# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2019

####################################################################### 
# 
# 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_cu_20160903A_0m_a_a
_database_code_depnum_ccdc_archive 'CCDC 1849055'
_audit_update_record             
;
2018-06-13 deposited with the CCDC.
2019-01-14 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        OK-23
_chemical_name_common            OK-23
_chemical_melting_point          ?
_chemical_formula_moiety         C12H10O4
_chemical_formula_sum            'C12 H10 O4'
_chemical_formula_weight         218.20

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_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, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   5.2763(4)
_cell_length_b                   13.5393(9)
_cell_length_c                   14.7358(7)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1052.69(12)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    3254
_cell_measurement_theta_min      8.871
_cell_measurement_theta_max      136.412

_exptl_crystal_description       acicular
_exptl_crystal_colour            white
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.377
_exptl_crystal_F_000             456
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_absorpt_coefficient_mu    0.874
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\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            9322
_diffrn_reflns_av_unetI/netI     0.1061
_diffrn_reflns_av_R_equivalents  0.1324
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         4.435
_diffrn_reflns_theta_max         68.319
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.974
_diffrn_measured_fraction_theta_full 0.975
_diffrn_reflns_Laue_measured_fraction_max 0.974
_diffrn_reflns_Laue_measured_fraction_full 0.975
_diffrn_reflns_point_group_measured_fraction_max 0.975
_diffrn_reflns_point_group_measured_fraction_full 0.975
_reflns_number_total             1883
_reflns_number_gt                1509
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.672
_reflns_Friedel_fraction_max     0.976
_reflns_Friedel_fraction_full    0.977

_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    'SHELXT 2014/5 (Sheldrick, 2014)'
_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)+(0.1492P)²] 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_abs_structure_details 
;
 Flack x determined using 512 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.0(3)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         1883
_refine_ls_number_parameters     149
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1121
_refine_ls_R_factor_gt           0.0915
_refine_ls_wR_factor_ref         0.2353
_refine_ls_wR_factor_gt          0.2209
_refine_ls_goodness_of_fit_ref   1.174
_refine_ls_restrained_S_all      1.174
_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
O001 O -0.2952(10) -0.5793(4) -0.5374(3) 0.0446(11) Uani 1 1 d . . . . .
H001 H -0.3724 -0.5483 -0.5764 0.067 Uiso 1 1 calc R U . . .
O002 O -0.9176(10) -0.4301(3) -0.3518(4) 0.0462(12) Uani 1 1 d . . . . .
H002 H -1.0048 -0.4440 -0.3075 0.069 Uiso 1 1 calc R U . . .
O003 O -0.7049(10) -0.6123(4) -0.1347(4) 0.0475(12) Uani 1 1 d . . . . .
O004 O -0.9726(10) -0.5031(4) -0.1891(4) 0.0500(13) Uani 1 1 d . . . . .
C005 C -0.7323(11) -0.4998(4) -0.3622(4) 0.0328(13) Uani 1 1 d . . . . .
C006 C -0.6639(11) -0.5654(4) -0.2919(4) 0.0315(12) Uani 1 1 d . . . . .
C007 C -0.3519(10) -0.6425(4) -0.3901(4) 0.0310(13) Uani 1 1 d . . . . .
C008 C -0.4760(11) -0.6369(4) -0.3077(4) 0.0295(12) Uani 1 1 d . . . . .
C009 C -0.4789(11) -0.6657(5) -0.1423(5) 0.0378(14) Uani 1 1 d . . . . .
C00A C -0.6088(13) -0.5036(4) -0.4437(4) 0.0370(14) Uani 1 1 d . . . . .
H00A H -0.6509 -0.4595 -0.4897 0.044 Uiso 1 1 calc R U . . .
C00B C -0.4213(11) -0.5732(4) -0.4575(4) 0.0325(12) Uani 1 1 d . . . . .
C00C C -0.7885(12) -0.5573(4) -0.2045(4) 0.0358(14) Uani 1 1 d . . . . .
C00D C -0.4336(11) -0.7118(4) -0.2331(4) 0.0347(13) Uani 1 1 d . . . . .
H00D H -0.2571 -0.7342 -0.2359 0.042 Uiso 1 1 calc R U . . .
C00E C -0.1549(13) -0.7187(5) -0.4122(5) 0.0448(15) Uani 1 1 d . . . . .
H00B H 0.0109 -0.6905 -0.4050 0.067 Uiso 1 1 calc R U . . .
H00C H -0.1763 -0.7403 -0.4738 0.067 Uiso 1 1 calc R U . . .
H00E H -0.1731 -0.7741 -0.3720 0.067 Uiso 1 1 calc R U . . .
C00F C -0.6084(14) -0.8020(5) -0.2476(6) 0.0482(17) Uani 1 1 d . . . . .
H00F H -0.7823 -0.7813 -0.2448 0.072 Uiso 1 1 calc R U . . .
H00G H -0.5768 -0.8501 -0.2011 0.072 Uiso 1 1 calc R U . . .
H00H H -0.5749 -0.8307 -0.3060 0.072 Uiso 1 1 calc R U . . .
C00G C -0.3391(16) -0.6768(6) -0.0681(6) 0.0549(19) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O001 C00B 1.355(8) . ?
O001 H001 0.8200 . ?
O002 C005 1.367(7) . ?
O002 H002 0.8200 . ?
O003 C00C 1.344(8) . ?
O003 C009 1.399(8) . ?
O004 C00C 1.238(8) . ?
C005 C00A 1.367(9) . ?
C005 C006 1.412(9) . ?
C006 C008 1.405(8) . ?
C006 C00C 1.450(9) . ?
C007 C008 1.382(9) . ?
C007 C00B 1.414(9) . ?
C007 C00E 1.501(8) . ?
C008 C00D 1.512(8) . ?
C009 C00G 1.327(11) . ?
C009 C00D 1.496(10) . ?
C00A C00B 1.382(9) . ?
C00A H00A 0.9300 . ?
C00D C00F 1.545(9) . ?
C00D H00D 0.9800 . ?
C00E H00B 0.9600 . ?
C00E H00C 0.9600 . ?
C00E H00E 0.9600 . ?
C00F H00F 0.9600 . ?
C00F H00G 0.9600 . ?
C00F H00H 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C00B O001 H001 109.5 . . ?
C005 O002 H002 109.5 . . ?
C00C O003 C009 120.3(5) . . ?
O002 C005 C00A 117.8(5) . . ?
O002 C005 C006 122.3(5) . . ?
C00A C005 C006 119.9(5) . . ?
C008 C006 C005 119.5(5) . . ?
C008 C006 C00C 121.3(5) . . ?
C005 C006 C00C 119.2(5) . . ?
C008 C007 C00B 117.3(5) . . ?
C008 C007 C00E 123.8(6) . . ?
C00B C007 C00E 118.8(6) . . ?
C007 C008 C006 121.2(5) . . ?
C007 C008 C00D 122.1(5) . . ?
C006 C008 C00D 116.5(5) . . ?
C00G C009 O003 117.8(7) . . ?
C00G C009 C00D 126.9(6) . . ?
O003 C009 C00D 115.0(5) . . ?
C005 C00A C00B 119.8(6) . . ?
C005 C00A H00A 120.1 . . ?
C00B C00A H00A 120.1 . . ?
O001 C00B C00A 121.4(5) . . ?
O001 C00B C007 116.3(5) . . ?
C00A C00B C007 122.3(6) . . ?
O004 C00C O003 116.4(6) . . ?
O004 C00C C006 124.3(6) . . ?
O003 C00C C006 119.2(5) . . ?
C009 C00D C008 110.2(5) . . ?
C009 C00D C00F 111.0(5) . . ?
C008 C00D C00F 110.0(5) . . ?
C009 C00D H00D 108.5 . . ?
C008 C00D H00D 108.5 . . ?
C00F C00D H00D 108.5 . . ?
C007 C00E H00B 109.5 . . ?
C007 C00E H00C 109.5 . . ?
H00B C00E H00C 109.5 . . ?
C007 C00E H00E 109.5 . . ?
H00B C00E H00E 109.5 . . ?
H00C C00E H00E 109.5 . . ?
C00D C00F H00F 109.5 . . ?
C00D C00F H00G 109.5 . . ?
H00F C00F H00G 109.5 . . ?
C00D C00F H00H 109.5 . . ?
H00F C00F H00H 109.5 . . ?
H00G C00F H00H 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
O002 C005 C006 C008 178.5(5) . . . . ?
C00A C005 C006 C008 -2.6(8) . . . . ?
O002 C005 C006 C00C -1.9(8) . . . . ?
C00A C005 C006 C00C 177.1(5) . . . . ?
C00B C007 C008 C006 0.2(8) . . . . ?
C00E C007 C008 C006 -178.2(5) . . . . ?
C00B C007 C008 C00D 174.9(5) . . . . ?
C00E C007 C008 C00D -3.5(8) . . . . ?
C005 C006 C008 C007 1.7(8) . . . . ?
C00C C006 C008 C007 -177.9(5) . . . . ?
C005 C006 C008 C00D -173.3(5) . . . . ?
C00C C006 C008 C00D 7.1(8) . . . . ?
C00C O003 C009 C00G 146.9(7) . . . . ?
C00C O003 C009 C00D -38.2(8) . . . . ?
O002 C005 C00A C00B -179.6(5) . . . . ?
C006 C005 C00A C00B 1.4(9) . . . . ?
C005 C00A C00B O001 179.9(6) . . . . ?
C005 C00A C00B C007 0.5(9) . . . . ?
C008 C007 C00B O001 179.3(5) . . . . ?
C00E C007 C00B O001 -2.3(8) . . . . ?
C008 C007 C00B C00A -1.3(8) . . . . ?
C00E C007 C00B C00A 177.1(6) . . . . ?
C009 O003 C00C O004 -171.7(6) . . . . ?
C009 O003 C00C C006 9.2(9) . . . . ?
C008 C006 C00C O004 -172.2(6) . . . . ?
C005 C006 C00C O004 8.1(9) . . . . ?
C008 C006 C00C O003 6.8(9) . . . . ?
C005 C006 C00C O003 -172.8(6) . . . . ?
C00G C009 C00D C008 -137.0(7) . . . . ?
O003 C009 C00D C008 48.7(7) . . . . ?
C00G C009 C00D C00F 100.9(8) . . . . ?
O003 C009 C00D C00F -73.5(6) . . . . ?
C007 C008 C00D C009 151.9(5) . . . . ?
C006 C008 C00D C009 -33.2(7) . . . . ?
C007 C008 C00D C00F -85.4(7) . . . . ?
C006 C008 C00D C00F 89.5(6) . . . . ?

