# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# 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_E-1
_database_code_depnum_ccdc_archive 'CCDC 2248689'
loop_
_audit_author_name
_audit_author_address
'Gregor Schnakenburg'
;University of Bonn
Germany
;
_audit_update_record             
;
2023-03-14 deposited with the CCDC.	2023-04-03 downloaded from the CCDC.
;
_audit_creation_date             2023-01-20
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2017/1
_chemical_name_common            ?
_chemical_name_systematic        MN-12R
_chemical_formula_moiety         'C22 H20 N2'
_chemical_formula_sum            'C22 H20 N2'
_chemical_formula_weight         312.40
_chemical_absolute_configuration ?
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   4.96650(10)
_cell_length_b                   11.8329(2)
_cell_length_c                   27.6027(5)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1622.16(5)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    118085
_cell_measurement_temperature    100
_cell_measurement_theta_max      70.93
_cell_measurement_theta_min      3.20
_shelx_estimated_absorpt_T_max   0.924
_shelx_estimated_absorpt_T_min   0.837
_exptl_absorpt_coefficient_mu    0.576
_exptl_absorpt_correction_T_max  0.6934
_exptl_absorpt_correction_T_min  0.6362
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
STOE LANA, absorption correction by scaling of reflection intensities.
J. Koziskova, F. Hahn, J. Richter, J. Kozisek, "Comparison of different
absorption corrections on the model structure of tetrakis(μ₂-acetato)-
diaqua-di-copper(II)", Acta Chimica Slovaca, vol. 9, no. 2, 2016, pp. 136 - 140.
Afterwards a spherical absorption correction was performed within STOE LANA.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear orange'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.279
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plank
_exptl_crystal_F_000             664
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.207
_exptl_crystal_size_min          0.14
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0211
_diffrn_reflns_av_unetI/netI     0.0056
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       2
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_number            65728
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        67.686
_diffrn_reflns_theta_max         70.482
_diffrn_reflns_theta_min         3.202
_diffrn_ambient_temperature      100.15
_diffrn_detector_area_resol_mean 5.81
_diffrn_detector_type            'DECTRIS PILATUS 200K'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_details      
;
 8112 frames, detector distance = 40 mm
;
_diffrn_measurement_device       'Eulerian 4-circle diffractometer'
_diffrn_measurement_device_type  'STOE STADIVARI'
_diffrn_measurement_method       'rotation method, ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54186
_diffrn_source                   ?
_reflns_Friedel_coverage         0.677
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.989
_reflns_number_gt                3039
_reflns_number_total             3071
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       
;
X-Area Recipe 1.37.0.0 (STOE, 2021)
;
_computing_data_collection       
;
X-Area Pilatus3_SV 1.31.189.0 (STOE, 2022)
;
_computing_data_reduction        
;
X-Area Integrate 2.5.11.0 (STOE, 2022)
X-Area LANA 2.7.9.0 (STOE, 2022)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.183
_refine_diff_density_min         -0.120
_refine_diff_density_rms         0.031
_refine_ls_abs_structure_details 
;
 Flack x determined using 1224 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.02(12)
_refine_ls_extinction_coef       0.0093(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2017/1 (Sheldrick 2017)'
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     218
_refine_ls_number_reflns         3071
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0251
_refine_ls_R_factor_gt           0.0249
_refine_ls_restrained_S_all      1.050
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0350P)²+0.3007P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0641
_refine_ls_wR_factor_ref         0.0643
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B), C8(H8A,H8B), C15(H15A,H15B), C16(H16A,H16B)
2.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C5(H5), C6(H6), C10(H10), C11(H11), C12(H12), C13(H13),
 C19(H19), C20(H20), C21(H21), C22(H22)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
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 0.5491(3) 0.34230(10) 0.64770(4) 0.0219(3) Uani 1 1 d . . . . .
N2 N 0.3834(3) 0.31233(10) 0.67957(4) 0.0230(3) Uani 1 1 d . . . . .
C1 C 0.6266(3) 0.25456(11) 0.61480(5) 0.0201(3) Uani 1 1 d . . . . .
C2 C 0.8332(3) 0.28317(11) 0.58231(5) 0.0201(3) Uani 1 1 d . . . . .
C3 C 0.9172(3) 0.20180(12) 0.54906(5) 0.0228(3) Uani 1 1 d . . . . .
