# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2014

#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_11cis

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

_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C12 H16 O4'
_chemical_formula_sum            'C12 H16 O4'
_chemical_formula_weight         224.25
_chemical_compound_source        'synthesis as described'

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

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_Int_Tables_number      2
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   6.4719(5)
_cell_length_b                   8.7411(6)
_cell_length_c                   10.9321(8)
_cell_angle_alpha                110.196(4)
_cell_angle_beta                 95.635(4)
_cell_angle_gamma                101.286(4)
_cell_volume                     559.89(7)
_cell_formula_units_Z            2
_cell_measurement_temperature    193(2)
_cell_measurement_reflns_used    4870
_cell_measurement_theta_min      2.56
_cell_measurement_theta_max      31.07
_cell_measurement_wavelength     0.71073

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

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.12
_exptl_crystal_density_diffrn    1.33
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             240
_exptl_special_details           
;
 ?
;

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

_exptl_absorpt_coefficient_mu    0.099
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Bruker-AXS)'
_exptl_absorpt_correction_T_min  0.9766
_exptl_absorpt_correction_T_max  0.9882

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

_diffrn_ambient_temperature      193(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_radiation_probe          x-ray
_diffrn_reflns_av_R_equivalents  0.0203
_diffrn_reflns_av_unetI/netI     0.0206
_diffrn_reflns_number            10737
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.56
_diffrn_reflns_theta_max         28.28
_diffrn_reflns_theta_full        28.28
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.991
_reflns_number_total             2765
_reflns_number_gt                2198
_reflns_threshold_expression     >2sigma(I)

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

_computing_data_collection       'APEX2 (Bruker, 2006)'
_computing_cell_refinement       'APEX2 and SAINT (Bruker, 2006)'
_computing_data_reduction        'SAINT (Bruker, 2006)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_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 > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0483P)²+0.1860P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         2765
_refine_ls_number_parameters     148
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.051
_refine_ls_R_factor_gt           0.0379
_refine_ls_wR_factor_ref         0.1055
_refine_ls_wR_factor_gt          0.0961
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_restrained_S_all      1.036
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.372
_refine_diff_density_min         -0.201
_refine_diff_density_rms         0.042

