# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2023

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_2PYRIDsq
_database_code_depnum_ccdc_archive 'CCDC 2144345'
loop_
_audit_author_name
_audit_author_address
'Mino Caira'
;University of Cape Town
South Africa
;
_audit_update_record             
;
2023-01-12 deposited with the CCDC.	2023-02-28 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        
'dimethyl trans-9,10-dihydro-9,10-ethanoanthracene-11,12-dicarboxylate pyridine clathrate'
_chemical_name_common            none
_chemical_melting_point          'decomp. at 330 K'
_chemical_formula_moiety         'C20 H18 O4, 0.5(C5 H5 N)'
_chemical_formula_sum            'C22.50 H20.50 N0.50 O4'
_chemical_formula_weight         361.89

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           60
_space_group_name_H-M_alt        'P b c n'
_space_group_name_Hall           '-P 2n 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+1/2, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y, -z+1/2'
'-x, -y, -z'
'x-1/2, y-1/2, -z-1/2'
'-x-1/2, y-1/2, z'
'x, -y, z-1/2'

_cell_length_a                   21.0161(11)
_cell_length_b                   15.2805(6)
_cell_length_c                   11.3726(5)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3652.2(3)
_cell_formula_units_Z            8
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9991
_cell_measurement_theta_min      2.44
_cell_measurement_theta_max      28.29

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.316
_exptl_crystal_F_000             1528
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.340
_exptl_crystal_size_mid          0.270
_exptl_crystal_size_min          0.190
_exptl_absorpt_coefficient_mu    0.090
_shelx_estimated_absorpt_T_min   0.970
_shelx_estimated_absorpt_T_max   0.983
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.905
_exptl_absorpt_correction_T_max  0.983
_exptl_absorpt_process_details   
;
 SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
 J. Appl. Cryst. 48 (2015) 3-10
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed tube'
_diffrn_measurement_device_type  'Bruker D8 VENTURE SCXRD diffractometer'
_diffrn_measurement_method       'omega-and phi-scans, width 1.5 deg.'
_diffrn_detector_area_resol_mean n/a
_diffrn_reflns_number            56008
_diffrn_reflns_av_unetI/netI     0.0178
_diffrn_reflns_av_R_equivalents  0.0404
_diffrn_reflns_limit_h_min       -28
_diffrn_reflns_limit_h_max       27
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.434
_diffrn_reflns_theta_max         28.307
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measured_fraction_theta_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_point_group_measured_fraction_full 0.991
_reflns_number_total             4519
_reflns_number_gt                3989
_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.
 
 Structure factors included contributions from the .fab file.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Apex3 v2019.1-0, Bruker (2019).'
_computing_cell_refinement       
'SAINT V8.40A, Bruker AXS Inc.: Madison (WI), USA.'
_computing_data_reduction        
'SAINT V8.40A, Bruker AXS Inc.: Madison (WI), USA.'
_computing_structure_solution    'SHELXS-Version 2018/3 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    
'POV-Ray in interface X-Seed (LJ Barbour, 1999)'
_computing_publication_material  'PLATON (Spek, 1990)'
_refine_special_details          
;The pyridine guest molecules are located in channels and are severely disordered.
The PLATON SQUEEZE procedure (A.L. Spek, 2015) was applied. This yielded a guest
electron count corresponding to a 2:0.9 host-guest molar ratio, in very good 
agreement with the accurate estimate from the 1H NMR spectrum which indicated 
a 2:1 molar ratio. The SQUEEZE parameters are appended to this file.,SQUEEZE
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0463P)²+1.4753P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4519
_refine_ls_number_parameters     219
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0442
_refine_ls_R_factor_gt           0.0386
_refine_ls_wR_factor_ref         0.1024
_refine_ls_wR_factor_gt          0.0985
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_restrained_S_all      1.037
_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
C1 C 0.41418(5) 0.25167(7) 0.64462(11) 0.0259(2) Uani 1 1 d . . . . .
H1 H 0.417205 0.227386 0.721313 0.031 Uiso 1 1 calc R U . . .
C2 C 0.46031(6) 0.23305(9) 0.56014(12) 0.0333(3) Uani 1 1 d . . . . .
H2 H 0.494592 0.195002 0.578898 0.040 Uiso 1 1 calc R U . . .
C3 C 0.45641(6) 0.26967(9) 0.44922(12) 0.0334(3) Uani 1 1 d . . . . .
H3 H 0.488411 0.257041 0.392706 0.040 Uiso 1 1 calc R U . . .
C4 C 0.40612(5) 0.32495(7) 0.41913(10) 0.0250(2) Uani 1 1 d . . . . .
H4 H 0.403815 0.350103 0.342861 0.030 Uiso 1 1 calc R U . . .
C5 C 0.19040(5) 0.32642(7) 0.44925(9) 0.0206(2) Uani 1 1 d . . . . .
H5 H 0.186505 0.351708 0.373283 0.025 Uiso 1 1 calc R U . . .
C6 C 0.14264(5) 0.27204(7) 0.49363(10) 0.0237(2) Uani 1 1 d . . . . .
H6 H 0.106202 0.259716 0.447047 0.028 Uiso 1 1 calc R U . . .
C7 C 0.14796(5) 0.23583(7) 0.60527(10) 0.0242(2) Uani 1 1 d . . . . .
H7 H 0.115502 0.198188 0.633954 0.029 Uiso 1 1 calc R U . . .
C8 C 0.20072(5) 0.25445(7) 0.67553(9) 0.0212(2) Uani 1 1 d . . . . .
H8 H 0.203986 0.230546 0.752408 0.025 Uiso 1 1 calc R U . . .
C9 C 0.30044(5) 0.39820(6) 0.48406(9) 0.0178(2) Uani 1 1 d . . . . .
H9 H 0.297177 0.420585 0.401653 0.021 Uiso 1 1 calc R U . . .
C10 C 0.30259(5) 0.47431(6) 0.57635(9) 0.0179(2) Uani 1 1 d . . . . .
H10 H 0.339784 0.512625 0.557448 0.021 Uiso 1 1 calc R U . . .
C11 C 0.31273(5) 0.43558(6) 0.70014(8) 0.0178(2) Uani 1 1 d . . . . .
H11 H 0.277979 0.457096 0.752797 0.021 Uiso 1 1 calc R U . . .
C12 C 0.30933(5) 0.33300(7) 0.69448(9) 0.0188(2) Uani 1 1 d . . . . .
H12 H 0.312417 0.305660 0.774164 0.023 Uiso 1 1 calc R U . . .
C13 C 0.24273(5) 0.52955(7) 0.57045(9) 0.0209(2) Uani 1 1 d . . . . .
O14 O 0.21110(5) 0.55263(6) 0.65299(7) 0.0365(2) Uani 1 1 d . . . . .
O15 O 0.22966(4) 0.55128(5) 0.45894(7) 0.02418(17) Uani 1 1 d . . . . .
C16 C 0.17326(6) 0.60345(9) 0.44095(11) 0.0362(3) Uani 1 1 d . . . . .
H16A H 0.136176 0.572276 0.472157 0.054 Uiso 1 1 calc R U . . .
H16B H 0.167359 0.613976 0.356651 0.054 Uiso 1 1 calc R U . . .
H16C H 0.177952 0.659543 0.481831 0.054 Uiso 1 1 calc R U . . .
C17 C 0.37628(5) 0.46410(6) 0.75101(9) 0.0187(2) Uani 1 1 d . . . . .
O18 O 0.41174(4) 0.51719(5) 0.70756(7) 0.02753(19) Uani 1 1 d . . . . .
O19 O 0.38801(3) 0.42326(5) 0.85278(6) 0.02263(17) Uani 1 1 d . . . . .
C20 C 0.44872(5) 0.44232(8) 0.90745(10) 0.0246(2) Uani 1 1 d . . . . .
H20A H 0.482817 0.413516 0.863209 0.037 Uiso 1 1 calc R U . . .
H20B H 0.448584 0.420631 0.988541 0.037 Uiso 1 1 calc R U . . .
H20C H 0.455816 0.505707 0.907572 0.037 Uiso 1 1 calc R U . . .
C1A C 0.36382(5) 0.30609(7) 0.61527(9) 0.0195(2) Uani 1 1 d . . . . .
C4A C 0.35947(5) 0.34264(6) 0.50235(9) 0.0192(2) Uani 1 1 d . . . . .
C5A C 0.24357(5) 0.34284(6) 0.51801(9) 0.0178(2) Uani 1 1 d . . . . .
C8A C 0.24832(5) 0.30824(6) 0.63183(9) 0.0181(2) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C1A 1.3867(14) . ?
C1 C2 1.3943(17) . ?
C1 H1 0.9500 . ?
C2 C3 1.3825(19) . ?
C2 H2 0.9500 . ?
C3 C4 1.3956(17) . ?
C3 H3 0.9500 . ?
C4 C4A 1.3891(14) . ?
C4 H4 0.9500 . ?
C5 C5A 1.3869(14) . ?
C5 C6 1.3973(15) . ?
C5 H5 0.9500 . ?
C6 C7 1.3894(16) . ?
C6 H6 0.9500 . ?
C7 C8 1.3962(15) . ?
C7 H7 0.9500 . ?
C8 C8A 1.3869(14) . ?
C8 H8 0.9500 . ?
C9 C5A 1.5143(13) . ?
C9 C4A 1.5177(14) . ?
C9 C10 1.5672(14) . ?
C9 H9 1.0000 . ?
C10 C13 1.5165(14) . ?
C10 C11 1.5420(14) . ?
C10 H10 1.0000 . ?
C11 C17 1.5194(14) . ?
C11 C12 1.5704(14) . ?
C11 H11 1.0000 . ?
C12 C1A 1.5138(14) . ?
C12 C8A 1.5148(13) . ?
C12 H12 1.0000 . ?
C13 O14 1.2030(13) . ?
C13 O15 1.3394(13) . ?
O15 C16 1.4429(14) . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C17 O18 1.2073(13) . ?
C17 O19 1.3377(13) . ?
O19 C20 1.4488(12) . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
C1A C4A 1.4034(14) . ?
C5A C8A 1.4018(14) . ?

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 C1 C2 119.16(11) . . ?
C1A C1 H1 120.4 . . ?
C2 C1 H1 120.4 . . ?
C3 C2 C1 120.33(11) . . ?
C3 C2 H2 119.8 . . ?
C1 C2 H2 119.8 . . ?
C2 C3 C4 120.90(11) . . ?
C2 C3 H3 119.5 . . ?
C4 C3 H3 119.5 . . ?
C4A C4 C3 119.03(11) . . ?
C4A C4 H4 120.5 . . ?
C3 C4 H4 120.5 . . ?
C5A C5 C6 118.87(10) . . ?
C5A C5 H5 120.6 . . ?
C6 C5 H5 120.6 . . ?
C7 C6 C5 120.60(10) . . ?
C7 C6 H6 119.7 . . ?
C5 C6 H6 119.7 . . ?
C6 C7 C8 120.38(10) . . ?
C6 C7 H7 119.8 . . ?
C8 C7 H7 119.8 . . ?
C8A C8 C7 119.25(10) . . ?
C8A C8 H8 120.4 . . ?
C7 C8 H8 120.4 . . ?
C5A C9 C4A 107.32(8) . . ?
C5A C9 C10 105.46(8) . . ?
C4A C9 C10 107.45(8) . . ?
C5A C9 H9 112.1 . . ?
C4A C9 H9 112.1 . . ?
C10 C9 H9 112.1 . . ?
C13 C10 C11 111.63(8) . . ?
C13 C10 C9 111.07(8) . . ?
C11 C10 C9 109.31(8) . . ?
C13 C10 H10 108.2 . . ?
C11 C10 H10 108.2 . . ?
C9 C10 H10 108.2 . . ?
C17 C11 C10 111.04(8) . . ?
C17 C11 C12 109.99(8) . . ?
C10 C11 C12 109.84(8) . . ?
C17 C11 H11 108.6 . . ?
C10 C11 H11 108.6 . . ?
C12 C11 H11 108.6 . . ?
C1A C12 C8A 107.01(8) . . ?
C1A C12 C11 105.14(8) . . ?
C8A C12 C11 107.88(8) . . ?
C1A C12 H12 112.1 . . ?
C8A C12 H12 112.1 . . ?
C11 C12 H12 112.1 . . ?
O14 C13 O15 123.56(10) . . ?
O14 C13 C10 125.95(10) . . ?
O15 C13 C10 110.49(8) . . ?
C13 O15 C16 116.08(9) . . ?
O15 C16 H16A 109.5 . . ?
O15 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
O15 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
O18 C17 O19 123.63(9) . . ?
O18 C17 C11 125.41(10) . . ?
O19 C17 C11 110.96(8) . . ?
C17 O19 C20 116.09(8) . . ?
O19 C20 H20A 109.5 . . ?
O19 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
O19 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C1 C1A C4A 120.57(10) . . ?
C1 C1A C12 126.65(10) . . ?
C4A C1A C12 112.78(9) . . ?
C4 C4A C1A 120.00(10) . . ?
C4 C4A C9 126.32(10) . . ?
C1A C4A C9 113.66(9) . . ?
C5 C5A C8A 120.65(9) . . ?
C5 C5A C9 126.40(9) . . ?
C8A C5A C9 112.95(9) . . ?
C8 C8A C5A 120.21(9) . . ?
C8 C8A C12 126.15(9) . . ?
C5A C8A C12 113.60(9) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C1A C1 C2 C3 1.13(18) . . . . ?
C1 C2 C3 C4 -0.75(19) . . . . ?
C2 C3 C4 C4A -0.27(18) . . . . ?
C5A C5 C6 C7 0.74(16) . . . . ?
C5 C6 C7 C8 1.03(17) . . . . ?
C6 C7 C8 C8A -1.15(16) . . . . ?
C5A C9 C10 C13 -61.56(10) . . . . ?
C4A C9 C10 C13 -175.81(8) . . . . ?
C5A C9 C10 C11 62.05(10) . . . . ?
C4A C9 C10 C11 -52.19(10) . . . . ?
C13 C10 C11 C17 -121.56(9) . . . . ?
C9 C10 C11 C17 115.16(9) . . . . ?
C13 C10 C11 C12 116.56(9) . . . . ?
C9 C10 C11 C12 -6.72(11) . . . . ?
C17 C11 C12 C1A -60.28(10) . . . . ?
C10 C11 C12 C1A 62.22(10) . . . . ?
C17 C11 C12 C8A -174.22(8) . . . . ?
C10 C11 C12 C8A -51.71(10) . . . . ?
C11 C10 C13 O14 10.51(15) . . . . ?
C9 C10 C13 O14 132.78(12) . . . . ?
C11 C10 C13 O15 -170.54(8) . . . . ?
C9 C10 C13 O15 -48.26(11) . . . . ?
O14 C13 O15 C16 -1.55(17) . . . . ?
C10 C13 O15 C16 179.46(9) . . . . ?
C10 C11 C17 O18 7.38(14) . . . . ?
C12 C11 C17 O18 129.17(11) . . . . ?
C10 C11 C17 O19 -173.49(8) . . . . ?
C12 C11 C17 O19 -51.70(11) . . . . ?
O18 C17 O19 C20 -3.41(14) . . . . ?
C11 C17 O19 C20 177.44(8) . . . . ?
C2 C1 C1A C4A -0.51(16) . . . . ?
C2 C1 C1A C12 179.51(10) . . . . ?
C8A C12 C1A C1 -124.52(11) . . . . ?
C11 C12 C1A C1 120.93(11) . . . . ?
C8A C12 C1A C4A 55.50(11) . . . . ?
C11 C12 C1A C4A -59.04(10) . . . . ?
C3 C4 C4A C1A 0.88(15) . . . . ?
C3 C4 C4A C9 -177.65(10) . . . . ?
C1 C1A C4A C4 -0.50(15) . . . . ?
C12 C1A C4A C4 179.48(9) . . . . ?
C1 C1A C4A C9 178.21(9) . . . . ?
C12 C1A C4A C9 -1.81(12) . . . . ?
C5A C9 C4A C4 125.40(10) . . . . ?
C10 C9 C4A C4 -121.60(11) . . . . ?
C5A C9 C4A C1A -53.21(11) . . . . ?
C10 C9 C4A C1A 59.79(10) . . . . ?
C6 C5 C5A C8A -2.39(15) . . . . ?
C6 C5 C5A C9 178.67(9) . . . . ?
C4A C9 C5A C5 -126.60(10) . . . . ?
C10 C9 C5A C5 119.07(11) . . . . ?
C4A C9 C5A C8A 54.39(11) . . . . ?
C10 C9 C5A C8A -59.94(10) . . . . ?
C7 C8 C8A C5A -0.50(15) . . . . ?
C7 C8 C8A C12 -178.17(10) . . . . ?
C5 C5A C8A C8 2.29(15) . . . . ?
C9 C5A C8A C8 -178.63(9) . . . . ?
C5 C5A C8A C12 -179.75(9) . . . . ?
C9 C5A C8A C12 -0.68(12) . . . . ?
C1A C12 C8A C8 123.42(11) . . . . ?
C11 C12 C8A C8 -123.89(11) . . . . ?
C1A C12 C8A C5A -54.38(11) . . . . ?
C11 C12 C8A C5A 58.30(11) . . . . ?

_refine_diff_density_max         0.321
_refine_diff_density_min         -0.159
_refine_diff_density_rms         0.038



_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: pyridine'
####################################################################### 
# 
# 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_ma147
_database_code_depnum_ccdc_archive 'CCDC 2236047'
loop_
_audit_author_name
_audit_author_address
'Eric Hosten'
;Nelson Mandela University
South Africa
;
_audit_update_record             
;
2023-01-13 deposited with the CCDC.	2023-02-28 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        
'trans-dimethyl 9,10-dihydro-9,10- ethanoanthracene-11,12-dicarboxylate'
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C20 H18 O4, 0.333(C6 H7 N)'
_chemical_formula_sum            'C22 H20.333 N0.333 O4'
_chemical_formula_weight         353.38

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           60
_space_group_name_H-M_alt        'P b c n'
_space_group_name_Hall           '-P 2n 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+1/2, z+1/2'
'-x, y, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y-1/2, -z-1/2'
'x, -y, z-1/2'
'-x-1/2, y-1/2, z'

_cell_length_a                   21.2925(13)
_cell_length_b                   15.5355(10)
_cell_length_c                   11.4506(6)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3787.7(4)
_cell_formula_units_Z            8
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    9745
_cell_measurement_theta_min      2.41
_cell_measurement_theta_max      28.07

_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             1493
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.869
_exptl_crystal_size_mid          0.536
_exptl_crystal_size_min          0.314
_exptl_absorpt_coefficient_mu    0.085
_shelx_estimated_absorpt_T_min   0.930
_shelx_estimated_absorpt_T_max   0.974
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_correction_T_min  0.9132
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_process_details   'SADABS-2008/1 (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            49829
_diffrn_reflns_av_unetI/netI     0.0216
_diffrn_reflns_av_R_equivalents  0.0392
_diffrn_reflns_limit_h_min       -28
_diffrn_reflns_limit_h_max       28
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         1.623
_diffrn_reflns_theta_max         28.360
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.997
_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             4730
_reflns_number_gt                3458
_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 non-disordered 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
1.5 Ueq(C). The H atoms of the disordered methyl groups were placed in
calculated positions (HFIX 33).

The 4-methylpyridine solvent/guest molecule is extensively disordered around a
2-fold rotational axis and inversion point. Residual electron density indicates
that the solvent has additional disorder orientations but attempts to include
them were unsuccessful. The disorder necessitated the use of various restraints
and constraints: RIGU, SIMU, ISOR, FLAT, SADI and DFIX. The benzene ring was was
forced into a regular hexagon with bond lengths 1.39 Å (AFIX 66 in the SHELXL
program (Sheldrick, 2015)).

A reflection with large difference between its observed and calculated
intensities was omitted. This is due to obstruction by the beam stop.,Solvent disorder
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0918P)²+1.6547P] 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     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4730
_refine_ls_number_parameters     271
_refine_ls_number_restraints     135
_refine_ls_R_factor_all          0.0850
_refine_ls_R_factor_gt           0.0601
_refine_ls_wR_factor_ref         0.1974
_refine_ls_wR_factor_gt          0.1645
_refine_ls_goodness_of_fit_ref   1.073
_refine_ls_restrained_S_all      1.077
_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 0.60946(7) 0.41631(10) 0.15033(12) 0.0586(4) Uani 1 1 d . . . . .
O2 O 0.58843(8) 0.51357(12) 0.28682(15) 0.0731(5) Uani 1 1 d . . . . .
O3 O 0.76239(7) 0.55199(9) 0.53666(12) 0.0591(4) Uani 1 1 d . . . . .
O4 O 0.77939(10) 0.55233(13) 0.34544(15) 0.0875(6) Uani 1 1 d . . . . .
C1 C 0.68788(8) 0.33036(12) 0.30968(15) 0.0437(4) Uani 1 1 d . . . . .
H1 H 0.684904 0.302889 0.232831 0.052 Uiso 1 1 calc R U . . .
C2 C 0.68390(8) 0.43055(12) 0.30153(14) 0.0416(4) Uani 1 1 d . . . . .
H2 H 0.717971 0.450729 0.250922 0.050 Uiso 1 1 calc R U . . .
C3 C 0.62196(9) 0.45860(12) 0.24827(15) 0.0451(4) Uani 1 1 d . . . . .
C4 C 0.55106(10) 0.43649(17) 0.0922(2) 0.0635(6) Uani 1 1 d . . . . .
H4A H 0.544854 0.497701 0.092146 0.095 Uiso 1 1 calc R U . . .
H4B H 0.516933 0.409210 0.132564 0.095 Uiso 1 1 calc R U . . .
H4C H 0.552579 0.415981 0.013125 0.095 Uiso 1 1 calc R U . . .
C5 C 0.69300(8) 0.47042(11) 0.42334(14) 0.0400(4) Uani 1 1 d . . . . .
H5 H 0.655905 0.505497 0.440723 0.048 Uiso 1 1 calc R U . . .
C6 C 0.74975(9) 0.52842(12) 0.42798(16) 0.0481(4) Uani 1 1 d . . . . .
C7 C 0.81271(14) 0.61191(18) 0.5532(3) 0.0851(9) Uani 1 1 d . . . . .
H7A H 0.819653 0.620331 0.635272 0.128 Uiso 1 1 calc R U . . .
H7B H 0.801978 0.665884 0.517613 0.128 Uiso 1 1 calc R U . . .
H7C H 0.850247 0.589687 0.517890 0.128 Uiso 1 1 calc R U . . .
C8 C 0.69665(8) 0.39709(11) 0.51661(14) 0.0399(4) Uani 1 1 d . . . . .
H8 H 0.699752 0.419854 0.596220 0.048 Uiso 1 1 calc R U . . .
C11 C 0.63511(8) 0.30346(11) 0.38975(16) 0.0454(4) Uani 1 1 d . . . . .
C12 C 0.63928(8) 0.34041(11) 0.50067(15) 0.0432(4) Uani 1 1 d . . . . .
C13 C 0.59440(9) 0.32161(14) 0.58422(19) 0.0545(5) Uani 1 1 d . . . . .
H13 H 0.596367 0.346695 0.657880 0.065 Uiso 1 1 calc R U . . .
C14 C 0.54633(10) 0.26467(16) 0.5564(3) 0.0687(6) Uani 1 1 d . . . . .
H14 H 0.516377 0.251080 0.612550 0.082 Uiso 1 1 calc R U . . .
C15 C 0.54227(11) 0.22802(16) 0.4472(3) 0.0714(7) Uani 1 1 d . . . . .
H15 H 0.509800 0.189987 0.430243 0.086 Uiso 1 1 calc R U . . .
C16 C 0.58632(10) 0.24764(14) 0.3629(2) 0.0592(5) Uani 1 1 d . . . . .
H16 H 0.583324 0.223649 0.288748 0.071 Uiso 1 1 calc R U . . .
C21 C 0.74873(8) 0.30825(11) 0.37167(15) 0.0427(4) Uani 1 1 d . . . . .
C22 C 0.75336(8) 0.34367(11) 0.48373(15) 0.0404(4) Uani 1 1 d . . . . .
C23 C 0.80593(9) 0.32891(13) 0.55151(17) 0.0499(4) Uani 1 1 d . . . . .
H23 H 0.809584 0.353665 0.625142 0.060 Uiso 1 1 calc R U . . .
C24 C 0.85313(10) 0.27662(16) 0.50794(19) 0.0621(6) Uani 1 1 d . . . . .
H24 H 0.888477 0.265706 0.553299 0.075 Uiso 1 1 calc R U . . .
C25 C 0.84846(10) 0.24047(16) 0.3982(2) 0.0645(6) Uani 1 1 d . . . . .
H25 H 0.880397 0.205113 0.370501 0.077 Uiso 1 1 calc R U . . .
C26 C 0.79641(10) 0.25666(14) 0.32918(18) 0.0549(5) Uani 1 1 d . . . . .
H26 H 0.793543 0.232983 0.254774 0.066 Uiso 1 1 calc R U . . .
N3 N 0.5139(9) 0.9930(10) 0.4481(15) 0.220(8) Uani 0.3333 1 d G U P A -1
C31 C 0.4530(8) 1.0159(8) 0.4172(17) 0.210(8) Uani 0.3333 1 d G U P A -1
H31 H 0.424917 1.034211 0.474154 0.252 Uiso 0.3333 1 calc R U P A -1
C32 C 0.4341(6) 1.0112(9) 0.3012(18) 0.232(8) Uani 0.3333 1 d DG U P A -1
H32 H 0.393384 1.026515 0.280497 0.278 Uiso 0.3333 1 calc R U P A -1
C33 C 0.4761(7) 0.9838(10) 0.2160(15) 0.235(8) Uani 0.3333 1 d DG U P A -1
C34 C 0.5370(7) 0.9610(10) 0.2469(15) 0.239(9) Uani 0.3333 1 d DG U P A -1
H34 H 0.565135 0.942636 0.189932 0.286 Uiso 0.3333 1 calc R U P A -1
C35 C 0.5559(7) 0.9656(11) 0.3629(16) 0.243(10) Uani 0.3333 1 d G U P A -1
H35 H 0.596669 0.950332 0.383589 0.291 Uiso 0.3333 1 calc R U P A -1
C36 C 0.4544(9) 0.9719(14) 0.082(2) 0.207(8) Uani 0.3333 1 d D U P A -1
H36A H 0.489438 0.952705 0.036389 0.311 Uiso 0.3333 1 calc R U P A -1
H36B H 0.421347 0.929986 0.078366 0.311 Uiso 0.3333 1 calc R U P A -1
H36C H 0.439494 1.025897 0.052440 0.311 Uiso 0.3333 1 calc R U P A -1


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C3 1.327(2) . ?
O1 C4 1.445(2) . ?
O2 C3 1.197(2) . ?
O3 C6 1.325(2) . ?
O3 C7 1.432(3) . ?
O4 C6 1.196(2) . ?
C1 C11 1.509(3) . ?
C1 C21 1.517(2) . ?
C1 C2 1.562(3) . ?
C1 H1 0.9800 . ?
C2 C3 1.517(2) . ?
C2 C5 1.538(2) . ?
C2 H2 0.9800 . ?
C4 H4A 0.9600 . ?
C4 H4B 0.9600 . ?
C4 H4C 0.9600 . ?
C5 C6 1.508(3) . ?
C5 C8 1.564(2) . ?
C5 H5 0.9800 . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
C8 C22 1.513(2) . ?
C8 C12 1.517(2) . ?
C8 H8 0.9800 . ?
C11 C16 1.388(3) . ?
C11 C12 1.397(3) . ?
C12 C13 1.383(3) . ?
C13 C14 1.390(3) . ?
C13 H13 0.9300 . ?
C14 C15 1.376(4) . ?
C14 H14 0.9300 . ?
C15 C16 1.380(3) . ?
C15 H15 0.9300 . ?
C16 H16 0.9300 . ?
C21 C26 1.382(3) . ?
C21 C22 1.400(2) . ?
C22 C23 1.381(2) . ?
C23 C24 1.385(3) . ?
C23 H23 0.9300 . ?
C24 C25 1.380(3) . ?
C24 H24 0.9300 . ?
C25 C26 1.384(3) . ?
C25 H25 0.9300 . ?
C26 H26 0.9300 . ?
N3 C31 1.3900 . ?
N3 C35 1.3900 . ?
C31 C32 1.3900 . ?
C31 H31 0.9300 . ?
C32 C33 1.3900 . ?
C32 H32 0.9300 . ?
C33 C34 1.3900 . ?
C33 C36 1.610(17) . ?
C34 C35 1.3900 . ?
C34 H34 0.9300 . ?
C35 H35 0.9300 . ?
C36 H36A 0.9600 . ?
C36 H36B 0.9600 . ?
C36 H36C 0.9600 . ?

