# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2017

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_exp_1173
_database_code_depnum_ccdc_archive 'CCDC 1516458'
_audit_update_record             
;
2016-11-11 deposited with the CCDC.
2017-01-09 downloaded from the CCDC.
;
_audit_creation_date             2013-03-12
_audit_creation_method           
;
  Olex2 1.1
  (compiled 2011.02.15 svn.r1672, GUI svn.r3494)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C15 H24 O4'
_chemical_formula_sum            'C15 H24 O4'
_chemical_formula_weight         268.34
_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'

_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_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x+1/2, -y, z+1/2'
3 'x+1/2, -y+1/2, -z'
4 '-x, y+1/2, -z+1/2'

_cell_length_a                   6.96010(16)
_cell_length_b                   7.10939(15)
_cell_length_c                   27.6935(7)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1370.33(5)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2729
_cell_measurement_temperature    101.5
_cell_measurement_theta_max      71.7478
_cell_measurement_theta_min      4.7865
_exptl_absorpt_coefficient_mu    0.753
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.70322
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.301
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       ?
_exptl_crystal_F_000             584
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.15
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0170
_diffrn_reflns_av_unetI/netI     0.0260
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_number            4377
_diffrn_reflns_theta_full        71.89
_diffrn_reflns_theta_max         71.89
_diffrn_reflns_theta_min         6.39
_diffrn_ambient_temperature      101.5
_diffrn_detector_area_resol_mean 16.0971
_diffrn_measured_fraction_theta_full 0.982
_diffrn_measured_fraction_theta_max 0.982
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega   26.00   52.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -        0.0000   37.0000  -90.0000 26

#__ type_ start__ end____ width___ exp.time_
  2 omega -106.00  -48.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -42.5000  -77.0000   30.0000 58

#__ type_ start__ end____ width___ exp.time_
  3 omega -107.00  -24.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -42.5000  154.0000  121.0000 83

#__ type_ start__ end____ width___ exp.time_
  4 omega  -40.00   28.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -42.5000   37.0000  -60.0000 68

#__ type_ start__ end____ width___ exp.time_
  5 omega  -43.00  -18.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -42.5000  -77.0000   30.0000 25

#__ type_ start__ end____ width___ exp.time_
  6 omega   91.00  177.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   45.0000  120.0000 86

#__ type_ start__ end____ width___ exp.time_
  7 omega  145.00  178.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  137.0000 -159.0000 33

#__ type_ start__ end____ width___ exp.time_
  8 omega  115.00  174.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  111.0000  150.0000 59

#__ type_ start__ end____ width___ exp.time_
  9 omega   89.00  167.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  154.0000   98.0000 78

#__ type_ start__ end____ width___ exp.time_
 10 omega   89.00  159.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   45.0000 -120.0000 70

#__ type_ start__ end____ width___ exp.time_
 11 omega   56.00   97.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -45.0000  -30.0000 41

#__ type_ start__ end____ width___ exp.time_
 12 omega   95.00  120.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   45.0000 -150.0000 25

#__ type_ start__ end____ width___ exp.time_
 13 omega   41.00   98.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -45.0000   30.0000 57
;
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.2171422000
_diffrn_orient_matrix_UB_12      0.0013123000
_diffrn_orient_matrix_UB_13      -0.0108951000
_diffrn_orient_matrix_UB_21      -0.0431817000
_diffrn_orient_matrix_UB_22      0.0259581000
_diffrn_orient_matrix_UB_23      -0.0541242000
_diffrn_orient_matrix_UB_31      0.0036822000
_diffrn_orient_matrix_UB_32      0.2151514000
_diffrn_orient_matrix_UB_33      0.0066061000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.5418
_diffrn_source                   'Enhance (Cu) X-ray Source'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                2568
_reflns_number_total             2610
_reflns_odcompleteness_completeness 99.73
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_molecular_graphics    
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material  
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    
'A short history of SHELX (Sheldrick, 2007)/Bruker'
_refine_diff_density_max         0.299
_refine_diff_density_min         -0.289
_refine_diff_density_rms         0.059
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.01(16)
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.090
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     178
_refine_ls_number_reflns         2610
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0386
_refine_ls_R_factor_gt           0.0381
_refine_ls_restrained_S_all      1.090
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0677P)²+0.2080P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0973
_refine_ls_wR_factor_ref         0.0980
_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O -0.98311(15) -0.33192(14) -0.17154(3) 0.0111(2) Uani 1 1 d . . .
O3 O -0.34742(15) -0.18575(17) -0.13847(4) 0.0170(2) Uani 1 1 d . . .
H3 H -0.2502 -0.2435 -0.1486 0.025 Uiso 1 1 calc R . .
O2 O -0.80906(16) -0.14465(15) -0.27196(3) 0.0141(2) Uani 1 1 d . . .
H2 H -0.8264 -0.0286 -0.2682 0.021 Uiso 1 1 calc R . .
O4 O -0.87250(15) 0.14262(15) -0.20866(4) 0.0141(2) Uani 1 1 d . . .
H4 H -0.9468 0.2329 -0.2145 0.021 Uiso 1 1 calc R . .
C6 C -0.7796(2) -0.3259(2) -0.10310(5) 0.0121(3) Uani 1 1 d . . .
C5 C -0.6989(2) -0.1775(2) -0.13956(5) 0.0110(3) Uani 1 1 d . . .
C2 C -0.7324(2) -0.2230(2) -0.22854(5) 0.0114(3) Uani 1 1 d . . .
H2A H -0.7315 -0.3627 -0.2327 0.014 Uiso 1 1 calc R . .
C12 C -0.9793(2) -0.0092(2) -0.18809(5) 0.0123(3) Uani 1 1 d . . .
H12A H -1.0886 -0.0414 -0.2094 0.015 Uiso 1 1 calc R . .
H12B H -1.0314 0.0293 -0.1563 0.015 Uiso 1 1 calc R . .
C1 C -0.8499(2) -0.1807(2) -0.18185(5) 0.0105(3) Uani 1 1 d . . .
C13 C -0.6637(2) 0.0164(2) -0.11677(5) 0.0142(3) Uani 1 1 d . . .
H13A H -0.5787 0.0029 -0.0888 0.021 Uiso 1 1 calc R . .
H13B H -0.7865 0.0705 -0.1064 0.021 Uiso 1 1 calc R . .
H13C H -0.6035 0.0996 -0.1406 0.021 Uiso 1 1 calc R . .
C10 C -1.0402(2) -0.5781(2) -0.11278(5) 0.0144(3) Uani 1 1 d . . .
H10 H -1.0993 -0.6749 -0.1312 0.017 Uiso 1 1 calc R . .
C8 C -1.0268(2) -0.3903(2) -0.03737(5) 0.0195(3) Uani 1 1 d . . .
H8A H -0.9387 -0.4352 -0.0118 0.023 Uiso 1 1 calc R . .
H8B H -1.1397 -0.3329 -0.0214 0.023 Uiso 1 1 calc R . .
C11 C -0.8919(2) -0.4568(2) -0.13680(5) 0.0117(3) Uani 1 1 d . . .
H11 H -0.7988 -0.5395 -0.1543 0.014 Uiso 1 1 calc R . .
C9 C -1.0927(2) -0.5563(2) -0.06693(6) 0.0160(3) Uani 1 1 d . . .
C4 C -0.5111(2) -0.2441(2) -0.16482(5) 0.0127(3) Uani 1 1 d . . .
H4A H -0.5117 -0.3846 -0.1666 0.015 Uiso 1 1 calc R . .
C7 C -0.9243(2) -0.2399(2) -0.06734(5) 0.0143(3) Uani 1 1 d . . .
H7A H -0.8559 -0.1528 -0.0454 0.017 Uiso 1 1 calc R . .
H7B H -1.0210 -0.1662 -0.0855 0.017 Uiso 1 1 calc R . .
C3 C -0.5278(2) -0.1646(2) -0.21611(5) 0.0136(3) Uani 1 1 d . . .
H3A H -0.5124 -0.0262 -0.2166 0.016 Uiso 1 1 calc R . .
H3B H -0.4331 -0.2225 -0.2382 0.016 Uiso 1 1 calc R . .
C15 C -1.2195(2) -0.6960(2) -0.04139(6) 0.0215(3) Uani 1 1 d . . .
H15A H -1.2605 -0.7933 -0.0642 0.032 Uiso 1 1 calc R . .
H15B H -1.3327 -0.6312 -0.0285 0.032 Uiso 1 1 calc R . .
H15C H -1.1480 -0.7542 -0.0148 0.032 Uiso 1 1 calc R . .
C14 C -0.6227(2) -0.4323(2) -0.07547(5) 0.0169(3) Uani 1 1 d . . .
H14A H -0.5478 -0.3433 -0.0561 0.025 Uiso 1 1 calc R . .
H14B H -0.5377 -0.4960 -0.0985 0.025 Uiso 1 1 calc R . .
H14C H -0.6823 -0.5258 -0.0542 0.025 Uiso 1 1 calc R . .


