#------------------------------------------------------------------------------
#$Date: 2021-09-06 15:25:28 +0300 (Mon, 06 Sep 2021) $
#$Revision: 268921 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/15/81/7158134.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_7158134
loop_
_publ_author_name
'Wang, Lu'
'Huang, Yanbing'
'Zhang, Liping'
'Liu, Zhiwen'
'Liu, Wei'
'Xu, Huixin'
'Zhang, Qingbo'
'Zhang, Haibo'
'Yan, Yan'
'Liu, Zhiyong'
'Zhang, Tianyu'
'Zhang, Wenjun'
'Zhang, Changsheng'
_publ_section_title
;
 Structures and absolute configurations of phomalones from the
 coral-associated fungus Parengyodontium album sp. SCSIO 40430.
;
_journal_issue                   27
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              6030
_journal_page_last               6037
_journal_paper_doi               10.1039/d1ob00869b
_journal_volume                  19
_journal_year                    2021
_chemical_formula_moiety         'C11.95 H13.91 O4'
_chemical_formula_sum            'C12 H14 O4'
_chemical_formula_weight         222.23
_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
_atom_sites_solution_primary     dual
_audit_creation_date             2019-03-19
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2021-03-22 deposited with the CCDC.	2021-06-21 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 115.015(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   15.6505(4)
_cell_length_b                   4.35190(10)
_cell_length_c                   17.2668(5)
_cell_measurement_reflns_used    2179
_cell_measurement_temperature    99.9(5)
_cell_measurement_theta_max      73.6490
_cell_measurement_theta_min      6.4150
_cell_volume                     1065.72(6)
_computing_cell_refinement       'CrysAlisPro 1.171.39.33c (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.33c (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.33c (Rigaku OD, 2017)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      99.9(5)
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.963
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -14.00  31.00   0.50    1.00    --    0.00 -82.00 -30.00   90
  2  ω    -29.00  31.00   0.50    1.00    --    0.00 -82.00-150.00  120
  3  ω     -1.00  28.00   0.50    1.00    --    0.00 -82.00 120.00   58
  4  ω    -30.00  -3.00   0.50    1.00    --    0.00 -82.00 120.00   54
  5  ω    160.00 185.00   0.50    4.00    --   95.20  15.00 120.00   50
  6  ω     77.00 109.00   0.50    4.00    --   95.20 -45.00 -90.00   64
  7  ω     97.00 123.00   0.50    4.00    --   95.20  15.00 120.00   52
  8  ω      9.00 100.00   0.50    4.00    --   95.20 -45.00  30.00  182
  9  ω     79.00 181.00   0.50    4.00    --   95.20  61.00 150.00  204
 10  ω    133.00 183.00   0.50    4.00    --   95.20  82.00  30.00  100
 11  ω      7.00  73.00   0.50    4.00    --   95.20 -45.00 -90.00  132
 12  ω     17.00 106.00   0.50    4.00    --   95.20 -30.00  30.00  178
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC12 (RINC): Kappa single'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0974018000
_diffrn_orient_matrix_UB_12      -0.0728837000
_diffrn_orient_matrix_UB_13      -0.0722647000
_diffrn_orient_matrix_UB_21      0.0135230000
_diffrn_orient_matrix_UB_22      0.2590769000
_diffrn_orient_matrix_UB_23      -0.0545677000
_diffrn_orient_matrix_UB_31      0.0461568000
_diffrn_orient_matrix_UB_32      -0.2300031000
_diffrn_orient_matrix_UB_33      -0.0385916000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0236
_diffrn_reflns_av_unetI/netI     0.0384
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.963
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       3
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            4622
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.963
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.018
_diffrn_reflns_theta_min         5.175
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.865
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.87085
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.33c (Rigaku Oxford Diffraction, 2017)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear yellowish white'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   yellowish
_exptl_crystal_colour_primary    white
_exptl_crystal_density_diffrn    1.385
_exptl_crystal_description       block
_exptl_crystal_F_000             472
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.874
_refine_diff_density_min         -0.269
_refine_diff_density_rms         0.053
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.077
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     151
_refine_ls_number_reflns         2097
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.077
_refine_ls_R_factor_all          0.0554
_refine_ls_R_factor_gt           0.0475
_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)+(0.0682P)²+0.5610P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1307
_refine_ls_wR_factor_ref         0.1367
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1783
_reflns_number_total             2097
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d1ob00869b2.cif
_cod_data_source_block           zhangwenjun_sh31-19_collect
_cod_depositor_comments
'Adding full bibliography for 7158134--7158138.cif.'