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
C3 O1 C4 117.04(17) . . ?
C6 O3 C7 117.14(17) . . ?
C11 C1 C21 106.80(14) . . ?
C11 C1 C2 105.78(14) . . ?
C21 C1 C2 107.46(14) . . ?
C11 C1 H1 112.1 . . ?
C21 C1 H1 112.1 . . ?
C2 C1 H1 112.1 . . ?
C3 C2 C5 111.00(14) . . ?
C3 C2 C1 110.94(15) . . ?
C5 C2 C1 109.90(13) . . ?
C3 C2 H2 108.3 . . ?
C5 C2 H2 108.3 . . ?
C1 C2 H2 108.3 . . ?
O2 C3 O1 123.05(17) . . ?
O2 C3 C2 125.10(18) . . ?
O1 C3 C2 111.84(15) . . ?
O1 C4 H4A 109.5 . . ?
O1 C4 H4B 109.5 . . ?
H4A C4 H4B 109.5 . . ?
O1 C4 H4C 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
C6 C5 C2 111.93(14) . . ?
C6 C5 C8 111.81(14) . . ?
C2 C5 C8 109.40(14) . . ?
C6 C5 H5 107.8 . . ?
C2 C5 H5 107.8 . . ?
C8 C5 H5 107.8 . . ?
O4 C6 O3 123.32(19) . . ?
O4 C6 C5 125.50(18) . . ?
O3 C6 C5 111.16(15) . . ?
O3 C7 H7A 109.5 . . ?
O3 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
O3 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C22 C8 C12 107.12(14) . . ?
C22 C8 C5 105.63(13) . . ?
C12 C8 C5 107.50(14) . . ?
C22 C8 H8 112.1 . . ?
C12 C8 H8 112.1 . . ?
C5 C8 H8 112.1 . . ?
C16 C11 C12 120.37(18) . . ?
C16 C11 C1 126.59(18) . . ?
C12 C11 C1 113.04(15) . . ?
C13 C12 C11 119.89(18) . . ?
C13 C12 C8 126.55(17) . . ?
C11 C12 C8 113.53(15) . . ?
C12 C13 C14 119.0(2) . . ?
C12 C13 H13 120.5 . . ?
C14 C13 H13 120.5 . . ?
C15 C14 C13 121.2(2) . . ?
C15 C14 H14 119.4 . . ?
C13 C14 H14 119.4 . . ?
C14 C15 C16 120.1(2) . . ?
C14 C15 H15 120.0 . . ?
C16 C15 H15 120.0 . . ?
C15 C16 C11 119.5(2) . . ?
C15 C16 H16 120.3 . . ?
C11 C16 H16 120.3 . . ?
C26 C21 C22 119.94(16) . . ?
C26 C21 C1 126.45(16) . . ?
C22 C21 C1 113.59(15) . . ?
C23 C22 C21 120.45(17) . . ?
C23 C22 C8 126.73(16) . . ?
C21 C22 C8 112.81(15) . . ?
C22 C23 C24 118.88(18) . . ?
C22 C23 H23 120.6 . . ?
C24 C23 H23 120.6 . . ?
C25 C24 C23 120.95(19) . . ?
C25 C24 H24 119.5 . . ?
C23 C24 H24 119.5 . . ?
C24 C25 C26 120.25(19) . . ?
C24 C25 H25 119.9 . . ?
C26 C25 H25 119.9 . . ?
C21 C26 C25 119.50(19) . . ?
C21 C26 H26 120.2 . . ?
C25 C26 H26 120.2 . . ?
C31 N3 C35 120.0 . . ?
N3 C31 C32 120.0 . . ?
N3 C31 H31 120.0 . . ?
C32 C31 H31 120.0 . . ?
C33 C32 C31 120.0 . . ?
C33 C32 H32 120.0 . . ?
C31 C32 H32 120.0 . . ?
C32 C33 C34 120.0 . . ?
C32 C33 C36 121.2(7) . . ?
C34 C33 C36 118.7(7) . . ?
C33 C34 C35 120.0 . . ?
C33 C34 H34 120.0 . . ?
C35 C34 H34 120.0 . . ?
C34 C35 N3 120.0 . . ?
C34 C35 H35 120.0 . . ?
N3 C35 H35 120.0 . . ?
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 . . ?

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 C3 -62.09(18) . . . . ?
C21 C1 C2 C3 -175.89(14) . . . . ?
C11 C1 C2 C5 61.05(17) . . . . ?
C21 C1 C2 C5 -52.76(18) . . . . ?
C4 O1 C3 O2 -2.6(3) . . . . ?
C4 O1 C3 C2 179.08(16) . . . . ?
C5 C2 C3 O2 9.9(3) . . . . ?
C1 C2 C3 O2 132.4(2) . . . . ?
C5 C2 C3 O1 -171.81(15) . . . . ?
C1 C2 C3 O1 -49.32(19) . . . . ?
C3 C2 C5 C6 -117.90(16) . . . . ?
C1 C2 C5 C6 118.99(16) . . . . ?
C3 C2 C5 C8 117.61(15) . . . . ?
C1 C2 C5 C8 -5.50(18) . . . . ?
C7 O3 C6 O4 2.6(3) . . . . ?
C7 O3 C6 C5 -175.95(19) . . . . ?
C2 C5 C6 O4 10.8(3) . . . . ?
C8 C5 C6 O4 133.9(2) . . . . ?
C2 C5 C6 O3 -170.69(15) . . . . ?
C8 C5 C6 O3 -47.6(2) . . . . ?
C6 C5 C8 C22 -63.21(17) . . . . ?
C2 C5 C8 C22 61.35(17) . . . . ?
C6 C5 C8 C12 -177.33(14) . . . . ?
C2 C5 C8 C12 -52.77(17) . . . . ?
C21 C1 C11 C16 -123.96(19) . . . . ?
C2 C1 C11 C16 121.78(19) . . . . ?
C21 C1 C11 C12 55.43(19) . . . . ?
C2 C1 C11 C12 -58.83(18) . . . . ?
C16 C11 C12 C13 -0.3(3) . . . . ?
C1 C11 C12 C13 -179.70(16) . . . . ?
C16 C11 C12 C8 177.86(16) . . . . ?
C1 C11 C12 C8 -1.6(2) . . . . ?
C22 C8 C12 C13 124.27(19) . . . . ?
C5 C8 C12 C13 -122.60(19) . . . . ?
C22 C8 C12 C11 -53.71(18) . . . . ?
C5 C8 C12 C11 59.42(18) . . . . ?
C11 C12 C13 C14 1.1(3) . . . . ?
C8 C12 C13 C14 -176.73(18) . . . . ?
C12 C13 C14 C15 -1.0(3) . . . . ?
C13 C14 C15 C16 -0.1(4) . . . . ?
C14 C15 C16 C11 1.0(3) . . . . ?
C12 C11 C16 C15 -0.8(3) . . . . ?
C1 C11 C16 C15 178.56(19) . . . . ?
C11 C1 C21 C26 123.8(2) . . . . ?
C2 C1 C21 C26 -123.1(2) . . . . ?
C11 C1 C21 C22 -54.35(19) . . . . ?
C2 C1 C21 C22 58.77(19) . . . . ?
C26 C21 C22 C23 1.4(3) . . . . ?
C1 C21 C22 C23 179.65(16) . . . . ?
C26 C21 C22 C8 -179.07(17) . . . . ?
C1 C21 C22 C8 -0.8(2) . . . . ?
C12 C8 C22 C23 -125.78(18) . . . . ?
C5 C8 C22 C23 119.83(19) . . . . ?
C12 C8 C22 C21 54.67(18) . . . . ?
C5 C8 C22 C21 -59.72(18) . . . . ?
C21 C22 C23 C24 -1.7(3) . . . . ?
C8 C22 C23 C24 178.75(18) . . . . ?
C22 C23 C24 C25 0.8(3) . . . . ?
C23 C24 C25 C26 0.5(4) . . . . ?
C22 C21 C26 C25 0.0(3) . . . . ?
C1 C21 C26 C25 -178.1(2) . . . . ?
C24 C25 C26 C21 -0.9(4) . . . . ?
C35 N3 C31 C32 0.0 . . . . ?
N3 C31 C32 C33 0.0 . . . . ?
C31 C32 C33 C34 0.0 . . . . ?
C31 C32 C33 C36 176.0(13) . . . . ?
C32 C33 C34 C35 0.0 . . . . ?
C36 C33 C34 C35 -176.1(12) . . . . ?
C33 C34 C35 N3 0.0 . . . . ?
C31 N3 C35 C34 0.0 . . . . ?

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
C2 H2 O4 0.98 2.32 2.822(3) 111 . yes
C5 H5 O2 0.98 2.28 2.802(2) 113 . yes

_refine_diff_density_max         0.258
_refine_diff_density_min         -0.226
_refine_diff_density_rms         0.050


_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_ja244
_database_code_depnum_ccdc_archive 'CCDC 2236049'
loop_
_audit_author_name
_audit_author_address
'Eric Hosten'
;Nelson Mandela University
South Africa
;
_audit_update_record             
;
2023-01-13 deposited with the CCDC.	2023-02-28 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        
trans-α,α,α',α'-tetraphenyl-9,10-dihydro-9,10-ethanoanthracene-11,12-dimethanol
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         '2(C42 H34 O2), 3(C6 H7 N)'
_chemical_formula_sum            'C102 H89 N3 O4'
_chemical_formula_weight         1420.76

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           15
_space_group_name_H-M_alt        'I 2/a'
_space_group_name_Hall           '-I 2ya'

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

_cell_length_a                   22.263(2)
_cell_length_b                   9.8738(9)
_cell_length_c                   35.777(4)
_cell_angle_alpha                90
_cell_angle_beta                 93.222(6)
_cell_angle_gamma                90
_cell_volume                     7852.1(13)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    9820
_cell_measurement_theta_min      2.21
_cell_measurement_theta_max      28.02

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.202
_exptl_crystal_F_000             3016
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.578
_exptl_crystal_size_mid          0.468
_exptl_crystal_size_min          0.163
_exptl_absorpt_coefficient_mu    0.072
_shelx_estimated_absorpt_T_min   0.959
_shelx_estimated_absorpt_T_max   0.988
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_correction_T_min  0.8501
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_process_details   'SADABS-2008/1 (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            57805
_diffrn_reflns_av_unetI/netI     0.0426
_diffrn_reflns_av_R_equivalents  0.0587
_diffrn_reflns_limit_h_min       -29
_diffrn_reflns_limit_h_max       29
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -47
_diffrn_reflns_limit_l_max       47
_diffrn_reflns_theta_min         1.832
_diffrn_reflns_theta_max         28.484
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             9795
_reflns_number_gt                6486
_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).

One of the 3-methylpyridine solvent/guest molecules is disordered around a 2-
fold rotational axis which necessitated the use of the constraints and
restraints: RIGU and SAME.

A reflection with large difference between its observed and calculated
intensities was omitted. This is due to obstruction by the beam stop.,Solvent disorder
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0658P)²+3.4566P] 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       0.00071(13)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         9795
_refine_ls_number_parameters     528
_refine_ls_number_restraints     60
_refine_ls_R_factor_all          0.0839
_refine_ls_R_factor_gt           0.0507
_refine_ls_wR_factor_ref         0.1514
_refine_ls_wR_factor_gt          0.1291
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_restrained_S_all      1.045
_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 0.52900(5) 0.58548(11) 0.34681(3) 0.0393(2) Uani 1 1 d . . . . .
H1A H 0.556923 0.638510 0.350976 0.059 Uiso 1 1 calc R U . . .
O2 O 0.43250(5) 0.53639(11) 0.30515(3) 0.0430(3) Uani 1 1 d . . . . .
H2A H 0.468014 0.544297 0.312194 0.065 Uiso 1 1 calc R U . . .
C1 C 0.42076(6) 0.52978(15) 0.42406(4) 0.0349(3) Uani 1 1 d . . . . .
H1 H 0.442589 0.461310 0.439295 0.042 Uiso 1 1 calc R U . . .
C2 C 0.44321(6) 0.53575(13) 0.38326(3) 0.0301(3) Uani 1 1 d . . . . .
H2 H 0.425945 0.456605 0.370080 0.036 Uiso 1 1 calc R U . . .
C3 C 0.41465(6) 0.66181(13) 0.36345(3) 0.0315(3) Uani 1 1 d . . . . .
H3 H 0.445165 0.733320 0.365720 0.038 Uiso 1 1 calc R U . . .
C4 C 0.36102(7) 0.71146(15) 0.38656(4) 0.0387(3) Uani 1 1 d . . . . .
H4 H 0.337134 0.781141 0.373068 0.046 Uiso 1 1 calc R U . . .
C5 C 0.51343(6) 0.52354(13) 0.38122(4) 0.0312(3) Uani 1 1 d . . . . .
C6 C 0.39875(6) 0.64427(14) 0.32008(4) 0.0342(3) Uani 1 1 d . . . . .
C11 C 0.42372(7) 0.66760(16) 0.44257(4) 0.0385(3) Uani 1 1 d . . . . .
C12 C 0.39085(7) 0.76625(16) 0.42260(4) 0.0421(3) Uani 1 1 d . . . . .
C13 C 0.38800(9) 0.89713(19) 0.43608(5) 0.0586(5) Uani 1 1 d . . . . .
H13 H 0.366539 0.963233 0.422484 0.070 Uiso 1 1 calc R U . . .
C14 C 0.41753(10) 0.9287(2) 0.47014(6) 0.0715(6) Uani 1 1 d . . . . .
H14 H 0.416138 1.016684 0.479340 0.086 Uiso 1 1 calc R U . . .
C15 C 0.44897(9) 0.8303(2) 0.49046(5) 0.0650(5) Uani 1 1 d . . . . .
H15 H 0.467863 0.852009 0.513523 0.078 Uiso 1 1 calc R U . . .
C16 C 0.45260(8) 0.69964(19) 0.47678(4) 0.0491(4) Uani 1 1 d . . . . .
H16 H 0.474218 0.633879 0.490418 0.059 Uiso 1 1 calc R U . . .
C21 C 0.35455(7) 0.49579(16) 0.41849(4) 0.0392(3) Uani 1 1 d . . . . .
C22 C 0.32240(7) 0.59416(16) 0.39777(4) 0.0401(3) Uani 1 1 d . . . . .
C23 C 0.26083(7) 0.5806(2) 0.39154(5) 0.0529(4) Uani 1 1 d . . . . .
H23 H 0.238872 0.646284 0.378089 0.063 Uiso 1 1 calc R U . . .
C24 C 0.23205(8) 0.4683(2) 0.40548(5) 0.0639(5) Uani 1 1 d . . . . .
H24 H 0.190593 0.459477 0.401509 0.077 Uiso 1 1 calc R U . . .
C25 C 0.26403(9) 0.3703(2) 0.42505(5) 0.0627(5) Uani 1 1 d . . . . .
H25 H 0.244205 0.295083 0.434008 0.075 Uiso 1 1 calc R U . . .
C26 C 0.32582(8) 0.38254(18) 0.43157(4) 0.0491(4) Uani 1 1 d . . . . .
H26 H 0.347625 0.315474 0.444562 0.059 Uiso 1 1 calc R U . . .
C31 C 0.54880(6) 0.59399(14) 0.41367(4) 0.0331(3) Uani 1 1 d . . . . .
C32 C 0.57605(7) 0.52150(16) 0.44330(4) 0.0398(3) Uani 1 1 d . . . . .
H32 H 0.572050 0.427784 0.443974 0.048 Uiso 1 1 calc R U . . .
C33 C 0.60910(8) 0.58715(19) 0.47188(4) 0.0505(4) Uani 1 1 d . . . . .
H33 H 0.626832 0.537355 0.491619 0.061 Uiso 1 1 calc R U . . .
C34 C 0.61579(8) 0.72541(19) 0.47117(5) 0.0555(5) Uani 1 1 d . . . . .
H34 H 0.638639 0.769013 0.490114 0.067 Uiso 1 1 calc R U . . .
C35 C 0.58860(8) 0.79899(18) 0.44237(5) 0.0523(4) Uani 1 1 d . . . . .
H35 H 0.592593 0.892735 0.442037 0.063 Uiso 1 1 calc R U . . .
C36 C 0.55530(7) 0.73431(15) 0.41388(4) 0.0416(3) Uani 1 1 d . . . . .
H36 H 0.536978 0.785237 0.394569 0.050 Uiso 1 1 calc R U . . .
C41 C 0.53228(6) 0.37378(14) 0.37873(4) 0.0352(3) Uani 1 1 d . . . . .
C42 C 0.49896(8) 0.26764(16) 0.39207(5) 0.0491(4) Uani 1 1 d . . . . .
H42 H 0.462823 0.285629 0.402923 0.059 Uiso 1 1 calc R U . . .
C43 C 0.51872(10) 0.13438(18) 0.38947(6) 0.0641(5) Uani 1 1 d . . . . .
H43 H 0.496034 0.064396 0.398874 0.077 Uiso 1 1 calc R U . . .
C44 C 0.57127(11) 0.1060(2) 0.37318(6) 0.0714(6) Uani 1 1 d . . . . .
H44 H 0.584098 0.016851 0.371025 0.086 Uiso 1 1 calc R U . . .
C45 C 0.60500(10) 0.2100(2) 0.36001(6) 0.0664(5) Uani 1 1 d . . . . .
H45 H 0.641034 0.191367 0.349109 0.080 Uiso 1 1 calc R U . . .
C46 C 0.58573(8) 0.34232(17) 0.36284(5) 0.0487(4) Uani 1 1 d . . . . .
H46 H 0.609202 0.411761 0.353872 0.058 Uiso 1 1 calc R U . . .
C51 C 0.41420(6) 0.77566(16) 0.29939(4) 0.0401(3) Uani 1 1 d . . . . .
C52 C 0.42712(8) 0.7665(2) 0.26182(5) 0.0541(4) Uani 1 1 d . . . . .
H52 H 0.424698 0.682932 0.249836 0.065 Uiso 1 1 calc R U . . .
C53 C 0.44346(9) 0.8797(3) 0.24210(6) 0.0711(6) Uani 1 1 d . . . . .
H53 H 0.452381 0.871466 0.217117 0.085 Uiso 1 1 calc R U . . .
C54 C 0.44661(10) 1.0033(3) 0.25898(7) 0.0786(7) Uani 1 1 d . . . . .
H54 H 0.458061 1.078967 0.245628 0.094 Uiso 1 1 calc R U . . .
C55 C 0.43283(10) 1.0162(2) 0.29586(7) 0.0728(6) Uani 1 1 d . . . . .
H55 H 0.434213 1.100666 0.307358 0.087 Uiso 1 1 calc R U . . .
C56 C 0.41681(8) 0.90199(17) 0.31585(5) 0.0543(4) Uani 1 1 d . . . . .
H56 H 0.407700 0.911079 0.340777 0.065 Uiso 1 1 calc R U . . .
C61 C 0.33321(7) 0.60342(15) 0.31088(4) 0.0371(3) Uani 1 1 d . . . . .
C62 C 0.31723(8) 0.46761(17) 0.31097(5) 0.0503(4) Uani 1 1 d . . . . .
H62 H 0.346143 0.402368 0.317360 0.060 Uiso 1 1 calc R U . . .
C63 C 0.25853(10) 0.4284(2) 0.30160(6) 0.0680(6) Uani 1 1 d . . . . .
H63 H 0.248463 0.337009 0.301856 0.082 Uiso 1 1 calc R U . . .
C64 C 0.21526(9) 0.5221(3) 0.29201(6) 0.0702(6) Uani 1 1 d . . . . .
H64 H 0.176009 0.494785 0.285735 0.084 Uiso 1 1 calc R U . . .
C65 C 0.23010(8) 0.6564(2) 0.29171(5) 0.0625(5) Uani 1 1 d . . . . .
H65 H 0.200772 0.720759 0.285329 0.075 Uiso 1 1 calc R U . . .
C66 C 0.28862(7) 0.69717(18) 0.30088(4) 0.0477(4) Uani 1 1 d . . . . .
H66 H 0.298230 0.788787 0.300327 0.057 Uiso 1 1 calc R U . . .
N7 N 0.61321(7) 0.77387(14) 0.33289(4) 0.0510(3) Uani 1 1 d D . . . .
C71 C 0.70357(9) 0.90267(19) 0.32958(6) 0.0621(5) Uani 1 1 d D . . . .
C72 C 0.66645(8) 0.81443(18) 0.34716(5) 0.0548(4) Uani 1 1 d D . . . .
H72 H 0.679565 0.781148 0.370531 0.066 Uiso 1 1 calc R U . . .
C73 C 0.59449(9) 0.82405(19) 0.29992(5) 0.0576(5) Uani 1 1 d D . . . .
H73 H 0.556610 0.799251 0.289926 0.069 Uiso 1 1 calc R U . . .
C74 C 0.62822(11) 0.9104(2) 0.27994(6) 0.0707(6) Uani 1 1 d D . . . .
H74 H 0.613985 0.942359 0.256640 0.085 Uiso 1 1 calc R U . . .
C75 C 0.68325(11) 0.9489(2) 0.29492(6) 0.0729(6) Uani 1 1 d D . . . .
H75 H 0.707165 1.006653 0.281601 0.087 Uiso 1 1 calc R U . . .
C76 C 0.76352(13) 0.9401(3) 0.34820(11) 0.1218(11) Uani 1 1 d D . . . .
H76A H 0.776858 0.869021 0.364995 0.183 Uiso 1 1 calc R U . . .
H76B H 0.759641 1.022741 0.361990 0.183 Uiso 1 1 calc R U . . .
H76C H 0.792319 0.952396 0.329504 0.183 Uiso 1 1 calc R U . . .
N8 N 0.2719(3) 1.0122(7) 0.5331(2) 0.133(2) Uani 0.5 1 d D . P A -1
C81 C 0.2343(5) 0.8763(13) 0.4811(3) 0.154(4) Uani 0.5 1 d D . P A -1
C82 C 0.2436(11) 1.0085(12) 0.4978(5) 0.182(5) Uani 0.5 1 d D . P A -1
H82 H 0.231142 1.087112 0.485288 0.218 Uiso 0.5 1 calc R U P A -1
C83 C 0.2858(10) 0.8880(16) 0.5437(5) 0.195(6) Uani 0.5 1 d D . P A -1
H83 H 0.297092 0.889189 0.569082 0.234 Uiso 0.5 1 calc R U P A -1
C84 C 0.2898(6) 0.7617(13) 0.5314(3) 0.199(5) Uani 0.5 1 d D . P A -1
H84 H 0.307824 0.686683 0.543101 0.239 Uiso 0.5 1 calc R U P A -1
C85 C 0.2605(5) 0.7717(11) 0.4974(4) 0.150(4) Uani 0.5 1 d D . P A -1
H85 H 0.258749 0.692117 0.483487 0.180 Uiso 0.5 1 calc R U P A -1
C86 C 0.1990(13) 0.875(3) 0.4468(5) 0.283(12) Uani 0.5 1 d D . P A -1
H86A H 0.196660 0.965456 0.436757 0.424 Uiso 0.5 1 calc R U P A -1
H86B H 0.159306 0.843274 0.451083 0.424 Uiso 0.5 1 calc R U P A -1
H86C H 0.217317 0.816565 0.429307 0.424 Uiso 0.5 1 calc R U P A -1


