# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2021

####################################################################### 
# 
# 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. 
# 
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data_RB_USP_HS_MD01_02_Cu
_database_code_depnum_ccdc_archive 'CCDC 2085190'
loop_
_audit_author_name
_audit_author_address
'Robert Burrow'
;Universidade Federal de Santa MAria
Brazil
;
_audit_update_record             
;
2021-05-21 deposited with the CCDC.	2021-12-10 downloaded from the CCDC.
;
_chemical_name_systematic        
1-(4,5-dihydroxy-6-(hydroxymethyl)-5,6-dihydro-4H-pyran-3-yl)-3-p-tolylprop-2-yn-1-one
_chemical_formula_moiety         'C16 H16 O5'
_chemical_formula_sum            'C16 H16 O5'
_chemical_formula_iupac          ?
_chemical_formula_weight         288.29
_chemical_absolute_configuration ad

_chemical_melting_point          ?

_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   6.27541(14)
_cell_length_b                   9.9710(2)
_cell_length_c                   23.3558(6)
_cell_angle_alpha                90
_cell_angle_beta                 91.2091(12)
_cell_angle_gamma                90
_cell_volume                     1461.10(6)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9933
_cell_measurement_theta_min      3.7860
_cell_measurement_theta_max      71.7499
_cell_measurement_temperature    296.(2)

_exptl_crystal_description       'flat needle'
_exptl_crystal_colour            'pale yellow'
_exptl_crystal_size_max          0.414
_exptl_crystal_size_mid          0.052
_exptl_crystal_size_min          0.021
_exptl_crystal_density_diffrn    1.311
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             608

_exptl_absorpt_coefficient_mu    0.813
_exptl_absorpt_correction_type   Multi-Scan
_exptl_absorpt_process_details   
;
SADABS (version 2016/2; Bruker, 2016) was used to perform the multi--scan
absorption correction.
;
_exptl_absorpt_correction_T_min  0.89
_exptl_absorpt_correction_T_max  1.00

_exptl_special_details           
;
;

_diffrn_ambient_temperature      296.(2)

_diffrn_source                   'microfocus X ray tube'
_diffrn_source_type              'Incoatex I\mS High Brilliance'

_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_monochromator  'Incoatec Montel two dimensional X ray optics'

_diffrn_measurement_device_type  'Bruker D8 Quest Photon 100 diffractometer'
_diffrn_measurement_method       '0.5 ° ω & φ scans'

_diffrn_detector_area_resol_mean 10.4167

_diffrn_reflns_number            62151
_diffrn_reflns_av_R_equivalents  0.0907
_diffrn_reflns_av_unetI/netI     0.0300
_diffrn_reflns_theta_min         3.79
_diffrn_reflns_theta_max         72.26
_diffrn_reflns_theta_full        72.26
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_limit_l_max       28

_refine_special_details          
;

Refined as a 2-component inversion twin.
;

_reflns_number_total             5778
_reflns_number_gt                4520
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0648
_refine_ls_R_factor_gt           0.0475
_refine_ls_wR_factor_gt          0.1250
_refine_ls_wR_factor_ref         0.1396
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_restrained_S_all      1.031
_refine_ls_number_reflns         5778
_refine_ls_number_parameters     406
_refine_ls_number_restraints     7
_refine_ls_number_constraints    ?
_refine_ls_hydrogen_treatment    mixed
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0798P)²+0.1555P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap

_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.235
_refine_diff_density_min         -0.155
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_extinction_coef       0.0032(8)
_refine_ls_abs_structure_details 
;

Flack x determined using 1743 quotients [(I+)-(I-)]/[(I+)+(I-)]
(Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.04(11)

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'

