# Electronic Supplementary Material (ESI) for Polymer Chemistry.
# This journal is © The Royal Society of Chemistry 2023

####################################################################### 
# 
# 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_1
_database_code_depnum_ccdc_archive 'CCDC 2094967'
loop_
_audit_author_name
_audit_author_address
'Benjamin Ward'
;Cardiff University
United Kingdom
;
_audit_update_record             
;
2021-07-07 deposited with the CCDC.	2023-04-03 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C20 H20 N2 O3'
_chemical_formula_weight         336.38

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'
N N 0.0061 0.0033 '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      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_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'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, y-1/2, z'

_cell_length_a                   12.782(3)
_cell_length_b                   7.6564(15)
_cell_length_c                   32.715(7)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3201.5(11)
_cell_formula_units_Z            8
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    16425
_cell_measurement_theta_min      2.0170
_cell_measurement_theta_max      31.1670

_exptl_crystal_description       plate
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.396
_exptl_crystal_F_000             1424
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.180
_exptl_crystal_size_mid          0.080
_exptl_crystal_size_min          0.020
_exptl_absorpt_coefficient_mu    0.095
_shelx_estimated_absorpt_T_min   0.983
_shelx_estimated_absorpt_T_max   0.998
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.82305
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.89a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_measurement_device_type  'XtaLAB AFC12 (RCD3): Kappa single'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_reflns_number            43523
_diffrn_reflns_av_unetI/netI     0.0167
_diffrn_reflns_av_R_equivalents  0.0280
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -47
_diffrn_reflns_limit_l_max       47
_diffrn_reflns_theta_min         2.022
_diffrn_reflns_theta_max         32.669
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.888
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.888
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.888
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             5218
_reflns_number_gt                4563
_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       'CrysAlisPro 1.171.41.89a (Rigaku OD, 2020)'
_computing_cell_refinement       'CrysAlisPro 1.171.41.89a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.41.89a (Rigaku OD, 2020)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          
;
The epoxide group was found to be disordered. This region was
modelled over two sites. 
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0851P)²+2.8228P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5218
_refine_ls_number_parameters     263
_refine_ls_number_restraints     138
_refine_ls_R_factor_all          0.0870
_refine_ls_R_factor_gt           0.0764
_refine_ls_wR_factor_ref         0.2115
_refine_ls_wR_factor_gt          0.2052
_refine_ls_goodness_of_fit_ref   1.187
_refine_ls_restrained_S_all      1.181
_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 0.42381(15) 0.7491(3) 0.52391(5) 0.0497(5) Uani 1 1 d . . . . .
C1 C 0.39736(17) 0.7074(3) 0.55840(7) 0.0342(4) Uani 1 1 d D . . . .
N1 N 0.47307(13) 0.6800(2) 0.58850(6) 0.0308(4) Uani 1 1 d . . . . .
N2 N 0.02536(11) 0.52978(19) 0.67406(4) 0.0214(3) Uani 1 1 d . . . . .
O2 O 0.52472(11) 0.59066(19) 0.65143(5) 0.0333(3) Uani 1 1 d . . . . .
C2 C 0.45246(14) 0.6186(2) 0.62793(6) 0.0262(4) Uani 1 1 d D . . . .
C3 C 0.34218(13) 0.5900(2) 0.63872(5) 0.0219(3) Uani 1 1 d . . . . .
C5 C 0.21221(14) 0.5022(2) 0.68864(5) 0.0225(3) Uani 1 1 d . . . . .
H5 H 0.197022 0.457058 0.715037 0.027 Uiso 1 1 calc R U . . .
C4 C 0.31664(14) 0.5251(2) 0.67672(5) 0.0234(3) Uani 1 1 d . . . . .
H4 H 0.371010 0.495260 0.695244 0.028 Uiso 1 1 calc R U . . .
C6 C 0.13052(13) 0.5445(2) 0.66238(5) 0.0196(3) Uani 1 1 d . . . . .
C7 C 0.15491(13) 0.5994(2) 0.62134(5) 0.0210(3) Uani 1 1 d . . . . .
C9 C 0.10463(18) 0.6752(3) 0.55183(6) 0.0375(5) Uani 1 1 d . . . . .
H9 H 0.051716 0.690384 0.531750 0.045 Uiso 1 1 calc R U . . .
C8 C 0.07805(15) 0.6206(3) 0.59055(6) 0.0277(4) Uani 1 1 d . . . . .
H8 H 0.006855 0.596664 0.596730 0.033 Uiso 1 1 calc R U . . .
C10 C 0.20971(18) 0.7087(3) 0.54187(6) 0.0379(5) Uani 1 1 d . . . . .
H10 H 0.227344 0.749949 0.515362 0.046 Uiso 1 1 calc R U . . .
C11 C 0.28687(16) 0.6820(3) 0.57035(6) 0.0283(4) Uani 1 1 d . . . . .
C12 C 0.26152(14) 0.6252(2) 0.61044(5) 0.0218(3) Uani 1 1 d . . . . .
C13 C -0.03640(15) 0.6927(2) 0.67215(6) 0.0262(4) Uani 1 1 d . . . . .
H13A H -0.016323 0.760097 0.647544 0.031 Uiso 1 1 calc R U . . .
H13B H -0.021380 0.765235 0.696500 0.031 Uiso 1 1 calc R U . . .
C14 C -0.15277(15) 0.6504(3) 0.67056(6) 0.0297(4) Uani 1 1 d . . . . .
H14A H -0.193691 0.759973 0.668895 0.036 Uiso 1 1 calc R U . . .
H14B H -0.168161 0.579869 0.645919 0.036 Uiso 1 1 calc R U . . .
C15 C -0.18396(15) 0.5492(3) 0.70873(6) 0.0287(4) Uani 1 1 d . . . . .
H15A H -0.258132 0.512997 0.706664 0.034 Uiso 1 1 calc R U . . .
H15B H -0.176383 0.624787 0.733100 0.034 Uiso 1 1 calc R U . . .
C16 C -0.11447(15) 0.3880(3) 0.71325(6) 0.0267(4) Uani 1 1 d . . . . .
H16A H -0.130855 0.304445 0.691070 0.032 Uiso 1 1 calc R U . . .
H16B H -0.130130 0.330212 0.739621 0.032 Uiso 1 1 calc R U . . .
C17 C 0.00201(14) 0.4335(3) 0.71167(5) 0.0247(3) Uani 1 1 d . . . . .
H17A H 0.020841 0.505612 0.735687 0.030 Uiso 1 1 calc R U . . .
H17B H 0.044083 0.325031 0.712575 0.030 Uiso 1 1 calc R U . . .
O3 O 0.7333(3) 0.5258(8) 0.55242(12) 0.0444(8) Uani 0.789(5) 1 d D U P A 1
C18 C 0.5834(3) 0.7112(7) 0.57706(19) 0.0398(11) Uani 0.789(5) 1 d D U P A 1
H18A H 0.626730 0.725544 0.601927 0.048 Uiso 0.789(5) 1 calc R U P A 1
H18B H 0.589122 0.819076 0.560517 0.048 Uiso 0.789(5) 1 calc R U P A 1
C19 C 0.6223(2) 0.5519(4) 0.55196(9) 0.0346(6) Uani 0.789(5) 1 d D U P A 1
H19 H 0.584916 0.526254 0.525779 0.041 Uiso 0.789(5) 1 calc R U P A 1
C20 C 0.6637(3) 0.4051(5) 0.57413(11) 0.0482(9) Uani 0.789(5) 1 d D . P A 1
H20A H 0.653353 0.287175 0.562375 0.058 Uiso 0.789(5) 1 calc R U P A 1
H20B H 0.662594 0.410241 0.604366 0.058 Uiso 0.789(5) 1 calc R U P A 1
O3A O 0.7441(12) 0.535(3) 0.5623(6) 0.054(3) Uani 0.211(5) 1 d D U P A 2
C18A C 0.5835(10) 0.696(3) 0.5742(6) 0.035(3) Uani 0.211(5) 1 d D U P A 2
H18C H 0.616889 0.796158 0.588118 0.043 Uiso 0.211(5) 1 calc R U P A 2
H18D H 0.583634 0.720370 0.544438 0.043 Uiso 0.211(5) 1 calc R U P A 2
C19A C 0.6484(8) 0.5304(14) 0.5823(3) 0.0365(18) Uani 0.211(5) 1 d D U P A 2
H19A H 0.640334 0.464594 0.608557 0.044 Uiso 0.211(5) 1 calc R U P A 2
C20A C 0.6499(9) 0.4402(18) 0.5440(4) 0.047(2) Uani 0.211(5) 1 d D U P A 2
H20C H 0.613678 0.494443 0.520496 0.057 Uiso 0.211(5) 1 calc R U P A 2
H20D H 0.649922 0.310894 0.544397 0.057 Uiso 0.211(5) 1 calc R U P A 2


