# 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_20180707_0m_a
_database_code_depnum_ccdc_archive 'CCDC 1874967'
loop_
_audit_author_name
_audit_author_address
'Gang Li'
;No. 38, Dengzhou Road, Qingdao University, Qingdao 266021
China
;
_audit_update_record             
;
2018-10-24 deposited with the CCDC.	2019-04-15 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C15 H20 O6'
_chemical_formula_weight         296.31

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                   5.3125(2)
_cell_length_b                   7.9672(3)
_cell_length_c                   16.2923(7)
_cell_angle_alpha                90
_cell_angle_beta                 96.610(2)
_cell_angle_gamma                90
_cell_volume                     685.00(5)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.437
_exptl_crystal_F_000             316
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_absorpt_coefficient_mu    0.930
_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  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            5212
_diffrn_reflns_av_unetI/netI     0.0617
_diffrn_reflns_av_R_equivalents  0.0643
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.730
_diffrn_reflns_theta_max         57.890
_diffrn_reflns_theta_full        57.890
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measured_fraction_theta_full 0.983
_diffrn_reflns_Laue_measured_fraction_max 0.983
_diffrn_reflns_Laue_measured_fraction_full 0.983
_diffrn_reflns_point_group_measured_fraction_max 0.962
_diffrn_reflns_point_group_measured_fraction_full 0.962
_reflns_number_total             1831
_reflns_number_gt                1742
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.806
_reflns_Friedel_fraction_max     0.938
_reflns_Friedel_fraction_full    0.938

