#------------------------------------------------------------------------------
#$Date: 2016-02-14 06:40:26 +0200 (Sun, 14 Feb 2016) $
#$Revision: 176432 $
#$URL: svn://www.crystallography.net/cod/cif/1/51/19/1511921.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_1511921
loop_
_publ_author_name
'Senczyszyn, Jemma'
'Brice, Heloise'
'Clayden, Jonathan'
_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/[σ²(Fo²)+(0.0489P)²+0.4712P] where P=(Fo²+2Fc²)/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
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z'
'-x, -y, -z'
'x, -y-1/2, z'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
S1 S 0.68839(6) 0.2500 0.70200(5) 0.01929(16) Uani 1 2 d S
F1 F 0.40994(15) 0.2500 0.68786(14) 0.0328(4) Uani 1 2 d S
F2 F 0.45913(10) 0.13648(10) 0.53372(10) 0.0313(3) Uani 1 1 d .
O1 O 0.71488(13) 0.11829(15) 0.76777(12) 0.0336(3) Uani 1 1 d .
O2 O 1.14118(17) 0.2500 0.45682(14) 0.0234(4) Uani 1 2 d S
N1 N 0.7695(2) 0.2500 0.59000(17) 0.0166(4) Uani 1 2 d S
N2 N 1.03025(19) 0.2500 0.23500(17) 0.0154(4) Uani 1 2 d S
C1 C 0.4900(2) 0.2500 0.6077(2) 0.0167(4) Uani 1 2 d S
C2 C 0.79467(16) 0.12113(16) 0.53297(14) 0.0173(3) Uani 1 1 d .
H2 H 0.7784 0.0341 0.5703 0.021 Uiso 1 1 calc R
C3 C 0.84014(16) 0.11931(16) 0.42934(14) 0.0165(3) Uani 1 1 d .
H3 H 0.8567 0.0298 0.3963 0.020 Uiso 1 1 calc R
C4 C 0.8676(2) 0.2500 0.35970(19) 0.0136(4) Uani 1 2 d S
C5 C 1.0310(2) 0.2500 0.3608(2) 0.0160(4) Uani 1 2 d S
C6 C 0.7834(2) 0.2500 0.21405(19) 0.0136(4) Uani 1 2 d S
C7 C 0.8823(2) 0.2500 0.14959(19) 0.0143(4) Uani 1 2 d S
H7 H 0.8568 0.2500 0.0573 0.017 Uiso 1 2 calc SR
C8 C 1.1695(2) 0.2500 0.2021(2) 0.0247(5) Uani 1 2 d S
H8A H 1.2280 0.1654 0.2412 0.030 Uiso 0.50 1 calc PR
H8B H 1.2280 0.3346 0.2412 0.030 Uiso 0.50 1 calc PR
C9 C 1.1464(2) 0.2500 0.0574(2) 0.0172(4) Uani 1 2 d S
C10 C 1.1378(2) 0.12482(18) -0.00984(17) 0.0305(4) Uani 1 1 d .
H10 H 1.1435 0.0374 0.0348 0.037 Uiso 1 1 calc R
C11 C 1.1209(2) 0.12514(18) -0.14196(17) 0.0314(4) Uani 1 1 d .
H11 H 1.1142 0.0378 -0.1869 0.038 Uiso 1 1 calc R
C12 C 1.1136(2) 0.2500 -0.2088(2) 0.0181(4) Uani 1 2 d S
H12 H 1.1037 0.2500 -0.2990 0.022 Uiso 1 2 calc SR
C13 C 0.6169(2) 0.2500 0.1587(2) 0.0172(4) Uani 1 2 d S
H13 H 0.579(4) 0.313(4) 0.199(4) 0.021 Uiso 0.50 1 d P
C14 C 0.5651(3) 0.2500 0.0131(3) 0.0731(15) Uani 1 2 d S
H14A H 0.5915 0.3401 -0.0188 0.110 Uiso 0.50 1 calc PR
H14B H 0.4572 0.2377 -0.0187 0.110 Uiso 0.50 1 calc PR
H14C H 0.6126 0.1721 -0.0188 0.110 Uiso 0.50 1 calc PR
C15 C 0.5515(4) 0.1038(4) 0.1794(3) 0.0284(8) Uani 0.50 1 d P
H15A H 0.4436 0.1050 0.1393 0.043 Uiso 0.50 1 calc PR
H15B H 0.5755 0.0850 0.2729 0.043 Uiso 0.50 1 calc PR
H15C H 0.5943 0.0293 0.1391 0.043 Uiso 0.50 1 calc PR
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
O1 S1 O1 123.00(12) 4_565 .