_computing_data_collection       'APEX3 v2019.1-2 (Bruker AXS Inc., 2019)'
_computing_cell_refinement       'SAINT V8.40A (Bruker Nano, Inc., 2019)'
_computing_data_reduction        'SAINT V8.40A (Bruker Nano, Inc., 2019)'
_computing_structure_solution    'XT, VERSION 2014/5'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'shelXle (C.B. Huebschle, rev 958)'
_computing_publication_material  Vim

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O O1 0.5452(5) 0.4555(3) 0.42697(14) 0.0617(7) Uani d . . D 1 . .
H H1O 0.445(7) 0.422(6) 0.444(2) 0.085(18) Uiso d . . D 1 . .
O O2 0.4049(4) 0.6453(3) 0.51570(13) 0.0555(7) Uani d . . . 1 . .
O O3 0.7476(5) 0.8329(3) 0.51242(16) 0.0689(8) Uani d . . D 1 . .
H H3O 0.864(6) 0.870(5) 0.512(2) 0.079(16) Uiso d . . D 1 . .
O O4 0.9259(5) 0.4989(3) 0.47218(13) 0.0603(7) Uani d . . D 1 . .
H H4O 0.809(7) 0.472(7) 0.457(2) 0.10(2) Uiso d . . D 1 . .
O O5 1.0209(5) 0.4585(4) 0.60404(15) 0.0859(11) Uani d . . . 1 . .
C C1 0.4629(7) 0.5869(5) 0.41714(19) 0.0631(11) Uani d . . . 1 . .
H H1A 0.309254 0.581205 0.412326 0.076 Uiso calc U . R 1 . .
H H1B 0.519611 0.620955 0.381674 0.076 Uiso calc U . R 1 . .
C C2 0.5151(6) 0.6859(4) 0.46485(19) 0.0548(9) Uani d . . . 1 . .
H H2 0.45037 0.771202 0.452939 0.066 Uiso calc U . R 1 . .
C C3 0.7478(6) 0.7163(4) 0.4776(2) 0.0543(9) Uani d . . . 1 . .
H H3 0.820581 0.735438 0.44176 0.065 Uiso calc U . R 1 . .
C C4 0.8636(5) 0.6039(4) 0.50967(17) 0.0507(8) Uani d . . . 1 . .
H H4 0.993117 0.64179 0.527422 0.061 Uiso calc U . R 1 . .
C C5 0.7247(6) 0.5542(4) 0.55666(17) 0.0489(8) Uani d . . . 1 . .
C C6 0.5149(5) 0.5769(4) 0.55621(17) 0.0488(8) Uani d . . . 1 . .
H H6 0.438294 0.542518 0.586528 0.059 Uiso calc U . R 1 . .
C C7 0.8280(6) 0.4752(5) 0.60279(18) 0.0600(10) Uani d . . . 1 . .
C C8 0.6940(8) 0.4158(5) 0.6454(2) 0.0676(11) Uani d . . . 1 . .
C C9 0.5807(8) 0.3619(5) 0.6788(2) 0.0681(11) Uani d . . . 1 . .
C C10 0.4423(8) 0.2981(5) 0.71881(18) 0.0650(11) Uani d . . . 1 . .
C C11 0.5094(10) 0.1878(6) 0.7510(2) 0.0861(16) Uani d . . . 1 . .
H H11 0.644802 0.152457 0.745768 0.103 Uiso calc U . R 1 . .
C C12 0.3783(10) 0.1309(7) 0.7901(3) 0.0919(18) Uani d . . . 1 . .
H H12 0.426958 0.057687 0.811255 0.11 Uiso calc U . R 1 . .
C C13 0.1761(9) 0.1790(6) 0.7990(2) 0.0794(14) Uani d . . . 1 . .
C C14 0.1097(9) 0.2893(6) 0.7668(2) 0.0788(13) Uani d . . . 1 . .
H H14 -0.024815 0.325247 0.772686 0.095 Uiso calc U . R 1 . .
C C15 0.2376(8) 0.3463(6) 0.7266(2) 0.0745(13) Uani d . . . 1 . .
H H15 0.186902 0.417485 0.70453 0.089 Uiso calc U . R 1 . .
C C16 0.0332(12) 0.1166(9) 0.8429(3) 0.111(2) Uani d . . . 1 . .