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C5 1.4348(16) . ?
O1 H1A 0.8200 . ?
O2 C6 1.4247(17) . ?
O2 H2A 0.8200 . ?
C1 C11 1.513(2) . ?
C1 C21 1.514(2) . ?
C1 C2 1.5705(19) . ?
C1 H1 0.9800 . ?
C2 C3 1.5508(18) . ?
C2 C5 1.5736(19) . ?
C2 H2 0.9800 . ?
C3 C4 1.568(2) . ?
C3 C6 1.5817(18) . ?
C3 H3 0.9800 . ?
C4 C22 1.510(2) . ?
C4 C12 1.516(2) . ?
C4 H4 0.9800 . ?
C5 C31 1.5326(18) . ?
C5 C41 1.5411(19) . ?
C6 C61 1.532(2) . ?
C6 C51 1.542(2) . ?
C11 C16 1.387(2) . ?
C11 C12 1.391(2) . ?
C12 C13 1.382(2) . ?
C13 C14 1.387(3) . ?
C13 H13 0.9300 . ?
C14 C15 1.380(3) . ?
C14 H14 0.9300 . ?
C15 C16 1.384(3) . ?
C15 H15 0.9300 . ?
C16 H16 0.9300 . ?
C21 C26 1.383(2) . ?
C21 C22 1.395(2) . ?
C22 C23 1.383(2) . ?
C23 C24 1.387(3) . ?
C23 H23 0.9300 . ?
C24 C25 1.370(3) . ?
C24 H24 0.9300 . ?
C25 C26 1.388(2) . ?
C25 H25 0.9300 . ?
C26 H26 0.9300 . ?
C31 C32 1.3899(19) . ?
C31 C36 1.393(2) . ?
C32 C33 1.387(2) . ?
C32 H32 0.9300 . ?
C33 C34 1.374(2) . ?
C33 H33 0.9300 . ?
C34 C35 1.373(3) . ?
C34 H34 0.9300 . ?
C35 C36 1.383(2) . ?
C35 H35 0.9300 . ?
C36 H36 0.9300 . ?
C41 C46 1.383(2) . ?
C41 C42 1.384(2) . ?
C42 C43 1.392(2) . ?
C42 H42 0.9300 . ?
C43 C44 1.365(3) . ?
C43 H43 0.9300 . ?
C44 C45 1.371(3) . ?
C44 H44 0.9300 . ?
C45 C46 1.380(2) . ?
C45 H45 0.9300 . ?
C46 H46 0.9300 . ?
C51 C56 1.379(2) . ?
C51 C52 1.393(2) . ?
C52 C53 1.382(3) . ?
C52 H52 0.9300 . ?
C53 C54 1.362(3) . ?
C53 H53 0.9300 . ?
C54 C55 1.377(3) . ?
C54 H54 0.9300 . ?
C55 C56 1.392(3) . ?
C55 H55 0.9300 . ?
C56 H56 0.9300 . ?
C61 C62 1.387(2) . ?
C61 C66 1.389(2) . ?
C62 C63 1.386(3) . ?
C62 H62 0.9300 . ?
C63 C64 1.366(3) . ?
C63 H63 0.9300 . ?
C64 C65 1.367(3) . ?
C64 H64 0.9300 . ?
C65 C66 1.385(2) . ?
C65 H65 0.9300 . ?
C66 H66 0.9300 . ?
N7 C73 1.325(2) . ?
N7 C72 1.326(2) . ?
C71 C75 1.374(3) . ?
C71 C72 1.377(3) . ?
C71 C76 1.504(3) . ?
C72 H72 0.9300 . ?
C73 C74 1.365(3) . ?
C73 H73 0.9300 . ?
C74 C75 1.363(3) . ?
C74 H74 0.9300 . ?
C75 H75 0.9300 . ?
C76 H76A 0.9600 . ?
C76 H76B 0.9600 . ?
C76 H76C 0.9600 . ?
N8 C83 1.315(14) . ?
N8 C82 1.382(16) . ?
C81 C85 1.306(12) . ?
C81 C86 1.421(14) . ?
C81 C82 1.444(12) . ?
C82 H82 0.9300 . ?
C83 C84 1.326(15) . ?
C83 H83 0.9300 . ?
C84 C85 1.352(16) . ?
C84 H84 0.9300 . ?
C85 H85 0.9300 . ?
C86 H86A 0.9600 . ?
C86 H86B 0.9600 . ?
C86 H86C 0.9600 . ?

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 O2 H2A 109.5 . . ?
C11 C1 C21 105.97(12) . . ?
C11 C1 C2 111.39(11) . . ?
C21 C1 C2 104.14(10) . . ?
C11 C1 H1 111.7 . . ?
C21 C1 H1 111.7 . . ?
C2 C1 H1 111.7 . . ?
C3 C2 C1 108.12(11) . . ?
C3 C2 C5 115.04(11) . . ?
C1 C2 C5 114.14(10) . . ?
C3 C2 H2 106.3 . . ?
C1 C2 H2 106.3 . . ?
C5 C2 H2 106.3 . . ?
C2 C3 C4 108.35(11) . . ?
C2 C3 C6 115.07(11) . . ?
C4 C3 C6 114.60(11) . . ?
C2 C3 H3 106.0 . . ?
C4 C3 H3 106.0 . . ?
C6 C3 H3 106.0 . . ?
C22 C4 C12 106.06(12) . . ?
C22 C4 C3 111.22(12) . . ?
C12 C4 C3 104.46(12) . . ?
C22 C4 H4 111.6 . . ?
C12 C4 H4 111.6 . . ?
C3 C4 H4 111.6 . . ?
O1 C5 C31 108.53(11) . . ?
O1 C5 C41 106.24(11) . . ?
C31 C5 C41 110.44(11) . . ?
O1 C5 C2 107.20(10) . . ?
C31 C5 C2 113.56(11) . . ?
C41 C5 C2 110.53(11) . . ?
O2 C6 C61 103.81(11) . . ?
O2 C6 C51 108.21(12) . . ?
C61 C6 C51 110.74(11) . . ?
O2 C6 C3 110.85(10) . . ?
C61 C6 C3 113.43(11) . . ?
C51 C6 C3 109.58(11) . . ?
C16 C11 C12 119.86(15) . . ?
C16 C11 C1 126.73(15) . . ?
C12 C11 C1 113.34(12) . . ?
C13 C12 C11 120.56(15) . . ?
C13 C12 C4 127.15(15) . . ?
C11 C12 C4 112.30(13) . . ?
C12 C13 C14 119.21(19) . . ?
C12 C13 H13 120.4 . . ?
C14 C13 H13 120.4 . . ?
C15 C14 C13 120.37(18) . . ?
C15 C14 H14 119.8 . . ?
C13 C14 H14 119.8 . . ?
C14 C15 C16 120.54(17) . . ?
C14 C15 H15 119.7 . . ?
C16 C15 H15 119.7 . . ?
C15 C16 C11 119.43(18) . . ?
C15 C16 H16 120.3 . . ?
C11 C16 H16 120.3 . . ?
C26 C21 C22 120.64(14) . . ?
C26 C21 C1 126.88(14) . . ?
C22 C21 C1 112.48(13) . . ?
C23 C22 C21 119.52(15) . . ?
C23 C22 C4 127.27(15) . . ?
C21 C22 C4 113.10(13) . . ?
C22 C23 C24 119.55(17) . . ?
C22 C23 H23 120.2 . . ?
C24 C23 H23 120.2 . . ?
C25 C24 C23 120.72(17) . . ?
C25 C24 H24 119.6 . . ?
C23 C24 H24 119.6 . . ?
C24 C25 C26 120.40(18) . . ?
C24 C25 H25 119.8 . . ?
C26 C25 H25 119.8 . . ?
C21 C26 C25 119.12(17) . . ?
C21 C26 H26 120.4 . . ?
C25 C26 H26 120.4 . . ?
C32 C31 C36 117.86(13) . . ?
C32 C31 C5 121.85(12) . . ?
C36 C31 C5 120.28(12) . . ?
C33 C32 C31 120.83(15) . . ?
C33 C32 H32 119.6 . . ?
C31 C32 H32 119.6 . . ?
C34 C33 C32 120.30(15) . . ?
C34 C33 H33 119.9 . . ?
C32 C33 H33 119.9 . . ?
C35 C34 C33 119.75(15) . . ?
C35 C34 H34 120.1 . . ?
C33 C34 H34 120.1 . . ?
C34 C35 C36 120.28(16) . . ?
C34 C35 H35 119.9 . . ?
C36 C35 H35 119.9 . . ?
C35 C36 C31 120.97(15) . . ?
C35 C36 H36 119.5 . . ?
C31 C36 H36 119.5 . . ?
C46 C41 C42 117.51(14) . . ?
C46 C41 C5 118.87(13) . . ?
C42 C41 C5 123.61(13) . . ?
C41 C42 C43 121.01(17) . . ?
C41 C42 H42 119.5 . . ?
C43 C42 H42 119.5 . . ?
C44 C43 C42 120.27(18) . . ?
C44 C43 H43 119.9 . . ?
C42 C43 H43 119.9 . . ?
C43 C44 C45 119.47(17) . . ?
C43 C44 H44 120.3 . . ?
C45 C44 H44 120.3 . . ?
C44 C45 C46 120.35(19) . . ?
C44 C45 H45 119.8 . . ?
C46 C45 H45 119.8 . . ?
C45 C46 C41 121.39(17) . . ?
C45 C46 H46 119.3 . . ?
C41 C46 H46 119.3 . . ?
C56 C51 C52 117.68(15) . . ?
C56 C51 C6 124.14(14) . . ?
C52 C51 C6 118.17(15) . . ?
C53 C52 C51 120.97(19) . . ?
C53 C52 H52 119.5 . . ?
C51 C52 H52 119.5 . . ?
C54 C53 C52 120.5(2) . . ?
C54 C53 H53 119.8 . . ?
C52 C53 H53 119.8 . . ?
C53 C54 C55 119.92(18) . . ?
C53 C54 H54 120.0 . . ?
C55 C54 H54 120.0 . . ?
C54 C55 C56 119.7(2) . . ?
C54 C55 H55 120.2 . . ?
C56 C55 H55 120.2 . . ?
C51 C56 C55 121.26(19) . . ?
C51 C56 H56 119.4 . . ?
C55 C56 H56 119.4 . . ?
C62 C61 C66 117.72(15) . . ?
C62 C61 C6 119.69(13) . . ?
C66 C61 C6 122.55(14) . . ?
C63 C62 C61 120.51(17) . . ?
C63 C62 H62 119.7 . . ?
C61 C62 H62 119.7 . . ?
C64 C63 C62 120.91(19) . . ?
C64 C63 H63 119.5 . . ?
C62 C63 H63 119.5 . . ?
C63 C64 C65 119.48(18) . . ?
C63 C64 H64 120.3 . . ?
C65 C64 H64 120.3 . . ?
C64 C65 C66 120.28(19) . . ?
C64 C65 H65 119.9 . . ?
C66 C65 H65 119.9 . . ?
C65 C66 C61 121.09(17) . . ?
C65 C66 H66 119.5 . . ?
C61 C66 H66 119.5 . . ?
C73 N7 C72 117.36(15) . . ?
C75 C71 C72 116.52(19) . . ?
C75 C71 C76 123.9(2) . . ?
C72 C71 C76 119.6(2) . . ?
N7 C72 C71 124.18(18) . . ?
N7 C72 H72 117.9 . . ?
C71 C72 H72 117.9 . . ?
N7 C73 C74 123.04(19) . . ?
N7 C73 H73 118.5 . . ?
C74 C73 H73 118.5 . . ?
C75 C74 C73 118.47(19) . . ?
C75 C74 H74 120.8 . . ?
C73 C74 H74 120.8 . . ?
C74 C75 C71 120.38(18) . . ?
C74 C75 H75 119.8 . . ?
C71 C75 H75 119.8 . . ?
C71 C76 H76A 109.5 . . ?
C71 C76 H76B 109.5 . . ?
H76A C76 H76B 109.5 . . ?
C71 C76 H76C 109.5 . . ?
H76A C76 H76C 109.5 . . ?
H76B C76 H76C 109.5 . . ?
C83 N8 C82 109.0(10) . . ?
C85 C81 C86 126.3(15) . . ?
C85 C81 C82 118.8(12) . . ?
C86 C81 C82 114.9(15) . . ?
N8 C82 C81 116.6(11) . . ?
N8 C82 H82 121.7 . . ?
C81 C82 H82 121.7 . . ?
N8 C83 C84 143.3(16) . . ?
N8 C83 H83 108.3 . . ?
C84 C83 H83 108.3 . . ?
C83 C84 C85 101.0(11) . . ?
C83 C84 H84 129.5 . . ?
C85 C84 H84 129.5 . . ?
C81 C85 C84 129.8(13) . . ?
C81 C85 H85 115.1 . . ?
C84 C85 H85 115.1 . . ?
C81 C86 H86A 109.5 . . ?
C81 C86 H86B 109.5 . . ?
H86A C86 H86B 109.5 . . ?
C81 C86 H86C 109.5 . . ?
H86A C86 H86C 109.5 . . ?
H86B C86 H86C 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 C3 -44.73(15) . . . . ?
C21 C1 C2 C3 69.06(13) . . . . ?
C11 C1 C2 C5 84.67(14) . . . . ?
C21 C1 C2 C5 -161.54(11) . . . . ?
C1 C2 C3 C4 -15.90(14) . . . . ?
C5 C2 C3 C4 -144.80(11) . . . . ?
C1 C2 C3 C6 -145.65(11) . . . . ?
C5 C2 C3 C6 85.46(14) . . . . ?
C2 C3 C4 C22 -44.98(15) . . . . ?
C6 C3 C4 C22 85.02(14) . . . . ?
C2 C3 C4 C12 69.00(14) . . . . ?
C6 C3 C4 C12 -160.99(12) . . . . ?
C3 C2 C5 O1 -30.37(14) . . . . ?
C1 C2 C5 O1 -156.22(11) . . . . ?
C3 C2 C5 C31 89.49(13) . . . . ?
C1 C2 C5 C31 -36.36(15) . . . . ?
C3 C2 C5 C41 -145.75(11) . . . . ?
C1 C2 C5 C41 88.41(13) . . . . ?
C2 C3 C6 O2 -20.84(16) . . . . ?
C4 C3 C6 O2 -147.45(12) . . . . ?
C2 C3 C6 C61 95.49(14) . . . . ?
C4 C3 C6 C61 -31.13(16) . . . . ?
C2 C3 C6 C51 -140.20(12) . . . . ?
C4 C3 C6 C51 93.18(14) . . . . ?
C21 C1 C11 C16 121.44(16) . . . . ?
C2 C1 C11 C16 -125.92(15) . . . . ?
C21 C1 C11 C12 -55.39(15) . . . . ?
C2 C1 C11 C12 57.26(16) . . . . ?
C16 C11 C12 C13 1.7(2) . . . . ?
C1 C11 C12 C13 178.78(15) . . . . ?
C16 C11 C12 C4 -178.24(14) . . . . ?
C1 C11 C12 C4 -1.18(18) . . . . ?
C22 C4 C12 C13 -123.19(18) . . . . ?
C3 C4 C12 C13 119.22(17) . . . . ?
C22 C4 C12 C11 56.76(16) . . . . ?
C3 C4 C12 C11 -60.83(16) . . . . ?
C11 C12 C13 C14 -1.0(3) . . . . ?
C4 C12 C13 C14 178.91(17) . . . . ?
C12 C13 C14 C15 -0.5(3) . . . . ?
C13 C14 C15 C16 1.4(3) . . . . ?
C14 C15 C16 C11 -0.8(3) . . . . ?
C12 C11 C16 C15 -0.8(2) . . . . ?
C1 C11 C16 C15 -177.45(15) . . . . ?
C11 C1 C21 C26 -123.43(16) . . . . ?
C2 C1 C21 C26 118.97(16) . . . . ?
C11 C1 C21 C22 56.49(15) . . . . ?
C2 C1 C21 C22 -61.10(15) . . . . ?
C26 C21 C22 C23 2.5(2) . . . . ?
C1 C21 C22 C23 -177.41(13) . . . . ?
C26 C21 C22 C4 178.89(13) . . . . ?
C1 C21 C22 C4 -1.04(17) . . . . ?
C12 C4 C22 C23 120.39(16) . . . . ?
C3 C4 C22 C23 -126.62(16) . . . . ?
C12 C4 C22 C21 -55.63(16) . . . . ?
C3 C4 C22 C21 57.35(16) . . . . ?
C21 C22 C23 C24 -1.0(2) . . . . ?
C4 C22 C23 C24 -176.79(15) . . . . ?
C22 C23 C24 C25 -0.6(3) . . . . ?
C23 C24 C25 C26 0.7(3) . . . . ?
C22 C21 C26 C25 -2.4(2) . . . . ?
C1 C21 C26 C25 177.48(15) . . . . ?
C24 C25 C26 C21 0.8(3) . . . . ?
O1 C5 C31 C32 -137.13(13) . . . . ?
C41 C5 C31 C32 -21.05(18) . . . . ?
C2 C5 C31 C32 103.76(15) . . . . ?
O1 C5 C31 C36 41.87(17) . . . . ?
C41 C5 C31 C36 157.95(13) . . . . ?
C2 C5 C31 C36 -77.23(16) . . . . ?
C36 C31 C32 C33 -0.7(2) . . . . ?
C5 C31 C32 C33 178.36(14) . . . . ?
C31 C32 C33 C34 -0.5(3) . . . . ?
C32 C33 C34 C35 1.3(3) . . . . ?
C33 C34 C35 C36 -0.9(3) . . . . ?
C34 C35 C36 C31 -0.2(3) . . . . ?
C32 C31 C36 C35 1.0(2) . . . . ?
C5 C31 C36 C35 -178.04(14) . . . . ?
O1 C5 C41 C46 39.66(16) . . . . ?
C31 C5 C41 C46 -77.85(16) . . . . ?
C2 C5 C41 C46 155.63(12) . . . . ?
O1 C5 C41 C42 -141.27(14) . . . . ?
C31 C5 C41 C42 101.22(16) . . . . ?
C2 C5 C41 C42 -25.30(18) . . . . ?
C46 C41 C42 C43 -0.1(2) . . . . ?
C5 C41 C42 C43 -179.13(15) . . . . ?
C41 C42 C43 C44 -0.9(3) . . . . ?
C42 C43 C44 C45 1.2(3) . . . . ?
C43 C44 C45 C46 -0.6(3) . . . . ?
C44 C45 C46 C41 -0.3(3) . . . . ?
C42 C41 C46 C45 0.6(2) . . . . ?
C5 C41 C46 C45 179.73(15) . . . . ?
O2 C6 C51 C56 -145.82(15) . . . . ?
C61 C6 C51 C56 101.02(17) . . . . ?
C3 C6 C51 C56 -24.84(19) . . . . ?
O2 C6 C51 C52 33.34(17) . . . . ?
C61 C6 C51 C52 -79.81(16) . . . . ?
C3 C6 C51 C52 154.32(13) . . . . ?
C56 C51 C52 C53 1.6(2) . . . . ?
C6 C51 C52 C53 -177.59(15) . . . . ?
C51 C52 C53 C54 -0.8(3) . . . . ?
C52 C53 C54 C55 -0.7(3) . . . . ?
C53 C54 C55 C56 1.2(3) . . . . ?
C52 C51 C56 C55 -1.1(3) . . . . ?
C6 C51 C56 C55 178.05(16) . . . . ?
C54 C55 C56 C51 -0.3(3) . . . . ?
O2 C6 C61 C62 34.00(17) . . . . ?
C51 C6 C61 C62 149.92(14) . . . . ?
C3 C6 C61 C62 -86.40(16) . . . . ?
O2 C6 C61 C66 -143.43(14) . . . . ?
C51 C6 C61 C66 -27.51(19) . . . . ?
C3 C6 C61 C66 96.17(16) . . . . ?
C66 C61 C62 C63 -0.5(2) . . . . ?
C6 C61 C62 C63 -178.03(15) . . . . ?
C61 C62 C63 C64 0.2(3) . . . . ?
C62 C63 C64 C65 -0.1(3) . . . . ?
C63 C64 C65 C66 0.3(3) . . . . ?
C64 C65 C66 C61 -0.6(3) . . . . ?
C62 C61 C66 C65 0.7(2) . . . . ?
C6 C61 C66 C65 178.18(15) . . . . ?
C73 N7 C72 C71 -1.3(3) . . . . ?
C75 C71 C72 N7 -0.7(3) . . . . ?
C76 C71 C72 N7 -179.1(2) . . . . ?
C72 N7 C73 C74 2.3(3) . . . . ?
N7 C73 C74 C75 -1.3(3) . . . . ?
C73 C74 C75 C71 -0.9(3) . . . . ?
C72 C71 C75 C74 1.8(3) . . . . ?
C76 C71 C75 C74 -179.9(2) . . . . ?
C83 N8 C82 C81 2(2) . . . . ?
C85 C81 C82 N8 -10(3) . . . . ?
C86 C81 C82 N8 173(2) . . . . ?
C82 N8 C83 C84 12(4) . . . . ?
N8 C83 C84 C85 -12(4) . . . . ?
C86 C81 C85 C84 -173(2) . . . . ?
C82 C81 C85 C84 10(2) . . . . ?
C83 C84 C85 C81 -1.2(19) . . . . ?

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 N7 0.82 1.97 2.7069(17) 150 . yes
O2 H2A O1 0.82 1.83 2.5907(14) 153 . yes
C74 H74 O2 0.93 2.56 3.490(2) 176 4 yes

_refine_diff_density_max         0.533
_refine_diff_density_min         -0.245
_refine_diff_density_rms         0.046


_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_ma075
_database_code_depnum_ccdc_archive 'CCDC 2236045'
loop_
_audit_author_name
_audit_author_address
'Eric Hosten'
;Nelson Mandela University
South Africa
;
_audit_update_record             
;
2023-01-13 deposited with the CCDC.	2023-02-28 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        
'trans-dimethyl 9,10-dihydro-9,10- ethanoanthracene-11,12-dicarboxylate'
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         '2(C20 H18 O4), C6 H7 N'
_chemical_formula_sum            'C46 H43 N O8'
_chemical_formula_weight         737.81

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           60
_space_group_name_H-M_alt        'P b c n'
_space_group_name_Hall           '-P 2n 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+1/2, z+1/2'
'-x, y, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y-1/2, -z-1/2'
'x, -y, z-1/2'
'-x-1/2, y-1/2, z'

_cell_length_a                   21.3960(12)
_cell_length_b                   15.5788(9)
_cell_length_c                   11.3832(6)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3794.3(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    200(2)
_cell_measurement_reflns_used    9812
_cell_measurement_theta_min      2.22
_cell_measurement_theta_max      28.19

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.292
_exptl_crystal_F_000             1560
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.902
_exptl_crystal_size_mid          0.662
_exptl_crystal_size_min          0.570
_exptl_absorpt_coefficient_mu    0.088
_shelx_estimated_absorpt_T_min   0.925
_shelx_estimated_absorpt_T_max   0.952
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_correction_T_min  0.9509
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_process_details   'SADABS-2008/1 (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            51807
_diffrn_reflns_av_unetI/netI     0.0142
_diffrn_reflns_av_R_equivalents  0.0245
_diffrn_reflns_limit_h_min       -27
_diffrn_reflns_limit_h_max       28
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         1.617
_diffrn_reflns_theta_max         28.321
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             4716
_reflns_number_gt                3750
_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 2-methylpyridine solvent/guest molecule is extensively disordered around a
2-fold rotational axis. Residual electron density indicates that the solvent has
additional disorder orientations but attempts to include them were unsuccessful.
The disorder necessitated the use of various restraints and constraints: RIGU,
FLAT and ISOR. The benzene ring was was forced into a regular hexagon with bond
lengths 1.39 Å (AFIX 66 in the SHELXL program (Sheldrick, 2015)).

A number of reflections have higher observed than calculated intensities. This
could be due to small amount of twinning. Twinning routines were unsuccessful.

