data_esr416b
_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 H28 O8'
_chemical_formula_sum             'C22 H28 O8'
_chemical_formula_weight          420.44
_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            5
_space_group_name_H-M_alt         'C 1 2 1'
_space_group_name_Hall            'C 2y'
loop_
  _space_group_symop_operation_xyz
 'x, y, z'
 '-x, y, -z'
 'x+1/2, y+1/2, z'
 '-x+1/2, y+1/2, -z'

_cell_length_a                    33.1345(5)
_cell_length_b                    5.78770(10)
_cell_length_c                    10.7579(2)
_cell_angle_alpha                 90
_cell_angle_beta                  92.1810(10)
_cell_angle_gamma                 90
_cell_volume                      2061.58(6)
_cell_formula_units_Z             4
_cell_measurement_reflns_used     5729
_cell_measurement_temperature     173(2)
_cell_measurement_theta_max       72.02
_cell_measurement_theta_min       4.11
_shelx_estimated_absorpt_T_max    0.943
_shelx_estimated_absorpt_T_min    0.703
_exptl_absorpt_coefficient_mu     0.859
_exptl_absorpt_correction_T_max   0.9738
_exptl_absorpt_correction_T_min   0.8448
_exptl_absorpt_correction_type    multi-scan
_exptl_absorpt_process_details
'SADABS-2012/1 (Bruker,2012) was used for absorption correction. wR2(int) was 0.0674 before and 0.0557 after correction. The Ratio of minimum to maximum transmission is 0.8675. 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     1.355
_exptl_crystal_density_meas       ?
_exptl_crystal_density_method     ?
_exptl_crystal_description        'needle'
_exptl_crystal_F_000              896
_exptl_crystal_recrystallization_method 'used as received'
_exptl_crystal_size_max           0.441
_exptl_crystal_size_mid           0.095
_exptl_crystal_size_min           0.069
_exptl_special_details
;
Data was collected using a BRUKER CCD (charge coupled device) based
diffractometer equipped with an Oxford low-temperature apparatus operating at
173 K.  A suitable crystal was chosen and mounted on a nylon loop using 
Paratone oil.  Data  were measured using omega and phi scans of 1.0° per frame 
for 30 s. The total number of images were based on 
results from the program COSMO where redundancy was expected to be 4 and 
completeness to 0.83Å to 100%. Cell parameters were
retrieved using APEX II software and refined using SAINT on all observed
reflections.Data reduction was performed using the SAINT software which 
corrects for Lp. Scaling and absorption corrections were applied using SADABS6 
multi-scan technique, supplied by George Sheldrick.  The structures are solved 
by the direct method using the SHELXS-97 program and refined by least squares 
method on F2, SHELXL-97, incorporated in OLEX2. 
;
_exptl_transmission_factor_max    ?
_exptl_transmission_factor_min    ?
_diffrn_reflns_av_R_equivalents   0.0391
_diffrn_reflns_av_unetI/netI      0.0363
_diffrn_reflns_Laue_measured_fraction_full 0.977
_diffrn_reflns_Laue_measured_fraction_max 0.969
_diffrn_reflns_limit_h_max        40
_diffrn_reflns_limit_h_min        -40
_diffrn_reflns_limit_k_max        7
_diffrn_reflns_limit_k_min        -7
_diffrn_reflns_limit_l_max        12
_diffrn_reflns_limit_l_min        -11
_diffrn_reflns_number             11841
_diffrn_reflns_point_group_measured_fraction_full 0.967
_diffrn_reflns_point_group_measured_fraction_max 0.951
_diffrn_reflns_theta_full         67.679
_diffrn_reflns_theta_max          72.153
_diffrn_reflns_theta_min          4.112
_diffrn_ambient_temperature       173(2)
_diffrn_detector_area_resol_mean  8.36
_diffrn_measured_fraction_theta_full 0.977
_diffrn_measured_fraction_theta_max 0.969
_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          0.776
_reflns_Friedel_fraction_full     0.953
_reflns_Friedel_fraction_max      0.928
_reflns_number_gt                 3518
_reflns_number_total              3862
_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          0.190
_refine_diff_density_min          -0.161
_refine_diff_density_rms          0.034
_refine_ls_abs_structure_details
;
 Flack x determined using 1431 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack    0.00(10)
_refine_ls_extinction_coef        .
