#------------------------------------------------------------------------------
#$Date: 2022-10-07 04:08:03 +0300 (Fri, 07 Oct 2022) $
#$Revision: 278446 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/06/17/7061776.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_7061776
loop_
_publ_author_name
'Li, Fengli'
'Huang, Zhangyan'
'Mo, Shuyuan'
'Gu, Saisai'
'Zhang, Sitian'
'Yang, Beiye'
'Wang, Jianping'
'Hu, Zhengxi'
'Zhang, Yonghui'
_publ_section_title
;
 Two undescribed pairs of isoprenyl hydroxybenzoic acid derivatives from
 coculture of Pestalotiopsis sp. and Penicillium bialowiezense:
 enantioseparation and their absolute configurations
;
_journal_issue                   36
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              17149
_journal_page_last               17152
_journal_paper_doi               10.1039/D2NJ03531F
_journal_volume                  46
_journal_year                    2022
_chemical_formula_moiety         'C15 H20 O5'
_chemical_formula_sum            'C15 H20 O5'
_chemical_formula_weight         280.31
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2020-08-14
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2021-01-13 deposited with the CCDC.	2022-09-01 downloaded from the CCDC.
;
_cell_angle_alpha                107.096(6)
_cell_angle_beta                 100.136(7)
_cell_angle_gamma                93.672(6)
_cell_formula_units_Z            2
_cell_length_a                   4.9574(5)
_cell_length_b                   11.4656(7)
_cell_length_c                   13.0020(8)
_cell_measurement_reflns_used    4465
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      73.7490
_cell_measurement_theta_min      3.6150
_cell_volume                     690.06(10)
_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    'XM (Sheldrick, 2008)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_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  26.00   0.50    0.50    --    0.00 -77.00 -90.00   80
  2  ω     10.00  38.00   0.50    0.50    --   36.00  72.00  64.93   56
  3  ω    -10.00  53.00   0.50    0.50    --   36.00 -42.00-110.30  126
  4  ω     83.00 128.00   0.50    0.50    --   40.00  72.00 177.05   90
  5  ω     16.00  41.00   0.50    0.50    --   40.00  72.00 177.05   50
  6  ω    106.00 131.00   0.50    0.50    --   44.00  71.00 -75.31   50
  7  ω     18.00  49.00   0.50    0.50    --   44.00  71.00 -75.31   62
  8  ω     30.00  57.00   0.50    2.00    --   52.00  67.00-158.11   54
  9  ω     30.00  71.00   0.50    2.00    --   56.00  71.00 -52.19   82
 10  ω     33.00  58.00   0.50    2.00    --   60.00  73.00-131.62   50
 11  ω     97.00 139.00   0.50    2.00    --   60.00  73.00-131.62   84
 12  ω     33.00  63.00   0.50    2.00    --   60.00  75.00  27.96   60
 13  ω     36.00  76.00   0.50    2.00    --   64.00  74.00  77.36   80
 14  ω     40.00  72.00   0.50    2.00    --   64.00  73.00  54.88   64
 15  ω     40.00  66.00   0.50    2.00    --   68.00  74.00  -5.11   52
 16  ω     43.00  74.00   0.50    2.00    --   68.00  73.00  99.21   62
 17  ω     44.00  81.00   0.50    2.00    --   72.00  74.00 128.81   74
 18  ω     47.00  84.00   0.50    2.00    --   72.00  67.00-115.75   74
 19  ω    118.00 163.00   0.50    2.00    --   76.00  67.00 179.54   90
 20  ω     51.00  87.00   0.50    2.00    --   76.00  67.00 179.54   72
 21  ω    136.00 164.00   0.50    2.00    --   76.00  67.00 -77.27   56
 22  ω     52.00  78.00   0.50    2.00    --   76.00  67.00 -77.27   52
 23  ω     94.00 120.00   0.50    2.00    --   76.00  67.00 -77.27   52
 24  ω     54.00  80.00   0.50    2.00    --   80.00  71.00  -2.98   52
 25  ω    112.00 169.00   0.50    2.00    --   80.00  73.00 -25.65  114
 26  ω     54.00  82.00   0.50    2.00    --   80.00  73.00 -25.65   56
 27  ω     71.00 120.00   0.50    2.00    --   94.60  61.00  60.00   98
 28  ω     74.00 151.00   0.50    2.00    --   94.60  61.00 120.00  154