O1 S1 N1 108.82(6) 4_565 .
O1 S1 N1 108.82(6) . .
O1 S1 C1 105.58(6) 4_565 .
O1 S1 C1 105.58(6) . .
N1 S1 C1 103.21(9) . .
C2 N1 C2 118.35(17) . 4_565
C2 N1 S1 120.44(8) . .
C2 N1 S1 120.44(8) 4_565 .
C5 N2 C7 110.27(17) . .
C5 N2 C8 121.17(17) . .
C7 N2 C8 128.56(17) . .
F2 C1 F2 109.33(18) 4_565 .
F2 C1 F1 109.57(12) 4_565 .
F2 C1 F1 109.57(12) . .
F2 C1 S1 109.37(11) 4_565 .
F2 C1 S1 109.37(11) . .
F1 C1 S1 109.63(15) . .
C3 C2 N1 121.57(14) . .
C3 C2 H2 119.2 . .
N1 C2 H2 119.2 . .
C2 C3 C4 124.38(14) . .
C2 C3 H3 117.8 . .
C4 C3 H3 117.8 . .
C3 C4 C3 109.71(17) . 4_565
C3 C4 C6 113.43(11) . .
C3 C4 C6 113.43(11) 4_565 .
C3 C4 C5 108.91(11) . .
C3 C4 C5 108.91(11) 4_565 .
C6 C4 C5 102.04(15) . .
O2 C5 N2 125.9(2) . .
O2 C5 C4 126.66(18) . .
N2 C5 C4 107.47(17) . .
C7 C6 C13 128.01(19) . .
C7 C6 C4 108.18(18) . .
C13 C6 C4 123.80(17) . .
C6 C7 N2 112.04(18) . .
C6 C7 H7 124.0 . .
N2 C7 H7 124.0 . .
N2 C8 C9 113.53(17) . .
N2 C8 H8A 108.9 . .
C9 C8 H8A 108.9 . .
N2 C8 H8B 108.9 . .
C9 C8 H8B 108.9 . .
H8A C8 H8B 107.7 . .
C10 C9 C10 118.4(2) . 4_565
C10 C9 C8 120.77(10) . .
C10 C9 C8 120.77(10) 4_565 .
C9 C10 C11 120.66(16) . .
C9 C10 H10 119.7 . .
C11 C10 H10 119.7 . .
C12 C11 C10 120.92(16) . .
C12 C11 H11 119.5 . .
C10 C11 H11 119.5 . .
C11 C12 C11 118.4(2) 4_565 .
C11 C12 H12 120.8 4_565 .
C11 C12 H12 120.8 . .
C14 C13 C6 112.23(19) . .
C14 C13 C15 97.82(17) . 4_565
C6 C13 C15 111.01(15) . 4_565
C14 C13 C15 97.82(17) . .
C6 C13 C15 111.01(15) . .
C15 C13 C15 124.8(3) 4_565 .
C14 C13 H13 118(2) . .
C6 C13 H13 110(2) . .
C15 C13 H13 24(2) 4_565 .
C15 C13 H13 107(2) . .
C13 C14 H14A 109.5 . .
C13 C14 H14B 109.5 . .
H14A C14 H14B 109.5 . .
C13 C14 H14C 109.5 . .
H14A C14 H14C 109.5 . .
H14B C14 H14C 109.5 . .
C13 C15 H15A 109.5 . .
C13 C15 H15B 109.5 . .
H15A C15 H15B 109.5 . .
C13 C15 H15C 109.5 . .
H15A C15 H15C 109.5 . .
H15B C15 H15C 109.5 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
S1 O1 1.4165(13) 4_565
S1 O1 1.4165(13) .
S1 N1 1.6244(17) .
S1 C1 1.840(2) .
F1 C1 1.318(2) .
F2 C1 1.3153(15) .
O2 C5 1.222(3) .
N1 C2 1.4183(17) .
N1 C2 1.4183(17) 4_565
N2 C5 1.357(3) .
