#------------------------------------------------------------------------------
#$Date: 2025-08-22 18:52:37 +0300 (Fri, 22 Aug 2025) $
#$Revision: 301865 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/22/07/7220781.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_7220781
loop_
_publ_author_name
'Zhang, Jun'
'Lin, Xiuping'
'Li, Liangchun'
'Zhong, Baliang'
'liao, xiaojian'
'Liu, Yonghong'
'xu, shihai'
_publ_section_title
;
 Gliomasolides A-E, Unusual Macrolides from a Sponge-Derived Fungus
 Gliomastix sp. ZSDS1-F7-2
;
_journal_name_full               'RSC Adv.'
_journal_paper_doi               10.1039/C5RA08559D
_journal_year                    2015
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C18 H32 O4'
_chemical_formula_sum            'C18 H32 O4'
_chemical_formula_weight         312.44
_chemical_name_systematic        'gliomasolide A'
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2014-09-18
_audit_creation_method
;
  Olex2 1.2-beta
  (compiled May  9 2012 12:37:22, GUI svn.r4230)
;
_audit_update_record
;
2015-03-31 deposited with the CCDC.
2015-06-09 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 91.546(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   5.42511(18)
_cell_length_b                   7.6161(2)
_cell_length_c                   21.7672(8)
_cell_measurement_reflns_used    2971
_cell_measurement_temperature    99.9(4)
_cell_measurement_theta_max      75.6320
_cell_measurement_theta_min      6.1140
_cell_volume                     899.05(5)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_molecular_graphics
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement
;
XL, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution
;
SHELXS, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_diffrn_ambient_temperature      99.9(4)
_diffrn_detector_area_resol_mean 10.3587
_diffrn_measured_fraction_theta_full 0.9961
_diffrn_measured_fraction_theta_max 0.8605
_diffrn_measurement_details
;
  1 omega   33.00   90.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      110.5703  -30.0000    0.0000 57

  2 omega  -49.00   35.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.8203   37.0000 -120.0000 84

  3 omega  -90.00    7.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.8203  112.0000  -47.0000 97

  4 omega -114.00  -11.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.8203  -57.0000   90.0000 103

  5 omega   33.00   81.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      110.5703  -30.0000  150.0000 48

  6 omega   44.00   98.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      110.5703  -45.0000  -90.0000 54

  7 omega   35.00   90.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      110.5703  -30.0000 -150.0000 55

  8 omega   86.00  133.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      110.5703   45.0000   30.0000 47

  9 omega   56.00  115.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      110.5703 -111.0000  -30.0000 59

 10 omega  143.00  171.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      110.5703   45.0000   30.0000 28

 11 omega   37.00  145.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      110.5703  -15.0000   30.0000 108

 12 omega   49.00  137.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      110.5703  -77.0000    0.0000 88

