data_cu_20220427_cph_04_25_coome_0m
_audit_creation_date               2022-04-28
_audit_creation_method
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number       '2018/3'
_audit_contact_author_address      ?
_audit_contact_author_email        ?
_audit_contact_author_name         ''
_audit_contact_author_phone        ?
_publ_contact_author_id_orcid      ?
_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. (2015). Acta Cryst. A71, 3-8.

Sheldrick, G.M. (2015). Acta Cryst. C71, 3-8.
;
_chemical_name_common              ?
_chemical_name_systematic          ?
_chemical_formula_moiety           'C23 H30 O11'
_chemical_formula_sum              'C23 H30 O11'
_chemical_formula_weight           482.47
_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        'orthorhombic'
_space_group_IT_number             19
_space_group_name_H-M_alt          'P 21 21 21'
_space_group_name_Hall             'P 2ac 2ab'
loop_
  _space_group_symop_operation_xyz
 'x, y, z'
 '-x+1/2, -y, z+1/2'
 '-x, y+1/2, -z+1/2'
 'x+1/2, -y+1/2, -z'

_cell_length_a                     6.01470(10)
_cell_length_b                     17.5833(3)
_cell_length_c                     23.3786(4)
_cell_angle_alpha                  90
_cell_angle_beta                   90
_cell_angle_gamma                  90
_cell_volume                       2472.48(7)
_cell_formula_units_Z              4
_cell_measurement_reflns_used      9697
_cell_measurement_temperature      193.00
_cell_measurement_theta_max        68.097
_cell_measurement_theta_min        3.781
_shelx_estimated_absorpt_T_max     0.894
_shelx_estimated_absorpt_T_min     0.872
_exptl_absorpt_coefficient_mu      0.879
_exptl_absorpt_correction_T_max    0.4672
_exptl_absorpt_correction_T_min    0.3532
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1475 before and 0.0778 after correction.
The Ratio of minimum to maximum transmission is 0.7560.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details     ?
_exptl_crystal_colour              ?
_exptl_crystal_density_diffrn      1.296
_exptl_crystal_density_meas        ?
_exptl_crystal_density_method      ?
_exptl_crystal_description         block
_exptl_crystal_F_000               1024
_exptl_crystal_size_max            0.16
_exptl_crystal_size_mid            0.15
_exptl_crystal_size_min            0.13
_exptl_transmission_factor_max     ?
_exptl_transmission_factor_min     ?
_diffrn_reflns_av_R_equivalents    0.0611
_diffrn_reflns_av_unetI/netI       0.0282
_diffrn_reflns_Laue_measured_fraction_full  0.998
_diffrn_reflns_Laue_measured_fraction_max  0.998
_diffrn_reflns_limit_h_max         7
_diffrn_reflns_limit_h_min         -7
_diffrn_reflns_limit_k_max         21
_diffrn_reflns_limit_k_min         -21
_diffrn_reflns_limit_l_max         28
_diffrn_reflns_limit_l_min         -28
_diffrn_reflns_number              46180
_diffrn_reflns_point_group_measured_fraction_full  0.999
_diffrn_reflns_point_group_measured_fraction_max  0.999
_diffrn_reflns_theta_full          67.679
_diffrn_reflns_theta_max           68.172
_diffrn_reflns_theta_min           3.781
_diffrn_ambient_temperature        193.00
_diffrn_detector_area_resol_mean   ?
_diffrn_measured_fraction_theta_full  0.998
_diffrn_measured_fraction_theta_max  0.998
_diffrn_measurement_device_type    'Bruker D8 VENTURE'
_diffrn_measurement_method         'φ and ω scans'
_diffrn_radiation_type             CuK\a
_diffrn_radiation_wavelength       1.54178
_diffrn_source                     ?
_diffrn_source_current             1.1
_diffrn_source_power               0.05500000000000001
_diffrn_source_voltage             50.0
_diffrn_standards_number           0
_reflns_Friedel_coverage           0.726
_reflns_Friedel_fraction_full      1.000
_reflns_Friedel_fraction_max       1.000
_reflns_number_gt                  4310
_reflns_number_total               4521
_reflns_special_details
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 Structure factors included contributions from the .fab file.
 
 _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 v8.37A (Bruker, 2015)'
_computing_data_collection         ?
