#------------------------------------------------------------------------------
#$Date: 2025-11-12 03:11:57 +0100 (Wed 12 de Nov de 2025) $
#$Revision: 303273 $
#$URL: svn://www.crystallography.net/cod/cif/7/16/08/7160847.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_7160847
loop_
_publ_author_name
'Li, Wanpeng'
'Gao, Ying'
'Ruan, Hanli'
_publ_section_title
;
 Resorcylic Acid Lactone Derivatives with Immunosuppressive Activity from
 the Endophytic Podospora sp. G214
;
_journal_name_full               'Organic & Biomolecular Chemistry'
_journal_paper_doi               10.1039/D5OB01602A
_journal_year                    2025
_chemical_formula_moiety         'C13 H12 Cl2 O5'
_chemical_formula_sum            'C13 H12 Cl2 O5'
_chemical_formula_weight         319.13
_space_group_crystal_system      monoclinic
_space_group_IT_number           11
_space_group_name_Hall           '-P 2yb'
_space_group_name_H-M_alt        'P 1 21/m 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_audit_creation_date             2020-09-14
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2025-10-09 deposited with the CCDC.	2025-11-11 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 99.933(5)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   9.4456(5)
_cell_length_b                   6.6650(3)
_cell_length_c                   10.5231(5)
_cell_measurement_reflns_used    3860
_cell_measurement_temperature    99.99(10)
_cell_measurement_theta_max      73.6160
_cell_measurement_theta_min      4.7340
_cell_volume                     652.55(6)
_computing_cell_refinement       'CrysAlisPro 1.171.39.28b (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.39.28b (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.39.28b (Rigaku OD, 2015)'
_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_environment      N~2~
_diffrn_ambient_temperature      99.99(10)
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     41.00 104.00   0.50    0.50    --   95.20 -23.00 114.00  126
  2  ω    106.00 132.00   0.50    0.50    --   95.20  23.00 -80.00   52
  3  ω    135.00 162.00   0.50    0.50    --   95.20  23.00 -80.00   54
  4  ω     12.00  37.00   0.50    0.50    --   95.20 -23.00 114.00   50
  5  ω    -43.00  20.00   0.50    0.50    --    0.00 -57.00 -60.00  126
  6  ω    -28.00  31.00   0.50    0.50    --    0.00 -82.00   0.00  118
  7  ω    -19.00   6.00   0.50    0.50    --    0.00 -82.00-120.00   50
  8  ω      1.00  29.00   0.50    0.50    --    0.00 -82.00  60.00   56
  9  ω     12.00  37.00   0.50    0.50    --    0.00  23.00 -80.00   50
 10  ω    -59.00 -34.00   0.50    0.50    --    0.00 -23.00 114.00   50
 11  ω    -16.00  10.00   0.50    0.50    --    0.00  57.00-150.00   52
 12  ω    -89.00 -61.00   0.50    0.50    --    0.00 -57.00 -60.00   56
 13  ω    123.00 185.00   0.50    0.50    --   95.20  61.00  30.00  124
 14  ω    120.00 184.00   0.50    0.50    --   95.20  61.00  90.00  128
 15  ω     72.00  98.00   0.50    0.50    --   95.20  61.00  30.00   52
 16  ω     73.00  99.00   0.50    0.50    --   95.20  61.00   8.31   52
 17  ω     74.00 101.00   0.50    0.50    --   95.20  57.00 -27.96   54
 18  ω     36.00  91.00   0.50    0.50    --   95.20 -77.00  30.00  110
 19  ω      8.00 117.00   0.50    0.50    --   95.20 -61.00 -30.00  218
 20  ω     75.00 108.00   0.50    0.50    --   95.20  61.00  90.00   66
 21  ω     73.00  98.00   0.50    0.50    --   95.20  61.00   0.00   50
 22  ω     80.00 105.00   0.50    0.50    --   95.20  45.00   0.00   50
 23  ω    158.00 185.00   0.50    0.50    --   95.20  61.00  60.00   54
 24  ω     81.00 144.00   0.50    0.50    --   95.20  45.00  60.00  126
 25  ω    147.00 180.00   0.50    0.50    --   95.20  45.00  60.00   66
 26  ω    111.00 136.00   0.50    0.50    --   95.20  74.00  63.20   50
 27  ω     80.00 107.00   0.50    0.50    --   95.20  45.00 -30.00   54
 28  ω    124.00 159.00   0.50    0.50    --   95.20  45.00 -30.00   70
 29  ω     83.00 118.00   0.50    0.50    --   95.20  45.00  30.00   70
 30  ω     77.00 104.00   0.50    0.50    --   95.20  53.00   2.45   54
