 -10.8(4) . . . . ?
C20 C21 C22 C23 169.7(2) . . . . ?
C27 C22 C23 C24 -1.2(4) . . . . ?
C21 C22 C23 C24 177.7(2) . . . . ?
C22 C23 C24 C25 0.1(4) . . . . ?
C23 C24 C25 C26 0.6(4) . . . . ?
C24 C25 C26 C27 -0.3(5) . . . . ?
C23 C22 C27 C26 1.5(4) . . . . ?
C21 C22 C27 C26 -177.3(2) . . . . ?
C25 C26 C27 C22 -0.8(4) . . . . ?

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
C11 H11 O1 0.93 2.29 2.855(3) 118.2 . yes

_refine_diff_density_max         0.212
_refine_diff_density_min         -0.334
_refine_diff_density_rms         0.049

####################################################################### 
# 
# 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_A27_0m
_database_code_depnum_ccdc_archive 'CCDC 1009300'
loop_
_audit_author_name
_audit_author_address
'Muhammad Nawaz Tahir'
;University of Sargodha, Pakistan
Pakistan
;
_audit_update_record             
;
2020-05-19 deposited with the CCDC.	2020-07-29 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        
;
3-[2-(3-(4-Chlorophenyl)-5-(4-methylphenyl)-4,5-dihydro-1H-pyrazol-1-yl)-1,3
-thiazol-4-yl]-2H-1-benzopyran-2-one
;
_chemical_formula_moiety         'C28 H20 Cl N3 O2 S'
_chemical_formula_sum            'C28 H20 Cl N3 O2 S'
_chemical_formula_iupac          'C28 H20 Cl N3 O2 S'
_chemical_formula_weight         497.98

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      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                   10.2870(10)
_cell_length_b                   10.938(2)
_cell_length_c                   11.3049(10)
_cell_angle_alpha                97.749(5)
_cell_angle_beta                 100.075(4)
_cell_angle_gamma                101.222(5)
_cell_volume                     1209.6(3)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    2614
_cell_measurement_theta_min      1.858
_cell_measurement_theta_max      27.000
_cell_measurement_temperature    296(2)
_exptl_crystal_description       needle
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.37
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.21
_exptl_crystal_density_diffrn    1.367
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             516
_exptl_absorpt_coefficient_mu    0.276
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2005)'
_exptl_absorpt_correction_T_min  0.685
_exptl_absorpt_correction_T_max  0.746
_shelx_estimated_absorpt_T_min   0.905
_shelx_estimated_absorpt_T_max   0.944
_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 7.83
_diffrn_reflns_number            19681
_diffrn_reflns_av_unetI/netI     0.0618
_diffrn_reflns_av_R_equivalents  0.0421
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         1.858
_diffrn_reflns_theta_max         27.000
_diffrn_reflns_theta_full        27.000
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measured_fraction_theta_full 0.984
_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             5203
_reflns_number_gt                2614
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.1275
_refine_ls_R_factor_gt           0.0527
_refine_ls_wR_factor_ref         0.1447
_refine_ls_wR_factor_gt          0.1156
_refine_ls_goodness_of_fit_ref   1.013
_refine_ls_restrained_S_all      1.013
_refine_ls_number_reflns         5203
_refine_ls_number_parameters     317
_refine_ls_number_restraints     0
_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)+(0.0596P)²+0.0729P] 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

_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 1.00802(9) -0.44785(10) -0.21777(8) 0.1157(4) Uani 1 1 d . . . . .
S1 S 0.65898(8) 0.21458(7) 0.02936(6) 0.0678(3) Uani 1 1 d . . . . .
O1 O 0.4945(2) 0.55011(17) 0.15580(17) 0.0807(6) Uani 1 1 d . . . . .
O2 O 0.39057(19) 0.56948(16) 0.30709(16) 0.0673(5) Uani 1 1 d . . . . .
N1 N 0.5572(2) 0.18809(19) 0.22014(17) 0.0553(6) Uani 1 1 d . . . . .
N2 N 0.6672(3) 0.0292(2) 0.15966(19) 0.0756(7) Uani 1 1 d . . . . .
N3 N 0.7257(2) -0.0226(2) 0.06985(18) 0.0644(6) Uani 1 1 d . . . . .
C1 C 0.3325(3) 0.5241(3) 0.3974(2) 0.0582(7) Uani 1 1 d . . . . .
C2 C 0.2735(3) 0.6033(3) 0.4646(3) 0.0735(8) Uani 1 1 d . . . . .
H2 H 0.273850 0.684652 0.448841 0.088 Uiso 1 1 calc R U . . .
C3 C 0.2145(3) 0.5610(3) 0.5548(3) 0.0812(9) Uani 1 1 d . . . . .
H3 H 0.174038 0.613854 0.600709 0.097 Uiso 1 1 calc R U . . .
C4 C 0.2141(3) 0.4406(3) 0.5785(3) 0.0836(9) Uani 1 1 d . . . . .
H4 H 0.172834 0.412096 0.639628 0.100 Uiso 1 1 calc R U . . .
C5 C 0.2748(3) 0.3630(3) 0.5118(3) 0.0742(8) Uani 1 1 d . . . . .
H5 H 0.275237 0.282284 0.528990 0.089 Uiso 1 1 calc R U . . .
C6 C 0.3358(3) 0.4029(2) 0.4187(2) 0.0544(7) Uani 1 1 d . . . . .
