Total Syntheses of Chelidonine and Norchelidonine via an Enamide-Benzyne-[2 + 2] Cycloaddition Cascade.
Ma, Zhi-Xiong; Feltenberger, John B.; Hsung, Richard P.; Organic letters 14 (2012) 2742–2745; doi:10.1021/ol300967a

data_1507719
_publ_section_title
;
 Total Syntheses of Chelidonine and Norchelidonine via an
 Enamide-Benzyne-[2 + 2] Cycloaddition Cascade.
;
_journal_issue                   11
_journal_name_full               'Organic letters'
_journal_page_first              2742
_journal_page_last               2745
_journal_paper_doi               10.1021/ol300967a
_journal_volume                  14
_journal_year                    2012
_chemical_formula_moiety         'C27 H21 N O6'
_chemical_formula_sum            'C27 H21 N O6'
_chemical_formula_weight         455.45
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.696(12)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   42.39(2)
_cell_length_b                   13.376(6)
_cell_length_c                   7.320(3)
_cell_measurement_reflns_used    1017
_cell_measurement_temperature    123(2)
_cell_measurement_theta_max      23.36
_cell_measurement_theta_min      2.84
_cell_volume                     4150(3)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      123(2)
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'normal-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0696
_diffrn_reflns_av_sigmaI/netI    0.0927
_diffrn_reflns_limit_h_max       50
_diffrn_reflns_limit_h_min       -50
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            3783
_diffrn_reflns_theta_full        25.09
_diffrn_reflns_theta_max         25.09
_diffrn_reflns_theta_min         2.10
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.104
_exptl_absorpt_correction_T_max  0.861954
_exptl_absorpt_correction_T_min  0.668942
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'TWINABS 2008/4'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.458
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             1904
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.276
_refine_diff_density_min         -0.295
_refine_diff_density_rms         0.067
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.018
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     308
_refine_ls_number_reflns         3783
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.018
_refine_ls_R_factor_all          0.1147
_refine_ls_R_factor_gt           0.0588
_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^)+(0.0554P)^2^+0.9292P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1176
_refine_ls_wR_factor_ref         0.1443
_reflns_number_gt                2314
_reflns_number_total             3783
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol300967a_si_003.cif
_cod_data_source_block           12079t5
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_cell_volume        4151(3)
_cod_original_sg_symbol_H-M      C2/c
_cod_database_code               1507719