# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2018

####################################################################### 
# 
# 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_160307_s3_xwy
_database_code_depnum_ccdc_archive 'CCDC 1820653'
_audit_update_record             
;
2018-01-30 deposited with the CCDC.
2018-03-15 downloaded from the CCDC.
;
_audit_creation_date             2016-03-08
_audit_creation_method           
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C23 H32 O6'
_chemical_formula_sum            'C23 H32 O6'
_chemical_formula_weight         404.49
_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'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, -y, -z'

_cell_length_a                   8.2403(4)
_cell_length_b                   11.2635(5)
_cell_length_c                   11.6154(7)
_cell_angle_alpha                80.692(4)
_cell_angle_beta                 75.701(5)
_cell_angle_gamma                83.849(4)
_cell_volume                     1028.38(9)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    2467
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      28.8470
_cell_measurement_theta_min      3.6580
_exptl_absorpt_coefficient_mu    0.093
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.90426
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.306
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             436
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.25
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0184
_diffrn_reflns_av_unetI/netI     0.0375
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            8586
_diffrn_reflns_theta_full        26.37
_diffrn_reflns_theta_max         26.37
_diffrn_reflns_theta_min         3.04
_diffrn_ambient_temperature      293.15
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0874
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -25.00   20.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      -14.9669  -99.0000 -120.0000 45

#__ type_ start__ end____ width___ exp.time_
  2 omega  -86.00  -51.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      -14.9669 -178.0000  120.0000 35

#__ type_ start__ end____ width___ exp.time_
  3 omega  -18.00    7.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      -14.9669  -99.0000  150.0000 25

#__ type_ start__ end____ width___ exp.time_
  4 omega  -23.00   22.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      -14.9669  -99.0000  -30.0000 45

#__ type_ start__ end____ width___ exp.time_
  5 omega  -25.00   30.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       16.6856  -99.0000  -30.0000 55

#__ type_ start__ end____ width___ exp.time_
  6 omega   -1.00   86.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       16.6856   38.0000  150.0000 87

