# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2022

####################################################################### 
# 
# 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_ml_art
_database_code_depnum_ccdc_archive 'CCDC 2115273'
loop_
_audit_author_name
_audit_author_address
'Colin Seaton' 'University of Bradford'
_audit_update_record             
;
2021-10-12 deposited with the CCDC.	2021-12-23 downloaded from the CCDC.
;
_audit_creation_date             2019-10-28
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3510 for OlexSys, GUI svn.r5506)
;
_shelxl_version_number           2013-4
_chemical_name_common            
;
artesiminin hemikis(acetylenedicarboxylic acid)
;
_chemical_name_systematic        
'Octahydro-3,6,9-trimethyl-3,12-epoxy-12H-pyrano(4,3-j)-1,2-benzodioxepin-10(3H)-one hemikis(but-2-ynedioic acid)'
_chemical_formula_moiety         'C15 H22 O5, 0.5(C4 H2 O4)'
_chemical_formula_sum            'C17 H23 O7'
_chemical_formula_weight         339.35
_chemical_absolute_configuration rm
_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 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           18
_space_group_name_H-M_alt        'P 21 21 2'
_space_group_name_Hall           'P 2 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z'
'-x+1/2, y+1/2, -z'
'x+1/2, -y+1/2, -z'

_cell_length_a                   10.5089(4)
_cell_length_b                   24.0830(11)
_cell_length_c                   6.4952(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1643.84(12)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    7627
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      33.39
_cell_measurement_theta_min      2.54
_shelx_estimated_absorpt_T_max   0.979
_shelx_estimated_absorpt_T_min   0.929
_exptl_absorpt_coefficient_mu    0.106
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.371
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             724
_exptl_crystal_size_max          0.7
_exptl_crystal_size_mid          0.49
_exptl_crystal_size_min          0.2
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0240
_diffrn_reflns_av_unetI/netI     0.0254
_diffrn_reflns_Laue_measured_fraction_full 0.985
_diffrn_reflns_Laue_measured_fraction_max 0.761
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       37
_diffrn_reflns_limit_k_min       -37
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            17651
_diffrn_reflns_point_group_measured_fraction_full 0.984
_diffrn_reflns_point_group_measured_fraction_max 0.721
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         36.253
_diffrn_reflns_theta_min         2.114
_diffrn_ambient_temperature      149.99
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.985
_diffrn_measured_fraction_theta_max 0.761
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.681
_reflns_Friedel_fraction_full    0.982
_reflns_Friedel_fraction_max     0.669
_reflns_number_gt                5191
_reflns_number_total             5737
_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       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.333
_refine_diff_density_min         -0.172
_refine_diff_density_rms         0.045
_refine_ls_abs_structure_details 
;
 Flack x determined using 2017 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   0.2(2)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     309
_refine_ls_number_reflns         5737
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0416
_refine_ls_R_factor_gt           0.0353
_refine_ls_restrained_S_all      1.039
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0603P)²+0.0505P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0884
_refine_ls_wR_factor_ref         0.0922
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
;
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O2A O 0.34887(9) 0.37278(4) 0.95831(14) 0.01900(18) Uani 1 1 d . . . . .
O3A O 0.17733(10) 0.31529(3) 0.97836(14) 0.01744(18) Uani 1 1 d . . . . .
O5A O 0.31278(11) 0.28467(4) 0.61430(15) 0.0223(2) Uani 1 1 d . . . . .
O4A O 0.31825(11) 0.25663(4) 0.81556(16) 0.0245(2) Uani 1 1 d . . . . .
O2B O 0.73330(11) 0.48222(5) 0.9702(2) 0.0289(2) Uani 1 1 d . . . . .
O1B O 0.83533(12) 0.40682(4) 0.8517(2) 0.0310(2) Uani 1 1 d . . . . .
O1A O 0.52541(12) 0.41979(5) 0.96369(18) 0.0322(3) Uani 1 1 d . . . . .
C1B C 0.83420(13) 0.45425(5) 0.9090(2) 0.0196(2) Uani 1 1 d . . . . .
C4A C 0.33975(12) 0.37846(5) 0.51803(18) 0.0166(2) Uani 1 1 d . . . . .