A number reflections with large differences between their observed and
calculated intensities were omitted. This is due to obstruction by the beam stop
and twinning.,Solvent disorder
;


_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1422P)²+2.0836P] 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     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4716
_refine_ls_number_parameters     271
_refine_ls_number_restraints     91
_refine_ls_R_factor_all          0.0841
_refine_ls_R_factor_gt           0.0695
_refine_ls_wR_factor_ref         0.2290
_refine_ls_wR_factor_gt          0.2090
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_restrained_S_all      1.091
_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
O2 O 0.58658(7) 0.51289(11) 0.28926(14) 0.0500(4) Uani 1 1 d . . . . .
O3 O 0.76175(8) 0.55259(9) 0.54016(12) 0.0407(4) Uani 1 1 d . . . . .
O4 O 0.77280(9) 0.56151(12) 0.34543(14) 0.0587(5) Uani 1 1 d . . . . .
O1 O 0.60966(6) 0.41693(10) 0.14964(12) 0.0393(4) Uani 1 1 d . . . . .
C1 C 0.68764(8) 0.33196(12) 0.31164(15) 0.0304(4) Uani 1 1 d . . . . .
H1 H 0.684710 0.303902 0.232828 0.037 Uiso 1 1 calc R U . . .
C7 C 0.74674(9) 0.53244(12) 0.42986(16) 0.0329(4) Uani 1 1 d . . . . .
C8 C 0.81090(14) 0.61460(18) 0.5553(2) 0.0594(7) Uani 1 1 d . . . . .
H8A H 0.847760 0.596561 0.510608 0.089 Uiso 1 1 calc R U . . .
H8B H 0.821683 0.618790 0.638814 0.089 Uiso 1 1 calc R U . . .
H8C H 0.796729 0.670709 0.526939 0.089 Uiso 1 1 calc R U . . .
C11 C 0.63503(8) 0.30502(12) 0.39232(16) 0.0318(4) Uani 1 1 d . . . . .
C12 C 0.63917(8) 0.34218(11) 0.50432(16) 0.0300(4) Uani 1 1 d . . . . .
C13 C 0.59419(9) 0.32409(13) 0.58873(19) 0.0390(4) Uani 1 1 d . . . . .
H13 H 0.596400 0.349614 0.664406 0.047 Uiso 1 1 calc R U . . .
C14 C 0.54568(10) 0.26781(17) 0.5606(2) 0.0517(6) Uani 1 1 d . . . . .
H14 H 0.514996 0.254586 0.618150 0.062 Uiso 1 1 calc R U . . .
C15 C 0.54156(11) 0.23086(16) 0.4499(2) 0.0512(6) Uani 1 1 d . . . . .
H15 H 0.508393 0.192411 0.432269 0.061 Uiso 1 1 calc R U . . .
C16 C 0.58605(10) 0.25018(13) 0.3647(2) 0.0419(5) Uani 1 1 d . . . . .
H16 H 0.582929 0.226022 0.288332 0.050 Uiso 1 1 calc R U . . .
C21 C 0.74835(8) 0.31037(12) 0.37410(15) 0.0298(4) Uani 1 1 d . . . . .
C22 C 0.75291(8) 0.34630(11) 0.48650(15) 0.0285(4) Uani 1 1 d . . . . .
C23 C 0.80525(9) 0.33161(14) 0.55574(16) 0.0361(4) Uani 1 1 d . . . . .
H23 H 0.808749 0.357031 0.631315 0.043 Uiso 1 1 calc R U . . .
C24 C 0.85260(10) 0.27887(16) 0.51240(19) 0.0454(5) Uani 1 1 d . . . . .
H24 H 0.888535 0.267961 0.559098 0.054 Uiso 1 1 calc R U . . .
C25 C 0.84773(10) 0.24225(16) 0.4019(2) 0.0466(5) Uani 1 1 d . . . . .
H25 H 0.880148 0.206006 0.373789 0.056 Uiso 1 1 calc R U . . .
C26 C 0.79560(10) 0.25816(14) 0.33164(17) 0.0383(4) Uani 1 1 d . . . . .
H26 H 0.792552 0.233465 0.255546 0.046 Uiso 1 1 calc R U . . .
C2 C 0.68299(8) 0.43190(12) 0.30329(15) 0.0287(4) Uani 1 1 d . . . . .
H2 H 0.717537 0.452904 0.251568 0.034 Uiso 1 1 calc R U . . .
C3 C 0.69147(8) 0.47185(11) 0.42604(15) 0.0280(4) Uani 1 1 d . . . . .
H3 H 0.653121 0.506199 0.443673 0.034 Uiso 1 1 calc R U . . .
C4 C 0.69607(8) 0.39923(11) 0.52021(14) 0.0279(4) Uani 1 1 d . . . . .
H4 H 0.699235 0.422594 0.601815 0.033 Uiso 1 1 calc R U . . .
C5 C 0.62104(8) 0.45910(12) 0.24924(16) 0.0310(4) Uani 1 1 d . . . . .
C6 C 0.55111(9) 0.43641(16) 0.0919(2) 0.0436(5) Uani 1 1 d . . . . .
H6A H 0.552668 0.416209 0.010385 0.065 Uiso 1 1 calc R U . . .
H6B H 0.544166 0.498586 0.092843 0.065 Uiso 1 1 calc R U . . .
H6C H 0.516842 0.407629 0.133236 0.065 Uiso 1 1 calc R U . . .
N3 N 0.4764(4) 1.0455(4) 0.2949(8) 0.200(5) Uani 0.5 1 d G U P A -1
C31 C 0.5245(3) 0.9860(5) 0.2862(8) 0.115(3) Uani 0.5 1 d G U P A -1
C32 C 0.5149(4) 0.9092(4) 0.2265(9) 0.156(5) Uani 0.5 1 d G U P A -1
H32 H 0.547833 0.868519 0.220516 0.187 Uiso 0.5 1 calc R U P A -1
C33 C 0.4572(4) 0.8921(5) 0.1755(9) 0.196(6) Uani 0.5 1 d G U P A -1
H33 H 0.450699 0.839665 0.134702 0.235 Uiso 0.5 1 calc R U P A -1
C34 C 0.4091(3) 0.9517(6) 0.1842(8) 0.138(4) Uani 0.5 1 d G U P A -1
H34 H 0.369665 0.939966 0.149371 0.165 Uiso 0.5 1 calc R U P A -1
C35 C 0.4187(3) 1.0284(5) 0.2439(9) 0.131(3) Uani 0.5 1 d G U P A -1
H35 H 0.385765 1.069123 0.249853 0.157 Uiso 0.5 1 calc R U P A -1
C36 C 0.5689(9) 0.9976(13) 0.3639(18) 0.228(9) Uani 0.5 1 d . U P A -1
H36A H 0.557129 0.969759 0.437915 0.343 Uiso 0.5 1 calc R U P A -1
H36B H 0.574837 1.059170 0.377224 0.343 Uiso 0.5 1 calc R U P A -1
H36C H 0.607906 0.972414 0.334753 0.343 Uiso 0.5 1 calc R U P A -1


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O2 C5 1.206(2) . ?
O3 C7 1.333(2) . ?
O3 C8 1.438(3) . ?
O4 C7 1.200(2) . ?
O1 C5 1.333(2) . ?
O1 C6 1.447(2) . ?
C1 C11 1.512(3) . ?
C1 C21 1.518(2) . ?
C1 C2 1.563(3) . ?
C1 H1 1.0000 . ?
C7 C3 1.514(3) . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C11 C16 1.388(3) . ?
C11 C12 1.403(3) . ?
C12 C13 1.389(3) . ?
C12 C4 1.518(2) . ?
C13 C14 1.396(3) . ?
C13 H13 0.9500 . ?
C14 C15 1.389(4) . ?
C14 H14 0.9500 . ?
C15 C16 1.391(3) . ?
C15 H15 0.9500 . ?
C16 H16 0.9500 . ?
C21 C26 1.385(3) . ?
C21 C22 1.400(2) . ?
C22 C23 1.388(2) . ?
C22 C4 1.519(2) . ?
C23 C24 1.395(3) . ?
C23 H23 0.9500 . ?
C24 C25 1.385(3) . ?
C24 H24 0.9500 . ?
C25 C26 1.395(3) . ?
C25 H25 0.9500 . ?
C26 H26 0.9500 . ?
C2 C5 1.522(2) . ?
C2 C3 1.540(2) . ?
C2 H2 1.0000 . ?
C3 C4 1.562(2) . ?
C3 H3 1.0000 . ?
C4 H4 1.0000 . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C6 H6C 0.9800 . ?
N3 C31 1.3900 . ?
N3 C35 1.3900 . ?
C31 C36 1.311(16) . ?
C31 C32 1.3900 . ?
C32 C33 1.3900 . ?
C32 H32 0.9500 . ?
C33 C34 1.3900 . ?
C33 H33 0.9500 . ?
C34 C35 1.3900 . ?
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
C7 O3 C8 116.57(17) . . ?
C5 O1 C6 116.19(16) . . ?
C11 C1 C21 106.91(14) . . ?
C11 C1 C2 105.43(14) . . ?
C21 C1 C2 107.68(15) . . ?
C11 C1 H1 112.1 . . ?
C21 C1 H1 112.1 . . ?
C2 C1 H1 112.1 . . ?
O4 C7 O3 123.60(18) . . ?
O4 C7 C3 125.13(17) . . ?
O3 C7 C3 111.23(15) . . ?
O3 C8 H8A 109.5 . . ?
O3 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
O3 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C16 C11 C12 120.48(18) . . ?
C16 C11 C1 126.54(18) . . ?
C12 C11 C1 112.98(15) . . ?
C13 C12 C11 120.08(18) . . ?
C13 C12 C4 126.30(17) . . ?
C11 C12 C4 113.61(15) . . ?
C12 C13 C14 119.0(2) . . ?
C12 C13 H13 120.5 . . ?
C14 C13 H13 120.5 . . ?
C15 C14 C13 121.1(2) . . ?
C15 C14 H14 119.5 . . ?
C13 C14 H14 119.5 . . ?
C14 C15 C16 119.9(2) . . ?
C14 C15 H15 120.0 . . ?
C16 C15 H15 120.0 . . ?
C11 C16 C15 119.5(2) . . ?
C11 C16 H16 120.3 . . ?
C15 C16 H16 120.3 . . ?
C26 C21 C22 120.20(16) . . ?
C26 C21 C1 126.24(17) . . ?
C22 C21 C1 113.51(15) . . ?
C23 C22 C21 120.60(17) . . ?
C23 C22 C4 126.30(16) . . ?
C21 C22 C4 113.09(15) . . ?
C22 C23 C24 118.83(18) . . ?
C22 C23 H23 120.6 . . ?
C24 C23 H23 120.6 . . ?
C25 C24 C23 120.62(18) . . ?
C25 C24 H24 119.7 . . ?
C23 C24 H24 119.7 . . ?
C24 C25 C26 120.52(19) . . ?
C24 C25 H25 119.7 . . ?
C26 C25 H25 119.7 . . ?
C21 C26 C25 119.21(19) . . ?
C21 C26 H26 120.4 . . ?
C25 C26 H26 120.4 . . ?
C5 C2 C3 110.91(14) . . ?
C5 C2 C1 110.95(15) . . ?
C3 C2 C1 109.86(14) . . ?
C5 C2 H2 108.3 . . ?
C3 C2 H2 108.3 . . ?
C1 C2 H2 108.3 . . ?
C7 C3 C2 111.72(14) . . ?
C7 C3 C4 112.51(14) . . ?
C2 C3 C4 109.72(14) . . ?
C7 C3 H3 107.6 . . ?
C2 C3 H3 107.6 . . ?
C4 C3 H3 107.6 . . ?
C12 C4 C22 107.12(14) . . ?
C12 C4 C3 106.97(14) . . ?
C22 C4 C3 105.68(13) . . ?
C12 C4 H4 112.2 . . ?
C22 C4 H4 112.2 . . ?
C3 C4 H4 112.2 . . ?
O2 C5 O1 123.53(17) . . ?
O2 C5 C2 125.00(18) . . ?
O1 C5 C2 111.45(15) . . ?
O1 C6 H6A 109.5 . . ?
O1 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
O1 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
C31 N3 C35 120.0 . . ?
C36 C31 C32 123.7(11) . . ?
C36 C31 N3 113.4(11) . . ?
C32 C31 N3 120.0 . . ?
C31 C32 C33 120.0 . . ?
C31 C32 H32 120.0 . . ?
C33 C32 H32 120.0 . . ?
C34 C33 C32 120.0 . . ?
C34 C33 H33 120.0 . . ?
C32 C33 H33 120.0 . . ?
C33 C34 C35 120.0 . . ?
C33 C34 H34 120.0 . . ?
C35 C34 H34 120.0 . . ?
C34 C35 N3 120.0 . . ?
C34 C35 H35 120.0 . . ?
N3 C35 H35 120.0 . . ?
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
C8 O3 C7 O4 1.8(3) . . . . ?
C8 O3 C7 C3 -175.80(19) . . . . ?
C21 C1 C11 C16 -125.11(19) . . . . ?
C2 C1 C11 C16 120.49(19) . . . . ?
C21 C1 C11 C12 55.3(2) . . . . ?
C2 C1 C11 C12 -59.12(18) . . . . ?
C16 C11 C12 C13 0.2(3) . . . . ?
C1 C11 C12 C13 179.78(16) . . . . ?
C16 C11 C12 C4 179.06(16) . . . . ?
C1 C11 C12 C4 -1.3(2) . . . . ?
C11 C12 C13 C14 0.8(3) . . . . ?
C4 C12 C13 C14 -177.93(18) . . . . ?
C12 C13 C14 C15 -0.7(3) . . . . ?
C13 C14 C15 C16 -0.4(4) . . . . ?
C12 C11 C16 C15 -1.3(3) . . . . ?
C1 C11 C16 C15 179.17(19) . . . . ?
C14 C15 C16 C11 1.4(3) . . . . ?
C11 C1 C21 C26 123.0(2) . . . . ?
C2 C1 C21 C26 -124.1(2) . . . . ?
C11 C1 C21 C22 -54.6(2) . . . . ?
C2 C1 C21 C22 58.28(19) . . . . ?
C26 C21 C22 C23 1.3(3) . . . . ?
C1 C21 C22 C23 179.12(16) . . . . ?
C26 C21 C22 C4 -178.07(17) . . . . ?
C1 C21 C22 C4 -0.3(2) . . . . ?
C21 C22 C23 C24 -1.4(3) . . . . ?
C4 C22 C23 C24 177.93(18) . . . . ?
C22 C23 C24 C25 0.4(3) . . . . ?
C23 C24 C25 C26 0.6(4) . . . . ?
C22 C21 C26 C25 -0.3(3) . . . . ?
C1 C21 C26 C25 -177.77(19) . . . . ?
C24 C25 C26 C21 -0.7(3) . . . . ?
C11 C1 C2 C5 -62.14(18) . . . . ?
C21 C1 C2 C5 -176.01(14) . . . . ?
C11 C1 C2 C3 60.86(17) . . . . ?
C21 C1 C2 C3 -53.01(18) . . . . ?
O4 C7 C3 C2 15.5(3) . . . . ?
O3 C7 C3 C2 -166.96(15) . . . . ?
O4 C7 C3 C4 139.4(2) . . . . ?
O3 C7 C3 C4 -43.0(2) . . . . ?
C5 C2 C3 C7 -116.44(17) . . . . ?
C1 C2 C3 C7 120.54(16) . . . . ?
C5 C2 C3 C4 118.07(15) . . . . ?
C1 C2 C3 C4 -4.95(18) . . . . ?
C13 C12 C4 C22 125.33(19) . . . . ?
C11 C12 C4 C22 -53.50(19) . . . . ?
C13 C12 C4 C3 -121.74(19) . . . . ?
C11 C12 C4 C3 59.44(18) . . . . ?
C23 C22 C4 C12 -125.17(19) . . . . ?
C21 C22 C4 C12 54.19(19) . . . . ?
C23 C22 C4 C3 121.02(19) . . . . ?
C21 C22 C4 C3 -59.61(19) . . . . ?
C7 C3 C4 C12 -178.38(14) . . . . ?
C2 C3 C4 C12 -53.34(17) . . . . ?
C7 C3 C4 C22 -64.47(18) . . . . ?
C2 C3 C4 C22 60.56(17) . . . . ?
C6 O1 C5 O2 -2.5(3) . . . . ?
C6 O1 C5 C2 178.67(16) . . . . ?
C3 C2 C5 O2 8.7(3) . . . . ?
C1 C2 C5 O2 131.1(2) . . . . ?
C3 C2 C5 O1 -172.42(14) . . . . ?
C1 C2 C5 O1 -50.03(19) . . . . ?
C35 N3 C31 C36 -161.4(13) . . . . ?
C35 N3 C31 C32 0.0 . . . . ?
C36 C31 C32 C33 159.4(15) . . . . ?
N3 C31 C32 C33 0.0 . . . . ?
C31 C32 C33 C34 0.0 . . . . ?
C32 C33 C34 C35 0.0 . . . . ?
C33 C34 C35 N3 0.0 . . . . ?
C31 N3 C35 C34 0.0 . . . . ?

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
C2 H2 O4 1.00 2.32 2.828(3) 110 . yes
C2 H2 O3 1.00 2.59 3.445(2) 144 7_565 yes
C3 H3 O2 1.00 2.26 2.805(2) 113 . yes
C13 H13 O2 0.95 2.58 3.419(3) 148 7_566 yes

_refine_diff_density_max         0.697
_refine_diff_density_min         -0.610
_refine_diff_density_rms         0.077


_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_ma150
_database_code_depnum_ccdc_archive 'CCDC 2236050'
loop_
_audit_author_name
_audit_author_address
'Eric Hosten'
;Nelson Mandela University
South Africa
;
_audit_update_record             
;
2023-01-13 deposited with the CCDC.	2023-02-28 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        
trans-α,α,α',α'-tetra(p-chlorophenyl)-9,10-dihydro-9,10-ethanoanthracene-11,12-dimethanol
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C42 H30 Cl4 O2, C6 H7 N'
_chemical_formula_sum            'C48 H37 Cl4 N O2'
_chemical_formula_weight         801.58

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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           70
_space_group_name_H-M_alt        'F d d d'
_space_group_name_Hall           '-F 2uv 2vw'

_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+3/4, -y+3/4, z'
'-x+3/4, y, -z+3/4'
'x, -y+3/4, -z+3/4'
'x, y+1/2, z+1/2'
'-x+3/4, -y+5/4, z+1/2'
'-x+3/4, y+1/2, -z+5/4'
'x, -y+5/4, -z+5/4'
'x+1/2, y, z+1/2'
'-x+5/4, -y+3/4, z+1/2'
'-x+5/4, y, -z+5/4'
'x+1/2, -y+3/4, -z+5/4'
'x+1/2, y+1/2, z'
'-x+5/4, -y+5/4, z'
'-x+5/4, y+1/2, -z+3/4'
'x+1/2, -y+5/4, -z+3/4'
'-x, -y, -z'
'x-3/4, y-3/4, -z'
'x-3/4, -y, z-3/4'
'-x, y-3/4, z-3/4'
'-x, -y+1/2, -z+1/2'
'x-3/4, y-1/4, -z+1/2'
'x-3/4, -y+1/2, z-1/4'
'-x, y-1/4, z-1/4'
'-x+1/2, -y, -z+1/2'
'x-1/4, y-3/4, -z+1/2'
'x-1/4, -y, z-1/4'
'-x+1/2, y-3/4, z-1/4'
'-x+1/2, -y+1/2, -z'
'x-1/4, y-1/4, -z'
'x-1/4, -y+1/2, z-3/4'
'-x+1/2, y-1/4, z-3/4'

_cell_length_a                   15.7544(7)
_cell_length_b                   25.0313(11)
_cell_length_c                   40.1189(16)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     15821.0(12)
_cell_formula_units_Z            16
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    9958
_cell_measurement_theta_min      2.78
_cell_measurement_theta_max      28.32

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.346
_exptl_crystal_F_000             6656
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.579
_exptl_crystal_size_mid          0.143
_exptl_crystal_size_min          0.078
_exptl_absorpt_coefficient_mu    0.341
_shelx_estimated_absorpt_T_min   0.827
_shelx_estimated_absorpt_T_max   0.974
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_correction_T_min  0.7955
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_process_details   'SADABS-2008/1 (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            54065
_diffrn_reflns_av_unetI/netI     0.0430
_diffrn_reflns_av_R_equivalents  0.0752
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_k_min       -32
_diffrn_reflns_limit_k_max       33
_diffrn_reflns_limit_l_min       -53
_diffrn_reflns_limit_l_max       53
_diffrn_reflns_theta_min         1.609
_diffrn_reflns_theta_max         28.401
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             4939
_reflns_number_gt                3154
_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 disordered methyl groups were placed in calculated positions
and were included in the refinement in the riding model approximation, with
Uiso(H) set to 1.5 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).

The 4-methylpyridine solvent/guest molecule is extensively disordered around a
2-fold rotational axis. Residual electron density indicates that the solvent has
additional disorder orientations but attempts to include them were unsuccessful.
The disorder necessitated the use of various restraints and constraints: RIGU,
ISOR, SADI and DFIX. The benzene ring was was forced into a regular hexagon with
bond lengths 1.39 Å (AFIX 66 in the SHELXL program (Sheldrick, 2015)).,Solvent disorder
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0950P)²+42.9522P] 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     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4939
_refine_ls_number_parameters     269
_refine_ls_number_restraints     89
_refine_ls_R_factor_all          0.0971
_refine_ls_R_factor_gt           0.0594
_refine_ls_wR_factor_ref         0.1968
_refine_ls_wR_factor_gt          0.1615
_refine_ls_goodness_of_fit_ref   1.016
_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
Cl1 Cl 0.41832(7) 0.44375(4) 0.50047(2) 0.0754(3) Uani 1 1 d . . . . .
Cl2 Cl 0.46552(7) 0.67488(3) 0.67253(2) 0.0748(3) Uani 1 1 d . . . . .
O1 O 0.52380(10) 0.41158(7) 0.65796(4) 0.0446(4) Uani 1 1 d . . . . .
H1 H 0.530178 0.409485 0.678204 0.067 Uiso 1 1 calc R U . . .
C1 C 0.44327(14) 0.43583(9) 0.65080(6) 0.0366(5) Uani 1 1 d . . . . .
C2 C 0.37070(15) 0.40630(9) 0.67033(5) 0.0386(5) Uani 1 1 d . . . . .
H2 H 0.316757 0.415277 0.659532 0.046 Uiso 1 1 calc R U . . .
C3 C 0.36566(19) 0.42615(11) 0.70756(6) 0.0507(7) Uani 1 1 d . . . . .
H3 H 0.357984 0.464950 0.708781 0.061 Uiso 1 1 calc R U . . .
C11 C 0.43451(15) 0.43359(9) 0.61278(6) 0.0371(5) Uani 1 1 d . . . . .
C12 C 0.50663(17) 0.43066(11) 0.59309(6) 0.0476(6) Uani 1 1 d . . . . .
H12 H 0.559322 0.426254 0.603174 0.057 Uiso 1 1 calc R U . . .
C13 C 0.5017(2) 0.43417(12) 0.55865(7) 0.0546(7) Uani 1 1 d . . . . .
H13 H 0.550778 0.432271 0.545795 0.066 Uiso 1 1 calc R U . . .
C14 C 0.42458(19) 0.44042(10) 0.54374(6) 0.0490(6) Uani 1 1 d . . . . .
C15 C 0.35132(18) 0.44379(11) 0.56236(7) 0.0487(6) Uani 1 1 d . . . . .
H15 H 0.299031 0.448238 0.551966 0.058 Uiso 1 1 calc R U . . .
C16 C 0.35649(16) 0.44047(10) 0.59675(6) 0.0427(5) Uani 1 1 d . . . . .
H16 H 0.307183 0.442857 0.609408 0.051 Uiso 1 1 calc R U . . .
C21 C 0.44687(16) 0.49579(9) 0.65900(6) 0.0397(5) Uani 1 1 d . . . . .
C22 C 0.37531(18) 0.52797(10) 0.65700(7) 0.0491(6) Uani 1 1 d . . . . .
H22 H 0.322998 0.512441 0.652365 0.059 Uiso 1 1 calc R U . . .
C23 C 0.3801(2) 0.58286(11) 0.66176(7) 0.0533(7) Uani 1 1 d . . . . .
H23 H 0.331352 0.603794 0.660742 0.064 Uiso 1 1 calc R U . . .
C24 C 0.4578(2) 0.60583(11) 0.66800(6) 0.0539(7) Uani 1 1 d . . . . .
C25 C 0.5291(2) 0.57490(13) 0.67063(9) 0.0679(9) Uani 1 1 d . . . . .
H25 H 0.581031 0.590511 0.675727 0.081 Uiso 1 1 calc R U . . .
C26 C 0.52359(19) 0.52049(12) 0.66568(8) 0.0575(7) Uani 1 1 d . . . . .
H26 H 0.572637 0.499902 0.666872 0.069 Uiso 1 1 calc R U . . .
C31 C 0.44540(19) 0.40877(13) 0.72511(6) 0.0553(7) Uani 1 1 d . . . . .
C32 C 0.45727(19) 0.35336(13) 0.72423(6) 0.0556(7) Uani 1 1 d . . . . .
C33 C 0.5290(2) 0.33050(15) 0.73802(8) 0.0684(9) Uani 1 1 d . . . . .
H33 H 0.537382 0.293741 0.737311 0.082 Uiso 1 1 calc R U . . .
C34 C 0.5889(2) 0.3643(2) 0.75314(8) 0.0840(13) Uani 1 1 d . . . . .
H34 H 0.637728 0.349549 0.762407 0.101 Uiso 1 1 calc R U . . .
C35 C 0.5770(3) 0.41830(18) 0.75451(8) 0.0818(12) Uani 1 1 d . . . . .
H35 H 0.617246 0.439784 0.764917 0.098 Uiso 1 1 calc R U . . .
C36 C 0.5055(2) 0.44125(15) 0.74052(7) 0.0690(10) Uani 1 1 d . . . . .
H36 H 0.497659 0.478048 0.741402 0.083 Uiso 1 1 calc R U . . .
N5 N 0.1291(10) 0.4911(6) 0.5803(3) 0.237(7) Uani 0.5 1 d G U P A -1
C51 C 0.131(2) 0.5452(6) 0.5881(3) 0.247(11) Uani 0.5 1 d G U P A -1
H51 H 0.133185 0.570557 0.571211 0.297 Uiso 0.5 1 calc R U P A -1
C52 C 0.130(2) 0.5613(3) 0.6213(4) 0.175(5) Uani 0.5 1 d DG U P A -1
H52 H 0.130896 0.597518 0.626531 0.209 Uiso 0.5 1 calc R U P A -1
C53 C 0.1264(10) 0.5234(4) 0.6466(3) 0.157(5) Uani 0.5 1 d DG U P A -1
C54 C 0.1245(17) 0.4694(3) 0.6387(4) 0.179(6) Uani 0.5 1 d DG U P A -1
H54 H 0.122293 0.443992 0.655605 0.215 Uiso 0.5 1 calc R U P A -1
C55 C 0.1258(19) 0.4532(4) 0.6055(4) 0.228(8) Uani 0.5 1 d G U P A -1
H55 H 0.124582 0.417030 0.600285 0.274 Uiso 0.5 1 calc R U P A -1
C56 C 0.116(2) 0.5435(7) 0.6810(5) 0.257(11) Uani 0.5 1 d D U P A -1
H56A H 0.114744 0.513948 0.696163 0.386 Uiso 0.5 1 calc R U P A -1
H56B H 0.163009 0.566444 0.686423 0.386 Uiso 0.5 1 calc R U P A -1
H56C H 0.064102 0.563293 0.682615 0.386 Uiso 0.5 1 calc R U P A -1


