# Electronic Supplementary Material (ESI) for Green Chemistry.
# This journal is © The Royal Society of Chemistry 2022

####################################################################### 
# 
# 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_Anirban_1_0m_a
_database_code_depnum_ccdc_archive 'CCDC 2127292'
loop_
_audit_author_name
_audit_author_address
'Folkert de Vries'
;University of Groningen
Netherlands
;
_audit_update_record             
;
2021-12-08 deposited with the CCDC.	2022-03-11 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/1
_shelx_SHELXL_version_number     2018/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C32 H44 O6'
_chemical_formula_sum            'C32 H44 O6'
_chemical_formula_weight         524.67

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           5
_space_group_name_H-M_alt        'C 2'
_space_group_name_Hall           'C 2y'

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

_cell_length_a                   23.8610(8)
_cell_length_b                   6.1612(2)
_cell_length_c                   10.0136(3)
_cell_angle_alpha                90
_cell_angle_beta                 95.846(2)
_cell_angle_gamma                90
_cell_volume                     1464.47(8)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    8100
_cell_measurement_theta_min      3.72
_cell_measurement_theta_max      72.36

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.190
_exptl_crystal_F_000             568
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.465
_exptl_crystal_size_mid          0.291
_exptl_crystal_size_min          0.109
_exptl_absorpt_coefficient_mu    0.646
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6556
_exptl_absorpt_correction_T_max  0.7536
_exptl_absorpt_process_details   'SADABS 2014/5'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(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            11160
_diffrn_reflns_av_unetI/netI     0.0332
_diffrn_reflns_av_R_equivalents  0.0386
_diffrn_reflns_limit_h_min       -29
_diffrn_reflns_limit_h_max       29
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         3.724
_diffrn_reflns_theta_max         72.360
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measured_fraction_theta_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.965
_diffrn_reflns_point_group_measured_fraction_full 0.977
_reflns_number_total             2820
_reflns_number_gt                2661
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.774
_reflns_Friedel_fraction_max     0.933
_reflns_Friedel_fraction_full    0.959

_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 APEX3'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/1 (Sheldrick, 2018)'
_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)+(0.0299P)²+0.7920P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_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 1089 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.07(9)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         2820
_refine_ls_number_parameters     177
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0386
_refine_ls_R_factor_gt           0.0353
_refine_ls_wR_factor_ref         0.0842
_refine_ls_wR_factor_gt          0.0823
_refine_ls_goodness_of_fit_ref   1.160
_refine_ls_restrained_S_all      1.160
_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
C1 C 0.49165(9) 0.4633(4) 0.4338(2) 0.0150(4) Uani 1 1 d . . . . .
C2 C 0.52954(9) 0.4135(4) 0.3228(2) 0.0158(5) Uani 1 1 d . . . . .
H2 H 0.566289 0.351552 0.362248 0.019 Uiso 1 1 calc R U . . .
C3 C 0.49408(9) 0.2370(4) 0.2414(2) 0.0172(5) Uani 1 1 d . . . . .
H3A H 0.501484 0.237632 0.145938 0.021 Uiso 1 1 calc R U . . .
H3B H 0.502090 0.090621 0.279418 0.021 Uiso 1 1 calc R U . . .
C4 C 0.43418(9) 0.3058(4) 0.2571(2) 0.0161(5) Uani 1 1 d . . . . .
C5 C 0.43341(9) 0.4414(4) 0.3686(2) 0.0153(5) Uani 1 1 d . . . . .
C6 C 0.38237(9) 0.5347(4) 0.3959(2) 0.0152(5) Uani 1 1 d . . . . .
C7 C 0.33314(9) 0.4832(4) 0.3152(2) 0.0178(5) Uani 1 1 d . . . . .
C8 C 0.33428(10) 0.3336(4) 0.2104(2) 0.0187(5) Uani 1 1 d . . . . .
C9 C 0.38526(10) 0.2461(4) 0.1789(2) 0.0175(5) Uani 1 1 d . . . . .
H9 H 0.386429 0.148217 0.105943 0.021 Uiso 1 1 calc R U . . .
C10 C 0.53952(9) 0.6103(4) 0.2346(2) 0.0173(5) Uani 1 1 d . . . . .
H10A H 0.556215 0.728289 0.292828 0.021 Uiso 1 1 calc R U . . .
