# Electronic Supplementary Material (ESI) for Green Chemistry.
# This journal is © The Royal Society of Chemistry 2016

####################################################################### 
# 
# 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_sts9
_database_code_depnum_ccdc_archive 'CCDC 1405838'
_audit_update_record             
;
2015-06-09 deposited with the CCDC.
2016-07-26 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            '8 in manuscript'
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C8 H8 O2'
_chemical_formula_weight         136.14

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_shelx_space_group_comment       
; 
The symmetry employed for this shelxl refinement is uniquely defined 
by the following loop, which should always be used as a source of 
symmetry information in preference to the above space-group names. 
They are only intended as comments. 
;

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

_cell_length_a                   6.6884(5)
_cell_length_b                   7.6318(6)
_cell_length_c                   12.9438(11)
_cell_angle_alpha                90
_cell_angle_beta                 100.414(2)
_cell_angle_gamma                90
_cell_volume                     649.83(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    200(2)
_cell_measurement_reflns_used    2192
_cell_measurement_theta_min      3.11
_cell_measurement_theta_max      27.19

_exptl_crystal_description       polyhedron
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.392
_exptl_crystal_F_000             288
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.110
_exptl_crystal_size_mid          0.090
_exptl_crystal_size_min          0.090
_exptl_absorpt_coefficient_mu    0.100
_shelx_estimated_absorpt_T_min   0.989
_shelx_estimated_absorpt_T_max   0.991
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.889748
_exptl_absorpt_correction_T_max  0.958936
_exptl_absorpt_process_details   
;
Sheldrick, G. M. (2008). SADABS. University of Göttingen, Germany.
;

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      200(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'ImuS microsource'
_diffrn_measurement_device_type  'Bruker APEX-II Quazar'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            6490
_diffrn_reflns_av_unetI/netI     0.0276
_diffrn_reflns_av_R_equivalents  0.0279
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         3.112
_diffrn_reflns_theta_max         27.386
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.930
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.930
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.930
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             1928
_reflns_number_gt                1534
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
; 
 _reflns_Friedel_fraction is defined as the number of unique 
 Friedel pairs measured divided by the number that would be 
 possible theoretically, ignoring centric projections and 
 systematic absences. 
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 Refined as a 2-component twin. 
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0585P)²+0.1766P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         1928
_refine_ls_number_parameters     96
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0551
_refine_ls_R_factor_gt           0.0421
_refine_ls_wR_factor_ref         0.1366
_refine_ls_wR_factor_gt          0.1313
_refine_ls_goodness_of_fit_ref   1.183
_refine_ls_restrained_S_all      1.183
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.5410(3) 0.1069(2) 0.90012(12) 0.0355(5) Uani 1 1 d . . . . .
H1 H 0.450(5) 0.158(4) 0.925(3) 0.059(10) Uiso 1 1 d . . . . .
C1 C 0.5312(3) 0.1489(3) 0.79653(17) 0.0256(5) Uani 1 1 d . . . . .
C2 C 0.6888(3) 0.0886(3) 0.74887(16) 0.0254(5) Uani 1 1 d . . . . .
H2 H 0.7953 0.0191 0.7867 0.030 Uiso 1 1 calc R U . . .
C3 C 0.6861(3) 0.1330(3) 0.64462(17) 0.0230(5) Uani 1 1 d . . . . .
C4 C 0.5293(4) 0.2307(3) 0.5880(2) 0.0230(6) Uani 1 1 d . . . . .
C5 C 0.3701(4) 0.2870(3) 0.63499(19) 0.0264(5) Uani 1 1 d . . . . .
H5 H 0.2607 0.3520 0.5960 0.032 Uiso 1 1 calc R U . . .
C6 C 0.3729(4) 0.2468(3) 0.7397(2) 0.0271(7) Uani 1 1 d . . . . .
H6 H 0.2658 0.2865 0.7731 0.033 Uiso 1 1 calc R U . . .
O7 O 0.7701(3) 0.1885(2) 0.48100(13) 0.0362(5) Uani 1 1 d . . . . .
C7 C 0.8373(4) 0.0911(3) 0.57600(17) 0.0302(6) Uani 1 1 d . . . . .
H7A H 0.9756 0.1280 0.6098 0.036 Uiso 1 1 calc R U . . .
H7B H 0.8387 -0.0361 0.5613 0.036 Uiso 1 1 calc R U . . .
C8 C 0.5695(5) 0.2584(3) 0.4787(2) 0.0303(6) Uani 1 1 d . . . . .
H8A H 0.4681 0.1954 0.4267 0.036 Uiso 1 1 calc R U . . .
H8B H 0.5648 0.3846 0.4607 0.036 Uiso 1 1 calc R U . . .