_refine_ls_extinction_method      none
_refine_ls_goodness_of_fit_ref    1.029
_refine_ls_hydrogen_treatment     mixed
_refine_ls_matrix_type            full
_refine_ls_number_parameters      275
_refine_ls_number_reflns          3862
_refine_ls_number_restraints      1
_refine_ls_R_factor_all           0.0416
_refine_ls_R_factor_gt            0.0367
_refine_ls_restrained_S_all       1.028
_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)+(0.0531P)²+0.3171P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme       calc
_refine_ls_wR_factor_gt           0.0909
_refine_ls_wR_factor_ref          0.0945
_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:
 C2(H2), C3(H3), C4(H4), C5(H5A), C6(H6), C7(H7), C10(H10)
2.b Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B), C9(H9A,H9B), 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 = 0.051
;
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 0.64922(5) 0.2464(3) 1.08655(17) 0.0328(4) Uani 1 1 d . . . . .
 O2 O 0.62633(5) 0.5707(3) 0.99037(16) 0.0278(4) Uani 1 1 d . . . . .
 O3 O 0.60011(6) 0.1597(3) 0.78415(18) 0.0374(4) Uani 1 1 d . . . . .
 O4 O 0.54067(5) 0.6415(4) 0.89972(16) 0.0323(4) Uani 1 1 d . . . . .
 O5 O 0.70136(6) 0.1511(4) 0.8875(2) 0.0391(5) Uani 1 1 d . . . . .
 H5 H 0.7214(12) 0.223(7) 0.858(4) 0.059 Uiso 1 1 d R . . . .
 O6 O 0.72743(5) 0.8027(4) 1.20791(19) 0.0378(5) Uani 1 1 d . . . . .
 O7 O 0.44094(6) 1.1167(4) 0.7224(2) 0.0455(5) Uani 1 1 d . . . . .
 O8 O 0.43188(8) 0.7426(5) 0.6833(3) 0.0672(8) Uani 1 1 d . . . . .
 C1 C 0.66166(7) 0.4244(5) 1.0046(2) 0.0293(5) Uani 1 1 d . . . . .
 C2 C 0.66637(7) 0.2921(5) 0.8829(2) 0.0303(5) Uani 1 1 d . . . . .
 H2 H 0.6655 0.3970 0.8090 0.036 Uiso 1 1 calc R . . . .
 C3 C 0.62898(7) 0.1316(5) 0.8849(3) 0.0330(6) Uani 1 1 d . . . . .
 H3 H 0.6387 -0.0321 0.8847 0.040 Uiso 1 1 calc R . . . .
 C4 C 0.61317(8) 0.1851(5) 1.0151(3) 0.0335(6) Uani 1 1 d . . . . .
 H4 H 0.5969 0.0587 1.0519 0.040 Uiso 1 1 calc R . . . .
 C5 C 0.59223(7) 0.4199(5) 1.0082(2) 0.0288(5) Uani 1 1 d . . . . .
 H5A H 0.5792 0.4558 1.0883 0.035 Uiso 1 1 calc R . . . .
 C6 C 0.56150(7) 0.4283(5) 0.9008(2) 0.0299(5) Uani 1 1 d . . . . .
 H6 H 0.5414 0.3021 0.9126 0.036 Uiso 1 1 calc R . . . .
 C7 C 0.58212(7) 0.3844(5) 0.7790(2) 0.0322(6) Uani 1 1 d . . . . .
 H7 H 0.6037 0.5027 0.7687 0.039 Uiso 1 1 calc R . . . .
 C8 C 0.55230(8) 0.3972(6) 0.6691(3) 0.0423(7) Uani 1 1 d . . . . .
 H8A H 0.5337 0.2635 0.6703 0.051 Uiso 1 1 calc R . . . .
 H8B H 0.5669 0.3925 0.5905 0.051 Uiso 1 1 calc R . . . .
 C9 C 0.52848(9) 0.6210(6) 0.6766(3) 0.0442(7) Uani 1 1 d . . . . .
 H9A H 0.5071 0.6236 0.6099 0.053 Uiso 1 1 calc R . . . .