_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+(0.1039P)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 736 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.12(14)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         1831
_refine_ls_number_parameters     197
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0573
_refine_ls_R_factor_gt           0.0544
_refine_ls_wR_factor_ref         0.1467
_refine_ls_wR_factor_gt          0.1438
_refine_ls_goodness_of_fit_ref   1.157
_refine_ls_restrained_S_all      1.156
_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 0.3769(6) 0.2510(4) 0.5220(2) 0.0203(8) Uani 1 1 d . . . . .
H001 H 0.394(11) 0.226(4) 0.476(4) 0.031 Uiso 1 1 calc R U . . .
O002 O 0.7244(7) 0.1817(4) 0.8435(2) 0.0311(9) Uani 1 1 d . . . . .
O003 O 0.5270(7) 0.0692(4) 0.6634(2) 0.0270(9) Uani 1 1 d . . . . .
H003 H 0.4942 0.1068 0.6165 0.041 Uiso 1 1 calc R U . . .
O004 O 0.5451(6) 0.7247(4) 0.6446(2) 0.0231(8) Uani 1 1 d . . . . .
H004 H 0.5266 0.8226 0.6583 0.035 Uiso 1 1 calc R U . . .
O005 O 1.0920(7) 0.3339(4) 0.9258(2) 0.0285(9) Uani 1 1 d . . . . .
H005 H 1.0119 0.2524 0.9064 0.043 Uiso 1 1 calc R U . . .
O006 O 1.1641(6) 0.9193(4) 0.8799(2) 0.0310(9) Uani 1 1 d . . . . .
C007 C 0.7268(8) 0.6177(6) 0.7793(3) 0.0182(10) Uani 1 1 d . . . . .
C008 C 0.7962(9) 0.4683(6) 0.8222(3) 0.0206(10) Uani 1 1 d . . . . .
C009 C 1.1328(9) 0.6212(7) 0.9057(3) 0.0252(11) Uani 1 1 d . . . . .
H009 H 1.2677 0.6233 0.9475 0.030 Uiso 1 1 calc R U . . .
C00A C 0.5033(8) 0.6166(6) 0.7114(3) 0.0174(10) Uani 1 1 d . . . . .
H00A H 0.3531 0.6566 0.7352 0.021 Uiso 1 1 calc R U . . .
C00B C 0.3530(9) 0.1359(6) 0.7153(3) 0.0244(11) Uani 1 1 d . . . . .
H00B H 0.3499 0.0637 0.7631 0.029 Uiso 1 1 calc R U . . .
H00C H 0.1843 0.1364 0.6853 0.029 Uiso 1 1 calc R U . . .
C00C C 0.4224(8) 0.3140(6) 0.7444(3) 0.0201(11) Uani 1 1 d . . . . .
H00D H 0.2837 0.3530 0.7743 0.024 Uiso 1 1 calc R U . . .
C00D C 1.0080(8) 0.4731(6) 0.8846(3) 0.0207(11) Uani 1 1 d . . . . .
C00E C 1.0543(9) 0.7683(6) 0.8637(3) 0.0201(10) Uani 1 1 d . . . . .
C00F C 0.2049(8) 0.4471(5) 0.6111(3) 0.0207(10) Uani 1 1 d . . . . .
H00E H 0.0845 0.3653 0.6272 0.025 Uiso 1 1 calc R U . . .
H00F H 0.1274 0.5570 0.6130 0.025 Uiso 1 1 calc R U . . .
C00G C 0.6581(9) 0.3124(6) 0.8065(3) 0.0207(10) Uani 1 1 d . . . . .
C00H C 0.2536(8) 0.4113(5) 0.5228(3) 0.0198(10) Uani 1 1 d . . . . .
H00H H 0.3655 0.4980 0.5045 0.024 Uiso 1 1 calc R U . . .
C00I C 0.4452(8) 0.4423(6) 0.6751(3) 0.0187(10) Uani 1 1 d . . . . .
H00I H 0.5883 0.4085 0.6459 0.022 Uiso 1 1 calc R U . . .
C00J C 0.0056(9) 0.4095(6) 0.4653(3) 0.0283(11) Uani 1 1 d . . . . .
H00G H 0.0403 0.3866 0.4099 0.042 Uiso 1 1 calc R U . . .
H00J H -0.0758 0.5168 0.4671 0.042 Uiso 1 1 calc R U . . .
H00K H -0.1037 0.3239 0.4828 0.042 Uiso 1 1 calc R U . . .
C00K C 0.8531(9) 0.7654(6) 0.7999(3) 0.0219(10) Uani 1 1 d . . . . .
H00L H 0.8049 0.8635 0.7714 0.026 Uiso 1 1 calc R U . . .
C00L C 1.3761(10) 0.9300(7) 0.9426(3) 0.0320(13) Uani 1 1 d . . . . .
H00M H 1.5114 0.8609 0.9275 0.048 Uiso 1 1 calc R U . . .
H00N H 1.3263 0.8920 0.9943 0.048 Uiso 1 1 calc R U . . .
H00O H 1.4324 1.0444 0.9480 0.048 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 C00H 1.436(5) . ?
O001 H001 0.79(7) . ?
O002 C00G 1.235(6) . ?
O003 C00B 1.426(7) . ?
O003 H003 0.8200 . ?
O004 C00A 1.425(6) . ?
O004 H004 0.8200 . ?
O005 C00D 1.345(6) . ?
O005 H005 0.8200 . ?
O006 C00E 1.350(6) . ?
O006 C00L 1.433(6) . ?
C007 C00K 1.377(7) . ?
C007 C008 1.408(7) . ?
C007 C00A 1.527(6) . ?
C008 C00D 1.428(6) . ?
C008 C00G 1.450(7) . ?
C009 C00D 1.378(7) . ?
C009 C00E 1.396(7) . ?
C009 H009 0.9300 . ?
C00A C00I 1.526(6) . ?
C00A H00A 0.9800 . ?
C00B C00C 1.528(7) . ?
C00B H00B 0.9700 . ?
C00B H00C 0.9700 . ?
C00C C00G 1.517(6) . ?
C00C C00I 1.538(7) . ?
C00C H00D 0.9800 . ?
C00E C00K 1.403(7) . ?
C00F C00H 1.518(7) . ?
C00F C00I 1.553(5) . ?
C00F H00E 0.9700 . ?
C00F H00F 0.9700 . ?
C00H C00J 1.526(6) . ?
C00H H00H 0.9800 . ?
C00I H00I 0.9800 . ?
