data_esr416a
_audit_creation_date              2016-04-12
_audit_creation_method
;
Olex2 1.2-alpha
(compiled 2016.02.24 svn.r3266 for OlexSys, GUI svn.r5155)
;
_shelxl_version_number            2014/6
_publ_contact_author_address      ?
_publ_contact_author_email        ?
_publ_contact_author_name         ''
_publ_contact_author_phone        ?
_publ_section_references
;
Dolomanov, O.V., Bourhis, L.J., Gildea, R.J, Howard, J.A.K. & Puschmann, H.
 (2009), J. Appl. Cryst. 42, 339-341.

Sheldrick, G.M. (2008). Acta Cryst. A64, 112-122.
;
_chemical_name_common             ?
_chemical_name_systematic         ?
_chemical_formula_moiety          'C22 H30 O8'
_chemical_formula_sum             'C22 H30 O8'
_chemical_formula_weight          422.46
_chemical_absolute_configuration  ad
_chemical_melting_point           ?
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'

_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.
;
_space_group_crystal_system       'monoclinic'
_space_group_IT_number            4
_space_group_name_H-M_alt         'P 1 21 1'
_space_group_name_Hall            'P 2yb'
loop_
  _space_group_symop_operation_xyz
 'x, y, z'
 '-x, y+1/2, -z'

_cell_length_a                    6.12890(10)
_cell_length_b                    9.1873(2)
_cell_length_c                    18.5609(3)
_cell_angle_alpha                 90
_cell_angle_beta                  97.5180(10)
_cell_angle_gamma                 90
_cell_volume                      1036.14(3)
_cell_formula_units_Z             2
_cell_measurement_reflns_used     4551
_cell_measurement_temperature     173(2)
_cell_measurement_theta_max       71.86
_cell_measurement_theta_min       2.40
_shelx_estimated_absorpt_T_max    0.973
_shelx_estimated_absorpt_T_min    0.803
_exptl_absorpt_coefficient_mu     0.855
_exptl_absorpt_correction_T_max   1.0000
_exptl_absorpt_correction_T_min   0.8481
_exptl_absorpt_correction_type    multi-scan
_exptl_absorpt_process_details
'SADABS-2012/1 (Bruker,2012) was used for absorption correction. wR2(int) was 0.0624 before and 0.0480 after correction. The Ratio of minimum to maximum transmission is 0.8481. The λ/2 correction factor is 0.0015.'
_exptl_absorpt_special_details    ?
_exptl_crystal_colour             colourless
_exptl_crystal_colour_primary     colourless
_exptl_crystal_density_diffrn     1.354
_exptl_crystal_density_meas       ?
_exptl_crystal_density_method     ?
_exptl_crystal_description        'plate'
_exptl_crystal_F_000              452
_exptl_crystal_recrystallization_method 'used as received'
_exptl_crystal_size_max           0.268
_exptl_crystal_size_mid           0.172
_exptl_crystal_size_min           0.032
_exptl_transmission_factor_max    ?
_exptl_transmission_factor_min    ?
_diffrn_reflns_av_R_equivalents   0.0335
_diffrn_reflns_av_unetI/netI      0.0396
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_limit_h_max        7
_diffrn_reflns_limit_h_min        -7
_diffrn_reflns_limit_k_max        11
_diffrn_reflns_limit_k_min        -11
_diffrn_reflns_limit_l_max        22
_diffrn_reflns_limit_l_min        -22
_diffrn_reflns_number             9574
_diffrn_reflns_point_group_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.972
_diffrn_reflns_theta_full         67.679
_diffrn_reflns_theta_max          72.017
_diffrn_reflns_theta_min          2.401
_diffrn_ambient_temperature       173(2)
_diffrn_detector_area_resol_mean  8.36
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device_type   'Bruker APEX-II CCD'
_diffrn_measurement_method        'ω and φ'
_diffrn_radiation_monochromator   graphite
_diffrn_radiation_type            CuK\a
_diffrn_radiation_wavelength      1.54178
_diffrn_source                    'sealed tube'
_diffrn_standards_number          0
_reflns_Friedel_coverage          0.842
_reflns_Friedel_fraction_full     0.982
_reflns_Friedel_fraction_max      0.952
_reflns_number_gt                 3531
_reflns_number_total              3976
_reflns_special_details
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression      'I > 2σ(I)'
_computing_cell_refinement        'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection        'COSMO (BRUKER, V1.61, 2009)'
_computing_data_reduction         'SAINT v8.34A (Bruker, 2013)'
_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)'
_refine_diff_density_max          0.221
_refine_diff_density_min          -0.209
_refine_diff_density_rms          0.041
_refine_ls_abs_structure_details
;
 Flack x determined using 1468 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack    -0.10(12)
_refine_ls_extinction_coef        .
