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_1542694
_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         'C29 H25 F2 N O3'
_chemical_formula_sum            'C29 H25 F2 N O3'
_chemical_formula_weight         473.50
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_audit_creation_date             2015-04-24
_audit_creation_method
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_cell_angle_alpha                71.454(5)
_cell_angle_beta                 71.195(6)
_cell_angle_gamma                73.002(6)
_cell_formula_units_Z            2
_cell_length_a                   10.2357(7)
_cell_length_b                   10.5168(6)
_cell_length_c                   12.7893(6)
_cell_measurement_reflns_used    2847
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.6100
_cell_measurement_theta_min      3.5820
_cell_volume                     1207.61(13)
_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
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CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction
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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  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_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 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_details
;
  1 omega  -50.00    0.00   1.0000    3.5000
omega____ theta____ kappa____ phi______ frames
    -       18.9630  -57.0000    0.0000 50

  2 omega    1.00   62.00   1.0000    3.5000
omega____ theta____ kappa____ phi______ frames
    -       18.9630  -99.0000  -60.0000 61

  3 omega   21.00   60.00   1.0000    3.5000
omega____ theta____ kappa____ phi______ frames
    -       18.9630  -99.0000  150.0000 39

  4 omega  -55.00   56.00   1.0000    3.5000
omega____ theta____ kappa____ phi______ frames
    -       18.9630  -19.0000   60.0000 111

  5 omega   -6.00   61.00   1.0000    3.5000
omega____ theta____ kappa____ phi______ frames
    -       18.9630   77.0000   60.0000 67

  6 omega   21.00   87.00   1.0000    3.5000
omega____ theta____ kappa____ phi______ frames
    -       18.9630   57.0000 -120.0000 66
;
_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      0.0419719000
_diffrn_orient_matrix_UB_12      -0.0651150000
_diffrn_orient_matrix_UB_13      0.0192596000
_diffrn_orient_matrix_UB_21      0.0615442000
_diffrn_orient_matrix_UB_22      0.0278047000
_diffrn_orient_matrix_UB_23      -0.0252500000
_diffrn_orient_matrix_UB_31      -0.0077755000
_diffrn_orient_matrix_UB_32      0.0168694000
_diffrn_orient_matrix_UB_33      0.0514544000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0200
_diffrn_reflns_av_unetI/netI     0.0357
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            8170
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.348
_diffrn_reflns_theta_min         3.087
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.094
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.88721
_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    1.302
_exptl_crystal_description
;
;
_exptl_crystal_F_000             496
_refine_diff_density_max         0.291
_refine_diff_density_min         -0.213
_refine_diff_density_rms         0.038
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     318
_refine_ls_number_reflns         4426
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.028
_refine_ls_R_factor_all          0.0789
_refine_ls_R_factor_gt           0.0566
_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^+0.4571P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1365
_refine_ls_wR_factor_ref         0.1541
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3199
_reflns_number_total             4426
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol5b03662_si_003.cif
_cod_data_source_block           xwj-gf20150407
_cod_original_cell_volume        1207.62(14)
_cod_database_code               1542694
_chemical_oxdiff_formula         'c h n o s'
_reflns_odcompleteness_completeness 99.84
_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:
 C22(H22A,H22B), C24(H24A,H24B), C26(H26A,H26B)
2.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C5(H5), C6(H6), C7(H7), C9(H9), C10(H10), C11(H11), C12(H12),
 C15(H15), C16(H16), C17(H17), C18(H18)
2.c Idealised Me refined as rotating group:
 C27(H27A,H27B,H27C), C28(H28A,H28B,H28C)
;
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'