data_220191038_0m
_audit_creation_date               2019-10-15
_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. A71, 3-8.

Sheldrick, G.M. (2015). Acta Cryst. C71, 3-8.
;
_chemical_name_common              ?
_chemical_name_systematic          ?
_chemical_formula_moiety           'H2 O, C17 H24 O4'
_chemical_formula_sum              'C17 H26 O5'
_chemical_formula_weight           310.38
_chemical_absolute_configuration   rmad
_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                     9.8562(2)
_cell_length_b                     7.7464(2)
_cell_length_c                     10.3400(2)
_cell_angle_alpha                  90
_cell_angle_beta                   91.0550(10)
_cell_angle_gamma                  90
_cell_volume                       789.33(3)
_cell_formula_units_Z              2
_cell_measurement_reflns_used      8326
_cell_measurement_temperature      173(2)
_cell_measurement_theta_max        74.545
_cell_measurement_theta_min        4.277
_shelx_estimated_absorpt_T_max     0.913
_shelx_estimated_absorpt_T_min     0.866
_exptl_absorpt_coefficient_mu      0.777
_exptl_absorpt_correction_T_max    0.7538
_exptl_absorpt_correction_T_min    0.6369
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details    
 'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1477 before and 0.0568 after correction. The Ratio of minimum to maximum transmission is 0.8449. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details     ?
_exptl_crystal_colour              colourless
_exptl_crystal_colour_primary      colourless
_exptl_crystal_density_diffrn      1.306
_exptl_crystal_density_meas        ?
_exptl_crystal_density_method      ?
_exptl_crystal_description         block
_exptl_crystal_F_000               336
_exptl_crystal_size_max            0.19
_exptl_crystal_size_mid            0.15
_exptl_crystal_size_min            0.12
_exptl_transmission_factor_max     ?
_exptl_transmission_factor_min     ?
_diffrn_reflns_av_R_equivalents    0.0334
_diffrn_reflns_av_unetI/netI       0.0301
_diffrn_reflns_Laue_measured_fraction_full  0.997
_diffrn_reflns_Laue_measured_fraction_max  0.996
_diffrn_reflns_limit_h_max         12
_diffrn_reflns_limit_h_min         -12
_diffrn_reflns_limit_k_max         9
_diffrn_reflns_limit_k_min         -8
_diffrn_reflns_limit_l_max         12
_diffrn_reflns_limit_l_min         -12
_diffrn_reflns_number              10969
_diffrn_reflns_point_group_measured_fraction_full  0.961
_diffrn_reflns_point_group_measured_fraction_max  0.954
_diffrn_reflns_theta_full          67.679
_diffrn_reflns_theta_max           74.643
_diffrn_reflns_theta_min           4.276
_diffrn_ambient_temperature        173.0
_diffrn_detector_area_resol_mean   ?
_diffrn_measured_fraction_theta_full  0.997
_diffrn_measured_fraction_theta_max  0.996
_diffrn_measurement_device_type    'D8 VENTURE'
_diffrn_measurement_method         'φ and ω scans'
_diffrn_radiation_type             CuK\a
_diffrn_radiation_wavelength       1.54178
_diffrn_source                     ?
_diffrn_standards_number           0
_reflns_Friedel_coverage           0.778
_reflns_Friedel_fraction_full      0.919
_reflns_Friedel_fraction_max       0.904
_reflns_number_gt                  2979
_reflns_number_total               3087
_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 (Sheldrick, 2015)'
_refine_diff_density_max           0.225
_refine_diff_density_min           -0.134
_refine_diff_density_rms           0.033
_refine_ls_abs_structure_details
;
 Flack x determined using 1257 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack     0.05(8)
_refine_ls_extinction_coef         .