_refine_ls_extinction_method      none
_refine_ls_goodness_of_fit_ref    1.055
_refine_ls_hydrogen_treatment     mixed
_refine_ls_matrix_type            full
_refine_ls_number_parameters      278
_refine_ls_number_reflns          3976
_refine_ls_number_restraints      1
_refine_ls_R_factor_all           0.0474
_refine_ls_R_factor_gt            0.0403
_refine_ls_restrained_S_all       1.055
_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)+(0.0475P)²+0.1303P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme       calc
_refine_ls_wR_factor_gt           0.0939
_refine_ls_wR_factor_ref          0.0979
_refine_special_details
;
The structure was refined by Least Squares using version 2014/6 
of XL (Sheldrick, 2008) incorporated in Olex2 (Dolomanov et al., 2009). 
All non-hydrogen atoms were refined anisotropically. 
Hydrogen atom positions were calculated geometrically and refined using the riding model.
;
_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.a Ternary CH refined with riding coordinates:
 C1(H1), C4(H4A), C5(H5A), C6(H6), C7(H7), C8(H8), C9(H9), C10(H10)
2.b Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C3(H3A,H3B), C11(H11A,H11B), C12(H12A,H12B), C13(H13A,H13B),
 C20(H20A,H20B)
2.c Aromatic/amide H refined with riding coordinates:
 C15(H15), C16(H16), C17(H17), C18(H18), C19(H19)
2.d Idealised Me refined as rotating group:
 C22(H22A,H22B,H22C)
;
_atom_sites_solution_hydrogens    mixed
_atom_sites_solution_primary      direct
_atom_sites_solution_secondary    ?
_atom_sites_special_details
;
The structure was solved using Direct Methods (ShelXS). RE = 0.2, Nqual =  -1, Ralpha = 0.047
;
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 0.1616(3) 0.1570(2) 0.20607(11) 0.0291(5) Uani 1 1 d . . . . .
 O2 O -0.2115(3) 0.1646(2) 0.34650(11) 0.0278(5) Uani 1 1 d . . . . .
 O3 O 0.2822(3) 0.2920(2) 0.45868(11) 0.0297(5) Uani 1 1 d . . . . .
 O4 O 0.3518(3) 0.1030(2) 0.34846(11) 0.0257(4) Uani 1 1 d . . . . .
 H4 H 0.476(6) 0.118(4) 0.354(2) 0.039 Uiso 1 1 d R . . . .
 O5 O 0.1005(3) -0.0237(2) 0.43844(12) 0.0269(4) Uani 1 1 d . . . . .
 H5 H 0.201(6) 0.004(4) 0.415(2) 0.040 Uiso 1 1 d R . . . .
 O6 O 0.6730(4) 0.1383(2) 0.65328(12) 0.0355(5) Uani 1 1 d . . . . .
 O7 O 0.4360(4) 0.1451(3) 0.02744(13) 0.0409(6) Uani 1 1 d . . . . .
 O8 O 0.1691(5) 0.3077(3) 0.03268(17) 0.0620(9) Uani 1 1 d . . . . .
 C1 C 0.0039(5) 0.1258(4) 0.14368(16) 0.0297(6) Uani 1 1 d . . . . .
 H1 H -0.0737 0.2177 0.1266 0.036 Uiso 1 1 calc R . . . .
 C2 C -0.1645(5) 0.0149(4) 0.16213(17) 0.0322(7) Uani 1 1 d . . . . .
 H2A H -0.0903 -0.0788 0.1755 0.039 Uiso 1 1 calc R . . . .
 H2B H -0.2752 -0.0018 0.1191 0.039 Uiso 1 1 calc R . . . .
 C3 C -0.2793(5) 0.0695(4) 0.22543(17) 0.0304(7) Uani 1 1 d . . . . .
 H3A H -0.3653 0.1584 0.2109 0.037 Uiso 1 1 calc R . . . .
 H3B H -0.3814 -0.0058 0.2395 0.037 Uiso 1 1 calc R . . . .
 C4 C -0.1043(4) 0.1027(3) 0.28887(16) 0.0251(6) Uani 1 1 d . . . . .
 H4A H -0.0273 0.0107 0.3062 0.030 Uiso 1 1 calc R . . . .