#__ type_ start__ end____ width___ exp.time_
  7 omega  -54.00   41.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       16.6856  -19.0000  -30.0000 95
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0002646000
_diffrn_orient_matrix_UB_12      -0.0248187000
_diffrn_orient_matrix_UB_13      0.0601090000
_diffrn_orient_matrix_UB_21      0.0853414000
_diffrn_orient_matrix_UB_22      -0.0210257000
_diffrn_orient_matrix_UB_23      -0.0185931000
_diffrn_orient_matrix_UB_31      0.0254267000
_diffrn_orient_matrix_UB_32      0.0550845000
_diffrn_orient_matrix_UB_33      0.0096066000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                3024
_reflns_number_total             4204
_reflns_odcompleteness_completeness 99.86
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.252
_refine_diff_density_min         -0.154
_refine_diff_density_rms         0.034
_refine_ls_extinction_coef       0.0046(17)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     275
_refine_ls_number_reflns         4204
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0702
_refine_ls_R_factor_gt           0.0474
_refine_ls_restrained_S_all      1.029
_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)+(0.0477P)²+0.1824P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1041
_refine_ls_wR_factor_ref         0.1173
_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 C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C6(H6), C8(H8), C9(H9), C10(H10), C12(H12), C14(H14), C16(H16), C17(H17)
2.b Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C3(H3A,H3B), C4(H4A,H4B), C7(H7A,H7B), C13(H13A,H13B)
2.c Idealised Me refined as rotating group:
 C20(H20A,H20B,H20C), C21(H21A,H21B,H21C), C22(H22A,H22B,H22C), C23(H23A,H23B,
 H23C)
;
_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_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_refinement_flags_posn
C1 C 0.5406(3) 0.74098(17) 0.21188(18) 0.0501(5) Uani 1 d . . .
C2 C 0.6734(3) 0.7742(2) 0.1015(2) 0.0635(6) Uani 1 d . . .
H2A H 0.6758 0.8613 0.0836 0.076 Uiso 1 calc . . R
H2B H 0.6497 0.7446 0.0339 0.076 Uiso 1 calc . . R
C3 C 0.8429(3) 0.7185(2) 0.1222(2) 0.0671(6) Uani 1 d . . .
H3A H 0.8411 0.6313 0.1376 0.080 Uiso 1 calc . . R
H3B H 0.9305 0.7394 0.0509 0.080 Uiso 1 calc . . R
C4 C 0.8797(3) 0.7637(2) 0.22695(18) 0.0571(5) Uani 1 d . . .
H4A H 0.8967 0.8491 0.2053 0.068 Uiso 1 calc . . R
H4B H 0.9842 0.7232 0.2413 0.068 Uiso 1 calc . . R
C5 C 0.7441(2) 0.74628(16) 0.34472(16) 0.0413(4) Uani 1 d . . .
C6 C 0.7888(2) 0.82251(15) 0.43081(16) 0.0398(4) Uani 1 d . . .
H6 H 0.8213 0.8992 0.3814 0.048 Uiso 1 calc . . R
C7 C 0.9444(2) 0.77102(17) 0.48147(17) 0.0449(5) Uani 1 d . . .
H7A H 0.9680 0.6859 0.4744 0.054 Uiso 1 calc . . R
H7B H 1.0427 0.8134 0.4381 0.054 Uiso 1 calc . . R
C8 C 0.8984(2) 0.79023(15) 0.61408(16) 0.0409(4) Uani 1 d . . .
H8 H 0.9970 0.8102 0.6381 0.049 Uiso 1 calc . . R
C9 C 0.8214(2) 0.67951(15) 0.69622(16) 0.0377(4) Uani 1 d . . .
H9 H 0.8733 0.6082 0.6592 0.045 Uiso 1 calc . . R
C10 C 0.6294(2) 0.67718(14) 0.71548(15) 0.0349(4) Uani 1 d . . .
H10 H 0.6020 0.5936 0.7209 0.042 Uiso 1 calc . . R
C11 C 0.5513(2) 0.75622(14) 0.61783(15) 0.0345(4) Uani 1 d . . .
C12 C 0.4936(2) 0.67870(16) 0.54121(17) 0.0410(4) Uani 1 d . . .
H12 H 0.3999 0.6353 0.5940 0.049 Uiso 1 calc . . R
C13 C 0.4281(3) 0.7482(2) 0.43720(18) 0.0567(5) Uani 1 d . . .
