# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2020

 
data_Compound2d
 
_publ_contact_author_name 
; 
Yasuhide Inokuma
; 
_publ_contact_author_address 
; 
Division of Applied Chemistry, Faculty of Engineering, Hokkaido University,
Kita 13 Nishi 8 Kita-ku, Sapporo, Hokkaido 060-8628, (Japan)

Institute for Chemical Reaction Design and Discovery(WPI-ICRD), Hokkaido University, Kita 21, Nishi 10, Kita-ku, Sapporo 001-0021, (Japan)
; 
_publ_contact_author_email 
'inokuma@eng.hokudai.ac.jp'
  
_publ_contact_author_fax            +81-11-706-6557 
_publ_contact_author_phone          +81-11-706-6556 
_publ_requested_journal             'Organic & Biomolecular Chemistry'            
_publ_section_title 
;
Modular synthesis of aliphatic oligoketones via site-selective silylation of acetylacetone derivatives
;
loop_ 
_publ_author_name 
_publ_author_address 

'Parantap Sarkar' 
; 
Institute for Chemical Reaction Design and Discovery(WPI-ICRD), Hokkaido University, Kita 21, Nishi 10, Kita-ku, Sapporo 001-0021, (Japan).
;
'Yuya Inaba' 
; 
Division of Applied Chemistry, Faculty of Engineering, Hokkaido University,
Kita 13 Nishi 8 Kita-ku, Sapporo, Hokkaido 060-8628, (Japan).
; 
'Hayato Shirakura' 
; 
Division of Applied Chemistry, Faculty of Engineering, Hokkaido University,
Kita 13 Nishi 8 Kita-ku, Sapporo, Hokkaido 060-8628, (Japan).
; 
'Tomoki Yoneda' 
; 
Division of Applied Chemistry, Faculty of Engineering, Hokkaido University,
Kita 13 Nishi 8 Kita-ku, Sapporo, Hokkaido 060-8628, (Japan).
; 
'Yasuhide Inokuma' 
; 
Division of Applied Chemistry, Faculty of Engineering, Hokkaido University,
Kita 13 Nishi 8 Kita-ku, Sapporo, Hokkaido 060-8628, (Japan).

Institute for Chemical Reaction Design and Discovery(WPI-ICRD), Hokkaido University, Kita 21, Nishi 10, Kita-ku, Sapporo 001-0021, (Japan).
;


_publ_section_abstract 
; 
  
; 
_publ_section_references 
; 
   Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122. 
   SHELXT Version 2018/2 
  
   Sheldrick, G.M. (2015) SHELXL Version 2018/3, Acta Cryst. C71, 3-8. 
;

_audit_creation_method            'SHELXL-2018/3'
_shelx_SHELXL_version_number      '2018/3'
_chemical_name_systematic         ?
_chemical_name_common             ?
_chemical_melting_point           ?
_chemical_formula_moiety
 'C22 H28 O2 Si'
_chemical_formula_sum
 'C22 H28 O2 Si' 
_chemical_formula_weight          352.53

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'
 'Si'  'Si'   0.0817   0.0704
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 
_space_group_crystal_system       monoclinic
_space_group_IT_number            5
_space_group_name_H-M_alt         'C 2'
_space_group_name_Hall            'C 2y'
 
_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.
;
 
loop_
 _space_group_symop_operation_xyz
 'x, y, z'
 '-x, y, -z'
 'x+1/2, y+1/2, z'
 '-x+1/2, y+1/2, -z'
 
_cell_length_a                    19.7751(7)
_cell_length_b                    7.6977(3)
_cell_length_c                    13.7091(5)
_cell_angle_alpha                 90
_cell_angle_beta                  104.859(4)
_cell_angle_gamma                 90
_cell_volume                      2017.05(13)
_cell_formula_units_Z             4
_cell_measurement_temperature     123(2)
_cell_measurement_reflns_used   10487
_cell_measurement_theta_min     2.9110
_cell_measurement_theta_max     29.3990
 
_exptl_crystal_description        'plate'
_exptl_crystal_colour             'colorless'
_exptl_crystal_density_meas       ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_density_diffrn     1.161          
_exptl_crystal_F_000              760
_exptl_transmission_factor_min    ?
_exptl_transmission_factor_max    ?
_exptl_crystal_size_max           0.400
_exptl_crystal_size_mid           0.200
_exptl_crystal_size_min           0.060
_exptl_absorpt_coefficient_mu     0.128
_shelx_estimated_absorpt_T_min    0.951
_shelx_estimated_absorpt_T_max    0.992
_exptl_absorpt_correction_T_min                   0.64328
_exptl_absorpt_correction_T_max                   1.00000
_exptl_absorpt_correction_type            multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.43a (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_diffrn_ambient_temperature       123(2)
_diffrn_radiation_wavelength      0.71073
_diffrn_radiation_type            MoK\a
_diffrn_source 'Rotating-anode X-ray tube (dual wavelength)'
_diffrn_source_type 'Rigaku (Mo) X-ray DW Source'
_diffrn_measurement_device 'four-circle diffractometer'
_diffrn_measurement_device_type 'XtaLAB AFC11 (RCD3): quarter-chi single'
_diffrn_measurement_method        ?
_diffrn_detector 'CCD plate'
_diffrn_reflns_number             11900
_diffrn_reflns_av_unetI/netI      0.0238
_diffrn_reflns_av_R_equivalents   0.0261
_diffrn_reflns_limit_h_min        -23
_diffrn_reflns_limit_h_max        23
_diffrn_reflns_limit_k_min        -7
_diffrn_reflns_limit_k_max        9
_diffrn_reflns_limit_l_min        -16
_diffrn_reflns_limit_l_max        16
_diffrn_reflns_theta_min          2.286
_diffrn_reflns_theta_max          24.998
_diffrn_reflns_theta_full         24.998
_diffrn_measured_fraction_theta_max   0.999
_diffrn_measured_fraction_theta_full  0.999
_diffrn_reflns_Laue_measured_fraction_max    0.999
_diffrn_reflns_Laue_measured_fraction_full   0.999
_diffrn_reflns_point_group_measured_fraction_max   0.933
_diffrn_reflns_point_group_measured_fraction_full  0.933
_reflns_number_total              3316
_reflns_number_gt                 3240
_reflns_threshold_expression      'I > 2σ(I)'
_reflns_Friedel_coverage          0.727
_reflns_Friedel_fraction_max      0.856
_reflns_Friedel_fraction_full     0.856
 
_reflns_special_details
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
 
_computing_data_collection        'CrysAlisPro 1.171.39.43a (Rigaku OD, 2018)'
_computing_cell_refinement        'CrysAlisPro 1.171.39.43a (Rigaku OD, 2018)'
_computing_data_reduction         'CrysAlisPro 1.171.39.43a (Rigaku OD, 2018)'
_computing_structure_solution     'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement   'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics     'Yadokari-XG 2009 (Wakita Nemoto et al., 2009)'
_computing_publication_material   'Yadokari-XG 2009 (Wakita Nemoto et al., 2009)'
_refine_special_details           ?
_refine_ls_structure_factor_coef  Fsqd
_refine_ls_matrix_type            full
_refine_ls_weighting_scheme       calc
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0368P)²+0.8980P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary      ?
_atom_sites_solution_secondary    ?
_atom_sites_solution_hydrogens    geom
_refine_ls_hydrogen_treatment     constr
_refine_ls_extinction_method      none
_refine_ls_extinction_coef        '.'
_refine_ls_abs_structure_details
;
 Flack x determined using 1352 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack    0.36(4)
_chemical_absolute_configuration  '.'
_refine_ls_number_reflns          3316
_refine_ls_number_parameters      230
_refine_ls_number_restraints      1
_refine_ls_R_factor_all           0.0275
_refine_ls_R_factor_gt            0.0268
_refine_ls_wR_factor_ref          0.0720
_refine_ls_wR_factor_gt           0.0715
_refine_ls_goodness_of_fit_ref    1.082
_refine_ls_restrained_S_all       1.081
_refine_ls_shift/su_max           0.001
_refine_ls_shift/su_mean          0.000
 
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 0.53714(10) 0.6951(3) 0.19973(14) 0.0244(5) Uani 1 1 d . . . . .
H1 H 0.523401 0.711438 0.128687 0.029 Uiso 1 1 calc R U . . .
H2 H 0.504090 0.710775 0.238509 0.029 Uiso 1 1 calc R U . . .
C2 C 0.60205(9) 0.6508(3) 0.24450(13) 0.0184(4) Uani 1 1 d . . . . .
C3 C 0.63238(10) 0.6130(3) 0.35566(13) 0.0178(4) Uani 1 1 d . . . . .
C4 C 0.70142(10) 0.7174(3) 0.38659(13) 0.0185(4) Uani 1 1 d . . . . .
C5 C 0.69985(10) 0.9057(3) 0.35576(16) 0.0235(4) Uani 1 1 d . . . . .
H3 H 0.721938 0.976792 0.414609 0.035 Uiso 1 1 calc R U . . .
H4 H 0.651216 0.942833 0.328943 0.035 Uiso 1 1 calc R U . . .
H5 H 0.725363 0.919832 0.303709 0.035 Uiso 1 1 calc R U . . .
O1 O 0.65361(7) 0.62528(19) 0.19413(9) 0.0222(3) Uani 1 1 d . . . . .
O2 O 0.75528(6) 0.6505(2) 0.43383(10) 0.0250(3) Uani 1 1 d . . . . .
Si1 Si 0.65636(3) 0.66878(9) 0.07690(4) 0.02520(16) Uani 1 1 d . . . . .
C6 C 0.60879(13) 0.4958(4) -0.00772(18) 0.0381(6) Uani 1 1 d . . . . .
H6 H 0.631137 0.383380 0.013047 0.057 Uiso 1 1 calc R U . . .
H7 H 0.610029 0.520641 -0.077349 0.057 Uiso 1 1 calc R U . . .
H8 H 0.560074 0.491951 -0.003542 0.057 Uiso 1 1 calc R U . . .
C7 C 0.62080(14) 0.8877(4) 0.0369(2) 0.0433(7) Uani 1 1 d . . . . .
H9 H 0.569936 0.886981 0.027137 0.065 Uiso 1 1 calc R U . . .
H10 H 0.631802 0.919227 -0.026524 0.065 Uiso 1 1 calc R U . . .
H11 H 0.641863 0.972737 0.089124 0.065 Uiso 1 1 calc R U . . .
C8 C 0.75111(11) 0.6609(5) 0.08315(17) 0.0445(7) Uani 1 1 d . . . . .
H12 H 0.775910 0.747774 0.131488 0.067 Uiso 1 1 calc R U . . .
H13 H 0.758092 0.685681 0.016295 0.067 Uiso 1 1 calc R U . . .
H14 H 0.769398 0.545002 0.104970 0.067 Uiso 1 1 calc R U . . .
C9 C 0.64796(10) 0.4151(3) 0.37118(15) 0.0202(4) Uani 1 1 d . . . . .
H15 H 0.685490 0.383877 0.338466 0.024 Uiso 1 1 calc R U . . .
H16 H 0.665753 0.391979 0.444333 0.024 Uiso 1 1 calc R U . . .
C10 C 0.58538(10) 0.2988(3) 0.32944(16) 0.0214(4) Uani 1 1 d . . . . .
C11 C 0.55064(12) 0.2155(3) 0.39205(17) 0.0280(5) Uani 1 1 d . . . . .
H17 H 0.567411 0.228476 0.463083 0.034 Uiso 1 1 calc R U . . .
C12 C 0.49189(13) 0.1136(3) 0.3534(2) 0.0364(6) Uani 1 1 d . . . . .
H18 H 0.468783 0.058718 0.397933 0.044 Uiso 1 1 calc R U . . .
C13 C 0.46702(13) 0.0918(3) 0.2503(2) 0.0381(6) Uani 1 1 d . . . . .
H19 H 0.425989 0.025302 0.223481 0.046 Uiso 1 1 calc R U . . .
C14 C 0.50246(13) 0.1677(4) 0.18701(17) 0.0381(5) Uani 1 1 d . . . . .
H20 H 0.486591 0.150505 0.116181 0.046 Uiso 1 1 calc R U . . .
C15 C 0.56118(13) 0.2691(3) 0.22601(17) 0.0294(5) Uani 1 1 d . . . . .
H21 H 0.585361 0.319257 0.181371 0.035 Uiso 1 1 calc R U . . .
C16 C 0.58215(9) 0.6781(3) 0.41920(13) 0.0201(4) Uani 1 1 d . . . . .
H22 H 0.567642 0.798350 0.398014 0.024 Uiso 1 1 calc R U . . .
H23 H 0.539576 0.604930 0.402611 0.024 Uiso 1 1 calc R U . . .
C17 C 0.61183(9) 0.6768(3) 0.53282(13) 0.0201(4) Uani 1 1 d . . . . .
C18 C 0.59761(11) 0.5417(3) 0.59200(16) 0.0244(5) Uani 1 1 d . . . . .
H24 H 0.569910 0.446485 0.560503 0.029 Uiso 1 1 calc R U . . .
C19 C 0.62322(12) 0.5436(3) 0.69656(17) 0.0311(5) Uani 1 1 d . . . . .
H25 H 0.613024 0.450198 0.735817 0.037 Uiso 1 1 calc R U . . .
C20 C 0.66347(11) 0.6814(4) 0.74301(15) 0.0342(6) Uani 1 1 d . . . . .
H26 H 0.681410 0.682654 0.814270 0.041 Uiso 1 1 calc R U . . .
C21 C 0.67762(12) 0.8178(4) 0.68545(17) 0.0339(6) Uani 1 1 d . . . . .
H27 H 0.705214 0.912872 0.717327 0.041 Uiso 1 1 calc R U . . .
C22 C 0.65162(11) 0.8160(3) 0.58138(16) 0.0277(5) Uani 1 1 d . . . . .
H28 H 0.661081 0.910954 0.542666 0.033 Uiso 1 1 calc R U . . .
 
