# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2015

####################################################################### 
# 
# 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_zhaogaoyuan0423
_database_code_depnum_ccdc_archive 'CCDC 1041808'
_audit_update_record             
;
2015-04-13 deposited with the CCDC.
2015-10-06 downloaded from the CCDC.
;
_audit_creation_date             2013-04-26
_audit_creation_method           
;
  Olex2 1.2
  (compiled Apr 23 2013 17:54:37, GUI svn.r4466)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C13 H16 O3'
_chemical_formula_sum            'C26 H32 O6'
_chemical_formula_weight         440.52
_chemical_absolute_configuration unk
_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                   7.7711(3)
_cell_length_b                   11.0137(3)
_cell_length_c                   12.6885(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1086.00(6)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4678
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      70.7170
_cell_measurement_theta_min      5.2990
_exptl_absorpt_coefficient_mu    1.540
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.58965
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_density_diffrn    2.694
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             944
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0444
_diffrn_reflns_av_unetI/netI     0.0351
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            6032
_diffrn_reflns_theta_full        70.06
_diffrn_reflns_theta_max         70.06
_diffrn_reflns_theta_min         5.32
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 16.0733
_diffrn_measured_fraction_theta_full 0.9555
_diffrn_measured_fraction_theta_max 0.9755
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -82.00  -57.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000  178.0000   90.0000 25

#__ type_ start__ end____ width___ exp.time_
  2 omega  -82.00  -57.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000  178.0000    0.0000 25

#__ type_ start__ end____ width___ exp.time_
  3 omega  -82.00  -51.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000  178.0000 -150.0000 31

#__ type_ start__ end____ width___ exp.time_
  4 omega  -41.00  -10.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -42.5000   38.0000 -150.0000 31

#__ type_ start__ end____ width___ exp.time_
  5 omega -123.00  -71.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -42.5000  178.0000 -150.0000 52

#__ type_ start__ end____ width___ exp.time_
  6 omega    6.00   32.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       56.0000  -99.0000 -120.0000 26

#__ type_ start__ end____ width___ exp.time_
  7 omega   24.00  113.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       56.0000 -125.0000 -150.0000 89

#__ type_ start__ end____ width___ exp.time_
  8 omega   80.00  128.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       56.0000   38.0000   60.0000 48

#__ type_ start__ end____ width___ exp.time_
  9 omega   76.00  101.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       56.0000  -99.0000 -120.0000 25

#__ type_ start__ end____ width___ exp.time_
 10 omega   86.00  135.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  178.0000   90.0000 49

#__ type_ start__ end____ width___ exp.time_
 11 omega   52.00  113.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000 -111.0000  -60.0000 61

#__ type_ start__ end____ width___ exp.time_
 12 omega   40.00   77.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -38.0000   30.0000 37

#__ type_ start__ end____ width___ exp.time_
 13 omega   51.00   91.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -38.0000  120.0000 40

#__ type_ start__ end____ width___ exp.time_
 14 omega   85.00  125.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   12.0000  -90.0000 40

#__ type_ start__ end____ width___ exp.time_
 15 omega   50.00   76.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   12.0000  -90.0000 26

#__ type_ start__ end____ width___ exp.time_
 16 omega   42.00   76.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -25.0000  -60.0000 34

#__ type_ start__ end____ width___ exp.time_
 17 omega   39.00   91.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -38.0000 -180.0000 52

#__ type_ start__ end____ width___ exp.time_
 18 omega   49.00  143.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -77.0000   30.0000 94

#__ type_ start__ end____ width___ exp.time_
 19 omega    2.00   27.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -42.5000   63.0000  120.0000 25

#__ type_ start__ end____ width___ exp.time_
 20 omega  -72.00   33.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000  -77.0000 -180.0000 105

#__ type_ start__ end____ width___ exp.time_
 21 omega  -24.00   35.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000  -81.0000  -92.0000 59

#__ type_ start__ end____ width___ exp.time_
 22 omega   32.00  127.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       56.0000   57.0000 -180.0000 95

#__ type_ start__ end____ width___ exp.time_
 23 omega   26.00  128.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       56.0000   72.0000 -103.6278 102

#__ type_ start__ end____ width___ exp.time_
 24 omega   23.00  128.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       56.0000   77.0000   90.0000 105

#__ type_ start__ end____ width___ exp.time_
 25 omega   32.00  127.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       56.0000   57.0000    0.0000 95

#__ type_ start__ end____ width___ exp.time_
 26 omega  153.00  178.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   77.0000 -180.0000 25

#__ type_ start__ end____ width___ exp.time_
 27 omega   79.00  117.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  178.0000  -90.0000 38

#__ type_ start__ end____ width___ exp.time_
 28 omega   49.00   75.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -25.0000 -150.0000 26

#__ type_ start__ end____ width___ exp.time_
 29 omega   67.00   93.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -50.0000  150.0000 26

#__ type_ start__ end____ width___ exp.time_
 30 omega   51.00   92.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -50.0000 -120.0000 41

#__ type_ start__ end____ width___ exp.time_
 31 omega  116.00  161.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   50.0000  150.0000 45

#__ type_ start__ end____ width___ exp.time_
 32 omega   65.00  100.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000 -111.0000    0.0000 35

#__ type_ start__ end____ width___ exp.time_
 33 omega   71.00   97.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   25.0000   60.0000 26