_computing_data_reduction          'SAINT v8.37A (Bruker, 2015)'
_computing_molecular_graphics      'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement    'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution      'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max           0.273
_refine_diff_density_min           -0.311
_refine_diff_density_rms           0.078
_refine_ls_abs_structure_details
;
 Flack x determined using 1773 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack     0.07(5)
_refine_ls_extinction_coef         0.0094(8)
_refine_ls_extinction_expression  
 'Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^'
_refine_ls_extinction_method       'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref     1.118
_refine_ls_hydrogen_treatment      constr
_refine_ls_matrix_type             full
_refine_ls_number_parameters       315
_refine_ls_number_reflns           4521
_refine_ls_number_restraints       0
_refine_ls_R_factor_all            0.0437
_refine_ls_R_factor_gt             0.0421
_refine_ls_restrained_S_all        1.118
_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)+(0.0716P)²+0.4994P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme        calc
_refine_ls_wR_factor_gt            0.1115
_refine_ls_wR_factor_ref           0.1130
_refine_special_details            ?
_olex2_refinement_description
;
1.a Ternary CH refined with riding coordinates:
 C4(H4), C5(H5), C7(H7A), C8(H8), C9(H9)
1.b Secondary CH2 refined with riding coordinates:
 C13(H13A,H13B), C16(H16A,H16B), C17(H17A,H17B)
1.c Idealised Me refined as rotating group:
 C2(H2A,H2B,H2C), C3(H3A,H3B,H3C), C12(H12A,H12B,H12C), C20(H20A,H20B,H20C),
 C22(H22A,H22B,H22C), C23(H23A,H23B,H23C)
1.d Idealised tetrahedral OH refined as rotating group:
 O7(H7)
;
_atom_sites_solution_hydrogens     geom
_atom_sites_solution_primary       dual
_atom_sites_solution_secondary     ?
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 0.7174(3) 0.21541(10) 0.35411(8) 0.0311(4) Uani 1 1 d . . . . .
 O2 O 0.6292(4) 0.13012(10) 0.28576(8) 0.0364(5) Uani 1 1 d . . . . .
 O3 O 0.3420(3) 0.26259(10) 0.28758(8) 0.0275(4) Uani 1 1 d . . . . .
 O4 O 0.0683(4) 0.29144(12) 0.18007(10) 0.0444(5) Uani 1 1 d . . . . .
 O5 O 0.2720(4) 0.37701(12) 0.13254(9) 0.0423(5) Uani 1 1 d . . . . .
 O6 O 0.2303(4) 0.44004(11) 0.24800(9) 0.0375(5) Uani 1 1 d . . . . .
 O7 O 0.5668(4) 0.49271(10) 0.23497(10) 0.0406(5) Uani 1 1 d . . . . .
 H7 H 0.492934 0.533159 0.232788 0.061 Uiso 1 1 calc R U . . .
 O8 O 0.5483(3) 0.43130(10) 0.35898(7) 0.0264(4) Uani 1 1 d . . . . .
 O9 O 0.8877(4) 0.38585(13) 0.37803(13) 0.0587(7) Uani 1 1 d . . . . .
 O10 O 0.6453(3) 0.57163(10) 0.38204(8) 0.0300(4) Uani 1 1 d . . . . .
 O11 O 0.5947(3) 0.69042(12) 0.41470(10) 0.0427(5) Uani 1 1 d . . . . .
 C1 C 0.7397(5) 0.13680(15) 0.33997(12) 0.0325(6) Uani 1 1 d . . . . .
 C2 C 0.6108(5) 0.09070(17) 0.38340(14) 0.0407(7) Uani 1 1 d . . . . .
 H2A H 0.680253 0.096108 0.421105 0.061 Uiso 1 1 calc R U . . .
 H2B H 0.611548 0.037012 0.372137 0.061 Uiso 1 1 calc R U . . .
 H2C H 0.457157 0.109103 0.385107 0.061 Uiso 1 1 calc R U . . .
 C3 C 0.9811(6) 0.11412(19) 0.33421(17) 0.0485(8) Uani 1 1 d . . . . .
 H3A H 0.990640 0.062847 0.317949 0.073 Uiso 1 1 calc R U . . .
 H3B H 1.051714 0.114669 0.371984 0.073 Uiso 1 1 calc R U . . .
 H3C H 1.057476 0.150129 0.308958 0.073 Uiso 1 1 calc R U . . .
 C4 C 0.6579(5) 0.20000(14) 0.25533(12) 0.0297(6) Uani 1 1 d . . . . .