H10B H 0.502622 0.662232 0.192392 0.021 Uiso 1 1 calc R U . . .
C11 C 0.57813(10) 0.5678(4) 0.1231(2) 0.0217(5) Uani 1 1 d . . . . .
H11 H 0.558409 0.464435 0.057134 0.026 Uiso 1 1 calc R U . . .
C12 C 0.58857(12) 0.7783(5) 0.0496(3) 0.0320(6) Uani 1 1 d . . . . .
H12A H 0.609189 0.746650 -0.027953 0.048 Uiso 1 1 calc R U . . .
H12B H 0.610829 0.877275 0.110526 0.048 Uiso 1 1 calc R U . . .
H12C H 0.552417 0.846308 0.018851 0.048 Uiso 1 1 calc R U . . .
C13 C 0.63397(11) 0.4663(5) 0.1776(3) 0.0329(6) Uani 1 1 d . . . . .
H13A H 0.658875 0.457700 0.105816 0.049 Uiso 1 1 calc R U . . .
H13B H 0.627287 0.320104 0.211141 0.049 Uiso 1 1 calc R U . . .
H13C H 0.651700 0.555832 0.251065 0.049 Uiso 1 1 calc R U . . .
O1 O 0.37941(6) 0.6778(2) 0.50078(14) 0.0173(4) Uani 1 1 d . . . . .
C14 C 0.39256(11) 0.8951(4) 0.4650(2) 0.0252(6) Uani 1 1 d . . . . .
H14A H 0.364668 0.945956 0.393236 0.038 Uiso 1 1 calc R U . . .
H14B H 0.430149 0.898797 0.433739 0.038 Uiso 1 1 calc R U . . .
H14C H 0.391878 0.989578 0.543577 0.038 Uiso 1 1 calc R U . . .
O2 O 0.28372(6) 0.5900(3) 0.33437(16) 0.0218(4) Uani 1 1 d . . . . .
C15 C 0.24597(11) 0.4656(5) 0.4058(3) 0.0334(6) Uani 1 1 d . . . . .
H15A H 0.210610 0.545550 0.408640 0.050 Uiso 1 1 calc R U . . .
H15B H 0.263100 0.439470 0.497532 0.050 Uiso 1 1 calc R U . . .
H15C H 0.238314 0.326387 0.360185 0.050 Uiso 1 1 calc R U . . .
O3 O 0.28318(7) 0.2881(3) 0.14153(16) 0.0243(4) Uani 1 1 d . . . . .
C16 C 0.27989(10) 0.1048(5) 0.0538(2) 0.0283(6) Uani 1 1 d . . . . .
H16A H 0.240831 0.084723 0.015090 0.042 Uiso 1 1 calc R U . . .
H16B H 0.292589 -0.025314 0.104493 0.042 Uiso 1 1 calc R U . . .
H16C H 0.303989 0.129047 -0.018400 0.042 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
C1 C1 1.345(4) 2_656 ?
C1 C5 1.480(3) . ?
C1 C2 1.534(3) . ?
C2 C10 1.533(3) . ?
C2 C3 1.556(3) . ?
C2 H2 1.0000 . ?
C3 C4 1.514(3) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 C9 1.387(3) . ?
C4 C5 1.396(3) . ?
C5 C6 1.399(3) . ?
C6 O1 1.379(3) . ?
C6 C7 1.393(3) . ?
C7 O2 1.381(3) . ?
C7 C8 1.399(3) . ?
C8 O3 1.367(3) . ?
C8 C9 1.395(3) . ?
C9 H9 0.9500 . ?
C10 C11 1.540(3) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 C13 1.522(4) . ?
C11 C12 1.525(4) . ?
C11 H11 1.0000 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
O1 C14 1.429(3) . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
O2 C15 1.429(3) . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
O3 C16 1.428(3) . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 C1 C5 127.3(2) 2_656 . ?
C1 C1 C2 125.2(2) 2_656 . ?
C5 C1 C2 104.96(17) . . ?
C10 C2 C1 113.39(18) . . ?
C10 C2 C3 111.03(17) . . ?
C1 C2 C3 100.95(17) . . ?
C10 C2 H2 110.4 . . ?
C1 C2 H2 110.4 . . ?
C3 C2 H2 110.4 . . ?
C4 C3 C2 102.65(18) . . ?