H3 H 1.057548 0.219215 0.526900 0.027 Uiso 1 1 calc R . . . .
C4 C 0.7983(3) 0.09558(12) 0.54793(5) 0.0241(3) Uani 1 1 d . . . . .
H4 H 0.857695 0.041067 0.525032 0.029 Uiso 1 1 calc R . . . .
C5 C 0.5925(3) 0.06857(12) 0.58015(5) 0.0244(3) Uani 1 1 d . . . . .
H5 H 0.511395 -0.004100 0.579174 0.029 Uiso 1 1 calc R . . . .
C6 C 0.5065(3) 0.14774(12) 0.61358(5) 0.0234(3) Uani 1 1 d . . . . .
H6 H 0.366233 0.129601 0.635656 0.028 Uiso 1 1 calc R . . . .
C7 C 0.9578(3) 0.39954(11) 0.58311(5) 0.0206(3) Uani 1 1 d . . . . .
H7A H 1.137918 0.396088 0.567812 0.025 Uiso 1 1 calc R . . . .
H7B H 0.982297 0.423600 0.617176 0.025 Uiso 1 1 calc R . . . .
C8 C 0.7849(3) 0.48841(11) 0.55636(5) 0.0213(3) Uani 1 1 d . . . . .
H8A H 0.811969 0.479936 0.521009 0.026 Uiso 1 1 calc R . . . .
H8B H 0.592385 0.474007 0.563345 0.026 Uiso 1 1 calc R . . . .
C9 C 0.8533(3) 0.60834(11) 0.57093(5) 0.0196(3) Uani 1 1 d . . . . .
C10 C 1.0551(3) 0.66578(12) 0.54566(5) 0.0216(3) Uani 1 1 d . . . . .
H10 H 1.142669 0.628987 0.519438 0.026 Uiso 1 1 calc R . . . .
C11 C 1.1312(3) 0.77504(12) 0.55777(5) 0.0235(3) Uani 1 1 d . . . . .
H11 H 1.270222 0.812105 0.540273 0.028 Uiso 1 1 calc R . . . .
C12 C 1.0020(3) 0.82946(12) 0.59567(5) 0.0238(3) Uani 1 1 d . . . . .
H12 H 1.051337 0.904387 0.604278 0.029 Uiso 1 1 calc R . . . .
C13 C 0.8004(3) 0.77382(12) 0.62094(5) 0.0221(3) Uani 1 1 d . . . . .
H13 H 0.711865 0.812062 0.646674 0.027 Uiso 1 1 calc R . . . .
C14 C 0.7232(3) 0.66324(11) 0.60976(5) 0.0201(3) Uani 1 1 d . . . . .
C15 C 0.5086(3) 0.60835(12) 0.64071(5) 0.0209(3) Uani 1 1 d . . . . .
H15A H 0.423315 0.546254 0.622202 0.025 Uiso 1 1 calc R . . . .
H15B H 0.367551 0.664766 0.648308 0.025 Uiso 1 1 calc R . . . .
C16 C 0.6244(3) 0.56073(11) 0.68845(5) 0.0199(3) Uani 1 1 d . . . . .
H16A H 0.763900 0.503615 0.680880 0.024 Uiso 1 1 calc R . . . .
H16B H 0.711455 0.622623 0.706816 0.024 Uiso 1 1 calc R . . . .
C17 C 0.4090(3) 0.50726(12) 0.71943(5) 0.0199(3) Uani 1 1 d . . . . .
C18 C 0.3009(3) 0.39724(11) 0.71309(5) 0.0201(3) Uani 1 1 d . . . . .
C19 C 0.0921(3) 0.35892(12) 0.74322(5) 0.0236(3) Uani 1 1 d . . . . .
H19 H 0.023125 0.284757 0.738777 0.028 Uiso 1 1 calc R . . . .
C20 C -0.0155(3) 0.42658(13) 0.77921(5) 0.0257(3) Uani 1 1 d . . . . .
H20 H -0.160908 0.400414 0.798562 0.031 Uiso 1 1 calc R . . . .
C21 C 0.0923(3) 0.53309(13) 0.78651(5) 0.0263(3) Uani 1 1 d . . . . .
H21 H 0.023908 0.579936 0.811608 0.032 Uiso 1 1 calc R . . . .