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cl1 C14 1.741(3) . ?
Cl2 C24 1.742(3) . ?
O1 C1 1.436(3) . ?
O1 H1 0.8200 . ?
C1 C11 1.533(3) . ?
C1 C21 1.537(3) . ?
C1 C2 1.571(3) . ?
C2 C2 1.573(5) 2 ?
C2 C3 1.576(3) . ?
C2 H2 0.9800 . ?
C3 C31 1.504(4) . ?
C3 C32 1.521(4) 2 ?
C3 H3 0.9800 . ?
C11 C12 1.386(3) . ?
C11 C16 1.398(3) . ?
C12 C13 1.387(4) . ?
C12 H12 0.9300 . ?
C13 C14 1.364(4) . ?
C13 H13 0.9300 . ?
C14 C15 1.378(4) . ?
C15 C16 1.384(4) . ?
C15 H15 0.9300 . ?
C16 H16 0.9300 . ?
C21 C26 1.384(4) . ?
C21 C22 1.388(4) . ?
C22 C23 1.389(4) . ?
C22 H22 0.9300 . ?
C23 C24 1.376(4) . ?
C23 H23 0.9300 . ?
C24 C25 1.368(5) . ?
C25 C26 1.379(4) . ?
C25 H25 0.9300 . ?
C26 H26 0.9300 . ?
C31 C36 1.393(4) . ?
C31 C32 1.400(4) . ?
C32 C33 1.382(5) . ?
C33 C34 1.405(5) . ?
C33 H33 0.9300 . ?
C34 C35 1.367(6) . ?
C34 H34 0.9300 . ?
C35 C36 1.383(6) . ?
C35 H35 0.9300 . ?
C36 H36 0.9300 . ?
N5 C51 1.3900 . ?
N5 C55 1.3900 . ?
C51 C52 1.3900 . ?
C51 H51 0.9300 . ?
C52 C53 1.3900 . ?
C52 H52 0.9300 . ?
C53 C54 1.3900 . ?
C53 C56 1.478(16) . ?
C54 C55 1.3900 . ?
C54 H54 0.9300 . ?
C55 H55 0.9300 . ?
C56 H56A 0.9600 . ?
C56 H56B 0.9600 . ?
C56 H56C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 O1 H1 109.5 . . ?
O1 C1 C11 105.26(18) . . ?
O1 C1 C21 109.72(18) . . ?
C11 C1 C21 104.59(18) . . ?
O1 C1 C2 110.16(18) . . ?
C11 C1 C2 114.44(18) . . ?
C21 C1 C2 112.30(19) . . ?
C1 C2 C2 114.0(2) . 2 ?
C1 C2 C3 111.17(18) . . ?
C2 C2 C3 108.57(14) 2 . ?
C1 C2 H2 107.6 . . ?
C2 C2 H2 107.6 2 . ?
C3 C2 H2 107.6 . . ?
C31 C3 C32 106.5(2) . 2 ?
C31 C3 C2 108.1(2) . . ?
C32 C3 C2 107.58(19) 2 . ?
C31 C3 H3 111.5 . . ?
C32 C3 H3 111.5 2 . ?
C2 C3 H3 111.5 . . ?
C12 C11 C16 117.7(2) . . ?
C12 C11 C1 119.7(2) . . ?
C16 C11 C1 122.2(2) . . ?
C11 C12 C13 121.3(3) . . ?
C11 C12 H12 119.4 . . ?
C13 C12 H12 119.4 . . ?
C14 C13 C12 119.6(3) . . ?
C14 C13 H13 120.2 . . ?
C12 C13 H13 120.2 . . ?
C13 C14 C15 121.1(2) . . ?
C13 C14 Cl1 119.6(2) . . ?
C15 C14 Cl1 119.4(2) . . ?
C14 C15 C16 119.2(2) . . ?
C14 C15 H15 120.4 . . ?
C16 C15 H15 120.4 . . ?
C15 C16 C11 121.2(2) . . ?
C15 C16 H16 119.4 . . ?
C11 C16 H16 119.4 . . ?
C26 C21 C22 117.5(2) . . ?
C26 C21 C1 120.7(2) . . ?
C22 C21 C1 121.6(2) . . ?
C21 C22 C23 121.5(3) . . ?
C21 C22 H22 119.3 . . ?
C23 C22 H22 119.3 . . ?
C24 C23 C22 119.1(3) . . ?
C24 C23 H23 120.5 . . ?
C22 C23 H23 120.5 . . ?
C25 C24 C23 120.5(3) . . ?
C25 C24 Cl2 119.7(2) . . ?
C23 C24 Cl2 119.7(3) . . ?
C24 C25 C26 119.8(3) . . ?
C24 C25 H25 120.1 . . ?
C26 C25 H25 120.1 . . ?
C25 C26 C21 121.6(3) . . ?
C25 C26 H26 119.2 . . ?
C21 C26 H26 119.2 . . ?
C36 C31 C32 119.9(3) . . ?
C36 C31 C3 127.4(3) . . ?
C32 C31 C3 112.7(2) . . ?
C33 C32 C31 120.6(3) . . ?
C33 C32 C3 126.3(3) . 2 ?
C31 C32 C3 113.0(3) . 2 ?
C32 C33 C34 118.2(4) . . ?
C32 C33 H33 120.9 . . ?
C34 C33 H33 120.9 . . ?
C35 C34 C33 121.4(4) . . ?
C35 C34 H34 119.3 . . ?
C33 C34 H34 119.3 . . ?
C34 C35 C36 120.4(3) . . ?
C34 C35 H35 119.8 . . ?
C36 C35 H35 119.8 . . ?
C35 C36 C31 119.4(4) . . ?
C35 C36 H36 120.3 . . ?
C31 C36 H36 120.3 . . ?
C51 N5 C55 120.0 . . ?
C52 C51 N5 120.0 . . ?
C52 C51 H51 120.0 . . ?
N5 C51 H51 120.0 . . ?
C51 C52 C53 120.0 . . ?
C51 C52 H52 120.0 . . ?
C53 C52 H52 120.0 . . ?
C52 C53 C54 120.0 . . ?
C52 C53 C56 116.9(7) . . ?
C54 C53 C56 122.8(7) . . ?
C53 C54 C55 120.0 . . ?
C53 C54 H54 120.0 . . ?
C55 C54 H54 120.0 . . ?
C54 C55 N5 120.0 . . ?
C54 C55 H55 120.0 . . ?
N5 C55 H55 120.0 . . ?
C53 C56 H56A 109.5 . . ?
C53 C56 H56B 109.5 . . ?
H56A C56 H56B 109.5 . . ?
C53 C56 H56C 109.5 . . ?
H56A C56 H56C 109.5 . . ?
H56B C56 H56C 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
O1 C1 C2 C2 -42.0(2) . . . 2 ?
C11 C1 C2 C2 76.3(2) . . . 2 ?
C21 C1 C2 C2 -164.64(17) . . . 2 ?
O1 C1 C2 C3 81.1(2) . . . . ?
C11 C1 C2 C3 -160.6(2) . . . . ?
C21 C1 C2 C3 -41.6(3) . . . . ?
C1 C2 C3 C31 -66.7(3) . . . . ?
C2 C2 C3 C31 59.4(3) 2 . . . ?
C1 C2 C3 C32 178.6(2) . . . 2 ?
C2 C2 C3 C32 -55.3(3) 2 . . 2 ?
O1 C1 C11 C12 -24.3(3) . . . . ?
C21 C1 C11 C12 91.3(3) . . . . ?
C2 C1 C11 C12 -145.4(2) . . . . ?
O1 C1 C11 C16 163.0(2) . . . . ?
C21 C1 C11 C16 -81.3(3) . . . . ?
C2 C1 C11 C16 42.0(3) . . . . ?
C16 C11 C12 C13 -0.3(4) . . . . ?
C1 C11 C12 C13 -173.2(2) . . . . ?
C11 C12 C13 C14 -0.3(4) . . . . ?
C12 C13 C14 C15 0.6(4) . . . . ?
C12 C13 C14 Cl1 -179.0(2) . . . . ?
C13 C14 C15 C16 -0.3(4) . . . . ?
Cl1 C14 C15 C16 179.2(2) . . . . ?
C14 C15 C16 C11 -0.2(4) . . . . ?
C12 C11 C16 C15 0.5(4) . . . . ?
C1 C11 C16 C15 173.3(2) . . . . ?
O1 C1 C21 C26 11.4(3) . . . . ?
C11 C1 C21 C26 -101.0(3) . . . . ?
C2 C1 C21 C26 134.3(2) . . . . ?
O1 C1 C21 C22 -174.6(2) . . . . ?
C11 C1 C21 C22 73.0(3) . . . . ?
C2 C1 C21 C22 -51.7(3) . . . . ?
C26 C21 C22 C23 -0.5(4) . . . . ?
C1 C21 C22 C23 -174.7(2) . . . . ?
C21 C22 C23 C24 1.2(4) . . . . ?
C22 C23 C24 C25 -2.2(4) . . . . ?
C22 C23 C24 Cl2 177.7(2) . . . . ?
C23 C24 C25 C26 2.6(5) . . . . ?
Cl2 C24 C25 C26 -177.3(3) . . . . ?
C24 C25 C26 C21 -1.9(5) . . . . ?
C22 C21 C26 C25 0.8(4) . . . . ?
C1 C21 C26 C25 175.1(3) . . . . ?
C32 C3 C31 C36 -124.3(3) 2 . . . ?
C2 C3 C31 C36 120.4(3) . . . . ?
C32 C3 C31 C32 57.2(3) 2 . . . ?
C2 C3 C31 C32 -58.2(3) . . . . ?
C36 C31 C32 C33 -1.2(4) . . . . ?
C3 C31 C32 C33 177.5(3) . . . . ?
C36 C31 C32 C3 178.0(2) . . . 2 ?
C3 C31 C32 C3 -3.3(3) . . . 2 ?
C31 C32 C33 C34 0.6(4) . . . . ?
C3 C32 C33 C34 -178.5(3) 2 . . . ?
C32 C33 C34 C35 0.4(5) . . . . ?
C33 C34 C35 C36 -0.9(5) . . . . ?
C34 C35 C36 C31 0.3(5) . . . . ?
C32 C31 C36 C35 0.7(4) . . . . ?
C3 C31 C36 C35 -177.7(3) . . . . ?
C55 N5 C51 C52 0.0 . . . . ?
N5 C51 C52 C53 0.0 . . . . ?
C51 C52 C53 C54 0.0 . . . . ?
C51 C52 C53 C56 -174(2) . . . . ?
C52 C53 C54 C55 0.0 . . . . ?
C56 C53 C54 C55 174(2) . . . . ?
C53 C54 C55 N5 0.0 . . . . ?
C51 N5 C55 C54 0.0 . . . . ?

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
C2 H2 O1 0.98 2.40 2.884(3) 110 2 yes
C12 H12 O1 0.93 2.30 2.660(3) 103 . yes
C26 H26 O1 0.93 2.37 2.744(3) 104 . yes
C55 H55 O1 0.93 2.55 3.337(16) 143 12_455 yes

_refine_diff_density_max         0.852
_refine_diff_density_min         -0.520
_refine_diff_density_rms         0.070


_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_ma047
_database_code_depnum_ccdc_archive 'CCDC 2236046'
loop_
_audit_author_name
_audit_author_address
'Eric Hosten'
;Nelson Mandela University
South Africa
;
_audit_update_record             
;
2023-01-13 deposited with the CCDC.	2023-02-28 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        
'trans-dimethyl 9,10-dihydro-9,10- ethanoanthracene-11,12-dicarboxylate'
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         '2(C20 H18 O4), C6 H7 N'
_chemical_formula_sum            'C46 H43 N O8'
_chemical_formula_weight         737.81

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                   11.2912(6)
_cell_length_b                   21.2529(13)
_cell_length_c                   15.8162(10)
_cell_angle_alpha                90
_cell_angle_beta                 90.136(3)
_cell_angle_gamma                90
_cell_volume                     3795.4(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    200(2)
_cell_measurement_reflns_used    9162
_cell_measurement_theta_min      2.41
_cell_measurement_theta_max      28.34

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.291
_exptl_crystal_F_000             1560
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.636
_exptl_crystal_size_mid          0.504
_exptl_crystal_size_min          0.402
_exptl_absorpt_coefficient_mu    0.088
_shelx_estimated_absorpt_T_min   0.946
_shelx_estimated_absorpt_T_max   0.965
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_correction_T_min  0.9060
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_process_details   'SADABS-2008/1 (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            96013
_diffrn_reflns_av_unetI/netI     0.0116
_diffrn_reflns_av_R_equivalents  0.0204
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -28
_diffrn_reflns_limit_k_max       28
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         0.958
_diffrn_reflns_theta_max         28.344
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             9440
_reflns_number_gt                8453
_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. Completness statistics refer to single and
 composite reflections containing twin component 1 only.
;

_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 non-disordered 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
1.5 Ueq(C). The H atoms of the disordered methyl groups were placed in
calculated positions (HFIX 33).

The 3-methylpyridine solvent/guest molecule has extensively positional
disordered. Two disorder orientations are modelled but residual electron density
indicates that the solvent has additional disorder orientations and attempts to
include them were unsuccessful. The disorder necessitated the use of various
restraints and constraints: RIGU, ISOR, EXYZ and SAME. The benzene ring was was
forced into a regular hexagon with bond lengths 1.39 Å (AFIX 66 in the SHELXL
program (Sheldrick, 2015)).

Two reflections with large differences between their observed and calculated
intensities were omitted. This is due to obstruction by the beam stop.

Refined as a 2-component twin.,Twin,Solvent disorder
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0971P)²+1.6172P] 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     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         9440
_refine_ls_number_parameters     538
_refine_ls_number_restraints     189
_refine_ls_R_factor_all          0.0636
_refine_ls_R_factor_gt           0.0552
_refine_ls_wR_factor_ref         0.1648
_refine_ls_wR_factor_gt          0.1512
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_restrained_S_all      1.084
_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
O11 O -0.04749(13) 0.26280(8) 0.56544(10) 0.0405(4) Uani 1 1 d . . . . .
O12 O 0.14769(15) 0.27546(10) 0.57373(15) 0.0622(6) Uani 1 1 d . . . . .
O13 O 0.34658(13) 0.11339(7) 0.43028(11) 0.0372(3) Uani 1 1 d . . . . .
O14 O 0.19946(15) 0.08550(8) 0.51568(12) 0.0475(4) Uani 1 1 d . . . . .
O21 O 0.45692(14) 0.23045(7) -0.03797(11) 0.0406(4) Uani 1 1 d . . . . .
O22 O 0.65251(16) 0.21593(9) -0.03469(13) 0.0529(5) Uani 1 1 d . . . . .
O23 O 0.84511(13) 0.38969(7) 0.09054(11) 0.0378(3) Uani 1 1 d . . . . .
O24 O 0.70280(15) 0.40942(8) -0.00461(11) 0.0455(4) Uani 1 1 d . . . . .
C11 C -0.02769(16) 0.20046(8) 0.41119(12) 0.0265(3) Uani 1 1 d . . . . .
H11 H -0.110010 0.203593 0.433986 0.032 Uiso 1 1 calc R U . . .
C12 C 0.06695(16) 0.19443(8) 0.48348(12) 0.0263(3) Uani 1 1 d . . . . .
H12 H 0.048625 0.155342 0.516114 0.032 Uiso 1 1 calc R U . . .
C13 C 0.19040(16) 0.18626(8) 0.44443(12) 0.0266(3) Uani 1 1 d . . . . .
H13 H 0.243459 0.220278 0.466264 0.032 Uiso 1 1 calc R U . . .
C14 C 0.18186(16) 0.19200(8) 0.34545(12) 0.0284(4) Uani 1 1 d . . . . .
H14 H 0.261227 0.189226 0.317784 0.034 Uiso 1 1 calc R U . . .
C15 C 0.06289(18) 0.24915(10) 0.54452(13) 0.0325(4) Uani 1 1 d . . . . .
C16 C -0.0637(3) 0.31141(14) 0.6274(2) 0.0605(8) Uani 1 1 d . . . . .
H16A H -0.023248 0.349762 0.608831 0.091 Uiso 1 1 calc R U . . .
H16B H -0.030571 0.297631 0.681644 0.091 Uiso 1 1 calc R U . . .
H16C H -0.148483 0.320002 0.634026 0.091 Uiso 1 1 calc R U . . .
C17 C 0.24287(17) 0.12271(9) 0.46840(13) 0.0301(4) Uani 1 1 d . . . . .
C18 C 0.4033(2) 0.05320(10) 0.44530(16) 0.0410(5) Uani 1 1 d . . . . .
H18A H 0.360352 0.020178 0.414716 0.061 Uiso 1 1 calc R U . . .
H18B H 0.402494 0.043903 0.505983 0.061 Uiso 1 1 calc R U . . .
H18C H 0.485328 0.054839 0.425345 0.061 Uiso 1 1 calc R U . . .
C21 C 0.47208(16) 0.30187(8) 0.11144(12) 0.0266(3) Uani 1 1 d . . . . .
H21 H 0.390310 0.296886 0.087951 0.032 Uiso 1 1 calc R U . . .
C22 C 0.56829(16) 0.30399(8) 0.04048(12) 0.0264(3) Uani 1 1 d . . . . .
H22 H 0.550355 0.340693 0.003015 0.032 Uiso 1 1 calc R U . . .
C23 C 0.69076(16) 0.31515(8) 0.08119(12) 0.0271(3) Uani 1 1 d . . . . .
H23 H 0.744377 0.279908 0.064235 0.033 Uiso 1 1 calc R U . . .
C24 C 0.68041(16) 0.31532(9) 0.17984(12) 0.0292(4) Uani 1 1 d . . . . .
H24 H 0.759226 0.320210 0.208062 0.035 Uiso 1 1 calc R U . . .
C25 C 0.56714(17) 0.24513(10) -0.01365(12) 0.0313(4) Uani 1 1 d . . . . .
C26 C 0.4460(3) 0.17677(13) -0.09389(19) 0.0565(7) Uani 1 1 d . . . . .
H26A H 0.362055 0.168898 -0.105832 0.085 Uiso 1 1 calc R U . . .
H26B H 0.480764 0.139640 -0.066766 0.085 Uiso 1 1 calc R U . . .
H26C H 0.487647 0.185465 -0.146893 0.085 Uiso 1 1 calc R U . . .
C27 C 0.74416(16) 0.37660(9) 0.05007(13) 0.0299(4) Uani 1 1 d . . . . .
C28 C 0.9025(2) 0.44812(10) 0.06812(16) 0.0415(5) Uani 1 1 d . . . . .
H28A H 0.905898 0.451892 0.006418 0.062 Uiso 1 1 calc R U . . .
H28B H 0.983063 0.448591 0.091305 0.062 Uiso 1 1 calc R U . . .
H28C H 0.857468 0.483486 0.091426 0.062 Uiso 1 1 calc R U . . .
C111 C -0.01248(17) 0.14378(8) 0.35385(12) 0.0283(4) Uani 1 1 d . . . . .
C112 C 0.09987(18) 0.13964(8) 0.31765(12) 0.0295(4) Uani 1 1 d . . . . .
C113 C 0.1275(2) 0.09054(10) 0.26422(14) 0.0378(4) Uani 1 1 d . . . . .
H113 H 0.204730 0.087132 0.240968 0.045 Uiso 1 1 calc R U . . .
C114 C 0.0413(2) 0.04601(10) 0.24462(16) 0.0464(5) Uani 1 1 d . . . . .
H114 H 0.059089 0.012703 0.206646 0.056 Uiso 1 1 calc R U . . .
C115 C -0.0698(2) 0.05012(10) 0.28021(16) 0.0445(5) Uani 1 1 d . . . . .
H115 H -0.127973 0.019405 0.266716 0.053 Uiso 1 1 calc R U . . .
C116 C -0.0977(2) 0.09864(10) 0.33557(14) 0.0359(4) Uani 1 1 d . . . . .
H116 H -0.174018 0.100909 0.360559 0.043 Uiso 1 1 calc R U . . .
C121 C 0.00600(16) 0.25762(8) 0.36039(12) 0.0273(3) Uani 1 1 d . . . . .
C122 C 0.11921(16) 0.25317(9) 0.32545(13) 0.0291(4) Uani 1 1 d . . . . .
C123 C 0.16267(19) 0.30114(10) 0.27472(14) 0.0370(4) Uani 1 1 d . . . . .
H123 H 0.239484 0.298244 0.250659 0.044 Uiso 1 1 calc R U . . .
C124 C 0.0914(2) 0.35391(10) 0.25958(17) 0.0451(5) Uani 1 1 d . . . . .
H124 H 0.119500 0.386720 0.224116 0.054 Uiso 1 1 calc R U . . .
C125 C -0.0188(2) 0.35865(10) 0.29551(17) 0.0442(5) Uani 1 1 d . . . . .
H125 H -0.065618 0.395033 0.285388 0.053 Uiso 1 1 calc R U . . .
C126 C -0.06291(19) 0.31064(9) 0.34675(14) 0.0354(4) Uani 1 1 d . . . . .
H126 H -0.138944 0.314238 0.371880 0.042 Uiso 1 1 calc R U . . .
C211 C 0.50638(16) 0.24797(9) 0.16939(12) 0.0280(3) Uani 1 1 d . . . . .
C212 C 0.61881(16) 0.25524(9) 0.20572(12) 0.0287(4) Uani 1 1 d . . . . .
C213 C 0.66120(19) 0.21109(10) 0.26299(14) 0.0360(4) Uani 1 1 d . . . . .
H213 H 0.737300 0.215921 0.287909 0.043 Uiso 1 1 calc R U . . .
C214 C 0.5905(2) 0.15966(10) 0.28334(16) 0.0421(5) Uani 1 1 d . . . . .
H214 H 0.617839 0.129627 0.323368 0.050 Uiso 1 1 calc R U . . .
C215 C 0.4806(2) 0.15193(10) 0.24571(16) 0.0406(5) Uani 1 1 d . . . . .
H215 H 0.433922 0.116194 0.259412 0.049 Uiso 1 1 calc R U . . .
C216 C 0.43755(18) 0.19622(9) 0.18762(13) 0.0333(4) Uani 1 1 d . . . . .
H216 H 0.362503 0.190667 0.161391 0.040 Uiso 1 1 calc R U . . .
C221 C 0.48565(17) 0.36204(9) 0.16267(12) 0.0299(4) Uani 1 1 d . . . . .
C222 C 0.59768(18) 0.36899(9) 0.20019(12) 0.0305(4) Uani 1 1 d . . . . .
C223 C 0.6235(2) 0.42124(10) 0.24955(14) 0.0389(4) Uani 1 1 d . . . . .
H223 H 0.699546 0.426023 0.274523 0.047 Uiso 1 1 calc R U . . .
C224 C 0.5360(3) 0.46659(11) 0.26190(17) 0.0494(6) Uani 1 1 d . . . . .
H224 H 0.552173 0.502383 0.296001 0.059 Uiso 1 1 calc R U . . .
C225 C 0.4258(2) 0.45968(11) 0.22472(17) 0.0490(6) Uani 1 1 d . . . . .
H225 H 0.366999 0.490960 0.233518 0.059 Uiso 1 1 calc R U . . .
C226 C 0.3996(2) 0.40762(10) 0.17459(14) 0.0377(4) Uani 1 1 d . . . . .
H226 H 0.323825 0.403424 0.148948 0.045 Uiso 1 1 calc R U . . .
C31 C 0.2912(5) 0.5221(2) 0.4579(3) 0.0589(17) Uani 0.569(7) 1 d DG U P A 1
C32 C 0.3455(5) 0.5098(2) 0.5351(3) 0.096(2) Uani 0.569(7) 1 d DG U P A 1
H32 H 0.405328 0.537202 0.555844 0.115 Uiso 0.569(7) 1 calc R U P A 1
N3 N 0.3121(6) 0.4574(3) 0.5820(3) 0.106(2) Uani 0.569(7) 1 d DG U P A 1
C33 C 0.2245(5) 0.4174(2) 0.5517(3) 0.0716(17) Uani 0.569(7) 1 d DG U P A 1
H33 H 0.201674 0.381574 0.583714 0.086 Uiso 0.569(7) 1 calc R U P A 1
C34 C 0.1702(5) 0.4297(3) 0.4744(4) 0.126(4) Uani 0.569(7) 1 d DG U P A 1
H34 H 0.110352 0.402263 0.453691 0.151 Uiso 0.569(7) 1 calc R U P A 1
C35 C 0.2036(6) 0.4820(3) 0.4275(3) 0.117(4) Uani 0.569(7) 1 d DG U P A 1
H35 H 0.166517 0.490422 0.374744 0.140 Uiso 0.569(7) 1 calc R U P A 1
C36 C 0.3361(5) 0.5754(2) 0.4049(3) 0.087(2) Uani 0.569(7) 1 d D U P A 1
H36A H 0.289307 0.578107 0.352730 0.131 Uiso 0.569(7) 1 calc R U P A 1
H36B H 0.328965 0.614847 0.436458 0.131 Uiso 0.569(7) 1 calc R U P A 1
H36C H 0.419412 0.568000 0.390721 0.131 Uiso 0.569(7) 1 calc R U P A 1
C41 C 0.2753(7) 0.5284(2) 0.4514(4) 0.082(3) Uani 0.431(7) 1 d DG U P A 2
C42 C 0.2621(8) 0.5416(3) 0.5369(4) 0.092(3) Uani 0.431(7) 1 d DG U P A 2
H42 H 0.284445 0.581553 0.558503 0.111 Uiso 0.431(7) 1 calc R U P A 2
N4 N 0.2160(8) 0.4962(4) 0.5909(3) 0.116(3) Uani 0.431(7) 1 d DG U P A 2
C43 C 0.1833(7) 0.4376(3) 0.5594(3) 0.101(3) Uani 0.431(7) 1 d DG U P A 2
H43 H 0.151817 0.406619 0.596303 0.121 Uiso 0.431(7) 1 calc R U P A 2
C44 C 0.1965(6) 0.4245(2) 0.4739(3) 0.0582(19) Uani 0.431(7) 1 d DG U P A 2
H44 H 0.174163 0.384495 0.452291 0.070 Uiso 0.431(7) 1 calc R U P A 2
C45 C 0.2426(6) 0.4699(3) 0.4198(3) 0.0499(15) Uani 0.431(7) 1 d DG U P A 2
H45 H 0.251650 0.460900 0.361383 0.060 Uiso 0.431(7) 1 calc R U P A 2
C46 C 0.3361(5) 0.5754(2) 0.4049(3) 0.128(4) Uani 0.431(7) 1 d D U P A 2
H46A H 0.341633 0.562527 0.345493 0.193 Uiso 0.431(7) 1 calc R U P A 2
H46B H 0.292753 0.615208 0.408728 0.193 Uiso 0.431(7) 1 calc R U P A 2
H46C H 0.415919 0.580820 0.428211 0.193 Uiso 0.431(7) 1 calc R U P A 2


