# Supplementary Information (SI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 2026

####################################################################### 
# 
# 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_(endo-1)(exo-1)-240K
_database_code_depnum_ccdc_archive 'CCDC 2376886'
loop_
_audit_author_name
_audit_author_address
'Cameron Lennox'
;McGill University
Canada
;
_audit_update_record             
;
2024-11-06 deposited with the CCDC.	2026-05-12 downloaded from the CCDC.
;
_audit_creation_date             2024-06-11
_audit_creation_method           
;
Olex2 1.5
(compiled 2024.01.12 svn.r2f8d729c for OlexSys, GUI svn.r6928)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        
'7-oxabicyclo(2.2.1)-5-heptene-2,3-dicarboxylic anhydride cocrystal'
_chemical_formula_moiety         '2(C8 H6 O4)'
_chemical_formula_sum            'C16 H12 O8'
_chemical_formula_weight         332.26
_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      monoclinic
_space_group_IT_number           7
_space_group_name_H-M_alt        'P 1 n 1'
_space_group_name_Hall           'P -2yac'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'x+1/2, -y, z+1/2'

_cell_length_a                   11.9288(4)
_cell_length_b                   5.3945(2)
_cell_length_c                   11.9826(5)
_cell_angle_alpha                90
_cell_angle_beta                 110.504(3)
_cell_angle_gamma                90
_cell_volume                     722.23(5)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    2703
_cell_measurement_temperature    240
_cell_measurement_theta_max      144.6
_cell_measurement_theta_min      8.98
_shelx_estimated_absorpt_T_max   0.673
_shelx_estimated_absorpt_T_min   0.565
_exptl_absorpt_coefficient_mu    1.074
_exptl_absorpt_correction_T_max  0.7536
_exptl_absorpt_correction_T_min  0.5041
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS-2012/1, G. Sheldrick'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colorless
_exptl_crystal_colour_lustre     clear
_exptl_crystal_density_diffrn    1.528
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       rhombic
_exptl_crystal_F_000             344
_exptl_crystal_size_max          0.6
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.4
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0972
_diffrn_reflns_av_unetI/netI     0.1055
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            6464
_diffrn_reflns_point_group_measured_fraction_full 0.957
_diffrn_reflns_point_group_measured_fraction_max 0.944
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         72.277
_diffrn_reflns_theta_min         4.501
_diffrn_ambient_temperature      240.00
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker PHOTON 100 CMOS'
_diffrn_measurement_method       'omega and f scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   ?
_reflns_Friedel_coverage         0.889
_reflns_Friedel_fraction_full    0.917
_reflns_Friedel_fraction_max     0.890
_reflns_number_gt                1684
_reflns_number_total             2703
_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 V8.35A, Bruker-AXS'
_computing_data_collection       'APEX 2, Bruker-AXS'
_computing_data_reduction        'SAINT V8.35A, Bruker-AXS'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'olex2.solve 1.5 (Bourhis et al., 2015)'
_refine_diff_density_max         0.193
_refine_diff_density_min         -0.183
_refine_diff_density_rms         0.049
_refine_ls_abs_structure_details 
;
 Flack x determined using 526 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.1(4)
_refine_ls_extinction_coef       0.021(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     218
_refine_ls_number_reflns         2703
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.1039
_refine_ls_R_factor_gt           0.0566
_refine_ls_restrained_S_all      1.055
_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)+(0.0568P)²+0.0760P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1374
_refine_ls_wR_factor_ref         0.1771
_refine_special_details          ?
_olex2_refinement_description    
;
1.a Ternary CH refined with riding coordinates:
 C13(H13), C14(H14), C11(H11), C4(H4), C5(H5), C6(H6), C12(H12), C3(H3)
1.b Aromatic/amide H refined with riding coordinates:
 C15(H15), C7(H7), C16(H16), C8(H8)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_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
O5 O 0.6592(5) 0.5436(10) 0.4992(5) 0.0603(13) Uani 1 1 d . . . . .
O6 O 0.6174(5) 0.4867(12) 0.3045(5) 0.0750(16) Uani 1 1 d . . . . .
O3 O 0.0716(5) 0.1325(13) 0.3400(5) 0.0804(19) Uani 1 1 d . . . . .
O8 O 0.9127(4) 0.3109(10) 0.5315(5) 0.0587(13) Uani 1 1 d . . . . .
O1 O 0.2680(5) 0.0860(10) 0.3823(5) 0.0623(13) Uani 1 1 d . . . . .
O4 O 0.2962(6) 0.6530(10) 0.6258(5) 0.0737(16) Uani 1 1 d . . . . .
O7 O 0.7175(6) 0.5087(14) 0.6959(6) 0.087(2) Uani 1 1 d . . . . .
O2 O 0.4647(5) 0.1313(12) 0.4376(7) 0.089(2) Uani 1 1 d . . . . .
C9 C 0.6596(6) 0.4030(14) 0.4025(7) 0.0538(17) Uani 1 1 d . . . . .
C2 C 0.1700(6) 0.2197(16) 0.3836(7) 0.0596(19) Uani 1 1 d . . . . .
C15 C 0.8993(6) -0.0971(15) 0.4754(8) 0.061(2) Uani 1 1 d . . . . .
H15 H 0.909769 -0.227976 0.428156 0.073 Uiso 1 1 calc R U . . .
C13 C 0.8478(6) 0.1526(14) 0.4336(6) 0.0536(17) Uani 1 1 d . . . . .
H13 H 0.850090 0.203617 0.355025 0.064 Uiso 1 1 calc R U . . .
C10 C 0.7105(6) 0.4153(16) 0.6030(7) 0.0600(19) Uani 1 1 d . . . . .
C14 C 0.8939(7) 0.1605(15) 0.6234(7) 0.0587(19) Uani 1 1 d . . . . .
H14 H 0.935817 0.216134 0.706327 0.070 Uiso 1 1 calc R U . . .
C7 C 0.3618(9) 0.2529(19) 0.6609(8) 0.080(3) Uani 1 1 d . . . . .
H7 H 0.416740 0.129011 0.700390 0.095 Uiso 1 1 calc R U . . .
C1 C 0.3710(6) 0.2206(16) 0.4313(7) 0.0598(19) Uani 1 1 d . . . . .
C11 C 0.7211(5) 0.1568(13) 0.4445(6) 0.0497(17) Uani 1 1 d . . . . .
H11 H 0.671184 0.012426 0.406293 0.060 Uiso 1 1 calc R U . . .
C16 C 0.9274(7) -0.0969(16) 0.5927(7) 0.062(2) Uani 1 1 d . . . . .
H16 H 0.960900 -0.227734 0.645725 0.074 Uiso 1 1 calc R U . . .
C4 C 0.2086(6) 0.4572(15) 0.4456(6) 0.0558(18) Uani 1 1 d . . . . .
H4 H 0.168520 0.599024 0.394800 0.067 Uiso 1 1 calc R U . . .
C5 C 0.3893(7) 0.4915(17) 0.6146(7) 0.067(2) Uani 1 1 d . . . . .
H5 H 0.472319 0.552290 0.652635 0.080 Uiso 1 1 calc R U . . .
C6 C 0.1997(6) 0.4763(16) 0.5728(6) 0.061(2) Uani 1 1 d . . . . .
H6 H 0.120382 0.526447 0.574356 0.073 Uiso 1 1 calc R U . . .
C12 C 0.7537(6) 0.1624(14) 0.5800(6) 0.0529(17) Uani 1 1 d . . . . .
H12 H 0.719487 0.023116 0.611436 0.063 Uiso 1 1 calc R U . . .
C3 C 0.3446(6) 0.4649(15) 0.4750(7) 0.0577(18) Uani 1 1 d . . . . .
H3 H 0.369587 0.606127 0.436435 0.069 Uiso 1 1 calc R U . . .
C8 C 0.2480(9) 0.2490(17) 0.6364(7) 0.071(2) Uani 1 1 d . . . . .
H8 H 0.204035 0.122342 0.656061 0.085 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
O5 C9 1.386(9) . ?
O5 C10 1.366(9) . ?
O6 C9 1.193(9) . ?
O3 C2 1.200(9) . ?
O8 C13 1.438(9) . ?
O8 C14 1.447(9) . ?
O1 C2 1.378(9) . ?
O1 C1 1.370(9) . ?
O4 C5 1.455(10) . ?
O4 C6 1.458(10) . ?
O7 C10 1.198(9) . ?
O2 C1 1.195(9) . ?
C9 C11 1.515(10) . ?
C2 C4 1.472(12) . ?
C15 H15 0.9400 . ?
C15 C13 1.493(11) . ?
C15 C16 1.326(11) . ?
C13 H13 0.9900 . ?
C13 C11 1.562(9) . ?
C10 C12 1.517(11) . ?
C14 H14 0.9900 . ?
C14 C16 1.525(11) . ?
C14 C12 1.568(10) . ?
C7 H7 0.9400 . ?
C7 C5 1.483(14) . ?
C7 C8 1.285(13) . ?
C1 C3 1.492(12) . ?
C11 H11 0.9900 . ?
C11 C12 1.533(9) . ?
C16 H16 0.9400 . ?
C4 H4 0.9900 . ?
C4 C6 1.568(10) . ?
C4 C3 1.535(10) . ?
C5 H5 0.9900 . ?
C5 C3 1.574(11) . ?
C6 H6 0.9900 . ?
C6 C8 1.452(12) . ?
C12 H12 0.9900 . ?
C3 H3 0.9900 . ?
C8 H8 0.9400 . ?

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
C10 O5 C9 110.6(6) . . ?
C13 O8 C14 96.1(5) . . ?
C1 O1 C2 110.8(6) . . ?
C5 O4 C6 94.6(6) . . ?
O5 C9 C11 110.2(6) . . ?
O6 C9 O5 119.5(7) . . ?
O6 C9 C11 130.3(7) . . ?
O3 C2 O1 119.6(8) . . ?
O3 C2 C4 130.3(7) . . ?
O1 C2 C4 110.1(6) . . ?
C13 C15 H15 127.0 . . ?
C16 C15 H15 127.0 . . ?
C16 C15 C13 106.1(7) . . ?
O8 C13 C15 102.8(6) . . ?
O8 C13 H13 115.1 . . ?
O8 C13 C11 100.5(5) . . ?
C15 C13 H13 115.1 . . ?
C15 C13 C11 106.4(6) . . ?
C11 C13 H13 115.1 . . ?
O5 C10 C12 111.3(6) . . ?
O7 C10 O5 119.7(8) . . ?
O7 C10 C12 129.0(7) . . ?
O8 C14 H14 115.8 . . ?
O8 C14 C16 101.7(6) . . ?
O8 C14 C12 100.1(5) . . ?
C16 C14 H14 115.8 . . ?
C16 C14 C12 105.4(6) . . ?
C12 C14 H14 115.8 . . ?
C5 C7 H7 126.8 . . ?
C8 C7 H7 126.8 . . ?
C8 C7 C5 106.5(8) . . ?
O1 C1 C3 110.5(6) . . ?
O2 C1 O1 119.5(8) . . ?
O2 C1 C3 130.0(7) . . ?
C9 C11 C13 110.8(6) . . ?
C9 C11 H11 113.2 . . ?
C9 C11 C12 104.4(6) . . ?
C13 C11 H11 113.2 . . ?
C12 C11 C13 101.3(5) . . ?
C12 C11 H11 113.2 . . ?
C15 C16 C14 105.4(7) . . ?
C15 C16 H16 127.3 . . ?
C14 C16 H16 127.3 . . ?
C2 C4 H4 111.4 . . ?
C2 C4 C6 115.6(7) . . ?
C2 C4 C3 105.0(6) . . ?
C6 C4 H4 111.4 . . ?
C3 C4 H4 111.4 . . ?
C3 C4 C6 101.6(5) . . ?
O4 C5 C7 102.1(7) . . ?
O4 C5 H5 115.6 . . ?
O4 C5 C3 99.6(6) . . ?
C7 C5 H5 115.6 . . ?
C7 C5 C3 106.4(7) . . ?
C3 C5 H5 115.6 . . ?
O4 C6 C4 98.9(6) . . ?
O4 C6 H6 115.3 . . ?
C4 C6 H6 115.3 . . ?
C8 C6 O4 102.5(6) . . ?
C8 C6 C4 107.8(7) . . ?
C8 C6 H6 115.3 . . ?
C10 C12 C14 109.7(6) . . ?
C10 C12 C11 103.5(6) . . ?
C10 C12 H12 113.7 . . ?
C14 C12 H12 113.7 . . ?
C11 C12 C14 101.3(5) . . ?
C11 C12 H12 113.7 . . ?
C1 C3 C4 103.4(6) . . ?
C1 C3 C5 114.8(7) . . ?
C1 C3 H3 112.4 . . ?
C4 C3 C5 100.6(6) . . ?
C4 C3 H3 112.4 . . ?
C5 C3 H3 112.4 . . ?
C7 C8 C6 107.4(9) . . ?
C7 C8 H8 126.3 . . ?
C6 C8 H8 126.3 . . ?

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
O5 C9 C11 C13 -106.0(6) . . . . ?
O5 C9 C11 C12 2.2(7) . . . . ?
O5 C10 C12 C14 107.8(7) . . . . ?
O5 C10 C12 C11 0.4(8) . . . . ?
O6 C9 C11 C13 72.1(10) . . . . ?
O6 C9 C11 C12 -179.7(8) . . . . ?
O3 C2 C4 C6 71.5(11) . . . . ?
O3 C2 C4 C3 -177.5(8) . . . . ?
O8 C13 C11 C9 73.9(6) . . . . ?
O8 C13 C11 C12 -36.3(7) . . . . ?
O8 C14 C16 C15 -30.7(7) . . . . ?
O8 C14 C12 C10 -72.9(7) . . . . ?
O8 C14 C12 C11 36.0(7) . . . . ?
O1 C2 C4 C6 -106.7(7) . . . . ?
O1 C2 C4 C3 4.3(8) . . . . ?
O1 C1 C3 C4 0.4(8) . . . . ?
O1 C1 C3 C5 109.0(7) . . . . ?
O4 C5 C3 C1 -147.3(6) . . . . ?
O4 C5 C3 C4 -37.1(8) . . . . ?
O4 C6 C8 C7 -32.6(9) . . . . ?
O7 C10 C12 C14 -71.2(11) . . . . ?
O7 C10 C12 C11 -178.6(9) . . . . ?
O2 C1 C3 C4 -176.6(9) . . . . ?
O2 C1 C3 C5 -68.0(12) . . . . ?
C9 O5 C10 O7 -179.9(8) . . . . ?
C9 O5 C10 C12 1.1(8) . . . . ?
C9 C11 C12 C10 -1.5(7) . . . . ?
C9 C11 C12 C14 -115.1(6) . . . . ?
C2 O1 C1 O2 179.7(8) . . . . ?
C2 O1 C1 C3 2.4(8) . . . . ?
C2 C4 C6 O4 151.4(6) . . . . ?
C2 C4 C6 C8 45.2(9) . . . . ?
C2 C4 C3 C1 -2.8(8) . . . . ?
C2 C4 C3 C5 -121.6(7) . . . . ?
C15 C13 C11 C9 -179.3(6) . . . . ?
C15 C13 C11 C12 70.5(7) . . . . ?
C13 O8 C14 C16 48.4(6) . . . . ?
C13 O8 C14 C12 -59.9(6) . . . . ?
C13 C15 C16 C14 -0.8(7) . . . . ?
C13 C11 C12 C10 113.7(6) . . . . ?
C13 C11 C12 C14 0.0(7) . . . . ?
C10 O5 C9 O6 179.6(7) . . . . ?
C10 O5 C9 C11 -2.1(8) . . . . ?
C14 O8 C13 C15 -49.5(6) . . . . ?
C14 O8 C13 C11 60.1(6) . . . . ?
C7 C5 C3 C1 -41.7(8) . . . . ?
C7 C5 C3 C4 68.6(8) . . . . ?
C1 O1 C2 O3 177.3(7) . . . . ?
C1 O1 C2 C4 -4.3(8) . . . . ?
C16 C15 C13 O8 32.5(7) . . . . ?
C16 C15 C13 C11 -72.7(7) . . . . ?
C16 C14 C12 C10 -178.2(6) . . . . ?
C16 C14 C12 C11 -69.2(7) . . . . ?
C4 C6 C8 C7 71.1(9) . . . . ?
C5 O4 C6 C4 -62.5(7) . . . . ?
C5 O4 C6 C8 48.1(7) . . . . ?
C5 C7 C8 C6 1.3(10) . . . . ?
C6 O4 C5 C7 -46.9(7) . . . . ?
C6 O4 C5 C3 62.2(7) . . . . ?
C6 C4 C3 C1 118.0(7) . . . . ?
C6 C4 C3 C5 -0.9(8) . . . . ?
C12 C14 C16 C15 73.4(7) . . . . ?
C3 C4 C6 O4 38.4(7) . . . . ?
C3 C4 C6 C8 -67.8(8) . . . . ?
C8 C7 C5 O4 30.5(9) . . . . ?
C8 C7 C5 C3 -73.5(8) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_(endo-1)-250K
_database_code_depnum_ccdc_archive 'CCDC 2376890'
loop_
_audit_author_name
_audit_author_address
'Cameron Lennox'
;McGill University
Canada
;
_audit_update_record             
;
2024-11-06 deposited with the CCDC.	2026-05-12 downloaded from the CCDC.
;
_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        
'endo-7-oxabicyclo(2.2.1)-5-heptene-2,3-dicarboxylic anhydride'
_chemical_name_common            ?
_chemical_formula_moiety         'C8 H6 O4'
_chemical_formula_sum            'C8 H6 O4'
_chemical_properties_physical    moisture-sensitive
_exptl_crystal_recrystallization_method neat
_chemical_melting_point          ?
_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_diffrn_ambient_temperature      250
_diffrn_ambient_pressure         1013
_chemical_formula_weight         166.13
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'