H13A H 0.3637 0.8204 0.4630 0.068 Uiso 1 calc . . R
H13B H 0.3520 0.6992 0.4170 0.068 Uiso 1 calc . . R
C14 C 0.5637(2) 0.78522(16) 0.32355(16) 0.0438(4) Uani 1 d . . .
H14 H 0.5548 0.8736 0.3083 0.053 Uiso 1 calc . . R
C15 C 0.7450(2) 0.61530(16) 0.40058(17) 0.0439(4) Uani 1 d . . .
C16 C 0.7726(2) 0.90032(15) 0.60912(17) 0.0426(4) Uani 1 d . . .
H16 H 0.8322 0.9672 0.5571 0.051 Uiso 1 calc . . R
C17 C 0.6568(2) 0.85754(14) 0.54166(16) 0.0377(4) Uani 1 d . . .
H17 H 0.5826 0.9257 0.5169 0.045 Uiso 1 calc . . R
C18 C 0.3806(2) 0.76452(16) 0.81096(17) 0.0455(5) Uani 1 d . . .
C19 C 0.4189(4) 0.6750(3) 0.2084(3) 0.0784(8) Uani 1 d . . .
H19A H 0.425(3) 0.650(2) 0.130(2) 0.087(8) Uiso 1 d . . .
H19B H 0.328(4) 0.647(2) 0.280(3) 0.098(9) Uiso 1 d . . .
C20 C 0.8384(3) 0.55732(17) 0.87881(18) 0.0544(5) Uani 1 d . . .
H20A H 0.8907 0.5502 0.9451 0.082 Uiso 1 calc . . GR
H20B H 0.8850 0.4943 0.8312 0.082 Uiso 1 calc . . GR
H20C H 0.7198 0.5506 0.9085 0.082 Uiso 1 calc . . GR
C21 C 0.7874(3) 0.9749(2) 0.7851(2) 0.0683(7) Uani 1 d . . .
H21A H 0.7192 1.0137 0.8501 0.102 Uiso 1 calc . . GR
H21B H 0.8667 1.0293 0.7353 0.102 Uiso 1 calc . . GR
H21C H 0.8464 0.9039 0.8167 0.102 Uiso 1 calc . . GR
C22 C 0.3187(3) 0.8660(2) 0.8846(2) 0.0689(7) Uani 1 d . . .
H22A H 0.3976 0.9273 0.8611 0.103 Uiso 1 calc . . GR
H22B H 0.3076 0.8355 0.9681 0.103 Uiso 1 calc . . GR
H22C H 0.2116 0.8997 0.8716 0.103 Uiso 1 calc . . GR
C23 C 0.2634(3) 0.66274(19) 0.8452(2) 0.0599(6) Uani 1 d . . .
H23A H 0.2465 0.6347 0.9295 0.090 Uiso 1 calc . . GR
H23B H 0.3120 0.5976 0.8008 0.090 Uiso 1 calc . . GR
H23C H 0.1574 0.6915 0.8268 0.090 Uiso 1 calc . . GR
O1 O 0.62585(16) 0.58733(10) 0.50124(12) 0.0460(3) Uani 1 d . . .
O2 O 0.54399(15) 0.72202(11) 0.82368(11) 0.0421(3) Uani 1 d . . .
O3 O 0.40157(15) 0.81229(10) 0.68632(11) 0.0434(3) Uani 1 d . . .
O4 O 0.68385(18) 0.94235(11) 0.71620(13) 0.0544(4) Uani 1 d . . .
O5 O 0.84430(19) 0.53568(12) 0.36448(14) 0.0645(4) Uani 1 d . . .
O6 O 0.86778(16) 0.67096(11) 0.80730(11) 0.0456(3) Uani 1 d . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.491(3) . ?
C1 C14 1.523(3) . ?
C1 C19 1.322(3) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C2 C3 1.526(3) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C3 C4 1.500(3) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C4 C5 1.537(3) . ?
C5 C6 1.549(2) . ?
C5 C14 1.571(2) . ?
C5 C15 1.513(3) . ?
C6 H6 0.9800 . ?
C6 C7 1.559(2) . ?
C6 C17 1.542(2) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C7 C8 1.538(3) . ?
C8 H8 0.9800 . ?
C8 C9 1.534(2) . ?
C8 C16 1.532(2) . ?
C9 H9 0.9800 . ?
C9 C10 1.545(2) . ?
C9 O6 1.420(2) . ?
C10 H10 0.9800 . ?
C10 C11 1.550(2) . ?
C10 O2 1.422(2) . ?
C11 C12 1.527(2) . ?
C11 C17 1.532(2) . ?
C11 O3 1.4371(19) . ?
C12 H12 0.9800 . ?
C12 C13 1.513(3) . ?
C12 O1 1.459(2) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C13 C14 1.536(3) . ?
C14 H14 0.9800 . ?
C15 O1 1.345(2) . ?
C15 O5 1.202(2) . ?
C16 H16 0.9800 . ?
C16 C17 1.531(2) . ?
C16 O4 1.405(2) . ?
C17 H17 0.9800 . ?
C18 C22 1.508(3) . ?
C18 C23 1.518(3) . ?
C18 O2 1.415(2) . ?
C18 O3 1.435(2) . ?
C19 H19A 0.99(3) . ?
C19 H19B 1.01(3) . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
C20 O6 1.418(2) . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?
C21 O4 1.415(2) . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?
C23 H23A 0.9600 . ?
C23 H23B 0.9600 . ?
C23 H23C 0.9600 . ?