_refine_ls_extinction_method       none
_refine_ls_goodness_of_fit_ref     1.058
_refine_ls_hydrogen_treatment      mixed
_refine_ls_matrix_type             full
_refine_ls_number_parameters       211
_refine_ls_number_reflns           3087
_refine_ls_number_restraints       1
_refine_ls_R_factor_all            0.0316
_refine_ls_R_factor_gt             0.0299
_refine_ls_restrained_S_all        1.057
_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)+(0.0445P)²+0.0802P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme        calc
_refine_ls_wR_factor_gt            0.0760
_refine_ls_wR_factor_ref           0.0779
_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) groups
2.a Ternary CH refined with riding coordinates:
 C5(H5), C7(H7), C9(H9)
2.b Secondary CH2 refined with riding coordinates:
 C13(H13A,H13B), C8(H8A,H8B), C14(H14A,H14B), C3(H3A,H3B), C2(H2A,H2B), C1(H1A,
 H1B)
2.c Aromatic/amide H refined with riding coordinates:
 C11(H11)
2.d Idealised Me refined as rotating group:
 C15(H15A,H15B,H15C), C16(H16A,H16B,H16C)
2.e Idealised tetrahedral OH refined as rotating group:
 O1(H1), O4(H4)
;
_atom_sites_solution_hydrogens     mixed
_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
 O3 O 0.10889(15) 0.5380(2) 0.05716(14) 0.0273(3) Uani 1 1 d . . . . .
 O5 O 0.94435(15) 0.69846(19) 0.86505(14) 0.0279(3) Uani 1 1 d . . . . .
 O2 O 0.36561(14) 0.6183(2) 0.25985(14) 0.0316(4) Uani 1 1 d . . . . .
 O1 O 0.38159(14) 0.5073(2) 0.06222(13) 0.0303(3) Uani 1 1 d . . . . .
 H1 H 0.297734 0.526700 0.060776 0.045 Uiso 1 1 calc GR . . . .
 O4 O 0.96492(17) 0.3601(2) 0.83647(15) 0.0347(4) Uani 1 1 d . . . . .
 H4 H 0.940115 0.260250 0.857068 0.052 Uiso 1 1 calc GR . . . .
 C12 C 0.74284(17) 0.6724(2) 0.57492(17) 0.0195(4) Uani 1 1 d . . . . .
 C10 C 0.87718(18) 0.6340(3) 0.77604(18) 0.0218(4) Uani 1 1 d . . . . .
 C13 C 0.6536(2) 0.7867(2) 0.49191(19) 0.0245(4) Uani 1 1 d . . . . .
 H13A H 0.685525 0.907297 0.501440 0.029 Uiso 1 1 calc R . . . .
 H13B H 0.560079 0.781389 0.524894 0.029 Uiso 1 1 calc R . . . .
 C4 C 0.75462(17) 0.4493(2) 0.39366(17) 0.0181(4) Uani 1 1 d . . . . .
 C8 C 0.8624(2) 0.3909(3) 0.62034(18) 0.0227(4) Uani 1 1 d . . . . .
 H8A H 0.851070 0.264393 0.612200 0.027 Uiso 1 1 calc R . . . .
 H8B H 0.951287 0.422101 0.583882 0.027 Uiso 1 1 calc R . . . .
 C11 C 0.80492(18) 0.7395(3) 0.68073(18) 0.0221(4) Uani 1 1 d . . . . .
 H11 H 0.801395 0.860814 0.693689 0.027 Uiso 1 1 calc R . . . .
 C14 C 0.64949(19) 0.7414(2) 0.34856(18) 0.0230(4) Uani 1 1 d . . . . .
 H14A H 0.735206 0.777428 0.308057 0.028 Uiso 1 1 calc R . . . .
 H14B H 0.573675 0.803298 0.304882 0.028 Uiso 1 1 calc R . . . .
 C5 C 0.63026(17) 0.5466(2) 0.33291(16) 0.0177(3) Uani 1 1 d . . . . .
 H5 H 0.552641 0.517251 0.389839 0.021 Uiso 1 1 calc R . . . .
 C15 C 0.89050(18) 0.5147(3) 0.34307(18) 0.0255(4) Uani 1 1 d . . . . .
 H15A H 0.887810 0.514600 0.248280 0.038 Uiso 1 1 calc GR . . . .
 H15B H 0.963755 0.438900 0.374107 0.038 Uiso 1 1 calc GR . . . .
 H15C H 0.906809 0.632364 0.374480 0.038 Uiso 1 1 calc GR . . . .
 C17 C 0.43346(18) 0.5496(3) 0.17764(17) 0.0222(4) Uani 1 1 d . . . . .
 C7 C 0.74887(18) 0.4820(2) 0.54283(17) 0.0186(4) Uani 1 1 d . . . . .
 H7 H 0.661535 0.430862 0.572219 0.022 Uiso 1 1 calc R . . . .
 C6 C 0.58198(18) 0.4931(2) 0.19439(17) 0.0210(4) Uani 1 1 d . . . . .