_refine_diff_density_max         0.442
_refine_diff_density_min         -0.468
_refine_diff_density_rms         0.142


_exptl_crystal_recrystallization_method 'Vapour deposition'
_chemical_compound_source        fungus
####################################################################### 
# 
# 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_cu_20180706_0ma_b
_database_code_depnum_ccdc_archive 'CCDC 1855023'
_audit_update_record             
;
2018-07-10 deposited with the CCDC.
2019-01-14 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        OK-13
_chemical_name_common            OK-13
_chemical_melting_point          ?
_chemical_formula_moiety         C15H22O3
_chemical_formula_sum            'C15 H22 O3'
_chemical_formula_weight         250.32

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 21'
_space_group_name_Hall           'P 2yb'

_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'

_cell_length_a                   12.5559(4)
_cell_length_b                   10.0704(3)
_cell_length_c                   12.2295(4)
_cell_angle_alpha                90
_cell_angle_beta                 113.522(2)
_cell_angle_gamma                90
_cell_volume                     1417.84(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    8466
_cell_measurement_theta_min      7.679
_cell_measurement_theta_max      136.576

_exptl_crystal_description       acicular
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.173
_exptl_crystal_F_000             544
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_absorpt_coefficient_mu    0.642
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.3542
_exptl_absorpt_correction_T_max  0.7531
_exptl_absorpt_process_details   'SADABS 2014/5'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\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            15502
_diffrn_reflns_av_unetI/netI     0.0785
_diffrn_reflns_av_R_equivalents  0.0856
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_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         3.839
_diffrn_reflns_theta_max         66.574
_diffrn_reflns_theta_full        66.574
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_point_group_measured_fraction_full 0.988
_reflns_number_total             4927
_reflns_number_gt                4226
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.861
_reflns_Friedel_fraction_max     0.976
_reflns_Friedel_fraction_full    0.976

