# 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_la088
_database_code_depnum_ccdc_archive 'CCDC 2144421'
loop_
_audit_author_name
_audit_author_address
'Eric C. Hosten'
;Nelson Mandela University
South Africa
;
_audit_update_record             
;
2022-01-25 deposited with the CCDC.	2022-05-30 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        
'trans-9,10-dihydro-9,10-ethanoanthracene-11,12-dicarboxylic acid'
_chemical_name_common            ?
_chemical_melting_point          513.15
_chemical_formula_moiety         'C18 H14 O4, 2(C6 H7 N)'
_chemical_formula_sum            'C30 H28 N2 O4'
_chemical_formula_weight         480.54

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'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/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                   9.5395(5)
_cell_length_b                   13.2797(7)
_cell_length_c                   20.6305(12)
_cell_angle_alpha                90
_cell_angle_beta                 99.679(3)
_cell_angle_gamma                90
_cell_volume                     2576.3(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    200(2)
_cell_measurement_reflns_used    9552
_cell_measurement_theta_min      2.52
_cell_measurement_theta_max      28.25

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.239
_exptl_crystal_F_000             1016
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.825
_exptl_crystal_size_mid          0.599
_exptl_crystal_size_min          0.579
_exptl_absorpt_coefficient_mu    0.083
_shelx_estimated_absorpt_T_min   0.935
_shelx_estimated_absorpt_T_max   0.954
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_correction_T_min  0.9297
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_process_details   'SADABS V2008/1 (Bruker AXS)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      200(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean 8.3333
_diffrn_reflns_number            78775
_diffrn_reflns_av_unetI/netI     0.0127
_diffrn_reflns_av_R_equivalents  0.0265
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_theta_min         1.831
_diffrn_reflns_theta_max         28.308
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             6411
_reflns_number_gt                5074
_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       'Bruker Instrument Service v2011.4.0.0'
_computing_cell_refinement       'APEX2 v2011.4-1 (Bruker AXS)'
_computing_data_reduction        'SAINT V7.68A (Bruker AXS, 2009)'
_computing_structure_solution    'SHELXT-2018/2 (Sheldrick, 2015)'
_computing_structure_refinement  
'SHELXL-2018/3 (Sheldrick, 2015) and ShelXle (Hübschle, 2011)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 2012)'
_computing_publication_material  
'PLATON (Spek, 2009) and MERCURY (Macrae, 2008)'

_refine_special_details          
;
Carbon-bound H atoms were placed in calculated positions and were included in
the refinement in the riding model approximation, with Uiso(H) set to
1.2 Ueq(C).

The H atoms of the methyl groups were allowed to rotate with a fixed angle
around the C---C bonds to best fit the experimental electron density (HFIX 137
in the SHELXL program (Sheldrick, 2015)), with Uiso(H) set to
1.5Ueq(C).

