# 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_PYR_D
_database_code_depnum_ccdc_archive 'CCDC 2218843'
loop_
_audit_author_name
_audit_author_address
'Mino Caira'
;University of Cape Town
South Africa
;
_audit_update_record             
;
2022-11-10 deposited with the CCDC.	2023-10-20 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        
"N,N'-bis(5-phenyl-5H-dibenzo[a,d][7]annulen-5-yl)ethane-1,2-diamine pyridine clathrate"
_chemical_name_common            none
_chemical_melting_point          'onset of decomp. 328 K'
_chemical_formula_moiety         '(C44 H36 N2), 2(C5 H5 N)'
_chemical_formula_sum            'C54 H46 N4'
_chemical_formula_weight         750.95

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'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

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

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   9.0392(4)
_cell_length_b                   9.0518(3)
_cell_length_c                   13.7313(6)
_cell_angle_alpha                76.2020(10)
_cell_angle_beta                 74.8830(10)
_cell_angle_gamma                67.2250(10)
_cell_volume                     988.05(7)
_cell_formula_units_Z            1
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    9903
_cell_measurement_theta_min      2.47
_cell_measurement_theta_max      30.75

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.262
_exptl_crystal_F_000             398
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.320
_exptl_crystal_size_mid          0.250
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    0.074
_shelx_estimated_absorpt_T_min   0.977
_shelx_estimated_absorpt_T_max   0.993
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.962
_exptl_absorpt_correction_T_max  0.993
_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            57670
_diffrn_reflns_av_unetI/netI     0.0401
_diffrn_reflns_av_R_equivalents  0.0600
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         2.470
_diffrn_reflns_theta_max         31.698
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.961
_diffrn_measured_fraction_theta_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.961
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.961
_diffrn_reflns_point_group_measured_fraction_full 0.994
_reflns_number_total             6435
_reflns_number_gt                4672
_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)+(0.0439P)²+0.3994P] 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         6435
_refine_ls_number_parameters     266
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0838
_refine_ls_R_factor_gt           0.0476
_refine_ls_wR_factor_ref         0.1300
_refine_ls_wR_factor_gt          0.1062
_refine_ls_goodness_of_fit_ref   1.082
_refine_ls_restrained_S_all      1.082
_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
C1 C 0.59843(14) 0.62866(13) 0.26902(8) 0.0181(2) Uani 1 1 d . . . . .
C2 C 0.65107(16) 0.71127(15) 0.04045(9) 0.0244(2) Uani 1 1 d . . . . .
H2 H 0.598354 0.761497 -0.016504 0.029 Uiso 1 1 calc R U . . .
C3 C 0.71563(16) 0.54910(16) 0.05550(9) 0.0252(3) Uani 1 1 d . . . . .
H3 H 0.705403 0.494177 0.008022 0.030 Uiso 1 1 calc R U . . .
C4 C 0.64163(14) 0.77932(14) 0.21162(9) 0.0196(2) Uani 1 1 d . . . . .
C5 C 0.67211(15) 0.87764(15) 0.26268(9) 0.0236(2) Uani 1 1 d . . . . .
H5 H 0.668591 0.849938 0.334274 0.028 Uiso 1 1 calc R U . . .
C6 C 0.70763(17) 1.01579(16) 0.21051(10) 0.0283(3) Uani 1 1 d . . . . .
H6 H 0.730779 1.079642 0.246322 0.034 Uiso 1 1 calc R U . . .
C7 C 0.70924(18) 1.06023(16) 0.10639(11) 0.0318(3) Uani 1 1 d . . . . .
H7 H 0.728514 1.156923 0.071166 0.038 Uiso 1 1 calc R U . . .
C8 C 0.68246(17) 0.96219(16) 0.05446(10) 0.0280(3) Uani 1 1 d . . . . .
H8 H 0.682737 0.993220 -0.016720 0.034 Uiso 1 1 calc R U . . .
C9 C 0.65483(15) 0.81777(14) 0.10434(9) 0.0222(2) Uani 1 1 d . . . . .
C10 C 0.75381(14) 0.48530(13) 0.23947(9) 0.0194(2) Uani 1 1 d . . . . .
C11 C 0.85535(15) 0.39380(15) 0.30963(9) 0.0230(2) Uani 1 1 d . . . . .
H11 H 0.827325 0.420318 0.376539 0.028 Uiso 1 1 calc R U . . .
C12 C 0.99653(16) 0.26477(15) 0.28352(10) 0.0274(3) Uani 1 1 d . . . . .
H12 H 1.064107 0.204027 0.332337 0.033 Uiso 1 1 calc R U . . .
C13 C 1.03883(16) 0.22463(16) 0.18616(11) 0.0299(3) Uani 1 1 d . . . . .
H13 H 1.134117 0.135004 0.168552 0.036 Uiso 1 1 calc R U . . .
C14 C 0.94165(16) 0.31570(15) 0.11476(10) 0.0273(3) Uani 1 1 d . . . . .
H14 H 0.970881 0.287460 0.048243 0.033 Uiso 1 1 calc R U . . .
C15 C 0.80069(15) 0.44901(14) 0.13887(9) 0.0221(2) Uani 1 1 d . . . . .
N16 N 0.56566(13) 0.62928(12) 0.38051(7) 0.0198(2) Uani 1 1 d . . . . .
C17 C 0.49098(15) 0.51150(14) 0.44468(8) 0.0211(2) Uani 1 1 d . . . . .
H17A H 0.544699 0.406251 0.419038 0.025 Uiso 1 1 calc R U . . .
H17B H 0.373732 0.550773 0.440972 0.025 Uiso 1 1 calc R U . . .
C18 C 0.44649(14) 0.62623(14) 0.23847(8) 0.0196(2) Uani 1 1 d . . . . .
C19 C 0.43169(16) 0.48246(15) 0.22990(9) 0.0238(2) Uani 1 1 d . . . . .
H19 H 0.520086 0.383210 0.238558 0.029 Uiso 1 1 calc R U . . .
C20 C 0.28926(17) 0.48209(17) 0.20884(10) 0.0297(3) Uani 1 1 d . . . . .
H20 H 0.281434 0.382846 0.203296 0.036 Uiso 1 1 calc R U . . .
C21 C 0.15886(17) 0.62550(19) 0.19591(10) 0.0327(3) Uani 1 1 d . . . . .
H21 H 0.062061 0.625339 0.180964 0.039 Uiso 1 1 calc R U . . .
C22 C 0.17155(17) 0.76943(18) 0.20508(11) 0.0312(3) Uani 1 1 d . . . . .
H22 H 0.083001 0.868468 0.196186 0.037 Uiso 1 1 calc R U . . .
C23 C 0.31339(15) 0.76941(15) 0.22725(9) 0.0247(2) Uani 1 1 d . . . . .
H23 H 0.319560 0.868358 0.234846 0.030 Uiso 1 1 calc R U . . .
N24 N 0.33295(16) 0.98627(15) 0.44707(10) 0.0371(3) Uani 1 1 d . . . . .
C25 C 0.2068(2) 0.96808(19) 0.51893(12) 0.0384(3) Uani 1 1 d . . . . .
H25 H 0.198762 0.863053 0.538437 0.046 Uiso 1 1 calc R U . . .
C26 C 0.0873(2) 1.0924(2) 0.56657(12) 0.0392(3) Uani 1 1 d . . . . .
H26 H -0.000045 1.072848 0.617289 0.047 Uiso 1 1 calc R U . . .
C27 C 0.0970(2) 1.24557(19) 0.53926(12) 0.0381(3) Uani 1 1 d . . . . .
H27 H 0.016661 1.333811 0.570604 0.046 Uiso 1 1 calc R U . . .
C28 C 0.2265(2) 1.26749(19) 0.46514(12) 0.0372(3) Uani 1 1 d . . . . .
H28 H 0.237071 1.371388 0.444240 0.045 Uiso 1 1 calc R U . . .
C29 C 0.34021(19) 1.13550(19) 0.42207(12) 0.0371(3) Uani 1 1 d . . . . .
H29 H 0.429174 1.151793 0.371486 0.044 Uiso 1 1 calc R U . . .
H16 H 0.501(2) 0.731(2) 0.3933(12) 0.030(4) Uiso 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 N16 1.4825(14) . ?
C1 C10 1.5375(16) . ?
C1 C4 1.5403(15) . ?
C1 C18 1.5462(16) . ?
C2 C3 1.3390(18) . ?
C2 C9 1.4643(17) . ?
C2 H2 0.9500 . ?
C3 C15 1.4654(17) . ?
C3 H3 0.9500 . ?
C4 C5 1.3956(16) . ?
C4 C9 1.4147(16) . ?
C5 C6 1.3941(17) . ?
C5 H5 0.9500 . ?
C6 C7 1.3877(19) . ?
C6 H6 0.9500 . ?
C7 C8 1.383(2) . ?
C7 H7 0.9500 . ?
C8 C9 1.4061(16) . ?
C8 H8 0.9500 . ?
C10 C11 1.3959(16) . ?
C10 C15 1.4139(16) . ?
C11 C12 1.3887(18) . ?
C11 H11 0.9500 . ?
C12 C13 1.387(2) . ?
C12 H12 0.9500 . ?
C13 C14 1.3841(19) . ?
C13 H13 0.9500 . ?
C14 C15 1.4033(17) . ?
C14 H14 0.9500 . ?
N16 C17 1.4723(14) . ?
N16 H16 0.908(16) . ?
C17 C17 1.526(2) 2_666 ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C18 C19 1.3933(16) . ?
C18 C23 1.3946(17) . ?
C19 C20 1.3925(18) . ?
C19 H19 0.9500 . ?
C20 C21 1.386(2) . ?
C20 H20 0.9500 . ?
C21 C22 1.388(2) . ?
C21 H21 0.9500 . ?
C22 C23 1.3928(18) . ?
C22 H22 0.9500 . ?
C23 H23 0.9500 . ?
N24 C29 1.3351(19) . ?
N24 C25 1.335(2) . ?
C25 C26 1.379(2) . ?
C25 H25 0.9500 . ?
C26 C27 1.378(2) . ?
C26 H26 0.9500 . ?
C27 C28 1.381(2) . ?
C27 H27 0.9500 . ?
C28 C29 1.379(2) . ?
C28 H28 0.9500 . ?
C29 H29 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N16 C1 C10 109.87(9) . . ?
N16 C1 C4 109.34(9) . . ?
C10 C1 C4 104.03(9) . . ?
N16 C1 C18 109.37(9) . . ?
C10 C1 C18 113.00(9) . . ?
C4 C1 C18 111.09(9) . . ?
C3 C2 C9 125.54(11) . . ?
C3 C2 H2 117.2 . . ?
C9 C2 H2 117.2 . . ?
C2 C3 C15 125.66(12) . . ?
C2 C3 H3 117.2 . . ?
C15 C3 H3 117.2 . . ?
C5 C4 C9 118.78(10) . . ?
C5 C4 C1 121.54(10) . . ?
C9 C4 C1 119.67(10) . . ?
C6 C5 C4 121.18(11) . . ?
C6 C5 H5 119.4 . . ?
C4 C5 H5 119.4 . . ?
C7 C6 C5 120.14(12) . . ?
C7 C6 H6 119.9 . . ?
C5 C6 H6 119.9 . . ?
C8 C7 C6 119.26(12) . . ?
C8 C7 H7 120.4 . . ?
C6 C7 H7 120.4 . . ?
C7 C8 C9 121.67(12) . . ?
C7 C8 H8 119.2 . . ?
C9 C8 H8 119.2 . . ?
C8 C9 C4 118.67(11) . . ?
C8 C9 C2 117.33(11) . . ?
C4 C9 C2 123.90(11) . . ?
C11 C10 C15 118.75(11) . . ?
C11 C10 C1 120.81(10) . . ?
C15 C10 C1 120.36(10) . . ?
C12 C11 C10 121.27(12) . . ?
C12 C11 H11 119.4 . . ?
C10 C11 H11 119.4 . . ?
C13 C12 C11 119.97(12) . . ?
C13 C12 H12 120.0 . . ?
C11 C12 H12 120.0 . . ?
C14 C13 C12 119.72(12) . . ?
C14 C13 H13 120.1 . . ?
C12 C13 H13 120.1 . . ?
C13 C14 C15 121.17(12) . . ?
C13 C14 H14 119.4 . . ?
C15 C14 H14 119.4 . . ?
C14 C15 C10 118.99(11) . . ?
C14 C15 C3 117.32(11) . . ?
C10 C15 C3 123.58(11) . . ?
C17 N16 C1 115.46(9) . . ?
C17 N16 H16 109.4(10) . . ?
C1 N16 H16 108.6(10) . . ?
N16 C17 C17 110.25(12) . 2_666 ?
N16 C17 H17A 109.6 . . ?
C17 C17 H17A 109.6 2_666 . ?
N16 C17 H17B 109.6 . . ?
C17 C17 H17B 109.6 2_666 . ?
H17A C17 H17B 108.1 . . ?
C19 C18 C23 118.08(11) . . ?
C19 C18 C1 122.02(10) . . ?
C23 C18 C1 119.68(10) . . ?
C20 C19 C18 120.98(12) . . ?
C20 C19 H19 119.5 . . ?
C18 C19 H19 119.5 . . ?
C21 C20 C19 120.46(12) . . ?
C21 C20 H20 119.8 . . ?
C19 C20 H20 119.8 . . ?
C20 C21 C22 119.12(12) . . ?
C20 C21 H21 120.4 . . ?
C22 C21 H21 120.4 . . ?
C21 C22 C23 120.37(13) . . ?
C21 C22 H22 119.8 . . ?
C23 C22 H22 119.8 . . ?
C22 C23 C18 120.96(12) . . ?
C22 C23 H23 119.5 . . ?
C18 C23 H23 119.5 . . ?
C29 N24 C25 116.17(14) . . ?
N24 C25 C26 124.02(14) . . ?
N24 C25 H25 118.0 . . ?
C26 C25 H25 118.0 . . ?
C27 C26 C25 118.78(14) . . ?
C27 C26 H26 120.6 . . ?
C25 C26 H26 120.6 . . ?
C26 C27 C28 118.30(15) . . ?
C26 C27 H27 120.9 . . ?
C28 C27 H27 120.9 . . ?
C29 C28 C27 118.68(14) . . ?
C29 C28 H28 120.7 . . ?
C27 C28 H28 120.7 . . ?
N24 C29 C28 124.05(14) . . ?
N24 C29 H29 118.0 . . ?
C28 C29 H29 118.0 . . ?