 13 omega   35.00  130.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      110.5703  -77.0000  150.0000 95
;
_diffrn_measurement_device       'kappa diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.1989745000
_diffrn_orient_matrix_UB_12      0.1433231000
_diffrn_orient_matrix_UB_13      -0.0049049000
_diffrn_orient_matrix_UB_21      0.0176549000
_diffrn_orient_matrix_UB_22      -0.0370320000
_diffrn_orient_matrix_UB_23      -0.0692876000
_diffrn_orient_matrix_UB_31      -0.2019834000
_diffrn_orient_matrix_UB_32      0.1379461000
_diffrn_orient_matrix_UB_33      -0.0135856000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.5418
_diffrn_reflns_av_R_equivalents  0.0271
_diffrn_reflns_av_unetI/netI     0.0307
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            4417
_diffrn_reflns_theta_full        66.50
_diffrn_reflns_theta_max         67.49
_diffrn_reflns_theta_min         6.10
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_current           0.80
_diffrn_source_power             0.040
_diffrn_source_target            Cu
_diffrn_source_voltage           50
_exptl_absorpt_coefficient_mu    0.635
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.61519
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.154
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             344
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.351
_refine_diff_density_min         -0.178
_refine_diff_density_rms         0.052
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.0(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.001
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     204
_refine_ls_number_reflns         2760
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.000
_refine_ls_R_factor_all          0.0457
_refine_ls_R_factor_gt           0.0445
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0790P)²+0.2238P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1137
_refine_ls_wR_factor_ref         0.1151
_reflns_number_gt                2686
_reflns_number_total             2760
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c5ra08559d2.cif
_cod_data_source_block           zjun2cult
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to
/usr/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 3271 2015-04-21 07:52:19Z andrius 
;
_cod_original_sg_symbol_H-M      P2(1)
_cod_database_code               7220781
_chemical_oxdiff_formula         'C18 O4 H30'
_reflns_odcompleteness_completeness 99.61
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     68.13
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
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
O1 O 0.4447(3) 0.4013(2) 0.24258(6) 0.0218(3) Uani 1 1 d .
O2 O 0.0417(3) 0.4076(3) 0.26479(7) 0.0320(4) Uani 1 1 d .
O4 O 0.8656(3) 0.3333(2) 0.44810(7) 0.0211(3) Uani 1 1 d .
H4 H 0.8379 0.2248 0.4488 0.047(10) Uiso 1 1 calc R
O7 O 0.8486(3) 0.9771(2) 0.45522(7) 0.0222(3) Uani 1 1 d .
H7 H 0.9338 0.9448 0.4860 0.039(8) Uiso 1 1 calc R
C1 C 0.2563(4) 0.3925(3) 0.28051(10) 0.0215(4) Uani 1 1 d .
C2 C 0.3383(4) 0.3726(3) 0.34562(9) 0.0204(4) Uani 1 1 d .
H2 H 0.2206 0.3384 0.3749 0.024 Uiso 1 1 calc R
C3 C 0.5690(4) 0.4006(3) 0.36479(9) 0.0209(4) Uani 1 1 d .
H3 H 0.6938 0.4055 0.3350 0.025 Uiso 1 1 calc R
C4 C 0.6427(4) 0.4250(3) 0.43133(9) 0.0206(4) Uani 1 1 d .
H4A H 0.5062 0.3840 0.4578 0.025 Uiso 1 1 calc R
C5 C 0.6935(4) 0.6214(3) 0.44364(9) 0.0201(4) Uani 1 1 d .
H5A H 0.5501 0.6910 0.4285 0.024 Uiso 1 1 calc R
H5B H 0.7120 0.6406 0.4885 0.024 Uiso 1 1 calc R
C6 C 0.9271(4) 0.6871(3) 0.41223(10) 0.0202(5) Uani 1 1 d .
H6A H 1.0731 0.6549 0.4381 0.024 Uiso 1 1 calc R
H6B H 0.9413 0.6264 0.3723 0.024 Uiso 1 1 calc R
C7 C 0.9295(4) 0.8851(3) 0.40130(9) 0.0213(4) Uani 1 1 d .
