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_1504895
_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 H19 N O4'
_chemical_formula_sum            'C17 H19 N O4'
_chemical_formula_weight         301.34
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_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             08-06-05
_audit_creation_method           CRYSTALS_ver_12.85
_audit_update_record
;
2008-06-05 - Report on C17 H19 N O4
             by Anthony C. Willis
             for   Maria Matveenko and Martin Banwell

2008-06-05 - passes checkcif tests with minor warnings  
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.5581(6)
_cell_length_b                   10.9515(8)
_cell_length_c                   12.6633(8)
_cell_measurement_reflns_used    17341
_cell_measurement_temperature    200
_cell_measurement_theta_max      25
_cell_measurement_theta_min      2.6
_cell_volume                     1464.22(16)
_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 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device       Area
_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
_diffrn_reflns_av_R_equivalents  0.073
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            10548
_diffrn_reflns_theta_full        25.025
_diffrn_reflns_theta_max         25.025
_diffrn_reflns_theta_min         2.680
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.098
_exptl_absorpt_correction_T_max  0.996
_exptl_absorpt_correction_T_min  0.821
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
multi-scan from symmetry-related measurements 
 Sortav (Blessing 1995, 1997)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.367
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             640
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.24
_refine_diff_density_min         -0.21
_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   0.8184
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     202
_refine_ls_number_reflns         1485
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0486
_refine_ls_R_factor_gt           0.0328
_refine_ls_shift/su_max          0.000258
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
 Method= Modified Sheldrick 
 w=1/[\s^2^(F^2^) + ( 0.02P)^2^ + 0.00P] 
 ,where P=(max(Fo^2^,0) + 2Fc^2^)/3 
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.0672
_refine_ls_wR_factor_gt          0.0635
_refine_ls_wR_factor_ref         0.0672
_reflns_limit_h_max              12
_reflns_limit_h_min              0
_reflns_limit_k_max              13
_reflns_limit_k_min              0
_reflns_limit_l_max              15
_reflns_limit_l_min              0
_reflns_number_gt                1139
_reflns_number_total             1493
_reflns_threshold_expression     I>2.0\s(I)
_oxford_diffrn_Wilson_B_factor   2.81
_oxford_diffrn_Wilson_scale      1.87
_oxford_refine_ls_r_factor_ref   0.0486
_oxford_refine_ls_scale          0.733(2)
_oxford_reflns_number_all        1485
_oxford_reflns_threshold_expression_ref I>-10.0\s(I)
_oxford_structure_analysis_title '6051459 ban0813'
_cod_data_source_file            ol801815k_si_002.cif
_cod_data_source_block           ban0813
_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 
;
_cod_original_sg_symbol_H-M      'P 21 21 21 '
_cod_database_code               1504895