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
C2 C1 C14 114.38(18) . . ?
C19 C1 C2 120.3(2) . . ?
C19 C1 C14 125.3(2) . . ?
C1 C2 H2A 109.9 . . ?
C1 C2 H2B 109.9 . . ?
C1 C2 C3 108.84(18) . . ?
H2A C2 H2B 108.3 . . ?
C3 C2 H2A 109.9 . . ?
C3 C2 H2B 109.9 . . ?
C2 C3 H3A 109.6 . . ?
C2 C3 H3B 109.6 . . ?
H3A C3 H3B 108.2 . . ?
C4 C3 C2 110.06(18) . . ?
C4 C3 H3A 109.6 . . ?
C4 C3 H3B 109.6 . . ?
C3 C4 H4A 108.4 . . ?
C3 C4 H4B 108.4 . . ?
C3 C4 C5 115.68(19) . . ?
H4A C4 H4B 107.4 . . ?
C5 C4 H4A 108.4 . . ?
C5 C4 H4B 108.4 . . ?
C4 C5 C6 106.68(15) . . ?
C4 C5 C14 111.56(15) . . ?
C6 C5 C14 111.42(14) . . ?
C15 C5 C4 110.72(16) . . ?
C15 C5 C6 108.94(14) . . ?
C15 C5 C14 107.53(15) . . ?
C5 C6 H6 105.2 . . ?
C5 C6 C7 114.89(14) . . ?
C7 C6 H6 105.2 . . ?
C17 C6 C5 121.06(14) . . ?
C17 C6 H6 105.2 . . ?
C17 C6 C7 103.90(14) . . ?
C6 C7 H7A 110.6 . . ?
C6 C7 H7B 110.6 . . ?
H7A C7 H7B 108.7 . . ?
C8 C7 C6 105.88(14) . . ?
C8 C7 H7A 110.6 . . ?
C8 C7 H7B 110.6 . . ?
C7 C8 H8 110.5 . . ?
C9 C8 C7 111.61(14) . . ?
C9 C8 H8 110.5 . . ?
C16 C8 C7 100.19(14) . . ?
C16 C8 H8 110.5 . . ?
C16 C8 C9 113.11(15) . . ?
C8 C9 H9 107.4 . . ?
C8 C9 C10 115.11(14) . . ?
C10 C9 H9 107.4 . . ?
O6 C9 C8 108.11(14) . . ?
O6 C9 H9 107.4 . . ?
O6 C9 C10 111.12(14) . . ?
C9 C10 H10 108.7 . . ?
C9 C10 C11 115.63(14) . . ?
C11 C10 H10 108.7 . . ?
O2 C10 C9 110.82(13) . . ?
O2 C10 H10 108.7 . . ?
O2 C10 C11 104.16(12) . . ?
C12 C11 C10 111.30(13) . . ?
C12 C11 C17 112.34(14) . . ?
C17 C11 C10 115.56(14) . . ?
O3 C11 C10 103.25(13) . . ?
O3 C11 C12 106.25(13) . . ?
O3 C11 C17 107.21(12) . . ?
C11 C12 H12 106.5 . . ?
C13 C12 C11 115.05(15) . . ?
C13 C12 H12 106.5 . . ?
O1 C12 C11 110.28(14) . . ?
O1 C12 H12 106.5 . . ?
O1 C12 C13 111.34(15) . . ?
C12 C13 H13A 108.5 . . ?
C12 C13 H13B 108.5 . . ?
C12 C13 C14 114.99(16) . . ?
H13A C13 H13B 107.5 . . ?
C14 C13 H13A 108.5 . . ?
C14 C13 H13B 108.5 . . ?
C1 C14 C5 111.30(15) . . ?
C1 C14 C13 113.87(17) . . ?
C1 C14 H14 106.8 . . ?
C5 C14 H14 106.8 . . ?
C13 C14 C5 110.91(15) . . ?
C13 C14 H14 106.8 . . ?
O1 C15 C5 116.38(15) . . ?
O5 C15 C5 125.78(19) . . ?
O5 C15 O1 117.82(17) . . ?
C8 C16 H16 107.9 . . ?
C17 C16 C8 100.42(13) . . ?
C17 C16 H16 107.9 . . ?
O4 C16 C8 119.54(15) . . ?
O4 C16 H16 107.9 . . ?
O4 C16 C17 112.53(15) . . ?
C6 C17 H17 109.6 . . ?
C11 C17 C6 116.00(13) . . ?
C11 C17 H17 109.6 . . ?
C16 C17 C6 99.49(14) . . ?
C16 C17 C11 112.10(14) . . ?
C16 C17 H17 109.6 . . ?
C22 C18 C23 112.41(18) . . ?
O2 C18 C22 108.84(17) . . ?
O2 C18 C23 111.01(15) . . ?
O2 C18 O3 104.83(14) . . ?
O3 C18 C22 108.73(16) . . ?
O3 C18 C23 110.72(17) . . ?
C1 C19 H19A 115.3(16) . . ?
C1 C19 H19B 124.0(16) . . ?
H19A C19 H19B 121(2) . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
O6 C20 H20A 109.5 . . ?
O6 C20 H20B 109.5 . . ?
O6 C20 H20C 109.5 . . ?
H21A C21 H21B 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
O4 C21 H21A 109.5 . . ?
O4 C21 H21B 109.5 . . ?
O4 C21 H21C 109.5 . . ?
C18 C22 H22A 109.5 . . ?
C18 C22 H22B 109.5 . . ?
C18 C22 H22C 109.5 . . ?
H22A C22 H22B 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C18 C23 H23A 109.5 . . ?
C18 C23 H23B 109.5 . . ?
C18 C23 H23C 109.5 . . ?
H23A C23 H23B 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C15 O1 C12 119.32(14) . . ?
C18 O2 C10 106.99(13) . . ?
C18 O3 C11 109.50(12) . . ?
C16 O4 C21 114.13(17) . . ?
C20 O6 C9 112.61(14) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_111031_s2_ch
_database_code_depnum_ccdc_archive 'CCDC 1820658'
_audit_update_record             
;
2018-01-30 deposited with the CCDC.
2018-03-15 downloaded from the CCDC.
;
_audit_creation_date             2011-11-02
_audit_creation_method           
;
  Olex2 1.1
  (compiled 2011.09.07 svn.r1971, GUI svn.r3853)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C13 H20 O4'
_chemical_formula_sum            'C13 H20 O4'
_chemical_formula_weight         240.29
_chemical_melting_point          ?
_chemical_oxdiff_formula         C20H20O5
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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, y+1/2, -z+1/2'
3 '-x, -y, -z'
4 'x, -y-1/2, z-1/2'