_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 1.4485(17) . ?
O1 C11 1.4550(17) . ?
O3 H3 0.8400 . ?
O3 C4 1.4149(18) . ?
O2 H2 0.8400 . ?
O2 C2 1.4287(17) . ?
O4 H4 0.8400 . ?
O4 C12 1.4288(19) . ?
C6 C5 1.565(2) . ?
C6 C11 1.532(2) . ?
C6 C7 1.5388(19) . ?
C6 C14 1.533(2) . ?
C5 C1 1.5736(19) . ?
C5 C13 1.536(2) . ?
C5 C4 1.5562(19) . ?
C2 H2A 1.0000 . ?
C2 C1 1.5592(18) . ?
C2 C3 1.522(2) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C12 C1 1.5256(19) . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C10 H10 0.9500 . ?
C10 C11 1.500(2) . ?
C10 C9 1.330(2) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C8 C9 1.508(2) . ?
C8 C7 1.530(2) . ?
C11 H11 1.0000 . ?
C9 C15 1.505(2) . ?
C4 H4A 1.0000 . ?
C4 C3 1.5331(19) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 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 C11 107.69(10) . . ?
C4 O3 H3 109.5 . . ?
C2 O2 H2 109.5 . . ?
C12 O4 H4 109.5 . . ?
C11 C6 C5 101.50(11) . . ?
C11 C6 C7 107.42(12) . . ?
C11 C6 C14 111.55(12) . . ?
C7 C6 C5 112.51(12) . . ?
C14 C6 C5 113.51(12) . . ?
C14 C6 C7 109.95(11) . . ?
C6 C5 C1 103.36(11) . . ?
C13 C5 C6 113.40(12) . . ?
C13 C5 C1 115.14(12) . . ?
C13 C5 C4 108.88(12) . . ?
C4 C5 C6 112.76(12) . . ?
C4 C5 C1 102.83(11) . . ?
O2 C2 H2A 107.0 . . ?
O2 C2 C1 115.25(12) . . ?
O2 C2 C3 115.68(12) . . ?
C1 C2 H2A 107.0 . . ?
C3 C2 H2A 107.0 . . ?
C3 C2 C1 104.50(11) . . ?
O4 C12 H12A 109.7 . . ?
O4 C12 H12B 109.7 . . ?
O4 C12 C1 109.98(12) . . ?
H12A C12 H12B 108.2 . . ?
C1 C12 H12A 109.7 . . ?
C1 C12 H12B 109.7 . . ?
O1 C1 C5 106.94(11) . . ?
O1 C1 C2 110.85(11) . . ?
O1 C1 C12 103.75(11) . . ?
C2 C1 C5 105.64(11) . . ?
C12 C1 C5 117.85(11) . . ?
C12 C1 C2 111.72(12) . . ?
C5 C13 H13A 109.5 . . ?
C5 C13 H13B 109.5 . . ?
C5 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C11 C10 H10 118.5 . . ?
C9 C10 H10 118.5 . . ?
C9 C10 C11 123.04(14) . . ?
H8A C8 H8B 107.7 . . ?
C9 C8 H8A 108.9 . . ?
C9 C8 H8B 108.9 . . ?
C9 C8 C7 113.21(12) . . ?
C7 C8 H8A 108.9 . . ?
C7 C8 H8B 108.9 . . ?
O1 C11 C6 104.76(11) . . ?
O1 C11 C10 110.10(12) . . ?
O1 C11 H11 108.8 . . ?
C6 C11 H11 108.8 . . ?
C10 C11 C6 115.46(12) . . ?
C10 C11 H11 108.8 . . ?
C10 C9 C8 121.71(14) . . ?
C10 C9 C15 122.21(15) . . ?
C15 C9 C8 116.07(14) . . ?
O3 C4 C5 110.81(11) . . ?
O3 C4 H4A 108.8 . . ?
O3 C4 C3 115.53(12) . . ?
C5 C4 H4A 108.8 . . ?
C3 C4 C5 103.91(11) . . ?
C3 C4 H4A 108.8 . . ?
C6 C7 H7A 109.2 . . ?
C6 C7 H7B 109.2 . . ?
C8 C7 C6 112.13(13) . . ?
C8 C7 H7A 109.2 . . ?
C8 C7 H7B 109.2 . . ?
H7A C7 H7B 107.9 . . ?
C2 C3 C4 100.37(12) . . ?
C2 C3 H3A 111.7 . . ?
C2 C3 H3B 111.7 . . ?
C4 C3 H3A 111.7 . . ?
C4 C3 H3B 111.7 . . ?
H3A C3 H3B 109.5 . . ?
C9 C15 H15A 109.5 . . ?
C9 C15 H15B 109.5 . . ?
C9 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C6 C14 H14A 109.5 . . ?
C6 C14 H14B 109.5 . . ?
C6 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 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
O3 C4 C3 C2 -169.17(12) . . . . ?
O2 C2 C1 O1 94.36(14) . . . . ?
O2 C2 C1 C5 -150.15(11) . . . . ?
O2 C2 C1 C12 -20.82(17) . . . . ?
O2 C2 C3 C4 170.31(12) . . . . ?
O4 C12 C1 O1 -167.47(10) . . . . ?
O4 C12 C1 C5 74.60(15) . . . . ?
O4 C12 C1 C2 -48.00(15) . . . . ?
C6 C5 C1 O1 -6.40(14) . . . . ?
C6 C5 C1 C2 -124.54(12) . . . . ?
C6 C5 C1 C12 109.82(13) . . . . ?
C6 C5 C4 O3 -91.10(14) . . . . ?
C6 C5 C4 C3 144.21(12) . . . . ?
C5 C6 C11 O1 -39.41(13) . . . . ?
C5 C6 C11 C10 -160.68(12) . . . . ?
C5 C6 C7 C8 170.68(12) . . . . ?
C5 C4 C3 C2 -47.57(13) . . . . ?
C1 O1 C11 C6 37.10(13) . . . . ?
C1 O1 C11 C10 161.83(11) . . . . ?
C1 C5 C4 O3 158.26(11) . . . . ?
C1 C5 C4 C3 33.57(14) . . . . ?
C1 C2 C3 C4 42.49(13) . . . . ?
C13 C5 C1 O1 -130.62(12) . . . . ?
C13 C5 C1 C2 111.24(13) . . . . ?
C13 C5 C1 C12 -14.40(18) . . . . ?
C13 C5 C4 O3 35.69(15) . . . . ?
C13 C5 C4 C3 -89.00(13) . . . . ?
C11 O1 C1 C5 -18.65(13) . . . . ?
C11 O1 C1 C2 96.03(13) . . . . ?
C11 O1 C1 C12 -143.91(11) . . . . ?
C11 C6 C5 C1 27.14(13) . . . . ?
C11 C6 C5 C13 152.48(11) . . . . ?
C11 C6 C5 C4 -83.18(14) . . . . ?
C11 C6 C7 C8 59.81(15) . . . . ?
C11 C10 C9 C8 8.6(2) . . . . ?
C11 C10 C9 C15 -170.88(14) . . . . ?
C9 C10 C11 O1 -108.75(16) . . . . ?
C9 C10 C11 C6 9.6(2) . . . . ?
C9 C8 C7 C6 -44.26(17) . . . . ?
C4 C5 C1 O1 111.11(12) . . . . ?
C4 C5 C1 C2 -7.02(14) . . . . ?
C4 C5 C1 C12 -132.66(13) . . . . ?
C7 C6 C5 C1 -87.39(14) . . . . ?
C7 C6 C5 C13 37.96(16) . . . . ?
C7 C6 C5 C4 162.30(12) . . . . ?
C7 C6 C11 O1 78.84(14) . . . . ?
C7 C6 C11 C10 -42.43(16) . . . . ?
C7 C8 C9 C10 9.1(2) . . . . ?
C7 C8 C9 C15 -171.34(13) . . . . ?
C3 C2 C1 O1 -137.55(12) . . . . ?
C3 C2 C1 C5 -22.06(14) . . . . ?
C3 C2 C1 C12 107.27(13) . . . . ?
C14 C6 C5 C1 146.96(12) . . . . ?
C14 C6 C5 C13 -87.70(15) . . . . ?
C14 C6 C5 C4 36.64(17) . . . . ?
C14 C6 C11 O1 -160.61(11) . . . . ?
C14 C6 C11 C10 78.12(15) . . . . ?
C14 C6 C7 C8 -61.75(16) . . . . ?

