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_7160744
_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         'C37 H31 N3 O8 S'
_chemical_formula_sum            'C37 H31 N3 O8 S'
_chemical_formula_weight         677.71
_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_date             2025-09-01
_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                71.502(4)
_cell_angle_beta                 85.270(4)
_cell_angle_gamma                74.303(4)
_cell_formula_units_Z            2
_cell_length_a                   8.9817(4)
_cell_length_b                   13.1530(5)
_cell_length_c                   14.9506(6)
_cell_measurement_reflns_used    8704
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      30.2860
_cell_measurement_theta_min      2.3590
_cell_volume                     1612.48(12)
_computing_cell_refinement       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_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    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 28.5714
_diffrn_detector_type            'Rigaku Saturn724+'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_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  70.00   0.50   10.00    --  -20.00   0.00 108.00  360
  2  \w    -67.50  19.00   0.50   10.00    --  -20.00 -72.00-108.00  173
  3  \w    -76.50  10.00   0.50   10.00    --  -20.00 -72.00 108.00  173
  4  \w    -42.50  -3.00   0.50   10.00    --  -20.00  72.00  36.00   79
  5  \w    -59.00 -27.50   0.50   10.00    --  -20.00  72.00-108.00   63
  6  \w    -41.00 -10.50   0.50   10.00    --  -20.00 -72.00  36.00   61
  7  \w   -110.00  70.00   0.50   10.00    --  -20.00   0.00-180.00  360
  8  \w    -64.50  19.00   0.50   10.00    --  -20.00 -72.00 -36.00  167
  9  \w    -85.50   5.00   0.50   10.00    --  -20.00 -72.00-180.00  181
 10  \w    -42.50  -8.00   0.50   10.00    --  -20.00  72.00 108.00   69
 11  \w    -59.00 -52.50   0.50   10.00    --  -20.00  72.00 -36.00   13
;
_diffrn_measurement_device       'abstract diffractometer'
_diffrn_measurement_device_type
'dtrek-CrysAlisPro-abstract goniometer imported rigaku-d*trek images'
_diffrn_measurement_method       '\w scans'
_diffrn_measurement_specimen_support 'Mitegen 50um'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0902
_diffrn_reflns_av_unetI/netI     0.0735
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            26165
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        24.999
_diffrn_reflns_theta_max         24.999
_diffrn_reflns_theta_min         2.355
_exptl_absorpt_coefficient_mu    0.161
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.90789
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.43 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.396
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             708
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.114
_exptl_crystal_size_min          0.053
_refine_diff_density_max         0.311
_refine_diff_density_min         -0.506
_refine_diff_density_rms         0.077
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.071
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     445
_refine_ls_number_reflns         5678
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.071
_refine_ls_R_factor_all          0.0836
_refine_ls_R_factor_gt           0.0554
_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^)+(0.0462P)^2^+0.6606P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1132
_refine_ls_wR_factor_ref         0.1357
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4061
_reflns_number_total             5678
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5ob01255d2.cif
_cod_data_source_block           inn-as-iii-151_mo
_cod_depositor_comments
'Adding full bibliography for 7160743--7160746.cif.'
_cod_database_code               7160744
_shelx_shelxl_version_number     2018/3
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C16(H16), C18(H18)
2.b Secondary CH2 refined with riding coordinates:
 C17(H17A,H17B), C28(H28A,H28B)
2.c Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C6(H6), C7(H7), C10(H10), C11(H11), C12(H12), C13(H13),
 C22(H22), C23(H23), C24(H24), C25(H25), C32(H32), C33(H33), C34(H34), C35(H35)
2.d Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C), C29(H29A,H29B,H29C), C37(H37A,H37B,H37C)
;
_shelx_res_checksum              9651
_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
;