#__ type_ start__ end____ width___ exp.time_
 34 omega   80.00  105.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   77.0000 -180.0000 25
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.1460852000
_diffrn_orient_matrix_UB_12      -0.0485595000
_diffrn_orient_matrix_UB_13      -0.0709328000
_diffrn_orient_matrix_UB_21      -0.0902340000
_diffrn_orient_matrix_UB_22      -0.1250955000
_diffrn_orient_matrix_UB_23      -0.0055704000
_diffrn_orient_matrix_UB_31      -0.0997974000
_diffrn_orient_matrix_UB_32      0.0419760000
_diffrn_orient_matrix_UB_33      -0.0985587000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.5418
_diffrn_source                   'SuperNova (Cu) X-ray Source'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                1953
_reflns_number_total             2029
_reflns_odcompleteness_completeness 95.55
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     74.33
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_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, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution    'SUPERFLIP, J. Appl. Cryst. (2007) 40, 786-790'
_refine_diff_density_max         0.202
_refine_diff_density_min         -0.204
_refine_diff_density_rms         0.041
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.0(3)
_refine_ls_extinction_coef       0.045(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.065
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     147
_refine_ls_number_reflns         2029
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0433
_refine_ls_R_factor_gt           0.0422
_refine_ls_restrained_S_all      1.065
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0579P)²+0.3486P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1101
_refine_ls_wR_factor_ref         0.1112
_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. 
;
_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 O(H) groups
2.a Ternary CH refined with riding coordinates:
 C1(H1), C5(H5), C6(H6), C9(H9), C11(H11), C12(H12), C13(H13)
2.b Secondary CH2 refined with riding coordinates:
 C4(H4A,H4B), C7(H7A,H7B), C8(H8A,H8B)
2.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3A)
2.d Idealised tetrahedral OH refined as rotating group:
 O3(H3)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_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 0.12266(17) -0.44967(13) -0.32639(10) 0.0284(4) Uani 1 1 d . . .
O2 O 0.1129(2) -0.52246(16) -0.16653(12) 0.0451(5) Uani 1 1 d . . .
O3 O 0.1081(2) -0.61794(15) -0.57810(12) 0.0398(4) Uani 1 1 d . . .
H3 H 0.1919 -0.5856 -0.6056 0.060 Uiso 1 1 calc R . .
C1 C -0.0916(2) -0.43629(17) -0.47047(14) 0.0237(4) Uani 1 1 d . . .
H1 H -0.0903 -0.4229 -0.5468 0.028 Uiso 1 1 calc R . .
C2 C -0.1698(3) -0.32491(19) -0.42337(15) 0.0295(5) Uani 1 1 d . . .
H2 H -0.1011 -0.2569 -0.4126 0.035 Uiso 1 1 calc R . .
C3 C -0.3342(3) -0.3205(2) -0.39654(17) 0.0356(5) Uani 1 1 d . . .
H3A H -0.3797 -0.2478 -0.3717 0.043 Uiso 1 1 calc R . .
C4 C -0.4493(3) -0.4296(2) -0.40512(17) 0.0371(5) Uani 1 1 d . . .
H4A H -0.4962 -0.4342 -0.4759 0.044 Uiso 1 1 calc R . .
H4B H -0.5446 -0.4212 -0.3563 0.044 Uiso 1 1 calc R . .
C5 C -0.3502(2) -0.5475(2) -0.38046(15) 0.0287(4) Uani 1 1 d . . .
H5 H -0.4265 -0.6159 -0.3965 0.034 Uiso 1 1 calc R . .
C6 C -0.1917(2) -0.55800(18) -0.45262(14) 0.0245(4) Uani 1 1 d . . .
H6 H -0.2328 -0.5852 -0.5217 0.029 Uiso 1 1 calc R . .
C7 C -0.3076(3) -0.5530(2) -0.26286(15) 0.0310(5) Uani 1 1 d . . .
H7A H -0.2509 -0.4783 -0.2421 0.037 Uiso 1 1 calc R . .
H7B H -0.4136 -0.5596 -0.2229 0.037 Uiso 1 1 calc R . .
C8 C -0.1916(3) -0.6601(2) -0.23619(15) 0.0313(5) Uani 1 1 d . . .
H8A H -0.2484 -0.7354 -0.2551 0.038 Uiso 1 1 calc R . .
H8B H -0.1689 -0.6615 -0.1610 0.038 Uiso 1 1 calc R . .
C9 C -0.0216(3) -0.64847(19) -0.29698(15) 0.0271(5) Uani 1 1 d . . .
H9 H 0.0486 -0.7197 -0.2796 0.032 Uiso 1 1 calc R . .
C10 C 0.0752(3) -0.5367(2) -0.25837(15) 0.0280(4) Uani 1 1 d . . .
C11 C 0.0944(2) -0.46528(18) -0.43926(14) 0.0255(4) Uani 1 1 d . . .
H11 H 0.1754 -0.4157 -0.4799 0.031 Uiso 1 1 calc R . .
C12 C -0.0503(2) -0.64904(18) -0.41698(15) 0.0256(4) Uani 1 1 d . . .
H12 H -0.0755 -0.7312 -0.4424 0.031 Uiso 1 1 calc R . .
C13 C 0.1138(3) -0.59944(19) -0.46731(16) 0.0298(5) Uani 1 1 d . . .
H13 H 0.2173 -0.6350 -0.4358 0.036 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 C10 1.342(2) . ?
O1 C11 1.459(2) . ?
O2 C10 1.212(2) . ?
O3 C13 1.421(2) . ?
C1 C2 1.494(3) . ?
C1 C6 1.566(3) . ?
C1 C11 1.533(3) . ?
C2 C3 1.323(3) . ?
C3 C4 1.502(4) . ?
C4 C5 1.541(3) . ?
C5 C6 1.539(3) . ?
C5 C7 1.530(3) . ?
C6 C12 1.554(3) . ?
C7 C8 1.522(3) . ?
C8 C9 1.535(3) . ?
C9 C10 1.523(3) . ?
C9 C12 1.539(3) . ?
C11 C13 1.527(3) . ?
C12 C13 1.527(3) . ?