The H atoms of the hydroxyl groups were allowed to rotate with a fixed angle
around the C---O bonds to best fit the experimental electron density (HFIX 147
in the SHELXL program (Sheldrick, 2015)), with Uiso(H) set to
1.5Ueq(O).
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0575P)²+0.8627P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_extinction_coef       0.0025(7)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         6411
_refine_ls_number_parameters     330
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0603
_refine_ls_R_factor_gt           0.0457
_refine_ls_wR_factor_ref         0.1334
_refine_ls_wR_factor_gt          0.1180
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_restrained_S_all      1.051
_refine_ls_shift/su_max          0.001
_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 0.25424(11) 1.00567(7) 0.37650(6) 0.0475(3) Uani 1 1 d . . . . .
H1A H 0.173367 1.016770 0.385951 0.071 Uiso 1 1 calc R U . . .
O2 O 0.19232(11) 0.84610(8) 0.38771(6) 0.0529(3) Uani 1 1 d . . . . .
O3 O 0.56747(14) 0.62508(8) 0.38321(6) 0.0612(3) Uani 1 1 d . . . . .
H3A H 0.621732 0.599469 0.415254 0.092 Uiso 1 1 calc R U . . .
O4 O 0.61284(15) 0.76480(9) 0.44166(6) 0.0655(4) Uani 1 1 d . . . . .
N3 N 0.49480(13) 0.54710(9) 0.09565(6) 0.0434(3) Uani 1 1 d . . . . .
N4 N 0.73327(17) 0.53513(10) 0.48157(8) 0.0578(4) Uani 1 1 d . . . . .
C1 C 0.44129(13) 0.94177(9) 0.29223(6) 0.0310(2) Uani 1 1 d . . . . .
H1 H 0.434601 1.016229 0.298283 0.037 Uiso 1 1 calc R U . . .
C2 C 0.41821(13) 0.88228(9) 0.35509(6) 0.0316(3) Uani 1 1 d . . . . .
H2 H 0.494391 0.902972 0.392100 0.038 Uiso 1 1 calc R U . . .
C3 C 0.43402(14) 0.76825(9) 0.34374(7) 0.0342(3) Uani 1 1 d . . . . .
H3 H 0.341448 0.735515 0.347730 0.041 Uiso 1 1 calc R U . . .
C4 C 0.46188(14) 0.75024(9) 0.27193(7) 0.0357(3) Uani 1 1 d . . . . .
H4 H 0.470315 0.676990 0.262030 0.043 Uiso 1 1 calc R U . . .
C5 C 0.27517(14) 0.90830(9) 0.37415(6) 0.0352(3) Uani 1 1 d . . . . .
C6 C 0.54855(15) 0.72082(10) 0.39489(7) 0.0410(3) Uani 1 1 d . . . . .
C11 C 0.32904(13) 0.90341(9) 0.23722(6) 0.0328(3) Uani 1 1 d . . . . .
C12 C 0.34007(13) 0.79959(10) 0.22643(7) 0.0353(3) Uani 1 1 d . . . . .
C13 C 0.24414(15) 0.75299(11) 0.17790(8) 0.0466(3) Uani 1 1 d . . . . .
H13 H 0.250020 0.682606 0.170553 0.056 Uiso 1 1 calc R U . . .
C14 C 0.13911(17) 0.81034(14) 0.14002(9) 0.0576(4) Uani 1 1 d . . . . .
H14 H 0.074516 0.778971 0.105912 0.069 Uiso 1 1 calc R U . . .
C15 C 0.12729(16) 0.91226(13) 0.15123(8) 0.0532(4) Uani 1 1 d . . . . .
H15 H 0.054193 0.950278 0.125267 0.064 Uiso 1 1 calc R U . . .
C16 C 0.22202(14) 0.95921(11) 0.20038(7) 0.0400(3) Uani 1 1 d . . . . .
H16 H 0.213353 1.029120 0.208622 0.048 Uiso 1 1 calc R U . . .
C21 C 0.58465(13) 0.91070(9) 0.27678(6) 0.0330(3) Uani 1 1 d . . . . .
C22 C 0.59567(14) 0.80756(10) 0.26552(6) 0.0356(3) Uani 1 1 d . . . . .
C23 C 0.72112(16) 0.76800(12) 0.25115(8) 0.0474(3) Uani 1 1 d . . . . .
H23 H 0.729667 0.697634 0.244484 0.057 Uiso 1 1 calc R U . . .
C24 C 0.83457(17) 0.83182(15) 0.24651(9) 0.0571(4) Uani 1 1 d . . . . .
H24 H 0.920447 0.804974 0.236171 0.069 Uiso 1 1 calc R U . . .
C25 C 0.82309(16) 0.93398(14) 0.25687(8) 0.0536(4) Uani 1 1 d . . . . .
H25 H 0.900611 0.977239 0.253072 0.064 Uiso 1 1 calc R U . . .
C26 C 0.69831(15) 0.97381(11) 0.27284(7) 0.0416(3) Uani 1 1 d . . . . .
H26 H 0.691222 1.043877 0.280983 0.050 Uiso 1 1 calc R U . . .
C31 C 0.57370(16) 0.47371(11) 0.07649(7) 0.0442(3) Uani 1 1 d . . . . .
H21 H 0.538971 0.406593 0.075646 0.053 Uiso 1 1 calc R U . . .
C32 C 0.70465(15) 0.49123(11) 0.05770(7) 0.0433(3) Uani 1 1 d . . . . .
H32 H 0.757296 0.437090 0.043632 0.052 Uiso 1 1 calc R U . . .
C33 C 0.75761(15) 0.58826(11) 0.05967(7) 0.0406(3) Uani 1 1 d . . . . .
C34 C 0.67526(17) 0.66395(12) 0.08032(8) 0.0492(4) Uani 1 1 d . . . . .
H34 H 0.708095 0.731603 0.082615 0.059 Uiso 1 1 calc R U . . .
C35 C 0.54564(18) 0.64069(12) 0.09751(8) 0.0499(4) Uani 1 1 d . . . . .
H35 H 0.490231 0.693532 0.111239 0.060 Uiso 1 1 calc R U . . .
C36 C 0.89994(16) 0.61062(14) 0.04119(9) 0.0541(4) Uani 1 1 d . . . . .
H36A H 0.973877 0.605069 0.080227 0.081 Uiso 1 1 calc R U . . .
H36B H 0.899701 0.679072 0.023421 0.081 Uiso 1 1 calc R U . . .
H36C H 0.919222 0.562335 0.007861 0.081 Uiso 1 1 calc R U . . .
C41 C 0.91254(17) 0.43403(11) 0.58139(7) 0.0449(3) Uani 1 1 d . . . . .
C42 C 0.92456(19) 0.53682(12) 0.57178(8) 0.0526(4) Uani 1 1 d . . . . .
H42 H 0.995127 0.574689 0.599440 0.063 Uiso 1 1 calc R U . . .
C43 C 0.8336(2) 0.58380(12) 0.52189(9) 0.0550(4) Uani 1 1 d . . . . .
H43 H 0.843312 0.654285 0.516138 0.066 Uiso 1 1 calc R U . . .
C44 C 0.7211(2) 0.43659(13) 0.49160(10) 0.0635(5) Uani 1 1 d . . . . .
H44 H 0.648974 0.400655 0.463520 0.076 Uiso 1 1 calc R U . . .
C45 C 0.80675(18) 0.38409(12) 0.54019(8) 0.0528(4) Uani 1 1 d . . . . .
H45 H 0.793122 0.313867 0.545332 0.063 Uiso 1 1 calc R U . . .
C46 C 1.0096(2) 0.37850(15) 0.63420(9) 0.0644(5) Uani 1 1 d . . . . .
H46A H 1.016578 0.307950 0.621180 0.097 Uiso 1 1 calc R U . . .
H46B H 0.971354 0.381842 0.675371 0.097 Uiso 1 1 calc R U . . .
H46C H 1.104167 0.409411 0.640558 0.097 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 C5 1.3104(15) . ?
O1 H1A 0.8400 . ?
O2 C5 1.2081(16) . ?
O3 C6 1.3121(17) . ?
O3 H3A 0.8400 . ?
O4 C6 1.2039(19) . ?
N3 C31 1.3314(19) . ?
N3 C35 1.3322(19) . ?
N4 C43 1.326(2) . ?
N4 C44 1.333(2) . ?
C1 C11 1.5118(17) . ?
C1 C21 1.5129(17) . ?
C1 C2 1.5653(17) . ?
C1 H1 1.0000 . ?
C2 C5 1.5219(17) . ?
C2 C3 1.5434(16) . ?
C2 H2 1.0000 . ?
C3 C6 1.5220(19) . ?
C3 C4 1.5668(19) . ?
C3 H3 1.0000 . ?
C4 C22 1.5109(18) . ?
C4 C12 1.5146(18) . ?
C4 H4 1.0000 . ?
C11 C16 1.3813(18) . ?
C11 C12 1.4033(17) . ?
C12 C13 1.3839(19) . ?
C13 C14 1.390(2) . ?
C13 H13 0.9500 . ?
C14 C15 1.381(2) . ?
C14 H14 0.9500 . ?
C15 C16 1.388(2) . ?
C15 H15 0.9500 . ?
C16 H16 0.9500 . ?
C21 C26 1.3835(18) . ?
C21 C22 1.3961(18) . ?
C22 C23 1.3840(18) . ?
C23 C24 1.391(2) . ?
C23 H23 0.9500 . ?
C24 C25 1.381(3) . ?
C24 H24 0.9500 . ?
C25 C26 1.392(2) . ?
C25 H25 0.9500 . ?
C26 H26 0.9500 . ?
C31 C32 1.388(2) . ?
C31 H21 0.9500 . ?
C32 C33 1.382(2) . ?
C32 H32 0.9500 . ?
C33 C34 1.386(2) . ?
C33 C36 1.500(2) . ?
C34 C35 1.378(2) . ?
C34 H34 0.9500 . ?
C35 H35 0.9500 . ?
C36 H36A 0.9800 . ?
C36 H36B 0.9800 . ?
C36 H36C 0.9800 . ?
C41 C45 1.376(2) . ?
C41 C42 1.387(2) . ?
C41 C46 1.499(2) . ?
C42 C43 1.379(2) . ?
C42 H42 0.9500 . ?
C43 H43 0.9500 . ?
C44 C45 1.372(2) . ?
C44 H44 0.9500 . ?
C45 H45 0.9500 . ?
C46 H46A 0.9800 . ?
C46 H46B 0.9800 . ?
C46 H46C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C5 O1 H1A 109.5 . . ?
C6 O3 H3A 109.5 . . ?
C31 N3 C35 118.05(13) . . ?
C43 N4 C44 116.98(14) . . ?
C11 C1 C21 107.53(10) . . ?
C11 C1 C2 105.75(10) . . ?
C21 C1 C2 107.16(9) . . ?
C11 C1 H1 112.0 . . ?
C21 C1 H1 112.0 . . ?
C2 C1 H1 112.0 . . ?
C5 C2 C3 112.13(10) . . ?
C5 C2 C1 110.88(10) . . ?
C3 C2 C1 109.79(10) . . ?
C5 C2 H2 108.0 . . ?
C3 C2 H2 108.0 . . ?
C1 C2 H2 108.0 . . ?
C6 C3 C2 112.21(11) . . ?
C6 C3 C4 112.10(10) . . ?
C2 C3 C4 109.25(10) . . ?
C6 C3 H3 107.7 . . ?
C2 C3 H3 107.7 . . ?
C4 C3 H3 107.7 . . ?
C22 C4 C12 107.40(10) . . ?
C22 C4 C3 106.61(10) . . ?
C12 C4 C3 106.59(10) . . ?
C22 C4 H4 112.0 . . ?
C12 C4 H4 112.0 . . ?
C3 C4 H4 112.0 . . ?
O2 C5 O1 123.81(12) . . ?
O2 C5 C2 123.67(11) . . ?
O1 C5 C2 112.48(11) . . ?
O4 C6 O3 123.37(13) . . ?
O4 C6 C3 124.37(12) . . ?
O3 C6 C3 112.25(13) . . ?
C16 C11 C12 120.53(12) . . ?
C16 C11 C1 126.66(11) . . ?
C12 C11 C1 112.80(11) . . ?
C13 C12 C11 119.74(13) . . ?
C13 C12 C4 126.87(12) . . ?
C11 C12 C4 113.39(11) . . ?
C12 C13 C14 119.23(14) . . ?
C12 C13 H13 120.4 . . ?
C14 C13 H13 120.4 . . ?
C15 C14 C13 120.96(14) . . ?
C15 C14 H14 119.5 . . ?
C13 C14 H14 119.5 . . ?
C14 C15 C16 120.09(14) . . ?
C14 C15 H15 120.0 . . ?
C16 C15 H15 120.0 . . ?
C11 C16 C15 119.43(13) . . ?
C11 C16 H16 120.3 . . ?
C15 C16 H16 120.3 . . ?
C26 C21 C22 120.19(12) . . ?
C26 C21 C1 126.32(12) . . ?
C22 C21 C1 113.49(11) . . ?
C23 C22 C21 120.00(13) . . ?
C23 C22 C4 126.95(13) . . ?
C21 C22 C4 113.04(11) . . ?
C22 C23 C24 119.63(15) . . ?
C22 C23 H23 120.2 . . ?
C24 C23 H23 120.2 . . ?
C25 C24 C23 120.36(14) . . ?
C25 C24 H24 119.8 . . ?
C23 C24 H24 119.8 . . ?
C24 C25 C26 120.22(14) . . ?
C24 C25 H25 119.9 . . ?
C26 C25 H25 119.9 . . ?
C21 C26 C25 119.58(14) . . ?
C21 C26 H26 120.2 . . ?
C25 C26 H26 120.2 . . ?
N3 C31 C32 122.70(14) . . ?
N3 C31 H21 118.7 . . ?
C32 C31 H21 118.7 . . ?
C33 C32 C31 119.32(14) . . ?
C33 C32 H32 120.3 . . ?
C31 C32 H32 120.3 . . ?
C32 C33 C34 117.50(13) . . ?
C32 C33 C36 121.27(14) . . ?
C34 C33 C36 121.22(14) . . ?
C35 C34 C33 119.74(14) . . ?
C35 C34 H34 120.1 . . ?
C33 C34 H34 120.1 . . ?
N3 C35 C34 122.68(15) . . ?
N3 C35 H35 118.7 . . ?
C34 C35 H35 118.7 . . ?
C33 C36 H36A 109.5 . . ?
C33 C36 H36B 109.5 . . ?
H36A C36 H36B 109.5 . . ?
C33 C36 H36C 109.5 . . ?
H36A C36 H36C 109.5 . . ?
H36B C36 H36C 109.5 . . ?
C45 C41 C42 117.12(14) . . ?
C45 C41 C46 120.73(15) . . ?
C42 C41 C46 122.15(15) . . ?
C43 C42 C41 119.69(16) . . ?
C43 C42 H42 120.2 . . ?
C41 C42 H42 120.2 . . ?
N4 C43 C42 123.03(15) . . ?
N4 C43 H43 118.5 . . ?
C42 C43 H43 118.5 . . ?
N4 C44 C45 123.73(16) . . ?
N4 C44 H44 118.1 . . ?
C45 C44 H44 118.1 . . ?
C44 C45 C41 119.43(15) . . ?
C44 C45 H45 120.3 . . ?
C41 C45 H45 120.3 . . ?
C41 C46 H46A 109.5 . . ?
C41 C46 H46B 109.5 . . ?
H46A C46 H46B 109.5 . . ?
C41 C46 H46C 109.5 . . ?
H46A C46 H46C 109.5 . . ?
H46B C46 H46C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C11 C1 C2 C5 -65.08(12) . . . . ?
C21 C1 C2 C5 -179.57(10) . . . . ?
C11 C1 C2 C3 59.37(12) . . . . ?
C21 C1 C2 C3 -55.12(13) . . . . ?
C5 C2 C3 C6 -113.56(12) . . . . ?
C1 C2 C3 C6 122.71(11) . . . . ?
C5 C2 C3 C4 121.48(11) . . . . ?
C1 C2 C3 C4 -2.25(14) . . . . ?
C6 C3 C4 C22 -66.30(13) . . . . ?
C2 C3 C4 C22 58.72(13) . . . . ?
C6 C3 C4 C12 179.21(10) . . . . ?
C2 C3 C4 C12 -55.77(13) . . . . ?
C3 C2 C5 O2 9.65(19) . . . . ?
C1 C2 C5 O2 132.76(14) . . . . ?
C3 C2 C5 O1 -172.66(11) . . . . ?
C1 C2 C5 O1 -49.55(15) . . . . ?
C2 C3 C6 O4 5.0(2) . . . . ?
C4 C3 C6 O4 128.39(16) . . . . ?
C2 C3 C6 O3 -176.51(12) . . . . ?
C4 C3 C6 O3 -53.14(16) . . . . ?
C21 C1 C11 C16 -127.08(13) . . . . ?
C2 C1 C11 C16 118.69(13) . . . . ?
C21 C1 C11 C12 54.33(13) . . . . ?
C2 C1 C11 C12 -59.91(13) . . . . ?
C16 C11 C12 C13 0.9(2) . . . . ?
C1 C11 C12 C13 179.58(12) . . . . ?
C16 C11 C12 C4 -179.02(12) . . . . ?
C1 C11 C12 C4 -0.33(15) . . . . ?
C22 C4 C12 C13 125.95(14) . . . . ?
C3 C4 C12 C13 -120.10(14) . . . . ?
C22 C4 C12 C11 -54.16(14) . . . . ?
C3 C4 C12 C11 59.80(14) . . . . ?
C11 C12 C13 C14 0.7(2) . . . . ?
C4 C12 C13 C14 -179.36(14) . . . . ?
C12 C13 C14 C15 -1.6(3) . . . . ?
C13 C14 C15 C16 0.8(3) . . . . ?
C12 C11 C16 C15 -1.7(2) . . . . ?
C1 C11 C16 C15 179.81(13) . . . . ?
C14 C15 C16 C11 0.9(2) . . . . ?
C11 C1 C21 C26 125.37(13) . . . . ?
C2 C1 C21 C26 -121.34(13) . . . . ?
C11 C1 C21 C22 -54.18(13) . . . . ?
C2 C1 C21 C22 59.11(13) . . . . ?
C26 C21 C22 C23 0.8(2) . . . . ?
C1 C21 C22 C23 -179.65(12) . . . . ?
C26 C21 C22 C4 179.93(12) . . . . ?
C1 C21 C22 C4 -0.48(16) . . . . ?
C12 C4 C22 C23 -126.40(14) . . . . ?
C3 C4 C22 C23 119.66(14) . . . . ?
C12 C4 C22 C21 54.50(14) . . . . ?
C3 C4 C22 C21 -59.44(14) . . . . ?
C21 C22 C23 C24 -1.5(2) . . . . ?
C4 C22 C23 C24 179.49(14) . . . . ?
C22 C23 C24 C25 0.7(2) . . . . ?
C23 C24 C25 C26 0.8(3) . . . . ?
C22 C21 C26 C25 0.7(2) . . . . ?
C1 C21 C26 C25 -178.81(13) . . . . ?
C24 C25 C26 C21 -1.5(2) . . . . ?
C35 N3 C31 C32 -0.9(2) . . . . ?
N3 C31 C32 C33 1.0(2) . . . . ?
C31 C32 C33 C34 -0.3(2) . . . . ?
C31 C32 C33 C36 178.71(13) . . . . ?
C32 C33 C34 C35 -0.4(2) . . . . ?
C36 C33 C34 C35 -179.40(15) . . . . ?
C31 N3 C35 C34 0.2(2) . . . . ?
C33 C34 C35 N3 0.5(3) . . . . ?
C45 C41 C42 C43 -0.9(2) . . . . ?
C46 C41 C42 C43 179.15(16) . . . . ?
C44 N4 C43 C42 1.0(3) . . . . ?
C41 C42 C43 N4 -0.2(3) . . . . ?
C43 N4 C44 C45 -0.8(3) . . . . ?
N4 C44 C45 C41 -0.3(3) . . . . ?
C42 C41 C45 C44 1.1(3) . . . . ?
C46 C41 C45 C44 -178.92(18) . . . . ?