 29  ω     71.00 134.00   0.50    2.00    --   94.60  61.00 -60.00  126
 30  ω    123.00 184.00   0.50    2.00    --   94.60  61.00  60.00  122
 31  ω     73.00 130.00   0.50    2.00    --   94.60  61.00   0.00  114
 32  ω     92.00 132.00   0.50    2.00    --   94.60  82.00 -60.00   80
 33  ω     90.00 126.00   0.50    2.00    --   94.60 -82.00  30.00   72
 34  ω     36.00  63.00   0.50    2.00    --   94.60 -82.00  30.00   54
 35  ω     72.00 131.00   0.50    2.00    --   94.60  61.00-150.00  118
 36  ω     63.00 115.00   0.50    2.00    --   94.60 -61.00 150.00  104
 37  ω     16.00  61.00   0.50    2.00    --   94.60 -61.00 150.00   90
 38  ω     71.00 183.00   0.50    2.00    --   94.60  61.00-120.00  224
 39  ω     73.00 149.00   0.50    2.00    --   94.60  61.00  90.00  152
 40  ω    100.00 184.00   0.50    2.00    --   94.60  82.00 120.00  168
 41  ω    150.00 184.00   0.50    2.00    --   94.60  82.00  60.00   68
 42  ω    135.00 184.00   0.50    2.00    --   94.60  70.00-178.17   98
 43  ω    157.00 182.00   0.50    2.00    --   94.60  61.00 150.00   50
 44  ω     73.00 141.00   0.50    2.00    --   94.60  61.00 150.00  136
 45  ω     26.00 109.00   0.50    2.00    --   94.60 -82.00 150.00  166
 46  ω    149.00 175.00   0.50    2.00    --   94.60  75.00-105.73   52
 47  ω     71.00 140.00   0.50    2.00    --   94.60  75.00-105.73  138
 48  ω     45.00 120.00   0.50    2.00    --   94.60 -82.00 -30.00  150
 49  ω     72.00 111.00   0.50    2.00    --   94.60  70.00-178.17   78
 50  ω     63.00 111.00   0.50    2.00    --   94.60 -61.00   0.00   96
 51  ω    141.00 184.00   0.50    2.00    --   94.60  68.00  13.99   86
 52  ω      6.00  31.00   0.50    2.00    --   94.60 -61.00   0.00   50
 53  ω    133.00 178.00   0.50    2.00    --   94.60  61.00   0.00   90
 54  ω     96.00 126.00   0.50    2.00    --   94.60 -82.00-180.00   60
 55  ω     70.00 130.00   0.50    2.00    --   94.60  68.00  13.99  120
;
_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      -0.1184065000
_diffrn_orient_matrix_UB_12      0.0059619000
_diffrn_orient_matrix_UB_13      -0.1158697000
_diffrn_orient_matrix_UB_21      -0.0823439000
_diffrn_orient_matrix_UB_22      -0.1402863000
_diffrn_orient_matrix_UB_23      -0.0405056000
_diffrn_orient_matrix_UB_31      -0.2835291000
_diffrn_orient_matrix_UB_32      0.0186983000
_diffrn_orient_matrix_UB_33      0.0311372000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0703
_diffrn_reflns_av_unetI/netI     0.0409
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            12040
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        64.976
_diffrn_reflns_theta_max         64.976
_diffrn_reflns_theta_min         3.633
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.835
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.28443
_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    1.349
_exptl_crystal_description       needle
_exptl_crystal_F_000             300
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.298
_refine_diff_density_min         -0.313
_refine_diff_density_rms         0.065
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     201
_refine_ls_number_reflns         2344
_refine_ls_number_restraints     8
_refine_ls_restrained_S_all      1.053
_refine_ls_R_factor_all          0.0754
_refine_ls_R_factor_gt           0.0652
_refine_ls_shift/su_max          0.008
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.1209P)²+0.2766P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1827
_refine_ls_wR_factor_ref         0.1918
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1917
_reflns_number_total             2344
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d2nj03531f2.cif
_cod_data_source_block           20200729_lfl5-23-2
_cod_depositor_comments          'Adding full bibliography for 7061776.cif.'
