# Electronic Supplementary Material (ESI) for Chemical Science.
# 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_424cf1
_database_code_depnum_ccdc_archive 'CCDC 1525188'
_audit_update_record             
;
2017-01-02 deposited with the CCDC.
2017-01-30 downloaded from the CCDC.
;

_audit_creation_date             2014-06-10T12:47:24-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_name_systematic        
;
 (2S,3R,3aR,7aS)-5-Oxo-2-phenylhexahydro-4H-furo[2,3-b]pyran-3-carbaldehyde
;
_chemical_formula_moiety         'C14 H14 O4'
_chemical_formula_sum            'C14 H14 O4'
_chemical_formula_weight         246.25
_chemical_compound_source        'synthesis as described'
_chemical_absolute_configuration 2S,3R,3aR,7aS

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 1 21 1'
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_Int_Tables_number      4
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   9.16074(6)
_cell_length_b                   6.01447(4)
_cell_length_c                   10.6243(1)
_cell_angle_alpha                90
_cell_angle_beta                 92.0730(10)
_cell_angle_gamma                90
_cell_volume                     584.984(8)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    18931
_cell_measurement_theta_min      4.142
_cell_measurement_theta_max      74.045
_cell_measurement_wavelength     1.54184

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.234
_exptl_crystal_size_mid          0.1168
_exptl_crystal_size_min          0.0601
_exptl_crystal_density_diffrn    1.398
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             260
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 -4 1 0.115
-1 0 7 0.0543
0 3 4 0.0698
1 0 -7 0.0441
6 0 -1 0.0187
-6 0 0 0.0331
-1 -2 5 0.0823
1 -2 -6 0.0796

_exptl_special_details           
;
 ?
;

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    0.849
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   
;
        CrysAlisPro, Agilent Technologies,
        Version 1.171.36.24 (release 03-12-2012 CrysAlis171 .NET)
        (compiled Dec  3 2012,18:21:49)
Analytical numeric absorption correction using a multifaceted crystal
                        model based on expressions derived by R.C. Clark & J.S.
        (Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
;
_exptl_absorpt_correction_T_min  0.882
_exptl_absorpt_correction_T_max  0.958

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'Nova (Cu) X-ray micro-source'
_diffrn_radiation_monochromator  'Multilayer optics'
_diffrn_source_voltage           50
_diffrn_source_current           0.8
_diffrn_source_power             0.04
_diffrn_radiation_probe          x-ray
_diffrn_measurement_device_type  'Agilent SuperNova'
_diffrn_measurement_method       'ω scans'
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            Atlas
_diffrn_measurement_device       'κ-geometry diffractometer'
_diffrn_detector_area_resol_mean 5.2012
_diffrn_orient_matrix_ub_11      -0.13996
_diffrn_orient_matrix_ub_12      0.1397636
_diffrn_orient_matrix_ub_13      0.0103515
_diffrn_orient_matrix_ub_21      -0.0898937
_diffrn_orient_matrix_ub_22      -0.1888079
_diffrn_orient_matrix_ub_23      -0.0627991
_diffrn_orient_matrix_ub_31      -0.0254241
_diffrn_orient_matrix_ub_32      -0.1021553
_diffrn_orient_matrix_ub_33      0.1303888
_diffrn_reflns_av_R_equivalents  0.0556
_diffrn_reflns_av_unetI/netI     0.0187
_diffrn_reflns_number            21603
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         4.16
_diffrn_reflns_theta_max         71.98
_diffrn_reflns_theta_full        71.98
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_reflns_number_total             2281
_reflns_number_gt                2269
_reflns_threshold_expression     >2σ(I)
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega   10.00   43.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.5756    0.0000  120.0000 33

#__ type_ start__ end____ width___ exp.time_
  2 omega -128.00    8.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.5756    0.0000  120.0000 136

#__ type_ start__ end____ width___ exp.time_
  3 omega -115.00  -15.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.5756  -38.0000  -60.0000 100

#__ type_ start__ end____ width___ exp.time_
  4 omega  -73.00  -39.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -83.0000  125.0000 -120.0000 34

#__ type_ start__ end____ width___ exp.time_
  5 omega  -39.00   -9.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -83.0000   45.0000  -30.0000 30

#__ type_ start__ end____ width___ exp.time_
  6 omega  -75.00  -43.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -83.0000   45.0000  -30.0000 32

#__ type_ start__ end____ width___ exp.time_
  7 omega  107.00  133.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.3609   30.0000  -60.0000 26

#__ type_ start__ end____ width___ exp.time_
  8 omega   45.00   89.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.3609  -94.0000  -90.0000 44

#__ type_ start__ end____ width___ exp.time_
  9 omega   89.00  157.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.3609   45.0000  120.0000 68

#__ type_ start__ end____ width___ exp.time_
 10 omega   83.00  155.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.3609   77.0000   60.0000 72

#__ type_ start__ end____ width___ exp.time_
 11 omega   36.00   72.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.3609  -45.0000  -90.0000 36

#__ type_ start__ end____ width___ exp.time_
 12 omega   96.00  156.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.3609   45.0000 -150.0000 60

#__ type_ start__ end____ width___ exp.time_
 13 omega   49.00   77.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.3609  -45.0000    0.0000 28

#__ type_ start__ end____ width___ exp.time_
 14 omega   30.00   64.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.3609  -30.0000   60.0000 34

#__ type_ start__ end____ width___ exp.time_
 15 omega   44.00   93.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.3609  -94.0000   30.0000 49

#__ type_ start__ end____ width___ exp.time_
 16 omega   35.00  122.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.3609 -125.0000 -120.0000 87

#__ type_ start__ end____ width___ exp.time_
 17 omega   39.00   76.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.3609  -45.0000 -180.0000 37

#__ type_ start__ end____ width___ exp.time_
 18 omega   41.00   67.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.3609  -94.0000  -60.0000 26

#__ type_ start__ end____ width___ exp.time_
 19 omega   71.00  103.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.3609  -94.0000  -60.0000 32

#__ type_ start__ end____ width___ exp.time_
 20 omega   31.00   62.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.3609  -30.0000  -60.0000 31

#__ type_ start__ end____ width___ exp.time_
 21 omega   35.00   62.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.3609  -30.0000  -30.0000 27

#__ type_ start__ end____ width___ exp.time_
 22 omega   89.00  155.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.3609   77.0000  -60.0000 66

#__ type_ start__ end____ width___ exp.time_
 23 omega   35.00   60.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.3609  -45.0000  -60.0000 25

#__ type_ start__ end____ width___ exp.time_
 24 omega  -94.00   -2.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.5756  125.0000   60.0000 92

#__ type_ start__ end____ width___ exp.time_
 25 omega  -40.00  -15.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -83.0000   30.0000 -120.0000 25

#__ type_ start__ end____ width___ exp.time_
 26 omega   48.00   88.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.3609 -125.0000 -180.0000 40

#__ type_ start__ end____ width___ exp.time_
 27 omega   30.00   55.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.3609  -30.0000 -150.0000 25

#__ type_ start__ end____ width___ exp.time_
 28 omega   92.00  134.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.3609   45.0000 -180.0000 42

#__ type_ start__ end____ width___ exp.time_
 29 omega   94.00  120.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.3609 -125.0000 -180.0000 26

#__ type_ start__ end____ width___ exp.time_
 30 omega   97.00  124.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.3609  -77.0000    0.0000 27

#__ type_ start__ end____ width___ exp.time_
 31 omega -115.00  -11.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.5756  -57.0000   60.0000 104

#__ type_ start__ end____ width___ exp.time_
 32 omega -119.00   -7.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.5756  -77.0000 -150.0000 112

#__ type_ start__ end____ width___ exp.time_
 33 omega -115.00  -11.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.5756  -57.0000 -120.0000 104

#__ type_ start__ end____ width___ exp.time_
 34 omega    7.00  119.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       40.5756   77.0000    0.0000 112

#__ type_ start__ end____ width___ exp.time_
 35 omega    7.00  119.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       40.5756   77.0000 -180.0000 112

#__ type_ start__ end____ width___ exp.time_
 36 omega    2.00   98.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       40.5756 -125.0000  -90.0000 96

#__ type_ start__ end____ width___ exp.time_
 37 omega -162.00  -49.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -83.0000  -77.0000 -120.0000 113

#__ type_ start__ end____ width___ exp.time_
 38 omega -162.00  -49.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -83.0000  -77.0000  -90.0000 113

#__ type_ start__ end____ width___ exp.time_
 39 omega -162.00  -49.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -83.0000  -77.0000 -150.0000 113

#__ type_ start__ end____ width___ exp.time_
 40 omega -162.00  -49.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -83.0000  -77.0000   60.0000 113

