#------------------------------------------------------------------------------
#$Date: 2016-02-16 22:30:59 +0200 (Tue, 16 Feb 2016) $
#$Revision: 176467 $
#$URL: svn://www.crystallography.net/cod/cif/4/06/87/4068785.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_4068785
loop_
_publ_author_name
'Yamauchi, Yoshihiro'
'Miyake, Yoshihiro'
'Nishibayashi, Yoshiaki'
_publ_section_title
;
 Ruthenium-Catalyzed Oxypropargylation of Alkenes
;
_journal_issue                   1
_journal_name_full               Organometallics
_journal_page_first              48
_journal_paper_doi               10.1021/om801092a
_journal_volume                  28
_journal_year                    2009
_chemical_formula_moiety         'C16 H20 O2 '
_chemical_formula_sum            'C16 H20 O2'
_chemical_formula_weight         244.33
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      14
_symmetry_space_group_name_Hall  '-P 2yab'
_symmetry_space_group_name_H-M   'P 1 21/a 1'
_cell_angle_alpha                90.0000
_cell_angle_beta                 107.737(4)
_cell_angle_gamma                90.0000
_cell_formula_units_Z            4
_cell_length_a                   9.0679(11)
_cell_length_b                   16.1554(17)
_cell_length_c                   10.0257(11)
_cell_measurement_reflns_used    6830
_cell_measurement_temperature    173.1
_cell_measurement_theta_max      27.4
_cell_measurement_theta_min      3.3
_cell_volume                     1398.9(3)
_computing_cell_refinement       PROCESS-AUTO
_computing_data_collection       PROCESS-AUTO
_computing_data_reduction        CrystalStructure
_computing_publication_material  'CrystalStructure 3.8'
_computing_structure_refinement  CRYSTALS
_computing_structure_solution    SIR97
_diffrn_detector_area_resol_mean 10.00
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Rigaku RAXIS-RAPID'
_diffrn_measurement_method       ω
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71075
_diffrn_reflns_av_R_equivalents  0.054
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            13571
_diffrn_reflns_theta_full        27.47
_diffrn_reflns_theta_max         27.47
_exptl_absorpt_coefficient_mu    0.075
_exptl_absorpt_correction_T_max  0.982
_exptl_absorpt_correction_T_min  0.740
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
    Higashi, T. (1995). Program for Absorption Correction.
    Rigaku Corporation, Tokyo, Japan.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.160
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             528.00
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.25
_refine_diff_density_max         0.52
_refine_diff_density_min         -0.60
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.000
_refine_ls_hydrogen_treatment    refall
_refine_ls_number_parameters     183
_refine_ls_number_reflns         3181
_refine_ls_R_factor_gt           0.0519
_refine_ls_shift/su_max          0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[0.0003Fo² + 1.4670σ(Fo²)]/(4Fo²)'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.1282
_reflns_number_gt                1289
_reflns_number_total             3181
_reflns_threshold_expression     F²>2.0σ(F²)
_cod_data_source_file            om801092a_si_002.cif
_cod_data_source_block           '_4p'
_cod_original_formula_sum        'C16 H20 O2 '
_cod_database_code               4068785
loop_
_symmetry_equiv_pos_site_id
_symmetry_equiv_pos_as_xyz
1 +X,+Y,+Z
2 1/2-X,1/2+Y,-Z
3 -X,-Y,-Z
4 1/2+X,1/2-Y,+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
O(1) O -0.03253(19) 0.40534(10) 0.15126(16) 0.0483(5) Uani 1.00 1 d .
O(2) O 0.1291(2) 0.33211(9) 0.34009(17) 0.0564(5) Uani 1.00 1 d .
C(1) C 0.1211(2) 0.38320(13) 0.2261(2) 0.0451(7) Uani 1.00 1 d .
C(2) C -0.1065(2) 0.45424(15) 0.2323(2) 0.0562(8) Uani 1.00 1 d .
C(3) C -0.0201(3) 0.53456(14) 0.2771(2) 0.0550(8) Uani 1.00 1 d .
C(4) C 0.1465(2) 0.51615(14) 0.3599(2) 0.0464(7) Uani 1.00 1 d .
C(5) C 0.2242(2) 0.45855(13) 0.2792(2) 0.0390(7) Uani 1.00 1 d .
