# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2022

####################################################################### 
# 
# 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_4a
_database_code_depnum_ccdc_archive 'CCDC 2158357'
loop_
_audit_author_name
_audit_author_address
'Dr. Gamidi Rama Krishna'
;Ramanujan Fellow CSIR National Chemical Laboratory
India
;

_audit_update_record             
;
2022-03-14 deposited with the CCDC.	2022-04-13 downloaded from the CCDC.
;
# publcif _publ_body_element loop end

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        2-Phenyl-3-tosylpyrazolo[1,5-a]pyridine
_chemical_name_common            3-sulfonyl-pyrazolo[1,5-a]pyridines
_chemical_melting_point          134(2)
_chemical_formula_moiety         'C20 H16 N2 O2 S'
_chemical_formula_sum            'C20 H16 N2 O2 S'
_chemical_formula_weight         348.41

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

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

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

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

_cell_length_a                   8.6434(13)
_cell_length_b                   12.8669(18)
_cell_length_c                   15.514(3)
_cell_angle_alpha                90
_cell_angle_beta                 99.534(8)
_cell_angle_gamma                90
_cell_volume                     1701.5(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9585
_cell_measurement_theta_min      2.99
_cell_measurement_theta_max      27.52

_exptl_crystal_description       Plate
_exptl_crystal_colour            Colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.360
_exptl_crystal_F_000             728
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.1
_exptl_absorpt_coefficient_mu    0.206
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6990
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   'SADABS; Bruker, 2016'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker D8 VENTURE Kappa Duo PHOTON II CPAD'
_diffrn_measurement_method       '\ f and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            61862
_diffrn_reflns_av_unetI/netI     0.0138
_diffrn_reflns_av_R_equivalents  0.0377
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         2.068
_diffrn_reflns_theta_max         27.000
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.962
_diffrn_measured_fraction_theta_full 0.955
_diffrn_reflns_Laue_measured_fraction_max 0.962
_diffrn_reflns_Laue_measured_fraction_full 0.955
_diffrn_reflns_point_group_measured_fraction_max 0.962
_diffrn_reflns_point_group_measured_fraction_full 0.955
_reflns_number_total             3563
_reflns_number_gt                3520
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker APEX3'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0599P)²+0.7013P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_extinction_coef       0.253(17)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3563
_refine_ls_number_parameters     228
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0368
_refine_ls_R_factor_gt           0.0344
_refine_ls_wR_factor_ref         0.1105
_refine_ls_wR_factor_gt          0.0966
_refine_ls_goodness_of_fit_ref   1.164
_refine_ls_restrained_S_all      1.164
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.19987(15) 0.42884(10) 0.43711(8) 0.0192(3) Uani 1 1 d . . . . .
H1 H 0.1142 0.4027 0.4618 0.023 Uiso 1 1 calc R U . . .