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
C9 C2 C3 C15 0.4(2) . . . . ?
N16 C1 C4 C5 10.62(15) . . . . ?
C10 C1 C4 C5 -106.71(12) . . . . ?
C18 C1 C4 C5 131.42(11) . . . . ?
N16 C1 C4 C9 -170.91(10) . . . . ?
C10 C1 C4 C9 71.76(13) . . . . ?
C18 C1 C4 C9 -50.11(14) . . . . ?
C9 C4 C5 C6 2.94(18) . . . . ?
C1 C4 C5 C6 -178.58(11) . . . . ?
C4 C5 C6 C7 1.6(2) . . . . ?
C5 C6 C7 C8 -2.9(2) . . . . ?
C6 C7 C8 C9 -0.5(2) . . . . ?
C7 C8 C9 C4 5.00(19) . . . . ?
C7 C8 C9 C2 -171.49(13) . . . . ?
C5 C4 C9 C8 -6.12(17) . . . . ?
C1 C4 C9 C8 175.37(11) . . . . ?
C5 C4 C9 C2 170.13(12) . . . . ?
C1 C4 C9 C2 -8.38(18) . . . . ?
C3 C2 C9 C8 140.19(14) . . . . ?
C3 C2 C9 C4 -36.1(2) . . . . ?
N16 C1 C10 C11 -9.90(14) . . . . ?
C4 C1 C10 C11 107.05(11) . . . . ?
C18 C1 C10 C11 -132.35(11) . . . . ?
N16 C1 C10 C15 173.32(10) . . . . ?
C4 C1 C10 C15 -69.72(13) . . . . ?
C18 C1 C10 C15 50.87(14) . . . . ?
C15 C10 C11 C12 -2.74(17) . . . . ?
C1 C10 C11 C12 -179.56(11) . . . . ?
C10 C11 C12 C13 -0.06(19) . . . . ?
C11 C12 C13 C14 1.33(19) . . . . ?
C12 C13 C14 C15 0.26(19) . . . . ?
C13 C14 C15 C10 -3.06(18) . . . . ?
C13 C14 C15 C3 173.30(12) . . . . ?
C11 C10 C15 C14 4.23(17) . . . . ?
C1 C10 C15 C14 -178.93(10) . . . . ?
C11 C10 C15 C3 -171.89(11) . . . . ?
C1 C10 C15 C3 4.95(17) . . . . ?
C2 C3 C15 C14 -138.87(14) . . . . ?
C2 C3 C15 C10 37.31(19) . . . . ?
C10 C1 N16 C17 -78.21(12) . . . . ?
C4 C1 N16 C17 168.20(10) . . . . ?
C18 C1 N16 C17 46.36(13) . . . . ?
C1 N16 C17 C17 163.47(12) . . . 2_666 ?
N16 C1 C18 C19 -95.39(12) . . . . ?
C10 C1 C18 C19 27.33(14) . . . . ?
C4 C1 C18 C19 143.82(11) . . . . ?
N16 C1 C18 C23 79.09(12) . . . . ?
C10 C1 C18 C23 -158.18(10) . . . . ?
C4 C1 C18 C23 -41.70(14) . . . . ?
C23 C18 C19 C20 1.18(17) . . . . ?
C1 C18 C19 C20 175.75(11) . . . . ?
C18 C19 C20 C21 0.02(19) . . . . ?
C19 C20 C21 C22 -0.5(2) . . . . ?
C20 C21 C22 C23 -0.2(2) . . . . ?
C21 C22 C23 C18 1.4(2) . . . . ?
C19 C18 C23 C22 -1.89(18) . . . . ?
C1 C18 C23 C22 -176.59(11) . . . . ?
C29 N24 C25 C26 0.3(2) . . . . ?
N24 C25 C26 C27 0.0(3) . . . . ?
C25 C26 C27 C28 0.0(2) . . . . ?
C26 C27 C28 C29 -0.1(2) . . . . ?
C25 N24 C29 C28 -0.4(2) . . . . ?
C27 C28 C29 N24 0.4(2) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
N16 H16 N24 0.908(16) 2.390(17) 3.2932(17) 173.4(14) . yes

_refine_diff_density_max         0.328
_refine_diff_density_min         -0.269
_refine_diff_density_rms         0.062


_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_ma171_tw
_database_code_depnum_ccdc_archive 'CCDC 2241128'
loop_
_audit_author_name
_audit_author_address
'Eric Hosten'
;Nelson Mandela University
South Africa
;
_audit_update_record             
;
2023-02-10 deposited with the CCDC.	2023-10-20 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        
;
N,N'-Bis(5-phenyl-10,11-dihydro-5-dibenzo[a,d]cycloheptenyl)ethylenediamine
;
_chemical_name_common            ?
_chemical_melting_point          349.65
_chemical_formula_moiety         'C44 H40 N2, 2(C5 H5 N)'
_chemical_formula_sum            'C54 H50 N4'
_chemical_formula_weight         754.98

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'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

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

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.9716(5)
_cell_length_b                   9.2886(5)
_cell_length_c                   13.8221(8)
_cell_angle_alpha                75.212(3)
_cell_angle_beta                 76.005(3)
_cell_angle_gamma                66.684(3)
_cell_volume                     1009.80(10)
_cell_formula_units_Z            1
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    9903
_cell_measurement_theta_min      2.43
_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    1.242
_exptl_crystal_F_000             402
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.951
_exptl_crystal_size_mid          0.426
_exptl_crystal_size_min          0.076
_exptl_absorpt_coefficient_mu    0.072
_shelx_estimated_absorpt_T_min   0.934
_shelx_estimated_absorpt_T_max   0.995
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.676861
_exptl_absorpt_correction_T_max  0.745684
_exptl_absorpt_process_details   'TWINABS-2012/1 (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            40261
_diffrn_reflns_av_unetI/netI     0.0272
_diffrn_reflns_av_R_equivalents  0.0311
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.427
_diffrn_reflns_theta_max         28.360
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_point_group_measured_fraction_full 0.995
_reflns_number_total             5002
_reflns_number_gt                4112
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 _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 nitrogen-bound H atoms were located on a difference map and refined freely.