 
_geom_special_details
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
 
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 C2 1.318(3) . ?
C2 O1 1.384(2) . ?
C2 C3 1.516(2) . ?
C3 C4 1.547(3) . ?
C3 C9 1.559(3) . ?
C3 C16 1.562(3) . ?
C4 O2 1.210(2) . ?
C4 C5 1.508(3) . ?
O1 Si1 1.6561(13) . ?
Si1 C7 1.854(3) . ?
Si1 C8 1.855(2) . ?
Si1 C6 1.856(3) . ?
C9 C10 1.515(3) . ?
C10 C11 1.387(3) . ?
C10 C15 1.394(3) . ?
C11 C12 1.389(3) . ?
C12 C13 1.382(4) . ?
C13 C14 1.378(4) . ?
C14 C15 1.387(3) . ?
C16 C17 1.517(2) . ?
C17 C18 1.391(3) . ?
C17 C22 1.393(3) . ?
C18 C19 1.393(3) . ?
C19 C20 1.380(4) . ?
C20 C21 1.384(4) . ?
C21 C22 1.387(3) . ?
 
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
C1 C2 O1 123.95(17) . . ?
C1 C2 C3 127.21(17) . . ?
O1 C2 C3 108.79(15) . . ?
C2 C3 C4 105.65(15) . . ?
C2 C3 C9 109.77(16) . . ?
C4 C3 C9 109.92(15) . . ?
C2 C3 C16 110.79(15) . . ?
C4 C3 C16 108.86(15) . . ?
C9 C3 C16 111.68(16) . . ?
O2 C4 C5 120.73(18) . . ?
O2 C4 C3 121.29(18) . . ?
C5 C4 C3 117.98(16) . . ?
C2 O1 Si1 131.84(12) . . ?
O1 Si1 C7 111.47(11) . . ?
O1 Si1 C8 103.46(9) . . ?
C7 Si1 C8 110.22(15) . . ?
O1 Si1 C6 108.90(10) . . ?
C7 Si1 C6 112.00(14) . . ?
C8 Si1 C6 110.46(13) . . ?
C10 C9 C3 114.33(16) . . ?
C11 C10 C15 117.3(2) . . ?
C11 C10 C9 121.71(19) . . ?
C15 C10 C9 121.01(19) . . ?
C10 C11 C12 121.6(2) . . ?
C13 C12 C11 120.1(2) . . ?
C14 C13 C12 119.2(2) . . ?
C13 C14 C15 120.4(2) . . ?
C14 C15 C10 121.3(2) . . ?
C17 C16 C3 115.88(14) . . ?
C18 C17 C22 118.02(18) . . ?
C18 C17 C16 121.4(2) . . ?
C22 C17 C16 120.5(2) . . ?
C17 C18 C19 121.2(2) . . ?
C20 C19 C18 119.8(2) . . ?
C19 C20 C21 119.80(19) . . ?
C20 C21 C22 120.2(2) . . ?
C21 C22 C17 120.9(2) . . ?
 
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
C1 C2 C3 C4 -132.3(2) . . . . ?
O1 C2 C3 C4 49.9(2) . . . . ?
C1 C2 C3 C9 109.2(2) . . . . ?
O1 C2 C3 C9 -68.6(2) . . . . ?
C1 C2 C3 C16 -14.5(3) . . . . ?
O1 C2 C3 C16 167.60(16) . . . . ?
C2 C3 C4 O2 -131.60(18) . . . . ?
C9 C3 C4 O2 -13.2(2) . . . . ?
C16 C3 C4 O2 109.4(2) . . . . ?
C2 C3 C4 C5 48.2(2) . . . . ?
C9 C3 C4 C5 166.54(16) . . . . ?
C16 C3 C4 C5 -70.8(2) . . . . ?
C1 C2 O1 Si1 11.1(3) . . . . ?
C3 C2 O1 Si1 -170.94(14) . . . . ?
C2 O1 Si1 C7 44.1(2) . . . . ?
C2 O1 Si1 C8 162.5(2) . . . . ?
C2 O1 Si1 C6 -80.0(2) . . . . ?
C2 C3 C9 C10 -56.0(2) . . . . ?
C4 C3 C9 C10 -171.75(15) . . . . ?
C16 C3 C9 C10 67.3(2) . . . . ?
C3 C9 C10 C11 -105.6(2) . . . . ?
C3 C9 C10 C15 75.5(2) . . . . ?
C15 C10 C11 C12 -3.2(3) . . . . ?
C9 C10 C11 C12 177.9(2) . . . . ?
C10 C11 C12 C13 0.6(3) . . . . ?
C11 C12 C13 C14 2.1(4) . . . . ?
C12 C13 C14 C15 -1.9(4) . . . . ?
C13 C14 C15 C10 -0.8(4) . . . . ?
C11 C10 C15 C14 3.3(3) . . . . ?
C9 C10 C15 C14 -177.7(2) . . . . ?
C2 C3 C16 C17 -169.73(18) . . . . ?
C4 C3 C16 C17 -54.0(2) . . . . ?
C9 C3 C16 C17 67.6(2) . . . . ?
C3 C16 C17 C18 -98.3(2) . . . . ?
C3 C16 C17 C22 84.8(3) . . . . ?
C22 C17 C18 C19 -1.0(3) . . . . ?
C16 C17 C18 C19 -178.05(19) . . . . ?
C17 C18 C19 C20 0.0(3) . . . . ?
C18 C19 C20 C21 0.6(3) . . . . ?
C19 C20 C21 C22 -0.2(4) . . . . ?
C20 C21 C22 C17 -0.9(4) . . . . ?
C18 C17 C22 C21 1.5(3) . . . . ?
C16 C17 C22 C21 178.5(2) . . . . ?
 
_refine_diff_density_max    0.146
_refine_diff_density_min   -0.191
_refine_diff_density_rms    0.035




data_Compound3b

_publ_contact_author_name 
; 
Yasuhide Inokuma
; 
_publ_contact_author_address 
; 
Division of Applied Chemistry, Faculty of Engineering, Hokkaido University,
Kita 13 Nishi 8 Kita-ku, Sapporo, Hokkaido 060-8628, (Japan)

Institute for Chemical Reaction Design and Discovery(WPI-ICRD), Hokkaido University, Kita 21, Nishi 10, Kita-ku, Sapporo 001-0021, (Japan)
; 
_publ_contact_author_email 
'inokuma@eng.hokudai.ac.jp'
  
_publ_contact_author_fax            +81-11-706-6557 
_publ_contact_author_phone          +81-11-706-6556 
_publ_requested_journal             'Organic & Biomolecular Chemistry'            
_publ_section_title 
;
Modular synthesis of aliphatic oligoketones via site-selective silylation of acetylacetone derivatives
;
loop_ 
_publ_author_name 
_publ_author_address 

'Parantap Sarkar' 
; 
Institute for Chemical Reaction Design and Discovery(WPI-ICRD), Hokkaido University, Kita 21, Nishi 10, Kita-ku, Sapporo 001-0021, (Japan).
;
'Yuya Inaba' 
; 
Division of Applied Chemistry, Faculty of Engineering, Hokkaido University,
Kita 13 Nishi 8 Kita-ku, Sapporo, Hokkaido 060-8628, (Japan).
; 
'Hayato Shirakura' 
; 
Division of Applied Chemistry, Faculty of Engineering, Hokkaido University,
Kita 13 Nishi 8 Kita-ku, Sapporo, Hokkaido 060-8628, (Japan).
; 
'Tomoki Yoneda' 
; 
Division of Applied Chemistry, Faculty of Engineering, Hokkaido University,
Kita 13 Nishi 8 Kita-ku, Sapporo, Hokkaido 060-8628, (Japan).
; 
'Yasuhide Inokuma' 
; 
Division of Applied Chemistry, Faculty of Engineering, Hokkaido University,
Kita 13 Nishi 8 Kita-ku, Sapporo, Hokkaido 060-8628, (Japan).

