# 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_a
_database_code_depnum_ccdc_archive 'CCDC 2014881'
loop_
_audit_author_name
_audit_author_address
'Andrei Churakov'
;Institute of General and Inorganic Chemistry RAS
Russia
;
_audit_update_record             
;
2020-07-08 deposited with the CCDC.	2020-10-12 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C11 H10 O4'
_chemical_formula_sum            'C11 H10 O4'
_chemical_formula_weight         206.19

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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

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

_cell_length_a                   9.2468(4)
_cell_length_b                   15.2962(5)
_cell_length_c                   6.6028(2)
_cell_angle_alpha                90
_cell_angle_beta                 95.037(1)
_cell_angle_gamma                90
_cell_volume                     930.30(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    4087
_cell_measurement_theta_min      2.211
_cell_measurement_theta_max      30.422

_exptl_crystal_description       parallelepiped
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.472
_exptl_crystal_F_000             432
_exptl_transmission_factor_min   0.8108
_exptl_transmission_factor_max   0.8622
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.400
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    0.113
_shelx_estimated_absorpt_T_min   0.956
_shelx_estimated_absorpt_T_max   0.978
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   'SADABS (Bruker, 2016)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker SMART APEX II'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            10913
_diffrn_reflns_av_unetI/netI     0.0323
_diffrn_reflns_av_R_equivalents  0.0356
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         2.581
_diffrn_reflns_theta_max         28.997
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             2464
_reflns_number_gt                2111
_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       'APEX3 (Bruker, 2018)'
_computing_cell_refinement       'SAINT (Bruker, 2018)'
_computing_data_reduction        'SAINT (Bruker, 2018)'
_computing_structure_solution    'SHELXT (Sheldrick, 2016)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0360P)²+0.3889P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     difmap
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2464
_refine_ls_number_parameters     176
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0497
_refine_ls_R_factor_gt           0.0408
_refine_ls_wR_factor_ref         0.0932
_refine_ls_wR_factor_gt          0.0889
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_restrained_S_all      1.061
_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 0.51232(10) 0.42738(6) 0.30389(13) 0.0161(2) Uani 1 1 d . . . . .
O2 O 0.44805(9) 0.55797(5) 0.18380(13) 0.01322(19) Uani 1 1 d . . . . .
O3 O 0.66222(10) 0.71985(6) -0.00823(14) 0.0179(2) Uani 1 1 d . . . . .
O4 O 0.73271(9) 0.59986(6) 0.15889(13) 0.0150(2) Uani 1 1 d . . . . .
C1 C 0.69907(13) 0.53894(8) 0.31626(18) 0.0128(2) Uani 1 1 d . . . . .
C2 C 0.54692(12) 0.50130(8) 0.26856(17) 0.0122(2) Uani 1 1 d . . . . .
C3 C 0.48895(13) 0.65058(8) 0.19421(19) 0.0130(2) Uani 1 1 d . . . . .
C4 C 0.63271(13) 0.66189(8) 0.10334(18) 0.0134(2) Uani 1 1 d . . . . .
C5 C 0.36635(14) 0.70211(8) 0.0873(2) 0.0160(3) Uani 1 1 d . . . . .
C11 C 0.81431(13) 0.46903(8) 0.33408(19) 0.0134(2) Uani 1 1 d . . . . .
C12 C 0.88802(14) 0.44445(8) 0.1687(2) 0.0170(3) Uani 1 1 d . . . . .
C13 C 0.99466(14) 0.38003(9) 0.1918(2) 0.0206(3) Uani 1 1 d . . . . .
C14 C 1.02566(14) 0.33913(9) 0.3780(2) 0.0209(3) Uani 1 1 d . . . . .
C15 C 0.95026(14) 0.36267(9) 0.5422(2) 0.0206(3) Uani 1 1 d . . . . .
C16 C 0.84561(14) 0.42818(8) 0.52115(19) 0.0165(3) Uani 1 1 d . . . . .
H1 H 0.6971(16) 0.5701(10) 0.445(2) 0.013(3) Uiso 1 1 d . . . . .
H3 H 0.5031(16) 0.6668(10) 0.338(2) 0.014(4) Uiso 1 1 d . . . . .
H12 H 0.8667(17) 0.4739(10) 0.040(2) 0.022(4) Uiso 1 1 d . . . . .
H13 H 1.0480(19) 0.3637(11) 0.076(3) 0.030(4) Uiso 1 1 d . . . . .
H14 H 1.0994(17) 0.2947(11) 0.393(2) 0.023(4) Uiso 1 1 d . . . . .
H16 H 0.7945(18) 0.4467(11) 0.638(2) 0.023(4) Uiso 1 1 d . . . . .
H51 H 0.3486(17) 0.6858(11) -0.058(2) 0.022(4) Uiso 1 1 d . . . . .
H52 H 0.2769(17) 0.6918(10) 0.155(2) 0.021(4) Uiso 1 1 d . . . . .
H53 H 0.3900(17) 0.7636(11) 0.098(2) 0.023(4) Uiso 1 1 d . . . . .
H15 H 0.9717(18) 0.3349(11) 0.676(2) 0.025(4) Uiso 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 1.2034(15) . ?
O2 C2 1.3456(14) . ?
O2 C3 1.4663(14) . ?
O3 C4 1.1993(15) . ?
O4 C4 1.3529(14) . ?
O4 C1 1.4496(14) . ?
C1 C11 1.5069(16) . ?
C1 C2 1.5272(16) . ?
C1 H1 0.979(15) . ?
C3 C5 1.5047(17) . ?
C3 C4 1.5156(17) . ?
C3 H3 0.978(15) . ?
C5 H51 0.990(16) . ?
C5 H52 0.987(16) . ?
C5 H53 0.967(17) . ?
C11 C12 1.3891(17) . ?
C11 C16 1.3918(17) . ?
C12 C13 1.3928(18) . ?
C12 H12 0.963(16) . ?
C13 C14 1.387(2) . ?
C13 H13 0.975(17) . ?
C14 C15 1.387(2) . ?
C14 H14 0.962(16) . ?
C15 C16 1.3915(18) . ?
C15 H15 0.982(16) . ?
C16 H16 0.980(16) . ?