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
C10 O1 C11 120.39(16) . . ?
C2 C1 C6 116.32(15) . . ?
C2 C1 C11 116.83(16) . . ?
C11 C1 C6 104.63(15) . . ?
C3 C2 C1 121.7(2) . . ?
C2 C3 C4 121.8(2) . . ?
C3 C4 C5 111.18(16) . . ?
C6 C5 C4 110.05(17) . . ?
C7 C5 C4 109.88(17) . . ?
C7 C5 C6 113.83(15) . . ?
C5 C6 C1 114.75(17) . . ?
C5 C6 C12 116.18(16) . . ?
C12 C6 C1 104.09(15) . . ?
C8 C7 C5 112.09(17) . . ?
C7 C8 C9 109.45(16) . . ?
C8 C9 C12 111.84(16) . . ?
C10 C9 C8 109.31(17) . . ?
C10 C9 C12 113.14(16) . . ?
O1 C10 C9 120.41(16) . . ?
O2 C10 O1 117.4(2) . . ?
O2 C10 C9 122.23(19) . . ?
O1 C11 C1 111.78(15) . . ?
O1 C11 C13 109.14(15) . . ?
C13 C11 C1 103.55(16) . . ?
C9 C12 C6 112.81(15) . . ?
C13 C12 C6 103.75(16) . . ?
C13 C12 C9 106.93(16) . . ?
O3 C13 C11 111.48(17) . . ?
O3 C13 C12 109.66(17) . . ?
C12 C13 C11 99.57(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 
# 
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# Please retain this information to preserve the provenance of 
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data_zhaogy1023
_database_code_depnum_ccdc_archive 'CCDC 1041809'
_audit_update_record             
;
2015-04-13 deposited with the CCDC.
2015-10-06 downloaded from the CCDC.
;
_audit_creation_date             2013-10-30
_audit_creation_method           
;
Olex2 1.2
(compiled 2013.09.17 svn.r2790 for OlexSys, GUI svn.r4601)
;
_shelxl_version_number           2013-2
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C14 H20 O3'
_chemical_formula_sum            'C14 H20 O3'
_chemical_formula_weight         236.30
_chemical_absolute_configuration ?
_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           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                   15.8905(18)
_cell_length_b                   6.1745(5)
_cell_length_c                   19.186(4)
_cell_angle_alpha                90
_cell_angle_beta                 104.581(16)
_cell_angle_gamma                90
_cell_volume                     1821.8(4)
_cell_formula_units_Z            6
_cell_measurement_reflns_used    1020
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      25.7090
_cell_measurement_theta_min      3.5500
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.089
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.49560
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_density_diffrn    1.292
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             768
_exptl_crystal_size_max          0.2400
_exptl_crystal_size_mid          0.1200
_exptl_crystal_size_min          0.1000
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0633
_diffrn_reflns_av_unetI/netI     0.1352
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            7814
_diffrn_reflns_point_group_measured_fraction_full 0.827
_diffrn_reflns_point_group_measured_fraction_max 0.815
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.022
_diffrn_reflns_theta_min         2.984
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 16.0733
_diffrn_measured_fraction_theta_full 0.9976
_diffrn_measured_fraction_theta_max 0.7104
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0452578000
_diffrn_orient_matrix_UB_12      0.0048858000
_diffrn_orient_matrix_UB_13      0.0164453000
_diffrn_orient_matrix_UB_21      -0.0088931000
_diffrn_orient_matrix_UB_22      0.0067263000
_diffrn_orient_matrix_UB_23      0.0343424000
_diffrn_orient_matrix_UB_31      0.0014064000
_diffrn_orient_matrix_UB_32      -0.1145882000
_diffrn_orient_matrix_UB_33      0.0027051000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_reflns_Friedel_coverage         0.487
_reflns_Friedel_fraction_full    0.619
_reflns_Friedel_fraction_max     0.592
_reflns_number_gt                2809
_reflns_number_total             5859
_reflns_odcompleteness_completeness 99.76
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_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  
;
SHELX, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution    'SUPERFLIP, J. Appl. Cryst. (2007) 40, 786-790'
_refine_diff_density_max         0.200
_refine_diff_density_min         -0.207
_refine_diff_density_rms         0.048
_refine_ls_abs_structure_details 
;