 H9B H 0.5467 0.7538 0.6637 0.053 Uiso 1 1 calc R . . . .
 C10 C 0.50939(7) 0.6441(5) 0.8026(2) 0.0343(6) Uani 1 1 d . . . . .
 H10 H 0.4906 0.5114 0.8147 0.041 Uiso 1 1 calc R . . . .
 C11 C 0.69766(7) 0.5605(5) 1.0531(3) 0.0337(6) Uani 1 1 d . . . . .
 H11A H 0.7065 0.6647 0.9864 0.040 Uiso 1 1 calc R . . . .
 H11B H 0.7201 0.4519 1.0730 0.040 Uiso 1 1 calc R . . . .
 C12 C 0.68983(8) 0.7030(5) 1.1674(3) 0.0356(6) Uani 1 1 d . . . . .
 H12A H 0.6698 0.8257 1.1471 0.043 Uiso 1 1 calc R . . . .
 H12B H 0.6791 0.6041 1.2336 0.043 Uiso 1 1 calc R . . . .
 C13 C 0.72374(8) 0.9759(6) 1.2998(3) 0.0400(7) Uani 1 1 d . . . . .
 H13A H 0.7070 0.9185 1.3677 0.048 Uiso 1 1 calc R . . . .
 H13B H 0.7105 1.1145 1.2630 0.048 Uiso 1 1 calc R . . . .
 C14 C 0.76538(8) 1.0364(5) 1.3504(2) 0.0318(5) Uani 1 1 d . . . . .
 C15 C 0.78420(9) 1.2417(5) 1.3209(3) 0.0389(6) Uani 1 1 d . . . . .
 H15 H 0.7707 1.3495 1.2674 0.047 Uiso 1 1 calc R . . . .
 C16 C 0.82275(9) 1.2912(6) 1.3689(3) 0.0431(7) Uani 1 1 d . . . . .
 H16 H 0.8355 1.4322 1.3476 0.052 Uiso 1 1 calc R . . . .
 C17 C 0.84258(9) 1.1371(6) 1.4470(3) 0.0461(7) Uani 1 1 d . . . . .
 H17 H 0.8688 1.1718 1.4808 0.055 Uiso 1 1 calc R . . . .
 C18 C 0.82399(10) 0.9314(6) 1.4758(3) 0.0475(7) Uani 1 1 d . . . . .
 H18 H 0.8376 0.8234 1.5291 0.057 Uiso 1 1 calc R . . . .
 C19 C 0.78583(9) 0.8816(5) 1.4278(3) 0.0393(6) Uani 1 1 d . . . . .
 H19 H 0.7734 0.7392 1.4482 0.047 Uiso 1 1 calc R . . . .
 C20 C 0.48698(8) 0.8675(6) 0.8206(3) 0.0397(6) Uani 1 1 d . . . . .
 H20A H 0.4781 0.8750 0.9073 0.048 Uiso 1 1 calc R . . . .
 H20B H 0.5057 0.9982 0.8081 0.048 Uiso 1 1 calc R . . . .
 C21 C 0.45067(8) 0.8944(6) 0.7332(3) 0.0386(6) Uani 1 1 d . . . . .
 C22 C 0.40441(10) 1.1662(7) 0.6492(3) 0.0504(8) Uani 1 1 d . . . . .
 H22A H 0.4067 1.1020 0.5654 0.076 Uiso 1 1 calc GR . . . .
 H22B H 0.4006 1.3338 0.6436 0.076 Uiso 1 1 calc GR . . . .
 H22C H 0.3813 1.0962 0.6889 0.076 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 1.427(3) . ?
 O1 C4 1.440(3) . ?
 O2 C1 1.448(3) . ?
 O2 C5 1.446(3) . ?
 O3 C3 1.428(3) . ?
 O3 C7 1.430(3) . ?
 O4 C6 1.414(3) . ?
 O4 C10 1.444(3) . ?
 O5 H5 0.85(4) . ?
 O5 C2 1.417(3) . ?
 O6 C12 1.426(3) . ?
 O6 C13 1.417(4) . ?
 O7 C21 1.331(4) . ?
 O7 C22 1.447(4) . ?
 O8 C21 1.193(4) . ?
 C1 C2 1.530(4) . ?