_cell_length_a                   10.8545(6)
_cell_length_b                   11.1988(4)
_cell_length_c                   10.9655(6)
_cell_angle_alpha                90.00
_cell_angle_beta                 117.846(7)
_cell_angle_gamma                90.00
_cell_volume                     1178.60(9)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1668
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      29.1913
_cell_measurement_theta_min      3.6107
_exptl_absorpt_coefficient_mu    0.099
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.93181
_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            colorless
_exptl_crystal_density_diffrn    1.354
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             520
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.12
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0158
_diffrn_reflns_av_unetI/netI     0.0257
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            4710
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         3.64
_diffrn_ambient_temperature      293.15
_diffrn_detector_area_resol_mean 16.0874
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega   -1.00   88.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       19.8611   38.0000    0.0000 89

#__ type_ start__ end____ width___ exp.time_
  2 omega   11.00   38.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       19.8611   38.0000 -180.0000 27

#__ type_ start__ end____ width___ exp.time_
  3 omega  -52.00   43.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       19.8611  -38.0000 -180.0000 95

#__ type_ start__ end____ width___ exp.time_
  4 omega  -50.00  -25.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       19.8611  -77.0000   30.0000 25
;
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0604413000
_diffrn_orient_matrix_UB_12      0.0319177000
_diffrn_orient_matrix_UB_13      0.0099159000
_diffrn_orient_matrix_UB_21      0.0421589000
_diffrn_orient_matrix_UB_22      -0.0406411000
_diffrn_orient_matrix_UB_23      0.0526259000
_diffrn_orient_matrix_UB_31      0.0058635000
_diffrn_orient_matrix_UB_32      -0.0366012000
_diffrn_orient_matrix_UB_33      -0.0498280000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_source_current           n/a
_diffrn_source_voltage           n/a
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                1680
_reflns_number_total             2068
_reflns_odcompleteness_completeness 99.73
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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, G.M. Sheldrick, Acta Cryst.
2008). A64, 112-122
;
_computing_structure_solution    
;
SHELXS, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_refine_diff_density_max         0.201
_refine_diff_density_min         -0.165
_refine_diff_density_rms         0.035
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     163
_refine_ls_number_reflns         2068
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0516
_refine_ls_R_factor_gt           0.0402