 31  ω     74.00 100.00   0.50    0.50    --   95.20  61.00 -60.00   52
 32  ω    119.00 144.00   0.50    0.50    --   95.20  61.00 -60.00   50
 33  ω     75.00 118.00   0.50    0.50    --   95.20 -82.00-120.00   86
 34  ω     67.00  93.00   0.50    0.50    --   95.20  74.00  63.20   52
 35  ω     73.00  98.00   0.50    0.50    --   95.20  61.00 -30.00   50
 36  ω     79.00 175.00   0.50    0.50    --   95.20  30.00   0.00  192
 37  ω     80.00 105.00   0.50    0.50    --   95.20  30.00 -30.00   50
 38  ω     33.00 107.00   0.50    0.50    --   95.20 -30.00 -60.00  148
 39  ω     72.00 103.00   0.50    0.50    --   95.20  61.00  60.00   62
;
_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      -0.1551486000
_diffrn_orient_matrix_UB_12      0.0663748000
_diffrn_orient_matrix_UB_13      -0.0528369000
_diffrn_orient_matrix_UB_21      -0.0295198000
_diffrn_orient_matrix_UB_22      0.0203190000
_diffrn_orient_matrix_UB_23      0.1389163000
_diffrn_orient_matrix_UB_31      0.0495470000
_diffrn_orient_matrix_UB_32      0.2205146000
_diffrn_orient_matrix_UB_33      0.0030197000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0572
_diffrn_reflns_av_unetI/netI     0.0250
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            6109
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        65.933
_diffrn_reflns_theta_max         65.933
_diffrn_reflns_theta_min         4.265
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    4.651
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.40851
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.28b (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.624
_exptl_crystal_description       block
_exptl_crystal_F_000             328
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.692
_refine_diff_density_min         -0.682
_refine_diff_density_rms         0.124
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.206
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     123
_refine_ls_number_reflns         1238
_refine_ls_number_restraints     6
_refine_ls_restrained_S_all      1.206
_refine_ls_R_factor_all          0.0993
_refine_ls_R_factor_gt           0.0981
_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)+(0.0260P)²+6.9787P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2145
_refine_ls_wR_factor_ref         0.2149
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1201
_reflns_number_total             1238
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d5ob01602a2.cif
_cod_data_source_block           20200911_tof-112
_cod_database_code               7160847
_shelx_shelxl_version_number     2014/7
_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   0.801
_shelx_estimated_absorpt_t_min   0.336
_reflns_odcompleteness_completeness 99.45
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, {H9A,H9B} of C9
 At 1.5 times of:
  All O(H) groups, {H12A,H12B} of C12
2. Uiso/Uaniso restraints and constraints
Uanis(C12) \\sim Ueq: with sigma of 0.005 and sigma for terminal atoms of 0.01
3. Others
 Fixed Sof: H9A(0.5) H9B(0.5) H10(0.5) H12A(0.5) H4A(0.5) O5(0.5) H5A(0.5)
4.a Riding coordinates:
 C12(H12A,H12B)
4.b Ternary CH refined with riding coordinates:
 C10(H10), C11(H11)
4.c Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B)
4.d Aromatic/amide H refined with riding coordinates:
 C4(H4), C5(H5), C7(H7)
4.e Idealised tetrahedral OH refined as rotating group:
 O4(H4A), O5(H5A)
;
_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 2.123
_oxdiff_exptl_absorpt_empirical_full_min 0.536
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'
'-x, -y, -z'
'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_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 -0.0516(9) 0.7500 1.0656(8) 0.0229(19) Uani 1 2 d S T P . .
C3 C 0.2062(9) 0.7500 1.0966(8) 0.0232(19) Uani 1 2 d S T P . .
C4 C 0.2074(9) 0.7500 0.9682(8) 0.0214(19) Uani 1 2 d S T P . .
H4 H 0.2966 0.7500 0.9379 0.026 Uiso 1 2 calc RS T P . .
C4A C 0.0746(9) 0.7500 0.8767(8) 0.0206(18) Uani 1 2 d S T P . .
C5 C 0.0733(10) 0.7500 0.7445(8) 0.0221(19) Uani 1 2 d S T P . .
H5 H 0.1603 0.7500 0.7106 0.027 Uiso 1 2 calc RS T P . .
