#------------------------------------------------------------------------------
#$Date: 2016-02-14 06:40:26 +0200 (Sun, 14 Feb 2016) $
#$Revision: 176432 $
#$URL: svn://www.crystallography.net/cod/cif/4/11/93/4119341.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_4119341
loop_
_publ_author_name
'Takahiro Nishimura'
'Yusuke Ebe'
'Tamio Hayashi'
_publ_section_title
;
 Iridium-Catalyzed [3 + 2] Annulation of Cyclic N-Sulfonyl Ketimines with
 1,3-Dienes via C-H Activation
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              2092
_journal_page_last               2095
_journal_paper_doi               10.1021/ja311968d
_journal_volume                  135
_journal_year                    2013
_chemical_formula_sum            'C20 H18 F3 N O2 S'
_chemical_formula_weight         393.41
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      14
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 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                 113.1756(8)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   12.5101(2)
_cell_length_b                   10.6780(2)
_cell_length_c                   14.8831(3)
_cell_measurement_reflns_used    9561
_cell_measurement_temperature    93(2)
_cell_measurement_theta_max      78.21
_cell_measurement_theta_min      3.23
_cell_volume                     1827.69(6)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      93(2)
_diffrn_detector_area_resol_mean 10.0
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Rigaku RAXIS-RAPID'
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54187
_diffrn_reflns_av_R_equivalents  0.0459
_diffrn_reflns_av_sigmaI/netI    0.0367
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            18084
_diffrn_reflns_theta_full        68.21
_diffrn_reflns_theta_max         68.21
_diffrn_reflns_theta_min         3.84
_exptl_absorpt_coefficient_mu    1.982
_exptl_absorpt_correction_T_max  0.8265
_exptl_absorpt_correction_T_min  0.6927
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;Higashi, T. (1995). 
 Program for Absorption Correction.
 Rigaku Corporation, Tokyo, Japan.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.430
_exptl_crystal_description       prism
_exptl_crystal_F_000             816
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.477
_refine_diff_density_min         -0.568
_refine_diff_density_rms         0.064
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.094
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     246
_refine_ls_number_reflns         3331
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.094
_refine_ls_R_factor_all          0.0574
_refine_ls_R_factor_gt           0.0436
_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)+(0.0403P)²+1.9301P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1021
_refine_ls_wR_factor_ref         0.1140
_reflns_number_gt                2658
_reflns_number_total             3331
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja311968d_si_004.cif
_cod_data_source_block           3fq
_cod_original_sg_symbol_Hall     '-p 2ybc'
_cod_database_code               4119341
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
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
C1 C -0.1485(2) 0.1159(2) 0.25498(17) 0.0211(5) Uani 1 1 d .
C2 C -0.05945(19) 0.1543(2) 0.22818(17) 0.0207(5) Uani 1 1 d .
C3 C -0.0867(2) 0.2185(2) 0.14089(17) 0.0233(5) Uani 1 1 d .
H2 H -0.0272 0.2453 0.1206 0.028 Uiso 1 1 calc R
C4 C -0.2030(2) 0.2427(2) 0.08373(18) 0.0255(5) Uani 1 1 d .
H3 H -0.2230 0.2857 0.0234 0.031 Uiso 1 1 calc R
C5 C -0.2908(2) 0.2053(2) 0.11321(18) 0.0263(5) Uani 1 1 d .
H4 H -0.3695 0.2241 0.0733 0.032 Uiso 1 1 calc R
C6 C -0.2648(2) 0.1413(2) 0.19946(17) 0.0235(5) Uani 1 1 d .
H5 H -0.3241 0.1154 0.2202 0.028 Uiso 1 1 calc R
C7 C 0.06126(19) 0.1217(2) 0.30209(17) 0.0206(5) Uani 1 1 d .
C8 C 0.13160(19) 0.2389(2) 0.35446(18) 0.0230(5) Uani 1 1 d .