Institute for Chemical Reaction Design and Discovery(WPI-ICRD), Hokkaido University, Kita 21, Nishi 10, Kita-ku, Sapporo 001-0021, (Japan).
;


_publ_section_abstract 
; 
  
; 
_publ_section_references 
; 
   Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122. 
   SHELXT Version 2018/2 
  
   Sheldrick, G.M. (2015) SHELXL Version 2018/3, Acta Cryst. C71, 3-8. 
;
 
_audit_creation_method            'SHELXL-2018/3'
_shelx_SHELXL_version_number      '2018/3'
_chemical_name_systematic         ?
_chemical_name_common             ?
_chemical_melting_point           ?
_chemical_formula_moiety
 'C20 H30 O4'
_chemical_formula_sum
 'C20 H30 O4' 
_chemical_formula_weight          334.44

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'
 
_space_group_crystal_system       monoclinic
_space_group_IT_number            14
_space_group_name_H-M_alt         'P 21/n'
_space_group_name_Hall            '-P 2yn'
 
_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.
;
 
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'
 
_cell_length_a                    9.8166(4)
_cell_length_b                    12.8538(5)
_cell_length_c                    14.9915(7)
_cell_angle_alpha                 90
_cell_angle_beta                  98.444(4)
_cell_angle_gamma                 90
_cell_volume                      1871.13(14)
_cell_formula_units_Z             4
_cell_measurement_temperature     123(2)
_cell_measurement_reflns_used     10446
_cell_measurement_theta_min       2.6020
_cell_measurement_theta_max       29.3310
 
_exptl_crystal_description        'block'
_exptl_crystal_colour             'colorless'
_exptl_crystal_density_meas       ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_density_diffrn     1.187          
_exptl_crystal_F_000              728
_exptl_transmission_factor_min    ?
_exptl_transmission_factor_max    ?
_exptl_crystal_size_max           0.600
_exptl_crystal_size_mid           0.450
_exptl_crystal_size_min           0.320
_exptl_absorpt_coefficient_mu     0.081
_shelx_estimated_absorpt_T_min    0.953
_shelx_estimated_absorpt_T_max    0.975
_exptl_absorpt_correction_T_min   0.64662
_exptl_absorpt_correction_T_max   1.00000
_exptl_absorpt_correction_type    multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.43a (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details    ?
_diffrn_ambient_temperature       123(2)
_diffrn_radiation_wavelength      0.71073
_diffrn_radiation_type            MoK\a
_diffrn_source                    'Rotating-anode X-ray tube (dual wavelength)'
_diffrn_source_type               'Rigaku (Mo) X-ray DW Source'
_diffrn_radiation_probe           x-ray
_diffrn_radiation_monochromator   mirror
_diffrn_measurement_device        'four-circle diffractometer'
_diffrn_measurement_device_type   'XtaLAB AFC11 (RCD3): quarter-chi single'
_diffrn_detector                  'CCD plate'
_diffrn_detector_area_resol_mean  ?
_diffrn_reflns_number             23195
_diffrn_reflns_av_unetI/netI      0.0222
_diffrn_reflns_av_R_equivalents   0.0330
_diffrn_reflns_limit_h_min        -11
_diffrn_reflns_limit_h_max        12
_diffrn_reflns_limit_k_min        -16
_diffrn_reflns_limit_k_max        16
_diffrn_reflns_limit_l_min        -18
_diffrn_reflns_limit_l_max        18
_diffrn_reflns_theta_min          2.332
_diffrn_reflns_theta_max          26.995
_diffrn_reflns_theta_full         25.242
_diffrn_measured_fraction_theta_max   0.996
_diffrn_measured_fraction_theta_full  1.000
_diffrn_reflns_Laue_measured_fraction_max    0.996
_diffrn_reflns_Laue_measured_fraction_full   1.000
_diffrn_reflns_point_group_measured_fraction_max   0.996
_diffrn_reflns_point_group_measured_fraction_full  1.000
_reflns_number_total              4072
_reflns_number_gt                 3605
_reflns_threshold_expression      'I > 2σ(I)'
_reflns_Friedel_coverage          0.000
_reflns_Friedel_fraction_max      .
_reflns_Friedel_fraction_full     .
 
_reflns_special_details
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
 
_computing_data_collection        'CrysAlisPro 1.171.39.43a (Rigaku OD, 2018)'
_computing_cell_refinement        'CrysAlisPro 1.171.39.43a (Rigaku OD, 2018)'
_computing_data_reduction         'CrysAlisPro 1.171.39.43a (Rigaku OD, 2018)'
_computing_structure_solution     'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement   'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics     'Yadokari-XG 2009 (Wakita Nemoto et al., 2009)'
_computing_publication_material   'Yadokari-XG 2009 (Wakita Nemoto et al., 2009)'
_refine_special_details           ?
_refine_ls_structure_factor_coef  Fsqd
_refine_ls_matrix_type            full
_refine_ls_weighting_scheme       calc
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0724P)²+1.2193P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary      ?
_atom_sites_solution_secondary    ?
_atom_sites_solution_hydrogens    geom
_refine_ls_hydrogen_treatment     constr
_refine_ls_extinction_method      none
_refine_ls_extinction_coef        .
_refine_ls_number_reflns          4072
_refine_ls_number_parameters      219
_refine_ls_number_restraints      0
_refine_ls_R_factor_all           0.0619
_refine_ls_R_factor_gt            0.0562
_refine_ls_wR_factor_ref          0.1528
_refine_ls_wR_factor_gt           0.1483
_refine_ls_goodness_of_fit_ref    1.058
_refine_ls_restrained_S_all       1.058
_refine_ls_shift/su_max           0.000
_refine_ls_shift/su_mean          0.000
 
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 0.8836(2) 0.21957(15) 0.40915(14) 0.0395(4) Uani 1 1 d . . . . .
H1 H 0.869710 0.160558 0.367416 0.059 Uiso 1 1 calc R U . . .
H2 H 0.806386 0.223691 0.443686 0.059 Uiso 1 1 calc R U . . .
H3 H 0.969628 0.209969 0.450591 0.059 Uiso 1 1 calc R U . . .
C2 C 0.89136(16) 0.31892(13) 0.35642(11) 0.0265(3) Uani 1 1 d . . . . .
C3 C 0.75572(15) 0.37701(12) 0.32233(10) 0.0220(3) Uani 1 1 d . . . . .
C4 C 0.70414(14) 0.41845(11) 0.40759(10) 0.0211(3) Uani 1 1 d . . . . .
C5 C 0.76914(14) 0.51658(11) 0.44992(10) 0.0213(3) Uani 1 1 d . . . . .
H4 H 0.734386 0.577266 0.412711 0.026 Uiso 1 1 calc R U . . .
H5 H 0.870188 0.513124 0.451379 0.026 Uiso 1 1 calc R U . . .
C6 C 0.73672(15) 0.53094(11) 0.54535(10) 0.0220(3) Uani 1 1 d . . . . .
H6 H 0.772996 0.598871 0.569234 0.026 Uiso 1 1 calc R U . . .
H7 H 0.635649 0.531136 0.544326 0.026 Uiso 1 1 calc R U . . .
C7 C 0.79996(14) 0.44483(12) 0.60642(10) 0.0211(3) Uani 1 1 d . . . . .
C8 C 0.74417(15) 0.42724(12) 0.69620(10) 0.0239(3) Uani 1 1 d . . . . .
C9 C 0.60507(15) 0.37138(12) 0.67055(11) 0.0255(3) Uani 1 1 d . . . . .
C10 C 0.6046(2) 0.26447(14) 0.63075(14) 0.0398(4) Uani 1 1 d . . . . .
H8 H 0.609735 0.212580 0.679026 0.060 Uiso 1 1 calc R U . . .
H9 H 0.684187 0.256626 0.598757 0.060 Uiso 1 1 calc R U . . .
H10 H 0.519626 0.254245 0.588430 0.060 Uiso 1 1 calc R U . . .
C11 C 0.64730(16) 0.30151(13) 0.27415(11) 0.0269(3) Uani 1 1 d . . . . .
H11 H 0.638049 0.241233 0.313930 0.032 Uiso 1 1 calc R U . . .
H12 H 0.557026 0.337156 0.262728 0.032 Uiso 1 1 calc R U . . .
C12 C 0.68553(18) 0.26277(14) 0.18497(11) 0.0319(4) Uani 1 1 d . . . . .
H13 H 0.772503 0.222749 0.196463 0.038 Uiso 1 1 calc R U . . .
H14 H 0.612479 0.215812 0.155565 0.038 Uiso 1 1 calc R U . . .
C13 C 0.70296(19) 0.35377(16) 0.12258(11) 0.0370(4) Uani 1 1 d . . . . .
H15 H 0.613812 0.390255 0.107070 0.044 Uiso 1 1 calc R U . . .
H16 H 0.731083 0.327306 0.066003 0.044 Uiso 1 1 calc R U . . .
C14 C 0.81107(18) 0.43001(14) 0.16718(11) 0.0322(4) Uani 1 1 d . . . . .
H17 H 0.815221 0.490752 0.127072 0.039 Uiso 1 1 calc R U . . .
H18 H 0.902439 0.395847 0.175309 0.039 Uiso 1 1 calc R U . . .
C15 C 0.77955(16) 0.46751(12) 0.25874(11) 0.0259(3) Uani 1 1 d . . . . .
H19 H 0.696374 0.512019 0.249385 0.031 Uiso 1 1 calc R U . . .
H20 H 0.857288 0.510533 0.287782 0.031 Uiso 1 1 calc R U . . .
C16 C 0.72300(19) 0.53226(14) 0.74125(12) 0.0347(4) Uani 1 1 d . . . . .
H21 H 0.807879 0.574367 0.743506 0.042 Uiso 1 1 calc R U . . .
H22 H 0.647317 0.570444 0.704206 0.042 Uiso 1 1 calc R U . . .
C17 C 0.6884(2) 0.51950(18) 0.83718(13) 0.0489(5) Uani 1 1 d . . . . .
H23 H 0.684374 0.588894 0.865329 0.059 Uiso 1 1 calc R U . . .
H24 H 0.596618 0.486694 0.834394 0.059 Uiso 1 1 calc R U . . .
C18 C 0.7952(3) 0.4530(2) 0.89488(14) 0.0644(8) Uani 1 1 d . . . . .
H25 H 0.768575 0.444372 0.955645 0.077 Uiso 1 1 calc R U . . .
H26 H 0.885654 0.488421 0.901737 0.077 Uiso 1 1 calc R U . . .
C19 C 0.8074(2) 0.3456(2) 0.85197(13) 0.0519(6) Uani 1 1 d . . . . .
H27 H 0.878985 0.304334 0.889825 0.062 Uiso 1 1 calc R U . . .
H28 H 0.718775 0.308167 0.848876 0.062 Uiso 1 1 calc R U . . .
C20 C 0.84542(17) 0.35685(17) 0.75695(12) 0.0374(4) Uani 1 1 d . . . . .
H29 H 0.846436 0.287128 0.729005 0.045 Uiso 1 1 calc R U . . .
H30 H 0.939326 0.386324 0.761215 0.045 Uiso 1 1 calc R U . . .
O1 O 1.00077(12) 0.35207(11) 0.34131(9) 0.0386(3) Uani 1 1 d . . . . .
O2 O 0.61465(11) 0.37332(9) 0.43975(8) 0.0300(3) Uani 1 1 d . . . . .
O3 O 0.89059(11) 0.39004(10) 0.58520(8) 0.0300(3) Uani 1 1 d . . . . .
O4 O 0.49835(12) 0.41208(11) 0.68175(10) 0.0405(3) Uani 1 1 d . . . . .
 
 
_geom_special_details
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
 
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 C2 1.510(2) . ?
C2 O1 1.207(2) . ?
C2 C3 1.547(2) . ?
C3 C4 1.537(2) . ?
C3 C11 1.540(2) . ?
C3 C15 1.543(2) . ?
C4 O2 1.2104(18) . ?
C4 C5 1.511(2) . ?
C5 C6 1.522(2) . ?
C6 C7 1.510(2) . ?
C7 O3 1.2132(18) . ?
C7 C8 1.542(2) . ?
C8 C16 1.537(2) . ?
C8 C20 1.539(2) . ?
C8 C9 1.541(2) . ?
C9 O4 1.2045(19) . ?
C9 C10 1.498(2) . ?
C11 C12 1.524(2) . ?
C12 C13 1.523(3) . ?
C13 C14 1.525(3) . ?
C14 C15 1.529(2) . ?
C16 C17 1.534(2) . ?
C17 C18 1.521(4) . ?
C18 C19 1.534(4) . ?
C19 C20 1.531(3) . ?
 
