# Electronic Supplementary Material (ESI) for Polymer Chemistry.
# This journal is © The Royal Society of Chemistry 2020

####################################################################### 
# 
# 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_pna21
_database_code_depnum_ccdc_archive 'CCDC 1949075'
loop_
_audit_author_name
_audit_author_address
'Angel Ugrinov and Qianli Rick Chu'
;North Dakota State University and University of North Dakota 
United States of America
;
_audit_update_record             
;
2019-08-24 deposited with the CCDC.	2020-08-18 downloaded from the CCDC.
;
_audit_creation_date             2018-11-21
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2017/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '2(C18 H20 O2)'
_chemical_formula_sum            'C36 H40 O4'
_chemical_formula_weight         536.68
_chemical_absolute_configuration ?
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           33
_space_group_name_H-M_alt        'P n a 21'
_space_group_name_Hall           'P 2c -2n'
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'

_cell_length_a                   17.9616(7)
_cell_length_b                   7.6761(3)
_cell_length_c                   21.5205(9)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2967.1(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9949
_cell_measurement_temperature    110(2)
_cell_measurement_theta_max      66.257
_cell_measurement_theta_min      4.109
_shelx_estimated_absorpt_T_max   0.965
_shelx_estimated_absorpt_T_min   0.805
_exptl_absorpt_coefficient_mu    0.604
_exptl_absorpt_correction_T_max  0.7528
_exptl_absorpt_correction_T_min  0.6693
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0992 before and 0.0634 after correction. The Ratio of minimum to maximum transmission is 0.8891. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.201
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             1152
_exptl_crystal_preparation       ?
_exptl_crystal_size_max          0.375
_exptl_crystal_size_mid          0.121
_exptl_crystal_size_min          0.06
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0967
_diffrn_reflns_av_unetI/netI     0.0308
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            73145
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        66.885
_diffrn_reflns_theta_max         66.885
_diffrn_reflns_theta_min         4.108
_diffrn_ambient_temperature      109.99
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.944
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.998
_reflns_number_gt                4930
_reflns_number_total             5263
_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_cell_refinement       'SAINT V8.38A (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.776
_refine_diff_density_min         -0.250
_refine_diff_density_rms         0.065
_refine_ls_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.2(6)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.082
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     366
_refine_ls_number_reflns         5263
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0825
_refine_ls_R_factor_gt           0.0782
_refine_ls_restrained_S_all      1.082
_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)+(0.1008P)²+4.5988P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2040
_refine_ls_wR_factor_ref         0.2071
_refine_special_details          
;
 Refined as a 2-component inversion twin.
;
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 0.8(6)
 0.2(6)
2. 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
3.a Ternary CH refined with riding coordinates:
 C009(H009), C00B(H00C), C00D(H00F), C00E(H00K), C00I(H00I), C00L(H00L),
 C00N(H00O), C00R(H00T)
3.b Secondary CH2 refined with riding coordinates:
 C006(H00A,H00B), C00C(H00D,H00E), C00M(H00M,H00N), C00P(H00R,H00S)
3.c Aromatic/amide H refined with riding coordinates:
 C007(H007), C008(H008), C00G(H00G), C00H(H00H), C00J(H00J), C00O(H00P),
 C00Q(H00Q), C00S(H00U), C00T(H00V), C00U(H00W), C00V(H00X), C00W(H00Y),
 C00X(H00), C00Y(H0AA), C00Z(H00Z), C010(H010), C011(H011), C012(H012),
 C013(H013), C014(H014)
3.d Idealised tetrahedral OH refined as rotating group:
 O001(H001), O002(H002), O003(H003), O004(H004)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O001 O 0.1741(2) -0.3031(5) 0.94339(19) 0.0312(10) Uani 1 1 d . . . . .
H001 H 0.142165 -0.258952 0.967181 0.047 Uiso 1 1 calc GR . . . .
O002 O 0.4237(2) 0.3591(5) 0.52427(18) 0.0304(9) Uani 1 1 d . . . . .
H002 H 0.421326 0.467070 0.530313 0.046 Uiso 1 1 calc GR . . . .
O003 O 0.2182(2) 0.3612(5) 0.96455(19) 0.0317(9) Uani 1 1 d . . . . .
H003 H 0.203158 0.461556 0.955382 0.048 Uiso 1 1 calc GR . . . .
O004 O 0.3806(3) -0.3007(6) 0.5443(2) 0.0365(10) Uani 1 1 d . . . . .