_cod_database_code               7158134
_shelx_shelxl_version_number     2018/1
_chemical_oxdiff_formula         'C44 H52 O20 '
_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   0.958
_shelx_estimated_absorpt_t_min   0.846
_reflns_odcompleteness_completeness 99.77
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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, All O(H) groups
2. Others
 Sof(H16a)=Sof(H16b)=Sof(H16c)=Sof(H2a)=Sof(H2b)=FVAR(1)
 Sof(C1)=Sof(H1)=FVAR(2)
3.a Ternary CH refined with riding coordinates:
 C1(H1)
3.b Secondary CH2 refined with riding coordinates:
 C14(H14a,H14b), C2(H2a,H2b)
3.c Aromatic/amide H refined with riding coordinates:
 C6(H6)
3.d Idealised Me refined as rotating group:
 C15(H15a,H15b,H15c), C16(H16a,H16b,H16c)
3.e Idealised tetrahedral OH refined as rotating group:
 O12(H12), O11(H11)
;
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.338
_oxdiff_exptl_absorpt_empirical_full_min 0.788
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
O10 O 0.81525(8) 0.3721(3) 0.70392(7) 0.0229(3) Uani 1 1 d . . . . .
O12 O 0.66583(8) 0.3455(3) 0.88909(7) 0.0245(3) Uani 1 1 d . . . . .
H12 H 0.615065 0.383472 0.890252 0.037 Uiso 1 1 calc GR . . . .
O11 O 0.52427(8) 0.9222(3) 0.63305(7) 0.0263(3) Uani 1 1 d . . . . .
H11 H 0.532203 0.961681 0.590106 0.039 Uiso 1 1 calc GR . . . .
O13 O 0.60884(8) 0.9178(3) 0.53192(8) 0.0336(4) Uani 1 1 d . . . . .
C7 C 0.66449(11) 0.4464(4) 0.81418(10) 0.0197(4) Uani 1 1 d . . . . .
C9 C 0.74069(10) 0.4603(4) 0.72088(10) 0.0195(4) Uani 1 1 d . . . . .
C5 C 0.59517(11) 0.7402(4) 0.68551(10) 0.0209(4) Uani 1 1 d . . . . .
C8 C 0.73958(10) 0.3494(4) 0.79547(10) 0.0192(4) Uani 1 1 d . . . . .
C6 C 0.59367(11) 0.6408(4) 0.76074(10) 0.0212(4) Uani 1 1 d . . . . .
H6 H 0.545741 0.703327 0.775575 0.025 Uiso 1 1 calc R . . . .
C4 C 0.66892(10) 0.6519(4) 0.66321(10) 0.0204(4) Uani 1 1 d . . . . .
C14 C 0.81775(11) 0.1519(4) 0.85711(10) 0.0217(4) Uani 1 1 d . . . . .
H14A H 0.842638 0.023848 0.825465 0.026 Uiso 1 1 calc R . . . .
H14B H 0.792526 0.017729 0.887235 0.026 Uiso 1 1 calc R . . . .
C3 C 0.67079(11) 0.7516(4) 0.58414(10) 0.0252(4) Uani 1 1 d . . . . .
C15 C 0.89725(12) 0.3438(4) 0.92169(11) 0.0284(4) Uani 1 1 d . . . . .
H15A H 0.924708 0.468661 0.892311 0.043 Uiso 1 1 calc GR . . . .
H15B H 0.944526 0.210383 0.961067 0.043 Uiso 1 1 calc GR . . . .
H15C H 0.872656 0.473571 0.952446 0.043 Uiso 1 1 calc GR . . . .
C16 C 0.91974(13) 0.4405(5) 0.63842(13) 0.0344(5) Uani 1 1 d . . . . .
H16A H 0.970969 0.406486 0.693372 0.052 Uiso 0.99(2) 1 calc GR . P A 1
H16B H 0.939584 0.578732 0.605885 0.052 Uiso 0.99(2) 1 calc GR . P A 1
H16C H 0.901024 0.248383 0.608645 0.052 Uiso 0.99(2) 1 calc GR . P A 1
C2 C 0.75239(13) 0.6364(5) 0.56769(12) 0.0324(5) Uani 1 1 d . . . . .
H2A H 0.734487 0.447437 0.534942 0.039 Uiso 0.99(2) 1 calc R . P A 1
H2B H 0.767921 0.787141 0.534267 0.039 Uiso 0.99(2) 1 calc R . P A 1
C1 C 0.83717(13) 0.5790(5) 0.65003(12) 0.0277(6) Uani 0.950(8) 1 d . . P B 1
H1 H 0.857373 0.775265 0.680103 0.033 Uiso 0.950(8) 1 calc R . P B 1
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 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 0.0492 0.0322 '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 O10 C1 114.86(13) . . ?
C7 O12 H12 109.5 . . ?
C5 O11 H11 109.5 . . ?
O12 C7 C8 116.31(14) . . ?
O12 C7 C6 121.09(14) . . ?
C6 C7 C8 122.58(14) . . ?
O10 C9 C8 116.61(14) . . ?
O10 C9 C4 120.53(14) . . ?
C8 C9 C4 122.85(14) . . ?
