#------------------------------------------------------------------------------
#$Date: 2020-06-05 14:27:41 +0300 (Fri, 05 Jun 2020) $
#$Revision: 252907 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/15/74/7157456.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_7157456
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         'C22 H28 O2 Si'
_chemical_formula_sum            'C22 H28 O2 Si'
_chemical_formula_weight         352.53
_space_group_crystal_system      monoclinic
_space_group_IT_number           5
_space_group_name_Hall           'C 2y'
_space_group_name_H-M_alt        'C 1 2 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2018/3
_cell_angle_alpha                90
_cell_angle_beta                 104.859(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   19.7751(7)
_cell_length_b                   7.6977(3)
_cell_length_c                   13.7091(5)
_cell_measurement_reflns_used    10487
_cell_measurement_temperature    123(2)
_cell_measurement_theta_max      29.3990
_cell_measurement_theta_min      2.9110
_cell_volume                     2017.05(13)
_computing_cell_refinement       'CrysAlisPro 1.171.39.43a (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.43a (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.43a (Rigaku OD, 2018)'
_computing_molecular_graphics
'Yadokari-XG 2009 (Wakita Nemoto et al., 2009)'
_computing_publication_material
'Yadokari-XG 2009 (Wakita Nemoto et al., 2009)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      123(2)
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC11 (RCD3): quarter-chi single'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0261
_diffrn_reflns_av_unetI/netI     0.0238
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            11900
_diffrn_reflns_point_group_measured_fraction_full 0.933
_diffrn_reflns_point_group_measured_fraction_max 0.933
_diffrn_reflns_theta_full        24.998
_diffrn_reflns_theta_max         24.998
_diffrn_reflns_theta_min         2.286
_diffrn_source                   'Rotating-anode X-ray tube (dual wavelength)'
_diffrn_source_type              'Rigaku (Mo) X-ray DW Source'
_exptl_absorpt_coefficient_mu    0.128
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.64328
_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_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.161
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             760
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.060
_refine_diff_density_max         0.146
_refine_diff_density_min         -0.191
_refine_diff_density_rms         0.035
_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)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.082
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     230
_refine_ls_number_reflns         3316
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.081
_refine_ls_R_factor_all          0.0275
_refine_ls_R_factor_gt           0.0268
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0368P)²+0.8980P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0715
_refine_ls_wR_factor_ref         0.0720
_reflns_Friedel_coverage         0.727
_reflns_Friedel_fraction_full    0.856
_reflns_Friedel_fraction_max     0.856
_reflns_number_gt                3240
_reflns_number_total             3316
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d0ob00501k3.cif
_cod_data_source_block           Compound2d
_cod_depositor_comments
'Adding full bibliography for 7157456--7157460.cif.'
_cod_original_sg_symbol_H-M      'C 2'
_cod_database_code               7157456
_shelx_shelxl_version_number     2018/3
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_min   0.951
_shelx_estimated_absorpt_t_max   0.992
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'
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 . . .
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
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_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_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) . . . . ?