_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'
_chemical_absolute_configuration .
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'

_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.
;
_cell_length_a                   11.2483(3)
_cell_length_b                   5.68780(10)
_cell_length_c                   11.3895(3)
_cell_angle_alpha                90
_cell_angle_beta                 103.8840(10)
_cell_angle_gamma                90
_cell_volume                     707.39(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    250(2)
_cell_measurement_reflns_used    14306
_cell_measurement_theta_min      22.405
_cell_measurement_theta_max      144.322
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.560
_exptl_crystal_F_000             344
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.447
_exptl_crystal_size_mid          0.254
_exptl_crystal_size_min          0.182
_exptl_absorpt_coefficient_mu    1.097
_shelx_estimated_absorpt_T_min   0.640
_shelx_estimated_absorpt_T_max   0.825
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5756
_exptl_absorpt_correction_T_max  0.7536
_exptl_absorpt_process_details   'SADABS-2012/1, G. Sheldrick'
_exptl_absorpt_special_details   ?
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   'sealed x-ray tube'
_diffrn_source_type              'Bruker D8 Venture'
_diffrn_measurement_device_type  'Bruker PHOTON 100 CMOS'
_diffrn_measurement_method       'omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            12818
_diffrn_reflns_av_unetI/netI     0.0226
_diffrn_reflns_av_R_equivalents  0.0424
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         11.213
_diffrn_reflns_theta_max         72.308
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.968
_diffrn_measured_fraction_theta_full 0.966
_diffrn_reflns_Laue_measured_fraction_max 0.968
_diffrn_reflns_Laue_measured_fraction_full 0.966
_diffrn_reflns_point_group_measured_fraction_max 0.968
_diffrn_reflns_point_group_measured_fraction_full 0.966
_reflns_number_total             1344
_reflns_number_gt                1251
_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       'APEX 2, Bruker-AXS'
_computing_cell_refinement       'SAINT V8.35A, Bruker-AXS'
_computing_data_reduction        'SAINT V8.35A, Bruker-AXS'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_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)+(0.0343P)²+0.2662P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         1344
_refine_ls_number_parameters     109
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0404
_refine_ls_R_factor_gt           0.0380
_refine_ls_wR_factor_ref         0.0949
_refine_ls_wR_factor_gt          0.0928
_refine_ls_goodness_of_fit_ref   1.090
_refine_ls_restrained_S_all      1.090
_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 0.29392(9) -0.06840(18) 0.09929(8) 0.0394(3) Uani 1 1 d . . . . .
C1 C 0.17169(12) -0.0526(2) 0.10298(11) 0.0339(3) Uani 1 1 d . . . . .
O2 O 0.10446(10) -0.21383(19) 0.07045(9) 0.0460(3) Uani 1 1 d . . . . .
C2 C 0.35637(13) 0.1361(3) 0.14302(12) 0.0378(3) Uani 1 1 d . . . . .
C3 C 0.14828(12) 0.1797(2) 0.15501(12) 0.0336(3) Uani 1 1 d . . . . .
H3 H 0.085980 0.271509 0.098586 0.040 Uiso 1 1 calc R U . . .
O3 O 0.46123(10) 0.1579(2) 0.14261(12) 0.0578(4) Uani 1 1 d . . . . .
C4 C 0.27210(12) 0.3023(2) 0.18535(12) 0.0351(3) Uani 1 1 d . . . . .
H4 H 0.268658 0.455734 0.145516 0.042 Uiso 1 1 calc R U . . .
O4 O 0.17278(9) 0.37718(18) 0.33552(10) 0.0433(3) Uani 1 1 d . . . . .
C5 C 0.12039(12) 0.1605(2) 0.28364(13) 0.0378(3) Uani 1 1 d . . . . .
H5 H 0.034051 0.137008 0.283549 0.045 Uiso 1 1 calc R U . . .
C7 C 0.20714(15) -0.0185(3) 0.35324(12) 0.0430(4) Uani 1 1 d . . . . .
H7 H 0.188419 -0.169821 0.374000 0.052 Uiso 1 1 calc R U . . .
C6 C 0.29554(13) 0.3275(3) 0.32633(14) 0.0414(4) Uani 1 1 d . . . . .
H6 H 0.357329 0.444087 0.363392 0.050 Uiso 1 1 calc R U . . .
C8 C 0.31547(15) 0.0834(3) 0.37886(12) 0.0473(4) Uani 1 1 d . . . . .
H8 H 0.389242 0.018057 0.420831 0.057 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 C2 1.3881(18) . ?
O1 C1 1.3885(16) . ?
C1 O2 1.1898(17) . ?
C1 C3 1.4972(18) . ?
C2 O3 1.1871(18) . ?
C2 C4 1.4981(19) . ?
C3 C4 1.5212(18) . ?
C3 C5 1.5739(19) . ?
C3 H3 0.9800 . ?
C4 C6 1.5700(19) . ?
C4 H4 0.9800 . ?
O4 C5 1.4313(16) . ?
O4 C6 1.4377(17) . ?
C5 C7 1.499(2) . ?
C5 H5 0.9800 . ?
C7 C8 1.317(2) . ?
C7 H7 0.9300 . ?
C6 C8 1.507(2) . ?
C6 H6 0.9800 . ?
C8 H8 0.9300 . ?

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 110.76(10) . . ?
O2 C1 O1 120.04(12) . . ?
O2 C1 C3 130.14(12) . . ?
O1 C1 C3 109.79(11) . . ?
O3 C2 O1 120.26(13) . . ?
O3 C2 C4 129.89(14) . . ?
O1 C2 C4 109.84(11) . . ?
C1 C3 C4 104.84(10) . . ?
C1 C3 C5 113.59(11) . . ?
C4 C3 C5 101.34(10) . . ?
C1 C3 H3 112.1 . . ?
C4 C3 H3 112.1 . . ?
C5 C3 H3 112.1 . . ?
C2 C4 C3 104.67(11) . . ?
C2 C4 C6 115.01(11) . . ?
C3 C4 C6 101.19(10) . . ?
C2 C4 H4 111.8 . . ?
C3 C4 H4 111.8 . . ?
C6 C4 H4 111.8 . . ?
C5 O4 C6 96.20(10) . . ?
O4 C5 C7 102.43(11) . . ?
O4 C5 C3 99.79(10) . . ?
C7 C5 C3 106.84(10) . . ?
O4 C5 H5 115.3 . . ?
C7 C5 H5 115.3 . . ?
C3 C5 H5 115.3 . . ?
C8 C7 C5 105.58(13) . . ?
C8 C7 H7 127.2 . . ?
C5 C7 H7 127.2 . . ?
O4 C6 C8 101.90(12) . . ?
O4 C6 C4 99.43(11) . . ?
C8 C6 C4 107.13(11) . . ?
O4 C6 H6 115.5 . . ?
C8 C6 H6 115.5 . . ?
C4 C6 H6 115.5 . . ?
C7 C8 C6 106.01(13) . . ?
C7 C8 H8 127.0 . . ?
C6 C8 H8 127.0 . . ?

_refine_diff_density_max         0.201
_refine_diff_density_min         -0.139
_refine_diff_density_rms         0.032
####################################################################### 
# 
# 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_(endo-1)-150K
_database_code_depnum_ccdc_archive 'CCDC 2376892'
loop_
_audit_author_name
_audit_author_address
'Cameron Lennox'
;McGill University
Canada
;
_audit_update_record             
;
2024-11-06 deposited with the CCDC.	2026-05-12 downloaded from the CCDC.
;
_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        
'endo-7-oxabicyclo(2.2.1)-5-heptene-2,3-dicarboxylic anhydride'
_chemical_name_common            ?
_chemical_formula_moiety         'C8 H6 O4'
_chemical_formula_sum            'C8 H6 O4'
_chemical_properties_physical    moisture-sensitive
_exptl_crystal_recrystallization_method neat
_chemical_melting_point          ?
_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_diffrn_ambient_temperature      150(2)
_diffrn_ambient_pressure         1013
_chemical_formula_weight         166.13
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'

_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'
_chemical_absolute_configuration .
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'

_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.
;
_cell_length_a                   11.1987(6)
_cell_length_b                   5.6558(3)
_cell_length_c                   11.3247(6)
_cell_angle_alpha                90
_cell_angle_beta                 103.949(2)
_cell_angle_gamma                90
_cell_volume                     696.13(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    6881
_cell_measurement_theta_min      54.370
_cell_measurement_theta_max      144.121
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.585
_exptl_crystal_F_000             344
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.447
_exptl_crystal_size_mid          0.254
_exptl_crystal_size_min          0.182
_exptl_absorpt_coefficient_mu    1.114
_shelx_estimated_absorpt_T_min   0.636
_shelx_estimated_absorpt_T_max   0.823
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.4196
_exptl_absorpt_correction_T_max  0.7535
_exptl_absorpt_process_details   'SADABS-2012/1, G. Sheldrick'
_exptl_absorpt_special_details   ?
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   'sealed x-ray tube'
_diffrn_source_type              'Bruker D8 Advance'
_diffrn_measurement_device_type  'Bruker PHOTON 100 CMOS'
_diffrn_measurement_method       'omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            5501
_diffrn_reflns_av_unetI/netI     0.0547
_diffrn_reflns_av_R_equivalents  0.0653
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         10.009
_diffrn_reflns_theta_max         72.529
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.937
_diffrn_measured_fraction_theta_full 0.942
_diffrn_reflns_Laue_measured_fraction_max 0.937
_diffrn_reflns_Laue_measured_fraction_full 0.942
_diffrn_reflns_point_group_measured_fraction_max 0.937
_diffrn_reflns_point_group_measured_fraction_full 0.942
_reflns_number_total             1285
_reflns_number_gt                1181
_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       'APEX 2, Bruker-AXS'
_computing_cell_refinement       'SAINT V8.35A, Bruker-AXS'
_computing_data_reduction        'SAINT V8.35A, Bruker-AXS'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_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)+(0.1204P)²+0.2844P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         1285
_refine_ls_number_parameters     109
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0679
_refine_ls_R_factor_gt           0.0647
_refine_ls_wR_factor_ref         0.1882
_refine_ls_wR_factor_gt          0.1823
_refine_ls_goodness_of_fit_ref   1.107
_refine_ls_restrained_S_all      1.107
_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 0.29492(13) 1.0648(3) 0.09997(12) 0.0326(5) Uani 1 1 d . . . . .
C1 C 0.35767(19) 0.8589(4) 0.14544(19) 0.0319(5) Uani 1 1 d . . . . .
O2 O 0.46361(15) 0.8367(3) 0.14529(17) 0.0437(5) Uani 1 1 d . . . . .
C2 C 0.17209(18) 1.0490(3) 0.10316(16) 0.0290(5) Uani 1 1 d . . . . .
O3 O 0.10425(14) 1.2125(3) 0.07010(13) 0.0357(5) Uani 1 1 d . . . . .
C3 C 0.27273(18) 0.6927(3) 0.18746(19) 0.0303(5) Uani 1 1 d . . . . .
H3 H 0.269914 0.534580 0.147320 0.036 Uiso 1 1 calc R U . . .
C4 C 0.14784(18) 0.8153(3) 0.15492(18) 0.0289(5) Uani 1 1 d . . . . .
H4 H 0.084543 0.720770 0.096477 0.035 Uiso 1 1 calc R U . . .
O4 O 0.17148(13) 0.6192(3) 0.33785(14) 0.0344(5) Uani 1 1 d . . . . .
C6 C 0.11818(18) 0.8366(4) 0.28368(19) 0.0310(6) Uani 1 1 d . . . . .
H6 H 0.029386 0.860017 0.282476 0.037 Uiso 1 1 calc R U . . .
C5 C 0.29521(19) 0.6695(4) 0.3295(2) 0.0333(6) Uani 1 1 d . . . . .
H5 H 0.358578 0.550624 0.368582 0.040 Uiso 1 1 calc R U . . .
C8 C 0.2051(2) 1.0196(4) 0.35424(18) 0.0342(6) Uani 1 1 d . . . . .
H8 H 0.185245 1.175277 0.374663 0.041 Uiso 1 1 calc R U . . .
C7 C 0.3146(2) 0.9174(4) 0.38161(18) 0.0365(6) Uani 1 1 d . . . . .
H7 H 0.389993 0.985474 0.425027 0.044 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 C2 1.388(2) . ?
O1 C1 1.393(3) . ?
C1 O2 1.193(3) . ?
C1 C3 1.494(3) . ?
C2 O3 1.198(3) . ?
C2 C4 1.497(3) . ?
C3 C4 1.525(3) . ?
C3 C5 1.573(3) . ?
C3 H3 1.0000 . ?
C4 C6 1.576(3) . ?
C4 H4 1.0000 . ?
O4 C6 1.438(2) . ?
O4 C5 1.440(3) . ?
C6 C8 1.510(3) . ?
C6 H6 1.0000 . ?
C5 C7 1.516(3) . ?
C5 H5 1.0000 . ?
C8 C7 1.324(3) . ?
C8 H8 0.9500 . ?
C7 H7 0.9500 . ?