C00J H00G 0.9600 . ?
C00J H00J 0.9600 . ?
C00J H00K 0.9600 . ?
C00K H00L 0.9300 . ?
C00L H00M 0.9600 . ?
C00L H00N 0.9600 . ?
C00L H00O 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
C00H O001 H001 109.5 . . ?
C00B O003 H003 109.5 . . ?
C00A O004 H004 109.5 . . ?
C00D O005 H005 109.5 . . ?
C00E O006 C00L 118.6(4) . . ?
C00K C007 C008 120.6(4) . . ?
C00K C007 C00A 119.9(4) . . ?
C008 C007 C00A 119.5(4) . . ?
C007 C008 C00D 118.1(4) . . ?
C007 C008 C00G 122.6(4) . . ?
C00D C008 C00G 119.3(4) . . ?
C00D C009 C00E 119.3(4) . . ?
C00D C009 H009 120.4 . . ?
C00E C009 H009 120.4 . . ?
O004 C00A C00I 107.3(3) . . ?
O004 C00A C007 111.9(4) . . ?
C00I C00A C007 113.1(3) . . ?
O004 C00A H00A 108.1 . . ?
C00I C00A H00A 108.1 . . ?
C007 C00A H00A 108.1 . . ?
O003 C00B C00C 112.3(4) . . ?
O003 C00B H00B 109.1 . . ?
C00C C00B H00B 109.1 . . ?
O003 C00B H00C 109.1 . . ?
C00C C00B H00C 109.1 . . ?
H00B C00B H00C 107.9 . . ?
C00G C00C C00B 110.5(4) . . ?
C00G C00C C00I 111.5(4) . . ?
C00B C00C C00I 115.3(4) . . ?
C00G C00C H00D 106.3 . . ?
C00B C00C H00D 106.3 . . ?
C00I C00C H00D 106.3 . . ?
O005 C00D C009 117.3(4) . . ?
O005 C00D C008 121.5(4) . . ?
C009 C00D C008 121.2(4) . . ?
O006 C00E C009 123.7(4) . . ?
O006 C00E C00K 115.8(4) . . ?
C009 C00E C00K 120.6(4) . . ?
C00H C00F C00I 114.5(4) . . ?
C00H C00F H00E 108.6 . . ?
C00I C00F H00E 108.6 . . ?
C00H C00F H00F 108.6 . . ?
C00I C00F H00F 108.6 . . ?
H00E C00F H00F 107.6 . . ?
O002 C00G C008 121.7(4) . . ?
O002 C00G C00C 120.0(4) . . ?
C008 C00G C00C 118.2(4) . . ?
O001 C00H C00F 107.7(4) . . ?
O001 C00H C00J 110.4(3) . . ?
C00F C00H C00J 110.7(4) . . ?
O001 C00H H00H 109.3 . . ?
C00F C00H H00H 109.3 . . ?
C00J C00H H00H 109.3 . . ?
C00A C00I C00C 110.5(4) . . ?
C00A C00I C00F 110.6(3) . . ?
C00C C00I C00F 112.4(4) . . ?
C00A C00I H00I 107.7 . . ?
C00C C00I H00I 107.7 . . ?
C00F C00I H00I 107.7 . . ?
C00H C00J H00G 109.5 . . ?
C00H C00J H00J 109.5 . . ?
H00G C00J H00J 109.5 . . ?
C00H C00J H00K 109.5 . . ?
H00G C00J H00K 109.5 . . ?
H00J C00J H00K 109.5 . . ?
C007 C00K C00E 120.2(4) . . ?
C007 C00K H00L 119.9 . . ?
C00E C00K H00L 119.9 . . ?
O006 C00L H00M 109.5 . . ?
O006 C00L H00N 109.5 . . ?
H00M C00L H00N 109.5 . . ?
O006 C00L H00O 109.5 . . ?
H00M C00L H00O 109.5 . . ?
H00N C00L H00O 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
C00K C007 C008 C00D -2.9(7) . . . . ?
C00A C007 C008 C00D 179.2(4) . . . . ?
C00K C007 C008 C00G 175.8(4) . . . . ?
C00A C007 C008 C00G -2.1(7) . . . . ?
C00K C007 C00A O004 38.3(6) . . . . ?
C008 C007 C00A O004 -143.8(4) . . . . ?
C00K C007 C00A C00I 159.6(4) . . . . ?
C008 C007 C00A C00I -22.5(6) . . . . ?
O003 C00B C00C C00G -71.0(5) . . . . ?
O003 C00B C00C C00I 56.5(5) . . . . ?
C00E C009 C00D O005 179.1(4) . . . . ?
C00E C009 C00D C008 -1.7(7) . . . . ?
C007 C008 C00D O005 -177.2(4) . . . . ?
C00G C008 C00D O005 4.1(7) . . . . ?
C007 C008 C00D C009 3.6(7) . . . . ?
C00G C008 C00D C009 -175.2(4) . . . . ?
C00L O006 C00E C009 1.1(7) . . . . ?
C00L O006 C00E C00K -178.0(4) . . . . ?
C00D C009 C00E O006 180.0(4) . . . . ?
C00D C009 C00E C00K -0.9(7) . . . . ?
C007 C008 C00G O002 178.6(5) . . . . ?
C00D C008 C00G O002 -2.8(7) . . . . ?
C007 C008 C00G C00C -3.1(7) . . . . ?
C00D C008 C00G C00C 175.5(4) . . . . ?
C00B C00C C00G O002 -19.9(6) . . . . ?
C00I C00C C00G O002 -149.5(4) . . . . ?
C00B C00C C00G C008 161.7(4) . . . . ?
C00I C00C C00G C008 32.1(6) . . . . ?
C00I C00F C00H O001 56.2(4) . . . . ?
C00I C00F C00H C00J 177.0(3) . . . . ?
O004 C00A C00I C00C 174.6(3) . . . . ?
C007 C00A C00I C00C 50.8(5) . . . . ?
O004 C00A C00I C00F -60.3(5) . . . . ?
C007 C00A C00I C00F 175.9(4) . . . . ?
C00G C00C C00I C00A -55.5(5) . . . . ?
C00B C00C C00I C00A 177.5(4) . . . . ?
C00G C00C C00I C00F -179.6(4) . . . . ?
C00B C00C C00I C00F 53.4(5) . . . . ?
C00H C00F C00I C00A 113.7(4) . . . . ?
C00H C00F C00I C00C -122.2(4) . . . . ?
C008 C007 C00K C00E 0.4(7) . . . . ?
C00A C007 C00K C00E 178.3(4) . . . . ?
O006 C00E C00K C007 -179.3(4) . . . . ?
C009 C00E C00K C007 1.6(7) . . . . ?