C22 C 0.3010(3) 0.57171(12) 0.75714(5) 0.0242(3) Uani 1 1 d . . . . .
H22 H 0.372839 0.644858 0.762980 0.029 Uiso 1 1 calc R . . . .


_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 N2 1.2558(17) . ?
N1 C1 1.4319(17) . ?
N2 C18 1.4260(18) . ?
C1 C2 1.404(2) . ?
C1 C6 1.3980(19) . ?
C2 C3 1.3940(19) . ?
C2 C7 1.5099(19) . ?
C3 H3 0.9500 . ?
C3 C4 1.389(2) . ?
C4 H4 0.9500 . ?
C4 C5 1.392(2) . ?
C5 H5 0.9500 . ?
C5 C6 1.383(2) . ?
C6 H6 0.9500 . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C7 C8 1.5456(19) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C8 C9 1.5136(18) . ?
C9 C10 1.398(2) . ?
C9 C14 1.4100(19) . ?
C10 H10 0.9500 . ?
C10 C11 1.388(2) . ?
C11 H11 0.9500 . ?
C11 C12 1.386(2) . ?
C12 H12 0.9500 . ?
C12 C13 1.387(2) . ?
C13 H13 0.9500 . ?
C13 C14 1.3979(19) . ?
C14 C15 1.5126(19) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C15 C16 1.5446(18) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C16 C17 1.5088(19) . ?
C17 C18 1.419(2) . ?
C17 C22 1.397(2) . ?
C18 C19 1.405(2) . ?
C19 H19 0.9500 . ?
C19 C20 1.383(2) . ?
C20 H20 0.9500 . ?
C20 C21 1.384(2) . ?
C21 H21 0.9500 . ?
C21 C22 1.393(2) . ?
C22 H22 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
N2 N1 C1 114.55(11) . . ?
N1 N2 C18 116.35(12) . . ?
C2 C1 N1 115.24(12) . . ?
C6 C1 N1 123.80(13) . . ?
C6 C1 C2 120.95(13) . . ?
C1 C2 C7 120.67(12) . . ?
C3 C2 C1 118.21(13) . . ?
C3 C2 C7 121.12(13) . . ?
C2 C3 H3 119.6 . . ?
C4 C3 C2 120.83(14) . . ?
C4 C3 H3 119.6 . . ?
C3 C4 H4 119.8 . . ?
C3 C4 C5 120.36(13) . . ?
C5 C4 H4 119.8 . . ?
C4 C5 H5 120.1 . . ?
C6 C5 C4 119.86(13) . . ?
C6 C5 H5 120.1 . . ?
C1 C6 H6 120.1 . . ?
C5 C6 C1 119.79(14) . . ?
C5 C6 H6 120.1 . . ?
C2 C7 H7A 109.1 . . ?
C2 C7 H7B 109.1 . . ?
C2 C7 C8 112.69(11) . . ?
H7A C7 H7B 107.8 . . ?
C8 C7 H7A 109.1 . . ?
C8 C7 H7B 109.1 . . ?
C7 C8 H8A 109.0 . . ?
C7 C8 H8B 109.0 . . ?
H8A C8 H8B 107.8 . . ?
C9 C8 C7 112.71(11) . . ?
C9 C8 H8A 109.0 . . ?
C9 C8 H8B 109.0 . . ?
C10 C9 C8 118.97(13) . . ?
C10 C9 C14 118.94(12) . . ?
C14 C9 C8 122.09(13) . . ?
C9 C10 H10 119.1 . . ?
C11 C10 C9 121.88(13) . . ?
C11 C10 H10 119.1 . . ?
C10 C11 H11 120.4 . . ?
C12 C11 C10 119.26(14) . . ?
C12 C11 H11 120.4 . . ?
C11 C12 H12 120.2 . . ?
C11 C12 C13 119.56(13) . . ?
C13 C12 H12 120.2 . . ?
C12 C13 H13 119.0 . . ?
C12 C13 C14 122.09(13) . . ?
C14 C13 H13 119.0 . . ?
C9 C14 C15 123.66(12) . . ?
C13 C14 C9 118.27(13) . . ?
C13 C14 C15 118.06(12) . . ?
C14 C15 H15A 109.2 . . ?
C14 C15 H15B 109.2 . . ?
C14 C15 C16 112.08(11) . . ?
H15A C15 H15B 107.9 . . ?