C7 C 0.4041(3) 0.3309(2) 0.3464(2) 0.0568(7) Uani 1 1 d . . . . .
H7 H 0.409541 0.250319 0.361450 0.068 Uiso 1 1 calc R U . . .
C8 C 0.4610(2) 0.3740(2) 0.2573(2) 0.0492(6) Uani 1 1 d . . . . .
C9 C 0.4523(3) 0.5001(2) 0.2334(2) 0.0577(7) Uani 1 1 d . . . . .
C10 C 0.5335(2) 0.3001(2) 0.1851(2) 0.0503(6) Uani 1 1 d . . . . .
C11 C 0.5813(3) 0.3270(2) 0.0858(2) 0.0619(7) Uani 1 1 d . . . . .
H11 H 0.572951 0.398716 0.051985 0.074 Uiso 1 1 calc R U . . .
C12 C 0.6226(3) 0.1362(2) 0.1467(2) 0.0569(7) Uani 1 1 d . . . . .
C13 C 0.6341(3) -0.0542(2) 0.2462(2) 0.0617(7) Uani 1 1 d . . . . .
H13 H 0.535908 -0.075210 0.240318 0.074 Uiso 1 1 calc R U . . .
C14 C 0.7049(3) 0.0021(2) 0.3762(2) 0.0516(6) Uani 1 1 d . . . . .
C15 C 0.6476(3) -0.0334(2) 0.4698(2) 0.0646(7) Uani 1 1 d . . . . .
H15 H 0.563675 -0.089811 0.452379 0.078 Uiso 1 1 calc R U . . .
C16 C 0.7123(4) 0.0133(3) 0.5910(3) 0.0785(9) Uani 1 1 d . . . . .
H16 H 0.670587 -0.012304 0.653016 0.094 Uiso 1 1 calc R U . . .
C17 C 0.8348(4) 0.0953(3) 0.6203(3) 0.0814(9) Uani 1 1 d . . . . .
C18 C 0.8927(3) 0.1289(3) 0.5262(4) 0.0940(10) Uani 1 1 d . . . . .
H18 H 0.977511 0.183814 0.543908 0.113 Uiso 1 1 calc R U . . .
C19 C 0.8292(3) 0.0839(3) 0.4052(3) 0.0798(9) Uani 1 1 d . . . . .
H19 H 0.871357 0.109496 0.343461 0.096 Uiso 1 1 calc R U . . .
C20 C 0.9034(5) 0.1481(4) 0.7526(3) 0.1445(17) Uani 1 1 d . . . . .
H20A H 0.836688 0.142154 0.802444 0.217 Uiso 1 1 calc R U . . .
H20B H 0.948313 0.235163 0.759782 0.217 Uiso 1 1 calc R U . . .
H20C H 0.968672 0.100324 0.779041 0.217 Uiso 1 1 calc R U . . .
C21 C 0.6810(3) -0.1720(2) 0.1946(2) 0.0717(8) Uani 1 1 d . . . . .
H21A H 0.750553 -0.191245 0.254325 0.086 Uiso 1 1 calc R U . . .
H21B H 0.605680 -0.245162 0.169309 0.086 Uiso 1 1 calc R U . . .
C22 C 0.7358(3) -0.1342(3) 0.0874(2) 0.0564(7) Uani 1 1 d . . . . .
C23 C 0.8008(3) -0.2114(3) 0.0106(2) 0.0566(7) Uani 1 1 d . . . . .
C24 C 0.7947(3) -0.3366(3) 0.0203(2) 0.0656(8) Uani 1 1 d . . . . .
H24 H 0.747989 -0.372163 0.075292 0.079 Uiso 1 1 calc R U . . .
C25 C 0.8576(3) -0.4102(3) -0.0510(3) 0.0733(8) Uani 1 1 d . . . . .
H25 H 0.852123 -0.494903 -0.044720 0.088 Uiso 1 1 calc R U . . .
C26 C 0.9270(3) -0.3578(3) -0.1296(3) 0.0748(9) Uani 1 1 d . . . . .
C27 C 0.9349(3) -0.2338(4) -0.1410(3) 0.0871(10) Uani 1 1 d . . . . .
H27 H 0.983026 -0.198687 -0.195292 0.105 Uiso 1 1 calc R U . . .
C28 C 0.8710(3) -0.1616(3) -0.0715(3) 0.0753(8) Uani 1 1 d . . . . .
H28 H 0.875195 -0.077661 -0.080070 0.090 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 C26 1.733(3) . ?
S1 C11 1.705(3) . ?
S1 C12 1.729(3) . ?
O1 C9 1.195(3) . ?
O2 C9 1.369(3) . ?
O2 C1 1.371(3) . ?
N1 C12 1.297(3) . ?
N1 C10 1.390(3) . ?
N2 C12 1.354(3) . ?
N2 N3 1.380(3) . ?
N2 C13 1.463(3) . ?
N3 C22 1.284(3) . ?
C1 C2 1.373(3) . ?
C1 C6 1.385(3) . ?
C2 C3 1.362(4) . ?
C2 H2 0.9300 . ?
C3 C4 1.379(4) . ?
C3 H3 0.9300 . ?
C4 C5 1.369(4) . ?
C4 H4 0.9300 . ?
C5 C6 1.393(3) . ?
C5 H5 0.9300 . ?