C(6) C 0.0629(3) 0.25185(15) 0.2986(3) 0.0847(10) Uani 1.00 1 d .
C(7) C 0.1295(3) 0.19267(15) 0.4044(3) 0.0880(11) Uani 1.00 1 d .
C(8) C 0.2608(2) 0.50218(13) 0.1565(2) 0.0385(7) Uani 1.00 1 d .
C(9) C 0.3403(2) 0.44529(15) 0.0858(2) 0.0431(7) Uani 1.00 1 d .
C(10) C 0.4035(3) 0.40056(16) 0.0286(2) 0.0531(8) Uani 1.00 1 d .
C(11) C 0.3571(2) 0.58087(13) 0.2002(2) 0.0345(6) Uani 1.00 1 d .
C(12) C 0.2999(2) 0.65581(13) 0.1413(2) 0.0393(7) Uani 1.00 1 d .
C(13) C 0.3864(2) 0.72761(14) 0.1782(2) 0.0450(7) Uani 1.00 1 d .
C(14) C 0.5316(2) 0.72453(14) 0.2760(2) 0.0439(7) Uani 1.00 1 d .
C(15) C 0.5906(2) 0.64992(14) 0.3359(2) 0.0454(7) Uani 1.00 1 d .
C(16) C 0.5030(2) 0.57865(14) 0.2975(2) 0.0427(7) Uani 1.00 1 d .
H(1) H 0.1629 0.3535 0.1641 0.054 Uiso 1.00 1 c R
H(2) H -0.2097 0.4661 0.1771 0.067 Uiso 1.00 1 c R
H(3) H -0.1080 0.4240 0.3131 0.067 Uiso 1.00 1 c R
H(4) H -0.0227 0.5662 0.1966 0.066 Uiso 1.00 1 c R
H(5) H -0.0678 0.5650 0.3339 0.066 Uiso 1.00 1 c R
H(6) H 0.2024 0.5667 0.3789 0.056 Uiso 1.00 1 c R
H(7) H 0.1486 0.4904 0.4456 0.056 Uiso 1.00 1 c R
H(8) H 0.3190 0.4396 0.3426 0.047 Uiso 1.00 1 c R
H(9) H -0.0456 0.2543 0.2836 0.102 Uiso 1.00 1 c R
H(10) H 0.0822 0.2358 0.2143 0.102 Uiso 1.00 1 c R
H(11) H 0.2182 0.1689 0.3881 0.106 Uiso 1.00 1 c R
H(12) H 0.0559 0.1505 0.4027 0.106 Uiso 1.00 1 c R
H(13) H 0.1588 0.2190 0.4934 0.106 Uiso 1.00 1 c R
H(14) H 0.1652 0.5175 0.0904 0.046 Uiso 1.00 1 c R
H(15) H 0.4546 0.3644 -0.0177 0.064 Uiso 1.00 1 c R
H(16) H 0.1998 0.6583 0.0745 0.047 Uiso 1.00 1 c R
H(17) H 0.3460 0.7789 0.1364 0.054 Uiso 1.00 1 c R
H(18) H 0.5908 0.7737 0.3020 0.053 Uiso 1.00 1 c R
H(19) H 0.6904 0.6474 0.4030 0.055 Uiso 1.00 1 c R
H(20) H 0.5437 0.5273 0.3388 0.051 Uiso 1.00 1 c R
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.003 0.002
;
International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.000 0.000
;
International Tables for Crystallography
(1992, Vol. C, Table 6.1.1.4)
;
O O 0.011 0.006
;
International Tables for Crystallography
(1992, 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
C(1) O(1) C(2) 113.20(16) yes
C(1) O(2) C(6) 112.60(18) yes
O(1) C(1) O(2) 112.5(2) yes
O(1) C(1) C(5) 112.52(17) yes
O(2) C(1) C(5) 108.19(17) yes
O(1) C(2) C(3) 110.5(2) yes
C(2) C(3) C(4) 109.54(18) yes
C(3) C(4) C(5) 111.80(18) yes
C(1) C(5) C(4) 109.6(2) yes
C(1) C(5) C(8) 110.11(17) yes
C(4) C(5) C(8) 112.84(17) yes
O(2) C(6) C(7) 110.3(2) yes