C4 C3 H3A 111.2 . . ?
C2 C3 H3A 111.2 . . ?
C4 C3 H3B 111.2 . . ?
C2 C3 H3B 111.2 . . ?
H3A C3 H3B 109.2 . . ?
C9 C4 C5 122.1(2) . . ?
C9 C4 C3 128.0(2) . . ?
C5 C4 C3 109.87(19) . . ?
C4 C5 C6 119.03(19) . . ?
C4 C5 C1 108.62(19) . . ?
C6 C5 C1 132.3(2) . . ?
O1 C6 C7 118.82(19) . . ?
O1 C6 C5 121.68(19) . . ?
C7 C6 C5 119.5(2) . . ?
O2 C7 C6 119.5(2) . . ?
O2 C7 C8 120.03(19) . . ?
C6 C7 C8 120.4(2) . . ?
O3 C8 C9 124.1(2) . . ?
O3 C8 C7 115.4(2) . . ?
C9 C8 C7 120.5(2) . . ?
C4 C9 C8 118.2(2) . . ?
C4 C9 H9 120.9 . . ?
C8 C9 H9 120.9 . . ?
C2 C10 C11 114.99(19) . . ?
C2 C10 H10A 108.5 . . ?
C11 C10 H10A 108.5 . . ?
C2 C10 H10B 108.5 . . ?
C11 C10 H10B 108.5 . . ?
H10A C10 H10B 107.5 . . ?
C13 C11 C12 110.0(2) . . ?
C13 C11 C10 112.12(19) . . ?
C12 C11 C10 110.1(2) . . ?
C13 C11 H11 108.1 . . ?
C12 C11 H11 108.1 . . ?
C10 C11 H11 108.1 . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C11 C13 H13A 109.5 . . ?
C11 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C11 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C6 O1 C14 112.27(16) . . ?
O1 C14 H14A 109.5 . . ?
O1 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
O1 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C7 O2 C15 113.89(19) . . ?
O2 C15 H15A 109.5 . . ?
O2 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
O2 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C8 O3 C16 117.56(19) . . ?
O3 C16 H16A 109.5 . . ?
O3 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
O3 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?

_refine_diff_density_max         0.181
_refine_diff_density_min         -0.226
_refine_diff_density_rms         0.051

####################################################################### 
# 
# 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_mo_molan589_0m_a
_database_code_depnum_ccdc_archive 'CCDC 2127293'
loop_
_audit_author_name
_audit_author_address
'Folkert de Vries'
;University of Groningen
Netherlands
;
_audit_update_record             
;
2021-12-08 deposited with the CCDC.	2022-03-11 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/1
_shelx_SHELXL_version_number     2018/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_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 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_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'
'-x, -y, -z'

_cell_length_a                   11.0534(16)
_cell_length_b                   11.5940(17)
_cell_length_c                   12.4153(18)
_cell_angle_alpha                75.979(5)
_cell_angle_beta                 86.095(5)
_cell_angle_gamma                73.276(4)
_cell_volume                     1478.4(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    1535
_cell_measurement_theta_min      3.38
_cell_measurement_theta_max      22.95

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.241
_exptl_crystal_F_000             592
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.473
_exptl_crystal_size_mid          0.296
_exptl_crystal_size_min          0.142
_exptl_absorpt_coefficient_mu    0.088
_shelx_estimated_absorpt_T_min   0.959
_shelx_estimated_absorpt_T_max   0.988
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5076
_exptl_absorpt_correction_T_max  0.7453
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            19212
_diffrn_reflns_av_unetI/netI     0.1416
_diffrn_reflns_av_R_equivalents  0.1264
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.571
_diffrn_reflns_theta_max         26.083
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             5834
_reflns_number_gt                3476
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_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)+(0.0247P)²+0.0453P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5834
_refine_ls_number_parameters     371
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1187
_refine_ls_R_factor_gt           0.0666
_refine_ls_wR_factor_ref         0.1770
_refine_ls_wR_factor_gt          0.1478
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_restrained_S_all      1.029
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.27302(18) 0.4728(2) 0.29756(17) 0.0299(5) Uani 1 1 d . . . . .
C1 C 0.3015(2) 0.5169(3) 0.5735(2) 0.0235(7) Uani 1 1 d . . . . .
H1A H 0.334829 0.584027 0.584137 0.028 Uiso 1 1 calc R U . . .
