# 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 2023

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

data_shelx
_database_code_depnum_ccdc_archive 'CCDC 2179553'
loop_
_audit_author_name
_audit_author_address
'Snoxma Smile'
;CSIR CLRI
India
;
_audit_update_record             
;
2022-06-16 deposited with the CCDC.	2023-01-17 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        
(E)-4-methyl-N'-(1-methyl-2-oxoindolin-3-ylidene)-N-phenylbenzenesulfonohydrazide
_chemical_name_common            SS2-89F3
_chemical_melting_point          ?
_chemical_formula_moiety         'C22 H19 N3 O3 S'
_chemical_formula_sum            'C22 H19 N3 O3 S'
_chemical_formula_weight         405.46

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      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                   9.1555(6)
_cell_length_b                   10.4074(7)
_cell_length_c                   11.9079(7)
_cell_angle_alpha                103.303(2)
_cell_angle_beta                 99.290(2)
_cell_angle_gamma                112.822(2)
_cell_volume                     977.20(11)
_cell_formula_units_Z            2
_cell_measurement_temperature    298(2)

_cell_measurement_reflns_used    5468
_cell_measurement_theta_min      3.11
_cell_measurement_theta_max      26.40
_exptl_crystal_description       block
_exptl_crystal_colour            orange

_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.378
_exptl_crystal_F_000             424
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.238
_exptl_crystal_size_mid          0.117
_exptl_crystal_size_min          0.052
_exptl_absorpt_coefficient_mu    0.195
_shelx_estimated_absorpt_T_min   0.955
_shelx_estimated_absorpt_T_max   0.990
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.943
_exptl_absorpt_correction_T_max  0.986
_exptl_absorpt_process_details   'SADABS (Bruker, 2016)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a

_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  
'Bruker D8 VENTURE diffractometer with PHOTON II detector'
_diffrn_measurement_method       'ω and φ scan'


_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            30992
_diffrn_reflns_av_unetI/netI     0.0557
_diffrn_reflns_av_R_equivalents  0.1050
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_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         3.128
_diffrn_reflns_theta_max         26.484
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             4015
_reflns_number_gt                2773
_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       'APEX3 (Bruker, 2016)'
_computing_cell_refinement       'APEX3/SAINT (Bruker, 2016)'
_computing_data_reduction        'SAINT/XPREP (Bruker, 2016)'
_computing_structure_solution    'SHELXT-2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'ORTEP3 (Farrugia, 1997) '
_computing_publication_material  'SHELXL-2018/3 (Sheldrick, 2018)'