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 O2 C3 116.10(9) . . ?
C4 O4 C1 117.42(9) . . ?
O4 C1 C11 108.50(9) . . ?
O4 C1 C2 110.26(9) . . ?
C11 C1 C2 112.39(10) . . ?
O4 C1 H1 109.4(9) . . ?
C11 C1 H1 110.2(9) . . ?
C2 C1 H1 106.1(9) . . ?
O1 C2 O2 120.23(11) . . ?
O1 C2 C1 124.75(11) . . ?
O2 C2 C1 115.02(10) . . ?
O2 C3 C5 107.67(10) . . ?
O2 C3 C4 108.86(9) . . ?
C5 C3 C4 113.91(10) . . ?
O2 C3 H3 107.6(9) . . ?
C5 C3 H3 110.7(9) . . ?
C4 C3 H3 107.9(9) . . ?
O3 C4 O4 119.87(11) . . ?
O3 C4 C3 125.61(11) . . ?
O4 C4 C3 114.52(10) . . ?
C3 C5 H51 112.1(9) . . ?
C3 C5 H52 109.3(9) . . ?
H51 C5 H52 109.0(13) . . ?
C3 C5 H53 108.6(10) . . ?
H51 C5 H53 109.4(13) . . ?
H52 C5 H53 108.4(13) . . ?
C12 C11 C16 119.87(12) . . ?
C12 C11 C1 121.54(11) . . ?
C16 C11 C1 118.58(11) . . ?
C11 C12 C13 119.80(12) . . ?
C11 C12 H12 119.2(9) . . ?
C13 C12 H12 121.0(9) . . ?
C14 C13 C12 120.35(13) . . ?
C14 C13 H13 119.8(10) . . ?
C12 C13 H13 119.8(10) . . ?
C15 C14 C13 119.79(12) . . ?
C15 C14 H14 120.1(10) . . ?
C13 C14 H14 120.1(10) . . ?
C14 C15 C16 120.12(12) . . ?
C14 C15 H15 120.8(10) . . ?
C16 C15 H15 119.0(10) . . ?
C15 C16 C11 120.04(12) . . ?
C15 C16 H16 120.6(9) . . ?
C11 C16 H16 119.4(9) . . ?

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
C4 O4 C1 C11 172.48(10) . . . . ?
C4 O4 C1 C2 48.99(13) . . . . ?
C3 O2 C2 O1 164.86(10) . . . . ?
C3 O2 C2 C1 -14.17(14) . . . . ?
O4 C1 C2 O1 143.92(11) . . . . ?
C11 C1 C2 O1 22.72(16) . . . . ?
O4 C1 C2 O2 -37.11(13) . . . . ?
C11 C1 C2 O2 -158.30(10) . . . . ?
C2 O2 C3 C5 178.60(10) . . . . ?
C2 O2 C3 C4 54.66(13) . . . . ?
C1 O4 C4 O3 171.25(11) . . . . ?
C1 O4 C4 C3 -8.30(14) . . . . ?
O2 C3 C4 O3 137.67(12) . . . . ?
C5 C3 C4 O3 17.53(18) . . . . ?
O2 C3 C4 O4 -42.81(13) . . . . ?
C5 C3 C4 O4 -162.95(10) . . . . ?
O4 C1 C11 C12 -29.05(15) . . . . ?
C2 C1 C11 C12 93.14(13) . . . . ?
O4 C1 C11 C16 151.51(11) . . . . ?
C2 C1 C11 C16 -86.29(13) . . . . ?
C16 C11 C12 C13 -1.09(19) . . . . ?
C1 C11 C12 C13 179.49(11) . . . . ?
C11 C12 C13 C14 1.3(2) . . . . ?
C12 C13 C14 C15 -0.1(2) . . . . ?
C13 C14 C15 C16 -1.1(2) . . . . ?
C14 C15 C16 C11 1.28(19) . . . . ?
C12 C11 C16 C15 -0.17(19) . . . . ?
C1 C11 C16 C15 179.27(11) . . . . ?

_refine_diff_density_max         0.419
_refine_diff_density_min         -0.220
_refine_diff_density_rms         0.049