C6 C7 1.423(3) . ?
C7 C8 1.344(3) . ?
C7 H7 0.9300 . ?
C8 C9 1.457(3) . ?
C8 C10 1.465(3) . ?
C10 C11 1.346(3) . ?
C11 H11 0.9300 . ?
C13 C14 1.509(3) . ?
C13 C21 1.540(3) . ?
C13 H13 0.9800 . ?
C14 C15 1.362(3) . ?
C14 C19 1.369(4) . ?
C15 C16 1.394(4) . ?
C15 H15 0.9300 . ?
C16 C17 1.355(4) . ?
C16 H16 0.9300 . ?
C17 C18 1.365(4) . ?
C17 C20 1.519(4) . ?
C18 C19 1.385(4) . ?
C18 H18 0.9300 . ?
C19 H19 0.9300 . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
C21 C22 1.497(4) . ?
C21 H21A 0.9700 . ?
C21 H21B 0.9700 . ?
C22 C23 1.463(3) . ?
C23 C28 1.377(4) . ?
C23 C24 1.379(4) . ?
C24 C25 1.388(3) . ?
C24 H24 0.9300 . ?
C25 C26 1.352(4) . ?
C25 H25 0.9300 . ?
C26 C27 1.368(4) . ?
C27 C28 1.374(4) . ?
C27 H27 0.9300 . ?
C28 H28 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
C11 S1 C12 87.49(13) . . ?
C9 O2 C1 123.3(2) . . ?
C12 N1 C10 109.4(2) . . ?
C12 N2 N3 118.6(2) . . ?
C12 N2 C13 125.9(2) . . ?
N3 N2 C13 114.1(2) . . ?
C22 N3 N2 108.1(2) . . ?
O2 C1 C2 117.5(3) . . ?
O2 C1 C6 120.0(2) . . ?
C2 C1 C6 122.5(3) . . ?
C3 C2 C1 119.0(3) . . ?
C3 C2 H2 120.5 . . ?
C1 C2 H2 120.5 . . ?
C2 C3 C4 120.6(3) . . ?
C2 C3 H3 119.7 . . ?
C4 C3 H3 119.7 . . ?
C5 C4 C3 119.9(3) . . ?
C5 C4 H4 120.1 . . ?
C3 C4 H4 120.1 . . ?
C4 C5 C6 121.2(3) . . ?
C4 C5 H5 119.4 . . ?
C6 C5 H5 119.4 . . ?
C1 C6 C5 116.9(2) . . ?
C1 C6 C7 117.6(2) . . ?
C5 C6 C7 125.5(2) . . ?
C8 C7 C6 123.0(2) . . ?
C8 C7 H7 118.5 . . ?
C6 C7 H7 118.5 . . ?
C7 C8 C9 118.6(2) . . ?
C7 C8 C10 122.6(2) . . ?
C9 C8 C10 118.8(2) . . ?
O1 C9 O2 116.1(2) . . ?
O1 C9 C8 126.5(3) . . ?
O2 C9 C8 117.4(2) . . ?
C11 C10 N1 114.3(2) . . ?
C11 C10 C8 127.8(2) . . ?
N1 C10 C8 118.0(2) . . ?
C10 C11 S1 112.3(2) . . ?
C10 C11 H11 123.9 . . ?
S1 C11 H11 123.9 . . ?
N1 C12 N2 124.1(2) . . ?
N1 C12 S1 116.5(2) . . ?
N2 C12 S1 119.3(2) . . ?
N2 C13 C14 113.0(2) . . ?
N2 C13 C21 100.81(19) . . ?
C14 C13 C21 113.4(2) . . ?
N2 C13 H13 109.8 . . ?
C14 C13 H13 109.8 . . ?
C21 C13 H13 109.8 . . ?
C15 C14 C19 117.8(3) . . ?
C15 C14 C13 119.7(2) . . ?
C19 C14 C13 122.5(2) . . ?
C14 C15 C16 121.3(3) . . ?
C14 C15 H15 119.4 . . ?
C16 C15 H15 119.4 . . ?
C17 C16 C15 121.2(3) . . ?
C17 C16 H16 119.4 . . ?
C15 C16 H16 119.4 . . ?
C16 C17 C18 117.3(3) . . ?
C16 C17 C20 121.0(4) . . ?
C18 C17 C20 121.7(4) . . ?
C17 C18 C19 122.2(3) . . ?
C17 C18 H18 118.9 . . ?
C19 C18 H18 118.9 . . ?
C14 C19 C18 120.3(3) . . ?
C14 C19 H19 119.8 . . ?
C18 C19 H19 119.8 . . ?
C17 C20 H20A 109.5 . . ?
C17 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C17 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C22 C21 C13 103.3(2) . . ?
C22 C21 H21A 111.1 . . ?
C13 C21 H21A 111.1 . . ?
C22 C21 H21B 111.1 . . ?
C13 C21 H21B 111.1 . . ?
H21A C21 H21B 109.1 . . ?
N3 C22 C23 121.3(2) . . ?
N3 C22 C21 113.6(2) . . ?
C23 C22 C21 125.0(2) . . ?
C28 C23 C24 118.2(2) . . ?
C28 C23 C22 121.5(3) . . ?
C24 C23 C22 120.3(3) . . ?
C23 C24 C25 120.7(3) . . ?
C23 C24 H24 119.6 . . ?
C25 C24 H24 119.6 . . ?