_cod_original_cell_volume        690.06(9)
_cod_database_code               7061776
_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   0.975
_shelx_estimated_absorpt_t_min   0.680
_reflns_odcompleteness_completeness 99.76
_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, All C(H,H,H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2. Restrained distances
 C8-C9 \\sim C8-C9A
 with sigma of 0.02
 C9-C10 \\sim C9A-C10A
 with sigma of 0.02
 C9-O3 \\sim C9A-O3A
 with sigma of 0.02
 C10-O4 \\sim C10A-O4A
 with sigma of 0.02
 C8-C10 \\sim C8-C10A
 with sigma of 0.04
 C8-O3 \\sim C8-O3A
 with sigma of 0.04
 C9-O4 \\sim C9A-O4A
 with sigma of 0.04
 C10-O3 \\sim C10A-O3A
 with sigma of 0.04
3. Uiso/Uaniso restraints and constraints
Uanis(C9) = Uanis(C9A)
Uanis(C10) = Uanis(C10A)
Uanis(O3) = Uanis(O4A)
Uanis(O4) = Uanis(O3A)
4. Others
 Sof(H8BC)=Sof(H8BD)=Sof(C9A)=Sof(H9A)=Sof(C10A)=Sof(H10C)=Sof(H10D)=Sof(O3A)=
 Sof(H3A)=Sof(O4A)=Sof(H4A)=1-FVAR(1)
 Sof(H8AA)=Sof(H8AB)=Sof(C9)=Sof(H9)=Sof(C10)=Sof(H10A)=Sof(H10B)=Sof(O3)=
 Sof(H3)=Sof(O4)=Sof(H4)=FVAR(1)
5.a Ternary CH refined with riding coordinates:
 C9(H9), C9A(H9A)
5.b Secondary CH2 refined with riding coordinates:
 C8(H8AA,H8AB), C8(H8BC,H8BD), C11(H11A,H11B), C10(H10A,H10B), C10A(H10C,H10D)
5.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C5(H5), C6(H6), C12(H12)
5.d Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C), C15(H15A,H15B,H15C)
5.e Idealised tetrahedral OH refined as rotating group:
 O5(H5A), O3(H3), O4(H4), O3A(H3A), O4A(H4A)
;
_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 2.579
_oxdiff_exptl_absorpt_empirical_full_min 0.461
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -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 0.7989(5) 0.2016(2) 0.88188(19) 0.0358(6) Uani 1 1 d . . . . .
C2 C 0.5945(5) 0.2012(2) 0.79298(19) 0.0347(6) Uani 1 1 d . . . . .
H2 H 0.5997 0.2674 0.7656 0.042 Uiso 1 1 calc R . . . .
C3 C 0.3850(5) 0.1051(2) 0.74463(19) 0.0344(6) Uani 1 1 d . . . . .
C4 C 0.3835(6) 0.0058(2) 0.7875(2) 0.0379(6) Uani 1 1 d . . . . .
C5 C 0.5845(6) 0.0054(2) 0.8766(2) 0.0410(6) Uani 1 1 d . . . . .
H5 H 0.5803 -0.0608 0.9042 0.049 Uiso 1 1 calc R . . . .
C6 C 0.7905(6) 0.1034(2) 0.9242(2) 0.0394(6) Uani 1 1 d . . . . .
H6 H 0.9234 0.1037 0.9845 0.047 Uiso 1 1 calc R . . . .
C7 C 1.0184(5) 0.3067(2) 0.92883(19) 0.0367(6) Uani 1 1 d . . . . .
C8 C 1.3952(6) 0.4066(2) 1.0761(2) 0.0422(6) Uani 1 1 d D . . . .
H8AA H 1.3514 0.4769 1.0520 0.051 Uiso 0.856(4) 1 calc R . P A 1
H8AB H 1.5683 0.3832 1.0563 0.051 Uiso 0.856(4) 1 calc R . P A 1
H8BC H 1.3165 0.4837 1.0884 0.051 Uiso 0.144(4) 1 calc R . P A 2
H8BD H 1.5249 0.4061 1.0282 0.051 Uiso 0.144(4) 1 calc R . P A 2
C11 C 0.1600(6) 0.1001(2) 0.6472(2) 0.0388(6) Uani 1 1 d . . . . .