_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    'SHELXT 2014/5 (Sheldrick, 2014)'
_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)+(0.1110P)²] 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_abs_structure_details 
;
 Flack x determined using 1676 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.1(2)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         4927
_refine_ls_number_parameters     335
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0761
_refine_ls_R_factor_gt           0.0659
_refine_ls_wR_factor_ref         0.1746
_refine_ls_wR_factor_gt          0.1644
_refine_ls_goodness_of_fit_ref   1.068
_refine_ls_restrained_S_all      1.068
_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
O001 O 0.8322(3) 0.3577(3) 0.5657(3) 0.0254(6) Uani 1 1 d . . . . .
H001 H 0.7640 0.3343 0.5361 0.038 Uiso 1 1 calc R U . . .
O002 O -0.1942(3) 0.6829(4) 0.2421(3) 0.0377(8) Uani 1 1 d . . . . .
O003 O -0.1719(3) 0.6549(3) 0.0710(3) 0.0302(7) Uani 1 1 d . . . . .
H003 H -0.2425 0.6653 0.0416 0.045 Uiso 1 1 calc R U . . .
O004 O 1.6110(3) 0.7298(4) 0.9368(3) 0.0379(9) Uani 1 1 d . . . . .
O005 O 0.6161(3) 0.2728(4) 0.4426(3) 0.0323(7) Uani 1 1 d . . . . .
O006 O 0.7992(3) 0.3551(4) 0.7315(3) 0.0401(9) Uani 1 1 d . . . . .
C007 C 0.4017(4) 0.3626(4) 0.5553(3) 0.0208(8) Uani 1 1 d . . . . .
C008 C -0.1343(4) 0.6478(4) 0.1897(4) 0.0244(9) Uani 1 1 d . . . . .
C009 C -0.0152(4) 0.5967(4) 0.2427(4) 0.0221(8) Uani 1 1 d . . . . .
H009 H 0.0201 0.5787 0.1904 0.027 Uiso 1 1 calc R U . . .
C00A C 0.1689(4) 0.5188(4) 0.3944(4) 0.0257(9) Uani 1 1 d . . . . .
H00Q H 0.2237 0.5780 0.4523 0.031 Uiso 1 1 calc R U . . .
H00R H 0.1882 0.5153 0.3251 0.031 Uiso 1 1 calc R U . . .
C00B C 0.1995(4) 0.2264(6) 0.2416(4) 0.0341(11) Uani 1 1 d . . . . .
H00S H 0.1305 0.2767 0.2282 0.051 Uiso 1 1 calc R U . . .
H00U H 0.1895 0.1371 0.2634 0.051 Uiso 1 1 calc R U . . .
H00W H 0.2136 0.2252 0.1701 0.051 Uiso 1 1 calc R U . . .
C00C C 0.0482(4) 0.5730(4) 0.3582(4) 0.0215(8) Uani 1 1 d . . . . .
C00D C 0.5198(4) 0.2822(4) 0.4502(4) 0.0222(8) Uani 1 1 d . . . . .
C00E C 0.5049(4) 0.3509(4) 0.5465(4) 0.0224(8) Uani 1 1 d . . . . .
H00X H 0.5698 0.3892 0.6055 0.027 Uiso 1 1 calc R U . . .
C00F C 1.1819(4) 0.6385(4) 0.9587(4) 0.0248(9) Uani 1 1 d . . . . .
H00A H 1.1749 0.6288 1.0345 0.030 Uiso 1 1 calc R U . . .
H00B H 1.1190 0.6954 0.9086 0.030 Uiso 1 1 calc R U . . .
C00G C 1.3064(4) 0.7436(4) 0.8630(4) 0.0225(9) Uani 1 1 d . . . . .
C00H C 1.2989(4) 0.7081(4) 0.9808(3) 0.0223(9) Uani 1 1 d . . . . .
C00I C 0.2907(3) 0.3009(4) 0.4630(4) 0.0216(9) Uani 1 1 d . . . . .
C00J C 0.9856(4) 0.4256(4) 0.7396(4) 0.0238(9) Uani 1 1 d . . . . .
H00J H 1.0247 0.4397 0.6902 0.029 Uiso 1 1 calc R U . . .
C00K C 0.3957(4) 0.4293(5) 0.6629(4) 0.0276(9) Uani 1 1 d . . . . .
H00Y H 0.3636 0.5167 0.6416 0.041 Uiso 1 1 calc R U . . .
H H 0.4723 0.4356 0.7248 0.041 Uiso 1 1 calc R U . . .
HA H 0.3472 0.3780 0.6910 0.041 Uiso 1 1 calc R U . . .
C00L C 0.8648(4) 0.3765(4) 0.6827(4) 0.0243(9) Uani 1 1 d . . . . .
C00M C 1.3014(4) 0.8406(5) 1.0447(4) 0.0316(10) Uani 1 1 d . . . . .
H00C H 1.2372 0.8948 0.9957 0.047 Uiso 1 1 calc R U . . .
H00D H 1.3729 0.8861 1.0588 0.047 Uiso 1 1 calc R U . . .
H00E H 1.2958 0.8235 1.1194 0.047 Uiso 1 1 calc R U . . .
C00N C 0.1800(3) 0.3791(4) 0.4485(4) 0.0223(9) Uani 1 1 d . . . . .
H00Z H 0.1130 0.3274 0.3988 0.027 Uiso 1 1 calc R U . . .
HB H 0.1772 0.3872 0.5264 0.027 Uiso 1 1 calc R U . . .
C00O C 0.2796(4) 0.1624(4) 0.5132(4) 0.0284(10) Uani 1 1 d . . . . .
H00 H 0.2101 0.1196 0.4595 0.043 Uiso 1 1 calc R U . . .
HC H 0.2760 0.1729 0.5897 0.043 Uiso 1 1 calc R U . . .
HD H 0.3458 0.1091 0.5216 0.043 Uiso 1 1 calc R U . . .
C00P C 1.0433(4) 0.4514(4) 0.8547(4) 0.0249(9) Uani 1 1 d . . . . .
C00Q C 1.5183(4) 0.7166(5) 0.9492(4) 0.0250(9) Uani 1 1 d . . . . .
C00R C 0.4150(3) 0.2186(4) 0.3561(3) 0.0240(8) Uani 1 1 d . . . . .
H0AA H 0.4103 0.1265 0.3771 0.029 Uiso 1 1 calc R U . . .
HE H 0.4230 0.2201 0.2804 0.029 Uiso 1 1 calc R U . . .
C00S C 1.5180(4) 0.6737(5) 1.0661(4) 0.0287(10) Uani 1 1 d . . . . .
H00F H 1.5362 0.7493 1.1196 0.034 Uiso 1 1 calc R U . . .
H00G H 1.5782 0.6075 1.1015 0.034 Uiso 1 1 calc R U . . .
C00T C 1.4090(4) 0.7451(4) 0.8520(4) 0.0257(9) Uani 1 1 d . . . . .
H00T H 1.4093 0.7656 0.7780 0.031 Uiso 1 1 calc R U . . .
C00U C 1.1673(4) 0.5012(4) 0.8995(4) 0.0262(9) Uani 1 1 d . . . . .
H00H H 1.1909 0.5063 0.8332 0.031 Uiso 1 1 calc R U . . .
H00I H 1.2180 0.4383 0.9568 0.031 Uiso 1 1 calc R U . . .
C00V C 1.4014(4) 0.6157(4) 1.0535(4) 0.0241(9) Uani 1 1 d . . . . .
H00V H 1.3908 0.5332 1.0078 0.029 Uiso 1 1 calc R U . . .
C00W C 0.3033(3) 0.2905(4) 0.3427(4) 0.0214(8) Uani 1 1 d . . . . .
H1AA H 0.3097 0.3815 0.3174 0.026 Uiso 1 1 calc R U . . .
C00X C 0.9966(4) 0.4328(6) 0.9490(4) 0.0352(11) Uani 1 1 d . . . . .
H00K H 0.9647 0.5151 0.9617 0.053 Uiso 1 1 calc R U . . .
H00L H 1.0582 0.4051 1.0220 0.053 Uiso 1 1 calc R U . . .
H00M H 0.9369 0.3662 0.9236 0.053 Uiso 1 1 calc R U . . .
C00Y C 0.0067(4) 0.5951(5) 0.4557(4) 0.0328(10) Uani 1 1 d . . . . .
H2AA H -0.0368 0.6764 0.4413 0.049 Uiso 1 1 calc R U . . .
HF H 0.0723 0.6008 0.5309 0.049 Uiso 1 1 calc R U . . .
HG H -0.0420 0.5225 0.4576 0.049 Uiso 1 1 calc R U . . .
C00Z C 1.4058(4) 0.5773(6) 1.1758(4) 0.0411(12) Uani 1 1 d . . . . .
H00N H 1.3373 0.5280 1.1663 0.062 Uiso 1 1 calc R U . . .
H00O H 1.4096 0.6562 1.2213 0.062 Uiso 1 1 calc R U . . .
H00P H 1.4733 0.5237 1.2167 0.062 Uiso 1 1 calc R U . . .
C010 C 1.1990(4) 0.7881(5) 0.7598(4) 0.0334(10) Uani 1 1 d . . . . .
H01A H 1.2199 0.8223 0.6978 0.050 Uiso 1 1 calc R U . . .
H01B H 1.1610 0.8563 0.7859 0.050 Uiso 1 1 calc R U . . .
H01C H 1.1473 0.7141 0.7298 0.050 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
O001 C00L 1.335(5) . ?
O001 H001 0.8200 . ?
O002 C008 1.218(6) . ?
O003 C008 1.338(5) . ?
O003 H003 0.8200 . ?
O004 C00Q 1.241(5) . ?
O005 C00D 1.253(5) . ?
O006 C00L 1.214(6) . ?
C007 C00E 1.348(6) . ?
C007 C00K 1.506(6) . ?
C007 C00I 1.532(6) . ?
C008 C009 1.466(6) . ?
C009 C00C 1.337(6) . ?
C009 H009 0.9300 . ?
C00A C00C 1.501(6) . ?
C00A C00N 1.538(5) . ?
C00A H00Q 0.9700 . ?
C00A H00R 0.9700 . ?
C00B C00W 1.535(6) . ?
C00B H00S 0.9600 . ?
C00B H00U 0.9600 . ?
C00B H00W 0.9600 . ?
C00C C00Y 1.497(6) . ?
C00D C00E 1.441(6) . ?
C00D C00R 1.503(6) . ?
C00E H00X 0.9300 . ?
C00F C00U 1.537(6) . ?
C00F C00H 1.550(6) . ?
C00F H00A 0.9700 . ?
C00F H00B 0.9700 . ?
C00G C00T 1.347(6) . ?
C00G C010 1.501(6) . ?
C00G C00H 1.524(5) . ?
C00H C00M 1.540(6) . ?
C00H C00V 1.549(6) . ?
C00I C00W 1.544(5) . ?
C00I C00N 1.545(6) . ?
C00I C00O 1.553(5) . ?
C00J C00P 1.326(6) . ?
C00J C00L 1.479(6) . ?
C00J H00J 0.9300 . ?
C00K H00Y 0.9600 . ?
C00K H 0.9600 . ?
C00K HA 0.9600 . ?
C00M H00C 0.9600 . ?
C00M H00D 0.9600 . ?
C00M H00E 0.9600 . ?
C00N H00Z 0.9700 . ?
C00N HB 0.9700 . ?
C00O H00 0.9600 . ?
C00O HC 0.9600 . ?
C00O HD 0.9600 . ?
C00P C00X 1.499(6) . ?
C00P C00U 1.516(6) . ?
C00Q C00T 1.441(6) . ?
C00Q C00S 1.495(6) . ?
C00R C00W 1.528(6) . ?
C00R H0AA 0.9700 . ?
C00R HE 0.9700 . ?
C00S C00V 1.526(6) . ?
C00S H00F 0.9700 . ?
C00S H00G 0.9700 . ?
C00T H00T 0.9300 . ?
C00U H00H 0.9700 . ?
C00U H00I 0.9700 . ?
C00V C00Z 1.523(6) . ?
C00V H00V 0.9800 . ?
C00W H1AA 0.9800 . ?
C00X H00K 0.9600 . ?
C00X H00L 0.9600 . ?
C00X H00M 0.9600 . ?
C00Y H2AA 0.9600 . ?
C00Y HF 0.9600 . ?
C00Y HG 0.9600 . ?
C00Z H00N 0.9600 . ?
C00Z H00O 0.9600 . ?
C00Z H00P 0.9600 . ?
C010 H01A 0.9600 . ?
C010 H01B 0.9600 . ?
C010 H01C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C00L O001 H001 109.5 . . ?
C008 O003 H003 109.5 . . ?
C00E C007 C00K 119.6(4) . . ?
C00E C007 C00I 121.8(4) . . ?
C00K C007 C00I 118.4(4) . . ?
O002 C008 O003 122.1(4) . . ?
O002 C008 C009 127.1(4) . . ?
O003 C008 C009 110.7(4) . . ?
C00C C009 C008 127.0(4) . . ?
C00C C009 H009 116.5 . . ?
C008 C009 H009 116.5 . . ?
C00C C00A C00N 111.6(4) . . ?
C00C C00A H00Q 109.3 . . ?
C00N C00A H00Q 109.3 . . ?
C00C C00A H00R 109.3 . . ?
C00N C00A H00R 109.3 . . ?
H00Q C00A H00R 108.0 . . ?
C00W C00B H00S 109.5 . . ?
C00W C00B H00U 109.5 . . ?
H00S C00B H00U 109.5 . . ?
C00W C00B H00W 109.5 . . ?
H00S C00B H00W 109.5 . . ?
H00U C00B H00W 109.5 . . ?
C009 C00C C00Y 124.4(4) . . ?
C009 C00C C00A 118.8(4) . . ?
C00Y C00C C00A 116.8(4) . . ?
O005 C00D C00E 122.8(4) . . ?
O005 C00D C00R 119.2(4) . . ?
C00E C00D C00R 118.1(4) . . ?
C007 C00E C00D 123.4(4) . . ?
C007 C00E H00X 118.3 . . ?
C00D C00E H00X 118.3 . . ?
C00U C00F C00H 114.5(3) . . ?
C00U C00F H00A 108.6 . . ?
C00H C00F H00A 108.6 . . ?
C00U C00F H00B 108.6 . . ?
C00H C00F H00B 108.6 . . ?
H00A C00F H00B 107.6 . . ?
C00T C00G C010 119.2(4) . . ?
C00T C00G C00H 121.3(4) . . ?
C010 C00G C00H 119.4(4) . . ?
C00G C00H C00M 106.2(4) . . ?
C00G C00H C00V 109.4(3) . . ?
C00M C00H C00V 112.6(4) . . ?
C00G C00H C00F 110.7(3) . . ?
C00M C00H C00F 107.9(3) . . ?
C00V C00H C00F 109.9(3) . . ?
C007 C00I C00W 108.7(3) . . ?
C007 C00I C00N 113.0(4) . . ?
C00W C00I C00N 110.8(3) . . ?
C007 C00I C00O 105.8(3) . . ?
C00W C00I C00O 112.0(4) . . ?
C00N C00I C00O 106.5(3) . . ?
C00P C00J C00L 126.0(4) . . ?
C00P C00J H00J 117.0 . . ?
C00L C00J H00J 117.0 . . ?
C007 C00K H00Y 109.5 . . ?
C007 C00K H 109.5 . . ?
H00Y C00K H 109.5 . . ?
C007 C00K HA 109.5 . . ?
H00Y C00K HA 109.5 . . ?
H C00K HA 109.5 . . ?
O006 C00L O001 121.6(4) . . ?
O006 C00L C00J 126.7(4) . . ?
O001 C00L C00J 111.7(4) . . ?
C00H C00M H00C 109.5 . . ?
C00H C00M H00D 109.5 . . ?
H00C C00M H00D 109.5 . . ?
C00H C00M H00E 109.5 . . ?
H00C C00M H00E 109.5 . . ?
H00D C00M H00E 109.5 . . ?
C00A C00N C00I 116.1(3) . . ?
C00A C00N H00Z 108.3 . . ?
C00I C00N H00Z 108.3 . . ?
C00A C00N HB 108.3 . . ?
C00I C00N HB 108.3 . . ?
H00Z C00N HB 107.4 . . ?
C00I C00O H00 109.5 . . ?
C00I C00O HC 109.5 . . ?
H00 C00O HC 109.5 . . ?
C00I C00O HD 109.5 . . ?
H00 C00O HD 109.5 . . ?
HC C00O HD 109.5 . . ?
C00J C00P C00X 125.2(4) . . ?
C00J C00P C00U 119.7(4) . . ?
C00X C00P C00U 115.1(4) . . ?
O004 C00Q C00T 120.6(4) . . ?
O004 C00Q C00S 120.6(4) . . ?
C00T C00Q C00S 118.8(4) . . ?
C00D C00R C00W 111.5(3) . . ?
C00D C00R H0AA 109.3 . . ?
C00W C00R H0AA 109.3 . . ?
C00D C00R HE 109.3 . . ?
C00W C00R HE 109.3 . . ?
H0AA C00R HE 108.0 . . ?
C00Q C00S C00V 112.5(3) . . ?
C00Q C00S H00F 109.1 . . ?
C00V C00S H00F 109.1 . . ?
C00Q C00S H00G 109.1 . . ?
C00V C00S H00G 109.1 . . ?
H00F C00S H00G 107.8 . . ?
C00G C00T C00Q 123.3(4) . . ?
C00G C00T H00T 118.4 . . ?
C00Q C00T H00T 118.4 . . ?
C00P C00U C00F 112.4(4) . . ?
C00P C00U H00H 109.1 . . ?
C00F C00U H00H 109.1 . . ?
C00P C00U H00I 109.1 . . ?
C00F C00U H00I 109.1 . . ?
H00H C00U H00I 107.9 . . ?
C00Z C00V C00S 109.9(4) . . ?
C00Z C00V C00H 114.3(4) . . ?
C00S C00V C00H 111.9(4) . . ?
C00Z C00V H00V 106.8 . . ?
C00S C00V H00V 106.8 . . ?
C00H C00V H00V 106.8 . . ?
C00R C00W C00B 109.5(4) . . ?
C00R C00W C00I 111.6(3) . . ?
C00B C00W C00I 114.8(3) . . ?
C00R C00W H1AA 106.8 . . ?
C00B C00W H1AA 106.8 . . ?
C00I C00W H1AA 106.8 . . ?
C00P C00X H00K 109.5 . . ?
C00P C00X H00L 109.5 . . ?
H00K C00X H00L 109.5 . . ?
C00P C00X H00M 109.5 . . ?
H00K C00X H00M 109.5 . . ?
H00L C00X H00M 109.5 . . ?
C00C C00Y H2AA 109.5 . . ?
C00C C00Y HF 109.5 . . ?
H2AA C00Y HF 109.5 . . ?
C00C C00Y HG 109.5 . . ?
H2AA C00Y HG 109.5 . . ?
HF C00Y HG 109.5 . . ?
C00V C00Z H00N 109.5 . . ?
C00V C00Z H00O 109.5 . . ?
H00N C00Z H00O 109.5 . . ?
C00V C00Z H00P 109.5 . . ?
H00N C00Z H00P 109.5 . . ?
H00O C00Z H00P 109.5 . . ?
C00G C010 H01A 109.5 . . ?
C00G C010 H01B 109.5 . . ?
H01A C010 H01B 109.5 . . ?
C00G C010 H01C 109.5 . . ?
H01A C010 H01C 109.5 . . ?
H01B C010 H01C 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
O002 C008 C009 C00C 3.4(8) . . . . ?
O003 C008 C009 C00C -177.9(4) . . . . ?
C008 C009 C00C C00Y 0.2(7) . . . . ?
C008 C009 C00C C00A 179.3(4) . . . . ?
C00N C00A C00C C009 -115.8(4) . . . . ?
C00N C00A C00C C00Y 63.4(5) . . . . ?
C00K C007 C00E C00D 176.4(4) . . . . ?
C00I C007 C00E C00D 0.9(6) . . . . ?
O005 C00D C00E C007 179.5(4) . . . . ?
C00R C00D C00E C007 -1.0(6) . . . . ?
C00T C00G C00H C00M 94.8(5) . . . . ?
C010 C00G C00H C00M -80.4(5) . . . . ?
C00T C00G C00H C00V -27.1(5) . . . . ?
C010 C00G C00H C00V 157.7(4) . . . . ?
C00T C00G C00H C00F -148.4(4) . . . . ?
C010 C00G C00H C00F 36.4(5) . . . . ?
C00U C00F C00H C00G 66.5(5) . . . . ?
C00U C00F C00H C00M -177.7(4) . . . . ?
C00U C00F C00H C00V -54.5(5) . . . . ?
C00E C007 C00I C00W -26.9(5) . . . . ?
C00K C007 C00I C00W 157.6(4) . . . . ?
C00E C007 C00I C00N -150.3(4) . . . . ?
C00K C007 C00I C00N 34.2(5) . . . . ?
C00E C007 C00I C00O 93.6(4) . . . . ?
C00K C007 C00I C00O -81.9(5) . . . . ?
C00P C00J C00L O006 1.8(8) . . . . ?
C00P C00J C00L O001 -178.8(4) . . . . ?
C00C C00A C00N C00I 166.8(3) . . . . ?
C007 C00I C00N C00A 66.9(5) . . . . ?
C00W C00I C00N C00A -55.4(5) . . . . ?
C00O C00I C00N C00A -177.4(4) . . . . ?
C00L C00J C00P C00X 1.2(8) . . . . ?
C00L C00J C00P C00U 179.9(4) . . . . ?
O005 C00D C00R C00W -152.5(4) . . . . ?
C00E C00D C00R C00W 27.9(5) . . . . ?
O004 C00Q C00S C00V -159.3(5) . . . . ?
C00T C00Q C00S C00V 22.0(6) . . . . ?
C010 C00G C00T C00Q 173.9(4) . . . . ?
C00H C00G C00T C00Q -1.3(7) . . . . ?
O004 C00Q C00T C00G -174.2(5) . . . . ?
C00S C00Q C00T C00G 4.6(7) . . . . ?
C00J C00P C00U C00F 119.8(5) . . . . ?
C00X C00P C00U C00F -61.4(5) . . . . ?
C00H C00F C00U C00P -167.1(4) . . . . ?
C00Q C00S C00V C00Z -178.5(4) . . . . ?
C00Q C00S C00V C00H -50.4(5) . . . . ?
C00G C00H C00V C00Z 177.8(4) . . . . ?
C00M C00H C00V C00Z 59.9(5) . . . . ?
C00F C00H C00V C00Z -60.4(5) . . . . ?
C00G C00H C00V C00S 52.1(4) . . . . ?
C00M C00H C00V C00S -65.8(5) . . . . ?
C00F C00H C00V C00S 173.9(3) . . . . ?
C00D C00R C00W C00B 177.2(4) . . . . ?
C00D C00R C00W C00I -54.5(5) . . . . ?
C007 C00I C00W C00R 52.9(4) . . . . ?
C00N C00I C00W C00R 177.6(3) . . . . ?
C00O C00I C00W C00R -63.6(4) . . . . ?
C007 C00I C00W C00B 178.3(4) . . . . ?
C00N C00I C00W C00B -57.0(5) . . . . ?
C00O C00I C00W C00B 61.8(5) . . . . ?