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

Refined as a 2-component twin.,Twin
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0319P)²+0.2684P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_extinction_coef       0.014(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         5002
_refine_ls_number_parameters     268
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0580
_refine_ls_R_factor_gt           0.0406
_refine_ls_wR_factor_ref         0.0974
_refine_ls_wR_factor_gt          0.0875
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_restrained_S_all      1.047
_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
N1 N 0.62730(16) 0.56258(16) 0.37990(9) 0.0281(3) Uani 1 1 d . . . . .
N4 N -0.0156(2) 0.3316(2) 0.44353(15) 0.0608(5) Uani 1 1 d . . . . .
C1 C 0.62479(17) 0.59340(17) 0.26912(10) 0.0254(3) Uani 1 1 d . . . . .
C2 C 0.5099(2) 0.4912(2) 0.44532(11) 0.0300(3) Uani 1 1 d . . . . .
H2A H 0.548581 0.379183 0.441313 0.036 Uiso 1 1 calc R U . . .
H2B H 0.404225 0.543170 0.422069 0.036 Uiso 1 1 calc R U . . .
C3 C 0.7157(2) 0.6178(2) 0.04334(12) 0.0399(4) Uani 1 1 d . . . . .
H3A H 0.728663 0.506091 0.063313 0.048 Uiso 1 1 calc R U . . .
H3B H 0.764160 0.634425 -0.027466 0.048 Uiso 1 1 calc R U . . .
C4 C 0.5312(2) 0.7163(2) 0.05217(13) 0.0432(4) Uani 1 1 d . . . . .
H4A H 0.514237 0.795296 -0.009380 0.052 Uiso 1 1 calc R U . . .
H4B H 0.475187 0.645470 0.052904 0.052 Uiso 1 1 calc R U . . .
C11 C 0.77677(18) 0.63506(18) 0.21084(11) 0.0287(3) Uani 1 1 d . . . . .
C12 C 0.8127(2) 0.6514(2) 0.10417(12) 0.0338(4) Uani 1 1 d . . . . .
C13 C 0.9443(2) 0.7000(2) 0.05368(14) 0.0445(4) Uani 1 1 d . . . . .
H13 H 0.969772 0.709863 -0.016472 0.053 Uiso 1 1 calc R U . . .
C14 C 1.0377(2) 0.7337(2) 0.10437(15) 0.0497(5) Uani 1 1 d . . . . .
H14 H 1.125090 0.765275 0.068766 0.060 Uiso 1 1 calc R U . . .
C15 C 1.0008(2) 0.7202(2) 0.20821(15) 0.0444(4) Uani 1 1 d . . . . .
H15 H 1.062551 0.743677 0.243067 0.053 Uiso 1 1 calc R U . . .
C16 C 0.8711(2) 0.6715(2) 0.26060(12) 0.0356(4) Uani 1 1 d . . . . .
H16 H 0.846672 0.663114 0.330688 0.043 Uiso 1 1 calc R U . . .
C21 C 0.47951(18) 0.74759(18) 0.24052(11) 0.0275(3) Uani 1 1 d . . . . .
C22 C 0.44467(19) 0.80277(19) 0.14066(12) 0.0327(3) Uani 1 1 d . . . . .
C23 C 0.3205(2) 0.9499(2) 0.11935(14) 0.0414(4) Uani 1 1 d . . . . .
H23 H 0.296026 0.986764 0.053796 0.050 Uiso 1 1 calc R U . . .
C24 C 0.2328(2) 1.0427(2) 0.19250(16) 0.0455(5) Uani 1 1 d . . . . .
H24 H 0.149539 1.139711 0.176419 0.055 Uiso 1 1 calc R U . . .
C25 C 0.2694(2) 0.9904(2) 0.28902(15) 0.0420(4) Uani 1 1 d . . . . .
H25 H 0.211773 1.052515 0.338658 0.050 Uiso 1 1 calc R U . . .
C26 C 0.3924(2) 0.84514(19) 0.31241(12) 0.0338(3) Uani 1 1 d . . . . .
H26 H 0.417632 0.811689 0.377816 0.041 Uiso 1 1 calc R U . . .
C31 C 0.6211(2) 0.44480(18) 0.24199(11) 0.0296(3) Uani 1 1 d . . . . .
C32 C 0.4774(2) 0.4336(2) 0.22940(13) 0.0383(4) Uani 1 1 d . . . . .
H32 H 0.379682 0.520598 0.234128 0.046 Uiso 1 1 calc R U . . .
C33 C 0.4778(3) 0.2941(3) 0.20983(15) 0.0507(5) Uani 1 1 d . . . . .
H33 H 0.380485 0.288380 0.201678 0.061 Uiso 1 1 calc R U . . .
C34 C 0.6212(3) 0.1645(2) 0.20245(16) 0.0553(5) Uani 1 1 d . . . . .
H34 H 0.621269 0.071493 0.188784 0.066 Uiso 1 1 calc R U . . .
C35 C 0.7645(3) 0.1731(2) 0.21538(15) 0.0501(5) Uani 1 1 d . . . . .
H35 H 0.862027 0.085929 0.209818 0.060 Uiso 1 1 calc R U . . .
C36 C 0.7640(2) 0.3111(2) 0.23666(13) 0.0396(4) Uani 1 1 d . . . . .
H36 H 0.860856 0.314355 0.247566 0.048 Uiso 1 1 calc R U . . .
C41 C 0.1324(3) 0.3423(3) 0.42189(18) 0.0592(6) Uani 1 1 d . . . . .
H41 H 0.147355 0.428389 0.374146 0.071 Uiso 1 1 calc R U . . .
C42 C 0.2640(3) 0.2346(3) 0.46555(19) 0.0626(6) Uani 1 1 d . . . . .
H42 H 0.365942 0.246320 0.446790 0.075 Uiso 1 1 calc R U . . .
C43 C 0.2437(3) 0.1093(3) 0.53717(18) 0.0624(6) Uani 1 1 d . . . . .
H43 H 0.330962 0.034563 0.568721 0.075 Uiso 1 1 calc R U . . .
C44 C 0.0920(3) 0.0961(3) 0.56148(17) 0.0643(6) Uani 1 1 d . . . . .
H44 H 0.073508 0.012044 0.609711 0.077 Uiso 1 1 calc R U . . .
C45 C -0.0315(3) 0.2096(3) 0.51312(18) 0.0631(6) Uani 1 1 d . . . . .
H45 H -0.134491 0.200109 0.530518 0.076 Uiso 1 1 calc R U . . .
H1 H 0.728(2) 0.500(2) 0.3903(13) 0.034(5) Uiso 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C2 1.4671(19) . ?
N1 C1 1.4883(18) . ?
N1 H1 0.886(19) . ?
N4 C45 1.318(3) . ?
N4 C41 1.327(3) . ?
C1 C31 1.534(2) . ?
C1 C11 1.544(2) . ?
C1 C21 1.546(2) . ?
C2 C2 1.522(3) 2_666 ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C3 C12 1.504(3) . ?
C3 C4 1.534(2) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C4 C22 1.514(2) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C11 C16 1.390(2) . ?
C11 C12 1.413(2) . ?
C12 C13 1.396(2) . ?
C13 C14 1.376(3) . ?
C13 H13 0.9300 . ?
C14 C15 1.377(3) . ?
C14 H14 0.9300 . ?
C15 C16 1.387(2) . ?
C15 H15 0.9300 . ?
C16 H16 0.9300 . ?
C21 C26 1.394(2) . ?
C21 C22 1.409(2) . ?
C22 C23 1.394(2) . ?
C23 C24 1.381(3) . ?
C23 H23 0.9300 . ?
C24 C25 1.371(3) . ?
C24 H24 0.9300 . ?
C25 C26 1.384(2) . ?
C25 H25 0.9300 . ?
C26 H26 0.9300 . ?
C31 C32 1.388(2) . ?
C31 C36 1.390(2) . ?
C32 C33 1.388(3) . ?
C32 H32 0.9300 . ?
C33 C34 1.374(3) . ?
C33 H33 0.9300 . ?
C34 C35 1.375(3) . ?
C34 H34 0.9300 . ?
C35 C36 1.385(3) . ?
C35 H35 0.9300 . ?
C36 H36 0.9300 . ?
C41 C42 1.364(3) . ?
C41 H41 0.9300 . ?
C42 C43 1.364(3) . ?
C42 H42 0.9300 . ?
C43 C44 1.368(3) . ?
C43 H43 0.9300 . ?
C44 C45 1.364(3) . ?
C44 H44 0.9300 . ?
C45 H45 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 N1 C1 115.90(12) . . ?
C2 N1 H1 109.6(12) . . ?
C1 N1 H1 107.6(12) . . ?
C45 N4 C41 115.8(2) . . ?
N1 C1 C31 108.24(11) . . ?
N1 C1 C11 109.15(12) . . ?
C31 C1 C11 112.27(12) . . ?
N1 C1 C21 109.83(11) . . ?
C31 C1 C21 114.11(12) . . ?
C11 C1 C21 103.10(11) . . ?
N1 C2 C2 110.52(16) . 2_666 ?
N1 C2 H2A 109.5 . . ?
C2 C2 H2A 109.5 2_666 . ?
N1 C2 H2B 109.5 . . ?
C2 C2 H2B 109.5 2_666 . ?
H2A C2 H2B 108.1 . . ?
C12 C3 C4 116.99(14) . . ?
C12 C3 H3A 108.1 . . ?
C4 C3 H3A 108.1 . . ?
C12 C3 H3B 108.1 . . ?
C4 C3 H3B 108.1 . . ?
H3A C3 H3B 107.3 . . ?
C22 C4 C3 119.95(15) . . ?
C22 C4 H4A 107.3 . . ?
C3 C4 H4A 107.3 . . ?
C22 C4 H4B 107.3 . . ?
C3 C4 H4B 107.3 . . ?
H4A C4 H4B 106.9 . . ?
C16 C11 C12 118.78(14) . . ?
C16 C11 C1 120.95(13) . . ?
C12 C11 C1 120.00(14) . . ?
C13 C12 C11 118.26(17) . . ?
C13 C12 C3 118.98(15) . . ?
C11 C12 C3 122.76(15) . . ?
C14 C13 C12 122.13(17) . . ?
C14 C13 H13 118.9 . . ?
C12 C13 H13 118.9 . . ?
C13 C14 C15 119.51(17) . . ?
C13 C14 H14 120.2 . . ?
C15 C14 H14 120.2 . . ?
C14 C15 C16 119.72(18) . . ?
C14 C15 H15 120.1 . . ?
C16 C15 H15 120.1 . . ?
C15 C16 C11 121.58(15) . . ?
C15 C16 H16 119.2 . . ?
C11 C16 H16 119.2 . . ?
C26 C21 C22 118.49(14) . . ?
C26 C21 C1 119.06(13) . . ?
C22 C21 C1 122.00(13) . . ?
C23 C22 C21 118.39(15) . . ?
C23 C22 C4 115.84(15) . . ?
C21 C22 C4 125.76(14) . . ?
C24 C23 C22 122.08(17) . . ?
C24 C23 H23 119.0 . . ?
C22 C23 H23 119.0 . . ?
C25 C24 C23 119.43(17) . . ?
C25 C24 H24 120.3 . . ?
C23 C24 H24 120.3 . . ?
C24 C25 C26 119.83(17) . . ?
C24 C25 H25 120.1 . . ?
C26 C25 H25 120.1 . . ?
C25 C26 C21 121.73(16) . . ?
C25 C26 H26 119.1 . . ?
C21 C26 H26 119.1 . . ?
C32 C31 C36 117.92(15) . . ?
C32 C31 C1 122.61(14) . . ?
C36 C31 C1 119.32(14) . . ?
C33 C32 C31 120.85(17) . . ?
C33 C32 H32 119.6 . . ?
C31 C32 H32 119.6 . . ?
C34 C33 C32 120.32(19) . . ?
C34 C33 H33 119.8 . . ?
C32 C33 H33 119.8 . . ?
C33 C34 C35 119.66(18) . . ?
C33 C34 H34 120.2 . . ?
C35 C34 H34 120.2 . . ?
C34 C35 C36 120.16(19) . . ?
C34 C35 H35 119.9 . . ?
C36 C35 H35 119.9 . . ?
C35 C36 C31 121.05(18) . . ?
C35 C36 H36 119.5 . . ?
C31 C36 H36 119.5 . . ?
N4 C41 C42 123.9(2) . . ?
N4 C41 H41 118.1 . . ?
C42 C41 H41 118.1 . . ?
C43 C42 C41 118.9(2) . . ?
C43 C42 H42 120.5 . . ?
C41 C42 H42 120.5 . . ?
C42 C43 C44 118.4(2) . . ?
C42 C43 H43 120.8 . . ?
C44 C43 H43 120.8 . . ?
C45 C44 C43 118.2(2) . . ?
C45 C44 H44 120.9 . . ?
C43 C44 H44 120.9 . . ?
N4 C45 C44 124.8(2) . . ?
N4 C45 H45 117.6 . . ?
C44 C45 H45 117.6 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C2 N1 C1 C31 -46.00(17) . . . . ?
C2 N1 C1 C11 -168.47(12) . . . . ?
C2 N1 C1 C21 79.18(16) . . . . ?
C1 N1 C2 C2 -164.03(16) . . . 2_666 ?
C12 C3 C4 C22 -18.3(2) . . . . ?
N1 C1 C11 C16 -13.35(19) . . . . ?
C31 C1 C11 C16 -133.37(15) . . . . ?
C21 C1 C11 C16 103.36(15) . . . . ?
N1 C1 C11 C12 172.68(14) . . . . ?
C31 C1 C11 C12 52.67(18) . . . . ?
C21 C1 C11 C12 -70.60(16) . . . . ?
C16 C11 C12 C13 1.5(2) . . . . ?
C1 C11 C12 C13 175.60(15) . . . . ?
C16 C11 C12 C3 -178.81(15) . . . . ?
C1 C11 C12 C3 -4.7(2) . . . . ?
C4 C3 C12 C13 -121.02(18) . . . . ?
C4 C3 C12 C11 59.3(2) . . . . ?
C11 C12 C13 C14 -0.7(3) . . . . ?
C3 C12 C13 C14 179.57(17) . . . . ?
C12 C13 C14 C15 -0.3(3) . . . . ?
C13 C14 C15 C16 0.6(3) . . . . ?
C14 C15 C16 C11 0.2(3) . . . . ?
C12 C11 C16 C15 -1.3(2) . . . . ?
C1 C11 C16 C15 -175.32(15) . . . . ?
N1 C1 C21 C26 9.84(18) . . . . ?
C31 C1 C21 C26 131.57(14) . . . . ?
C11 C1 C21 C26 -106.39(15) . . . . ?
N1 C1 C21 C22 -178.01(14) . . . . ?
C31 C1 C21 C22 -56.28(18) . . . . ?
C11 C1 C21 C22 65.76(17) . . . . ?
C26 C21 C22 C23 -2.3(2) . . . . ?
C1 C21 C22 C23 -174.47(14) . . . . ?
C26 C21 C22 C4 177.47(17) . . . . ?
C1 C21 C22 C4 5.3(2) . . . . ?
C3 C4 C22 C23 144.22(17) . . . . ?
C3 C4 C22 C21 -35.5(3) . . . . ?
C21 C22 C23 C24 0.6(3) . . . . ?
C4 C22 C23 C24 -179.18(18) . . . . ?
C22 C23 C24 C25 0.9(3) . . . . ?
C23 C24 C25 C26 -0.6(3) . . . . ?
C24 C25 C26 C21 -1.1(3) . . . . ?
C22 C21 C26 C25 2.6(2) . . . . ?
C1 C21 C26 C25 175.02(15) . . . . ?
N1 C1 C31 C32 99.70(16) . . . . ?
C11 C1 C31 C32 -139.76(15) . . . . ?
C21 C1 C31 C32 -22.90(19) . . . . ?
N1 C1 C31 C36 -75.57(17) . . . . ?
C11 C1 C31 C36 44.97(18) . . . . ?
C21 C1 C31 C36 161.82(14) . . . . ?
C36 C31 C32 C33 -1.4(2) . . . . ?
C1 C31 C32 C33 -176.76(16) . . . . ?
C31 C32 C33 C34 -0.1(3) . . . . ?
C32 C33 C34 C35 0.5(3) . . . . ?
C33 C34 C35 C36 0.6(3) . . . . ?
C34 C35 C36 C31 -2.2(3) . . . . ?
C32 C31 C36 C35 2.6(3) . . . . ?
C1 C31 C36 C35 178.06(16) . . . . ?
C45 N4 C41 C42 1.4(4) . . . . ?
N4 C41 C42 C43 -1.3(4) . . . . ?
C41 C42 C43 C44 0.7(4) . . . . ?
C42 C43 C44 C45 -0.3(4) . . . . ?
C41 N4 C45 C44 -1.0(4) . . . . ?
C43 C44 C45 N4 0.5(4) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
N1 H1 N4 0.886(19) 2.38(2) 3.255(2) 171.8(16) 1_655 yes
C16 H16 N1 0.93 2.39 2.772(2) 105 . yes
C26 H26 N1 0.93 2.33 2.743(2) 106 . yes

_refine_diff_density_max         0.226
_refine_diff_density_min         -0.185
_refine_diff_density_rms         0.035


_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_ma049
_database_code_depnum_ccdc_archive 'CCDC 2241126'
loop_
_audit_author_name
_audit_author_address
'Eric Hosten'
;Nelson Mandela University
South Africa
;
_audit_update_record             
;
2023-02-10 deposited with the CCDC.	2023-10-20 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        
;
N,N'-Bis(5-phenyl-5-dibenzo[a,d]cycloheptenyl)ethylenediamine
;
_chemical_name_common            ?
_chemical_melting_point          336.35
_chemical_formula_moiety         'C44 H36 N2, 2(C6 H7 N)'
_chemical_formula_sum            'C56 H50 N4'
_chemical_formula_weight         779.00

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'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

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

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.7173(6)
_cell_length_b                   11.2718(8)
_cell_length_c                   12.6826(9)
_cell_angle_alpha                108.163(3)
_cell_angle_beta                 105.764(2)
_cell_angle_gamma                104.337(2)
_cell_volume                     1061.65(13)
_cell_formula_units_Z            1
_cell_measurement_temperature    200(2)
_cell_measurement_reflns_used    9851
_cell_measurement_theta_min      2.55
_cell_measurement_theta_max      28.30

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.218
_exptl_crystal_F_000             414
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.780
_exptl_crystal_size_mid          0.745
_exptl_crystal_size_min          0.450
_exptl_absorpt_coefficient_mu    0.071
_shelx_estimated_absorpt_T_min   0.947
_shelx_estimated_absorpt_T_max   0.969
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_correction_T_min  0.9594
_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            33628
_diffrn_reflns_av_unetI/netI     0.0151
_diffrn_reflns_av_R_equivalents  0.0221
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         1.826
_diffrn_reflns_theta_max         28.375
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             5285
_reflns_number_gt                4470
_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 nitrogen-bound H atoms were located on a difference map and refined freely.