_refine_diff_density_max         0.483
_refine_diff_density_min         -0.434
_refine_diff_density_rms         0.118

####################################################################### 
# 
# 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_20180316_0m_a
_database_code_depnum_ccdc_archive 'CCDC 1874968'
loop_
_audit_author_name
_audit_author_address
'Gang Li'
;No. 38, Dengzhou Road, Qingdao University, Qingdao 266021
China
;
_audit_update_record             
;
2018-10-24 deposited with the CCDC.	2019-04-15 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C12 H14 O5'
_chemical_formula_weight         238.23

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                   4.9905(3)
_cell_length_b                   7.7332(4)
_cell_length_c                   28.2300(14)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1089.47(10)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.452
_exptl_crystal_F_000             504
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_absorpt_coefficient_mu    0.958
_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  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            6106
_diffrn_reflns_av_unetI/netI     0.0698
_diffrn_reflns_av_R_equivalents  0.0626
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_theta_min         3.131
_diffrn_reflns_theta_max         66.570
_diffrn_reflns_theta_full        66.570
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measured_fraction_theta_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.972
_diffrn_reflns_point_group_measured_fraction_full 0.972
_reflns_number_total             1848
_reflns_number_gt                1777
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.610
_reflns_Friedel_fraction_max     0.941
_reflns_Friedel_fraction_full    0.941