C6 C -0.0607(9) 0.7500 0.6627(7) 0.0198(18) Uani 1 2 d S T P . .
C7 C -0.1891(9) 0.7500 0.7101(8) 0.0217(18) Uani 1 2 d S T P . .
H7 H -0.2782 0.7500 0.6522 0.026 Uiso 1 2 calc RS T P . .
C8 C -0.1870(9) 0.7500 0.8412(8) 0.0229(19) Uani 1 2 d S T P . .
C8A C -0.0530(10) 0.7500 0.9267(8) 0.0225(19) Uani 1 2 d S T P . .
C9 C 0.3312(9) 0.7500 1.2044(7) 0.0214(18) Uani 1 2 d S T P B .
H9A H 0.3238 0.6303 1.2586 0.026 Uiso 0.5 1 calc R . . . .
H9B H 0.3238 0.8697 1.2586 0.026 Uiso 0.5 1 calc R . . . .
C10 C 0.4782(10) 0.7500 1.1665(9) 0.032(2) Uani 1 2 d S T P . .
H10 H 0.4873 0.8729 1.1140 0.038 Uiso 0.5 1 calc R . . B .
C11 C 0.6006(10) 0.7500 1.2830(8) 0.033(2) Uani 1 2 d S T P B .
H11 H 0.6939 0.7500 1.2503 0.040 Uiso 1 2 calc RS T P . .
C12 C 0.0520(10) 0.7500 0.4747(8) 0.026(2) Uani 1 2 d S TU P . .
H12A H 0.0261 0.7354 0.3809 0.039 Uiso 0.5 1 d R . . A -1
H12B H 0.1138 0.6379 0.5099 0.039 Uiso 1 1 d R . . A -1
Cl1 Cl 0.5946(2) 0.5326(4) 1.3782(2) 0.0600(8) Uani 1 1 d . . . . .
O1 O -0.1567(6) 0.7500 1.1170(5) 0.0269(15) Uani 1 2 d S T P . .
O2 O 0.0796(6) 0.7500 1.1431(5) 0.0233(13) Uani 1 2 d S T P . .
O3 O -0.0767(6) 0.7500 0.5314(5) 0.0230(14) Uani 1 2 d S T P . .
O4 O -0.3151(6) 0.7500 0.8848(6) 0.0307(16) Uani 1 2 d S T P . .
H4A H -0.3026 0.7932 0.9609 0.046 Uiso 0.5 1 calc GR . . . .
O5 O 0.5030(9) 0.5778(18) 1.0920(8) 0.038(3) Uani 0.5 1 d . . . B -1
H5A H 0.4430 0.4880 1.1008 0.057 Uiso 0.5 1 calc GR . . 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'
Cl Cl 0.3639 0.7018 '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
O1 C1 C8A 125.5(8) . . ?
O1 C1 O2 117.8(8) . . ?
O2 C1 C8A 116.7(7) . . ?
C4 C3 C9 128.2(8) . . ?
C4 C3 O2 121.0(8) . . ?
O2 C3 C9 110.8(7) . . ?
C3 C4 H4 119.7 . . ?
C3 C4 C4A 120.6(8) . . ?
C4A C4 H4 119.7 . . ?
C5 C4A C4 121.6(8) . . ?
C5 C4A C8A 121.2(8) . . ?
C8A C4A C4 117.1(7) . . ?
C4A C5 H5 121.1 . . ?
C4A C5 C6 117.8(8) . . ?
C6 C5 H5 121.1 . . ?
C7 C6 C5 122.1(7) . . ?
O3 C6 C5 123.5(8) . . ?
O3 C6 C7 114.4(7) . . ?
C6 C7 H7 120.1 . . ?
C8 C7 C6 119.9(8) . . ?
C8 C7 H7 120.1 . . ?
C7 C8 C8A 119.4(8) . . ?
O4 C8 C7 118.4(8) . . ?
O4 C8 C8A 122.1(8) . . ?
C4A C8A C1 121.2(8) . . ?
C4A C8A C8 119.6(8) . . ?
C8 C8A C1 119.1(8) . . ?
C3 C9 H9A 108.2 . . ?
C3 C9 H9B 108.2 . . ?
C3 C9 C10 116.3(7) . . ?
H9A C9 H9B 107.4 . . ?
C10 C9 H9A 108.2 . . ?
C10 C9 H9B 108.2 . . ?
C9 C10 H10 108.5 . . ?
C9 C10 C11 112.9(7) . . ?
C11 C10 H10 108.5 . . ?