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
_geom_hbond_publ_flag
O1 H1A N3 0.84 1.76 2.5954(15) 177 2 yes
O3 H3A N4 0.84 1.80 2.6396(18) 176 . yes
C2 H2 O4 1.00 2.30 2.8206(16) 111 . yes
C3 H3 O2 1.00 2.29 2.8126(16) 111 . yes
C13 H13 O1 0.95 2.54 3.4716(18) 167 2_545 yes
C15 H15 O3 0.95 2.59 3.391(2) 143 2 yes
C31 H21 O2 0.95 2.58 3.2384(18) 127 2_545 yes
C32 H32 O4 0.95 2.60 3.474(2) 154 2_645 yes
C45 H45 O2 0.95 2.53 3.3989(19) 153 3_666 yes

_refine_diff_density_max         0.262
_refine_diff_density_min         -0.201
_refine_diff_density_rms         0.038


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: 4-methylpyridine'
####################################################################### 
# 
# 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_ma033
_database_code_depnum_ccdc_archive 'CCDC 2153572'
loop_
_audit_author_name
_audit_author_address
'Eric Hosten'
;Nelson Mandela University
South Africa
;
_audit_update_record             
;
2022-02-21 deposited with the CCDC.	2022-05-30 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        
'trans-9,10-dihydro-9,10-ethanoanthracene-11,12-dicarboxylic acid'
_chemical_name_common            ?
_chemical_melting_point          513.15
_chemical_formula_moiety         'C18 H13 O4, C6 H8 N'
_chemical_formula_sum            'C24 H21 N O4'
_chemical_formula_weight         387.42

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'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           33
_space_group_name_H-M_alt        'P n a 21'
_space_group_name_Hall           'P 2c -2n'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z+1/2'
'x+1/2, -y+1/2, z'
'-x+1/2, y+1/2, z+1/2'

_cell_length_a                   16.5185(6)
_cell_length_b                   9.3246(3)
_cell_length_c                   12.6580(5)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1949.69(12)
_cell_formula_units_Z            4
_cell_measurement_temperature    200(2)
_cell_measurement_reflns_used    9922
_cell_measurement_theta_min      2.47
_cell_measurement_theta_max      28.23

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.320
_exptl_crystal_F_000             816
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.599
_exptl_crystal_size_mid          0.503
_exptl_crystal_size_min          0.426
_exptl_absorpt_coefficient_mu    0.090
_shelx_estimated_absorpt_T_min   0.948
_shelx_estimated_absorpt_T_max   0.963
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_correction_T_min  0.9143
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_process_details   'SADABS V2008/1 (Bruker AXS)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      200(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean 8.3333
_diffrn_reflns_number            24702
_diffrn_reflns_av_unetI/netI     0.0174
_diffrn_reflns_av_R_equivalents  0.0212
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.466
_diffrn_reflns_theta_max         28.329
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             4846
_reflns_number_gt                4489
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.911
_reflns_Friedel_fraction_max     0.994
_reflns_Friedel_fraction_full    0.999

_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       'Bruker Instrument Service v2011.4.0.0'
_computing_cell_refinement       'APEX2 v2011.4-1 (Bruker AXS)'
_computing_data_reduction        'SAINT V7.68A (Bruker AXS, 2009)'
_computing_structure_solution    'SHELXT-2018/2 (Sheldrick, 2015)'
_computing_structure_refinement  
'SHELXL-2018/3 (Sheldrick, 2015) and ShelXle (Hübschle, 2011)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 2012)'
_computing_publication_material  
'PLATON (Spek, 2009) and MERCURY (Macrae, 2008)'

_refine_special_details          
;
Carbon-bound H atoms were placed in calculated positions and were included in
the refinement in the riding model approximation, with Uiso(H) set to
1.2 Ueq(C).

The H atoms of the methyl groups were allowed to rotate with a fixed angle
around the C---C bonds to best fit the experimental electron density (HFIX 137
in the SHELXL program (Sheldrick, 2015)), with Uiso(H) set to
1.5Ueq(C).

The H atoms of the hydroxyl groups were allowed to rotate with a fixed angle
around the C---O bonds to best fit the experimental electron density (HFIX 147
in the SHELXL program (Sheldrick, 2015)), with Uiso(H) allowed to
refine.