The solvent/guest 2-methylpyridine has positional disorder necessitating the use
of RIGU and SAME.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0519P)²+0.2664P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_extinction_coef       0.034(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         5285
_refine_ls_number_parameters     342
_refine_ls_number_restraints     105
_refine_ls_R_factor_all          0.0474
_refine_ls_R_factor_gt           0.0392
_refine_ls_wR_factor_ref         0.1095
_refine_ls_wR_factor_gt          0.1020
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_restrained_S_all      1.021
_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
N1 N 0.60591(10) 0.15448(8) 0.64177(7) 0.02331(17) Uani 1 1 d . . . . .
C1 C 0.59083(11) 0.20643(9) 0.75964(8) 0.02153(18) Uani 1 1 d . . . . .
C2 C 0.47364(12) 0.02528(9) 0.55259(8) 0.0255(2) Uani 1 1 d . . . . .
H2A H 0.362666 0.036523 0.524591 0.031 Uiso 1 1 calc R U . . .
H2B H 0.460033 -0.040463 0.589215 0.031 Uiso 1 1 calc R U . . .
C3 C 0.57800(13) 0.26095(11) 1.00365(9) 0.0315(2) Uani 1 1 d . . . . .
H3 H 0.510436 0.239748 1.047406 0.038 Uiso 1 1 calc R U . . .
C4 C 0.60627(13) 0.38128(11) 0.99932(9) 0.0313(2) Uani 1 1 d . . . . .
H4 H 0.558748 0.437635 1.041711 0.038 Uiso 1 1 calc R U . . .
C11 C 0.65563(11) 0.13340(9) 0.83577(8) 0.02361(19) Uani 1 1 d . . . . .
C12 C 0.64063(12) 0.15889(10) 0.94780(9) 0.0271(2) Uani 1 1 d . . . . .
C13 C 0.69513(14) 0.08711(11) 1.01370(10) 0.0341(2) Uani 1 1 d . . . . .
H13 H 0.679784 0.100835 1.087358 0.041 Uiso 1 1 calc R U . . .
C14 C 0.77030(14) -0.00269(12) 0.97397(11) 0.0377(3) Uani 1 1 d . . . . .
H14 H 0.807487 -0.049642 1.020106 0.045 Uiso 1 1 calc R U . . .
C15 C 0.79100(14) -0.02371(11) 0.86595(10) 0.0351(2) Uani 1 1 d . . . . .
H15 H 0.845039 -0.083921 0.838698 0.042 Uiso 1 1 calc R U . . .
C16 C 0.73318(12) 0.04276(10) 0.79721(9) 0.0281(2) Uani 1 1 d . . . . .
H16 H 0.746637 0.026269 0.722714 0.034 Uiso 1 1 calc R U . . .
C21 C 0.71007(11) 0.35479(9) 0.82827(8) 0.02351(19) Uani 1 1 d . . . . .
C22 C 0.70283(12) 0.43468(10) 0.93600(9) 0.0275(2) Uani 1 1 d . . . . .
C23 C 0.80010(14) 0.57293(11) 0.99022(10) 0.0347(2) Uani 1 1 d . . . . .
H23 H 0.789118 0.628078 1.059522 0.042 Uiso 1 1 calc R U . . .
C24 C 0.91087(14) 0.63009(11) 0.94505(11) 0.0394(3) Uani 1 1 d . . . . .
H24 H 0.975641 0.723581 0.982769 0.047 Uiso 1 1 calc R U . . .
C25 C 0.92660(14) 0.54963(11) 0.84409(11) 0.0375(3) Uani 1 1 d . . . . .
H25 H 1.006570 0.587335 0.814483 0.045 Uiso 1 1 calc R U . . .
C26 C 0.82609(12) 0.41391(10) 0.78566(9) 0.0294(2) Uani 1 1 d . . . . .
H26 H 0.836623 0.360438 0.715411 0.035 Uiso 1 1 calc R U . . .
C31 C 0.40285(11) 0.19170(9) 0.73832(8) 0.02375(19) Uani 1 1 d . . . . .
C32 C 0.34192(13) 0.28235(10) 0.70444(9) 0.0303(2) Uani 1 1 d . . . . .
H32 H 0.419307 0.357446 0.703256 0.036 Uiso 1 1 calc R U . . .
C33 C 0.16975(14) 0.26510(13) 0.67226(11) 0.0396(3) Uani 1 1 d . . . . .
H33 H 0.130764 0.328511 0.649777 0.048 Uiso 1 1 calc R U . . .
C34 C 0.05493(14) 0.15620(13) 0.67278(12) 0.0427(3) Uani 1 1 d . . . . .
H34 H -0.062729 0.144536 0.651217 0.051 Uiso 1 1 calc R U . . .
C35 C 0.11338(14) 0.06464(13) 0.70502(11) 0.0406(3) Uani 1 1 d . . . . .
H35 H 0.035186 -0.010757 0.705229 0.049 Uiso 1 1 calc R U . . .
C36 C 0.28605(13) 0.08162(11) 0.73730(9) 0.0311(2) Uani 1 1 d . . . . .
H36 H 0.324264 0.017393 0.758803 0.037 Uiso 1 1 calc R U . . .
H1 H 0.6000(16) 0.2160(13) 0.6102(11) 0.033(3) Uiso 1 1 d . . . . .
C41 C 0.6533(4) 0.3280(2) 0.4066(2) 0.0452(6) Uani 0.581(4) 1 d D . P A 1
N4 N 0.5558(16) 0.2995(17) 0.4667(12) 0.0485(14) Uani 0.581(4) 1 d D . P A 1
C42 C 0.4031(5) 0.3116(3) 0.4361(2) 0.0513(7) Uani 0.581(4) 1 d D . P A 1
H42 H 0.332433 0.290401 0.477993 0.062 Uiso 0.581(4) 1 calc R U P A 1
C43 C 0.3421(4) 0.3532(2) 0.3471(2) 0.0532(7) Uani 0.581(4) 1 d D . P A 1
H43 H 0.232831 0.361042 0.328655 0.064 Uiso 0.581(4) 1 calc R U P A 1
C44 C 0.4434(5) 0.3830(4) 0.2862(3) 0.0541(9) Uani 0.581(4) 1 d D . P A 1
H44 H 0.405487 0.412295 0.224588 0.065 Uiso 0.581(4) 1 calc R U P A 1
C45 C 0.5995(6) 0.3701(4) 0.3149(3) 0.0492(9) Uani 0.581(4) 1 d D . P A 1
H45 H 0.670859 0.389641 0.272976 0.059 Uiso 0.581(4) 1 calc R U P A 1
C46 C 0.8230(5) 0.3126(4) 0.4423(4) 0.0708(10) Uani 0.581(4) 1 d D . P A 1
H46A H 0.809743 0.230246 0.455750 0.106 Uiso 0.581(4) 1 calc R U P A 1
H46B H 0.903543 0.389760 0.516275 0.106 Uiso 0.581(4) 1 calc R U P A 1
H46C H 0.867011 0.307693 0.378308 0.106 Uiso 0.581(4) 1 calc R U P A 1
C51 C 0.4768(5) 0.3340(3) 0.3946(3) 0.0487(10) Uani 0.419(4) 1 d D . P A 2
N5 N 0.586(2) 0.301(3) 0.4658(18) 0.052(2) Uani 0.419(4) 1 d D . P A 2
C52 C 0.7371(7) 0.3130(5) 0.4556(4) 0.0615(11) Uani 0.419(4) 1 d D . P A 2
H52 H 0.814028 0.287813 0.505164 0.074 Uiso 0.419(4) 1 calc R U P A 2
C53 C 0.7886(6) 0.3597(4) 0.3782(3) 0.0680(13) Uani 0.419(4) 1 d D . P A 2
H53 H 0.898503 0.368512 0.375350 0.082 Uiso 0.419(4) 1 calc R U P A 2
C54 C 0.6746(8) 0.3934(5) 0.3048(4) 0.0662(15) Uani 0.419(4) 1 d D . P A 2
H54 H 0.704266 0.425746 0.249575 0.079 Uiso 0.419(4) 1 calc R U P A 2
C55 C 0.5198(10) 0.3795(5) 0.3127(5) 0.0584(17) Uani 0.419(4) 1 d D . P A 2
H55 H 0.439773 0.401225 0.261717 0.070 Uiso 0.419(4) 1 calc R U P A 2
C56 C 0.3101(7) 0.3197(4) 0.4068(4) 0.0664(12) Uani 0.419(4) 1 d D . P A 2
H56A H 0.228136 0.316209 0.334504 0.100 Uiso 0.419(4) 1 calc R U P A 2
H56B H 0.324255 0.396573 0.476747 0.100 Uiso 0.419(4) 1 calc R U P A 2
H56C H 0.267245 0.236930 0.417372 0.100 Uiso 0.419(4) 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
N1 C2 1.4705(12) . ?
N1 C1 1.4812(11) . ?
N1 H1 0.907(13) . ?
C1 C11 1.5357(12) . ?
C1 C21 1.5410(12) . ?
C1 C31 1.5435(12) . ?
C2 C2 1.5179(18) 2_656 ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 C4 1.3385(16) . ?
C3 C12 1.4617(15) . ?
C3 H3 0.9500 . ?
C4 C22 1.4607(14) . ?
C4 H4 0.9500 . ?
C11 C16 1.3965(13) . ?
C11 C12 1.4084(13) . ?
C12 C13 1.4054(14) . ?
C13 C14 1.3775(17) . ?
C13 H13 0.9500 . ?
C14 C15 1.3852(17) . ?
C14 H14 0.9500 . ?
C15 C16 1.3896(14) . ?
C15 H15 0.9500 . ?
C16 H16 0.9500 . ?
C21 C26 1.3953(13) . ?
C21 C22 1.4104(13) . ?
C22 C23 1.4075(14) . ?
C23 C24 1.3778(17) . ?
C23 H23 0.9500 . ?
C24 C25 1.3835(17) . ?
C24 H24 0.9500 . ?
C25 C26 1.3906(15) . ?
C25 H25 0.9500 . ?
C26 H26 0.9500 . ?
C31 C32 1.3890(14) . ?
C31 C36 1.3906(14) . ?
C32 C33 1.3892(14) . ?
C32 H32 0.9500 . ?
C33 C34 1.3816(18) . ?
C33 H33 0.9500 . ?
C34 C35 1.3792(18) . ?
C34 H34 0.9500 . ?
C35 C36 1.3941(14) . ?
C35 H35 0.9500 . ?
C36 H36 0.9500 . ?
C41 N4 1.333(10) . ?
C41 C45 1.398(5) . ?
C41 C46 1.495(4) . ?
N4 C42 1.336(12) . ?
C42 C43 1.380(4) . ?
C42 H42 0.9500 . ?
C43 C44 1.370(5) . ?
C43 H43 0.9500 . ?
C44 C45 1.367(5) . ?
C44 H44 0.9500 . ?
C45 H45 0.9500 . ?
C46 H46A 0.9800 . ?
C46 H46B 0.9800 . ?
C46 H46C 0.9800 . ?
C51 N5 1.337(13) . ?
C51 C55 1.389(6) . ?
C51 C56 1.479(7) . ?
N5 C52 1.333(16) . ?
C52 C53 1.374(6) . ?
C52 H52 0.9500 . ?
C53 C54 1.379(7) . ?
C53 H53 0.9500 . ?
C54 C55 1.355(8) . ?
C54 H54 0.9500 . ?
C55 H55 0.9500 . ?
C56 H56A 0.9800 . ?
C56 H56B 0.9800 . ?
C56 H56C 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
C2 N1 C1 116.13(7) . . ?
C2 N1 H1 107.3(8) . . ?
C1 N1 H1 107.3(8) . . ?
N1 C1 C11 110.34(7) . . ?
N1 C1 C21 108.34(7) . . ?
C11 C1 C21 106.12(7) . . ?
N1 C1 C31 108.59(7) . . ?
C11 C1 C31 112.55(7) . . ?
C21 C1 C31 110.81(7) . . ?
N1 C2 C2 109.06(9) . 2_656 ?
N1 C2 H2A 109.9 . . ?
C2 C2 H2A 109.9 2_656 . ?
N1 C2 H2B 109.9 . . ?
C2 C2 H2B 109.9 2_656 . ?
H2A C2 H2B 108.3 . . ?
C4 C3 C12 126.54(9) . . ?
C4 C3 H3 116.7 . . ?
C12 C3 H3 116.7 . . ?
C3 C4 C22 126.56(9) . . ?
C3 C4 H4 116.7 . . ?
C22 C4 H4 116.7 . . ?
C16 C11 C12 118.55(9) . . ?
C16 C11 C1 121.20(8) . . ?
C12 C11 C1 120.24(8) . . ?
C13 C12 C11 119.11(9) . . ?
C13 C12 C3 116.97(9) . . ?
C11 C12 C3 123.87(9) . . ?
C14 C13 C12 121.53(10) . . ?
C14 C13 H13 119.2 . . ?
C12 C13 H13 119.2 . . ?
C13 C14 C15 119.21(10) . . ?
C13 C14 H14 120.4 . . ?
C15 C14 H14 120.4 . . ?
C14 C15 C16 120.38(10) . . ?
C14 C15 H15 119.8 . . ?
C16 C15 H15 119.8 . . ?
C15 C16 C11 121.13(10) . . ?
C15 C16 H16 119.4 . . ?
C11 C16 H16 119.4 . . ?
C26 C21 C22 118.33(9) . . ?
C26 C21 C1 121.37(8) . . ?
C22 C21 C1 120.29(8) . . ?
C23 C22 C21 119.08(9) . . ?
C23 C22 C4 117.11(9) . . ?
C21 C22 C4 123.72(9) . . ?
C24 C23 C22 121.48(10) . . ?
C24 C23 H23 119.3 . . ?
C22 C23 H23 119.3 . . ?
C23 C24 C25 119.18(10) . . ?
C23 C24 H24 120.4 . . ?
C25 C24 H24 120.4 . . ?
C24 C25 C26 120.41(10) . . ?
C24 C25 H25 119.8 . . ?
C26 C25 H25 119.8 . . ?
C25 C26 C21 121.24(10) . . ?
C25 C26 H26 119.4 . . ?
C21 C26 H26 119.4 . . ?
C32 C31 C36 118.10(9) . . ?
C32 C31 C1 119.12(8) . . ?
C36 C31 C1 122.30(9) . . ?
C31 C32 C33 121.14(10) . . ?
C31 C32 H32 119.4 . . ?
C33 C32 H32 119.4 . . ?
C34 C33 C32 120.35(11) . . ?
C34 C33 H33 119.8 . . ?
C32 C33 H33 119.8 . . ?
C35 C34 C33 119.12(10) . . ?
C35 C34 H34 120.4 . . ?
C33 C34 H34 120.4 . . ?
C34 C35 C36 120.68(10) . . ?
C34 C35 H35 119.7 . . ?
C36 C35 H35 119.7 . . ?
C31 C36 C35 120.60(10) . . ?
C31 C36 H36 119.7 . . ?
C35 C36 H36 119.7 . . ?
N4 C41 C45 121.7(5) . . ?
N4 C41 C46 116.5(5) . . ?
C45 C41 C46 121.8(3) . . ?
C41 N4 C42 117.8(6) . . ?
N4 C42 C43 123.7(5) . . ?
N4 C42 H42 118.1 . . ?
C43 C42 H42 118.1 . . ?
C44 C43 C42 118.2(3) . . ?
C44 C43 H43 120.9 . . ?
C42 C43 H43 120.9 . . ?
C45 C44 C43 119.3(3) . . ?
C45 C44 H44 120.4 . . ?
C43 C44 H44 120.4 . . ?
C44 C45 C41 119.4(4) . . ?
C44 C45 H45 120.3 . . ?
C41 C45 H45 120.3 . . ?
C41 C46 H46A 109.5 . . ?
C41 C46 H46B 109.5 . . ?
H46A C46 H46B 109.5 . . ?
C41 C46 H46C 109.5 . . ?
H46A C46 H46C 109.5 . . ?
H46B C46 H46C 109.5 . . ?
N5 C51 C55 120.7(7) . . ?
N5 C51 C56 117.2(7) . . ?
C55 C51 C56 122.1(5) . . ?
C52 N5 C51 117.8(9) . . ?
N5 C52 C53 124.4(7) . . ?
N5 C52 H52 117.8 . . ?
C53 C52 H52 117.8 . . ?
C52 C53 C54 117.4(5) . . ?
C52 C53 H53 121.3 . . ?
C54 C53 H53 121.3 . . ?
C55 C54 C53 119.0(5) . . ?
C55 C54 H54 120.5 . . ?
C53 C54 H54 120.5 . . ?
C54 C55 C51 120.7(6) . . ?
C54 C55 H55 119.7 . . ?
C51 C55 H55 119.7 . . ?
C51 C56 H56A 109.5 . . ?
C51 C56 H56B 109.5 . . ?
H56A C56 H56B 109.5 . . ?
C51 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
C2 N1 C1 C11 78.04(9) . . . . ?
C2 N1 C1 C21 -166.17(7) . . . . ?
C2 N1 C1 C31 -45.75(10) . . . . ?
C1 N1 C2 C2 -169.37(9) . . . 2_656 ?
C12 C3 C4 C22 1.27(17) . . . . ?
N1 C1 C11 C16 6.35(11) . . . . ?
C21 C1 C11 C16 -110.82(9) . . . . ?
C31 C1 C11 C16 127.82(9) . . . . ?
N1 C1 C11 C12 -174.88(8) . . . . ?
C21 C1 C11 C12 67.96(10) . . . . ?
C31 C1 C11 C12 -53.41(11) . . . . ?
C16 C11 C12 C13 -3.53(13) . . . . ?
C1 C11 C12 C13 177.66(8) . . . . ?
C16 C11 C12 C3 173.64(9) . . . . ?
C1 C11 C12 C3 -5.17(14) . . . . ?
C4 C3 C12 C13 140.85(11) . . . . ?
C4 C3 C12 C11 -36.38(16) . . . . ?
C11 C12 C13 C14 3.18(15) . . . . ?
C3 C12 C13 C14 -174.18(10) . . . . ?
C12 C13 C14 C15 -0.68(16) . . . . ?
C13 C14 C15 C16 -1.42(16) . . . . ?
C14 C15 C16 C11 0.99(15) . . . . ?
C12 C11 C16 C15 1.52(14) . . . . ?
C1 C11 C16 C15 -179.69(9) . . . . ?
N1 C1 C21 C26 -8.61(12) . . . . ?
C11 C1 C21 C26 109.89(9) . . . . ?
C31 C1 C21 C26 -127.64(9) . . . . ?
N1 C1 C21 C22 170.79(8) . . . . ?
C11 C1 C21 C22 -70.72(10) . . . . ?
C31 C1 C21 C22 51.76(11) . . . . ?
C26 C21 C22 C23 5.98(14) . . . . ?
C1 C21 C22 C23 -173.44(9) . . . . ?
C26 C21 C22 C4 -170.67(9) . . . . ?
C1 C21 C22 C4 9.91(14) . . . . ?
C3 C4 C22 C23 -144.47(11) . . . . ?
C3 C4 C22 C21 32.25(16) . . . . ?
C21 C22 C23 C24 -4.56(15) . . . . ?
C4 C22 C23 C24 172.32(10) . . . . ?
C22 C23 C24 C25 0.04(17) . . . . ?
C23 C24 C25 C26 2.96(17) . . . . ?
C24 C25 C26 C21 -1.39(17) . . . . ?
C22 C21 C26 C25 -3.12(15) . . . . ?
C1 C21 C26 C25 176.29(9) . . . . ?
N1 C1 C31 C32 -77.10(10) . . . . ?
C11 C1 C31 C32 160.44(8) . . . . ?
C21 C1 C31 C32 41.78(11) . . . . ?
N1 C1 C31 C36 94.80(10) . . . . ?
C11 C1 C31 C36 -27.67(12) . . . . ?
C21 C1 C31 C36 -146.32(9) . . . . ?
C36 C31 C32 C33 1.03(15) . . . . ?
C1 C31 C32 C33 173.26(9) . . . . ?
C31 C32 C33 C34 -0.34(18) . . . . ?
C32 C33 C34 C35 -0.35(19) . . . . ?
C33 C34 C35 C36 0.31(19) . . . . ?
C32 C31 C36 C35 -1.05(15) . . . . ?
C1 C31 C36 C35 -173.03(9) . . . . ?
C34 C35 C36 C31 0.40(18) . . . . ?
C45 C41 N4 C42 0.4(18) . . . . ?
C46 C41 N4 C42 -179.6(9) . . . . ?
C41 N4 C42 C43 -0.7(18) . . . . ?
N4 C42 C43 C44 0.4(10) . . . . ?
C42 C43 C44 C45 0.2(6) . . . . ?
C43 C44 C45 C41 -0.6(7) . . . . ?
N4 C41 C45 C44 0.3(11) . . . . ?
C46 C41 C45 C44 -179.8(4) . . . . ?
C55 C51 N5 C52 0(3) . . . . ?
C56 C51 N5 C52 180.0(14) . . . . ?
C51 N5 C52 C53 1(3) . . . . ?
N5 C52 C53 C54 -1.3(15) . . . . ?
C52 C53 C54 C55 0.3(7) . . . . ?
C53 C54 C55 C51 0.9(8) . . . . ?
N5 C51 C55 C54 -1.2(15) . . . . ?
C56 C51 C55 C54 179.0(4) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
N1 H1 N4 0.907(13) 2.283(16) 3.143(9) 158.2(12) . yes
N1 H1 N5 0.907(13) 2.303(17) 3.154(12) 156.1(13) . yes
C16 H16 N1 0.95 2.40 2.7846(13) 104 . yes
C26 H26 N1 0.95 2.37 2.7488(13) 103 . yes