O11 C5 C6 118.61(14) . . ?
O11 C5 C4 120.60(14) . . ?
C6 C5 C4 120.79(15) . . ?
C7 C8 C14 121.07(14) . . ?
C9 C8 C7 116.71(14) . . ?
C9 C8 C14 122.10(14) . . ?
C7 C6 H6 120.3 . . ?
C5 C6 C7 119.35(14) . . ?
C5 C6 H6 120.3 . . ?
C9 C4 C5 117.66(14) . . ?
C9 C4 C3 120.98(14) . . ?
C5 C4 C3 121.35(14) . . ?
C8 C14 H14A 109.2 . . ?
C8 C14 H14B 109.2 . . ?
C8 C14 C15 111.89(14) . . ?
H14A C14 H14B 107.9 . . ?
C15 C14 H14A 109.2 . . ?
C15 C14 H14B 109.2 . . ?
O13 C3 C4 122.72(15) . . ?
O13 C3 C2 121.44(15) . . ?
C4 C3 C2 115.84(14) . . ?
C14 C15 H15A 109.5 . . ?
C14 C15 H15B 109.5 . . ?
C14 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C1 C16 H16A 109.5 . . ?
C1 C16 H16B 109.5 . . ?
C1 C16 H16C 109.5 . . ?
C3 C2 H2A 109.4 . . ?
C3 C2 H2B 109.4 . . ?
H2A C2 H2B 108.0 . . ?
C1 C2 C3 110.95(14) . . ?
C1 C2 H2A 109.4 . . ?
C1 C2 H2B 109.4 . . ?
O10 C1 C16 106.69(15) . . ?
O10 C1 C2 111.14(15) . . ?
O10 C1 H1 108.4 . . ?
C16 C1 H1 108.4 . . ?
C2 C1 C16 113.79(15) . . ?
C2 C1 H1 108.4 . . ?
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
O10 C9 1.3725(19) . ?
O10 C1 1.437(2) . ?
O12 H12 0.8200 . ?
O12 C7 1.3575(18) . ?
O11 H11 0.8200 . ?
O11 C5 1.3525(19) . ?
O13 C3 1.240(2) . ?
C7 C8 1.409(2) . ?
C7 C6 1.390(2) . ?
C9 C8 1.382(2) . ?
C9 C4 1.415(2) . ?
C5 C6 1.379(2) . ?
C5 C4 1.416(2) . ?
C8 C14 1.506(2) . ?
C6 H6 0.9300 . ?
C4 C3 1.444(2) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C14 C15 1.522(2) . ?
C3 C2 1.506(2) . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C16 C1 1.514(2) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C2 C1 1.500(3) . ?
C1 H1 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
O10 C9 C8 C7 178.32(14) . . . . ?
O10 C9 C8 C14 2.3(2) . . . . ?
O10 C9 C4 C5 -178.56(14) . . . . ?
O10 C9 C4 C3 1.9(2) . . . . ?
O12 C7 C8 C9 -177.65(14) . . . . ?
O12 C7 C8 C14 -1.6(2) . . . . ?
O12 C7 C6 C5 179.51(15) . . . . ?
O11 C5 C6 C7 178.14(15) . . . . ?
O11 C5 C4 C9 -179.79(15) . . . . ?
O11 C5 C4 C3 -0.2(3) . . . . ?
O13 C3 C2 C1 152.48(18) . . . . ?
C7 C8 C14 C15 -88.41(18) . . . . ?
C9 O10 C1 C16 -179.43(14) . . . . ?
C9 O10 C1 C2 -54.9(2) . . . . ?
C9 C8 C14 C15 87.41(19) . . . . ?
C9 C4 C3 O13 179.54(16) . . . . ?
C9 C4 C3 C2 0.6(2) . . . . ?
C5 C4 C3 O13 0.0(3) . . . . ?
C5 C4 C3 C2 -178.98(16) . . . . ?
C8 C7 C6 C5 1.2(3) . . . . ?
C8 C9 C4 C5 2.3(2) . . . . ?
C8 C9 C4 C3 -177.25(15) . . . . ?
C6 C7 C8 C9 0.8(2) . . . . ?
C6 C7 C8 C14 176.79(15) . . . . ?
C6 C5 C4 C9 -0.3(2) . . . . ?
C6 C5 C4 C3 179.30(16) . . . . ?
C4 C9 C8 C7 -2.5(2) . . . . ?
C4 C9 C8 C14 -178.51(15) . . . . ?
C4 C5 C6 C7 -1.4(3) . . . . ?
C4 C3 C2 C1 -28.5(2) . . . . ?
C3 C2 C1 O10 55.3(2) . . . . ?
C3 C2 C1 C16 175.73(17) . . . . ?
C1 O10 C9 C8 -154.87(15) . . . . ?
C1 O10 C9 C4 25.9(2) . . . . ?