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 110.56(15) . . ?
O2 C1 O1 120.02(19) . . ?
O2 C1 C3 130.1(2) . . ?
O1 C1 C3 109.91(17) . . ?
O3 C2 O1 120.00(18) . . ?
O3 C2 C4 129.99(19) . . ?
O1 C2 C4 109.98(16) . . ?
C1 C3 C4 104.72(16) . . ?
C1 C3 C5 114.89(17) . . ?
C4 C3 C5 101.33(15) . . ?
C1 C3 H3 111.7 . . ?
C4 C3 H3 111.7 . . ?
C5 C3 H3 111.7 . . ?
C2 C4 C3 104.71(15) . . ?
C2 C4 C6 113.15(16) . . ?
C3 C4 C6 101.35(15) . . ?
C2 C4 H4 112.3 . . ?
C3 C4 H4 112.3 . . ?
C6 C4 H4 112.3 . . ?
C6 O4 C5 96.32(14) . . ?
O4 C6 C8 102.25(16) . . ?
O4 C6 C4 99.84(15) . . ?
C8 C6 C4 106.82(15) . . ?
O4 C6 H6 115.3 . . ?
C8 C6 H6 115.3 . . ?
C4 C6 H6 115.3 . . ?
O4 C5 C7 101.96(17) . . ?
O4 C5 C3 99.45(15) . . ?
C7 C5 C3 107.07(16) . . ?
O4 C5 H5 115.5 . . ?
C7 C5 H5 115.5 . . ?
C3 C5 H5 115.5 . . ?
C7 C8 C6 105.49(18) . . ?
C7 C8 H8 127.3 . . ?
C6 C8 H8 127.3 . . ?
C8 C7 C5 105.96(18) . . ?
C8 C7 H7 127.0 . . ?
C5 C7 H7 127.0 . . ?

_refine_diff_density_max         0.264
_refine_diff_density_min         -0.246
_refine_diff_density_rms         0.065
####################################################################### 
# 
# 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_(endo-1)-100K
_database_code_depnum_ccdc_archive 'CCDC 2376893'
loop_
_audit_author_name
_audit_author_address
'Cameron Lennox'
;McGill University
Canada
;
_audit_update_record             
;
2024-11-06 deposited with the CCDC.	2026-05-12 downloaded from the CCDC.
;
_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        
'endo-7-oxabicyclo(2.2.1)-5-heptene-2,3-dicarboxylic anhydride'
_chemical_name_common            ?
_chemical_formula_moiety         'C8 H6 O4'
_chemical_formula_sum            'C8 H6 O4'
_chemical_properties_physical    moisture-sensitive
_exptl_crystal_recrystallization_method neat
_chemical_melting_point          ?
_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_diffrn_ambient_temperature      100(2)
_diffrn_ambient_pressure         1013
_chemical_formula_weight         166.13
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'

_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'
_chemical_absolute_configuration .
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'

_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.
;
_cell_length_a                   11.1845(9)
_cell_length_b                   5.6420(4)
_cell_length_c                   11.2971(9)
_cell_angle_alpha                90
_cell_angle_beta                 104.169(4)
_cell_angle_gamma                90
_cell_volume                     691.19(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    6655
_cell_measurement_theta_min      53.250
_cell_measurement_theta_max      141.052
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.596
_exptl_crystal_F_000             344
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.447
_exptl_crystal_size_mid          0.254
_exptl_crystal_size_min          0.182
_exptl_absorpt_coefficient_mu    1.122
_shelx_estimated_absorpt_T_min   0.634
_shelx_estimated_absorpt_T_max   0.822
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.4373
_exptl_absorpt_correction_T_max  0.7536
_exptl_absorpt_process_details   'SADABS-2012/1, G. Sheldrick'
_exptl_absorpt_special_details   ?
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   'sealed x-ray tube'
_diffrn_source_type              'Bruker D8 Advance'
_diffrn_measurement_device_type  'Bruker PHOTON 100 CMOS'
_diffrn_measurement_method       'omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            5260
_diffrn_reflns_av_unetI/netI     0.0554
_diffrn_reflns_av_R_equivalents  0.0648
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         10.013
_diffrn_reflns_theta_max         72.492
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.957
_diffrn_measured_fraction_theta_full 0.960
_diffrn_reflns_Laue_measured_fraction_max 0.957
_diffrn_reflns_Laue_measured_fraction_full 0.960
_diffrn_reflns_point_group_measured_fraction_max 0.957
_diffrn_reflns_point_group_measured_fraction_full 0.960
_reflns_number_total             1298
_reflns_number_gt                1201
_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       'APEX 2, Bruker-AXS'
_computing_cell_refinement       'SAINT V8.35A, Bruker-AXS'
_computing_data_reduction        'SAINT V8.35A, Bruker-AXS'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_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)+(0.1424P)²+0.2599P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         1298
_refine_ls_number_parameters     109
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0738
_refine_ls_R_factor_gt           0.0714
_refine_ls_wR_factor_ref         0.2072
_refine_ls_wR_factor_gt          0.2019
_refine_ls_goodness_of_fit_ref   1.119
_refine_ls_restrained_S_all      1.119
_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 0.29536(13) -0.0632(3) 0.10045(12) 0.0286(5) Uani 1 1 d . . . . .
C1 C 0.17207(18) -0.0475(3) 0.10310(17) 0.0264(5) Uani 1 1 d . . . . .
O2 O 0.10432(14) -0.2117(3) 0.07010(13) 0.0317(5) Uani 1 1 d . . . . .
C2 C 0.35837(19) 0.1425(4) 0.14619(18) 0.0283(6) Uani 1 1 d . . . . .
O3 O 0.46469(15) 0.1658(3) 0.14668(16) 0.0370(5) Uani 1 1 d . . . . .
C3 C 0.14751(18) 0.1869(3) 0.15509(18) 0.0262(6) Uani 1 1 d . . . . .
H3 H 0.084273 0.282003 0.096254 0.031 Uiso 1 1 calc R U . . .
C4 C 0.27326(19) 0.3091(3) 0.18864(19) 0.0271(6) Uani 1 1 d . . . . .
H4 H 0.270665 0.467994 0.148838 0.033 Uiso 1 1 calc R U . . .
O4 O 0.17091(13) 0.3821(3) 0.33864(13) 0.0302(5) Uani 1 1 d . . . . .
C5 C 0.11749(19) 0.1646(4) 0.28413(19) 0.0276(6) Uani 1 1 d . . . . .
H5 H 0.028455 0.141305 0.282425 0.033 Uiso 1 1 calc R U . . .
C7 C 0.2044(2) -0.0199(4) 0.35460(18) 0.0296(6) Uani 1 1 d . . . . .
H7 H 0.184326 -0.176115 0.374515 0.035 Uiso 1 1 calc R U . . .
C6 C 0.29498(19) 0.3312(4) 0.33097(19) 0.0293(6) Uani 1 1 d . . . . .
H6 H 0.358542 0.449911 0.370825 0.035 Uiso 1 1 calc R U . . .
C8 C 0.3142(2) 0.0821(4) 0.38274(19) 0.0318(6) Uani 1 1 d . . . . .
H8 H 0.389729 0.013367 0.426411 0.038 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 C1 1.389(2) . ?
O1 C2 1.390(3) . ?
C1 O2 1.197(3) . ?
C1 C3 1.499(3) . ?
C2 O3 1.195(3) . ?
C2 C4 1.498(3) . ?
C3 C4 1.529(3) . ?
C3 C5 1.579(3) . ?
C3 H3 1.0000 . ?
C4 C6 1.571(3) . ?
C4 H4 1.0000 . ?
O4 C5 1.436(2) . ?
O4 C6 1.440(2) . ?
C5 C7 1.511(3) . ?
C5 H5 1.0000 . ?
C7 C8 1.323(3) . ?
C7 H7 0.9500 . ?
C6 C8 1.517(3) . ?
C6 H6 1.0000 . ?
C8 H8 0.9500 . ?

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 C2 110.73(15) . . ?
O2 C1 O1 119.99(18) . . ?
O2 C1 C3 129.92(19) . . ?
O1 C1 C3 110.04(16) . . ?
O3 C2 O1 120.43(19) . . ?
O3 C2 C4 129.75(19) . . ?
O1 C2 C4 109.82(16) . . ?
C1 C3 C4 104.45(15) . . ?
C1 C3 C5 113.10(15) . . ?
C4 C3 C5 101.40(15) . . ?
C1 C3 H3 112.4 . . ?
C4 C3 H3 112.4 . . ?
C5 C3 H3 112.4 . . ?
C2 C4 C3 104.82(16) . . ?
C2 C4 C6 115.23(17) . . ?
C3 C4 C6 101.06(15) . . ?
C2 C4 H4 111.7 . . ?
C3 C4 H4 111.7 . . ?
C6 C4 H4 111.7 . . ?
C5 O4 C6 96.30(14) . . ?
O4 C5 C7 102.49(16) . . ?
O4 C5 C3 99.66(15) . . ?
C7 C5 C3 106.66(15) . . ?
O4 C5 H5 115.4 . . ?
C7 C5 H5 115.4 . . ?
C3 C5 H5 115.4 . . ?
C8 C7 C5 105.47(18) . . ?
C8 C7 H7 127.3 . . ?
C5 C7 H7 127.3 . . ?
O4 C6 C8 102.09(17) . . ?
O4 C6 C4 99.64(15) . . ?
C8 C6 C4 107.03(16) . . ?
O4 C6 H6 115.4 . . ?
C8 C6 H6 115.4 . . ?
C4 C6 H6 115.4 . . ?
C7 C8 C6 105.91(18) . . ?
C7 C8 H8 127.0 . . ?
C6 C8 H8 127.0 . . ?

_refine_diff_density_max         0.292
_refine_diff_density_min         -0.394
_refine_diff_density_rms         0.083
####################################################################### 
# 
# 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_(endo-1)-RT
_database_code_depnum_ccdc_archive 'CCDC 2376889'
loop_
_audit_author_name
_audit_author_address
'Cameron Lennox'
;McGill University
Canada
;
_audit_update_record             
;
2025-02-18 deposited with the CCDC.	2026-05-12 downloaded from the CCDC.
;
_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        
'endo-7-oxabicyclo(2.2.1)-5-heptene-2,3-dicarboxylic anhydride'
_chemical_name_common            ?
_chemical_formula_moiety         'C8 H6 O4'
_chemical_formula_sum            'C8 H6 O4'
_chemical_properties_physical    moisture-sensitive
_exptl_crystal_recrystallization_method neat
_chemical_melting_point          ?
_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_diffrn_ambient_temperature      298(2)
_diffrn_ambient_pressure         1013
_chemical_formula_weight         166.13
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'
O O 0.0492 0.0322 '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'

_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'
_chemical_absolute_configuration .
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'

_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.
;
_cell_length_a                   11.2763(6)
_cell_length_b                   5.7097(3)
_cell_length_c                   11.4279(6)
_cell_angle_alpha                90
_cell_angle_beta                 103.881(3)
_cell_angle_gamma                90
_cell_volume                     714.29(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    8915
_cell_measurement_theta_min      8.063
_cell_measurement_theta_max      143.728
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.545
_exptl_crystal_F_000             344
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_exptl_absorpt_coefficient_mu    1.086
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5648
_exptl_absorpt_correction_T_max  0.7536
_exptl_absorpt_process_details   'SADABS-2012/1, G. Sheldrick'
_exptl_absorpt_special_details   ?
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   'sealed x-ray tube'
_diffrn_source_type              'Bruker D8 Venture'
_diffrn_measurement_device_type  'Bruker PHOTON 100 CMOS'
_diffrn_measurement_method       'omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            7908
_diffrn_reflns_av_unetI/netI     0.0458
_diffrn_reflns_av_R_equivalents  0.0603
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         4.038
_diffrn_reflns_theta_max         72.434
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measured_fraction_theta_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_point_group_measured_fraction_full 0.992
_reflns_number_total             1389
_reflns_number_gt                1087
_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       'APEX 2, Bruker-AXS'
_computing_cell_refinement       'SAINT V8.35A, Bruker-AXS'
_computing_data_reduction        'SAINT V8.35A, Bruker-AXS'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_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)+(0.0663P)²+0.1798P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         1389
_refine_ls_number_parameters     109
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0582
_refine_ls_R_factor_gt           0.0464
_refine_ls_wR_factor_ref         0.1377
_refine_ls_wR_factor_gt          0.1234
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_restrained_S_all      1.029
_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 0.29300(12) -0.0707(3) 0.09924(11) 0.0651(4) Uani 1 1 d . . . . .
C1 C 0.17193(18) -0.0543(4) 0.10311(14) 0.0586(5) Uani 1 1 d . . . . .
O2 O 0.10440(15) -0.2148(3) 0.07066(13) 0.0743(5) Uani 1 1 d . . . . .
C2 C 0.35550(19) 0.1334(4) 0.14201(17) 0.0634(5) Uani 1 1 d . . . . .
O3 O 0.45982(15) 0.1545(3) 0.14150(16) 0.0884(6) Uani 1 1 d . . . . .
C3 C 0.27183(18) 0.2986(4) 0.18407(17) 0.0608(5) Uani 1 1 d . . . . .
H3 H 0.267904 0.450922 0.143765 0.073 Uiso 1 1 calc R U . . .
C4 C 0.14933(17) 0.1766(3) 0.15508(16) 0.0579(5) Uani 1 1 d . . . . .
H4 H 0.086926 0.267759 0.099015 0.069 Uiso 1 1 calc R U . . .
O4 O 0.17375(13) 0.3747(3) 0.33428(13) 0.0710(5) Uani 1 1 d . . . . .
C6 C 0.29572(19) 0.3258(4) 0.32466(19) 0.0682(6) Uani 1 1 d . . . . .
H6 H 0.357371 0.442322 0.361070 0.082 Uiso 1 1 calc R U . . .
C5 C 0.12198(19) 0.1588(4) 0.28370(18) 0.0633(5) Uani 1 1 d . . . . .
H5 H 0.035930 0.135435 0.283896 0.076 Uiso 1 1 calc R U . . .
C7 C 0.3158(2) 0.0833(5) 0.37739(16) 0.0752(6) Uani 1 1 d . . . . .
H7 H 0.389568 0.018521 0.418989 0.090 Uiso 1 1 calc R U . . .
C8 C 0.2081(2) -0.0182(4) 0.35276(17) 0.0718(6) Uani 1 1 d . . . . .
H8 H 0.189552 -0.168722 0.373951 0.086 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 C1 1.380(2) . ?
O1 C2 1.389(3) . ?
C1 O2 1.192(2) . ?
C1 C4 1.493(3) . ?
C2 O3 1.184(3) . ?
C2 C3 1.493(3) . ?
C3 C4 1.511(3) . ?
C3 C6 1.572(3) . ?
C3 H3 0.9800 . ?
C4 C5 1.576(3) . ?
C4 H4 0.9800 . ?
O4 C5 1.425(2) . ?
O4 C6 1.433(3) . ?
C6 C7 1.505(3) . ?
C6 H6 0.9800 . ?
C5 C8 1.490(3) . ?
C5 H5 0.9800 . ?
C7 C8 1.314(3) . ?
C7 H7 0.9300 . ?
C8 H8 0.9300 . ?

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 C2 110.76(15) . . ?
O2 C1 O1 120.06(18) . . ?
O2 C1 C4 130.19(19) . . ?
O1 C1 C4 109.71(16) . . ?
O3 C2 O1 120.3(2) . . ?
O3 C2 C3 130.0(2) . . ?
O1 C2 C3 109.69(17) . . ?
C2 C3 C4 104.65(17) . . ?
C2 C3 C6 115.14(17) . . ?
C4 C3 C6 101.13(14) . . ?
C2 C3 H3 111.7 . . ?
C4 C3 H3 111.7 . . ?
C6 C3 H3 111.7 . . ?
C1 C4 C3 105.08(16) . . ?
C1 C4 C5 113.86(16) . . ?
C3 C4 C5 101.44(14) . . ?
C1 C4 H4 111.9 . . ?
C3 C4 H4 111.9 . . ?
C5 C4 H4 111.9 . . ?
C5 O4 C6 96.18(14) . . ?
O4 C6 C7 101.74(17) . . ?
O4 C6 C3 99.52(15) . . ?
C7 C6 C3 106.92(16) . . ?
O4 C6 H6 115.5 . . ?
C7 C6 H6 115.5 . . ?
C3 C6 H6 115.5 . . ?
O4 C5 C8 102.73(17) . . ?
O4 C5 C4 99.78(15) . . ?
C8 C5 C4 106.81(15) . . ?
O4 C5 H5 115.2 . . ?
C8 C5 H5 115.2 . . ?
C4 C5 H5 115.2 . . ?
C8 C7 C6 106.1(2) . . ?
C8 C7 H7 126.9 . . ?
C6 C7 H7 126.9 . . ?
C7 C8 C5 105.4(2) . . ?
C7 C8 H8 127.3 . . ?
C5 C8 H8 127.3 . . ?

