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#$Date: 2022-10-22 00:46:04 +0300 (Sat, 22 Oct 2022) $
#$Revision: 278716 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/56/78/1567830.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_1567830
loop_
_publ_author_name
'Sharma, Himangshu'
'Mondal, Joyanta Mr.'
'Ghosh, Ananyo K. Mr.'
'Pal, Ritesh Ranjan Dr.'
'Goswami, Rajib Kumar'
_publ_section_title
;
 Total Synthesis of Antibacterial Polyketide Natural Product Thailandamide
 Lactone
;
_journal_name_full               'Chemical Science'
_journal_paper_doi               10.1039/D2SC04727F
_journal_year                    2022
_chemical_absolute_configuration rmad
_chemical_formula_moiety         'C28 H29 O4'
_chemical_formula_sum            'C28 H30 O4'
_chemical_formula_weight         430.52
_space_group_crystal_system      tetragonal
_space_group_IT_number           92
_space_group_name_Hall           'P 4abw 2nw'
_space_group_name_H-M_alt        'P 41 21 2'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2022-05-27
_audit_creation_method
;
Olex2 1.3-ac4
(compiled 2019.04.23 svn.r3594 for Rigaku Oxford Diffraction, GUI svn.r5739)
;
_audit_update_record
;
2022-07-05 deposited with the CCDC.	2022-10-21 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   9.6794(11)
_cell_length_b                   9.6794(11)
_cell_length_c                   49.548(8)
_cell_measurement_reflns_used    6410
_cell_measurement_temperature    105.33
_cell_measurement_theta_max      24.25
_cell_measurement_theta_min      2.26
_cell_volume                     4642.2(11)
_computing_cell_refinement       'SAINT V8.38A (?, 2016)'
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      105.33
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker APEX-III PHOTON II'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1132
_diffrn_reflns_av_unetI/netI     0.0519
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       59
_diffrn_reflns_limit_l_min       -59
_diffrn_reflns_number            44343
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.086
_diffrn_reflns_theta_max         25.086
_diffrn_reflns_theta_min         2.259
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.081
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_correction_T_min  0.5859
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1289 before and 0.0798 after correction. The Ratio of minimum to maximum transmission is 0.7862. The λ/2 correction factor is Not present.'
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.232
_exptl_crystal_description       plate
_exptl_crystal_F_000             1840
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.09
_refine_diff_density_max         0.345
_refine_diff_density_min         -0.260
_refine_diff_density_rms         0.054
_refine_ls_abs_structure_details
;
 Flack x determined using 1167 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.5(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.155
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     292
_refine_ls_number_reflns         4139
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.155
_refine_ls_R_factor_all          0.0731
_refine_ls_R_factor_gt           0.0512
_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)+(0.0382P)²+3.2109P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1149
_refine_ls_wR_factor_ref         0.1280
_reflns_Friedel_coverage         0.637
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.999
_reflns_number_gt                3406
_reflns_number_total             4139
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d2sc04727f2.cif
_cod_data_source_block           mo_ocrg170321_0m_a
_cod_original_cell_volume        4642.2(13)
_cod_database_code               1567830
_shelx_shelxl_version_number     2016/6
_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_max   0.993
_shelx_estimated_absorpt_t_min   0.975
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C4(H4), C2(H2)
2.b Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B)
2.c Aromatic/amide H refined with riding coordinates:
 C24(H24), C8(H8), C16(H16), C22(H22), C28(H28), C13(H13), C12(H12), C26(H26),
 C14(H14), C25(H25), C27(H27), C15(H15), C21(H21), C20(H20), C18(H18), C19(H19)
2.d Idealised Me refined as rotating group:
 C7(H7A,H7B,H7C), C3(H3A,H3B,H3C), C5(H5A,H5B,H5C)
;
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-y+1/2, x+1/2, z+1/4'
'-x, -y, z+1/2'
'y+1/2, -x+1/2, z+3/4'
'x+1/2, -y+1/2, -z+3/4'
'-x+1/2, y+1/2, -z+1/4'
'y, x, -z'
'-y, -x, -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
O1 O -0.5594(3) -0.1672(3) -0.33656(5) 0.0215(6) Uani 1 1 d . . . . .
O2 O -0.2923(3) -0.0060(3) -0.42767(5) 0.0270(6) Uani 1 1 d . . . . .
O3 O -0.2941(3) -0.2702(3) -0.47314(5) 0.0315(7) Uani 1 1 d . . . . .
O4 O -0.0993(3) -0.1488(3) -0.47480(5) 0.0391(8) Uani 1 1 d . . . . .
