Asymmetric C-H hydroarylation and annulation cascade for the skeletal diversification of dihydrofuran-fused-phthalimides.
Naskar, Paushali; Sau, Somratan; Sahoo, Akhila K.; Chemical communications (Cambridge, England) 61 (2025) 16098–16101; doi:10.1039/d5cc03717d

data_1575693
_publ_section_title
;
 Asymmetric C-H hydroarylation and annulation cascade for the skeletal
 diversification of dihydrofuran-fused-phthalimides.
;
_journal_issue                   82
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              16098
_journal_page_last               16101
_journal_paper_doi               10.1039/d5cc03717d
_journal_volume                  61
_journal_year                    2025
_chemical_absolute_configuration syn
_chemical_formula_moiety         'C18 H15 N O5 S'
_chemical_formula_sum            'C18 H15 N O5 S'
_chemical_formula_weight         357.37
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2023-03-14
_audit_creation_method
;
Olex2 1.3-ac4
(compiled 2018.12.18 svn.r3554 for Rigaku Oxford Diffraction, GUI svn.r1)
;
_audit_update_record
;
2025-05-25 deposited with the CCDC.	2025-09-11 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   5.13980(10)
_cell_length_b                   9.2922(2)
_cell_length_c                   34.4165(9)
_cell_measurement_reflns_used    6512
_cell_measurement_temperature    299.06
_cell_measurement_theta_max      25.3140
_cell_measurement_theta_min      2.2700
_cell_volume                     1643.73(6)
_computing_cell_refinement       'CrysAlisPro 1.171.40.35a (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.40.35a (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.40.35a (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    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      299.06
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix3000
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.974
_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      6.00  32.22   0.38    4.00    --   16.22  45.00 -30.00   69
  2  \w     44.00  70.22   0.38    4.00    --   16.22  45.00 -30.00   69
  3  \w     36.00  82.36   0.38    4.00    --   16.22  45.00-120.00  122
  4  \w     -7.00  32.14   0.38    4.00    --   16.22  45.00-120.00  103
  5  \w    -63.00  74.18   0.38    4.00    --   16.22 -15.00-112.00  361
  6  \w    -56.00  40.14   0.38    4.00    --   16.22 -30.00-120.00  253
  7  \w     16.00  76.80   0.38    4.00    --   16.22-136.00-144.00  160
  8  \w    -56.00 -14.96   0.38    4.00    --  -14.97 112.00-156.00  108
  9  \w    -69.00 -10.86   0.38    4.00    --  -14.97 125.00  90.00  153
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type
'XtaLAB Synergy, Single source at offset/far, HyPix3000'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0240624000
_diffrn_orient_matrix_UB_12      0.0689606000
_diffrn_orient_matrix_UB_13      0.0080735000
_diffrn_orient_matrix_UB_21      0.0124452000
_diffrn_orient_matrix_UB_22      -0.0291422000
_diffrn_orient_matrix_UB_23      0.0189664000
_diffrn_orient_matrix_UB_31      0.1352690000
_diffrn_orient_matrix_UB_32      0.0149116000
_diffrn_orient_matrix_UB_33      -0.0002979000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0227
_diffrn_reflns_av_unetI/netI     0.0300
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.974
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       41
_diffrn_reflns_limit_l_min       -42
_diffrn_reflns_number            11884
_diffrn_reflns_point_group_measured_fraction_full 0.978
_diffrn_reflns_point_group_measured_fraction_max 0.938
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.866
_diffrn_reflns_theta_min         2.270
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.226
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.68208
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.35a (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'metallic yellowish yellow'
_exptl_crystal_colour_lustre     metallic
_exptl_crystal_colour_modifier   yellowish
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.444
_exptl_crystal_description       plate
_exptl_crystal_F_000             744
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.135
_refine_diff_density_min         -0.199
_refine_diff_density_rms         0.035
_refine_ls_abs_structure_details
;
 Flack x determined using 834 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.01(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     228
_refine_ls_number_reflns         3339
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.053
_refine_ls_R_factor_all          0.0533
_refine_ls_R_factor_gt           0.0397
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0458P)^2^+0.0962P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0912
_refine_ls_wR_factor_ref         0.0994
_reflns_Friedel_coverage         0.626
_reflns_Friedel_fraction_full    0.947
_reflns_Friedel_fraction_max     0.887
_reflns_number_gt                2654
_reflns_number_total             3339
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5cc03717d2.cif
_cod_data_source_block           aks157
_cod_depositor_comments          'Adding full bibliography for 1575693.cif.'
_cod_database_code               1575693
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C H N O'
_shelx_estimated_absorpt_t_max   0.976
_shelx_estimated_absorpt_t_min   0.954
_reflns_odcompleteness_completeness 99.61
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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:
 C2(H2)
2.b Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B)
2.c Aromatic/amide H refined with riding coordinates:
 C8(H8), C12(H12), C9(H9), C13(H13), C15(H15), C16(H16)
2.d Idealised Me refined as rotating group:
 C17(H17A,H17B,H17C), C18(H18A,H18B,H18C)
;
_shelx_res_checksum              12076
_shelx_hkl_checksum              14927
_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 1.388
_oxdiff_exptl_absorpt_empirical_full_min 0.641