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_exp_1133
_database_code_depnum_ccdc_archive 'CCDC 1516459'
_audit_update_record             
;
2016-11-11 deposited with the CCDC.
2017-01-09 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C29 H38.50 O11.25'
_chemical_formula_weight         567.10

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'

_symmetry_cell_setting           ?
_symmetry_space_group_name_H-M   p212121

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'

_cell_length_a                   10.4204(3)
_cell_length_b                   13.0839(3)
_cell_length_c                   20.0354(7)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     2731.60(14)
_cell_formula_units_Z            4
_cell_measurement_temperature    103(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.60
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.379
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1210
_exptl_absorpt_coefficient_mu    0.886
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  0.6184
_exptl_absorpt_correction_T_max  0.8427
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      103(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            9712
_diffrn_reflns_av_R_equivalents  0.0176
_diffrn_reflns_av_sigmaI/netI    0.0275
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         4.04
_diffrn_reflns_theta_max         71.76
_reflns_number_total             5222
_reflns_number_gt                5042
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0551P)²+0.6857P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.03(13)
_refine_ls_number_reflns         5222
_refine_ls_number_parameters     386
_refine_ls_number_restraints     6
_refine_ls_R_factor_all          0.0367
_refine_ls_R_factor_gt           0.0351
_refine_ls_wR_factor_ref         0.0925
_refine_ls_wR_factor_gt          0.0909
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_restrained_S_all      1.031
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O9 O 0.50997(12) 0.91594(9) 0.06908(6) 0.0204(3) Uani 1 1 d . . .
O4 O 0.92907(13) 1.34392(9) 0.15037(6) 0.0213(3) Uani 1 1 d . . .
O6 O 0.60005(13) 1.50166(9) 0.24958(6) 0.0219(3) Uani 1 1 d . . .
O5 O 0.82557(12) 0.99011(9) -0.05530(6) 0.0200(3) Uani 1 1 d . . .
C15 C 0.54645(18) 1.26675(13) 0.14482(8) 0.0193(4) Uani 1 1 d . . .
H15A H 0.4526 1.2740 0.1386 0.023 Uiso 1 1 calc R . .
H15B H 0.5898 1.3002 0.1066 0.023 Uiso 1 1 calc R . .
O3 O 0.85007(13) 1.24432(10) 0.06795(6) 0.0247(3) Uani 1 1 d . . .
O10 O 0.89142(13) 1.37773(10) 0.31195(7) 0.0242(3) Uani 1 1 d . . .
O8 O 0.71103(13) 0.80308(10) -0.01240(7) 0.0227(3) Uani 1 1 d . . .
H8 H 0.6348 0.7832 -0.0082 0.034 Uiso 1 1 calc R . .
C25 C 0.91782(17) 1.01117(12) 0.05730(8) 0.0176(3) Uani 1 1 d . . .
H25A H 0.9584 0.9703 0.0931 0.021 Uiso 1 1 calc R . .
H25B H 0.8512 1.0550 0.0778 0.021 Uiso 1 1 calc R . .
C8 C 0.54231(18) 1.43240(12) 0.20183(8) 0.0187(4) Uani 1 1 d . . .
H8A H 0.5655 1.4558 0.1559 0.022 Uiso 1 1 calc R . .
C11 C 0.76681(17) 1.38716(13) 0.28132(9) 0.0197(4) Uani 1 1 d . . .
O7 O 0.98898(13) 0.79892(10) 0.03295(6) 0.0234(3) Uani 1 1 d . . .
O1 O 0.41333(13) 1.11831(10) 0.07941(7) 0.0287(3) Uani 1 1 d . . .
C3 C 0.58694(17) 1.31927(12) 0.21012(8) 0.0163(3) Uani 1 1 d . . .
O2 O 0.58019(12) 1.15895(9) 0.14638(6) 0.0180(3) Uani 1 1 d . . .
C2 C 0.73726(18) 1.31777(13) 0.22159(8) 0.0175(3) Uani 1 1 d . . .
C16 C 0.51130(17) 1.09698(13) 0.10742(9) 0.0184(3) Uani 1 1 d . . .
C17 C 0.57931(17) 0.99573(13) 0.10233(8) 0.0173(3) Uani 1 1 d . . .
H17 H 0.6324 0.9749 0.1416 0.021 Uiso 1 1 calc R . .
C12 C 0.77692(19) 1.35990(15) 0.35133(9) 0.0243(4) Uani 1 1 d . . .
H12A H 0.7528 1.4121 0.3848 0.029 Uiso 1 1 calc R . .
H12B H 0.7569 1.2886 0.3641 0.029 Uiso 1 1 calc R . .
C13 C 0.79496(18) 1.21112(13) 0.23144(9) 0.0195(3) Uani 1 1 d . . .
H13A H 0.8853 1.2175 0.2443 0.029 Uiso 1 1 calc R . .
H13B H 0.7886 1.1725 0.1897 0.029 Uiso 1 1 calc R . .
H13C H 0.7478 1.1752 0.2667 0.029 Uiso 1 1 calc R . .
C21 C 0.85539(17) 0.93937(13) 0.00598(8) 0.0166(3) Uani 1 1 d . . .
C1 C 0.80077(18) 1.38145(13) 0.16360(9) 0.0193(4) Uani 1 1 d . . .
H1 H 0.7470 1.3779 0.1223 0.023 Uiso 1 1 calc R . .
C19 C 0.59941(18) 1.01487(14) -0.02822(9) 0.0224(4) Uani 1 1 d . . .
H19A H 0.5330 1.0680 -0.0216 0.027 Uiso 1 1 calc R . .
H19B H 0.5692 0.9672 -0.0632 0.027 Uiso 1 1 calc R . .
C10 C 0.8095(2) 1.49240(13) 0.18910(9) 0.0237(4) Uani 1 1 d . . .
H10A H 0.9001 1.5128 0.1957 0.028 Uiso 1 1 calc R . .
H10B H 0.7691 1.5401 0.1570 0.028 Uiso 1 1 calc R . .
C26 C 1.02005(18) 1.07885(14) 0.02334(9) 0.0218(4) Uani 1 1 d . . .
H26A H 1.0772 1.0352 -0.0039 0.026 Uiso 1 1 calc R . .
H26B H 0.9769 1.1277 -0.0070 0.026 Uiso 1 1 calc R . .
C4 C 0.51493(17) 1.27163(13) 0.26955(8) 0.0176(3) Uani 1 1 d . . .
H4A H 0.5412 1.1993 0.2742 0.021 Uiso 1 1 calc R . .
H4B H 0.5400 1.3078 0.3109 0.021 Uiso 1 1 calc R . .
C9 C 0.73688(18) 1.49259(13) 0.25565(9) 0.0207(4) Uani 1 1 d . . .
H9 H 0.7718 1.5461 0.2863 0.025 Uiso 1 1 calc R . .
C29 C 0.93729(18) 1.26828(13) 0.10444(9) 0.0203(4) Uani 1 1 d . . .
C14 C 0.1825(2) 1.40325(16) 0.25172(10) 0.0288(4) Uani 1 1 d . . .
H14A H 0.1669 1.4090 0.2998 0.043 Uiso 1 1 calc R . .
H14B H 0.1298 1.3480 0.2333 0.043 Uiso 1 1 calc R . .
H14C H 0.1599 1.4678 0.2299 0.043 Uiso 1 1 calc R . .
C22 C 0.73497(17) 0.88446(13) 0.03314(8) 0.0172(3) Uani 1 1 d . . .
H22 H 0.7528 0.8563 0.0786 0.021 Uiso 1 1 calc R . .
C28 C 1.06514(18) 1.21992(14) 0.10748(10) 0.0239(4) Uani 1 1 d . . .
H28 H 1.1274 1.2498 0.1361 0.029 Uiso 1 1 calc R . .
O11 O 0.7825(2) 1.58832(16) 0.02531(10) 0.0550(5) Uani 1 1 d D . .
C24 C 0.9946(2) 0.84310(14) -0.08228(9) 0.0231(4) Uani 1 1 d . . .
H24A H 1.0495 0.9010 -0.0944 0.035 Uiso 1 1 calc R . .
H24B H 0.9193 0.8417 -0.1116 0.035 Uiso 1 1 calc R . .
H24C H 1.0428 0.7793 -0.0873 0.035 Uiso 1 1 calc R . .
C7 C 0.40050(19) 1.44710(13) 0.21141(9) 0.0207(4) Uani 1 1 d . . .
H7 H 0.3642 1.5094 0.1959 0.025 Uiso 1 1 calc R . .
C6 C 0.32192(18) 1.38022(14) 0.23969(9) 0.0216(4) Uani 1 1 d . . .
C27 C 1.09943(18) 1.13737(14) 0.07287(10) 0.0245(4) Uani 1 1 d . . .
H27 H 1.1839 1.1126 0.0804 0.029 Uiso 1 1 calc R . .
C20 C 0.72558(19) 1.06430(14) -0.04954(9) 0.0224(4) Uani 1 1 d . . .
H20A H 0.7136 1.0989 -0.0930 0.027 Uiso 1 1 calc R . .
H20B H 0.7506 1.1166 -0.0163 0.027 Uiso 1 1 calc R . .
C5 C 0.36925(18) 1.27673(14) 0.26183(9) 0.0214(4) Uani 1 1 d . . .
H5A H 0.3418 1.2249 0.2288 0.026 Uiso 1 1 calc R . .
H5B H 0.3288 1.2594 0.3051 0.026 Uiso 1 1 calc R . .
C18 C 0.62187(17) 0.95770(13) 0.03612(8) 0.0174(3) Uani 1 1 d . . .
C23 C 0.95192(17) 0.85426(13) -0.01160(8) 0.0179(3) Uani 1 1 d . . .
O12 O 0.9181(8) 0.7036(6) 0.1588(3) 0.0486(19) Uani 0.25 1 d PD . .
H11A H 0.769(3) 1.6515(7) 0.0181(16) 0.073 Uiso 1 1 d D . .
H11B H 0.839(2) 1.567(2) -0.0017(13) 0.073 Uiso 1 1 d D . .
H12C H 0.930(11) 0.764(4) 0.145(7) 0.073 Uiso 0.25 1 d PD . .
H12D H 0.988(6) 0.670(8) 0.155(8) 0.073 Uiso 0.25 1 d PD . .