C1 C -0.1922(4) -0.2120(4) -0.46169(7) 0.0221(9) Uani 1 1 d . . . . .
C17 C -0.7536(4) -0.1654(4) -0.30694(7) 0.0202(8) Uani 1 1 d . . . . .
C11 C -0.6478(4) -0.3871(4) -0.32052(7) 0.0205(8) Uani 1 1 d . . . . .
C23 C -0.5156(4) -0.2131(4) -0.28935(7) 0.0207(8) Uani 1 1 d . . . . .
C6 C -0.2969(4) -0.1516(4) -0.38742(7) 0.0204(8) Uani 1 1 d . . . . .
C24 C -0.4063(4) -0.3026(4) -0.28412(8) 0.0256(9) Uani 1 1 d . . . . .
H24 H -0.398569 -0.386400 -0.293980 0.031 Uiso 1 1 calc R . . . .
C8 C -0.4095(4) -0.1961(4) -0.37433(7) 0.0217(9) Uani 1 1 d . . . . .
H8 H -0.488014 -0.216634 -0.385109 0.026 Uiso 1 1 calc R . . . .
C4 C -0.3005(4) -0.1461(4) -0.41811(7) 0.0204(8) Uani 1 1 d . . . . .
H4 H -0.388405 -0.188748 -0.424660 0.024 Uiso 1 1 calc R . . . .
C9 C -0.4250(4) -0.2170(4) -0.34455(7) 0.0218(9) Uani 1 1 d . . . . .
H9A H -0.416047 -0.316250 -0.340086 0.026 Uiso 1 1 calc R . . . .
H9B H -0.352021 -0.165647 -0.334782 0.026 Uiso 1 1 calc R . . . .
C2 C -0.1780(4) -0.2198(4) -0.43126(7) 0.0213(8) Uani 1 1 d . . . . .
H2 H -0.091175 -0.170992 -0.425880 0.026 Uiso 1 1 calc R . . . .
C16 C -0.6908(4) -0.4157(4) -0.34686(7) 0.0262(9) Uani 1 1 d . . . . .
H16 H -0.694645 -0.342736 -0.359664 0.031 Uiso 1 1 calc R . . . .
C22 C -0.8381(4) -0.2217(4) -0.28674(8) 0.0253(9) Uani 1 1 d . . . . .
H22 H -0.810815 -0.304468 -0.277916 0.030 Uiso 1 1 calc R . . . .
C28 C -0.5244(4) -0.0913(4) -0.27442(8) 0.0270(9) Uani 1 1 d . . . . .
H28 H -0.598842 -0.029373 -0.277529 0.032 Uiso 1 1 calc R . . . .
C13 C -0.6842(4) -0.6288(4) -0.30986(8) 0.0273(10) Uani 1 1 d . . . . .
H13 H -0.681830 -0.701965 -0.297101 0.033 Uiso 1 1 calc R . . . .
C12 C -0.6480(4) -0.4958(4) -0.30202(8) 0.0233(9) Uani 1 1 d . . . . .
H12 H -0.622960 -0.478612 -0.283791 0.028 Uiso 1 1 calc R . . . .
C10 C -0.6156(4) -0.2360(4) -0.31301(7) 0.0208(9) Uani 1 1 d . . . . .
C26 C -0.3169(4) -0.1482(4) -0.25006(8) 0.0297(10) Uani 1 1 d . . . . .
H26 H -0.249064 -0.125880 -0.236907 0.036 Uiso 1 1 calc R . . . .
C7 C -0.1644(4) -0.1050(5) -0.37447(7) 0.0279(10) Uani 1 1 d . . . . .
H7A H -0.175959 -0.102653 -0.354823 0.042 Uiso 1 1 calc GR . . . .
H7B H -0.140679 -0.012368 -0.380988 0.042 Uiso 1 1 calc GR . . . .
H7C H -0.090150 -0.169509 -0.379146 0.042 Uiso 1 1 calc GR . . . .
C14 C -0.7237(4) -0.6548(5) -0.33620(8) 0.0302(10) Uani 1 1 d . . . . .
H14 H -0.747913 -0.745821 -0.341575 0.036 Uiso 1 1 calc R . . . .
C3 C -0.1667(5) -0.3711(4) -0.42262(8) 0.0283(10) Uani 1 1 d . . . . .
H3A H -0.252216 -0.419727 -0.427297 0.042 Uiso 1 1 calc GR . . . .
H3B H -0.151923 -0.376040 -0.403079 0.042 Uiso 1 1 calc GR . . . .
H3C H -0.088699 -0.414502 -0.431962 0.042 Uiso 1 1 calc GR . . . .