H H16A -0.112016 0.119778 0.829228 0.167 Uiso calc U . R 1 . .
H H16B 0.04642 0.165458 0.878227 0.167 Uiso calc U . R 1 . .
H H16C 0.074506 0.024993 0.84919 0.167 Uiso calc U . R 1 . .
O O1' 0.5384(5) 0.4726(3) 1.07330(14) 0.0632(7) Uani d . . D 1 . .
H H1O' 0.449(9) 0.515(6) 1.052(2) 0.10(2) Uiso d . . D 1 . .
O O2' 0.3941(4) 0.2821(3) 0.98112(13) 0.0564(7) Uani d . . . 1 . .
O O3' 0.7523(4) 0.1009(3) 0.98840(16) 0.0680(8) Uani d . . D 1 . .
H H3O' 0.866(5) 0.060(5) 0.990(2) 0.073(15) Uiso d . . D 1 . .
O O4' 0.9142(4) 0.4403(3) 1.02662(13) 0.0588(7) Uani d . . D 1 . .
H H4O' 0.796(5) 0.465(5) 1.0402(19) 0.068(14) Uiso d . . D 1 . .
O O5' 0.9943(5) 0.4756(4) 0.89485(15) 0.0817(10) Uani d . . . 1 . .
C C1' 0.4581(7) 0.3413(5) 1.0805(2) 0.0644(11) Uani d . . . 1 . .
H H1C 0.304365 0.34639 1.083402 0.077 Uiso calc U . R 1 . .
H H1D 0.514149 0.305737 1.116398 0.077 Uiso calc U . R 1 . .
C C2' 0.5109(6) 0.2440(4) 1.03299(18) 0.0545(9) Uani d . . . 1 . .
H H2' 0.452486 0.157233 1.044541 0.065 Uiso calc U . R 1 . .
C C3' 0.7456(6) 0.2196(4) 1.02173(18) 0.0527(9) Uani d . . . 1 . .
H H3' 0.82199 0.204751 1.058207 0.063 Uiso calc U . R 1 . .
C C4' 0.8516(5) 0.3329(4) 0.98946(17) 0.0491(8) Uani d . . . 1 . .
H H4' 0.980917 0.296742 0.972403 0.059 Uiso calc U . R 1 . .
C C5' 0.7063(5) 0.3786(4) 0.94151(16) 0.0479(8) Uani d . . . 1 . .
C C6' 0.4982(6) 0.3514(4) 0.94104(17) 0.0504(8) Uani d . . . 1 . .
H H6' 0.417501 0.383466 0.910103 0.06 Uiso calc U . R 1 . .
C C7' 0.8021(6) 0.4558(4) 0.89554(17) 0.0572(9) Uani d . . . 1 . .
C C8' 0.6616(8) 0.5129(5) 0.85163(19) 0.0672(11) Uani d . . . 1 . .
C C9' 0.5478(9) 0.5712(5) 0.81810(19) 0.0700(12) Uani d . . . 1 . .
C C10' 0.4092(8) 0.6472(5) 0.78096(19) 0.0648(11) Uani d . . . 1 . .
C C11' 0.4800(9) 0.6999(6) 0.7296(2) 0.0766(13) Uani d . . . 1 . .
H H11' 0.618356 0.682717 0.718117 0.092 Uiso calc U . R 1 . .
C C12' 0.3478(10) 0.7766(7) 0.6959(2) 0.0877(16) Uani d . . . 1 . .
H H12' 0.397051 0.809162 0.661318 0.105 Uiso calc U . R 1 . .
C C13' 0.1430(9) 0.8072(7) 0.7119(2) 0.0910(18) Uani d . . . 1 . .
C C14' 0.0733(9) 0.7550(8) 0.7631(2) 0.0907(17) Uani d . . . 1 . .
H H14' -0.063442 0.774875 0.775201 0.109 Uiso calc U . R 1 . .
C C15' 0.2039(9) 0.6735(6) 0.7967(2) 0.0784(14) Uani d . . . 1 . .
H H15' 0.15209 0.636341 0.8302 0.094 Uiso calc U . R 1 . .
C C16' -0.0038(13) 0.8979(10) 0.6759(3) 0.140(3) Uani d . . . 1 . .
H H16D -0.029984 0.857386 0.639095 0.21 Uiso calc U . R 1 . .
H H16E 0.063015 0.983602 0.67089 0.21 Uiso calc U . R 1 . .
H H16F -0.136424 0.909575 0.694983 0.21 Uiso calc U . R 1 . .