C16 C15 H15A 109.2 . . ?
C16 C15 H15B 109.2 . . ?
C15 C16 H16A 109.2 . . ?
C15 C16 H16B 109.2 . . ?
H16A C16 H16B 107.9 . . ?
C17 C16 C15 111.86(11) . . ?
C17 C16 H16A 109.2 . . ?
C17 C16 H16B 109.2 . . ?
C18 C17 C16 125.67(12) . . ?
C22 C17 C16 117.74(13) . . ?
C22 C17 C18 116.57(13) . . ?
C17 C18 N2 128.15(13) . . ?
C19 C18 N2 111.64(12) . . ?
C19 C18 C17 120.17(13) . . ?
C18 C19 H19 119.2 . . ?
C20 C19 C18 121.58(14) . . ?
C20 C19 H19 119.2 . . ?
C19 C20 H20 120.6 . . ?
C19 C20 C21 118.82(14) . . ?
C21 C20 H20 120.6 . . ?
C20 C21 H21 119.9 . . ?
C20 C21 C22 120.12(14) . . ?
C22 C21 H21 119.9 . . ?
C17 C22 H22 118.7 . . ?
C21 C22 C17 122.69(14) . . ?
C21 C22 H22 118.7 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 N2 C18 C17 -9.6(2) . . . . ?
N1 N2 C18 C19 172.69(12) . . . . ?
N1 C1 C2 C3 -179.61(12) . . . . ?
N1 C1 C2 C7 -0.37(19) . . . . ?
N1 C1 C6 C5 179.29(13) . . . . ?
N2 N1 C1 C2 -173.35(12) . . . . ?
N2 N1 C1 C6 7.65(19) . . . . ?
N2 C18 C19 C20 178.61(13) . . . . ?
C1 N1 N2 C18 -179.98(12) . . . . ?
C1 C2 C3 C4 0.4(2) . . . . ?
C1 C2 C7 C8 -80.30(16) . . . . ?
C2 C1 C6 C5 0.3(2) . . . . ?
C2 C3 C4 C5 -0.1(2) . . . . ?
C2 C7 C8 C9 160.45(12) . . . . ?
C3 C2 C7 C8 98.91(15) . . . . ?
C3 C4 C5 C6 -0.2(2) . . . . ?
C4 C5 C6 C1 0.1(2) . . . . ?
C6 C1 C2 C3 -0.6(2) . . . . ?
C6 C1 C2 C7 178.66(13) . . . . ?
C7 C2 C3 C4 -178.80(13) . . . . ?
C7 C8 C9 C10 88.85(15) . . . . ?
C7 C8 C9 C14 -89.98(16) . . . . ?
C8 C9 C10 C11 -178.74(13) . . . . ?
C8 C9 C14 C13 179.55(12) . . . . ?
C8 C9 C14 C15 0.9(2) . . . . ?
C9 C10 C11 C12 -0.7(2) . . . . ?
C9 C14 C15 C16 97.56(15) . . . . ?
C10 C9 C14 C13 0.72(19) . . . . ?
C10 C9 C14 C15 -177.98(12) . . . . ?
C10 C11 C12 C13 0.3(2) . . . . ?
C11 C12 C13 C14 0.6(2) . . . . ?
C12 C13 C14 C9 -1.1(2) . . . . ?
C12 C13 C14 C15 177.68(13) . . . . ?
C13 C14 C15 C16 -81.14(15) . . . . ?
C14 C9 C10 C11 0.1(2) . . . . ?
C14 C15 C16 C17 179.35(11) . . . . ?
C15 C16 C17 C18 80.18(16) . . . . ?
C15 C16 C17 C22 -98.40(14) . . . . ?
C16 C17 C18 N2 5.2(2) . . . . ?
C16 C17 C18 C19 -177.28(13) . . . . ?
C16 C17 C22 C21 176.80(13) . . . . ?
C17 C18 C19 C20 0.7(2) . . . . ?
C18 C17 C22 C21 -1.9(2) . . . . ?
C18 C19 C20 C21 -2.2(2) . . . . ?
C19 C20 C21 C22 1.6(2) . . . . ?
C20 C21 C22 C17 0.5(2) . . . . ?
C22 C17 C18 N2 -176.21(13) . . . . ?
C22 C17 C18 C19 1.32(19) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'

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