_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)+(0.0470P)²+0.3956P] 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     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4015
_refine_ls_number_parameters     264
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0846
_refine_ls_R_factor_gt           0.0511
_refine_ls_wR_factor_ref         0.1251
_refine_ls_wR_factor_gt          0.1096
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_restrained_S_all      1.027
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.1200(3) 0.0057(3) 0.1504(2) 0.0406(6) Uani 1 1 d . . . . .
C2 C 0.1144(4) -0.1265(3) 0.0878(3) 0.0570(8) Uani 1 1 d . . . . .
H2 H 0.052847 -0.213661 0.101147 0.068 Uiso 1 1 calc R U . . .
C3 C 0.2039(4) -0.1240(3) 0.0045(3) 0.0647(9) Uani 1 1 d . . . . .
H3 H 0.202914 -0.211370 -0.038236 0.078 Uiso 1 1 calc R U . . .
C4 C 0.2945(4) 0.0041(3) -0.0169(2) 0.0573(8) Uani 1 1 d . . . . .
H4 H 0.352113 0.001543 -0.074215 0.069 Uiso 1 1 calc R U . . .
C5 C 0.3008(3) 0.1373(3) 0.0462(2) 0.0432(6) Uani 1 1 d . . . . .
H5 H 0.361179 0.223725 0.031311 0.052 Uiso 1 1 calc R U . . .
C6 C 0.2146(3) 0.1380(2) 0.1319(2) 0.0351(5) Uani 1 1 d . . . . .
C7 C 0.1850(3) 0.2519(3) 0.2086(2) 0.0338(5) Uani 1 1 d . . . . .
C8 C 0.0638(3) 0.1745(3) 0.2724(2) 0.0422(6) Uani 1 1 d . . . . .
C9 C -0.0714(4) -0.0810(4) 0.2781(3) 0.0715(9) Uani 1 1 d . . . . .
H9A H -0.108463 -0.035412 0.339634 0.107 Uiso 1 1 calc R U . . .
H9B H -0.012281 -0.129119 0.310252 0.107 Uiso 1 1 calc R U . . .
H9C H -0.164917 -0.152191 0.212203 0.107 Uiso 1 1 calc R U . . .
C10 C 0.5227(3) 0.4704(2) 0.2334(2) 0.0352(5) Uani 1 1 d . . . . .
C11 C 0.5682(3) 0.4747(3) 0.3515(2) 0.0434(6) Uani 1 1 d . . . . .
H11 H 0.495754 0.470803 0.398534 0.052 Uiso 1 1 calc R U . . .
C12 C 0.7218(4) 0.4849(3) 0.3989(3) 0.0574(8) Uani 1 1 d . . . . .
H12 H 0.754792 0.491433 0.478883 0.069 Uiso 1 1 calc R U . . .
C13 C 0.8265(4) 0.4854(3) 0.3269(3) 0.0651(9) Uani 1 1 d . . . . .
H13 H 0.927960 0.488027 0.357842 0.078 Uiso 1 1 calc R U . . .
C14 C 0.7814(4) 0.4820(3) 0.2102(3) 0.0596(8) Uani 1 1 d . . . . .
H14 H 0.853385 0.484213 0.162935 0.072 Uiso 1 1 calc R U . . .
C15 C 0.6291(3) 0.4751(3) 0.1625(2) 0.0457(6) Uani 1 1 d . . . . .
H15 H 0.598864 0.473799 0.083690 0.055 Uiso 1 1 calc R U . . .
C16 C 0.3862(3) 0.7197(2) 0.3324(2) 0.0333(5) Uani 1 1 d . . . . .
C17 C 0.2497(3) 0.7217(3) 0.3664(2) 0.0385(6) Uani 1 1 d . . . . .
H17 H 0.147446 0.678799 0.309712 0.046 Uiso 1 1 calc R U . . .
C18 C 0.2663(3) 0.7878(3) 0.4855(2) 0.0414(6) Uani 1 1 d . . . . .
H18 H 0.174530 0.789927 0.508192 0.050 Uiso 1 1 calc R U . . .
C19 C 0.4167(3) 0.8509(3) 0.5718(2) 0.0378(6) Uani 1 1 d . . . . .
C20 C 0.5532(3) 0.8499(3) 0.5348(2) 0.0407(6) Uani 1 1 d . . . . .
H20 H 0.655585 0.893279 0.591435 0.049 Uiso 1 1 calc R U . . .
C21 C 0.5399(3) 0.7862(3) 0.4162(2) 0.0387(6) Uani 1 1 d . . . . .
H21 H 0.632391 0.787675 0.392674 0.046 Uiso 1 1 calc R U . . .
C22 C 0.4308(4) 0.9142(3) 0.7020(2) 0.0526(7) Uani 1 1 d . . . . .
H22A H 0.351983 0.953198 0.708422 0.079 Uiso 1 1 calc R U . . .
H22B H 0.540140 0.991535 0.741896 0.079 Uiso 1 1 calc R U . . .
H22C H 0.409148 0.838324 0.738816 0.079 Uiso 1 1 calc R U . . .
N1 N 0.2351(2) 0.3906(2) 0.23270(17) 0.0368(5) Uani 1 1 d . . . . .
N2 N 0.3627(2) 0.4622(2) 0.18221(16) 0.0347(5) Uani 1 1 d . . . . .
N3 N 0.0367(3) 0.0306(2) 0.2363(2) 0.0455(5) Uani 1 1 d . . . . .
O1 O 0.2015(2) 0.5881(2) 0.11110(15) 0.0533(5) Uani 1 1 d . . . . .
O2 O 0.5049(2) 0.7011(2) 0.14709(16) 0.0507(5) Uani 1 1 d . . . . .
O3 O 0.0072(3) 0.2284(2) 0.34410(19) 0.0639(6) Uani 1 1 d . . . . .
S1 S 0.36204(8) 0.62583(7) 0.18248(5) 0.03845(18) 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 1.383(4) . ?
C1 C6 1.404(3) . ?
C1 N3 1.406(3) . ?
C2 C3 1.383(4) . ?
C2 H2 0.9300 . ?
C3 C4 1.378(5) . ?
C3 H3 0.9300 . ?
C4 C5 1.391(4) . ?
C4 H4 0.9300 . ?
C5 C6 1.388(3) . ?
C5 H5 0.9300 . ?
C6 C7 1.464(3) . ?
C7 N1 1.277(3) . ?
C7 C8 1.523(3) . ?
C8 O3 1.208(3) . ?
C8 N3 1.368(3) . ?
C9 N3 1.453(3) . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C10 C15 1.383(3) . ?
C10 C11 1.386(3) . ?
C10 N2 1.454(3) . ?
C11 C12 1.381(4) . ?
C11 H11 0.9300 . ?
C12 C13 1.384(4) . ?
C12 H12 0.9300 . ?
C13 C14 1.372(5) . ?
C13 H13 0.9300 . ?
C14 C15 1.386(4) . ?
C14 H14 0.9300 . ?
C15 H15 0.9300 . ?
C16 C17 1.381(3) . ?
C16 C21 1.388(3) . ?
C16 S1 1.758(2) . ?
C17 C18 1.381(3) . ?
C17 H17 0.9300 . ?
C18 C19 1.383(3) . ?
C18 H18 0.9300 . ?
C19 C20 1.393(3) . ?
C19 C22 1.501(3) . ?
C20 C21 1.379(3) . ?
C20 H20 0.9300 . ?
C21 H21 0.9300 . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?
N1 N2 1.428(3) . ?
N2 S1 1.705(2) . ?
O1 S1 1.4260(19) . ?
O2 S1 1.4272(18) . ?

