data_dmo
_audit_creation_date               2018-06-29
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_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. C71, 3-8.
;
_chemical_name_common              ?
_chemical_name_systematic          ?
_chemical_formula_moiety           'C30 H32 O6, 2(H2 O)'
_chemical_formula_sum              'C30 H36 O8'
_chemical_formula_weight           524.59
_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' 0.0033 0.0016 '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' 0.0106 0.0060 '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             14
_space_group_name_H-M_alt          'P 1 21/c 1'
_space_group_name_Hall             '-P 2ybc'
loop_
  _space_group_symop_operation_xyz
 'x, y, z'
 '-x, y+1/2, -z+1/2'
 '-x, -y, -z'
 'x, -y-1/2, z-1/2'

_cell_length_a                     14.4791(17)
_cell_length_b                     13.0125(13)
_cell_length_c                     16.8365(17)
_cell_angle_alpha                  90
_cell_angle_beta                   109.243(4)
_cell_angle_gamma                  90
_cell_volume                       2994.9(6)
_cell_formula_units_Z              4
_cell_measurement_reflns_used      8936
_cell_measurement_temperature      196(2)
_cell_measurement_theta_max        28.26
_cell_measurement_theta_min        2.95
_shelx_estimated_absorpt_T_max     ?
_shelx_estimated_absorpt_T_min     ?
_exptl_absorpt_coefficient_mu      0.084
_exptl_absorpt_correction_T_max    0.992
_exptl_absorpt_correction_T_min    0.980
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details     ?
_exptl_absorpt_special_details     ?
_exptl_crystal_colour              ad
_exptl_crystal_density_diffrn      1.163
_exptl_crystal_density_meas        ?
_exptl_crystal_density_method      'not measured'
_exptl_crystal_description         block
_exptl_crystal_F_000               1120
_exptl_crystal_size_max            0.4
_exptl_crystal_size_mid            0.2
_exptl_crystal_size_min            0.1
_exptl_transmission_factor_max     ?
_exptl_transmission_factor_min     ?
_diffrn_reflns_av_R_equivalents    0.0682
_diffrn_reflns_av_unetI/netI       0.0572
_diffrn_reflns_Laue_measured_fraction_full  0.981
_diffrn_reflns_Laue_measured_fraction_max  0.972
_diffrn_reflns_limit_h_max         15
_diffrn_reflns_limit_h_min         -18
_diffrn_reflns_limit_k_max         16
_diffrn_reflns_limit_k_min         -16
_diffrn_reflns_limit_l_max         21
_diffrn_reflns_limit_l_min         -21
_diffrn_reflns_number              29456
_diffrn_reflns_point_group_measured_fraction_full  0.981
_diffrn_reflns_point_group_measured_fraction_max  0.972
_diffrn_reflns_theta_full          25.242
_diffrn_reflns_theta_max           26.499
_diffrn_reflns_theta_min           2.953
_diffrn_ambient_temperature        196.4
_diffrn_detector_area_resol_mean   16.0971
_diffrn_measured_fraction_theta_full  0.981
_diffrn_measured_fraction_theta_max  0.972
_diffrn_measurement_device_type    'Bruker APEX-II CCD'
_diffrn_measurement_method         'φ and ω scans'
_diffrn_radiation_type             MoK\a
_diffrn_radiation_wavelength       0.71073
_diffrn_source                     ?
_diffrn_standards_number           0
_reflns_Friedel_coverage           0.000
_reflns_Friedel_fraction_full      .
_reflns_Friedel_fraction_max       .
_reflns_number_gt                  3544
_reflns_number_total               6031
_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 V8.38A (?, 2016)'
_computing_data_collection         ?
_computing_data_reduction          'SAINT V8.38A (?, 2016)'
_computing_molecular_graphics      'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material    'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement    'ShelXL (Sheldrick, 2015)'
_computing_structure_solution      'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max           0.654
_refine_diff_density_min           -0.416
_refine_diff_density_rms           0.111
_refine_ls_extinction_coef         .
_refine_ls_extinction_method       none
_refine_ls_goodness_of_fit_ref     1.160
_refine_ls_hydrogen_treatment      constr
_refine_ls_matrix_type             full
_refine_ls_number_parameters       355
_refine_ls_number_reflns           6031
_refine_ls_number_restraints       0
_refine_ls_R_factor_all            0.1009
_refine_ls_R_factor_gt             0.0717
_refine_ls_restrained_S_all        1.160
_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)+(0.2000P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme        calc
_refine_ls_wR_factor_gt            0.1424
_refine_ls_wR_factor_ref           0.1824
_refine_special_details            ?