 Flack x determined using 702 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   3.9(10)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     466
_refine_ls_number_reflns         5859
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.1558
_refine_ls_R_factor_gt           0.0739
_refine_ls_restrained_S_all      1.036
_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)+(0.0363P)²]
 where P=(Fo²+2Fc²)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1263
_refine_ls_wR_factor_ref         0.1775
_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:
 C1(H1A), C4(H4), C5(H5), C6(H6), C7(H7), C8(H8), C9(H9), C10(H10), C15(H15),
 C18(H18), C19(H19), C20(H20), C23(H23), C24(H24), C25(H25), C26(H26), C28(H28),
  C31(H31), C32(H32), C33(H33), C36(H36), C37(H37), C39(H39), C42(H42)
2.b Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C3(H3A,H3B), C11(H11A,H11B), C12(H12A,H12B), C16(H16A,H16B),
 C17(H17A,H17B), C21(H21A,H21B), C22(H22A,H22B), C29(H29A,H29B), C30(H30A,H30B),
  C34(H34A,H34B), C35(H35A,H35B)
2.c Idealised Me refined as rotating group:
 C1E(H1EA,H1EB,H1EC), C14(H14A,H14B,H14C), C40(H40A,H40B,H40C)
2.d Idealised tetrahedral OH refined as rotating group:
 O1(H1), O6(H6A), O8(H8A)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_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 -0.2067(4) -0.1998(10) -0.6866(4) 0.0745(19) Uani 1 1 d . . . . .
H1 H -0.2462 -0.2109 -0.7233 0.112 Uiso 1 1 calc R U . . .
O2 O -0.1154(3) -0.2041(9) -0.5454(4) 0.0593(17) Uani 1 1 d . . . . .
O3 O -0.1083(5) -0.1313(11) -0.4315(4) 0.085(2) Uani 1 1 d . . . . .
O4 O -0.1953(3) -0.6588(9) -0.8292(3) 0.0596(17) Uani 1 1 d . . . . .
O5 O -0.2357(4) -0.3529(10) -0.8906(3) 0.0649(17) Uani 1 1 d . . . . .
O6 O -0.0992(4) -0.8707(10) -0.7035(3) 0.074(2) Uani 1 1 d . . . . .
H6A H -0.1370 -0.9561 -0.6991 0.111 Uiso 1 1 calc R U . . .
O7 O -0.5032(4) -0.6699(10) -1.0796(3) 0.0669(17) Uani 1 1 d . . . . .
O8 O -0.6514(4) -0.7382(10) -1.1937(4) 0.0718(19) Uani 1 1 d . . . . .
H8A H -0.6762 -0.7714 -1.1626 0.108 Uiso 1 1 calc R U . . .
O9 O -0.3642(5) -0.7294(12) -1.0309(4) 0.090(2) Uani 1 1 d . . . . .
C1 C -0.3596(5) -0.7094(13) -0.5446(5) 0.052(2) Uani 1 1 d . . . . .
H1A H -0.3719 -0.7928 -0.5895 0.063 Uiso 1 1 calc R U . . .
C1E C 0.1792(6) -0.3584(16) -0.8453(6) 0.080(3) Uani 1 1 d . . . . .
H1EA H 0.1523 -0.2185 -0.8539 0.120 Uiso 1 1 calc R U . . .
H1EB H 0.1930 -0.4092 -0.8884 0.120 Uiso 1 1 calc R U . . .
H1EC H 0.2316 -0.3478 -0.8073 0.120 Uiso 1 1 calc R U . . .
C2 C -0.3851(5) -0.4721(13) -0.5643(5) 0.059(2) Uani 1 1 d . . . . .
H2A H -0.3951 -0.3990 -0.5224 0.071 Uiso 1 1 calc R U . . .
H2B H -0.4391 -0.4694 -0.6017 0.071 Uiso 1 1 calc R U . . .
C3 C -0.3142(5) -0.3469(12) -0.5911(5) 0.053(2) Uani 1 1 d . . . . .
H3A H -0.3415 -0.2398 -0.6267 0.064 Uiso 1 1 calc R U . . .
H3B H -0.2758 -0.2721 -0.5511 0.064 Uiso 1 1 calc R U . . .
C4 C -0.2622(5) -0.5055(11) -0.6243(4) 0.045(2) Uani 1 1 d . . . . .
H4 H -0.3023 -0.5826 -0.6637 0.054 Uiso 1 1 calc R U . . .
C5 C -0.2144(5) -0.6732(12) -0.5685(4) 0.045(2) Uani 1 1 d . . . . .
H5 H -0.2123 -0.8078 -0.5950 0.054 Uiso 1 1 calc R U . . .
C6 C -0.2619(5) -0.7273(13) -0.5096(4) 0.051(2) Uani 1 1 d . . . . .
H6 H -0.2498 -0.8798 -0.4968 0.061 Uiso 1 1 calc R U . . .
C7 C -0.1886(6) -0.4082(15) -0.6531(5) 0.061(3) Uani 1 1 d . . . . .
H7 H -0.1750 -0.5091 -0.6882 0.073 Uiso 1 1 calc R U . . .
C8 C -0.1109(6) -0.3945(15) -0.5891(5) 0.062(3) Uani 1 1 d . . . . .
H8 H -0.0564 -0.3977 -0.6043 0.075 Uiso 1 1 calc R U . . .
C9 C -0.1181(5) -0.5910(13) -0.5420(5) 0.054(2) Uani 1 1 d . . . . .
H9 H -0.0779 -0.7048 -0.5487 0.064 Uiso 1 1 calc R U . . .
C10 C -0.0890(6) -0.4996(13) -0.4661(5) 0.057(2) Uani 1 1 d . . . . .
H10 H -0.0262 -0.5218 -0.4486 0.068 Uiso 1 1 calc R U . . .
C11 C -0.1330(6) -0.5975(15) -0.4113(5) 0.069(3) Uani 1 1 d . . . . .
H11A H -0.1131 -0.7452 -0.4008 0.082 Uiso 1 1 calc R U . . .
H11B H -0.1171 -0.5152 -0.3669 0.082 Uiso 1 1 calc R U . . .
C12 C -0.2308(6) -0.5957(13) -0.4400(4) 0.057(2) Uani 1 1 d . . . . .
H12A H -0.2503 -0.4472 -0.4491 0.068 Uiso 1 1 calc R U . . .
H12B H -0.2571 -0.6543 -0.4037 0.068 Uiso 1 1 calc R U . . .
C13 C -0.1056(6) -0.2627(14) -0.4762(6) 0.061(3) Uani 1 1 d . . . . .
C14 C -0.4159(6) -0.8033(16) -0.4974(6) 0.089(4) Uani 1 1 d . . . . .