N2 C7 1.419(3) .
N2 C8 1.471(3) .
C1 F2 1.3153(15) 4_565
C2 C3 1.320(2) .
C2 H2 0.9500 .
C3 C4 1.5105(18) .
C3 H3 0.9500 .
C4 C3 1.5105(18) 4_565
C4 C6 1.527(3) .
C4 C5 1.547(3) .
C6 C7 1.332(3) .
C6 C13 1.505(3) .
C7 H7 0.9500 .
C8 C9 1.510(3) .
C8 H8A 0.9900 .
C8 H8B 0.9900 .
C9 C10 1.377(2) .
C9 C10 1.377(2) 4_565
C10 C11 1.386(2) .
C10 H10 0.9500 .
C11 C12 1.374(2) .
C11 H11 0.9500 .
C12 C11 1.374(2) 4_565
C12 H12 0.9500 .
C13 C14 1.495(3) .
C13 C15 1.560(4) 4_565
C13 C15 1.560(4) .
C13 H13 0.88(4) .
C14 H14A 0.9800 .
C14 H14B 0.9800 .
C14 H14C 0.9800 .
C15 H15A 0.9800 .
C15 H15B 0.9800 .
C15 H15C 0.9800 .
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_4
O1 S1 N1 C2 163.29(14) 4_565 .
O1 S1 N1 C2 26.90(17) . .
C1 S1 N1 C2 -84.90(14) . .
O1 S1 N1 C2 -26.91(17) 4_565 4_565
O1 S1 N1 C2 -163.29(14) . 4_565
C1 S1 N1 C2 84.90(14) . 4_565
O1 S1 C1 F2 54.32(14) 4_565 4_565
O1 S1 C1 F2 -174.02(11) . 4_565
N1 S1 C1 F2 -59.85(11) . 4_565
O1 S1 C1 F2 174.02(11) 4_565 .
O1 S1 C1 F2 -54.32(14) . .
N1 S1 C1 F2 59.85(11) . .
O1 S1 C1 F1 -65.83(6) 4_565 .
O1 S1 C1 F1 65.83(6) . .
N1 S1 C1 F1 180.0 . .
C2 N1 C2 C3 -0.1(3) 4_565 .
S1 N1 C2 C3 169.93(13) . .
N1 C2 C3 C4 -1.1(3) . .
C2 C3 C4 C3 1.9(3) . 4_565
C2 C3 C4 C6 -126.08(17) . .
C2 C3 C4 C5 121.04(16) . .
C7 N2 C5 O2 180.0 . .
C8 N2 C5 O2 0.0 . .
C7 N2 C5 C4 0.0 . .
C8 N2 C5 C4 180.0 . .
C3 C4 C5 O2 -59.81(11) . .
C3 C4 C5 O2 59.81(11) 4_565 .
C6 C4 C5 O2 180.0 . .
C3 C4 C5 N2 120.19(11) . .
C3 C4 C5 N2 -120.19(11) 4_565 .
C6 C4 C5 N2 0.0 . .
C3 C4 C6 C7 -116.98(12) . .
C3 C4 C6 C7 116.98(12) 4_565 .
C5 C4 C6 C7 0.0 . .
C3 C4 C6 C13 63.02(12) . .
C3 C4 C6 C13 -63.02(12) 4_565 .
C5 C4 C6 C13 180.0 . .
C13 C6 C7 N2 180.0 . .
C4 C6 C7 N2 0.0 . .
C5 N2 C7 C6 0.0 . .
C8 N2 C7 C6 180.0 . .
C5 N2 C8 C9 180.0 . .
C7 N2 C8 C9 0.0 . .
N2 C8 C9 C10 -90.94(18) . .
N2 C8 C9 C10 90.94(18) . 4_565
C10 C9 C10 C11 0.0(3) 4_565 .
C8 C9 C10 C11 -178.13(19) . .
C9 C10 C11 C12 0.5(3) . .
C10 C11 C12 C11 -1.1(4) . 4_565
C7 C6 C13 C14 0.0 . .
C4 C6 C13 C14 180.0 . .
C7 C6 C13 C15 -108.3(2) . 4_565
C4 C6 C13 C15 71.7(2) . 4_565
C7 C6 C13 C15 108.3(2) . .
C4 C6 C13 C15 -71.7(2) . .
