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_1534098
_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         'C26 H21 N O3'
_chemical_formula_sum            'C26 H21 N O3'
_chemical_formula_weight         395.44
_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
_atom_sites_solution_primary     direct
_audit_creation_date             2015-04-29
_audit_creation_method
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_cell_angle_alpha                90
_cell_angle_beta                 96.804(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.5406(12)
_cell_length_b                   9.3427(10)
_cell_length_c                   18.9135(16)
_cell_measurement_reflns_used    5654
_cell_measurement_temperature    303.7
_cell_measurement_theta_max      23.93
_cell_measurement_theta_min      2.43
_cell_volume                     2024.9(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)'
_computing_structure_solution    'XT (Sheldrick, 2015)'
_diffrn_ambient_temperature      303.7
_diffrn_measured_fraction_theta_full 0.999
_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  0.1036
_diffrn_reflns_av_unetI/netI     0.0495
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            34704
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         26.057
_diffrn_reflns_theta_min         2.435
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.085
_exptl_absorpt_correction_T_max  0.7453
_exptl_absorpt_correction_T_min  0.6694
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2014/4 (Bruker,2014/4) was used for absorption correction.
wR2(int) was 0.0666 before and 0.0600 after correction.
The Ratio of minimum to maximum transmission is 0.8982.
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    1.297
_exptl_crystal_description       block
_exptl_crystal_F_000             832
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.143
_refine_diff_density_min         -0.171
_refine_diff_density_rms         0.035
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     283
_refine_ls_number_reflns         3999
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.032
_refine_ls_R_factor_all          0.1088
_refine_ls_R_factor_gt           0.0511
_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^)+(0.0475P)^2^+0.3001P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1001
_refine_ls_wR_factor_ref         0.1187
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2365
_reflns_number_total             3999
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol5b02331_si_001.cif
_cod_data_source_block           7a
_cod_database_code               1534098
_olex2_refinement_description
;
1. Others
 Fixed Uiso: H5(0.064) H6(0.073) H7(0.075) H8(0.066) H13A(0.089) H13B(0.089)
 H14A(0.124) H14B(0.124) H14C(0.124) H16(0.073) H17(0.089) H18(0.095)
 H19(0.085) H21(0.07) H24(0.067) H25(0.069) H27(0.061) H28(0.06) H30A(0.133)
 H30B(0.133) H30C(0.133)
 Fixed X: H5(0.1943) H6(0.0984) H7(0.0884) H8(0.1754) H13A(0.2173)
 H13B(0.3248) H14A(0.1629) H14B(0.2013) H14C(0.0931) H16(0.4538) H17(0.5658)
 H18(0.5997) H19(0.524) H21(0.401) H24(0.3872) H25(0.2869) H27(-0.0147)
 H28(0.0858) H30A(0.1595) H30B(0.0554) H30C(0.1631)
 Fixed Y: H5(0.5028) H6(0.6996) H7(0.9046) H8(0.9088) H13A(0.9564)
 H13B(1.0332) H14A(1.186) H14B(1.1588) H14C(1.0778) H16(0.5665) H17(0.4073)
 H18(0.1787) H19(0.1102) H21(0.1529) H24(0.202) H25(0.0957) H27(0.1942)
 H28(0.295) H30A(-0.0811) H30B(-0.0547) H30C(0.0487)
 Fixed Z: H5(0.6302) H6(0.6625) H7(0.5915) H8(0.4898) H13A(0.2834)
 H13B(0.3264) H14A(0.3103) H14B(0.3915) H14C(0.3525) H16(0.3298) H17(0.2751)
 H18(0.3193) H19(0.4199) H21(0.5124) H24(0.6549) H25(0.7391) H27(0.6228)
 H28(0.5377) H30A(0.7731) H30B(0.8177) H30C(0.8259)
;
_shelx_res_checksum              53167
_shelx_hkl_checksum              61005
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'