_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
O9 C17 1.434(2) . ?
O9 C18 1.447(2) . ?
O4 C29 1.354(2) . ?
O4 C1 1.449(2) . ?
O6 C9 1.436(2) . ?
O6 C8 1.449(2) . ?
O5 C20 1.429(2) . ?
O5 C21 1.4299(19) . ?
C15 O2 1.4540(19) . ?
C15 C3 1.537(2) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
O3 C29 1.208(2) . ?
O10 C11 1.442(2) . ?
O10 C12 1.449(2) . ?
O8 C22 1.424(2) . ?
O8 H8 0.8400 . ?
C25 C21 1.537(2) . ?
C25 C26 1.543(2) . ?
C25 H25A 0.9900 . ?
C25 H25B 0.9900 . ?
C8 C7 1.503(3) . ?
C8 C3 1.560(2) . ?
C8 H8A 1.0000 . ?
C11 C12 1.451(2) . ?
C11 C9 1.505(2) . ?
C11 C2 1.533(2) . ?
O7 C23 1.212(2) . ?
O1 C16 1.198(2) . ?
C3 C4 1.539(2) . ?
C3 C2 1.583(3) . ?
O2 C16 1.335(2) . ?
C2 C13 1.532(2) . ?
C2 C1 1.576(2) . ?
C16 C17 1.506(2) . ?
C17 C18 1.485(2) . ?
C17 H17 1.0000 . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C21 C23 1.541(2) . ?
C21 C22 1.545(2) . ?
C1 C10 1.542(2) . ?
C1 H1 1.0000 . ?
C19 C18 1.509(2) . ?
C19 C20 1.526(3) . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
C10 C9 1.533(3) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C26 C27 1.502(3) . ?
C26 H26A 0.9900 . ?
C26 H26B 0.9900 . ?
C4 C5 1.527(3) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C9 H9 1.0000 . ?
C29 C28 1.476(3) . ?
C14 C6 1.503(3) . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C22 C18 1.520(2) . ?
C22 H22 1.0000 . ?
C28 C27 1.332(3) . ?
C28 H28 0.9500 . ?
O11 H11A 0.8502(10) . ?
O11 H11B 0.8502(10) . ?
C24 C23 1.491(2) . ?
C24 H24A 0.9800 . ?
C24 H24B 0.9800 . ?
C24 H24C 0.9800 . ?
C7 C6 1.326(3) . ?
C7 H7 0.9500 . ?
C6 C5 1.508(3) . ?
C27 H27 0.9500 . ?
C20 H20A 0.9900 . ?
C20 H20B 0.9900 . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
O12 H12C 0.850(10) . ?
O12 H12D 0.851(10) . ?