 C1 C11 1.506(4) . ?
 C2 H2 1.0000 . ?
 C2 C3 1.549(3) . ?
 C3 H3 1.0000 . ?
 C3 C4 1.545(4) . ?
 C4 H4 1.0000 . ?
 C4 C5 1.526(4) . ?
 C5 H5A 1.0000 . ?
 C5 C6 1.512(3) . ?
 C6 H6 1.0000 . ?
 C6 C7 1.521(3) . ?
 C7 H7 1.0000 . ?
 C7 C8 1.514(4) . ?
 C8 H8A 0.9900 . ?
 C8 H8B 0.9900 . ?
 C8 C9 1.520(5) . ?
 C9 H9A 0.9900 . ?
 C9 H9B 0.9900 . ?
 C9 C10 1.523(4) . ?
 C10 H10 1.0000 . ?
 C10 C20 1.507(4) . ?
 C11 H11A 0.9900 . ?
 C11 H11B 0.9900 . ?
 C11 C12 1.511(4) . ?
 C12 H12A 0.9900 . ?
 C12 H12B 0.9900 . ?
 C13 H13A 0.9900 . ?
 C13 H13B 0.9900 . ?
 C13 C14 1.505(4) . ?
 C14 C15 1.384(4) . ?
 C14 C19 1.384(4) . ?
 C15 H15 0.9500 . ?
 C15 C16 1.389(4) . ?
 C16 H16 0.9500 . ?
 C16 C17 1.375(5) . ?
 C17 H17 0.9500 . ?
 C17 C18 1.382(5) . ?
 C18 H18 0.9500 . ?
 C18 C19 1.378(4) . ?
 C19 H19 0.9500 . ?
 C20 H20A 0.9900 . ?
 C20 H20B 0.9900 . ?
 C20 C21 1.507(4) . ?
 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
 C1 O1 C4 95.82(18) . . ?
 C5 O2 C1 105.42(18) . . ?
 C3 O3 C7 113.5(2) . . ?
 C6 O4 C10 110.6(2) . . ?
 C2 O5 H5 111(3) . . ?
 C13 O6 C12 113.7(2) . . ?
 C21 O7 C22 115.7(3) . . ?
 O1 C1 O2 103.65(17) . . ?
 O1 C1 C2 102.0(2) . . ?
 O1 C1 C11 114.0(2) . . ?
 O2 C1 C2 108.1(2) . . ?
 O2 C1 C11 110.9(2) . . ?
 C11 C1 C2 116.9(2) . . ?
 O5 C2 C1 111.6(2) . . ?
 O5 C2 H2 112.1 . . ?
 O5 C2 C3 107.9(2) . . ?
 C1 C2 H2 112.1 . . ?
 C1 C2 C3 100.40(19) . . ?
 C3 C2 H2 112.1 . . ?
 O3 C3 C2 115.7(2) . . ?
 O3 C3 H3 108.2 . . ?
 O3 C3 C4 115.1(2) . . ?
 C2 C3 H3 108.2 . . ?
 C4 C3 C2 101.0(2) . . ?
 C4 C3 H3 108.2 . . ?
 O1 C4 C3 103.30(19) . . ?
 O1 C4 H4 114.8 . . ?
 O1 C4 C5 100.0(2) . . ?
 C3 C4 H4 114.8 . . ?
 C5 C4 C3 107.7(2) . . ?
 C5 C4 H4 114.8 . . ?
 O2 C5 C4 100.81(18) . . ?
 O2 C5 H5A 110.7 . . ?
 O2 C5 C6 112.7(2) . . ?
 C4 C5 H5A 110.7 . . ?
 C6 C5 C4 110.9(2) . . ?
 C6 C5 H5A 110.7 . . ?
 O4 C6 C5 110.4(2) . . ?
 O4 C6 H6 108.1 . . ?
 O4 C6 C7 112.0(2) . . ?
 C5 C6 H6 108.1 . . ?
 C5 C6 C7 109.96(19) . . ?
 C7 C6 H6 108.1 . . ?
 O3 C7 C6 108.6(2) . . ?
 O3 C7 H7 109.2 . . ?
 O3 C7 C8 109.5(2) . . ?
 C6 C7 H7 109.2 . . ?