 H4 H 0.768737 0.196576 0.223544 0.036 Uiso 1 1 calc R U . . .
 C5 C 0.7231(4) 0.25825(14) 0.30248(11) 0.0258(5) Uani 1 1 d . . . . .
 H5 H 0.869216 0.283720 0.295392 0.031 Uiso 1 1 calc R U . . .
 C6 C 0.5230(4) 0.31317(14) 0.30013(11) 0.0238(5) Uani 1 1 d . . . . .
 C7 C 0.4319(5) 0.22964(14) 0.23630(11) 0.0303(6) Uani 1 1 d . . . . .
 H7A H 0.334547 0.189827 0.218826 0.036 Uiso 1 1 calc R U . . .
 C8 C 0.4640(5) 0.30028(15) 0.19833(11) 0.0304(6) Uani 1 1 d . . . . .
 H8 H 0.578766 0.290115 0.168353 0.036 Uiso 1 1 calc R U . . .
 C9 C 0.5546(5) 0.35960(13) 0.24334(10) 0.0264(5) Uani 1 1 d . . . . .
 H9 H 0.716435 0.369003 0.236511 0.032 Uiso 1 1 calc R U . . .
 C10 C 0.4294(5) 0.43433(14) 0.24269(11) 0.0286(5) Uani 1 1 d . . . . .
 C11 C 0.2429(5) 0.32106(15) 0.17056(12) 0.0347(6) Uani 1 1 d . . . . .
 C12 C 0.0670(7) 0.4026(2) 0.10674(16) 0.0546(9) Uani 1 1 d . . . . .
 H12A H 0.098804 0.443473 0.079448 0.082 Uiso 1 1 calc R U . . .
 H12B H -0.033084 0.421613 0.136581 0.082 Uiso 1 1 calc R U . . .
 H12C H -0.003948 0.360076 0.086706 0.082 Uiso 1 1 calc R U . . .
 C13 C 0.4611(4) 0.35453(14) 0.35453(11) 0.0269(5) Uani 1 1 d . . . . .
 H13A H 0.296977 0.356757 0.357252 0.032 Uiso 1 1 calc R U . . .
 H13B H 0.515672 0.324605 0.387544 0.032 Uiso 1 1 calc R U . . .
 C14 C 0.7605(5) 0.43815(15) 0.37339(12) 0.0313(6) Uani 1 1 d . . . . .
 C15 C 0.8331(4) 0.51845(15) 0.38505(11) 0.0266(5) Uani 1 1 d . . . . .
 C16 C 1.0098(5) 0.55077(17) 0.34501(12) 0.0355(6) Uani 1 1 d . . . . .
 H16A H 0.946661 0.563523 0.307101 0.043 Uiso 1 1 calc R U . . .
 H16B H 1.135221 0.514904 0.339994 0.043 Uiso 1 1 calc R U . . .
 C17 C 1.0822(5) 0.62255(16) 0.37758(13) 0.0346(6) Uani 1 1 d . . . . .
 H17A H 1.049161 0.668895 0.355090 0.041 Uiso 1 1 calc R U . . .
 H17B H 1.243342 0.621124 0.386100 0.041 Uiso 1 1 calc R U . . .
 C18 C 0.9437(4) 0.62085(15) 0.43350(11) 0.0285(6) Uani 1 1 d . . . . .
 C19 C 0.7110(4) 0.63518(15) 0.41152(12) 0.0288(6) Uani 1 1 d . . . . .
 C20 C 1.0198(6) 0.67394(19) 0.48037(16) 0.0460(8) Uani 1 1 d . . . . .
 H20A H 1.012403 0.726569 0.466698 0.069 Uiso 1 1 calc R U . . .
 H20B H 1.173306 0.661672 0.490984 0.069 Uiso 1 1 calc R U . . .
 H20C H 0.923163 0.668028 0.513817 0.069 Uiso 1 1 calc R U . . .
 C21 C 0.9278(4) 0.53413(14) 0.44592(11) 0.0253(5) Uani 1 1 d . . . . .
 C22 C 1.1502(5) 0.49641(17) 0.45811(13) 0.0350(6) Uani 1 1 d . . . . .
 H22A H 1.254341 0.507947 0.427055 0.053 Uiso 1 1 calc R U . . .
 H22B H 1.129702 0.441241 0.460827 0.053 Uiso 1 1 calc R U . . .