_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_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
O1 C1 . 1.425(5) ?
O1 H1O . 0.83(3) ?
O2 C6 . 1.345(5) ?
O2 C2 . 1.445(5) ?
O3 C3 . 1.419(5) ?
O3 H3O . 0.82(3) ?
O4 C4 . 1.425(5) ?
O4 H4O . 0.85(3) ?
O5 C7 . 1.222(5) ?
C1 C2 . 1.520(6) ?
C1 H1A . 0.97 ?
C1 H1B . 0.97 ?
C2 C3 . 1.515(6) ?
C2 H2 . 0.98 ?
C3 C4 . 1.525(5) ?
C3 H3 . 0.98 ?
C4 C5 . 1.500(5) ?
C4 H4 . 0.98 ?
C5 C6 . 1.336(5) ?
C5 C7 . 1.473(5) ?
C6 H6 . 0.93 ?
C7 C8 . 1.443(7) ?
C8 C9 . 1.195(7) ?
C9 C10 . 1.437(7) ?
C10 C15 . 1.387(7) ?
C10 C11 . 1.392(7) ?
C11 C12 . 1.365(8) ?
C11 H11 . 0.93 ?
C12 C13 . 1.376(9) ?
C12 H12 . 0.93 ?
C13 C14 . 1.391(7) ?
C13 C16 . 1.511(8) ?
C14 C15 . 1.371(7) ?
C14 H14 . 0.93 ?
C15 H15 . 0.93 ?
C16 H16A . 0.96 ?
C16 H16B . 0.96 ?
C16 H16C . 0.96 ?
O1' C1' . 1.414(6) ?
O1' H1O' . 0.86(3) ?
O2' C6' . 1.344(5) ?
O2' C2' . 1.453(5) ?
O3' C3' . 1.417(5) ?
O3' H3O' . 0.82(3) ?
O4' C4' . 1.428(5) ?
O4' H4O' . 0.85(3) ?
O5' C7' . 1.222(5) ?
C1' C2' . 1.515(6) ?
C1' H1C . 0.97 ?
C1' H1D . 0.97 ?
C2' C3' . 1.521(5) ?
C2' H2' . 0.98 ?
C3' C4' . 1.519(5) ?
C3' H3' . 0.98 ?
C4' C5' . 1.500(5) ?
C4' H4' . 0.98 ?
C5' C6' . 1.334(5) ?
C5' C7' . 1.461(6) ?
C6' H6' . 0.93 ?
C7' C8' . 1.454(6) ?
C8' C9' . 1.199(6) ?
C9' C10' . 1.432(7) ?
C10' C15' . 1.373(8) ?
C10' C11' . 1.391(7) ?
C11' C12' . 1.366(8) ?
C11' H11' . 0.93 ?
C12' C13' . 1.380(9) ?
C12' H12' . 0.93 ?
C13' C14' . 1.384(8) ?
C13' C16' . 1.530(9) ?
C14' C15' . 1.386(8) ?
C14' H14' . 0.93 ?
C15' H15' . 0.93 ?
C16' H16D . 0.96 ?
C16' H16E . 0.96 ?
C16' H16F . 0.96 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C1 O1 H1O . . 100.(4) ?
C6 O2 C2 . . 118.2(3) ?
C3 O3 H3O . . 110.(4) ?
C4 O4 H4O . . 104.(5) ?
O1 C1 C2 . . 114.1(3) ?
O1 C1 H1A . . 108.7 ?
C2 C1 H1A . . 108.7 ?
O1 C1 H1B . . 108.7 ?
C2 C1 H1B . . 108.7 ?
H1A C1 H1B . . 107.6 ?
O2 C2 C3 . . 111.8(3) ?
O2 C2 C1 . . 108.7(3) ?
C3 C2 C1 . . 117.8(4) ?