H6 H 0.1149 0.2601 0.4124 0.028 Uiso 1 1 calc R
H7 H 0.1112 0.3117 0.3097 0.028 Uiso 1 1 calc R
C9 C 0.26245(19) 0.2042(2) 0.38579(17) 0.0214(5) Uani 1 1 d .
C10 C 0.31188(19) 0.1489(2) 0.48929(17) 0.0237(5) Uani 1 1 d .
C11 C 0.3442(2) 0.0308(3) 0.5078(2) 0.0314(6) Uani 1 1 d .
H8 H 0.3753 0.0012 0.5732 0.038 Uiso 1 1 calc R
H9 H 0.3363 -0.0246 0.4556 0.038 Uiso 1 1 calc R
C12 C 0.3239(2) 0.2382(3) 0.57166(18) 0.0322(6) Uani 1 1 d .
H10 H 0.3380 0.1905 0.6315 0.048 Uiso 1 1 calc R
H11 H 0.2522 0.2870 0.5544 0.048 Uiso 1 1 calc R
H12 H 0.3894 0.2950 0.5824 0.048 Uiso 1 1 calc R
C13 C 0.2544(2) 0.1079(2) 0.30844(16) 0.0210(5) Uani 1 1 d .
C14 C 0.14207(19) 0.0623(2) 0.26075(17) 0.0206(5) Uani 1 1 d .
C15 C 0.1157(2) -0.0275(2) 0.18815(18) 0.0246(5) Uani 1 1 d .
H13 H 0.0385 -0.0580 0.1566 0.030 Uiso 1 1 calc R
C16 C 0.2034(2) -0.0725(2) 0.16222(18) 0.0250(5) Uani 1 1 d .
H14 H 0.1870 -0.1341 0.1125 0.030 Uiso 1 1 calc R
C17 C 0.3165(2) -0.0262(2) 0.21004(17) 0.0231(5) Uani 1 1 d .
C18 C 0.3431(2) 0.0635(2) 0.28258(17) 0.0225(5) Uani 1 1 d .
H15 H 0.4202 0.0942 0.3141 0.027 Uiso 1 1 calc R
C19 C 0.4086(2) -0.0775(2) 0.18012(18) 0.0269(5) Uani 1 1 d .
S1 S -0.09281(5) 0.03635(6) 0.36657(4) 0.02227(17) Uani 1 1 d .
O1 O -0.14008(15) -0.08739(17) 0.35958(13) 0.0316(4) Uani 1 1 d .
O2 O -0.10051(15) 0.11272(18) 0.44351(12) 0.0322(4) Uani 1 1 d .
N1 N 0.03836(16) 0.03158(19) 0.36817(14) 0.0234(4) Uani 1 1 d .
H1 H 0.0916 -0.0207 0.4056 0.028 Uiso 1 1 calc R
C20 C 0.3335(2) 0.3190(2) 0.38075(18) 0.0267(6) Uani 1 1 d .
H16 H 0.4158 0.2960 0.4035 0.040 Uiso 1 1 calc R
H17 H 0.3242 0.3855 0.4224 0.040 Uiso 1 1 calc R
H18 H 0.3059 0.3488 0.3131 0.040 Uiso 1 1 calc R
F1 F 0.51343(12) -0.02691(16) 0.22971(12) 0.0415(4) Uani 1 1 d .
F2 F 0.38625(14) -0.05745(17) 0.08575(11) 0.0425(4) Uani 1 1 d .