 C3 C 0.7421(2) 0.2542(2) 0.36826(19) 0.0237(4) Uani 1 1 d . . . . .
 H3A H 0.827442 0.196739 0.396226 0.028 Uiso 1 1 calc R . . . .
 H3B H 0.667880 0.206991 0.420963 0.028 Uiso 1 1 calc R . . . .
 C16 C 0.6644(2) 0.5733(3) 0.08420(19) 0.0299(4) Uani 1 1 d . . . . .
 H16A H 0.666097 0.699097 0.093820 0.045 Uiso 1 1 calc GR . . . .
 H16B H 0.622160 0.543006 0.000712 0.045 Uiso 1 1 calc GR . . . .
 H16C H 0.757440 0.528570 0.088024 0.045 Uiso 1 1 calc GR . . . .
 C9 C 0.8609(2) 0.4410(3) 0.76316(18) 0.0239(4) Uani 1 1 d . . . . .
 H9 H 0.771412 0.407100 0.799380 0.029 Uiso 1 1 calc R . . . .
 C2 C 0.7136(2) 0.2124(3) 0.22660(19) 0.0278(4) Uani 1 1 d . . . . .
 H2A H 0.708724 0.085664 0.214963 0.033 Uiso 1 1 calc R . . . .
 H2B H 0.788445 0.256700 0.173344 0.033 Uiso 1 1 calc R . . . .
 C1 C 0.5797(2) 0.2944(3) 0.18194(19) 0.0264(4) Uani 1 1 d . . . . .
 H1A H 0.505120 0.247716 0.234384 0.032 Uiso 1 1 calc R . . . .
 H1B H 0.561218 0.262799 0.090536 0.032 Uiso 1 1 calc R . . . .
 H3C H 0.063(3) 0.553(5) -0.012(3) 0.058(9) Uiso 1 1 d . . . . .
 H3D H 0.090(3) 0.445(5) 0.084(3) 0.049(9) Uiso 1 1 d . . . . .


_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
 O3 H3C 0.84(4) . ?
 O3 H3D 0.79(4) . ?
 O5 C10 1.230(2) . ?
 O2 C17 1.214(2) . ?
 O1 H1 0.8400 . ?
 O1 C17 1.331(2) . ?
 O4 H4 0.8400 . ?
 O4 C9 1.410(2) . ?
 C12 C13 1.505(2) . ?
 C12 C11 1.348(3) . ?
 C12 C7 1.513(3) . ?
 C10 C11 1.456(3) . ?
 C10 C9 1.509(3) . ?
 C13 H13A 0.9900 . ?
 C13 H13B 0.9900 . ?
 C13 C14 1.523(3) . ?
 C4 C5 1.561(2) . ?
 C4 C15 1.533(3) . ?
 C4 C7 1.565(2) . ?
 C4 C3 1.539(3) . ?
 C8 H8A 0.9900 . ?
 C8 H8B 0.9900 . ?
 C8 C7 1.536(2) . ?
 C8 C9 1.527(3) . ?
 C11 H11 0.9500 . ?
 C14 H14A 0.9900 . ?
 C14 H14B 0.9900 . ?
 C14 C5 1.529(3) . ?
 C5 H5 1.0000 . ?
 C5 C6 1.557(2) . ?
 C15 H15A 0.9800 . ?
 C15 H15B 0.9800 . ?
 C15 H15C 0.9800 . ?
 C17 C6 1.535(3) . ?
 C7 H7 1.0000 . ?
 C6 C16 1.542(3) . ?
 C6 C1 1.545(3) . ?
 C3 H3A 0.9900 . ?
 C3 H3B 0.9900 . ?
 C3 C2 1.521(3) . ?
 C16 H16A 0.9800 . ?
 C16 H16B 0.9800 . ?
 C16 H16C 0.9800 . ?
 C9 H9 1.0000 . ?
 C2 H2A 0.9900 . ?
 C2 H2B 0.9900 . ?
 C2 C1 1.529(3) . ?
 C1 H1A 0.9900 . ?
 C1 H1B 0.9900 . ?

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
 H3C O3 H3D 107(3) . . ?
 C17 O1 H1 109.5 . . ?
 C9 O4 H4 109.5 . . ?
 C13 C12 C7 118.23(15) . . ?
 C11 C12 C13 119.21(17) . . ?
 C11 C12 C7 122.32(17) . . ?
 O5 C10 C11 121.89(18) . . ?
 O5 C10 C9 121.54(18) . . ?