H11A H 0.1908 0.0373 0.5832 0.047 Uiso 1 1 calc R . . . .
H11B H -0.0159 0.0745 0.6618 0.047 Uiso 1 1 calc R . . . .
C12 C 0.1382(6) 0.2182(2) 0.6193(2) 0.0393(6) Uani 1 1 d . . . . .
H12 H 0.0432 0.2754 0.6608 0.047 Uiso 1 1 calc R . . . .
C13 C 0.2393(5) 0.2497(2) 0.5420(2) 0.0384(6) Uani 1 1 d . . . . .
C14 C 0.4111(6) 0.1733(3) 0.4701(2) 0.0457(7) Uani 1 1 d . . . . .
H14A H 0.4472 0.1024 0.4927 0.069 Uiso 1 1 calc GR . . . .
H14B H 0.5826 0.2214 0.4766 0.069 Uiso 1 1 calc GR . . . .
H14C H 0.3130 0.1475 0.3950 0.069 Uiso 1 1 calc GR . . . .
C15 C 0.1827(7) 0.3684(2) 0.5193(2) 0.0501(7) Uani 1 1 d . . . . .
H15A H 0.0842 0.3507 0.4448 0.075 Uiso 1 1 calc GR . . . .
H15B H 0.3544 0.4183 0.5297 0.075 Uiso 1 1 calc GR . . . .
H15C H 0.0736 0.4117 0.5687 0.075 Uiso 1 1 calc GR . . . .
O1 O 1.0570(4) 0.38764(15) 0.88835(13) 0.0407(5) Uani 1 1 d . . . . .
O2 O 1.1770(4) 0.30488(15) 1.02331(14) 0.0427(5) Uani 1 1 d . . . . .
O5 O 0.1777(4) -0.08807(16) 0.73714(15) 0.0444(5) Uani 1 1 d . . . . .
H5A H 0.2126 -0.1475 0.7577 0.067 Uiso 1 1 calc GR . . . .
C9 C 1.4216(7) 0.4400(3) 1.2002(2) 0.0432(8) Uani 0.856(4) 1 d D . P A 1
H9 H 1.5667 0.5097 1.2351 0.052 Uiso 0.856(4) 1 calc R . P A 1
C10 C 1.5010(7) 0.3353(3) 1.2431(3) 0.0468(9) Uani 0.856(4) 1 d D . P A 1
H10A H 1.5387 0.3638 1.3228 0.056 Uiso 0.856(4) 1 calc R . P A 1
H10B H 1.3481 0.2698 1.2180 0.056 Uiso 0.856(4) 1 calc R . P A 1
O3 O 1.1756(7) 0.4742(3) 1.2363(3) 0.0434(7) Uani 0.856(4) 1 d D . P A 1
H3 H 1.1051 0.5189 1.2030 0.065 Uiso 0.856(4) 1 calc GR . P A 1
O4 O 1.7408(9) 0.2882(4) 1.2060(3) 0.0494(8) Uani 0.856(4) 1 d D . P A 1
H4 H 1.8738 0.3417 1.2318 0.074 Uiso 0.856(4) 1 calc GR . P A 1
C9A C 1.548(3) 0.3971(16) 1.1863(12) 0.0432(8) Uani 0.144(4) 1 d D . P A 2
H9A H 1.6631 0.4754 1.2267 0.052 Uiso 0.144(4) 1 calc R . P A 2
C10A C 1.332(4) 0.3786(16) 1.2510(14) 0.0468(9) Uani 0.144(4) 1 d D . P A 2
H10C H 1.2337 0.2965 1.2158 0.056 Uiso 0.144(4) 1 calc R . P A 2
H10D H 1.4263 0.3817 1.3238 0.056 Uiso 0.144(4) 1 calc R . P A 2
O3A O 1.716(6) 0.302(3) 1.180(2) 0.0494(8) Uani 0.144(4) 1 d D . P A 2
H3A H 1.8735 0.3272 1.1786 0.074 Uiso 0.144(4) 1 calc GR . P A 2
O4A O 1.133(5) 0.463(2) 1.2630(18) 0.0434(7) Uani 0.144(4) 1 d D . P A 2
H4A H 0.9933 0.4341 1.2154 0.065 Uiso 0.144(4) 1 calc GR . P A 2
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
C2 C1 C7 118.9(2) . . ?
