Synthesis of tricyclic oxazinoindolones <i>via</i> Pd-catalyzed intramolecular addition of carboxylic acids to alkynes.
Mukhopadhyay, Subhamoy; Khaitan, Bhavya; Gandhi, Shikha; Organic & biomolecular chemistry 21 (2023) 9326–9329; doi:10.1039/d3ob01672b

data_7159682
_publ_section_title
;
 Synthesis of tricyclic oxazinoindolones <i>via</i> Pd-catalyzed
 intramolecular addition of carboxylic acids to alkynes.
;
_journal_issue                   47
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              9326
_journal_page_last               9329
_journal_paper_doi               10.1039/d3ob01672b
_journal_volume                  21
_journal_year                    2023
_chemical_formula_moiety         'C18 H13 N O2'
_chemical_formula_sum            'C18 H13 N O2'
_chemical_formula_weight         275.309
_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'
_symmetry_Int_Tables_number      14
_atom_sites_solution_primary     iterative
_audit_creation_date             2023-03-16
_audit_creation_method
;
Olex2 1.5-beta
(compiled 2023.03.06 svn.rbb2c1857 for OlexSys, GUI svn.r6748)
;
_audit_update_record
;
2023-04-15 deposited with the CCDC.	2023-11-14 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 96.294(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.4846(2)
_cell_length_b                   6.6085(2)
_cell_length_c                   27.8900(8)
_cell_measurement_reflns_used    6126
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      78.3490
_cell_measurement_theta_min      5.9480
_cell_volume                     1371.18(7)
_computing_cell_refinement       'CrysAlisPro 1.171.42.52a (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.52a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.52a (Rigaku OD, 2022)'
_computing_molecular_graphics    'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine 1.5-beta (Bourhis et al., 2015)'
_computing_structure_solution    'olex2.solve 1.5-beta (Bourhis et al., 2015)'
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector_area_resol_mean 5.8140
_diffrn_detector_type            'Pilatus 200K'
_diffrn_measured_fraction_theta_full 0.9976
_diffrn_measured_fraction_theta_max 0.9846
_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    -75.00  15.00   0.50    0.49    --  -38.50 100.00  52.00  180
  2  \w      7.00  86.00   0.50    0.49    --   49.31-100.00 -52.00  158
  3  \w     42.00 107.00   0.50    0.99    --  111.00-100.00 -52.00  130
  4  \w    104.00 178.00   0.50    0.99    --  111.00 100.00  52.00  148
  5  \w   -101.00 -27.00   0.50    0.49    --  -38.50 -57.00 -30.00  148
  6  \w    -42.00  28.00   0.50    0.49    --  -38.50  37.00-150.00  140
  7  \w    -42.00  28.00   0.50    0.49    --  -38.50  37.00 -30.00  140
  8  \w     46.00 116.00   0.50    0.49    --   49.31  37.00-120.00  140
  9  \w     43.00 114.00   0.50    0.99    --  111.00 -30.00  60.00  142
 10  \w    103.00 176.00   0.50    0.99    --  111.00  77.00  30.00  146
 11  \w    107.00 176.00   0.50    0.99    --  111.00  45.00 -60.00  138
 12  \w     48.00 124.00   0.50    0.99    --  111.00 -61.00-180.00  152
 13  \w    108.00 178.00   0.50    0.99    --  111.00  30.00  90.00  140
 14  \w    107.00 176.00   0.50    0.99    --  111.00  45.00-180.00  138
 15  \w     42.00 109.00   0.50    0.99    --  111.00-111.00  60.00  134
 16  \w     47.00 116.00   0.50    0.99    --  111.00 -45.00-120.00  138
 17  \w     47.00 116.00   0.50    0.99    --  111.00 -45.00 150.00  138
 18  \w     43.00 104.00   0.50    0.99    --  111.00-111.00 120.00  122
 19  \w     70.00 104.00   0.50    0.99    --  111.00 -94.00 120.00   68
 20  \w     55.00 118.00   0.50    0.99    --  111.00 -15.00 120.00  126
 21  \w     48.00 114.00   0.50    0.99    --  111.00 -45.00  60.00  132
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type
'SuperNova, Dual, Cu at home/near, Pilatus 200K'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0467
_diffrn_reflns_av_unetI/netI     0.0410
_diffrn_reflns_Laue_measured_fraction_full 0.9976
_diffrn_reflns_Laue_measured_fraction_max 0.9846
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       35
_diffrn_reflns_limit_l_min       -35
_diffrn_reflns_number            11916
_diffrn_reflns_point_group_measured_fraction_full 0.9976
_diffrn_reflns_point_group_measured_fraction_max 0.9846
_diffrn_reflns_theta_full        67.6840
_diffrn_reflns_theta_max         79.27
_diffrn_reflns_theta_min         5.99
_exptl_absorpt_coefficient_mu    0.702
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.38727
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.42.52a (Rigaku Oxford Diffraction, 2022)
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    1.334
_exptl_crystal_description       plate
_exptl_crystal_F_000             577.932
_exptl_crystal_preparation       'As per the reaction scheme'
_exptl_crystal_recrystallization_method 'Slow vapour diffusion'
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.29
_exptl_crystal_size_min          0.16
_refine_diff_density_max         0.4363
_refine_diff_density_min         -0.3103
_refine_diff_density_rms         0.0769
_refine_ls_d_res_high            0.7846
_refine_ls_d_res_low             7.3910
_refine_ls_goodness_of_fit_ref   1.1492
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    25
_refine_ls_number_parameters     190
_refine_ls_number_reflns         2932
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.1492
_refine_ls_R_factor_all          0.0698
_refine_ls_R_factor_gt           0.0648
_refine_ls_shift/su_max          -0.0003
_refine_ls_shift/su_mean         0.0001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0175P)^2^+2.3798P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1493
_refine_ls_wR_factor_ref         0.1518
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              8
_reflns_limit_h_min              -9
_reflns_limit_k_max              8
_reflns_limit_k_min              0
_reflns_limit_l_max              35
_reflns_limit_l_min              -7
_reflns_number_gt                2636
_reflns_number_total             2932
_reflns_threshold_expression     I>=2u(I)
_cod_data_source_file            d3ob01672b2.cif
_cod_data_source_block           sjp-smc-pm_auto
_cod_depositor_comments          'Adding full bibliography for 7159682.cif.'
_cod_database_code               7159682
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C3(H3a,H3b)
2.b Aromatic/amide H refined with riding coordinates:
 C9(H9), C14(H14), C8(H8), C11(H11), C17(H17), C16(H16), C12(H12), C15(H15),
 C10(H10), C18(H18), C5(H5)
;
_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
;