_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+(0.1797P)²+0.1804P] 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 661 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.18(15)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         1848
_refine_ls_number_parameters     158
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0798
_refine_ls_R_factor_gt           0.0787
_refine_ls_wR_factor_ref         0.2083
_refine_ls_wR_factor_gt          0.2060
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_restrained_S_all      1.040
_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 0.7877(6) 0.4637(4) 0.22178(9) 0.0220(7) Uani 1 1 d . . . . .
H001 H 0.6741 0.4237 0.2039 0.033 Uiso 1 1 calc R U . . .
O002 O 0.7094(6) 0.0363(3) 0.31479(9) 0.0205(7) Uani 1 1 d . . . . .
H002 H 0.7284 0.0416 0.2860 0.031 Uiso 1 1 calc R U . . .
O003 O 0.0232(7) 0.5288(4) 0.43064(9) 0.0246(8) Uani 1 1 d . . . . .
H003 H 0.0937 0.6100 0.4167 0.037 Uiso 1 1 calc R U . . .
O004 O 0.2976(8) 0.6730(4) 0.36495(10) 0.0321(9) Uani 1 1 d . . . . .
O005 O 0.1475(7) -0.0769(4) 0.45263(10) 0.0264(8) Uani 1 1 d . . . . .
C006 C 0.3461(8) 0.3774(5) 0.38277(13) 0.0182(9) Uani 1 1 d . . . . .
C007 C 0.4003(9) 0.0690(5) 0.39597(12) 0.0192(9) Uani 1 1 d . . . . .
H007 H 0.4834 -0.0356 0.3890 0.023 Uiso 1 1 calc R U . . .
C008 C 0.6840(8) 0.2066(5) 0.33361(12) 0.0168(8) Uani 1 1 d . . . . .
H008 H 0.8551 0.2358 0.3487 0.020 Uiso 1 1 calc R U . . .
C009 C 0.6312(8) 0.3432(5) 0.29502(12) 0.0183(9) Uani 1 1 d . . . . .
H009 H 0.4585 0.3187 0.2799 0.022 Uiso 1 1 calc R U . . .
C00A C 0.4686(8) 0.2158(5) 0.37178(12) 0.0170(9) Uani 1 1 d . . . . .
C00B C 0.8512(8) 0.3392(5) 0.25736(12) 0.0201(9) Uani 1 1 d . . . . .
H00A H 1.0230 0.3663 0.2716 0.024 Uiso 1 1 calc R U . . .
H00B H 0.8623 0.2248 0.2434 0.024 Uiso 1 1 calc R U . . .
C00C C 0.0799(9) 0.2322(5) 0.44357(12) 0.0199(9) Uani 1 1 d . . . . .
H00C H -0.0463 0.2362 0.4678 0.024 Uiso 1 1 calc R U . . .
C00D C 0.2024(9) 0.0776(5) 0.43167(13) 0.0209(9) Uani 1 1 d . . . . .
C00E C 0.1477(8) 0.3815(5) 0.41891(12) 0.0183(9) Uani 1 1 d . . . . .
C00F C 0.6186(10) 0.5230(5) 0.31837(13) 0.0226(9) Uani 1 1 d . . . . .
H00D H 0.7922 0.5501 0.3319 0.027 Uiso 1 1 calc R U . . .
H00E H 0.5797 0.6090 0.2943 0.027 Uiso 1 1 calc R U . . .
C00G C 0.4093(9) 0.5329(5) 0.35647(13) 0.0213(10) Uani 1 1 d . . . . .
C00H C -0.0454(10) -0.0767(6) 0.49012(14) 0.0274(10) Uani 1 1 d . . . . .
H00F H -0.2127 -0.0323 0.4785 0.041 Uiso 1 1 calc R U . . .
H00G H 0.0176 -0.0049 0.5155 0.041 Uiso 1 1 calc R U . . .
H00H H -0.0706 -0.1926 0.5014 0.041 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 C00B 1.427(4) . ?
O001 H001 0.8200 . ?
O002 C008 1.426(4) . ?
O002 H002 0.8200 . ?
O003 C00E 1.339(5) . ?
O003 H003 0.8200 . ?
O004 C00G 1.242(5) . ?
O005 C00D 1.361(5) . ?
O005 C00H 1.431(5) . ?
C006 C00E 1.422(6) . ?
C006 C00A 1.426(5) . ?
C006 C00G 1.448(5) . ?
C007 C00A 1.368(6) . ?
C007 C00D 1.412(6) . ?
C007 H007 0.9300 . ?
C008 C00A 1.524(5) . ?
C008 C009 1.540(4) . ?
C008 H008 0.9800 . ?
C009 C00B 1.529(5) . ?
C009 C00F 1.540(5) . ?
C009 H009 0.9800 . ?
C00B H00A 0.9700 . ?
C00B H00B 0.9700 . ?
C00C C00D 1.384(6) . ?
C00C C00E 1.390(5) . ?
C00C H00C 0.9300 . ?
C00F C00G 1.501(5) . ?
C00F H00D 0.9700 . ?
C00F H00E 0.9700 . ?
C00H H00F 0.9600 . ?
C00H H00G 0.9600 . ?
C00H 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 . . ?
C008 O002 H002 109.5 . . ?
C00E O003 H003 109.5 . . ?
C00D O005 C00H 117.1(3) . . ?
C00E C006 C00A 118.3(3) . . ?
C00E C006 C00G 120.1(3) . . ?
C00A C006 C00G 121.5(3) . . ?
C00A C007 C00D 119.4(4) . . ?
C00A C007 H007 120.3 . . ?
C00D C007 H007 120.3 . . ?
O002 C008 C00A 111.7(3) . . ?
O002 C008 C009 112.7(3) . . ?
C00A C008 C009 110.3(3) . . ?
O002 C008 H008 107.3 . . ?
C00A C008 H008 107.3 . . ?
C009 C008 H008 107.3 . . ?
C00B C009 C00F 110.2(3) . . ?
C00B C009 C008 110.8(3) . . ?
C00F C009 C008 108.9(3) . . ?
C00B C009 H009 109.0 . . ?
C00F C009 H009 109.0 . . ?
C008 C009 H009 109.0 . . ?
C007 C00A C006 120.8(3) . . ?
C007 C00A C008 119.3(3) . . ?
C006 C00A C008 119.8(3) . . ?
O001 C00B C009 108.4(3) . . ?
O001 C00B H00A 110.0 . . ?
C009 C00B H00A 110.0 . . ?
O001 C00B H00B 110.0 . . ?
C009 C00B H00B 110.0 . . ?
H00A C00B H00B 108.4 . . ?
C00D C00C C00E 119.2(4) . . ?
C00D C00C H00C 120.4 . . ?
C00E C00C H00C 120.4 . . ?
O005 C00D C00C 124.3(3) . . ?
O005 C00D C007 114.2(4) . . ?
C00C C00D C007 121.5(4) . . ?
O003 C00E C00C 118.0(3) . . ?
O003 C00E C006 121.3(3) . . ?
C00C C00E C006 120.7(3) . . ?
C00G C00F C009 112.4(3) . . ?
C00G C00F H00D 109.1 . . ?
C009 C00F H00D 109.1 . . ?
C00G C00F H00E 109.1 . . ?
C009 C00F H00E 109.1 . . ?
H00D C00F H00E 107.9 . . ?
O004 C00G C006 121.9(4) . . ?
O004 C00G C00F 119.7(3) . . ?
C006 C00G C00F 118.5(3) . . ?
O005 C00H H00F 109.5 . . ?
O005 C00H H00G 109.5 . . ?
H00F C00H H00G 109.5 . . ?
O005 C00H H00H 109.5 . . ?
H00F C00H H00H 109.5 . . ?
H00G C00H 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 C008 C009 C00B -56.3(4) . . . . ?
C00A C008 C009 C00B 178.1(3) . . . . ?
O002 C008 C009 C00F -177.7(3) . . . . ?
C00A C008 C009 C00F 56.8(4) . . . . ?
C00D C007 C00A C006 1.1(6) . . . . ?
C00D C007 C00A C008 179.4(3) . . . . ?
C00E C006 C00A C007 -1.1(6) . . . . ?
C00G C006 C00A C007 -177.9(3) . . . . ?
C00E C006 C00A C008 -179.4(3) . . . . ?
C00G C006 C00A C008 3.9(6) . . . . ?
O002 C008 C00A C007 24.1(5) . . . . ?
C009 C008 C00A C007 150.2(3) . . . . ?
O002 C008 C00A C006 -157.6(3) . . . . ?
C009 C008 C00A C006 -31.5(4) . . . . ?
C00F C009 C00B O001 -61.4(4) . . . . ?
C008 C009 C00B O001 178.0(3) . . . . ?
C00H O005 C00D C00C -1.5(6) . . . . ?
C00H O005 C00D C007 178.2(3) . . . . ?
C00E C00C C00D O005 -178.5(4) . . . . ?
C00E C00C C00D C007 1.8(6) . . . . ?
C00A C007 C00D O005 178.8(4) . . . . ?
C00A C007 C00D C00C -1.5(6) . . . . ?
C00D C00C C00E O003 179.0(3) . . . . ?
C00D C00C C00E C006 -1.8(6) . . . . ?
C00A C006 C00E O003 -179.4(4) . . . . ?
C00G C006 C00E O003 -2.6(5) . . . . ?
C00A C006 C00E C00C 1.4(5) . . . . ?
C00G C006 C00E C00C 178.2(4) . . . . ?
C00B C009 C00F C00G -178.8(3) . . . . ?
C008 C009 C00F C00G -57.0(5) . . . . ?
C00E C006 C00G O004 1.2(6) . . . . ?
C00A C006 C00G O004 177.9(4) . . . . ?
C00E C006 C00G C00F -179.6(3) . . . . ?
C00A C006 C00G C00F -2.9(6) . . . . ?
C009 C00F C00G O004 -150.6(4) . . . . ?
C009 C00F C00G C006 30.1(5) . . . . ?