C26 C25 C24 119.5(3) . . ?
C26 C25 H25 120.3 . . ?
C24 C25 H25 120.3 . . ?
C25 C26 C27 121.1(3) . . ?
C25 C26 Cl1 120.0(3) . . ?
C27 C26 Cl1 118.9(3) . . ?
C26 C27 C28 119.3(3) . . ?
C26 C27 H27 120.3 . . ?
C28 C27 H27 120.3 . . ?
C27 C28 C23 121.2(3) . . ?
C27 C28 H28 119.4 . . ?
C23 C28 H28 119.4 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C12 N2 N3 C22 -167.5(2) . . . . ?
C13 N2 N3 C22 -0.1(3) . . . . ?
C9 O2 C1 C2 -179.8(2) . . . . ?
C9 O2 C1 C6 0.8(4) . . . . ?
O2 C1 C2 C3 179.8(2) . . . . ?
C6 C1 C2 C3 -0.8(4) . . . . ?
C1 C2 C3 C4 0.2(5) . . . . ?
C2 C3 C4 C5 0.7(5) . . . . ?
C3 C4 C5 C6 -0.8(5) . . . . ?
O2 C1 C6 C5 180.0(2) . . . . ?
C2 C1 C6 C5 0.6(4) . . . . ?
O2 C1 C6 C7 1.7(4) . . . . ?
C2 C1 C6 C7 -177.7(2) . . . . ?
C4 C5 C6 C1 0.2(4) . . . . ?
C4 C5 C6 C7 178.4(3) . . . . ?
C1 C6 C7 C8 -2.0(4) . . . . ?
C5 C6 C7 C8 179.8(3) . . . . ?
C6 C7 C8 C9 -0.1(4) . . . . ?
C6 C7 C8 C10 178.7(2) . . . . ?
C1 O2 C9 O1 177.5(2) . . . . ?
C1 O2 C9 C8 -2.9(3) . . . . ?
C7 C8 C9 O1 -178.0(3) . . . . ?
C10 C8 C9 O1 3.2(4) . . . . ?
C7 C8 C9 O2 2.5(3) . . . . ?
C10 C8 C9 O2 -176.4(2) . . . . ?
C12 N1 C10 C11 0.5(3) . . . . ?
C12 N1 C10 C8 -179.7(2) . . . . ?
C7 C8 C10 C11 172.1(3) . . . . ?
C9 C8 C10 C11 -9.1(4) . . . . ?
C7 C8 C10 N1 -7.7(4) . . . . ?
C9 C8 C10 N1 171.2(2) . . . . ?
N1 C10 C11 S1 0.1(3) . . . . ?
C8 C10 C11 S1 -179.73(19) . . . . ?
C12 S1 C11 C10 -0.4(2) . . . . ?
C10 N1 C12 N2 176.5(2) . . . . ?
C10 N1 C12 S1 -0.9(3) . . . . ?
N3 N2 C12 N1 174.7(2) . . . . ?
C13 N2 C12 N1 9.0(4) . . . . ?
N3 N2 C12 S1 -8.0(3) . . . . ?
C13 N2 C12 S1 -173.7(2) . . . . ?
C11 S1 C12 N1 0.8(2) . . . . ?
C11 S1 C12 N2 -176.7(2) . . . . ?
C12 N2 C13 C14 -73.1(3) . . . . ?
N3 N2 C13 C14 120.7(2) . . . . ?
C12 N2 C13 C21 165.6(3) . . . . ?
N3 N2 C13 C21 -0.6(3) . . . . ?
N2 C13 C14 C15 152.8(2) . . . . ?
C21 C13 C14 C15 -93.3(3) . . . . ?
N2 C13 C14 C19 -30.4(3) . . . . ?
C21 C13 C14 C19 83.4(3) . . . . ?
C19 C14 C15 C16 0.9(4) . . . . ?
C13 C14 C15 C16 177.8(2) . . . . ?
C14 C15 C16 C17 -0.2(5) . . . . ?
C15 C16 C17 C18 -0.8(5) . . . . ?
C15 C16 C17 C20 178.7(3) . . . . ?
C16 C17 C18 C19 1.2(5) . . . . ?
C20 C17 C18 C19 -178.2(3) . . . . ?
C15 C14 C19 C18 -0.4(4) . . . . ?
C13 C14 C19 C18 -177.3(3) . . . . ?
C17 C18 C19 C14 -0.6(5) . . . . ?
N2 C13 C21 C22 1.0(3) . . . . ?
C14 C13 C21 C22 -120.0(2) . . . . ?
N2 N3 C22 C23 -176.7(2) . . . . ?
N2 N3 C22 C21 0.9(3) . . . . ?
C13 C21 C22 N3 -1.3(3) . . . . ?
C13 C21 C22 C23 176.2(2) . . . . ?
N3 C22 C23 C28 9.7(4) . . . . ?
C21 C22 C23 C28 -167.7(3) . . . . ?
N3 C22 C23 C24 -171.4(2) . . . . ?
C21 C22 C23 C24 11.3(4) . . . . ?
C28 C23 C24 C25 -0.1(4) . . . . ?
C22 C23 C24 C25 -179.1(2) . . . . ?
C23 C24 C25 C26 0.9(4) . . . . ?
C24 C25 C26 C27 -0.8(5) . . . . ?
C24 C25 C26 Cl1 179.1(2) . . . . ?