O2 C2 H2 . . 105.9 ?
C3 C2 H2 . . 105.9 ?
C1 C2 H2 . . 105.9 ?
O3 C3 C2 . . 105.3(3) ?
O3 C3 C4 . . 109.0(3) ?
C2 C3 C4 . . 113.4(3) ?
O3 C3 H3 . . 109.7 ?
C2 C3 H3 . . 109.7 ?
C4 C3 H3 . . 109.7 ?
O4 C4 C5 . . 112.2(3) ?
O4 C4 C3 . . 111.9(3) ?
C5 C4 C3 . . 108.9(3) ?
O4 C4 H4 . . 107.9 ?
C5 C4 H4 . . 107.9 ?
C3 C4 H4 . . 107.9 ?
C6 C5 C7 . . 121.0(4) ?
C6 C5 C4 . . 121.7(3) ?
C7 C5 C4 . . 117.3(3) ?
C5 C6 O2 . . 125.7(4) ?
C5 C6 H6 . . 117.2 ?
O2 C6 H6 . . 117.2 ?
O5 C7 C8 . . 121.2(4) ?
O5 C7 C5 . . 120.7(4) ?
C8 C7 C5 . . 118.0(4) ?
C9 C8 C7 . . 176.9(5) ?
C8 C9 C10 . . 179.3(6) ?
C15 C10 C11 . . 118.2(5) ?
C15 C10 C9 . . 120.4(4) ?
C11 C10 C9 . . 121.3(5) ?
C12 C11 C10 . . 120.6(6) ?
C12 C11 H11 . . 119.7 ?
C10 C11 H11 . . 119.7 ?
C11 C12 C13 . . 121.8(5) ?
C11 C12 H12 . . 119.1 ?
C13 C12 H12 . . 119.1 ?
C12 C13 C14 . . 117.4(5) ?
C12 C13 C16 . . 121.4(5) ?
C14 C13 C16 . . 121.1(6) ?
C15 C14 C13 . . 121.6(5) ?
C15 C14 H14 . . 119.2 ?
C13 C14 H14 . . 119.2 ?
C14 C15 C10 . . 120.3(5) ?
C14 C15 H15 . . 119.9 ?
C10 C15 H15 . . 119.9 ?
C13 C16 H16A . . 109.5 ?
C13 C16 H16B . . 109.5 ?
H16A C16 H16B . . 109.5 ?
C13 C16 H16C . . 109.5 ?
H16A C16 H16C . . 109.5 ?
H16B C16 H16C . . 109.5 ?
C1' O1' H1O' . . 107.(5) ?
C6' O2' C2' . . 118.1(3) ?
C3' O3' H3O' . . 116.(4) ?
C4' O4' H4O' . . 102.(4) ?
O1' C1' C2' . . 115.0(4) ?
O1' C1' H1C . . 108.5 ?
C2' C1' H1C . . 108.5 ?
O1' C1' H1D . . 108.5 ?
C2' C1' H1D . . 108.5 ?
H1C C1' H1D . . 107.5 ?
O2' C2' C1' . . 109.2(3) ?
O2' C2' C3' . . 111.8(3) ?
C1' C2' C3' . . 117.2(4) ?
O2' C2' H2' . . 106.0 ?
C1' C2' H2' . . 106.0 ?
C3' C2' H2' . . 106.0 ?
O3' C3' C4' . . 109.2(3) ?
O3' C3' C2' . . 105.6(3) ?
C4' C3' C2' . . 113.7(3) ?
O3' C3' H3' . . 109.4 ?
C4' C3' H3' . . 109.4 ?
C2' C3' H3' . . 109.4 ?
O4' C4' C5' . . 112.4(3) ?
O4' C4' C3' . . 112.0(3) ?
C5' C4' C3' . . 109.3(3) ?
O4' C4' H4' . . 107.7 ?
C5' C4' H4' . . 107.7 ?
C3' C4' H4' . . 107.7 ?