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C1 1.220(3) . ?
C1 N1 1.396(3) . ?
C1 C11 1.478(3) . ?
N1 C2 1.398(3) . ?
N1 C18 1.479(4) . ?
N1 C18A 1.492(13) . ?
N2 C6 1.402(2) . ?
N2 C17 1.465(2) . ?
N2 C13 1.477(2) . ?
O2 C2 1.221(2) . ?
C2 C3 1.470(2) . ?
C3 C4 1.378(3) . ?
C3 C12 1.411(2) . ?
C5 C6 1.391(2) . ?
C5 C4 1.402(2) . ?
C6 C7 1.441(2) . ?
C7 C8 1.416(2) . ?
C7 C12 1.422(2) . ?
C9 C8 1.377(3) . ?
C9 C10 1.406(3) . ?
C10 C11 1.372(3) . ?
C11 C12 1.419(2) . ?
C13 C14 1.523(3) . ?
C14 C15 1.523(3) . ?
C15 C16 1.528(3) . ?
C16 C17 1.530(3) . ?
O3 C19 1.433(5) . ?
O3 C20 1.466(5) . ?
C18 C19 1.552(6) . ?
C19 C20 1.439(4) . ?
O3A C19A 1.388(15) . ?
O3A C20A 1.529(15) . ?
C18A C19A 1.538(16) . ?
C19A C20A 1.431(13) . ?

