Facile synthesis of indolizinoindolone, indolylepoxypyrrolooxazole, indolylpyrrolooxazolone and isoindolopyrazinoindolone heterocycles from indole and imide derivatives.
Shelar, Santosh V.; Argade, Narshinha P.; Organic & biomolecular chemistry 19 (2021) 6160–6169; doi:10.1039/d1ob00754h

data_7158132
_publ_section_title
;
 Facile synthesis of indolizinoindolone, indolylepoxypyrrolooxazole,
 indolylpyrrolooxazolone and isoindolopyrazinoindolone heterocycles from
 indole and imide derivatives.
;
_journal_issue                   27
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              6160
_journal_page_last               6169
_journal_paper_doi               10.1039/d1ob00754h
_journal_volume                  19
_journal_year                    2021
_chemical_formula_moiety         'C14 H14 N2 O2'
_chemical_formula_sum            'C14 H14 N2 O2'
_chemical_formula_weight         242.27
_space_group_crystal_system      orthorhombic
_space_group_IT_number           29
_space_group_name_Hall           'P 2c -2ac'
_space_group_name_H-M_alt        'P c a 21'
_atom_sites_solution_hydrogens   mixed
_audit_creation_date             2021-01-11
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2021-03-17 deposited with the CCDC.	2021-06-21 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   24.406(2)
_cell_length_b                   5.0265(4)
_cell_length_c                   9.4136(8)
_cell_measurement_reflns_used    9952
_cell_measurement_temperature    100
_cell_measurement_theta_max      27.18
_cell_measurement_theta_min      2.73
_cell_volume                     1154.83(16)
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_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 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      100.0
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0601
_diffrn_reflns_av_unetI/netI     0.0234
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       31
_diffrn_reflns_limit_h_min       -31
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            38269
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.359
_diffrn_reflns_theta_min         1.669
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.095
_exptl_absorpt_correction_T_max  0.7455
_exptl_absorpt_correction_T_min  0.6874
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.1020 before and 0.0670 after correction.
The Ratio of minimum to maximum transmission is 0.9221.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.393
_exptl_crystal_description       block
_exptl_crystal_F_000             512
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.265
_refine_diff_density_min         -0.248
_refine_diff_density_rms         0.075
_refine_ls_abs_structure_details
;
 Flack x determined using 1127 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.5(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.193
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     169
_refine_ls_number_reflns         2610
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.194
_refine_ls_R_factor_all          0.0390
_refine_ls_R_factor_gt           0.0358
_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^)+(0.0622P)^2^+0.2327P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0960
_refine_ls_wR_factor_ref         0.1060
_reflns_Friedel_coverage         0.878
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.994
_reflns_number_gt                2525
_reflns_number_total             2610
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1ob00754h2.cif
_cod_data_source_block           9
_cod_depositor_comments
'Adding full bibliography for 7158131--7158132.cif.'
_cod_original_cell_volume        1154.83(17)
_cod_database_code               7158132
_shelx_shelxl_version_number     2016/6
_shelx_estimated_absorpt_t_max   0.994
_shelx_estimated_absorpt_t_min   0.983
_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 O(H) groups
2. Restrained distances
 N2-H2A
 0.87 with sigma of 0.02
3.a Ternary CH refined with riding coordinates:
 C4(H4), C13(H13)
3.b Secondary CH2 refined with riding coordinates:
 C14(H14A,H14B), C3(H3A,H3B), C2(H2B,H2C)
3.c Aromatic/amide H refined with riding coordinates:
 C8(H8), C9(H9), C7(H7), C10(H10)
3.d Idealised tetrahedral OH refined as rotating group with stretchable bonds:
 O2(H2)
;
_shelx_res_checksum              52885
_olex2_submission_special_instructions 'No special instructions were received'