Chemoenzymatic approaches to lycorine-type Amaryllidaceae alkaloids: total syntheses of ent-lycoricidine, 3-epi-ent-lycoricidine, and 4-deoxy-3-epi-ent-lycoricidine.
Matveenko, Maria; Kokas, Okanya J.; Banwell, Martin G.; Willis, Anthony C.; Organic letters 9 (2007) 3683–3685; doi:10.1021/ol701552r

data_1505520
_publ_section_title
;
 Chemoenzymatic approaches to lycorine-type Amaryllidaceae alkaloids:
 total syntheses of ent-lycoricidine, 3-epi-ent-lycoricidine, and
 4-deoxy-3-epi-ent-lycoricidine.
;
_journal_issue                   18
_journal_name_full               'Organic letters'
_journal_page_first              3683
_journal_page_last               3685
_journal_paper_doi               10.1021/ol701552r
_journal_volume                  9
_journal_year                    2007
_chemical_absolute_configuration syn
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_chemical_formula_moiety         'C20 H19 N O9'
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_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             07-03-29
_audit_creation_method           CRYSTALS_ver_12.18
_audit_update_record
;
2007-03-29 - Report on C20 H19 N O9
              by Anthony C. Willis
              for   Maria Matveenko and Martin Banwell

2007-03-29 - passes checkcif tests with some warnings
2007-04-23 - texsan stuff added

;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.0014(1)
_cell_length_b                   8.2641(2)
_cell_length_c                   28.8922(6)
_cell_measurement_reflns_used    23127
_cell_measurement_temperature    200
_cell_measurement_theta_max      27.5
_cell_measurement_theta_min      2.8
_cell_volume                     1910.48(7)
_computing_cell_refinement       'Denzo/Scalepack (Otwinowski & Minor, 1997)'
_computing_data_collection       'COLLECT (Nonius BV, 1997)'
_computing_data_reduction        'Denzo/Scalepack (Otwinowski & Minor, 1997)'
_computing_molecular_graphics
;
ORTEP-II (Johnson 1976) in teXsan (MSC, 1992-1997)
;
_computing_publication_material  'CRYSTALS (Watkin et al 2003)'
_computing_structure_refinement  'CRYSTALS (Watkin et al 2003)'
_computing_structure_solution    'SIR92 (Altomare et al, 1994)'
_diffrn_ambient_temperature      200
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Nonius KappaCCD'
_diffrn_measurement_method       ' \f and \w scans with CCD '
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
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_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
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_diffrn_reflns_limit_l_min       -22
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_diffrn_reflns_theta_max         27.482
_diffrn_reflns_theta_min         2.563
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_exptl_absorpt_process_details
;
via Gaussian method (Coppens, 1970) implemented in maXus (2000)
;
_exptl_crystal_colour            colourless
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_exptl_crystal_density_meas      ?
_exptl_crystal_description       needle
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_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.07
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_refine_diff_density_min         -0.14
_refine_ls_extinction_method     None
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_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
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_refine_ls_number_restraints     12
_refine_ls_R_factor_all          0.0428
_refine_ls_R_factor_gt           0.0290
_refine_ls_shift/su_max          0.004201
_refine_ls_structure_factor_coef F
_refine_ls_weighting_details
;
  Method, part 1, Chebychev polynomial,
(Carruthers & Watkin, 1979, Prince, 1982)
  [weight] = 1.0/[A~0~*T~0~(x)+A~1~*T~1~(x) ... +A~n-1~]*T~n-1~(x)]
  where A~i~ are the Chebychev coefficients listed below and x= Fcalc/Fmax
  Method = Robust Weighting (Prince, 1982)
  W = [weight] * [1-(deltaF/6*sigmaF)^2^]^2^
  A~i~ are:
  0.963 0.518 0.752
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.0389
_refine_ls_wR_factor_gt          0.0339
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_reflns_limit_h_max              10
_reflns_limit_h_min              0
_reflns_limit_k_max              10
_reflns_limit_k_min              0
_reflns_limit_l_max              37
_reflns_limit_l_min              0
_reflns_number_gt                1904
_reflns_number_total             2526
_reflns_threshold_expression     I>2.0\s(I)
_oxford_diffrn_Wilson_B_factor   2.85
_oxford_diffrn_Wilson_scale      2.23
_oxford_refine_ls_scale          0.6840(14)
_oxford_structure_analysis_title '3281229 ban0718'
_cod_data_source_file            ol701552r-file004.cif
_cod_data_source_block           ban0718
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Orthorhombic' changed to
'orthorhombic' 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 

The following automatic conversions were performed:

'_exptl_crystal_density_meas' value 'not measured' was changed to '?'
- the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas 
;
_cod_original_sg_symbol_H-M      'P 21 21 21 '
_cod_database_code               1505520