A Chemoenzymatic Total Synthesis of (+)-Clividine
Lorenzo V. White; Brett D. Schwartz; Martin G. Banwell; Anthony C. Willis; Journal of Organic Chemistry 76 (2011) 6250–6257; doi:10.1021/jo201005d

data_4026493
_publ_contact_author_address
;
Research School of Chemistry,
Australian National University,
Canberra, ACT 0200, Australia
;
_publ_contact_author_email       ' mgb@rsc.anu.edu.au '
_publ_contact_author_fax         ' 61 2 6125 8114 '
_publ_contact_author_name        'Martin G. Banwell'
_publ_contact_author_phone       ' 61 2 6125 8202 '
_publ_section_title
;
 A Chemoenzymatic Total Synthesis of (+)-Clividine
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              6250
_journal_page_last               6257
_journal_paper_doi               10.1021/jo201005d
_journal_volume                  76
_journal_year                    2011
_chemical_absolute_configuration syn
_chemical_compound_source        local
_chemical_formula_moiety
'C17 H20 N O5 +, C6 H2 N3 O7 -, 3.93 (H2 O), 0.157 (C2 H3 N)'
_chemical_formula_sum            'C23.315 H30.345 N4.157 O15.93'
_chemical_formula_weight         623.8
_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             11-01-25
_audit_creation_method           CRYSTALS_ver_14.11
_audit_update_record
;
2011-01-25 - Report on C23.31 H27 N4.16 O15.94 
             by Anthony C. Willis
             for   Lorenzo White and Martin Banwell

2011-01-27 - passes checkcif tests with few warnings about missing H 
;
_cell_angle_alpha                90
_cell_angle_beta                 101.1071(12)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.6590(2)
_cell_length_b                   35.4747(9)
_cell_length_c                   9.0925(2)
_cell_measurement_reflns_used    79503
_cell_measurement_temperature    200
_cell_measurement_theta_max      25
_cell_measurement_theta_min      2.6
_cell_volume                     2740.68(11)
_computing_cell_refinement       'DENZO/SCALEPACK (Otwinowski & Minor, 1997)'
_computing_data_collection       'COLLECT (Nonius, 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       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  0.059
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       42
_diffrn_reflns_limit_k_min       -41
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            36492
_diffrn_reflns_theta_full        25.058
_diffrn_reflns_theta_max         25.058
_diffrn_reflns_theta_min         2.555
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.129
_exptl_absorpt_correction_T_max  1.00
_exptl_absorpt_correction_T_min  0.82
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'DENZO/SCALEPACK (Otwinowski & Minor, 1997)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.512
_exptl_crystal_description       lath
_exptl_crystal_F_000             1307.3
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.080
_exptl_crystal_size_min          0.030
_refine_diff_density_max         0.38
_refine_diff_density_min         -0.46
_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   1.0230
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     797
_refine_ls_number_reflns         4932
_refine_ls_number_restraints     5
_refine_ls_R_factor_all          0.0704
_refine_ls_R_factor_gt           0.0504
_refine_ls_shift/su_max          0.0325819
_refine_ls_shift/su_mean         0.0023869
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
 Method= Modified Sheldrick 
 w=1/[\s^2^(F^2^) + ( 0.03P)^2^ + 2.76P] 
 ,where P=(max(Fo^2^,0) + 2Fc^2^)/3 
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.1098
_refine_ls_wR_factor_gt          0.1006
_refine_ls_wR_factor_ref         0.1098
_reflns_limit_h_max              10
_reflns_limit_h_min              -10
_reflns_limit_k_max              42
_reflns_limit_k_min              0
_reflns_limit_l_max              10
_reflns_limit_l_min              0
_reflns_number_gt                3901
_reflns_number_total             4933
_reflns_threshold_expression     I>2.0\s(I)
_oxford_diffrn_Wilson_B_factor   3.09
_oxford_diffrn_Wilson_scale      12.84
_oxford_refine_ls_r_factor_ref   0.0704
_oxford_refine_ls_scale          0.3108(3)
_oxford_reflns_number_all        4932
_oxford_reflns_threshold_expression_ref I>-10.0\s(I)
_oxford_structure_analysis_title '1241423 ban105B'
_cod_data_source_file            jo201005d_si_003.cif
_cod_data_source_block           ban1105B
_cod_depositor_comments
;

2025-10-08
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_sum            'C46.63 H60.69 N8.315 O31.87'
_cod_original_formula_weight         1247.6
_cod_original_formula_moiety
;
2(C17 H20 N O5 +), 2(C6 H2 N3 O7 -), 7.87 H2 O, 0.315 C2 H3 N
;
_cod_original_formula_units_Z            2
_cod_original_sg_symbol_H-M      'P 1 21 1 '
_cod_database_code               4026493