 C8 C7 C6 111.3(2) . . ?
 C8 C7 H7 109.2 . . ?
 C7 C8 H8A 109.9 . . ?
 C7 C8 H8B 109.9 . . ?
 C7 C8 C9 109.0(2) . . ?
 H8A C8 H8B 108.3 . . ?
 C9 C8 H8A 109.9 . . ?
 C9 C8 H8B 109.9 . . ?
 C8 C9 H9A 109.5 . . ?
 C8 C9 H9B 109.5 . . ?
 C8 C9 C10 110.9(3) . . ?
 H9A C9 H9B 108.1 . . ?
 C10 C9 H9A 109.5 . . ?
 C10 C9 H9B 109.5 . . ?
 O4 C10 C9 109.4(2) . . ?
 O4 C10 H10 109.3 . . ?
 O4 C10 C20 105.0(2) . . ?
 C9 C10 H10 109.3 . . ?
 C20 C10 C9 114.4(3) . . ?
 C20 C10 H10 109.3 . . ?
 C1 C11 H11A 108.7 . . ?
 C1 C11 H11B 108.7 . . ?
 C1 C11 C12 114.1(2) . . ?
 H11A C11 H11B 107.6 . . ?
 C12 C11 H11A 108.7 . . ?
 C12 C11 H11B 108.7 . . ?
 O6 C12 C11 107.1(2) . . ?
 O6 C12 H12A 110.3 . . ?
 O6 C12 H12B 110.3 . . ?
 C11 C12 H12A 110.3 . . ?
 C11 C12 H12B 110.3 . . ?
 H12A C12 H12B 108.5 . . ?
 O6 C13 H13A 110.0 . . ?
 O6 C13 H13B 110.0 . . ?
 O6 C13 C14 108.3(2) . . ?
 H13A C13 H13B 108.4 . . ?
 C14 C13 H13A 110.0 . . ?
 C14 C13 H13B 110.0 . . ?
 C15 C14 C13 122.1(3) . . ?
 C19 C14 C13 119.2(3) . . ?
 C19 C14 C15 118.7(3) . . ?
 C14 C15 H15 119.7 . . ?
 C14 C15 C16 120.5(3) . . ?
 C16 C15 H15 119.7 . . ?
 C15 C16 H16 119.9 . . ?
 C17 C16 C15 120.3(3) . . ?
 C17 C16 H16 119.9 . . ?
 C16 C17 H17 120.3 . . ?
 C16 C17 C18 119.3(3) . . ?
 C18 C17 H17 120.3 . . ?
 C17 C18 H18 119.8 . . ?
 C19 C18 C17 120.5(3) . . ?
 C19 C18 H18 119.8 . . ?
 C14 C19 H19 119.6 . . ?
 C18 C19 C14 120.8(3) . . ?
 C18 C19 H19 119.6 . . ?
 C10 C20 H20A 108.9 . . ?
 C10 C20 H20B 108.9 . . ?
 H20A C20 H20B 107.8 . . ?
 C21 C20 C10 113.2(3) . . ?
 C21 C20 H20A 108.9 . . ?
 C21 C20 H20B 108.9 . . ?
 O7 C21 C20 109.9(3) . . ?
 O8 C21 O7 123.5(3) . . ?
 O8 C21 C20 126.6(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
 O5 H5 O6 0.85(4) 1.92(4) 2.752(3) 165(4) 4_647

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 O5 -73.4(2) . . . . ?
 O1 C1 C2 C3 40.7(2) . . . . ?
 O1 C1 C11 C12 -66.1(3) . . . . ?
 O1 C4 C5 O2 39.5(2) . . . . ?
 O1 C4 C5 C6 159.08(19) . . . . ?
 O2 C1 C2 O5 177.68(19) . . . . ?
 O2 C1 C2 C3 -68.2(2) . . . . ?
 O2 C1 C11 C12 50.5(3) . . . . ?
 O2 C5 C6 O4 -71.2(2) . . . . ?
 O2 C5 C6 C7 52.8(3) . . . . ?
 O3 C3 C4 O1 -154.9(2) . . . . ?
 O3 C3 C4 C5 -49.7(3) . . . . ?
 O3 C7 C8 C9 170.8(2) . . . . ?
