#------------------------------------------------------------------------------
#$Date: 2020-11-04 03:23:28 +0200 (Wed, 04 Nov 2020) $
#$Revision: 258710 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/13/53/4135304.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_4135304
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         'C9 H14 O2'
_chemical_formula_sum            'C9 H14 O2'
_chemical_formula_weight         154.20
_chemical_name_systematic
;
  rac-(S,S,R)-1-methyl-1-ethynyl-1-
 (5-methyl-tetrahydrofuran-2-yl)-methanol
;
_chemical_properties_physical    none
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_audit_block_code                PEV-PA-614-01_12846_100_K
_audit_creation_date             2019-12-18
_audit_creation_method           SHELXL-2018/3
_cell_angle_alpha                90
_cell_angle_beta                 94.822(2)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   8.9181(4)
_cell_length_b                   21.7716(9)
_cell_length_c                   9.1550(4)
_cell_measurement_reflns_used    9168
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      34.3991
_cell_measurement_theta_min      2.4755
_cell_volume                     1771.26(13)
_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 1.000
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_device_type  'Bruker-AXS Kappa Mach3 APEX-II'
_diffrn_measurement_method       'CCD φ- and ω-scans'
_diffrn_radiation_monochromator  'Incoatec Helios mirrors'
_diffrn_radiation_source         1\mS
_diffrn_radiation_type           Mo-K\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0374
_diffrn_reflns_av_unetI/netI     0.0271
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       35
_diffrn_reflns_limit_k_min       -34
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            71080
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         35.262
_diffrn_reflns_theta_min         1.871
_diffrn_source                   'Bruker-Nonius FR591 rotating anode'
_exptl_absorpt_coefficient_mu    0.080
_exptl_absorpt_correction_T_max  0.99680
_exptl_absorpt_correction_T_min  0.99275
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   'SADABS (Bruker AXS, 2012)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.157
_exptl_crystal_description       prism
_exptl_crystal_F_000             672
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent:  diethylether'
_exptl_crystal_size_max          0.132
_exptl_crystal_size_mid          0.111
_exptl_crystal_size_min          0.051
_refine_diff_density_max         0.353
_refine_diff_density_min         -0.262
_refine_diff_density_rms         0.046
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     260
_refine_ls_number_reflns         7848
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.034
_refine_ls_R_factor_all          0.0657
_refine_ls_R_factor_gt           0.0430
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0574P)²+0.2913P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1111
_refine_ls_wR_factor_ref         0.1237
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5775
_reflns_number_total             7848
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            ja0c07808_si_004.cif
_cod_data_source_block           33b
_cod_depositor_comments
'Adding full bibliography for 4135300--4135305.cif.'
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               4135304
_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   0.990
_shelx_estimated_absorpt_t_max   0.996
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -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 0.66852(9) 0.46858(4) 0.13366(8) 0.01834(13) Uani 1 1 d . . . . .
C2 C 0.73466(10) 0.53378(4) 0.14694(9) 0.02326(15) Uani 1 1 d . . . . .
H2A H 0.816925 0.539086 0.081851 0.028 Uiso 1 1 calc R U . . .
H2B H 0.656213 0.565113 0.121966 0.028 Uiso 1 1 calc R U . . .
C3 C 0.79404(10) 0.53839(4) 0.30784(9) 0.02373(15) Uani 1 1 d . . . . .
H3A H 0.899240 0.523680 0.322926 0.028 Uiso 1 1 calc R U . . .
H3B H 0.788920 0.581151 0.343852 0.028 Uiso 1 1 calc R U . . .
C4 C 0.68852(9) 0.49687(4) 0.38350(8) 0.02292(15) Uani 1 1 d . . . . .
C5 C 0.75270(13) 0.46890(5) 0.52570(10) 0.0357(2) Uani 1 1 d . . . . .
H5A H 0.846861 0.447611 0.510103 0.054 Uiso 1 1 calc R U . . .
H5B H 0.680503 0.439515 0.560593 0.054 Uiso 1 1 calc R U . . .
H5C H 0.772517 0.501359 0.598944 0.054 Uiso 1 1 calc R U . . .
C6 C 0.76084(9) 0.42122(3) 0.05456(7) 0.01755(13) Uani 1 1 d . . . . .
C7 C 0.91452(9) 0.41447(3) 0.12824(8) 0.01924(14) Uani 1 1 d . . . . .
C8 C 1.04025(10) 0.40894(4) 0.18306(9) 0.02368(15) Uani 1 1 d . . . . .