C1A C 0.44992(13) 0.39422(6) 0.8597(2) 0.0197(2) Uani 1 1 d . . . . .
C15A C 0.27740(14) 0.43527(5) 0.4839(2) 0.0205(3) Uani 1 1 d . . . . .
C2B C 0.95051(14) 0.48782(5) 0.9142(2) 0.0205(2) Uani 1 1 d . . . . .
C7A C 0.19525(14) 0.25935(5) 0.9032(2) 0.0213(3) Uani 1 1 d . . . . .
C5A C 0.24992(12) 0.33846(5) 0.62988(18) 0.0146(2) Uani 1 1 d . . . . .
C6A C 0.23211(12) 0.35562(5) 0.85407(17) 0.0137(2) Uani 1 1 d . . . . .
C14A C 0.15057(15) 0.42912(6) 0.3711(2) 0.0220(3) Uani 1 1 d . . . . .
C2A C 0.46683(13) 0.38072(6) 0.6339(2) 0.0195(2) Uani 1 1 d . . . . .
C12A C 0.05822(13) 0.38986(5) 0.4803(2) 0.0204(2) Uani 1 1 d . . . . .
C11A C 0.12020(13) 0.33281(5) 0.5220(2) 0.0184(2) Uani 1 1 d . . . . .
C10A C 0.02915(15) 0.29459(6) 0.6417(2) 0.0240(3) Uani 1 1 d . . . . .
C9A C 0.08965(16) 0.24446(6) 0.7486(3) 0.0268(3) Uani 1 1 d . . . . .
C3A C 0.56713(16) 0.41734(8) 0.5321(3) 0.0327(4) Uani 1 1 d . . . . .
C13A C -0.06427(16) 0.38393(8) 0.3545(3) 0.0323(3) Uani 1 1 d . . . . .
C8A C 0.19963(19) 0.22209(6) 1.0912(3) 0.0309(3) Uani 1 1 d . . . . .
H15A H 0.3383(18) 0.4609(8) 0.405(3) 0.027(5) Uiso 1 1 d . . . . .
H14A H 0.169(2) 0.4149(9) 0.231(3) 0.035(5) Uiso 1 1 d . . . . .
H11A H 0.1408(19) 0.3155(8) 0.390(3) 0.024(5) Uiso 1 1 d . . . . .
H14B H 0.110(2) 0.4662(9) 0.360(4) 0.033(5) Uiso 1 1 d . . . . .
H15B H 0.2675(19) 0.4529(8) 0.613(3) 0.026(5) Uiso 1 1 d . . . . .
H4A H 0.3571(19) 0.3626(8) 0.377(3) 0.027(5) Uiso 1 1 d . . . . .
H3AA H 0.651(2) 0.4086(10) 0.589(4) 0.041(6) Uiso 1 1 d . . . . .
H12A H 0.0338(17) 0.4038(7) 0.615(3) 0.015(4) Uiso 1 1 d . . . . .
H2B H 0.665(2) 0.4588(11) 0.965(4) 0.045(6) Uiso 1 1 d . . . . .
H13A H -0.104(2) 0.4214(11) 0.329(4) 0.044(6) Uiso 1 1 d . . . . .
H6A H 0.1768(17) 0.3880(7) 0.865(3) 0.016(4) Uiso 1 1 d . . . . .
H2A H 0.500(2) 0.3435(9) 0.633(3) 0.031(5) Uiso 1 1 d . . . . .
H8AA H 0.209(2) 0.1845(9) 1.050(4) 0.036(6) Uiso 1 1 d . . . . .
H9AA H 0.1266(19) 0.2194(8) 0.648(3) 0.024(5) Uiso 1 1 d . . . . .
H10A H -0.0151(19) 0.3159(9) 0.747(3) 0.029(5) Uiso 1 1 d . . . . .
H13B H -0.130(2) 0.3610(10) 0.427(4) 0.042(6) Uiso 1 1 d . . . . .
H3AB H 0.569(3) 0.4108(11) 0.387(5) 0.052(7) Uiso 1 1 d . . . . .
H3AC H 0.546(2) 0.4561(10) 0.552(4) 0.042(6) Uiso 1 1 d . . . . .