 C5 C 0.0630(4) 0.2116(3) 0.26613(16) 0.0246(6) Uani 1 1 d . . . . .
 H5A H -0.0130 0.3057 0.2521 0.030 Uiso 1 1 calc R . . . .
 C6 C 0.2433(4) 0.2378(3) 0.32919(16) 0.0239(6) Uani 1 1 d . . . . .
 H6 H 0.3517 0.3097 0.3145 0.029 Uiso 1 1 calc R . . . .
 C7 C 0.1343(5) 0.2996(3) 0.39301(16) 0.0248(6) Uani 1 1 d . . . . .
 H7 H 0.0944 0.4038 0.3827 0.030 Uiso 1 1 calc R . . . .
 C8 C -0.0730(4) 0.2164(3) 0.40896(16) 0.0253(6) Uani 1 1 d . . . . .
 H8 H -0.1630 0.2870 0.4336 0.030 Uiso 1 1 calc R . . . .
 C9 C 0.0180(4) 0.1052(3) 0.46684(15) 0.0249(6) Uani 1 1 d . . . . .
 H9 H -0.0991 0.0796 0.4975 0.030 Uiso 1 1 calc R . . . .
 C10 C 0.1921(5) 0.1979(3) 0.51080(15) 0.0256(6) Uani 1 1 d . . . . .
 H10 H 0.1186 0.2604 0.5446 0.031 Uiso 1 1 calc R . . . .
 C11 C 0.3785(5) 0.1164(3) 0.55467(16) 0.0274(6) Uani 1 1 d . . . . .
 H11A H 0.3173 0.0432 0.5856 0.033 Uiso 1 1 calc R . . . .
 H11B H 0.4650 0.0642 0.5213 0.033 Uiso 1 1 calc R . . . .
 C12 C 0.5275(5) 0.2186(4) 0.60190(17) 0.0347(7) Uani 1 1 d . . . . .
 H12A H 0.6139 0.2778 0.5712 0.042 Uiso 1 1 calc R . . . .
 H12B H 0.4378 0.2855 0.6278 0.042 Uiso 1 1 calc R . . . .
 C13 C 0.7832(9) 0.2305(5) 0.7070(3) 0.0756(17) Uani 1 1 d . . . . .
 H13A H 0.6757 0.2716 0.7370 0.091 Uiso 1 1 calc R . . . .
 H13B H 0.8516 0.3122 0.6834 0.091 Uiso 1 1 calc R . . . .
 C14 C 0.9563(6) 0.1490(4) 0.75464(18) 0.0371(7) Uani 1 1 d . . . . .
 C15 C 1.1527(7) 0.1163(5) 0.7300(2) 0.0542(11) Uani 1 1 d . . . . .
 H15 H 1.1728 0.1448 0.6821 0.065 Uiso 1 1 calc R . . . .
 C16 C 1.3180(7) 0.0458(6) 0.7708(3) 0.0662(14) Uani 1 1 d . . . . .
 H16 H 1.4508 0.0250 0.7515 0.079 Uiso 1 1 calc R . . . .
 C17 C 1.2938(7) 0.0048(5) 0.8392(3) 0.0563(11) Uani 1 1 d . . . . .
 H17 H 1.4108 -0.0437 0.8682 0.068 Uiso 1 1 calc R . . . .
 C18 C 1.1010(8) 0.0329(5) 0.86713(19) 0.0515(11) Uani 1 1 d . . . . .
 H18 H 1.0843 0.0031 0.9151 0.062 Uiso 1 1 calc R . . . .
 C19 C 0.9288(6) 0.1059(4) 0.82431(19) 0.0421(9) Uani 1 1 d . . . . .
 H19 H 0.7948 0.1254 0.8430 0.051 Uiso 1 1 calc R . . . .
 C20 C 0.1363(6) 0.0716(4) 0.08555(18) 0.0360(7) Uani 1 1 d . . . . .
 H20A H 0.2511 0.0040 0.1082 0.043 Uiso 1 1 calc R . . . .
 H20B H 0.0376 0.0158 0.0491 0.043 Uiso 1 1 calc R . . . .
 C21 C 0.2455(6) 0.1902(4) 0.04713(16) 0.0358(8) Uani 1 1 d . . . . .
 C22 C 0.5455(6) 0.2459(5) -0.0158(2) 0.0515(10) Uani 1 1 d . . . . .
 H22A H 0.4647 0.2513 -0.0649 0.077 Uiso 1 1 calc GR . . . .
