C(3)-Aryl isoindolinones: a PTSA-mediated access and improved synthesis of (±)-nuevamine
Rao, H. Surya Prakash; J, Prabhakaran; New Journal of Chemistry 47 (2023) 19283–19288; doi:10.1039/D3NJ03498D

data_7062735
_publ_section_title
;
 C(3)-Aryl isoindolinones: a PTSA-mediated access and improved synthesis
 of (+-)-nuevamine
;
_journal_issue                   41
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              19283
_journal_page_last               19288
_journal_paper_doi               10.1039/D3NJ03498D
_journal_volume                  47
_journal_year                    2023
_chemical_absolute_configuration unk
_chemical_formula_moiety         'C19 H17 N O5'
_chemical_formula_sum            'C19 H17 N O5'
_chemical_formula_weight         339.33
_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     direct
_audit_creation_date             2019-11-02
_audit_creation_method
;
Olex2 1.3-alpha
(compiled 2019.09.11 svn.r3662 for OlexSys, GUI svn.r5938)
;
_audit_update_record
;
2019-11-02 deposited with the CCDC.	2023-09-20 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.6688(5)
_cell_length_b                   11.5902(5)
_cell_length_c                   12.7186(5)
_cell_measurement_reflns_used    2046
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      29.1719
_cell_measurement_theta_min      3.0434
_cell_volume                     1572.70(12)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET)
(compiled Sep 14 2012,17:21:16)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET)
(compiled Sep 14 2012,17:21:16)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET)
(compiled Sep 14 2012,17:21:16)
;
_computing_molecular_graphics    'Olex2 1.3-alpha (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3-alpha (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS n/a (Sheldrick, 2008)'
_diffrn_ambient_temperature      298(2)
_diffrn_detector_area_resol_mean 15.9821
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.876
_diffrn_measurement_details
;
  1 omega   -6.00   24.00   1.0000   26.8500
omega____ theta____ kappa____ phi______ frames
    -      -17.0272  -99.0000   90.0000 30

  2 omega  -61.00  -18.00   1.0000   26.8500
omega____ theta____ kappa____ phi______ frames
    -      -17.0272  -19.0000    0.0000 43

  3 omega   14.00   87.00   1.0000   26.8500
omega____ theta____ kappa____ phi______ frames
    -       19.6835   57.0000 -180.0000 73

  4 omega  -38.00  -13.00   1.0000   26.8500
omega____ theta____ kappa____ phi______ frames
    -      -17.0272   57.0000  150.0000 25
;
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0385049000
_diffrn_orient_matrix_UB_12      0.0486842000
_diffrn_orient_matrix_UB_13      0.0097370000
_diffrn_orient_matrix_UB_21      -0.0516242000
_diffrn_orient_matrix_UB_22      -0.0370237000
_diffrn_orient_matrix_UB_23      0.0100976000
_diffrn_orient_matrix_UB_31      0.0166076000
_diffrn_orient_matrix_UB_32      -0.0019696000
_diffrn_orient_matrix_UB_33      0.0539567000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0160
_diffrn_reflns_av_unetI/netI     0.0271
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.876
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            5586
_diffrn_reflns_point_group_measured_fraction_full 0.887
_diffrn_reflns_point_group_measured_fraction_max 0.745
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.236
_diffrn_reflns_theta_min         3.050
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.105
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.88108
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET)
(compiled Sep 14 2012,17:21:16)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            red
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.433
_exptl_crystal_description       plate
_exptl_crystal_F_000             712
_exptl_crystal_size_max          0.56
_exptl_crystal_size_mid          0.46
_exptl_crystal_size_min          0.26
_refine_diff_density_max         0.148
_refine_diff_density_min         -0.132
_refine_diff_density_rms         0.029
_refine_ls_abs_structure_details
;
 Flack x determined using 792 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.9(7)
_refine_ls_extinction_coef       0.0073(17)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     229
_refine_ls_number_reflns         3186
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.056
_refine_ls_R_factor_all          0.0478
_refine_ls_R_factor_gt           0.0368
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0439P)^2^+0.1257P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0867
_refine_ls_wR_factor_ref         0.0950
_reflns_Friedel_coverage         0.499
_reflns_Friedel_fraction_full    0.735
_reflns_Friedel_fraction_max     0.573
_reflns_number_gt                2685
_reflns_number_total             3186
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3nj03498d2.cif
_cod_data_source_block           hsp-jp-new-as
_cod_depositor_comments          'Adding full bibliography for 7062735.cif.'
_cod_original_cell_volume        1572.71(12)
_cod_database_code               7062735
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C19 H17 N O5'
_chemical_oxdiff_usercomment     'RED COLOUR PLATE, 298K, 0.56 0.46 0.26'
_shelx_estimated_absorpt_t_max   0.973
_shelx_estimated_absorpt_t_min   0.944
_reflns_odcompleteness_completeness 99.68
_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:
 C9(H9)
2.b Secondary CH2 refined with riding coordinates:
 C19(H19A,H19B), C20(H20A,H20B), C21(H21A,H21B)
2.c Aromatic/amide H refined with riding coordinates:
 C12(H12), C16(H16), C22(H22), C24(H24)
2.d Idealised Me refined as rotating group:
 C(HA,HB,HC), C25(H25A,H25B,H25C)
;
_shelx_res_checksum              85669
_olex2_submission_special_instructions 'No special instructions were received'