C6 C1 C2 119.4(2) . . ?
C6 C1 C7 121.7(2) . . ?
C1 C2 H2 119.1 . . ?
C3 C2 C1 121.8(2) . . ?
C3 C2 H2 119.1 . . ?
C2 C3 C4 117.8(2) . . ?
C2 C3 C11 123.6(2) . . ?
C4 C3 C11 118.5(2) . . ?
C5 C4 C3 121.0(2) . . ?
O5 C4 C3 116.5(2) . . ?
O5 C4 C5 122.5(2) . . ?
C4 C5 H5 120.0 . . ?
C6 C5 C4 119.9(2) . . ?
C6 C5 H5 120.0 . . ?
C1 C6 H6 120.0 . . ?
C5 C6 C1 120.0(2) . . ?
C5 C6 H6 120.0 . . ?
O1 C7 C1 125.0(2) . . ?
O1 C7 O2 122.2(2) . . ?
O2 C7 C1 112.8(2) . . ?
H8AA C8 H8AB 108.4 . . ?
H8BC C8 H8BD 108.1 . . ?
O2 C8 H8AA 110.0 . . ?
O2 C8 H8AB 110.0 . . ?
O2 C8 H8BC 109.5 . . ?
O2 C8 H8BD 109.5 . . ?
O2 C8 C9 108.6(2) . . ?
O2 C8 C9A 110.8(7) . . ?
C9 C8 H8AA 110.0 . . ?
C9 C8 H8AB 110.0 . . ?
C9A C8 H8BC 109.5 . . ?
C9A C8 H8BD 109.5 . . ?
C3 C11 H11A 108.3 . . ?
C3 C11 H11B 108.3 . . ?
H11A C11 H11B 107.4 . . ?
C12 C11 C3 116.0(2) . . ?
C12 C11 H11A 108.3 . . ?
C12 C11 H11B 108.3 . . ?
C11 C12 H12 116.4 . . ?
C13 C12 C11 127.3(2) . . ?
C13 C12 H12 116.4 . . ?
C12 C13 C14 124.6(2) . . ?
C12 C13 C15 120.7(2) . . ?
C14 C13 C15 114.6(2) . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C13 C15 H15A 109.5 . . ?
C13 C15 H15B 109.5 . . ?
C13 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C7 O2 C8 116.3(2) . . ?
C4 O5 H5A 109.5 . . ?
C8 C9 H9 108.1 . . ?
C10 C9 C8 112.3(3) . . ?
C10 C9 H9 108.1 . . ?
O3 C9 C8 113.7(3) . . ?
O3 C9 H9 108.1 . . ?
O3 C9 C10 106.3(3) . . ?
C9 C10 H10A 109.4 . . ?
C9 C10 H10B 109.4 . . ?
H10A C10 H10B 108.0 . . ?
O4 C10 C9 111.2(3) . . ?
O4 C10 H10A 109.4 . . ?
O4 C10 H10B 109.4 . . ?
C9 O3 H3 109.5 . . ?
C10 O4 H4 109.5 . . ?
C8 C9A H9A 108.3 . . ?
C10A C9A C8 107.4(12) . . ?
C10A C9A H9A 108.3 . . ?
O3A C9A C8 116.1(15) . . ?
O3A C9A H9A 108.3 . . ?
O3A C9A C10A 108.2(17) . . ?
C9A C10A H10C 108.0 . . ?
C9A C10A H10D 108.0 . . ?
H10C C10A H10D 107.3 . . ?
O4A C10A C9A 117.1(15) . . ?
O4A C10A H10C 108.0 . . ?
O4A C10A H10D 108.0 . . ?
C9A O3A H3A 109.5 . . ?
C10A O4A H4A 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 C2 1.395(4) . ?