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
O1 C1 N1 119.9(2) . . ?
O1 C1 C11 122.9(2) . . ?
N1 C1 C11 117.13(18) . . ?
C1 N1 C2 124.78(17) . . ?
C1 N1 C18 117.3(3) . . ?
C2 N1 C18 117.9(3) . . ?
C1 N1 C18A 114.9(8) . . ?
C2 N1 C18A 119.7(7) . . ?
C6 N2 C17 117.70(14) . . ?
C6 N2 C13 115.65(14) . . ?
C17 N2 C13 110.57(14) . . ?
O2 C2 N1 119.84(17) . . ?
O2 C2 C3 123.24(18) . . ?
N1 C2 C3 116.91(17) . . ?
C4 C3 C12 119.17(16) . . ?
C4 C3 C2 119.86(16) . . ?
C12 C3 C2 120.96(16) . . ?
C6 C5 C4 120.92(16) . . ?
C3 C4 C5 121.46(16) . . ?
C5 C6 N2 122.18(15) . . ?
C5 C6 C7 118.77(16) . . ?
N2 C6 C7 119.01(15) . . ?
C8 C7 C12 118.04(16) . . ?
C8 C7 C6 123.09(16) . . ?
C12 C7 C6 118.79(15) . . ?
C8 C9 C10 120.30(19) . . ?
C9 C8 C7 121.20(18) . . ?
C11 C10 C9 120.15(19) . . ?
C10 C11 C12 120.60(18) . . ?
C10 C11 C1 119.19(18) . . ?
C12 C11 C1 120.18(18) . . ?
C3 C12 C11 119.85(17) . . ?
C3 C12 C7 120.57(15) . . ?
C11 C12 C7 119.55(16) . . ?
N2 C13 C14 110.11(15) . . ?
C15 C14 C13 109.62(16) . . ?
C14 C15 C16 109.78(15) . . ?
C15 C16 C17 112.25(16) . . ?
N2 C17 C16 109.96(15) . . ?
C19 O3 C20 59.5(2) . . ?
N1 C18 C19 108.2(4) . . ?
O3 C19 C20 61.4(3) . . ?
O3 C19 C18 114.9(3) . . ?
C20 C19 C18 117.7(3) . . ?
C19 C20 O3 59.1(3) . . ?
C19A O3A C20A 58.5(7) . . ?
N1 C18A C19A 112.8(12) . . ?
O3A C19A C20A 65.7(8) . . ?
O3A C19A C18A 111.7(15) . . ?
C20A C19A C18A 104.6(13) . . ?
C19A C20A O3A 55.8(7) . . ?

_refine_diff_density_max         0.485
_refine_diff_density_min         -0.423
_refine_diff_density_rms         0.066

_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: DCM, petroleum ether'
####################################################################### 
# 
# 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_2
_database_code_depnum_ccdc_archive 'CCDC 2094968'
loop_
_audit_author_name
_audit_author_address
'Benjamin Ward'
;Cardiff University
United Kingdom
;
_audit_update_record             
;
2021-07-07 deposited with the CCDC.	2023-04-03 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C17 H13 N O3'
_chemical_formula_weight         279.28

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'
N N 0.0061 0.0033 '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      trigonal
_space_group_IT_number           148
_space_group_name_H-M_alt        'R -3 :H'
_space_group_name_Hall           '-R 3'

_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'
'-y, x-y, z'
'-x+y, -x, z'
'x+2/3, y+1/3, z+1/3'
'-y+2/3, x-y+1/3, z+1/3'
'-x+y+2/3, -x+1/3, z+1/3'
'x+1/3, y+2/3, z+2/3'
'-y+1/3, x-y+2/3, z+2/3'
'-x+y+1/3, -x+2/3, z+2/3'
'-x, -y, -z'
'y, -x+y, -z'
'x-y, x, -z'
'-x+2/3, -y+1/3, -z+1/3'
'y+2/3, -x+y+1/3, -z+1/3'
'x-y+2/3, x+1/3, -z+1/3'
'-x+1/3, -y+2/3, -z+2/3'
'y+1/3, -x+y+2/3, -z+2/3'
'x-y+1/3, x+2/3, -z+2/3'

_cell_length_a                   29.6286(6)
_cell_length_b                   29.6286(6)
_cell_length_c                   7.6747(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_volume                     5834.6(3)
_cell_formula_units_Z            18
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    6933
_cell_measurement_theta_min      2.3930
_cell_measurement_theta_max      29.8330

