#------------------------------------------------------------------------------
#$Date: 2017-10-13 14:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201982 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/11/31/4113181.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_4113181
loop_
_publ_author_name
'Gereon Altenhoff'
'Richard Goddard'
'Christian W. Lehmann'
'Frank Glorius'
_publ_section_title
;
 Sterically Demanding, Bioxazoline-Derived N-Heterocyclic Carbene Ligands
 with Restricted Flexibility for Catalysis
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              15195
_journal_page_last               15201
_journal_paper_doi               10.1021/ja045349r
_journal_volume                  126
_journal_year                    2004
_chemical_compound_source        dichloromethane/pentane
_chemical_formula_moiety         'C11 H17 N2 O2 1+, C F3 O3 S 1-'
_chemical_formula_sum            'C12 H17 F3 N2 O5 S'
_chemical_formula_weight         358.34
_chemical_name_common            IBiox(Me)4.HOTf
_chemical_name_systematic
; 
 4,4,11,11-tetramethyl-6,9-dioxa-1,3-diazatricyclo[6.3.0.0^3,7^]undeca-
 7-ene-2-onium trifluoromethanesulfonate 
;
_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
_cell_angle_alpha                90.00
_cell_angle_beta                 93.873(1)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.2288(2)
_cell_length_b                   9.9771(2)
_cell_length_c                   17.2853(3)
_cell_measurement_reflns_used    63705
_cell_measurement_temperature    100
_cell_measurement_theta_max      31.0
_cell_measurement_theta_min      2.91
_cell_volume                     1587.94(5)
_computing_cell_refinement       'Denzo / Scalepack (Otwinowski 1997)'
_computing_data_collection       'Collect software (Nonius, 1998)'
_computing_data_reduction        'Denzo / Scalepack (Otwinowski 1997)'
_computing_molecular_graphics    'DIAMOND (Crystal Impact GbR, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      100
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Nonius KappaCCD'
_diffrn_measurement_method       'CCD ω-scan'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         '0.3 mm focus rotating anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1115
_diffrn_reflns_av_sigmaI/netI    0.0527
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            38655
_diffrn_reflns_theta_full        30.97
_diffrn_reflns_theta_max         30.97
_diffrn_reflns_theta_min         5.15
_diffrn_standards_decay_%        0.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.261
_exptl_absorpt_correction_T_max  0.98422
_exptl_absorpt_correction_T_min  0.96382
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   'XPREP, Siemens (1995)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.499
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    none
_exptl_crystal_description       plate
_exptl_crystal_F_000             744
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.775
_refine_diff_density_min         -0.846
_refine_diff_density_rms         0.158
_refine_ls_extinction_coef       0.007(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   0.974
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     209
_refine_ls_number_reflns         5021
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.974
_refine_ls_R_factor_all          0.0893
_refine_ls_R_factor_gt           0.0552
_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)+(0.1314P)²+0.2971P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1599
_refine_ls_wR_factor_ref         0.1878
_reflns_number_gt                3640
_reflns_number_total             5021
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            ja045349rsi20040812_055233.cif
_cod_data_source_block           IBiox(Me)4.HOTf
_cod_depositor_comments
;
The following automatic conversions were performed:

'_exptl_crystal_density_meas' value 'none' was changed to '?' - the
value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas 
;
_cod_database_code               4113181
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 0.2021(2) 1.38633(19) -0.07570(11) 0.0177(4) Uani 1 1 d .
H1 H 0.1778 1.4380 -0.0337 0.021 Uiso 1 1 calc R
C2 C 0.2474(2) 1.14353(19) -0.01989(11) 0.0182(4) Uani 1 1 d .
C3 C 0.2406(2) 1.0271(2) -0.07947(11) 0.0217(4) Uani 1 1 d .
H3A H 0.3008 0.9529 -0.0604 0.026 Uiso 1 1 calc R
H3B H 0.1415 0.9954 -0.0887 0.026 Uiso 1 1 calc R
C4 C 0.2615(2) 1.2128(2) -0.14911(11) 0.0190(4) Uani 1 1 d .
C5 C 0.2505(2) 1.3226(2) -0.19509(11) 0.0194(4) Uani 1 1 d .
C6 C 0.2663(3) 1.5061(2) -0.26781(13) 0.0323(5) Uani 1 1 d .
H6A H 0.2169 1.5436 -0.3142 0.039 Uiso 1 1 calc R
H6B H 0.3665 1.5360 -0.2649 0.039 Uiso 1 1 calc R
C7 C 0.1906(2) 1.5520(2) -0.19474(12) 0.0206(4) Uani 1 1 d .
C8 C 0.3952(2) 1.1545(2) 0.02496(12) 0.0231(4) Uani 1 1 d .
H8A H 0.4703 1.1563 -0.0108 0.035 Uiso 1 1 calc R
H8B H 0.4094 1.0786 0.0588 0.035 Uiso 1 1 calc R
H8C H 0.3989 1.2354 0.0551 0.035 Uiso 1 1 calc R
C9 C 0.1236(2) 1.1400(2) 0.03387(12) 0.0227(4) Uani 1 1 d .