 C11 C10 C9 116.52(16) . . ?
 C12 C13 H13A 108.5 . . ?
 C12 C13 H13B 108.5 . . ?
 C12 C13 C14 115.12(16) . . ?
 H13A C13 H13B 107.5 . . ?
 C14 C13 H13A 108.5 . . ?
 C14 C13 H13B 108.5 . . ?
 C5 C4 C7 106.01(13) . . ?
 C15 C4 C5 112.81(15) . . ?
 C15 C4 C7 109.30(14) . . ?
 C15 C4 C3 109.53(16) . . ?
 C3 C4 C5 110.23(14) . . ?
 C3 C4 C7 108.85(15) . . ?
 H8A C8 H8B 108.0 . . ?
 C7 C8 H8A 109.3 . . ?
 C7 C8 H8B 109.3 . . ?
 C9 C8 H8A 109.3 . . ?
 C9 C8 H8B 109.3 . . ?
 C9 C8 C7 111.61(16) . . ?
 C12 C11 C10 122.83(18) . . ?
 C12 C11 H11 118.6 . . ?
 C10 C11 H11 118.6 . . ?
 C13 C14 H14A 109.8 . . ?
 C13 C14 H14B 109.8 . . ?
 C13 C14 C5 109.36(15) . . ?
 H14A C14 H14B 108.2 . . ?
 C5 C14 H14A 109.8 . . ?
 C5 C14 H14B 109.8 . . ?
 C4 C5 H5 104.9 . . ?
 C14 C5 C4 109.82(14) . . ?
 C14 C5 H5 104.9 . . ?
 C14 C5 C6 113.27(15) . . ?
 C6 C5 C4 117.78(15) . . ?
 C6 C5 H5 104.9 . . ?
 C4 C15 H15A 109.5 . . ?
 C4 C15 H15B 109.5 . . ?
 C4 C15 H15C 109.5 . . ?
 H15A C15 H15B 109.5 . . ?
 H15A C15 H15C 109.5 . . ?
 H15B C15 H15C 109.5 . . ?
 O2 C17 O1 121.91(17) . . ?
 O2 C17 C6 125.63(16) . . ?
 O1 C17 C6 112.39(16) . . ?
 C12 C7 C4 112.10(14) . . ?
 C12 C7 C8 111.38(14) . . ?
 C12 C7 H7 106.4 . . ?
 C4 C7 H7 106.4 . . ?
 C8 C7 C4 113.61(15) . . ?
 C8 C7 H7 106.4 . . ?
 C17 C6 C5 107.62(15) . . ?
 C17 C6 C16 108.45(15) . . ?
 C17 C6 C1 105.21(15) . . ?
 C16 C6 C5 114.60(15) . . ?
 C16 C6 C1 110.27(17) . . ?
 C1 C6 C5 110.21(15) . . ?
 C4 C3 H3A 109.0 . . ?
 C4 C3 H3B 109.0 . . ?
 H3A C3 H3B 107.8 . . ?
 C2 C3 C4 112.71(16) . . ?
 C2 C3 H3A 109.0 . . ?
 C2 C3 H3B 109.0 . . ?
 C6 C16 H16A 109.5 . . ?
 C6 C16 H16B 109.5 . . ?
 C6 C16 H16C 109.5 . . ?
 H16A C16 H16B 109.5 . . ?
 H16A C16 H16C 109.5 . . ?
 H16B C16 H16C 109.5 . . ?
 O4 C9 C10 108.52(15) . . ?
 O4 C9 C8 112.79(17) . . ?
 O4 C9 H9 108.6 . . ?
 C10 C9 C8 109.51(16) . . ?
 C10 C9 H9 108.6 . . ?
 C8 C9 H9 108.6 . . ?
 C3 C2 H2A 109.6 . . ?
 C3 C2 H2B 109.6 . . ?
 C3 C2 C1 110.21(16) . . ?
 H2A C2 H2B 108.1 . . ?
 C1 C2 H2A 109.6 . . ?
 C1 C2 H2B 109.6 . . ?
 C6 C1 H1A 109.2 . . ?
 C6 C1 H1B 109.2 . . ?
 C2 C1 C6 112.21(16) . . ?
 C2 C1 H1A 109.2 . . ?
 C2 C1 H1B 109.2 . . ?
 H1A C1 H1B 107.9 . . ?


_olex2_submission_special_instructions  'No special instructions were received'