#__ type_ start__ end____ width___ exp.time_
 41 omega -162.00  -49.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -83.0000  -77.0000  -30.0000 113

#__ type_ start__ end____ width___ exp.time_
 42 omega -162.00  -49.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -83.0000  -77.0000   90.0000 113

#__ type_ start__ end____ width___ exp.time_
 43 omega -157.00  -53.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -83.0000  -61.0000   90.0000 104

#__ type_ start__ end____ width___ exp.time_
 44 omega -162.00  -49.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -83.0000  -77.0000   30.0000 113

#__ type_ start__ end____ width___ exp.time_
 45 omega -162.00  -49.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -83.0000  -77.0000 -180.0000 113

#__ type_ start__ end____ width___ exp.time_
 46 omega -162.00  -49.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -83.0000  -77.0000  150.0000 113

#__ type_ start__ end____ width___ exp.time_
 47 omega -162.00  -49.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -83.0000  -77.0000    0.0000 113

#__ type_ start__ end____ width___ exp.time_
 48 omega -162.00  -49.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -83.0000  -77.0000  -60.0000 113

#__ type_ start__ end____ width___ exp.time_
 49 omega   78.00  158.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.3609   30.0000   30.0000 80

#__ type_ start__ end____ width___ exp.time_
 50 omega   30.00   69.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.3609  -30.0000  120.0000 39

#__ type_ start__ end____ width___ exp.time_
 51 omega   78.00  158.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.3609   61.0000  120.0000 80

#__ type_ start__ end____ width___ exp.time_
 52 omega   75.00  158.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.3609   77.0000   30.0000 83

#__ type_ start__ end____ width___ exp.time_
 53 omega   75.00  158.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.3609   77.0000  -90.0000 83

#__ type_ start__ end____ width___ exp.time_
 54 omega   75.00  158.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.3609   77.0000 -120.0000 83

#__ type_ start__ end____ width___ exp.time_
 55 omega -115.00  -11.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.5756  -57.0000  -60.0000 104

#__ type_ start__ end____ width___ exp.time_
 56 omega  -49.00  130.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       40.5756    0.0000 -120.0000 179

#__ type_ start__ end____ width___ exp.time_
 57 omega    7.00  119.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       40.5756   77.0000   90.0000 112

#__ type_ start__ end____ width___ exp.time_
 58 omega  -49.00  130.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       40.5756    0.0000  -90.0000 179

#__ type_ start__ end____ width___ exp.time_
 59 omega  -49.00  130.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       40.5756    0.0000 -180.0000 179

#__ type_ start__ end____ width___ exp.time_
 60 omega  -49.00  130.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       40.5756    0.0000 -150.0000 179

#__ type_ start__ end____ width___ exp.time_
 61 omega -162.00  -49.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -83.0000  -77.0000  120.0000 113

#__ type_ start__ end____ width___ exp.time_
 62 omega   75.00  158.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.3609   77.0000 -150.0000 83

#__ type_ start__ end____ width___ exp.time_
 63 omega   75.00  158.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.3609   77.0000  150.0000 83

#__ type_ start__ end____ width___ exp.time_
 64 omega   75.00  158.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.3609   77.0000   60.0000 83

#__ type_ start__ end____ width___ exp.time_
 65 omega   78.00  158.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.3609   61.0000  -60.0000 80

#__ type_ start__ end____ width___ exp.time_
 66 omega   78.00  158.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.3609   61.0000   30.0000 80

#__ type_ start__ end____ width___ exp.time_
 67 omega   81.00  158.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.3609   45.0000   30.0000 77

#__ type_ start__ end____ width___ exp.time_
 68 omega   31.00   69.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.3609  -34.0000   20.0000 38

#__ type_ start__ end____ width___ exp.time_
 69 omega   78.00  158.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.3609   61.0000 -180.0000 80

#__ type_ start__ end____ width___ exp.time_
 70 omega   75.00  158.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.3609   77.0000 -180.0000 83

#__ type_ start__ end____ width___ exp.time_
 71 omega   34.00   77.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.3609  -45.0000  120.0000 43

#__ type_ start__ end____ width___ exp.time_
 72 omega   78.00  158.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.3609   61.0000  -30.0000 80

#__ type_ start__ end____ width___ exp.time_
 73 omega   75.00  158.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.3609   77.0000   90.0000 83

#__ type_ start__ end____ width___ exp.time_
 74 omega   78.00  158.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.3609   61.0000   60.0000 80

#__ type_ start__ end____ width___ exp.time_
 75 omega   78.00  158.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.3609   61.0000  150.0000 80

#__ type_ start__ end____ width___ exp.time_
 76 omega   75.00  146.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.3609   77.0000  -60.0000 71

#__ type_ start__ end____ width___ exp.time_
 77 omega   75.00  158.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.3609   77.0000  -30.0000 83

;

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       'CrysAlis Pro (Oxford Diffraction Ltd., 2011)'
_computing_cell_refinement       'CrysAlis Pro (Oxford Diffraction Ltd., 2011)'
_computing_data_reduction        'CrysAlis Pro (Oxford Diffraction Ltd., 2011)'
_computing_structure_solution    'OLEX2 (Dolomanov et al, 2009)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Diamond v.3.2f (Crystal Impact GbR, 2008)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION
#----------------------------------------------------------------------------#

_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_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 > 2σ(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)+(0.0481P)²+0.0651P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    noref
_refine_ls_extinction_method     none
_refine_ls_number_reflns         2281
_refine_ls_number_parameters     163
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0267
_refine_ls_R_factor_gt           0.0266
_refine_ls_wR_factor_ref         0.0716
_refine_ls_wR_factor_gt          0.0714
_refine_ls_goodness_of_fit_ref   1.073
_refine_ls_restrained_S_all      1.073
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_ls_abs_structure_details 
;
The Friedel pair coverage of the experiment is almost complete (99%).
Analysis of the absolute structure using likelihood methods
(Hooft, Straver & Spek, 2008) was performed using PLATON (Spek, 2011).
 The results indicated that the absolute structure had been correctly
 assigned. The method calculated that the probability that the structure 
is inverted is smaller than 10-73. The absolute structure parameter y 
(Hooft, Straver & Spek, 2008) was calculated using PLATON (Spek,
2010). The resulting value was y=0.10(5), which together with Flack parameter 
value, indicate that the absolute structure has sureley been determined 
correctly.

Flack, H. D. (1983), Acta Cryst. A39, 876-881
Flack & G. Bernardinelli, Acta Cryst. 1999, A55, 908-915; 
H. D. Flack & G. Bernardinelli, J. Appl. Cryst. 2000, 33, 1143-1148.

R. W. W. Hooft, L. H. Straver & A. L. Spek, J. Appl. Cryst. 2008, 41, 96-103
A. L. Spek (2010) PLATON, Utrecht, The Netherlands; 
A. L. Spek, J. Appl. Cryst. 2003, 36, 7-13
A. L. Thompson & D. J. Watkin, Tetrahedron: Asymmetry 2009, 20, 712--717

;
_refine_ls_abs_structure_Flack   -0.03(13)
_refine_diff_density_max         0.21
_refine_diff_density_min         -0.168
_refine_diff_density_rms         0.035

#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

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 0 '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'