H8 H 1.140171 0.404538 0.226628 0.028 Uiso 1 1 calc R U . . .
C9 C 0.77032(10) 0.44053(4) -0.10481(8) 0.02308(15) Uani 1 1 d . . . . .
H9A H 0.669185 0.449863 -0.149540 0.035 Uiso 1 1 calc R U . . .
H9B H 0.813879 0.407016 -0.158844 0.035 Uiso 1 1 calc R U . . .
H9C H 0.833981 0.477105 -0.108273 0.035 Uiso 1 1 calc R U . . .
C11 C 0.48611(10) 0.28067(4) 0.33166(10) 0.02767(18) Uani 1 1 d . . . . .
C16 C 0.40005(9) 0.32492(4) 0.42455(9) 0.02116(14) Uani 1 1 d . . . . .
C17 C 0.47219(9) 0.33109(4) 0.57541(9) 0.02516(16) Uani 1 1 d . . . . .
C18 C 0.52420(10) 0.33483(5) 0.69970(10) 0.02905(18) Uani 1 1 d . . . . .
H18 H 0.565545 0.337798 0.798514 0.035 Uiso 1 1 calc R U . . .
C19 C 0.23911(9) 0.30182(4) 0.43055(10) 0.02544(16) Uani 1 1 d . . . . .
H19A H 0.193433 0.295183 0.330666 0.038 Uiso 1 1 calc R U . . .
H19B H 0.180384 0.332391 0.479818 0.038 Uiso 1 1 calc R U . . .
H19C H 0.240154 0.263053 0.485029 0.038 Uiso 1 1 calc R U . . .
H1 H 0.5659(12) 0.4684(5) 0.0797(12) 0.022(3) Uiso 1 1 d . . . . .
H2 H 0.6714(16) 0.3517(7) 0.1364(16) 0.045(4) Uiso 1 1 d . . . . .
H4 H 0.4784(16) 0.3969(7) 0.3355(15) 0.041(3) Uiso 1 1 d . . . . .
H4A H 0.5932(13) 0.5188(5) 0.3985(12) 0.026(3) Uiso 1 1 d . . . . .
H11 H 0.4251(13) 0.2813(5) 0.2308(13) 0.029(3) Uiso 1 1 d . . . . .
O1 O 0.65372(6) 0.44758(3) 0.28030(6) 0.02097(12) Uani 1 1 d . . . . .
O2 O 0.68400(7) 0.36357(3) 0.04955(6) 0.02176(12) Uani 1 1 d . . . . .
O3 O 0.63192(7) 0.30608(3) 0.31268(7) 0.02799(14) Uani 1 1 d . . . . .
O4 O 0.38897(7) 0.38334(3) 0.35358(7) 0.02256(12) Uani 1 1 d . . . . .
C12A C 0.5009(3) 0.21256(11) 0.3794(3) 0.0262(4) Uani 0.6 1 d . . P A 1
H12A H 0.428838 0.201955 0.451972 0.031 Uiso 0.6 1 calc R U P A 1
H12B H 0.486089 0.184442 0.294407 0.031 Uiso 0.6 1 calc R U P A 1
C13A C 0.66150(18) 0.21116(7) 0.44677(19) 0.0304(3) Uani 0.6 1 d . . P A 1
H13A H 0.706165 0.169770 0.439168 0.036 Uiso 0.6 1 calc R U P A 1
H13B H 0.667753 0.223700 0.551045 0.036 Uiso 0.6 1 calc R U P A 1
C14A C 0.7408(8) 0.2590(3) 0.3515(6) 0.0286(9) Uani 0.6 1 d . . P A 1
H14A H 0.776159 0.239153 0.261982 0.034 Uiso 0.6 1 calc R U P A 1
C15A C 0.8678(3) 0.29091(13) 0.4384(3) 0.0438(6) Uani 0.6 1 d . . P A 1
H15A H 0.912739 0.321352 0.376403 0.066 Uiso 0.6 1 calc R U P A 1
H15B H 0.944254 0.260700 0.472877 0.066 Uiso 0.6 1 calc R U P A 1
H15C H 0.829508 0.311557 0.522841 0.066 Uiso 0.6 1 calc R U P A 1
C12B C 0.5353(4) 0.22221(17) 0.4188(4) 0.0301(7) Uani 0.4 1 d . . P A 2
H12C H 0.550161 0.230779 0.525229 0.036 Uiso 0.4 1 calc R U P A 2
H12D H 0.460216 0.188940 0.401562 0.036 Uiso 0.4 1 calc R U P A 2
C13B C 0.6827(3) 0.20556(10) 0.3574(3) 0.0360(6) Uani 0.4 1 d . . P A 2
