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_4026494
_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 ad
_chemical_compound_source        local
_chemical_formula_moiety         'C11 H14 Br N O3'
_chemical_formula_sum            'C11 H14 Br N O3'
_chemical_formula_weight         288.14
_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             10-05-11
_audit_creation_method           CRYSTALS_ver_12.87
_audit_update_record
;
2010-05-11 - Report on C11 H14 Br N O3 
             by Anthony C. Willis
             for   Lorenzo White and Martin Banwell

2010-05-11 - passes checkcif tests with no warnings  
;
_cell_angle_alpha                90
_cell_angle_beta                 113.6267(15)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   10.0349(3)
_cell_length_b                   5.8790(1)
_cell_length_c                   11.4499(3)
_cell_measurement_reflns_used    14765
_cell_measurement_temperature    200
_cell_measurement_theta_max      27.5
_cell_measurement_theta_min      2.6
_cell_volume                     618.87(3)
_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 0.993
_diffrn_measured_fraction_theta_max 0.992
_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  0.080
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            12645
_diffrn_reflns_theta_full        26.943
_diffrn_reflns_theta_max         27.493
_diffrn_reflns_theta_min         3.483
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    3.313
_exptl_absorpt_correction_T_max  0.714
_exptl_absorpt_correction_T_min  0.319
_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    1.546
_exptl_crystal_description       block
_exptl_crystal_F_000             292
_exptl_crystal_size_max          0.590
_exptl_crystal_size_mid          0.170
_exptl_crystal_size_min          0.120
_refine_diff_density_max         0.64
_refine_diff_density_min         -0.56
_refine_ls_abs_structure_details 'Flack (1983), 1157 Friedel-pairs'
_refine_ls_abs_structure_Flack   -0.015(7)
_refine_ls_extinction_coef       151(14)
_refine_ls_extinction_method     'Larson (1970), Equation 22'
_refine_ls_goodness_of_fit_ref   1.0093
_refine_ls_hydrogen_treatment    refxyz
_refine_ls_matrix_type           full
_refine_ls_number_parameters     189
_refine_ls_number_reflns         2718
_refine_ls_number_restraints     50
_refine_ls_R_factor_all          0.0261
_refine_ls_R_factor_gt           0.0249
_refine_ls_shift/su_max          0.0030844
_refine_ls_shift/su_mean         0.0005
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
 Method= Modified Sheldrick 
 w=1/[\s^2^(F^2^) + ( 0.04P)^2^ + 0.11P] 
 ,where P=(max(Fo^2^,0) + 2Fc^2^)/3 
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.0651
_refine_ls_wR_factor_gt          0.0641
_refine_ls_wR_factor_ref         0.0651
_reflns_limit_h_max              11
_reflns_limit_h_min              -13
_reflns_limit_k_max              7
_reflns_limit_k_min              -6
_reflns_limit_l_max              14
_reflns_limit_l_min              0
_reflns_number_gt                2619
_reflns_number_total             2718
_reflns_threshold_expression     I>2.0\s(I)
_oxford_diffrn_Wilson_B_factor   3.49
_oxford_diffrn_Wilson_scale      0.11
_oxford_refine_ls_r_factor_ref   0.0261
_oxford_refine_ls_scale          3.22(4)
_oxford_reflns_number_all        2718
_oxford_reflns_threshold_expression_ref I>-10.0\s(I)
_oxford_structure_analysis_title '5111245 ban1014'
_cod_data_source_file            jo201005d_si_004.cif
_cod_data_source_block           ban1014
_cod_original_sg_symbol_H-M      'P 1 21 1 '
_cod_database_code               4026494