 H22C H 1.209964 0.515738 0.494294 0.053 Uiso 1 1 calc R U . . .
 C23 C 0.7635(5) 0.51462(19) 0.49408(13) 0.0406(7) Uani 1 1 d . . . . .
 H23A H 0.825223 0.531036 0.530854 0.061 Uiso 1 1 calc R U . . .
 H23B H 0.738294 0.459570 0.494847 0.061 Uiso 1 1 calc R U . . .
 H23C H 0.622159 0.540829 0.487239 0.061 Uiso 1 1 calc R U . . .


_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 C5 1.423(3) . ?
 O2 C1 1.436(3) . ?
 O2 C4 1.430(3) . ?
 O3 C6 1.436(3) . ?
 O3 C7 1.437(3) . ?
 O4 C11 1.193(4) . ?
 O5 C11 1.337(3) . ?
 O5 C12 1.445(4) . ?
 O6 C10 1.208(4) . ?
 O7 H7 0.8400 . ?
 O7 C10 1.330(3) . ?
 O8 C13 1.452(3) . ?
 O8 C14 1.326(3) . ?
 O9 C14 1.201(3) . ?
 O10 C15 1.468(3) . ?
 O10 C19 1.371(3) . ?
 O11 C19 1.199(3) . ?
 C1 C2 1.513(4) . ?
 C1 C3 1.512(4) . ?
 C2 H2A 0.9800 . ?
 C2 H2B 0.9800 . ?
 C2 H2C 0.9800 . ?
 C3 H3A 0.9800 . ?
 C3 H3B 0.9800 . ?
 C3 H3C 0.9800 . ?
 C4 H4 1.0000 . ?
 C4 C5 1.555(3) . ?
 C4 C7 1.522(4) . ?
 C5 H5 1.0000 . ?
 C5 C6 1.544(3) . ?
 C6 C9 1.570(3) . ?
 C6 C13 1.512(3) . ?
 C7 H7A 1.0000 . ?
 C7 C8 1.539(4) . ?
 C8 H8 1.0000 . ?
 C8 C9 1.579(3) . ?
 C8 C11 1.524(4) . ?
 C9 H9 1.0000 . ?
 C9 C10 1.515(3) . ?
 C12 H12A 0.9800 . ?
 C12 H12B 0.9800 . ?
 C12 H12C 0.9800 . ?
 C13 H13A 0.9900 . ?
 C13 H13B 0.9900 . ?
 C14 C15 1.503(4) . ?
 C15 C16 1.526(4) . ?
 C15 C21 1.557(3) . ?
 C16 H16A 0.9900 . ?
 C16 H16B 0.9900 . ?
 C16 C17 1.537(4) . ?
 C17 H17A 0.9900 . ?
 C17 H17B 0.9900 . ?
 C17 C18 1.550(4) . ?
 C18 C19 1.512(4) . ?
 C18 C20 1.510(4) . ?
 C18 C21 1.555(4) . ?
 C20 H20A 0.9800 . ?
 C20 H20B 0.9800 . ?
 C20 H20C 0.9800 . ?
 C21 C22 1.520(4) . ?
 C21 C23 1.537(4) . ?
 C22 H22A 0.9800 . ?
 C22 H22B 0.9800 . ?
 C22 H22C 0.9800 . ?
 C23 H23A 0.9800 . ?
 C23 H23B 0.9800 . ?
 C23 H23C 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 108.29(19) . . ?
 C4 O2 C1 108.2(2) . . ?
 C6 O3 C7 97.75(18) . . ?
 C11 O5 C12 113.3(3) . . ?
 C10 O7 H7 109.5 . . ?
 C14 O8 C13 116.8(2) . . ?
 C19 O10 C15 105.86(19) . . ?
 O1 C1 O2 103.9(2) . . ?
 O1 C1 C2 108.4(2) . . ?
 O1 C1 C3 111.5(3) . . ?
 O2 C1 C2 108.2(2) . . ?
 O2 C1 C3 110.1(3) . . ?
 C3 C1 C2 114.2(3) . . ?
 C1 C2 H2A 109.5 . . ?
 C1 C2 H2B 109.5 . . ?
 C1 C2 H2C 109.5 . . ?
 H2A C2 H2B 109.5 . . ?
 H2A C2 H2C 109.5 . . ?
 H2B C2 H2C 109.5 . . ?
 C1 C3 H3A 109.5 . . ?