_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C1 1.369(3) . ?
O1 H1 0.83(4) . ?
C1 C6 1.392(3) . ?
C1 C2 1.392(3) . ?
C2 C3 1.388(3) . ?
C2 H2 0.9500 . ?
C3 C4 1.384(3) . ?
C3 C7 1.496(3) . ?
C4 C5 1.386(3) . ?
C4 C8 1.502(4) . ?
C5 C6 1.387(4) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
O7 C7 1.438(3) . ?
O7 C8 1.439(3) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 O1 H1 111(2) . . ?
O1 C1 C6 122.7(2) . . ?
O1 C1 C2 116.8(2) . . ?
C6 C1 C2 120.5(2) . . ?
C3 C2 C1 118.19(19) . . ?
C3 C2 H2 120.9 . . ?
C1 C2 H2 120.9 . . ?
C4 C3 C2 121.4(2) . . ?
C4 C3 C7 109.2(2) . . ?
C2 C3 C7 129.3(2) . . ?
C3 C4 C5 120.2(2) . . ?
C3 C4 C8 109.1(2) . . ?
C5 C4 C8 130.7(2) . . ?
C4 C5 C6 119.0(2) . . ?
C4 C5 H5 120.5 . . ?
C6 C5 H5 120.5 . . ?
C5 C6 C1 120.6(2) . . ?
C5 C6 H6 119.7 . . ?
C1 C6 H6 119.7 . . ?
C7 O7 C8 110.84(17) . . ?
O7 C7 C3 104.89(17) . . ?
O7 C7 H7A 110.8 . . ?
C3 C7 H7A 110.8 . . ?
O7 C7 H7B 110.8 . . ?
C3 C7 H7B 110.8 . . ?
H7A C7 H7B 108.8 . . ?
O7 C8 C4 104.7(2) . . ?
O7 C8 H8A 110.8 . . ?
C4 C8 H8A 110.8 . . ?
O7 C8 H8B 110.8 . . ?
C4 C8 H8B 110.8 . . ?
H8A C8 H8B 108.9 . . ?

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 -178.32(19) . . . . ?
C6 C1 C2 C3 1.7(3) . . . . ?
C1 C2 C3 C4 -1.5(3) . . . . ?
C1 C2 C3 C7 178.0(2) . . . . ?
C2 C3 C4 C5 0.0(3) . . . . ?
C7 C3 C4 C5 -179.56(19) . . . . ?
C2 C3 C4 C8 179.6(2) . . . . ?
C7 C3 C4 C8 0.0(2) . . . . ?
C3 C4 C5 C6 1.3(3) . . . . ?
C8 C4 C5 C6 -178.1(2) . . . . ?
C4 C5 C6 C1 -1.1(3) . . . . ?
O1 C1 C6 C5 179.6(2) . . . . ?
C2 C1 C6 C5 -0.4(3) . . . . ?
C8 O7 C7 C3 -11.2(2) . . . . ?
C4 C3 C7 O7 6.7(2) . . . . ?
C2 C3 C7 O7 -172.8(2) . . . . ?
C7 O7 C8 C4 11.2(2) . . . . ?
C3 C4 C8 O7 -6.7(2) . . . . ?
C5 C4 C8 O7 172.8(2) . . . . ?

_refine_diff_density_max         0.273
_refine_diff_density_min         -0.208
_refine_diff_density_rms         0.052

_shelxl_version_number           2014-3

####################################################################### 
# 
# 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_sts24
_database_code_depnum_ccdc_archive 'CCDC 1405839'
_audit_update_record             
;
2015-06-09 deposited with the CCDC.
2016-07-26 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            '9 in manuscript'
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C11 H14 O3'
_chemical_formula_weight         194.22

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_shelx_space_group_comment       
; 
The symmetry employed for this shelxl refinement is uniquely defined 
by the following loop, which should always be used as a source of 
symmetry information in preference to the above space-group names. 
They are only intended as comments. 
;

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

_cell_length_a                   4.5985(6)
_cell_length_b                   20.751(3)
_cell_length_c                   10.2612(13)
_cell_angle_alpha                90
_cell_angle_beta                 91.893(3)
_cell_angle_gamma                90
_cell_volume                     978.6(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    200(2)
_cell_measurement_reflns_used    3036
_cell_measurement_theta_min      2.79
_cell_measurement_theta_max      25.17

_exptl_crystal_description       keil
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.318
_exptl_crystal_F_000             416
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.410
_exptl_crystal_size_mid          0.090
_exptl_crystal_size_min          0.040
_exptl_absorpt_coefficient_mu    0.095
_shelx_estimated_absorpt_T_min   0.962
_shelx_estimated_absorpt_T_max   0.996
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7918
_exptl_absorpt_correction_T_max  0.9579
_exptl_absorpt_process_details   
;
Sheldrick, G. M. (2008). SADABS. University of Göttingen, Germany.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      200(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            6096
_diffrn_reflns_av_unetI/netI     0.0250
_diffrn_reflns_av_R_equivalents  0.0275
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         1.963
_diffrn_reflns_theta_max         25.179
_diffrn_reflns_theta_full        25.179
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 0.994
_reflns_number_total             1759
_reflns_number_gt                1484
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
; 
 Reflections were merged by SHELXL according to the crystal 
 class for the calculation of statistics and refinement. 
  