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 C2 C1 120.76(16) . . ?
O1 C2 C3 120.93(15) . . ?
C1 C2 C3 118.31(14) . . ?
C4 C3 C11 108.61(12) . . ?
C4 C3 C15 110.52(12) . . ?
C11 C3 C15 110.02(12) . . ?
C4 C3 C2 105.38(12) . . ?
C11 C3 C2 110.67(13) . . ?
C15 C3 C2 111.52(12) . . ?
O2 C4 C5 121.28(14) . . ?
O2 C4 C3 120.80(13) . . ?
C5 C4 C3 117.92(12) . . ?
C4 C5 C6 111.25(12) . . ?
C7 C6 C5 110.91(12) . . ?
O3 C7 C6 121.22(13) . . ?
O3 C7 C8 120.78(13) . . ?
C6 C7 C8 117.99(12) . . ?
C16 C8 C20 111.93(15) . . ?
C16 C8 C9 110.29(13) . . ?
C20 C8 C9 110.20(13) . . ?
C16 C8 C7 110.06(13) . . ?
C20 C8 C7 108.74(12) . . ?
C9 C8 C7 105.41(12) . . ?
O4 C9 C10 120.14(16) . . ?
O4 C9 C8 121.32(15) . . ?
C10 C9 C8 118.53(14) . . ?
C12 C11 C3 112.03(13) . . ?
C13 C12 C11 110.62(14) . . ?
C12 C13 C14 110.98(14) . . ?
C13 C14 C15 112.14(14) . . ?
C14 C15 C3 112.70(13) . . ?
C17 C16 C8 112.39(15) . . ?
C18 C17 C16 111.36(18) . . ?
C17 C18 C19 110.92(17) . . ?
C20 C19 C18 110.50(18) . . ?
C19 C20 C8 112.42(15) . . ?
 
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
O1 C2 C3 C4 -111.86(16) . . . . ?
C1 C2 C3 C4 68.14(17) . . . . ?
O1 C2 C3 C11 130.92(16) . . . . ?
C1 C2 C3 C11 -49.08(19) . . . . ?
O1 C2 C3 C15 8.1(2) . . . . ?
C1 C2 C3 C15 -171.91(14) . . . . ?
C11 C3 C4 O2 18.80(19) . . . . ?
C15 C3 C4 O2 139.58(14) . . . . ?
C2 C3 C4 O2 -99.82(16) . . . . ?
C11 C3 C4 C5 -161.52(13) . . . . ?
C15 C3 C4 C5 -40.74(17) . . . . ?
C2 C3 C4 C5 79.87(15) . . . . ?
O2 C4 C5 C6 15.1(2) . . . . ?
C3 C4 C5 C6 -164.53(12) . . . . ?
C4 C5 C6 C7 64.42(16) . . . . ?
C5 C6 C7 O3 16.8(2) . . . . ?
C5 C6 C7 C8 -162.15(12) . . . . ?
O3 C7 C8 C16 138.15(16) . . . . ?
C6 C7 C8 C16 -42.85(18) . . . . ?
O3 C7 C8 C20 15.2(2) . . . . ?
C6 C7 C8 C20 -165.78(14) . . . . ?
O3 C7 C8 C9 -102.92(16) . . . . ?
C6 C7 C8 C9 76.08(16) . . . . ?
C16 C8 C9 O4 3.8(2) . . . . ?
C20 C8 C9 O4 127.89(17) . . . . ?
C7 C8 C9 O4 -114.94(17) . . . . ?
C16 C8 C9 C10 -176.34(14) . . . . ?
C20 C8 C9 C10 -52.27(19) . . . . ?
C7 C8 C9 C10 64.89(17) . . . . ?
C4 C3 C11 C12 175.81(13) . . . . ?
C15 C3 C11 C12 54.71(18) . . . . ?
C2 C3 C11 C12 -68.98(17) . . . . ?
C3 C11 C12 C13 -57.95(18) . . . . ?
C11 C12 C13 C14 57.04(19) . . . . ?
C12 C13 C14 C15 -54.7(2) . . . . ?
C13 C14 C15 C3 52.70(19) . . . . ?
C4 C3 C15 C14 -171.82(13) . . . . ?
C11 C3 C15 C14 -51.88(17) . . . . ?
C2 C3 C15 C14 71.31(16) . . . . ?
C20 C8 C16 C17 -50.39(19) . . . . ?
C9 C8 C16 C17 72.68(19) . . . . ?
C7 C8 C16 C17 -171.43(14) . . . . ?
C8 C16 C17 C18 53.8(2) . . . . ?
C16 C17 C18 C19 -57.4(2) . . . . ?
C17 C18 C19 C20 57.9(2) . . . . ?
C18 C19 C20 C8 -54.9(2) . . . . ?
C16 C8 C20 C19 51.3(2) . . . . ?
C9 C8 C20 C19 -71.8(2) . . . . ?
C7 C8 C20 C19 173.14(16) . . . . ?
 
_refine_diff_density_max    0.539
_refine_diff_density_min   -0.318
_refine_diff_density_rms    0.051




 
data_Compound5a

_publ_contact_author_name 
; 
Yasuhide Inokuma
; 
_publ_contact_author_address 
; 
Division of Applied Chemistry, Faculty of Engineering, Hokkaido University,
Kita 13 Nishi 8 Kita-ku, Sapporo, Hokkaido 060-8628, (Japan)

Institute for Chemical Reaction Design and Discovery(WPI-ICRD), Hokkaido University, Kita 21, Nishi 10, Kita-ku, Sapporo 001-0021, (Japan)
; 
_publ_contact_author_email 
'inokuma@eng.hokudai.ac.jp'
  
_publ_contact_author_fax            +81-11-706-6557 
_publ_contact_author_phone          +81-11-706-6556 
_publ_requested_journal             'Organic & Biomolecular Chemistry'            
_publ_section_title 
;
Modular synthesis of aliphatic oligoketones via site-selective silylation of acetylacetone derivatives
;
loop_ 
_publ_author_name 
_publ_author_address 

'Parantap Sarkar' 
; 
Institute for Chemical Reaction Design and Discovery(WPI-ICRD), Hokkaido University, Kita 21, Nishi 10, Kita-ku, Sapporo 001-0021, (Japan).
;
'Yuya Inaba' 
; 
Division of Applied Chemistry, Faculty of Engineering, Hokkaido University,
Kita 13 Nishi 8 Kita-ku, Sapporo, Hokkaido 060-8628, (Japan).
; 
'Hayato Shirakura' 
; 
Division of Applied Chemistry, Faculty of Engineering, Hokkaido University,
Kita 13 Nishi 8 Kita-ku, Sapporo, Hokkaido 060-8628, (Japan).
; 
'Tomoki Yoneda' 
; 
Division of Applied Chemistry, Faculty of Engineering, Hokkaido University,
Kita 13 Nishi 8 Kita-ku, Sapporo, Hokkaido 060-8628, (Japan).
; 
'Yasuhide Inokuma' 
; 
Division of Applied Chemistry, Faculty of Engineering, Hokkaido University,
Kita 13 Nishi 8 Kita-ku, Sapporo, Hokkaido 060-8628, (Japan).

Institute for Chemical Reaction Design and Discovery(WPI-ICRD), Hokkaido University, Kita 21, Nishi 10, Kita-ku, Sapporo 001-0021, (Japan).
;


_publ_section_abstract 
; 
  
; 
_publ_section_references 
; 
   Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122. 
   SHELXT Version 2018/2 
  
   Sheldrick, G.M. (2015) SHELXL Version 2018/3, Acta Cryst. C71, 3-8. 
;
_audit_creation_method            'SHELXL-2017/1'
_shelx_SHELXL_version_number      '2017/1'
_chemical_name_systematic         ?
_chemical_name_common             ?
_chemical_melting_point           ?
_chemical_formula_moiety  
'C20 H38 O4 Si2'
_chemical_formula_sum
 'C10 H19 O2 Si' 
_chemical_formula_weight          199.34

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'
 'Si'  'Si'   0.0817   0.0704
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 
_space_group_crystal_system       monoclinic
_space_group_IT_number            14
_space_group_name_H-M_alt         'P 21/c'
_space_group_name_Hall            '-P 2ybc'
 
_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.
;
 
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'
 
_cell_length_a                    7.1033(14)
_cell_length_b                    15.700(3)
_cell_length_c                    10.748(2)
_cell_angle_alpha                 90
_cell_angle_beta                  90.224(6)
_cell_angle_gamma                 90
_cell_volume                      1198.7(4)
_cell_formula_units_Z             4
_cell_measurement_temperature     123(2)
_cell_measurement_reflns_used     7967
_cell_measurement_theta_min       1.89
_cell_measurement_theta_max       27.51
 
_exptl_crystal_description        'block'
_exptl_crystal_colour             'colourless'
_exptl_crystal_density_meas       ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_density_diffrn     1.105          
_exptl_crystal_F_000              436
_exptl_transmission_factor_min    ?
_exptl_transmission_factor_max    ?
_exptl_crystal_size_max           0.320
_exptl_crystal_size_mid           0.260
_exptl_crystal_size_min           0.090
_exptl_absorpt_coefficient_mu     0.167
_shelx_estimated_absorpt_T_min    0.948
_shelx_estimated_absorpt_T_max    0.985
_exptl_absorpt_correction_type    multi-scan
_exptl_absorpt_correction_T_min   0.1822
_exptl_absorpt_correction_T_max   0.9936
_exptl_absorpt_process_details    'ABSCOR(Rigaku, 1995)'
_exptl_absorpt_special_details    ?
_diffrn_ambient_temperature       123(2)
_diffrn_detector                  'Image Plate'
_diffrn_detector_area_resol_mean  10
_diffrn_detector_type             'Rigaku IP'
_diffrn_measurement_device        'four-circle diffractometer'
_diffrn_measurement_device_type   RAPID
_diffrn_measurement_method        'ω scans'
_diffrn_radiation_monochromator   graphite
_diffrn_radiation_probe           x-ray
_diffrn_radiation_type            MoK\a
_diffrn_radiation_wavelength      0.71075
_diffrn_source                    'sealed X-ray tube'
_diffrn_reflns_number             10679
_diffrn_reflns_av_unetI/netI      0.0663
_diffrn_reflns_av_R_equivalents   0.0703
_diffrn_reflns_limit_h_min        -9
_diffrn_reflns_limit_h_max        9
_diffrn_reflns_limit_k_min        -20
_diffrn_reflns_limit_k_max        20
_diffrn_reflns_limit_l_min        -13
_diffrn_reflns_limit_l_max        13
_diffrn_reflns_theta_min          1.895
_diffrn_reflns_theta_max          27.483
_diffrn_reflns_theta_full         25.242
_diffrn_measured_fraction_theta_max   0.998
_diffrn_measured_fraction_theta_full  1.000
_diffrn_reflns_Laue_measured_fraction_max    0.998
_diffrn_reflns_Laue_measured_fraction_full   1.000
_diffrn_reflns_point_group_measured_fraction_max   0.998
_diffrn_reflns_point_group_measured_fraction_full  1.000
_reflns_number_total              2726
_reflns_number_gt                 2002
_reflns_threshold_expression      'I > 2σ(I)'
_reflns_Friedel_coverage          0.000
_reflns_Friedel_fraction_max      .
_reflns_Friedel_fraction_full     .
 
