# Supplementary Information (SI) for Polymer Chemistry.
# This journal is © The Royal Society of Chemistry 2025

####################################################################### 
# 
# 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_d24115_a
_database_code_depnum_ccdc_archive 'CCDC 2429413'
loop_
_audit_author_name
_audit_author_address
'Alan J. Lough '
;University of Toronto
Canada
;
_audit_update_record             
;
2025-03-06 deposited with the CCDC.	2025-04-24 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2019/1
_shelx_SHELXL_version_number     2019/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C22 H22 N2'
_chemical_formula_sum            'C22 H22 N2'
_chemical_formula_weight         314.41

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                   6.3548(10)
_cell_length_b                   7.1946(12)
_cell_length_c                   19.210(3)
_cell_angle_alpha                90
_cell_angle_beta                 91.006(6)
_cell_angle_gamma                90
_cell_volume                     878.2(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    9265
_cell_measurement_theta_min      2.83
_cell_measurement_theta_max      27.50

_exptl_crystal_description       Shard
_exptl_crystal_colour            orange
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.189
_exptl_crystal_F_000             336
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.310
_exptl_crystal_size_mid          0.270
_exptl_crystal_size_min          0.140
_exptl_absorpt_coefficient_mu    0.070
_shelx_estimated_absorpt_T_min   0.979
_shelx_estimated_absorpt_T_max   0.990
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7078
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   'SADABS (Krause et al., 2015)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed tube with Bruker Triumph monochromator'
_diffrn_measurement_device_type  'Bruker Kappa APEX-DUO CMOD PHOTON II'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            14238
_diffrn_reflns_av_unetI/netI     0.0143
_diffrn_reflns_av_R_equivalents  0.0216
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         2.121
_diffrn_reflns_theta_max         27.500
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             2011
_reflns_number_gt                1826
_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       'APEX4 (Bruker AXS, 2021)'
_computing_cell_refinement       APEX4
_computing_data_reduction        APEX4
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2015a)'
_computing_structure_refinement  'SHELXL-2019/1 (Sheldrick, 2015b)'
_computing_molecular_graphics    'PLATON (Spek, 2009)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_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)+(0.0572P)²+0.2903P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ditect
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2011
_refine_ls_number_parameters     110
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0425
_refine_ls_R_factor_gt           0.0390
_refine_ls_wR_factor_ref         0.1128
_refine_ls_wR_factor_gt          0.1092
_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
N1 N 0.54860(14) 0.33088(13) 0.63111(4) 0.0214(2) Uani 1 1 d . . . . .
C1 C 0.45058(17) 0.92591(14) 0.51398(5) 0.0216(2) Uani 1 1 d . . . . .
H1 H 0.302855 0.914700 0.506737 0.026 Uiso 1 1 calc R U . . .
C2 C 0.55675(17) 0.78502(14) 0.55390(5) 0.0219(2) Uani 1 1 d . . . . .