_refine_ls_restrained_S_all      1.025
_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)+(0.0432P)²+0.3590P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0916
_refine_ls_wR_factor_ref         0.1002
_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 -1.25115(13) -0.16308(10) -0.64875(12) 0.0404(3) Uani 1 1 d . . .
O2 O -1.25091(16) 0.15559(12) -1.05449(13) 0.0530(4) Uani 1 1 d . . .
H2 H -1.178(3) 0.201(2) -1.018(3) 0.079(8) Uiso 1 1 d . . .
O3 O -0.98416(14) -0.19409(11) -0.57188(12) 0.0421(3) Uani 1 1 d . . .
H3 H -1.062(3) -0.211(2) -0.574(3) 0.081(9) Uiso 1 1 d . . .
O4 O -1.20870(13) -0.35856(10) -0.79147(13) 0.0456(3) Uani 1 1 d . . .
C5 C -1.3067(2) 0.19086(15) -0.86544(19) 0.0445(5) Uani 1 1 d . . .
H5A H -1.3524 0.2583 -0.9249 0.053 Uiso 1 1 calc R . .
H5B H -1.2234 0.2201 -0.7868 0.053 Uiso 1 1 calc R . .
C6 C -1.4038(2) 0.13732(16) -0.8152(2) 0.0485(5) Uani 1 1 d . . .
H6A H -1.4834 0.1032 -0.8939 0.058 Uiso 1 1 calc R . .
H6B H -1.4381 0.2014 -0.7798 0.058 Uiso 1 1 calc R . .
C7 C -1.3408(2) 0.04152(17) -0.7043(2) 0.0462(5) Uani 1 1 d . . .
H7A H -1.2827 0.0810 -0.6173 0.055 Uiso 1 1 calc R . .
H7B H -1.4163 0.0031 -0.6954 0.055 Uiso 1 1 calc R . .
C8 C -1.25509(17) -0.05452(14) -0.72475(16) 0.0328(4) Uani 1 1 d . . .
C9 C -1.11634(17) -0.01742(14) -0.71478(16) 0.0318(4) Uani 1 1 d . . .
H9 H -1.0699 0.0421 -0.6419 0.038 Uiso 1 1 calc R . .
C10 C -1.13448(17) 0.02914(14) -0.85533(16) 0.0331(4) Uani 1 1 d . . .
H10 H -1.0540 0.0798 -0.8367 0.040 Uiso 1 1 calc R . .
C11 C -1.26529(18) 0.10137(15) -0.94385(17) 0.0380(4) Uani 1 1 d . . .
H11 H -1.3421 0.0440 -0.9858 0.046 Uiso 1 1 calc R . .
C12 C -1.1227(2) -0.08464(15) -0.93017(18) 0.0411(4) Uani 1 1 d . . .
H12A H -1.2072 -0.0961 -1.0163 0.049 Uiso 1 1 calc R . .
H12B H -1.0447 -0.0778 -0.9499 0.049 Uiso 1 1 calc R . .
C13 C -1.10057(17) -0.18946(14) -0.83227(16) 0.0328(4) Uani 1 1 d . . .
H13 H -1.0417 -0.2507 -0.8427 0.039 Uiso 1 1 calc R . .
C14 C -1.02186(17) -0.12540(14) -0.69351(16) 0.0334(4) Uani 1 1 d . . .
H14 H -0.9352 -0.0949 -0.6889 0.040 Uiso 1 1 calc R . .
C15 C -1.31609(18) -0.16715(14) -0.79763(16) 0.0351(4) Uani 1 1 d . . .
H15 H -1.4180 -0.1718 -0.8463 0.042 Uiso 1 1 calc R . .
C16 C -1.23855(17) -0.24301(14) -0.85429(16) 0.0336(4) Uani 1 1 d . . .
H16 H -1.2984 -0.2532 -0.9536 0.040 Uiso 1 1 calc R . .
C17 C -1.3254(2) -0.43236(19) -0.8335(2) 0.0624(6) Uani 1 1 d . . .
H17A H -1.3692 -0.4420 -0.9319 0.094 Uiso 1 1 calc R . .
H17B H -1.3903 -0.3967 -0.8076 0.094 Uiso 1 1 calc R . .
H17C H -1.2971 -0.5090 -0.7900 0.094 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 C8 1.4633(19) . ?
O1 C15 1.445(2) . ?
O2 C11 1.429(2) . ?
O3 C14 1.4242(19) . ?
O4 C16 1.4302(19) . ?
O4 C17 1.398(2) . ?
C5 C6 1.522(3) . ?
C5 C11 1.519(2) . ?
C6 C7 1.524(3) . ?
C7 C8 1.506(2) . ?
C8 C9 1.516(2) . ?
C8 C15 1.474(2) . ?
C9 C10 1.550(2) . ?
C9 C14 1.531(2) . ?
C10 C11 1.525(2) . ?
C10 C12 1.553(2) . ?
C12 C13 1.532(2) . ?
C13 C14 1.531(2) . ?
C13 C16 1.524(2) . ?
C15 C16 1.518(2) . ?