H13C H -0.045(2) 0.3681(11) 0.214(5) 0.054(7) Uiso 1 1 d . . . . .
H8AB H 0.262(2) 0.2326(10) 1.182(4) 0.044(7) Uiso 1 1 d . . . . .
H8AC H 0.121(3) 0.2269(10) 1.166(4) 0.041(6) Uiso 1 1 d . . . . .
H10B H -0.039(2) 0.2788(9) 0.546(3) 0.036(6) Uiso 1 1 d . . . . .
H9AB H 0.021(2) 0.2246(9) 0.823(4) 0.034(5) Uiso 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O2A C1A 1.3435(16) . ?
O2A C6A 1.4611(15) . ?
O3A C7A 1.4453(15) . ?
O3A C6A 1.3880(14) . ?
O5A O4A 1.4725(14) . ?
O5A C5A 1.4575(14) . ?
O4A C7A 1.4140(19) . ?
O2B C1B 1.3178(18) . ?
O2B H2B 0.92(2) . ?
O1B C1B 1.2014(17) . ?
O1A C1A 1.2104(17) . ?
C1B C2B 1.4658(19) . ?
C4A C15A 1.5329(18) . ?
C4A C5A 1.5320(17) . ?
C4A C2A 1.5339(19) . ?
C4A H4A 1.01(2) . ?
C1A C2A 1.5123(19) . ?
C15A C14A 1.528(2) . ?
C15A H15A 1.03(2) . ?
C15A H15B 0.95(2) . ?
C2B C2B 1.194(3) 2_765 ?
C7A C9A 1.539(2) . ?
C7A C8A 1.516(2) . ?
C5A C6A 1.5252(16) . ?
C5A C11A 1.5390(18) . ?
C6A H6A 0.976(17) . ?
C14A C12A 1.530(2) . ?
C14A H14A 0.99(2) . ?
C14A H14B 0.99(2) . ?
C2A C3A 1.525(2) . ?
C2A H2A 0.96(2) . ?
C12A C11A 1.5443(18) . ?
C12A C13A 1.532(2) . ?
C12A H12A 0.973(18) . ?
C11A C10A 1.539(2) . ?
C11A H11A 0.98(2) . ?
C10A C9A 1.531(2) . ?
C10A H10A 0.97(2) . ?
C10A H10B 1.02(2) . ?
C9A H9AA 0.97(2) . ?
C9A H9AB 0.99(2) . ?
C3A H3AA 0.98(3) . ?
C3A H3AB 0.96(3) . ?
C3A H3AC 0.97(2) . ?
C13A H13A 1.01(3) . ?
C13A H13B 1.01(2) . ?
C13A H13C 1.01(3) . ?
C8A H8AA 0.95(2) . ?
C8A H8AB 0.92(3) . ?
C8A H8AC 0.96(3) . ?

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
C1A O2A C6A 123.47(10) . . ?
C6A O3A C7A 113.69(10) . . ?
C5A O5A O4A 111.33(9) . . ?
C7A O4A O5A 107.49(10) . . ?
C1B O2B H2B 108.0(15) . . ?
O2B C1B C2B 112.47(12) . . ?
O1B C1B O2B 125.97(14) . . ?
O1B C1B C2B 121.55(14) . . ?
C15A C4A C2A 114.29(10) . . ?
C15A C4A H4A 106.6(11) . . ?
C5A C4A C15A 111.49(11) . . ?
C5A C4A C2A 109.03(10) . . ?
C5A C4A H4A 107.7(11) . . ?
C2A C4A H4A 107.5(11) . . ?
O2A C1A C2A 118.20(12) . . ?
O1A C1A O2A 116.57(12) . . ?
O1A C1A C2A 125.00(13) . . ?
C4A C15A H15A 110.0(11) . . ?
C4A C15A H15B 108.6(12) . . ?
C14A C15A C4A 110.83(11) . . ?
C14A C15A H15A 111.2(11) . . ?
C14A C15A H15B 111.9(12) . . ?
H15A C15A H15B 104.1(16) . . ?
C2B C2B C1B 175.74(19) 2_765 . ?