 H22B H 0.6959 0.2121 -0.0185 0.077 Uiso 1 1 calc GR . . . .
 H22C H 0.5501 0.3425 0.0067 0.077 Uiso 1 1 calc GR . . . .


_geom_special_details
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
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 C1 1.437(4) . ?
 O1 C5 1.427(3) . ?
 O2 C4 1.443(3) . ?
 O2 C8 1.426(3) . ?
 O3 C7 1.422(4) . ?
 O3 C10 1.458(3) . ?
 O4 H4 0.76(4) . ?
 O4 C6 1.429(3) . ?
 O5 H5 0.83(4) . ?
 O5 C9 1.416(4) . ?
 O6 C12 1.423(4) . ?
 O6 C13 1.412(4) . ?
 O7 C21 1.334(4) . ?
 O7 C22 1.447(5) . ?
 O8 C21 1.193(4) . ?
 C1 H1 1.0000 . ?
 C1 C2 1.521(4) . ?
 C1 C20 1.516(4) . ?
 C2 H2A 0.9900 . ?
 C2 H2B 0.9900 . ?
 C2 C3 1.531(4) . ?
 C3 H3A 0.9900 . ?
 C3 H3B 0.9900 . ?
 C3 C4 1.516(4) . ?
 C4 H4A 1.0000 . ?
 C4 C5 1.531(4) . ?
 C5 H5A 1.0000 . ?
 C5 C6 1.520(4) . ?
 C6 H6 1.0000 . ?
 C6 C7 1.542(4) . ?
 C7 H7 1.0000 . ?
 C7 C8 1.544(4) . ?
 C8 H8 1.0000 . ?
 C8 C9 1.534(4) . ?
 C9 H9 1.0000 . ?
 C9 C10 1.518(4) . ?
 C10 H10 1.0000 . ?
 C10 C11 1.512(4) . ?
 C11 H11A 0.9900 . ?
 C11 H11B 0.9900 . ?
 C11 C12 1.508(4) . ?
 C12 H12A 0.9900 . ?
 C12 H12B 0.9900 . ?
 C13 H13A 0.9900 . ?
 C13 H13B 0.9900 . ?
 C13 C14 1.490(5) . ?
 C14 C15 1.375(6) . ?
 C14 C19 1.384(5) . ?
 C15 H15 0.9500 . ?
 C15 C16 1.349(7) . ?
 C16 H16 0.9500 . ?
 C16 C17 1.350(7) . ?
 C17 H17 0.9500 . ?
 C17 C18 1.376(6) . ?
 C18 H18 0.9500 . ?
 C18 C19 1.405(6) . ?
 C19 H19 0.9500 . ?
 C20 H20A 0.9900 . ?
 C20 H20B 0.9900 . ?
 C20 C21 1.506(5) . ?
 C22 H22A 0.9800 . ?
 C22 H22B 0.9800 . ?
 C22 H22C 0.9800 . ?

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
 C5 O1 C1 113.0(2) . . ?
 C8 O2 C4 117.0(2) . . ?
 C7 O3 C10 110.1(2) . . ?
 C6 O4 H4 107(3) . . ?
 C9 O5 H5 105(3) . . ?
 C13 O6 C12 111.2(3) . . ?
 C21 O7 C22 116.1(3) . . ?
 O1 C1 H1 109.2 . . ?
 O1 C1 C2 110.9(2) . . ?
 O1 C1 C20 105.8(2) . . ?
 C2 C1 H1 109.2 . . ?
 C20 C1 H1 109.2 . . ?
 C20 C1 C2 112.5(3) . . ?
 C1 C2 H2A 109.6 . . ?
 C1 C2 H2B 109.6 . . ?
 C1 C2 C3 110.3(3) . . ?
 H2A C2 H2B 108.1 . . ?
 C3 C2 H2A 109.6 . . ?
 C3 C2 H2B 109.6 . . ?
 C2 C3 H3A 110.1 . . ?
 C2 C3 H3B 110.1 . . ?
 H3A C3 H3B 108.4 . . ?
 C4 C3 C2 108.2(2) . . ?
 C4 C3 H3A 110.1 . . ?
 C4 C3 H3B 110.1 . . ?
 O2 C4 C3 108.1(2) . . ?
 O2 C4 H4A 109.6 . . ?
 O2 C4 C5 109.5(2) . . ?
 C3 C4 H4A 109.6 . . ?
 C3 C4 C5 110.4(2) . . ?
 C5 C4 H4A 109.6 . . ?