_exptl_crystal_description       '(cut) block'
_exptl_crystal_colour            red
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.431
_exptl_crystal_F_000             2628
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.058
_exptl_crystal_size_min          0.020
_exptl_absorpt_coefficient_mu    0.099
_shelx_estimated_absorpt_T_min   0.971
_shelx_estimated_absorpt_T_max   0.998
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_correction_T_min  0.792
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.68a (Rigaku Oxford Diffraction, 2019)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_measurement_device_type  'XtaLAB AFC12 (RCD3): Kappa single'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_reflns_number            33544
_diffrn_reflns_av_unetI/netI     0.0270
_diffrn_reflns_av_R_equivalents  0.0710
_diffrn_reflns_limit_h_min       -38
_diffrn_reflns_limit_h_max       38
_diffrn_reflns_limit_k_min       -38
_diffrn_reflns_limit_k_max       38
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         2.381
_diffrn_reflns_theta_max         27.481
_diffrn_reflns_theta_full        25.242
_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             2976
_reflns_number_gt                2303
_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       'CrysAlisPro 1.171.40.68a (Rigaku OD, 2019)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.68a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.68a (Rigaku OD, 2019)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          
;
The epoxide part of the molecule was disordered. This region was modelled
as two-site disorder. The N-H was located in the Fourier difference map
and its position refined with the N-H distance restrained to 0.88 Å and
Uiso fixed at 1.2 Ueq(N).
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1350P)²+3.7120P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2976
_refine_ls_number_parameters     230
_refine_ls_number_restraints     103
_refine_ls_R_factor_all          0.0799
_refine_ls_R_factor_gt           0.0668
_refine_ls_wR_factor_ref         0.2181
_refine_ls_wR_factor_gt          0.2022
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_restrained_S_all      1.134
_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 0.5989(3) 0.3052(3) 0.6394(11) 0.157(3) Uani 0.452(8) 1 d D U P A 1
C1 C 0.5662(5) 0.2550(6) 0.545(2) 0.131(4) Uani 0.452(8) 1 d D U P A 1
H1A H 0.584476 0.243203 0.464912 0.157 Uiso 0.452(8) 1 calc R U P A 1
H1B H 0.537147 0.226520 0.610178 0.157 Uiso 0.452(8) 1 calc R U P A 1
C2 C 0.5605(6) 0.2867(6) 0.499(2) 0.141(4) Uani 0.452(8) 1 d D U P A 1
H2 H 0.574625 0.300542 0.380645 0.170 Uiso 0.452(8) 1 calc R U P A 1
C3 C 0.5178(7) 0.3035(8) 0.579(3) 0.137(5) Uani 0.452(8) 1 d . U P A 1
H3A H 0.519166 0.305101 0.707912 0.164 Uiso 0.452(8) 1 calc R U P A 1
H3B H 0.525229 0.337764 0.533021 0.164 Uiso 0.452(8) 1 calc R U P A 1
O1A O 0.5542(2) 0.2553(3) 0.6532(9) 0.142(3) Uani 0.548(8) 1 d D U P A 2
C1A C 0.5581(3) 0.2613(4) 0.4615(9) 0.096(2) Uani 0.548(8) 1 d D U P A 2
H1AA H 0.591466 0.269472 0.405501 0.115 Uiso 0.548(8) 1 calc R U P A 2
H1AB H 0.526497 0.239516 0.391340 0.115 Uiso 0.548(8) 1 calc R U P A 2
C2A C 0.5579(2) 0.3000(3) 0.5770(9) 0.0855(18) Uani 0.548(8) 1 d D U P A 2
H2A H 0.592437 0.332377 0.591655 0.103 Uiso 0.548(8) 1 calc R U P A 2
C3A C 0.5135(2) 0.3084(4) 0.5655(11) 0.0660(17) Uani 0.548(8) 1 d . U P A 2
H3A1 H 0.508392 0.320844 0.679427 0.079 Uiso 0.548(8) 1 calc R U P A 2
H3A2 H 0.520994 0.335750 0.477843 0.079 Uiso 0.548(8) 1 calc R U P A 2
O2 O 0.41766(6) 0.16839(6) 0.36694(19) 0.0582(4) Uani 1 1 d . . . . .
O3 O 0.23195(6) 0.15655(5) 0.46914(19) 0.0553(4) Uani 1 1 d . . . . .
N1 N 0.46589(7) 0.26105(8) 0.5173(3) 0.0616(5) Uani 1 1 d D . . . .
H1N H 0.4677(11) 0.2378(9) 0.450(3) 0.074 Uiso 1 1 d D U . . .
C4 C 0.41833(8) 0.25578(8) 0.5364(2) 0.0491(5) Uani 1 1 d . . . . .
C5 C 0.41213(8) 0.29577(7) 0.6153(2) 0.0514(5) Uani 1 1 d . . . . .
H5 H 0.442052 0.326869 0.653062 0.062 Uiso 1 1 calc R U . . .
C6 C 0.36382(8) 0.29021(7) 0.6376(2) 0.0505(5) Uani 1 1 d . . . . .
H6 H 0.360775 0.317484 0.691046 0.061 Uiso 1 1 calc R U . . .
C7 C 0.31919(8) 0.24548(7) 0.5837(2) 0.0458(4) Uani 1 1 d . . . . .
H7 H 0.285843 0.241976 0.601355 0.055 Uiso 1 1 calc R U . . .
C8 C 0.32367(7) 0.20594(7) 0.5038(2) 0.0413(4) Uani 1 1 d . . . . .
C9 C 0.27436(7) 0.15973(7) 0.4458(2) 0.0442(4) Uani 1 1 d . . . . .
C10 C 0.27811(8) 0.11754(7) 0.3547(2) 0.0456(4) Uani 1 1 d . . . . .
C11 C 0.23275(9) 0.07391(7) 0.2937(3) 0.0562(5) Uani 1 1 d . . . . .
H11 H 0.199734 0.071195 0.311106 0.067 Uiso 1 1 calc R U . . .
C12 C 0.23636(11) 0.03463(8) 0.2075(3) 0.0630(6) Uani 1 1 d . . . . .
H12 H 0.205712 0.004798 0.166440 0.076 Uiso 1 1 calc R U . . .
C13 C 0.28438(11) 0.03889(8) 0.1814(3) 0.0640(7) Uani 1 1 d . . . . .
H13 H 0.286528 0.011937 0.121693 0.077 Uiso 1 1 calc R U . . .
C14 C 0.32934(10) 0.08170(8) 0.2408(2) 0.0564(6) Uani 1 1 d . . . . .
H14 H 0.362154 0.084104 0.221730 0.068 Uiso 1 1 calc R U . . .
C15 C 0.32667(8) 0.12162(7) 0.3293(2) 0.0463(5) Uani 1 1 d . . . . .
C16 C 0.37565(8) 0.16736(7) 0.3914(2) 0.0459(4) Uani 1 1 d . . . . .
C17 C 0.37276(7) 0.20975(7) 0.4785(2) 0.0431(4) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C2 1.458(12) . ?
O1 C1 1.497(12) . ?
C1 C2 1.090(19) . ?
C2 C3 1.69(3) . ?
C3 N1 1.496(18) . ?
O1A C2A 1.399(9) . ?
O1A C1A 1.479(9) . ?
C1A C2A 1.451(10) . ?
C2A C3A 1.459(10) . ?
C3A N1 1.454(7) . ?
O2 C16 1.244(2) . ?
O3 C9 1.225(2) . ?
N1 C4 1.346(3) . ?
C4 C5 1.422(3) . ?
C4 C17 1.428(3) . ?
C5 C6 1.367(3) . ?
C6 C7 1.387(3) . ?
C7 C8 1.386(2) . ?
C8 C17 1.415(2) . ?
C8 C9 1.485(3) . ?
C9 C10 1.484(2) . ?
C10 C15 1.396(3) . ?
C10 C11 1.400(3) . ?
C11 C12 1.388(3) . ?
C12 C13 1.379(4) . ?
C13 C14 1.379(3) . ?
C14 C15 1.400(3) . ?
C15 C16 1.484(3) . ?
C16 C17 1.463(2) . ?