H004 H 0.344789 -0.334006 0.522250 0.055 Uiso 1 1 calc GR . . . .
C005 C 0.0933(3) 0.1903(7) 0.8601(3) 0.0298(13) Uani 1 1 d . . . . .
C006 C 0.1514(4) -0.2794(7) 0.8803(3) 0.0307(13) Uani 1 1 d . . . . .
H00A H 0.097393 -0.303734 0.877510 0.037 Uiso 1 1 calc R . . . .
H00B H 0.177354 -0.367142 0.854466 0.037 Uiso 1 1 calc R . . . .
C007 C 0.0382(3) 0.2786(8) 0.8925(3) 0.0370(15) Uani 1 1 d . . . . .
H007 H 0.030412 0.253927 0.935283 0.044 Uiso 1 1 calc R . . . .
C008 C 0.1053(3) 0.2363(9) 0.7986(3) 0.0340(14) Uani 1 1 d . . . . .
H008 H 0.143513 0.180262 0.775606 0.041 Uiso 1 1 calc R . . . .
C009 C 0.2466(3) -0.0284(8) 0.8593(3) 0.0306(13) Uani 1 1 d . . . . .
H009 H 0.258162 0.044539 0.822032 0.037 Uiso 1 1 calc R . . . .
C00A C 0.5202(3) -0.1573(8) 0.6129(3) 0.0354(15) Uani 1 1 d . . . . .
C00B C 0.1657(3) -0.1021(7) 0.8527(3) 0.0282(12) Uani 1 1 d . . . . .
H00C H 0.147223 -0.094011 0.808985 0.034 Uiso 1 1 calc R . . . .
C00C C 0.2467(3) 0.2788(8) 0.9106(3) 0.0336(14) Uani 1 1 d . . . . .
H00D H 0.301796 0.281805 0.910747 0.040 Uiso 1 1 calc R . . . .
H00E H 0.228624 0.338650 0.872781 0.040 Uiso 1 1 calc R . . . .
C00D C 0.2191(3) 0.0917(7) 0.9120(3) 0.0271(12) Uani 1 1 d . . . . .
H00F H 0.230691 0.037953 0.953238 0.032 Uiso 1 1 calc R . . . .
C00E C 0.4260(3) 0.0881(8) 0.5766(3) 0.0311(13) Uani 1 1 d . . . . .
H00K H 0.433508 0.034074 0.534823 0.037 Uiso 1 1 calc R . . . .
C00F C 0.3090(3) 0.1983(8) 0.6374(3) 0.0333(14) Uani 1 1 d . . . . .
C00G C 0.0613(4) 0.3649(9) 0.7699(3) 0.0384(15) Uani 1 1 d . . . . .
H00G H 0.070815 0.396546 0.727966 0.046 Uiso 1 1 calc R . . . .
C00H C 0.0054(3) 0.4443(8) 0.8016(3) 0.0379(15) Uani 1 1 d . . . . .
H00H H -0.025563 0.527594 0.781703 0.046 Uiso 1 1 calc R . . . .
C00I C 0.1363(3) 0.0490(8) 0.8931(3) 0.0294(12) Uani 1 1 d . . . . .
H00I H 0.107631 0.003606 0.929537 0.035 Uiso 1 1 calc R . . . .
C00J C -0.0055(3) 0.4016(9) 0.8634(4) 0.0471(18) Uani 1 1 d . . . . .
H00J H -0.043853 0.458078 0.886168 0.057 Uiso 1 1 calc R . . . .
C00K C 0.3114(4) -0.1534(8) 0.8707(4) 0.0420(16) Uani 1 1 d . . . . .
C00L C 0.3453(3) 0.0548(8) 0.5993(3) 0.0331(13) Uani 1 1 d . . . . .
H00L H 0.312445 0.017747 0.564216 0.040 Uiso 1 1 calc R . . . .
C00M C 0.3562(4) -0.2761(9) 0.6058(3) 0.0382(15) Uani 1 1 d . . . . .
H00M H 0.377425 -0.370545 0.631619 0.046 Uiso 1 1 calc R . . . .
H00N H 0.301394 -0.289863 0.606449 0.046 Uiso 1 1 calc R . . . .
C00N C 0.4559(4) -0.0342(8) 0.6275(3) 0.0341(14) Uani 1 1 d . . . . .
H00O H 0.469405 0.036959 0.664767 0.041 Uiso 1 1 calc R . . . .
C00O C 0.2523(4) 0.2914(9) 0.6093(4) 0.0450(17) Uani 1 1 d . . . . .