_refine_diff_density_max         0.275
_refine_diff_density_min         -0.404
_refine_diff_density_rms         0.089

####################################################################### 
# 
# 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_cu_20180710_0m_a
_database_code_depnum_ccdc_archive 'CCDC 1855706'
_audit_update_record             
;
2018-07-13 deposited with the CCDC.
2019-01-14 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        OK-21
_chemical_name_common            OK-21
_chemical_melting_point          ?
_chemical_formula_moiety         C16H20O4
_chemical_formula_sum            'C16 H20 O4'
_chemical_formula_weight         276.32

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           1
_space_group_name_H-M_alt        'P 1'
_space_group_name_Hall           'P 1'

_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'

_cell_length_a                   8.9882(3)
_cell_length_b                   9.3953(3)
_cell_length_c                   10.2162(4)
_cell_angle_alpha                69.449(2)
_cell_angle_beta                 70.162(2)
_cell_angle_gamma                66.207(2)
_cell_volume                     719.21(5)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    4090
_cell_measurement_theta_min      4.75
_cell_measurement_theta_max      72.23

_exptl_crystal_description       acicular
_exptl_crystal_colour            white
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.276
_exptl_crystal_F_000             296
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_absorpt_coefficient_mu    0.742
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\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            14119
_diffrn_reflns_av_unetI/netI     0.1084
_diffrn_reflns_av_R_equivalents  0.1069
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         4.751
_diffrn_reflns_theta_max         66.577
_diffrn_reflns_theta_full        66.577
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.958
_diffrn_reflns_point_group_measured_fraction_full 0.958
_reflns_number_total             4860
_reflns_number_gt                3526
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.918
_reflns_Friedel_fraction_max     0.917
_reflns_Friedel_fraction_full    0.917

_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    'SHELXT 2014/5 (Sheldrick, 2014)'

