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_1542692
_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         'C32 H31 N O5'
_chemical_formula_sum            'C32 H31 N O5'
_chemical_formula_weight         509.58
_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             2015-10-06
_audit_creation_method
;
Olex2 1.2
(compiled 2015.09.30 svn.r3233 for OlexSys, GUI svn.r5103)
;
_cell_angle_alpha                90
_cell_angle_beta                 94.816(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.3073(5)
_cell_length_b                   11.8581(5)
_cell_length_c                   21.8138(8)
_cell_measurement_reflns_used    3550
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      26.6890
_cell_measurement_theta_min      3.9540
_cell_volume                     2656.8(2)
_computing_cell_refinement       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_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      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 15.9737
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

--------------------------------------------------------------------------
  1  \w     -2.00  50.00   1.00   12.50    --   18.81  57.00 -30.00   52
  2  \w      0.00  87.00   1.00   12.50    --   18.81  77.00   0.00   87
  3  \w    -50.00  47.00   1.00   12.50    --  -19.74  77.00  60.00   97
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0183742000
_diffrn_orient_matrix_UB_12      -0.0576783000
_diffrn_orient_matrix_UB_13      0.0018091000
_diffrn_orient_matrix_UB_21      -0.0636136000
_diffrn_orient_matrix_UB_22      -0.0157608000
_diffrn_orient_matrix_UB_23      -0.0118752000
_diffrn_orient_matrix_UB_31      0.0196456000
_diffrn_orient_matrix_UB_32      0.0027175000
_diffrn_orient_matrix_UB_33      -0.0303184000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0245
_diffrn_reflns_av_unetI/netI     0.0331
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            10135
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.350
_diffrn_reflns_theta_max         25.350
_diffrn_reflns_theta_min         3.126
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.086
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.94077
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.41 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.274
_exptl_crystal_description       block
_exptl_crystal_F_000             1080
_refine_diff_density_max         0.614
_refine_diff_density_min         -0.294
_refine_diff_density_rms         0.042
_refine_ls_extinction_coef       0.0055(9)
_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   1.020
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     347
_refine_ls_number_reflns         4840
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.020
_refine_ls_R_factor_all          0.0778
_refine_ls_R_factor_gt           0.0605
_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^)+(0.0630P)^2^+1.8115P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1494
_refine_ls_wR_factor_ref         0.1627
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3672
_reflns_number_total             4840
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol5b03662_si_002.cif
_cod_data_source_block           151005
_cod_original_cell_volume        2656.77(19)
_cod_database_code               1542692
_chemical_oxdiff_formula         'C H O N'
_reflns_odcompleteness_completeness 99.72
_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 Ternary CH refined with riding coordinates:
 C24(H24)
2.b Secondary CH2 refined with riding coordinates:
 C17(H17A,H17B), C25(H25A,H25B), C27(H27A,H27B), C30(H30A,H30B)
2.c Aromatic/amide H refined with riding coordinates:
 C3(H3), C6(H6), C7(H7), C8(H8), C12(H12), C13(H13), C14(H14), C15(H15),
 C19(H19), C20(H20), C21(H21), C22(H22), C23(H23)
2.d Idealised Me refined as rotating group:
 C2(H2A,H2B,H2C), C28(H28A,H28B,H28C), C31(H31A,H31B,H31C)
;
_shelx_res_checksum              70332
_shelx_hkl_checksum              37701
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.196
_oxdiff_exptl_absorpt_empirical_full_min 0.857