Synthesis of Benzoindolizines through 1,5-Electrocyclization/Oxidation Cascades.
Liu, Si-Wei; Gao, Ying-Juan; Shi, Yin; Zhou, Lin; Tang, Xue; Cui, Hai-Lei; The Journal of organic chemistry 83 (2018) 13754–13764; doi:10.1021/acs.joc.8b02065

data_4034836
_publ_section_title
;
 Synthesis of Benzoindolizines through 1,5-Electrocyclization/Oxidation
 Cascades.
;
_journal_issue                   22
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              13754
_journal_page_last               13764
_journal_paper_doi               10.1021/acs.joc.8b02065
_journal_volume                  83
_journal_year                    2018
_chemical_formula_moiety         'C22 H19 N O4'
_chemical_formula_sum            'C22 H19 N O4'
_chemical_formula_weight         361.38
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2017-12-05
_audit_creation_method
;
Olex2 1.2-beta
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_cell_angle_alpha                90
_cell_angle_beta                 109.509(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   13.8760(16)
_cell_length_b                   8.3029(10)
_cell_length_c                   16.3492(19)
_cell_measurement_reflns_used    3663
_cell_measurement_temperature    296.15
_cell_measurement_theta_max      27.334
_cell_measurement_theta_min      2.582
_cell_volume                     1775.5(4)
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_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_temperature      296.15
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.974
_diffrn_measurement_device_type  'CCD Area Detector'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0333
_diffrn_reflns_av_unetI/netI     0.0379
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.974
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            10271
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.974
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.561
_diffrn_reflns_theta_min         2.787
_exptl_absorpt_coefficient_mu    0.093
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.5573
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2014/3 (Bruker,2014/3) was used for absorption correction.
wR2(int) was 0.0995 before and 0.0419 after correction.
The Ratio of minimum to maximum transmission is 0.7475.
The \l/2 correction factor is 0.00150.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.352
_exptl_crystal_description       block
_exptl_crystal_F_000             760
_refine_diff_density_max         0.257
_refine_diff_density_min         -0.171
_refine_diff_density_rms         0.039
_refine_ls_extinction_coef       0.0132(15)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.021
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     248
_refine_ls_number_reflns         3993
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.021
_refine_ls_R_factor_all          0.0732
_refine_ls_R_factor_gt           0.0438
_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^)+(0.0530P)^2^+0.4514P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1060
_refine_ls_wR_factor_ref         0.1241
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2776
_reflns_number_total             3993
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo8b02065_si_002.cif
_cod_data_source_block           chlchcl3_0m
_cod_database_code               4034836
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C7(H7), C10(H10), C13(H13), C14(H14), C15(H15), C18(H18), C19(H19),
 C20(H20), C21(H21)
2.b Idealised Me refined as rotating group:
 C9(H9A,H9B,H9C), C12(H12A,H12B,H12C), C22(H22A,H22B,H22C)
;
_shelx_res_checksum              84385
_shelx_hkl_checksum              1227
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'