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#$Date: 2025-08-18 17:20:24 +0300 (Mon, 18 Aug 2025) $
#$Revision: 301776 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/51/31/1513112.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_1513112
loop_
_publ_author_name
'Igarashi, Yasuhiro'
'Zhou, Tao'
'Sato, Seizo'
'Matsumoto, Takashi'
'Yu, Linkai'
'Oku, Naoya'
_publ_section_title
;
 Akaeolide, a carbocyclic polyketide from marine-derived streptomyces.
;
_journal_issue                   22
_journal_name_full               'Organic letters'
_journal_page_first              5678
_journal_page_last               5681
_journal_paper_doi               10.1021/ol402661r
_journal_volume                  15
_journal_year                    2013
_chemical_absolute_configuration 'CHOOSE rm ad rmad syn or unk'
_chemical_formula_moiety         'C22 H31 Cl O6'
_chemical_formula_sum            'C22 H31 Cl O6'
_chemical_formula_weight         426.94
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_Int_Tables_number      19
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90.0000
_cell_angle_beta                 90.0000
_cell_angle_gamma                90.0000
_cell_formula_units_Z            4
_cell_length_a                   9.5078(2)
_cell_length_b                   10.0045(3)
_cell_length_c                   22.4594(6)
_cell_measurement_reflns_used    22187
_cell_measurement_temperature    93
_cell_measurement_theta_max      68.16
_cell_measurement_theta_min      3.94
_cell_volume                     2136.36(10)
_computing_cell_refinement       'RAPID AUTO'
_computing_data_collection       'RAPID AUTO (Rigaku, ????)'
_computing_data_reduction        'RAPID AUTO'
_computing_molecular_graphics    'CrystalStructure 4.1'
_computing_publication_material  'CrystalStructure 4.1 (Rigaku, 2013)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'Il Milione (Burla, et al., 2007)'
_diffrn_ambient_temperature      93
_diffrn_detector_area_resol_mean 10.000
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Rigaku R-AXIS RAPID II'
_diffrn_measurement_method       ω
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54187
_diffrn_reflns_av_R_equivalents  0.0444
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            25505
_diffrn_reflns_theta_full        68.16
_diffrn_reflns_theta_max         68.16
_diffrn_reflns_theta_min         3.94
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.886
_exptl_absorpt_correction_T_max  0.901
_exptl_absorpt_correction_T_min  0.726
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'ABSCOR (Rigaku, 1995)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.327
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       platelet
_exptl_crystal_F_000             912.00
_exptl_crystal_size_max          0.154
_exptl_crystal_size_mid          0.122
_exptl_crystal_size_min          0.055
_refine_diff_density_max         0.27
_refine_diff_density_min         -0.19
_refine_ls_abs_structure_details
'Flack, H. D. (1983), Acta Cryst. A39, 876-881.  1658 Friedel Pairs'
_refine_ls_abs_structure_Flack   0.026(14)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.067
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_parameters     267
_refine_ls_number_reflns         3902
_refine_ls_number_restraints     0
_refine_ls_R_factor_gt           0.0364
_refine_ls_shift/su_max          0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[σ²(Fo²)+(0.0532P)²+0.4417P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.0918
_reflns_number_gt                3781
_reflns_number_total             3902
_reflns_threshold_expression     F²>2.0σ(F²)
_cod_data_source_file            ol402661r_si_001.cif
_cod_data_source_block           SX190-VariMax-RAPID
_cod_original_cell_volume        2136.34(9)
_cod_database_code               1513112
loop_
_symmetry_equiv_pos_site_id
_symmetry_equiv_pos_as_xyz
1 +X,+Y,+Z
2 1/2+X,1/2-Y,-Z
3 -X,1/2+Y,1/2-Z
4 1/2-X,-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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
Cl1 Cl 1.11830(5) 0.22661(6) 0.62827(3) 0.04728(17) Uani 1 4 d .
O2 O 0.37963(14) 0.52082(13) 0.63645(5) 0.0275(3) Uani 1 4 d .
O3 O 0.79424(14) 0.14493(12) 0.61617(5) 0.0259(3) Uani 1 4 d .
O4 O 0.68194(13) 0.46238(12) 0.61617(5) 0.0242(3) Uani 1 4 d .
O5 O 0.84531(15) 0.25151(13) 0.53355(6) 0.0333(3) Uani 1 4 d .
O6 O 0.49949(15) 0.11077(14) 0.75464(6) 0.0308(3) Uani 1 4 d .
O7 O 0.98042(17) 0.43533(16) 0.71675(7) 0.0437(4) Uani 1 4 d .