C1 C6 1.392(4) . ?
C1 C7 1.475(3) . ?
C2 H2 0.9300 . ?
C2 C3 1.380(3) . ?
C3 C4 1.407(4) . ?
C3 C11 1.518(3) . ?
C4 C5 1.390(4) . ?
C4 O5 1.356(3) . ?
C5 H5 0.9300 . ?
C5 C6 1.382(4) . ?
C6 H6 0.9300 . ?
C7 O1 1.214(3) . ?
C7 O2 1.344(3) . ?
C8 H8AA 0.9700 . ?
C8 H8AB 0.9700 . ?
C8 H8BC 0.9700 . ?
C8 H8BD 0.9700 . ?
C8 O2 1.452(3) . ?
C8 C9 1.524(4) . ?
C8 C9A 1.536(14) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C11 C12 1.507(4) . ?
C12 H12 0.9300 . ?
C12 C13 1.325(4) . ?
C13 C14 1.504(4) . ?
C13 C15 1.509(4) . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
O5 H5A 0.8200 . ?
C9 H9 0.9800 . ?
C9 C10 1.512(4) . ?
C9 O3 1.420(5) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C10 O4 1.438(5) . ?
O3 H3 0.8200 . ?
O4 H4 0.8200 . ?
C9A H9A 0.9800 . ?
C9A C10A 1.514(16) . ?
C9A O3A 1.411(18) . ?
C10A H10C 0.9700 . ?
C10A H10D 0.9700 . ?
C10A O4A 1.421(17) . ?
O3A H3A 0.8200 . ?
O4A H4A 0.8200 . ?
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
O5 H5A O4 0.82 1.83 2.644(4) 174.3 2_757
O3 H3 O1 0.82 1.93 2.748(3) 174.4 2_767
O4 H4 O3 0.82 2.04 2.822(6) 158.4 1_655
O3A H3A O4A 0.82 1.88 2.53(4) 135.7 1_655
O4A H4A O3A 0.82 1.87 2.53(4) 136.7 1_455
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
C1 C2 C3 C4 -0.3(4) . . . . ?
C1 C2 C3 C11 -179.4(2) . . . . ?
C1 C7 O2 C8 -178.9(2) . . . . ?
C2 C1 C6 C5 1.5(4) . . . . ?
C2 C1 C7 O1 -9.4(4) . . . . ?
C2 C1 C7 O2 170.7(2) . . . . ?
C2 C3 C4 C5 0.9(4) . . . . ?
C2 C3 C4 O5 -179.0(2) . . . . ?
C2 C3 C11 C12 -12.6(4) . . . . ?
C3 C4 C5 C6 -0.2(4) . . . . ?
C3 C11 C12 C13 98.7(3) . . . . ?
C4 C3 C11 C12 168.3(2) . . . . ?
C4 C5 C6 C1 -0.9(4) . . . . ?
C6 C1 C2 C3 -0.8(4) . . . . ?
C6 C1 C7 O1 170.8(2) . . . . ?
C6 C1 C7 O2 -9.1(3) . . . . ?
C7 C1 C2 C3 179.4(2) . . . . ?
C7 C1 C6 C5 -178.8(2) . . . . ?
C8 C9 C10 O4 51.7(4) . . . . ?
C8 C9A C10A O4A -52(2) . . . . ?
C11 C3 C4 C5 180.0(2) . . . . ?
C11 C3 C4 O5 0.2(3) . . . . ?
C11 C12 C13 C14 -3.3(4) . . . . ?
C11 C12 C13 C15 175.8(2) . . . . ?
O1 C7 O2 C8 1.2(4) . . . . ?
O2 C8 C9 C10 61.9(3) . . . . ?
O2 C8 C9 O3 -58.9(3) . . . . ?
O2 C8 C9A C10A -50.6(13) . . . . ?
O2 C8 C9A O3A 70.6(19) . . . . ?
O5 C4 C5 C6 179.6(2) . . . . ?
C9 C8 O2 C7 143.0(2) . . . . ?
O3 C9 C10 O4 176.7(3) . . . . ?
C9A C8 O2 C7 176.5(7) . . . . ?
O3A C9A C10A O4A -178(2) . . . . ?