The nitrogen-bound H atom was located on a difference map and refined freely.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0516P)²+0.1874P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 2032 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.1(2)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         4846
_refine_ls_number_parameters     269
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0355
_refine_ls_R_factor_gt           0.0317
_refine_ls_wR_factor_ref         0.0838
_refine_ls_wR_factor_gt          0.0810
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_restrained_S_all      1.038
_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 0.51347(9) 0.24135(14) 0.66574(10) 0.0320(3) Uani 1 1 d . . . . .
O2 O 0.52476(9) 0.17409(14) 0.49892(10) 0.0338(3) Uani 1 1 d . . . . .
O3 O 0.45171(8) 0.53214(16) 0.38148(11) 0.0349(3) Uani 1 1 d . . . . .
O4 O 0.55639(9) 0.57445(18) 0.27468(11) 0.0398(3) Uani 1 1 d . . . . .
H4A H 0.522635 0.625873 0.242613 0.058(9) Uiso 1 1 calc R . . . .
N3 N 0.43493(10) 0.96636(17) 0.58320(14) 0.0321(3) Uani 1 1 d . . . . .
C1 C 0.62371(10) 0.47197(18) 0.61954(13) 0.0249(3) Uani 1 1 d . . . . .
H1 H 0.608482 0.459485 0.695444 0.030 Uiso 1 1 calc R U . . .
C2 C 0.55521(9) 0.41998(17) 0.54289(12) 0.0206(3) Uani 1 1 d . . . . .
H2 H 0.507073 0.483197 0.554096 0.025 Uiso 1 1 calc R U . . .
C3 C 0.58333(9) 0.43952(17) 0.42747(13) 0.0221(3) Uani 1 1 d . . . . .
H3A H 0.588752 0.341564 0.396092 0.027 Uiso 1 1 calc R U . . .
C4 C 0.66952(10) 0.50982(18) 0.42570(14) 0.0250(3) Uani 1 1 d . . . . .
H4 H 0.689381 0.526197 0.352055 0.030 Uiso 1 1 calc R U . . .
C5 C 0.53013(10) 0.26676(18) 0.57000(13) 0.0232(3) Uani 1 1 d . . . . .
C6 C 0.52281(10) 0.52134(18) 0.36019(12) 0.0239(3) Uani 1 1 d . . . . .
C11 C 0.69765(10) 0.38487(19) 0.59010(14) 0.0275(3) Uani 1 1 d . . . . .
C12 C 0.72249(10) 0.40522(18) 0.48550(14) 0.0273(3) Uani 1 1 d . . . . .
C13 C 0.78461(11) 0.3240(2) 0.44336(17) 0.0363(4) Uani 1 1 d . . . . .
H13 H 0.800803 0.337151 0.372005 0.044 Uiso 1 1 calc R U . . .
C14 C 0.82326(12) 0.2225(2) 0.5067(2) 0.0448(5) Uani 1 1 d . . . . .
H14 H 0.866063 0.166320 0.478362 0.054 Uiso 1 1 calc R U . . .
C15 C 0.79957(13) 0.2034(2) 0.6101(2) 0.0447(5) Uani 1 1 d . . . . .
H15 H 0.826704 0.134991 0.652951 0.054 Uiso 1 1 calc R U . . .
C16 C 0.73611(12) 0.2838(2) 0.65253(17) 0.0366(4) Uani 1 1 d . . . . .
H16 H 0.719464 0.269180 0.723566 0.044 Uiso 1 1 calc R U . . .
C21 C 0.63812(10) 0.62742(19) 0.59147(14) 0.0274(3) Uani 1 1 d . . . . .
C22 C 0.66277(10) 0.64801(18) 0.48727(14) 0.0267(3) Uani 1 1 d . . . . .
C23 C 0.67457(12) 0.7860(2) 0.44899(17) 0.0352(4) Uani 1 1 d . . . . .
H23 H 0.690806 0.800721 0.377819 0.042 Uiso 1 1 calc R U . . .
C24 C 0.66238(14) 0.9025(2) 0.51586(19) 0.0429(5) Uani 1 1 d . . . . .
H24 H 0.671410 0.997115 0.490543 0.051 Uiso 1 1 calc R U . . .
C25 C 0.63728(14) 0.8816(2) 0.6187(2) 0.0435(5) Uani 1 1 d . . . . .
H25 H 0.628475 0.961992 0.663315 0.052 Uiso 1 1 calc R U . . .
C26 C 0.62474(12) 0.7437(2) 0.65761(18) 0.0361(4) Uani 1 1 d . . . . .
H26 H 0.607301 0.729488 0.728349 0.043 Uiso 1 1 calc R U . . .
C31 C 0.41387(12) 0.8619(2) 0.51633(15) 0.0327(4) Uani 1 1 d . . . . .
C32 C 0.36995(13) 0.7465(2) 0.55544(18) 0.0393(5) Uani 1 1 d . . . . .
H32 H 0.355834 0.669118 0.510261 0.047 Uiso 1 1 calc R U . . .
C33 C 0.34706(15) 0.7449(2) 0.6596(2) 0.0463(5) Uani 1 1 d . . . . .
H33 H 0.316717 0.666389 0.686431 0.056 Uiso 1 1 calc R U . . .
C34 C 0.36791(16) 0.8566(3) 0.72536(19) 0.0471(5) Uani 1 1 d . . . . .
H34 H 0.351275 0.857054 0.797201 0.057 Uiso 1 1 calc R U . . .
C35 C 0.41298(14) 0.9667(2) 0.68526(16) 0.0404(5) Uani 1 1 d . . . . .
H35 H 0.428825 1.043775 0.729774 0.049 Uiso 1 1 calc R U . . .
C36 C 0.44112(18) 0.8775(3) 0.40411(18) 0.0501(6) Uani 1 1 d . . . . .
H36A H 0.499277 0.857719 0.399467 0.075 Uiso 1 1 calc R U . . .
H36B H 0.430415 0.975471 0.379863 0.075 Uiso 1 1 calc R U . . .
H36C H 0.411488 0.809430 0.359540 0.075 Uiso 1 1 calc R U . . .
H3 H 0.4668(16) 1.038(3) 0.554(2) 0.046(7) Uiso 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C5 1.265(2) . ?
O2 C5 1.251(2) . ?
O3 C6 1.209(2) . ?
O4 C6 1.313(2) . ?
O4 H4A 0.8400 . ?
N3 C31 1.336(3) . ?
N3 C35 1.342(3) . ?
N3 H3 0.93(3) . ?
C1 C21 1.511(2) . ?
C1 C11 1.513(2) . ?
C1 C2 1.567(2) . ?
C1 H1 1.0000 . ?
C2 C5 1.527(2) . ?
C2 C3 1.544(2) . ?
C2 H2 1.0000 . ?
C3 C6 1.519(2) . ?
C3 C4 1.568(2) . ?
C3 H3A 1.0000 . ?
C4 C22 1.510(2) . ?
C4 C12 1.513(2) . ?
C4 H4 1.0000 . ?
C11 C16 1.385(3) . ?
C11 C12 1.399(2) . ?
C12 C13 1.382(3) . ?
C13 C14 1.395(3) . ?
C13 H13 0.9500 . ?
C14 C15 1.378(4) . ?
C14 H14 0.9500 . ?
C15 C16 1.396(3) . ?
C15 H15 0.9500 . ?
C16 H16 0.9500 . ?
C21 C26 1.388(3) . ?
C21 C22 1.394(3) . ?
C22 C23 1.389(3) . ?
C23 C24 1.392(3) . ?
C23 H23 0.9500 . ?
C24 C25 1.380(3) . ?
C24 H24 0.9500 . ?
C25 C26 1.392(3) . ?
C25 H25 0.9500 . ?
C26 H26 0.9500 . ?
C31 C32 1.389(3) . ?
C31 C36 1.497(3) . ?
C32 C33 1.371(3) . ?
C32 H32 0.9500 . ?
C33 C34 1.377(4) . ?
C33 H33 0.9500 . ?
C34 C35 1.366(3) . ?
C34 H34 0.9500 . ?
C35 H35 0.9500 . ?
C36 H36A 0.9800 . ?
C36 H36B 0.9800 . ?
C36 H36C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C6 O4 H4A 109.5 . . ?
C31 N3 C35 122.77(18) . . ?
C31 N3 H3 114.8(17) . . ?
C35 N3 H3 122.4(17) . . ?
C21 C1 C11 109.25(14) . . ?
C21 C1 C2 105.36(13) . . ?
C11 C1 C2 105.32(13) . . ?
C21 C1 H1 112.2 . . ?
C11 C1 H1 112.2 . . ?
C2 C1 H1 112.2 . . ?
C5 C2 C3 113.88(13) . . ?
C5 C2 C1 110.26(13) . . ?
C3 C2 C1 109.40(13) . . ?
C5 C2 H2 107.7 . . ?
C3 C2 H2 107.7 . . ?
C1 C2 H2 107.7 . . ?
C6 C3 C2 113.07(13) . . ?
C6 C3 C4 112.32(13) . . ?
C2 C3 C4 109.64(12) . . ?
C6 C3 H3A 107.2 . . ?
C2 C3 H3A 107.2 . . ?
C4 C3 H3A 107.2 . . ?
C22 C4 C12 109.55(14) . . ?
C22 C4 C3 106.40(13) . . ?
C12 C4 C3 104.38(13) . . ?
C22 C4 H4 112.0 . . ?
C12 C4 H4 112.0 . . ?
C3 C4 H4 112.0 . . ?
O2 C5 O1 122.98(16) . . ?
O2 C5 C2 120.28(15) . . ?
O1 C5 C2 116.72(14) . . ?
O3 C6 O4 124.23(16) . . ?
O3 C6 C3 123.79(15) . . ?
O4 C6 C3 111.94(14) . . ?
C16 C11 C12 119.87(18) . . ?
C16 C11 C1 126.53(18) . . ?
C12 C11 C1 113.39(15) . . ?
C13 C12 C11 120.56(17) . . ?
C13 C12 C4 126.11(17) . . ?
C11 C12 C4 113.03(15) . . ?
C12 C13 C14 119.3(2) . . ?
C12 C13 H13 120.3 . . ?
C14 C13 H13 120.3 . . ?
C15 C14 C13 120.2(2) . . ?
C15 C14 H14 119.9 . . ?
C13 C14 H14 119.9 . . ?
C14 C15 C16 120.64(19) . . ?
C14 C15 H15 119.7 . . ?
C16 C15 H15 119.7 . . ?
C11 C16 C15 119.4(2) . . ?
C11 C16 H16 120.3 . . ?
C15 C16 H16 120.3 . . ?
C26 C21 C22 120.65(17) . . ?
C26 C21 C1 125.64(17) . . ?
C22 C21 C1 113.62(15) . . ?
C23 C22 C21 119.93(17) . . ?
C23 C22 C4 126.89(17) . . ?
C21 C22 C4 113.11(15) . . ?
C22 C23 C24 119.40(19) . . ?
C22 C23 H23 120.3 . . ?
C24 C23 H23 120.3 . . ?
C25 C24 C23 120.42(18) . . ?
C25 C24 H24 119.8 . . ?
C23 C24 H24 119.8 . . ?
C24 C25 C26 120.6(2) . . ?
C24 C25 H25 119.7 . . ?
C26 C25 H25 119.7 . . ?
C21 C26 C25 119.0(2) . . ?
C21 C26 H26 120.5 . . ?
C25 C26 H26 120.5 . . ?
N3 C31 C32 118.34(19) . . ?
N3 C31 C36 116.88(18) . . ?
C32 C31 C36 124.77(19) . . ?
C33 C32 C31 119.7(2) . . ?
C33 C32 H32 120.2 . . ?
C31 C32 H32 120.2 . . ?
C32 C33 C34 120.2(2) . . ?
C32 C33 H33 119.9 . . ?
C34 C33 H33 119.9 . . ?
C35 C34 C33 118.7(2) . . ?
C35 C34 H34 120.7 . . ?
C33 C34 H34 120.7 . . ?
N3 C35 C34 120.2(2) . . ?
N3 C35 H35 119.9 . . ?
C34 C35 H35 119.9 . . ?
C31 C36 H36A 109.5 . . ?
C31 C36 H36B 109.5 . . ?
H36A C36 H36B 109.5 . . ?
C31 C36 H36C 109.5 . . ?
H36A C36 H36C 109.5 . . ?
H36B C36 H36C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C21 C1 C2 C5 -175.21(13) . . . . ?
C11 C1 C2 C5 69.34(16) . . . . ?
C21 C1 C2 C3 58.81(16) . . . . ?
C11 C1 C2 C3 -56.64(17) . . . . ?
C5 C2 C3 C6 107.92(15) . . . . ?
C1 C2 C3 C6 -128.21(14) . . . . ?
C5 C2 C3 C4 -125.91(14) . . . . ?
C1 C2 C3 C4 -2.03(18) . . . . ?
C6 C3 C4 C22 70.57(16) . . . . ?
C2 C3 C4 C22 -56.03(17) . . . . ?
C6 C3 C4 C12 -173.60(13) . . . . ?
C2 C3 C4 C12 59.80(16) . . . . ?
C3 C2 C5 O2 -8.0(2) . . . . ?
C1 C2 C5 O2 -131.39(16) . . . . ?
C3 C2 C5 O1 173.84(15) . . . . ?
C1 C2 C5 O1 50.4(2) . . . . ?
C2 C3 C6 O3 -21.5(2) . . . . ?
C4 C3 C6 O3 -146.26(17) . . . . ?
C2 C3 C6 O4 160.65(15) . . . . ?
C4 C3 C6 O4 35.92(19) . . . . ?
C21 C1 C11 C16 133.14(18) . . . . ?
C2 C1 C11 C16 -114.12(19) . . . . ?
C21 C1 C11 C12 -52.33(19) . . . . ?
C2 C1 C11 C12 60.42(17) . . . . ?
C16 C11 C12 C13 0.8(3) . . . . ?
C1 C11 C12 C13 -174.18(16) . . . . ?
C16 C11 C12 C4 174.89(16) . . . . ?
C1 C11 C12 C4 0.0(2) . . . . ?
C22 C4 C12 C13 -133.53(18) . . . . ?
C3 C4 C12 C13 112.87(19) . . . . ?
C22 C4 C12 C11 52.72(19) . . . . ?
C3 C4 C12 C11 -60.89(18) . . . . ?
C11 C12 C13 C14 -0.9(3) . . . . ?
C4 C12 C13 C14 -174.21(17) . . . . ?
C12 C13 C14 C15 0.1(3) . . . . ?
C13 C14 C15 C16 0.8(3) . . . . ?
C12 C11 C16 C15 0.2(3) . . . . ?
C1 C11 C16 C15 174.39(17) . . . . ?
C14 C15 C16 C11 -1.0(3) . . . . ?
C11 C1 C21 C26 -131.10(18) . . . . ?
C2 C1 C21 C26 116.19(19) . . . . ?
C11 C1 C21 C22 52.47(19) . . . . ?
C2 C1 C21 C22 -60.25(17) . . . . ?
C26 C21 C22 C23 0.3(3) . . . . ?
C1 C21 C22 C23 176.98(15) . . . . ?
C26 C21 C22 C4 -176.63(16) . . . . ?
C1 C21 C22 C4 0.0(2) . . . . ?
C12 C4 C22 C23 130.53(18) . . . . ?
C3 C4 C22 C23 -117.18(18) . . . . ?
C12 C4 C22 C21 -52.75(18) . . . . ?
C3 C4 C22 C21 59.54(18) . . . . ?
C21 C22 C23 C24 0.7(3) . . . . ?
C4 C22 C23 C24 177.19(18) . . . . ?
C22 C23 C24 C25 -1.3(3) . . . . ?
C23 C24 C25 C26 0.8(3) . . . . ?
C22 C21 C26 C25 -0.8(3) . . . . ?
C1 C21 C26 C25 -176.98(17) . . . . ?
C24 C25 C26 C21 0.2(3) . . . . ?
C35 N3 C31 C32 -2.4(3) . . . . ?
C35 N3 C31 C36 178.6(2) . . . . ?
N3 C31 C32 C33 2.2(3) . . . . ?
C36 C31 C32 C33 -178.9(2) . . . . ?
C31 C32 C33 C34 -0.4(4) . . . . ?
C32 C33 C34 C35 -1.3(4) . . . . ?
C31 N3 C35 C34 0.7(3) . . . . ?
C33 C34 C35 N3 1.2(4) . . . . ?