_refine_diff_density_max         0.166
_refine_diff_density_min         -0.183
_refine_diff_density_rms         0.041
####################################################################### 
# 
# 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_(endo-1)(exo-1)_150
_database_code_depnum_ccdc_archive 'CCDC 2376888'
loop_
_audit_author_name
_audit_author_address
'Cameron Lennox'
;McGill University
Canada
;
_audit_update_record             
;
2024-08-11 deposited with the CCDC.	2026-05-12 downloaded from the CCDC.
;
_audit_creation_date             2024-05-30
_audit_creation_method           
;
Olex2 1.5
(compiled 2024.01.12 svn.r2f8d729c for OlexSys, GUI svn.r6928)
;
_shelx_SHELXL_version_number     2018/3
# end Validation Reply Form
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '2(C8 H6 O4)'
_chemical_formula_sum            'C16 H12 O8'
_chemical_formula_weight         332.26
_chemical_absolute_configuration ?
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C15 H11 N2 O7'
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           7
_space_group_name_H-M_alt        'P 1 n 1'
_space_group_name_Hall           'P -2yac'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'x+1/2, -y, z+1/2'

_cell_length_a                   11.8895(13)
_cell_length_b                   5.3562(4)
_cell_length_c                   11.8978(13)
_cell_angle_alpha                90
_cell_angle_beta                 110.247(12)
_cell_angle_gamma                90
_cell_volume                     710.86(13)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    5444
_cell_measurement_temperature    150.00(10)
_cell_measurement_theta_max      76.4000
_cell_measurement_theta_min      4.4820
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    1.091
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.84568
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.43.116a (Rigaku Oxford Diffraction, 2024)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.552
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             344
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.123
_exptl_crystal_size_min          0.109
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0577
_diffrn_reflns_av_unetI/netI     0.0396
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            11733
_diffrn_reflns_point_group_measured_fraction_full 0.953
_diffrn_reflns_point_group_measured_fraction_max 0.928
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.261
_diffrn_reflns_theta_min         3.960
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      150.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.1768
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -51.00 -12.00   1.00    1.00    --  -39.71 -57.00 -86.00   39
  2  ω   -111.00 -60.00   1.00    1.00    --  -39.71 -57.00 -86.00   51
  3  ω     38.00  63.00   1.00    1.00    --   39.71  57.00  55.00   25
  4  ω     84.00 109.00   1.00    1.00    --  113.00  57.00  55.00   25
  5  ω    142.00 169.00   1.00    1.00    --  113.00  57.00  55.00   27
  6  ω    107.00 134.00   1.00    1.00    --  113.00 -57.00 -86.00   27
  7  ω    -43.00 -13.00   1.00    1.00    --  -39.71 -38.00 -90.00   30
  8  ω    -54.00  34.00   1.00    1.00    --  -39.71  57.00  55.00   88
  9  ω    -69.00   6.00   1.00    1.00    --  -39.71  57.00-150.00   75
 10  ω      3.00  31.00   1.00    1.00    --   39.71  87.00 108.26   28
 11  ω     31.00  86.00   1.00    1.00    --   39.71-125.00 120.00   55
 12  ω      7.00  79.00   1.00    1.00    --   39.71 -99.00-120.00   72
 13  ω    -26.00  54.00   1.00    1.00    --   39.71 -57.00 -86.00   80
 14  ω      3.00  28.00   1.00    1.00    --   40.00  89.00 -72.53   25
 15  ω     14.00  39.00   1.00    1.00    --   48.00  79.00-126.74   25
 16  ω     14.00  41.00   1.00    1.00    --   48.00  78.00  79.38   27
 17  ω     13.00  38.00   1.00    1.00    --   48.00  81.00   6.08   25
 18  ω     15.00  40.00   1.00    1.00    --   48.00  79.00 178.45   25
 19  ω     29.00  77.00   1.00    1.00    --   56.00  68.00 -40.16   48
 20  ω     24.00 110.00   1.00    1.00    --   56.00  68.00  50.52   86
 21  ω     32.00  88.00   1.00    1.00    --   60.00  68.00 142.14   56
 22  ω     91.00 124.00   1.00    1.00    --   60.00  68.00 142.14   33
 23  ω     31.00  70.00   1.00    1.00    --   60.00  68.00 -71.22   39
 24  ω     34.00  67.00   1.00    1.00    --   64.00  61.00-160.37   33
 25  ω     37.00  79.00   1.00    1.00    --   68.00  70.00 102.61   42
 26  ω     38.00  89.00   1.00    1.00    --   68.00  70.00-151.19   51
 27  ω     37.00 140.00   1.00    1.00    --   68.00  71.00 -16.62  103
 28  ω    121.00 148.00   1.00    1.00    --   72.00  69.00-120.49   27
 29  ω     43.00  72.00   1.00    1.00    --   72.00  69.00-120.49   29
 30  ω     46.00 107.00   1.00    1.00    --   76.00  63.00  71.04   61
 31  ω     29.00 101.00   1.00    1.00    --  113.00 -94.00-180.00   72
 32  ω    121.00 165.00   1.00    1.00    --  113.00  61.00  30.00   44
 33  ω     84.00 113.00   1.00    1.00    --  113.00  61.00  30.00   29
 34  ω     84.00 151.00   1.00    1.00    --  113.00  61.00 -60.00   67
 35  ω     85.00 126.00   1.00    1.00    --  113.00  61.00 120.00   41
 36  ω    133.00 162.00   1.00    1.00    --  113.00  61.00 120.00   29
 37  ω     89.00 145.00   1.00    1.00    --  113.00  45.00 -90.00   56
 38  ω     83.00 177.00   1.00    1.00    --  113.00  61.00  90.00   94
 39  ω    128.00 177.00   1.00    1.00    --  113.00  61.00-180.00   49
 40  ω    117.00 175.00   1.00    1.00    --  113.00  61.00   0.00   58
 41  ω     66.00 109.00   1.00    1.00    --  113.00-111.00 -90.00   43
 42  ω     38.00  91.00   1.00    1.00    --  113.00-111.00 120.00   53
 43  ω     83.00 115.00   1.00    1.00    --  113.00  61.00-180.00   32
 44  ω     85.00 174.00   1.00    1.00    --  113.00  61.00 -30.00   89
 45  ω     83.00 111.00   1.00    1.00    --  113.00  61.00   0.00   28
 46  ω    117.00 155.00   1.00    1.00    --  113.00  61.00-120.00   38
 47  ω     83.00 109.00   1.00    1.00    --  113.00  61.00-120.00   26
 48  ω     87.00 114.00   1.00    1.00    --  113.00  45.00-120.00   27
 49  ω     88.00 113.00   1.00    1.00    --  113.00  45.00 120.00   25
 50  ω     31.00 106.00   1.00    1.00    --  113.00 -94.00   0.00   75
 51  ω    130.00 155.00   1.00    1.00    --  113.00  61.00-150.00   25
 52  ω     86.00 123.00   1.00    1.00    --  113.00  45.00  90.00   37
 53  ω     43.00 116.00   1.00    1.00    --  113.00 -45.00-180.00   73
 54  ω     38.00  86.00   1.00    1.00    --  113.00-111.00  90.00   48
 55  ω     84.00 114.00   1.00    1.00    --  113.00  61.00-150.00   30
 56  ω     83.00 173.00   1.00    1.00    --  113.00  61.00 150.00   90
 57  ω     83.00 178.00   1.00    1.00    --  113.00  61.00 -90.00   95
 58  ω     41.00 107.00   1.00    1.00    --  113.00-111.00 150.00   66
 59  ω     58.00 109.00   1.00    1.00    --  113.00-111.00 -30.00   51
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0542213000
_diffrn_orient_matrix_UB_12      0.1064544000
_diffrn_orient_matrix_UB_13      -0.0903432000
_diffrn_orient_matrix_UB_21      -0.0349393000
_diffrn_orient_matrix_UB_22      0.2656187000
_diffrn_orient_matrix_UB_23      0.0252839000
_diffrn_orient_matrix_UB_31      0.1220729000
_diffrn_orient_matrix_UB_32      0.0288217000
_diffrn_orient_matrix_UB_33      0.1012102000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.874
_reflns_Friedel_fraction_full    0.906
_reflns_Friedel_fraction_max     0.867
_reflns_number_gt                2605
_reflns_number_total             2803
_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. Completness statistics refer to single and
 composite reflections containing twin component 1 only.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.43.116a (Rigaku OD, 2024)'
_computing_data_collection       
'CrysAlisPro system (CCD 43.116a 64-bit (release 22-03-2024))'
_computing_data_reduction        'CrysAlisPro 1.171.43.116a (Rigaku OD, 2024)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    ?
_refine_diff_density_max         0.185
_refine_diff_density_min         -0.195
_refine_diff_density_rms         0.047
_refine_ls_abs_structure_details 
;
 Flack x determined using 1097 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.1(2)
_refine_ls_extinction_coef       0.0092(11)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.099
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     219
_refine_ls_number_reflns         2803
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0509
_refine_ls_R_factor_gt           0.0459
_refine_ls_restrained_S_all      1.099
_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)+(0.0354P)²+0.5545P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1065
_refine_ls_wR_factor_ref         0.1123
_refine_special_details          
;
 Refined as a 2-component twin.
;
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 0.54822
 0.45178
2.a Ternary CH refined with riding coordinates:
 C11(H11), C12(H12), C13(H13), C14(H14), C3(H3), C4(H4), C5(H5), C6(H6)
2.b Aromatic/amide H refined with riding coordinates:
 C15(H15), C16(H16), C7(H7), C8(H8)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_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 0.5006(4) 0.9113(8) 0.3503(4) 0.0325(10) Uani 1 1 d . . . . .
C9 C 0.5576(6) 0.4142(12) 0.6297(6) 0.0360(16) Uani 1 1 d . . . . .
C10 C 0.6093(6) 0.4028(12) 0.8315(6) 0.0300(14) Uani 1 1 d . . . . .
C11 C 0.5151(6) 0.1617(11) 0.6530(6) 0.0307(14) Uani 1 1 d . . . . .
H11 H 0.550171 0.019738 0.621566 0.037 Uiso 1 1 calc R U . . .
C12 C 0.5466(6) 0.1581(11) 0.7891(6) 0.0284(14) Uani 1 1 d . . . . .
H12 H 0.596676 0.010717 0.827857 0.034 Uiso 1 1 calc R U . . .
C13 C 0.3742(6) 0.1587(12) 0.6098(6) 0.0318(15) Uani 1 1 d . . . . .
H13 H 0.331834 0.214569 0.525487 0.038 Uiso 1 1 calc R U . . .
C14 C 0.4189(6) 0.1548(12) 0.8021(6) 0.0319(15) Uani 1 1 d . . . . .
H14 H 0.416050 0.207286 0.881732 0.038 Uiso 1 1 calc R U . . .
C15 C 0.3403(6) -0.0978(12) 0.6412(7) 0.0358(16) Uani 1 1 d . . . . .
H15 H 0.305527 -0.229723 0.586883 0.043 Uiso 1 1 calc R U . . .
C16 C 0.3685(6) -0.1024(12) 0.7585(6) 0.0336(16) Uani 1 1 d . . . . .
H16 H 0.359135 -0.238121 0.805924 0.040 Uiso 1 1 calc R U . . .
O8 O 0.3540(4) 0.3096(8) 0.7018(4) 0.0344(10) Uani 1 1 d . . . . .
O7 O 0.6507(5) 0.4859(10) 0.9295(5) 0.0411(12) Uani 1 1 d . . . . .
O6 O 0.5506(5) 0.5079(11) 0.5366(5) 0.0492(14) Uani 1 1 d . . . . .
O5 O 0.6090(4) 0.5462(8) 0.7341(4) 0.0345(10) Uani 1 1 d . . . . .
C2 C 0.5996(6) 0.7746(12) 0.3491(6) 0.0328(15) Uani 1 1 d . . . . .
C3 C 0.4225(6) 0.5262(12) 0.2572(6) 0.0312(14) Uani 1 1 d . . . . .
H3 H 0.396187 0.383890 0.296593 0.037 Uiso 1 1 calc R U . . .
C4 C 0.5604(6) 0.5283(12) 0.2875(6) 0.0309(14) Uani 1 1 d . . . . .
H4 H 0.600227 0.384286 0.339606 0.037 Uiso 1 1 calc R U . . .
C5 C 0.3774(7) 0.4975(13) 0.1185(7) 0.0366(17) Uani 1 1 d . . . . .
H5 H 0.293735 0.432849 0.081234 0.044 Uiso 1 1 calc R U . . .
C6 C 0.5684(6) 0.5080(12) 0.1598(6) 0.0319(15) Uani 1 1 d . . . . .
H6 H 0.647818 0.452662 0.157280 0.038 Uiso 1 1 calc R U . . .
C7 C 0.4023(8) 0.7417(14) 0.0701(7) 0.0431(19) Uani 1 1 d . . . . .
H7 H 0.345444 0.865485 0.029717 0.052 Uiso 1 1 calc R U . . .
C8 C 0.5215(8) 0.7495(12) 0.0957(6) 0.0393(17) Uani 1 1 d . . . . .
H8 H 0.566660 0.879594 0.077297 0.047 Uiso 1 1 calc R U . . .
O4 O 0.4705(5) 0.3382(8) 0.1064(5) 0.0395(12) Uani 1 1 d . . . . .
C1 C 0.3958(6) 0.7751(13) 0.3013(6) 0.0351(15) Uani 1 1 d . . . . .
O3 O 0.6982(5) 0.8607(9) 0.3926(5) 0.0428(13) Uani 1 1 d . . . . .
O2 O 0.3019(5) 0.8657(9) 0.2963(6) 0.0496(14) 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 1.390(8) . ?
O1 C1 1.386(9) . ?
C9 C11 1.503(8) . ?
C9 O6 1.193(8) . ?
C9 O5 1.376(9) . ?
C10 C12 1.506(9) . ?
C10 O7 1.185(9) . ?
C10 O5 1.389(8) . ?
C11 H11 1.0000 . ?
C11 C12 1.531(9) . ?
C11 C13 1.573(10) . ?
C12 H12 1.0000 . ?
C12 C14 1.578(9) . ?
C13 H13 1.0000 . ?
C13 C15 1.514(8) . ?
C13 O8 1.446(8) . ?
C14 H14 1.0000 . ?
C14 C16 1.520(9) . ?
C14 O8 1.439(8) . ?
C15 H15 0.9500 . ?
C15 C16 1.318(10) . ?
C16 H16 0.9500 . ?
C2 C4 1.503(9) . ?
C2 O3 1.198(8) . ?
C3 H3 1.0000 . ?
C3 C4 1.552(9) . ?
C3 C5 1.556(10) . ?
C3 C1 1.507(9) . ?
C4 H4 1.0000 . ?
C4 C6 1.559(9) . ?
C5 H5 1.0000 . ?
C5 C7 1.499(11) . ?
C5 O4 1.444(9) . ?
C6 H6 1.0000 . ?
C6 C8 1.507(9) . ?
C6 O4 1.440(8) . ?
C7 H7 0.9500 . ?
C7 C8 1.344(12) . ?
C8 H8 0.9500 . ?
C1 O2 1.199(8) . ?

