#------------------------------------------------------------------------------
#$Date: 2020-06-05 13:27:41 +0200 (Fri 05 de Jun de 2020) $
#$Revision: 252907 $
#$URL: svn://www.crystallography.net/cod/cif/7/15/74/7157458.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_7157458
loop_
_publ_author_name
'Sarkar, Parantap'
'Inaba, Yuya'
'Shirakura, Hayato'
'Yoneda, Tomoki'
'Inokuma, Yasuhide'
_publ_section_title
;
 Modular synthesis of oligoacetylacetones via site-selective silylation of
 acetylacetone derivatives.
;
_journal_issue                   17
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              3297
_journal_page_last               3302
_journal_paper_doi               10.1039/d0ob00501k
_journal_volume                  18
_journal_year                    2020
_chemical_formula_moiety         'C20 H38 O4 Si2'
_chemical_formula_sum            'C10 H19 O2 Si'
_chemical_formula_weight         199.34
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2017/1
_cell_angle_alpha                90
_cell_angle_beta                 90.224(6)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.1033(14)
_cell_length_b                   15.700(3)
_cell_length_c                   10.748(2)
_cell_measurement_reflns_used    7967
_cell_measurement_temperature    123(2)
_cell_measurement_theta_max      27.51
_cell_measurement_theta_min      1.89
_cell_volume                     1198.6(4)
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_diffrn_ambient_temperature      123(2)
_diffrn_detector                 'Image Plate'
_diffrn_detector_area_resol_mean 10
_diffrn_detector_type            'Rigaku IP'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.998
_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_reflns_av_R_equivalents  0.0703
_diffrn_reflns_av_unetI/netI     0.0663
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            10679
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.483
_diffrn_reflns_theta_min         1.895
_diffrn_source                   'sealed X-ray tube'
_exptl_absorpt_coefficient_mu    0.167
_exptl_absorpt_correction_T_max  0.9936
_exptl_absorpt_correction_T_min  0.1822
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'ABSCOR(Rigaku, 1995)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.105
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             436
_exptl_crystal_size_max          0.320
_exptl_crystal_size_mid          0.260
_exptl_crystal_size_min          0.090
_refine_diff_density_max         0.482
_refine_diff_density_min         -0.471
_refine_diff_density_rms         0.062
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.075
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     124
_refine_ls_number_reflns         2726
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.075
_refine_ls_R_factor_all          0.0970
_refine_ls_R_factor_gt           0.0694
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0924P)²+0.7584P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1738
_refine_ls_wR_factor_ref         0.1941
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2002
_reflns_number_total             2726
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d0ob00501k3.cif
_cod_data_source_block           Compound5a
_cod_depositor_comments
'Adding full bibliography for 7157456--7157460.cif.'
_cod_original_cell_volume        1198.7(4)
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               7157458
_shelx_shelxl_version_number     2017/1
_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.
;
_shelx_estimated_absorpt_t_min   0.948
_shelx_estimated_absorpt_t_max   0.985
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
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 . . .
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'
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_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_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 ?