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
_geom_hbond_publ_flag
N3 H3 O1 0.93(3) 2.49(3) 3.058(2) 120(2) 1_565 yes
N3 H3 O2 0.93(3) 1.74(3) 2.663(2) 179(3) 1_565 yes
O4 H4A O1 0.84 1.68 2.487(2) 159 2_664 yes
C1 H1 O3 1.00 2.56 3.542(2) 168 2_665 yes
C2 H2 O3 1.00 2.41 2.862(2) 107 . yes
C3 H3A O2 1.00 2.29 2.807(2) 111 . yes
C15 H15 O4 0.95 2.53 3.384(2) 149 4_645 yes
C35 H35 O1 0.95 2.45 3.062(2) 122 1_565 yes

_refine_diff_density_max         0.188
_refine_diff_density_min         -0.234
_refine_diff_density_rms         0.039


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: 2-methylpyridine'
####################################################################### 
# 
# 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_ma043
_database_code_depnum_ccdc_archive 'CCDC 2155877'
loop_
_audit_author_name
_audit_author_address
'Eric Hosten'
;Nelson Mandela University
South Africa
;
_audit_update_record             
;
2022-03-02 deposited with the CCDC.	2022-05-30 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            
'trans-9,10-dihydro-9,10-ethanoanthracene-11,12-dicarboxylic acid'
_chemical_melting_point          513.15
_chemical_formula_moiety         'C18 H13 O4, C6 H8 N'
_chemical_formula_sum            'C24 H21 N O4'
_chemical_formula_weight         387.42

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'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   8.8567(5)
_cell_length_b                   12.3590(7)
_cell_length_c                   18.2675(10)
_cell_angle_alpha                90
_cell_angle_beta                 100.800(2)
_cell_angle_gamma                90
_cell_volume                     1964.14(19)
_cell_formula_units_Z            4
_cell_measurement_temperature    200(2)
_cell_measurement_reflns_used    9207
_cell_measurement_theta_min      2.34
_cell_measurement_theta_max      28.27

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.310
_exptl_crystal_F_000             816
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.733
_exptl_crystal_size_mid          0.696
_exptl_crystal_size_min          0.467
_exptl_absorpt_coefficient_mu    0.089
_shelx_estimated_absorpt_T_min   0.937
_shelx_estimated_absorpt_T_max   0.959
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_correction_T_min  0.9420
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_process_details   'SADABS V2008/1 (Bruker AXS)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      200(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean 8.3333
_diffrn_reflns_number            37287
_diffrn_reflns_av_unetI/netI     0.0126
_diffrn_reflns_av_R_equivalents  0.0188
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         2.001
_diffrn_reflns_theta_max         28.306
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             4861
_reflns_number_gt                4133
_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       'Bruker Instrument Service v2011.4.0.0'
_computing_cell_refinement       'APEX2 v2011.4-1 (Bruker AXS)'
_computing_data_reduction        'SAINT V7.68A (Bruker AXS, 2009)'
_computing_structure_solution    'SHELXT-2018/2 (Sheldrick, 2015)'
_computing_structure_refinement  
'SHELXL-2018/3 (Sheldrick, 2015) and ShelXle (Hübschle, 2011)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 2012)'
_computing_publication_material  
'PLATON (Spek, 2009) and MERCURY (Macrae, 2008)'

_refine_special_details          
;
Carbon-bound H atoms were placed in calculated positions and were included in
the refinement in the riding model approximation, with Uiso(H) set to
1.2 Ueq(C).

The H atoms of the methyl group were allowed to rotate with a fixed angle around
the C---C bond to best fit the experimental electron density (HFIX 137 in the
SHELXL program (Sheldrick, 2015)), with Uiso(H) set to
1.5Ueq(C).

The H atom of the hydroxyl group was allowed to rotate with a fixed angle around
the C---O bonds to best fit the experimental electron density (HFIX 147 in the
SHELXL program (Sheldrick, 2015)), with Uiso(H) allowed to refine.

