# Electronic Supplementary Material (ESI) for Polymer Chemistry.
# 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. 
# 
#######################################################################

data_dtii203
_database_code_depnum_ccdc_archive 'CCDC 2089312'
loop_
_audit_author_name
_audit_author_address
'Nattamai Bhuvanesh'
;Texas A and M University
United States of America
;
_audit_update_record             
;
2021-06-10 deposited with the CCDC.	2021-09-03 downloaded from the CCDC.
;
_audit_creation_date             2019-12-12
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C9 H12 O6'
_chemical_formula_sum            'C9 H12 O6'
_chemical_formula_weight         216.19
_chemical_absolute_configuration ad
_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           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   5.9247(2)
_cell_length_b                   10.1052(4)
_cell_length_c                   16.3411(6)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     978.35(6)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9991
_cell_measurement_temperature    110.0
_cell_measurement_theta_max      70.046
_cell_measurement_theta_min      4.375
_shelx_estimated_absorpt_T_max   0.937
_shelx_estimated_absorpt_T_min   0.662
_exptl_absorpt_coefficient_mu    1.080
_exptl_absorpt_correction_T_max  0.4684
_exptl_absorpt_correction_T_min  0.3879
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1157 before and 0.0361 after correction. The Ratio of minimum to maximum transmission is 0.8281. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.468
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             456
_exptl_crystal_size_max          0.417
_exptl_crystal_size_mid          0.076
_exptl_crystal_size_min          0.061
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0175
_diffrn_reflns_av_unetI/netI     0.0066
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            24949
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         70.123
_diffrn_reflns_theta_min         5.146
_diffrn_ambient_temperature      110.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker PHOTON II'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   ?
_diffrn_special_details          ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.677
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.997
_reflns_number_gt                1843
_reflns_number_total             1860
_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 V8.38 Bruker AXS Inc., Madison, WI, USA.'
_computing_data_collection       ?
_computing_data_reduction        
'SAINT V8.38 Bruker AXS Inc., Madison, WI, USA.'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.154
_refine_diff_density_min         -0.183
_refine_diff_density_rms         0.041
_refine_ls_abs_structure_details 
;
 Flack x determined using 745 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.03(2)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.083
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     138
_refine_ls_number_reflns         1860
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0224
_refine_ls_R_factor_gt           0.0222
_refine_ls_restrained_S_all      1.083
_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)+(0.0315P)²+0.1725P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0562
_refine_ls_wR_factor_ref         0.0565
_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 C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4)
2.b Secondary CH2 refined with riding coordinates:
 C5(H5A,H5B)
2.c Idealised Me refined as rotating group:
 C8(H8A,H8B,H8C), C9(H9A,H9B,H9C)
;
_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
O1 O 0.44406(18) 0.28068(10) 0.39591(6) 0.0230(2) Uani 1 1 d . . . . .
O2 O 0.55889(18) 0.20103(12) 0.23295(7) 0.0292(3) Uani 1 1 d . . . . .
O3 O 0.84848(16) 0.31492(10) 0.29692(7) 0.0222(2) Uani 1 1 d . . . . .
O4 O 0.9061(2) 0.12497(12) 0.23492(8) 0.0334(3) Uani 1 1 d . . . . .
O5 O 0.68339(19) 0.55123(10) 0.45010(7) 0.0242(2) Uani 1 1 d . . . . .
O6 O 0.4546(2) 0.40442(11) 0.51495(7) 0.0306(3) Uani 1 1 d . . . . .
C1 C 0.4584(3) 0.37375(15) 0.32958(9) 0.0211(3) Uani 1 1 d . . . . .
H1 H 0.355982 0.450832 0.339344 0.025 Uiso 1 1 calc R . . . .
C2 C 0.7020(2) 0.41691(14) 0.33066(9) 0.0195(3) Uani 1 1 d . . . . .
H2 H 0.723932 0.504037 0.302749 0.023 Uiso 1 1 calc R . . . .
C3 C 0.7532(2) 0.42498(14) 0.42194(9) 0.0199(3) Uani 1 1 d . . . . .
H3 H 0.913731 0.403864 0.435644 0.024 Uiso 1 1 calc R . . . .
C4 C 0.5824(2) 0.32739(14) 0.46001(9) 0.0208(3) Uani 1 1 d . . . . .
H4 H 0.660577 0.252974 0.488703 0.025 Uiso 1 1 calc R . . . .
C5 C 0.3997(3) 0.30582(17) 0.25114(9) 0.0269(3) Uani 1 1 d . . . . .
H5A H 0.245875 0.268168 0.255240 0.032 Uiso 1 1 calc R . . . .
H5B H 0.400220 0.371121 0.205977 0.032 Uiso 1 1 calc R . . . .
C6 C 0.7755(3) 0.21038(15) 0.25452(9) 0.0231(3) Uani 1 1 d . . . . .
C7 C 0.5502(3) 0.53364(15) 0.52234(9) 0.0252(3) Uani 1 1 d . . . . .
C8 C 0.6969(3) 0.54024(17) 0.59819(10) 0.0336(4) Uani 1 1 d . . . . .
H8A H 0.815403 0.472804 0.594742 0.050 Uiso 1 1 calc GR . . . .
H8B H 0.604005 0.524109 0.646798 0.050 Uiso 1 1 calc GR . . . .
H8C H 0.766217 0.628070 0.602089 0.050 Uiso 1 1 calc GR . . . .
C9 C 0.3610(3) 0.63347(19) 0.52108(12) 0.0380(4) Uani 1 1 d . . . . .
H9A H 0.423171 0.722531 0.528519 0.057 Uiso 1 1 calc GR . . . .
