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#$Date: 2020-11-04 03:23:28 +0200 (Wed, 04 Nov 2020) $
#$Revision: 258710 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/13/53/4135301.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_4135301
loop_
_publ_author_name
'Peil, Sebastian'
'Bistoni, Giovanni'
'Goddard, Richard'
'Fürstner, Alois'
_publ_section_title
;
 Hydrogenative Metathesis of Enynes via Piano-Stool Ruthenium Carbene
 Complexes Formed by Alkyne gem-Hydrogenation.
;
_journal_issue                   43
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              18541
_journal_page_last               18553
_journal_paper_doi               10.1021/jacs.0c07808
_journal_volume                  142
_journal_year                    2020
_chemical_formula_moiety         'C8 H14 O2 Si'
_chemical_formula_sum            'C8 H14 O2 Si'
_chemical_formula_weight         170.28
_chemical_name_systematic
;
 3-(trimethylsilyl)methyl-(5H)-furan-2-one
;
_chemical_properties_physical    none
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_audit_block_code                PEV-PA-595-01_12988_100_K
_audit_creation_date             2020-03-11
_audit_creation_method           SHELXL-2018/3
_cell_angle_alpha                90
_cell_angle_beta                 107.264(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   13.8465(6)
_cell_length_b                   6.4641(3)
_cell_length_c                   11.3247(5)
_cell_measurement_reflns_used    8455
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      63.0166
_cell_measurement_theta_min      3.3424
_cell_volume                     967.95(8)
_computing_cell_refinement       'SAINT software (Bruker AXS, 2004)'
_computing_data_collection       'APEX3 (Bruker AXS, 2005-2017)'
_computing_data_reduction        'SAINT software (Bruker AXS, 2004)'
_computing_molecular_graphics    'DIAMOND (Crystal Impact GbR, 1997-2014)'
_computing_structure_refinement  'SHELXL (G. M. Sheldrick, 2015)'
_computing_structure_solution    'SHELXT (G. M. Sheldrick, 2015)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 66.67
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type  'Bruker-AXS Kappa Mach3 APEX-II'
_diffrn_measurement_method       'CCD φ- and ω-scans'
_diffrn_radiation_monochromator  'MONTEL graded multilayer optic'
_diffrn_radiation_source         '0.2 x 2mm^2^ focus rotating anode'
_diffrn_radiation_type           Cu-K\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0552
_diffrn_reflns_av_unetI/netI     0.0268
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            17601
_diffrn_reflns_point_group_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        63.198
_diffrn_reflns_theta_max         63.198
_diffrn_reflns_theta_min         3.342
_diffrn_source                   'Bruker-Nonius FR591 rotating anode'
_exptl_absorpt_coefficient_mu    1.780
_exptl_absorpt_correction_T_max  0.98217
_exptl_absorpt_correction_T_min  0.72475
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   'SADABS (Bruker AXS, 2012)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.168
_exptl_crystal_description       plate
_exptl_crystal_F_000             368
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent:  diethylether'
_exptl_crystal_size_max          0.330
_exptl_crystal_size_mid          0.145
_exptl_crystal_size_min          0.010
_refine_diff_density_max         0.268
_refine_diff_density_min         -0.282
_refine_diff_density_rms         0.042
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     103
_refine_ls_number_reflns         1560
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.046
_refine_ls_R_factor_all          0.0368
_refine_ls_R_factor_gt           0.0322
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0432P)²+0.5315P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0827
_refine_ls_wR_factor_ref         0.0863
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1407
_reflns_number_total             1560
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            ja0c07808_si_006.cif
_cod_data_source_block           56
_cod_depositor_comments
'Adding full bibliography for 4135300--4135305.cif.'
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               4135301
_shelx_shelxl_version_number     2018/3
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_min   0.591
_shelx_estimated_absorpt_t_max   0.982
loop_
_space_group_symop_operation_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.37690(12) 0.4313(2) 0.45190(15) 0.0213(4) Uani 1 1 d . . . . .
C2 C 0.36564(12) 0.4785(2) 0.32073(14) 0.0203(4) Uani 1 1 d . . . . .
C3 C 0.41251(12) 0.3287(3) 0.27841(15) 0.0234(4) Uani 1 1 d . . . . .
H3 H 0.416757 0.320677 0.196333 0.028 Uiso 1 1 calc R U . . .
C4 C 0.45726(13) 0.1756(3) 0.37759(15) 0.0242(4) Uani 1 1 d . . . . .
H4A H 0.428276 0.036296 0.353938 0.029 Uiso 1 1 calc R U . . .
H4B H 0.531579 0.168319 0.394812 0.029 Uiso 1 1 calc R U . . .
C5 C 0.30759(13) 0.6639(3) 0.26022(15) 0.0236(4) Uani 1 1 d . . . . .
H5A H 0.346482 0.735456 0.211770 0.028 Uiso 1 1 calc R U . . .
H5B H 0.300868 0.760559 0.325151 0.028 Uiso 1 1 calc R U . . .
C6 C 0.10781(14) 0.4453(3) 0.24087(18) 0.0339(4) Uani 1 1 d . . . . .
