Synthesis of benzofuranyl indolinones and benzonaphthoxazepinones <i>via</i> reaction of sulfonyl phthalide with nitroisatylidenes.
Suresh, Alati; Satham, Lakshminarayana; Kumari, Rajni; Namboothiri, Irishi N. N.; Organic & biomolecular chemistry 23 (2025) 10300–10310; doi:10.1039/d5ob01255d

data_7160745
_publ_section_title
;
 Synthesis of benzofuranyl indolinones and benzonaphthoxazepinones
 <i>via</i> reaction of sulfonyl phthalide with nitroisatylidenes.
;
_journal_issue                   45
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              10300
_journal_page_last               10310
_journal_paper_doi               10.1039/d5ob01255d
_journal_volume                  23
_journal_year                    2025
_chemical_formula_moiety         'C24 H17 N O5 S'
_chemical_formula_sum            'C24 H17 N O5 S'
_chemical_formula_weight         431.44
_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
_atom_sites_solution_primary     dual
_audit_creation_date             2025-08-30
_audit_creation_method
;
Olex2 1.3-ac4
(compiled 2019.04.23 svn.r3594 for Rigaku Oxford Diffraction, GUI svn.r5739)
;
_audit_update_record
;
2025-09-01 deposited with the CCDC.	2025-09-22 downloaded from the CCDC.
;
_cell_angle_alpha                90.049(2)
_cell_angle_beta                 106.097(2)
_cell_angle_gamma                93.011(2)
_cell_formula_units_Z            2
_cell_length_a                   8.2207(2)
_cell_length_b                   9.1875(3)
_cell_length_c                   13.4343(4)
_cell_measurement_reflns_used    5698
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      31.1550
_cell_measurement_theta_min      2.5710
_cell_volume                     973.41(5)
_computing_cell_refinement       'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXD (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 0.974
_diffrn_measured_fraction_theta_max 0.842
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
  1  \w   -110.00  39.00   0.50    6.00    --  -20.00   0.00  36.00  298
  2  \w    -92.50  19.00   0.50    6.00    --  -20.00 -72.00  36.00  223
  3  \w    -69.00  -1.00   0.50    6.00    --  -20.00 -72.00-180.00  136
;
_diffrn_measurement_device       'abstract diffractometer'
_diffrn_measurement_device_type
'dtrek-CrysAlisPro-abstract goniometer imported rigaku-d*trek images'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0860505000
_diffrn_orient_matrix_UB_12      0.0019121000
_diffrn_orient_matrix_UB_13      -0.0006848000
_diffrn_orient_matrix_UB_21      -0.0260353000
_diffrn_orient_matrix_UB_22      -0.0008420000
_diffrn_orient_matrix_UB_23      -0.0549542000
_diffrn_orient_matrix_UB_31      0.0025282000
_diffrn_orient_matrix_UB_32      0.0772909000
_diffrn_orient_matrix_UB_33      0.0003014000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0356
_diffrn_reflns_av_unetI/netI     0.0490
_diffrn_reflns_Laue_measured_fraction_full 0.974
_diffrn_reflns_Laue_measured_fraction_max 0.842
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            8509
_diffrn_reflns_point_group_measured_fraction_full 0.974
_diffrn_reflns_point_group_measured_fraction_max 0.842
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         31.087
_diffrn_reflns_theta_min         2.583
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.206
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.94424
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.93a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'light colourless'
_exptl_crystal_density_diffrn    1.472
_exptl_crystal_description       block
_exptl_crystal_F_000             448
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.382
_refine_diff_density_min         -0.445
_refine_diff_density_rms         0.083
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     281
_refine_ls_number_reflns         5280
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.051
_refine_ls_R_factor_all          0.0539
_refine_ls_R_factor_gt           0.0434
_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/[\s^2^(Fo^2^)+(0.0570P)^2^+0.3328P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1100
_refine_ls_wR_factor_ref         0.1175
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4514
_reflns_number_total             5280
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5ob01255d2.cif
_cod_data_source_block           inn-as-iv-19_mo_autored
_cod_depositor_comments
'Adding full bibliography for 7160743--7160746.cif.'
_cod_database_code               7160745
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         CHONS
_reflns_odcompleteness_completeness 84.38
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     31.02
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C011(H011), C017(H017), C018(H018), C019(H019), C020(H020), C021(H021),
 C022(H022), C024(H024), C025(H025), C026(H026), C027(H027), C029(H029),
 C030(H030), C031(H031)
2.b Idealised Me refined as rotating group:
 C028(H02A,H02B,H02C)
;
_shelx_res_checksum              1668
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.188
_oxdiff_exptl_absorpt_empirical_full_min 0.829