_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)+(0.0716P)²] 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_abs_structure_details 
;
 Flack x determined using 1145 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.2(4)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         4860
_refine_ls_number_parameters     371
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0891
_refine_ls_R_factor_gt           0.0603
_refine_ls_wR_factor_ref         0.1583
_refine_ls_wR_factor_gt          0.1427
_refine_ls_goodness_of_fit_ref   1.018
_refine_ls_restrained_S_all      1.017
_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
O001 O 0.9302(6) 0.0080(5) 0.3088(5) 0.0237(10) Uani 1 1 d . . . . .
O002 O 0.3940(5) 0.7596(6) 0.2324(5) 0.0253(10) Uani 1 1 d . . . . .
O003 O 0.1038(5) 0.9950(5) 0.7139(5) 0.0227(10) Uani 1 1 d . . . . .
O004 O 0.6538(5) 0.2496(6) 0.7845(5) 0.0246(10) Uani 1 1 d . . . . .
O005 O 0.2853(6) 0.6206(6) 0.5293(5) 0.0299(11) Uani 1 1 d . . . . .
O006 O 0.7636(7) 0.3830(6) 0.4912(5) 0.0354(12) Uani 1 1 d . . . . .
O007 O 0.5063(7) 0.5027(7) 0.7986(8) 0.0539(17) Uani 1 1 d . . . . .
C008 C 0.4518(8) 1.0374(9) 0.3230(7) 0.0242(15) Uani 1 1 d . . . . .
C009 C 0.8186(8) 0.0050(8) 0.4373(7) 0.0210(14) Uani 1 1 d . . . . .
O00A O 0.5585(7) 0.5119(8) 0.2082(8) 0.0526(16) Uani 1 1 d . . . . .
C00B C 0.8131(8) 0.2682(8) 0.4411(7) 0.0213(13) Uani 1 1 d . . . . .
C00C C 0.5737(8) 1.0674(10) 0.1805(8) 0.0329(16) Uani 1 1 d . . . . .
H00L H 0.5688 1.1778 0.1513 0.049 Uiso 1 1 calc R U . . .
H00M H 0.5452 1.0441 0.1096 0.049 Uiso 1 1 calc R U . . .
H00N H 0.6848 0.9994 0.1900 0.049 Uiso 1 1 calc R U . . .
C00D C 0.4141(7) 0.8944(7) 0.3829(7) 0.0192(13) Uani 1 1 d . . . . .
C00E C 0.7456(8) 0.1314(7) 0.5057(7) 0.0184(13) Uani 1 1 d . . . . .
C00F C 0.2582(8) 1.1451(8) 0.5264(7) 0.0223(14) Uani 1 1 d . . . . .
C00G C 0.3739(8) 1.1586(8) 0.3969(7) 0.0239(15) Uani 1 1 d . . . . .
H00O H 0.4015 1.2528 0.3568 0.029 Uiso 1 1 calc R U . . .
C00H C 0.1517(8) 0.7141(7) 0.7446(6) 0.0246(12) Uani 1 1 d . . . . .
H00P H 0.2297 0.6889 0.8034 0.030 Uiso 1 1 calc R U . . .
C00I C 0.4312(9) 0.6250(9) 0.1944(8) 0.0280(15) Uani 1 1 d . . . . .
C00J C 0.9860(10) 0.4108(9) 0.2280(8) 0.0344(17) Uani 1 1 d . . . . .
H00A H 1.0908 0.3943 0.1584 0.052 Uiso 1 1 calc R U . . .
H00B H 0.9857 0.4648 0.2924 0.052 Uiso 1 1 calc R U . . .
H00C H 0.8967 0.4753 0.1796 0.052 Uiso 1 1 calc R U . . .
C00K C 0.6255(7) 0.1180(8) 0.6369(7) 0.0204(14) Uani 1 1 d . . . . .
C00L C 0.5407(8) 0.2531(8) 0.7098(8) 0.0248(15) Uani 1 1 d . . . . .
H00D H 0.5133 0.3549 0.6394 0.030 Uiso 1 1 calc R U . . .
H00E H 0.4380 0.2407 0.7775 0.030 Uiso 1 1 calc R U . . .
C00M C -0.0824(9) 0.8804(8) 0.9080(7) 0.0319(15) Uani 1 1 d . . . . .
H00Q H -0.1503 0.8124 0.9388 0.048 Uiso 1 1 calc R U . . .
H00S H -0.1531 0.9889 0.9085 0.048 Uiso 1 1 calc R U . . .
H00T H -0.0103 0.8442 0.9723 0.048 Uiso 1 1 calc R U . . .
C00N C 0.0222(7) 0.8734(6) 0.7572(6) 0.0228(11) Uani 1 1 d . . . . .
H00U H -0.0519 0.9035 0.6935 0.027 Uiso 1 1 calc R U . . .
C00O C 0.2950(7) 0.8760(8) 0.5161(7) 0.0184(13) Uani 1 1 d . . . . .
C00P C 0.7820(8) -0.1402(8) 0.5021(7) 0.0231(14) Uani 1 1 d . . . . .
C00Q C 0.2197(7) 1.0015(8) 0.5853(7) 0.0189(13) Uani 1 1 d . . . . .
C00R C 0.6651(8) -0.1491(8) 0.6309(8) 0.0260(16) Uani 1 1 d . . . . .
H00R H 0.6368 -0.2428 0.6731 0.031 Uiso 1 1 calc R U . . .
C00S C 0.8679(10) -0.2771(9) 0.4308(9) 0.0340(17) Uani 1 1 d . . . . .
H00F H 0.8139 -0.3576 0.4784 0.051 Uiso 1 1 calc R U . . .
H00G H 0.9829 -0.3229 0.4366 0.051 Uiso 1 1 calc R U . . .
H00H H 0.8619 -0.2384 0.3318 0.051 Uiso 1 1 calc R U . . .
C00T C 0.7570(9) 0.3742(9) 0.8809(8) 0.0307(15) Uani 1 1 d . . . . .
H00I H 0.7089 0.4367 0.9508 0.046 Uiso 1 1 calc R U . . .
H00J H 0.8398 0.4144 0.8058 0.046 Uiso 1 1 calc R U . . .
H00K H 0.8082 0.2640 0.9262 0.046 Uiso 1 1 calc R U . . .
C00U C 0.2990(9) 0.6300(10) 0.1351(9) 0.0367(17) Uani 1 1 d . . . . .
H00V H 0.3454 0.6193 0.0381 0.055 Uiso 1 1 calc R U . . .
H00W H 0.2103 0.7306 0.1362 0.055 Uiso 1 1 calc R U . . .
H00Y H 0.2558 0.5435 0.1926 0.055 Uiso 1 1 calc R U . . .
C00V C 0.6231(8) 0.3857(9) 0.8185(8) 0.0269(14) Uani 1 1 d . . . . .
C00W C 0.5044(8) 0.7589(9) 0.3102(8) 0.0257(15) Uani 1 1 d . . . . .
H00 H 0.6072 0.7730 0.2439 0.031 Uiso 1 1 calc R U . . .
H H 0.5321 0.6574 0.3809 0.031 Uiso 1 1 calc R U . . .
C00X C 0.9380(7) 0.1647(6) 0.2222(6) 0.0214(11) Uani 1 1 d . . . . .
H00X H 0.8340 0.2278 0.1898 0.026 Uiso 1 1 calc R U . . .
C00Y C 0.5869(8) -0.0259(8) 0.7013(7) 0.0216(14) Uani 1 1 d . . . . .
C00Z C 0.9617(8) 0.2483(7) 0.3133(6) 0.0247(12) Uani 1 1 d . . . . .
H00Z H 1.0619 0.1790 0.3500 0.030 Uiso 1 1 calc R U . . .
C010 C 0.1712(9) 1.2801(8) 0.5992(8) 0.0278(15) Uani 1 1 d . . . . .
H01G H 0.1839 1.2418 0.6964 0.042 Uiso 1 1 calc R U . . .
H01H H 0.0545 1.3204 0.5993 0.042 Uiso 1 1 calc R U . . .
H01I H 0.2192 1.3646 0.5487 0.042 Uiso 1 1 calc R U . . .
C011 C 1.0824(8) 0.1318(9) 0.0940(7) 0.0329(15) Uani 1 1 d . . . . .
H01A H 1.0865 0.2315 0.0251 0.049 Uiso 1 1 calc R U . . .
H01B H 1.0667 0.0649 0.0506 0.049 Uiso 1 1 calc R U . . .
H01C H 1.1853 0.0783 0.1251 0.049 Uiso 1 1 calc R U . . .
C012 C 0.2492(8) 0.7260(7) 0.5882(7) 0.0206(13) Uani 1 1 d . . . . .
C013 C 0.4640(9) -0.0546(10) 0.8435(8) 0.0365(17) Uani 1 1 d . . . . .
H01D H 0.4744 -0.1665 0.8769 0.055 Uiso 1 1 calc R U . . .
H01E H 0.3525 0.0077 0.8317 0.055 Uiso 1 1 calc R U . . .
H01F H 0.4870 -0.0231 0.9125 0.055 Uiso 1 1 calc R U . . .
C014 C 0.0774(10) 0.5780(9) 0.7965(9) 0.0338(16) Uani 1 1 d . . . . .
H01J H 0.1647 0.4800 0.7814 0.051 Uiso 1 1 calc R U . . .
H01K H -0.0042 0.6034 0.7438 0.051 Uiso 1 1 calc R U . . .
H01L H 0.0250 0.5650 0.8971 0.051 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
O001 C009 1.354(9) . ?
O001 C00X 1.443(7) . ?
O002 C00I 1.333(8) . ?
O002 C00W 1.463(8) . ?
O003 C00Q 1.372(9) . ?
O003 C00N 1.462(6) . ?
O004 C00V 1.339(8) . ?
O004 C00L 1.449(8) . ?
O005 C012 1.215(8) . ?
O006 C00B 1.212(8) . ?
O007 C00V 1.187(10) . ?
C008 C00D 1.394(9) . ?
C008 C00G 1.399(10) . ?
C008 C00C 1.509(10) . ?
C009 C00E 1.404(9) . ?
C009 C00P 1.409(9) . ?
O00A C00I 1.218(10) . ?
C00B C00E 1.489(9) . ?
C00B C00Z 1.520(9) . ?
C00C H00L 0.9600 . ?
C00C H00M 0.9600 . ?
C00C H00N 0.9600 . ?
C00D C00O 1.422(9) . ?
C00D C00W 1.501(9) . ?
C00E C00K 1.410(9) . ?
C00F C00G 1.379(10) . ?
C00F C00Q 1.403(9) . ?
C00F C010 1.498(9) . ?
C00G H00O 0.9300 . ?
C00H C00N 1.496(8) . ?
C00H C014 1.528(9) . ?
C00H C012 1.528(9) . ?
C00H H00P 0.9800 . ?
C00I C00U 1.484(10) . ?
C00J C00Z 1.532(9) . ?
C00J H00A 0.9600 . ?
C00J H00B 0.9600 . ?
C00J H00C 0.9600 . ?
C00K C00Y 1.407(9) . ?
C00K C00L 1.498(9) . ?
C00L H00D 0.9700 . ?
C00L H00E 0.9700 . ?
C00M C00N 1.517(9) . ?
C00M H00Q 0.9600 . ?
C00M H00S 0.9600 . ?
C00M H00T 0.9600 . ?
C00N H00U 0.9800 . ?
C00O C00Q 1.401(9) . ?
C00O C012 1.494(9) . ?
C00P C00R 1.377(10) . ?
C00P C00S 1.503(10) . ?
C00R C00Y 1.392(10) . ?
C00R H00R 0.9300 . ?
C00S H00F 0.9600 . ?
C00S H00G 0.9600 . ?
C00S H00H 0.9600 . ?
C00T C00V 1.495(9) . ?
C00T H00I 0.9600 . ?
C00T H00J 0.9600 . ?
C00T H00K 0.9600 . ?
C00U H00V 0.9600 . ?
C00U H00W 0.9600 . ?
C00U H00Y 0.9600 . ?
C00W H00 0.9700 . ?
C00W H 0.9700 . ?
C00X C011 1.517(8) . ?
C00X C00Z 1.520(7) . ?
C00X H00X 0.9800 . ?
C00Y C013 1.510(10) . ?
C00Z H00Z 0.9800 . ?
C010 H01G 0.9600 . ?
C010 H01H 0.9600 . ?
C010 H01I 0.9600 . ?
C011 H01A 0.9600 . ?
C011 H01B 0.9600 . ?
C011 H01C 0.9600 . ?
C013 H01D 0.9600 . ?
C013 H01E 0.9600 . ?