H1B H 0.244654 0.497046 0.636050 0.028 Uiso 1 1 calc R U . . .
O2 O 0.48658(17) 0.23130(19) 0.34389(16) 0.0249(5) Uani 1 1 d . . . . .
C2 C 0.4072(2) 0.4038(3) 0.5638(2) 0.0203(6) Uani 1 1 d . . . . .
O3 O 0.67618(17) 0.09855(18) 0.49365(17) 0.0267(5) Uani 1 1 d . . . . .
C3 C 0.5004(2) 0.3358(3) 0.6432(2) 0.0213(6) Uani 1 1 d . . . . .
H3 H 0.502989 0.358562 0.711398 0.026 Uiso 1 1 calc R U . . .
C4 C 0.5892(2) 0.2335(3) 0.6186(2) 0.0216(6) Uani 1 1 d . . . . .
O4 O 0.68602(17) 0.15877(19) 0.68890(17) 0.0264(5) Uani 1 1 d . . . . .
O5 O 0.60824(18) 0.5840(2) 0.11779(18) 0.0320(5) Uani 1 1 d . . . . .
C5 C 0.5849(2) 0.1977(3) 0.5179(2) 0.0231(7) Uani 1 1 d . . . . .
O6 O 0.74196(17) 0.32566(19) 0.06980(17) 0.0272(5) Uani 1 1 d . . . . .
C6 C 0.4922(2) 0.2679(3) 0.4401(2) 0.0211(6) Uani 1 1 d . . . . .
O7 O 0.97557(18) 0.16795(19) 0.06209(18) 0.0293(5) Uani 1 1 d . . . . .
C7 C 0.4037(2) 0.3732(3) 0.4628(2) 0.0207(6) Uani 1 1 d . . . . .
C8 C 0.3000(3) 0.4660(3) 0.3934(3) 0.0245(7) Uani 1 1 d . . . . .
O8 O 1.17861(17) 0.2100(2) 0.12894(18) 0.0316(5) Uani 1 1 d . . . . .
C9 C 0.2339(2) 0.5528(3) 0.4634(2) 0.0230(7) Uani 1 1 d . . . . .
C10 C 0.1284(3) 0.6432(3) 0.4301(3) 0.0274(7) Uani 1 1 d . . . . .
H10 H 0.100244 0.655020 0.356538 0.033 Uiso 1 1 calc R U . . .
C11 C 0.0509(3) 0.7270(3) 0.4983(3) 0.0311(7) Uani 1 1 d . . . . .
H11 H 0.102841 0.724217 0.562306 0.037 Uiso 1 1 calc R U . . .
C12 C -0.0649(3) 0.6821(3) 0.5432(3) 0.0391(9) Uani 1 1 d . . . . .
H12A H -0.115797 0.683792 0.480836 0.059 Uiso 1 1 calc R U . . .
H12B H -0.115988 0.736577 0.588624 0.059 Uiso 1 1 calc R U . . .
H12C H -0.036825 0.597289 0.588537 0.059 Uiso 1 1 calc R U . . .
C13 C 0.0080(3) 0.8614(3) 0.4285(3) 0.0380(9) Uani 1 1 d . . . . .
H13A H 0.082272 0.890466 0.403017 0.057 Uiso 1 1 calc R U . . .
H13B H -0.045087 0.914658 0.474020 0.057 Uiso 1 1 calc R U . . .
H13C H -0.040460 0.864316 0.364204 0.057 Uiso 1 1 calc R U . . .
C14 C 0.7015(3) 0.1986(3) 0.7862(2) 0.0304(7) Uani 1 1 d . . . . .
H14A H 0.712819 0.281956 0.764529 0.046 Uiso 1 1 calc R U . . .
H14B H 0.775932 0.141255 0.827567 0.046 Uiso 1 1 calc R U . . .
H14C H 0.626357 0.199985 0.833089 0.046 Uiso 1 1 calc R U . . .
C15 C 0.6707(3) -0.0197(3) 0.5602(3) 0.0362(8) Uani 1 1 d . . . . .
H15A H 0.582281 -0.018917 0.574876 0.054 Uiso 1 1 calc R U . . .
H15B H 0.714704 -0.036614 0.630684 0.054 Uiso 1 1 calc R U . . .
H15C H 0.711430 -0.084245 0.520523 0.054 Uiso 1 1 calc R U . . .