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 C2 111.1(5) . . ?
O6 C9 C11 129.1(7) . . ?
O6 C9 O5 119.3(6) . . ?
O5 C9 C11 111.6(6) . . ?
O7 C10 C12 130.2(6) . . ?
O7 C10 O5 119.5(6) . . ?
O5 C10 C12 110.2(5) . . ?
C9 C11 H11 113.9 . . ?
C9 C11 C12 103.4(5) . . ?
C9 C11 C13 109.7(5) . . ?
C12 C11 H11 113.9 . . ?
C12 C11 C13 100.8(5) . . ?
C13 C11 H11 113.9 . . ?
C10 C12 C11 104.7(5) . . ?
C10 C12 H12 112.7 . . ?
C10 C12 C14 111.0(5) . . ?
C11 C12 H12 112.7 . . ?
C11 C12 C14 102.3(6) . . ?
C14 C12 H12 112.7 . . ?
C11 C13 H13 115.7 . . ?
C15 C13 C11 105.8(5) . . ?
C15 C13 H13 115.7 . . ?
O8 C13 C11 100.6(5) . . ?
O8 C13 H13 115.7 . . ?
O8 C13 C15 101.1(6) . . ?
C12 C14 H14 116.0 . . ?
C16 C14 C12 104.8(5) . . ?
C16 C14 H14 116.0 . . ?
O8 C14 C12 99.8(5) . . ?
O8 C14 H14 116.0 . . ?
O8 C14 C16 101.8(5) . . ?
C13 C15 H15 126.7 . . ?
C16 C15 C13 106.6(6) . . ?
C16 C15 H15 126.7 . . ?
C14 C16 H16 127.2 . . ?
C15 C16 C14 105.7(6) . . ?
C15 C16 H16 127.2 . . ?
C14 O8 C13 97.1(5) . . ?
C9 O5 C10 109.9(5) . . ?
O1 C2 C4 110.3(5) . . ?
O3 C2 O1 119.9(6) . . ?
O3 C2 C4 129.8(6) . . ?
C4 C3 H3 111.9 . . ?
C4 C3 C5 101.3(5) . . ?
C5 C3 H3 111.9 . . ?
C1 C3 H3 111.9 . . ?
C1 C3 C4 104.2(5) . . ?
C1 C3 C5 114.8(6) . . ?
C2 C4 C3 104.1(5) . . ?
C2 C4 H4 112.0 . . ?
C2 C4 C6 115.0(6) . . ?
C3 C4 H4 112.0 . . ?
C3 C4 C6 100.9(5) . . ?
C6 C4 H4 112.0 . . ?
C3 C5 H5 115.5 . . ?
C7 C5 C3 106.2(6) . . ?
C7 C5 H5 115.5 . . ?
O4 C5 C3 99.7(5) . . ?
O4 C5 H5 115.5 . . ?
O4 C5 C7 102.5(6) . . ?
C4 C6 H6 115.3 . . ?
C8 C6 C4 107.3(5) . . ?
C8 C6 H6 115.3 . . ?
O4 C6 C4 99.3(5) . . ?
O4 C6 H6 115.3 . . ?
O4 C6 C8 102.6(6) . . ?
C5 C7 H7 127.1 . . ?
C8 C7 C5 105.9(7) . . ?
C8 C7 H7 127.1 . . ?
C6 C8 H8 127.3 . . ?
C7 C8 C6 105.3(6) . . ?
C7 C8 H8 127.3 . . ?
C6 O4 C5 96.5(5) . . ?
O1 C1 C3 110.2(5) . . ?
O2 C1 O1 119.6(6) . . ?
O2 C1 C3 130.2(7) . . ?

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 C2 C4 C3 -3.2(7) . . . . ?
O1 C2 C4 C6 106.3(6) . . . . ?
C9 C11 C12 C10 -2.6(7) . . . . ?
C9 C11 C12 C14 113.2(5) . . . . ?
C9 C11 C13 C15 -177.9(6) . . . . ?
C9 C11 C13 O8 -73.0(6) . . . . ?
C10 C12 C14 C16 -179.0(6) . . . . ?
C10 C12 C14 O8 75.9(6) . . . . ?
C11 C9 O5 C10 1.6(7) . . . . ?
C11 C12 C14 C16 69.7(6) . . . . ?
C11 C12 C14 O8 -35.3(5) . . . . ?
C11 C13 C15 C16 72.6(7) . . . . ?
C11 C13 O8 C14 -59.7(5) . . . . ?
C12 C10 O5 C9 -3.4(7) . . . . ?
C12 C11 C13 C15 -69.2(6) . . . . ?
C12 C11 C13 O8 35.7(5) . . . . ?
C12 C14 C16 C15 -73.0(6) . . . . ?
C12 C14 O8 C13 58.8(5) . . . . ?
C13 C11 C12 C10 -116.1(5) . . . . ?
C13 C11 C12 C14 -0.2(5) . . . . ?
C13 C15 C16 C14 0.9(7) . . . . ?
C15 C13 O8 C14 49.0(6) . . . . ?
C16 C14 O8 C13 -48.7(6) . . . . ?
O8 C13 C15 C16 -31.9(7) . . . . ?
O8 C14 C16 C15 30.7(7) . . . . ?
O7 C10 C12 C11 -179.8(7) . . . . ?
O7 C10 C12 C14 70.6(10) . . . . ?
O7 C10 O5 C9 179.7(7) . . . . ?
O6 C9 C11 C12 -178.1(7) . . . . ?
O6 C9 C11 C13 -71.2(9) . . . . ?
O6 C9 O5 C10 -179.4(6) . . . . ?
O5 C9 C11 C12 0.8(7) . . . . ?
O5 C9 C11 C13 107.7(6) . . . . ?
O5 C10 C12 C11 3.8(7) . . . . ?
O5 C10 C12 C14 -105.9(6) . . . . ?
C2 O1 C1 C3 -2.6(7) . . . . ?
C2 O1 C1 O2 179.6(7) . . . . ?
C2 C4 C6 C8 -42.8(8) . . . . ?
C2 C4 C6 O4 -149.2(5) . . . . ?
C3 C4 C6 C8 68.5(6) . . . . ?
C3 C4 C6 O4 -37.9(6) . . . . ?
C3 C5 C7 C8 73.0(7) . . . . ?
C3 C5 O4 C6 -60.7(6) . . . . ?
C4 C3 C5 C7 -71.1(7) . . . . ?
C4 C3 C5 O4 35.1(6) . . . . ?
C4 C3 C1 O1 0.5(7) . . . . ?
C4 C3 C1 O2 178.0(8) . . . . ?
C4 C6 C8 C7 -72.9(7) . . . . ?
C4 C6 O4 C5 61.7(6) . . . . ?
C5 C3 C4 C2 121.1(5) . . . . ?
C5 C3 C4 C6 1.5(6) . . . . ?
C5 C3 C1 O1 -109.4(7) . . . . ?
C5 C3 C1 O2 68.1(10) . . . . ?
C5 C7 C8 C6 0.1(8) . . . . ?
C7 C5 O4 C6 48.4(7) . . . . ?
C8 C6 O4 C5 -48.4(6) . . . . ?
O4 C5 C7 C8 -31.1(8) . . . . ?
O4 C6 C8 C7 31.1(7) . . . . ?
C1 O1 C2 C4 3.7(7) . . . . ?
C1 O1 C2 O3 -177.0(6) . . . . ?
C1 C3 C4 C2 1.5(7) . . . . ?
C1 C3 C4 C6 -118.0(6) . . . . ?
C1 C3 C5 C7 40.5(8) . . . . ?
C1 C3 C5 O4 146.8(5) . . . . ?
O3 C2 C4 C3 177.6(7) . . . . ?
O3 C2 C4 C6 -72.9(9) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.447
_oxdiff_exptl_absorpt_empirical_full_min 0.716
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 0.54822
2 0.45178

# start Validation Reply Form
_vrf_PLAT340_cocrystal_150_200524_pn_new 
;
PROBLEM: Low Bond Precision on  C-C Bonds ...............    0.01006 Ang.  
RESPONSE: This is related to crystal twinning.
;
####################################################################### 
# 
# 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_(endo-1)(exo-1)-298K
_database_code_depnum_ccdc_archive 'CCDC 2376885'
loop_
_audit_author_name
_audit_author_address
'Cameron Lennox'
;McGill University
Canada
;
_audit_update_record             
;
2024-11-06 deposited with the CCDC.	2026-05-12 downloaded from the CCDC.
;
_audit_creation_date             2023-09-11
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        
'7-oxabicyclo(2.2.1)-5-heptene-2,3-dicarboxylic anhydride cocrystal'
_chemical_formula_moiety         'C8 H6 O4'
_chemical_formula_sum            'C16 H12 O8'
_chemical_formula_weight         332.2660
_chemical_absolute_configuration ?
_chemical_melting_point          ?
_chemical_properties_physical    moisture-sensitive
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'
O O 0.0492 0.0322 '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'

_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           7
_space_group_name_H-M_alt        'P 1 n 1'
_space_group_name_Hall           'P -2yac'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'x+1/2, -y, z+1/2'

_cell_length_a                   11.9547(5)
_cell_length_b                   5.4149(2)
_cell_length_c                   12.0064(5)
_cell_angle_alpha                90
_cell_angle_beta                 110.600(2)
_cell_angle_gamma                90
_cell_volume                     727.52(5)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    6752
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      144.348
_cell_measurement_theta_min      8.986
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    1.066
_exptl_absorpt_correction_T_max  0.7536
_exptl_absorpt_correction_T_min  0.6385
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS-2012/1, G. Sheldrick'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.517
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             344
_exptl_crystal_recrystallization_method neat
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0660
_diffrn_reflns_av_unetI/netI     0.0760
_diffrn_reflns_Laue_measured_fraction_full 0.965
_diffrn_reflns_Laue_measured_fraction_max 0.960
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            5522
_diffrn_reflns_point_group_measured_fraction_full 0.794
_diffrn_reflns_point_group_measured_fraction_max 0.774
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         72.401
_diffrn_reflns_theta_min         4.489
_diffrn_ambient_pressure         1013
_diffrn_ambient_temperature      298(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.965
_diffrn_measured_fraction_theta_max 0.960
_diffrn_measurement_device_type  'Bruker PHOTON 100 CMOS'
_diffrn_measurement_method       'omega scans'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   'sealed x-ray tube'
_diffrn_source_type              'Bruker D8 Venture'
_reflns_Friedel_coverage         0.609
_reflns_Friedel_fraction_full    0.621
_reflns_Friedel_fraction_max     0.587
_reflns_number_gt                1908
_reflns_number_total             2231
_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 V8.35A, Bruker-AXS'
_computing_data_collection       'APEX 2, Bruker-AXS'
_computing_data_reduction        'SAINT V8.35A, Bruker-AXS'
_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, 2018)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.390
_refine_diff_density_min         -0.358
_refine_diff_density_rms         0.089
_refine_ls_abs_structure_details 
;
 Flack x determined using 681 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.24(16)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.149
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     217
_refine_ls_number_reflns         2231
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0960
_refine_ls_R_factor_gt           0.0448
_refine_ls_restrained_S_all      1.148
_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)+(0.0820P)²+0.2428P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1199
_refine_ls_wR_factor_ref         0.1627
_refine_special_details          ?
_olex2_refinement_description    
;
1.a Ternary CH refined with riding coordinates:
 C3(H3), C4(H4), C5(H5), C6(H6), C11(H11), C12(H12), C13(H13), C14(H14)
1.b Aromatic/amide H refined with riding coordinates:
 C7(H7), C8(H8), C15(H15), C16(H16)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_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 0.2667(4) 0.9119(6) 0.3806(4) 0.0512(9) Uani 1 1 d . . . . .
C1 C 0.3704(5) 0.7782(10) 0.4314(5) 0.0538(13) Uani 1 1 d . . . . .
O8 O 0.9125(3) 0.6890(6) 0.5320(4) 0.0528(9) Uani 1 1 d . . . . .
O2 O 0.4644(4) 0.8666(10) 0.4378(5) 0.0845(16) Uani 1 1 d . . . . .
C2 C 0.1703(5) 0.7793(10) 0.3844(5) 0.0526(13) Uani 1 1 d . . . . .
O3 O 0.0724(4) 0.8653(10) 0.3407(5) 0.0766(14) Uani 1 1 d . . . . .
C3 C 0.3428(5) 0.5343(9) 0.4748(5) 0.0491(12) Uani 1 1 d . . . . .
H3 H 0.367959 0.394859 0.437091 0.059 Uiso 1 1 calc R U . . .
C4 C 0.2074(5) 0.5400(9) 0.4448(5) 0.0467(12) Uani 1 1 d . . . . .
H4 H 0.167540 0.401002 0.393998 0.056 Uiso 1 1 calc R U . . .
O4 O 0.2974(4) 0.3526(7) 0.6270(4) 0.0643(11) Uani 1 1 d . . . . .
O5 O 0.6601(4) 0.4586(6) 0.5000(4) 0.0542(9) Uani 1 1 d . . . . .
C5 C 0.3891(6) 0.5098(12) 0.6153(6) 0.0633(17) Uani 1 1 d . . . . .
H5 H 0.471118 0.449458 0.652732 0.076 Uiso 1 1 calc R U . . .
O6 O 0.6189(5) 0.5152(9) 0.3060(4) 0.0737(13) Uani 1 1 d . . . . .
C6 C 0.2004(5) 0.5195(10) 0.5731(5) 0.0529(14) Uani 1 1 d . . . . .
H6 H 0.122916 0.466163 0.575463 0.064 Uiso 1 1 calc R U . . .
C7 C 0.3620(7) 0.7512(13) 0.6611(6) 0.0723(19) Uani 1 1 d . . . . .
H7 H 0.416357 0.873870 0.699422 0.087 Uiso 1 1 calc R U . . .
O7 O 0.7159(5) 0.4981(11) 0.6943(4) 0.0821(15) Uani 1 1 d . . . . .
C8 C 0.2467(7) 0.7545(11) 0.6363(5) 0.0611(16) Uani 1 1 d . . . . .
H8 H 0.202353 0.879089 0.654430 0.073 Uiso 1 1 calc R U . . .
C9 C 0.6595(5) 0.5989(9) 0.4034(5) 0.0486(12) Uani 1 1 d . . . . .
C10 C 0.7104(6) 0.5886(10) 0.6038(6) 0.0582(15) Uani 1 1 d . . . . .
C11 C 0.7208(5) 0.8401(8) 0.4438(5) 0.0433(11) Uani 1 1 d . . . . .
H11 H 0.671618 0.982942 0.406291 0.052 Uiso 1 1 calc R U . . .
C12 C 0.7552(5) 0.8350(9) 0.5803(5) 0.0463(12) Uani 1 1 d . . . . .
H12 H 0.722013 0.973867 0.610946 0.056 Uiso 1 1 calc R U . . .
C13 C 0.8479(5) 0.8445(9) 0.4338(5) 0.0498(13) Uani 1 1 d . . . . .
H13 H 0.850841 0.794286 0.356485 0.060 Uiso 1 1 calc R U . . .
C14 C 0.8942(5) 0.8383(9) 0.6233(5) 0.0502(12) Uani 1 1 d . . . . .
H14 H 0.935642 0.782600 0.705228 0.060 Uiso 1 1 calc R U . . .
C15 C 0.9006(5) 1.0959(10) 0.4775(6) 0.0544(14) Uani 1 1 d . . . . .
H15 H 0.910890 1.225969 0.431394 0.065 Uiso 1 1 calc R U . . .
C16 C 0.9288(5) 1.0933(9) 0.5936(5) 0.0523(13) Uani 1 1 d . . . . .
H16 H 0.962839 1.220859 0.646490 0.063 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 C1 1.378(7) . ?
O1 C2 1.372(7) . ?
C1 O2 1.199(7) . ?
C1 C3 1.498(7) . ?
O8 C13 1.433(7) . ?
O8 C14 1.440(7) . ?
C2 O3 1.196(8) . ?
C2 C4 1.475(8) . ?
C3 H3 0.9800 . ?
C3 C4 1.531(7) . ?
C3 C5 1.586(9) . ?
C4 H4 0.9800 . ?
C4 C6 1.576(7) . ?
O4 C5 1.433(8) . ?
O4 C6 1.433(7) . ?
O5 C9 1.384(7) . ?
O5 C10 1.373(8) . ?
C5 H5 0.9800 . ?
C5 C7 1.497(10) . ?
O6 C9 1.187(7) . ?
C6 H6 0.9800 . ?
C6 C8 1.485(9) . ?
C7 H7 0.9300 . ?
C7 C8 1.304(11) . ?
O7 C10 1.172(7) . ?
C8 H8 0.9300 . ?
C9 C11 1.493(7) . ?
C10 C12 1.501(7) . ?
C11 H11 0.9800 . ?
C11 C12 1.544(7) . ?
C11 C13 1.565(7) . ?
C12 H12 0.9800 . ?
C12 C14 1.557(8) . ?
C13 H13 0.9800 . ?
C13 C15 1.514(7) . ?
C14 H14 0.9800 . ?
C14 C16 1.519(7) . ?
C15 H15 0.9300 . ?
C15 C16 1.314(8) . ?
C16 H16 0.9300 . ?

