Formal synthesis of (-)-podophyllotoxin through the photocyclization of an axially chiral 3,4-bisbenzylidene succinate amide ester - a flow photochemistry approach.
Lisiecki, Kamil; Krawczyk, Krzysztof K.; Roszkowski, Piotr; Maurin, Jan K.; Czarnocki, Zbigniew; Organic & biomolecular chemistry 14 (2015) 460–469; doi:10.1039/c5ob01844g

data_7154793
_publ_section_title
;
 Formal synthesis of (-)-podophyllotoxin through the photocyclization of
 an axially chiral 3,4-bisbenzylidene succinate amide ester - a flow
 photochemistry approach.
;
_journal_issue                   2
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              460
_journal_page_last               469
_journal_paper_doi               10.1039/c5ob01844g
_journal_volume                  14
_journal_year                    2015
_chemical_formula_sum            'C35 H34 Br N O10'
_chemical_formula_weight         708.54
_chemical_melting_point          455
_chemical_name_systematic
'Monomethyl (S)-pyrrolidin-2-ylmethyl 3-bromobenzoate-(1R,2R)-1-(3,4,5-trimethoxyphenyl)-6,7-methylenedioxy-1,2-dihydronaphthalene-2,3-dicarboxylate amide ester'
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_audit_update_record
;
2015-07-30 deposited with the CCDC.
2015-10-27 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 98.692(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   9.1914(2)
_cell_length_b                   17.0779(3)
_cell_length_c                   10.56690(20)
_cell_measurement_reflns_used    4348
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      62.2980
_cell_measurement_theta_min      4.2200
_cell_volume                     1639.63(6)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
;
_computing_molecular_graphics    'XP, (Bruker-AXS, 2002)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.4922
_diffrn_detector_type            Ruby
_diffrn_measured_fraction_theta_full 0.969
_diffrn_measured_fraction_theta_max 0.969
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Ruby'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Enhance (Cu) X-ray Source'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0441
_diffrn_reflns_av_sigmaI/netI    0.0470
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            16482
_diffrn_reflns_theta_full        71.20
_diffrn_reflns_theta_max         71.20
_diffrn_reflns_theta_min         4.23
_exptl_absorpt_coefficient_mu    2.218
_exptl_absorpt_correction_T_max  0.957
_exptl_absorpt_correction_T_min  0.679
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
Analytical numeric absorption correction using a multifaceted crystal
            model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.435
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       parallelepiped
_exptl_crystal_F_000             732
_exptl_crystal_size_max          0.2908
_exptl_crystal_size_mid          0.1127
_exptl_crystal_size_min          0.0200
_refine_diff_density_max         0.682
_refine_diff_density_min         -0.502
_refine_diff_density_rms         0.047
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.02(3)
_refine_ls_extinction_coef       0.0011(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     425
_refine_ls_number_reflns         5620
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.032
_refine_ls_R_factor_all          0.0822
_refine_ls_R_factor_gt           0.0590
_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^)+(0.0758P)^2^+0.5931P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1468
_refine_ls_wR_factor_ref         0.1643
_reflns_number_gt                4021
_reflns_number_total             5620
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c5ob01844g2.cif
_cod_data_source_block           zc242abs
_cod_depositor_comments          'Adding full bibliography for 7154793.cif.'
_cod_original_cell_volume        1639.64(6)
_cod_database_code               7154793