C16 C 0.5600(3) 0.2837(3) 0.2553(3) 0.0313(8) Uani 1 1 d . . . . .
H16A H 0.554978 0.252249 0.189721 0.047 Uiso 1 1 calc R U . . .
H16B H 0.648298 0.260339 0.278928 0.047 Uiso 1 1 calc R U . . .
H16C H 0.526664 0.374131 0.236970 0.047 Uiso 1 1 calc R U . . .
C17 C 0.9080(3) 0.6252(3) 0.1744(3) 0.0289(7) Uani 1 1 d . . . . .
H17A H 0.928844 0.619198 0.252259 0.035 Uiso 1 1 calc R U . . .
H17B H 0.953802 0.678826 0.124232 0.035 Uiso 1 1 calc R U . . .
C18 C 0.9409(3) 0.4988(3) 0.1496(2) 0.0250(7) Uani 1 1 d . . . . .
C19 C 1.0596(3) 0.4136(3) 0.1541(2) 0.0254(7) Uani 1 1 d . . . . .
H19 H 1.132073 0.431830 0.174472 0.031 Uiso 1 1 calc R U . . .
C20 C 1.0696(3) 0.3021(3) 0.1282(2) 0.0240(7) Uani 1 1 d . . . . .
C21 C 0.9617(3) 0.2756(3) 0.0966(2) 0.0238(7) Uani 1 1 d . . . . .
C22 C 0.8437(2) 0.3603(3) 0.0940(2) 0.0217(6) Uani 1 1 d . . . . .
C23 C 0.8325(3) 0.4724(3) 0.1216(2) 0.0236(7) Uani 1 1 d . . . . .
C24 C 0.7197(3) 0.5776(3) 0.1289(2) 0.0263(7) Uani 1 1 d . . . . .
C25 C 0.7677(3) 0.6747(3) 0.1545(2) 0.0258(7) Uani 1 1 d . . . . .
C26 C 0.6918(3) 0.7875(3) 0.1522(2) 0.0289(7) Uani 1 1 d . . . . .
H26 H 0.605472 0.800295 0.136272 0.035 Uiso 1 1 calc R U . . .
C27 C 0.7258(3) 0.8960(3) 0.1717(3) 0.0315(7) Uani 1 1 d . . . . .
H27 H 0.818412 0.871121 0.187746 0.038 Uiso 1 1 calc R U . . .
C28 C 0.6535(3) 0.9368(3) 0.2719(3) 0.0391(9) Uani 1 1 d . . . . .
H28A H 0.680600 1.004706 0.287038 0.059 Uiso 1 1 calc R U . . .
H28B H 0.670801 0.866838 0.336912 0.059 Uiso 1 1 calc R U . . .
H28C H 0.562667 0.964979 0.255917 0.059 Uiso 1 1 calc R U . . .
C29 C 0.6976(3) 1.0015(3) 0.0670(3) 0.0433(9) Uani 1 1 d . . . . .
H29A H 0.747525 0.973864 0.004902 0.065 Uiso 1 1 calc R U . . .
H29B H 0.719821 1.072973 0.079997 0.065 Uiso 1 1 calc R U . . .
H29C H 0.607520 1.025132 0.049019 0.065 Uiso 1 1 calc R U . . .
C30 C 1.2933(3) 0.2330(3) 0.1550(3) 0.0351(8) Uani 1 1 d . . . . .
H30A H 1.364603 0.159691 0.154259 0.053 Uiso 1 1 calc R U . . .
H30B H 1.286001 0.250765 0.228758 0.053 Uiso 1 1 calc R U . . .
H30C H 1.307322 0.304052 0.099593 0.053 Uiso 1 1 calc R U . . .
C31 C 0.9799(3) 0.0634(3) 0.1528(3) 0.0387(9) Uani 1 1 d . . . . .
H31A H 0.901213 0.079169 0.195354 0.058 Uiso 1 1 calc R U . . .
H31B H 1.051519 0.050021 0.201182 0.058 Uiso 1 1 calc R U . . .
H31C H 0.989770 -0.010347 0.124065 0.058 Uiso 1 1 calc R U . . .
C32 C 0.6794(3) 0.3963(3) -0.0331(3) 0.0357(8) Uani 1 1 d . . . . .