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 110.2(4) . . ?
O1 C1 C3 110.1(4) . . ?
O2 C1 O1 119.7(5) . . ?
O2 C1 C3 130.2(6) . . ?
C13 O8 C14 96.6(4) . . ?
O1 C2 C4 111.4(5) . . ?
O3 C2 O1 119.1(5) . . ?
O3 C2 C4 129.5(6) . . ?
C1 C3 H3 112.2 . . ?
C1 C3 C4 104.1(4) . . ?
C1 C3 C5 114.0(5) . . ?
C4 C3 H3 112.2 . . ?
C4 C3 C5 101.3(4) . . ?
C5 C3 H3 112.2 . . ?
C2 C4 C3 104.1(4) . . ?
C2 C4 H4 111.9 . . ?
C2 C4 C6 115.6(4) . . ?
C3 C4 H4 111.9 . . ?
C3 C4 C6 100.6(4) . . ?
C6 C4 H4 111.9 . . ?
C5 O4 C6 96.1(4) . . ?
C10 O5 C9 110.6(4) . . ?
C3 C5 H5 115.7 . . ?
O4 C5 C3 99.3(5) . . ?
O4 C5 H5 115.7 . . ?
O4 C5 C7 102.2(5) . . ?
C7 C5 C3 106.1(5) . . ?
C7 C5 H5 115.7 . . ?
C4 C6 H6 115.1 . . ?
O4 C6 C4 100.0(4) . . ?
O4 C6 H6 115.1 . . ?
O4 C6 C8 102.3(5) . . ?
C8 C6 C4 107.5(4) . . ?
C8 C6 H6 115.1 . . ?
C5 C7 H7 127.0 . . ?
C8 C7 C5 106.0(6) . . ?
C8 C7 H7 127.0 . . ?
C6 C8 H8 126.9 . . ?
C7 C8 C6 106.2(6) . . ?
C7 C8 H8 126.9 . . ?
O5 C9 C11 110.5(5) . . ?
O6 C9 O5 119.7(5) . . ?
O6 C9 C11 129.7(5) . . ?
O5 C10 C12 110.9(4) . . ?
O7 C10 O5 119.4(5) . . ?
O7 C10 C12 129.7(6) . . ?
C9 C11 H11 113.2 . . ?
C9 C11 C12 104.3(4) . . ?
C9 C11 C13 111.5(4) . . ?
C12 C11 H11 113.2 . . ?
C12 C11 C13 100.3(4) . . ?
C13 C11 H11 113.2 . . ?
C10 C12 C11 103.6(4) . . ?
C10 C12 H12 113.1 . . ?
C10 C12 C14 111.0(4) . . ?
C11 C12 H12 113.1 . . ?
C11 C12 C14 101.9(4) . . ?
C14 C12 H12 113.1 . . ?
O8 C13 C11 100.6(3) . . ?
O8 C13 H13 115.3 . . ?
O8 C13 C15 101.9(5) . . ?
C11 C13 H13 115.3 . . ?
C15 C13 C11 106.5(4) . . ?
C15 C13 H13 115.3 . . ?
O8 C14 C12 99.8(4) . . ?
O8 C14 H14 115.6 . . ?
O8 C14 C16 101.8(4) . . ?
C12 C14 H14 115.6 . . ?
C16 C14 C12 106.2(4) . . ?
C16 C14 H14 115.6 . . ?
C13 C15 H15 126.9 . . ?
C16 C15 C13 106.1(5) . . ?
C16 C15 H15 126.9 . . ?
C14 C16 H16 127.2 . . ?
C15 C16 C14 105.7(5) . . ?
C15 C16 H16 127.2 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_(EXO-1)(FURAN)
_database_code_depnum_ccdc_archive 'CCDC 2376894'
loop_
_audit_author_name
_audit_author_address
'Cameron B. Lennox'
;McGill University
Canada
;
_audit_update_record             
;
2024-10-30 deposited with the CCDC.	2026-05-12 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 H16 O9'
_chemical_formula_weight         400.33

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

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

_cell_length_a                   11.1990(16)
_cell_length_b                   5.4807(9)
_cell_length_c                   14.732(2)
_cell_angle_alpha                90
_cell_angle_beta                 104.639(15)
_cell_angle_gamma                90
_cell_volume                     874.9(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    1064
_cell_measurement_theta_min      4.4560
_cell_measurement_theta_max      75.2370

_exptl_crystal_description       rod
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.520
_exptl_crystal_F_000             416
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.060
_exptl_absorpt_coefficient_mu    1.039
_shelx_estimated_absorpt_T_min   0.681
_shelx_estimated_absorpt_T_max   0.940
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.86427
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.81a (Rigaku Oxford Diffraction, 2023)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      120(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Atlas'
_diffrn_measurement_method       'w\ scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            4108
_diffrn_reflns_av_unetI/netI     0.0635
_diffrn_reflns_av_R_equivalents  0.0604
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         4.458
_diffrn_reflns_theta_max         77.194
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.977
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.977
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.977
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             1805
_reflns_number_gt                1323
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_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)+(0.0495P)²+2.1941P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_extinction_coef       0.0036(8)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         1805
_refine_ls_number_parameters     155
_refine_ls_number_restraints     10
_refine_ls_R_factor_all          0.1017
_refine_ls_R_factor_gt           0.0765
_refine_ls_wR_factor_ref         0.1921
_refine_ls_wR_factor_gt          0.1757
_refine_ls_goodness_of_fit_ref   1.097
_refine_ls_restrained_S_all      1.095
_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 0.9483(10) 0.293(2) 0.5015(7) 0.067(3) Uani 0.5 1 d D . P A -1
C1 C 1.0599(11) 0.279(2) 0.4881(7) 0.046(3) Uani 0.5 1 d D . P A -1
H1 H 1.105808 0.136706 0.481816 0.055 Uiso 0.5 1 calc R U P A -1
C2 C 1.0915(19) 0.504(3) 0.4855(12) 0.046(7) Uani 0.5 1 d D U P A -1
H2 H 1.167177 0.560372 0.475178 0.055 Uiso 0.5 1 calc R U P A -1
C3 C 0.9975(12) 0.651(3) 0.5001(11) 0.048(3) Uani 0.5 1 d D U P A -1
H3 H 0.998899 0.824195 0.502251 0.057 Uiso 0.5 1 calc R U P A -1
C4 C 0.9075(15) 0.515(3) 0.5102(12) 0.053(9) Uani 0.5 1 d D . P A -1
H4 H 0.830892 0.563041 0.521239 0.064 Uiso 0.5 1 calc R U P A -1
O2 O 0.6743(3) 0.4155(6) 0.8068(2) 0.0451(9) Uani 1 1 d . . . B -1
O3 O 0.3742(2) 0.6368(5) 0.66124(18) 0.0273(6) Uani 1 1 d . . . B -1
O4 O 0.6072(3) 0.6859(6) 0.51536(19) 0.0356(7) Uani 1 1 d . . . B -1
O5 O 0.6434(2) 0.4995(5) 0.65437(19) 0.0292(7) Uani 1 1 d . . . B -1
C5 C 0.6332(3) 0.5517(8) 0.7440(3) 0.0312(9) Uani 1 1 d . . . B -1
C6 C 0.5630(3) 0.7852(7) 0.7441(3) 0.0266(8) Uani 1 1 d . . . B -1
H6 H 0.607987 0.906636 0.791063 0.032 Uiso 1 1 calc R U . B -1
C7 C 0.4290(3) 0.7279(7) 0.7538(3) 0.0260(8) Uani 1 1 d . . . B -1
H7 H 0.424020 0.617168 0.806630 0.031 Uiso 1 1 calc R U . B -1
C8 C 0.3659(4) 0.9736(8) 0.7522(3) 0.0308(9) Uani 1 1 d . . . B -1
H8 H 0.346795 1.054901 0.803661 0.037 Uiso 1 1 calc R U . B -1
C9 C 0.3431(3) 1.0514(7) 0.6644(3) 0.0281(8) Uani 1 1 d . . . B -1
H9 H 0.303988 1.199468 0.639634 0.034 Uiso 1 1 calc R U . B -1
C10 C 0.3924(3) 0.8544(7) 0.6121(3) 0.0266(8) Uani 1 1 d . . . B -1
H10 H 0.355521 0.851018 0.542759 0.032 Uiso 1 1 calc R U . B -1
C11 C 0.5371(3) 0.8769(7) 0.6426(3) 0.0256(8) Uani 1 1 d . . . B -1
H11 H 0.567547 1.046419 0.637259 0.031 Uiso 1 1 calc R U . B -1
C12 C 0.5964(3) 0.6888(7) 0.5938(3) 0.0260(8) Uani 1 1 d . . . B -1


_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 1.315(18) . ?
O1 C1 1.316(12) . ?
C1 C2 1.288(15) . ?
C1 H1 0.9500 . ?
C2 C3 1.38(2) . ?
C2 H2 0.9500 . ?
C3 C4 1.292(15) . ?
C3 H3 0.9500 . ?
C4 H4 0.9500 . ?
O2 C5 1.188(5) . ?
O3 C7 1.436(4) . ?
O3 C10 1.437(4) . ?
O4 C12 1.192(4) . ?
O5 C12 1.383(5) . ?
O5 C5 1.384(5) . ?
C5 C6 1.503(6) . ?
C6 C11 1.533(5) . ?
C6 C7 1.575(5) . ?
C6 H6 1.0000 . ?
C7 C8 1.517(5) . ?
C7 H7 1.0000 . ?
C8 C9 1.324(5) . ?
C8 H8 0.9500 . ?
C9 C10 1.510(5) . ?
C9 H9 0.9500 . ?
C10 C11 1.572(5) . ?
C10 H10 1.0000 . ?
C11 C12 1.504(5) . ?
C11 H11 1.0000 . ?

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 115.9(14) . . ?
C2 C1 O1 103.0(15) . . ?
C2 C1 H1 128.5 . . ?
O1 C1 H1 128.5 . . ?
C1 C2 C3 109.1(14) . . ?
C1 C2 H2 125.4 . . ?
C3 C2 H2 125.4 . . ?
C4 C3 C2 109.1(13) . . ?
C4 C3 H3 125.4 . . ?
C2 C3 H3 125.4 . . ?
C3 C4 O1 102.8(14) . . ?
C3 C4 H4 128.6 . . ?
O1 C4 H4 128.6 . . ?
C7 O3 C10 96.2(3) . . ?
C12 O5 C5 110.5(3) . . ?
O2 C5 O5 120.3(4) . . ?
O2 C5 C6 129.4(4) . . ?
O5 C5 C6 110.2(3) . . ?
C5 C6 C11 104.4(3) . . ?
C5 C6 C7 110.0(3) . . ?
C11 C6 C7 101.8(3) . . ?
C5 C6 H6 113.3 . . ?
C11 C6 H6 113.3 . . ?
C7 C6 H6 113.3 . . ?
O3 C7 C8 102.0(3) . . ?
O3 C7 C6 99.9(3) . . ?
C8 C7 C6 105.8(3) . . ?
O3 C7 H7 115.7 . . ?
C8 C7 H7 115.7 . . ?
C6 C7 H7 115.7 . . ?
C9 C8 C7 106.0(3) . . ?
C9 C8 H8 127.0 . . ?
C7 C8 H8 127.0 . . ?
C8 C9 C10 105.2(3) . . ?
C8 C9 H9 127.4 . . ?
C10 C9 H9 127.4 . . ?
O3 C10 C9 102.6(3) . . ?
O3 C10 C11 100.8(3) . . ?
C9 C10 C11 106.3(3) . . ?
O3 C10 H10 115.1 . . ?
C9 C10 H10 115.1 . . ?
C11 C10 H10 115.1 . . ?
C12 C11 C6 104.1(3) . . ?
C12 C11 C10 110.9(3) . . ?
C6 C11 C10 100.5(3) . . ?
C12 C11 H11 113.4 . . ?
C6 C11 H11 113.4 . . ?
C10 C11 H11 113.4 . . ?
O4 C12 O5 120.0(3) . . ?
O4 C12 C11 129.6(4) . . ?
O5 C12 C11 110.4(3) . . ?

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 O1 C1 C2 -1.7(13) . . . . ?
O1 C1 C2 C3 1.5(16) . . . . ?
C1 C2 C3 C4 -1(2) . . . . ?
C2 C3 C4 O1 -0.1(18) . . . . ?
C1 O1 C4 C3 1.2(15) . . . . ?
C12 O5 C5 O2 -176.3(4) . . . . ?
C12 O5 C5 C6 5.7(4) . . . . ?
O2 C5 C6 C11 179.4(4) . . . . ?
O5 C5 C6 C11 -2.9(4) . . . . ?
O2 C5 C6 C7 -72.1(5) . . . . ?
O5 C5 C6 C7 105.6(3) . . . . ?
C10 O3 C7 C8 48.7(3) . . . . ?
C10 O3 C7 C6 -60.0(3) . . . . ?
C5 C6 C7 O3 -73.9(4) . . . . ?
C11 C6 C7 O3 36.4(3) . . . . ?
C5 C6 C7 C8 -179.5(3) . . . . ?
C11 C6 C7 C8 -69.2(4) . . . . ?
O3 C7 C8 C9 -31.3(4) . . . . ?
C6 C7 C8 C9 72.7(4) . . . . ?
C7 C8 C9 C10 -0.2(4) . . . . ?
C7 O3 C10 C9 -49.2(3) . . . . ?
C7 O3 C10 C11 60.4(3) . . . . ?
C8 C9 C10 O3 31.7(4) . . . . ?
C8 C9 C10 C11 -73.7(4) . . . . ?
C5 C6 C11 C12 -0.7(4) . . . . ?
C7 C6 C11 C12 -115.2(3) . . . . ?
C5 C6 C11 C10 114.1(3) . . . . ?
C7 C6 C11 C10 -0.3(4) . . . . ?
O3 C10 C11 C12 73.6(3) . . . . ?
C9 C10 C11 C12 -179.6(3) . . . . ?
O3 C10 C11 C6 -36.0(3) . . . . ?
C9 C10 C11 C6 70.8(3) . . . . ?
C5 O5 C12 O4 173.4(3) . . . . ?
C5 O5 C12 C11 -6.2(4) . . . . ?
C6 C11 C12 O4 -175.4(4) . . . . ?
C10 C11 C12 O4 77.3(5) . . . . ?
C6 C11 C12 O5 4.1(4) . . . . ?
C10 C11 C12 O5 -103.1(3) . . . . ?