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 C6 121.5(3) . . ?
C2 C1 N3 128.0(3) . . ?
C6 C1 N3 110.4(2) . . ?
C1 C2 C3 117.4(3) . . ?
C1 C2 H2 121.3 . . ?
C3 C2 H2 121.3 . . ?
C4 C3 C2 121.9(3) . . ?
C4 C3 H3 119.1 . . ?
C2 C3 H3 119.1 . . ?
C3 C4 C5 120.9(3) . . ?
C3 C4 H4 119.6 . . ?
C5 C4 H4 119.6 . . ?
C6 C5 C4 118.3(3) . . ?
C6 C5 H5 120.9 . . ?
C4 C5 H5 120.9 . . ?
C5 C6 C1 120.0(2) . . ?
C5 C6 C7 133.5(2) . . ?
C1 C6 C7 106.3(2) . . ?
N1 C7 C6 136.4(2) . . ?
N1 C7 C8 117.3(2) . . ?
C6 C7 C8 106.2(2) . . ?
O3 C8 N3 126.3(2) . . ?
O3 C8 C7 127.8(2) . . ?
N3 C8 C7 105.8(2) . . ?
N3 C9 H9A 109.5 . . ?
N3 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
N3 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C15 C10 C11 120.6(2) . . ?
C15 C10 N2 118.8(2) . . ?
C11 C10 N2 120.6(2) . . ?
C12 C11 C10 119.6(3) . . ?
C12 C11 H11 120.2 . . ?
C10 C11 H11 120.2 . . ?
C11 C12 C13 119.8(3) . . ?
C11 C12 H12 120.1 . . ?
C13 C12 H12 120.1 . . ?
C14 C13 C12 120.4(3) . . ?
C14 C13 H13 119.8 . . ?
C12 C13 H13 119.8 . . ?
C13 C14 C15 120.2(3) . . ?
C13 C14 H14 119.9 . . ?
C15 C14 H14 119.9 . . ?
C10 C15 C14 119.3(3) . . ?
C10 C15 H15 120.4 . . ?
C14 C15 H15 120.4 . . ?
C17 C16 C21 120.6(2) . . ?
C17 C16 S1 119.22(18) . . ?
C21 C16 S1 120.17(18) . . ?
C16 C17 C18 119.4(2) . . ?
C16 C17 H17 120.3 . . ?
C18 C17 H17 120.3 . . ?
C17 C18 C19 121.4(2) . . ?
C17 C18 H18 119.3 . . ?
C19 C18 H18 119.3 . . ?
C18 C19 C20 118.1(2) . . ?
C18 C19 C22 120.7(2) . . ?
C20 C19 C22 121.1(2) . . ?
C21 C20 C19 121.5(2) . . ?
C21 C20 H20 119.3 . . ?
C19 C20 H20 119.3 . . ?
C20 C21 C16 119.0(2) . . ?
C20 C21 H21 120.5 . . ?
C16 C21 H21 120.5 . . ?
C19 C22 H22A 109.5 . . ?
C19 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C19 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C7 N1 N2 115.73(18) . . ?
N1 N2 C10 115.12(18) . . ?
N1 N2 S1 107.26(14) . . ?
C10 N2 S1 115.54(15) . . ?
C8 N3 C1 111.1(2) . . ?
C8 N3 C9 123.3(2) . . ?
C1 N3 C9 125.6(2) . . ?
O1 S1 O2 120.47(12) . . ?
O1 S1 N2 105.31(11) . . ?
O2 S1 N2 104.90(10) . . ?
O1 S1 C16 109.31(11) . . ?
O2 S1 C16 109.77(11) . . ?
N2 S1 C16 106.00(10) . . ?

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 C1 C2 C3 -0.9(4) . . . . ?
N3 C1 C2 C3 178.0(3) . . . . ?
C1 C2 C3 C4 -0.6(4) . . . . ?
C2 C3 C4 C5 0.8(5) . . . . ?
C3 C4 C5 C6 0.5(4) . . . . ?
C4 C5 C6 C1 -1.9(4) . . . . ?
C4 C5 C6 C7 -175.8(3) . . . . ?
C2 C1 C6 C5 2.2(4) . . . . ?
N3 C1 C6 C5 -176.9(2) . . . . ?
C2 C1 C6 C7 177.6(2) . . . . ?
N3 C1 C6 C7 -1.6(3) . . . . ?
C5 C6 C7 N1 -6.7(5) . . . . ?
C1 C6 C7 N1 178.8(3) . . . . ?
C5 C6 C7 C8 173.9(3) . . . . ?
C1 C6 C7 C8 -0.6(3) . . . . ?
N1 C7 C8 O3 0.3(4) . . . . ?
C6 C7 C8 O3 179.9(3) . . . . ?
N1 C7 C8 N3 -177.0(2) . . . . ?
C6 C7 C8 N3 2.5(3) . . . . ?
C15 C10 C11 C12 0.4(4) . . . . ?
N2 C10 C11 C12 -178.9(2) . . . . ?
C10 C11 C12 C13 -2.3(4) . . . . ?
C11 C12 C13 C14 2.7(4) . . . . ?
C12 C13 C14 C15 -1.2(4) . . . . ?
C11 C10 C15 C14 1.0(4) . . . . ?
N2 C10 C15 C14 -179.6(2) . . . . ?
C13 C14 C15 C10 -0.6(4) . . . . ?
C21 C16 C17 C18 -1.4(4) . . . . ?
S1 C16 C17 C18 176.21(19) . . . . ?
C16 C17 C18 C19 -0.7(4) . . . . ?
C17 C18 C19 C20 1.8(4) . . . . ?
C17 C18 C19 C22 -176.2(2) . . . . ?
C18 C19 C20 C21 -1.0(4) . . . . ?
C22 C19 C20 C21 177.1(2) . . . . ?
C19 C20 C21 C16 -1.0(4) . . . . ?
C17 C16 C21 C20 2.1(4) . . . . ?
S1 C16 C21 C20 -175.39(19) . . . . ?
C6 C7 N1 N2 -6.3(4) . . . . ?
C8 C7 N1 N2 172.97(19) . . . . ?
C7 N1 N2 C10 -69.5(2) . . . . ?
C7 N1 N2 S1 160.37(17) . . . . ?
C15 C10 N2 N1 151.8(2) . . . . ?
C11 C10 N2 N1 -28.8(3) . . . . ?
C15 C10 N2 S1 -82.2(2) . . . . ?
C11 C10 N2 S1 97.1(2) . . . . ?
O3 C8 N3 C1 179.1(3) . . . . ?
C7 C8 N3 C1 -3.5(3) . . . . ?
O3 C8 N3 C9 1.9(4) . . . . ?
C7 C8 N3 C9 179.4(2) . . . . ?
C2 C1 N3 C8 -175.7(3) . . . . ?
C6 C1 N3 C8 3.4(3) . . . . ?
C2 C1 N3 C9 1.4(4) . . . . ?
C6 C1 N3 C9 -179.6(3) . . . . ?
N1 N2 S1 O1 -59.66(16) . . . . ?
C10 N2 S1 O1 170.47(16) . . . . ?
N1 N2 S1 O2 172.26(14) . . . . ?
C10 N2 S1 O2 42.39(18) . . . . ?
N1 N2 S1 C16 56.13(16) . . . . ?
C10 N2 S1 C16 -73.74(17) . . . . ?
C17 C16 S1 O1 11.5(2) . . . . ?
C21 C16 S1 O1 -170.91(19) . . . . ?
C17 C16 S1 O2 145.69(19) . . . . ?
C21 C16 S1 O2 -36.7(2) . . . . ?
C17 C16 S1 N2 -101.5(2) . . . . ?
C21 C16 S1 N2 76.0(2) . . . . ?