 O1 C5 C4 110.7(2) . . ?
 O1 C5 H5A 109.3 . . ?
 O1 C5 C6 108.5(2) . . ?
 C4 C5 H5A 109.3 . . ?
 C6 C5 C4 109.7(2) . . ?
 C6 C5 H5A 109.3 . . ?
 O4 C6 C5 108.9(2) . . ?
 O4 C6 H6 109.7 . . ?
 O4 C6 C7 111.2(2) . . ?
 C5 C6 H6 109.7 . . ?
 C5 C6 C7 107.8(2) . . ?
 C7 C6 H6 109.7 . . ?
 O3 C7 C6 110.4(2) . . ?
 O3 C7 H7 108.9 . . ?
 O3 C7 C8 105.0(2) . . ?
 C6 C7 H7 108.9 . . ?
 C6 C7 C8 114.5(2) . . ?
 C8 C7 H7 108.9 . . ?
 O2 C8 C7 115.3(2) . . ?
 O2 C8 H8 106.5 . . ?
 O2 C8 C9 118.1(3) . . ?
 C7 C8 H8 106.5 . . ?
 C9 C8 C7 103.4(2) . . ?
 C9 C8 H8 106.5 . . ?
 O5 C9 C8 114.3(2) . . ?
 O5 C9 H9 109.4 . . ?
 O5 C9 C10 114.2(2) . . ?
 C8 C9 H9 109.4 . . ?
 C10 C9 C8 99.7(2) . . ?
 C10 C9 H9 109.4 . . ?
 O3 C10 C9 106.1(2) . . ?
 O3 C10 H10 108.5 . . ?
 O3 C10 C11 109.0(2) . . ?
 C9 C10 H10 108.5 . . ?
 C11 C10 C9 116.1(2) . . ?
 C11 C10 H10 108.5 . . ?
 C10 C11 H11A 109.4 . . ?
 C10 C11 H11B 109.4 . . ?
 H11A C11 H11B 108.0 . . ?
 C12 C11 C10 111.2(2) . . ?
 C12 C11 H11A 109.4 . . ?
 C12 C11 H11B 109.4 . . ?
 O6 C12 C11 110.2(3) . . ?
 O6 C12 H12A 109.6 . . ?
 O6 C12 H12B 109.6 . . ?
 C11 C12 H12A 109.6 . . ?
 C11 C12 H12B 109.6 . . ?
 H12A C12 H12B 108.1 . . ?
 O6 C13 H13A 109.5 . . ?
 O6 C13 H13B 109.5 . . ?
 O6 C13 C14 110.8(3) . . ?
 H13A C13 H13B 108.1 . . ?
 C14 C13 H13A 109.5 . . ?
 C14 C13 H13B 109.5 . . ?
 C15 C14 C13 119.9(4) . . ?
 C15 C14 C19 117.8(4) . . ?
 C19 C14 C13 122.2(4) . . ?
 C14 C15 H15 118.5 . . ?
 C16 C15 C14 122.9(4) . . ?
 C16 C15 H15 118.5 . . ?
 C15 C16 H16 120.2 . . ?
 C15 C16 C17 119.7(4) . . ?
 C17 C16 H16 120.2 . . ?
 C16 C17 H17 119.7 . . ?
 C16 C17 C18 120.5(4) . . ?
 C18 C17 H17 119.7 . . ?
 C17 C18 H18 120.2 . . ?
 C17 C18 C19 119.6(4) . . ?
 C19 C18 H18 120.2 . . ?
 C14 C19 C18 119.4(4) . . ?
 C14 C19 H19 120.3 . . ?
 C18 C19 H19 120.3 . . ?
 C1 C20 H20A 108.7 . . ?
 C1 C20 H20B 108.7 . . ?
 H20A C20 H20B 107.6 . . ?
 C21 C20 C1 114.3(3) . . ?
 C21 C20 H20A 108.7 . . ?
 C21 C20 H20B 108.7 . . ?
 O7 C21 C20 111.3(3) . . ?
 O8 C21 O7 123.4(3) . . ?
 O8 C21 C20 125.2(3) . . ?
 O7 C22 H22A 109.5 . . ?
 O7 C22 H22B 109.5 . . ?
 O7 C22 H22C 109.5 . . ?
 H22A C22 H22B 109.5 . . ?
 H22A C22 H22C 109.5 . . ?
 H22B C22 H22C 109.5 . . ?

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 O2 0.76(4) 1.99(4) 2.740(3) 169(4) 1_655
 O5 H5 O4 0.83(4) 1.88(4) 2.681(3) 161(4) .