The nitrogen-bound H atom was located on a difference map and refined freely.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0543P)²+0.6057P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4861
_refine_ls_number_parameters     269
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0476
_refine_ls_R_factor_gt           0.0397
_refine_ls_wR_factor_ref         0.1110
_refine_ls_wR_factor_gt          0.1041
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_restrained_S_all      1.030
_refine_ls_shift/su_max          0.001
_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 0.11991(10) 0.28992(7) 0.83920(5) 0.0342(2) Uani 1 1 d . . . . .
H1A H 0.050082 0.248569 0.847884 0.056(5) Uiso 1 1 calc R . . . .
O2 O -0.07788(9) 0.39943(7) 0.79788(5) 0.0368(2) Uani 1 1 d . . . . .
O3 O 0.19093(12) 0.48983(8) 0.63410(5) 0.0431(2) Uani 1 1 d . . . . .
O4 O 0.05985(10) 0.64266(7) 0.62493(4) 0.0332(2) Uani 1 1 d . . . . .
N3 N 0.27682(13) 0.55201(9) 0.51453(6) 0.0369(2) Uani 1 1 d . . . . .
C1 C 0.30330(12) 0.48580(9) 0.85381(6) 0.0250(2) Uani 1 1 d . . . . .
H1 H 0.351120 0.420973 0.881697 0.030 Uiso 1 1 calc R U . . .
C2 C 0.17805(11) 0.45357(8) 0.78440(5) 0.0216(2) Uani 1 1 d . . . . .
H2 H 0.230256 0.412254 0.749177 0.026 Uiso 1 1 calc R U . . .
C3 C 0.10770(11) 0.55635(8) 0.74399(5) 0.0216(2) Uani 1 1 d . . . . .
H3 H -0.003776 0.558417 0.747138 0.026 Uiso 1 1 calc R U . . .
C4 C 0.18670(12) 0.65852(8) 0.78527(6) 0.0243(2) Uani 1 1 d . . . . .
H4 H 0.145105 0.727360 0.760638 0.029 Uiso 1 1 calc R U . . .
C5 C 0.05783(12) 0.38004(8) 0.80764(6) 0.0242(2) Uani 1 1 d . . . . .
C6 C 0.12006(12) 0.56334(8) 0.66186(6) 0.0248(2) Uani 1 1 d . . . . .
C11 C 0.22527(12) 0.55841(9) 0.90195(6) 0.0261(2) Uani 1 1 d . . . . .
C12 C 0.16057(12) 0.65076(9) 0.86456(6) 0.0256(2) Uani 1 1 d . . . . .
C13 C 0.07748(13) 0.72322(10) 0.89938(7) 0.0344(3) Uani 1 1 d . . . . .
H13 H 0.030236 0.784667 0.873412 0.041 Uiso 1 1 calc R U . . .
C14 C 0.06453(15) 0.70421(13) 0.97335(7) 0.0438(3) Uani 1 1 d . . . . .
H14 H 0.009151 0.753772 0.998066 0.053 Uiso 1 1 calc R U . . .
C15 C 0.13112(17) 0.61447(13) 1.01082(7) 0.0461(3) Uani 1 1 d . . . . .
H15 H 0.122867 0.603452 1.061384 0.055 Uiso 1 1 calc R U . . .
C16 C 0.21037(15) 0.53978(11) 0.97536(7) 0.0372(3) Uani 1 1 d . . . . .
H16 H 0.253737 0.476893 1.000929 0.045 Uiso 1 1 calc R U . . .
C21 C 0.41974(12) 0.55285(9) 0.82304(6) 0.0270(2) Uani 1 1 d . . . . .
C22 C 0.35660(13) 0.64560(9) 0.78585(6) 0.0268(2) Uani 1 1 d . . . . .
C23 C 0.44611(17) 0.71297(10) 0.75072(8) 0.0398(3) Uani 1 1 d . . . . .
H23 H 0.402470 0.774678 0.723739 0.048 Uiso 1 1 calc R U . . .
C24 C 0.60140(18) 0.68835(13) 0.75576(10) 0.0536(4) Uani 1 1 d . . . . .
H24 H 0.664336 0.734227 0.732451 0.064 Uiso 1 1 calc R U . . .
C25 C 0.66463(16) 0.59815(13) 0.79423(10) 0.0514(4) Uani 1 1 d . . . . .
H25 H 0.771104 0.583433 0.798056 0.062 Uiso 1 1 calc R U . . .
C26 C 0.57411(14) 0.52851(11) 0.82746(8) 0.0382(3) Uani 1 1 d . . . . .
H26 H 0.617246 0.465363 0.852763 0.046 Uiso 1 1 calc R U . . .
C31 C 0.45782(16) 0.65546(12) 0.46338(9) 0.0481(3) Uani 1 1 d . . . . .
C32 C 0.38682(17) 0.62704(11) 0.52186(8) 0.0445(3) Uani 1 1 d . . . . .
H32 H 0.417280 0.661987 0.568617 0.053 Uiso 1 1 calc R U . . .
C33 C 0.22793(15) 0.50286(12) 0.45000(7) 0.0398(3) Uani 1 1 d . . . . .
H33 H 0.147604 0.450973 0.445634 0.048 Uiso 1 1 calc R U . . .
C34 C 0.29298(17) 0.52672(13) 0.38956(7) 0.0473(3) Uani 1 1 d . . . . .
H34 H 0.258190 0.491705 0.343173 0.057 Uiso 1 1 calc R U . . .
C35 C 0.40904(17) 0.60182(14) 0.39682(8) 0.0499(4) Uani 1 1 d . . . . .
H35 H 0.456495 0.617123 0.355450 0.060 Uiso 1 1 calc R U . . .
C36 C 0.5813(3) 0.73982(18) 0.47236(15) 0.0907(8) Uani 1 1 d . . . . .
H36A H 0.654125 0.722682 0.439747 0.136 Uiso 1 1 calc R U . . .
H36B H 0.635472 0.741201 0.524301 0.136 Uiso 1 1 calc R U . . .
H36C H 0.534962 0.810809 0.458906 0.136 Uiso 1 1 calc R U . . .
H3A H 0.227(2) 0.5283(17) 0.5629(12) 0.080(6) Uiso 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C5 1.3253(13) . ?
O1 H1A 0.8400 . ?
O2 C5 1.2056(13) . ?
O3 C6 1.2633(13) . ?
O3 H3A 1.47(2) . ?
O4 C6 1.2512(13) . ?
N3 C33 1.3246(17) . ?
N3 C32 1.3335(19) . ?
N3 H3A 1.10(2) . ?
C1 C21 1.5111(15) . ?
C1 C11 1.5113(15) . ?
C1 C2 1.5716(14) . ?
C1 H1 1.0000 . ?
C2 C5 1.5196(14) . ?
C2 C3 1.5409(13) . ?
C2 H2 1.0000 . ?
C3 C6 1.5270(14) . ?
C3 C4 1.5668(14) . ?
C3 H3 1.0000 . ?
C4 C22 1.5113(15) . ?
C4 C12 1.5120(14) . ?
C4 H4 1.0000 . ?
C11 C16 1.3910(15) . ?
C11 C12 1.3968(16) . ?
C12 C13 1.3870(15) . ?
C13 C14 1.3972(18) . ?
C13 H13 0.9500 . ?
C14 C15 1.377(2) . ?
C14 H14 0.9500 . ?
C15 C16 1.391(2) . ?
C15 H15 0.9500 . ?
C16 H16 0.9500 . ?
C21 C26 1.3874(16) . ?
C21 C22 1.3949(16) . ?
C22 C23 1.3871(16) . ?
C23 C24 1.395(2) . ?
C23 H23 0.9500 . ?
C24 C25 1.379(3) . ?
C24 H24 0.9500 . ?
C25 C26 1.391(2) . ?
C25 H25 0.9500 . ?
C26 H26 0.9500 . ?
C31 C35 1.381(2) . ?
C31 C32 1.383(2) . ?
C31 C36 1.497(2) . ?
C32 H32 0.9500 . ?
C33 C34 1.370(2) . ?
C33 H33 0.9500 . ?
C34 C35 1.373(2) . ?
C34 H34 0.9500 . ?
C35 H35 0.9500 . ?
C36 H36A 0.9800 . ?
C36 H36B 0.9800 . ?
C36 H36C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C5 O1 H1A 109.5 . . ?
C6 O3 H3A 109.2(8) . . ?
C33 N3 C32 121.27(12) . . ?
C33 N3 H3A 118.7(11) . . ?
C32 N3 H3A 120.0(11) . . ?
C21 C1 C11 108.02(9) . . ?
C21 C1 C2 105.46(8) . . ?
C11 C1 C2 106.82(8) . . ?
C21 C1 H1 112.1 . . ?
C11 C1 H1 112.1 . . ?
C2 C1 H1 112.1 . . ?
C5 C2 C3 112.66(8) . . ?
C5 C2 C1 110.60(8) . . ?
C3 C2 C1 109.79(8) . . ?
C5 C2 H2 107.9 . . ?
C3 C2 H2 107.9 . . ?
C1 C2 H2 107.9 . . ?
C6 C3 C2 114.85(8) . . ?
C6 C3 C4 108.64(8) . . ?
C2 C3 C4 109.25(8) . . ?
C6 C3 H3 108.0 . . ?
C2 C3 H3 108.0 . . ?
C4 C3 H3 108.0 . . ?
C22 C4 C12 108.51(9) . . ?
C22 C4 C3 105.81(8) . . ?
C12 C4 C3 105.98(8) . . ?
C22 C4 H4 112.1 . . ?
C12 C4 H4 112.1 . . ?
C3 C4 H4 112.1 . . ?
O2 C5 O1 123.52(10) . . ?
O2 C5 C2 124.83(10) . . ?
O1 C5 C2 111.65(9) . . ?
O4 C6 O3 122.73(10) . . ?
O4 C6 C3 118.18(9) . . ?
O3 C6 C3 119.09(9) . . ?
C16 C11 C12 120.16(11) . . ?
C16 C11 C1 126.80(11) . . ?
C12 C11 C1 113.02(9) . . ?
C13 C12 C11 120.50(10) . . ?
C13 C12 C4 126.01(10) . . ?
C11 C12 C4 113.45(9) . . ?
C12 C13 C14 118.80(12) . . ?
C12 C13 H13 120.6 . . ?
C14 C13 H13 120.6 . . ?
C15 C14 C13 120.73(12) . . ?
C15 C14 H14 119.6 . . ?
C13 C14 H14 119.6 . . ?
C14 C15 C16 120.65(12) . . ?
C14 C15 H15 119.7 . . ?
C16 C15 H15 119.7 . . ?
C11 C16 C15 119.10(12) . . ?
C11 C16 H16 120.4 . . ?
C15 C16 H16 120.4 . . ?
C26 C21 C22 120.48(11) . . ?
C26 C21 C1 126.38(11) . . ?
C22 C21 C1 113.12(9) . . ?
C23 C22 C21 120.46(11) . . ?
C23 C22 C4 126.01(11) . . ?
C21 C22 C4 113.45(9) . . ?
C22 C23 C24 118.71(13) . . ?
C22 C23 H23 120.6 . . ?
C24 C23 H23 120.6 . . ?
C25 C24 C23 120.74(12) . . ?
C25 C24 H24 119.6 . . ?
C23 C24 H24 119.6 . . ?
C24 C25 C26 120.68(13) . . ?
C24 C25 H25 119.7 . . ?
C26 C25 H25 119.7 . . ?
C21 C26 C25 118.87(13) . . ?
C21 C26 H26 120.6 . . ?
C25 C26 H26 120.6 . . ?
C35 C31 C32 116.47(14) . . ?
C35 C31 C36 122.15(17) . . ?
C32 C31 C36 121.38(17) . . ?
N3 C32 C31 121.91(13) . . ?
N3 C32 H32 119.0 . . ?
C31 C32 H32 119.0 . . ?
N3 C33 C34 120.12(14) . . ?
N3 C33 H33 119.9 . . ?
C34 C33 H33 119.9 . . ?
C33 C34 C35 119.22(13) . . ?
C33 C34 H34 120.4 . . ?
C35 C34 H34 120.4 . . ?
C34 C35 C31 120.96(14) . . ?
C34 C35 H35 119.5 . . ?
C31 C35 H35 119.5 . . ?
C31 C36 H36A 109.5 . . ?
C31 C36 H36B 109.5 . . ?
H36A C36 H36B 109.5 . . ?
C31 C36 H36C 109.5 . . ?
H36A C36 H36C 109.5 . . ?
H36B C36 H36C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C21 C1 C2 C5 176.85(8) . . . . ?
C11 C1 C2 C5 -68.39(10) . . . . ?
C21 C1 C2 C3 -58.22(10) . . . . ?
C11 C1 C2 C3 56.54(10) . . . . ?
C5 C2 C3 C6 -113.16(10) . . . . ?
C1 C2 C3 C6 123.11(9) . . . . ?
C5 C2 C3 C4 124.51(9) . . . . ?
C1 C2 C3 C4 0.78(11) . . . . ?
C6 C3 C4 C22 -68.86(10) . . . . ?
C2 C3 C4 C22 57.13(10) . . . . ?
C6 C3 C4 C12 176.03(8) . . . . ?
C2 C3 C4 C12 -57.98(10) . . . . ?
C3 C2 C5 O2 -1.79(14) . . . . ?
C1 C2 C5 O2 121.49(11) . . . . ?
C3 C2 C5 O1 177.12(8) . . . . ?
C1 C2 C5 O1 -59.59(11) . . . . ?
C2 C3 C6 O4 177.21(9) . . . . ?
C4 C3 C6 O4 -60.13(12) . . . . ?
C2 C3 C6 O3 -3.25(14) . . . . ?
C4 C3 C6 O3 119.42(11) . . . . ?
C21 C1 C11 C16 -127.05(12) . . . . ?
C2 C1 C11 C16 119.93(12) . . . . ?
C21 C1 C11 C12 54.77(11) . . . . ?
C2 C1 C11 C12 -58.26(11) . . . . ?
C16 C11 C12 C13 -1.74(16) . . . . ?
C1 C11 C12 C13 176.58(10) . . . . ?
C16 C11 C12 C4 -179.78(10) . . . . ?
C1 C11 C12 C4 -1.46(13) . . . . ?
C22 C4 C12 C13 129.85(11) . . . . ?
C3 C4 C12 C13 -116.90(11) . . . . ?
C22 C4 C12 C11 -52.23(11) . . . . ?
C3 C4 C12 C11 61.02(11) . . . . ?
C11 C12 C13 C14 2.32(17) . . . . ?
C4 C12 C13 C14 -179.90(11) . . . . ?
C12 C13 C14 C15 -0.88(19) . . . . ?
C13 C14 C15 C16 -1.2(2) . . . . ?
C12 C11 C16 C15 -0.32(17) . . . . ?
C1 C11 C16 C15 -178.39(11) . . . . ?
C14 C15 C16 C11 1.8(2) . . . . ?
C11 C1 C21 C26 127.35(12) . . . . ?
C2 C1 C21 C26 -118.72(12) . . . . ?
C11 C1 C21 C22 -54.23(12) . . . . ?
C2 C1 C21 C22 59.70(11) . . . . ?
C26 C21 C22 C23 2.08(17) . . . . ?
C1 C21 C22 C23 -176.44(10) . . . . ?
C26 C21 C22 C4 178.99(10) . . . . ?
C1 C21 C22 C4 0.46(13) . . . . ?
C12 C4 C22 C23 -130.47(12) . . . . ?
C3 C4 C22 C23 116.17(12) . . . . ?
C12 C4 C22 C21 52.82(12) . . . . ?
C3 C4 C22 C21 -60.54(11) . . . . ?
C21 C22 C23 C24 -2.42(18) . . . . ?
C4 C22 C23 C24 -178.91(11) . . . . ?
C22 C23 C24 C25 0.7(2) . . . . ?
C23 C24 C25 C26 1.4(2) . . . . ?
C22 C21 C26 C25 0.02(18) . . . . ?
C1 C21 C26 C25 178.33(12) . . . . ?
C24 C25 C26 C21 -1.7(2) . . . . ?
C33 N3 C32 C31 -1.6(2) . . . . ?
C35 C31 C32 N3 -0.1(2) . . . . ?
C36 C31 C32 N3 -179.97(15) . . . . ?
C32 N3 C33 C34 1.6(2) . . . . ?
N3 C33 C34 C35 0.1(2) . . . . ?
C33 C34 C35 C31 -1.8(2) . . . . ?
C32 C31 C35 C34 1.8(2) . . . . ?
C36 C31 C35 C34 -178.37(16) . . . . ?