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
O2 O 0.14095(9) 0.38450(14) 0.24257(8) 0.01966(19) Uani 1 1 d . . .
O1 O 0.58047(9) -0.12905(18) 0.40984(9) 0.0297(2) Uani 1 1 d . . .
O3 O 0.37800(9) 0.27544(16) 0.23293(8) 0.0231(2) Uani 1 1 d . . .
O4 O -0.05956(10) 0.17794(15) 0.48770(9) 0.0269(2) Uani 1 1 d . . .
C11 C -0.28512(12) 0.2055(2) -0.00994(11) 0.0219(3) Uani 1 1 d . . .
H11 H -0.3325 0.1146 -0.0721 0.026 Uiso 1 1 calc R . .
C6 C 0.25955(12) 0.30500(19) 0.31601(11) 0.0177(2) Uani 1 1 d . . .
H6 H 0.2871 0.4144 0.3836 0.021 Uiso 1 1 calc R . .
C10 C -0.15288(12) 0.1380(2) 0.04683(11) 0.0189(2) Uani 1 1 d . . .
H10 H -0.1097 0.0019 0.0223 0.023 Uiso 1 1 calc R . .
C14 C -0.14869(13) 0.4664(2) 0.17578(12) 0.0208(2) Uani 1 1 d . . .
H14 H -0.1038 0.5547 0.2405 0.025 Uiso 1 1 calc R . .
C13 C -0.28001(14) 0.5350(2) 0.11727(13) 0.0241(3) Uani 1 1 d . . .
H13 H -0.3233 0.6714 0.1414 0.029 Uiso 1 1 calc R . .
C8 C -0.06484(12) 0.07512(19) 0.39033(11) 0.0192(2) Uani 1 1 d . . .
H8 H -0.1568 0.0163 0.3628 0.023 Uiso 1 1 calc R . .
C9 C -0.08367(12) 0.2687(2) 0.13927(10) 0.0164(2) Uani 1 1 d . . .
C1 C 0.47999(12) -0.0230(2) 0.36194(11) 0.0198(2) Uani 1 1 d . . .
C5 C 0.06232(12) 0.19379(19) 0.19438(11) 0.0161(2) Uani 1 1 d . . .
H5 H 0.1194 0.1251 0.1259 0.019 Uiso 1 1 calc R . .
C3 C 0.21303(11) 0.08263(18) 0.37470(11) 0.0146(2) Uani 1 1 d . . .
H3 H 0.1997 0.1035 0.467 0.018 Uiso 1 1 calc R . .
C4 C 0.06393(12) 0.03269(17) 0.30867(10) 0.0150(2) Uani 1 1 d . . .
H4 H 0.0617 -0.1247 0.2783 0.018 Uiso 1 1 calc R . .
C2 C 0.32448(12) -0.1032(2) 0.35464(11) 0.0189(2) Uani 1 1 d . . .
H2A H 0.3119 -0.2196 0.4192 0.023 Uiso 1 1 calc R . .
H2B H 0.3044 -0.1716 0.2711 0.023 Uiso 1 1 calc R . .
C12 C -0.34760(13) 0.4060(2) 0.02442(12) 0.0237(3) Uani 1 1 d . . .
H12 H -0.4364 0.4544 -0.0157 0.028 Uiso 1 1 calc R . .
C7 C 0.50530(12) 0.1995(2) 0.30057(12) 0.0226(3) Uani 1 1 d . . .
H7A H 0.5338 0.3098 0.3661 0.027 Uiso 1 1 calc R . .
H7B H 0.5867 0.1864 0.2422 0.027 Uiso 1 1 calc R . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_geom_special_details            
;
 All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell s.u.'s are taken
 into account individually in the estimation of s.u.'s in distances, angles
 and torsion angles; correlations between s.u.'s in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell s.u.'s is used for estimating s.u.'s 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
O2 C6 1.3987(13) . ?
O2 C5 1.4388(13) . ?
O1 C1 1.2161(15) . ?
O3 C7 1.4228(14) . ?
O3 C6 1.4344(14) . ?
O4 C8 1.2048(16) . ?
C11 C12 1.3893(19) . ?
C11 C10 1.3941(16) . ?
C11 H11 0.95 . ?
C6 C3 1.5422(15) . ?
C6 H6 1 . ?
C10 C9 1.3927(16) . ?
C10 H10 0.95 . ?
C14 C9 1.3916(16) . ?
C14 C13 1.3963(17) . ?
C14 H14 0.95 . ?
C13 C12 1.3836(19) . ?
C13 H13 0.95 . ?
C8 C4 1.5111(15) . ?
C8 H8 0.95 . ?
C9 C5 1.5092(15) . ?
C1 C2 1.5033(15) . ?
C1 C7 1.5103(18) . ?
C5 C4 1.5531(15) . ?
C5 H5 1 . ?
C3 C2 1.5338(15) . ?
C3 C4 1.5422(14) . ?
C3 H3 1 . ?
C4 H4 1 . ?
C2 H2A 0.99 . ?
C2 H2B 0.99 . ?
C12 H12 0.95 . ?
C7 H7A 0.99 . ?
C7 H7B 0.99 . ?

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
C6 O2 C5 107.14(9) . . ?
C7 O3 C6 110.70(9) . . ?
C12 C11 C10 119.94(12) . . ?
C12 C11 H11 120 . . ?
C10 C11 H11 120 . . ?
O2 C6 O3 106.79(9) . . ?
O2 C6 C3 107.55(8) . . ?
O3 C6 C3 111.56(9) . . ?
O2 C6 H6 110.3 . . ?
O3 C6 H6 110.3 . . ?
C3 C6 H6 110.3 . . ?
C9 C10 C11 120.46(11) . . ?
C9 C10 H10 119.8 . . ?
C11 C10 H10 119.8 . . ?
C9 C14 C13 119.93(12) . . ?
C9 C14 H14 120 . . ?
C13 C14 H14 120 . . ?
C12 C13 C14 120.52(12) . . ?
C12 C13 H13 119.7 . . ?
C14 C13 H13 119.7 . . ?
O4 C8 C4 124.87(11) . . ?
O4 C8 H8 117.6 . . ?
C4 C8 H8 117.6 . . ?
C14 C9 C10 119.37(10) . . ?
C14 C9 C5 121.95(10) . . ?
C10 C9 C5 118.66(10) . . ?
O1 C1 C2 123.71(11) . . ?
O1 C1 C7 121.31(10) . . ?
C2 C1 C7 114.95(10) . . ?
O2 C5 C9 108.98(9) . . ?
O2 C5 C4 103.22(8) . . ?
C9 C5 C4 118.21(9) . . ?
O2 C5 H5 108.7 . . ?
C9 C5 H5 108.7 . . ?
C4 C5 H5 108.7 . . ?
C2 C3 C6 112.38(9) . . ?
C2 C3 C4 112.20(9) . . ?
C6 C3 C4 103.78(8) . . ?
C2 C3 H3 109.4 . . ?
C6 C3 H3 109.4 . . ?
C4 C3 H3 109.4 . . ?
C8 C4 C3 113.76(9) . . ?
C8 C4 C5 110.98(9) . . ?
C3 C4 C5 102.55(8) . . ?
C8 C4 H4 109.8 . . ?
C3 C4 H4 109.8 . . ?
C5 C4 H4 109.8 . . ?
C1 C2 C3 113.17(10) . . ?
C1 C2 H2A 108.9 . . ?
C3 C2 H2A 108.9 . . ?
C1 C2 H2B 108.9 . . ?
C3 C2 H2B 108.9 . . ?
H2A C2 H2B 107.8 . . ?
C13 C12 C11 119.74(11) . . ?
C13 C12 H12 120.1 . . ?
C11 C12 H12 120.1 . . ?
O3 C7 C1 111.52(9) . . ?
O3 C7 H7A 109.3 . . ?
C1 C7 H7A 109.3 . . ?
O3 C7 H7B 109.3 . . ?
C1 C7 H7B 109.3 . . ?
H7A C7 H7B 108 . . ?

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
C5 O2 C6 O3 88.57(10) . . . . ?
C5 O2 C6 C3 -31.30(11) . . . . ?
C7 O3 C6 O2 178.59(9) . . . . ?
C7 O3 C6 C3 -64.16(12) . . . . ?
C12 C11 C10 C9 0.92(17) . . . . ?
C9 C14 C13 C12 1.06(18) . . . . ?
C13 C14 C9 C10 -1.80(17) . . . . ?
C13 C14 C9 C5 176.49(11) . . . . ?
C11 C10 C9 C14 0.82(17) . . . . ?
C11 C10 C9 C5 -177.53(10) . . . . ?
C6 O2 C5 C9 167.48(9) . . . . ?
C6 O2 C5 C4 41.01(11) . . . . ?
C14 C9 C5 O2 -22.94(14) . . . . ?
C10 C9 C5 O2 155.37(10) . . . . ?
C14 C9 C5 C4 94.38(13) . . . . ?
C10 C9 C5 C4 -87.32(13) . . . . ?
O2 C6 C3 C2 129.80(10) . . . . ?
O3 C6 C3 C2 13.00(13) . . . . ?
O2 C6 C3 C4 8.35(11) . . . . ?
O3 C6 C3 C4 -108.44(9) . . . . ?
O4 C8 C4 C3 14.09(16) . . . . ?
O4 C8 C4 C5 -100.95(13) . . . . ?
C2 C3 C4 C8 133.93(10) . . . . ?
C6 C3 C4 C8 -104.50(10) . . . . ?
C2 C3 C4 C5 -106.15(10) . . . . ?
C6 C3 C4 C5 15.41(10) . . . . ?
O2 C5 C4 C8 88.13(10) . . . . ?
C9 C5 C4 C8 -32.21(13) . . . . ?
O2 C5 C4 C3 -33.70(10) . . . . ?
C9 C5 C4 C3 -154.04(9) . . . . ?
O1 C1 C2 C3 142.05(12) . . . . ?
C7 C1 C2 C3 -40.02(14) . . . . ?
C6 C3 C2 C1 36.63(13) . . . . ?
C4 C3 C2 C1 153.13(9) . . . . ?
C14 C13 C12 C11 0.69(18) . . . . ?
C10 C11 C12 C13 -1.67(17) . . . . ?
C6 O3 C7 C1 61.38(13) . . . . ?
O1 C1 C7 O3 170.19(11) . . . . ?
C2 C1 C7 O3 -7.79(15) . . . . ?

