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_7160743
_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         'C21 H13 N3 O6, H2 O, C4 H8 O2'
_chemical_formula_sum            'C25 H23 N3 O9'
_chemical_formula_weight         509.46
_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   mixed
_atom_sites_solution_primary     iterative
_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                99.228(3)
_cell_angle_beta                 91.601(3)
_cell_angle_gamma                92.646(3)
_cell_formula_units_Z            4
_cell_length_a                   9.4423(3)
_cell_length_b                   11.5086(4)
_cell_length_c                   21.8343(7)
_cell_measurement_reflns_used    9320
_cell_measurement_temperature    150
_cell_measurement_theta_max      31.0610
_cell_measurement_theta_min      2.1780
_cell_volume                     2337.97(13)
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_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    'olex2.solve (Bourhis et al., 2015)'
_diffrn_ambient_temperature      150.0
_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    8.00    --  -20.00   0.00 108.00  360
  2  \w    -65.50  19.00   0.50    8.00    --  -20.00 -72.00-108.00  169
  3  \w    -69.00   4.00   0.50    8.00    --  -20.00 -72.00 108.00  146
  4  \w    -68.50 -12.50   0.50    8.00    --  -20.00 -72.00  36.00  112
  5  \w    -59.00 -28.50   0.50    8.00    --  -20.00  72.00-108.00   61
  6  \w     -9.00  21.50   0.50    8.00    --  -20.00  72.00 -36.00   61
  7  \w   -110.00 -64.50   0.50    8.00    --  -20.00   0.00  36.00   91
;
_diffrn_measurement_device       'abstract diffractometer'
_diffrn_measurement_device_type
'dtrek-CrysAlisPro-abstract goniometer imported rigaku-d*trek images'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0515
_diffrn_reflns_av_unetI/netI     0.0597
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_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       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            22320
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         25.000
_diffrn_reflns_theta_min         1.889
_exptl_absorpt_coefficient_mu    0.112
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.94074
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
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    1.447
_exptl_crystal_description       block
_exptl_crystal_F_000             1064
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.293
_refine_diff_density_min         -0.307
_refine_diff_density_rms         0.066
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     681
_refine_ls_number_reflns         8225
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.036
_refine_ls_R_factor_all          0.0876
_refine_ls_R_factor_gt           0.0521
_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^)+(0.0586P)^2^+0.5949P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1185
_refine_ls_wR_factor_ref         0.1476
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5474
_reflns_number_total             8225
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5ob01255d2.cif
_cod_data_source_block           inn-as-iv-95_mo
_cod_depositor_comments
'Adding full bibliography for 7160743--7160746.cif.'
_cod_database_code               7160743
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.996
_shelx_estimated_absorpt_t_min   0.980
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups, All O(H,H) groups
2.a Free rotating group:
 O007(H00A,H00B), O00C(H00C,H00D)
2.b Secondary CH2 refined with riding coordinates:
 C01Y(H01N,H01P), C021(H02G,H02H)
2.c Aromatic/amide H refined with riding coordinates:
 N00G(H00G), N00J(H00J), C00U(H00U), C00W(H00W), C00Y(H00Y), C00Z(H00Z),
 C017(H017), C01A(H01A), C01B(H01B), C01E(H01F), C01I(H01I), C01J(H01J),
 C01K(H01K), C01L(H01L), C01O(H01O), C01Q(H01Q), C01R(H01R), C01U(H01U)
2.d Idealised Me refined as rotating group:
 C01S(H01W,H01X,H01Y), C01W(H01G,H01H,H01M), C01X(H01C,H01D,H01E), C01Z(H01S,
 H01T,H01V), C020(H02D,H02E,H02F), C022(H02A,H02B,H02C)
2.e Idealised tetrahedral OH refined as rotating group:
 O003(H003), O004(H004)
;
_shelx_res_checksum              88989
_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
;