_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
O11 C15 1.323(2) . ?
O11 C16 1.436(3) . ?
O12 C15 1.200(3) . ?
O13 C17 1.333(2) . ?
O13 C18 1.450(2) . ?
O14 C17 1.194(3) . ?
O21 C25 1.339(2) . ?
O21 C26 1.449(3) . ?
O22 C25 1.194(3) . ?
O23 C27 1.335(2) . ?
O23 C28 1.445(2) . ?
O24 C27 1.204(3) . ?
C11 C121 1.506(2) . ?
C11 C111 1.518(2) . ?
C11 C12 1.568(2) . ?
C11 H11 1.0000 . ?
C12 C15 1.512(3) . ?
C12 C13 1.536(2) . ?
C12 H12 1.0000 . ?
C13 C17 1.522(2) . ?
C13 C14 1.573(3) . ?
C13 H13 1.0000 . ?
C14 C112 1.512(3) . ?
C14 C122 1.513(2) . ?
C14 H14 1.0000 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C21 C211 1.517(2) . ?
C21 C221 1.521(3) . ?
C21 C22 1.564(2) . ?
C21 H21 1.0000 . ?
C22 C25 1.516(3) . ?
C22 C23 1.542(2) . ?
C22 H22 1.0000 . ?
C23 C27 1.521(3) . ?
C23 C24 1.565(3) . ?
C23 H23 1.0000 . ?
C24 C222 1.510(3) . ?
C24 C212 1.511(3) . ?
C24 H24 1.0000 . ?
C26 H26A 0.9800 . ?
C26 H26B 0.9800 . ?
C26 H26C 0.9800 . ?
C28 H28A 0.9800 . ?
C28 H28B 0.9800 . ?
C28 H28C 0.9800 . ?
C111 C116 1.389(3) . ?
C111 C112 1.396(3) . ?
C112 C113 1.379(3) . ?
C113 C114 1.392(3) . ?
C113 H113 0.9500 . ?
C114 C115 1.379(4) . ?
C114 H114 0.9500 . ?
C115 C116 1.389(3) . ?
C115 H115 0.9500 . ?
C116 H116 0.9500 . ?
C121 C126 1.386(3) . ?
C121 C122 1.397(3) . ?
C122 C123 1.388(3) . ?
C123 C124 1.401(3) . ?
C123 H123 0.9500 . ?
C124 C125 1.373(4) . ?
C124 H124 0.9500 . ?
C125 C126 1.396(3) . ?
C125 H125 0.9500 . ?
C126 H126 0.9500 . ?
C211 C216 1.378(3) . ?
C211 C212 1.401(3) . ?
C212 C213 1.389(3) . ?
C213 C214 1.392(3) . ?
C213 H213 0.9500 . ?
C214 C215 1.384(3) . ?
C214 H214 0.9500 . ?
C215 C216 1.402(3) . ?
C215 H215 0.9500 . ?
C216 H216 0.9500 . ?
C221 C226 1.385(3) . ?
C221 C222 1.404(3) . ?
C222 C223 1.388(3) . ?
C223 C224 1.394(3) . ?
C223 H223 0.9500 . ?
C224 C225 1.383(4) . ?
C224 H224 0.9500 . ?
C225 C226 1.393(3) . ?
C225 H225 0.9500 . ?
C226 H226 0.9500 . ?
C31 C32 1.3900 . ?
C31 C35 1.3900 . ?
C31 C36 1.498(6) . ?
C32 N3 1.3900 . ?
C32 H32 0.9500 . ?
N3 C33 1.3900 . ?
C33 C34 1.3900 . ?
C33 H33 0.9500 . ?
C34 C35 1.3900 . ?
C34 H34 0.9500 . ?
C35 H35 0.9500 . ?
C36 H36A 0.9800 . ?
C36 H36B 0.9800 . ?
C36 H36C 0.9800 . ?
C41 C42 1.3900 . ?
C41 C45 1.3900 . ?
C41 C46 1.418(6) . ?
C42 N4 1.3900 . ?
C42 H42 0.9500 . ?
N4 C43 1.3900 . ?
C43 C44 1.3900 . ?
C43 H43 0.9500 . ?
C44 C45 1.3900 . ?
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
C15 O11 C16 116.78(18) . . ?
C17 O13 C18 116.43(17) . . ?
C25 O21 C26 115.92(18) . . ?
C27 O23 C28 116.36(17) . . ?
C121 C11 C111 107.00(15) . . ?
C121 C11 C12 106.40(14) . . ?
C111 C11 C12 107.03(14) . . ?
C121 C11 H11 112.0 . . ?
C111 C11 H11 112.0 . . ?
C12 C11 H11 112.0 . . ?
C15 C12 C13 111.88(15) . . ?
C15 C12 C11 112.40(15) . . ?
C13 C12 C11 109.48(14) . . ?
C15 C12 H12 107.6 . . ?
C13 C12 H12 107.6 . . ?
C11 C12 H12 107.6 . . ?
C17 C13 C12 110.68(15) . . ?
C17 C13 C14 109.85(15) . . ?
C12 C13 C14 109.75(14) . . ?
C17 C13 H13 108.8 . . ?
C12 C13 H13 108.8 . . ?
C14 C13 H13 108.8 . . ?
C112 C14 C122 106.61(15) . . ?
C112 C14 C13 105.57(15) . . ?
C122 C14 C13 107.59(15) . . ?
C112 C14 H14 112.2 . . ?
C122 C14 H14 112.2 . . ?
C13 C14 H14 112.2 . . ?
O12 C15 O11 123.57(19) . . ?
O12 C15 C12 125.35(19) . . ?
O11 C15 C12 111.00(16) . . ?
O11 C16 H16A 109.5 . . ?
O11 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
O11 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
O14 C17 O13 123.16(18) . . ?
O14 C17 C13 125.68(19) . . ?
O13 C17 C13 111.16(16) . . ?
O13 C18 H18A 109.5 . . ?
O13 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
O13 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C211 C21 C221 106.72(15) . . ?
C211 C21 C22 106.17(14) . . ?
C221 C21 C22 106.77(14) . . ?
C211 C21 H21 112.3 . . ?
C221 C21 H21 112.3 . . ?
C22 C21 H21 112.3 . . ?
C25 C22 C23 111.66(14) . . ?
C25 C22 C21 112.11(15) . . ?
C23 C22 C21 109.17(15) . . ?
C25 C22 H22 107.9 . . ?
C23 C22 H22 107.9 . . ?
C21 C22 H22 107.9 . . ?
C27 C23 C22 110.65(15) . . ?
C27 C23 C24 110.57(16) . . ?
C22 C23 C24 110.34(14) . . ?
C27 C23 H23 108.4 . . ?
C22 C23 H23 108.4 . . ?
C24 C23 H23 108.4 . . ?
C222 C24 C212 107.17(15) . . ?
C222 C24 C23 105.19(15) . . ?
C212 C24 C23 107.68(15) . . ?
C222 C24 H24 112.1 . . ?
C212 C24 H24 112.1 . . ?
C23 C24 H24 112.1 . . ?
O22 C25 O21 123.31(19) . . ?
O22 C25 C22 125.47(19) . . ?
O21 C25 C22 111.19(16) . . ?
O21 C26 H26A 109.5 . . ?
O21 C26 H26B 109.5 . . ?
H26A C26 H26B 109.5 . . ?
O21 C26 H26C 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
O24 C27 O23 123.55(18) . . ?
O24 C27 C23 125.20(18) . . ?
O23 C27 C23 111.24(16) . . ?
O23 C28 H28A 109.5 . . ?
O23 C28 H28B 109.5 . . ?
H28A C28 H28B 109.5 . . ?
O23 C28 H28C 109.5 . . ?
H28A C28 H28C 109.5 . . ?
H28B C28 H28C 109.5 . . ?
C116 C111 C112 120.08(18) . . ?
C116 C111 C11 126.39(18) . . ?
C112 C111 C11 113.53(16) . . ?
C113 C112 C111 120.40(18) . . ?
C113 C112 C14 126.57(19) . . ?
C111 C112 C14 113.01(16) . . ?
C112 C113 C114 119.5(2) . . ?
C112 C113 H113 120.3 . . ?
C114 C113 H113 120.3 . . ?
C115 C114 C113 120.1(2) . . ?
C115 C114 H114 119.9 . . ?
C113 C114 H114 119.9 . . ?
C114 C115 C116 120.8(2) . . ?
C114 C115 H115 119.6 . . ?
C116 C115 H115 119.6 . . ?
C111 C116 C115 119.1(2) . . ?
C111 C116 H116 120.5 . . ?
C115 C116 H116 120.5 . . ?
C126 C121 C122 120.48(18) . . ?
C126 C121 C11 126.62(17) . . ?
C122 C121 C11 112.89(16) . . ?
C123 C122 C121 120.27(18) . . ?
C123 C122 C14 125.90(18) . . ?
C121 C122 C14 113.78(16) . . ?
C122 C123 C124 118.9(2) . . ?
C122 C123 H123 120.6 . . ?
C124 C123 H123 120.6 . . ?
C125 C124 C123 120.6(2) . . ?
C125 C124 H124 119.7 . . ?
C123 C124 H124 119.7 . . ?
C124 C125 C126 120.78(19) . . ?
C124 C125 H125 119.6 . . ?
C126 C125 H125 119.6 . . ?
C121 C126 C125 118.9(2) . . ?
C121 C126 H126 120.5 . . ?
C125 C126 H126 120.5 . . ?
C216 C211 C212 120.88(18) . . ?
C216 C211 C21 125.88(17) . . ?
C212 C211 C21 113.23(16) . . ?
C213 C212 C211 120.25(18) . . ?
C213 C212 C24 126.12(17) . . ?
C211 C212 C24 113.54(16) . . ?
C212 C213 C214 119.0(2) . . ?
C212 C213 H213 120.5 . . ?
C214 C213 H213 120.5 . . ?
C215 C214 C213 120.5(2) . . ?
C215 C214 H214 119.7 . . ?
C213 C214 H214 119.7 . . ?
C214 C215 C216 120.75(19) . . ?
C214 C215 H215 119.6 . . ?
C216 C215 H215 119.6 . . ?
C211 C216 C215 118.57(19) . . ?
C211 C216 H216 120.7 . . ?
C215 C216 H216 120.7 . . ?
C226 C221 C222 120.04(18) . . ?
C226 C221 C21 126.18(18) . . ?
C222 C221 C21 113.77(16) . . ?
C223 C222 C221 120.64(19) . . ?
C223 C222 C24 126.54(19) . . ?
C221 C222 C24 112.82(16) . . ?
C222 C223 C224 119.0(2) . . ?
C222 C223 H223 120.5 . . ?
C224 C223 H223 120.5 . . ?
C225 C224 C223 120.3(2) . . ?
C225 C224 H224 119.9 . . ?
C223 C224 H224 119.9 . . ?
C224 C225 C226 121.1(2) . . ?
C224 C225 H225 119.5 . . ?
C226 C225 H225 119.5 . . ?
C221 C226 C225 119.0(2) . . ?
C221 C226 H226 120.5 . . ?
C225 C226 H226 120.5 . . ?
C32 C31 C35 120.0 . . ?
C32 C31 C36 119.0(4) . . ?
C35 C31 C36 120.8(4) . . ?
C31 C32 N3 120.0 . . ?
C31 C32 H32 120.0 . . ?
N3 C32 H32 120.0 . . ?
C33 N3 C32 120.0 . . ?
N3 C33 C34 120.0 . . ?
N3 C33 H33 120.0 . . ?
C34 C33 H33 120.0 . . ?
C33 C34 C35 120.0 . . ?
C33 C34 H34 120.0 . . ?
C35 C34 H34 120.0 . . ?
C34 C35 C31 120.0 . . ?
C34 C35 H35 120.0 . . ?
C31 C35 H35 120.0 . . ?
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 . . ?
C42 C41 C45 120.0 . . ?
C42 C41 C46 114.7(4) . . ?
C45 C41 C46 124.9(4) . . ?
N4 C42 C41 120.0 . . ?
N4 C42 H42 120.0 . . ?
C41 C42 H42 120.0 . . ?
C43 N4 C42 120.0 . . ?
N4 C43 C44 120.0 . . ?
N4 C43 H43 120.0 . . ?
C44 C43 H43 120.0 . . ?
C43 C44 C45 120.0 . . ?
C43 C44 H44 120.0 . . ?
C45 C44 H44 120.0 . . ?
C44 C45 C41 120.0 . . ?
C44 C45 H45 120.0 . . ?
C41 C45 H45 120.0 . . ?
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
C121 C11 C12 C15 64.69(19) . . . . ?
C111 C11 C12 C15 178.82(15) . . . . ?
C121 C11 C12 C13 -60.29(18) . . . . ?
C111 C11 C12 C13 53.84(18) . . . . ?
C15 C12 C13 C17 117.73(17) . . . . ?
C11 C12 C13 C17 -116.99(16) . . . . ?
C15 C12 C13 C14 -120.86(17) . . . . ?
C11 C12 C13 C14 4.42(19) . . . . ?
C17 C13 C14 C112 61.39(18) . . . . ?
C12 C13 C14 C112 -60.52(18) . . . . ?
C17 C13 C14 C122 174.94(15) . . . . ?
C12 C13 C14 C122 53.03(19) . . . . ?
C16 O11 C15 O12 -0.8(4) . . . . ?
C16 O11 C15 C12 176.1(2) . . . . ?
C13 C12 C15 O12 -14.7(3) . . . . ?
C11 C12 C15 O12 -138.4(2) . . . . ?
C13 C12 C15 O11 168.41(17) . . . . ?
C11 C12 C15 O11 44.7(2) . . . . ?
C18 O13 C17 O14 3.3(3) . . . . ?
C18 O13 C17 C13 -177.49(17) . . . . ?
C12 C13 C17 O14 -4.9(3) . . . . ?
C14 C13 C17 O14 -126.3(2) . . . . ?
C12 C13 C17 O13 175.87(15) . . . . ?
C14 C13 C17 O13 54.5(2) . . . . ?
C211 C21 C22 C25 64.37(19) . . . . ?
C221 C21 C22 C25 177.96(15) . . . . ?
C211 C21 C22 C23 -59.89(18) . . . . ?
C221 C21 C22 C23 53.70(18) . . . . ?
C25 C22 C23 C27 117.28(17) . . . . ?
C21 C22 C23 C27 -118.19(16) . . . . ?
C25 C22 C23 C24 -120.03(17) . . . . ?
C21 C22 C23 C24 4.50(19) . . . . ?
C27 C23 C24 C222 61.87(18) . . . . ?
C22 C23 C24 C222 -60.86(18) . . . . ?
C27 C23 C24 C212 175.93(14) . . . . ?
C22 C23 C24 C212 53.19(19) . . . . ?
C26 O21 C25 O22 -1.2(3) . . . . ?
C26 O21 C25 C22 176.81(19) . . . . ?
C23 C22 C25 O22 -11.6(3) . . . . ?
C21 C22 C25 O22 -134.5(2) . . . . ?
C23 C22 C25 O21 170.40(16) . . . . ?
C21 C22 C25 O21 47.5(2) . . . . ?
C28 O23 C27 O24 2.6(3) . . . . ?
C28 O23 C27 C23 -178.20(17) . . . . ?
C22 C23 C27 O24 -6.5(3) . . . . ?
C24 C23 C27 O24 -129.1(2) . . . . ?
C22 C23 C27 O23 174.32(15) . . . . ?
C24 C23 C27 O23 51.8(2) . . . . ?
C121 C11 C111 C116 -125.6(2) . . . . ?
C12 C11 C111 C116 120.6(2) . . . . ?
C121 C11 C111 C112 53.97(19) . . . . ?
C12 C11 C111 C112 -59.76(19) . . . . ?
C116 C111 C112 C113 -0.6(3) . . . . ?
C11 C111 C112 C113 179.76(17) . . . . ?
C116 C111 C112 C14 -179.11(17) . . . . ?
C11 C111 C112 C14 1.3(2) . . . . ?
C122 C14 C112 C113 126.5(2) . . . . ?
C13 C14 C112 C113 -119.2(2) . . . . ?
C122 C14 C112 C111 -55.1(2) . . . . ?
C13 C14 C112 C111 59.16(19) . . . . ?
C111 C112 C113 C114 1.9(3) . . . . ?
C14 C112 C113 C114 -179.85(19) . . . . ?
C112 C113 C114 C115 -1.7(3) . . . . ?
C113 C114 C115 C116 0.3(3) . . . . ?
C112 C111 C116 C115 -0.8(3) . . . . ?
C11 C111 C116 C115 178.79(18) . . . . ?
C114 C115 C116 C111 0.9(3) . . . . ?
C111 C11 C121 C126 125.2(2) . . . . ?
C12 C11 C121 C126 -120.7(2) . . . . ?
C111 C11 C121 C122 -54.7(2) . . . . ?
C12 C11 C121 C122 59.43(19) . . . . ?
C126 C121 C122 C123 -1.8(3) . . . . ?
C11 C121 C122 C123 178.14(18) . . . . ?
C126 C121 C122 C14 -179.25(18) . . . . ?
C11 C121 C122 C14 0.7(2) . . . . ?
C112 C14 C122 C123 -122.9(2) . . . . ?
C13 C14 C122 C123 124.2(2) . . . . ?
C112 C14 C122 C121 54.4(2) . . . . ?
C13 C14 C122 C121 -58.5(2) . . . . ?
C121 C122 C123 C124 0.2(3) . . . . ?
C14 C122 C123 C124 177.4(2) . . . . ?
C122 C123 C124 C125 1.2(4) . . . . ?
C123 C124 C125 C126 -1.0(4) . . . . ?
C122 C121 C126 C125 1.9(3) . . . . ?
C11 C121 C126 C125 -178.00(19) . . . . ?
C124 C125 C126 C121 -0.5(3) . . . . ?
C221 C21 C211 C216 125.2(2) . . . . ?
C22 C21 C211 C216 -121.2(2) . . . . ?
C221 C21 C211 C212 -54.2(2) . . . . ?
C22 C21 C211 C212 59.42(19) . . . . ?
C216 C211 C212 C213 -2.0(3) . . . . ?
C21 C211 C212 C213 177.41(18) . . . . ?
C216 C211 C212 C24 -178.89(17) . . . . ?
C21 C211 C212 C24 0.5(2) . . . . ?
C222 C24 C212 C213 -122.1(2) . . . . ?
C23 C24 C212 C213 125.2(2) . . . . ?
C222 C24 C212 C211 54.6(2) . . . . ?
C23 C24 C212 C211 -58.2(2) . . . . ?
C211 C212 C213 C214 0.2(3) . . . . ?
C24 C212 C213 C214 176.6(2) . . . . ?
C212 C213 C214 C215 1.4(3) . . . . ?
C213 C214 C215 C216 -1.2(4) . . . . ?
C212 C211 C216 C215 2.2(3) . . . . ?
C21 C211 C216 C215 -177.15(19) . . . . ?
C214 C215 C216 C211 -0.6(3) . . . . ?
C211 C21 C221 C226 -126.0(2) . . . . ?
C22 C21 C221 C226 120.8(2) . . . . ?
C211 C21 C221 C222 53.6(2) . . . . ?
C22 C21 C221 C222 -59.7(2) . . . . ?
C226 C221 C222 C223 0.1(3) . . . . ?
C21 C221 C222 C223 -179.47(17) . . . . ?
C226 C221 C222 C24 -179.47(18) . . . . ?
C21 C221 C222 C24 0.9(2) . . . . ?
C212 C24 C222 C223 125.3(2) . . . . ?
C23 C24 C222 C223 -120.2(2) . . . . ?
C212 C24 C222 C221 -55.1(2) . . . . ?
C23 C24 C222 C221 59.31(19) . . . . ?
C221 C222 C223 C224 0.5(3) . . . . ?
C24 C222 C223 C224 -180.0(2) . . . . ?
C222 C223 C224 C225 -0.6(4) . . . . ?
C223 C224 C225 C226 0.1(4) . . . . ?
C222 C221 C226 C225 -0.6(3) . . . . ?
C21 C221 C226 C225 178.9(2) . . . . ?
C224 C225 C226 C221 0.5(4) . . . . ?
C35 C31 C32 N3 0.0 . . . . ?
C36 C31 C32 N3 -174.5(5) . . . . ?
C31 C32 N3 C33 0.0 . . . . ?
C32 N3 C33 C34 0.0 . . . . ?
N3 C33 C34 C35 0.0 . . . . ?
C33 C34 C35 C31 0.0 . . . . ?
C32 C31 C35 C34 0.0 . . . . ?
C36 C31 C35 C34 174.4(5) . . . . ?
C45 C41 C42 N4 0.0 . . . . ?
C46 C41 C42 N4 -172.8(7) . . . . ?
C41 C42 N4 C43 0.0 . . . . ?
C42 N4 C43 C44 0.0 . . . . ?
N4 C43 C44 C45 0.0 . . . . ?
C43 C44 C45 C41 0.0 . . . . ?
C42 C41 C45 C44 0.0 . . . . ?
C46 C41 C45 C44 172.0(7) . . . . ?

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
C12 H12 O14 1.00 2.26 2.803(2) 113 . yes
C13 H13 O12 1.00 2.33 2.831(3) 110 . yes
C22 H22 O24 1.00 2.26 2.800(2) 113 . yes
C23 H23 O22 1.00 2.32 2.826(3) 111 . yes
C23 H23 O11 1.00 2.52 3.398(2) 146 4_665 yes
C33 H33 O12 0.95 2.34 3.158(4) 144 . yes
C114 H114 N4 0.95 2.56 3.26(4) 131 4_565 yes
C116 H116 O24 0.95 2.56 3.394(3) 147 4_466 yes
C224 H224 N3 0.95 2.61 3.41(2) 143 3_666 yes
C226 H226 O14 0.95 2.54 3.379(3) 147 4_565 yes

_refine_diff_density_max         0.473
_refine_diff_density_min         -0.467
_refine_diff_density_rms         0.057


_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_ja116
_database_code_depnum_ccdc_archive 'CCDC 2236048'
loop_
_audit_author_name
_audit_author_address
'Eric Hosten'
;Nelson Mandela University
South Africa
;
_audit_update_record             
;
2023-01-13 deposited with the CCDC.	2023-02-28 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        
trans-α,α,α',α'-tetraphenyl-9,10-dihydro-9,10-ethanoanthracene-11,12-dimethanol
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C42 H34 O2, C6 H7 N'
_chemical_formula_sum            'C48 H41 N O2'
_chemical_formula_weight         663.82

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                   18.950(4)
_cell_length_b                   8.983(2)
_cell_length_c                   22.253(5)
_cell_angle_alpha                90
_cell_angle_beta                 107.012(9)
_cell_angle_gamma                90
_cell_volume                     3622.2(15)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    9801
_cell_measurement_theta_min      2.49
_cell_measurement_theta_max      28.41

_exptl_crystal_description       parallelepiped
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.217
_exptl_crystal_F_000             1408
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.989
_exptl_crystal_size_mid          0.469
_exptl_crystal_size_min          0.409
_exptl_absorpt_coefficient_mu    0.073
_shelx_estimated_absorpt_T_min   0.931
_shelx_estimated_absorpt_T_max   0.971
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_correction_T_min  0.9318
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_process_details   'SADABS-2008/1 (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            48986
_diffrn_reflns_av_unetI/netI     0.0237
_diffrn_reflns_av_R_equivalents  0.0310
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_theta_min         1.914
_diffrn_reflns_theta_max         28.660
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.972
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.972
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.972
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             9067
_reflns_number_gt                6901
_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).