 _reflns_Friedel_fraction is defined as the number of unique 
 Friedel pairs measured divided by the number that would be 
 possible theoretically, ignoring centric projections and 
 systematic absences. 
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0508P)²+0.5307P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         1759
_refine_ls_number_parameters     129
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0498
_refine_ls_R_factor_gt           0.0417
_refine_ls_wR_factor_ref         0.1310
_refine_ls_wR_factor_gt          0.1264
_refine_ls_goodness_of_fit_ref   1.206
_refine_ls_restrained_S_all      1.206
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C11 C 0.3818(4) 0.68502(9) -0.03517(18) 0.0238(4) Uani 1 1 d . . . . .
O11 O 0.2995(3) 0.73737(7) 0.03490(13) 0.0321(4) Uani 1 1 d . . . . .
H11 H 0.1780 0.7260 0.0898 0.048 Uiso 1 1 calc R U . . .
C12 C 0.5736(4) 0.69656(9) -0.13531(17) 0.0229(4) Uani 1 1 d . . . . .
C13 C 0.6685(4) 0.64705(10) -0.21251(18) 0.0273(5) Uani 1 1 d . . . . .
C14 C 0.5760(5) 0.58415(10) -0.1940(2) 0.0352(5) Uani 1 1 d . . . . .
H14 H 0.6404 0.5500 -0.2476 0.042 Uiso 1 1 calc R U . . .
C15 C 0.3865(5) 0.57306(10) -0.0947(2) 0.0358(5) Uani 1 1 d . . . . .
H15 H 0.3218 0.5302 -0.0803 0.043 Uiso 1 1 calc R U . . .
C16 C 0.2862(4) 0.62198(10) -0.01454(19) 0.0297(5) Uani 1 1 d . . . . .
C17 C 0.7053(4) 0.75899(10) -0.17685(18) 0.0265(5) Uani 1 1 d . . . . .
H17A H 0.5529 0.7892 -0.2094 0.032 Uiso 1 1 calc R U . . .
H17B H 0.8154 0.7794 -0.1034 0.032 Uiso 1 1 calc R U . . .
O17 O 0.8963(3) 0.74150(7) -0.27941(15) 0.0368(4) Uani 1 1 d . . . . .
C18 C 0.8696(5) 0.67420(11) -0.31013(19) 0.0332(5) Uani 1 1 d . . . . .
H18A H 1.0618 0.6527 -0.3031 0.040 Uiso 1 1 calc R U . . .
H18B H 0.7881 0.6683 -0.3998 0.040 Uiso 1 1 calc R U . . .
C19 C 0.0830(5) 0.60591(12) 0.0924(2) 0.0393(6) Uani 1 1 d . . . . .
H19A H -0.0675 0.6398 0.0982 0.047 Uiso 1 1 calc R U . . .
H19B H -0.0156 0.5644 0.0732 0.047 Uiso 1 1 calc R U . . .
O20 O 0.2441(3) 0.60152(7) 0.21246(14) 0.0342(4) Uani 1 1 d . . . . .
C21 C 0.0672(5) 0.57980(10) 0.3150(2) 0.0350(5) Uani 1 1 d . . . . .
H21A H -0.0074 0.5360 0.2952 0.042 Uiso 1 1 calc R U . . .
H21B H -0.1011 0.6090 0.3239 0.042 Uiso 1 1 calc R U . . .
C22 C 0.2480(6) 0.57891(13) 0.4396(2) 0.0515(7) Uani 1 1 d . . . . .
H22A H 0.1312 0.5623 0.5103 0.077 Uiso 1 1 calc R U . . .
H22B H 0.3130 0.6228 0.4608 0.077 Uiso 1 1 calc R U . . .
H22C H 0.4178 0.5511 0.4290 0.077 Uiso 1 1 calc R U . . .