#----------------------------------------------------------------------------#
#                   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 0.0033 0.0016 '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 0.0106 0.006 '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 0.38090(13) 0.08129(11) 0.15323(9) 0.0285(2) Uani 1 1 d . . .
H2 H 0.2896 -0.0112 0.1172 0.043 Uiso 1 1 calc R . .
O1 O -0.10520(15) 0.23706(11) -0.01853(9) 0.0284(2) Uani 1 1 d . . .
O3 O 0.27318(14) 0.18586(11) 0.35765(9) 0.0275(2) Uani 1 1 d . . .
O4 O 0.11931(14) 0.02434(11) 0.32983(9) 0.0279(2) Uani 1 1 d . . .
C5 C 0.28596(19) 0.20143(15) 0.23224(12) 0.0222(2) Uani 1 1 d . . .
C4 C 0.4348(2) 0.37554(15) 0.26458(13) 0.0258(3) Uani 1 1 d . . .
H4 H 0.5817 0.3834 0.3084 0.031 Uiso 1 1 calc R . .
C9 C -0.11029(19) 0.11601(15) 0.19771(12) 0.0217(2) Uani 1 1 d . . .
H9 H -0.2476 0.1084 0.1529 0.026 Uiso 1 1 calc R . .
C6 C 0.06376(18) 0.18761(14) 0.16359(11) 0.0195(2) Uani 1 1 d . . .
C8 C 0.4404(2) 0.40352(16) 0.13376(14) 0.0298(3) Uani 1 1 d . . .
H8A H 0.4554 0.3021 0.062 0.036 Uiso 1 1 calc R . .
H8B H 0.5584 0.5004 0.1435 0.036 Uiso 1 1 calc R . .
C1 C 0.2202(2) 0.43935(15) 0.10797(13) 0.0270(3) Uani 1 1 d . . .
H1 H 0.2115 0.4903 0.0392 0.032 Uiso 1 1 calc R . .
C10 C -0.09452(19) 0.04688(16) 0.30556(12) 0.0242(3) Uani 1 1 d . . .
C3 C 0.3423(2) 0.51902(16) 0.34785(13) 0.0317(3) Uani 1 1 d . . .
H3A H 0.459 0.6179 0.4037 0.038 Uiso 1 1 calc R . .
H3B H 0.2533 0.4821 0.4059 0.038 Uiso 1 1 calc R . .
C7 C 0.04597(19) 0.28011(14) 0.07242(12) 0.0214(2) Uani 1 1 d . . .
C2 C 0.2043(2) 0.56281(16) 0.24654(14) 0.0323(3) Uani 1 1 d . . .
H2A H 0.2604 0.6808 0.2558 0.039 Uiso 1 1 calc R . .
H2B H 0.0537 0.5473 0.26 0.039 Uiso 1 1 calc R . .
C12 C -0.1516(2) 0.16352(19) 0.43054(14) 0.0351(3) Uani 1 1 d . . .
H12A H -0.1427 0.1164 0.4997 0.053 Uiso 1 1 calc R . .
H12B H -0.2976 0.1747 0.4108 0.053 Uiso 1 1 calc R . .
H12C H -0.0511 0.2744 0.4614 0.053 Uiso 1 1 calc R . .
C11 C -0.2345(2) -0.13181(18) 0.26151(15) 0.0341(3) Uani 1 1 d . . .
H11A H -0.185 -0.2065 0.1868 0.051 Uiso 1 1 calc R . .
H11B H -0.3836 -0.1327 0.2341 0.051 Uiso 1 1 calc R . .
H11C H -0.2246 -0.1709 0.3353 0.051 Uiso 1 1 calc R . .



