Spirocyclic dihydropyridines by electrophile-induced dearomatizing cyclization of N-alkenyl pyridinecarboxamides.
Senczyszyn, Jemma; Brice, Heloise; Clayden, Jonathan; Organic letters 15 (2013) 1922–1925; doi:10.1021/ol400571j

data_1511921
_publ_contact_author
; 
    Madeleine Helliwell 
;
_publ_section_title
;
 Spirocyclic dihydropyridines by electrophile-induced dearomatizing
 cyclization of N-alkenyl pyridinecarboxamides.
;
_journal_issue                   8
_journal_name_full               'Organic letters'
_journal_page_first              1922
_journal_page_last               1925
_journal_paper_doi               10.1021/ol400571j
_journal_volume                  15
_journal_year                    2013
_chemical_formula_moiety         'C19 H19 F3 N2 O3 S'
_chemical_formula_sum            'C19 H19 F3 N2 O3 S'
_chemical_formula_weight         412.42
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           11
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yb'
_symmetry_space_group_name_H-M   'P 1 21/m 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 108.172(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   9.4896(15)
_cell_length_b                   9.4513(14)
_cell_length_c                   10.8050(16)
_cell_measurement_reflns_used    1022
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      26.29
_cell_measurement_theta_min      2.93
_cell_volume                     920.8(2)
_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  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  '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  0.0291
_diffrn_reflns_av_sigmaI/netI    0.0264
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            5349
_diffrn_reflns_theta_full        26.39
_diffrn_reflns_theta_max         26.39
_diffrn_reflns_theta_min         1.98
_exptl_absorpt_coefficient_mu    0.229
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.488
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             428
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.30
_refine_diff_density_max         0.490
_refine_diff_density_min         -0.348
_refine_diff_density_rms         0.056
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     159
_refine_ls_number_reflns         1990
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.059
_refine_ls_R_factor_all          0.0415
_refine_ls_R_factor_gt           0.0375
_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^)+(0.0489P)^2^+0.4712P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0947
_refine_ls_wR_factor_ref         0.0975
_reflns_number_gt                1815
_reflns_number_total             1990
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol400571j_si_002.cif
_cod_data_source_block           s3623twm
_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 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 1891 2012-01-12 08:04:46Z andrius 
;
_cod_original_sg_symbol_Hall     -P2yb
_cod_original_sg_symbol_H-M      P2(1)/m
_cod_database_code               1511921