# The following lines are used to test the character set of files sent by
# network email or other means. They are not part of the CIF data set
# abcdefghijklmnopqrstuvwxyzABCDEFGHIJKLMNOPQRSTUVWXYZ0123456789
# !@#$%^&*()_+{}:"~<>?|\-=[];'`,./

# END of CIF
####################################################################### 
# 
# 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_a2014049_ao509_rem
_database_code_depnum_ccdc_archive 'CCDC 1525189'
_audit_update_record             
;
2017-01-02 deposited with the CCDC.
2017-01-30 downloaded from the CCDC.
;

_audit_creation_date             2014-06-09T23:07:07-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_name_systematic        
;
 (2R,3S,3aR,7aS)-5-Oxo-2-pentylhexahydro-4H-furo[2,3-b]pyran-3-carbaldehyde
;
_chemical_formula_moiety         'C13 H20 O4'
_chemical_formula_sum            'C13 H20 O4'
_chemical_formula_weight         240.29
_chemical_compound_source        'synthesis as described'
_chemical_absolute_configuration 2R,3S,3aR,7aS

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'P 21 21 21'
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_Int_Tables_number      19
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                   5.56040(10)
_cell_length_b                   6.68950(10)
_cell_length_c                   33.0826(5)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1230.55(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9940
_cell_measurement_theta_min      5.324
_cell_measurement_theta_max      73.683
_cell_measurement_wavelength     1.54184

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.1821
_exptl_crystal_size_mid          0.0405
_exptl_crystal_size_min          0.0323
_exptl_crystal_density_diffrn    1.297
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             520
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
4 0 5 0.0052
0 -4 -4 0.0772
-4 0 -5 0.0275
-1 4 3 0.0925
0 0 21 0.0084
0 0 -21 0.0235

_exptl_special_details           
;
 ?
;

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    0.779
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   
;
        CrysAlisPro, Agilent Technologies,
        Version 1.171.36.24 (release 03-12-2012 CrysAlis171 .NET)
        (compiled Dec  3 2012,18:21:49)
Analytical numeric absorption correction using a multifaceted crystal
                        model based on expressions derived by R.C. Clark & J.S.
        (Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
;
_exptl_absorpt_correction_T_min  0.921
_exptl_absorpt_correction_T_max  0.979

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'Nova (Cu) X-ray micro-source'
_diffrn_radiation_monochromator  'Multilayer optics'
_diffrn_source_voltage           50
_diffrn_source_current           0.8
_diffrn_source_power             0.04
_diffrn_radiation_probe          x-ray
_diffrn_measurement_device_type  'Agilent SuperNova'
_diffrn_measurement_method       'ω scans'
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            Atlas
_diffrn_measurement_device       'κ-geometry diffractometer'
_diffrn_detector_area_resol_mean 5.2012
_diffrn_orient_matrix_ub_11      -0.0233104
_diffrn_orient_matrix_ub_12      -0.1098188
_diffrn_orient_matrix_ub_13      0.0407522
_diffrn_orient_matrix_ub_21      0.10786
_diffrn_orient_matrix_ub_22      -0.1897494
_diffrn_orient_matrix_ub_23      -0.0191726
_diffrn_orient_matrix_ub_31      0.2541132
_diffrn_orient_matrix_ub_32      0.0704332
_diffrn_orient_matrix_ub_33      0.0118727
_diffrn_reflns_av_R_equivalents  0.0418
_diffrn_reflns_av_unetI/netI     0.0191
_diffrn_reflns_number            22597
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -40
_diffrn_reflns_limit_l_max       40
_diffrn_reflns_theta_min         2.67
_diffrn_reflns_theta_max         71
_diffrn_reflns_theta_full        71
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_reflns_number_total             2369
_reflns_number_gt                2283
_reflns_threshold_expression     >2σ(I)
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -82.00  -12.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.9506  125.0000  150.0000 70

#__ type_ start__ end____ width___ exp.time_
  2 omega   18.00   78.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       40.9506   37.0000 -150.0000 60

#__ type_ start__ end____ width___ exp.time_
  3 omega   83.00  109.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       40.9506   37.0000 -150.0000 26

#__ type_ start__ end____ width___ exp.time_
  4 omega  -34.00   -8.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      -83.0000   45.0000   30.0000 26

#__ type_ start__ end____ width___ exp.time_
  5 omega   90.00  116.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      108.3609 -125.0000 -150.0000 26

#__ type_ start__ end____ width___ exp.time_
  6 omega   94.00  153.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      108.3609   30.0000   30.0000 59

#__ type_ start__ end____ width___ exp.time_
  7 omega   38.00   69.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      108.3609  -30.0000    0.0000 31

#__ type_ start__ end____ width___ exp.time_
  8 omega   35.00   61.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      108.3609  -30.0000   30.0000 26

#__ type_ start__ end____ width___ exp.time_
  9 omega   43.00   81.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      108.3609 -125.0000 -150.0000 38

#__ type_ start__ end____ width___ exp.time_
 10 omega   65.00  111.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      108.3609 -100.0000    7.0000 46

#__ type_ start__ end____ width___ exp.time_
 11 omega   33.00  150.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      108.3609  -15.0000 -180.0000 117

#__ type_ start__ end____ width___ exp.time_
 12 omega   31.00   69.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      108.3609  -30.0000   60.0000 38

#__ type_ start__ end____ width___ exp.time_
 13 omega  -53.00   23.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.9506   37.0000  120.0000 76

#__ type_ start__ end____ width___ exp.time_
 14 omega    7.00  107.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       40.9506   77.0000  -60.0000 100

#__ type_ start__ end____ width___ exp.time_
 15 omega  -76.00  -50.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      -83.0000   45.0000  120.0000 26

#__ type_ start__ end____ width___ exp.time_
 16 omega   75.00  126.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      108.3609  -77.0000   30.0000 51

#__ type_ start__ end____ width___ exp.time_
 17 omega   67.00  104.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      108.3609 -125.0000  -60.0000 37

#__ type_ start__ end____ width___ exp.time_
 18 omega   35.00   61.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      108.3609  -77.0000   30.0000 26

#__ type_ start__ end____ width___ exp.time_
 19 omega   70.00  139.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      108.3609  -61.0000  120.0000 69

#__ type_ start__ end____ width___ exp.time_
 20 omega   34.00   60.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      108.3609  -61.0000  120.0000 26

#__ type_ start__ end____ width___ exp.time_
 21 omega   34.00  105.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      108.3609  -94.0000  -60.0000 71

#__ type_ start__ end____ width___ exp.time_
 22 omega   30.00   55.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      108.3609  -30.0000  -60.0000 25

#__ type_ start__ end____ width___ exp.time_
 23 omega   43.00   68.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      108.3609  -45.0000  -90.0000 25

#__ type_ start__ end____ width___ exp.time_
 24 omega   60.00  133.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      108.3609   15.0000 -120.0000 73

#__ type_ start__ end____ width___ exp.time_
 25 omega   43.00   73.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      108.3609  -45.0000  -60.0000 30

#__ type_ start__ end____ width___ exp.time_
 26 omega -120.00   -7.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.9506  -77.0000  120.0000 113

#__ type_ start__ end____ width___ exp.time_
 27 omega -117.00  -15.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.9506  -37.0000  -30.0000 102

#__ type_ start__ end____ width___ exp.time_
 28 omega   11.00  115.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       40.9506   57.0000 -120.0000 104

#__ type_ start__ end____ width___ exp.time_
 29 omega    2.00   98.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       40.9506 -125.0000  -30.0000 96

#__ type_ start__ end____ width___ exp.time_
 30 omega   11.00  115.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       40.9506   57.0000   90.0000 104

#__ type_ start__ end____ width___ exp.time_
 31 omega -157.00  -53.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      -83.0000  -61.0000 -180.0000 104

#__ type_ start__ end____ width___ exp.time_
 32 omega -162.00  -49.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      -83.0000  -77.0000   90.0000 113

#__ type_ start__ end____ width___ exp.time_
 33 omega -162.00  -49.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      -83.0000  -77.0000  -30.0000 113

#__ type_ start__ end____ width___ exp.time_
 34 omega -162.00  -49.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      -83.0000  -77.0000 -120.0000 113

#__ type_ start__ end____ width___ exp.time_
 35 omega -162.00  -49.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      -83.0000  -77.0000  150.0000 113

#__ type_ start__ end____ width___ exp.time_
 36 omega -162.00  -49.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      -83.0000  -77.0000   30.0000 113

#__ type_ start__ end____ width___ exp.time_
 37 omega -162.00  -49.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      -83.0000  -77.0000  -90.0000 113