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

_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
O2 C5 1.3989(15) . ?
O2 H2 0.84 . ?
O1 C7 1.2222(15) . ?
O3 C5 1.4324(14) . ?
O3 O4 1.4735(12) . ?
O4 C10 1.4474(15) . ?
C5 C6 1.5177(16) . ?
C5 C4 1.5354(16) . ?
C4 C8 1.5344(18) . ?
C4 C3 1.5403(19) . ?
C4 H4 1 . ?
C9 C6 1.3295(16) . ?
C9 C10 1.5028(16) . ?
C9 H9 0.95 . ?
C6 C7 1.4935(16) . ?
C8 C1 1.5375(19) . ?
C8 H8A 0.99 . ?
C8 H8B 0.99 . ?
C1 C7 1.5121(16) . ?
C1 C2 1.5541(19) . ?
C1 H1 1 . ?
C10 C12 1.5254(19) . ?
C10 C11 1.5274(17) . ?
C3 C2 1.5501(19) . ?
C3 H3A 0.99 . ?
C3 H3B 0.99 . ?
C2 H2A 0.99 . ?
C2 H2B 0.99 . ?
C12 H12A 0.98 . ?
C12 H12B 0.98 . ?
C12 H12C 0.98 . ?
C11 H11A 0.98 . ?
C11 H11B 0.98 . ?
C11 H11C 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
C5 O2 H2 109.5 . . ?
C5 O3 O4 106.33(8) . . ?
C10 O4 O3 108.05(8) . . ?
O2 C5 O3 111.24(10) . . ?
O2 C5 C6 111.39(9) . . ?
O3 C5 C6 109.47(9) . . ?
O2 C5 C4 107.73(10) . . ?
O3 C5 C4 105.36(9) . . ?
C6 C5 C4 111.49(10) . . ?
C8 C4 C5 107.29(10) . . ?
C8 C4 C3 103.25(11) . . ?
C5 C4 C3 112.34(11) . . ?
C8 C4 H4 111.2 . . ?
C5 C4 H4 111.2 . . ?
C3 C4 H4 111.2 . . ?
C6 C9 C10 121.42(11) . . ?
C6 C9 H9 119.3 . . ?
C10 C9 H9 119.3 . . ?
C9 C6 C7 120.55(10) . . ?
C9 C6 C5 120.89(10) . . ?
C7 C6 C5 117.87(10) . . ?
C4 C8 C1 101.59(10) . . ?
C4 C8 H8A 111.5 . . ?
C1 C8 H8A 111.5 . . ?
C4 C8 H8B 111.5 . . ?
C1 C8 H8B 111.5 . . ?
H8A C8 H8B 109.3 . . ?
C7 C1 C8 109.67(10) . . ?
C7 C1 C2 108.05(10) . . ?
C8 C1 C2 102.45(10) . . ?
C7 C1 H1 112.1 . . ?
C8 C1 H1 112.1 . . ?
C2 C1 H1 112.1 . . ?
O4 C10 C9 109.14(9) . . ?
O4 C10 C12 111.70(10) . . ?
C9 C10 C12 110.22(10) . . ?
O4 C10 C11 102.70(10) . . ?
C9 C10 C11 111.81(10) . . ?
C12 C10 C11 111.08(11) . . ?
C4 C3 C2 105.66(11) . . ?
C4 C3 H3A 110.6 . . ?
C2 C3 H3A 110.6 . . ?
C4 C3 H3B 110.6 . . ?
C2 C3 H3B 110.6 . . ?
H3A C3 H3B 108.7 . . ?
O1 C7 C6 122.72(11) . . ?
O1 C7 C1 122.33(11) . . ?
C6 C7 C1 114.77(10) . . ?
C3 C2 C1 105.46(11) . . ?
C3 C2 H2A 110.6 . . ?
C1 C2 H2A 110.6 . . ?
C3 C2 H2B 110.6 . . ?
C1 C2 H2B 110.6 . . ?
H2A C2 H2B 108.8 . . ?
C10 C12 H12A 109.5 . . ?
C10 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C10 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?

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 O1 0.84 1.96 2.7941(12) 172.2 2

#===END
_database_code_depnum_ccdc_archive 'CCDC 997078'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_14cis

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

_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C12 H14 O4'
_chemical_formula_sum            'C12 H14 O4'
_chemical_formula_weight         222.23
_chemical_compound_source        'synthesis as described'

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

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/c'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_Int_Tables_number      14
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   6.5048(5)
_cell_length_b                   20.2812(16)
_cell_length_c                   8.3695(6)
_cell_angle_alpha                90
_cell_angle_beta                 99.728(4)
_cell_angle_gamma                90
_cell_volume                     1088.27(14)
_cell_formula_units_Z            4
_cell_measurement_temperature    193(2)
_cell_measurement_reflns_used    4299
_cell_measurement_theta_min      2.67
_cell_measurement_theta_max      26.01
_cell_measurement_wavelength     0.71073

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

_exptl_crystal_description       parallelepiped
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.04
_exptl_crystal_density_diffrn    1.356
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             472
_exptl_special_details           
;
 ?
;

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

_exptl_absorpt_coefficient_mu    0.102
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Bruker-AXS)'
_exptl_absorpt_correction_T_min  0.9780
_exptl_absorpt_correction_T_max  0.9959

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

_diffrn_ambient_temperature      193(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_radiation_probe          x-ray
_diffrn_reflns_av_R_equivalents  0.0371
_diffrn_reflns_av_unetI/netI     0.0271
_diffrn_reflns_number            17567
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         2.67
_diffrn_reflns_theta_max         26.88
_diffrn_reflns_theta_full        26.88
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_reflns_number_total             2338
_reflns_number_gt                1790
_reflns_threshold_expression     >2sigma(I)

