Organocatalytic enantioselective Michael-Michael-Michael-aldol condensation reactions: control of five stereocenters in a quadruple-cascade asymmetric synthesis of highly functionalized hexahydrophenanthrenes.
Raja, Arun; Hong, Bor-Cherng; Lee, Gene-Hsiang; Organic letters 16 (2014) 5756–5759; doi:10.1021/ol502821e

data_1518109
_publ_section_title
;
 Organocatalytic enantioselective Michael-Michael-Michael-aldol
 condensation reactions: control of five stereocenters in a
 quadruple-cascade asymmetric synthesis of highly functionalized
 hexahydrophenanthrenes.
;
_journal_issue                   21
_journal_name_full               'Organic letters'
_journal_page_first              5756
_journal_page_last               5759
_journal_paper_doi               10.1021/ol502821e
_journal_volume                  16
_journal_year                    2014
_chemical_absolute_configuration ad
_chemical_formula_sum            'C34 H25 Cl2 N3 O8'
_chemical_formula_weight         674.47
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_cell_volume                     3032.06(11)
_computing_cell_refinement       DENZO-SMN
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_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      200(2)
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_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'NONIUS KappaCCD'
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_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
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_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            18597
_diffrn_reflns_theta_full        27.50
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_exptl_absorpt_coefficient_mu    0.275
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_exptl_absorpt_correction_T_min  0.8864
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SORTAV (Blessing, 1995)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.478
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1392
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_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.03(4)
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_refine_ls_number_reflns         6940
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_refine_ls_R_factor_all          0.0639
_refine_ls_R_factor_gt           0.0374
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0421P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0782
_refine_ls_wR_factor_ref         0.0853
_reflns_number_gt                5016
_reflns_number_total             6940
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol502821e_si_002.cif
_cod_data_source_block           ic16882
_cod_depositor_comments
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The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Orthorhombic' changed to
'orthorhombic' according to
/home/saulius/struct/COD-crude-data--automatic-downloads/rss-feeds/ACS/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 2827 2014-09-09 07:05:25Z andrius 

 Adding full bibliography for 1518109.cif.
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_cod_original_sg_symbol_H-M      P2(1)2(1)2(1)
_cod_database_code               1518109