_reflns_special_details
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
 
_computing_data_collection        ?
_computing_cell_refinement        ?
_computing_data_reduction         ?
_computing_structure_solution     ?
_computing_structure_refinement 'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_molecular_graphics     ?
_computing_publication_material   ?
_refine_special_details
;
 Refined as a 2-component twin.
;
_refine_ls_structure_factor_coef  Fsqd
_refine_ls_matrix_type            full
_refine_ls_weighting_scheme       calc
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0924P)²+0.7584P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary      ?
_atom_sites_solution_secondary    ?
_atom_sites_solution_hydrogens    geom
_refine_ls_hydrogen_treatment     constr
_refine_ls_extinction_method      none
_refine_ls_extinction_coef        .
_refine_ls_number_reflns          2726
_refine_ls_number_parameters      124
_refine_ls_number_restraints      0
_refine_ls_R_factor_all           0.0970
_refine_ls_R_factor_gt            0.0694
_refine_ls_wR_factor_ref          0.1941
_refine_ls_wR_factor_gt           0.1738
_refine_ls_goodness_of_fit_ref    1.075
_refine_ls_restrained_S_all       1.075
_refine_ls_shift/su_max           0.000
_refine_ls_shift/su_mean          0.000
 
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
Si2 Si 0.69227(18) 0.60698(6) 0.84204(11) 0.0390(3) Uani 1 1 d . . . . .
O4 O 0.7022(4) 0.50750(15) 0.7872(3) 0.0418(6) Uani 1 1 d . . . . .
O5 O 0.4402(4) 0.36659(19) 0.6216(3) 0.0527(8) Uani 1 1 d . . . . .
C10 C 0.8439(5) 0.4660(2) 0.7269(4) 0.0383(9) Uani 1 1 d . . . . .
C11 C 0.5855(6) 0.4056(2) 0.6023(4) 0.0386(9) Uani 1 1 d . . . . .
C12 C 0.7709(5) 0.3843(2) 0.6701(4) 0.0367(8) Uani 1 1 d . . . . .
C13 C 0.5926(5) 0.4758(2) 0.5056(4) 0.0394(9) Uani 1 1 d . . . . .
H1 H 0.623981 0.450654 0.423833 0.047 Uiso 1 1 calc R U . . .
H2 H 0.693983 0.516363 0.527969 0.047 Uiso 1 1 calc R U . . .
C14 C 0.4440(7) 0.6149(3) 0.8934(4) 0.0504(11) Uani 1 1 d . . . . .
H3 H 0.360234 0.608688 0.821263 0.076 Uiso 1 1 calc R U . . .
H4 H 0.422980 0.670453 0.932370 0.076 Uiso 1 1 calc R U . . .
H5 H 0.417524 0.569597 0.953601 0.076 Uiso 1 1 calc R U . . .
C15 C 0.7444(6) 0.6834(2) 0.7160(4) 0.0482(10) Uani 1 1 d . . . . .
H6 H 0.878322 0.680140 0.694907 0.072 Uiso 1 1 calc R U . . .
H7 H 0.713984 0.741193 0.743675 0.072 Uiso 1 1 calc R U . . .
H8 H 0.668538 0.669245 0.642458 0.072 Uiso 1 1 calc R U . . .
C16 C 0.8536(7) 0.6213(3) 0.9768(4) 0.0567(12) Uani 1 1 d . . . . .
H9 H 0.837798 0.573716 1.034889 0.085 Uiso 1 1 calc R U . . .
H10 H 0.824062 0.674882 1.019106 0.085 Uiso 1 1 calc R U . . .
H11 H 0.984002 0.622722 0.947471 0.085 Uiso 1 1 calc R U . . .
C17 C 0.9049(7) 0.3465(3) 0.5741(4) 0.0484(10) Uani 1 1 d . . . . .
H12 H 0.932496 0.389254 0.510334 0.073 Uiso 1 1 calc R U . . .
H13 H 0.846119 0.296683 0.535110 0.073 Uiso 1 1 calc R U . . .
H14 H 1.022243 0.329253 0.615297 0.073 Uiso 1 1 calc R U . . .
C18 C 1.0206(6) 0.4933(3) 0.7226(4) 0.0480(10) Uani 1 1 d . . . . .
H15 H 1.054951 0.544742 0.763256 0.058 Uiso 1 1 calc R U . . .
H16 H 1.112656 0.461331 0.678928 0.058 Uiso 1 1 calc R U . . .
C19 C 0.7342(6) 0.3203(2) 0.7747(4) 0.0452(10) Uani 1 1 d . . . . .
H17 H 0.851025 0.310324 0.821317 0.068 Uiso 1 1 calc R U . . .
H18 H 0.689902 0.266423 0.738939 0.068 Uiso 1 1 calc R U . . .
H19 H 0.638199 0.343044 0.830860 0.068 Uiso 1 1 calc R U . . .
 
 
_geom_special_details
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
 
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
Si2 O4 1.671(3) . ?
Si2 C15 1.848(4) . ?
Si2 C14 1.854(5) . ?
Si2 C16 1.857(5) . ?
O4 C10 1.365(5) . ?
O5 C11 1.219(5) . ?
C10 C18 1.326(6) . ?
C10 C12 1.512(5) . ?
C11 C13 1.516(5) . ?
C11 C12 1.540(5) . ?
C12 C17 1.527(5) . ?
C12 C19 1.531(5) . ?
C13 C13 1.522(7) 3_666 ?
C13 H1 0.9900 . ?
C13 H2 0.9900 . ?
C14 H3 0.9800 . ?
C14 H4 0.9800 . ?
C14 H5 0.9800 . ?
C15 H6 0.9800 . ?
C15 H7 0.9800 . ?
C15 H8 0.9800 . ?
C16 H9 0.9800 . ?
C16 H10 0.9800 . ?
C16 H11 0.9800 . ?
C17 H12 0.9800 . ?
C17 H13 0.9800 . ?
C17 H14 0.9800 . ?
C18 H15 0.9500 . ?
C18 H16 0.9500 . ?
C19 H17 0.9800 . ?
C19 H18 0.9800 . ?
C19 H19 0.9800 . ?
 
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
O4 Si2 C15 109.80(17) . . ?
O4 Si2 C14 102.06(18) . . ?
C15 Si2 C14 111.6(2) . . ?
O4 Si2 C16 111.19(18) . . ?
C15 Si2 C16 111.6(2) . . ?
C14 Si2 C16 110.2(2) . . ?
C10 O4 Si2 130.2(2) . . ?
C18 C10 O4 124.2(4) . . ?
C18 C10 C12 125.7(4) . . ?
O4 C10 C12 110.1(3) . . ?
O5 C11 C13 120.9(4) . . ?
O5 C11 C12 122.2(3) . . ?
C13 C11 C12 116.9(3) . . ?
C10 C12 C17 112.9(3) . . ?
C10 C12 C19 108.7(3) . . ?
C17 C12 C19 110.5(3) . . ?
C10 C12 C11 107.3(3) . . ?
C17 C12 C11 107.4(3) . . ?
C19 C12 C11 110.0(3) . . ?
C11 C13 C13 112.7(4) . 3_666 ?
C11 C13 H1 109.1 . . ?
C13 C13 H1 109.1 3_666 . ?
C11 C13 H2 109.1 . . ?
C13 C13 H2 109.1 3_666 . ?
H1 C13 H2 107.8 . . ?
Si2 C14 H3 109.5 . . ?
Si2 C14 H4 109.5 . . ?
H3 C14 H4 109.5 . . ?
Si2 C14 H5 109.5 . . ?
H3 C14 H5 109.5 . . ?
H4 C14 H5 109.5 . . ?
Si2 C15 H6 109.5 . . ?
Si2 C15 H7 109.5 . . ?
H6 C15 H7 109.5 . . ?
Si2 C15 H8 109.5 . . ?
H6 C15 H8 109.5 . . ?
H7 C15 H8 109.5 . . ?
Si2 C16 H9 109.5 . . ?
Si2 C16 H10 109.5 . . ?
H9 C16 H10 109.5 . . ?
Si2 C16 H11 109.5 . . ?
H9 C16 H11 109.5 . . ?
H10 C16 H11 109.5 . . ?
C12 C17 H12 109.5 . . ?
C12 C17 H13 109.5 . . ?
H12 C17 H13 109.5 . . ?
C12 C17 H14 109.5 . . ?
H12 C17 H14 109.5 . . ?
H13 C17 H14 109.5 . . ?
C10 C18 H15 120.0 . . ?
C10 C18 H16 120.0 . . ?
H15 C18 H16 120.0 . . ?
C12 C19 H17 109.5 . . ?
C12 C19 H18 109.5 . . ?
H17 C19 H18 109.5 . . ?
C12 C19 H19 109.5 . . ?
H17 C19 H19 109.5 . . ?
H18 C19 H19 109.5 . . ?
 
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
C15 Si2 O4 C10 55.4(4) . . . . ?
C14 Si2 O4 C10 173.9(3) . . . . ?
C16 Si2 O4 C10 -68.6(4) . . . . ?
Si2 O4 C10 C18 14.7(6) . . . . ?
Si2 O4 C10 C12 -167.1(3) . . . . ?
C18 C10 C12 C17 -16.8(6) . . . . ?
O4 C10 C12 C17 165.0(3) . . . . ?
C18 C10 C12 C19 106.1(5) . . . . ?
O4 C10 C12 C19 -72.1(4) . . . . ?
C18 C10 C12 C11 -134.9(4) . . . . ?
O4 C10 C12 C11 46.9(4) . . . . ?
O5 C11 C12 C10 -127.3(4) . . . . ?
C13 C11 C12 C10 55.1(4) . . . . ?
O5 C11 C12 C17 111.1(4) . . . . ?
C13 C11 C12 C17 -66.5(4) . . . . ?
O5 C11 C12 C19 -9.2(5) . . . . ?
C13 C11 C12 C19 173.2(3) . . . . ?
O5 C11 C13 C13 32.9(6) . . . 3_666 ?
C12 C11 C13 C13 -149.4(4) . . . 3_666 ?
 
_refine_diff_density_max    0.482
_refine_diff_density_min   -0.471
_refine_diff_density_rms    0.062




 
data_Compound7
 
_publ_contact_author_name 
; 
Yasuhide Inokuma
; 
_publ_contact_author_address 
; 
Division of Applied Chemistry, Faculty of Engineering, Hokkaido University,
Kita 13 Nishi 8 Kita-ku, Sapporo, Hokkaido 060-8628, (Japan)

Institute for Chemical Reaction Design and Discovery(WPI-ICRD), Hokkaido University, Kita 21, Nishi 10, Kita-ku, Sapporo 001-0021, (Japan)
; 
_publ_contact_author_email 
'inokuma@eng.hokudai.ac.jp'
  
_publ_contact_author_fax            +81-11-706-6557 
_publ_contact_author_phone          +81-11-706-6556 
_publ_requested_journal             'Organic & Biomolecular Chemistry'            
_publ_section_title 
;
Modular synthesis of aliphatic oligoketones via site-selective silylation of acetylacetone derivatives
;
loop_ 
_publ_author_name 
_publ_author_address 

'Parantap Sarkar' 
; 
Institute for Chemical Reaction Design and Discovery(WPI-ICRD), Hokkaido University, Kita 21, Nishi 10, Kita-ku, Sapporo 001-0021, (Japan).
;
'Yuya Inaba' 
; 
Division of Applied Chemistry, Faculty of Engineering, Hokkaido University,
Kita 13 Nishi 8 Kita-ku, Sapporo, Hokkaido 060-8628, (Japan).
; 
'Hayato Shirakura' 
; 
Division of Applied Chemistry, Faculty of Engineering, Hokkaido University,
Kita 13 Nishi 8 Kita-ku, Sapporo, Hokkaido 060-8628, (Japan).
; 
'Tomoki Yoneda' 
; 
Division of Applied Chemistry, Faculty of Engineering, Hokkaido University,
Kita 13 Nishi 8 Kita-ku, Sapporo, Hokkaido 060-8628, (Japan).
; 
'Yasuhide Inokuma' 
; 
Division of Applied Chemistry, Faculty of Engineering, Hokkaido University,
Kita 13 Nishi 8 Kita-ku, Sapporo, Hokkaido 060-8628, (Japan).