C2 C 0.27729(17) 0.36707(10) 0.38714(9) 0.0225(3) Uani 1 1 d . . . . .
H2 H 0.2449 0.2971 0.3760 0.027 Uiso 1 1 calc R U . . .
C3 C 0.40656(17) 0.40713(11) 0.35161(9) 0.0241(3) Uani 1 1 d . . . . .
H3 H 0.4601 0.3634 0.3170 0.029 Uiso 1 1 calc R U . . .
C4 C 0.45513(16) 0.50799(11) 0.36657(9) 0.0212(3) Uani 1 1 d . . . . .
H4 H 0.5423 0.5340 0.3432 0.025 Uiso 1 1 calc R U . . .
C5 C 0.37276(14) 0.57281(10) 0.41763(8) 0.0170(3) Uani 1 1 d . . . . .
C6 C 0.37880(15) 0.67691(10) 0.44601(8) 0.0173(3) Uani 1 1 d . . . . .
C7 C 0.25363(14) 0.68820(10) 0.49389(8) 0.0160(3) Uani 1 1 d . . . . .
C8 C 0.19555(16) 0.78068(10) 0.53507(8) 0.0170(3) Uani 1 1 d . . . . .
C9 C 0.29521(16) 0.84342(11) 0.59333(9) 0.0213(3) Uani 1 1 d . . . . .
H9 H 0.4044 0.8289 0.6054 0.026 Uiso 1 1 calc R U . . .
C10 C 0.23443(18) 0.92737(11) 0.63366(9) 0.0245(3) Uani 1 1 d . . . . .
H10 H 0.3024 0.9697 0.6735 0.029 Uiso 1 1 calc R U . . .
C11 C 0.07516(18) 0.94949(11) 0.61600(9) 0.0245(3) Uani 1 1 d . . . . .
H11 H 0.0344 1.0068 0.6437 0.029 Uiso 1 1 calc R U . . .
C12 C -0.02495(17) 0.88762(11) 0.55765(10) 0.0234(3) Uani 1 1 d . . . . .
H12 H -0.1339 0.9029 0.5454 0.028 Uiso 1 1 calc R U . . .
C13 C 0.03465(15) 0.80359(10) 0.51738(9) 0.0192(3) Uani 1 1 d . . . . .
H13 H -0.0338 0.7615 0.4777 0.023 Uiso 1 1 calc R U . . .
C14 C 0.37768(14) 0.86109(10) 0.35230(8) 0.0166(3) Uani 1 1 d . . . . .
C15 C 0.39160(15) 0.96616(10) 0.37276(8) 0.0185(3) Uani 1 1 d . . . . .
H15 H 0.4607 0.9889 0.4233 0.022 Uiso 1 1 calc R U . . .
C16 C 0.30269(15) 1.03756(10) 0.31811(9) 0.0199(3) Uani 1 1 d . . . . .
H16 H 0.3132 1.1096 0.3312 0.024 Uiso 1 1 calc R U . . .
C17 C 0.19841(15) 1.00536(11) 0.24454(9) 0.0200(3) Uani 1 1 d . . . . .
C18 C 0.18549(17) 0.89879(12) 0.22608(9) 0.0233(3) Uani 1 1 d . . . . .
H18 H 0.1147 0.8756 0.1763 0.028 Uiso 1 1 calc R U . . .
C19 C 0.27440(17) 0.82659(11) 0.27921(9) 0.0223(3) Uani 1 1 d . . . . .
H19 H 0.2651 0.7545 0.2660 0.027 Uiso 1 1 calc R U . . .
C20 C 0.10029(17) 1.08340(12) 0.18686(10) 0.0277(3) Uani 1 1 d . . . . .
H20A H -0.0056 1.0854 0.2017 0.042 Uiso 1 1 calc R U . . .
H20B H 0.0943 1.0631 0.1255 0.042 Uiso 1 1 calc R U . . .
H20C H 0.1485 1.1523 0.1959 0.042 Uiso 1 1 calc R U . . .
N1 N 0.17488(12) 0.59890(8) 0.49706(7) 0.0168(2) Uani 1 1 d . . . . .
N2 N 0.24871(12) 0.52983(8) 0.45086(7) 0.0159(2) Uani 1 1 d . . . . .
O1 O 0.59778(13) 0.72140(8) 0.35970(8) 0.0293(3) Uani 1 1 d . . . . .
O2 O 0.58175(11) 0.82640(8) 0.49176(7) 0.0245(2) Uani 1 1 d . . . . .
S1 S 0.50305(3) 0.77142(2) 0.41594(2) 0.01841(15) Uani 1 1 d . . . . .


_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
C1 C2 1.3611(19) . ?
C1 N2 1.3721(17) . ?
C1 H1 0.9500 . ?
C2 C3 1.422(2) . ?
C2 H2 0.9500 . ?
C3 C4 1.372(2) . ?
C3 H3 0.9500 . ?
C4 C5 1.4201(18) . ?
C4 H4 0.9500 . ?
C5 N2 1.3800(16) . ?
C5 C6 1.4082(18) . ?
C6 C7 1.4177(17) . ?
C6 S1 1.7366(13) . ?
C7 N1 1.3404(16) . ?
C7 C8 1.4772(17) . ?
C8 C9 1.3975(18) . ?
C8 C13 1.4035(18) . ?
C9 C10 1.3940(19) . ?
C9 H9 0.9500 . ?
C10 C11 1.388(2) . ?
C10 H10 0.9500 . ?
C11 C12 1.394(2) . ?
C11 H11 0.9500 . ?
C12 C13 1.3897(19) . ?
C12 H12 0.9500 . ?
C13 H13 0.9500 . ?
C14 C15 1.3893(18) . ?
C14 C19 1.3944(18) . ?
C14 S1 1.7679(13) . ?
C15 C16 1.3920(18) . ?
C15 H15 0.9500 . ?
C16 C17 1.3949(19) . ?
C16 H16 0.9500 . ?
C17 C18 1.402(2) . ?
C17 C20 1.5089(19) . ?
C18 C19 1.387(2) . ?
C18 H18 0.9500 . ?
C19 H19 0.9500 . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
N1 N2 1.3647(15) . ?
O1 S1 1.4431(11) . ?
O2 S1 1.4428(11) . ?