_refine_diff_density_max         0.246
_refine_diff_density_min         -0.358
_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_SS2_91F1_140622_0m_a
_database_code_depnum_ccdc_archive 'CCDC 2179829'
loop_
_audit_author_name
_audit_author_address
'Snoxma Smile'
;CSIR CLRI
India
;
_audit_update_record             
;
2022-06-17 deposited with the CCDC.	2023-01-17 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        4,4'-sulfonylbis(methylbenzene)
_chemical_name_common            SS2-91F1
_chemical_melting_point          ?
_chemical_formula_moiety         'C13 H12 O2 S'
_chemical_formula_sum            'C13 H12 O2 S'
_chemical_formula_weight         232.29

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'
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                   13.0543(13)
_cell_length_b                   7.8336(8)
_cell_length_c                   11.5876(12)
_cell_angle_alpha                90
_cell_angle_beta                 95.968(3)
_cell_angle_gamma                90
_cell_volume                     1178.6(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    300(2)
_cell_measurement_reflns_used    8400
_cell_measurement_theta_min      3.04
_cell_measurement_theta_max      25.68

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.309
_exptl_crystal_F_000             488
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.180
_exptl_crystal_size_mid          0.140
_exptl_crystal_size_min          0.050
_exptl_absorpt_coefficient_mu    0.256
_shelx_estimated_absorpt_T_min   0.955
_shelx_estimated_absorpt_T_max   0.987
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6516
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_process_details   
;
 SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
 J. Appl. Cryst. 48 (2015) 3-10
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      300(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'i-mu-s microfocus source'
_diffrn_measurement_device_type  
'Bruker D8 QUEST diffractometer with PHOTON II detector'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            26064
_diffrn_reflns_av_unetI/netI     0.0320
_diffrn_reflns_av_R_equivalents  0.0500
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         3.037
_diffrn_reflns_theta_max         28.360
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             2939
_reflns_number_gt                1916
_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 APEX4'
_computing_cell_refinement       'Bruker APEX4/SAINT'
_computing_data_reduction        'Bruker APEX4/SAINT'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_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)+(0.0293P)²+0.7008P] 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     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2939
_refine_ls_number_parameters     146
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0918
_refine_ls_R_factor_gt           0.0524
_refine_ls_wR_factor_ref         0.1198
_refine_ls_wR_factor_gt          0.0991
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_restrained_S_all      1.039
_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
S2 S 0.27013(4) 0.33249(8) 0.68056(5) 0.0618(2) Uani 1 1 d . . . . .
O2 O 0.26997(14) 0.3924(3) 0.79781(14) 0.0882(6) Uani 1 1 d . . . . .
O3 O 0.22698(13) 0.1681(2) 0.6495(2) 0.0929(7) Uani 1 1 d . . . . .
C1 C 0.47206(17) 0.4222(3) 0.71525(19) 0.0569(6) Uani 1 1 d . . . . .
H1 H 0.453798 0.484503 0.778301 0.068 Uiso 1 1 calc R U . . .
C2 C 0.57291(18) 0.4185(3) 0.6904(2) 0.0663(6) Uani 1 1 d . . . . .
H2 H 0.623276 0.476849 0.737541 0.080 Uiso 1 1 calc R U . . .
C3 C 0.59901(18) 0.3292(3) 0.5966(2) 0.0640(6) Uani 1 1 d . . . . .
H3 H 0.667203 0.326811 0.580142 0.077 Uiso 1 1 calc R U . . .
C4 C 0.5255(2) 0.2432(3) 0.5269(2) 0.0683(7) Uani 1 1 d . . . . .
H4 H 0.543953 0.183851 0.462708 0.082 Uiso 1 1 calc R U . . .
C5 C 0.42445(18) 0.2435(3) 0.55074(19) 0.0604(6) Uani 1 1 d . . . . .
H5 H 0.374511 0.184377 0.503473 0.072 Uiso 1 1 calc R U . . .
C6 C 0.20643(15) 0.4849(3) 0.58732(18) 0.0490(5) Uani 1 1 d . . . . .
C7 C 0.15909(18) 0.4370(3) 0.4805(2) 0.0654(6) Uani 1 1 d . . . . .
H7 H 0.160793 0.323836 0.456540 0.078 Uiso 1 1 calc R U . . .
C8 C 0.10905(19) 0.5589(4) 0.4093(2) 0.0726(7) Uani 1 1 d . . . . .
H8 H 0.076744 0.526200 0.337422 0.087 Uiso 1 1 calc R U . . .
C9 C 0.10575(16) 0.7271(3) 0.4420(2) 0.0617(6) Uani 1 1 d . . . . .
C10 C 0.15569(18) 0.7731(3) 0.5483(2) 0.0651(6) Uani 1 1 d . . . . .
H10 H 0.155478 0.886798 0.571389 0.078 Uiso 1 1 calc R U . . .
C11 C 0.20576(17) 0.6536(3) 0.62077(19) 0.0587(6) Uani 1 1 d . . . . .
H11 H 0.239071 0.686718 0.692115 0.070 Uiso 1 1 calc R U . . .
C12 C 0.0487(2) 0.8585(4) 0.3647(3) 0.0944(10) Uani 1 1 d . . . . .
H12A H 0.086423 0.963863 0.369574 0.142 Uiso 1 1 calc R U . . .
H12B H -0.018391 0.876695 0.389515 0.142 Uiso 1 1 calc R U . . .
H12C H 0.041711 0.818489 0.286012 0.142 Uiso 1 1 calc R U . . .
C14 C 0.39851(15) 0.3330(2) 0.64603(17) 0.0450(5) 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
S2 O3 1.4361(19) . ?
S2 O2 1.4376(19) . ?
S2 C6 1.760(2) . ?
S2 C14 1.763(2) . ?
C1 C14 1.376(3) . ?
C1 C2 1.377(3) . ?
C2 C3 1.365(3) . ?
C3 C4 1.366(3) . ?
C4 C5 1.376(3) . ?
C5 C14 1.380(3) . ?
C6 C7 1.377(3) . ?
C6 C11 1.378(3) . ?
C7 C8 1.381(3) . ?
C8 C9 1.373(4) . ?
C9 C10 1.380(3) . ?
C9 C12 1.509(3) . ?
C10 C11 1.376(3) . ?

