Visible-Light-Promoted and Yb(OTf)3-Catalyzed Constructions of Coumarin-Pyrrole-(Iso)quinoline-Fused Pentacycles: Synthesis of Lamellarin Core, Lamellarin D Trimethyl Ether, and Lamellarin H.
Manjappa, Kiran B.; Syu, Jia-Ru; Yang, Ding-Yah; Organic letters 18 (2016) 332–335; doi:10.1021/acs.orglett.5b03524

data_1542368
_publ_section_title
;
 Visible-Light-Promoted and Yb(OTf)3-Catalyzed Constructions of
 Coumarin-Pyrrole-(Iso)quinoline-Fused Pentacycles: Synthesis of
 Lamellarin Core, Lamellarin D Trimethyl Ether, and Lamellarin H.
;
_journal_issue                   2
_journal_name_full               'Organic letters'
_journal_page_first              332
_journal_page_last               335
_journal_paper_doi               10.1021/acs.orglett.5b03524
_journal_volume                  18
_journal_year                    2016
_chemical_formula_moiety         'C19 H12 N2 O4'
_chemical_formula_sum            'C19 H12 N2 O4'
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_symmetry_space_group_name_Hall  '-P 1'
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_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                98.659(6)
_cell_angle_beta                 92.733(6)
_cell_angle_gamma                108.798(7)
_cell_formula_units_Z            2
_cell_length_a                   7.1803(5)
_cell_length_b                   8.0598(6)
_cell_length_c                   13.9214(10)
_cell_measurement_reflns_used    1731
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      29.1432
_cell_measurement_theta_min      2.8493
_cell_volume                     750.00(10)
_computing_cell_refinement
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CrysAlis RED, Oxford Diffraction Ltd., 
Version 1.171.32.29 (release 10-06-2008 CrysAlis171 .NET) 
(compiled Jun 10 2008,16:49:55) 
;
_computing_data_collection
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CrysAlis CCD, Oxford Diffraction Ltd., 
Version 1.171.32.29 (release 10-06-2008 CrysAlis171 .NET) 
(compiled Jun 10 2008,16:49:55) 
;
_computing_data_reduction
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CrysAlis RED, Oxford Diffraction Ltd., 
Version 1.171.32.29 (release 10-06-2008 CrysAlis171 .NET) 
(compiled Jun 10 2008,16:49:55) 
;
_computing_molecular_graphics    'Bruker SHELXTL'
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_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.839
_diffrn_measurement_device_type  'CCD detector'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0291
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_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       18
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_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         29.21
_diffrn_reflns_theta_min         2.86
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.105
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.98644
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CrysAlisPro, Agilent Technologies, 
Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET) 
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Empirical absorption correction using spherical harmonics, 
 implemented in SCALE3 ABSPACK scaling algorithm. 
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.471
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       parallelepiped
_exptl_crystal_F_000             344
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.36
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.269
_refine_diff_density_min         -0.215
_refine_diff_density_rms         0.048
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.123
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     226
_refine_ls_number_reflns         3408
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.123
_refine_ls_R_factor_all          0.0680
_refine_ls_R_factor_gt           0.0463
_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^)+(0.0495P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1050
_refine_ls_wR_factor_ref         0.1178
_reflns_number_gt                2542
_reflns_number_total             3408
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol5b03524_si_003.cif
_cod_data_source_block           gr073
_cod_original_cell_volume        750.00(9)
_cod_database_code               1542368