 C1 C3 H3B 109.5 . . ?
 C1 C3 H3C 109.5 . . ?
 H3A C3 H3B 109.5 . . ?
 H3A C3 H3C 109.5 . . ?
 H3B C3 H3C 109.5 . . ?
 O2 C4 H4 113.5 . . ?
 O2 C4 C5 104.1(2) . . ?
 O2 C4 C7 109.4(2) . . ?
 C5 C4 H4 113.5 . . ?
 C7 C4 H4 113.5 . . ?
 C7 C4 C5 101.9(2) . . ?
 O1 C5 C4 104.26(19) . . ?
 O1 C5 H5 113.5 . . ?
 O1 C5 C6 110.0(2) . . ?
 C4 C5 H5 113.5 . . ?
 C6 C5 C4 101.0(2) . . ?
 C6 C5 H5 113.5 . . ?
 O3 C6 C5 102.17(19) . . ?
 O3 C6 C9 103.95(19) . . ?
 O3 C6 C13 106.5(2) . . ?
 C5 C6 C9 105.1(2) . . ?
 C13 C6 C5 117.6(2) . . ?
 C13 C6 C9 119.4(2) . . ?
 O3 C7 C4 103.3(2) . . ?
 O3 C7 H7A 113.7 . . ?
 O3 C7 C8 101.7(2) . . ?
 C4 C7 H7A 113.7 . . ?
 C4 C7 C8 109.5(2) . . ?
 C8 C7 H7A 113.7 . . ?
 C7 C8 H8 110.3 . . ?
 C7 C8 C9 101.1(2) . . ?
 C9 C8 H8 110.3 . . ?
 C11 C8 C7 109.3(2) . . ?
 C11 C8 H8 110.3 . . ?
 C11 C8 C9 115.3(2) . . ?
 C6 C9 C8 100.27(19) . . ?
 C6 C9 H9 109.8 . . ?
 C8 C9 H9 109.8 . . ?
 C10 C9 C6 113.5(2) . . ?
 C10 C9 C8 113.2(2) . . ?
 C10 C9 H9 109.8 . . ?
 O6 C10 O7 124.4(2) . . ?
 O6 C10 C9 124.3(3) . . ?
 O7 C10 C9 111.2(2) . . ?
 O4 C11 O5 124.1(3) . . ?
 O4 C11 C8 125.7(2) . . ?
 O5 C11 C8 110.2(2) . . ?
 O5 C12 H12A 109.5 . . ?
 O5 C12 H12B 109.5 . . ?
 O5 C12 H12C 109.5 . . ?
 H12A C12 H12B 109.5 . . ?
 H12A C12 H12C 109.5 . . ?
 H12B C12 H12C 109.5 . . ?
 O8 C13 C6 114.7(2) . . ?
 O8 C13 H13A 108.6 . . ?
 O8 C13 H13B 108.6 . . ?
 C6 C13 H13A 108.6 . . ?
 C6 C13 H13B 108.6 . . ?
 H13A C13 H13B 107.6 . . ?
 O8 C14 C15 114.3(2) . . ?
 O9 C14 O8 124.5(3) . . ?
 O9 C14 C15 121.2(2) . . ?
 O10 C15 C14 111.5(2) . . ?
 O10 C15 C16 105.6(2) . . ?
 O10 C15 C21 102.27(18) . . ?
 C14 C15 C16 116.1(2) . . ?
 C14 C15 C21 116.0(2) . . ?
 C16 C15 C21 103.9(2) . . ?
 C15 C16 H16A 111.5 . . ?
 C15 C16 H16B 111.5 . . ?
 C15 C16 C17 101.5(2) . . ?
 H16A C16 H16B 109.3 . . ?
 C17 C16 H16A 111.5 . . ?
 C17 C16 H16B 111.5 . . ?
 C16 C17 H17A 110.9 . . ?
 C16 C17 H17B 110.9 . . ?
 C16 C17 C18 104.5(2) . . ?
 H17A C17 H17B 108.9 . . ?
 C18 C17 H17A 110.9 . . ?
 C18 C17 H17B 110.9 . . ?
 C17 C18 C21 102.1(2) . . ?
 C19 C18 C17 102.0(2) . . ?
 C19 C18 C21 99.8(2) . . ?
 C20 C18 C17 115.9(2) . . ?
 C20 C18 C19 115.1(2) . . ?