_refine_diff_density_max         0.297
_refine_diff_density_min         -0.345
_refine_diff_density_rms         0.077

####################################################################### 
# 
# 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_(endo-1)-200K
_database_code_depnum_ccdc_archive 'CCDC 2376891'
loop_
_audit_author_name
_audit_author_address
'Cameron Lennox'
;McGill University
Canada
;
_audit_update_record             
;
2025-02-18 deposited with the CCDC.	2026-05-12 downloaded from the CCDC.
;
_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        
'endo-7-oxabicyclo(2.2.1)-5-heptene-2,3-dicarboxylic anhydride'
_chemical_name_common            ?
_chemical_formula_moiety         'C8 H6 O4'
_chemical_formula_sum            'C8 H6 O4'
_chemical_properties_physical    moisture-sensitive
_exptl_crystal_recrystallization_method neat
_chemical_melting_point          348
_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_diffrn_ambient_temperature      200
_diffrn_ambient_pressure         1013
_chemical_formula_weight         166.13
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'

_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'
_chemical_absolute_configuration .
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'

_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.
;
_cell_length_a                   11.2298(4)
_cell_length_b                   5.6750(2)
_cell_length_c                   11.3656(4)
_cell_angle_alpha                90
_cell_angle_beta                 103.9030(10)
_cell_angle_gamma                90
_cell_volume                     703.10(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    200(2)
_cell_measurement_reflns_used    6183
_cell_measurement_theta_min      22.462
_cell_measurement_theta_max      144.272
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.569
_exptl_crystal_F_000             344
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.447
_exptl_crystal_size_mid          0.254
_exptl_crystal_size_min          0.182
_exptl_absorpt_coefficient_mu    1.103
_shelx_estimated_absorpt_T_min   0.638
_shelx_estimated_absorpt_T_max   0.824
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5781
_exptl_absorpt_correction_T_max  0.7536
_exptl_absorpt_process_details   'SADABS-2012/1, G. Sheldrick'
_exptl_absorpt_special_details   ?
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   'sealed x-ray tube'
_diffrn_source_type              'Bruker D8 Venture'
_diffrn_measurement_device_type  'Bruker PHOTON 100 CMOS'
_diffrn_measurement_method       'omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            5571
_diffrn_reflns_av_unetI/netI     0.0331
_diffrn_reflns_av_R_equivalents  0.0362
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         11.238
_diffrn_reflns_theta_max         72.243
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.947
_diffrn_measured_fraction_theta_full 0.945
_diffrn_reflns_Laue_measured_fraction_max 0.947
_diffrn_reflns_Laue_measured_fraction_full 0.945
_diffrn_reflns_point_group_measured_fraction_max 0.947
_diffrn_reflns_point_group_measured_fraction_full 0.945
_reflns_number_total             1304
_reflns_number_gt                1204
_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       'APEX 2, Bruker-AXS'
_computing_cell_refinement       'SAINT V8.35A, Bruker-AXS'
_computing_data_reduction        'SAINT V8.35A, Bruker-AXS'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_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)+(0.0274P)²+0.3026P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         1304
_refine_ls_number_parameters     109
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0413
_refine_ls_R_factor_gt           0.0384
_refine_ls_wR_factor_ref         0.0914
_refine_ls_wR_factor_gt          0.0892
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_restrained_S_all      1.054
_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 0.70569(8) 0.56694(17) 0.40056(8) 0.0326(3) Uani 1 1 d . . . . .
C1 C 0.64307(12) 0.3620(3) 0.35635(12) 0.0313(3) Uani 1 1 d . . . . .
O2 O 0.53782(10) 0.3400(2) 0.35642(11) 0.0481(3) Uani 1 1 d . . . . .
C2 C 0.82813(12) 0.5511(2) 0.39717(11) 0.0281(3) Uani 1 1 d . . . . .
O3 O 0.89560(9) 0.71316(18) 0.42971(9) 0.0377(3) Uani 1 1 d . . . . .
C3 C 0.72772(12) 0.1956(2) 0.31389(12) 0.0292(3) Uani 1 1 d . . . . .
H3 H 0.730953 0.041541 0.353491 0.035 Uiso 1 1 calc R U . . .
C4 C 0.85203(11) 0.3185(2) 0.34508(11) 0.0275(3) Uani 1 1 d . . . . .
H4 H 0.914239 0.226368 0.401809 0.033 Uiso 1 1 calc R U . . .
O4 O 0.82777(9) 0.12148(17) 0.16354(9) 0.0358(3) Uani 1 1 d . . . . .
C6 C 0.88064(12) 0.3385(2) 0.21626(13) 0.0310(3) Uani 1 1 d . . . . .
H6 H 0.967207 0.361801 0.216677 0.037 Uiso 1 1 calc R U . . .
C5 C 0.70453(12) 0.1714(3) 0.17245(13) 0.0343(4) Uani 1 1 d . . . . .
H5 H 0.642608 0.054849 0.134912 0.041 Uiso 1 1 calc R U . . .
C8 C 0.79370(14) 0.5189(3) 0.14643(12) 0.0357(4) Uani 1 1 d . . . . .
H8 H 0.812544 0.670718 0.125993 0.043 Uiso 1 1 calc R U . . .
C7 C 0.68499(14) 0.4165(3) 0.12019(12) 0.0390(4) Uani 1 1 d . . . . .
H7 H 0.611214 0.482267 0.077983 0.047 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 C2 1.3876(16) . ?
O1 C1 1.3890(17) . ?
C1 O2 1.1887(17) . ?
C1 C3 1.4997(19) . ?
C2 O3 1.1925(17) . ?
C2 C4 1.4973(18) . ?
C3 C4 1.5241(18) . ?
C3 C5 1.5715(19) . ?
C3 H3 0.9800 . ?
C4 C6 1.5767(18) . ?
C4 H4 0.9800 . ?
O4 C6 1.4343(16) . ?
O4 C5 1.4398(17) . ?
C6 C8 1.503(2) . ?
C6 H6 0.9800 . ?
C5 C7 1.508(2) . ?
C5 H5 0.9800 . ?
C8 C7 1.320(2) . ?
C8 H8 0.9300 . ?
C7 H7 0.9300 . ?

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 110.77(10) . . ?
O2 C1 O1 120.32(13) . . ?
O2 C1 C3 129.88(14) . . ?
O1 C1 C3 109.80(11) . . ?
O3 C2 O1 120.10(12) . . ?
O3 C2 C4 129.92(12) . . ?
O1 C2 C4 109.94(11) . . ?
C1 C3 C4 104.65(11) . . ?
C1 C3 C5 114.97(11) . . ?
C4 C3 C5 101.26(10) . . ?
C1 C3 H3 111.7 . . ?
C4 C3 H3 111.7 . . ?
C5 C3 H3 111.7 . . ?
C2 C4 C3 104.72(10) . . ?
C2 C4 C6 113.55(11) . . ?
C3 C4 C6 101.34(10) . . ?
C2 C4 H4 112.2 . . ?
C3 C4 H4 112.2 . . ?
C6 C4 H4 112.2 . . ?
C6 O4 C5 96.32(9) . . ?
O4 C6 C8 102.30(11) . . ?
O4 C6 C4 99.77(10) . . ?
C8 C6 C4 106.75(10) . . ?
O4 C6 H6 115.4 . . ?
C8 C6 H6 115.4 . . ?
C4 C6 H6 115.4 . . ?
O4 C5 C7 101.84(11) . . ?
O4 C5 C3 99.40(10) . . ?
C7 C5 C3 107.15(11) . . ?
O4 C5 H5 115.5 . . ?
C7 C5 H5 115.5 . . ?
C3 C5 H5 115.5 . . ?
C7 C8 C6 105.53(13) . . ?
C7 C8 H8 127.2 . . ?
C6 C8 H8 127.2 . . ?
C8 C7 C5 106.14(12) . . ?
C8 C7 H7 126.9 . . ?
C5 C7 H7 126.9 . . ?

_refine_diff_density_max         0.232
_refine_diff_density_min         -0.154
_refine_diff_density_rms         0.033
####################################################################### 
# 
# 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_(endo-1)(exo-1)_200K
_database_code_depnum_ccdc_archive 'CCDC 2376887'
loop_
_audit_author_name
_audit_author_address
'Cameron Lennox'
;McGill University
Canada
;
_audit_update_record             
;
2024-08-11 deposited with the CCDC.	2026-05-12 downloaded from the CCDC.
;
_audit_creation_date             2024-05-30
_audit_creation_method           
;
Olex2 1.5
(compiled 2024.01.12 svn.r2f8d729c for OlexSys, GUI svn.r6928)
;
_shelx_SHELXL_version_number     2018/3
# end Validation Reply Form
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '2(C8 H6 O4)'
_chemical_formula_sum            'C16 H12 O8'
_chemical_formula_weight         332.26
_chemical_absolute_configuration ?
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C12 O6'
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           7
_space_group_name_H-M_alt        'P 1 n 1'
_space_group_name_Hall           'P -2yac'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'x+1/2, -y, z+1/2'