C013 H01F 0.9600 . ?
C014 H01J 0.9600 . ?
C014 H01K 0.9600 . ?
C014 H01L 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C009 O001 C00X 115.8(5) . . ?
C00I O002 C00W 116.4(5) . . ?
C00Q O003 C00N 116.4(5) . . ?
C00V O004 C00L 116.2(5) . . ?
C00D C008 C00G 119.2(6) . . ?
C00D C008 C00C 122.5(7) . . ?
C00G C008 C00C 118.3(6) . . ?
O001 C009 C00E 124.6(5) . . ?
O001 C009 C00P 114.3(6) . . ?
C00E C009 C00P 121.1(6) . . ?
O006 C00B C00E 123.6(6) . . ?
O006 C00B C00Z 121.0(5) . . ?
C00E C00B C00Z 115.2(6) . . ?
C008 C00C H00L 109.5 . . ?
C008 C00C H00M 109.5 . . ?
H00L C00C H00M 109.5 . . ?
C008 C00C H00N 109.5 . . ?
H00L C00C H00N 109.5 . . ?
H00M C00C H00N 109.5 . . ?
C008 C00D C00O 119.4(6) . . ?
C008 C00D C00W 120.0(6) . . ?
C00O C00D C00W 120.5(6) . . ?
C009 C00E C00K 119.9(6) . . ?
C009 C00E C00B 117.0(6) . . ?
C00K C00E C00B 122.9(6) . . ?
C00G C00F C00Q 117.4(6) . . ?
C00G C00F C010 121.7(6) . . ?
C00Q C00F C010 120.8(6) . . ?
C00F C00G C008 123.1(6) . . ?
C00F C00G H00O 118.5 . . ?
C008 C00G H00O 118.5 . . ?
C00N C00H C014 112.9(5) . . ?
C00N C00H C012 109.1(5) . . ?
C014 C00H C012 110.0(5) . . ?
C00N C00H H00P 108.2 . . ?
C014 C00H H00P 108.2 . . ?
C012 C00H H00P 108.2 . . ?
O00A C00I O002 123.3(6) . . ?
O00A C00I C00U 124.6(7) . . ?
O002 C00I C00U 112.0(6) . . ?
C00Z C00J H00A 109.5 . . ?
C00Z C00J H00B 109.5 . . ?
H00A C00J H00B 109.5 . . ?
C00Z C00J H00C 109.5 . . ?
H00A C00J H00C 109.5 . . ?
H00B C00J H00C 109.5 . . ?
C00Y C00K C00E 119.2(7) . . ?
C00Y C00K C00L 119.6(6) . . ?
C00E C00K C00L 121.2(6) . . ?
O004 C00L C00K 108.1(5) . . ?
O004 C00L H00D 110.1 . . ?
C00K C00L H00D 110.1 . . ?
O004 C00L H00E 110.1 . . ?
C00K C00L H00E 110.1 . . ?
H00D C00L H00E 108.4 . . ?
C00N C00M H00Q 109.5 . . ?
C00N C00M H00S 109.5 . . ?
H00Q C00M H00S 109.5 . . ?
C00N C00M H00T 109.5 . . ?
H00Q C00M H00T 109.5 . . ?
H00S C00M H00T 109.5 . . ?
O003 C00N C00H 109.6(4) . . ?
O003 C00N C00M 105.1(5) . . ?
C00H C00N C00M 114.9(5) . . ?
O003 C00N H00U 109.0 . . ?
C00H C00N H00U 109.0 . . ?
C00M C00N H00U 109.0 . . ?
C00Q C00O C00D 119.2(5) . . ?
C00Q C00O C012 118.1(6) . . ?
C00D C00O C012 122.7(6) . . ?
C00R C00P C009 117.3(7) . . ?
C00R C00P C00S 122.4(6) . . ?
C009 C00P C00S 120.3(6) . . ?
O003 C00Q C00O 123.5(5) . . ?
O003 C00Q C00F 114.8(6) . . ?
C00O C00Q C00F 121.7(6) . . ?
C00P C00R C00Y 123.7(6) . . ?
C00P C00R H00R 118.2 . . ?
C00Y C00R H00R 118.2 . . ?
C00P C00S H00F 109.5 . . ?
C00P C00S H00G 109.5 . . ?
H00F C00S H00G 109.5 . . ?
C00P C00S H00H 109.5 . . ?
H00F C00S H00H 109.5 . . ?
H00G C00S H00H 109.5 . . ?
C00V C00T H00I 109.5 . . ?
C00V C00T H00J 109.5 . . ?
H00I C00T H00J 109.5 . . ?
C00V C00T H00K 109.5 . . ?
H00I C00T H00K 109.5 . . ?
H00J C00T H00K 109.5 . . ?
C00I C00U H00V 109.5 . . ?
C00I C00U H00W 109.5 . . ?
H00V C00U H00W 109.5 . . ?
C00I C00U H00Y 109.5 . . ?
H00V C00U H00Y 109.5 . . ?
H00W C00U H00Y 109.5 . . ?
O007 C00V O004 124.5(6) . . ?
O007 C00V C00T 123.9(7) . . ?
O004 C00V C00T 111.6(6) . . ?
O002 C00W C00D 107.8(5) . . ?
O002 C00W H00 110.1 . . ?
C00D C00W H00 110.1 . . ?
O002 C00W H 110.1 . . ?
C00D C00W H 110.1 . . ?
H00 C00W H 108.5 . . ?
O001 C00X C011 104.7(5) . . ?
O001 C00X C00Z 108.4(4) . . ?
C011 C00X C00Z 114.3(5) . . ?
O001 C00X H00X 109.8 . . ?
C011 C00X H00X 109.8 . . ?
C00Z C00X H00X 109.8 . . ?
C00R C00Y C00K 118.8(6) . . ?
C00R C00Y C013 117.7(6) . . ?
C00K C00Y C013 123.5(7) . . ?
C00X C00Z C00B 109.3(4) . . ?
C00X C00Z C00J 112.7(5) . . ?
C00B C00Z C00J 110.5(5) . . ?
C00X C00Z H00Z 108.0 . . ?
C00B C00Z H00Z 108.0 . . ?
C00J C00Z H00Z 108.0 . . ?
C00F C010 H01G 109.5 . . ?
C00F C010 H01H 109.5 . . ?
H01G C010 H01H 109.5 . . ?
C00F C010 H01I 109.5 . . ?
H01G C010 H01I 109.5 . . ?
H01H C010 H01I 109.5 . . ?
C00X C011 H01A 109.5 . . ?
C00X C011 H01B 109.5 . . ?
H01A C011 H01B 109.5 . . ?
C00X C011 H01C 109.5 . . ?
H01A C011 H01C 109.5 . . ?
H01B C011 H01C 109.5 . . ?
O005 C012 C00O 123.6(6) . . ?
O005 C012 C00H 121.8(5) . . ?
C00O C012 C00H 114.6(6) . . ?
C00Y C013 H01D 109.5 . . ?
C00Y C013 H01E 109.5 . . ?
H01D C013 H01E 109.5 . . ?
C00Y C013 H01F 109.5 . . ?
H01D C013 H01F 109.5 . . ?
H01E C013 H01F 109.5 . . ?
C00H C014 H01J 109.5 . . ?
C00H C014 H01K 109.5 . . ?
H01J C014 H01K 109.5 . . ?
C00H C014 H01L 109.5 . . ?
H01J C014 H01L 109.5 . . ?
H01K C014 H01L 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
C00X O001 C009 C00E -17.2(9) . . . . ?
C00X O001 C009 C00P 164.3(5) . . . . ?
C00G C008 C00D C00O 1.3(9) . . . . ?
C00C C008 C00D C00O -178.6(6) . . . . ?
C00G C008 C00D C00W -176.0(5) . . . . ?
C00C C008 C00D C00W 4.1(9) . . . . ?
O001 C009 C00E C00K 177.4(6) . . . . ?
C00P C009 C00E C00K -4.2(9) . . . . ?
O001 C009 C00E C00B -8.5(9) . . . . ?
C00P C009 C00E C00B 170.0(6) . . . . ?
O006 C00B C00E C009 -178.4(6) . . . . ?
C00Z C00B C00E C009 -3.8(8) . . . . ?
O006 C00B C00E C00K -4.5(10) . . . . ?
C00Z C00B C00E C00K 170.2(6) . . . . ?
C00Q C00F C00G C008 0.5(10) . . . . ?
C010 C00F C00G C008 -177.0(5) . . . . ?
C00D C008 C00G C00F -1.1(10) . . . . ?
C00C C008 C00G C00F 178.7(6) . . . . ?
C00W O002 C00I O00A -7.7(10) . . . . ?
C00W O002 C00I C00U 171.9(6) . . . . ?
C009 C00E C00K C00Y 3.3(9) . . . . ?
C00B C00E C00K C00Y -170.4(6) . . . . ?
C009 C00E C00K C00L -177.7(5) . . . . ?
C00B C00E C00K C00L 8.5(9) . . . . ?
C00V O004 C00L C00K 160.4(5) . . . . ?
C00Y C00K C00L O004 99.4(6) . . . . ?
C00E C00K C00L O004 -79.5(7) . . . . ?
C00Q O003 C00N C00H 49.7(7) . . . . ?
C00Q O003 C00N C00M 173.7(5) . . . . ?
C014 C00H C00N O003 176.6(6) . . . . ?
C012 C00H C00N O003 -60.8(6) . . . . ?
C014 C00H C00N C00M 58.5(7) . . . . ?
C012 C00H C00N C00M -178.8(5) . . . . ?
C008 C00D C00O C00Q -0.9(9) . . . . ?
C00W C00D C00O C00Q 176.4(5) . . . . ?
C008 C00D C00O C012 -179.2(5) . . . . ?
C00W C00D C00O C012 -1.9(9) . . . . ?
O001 C009 C00P C00R -177.9(6) . . . . ?
C00E C009 C00P C00R 3.6(9) . . . . ?
O001 C009 C00P C00S 1.7(9) . . . . ?
C00E C009 C00P C00S -176.9(5) . . . . ?
C00N O003 C00Q C00O -18.0(8) . . . . ?
C00N O003 C00Q C00F 161.9(5) . . . . ?
C00D C00O C00Q O003 -179.9(6) . . . . ?
C012 C00O C00Q O003 -1.5(9) . . . . ?
C00D C00O C00Q C00F 0.2(9) . . . . ?
C012 C00O C00Q C00F 178.7(5) . . . . ?
C00G C00F C00Q O003 -179.9(6) . . . . ?
C010 C00F C00Q O003 -2.3(8) . . . . ?
C00G C00F C00Q C00O 0.0(9) . . . . ?
C010 C00F C00Q C00O 177.5(5) . . . . ?
C009 C00P C00R C00Y -2.3(10) . . . . ?
C00S C00P C00R C00Y 178.2(5) . . . . ?
C00L O004 C00V O007 4.3(11) . . . . ?
C00L O004 C00V C00T -174.0(6) . . . . ?
C00I O002 C00W C00D -162.1(5) . . . . ?
C008 C00D C00W O002 -101.2(6) . . . . ?
C00O C00D C00W O002 81.5(7) . . . . ?
C009 O001 C00X C011 174.5(5) . . . . ?
C009 O001 C00X C00Z 52.1(6) . . . . ?
C00P C00R C00Y C00K 1.6(9) . . . . ?
C00P C00R C00Y C013 -178.7(6) . . . . ?
C00E C00K C00Y C00R -2.0(9) . . . . ?
C00L C00K C00Y C00R 179.0(5) . . . . ?
C00E C00K C00Y C013 178.2(6) . . . . ?
C00L C00K C00Y C013 -0.7(9) . . . . ?
O001 C00X C00Z C00B -61.4(6) . . . . ?
C011 C00X C00Z C00B -177.6(6) . . . . ?
O001 C00X C00Z C00J 175.3(5) . . . . ?
C011 C00X C00Z C00J 59.0(7) . . . . ?
O006 C00B C00Z C00X -147.4(6) . . . . ?
C00E C00B C00Z C00X 37.8(7) . . . . ?
O006 C00B C00Z C00J -22.8(9) . . . . ?
C00E C00B C00Z C00J 162.4(6) . . . . ?
C00Q C00O C012 O005 168.0(6) . . . . ?
C00D C00O C012 O005 -13.6(10) . . . . ?
C00Q C00O C012 C00H -12.0(8) . . . . ?
C00D C00O C012 C00H 166.4(6) . . . . ?
C00N C00H C012 O005 -137.3(6) . . . . ?
C014 C00H C012 O005 -13.0(8) . . . . ?
C00N C00H C012 C00O 42.7(7) . . . . ?
C014 C00H C012 C00O 167.0(5) . . . . ?