O5 C10 C9 113.0(6) . . ?
O5 C10 H10 108.5 . . ?
O5 C10 C11 105.4(6) . . ?
C10 C11 H11 108.2 . . ?
C10 C11 Cl1 111.1(4) . . ?
C10 C11 Cl1 111.1(4) . 4_575 ?
Cl1 C11 H11 108.2 . . ?
Cl1 C11 H11 108.2 4_575 . ?
Cl1 C11 Cl1 110.1(5) 4_575 . ?
H12A C12 H12B 109.5 . . ?
O3 C12 H12A 109.6 . . ?
O3 C12 H12B 109.4 . . ?
C1 O2 C3 123.3(7) . . ?
C6 O3 C12 117.7(6) . . ?
C8 O4 H4A 109.5 . . ?
C10 O5 H5A 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
C1 C8A 1.460(11) . ?
C1 O1 1.209(10) . ?
C1 O2 1.361(10) . ?
C3 C4 1.354(11) . ?
C3 C9 1.490(12) . ?
C3 O2 1.367(10) . ?
C4 H4 0.9500 . ?
C4 C4A 1.444(12) . ?
C4A C5 1.389(11) . ?
C4A C8A 1.396(12) . ?
C5 H5 0.9500 . ?
C5 C6 1.403(12) . ?
C6 C7 1.389(12) . ?
C6 O3 1.363(9) . ?
C7 H7 0.9500 . ?
C7 C8 1.376(11) . ?
C8 C8A 1.421(12) . ?
C8 O4 1.365(10) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C9 C10 1.509(12) . ?
C10 H10 1.0000 . ?
C10 C11 1.534(11) . ?
C10 O5 1.432(11) . ?
C11 H11 1.0000 . ?
C11 Cl1 1.768(5) 4_575 ?
C11 Cl1 1.768(5) . ?
C12 H12A 0.9801 . ?
C12 H12B 0.9800 . ?
C12 O3 1.444(10) . ?
O4 H4A 0.8400 . ?
O5 H5A 0.8400 . ?
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
C3 C4 C4A C5 180.000(4) . . . . ?
C3 C4 C4A C8A 0.000(4) . . . . ?
C3 C9 C10 C11 180.000(4) . . . . ?
C3 C9 C10 O5 -60.5(6) . . . . ?
C4 C3 C9 C10 0.000(5) . . . . ?
C4 C3 O2 C1 0.000(5) . . . . ?
C4 C4A C5 C6 180.000(3) . . . . ?
C4 C4A C8A C1 0.000(4) . . . . ?
C4 C4A C8A C8 180.000(3) . . . . ?
C4A C5 C6 C7 0.000(3) . . . . ?
C4A C5 C6 O3 180.000(2) . . . . ?
C5 C4A C8A C1 180.000(3) . . . . ?
C5 C4A C8A C8 0.000(4) . . . . ?
C5 C6 C7 C8 0.000(3) . . . . ?
C5 C6 O3 C12 0.000(3) . . . . ?
C6 C7 C8 C8A 0.000(3) . . . . ?
C6 C7 C8 O4 180.000(2) . . . . ?
C7 C6 O3 C12 180.000(2) . . . . ?
C7 C8 C8A C1 180.000(3) . . . . ?
C7 C8 C8A C4A 0.000(4) . . . . ?
C8A C1 O2 C3 0.000(5) . . . . ?
C8A C4A C5 C6 0.000(4) . . . . ?
C9 C3 C4 C4A 180.000(4) . . . . ?
C9 C3 O2 C1 180.000(4) . . . . ?
C9 C10 C11 Cl1 61.4(4) . . . . ?
C9 C10 C11 Cl1 -61.4(4) . . . 4_575 ?
O1 C1 C8A C4A 180.000(4) . . . . ?
O1 C1 C8A C8 0.000(4) . . . . ?
O1 C1 O2 C3 180.000(4) . . . . ?
O2 C1 C8A C4A 0.000(4) . . . . ?
O2 C1 C8A C8 180.000(4) . . . . ?
O2 C3 C4 C4A 0.000(5) . . . . ?
O2 C3 C9 C10 180.000(4) . . . . ?
O3 C6 C7 C8 180.000(3) . . . . ?
O4 C8 C8A C1 0.000(4) . . . . ?
O4 C8 C8A C4A 180.000(3) . . . . ?
O5 C10 C11 Cl1 -62.3(9) . . . . ?
O5 C10 C11 Cl1 174.8(6) . . . 4_575 ?