C25 C -0.3081(5) -0.2703(5) -0.26454(8) 0.0308(10) Uani 1 1 d . . . . .
H25 H -0.234339 -0.332656 -0.261095 0.037 Uiso 1 1 calc R . . . .
C27 C -0.4255(4) -0.0594(5) -0.25500(8) 0.0306(10) Uani 1 1 d . . . . .
H27 H -0.432786 0.024185 -0.245067 0.037 Uiso 1 1 calc R . . . .
C15 C -0.7278(4) -0.5477(5) -0.35472(8) 0.0319(10) Uani 1 1 d . . . . .
H15 H -0.755955 -0.564903 -0.372773 0.038 Uiso 1 1 calc R . . . .
C21 C -0.9604(4) -0.1584(4) -0.27950(8) 0.0299(10) Uani 1 1 d . . . . .
H21 H -1.016491 -0.197461 -0.265732 0.036 Uiso 1 1 calc R . . . .
C20 C -1.0014(4) -0.0382(5) -0.29225(8) 0.0315(10) Uani 1 1 d . . . . .
H20 H -1.085770 0.005278 -0.287362 0.038 Uiso 1 1 calc R . . . .
C18 C -0.7946(4) -0.0447(4) -0.31935(8) 0.0296(10) Uani 1 1 d . . . . .
H18 H -0.737938 -0.004078 -0.332844 0.036 Uiso 1 1 calc R . . . .
C19 C -0.9192(5) 0.0180(5) -0.31211(9) 0.0380(11) Uani 1 1 d . . . . .
H19 H -0.947461 0.100328 -0.320976 0.046 Uiso 1 1 calc R . . . .
C5 C -0.4162(5) 0.0721(5) -0.42287(9) 0.0370(12) Uani 1 1 d . . . . .
H5A H -0.494338 0.026776 -0.431794 0.056 Uiso 1 1 calc GR . . . .
H5B H -0.405037 0.165654 -0.430118 0.056 Uiso 1 1 calc GR . . . .
H5C H -0.433677 0.077211 -0.403409 0.056 Uiso 1 1 calc GR . . . .
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
C9 O1 C10 113.9(3) . . ?
C5 O2 C4 113.3(3) . . ?
O3 C1 C2 119.5(3) . . ?
O4 C1 O3 122.4(3) . . ?
O4 C1 C2 118.0(3) . . ?
C22 C17 C10 118.4(3) . . ?
C18 C17 C22 118.6(4) . . ?
C18 C17 C10 122.8(3) . . ?
C16 C11 C10 118.3(3) . . ?
C12 C11 C16 117.6(4) . . ?
C12 C11 C10 123.9(3) . . ?
C24 C23 C28 118.3(4) . . ?
C24 C23 C10 122.1(3) . . ?
C28 C23 C10 119.3(4) . . ?
C8 C6 C4 118.5(3) . . ?
C8 C6 C7 125.7(3) . . ?
C7 C6 C4 115.8(3) . . ?
C23 C24 H24 119.7 . . ?
C23 C24 C25 120.6(4) . . ?
C25 C24 H24 119.7 . . ?
C6 C8 H8 116.5 . . ?
C6 C8 C9 127.1(4) . . ?
C9 C8 H8 116.5 . . ?
O2 C4 C6 111.1(3) . . ?
O2 C4 H4 109.2 . . ?
O2 C4 C2 104.9(3) . . ?
C6 C4 H4 109.2 . . ?
C6 C4 C2 113.1(3) . . ?
C2 C4 H4 109.2 . . ?
O1 C9 C8 108.4(3) . . ?
O1 C9 H9A 110.0 . . ?
O1 C9 H9B 110.0 . . ?
C8 C9 H9A 110.0 . . ?
C8 C9 H9B 110.0 . . ?
H9A C9 H9B 108.4 . . ?
C1 C2 C4 109.3(3) . . ?
C1 C2 H2 108.5 . . ?
C1 C2 C3 109.4(3) . . ?
C4 C2 H2 108.5 . . ?
C4 C2 C3 112.5(3) . . ?
C3 C2 H2 108.5 . . ?
C11 C16 H16 119.2 . . ?
C15 C16 C11 121.5(4) . . ?
C15 C16 H16 119.2 . . ?
C17 C22 H22 119.6 . . ?
C21 C22 C17 120.9(4) . . ?
C21 C22 H22 119.6 . . ?
C23 C28 H28 119.6 . . ?
C27 C28 C23 120.8(4) . . ?
C27 C28 H28 119.6 . . ?
C12 C13 H13 119.9 . . ?
C14 C13 H13 119.9 . . ?
C14 C13 C12 120.1(4) . . ?