_refine_diff_density_max         0.250
_refine_diff_density_min         -0.303
_refine_diff_density_rms         0.069

####################################################################### 
# 
# 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_cu_20181016_0m_a
_database_code_depnum_ccdc_archive 'CCDC 1873977'
_audit_update_record             
;
2018-10-18 deposited with the CCDC.
2019-01-14 downloaded from the CCDC.
;
_audit_creation_date             2018-10-18
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C13 H16 O6'
_chemical_formula_sum            'C13 H16 O6'
_chemical_formula_weight         268.26
_chemical_absolute_configuration .
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   12.4892(3)
_cell_length_b                   13.7293(4)
_cell_length_c                   14.9296(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2559.95(12)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    9827
_cell_measurement_temperature    293.15
_cell_measurement_theta_max      71.865
_cell_measurement_theta_min      4.375
_shelx_estimated_absorpt_T_max   0.912
_shelx_estimated_absorpt_T_min   0.912
_exptl_absorpt_coefficient_mu    0.939
_exptl_absorpt_correction_T_max  0.7536
_exptl_absorpt_correction_T_min  0.3135
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2014/5 (Bruker,2014/5) was used for absorption correction. wR2(int) was 0.1877 before and 0.1078 after correction. The Ratio of minimum to maximum transmission is 0.4160. The λ/2 correction factor is 0.00150.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.392
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1136
_exptl_crystal_preparation       ?
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1538
_diffrn_reflns_av_unetI/netI     0.0888
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            26351
_diffrn_reflns_point_group_measured_fraction_full 0.983
_diffrn_reflns_point_group_measured_fraction_max 0.983
_diffrn_reflns_theta_full        66.561
_diffrn_reflns_theta_max         66.561
_diffrn_reflns_theta_min         4.375
_diffrn_ambient_temperature      293.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   ?
_diffrn_special_details          ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.748
_reflns_Friedel_fraction_full    0.970
_reflns_Friedel_fraction_max     0.970
_reflns_number_gt                3569
_reflns_number_total             4435
_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. Completness statistics refer to single and
 composite reflections containing twin component 1 only.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.648
_refine_diff_density_min         -0.582
_refine_diff_density_rms         0.144
_refine_ls_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.4(5)
_refine_ls_extinction_coef       0.0030(12)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     356
_refine_ls_number_reflns         4435
_refine_ls_number_restraints     4
_refine_ls_R_factor_all          0.1066
_refine_ls_R_factor_gt           0.0910
_refine_ls_restrained_S_all      1.042
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.2000P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2401
_refine_ls_wR_factor_ref         0.2633
_refine_special_details          
;
 Refined as a 2-component inversion twin.
;
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 0.6(5)
 0.4(5)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
3. Restrained distances
 H5-O8_$1
 2.2 with sigma of 0.02
 H5_$2-H12
 2.2 with sigma of 0.02
 H9-O8
 2.4 with sigma of 0.02
 H12A_$3-H9
 2.2 with sigma of 0.02
4.a Riding coordinates:
 O9(H9)
4.b Ternary CH refined with riding coordinates:
 C23(H23), C10(H10)
4.c Secondary CH2 refined with riding coordinates:
 C24(H24A,H24B), C11(H11A,H11B)
4.d Aromatic/amide H refined with riding coordinates:
 C17(H17), C4(H4)
4.e Idealised Me refined as rotating group:
 C26(H26A,H26B,H26C), C25(H25A,H25B,H25C), C19(H19A,H19B,H19C), C13(H13A,H13B,
 H13C), C12(H12A,H12B,H12C), C6(H6A,H6B,H6C)
4.f Idealised tetrahedral OH refined as rotating group:
 O11(H11), O12(H12), O3(H3), O5(H5), O6(H6)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O11 O 0.4080(4) 0.1195(4) 0.3551(3) 0.0256(11) Uani 1 1 d . . . . .
H11 H 0.432193 0.064131 0.350801 0.038 Uiso 1 1 calc GR . . . .
O9 O 0.6926(4) 0.4975(4) 0.4785(4) 0.0357(13) Uani 1 1 d . . . . .
H9 H 0.673076 0.507142 0.426835 0.054 Uiso 1 1 d DR . . . .
O7 O 0.4532(4) 0.3165(4) 0.3591(3) 0.0286(11) Uani 1 1 d . . . . .
O12 O 0.5899(4) 0.0459(4) 0.4529(4) 0.0368(13) Uani 1 1 d . . . . .
H12 H 0.604607 0.023867 0.403378 0.055 Uiso 1 1 calc DGR . . . .
O10 O 0.5293(4) 0.3698(5) 0.7456(3) 0.0387(14) Uani 1 1 d . . . . .
O8 O 0.5681(4) 0.4317(5) 0.3151(3) 0.0382(13) Uani 1 1 d D . . . .
C16 C 0.6195(5) 0.4437(5) 0.5212(5) 0.0243(14) Uani 1 1 d . . . . .
C22 C 0.4147(5) 0.2710(5) 0.4414(5) 0.0221(14) Uani 1 1 d . . . . .
C15 C 0.5461(5) 0.3890(5) 0.4728(4) 0.0252(15) Uani 1 1 d . . . . .
C14 C 0.5286(5) 0.3846(5) 0.3763(5) 0.0257(15) Uani 1 1 d . . . . .
C21 C 0.4739(5) 0.3255(6) 0.5147(5) 0.0242(14) Uani 1 1 d . . . . .
C23 C 0.4458(5) 0.1634(5) 0.4367(5) 0.0252(15) Uani 1 1 d . . . . .
H23 H 0.410863 0.130006 0.486850 0.030 Uiso 1 1 calc R . . . .
C18 C 0.5398(5) 0.3775(5) 0.6553(4) 0.0264(15) Uani 1 1 d . . . . .
C20 C 0.4671(5) 0.3174(6) 0.6061(4) 0.0270(15) Uani 1 1 d . . . . .
C17 C 0.6149(5) 0.4361(6) 0.6145(5) 0.0266(15) Uani 1 1 d . . . . .
H17 H 0.663157 0.470985 0.649506 0.032 Uiso 1 1 calc R . . . .
C26 C 0.3909(6) 0.2501(7) 0.6564(6) 0.0383(19) Uani 1 1 d . . . . .
H26A H 0.341315 0.288366 0.690705 0.057 Uiso 1 1 calc GR . . . .
H26B H 0.431152 0.208824 0.695960 0.057 Uiso 1 1 calc GR . . . .
H26C H 0.352225 0.210638 0.614328 0.057 Uiso 1 1 calc GR . . . .
C24 C 0.5661(5) 0.1467(6) 0.4453(5) 0.0314(17) Uani 1 1 d . . . . .
H24A H 0.602080 0.173104 0.393081 0.038 Uiso 1 1 calc R . . . .
H24B H 0.592738 0.180669 0.497703 0.038 Uiso 1 1 calc R . . . .
C25 C 0.2930(5) 0.2811(6) 0.4412(6) 0.0346(18) Uani 1 1 d . . . . .
H25A H 0.274128 0.348857 0.440905 0.052 Uiso 1 1 calc GR . . . .
H25B H 0.264158 0.250652 0.493824 0.052 Uiso 1 1 calc GR . . . .
H25C H 0.264280 0.250114 0.388821 0.052 Uiso 1 1 calc GR . . . .
C19 C 0.5972(7) 0.4307(8) 0.8004(6) 0.047(2) Uani 1 1 d . . . . .
H19A H 0.670700 0.420593 0.783973 0.071 Uiso 1 1 calc GR . . . .
H19B H 0.587395 0.414157 0.862296 0.071 Uiso 1 1 calc GR . . . .
H19C H 0.578647 0.497820 0.791210 0.071 Uiso 1 1 calc GR . . . .
O1 O 0.9730(3) 0.8113(4) 0.7011(3) 0.0258(11) Uani 1 1 d . . . . .
O3 O 0.7248(4) 0.9757(4) 0.5711(3) 0.0315(12) Uani 1 1 d . . . . .
H3 H 0.680949 0.991288 0.532839 0.047 Uiso 1 1 calc GR . . . .
O5 O 1.0520(4) 0.6037(4) 0.6612(3) 0.0273(11) Uani 1 1 d . . . . .
H5 H 1.010083 0.566552 0.686054 0.041 Uiso 1 1 calc DGR . . . .
O6 O 0.8452(4) 0.5561(5) 0.5870(4) 0.0411(15) Uani 1 1 d . . . . .
H6 H 0.781286 0.554442 0.574430 0.062 Uiso 1 1 calc GR . . . .
O4 O 0.9329(4) 0.8828(4) 0.3119(3) 0.0323(12) Uani 1 1 d . . . . .
O2 O 0.8370(4) 0.9084(5) 0.7419(3) 0.0374(14) Uani 1 1 d . . . . .
C3 C 0.8109(5) 0.9347(5) 0.5312(5) 0.0251(15) Uani 1 1 d . . . . .
C7 C 0.9887(5) 0.8349(5) 0.4541(5) 0.0239(14) Uani 1 1 d . . . . .
C10 C 0.9947(5) 0.6673(5) 0.6040(5) 0.0223(14) Uani 1 1 d . . . . .
H10 H 1.013813 0.649993 0.542334 0.027 Uiso 1 1 calc R . . . .
C2 C 0.8861(5) 0.8868(6) 0.5843(4) 0.0230(14) Uani 1 1 d . . . . .
C8 C 0.9713(5) 0.8363(5) 0.5454(4) 0.0212(13) Uani 1 1 d . . . . .
C1 C 0.8897(5) 0.8741(6) 0.6813(5) 0.0273(16) Uani 1 1 d . . . . .
C4 C 0.8254(5) 0.9347(6) 0.4395(5) 0.0269(15) Uani 1 1 d . . . . .
H4 H 0.776990 0.966802 0.402515 0.032 Uiso 1 1 calc R . . . .
C13 C 1.0804(5) 0.7834(6) 0.4085(5) 0.0288(16) Uani 1 1 d . . . . .
H13A H 1.125550 0.830476 0.379638 0.043 Uiso 1 1 calc GR . . . .
H13B H 1.052711 0.738927 0.364621 0.043 Uiso 1 1 calc GR . . . .
H13C H 1.121201 0.748053 0.452216 0.043 Uiso 1 1 calc GR . . . .
C9 C 1.0260(5) 0.7766(5) 0.6175(4) 0.0233(15) Uani 1 1 d . . . . .
C5 C 0.9139(5) 0.8857(6) 0.4022(4) 0.0264(16) Uani 1 1 d . . . . .
C12 C 1.1449(5) 0.7928(6) 0.6327(5) 0.0315(17) Uani 1 1 d . . . . .
H12A H 1.173249 0.832342 0.585249 0.047 Uiso 1 1 calc DGR . . . .
H12B H 1.181112 0.731092 0.633344 0.047 Uiso 1 1 calc GR . . . .
H12C H 1.155572 0.825094 0.688993 0.047 Uiso 1 1 calc GR . . . .
C11 C 0.8740(5) 0.6525(6) 0.6133(6) 0.0346(18) Uani 1 1 d . . . . .
H11A H 0.852749 0.663441 0.674940 0.042 Uiso 1 1 calc R . . . .
H11B H 0.836541 0.699259 0.575946 0.042 Uiso 1 1 calc R . . . .
C6 C 0.8573(6) 0.9279(7) 0.2536(5) 0.0368(19) Uani 1 1 d . . . . .
H6A H 0.880625 0.920704 0.192658 0.055 Uiso 1 1 calc GR . . . .
H6B H 0.851769 0.995830 0.267959 0.055 Uiso 1 1 calc GR . . . .
H6C H 0.788667 0.897426 0.260849 0.055 Uiso 1 1 calc GR . . . .