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
C17 O9 C18 62.04(10) . . ?
C29 O4 C1 115.50(14) . . ?
C9 O6 C8 114.62(13) . . ?
C20 O5 C21 113.86(13) . . ?
O2 C15 C3 110.43(13) . . ?
O2 C15 H15A 109.6 . . ?
C3 C15 H15A 109.6 . . ?
O2 C15 H15B 109.6 . . ?
C3 C15 H15B 109.6 . . ?
H15A C15 H15B 108.1 . . ?
C11 O10 C12 60.26(11) . . ?
C22 O8 H8 109.5 . . ?
C21 C25 C26 110.35(14) . . ?
C21 C25 H25A 109.6 . . ?
C26 C25 H25A 109.6 . . ?
C21 C25 H25B 109.6 . . ?
C26 C25 H25B 109.6 . . ?
H25A C25 H25B 108.1 . . ?
O6 C8 C7 104.13(14) . . ?
O6 C8 C3 113.54(14) . . ?
C7 C8 C3 113.64(15) . . ?
O6 C8 H8A 108.4 . . ?
C7 C8 H8A 108.4 . . ?
C3 C8 H8A 108.4 . . ?
O10 C11 C12 60.13(12) . . ?
O10 C11 C9 114.24(14) . . ?
C12 C11 C9 124.79(16) . . ?
O10 C11 C2 117.55(14) . . ?
C12 C11 C2 128.57(16) . . ?
C9 C11 C2 103.56(14) . . ?
C15 C3 C4 110.10(14) . . ?
C15 C3 C8 104.57(13) . . ?
C4 C3 C8 108.73(13) . . ?
C15 C3 C2 112.93(14) . . ?
C4 C3 C2 111.41(13) . . ?
C8 C3 C2 108.79(14) . . ?
C16 O2 C15 116.53(14) . . ?
C13 C2 C11 111.09(14) . . ?
C13 C2 C1 114.32(15) . . ?
C11 C2 C1 100.26(13) . . ?
C13 C2 C3 114.72(14) . . ?
C11 C2 C3 107.73(14) . . ?
C1 C2 C3 107.58(13) . . ?
O1 C16 O2 126.21(16) . . ?
O1 C16 C17 125.04(16) . . ?
O2 C16 C17 108.72(14) . . ?
O9 C17 C18 59.42(10) . . ?
O9 C17 C16 115.78(14) . . ?
C18 C17 C16 119.73(15) . . ?
O9 C17 H17 116.5 . . ?
C18 C17 H17 116.5 . . ?
C16 C17 H17 116.5 . . ?
O10 C12 C11 59.60(11) . . ?
O10 C12 H12A 117.8 . . ?
C11 C12 H12A 117.8 . . ?
O10 C12 H12B 117.8 . . ?
C11 C12 H12B 117.8 . . ?
H12A C12 H12B 114.9 . . ?
C2 C13 H13A 109.5 . . ?
C2 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C2 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
O5 C21 C25 112.50(13) . . ?
O5 C21 C23 106.32(13) . . ?
C25 C21 C23 108.55(14) . . ?
O5 C21 C22 109.99(14) . . ?
C25 C21 C22 113.10(13) . . ?
C23 C21 C22 105.94(13) . . ?
O4 C1 C10 109.00(15) . . ?
O4 C1 C2 110.08(14) . . ?
C10 C1 C2 106.16(13) . . ?
O4 C1 H1 110.5 . . ?
C10 C1 H1 110.5 . . ?
C2 C1 H1 110.5 . . ?
C18 C19 C20 108.40(15) . . ?
C18 C19 H19A 110.0 . . ?
C20 C19 H19A 110.0 . . ?
C18 C19 H19B 110.0 . . ?
C20 C19 H19B 110.0 . . ?
H19A C19 H19B 108.4 . . ?
C9 C10 C1 105.12(14) . . ?
C9 C10 H10A 110.7 . . ?
C1 C10 H10A 110.7 . . ?
C9 C10 H10B 110.7 . . ?
C1 C10 H10B 110.7 . . ?
H10A C10 H10B 108.8 . . ?
C27 C26 C25 112.41(15) . . ?
C27 C26 H26A 109.1 . . ?
C25 C26 H26A 109.1 . . ?
C27 C26 H26B 109.1 . . ?
C25 C26 H26B 109.1 . . ?
H26A C26 H26B 107.9 . . ?
C5 C4 C3 112.86(14) . . ?
C5 C4 H4A 109.0 . . ?
C3 C4 H4A 109.0 . . ?
C5 C4 H4B 109.0 . . ?
C3 C4 H4B 109.0 . . ?
H4A C4 H4B 107.8 . . ?
O6 C9 C11 108.09(14) . . ?
O6 C9 C10 114.61(15) . . ?
C11 C9 C10 101.16(14) . . ?
O6 C9 H9 110.9 . . ?
C11 C9 H9 110.9 . . ?
C10 C9 H9 110.9 . . ?
O3 C29 O4 123.60(17) . . ?
O3 C29 C28 126.36(17) . . ?
O4 C29 C28 110.02(16) . . ?
C6 C14 H14A 109.5 . . ?
C6 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C6 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
O8 C22 C18 111.14(14) . . ?
O8 C22 C21 105.33(13) . . ?
C18 C22 C21 110.51(14) . . ?
O8 C22 H22 109.9 . . ?
C18 C22 H22 109.9 . . ?
C21 C22 H22 109.9 . . ?
C27 C28 C29 124.62(18) . . ?
C27 C28 H28 117.7 . . ?
C29 C28 H28 117.7 . . ?
H11A O11 H11B 109.3(3) . . ?
C23 C24 H24A 109.5 . . ?
C23 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
C23 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
C6 C7 C8 125.28(16) . . ?
C6 C7 H7 117.4 . . ?
C8 C7 H7 117.4 . . ?
C7 C6 C14 122.22(18) . . ?
C7 C6 C5 121.10(17) . . ?
C14 C6 C5 116.68(17) . . ?
C28 C27 C26 127.55(18) . . ?
C28 C27 H27 116.2 . . ?
C26 C27 H27 116.2 . . ?
O5 C20 C19 111.28(14) . . ?
O5 C20 H20A 109.4 . . ?
C19 C20 H20A 109.4 . . ?
O5 C20 H20B 109.4 . . ?
C19 C20 H20B 109.4 . . ?
H20A C20 H20B 108.0 . . ?
C6 C5 C4 113.21(15) . . ?
C6 C5 H5A 108.9 . . ?
C4 C5 H5A 108.9 . . ?
C6 C5 H5B 108.9 . . ?
C4 C5 H5B 108.9 . . ?
H5A C5 H5B 107.7 . . ?
O9 C18 C17 58.54(10) . . ?
O9 C18 C19 116.88(14) . . ?
C17 C18 C19 123.43(15) . . ?
O9 C18 C22 113.86(14) . . ?
C17 C18 C22 118.55(14) . . ?
C19 C18 C22 113.53(14) . . ?
O7 C23 C24 123.07(16) . . ?
O7 C23 C21 118.11(15) . . ?
C24 C23 C21 118.82(15) . . ?
H12C O12 H12D 109(3) . . ?

