# 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_cu_zjb__ssy_5_78_1_150k_0m_a
_database_code_depnum_ccdc_archive 'CCDC 2301341'
loop_
_audit_author_name
_audit_author_address
'Siyi Shan'
;Sichuan University
China
;
_audit_update_record             
;
2023-10-15 deposited with the CCDC.	2024-01-31 downloaded from the CCDC.
;
_audit_creation_date             2023-10-10
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C9 H14 O3'
_chemical_formula_sum            'C9 H14 O3'
_chemical_formula_weight         170.20
_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+1/2, -z'
'-x, y+1/2, -z+1/2'
'-x+1/2, -y, z+1/2'

_cell_length_a                   5.3341(11)
_cell_length_b                   7.7048(16)
_cell_length_c                   20.413(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     838.9(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9671
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      68.487
_cell_measurement_theta_min      4.332
_shelx_estimated_absorpt_T_max   0.833
_shelx_estimated_absorpt_T_min   0.683
_exptl_absorpt_coefficient_mu    0.825
_exptl_absorpt_correction_T_max  0.7531
_exptl_absorpt_correction_T_min  0.4586
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1507 before and 0.0940 after correction.
The Ratio of minimum to maximum transmission is 0.6089.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.348
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             368
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.45
_exptl_crystal_size_min          0.23
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0712
_diffrn_reflns_av_unetI/netI     0.0318
_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       -6
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            17245
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.606
_diffrn_reflns_theta_min         4.332
_diffrn_ambient_temperature      150.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   ?
_diffrn_source_current           1.1
_diffrn_source_power             0.055
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.642
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.990
_reflns_number_gt                1543
_reflns_number_total             1555
_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 V8.40B (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2014/7 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.136
_refine_diff_density_min         -0.191
_refine_diff_density_rms         0.051
_refine_ls_abs_structure_details 
;
 Flack x determined using 600 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.16(7)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.096
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     109
_refine_ls_number_reflns         1555
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0312
_refine_ls_R_factor_gt           0.0310
_refine_ls_restrained_S_all      1.096
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0402P)²+0.1664P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0774
_refine_ls_wR_factor_ref         0.0775
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Ternary CH refined with riding coordinates:
 C3(H3), C7(H7)
2.b Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B), C2(H2A,H2B), C4(H4A,H4B), C6(H6A,H6B), C8(H8A,H8B), C9(H9A,H9B)
;
_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 0.4694(2) 0.18691(16) 0.58027(5) 0.0234(3) Uani 1 1 d . . . . .
O2 O 0.7040(2) 0.01790(17) 0.64244(6) 0.0297(3) Uani 1 1 d . . . . .
O3 O 0.4140(3) 0.17766(15) 0.69142(6) 0.0247(3) Uani 1 1 d . . . . .
C1 C 0.1973(4) 0.7255(2) 0.58042(9) 0.0309(4) Uani 1 1 d . . . . .
H1A H 0.0249 0.7484 0.5647 0.037 Uiso 1 1 calc R U . . .
H1B H 0.3095 0.8141 0.5611 0.037 Uiso 1 1 calc R U . . .
C2 C 0.2798(4) 0.5457(2) 0.55803(9) 0.0258(4) Uani 1 1 d . . . . .
H2A H 0.4586 0.5285 0.5694 0.031 Uiso 1 1 calc R U . . .
H2B H 0.2638 0.5377 0.5098 0.031 Uiso 1 1 calc R U . . .
C3 C 0.1230(3) 0.4019(2) 0.58986(8) 0.0203(4) Uani 1 1 d . . . . .
H3 H -0.0528 0.4181 0.5740 0.024 Uiso 1 1 calc R U . . .
C4 C 0.2031(4) 0.2227(2) 0.56817(8) 0.0226(4) Uani 1 1 d . . . . .
H4A H 0.1009 0.1353 0.5916 0.027 Uiso 1 1 calc R U . . .
H4B H 0.1690 0.2102 0.5207 0.027 Uiso 1 1 calc R U . . .
C5 C 0.5384(3) 0.1218(2) 0.63830(8) 0.0200(4) Uani 1 1 d . . . . .
C6 C 0.3588(3) 0.3635(2) 0.69697(8) 0.0226(4) Uani 1 1 d . . . . .
H6A H 0.4972 0.4300 0.6766 0.027 Uiso 1 1 calc R U . . .
H6B H 0.3522 0.3952 0.7439 0.027 Uiso 1 1 calc R U . . .
C7 C 0.1137(3) 0.4158(2) 0.66477(8) 0.0198(4) Uani 1 1 d . . . . .
H7 H -0.0196 0.3350 0.6808 0.024 Uiso 1 1 calc R U . . .
C8 C 0.2040(4) 0.7398(2) 0.65510(9) 0.0268(4) Uani 1 1 d . . . . .
H8A H 0.3789 0.7271 0.6706 0.032 Uiso 1 1 calc R U . . .
H8B H 0.1430 0.8558 0.6686 0.032 Uiso 1 1 calc R U . . .
C9 C 0.0415(3) 0.6005(2) 0.68626(9) 0.0247(4) Uani 1 1 d . . . . .
H9A H -0.1359 0.6220 0.6745 0.030 Uiso 1 1 calc R U . . .
H9B H 0.0560 0.6089 0.7345 0.030 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C4 1.468(2) . ?
O1 C5 1.338(2) . ?
O2 C5 1.195(2) . ?
O3 C5 1.342(2) . ?
O3 C6 1.466(2) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C1 C2 1.524(2) . ?
C1 C8 1.529(3) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C2 C3 1.533(3) . ?
C3 H3 1.0000 . ?
C3 C4 1.511(2) . ?
C3 C7 1.534(2) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C6 C7 1.518(2) . ?
C7 H7 1.0000 . ?
C7 C9 1.538(2) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C8 C9 1.519(3) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?