#__ type_ start__ end____ width___ exp.time_
 38 omega   30.00   69.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      108.3609  -30.0000  -30.0000 39

#__ type_ start__ end____ width___ exp.time_
 39 omega   81.00  158.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      108.3609   45.0000  -90.0000 77

#__ type_ start__ end____ width___ exp.time_
 40 omega   78.00  158.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      108.3609   30.0000  -30.0000 80

#__ type_ start__ end____ width___ exp.time_
 41 omega   75.00  144.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      108.3609   77.0000   30.0000 69

#__ type_ start__ end____ width___ exp.time_
 42 omega   78.00  158.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      108.3609   61.0000  150.0000 80

#__ type_ start__ end____ width___ exp.time_
 43 omega   75.00  158.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      108.3609   77.0000  -30.0000 83

#__ type_ start__ end____ width___ exp.time_
 44 omega   78.00  158.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      108.3609   61.0000   90.0000 80

;

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       'CrysAlis Pro (Oxford Diffraction Ltd., 2011)'
_computing_cell_refinement       'CrysAlis Pro (Oxford Diffraction Ltd., 2011)'
_computing_data_reduction        'CrysAlis Pro (Oxford Diffraction Ltd., 2011)'
_computing_structure_solution    'OLEX2 (Dolomanov et al, 2009)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Diamond v.3.2f (Crystal Impact GbR, 2008)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION
#----------------------------------------------------------------------------#

_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_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 > 2σ(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)+(0.0294P)²+0.3652P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    noref
_refine_ls_extinction_method     none
_refine_ls_number_reflns         2369
_refine_ls_number_parameters     155
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0327
_refine_ls_R_factor_gt           0.0306
_refine_ls_wR_factor_ref         0.0711
_refine_ls_wR_factor_gt          0.0702
_refine_ls_goodness_of_fit_ref   1.088
_refine_ls_restrained_S_all      1.088
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_ls_abs_structure_details 
;
The Friedel pair coverage of the experiment is almost complete (99%).
Analysis of the absolute structure using likelihood methods
(Hooft, Straver & Spek, 2008) was performed using PLATON (Spek, 2011).
 The results indicated that the absolute structure had been correctly
 assigned. The method calculated that the probability that the structure 
is inverted is smaller than 10-51. The absolute structure parameter y 
(Hooft, Straver & Spek, 2008) was calculated using PLATON (Spek,
2010). The resulting value was y=-0.12(7), which together with Flack parameter 
value, indicate that the absolute structure has sureley been determined 
correctly.

Flack, H. D. (1983), Acta Cryst. A39, 876-881
Flack & G. Bernardinelli, Acta Cryst. 1999, A55, 908-915; 
H. D. Flack & G. Bernardinelli, J. Appl. Cryst. 2000, 33, 1143-1148.

R. W. W. Hooft, L. H. Straver & A. L. Spek, J. Appl. Cryst. 2008, 41, 96-103
A. L. Spek (2010) PLATON, Utrecht, The Netherlands; 
A. L. Spek, J. Appl. Cryst. 2003, 36, 7-13
A. L. Thompson & D. J. Watkin, Tetrahedron: Asymmetry 2009, 20, 712--717

;
_refine_ls_abs_structure_Flack   -0.13(18)
_refine_diff_density_max         0.177
_refine_diff_density_min         -0.156
_refine_diff_density_rms         0.033

#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

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 0 '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'

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 0.8012(2) 0.8866(2) 0.25261(3) 0.0337(3) Uani 1 1 d . . .
O2 O 0.9841(2) 0.57225(14) 0.10887(3) 0.0186(2) Uani 1 1 d . . .
O3 O 1.12197(19) 0.72001(16) 0.16600(3) 0.0209(2) Uani 1 1 d . . .
O4 O 0.5758(2) 0.13110(16) 0.16722(4) 0.0301(3) Uani 1 1 d . . .
C1 C 0.8578(3) 0.7984(2) 0.22197(4) 0.0216(3) Uani 1 1 d . . .
C2 C 0.7245(3) 0.6226(2) 0.20474(4) 0.0197(3) Uani 1 1 d . . .
H2A H 0.5659 0.6102 0.2181 0.024 Uiso 1 1 calc R . .
H2B H 0.8164 0.4985 0.21 0.024 Uiso 1 1 calc R . .
C3 C 0.6891(3) 0.6497(2) 0.15891(4) 0.0154(3) Uani 1 1 d . . .
H3 H 0.5613 0.7517 0.1537 0.018 Uiso 1 1 calc R . .
C4 C 0.6267(3) 0.4526(2) 0.13655(4) 0.0157(3) Uani 1 1 d . . .
H4 H 0.5178 0.4856 0.1134 0.019 Uiso 1 1 calc R . .
C5 C 0.8680(3) 0.3863(2) 0.11935(4) 0.0164(3) Uani 1 1 d . . .
H5 H 0.9629 0.3183 0.141 0.02 Uiso 1 1 calc R . .
C6 C 0.9270(3) 0.7146(2) 0.13827(4) 0.0162(3) Uani 1 1 d . . .
H6 H 0.9063 0.8487 0.1254 0.019 Uiso 1 1 calc R . .
C7 C 1.0757(3) 0.8602(2) 0.19761(5) 0.0247(3) Uani 1 1 d . . .
H7A H 1.0482 0.9942 0.1858 0.03 Uiso 1 1 calc R . .
H7B H 1.2176 0.8685 0.2156 0.03 Uiso 1 1 calc R . .
C8 C 0.5031(3) 0.2997(2) 0.16265(4) 0.0191(3) Uani 1 1 d . . .
H8 H 0.3599 0.3379 0.1763 0.023 Uiso 1 1 calc R . .
C9 C 0.8631(3) 0.2551(2) 0.08222(4) 0.0186(3) Uani 1 1 d . . .
H9A H 0.7891 0.3302 0.0596 0.022 Uiso 1 1 calc R . .
H9B H 0.761 0.1368 0.0877 0.022 Uiso 1 1 calc R . .
C10 C 1.1130(3) 0.1847(2) 0.06947(4) 0.0199(3) Uani 1 1 d . . .
H10A H 1.1908 0.1179 0.0928 0.024 Uiso 1 1 calc R . .
H10B H 1.2113 0.303 0.0624 0.024 Uiso 1 1 calc R . .
C11 C 1.1114(3) 0.0409(2) 0.03363(4) 0.0207(3) Uani 1 1 d . . .
H11A H 1.0538 0.1127 0.0093 0.025 Uiso 1 1 calc R . .
H11B H 0.9973 -0.0692 0.0393 0.025 Uiso 1 1 calc R . .
C12 C 1.3603(3) -0.0477(2) 0.02487(4) 0.0214(3) Uani 1 1 d . . .
H12A H 1.3584 -0.1106 -0.0022 0.026 Uiso 1 1 calc R . .
H12B H 1.4803 0.0616 0.0244 0.026 Uiso 1 1 calc R . .
C13 C 1.4370(3) -0.2023(2) 0.05587(5) 0.0250(3) Uani 1 1 d . . .
H13A H 1.5972 -0.2528 0.049 0.038 Uiso 1 1 calc R . .
H13B H 1.3218 -0.3132 0.0559 0.038 Uiso 1 1 calc R . .
H13C H 1.4414 -0.1406 0.0827 0.038 Uiso 1 1 calc R . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_geom_special_details            
;
 All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell s.u.'s are taken
 into account individually in the estimation of s.u.'s in distances, angles
 and torsion angles; correlations between s.u.'s in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell s.u.'s is used for estimating s.u.'s 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 1.2144(18) . ?
O2 C6 1.3978(16) . ?
O2 C5 1.4436(17) . ?
O3 C6 1.4207(17) . ?
O3 C7 1.4278(17) . ?
O4 C8 1.2079(18) . ?
C1 C2 1.502(2) . ?
C1 C7 1.513(2) . ?
C2 C3 1.5396(19) . ?
C2 H2A 0.99 . ?
C2 H2B 0.99 . ?
C3 C6 1.5510(19) . ?
C3 C4 1.5512(19) . ?
C3 H3 1 . ?
C4 C8 1.505(2) . ?
C4 C5 1.524(2) . ?
C4 H4 1 . ?
C5 C9 1.5101(19) . ?
C5 H5 1 . ?
C6 H6 1 . ?
C7 H7A 0.99 . ?
C7 H7B 0.99 . ?
C8 H8 0.95 . ?
C9 C10 1.526(2) . ?
C9 H9A 0.99 . ?
C9 H9B 0.99 . ?
C10 C11 1.5269(19) . ?
C10 H10A 0.99 . ?
C10 H10B 0.99 . ?
C11 C12 1.533(2) . ?
C11 H11A 0.99 . ?
C11 H11B 0.99 . ?
C12 C13 1.517(2) . ?
C12 H12A 0.99 . ?
C12 H12B 0.99 . ?
C13 H13A 0.98 . ?
C13 H13B 0.98 . ?
C13 H13C 0.98 . ?

