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_7160746
_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 N3 O6'
_chemical_formula_sum            'C24 H17 N3 O6'
_chemical_formula_weight         443.40
_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
_atom_sites_solution_primary     dual
_audit_creation_date             2025-06-04
_audit_creation_method
;
Olex2 1.5-ac6-016
(compiled 2024.01.13 svn.r2f8d729c for Rigaku Oxford Diffraction, GUI svn.r6897)
;
_audit_update_record
;
2025-06-04 deposited with the CCDC.	2025-09-22 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90.591(5)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.3383(7)
_cell_length_b                   12.3765(9)
_cell_length_c                   14.6007(8)
_cell_measurement_reflns_used    2032
_cell_measurement_temperature    106(8)
_cell_measurement_theta_max      24.7690
_cell_measurement_theta_min      2.1380
_cell_volume                     2048.8(2)
_computing_cell_refinement       'CrysAlisPro 1.171.43.105a (Rigaku OD, 2024)'
_computing_data_collection
'PROGRAM:BIS V6.2.16/2021-10-22 && APEX4 2021.4-0                                '
_computing_data_reduction        'CrysAlisPro 1.171.43.105a (Rigaku OD, 2024)'
_computing_molecular_graphics    'Olex2 1.5-ac6-016 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-ac6-016 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      106(8)
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 0.983
_diffrn_measured_fraction_theta_max 0.983
_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   -108.63  15.87   0.50    2.00    --  -12.98 -59.25  71.08  249
  2  \f    -78.01  65.99   0.50    2.00   9.42 -12.98 -31.50    --   288
  3  \f    -68.21  75.79   0.50    2.00  16.12 -12.98 -59.25    --   288
;
_diffrn_measurement_device       'abstract diffractometer'
_diffrn_measurement_device_type
'Saxi-CrysAlisPro-abstract goniometer imported SAXI images'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0556326000
_diffrn_orient_matrix_UB_12      0.0111052000
_diffrn_orient_matrix_UB_13      0.0195987000
_diffrn_orient_matrix_UB_21      -0.0274418000
_diffrn_orient_matrix_UB_22      -0.0069015000
_diffrn_orient_matrix_UB_23      -0.0434895000
_diffrn_orient_matrix_UB_31      -0.0078439000
_diffrn_orient_matrix_UB_32      -0.0558194000
_diffrn_orient_matrix_UB_33      0.0092606000
_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  0.1641
_diffrn_reflns_av_unetI/netI     0.0961
_diffrn_reflns_Laue_measured_fraction_full 0.983
_diffrn_reflns_Laue_measured_fraction_max 0.983
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            21376
_diffrn_reflns_point_group_measured_fraction_full 0.983
_diffrn_reflns_point_group_measured_fraction_max 0.983
_diffrn_reflns_theta_full        24.992
_diffrn_reflns_theta_max         24.992
_diffrn_reflns_theta_min         2.157
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.106
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.05483
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.43.105a (Rigaku Oxford Diffraction, 2024)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.438
_exptl_crystal_description       block
_exptl_crystal_F_000             920
_exptl_crystal_size_max          0.17
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.13
_refine_diff_density_max         0.288
_refine_diff_density_min         -0.384
_refine_diff_density_rms         0.074
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     299
_refine_ls_number_reflns         3544
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.046
_refine_ls_R_factor_all          0.1063
_refine_ls_R_factor_gt           0.0674
_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^)+(0.0918P)^2^+0.0834P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1664
_refine_ls_wR_factor_ref         0.2006
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2272
_reflns_number_total             3544
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5ob01255d2.cif
_cod_data_source_block           inn_as_iv_117_new_autored
_cod_depositor_comments
'Adding full bibliography for 7160743--7160746.cif.'
_cod_database_code               7160746
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.986
_shelx_estimated_absorpt_t_min   0.982
_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:
 C00N(H00N)
2.b Secondary CH2 refined with riding coordinates:
 C00Q(H00A,H00B)
2.c Aromatic/amide H refined with riding coordinates:
 C00I(H00I), C00L(H00L), C00O(H00O), C00P(H00P), C00R(H00R), C00S(H00S),
 C00T(H00T), C00V(H00V), C00W(H00W)
2.d X=CH2 refined with riding coordinates:
 C1(H1A,H1B)
2.e Idealised Me refined as rotating group:
 C00U(H00C,H00D,H00E)
;
_shelx_res_checksum              66101
_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
;
_oxdiff_exptl_absorpt_empirical_full_max 5.855
_oxdiff_exptl_absorpt_empirical_full_min 0.271