H32A H 0.740424 0.391486 -0.094072 0.054 Uiso 1 1 calc R U . . .
H32B H 0.643790 0.482914 -0.029080 0.054 Uiso 1 1 calc R U . . .
H32C H 0.611460 0.362555 -0.046191 0.054 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C8 1.225(4) . ?
C1 C2 1.509(4) . ?
C1 C9 1.512(4) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
O2 C6 1.372(3) . ?
O2 C16 1.441(3) . ?
C2 C7 1.389(4) . ?
C2 C3 1.396(4) . ?
O3 C5 1.374(3) . ?
O3 C15 1.434(4) . ?
C3 C4 1.388(4) . ?
C3 H3 0.9500 . ?
C4 O4 1.373(3) . ?
C4 C5 1.417(4) . ?
O4 C14 1.430(4) . ?
O5 C24 1.228(3) . ?
C5 C6 1.385(4) . ?
O6 C22 1.371(3) . ?
O6 C32 1.438(4) . ?
C6 C7 1.403(4) . ?
O7 C21 1.381(4) . ?
O7 C31 1.433(4) . ?
C7 C8 1.480(4) . ?
C8 C9 1.488(4) . ?
O8 C20 1.359(3) . ?
O8 C30 1.440(3) . ?
C9 C10 1.336(4) . ?
C10 C11 1.489(4) . ?
C10 H10 0.9500 . ?
C11 C12 1.539(4) . ?
C11 C13 1.542(4) . ?
C11 H11 1.0000 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C17 C25 1.506(4) . ?
C17 C18 1.508(4) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C18 C19 1.392(4) . ?
C18 C23 1.402(4) . ?
C19 C20 1.378(4) . ?
C19 H19 0.9500 . ?
C20 C21 1.415(4) . ?
C21 C22 1.386(4) . ?
C22 C23 1.394(4) . ?
C23 C24 1.488(4) . ?
C24 C25 1.480(4) . ?
C25 C26 1.329(4) . ?
C26 C27 1.488(4) . ?
C26 H26 0.9500 . ?
C27 C28 1.531(4) . ?
C27 C29 1.533(4) . ?
C27 H27 1.0000 . ?
C28 H28A 0.9800 . ?
C28 H28B 0.9800 . ?
C28 H28C 0.9800 . ?
C29 H29A 0.9800 . ?
C29 H29B 0.9800 . ?
C29 H29C 0.9800 . ?
C30 H30A 0.9800 . ?
C30 H30B 0.9800 . ?
C30 H30C 0.9800 . ?
C31 H31A 0.9800 . ?
C31 H31B 0.9800 . ?
C31 H31C 0.9800 . ?
C32 H32A 0.9800 . ?
C32 H32B 0.9800 . ?
C32 H32C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 C9 102.9(2) . . ?
C2 C1 H1A 111.2 . . ?
C9 C1 H1A 111.2 . . ?
C2 C1 H1B 111.2 . . ?
C9 C1 H1B 111.2 . . ?
H1A C1 H1B 109.1 . . ?
C6 O2 C16 113.0(2) . . ?
C7 C2 C3 122.0(3) . . ?
C7 C2 C1 111.8(2) . . ?
C3 C2 C1 126.2(3) . . ?
C5 O3 C15 114.4(2) . . ?
C4 C3 C2 117.3(3) . . ?
C4 C3 H3 121.3 . . ?
C2 C3 H3 121.3 . . ?
O4 C4 C3 123.4(3) . . ?
O4 C4 C5 114.8(3) . . ?
C3 C4 C5 121.7(3) . . ?
C4 O4 C14 116.6(2) . . ?
O3 C5 C6 119.5(3) . . ?
O3 C5 C4 120.7(3) . . ?
C6 C5 C4 119.6(3) . . ?
C22 O6 C32 114.7(2) . . ?
O2 C6 C5 119.4(3) . . ?
O2 C6 C7 121.3(2) . . ?
C5 C6 C7 119.2(3) . . ?
C21 O7 C31 112.7(3) . . ?
C2 C7 C6 120.0(3) . . ?
C2 C7 C8 109.7(3) . . ?
C6 C7 C8 130.2(3) . . ?
O1 C8 C7 128.0(3) . . ?
O1 C8 C9 126.0(3) . . ?
C7 C8 C9 105.9(3) . . ?
C20 O8 C30 117.2(2) . . ?