_refine_diff_density_max         0.480
_refine_diff_density_min         -0.461
_refine_diff_density_rms         0.124

####################################################################### 
# 
# 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_20170902_0m_a
_database_code_depnum_ccdc_archive 'CCDC 1874969'
loop_
_audit_author_name
_audit_author_address
'Gang Li'
;No. 38, Dengzhou Road, Qingdao University, Qingdao 266021
China
;
_audit_update_record             
;
2018-10-24 deposited with the CCDC.	2019-04-15 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C14 H16 O5'
_chemical_formula_weight         264.27

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                   9.6371(4)
_cell_length_b                   11.5399(5)
_cell_length_c                   11.7536(5)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1307.13(10)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.343
_exptl_crystal_F_000             560
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_absorpt_coefficient_mu    0.853
_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  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            9795
_diffrn_reflns_av_unetI/netI     0.2108
_diffrn_reflns_av_R_equivalents  0.3617
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         5.372
_diffrn_reflns_theta_max         68.372
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             2389
_reflns_number_gt                2002
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.719
_reflns_Friedel_fraction_max     0.996
_reflns_Friedel_fraction_full    1.000

_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+(0.1217P)²+0.3742P] 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 552 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.1(6)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         2389
_refine_ls_number_parameters     176
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0970
_refine_ls_R_factor_gt           0.0852
_refine_ls_wR_factor_ref         0.2512
_refine_ls_wR_factor_gt          0.2299
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_restrained_S_all      1.047
_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 -0.3393(4) -0.7403(4) -0.9267(3) 0.0437(10) Uani 1 1 d . . . . .
H001 H -0.3451 -0.8040 -0.8961 0.066 Uiso 1 1 calc R U . . .
O002 O -0.2362(5) -0.5817(4) -0.5006(3) 0.0494(11) Uani 1 1 d . . . . .
O003 O 0.1696(5) -0.8179(5) -0.8527(3) 0.0582(13) Uani 1 1 d . . . . .
H003 H 0.1564 -0.8086 -0.9210 0.087 Uiso 1 1 calc R U . . .
O004 O -0.0020(5) -0.6904(5) -0.5028(3) 0.0585(13) Uani 1 1 d . . . . .
H004 H -0.0741 -0.6700 -0.4716 0.088 Uiso 1 1 calc R U . . .
O005 O -0.5947(5) -0.4590(4) -0.6597(4) 0.0611(13) Uani 1 1 d . . . . .
C006 C -0.3009(5) -0.6546(4) -0.8431(4) 0.0336(11) Uani 1 1 d . . . . .
H006 H -0.2852 -0.5816 -0.8838 0.040 Uiso 1 1 calc R U . . .
C007 C -0.1468(5) -0.6658(4) -0.6681(4) 0.0325(11) Uani 1 1 d . . . . .
C008 C -0.1654(5) -0.6870(4) -0.7855(4) 0.0319(11) Uani 1 1 d . . . . .
C009 C -0.2486(6) -0.5987(5) -0.6049(4) 0.0385(12) Uani 1 1 d . . . . .
C00A C -0.0255(6) -0.7061(5) -0.6160(4) 0.0404(13) Uani 1 1 d . . . . .
C00B C -0.4183(5) -0.6341(5) -0.7600(4) 0.0358(12) Uani 1 1 d . . . . .
H00B H -0.4416 -0.7074 -0.7225 0.043 Uiso 1 1 calc R U . . .
C00C C -0.3673(6) -0.5468(5) -0.6698(4) 0.0398(12) Uani 1 1 d . . . . .
H00C H -0.3319 -0.4787 -0.7103 0.048 Uiso 1 1 calc R U . . .
C00D C -0.0613(5) -0.7374(5) -0.8475(4) 0.0354(11) Uani 1 1 d . . . . .
H00D H -0.0723 -0.7486 -0.9254 0.043 Uiso 1 1 calc R U . . .
C00E C 0.0624(5) -0.7723(5) -0.7937(5) 0.0408(13) Uani 1 1 d . . . . .
C00F C 0.0782(6) -0.7599(6) -0.6777(5) 0.0449(13) Uani 1 1 d . . . . .
H00F H 0.1574 -0.7875 -0.6415 0.054 Uiso 1 1 calc R U . . .
C00G C -0.5470(6) -0.5865(5) -0.8175(6) 0.0477(14) Uani 1 1 d . . . . .
H00A H -0.5198 -0.5236 -0.8674 0.057 Uiso 1 1 calc R U . . .
H00E H -0.5872 -0.6470 -0.8644 0.057 Uiso 1 1 calc R U . . .
C00H C -0.6568(7) -0.5425(6) -0.7366(7) 0.0563(16) Uani 1 1 d . . . . .
H00H H -0.6908 -0.6081 -0.6915 0.068 Uiso 1 1 calc R U . . .
C00I C -0.4850(7) -0.5066(7) -0.5937(6) 0.0556(16) Uani 1 1 d . . . . .
H00G H -0.5195 -0.5717 -0.5497 0.067 Uiso 1 1 calc R U . . .
H00I H -0.4508 -0.4486 -0.5409 0.067 Uiso 1 1 calc R U . . .
C00J C -0.7785(9) -0.4866(7) -0.7941(10) 0.082(3) Uani 1 1 d . . . . .
H00J H -0.8227 -0.5417 -0.8434 0.123 Uiso 1 1 calc R U . . .
H00K H -0.7472 -0.4215 -0.8380 0.123 Uiso 1 1 calc R U . . .
H00L H -0.8436 -0.4607 -0.7377 0.123 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 C006 1.442(6) . ?