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
C6 O2 C5 108.57(10) . . ?
C6 O3 C7 110.62(11) . . ?
O1 C1 C2 124.70(14) . . ?
O1 C1 C7 121.28(14) . . ?
C2 C1 C7 114.02(12) . . ?
C1 C2 C3 110.17(12) . . ?
C1 C2 H2A 109.6 . . ?
C3 C2 H2A 109.6 . . ?
C1 C2 H2B 109.6 . . ?
C3 C2 H2B 109.6 . . ?
H2A C2 H2B 108.1 . . ?
C2 C3 C6 110.95(11) . . ?
C2 C3 C4 113.49(11) . . ?
C6 C3 C4 102.65(11) . . ?
C2 C3 H3 109.8 . . ?
C6 C3 H3 109.8 . . ?
C4 C3 H3 109.8 . . ?
C8 C4 C5 114.78(12) . . ?
C8 C4 C3 113.95(11) . . ?
C5 C4 C3 103.20(11) . . ?
C8 C4 H4 108.2 . . ?
C5 C4 H4 108.2 . . ?
C3 C4 H4 108.2 . . ?
O2 C5 C9 108.28(11) . . ?
O2 C5 C4 103.46(11) . . ?
C9 C5 C4 117.18(12) . . ?
O2 C5 H5 109.2 . . ?
C9 C5 H5 109.2 . . ?
C4 C5 H5 109.2 . . ?
O2 C6 O3 107.07(11) . . ?
O2 C6 C3 108.00(11) . . ?
O3 C6 C3 111.93(10) . . ?
O2 C6 H6 109.9 . . ?
O3 C6 H6 109.9 . . ?
C3 C6 H6 109.9 . . ?
O3 C7 C1 110.79(12) . . ?
O3 C7 H7A 109.5 . . ?
C1 C7 H7A 109.5 . . ?
O3 C7 H7B 109.5 . . ?
C1 C7 H7B 109.5 . . ?
H7A C7 H7B 108.1 . . ?
O4 C8 C4 123.61(14) . . ?
O4 C8 H8 118.2 . . ?
C4 C8 H8 118.2 . . ?
C5 C9 C10 112.79(12) . . ?
C5 C9 H9A 109 . . ?
C10 C9 H9A 109 . . ?
C5 C9 H9B 109 . . ?
C10 C9 H9B 109 . . ?
H9A C9 H9B 107.8 . . ?
C9 C10 C11 113.81(12) . . ?
C9 C10 H10A 108.8 . . ?
C11 C10 H10A 108.8 . . ?
C9 C10 H10B 108.8 . . ?
C11 C10 H10B 108.8 . . ?
H10A C10 H10B 107.7 . . ?
C10 C11 C12 112.67(13) . . ?
C10 C11 H11A 109.1 . . ?
C12 C11 H11A 109.1 . . ?
C10 C11 H11B 109.1 . . ?
C12 C11 H11B 109.1 . . ?
H11A C11 H11B 107.8 . . ?
C13 C12 C11 112.92(13) . . ?
C13 C12 H12A 109 . . ?
C11 C12 H12A 109 . . ?
C13 C12 H12B 109 . . ?
C11 C12 H12B 109 . . ?
H12A C12 H12B 107.8 . . ?
C12 C13 H13A 109.5 . . ?
C12 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C12 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 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
O1 C1 C2 C3 133.97(16) . . . . ?
C7 C1 C2 C3 -46.11(17) . . . . ?
C1 C2 C3 C6 47.13(16) . . . . ?
C1 C2 C3 C4 162.10(12) . . . . ?
C2 C3 C4 C8 26.75(17) . . . . ?
C6 C3 C4 C8 146.55(12) . . . . ?
C2 C3 C4 C5 -98.37(13) . . . . ?
C6 C3 C4 C5 21.44(13) . . . . ?
C6 O2 C5 C9 162.44(12) . . . . ?
C6 O2 C5 C4 37.43(14) . . . . ?
C8 C4 C5 O2 -160.08(11) . . . . ?
C3 C4 C5 O2 -35.49(13) . . . . ?
C8 C4 C5 C9 80.88(15) . . . . ?
C3 C4 C5 C9 -154.54(12) . . . . ?
C5 O2 C6 O3 97.23(12) . . . . ?
C5 O2 C6 C3 -23.47(14) . . . . ?
C7 O3 C6 O2 -178.97(11) . . . . ?
C7 O3 C6 C3 -60.80(15) . . . . ?
C2 C3 C6 O2 121.63(12) . . . . ?
C4 C3 C6 O2 0.07(14) . . . . ?
C2 C3 C6 O3 4.01(16) . . . . ?
C4 C3 C6 O3 -117.54(12) . . . . ?
C6 O3 C7 C1 62.86(16) . . . . ?
O1 C1 C7 O3 172.84(14) . . . . ?
C2 C1 C7 O3 -7.08(18) . . . . ?
C5 C4 C8 O4 -6.1(2) . . . . ?
C3 C4 C8 O4 -124.80(16) . . . . ?
O2 C5 C9 C10 67.91(15) . . . . ?
C4 C5 C9 C10 -175.65(12) . . . . ?
C5 C9 C10 C11 176.27(12) . . . . ?
C9 C10 C11 C12 -172.77(12) . . . . ?
C10 C11 C12 C13 73.10(16) . . . . ?

# The following lines are used to test the character set of files sent by
# network email or other means. They are not part of the CIF data set
# abcdefghijklmnopqrstuvwxyzABCDEFGHIJKLMNOPQRSTUVWXYZ0123456789
# !@#$%^&*()_+{}:"~<>?|\-=[];'`,./

# END of CIF
####################################################################### 
# 
# 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_a20150171_diacetal2
_database_code_depnum_ccdc_archive 'CCDC 1525190'
_audit_update_record             
;
2017-01-02 deposited with the CCDC.
2017-01-30 downloaded from the CCDC.
;

_audit_creation_date             2016-07-26T17:03:33-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#


_chemical_name_systematic        
(2S,3S,3aS,7aR)-3-(1,3-dioxolan-2-yl)-2-phenyltetrahydro-4H,6H-spiro[furo[2,3-b]pyran-5,2'-[1,3]dioxolane]
_chemical_formula_moiety         'C18 H22 O6'
_chemical_formula_sum            'C18 H22 O6'
_chemical_formula_weight         334.37
_chemical_compound_source        'synthesis as described'
_chemical_absolute_configuration 2S,3S,3aS,7aR

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_space_group_crystal_system      orthorhombic
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           ' P 2ac 2ab'
_space_group_IT_number           19
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'

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'P 21 21 21'
_symmetry_Int_Tables_number      19
_cell_length_a                   8.96150(9)
_cell_length_b                   10.02283(10)
_cell_length_c                   17.71277(19)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1590.95(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    100.01(10)
_cell_measurement_reflns_used    19155
_cell_measurement_theta_min      4.975
_cell_measurement_theta_max      76.309

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.2389
_exptl_crystal_size_mid          0.1392
_exptl_crystal_size_min          0.053
_exptl_crystal_density_diffrn    1.3959
_exptl_crystal_F_000             714.5655
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 -5 6 0.035
5 2 1 0.0974
1 5 6 0.0656
-4 3 6 0.0814
-5 -3 -1 0.1129
1 -5 -7 0.0332
0 1 -1 0.0147
-3 -1 -10 0.0774

_exptl_special_details           
;
 ?
;

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    0.869
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   
;
        CrysAlisPro, Agilent Technologies,
        Version 1.171.36.24 (release 03-12-2012 CrysAlis171 .NET)
        (compiled Dec  3 2012,18:21:49)
Analytical numeric absorption correction using a multifaceted crystal
                        model based on expressions derived by R.C. Clark & J.S.
        (Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
;
_exptl_absorpt_correction_T_min  0.867
_exptl_absorpt_correction_T_max  0.962

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_ambient_temperature      100.15
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_monochromator  mirror
_diffrn_detector_area_resol_mean 5.2012
_diffrn_orient_matrix_ub_11      -0.0528922
_diffrn_orient_matrix_ub_12      -0.0498642
_diffrn_orient_matrix_ub_13      0.0778268
_diffrn_orient_matrix_ub_21      -0.1427712
_diffrn_orient_matrix_ub_22      0.0845443
_diffrn_orient_matrix_ub_23      -0.0075441
_diffrn_orient_matrix_ub_31      -0.0797732
_diffrn_orient_matrix_ub_32      -0.1182652
_diffrn_orient_matrix_ub_33      -0.0381326
_diffrn_measurement_device_type  'SuperNova, Single source at offset), Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_reflns_av_R_equivalents  0.0406
_diffrn_reflns_av_unetI/netI     0.053
_diffrn_reflns_number            31492
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         4.99
_diffrn_reflns_theta_max         72.44
_diffrn_reflns_theta_full        72.4372
_diffrn_measured_fraction_theta_full 0.9994
_diffrn_measured_fraction_theta_max 0.9994
_reflns_number_total             3160
_reflns_number_gt                3078
_reflns_threshold_expression     I>=2u(I)
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -67.00   -6.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.8256  125.0000 -180.0000 61