C11 C12 H12 119.5 . . ?
C13 C12 C11 121.0(4) . . ?
C13 C12 H12 119.5 . . ?
O1 C10 C17 106.3(3) . . ?
O1 C10 C11 108.5(3) . . ?
O1 C10 C23 108.2(3) . . ?
C17 C10 C11 107.1(3) . . ?
C17 C10 C23 109.6(3) . . ?
C23 C10 C11 116.7(3) . . ?
C25 C26 H26 120.4 . . ?
C27 C26 H26 120.4 . . ?
C27 C26 C25 119.1(4) . . ?
C6 C7 H7A 109.5 . . ?
C6 C7 H7B 109.5 . . ?
C6 C7 H7C 109.5 . . ?
H7A C7 H7B 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C13 C14 H14 120.1 . . ?
C13 C14 C15 119.8(4) . . ?
C15 C14 H14 120.1 . . ?
C2 C3 H3A 109.5 . . ?
C2 C3 H3B 109.5 . . ?
C2 C3 H3C 109.5 . . ?
H3A C3 H3B 109.5 . . ?
H3A C3 H3C 109.5 . . ?
H3B C3 H3C 109.5 . . ?
C24 C25 H25 119.7 . . ?
C26 C25 C24 120.6(4) . . ?
C26 C25 H25 119.7 . . ?
C28 C27 H27 119.7 . . ?
C26 C27 C28 120.6(4) . . ?
C26 C27 H27 119.7 . . ?
C16 C15 C14 119.8(4) . . ?
C16 C15 H15 120.1 . . ?
C14 C15 H15 120.1 . . ?
C22 C21 H21 120.0 . . ?
C22 C21 C20 120.1(4) . . ?
C20 C21 H21 120.0 . . ?
C21 C20 H20 120.2 . . ?
C19 C20 C21 119.6(4) . . ?
C19 C20 H20 120.2 . . ?
C17 C18 H18 119.9 . . ?
C17 C18 C19 120.2(4) . . ?
C19 C18 H18 119.9 . . ?
C20 C19 C18 120.7(4) . . ?
C20 C19 H19 119.7 . . ?
C18 C19 H19 119.7 . . ?
O2 C5 H5A 109.5 . . ?
O2 C5 H5B 109.5 . . ?
O2 C5 H5C 109.5 . . ?
H5A C5 H5B 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 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
O1 C9 1.442(4) . ?
O1 C10 1.450(4) . ?
O2 C4 1.438(5) . ?
O2 C5 1.438(5) . ?
O3 C1 1.269(5) . ?
O4 C1 1.267(5) . ?
C1 C2 1.516(5) . ?
C17 C22 1.403(5) . ?
C17 C10 1.530(5) . ?
C17 C18 1.379(5) . ?
C11 C16 1.398(5) . ?
C11 C12 1.395(5) . ?
C11 C10 1.541(5) . ?
C23 C24 1.392(6) . ?
C23 C28 1.394(6) . ?
C23 C10 1.536(5) . ?
C6 C8 1.339(5) . ?
C6 C4 1.522(5) . ?
C6 C7 1.504(5) . ?
C24 H24 0.9500 . ?
C24 C25 1.394(6) . ?
C8 H8 0.9500 . ?
C8 C9 1.497(5) . ?
C4 H4 1.0000 . ?
C4 C2 1.529(5) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C2 H2 1.0000 . ?
C2 C3 1.530(5) . ?
C16 H16 0.9500 . ?
C16 C15 1.383(6) . ?
C22 H22 0.9500 . ?
C22 C21 1.381(6) . ?
C28 H28 0.9500 . ?
C28 C27 1.392(6) . ?
C13 H13 0.9500 . ?
C13 C12 1.389(6) . ?
C13 C14 1.383(6) . ?
C12 H12 0.9500 . ?
C26 H26 0.9500 . ?
C26 C25 1.385(6) . ?
C26 C27 1.379(6) . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C14 H14 0.9500 . ?
C14 C15 1.384(6) . ?
C3 H3A 0.9800 . ?
C3 H3B 0.9800 . ?
C3 H3C 0.9800 . ?
C25 H25 0.9500 . ?
C27 H27 0.9500 . ?
C15 H15 0.9500 . ?
C21 H21 0.9500 . ?
C21 C20 1.382(6) . ?
C20 H20 0.9500 . ?
C20 C19 1.378(6) . ?
C18 H18 0.9500 . ?
C18 C19 1.397(6) . ?
C19 H19 0.9500 . ?
C5 H5A 0.9800 . ?
C5 H5B 0.9800 . ?
C5 H5C 0.9800 . ?