C25 C26 C27 C28 -0.1(5) . . . . ?
Cl1 C26 C27 C28 180.0(2) . . . . ?
C26 C27 C28 C23 0.9(5) . . . . ?
C24 C23 C28 C27 -0.8(4) . . . . ?
C22 C23 C28 C27 178.2(3) . . . . ?

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
C11 H11 O1 0.93 2.26 2.820(3) 118.3 . yes
C11 H11 O1 0.93 2.50 3.245(3) 137.3 2_665 yes
C21 H21B O1 0.97 2.28 3.191(3) 156.3 1_545 yes

_refine_diff_density_max         0.277
_refine_diff_density_min         -0.340
_refine_diff_density_rms         0.036

####################################################################### 
# 
# 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_A14
_database_code_depnum_ccdc_archive 'CCDC 981487'
loop_
_audit_author_name
_audit_author_address
'Muhammad Nawaz Tahir'
;University of Sargodha, Pakistan
Pakistan
;
_audit_update_record             
;
2020-05-19 deposited with the CCDC.	2020-07-29 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        
;
3-[2-(3,5-Di(4-chlorophenyl)-4,5-dihydro-1H-pyrazol-1-yl)-1,3-thiazol-4-yl]-2H
-1-benzopyran-2-one
;
_chemical_formula_moiety         'C27 H17 Cl2 N3 O2 S'
_chemical_formula_sum            'C27 H17 Cl2 N3 O2 S'
_chemical_formula_iupac          'C27 H17 Cl2 N3 O2 S'
_chemical_formula_weight         518.40

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      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                   8.6740(6)
_cell_length_b                   11.8234(8)
_cell_length_c                   12.4070(7)
_cell_angle_alpha                71.363(2)
_cell_angle_beta                 73.094(3)
_cell_angle_gamma                82.970(3)
_cell_volume                     1152.98(13)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    4265
_cell_measurement_theta_min      1.798
_cell_measurement_theta_max      27.271
_cell_measurement_temperature    296(2)
_exptl_crystal_description       prism
_exptl_crystal_colour            'light yellow'
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.24
_exptl_crystal_density_diffrn    1.493
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             532
_exptl_absorpt_coefficient_mu    0.405
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2005)'
_exptl_absorpt_correction_T_min  0.680
_exptl_absorpt_correction_T_max  0.746
_shelx_estimated_absorpt_T_min   0.861
_shelx_estimated_absorpt_T_max   0.909
_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 7.76
_diffrn_reflns_number            18290
_diffrn_reflns_av_unetI/netI     0.0232
_diffrn_reflns_av_R_equivalents  0.0252
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         1.798
_diffrn_reflns_theta_max         27.271
_diffrn_reflns_theta_full        27.271
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measured_fraction_theta_full 0.987
_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             5105
_reflns_number_gt                4265
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0483
_refine_ls_R_factor_gt           0.0392
_refine_ls_wR_factor_ref         0.1074
_refine_ls_wR_factor_gt          0.1010
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_restrained_S_all      1.045
_refine_ls_number_reflns         5105
_refine_ls_number_parameters     316
_refine_ls_number_restraints     0
_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)+(0.0491P)²+0.4013P] 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

_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 0.00106(8) 0.59685(6) 0.22735(8) 0.0992(3) Uani 1 1 d . . . . .
Cl2 Cl 0.61166(7) 0.40265(5) -0.69677(4) 0.06005(16) Uani 1 1 d . . . . .
S1 S 0.17162(6) -0.01952(4) 0.06515(4) 0.04332(13) Uani 1 1 d . . . . .
O1 O -0.04696(16) -0.22480(12) 0.45054(11) 0.0507(3) Uani 1 1 d . . . . .
O2 O 0.02261(14) -0.20632(10) 0.59971(10) 0.0401(3) Uani 1 1 d . . . . .
N1 N 0.28047(16) 0.04710(11) 0.20787(11) 0.0353(3) Uani 1 1 d . . . . .
N2 N 0.3748(2) 0.15675(13) 0.00916(12) 0.0486(4) Uani 1 1 d . . . . .
N3 N 0.37934(19) 0.17067(13) -0.10646(12) 0.0433(3) Uani 1 1 d . . . . .
C1 C 0.11111(19) -0.15749(14) 0.64804(14) 0.0350(3) Uani 1 1 d . . . . .
C2 C 0.0841(2) -0.19802(16) 0.76985(15) 0.0431(4) Uani 1 1 d . . . . .
H2 H 0.008614 -0.255795 0.816177 0.052 Uiso 1 1 calc R U . . .
C3 C 0.1716(2) -0.15055(17) 0.82004(15) 0.0478(4) Uani 1 1 d . . . . .
H3 H 0.155499 -0.177029 0.901483 0.057 Uiso 1 1 calc R U . . .
C4 C 0.2837(2) -0.06381(17) 0.75168(16) 0.0488(4) Uani 1 1 d . . . . .
H4 H 0.341723 -0.032443 0.787254 0.059 Uiso 1 1 calc R U . . .
C5 C 0.3088(2) -0.02429(16) 0.63090(15) 0.0430(4) Uani 1 1 d . . . . .
H5 H 0.383649 0.034074 0.585137 0.052 Uiso 1 1 calc R U . . .
C6 C 0.22263(19) -0.07125(14) 0.57670(14) 0.0345(3) Uani 1 1 d . . . . .