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
C9 O6 C8 C7 172.83(14) . . . . ?
C9 O6 C8 C3 48.73(19) . . . . ?
C12 O10 C11 C9 117.58(17) . . . . ?
C12 O10 C11 C2 -120.75(18) . . . . ?
O2 C15 C3 C4 -62.12(18) . . . . ?
O2 C15 C3 C8 -178.77(14) . . . . ?
O2 C15 C3 C2 63.11(18) . . . . ?
O6 C8 C3 C15 -164.60(14) . . . . ?
C7 C8 C3 C15 76.63(18) . . . . ?
O6 C8 C3 C4 77.81(18) . . . . ?
C7 C8 C3 C4 -40.96(19) . . . . ?
O6 C8 C3 C2 -43.69(19) . . . . ?
C7 C8 C3 C2 -162.46(14) . . . . ?
C3 C15 O2 C16 155.19(15) . . . . ?
O10 C11 C2 C13 37.9(2) . . . . ?
C12 C11 C2 C13 -34.5(3) . . . . ?
C9 C11 C2 C13 164.93(15) . . . . ?
O10 C11 C2 C1 -83.32(17) . . . . ?
C12 C11 C2 C1 -155.72(18) . . . . ?
C9 C11 C2 C1 43.71(17) . . . . ?
O10 C11 C2 C3 164.34(14) . . . . ?
C12 C11 C2 C3 91.9(2) . . . . ?
C9 C11 C2 C3 -68.63(17) . . . . ?
C15 C3 C2 C13 -65.07(18) . . . . ?
C4 C3 C2 C13 59.45(18) . . . . ?
C8 C3 C2 C13 179.31(13) . . . . ?
C15 C3 C2 C11 170.66(13) . . . . ?
C4 C3 C2 C11 -64.82(17) . . . . ?
C8 C3 C2 C11 55.03(17) . . . . ?
C15 C3 C2 C1 63.36(17) . . . . ?
C4 C3 C2 C1 -172.13(12) . . . . ?
C8 C3 C2 C1 -52.27(17) . . . . ?
C15 O2 C16 O1 -12.1(3) . . . . ?
C15 O2 C16 C17 166.06(14) . . . . ?
C18 O9 C17 C16 110.75(16) . . . . ?
O1 C16 C17 O9 -9.4(3) . . . . ?
O2 C16 C17 O9 172.41(13) . . . . ?
O1 C16 C17 C18 58.6(2) . . . . ?
O2 C16 C17 C18 -119.60(17) . . . . ?
C9 C11 C12 O10 -100.23(19) . . . . ?
C2 C11 C12 O10 103.0(2) . . . . ?
C20 O5 C21 C25 -68.08(19) . . . . ?
C20 O5 C21 C23 173.23(14) . . . . ?
C20 O5 C21 C22 58.96(18) . . . . ?
C26 C25 C21 O5 -43.53(19) . . . . ?
C26 C25 C21 C23 73.85(17) . . . . ?
C26 C25 C21 C22 -168.89(14) . . . . ?
C29 O4 C1 C10 -154.39(14) . . . . ?
C29 O4 C1 C2 89.56(17) . . . . ?
C13 C2 C1 O4 -22.86(19) . . . . ?
C11 C2 C1 O4 96.03(15) . . . . ?
C3 C2 C1 O4 -151.51(13) . . . . ?
C13 C2 C1 C10 -140.69(16) . . . . ?
C11 C2 C1 C10 -21.80(17) . . . . ?
C3 C2 C1 C10 90.66(16) . . . . ?
O4 C1 C10 C9 -125.50(16) . . . . ?
C2 C1 C10 C9 -6.96(19) . . . . ?
C21 C25 C26 C27 -170.20(15) . . . . ?
C15 C3 C4 C5 -56.86(18) . . . . ?
C8 C3 C4 C5 57.16(18) . . . . ?
C2 C3 C4 C5 177.05(14) . . . . ?
C8 O6 C9 C11 -63.09(18) . . . . ?
C8 O6 C9 C10 48.84(19) . . . . ?
O10 C11 C9 O6 -159.17(13) . . . . ?
C12 C11 C9 O6 -89.8(2) . . . . ?
C2 C11 C9 O6 71.75(17) . . . . ?
O10 C11 C9 C10 80.11(17) . . . . ?
C12 C11 C9 C10 149.49(18) . . . . ?
C2 C11 C9 C10 -48.97(17) . . . . ?
C1 C10 C9 O6 -82.33(18) . . . . ?
C1 C10 C9 C11 33.68(18) . . . . ?
C1 O4 C29 O3 12.5(2) . . . . ?
C1 O4 C29 C28 -166.11(14) . . . . ?
O5 C21 C22 O8 68.56(16) . . . . ?
C25 C21 C22 O8 -164.74(13) . . . . ?
C23 C21 C22 O8 -45.95(17) . . . . ?
O5 C21 C22 C18 -51.56(17) . . . . ?
C25 C21 C22 C18 75.15(18) . . . . ?
C23 C21 C22 C18 -166.07(13) . . . . ?
O3 C29 C28 C27 -4.8(3) . . . . ?
O4 C29 C28 C27 173.77(18) . . . . ?
O6 C8 C7 C6 -108.12(18) . . . . ?
C3 C8 C7 C6 15.9(2) . . . . ?
C8 C7 C6 C14 175.77(16) . . . . ?
C8 C7 C6 C5 -3.9(3) . . . . ?
C29 C28 C27 C26 1.9(3) . . . . ?
C25 C26 C27 C28 -75.6(3) . . . . ?
C21 O5 C20 C19 -62.26(19) . . . . ?
C18 C19 C20 O5 55.92(19) . . . . ?
C7 C6 C5 C4 18.7(2) . . . . ?
C14 C6 C5 C4 -160.93(15) . . . . ?
C3 C4 C5 C6 -46.3(2) . . . . ?
C17 O9 C18 C19 -114.46(17) . . . . ?
C17 O9 C18 C22 110.00(16) . . . . ?
C16 C17 C18 O9 -104.14(17) . . . . ?
O9 C17 C18 C19 103.37(18) . . . . ?
C16 C17 C18 C19 -0.8(3) . . . . ?
O9 C17 C18 C22 -101.95(16) . . . . ?
C16 C17 C18 C22 153.91(16) . . . . ?
C20 C19 C18 O9 172.50(14) . . . . ?
C20 C19 C18 C17 104.00(19) . . . . ?
C20 C19 C18 C22 -51.82(19) . . . . ?
O8 C22 C18 O9 71.05(18) . . . . ?
C21 C22 C18 O9 -172.39(13) . . . . ?
O8 C22 C18 C17 136.91(15) . . . . ?
C21 C22 C18 C17 -106.53(17) . . . . ?
O8 C22 C18 C19 -66.00(19) . . . . ?
C21 C22 C18 C19 50.57(19) . . . . ?
O5 C21 C23 O7 -178.28(15) . . . . ?
C25 C21 C23 O7 60.5(2) . . . . ?
C22 C21 C23 O7 -61.27(19) . . . . ?
O5 C21 C23 C24 1.2(2) . . . . ?
C25 C21 C23 C24 -120.02(17) . . . . ?
C22 C21 C23 C24 118.23(17) . . . . ?

_diffrn_measured_fraction_theta_max 0.988
_diffrn_reflns_theta_full        71.76
_diffrn_measured_fraction_theta_full 0.988
_refine_diff_density_max         0.279
_refine_diff_density_min         -0.311
_refine_diff_density_rms         0.043
_exptl_crystal_recrystallization_method 'Vapour deposition'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_exp_1485
_database_code_depnum_ccdc_archive 'CCDC 1516457'
_audit_update_record             
;
2016-11-11 deposited with the CCDC.
2017-01-09 downloaded from the CCDC.
;
_audit_creation_date             2016-11-11
_audit_creation_method           
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_chemical_formula_moiety         'C15 H22 O4'
_chemical_formula_sum            'C15 H22 O4'
_chemical_formula_weight         266.34
_chemical_absolute_configuration unk
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
_atom_type_scat_dispersion_source
H 0.00000 0.00000 0.49300 0.32291 0.14019 0.04081 10.51090 26.12570 3.14236
57.79970 0.0030380000826
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
C 0.01920 0.00962 2.31000 1.02000 1.58860 0.86500 20.84390 10.20750 0.56870
51.65120 0.215599998832
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
O 0.05239 0.03377 3.04850 2.28680 1.54630 0.86700 13.27710 5.70110 0.32390
32.90890 0.250800013542
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'

_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_id
_space_group_symop_operation_xyz
1 x,y,z
2 x+1/2,-y+1/2,-z
3 -x,y+1/2,-z+1/2
4 -x+1/2,-y,z+1/2