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 O1 C1 43.3(8) . . ?
C2 C1 O1 66.4(9) . . ?
C1 C2 O1 70.3(9) . . ?
C1 C2 C3 127(2) . . ?
O1 C2 C3 100.4(14) . . ?
N1 C3 C2 104.2(13) . . ?
C2A O1A C1A 60.5(5) . . ?
C2A C1A O1A 57.0(4) . . ?
O1A C2A C1A 62.5(5) . . ?
O1A C2A C3A 122.4(7) . . ?
C1A C2A C3A 117.3(6) . . ?
N1 C3A C2A 111.9(7) . . ?
C4 N1 C3A 122.6(4) . . ?
C4 N1 C3 129.8(8) . . ?
N1 C4 C5 120.91(18) . . ?
N1 C4 C17 120.81(19) . . ?
C5 C4 C17 118.28(17) . . ?
C6 C5 C4 121.11(17) . . ?
C5 C6 C7 121.22(18) . . ?
C8 C7 C6 119.39(18) . . ?
C7 C8 C17 121.49(17) . . ?
C7 C8 C9 116.45(16) . . ?
C17 C8 C9 122.06(15) . . ?
O3 C9 C10 120.65(17) . . ?
O3 C9 C8 121.70(16) . . ?
C10 C9 C8 117.64(16) . . ?
C15 C10 C11 120.36(18) . . ?
C15 C10 C9 120.06(17) . . ?
C11 C10 C9 119.58(18) . . ?
C12 C11 C10 119.5(2) . . ?
C13 C12 C11 120.1(2) . . ?
C12 C13 C14 120.94(19) . . ?
C13 C14 C15 120.1(2) . . ?
C10 C15 C14 119.07(19) . . ?
C10 C15 C16 121.94(15) . . ?
C14 C15 C16 118.99(18) . . ?
O2 C16 C17 122.36(18) . . ?
O2 C16 C15 118.92(17) . . ?
C17 C16 C15 118.73(16) . . ?
C8 C17 C4 118.49(16) . . ?
C8 C17 C16 119.55(16) . . ?
C4 C17 C16 121.94(17) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
N1 H1N O2 0.886(17) 1.94(2) 2.643(3) 135(2) . yes

_refine_diff_density_max         0.316
_refine_diff_density_min         -0.332
_refine_diff_density_rms         0.058