 O4 C6 C7 O3 -176.12(19) . . . . ?
 O4 C6 C7 C8 -55.5(3) . . . . ?
 O4 C10 C20 C21 -175.5(2) . . . . ?
 O5 C2 C3 O3 -124.3(2) . . . . ?
 O5 C2 C3 C4 110.7(2) . . . . ?
 O6 C13 C14 C15 106.5(3) . . . . ?
 O6 C13 C14 C19 -72.8(3) . . . . ?
 C1 O1 C4 C3 55.1(2) . . . . ?
 C1 O1 C4 C5 -55.9(2) . . . . ?
 C1 O2 C5 C4 -7.1(2) . . . . ?
 C1 O2 C5 C6 -125.4(2) . . . . ?
 C1 C2 C3 O3 118.8(2) . . . . ?
 C1 C2 C3 C4 -6.2(2) . . . . ?
 C1 C11 C12 O6 174.6(2) . . . . ?
 C2 C1 C11 C12 175.0(2) . . . . ?
 C2 C3 C4 O1 -29.5(3) . . . . ?
 C2 C3 C4 C5 75.7(2) . . . . ?
 C3 O3 C7 C6 -58.7(2) . . . . ?
 C3 O3 C7 C8 179.6(2) . . . . ?
 C3 C4 C5 O2 -68.0(2) . . . . ?
 C3 C4 C5 C6 51.6(3) . . . . ?
 C4 O1 C1 O2 52.6(2) . . . . ?
 C4 O1 C1 C2 -59.6(2) . . . . ?
 C4 O1 C1 C11 173.3(2) . . . . ?
 C4 C5 C6 O4 176.59(18) . . . . ?
 C4 C5 C6 C7 -59.4(3) . . . . ?
 C5 O2 C1 O1 -28.2(2) . . . . ?
 C5 O2 C1 C2 79.6(2) . . . . ?
 C5 O2 C1 C11 -151.0(2) . . . . ?
 C5 C6 C7 O3 60.8(3) . . . . ?
 C5 C6 C7 C8 -178.6(2) . . . . ?
 C6 O4 C10 C9 -62.7(3) . . . . ?
 C6 O4 C10 C20 174.1(2) . . . . ?
 C6 C7 C8 C9 50.8(3) . . . . ?
 C7 O3 C3 C2 -62.1(3) . . . . ?
 C7 O3 C3 C4 55.4(3) . . . . ?
 C7 C8 C9 C10 -53.5(3) . . . . ?
 C8 C9 C10 O4 59.4(3) . . . . ?
 C8 C9 C10 C20 176.9(2) . . . . ?
 C9 C10 C20 C21 64.5(3) . . . . ?
 C10 O4 C6 C5 -176.02(19) . . . . ?
 C10 O4 C6 C7 61.1(2) . . . . ?
 C10 C20 C21 O7 -158.3(2) . . . . ?
 C10 C20 C21 O8 24.2(4) . . . . ?
 C11 C1 C2 O5 51.7(3) . . . . ?
 C11 C1 C2 C3 165.8(2) . . . . ?
 C12 O6 C13 C14 170.2(2) . . . . ?
 C13 O6 C12 C11 168.6(2) . . . . ?
 C13 C14 C15 C16 -179.7(3) . . . . ?
 C13 C14 C19 C18 -180.0(3) . . . . ?
 C14 C15 C16 C17 -0.4(5) . . . . ?
 C15 C14 C19 C18 0.7(4) . . . . ?
 C15 C16 C17 C18 0.9(5) . . . . ?
 C16 C17 C18 C19 -0.6(5) . . . . ?
 C17 C18 C19 C14 -0.2(5) . . . . ?
 C19 C14 C15 C16 -0.4(4) . . . . ?
 C22 O7 C21 O8 2.6(4) . . . . ?
 C22 O7 C21 C20 -175.0(2) . . . . ?

_contact_Crystallographer_email   staples@chemistry.msu.com
_contact_Crystallographer_name    'Richard Staples'
_journal_coden_cambridge          1078
_journal_name_full                'Private Communication'
_journal_page_first               1
_journal_page_last                2
_journal_volume                   1MSU
_journal_year                     2015
_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_special_instructions 'No special instructions were received'