C6' C5' C7' . . 121.3(3) ?
C6' C5' C4' . . 121.6(3) ?
C7' C5' C4' . . 117.1(3) ?
C5' C6' O2' . . 126.1(3) ?
C5' C6' H6' . . 117.0 ?
O2' C6' H6' . . 117.0 ?
O5' C7' C8' . . 120.8(4) ?
O5' C7' C5' . . 121.1(4) ?
C8' C7' C5' . . 118.1(4) ?
C9' C8' C7' . . 173.8(5) ?
C8' C9' C10' . . 176.2(5) ?
C15' C10' C11' . . 118.5(5) ?
C15' C10' C9' . . 120.0(4) ?
C11' C10' C9' . . 121.4(5) ?
C12' C11' C10' . . 120.5(6) ?
C12' C11' H11' . . 119.8 ?
C10' C11' H11' . . 119.8 ?
C11' C12' C13' . . 121.7(5) ?
C11' C12' H12' . . 119.1 ?
C13' C12' H12' . . 119.1 ?
C12' C13' C14' . . 117.6(5) ?
C12' C13' C16' . . 122.3(6) ?
C14' C13' C16' . . 120.0(6) ?
C13' C14' C15' . . 121.1(6) ?
C13' C14' H14' . . 119.5 ?
C15' C14' H14' . . 119.5 ?
C10' C15' C14' . . 120.5(5) ?
C10' C15' H15' . . 119.7 ?
C14' C15' H15' . . 119.7 ?
C13' C16' H16D . . 109.5 ?
C13' C16' H16E . . 109.5 ?
H16D C16' H16E . . 109.5 ?
C13' C16' H16F . . 109.5 ?
H16D C16' H16F . . 109.5 ?
H16E C16' H16F . . 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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C6 O2 C2 C3 . . . . -32.5(5) ?
C6 O2 C2 C1 . . . . 99.2(4) ?
O1 C1 C2 O2 . . . . -66.6(4) ?
O1 C1 C2 C3 . . . . 61.8(5) ?
O2 C2 C3 O3 . . . . -67.3(4) ?
C1 C2 C3 O3 . . . . 165.8(3) ?
O2 C2 C3 C4 . . . . 51.9(5) ?
C1 C2 C3 C4 . . . . -75.1(5) ?
O3 C3 C4 O4 . . . . -162.5(3) ?
C2 C3 C4 O4 . . . . 80.6(4) ?
O3 C3 C4 C5 . . . . 73.0(4) ?
C2 C3 C4 C5 . . . . -44.0(5) ?
O4 C4 C5 C6 . . . . -105.1(4) ?
C3 C4 C5 C6 . . . . 19.3(5) ?
O4 C4 C5 C7 . . . . 73.2(4) ?
C3 C4 C5 C7 . . . . -162.4(3) ?
C7 C5 C6 O2 . . . . -178.7(4) ?
C4 C5 C6 O2 . . . . -0.5(6) ?
C2 O2 C6 C5 . . . . 7.3(6) ?
C6 C5 C7 O5 . . . . -177.5(4) ?
C4 C5 C7 O5 . . . . 4.2(6) ?
C6 C5 C7 C8 . . . . 4.0(6) ?
C4 C5 C7 C8 . . . . -174.2(4) ?
C15 C10 C11 C12 . . . . -1.5(8) ?
C9 C10 C11 C12 . . . . 177.9(5) ?
C10 C11 C12 C13 . . . . 0.5(10) ?
C11 C12 C13 C14 . . . . -0.5(9) ?
C11 C12 C13 C16 . . . . -179.1(6) ?