_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: DCM, petroleum ether'
####################################################################### 
# 
# 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_cyclohexanediol
_database_code_depnum_ccdc_archive 'CCDC 2094969'
loop_
_audit_author_name
_audit_author_address
'Benjamin Ward'
;Cardiff University
United Kingdom
;
_audit_update_record             
;
2021-07-07 deposited with the CCDC.	2023-04-03 downloaded from the CCDC.
;
_audit_creation_date             2021-06-04
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C6 H12 O2'
_chemical_formula_sum            'C6 H12 O2'
_chemical_formula_weight         116.16
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   18.6396(18)
_cell_length_b                   9.9559(7)
_cell_length_c                   7.3000(6)
_cell_angle_alpha                90
_cell_angle_beta                 96.583(7)
_cell_angle_gamma                90
_cell_volume                     1345.8(2)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    1852
_cell_measurement_temperature    296
_cell_measurement_theta_max      76.0940
_cell_measurement_theta_min      4.7600
_shelx_estimated_absorpt_T_max   0.930
_shelx_estimated_absorpt_T_min   0.817
_exptl_absorpt_coefficient_mu    0.687
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.607
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.82a (Rigaku Oxford Diffraction, 2020)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.147
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             512
_exptl_crystal_size_max          0.306
_exptl_crystal_size_mid          0.113
_exptl_crystal_size_min          0.107
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0164
_diffrn_reflns_av_unetI/netI     0.0118
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            6179
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.481
_diffrn_reflns_theta_min         4.776
_diffrn_ambient_temperature      296
_diffrn_detector_area_resol_mean 10.5082
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near ATLAS'
_diffrn_measurement_method       ?
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1133
_reflns_number_total             1412
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_data_collection       'CrysAlisPro 1.171.40.82a (Rigaku OD, 2020)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.82a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.40.82a (Rigaku OD, 2020)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.090
_refine_diff_density_min         -0.118
_refine_diff_density_rms         0.029
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.064
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     150
_refine_ls_number_reflns         1412
_refine_ls_number_restraints     316
_refine_ls_R_factor_all          0.0472
_refine_ls_R_factor_gt           0.0397
_refine_ls_restrained_S_all      1.034
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0663P)²+0.1534P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1183
_refine_ls_wR_factor_ref         0.1275
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All O(H) groups
2. Restrained distances
 C1A-C2A = C2A-C3A = C3A-C4A = C4A-C5A = C5A-C6A = C6A-C1A
 1.54 with sigma of 0.02
 C1-C2 = C2-C3 = C3-C4 = C4-C5 = C5-C6 = C6-C1
 1.54 with sigma of 0.02
 C1-O1 = C2-O2 = C1A-O1A = C2A-O2A
 1.43 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
O1 \\sim O2 \\sim C1 \\sim C2 \\sim C3 \\sim C4 \\sim C5 \\sim C6 \\sim O1A
\\sim O2A \\sim C1A \\sim C2A \\sim C3A \\sim C4A \\sim C5A: within 2A with
sigma of 0.01 and sigma for terminal atoms of 0.02 within 2A
Uanis(O1A) \\sim Ueq, Uanis(O2A) \\sim Ueq, Uanis(C1A) \\sim Ueq, Uanis(C2A)
\\sim Ueq, Uanis(C3A) \\sim Ueq, Uanis(C4A) \\sim Ueq, Uanis(C5A) \\sim Ueq:
with sigma of 0.05 and sigma for terminal atoms of 0.1
Uanis(O1) \\sim Ueq, Uanis(O2) \\sim Ueq, Uanis(C1) \\sim Ueq, Uanis(C2) \\sim
Ueq, Uanis(C3) \\sim Ueq, Uanis(C4) \\sim Ueq, Uanis(C5) \\sim Ueq, Uanis(C6)
\\sim Ueq: with sigma of 0.05 and sigma for terminal atoms of 0.1
4. Others
 Sof(O1A)=Sof(H1AA)=Sof(O2A)=Sof(H2AA)=Sof(C1A)=Sof(H1AB)=Sof(C2A)=Sof(H2AB)=
 Sof(C3A)=Sof(H3AA)=Sof(H3AB)=Sof(C4A)=Sof(H4AA)=Sof(H4AB)=Sof(C5A)=Sof(H5AA)=
 Sof(H5AB)=Sof(C6A)=Sof(H6AA)=Sof(H6AB)=1-FVAR(1)
 Sof(O1)=Sof(H1)=Sof(O2)=Sof(H2)=Sof(C1)=Sof(H1A)=Sof(C2)=Sof(H2A)=Sof(C3)=
 Sof(H3A)=Sof(H3B)=Sof(C4)=Sof(H4A)=Sof(H4B)=Sof(C5)=Sof(H5A)=Sof(H5B)=Sof(C6)=
 Sof(H6A)=Sof(H6B)=FVAR(1)
5.a Ternary CH refined with riding coordinates:
 C1(H1A), C2(H2A), C1A(H1AB), C2A(H2AB)
5.b Secondary CH2 refined with riding coordinates:
 C3(H3A,H3B), C4(H4A,H4B), C5(H5A,H5B), C6(H6A,H6B), C3A(H3AA,H3AB), C4A(H4AA,
 H4AB), C5A(H5AA,H5AB), C6A(H6AA,H6AB)
5.c Idealised tetrahedral OH refined as rotating group:
 O1(H1), O2(H2), O1A(H1AA), O2A(H2AA)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
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 0.2594(2) 0.6158(4) 0.2299(6) 0.0861(11) Uani 0.858(3) 1 d D U P A 1
H1 H 0.243267 0.628362 0.121956 0.129 Uiso 0.858(3) 1 calc R U P A 1
O2 O 0.28986(19) 0.8863(4) 0.1427(4) 0.0790(9) Uani 0.858(3) 1 d D U P A 1
H2 H 0.271942 0.957567 0.170773 0.119 Uiso 0.858(3) 1 calc R U P A 1
C1 C 0.32922(8) 0.67494(14) 0.26438(19) 0.0637(4) Uani 0.858(3) 1 d D U P A 1
H1A H 0.355196 0.661830 0.156383 0.076 Uiso 0.858(3) 1 calc R U P A 1
C2 C 0.32478(8) 0.82337(13) 0.30434(19) 0.0605(4) Uani 0.858(3) 1 d D U P A 1
H2A H 0.295011 0.836182 0.405233 0.073 Uiso 0.858(3) 1 calc R U P A 1
C3 C 0.39846(19) 0.8827(4) 0.3606(5) 0.0784(10) Uani 0.858(3) 1 d D U P A 1
H3A H 0.393367 0.976992 0.390021 0.094 Uiso 0.858(3) 1 calc R U P A 1
H3B H 0.427128 0.876575 0.258118 0.094 Uiso 0.858(3) 1 calc R U P A 1
C4 C 0.43743(13) 0.8107(2) 0.5266(3) 0.0899(7) Uani 0.858(3) 1 d D U P A 1
H4A H 0.411582 0.824619 0.633025 0.108 Uiso 0.858(3) 1 calc R U P A 1
H4B H 0.485624 0.847529 0.554435 0.108 Uiso 0.858(3) 1 calc R U P A 1
C5 C 0.44233(9) 0.6605(2) 0.4875(3) 0.0922(6) Uani 0.858(3) 1 d D U P A 1
H5A H 0.473365 0.646399 0.391275 0.111 Uiso 0.858(3) 1 calc R U P A 1
H5B H 0.463874 0.614963 0.597753 0.111 Uiso 0.858(3) 1 calc R U P A 1
C6 C 0.36844(16) 0.6006(3) 0.4276(3) 0.0791(7) Uani 0.858(3) 1 d D U P A 1
H6A H 0.374002 0.507103 0.394624 0.095 Uiso 0.858(3) 1 calc R U P A 1
H6B H 0.339602 0.603867 0.529956 0.095 Uiso 0.858(3) 1 calc R U P A 1
O1A O 0.2517(11) 0.644(2) 0.233(3) 0.070(3) Uani 0.142(3) 1 d D U P A 2
H1AA H 0.248727 0.671781 0.126580 0.104 Uiso 0.142(3) 1 calc R U P A 2
O2A O 0.3041(9) 0.8775(17) 0.103(2) 0.065(3) Uani 0.142(3) 1 d D U P A 2
H2AA H 0.286898 0.937672 0.160767 0.097 Uiso 0.142(3) 1 calc R U P A 2
C1A C 0.3067(5) 0.7208(8) 0.3467(12) 0.0657(18) Uani 0.142(3) 1 d D U P A 2
H1AB H 0.282108 0.786016 0.418436 0.079 Uiso 0.142(3) 1 calc R U P A 2
C2A C 0.3500(5) 0.7955(9) 0.2262(13) 0.0662(18) Uani 0.142(3) 1 d D U P A 2
H2AB H 0.373085 0.729839 0.151813 0.079 Uiso 0.142(3) 1 calc R U P A 2
C3A C 0.4094(13) 0.877(2) 0.333(3) 0.071(3) Uani 0.142(3) 1 d D U P A 2
H3AA H 0.388479 0.949411 0.397816 0.086 Uiso 0.142(3) 1 calc R U P A 2
H3AB H 0.440163 0.916000 0.248327 0.086 Uiso 0.142(3) 1 calc R U P A 2
C4A C 0.4548(8) 0.7847(16) 0.4726(19) 0.083(2) Uani 0.142(3) 1 d D U P A 2
H4AA H 0.478748 0.716882 0.406007 0.100 Uiso 0.142(3) 1 calc R U P A 2
H4AB H 0.491807 0.837795 0.543592 0.100 Uiso 0.142(3) 1 calc R U P A 2
C5A C 0.4096(5) 0.7180(11) 0.5999(13) 0.086(2) Uani 0.142(3) 1 d D U P A 2
H5AA H 0.384948 0.784667 0.666653 0.103 Uiso 0.142(3) 1 calc R U P A 2
H5AB H 0.439506 0.663468 0.688540 0.103 Uiso 0.142(3) 1 calc R U P A 2
C6A C 0.3552(7) 0.6306(12) 0.4847(17) 0.067(3) Uani 0.142(3) 1 d D . P A 2
H6AA H 0.325473 0.583129 0.564260 0.080 Uiso 0.142(3) 1 calc R U P A 2
H6AB H 0.380154 0.564686 0.417448 0.080 Uiso 0.142(3) 1 calc R U P A 2