_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
O11 H11 0.8200 . ?
O11 C23 1.440(8) . ?
O9 H9 0.8200 . ?
O9 C16 1.336(9) . ?
O7 C22 1.459(8) . ?
O7 C14 1.352(9) . ?
O12 H12 0.8200 . ?
O12 C24 1.420(10) . ?
O10 C18 1.359(9) . ?
O10 C19 1.444(11) . ?
O8 C14 1.223(9) . ?
C16 C15 1.389(10) . ?
C16 C17 1.398(10) . ?
C22 C21 1.519(9) . ?
C22 C23 1.528(10) . ?
C22 C25 1.526(8) . ?
C15 C14 1.459(9) . ?
C15 C21 1.402(10) . ?
C21 C20 1.372(9) . ?
C23 H23 0.9800 . ?
C23 C24 1.525(9) . ?
C18 C20 1.430(10) . ?
C18 C17 1.377(10) . ?
C20 C26 1.524(11) . ?
C17 H17 0.9300 . ?
C26 H26A 0.9600 . ?
C26 H26B 0.9600 . ?
C26 H26C 0.9600 . ?
C24 H24A 0.9700 . ?
C24 H24B 0.9700 . ?
C25 H25A 0.9600 . ?
C25 H25B 0.9600 . ?
C25 H25C 0.9600 . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
O1 C1 1.382(8) . ?
O1 C9 1.491(8) . ?
O3 H3 0.8200 . ?
O3 C3 1.352(8) . ?
O5 H5 0.8200 . ?
O5 C10 1.417(8) . ?
O6 H6 0.8200 . ?
O6 C11 1.427(10) . ?
O4 C5 1.370(8) . ?
O4 C6 1.425(9) . ?
O2 C1 1.214(9) . ?
C3 C2 1.393(10) . ?
C3 C4 1.382(10) . ?
C7 C8 1.381(10) . ?
C7 C13 1.508(10) . ?
C7 C5 1.400(9) . ?
C10 H10 0.9800 . ?
C10 C9 1.564(10) . ?
C10 C11 1.527(8) . ?
C2 C8 1.397(9) . ?
C2 C1 1.459(9) . ?
C8 C9 1.516(9) . ?
C4 H4 0.9300 . ?
C4 C5 1.407(10) . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C9 C12 1.518(8) . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C6 H6A 0.9600 . ?
C6 H6B 0.9600 . ?
C6 H6C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C23 O11 H11 109.5 . . ?
C16 O9 H9 109.6 . . ?
C14 O7 C22 111.5(5) . . ?
C24 O12 H12 109.5 . . ?
C18 O10 C19 117.4(7) . . ?
O9 C16 C15 120.1(6) . . ?
O9 C16 C17 123.1(6) . . ?
C15 C16 C17 116.8(6) . . ?
O7 C22 C21 103.6(5) . . ?
O7 C22 C23 107.0(5) . . ?
O7 C22 C25 106.7(6) . . ?
C21 C22 C23 112.7(5) . . ?
C21 C22 C25 116.1(6) . . ?
C25 C22 C23 109.9(6) . . ?
C16 C15 C14 129.5(7) . . ?
C16 C15 C21 121.9(6) . . ?
C21 C15 C14 108.6(6) . . ?
O7 C14 C15 108.7(6) . . ?
O8 C14 O7 120.3(6) . . ?
O8 C14 C15 131.0(7) . . ?
C15 C21 C22 107.3(6) . . ?
C20 C21 C22 130.3(7) . . ?
C20 C21 C15 122.3(7) . . ?
O11 C23 C22 111.1(5) . . ?
O11 C23 H23 107.7 . . ?
O11 C23 C24 109.3(6) . . ?
C22 C23 H23 107.7 . . ?
C24 C23 C22 113.1(6) . . ?
C24 C23 H23 107.7 . . ?
O10 C18 C20 113.8(6) . . ?
O10 C18 C17 123.3(7) . . ?
C17 C18 C20 122.9(6) . . ?
C21 C20 C18 115.1(6) . . ?
C21 C20 C26 125.3(7) . . ?
C18 C20 C26 119.6(6) . . ?
C16 C17 H17 119.6 . . ?
C18 C17 C16 120.8(6) . . ?
C18 C17 H17 119.6 . . ?
C20 C26 H26A 109.5 . . ?
C20 C26 H26B 109.5 . . ?
C20 C26 H26C 109.5 . . ?
H26A C26 H26B 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
O12 C24 C23 111.1(6) . . ?
O12 C24 H24A 109.4 . . ?
O12 C24 H24B 109.4 . . ?
C23 C24 H24A 109.4 . . ?
C23 C24 H24B 109.4 . . ?
H24A C24 H24B 108.0 . . ?
C22 C25 H25A 109.5 . . ?
C22 C25 H25B 109.5 . . ?
C22 C25 H25C 109.5 . . ?
H25A C25 H25B 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
O10 C19 H19A 109.5 . . ?
O10 C19 H19B 109.5 . . ?
O10 C19 H19C 109.5 . . ?
H19A C19 H19B 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C1 O1 C9 110.7(5) . . ?
C3 O3 H3 109.5 . . ?
C10 O5 H5 109.5 . . ?
C11 O6 H6 109.5 . . ?
C5 O4 C6 118.3(6) . . ?
O3 C3 C2 118.8(6) . . ?
O3 C3 C4 122.8(6) . . ?
C4 C3 C2 118.4(6) . . ?
C8 C7 C13 124.9(6) . . ?
C8 C7 C5 115.7(6) . . ?
C5 C7 C13 119.4(6) . . ?
O5 C10 H10 107.1 . . ?
O5 C10 C9 112.7(5) . . ?
O5 C10 C11 111.2(6) . . ?
C9 C10 H10 107.1 . . ?
C11 C10 H10 107.1 . . ?
C11 C10 C9 111.3(6) . . ?
C3 C2 C8 120.8(6) . . ?
C3 C2 C1 129.9(6) . . ?
C8 C2 C1 109.2(6) . . ?
C7 C8 C2 122.5(6) . . ?
C7 C8 C9 128.5(6) . . ?
C2 C8 C9 108.5(5) . . ?
O1 C1 C2 108.1(6) . . ?
O2 C1 O1 119.3(6) . . ?
O2 C1 C2 132.5(7) . . ?
C3 C4 H4 120.2 . . ?
C3 C4 C5 119.7(6) . . ?
C5 C4 H4 120.2 . . ?
C7 C13 H13A 109.5 . . ?
C7 C13 H13B 109.5 . . ?
C7 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
O1 C9 C10 107.7(5) . . ?
O1 C9 C8 102.8(5) . . ?
O1 C9 C12 105.3(5) . . ?
C8 C9 C10 108.3(5) . . ?
C8 C9 C12 117.9(6) . . ?
C12 C9 C10 113.8(6) . . ?
O4 C5 C7 114.5(6) . . ?
O4 C5 C4 122.6(6) . . ?
C7 C5 C4 122.9(6) . . ?
C9 C12 H12A 109.5 . . ?
C9 C12 H12B 109.5 . . ?
C9 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
O6 C11 C10 110.3(6) . . ?
O6 C11 H11A 109.6 . . ?
O6 C11 H11B 109.6 . . ?
C10 C11 H11A 109.6 . . ?
C10 C11 H11B 109.6 . . ?
H11A C11 H11B 108.1 . . ?
O4 C6 H6A 109.5 . . ?
O4 C6 H6B 109.5 . . ?
O4 C6 H6C 109.5 . . ?
H6A C6 H6B 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 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 C23 C24 O12 -63.7(8) . . . . ?
O9 C16 C15 C14 -5.0(12) . . . . ?
O9 C16 C15 C21 174.6(6) . . . . ?
O9 C16 C17 C18 -178.2(6) . . . . ?
O7 C22 C21 C15 -5.2(7) . . . . ?
O7 C22 C21 C20 177.0(7) . . . . ?
O7 C22 C23 O11 -53.5(6) . . . . ?
O7 C22 C23 C24 69.8(7) . . . . ?
O10 C18 C20 C21 178.4(6) . . . . ?
O10 C18 C20 C26 -2.3(10) . . . . ?
O10 C18 C17 C16 -177.8(7) . . . . ?
C16 C15 C14 O7 176.1(7) . . . . ?
C16 C15 C14 O8 -5.6(13) . . . . ?
C16 C15 C21 C22 -174.3(6) . . . . ?
C16 C15 C21 C20 3.7(11) . . . . ?
C22 O7 C14 O8 -178.4(6) . . . . ?
C22 O7 C14 C15 0.1(7) . . . . ?
C22 C21 C20 C18 176.8(7) . . . . ?
C22 C21 C20 C26 -2.5(13) . . . . ?
C22 C23 C24 O12 172.0(6) . . . . ?
C15 C16 C17 C18 -0.7(11) . . . . ?
C15 C21 C20 C18 -0.7(11) . . . . ?
C15 C21 C20 C26 -180.0(7) . . . . ?
C14 O7 C22 C21 3.1(7) . . . . ?
C14 O7 C22 C23 -116.2(6) . . . . ?
C14 O7 C22 C25 126.2(6) . . . . ?
C14 C15 C21 C22 5.4(8) . . . . ?
C14 C15 C21 C20 -176.6(7) . . . . ?
C21 C22 C23 O11 -166.8(5) . . . . ?
C21 C22 C23 C24 -43.5(8) . . . . ?
C21 C15 C14 O7 -3.6(8) . . . . ?
C21 C15 C14 O8 174.7(8) . . . . ?
C23 C22 C21 C15 110.1(7) . . . . ?
C23 C22 C21 C20 -67.7(9) . . . . ?
C20 C18 C17 C16 3.8(11) . . . . ?
C17 C16 C15 C14 177.4(7) . . . . ?
C17 C16 C15 C21 -3.0(11) . . . . ?
C17 C18 C20 C21 -3.0(11) . . . . ?
C17 C18 C20 C26 176.3(7) . . . . ?
C25 C22 C21 C15 -121.8(7) . . . . ?
C25 C22 C21 C20 60.4(11) . . . . ?
C25 C22 C23 O11 62.0(7) . . . . ?
C25 C22 C23 C24 -174.7(6) . . . . ?
C19 O10 C18 C20 -177.9(7) . . . . ?
C19 O10 C18 C17 3.5(11) . . . . ?
O3 C3 C2 C8 174.5(6) . . . . ?
O3 C3 C2 C1 -1.5(12) . . . . ?
O3 C3 C4 C5 -176.4(7) . . . . ?
O5 C10 C9 O1 -76.8(6) . . . . ?
O5 C10 C9 C8 172.7(5) . . . . ?
O5 C10 C9 C12 39.5(8) . . . . ?
O5 C10 C11 O6 -62.4(8) . . . . ?
C3 C2 C8 C7 3.2(10) . . . . ?
C3 C2 C8 C9 -169.2(6) . . . . ?
C3 C2 C1 O1 172.8(7) . . . . ?
C3 C2 C1 O2 -8.7(14) . . . . ?
C3 C4 C5 O4 179.9(7) . . . . ?
C3 C4 C5 C7 0.9(11) . . . . ?
C7 C8 C9 O1 179.9(6) . . . . ?
C7 C8 C9 C10 -66.4(8) . . . . ?
C7 C8 C9 C12 64.6(10) . . . . ?
C2 C3 C4 C5 0.9(11) . . . . ?
C2 C8 C9 O1 -8.3(7) . . . . ?
C2 C8 C9 C10 105.5(6) . . . . ?
C2 C8 C9 C12 -123.5(7) . . . . ?
C8 C7 C5 O4 -179.8(6) . . . . ?
C8 C7 C5 C4 -0.7(10) . . . . ?
C8 C2 C1 O1 -3.5(8) . . . . ?
C8 C2 C1 O2 174.9(8) . . . . ?
C1 O1 C9 C10 -107.9(6) . . . . ?
C1 O1 C9 C8 6.3(7) . . . . ?
C1 O1 C9 C12 130.3(6) . . . . ?
C1 C2 C8 C7 179.9(6) . . . . ?
C1 C2 C8 C9 7.5(8) . . . . ?
C4 C3 C2 C8 -2.9(11) . . . . ?
C4 C3 C2 C1 -178.8(7) . . . . ?
C13 C7 C8 C2 178.8(6) . . . . ?
C13 C7 C8 C9 -10.4(11) . . . . ?
C13 C7 C5 O4 0.1(10) . . . . ?
C13 C7 C5 C4 179.2(7) . . . . ?
C9 O1 C1 O2 179.2(7) . . . . ?
C9 O1 C1 C2 -2.1(7) . . . . ?
C9 C10 C11 O6 171.0(6) . . . . ?
C5 C7 C8 C2 -1.4(10) . . . . ?
C5 C7 C8 C9 169.4(7) . . . . ?
C11 C10 C9 O1 49.0(7) . . . . ?
C11 C10 C9 C8 -61.5(7) . . . . ?
C11 C10 C9 C12 165.3(6) . . . . ?
C6 O4 C5 C7 176.5(7) . . . . ?
C6 O4 C5 C4 -2.6(11) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 0.6(5)
2 0.4(5)