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
O3 S2 O2 119.36(13) . . ?
O3 S2 C6 107.84(11) . . ?
O2 S2 C6 108.16(11) . . ?
O3 S2 C14 107.62(11) . . ?
O2 S2 C14 107.98(10) . . ?
C6 S2 C14 105.00(9) . . ?
C14 C1 C2 119.5(2) . . ?
C3 C2 C1 120.0(2) . . ?
C2 C3 C4 120.4(2) . . ?
C3 C4 C5 120.7(2) . . ?
C4 C5 C14 118.8(2) . . ?
C7 C6 C11 119.9(2) . . ?
C7 C6 S2 120.43(18) . . ?
C11 C6 S2 119.64(17) . . ?
C6 C7 C8 119.3(2) . . ?
C9 C8 C7 121.7(2) . . ?
C8 C9 C10 118.1(2) . . ?
C8 C9 C12 121.3(3) . . ?
C10 C9 C12 120.6(3) . . ?
C11 C10 C9 121.1(2) . . ?
C10 C11 C6 119.8(2) . . ?
C1 C14 C5 120.7(2) . . ?
C1 C14 S2 119.41(16) . . ?
C5 C14 S2 119.91(16) . . ?

_refine_diff_density_max         0.260
_refine_diff_density_min         -0.299
_refine_diff_density_rms         0.038

####################################################################### 
# 
# 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_SS2_99F1_160622_0m_a
_database_code_depnum_ccdc_archive 'CCDC 2179832'
loop_
_audit_author_name
_audit_author_address
'Snoxma Smile'
;CSIR CLRI
India
;
_audit_update_record             
;
2022-06-17 deposited with the CCDC.	2023-01-17 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        4'-methoxyspiro[fluorene-9,3'-indazole]
_chemical_name_common            SS2-99F1
_chemical_melting_point          ?
_chemical_formula_moiety         'C20 H14 N2 O'
_chemical_formula_sum            'C20 H14 N2 O'
_chemical_formula_weight         298.33

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

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

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

_cell_length_a                   8.7215(4)
_cell_length_b                   8.0965(4)
_cell_length_c                   21.5872(11)
_cell_angle_alpha                90
_cell_angle_beta                 98.010(2)
_cell_angle_gamma                90
_cell_volume                     1509.48(13)
_cell_formula_units_Z            4
_cell_measurement_temperature    300(2)
_cell_measurement_reflns_used    6019
_cell_measurement_theta_min      2.69
_cell_measurement_theta_max      27.81

