Deformylative Intramolecular Hydroarylation: Synthesis of Benzo[e]pyrido[1,2-a]indoles.
Jung, Youngeun; Kim, Ikyon; Organic letters 17 (2015) 4600–4603; doi:10.1021/acs.orglett.5b02331

data_1534097
_publ_section_title
;
 Deformylative Intramolecular Hydroarylation: Synthesis of
 Benzo[e]pyrido[1,2-a]indoles.
;
_journal_issue                   18
_journal_name_full               'Organic letters'
_journal_page_first              4600
_journal_page_last               4603
_journal_paper_doi               10.1021/acs.orglett.5b02331
_journal_volume                  17
_journal_year                    2015
_chemical_formula_moiety         'C27 H21 N O4'
_chemical_formula_sum            'C27 H21 N O4'
_chemical_formula_weight         423.45
_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'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2015-05-11
_audit_creation_method
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_cell_angle_alpha                90
_cell_angle_beta                 92.216(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.7836(12)
_cell_length_b                   8.1908(7)
_cell_length_c                   21.1196(19)
_cell_measurement_reflns_used    9919
_cell_measurement_temperature    99.9
_cell_measurement_theta_max      26.01
_cell_measurement_theta_min      2.54
_cell_volume                     2036.9(3)
_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  'XL (Sheldrick, 2008)'
_diffrn_ambient_temperature      99.9
_diffrn_measured_fraction_theta_full 0.966
_diffrn_measured_fraction_theta_max 0.958
_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  0.0474
_diffrn_reflns_av_unetI/netI     0.0314
_diffrn_reflns_Laue_measured_fraction_full 0.966
_diffrn_reflns_Laue_measured_fraction_max 0.958
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            25901
_diffrn_reflns_point_group_measured_fraction_full 0.966
_diffrn_reflns_point_group_measured_fraction_max 0.958
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         26.155
_diffrn_reflns_theta_min         2.542
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.093
_exptl_absorpt_correction_T_max  0.7453
_exptl_absorpt_correction_T_min  0.7068
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2014/4 (Bruker,2014/4) was used for absorption correction.
wR2(int) was 0.0588 before and 0.0547 after correction.
The Ratio of minimum to maximum transmission is 0.9483.
The \l/2 correction factor is 0.00150.
;
_exptl_crystal_colour            'clear dark yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   dark
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.381
_exptl_crystal_description       block
_exptl_crystal_F_000             888
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.258
_refine_diff_density_min         -0.229
_refine_diff_density_rms         0.047
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.072
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     291
_refine_ls_number_reflns         3893
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.072
_refine_ls_R_factor_all          0.0479
_refine_ls_R_factor_gt           0.0366
_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^)+(0.0382P)^2^+1.1084P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0843
_refine_ls_wR_factor_ref         0.0961
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3245
_reflns_number_total             3893
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol5b02331_si_002.cif
_cod_data_source_block           4a
_cod_database_code               1534097
_olex2_refinement_description
;
1. Others
 Fixed Uiso: H5(0.024) H6(0.026) H7(0.028) H8(0.025) H13A(0.031) H13B(0.031)
 H14A(0.052) H14B(0.052) H14C(0.052) H15(0.021) H19(0.025) H20(0.028)
 H21(0.029) H22(0.026) H26(0.026) H27(0.029) H29(0.023) H30(0.022) H32A(0.04)
 H32B(0.04) H32C(0.04)
 Fixed X: H5(0.2932) H6(0.368) H7(0.5633) H8(0.6804) H13A(0.9304) H13B(0.9048)
 H14A(0.946) H14B(0.9784) H14C(1.0539) H15(0.2413) H19(0.6651) H20(0.6402)
 H21(0.4581) H22(0.303) H26(-0.0473) H27(-0.1776) H29(0.0762) H30(0.2064) H32A(-
 0.0837) H32B(-0.1848) H32C(-0.0612)
 Fixed Y: H5(0.6252) H6(0.5108) H7(0.5423) H8(0.6858) H13A(0.9174)
 H13B(0.9307) H14A(0.6478) H14B(0.6422) H14C(0.7469) H15(0.7592) H19(1.0304)
 H20(1.1746) H21(1.2035) H22(1.0847) H26(0.9431) H27(0.7351) H29(0.3996)
 H30(0.6107) H32A(0.2473) H32B(0.1988) H32C(0.2387)
 Fixed Z: H5(0.4621) H6(0.3732) H7(0.3544) H8(0.4247) H13A(0.5409)
 H13B(0.4657) H14A(0.4564) H14B(0.5306) H14C(0.4841) H15(0.5568) H19(0.6542)
 H20(0.7466) H21(0.7869) H22(0.7351) H26(0.6648) H27(0.677) H29(0.6717)
 H30(0.6575) H32A(0.6346) H32B(0.6795) H32C(0.7098)
;
_shelx_res_checksum              82889
_shelx_hkl_checksum              52563
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'