_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 H1 0.8200 . ?
O1 C1 1.425(4) . ?
O2 H2 0.8200 . ?
O2 C2 1.426(3) . ?
C1 H1A 0.9800 . ?
C1 C2 1.510(2) . ?
C1 C6 1.517(3) . ?
C2 H2A 0.9800 . ?
C2 C3 1.508(4) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C3 C4 1.519(4) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C4 C5 1.527(3) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C5 C6 1.519(3) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
O1A H1AA 0.8200 . ?
O1A C1A 1.456(15) . ?
O2A H2AA 0.8200 . ?
O2A C2A 1.427(15) . ?
C1A H1AB 0.9800 . ?
C1A C2A 1.464(12) . ?
C1A C6A 1.559(13) . ?
C2A H2AB 0.9800 . ?
C2A C3A 1.513(18) . ?
C3A H3AA 0.9700 . ?
C3A H3AB 0.9700 . ?
C3A C4A 1.550(18) . ?
C4A H4AA 0.9700 . ?
C4A H4AB 0.9700 . ?
C4A C5A 1.481(15) . ?
C5A H5AA 0.9700 . ?
C5A H5AB 0.9700 . ?
C5A C6A 1.516(13) . ?
C6A H6AA 0.9700 . ?
C6A H6AB 0.9700 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 O1 H1 109.5 . . ?
C2 O2 H2 109.5 . . ?
O1 C1 H1A 109.2 . . ?
O1 C1 C2 111.6(2) . . ?
O1 C1 C6 106.6(2) . . ?
C2 C1 H1A 109.2 . . ?
C2 C1 C6 110.96(14) . . ?
C6 C1 H1A 109.2 . . ?
O2 C2 C1 107.46(17) . . ?
O2 C2 H2A 108.7 . . ?
O2 C2 C3 111.6(2) . . ?
C1 C2 H2A 108.7 . . ?
C3 C2 C1 111.56(19) . . ?
C3 C2 H2A 108.7 . . ?
C2 C3 H3A 109.3 . . ?
C2 C3 H3B 109.3 . . ?
C2 C3 C4 111.7(3) . . ?
H3A C3 H3B 107.9 . . ?
C4 C3 H3A 109.3 . . ?
C4 C3 H3B 109.3 . . ?
C3 C4 H4A 109.6 . . ?
C3 C4 H4B 109.6 . . ?
C3 C4 C5 110.3(2) . . ?
H4A C4 H4B 108.1 . . ?
C5 C4 H4A 109.6 . . ?
C5 C4 H4B 109.6 . . ?
C4 C5 H5A 109.3 . . ?
C4 C5 H5B 109.3 . . ?
H5A C5 H5B 108.0 . . ?
C6 C5 C4 111.52(16) . . ?
C6 C5 H5A 109.3 . . ?
C6 C5 H5B 109.3 . . ?
C1 C6 C5 112.0(2) . . ?
C1 C6 H6A 109.2 . . ?
C1 C6 H6B 109.2 . . ?
C5 C6 H6A 109.2 . . ?
C5 C6 H6B 109.2 . . ?
H6A C6 H6B 107.9 . . ?
C1A O1A H1AA 109.5 . . ?
C2A O2A H2AA 109.5 . . ?
O1A C1A H1AB 108.0 . . ?
O1A C1A C2A 108.9(11) . . ?
O1A C1A C6A 112.7(12) . . ?
C2A C1A H1AB 108.0 . . ?
C2A C1A C6A 111.2(8) . . ?
C6A C1A H1AB 108.0 . . ?
O2A C2A C1A 109.7(10) . . ?
O2A C2A H2AB 107.5 . . ?
O2A C2A C3A 111.7(12) . . ?
C1A C2A H2AB 107.5 . . ?
C1A C2A C3A 112.6(12) . . ?
C3A C2A H2AB 107.5 . . ?
C2A C3A H3AA 109.8 . . ?
C2A C3A H3AB 109.8 . . ?
C2A C3A C4A 109.5(16) . . ?
H3AA C3A H3AB 108.2 . . ?
C4A C3A H3AA 109.8 . . ?
C4A C3A H3AB 109.8 . . ?
C3A C4A H4AA 109.3 . . ?
C3A C4A H4AB 109.3 . . ?
H4AA C4A H4AB 107.9 . . ?
C5A C4A C3A 111.8(14) . . ?
C5A C4A H4AA 109.3 . . ?
C5A C4A H4AB 109.3 . . ?
C4A C5A H5AA 110.2 . . ?
C4A C5A H5AB 110.2 . . ?
C4A C5A C6A 107.6(10) . . ?
H5AA C5A H5AB 108.5 . . ?
C6A C5A H5AA 110.2 . . ?
C6A C5A H5AB 110.2 . . ?
C1A C6A H6AA 109.8 . . ?
C1A C6A H6AB 109.8 . . ?
C5A C6A C1A 109.2(8) . . ?
C5A C6A H6AA 109.8 . . ?
C5A C6A H6AB 109.8 . . ?
H6AA C6A H6AB 108.3 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
O1 H1 O2 0.82 1.96 2.769(5) 166.6 7_565 yes
O2 H2 O1 0.82 1.86 2.669(5) 170.8 4 yes
O1A H1AA O2A 0.82 1.91 2.56(3) 136.0 7_565 yes
O2A H2AA O1A 0.82 2.34 3.14(3) 165.1 4 yes