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
_geom_hbond_publ_flag
O1 H1A O4 0.84 1.76 2.5822(11) 167 2_546 yes
N3 H3A O3 1.10(2) 1.47(2) 2.5618(14) 168.9(19) . yes
N3 H3A O4 1.10(2) 2.47(2) 3.2353(13) 125.6(14) . yes
C2 H2 O3 1.00 2.28 2.8052(13) 112 . yes
C3 H3 O2 1.00 2.32 2.8351(13) 111 . yes
C4 H4 O2 1.00 2.40 3.3989(14) 173 2_556 yes
C33 H33 O4 0.95 2.34 3.2089(17) 151 3_566 yes

_refine_diff_density_max         0.345
_refine_diff_density_min         -0.207
_refine_diff_density_rms         0.038


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: 3-methylpyridine'
####################################################################### 
# 
# 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_ja216
_database_code_depnum_ccdc_archive 'CCDC 2144422'
loop_
_audit_author_name
_audit_author_address
'Eric C. Hosten'
;Nelson Mandela University
South Africa
;
_audit_update_record             
;
2022-01-25 deposited with the CCDC.	2022-05-30 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        
'trans-9,10-dihydro-9,10-ethanoanthracene-11,12-dicarboxylic acid'
_chemical_name_common            ?
_chemical_melting_point          513.15
_chemical_formula_moiety         'C18 H14 O4, 2(C5 H5 N)'
_chemical_formula_sum            'C28 H24 N2 O4'
_chemical_formula_weight         452.49

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'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'

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

_cell_length_a                   17.3469(10)
_cell_length_b                   11.0693(7)
_cell_length_c                   25.0564(14)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     4811.3(5)
_cell_formula_units_Z            8
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    9494
_cell_measurement_theta_min      2.33
_cell_measurement_theta_max      27.81

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.249
_exptl_crystal_F_000             1904
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.665
_exptl_crystal_size_mid          0.603
_exptl_crystal_size_min          0.284
_exptl_absorpt_coefficient_mu    0.084
_shelx_estimated_absorpt_T_min   0.946
_shelx_estimated_absorpt_T_max   0.976
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_correction_T_min  0.9456
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_process_details   'SADABS V2008/1 (Bruker AXS)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean 8.3333
_diffrn_reflns_number            84933
_diffrn_reflns_av_unetI/netI     0.0193
_diffrn_reflns_av_R_equivalents  0.0452
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         1.625
_diffrn_reflns_theta_max         28.378
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             6023
_reflns_number_gt                4598
_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       'Bruker Instrument Service v2011.4.0.0'
_computing_cell_refinement       'APEX2 v2011.4-1 (Bruker AXS)'
_computing_data_reduction        'SAINT V7.68A (Bruker AXS, 2009)'
_computing_structure_solution    'SHELXT-2018/2 (Sheldrick, 2015)'
_computing_structure_refinement  
'SHELXL-2018/3 (Sheldrick, 2015) and ShelXle (Hübschle, 2011)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 2012)'
_computing_publication_material  
'PLATON (Spek, 2009) and MERCURY (Macrae, 2008)'

_refine_special_details          
;
Carbon-bound H atoms were placed in calculated positions and were included in
the refinement in the riding model approximation, with Uiso(H) set to
1.2 Ueq(C).

The H atoms of the hydroxyl groups were allowed to rotate with a fixed angle
around the C---O bonds to best fit the experimental electron density (HFIX 147
in the SHELXL program (Sheldrick, 2015)), with Uiso(H) set to
1.5Ueq(O).
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0494P)²+2.3094P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_extinction_coef       0.0028(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         6023
_refine_ls_number_parameters     310
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0690
_refine_ls_R_factor_gt           0.0503
_refine_ls_wR_factor_ref         0.1375
_refine_ls_wR_factor_gt          0.1223
_refine_ls_goodness_of_fit_ref   1.023
_refine_ls_restrained_S_all      1.023
_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 0.54198(7) 0.43160(15) 0.89813(5) 0.0677(4) Uani 1 1 d . . . . .
O2 O 0.60482(7) 0.39908(16) 0.82330(5) 0.0701(4) Uani 1 1 d . . . . .
H2A H 0.641129 0.425496 0.840700 0.105 Uiso 1 1 calc R U . . .
O3 O 0.48825(10) 0.34406(12) 0.70974(5) 0.0724(4) Uani 1 1 d . . . . .
O4 O 0.52916(11) 0.15652(11) 0.71070(5) 0.0774(5) Uani 1 1 d . . . . .
H4A H 0.540094 0.172024 0.679602 0.116 Uiso 1 1 calc R U . . .
N3 N 0.73293(9) 0.48792(17) 0.86839(7) 0.0638(4) Uani 1 1 d . . . . .
N4 N 0.58611(11) 0.17430(14) 0.61181(6) 0.0625(4) Uani 1 1 d . . . . .
C1 C 0.40010(8) 0.34162(12) 0.85753(6) 0.0331(3) Uani 1 1 d . . . . .
H1 H 0.389928 0.414700 0.878449 0.040 Uiso 1 1 calc R U . . .
C2 C 0.47313(8) 0.35477(12) 0.82219(5) 0.0323(3) Uani 1 1 d . . . . .
H2 H 0.461699 0.415738 0.794961 0.039 Uiso 1 1 calc R U . . .
C3 C 0.48906(8) 0.23429(12) 0.79269(5) 0.0323(3) Uani 1 1 d . . . . .
H3 H 0.536434 0.199447 0.807423 0.039 Uiso 1 1 calc R U . . .
C4 C 0.42139(8) 0.14400(12) 0.80405(5) 0.0326(3) Uani 1 1 d . . . . .
H4 H 0.427558 0.067925 0.784506 0.039 Uiso 1 1 calc R U . . .
C5 C 0.54264(8) 0.39837(13) 0.85293(6) 0.0385(3) Uani 1 1 d . . . . .
C6 C 0.50083(8) 0.25228(13) 0.73344(6) 0.0388(3) Uani 1 1 d . . . . .
C11 C 0.40979(7) 0.23167(13) 0.89254(6) 0.0347(3) Uani 1 1 d . . . . .
C12 C 0.41977(8) 0.12470(13) 0.86377(6) 0.0342(3) Uani 1 1 d . . . . .
C13 C 0.42527(9) 0.01506(15) 0.89002(7) 0.0436(4) Uani 1 1 d . . . . .
H13 H 0.431415 -0.056309 0.870903 0.052 Uiso 1 1 calc R U . . .
C14 C 0.42148(10) 0.01333(18) 0.94546(7) 0.0560(5) Uani 1 1 d . . . . .
H14 H 0.424679 -0.059921 0.963505 0.067 Uiso 1 1 calc R U . . .
C15 C 0.41306(11) 0.11868(19) 0.97386(7) 0.0579(5) Uani 1 1 d . . . . .
H15 H 0.411388 0.116194 1.010941 0.069 Uiso 1 1 calc R U . . .
C16 C 0.40702(9) 0.22885(17) 0.94767(6) 0.0463(4) Uani 1 1 d . . . . .
H16 H 0.401175 0.299965 0.967016 0.056 Uiso 1 1 calc R U . . .
C21 C 0.33491(8) 0.31344(12) 0.81916(6) 0.0334(3) Uani 1 1 d . . . . .
C22 C 0.34705(8) 0.20764(12) 0.78977(5) 0.0329(3) Uani 1 1 d . . . . .
C23 C 0.29321(9) 0.16999(13) 0.75286(6) 0.0400(3) Uani 1 1 d . . . . .
H23 H 0.301733 0.100478 0.732866 0.048 Uiso 1 1 calc R U . . .
C24 C 0.22620(9) 0.23660(15) 0.74577(7) 0.0465(4) Uani 1 1 d . . . . .
H24 H 0.189426 0.211056 0.721231 0.056 Uiso 1 1 calc R U . . .
C25 C 0.21391(9) 0.34051(15) 0.77494(7) 0.0467(4) Uani 1 1 d . . . . .
H25 H 0.168737 0.384387 0.770052 0.056 Uiso 1 1 calc R U . . .
C26 C 0.26835(8) 0.38005(14) 0.81150(7) 0.0416(3) Uani 1 1 d . . . . .
H26 H 0.260182 0.450790 0.830708 0.050 Uiso 1 1 calc R U . . .
C31 C 0.80266(11) 0.4537(2) 0.85394(9) 0.0698(6) Uani 1 1 d . . . . .
H31 H 0.806861 0.389708 0.830085 0.084 Uiso 1 1 calc R U . . .
C32 C 0.86907(12) 0.5061(2) 0.87168(9) 0.0735(6) Uani 1 1 d . . . . .
H32 H 0.916781 0.478097 0.860115 0.088 Uiso 1 1 calc R U . . .
C33 C 0.86446(14) 0.5976(2) 0.90571(10) 0.0813(7) Uani 1 1 d . . . . .
H33 H 0.908845 0.634816 0.918492 0.098 Uiso 1 1 calc R U . . .
C34 C 0.79323(19) 0.6363(3) 0.92163(12) 0.1051(10) Uani 1 1 d . . . . .
H34 H 0.788271 0.700539 0.945284 0.126 Uiso 1 1 calc R U . . .
C35 C 0.72824(14) 0.5777(3) 0.90178(11) 0.0864(7) Uani 1 1 d . . . . .
H35 H 0.679775 0.603597 0.912781 0.104 Uiso 1 1 calc R U . . .
C41 C 0.66209(14) 0.16103(19) 0.61095(9) 0.0695(6) Uani 1 1 d . . . . .
H41 H 0.689423 0.172788 0.642455 0.083 Uiso 1 1 calc R U . . .
C42 C 0.70139(16) 0.1314(3) 0.56660(15) 0.0960(9) Uani 1 1 d . . . . .
H42 H 0.754660 0.122079 0.567498 0.115 Uiso 1 1 calc R U . . .
C43 C 0.6619(3) 0.1153(3) 0.52078(13) 0.1126(12) Uani 1 1 d . . . . .
H43 H 0.687742 0.094287 0.489622 0.135 Uiso 1 1 calc R U . . .
C44 C 0.5859(2) 0.1298(3) 0.52039(10) 0.1039(11) Uani 1 1 d . . . . .
H44 H 0.558185 0.120333 0.488887 0.125 Uiso 1 1 calc R U . . .
C45 C 0.54926(14) 0.1583(2) 0.56624(11) 0.0801(7) Uani 1 1 d . . . . .
H45 H 0.495939 0.166968 0.565708 0.096 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 C5 1.1909(19) . ?
O2 C5 1.3095(19) . ?
O2 H2A 0.8200 . ?
O3 C6 1.1968(19) . ?
O4 C6 1.2999(19) . ?
O4 H4A 0.8200 . ?
N3 C35 1.302(3) . ?
N3 C31 1.318(3) . ?
N4 C45 1.321(3) . ?
N4 C41 1.326(3) . ?
C1 C11 1.510(2) . ?
C1 C21 1.5165(19) . ?
C1 C2 1.5524(19) . ?
C1 H1 0.9800 . ?
C2 C5 1.5099(19) . ?
C2 C3 1.5496(18) . ?
C2 H2 0.9800 . ?
C3 C6 1.512(2) . ?
C3 C4 1.5679(18) . ?
C3 H3 0.9800 . ?
C4 C12 1.5117(19) . ?
C4 C22 1.5123(18) . ?
C4 H4 0.9800 . ?
C11 C16 1.383(2) . ?
C11 C12 1.397(2) . ?
C12 C13 1.384(2) . ?
C13 C14 1.391(2) . ?
C13 H13 0.9300 . ?
C14 C15 1.374(3) . ?
C14 H14 0.9300 . ?
C15 C16 1.389(3) . ?
C15 H15 0.9300 . ?
C16 H16 0.9300 . ?
C21 C26 1.3834(19) . ?
C21 C22 1.3993(19) . ?
C22 C23 1.379(2) . ?
C23 C24 1.388(2) . ?
C23 H23 0.9300 . ?
C24 C25 1.379(2) . ?
C24 H24 0.9300 . ?
C25 C26 1.387(2) . ?
C25 H25 0.9300 . ?
C26 H26 0.9300 . ?
C31 C32 1.364(3) . ?
C31 H31 0.9300 . ?
C32 C33 1.327(3) . ?
C32 H32 0.9300 . ?
C33 C34 1.367(4) . ?
C33 H33 0.9300 . ?
C34 C35 1.392(4) . ?
C34 H34 0.9300 . ?
C35 H35 0.9300 . ?
C41 C42 1.344(4) . ?
C41 H41 0.9300 . ?
C42 C43 1.349(5) . ?
C42 H42 0.9300 . ?
C43 C44 1.328(5) . ?
C43 H43 0.9300 . ?
C44 C45 1.350(4) . ?
C44 H44 0.9300 . ?
C45 H45 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
C5 O2 H2A 109.5 . . ?
C6 O4 H4A 109.5 . . ?
C35 N3 C31 116.94(18) . . ?
C45 N4 C41 116.88(19) . . ?
C11 C1 C21 106.59(11) . . ?
C11 C1 C2 108.43(11) . . ?
C21 C1 C2 105.44(11) . . ?
C11 C1 H1 112.0 . . ?
C21 C1 H1 112.0 . . ?
C2 C1 H1 112.0 . . ?
C5 C2 C3 112.09(11) . . ?
C5 C2 C1 113.00(12) . . ?
C3 C2 C1 109.69(10) . . ?
C5 C2 H2 107.3 . . ?
C3 C2 H2 107.2 . . ?
C1 C2 H2 107.3 . . ?
C6 C3 C2 112.29(11) . . ?
C6 C3 C4 111.31(11) . . ?
C2 C3 C4 109.17(10) . . ?
C6 C3 H3 108.0 . . ?
C2 C3 H3 108.0 . . ?
C4 C3 H3 108.0 . . ?
C12 C4 C22 106.50(11) . . ?
C12 C4 C3 106.49(11) . . ?
C22 C4 C3 107.37(10) . . ?
C12 C4 H4 112.0 . . ?
C22 C4 H4 112.0 . . ?
C3 C4 H4 112.0 . . ?
O1 C5 O2 123.05(14) . . ?
O1 C5 C2 125.17(14) . . ?
O2 C5 C2 111.75(13) . . ?
O3 C6 O4 122.93(14) . . ?
O3 C6 C3 125.06(14) . . ?
O4 C6 C3 111.98(13) . . ?
C16 C11 C12 120.05(14) . . ?
C16 C11 C1 126.52(14) . . ?
C12 C11 C1 113.39(12) . . ?
C13 C12 C11 120.43(13) . . ?
C13 C12 C4 126.38(13) . . ?
C11 C12 C4 113.16(12) . . ?
C12 C13 C14 118.92(16) . . ?
C12 C13 H13 120.5 . . ?
C14 C13 H13 120.5 . . ?
C15 C14 C13 120.70(16) . . ?
C15 C14 H14 119.6 . . ?
C13 C14 H14 119.6 . . ?
C14 C15 C16 120.58(16) . . ?
C14 C15 H15 119.7 . . ?
C16 C15 H15 119.7 . . ?
C11 C16 C15 119.29(16) . . ?
C11 C16 H16 120.4 . . ?
C15 C16 H16 120.4 . . ?
C26 C21 C22 119.91(13) . . ?
C26 C21 C1 126.92(13) . . ?
C22 C21 C1 113.17(11) . . ?
C23 C22 C21 120.26(13) . . ?
C23 C22 C4 126.54(13) . . ?
C21 C22 C4 113.19(12) . . ?
C22 C23 C24 119.51(14) . . ?
C22 C23 H23 120.2 . . ?
C24 C23 H23 120.2 . . ?
C25 C24 C23 120.30(14) . . ?
C25 C24 H24 119.8 . . ?
C23 C24 H24 119.8 . . ?
C24 C25 C26 120.53(14) . . ?
C24 C25 H25 119.7 . . ?
C26 C25 H25 119.7 . . ?
C21 C26 C25 119.47(14) . . ?
C21 C26 H26 120.3 . . ?
C25 C26 H26 120.3 . . ?
N3 C31 C32 124.3(2) . . ?
N3 C31 H31 117.8 . . ?
C32 C31 H31 117.8 . . ?
C33 C32 C31 118.9(2) . . ?
C33 C32 H32 120.6 . . ?
C31 C32 H32 120.6 . . ?
C32 C33 C34 118.8(2) . . ?
C32 C33 H33 120.6 . . ?
C34 C33 H33 120.6 . . ?
C33 C34 C35 118.8(2) . . ?
C33 C34 H34 120.6 . . ?
C35 C34 H34 120.6 . . ?
N3 C35 C34 122.3(2) . . ?
N3 C35 H35 118.8 . . ?
C34 C35 H35 118.8 . . ?
N4 C41 C42 123.0(2) . . ?
N4 C41 H41 118.5 . . ?
C42 C41 H41 118.5 . . ?
C41 C42 C43 118.6(3) . . ?
C41 C42 H42 120.7 . . ?
C43 C42 H42 120.7 . . ?
C44 C43 C42 119.7(3) . . ?
C44 C43 H43 120.2 . . ?
C42 C43 H43 120.2 . . ?
C43 C44 C45 119.3(3) . . ?
C43 C44 H44 120.4 . . ?
C45 C44 H44 120.4 . . ?
N4 C45 C44 122.6(3) . . ?
N4 C45 H45 118.7 . . ?
C44 C45 H45 118.7 . . ?