_refine_diff_density_max         0.297
_refine_diff_density_min         -0.192
_refine_diff_density_rms         0.035


_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_ma222
_database_code_depnum_ccdc_archive 'CCDC 2241129'
loop_
_audit_author_name
_audit_author_address
'Eric Hosten'
;Nelson Mandela University
South Africa
;
_audit_update_record             
;
2023-02-10 deposited with the CCDC.	2023-10-20 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        
;
N,N'-Bis(5-phenyl-10,11-dihydro-5-dibenzo[a,d]cycloheptenyl)ethylenediamine
;
_chemical_name_common            ?
_chemical_melting_point          341.35
_chemical_formula_moiety         '2(C44 H40 N2), 3(C6 H7 N)'
_chemical_formula_sum            'C106 H101 N7'
_chemical_formula_weight         1472.93

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'

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

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

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

_cell_length_a                   9.0013(3)
_cell_length_b                   26.7346(9)
_cell_length_c                   9.0416(3)
_cell_angle_alpha                90
_cell_angle_beta                 114.066(2)
_cell_angle_gamma                90
_cell_volume                     1986.70(12)
_cell_formula_units_Z            1
_cell_measurement_temperature    200(2)
_cell_measurement_reflns_used    9833
_cell_measurement_theta_min      2.48
_cell_measurement_theta_max      28.15

_exptl_crystal_description       platelets
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.231
_exptl_crystal_F_000             786
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.983
_exptl_crystal_size_mid          0.783
_exptl_crystal_size_min          0.061
_exptl_absorpt_coefficient_mu    0.071
_shelx_estimated_absorpt_T_min   0.933
_shelx_estimated_absorpt_T_max   0.996
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_correction_T_min  0.9478
_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            47566
_diffrn_reflns_av_unetI/netI     0.0157
_diffrn_reflns_av_R_equivalents  0.0244
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -35
_diffrn_reflns_limit_k_max       35
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         2.478
_diffrn_reflns_theta_max         28.319
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             4910
_reflns_number_gt                3894
_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 nitrogen-bound H atoms were located on a difference map and refined freely.