F3 F 0.42208(16) -0.20117(15) 0.19253(15) 0.0526(5) Uani 1 1 d .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 '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
C2 C1 C6 123.0(2)
C2 C1 S1 110.64(17)
C6 C1 S1 126.37(18)
C1 C2 C3 119.1(2)
C1 C2 C7 114.0(2)
C3 C2 C7 126.8(2)
C2 C3 C4 118.5(2)
C2 C3 H2 120.8
C4 C3 H2 120.8
C3 C4 C5 121.3(2)
C3 C4 H3 119.4
C5 C4 H3 119.4
C6 C5 C4 120.7(2)
C6 C5 H4 119.7
C4 C5 H4 119.7
C5 C6 C1 117.4(2)
C5 C6 H5 121.3
C1 C6 H5 121.3
N1 C7 C14 109.37(18)
N1 C7 C2 103.45(18)
C14 C7 C2 115.75(19)
N1 C7 C8 114.19(19)
C14 C7 C8 101.81(18)
C2 C7 C8 112.66(18)
C7 C8 C9 106.24(18)
C7 C8 H6 110.5
C9 C8 H6 110.5
C7 C8 H7 110.5
C9 C8 H7 110.5
H6 C8 H7 108.7
C13 C9 C20 111.80(19)
C13 C9 C10 112.40(19)
C20 C9 C10 110.16(19)
C13 C9 C8 100.70(18)
C20 C9 C8 110.84(19)
C10 C9 C8 110.63(18)
C11 C10 C12 120.6(2)
C11 C10 C9 123.1(2)
C12 C10 C9 116.3(2)
C10 C11 H8 120.0
C10 C11 H9 120.0
H8 C11 H9 120.0
C10 C12 H10 109.5
C10 C12 H11 109.5
H10 C12 H11 109.5
C10 C12 H12 109.5
H10 C12 H12 109.5
H11 C12 H12 109.5
C14 C13 C18 119.7(2)
C14 C13 C9 112.1(2)
C18 C13 C9 128.2(2)
C15 C14 C13 121.6(2)
C15 C14 C7 128.0(2)
C13 C14 C7 110.4(2)
C16 C15 C14 119.1(2)
C16 C15 H13 120.4
C14 C15 H13 120.4
C15 C16 C17 119.3(2)
C15 C16 H14 120.4
C17 C16 H14 120.4
C18 C17 C16 121.7(2)
C18 C17 C19 120.7(2)
C16 C17 C19 117.6(2)
C17 C18 C13 118.6(2)
C17 C18 H15 120.7
C13 C18 H15 120.7
F3 C19 F2 105.5(2)
F3 C19 F1 106.3(2)
F2 C19 F1 105.6(2)
F3 C19 C17 113.0(2)
F2 C19 C17 112.8(2)
F1 C19 C17 113.0(2)
O1 S1 O2 115.13(11)
O1 S1 N1 110.83(11)
O2 S1 N1 112.80(11)
O1 S1 C1 112.34(11)
O2 S1 C1 110.73(11)
N1 S1 C1 92.96(10)
C7 N1 S1 115.18(15)
C7 N1 H1 122.4
S1 N1 H1 122.4
C9 C20 H16 109.5
C9 C20 H17 109.5
H16 C20 H17 109.5
C9 C20 H18 109.5
H16 C20 H18 109.5
H17 C20 H18 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 C2 1.385(3)
C1 C6 1.388(3)
C1 S1 1.748(2)
C2 C3 1.388(3)
C2 C7 1.518(3)
C3 C4 1.391(3)
C3 H2 0.9500
C4 C5 1.392(3)
C4 H3 0.9500
C5 C6 1.376(3)
C5 H4 0.9500
C6 H5 0.9500
C7 N1 1.483(3)
C7 C14 1.514(3)
C7 C8 1.552(3)
C8 C9 1.560(3)
C8 H6 0.9900
C8 H7 0.9900
C9 C13 1.517(3)
C9 C20 1.533(3)
C9 C10 1.534(3)
C10 C11 1.320(3)
C10 C12 1.513(3)