_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,H) groups
2. Restrained distances
 O17-O18
 2.5 with sigma of 0.02
3.a Free rotating group:
 O17(H17A,H17B), O18(H18A,H18B)
3.b Secondary CH2 refined with riding coordinates:
 C12(H12A,H12B), C11(H11A,H11B)
3.c Aromatic/amide H refined with riding coordinates:
 C9(H9), C8(H8), C17(H17), C5(H5), C15(H15), C3(H3), C1(H1), C26(H26), C2(H2),
 C24(H24)
3.d Idealised Me refined as rotating group:
 C20(H20A,H20B,H20C), C21(H21A,H21B,H21C), C28(H28A,H28B,H28C), C19(H19A,H19B,
 H19C), C29(H29A,H29B,H29C), C30(H30A,H30B,H30C)
;
_atom_sites_solution_hydrogens     mixed
_atom_sites_solution_primary       ?
_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
 O12 O 0.8478(4) 0.6087(4) 0.4991(3) 0.0679(15) Uani 1 1 d . . . . .
 O13 O 0.9139(4) 0.2667(4) 0.4589(3) 0.0711(15) Uani 1 1 d . . . . .
 O11 O 0.8669(4) 0.3723(4) 0.7188(3) 0.0741(16) Uani 1 1 d . . . . .
 O14 O 0.4596(4) 0.2509(4) 0.1371(4) 0.0776(16) Uani 1 1 d . . . . .
 O15 O 0.3987(4) 0.5997(4) 0.1425(5) 0.095(2) Uani 1 1 d . . . . .
 C13 C 0.8814(4) 0.4374(5) 0.4809(3) 0.0433(14) Uani 1 1 d . . . . .
 C4 C 0.7000(5) 0.4805(5) 0.1717(3) 0.0464(15) Uani 1 1 d . . . . .
 C9 C 0.6161(4) 0.4345(5) 0.2670(3) 0.0472(15) Uani 1 1 d . . . . .
 H9 H 0.557569 0.417746 0.277996 0.057 Uiso 1 1 calc R . . . .
 C6 C 0.7913(4) 0.4847(5) 0.2400(3) 0.0433(15) Uani 1 1 d . . . . .
 C8 C 0.7059(4) 0.4387(5) 0.3357(3) 0.0461(15) Uani 1 1 d . . . . .
 H8 H 0.705617 0.424520 0.390933 0.055 Uiso 1 1 calc R . . . .
 C14 C 0.8953(5) 0.3384(5) 0.5112(3) 0.0482(16) Uani 1 1 d . . . . .
 C7 C 0.7917(4) 0.4626(5) 0.3237(3) 0.0418(14) Uani 1 1 d . . . . .
 C12 C 0.8881(5) 0.4652(5) 0.3949(4) 0.0509(16) Uani 1 1 d . . . . .
 H12A H 0.916134 0.535062 0.398144 0.061 Uiso 1 1 calc R . . . .
 H12B H 0.933807 0.416932 0.381694 0.061 Uiso 1 1 calc R . . . .
 C10 C 0.6116(4) 0.4534(5) 0.1872(3) 0.0450(15) Uani 1 1 d . . . . .
 C22 C 0.4265(5) 0.4255(5) 0.1382(4) 0.0503(16) Uani 1 1 d . . . . .
 C18 C 0.8630(4) 0.5122(5) 0.5334(4) 0.0478(15) Uani 1 1 d . . . . .
 C16 C 0.8722(5) 0.3881(5) 0.6391(4) 0.0526(17) Uani 1 1 d . . . . .
 C17 C 0.8596(5) 0.4885(5) 0.6126(4) 0.0510(16) Uani 1 1 d . . . . .
 H17 H 0.848813 0.540804 0.647972 0.061 Uiso 1 1 calc R . . . .
 O16 O 0.1769(5) 0.3684(6) 0.2033(5) 0.106(2) Uani 1 1 d . . . . .
 C5 C 0.8763(5) 0.5103(6) 0.2226(4) 0.0576(18) Uani 1 1 d . . . . .
 H5 H 0.936615 0.514364 0.267524 0.069 Uiso 1 1 calc R . . . .
 C23 C 0.3991(5) 0.3248(6) 0.1479(4) 0.0574(18) Uani 1 1 d . . . . .
 C11 C 0.5158(5) 0.4477(6) 0.1142(4) 0.0523(16) Uani 1 1 d . . . . .
 H11A H 0.505834 0.513869 0.083517 0.063 Uiso 1 1 calc R . . . .
 H11B H 0.521920 0.393545 0.074909 0.063 Uiso 1 1 calc R . . . .
 C15 C 0.8912(5) 0.3119(6) 0.5908(4) 0.0543(17) Uani 1 1 d . . . . .