 C20 C18 C21 119.3(2) . . ?
 O10 C19 C18 107.6(2) . . ?
 O11 C19 O10 121.5(2) . . ?
 O11 C19 C18 130.8(3) . . ?
 C18 C20 H20A 109.5 . . ?
 C18 C20 H20B 109.5 . . ?
 C18 C20 H20C 109.5 . . ?
 H20A C20 H20B 109.5 . . ?
 H20A C20 H20C 109.5 . . ?
 H20B C20 H20C 109.5 . . ?
 C18 C21 C15 91.46(19) . . ?
 C22 C21 C15 114.6(2) . . ?
 C22 C21 C18 114.1(2) . . ?
 C22 C21 C23 109.3(2) . . ?
 C23 C21 C15 113.2(2) . . ?
 C23 C21 C18 113.3(2) . . ?
 C21 C22 H22A 109.5 . . ?
 C21 C22 H22B 109.5 . . ?
 C21 C22 H22C 109.5 . . ?
 H22A C22 H22B 109.5 . . ?
 H22A C22 H22C 109.5 . . ?
 H22B C22 H22C 109.5 . . ?
 C21 C23 H23A 109.5 . . ?
 C21 C23 H23B 109.5 . . ?
 C21 C23 H23C 109.5 . . ?
 H23A C23 H23B 109.5 . . ?
 H23A C23 H23C 109.5 . . ?
 H23B C23 H23C 109.5 . . ?

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 C5 C6 O3 -74.5(2) . . . . ?
 O1 C5 C6 C9 177.20(19) . . . . ?
 O1 C5 C6 C13 41.6(3) . . . . ?
 O2 C4 C5 O1 -1.7(3) . . . . ?
 O2 C4 C5 C6 -115.8(2) . . . . ?
 O2 C4 C7 O3 78.0(2) . . . . ?
 O2 C4 C7 C8 -174.2(2) . . . . ?
 O3 C6 C9 C8 -27.1(2) . . . . ?
 O3 C6 C9 C10 94.0(2) . . . . ?
 O3 C6 C13 O8 -148.9(2) . . . . ?
 O3 C7 C8 C9 40.4(3) . . . . ?
 O3 C7 C8 C11 -81.5(2) . . . . ?
 O8 C14 C15 O10 4.4(3) . . . . ?
 O8 C14 C15 C16 -116.7(3) . . . . ?
 O8 C14 C15 C21 120.9(2) . . . . ?
 O9 C14 C15 O10 -174.5(3) . . . . ?
 O9 C14 C15 C16 64.4(4) . . . . ?
 O9 C14 C15 C21 -58.0(4) . . . . ?
 O10 C15 C16 C17 69.2(2) . . . . ?
 O10 C15 C21 C18 -52.7(2) . . . . ?
 O10 C15 C21 C22 -170.2(2) . . . . ?
 O10 C15 C21 C23 63.5(3) . . . . ?
 C1 O1 C5 C4 21.6(3) . . . . ?
 C1 O1 C5 C6 129.1(2) . . . . ?
 C1 O2 C4 C5 -18.7(3) . . . . ?
 C1 O2 C4 C7 -127.0(2) . . . . ?
 C4 O2 C1 O1 32.2(3) . . . . ?
 C4 O2 C1 C2 147.2(2) . . . . ?
 C4 O2 C1 C3 -87.3(3) . . . . ?
 C4 C5 C6 O3 35.2(2) . . . . ?
 C4 C5 C6 C9 -73.1(2) . . . . ?
 C4 C5 C6 C13 151.3(2) . . . . ?
 C4 C7 C8 C9 -68.4(3) . . . . ?
 C4 C7 C8 C11 169.7(2) . . . . ?
 C5 O1 C1 O2 -33.4(3) . . . . ?
 C5 O1 C1 C2 -148.3(2) . . . . ?
 C5 O1 C1 C3 85.2(3) . . . . ?
 C5 C4 C7 O3 -31.7(2) . . . . ?
 C5 C4 C7 C8 76.0(2) . . . . ?
 C5 C6 C9 C8 79.9(2) . . . . ?
 C5 C6 C9 C10 -159.0(2) . . . . ?
 C5 C6 C13 O8 97.4(3) . . . . ?
 C6 O3 C7 C4 54.8(2) . . . . ?
 C6 O3 C7 C8 -58.7(2) . . . . ?
 C6 C9 C10 O6 -59.1(3) . . . . ?