#__ type_ start__ end____ width___ exp.time_
  2 omega  -64.00   28.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.8256   57.0000  150.0000 92

#__ type_ start__ end____ width___ exp.time_
  3 omega  -42.00   -6.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      -83.0000   30.0000  -30.0000 36

#__ type_ start__ end____ width___ exp.time_
  4 omega  -67.00  -23.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      -83.0000   30.0000   30.0000 44

#__ type_ start__ end____ width___ exp.time_
  5 omega   44.00  109.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -94.0000  -90.0000 65

#__ type_ start__ end____ width___ exp.time_
  6 omega   36.00   68.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -30.0000  -30.0000 32

#__ type_ start__ end____ width___ exp.time_
  7 omega  101.00  146.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   61.0000  -30.0000 45

#__ type_ start__ end____ width___ exp.time_
  8 omega   35.00   61.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -30.0000    0.0000 26

#__ type_ start__ end____ width___ exp.time_
  9 omega   38.00   69.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -30.0000  -60.0000 31

#__ type_ start__ end____ width___ exp.time_
 10 omega   43.00   68.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -45.0000  150.0000 25

#__ type_ start__ end____ width___ exp.time_
 11 omega  101.00  149.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   45.0000  -90.0000 48

#__ type_ start__ end____ width___ exp.time_
 12 omega   86.00  122.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   61.0000    0.0000 36

#__ type_ start__ end____ width___ exp.time_
 13 omega   37.00   62.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -30.0000  120.0000 25

#__ type_ start__ end____ width___ exp.time_
 14 omega   58.00  145.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -77.0000   30.0000 87

#__ type_ start__ end____ width___ exp.time_
 15 omega -110.00  -11.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.8256  -57.0000    0.0000 99

#__ type_ start__ end____ width___ exp.time_
 16 omega -146.00  -95.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      -83.0000  178.0000  120.0000 51

#__ type_ start__ end____ width___ exp.time_
 17 omega  -51.00   -9.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      -83.0000   30.0000  -60.0000 42

#__ type_ start__ end____ width___ exp.time_
 18 omega   42.00   68.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -30.0000   90.0000 26

#__ type_ start__ end____ width___ exp.time_
 19 omega   87.00  156.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   45.0000  120.0000 69

#__ type_ start__ end____ width___ exp.time_
 20 omega   51.00   78.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000 -111.0000   60.0000 27

#__ type_ start__ end____ width___ exp.time_
 21 omega   47.00  108.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -94.0000  -30.0000 61

#__ type_ start__ end____ width___ exp.time_
 22 omega   37.00   64.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -30.0000  -90.0000 27

#__ type_ start__ end____ width___ exp.time_
 23 omega   58.00   98.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -94.0000 -150.0000 40

#__ type_ start__ end____ width___ exp.time_
 24 omega  111.00  155.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   45.0000 -150.0000 44

#__ type_ start__ end____ width___ exp.time_
 25 omega   39.00   65.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -30.0000 -120.0000 26

#__ type_ start__ end____ width___ exp.time_
 26 omega   69.00  110.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000 -111.0000 -180.0000 41

#__ type_ start__ end____ width___ exp.time_
 27 omega   43.00   77.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -45.0000 -180.0000 34

#__ type_ start__ end____ width___ exp.time_
 28 omega   83.00  116.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000 -111.0000   60.0000 33

#__ type_ start__ end____ width___ exp.time_
 29 omega   59.00   85.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000 -111.0000  -60.0000 26

#__ type_ start__ end____ width___ exp.time_
 30 omega   91.00  116.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000 -111.0000  -60.0000 25

#__ type_ start__ end____ width___ exp.time_
 31 omega  112.00  138.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   45.0000 -180.0000 26

#__ type_ start__ end____ width___ exp.time_
 32 omega   96.00  150.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  111.0000 -150.0000 54

#__ type_ start__ end____ width___ exp.time_
 33 omega -115.00  -11.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.8256  -57.0000   90.0000 104

#__ type_ start__ end____ width___ exp.time_
 34 omega -115.00  -11.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.8256  -57.0000  -90.0000 104

#__ type_ start__ end____ width___ exp.time_
 35 omega -115.00  -11.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.8256  -57.0000 -180.0000 104

#__ type_ start__ end____ width___ exp.time_
 36 omega    2.00   98.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       40.8256 -125.0000   60.0000 96

#__ type_ start__ end____ width___ exp.time_
 37 omega -162.00  -49.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      -83.0000  -77.0000  150.0000 113

#__ type_ start__ end____ width___ exp.time_
 38 omega -162.00  -49.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      -83.0000  -77.0000  -30.0000 113

#__ type_ start__ end____ width___ exp.time_
 39 omega -162.00  -49.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      -83.0000  -77.0000   90.0000 113

#__ type_ start__ end____ width___ exp.time_
 40 omega -162.00  -49.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      -83.0000  -77.0000  -90.0000 113

#__ type_ start__ end____ width___ exp.time_
 41 omega -162.00  -49.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      -83.0000  -77.0000   30.0000 113

#__ type_ start__ end____ width___ exp.time_
 42 omega -162.00  -49.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      -83.0000  -77.0000 -150.0000 113

#__ type_ start__ end____ width___ exp.time_
 43 omega   83.00  158.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   61.0000  150.0000 75

#__ type_ start__ end____ width___ exp.time_
 44 omega   83.00  158.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   61.0000  -60.0000 75

#__ type_ start__ end____ width___ exp.time_
 45 omega   35.00   69.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -30.0000 -120.0000 34

#__ type_ start__ end____ width___ exp.time_
 46 omega   29.00  109.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -94.0000 -180.0000 80

#__ type_ start__ end____ width___ exp.time_
 47 omega   35.00   69.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -30.0000   60.0000 34

#__ type_ start__ end____ width___ exp.time_
 48 omega   82.00  158.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   30.0000   60.0000 76

#__ type_ start__ end____ width___ exp.time_
 49 omega   35.00   69.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -30.0000  150.0000 34

#__ type_ start__ end____ width___ exp.time_
 50 omega   38.00   77.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -45.0000  -60.0000 39

#__ type_ start__ end____ width___ exp.time_
 51 omega   35.00   69.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -30.0000   30.0000 34

#__ type_ start__ end____ width___ exp.time_
 52 omega   79.00  158.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   77.0000   60.0000 79

#__ type_ start__ end____ width___ exp.time_
 53 omega   35.00   69.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -30.0000 -150.0000 34

#__ type_ start__ end____ width___ exp.time_
 54 omega   29.00   74.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -94.0000  -30.0000 45

#__ type_ start__ end____ width___ exp.time_
 55 omega   82.00  158.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   30.0000 -120.0000 76

;

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       
;
        CrysAlisPro, Agilent Technologies,
        Version 1.171.36.24 (release 03-12-2012 CrysAlis171 .NET)
        (compiled Dec  3 2012,18:21:49)
;
_computing_cell_refinement       
;
        CrysAlisPro, Agilent Technologies,
        Version 1.171.36.24 (release 03-12-2012 CrysAlis171 .NET)
        (compiled Dec  3 2012,18:21:49)
;
_computing_data_reduction        
;
        CrysAlisPro, Agilent Technologies,
        Version 1.171.36.24 (release 03-12-2012 CrysAlis171 .NET)
        (compiled Dec  3 2012,18:21:49)
;
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_computing_structure_refinement  'olex2.refine (Bourhis et al., 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION
#----------------------------------------------------------------------------#

_atom_sites_solution_primary     direct
_atom_sites_solution_hydrogens   geom

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0358P)²+0.2451P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    mixed
_refine_ls_number_reflns         3160
_refine_ls_number_parameters     216
_refine_ls_number_restraints     0
_refine_ls_number_constraints    38
_refine_ls_R_factor_all          0.0255
_refine_ls_R_factor_gt           0.0246
_refine_ls_wR_factor_ref         0.0638
_refine_ls_wR_factor_gt          0.0631
_refine_ls_goodness_of_fit_ref   1.0626
_refine_ls_restrained_S_all      1.0626
_refine_ls_shift/su_max          0.0002
_refine_ls_shift/su_mean         0.0001
_refine_ls_abs_structure_details 
'Flack, H. D. (1983). Acta Cryst. A39, 876-881.'
_refine_ls_abs_structure_Flack   0.06(11)
_refine_diff_density_max         0.157
_refine_diff_density_min         -0.1855
_refine_diff_density_rms         0.0345