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

_computing_data_collection       'APEX2 (Bruker, 2006)'
_computing_cell_refinement       'APEX2 and SAINT (Bruker, 2006)'
_computing_data_reduction        'SAINT (Bruker, 2006)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_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 > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0367P)²+0.3540P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         2338
_refine_ls_number_parameters     148
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.056
_refine_ls_R_factor_gt           0.0372
_refine_ls_wR_factor_ref         0.0908
_refine_ls_wR_factor_gt          0.0826
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_restrained_S_all      1.027
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.283
_refine_diff_density_min         -0.198
_refine_diff_density_rms         0.038

#----------------------------------------------------------------------------#
#                   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 0.0033 0.0016 '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 0.0106 0.006 '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
C1 C 0.2117(2) 0.43595(8) 0.88507(17) 0.0321(4) Uani 1 1 d . . .
H1 H 0.2183 0.4651 0.9822 0.038 Uiso 1 1 calc R . .
C2 C 0.1807(3) 0.36345(8) 0.92081(19) 0.0362(4) Uani 1 1 d . . .
H2 H 0.1036 0.3474 0.9995 0.043 Uiso 1 1 calc R . .
C3 C 0.2758(2) 0.32594(8) 0.82724(19) 0.0339(4) Uani 1 1 d . . .
H3 H 0.2752 0.2791 0.8272 0.041 Uiso 1 1 calc R . .
C4 C 0.3864(2) 0.36869(7) 0.71989(17) 0.0283(3) Uani 1 1 d . . .
H4 H 0.5214 0.349 0.7013 0.034 Uiso 1 1 calc R . .
C5 C 0.2411(2) 0.38559(7) 0.56044(17) 0.0237(3) Uani 1 1 d . . .
C6 C 0.0376(2) 0.41554(6) 0.59339(16) 0.0209(3) Uani 1 1 d . . .
C7 C 0.0398(2) 0.45477(7) 0.74575(16) 0.0246(3) Uani 1 1 d . . .
C8 C 0.4179(2) 0.43277(8) 0.81835(18) 0.0322(4) Uani 1 1 d . . .
H8A H 0.4344 0.4712 0.7487 0.039 Uiso 1 1 calc R . .
H8B H 0.5397 0.4299 0.9066 0.039 Uiso 1 1 calc R . .
C9 C -0.1423(2) 0.39858(7) 0.50252(16) 0.0232(3) Uani 1 1 d . . .
H9 H -0.2673 0.4188 0.5225 0.028 Uiso 1 1 calc R . .
C10 C -0.1538(2) 0.34845(7) 0.36917(17) 0.0267(3) Uani 1 1 d . . .
C11 C -0.2832(3) 0.37279(8) 0.21168(18) 0.0369(4) Uani 1 1 d . . .
H11A H -0.2185 0.4124 0.175 0.055 Uiso 1 1 calc R . .
H11B H -0.4246 0.3833 0.2297 0.055 Uiso 1 1 calc R . .
H11C H -0.2899 0.3383 0.1289 0.055 Uiso 1 1 calc R . .
C12 C -0.2358(3) 0.28318(8) 0.4243(2) 0.0393(4) Uani 1 1 d . . .
H12A H -0.2333 0.2498 0.34 0.059 Uiso 1 1 calc R . .
H12B H -0.3793 0.2891 0.4432 0.059 Uiso 1 1 calc R . .
H12C H -0.1475 0.2688 0.5248 0.059 Uiso 1 1 calc R . .
O1 O -0.09358(16) 0.49574(5) 0.75939(12) 0.0308(3) Uani 1 1 d . . .
O2 O 0.34954(15) 0.42813(5) 0.47308(12) 0.0295(3) Uani 1 1 d . . .
H2A H 0.2646 0.4479 0.4025 0.044 Uiso 1 1 calc R . .
O3 O 0.19727(15) 0.32441(5) 0.47743(12) 0.0292(3) Uani 1 1 d . . .
O4 O 0.05100(16) 0.33972(5) 0.32726(12) 0.0297(3) Uani 1 1 d . . .