C10 C9 C8 122.3(3) . . ?
C10 C9 C1 128.2(3) . . ?
C8 C9 C1 109.5(2) . . ?
C9 C10 C11 125.6(3) . . ?
C9 C10 H10 117.2 . . ?
C11 C10 H10 117.2 . . ?
C10 C11 C12 109.1(3) . . ?
C10 C11 C13 110.6(3) . . ?
C12 C11 C13 110.0(2) . . ?
C10 C11 H11 109.0 . . ?
C12 C11 H11 109.0 . . ?
C13 C11 H11 109.0 . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C11 C13 H13A 109.5 . . ?
C11 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C11 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
O4 C14 H14A 109.5 . . ?
O4 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
O4 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
O3 C15 H15A 109.5 . . ?
O3 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
O3 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
O2 C16 H16A 109.5 . . ?
O2 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
O2 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C25 C17 C18 103.8(2) . . ?
C25 C17 H17A 111.0 . . ?
C18 C17 H17A 111.0 . . ?
C25 C17 H17B 111.0 . . ?
C18 C17 H17B 111.0 . . ?
H17A C17 H17B 109.0 . . ?
C19 C18 C23 121.5(3) . . ?
C19 C18 C17 127.5(3) . . ?
C23 C18 C17 111.0(3) . . ?
C20 C19 C18 118.5(3) . . ?
C20 C19 H19 120.7 . . ?
C18 C19 H19 120.7 . . ?
O8 C20 C19 125.3(3) . . ?
O8 C20 C21 114.1(3) . . ?
C19 C20 C21 120.6(3) . . ?
O7 C21 C22 119.9(3) . . ?
O7 C21 C20 119.6(3) . . ?
C22 C21 C20 120.4(3) . . ?
O6 C22 C21 117.5(3) . . ?
O6 C22 C23 123.2(3) . . ?
C21 C22 C23 119.3(3) . . ?
C22 C23 C18 119.6(3) . . ?
C22 C23 C24 131.0(3) . . ?
C18 C23 C24 109.4(3) . . ?
O5 C24 C25 125.9(3) . . ?
O5 C24 C23 127.8(3) . . ?
C25 C24 C23 106.2(2) . . ?
C26 C25 C24 121.2(3) . . ?
C26 C25 C17 129.4(3) . . ?
C24 C25 C17 109.3(3) . . ?
C25 C26 C27 127.8(3) . . ?
C25 C26 H26 116.1 . . ?
C27 C26 H26 116.1 . . ?
C26 C27 C28 110.1(3) . . ?
C26 C27 C29 109.6(3) . . ?
C28 C27 C29 111.2(3) . . ?
C26 C27 H27 108.6 . . ?
C28 C27 H27 108.6 . . ?
C29 C27 H27 108.6 . . ?
C27 C28 H28A 109.5 . . ?
C27 C28 H28B 109.5 . . ?
H28A C28 H28B 109.5 . . ?
C27 C28 H28C 109.5 . . ?
H28A C28 H28C 109.5 . . ?
H28B C28 H28C 109.5 . . ?
C27 C29 H29A 109.5 . . ?
C27 C29 H29B 109.5 . . ?
H29A C29 H29B 109.5 . . ?
C27 C29 H29C 109.5 . . ?
H29A C29 H29C 109.5 . . ?
H29B C29 H29C 109.5 . . ?
O8 C30 H30A 109.5 . . ?
O8 C30 H30B 109.5 . . ?
H30A C30 H30B 109.5 . . ?
O8 C30 H30C 109.5 . . ?
H30A C30 H30C 109.5 . . ?
H30B C30 H30C 109.5 . . ?
O7 C31 H31A 109.5 . . ?
O7 C31 H31B 109.5 . . ?
H31A C31 H31B 109.5 . . ?
O7 C31 H31C 109.5 . . ?
H31A C31 H31C 109.5 . . ?
H31B C31 H31C 109.5 . . ?
O6 C32 H32A 109.5 . . ?
O6 C32 H32B 109.5 . . ?
H32A C32 H32B 109.5 . . ?
O6 C32 H32C 109.5 . . ?
H32A C32 H32C 109.5 . . ?
H32B C32 H32C 109.5 . . ?

_refine_diff_density_max         0.377
_refine_diff_density_min         -0.306
_refine_diff_density_rms         0.062