O001 H001 0.8200 . ?
O002 C009 1.246(6) . ?
O003 C00E 1.351(7) . ?
O003 H003 0.8200 . ?
O004 C00A 1.362(6) . ?
O004 H004 0.8200 . ?
O005 C00I 1.423(8) . ?
O005 C00H 1.450(8) . ?
C006 C00B 1.514(7) . ?
C006 C008 1.517(6) . ?
C006 H006 0.9800 . ?
C007 C00A 1.400(8) . ?
C007 C008 1.413(6) . ?
C007 C009 1.454(7) . ?
C008 C00D 1.370(7) . ?
C009 C00C 1.500(8) . ?
C00A C00F 1.382(9) . ?
C00B C00G 1.515(7) . ?
C00B C00C 1.543(7) . ?
C00B H00B 0.9800 . ?
C00C C00I 1.517(8) . ?
C00C H00C 0.9800 . ?
C00D C00E 1.409(7) . ?
C00D H00D 0.9300 . ?
C00E C00F 1.380(8) . ?
C00F H00F 0.9300 . ?
C00G C00H 1.510(9) . ?
C00G H00A 0.9700 . ?
C00G H00E 0.9700 . ?
C00H C00J 1.500(10) . ?
C00H H00H 0.9800 . ?
C00I H00G 0.9700 . ?
C00I H00I 0.9700 . ?
C00J H00J 0.9600 . ?
C00J H00K 0.9600 . ?
C00J H00L 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
C006 O001 H001 109.5 . . ?
C00E O003 H003 109.5 . . ?
C00A O004 H004 109.5 . . ?
C00I O005 C00H 113.0(5) . . ?
O001 C006 C00B 110.7(4) . . ?
O001 C006 C008 110.9(4) . . ?
C00B C006 C008 113.2(4) . . ?
O001 C006 H006 107.2 . . ?
C00B C006 H006 107.2 . . ?
C008 C006 H006 107.2 . . ?
C00A C007 C008 118.4(5) . . ?
C00A C007 C009 121.1(4) . . ?
C008 C007 C009 120.4(5) . . ?
C00D C008 C007 120.0(5) . . ?
C00D C008 C006 119.8(4) . . ?
C007 C008 C006 120.1(4) . . ?
O002 C009 C007 121.4(5) . . ?
O002 C009 C00C 120.7(5) . . ?
C007 C009 C00C 117.8(4) . . ?
O004 C00A C00F 116.9(5) . . ?
O004 C00A C007 121.5(5) . . ?
C00F C00A C007 121.6(4) . . ?
C006 C00B C00G 112.4(4) . . ?
C006 C00B C00C 107.9(4) . . ?
C00G C00B C00C 109.3(5) . . ?
C006 C00B H00B 109.1 . . ?
C00G C00B H00B 109.1 . . ?
C00C C00B H00B 109.1 . . ?
C009 C00C C00I 113.0(4) . . ?
C009 C00C C00B 109.4(4) . . ?
C00I C00C C00B 111.5(5) . . ?
C009 C00C H00C 107.5 . . ?
C00I C00C H00C 107.5 . . ?
C00B C00C H00C 107.5 . . ?
C008 C00D C00E 120.2(4) . . ?
C008 C00D H00D 119.9 . . ?
C00E C00D H00D 119.9 . . ?
O003 C00E C00F 117.6(5) . . ?
O003 C00E C00D 121.9(5) . . ?
C00F C00E C00D 120.5(5) . . ?
C00E C00F C00A 119.1(5) . . ?
C00E C00F H00F 120.5 . . ?
C00A C00F H00F 120.5 . . ?
C00H C00G C00B 114.5(5) . . ?
C00H C00G H00A 108.6 . . ?
C00B C00G H00A 108.6 . . ?
C00H C00G H00E 108.6 . . ?
C00B C00G H00E 108.6 . . ?
H00A C00G H00E 107.6 . . ?
O005 C00H C00J 108.5(5) . . ?
O005 C00H C00G 109.0(5) . . ?
C00J C00H C00G 114.2(7) . . ?
O005 C00H H00H 108.3 . . ?
C00J C00H H00H 108.3 . . ?
C00G C00H H00H 108.3 . . ?
O005 C00I C00C 110.6(5) . . ?
O005 C00I H00G 109.5 . . ?
C00C C00I H00G 109.5 . . ?
O005 C00I H00I 109.5 . . ?
C00C C00I H00I 109.5 . . ?
H00G C00I H00I 108.1 . . ?
C00H C00J H00J 109.5 . . ?
C00H C00J H00K 109.5 . . ?
H00J C00J H00K 109.5 . . ?
C00H C00J H00L 109.5 . . ?
H00J C00J H00L 109.5 . . ?
H00K C00J H00L 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
C00A C007 C008 C00D -5.2(7) . . . . ?
C009 C007 C008 C00D 171.8(5) . . . . ?
C00A C007 C008 C006 174.4(5) . . . . ?
C009 C007 C008 C006 -8.5(7) . . . . ?
O001 C006 C008 C00D 37.6(6) . . . . ?
C00B C006 C008 C00D 162.7(5) . . . . ?
O001 C006 C008 C007 -142.1(4) . . . . ?
C00B C006 C008 C007 -16.9(6) . . . . ?
C00A C007 C009 O002 -5.1(8) . . . . ?
C008 C007 C009 O002 178.0(5) . . . . ?
C00A C007 C009 C00C 172.9(5) . . . . ?
C008 C007 C009 C00C -4.0(7) . . . . ?
C008 C007 C00A O004 -178.8(5) . . . . ?
C009 C007 C00A O004 4.1(8) . . . . ?
C008 C007 C00A C00F 3.5(8) . . . . ?
C009 C007 C00A C00F -173.6(5) . . . . ?
O001 C006 C00B C00G -62.4(5) . . . . ?
C008 C006 C00B C00G 172.4(4) . . . . ?
O001 C006 C00B C00C 177.0(4) . . . . ?
C008 C006 C00B C00C 51.8(6) . . . . ?
O002 C009 C00C C00I -17.1(8) . . . . ?
C007 C009 C00C C00I 164.9(5) . . . . ?
O002 C009 C00C C00B -142.0(5) . . . . ?
C007 C009 C00C C00B 40.0(6) . . . . ?
C006 C00B C00C C009 -63.1(5) . . . . ?
C00G C00B C00C C009 174.4(4) . . . . ?
C006 C00B C00C C00I 171.1(5) . . . . ?
C00G C00B C00C C00I 48.6(6) . . . . ?
C007 C008 C00D C00E 2.4(8) . . . . ?
C006 C008 C00D C00E -177.3(5) . . . . ?
C008 C00D C00E O003 -177.3(5) . . . . ?
C008 C00D C00E C00F 2.4(9) . . . . ?
O003 C00E C00F C00A 175.5(5) . . . . ?
C00D C00E C00F C00A -4.1(9) . . . . ?
O004 C00A C00F C00E -176.6(6) . . . . ?
C007 C00A C00F C00E 1.2(9) . . . . ?
C006 C00B C00G C00H -168.5(5) . . . . ?
C00C C00B C00G C00H -48.8(6) . . . . ?
C00I O005 C00H C00J 175.1(7) . . . . ?
C00I O005 C00H C00G -60.1(7) . . . . ?
C00B C00G C00H O005 53.7(7) . . . . ?
C00B C00G C00H C00J 175.2(6) . . . . ?
C00H O005 C00I C00C 62.4(7) . . . . ?
C009 C00C C00I O005 -179.6(5) . . . . ?
C00B C00C C00I O005 -55.9(7) . . . . ?