_symmetry_Int_Tables_number      19
_cell_length_a                   6.4486(3)
_cell_length_b                   11.3707(10)
_cell_length_c                   17.7648(15)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1302.61(17)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2202
_cell_measurement_temperature    98.8
_cell_measurement_theta_max      71.5643
_cell_measurement_theta_min      3.8803
_exptl_absorpt_coefficient_mu    0.792
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.92921
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_density_diffrn    1.3580
_exptl_crystal_F_000             577.9299
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.08
_diffrn_reflns_av_R_equivalents  0.0191
_diffrn_reflns_av_unetI/netI     0.0324
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            4098
_diffrn_reflns_theta_full        71.8036
_diffrn_reflns_theta_max         71.80
_diffrn_reflns_theta_min         4.62
_diffrn_ambient_temperature      98.8
_diffrn_detector_area_resol_mean 16.0971
_diffrn_measured_fraction_theta_full 0.9819
_diffrn_measured_fraction_theta_max 0.9819
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -27.00   -1.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -        0.0000  128.0000  -28.0000 26

#__ type_ start__ end____ width___ exp.time_
  2 omega    2.00   28.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -        0.0000   52.0000   94.0000 26

#__ type_ start__ end____ width___ exp.time_
  3 omega  -60.00   26.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -42.5000   77.0000  -90.0000 86

#__ type_ start__ end____ width___ exp.time_
  4 omega  -20.00   18.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -42.5000   37.0000    0.0000 38

#__ type_ start__ end____ width___ exp.time_
  5 omega -112.00  -32.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -42.5000  -52.0000   85.0000 80

#__ type_ start__ end____ width___ exp.time_
  6 omega  -45.00   19.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -42.5000   37.0000 -150.0000 64

#__ type_ start__ end____ width___ exp.time_
  7 omega   56.00   98.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -45.0000   90.0000 42

#__ type_ start__ end____ width___ exp.time_
  8 omega   91.00  178.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   45.0000   30.0000 87

#__ type_ start__ end____ width___ exp.time_
  9 omega   59.00  164.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   15.0000 -180.0000 105

#__ type_ start__ end____ width___ exp.time_
 10 omega   47.00   85.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -45.0000 -150.0000 38

#__ type_ start__ end____ width___ exp.time_
 11 omega   41.00   89.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -45.0000  150.0000 48

#__ type_ start__ end____ width___ exp.time_
 12 omega  112.00  177.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  111.0000  120.0000 65

#__ type_ start__ end____ width___ exp.time_
 13 omega   50.00   82.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -45.0000   60.0000 32
;
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.1414924000
_diffrn_orient_matrix_UB_12      0.0929040000
_diffrn_orient_matrix_UB_13      0.0364829000
_diffrn_orient_matrix_UB_21      0.0557342000
_diffrn_orient_matrix_UB_22      -0.0478711000
_diffrn_orient_matrix_UB_23      0.0784247000
_diffrn_orient_matrix_UB_31      0.1845060000
_diffrn_orient_matrix_UB_32      0.0859673000
_diffrn_orient_matrix_UB_33      0.0042630000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Enhance (Cu) X-ray Source'
_reflns_Friedel_coverage         0.970
_reflns_limit_h_max              7
_reflns_limit_h_min              -7
_reflns_limit_k_max              13
_reflns_limit_k_min              -13
_reflns_limit_l_max              21
_reflns_limit_l_min              -21
_reflns_number_gt                2391
_reflns_number_total             2490
_reflns_odcompleteness_completeness 99.93
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_threshold_expression     I>=2u(I)
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine (Bourhis et al., 2015)'
_computing_structure_solution    'XS (Sheldrick, 2008)'
_refine_diff_density_max         0.3969
_refine_diff_density_min         -0.2546
_refine_diff_density_rms         0.0536
_refine_ls_abs_structure_details 
'Flack, H. D. (1983). Acta Cryst. A39, 876-881.'
_refine_ls_abs_structure_Flack   0.2(2)
_refine_ls_d_res_high            0.8115
_refine_ls_d_res_low             9.5769
_refine_ls_goodness_of_fit_ref   1.0502
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    34
_refine_ls_number_parameters     176
_refine_ls_number_reflns         2490
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0419
_refine_ls_R_factor_gt           0.0404
_refine_ls_restrained_S_all      1.0502
_refine_ls_shift/su_max          0.0002
_refine_ls_shift/su_mean         0.0001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0682P)²+0.2180P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1036
_refine_ls_wR_factor_ref         0.1049
_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:
 C11(H11), C9(H9)
2.b Secondary CH2 refined with riding coordinates:
 C3(H3a,H3b), C5(H5a,H5b), C15(H15a,H15b), C10(H10a,H10b)
2.c Aromatic/amide H refined with riding coordinates:
 C1(H1)
2.d Idealised Me refined as rotating group:
 C14(H14a,H14b,H14c), C13(H13a,H13b,H13c), C12(H12a,H12b,H12c)
2.e Idealised tetrahedral OH refined as rotating group:
 O3(H3), O4(H4)
;
_atom_sites_solution_primary     direct
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_refinement_flags_posn
O1 O -0.09697(19) -0.09806(11) -0.27465(6) 0.0149(3) Uani 1.000000 .
O3 O 0.3854(2) -0.22253(12) -0.44222(7) 0.0212(3) Uani 1.000000 .
H3 H 0.2979(17) -0.1815(19) -0.4630(6) 0.0317(4) Uiso 1.000000 GR
O2 O -0.09382(19) -0.29438(11) -0.26409(7) 0.0166(3) Uani 1.000000 .
C1 C -0.1056(3) -0.18360(15) -0.14942(10) 0.0164(3) Uani 1.000000 .
H1 H -0.2394(3) -0.21072(15) -0.14041(10) 0.0197(4) Uiso 1.000000 R
C0aa C -0.0217(3) -0.19070(16) -0.22713(10) 0.0143(3) Uani 1.000000 .
C2 C 0.0023(3) -0.14025(15) -0.09247(10) 0.0174(4) Uani 1.000000 .
C3 C 0.2205(3) -0.09467(17) -0.10202(10) 0.0190(4) Uani 1.000000 .
H3a H 0.2334(3) -0.02058(17) -0.07536(10) 0.0228(4) Uiso 1.000000 R
H3b H 0.3162(3) -0.14997(17) -0.07914(10) 0.0228(4) Uiso 1.000000 R
O4 O 0.0377(2) -0.09920(12) -0.47587(7) 0.0213(3) Uani 1.000000 .
H4 H -0.027(2) -0.1525(16) -0.4960(8) 0.0319(5) Uiso 1.000000 GR
C5 C 0.2830(3) -0.07595(15) -0.18446(10) 0.0158(4) Uani 1.000000 .
H5a H 0.2192(3) -0.00433(15) -0.20300(10) 0.0190(4) Uiso 1.000000 R
H5b H 0.4322(3) -0.06640(15) -0.18752(10) 0.0190(4) Uiso 1.000000 R
C6 C 0.2163(3) -0.18025(14) -0.23479(9) 0.0134(3) Uani 1.000000 .
C8 C 0.0002(3) -0.13988(16) -0.34190(9) 0.0148(3) Uani 1.000000 .
C14 C 0.3597(3) -0.03800(15) -0.33833(10) 0.0180(4) Uani 1.000000 .
H14a H 0.4974(8) -0.0463(5) -0.3185(7) 0.0270(5) Uiso 1.000000 GR
H14b H 0.367(2) -0.0251(7) -0.39168(11) 0.0270(5) Uiso 1.000000 GR
H14c H 0.2926(13) 0.0277(3) -0.3148(7) 0.0270(5) Uiso 1.000000 GR
C7 C 0.2365(3) -0.14960(16) -0.32254(9) 0.0143(3) Uani 1.000000 .
C13 C 0.3278(3) -0.29206(16) -0.20964(10) 0.0177(4) Uani 1.000000 .
H13a H 0.2746(16) -0.3581(2) -0.2372(6) 0.0265(5) Uiso 1.000000 GR
H13b H 0.4737(4) -0.2843(5) -0.2191(8) 0.0265(5) Uiso 1.000000 GR
H13c H 0.3053(19) -0.3041(7) -0.15679(19) 0.0265(5) Uiso 1.000000 GR
C12 C -0.0853(4) -0.13142(18) -0.01431(10) 0.0247(4) Uani 1.000000 .
H12a H 0.0044(15) -0.1716(13) 0.02029(18) 0.0371(6) Uiso 1.000000 GR
H12b H -0.096(3) -0.05017(19) -0.0001(4) 0.0371(6) Uiso 1.000000 GR
H12c H -0.2204(12) -0.1668(14) -0.0131(3) 0.0371(6) Uiso 1.000000 GR
C11 C 0.3117(3) -0.25655(16) -0.36877(10) 0.0171(4) Uani 1.000000 .
H11 H 0.4227(3) -0.29703(16) -0.34139(10) 0.0205(4) Uiso 1.000000 R
C15 C -0.0657(3) -0.06438(17) -0.40818(10) 0.0190(4) Uani 1.000000 .
H15a H -0.0340(3) 0.01733(17) -0.39751(10) 0.0228(4) Uiso 1.000000 R
H15b H -0.2144(3) -0.07112(17) -0.41517(10) 0.0228(4) Uiso 1.000000 R
C9 C -0.0631(3) -0.27069(15) -0.34379(10) 0.0164(4) Uani 1.000000 .
H9 H -0.1898(3) -0.28355(15) -0.37310(10) 0.0197(4) Uiso 1.000000 R
C10 C 0.1209(3) -0.33878(16) -0.37560(10) 0.0189(4) Uani 1.000000 .
H10a H 0.0963(3) -0.35928(16) -0.42785(10) 0.0227(5) Uiso 1.000000 R
H10b H 0.1431(3) -0.41055(16) -0.34720(10) 0.0227(5) Uiso 1.000000 R