A reflection with large difference between its observed and calculated
intensities was omitted. This is due to obstruction by the beam stop.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0526P)²+1.0846P] 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       0.0027(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         9067
_refine_ls_number_parameters     464
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0651
_refine_ls_R_factor_gt           0.0463
_refine_ls_wR_factor_ref         0.1321
_refine_ls_wR_factor_gt          0.1159
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_restrained_S_all      1.035
_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
O11 O 0.35105(5) 1.05045(12) 0.22977(5) 0.0490(2) Uani 1 1 d . . . . .
H11 H 0.354369 1.031266 0.194673 0.074 Uiso 1 1 calc R U . . .
O16 O 0.31221(5) 0.95713(11) 0.11281(4) 0.0417(2) Uani 1 1 d . . . . .
H16 H 0.330172 0.948890 0.083623 0.062 Uiso 1 1 calc R U . . .
N1 N 0.40663(7) 0.85882(15) 0.04962(6) 0.0539(3) Uani 1 1 d . . . . .
C2 C 0.41566(10) 0.8623(2) -0.00742(9) 0.0639(5) Uani 1 1 d . . . . .
C3 C 0.47175(14) 0.7844(3) -0.02137(14) 0.0944(8) Uani 1 1 d . . . . .
H3 H 0.477140 0.787811 -0.061562 0.113 Uiso 1 1 calc R U . . .
C4 C 0.51833(15) 0.7038(3) 0.02395(17) 0.1111(10) Uani 1 1 d . . . . .
H4 H 0.556153 0.650701 0.014955 0.133 Uiso 1 1 calc R U . . .
C5 C 0.51075(11) 0.6985(3) 0.08405(14) 0.0936(7) Uani 1 1 d . . . . .
H5 H 0.543089 0.643726 0.115845 0.112 Uiso 1 1 calc R U . . .
C6 C 0.45390(10) 0.7771(2) 0.09461(10) 0.0672(5) Uani 1 1 d . . . . .
H6 H 0.447492 0.774214 0.134460 0.081 Uiso 1 1 calc R U . . .
C7 C 0.36293(15) 0.9548(3) -0.05454(10) 0.0900(7) Uani 1 1 d . . . . .
H7A H 0.377766 0.959172 -0.092219 0.135 Uiso 1 1 calc R U . . .
H7B H 0.362191 1.053544 -0.038214 0.135 Uiso 1 1 calc R U . . .
H7C H 0.314523 0.911948 -0.063846 0.135 Uiso 1 1 calc R U . . .
C11 C 0.31003(6) 0.93659(15) 0.24879(6) 0.0367(3) Uani 1 1 d . . . . .
C12 C 0.23690(6) 0.90257(13) 0.19464(5) 0.0322(2) Uani 1 1 d . . . . .
H12 H 0.248670 0.821045 0.169917 0.039 Uiso 1 1 calc R U . . .
C13 C 0.17068(6) 0.84627(14) 0.21812(6) 0.0357(3) Uani 1 1 d . . . . .
H13 H 0.187122 0.775616 0.252986 0.043 Uiso 1 1 calc R U . . .
C14 C 0.20898(6) 1.03253(13) 0.14834(5) 0.0322(2) Uani 1 1 d . . . . .
H14 H 0.222256 1.123579 0.173370 0.039 Uiso 1 1 calc R U . . .
C15 C 0.12245(6) 1.02819(14) 0.12612(6) 0.0368(3) Uani 1 1 d . . . . .
H15 H 0.101776 1.097153 0.091285 0.044 Uiso 1 1 calc R U . . .
C16 C 0.24738(6) 1.04632(13) 0.09351(6) 0.0336(2) Uani 1 1 d . . . . .
C21 C 0.35789(7) 0.79675(17) 0.26279(6) 0.0447(3) Uani 1 1 d . . . . .
C22 C 0.33046(10) 0.65502(19) 0.25287(8) 0.0594(4) Uani 1 1 d . . . . .
H22 H 0.279700 0.640541 0.238237 0.071 Uiso 1 1 calc R U . . .
C23 C 0.37701(13) 0.5329(2) 0.26426(10) 0.0806(6) Uani 1 1 d . . . . .
H23 H 0.357535 0.437169 0.257814 0.097 Uiso 1 1 calc R U . . .
C24 C 0.45181(14) 0.5534(3) 0.28504(11) 0.0937(8) Uani 1 1 d . . . . .
H24 H 0.483255 0.471609 0.292251 0.112 Uiso 1 1 calc R U . . .
C25 C 0.48006(11) 0.6927(3) 0.29512(11) 0.0925(7) Uani 1 1 d . . . . .
H25 H 0.530916 0.706411 0.308870 0.111 Uiso 1 1 calc R U . . .
C26 C 0.43397(9) 0.8134(2) 0.28511(8) 0.0663(5) Uani 1 1 d . . . . .
H26 H 0.453994 0.908410 0.293423 0.080 Uiso 1 1 calc R U . . .
C31 C 0.29636(7) 0.99826(16) 0.30847(6) 0.0404(3) Uani 1 1 d . . . . .
C32 C 0.30121(8) 0.91204(19) 0.36099(7) 0.0520(4) Uani 1 1 d . . . . .
H32 H 0.312415 0.811403 0.360163 0.062 Uiso 1 1 calc R U . . .
C33 C 0.28975(10) 0.9719(2) 0.41508(8) 0.0671(5) Uani 1 1 d . . . . .
H33 H 0.294100 0.911826 0.450022 0.081 Uiso 1 1 calc R U . . .
C34 C 0.27224(11) 1.1180(3) 0.41673(9) 0.0742(5) Uani 1 1 d . . . . .
H34 H 0.263916 1.158401 0.452531 0.089 Uiso 1 1 calc R U . . .
C35 C 0.26694(10) 1.2053(2) 0.36515(10) 0.0704(5) Uani 1 1 d . . . . .
H35 H 0.254493 1.305280 0.366033 0.084 Uiso 1 1 calc R U . . .
C36 C 0.27988(8) 1.14690(18) 0.31154(8) 0.0536(4) Uani 1 1 d . . . . .
H36 H 0.277393 1.208658 0.277439 0.064 Uiso 1 1 calc R U . . .
C41 C 0.12870(6) 0.97407(15) 0.23457(6) 0.0384(3) Uani 1 1 d . . . . .
C42 C 0.10161(7) 1.07159(15) 0.18476(7) 0.0402(3) Uani 1 1 d . . . . .
C43 C 0.06210(8) 1.19508(18) 0.19246(8) 0.0538(4) Uani 1 1 d . . . . .
H43 H 0.044775 1.262283 0.159659 0.065 Uiso 1 1 calc R U . . .
C44 C 0.04831(9) 1.2184(2) 0.25006(10) 0.0675(5) Uani 1 1 d . . . . .
H44 H 0.021576 1.301579 0.255426 0.081 Uiso 1 1 calc R U . . .
C45 C 0.07361(9) 1.1205(2) 0.29864(9) 0.0636(5) Uani 1 1 d . . . . .
H45 H 0.063649 1.136844 0.336616 0.076 Uiso 1 1 calc R U . . .
C46 C 0.11385(8) 0.99756(18) 0.29140(7) 0.0499(3) Uani 1 1 d . . . . .
H46 H 0.130972 0.930685 0.324362 0.060 Uiso 1 1 calc R U . . .
C51 C 0.09464(6) 0.87227(15) 0.11031(6) 0.0383(3) Uani 1 1 d . . . . .
C52 C 0.11903(6) 0.77422(14) 0.16059(6) 0.0377(3) Uani 1 1 d . . . . .
C53 C 0.09583(8) 0.62907(16) 0.15477(7) 0.0480(3) Uani 1 1 d . . . . .
H53 H 0.112323 0.562909 0.188080 0.058 Uiso 1 1 calc R U . . .
C54 C 0.04721(9) 0.58250(19) 0.09816(8) 0.0591(4) Uani 1 1 d . . . . .
H54 H 0.030905 0.484332 0.093810 0.071 Uiso 1 1 calc R U . . .
C55 C 0.02293(9) 0.6787(2) 0.04871(8) 0.0599(4) Uani 1 1 d . . . . .
H55 H -0.009832 0.645535 0.011297 0.072 Uiso 1 1 calc R U . . .
C56 C 0.04671(8) 0.82412(18) 0.05402(7) 0.0497(3) Uani 1 1 d . . . . .
H56 H 0.030787 0.889192 0.020241 0.060 Uiso 1 1 calc R U . . .
C61 C 0.20062(7) 0.98992(15) 0.02900(6) 0.0390(3) Uani 1 1 d . . . . .
C62 C 0.20068(9) 0.84042(18) 0.01586(8) 0.0557(4) Uani 1 1 d . . . . .
H62 H 0.227368 0.775262 0.046642 0.067 Uiso 1 1 calc R U . . .
C63 C 0.16169(11) 0.7855(2) -0.04240(10) 0.0738(5) Uani 1 1 d . . . . .
H63 H 0.162355 0.683802 -0.050138 0.089 Uiso 1 1 calc R U . . .
C64 C 0.12218(11) 0.8781(3) -0.08881(9) 0.0778(6) Uani 1 1 d . . . . .
H64 H 0.096892 0.840647 -0.128184 0.093 Uiso 1 1 calc R U . . .
C65 C 0.12049(10) 1.0257(3) -0.07644(8) 0.0732(5) Uani 1 1 d . . . . .
H65 H 0.092949 1.089699 -0.107316 0.088 Uiso 1 1 calc R U . . .
C66 C 0.15951(8) 1.08217(19) -0.01809(7) 0.0526(4) Uani 1 1 d . . . . .
H66 H 0.157977 1.183769 -0.010536 0.063 Uiso 1 1 calc R U . . .
C71 C 0.26958(7) 1.20821(14) 0.09015(6) 0.0360(3) Uani 1 1 d . . . . .
C72 C 0.22224(8) 1.32326(16) 0.09352(8) 0.0494(3) Uani 1 1 d . . . . .
H72 H 0.175445 1.301260 0.096549 0.059 Uiso 1 1 calc R U . . .
C73 C 0.24320(10) 1.46877(17) 0.09249(9) 0.0582(4) Uani 1 1 d . . . . .
H73 H 0.210296 1.544545 0.093944 0.070 Uiso 1 1 calc R U . . .
C74 C 0.31255(10) 1.50339(18) 0.08930(8) 0.0578(4) Uani 1 1 d . . . . .
H74 H 0.327117 1.602322 0.089594 0.069 Uiso 1 1 calc R U . . .
C75 C 0.35985(9) 1.39217(18) 0.08572(8) 0.0553(4) Uani 1 1 d . . . . .
H75 H 0.406822 1.415246 0.083379 0.066 Uiso 1 1 calc R U . . .
C76 C 0.33854(7) 1.24550(16) 0.08553(7) 0.0442(3) Uani 1 1 d . . . . .
H76 H 0.371042 1.170495 0.082253 0.053 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
O11 C11 1.4219(15) . ?
O11 H11 0.8200 . ?
O16 C16 1.4237(14) . ?
O16 H16 0.8200 . ?
N1 C2 1.330(2) . ?
N1 C6 1.348(2) . ?
C2 C3 1.382(3) . ?
C2 C7 1.475(3) . ?
C3 C4 1.342(4) . ?
C3 H3 0.9300 . ?
C4 C5 1.387(4) . ?
C4 H4 0.9300 . ?
C5 C6 1.365(3) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
C11 C21 1.5272(19) . ?
C11 C31 1.5294(18) . ?
C11 C12 1.5776(17) . ?
C12 C14 1.5445(16) . ?
C12 C13 1.5771(16) . ?
C12 H12 0.9800 . ?
C13 C41 1.5017(18) . ?
C13 C52 1.5109(18) . ?
C13 H13 0.9800 . ?
C14 C15 1.5686(16) . ?
C14 C16 1.5979(16) . ?
C14 H14 0.9800 . ?
C15 C51 1.5015(18) . ?
C15 C42 1.5206(18) . ?
C15 H15 0.9800 . ?
C16 C71 1.5218(17) . ?
C16 C61 1.5356(18) . ?
C21 C22 1.368(2) . ?
C21 C26 1.389(2) . ?
C22 C23 1.384(2) . ?
C22 H22 0.9300 . ?
C23 C24 1.369(3) . ?
C23 H23 0.9300 . ?
C24 C25 1.353(4) . ?
C24 H24 0.9300 . ?
C25 C26 1.369(3) . ?
C25 H25 0.9300 . ?
C26 H26 0.9300 . ?
C31 C36 1.377(2) . ?
C31 C32 1.383(2) . ?
C32 C33 1.392(2) . ?
C32 H32 0.9300 . ?
C33 C34 1.357(3) . ?
C33 H33 0.9300 . ?
C34 C35 1.370(3) . ?
C34 H34 0.9300 . ?
C35 C36 1.389(2) . ?
C35 H35 0.9300 . ?
C36 H36 0.9300 . ?
C41 C42 1.3880(19) . ?
C41 C46 1.3898(19) . ?
C42 C43 1.3768(19) . ?
C43 C44 1.397(2) . ?
C43 H43 0.9300 . ?
C44 C45 1.367(3) . ?
C44 H44 0.9300 . ?
C45 C46 1.378(2) . ?
C45 H45 0.9300 . ?
C46 H46 0.9300 . ?
C51 C56 1.3840(19) . ?
C51 C52 1.3924(19) . ?
C52 C53 1.3699(19) . ?
C53 C54 1.390(2) . ?
C53 H53 0.9300 . ?
C54 C55 1.369(3) . ?
C54 H54 0.9300 . ?
C55 C56 1.376(2) . ?
C55 H55 0.9300 . ?
C56 H56 0.9300 . ?
C61 C62 1.374(2) . ?
C61 C66 1.3836(19) . ?
C62 C63 1.382(2) . ?
C62 H62 0.9300 . ?
C63 C64 1.367(3) . ?
C63 H63 0.9300 . ?
C64 C65 1.356(3) . ?
C64 H64 0.9300 . ?
C65 C66 1.388(2) . ?
C65 H65 0.9300 . ?
C66 H66 0.9300 . ?
C71 C76 1.3815(18) . ?
C71 C72 1.3849(18) . ?
C72 C73 1.368(2) . ?
C72 H72 0.9300 . ?
C73 C74 1.372(2) . ?
C73 H73 0.9300 . ?
C74 C75 1.360(2) . ?
C74 H74 0.9300 . ?
C75 C76 1.378(2) . ?
C75 H75 0.9300 . ?
C76 H76 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
C11 O11 H11 109.5 . . ?
C16 O16 H16 109.5 . . ?
C2 N1 C6 118.59(15) . . ?
N1 C2 C3 121.6(2) . . ?
N1 C2 C7 116.25(17) . . ?
C3 C2 C7 122.1(2) . . ?
C4 C3 C2 119.0(2) . . ?
C4 C3 H3 120.5 . . ?
C2 C3 H3 120.5 . . ?
C3 C4 C5 120.8(2) . . ?
C3 C4 H4 119.6 . . ?
C5 C4 H4 119.6 . . ?
C6 C5 C4 117.3(2) . . ?
C6 C5 H5 121.4 . . ?
C4 C5 H5 121.4 . . ?
N1 C6 C5 122.7(2) . . ?
N1 C6 H6 118.7 . . ?
C5 C6 H6 118.7 . . ?
C2 C7 H7A 109.5 . . ?
C2 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C2 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
O11 C11 C21 107.97(10) . . ?
O11 C11 C31 104.14(11) . . ?
C21 C11 C31 111.24(10) . . ?
O11 C11 C12 110.27(10) . . ?
C21 C11 C12 109.45(11) . . ?
C31 C11 C12 113.54(10) . . ?
C14 C12 C13 108.24(9) . . ?
C14 C12 C11 114.58(10) . . ?
C13 C12 C11 114.53(10) . . ?
C14 C12 H12 106.3 . . ?
C13 C12 H12 106.3 . . ?
C11 C12 H12 106.3 . . ?
C41 C13 C52 106.02(10) . . ?
C41 C13 C12 111.42(10) . . ?
C52 C13 C12 103.74(10) . . ?
C41 C13 H13 111.7 . . ?
C52 C13 H13 111.7 . . ?
C12 C13 H13 111.7 . . ?
C12 C14 C15 108.30(9) . . ?
C12 C14 C16 115.11(9) . . ?
C15 C14 C16 115.39(10) . . ?
C12 C14 H14 105.7 . . ?
C15 C14 H14 105.7 . . ?
C16 C14 H14 105.7 . . ?
C51 C15 C42 106.19(10) . . ?
C51 C15 C14 111.10(10) . . ?
C42 C15 C14 103.47(10) . . ?
C51 C15 H15 111.9 . . ?
C42 C15 H15 111.9 . . ?
C14 C15 H15 111.9 . . ?
O16 C16 C71 109.02(10) . . ?
O16 C16 C61 107.90(10) . . ?
C71 C16 C61 111.20(10) . . ?
O16 C16 C14 105.76(9) . . ?
C71 C16 C14 107.81(9) . . ?
C61 C16 C14 114.91(10) . . ?
C22 C21 C26 117.63(15) . . ?
C22 C21 C11 123.88(13) . . ?
C26 C21 C11 118.46(15) . . ?
C21 C22 C23 121.09(18) . . ?
C21 C22 H22 119.5 . . ?
C23 C22 H22 119.5 . . ?
C24 C23 C22 119.8(2) . . ?
C24 C23 H23 120.1 . . ?
C22 C23 H23 120.1 . . ?
C25 C24 C23 120.06(19) . . ?
C25 C24 H24 120.0 . . ?
C23 C24 H24 120.0 . . ?
C24 C25 C26 120.2(2) . . ?
C24 C25 H25 119.9 . . ?
C26 C25 H25 119.9 . . ?
C25 C26 C21 121.2(2) . . ?
C25 C26 H26 119.4 . . ?
C21 C26 H26 119.4 . . ?
C36 C31 C32 117.46(14) . . ?
C36 C31 C11 119.51(13) . . ?
C32 C31 C11 123.02(13) . . ?
C31 C32 C33 121.73(16) . . ?
C31 C32 H32 119.1 . . ?
C33 C32 H32 119.1 . . ?
C34 C33 C32 119.88(18) . . ?
C34 C33 H33 120.1 . . ?
C32 C33 H33 120.1 . . ?
C33 C34 C35 119.34(17) . . ?
C33 C34 H34 120.3 . . ?
C35 C34 H34 120.3 . . ?
C34 C35 C36 121.01(18) . . ?
C34 C35 H35 119.5 . . ?
C36 C35 H35 119.5 . . ?
C31 C36 C35 120.55(17) . . ?
C31 C36 H36 119.7 . . ?
C35 C36 H36 119.7 . . ?
C42 C41 C46 120.32(13) . . ?
C42 C41 C13 112.73(11) . . ?
C46 C41 C13 126.91(13) . . ?
C43 C42 C41 119.77(13) . . ?
C43 C42 C15 126.92(13) . . ?
C41 C42 C15 113.28(11) . . ?
C42 C43 C44 119.31(16) . . ?
C42 C43 H43 120.3 . . ?
C44 C43 H43 120.3 . . ?
C45 C44 C43 120.85(15) . . ?
C45 C44 H44 119.6 . . ?
C43 C44 H44 119.6 . . ?
C44 C45 C46 120.08(15) . . ?
C44 C45 H45 120.0 . . ?
C46 C45 H45 120.0 . . ?
C45 C46 C41 119.63(16) . . ?
C45 C46 H46 120.2 . . ?
C41 C46 H46 120.2 . . ?
C56 C51 C52 120.35(13) . . ?
C56 C51 C15 126.58(13) . . ?
C52 C51 C15 112.99(11) . . ?
C53 C52 C51 120.28(13) . . ?
C53 C52 C13 126.74(13) . . ?
C51 C52 C13 112.98(11) . . ?
C52 C53 C54 118.78(15) . . ?
C52 C53 H53 120.6 . . ?
C54 C53 H53 120.6 . . ?
C55 C54 C53 121.10(15) . . ?
C55 C54 H54 119.5 . . ?
C53 C54 H54 119.5 . . ?
C54 C55 C56 120.40(15) . . ?
C54 C55 H55 119.8 . . ?
C56 C55 H55 119.8 . . ?
C55 C56 C51 119.09(15) . . ?
C55 C56 H56 120.5 . . ?
C51 C56 H56 120.5 . . ?
C62 C61 C66 117.34(14) . . ?
C62 C61 C16 119.02(12) . . ?
C66 C61 C16 123.61(12) . . ?
C61 C62 C63 121.01(17) . . ?
C61 C62 H62 119.5 . . ?
C63 C62 H62 119.5 . . ?
C64 C63 C62 121.04(18) . . ?
C64 C63 H63 119.5 . . ?
C62 C63 H63 119.5 . . ?
C65 C64 C63 118.83(17) . . ?
C65 C64 H64 120.6 . . ?
C63 C64 H64 120.6 . . ?
C64 C65 C66 120.60(18) . . ?
C64 C65 H65 119.7 . . ?
C66 C65 H65 119.7 . . ?
C61 C66 C65 121.16(16) . . ?
C61 C66 H66 119.4 . . ?
C65 C66 H66 119.4 . . ?
C76 C71 C72 117.70(12) . . ?
C76 C71 C16 121.09(11) . . ?
C72 C71 C16 121.17(11) . . ?
C73 C72 C71 121.07(13) . . ?
C73 C72 H72 119.5 . . ?
C71 C72 H72 119.5 . . ?
C72 C73 C74 120.29(15) . . ?
C72 C73 H73 119.9 . . ?
C74 C73 H73 119.9 . . ?
C75 C74 C73 119.61(14) . . ?
C75 C74 H74 120.2 . . ?
C73 C74 H74 120.2 . . ?
C74 C75 C76 120.33(14) . . ?
C74 C75 H75 119.8 . . ?
C76 C75 H75 119.8 . . ?
C75 C76 C71 120.96(13) . . ?
C75 C76 H76 119.5 . . ?
C71 C76 H76 119.5 . . ?