C11 H8 0.9500
C11 H9 0.9500
C12 H10 0.9800
C12 H11 0.9800
C12 H12 0.9800
C13 C14 1.389(3)
C13 C18 1.393(3)
C14 C15 1.385(3)
C15 C16 1.384(3)
C15 H13 0.9500
C16 C17 1.400(3)
C16 H14 0.9500
C17 C18 1.382(3)
C17 C19 1.494(3)
C18 H15 0.9500
C19 F3 1.335(3)
C19 F2 1.337(3)
C19 F1 1.339(3)
S1 O1 1.4345(18)
S1 O2 1.4396(18)
S1 N1 1.6325(19)
N1 H1 0.8800
C20 H16 0.9800
C20 H17 0.9800
C20 H18 0.9800
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H1 O2 0.88 2.41 3.020(3) 126.4 3_556
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
C6 C1 C2 C3 -1.6(4)
S1 C1 C2 C3 179.51(18)
C6 C1 C2 C7 177.2(2)
S1 C1 C2 C7 -1.7(3)
C1 C2 C3 C4 0.5(3)
C7 C2 C3 C4 -178.2(2)
C2 C3 C4 C5 0.8(4)
C3 C4 C5 C6 -1.0(4)
C4 C5 C6 C1 -0.1(4)
C2 C1 C6 C5 1.4(4)
S1 C1 C6 C5 -179.90(19)
C1 C2 C7 N1 13.1(3)
C3 C2 C7 N1 -168.2(2)
C1 C2 C7 C14 132.7(2)
C3 C2 C7 C14 -48.6(3)
C1 C2 C7 C8 -110.7(2)
C3 C2 C7 C8 68.0(3)
N1 C7 C8 C9 89.1(2)
C14 C7 C8 C9 -28.6(2)
C2 C7 C8 C9 -153.22(19)
C7 C8 C9 C13 27.8(2)
C7 C8 C9 C20 146.2(2)
C7 C8 C9 C10 -91.3(2)
C13 C9 C10 C11 0.5(3)
C20 C9 C10 C11 -124.9(3)
C8 C9 C10 C11 112.2(3)
C13 C9 C10 C12 179.63(19)
C20 C9 C10 C12 54.2(3)
C8 C9 C10 C12 -68.7(3)
C20 C9 C13 C14 -134.6(2)
C10 C9 C13 C14 100.9(2)
C8 C9 C13 C14 -16.9(2)
C20 C9 C13 C18 45.6(3)
C10 C9 C13 C18 -78.9(3)
C8 C9 C13 C18 163.3(2)
C18 C13 C14 C15 0.5(3)
C9 C13 C14 C15 -179.3(2)
C18 C13 C14 C7 178.9(2)
C9 C13 C14 C7 -0.9(3)
N1 C7 C14 C15 75.6(3)
C2 C7 C14 C15 -40.8(3)
C8 C7 C14 C15 -163.3(2)
N1 C7 C14 C13 -102.6(2)
C2 C7 C14 C13 141.0(2)
C8 C7 C14 C13 18.5(2)
C13 C14 C15 C16 -0.3(4)
C7 C14 C15 C16 -178.4(2)
C14 C15 C16 C17 0.1(4)
C15 C16 C17 C18 -0.1(4)
C15 C16 C17 C19 179.8(2)
C16 C17 C18 C13 0.3(4)
C19 C17 C18 C13 -179.6(2)
C14 C13 C18 C17 -0.5(3)
C9 C13 C18 C17 179.3(2)
C18 C17 C19 F3 120.3(3)
C16 C17 C19 F3 -59.6(3)
C18 C17 C19 F2 -120.2(2)
C16 C17 C19 F2 60.0(3)
C18 C17 C19 F1 -0.5(3)
C16 C17 C19 F1 179.7(2)
C2 C1 S1 O1 -123.13(17)
C6 C1 S1 O1 58.0(2)
C2 C1 S1 O2 106.59(18)
C6 C1 S1 O2 -72.3(2)
C2 C1 S1 N1 -9.16(18)
C6 C1 S1 N1 172.0(2)
C14 C7 N1 S1 -144.39(16)
C2 C7 N1 S1 -20.5(2)
C8 C7 N1 S1 102.30(19)
O1 S1 N1 C7 133.34(16)
O2 S1 N1 C7 -95.90(18)
C1 S1 N1 C7 18.07(18)