H00P H 0.238312 0.266363 0.567623 0.054 Uiso 1 1 calc R . . . .
C00P C 0.4572(4) 0.2772(9) 0.5768(3) 0.0351(14) Uani 1 1 d . . . . .
H00R H 0.443436 0.338419 0.615622 0.042 Uiso 1 1 calc R . . . .
H00S H 0.512119 0.276705 0.572860 0.042 Uiso 1 1 calc R . . . .
C00Q C 0.3394(4) -0.2367(10) 0.8192(5) 0.055(2) Uani 1 1 d . . . . .
H00Q H 0.318706 -0.214504 0.779301 0.066 Uiso 1 1 calc R . . . .
C00R C 0.3749(4) -0.1053(8) 0.6360(3) 0.0353(14) Uani 1 1 d . . . . .
H00T H 0.358972 -0.102308 0.680550 0.042 Uiso 1 1 calc R . . . .
C00S C 0.5582(4) -0.1643(12) 0.5585(3) 0.0483(18) Uani 1 1 d . . . . .
H00U H 0.543532 -0.088738 0.525770 0.058 Uiso 1 1 calc R . . . .
C00T C 0.3259(4) 0.2400(11) 0.6980(3) 0.0439(16) Uani 1 1 d . . . . .
H00V H 0.364019 0.175932 0.718356 0.053 Uiso 1 1 calc R . . . .
C00U C 0.2144(4) 0.4266(9) 0.6436(5) 0.062(3) Uani 1 1 d . . . . .
H00W H 0.175058 0.492241 0.625557 0.074 Uiso 1 1 calc R . . . .
C00V C 0.2383(5) 0.4565(11) 0.7045(4) 0.058(2) Uani 1 1 d . . . . .
H00X H 0.214975 0.545568 0.728222 0.069 Uiso 1 1 calc R . . . .
C00W C 0.6158(5) -0.2732(13) 0.5488(4) 0.060(2) Uani 1 1 d . . . . .
H00Y H 0.643236 -0.267865 0.511099 0.072 Uiso 1 1 calc R . . . .
C00X C 0.5387(5) -0.2758(11) 0.6602(3) 0.0522(19) Uani 1 1 d . . . . .
H00 H 0.512484 -0.277078 0.698556 0.063 Uiso 1 1 calc R . . . .
C00Y C 0.6344(5) -0.3924(11) 0.5939(6) 0.067(3) Uani 1 1 d . . . . .
H0AA H 0.673109 -0.473913 0.586235 0.080 Uiso 1 1 calc R . . . .
C00Z C 0.3419(4) -0.1833(11) 0.9271(4) 0.056(2) Uani 1 1 d . . . . .
H00Z H 0.323072 -0.123652 0.962400 0.067 Uiso 1 1 calc R . . . .
C010 C 0.3986(5) -0.3547(11) 0.8257(6) 0.075(3) Uani 1 1 d . . . . .
H010 H 0.418226 -0.414280 0.790633 0.090 Uiso 1 1 calc R . . . .
C011 C 0.2915(5) 0.3656(11) 0.7297(4) 0.057(2) Uani 1 1 d . . . . .
H011 H 0.306084 0.389268 0.771257 0.069 Uiso 1 1 calc R . . . .
C012 C 0.4284(5) -0.3829(12) 0.8857(9) 0.093(5) Uani 1 1 d . . . . .
H012 H 0.468698 -0.461549 0.891382 0.112 Uiso 1 1 calc R . . . .
C013 C 0.5987(5) -0.3949(11) 0.6482(5) 0.068(3) Uani 1 1 d . . . . .
H013 H 0.613129 -0.476160 0.679297 0.082 Uiso 1 1 calc R . . . .
C014 C 0.3998(5) -0.2984(13) 0.9341(6) 0.075(3) Uani 1 1 d . . . . .
H014 H 0.419737 -0.318254 0.974368 0.090 Uiso 1 1 calc R . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O001 C006 1.429(7) . ?
O002 C00P 1.426(7) . ?
O003 C00C 1.417(8) . ?
O004 C00M 1.407(8) . ?
C005 C007 1.388(9) . ?
C005 C008 1.387(9) . ?
C005 C00I 1.509(8) . ?
C006 C00B 1.507(8) . ?
C007 C00J 1.378(10) . ?
C008 C00G 1.407(9) . ?
C009 C00B 1.566(8) . ?
C009 C00D 1.543(8) . ?
C009 C00K 1.528(8) . ?