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.313
_exptl_crystal_F_000             624
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.230
_exptl_crystal_size_mid          0.190
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    0.082
_shelx_estimated_absorpt_T_min   0.981
_shelx_estimated_absorpt_T_max   0.992
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6965
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_process_details   'SADABS (Bruker)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      300(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'i-mu-s microfocus source'
_diffrn_measurement_device_type  
'Bruker D8 QUEST diffractometer with PHOTON II detector'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            19671
_diffrn_reflns_av_unetI/netI     0.0427
_diffrn_reflns_av_R_equivalents  0.0432
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_theta_min         1.905
_diffrn_reflns_theta_max         28.196
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measured_fraction_theta_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_point_group_measured_fraction_full 0.992
_reflns_number_total             3694
_reflns_number_gt                2342
_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 APEX4'
_computing_cell_refinement       'Bruker APEX4/SAINT'
_computing_data_reduction        'Bruker APEX4/SAINT'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_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)+(0.0585P)²+0.3359P] 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     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3694
_refine_ls_number_parameters     209
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0914
_refine_ls_R_factor_gt           0.0495
_refine_ls_wR_factor_ref         0.1405
_refine_ls_wR_factor_gt          0.1136
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_restrained_S_all      1.031
_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
O1 O 0.45954(13) 0.49932(13) 0.36249(6) 0.0536(3) Uani 1 1 d . . . . .
N1 N 0.65524(15) 0.99881(16) 0.39988(6) 0.0478(4) Uani 1 1 d . . . . .
N2 N 0.75385(16) 0.94521(18) 0.44315(7) 0.0519(4) Uani 1 1 d . . . . .
C1 C 0.61821(17) 0.71315(19) 0.40625(7) 0.0395(4) Uani 1 1 d . . . . .
C2 C 0.57753(18) 0.54790(19) 0.40609(7) 0.0424(4) Uani 1 1 d . . . . .
C3 C 0.6611(2) 0.4446(2) 0.45008(8) 0.0546(5) Uani 1 1 d . . . . .
H3 H 0.636939 0.332724 0.450527 0.066 Uiso 1 1 calc R U . . .
C4 C 0.7797(2) 0.5063(2) 0.49311(9) 0.0635(5) Uani 1 1 d . . . . .
H4 H 0.833300 0.434598 0.522074 0.076 Uiso 1 1 calc R U . . .
C5 C 0.8206(2) 0.6701(2) 0.49437(8) 0.0608(5) Uani 1 1 d . . . . .
H5 H 0.900311 0.711438 0.523336 0.073 Uiso 1 1 calc R U . . .
C6 C 0.73663(18) 0.7701(2) 0.45011(7) 0.0457(4) Uani 1 1 d . . . . .
C7 C 0.55520(17) 0.85754(18) 0.36848(7) 0.0401(4) Uani 1 1 d . . . . .
C8 C 0.4154(2) 0.3293(2) 0.36201(11) 0.0676(6) Uani 1 1 d . . . . .
H8A H 0.336543 0.308993 0.327157 0.101 Uiso 1 1 calc R U . . .
H8B H 0.376040 0.303257 0.400229 0.101 Uiso 1 1 calc R U . . .
H8C H 0.503879 0.261366 0.358322 0.101 Uiso 1 1 calc R U . . .
C9 C 0.57317(18) 0.87072(18) 0.29948(7) 0.0418(4) Uani 1 1 d . . . . .
C10 C 0.38610(17) 0.90346(18) 0.36767(7) 0.0397(4) Uani 1 1 d . . . . .
C11 C 0.32315(18) 0.95793(19) 0.30806(7) 0.0425(4) Uani 1 1 d . . . . .
C12 C 0.44122(18) 0.94345(19) 0.26636(7) 0.0433(4) Uani 1 1 d . . . . .
C13 C 0.4395(2) 0.9869(2) 0.20388(8) 0.0562(5) Uani 1 1 d . . . . .
H13 H 0.354025 1.039822 0.181948 0.067 Uiso 1 1 calc R U . . .
C14 C 0.5670(2) 0.9500(3) 0.17508(9) 0.0688(6) Uani 1 1 d . . . . .
H14 H 0.567264 0.978406 0.133355 0.083 Uiso 1 1 calc R U . . .
C15 C 0.6935(2) 0.8718(3) 0.20733(10) 0.0706(6) Uani 1 1 d . . . . .
H15 H 0.776352 0.843927 0.186525 0.085 Uiso 1 1 calc R U . . .
C16 C 0.7002(2) 0.8334(2) 0.27056(9) 0.0562(5) Uani 1 1 d . . . . .
H16 H 0.787556 0.784171 0.292578 0.067 Uiso 1 1 calc R U . . .
C17 C 0.2992(2) 0.9004(2) 0.41606(8) 0.0503(4) Uani 1 1 d . . . . .
H17 H 0.342177 0.864918 0.455660 0.060 Uiso 1 1 calc R U . . .
C18 C 0.1461(2) 0.9515(2) 0.40466(9) 0.0589(5) Uani 1 1 d . . . . .
H18 H 0.085386 0.949239 0.436833 0.071 Uiso 1 1 calc R U . . .
C19 C 0.0831(2) 1.0054(2) 0.34611(10) 0.0588(5) Uani 1 1 d . . . . .
H19 H -0.019773 1.039300 0.339308 0.071 Uiso 1 1 calc R U . . .
C20 C 0.1698(2) 1.0100(2) 0.29737(9) 0.0529(5) Uani 1 1 d . . . . .
H20 H 0.126512 1.047242 0.258052 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
O1 C2 1.3526(19) . ?
O1 C8 1.429(2) . ?
N1 N2 1.2556(18) . ?
N1 C7 1.5377(19) . ?
N2 C6 1.436(2) . ?
C1 C6 1.380(2) . ?
C1 C2 1.384(2) . ?
C1 C7 1.486(2) . ?
C2 C3 1.393(2) . ?
C3 C4 1.384(3) . ?
C4 C5 1.373(3) . ?
C5 C6 1.382(2) . ?
C7 C10 1.519(2) . ?
C7 C9 1.523(2) . ?
C9 C16 1.379(2) . ?
C9 C12 1.397(2) . ?
C10 C17 1.374(2) . ?
C10 C11 1.398(2) . ?
C11 C20 1.390(2) . ?
C11 C12 1.464(2) . ?
C12 C13 1.392(2) . ?
C13 C14 1.380(3) . ?
C14 C15 1.375(3) . ?
C15 C16 1.393(3) . ?
C17 C18 1.387(2) . ?
C18 C19 1.377(3) . ?
C19 C20 1.379(3) . ?