_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C11 O11 1.363(2) . ?
C11 C12 1.397(3) . ?
C11 C16 1.399(3) . ?
O11 H11 0.8400 . ?
C12 C13 1.377(3) . ?
C12 C17 1.498(3) . ?
C13 C14 1.388(3) . ?
C13 C18 1.496(3) . ?
C14 C15 1.382(3) . ?
C14 H14 0.9500 . ?
C15 C16 1.394(3) . ?
C15 H15 0.9500 . ?
C16 C19 1.502(3) . ?
C17 O17 1.440(2) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
O17 C18 1.436(3) . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C19 O20 1.420(3) . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
O20 C21 1.424(2) . ?
C21 C22 1.502(3) . ?
C21 H21A 0.9900 . ?
C21 H21B 0.9900 . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O11 C11 C12 116.39(17) . . ?
O11 C11 C16 124.84(17) . . ?
C12 C11 C16 118.76(18) . . ?
C11 O11 H11 109.5 . . ?
C13 C12 C11 120.99(18) . . ?
C13 C12 C17 110.06(17) . . ?
C11 C12 C17 128.95(17) . . ?
C12 C13 C14 121.26(19) . . ?
C12 C13 C18 108.58(18) . . ?
C14 C13 C18 130.16(19) . . ?
C15 C14 C13 117.4(2) . . ?
C15 C14 H14 121.3 . . ?
C13 C14 H14 121.3 . . ?
C14 C15 C16 122.9(2) . . ?
C14 C15 H15 118.6 . . ?
C16 C15 H15 118.6 . . ?
C15 C16 C11 118.69(19) . . ?
C15 C16 C19 119.7(2) . . ?
C11 C16 C19 121.6(2) . . ?
O17 C17 C12 104.61(15) . . ?
O17 C17 H17A 110.8 . . ?
C12 C17 H17A 110.8 . . ?
O17 C17 H17B 110.8 . . ?
C12 C17 H17B 110.8 . . ?
H17A C17 H17B 108.9 . . ?
C18 O17 C17 110.84(15) . . ?
O17 C18 C13 105.64(16) . . ?
O17 C18 H18A 110.6 . . ?
C13 C18 H18A 110.6 . . ?
O17 C18 H18B 110.6 . . ?
C13 C18 H18B 110.6 . . ?
H18A C18 H18B 108.7 . . ?
O20 C19 C16 109.20(16) . . ?
O20 C19 H19A 109.8 . . ?
C16 C19 H19A 109.8 . . ?
O20 C19 H19B 109.8 . . ?
C16 C19 H19B 109.8 . . ?
H19A C19 H19B 108.3 . . ?
C19 O20 C21 111.54(16) . . ?
O20 C21 C22 108.61(18) . . ?
O20 C21 H21A 110.0 . . ?
C22 C21 H21A 110.0 . . ?
O20 C21 H21B 110.0 . . ?
C22 C21 H21B 110.0 . . ?
H21A C21 H21B 108.3 . . ?
C21 C22 H22A 109.5 . . ?
C21 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C21 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 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
O11 C11 C12 C13 -179.51(16) . . . . ?
C16 C11 C12 C13 -0.2(3) . . . . ?
O11 C11 C12 C17 0.5(3) . . . . ?
C16 C11 C12 C17 179.79(18) . . . . ?
C11 C12 C13 C14 0.3(3) . . . . ?
C17 C12 C13 C14 -179.64(17) . . . . ?
C11 C12 C13 C18 179.96(16) . . . . ?
C17 C12 C13 C18 0.0(2) . . . . ?
C12 C13 C14 C15 -0.4(3) . . . . ?
C18 C13 C14 C15 -179.95(19) . . . . ?
C13 C14 C15 C16 0.3(3) . . . . ?
C14 C15 C16 C11 -0.2(3) . . . . ?
C14 C15 C16 C19 -179.33(19) . . . . ?
O11 C11 C16 C15 179.38(17) . . . . ?
C12 C11 C16 C15 0.1(3) . . . . ?
O11 C11 C16 C19 -1.5(3) . . . . ?
C12 C11 C16 C19 179.22(17) . . . . ?
C13 C12 C17 O17 -3.0(2) . . . . ?
C11 C12 C17 O17 176.98(17) . . . . ?
C12 C17 O17 C18 5.1(2) . . . . ?
C17 O17 C18 C13 -5.1(2) . . . . ?
C12 C13 C18 O17 3.1(2) . . . . ?
C14 C13 C18 O17 -177.33(19) . . . . ?
C15 C16 C19 O20 99.0(2) . . . . ?
C11 C16 C19 O20 -80.1(2) . . . . ?
C16 C19 O20 C21 -173.91(18) . . . . ?
C19 O20 C21 C22 -177.72(19) . . . . ?

_refine_diff_density_max         0.192
_refine_diff_density_min         -0.221
_refine_diff_density_rms         0.047