 C6 C9 C10 O7 121.5(2) . . . . ?
 C7 O3 C6 C5 -55.8(2) . . . . ?
 C7 O3 C6 C9 53.4(2) . . . . ?
 C7 O3 C6 C13 -179.7(2) . . . . ?
 C7 C4 C5 O1 112.1(2) . . . . ?
 C7 C4 C5 C6 -2.1(2) . . . . ?
 C7 C8 C9 C6 -7.7(3) . . . . ?
 C7 C8 C9 C10 -129.0(2) . . . . ?
 C7 C8 C11 O4 5.6(4) . . . . ?
 C7 C8 C11 O5 -173.2(2) . . . . ?
 C8 C9 C10 O6 54.4(3) . . . . ?
 C8 C9 C10 O7 -125.0(2) . . . . ?
 C9 C6 C13 O8 -31.8(3) . . . . ?
 C9 C8 C11 O4 -107.4(3) . . . . ?
 C9 C8 C11 O5 73.9(3) . . . . ?
 C11 C8 C9 C6 109.9(2) . . . . ?
 C11 C8 C9 C10 -11.4(3) . . . . ?
 C12 O5 C11 O4 4.4(4) . . . . ?
 C12 O5 C11 C8 -176.8(2) . . . . ?
 C13 O8 C14 O9 6.7(4) . . . . ?
 C13 O8 C14 C15 -172.1(2) . . . . ?
 C13 C6 C9 C8 -145.5(2) . . . . ?
 C13 C6 C9 C10 -24.4(3) . . . . ?
 C14 O8 C13 C6 -78.0(3) . . . . ?
 C14 C15 C16 C17 -166.7(2) . . . . ?
 C14 C15 C21 C18 -174.3(2) . . . . ?
 C14 C15 C21 C22 68.3(3) . . . . ?
 C14 C15 C21 C23 -58.1(3) . . . . ?
 C15 O10 C19 O11 177.1(3) . . . . ?
 C15 O10 C19 C18 -0.3(3) . . . . ?
 C15 C16 C17 C18 2.0(3) . . . . ?
 C16 C15 C21 C18 57.0(2) . . . . ?
 C16 C15 C21 C22 -60.5(3) . . . . ?
 C16 C15 C21 C23 173.2(2) . . . . ?
 C16 C17 C18 C19 -68.6(3) . . . . ?
 C16 C17 C18 C20 165.6(2) . . . . ?
 C16 C17 C18 C21 34.3(3) . . . . ?
 C17 C18 C19 O10 70.2(2) . . . . ?
 C17 C18 C19 O11 -106.8(3) . . . . ?
 C17 C18 C21 C15 -53.9(2) . . . . ?
 C17 C18 C21 C22 64.0(3) . . . . ?
 C17 C18 C21 C23 -170.1(2) . . . . ?
 C19 O10 C15 C14 159.9(2) . . . . ?
 C19 O10 C15 C16 -73.1(2) . . . . ?
 C19 O10 C15 C21 35.3(2) . . . . ?
 C19 C18 C21 C15 50.7(2) . . . . ?
 C19 C18 C21 C22 168.6(2) . . . . ?
 C19 C18 C21 C23 -65.5(3) . . . . ?
 C20 C18 C19 O10 -163.5(3) . . . . ?
 C20 C18 C19 O11 19.5(4) . . . . ?
 C20 C18 C21 C15 176.9(2) . . . . ?
 C20 C18 C21 C22 -65.3(3) . . . . ?
 C20 C18 C21 C23 60.7(4) . . . . ?
 C21 C15 C16 C17 -38.0(2) . . . . ?
 C21 C18 C19 O10 -34.5(3) . . . . ?
 C21 C18 C19 O11 148.5(3) . . . . ?

_smtbx_masks_special_details       ?
loop_
  _smtbx_masks_void_nr
  _smtbx_masks_void_average_x
  _smtbx_masks_void_average_y
  _smtbx_masks_void_average_z
  _smtbx_masks_void_volume
  _smtbx_masks_void_count_electrons
  _smtbx_masks_void_content
 1 -0.374 0.250 0.500 132.8 49.2 ?
 2 -0.392 0.750 0.000 132.8 49.2 ?

_smtbx_masks_void_probe_radius     1.2
_smtbx_masks_void_truncation_radius  1.2
_olex2_submission_special_instructions  'No special instructions were received'