_cell_length_a                   11.9141(14)
_cell_length_b                   5.3741(4)
_cell_length_c                   11.9214(14)
_cell_angle_alpha                90
_cell_angle_beta                 110.400(13)
_cell_angle_gamma                90
_cell_volume                     715.43(14)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    5065
_cell_measurement_temperature    199.99(10)
_cell_measurement_theta_max      76.5500
_cell_measurement_theta_min      4.4560
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    1.084
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.91874
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.43.116a (Rigaku Oxford Diffraction, 2024)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.542
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             344
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.123
_exptl_crystal_size_min          0.109
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0555
_diffrn_reflns_av_unetI/netI     0.0376
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.984
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            12020
_diffrn_reflns_point_group_measured_fraction_full 0.954
_diffrn_reflns_point_group_measured_fraction_max 0.921
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.834
_diffrn_reflns_theta_min         3.956
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      199.99(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.1768
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -52.00 -23.00   1.00    1.00    --  -39.96  37.00-134.00   29
  2  ω    -66.00 -27.00   1.00    1.00    --  -39.96 -37.00  70.00   39
  3  ω    -20.00  36.00   1.00    1.00    --  -39.96  37.00-134.00   56
  4  ω   -115.00 -67.00   1.00    1.00    --  -39.96 -37.00  70.00   48
  5  ω    108.00 133.00   1.00    1.10    --  113.00  37.00-134.00   25
  6  ω     66.00 109.00   1.00    1.10    --  113.00 -37.00  70.00   43
  7  ω   -112.00 -82.00   1.00    1.00    --  -39.96 -57.00-150.00   30
  8  ω    -68.00 -17.00   1.00    1.00    --  -39.96 -57.00-150.00   51
  9  ω      8.00  81.00   1.00    1.00    --   39.96 -99.00 -30.00   73
 10  ω     29.00  78.00   1.00    1.00    --   39.96-125.00 120.00   49
 11  ω     29.00  89.00   1.00    1.00    --   39.96-125.00-120.00   60
 12  ω    -33.00  16.00   1.00    1.00    --   39.96 -37.00  70.00   49
 13  ω     14.00  43.00   1.00    1.00    --   39.96  37.00-134.00   29
 14  ω     82.00 109.00   1.00    1.00    --   39.96  37.00-134.00   27
 15  ω      6.00  31.00   1.00    1.00    --   39.96  77.00 -95.93   25
 16  ω     13.00  38.00   1.00    1.00    --   48.00  82.00 -49.18   25
 17  ω     14.00  39.00   1.00    1.00    --   48.00  81.00  -9.30   25
 18  ω     14.00  39.00   1.00    1.00    --   48.00  79.00 126.66   25
 19  ω     14.00  39.00   1.00    1.00    --   48.00  79.00 -84.07   25
 20  ω     14.00  39.00   1.00    1.00    --   48.00  81.00 176.67   25
 21  ω     13.00  38.00   1.00    1.00    --   48.00  81.00  47.63   25
 22  ω     29.00 131.00   1.00    1.00    --   56.00  70.00 -48.16  102
 23  ω     30.00  67.00   1.00    1.00    --   60.00  66.00  67.39   37
 24  ω     32.00  59.00   1.00    1.00    --   60.00  67.00 142.38   27
 25  ω     39.00  67.00   1.00    1.00    --   68.00  71.00  94.87   28
 26  ω    111.00 142.00   1.00    1.00    --   68.00  71.00  94.87   31
 27  ω     38.00  65.00   1.00    1.00    --   68.00  71.00-159.61   27
 28  ω    114.00 147.00   1.00    1.00    --   72.00  71.00  56.55   33
 29  ω     40.00  72.00   1.00    1.00    --   72.00  70.00 170.89   32
 30  ω     40.00  92.00   1.00    1.00    --   72.00  70.00 -14.83   52
 31  ω     40.00  67.00   1.00    1.00    --   72.00  69.00-120.61   27
 32  ω     40.00 145.00   1.00    1.00    --   72.00  71.00-102.88  105
 33  ω     41.00 105.00   1.00    1.00    --   72.00  71.00  56.55   64
 34  ω     78.00 148.00   1.00    1.00    --   72.00  70.00 170.89   70
 35  ω     84.00 109.00   1.00    1.10    --  113.00  61.00  60.00   25
 36  ω    124.00 174.00   1.00    1.10    --  113.00  61.00-120.00   50
 37  ω     39.00 109.00   1.00    1.10    --  113.00-111.00 120.00   70
 38  ω     86.00 111.00   1.00    1.10    --  113.00  45.00 120.00   25
 39  ω     83.00 117.00   1.00    1.10    --  113.00  61.00-120.00   34
 40  ω     83.00 175.00   1.00    1.10    --  113.00  61.00 -60.00   92
 41  ω     64.00 147.00   1.00    1.10    --  113.00 -77.00  90.00   83
 42  ω     91.00 118.00   1.00    1.10    --  113.00  45.00  90.00   27
 43  ω     86.00 112.00   1.00    1.10    --  113.00  45.00-120.00   26
 44  ω     39.00 107.00   1.00    1.10    --  113.00-111.00 -30.00   68
 45  ω     43.00 108.00   1.00    1.10    --  113.00-111.00 -90.00   65
 46  ω    132.00 159.00   1.00    1.10    --  113.00  61.00 150.00   27
 47  ω    115.00 141.00   1.00    1.10    --  113.00 -61.00 150.00   26
 48  ω    131.00 166.00   1.00    1.10    --  113.00  61.00  90.00   35
 49  ω     84.00 119.00   1.00    1.10    --  113.00  61.00 150.00   35
 50  ω     85.00 177.00   1.00    1.10    --  113.00  61.00 120.00   92
 51  ω    125.00 176.00   1.00    1.10    --  113.00  61.00  30.00   51
 52  ω     83.00 162.00   1.00    1.10    --  113.00  61.00-180.00   79
 53  ω     83.00 114.00   1.00    1.10    --  113.00  61.00  30.00   31
 54  ω     83.00 167.00   1.00    1.10    --  113.00  61.00   0.00   84
 55  ω     83.00 127.00   1.00    1.10    --  113.00  61.00  90.00   44
 56  ω    116.00 174.00   1.00    1.10    --  113.00  61.00 -30.00   58
 57  ω     84.00 109.00   1.00    1.10    --  113.00  61.00 -30.00   25
 58  ω    130.00 172.00   1.00    1.10    --  113.00  61.00-150.00   42
 59  ω     83.00 109.00   1.00    1.10    --  113.00  61.00-150.00   26
 60  ω     42.00 109.00   1.00    1.10    --  113.00-111.00  30.00   67
 61  ω     86.00 173.00   1.00    1.10    --  113.00  61.00 -90.00   87
 62  ω    129.00 167.00   1.00    1.10    --  113.00  61.00  60.00   38
 63  ω     33.00  82.00   1.00    1.10    --  113.00 -94.00  60.00   49
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0553819000
_diffrn_orient_matrix_UB_12      0.1054295000
_diffrn_orient_matrix_UB_13      0.0891706000
_diffrn_orient_matrix_UB_21      0.0345521000
_diffrn_orient_matrix_UB_22      0.2652497000
_diffrn_orient_matrix_UB_23      -0.0250415000
_diffrn_orient_matrix_UB_31      -0.1214861000
_diffrn_orient_matrix_UB_32      0.0270814000
_diffrn_orient_matrix_UB_33      -0.1020300000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.868
_reflns_Friedel_fraction_full    0.908
_reflns_Friedel_fraction_max     0.858
_reflns_number_gt                2587
_reflns_number_total             2824
_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. Completness statistics refer to single and
 composite reflections containing twin component 1 only.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.43.116a (Rigaku OD, 2024)'
_computing_data_collection       
'CrysAlisPro system (CCD 43.116a 64-bit (release 22-03-2024))'
_computing_data_reduction        'CrysAlisPro 1.171.43.116a (Rigaku OD, 2024)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    ?
_refine_diff_density_max         0.202
_refine_diff_density_min         -0.211
_refine_diff_density_rms         0.044
_refine_ls_abs_structure_details 
;
 Flack x determined using 1057 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.4(2)
_refine_ls_extinction_coef       0.0085(12)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     219
_refine_ls_number_reflns         2824
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0525
_refine_ls_R_factor_gt           0.0460
_refine_ls_restrained_S_all      1.056
_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)+(0.0491P)²+0.4179P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1118
_refine_ls_wR_factor_ref         0.1208
_refine_special_details          
;
 Refined as a 2-component twin.
;
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 0.57984
 0.42016
2.a Ternary CH refined with riding coordinates:
 C11(H11), C12(H12), C13(H13), C14(H14), C3(H3), C4(H4), C5(H5), C6(H6)
2.b Aromatic/amide H refined with riding coordinates:
 C15(H15), C16(H16), C7(H7), C8(H8)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_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 0.4996(5) 0.0886(8) 0.6493(4) 0.0411(10) Uani 1 1 d . . . . .
C9 C 0.3919(6) 0.5981(12) 0.1693(6) 0.0371(14) Uani 1 1 d . . . . .
C10 C 0.4425(6) 0.5872(13) 0.3696(6) 0.0417(16) Uani 1 1 d . . . . .
C11 C 0.4532(6) 0.8418(11) 0.2105(6) 0.0353(14) Uani 1 1 d . . . . .
H11 H 0.402927 0.988237 0.171486 0.042 Uiso 1 1 calc R U . . .
C12 C 0.4848(6) 0.8375(11) 0.3462(6) 0.0375(14) Uani 1 1 d . . . . .
H12 H 0.450002 0.979120 0.377661 0.045 Uiso 1 1 calc R U . . .
C13 C 0.5804(6) 0.8440(12) 0.1983(6) 0.0389(15) Uani 1 1 d . . . . .
H13 H 0.583166 0.792294 0.118755 0.047 Uiso 1 1 calc R U . . .
C14 C 0.6257(7) 0.8399(12) 0.3898(6) 0.0399(15) Uani 1 1 d . . . . .
H14 H 0.667960 0.783651 0.474003 0.048 Uiso 1 1 calc R U . . .
C15 C 0.6313(6) 1.1012(12) 0.2422(7) 0.0415(16) Uani 1 1 d . . . . .
H15 H 0.640394 1.236973 0.195100 0.050 Uiso 1 1 calc R U . . .
C16 C 0.6596(7) 1.0951(12) 0.3590(7) 0.0433(17) Uani 1 1 d . . . . .
H16 H 0.694772 1.225841 0.413562 0.052 Uiso 1 1 calc R U . . .
O8 O 0.6455(4) 0.6896(8) 0.2977(4) 0.0428(11) Uani 1 1 d . . . . .
O7 O 0.4493(6) 0.4926(11) 0.4625(5) 0.0622(15) Uani 1 1 d . . . . .
O6 O 0.3499(5) 0.5138(11) 0.0710(5) 0.0529(13) Uani 1 1 d . . . . .
O5 O 0.3912(5) 0.4549(8) 0.2659(4) 0.0438(11) Uani 1 1 d . . . . .
C2 C 0.6037(6) 0.2244(13) 0.6983(6) 0.0437(16) Uani 1 1 d . . . . .
C3 C 0.4394(6) 0.4685(13) 0.7122(6) 0.0376(14) Uani 1 1 d . . . . .
H3 H 0.399405 0.612144 0.660290 0.045 Uiso 1 1 calc R U . . .
C4 C 0.5769(6) 0.4710(12) 0.7425(6) 0.0388(14) Uani 1 1 d . . . . .
H4 H 0.602947 0.613277 0.703359 0.047 Uiso 1 1 calc R U . . .
C5 C 0.4314(6) 0.4878(13) 0.8401(6) 0.0403(16) Uani 1 1 d . . . . .
H5 H 0.352024 0.541869 0.842608 0.048 Uiso 1 1 calc R U . . .
C6 C 0.6221(7) 0.4989(14) 0.8814(7) 0.0461(18) Uani 1 1 d . . . . .
H6 H 0.705649 0.563102 0.918925 0.055 Uiso 1 1 calc R U . . .
C7 C 0.4790(8) 0.2486(13) 0.9038(7) 0.0484(18) Uani 1 1 d . . . . .
H7 H 0.434052 0.118333 0.921790 0.058 Uiso 1 1 calc R U . . .
C8 C 0.5970(8) 0.2563(15) 0.9298(7) 0.053(2) Uani 1 1 d . . . . .
H8 H 0.653698 0.133132 0.970626 0.064 Uiso 1 1 calc R U . . .
O4 O 0.5290(5) 0.6586(8) 0.8932(5) 0.0486(12) Uani 1 1 d . . . . .
C1 C 0.4010(6) 0.2238(12) 0.6503(6) 0.0407(15) Uani 1 1 d . . . . .
O3 O 0.6977(5) 0.1340(9) 0.7037(6) 0.0607(15) Uani 1 1 d . . . . .
O2 O 0.3021(5) 0.1384(10) 0.6068(5) 0.0535(14) 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 1.381(9) . ?
O1 C1 1.385(8) . ?
C9 C11 1.497(8) . ?
C9 O6 1.191(9) . ?
C9 O5 1.388(8) . ?
C10 C12 1.497(8) . ?
C10 O7 1.194(8) . ?
C10 O5 1.371(9) . ?
C11 H11 1.0000 . ?
C11 C12 1.528(9) . ?
C11 C13 1.573(9) . ?
C12 H12 1.0000 . ?
C12 C14 1.575(10) . ?
C13 H13 1.0000 . ?
C13 C15 1.527(9) . ?
C13 O8 1.433(8) . ?
C14 H14 1.0000 . ?
C14 C16 1.511(9) . ?
C14 O8 1.447(8) . ?
C15 H15 0.9500 . ?
C15 C16 1.313(10) . ?
C16 H16 0.9500 . ?
C2 C4 1.501(9) . ?
C2 O3 1.201(9) . ?
C3 H3 1.0000 . ?
C3 C4 1.549(10) . ?
C3 C5 1.564(9) . ?
C3 C1 1.499(9) . ?
C4 H4 1.0000 . ?
C4 C6 1.560(10) . ?
C5 H5 1.0000 . ?
C5 C7 1.500(9) . ?
C5 O4 1.443(8) . ?
C6 H6 1.0000 . ?
C6 C8 1.497(11) . ?
C6 O4 1.447(9) . ?
C7 H7 0.9500 . ?
C7 C8 1.331(12) . ?
C8 H8 0.9500 . ?
C1 O2 1.201(8) . ?

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 111.0(5) . . ?
O6 C9 C11 130.2(6) . . ?
O6 C9 O5 118.9(6) . . ?
O5 C9 C11 110.8(5) . . ?
O7 C10 C12 129.5(7) . . ?
O7 C10 O5 118.7(6) . . ?
O5 C10 C12 111.8(5) . . ?
C9 C11 H11 113.0 . . ?
C9 C11 C12 104.3(5) . . ?
C9 C11 C13 110.6(5) . . ?
C12 C11 H11 113.0 . . ?
C12 C11 C13 102.0(6) . . ?
C13 C11 H11 113.0 . . ?
C10 C12 C11 103.7(5) . . ?
C10 C12 H12 113.8 . . ?
C10 C12 C14 109.6(5) . . ?
C11 C12 H12 113.8 . . ?
C11 C12 C14 101.0(6) . . ?
C14 C12 H12 113.8 . . ?
C11 C13 H13 115.9 . . ?
C15 C13 C11 104.8(5) . . ?
C15 C13 H13 115.9 . . ?
O8 C13 C11 100.4(5) . . ?
O8 C13 H13 115.9 . . ?
O8 C13 C15 101.8(5) . . ?
C12 C14 H14 115.8 . . ?
C16 C14 C12 105.8(5) . . ?
C16 C14 H14 115.8 . . ?
O8 C14 C12 100.5(5) . . ?
O8 C14 H14 115.8 . . ?
O8 C14 C16 101.2(6) . . ?
C13 C15 H15 127.3 . . ?
C16 C15 C13 105.4(6) . . ?
C16 C15 H15 127.3 . . ?
C14 C16 H16 126.6 . . ?
C15 C16 C14 106.8(6) . . ?
C15 C16 H16 126.6 . . ?
C13 O8 C14 96.9(5) . . ?
C10 O5 C9 109.3(5) . . ?
O1 C2 C4 110.2(6) . . ?
O3 C2 O1 119.4(6) . . ?
O3 C2 C4 130.3(7) . . ?
C4 C3 H3 112.0 . . ?
C4 C3 C5 101.0(5) . . ?
C5 C3 H3 112.0 . . ?
C1 C3 H3 112.0 . . ?
C1 C3 C4 103.8(5) . . ?
C1 C3 C5 115.2(6) . . ?
C2 C4 C3 104.4(5) . . ?
C2 C4 H4 111.9 . . ?
C2 C4 C6 114.9(6) . . ?
C3 C4 H4 111.9 . . ?
C3 C4 C6 101.2(5) . . ?
C6 C4 H4 111.9 . . ?
C3 C5 H5 115.3 . . ?
C7 C5 C3 107.2(5) . . ?
C7 C5 H5 115.3 . . ?
O4 C5 C3 99.0(6) . . ?
O4 C5 H5 115.3 . . ?
O4 C5 C7 102.7(6) . . ?
C4 C6 H6 115.4 . . ?
C8 C6 C4 106.5(6) . . ?
C8 C6 H6 115.4 . . ?
O4 C6 C4 99.7(5) . . ?
O4 C6 H6 115.4 . . ?
O4 C6 C8 102.5(6) . . ?
C5 C7 H7 127.1 . . ?
C8 C7 C5 105.8(7) . . ?
C8 C7 H7 127.1 . . ?
C6 C8 H8 127.1 . . ?
C7 C8 C6 105.9(7) . . ?
C7 C8 H8 127.1 . . ?
C5 O4 C6 96.2(5) . . ?
O1 C1 C3 110.5(5) . . ?
O2 C1 O1 120.2(6) . . ?
O2 C1 C3 129.3(6) . . ?

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 C2 C4 C3 -0.5(8) . . . . ?
O1 C2 C4 C6 109.3(7) . . . . ?
C9 C11 C12 C10 2.1(7) . . . . ?
C9 C11 C12 C14 115.5(5) . . . . ?
C9 C11 C13 C15 179.6(6) . . . . ?
C9 C11 C13 O8 -75.1(6) . . . . ?
C10 C12 C14 C16 178.2(6) . . . . ?
C10 C12 C14 O8 73.3(6) . . . . ?
C11 C9 O5 C10 2.8(7) . . . . ?
C11 C12 C14 C16 69.2(6) . . . . ?
C11 C12 C14 O8 -35.7(5) . . . . ?
C11 C13 C15 C16 73.5(6) . . . . ?
C11 C13 O8 C14 -58.9(5) . . . . ?
C12 C10 O5 C9 -1.3(7) . . . . ?
C12 C11 C13 C15 -70.0(6) . . . . ?
C12 C11 C13 O8 35.4(5) . . . . ?
C12 C14 C16 C15 -72.4(7) . . . . ?
C12 C14 O8 C13 59.4(5) . . . . ?
C13 C11 C12 C10 -113.1(5) . . . . ?
C13 C11 C12 C14 0.4(5) . . . . ?
C13 C15 C16 C14 -1.0(7) . . . . ?
C15 C13 O8 C14 48.8(6) . . . . ?
C16 C14 O8 C13 -49.2(6) . . . . ?
O8 C13 C15 C16 -30.7(7) . . . . ?
O8 C14 C16 C15 32.0(7) . . . . ?
O7 C10 C12 C11 178.2(7) . . . . ?
O7 C10 C12 C14 71.0(9) . . . . ?
O7 C10 O5 C9 179.8(6) . . . . ?
O6 C9 C11 C12 179.5(8) . . . . ?
O6 C9 C11 C13 -71.5(10) . . . . ?
O6 C9 O5 C10 -179.4(7) . . . . ?
O5 C9 C11 C12 -3.0(7) . . . . ?
O5 C9 C11 C13 106.0(6) . . . . ?
O5 C10 C12 C11 -0.6(7) . . . . ?
O5 C10 C12 C14 -107.7(6) . . . . ?
C2 O1 C1 C3 -3.9(7) . . . . ?
C2 O1 C1 O2 177.1(6) . . . . ?
C2 C4 C6 C8 -40.9(8) . . . . ?
C2 C4 C6 O4 -147.1(6) . . . . ?
C3 C4 C6 C8 70.8(7) . . . . ?
C3 C4 C6 O4 -35.4(6) . . . . ?
C3 C5 C7 C8 72.9(7) . . . . ?
C3 C5 O4 C6 -62.1(6) . . . . ?
C4 C3 C5 C7 -68.1(7) . . . . ?
C4 C3 C5 O4 38.2(6) . . . . ?
C4 C3 C1 O1 3.4(7) . . . . ?
C4 C3 C1 O2 -177.7(7) . . . . ?
C4 C6 C8 C7 -72.7(7) . . . . ?
C4 C6 O4 C5 61.2(6) . . . . ?
C5 C3 C4 C2 118.0(6) . . . . ?
C5 C3 C4 C6 -1.6(6) . . . . ?
C5 C3 C1 O1 -106.0(6) . . . . ?
C5 C3 C1 O2 72.8(9) . . . . ?
C5 C7 C8 C6 -0.4(8) . . . . ?
C7 C5 O4 C6 48.0(7) . . . . ?
C8 C6 O4 C5 -48.2(7) . . . . ?
O4 C5 C7 C8 -30.8(8) . . . . ?
O4 C6 C8 C7 31.4(8) . . . . ?
C1 O1 C2 C4 2.7(7) . . . . ?
C1 O1 C2 O3 -179.7(7) . . . . ?
C1 C3 C4 C2 -1.7(7) . . . . ?
C1 C3 C4 C6 -121.2(6) . . . . ?
C1 C3 C5 C7 42.9(8) . . . . ?
C1 C3 C5 O4 149.3(5) . . . . ?
O3 C2 C4 C3 -177.7(8) . . . . ?
O3 C2 C4 C6 -67.9(10) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.199
_oxdiff_exptl_absorpt_empirical_full_min 0.837
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 0.57984
2 0.42016

# start Validation Reply Form
_vrf_PLAT340_cocrystal_200_200524_autored 
;
PROBLEM: Low Bond Precision on  C-C Bonds ...............    0.01038 Ang.  
RESPONSE: This is related to crystal twinning.
;