Institute for Chemical Reaction Design and Discovery(WPI-ICRD), Hokkaido University, Kita 21, Nishi 10, Kita-ku, Sapporo 001-0021, (Japan).
;


_publ_section_abstract 
; 
  
; 
_publ_section_references 
; 
   Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122. 
   SHELXT Version 2018/2 
  
   Sheldrick, G.M. (2015) SHELXL Version 2018/3, Acta Cryst. C71, 3-8. 
;
_audit_creation_method            'SHELXL-2018/3'
_shelx_SHELXL_version_number      '2018/3'
_chemical_name_systematic         ?
_chemical_name_common             ?
_chemical_melting_point           ?
_chemical_formula_moiety
 'C34 H50 O8'
_chemical_formula_sum
 'C34 H50 O8' 
_chemical_formula_weight          586.74

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'
 
_space_group_crystal_system       triclinic
_space_group_IT_number            2
_space_group_name_H-M_alt         'P -1'
_space_group_name_Hall            '-P 1'
 
_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.
;
 
loop_
 _space_group_symop_operation_xyz
 'x, y, z'
 '-x, -y, -z'
 
_cell_length_a                    7.0479(2)
_cell_length_b                    10.1584(4)
_cell_length_c                    11.6894(4)
_cell_angle_alpha                 91.402(3)
_cell_angle_beta                  99.676(3)
_cell_angle_gamma                 96.997(3)
_cell_volume                      817.99(5)
_cell_formula_units_Z             1
_cell_measurement_temperature     123(2)
_cell_measurement_reflns_used     5315
_cell_measurement_theta_min       2.8000
_cell_measurement_theta_max       29.4750
 
_exptl_crystal_description        'plate'
_exptl_crystal_colour             'colorless'
_exptl_crystal_density_meas       ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_density_diffrn     1.191          
_exptl_crystal_F_000              318
_exptl_transmission_factor_min    ?
_exptl_transmission_factor_max    ?
_exptl_crystal_size_max           0.580
_exptl_crystal_size_mid           0.120
_exptl_crystal_size_min           0.030
_exptl_absorpt_coefficient_mu     0.083
_shelx_estimated_absorpt_T_min    0.953
_shelx_estimated_absorpt_T_max    0.998
_exptl_absorpt_correction_T_min   0.50466
_exptl_absorpt_correction_T_max   1.00000
_exptl_absorpt_correction_type    multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.43a (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details    ?
_diffrn_ambient_temperature       123(2)
_diffrn_radiation_wavelength      0.71073
_diffrn_radiation_type            MoK\a
_diffrn_source         'Rotating-anode X-ray tube (dual wavelength)'
_diffrn_source_type               'Rigaku (Mo) X-ray DW Source'
_diffrn_radiation_probe           x-ray
_diffrn_radiation_monochromator   mirror
_diffrn_measurement_device        'four-circle diffractometer'
_diffrn_measurement_device_type   'XtaLAB AFC11 (RCD3): quarter-chi single'
_diffrn_detector                  'CCD plate'
_diffrn_measurement_method        ?
_diffrn_detector_area_resol_mean  ?
_diffrn_reflns_number             13970
_diffrn_reflns_av_unetI/netI      0.0300
_diffrn_reflns_av_R_equivalents   0.0324
_diffrn_reflns_limit_h_min        -8
_diffrn_reflns_limit_h_max        8
_diffrn_reflns_limit_k_min        -11
_diffrn_reflns_limit_k_max        12
_diffrn_reflns_limit_l_min        -14
_diffrn_reflns_limit_l_max        14
_diffrn_reflns_theta_min          2.625
_diffrn_reflns_theta_max          26.989
_diffrn_reflns_theta_full         25.242
_diffrn_measured_fraction_theta_max   0.992
_diffrn_measured_fraction_theta_full  0.999
_diffrn_reflns_Laue_measured_fraction_max    0.992
_diffrn_reflns_Laue_measured_fraction_full   0.999
_diffrn_reflns_point_group_measured_fraction_max   0.992
_diffrn_reflns_point_group_measured_fraction_full  0.999
_reflns_number_total              3522
_reflns_number_gt                 2919
_reflns_threshold_expression      'I > 2σ(I)'
_reflns_Friedel_coverage          0.000
_reflns_Friedel_fraction_max      .
_reflns_Friedel_fraction_full     .
 
_reflns_special_details
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
 
_computing_data_collection        'CrysAlisPro 1.171.39.43a (Rigaku OD, 2018)'
_computing_cell_refinement        'CrysAlisPro 1.171.39.43a (Rigaku OD, 2018)'
_computing_data_reduction         'CrysAlisPro 1.171.39.43a (Rigaku OD, 2018)'
_computing_structure_solution     'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement   'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics     ?
_computing_publication_material   ?
_refine_special_details           ?
_refine_ls_structure_factor_coef  Fsqd
_refine_ls_matrix_type            full
_refine_ls_weighting_scheme       calc
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0609P)²+0.2828P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary      ?
_atom_sites_solution_secondary    ?
_atom_sites_solution_hydrogens    geom
_refine_ls_hydrogen_treatment     constr
_refine_ls_extinction_method      none
_refine_ls_extinction_coef        .
_refine_ls_number_reflns          3522
_refine_ls_number_parameters      193
_refine_ls_number_restraints      0
_refine_ls_R_factor_all           0.0556
_refine_ls_R_factor_gt            0.0451
_refine_ls_wR_factor_ref          0.1254
_refine_ls_wR_factor_gt           0.1187
_refine_ls_goodness_of_fit_ref    1.029
_refine_ls_restrained_S_all       1.029
_refine_ls_shift/su_max           0.000
_refine_ls_shift/su_mean          0.000
 
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 0.8797(2) 0.56551(18) 0.33346(18) 0.0487(4) Uani 1 1 d . . . . .
H1 H 0.873923 0.571092 0.416590 0.073 Uiso 1 1 calc R U . . .
H2 H 0.935884 0.651508 0.309847 0.073 Uiso 1 1 calc R U . . .
H3 H 0.960597 0.497336 0.318262 0.073 Uiso 1 1 calc R U . . .
C2 C 0.6795(2) 0.52981(14) 0.26587(13) 0.0333(3) Uani 1 1 d . . . . .
C3 C 0.5615(2) 0.64377(14) 0.22494(12) 0.0291(3) Uani 1 1 d . . . . .
C4 C 0.56149(18) 0.73319(12) 0.33337(11) 0.0241(3) Uani 1 1 d . . . . .
C5 C 0.43225(19) 0.68438(13) 0.41830(11) 0.0249(3) Uani 1 1 d . . . . .
H4 H 0.444498 0.589786 0.432160 0.030 Uiso 1 1 calc R U . . .
H5 H 0.295444 0.690815 0.384233 0.030 Uiso 1 1 calc R U . . .
C6 C 0.48452(19) 0.76443(13) 0.53370(11) 0.0267(3) Uani 1 1 d . . . . .
H6 H 0.486702 0.860052 0.518711 0.032 Uiso 1 1 calc R U . . .
H7 H 0.383007 0.740116 0.581302 0.032 Uiso 1 1 calc R U . . .
C7 C 0.67892(19) 0.74131(13) 0.60113(11) 0.0259(3) Uani 1 1 d . . . . .
C8 C 0.7843(2) 0.84941(14) 0.69184(12) 0.0319(3) Uani 1 1 d . . . . .
C9 C 0.85842(19) 0.96957(13) 0.62578(12) 0.0283(3) Uani 1 1 d . . . . .
C10 C 0.99865(19) 0.94777(12) 0.54538(12) 0.0279(3) Uani 1 1 d . . . . .
H8 H 0.961756 0.858751 0.505914 0.033 Uiso 1 1 calc R U . . .
H9 H 1.130583 0.950240 0.591394 0.033 Uiso 1 1 calc R U . . .
C11 C 0.3553(2) 0.58793(17) 0.16676(14) 0.0406(4) Uani 1 1 d . . . . .
H10 H 0.361645 0.520141 0.105678 0.049 Uiso 1 1 calc R U . . .
H11 H 0.285579 0.544141 0.225181 0.049 Uiso 1 1 calc R U . . .
C12 C 0.2433(3) 0.6970(2) 0.11265(15) 0.0536(5) Uani 1 1 d . . . . .
H12 H 0.112919 0.657125 0.073049 0.064 Uiso 1 1 calc R U . . .
H13 H 0.226173 0.760342 0.174729 0.064 Uiso 1 1 calc R U . . .
C13 C 0.3493(3) 0.7716(2) 0.02536(16) 0.0641(6) Uani 1 1 d . . . . .
H14 H 0.354188 0.710316 -0.040987 0.077 Uiso 1 1 calc R U . . .
H15 H 0.276918 0.844602 -0.004829 0.077 Uiso 1 1 calc R U . . .
C14 C 0.5530(3) 0.82789(19) 0.08044(14) 0.0515(5) Uani 1 1 d . . . . .
H16 H 0.547458 0.897641 0.140000 0.062 Uiso 1 1 calc R U . . .
H17 H 0.620987 0.869670 0.020414 0.062 Uiso 1 1 calc R U . . .
C15 C 0.6671(2) 0.72162(16) 0.13667(13) 0.0393(4) Uani 1 1 d . . . . .
H18 H 0.795746 0.763941 0.176972 0.047 Uiso 1 1 calc R U . . .
H19 H 0.688473 0.658771 0.075428 0.047 Uiso 1 1 calc R U . . .
C16 C 0.9604(3) 0.79877(17) 0.76505(15) 0.0492(5) Uani 1 1 d . . . . .
H20 H 0.915836 0.725653 0.811160 0.074 Uiso 1 1 calc R U . . .
H21 H 1.034364 0.871122 0.817108 0.074 Uiso 1 1 calc R U . . .
H22 H 1.043346 0.767203 0.713629 0.074 Uiso 1 1 calc R U . . .
C17 C 0.6437(3) 0.89128(17) 0.76814(14) 0.0450(4) Uani 1 1 d . . . . .
H23 H 0.537917 0.929113 0.719896 0.068 Uiso 1 1 calc R U . . .
H24 H 0.712905 0.957915 0.827487 0.068 Uiso 1 1 calc R U . . .
H25 H 0.590082 0.813615 0.805902 0.068 Uiso 1 1 calc R U . . .
O1 O 0.61286(19) 0.41526(11) 0.24247(12) 0.0519(3) Uani 1 1 d . . . . .
O2 O 0.66581(14) 0.83784(10) 0.35137(8) 0.0313(2) Uani 1 1 d . . . . .
O3 O 0.74949(14) 0.64116(9) 0.58456(9) 0.0334(2) Uani 1 1 d . . . . .
O4 O 0.80932(17) 1.07757(10) 0.64162(10) 0.0407(3) Uani 1 1 d . . . . .
 