H13C H 0.665778 0.189372 0.256255 0.043 Uiso 0.4 1 calc R U P A 2
H13D H 0.739282 0.174839 0.419736 0.043 Uiso 0.4 1 calc R U P A 2
C14B C 0.7647(12) 0.2672(5) 0.3602(11) 0.039(2) Uani 0.4 1 d . . P A 2
H14B H 0.833478 0.267039 0.279373 0.047 Uiso 0.4 1 calc R U P A 2
C15B C 0.8500(4) 0.2870(2) 0.4922(4) 0.0445(10) Uani 0.4 1 d . . P A 2
H15D H 0.877677 0.330297 0.482673 0.067 Uiso 0.4 1 calc R U P A 2
H15E H 0.941430 0.262077 0.508076 0.067 Uiso 0.4 1 calc R U P A 2
H15F H 0.789057 0.282140 0.575624 0.067 Uiso 0.4 1 calc R U P A 2
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'
O O 0.0106 0.0060 '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 1.00 0.0250
-1.00 0.00 -1.00 0.0250
1.00 2.00 0.00 0.0300
-1.00 -2.00 0.00 0.0550
0.00 2.00 1.00 0.0250
0.00 -2.00 -1.00 0.0450
0.00 -2.00 1.00 0.0500
-1.00 1.00 0.00 0.0400
1.00 -1.00 0.00 0.0400
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
O1 C1 C2 106.56(6) . . ?
O1 C1 C6 108.78(6) . . ?
C2 C1 C6 116.04(6) . . ?
O1 C1 H1 107.9(6) . . ?
C2 C1 H1 111.7(6) . . ?
C6 C1 H1 105.5(6) . . ?
C3 C2 C1 103.68(6) . . ?
C3 C2 H2A 111.0 . . ?
C1 C2 H2A 111.0 . . ?
C3 C2 H2B 111.0 . . ?
C1 C2 H2B 111.0 . . ?
H2A C2 H2B 109.0 . . ?
C4 C3 C2 102.94(6) . . ?
C4 C3 H3A 111.2 . . ?
C2 C3 H3A 111.2 . . ?
C4 C3 H3B 111.2 . . ?
C2 C3 H3B 111.2 . . ?
H3A C3 H3B 109.1 . . ?
O1 C4 C5 108.04(7) . . ?
O1 C4 C3 104.57(6) . . ?
C5 C4 C3 115.55(7) . . ?
O1 C4 H4A 107.9(7) . . ?
C5 C4 H4A 110.0(7) . . ?
C3 C4 H4A 110.4(7) . . ?
C4 C5 H5A 109.5 . . ?
C4 C5 H5B 109.5 . . ?
H5A C5 H5B 109.5 . . ?
C4 C5 H5C 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
O2 C6 C7 110.49(6) . . ?
O2 C6 C9 106.02(6) . . ?
C7 C6 C9 109.78(6) . . ?
O2 C6 C1 109.25(6) . . ?
C7 C6 C1 111.29(6) . . ?
C9 C6 C1 109.87(6) . . ?
C8 C7 C6 177.78(8) . . ?
C7 C8 H8 180.0 . . ?
C6 C9 H9A 109.5 . . ?
C6 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C6 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
O3 C11 C16 109.00(7) . . ?
O3 C11 C12B 99.15(15) . . ?
C16 C11 C12B 111.39(15) . . ?
O3 C11 C12A 110.25(11) . . ?
C16 C11 C12A 118.69(11) . . ?
O3 C11 H11 107.5(7) . . ?
C16 C11 H11 103.7(7) . . ?
C12B C11 H11 125.3(7) . . ?
C12A C11 H11 106.9(7) . . ?
O4 C16 C17 110.59(7) . . ?
O4 C16 C19 106.29(6) . . ?
C17 C16 C19 109.43(7) . . ?
O4 C16 C11 109.03(6) . . ?
C17 C16 C11 112.10(7) . . ?
C19 C16 C11 109.22(7) . . ?
C18 C17 C16 176.76(9) . . ?
C17 C18 H18 180.0 . . ?
C16 C19 H19A 109.5 . . ?
C16 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C16 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C1 O1 C4 110.08(6) . . ?
C6 O2 H2 109.7(9) . . ?
C14A O3 C11 107.2(3) . . ?
C11 O3 C14B 116.8(5) . . ?
C16 O4 H4 110.9(9) . . ?