C1 C 0.8097(3) 0.3310(3) 0.88402(9) 0.0426(5) Uani 1 4 d .
C2 C 0.7650(2) 0.3427(2) 0.81911(9) 0.0345(5) Uani 1 4 d .
C3 C 0.8389(2) 0.23707(19) 0.78120(8) 0.0261(4) Uani 1 4 d .
C4 C 0.81494(19) 0.25537(18) 0.71390(7) 0.0232(4) Uani 1 4 d .
C5 C 0.8135(2) 0.12265(18) 0.68008(8) 0.0246(4) Uani 1 4 d .
C6 C 0.6927(2) 0.02856(18) 0.69757(8) 0.0247(4) Uani 1 4 d .
C7 C 0.55304(19) 0.10063(18) 0.70579(7) 0.0235(4) Uani 1 4 d .
C8 C 0.49153(19) 0.16945(18) 0.65253(8) 0.0233(4) Uani 1 4 d .
C9 C 0.46591(17) 0.29948(19) 0.65979(7) 0.0224(4) Uani 1 4 d .
C10 C 0.43608(19) 0.40145(18) 0.61172(7) 0.0225(4) Uani 1 4 d .
C11 C 0.5704(2) 0.42460(17) 0.57558(7) 0.0220(4) Uani 1 4 d .
C12 C 0.5631(2) 0.53392(18) 0.52692(7) 0.0262(4) Uani 1 4 d .
C13 C 0.6420(2) 0.65009(19) 0.55579(8) 0.0292(4) Uani 1 4 d .
C14 C 0.7518(2) 0.58388(19) 0.59569(8) 0.0264(4) Uani 1 4 d .
C15 C 0.8831(2) 0.54394(19) 0.55918(9) 0.0306(4) Uani 1 4 d .
C16 C 1.0010(2) 0.4623(2) 0.58938(9) 0.0338(5) Uani 1 4 d .
C17 C 0.96004(19) 0.33210(19) 0.62153(9) 0.0306(4) Uani 1 4 d .
C18 C 0.8616(2) 0.24281(18) 0.58640(8) 0.0270(4) Uani 1 4 d .
C19 C 0.9224(2) 0.3500(2) 0.68771(9) 0.0295(4) Uani 1 4 d .
C20 C 0.4793(2) 0.09379(19) 0.59481(8) 0.0293(4) Uani 1 4 d .
C21 C 0.4174(2) 0.56969(19) 0.50375(8) 0.0308(4) Uani 1 4 d .
C22 C 0.7877(2) 0.6676(2) 0.64965(9) 0.0315(4) Uani 1 4 d .
H1A H 0.75459 0.39334 0.90826 0.0511 Uiso 1 4 calc R
H1B H 0.90988 0.35254 0.88763 0.0511 Uiso 1 4 calc R
H1C H 0.79339 0.23942 0.89794 0.0511 Uiso 1 4 calc R
H2A H 0.78883 0.43291 0.80402 0.0414 Uiso 1 4 calc R
H2B H 0.66188 0.331 0.81602 0.0414 Uiso 1 4 calc R
H2 H 0.43282 0.54844 0.66366 0.0330 Uiso 1 4 calc R
H3A H 0.80466 0.14754 0.79311 0.0313 Uiso 1 4 calc R
H3B H 0.94118 0.24051 0.7894 0.0313 Uiso 1 4 calc R
H4 H 0.72032 0.29741 0.70866 0.0278 Uiso 1 4 calc R
H5 H 0.9051 0.07578 0.68668 0.0295 Uiso 1 4 calc R
H6A H 0.68178 -0.04047 0.66632 0.0297 Uiso 1 4 calc R
H6B H 0.71753 -0.01746 0.73515 0.0297 Uiso 1 4 calc R
H9 H 0.46645 0.33164 0.69959 0.0268 Uiso 1 4 calc R
H10 H 0.3638 0.36271 0.58436 0.0270 Uiso 1 4 calc R
H11 H 0.59719 0.33834 0.55615 0.0264 Uiso 1 4 calc R
H12 H 0.62028 0.50247 0.49227 0.0315 Uiso 1 4 calc R
H13A H 0.6877 0.70657 0.5252 0.0350 Uiso 1 4 calc R
H13B H 0.57722 0.70625 0.57956 0.0350 Uiso 1 4 calc R
H15A H 0.85021 0.49223 0.52427 0.0367 Uiso 1 4 calc R
H15B H 0.92589 0.62721 0.54374 0.0367 Uiso 1 4 calc R
H16A H 1.07154 0.4396 0.55855 0.0406 Uiso 1 4 calc R
H16B H 1.04812 0.5211 0.61868 0.0406 Uiso 1 4 calc R
H20A H 0.57083 0.09237 0.57479 0.0352 Uiso 1 4 calc R
H20B H 0.41 0.13779 0.56911 0.0352 Uiso 1 4 calc R
H20C H 0.44894 0.00197 0.60295 0.0352 Uiso 1 4 calc R