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 C0aa 1.434(2) . ?
O1 C8 1.430(2) . ?
O3 H3 0.8200 . ?
O3 C11 1.441(2) . ?
O2 C0aa 1.427(2) . ?
O2 C9 1.455(2) . ?
C1 H1 0.9300 . ?
C1 C0aa 1.485(2) . ?
C1 C2 1.323(3) . ?
C0aa C6 1.545(2) . ?
C2 C3 1.509(3) . ?
C2 C12 1.502(2) . ?
C3 H3a 0.9700 . ?
C3 H3b 0.9700 . ?
C3 C5 1.534(2) . ?
O4 H4 0.8200 . ?
O4 C15 1.431(2) . ?
C5 H5a 0.9700 . ?
C5 H5b 0.9700 . ?
C5 C6 1.546(2) . ?
C6 C7 1.603(2) . ?
C6 C13 1.528(2) . ?
C8 C7 1.566(2) . ?
C8 C15 1.518(2) . ?
C8 C9 1.543(2) . ?
C14 H14a 0.9600 . ?
C14 H14b 0.9600 . ?
C14 H14c 0.9600 . ?
C14 C7 1.523(2) . ?
C7 C11 1.546(2) . ?
C13 H13a 0.9600 . ?
C13 H13b 0.9600 . ?
C13 H13c 0.9600 . ?
C12 H12a 0.9600 . ?
C12 H12b 0.9600 . ?
C12 H12c 0.9600 . ?
C11 H11 0.9800 . ?
C11 C10 1.550(2) . ?
C15 H15a 0.9700 . ?
C15 H15b 0.9700 . ?
C9 H9 0.9800 . ?
C9 C10 1.526(2) . ?
C10 H10a 0.9700 . ?
C10 H10b 0.9700 . ?

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
C8 O1 C0aa 95.70(13) . . ?
C11 O3 H3 109.5 . . ?
C9 O2 C0aa 104.51(12) . . ?
C0aa C1 H1 118.68(10) . . ?
C2 C1 H1 118.68(11) . . ?
C2 C1 C0aa 122.65(17) . . ?
O2 C0aa O1 103.04(13) . . ?
C1 C0aa O1 112.58(14) . . ?
C1 C0aa O2 110.74(14) . . ?
C6 C0aa O1 103.15(14) . . ?
C6 C0aa O2 110.27(14) . . ?
C6 C0aa C1 116.07(15) . . ?
C3 C2 C1 122.17(16) . . ?
C12 C2 C1 122.25(17) . . ?
C12 C2 C3 115.57(16) . . ?
H3a C3 C2 108.85(10) . . ?
H3b C3 C2 108.85(10) . . ?
H3b C3 H3a 107.7 . . ?
C5 C3 C2 113.57(15) . . ?
C5 C3 H3a 108.85(9) . . ?
C5 C3 H3b 108.85(10) . . ?
C15 O4 H4 109.5 . . ?
H5a C5 C3 109.24(10) . . ?
H5b C5 C3 109.24(10) . . ?
H5b C5 H5a 107.9 . . ?
C6 C5 C3 111.88(14) . . ?
C6 C5 H5a 109.24(9) . . ?
C6 C5 H5b 109.24(9) . . ?
C5 C6 C0aa 106.53(14) . . ?
C7 C6 C0aa 100.57(13) . . ?
C7 C6 C5 111.90(13) . . ?
C13 C6 C0aa 112.21(14) . . ?
C13 C6 C5 109.76(14) . . ?
C13 C6 C7 115.28(14) . . ?
C7 C8 O1 105.44(13) . . ?
C15 C8 O1 109.72(14) . . ?
C15 C8 C7 118.85(15) . . ?
C9 C8 O1 102.88(13) . . ?
C9 C8 C7 101.19(14) . . ?
C9 C8 C15 117.02(14) . . ?
H14b C14 H14a 109.5 . . ?
H14c C14 H14a 109.5 . . ?
H14c C14 H14b 109.5 . . ?
C7 C14 H14a 109.5 . . ?
C7 C14 H14b 109.5 . . ?
C7 C14 H14c 109.5 . . ?
C8 C7 C6 98.60(13) . . ?
C14 C7 C6 113.75(14) . . ?
C14 C7 C8 114.09(15) . . ?
C11 C7 C6 111.80(14) . . ?
C11 C7 C8 104.14(14) . . ?
C11 C7 C14 113.20(14) . . ?
H13a C13 C6 109.5 . . ?
H13b C13 C6 109.5 . . ?
H13b C13 H13a 109.5 . . ?
H13c C13 C6 109.5 . . ?
H13c C13 H13a 109.5 . . ?
H13c C13 H13b 109.5 . . ?
H12a C12 C2 109.5 . . ?
H12b C12 C2 109.5 . . ?
H12b C12 H12a 109.5 . . ?
H12c C12 C2 109.5 . . ?
H12c C12 H12a 109.5 . . ?
H12c C12 H12b 109.5 . . ?
C7 C11 O3 111.92(15) . . ?
H11 C11 O3 109.57(9) . . ?
H11 C11 C7 109.57(9) . . ?
C10 C11 O3 110.65(14) . . ?
C10 C11 C7 105.48(14) . . ?
C10 C11 H11 109.57(10) . . ?
C8 C15 O4 111.42(15) . . ?
H15a C15 O4 109.34(9) . . ?
H15a C15 C8 109.34(10) . . ?
H15b C15 O4 109.34(9) . . ?
H15b C15 C8 109.34(10) . . ?
H15b C15 H15a 108.0 . . ?
C8 C9 O2 101.15(13) . . ?
H9 C9 O2 112.09(8) . . ?
H9 C9 C8 112.09(9) . . ?
C10 C9 O2 111.86(15) . . ?
C10 C9 C8 106.96(14) . . ?
C10 C9 H9 112.09(9) . . ?
C9 C10 C11 106.40(13) . . ?
H10a C10 C11 110.45(9) . . ?
H10a C10 C9 110.45(10) . . ?
H10b C10 C11 110.45(10) . . ?
H10b C10 C9 110.45(10) . . ?
H10b C10 H10a 108.6 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_exptl_crystal_recrystallization_method 'Vapour deposition'