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 O1 C8 117.60(13) . . ?
N2 N1 C7 111.02(12) . . ?
N1 N2 C6 110.38(13) . . ?
C6 C1 C2 119.48(14) . . ?
C6 C1 C7 107.32(14) . . ?
C2 C1 C7 133.15(14) . . ?
O1 C2 C1 116.92(13) . . ?
O1 C2 C3 125.09(15) . . ?
C1 C2 C3 117.99(15) . . ?
C4 C3 C2 120.79(17) . . ?
C5 C4 C3 122.02(16) . . ?
C4 C5 C6 116.17(17) . . ?
C1 C6 C5 123.54(16) . . ?
C1 C6 N2 109.73(13) . . ?
C5 C6 N2 126.70(15) . . ?
C1 C7 C10 118.89(13) . . ?
C1 C7 C9 120.74(13) . . ?
C10 C7 C9 101.75(12) . . ?
C1 C7 N1 101.51(11) . . ?
C10 C7 N1 108.27(12) . . ?
C9 C7 N1 104.45(12) . . ?
C16 C9 C12 121.13(16) . . ?
C16 C9 C7 128.77(15) . . ?
C12 C9 C7 109.89(14) . . ?
C17 C10 C11 121.19(15) . . ?
C17 C10 C7 128.67(14) . . ?
C11 C10 C7 110.12(14) . . ?
C20 C11 C10 119.57(16) . . ?
C20 C11 C12 131.69(15) . . ?
C10 C11 C12 108.72(13) . . ?
C13 C12 C9 119.94(16) . . ?
C13 C12 C11 131.45(15) . . ?
C9 C12 C11 108.60(13) . . ?
C14 C13 C12 118.76(17) . . ?
C15 C14 C13 120.80(18) . . ?
C14 C15 C16 121.31(19) . . ?
C9 C16 C15 117.94(18) . . ?
C10 C17 C18 118.67(16) . . ?
C19 C18 C17 120.55(18) . . ?
C18 C19 C20 121.18(17) . . ?
C19 C20 C11 118.84(17) . . ?

_refine_diff_density_max         0.163
_refine_diff_density_min         -0.159
_refine_diff_density_rms         0.037

####################################################################### 
# 
# 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_SS2_88F2_150622_0m_a
_database_code_depnum_ccdc_archive 'CCDC 2179825'
loop_
_audit_author_name
_audit_author_address
'Snoxma Smile'
;CSIR CLRI
India
;
_audit_update_record             
;
2022-06-17 deposited with the CCDC.	2023-01-17 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C15 H10 Br N3 O'
_chemical_formula_sum            'C15 H10 Br N3 O'
_chemical_formula_weight         328.17

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'
Br Br -0.2901 2.4595 '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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

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

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

_cell_length_a                   12.2098(8)
_cell_length_b                   8.7386(6)
_cell_length_c                   13.4142(9)
_cell_angle_alpha                90
_cell_angle_beta                 108.433(2)
_cell_angle_gamma                90
_cell_volume                     1357.82(16)
_cell_formula_units_Z            4
_cell_measurement_temperature    300(2)
_cell_measurement_reflns_used    7169
_cell_measurement_theta_min      2.73
_cell_measurement_theta_max      26.95