C00A C00N 1.525(8) . ?
C00A C00S 1.355(10) . ?
C00A C00X 1.405(11) . ?
C00B C00I 1.543(8) . ?
C00C C00D 1.520(8) . ?
C00D C00I 1.577(8) . ?
C00E C00L 1.551(9) . ?
C00E C00N 1.539(8) . ?
C00E C00P 1.556(9) . ?
C00F C00L 1.520(9) . ?
C00F C00O 1.385(10) . ?
C00F C00T 1.376(10) . ?
C00G C00H 1.357(9) . ?
C00H C00J 1.384(10) . ?
C00K C00Q 1.375(11) . ?
C00K C00Z 1.352(12) . ?
C00L C00R 1.555(9) . ?
C00M C00R 1.502(9) . ?
C00N C00R 1.565(9) . ?
C00O C00U 1.444(12) . ?
C00Q C010 1.405(13) . ?
C00S C00W 1.346(12) . ?
C00T C011 1.332(12) . ?
C00U C00V 1.400(14) . ?
C00V C011 1.301(13) . ?
C00W C00Y 1.375(15) . ?
C00X C013 1.438(13) . ?
C00Y C013 1.334(15) . ?
C00Z C014 1.372(12) . ?
C010 C012 1.414(18) . ?
C012 C014 1.331(18) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C007 C005 C00I 118.7(6) . . ?
C008 C005 C007 117.7(6) . . ?
C008 C005 C00I 123.6(5) . . ?
O001 C006 C00B 116.2(5) . . ?
C00J C007 C005 120.8(7) . . ?
C005 C008 C00G 120.7(6) . . ?
C00D C009 C00B 89.1(4) . . ?
C00K C009 C00B 119.6(5) . . ?
C00K C009 C00D 120.1(6) . . ?
C00S C00A C00N 125.7(6) . . ?
C00S C00A C00X 118.8(6) . . ?
C00X C00A C00N 115.4(7) . . ?
C006 C00B C009 116.6(5) . . ?
C006 C00B C00I 113.5(5) . . ?
C00I C00B C009 89.7(4) . . ?
O003 C00C C00D 106.8(5) . . ?
C009 C00D C00I 89.3(4) . . ?
C00C C00D C009 116.5(5) . . ?
C00C C00D C00I 119.9(5) . . ?
C00L C00E C00P 119.3(5) . . ?
C00N C00E C00L 90.1(5) . . ?
C00N C00E C00P 116.2(5) . . ?
C00O C00F C00L 116.9(6) . . ?
C00T C00F C00L 125.9(6) . . ?
C00T C00F C00O 117.2(6) . . ?
C00H C00G C008 120.6(6) . . ?
C00G C00H C00J 118.8(6) . . ?
C005 C00I C00B 116.8(5) . . ?
C005 C00I C00D 117.0(5) . . ?
C00B C00I C00D 88.8(4) . . ?
C007 C00J C00H 121.2(6) . . ?
C00Q C00K C009 116.2(7) . . ?
C00Z C00K C009 124.0(7) . . ?
C00Z C00K C00Q 119.8(7) . . ?
C00E C00L C00R 88.3(5) . . ?
C00F C00L C00E 116.8(5) . . ?
C00F C00L C00R 116.4(5) . . ?
O004 C00M C00R 117.1(6) . . ?
C00A C00N C00E 119.7(5) . . ?
C00A C00N C00R 120.8(5) . . ?
C00E C00N C00R 88.4(5) . . ?
C00F C00O C00U 119.6(7) . . ?
O002 C00P C00E 104.9(5) . . ?
C00K C00Q C010 119.7(9) . . ?
C00L C00R C00N 89.0(5) . . ?
C00M C00R C00L 113.1(6) . . ?
C00M C00R C00N 117.5(5) . . ?
C00W C00S C00A 123.1(8) . . ?
C011 C00T C00F 123.4(8) . . ?
C00V C00U C00O 116.9(7) . . ?
C011 C00V C00U 121.8(8) . . ?
C00S C00W C00Y 119.3(8) . . ?
C00A C00X C013 117.3(7) . . ?
C013 C00Y C00W 120.8(8) . . ?
C00K C00Z C014 121.0(10) . . ?
C00Q C010 C012 118.5(9) . . ?
C00V C011 C00T 121.1(9) . . ?
C014 C012 C010 119.6(8) . . ?
C00Y C013 C00X 120.5(7) . . ?
C012 C014 C00Z 121.3(11) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 0.8(6)
2 0.2(6)

