#------------------------------------------------------------------------------
#$Date: 2023-03-04 20:29:42 +0200 (Sat, 04 Mar 2023) $
#$Revision: 281500 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/06/22/7062229.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_7062229
loop_
_publ_author_name
'Smile, Suresh Snoxma'
'Shanmugam, Ponnusamy'
_publ_section_title
;
 N--S bond cleavage of tosyl hydrazones by dual reactive arynes: synthesis
 of diaryl sulfones, spiro[indazole-3,3′-indolin]-2′-one,
 and N-phenyl sulfonohydrazides
;
_journal_issue                   8
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              3856
_journal_page_last               3863
_journal_paper_doi               10.1039/D3NJ00050H
_journal_volume                  47
_journal_year                    2023
_chemical_formula_moiety         'C22 H19 N3 O3 S'
_chemical_formula_sum            'C22 H19 N3 O3 S'
_chemical_formula_weight         405.46
_chemical_name_common            SS2-89F3
_chemical_name_systematic
(E)-4-methyl-N'-(1-methyl-2-oxoindolin-3-ylidene)-N-phenylbenzenesulfonohydrazide
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2022-06-16 deposited with the CCDC.	2023-01-17 downloaded from the CCDC.
;
_cell_angle_alpha                103.303(2)
_cell_angle_beta                 99.290(2)
_cell_angle_gamma                112.822(2)
_cell_formula_units_Z            2
_cell_length_a                   9.1555(6)
_cell_length_b                   10.4074(7)
_cell_length_c                   11.9079(7)
_cell_measurement_reflns_used    5468
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      26.40
_cell_measurement_theta_min      3.11
_cell_volume                     977.20(11)
_computing_cell_refinement       'APEX3/SAINT (Bruker, 2016)'
_computing_data_collection       'APEX3 (Bruker, 2016)'
_computing_data_reduction        'SAINT/XPREP (Bruker, 2016)'
_computing_molecular_graphics    'ORTEP3 (Farrugia, 1997) '
_computing_publication_material  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT-2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type
'Bruker D8 VENTURE diffractometer with PHOTON II detector'
_diffrn_measurement_method       'ω and φ scan'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1050
_diffrn_reflns_av_unetI/netI     0.0557
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            30992
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.484
_diffrn_reflns_theta_min         3.128
_exptl_absorpt_coefficient_mu    0.195
_exptl_absorpt_correction_T_max  0.986
_exptl_absorpt_correction_T_min  0.943
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Bruker, 2016)'
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.378
_exptl_crystal_description       block
_exptl_crystal_F_000             424
_exptl_crystal_size_max          0.238
_exptl_crystal_size_mid          0.117
_exptl_crystal_size_min          0.052
_refine_diff_density_max         0.246
_refine_diff_density_min         -0.358
_refine_diff_density_rms         0.048
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     264
_refine_ls_number_reflns         4015
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.027
_refine_ls_R_factor_all          0.0846
_refine_ls_R_factor_gt           0.0511
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0470P)²+0.3956P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1096
_refine_ls_wR_factor_ref         0.1251
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2773
_reflns_number_total             4015
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d3nj00050h2.cif
_cod_data_source_block           shelx
_cod_depositor_comments
'Adding full bibliography for 7062229--7062232.cif.'
_cod_database_code               7062229
_shelx_shelxl_version_number     2018/3
_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.
;
_shelx_estimated_absorpt_t_min   0.955
_shelx_estimated_absorpt_t_max   0.990
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'
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 . . . . .
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'
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_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_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) . . . . ?