H21A H 0.36989 0.48854 0.48983 0.0370 Uiso 1 4 calc R
H21B H 0.42614 0.63305 0.47068 0.0370 Uiso 1 4 calc R
H21C H 0.36222 0.61049 0.53583 0.0370 Uiso 1 4 calc R
H22A H 0.82925 0.75243 0.63672 0.0378 Uiso 1 4 calc R
H22B H 0.85507 0.61926 0.67466 0.0378 Uiso 1 4 calc R
H22C H 0.70192 0.68546 0.67253 0.0378 Uiso 1 4 calc R
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091
;
International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.0000 0.0000
;
International Tables for Crystallography
(1992, Vol. C, Table 6.1.1.4)
;
Cl Cl 0.3639 0.7018
;
International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
O O 0.0492 0.0322
;
International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_publ_flag
C5 O3 C18 122.51(14) yes
C11 O4 C14 110.61(12) yes
C1 C2 C3 110.57(17) yes
C2 C3 C4 113.36(16) yes
C3 C4 C5 112.68(15) yes
C3 C4 C19 110.87(15) yes
C5 C4 C19 110.88(15) yes
O3 C5 C4 110.84(14) yes
O3 C5 C6 104.50(14) yes
C4 C5 C6 114.30(15) yes
C5 C6 C7 113.14(15) yes
O6 C7 C6 121.01(16) yes
O6 C7 C8 121.28(17) yes
C6 C7 C8 117.46(14) yes
C7 C8 C9 114.95(16) yes
C7 C8 C20 119.10(15) yes
C9 C8 C20 125.56(16) yes
C8 C9 C10 127.23(15) yes
O2 C10 C9 111.00(13) yes
O2 C10 C11 113.26(14) yes
C9 C10 C11 108.91(14) yes
O4 C11 C10 108.45(13) yes
O4 C11 C12 107.03(14) yes
C10 C11 C12 116.35(15) yes
C11 C12 C13 102.47(14) yes
C11 C12 C21 116.63(16) yes
C13 C12 C21 114.40(16) yes
C12 C13 C14 104.76(15) yes
O4 C14 C13 103.62(14) yes
O4 C14 C15 108.61(15) yes
O4 C14 C22 108.15(14) yes
C13 C14 C15 110.65(15) yes
C13 C14 C22 112.60(16) yes
C15 C14 C22 112.71(16) yes
C14 C15 C16 119.35(16) yes
C15 C16 C17 118.02(17) yes
Cl1 C17 C16 108.43(13) yes
Cl1 C17 C18 102.07(13) yes
Cl1 C17 C19 100.20(13) yes
C16 C17 C18 114.26(16) yes
C16 C17 C19 114.41(16) yes
C18 C17 C19 115.35(15) yes
O3 C18 O5 118.80(16) yes
O3 C18 C17 117.62(15) yes
O5 C18 C17 123.51(17) yes
O7 C19 C4 122.76(18) yes
O7 C19 C17 119.86(18) yes
C4 C19 C17 117.36(16) yes
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
Cl1 C17 1.8441(19) yes
O2 C10 1.422(2) yes
O3 C5 1.464(2) yes
O3 C18 1.348(2) yes
O4 C11 1.449(2) yes
O4 C14 1.459(2) yes
O5 C18 1.200(2) yes
O6 C7 1.214(2) yes
O7 C19 1.207(3) yes
C1 C2 1.523(3) yes
C2 C3 1.529(3) yes
C3 C4 1.540(2) yes
C4 C5 1.530(3) yes
C4 C19 1.512(3) yes
C5 C6 1.536(3) yes
C6 C7 1.522(3) yes
C7 C8 1.499(2) yes
C8 C9 1.333(3) yes
C8 C20 1.506(3) yes
C9 C10 1.512(2) yes
C10 C11 1.531(3) yes
C11 C12 1.548(2) yes
C12 C13 1.528(3) yes
C12 C21 1.523(3) yes
C13 C14 1.527(3) yes
C14 C15 1.546(3) yes
C14 C22 1.512(3) yes
C15 C16 1.545(3) yes
C16 C17 1.539(3) yes
C17 C18 1.515(3) yes
C17 C19 1.539(3) yes
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139041660