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
C5 O1 C4 119.05(13) . . ?
C5 O3 C6 118.37(13) . . ?
H1A C1 H1B 108.0 . . ?
C2 C1 H1A 109.4 . . ?
C2 C1 H1B 109.4 . . ?
C2 C1 C8 110.97(15) . . ?
C8 C1 H1A 109.4 . . ?
C8 C1 H1B 109.4 . . ?
C1 C2 H2A 109.2 . . ?
C1 C2 H2B 109.2 . . ?
C1 C2 C3 111.85(16) . . ?
H2A C2 H2B 107.9 . . ?
C3 C2 H2A 109.2 . . ?
C3 C2 H2B 109.2 . . ?
C2 C3 H3 106.5 . . ?
C2 C3 C7 112.94(14) . . ?
C4 C3 C2 112.43(15) . . ?
C4 C3 H3 106.5 . . ?
C4 C3 C7 111.42(13) . . ?
C7 C3 H3 106.5 . . ?
O1 C4 C3 113.34(14) . . ?
O1 C4 H4A 108.9 . . ?
O1 C4 H4B 108.9 . . ?
C3 C4 H4A 108.9 . . ?
C3 C4 H4B 108.9 . . ?
H4A C4 H4B 107.7 . . ?
O1 C5 O3 117.31(14) . . ?
O2 C5 O1 121.13(15) . . ?
O2 C5 O3 121.56(15) . . ?
O3 C6 H6A 108.9 . . ?
O3 C6 H6B 108.9 . . ?
O3 C6 C7 113.53(14) . . ?
H6A C6 H6B 107.7 . . ?
C7 C6 H6A 108.9 . . ?
C7 C6 H6B 108.9 . . ?
C3 C7 H7 107.8 . . ?
C3 C7 C9 110.94(14) . . ?
C6 C7 C3 112.65(14) . . ?
C6 C7 H7 107.8 . . ?
C6 C7 C9 109.76(14) . . ?
C9 C7 H7 107.8 . . ?
C1 C8 H8A 109.5 . . ?
C1 C8 H8B 109.5 . . ?
H8A C8 H8B 108.1 . . ?
C9 C8 C1 110.68(15) . . ?
C9 C8 H8A 109.5 . . ?
C9 C8 H8B 109.5 . . ?
C7 C9 H9A 109.0 . . ?
C7 C9 H9B 109.0 . . ?
C8 C9 C7 113.03(14) . . ?
C8 C9 H9A 109.0 . . ?
C8 C9 H9B 109.0 . . ?
H9A C9 H9B 107.8 . . ?

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
O3 C6 C7 C3 -68.82(18) . . . . ?
O3 C6 C7 C9 167.03(14) . . . . ?
C1 C2 C3 C4 -179.91(15) . . . . ?
C1 C2 C3 C7 -52.8(2) . . . . ?
C1 C8 C9 C7 55.8(2) . . . . ?
C2 C1 C8 C9 -56.8(2) . . . . ?
C2 C3 C4 O1 56.22(18) . . . . ?
C2 C3 C7 C6 -73.28(19) . . . . ?
C2 C3 C7 C9 50.2(2) . . . . ?
C3 C7 C9 C8 -52.2(2) . . . . ?
C4 O1 C5 O2 143.58(16) . . . . ?
C4 O1 C5 O3 -36.3(2) . . . . ?
C4 C3 C7 C6 54.39(19) . . . . ?
C4 C3 C7 C9 177.90(15) . . . . ?
C5 O1 C4 C3 87.76(18) . . . . ?
C5 O3 C6 C7 87.99(18) . . . . ?
C6 O3 C5 O1 -43.1(2) . . . . ?
C6 O3 C5 O2 137.00(17) . . . . ?
C6 C7 C9 C8 72.90(18) . . . . ?
C7 C3 C4 O1 -71.73(18) . . . . ?
C8 C1 C2 C3 55.5(2) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