H9B H 0.254784 0.614066 0.565462 0.057 Uiso 1 1 calc GR . . . .
H9C H 0.282132 0.628683 0.468452 0.057 Uiso 1 1 calc GR . . . .


_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 1.4376(18) . ?
O1 C4 1.4112(17) . ?
O2 C5 1.4487(19) . ?
O2 C6 1.3341(19) . ?
O3 C2 1.4556(17) . ?
O3 C6 1.3354(18) . ?
O4 C6 1.2027(19) . ?
O5 C3 1.4179(17) . ?
O5 C7 1.4312(18) . ?
O6 C4 1.4089(18) . ?
O6 C7 1.4283(18) . ?
C1 H1 1.0000 . ?
C1 C2 1.508(2) . ?
C1 C5 1.495(2) . ?
C2 H2 1.0000 . ?
C2 C3 1.524(2) . ?
C3 H3 1.0000 . ?
C3 C4 1.5441(19) . ?
C4 H4 1.0000 . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C7 C8 1.515(2) . ?
C7 C9 1.508(2) . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 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
C4 O1 C1 107.85(11) . . ?
C6 O2 C5 121.34(12) . . ?
C6 O3 C2 124.30(11) . . ?
C3 O5 C7 108.47(11) . . ?
C4 O6 C7 110.25(11) . . ?
O1 C1 H1 110.7 . . ?
O1 C1 C2 103.69(11) . . ?
O1 C1 C5 109.41(12) . . ?
C2 C1 H1 110.7 . . ?
C5 C1 H1 110.7 . . ?
C5 C1 C2 111.42(12) . . ?
O3 C2 C1 111.19(11) . . ?
O3 C2 H2 111.9 . . ?
O3 C2 C3 106.85(11) . . ?
C1 C2 H2 111.9 . . ?
C1 C2 C3 102.55(12) . . ?
C3 C2 H2 111.9 . . ?
O5 C3 C2 107.92(11) . . ?
O5 C3 H3 113.4 . . ?
O5 C3 C4 104.63(11) . . ?
C2 C3 H3 113.4 . . ?
C2 C3 C4 103.28(11) . . ?
C4 C3 H3 113.4 . . ?
O1 C4 C3 107.18(11) . . ?
O1 C4 H4 111.4 . . ?
O6 C4 O1 110.23(12) . . ?
O6 C4 C3 104.84(11) . . ?
O6 C4 H4 111.4 . . ?
C3 C4 H4 111.4 . . ?
O2 C5 C1 111.12(12) . . ?
O2 C5 H5A 109.4 . . ?
O2 C5 H5B 109.4 . . ?
C1 C5 H5A 109.4 . . ?
C1 C5 H5B 109.4 . . ?
H5A C5 H5B 108.0 . . ?
O2 C6 O3 120.31(13) . . ?
O4 C6 O2 119.85(14) . . ?
O4 C6 O3 119.84(13) . . ?
O5 C7 C8 110.66(13) . . ?
O5 C7 C9 108.40(13) . . ?
O6 C7 O5 105.21(12) . . ?
O6 C7 C8 109.67(13) . . ?
O6 C7 C9 108.42(14) . . ?
C9 C7 C8 114.09(14) . . ?
C7 C8 H8A 109.5 . . ?
C7 C8 H8B 109.5 . . ?
C7 C8 H8C 109.5 . . ?
H8A C8 H8B 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C7 C9 H9A 109.5 . . ?
C7 C9 H9B 109.5 . . ?
C7 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C1 C2 O3 75.42(13) . . . . ?
O1 C1 C2 C3 -38.47(13) . . . . ?
O1 C1 C5 O2 -62.60(16) . . . . ?
O3 C2 C3 O5 158.06(10) . . . . ?
O3 C2 C3 C4 -91.51(13) . . . . ?
O5 C3 C4 O1 108.79(12) . . . . ?
O5 C3 C4 O6 -8.36(14) . . . . ?
C1 O1 C4 O6 92.87(13) . . . . ?
C1 O1 C4 C3 -20.68(14) . . . . ?
C1 C2 C3 O5 -84.92(12) . . . . ?
C1 C2 C3 C4 25.51(13) . . . . ?
C2 O3 C6 O2 7.2(2) . . . . ?
C2 O3 C6 O4 -173.61(14) . . . . ?
C2 C1 C5 O2 51.47(16) . . . . ?
C2 C3 C4 O1 -4.06(14) . . . . ?
C2 C3 C4 O6 -121.21(12) . . . . ?
C3 O5 C7 O6 -26.72(15) . . . . ?
C3 O5 C7 C8 91.66(14) . . . . ?
C3 O5 C7 C9 -142.53(13) . . . . ?
C4 O1 C1 C2 37.49(14) . . . . ?
C4 O1 C1 C5 156.46(11) . . . . ?
C4 O6 C7 O5 21.18(16) . . . . ?
C4 O6 C7 C8 -97.86(16) . . . . ?
C4 O6 C7 C9 136.98(14) . . . . ?
C5 O2 C6 O3 3.0(2) . . . . ?
C5 O2 C6 O4 -176.18(14) . . . . ?
C5 C1 C2 O3 -42.17(16) . . . . ?
C5 C1 C2 C3 -156.05(12) . . . . ?
C6 O2 C5 C1 -32.76(19) . . . . ?
C6 O3 C2 C1 13.63(18) . . . . ?
C6 O3 C2 C3 124.79(14) . . . . ?
C7 O5 C3 C2 131.11(12) . . . . ?
C7 O5 C3 C4 21.60(14) . . . . ?
C7 O6 C4 O1 -122.96(13) . . . . ?
C7 O6 C4 C3 -7.92(16) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
