A chemoenzymatic total synthesis of the structure assigned to the alkaloid (+)-montabuphine.
Matveenko, Maria; Banwell, Martin G.; Willis, Anthony C.; Organic letters 10 (2008) 4693–4696; doi:10.1021/ol801815k

data_1504896
_publ_section_title
;
 A chemoenzymatic total synthesis of the structure assigned to the
 alkaloid (+)-montabuphine.
;
_journal_issue                   20
_journal_name_full               'Organic letters'
_journal_page_first              4693
_journal_page_last               4696
_journal_paper_doi               10.1021/ol801815k
_journal_volume                  10
_journal_year                    2008
_chemical_absolute_configuration syn
_chemical_compound_source        local
_chemical_formula_moiety         'C17 H20 N O4 +, C2 H O4 -, 0.09(H2 O)'
_chemical_formula_sum            'C19 H21.18 N O8.09'
_chemical_formula_weight         392.95
_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
_audit_creation_date             08-08-18
_audit_creation_method           CRYSTALS_ver_12.85
_audit_update_record
;
2008-08-18 - Report on C19 H21.18 N1 O8.09
             by Anthony C. Willis
             for   Maria Matveenko and Martin Banwell

2008-08-18 - passes checkcif tests with minor warnings  
;
_cell_angle_alpha                90
_cell_angle_beta                 92.8111(12)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.54860(10)
_cell_length_b                   16.0954(3)
_cell_length_c                   12.7901(2)
_cell_measurement_reflns_used    38429
_cell_measurement_temperature    200
_cell_measurement_theta_max      27.5
_cell_measurement_theta_min      2.6
_cell_volume                     1757.71(5)
_computing_cell_refinement       'DENZO/SCALEPACK (Otwinowski & Minor, 1997)'
_computing_data_collection       'COLLECT (Nonius, 1997-2001).'
_computing_data_reduction        'DENZO/SCALEPACK (Otwinowski & Minor, 1997)'
_computing_molecular_graphics
; 
ORTEP-II (Johnson 1976) in teXsan (MSC, 1992-1997)
;
_computing_publication_material  'CRYSTALS (Betteridge et al., 2003)'
_computing_structure_refinement  'CRYSTALS (Betteridge et al., 2003)'
_computing_structure_solution    'SIR92 (Altomare et al., 1994)'
_diffrn_ambient_temperature      200
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device       'Nonius KappaCCD'
_diffrn_measurement_device_type  Area
_diffrn_measurement_method       ' \f and \w scans with CCD '
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.039
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            37573
_diffrn_reflns_theta_full        27.478
_diffrn_reflns_theta_max         27.478
_diffrn_reflns_theta_min         2.700
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.117
_exptl_absorpt_correction_T_max  0.987
_exptl_absorpt_correction_T_min  0.954
_exptl_absorpt_correction_type   integration
_exptl_absorpt_process_details
;
via Gaussian method (Coppens, 1970) implemented in maXus (2000)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.484
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             826.773
_exptl_crystal_size_max          0.46
_exptl_crystal_size_mid          0.45
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.19
_refine_diff_density_min         -0.16
_refine_ls_abs_structure_details
;
The enantiomer has been assigned by reference to an unchanging chiral
centre in the synthetic procedure.
;
_refine_ls_extinction_method     None
_refine_ls_goodness_of_fit_ref   0.9413
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     533
_refine_ls_number_reflns         4159
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0293
_refine_ls_R_factor_gt           0.0265
_refine_ls_shift/su_max          0.022422
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
 Method= Modified Sheldrick 
 w=1/[\s^2^(F^2^) + ( 0.04P)^2^ + 0.00P] 
 ,where P=(max(Fo^2^,0) + 2Fc^2^)/3 
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.0675
_refine_ls_wR_factor_gt          0.0663
_refine_ls_wR_factor_ref         0.0675
_reflns_limit_h_max              11
_reflns_limit_h_min              -11
_reflns_limit_k_max              20
_reflns_limit_k_min              0
_reflns_limit_l_max              16
_reflns_limit_l_min              0
_reflns_number_gt                3826
_reflns_number_total             4160
_reflns_threshold_expression     I>2.0\s(I)
_oxford_diffrn_Wilson_B_factor   2.53
_oxford_diffrn_Wilson_scale      0.71
_oxford_refine_ls_r_factor_ref   0.0293
_oxford_refine_ls_scale          1.205(4)
_oxford_reflns_number_all        4159
_oxford_reflns_threshold_expression_ref I>-10.0\s(I)
_oxford_structure_analysis_title '8181104 ban0821'
_cod_data_source_file            ol801815k_si_002.cif
_cod_data_source_block           ban0821
_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_sg_symbol_H-M      'P 1 21 1 '
_cod_database_code               1504896