#------------------------------------------------------------------------------
#$Date: 2020-06-05 14:27:41 +0300 (Fri, 05 Jun 2020) $
#$Revision: 252907 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/15/74/7157457.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_7157457
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 H30 O4'
_chemical_formula_sum            'C20 H30 O4'
_chemical_formula_weight         334.44
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2018/3
_cell_angle_alpha                90
_cell_angle_beta                 98.444(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.8166(4)
_cell_length_b                   12.8538(5)
_cell_length_c                   14.9915(7)
_cell_measurement_reflns_used    10446
_cell_measurement_temperature    123(2)
_cell_measurement_theta_max      29.3310
_cell_measurement_theta_min      2.6020
_cell_volume                     1871.13(14)
_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 1.000
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC11 (RCD3): quarter-chi single'
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0330
_diffrn_reflns_av_unetI/netI     0.0222
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            23195
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.995
_diffrn_reflns_theta_min         2.332
_diffrn_source                   'Rotating-anode X-ray tube (dual wavelength)'
_diffrn_source_type              'Rigaku (Mo) X-ray DW Source'
_exptl_absorpt_coefficient_mu    0.081
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.64662
_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    1.187
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             728
_exptl_crystal_size_max          0.600
_exptl_crystal_size_mid          0.450
_exptl_crystal_size_min          0.320
_refine_diff_density_max         0.539
_refine_diff_density_min         -0.318
_refine_diff_density_rms         0.051
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     219
_refine_ls_number_reflns         4072
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.058
_refine_ls_R_factor_all          0.0619
_refine_ls_R_factor_gt           0.0562
_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)+(0.0724P)²+1.2193P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1483
_refine_ls_wR_factor_ref         0.1528
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3605
_reflns_number_total             4072
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d0ob00501k3.cif
_cod_data_source_block           Compound3b
_cod_depositor_comments
'Adding full bibliography for 7157456--7157460.cif.'
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               7157457
_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   0.953
_shelx_estimated_absorpt_t_max   0.975
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.8836(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 . . . . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_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_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_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) . . . . ?