 
_geom_special_details
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
 
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 C2 1.494(2) . ?
C2 O1 1.2073(18) . ?
C2 C3 1.546(2) . ?
C3 C11 1.531(2) . ?
C3 C4 1.5412(18) . ?
C3 C15 1.549(2) . ?
C4 O2 1.2090(16) . ?
C4 C5 1.5097(17) . ?
C5 C6 1.5241(18) . ?
C6 C7 1.5094(19) . ?
C7 O3 1.2108(17) . ?
C7 C8 1.5368(19) . ?
C8 C17 1.530(2) . ?
C8 C16 1.535(2) . ?
C8 C9 1.5444(19) . ?
C9 O4 1.2090(17) . ?
C9 C10 1.505(2) . ?
C10 C10 1.520(3) 2_776 ?
C11 C12 1.527(3) . ?
C12 C13 1.526(3) . ?
C13 C14 1.508(3) . ?
C14 C15 1.521(2) . ?
 
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 C2 C1 120.95(15) . . ?
O1 C2 C3 120.92(14) . . ?
C1 C2 C3 118.12(13) . . ?
C11 C3 C4 111.76(11) . . ?
C11 C3 C2 110.42(12) . . ?
C4 C3 C2 106.82(11) . . ?
C11 C3 C15 109.86(13) . . ?
C4 C3 C15 110.39(11) . . ?
C2 C3 C15 107.47(11) . . ?
O2 C4 C5 120.97(12) . . ?
O2 C4 C3 120.90(12) . . ?
C5 C4 C3 118.10(11) . . ?
C4 C5 C6 111.80(10) . . ?
C7 C6 C5 112.62(11) . . ?
O3 C7 C6 121.28(12) . . ?
O3 C7 C8 121.08(12) . . ?
C6 C7 C8 117.65(11) . . ?
C17 C8 C16 111.30(14) . . ?
C17 C8 C7 109.90(12) . . ?
C16 C8 C7 110.01(12) . . ?
C17 C8 C9 109.59(12) . . ?
C16 C8 C9 108.24(13) . . ?
C7 C8 C9 107.70(11) . . ?
O4 C9 C10 121.83(12) . . ?
O4 C9 C8 120.63(13) . . ?
C10 C9 C8 117.50(11) . . ?
C9 C10 C10 111.86(14) . 2_776 ?
C12 C11 C3 111.45(14) . . ?
C13 C12 C11 111.39(16) . . ?
C14 C13 C12 111.20(14) . . ?
C13 C14 C15 111.89(16) . . ?
C14 C15 C3 112.34(13) . . ?
 
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
O1 C2 C3 C11 5.91(19) . . . . ?
C1 C2 C3 C11 -175.11(14) . . . . ?
O1 C2 C3 C4 127.63(14) . . . . ?
C1 C2 C3 C4 -53.39(16) . . . . ?
O1 C2 C3 C15 -113.90(15) . . . . ?
C1 C2 C3 C15 65.08(17) . . . . ?
C11 C3 C4 O2 -136.34(14) . . . . ?
C2 C3 C4 O2 102.79(14) . . . . ?
C15 C3 C4 O2 -13.76(18) . . . . ?
C11 C3 C4 C5 45.54(17) . . . . ?
C2 C3 C4 C5 -75.32(14) . . . . ?
C15 C3 C4 C5 168.13(12) . . . . ?
O2 C4 C5 C6 -12.55(18) . . . . ?
C3 C4 C5 C6 165.56(11) . . . . ?
C4 C5 C6 C7 -68.67(14) . . . . ?
C5 C6 C7 O3 -22.93(17) . . . . ?
C5 C6 C7 C8 157.14(11) . . . . ?
O3 C7 C8 C17 -132.31(14) . . . . ?
C6 C7 C8 C17 47.62(16) . . . . ?
O3 C7 C8 C16 -9.43(19) . . . . ?
C6 C7 C8 C16 170.51(13) . . . . ?
O3 C7 C8 C9 108.35(14) . . . . ?
C6 C7 C8 C9 -71.72(15) . . . . ?
C17 C8 C9 O4 2.52(19) . . . . ?
C16 C8 C9 O4 -119.04(16) . . . . ?
C7 C8 C9 O4 122.05(14) . . . . ?
C17 C8 C9 C10 -179.77(12) . . . . ?
C16 C8 C9 C10 58.67(16) . . . . ?
C7 C8 C9 C10 -60.24(15) . . . . ?
O4 C9 C10 C10 -23.8(2) . . . 2_776 ?
C8 C9 C10 C10 158.54(13) . . . 2_776 ?
C4 C3 C11 C12 68.08(16) . . . . ?
C2 C3 C11 C12 -173.17(12) . . . . ?
C15 C3 C11 C12 -54.81(16) . . . . ?
C3 C11 C12 C13 56.67(18) . . . . ?
C11 C12 C13 C14 -56.0(2) . . . . ?
C12 C13 C14 C15 54.7(2) . . . . ?
C13 C14 C15 C3 -54.35(18) . . . . ?
C11 C3 C15 C14 53.81(17) . . . . ?
C4 C3 C15 C14 -69.87(16) . . . . ?
C2 C3 C15 C14 173.99(13) . . . . ?
 
_refine_diff_density_max    0.369
_refine_diff_density_min   -0.252
_refine_diff_density_rms    0.041




 
data_Compound8

_publ_contact_author_name 
; 
Yasuhide Inokuma
; 
_publ_contact_author_address 
; 
Division of Applied Chemistry, Faculty of Engineering, Hokkaido University,
Kita 13 Nishi 8 Kita-ku, Sapporo, Hokkaido 060-8628, (Japan)

Institute for Chemical Reaction Design and Discovery(WPI-ICRD), Hokkaido University, Kita 21, Nishi 10, Kita-ku, Sapporo 001-0021, (Japan)
; 
_publ_contact_author_email 
'inokuma@eng.hokudai.ac.jp'
  
_publ_contact_author_fax            +81-11-706-6557 
_publ_contact_author_phone          +81-11-706-6556 
_publ_requested_journal             'Organic & Biomolecular Chemistry'            
_publ_section_title 
;
Modular synthesis of aliphatic oligoketones via site-selective silylation of acetylacetone derivatives
;
loop_ 
_publ_author_name 
_publ_author_address 

'Parantap Sarkar' 
; 
Institute for Chemical Reaction Design and Discovery(WPI-ICRD), Hokkaido University, Kita 21, Nishi 10, Kita-ku, Sapporo 001-0021, (Japan).
;
'Yuya Inaba' 
; 
Division of Applied Chemistry, Faculty of Engineering, Hokkaido University,
Kita 13 Nishi 8 Kita-ku, Sapporo, Hokkaido 060-8628, (Japan).
; 
'Hayato Shirakura' 
; 
Division of Applied Chemistry, Faculty of Engineering, Hokkaido University,
Kita 13 Nishi 8 Kita-ku, Sapporo, Hokkaido 060-8628, (Japan).
; 
'Tomoki Yoneda' 
; 
Division of Applied Chemistry, Faculty of Engineering, Hokkaido University,
Kita 13 Nishi 8 Kita-ku, Sapporo, Hokkaido 060-8628, (Japan).
; 
'Yasuhide Inokuma' 
; 
Division of Applied Chemistry, Faculty of Engineering, Hokkaido University,
Kita 13 Nishi 8 Kita-ku, Sapporo, Hokkaido 060-8628, (Japan).

Institute for Chemical Reaction Design and Discovery(WPI-ICRD), Hokkaido University, Kita 21, Nishi 10, Kita-ku, Sapporo 001-0021, (Japan).
;


_publ_section_abstract 
; 
  
; 
_publ_section_references 
; 
   Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122. 
   SHELXT Version 2018/2 
  
   Sheldrick, G.M. (2015) SHELXL Version 2018/3, Acta Cryst. C71, 3-8. 
;
 
_audit_creation_method            'SHELXL-2018/3'
_shelx_SHELXL_version_number      '2018/3'
_chemical_name_systematic         ?
_chemical_name_common             ?
_chemical_melting_point           ?
_chemical_formula_moiety
 'C34 H50 O8'
_chemical_formula_sum
 'C34 H50 O8' 
_chemical_formula_weight          586.74

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'
 
_space_group_crystal_system       triclinic
_space_group_IT_number            2
_space_group_name_H-M_alt         'P -1'
_space_group_name_Hall            '-P 1'
 
_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.
;
 
loop_
 _space_group_symop_operation_xyz
 'x, y, z'
 '-x, -y, -z'
 
_cell_length_a                    7.3875(2)
_cell_length_b                    9.2832(3)
_cell_length_c                    11.5913(3)
_cell_angle_alpha                 103.164(3)
_cell_angle_beta                  95.845(2)
_cell_angle_gamma                 95.145(2)
_cell_volume                      764.77(4)
_cell_formula_units_Z             1
_cell_measurement_temperature     123(2)
_cell_measurement_reflns_used     6794
_cell_measurement_theta_min       3.1200
_cell_measurement_theta_max       29.5420
 
_exptl_crystal_description        'plate'
_exptl_crystal_colour             'colorless'
_exptl_crystal_density_meas       ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_density_diffrn     1.274          
_exptl_crystal_F_000              318
_exptl_transmission_factor_min    ?
_exptl_transmission_factor_max    ?
_exptl_crystal_size_max           0.700
_exptl_crystal_size_mid           0.380
_exptl_crystal_size_min           0.040
_exptl_absorpt_coefficient_mu     0.089
_shelx_estimated_absorpt_T_min    0.940
_shelx_estimated_absorpt_T_max    0.996
_exptl_absorpt_correction_T_min   0.76417
_exptl_absorpt_correction_T_max   1.00000
_exptl_absorpt_correction_type    multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.43a (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details    ?
_diffrn_ambient_temperature       123(2)
_diffrn_radiation_wavelength      0.71073
_diffrn_radiation_type            MoK\a
_diffrn_source                    'Rotating-anode X-ray tube (dual wavelength)'
_diffrn_source_type               'Rigaku (Mo) X-ray DW Source'
_diffrn_radiation_probe           x-ray
_diffrn_radiation_monochromator   mirror
_diffrn_measurement_device        'four-circle diffractometer'
_diffrn_measurement_device_type   'XtaLAB AFC11 (RCD3): quarter-chi single'
_diffrn_detector                  'CCD plate'
_diffrn_detector_area_resol_mean  ?
_diffrn_reflns_number             12777
_diffrn_reflns_av_unetI/netI      0.0215
_diffrn_reflns_av_R_equivalents   0.0226
_diffrn_reflns_limit_h_min        -9
_diffrn_reflns_limit_h_max        9
_diffrn_reflns_limit_k_min        -11
_diffrn_reflns_limit_k_max        11
_diffrn_reflns_limit_l_min        -14
_diffrn_reflns_limit_l_max        14
_diffrn_reflns_theta_min          2.269
_diffrn_reflns_theta_max          26.993
_diffrn_reflns_theta_full         25.242
_diffrn_measured_fraction_theta_max   0.993
_diffrn_measured_fraction_theta_full  0.999
_diffrn_reflns_Laue_measured_fraction_max    0.993
_diffrn_reflns_Laue_measured_fraction_full   0.999
_diffrn_reflns_point_group_measured_fraction_max   0.993
_diffrn_reflns_point_group_measured_fraction_full  0.999
_reflns_number_total              3318
_reflns_number_gt                 2958
_reflns_threshold_expression      'I > 2σ(I)'
_reflns_Friedel_coverage          0.000
_reflns_Friedel_fraction_max      .
_reflns_Friedel_fraction_full     .
 