The solvent/guest occurs in two positions and both are disordered around
inversion points.  This necessitated the use of RIGU and SAME and the pyridine
rings were 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.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0595P)²+0.9761P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4910
_refine_ls_number_parameters     318
_refine_ls_number_restraints     105
_refine_ls_R_factor_all          0.0658
_refine_ls_R_factor_gt           0.0499
_refine_ls_wR_factor_ref         0.1362
_refine_ls_wR_factor_gt          0.1238
_refine_ls_goodness_of_fit_ref   1.019
_refine_ls_restrained_S_all      1.014
_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
N1 N 0.58605(14) 0.43924(4) 0.46813(14) 0.0245(2) Uani 1 1 d . . . . .
C1 C 0.56065(15) 0.38473(4) 0.48239(15) 0.0223(3) Uani 1 1 d . . . . .
C2 C 0.61592(19) 0.27507(5) 0.55965(19) 0.0357(3) Uani 1 1 d . . . . .
H2A H 0.627302 0.289387 0.664719 0.043 Uiso 1 1 calc R U . . .
H2B H 0.656028 0.240175 0.579830 0.043 Uiso 1 1 calc R U . . .
C3 C 0.4349(2) 0.27412(6) 0.4459(2) 0.0437(4) Uani 1 1 d . . . . .
H3A H 0.414826 0.242385 0.384325 0.052 Uiso 1 1 calc R U . . .
H3B H 0.373484 0.272116 0.514980 0.052 Uiso 1 1 calc R U . . .
C4 C 0.48765(17) 0.47315(5) 0.51977(17) 0.0271(3) Uani 1 1 d . . . . .
H4A H 0.519718 0.469691 0.637832 0.032 Uiso 1 1 calc R U . . .
H4B H 0.371224 0.464129 0.463711 0.032 Uiso 1 1 calc R U . . .
C11 C 0.70136(16) 0.35597(5) 0.46421(15) 0.0255(3) Uani 1 1 d . . . . .
C12 C 0.72285(17) 0.30422(5) 0.49946(17) 0.0315(3) Uani 1 1 d . . . . .
C13 C 0.8472(2) 0.27925(6) 0.4749(2) 0.0429(4) Uani 1 1 d . . . . .
H13 H 0.863723 0.244648 0.500221 0.052 Uiso 1 1 calc R U . . .
C14 C 0.9467(2) 0.30326(7) 0.4151(2) 0.0456(4) Uani 1 1 d . . . . .
H14 H 1.031022 0.285385 0.400568 0.055 Uiso 1 1 calc R U . . .
C15 C 0.92309(18) 0.35339(7) 0.37650(19) 0.0397(4) Uani 1 1 d . . . . .
H15 H 0.990220 0.370079 0.333901 0.048 Uiso 1 1 calc R U . . .
C16 C 0.80016(16) 0.37958(6) 0.40018(17) 0.0308(3) Uani 1 1 d . . . . .
H16 H 0.783666 0.414002 0.372209 0.037 Uiso 1 1 calc R U . . .
C21 C 0.40675(15) 0.36621(5) 0.33855(16) 0.0235(3) Uani 1 1 d . . . . .
C22 C 0.35772(17) 0.31559(5) 0.32356(17) 0.0284(3) Uani 1 1 d . . . . .
C23 C 0.22392(18) 0.30101(6) 0.18388(19) 0.0340(3) Uani 1 1 d . . . . .
H23 H 0.190315 0.267019 0.172872 0.041 Uiso 1 1 calc R U . . .
C24 C 0.13896(18) 0.33412(6) 0.06154(19) 0.0373(3) Uani 1 1 d . . . . .
H24 H 0.048182 0.323079 -0.031568 0.045 Uiso 1 1 calc R U . . .
C25 C 0.18747(18) 0.38347(6) 0.07611(18) 0.0359(3) Uani 1 1 d . . . . .
H25 H 0.129904 0.406757 -0.006945 0.043 Uiso 1 1 calc R U . . .
C26 C 0.32091(16) 0.39902(5) 0.21276(16) 0.0282(3) Uani 1 1 d . . . . .
H26 H 0.354572 0.432954 0.220661 0.034 Uiso 1 1 calc R U . . .
C31 C 0.55480(16) 0.37513(5) 0.64753(16) 0.0251(3) Uani 1 1 d . . . . .
C32 C 0.41014(18) 0.36621(5) 0.66381(18) 0.0311(3) Uani 1 1 d . . . . .
H32 H 0.310698 0.364511 0.570114 0.037 Uiso 1 1 calc R U . . .
C33 C 0.4100(2) 0.35973(6) 0.8168(2) 0.0415(4) Uani 1 1 d . . . . .
H33 H 0.310415 0.353449 0.826422 0.050 Uiso 1 1 calc R U . . .
C34 C 0.5526(2) 0.36236(6) 0.9538(2) 0.0467(4) Uani 1 1 d . . . . .
H34 H 0.552047 0.357404 1.057636 0.056 Uiso 1 1 calc R U . . .
C35 C 0.6969(2) 0.37229(7) 0.9392(2) 0.0459(4) Uani 1 1 d . . . . .
H35 H 0.795608 0.374528 1.033509 0.055 Uiso 1 1 calc R U . . .
C36 C 0.69808(19) 0.37900(6) 0.78731(18) 0.0344(3) Uani 1 1 d . . . . .
H36 H 0.797526 0.386296 0.778669 0.041 Uiso 1 1 calc R U . . .
H1 H 0.693(2) 0.4455(7) 0.532(2) 0.042(5) Uiso 1 1 d . . . . .
C41 C 1.27789(19) 0.49868(8) 0.9079(2) 0.0338(6) Uani 0.5 1 d DG . P A -1
C42 C 1.2377(2) 0.47595(9) 0.7582(3) 0.0430(8) Uani 0.5 1 d DG . P A -1
H42 H 1.320488 0.468110 0.722275 0.052 Uiso 0.5 1 calc R U P A -1
C43 C 1.0763(3) 0.46468(10) 0.6611(2) 0.0510(11) Uani 0.5 1 d DG . P A -1
H43 H 1.048776 0.449140 0.558772 0.061 Uiso 0.5 1 calc R U P A -1
N4 N 0.9551(2) 0.47614(9) 0.7136(3) 0.0480(7) Uani 0.5 1 d DG . P A -1
C44 C 0.9953(2) 0.49887(9) 0.8633(3) 0.0483(8) Uani 0.5 1 d DG . P A -1
H44 H 0.912480 0.506710 0.899181 0.058 Uiso 0.5 1 calc R U P A -1
C45 C 1.1567(2) 0.51014(8) 0.9604(2) 0.0428(7) Uani 0.5 1 d DG . P A -1
H45 H 1.184191 0.525680 1.062686 0.051 Uiso 0.5 1 calc R U P A -1
C46 C 1.4561(4) 0.50858(15) 1.0120(5) 0.0481(8) Uani 0.5 1 d D . P A -1
H46A H 1.513375 0.476696 1.047337 0.072 Uiso 0.5 1 calc R U P A -1
H46B H 1.466001 0.528257 1.107035 0.072 Uiso 0.5 1 calc R U P A -1
H46C H 1.504101 0.527205 0.948955 0.072 Uiso 0.5 1 calc R U P A -1
C51 C 0.0033(8) 0.5012(3) 0.5415(5) 0.0527(19) Uani 0.25 1 d DG . P B -2
C52 C -0.1064(8) 0.5372(2) 0.4486(6) 0.0502(18) Uani 0.25 1 d DG . P B -2
H52 H -0.156471 0.559052 0.497521 0.060 Uiso 0.25 1 calc R U P B -2
C53 C -0.1428(7) 0.5413(2) 0.2842(6) 0.061(3) Uani 0.25 1 d DG . P B -2
H53 H -0.217723 0.565913 0.220727 0.073 Uiso 0.25 1 calc R U P B -2
N5 N -0.0695(8) 0.5093(3) 0.2126(5) 0.067(2) Uani 0.25 1 d DG . P B -2
C54 C 0.0402(7) 0.4733(2) 0.3055(7) 0.071(2) Uani 0.25 1 d DG . P B -2
H54 H 0.090235 0.451410 0.256616 0.085 Uiso 0.25 1 calc R U P B -2
C55 C 0.0765(7) 0.4692(2) 0.4699(7) 0.0544(19) Uani 0.25 1 d DG . P B -2
H55 H 0.151489 0.444549 0.533409 0.065 Uiso 0.25 1 calc R U P B -2
C56 C 0.0405(16) 0.4925(7) 0.7149(11) 0.111(6) Uani 0.25 1 d D . P B -2
H56A H 0.076303 0.523877 0.774915 0.166 Uiso 0.25 1 calc R U P B -2
H56B H 0.127178 0.467463 0.758626 0.166 Uiso 0.25 1 calc R U P B -2
H56C H -0.057255 0.480352 0.725808 0.166 Uiso 0.25 1 calc R U P B -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
N1 C4 1.4703(16) . ?
N1 C1 1.4890(15) . ?
N1 H1 0.910(19) . ?
C1 C31 1.5369(18) . ?
C1 C21 1.5447(17) . ?
C1 C11 1.5468(17) . ?
C2 C12 1.502(2) . ?
C2 C3 1.532(2) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 C22 1.519(2) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 C4 1.517(2) 3_666 ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C11 C16 1.394(2) . ?
C11 C12 1.4153(19) . ?
C12 C13 1.396(2) . ?
C13 C14 1.380(3) . ?
C13 H13 0.9500 . ?
C14 C15 1.379(3) . ?
C14 H14 0.9500 . ?
C15 C16 1.398(2) . ?
C15 H15 0.9500 . ?
C16 H16 0.9500 . ?
C21 C26 1.3940(18) . ?
C21 C22 1.4127(18) . ?
C22 C23 1.399(2) . ?
C23 C24 1.379(2) . ?
C23 H23 0.9500 . ?
C24 C25 1.379(2) . ?
C24 H24 0.9500 . ?
C25 C26 1.390(2) . ?
C25 H25 0.9500 . ?
C26 H26 0.9500 . ?
C31 C32 1.389(2) . ?
C31 C36 1.394(2) . ?
C32 C33 1.395(2) . ?
C32 H32 0.9500 . ?
C33 C34 1.375(3) . ?
C33 H33 0.9500 . ?
C34 C35 1.384(3) . ?
C34 H34 0.9500 . ?
C35 C36 1.389(2) . ?
C35 H35 0.9500 . ?
C36 H36 0.9500 . ?
C41 C42 1.3900 . ?
C41 C45 1.3900 . ?
C41 C46 1.516(4) . ?
C42 C43 1.3900 . ?
C42 H42 0.9500 . ?
C43 N4 1.3900 . ?
C43 H43 0.9500 . ?
N4 C44 1.3900 . ?
C44 C45 1.3900 . ?
C44 H44 0.9500 . ?
C45 H45 0.9500 . ?
C46 H46A 0.9800 . ?
C46 H46B 0.9800 . ?
C46 H46C 0.9800 . ?
C51 C52 1.3900 . ?
C51 C55 1.3900 . ?
C51 C56 1.482(10) . ?
C52 C53 1.3900 . ?
C52 H52 0.9500 . ?
C53 N5 1.3900 . ?
C53 H53 0.9500 . ?
N5 C54 1.3900 . ?
C54 C55 1.3900 . ?
C54 H54 0.9500 . ?
C55 H55 0.9500 . ?
C56 H56A 0.9800 . ?
C56 H56B 0.9800 . ?
C56 H56C 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
C4 N1 C1 116.25(10) . . ?
C4 N1 H1 107.6(11) . . ?
C1 N1 H1 106.6(11) . . ?
N1 C1 C31 108.36(10) . . ?
N1 C1 C21 110.95(10) . . ?
C31 C1 C21 112.96(10) . . ?
N1 C1 C11 108.42(10) . . ?
C31 C1 C11 111.97(10) . . ?
C21 C1 C11 104.08(10) . . ?
C12 C2 C3 115.38(13) . . ?
C12 C2 H2A 108.4 . . ?
C3 C2 H2A 108.4 . . ?
C12 C2 H2B 108.4 . . ?
C3 C2 H2B 108.4 . . ?
H2A C2 H2B 107.5 . . ?
C22 C3 C2 121.46(13) . . ?
C22 C3 H3A 107.0 . . ?
C2 C3 H3A 107.0 . . ?
C22 C3 H3B 107.0 . . ?
C2 C3 H3B 107.0 . . ?
H3A C3 H3B 106.7 . . ?
N1 C4 C4 110.08(14) . 3_666 ?
N1 C4 H4A 109.6 . . ?
C4 C4 H4A 109.6 3_666 . ?
N1 C4 H4B 109.6 . . ?
C4 C4 H4B 109.6 3_666 . ?
H4A C4 H4B 108.2 . . ?
C16 C11 C12 118.96(12) . . ?
C16 C11 C1 120.51(12) . . ?
C12 C11 C1 120.31(12) . . ?
C13 C12 C11 118.45(15) . . ?
C13 C12 C2 118.88(13) . . ?
C11 C12 C2 122.66(12) . . ?
C14 C13 C12 122.06(15) . . ?
C14 C13 H13 119.0 . . ?
C12 C13 H13 119.0 . . ?
C15 C14 C13 119.56(14) . . ?
C15 C14 H14 120.2 . . ?
C13 C14 H14 120.2 . . ?
C14 C15 C16 119.87(16) . . ?
C14 C15 H15 120.1 . . ?
C16 C15 H15 120.1 . . ?
C11 C16 C15 121.04(14) . . ?
C11 C16 H16 119.5 . . ?
C15 C16 H16 119.5 . . ?
C26 C21 C22 118.48(12) . . ?
C26 C21 C1 119.58(11) . . ?
C22 C21 C1 121.71(11) . . ?
C23 C22 C21 118.29(13) . . ?
C23 C22 C3 115.05(13) . . ?
C21 C22 C3 126.66(13) . . ?
C24 C23 C22 122.47(14) . . ?
C24 C23 H23 118.8 . . ?
C22 C23 H23 118.8 . . ?
C25 C24 C23 119.15(14) . . ?
C25 C24 H24 120.4 . . ?
C23 C24 H24 120.4 . . ?
C24 C25 C26 119.74(14) . . ?
C24 C25 H25 120.1 . . ?
C26 C25 H25 120.1 . . ?
C25 C26 C21 121.86(13) . . ?
C25 C26 H26 119.1 . . ?
C21 C26 H26 119.1 . . ?
C32 C31 C36 118.52(13) . . ?
C32 C31 C1 122.44(12) . . ?
C36 C31 C1 118.88(12) . . ?
C31 C32 C33 120.43(15) . . ?
C31 C32 H32 119.8 . . ?
C33 C32 H32 119.8 . . ?
C34 C33 C32 120.60(16) . . ?
C34 C33 H33 119.7 . . ?
C32 C33 H33 119.7 . . ?
C33 C34 C35 119.44(15) . . ?
C33 C34 H34 120.3 . . ?
C35 C34 H34 120.3 . . ?
C34 C35 C36 120.34(16) . . ?
C34 C35 H35 119.8 . . ?
C36 C35 H35 119.8 . . ?
C35 C36 C31 120.63(15) . . ?
C35 C36 H36 119.7 . . ?
C31 C36 H36 119.7 . . ?
C42 C41 C45 120.0 . . ?
C42 C41 C46 118.08(19) . . ?
C45 C41 C46 121.89(19) . . ?
C43 C42 C41 120.0 . . ?
C43 C42 H42 120.0 . . ?
C41 C42 H42 120.0 . . ?
C42 C43 N4 120.0 . . ?
C42 C43 H43 120.0 . . ?
N4 C43 H43 120.0 . . ?
C43 N4 C44 120.0 . . ?
C45 C44 N4 120.0 . . ?
C45 C44 H44 120.0 . . ?
N4 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 . . ?
C52 C51 C55 120.0 . . ?
C52 C51 C56 123.1(9) . . ?
C55 C51 C56 116.8(9) . . ?
C53 C52 C51 120.0 . . ?
C53 C52 H52 120.0 . . ?
C51 C52 H52 120.0 . . ?
C52 C53 N5 120.0 . . ?
C52 C53 H53 120.0 . . ?
N5 C53 H53 120.0 . . ?
C54 N5 C53 120.0 . . ?
C55 C54 N5 120.0 . . ?
C55 C54 H54 120.0 . . ?
N5 C54 H54 120.0 . . ?
C54 C55 C51 120.0 . . ?
C54 C55 H55 120.0 . . ?
C51 C55 H55 120.0 . . ?
C51 C56 H56A 109.5 . . ?
C51 C56 H56B 109.5 . . ?
H56A C56 H56B 109.5 . . ?
C51 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
C4 N1 C1 C31 -44.36(14) . . . . ?
C4 N1 C1 C21 80.19(14) . . . . ?
C4 N1 C1 C11 -166.10(11) . . . . ?
C12 C2 C3 C22 -25.5(2) . . . . ?
C1 N1 C4 C4 -173.49(13) . . . 3_666 ?
N1 C1 C11 C16 -15.95(16) . . . . ?
C31 C1 C11 C16 -135.45(12) . . . . ?
C21 C1 C11 C16 102.22(13) . . . . ?
N1 C1 C11 C12 169.44(11) . . . . ?
C31 C1 C11 C12 49.94(16) . . . . ?
C21 C1 C11 C12 -72.40(14) . . . . ?
C16 C11 C12 C13 2.6(2) . . . . ?
C1 C11 C12 C13 177.34(12) . . . . ?
C16 C11 C12 C2 -176.42(13) . . . . ?
C1 C11 C12 C2 -1.7(2) . . . . ?
C3 C2 C12 C13 -118.74(16) . . . . ?
C3 C2 C12 C11 60.33(19) . . . . ?
C11 C12 C13 C14 -1.2(2) . . . . ?
C2 C12 C13 C14 177.93(15) . . . . ?
C12 C13 C14 C15 -0.6(3) . . . . ?
C13 C14 C15 C16 0.8(2) . . . . ?
C12 C11 C16 C15 -2.5(2) . . . . ?
C1 C11 C16 C15 -177.15(12) . . . . ?
C14 C15 C16 C11 0.7(2) . . . . ?
N1 C1 C21 C26 4.75(16) . . . . ?
C31 C1 C21 C26 126.65(12) . . . . ?
C11 C1 C21 C26 -111.67(13) . . . . ?
N1 C1 C21 C22 179.24(11) . . . . ?
C31 C1 C21 C22 -58.86(15) . . . . ?
C11 C1 C21 C22 62.82(15) . . . . ?
C26 C21 C22 C23 -0.80(19) . . . . ?
C1 C21 C22 C23 -175.34(12) . . . . ?
C26 C21 C22 C3 179.82(15) . . . . ?
C1 C21 C22 C3 5.3(2) . . . . ?
C2 C3 C22 C23 151.36(15) . . . . ?
C2 C3 C22 C21 -29.2(2) . . . . ?
C21 C22 C23 C24 -0.1(2) . . . . ?
C3 C22 C23 C24 179.37(15) . . . . ?
C22 C23 C24 C25 0.4(2) . . . . ?
C23 C24 C25 C26 0.3(2) . . . . ?
C24 C25 C26 C21 -1.2(2) . . . . ?
C22 C21 C26 C25 1.4(2) . . . . ?
C1 C21 C26 C25 176.11(12) . . . . ?
N1 C1 C31 C32 103.86(13) . . . . ?
C21 C1 C31 C32 -19.49(16) . . . . ?
C11 C1 C31 C32 -136.61(12) . . . . ?
N1 C1 C31 C36 -71.46(14) . . . . ?
C21 C1 C31 C36 165.20(11) . . . . ?
C11 C1 C31 C36 48.08(15) . . . . ?
C36 C31 C32 C33 -2.0(2) . . . . ?
C1 C31 C32 C33 -177.34(12) . . . . ?
C31 C32 C33 C34 0.4(2) . . . . ?
C32 C33 C34 C35 1.0(2) . . . . ?
C33 C34 C35 C36 -0.7(3) . . . . ?
C34 C35 C36 C31 -0.9(2) . . . . ?
C32 C31 C36 C35 2.3(2) . . . . ?
C1 C31 C36 C35 177.78(13) . . . . ?
C45 C41 C42 C43 0.0 . . . . ?
C46 C41 C42 C43 177.9(2) . . . . ?
C41 C42 C43 N4 0.0 . . . . ?
C42 C43 N4 C44 0.0 . . . . ?
C43 N4 C44 C45 0.0 . . . . ?
N4 C44 C45 C41 0.0 . . . . ?
C42 C41 C45 C44 0.0 . . . . ?
C46 C41 C45 C44 -177.8(3) . . . . ?
C55 C51 C52 C53 0.0 . . . . ?
C56 C51 C52 C53 -176.1(10) . . . . ?
C51 C52 C53 N5 0.0 . . . . ?
C52 C53 N5 C54 0.0 . . . . ?
C53 N5 C54 C55 0.0 . . . . ?
N5 C54 C55 C51 0.0 . . . . ?
C52 C51 C55 C54 0.0 . . . . ?
C56 C51 C55 C54 176.4(9) . . . . ?

