#------------------------------------------------------------------------------
#$Date: 2023-03-04 20:29:42 +0200 (Sat, 04 Mar 2023) $
#$Revision: 281500 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/06/22/7062231.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_7062231
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         'C20 H14 N2 O'
_chemical_formula_sum            'C20 H14 N2 O'
_chemical_formula_weight         298.33
_chemical_name_common            SS2-99F1
_chemical_name_systematic        4'-methoxyspiro[fluorene-9,3'-indazole]
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2022-06-17 deposited with the CCDC.	2023-01-17 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 98.010(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.7215(4)
_cell_length_b                   8.0965(4)
_cell_length_c                   21.5872(11)
_cell_measurement_reflns_used    6019
_cell_measurement_temperature    300(2)
_cell_measurement_theta_max      27.81
_cell_measurement_theta_min      2.69
_cell_volume                     1509.48(13)
_computing_cell_refinement       'Bruker APEX4/SAINT'
_computing_data_collection       'Bruker APEX4'
_computing_data_reduction        'Bruker APEX4/SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      300(2)
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type
'Bruker D8 QUEST diffractometer with PHOTON II detector'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0432
_diffrn_reflns_av_unetI/netI     0.0427
_diffrn_reflns_Laue_measured_fraction_full 0.992
_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       8
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            19671
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.196
_diffrn_reflns_theta_min         1.905
_diffrn_source                   'i-mu-s microfocus source'
_exptl_absorpt_coefficient_mu    0.082
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.6965
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Bruker)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.313
_exptl_crystal_description       block
_exptl_crystal_F_000             624
_exptl_crystal_size_max          0.230
_exptl_crystal_size_mid          0.190
_exptl_crystal_size_min          0.100
_refine_diff_density_max         0.163
_refine_diff_density_min         -0.159
_refine_diff_density_rms         0.037
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     209
_refine_ls_number_reflns         3694
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.031
_refine_ls_R_factor_all          0.0914
_refine_ls_R_factor_gt           0.0495
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0585P)²+0.3359P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1136
_refine_ls_wR_factor_ref         0.1405
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2342
_reflns_number_total             3694
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d3nj00050h2.cif
_cod_data_source_block           SS2_99F1_160622_0m_a
_cod_depositor_comments
'Adding full bibliography for 7062229--7062232.cif.'
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               7062231
_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   0.981
_shelx_estimated_absorpt_t_max   0.992
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'
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 . . .
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'
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) . . ?
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) . ?