H6A H 0.099718 0.526204 0.310504 0.051 Uiso 1 1 calc R U . . .
H6B H 0.146118 0.319098 0.272029 0.051 Uiso 1 1 calc R U . . .
H6C H 0.041060 0.408202 0.185575 0.051 Uiso 1 1 calc R U . . .
C7 C 0.11191(15) 0.8514(3) 0.10298(19) 0.0350(4) Uani 1 1 d . . . . .
H7A H 0.044786 0.824677 0.045263 0.052 Uiso 1 1 calc R U . . .
H7B H 0.151652 0.934063 0.061638 0.052 Uiso 1 1 calc R U . . .
H7C H 0.104819 0.927222 0.174890 0.052 Uiso 1 1 calc R U . . .
C8 C 0.19054(14) 0.4537(3) 0.01896(17) 0.0329(4) Uani 1 1 d . . . . .
H8A H 0.123307 0.420898 -0.036660 0.049 Uiso 1 1 calc R U . . .
H8B H 0.227607 0.325196 0.047607 0.049 Uiso 1 1 calc R U . . .
H8C H 0.227697 0.537244 -0.025297 0.049 Uiso 1 1 calc R U . . .
O1 O 0.43095(9) 0.25262(17) 0.48393(10) 0.0246(3) Uani 1 1 d . . . . .
O2 O 0.34623(9) 0.52529(19) 0.52557(10) 0.0276(3) Uani 1 1 d . . . . .
Si1 Si 0.17722(3) 0.60188(7) 0.15442(4) 0.02265(17) 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'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Si Si 0.2541 0.3302 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-1.00 0.00 0.00 0.0050
1.00 0.00 0.00 0.0050
0.00 -1.00 -1.00 0.0700
0.00 1.00 1.00 0.0600
0.00 1.00 -1.00 0.1200
0.00 -1.00 1.00 0.1300
0.00 0.00 -1.00 0.1400
0.00 0.00 1.00 0.1450
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
_geom_angle_publ_flag
O2 C1 O1 121.33(15) . . ?
O2 C1 C2 129.54(15) . . ?
O1 C1 C2 109.13(13) . . ?
C3 C2 C1 107.08(14) . . ?
C3 C2 C5 132.28(15) . . ?
C1 C2 C5 120.62(14) . . ?
C2 C3 C4 110.51(14) . . ?
C2 C3 H3 124.7 . . ?
C4 C3 H3 124.7 . . ?
O1 C4 C3 104.39(13) . . ?
O1 C4 H4A 110.9 . . ?
C3 C4 H4A 110.9 . . ?
O1 C4 H4B 110.9 . . ?
C3 C4 H4B 110.9 . . ?
H4A C4 H4B 108.9 . . ?
C2 C5 Si1 113.82(11) . . ?
C2 C5 H5A 108.8 . . ?
Si1 C5 H5A 108.8 . . ?
C2 C5 H5B 108.8 . . ?
Si1 C5 H5B 108.8 . . ?
H5A C5 H5B 107.7 . . ?
Si1 C6 H6A 109.5 . . ?
Si1 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
Si1 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
Si1 C7 H7A 109.5 . . ?
Si1 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
Si1 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
Si1 C8 H8A 109.5 . . ?
Si1 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
Si1 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C1 O1 C4 108.88(12) . . ?
C7 Si1 C6 110.98(9) . . ?
C7 Si1 C8 110.25(9) . . ?
C6 Si1 C8 110.26(9) . . ?
C7 Si1 C5 107.41(8) . . ?
C6 Si1 C5 109.10(8) . . ?
C8 Si1 C5 108.77(8) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 O2 1.207(2) . ?
C1 O1 1.365(2) . ?
C1 C2 1.479(2) . ?
C2 C3 1.332(2) . ?
C2 C5 1.492(2) . ?
C3 C4 1.487(2) . ?
C3 H3 0.9500 . ?
C4 O1 1.4461(19) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 Si1 1.8898(17) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C6 Si1 1.8613(18) . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C6 H6C 0.9800 . ?
C7 Si1 1.8564(19) . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C8 Si1 1.8633(18) . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 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_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O2 C1 C2 C3 -179.92(17) . . . . ?
O1 C1 C2 C3 0.10(17) . . . . ?
O2 C1 C2 C5 -1.3(3) . . . . ?
O1 C1 C2 C5 178.70(13) . . . . ?
C1 C2 C3 C4 -0.16(18) . . . . ?
C5 C2 C3 C4 -178.53(16) . . . . ?
C2 C3 C4 O1 0.17(18) . . . . ?
C3 C2 C5 Si1 74.7(2) . . . . ?
C1 C2 C5 Si1 -103.47(15) . . . . ?
O2 C1 O1 C4 -179.97(15) . . . . ?
C2 C1 O1 C4 0.01(17) . . . . ?
C3 C4 O1 C1 -0.10(16) . . . . ?
C2 C5 Si1 C7 173.51(12) . . . . ?
C2 C5 Si1 C6 53.13(14) . . . . ?
C2 C5 Si1 C8 -67.17(14) . . . . ?