H14A H -0.4039 -0.7271 -0.4523 0.133 Uiso 1 1 calc R U . . .
H14B H -0.4026 -0.9541 -0.4887 0.133 Uiso 1 1 calc R U . . .
H14C H -0.4762 -0.7873 -0.5216 0.133 Uiso 1 1 calc R U . . .
C15 C 0.1168(5) -0.5173(14) -0.8232(5) 0.057(2) Uani 1 1 d . . . . .
H15 H 0.1503 -0.6502 -0.8086 0.068 Uiso 1 1 calc R U . . .
C16 C 0.0891(5) -0.4409(14) -0.7574(5) 0.060(2) Uani 1 1 d . . . . .
H16A H 0.0791 -0.2859 -0.7614 0.072 Uiso 1 1 calc R U . . .
H16B H 0.1366 -0.4660 -0.7152 0.072 Uiso 1 1 calc R U . . .
C17 C 0.0066(6) -0.5513(12) -0.7455(5) 0.055(2) Uani 1 1 d . . . . .
H17A H 0.0097 -0.5596 -0.6944 0.066 Uiso 1 1 calc R U . . .
H17B H -0.0446 -0.4680 -0.7687 0.066 Uiso 1 1 calc R U . . .
C18 C 0.0007(5) -0.7747(12) -0.7772(4) 0.048(2) Uani 1 1 d . . . . .
H18 H 0.0532 -0.8545 -0.7528 0.058 Uiso 1 1 calc R U . . .
C19 C -0.0058(5) -0.7771(12) -0.8595(4) 0.047(2) Uani 1 1 d . . . . .
H19 H 0.0258 -0.9062 -0.8685 0.056 Uiso 1 1 calc R U . . .
C20 C 0.0394(5) -0.5832(12) -0.8843(5) 0.048(2) Uani 1 1 d . . . . .
H20 H 0.0621 -0.6316 -0.9247 0.058 Uiso 1 1 calc R U . . .
C21 C -0.0218(5) -0.3914(13) -0.9109(4) 0.049(2) Uani 1 1 d . . . . .
H21A H -0.0400 -0.3293 -0.8706 0.059 Uiso 1 1 calc R U . . .
H21B H 0.0091 -0.2805 -0.9303 0.059 Uiso 1 1 calc R U . . .
C22 C -0.1021(5) -0.4623(13) -0.9689(5) 0.058(2) Uani 1 1 d . . . . .
H22A H -0.1383 -0.3373 -0.9863 0.069 Uiso 1 1 calc R U . . .
H22B H -0.0841 -0.5250 -1.0093 0.069 Uiso 1 1 calc R U . . .
C23 C -0.1541(5) -0.6288(13) -0.9381(5) 0.054(2) Uani 1 1 d . . . . .
H23 H -0.1987 -0.6884 -0.9784 0.065 Uiso 1 1 calc R U . . .
C24 C -0.1035(5) -0.8176(13) -0.8976(5) 0.053(2) Uani 1 1 d . . . . .
H24 H -0.1091 -0.9442 -0.9292 0.064 Uiso 1 1 calc R U . . .
C25 C -0.1492(5) -0.8604(13) -0.8372(5) 0.056(2) Uani 1 1 d . . . . .
H25 H -0.1898 -0.9824 -0.8493 0.068 Uiso 1 1 calc R U . . .
C26 C -0.0786(6) -0.9072(14) -0.7705(5) 0.062(3) Uani 1 1 d . . . . .
H26 H -0.0633 -1.0605 -0.7721 0.074 Uiso 1 1 calc R U . . .
C27 C -0.1998(6) -0.5304(14) -0.8861(5) 0.057(2) Uani 1 1 d . . . . .
C28 C -0.4274(6) -0.3178(14) -1.2879(5) 0.061(2) Uani 1 1 d . . . . .
H28 H -0.4787 -0.2436 -1.3172 0.073 Uiso 1 1 calc R U . . .
C29 C -0.4471(6) -0.5609(14) -1.2965(5) 0.068(3) Uani 1 1 d . . . . .
H29A H -0.4782 -0.5897 -1.3460 0.082 Uiso 1 1 calc R U . . .
H29B H -0.3926 -0.6401 -1.2869 0.082 Uiso 1 1 calc R U . . .
C30 C -0.5010(5) -0.6444(13) -1.2464(4) 0.056(2) Uani 1 1 d . . . . .
H30A H -0.5367 -0.7649 -1.2691 0.067 Uiso 1 1 calc R U . . .
H30B H -0.4624 -0.6963 -1.2020 0.067 Uiso 1 1 calc R U . . .
C31 C -0.5585(5) -0.4675(13) -1.2296(5) 0.052(2) Uani 1 1 d . . . . .
H31 H -0.5962 -0.4165 -1.2752 0.062 Uiso 1 1 calc R U . . .
C32 C -0.5056(5) -0.2710(13) -1.1914(5) 0.054(2) Uani 1 1 d . . . . .
H32 H -0.5403 -0.1418 -1.2088 0.064 Uiso 1 1 calc R U . . .
C33 C -0.4171(5) -0.2397(12) -1.2108(4) 0.048(2) Uani 1 1 d . . . . .
H33 H -0.4054 -0.0838 -1.2100 0.058 Uiso 1 1 calc R U . . .
C34 C -0.3410(5) -0.3465(14) -1.1577(5) 0.059(2) Uani 1 1 d . . . . .
H34A H -0.3472 -0.5026 -1.1616 0.071 Uiso 1 1 calc R U . . .
H34B H -0.2873 -0.3072 -1.1698 0.071 Uiso 1 1 calc R U . . .
C35 C -0.3361(6) -0.2795(16) -1.0817(5) 0.071(3) Uani 1 1 d . . . . .
H35A H -0.3323 -0.1230 -1.0778 0.085 Uiso 1 1 calc R U . . .
H35B H -0.2843 -0.3404 -1.0497 0.085 Uiso 1 1 calc R U . . .
C36 C -0.4157(6) -0.3579(15) -1.0598(5) 0.061(2) Uani 1 1 d . . . . .
H36 H -0.4137 -0.2954 -1.0124 0.073 Uiso 1 1 calc R U . . .
C37 C -0.5030(6) -0.2921(14) -1.1107(5) 0.062(3) Uani 1 1 d . . . . .
H37 H -0.5246 -0.1589 -1.0935 0.074 Uiso 1 1 calc R U . . .
C39 C -0.6157(6) -0.5236(15) -1.1798(5) 0.063(3) Uani 1 1 d . . . . .
H39 H -0.6644 -0.4211 -1.1894 0.075 Uiso 1 1 calc R U . . .
C40 C -0.3506(6) -0.2495(18) -1.3186(5) 0.094(4) Uani 1 1 d . . . . .
H40A H -0.3001 -0.3330 -1.2961 0.141 Uiso 1 1 calc R U . . .
H40B H -0.3386 -0.0985 -1.3092 0.141 Uiso 1 1 calc R U . . .
H40C H -0.3653 -0.2746 -1.3696 0.141 Uiso 1 1 calc R U . . .
C41 C -0.4202(7) -0.5983(18) -1.0527(5) 0.066(3) Uani 1 1 d . . . . .
C42 C -0.5622(6) -0.4842(15) -1.1037(5) 0.067(3) Uani 1 1 d . . . . .
H42 H -0.5985 -0.4531 -1.0705 0.081 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 H1 0.8200 . ?
O1 C7 1.434(10) . ?
O2 C8 1.457(10) . ?