C7 C 0.24054(19) -0.03523(14) 0.45210(14) 0.0345(3) Uani 1 1 d . . . . .
H7 H 0.313438 0.023417 0.403020 0.041 Uiso 1 1 calc R U . . .
C8 C 0.15509(18) -0.08359(13) 0.40353(13) 0.0320(3) Uani 1 1 d . . . . .
C9 C 0.03797(19) -0.17461(14) 0.48034(14) 0.0362(3) Uani 1 1 d . . . . .
C10 C 0.17666(18) -0.04626(13) 0.27567(13) 0.0324(3) Uani 1 1 d . . . . .
C11 C 0.1087(2) -0.09204(15) 0.21418(14) 0.0398(4) Uani 1 1 d . . . . .
H11 H 0.037421 -0.154405 0.247850 0.048 Uiso 1 1 calc R U . . .
C12 C 0.28664(19) 0.06910(14) 0.09754(14) 0.0355(3) Uani 1 1 d . . . . .
C13 C 0.4628(2) 0.24829(15) 0.02289(14) 0.0402(4) Uani 1 1 d . . . . .
H13 H 0.534199 0.210234 0.073691 0.048 Uiso 1 1 calc R U . . .
C14 C 0.3483(2) 0.33714(15) 0.07309(14) 0.0383(4) Uani 1 1 d . . . . .
C15 C 0.2682(2) 0.42629(18) 0.00344(17) 0.0522(5) Uani 1 1 d . . . . .
H15 H 0.285762 0.432068 -0.075702 0.063 Uiso 1 1 calc R U . . .
C16 C 0.1625(3) 0.50677(19) 0.0507(2) 0.0616(5) Uani 1 1 d . . . . .
H16 H 0.110170 0.567083 0.003572 0.074 Uiso 1 1 calc R U . . .
C17 C 0.1360(2) 0.49625(19) 0.1679(2) 0.0590(5) Uani 1 1 d . . . . .
C18 C 0.2125(3) 0.40951(18) 0.23857(18) 0.0582(5) Uani 1 1 d . . . . .
H18 H 0.193398 0.403651 0.317871 0.070 Uiso 1 1 calc R U . . .
C19 C 0.3185(2) 0.33059(16) 0.19045(15) 0.0486(4) Uani 1 1 d . . . . .
H19 H 0.371393 0.271455 0.238208 0.058 Uiso 1 1 calc R U . . .
C20 C 0.5627(2) 0.29938(16) -0.10531(15) 0.0433(4) Uani 1 1 d . . . . .
H20A H 0.558086 0.386006 -0.130060 0.052 Uiso 1 1 calc R U . . .
H20B H 0.674410 0.271505 -0.115376 0.052 Uiso 1 1 calc R U . . .
C21 C 0.4813(2) 0.25113(15) -0.17296(14) 0.0388(4) Uani 1 1 d . . . . .
C22 C 0.5124(2) 0.28850(14) -0.30125(14) 0.0382(4) Uani 1 1 d . . . . .
C23 C 0.4068(2) 0.26177(16) -0.35451(15) 0.0453(4) Uani 1 1 d . . . . .
H23 H 0.314790 0.219689 -0.307702 0.054 Uiso 1 1 calc R U . . .
C24 C 0.4364(2) 0.29669(16) -0.47565(16) 0.0479(4) Uani 1 1 d . . . . .
H24 H 0.365216 0.278489 -0.510664 0.057 Uiso 1 1 calc R U . . .
C25 C 0.5734(2) 0.35912(15) -0.54418(14) 0.0419(4) Uani 1 1 d . . . . .
C26 C 0.6793(2) 0.38776(16) -0.49466(15) 0.0453(4) Uani 1 1 d . . . . .
H26 H 0.770840 0.430085 -0.542133 0.054 Uiso 1 1 calc R U . . .
C27 C 0.6481(2) 0.35281(15) -0.37273(15) 0.0423(4) Uani 1 1 d . . . . .
H27 H 0.718883 0.372659 -0.338374 0.051 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 C17 1.745(2) . ?
Cl2 C25 1.7359(17) . ?
S1 C11 1.7223(17) . ?
S1 C12 1.7358(17) . ?
O1 C9 1.199(2) . ?
O2 C1 1.371(2) . ?
O2 C9 1.3764(19) . ?
N1 C12 1.295(2) . ?
N1 C10 1.395(2) . ?
N2 C12 1.357(2) . ?
N2 N3 1.3799(19) . ?
N2 C13 1.476(2) . ?
N3 C21 1.284(2) . ?
C1 C6 1.388(2) . ?
C1 C2 1.388(2) . ?
C2 C3 1.372(3) . ?
C2 H2 0.9300 . ?
C3 C4 1.388(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.378(2) . ?
C4 H4 0.9300 . ?
C5 C6 1.397(2) . ?
C5 H5 0.9300 . ?
C6 C7 1.432(2) . ?
C7 C8 1.350(2) . ?
C7 H7 0.9300 . ?
C8 C10 1.465(2) . ?
C8 C9 1.465(2) . ?
C10 C11 1.351(2) . ?
C11 H11 0.9300 . ?
C13 C14 1.510(2) . ?
C13 C20 1.536(2) . ?
C13 H13 0.9800 . ?
C14 C19 1.381(2) . ?
C14 C15 1.388(2) . ?