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C1 C2 O2 -63.4(3) . . . . ?
O1 C1 C2 C3 173.9(3) . . . . ?
O1 C1 C6 C5 -176.0(2) . . . . ?
O2 C2 C3 C4 -176.9(2) . . . . ?
C1 C2 C3 C4 -56.6(3) . . . . ?
C2 C1 C6 C5 -54.3(2) . . . . ?
C2 C3 C4 C5 55.8(3) . . . . ?
C3 C4 C5 C6 -54.5(3) . . . . ?
C4 C5 C6 C1 54.4(2) . . . . ?
C6 C1 C2 O2 177.8(2) . . . . ?
C6 C1 C2 C3 55.2(3) . . . . ?
O1A C1A C2A O2A 55.6(17) . . . . ?
O1A C1A C2A C3A -179.3(16) . . . . ?
O1A C1A C6A C5A -178.8(13) . . . . ?
O2A C2A C3A C4A 176.7(15) . . . . ?
C1A C2A C3A C4A 53(2) . . . . ?
C2A C1A C6A C5A 58.6(12) . . . . ?
C2A C3A C4A C5A -57(2) . . . . ?
C3A C4A C5A C6A 61.8(17) . . . . ?
C4A C5A C6A C1A -61.2(14) . . . . ?
C6A C1A C2A O2A -179.6(10) . . . . ?
C6A C1A C2A C3A -54.6(15) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'




_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: ethyl acetate'