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.605
_exptl_crystal_F_000             656
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.150
_exptl_crystal_size_mid          0.110
_exptl_crystal_size_min          0.070
_exptl_absorpt_coefficient_mu    3.025
_shelx_estimated_absorpt_T_min   0.660
_shelx_estimated_absorpt_T_max   0.816
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6233
_exptl_absorpt_correction_T_max  0.7455
_exptl_absorpt_process_details   SADABS(Bruker)
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      300(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'i-mu-s microfocus source'
_diffrn_measurement_device_type  
'Bruker D8 diffractometer with PHOTON II detector'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            23806
_diffrn_reflns_av_unetI/netI     0.0414
_diffrn_reflns_av_R_equivalents  0.0518
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         1.968
_diffrn_reflns_theta_max         27.121
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             2977
_reflns_number_gt                2025
_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 APEX4'
_computing_cell_refinement       'Bruker APEX4/SAINT'
_computing_data_reduction        'Bruker APEX4/SAINT'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_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)+(0.0591P)²+0.4927P] 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     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2977
_refine_ls_number_parameters     182
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0810
_refine_ls_R_factor_gt           0.0453
_refine_ls_wR_factor_ref         0.1172
_refine_ls_wR_factor_gt          0.1039
_refine_ls_goodness_of_fit_ref   1.021
_refine_ls_restrained_S_all      1.021
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 0.71105(3) 0.51711(4) 0.41938(3) 0.06601(19) Uani 1 1 d . . . . .
O1 O 0.6294(2) 0.2080(3) 0.1790(2) 0.0694(7) Uani 1 1 d . . . . .
N1 N 0.3833(2) 0.2922(3) 0.1584(2) 0.0547(7) Uani 1 1 d . . . . .
N2 N 0.3503(2) 0.2141(3) 0.2224(2) 0.0568(7) Uani 1 1 d . . . . .
N3 N 0.6232(2) 0.4610(3) 0.1321(2) 0.0515(7) Uani 1 1 d . . . . .
C1 C 0.5107(2) 0.3401(3) 0.3273(2) 0.0411(7) Uani 1 1 d . . . . .
C2 C 0.4244(3) 0.2369(3) 0.3271(2) 0.0484(8) Uani 1 1 d . . . . .
C3 C 0.4163(3) 0.1734(4) 0.4183(3) 0.0649(10) Uani 1 1 d . . . . .
H3 H 0.357589 0.105194 0.417649 0.078 Uiso 1 1 calc R U . . .
C4 C 0.4993(3) 0.2153(6) 0.5109(3) 0.0712(12) Uani 1 1 d . . . . .
H4 H 0.495845 0.175109 0.574006 0.085 Uiso 1 1 calc R U . . .
C5 C 0.5878(3) 0.3159(4) 0.5121(3) 0.0626(9) Uani 1 1 d . . . . .
H5 H 0.643806 0.340419 0.575238 0.075 Uiso 1 1 calc R U . . .
C6 C 0.5923(3) 0.3793(3) 0.4196(2) 0.0464(7) Uani 1 1 d . . . . .
C7 C 0.4899(2) 0.3838(4) 0.2155(2) 0.0436(7) Uani 1 1 d . . . . .
C8 C 0.4760(3) 0.5508(4) 0.1872(2) 0.0428(7) Uani 1 1 d . . . . .
C9 C 0.5901(3) 0.3347(4) 0.1738(2) 0.0487(8) Uani 1 1 d . . . . .
C10 C 0.5568(3) 0.5904(4) 0.1397(2) 0.0477(8) Uani 1 1 d . . . . .
C11 C 0.5662(3) 0.7381(4) 0.1079(3) 0.0643(10) Uani 1 1 d . . . . .
H11 H 0.620221 0.764480 0.075131 0.077 Uiso 1 1 calc R U . . .
C12 C 0.4918(4) 0.8459(4) 0.1265(3) 0.0787(12) Uani 1 1 d . . . . .
H12 H 0.496551 0.946955 0.106479 0.094 Uiso 1 1 calc R U . . .
C13 C 0.4116(4) 0.8071(4) 0.1737(3) 0.0704(11) Uani 1 1 d . . . . .
H13 H 0.362538 0.881735 0.184944 0.085 Uiso 1 1 calc R U . . .
C14 C 0.4026(3) 0.6586(4) 0.2048(3) 0.0568(9) Uani 1 1 d . . . . .
H14 H 0.348080 0.632202 0.236995 0.068 Uiso 1 1 calc R U . . .
C15 C 0.7229(4) 0.4646(5) 0.0961(3) 0.0736(11) Uani 1 1 d . . . . .
H15A H 0.699298 0.492566 0.023139 0.110 Uiso 1 1 calc R U . . .
H15B H 0.758262 0.365286 0.104842 0.110 Uiso 1 1 calc R U . . .
H15C H 0.777332 0.538360 0.136302 0.110 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 C6 1.886(3) . ?
O1 C9 1.199(4) . ?
N1 N2 1.259(3) . ?
N1 C7 1.513(4) . ?
N2 C2 1.423(4) . ?
N3 C9 1.356(4) . ?
N3 C10 1.413(4) . ?
N3 C15 1.445(4) . ?
C1 C6 1.365(4) . ?
C1 C2 1.387(4) . ?
C1 C7 1.489(4) . ?
C2 C3 1.375(4) . ?
C3 C4 1.381(5) . ?
C4 C5 1.389(5) . ?
C5 C6 1.376(4) . ?
C7 C8 1.504(4) . ?
C7 C9 1.558(4) . ?
C8 C14 1.371(4) . ?
C8 C10 1.378(4) . ?
C10 C11 1.375(5) . ?
C11 C12 1.385(6) . ?
C12 C13 1.366(6) . ?
C13 C14 1.378(5) . ?

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
N2 N1 C7 110.5(2) . . ?
N1 N2 C2 110.9(2) . . ?
C9 N3 C10 111.7(3) . . ?
C9 N3 C15 123.2(3) . . ?
C10 N3 C15 124.7(3) . . ?
C6 C1 C2 120.1(3) . . ?
C6 C1 C7 133.8(3) . . ?
C2 C1 C7 106.1(3) . . ?
C3 C2 C1 121.9(3) . . ?
C3 C2 N2 128.3(3) . . ?
C1 C2 N2 109.8(3) . . ?
C2 C3 C4 117.0(3) . . ?
C3 C4 C5 121.7(3) . . ?
C6 C5 C4 119.8(3) . . ?
C1 C6 C5 119.4(3) . . ?
C1 C6 Br1 120.0(2) . . ?
C5 C6 Br1 120.6(3) . . ?
C1 C7 C8 118.2(2) . . ?
C1 C7 N1 102.7(2) . . ?
C8 C7 N1 112.1(2) . . ?
C1 C7 C9 112.8(3) . . ?
C8 C7 C9 102.4(2) . . ?
N1 C7 C9 108.6(2) . . ?
C14 C8 C10 120.7(3) . . ?
C14 C8 C7 130.6(3) . . ?
C10 C8 C7 108.7(3) . . ?
O1 C9 N3 127.6(3) . . ?
O1 C9 C7 125.3(3) . . ?
N3 C9 C7 107.1(3) . . ?
C11 C10 C8 121.4(3) . . ?
C11 C10 N3 128.5(3) . . ?
C8 C10 N3 110.1(3) . . ?
C10 C11 C12 117.3(4) . . ?
C13 C12 C11 121.4(4) . . ?
C12 C13 C14 120.8(4) . . ?
C8 C14 C13 118.4(3) . . ?

_refine_diff_density_max         0.651
_refine_diff_density_min         -0.441
_refine_diff_density_rms         0.071