_reflns_special_details
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
 
_computing_data_collection        'CrysAlisPro 1.171.39.43a (Rigaku OD, 2018)'
_computing_cell_refinement        'CrysAlisPro 1.171.39.43a (Rigaku OD, 2018)'
_computing_data_reduction         'CrysAlisPro 1.171.39.43a (Rigaku OD, 2018)'
_computing_structure_solution     'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement   'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics     'Yadokari-XG 2009 (Wakita Nemoto et al., 2009)'
_computing_publication_material   'Yadokari-XG 2009 (Wakita Nemoto et al., 2009)'
_refine_special_details           ?
_refine_ls_structure_factor_coef  Fsqd
_refine_ls_matrix_type            full
_refine_ls_weighting_scheme       calc
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0439P)²+0.2657P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary      ?
_atom_sites_solution_secondary    ?
_atom_sites_solution_hydrogens    geom
_refine_ls_hydrogen_treatment     constr
_refine_ls_extinction_method      none
_refine_ls_extinction_coef        .
_refine_ls_number_reflns          3318
_refine_ls_number_parameters      193
_refine_ls_number_restraints      0
_refine_ls_R_factor_all           0.0397
_refine_ls_R_factor_gt            0.0350
_refine_ls_wR_factor_ref          0.0932
_refine_ls_wR_factor_gt           0.0904
_refine_ls_goodness_of_fit_ref    1.046
_refine_ls_restrained_S_all       1.046
_refine_ls_shift/su_max           0.000
_refine_ls_shift/su_mean          0.000
 
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 0.21412(17) 0.36090(15) 0.83658(13) 0.0317(3) Uani 1 1 d . . . . .
H1 H 0.185827 0.342563 0.913138 0.048 Uiso 1 1 calc R U . . .
H2 H 0.178919 0.269645 0.773426 0.048 Uiso 1 1 calc R U . . .
H3 H 0.145924 0.440381 0.818149 0.048 Uiso 1 1 calc R U . . .
C2 C 0.41582(15) 0.40702(12) 0.84427(10) 0.0196(2) Uani 1 1 d . . . . .
C3 C 0.54179(14) 0.28217(12) 0.81778(9) 0.0174(2) Uani 1 1 d . . . . .
C4 C 0.50253(14) 0.22040(12) 0.68161(9) 0.0165(2) Uani 1 1 d . . . . .
C5 C 0.60140(14) 0.30277(12) 0.60331(9) 0.0177(2) Uani 1 1 d . . . . .
H4 H 0.729439 0.278913 0.604670 0.021 Uiso 1 1 calc R U . . .
H5 H 0.604476 0.411371 0.635825 0.021 Uiso 1 1 calc R U . . .
C6 C 0.50869(14) 0.26136(12) 0.47512(9) 0.0179(2) Uani 1 1 d . . . . .
H6 H 0.583547 0.309464 0.425110 0.022 Uiso 1 1 calc R U . . .
H7 H 0.500044 0.152161 0.443635 0.022 Uiso 1 1 calc R U . . .
C7 C 0.31839(14) 0.31034(11) 0.46764(9) 0.0155(2) Uani 1 1 d . . . . .
C8 C 0.17831(14) 0.23004(11) 0.35915(9) 0.0144(2) Uani 1 1 d . . . . .
C9 C 0.12351(13) 0.07659(11) 0.38424(9) 0.0145(2) Uani 1 1 d . . . . .
C10 C 0.00084(14) 0.07232(11) 0.47988(9) 0.0155(2) Uani 1 1 d . . . . .
H8 H -0.125479 0.084225 0.448925 0.019 Uiso 1 1 calc R U . . .
H9 H 0.043372 0.156861 0.549394 0.019 Uiso 1 1 calc R U . . .
C11 C 0.74197(15) 0.34723(13) 0.85715(10) 0.0222(2) Uani 1 1 d . . . . .
H10 H 0.762527 0.382463 0.944323 0.033 Uiso 1 1 calc R U . . .
H11 H 0.770018 0.430737 0.820711 0.033 Uiso 1 1 calc R U . . .
H12 H 0.821708 0.270202 0.831647 0.033 Uiso 1 1 calc R U . . .
C12 C 0.49071(17) 0.16054(13) 0.88303(10) 0.0240(2) Uani 1 1 d . . . . .
H13 H 0.575435 0.084764 0.869189 0.036 Uiso 1 1 calc R U . . .
H14 H 0.365291 0.114235 0.852671 0.036 Uiso 1 1 calc R U . . .
H15 H 0.498826 0.205048 0.968871 0.036 Uiso 1 1 calc R U . . .
C13 C 0.01193(14) 0.31830(12) 0.35207(10) 0.0173(2) Uani 1 1 d . . . . .
H16 H -0.048266 0.324129 0.425238 0.021 Uiso 1 1 calc R U . . .
H17 H 0.054418 0.421111 0.348208 0.021 Uiso 1 1 calc R U . . .
C14 C -0.12677(16) 0.24528(13) 0.24271(10) 0.0229(2) Uani 1 1 d . . . . .
H18 H -0.178306 0.146171 0.250310 0.027 Uiso 1 1 calc R U . . .
H19 H -0.228698 0.307060 0.238916 0.027 Uiso 1 1 calc R U . . .
C15 C -0.03768(18) 0.22768(14) 0.12775(11) 0.0269(3) Uani 1 1 d . . . . .
H20 H -0.128577 0.174636 0.059087 0.032 Uiso 1 1 calc R U . . .
H21 H 0.001394 0.327372 0.115520 0.032 Uiso 1 1 calc R U . . .
C16 C 0.12759(17) 0.14128(13) 0.13251(10) 0.0236(2) Uani 1 1 d . . . . .
H22 H 0.187526 0.138690 0.059581 0.028 Uiso 1 1 calc R U . . .
H23 H 0.085853 0.037372 0.133821 0.028 Uiso 1 1 calc R U . . .
C17 C 0.26712(15) 0.21105(12) 0.24267(9) 0.0184(2) Uani 1 1 d . . . . .
H24 H 0.321823 0.309584 0.235766 0.022 Uiso 1 1 calc R U . . .
H25 H 0.366819 0.147005 0.245782 0.022 Uiso 1 1 calc R U . . .
O1 O 0.47829(12) 0.53650(9) 0.86985(8) 0.0271(2) Uani 1 1 d . . . . .
O2 O 0.39003(11) 0.11313(9) 0.63852(7) 0.02262(19) Uani 1 1 d . . . . .
O3 O 0.27657(11) 0.40836(9) 0.54526(7) 0.02336(19) Uani 1 1 d . . . . .
O4 O 0.17989(11) -0.03465(8) 0.33041(7) 0.02153(18) Uani 1 1 d . . . . .
 
 
_geom_special_details
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
 
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 C2 1.5009(16) . ?
C2 O1 1.2066(14) . ?
C2 C3 1.5470(15) . ?
C3 C11 1.5287(15) . ?
C3 C12 1.5362(15) . ?
C3 C4 1.5391(15) . ?
C4 O2 1.2134(13) . ?
C4 C5 1.5143(15) . ?
C5 C6 1.5199(14) . ?
C6 C7 1.5160(14) . ?
C7 O3 1.2112(13) . ?
C7 C8 1.5420(14) . ?
C8 C17 1.5418(14) . ?
C8 C13 1.5426(14) . ?
C8 C9 1.5449(14) . ?
C9 O4 1.2107(13) . ?
C9 C10 1.5067(14) . ?
C10 C10 1.5179(19) 2_556 ?
C13 C14 1.5283(15) . ?
C14 C15 1.5279(17) . ?
C15 C16 1.5228(17) . ?
C16 C17 1.5323(15) . ?
 
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 C2 C1 121.56(10) . . ?
O1 C2 C3 120.89(10) . . ?
C1 C2 C3 117.55(10) . . ?
C11 C3 C12 110.12(9) . . ?
C11 C3 C4 111.86(9) . . ?
C12 C3 C4 110.58(9) . . ?
C11 C3 C2 109.90(9) . . ?
C12 C3 C2 110.12(9) . . ?
C4 C3 C2 104.12(8) . . ?
O2 C4 C5 121.19(10) . . ?
O2 C4 C3 120.94(10) . . ?
C5 C4 C3 117.79(9) . . ?
C4 C5 C6 111.76(9) . . ?
C7 C6 C5 110.95(9) . . ?
O3 C7 C6 121.09(9) . . ?
O3 C7 C8 120.85(9) . . ?
C6 C7 C8 118.05(9) . . ?
C17 C8 C7 110.69(8) . . ?
C17 C8 C13 110.23(8) . . ?
C7 C8 C13 109.98(8) . . ?
C17 C8 C9 110.42(8) . . ?
C7 C8 C9 103.99(8) . . ?
C13 C8 C9 111.37(8) . . ?
O4 C9 C10 121.76(9) . . ?
O4 C9 C8 121.04(9) . . ?
C10 C9 C8 117.18(8) . . ?
C9 C10 C10 112.09(11) . 2_556 ?
C14 C13 C8 111.53(9) . . ?
C15 C14 C13 111.18(9) . . ?
C16 C15 C14 111.35(9) . . ?
C15 C16 C17 111.98(9) . . ?
C16 C17 C8 111.79(9) . . ?
 
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
O1 C2 C3 C11 13.04(14) . . . . ?
C1 C2 C3 C11 -167.13(10) . . . . ?
O1 C2 C3 C12 134.52(11) . . . . ?
C1 C2 C3 C12 -45.65(13) . . . . ?
O1 C2 C3 C4 -106.92(11) . . . . ?
C1 C2 C3 C4 72.91(12) . . . . ?
C11 C3 C4 O2 147.14(10) . . . . ?
C12 C3 C4 O2 24.01(14) . . . . ?
C2 C3 C4 O2 -94.24(11) . . . . ?
C11 C3 C4 C5 -36.04(12) . . . . ?
C12 C3 C4 C5 -159.17(9) . . . . ?
C2 C3 C4 C5 82.58(11) . . . . ?
O2 C4 C5 C6 14.75(14) . . . . ?
C3 C4 C5 C6 -162.06(9) . . . . ?
C4 C5 C6 C7 64.65(11) . . . . ?
C5 C6 C7 O3 21.80(14) . . . . ?
C5 C6 C7 C8 -157.28(9) . . . . ?
O3 C7 C8 C17 136.32(10) . . . . ?
C6 C7 C8 C17 -44.60(12) . . . . ?
O3 C7 C8 C13 14.26(13) . . . . ?
C6 C7 C8 C13 -166.66(9) . . . . ?
O3 C7 C8 C9 -105.10(11) . . . . ?
C6 C7 C8 C9 73.98(11) . . . . ?
C17 C8 C9 O4 13.51(13) . . . . ?
C7 C8 C9 O4 -105.26(11) . . . . ?
C13 C8 C9 O4 136.33(10) . . . . ?
C17 C8 C9 C10 -167.74(9) . . . . ?
C7 C8 C9 C10 73.49(10) . . . . ?
C13 C8 C9 C10 -44.92(12) . . . . ?
O4 C9 C10 C10 14.53(16) . . . 2_556 ?
C8 C9 C10 C10 -164.20(10) . . . 2_556 ?
C17 C8 C13 C14 55.46(11) . . . . ?
C7 C8 C13 C14 177.78(8) . . . . ?
C9 C8 C13 C14 -67.47(11) . . . . ?
C8 C13 C14 C15 -56.51(12) . . . . ?
C13 C14 C15 C16 55.58(13) . . . . ?
C14 C15 C16 C17 -54.55(13) . . . . ?
C15 C16 C17 C8 54.28(12) . . . . ?
C7 C8 C17 C16 -176.04(9) . . . . ?
C13 C8 C17 C16 -54.13(11) . . . . ?
C9 C8 C17 C16 69.35(11) . . . . ?
 
_refine_diff_density_max    0.359
_refine_diff_density_min   -0.156
_refine_diff_density_rms    0.038