O2 C13 1.347(11) . ?
O3 C13 1.189(10) . ?
O4 C25 1.471(9) . ?
O4 C27 1.336(10) . ?
O5 C27 1.229(9) . ?
O6 H6A 0.8200 . ?
O6 C26 1.422(9) . ?
O7 C41 1.364(10) . ?
O7 C42 1.480(11) . ?
O8 H8A 0.8200 . ?
O8 C39 1.440(10) . ?
O9 C41 1.198(11) . ?
C1 H1A 0.9800 . ?
C1 C2 1.542(11) . ?
C1 C6 1.533(10) . ?
C1 C14 1.537(10) . ?
C1E H1EA 0.9600 . ?
C1E H1EB 0.9600 . ?
C1E H1EC 0.9600 . ?
C1E C15 1.528(10) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C2 C3 1.556(10) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C3 C4 1.521(9) . ?
C4 H4 0.9800 . ?
C4 C5 1.545(10) . ?
C4 C7 1.536(10) . ?
C5 H5 0.9800 . ?
C5 C6 1.544(9) . ?
C5 C9 1.570(10) . ?
C6 H6 0.9800 . ?
C6 C12 1.534(11) . ?
C7 H7 0.9800 . ?
C7 C8 1.509(12) . ?
C8 H8 0.9800 . ?
C8 C9 1.535(11) . ?
C9 H9 0.9800 . ?
C9 C10 1.522(11) . ?
C10 H10 0.9800 . ?
C10 C11 1.526(12) . ?
C10 C13 1.491(11) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C11 C12 1.511(11) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C15 H15 0.9800 . ?
C15 C16 1.514(11) . ?
C15 C20 1.525(11) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C16 C17 1.545(10) . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C17 C18 1.501(10) . ?
C18 H18 0.9800 . ?
C18 C19 1.556(10) . ?
C18 C26 1.534(11) . ?
C19 H19 0.9800 . ?
C19 C20 1.533(10) . ?
C19 C24 1.561(11) . ?
C20 H20 0.9800 . ?
C20 C21 1.536(10) . ?
C21 H21A 0.9700 . ?
C21 H21B 0.9700 . ?
C21 C22 1.531(11) . ?
C22 H22A 0.9700 . ?
C22 H22B 0.9700 . ?
C22 C23 1.529(11) . ?
C23 H23 0.9800 . ?
C23 C24 1.514(11) . ?
C23 C27 1.503(11) . ?
C24 H24 0.9800 . ?
C24 C25 1.538(10) . ?
C25 H25 0.9800 . ?
C25 C26 1.502(12) . ?
C26 H26 0.9800 . ?
C28 H28 0.9800 . ?
C28 C29 1.534(12) . ?
C28 C33 1.525(10) . ?
C28 C40 1.540(10) . ?
C29 H29A 0.9700 . ?
C29 H29B 0.9700 . ?
C29 C30 1.529(10) . ?
C30 H30A 0.9700 . ?
C30 H30B 0.9700 . ?
C30 C31 1.511(10) . ?
C31 H31 0.9800 . ?
C31 C32 1.552(11) . ?
C31 C39 1.515(11) . ?
C32 H32 0.9800 . ?
C32 C33 1.554(9) . ?
C32 C37 1.544(11) . ?
C33 H33 0.9800 . ?
C33 C34 1.522(10) . ?
C34 H34A 0.9700 . ?
C34 H34B 0.9700 . ?
C34 C35 1.499(11) . ?
C35 H35A 0.9700 . ?
C35 H35B 0.9700 . ?
C35 C36 1.510(11) . ?
C36 H36 0.9800 . ?
C36 C37 1.537(12) . ?
C36 C41 1.494(13) . ?
C37 H37 0.9800 . ?
C37 C42 1.540(11) . ?
C39 H39 0.9800 . ?
C39 C42 1.512(12) . ?
C40 H40A 0.9600 . ?
C40 H40B 0.9600 . ?
C40 H40C 0.9600 . ?
C42 H42 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
C7 O1 H1 109.5 . . ?
C13 O2 C8 109.9(7) . . ?
C27 O4 C25 110.1(6) . . ?
C26 O6 H6A 109.5 . . ?
C41 O7 C42 110.1(8) . . ?
C39 O8 H8A 109.5 . . ?
C2 C1 H1A 107.6 . . ?
C6 C1 H1A 107.6 . . ?
C6 C1 C2 110.5(7) . . ?
C6 C1 C14 113.0(7) . . ?
C14 C1 H1A 107.6 . . ?
C14 C1 C2 110.3(7) . . ?
H1EA C1E H1EB 109.5 . . ?
H1EA C1E H1EC 109.5 . . ?
H1EB C1E H1EC 109.5 . . ?
C15 C1E H1EA 109.5 . . ?
C15 C1E H1EB 109.5 . . ?
C15 C1E H1EC 109.5 . . ?
C1 C2 H2A 109.0 . . ?
C1 C2 H2B 109.0 . . ?
C1 C2 C3 112.7(6) . . ?
H2A C2 H2B 107.8 . . ?
C3 C2 H2A 109.0 . . ?
C3 C2 H2B 109.0 . . ?
C2 C3 H3A 109.8 . . ?
C2 C3 H3B 109.8 . . ?
H3A C3 H3B 108.2 . . ?
C4 C3 C2 109.5(6) . . ?
C4 C3 H3A 109.8 . . ?
C4 C3 H3B 109.8 . . ?
C3 C4 H4 108.6 . . ?
C3 C4 C5 111.4(7) . . ?
C3 C4 C7 116.2(6) . . ?
C5 C4 H4 108.6 . . ?
C7 C4 H4 108.6 . . ?
C7 C4 C5 103.1(6) . . ?
C4 C5 H5 106.5 . . ?
C4 C5 C9 106.1(6) . . ?
C6 C5 C4 114.0(6) . . ?
C6 C5 H5 106.5 . . ?
C6 C5 C9 116.7(7) . . ?
C9 C5 H5 106.5 . . ?
C1 C6 C5 107.0(7) . . ?
C1 C6 H6 106.9 . . ?
C1 C6 C12 114.3(7) . . ?
C5 C6 H6 106.9 . . ?
C12 C6 C5 114.3(7) . . ?
C12 C6 H6 106.9 . . ?
O1 C7 C4 115.3(7) . . ?
O1 C7 H7 108.5 . . ?
O1 C7 C8 110.2(8) . . ?
C4 C7 H7 108.5 . . ?
C8 C7 C4 105.7(7) . . ?
C8 C7 H7 108.5 . . ?
O2 C8 C7 111.4(7) . . ?
O2 C8 H8 111.2 . . ?
O2 C8 C9 106.1(7) . . ?
C7 C8 H8 111.2 . . ?
C7 C8 C9 105.5(7) . . ?
C9 C8 H8 111.2 . . ?
C5 C9 H9 109.9 . . ?
C8 C9 C5 106.0(7) . . ?
C8 C9 H9 109.9 . . ?
C10 C9 C5 117.7(7) . . ?
C10 C9 C8 102.8(7) . . ?
C10 C9 H9 109.9 . . ?
C9 C10 H10 108.3 . . ?
C9 C10 C11 115.5(7) . . ?
C11 C10 H10 108.3 . . ?
C13 C10 C9 103.8(8) . . ?
C13 C10 H10 108.3 . . ?
C13 C10 C11 112.4(8) . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
H11A C11 H11B 108.1 . . ?
C12 C11 C10 110.7(8) . . ?
C12 C11 H11A 109.5 . . ?
C12 C11 H11B 109.5 . . ?
C6 C12 H12A 109.0 . . ?