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

_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 1.521(2) . ?
C1 C7 1.522(2) . ?
C1 C8 1.539(2) . ?
C1 H1 1 . ?
C2 C3 1.319(2) . ?
C2 H2 0.95 . ?
C3 C4 1.515(2) . ?
C3 H3 0.95 . ?
C4 C8 1.534(2) . ?
C4 C5 1.5381(19) . ?
C4 H4 1 . ?
C5 O2 1.3968(16) . ?
C5 O3 1.4271(17) . ?
C5 C6 1.5231(19) . ?
C6 C9 1.3290(19) . ?
C6 C7 1.5010(19) . ?
C7 O1 1.2206(17) . ?
C8 H8A 0.99 . ?
C8 H8B 0.99 . ?
C9 C10 1.5022(19) . ?
C9 H9 0.95 . ?
C10 O4 1.4448(17) . ?
C10 C11 1.521(2) . ?
C10 C12 1.527(2) . ?
C11 H11A 0.98 . ?
C11 H11B 0.98 . ?
C11 H11C 0.98 . ?
C12 H12A 0.98 . ?
C12 H12B 0.98 . ?
C12 H12C 0.98 . ?
O2 H2A 0.84 . ?
O3 O4 1.4756(14) . ?

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 C7 106.77(12) . . ?
C2 C1 C8 100.57(12) . . ?
C7 C1 C8 107.76(12) . . ?
C2 C1 H1 113.6 . . ?
C7 C1 H1 113.6 . . ?
C8 C1 H1 113.6 . . ?
C3 C2 C1 110.48(14) . . ?
C3 C2 H2 124.8 . . ?
C1 C2 H2 124.8 . . ?
C2 C3 C4 109.85(14) . . ?
C2 C3 H3 125.1 . . ?
C4 C3 H3 125.1 . . ?
C3 C4 C8 101.53(12) . . ?
C3 C4 C5 110.99(12) . . ?
C8 C4 C5 106.50(11) . . ?
C3 C4 H4 112.4 . . ?
C8 C4 H4 112.4 . . ?
C5 C4 H4 112.4 . . ?
O2 C5 O3 111.05(11) . . ?
O2 C5 C6 112.30(11) . . ?
O3 C5 C6 109.07(11) . . ?
O2 C5 C4 107.52(11) . . ?
O3 C5 C4 105.76(11) . . ?
C6 C5 C4 110.93(11) . . ?
C9 C6 C7 120.29(12) . . ?
C9 C6 C5 120.09(12) . . ?
C7 C6 C5 118.78(12) . . ?
O1 C7 C6 122.38(13) . . ?
O1 C7 C1 122.76(13) . . ?
C6 C7 C1 114.73(12) . . ?
C4 C8 C1 100.68(12) . . ?
C4 C8 H8A 111.6 . . ?
C1 C8 H8A 111.6 . . ?
C4 C8 H8B 111.6 . . ?
C1 C8 H8B 111.6 . . ?
H8A C8 H8B 109.4 . . ?
C6 C9 C10 121.93(13) . . ?
C6 C9 H9 119 . . ?
C10 C9 H9 119 . . ?
O4 C10 C9 109.33(11) . . ?
O4 C10 C11 103.14(11) . . ?
C9 C10 C11 112.01(12) . . ?
O4 C10 C12 110.52(12) . . ?
C9 C10 C12 109.79(12) . . ?
C11 C10 C12 111.87(13) . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C10 C12 H12A 109.5 . . ?
C10 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C10 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C5 O2 H2A 109.5 . . ?
C5 O3 O4 106.18(9) . . ?
C10 O4 O3 107.89(9) . . ?

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 H2A O1 0.84 1.97 2.8012(14) 172.1 3_566

#===END
_database_code_depnum_ccdc_archive 'CCDC 997079'