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
C2 C1 N2 118.29(12) . . ?
C2 C1 H1 120.9 . . ?
N2 C1 H1 120.9 . . ?
C1 C2 C3 120.07(13) . . ?
C1 C2 H2 120.0 . . ?
C3 C2 H2 120.0 . . ?
C4 C3 C2 121.03(13) . . ?
C4 C3 H3 119.5 . . ?
C2 C3 H3 119.5 . . ?
C3 C4 C5 118.84(12) . . ?
C3 C4 H4 120.6 . . ?
C5 C4 H4 120.6 . . ?
N2 C5 C6 104.78(11) . . ?
N2 C5 C4 117.73(12) . . ?
C6 C5 C4 137.48(12) . . ?
C5 C6 C7 105.62(11) . . ?
C5 C6 S1 125.07(10) . . ?
C7 C6 S1 128.95(10) . . ?
N1 C7 C6 111.57(11) . . ?
N1 C7 C8 117.62(11) . . ?
C6 C7 C8 130.74(12) . . ?
C9 C8 C13 119.33(12) . . ?
C9 C8 C7 121.86(12) . . ?
C13 C8 C7 118.77(12) . . ?
C10 C9 C8 120.01(13) . . ?
C10 C9 H9 120.0 . . ?
C8 C9 H9 120.0 . . ?
C11 C10 C9 120.37(13) . . ?
C11 C10 H10 119.8 . . ?
C9 C10 H10 119.8 . . ?
C10 C11 C12 119.99(13) . . ?
C10 C11 H11 120.0 . . ?
C12 C11 H11 120.0 . . ?
C13 C12 C11 119.99(13) . . ?
C13 C12 H12 120.0 . . ?
C11 C12 H12 120.0 . . ?
C12 C13 C8 120.31(12) . . ?
C12 C13 H13 119.8 . . ?
C8 C13 H13 119.8 . . ?
C15 C14 C19 121.00(12) . . ?
C15 C14 S1 119.05(10) . . ?
C19 C14 S1 119.80(10) . . ?
C14 C15 C16 119.00(12) . . ?
C14 C15 H15 120.5 . . ?
C16 C15 H15 120.5 . . ?
C15 C16 C17 121.28(12) . . ?
C15 C16 H16 119.4 . . ?
C17 C16 H16 119.4 . . ?
C16 C17 C18 118.46(12) . . ?
C16 C17 C20 120.74(13) . . ?
C18 C17 C20 120.80(12) . . ?
C19 C18 C17 121.09(12) . . ?
C19 C18 H18 119.5 . . ?
C17 C18 H18 119.5 . . ?
C18 C19 C14 119.16(12) . . ?
C18 C19 H19 120.4 . . ?
C14 C19 H19 120.4 . . ?
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 . . ?
C7 N1 N2 104.74(10) . . ?
N1 N2 C1 122.67(11) . . ?
N1 N2 C5 113.27(10) . . ?
C1 N2 C5 124.03(11) . . ?
O2 S1 O1 118.26(7) . . ?
O2 S1 C6 110.69(6) . . ?
O1 S1 C6 106.74(6) . . ?
O2 S1 C14 107.33(6) . . ?
O1 S1 C14 108.07(6) . . ?
C6 S1 C14 104.95(6) . . ?

_refine_diff_density_max         0.453
_refine_diff_density_min         -0.408
_refine_diff_density_rms         0.097




_publcif_funding_html            
;
;