C6 C12 H12B 109.0 . . ?
C11 C12 C6 112.9(7) . . ?
C11 C12 H12A 109.0 . . ?
C11 C12 H12B 109.0 . . ?
H12A C12 H12B 107.8 . . ?
O2 C13 C10 111.4(9) . . ?
O3 C13 O2 120.8(9) . . ?
O3 C13 C10 127.8(10) . . ?
C1 C14 H14A 109.5 . . ?
C1 C14 H14B 109.5 . . ?
C1 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C1E C15 H15 105.8 . . ?
C16 C15 C1E 112.1(8) . . ?
C16 C15 H15 105.8 . . ?
C16 C15 C20 112.1(6) . . ?
C20 C15 C1E 114.4(7) . . ?
C20 C15 H15 105.8 . . ?
C15 C16 H16A 108.5 . . ?
C15 C16 H16B 108.5 . . ?
C15 C16 C17 114.9(7) . . ?
H16A C16 H16B 107.5 . . ?
C17 C16 H16A 108.5 . . ?
C17 C16 H16B 108.5 . . ?
C16 C17 H17A 110.0 . . ?
C16 C17 H17B 110.0 . . ?
H17A C17 H17B 108.4 . . ?
C18 C17 C16 108.3(7) . . ?
C18 C17 H17A 110.0 . . ?
C18 C17 H17B 110.0 . . ?
C17 C18 H18 108.1 . . ?
C17 C18 C19 113.6(7) . . ?
C17 C18 C26 115.1(7) . . ?
C19 C18 H18 108.1 . . ?
C26 C18 H18 108.1 . . ?
C26 C18 C19 103.5(7) . . ?
C18 C19 H19 106.3 . . ?
C18 C19 C24 106.3(6) . . ?
C20 C19 C18 113.1(7) . . ?
C20 C19 H19 106.3 . . ?
C20 C19 C24 117.9(7) . . ?
C24 C19 H19 106.3 . . ?
C15 C20 C19 108.6(7) . . ?
C15 C20 H20 107.6 . . ?
C15 C20 C21 111.7(7) . . ?
C19 C20 H20 107.6 . . ?
C19 C20 C21 113.5(6) . . ?
C21 C20 H20 107.6 . . ?
C20 C21 H21A 109.4 . . ?
C20 C21 H21B 109.4 . . ?
H21A C21 H21B 108.0 . . ?
C22 C21 C20 111.3(7) . . ?
C22 C21 H21A 109.4 . . ?
C22 C21 H21B 109.4 . . ?
C21 C22 H22A 109.7 . . ?
C21 C22 H22B 109.7 . . ?
H22A C22 H22B 108.2 . . ?
C23 C22 C21 110.0(7) . . ?
C23 C22 H22A 109.7 . . ?
C23 C22 H22B 109.7 . . ?
C22 C23 H23 107.5 . . ?
C24 C23 C22 116.6(7) . . ?
C24 C23 H23 107.5 . . ?
C27 C23 C22 112.6(7) . . ?
C27 C23 H23 107.5 . . ?
C27 C23 C24 104.7(7) . . ?
C19 C24 H24 110.0 . . ?
C23 C24 C19 117.0(7) . . ?
C23 C24 H24 110.0 . . ?
C23 C24 C25 103.2(7) . . ?
C25 C24 C19 106.1(7) . . ?
C25 C24 H24 110.0 . . ?
O4 C25 C24 105.9(6) . . ?
O4 C25 H25 111.1 . . ?
O4 C25 C26 111.0(7) . . ?
C24 C25 H25 111.1 . . ?
C26 C25 C24 106.3(7) . . ?
C26 C25 H25 111.1 . . ?
O6 C26 C18 111.8(7) . . ?
O6 C26 C25 116.5(7) . . ?
O6 C26 H26 107.3 . . ?
C18 C26 H26 107.3 . . ?
C25 C26 C18 106.3(7) . . ?
C25 C26 H26 107.3 . . ?
O4 C27 C23 111.5(7) . . ?
O5 C27 O4 121.0(8) . . ?
O5 C27 C23 127.4(9) . . ?
C29 C28 H28 106.1 . . ?
C29 C28 C40 112.7(8) . . ?
C33 C28 H28 106.1 . . ?
C33 C28 C29 112.5(7) . . ?
C33 C28 C40 112.5(7) . . ?
C40 C28 H28 106.1 . . ?
C28 C29 H29A 108.9 . . ?
C28 C29 H29B 108.9 . . ?
H29A C29 H29B 107.8 . . ?
C30 C29 C28 113.2(7) . . ?
C30 C29 H29A 108.9 . . ?
C30 C29 H29B 108.9 . . ?
C29 C30 H30A 109.5 . . ?
C29 C30 H30B 109.5 . . ?
H30A C30 H30B 108.1 . . ?
C31 C30 C29 110.9(7) . . ?
C31 C30 H30A 109.5 . . ?
C31 C30 H30B 109.5 . . ?
C30 C31 H31 107.9 . . ?
C30 C31 C32 112.4(6) . . ?
C30 C31 C39 117.5(7) . . ?
C32 C31 H31 107.9 . . ?
C39 C31 H31 107.9 . . ?
C39 C31 C32 102.8(7) . . ?
C31 C32 H32 106.4 . . ?
C31 C32 C33 113.6(6) . . ?
C33 C32 H32 106.4 . . ?
C37 C32 C31 106.4(7) . . ?
C37 C32 H32 106.4 . . ?
C37 C32 C33 117.0(7) . . ?
C28 C33 C32 108.2(7) . . ?
C28 C33 H33 107.4 . . ?
C32 C33 H33 107.4 . . ?
C34 C33 C28 112.6(7) . . ?
C34 C33 C32 113.6(7) . . ?
C34 C33 H33 107.4 . . ?
C33 C34 H34A 109.3 . . ?
C33 C34 H34B 109.3 . . ?
H34A C34 H34B 107.9 . . ?
C35 C34 C33 111.7(7) . . ?
C35 C34 H34A 109.3 . . ?
C35 C34 H34B 109.3 . . ?
C34 C35 H35A 109.7 . . ?
C34 C35 H35B 109.7 . . ?
C34 C35 C36 109.9(7) . . ?
H35A C35 H35B 108.2 . . ?
C36 C35 H35A 109.7 . . ?
C36 C35 H35B 109.7 . . ?
C35 C36 H36 107.4 . . ?
C35 C36 C37 115.1(8) . . ?
C37 C36 H36 107.4 . . ?
C41 C36 C35 114.0(8) . . ?
C41 C36 H36 107.4 . . ?
C41 C36 C37 105.3(8) . . ?
C32 C37 H37 110.1 . . ?
C36 C37 C32 116.8(7) . . ?
C36 C37 H37 110.1 . . ?
C36 C37 C42 102.4(8) . . ?
C42 C37 C32 106.8(8) . . ?
C42 C37 H37 110.1 . . ?
O8 C39 C31 111.3(8) . . ?
O8 C39 H39 107.7 . . ?
O8 C39 C42 115.3(8) . . ?
C31 C39 H39 107.7 . . ?
C42 C39 C31 106.9(8) . . ?
C42 C39 H39 107.7 . . ?
C28 C40 H40A 109.5 . . ?
C28 C40 H40B 109.5 . . ?
C28 C40 H40C 109.5 . . ?
H40A C40 H40B 109.5 . . ?
H40A C40 H40C 109.5 . . ?
H40B C40 H40C 109.5 . . ?
O7 C41 C36 110.6(9) . . ?
O9 C41 O7 118.4(10) . . ?
O9 C41 C36 130.9(10) . . ?
O7 C42 C37 105.7(7) . . ?
O7 C42 C39 109.6(7) . . ?
O7 C42 H42 112.2 . . ?
C37 C42 H42 112.2 . . ?
C39 C42 C37 104.3(8) . . ?
C39 C42 H42 112.2 . . ?