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
 O1 C1 C2 C3 56.8(3) . . . . ?
 O1 C1 C20 C21 -78.9(3) . . . . ?
 O1 C5 C6 O4 -60.4(3) . . . . ?
 O1 C5 C6 C7 178.9(2) . . . . ?
 O2 C4 C5 O1 -176.3(2) . . . . ?
 O2 C4 C5 C6 64.0(3) . . . . ?
 O2 C8 C9 O5 44.7(3) . . . . ?
 O2 C8 C9 C10 166.9(2) . . . . ?
 O3 C7 C8 O2 -158.8(2) . . . . ?
 O3 C7 C8 C9 -28.5(3) . . . . ?
 O3 C10 C11 C12 66.3(3) . . . . ?
 O4 C6 C7 O3 46.1(3) . . . . ?
 O4 C6 C7 C8 -72.2(3) . . . . ?
 O5 C9 C10 O3 86.8(3) . . . . ?
 O5 C9 C10 C11 -34.5(3) . . . . ?
 O6 C13 C14 C15 76.8(5) . . . . ?
 O6 C13 C14 C19 -104.2(5) . . . . ?
 C1 O1 C5 C4 58.5(3) . . . . ?
 C1 O1 C5 C6 178.9(2) . . . . ?
 C1 C2 C3 C4 -55.8(3) . . . . ?
 C1 C20 C21 O7 147.5(3) . . . . ?
 C1 C20 C21 O8 -35.7(5) . . . . ?
 C2 C1 C20 C21 159.8(3) . . . . ?
 C2 C3 C4 O2 175.7(2) . . . . ?
 C2 C3 C4 C5 56.0(3) . . . . ?
 C3 C4 C5 O1 -57.5(3) . . . . ?
 C3 C4 C5 C6 -177.2(2) . . . . ?
 C4 O2 C8 C7 41.2(3) . . . . ?
 C4 O2 C8 C9 -81.5(3) . . . . ?
 C4 C5 C6 O4 60.6(3) . . . . ?
 C4 C5 C6 C7 -60.1(3) . . . . ?
 C5 O1 C1 C2 -58.5(3) . . . . ?
 C5 O1 C1 C20 179.2(2) . . . . ?
 C5 C6 C7 O3 165.3(2) . . . . ?
 C5 C6 C7 C8 47.0(3) . . . . ?
 C6 C7 C8 O2 -37.5(3) . . . . ?
 C6 C7 C8 C9 92.8(3) . . . . ?
 C7 O3 C10 C9 19.1(3) . . . . ?
 C7 O3 C10 C11 144.8(2) . . . . ?
 C7 C8 C9 O5 -83.8(3) . . . . ?
 C7 C8 C9 C10 38.3(3) . . . . ?
 C8 O2 C4 C3 -174.3(2) . . . . ?
 C8 O2 C4 C5 -54.0(3) . . . . ?
 C8 C9 C10 O3 -35.5(3) . . . . ?
 C8 C9 C10 C11 -156.7(2) . . . . ?
 C9 C10 C11 C12 -174.0(2) . . . . ?
 C10 O3 C7 C6 -117.8(2) . . . . ?
 C10 O3 C7 C8 6.1(3) . . . . ?
 C10 C11 C12 O6 167.9(2) . . . . ?
 C12 O6 C13 C14 -172.4(4) . . . . ?
 C13 O6 C12 C11 -168.3(4) . . . . ?
 C13 C14 C15 C16 178.5(4) . . . . ?
 C13 C14 C19 C18 -178.2(3) . . . . ?
 C14 C15 C16 C17 -0.3(7) . . . . ?
 C15 C14 C19 C18 0.8(5) . . . . ?
 C15 C16 C17 C18 0.8(7) . . . . ?
 C16 C17 C18 C19 -0.5(6) . . . . ?
 C17 C18 C19 C14 -0.3(6) . . . . ?
 C19 C14 C15 C16 -0.5(6) . . . . ?
 C20 C1 C2 C3 175.1(3) . . . . ?
 C22 O7 C21 O8 -2.2(5) . . . . ?
 C22 O7 C21 C20 174.6(3) . . . . ?

_olex2_diffrn_ambient_temperature_device 'Oxford Cryosystems'
_olex2_exptl_crystal_mounting_method
'The crystal was mounted on a nylon loop with paratone oil'
_olex2_submission_original_sample_id ER-001229919
_olex2_submission_special_instructions 'No special instructions were received'