C15 C16 1.386(3) . ?
C15 H15 0.9300 . ?
C16 C17 1.371(3) . ?
C16 H16 0.9300 . ?
C17 C18 1.363(3) . ?
C18 C19 1.378(3) . ?
C18 H18 0.9300 . ?
C19 H19 0.9300 . ?
C20 C21 1.509(2) . ?
C20 H20A 0.9700 . ?
C20 H20B 0.9700 . ?
C21 C22 1.460(2) . ?
C22 C27 1.390(2) . ?
C22 C23 1.390(3) . ?
C23 C24 1.379(2) . ?
C23 H23 0.9300 . ?
C24 C25 1.381(3) . ?
C24 H24 0.9300 . ?
C25 C26 1.368(3) . ?
C26 C27 1.386(2) . ?
C26 H26 0.9300 . ?
C27 H27 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
C11 S1 C12 87.95(8) . . ?
C1 O2 C9 123.21(12) . . ?
C12 N1 C10 109.34(13) . . ?
C12 N2 N3 119.78(14) . . ?
C12 N2 C13 126.39(14) . . ?
N3 N2 C13 113.71(13) . . ?
C21 N3 N2 107.73(14) . . ?
O2 C1 C6 120.58(14) . . ?
O2 C1 C2 117.24(15) . . ?
C6 C1 C2 122.17(16) . . ?
C3 C2 C1 118.21(17) . . ?
C3 C2 H2 120.9 . . ?
C1 C2 H2 120.9 . . ?
C2 C3 C4 121.29(16) . . ?
C2 C3 H3 119.4 . . ?
C4 C3 H3 119.4 . . ?
C5 C4 C3 119.78(17) . . ?
C5 C4 H4 120.1 . . ?
C3 C4 H4 120.1 . . ?
C4 C5 C6 120.49(17) . . ?
C4 C5 H5 119.8 . . ?
C6 C5 H5 119.8 . . ?
C1 C6 C5 118.06(15) . . ?
C1 C6 C7 117.69(15) . . ?
C5 C6 C7 124.25(15) . . ?
C8 C7 C6 122.18(14) . . ?
C8 C7 H7 118.9 . . ?
C6 C7 H7 118.9 . . ?
C7 C8 C10 121.24(14) . . ?
C7 C8 C9 119.31(14) . . ?
C10 C8 C9 119.46(14) . . ?
O1 C9 O2 115.99(14) . . ?
O1 C9 C8 126.99(15) . . ?
O2 C9 C8 117.02(14) . . ?
C11 C10 N1 115.28(14) . . ?
C11 C10 C8 127.82(14) . . ?
N1 C10 C8 116.90(13) . . ?
C10 C11 S1 110.98(12) . . ?
C10 C11 H11 124.5 . . ?
S1 C11 H11 124.5 . . ?
N1 C12 N2 123.77(15) . . ?
N1 C12 S1 116.45(12) . . ?
N2 C12 S1 119.78(12) . . ?
N2 C13 C14 111.37(14) . . ?
N2 C13 C20 99.86(13) . . ?
C14 C13 C20 114.89(14) . . ?
N2 C13 H13 110.1 . . ?
C14 C13 H13 110.1 . . ?
C20 C13 H13 110.1 . . ?
C19 C14 C15 118.16(17) . . ?
C19 C14 C13 120.67(15) . . ?
C15 C14 C13 121.16(15) . . ?
C16 C15 C14 120.65(19) . . ?
C16 C15 H15 119.7 . . ?
C14 C15 H15 119.7 . . ?
C17 C16 C15 119.1(2) . . ?
C17 C16 H16 120.5 . . ?
C15 C16 H16 120.5 . . ?
C18 C17 C16 121.60(19) . . ?
C18 C17 Cl1 119.50(18) . . ?
C16 C17 Cl1 118.90(19) . . ?
C17 C18 C19 118.85(19) . . ?
C17 C18 H18 120.6 . . ?
C19 C18 H18 120.6 . . ?
C18 C19 C14 121.64(18) . . ?
C18 C19 H19 119.2 . . ?
C14 C19 H19 119.2 . . ?
C21 C20 C13 102.70(13) . . ?
C21 C20 H20A 111.2 . . ?
C13 C20 H20A 111.2 . . ?
C21 C20 H20B 111.2 . . ?
C13 C20 H20B 111.2 . . ?
H20A C20 H20B 109.1 . . ?
N3 C21 C22 121.41(16) . . ?
N3 C21 C20 113.42(14) . . ?
C22 C21 C20 125.17(15) . . ?
C27 C22 C23 118.59(15) . . ?
C27 C22 C21 120.43(16) . . ?
C23 C22 C21 120.98(15) . . ?
C24 C23 C22 121.00(17) . . ?
C24 C23 H23 119.5 . . ?
C22 C23 H23 119.5 . . ?
C23 C24 C25 118.96(18) . . ?
C23 C24 H24 120.5 . . ?
C25 C24 H24 120.5 . . ?
C26 C25 C24 121.58(16) . . ?
C26 C25 Cl2 119.32(14) . . ?
C24 C25 Cl2 119.10(15) . . ?
C25 C26 C27 119.08(17) . . ?
C25 C26 H26 120.5 . . ?
C27 C26 H26 120.5 . . ?
C26 C27 C22 120.80(17) . . ?
C26 C27 H27 119.6 . . ?