#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
H 0 0 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
C 0.0192 0.00962 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
O 0.05239 0.03377 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'

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
O1 O -0.50877(10) -0.67508(8) -0.20842(5) 0.02256(18) Uani 1
O4 O -0.56698(9) -0.74653(8) -0.32613(4) 0.02022(18) Uani 1
O12 O -1.04148(9) -0.89282(8) -0.29398(4) 0.01972(18) Uani 1
O15 O -1.07564(10) -0.55423(9) -0.39832(5) 0.02297(19) Uani 1
O8 O -0.79853(9) -0.91918(8) -0.25884(5) 0.01885(17) Uani 1
O16 O -0.95047(10) -0.65309(8) -0.49449(4) 0.02027(17) Uani 1
C20 C -0.94026(14) -1.07502(11) -0.40417(6) 0.0204(2) Uani 1
H20 H -0.89833(14) -1.08260(11) -0.35510(6) 0.0245(3) Uiso 1
C5 C -0.67393(14) -0.86534(12) -0.21886(7) 0.0204(2) Uani 1
H5a H -0.70092(14) -0.85307(12) -0.16511(7) 0.0244(3) Uiso 1
H5b H -0.58946(14) -0.92885(12) -0.22135(7) 0.0244(3) Uiso 1
C17 C -1.01237(12) -0.95759(11) -0.42536(6) 0.0168(2) Uani 1
C11 C -0.90629(12) -0.73580(11) -0.36913(6) 0.0154(2) Uani 1
H11 H -0.80978(12) -0.77724(11) -0.38503(6) 0.0184(3) Uiso 1
C13 C -0.93815(13) -0.61553(11) -0.41798(6) 0.0174(2) Uani 1
H13 H -0.85541(13) -0.54933(11) -0.41230(6) 0.0209(3) Uiso 1
C21 C -1.07097(13) -0.94774(12) -0.49801(7) 0.0216(2) Uani 1
H21 H -1.12054(13) -0.86835(12) -0.51316(7) 0.0260(3) Uiso 1
C9 C -0.89888(12) -0.69988(11) -0.28456(6) 0.0160(2) Uani 1
H9 H -0.98516(12) -0.64048(11) -0.27222(6) 0.0192(3) Uiso 1
C22 C -0.92935(15) -1.18115(12) -0.45448(7) 0.0230(2) Uani 1
H22 H -0.88155(15) -1.26134(12) -0.43923(7) 0.0277(3) Uiso 1
C1BA C -0.75630(12) -0.63531(11) -0.25444(6) 0.0170(2) Uani 1
H1Ba H -0.73017(12) -0.55817(11) -0.28675(6) 0.0204(3) Uiso 1
H1Bb H -0.77495(12) -0.60142(11) -0.20280(6) 0.0204(3) Uiso 1
C24 C -0.98785(14) -1.17071(12) -0.52685(7) 0.0223(2) Uani 1
H24 H -0.98027(14) -1.24326(12) -0.56115(7) 0.0268(3) Uiso 1
C10 C -0.92773(13) -0.83637(11) -0.25047(7) 0.0180(2) Uani 1
H10 H -0.95799(13) -0.82899(11) -0.19629(7) 0.0216(3) Uiso 1
C2 C -0.62597(12) -0.73110(11) -0.25245(6) 0.0174(2) Uani 1
C14 C -1.03112(12) -0.84234(11) -0.37079(6) 0.0172(2) Uani 1
H14 H -1.12715(12) -0.79636(11) -0.38304(6) 0.0206(3) Uiso 1
C3 C -0.37152(13) -0.72513(13) -0.23921(8) 0.0249(3) Uani 1
H3a H -0.29408(13) -0.65469(13) -0.23960(8) 0.0299(3) Uiso 1
H3b H -0.33459(13) -0.80174(13) -0.20928(8) 0.0299(3) Uiso 1
C18 C -1.14375(15) -0.50894(14) -0.46709(7) 0.0262(3) Uani 1
H18a H -1.24029(15) -0.55446(14) -0.47573(7) 0.0314(3) Uiso 1
H18b H -1.16076(15) -0.41138(14) -0.46572(7) 0.0314(3) Uiso 1
C23 C -1.05742(14) -1.05327(13) -0.54848(7) 0.0237(2) Uani 1
H23 H -1.09614(14) -1.04481(13) -0.59817(7) 0.0285(3) Uiso 1
C7 C -0.40967(14) -0.76817(17) -0.31907(8) 0.0330(3) Uani 1
H7a H -0.38499(14) -0.86345(17) -0.32688(8) 0.0395(4) Uiso 1
H7b H -0.35409(14) -0.71406(17) -0.35643(8) 0.0395(4) Uiso 1
C19 C -1.03183(14) -0.54537(12) -0.52802(7) 0.0240(3) Uani 1
H19a H -0.96533(14) -0.46926(12) -0.53973(7) 0.0288(3) Uiso 1
H19b H -1.08275(14) -0.57430(12) -0.57484(7) 0.0288(3) Uiso 1



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

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 C2 1.4236(14) . ?
O1 C3 1.4359(15) . ?
O4 C2 1.4165(13) . ?
O4 C7 1.4317(14) . ?
O12 C10 1.3975(14) . ?
O12 C14 1.4546(13) . ?
O15 C13 1.4201(14) . ?
O15 C18 1.4361(14) . ?
O8 C5 1.4280(14) . ?
O8 C10 1.4323(14) . ?
O16 C13 1.4108(13) . ?
O16 C19 1.4318(14) . ?
C20 C17 1.3942(16) . ?
C20 C22 1.3911(16) . ?
C5 C2 1.5326(16) . ?
C17 C21 1.3933(16) . ?
C17 C14 1.5155(15) . ?
C11 C13 1.5111(15) . ?
C11 C9 1.5420(15) . ?
C11 C14 1.5468(15) . ?
C21 C23 1.3901(17) . ?
C9 C1BA 1.5284(15) . ?
C9 C10 1.5175(15) . ?
C22 C24 1.3889(18) . ?
C1BA C2 1.5124(15) . ?
C24 C23 1.3860(18) . ?
C3 C7 1.5179(19) . ?
C18 C19 1.5179(18) . ?

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
C3 O1 C2 106.62(9) . . ?
C7 O4 C2 107.67(9) . . ?
C14 O12 C10 109.18(8) . . ?
C18 O15 C13 107.31(9) . . ?
C10 O8 C5 111.21(8) . . ?
C19 O16 C13 103.72(8) . . ?
C22 C20 C17 120.37(11) . . ?
C2 C5 O8 111.01(9) . . ?
C21 C17 C20 118.89(10) . . ?
C14 C17 C20 121.54(10) . . ?
C14 C17 C21 119.55(10) . . ?
C9 C11 C13 112.22(9) . . ?
C14 C11 C13 113.78(9) . . ?
C14 C11 C9 102.17(8) . . ?
O16 C13 O15 106.44(9) . . ?
C11 C13 O15 111.63(9) . . ?
C11 C13 O16 110.61(9) . . ?
C23 C21 C17 120.47(11) . . ?
C1BA C9 C11 118.29(9) . . ?
C10 C9 C11 99.71(9) . . ?
C10 C9 C1BA 112.66(9) . . ?
C24 C22 C20 120.48(11) . . ?
C2 C1BA C9 112.64(9) . . ?
C23 C24 C22 119.26(11) . . ?
O8 C10 O12 107.34(9) . . ?
C9 C10 O12 105.65(9) . . ?
C9 C10 O8 110.09(9) . . ?
O4 C2 O1 105.81(9) . . ?
C5 C2 O1 109.91(9) . . ?
C5 C2 O4 111.50(9) . . ?
C1BA C2 O1 109.40(9) . . ?
C1BA C2 O4 109.63(9) . . ?
C1BA C2 C5 110.47(9) . . ?
C17 C14 O12 109.79(9) . . ?
C11 C14 O12 105.57(8) . . ?
C11 C14 C17 117.27(9) . . ?
C7 C3 O1 105.09(9) . . ?
C19 C18 O15 104.25(10) . . ?
C24 C23 C21 120.51(11) . . ?
C3 C7 O4 105.07(10) . . ?
C18 C19 O16 102.88(9) . . ?

# The following lines are used to test the character set of files sent by
# network email or other means. They are not part of the CIF data set
# abcdefghijklmnopqrstuvwxyzABCDEFGHIJKLMNOPQRSTUVWXYZ0123456789
# !@#$%^&*()_+{}:"~<>?|\-=[];'`,./

# END of CIF