C13A C12A C11 100.95(15) . . ?
C13A C12A H12A 111.6 . . ?
C11 C12A H12A 111.6 . . ?
C13A C12A H12B 111.6 . . ?
C11 C12A H12B 111.6 . . ?
H12A C12A H12B 109.4 . . ?
C12A C13A C14A 102.5(3) . . ?
C12A C13A H13A 111.3 . . ?
C14A C13A H13A 111.3 . . ?
C12A C13A H13B 111.3 . . ?
C14A C13A H13B 111.3 . . ?
H13A C13A H13B 109.2 . . ?
O3 C14A C15A 105.3(5) . . ?
O3 C14A C13A 106.6(4) . . ?
C15A C14A C13A 111.7(4) . . ?
O3 C14A H14A 111.0 . . ?
C15A C14A H14A 111.0 . . ?
C13A C14A H14A 111.0 . . ?
C14A C15A H15A 109.5 . . ?
C14A C15A H15B 109.5 . . ?
H15A C15A H15B 109.5 . . ?
C14A C15A H15C 109.5 . . ?
H15A C15A H15C 109.5 . . ?
H15B C15A H15C 109.5 . . ?
C13B C12B C11 102.9(3) . . ?
C13B C12B H12C 111.2 . . ?
C11 C12B H12C 111.2 . . ?
C13B C12B H12D 111.2 . . ?
C11 C12B H12D 111.2 . . ?
H12C C12B H12D 109.1 . . ?
C12B C13B C14B 102.3(4) . . ?
C12B C13B H13C 111.3 . . ?
C14B C13B H13C 111.3 . . ?
C12B C13B H13D 111.3 . . ?
C14B C13B H13D 111.3 . . ?
H13C C13B H13D 109.2 . . ?
C15B C14B O3 115.2(7) . . ?
C15B C14B C13B 119.8(8) . . ?
O3 C14B C13B 97.3(6) . . ?
C15B C14B H14B 107.9 . . ?
O3 C14B H14B 107.9 . . ?
C13B C14B H14B 107.9 . . ?
C14B C15B H15D 109.5 . . ?
C14B C15B H15E 109.5 . . ?
H15D C15B H15E 109.5 . . ?
C14B C15B H15F 109.5 . . ?
H15D C15B H15F 109.5 . . ?
H15E C15B H15F 109.5 . . ?
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 O1 1.4348(9) . ?
C1 C2 1.5381(11) . ?
C1 C6 1.5382(11) . ?
C1 H1 1.003(11) . ?
C2 C3 1.5262(11) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 C4 1.5139(12) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 O1 1.4461(10) . ?
C4 C5 1.5060(12) . ?
C4 H4A 0.995(11) . ?
C5 H5A 0.9800 . ?
C5 H5B 0.9800 . ?
C5 H5C 0.9800 . ?
C6 O2 1.4289(9) . ?
C6 C7 1.4831(11) . ?
C6 C9 1.5275(10) . ?
C7 C8 1.1955(12) . ?
C8 H8 0.9500 . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C11 O3 1.4370(11) . ?
C11 C16 1.5329(12) . ?
C11 C12B 1.546(4) . ?
C11 C12A 1.549(3) . ?
C11 H11 1.032(12) . ?
C16 O4 1.4280(10) . ?
C16 C17 1.4799(12) . ?
C16 C19 1.5262(12) . ?
C17 C18 1.1948(12) . ?
C18 H18 0.9500 . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
O2 H2 0.852(15) . ?
O3 C14A 1.436(7) . ?
O3 C14B 1.490(10) . ?
O4 H4 0.880(14) . ?
C12A C13A 1.511(3) . ?
C12A H12A 0.9900 . ?
C12A H12B 0.9900 . ?
C13A C14A 1.565(8) . ?
C13A H13A 0.9900 . ?
C13A H13B 0.9900 . ?
C14A C15A 1.500(7) . ?
C14A H14A 1.0000 . ?
C15A H15A 0.9800 . ?
C15A H15B 0.9800 . ?
C15A H15C 0.9800 . ?
C12B C13B 1.516(5) . ?
C12B H12C 0.9900 . ?
C12B H12D 0.9900 . ?
C13B C14B 1.527(11) . ?
C13B H13C 0.9900 . ?
C13B H13D 0.9900 . ?
C14B C15B 1.439(10) . ?
C14B H14B 1.0000 . ?
C15B H15D 0.9800 . ?
C15B H15E 0.9800 . ?
C15B H15F 0.9800 . ?
