Synthesis of C-4 substituted nicotine derivatives via an N-acylpyridinium salt of (S)-nicotine.
Comins, Daniel L.; King, Laura S.; Smith, Emilie D.; Février, Florence C; Organic letters 7 (2005) 5059–5062; doi:10.1021/ol0520469

data_1506738
_publ_section_title
;
 Synthesis of C-4 substituted nicotine derivatives via an N-acylpyridinium
 salt of (S)-nicotine.
;
_journal_issue                   22
_journal_name_full               'Organic letters'
_journal_page_first              5059
_journal_page_last               5062
_journal_paper_doi               10.1021/ol0520469
_journal_volume                  7
_journal_year                    2005
_chemical_formula_moiety         'C21 H28 N2 O '
_chemical_formula_sum            'C21 H28 N2 O'
_chemical_formula_weight         324.46
_chemical_melting_point_gt       357
_chemical_melting_point_lt       358
_chemical_name_systematic
;
1-[(4R)-3-((2S)-1-methylpyrrolidin-2-yl)-4-phenyl-(1,4-dihydropyridyl)]-2,2-dimethylpropan-1-one    
;
_space_group_IT_number           19
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_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
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_cell_angle_beta                 90.0
_cell_angle_gamma                90.0
_cell_formula_units_Z            4
_cell_length_a                   10.3478(5)
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_cell_length_c                   18.2446(12)
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_cell_measurement_temperature    148
_cell_measurement_theta_max      19.00
_cell_measurement_theta_min      17.50
_cell_volume                     1848.68(18)
_computing_cell_refinement       'Nonius CAD4 Argus'
_computing_data_collection       'Nonius CAD4 Argus'
_computing_data_reduction        'NRCVAX DATRD2'
_computing_molecular_graphics    NRCVAX
_computing_publication_material  'NRCVAX TABLES Jan 94 Version'
_computing_structure_refinement  'NRCVAX LSTSQ'
_computing_structure_solution    SIR92
_diffrn_ambient_temperature      148
_diffrn_measurement_device       'Nonius CAD-4    '
_diffrn_measurement_method       'Omega scan b/P/b        '
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'xray tube'
_diffrn_radiation_type           'Molybdenum K\a'
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_diffrn_reflns_limit_h_min       0
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_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       0
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_diffrn_reflns_theta_min         1.20
_diffrn_standards_decay_%        2.0
_diffrn_standards_interval_time  80
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    .07
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
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_exptl_crystal_description       'cut prism'
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_exptl_crystal_size_mid          .34
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_refine_ls_extinction_method     Larson
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_refine_ls_hydrogen_treatment    refall
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_refine_ls_R_factor_all          .029
_refine_ls_R_factor_obs          .029
_refine_ls_shift/esd_max         .001
_refine_ls_structure_factor_coef F
_refine_ls_weighting_details     '1/(\s^2^(F)+ .0003F^2^) '
_refine_ls_weighting_scheme      sigma
_refine_ls_wR_factor_all         .033
_refine_ls_wR_factor_obs         .033
_reflns_number_observed          2940
_reflns_number_total             3218
_reflns_observed_criterion       'Inet > 1.0\s(Inet)'
_cod_data_source_file            ol0520469si20050824_111537.cif
_cod_data_source_block           10b
_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_formula_sum        'C21 H28 N2 O '
_cod_database_code               1506738