C12 C13 C14 C15 . . . . 1.7(8) ?
C16 C13 C14 C15 . . . . -179.7(6) ?
C13 C14 C15 C10 . . . . -2.8(8) ?
C11 C10 C15 C14 . . . . 2.7(8) ?
C9 C10 C15 C14 . . . . -176.8(5) ?
C6' O2' C2' C1' . . . . 99.8(4) ?
C6' O2' C2' C3' . . . . -31.4(5) ?
O1' C1' C2' O2' . . . . -69.2(4) ?
O1' C1' C2' C3' . . . . 59.2(5) ?
O2' C2' C3' O3' . . . . -69.1(4) ?
C1' C2' C3' O3' . . . . 163.8(3) ?
O2' C2' C3' C4' . . . . 50.7(4) ?
C1' C2' C3' C4' . . . . -76.4(5) ?
O3' C3' C4' O4' . . . . -160.5(3) ?
C2' C3' C4' O4' . . . . 81.8(4) ?
O3' C3' C4' C5' . . . . 74.3(4) ?
C2' C3' C4' C5' . . . . -43.4(4) ?
O4' C4' C5' C6' . . . . -105.8(4) ?
C3' C4' C5' C6' . . . . 19.2(5) ?
O4' C4' C5' C7' . . . . 73.4(4) ?
C3' C4' C5' C7' . . . . -161.6(3) ?
C7' C5' C6' O2' . . . . -179.7(4) ?
C4' C5' C6' O2' . . . . -0.5(6) ?
C2' O2' C6' C5' . . . . 6.9(6) ?
C6' C5' C7' O5' . . . . -176.8(4) ?
C4' C5' C7' O5' . . . . 4.0(6) ?
C6' C5' C7' C8' . . . . 5.3(6) ?
C4' C5' C7' C8' . . . . -173.9(4) ?
C15' C10' C11' C12' . . . . 0.4(8) ?
C9' C10' C11' C12' . . . . -177.4(5) ?
C10' C11' C12' C13' . . . . 1.5(10) ?
C11' C12' C13' C14' . . . . -1.3(10) ?
C11' C12' C13' C16' . . . . 177.4(7) ?
C12' C13' C14' C15' . . . . -0.8(10) ?
C16' C13' C14' C15' . . . . -179.5(7) ?
C11' C10' C15' C14' . . . . -2.4(8) ?
C9' C10' C15' C14' . . . . 175.3(5) ?
C13' C14' C15' C10' . . . . 2.7(10) ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
O1' H1O' O3' 2_657 0.86(3) 1.78(3) 2.633(4) 176.(7) ?
O3' H3O' O4' 2_747 0.82(3) 1.87(3) 2.664(4) 162.(5) ?
O4' H4O' O1' . 0.85(3) 1.81(3) 2.639(4) 165.(5) ?
O1 H1O O3 2_646 0.83(3) 1.82(3) 2.643(4) 172.(6) ?
O3 H3O O4 2_756 0.82(3) 1.87(3) 2.652(4) 159.(6) ?



# FCF file included here

_shelx_title                     ' RB_USP_HS_MD01_02_Cu_0m_a.res in P2(1)'
_shelx_refln_list_code           4
_shelx_F_calc_maximum            124.23
_reflns_d_resolution_high        0.8094


_shelx_F_squared_multiplier      1.000
