First total synthesis of (+/-)-3-hydroxy-11-norcytisine: structure confirmation and biological characterization.
Yohannes, Daniel; Hansen, Camilla P.; Akireddy, Srinivasa Rao; Hauser, Terry A.; Kiser, Melanie N.; Gurnon, Nicholas J.; Day, Cynthia S.; Bhatti, Balwinder; Caldwell, William S.; Organic letters 10 (2008) 5353–5356; doi:10.1021/ol802145b

data_1504944
_publ_section_title
;
 First total synthesis of (+/-)-3-hydroxy-11-norcytisine: structure
 confirmation and biological characterization.
;
_journal_issue                   23
_journal_name_full               'Organic letters'
_journal_page_first              5353
_journal_page_last               5356
_journal_paper_doi               10.1021/ol802145b
_journal_volume                  10
_journal_year                    2008
_chemical_formula_sum            'C34 H34 N4 O6 S2'
_chemical_formula_weight         658.77
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXTL-PC
_cell_angle_alpha                90.00
_cell_angle_beta                 96.409(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   6.9334(15)
_cell_length_b                   22.473(5)
_cell_length_c                   20.118(4)
_cell_measurement_reflns_used    2301
_cell_measurement_temperature    193(2)
_cell_measurement_theta_max      20.825
_cell_measurement_theta_min      3.813
_cell_volume                     3115.1(11)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'Bruker SHELXTL'
_computing_structure_solution    'Bruker SHELXTL'
_diffrn_ambient_temperature      193(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker APEX CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0712
_diffrn_reflns_av_sigmaI/netI    0.0668
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       28
_diffrn_reflns_limit_k_min       -28
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            25160
_diffrn_reflns_theta_full        26.37
_diffrn_reflns_theta_max         26.37
_diffrn_reflns_theta_min         3.85
_exptl_absorpt_coefficient_mu    0.225
_exptl_absorpt_correction_T_max  0.9911
_exptl_absorpt_correction_T_min  0.9377
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
 Data were processed with the Bruker AXS area detector scaling
 and absorption correction (SADABS).  
;
_exptl_crystal_colour            'pale yellow'
_exptl_crystal_density_diffrn    1.405
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             1384
_exptl_crystal_size_max          0.29
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.403
_refine_diff_density_min         -0.298
_refine_diff_density_rms         0.058
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     441
_refine_ls_number_reflns         6348
_refine_ls_number_restraints     6
_refine_ls_restrained_S_all      1.028
_refine_ls_R_factor_all          0.0972
_refine_ls_R_factor_gt           0.0576
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0681P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1237
_refine_ls_wR_factor_ref         0.1404
_reflns_number_gt                4191
_reflns_number_total             6348
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol802145b_si_002.cif
_cod_data_source_block           a70m2t
_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_cell_volume        3115.1(12)
_cod_original_sg_symbol_H-M      P2(1)/n
_cod_database_code               1504944