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
C11 C1 C2 C5 -73.28(14) . . . . ?
C21 C1 C2 C5 172.86(11) . . . . ?
C11 C1 C2 C3 52.57(14) . . . . ?
C21 C1 C2 C3 -61.28(13) . . . . ?
C5 C2 C3 C6 -104.06(14) . . . . ?
C1 C2 C3 C6 129.56(12) . . . . ?
C5 C2 C3 C4 132.00(12) . . . . ?
C1 C2 C3 C4 5.62(14) . . . . ?
C6 C3 C4 C12 175.06(11) . . . . ?
C2 C3 C4 C12 -60.42(13) . . . . ?
C6 C3 C4 C22 -71.17(14) . . . . ?
C2 C3 C4 C22 53.35(14) . . . . ?
C3 C2 C5 O1 -131.78(17) . . . . ?
C1 C2 C5 O1 -7.2(2) . . . . ?
C3 C2 C5 O2 50.14(17) . . . . ?
C1 C2 C5 O2 174.71(13) . . . . ?
C2 C3 C6 O3 -10.7(2) . . . . ?
C4 C3 C6 O3 112.02(18) . . . . ?
C2 C3 C6 O4 167.09(14) . . . . ?
C4 C3 C6 O4 -70.16(17) . . . . ?
C21 C1 C11 C16 -124.19(15) . . . . ?
C2 C1 C11 C16 122.72(15) . . . . ?
C21 C1 C11 C12 53.56(15) . . . . ?
C2 C1 C11 C12 -59.53(15) . . . . ?
C16 C11 C12 C13 1.4(2) . . . . ?
C1 C11 C12 C13 -176.51(12) . . . . ?
C16 C11 C12 C4 179.93(12) . . . . ?
C1 C11 C12 C4 2.02(16) . . . . ?
C22 C4 C12 C13 122.21(15) . . . . ?
C3 C4 C12 C13 -123.44(15) . . . . ?
C22 C4 C12 C11 -56.22(14) . . . . ?
C3 C4 C12 C11 58.13(14) . . . . ?
C11 C12 C13 C14 -0.6(2) . . . . ?
C4 C12 C13 C14 -178.95(14) . . . . ?
C12 C13 C14 C15 -0.5(3) . . . . ?
C13 C14 C15 C16 1.0(3) . . . . ?
C12 C11 C16 C15 -1.0(2) . . . . ?
C1 C11 C16 C15 176.63(14) . . . . ?
C14 C15 C16 C11 -0.2(3) . . . . ?
C11 C1 C21 C26 124.30(15) . . . . ?
C2 C1 C21 C26 -120.58(15) . . . . ?
C11 C1 C21 C22 -55.59(15) . . . . ?
C2 C1 C21 C22 59.54(14) . . . . ?
C26 C21 C22 C23 0.5(2) . . . . ?
C1 C21 C22 C23 -179.57(13) . . . . ?
C26 C21 C22 C4 -178.39(13) . . . . ?
C1 C21 C22 C4 1.50(16) . . . . ?
C12 C4 C22 C23 -124.78(15) . . . . ?
C3 C4 C22 C23 121.47(15) . . . . ?
C12 C4 C22 C21 54.06(14) . . . . ?
C3 C4 C22 C21 -59.69(14) . . . . ?
C21 C22 C23 C24 -1.2(2) . . . . ?
C4 C22 C23 C24 177.59(13) . . . . ?
C22 C23 C24 C25 0.8(2) . . . . ?
C23 C24 C25 C26 0.3(2) . . . . ?
C22 C21 C26 C25 0.5(2) . . . . ?
C1 C21 C26 C25 -179.35(14) . . . . ?
C24 C25 C26 C21 -0.9(2) . . . . ?
C35 N3 C31 C32 0.0(4) . . . . ?
N3 C31 C32 C33 0.0(4) . . . . ?
C31 C32 C33 C34 -0.2(4) . . . . ?
C32 C33 C34 C35 0.4(5) . . . . ?
C31 N3 C35 C34 0.2(4) . . . . ?
C33 C34 C35 N3 -0.4(5) . . . . ?
C45 N4 C41 C42 -0.7(3) . . . . ?
N4 C41 C42 C43 0.6(4) . . . . ?
C41 C42 C43 C44 0.4(5) . . . . ?
C42 C43 C44 C45 -1.1(5) . . . . ?
C41 N4 C45 C44 0.0(3) . . . . ?
C43 C44 C45 N4 1.0(4) . . . . ?

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
_geom_hbond_publ_flag
O2 H2A N3 0.82 1.87 2.6800(19) 170 . yes
O4 H4A N4 0.82 1.88 2.675(2) 164 . yes
C2 H2 O3 0.98 2.32 2.8322(19) 111 . yes
C25 H25 O2 0.93 2.59 3.172(2) 121 6_557 yes
C44 H44 O1 0.93 2.36 3.229(3) 155 7_565 yes

_refine_diff_density_max         0.264
_refine_diff_density_min         -0.285
_refine_diff_density_rms         0.037


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: pyridine'