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
C15 O1 C8 60.91(10) . . ?
C17 O4 C16 114.16(14) . . ?
C11 C5 C6 112.51(15) . . ?
C5 C6 C7 116.00(16) . . ?
C8 C7 C6 117.47(15) . . ?
O1 C8 C7 111.34(13) . . ?
O1 C8 C9 115.01(13) . . ?
O1 C8 C15 58.95(10) . . ?
C7 C8 C9 117.11(15) . . ?
C15 C8 C7 122.64(15) . . ?
C15 C8 C9 116.93(14) . . ?
C8 C9 C10 111.10(13) . . ?
C8 C9 C14 111.51(13) . . ?
C14 C9 C10 100.49(12) . . ?
C9 C10 C12 104.23(12) . . ?
C11 C10 C9 117.35(14) . . ?
C11 C10 C12 112.39(14) . . ?
O2 C11 C5 112.26(14) . . ?
O2 C11 C10 109.11(14) . . ?
C5 C11 C10 115.06(14) . . ?
C13 C12 C10 106.45(13) . . ?
C14 C13 C12 99.75(13) . . ?
C16 C13 C12 111.69(14) . . ?
C16 C13 C14 113.12(13) . . ?
O3 C14 C9 116.63(13) . . ?
O3 C14 C13 117.41(13) . . ?
C9 C14 C13 101.27(13) . . ?
O1 C15 C8 60.14(10) . . ?
O1 C15 C16 114.13(13) . . ?
C8 C15 C16 120.41(14) . . ?
O4 C16 C13 107.15(13) . . ?
O4 C16 C15 110.70(13) . . ?
C15 C16 C13 113.99(13) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O2 H2 O3 0.86(3) 1.96(3) 2.822(2) 177(2) 2_353
O3 H3 O1 0.86(3) 1.90(3) 2.6358(18) 143(2) .