 H15 H 0.901169 0.242979 0.610524 0.065 Uiso 1 1 calc R . . . .
 C27 C 0.3673(5) 0.5034(6) 0.1514(5) 0.0603(19) Uani 1 1 d . . . . .
 C3 C 0.7031(5) 0.5018(6) 0.0895(4) 0.063(2) Uani 1 1 d . . . . .
 H3 H 0.644210 0.498582 0.042943 0.075 Uiso 1 1 calc R . . . .
 C1 C 0.8749(6) 0.5297(7) 0.1420(4) 0.069(2) Uani 1 1 d . . . . .
 H1 H 0.933953 0.545300 0.131548 0.083 Uiso 1 1 calc R . . . .
 C26 C 0.2844(6) 0.4830(7) 0.1744(5) 0.071(2) Uani 1 1 d . . . . .
 H26 H 0.245693 0.537436 0.184089 0.085 Uiso 1 1 calc R . . . .
 C2 C 0.7873(6) 0.5265(6) 0.0759(4) 0.070(2) Uani 1 1 d . . . . .
 H2 H 0.786377 0.541752 0.020477 0.084 Uiso 1 1 calc R . . . .
 C24 C 0.3149(6) 0.3029(6) 0.1697(5) 0.066(2) Uani 1 1 d . . . . .
 H24 H 0.296559 0.233813 0.175268 0.079 Uiso 1 1 calc R . . . .
 C25 C 0.2608(6) 0.3820(7) 0.1825(5) 0.069(2) Uani 1 1 d . . . . .
 C20 C 0.8648(8) 0.2683(8) 0.7437(5) 0.093(3) Uani 1 1 d . . . . .
 H20A H 0.813838 0.231064 0.700131 0.139 Uiso 1 1 calc GR . . . .
 H20B H 0.850654 0.265669 0.796740 0.139 Uiso 1 1 calc GR . . . .
 H20C H 0.928464 0.236268 0.751509 0.139 Uiso 1 1 calc GR . . . .
 C21 C 0.8322(8) 0.6902(7) 0.5477(6) 0.089(3) Uani 1 1 d . . . . .
 H21A H 0.821611 0.753775 0.514781 0.134 Uiso 1 1 calc GR . . . .
 H21B H 0.889595 0.698062 0.598344 0.134 Uiso 1 1 calc GR . . . .
 H21C H 0.774523 0.675557 0.564033 0.134 Uiso 1 1 calc GR . . . .
 C28 C 0.4384(9) 0.1466(7) 0.1533(7) 0.103(3) Uani 1 1 d . . . . .
 H28A H 0.377729 0.124426 0.110313 0.154 Uiso 1 1 calc GR . . . .
 H28B H 0.430864 0.142359 0.208928 0.154 Uiso 1 1 calc GR . . . .
 H28C H 0.492307 0.101984 0.151696 0.154 Uiso 1 1 calc GR . . . .
 C19 C 0.9421(10) 0.1661(7) 0.4891(6) 0.111(4) Uani 1 1 d . . . . .
 H19A H 0.942571 0.121726 0.442192 0.166 Uiso 1 1 calc GR . . . .
 H19B H 0.895472 0.138937 0.514840 0.166 Uiso 1 1 calc GR . . . .
 H19C H 1.007639 0.167886 0.531139 0.166 Uiso 1 1 calc GR . . . .
 C29 C 0.1531(9) 0.2650(10) 0.2188(8) 0.119(4) Uani 1 1 d . . . . .
 H29A H 0.128433 0.227772 0.165329 0.179 Uiso 1 1 calc GR . . . .
 H29B H 0.102687 0.265953 0.245935 0.179 Uiso 1 1 calc GR . . . .
 H29C H 0.211732 0.230555 0.255691 0.179 Uiso 1 1 calc GR . . . .
 C30 C 0.3456(9) 0.6831(9) 0.1588(12) 0.167(7) Uani 1 1 d . . . . .
 H30A H 0.280515 0.685339 0.115937 0.250 Uiso 1 1 calc GR . . . .
 H30B H 0.380328 0.747340 0.157299 0.250 Uiso 1 1 calc GR . . . .
 H30C H 0.338825 0.674769 0.214480 0.250 Uiso 1 1 calc GR . . . .
 O17 O 0.5768(17) 0.414(3) 0.5252(15) 0.43(2) Uani 1 1 d D . . . .
 H17A H 0.573724 0.349810 0.538709 0.639 Uiso 1 1 d G . . . .
 H17B H 0.546613 0.447115 0.554196 0.639 Uiso 1 1 d G . . . .
 O18 O 0.558(2) 0.592(3) 0.5686(16) 0.51(3) Uani 1 1 d D . . . .