O3A C7A C9A 110.10(11) . . ?
O3A C7A C8A 106.48(11) . . ?
O4A C7A O3A 107.36(10) . . ?
O4A C7A C9A 112.68(12) . . ?
O4A C7A C8A 105.61(12) . . ?
C8A C7A C9A 114.18(12) . . ?
O5A C5A C4A 104.28(10) . . ?
O5A C5A C6A 111.27(9) . . ?
O5A C5A C11A 106.94(9) . . ?
C4A C5A C11A 112.67(10) . . ?
C6A C5A C4A 110.97(9) . . ?
C6A C5A C11A 110.49(10) . . ?
O2A C6A C5A 114.58(10) . . ?
O2A C6A H6A 103.9(11) . . ?
O3A C6A O2A 106.06(9) . . ?
O3A C6A C5A 114.62(9) . . ?
O3A C6A H6A 105.8(10) . . ?
C5A C6A H6A 111.0(11) . . ?
C15A C14A C12A 112.99(11) . . ?
C15A C14A H14A 107.6(12) . . ?
C15A C14A H14B 108.6(12) . . ?
C12A C14A H14A 109.6(13) . . ?
C12A C14A H14B 108.6(13) . . ?
H14A C14A H14B 109.3(19) . . ?
C4A C2A H2A 106.3(13) . . ?
C1A C2A C4A 112.40(11) . . ?
C1A C2A C3A 112.17(12) . . ?
C1A C2A H2A 104.3(12) . . ?
C3A C2A C4A 114.16(11) . . ?
C3A C2A H2A 106.7(12) . . ?
C14A C12A C11A 111.33(11) . . ?
C14A C12A C13A 110.07(12) . . ?
C14A C12A H12A 111.8(10) . . ?
C11A C12A H12A 105.1(10) . . ?
C13A C12A C11A 111.40(12) . . ?
C13A C12A H12A 106.9(11) . . ?
C5A C11A C12A 112.00(10) . . ?
C5A C11A H11A 103.9(12) . . ?
C12A C11A H11A 108.6(11) . . ?
C10A C11A C5A 111.92(11) . . ?
C10A C11A C12A 111.01(12) . . ?
C10A C11A H11A 109.1(11) . . ?
C11A C10A H10A 109.6(12) . . ?
C11A C10A H10B 110.5(12) . . ?
C9A C10A C11A 116.28(13) . . ?
C9A C10A H10A 107.2(12) . . ?
C9A C10A H10B 105.9(12) . . ?
H10A C10A H10B 106.8(17) . . ?
C7A C9A H9AA 107.1(12) . . ?
C7A C9A H9AB 108.6(13) . . ?
C10A C9A C7A 114.30(11) . . ?
C10A C9A H9AA 110.7(12) . . ?
C10A C9A H9AB 107.4(13) . . ?
H9AA C9A H9AB 108.5(18) . . ?
C2A C3A H3AA 109.5(14) . . ?
C2A C3A H3AB 110.3(16) . . ?
C2A C3A H3AC 110.3(15) . . ?
H3AA C3A H3AB 109(2) . . ?
H3AA C3A H3AC 111(2) . . ?
H3AB C3A H3AC 107(2) . . ?
C12A C13A H13A 110.8(15) . . ?
C12A C13A H13B 112.4(13) . . ?
C12A C13A H13C 110.5(15) . . ?
H13A C13A H13B 106.2(19) . . ?
H13A C13A H13C 106(2) . . ?
H13B C13A H13C 111(2) . . ?
C7A C8A H8AA 109.7(14) . . ?
C7A C8A H8AB 112.2(15) . . ?
C7A C8A H8AC 108.2(15) . . ?
H8AA C8A H8AB 111.5(19) . . ?
H8AA C8A H8AC 110(2) . . ?
H8AB C8A H8AC 105(2) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O2B H2B O1A 0.92(2) 1.74(2) 2.6523(16) 174(2) .
C8A H8AA O1B 0.95(2) 2.65(2) 3.4364(19) 140.9(18) 4_457

_olex2_submission_special_instructions 'No special instructions were received'


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Chloroform/Methanol (90%:10%)'