H2A H 0.702400 0.803953 0.563385 0.026 Uiso 1 1 calc R U . . .
C3 C 0.47033(16) 0.62719(15) 0.57955(5) 0.0214(2) Uani 1 1 d . . . . .
C4 C 0.24174(17) 0.57759(16) 0.57323(6) 0.0257(3) Uani 1 1 d . . . . .
H4A H 0.186036 0.553605 0.619621 0.039 Uiso 1 1 calc R U . . .
H4B H 0.225480 0.465954 0.544404 0.039 Uiso 1 1 calc R U . . .
H4C H 0.164218 0.680783 0.551530 0.039 Uiso 1 1 calc R U . . .
C5 C 0.61133(17) 0.49227(15) 0.61220(5) 0.0222(2) Uani 1 1 d . . . . .
H5A H 0.754769 0.524910 0.619764 0.027 Uiso 1 1 calc R U . . .
C6 C 0.70009(16) 0.20043(14) 0.65530(5) 0.0203(2) Uani 1 1 d . . . . .
C7 C 0.64241(17) 0.07536(15) 0.70738(5) 0.0234(2) Uani 1 1 d . . . . .
H7A H 0.505044 0.080682 0.726012 0.028 Uiso 1 1 calc R U . . .
C8 C 0.78476(19) -0.05633(16) 0.73196(6) 0.0271(3) Uani 1 1 d . . . . .
H8A H 0.745279 -0.138965 0.768021 0.033 Uiso 1 1 calc R U . . .
C9 C 0.98465(19) -0.06818(17) 0.70418(6) 0.0290(3) Uani 1 1 d . . . . .
H9A H 1.081676 -0.158637 0.721112 0.035 Uiso 1 1 calc R U . . .
C10 C 1.04196(17) 0.05328(17) 0.65138(6) 0.0274(3) Uani 1 1 d . . . . .
H10A H 1.178198 0.045214 0.632021 0.033 Uiso 1 1 calc R U . . .
C11 C 0.90084(17) 0.18588(15) 0.62699(6) 0.0234(2) Uani 1 1 d . . . . .
H11A H 0.940713 0.267700 0.590715 0.028 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C5 1.2822(14) . ?
N1 C6 1.4170(13) . ?
C1 C1 1.353(2) 3_676 ?
C1 C2 1.4328(15) . ?
C1 H1 0.9500 . ?
C2 C3 1.3576(15) . ?
C2 H2A 0.9500 . ?
C3 C5 1.4556(15) . ?
C3 C4 1.4987(15) . ?
C4 H4A 0.9800 . ?
C4 H4B 0.9800 . ?
C4 H4C 0.9800 . ?
C5 H5A 0.9500 . ?
C6 C7 1.3992(15) . ?
C6 C11 1.3995(15) . ?
C7 C8 1.3870(16) . ?
C7 H7A 0.9500 . ?
C8 C9 1.3890(18) . ?
C8 H8A 0.9500 . ?
C9 C10 1.3922(17) . ?
C9 H9A 0.9500 . ?
C10 C11 1.3853(16) . ?
C10 H10A 0.9500 . ?
C11 H11A 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
C5 N1 C6 118.68(9) . . ?
C1 C1 C2 123.52(13) 3_676 . ?
C1 C1 H1 118.2 3_676 . ?
C2 C1 H1 118.2 . . ?
C3 C2 C1 126.60(10) . . ?
C3 C2 H2A 116.7 . . ?
C1 C2 H2A 116.7 . . ?
C2 C3 C5 117.66(10) . . ?
C2 C3 C4 124.57(10) . . ?
C5 C3 C4 117.68(9) . . ?
C3 C4 H4A 109.5 . . ?
C3 C4 H4B 109.5 . . ?
H4A C4 H4B 109.5 . . ?
C3 C4 H4C 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
N1 C5 C3 122.27(10) . . ?
N1 C5 H5A 118.9 . . ?
C3 C5 H5A 118.9 . . ?
C7 C6 C11 118.80(10) . . ?
C7 C6 N1 118.39(9) . . ?
C11 C6 N1 122.74(9) . . ?
C8 C7 C6 120.34(10) . . ?
C8 C7 H7A 119.8 . . ?
C6 C7 H7A 119.8 . . ?
C7 C8 C9 120.43(10) . . ?
C7 C8 H8A 119.8 . . ?
C9 C8 H8A 119.8 . . ?
C8 C9 C10 119.61(10) . . ?
C8 C9 H9A 120.2 . . ?
C10 C9 H9A 120.2 . . ?
C11 C10 C9 120.17(10) . . ?
C11 C10 H10A 119.9 . . ?
C9 C10 H10A 119.9 . . ?
C10 C11 C6 120.61(10) . . ?
C10 C11 H11A 119.7 . . ?
C6 C11 H11A 119.7 . . ?

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
C1 C1 C2 C3 -175.44(12) 3_676 . . . ?
C1 C2 C3 C5 173.31(10) . . . . ?
C1 C2 C3 C4 -3.27(18) . . . . ?
C6 N1 C5 C3 173.02(9) . . . . ?
C2 C3 C5 N1 -172.24(10) . . . . ?
C4 C3 C5 N1 4.58(15) . . . . ?
C5 N1 C6 C7 146.46(10) . . . . ?
C5 N1 C6 C11 -36.67(15) . . . . ?
C11 C6 C7 C8 2.14(16) . . . . ?
N1 C6 C7 C8 179.13(9) . . . . ?
C6 C7 C8 C9 -1.34(17) . . . . ?
C7 C8 C9 C10 0.06(17) . . . . ?
C8 C9 C10 C11 0.38(17) . . . . ?
C9 C10 C11 C6 0.45(17) . . . . ?
C7 C6 C11 C10 -1.70(16) . . . . ?
N1 C6 C11 C10 -178.56(10) . . . . ?

_refine_diff_density_max         0.260
_refine_diff_density_min         -0.239
_refine_diff_density_rms         0.042



_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: methanol'