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
N1 H1 N4 0.910(19) 2.407(19) 3.3046(19) 169.2(16) . yes
C16 H16 N1 0.95 2.37 2.7573(17) 104 . yes
C26 H26 N1 0.95 2.36 2.7730(18) 106 . yes

_refine_diff_density_max         0.384
_refine_diff_density_min         -0.399
_refine_diff_density_rms         0.042


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: 40methylpyridine'
####################################################################### 
# 
# 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_ma156
_database_code_depnum_ccdc_archive 'CCDC 2241127'
loop_
_audit_author_name
_audit_author_address
'Eric Hosten'
;Nelson Mandela University
South Africa
;
_audit_update_record             
;
2023-02-10 deposited with the CCDC.	2023-10-20 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        
;
N,N'-Bis(5-phenyl-5-dibenzo[a,d]cycloheptenyl)ethylenediamine
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C44 H36 N2, 2(C6 H7 N)'
_chemical_formula_sum            'C56 H50 N4'
_chemical_formula_weight         779.00

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'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

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

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.9471(10)
_cell_length_b                   9.9740(11)
_cell_length_c                   13.4375(14)
_cell_angle_alpha                73.488(4)
_cell_angle_beta                 75.543(4)
_cell_angle_gamma                74.301(4)
_cell_volume                     1087.2(2)
_cell_formula_units_Z            1
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    9295
_cell_measurement_theta_min      2.39
_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    1.190
_exptl_crystal_F_000             414
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.781
_exptl_crystal_size_mid          0.563
_exptl_crystal_size_min          0.461
_exptl_absorpt_coefficient_mu    0.069
_shelx_estimated_absorpt_T_min   0.948
_shelx_estimated_absorpt_T_max   0.969
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_correction_T_min  0.9582
_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            39159
_diffrn_reflns_av_unetI/netI     0.0104
_diffrn_reflns_av_R_equivalents  0.0152
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.181
_diffrn_reflns_theta_max         28.320
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             5369
_reflns_number_gt                4428
_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 nitrogen-bound H atoms were located on a difference map and refined freely.

One of the host phenyl groups and the solvent/guest 4-methylpyridine has
positional disorder necessitating the use of RIGU SADI, ISOR and SAME. The
disordered phenyl and pyridine rings were was forced into a regular hexagon with
bond lengths 1.39 Å (AFIX 66 in the SHELXL program (Sheldrick, 2015)).

A number of reflections with large differences between their observed and
calculated intensities were 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)+(0.0933P)²+0.3437P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5369
_refine_ls_number_parameters     346
_refine_ls_number_restraints     262
_refine_ls_R_factor_all          0.0715
_refine_ls_R_factor_gt           0.0604
_refine_ls_wR_factor_ref         0.1859
_refine_ls_wR_factor_gt          0.1718
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_restrained_S_all      1.032
_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
N1 N 0.42677(14) 0.88012(13) 0.62771(8) 0.0365(3) Uani 1 1 d . . . . .
C1 C 0.40957(15) 0.86859(14) 0.74213(10) 0.0360(3) Uani 1 1 d D . . . .
C2 C 0.51127(17) 0.98933(15) 0.55622(10) 0.0386(3) Uani 1 1 d . . . . .
H2A H 0.622945 0.958973 0.559191 0.046 Uiso 1 1 calc R U . . .
H2B H 0.470828 1.079019 0.578270 0.046 Uiso 1 1 calc R U . . .
C3 C 0.3739(2) 0.7704(2) 0.97749(12) 0.0612(5) Uani 1 1 d . . . . .
H3 H 0.425157 0.719397 1.033546 0.073 Uiso 1 1 calc R U . . .
C4 C 0.3366(2) 0.9119(3) 0.96234(13) 0.0631(5) Uani 1 1 d . . . . .
H4 H 0.364629 0.950817 1.008490 0.076 Uiso 1 1 calc R U . . .
C11 C 0.34772(15) 0.73295(15) 0.80488(11) 0.0404(3) Uani 1 1 d . . . . .
C12 C 0.34241(18) 0.68777(19) 0.91506(12) 0.0509(4) Uani 1 1 d . . . . .
C13 C 0.2974(2) 0.5572(2) 0.96902(15) 0.0687(6) Uani 1 1 d . . . . .
H13 H 0.298789 0.524244 1.040917 0.082 Uiso 1 1 calc R U . . .
C14 C 0.2519(3) 0.4775(2) 0.91916(19) 0.0750(6) Uani 1 1 d . . . . .
H14 H 0.222449 0.391803 0.956760 0.090 Uiso 1 1 calc R U . . .
C15 C 0.2499(2) 0.52498(19) 0.81293(18) 0.0644(5) Uani 1 1 d . . . . .
H15 H 0.216157 0.472643 0.778761 0.077 Uiso 1 1 calc R U . . .
C16 C 0.29836(18) 0.65165(16) 0.75608(13) 0.0480(4) Uani 1 1 d . . . . .
H16 H 0.297522 0.682100 0.684034 0.058 Uiso 1 1 calc R U . . .
C21 C 0.28076(17) 0.99271(15) 0.77600(11) 0.0405(3) Uani 1 1 d . . . . .
C22 C 0.2550(2) 1.01296(19) 0.87916(13) 0.0518(4) Uani 1 1 d . . . . .
C23 C 0.1393(3) 1.1297(2) 0.90632(17) 0.0688(5) Uani 1 1 d . . . . .
H23 H 0.125736 1.146660 0.972909 0.083 Uiso 1 1 calc R U . . .
C24 C 0.0452(3) 1.2199(2) 0.8370(2) 0.0743(6) Uani 1 1 d . . . . .
H24 H -0.031779 1.296139 0.856965 0.089 Uiso 1 1 calc R U . . .
C25 C 0.0658(2) 1.19619(19) 0.73724(17) 0.0634(5) Uani 1 1 d . . . . .
H25 H 0.001718 1.255830 0.690215 0.076 Uiso 1 1 calc R U . . .
C26 C 0.18216(19) 1.08358(16) 0.70767(13) 0.0476(3) Uani 1 1 d . . . . .
H26 H 0.194769 1.068237 0.640677 0.057 Uiso 1 1 calc R U . . .
H1 H 0.482(2) 0.797(2) 0.6140(16) 0.053(5) Uiso 1 1 d . . . . .
C31 C 0.5779(5) 0.8517(6) 0.7659(6) 0.0333(8) Uani 0.66(3) 1 d DG . P A 1
C32 C 0.6235(6) 0.9695(6) 0.7754(6) 0.0405(10) Uani 0.66(3) 1 d G . P A 1
H32 H 0.552185 1.057295 0.771755 0.049 Uiso 0.66(3) 1 calc R U P A 1
C33 C 0.7755(7) 0.9560(7) 0.7903(5) 0.0500(12) Uani 0.66(3) 1 d G . P A 1
H33 H 0.806022 1.034817 0.796698 0.060 Uiso 0.66(3) 1 calc R U P A 1
C34 C 0.8821(5) 0.8248(8) 0.7958(5) 0.0554(12) Uani 0.66(3) 1 d G . P A 1
H34 H 0.983833 0.815804 0.805775 0.066 Uiso 0.66(3) 1 calc R U P A 1
C35 C 0.8365(6) 0.7071(7) 0.7863(5) 0.0545(10) Uani 0.66(3) 1 d G . P A 1
H35 H 0.907808 0.619267 0.789907 0.065 Uiso 0.66(3) 1 calc R U P A 1
C36 C 0.6844(6) 0.7205(6) 0.7713(6) 0.0433(9) Uani 0.66(3) 1 d G . P A 1
H36 H 0.653972 0.641741 0.764962 0.052 Uiso 0.66(3) 1 calc R U P A 1
C41 C 0.5650(16) 0.882(3) 0.7653(13) 0.048(3) Uani 0.34(3) 1 d DG . P A 2
C42 C 0.6786(15) 0.755(3) 0.7781(13) 0.059(3) Uani 0.34(3) 1 d G . P A 2
H42 H 0.655406 0.670080 0.776579 0.071 Uiso 0.34(3) 1 calc R U P A 2
C43 C 0.8267(14) 0.755(3) 0.7933(11) 0.068(4) Uani 0.34(3) 1 d G . P A 2
H43 H 0.902733 0.669677 0.801878 0.081 Uiso 0.34(3) 1 calc R U P A 2
C44 C 0.8614(17) 0.881(4) 0.7956(10) 0.079(5) Uani 0.34(3) 1 d G . P A 2
H44 H 0.960500 0.881109 0.805737 0.095 Uiso 0.34(3) 1 calc R U P A 2
C45 C 0.748(2) 1.008(3) 0.7828(12) 0.077(4) Uani 0.34(3) 1 d G . P A 2
H45 H 0.770941 1.092946 0.784298 0.093 Uiso 0.34(3) 1 calc R U P A 2
C46 C 0.5996(19) 1.008(3) 0.7676(13) 0.063(3) Uani 0.34(3) 1 d G . P A 2
H46 H 0.523612 1.093352 0.758998 0.075 Uiso 0.34(3) 1 calc R U P A 2
N5 N 0.6393(5) 0.5684(4) 0.5692(4) 0.100(3) Uani 0.600(10) 1 d DG U P B 3
C51 C 0.5900(5) 0.4393(5) 0.6071(5) 0.098(2) Uani 0.600(10) 1 d DG U P B 3
H51 H 0.493761 0.434868 0.653027 0.117 Uiso 0.600(10) 1 calc R U P B 3
C52 C 0.6847(5) 0.3169(4) 0.5762(5) 0.0811(15) Uani 0.600(10) 1 d DG U P B 3
H52 H 0.651765 0.230569 0.601580 0.097 Uiso 0.600(10) 1 calc R U P B 3
C53 C 0.8286(5) 0.3235(4) 0.5075(3) 0.0657(14) Uani 0.600(10) 1 d DG U P B 3
C54 C 0.8778(6) 0.4526(5) 0.4697(5) 0.096(2) Uani 0.600(10) 1 d DG U P B 3
H54 H 0.974108 0.457027 0.423698 0.115 Uiso 0.600(10) 1 calc R U P B 3
C55 C 0.7832(6) 0.5750(4) 0.5005(5) 0.101(2) Uani 0.600(10) 1 d DG U P B 3
H55 H 0.816107 0.661327 0.475143 0.121 Uiso 0.600(10) 1 calc R U P B 3
C56 C 0.9329(15) 0.1865(10) 0.4798(11) 0.113(4) Uani 0.600(10) 1 d D U P B 3
H56A H 1.027639 0.207165 0.432021 0.169 Uiso 0.600(10) 1 calc R U P B 3
H56B H 0.959764 0.119012 0.543013 0.169 Uiso 0.600(10) 1 calc R U P B 3
H56C H 0.877101 0.146542 0.446855 0.169 Uiso 0.600(10) 1 calc R U P B 3
N6 N 0.6280(6) 0.5833(5) 0.5707(4) 0.066(2) Uani 0.400(10) 1 d DG U P B 4
C61 C 0.6240(6) 0.4550(7) 0.6460(4) 0.082(3) Uani 0.400(10) 1 d DG U P B 4
H61 H 0.564014 0.455161 0.713359 0.099 Uiso 0.400(10) 1 calc R U P B 4
C62 C 0.7097(6) 0.3266(5) 0.6206(5) 0.072(2) Uani 0.400(10) 1 d DG U P B 4
H62 H 0.707044 0.240756 0.670983 0.086 Uiso 0.400(10) 1 calc R U P B 4
C63 C 0.7994(8) 0.3264(5) 0.5200(5) 0.067(2) Uani 0.400(10) 1 d DG U P B 4
C64 C 0.8034(12) 0.4546(5) 0.4447(3) 0.086(3) Uani 0.400(10) 1 d DG U P B 4
H64 H 0.863407 0.454520 0.377354 0.103 Uiso 0.400(10) 1 calc R U P B 4
C65 C 0.7177(11) 0.5831(4) 0.4701(3) 0.088(3) Uani 0.400(10) 1 d DG U P B 4
H65 H 0.720377 0.668927 0.419729 0.106 Uiso 0.400(10) 1 calc R U P B 4
C66 C 0.8952(18) 0.1870(10) 0.4894(12) 0.077(3) Uani 0.400(10) 1 d D U P B 4
H66A H 0.881283 0.107727 0.548779 0.115 Uiso 0.400(10) 1 calc R U P B 4
H66B H 0.859319 0.175206 0.431440 0.115 Uiso 0.400(10) 1 calc R U P B 4
H66C H 1.005050 0.190554 0.468951 0.115 Uiso 0.400(10) 1 calc R U P B 4