 H18A H 0.523660 0.647057 0.550695 0.770 Uiso 1 1 d G . . . .
 H18B H 0.617862 0.609853 0.576116 0.770 Uiso 1 1 d G . . . .


_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
 O12 C18 1.370(8) . ?
 O12 C21 1.402(10) . ?
 O13 C14 1.369(8) . ?
 O13 C19 1.415(10) . ?
 O11 C16 1.384(8) . ?
 O11 C20 1.421(11) . ?
 O14 C23 1.352(9) . ?
 O14 C28 1.436(10) . ?
 O15 C27 1.359(9) . ?
 O15 C30 1.409(13) . ?
 C13 C14 1.375(9) . ?
 C13 C12 1.525(8) . ?
 C13 C18 1.399(9) . ?
 C4 C6 1.438(8) . ?
 C4 C10 1.432(9) . ?
 C4 C3 1.427(8) . ?
 C9 C8 1.428(8) . ?
 C9 C10 1.347(8) . ?
 C6 C7 1.436(8) . ?
 C6 C5 1.397(9) . ?
 C8 C7 1.358(8) . ?
 C14 C15 1.406(8) . ?
 C7 C12 1.511(8) . ?
 C10 C11 1.521(8) . ?
 C22 C23 1.394(10) . ?
 C22 C11 1.504(9) . ?
 C22 C27 1.392(10) . ?
 C18 C17 1.385(9) . ?
 C16 C17 1.373(9) . ?
 C16 C15 1.367(9) . ?
 O16 C25 1.381(10) . ?
 O16 C29 1.435(13) . ?
 C5 C1 1.373(9) . ?
 C23 C24 1.414(10) . ?
 C27 C26 1.402(11) . ?
 C3 C2 1.351(10) . ?
 C1 C2 1.385(10) . ?
 C26 C25 1.376(11) . ?
 C24 C25 1.354(11) . ?

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
 C18 O12 C21 118.8(6) . . ?
 C14 O13 C19 119.6(6) . . ?
 C16 O11 C20 116.2(6) . . ?
 C23 O14 C28 117.3(6) . . ?
 C27 O15 C30 117.7(8) . . ?
 C14 C13 C12 121.8(5) . . ?
 C14 C13 C18 116.9(5) . . ?
 C18 C13 C12 121.3(6) . . ?
 C10 C4 C6 120.3(5) . . ?
 C3 C4 C6 117.0(6) . . ?
 C3 C4 C10 122.7(5) . . ?
 C10 C9 C8 122.1(6) . . ?
 C7 C6 C4 118.9(5) . . ?
 C5 C6 C4 118.8(5) . . ?
 C5 C6 C7 122.3(5) . . ?
 C7 C8 C9 121.5(5) . . ?
 O13 C14 C13 115.8(5) . . ?
 O13 C14 C15 121.7(6) . . ?
 C13 C14 C15 122.5(6) . . ?
 C6 C7 C12 118.6(5) . . ?
 C8 C7 C6 118.9(5) . . ?
 C8 C7 C12 122.5(5) . . ?
 C7 C12 C13 114.7(5) . . ?
 C4 C10 C11 119.8(5) . . ?
 C9 C10 C4 118.3(5) . . ?
 C9 C10 C11 121.9(5) . . ?
 C23 C22 C11 121.0(6) . . ?
 C27 C22 C23 116.8(6) . . ?
 C27 C22 C11 122.2(6) . . ?
 O12 C18 C13 114.1(5) . . ?
 O12 C18 C17 123.9(6) . . ?
 C17 C18 C13 122.0(6) . . ?
 C17 C16 O11 114.4(6) . . ?
 C15 C16 O11 123.7(6) . . ?
 C15 C16 C17 122.0(6) . . ?
 C16 C17 C18 118.7(6) . . ?
 C25 O16 C29 116.8(8) . . ?
 C1 C5 C6 121.6(6) . . ?
 O14 C23 C22 115.5(6) . . ?
 O14 C23 C24 122.9(7) . . ?
 C22 C23 C24 121.5(7) . . ?
 C22 C11 C10 115.3(5) . . ?
 C16 C15 C14 118.0(6) . . ?
 O15 C27 C22 114.0(7) . . ?
 O15 C27 C26 123.6(7) . . ?
 C22 C27 C26 122.4(7) . . ?
 C2 C3 C4 121.9(6) . . ?
 C5 C1 C2 120.0(7) . . ?
 C25 C26 C27 118.1(7) . . ?
 C3 C2 C1 120.7(6) . . ?
 C25 C24 C23 118.8(7) . . ?
 C26 C25 O16 114.6(7) . . ?
 C24 C25 O16 123.1(8) . . ?
 C24 C25 C26 122.3(7) . . ?