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
C6 N1 C2 C3 0.2(3) . . . . ?
C6 N1 C2 C7 -179.30(17) . . . . ?
N1 C2 C3 C4 -0.3(3) . . . . ?
C7 C2 C3 C4 179.2(2) . . . . ?
C2 C3 C4 C5 -0.2(4) . . . . ?
C3 C4 C5 C6 0.7(4) . . . . ?
C2 N1 C6 C5 0.3(3) . . . . ?
C4 C5 C6 N1 -0.7(3) . . . . ?
O11 C11 C12 C14 -24.54(14) . . . . ?
C21 C11 C12 C14 -143.17(10) . . . . ?
C31 C11 C12 C14 91.88(12) . . . . ?
O11 C11 C12 C13 -150.49(10) . . . . ?
C21 C11 C12 C13 90.87(12) . . . . ?
C31 C11 C12 C13 -34.08(15) . . . . ?
C14 C12 C13 C41 -44.36(13) . . . . ?
C11 C12 C13 C41 84.83(13) . . . . ?
C14 C12 C13 C52 69.28(12) . . . . ?
C11 C12 C13 C52 -161.53(10) . . . . ?
C13 C12 C14 C15 -17.18(13) . . . . ?
C11 C12 C14 C15 -146.34(10) . . . . ?
C13 C12 C14 C16 -148.00(10) . . . . ?
C11 C12 C14 C16 82.84(13) . . . . ?
C12 C14 C15 C51 -44.34(13) . . . . ?
C16 C14 C15 C51 86.33(13) . . . . ?
C12 C14 C15 C42 69.22(12) . . . . ?
C16 C14 C15 C42 -160.11(10) . . . . ?
C12 C14 C16 O16 -15.74(13) . . . . ?
C15 C14 C16 O16 -143.06(10) . . . . ?
C12 C14 C16 C71 -132.25(10) . . . . ?
C15 C14 C16 C71 100.43(12) . . . . ?
C12 C14 C16 C61 103.15(12) . . . . ?
C15 C14 C16 C61 -24.17(14) . . . . ?
O11 C11 C21 C22 -147.24(14) . . . . ?
C31 C11 C21 C22 99.08(15) . . . . ?
C12 C11 C21 C22 -27.19(17) . . . . ?
O11 C11 C21 C26 30.72(17) . . . . ?
C31 C11 C21 C26 -82.95(15) . . . . ?
C12 C11 C21 C26 150.77(13) . . . . ?
C26 C21 C22 C23 -0.5(2) . . . . ?
C11 C21 C22 C23 177.49(15) . . . . ?
C21 C22 C23 C24 -0.8(3) . . . . ?
C22 C23 C24 C25 0.8(3) . . . . ?
C23 C24 C25 C26 0.6(4) . . . . ?
C24 C25 C26 C21 -2.0(3) . . . . ?
C22 C21 C26 C25 1.9(3) . . . . ?
C11 C21 C26 C25 -176.22(17) . . . . ?
O11 C11 C31 C36 39.51(15) . . . . ?
C21 C11 C31 C36 155.56(12) . . . . ?
C12 C11 C31 C36 -80.46(15) . . . . ?
O11 C11 C31 C32 -139.10(13) . . . . ?
C21 C11 C31 C32 -23.04(17) . . . . ?
C12 C11 C31 C32 100.94(15) . . . . ?
C36 C31 C32 C33 0.2(2) . . . . ?
C11 C31 C32 C33 178.83(14) . . . . ?
C31 C32 C33 C34 1.0(3) . . . . ?
C32 C33 C34 C35 -0.8(3) . . . . ?
C33 C34 C35 C36 -0.6(3) . . . . ?
C32 C31 C36 C35 -1.6(2) . . . . ?
C11 C31 C36 C35 179.73(13) . . . . ?
C34 C35 C36 C31 1.8(3) . . . . ?
C52 C13 C41 C42 -54.93(13) . . . . ?
C12 C13 C41 C42 57.29(14) . . . . ?
C52 C13 C41 C46 122.86(13) . . . . ?
C12 C13 C41 C46 -124.92(13) . . . . ?
C46 C41 C42 C43 2.34(19) . . . . ?
C13 C41 C42 C43 -179.71(12) . . . . ?
C46 C41 C42 C15 -179.40(11) . . . . ?
C13 C41 C42 C15 -1.45(15) . . . . ?
C51 C15 C42 C43 -125.59(14) . . . . ?
C14 C15 C42 C43 117.35(14) . . . . ?
C51 C15 C42 C41 56.30(13) . . . . ?
C14 C15 C42 C41 -60.76(13) . . . . ?
C41 C42 C43 C44 -1.6(2) . . . . ?
C15 C42 C43 C44 -179.55(13) . . . . ?
C42 C43 C44 C45 0.1(2) . . . . ?
C43 C44 C45 C46 0.6(3) . . . . ?
C44 C45 C46 C41 0.2(2) . . . . ?
C42 C41 C46 C45 -1.7(2) . . . . ?
C13 C41 C46 C45 -179.29(13) . . . . ?
C42 C15 C51 C56 123.38(14) . . . . ?
C14 C15 C51 C56 -124.78(13) . . . . ?
C42 C15 C51 C52 -53.34(13) . . . . ?
C14 C15 C51 C52 58.50(14) . . . . ?
C56 C51 C52 C53 0.06(19) . . . . ?
C15 C51 C52 C53 177.01(11) . . . . ?
C56 C51 C52 C13 -179.77(11) . . . . ?
C15 C51 C52 C13 -2.82(14) . . . . ?
C41 C13 C52 C53 -121.94(14) . . . . ?
C12 C13 C52 C53 120.59(13) . . . . ?
C41 C13 C52 C51 57.89(13) . . . . ?
C12 C13 C52 C51 -59.59(12) . . . . ?
C51 C52 C53 C54 -0.6(2) . . . . ?
C13 C52 C53 C54 179.21(13) . . . . ?
C52 C53 C54 C55 0.4(2) . . . . ?
C53 C54 C55 C56 0.4(3) . . . . ?
C54 C55 C56 C51 -0.9(2) . . . . ?
C52 C51 C56 C55 0.7(2) . . . . ?
C15 C51 C56 C55 -175.80(13) . . . . ?
O16 C16 C61 C62 34.10(16) . . . . ?
C71 C16 C61 C62 153.62(12) . . . . ?
C14 C16 C61 C62 -83.58(15) . . . . ?
O16 C16 C61 C66 -143.91(12) . . . . ?
C71 C16 C61 C66 -24.40(16) . . . . ?
C14 C16 C61 C66 98.40(14) . . . . ?
C66 C61 C62 C63 0.6(2) . . . . ?
C16 C61 C62 C63 -177.50(14) . . . . ?
C61 C62 C63 C64 0.3(3) . . . . ?
C62 C63 C64 C65 -1.3(3) . . . . ?
C63 C64 C65 C66 1.4(3) . . . . ?
C62 C61 C66 C65 -0.6(2) . . . . ?
C16 C61 C66 C65 177.46(14) . . . . ?
C64 C65 C66 C61 -0.4(3) . . . . ?
O16 C16 C71 C76 19.95(16) . . . . ?
C61 C16 C71 C76 -98.89(14) . . . . ?
C14 C16 C71 C76 134.31(12) . . . . ?
O16 C16 C71 C72 -158.07(12) . . . . ?
C61 C16 C71 C72 83.09(15) . . . . ?
C14 C16 C71 C72 -43.71(15) . . . . ?
C76 C71 C72 C73 -0.2(2) . . . . ?
C16 C71 C72 C73 177.92(14) . . . . ?
C71 C72 C73 C74 -1.3(3) . . . . ?
C72 C73 C74 C75 1.5(3) . . . . ?
C73 C74 C75 C76 -0.3(3) . . . . ?
C74 C75 C76 C71 -1.2(2) . . . . ?
C72 C71 C76 C75 1.4(2) . . . . ?
C16 C71 C76 C75 -176.67(13) . . . . ?

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
O11 H11 O16 0.82 1.88 2.6264(15) 150 . yes
O16 H16 N1 0.82 1.99 2.7258(15) 149 . yes
C76 H76 O16 0.93 2.41 2.7394(18) 101 . yes

_refine_diff_density_max         0.259
_refine_diff_density_min         -0.170
_refine_diff_density_rms         0.033


_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_42MPYRF
_database_code_depnum_ccdc_archive 'CCDC 2235784'
loop_
_audit_author_name
_audit_author_address
'Mino Caira'
;University of Cape Town
South Africa
;
_audit_update_record             
;
2023-01-12 deposited with the CCDC.	2023-02-28 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        
"1,1,1',1'-tetrakis(p-Chlorophenyl)-(9,10-ethanoanthracene-trans-11,12-diyl)dimethanol 2-methylpyridine clathrate'"
_chemical_name_common            none
_chemical_melting_point          'decomp. at 427 K'
_chemical_formula_moiety         'C42 H30 Cl4 O2, C6 H7 N'
_chemical_formula_sum            'C48 H37 Cl4 N O2'
_chemical_formula_weight         801.58

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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           70
_space_group_name_H-M_alt        'F d d d'
_space_group_name_Hall           '-F 2uv 2vw'

_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+1/4, -y+1/4, z'
'x, -y+1/4, -z+1/4'
'-x+1/4, y, -z+1/4'
'x, y+1/2, z+1/2'
'-x+1/4, -y+3/4, z+1/2'
'x, -y+3/4, -z+3/4'
'-x+1/4, y+1/2, -z+3/4'
'x+1/2, y, z+1/2'
'-x+3/4, -y+1/4, z+1/2'
'x+1/2, -y+1/4, -z+3/4'
'-x+3/4, y, -z+3/4'
'x+1/2, y+1/2, z'
'-x+3/4, -y+3/4, z'
'x+1/2, -y+3/4, -z+1/4'
'-x+3/4, y+1/2, -z+1/4'
'-x, -y, -z'
'x-1/4, y-1/4, -z'
'-x, y-1/4, z-1/4'
'x-1/4, -y, z-1/4'
'-x, -y+1/2, -z+1/2'
'x-1/4, y+1/4, -z+1/2'
'-x, y+1/4, z+1/4'
'x-1/4, -y+1/2, z+1/4'
'-x+1/2, -y, -z+1/2'
'x+1/4, y-1/4, -z+1/2'
'-x+1/2, y-1/4, z+1/4'
'x+1/4, -y, z+1/4'
'-x+1/2, -y+1/2, -z'
'x+1/4, y+1/4, -z'
'-x+1/2, y+1/4, z-1/4'
'x+1/4, -y+1/2, z-1/4'

_cell_length_a                   15.5845(13)
_cell_length_b                   24.9973(19)
_cell_length_c                   40.030(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     15595(2)
_cell_formula_units_Z            16
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    9982
_cell_measurement_theta_min      2.17
_cell_measurement_theta_max      28.13

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.366
_exptl_crystal_F_000             6656
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.140
_exptl_crystal_size_mid          0.130
_exptl_crystal_size_min          0.050
_exptl_absorpt_coefficient_mu    0.346
_shelx_estimated_absorpt_T_min   0.953
_shelx_estimated_absorpt_T_max   0.983
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6509
_exptl_absorpt_correction_T_max  0.6875
_exptl_absorpt_process_details   
;
 SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
 J. Appl. Cryst. 48 (2015) 3-10
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed tube'
_diffrn_measurement_device_type  'Bruker D8 VENTURE SCXRD diffractometer'
_diffrn_measurement_method       'omega-and phi-scans, width 1.0 deg.'
_diffrn_detector_area_resol_mean n/a
_diffrn_reflns_number            287793
_diffrn_reflns_av_unetI/netI     0.0170
_diffrn_reflns_av_R_equivalents  0.1041
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_k_min       -33
_diffrn_reflns_limit_k_max       33
_diffrn_reflns_limit_l_min       -53
_diffrn_reflns_limit_l_max       53
_diffrn_reflns_theta_min         2.035
_diffrn_reflns_theta_max         28.404
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             4876
_reflns_number_gt                4385
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Apex3 v2019.1-0, Bruker (2019).'
_computing_cell_refinement       
'SAINT V8.40A, Bruker AXS Inc.: Madison (WI), USA.'
_computing_data_reduction        
'SAINT V8.40A, Bruker AXS Inc.: Madison (WI), USA.'
_computing_structure_solution    'SHELXS-Version 2018/3 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    
'POV-Ray in interface X-Seed (LJ Barbour, 1999)'
_computing_publication_material  'PLATON (Spek, 1990)'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0424P)²+61.0605P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_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         4876
_refine_ls_number_parameters     254
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0570
_refine_ls_R_factor_gt           0.0515
_refine_ls_wR_factor_ref         0.1290
_refine_ls_wR_factor_gt          0.1252
_refine_ls_goodness_of_fit_ref   1.117
_refine_ls_restrained_S_all      1.117
_refine_ls_shift/su_max          0.011
_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
Cl1 Cl 0.53528(4) 0.32432(2) 0.82791(2) 0.04561(16) Uani 1 1 d . . . . .
O1 O 0.47528(8) 0.58788(5) 0.84240(3) 0.0284(3) Uani 1 1 d . . . . .
H1 H 0.466803 0.587638 0.822185 0.034 Uiso 1 1 calc R U . . .
C1 C 0.70800(14) 0.60334(9) 0.77574(5) 0.0381(5) Uani 1 1 d . . . . .
Cl2 Cl 0.58392(4) 0.55579(2) 1.00029(2) 0.04483(16) Uani 1 1 d . . . . .
C2 C 0.78091(16) 0.58040(11) 0.76194(6) 0.0475(6) Uani 1 1 d . . . . .
H2 H 0.789462 0.543602 0.762781 0.057 Uiso 1 1 calc R U . . .
C3 C 0.84154(17) 0.61407(13) 0.74665(6) 0.0562(7) Uani 1 1 d . . . . .
H3 H 0.890784 0.599368 0.737270 0.067 Uiso 1 1 calc R U . . .
C4 C 0.82897(17) 0.66851(12) 0.74538(6) 0.0548(7) Uani 1 1 d . . . . .
H4 H 0.869507 0.690108 0.734947 0.066 Uiso 1 1 calc R U . . .
C5 C 0.75640(16) 0.69163(11) 0.75950(5) 0.0460(6) Uani 1 1 d . . . . .
H5 H 0.748220 0.728463 0.758687 0.055 Uiso 1 1 calc R U . . .
C6 C 0.69608(14) 0.65863(9) 0.77490(5) 0.0377(5) Uani 1 1 d . . . . .
C7 C 0.63487(13) 0.57367(8) 0.79242(5) 0.0339(4) Uani 1 1 d . . . . .
H7 H 0.642626 0.534815 0.791143 0.041 Uiso 1 1 calc R U . . .
C8 C 0.63003(12) 0.59372(7) 0.82987(4) 0.0259(3) Uani 1 1 d . . . . .
H8 H 0.684690 0.585029 0.840692 0.031 Uiso 1 1 calc R U . . .
C9 C 0.55676(11) 0.56404(7) 0.84941(4) 0.0243(3) Uani 1 1 d . . . . .
C10 C 0.55379(11) 0.50379(7) 0.84120(4) 0.0263(3) Uani 1 1 d . . . . .
C11 C 0.62673(12) 0.47174(8) 0.84330(5) 0.0313(4) Uani 1 1 d . . . . .
H11 H 0.679532 0.487504 0.847802 0.038 Uiso 1 1 calc R U . . .
C12 C 0.62215(14) 0.41664(8) 0.83878(5) 0.0339(4) Uani 1 1 d . . . . .
H12 H 0.671352 0.395705 0.840120 0.041 Uiso 1 1 calc R U . . .
C13 C 0.54335(15) 0.39347(8) 0.83226(5) 0.0353(4) Uani 1 1 d . . . . .
C14 C 0.47124(16) 0.42435(9) 0.82943(7) 0.0468(6) Uani 1 1 d . . . . .
H14 H 0.418852 0.408493 0.824359 0.056 Uiso 1 1 calc R U . . .
C15 C 0.47607(13) 0.47936(8) 0.83413(6) 0.0389(5) Uani 1 1 d . . . . .
H15 H 0.426600 0.499997 0.832496 0.047 Uiso 1 1 calc R U . . .
C16 C 0.56620(11) 0.56596(7) 0.88752(4) 0.0242(3) Uani 1 1 d . . . . .
C17 C 0.49275(12) 0.56800(8) 0.90734(5) 0.0300(4) Uani 1 1 d . . . . .
H17 H 0.439301 0.571733 0.897271 0.036 Uiso 1 1 calc R U . . .
C18 C 0.49822(13) 0.56452(8) 0.94193(5) 0.0335(4) Uani 1 1 d . . . . .
H18 H 0.448758 0.565850 0.954894 0.040 Uiso 1 1 calc R U . . .
C19 C 0.57743(13) 0.55909(7) 0.95690(5) 0.0312(4) Uani 1 1 d . . . . .
C20 C 0.65122(13) 0.55673(7) 0.93795(5) 0.0309(4) Uani 1 1 d . . . . .
H20 H 0.704409 0.552966 0.948215 0.037 Uiso 1 1 calc R U . . .
C21 C 0.64539(11) 0.56004(7) 0.90338(5) 0.0281(4) Uani 1 1 d . . . . .
H21 H 0.695115 0.558269 0.890589 0.034 Uiso 1 1 calc R U . . .
N22 N 0.625000 0.69411(17) 0.625000 0.0934(14) Uani 1 2 d S T P . .
C23 C 0.6246(3) 0.72172(15) 0.65413(7) 0.0976(13) Uani 1 1 d D . . . .
C24 C 0.6241(2) 0.77697(19) 0.65502(12) 0.0942(13) Uani 1 1 d . . . . .
H24 H 0.623085 0.796503 0.674794 0.113 Uiso 1 1 calc R U . . .
C25 C 0.625000 0.7996(2) 0.625000 0.0821(16) Uani 1 2 d S T P . .
H25 H 0.625003 0.836779 0.625000 0.099 Uiso 1 2 calc R U P . .
C26 C 0.6242(8) 0.68665(17) 0.68239(11) 0.134(4) Uiso 0.5 1 d D . P . .
H26A H 0.581232 0.698206 0.697995 0.200 Uiso 0.5 1 calc R U P . .
H26B H 0.679459 0.687335 0.692975 0.200 Uiso 0.5 1 calc R U P . .
H26C H 0.611571 0.650883 0.675172 0.200 Uiso 0.5 1 calc R U P . .
H23 H 0.626(3) 0.70171(14) 0.67371(7) 0.160 Uiso 0.5 1 d D U P . .


_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
Cl1 C13 1.742(2) . ?
O1 C9 1.430(2) . ?
O1 H1 0.8200 . ?
C1 C2 1.388(3) . ?
C1 C6 1.395(3) . ?
C1 C7 1.515(3) . ?
Cl2 C19 1.7421(19) . ?
C2 C3 1.406(3) . ?
C2 H2 0.9300 . ?
C3 C4 1.376(4) . ?
C3 H3 0.9300 . ?
C4 C5 1.390(4) . ?
C4 H4 0.9300 . ?
C5 C6 1.394(3) . ?
C5 H5 0.9300 . ?
C6 C7 1.510(3) 2_665 ?
C7 C8 1.582(2) . ?
C7 H7 0.9800 . ?
C8 C9 1.570(2) . ?
C8 C8 1.572(4) 2_665 ?
C8 H8 0.9800 . ?
C9 C16 1.534(2) . ?
C9 C10 1.542(2) . ?
C10 C15 1.386(3) . ?
C10 C11 1.393(3) . ?
C11 C12 1.391(3) . ?
C11 H11 0.9300 . ?
C12 C13 1.383(3) . ?
C12 H12 0.9300 . ?
C13 C14 1.368(3) . ?
C14 C15 1.390(3) . ?
C14 H14 0.9300 . ?
C15 H15 0.9300 . ?
C16 C17 1.394(2) . ?
C16 C21 1.396(2) . ?
C17 C18 1.390(3) . ?
C17 H17 0.9300 . ?
C18 C19 1.379(3) . ?
C18 H18 0.9300 . ?
C19 C20 1.379(3) . ?
C20 C21 1.389(3) . ?
C20 H20 0.9300 . ?
C21 H21 0.9300 . ?
N22 C23 1.355(4) 4_656 ?
N22 C23 1.355(4) . ?
C23 C24 1.382(6) . ?
C23 C26 1.431(4) . ?
C23 H23 0.93000(14) . ?
C24 C25 1.328(5) . ?
C24 H24 0.9300 . ?
C25 H25 0.9300 . ?
C26 H26A 0.9600 . ?
C26 H26B 0.9600 . ?
C26 H26C 0.9600 . ?
C26 H23 0.5130(5) . ?

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
C9 O1 H1 109.5 . . ?
C2 C1 C6 120.6(2) . . ?
C2 C1 C7 126.1(2) . . ?
C6 C1 C7 113.3(2) . . ?
C1 C2 C3 118.4(3) . . ?
C1 C2 H2 120.8 . . ?
C3 C2 H2 120.8 . . ?
C4 C3 C2 120.8(3) . . ?
C4 C3 H3 119.6 . . ?
C2 C3 H3 119.6 . . ?
C3 C4 C5 120.8(2) . . ?
C3 C4 H4 119.6 . . ?
C5 C4 H4 119.6 . . ?
C4 C5 C6 118.8(2) . . ?
C4 C5 H5 120.6 . . ?
C6 C5 H5 120.6 . . ?
C5 C6 C1 120.5(2) . . ?
C5 C6 C7 126.5(2) . 2_665 ?
C1 C6 C7 112.99(17) . 2_665 ?
C6 C7 C1 106.28(17) 2_665 . ?
C6 C7 C8 107.90(17) 2_665 . ?
C1 C7 C8 107.36(15) . . ?
C6 C7 H7 111.7 2_665 . ?
C1 C7 H7 111.7 . . ?
C8 C7 H7 111.7 . . ?
C9 C8 C8 113.42(17) . 2_665 ?
C9 C8 C7 110.90(14) . . ?
C8 C8 C7 108.66(10) 2_665 . ?
C9 C8 H8 107.9 . . ?
C8 C8 H8 107.9 2_665 . ?
C7 C8 H8 107.9 . . ?
O1 C9 C16 105.50(14) . . ?
O1 C9 C10 109.78(13) . . ?
C16 C9 C10 104.20(14) . . ?
O1 C9 C8 110.55(14) . . ?
C16 C9 C8 114.27(14) . . ?
C10 C9 C8 112.15(14) . . ?
C15 C10 C11 118.17(18) . . ?
C15 C10 C9 120.01(17) . . ?
C11 C10 C9 121.61(16) . . ?
C12 C11 C10 121.30(18) . . ?
C12 C11 H11 119.3 . . ?
C10 C11 H11 119.3 . . ?
C13 C12 C11 119.02(19) . . ?
C13 C12 H12 120.5 . . ?
C11 C12 H12 120.5 . . ?
C14 C13 C12 120.58(18) . . ?
C14 C13 Cl1 119.49(16) . . ?
C12 C13 Cl1 119.92(17) . . ?
C13 C14 C15 120.2(2) . . ?
C13 C14 H14 119.9 . . ?
C15 C14 H14 119.9 . . ?
C10 C15 C14 120.7(2) . . ?
C10 C15 H15 119.6 . . ?
C14 C15 H15 119.6 . . ?
C17 C16 C21 118.11(17) . . ?
C17 C16 C9 119.25(16) . . ?
C21 C16 C9 122.29(16) . . ?
C18 C17 C16 120.95(18) . . ?
C18 C17 H17 119.5 . . ?
C16 C17 H17 119.5 . . ?
C19 C18 C17 119.61(18) . . ?
C19 C18 H18 120.2 . . ?
C17 C18 H18 120.2 . . ?
C20 C19 C18 120.78(17) . . ?
C20 C19 Cl2 119.87(16) . . ?
C18 C19 Cl2 119.34(15) . . ?
C19 C20 C21 119.39(18) . . ?
C19 C20 H20 120.3 . . ?
C21 C20 H20 120.3 . . ?
C20 C21 C16 121.15(17) . . ?
C20 C21 H21 119.4 . . ?
C16 C21 H21 119.4 . . ?
C23 N22 C23 118.8(4) 4_656 . ?
N22 C23 C24 122.1(3) . . ?
N22 C23 C26 111.6(4) . . ?
C24 C23 C26 126.3(4) . . ?
N22 C23 H23 116.8(4) . . ?
C24 C23 H23 121.1(5) . . ?
C25 C24 C23 113.7(4) . . ?
C25 C24 H24 123.2 . . ?
C23 C24 H24 123.2 . . ?
C24 C25 C24 129.6(6) . 4_656 ?
C24 C25 H25 115.2 . . ?
C24 C25 H25 115.2 4_656 . ?
C23 C26 H26A 109.5 . . ?
C23 C26 H26B 109.5 . . ?
H26A C26 H26B 109.5 . . ?
C23 C26 H26C 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
H26A C26 H23 104.7 . . ?
H26B C26 H23 104.0 . . ?
H26C C26 H23 119.3 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 C1 C2 C3 -1.1(3) . . . . ?
C7 C1 C2 C3 178.4(2) . . . . ?
C1 C2 C3 C4 0.0(4) . . . . ?
C2 C3 C4 C5 0.7(4) . . . . ?
C3 C4 C5 C6 -0.3(3) . . . . ?
C4 C5 C6 C1 -0.8(3) . . . . ?
C4 C5 C6 C7 178.0(2) . . . 2_665 ?
C2 C1 C6 C5 1.5(3) . . . . ?
C7 C1 C6 C5 -178.08(18) . . . . ?
C2 C1 C6 C7 -177.49(19) . . . 2_665 ?
C7 C1 C6 C7 3.0(2) . . . 2_665 ?
C2 C1 C7 C6 -126.0(2) . . . 2_665 ?
C6 C1 C7 C6 53.55(19) . . . 2_665 ?
C2 C1 C7 C8 118.8(2) . . . . ?
C6 C1 C7 C8 -61.7(2) . . . . ?
C6 C7 C8 C9 66.99(19) 2_665 . . . ?
C1 C7 C8 C9 -178.83(17) . . . . ?
C6 C7 C8 C8 -58.3(2) 2_665 . . 2_665 ?
C1 C7 C8 C8 55.9(2) . . . 2_665 ?
C8 C8 C9 O1 41.59(17) 2_665 . . . ?
C7 C8 C9 O1 -81.00(18) . . . . ?
C8 C8 C9 C16 -77.23(18) 2_665 . . . ?
C7 C8 C9 C16 160.17(16) . . . . ?
C8 C8 C9 C10 164.47(13) 2_665 . . . ?
C7 C8 C9 C10 41.9(2) . . . . ?
O1 C9 C10 C15 -10.3(2) . . . . ?
C16 C9 C10 C15 102.27(19) . . . . ?
C8 C9 C10 C15 -133.63(18) . . . . ?
O1 C9 C10 C11 174.96(16) . . . . ?
C16 C9 C10 C11 -72.5(2) . . . . ?
C8 C9 C10 C11 51.6(2) . . . . ?
C15 C10 C11 C12 -0.6(3) . . . . ?
C9 C10 C11 C12 174.18(17) . . . . ?
C10 C11 C12 C13 -0.3(3) . . . . ?
C11 C12 C13 C14 1.7(3) . . . . ?
C11 C12 C13 Cl1 -177.83(15) . . . . ?
C12 C13 C14 C15 -2.0(4) . . . . ?
Cl1 C13 C14 C15 177.50(19) . . . . ?
C11 C10 C15 C14 0.3(3) . . . . ?
C9 C10 C15 C14 -174.6(2) . . . . ?
C13 C14 C15 C10 1.0(4) . . . . ?
O1 C9 C16 C17 24.8(2) . . . . ?
C10 C9 C16 C17 -90.84(19) . . . . ?
C8 C9 C16 C17 146.43(17) . . . . ?
O1 C9 C16 C21 -162.17(16) . . . . ?
C10 C9 C16 C21 82.21(19) . . . . ?
C8 C9 C16 C21 -40.5(2) . . . . ?
C21 C16 C17 C18 0.3(3) . . . . ?
C9 C16 C17 C18 173.68(17) . . . . ?
C16 C17 C18 C19 0.1(3) . . . . ?
C17 C18 C19 C20 -0.4(3) . . . . ?
C17 C18 C19 Cl2 179.03(15) . . . . ?
C18 C19 C20 C21 0.2(3) . . . . ?
Cl2 C19 C20 C21 -179.25(14) . . . . ?
C19 C20 C21 C16 0.3(3) . . . . ?
C17 C16 C21 C20 -0.6(3) . . . . ?
C9 C16 C21 C20 -173.69(16) . . . . ?
C23 N22 C23 C24 0.4(3) 4_656 . . . ?
C23 N22 C23 C26 179.9(7) 4_656 . . . ?
N22 C23 C24 C25 -0.8(5) . . . . ?
C26 C23 C24 C25 179.8(7) . . . . ?
C23 C24 C25 C24 0.4(3) . . . 4_656 ?

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
C8 H8 O1 0.98 2.38 2.874(2) 110.2 2_665 yes

_refine_diff_density_max         0.834
_refine_diff_density_min         -0.448
_refine_diff_density_rms         0.056


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: 2-methylpyridine'