_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
N1 C2 1.4728(16) . ?
N1 C1 1.4804(16) . ?
N1 H1 0.89(2) . ?
C1 C21 1.534(2) . ?
C1 C11 1.5399(18) . ?
C1 C41 1.545(8) . ?
C1 C31 1.572(4) . ?
C2 C2 1.522(2) 2_676 ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C3 C4 1.327(3) . ?
C3 C12 1.449(3) . ?
C3 H3 0.9300 . ?
C4 C22 1.472(3) . ?
C4 H4 0.9300 . ?
C11 C16 1.387(2) . ?
C11 C12 1.412(2) . ?
C12 C13 1.409(2) . ?
C13 C14 1.364(3) . ?
C13 H13 0.9300 . ?
C14 C15 1.373(3) . ?
C14 H14 0.9300 . ?
C15 C16 1.397(2) . ?
C15 H15 0.9300 . ?
C16 H16 0.9300 . ?
C21 C26 1.393(2) . ?
C21 C22 1.411(2) . ?
C22 C23 1.400(3) . ?
C23 C24 1.375(3) . ?
C23 H23 0.9300 . ?
C24 C25 1.386(3) . ?
C24 H24 0.9300 . ?
C25 C26 1.385(2) . ?
C25 H25 0.9300 . ?
C26 H26 0.9300 . ?
C31 C32 1.3900 . ?
C31 C36 1.3900 . ?
C32 C33 1.3900 . ?
C32 H32 0.9300 . ?
C33 C34 1.3900 . ?
C33 H33 0.9300 . ?
C34 C35 1.3900 . ?
C34 H34 0.9300 . ?
C35 C36 1.3900 . ?
C35 H35 0.9300 . ?
C36 H36 0.9300 . ?
C41 C42 1.3900 . ?
C41 C46 1.3900 . ?
C42 C43 1.3900 . ?
C42 H42 0.9300 . ?
C43 C44 1.3900 . ?
C43 H43 0.9300 . ?
C44 C45 1.3900 . ?
C44 H44 0.9300 . ?
C45 C46 1.3900 . ?
C45 H45 0.9300 . ?
C46 H46 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 1.518(7) . ?
C54 C55 1.3900 . ?
C54 H54 0.9300 . ?
C55 H55 0.9300 . ?
C56 H56A 0.9600 . ?
C56 H56B 0.9600 . ?
C56 H56C 0.9600 . ?
N6 C61 1.3900 . ?
N6 C65 1.3900 . ?
C61 C62 1.3900 . ?
C61 H61 0.9300 . ?
C62 C63 1.3900 . ?
C62 H62 0.9300 . ?
C63 C64 1.3900 . ?
C63 C66 1.529(9) . ?
C64 C65 1.3900 . ?
C64 H64 0.9300 . ?
C65 H65 0.9300 . ?
C66 H66A 0.9600 . ?
C66 H66B 0.9600 . ?
C66 H66C 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
C2 N1 C1 115.92(10) . . ?
C2 N1 H1 106.0(13) . . ?
C1 N1 H1 107.9(13) . . ?
N1 C1 C21 110.22(11) . . ?
N1 C1 C11 109.13(11) . . ?
C21 C1 C11 104.73(10) . . ?
N1 C1 C41 109.7(6) . . ?
C21 C1 C41 106.6(9) . . ?
C11 C1 C41 116.3(8) . . ?
N1 C1 C31 108.0(3) . . ?
C21 C1 C31 116.4(2) . . ?
C11 C1 C31 108.1(3) . . ?
N1 C2 C2 109.62(13) . 2_676 ?
N1 C2 H2A 109.7 . . ?
C2 C2 H2A 109.7 2_676 . ?
N1 C2 H2B 109.7 . . ?
C2 C2 H2B 109.7 2_676 . ?
H2A C2 H2B 108.2 . . ?
C4 C3 C12 126.24(16) . . ?
C4 C3 H3 116.9 . . ?
C12 C3 H3 116.9 . . ?
C3 C4 C22 125.96(17) . . ?
C3 C4 H4 117.0 . . ?
C22 C4 H4 117.0 . . ?
C16 C11 C12 118.44(14) . . ?
C16 C11 C1 121.86(12) . . ?
C12 C11 C1 119.69(13) . . ?
C13 C12 C11 118.41(17) . . ?
C13 C12 C3 117.48(16) . . ?
C11 C12 C3 124.05(15) . . ?
C14 C13 C12 122.11(18) . . ?
C14 C13 H13 118.9 . . ?
C12 C13 H13 118.9 . . ?
C13 C14 C15 119.39(17) . . ?
C13 C14 H14 120.3 . . ?
C15 C14 H14 120.3 . . ?
C14 C15 C16 120.17(19) . . ?
C14 C15 H15 119.9 . . ?
C16 C15 H15 119.9 . . ?
C11 C16 C15 121.35(17) . . ?
C11 C16 H16 119.3 . . ?
C15 C16 H16 119.3 . . ?
C26 C21 C22 118.54(15) . . ?
C26 C21 C1 120.99(13) . . ?
C22 C21 C1 120.40(13) . . ?
C23 C22 C21 118.78(17) . . ?
C23 C22 C4 117.95(16) . . ?
C21 C22 C4 123.15(16) . . ?
C24 C23 C22 121.67(18) . . ?
C24 C23 H23 119.2 . . ?
C22 C23 H23 119.2 . . ?
C23 C24 C25 119.49(18) . . ?
C23 C24 H24 120.3 . . ?
C25 C24 H24 120.3 . . ?
C26 C25 C24 119.87(19) . . ?
C26 C25 H25 120.1 . . ?
C24 C25 H25 120.1 . . ?
C25 C26 C21 121.51(16) . . ?
C25 C26 H26 119.2 . . ?
C21 C26 H26 119.2 . . ?
C32 C31 C36 120.0 . . ?
C32 C31 C1 120.2(3) . . ?
C36 C31 C1 119.7(3) . . ?
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 . . ?
C35 C34 C33 120.0 . . ?
C35 C34 H34 120.0 . . ?
C33 C34 H34 120.0 . . ?
C36 C35 C34 120.0 . . ?
C36 C35 H35 120.0 . . ?
C34 C35 H35 120.0 . . ?
C35 C36 C31 120.0 . . ?
C35 C36 H36 120.0 . . ?
C31 C36 H36 120.0 . . ?
C42 C41 C46 120.0 . . ?
C42 C41 C1 114.6(8) . . ?
C46 C41 C1 125.3(8) . . ?
C43 C42 C41 120.0 . . ?
C43 C42 H42 120.0 . . ?
C41 C42 H42 120.0 . . ?
C42 C43 C44 120.0 . . ?
C42 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 C46 120.0 . . ?
C44 C45 H45 120.0 . . ?
C46 C45 H45 120.0 . . ?
C45 C46 C41 120.0 . . ?
C45 C46 H46 120.0 . . ?
C41 C46 H46 120.0 . . ?
C51 N5 C55 120.0 . . ?
N5 C51 C52 120.0 . . ?
N5 C51 H51 120.0 . . ?
C52 C51 H51 120.0 . . ?
C53 C52 C51 120.0 . . ?
C53 C52 H52 120.0 . . ?
C51 C52 H52 120.0 . . ?
C52 C53 C54 120.0 . . ?
C52 C53 C56 118.7(6) . . ?
C54 C53 C56 121.3(6) . . ?
C55 C54 C53 120.0 . . ?
C55 C54 H54 120.0 . . ?
C53 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 . . ?
C61 N6 C65 120.0 . . ?
N6 C61 C62 120.0 . . ?
N6 C61 H61 120.0 . . ?
C62 C61 H61 120.0 . . ?
C61 C62 C63 120.0 . . ?
C61 C62 H62 120.0 . . ?
C63 C62 H62 120.0 . . ?
C64 C63 C62 120.0 . . ?
C64 C63 C66 118.7(6) . . ?
C62 C63 C66 121.3(6) . . ?
C63 C64 C65 120.0 . . ?
C63 C64 H64 120.0 . . ?
C65 C64 H64 120.0 . . ?
C64 C65 N6 120.0 . . ?
C64 C65 H65 120.0 . . ?
N6 C65 H65 120.0 . . ?
C63 C66 H66A 109.5 . . ?
C63 C66 H66B 109.5 . . ?
H66A C66 H66B 109.5 . . ?
C63 C66 H66C 109.5 . . ?
H66A C66 H66C 109.5 . . ?
H66B C66 H66C 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
C2 N1 C1 C21 76.04(14) . . . . ?
C2 N1 C1 C11 -169.47(11) . . . . ?
C2 N1 C1 C41 -41.1(10) . . . . ?
C2 N1 C1 C31 -52.1(3) . . . . ?
C1 N1 C2 C2 -167.83(14) . . . 2_676 ?
C12 C3 C4 C22 0.3(3) . . . . ?
N1 C1 C11 C16 -7.93(18) . . . . ?
C21 C1 C11 C16 110.08(14) . . . . ?
C41 C1 C11 C16 -132.6(9) . . . . ?
C31 C1 C11 C16 -125.2(3) . . . . ?
N1 C1 C11 C12 171.22(12) . . . . ?
C21 C1 C11 C12 -70.78(15) . . . . ?
C41 C1 C11 C12 46.6(9) . . . . ?
C31 C1 C11 C12 53.9(3) . . . . ?
C16 C11 C12 C13 4.2(2) . . . . ?
C1 C11 C12 C13 -174.95(14) . . . . ?
C16 C11 C12 C3 -173.00(15) . . . . ?
C1 C11 C12 C3 7.8(2) . . . . ?
C4 C3 C12 C13 -141.81(19) . . . . ?
C4 C3 C12 C11 35.4(3) . . . . ?
C11 C12 C13 C14 -3.2(3) . . . . ?
C3 C12 C13 C14 174.17(19) . . . . ?
C12 C13 C14 C15 0.2(3) . . . . ?
C13 C14 C15 C16 1.8(3) . . . . ?
C12 C11 C16 C15 -2.4(2) . . . . ?
C1 C11 C16 C15 176.78(14) . . . . ?
C14 C15 C16 C11 -0.7(3) . . . . ?
N1 C1 C21 C26 9.83(17) . . . . ?
C11 C1 C21 C26 -107.42(14) . . . . ?
C41 C1 C21 C26 128.8(7) . . . . ?
C31 C1 C21 C26 133.3(3) . . . . ?
N1 C1 C21 C22 -173.16(12) . . . . ?
C11 C1 C21 C22 69.58(15) . . . . ?
C41 C1 C21 C22 -54.2(7) . . . . ?
C31 C1 C21 C22 -49.7(4) . . . . ?
C26 C21 C22 C23 -4.6(2) . . . . ?
C1 C21 C22 C23 178.28(14) . . . . ?
C26 C21 C22 C4 171.22(15) . . . . ?
C1 C21 C22 C4 -5.9(2) . . . . ?
C3 C4 C22 C23 139.1(2) . . . . ?
C3 C4 C22 C21 -36.8(3) . . . . ?
C21 C22 C23 C24 3.5(3) . . . . ?
C4 C22 C23 C24 -172.55(19) . . . . ?
C22 C23 C24 C25 -0.7(3) . . . . ?
C23 C24 C25 C26 -0.9(3) . . . . ?
C24 C25 C26 C21 -0.3(3) . . . . ?
C22 C21 C26 C25 3.1(2) . . . . ?
C1 C21 C26 C25 -179.80(14) . . . . ?
N1 C1 C31 C32 99.4(4) . . . . ?
C21 C1 C31 C32 -25.1(5) . . . . ?
C11 C1 C31 C32 -142.6(3) . . . . ?
N1 C1 C31 C36 -76.9(4) . . . . ?
C21 C1 C31 C36 158.6(3) . . . . ?
C11 C1 C31 C36 41.1(4) . . . . ?
C36 C31 C32 C33 0.0 . . . . ?
C1 C31 C32 C33 -176.3(6) . . . . ?
C31 C32 C33 C34 0.0 . . . . ?
C32 C33 C34 C35 0.0 . . . . ?
C33 C34 C35 C36 0.0 . . . . ?
C34 C35 C36 C31 0.0 . . . . ?
C32 C31 C36 C35 0.0 . . . . ?
C1 C31 C36 C35 176.3(6) . . . . ?
N1 C1 C41 C42 -83.9(8) . . . . ?
C21 C1 C41 C42 156.8(6) . . . . ?
C11 C1 C41 C42 40.5(9) . . . . ?
N1 C1 C41 C46 92.2(11) . . . . ?
C21 C1 C41 C46 -27.1(10) . . . . ?
C11 C1 C41 C46 -143.4(7) . . . . ?
C46 C41 C42 C43 0.0 . . . . ?
C1 C41 C42 C43 176.3(12) . . . . ?
C41 C42 C43 C44 0.0 . . . . ?
C42 C43 C44 C45 0.0 . . . . ?
C43 C44 C45 C46 0.0 . . . . ?
C44 C45 C46 C41 0.0 . . . . ?
C42 C41 C46 C45 0.0 . . . . ?
C1 C41 C46 C45 -175.9(13) . . . . ?
C55 N5 C51 C52 0.0 . . . . ?
N5 C51 C52 C53 0.0 . . . . ?
C51 C52 C53 C54 0.0 . . . . ?
C51 C52 C53 C56 177.0(7) . . . . ?
C52 C53 C54 C55 0.0 . . . . ?
C56 C53 C54 C55 -176.9(7) . . . . ?
C53 C54 C55 N5 0.0 . . . . ?
C51 N5 C55 C54 0.0 . . . . ?
C65 N6 C61 C62 0.0 . . . . ?
N6 C61 C62 C63 0.0 . . . . ?
C61 C62 C63 C64 0.0 . . . . ?
C61 C62 C63 C66 179.9(8) . . . . ?
C62 C63 C64 C65 0.0 . . . . ?
C66 C63 C64 C65 -180.0(8) . . . . ?
C63 C64 C65 N6 0.0 . . . . ?
C61 N6 C65 C64 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
N1 H1 N5^c 0.89(2) 2.48(2) 3.369(3) 178.0(18) . yes
C16 H16 N1 0.93 2.40 2.7715(18) 104 . yes
C26 H26 N1 0.93 2.40 2.779(2) 104 . yes

_refine_diff_density_max         0.399
_refine_diff_density_min         -0.448
_refine_diff_density_rms         0.042


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: 4-methylpyridine'