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 C7 C8 O2 44.3(9) . . . . ?
O1 C7 C8 C9 159.0(7) . . . . ?
O2 C8 C9 C5 101.6(7) . . . . ?
O2 C8 C9 C10 -22.6(8) . . . . ?
O4 C25 C26 O6 41.9(10) . . . . ?
O4 C25 C26 C18 -83.4(8) . . . . ?
O8 C39 C42 O7 44.3(10) . . . . ?
O8 C39 C42 C37 157.1(7) . . . . ?
C1 C2 C3 C4 27.0(10) . . . . ?
C1 C6 C12 C11 -173.8(7) . . . . ?
C1E C15 C16 C17 162.1(7) . . . . ?
C1E C15 C20 C19 167.6(6) . . . . ?
C1E C15 C20 C21 -66.4(9) . . . . ?
C2 C1 C6 C5 -67.6(9) . . . . ?
C2 C1 C6 C12 60.0(9) . . . . ?
C2 C3 C4 C5 -61.9(9) . . . . ?
C2 C3 C4 C7 -179.5(7) . . . . ?
C3 C4 C5 C6 30.5(9) . . . . ?
C3 C4 C5 C9 -99.3(7) . . . . ?
C3 C4 C7 O1 -37.0(11) . . . . ?
C3 C4 C7 C8 84.9(9) . . . . ?
C4 C5 C6 C1 32.4(9) . . . . ?
C4 C5 C6 C12 -95.2(8) . . . . ?
C4 C5 C9 C8 -6.2(8) . . . . ?
C4 C5 C9 C10 108.1(8) . . . . ?
C4 C7 C8 O2 -80.8(8) . . . . ?
C4 C7 C8 C9 33.8(9) . . . . ?
C5 C4 C7 O1 -159.1(7) . . . . ?
C5 C4 C7 C8 -37.2(8) . . . . ?
C5 C6 C12 C11 -50.1(10) . . . . ?
C5 C9 C10 C11 31.0(10) . . . . ?
C5 C9 C10 C13 -92.5(8) . . . . ?
C6 C1 C2 C3 36.7(10) . . . . ?
C6 C5 C9 C8 -134.4(7) . . . . ?
C6 C5 C9 C10 -20.1(10) . . . . ?
C7 C4 C5 C6 155.9(7) . . . . ?
C7 C4 C5 C9 26.1(8) . . . . ?
C7 C8 C9 C5 -16.7(9) . . . . ?
C7 C8 C9 C10 -140.9(7) . . . . ?
C8 O2 C13 O3 -179.1(8) . . . . ?
C8 O2 C13 C10 2.9(10) . . . . ?
C8 C9 C10 C11 147.1(7) . . . . ?
C8 C9 C10 C13 23.5(9) . . . . ?
C9 C5 C6 C1 156.7(6) . . . . ?
C9 C5 C6 C12 29.1(10) . . . . ?
C9 C10 C11 C12 -50.7(10) . . . . ?
C9 C10 C13 O2 -17.4(10) . . . . ?
C9 C10 C13 O3 164.7(9) . . . . ?
C10 C11 C12 C6 60.5(9) . . . . ?
C11 C10 C13 O2 -143.0(8) . . . . ?
C11 C10 C13 O3 39.2(14) . . . . ?
C13 O2 C8 C7 127.2(7) . . . . ?
C13 O2 C8 C9 12.9(9) . . . . ?
C13 C10 C11 C12 68.2(10) . . . . ?
C14 C1 C2 C3 162.4(8) . . . . ?
C14 C1 C6 C5 168.2(7) . . . . ?
C14 C1 C6 C12 -64.1(9) . . . . ?
C15 C16 C17 C18 28.7(11) . . . . ?
C15 C20 C21 C22 -176.5(7) . . . . ?
C16 C15 C20 C19 -63.4(9) . . . . ?
C16 C15 C20 C21 62.6(9) . . . . ?
C16 C17 C18 C19 -60.4(10) . . . . ?
C16 C17 C18 C26 -179.5(7) . . . . ?
C17 C18 C19 C20 29.2(10) . . . . ?
C17 C18 C19 C24 -101.6(8) . . . . ?
C17 C18 C26 O6 -37.8(11) . . . . ?
C17 C18 C26 C25 90.4(9) . . . . ?
C18 C19 C20 C15 31.7(8) . . . . ?
C18 C19 C20 C21 -93.2(8) . . . . ?
C18 C19 C24 C23 108.9(8) . . . . ?
C18 C19 C24 C25 -5.6(8) . . . . ?
C19 C18 C26 O6 -162.4(7) . . . . ?
C19 C18 C26 C25 -34.2(8) . . . . ?
C19 C20 C21 C22 -53.3(9) . . . . ?
C19 C24 C25 O4 102.6(7) . . . . ?
C19 C24 C25 C26 -15.5(8) . . . . ?
C20 C15 C16 C17 31.9(10) . . . . ?
C20 C19 C24 C23 -19.2(10) . . . . ?
C20 C19 C24 C25 -133.7(7) . . . . ?
C20 C21 C22 C23 61.9(8) . . . . ?
C21 C22 C23 C24 -49.6(10) . . . . ?
C21 C22 C23 C27 71.4(9) . . . . ?
C22 C23 C24 C19 28.5(11) . . . . ?
C22 C23 C24 C25 144.6(7) . . . . ?
C22 C23 C27 O4 -139.3(7) . . . . ?
C22 C23 C27 O5 38.5(13) . . . . ?
C23 C24 C25 O4 -21.0(9) . . . . ?
C23 C24 C25 C26 -139.1(7) . . . . ?
C24 C19 C20 C15 156.5(7) . . . . ?
C24 C19 C20 C21 31.6(10) . . . . ?
C24 C23 C27 O4 -11.8(9) . . . . ?
C24 C23 C27 O5 166.1(8) . . . . ?
C24 C25 C26 O6 156.7(7) . . . . ?
C24 C25 C26 C18 31.3(8) . . . . ?
C25 O4 C27 O5 180.0(8) . . . . ?
C25 O4 C27 C23 -2.0(10) . . . . ?
C26 C18 C19 C20 154.8(6) . . . . ?
C26 C18 C19 C24 24.0(8) . . . . ?
C27 O4 C25 C24 14.8(9) . . . . ?
C27 O4 C25 C26 129.8(8) . . . . ?
C27 C23 C24 C19 -96.6(8) . . . . ?
C27 C23 C24 C25 19.5(8) . . . . ?
C28 C29 C30 C31 28.8(11) . . . . ?
C28 C33 C34 C35 -175.9(7) . . . . ?
C29 C28 C33 C32 -63.8(9) . . . . ?
C29 C28 C33 C34 62.5(10) . . . . ?
C29 C30 C31 C32 -60.5(10) . . . . ?
C29 C30 C31 C39 -179.4(8) . . . . ?
C30 C31 C32 C33 28.3(10) . . . . ?
C30 C31 C32 C37 -101.8(8) . . . . ?
C30 C31 C39 O8 -39.1(11) . . . . ?
C30 C31 C39 C42 87.7(9) . . . . ?
C31 C32 C33 C28 31.5(9) . . . . ?
C31 C32 C33 C34 -94.3(9) . . . . ?
C31 C32 C37 C36 107.8(8) . . . . ?
C31 C32 C37 C42 -6.1(9) . . . . ?
C31 C39 C42 O7 -80.0(8) . . . . ?
C31 C39 C42 C37 32.8(10) . . . . ?
C32 C31 C39 O8 -163.0(7) . . . . ?
C32 C31 C39 C42 -36.3(9) . . . . ?
C32 C33 C34 C35 -52.5(9) . . . . ?
C32 C37 C42 O7 99.7(8) . . . . ?
C32 C37 C42 C39 -15.8(9) . . . . ?
C33 C28 C29 C30 32.8(11) . . . . ?
C33 C32 C37 C36 -20.3(11) . . . . ?
C33 C32 C37 C42 -134.2(7) . . . . ?
C33 C34 C35 C36 64.1(10) . . . . ?
C34 C35 C36 C37 -53.4(11) . . . . ?
C34 C35 C36 C41 68.4(11) . . . . ?
C35 C36 C37 C32 32.0(11) . . . . ?
C35 C36 C37 C42 148.3(8) . . . . ?
C35 C36 C41 O7 -139.9(8) . . . . ?
C35 C36 C41 O9 36.9(16) . . . . ?
C36 C37 C42 O7 -23.6(9) . . . . ?
C36 C37 C42 C39 -139.2(8) . . . . ?
C37 C32 C33 C28 156.1(7) . . . . ?
C37 C32 C33 C34 30.2(10) . . . . ?
C37 C36 C41 O7 -12.9(10) . . . . ?
C37 C36 C41 O9 164.0(11) . . . . ?
C39 C31 C32 C33 155.5(7) . . . . ?
C39 C31 C32 C37 25.4(8) . . . . ?
C40 C28 C29 C30 161.3(8) . . . . ?
C40 C28 C33 C32 167.5(8) . . . . ?
C40 C28 C33 C34 -66.1(10) . . . . ?
C41 O7 C42 C37 17.1(10) . . . . ?
C41 O7 C42 C39 129.0(8) . . . . ?
C41 C36 C37 C32 -94.4(9) . . . . ?
C41 C36 C37 C42 22.0(9) . . . . ?
C42 O7 C41 O9 -180.0(9) . . . . ?
C42 O7 C41 C36 -2.7(10) . . . . ?

