Acid-Mediated Intermolecular [3 + 2] Cycloaddition toward Pyrrolo[2,1-a]isoquinolines: Total Synthesis of the Lamellarin Core and Lamellarin G Trimethyl Ether.
Zheng, Kai-Lu; You, Min-Qi; Shu, Wen-Ming; Wu, Yan-Dong; Wu, An-Xin; Organic letters 19 (2017) 2262–2265; doi:10.1021/acs.orglett.7b00769

data_1545758
_publ_section_title
;
 Acid-Mediated Intermolecular [3 + 2] Cycloaddition toward
 Pyrrolo[2,1-a]isoquinolines: Total Synthesis of the Lamellarin Core and
 Lamellarin G Trimethyl Ether.
;
_journal_issue                   9
_journal_name_full               'Organic letters'
_journal_page_first              2262
_journal_page_last               2265
_journal_paper_doi               10.1021/acs.orglett.7b00769
_journal_volume                  19
_journal_year                    2017
_chemical_formula_sum            'C25 H20.5 Cl2.5 N O2'
_chemical_formula_weight         455.55
_space_group_crystal_system      monoclinic
_space_group_IT_number           9
_space_group_name_Hall           'C -2yc'
_space_group_name_H-M_alt        'C 1 c 1'
_symmetry_space_group_name_Hall  'C -2yc'
_symmetry_space_group_name_H-M   'C 1 c 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 98.140(2)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   13.7789(19)
_cell_length_b                   14.858(2)
_cell_length_c                   22.728(3)
_cell_measurement_reflns_used    6907
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      27.28
_cell_measurement_theta_min      2.57
_cell_volume                     4606.2(11)
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  CCD
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0267
_diffrn_reflns_av_unetI/netI     0.0452
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_number            23326
_diffrn_reflns_point_group_measured_fraction_full 0.906
_diffrn_reflns_point_group_measured_fraction_max 0.868
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.295
_diffrn_reflns_theta_min         1.810
_exptl_absorpt_coefficient_mu    0.361
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.314
_exptl_crystal_description       Block
_exptl_crystal_F_000             1888
_exptl_crystal_size_max          0.220
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.180
_exptl_transmission_factor_max   0.864
_exptl_transmission_factor_min   0.864
_refine_diff_density_max         0.670
_refine_diff_density_min         -0.292
_refine_diff_density_rms         0.069
_refine_ls_abs_structure_details
;
 Flack x determined using 2915 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.19(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.981
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     597
_refine_ls_number_reflns         11990
_refine_ls_number_restraints     95
_refine_ls_restrained_S_all      1.005
_refine_ls_R_factor_all          0.0938
_refine_ls_R_factor_gt           0.0679
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1634P)^2^+0.0595P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1974
_refine_ls_wR_factor_ref         0.2268
_reflns_Friedel_coverage         0.740
_reflns_Friedel_fraction_full    0.814
_reflns_Friedel_fraction_max     0.739
_reflns_number_gt                8413
_reflns_number_total             11990
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol7b00769_si_002.cif
_cod_data_source_block           1_a
_cod_depositor_comments
;
Adding full bibliography for 1545758--1545759.cif.

2019-08-15
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_cell_volume        4605.9(11)
_cod_original_formula_sum        'C50 H41 Cl5 N2 O4'
_cod_original_formula_units_Z    4
_cod_original_formula_weight     911.10
_cod_database_code               1545758
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.925
_shelx_estimated_absorpt_t_max   0.938
_shelx_res_checksum              5872
_shelx_hkl_checksum              75023