C22 C27 H27 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
C12 N2 N3 C21 -174.15(16) . . . . ?
C13 N2 N3 C21 9.6(2) . . . . ?
C9 O2 C1 C6 0.3(2) . . . . ?
C9 O2 C1 C2 -179.71(14) . . . . ?
O2 C1 C2 C3 179.85(15) . . . . ?
C6 C1 C2 C3 -0.1(2) . . . . ?
C1 C2 C3 C4 0.4(3) . . . . ?
C2 C3 C4 C5 -0.2(3) . . . . ?
C3 C4 C5 C6 -0.2(3) . . . . ?
O2 C1 C6 C5 179.71(14) . . . . ?
C2 C1 C6 C5 -0.3(2) . . . . ?
O2 C1 C6 C7 0.4(2) . . . . ?
C2 C1 C6 C7 -179.65(14) . . . . ?
C4 C5 C6 C1 0.5(2) . . . . ?
C4 C5 C6 C7 179.78(15) . . . . ?
C1 C6 C7 C8 -1.0(2) . . . . ?
C5 C6 C7 C8 179.67(15) . . . . ?
C6 C7 C8 C10 -179.34(13) . . . . ?
C6 C7 C8 C9 1.0(2) . . . . ?
C1 O2 C9 O1 179.86(14) . . . . ?
C1 O2 C9 C8 -0.3(2) . . . . ?
C7 C8 C9 O1 179.48(16) . . . . ?
C10 C8 C9 O1 -0.2(2) . . . . ?
C7 C8 C9 O2 -0.4(2) . . . . ?
C10 C8 C9 O2 180.00(13) . . . . ?
C12 N1 C10 C11 0.36(19) . . . . ?
C12 N1 C10 C8 179.89(13) . . . . ?
C7 C8 C10 C11 175.00(16) . . . . ?
C9 C8 C10 C11 -5.4(2) . . . . ?
C7 C8 C10 N1 -4.5(2) . . . . ?
C9 C8 C10 N1 175.18(13) . . . . ?
N1 C10 C11 S1 -0.07(18) . . . . ?
C8 C10 C11 S1 -179.55(12) . . . . ?
C12 S1 C11 C10 -0.16(13) . . . . ?
C10 N1 C12 N2 178.63(15) . . . . ?
C10 N1 C12 S1 -0.50(17) . . . . ?
N3 N2 C12 N1 177.39(15) . . . . ?
C13 N2 C12 N1 -6.8(3) . . . . ?
N3 N2 C12 S1 -3.5(2) . . . . ?
C13 N2 C12 S1 172.27(14) . . . . ?
C11 S1 C12 N1 0.40(13) . . . . ?
C11 S1 C12 N2 -178.76(15) . . . . ?
C12 N2 C13 C14 -69.8(2) . . . . ?
N3 N2 C13 C14 106.23(17) . . . . ?
C12 N2 C13 C20 168.44(17) . . . . ?
N3 N2 C13 C20 -15.55(19) . . . . ?
N2 C13 C14 C19 102.62(18) . . . . ?
C20 C13 C14 C19 -144.79(16) . . . . ?
N2 C13 C14 C15 -76.4(2) . . . . ?
C20 C13 C14 C15 36.2(2) . . . . ?
C19 C14 C15 C16 0.5(3) . . . . ?
C13 C14 C15 C16 179.51(17) . . . . ?
C14 C15 C16 C17 -0.9(3) . . . . ?
C15 C16 C17 C18 0.7(3) . . . . ?
C15 C16 C17 Cl1 -179.32(16) . . . . ?
C16 C17 C18 C19 -0.1(3) . . . . ?
Cl1 C17 C18 C19 179.91(15) . . . . ?
C17 C18 C19 C14 -0.3(3) . . . . ?
C15 C14 C19 C18 0.1(3) . . . . ?
C13 C14 C19 C18 -178.91(17) . . . . ?
N2 C13 C20 C21 14.52(16) . . . . ?
C14 C13 C20 C21 -104.70(16) . . . . ?
N2 N3 C21 C22 -178.94(15) . . . . ?
N2 N3 C21 C20 1.6(2) . . . . ?
C13 C20 C21 N3 -11.1(2) . . . . ?
C13 C20 C21 C22 169.48(15) . . . . ?
N3 C21 C22 C27 -164.35(16) . . . . ?
C20 C21 C22 C27 15.1(3) . . . . ?
N3 C21 C22 C23 16.3(3) . . . . ?
C20 C21 C22 C23 -164.31(17) . . . . ?
C27 C22 C23 C24 0.8(3) . . . . ?
C21 C22 C23 C24 -179.79(16) . . . . ?
C22 C23 C24 C25 0.0(3) . . . . ?
C23 C24 C25 C26 -0.5(3) . . . . ?
C23 C24 C25 Cl2 179.70(13) . . . . ?
C24 C25 C26 C27 0.2(3) . . . . ?
Cl2 C25 C26 C27 179.97(13) . . . . ?
C25 C26 C27 C22 0.7(3) . . . . ?
C23 C22 C27 C26 -1.2(2) . . . . ?
C21 C22 C27 C26 179.45(15) . . . . ?

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
C11 H11 O1 0.93 2.30 2.857(2) 117.9 . yes

_refine_diff_density_max         0.476
_refine_diff_density_min         -0.589
_refine_diff_density_rms         0.055

