Visible-Light-Mediated 1,7-Enyne Bicyclizations for Synthesis of Cyclopenta[c]quinolines and Benzo[j]phenanthridines.
Gao, Fei; Yang, Chao; Ma, Na; Gao, Guo-Lin; Li, Dazhi; Xia, Wujiong; Organic letters 18 (2016) 600–603; doi:10.1021/acs.orglett.5b03662

data_1542693
_publ_section_title
;
 Visible-Light-Mediated 1,7-Enyne Bicyclizations for Synthesis of
 Cyclopenta[c]quinolines and Benzo[j]phenanthridines.
;
_journal_issue                   3
_journal_name_full               'Organic letters'
_journal_page_first              600
_journal_page_last               603
_journal_paper_doi               10.1021/acs.orglett.5b03662
_journal_volume                  18
_journal_year                    2016
_chemical_formula_moiety         'C26 H20 F3 N O'
_chemical_formula_sum            'C26 H20 F3 N O'
_chemical_formula_weight         419.43
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-I 2ya'
_space_group_name_H-M_alt        'I 1 2/a 1'
_symmetry_space_group_name_Hall  '-I 2ya'
_symmetry_space_group_name_H-M   'I 1 2/a 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2015-03-18
_audit_creation_method
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_cell_angle_alpha                90.00
_cell_angle_beta                 100.975(6)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   18.3718(11)
_cell_length_b                   5.6809(3)
_cell_length_c                   40.089(3)
_cell_measurement_reflns_used    2182
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      23.6400
_cell_measurement_theta_min      3.6140
_cell_volume                     4107.5(5)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXH-1997 (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 15.9737
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.984
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measurement_details
;
  1 omega  -53.00   67.00   1.0000   25.0000
omega____ theta____ kappa____ phi______ frames
    -       18.9630  -19.0000   60.0000 120

  2 omega  -37.00   40.00   1.0000   25.0000
omega____ theta____ kappa____ phi______ frames
    -       18.9630  -57.0000 -180.0000 77

  3 omega   22.00   49.00   1.0000   25.0000
omega____ theta____ kappa____ phi______ frames
    -       18.9630  -99.0000 -150.0000 27
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0366658000
_diffrn_orient_matrix_UB_12      0.0058328000
_diffrn_orient_matrix_UB_13      -0.0031469000
_diffrn_orient_matrix_UB_21      0.0141013000
_diffrn_orient_matrix_UB_22      -0.0318089000
_diffrn_orient_matrix_UB_23      0.0171203000
_diffrn_orient_matrix_UB_31      -0.0019232000
_diffrn_orient_matrix_UB_32      -0.1205925000
_diffrn_orient_matrix_UB_33      -0.0046667000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0260
_diffrn_reflns_av_unetI/netI     0.0407
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       4
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       48
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_number            7487
_diffrn_reflns_theta_full        25.35
_diffrn_reflns_theta_max         25.35
_diffrn_reflns_theta_min         3.11
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.101
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.91515
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_density_diffrn    1.357
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description
;
;
_exptl_crystal_F_000             1744
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.213
_refine_diff_density_min         -0.209
_refine_diff_density_rms         0.039
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     281
_refine_ls_number_reflns         3693
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.048
_refine_ls_R_factor_all          0.0892
_refine_ls_R_factor_gt           0.0589
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0455P)^2^+5.2076P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1320
_refine_ls_wR_factor_ref         0.1504
_reflns_number_gt                2485
_reflns_number_total             3693
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol5b03662_si_004.cif
_cod_data_source_block           xia-gf-2
_cod_original_cell_volume        4107.5(4)
_cod_database_code               1542693
_chemical_oxdiff_formula         'C H N O F'
_reflns_odcompleteness_completeness 98.04
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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 C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C0AA(H0AA,H0AB), C21(H21A,H21B)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C9(H9), C10(H10), C11(H11), C12(H12),
 C13(H13), C16(H16), C17(H17), C18(H18), C19(H19)
2.c Idealised Me refined as rotating group:
 C24(H24A,H24B,H24C)
;
_olex2_date_sample_data_collection 2015-03-18
_olex2_submission_special_instructions 'No special instructions were received'