H7A H 1.1022 0.9220 0.3929 0.026 Uiso 1 1 calc R
C8 C 0.7631(4) 0.9416(3) 0.34744(10) 0.0231(5) Uani 1 1 d .
H8A H 0.7320 1.0693 0.3505 0.028 Uiso 1 1 calc R
H8B H 0.6026 0.8807 0.3502 0.028 Uiso 1 1 calc R
C9 C 0.8720(4) 0.9020(3) 0.28497(9) 0.0248(4) Uani 1 1 d .
H9A H 0.9255 0.7778 0.2839 0.030 Uiso 1 1 calc R
H9B H 1.0190 0.9767 0.2793 0.030 Uiso 1 1 calc R
C10 C 0.6842(4) 0.9357(3) 0.23203(9) 0.0259(5) Uani 1 1 d .
H10A H 0.5952 1.0465 0.2401 0.031 Uiso 1 1 calc R
H10B H 0.7739 0.9509 0.1934 0.031 Uiso 1 1 calc R
C11 C 0.4964(4) 0.7874(3) 0.22352(10) 0.0250(5) Uani 1 1 d .
H11A H 0.4603 0.7377 0.2643 0.030 Uiso 1 1 calc R
H11B H 0.3411 0.8371 0.2061 0.030 Uiso 1 1 calc R
C12 C 0.5814(4) 0.6394(3) 0.18178(9) 0.0233(5) Uani 1 1 d .
H12A H 0.5927 0.6844 0.1393 0.028 Uiso 1 1 calc R
H12B H 0.7481 0.6007 0.1955 0.028 Uiso 1 1 calc R
C13 C 0.4070(4) 0.4821(3) 0.18193(10) 0.0223(4) Uani 1 1 d .
H13 H 0.2327 0.5238 0.1772 0.027 Uiso 1 1 calc R
C14 C 0.4571(4) 0.3432(3) 0.13364(10) 0.0251(5) Uani 1 1 d .
H14A H 0.4680 0.4008 0.0930 0.030 Uiso 1 1 calc R
H14B H 0.6184 0.2876 0.1433 0.030 Uiso 1 1 calc R
C15 C 0.2598(4) 0.2016(3) 0.12985(10) 0.0243(5) Uani 1 1 d .
H15A H 0.0992 0.2568 0.1191 0.029 Uiso 1 1 calc R
H15B H 0.2457 0.1462 0.1708 0.029 Uiso 1 1 calc R
C16 C 0.3136(4) 0.0593(3) 0.08257(11) 0.0273(5) Uani 1 1 d .
H16A H 0.3336 0.1152 0.0420 0.033 Uiso 1 1 calc R
H16B H 0.4715 0.0014 0.0942 0.033 Uiso 1 1 calc R
C17 C 0.1127(4) -0.0795(4) 0.07704(10) 0.0295(5) Uani 1 1 d .
H17A H -0.0459 -0.0212 0.0665 0.035 Uiso 1 1 calc R
H17B H 0.0956 -0.1373 0.1174 0.035 Uiso 1 1 calc R
C18 C 0.1625(5) -0.2199(4) 0.02873(13) 0.0411(7) Uani 1 1 d .
H18A H 0.1660 -0.1652 -0.0120 0.062 Uiso 1 1 calc R
H18B H 0.0317 -0.3085 0.0292 0.062 Uiso 1 1 calc R
H18C H 0.3219 -0.2758 0.0380 0.062 Uiso 1 1 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 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
C1 O1 C13 119.21(15)
O1 C1 C2 112.48(17)
O2 C1 O1 124.62(19)
O2 C1 C2 122.80(19)
C3 C2 C1 122.74(19)
C2 C3 C4 123.17(18)
O4 C4 C3 112.66(17)
O4 C4 C5 106.40(17)
C3 C4 C5 109.17(18)
C6 C5 C4 112.52(17)
C7 C6 C5 113.63(17)
O7 C7 C6 110.38(17)
O7 C7 C8 107.55(17)
C8 C7 C6 113.07(18)
C7 C8 C9 113.22(18)
C8 C9 C10 111.68(19)
C11 C10 C9 113.14(18)
C12 C11 C10 114.01(19)
C13 C12 C11 112.39(18)
O1 C13 C12 105.06(17)
O1 C13 C14 107.86(18)
C14 C13 C12 114.96(18)
C15 C14 C13 113.12(18)
C14 C15 C16 113.14(18)
C17 C16 C15 113.37(19)
C16 C17 C18 113.6(2)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C1 1.333(2)
O1 C13 1.466(3)
O2 C1 1.210(3)
O4 C4 1.435(3)
O7 C7 1.445(3)
C1 C2 1.482(3)
C2 C3 1.326(3)
C3 C4 1.504(3)
C4 C5 1.543(3)
C5 C6 1.540(3)
C6 C7 1.527(3)
C7 C8 1.522(3)
C8 C9 1.527(3)
C9 C10 1.539(3)
C10 C11 1.529(3)
C11 C12 1.527(3)
C12 C13 1.526(3)
C13 C14 1.521(3)
C14 C15 1.520(3)
C15 C16 1.528(3)
C16 C17 1.521(3)
C17 C18 1.529(4)
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O4 H4 O7 0.84 1.89 2.719(2) 167.6 1_545
O7 H7 O4 0.84 1.97 2.803(2) 171.1 2_756
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
O1 C1 C2 C3 14.3(3)
O1 C13 C14 C15 70.8(2)
O2 C1 C2 C3 -162.3(2)
O4 C4 C5 C6 52.8(2)
O7 C7 C8 C9 161.94(18)
C1 O1 C13 C12 118.3(2)
C1 O1 C13 C14 -118.6(2)
C1 C2 C3 C4 164.4(2)
C2 C3 C4 O4 137.9(2)
C2 C3 C4 C5 -104.2(2)
C3 C4 C5 C6 -69.0(2)
C4 C5 C6 C7 157.03(17)
C5 C6 C7 O7 44.3(2)
C5 C6 C7 C8 -76.2(2)
C6 C7 C8 C9 -75.9(2)
C7 C8 C9 C10 171.66(19)
C8 C9 C10 C11 -78.9(2)
C9 C10 C11 C12 -87.1(2)
C10 C11 C12 C13 171.55(17)
C11 C12 C13 O1 -71.2(2)
C11 C12 C13 C14 170.38(18)
C12 C13 C14 C15 -172.43(18)
C13 O1 C1 O2 18.3(3)
C13 O1 C1 C2 -158.2(2)
C13 C14 C15 C16 -178.43(19)
C14 C15 C16 C17 -178.07(19)
C15 C16 C17 C18 178.6(2)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139200424