H9A H 0.0327 1.1332 0.0036 0.034 Uiso 1 1 calc R
H9B H 0.1246 1.2207 0.0642 0.034 Uiso 1 1 calc R
H9C H 0.1352 1.0640 0.0678 0.034 Uiso 1 1 calc R
C10 C 0.2655(3) 1.6718(2) -0.15636(15) 0.0358(6) Uani 1 1 d .
H10A H 0.3676 1.6540 -0.1482 0.054 Uiso 1 1 calc R
H10B H 0.2256 1.6886 -0.1074 0.054 Uiso 1 1 calc R
H10C H 0.2509 1.7490 -0.1891 0.054 Uiso 1 1 calc R
C11 C 0.0283(3) 1.5718(3) -0.20985(18) 0.0425(7) Uani 1 1 d .
H11A H -0.0137 1.4931 -0.2342 0.064 Uiso 1 1 calc R
H11B H 0.0105 1.6477 -0.2433 0.064 Uiso 1 1 calc R
H11C H -0.0148 1.5873 -0.1616 0.064 Uiso 1 1 calc R
C12 C 0.3497(2) 1.9030(2) -0.37386(14) 0.0281(5) Uani 1 1 d .
F1 F 0.44520(16) 1.92304(16) -0.42753(10) 0.0402(4) Uani 1 1 d .
F2 F 0.30656(18) 2.02373(17) -0.35150(12) 0.0514(5) Uani 1 1 d .
F3 F 0.42046(17) 1.8453(2) -0.31336(10) 0.0494(5) Uani 1 1 d .
N1 N 0.23002(17) 1.25530(16) -0.07610(9) 0.0169(3) Uani 1 1 d .
N2 N 0.21646(18) 1.42791(16) -0.14829(9) 0.0176(3) Uani 1 1 d .
O1 O 0.29448(18) 1.08128(14) -0.15119(8) 0.0242(3) Uani 1 1 d .
O2 O 0.25963(19) 1.35944(15) -0.27006(8) 0.0256(3) Uani 1 1 d .
O3 O 0.12741(18) 1.88461(17) -0.47130(10) 0.0314(4) Uani 1 1 d .
O4 O 0.26575(19) 1.68228(16) -0.43945(10) 0.0312(4) Uani 1 1 d .
O5 O 0.11357(17) 1.77967(16) -0.34510(9) 0.0268(3) Uani 1 1 d .
S1 S 0.19670(5) 1.80074(5) -0.41158(3) 0.01890(16) 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 0.0033 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'
F F 0.0171 0.0103 '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'
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_publ_flag
N1 C1 N2 105.55(16) y
N1 C2 C9 111.46(16) y
N1 C2 C8 109.42(16) y
C9 C2 C8 111.95(17) y
N1 C2 C3 97.51(14) y
C9 C2 C3 112.96(17) y
C8 C2 C3 112.67(17) y
O1 C3 C2 106.47(15) y
O1 C4 C5 141.32(17) y
O1 C4 N1 112.67(16) y
C5 C4 N1 105.99(17) y
C4 C5 O2 140.69(18) y
C4 C5 N2 106.51(16) y
O2 C5 N2 112.78(16) y
O2 C6 C7 107.21(17) y
N2 C7 C10 111.69(18) y
N2 C7 C11 108.84(17) y
C10 C7 C11 112.9(2) y
N2 C7 C6 97.40(16) y
C10 C7 C6 111.86(19) y
C11 C7 C6 113.1(2) y
F3 C12 F2 107.7(2) y
F3 C12 F1 107.43(19) y
F2 C12 F1 106.9(2) y
F3 C12 S1 111.50(17) y
F2 C12 S1 111.66(16) y
F1 C12 S1 111.45(15) y
C1 N1 C4 111.05(16) y
C1 N1 C2 138.40(16) y
C4 N1 C2 110.37(15) y
C1 N2 C5 110.88(16) y
C1 N2 C7 138.00(17) y
C5 N2 C7 110.68(15) y
C4 O1 C3 104.22(14) y
C5 O2 C6 104.51(15) y
O5 S1 O4 114.75(10) y
O5 S1 O3 114.90(10) y
O4 S1 O3 114.89(11) y
O5 S1 C12 103.73(10) y
O4 S1 C12 103.23(10) y
O3 S1 C12 103.05(11) y
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
C1 N1 1.333(2) y
C1 N2 1.337(2) y
C2 N1 1.481(2) y
C2 C9 1.521(3) y
C2 C8 1.527(3) y
C2 C3 1.551(3) y
C3 O1 1.470(2) y
C4 O1 1.348(2) y
C4 C5 1.354(3) y
C4 N1 1.381(2) y
C5 O2 1.355(2) y
C5 N2 1.375(2) y
C6 O2 1.465(3) y
C6 C7 1.553(3) y
C7 N2 1.486(2) y
C7 C10 1.512(3) y
C7 C11 1.516(3) y
C12 F3 1.326(3) y
C12 F2 1.334(3) y
C12 F1 1.337(3) y
C12 S1 1.827(2) y
O3 S1 1.4440(16) y
O4 S1 1.4411(16) y
O5 S1 1.4396(15) y
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30660482