_refine_diff_density_max         0.297
_refine_diff_density_min         -0.450
_refine_diff_density_rms         0.099

####################################################################### 
# 
# 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_20171002_0m_a
_database_code_depnum_ccdc_archive 'CCDC 1874970'
loop_
_audit_author_name
_audit_author_address
'Gang Li'
;No. 38, Dengzhou Road, Qingdao University, Qingdao 266021
China
;
_audit_update_record             
;
2018-10-24 deposited with the CCDC.	2019-04-15 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C1.67 H1.11 O0.56'
_chemical_formula_weight         30.03

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                   3.8904(3)
_cell_length_b                   17.2043(11)
_cell_length_c                   18.0371(12)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1207.25(15)
_cell_formula_units_Z            36
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.487
_exptl_crystal_F_000             560
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_absorpt_coefficient_mu    0.953
_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  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            14865
_diffrn_reflns_av_unetI/netI     0.0354
_diffrn_reflns_av_R_equivalents  0.0679
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         3.550
_diffrn_reflns_theta_max         66.594
_diffrn_reflns_theta_full        66.594
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             2139
_reflns_number_gt                1806
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.637
_reflns_Friedel_fraction_max     1.000
_reflns_Friedel_fraction_full    1.000

_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+(0.0616P)²+0.0289P] 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 624 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.24(17)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         2139
_refine_ls_number_parameters     185
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0508
_refine_ls_R_factor_gt           0.0402
_refine_ls_wR_factor_ref         0.1053
_refine_ls_wR_factor_gt          0.0987
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_restrained_S_all      1.061
_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 0.4743(6) 0.27156(11) 0.38000(11) 0.0395(5) Uani 1 1 d . . . . .
O002 O -0.1318(6) 0.54461(12) 0.37639(12) 0.0498(6) Uani 1 1 d . . . . .
O003 O 0.1770(8) 0.34121(13) 0.09165(12) 0.0536(7) Uani 1 1 d . . . . .
H003 H 0.2498 0.3064 0.0649 0.080 Uiso 1 1 calc R U . . .
O004 O -0.1082(8) 0.47106(14) 0.12904(12) 0.0582(7) Uani 1 1 d . . . . .
H004 H -0.0516 0.4359 0.1009 0.087 Uiso 1 1 calc R U . . .
O005 O 0.4708(8) 0.21161(15) 0.05828(13) 0.0652(8) Uani 1 1 d . . . . .
C006 C 0.1517(8) 0.38076(16) 0.21741(16) 0.0351(7) Uani 1 1 d . . . . .
C007 C 0.3924(8) 0.29593(16) 0.30969(15) 0.0340(6) Uani 1 1 d . . . . .
C008 C 0.2231(7) 0.36668(15) 0.29383(16) 0.0326(6) Uani 1 1 d . . . . .
C009 C 0.1323(8) 0.42015(16) 0.34910(16) 0.0353(6) Uani 1 1 d . . . . .
H009 H 0.1823 0.4102 0.3986 0.042 Uiso 1 1 calc R U . . .
C00A C -0.0212(9) 0.45174(17) 0.19978(17) 0.0386(7) Uani 1 1 d . . . . .
C00B C 0.4239(8) 0.25671(17) 0.18149(16) 0.0382(7) Uani 1 1 d . . . . .
C00C C -0.0328(8) 0.48792(16) 0.32848(16) 0.0371(7) Uani 1 1 d . . . . .
C00D C 0.2540(8) 0.32490(17) 0.16341(16) 0.0366(7) Uani 1 1 d . . . . .
C00E C 0.4921(8) 0.24230(16) 0.25812(17) 0.0359(6) Uani 1 1 d . . . . .
C00F C 0.6469(8) 0.18040(17) 0.29942(18) 0.0428(7) Uani 1 1 d . . . . .
H00F H 0.7417 0.1351 0.2801 0.051 Uiso 1 1 calc R U . . .
C00G C -0.1116(8) 0.50284(16) 0.25436(16) 0.0400(7) Uani 1 1 d . . . . .
H00G H -0.2274 0.5483 0.2419 0.048 Uiso 1 1 calc R U . . .
C00H C 0.6296(8) 0.20002(18) 0.37091(18) 0.0435(7) Uani 1 1 d . . . . .
C00I C 0.5299(9) 0.2031(2) 0.12495(18) 0.0484(8) Uani 1 1 d . . . . .
H00I H 0.6510 0.1591 0.1396 0.058 Uiso 1 1 calc R U . . .
C00J C -0.0446(11) 0.5356(2) 0.45277(19) 0.0561(9) Uani 1 1 d . . . . .
H00A H -0.1580 0.4905 0.4723 0.084 Uiso 1 1 calc R U . . .
H00B H -0.1169 0.5808 0.4798 0.084 Uiso 1 1 calc R U . . .
H00C H 0.1996 0.5295 0.4575 0.084 Uiso 1 1 calc R U . . .
C00K C 0.7407(11) 0.1604(2) 0.4401(2) 0.0609(10) Uani 1 1 d . . . . .
H00D H 0.8378 0.1107 0.4280 0.091 Uiso 1 1 calc R U . . .
H00E H 0.5460 0.1533 0.4721 0.091 Uiso 1 1 calc R U . . .
H00H H 0.9101 0.1916 0.4648 0.091 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 C007 1.373(3) . ?
O001 C00H 1.381(4) . ?
O002 C00C 1.359(3) . ?
O002 C00J 1.427(4) . ?
O003 C00D 1.358(4) . ?
O003 H003 0.8200 . ?
O004 C00A 1.361(4) . ?
O004 H004 0.8200 . ?
O005 C00I 1.233(4) . ?
C006 C00D 1.425(4) . ?
C006 C008 1.427(4) . ?
C006 C00A 1.430(4) . ?
C007 C00E 1.366(4) . ?
C007 C008 1.413(4) . ?
C008 C009 1.402(4) . ?
C009 C00C 1.382(4) . ?
C009 H009 0.9300 . ?
C00A C00G 1.366(4) . ?
C00B C00D 1.385(4) . ?
C00B C00E 1.429(4) . ?
C00B C00I 1.436(4) . ?
C00C C00G 1.395(4) . ?
C00E C00F 1.432(4) . ?
C00F C00H 1.335(4) . ?
C00F H00F 0.9300 . ?
C00G H00G 0.9300 . ?
C00H C00K 1.486(5) . ?
C00I H00I 0.9300 . ?
C00J H00A 0.9600 . ?
C00J H00B 0.9600 . ?
C00J H00C 0.9600 . ?
C00K H00D 0.9600 . ?
C00K H00E 0.9600 . ?
C00K 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
C007 O001 C00H 105.3(2) . . ?
C00C O002 C00J 117.9(3) . . ?
C00D O003 H003 109.5 . . ?
C00A O004 H004 109.5 . . ?
C00D C006 C008 119.4(3) . . ?
C00D C006 C00A 123.7(3) . . ?
C008 C006 C00A 116.8(3) . . ?
C00E C007 O001 110.9(3) . . ?
C00E C007 C008 125.2(3) . . ?
O001 C007 C008 123.9(2) . . ?
C009 C008 C007 122.6(3) . . ?
C009 C008 C006 121.8(3) . . ?
C007 C008 C006 115.6(2) . . ?
C00C C009 C008 118.6(3) . . ?
C00C C009 H009 120.7 . . ?
C008 C009 H009 120.7 . . ?
O004 C00A C00G 117.0(3) . . ?
O004 C00A C006 122.3(3) . . ?
C00G C00A C006 120.7(3) . . ?
C00D C00B C00E 117.6(3) . . ?
C00D C00B C00I 120.9(3) . . ?
C00E C00B C00I 121.5(3) . . ?
O002 C00C C009 124.5(3) . . ?
O002 C00C C00G 114.5(3) . . ?
C009 C00C C00G 121.0(3) . . ?
O003 C00D C00B 120.3(3) . . ?
O003 C00D C006 116.8(3) . . ?
C00B C00D C006 122.9(3) . . ?
C007 C00E C00B 119.2(3) . . ?
C007 C00E C00F 105.5(3) . . ?
C00B C00E C00F 135.2(3) . . ?
C00H C00F C00E 107.0(3) . . ?
C00H C00F H00F 126.5 . . ?
C00E C00F H00F 126.5 . . ?
C00A C00G C00C 121.0(3) . . ?
C00A C00G H00G 119.5 . . ?
C00C C00G H00G 119.5 . . ?
C00F C00H O001 111.2(3) . . ?
C00F C00H C00K 132.9(3) . . ?
O001 C00H C00K 115.9(3) . . ?
O005 C00I C00B 124.3(3) . . ?
O005 C00I H00I 117.9 . . ?
C00B C00I H00I 117.9 . . ?
O002 C00J H00A 109.5 . . ?
O002 C00J H00B 109.5 . . ?
H00A C00J H00B 109.5 . . ?
O002 C00J H00C 109.5 . . ?
H00A C00J H00C 109.5 . . ?
H00B C00J H00C 109.5 . . ?
C00H C00K H00D 109.5 . . ?
C00H C00K H00E 109.5 . . ?
H00D C00K H00E 109.5 . . ?
C00H C00K H00H 109.5 . . ?
H00D C00K H00H 109.5 . . ?
H00E C00K 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
C00H O001 C007 C00E -0.1(3) . . . . ?
C00H O001 C007 C008 179.0(3) . . . . ?
C00E C007 C008 C009 -178.9(3) . . . . ?
O001 C007 C008 C009 2.2(4) . . . . ?
C00E C007 C008 C006 0.7(4) . . . . ?
O001 C007 C008 C006 -178.3(3) . . . . ?
C00D C006 C008 C009 179.1(3) . . . . ?
C00A C006 C008 C009 -0.8(4) . . . . ?
C00D C006 C008 C007 -0.4(4) . . . . ?
C00A C006 C008 C007 179.7(3) . . . . ?
C007 C008 C009 C00C 180.0(3) . . . . ?
C006 C008 C009 C00C 0.5(4) . . . . ?
C00D C006 C00A O004 1.2(5) . . . . ?
C008 C006 C00A O004 -178.9(3) . . . . ?
C00D C006 C00A C00G -179.9(3) . . . . ?
C008 C006 C00A C00G 0.0(4) . . . . ?
C00J O002 C00C C009 3.3(5) . . . . ?
C00J O002 C00C C00G -176.8(3) . . . . ?
C008 C009 C00C O002 -179.4(3) . . . . ?
C008 C009 C00C C00G 0.6(4) . . . . ?
C00E C00B C00D O003 -178.9(3) . . . . ?
C00I C00B C00D O003 1.7(4) . . . . ?
C00E C00B C00D C006 1.0(4) . . . . ?
C00I C00B C00D C006 -178.4(3) . . . . ?
C008 C006 C00D O003 179.5(3) . . . . ?
C00A C006 C00D O003 -0.6(4) . . . . ?
C008 C006 C00D C00B -0.4(4) . . . . ?
C00A C006 C00D C00B 179.5(3) . . . . ?
O001 C007 C00E C00B 179.0(3) . . . . ?
C008 C007 C00E C00B -0.1(5) . . . . ?
O001 C007 C00E C00F -0.1(3) . . . . ?
C008 C007 C00E C00F -179.2(3) . . . . ?
C00D C00B C00E C007 -0.8(4) . . . . ?
C00I C00B C00E C007 178.6(3) . . . . ?
C00D C00B C00E C00F 178.0(3) . . . . ?
C00I C00B C00E C00F -2.6(5) . . . . ?
C007 C00E C00F C00H 0.3(4) . . . . ?
C00B C00E C00F C00H -178.6(3) . . . . ?
O004 C00A C00G C00C -180.0(3) . . . . ?
C006 C00A C00G C00C 1.1(5) . . . . ?
O002 C00C C00G C00A 178.6(3) . . . . ?
C009 C00C C00G C00A -1.4(5) . . . . ?
C00E C00F C00H O001 -0.4(4) . . . . ?
C00E C00F C00H C00K 179.3(4) . . . . ?
C007 O001 C00H C00F 0.3(3) . . . . ?
C007 O001 C00H C00K -179.4(3) . . . . ?
C00D C00B C00I O005 -2.5(5) . . . . ?
C00E C00B C00I O005 178.2(3) . . . . ?

_refine_diff_density_max         0.146
_refine_diff_density_min         -0.267
_refine_diff_density_rms         0.048