C(5) C(8) C(9) 110.77(18) yes
C(5) C(8) C(11) 113.27(17) yes
C(9) C(8) C(11) 109.6(2) yes
C(8) C(9) C(10) 179.4(2) yes
C(8) C(11) C(12) 120.00(17) yes
C(8) C(11) C(16) 121.34(18) yes
C(12) C(11) C(16) 118.65(19) yes
C(11) C(12) C(13) 120.79(19) yes
C(12) C(13) C(14) 119.9(2) yes
C(13) C(14) C(15) 119.9(2) yes
C(14) C(15) C(16) 119.47(19) yes
C(11) C(16) C(15) 121.2(2) yes
O(1) C(1) H(1) 107.8 no
O(2) C(1) H(1) 107.8 no
C(5) C(1) H(1) 107.8 no
O(1) C(2) H(2) 109.2 no
O(1) C(2) H(3) 109.2 no
C(3) C(2) H(2) 109.2 no
C(3) C(2) H(3) 109.2 no
H(2) C(2) H(3) 109.5 no
C(2) C(3) H(4) 109.5 no
C(2) C(3) H(5) 109.5 no
C(4) C(3) H(4) 109.5 no
C(4) C(3) H(5) 109.5 no
H(4) C(3) H(5) 109.5 no
C(3) C(4) H(6) 108.9 no
C(3) C(4) H(7) 108.9 no
C(5) C(4) H(6) 108.9 no
C(5) C(4) H(7) 108.9 no
H(6) C(4) H(7) 109.5 no
C(1) C(5) H(8) 108.0 no
C(4) C(5) H(8) 108.0 no
C(8) C(5) H(8) 108.0 no
O(2) C(6) H(9) 109.3 no
O(2) C(6) H(10) 109.3 no
C(7) C(6) H(9) 109.3 no
C(7) C(6) H(10) 109.3 no
H(9) C(6) H(10) 109.5 no
C(6) C(7) H(11) 109.5 no
C(6) C(7) H(12) 109.5 no
C(6) C(7) H(13) 109.5 no
H(11) C(7) H(12) 109.5 no
H(11) C(7) H(13) 109.5 no
H(12) C(7) H(13) 109.5 no
C(5) C(8) H(14) 107.7 no
C(9) C(8) H(14) 107.7 no
C(11) C(8) H(14) 107.7 no
C(9) C(10) H(15) 180.0 no
C(11) C(12) H(16) 119.6 no
C(13) C(12) H(16) 119.6 no
C(12) C(13) H(17) 120.0 no
C(14) C(13) H(17) 120.0 no
C(13) C(14) H(18) 120.0 no
C(15) C(14) H(18) 120.0 no
C(14) C(15) H(19) 120.3 no
C(16) C(15) H(19) 120.3 no
C(11) C(16) H(20) 119.4 no
C(15) C(16) H(20) 119.4 no
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
O(1) C(1) 1.412(2) yes
O(1) C(2) 1.437(3) yes
O(2) C(1) 1.394(2) yes
O(2) C(6) 1.436(2) yes
C(1) C(5) 1.528(2) yes
C(2) C(3) 1.512(3) yes
C(3) C(4) 1.515(3) yes
C(4) C(5) 1.537(3) yes
C(5) C(8) 1.540(3) yes
C(6) C(7) 1.419(3) yes
C(8) C(9) 1.476(3) yes
C(8) C(11) 1.529(3) yes
C(9) C(10) 1.175(3) yes
C(11) C(12) 1.378(2) yes
C(11) C(16) 1.384(2) yes
C(12) C(13) 1.386(3) yes
C(13) C(14) 1.382(3) yes
C(14) C(15) 1.380(3) yes
C(15) C(16) 1.385(3) yes
C(1) H(1) 0.950 no
C(2) H(2) 0.950 no
C(2) H(3) 0.950 no
C(3) H(4) 0.950 no
C(3) H(5) 0.950 no
C(4) H(6) 0.950 no
C(4) H(7) 0.950 no
C(5) H(8) 0.950 no
C(6) H(9) 0.950 no
C(6) H(10) 0.950 no
C(7) H(11) 0.950 no
C(7) H(12) 0.950 no
C(7) H(13) 0.950 no
C(8) H(14) 0.950 no
C(10) H(15) 0.950 no
C(12) H(16) 0.950 no
C(13) H(17) 0.950 no
C(14) H(18) 0.950 no
C(15) H(19) 0.950 no
C(16) H(20) 0.950 no
