# Electronic Supplementary Material (ESI) for Polymer Chemistry.
# This journal is © The Royal Society of Chemistry 2018

####################################################################### 
# 
# 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_buch210a
_database_code_depnum_ccdc_archive 'CCDC 1842215'
_audit_update_record             
;
2018-05-09 deposited with the CCDC.
2018-06-18 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 Compound 6 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C23 H30 N2'
_chemical_formula_sum            'C23 H30 N2'
_chemical_formula_weight         334.49

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'P b c n'
_symmetry_space_group_name_Hall  '-P 2n 2ab'

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

_cell_length_a                   15.5646(19)
_cell_length_b                   7.8895(9)
_cell_length_c                   15.9608(17)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1959.9(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    130(2)
_cell_measurement_reflns_used    1719
_cell_measurement_theta_min      2.55
_cell_measurement_theta_max      28.39

_exptl_crystal_description       plate
_exptl_crystal_colour            light-yellow
_exptl_crystal_size_max          0.57
_exptl_crystal_size_mid          0.56
_exptl_crystal_size_min          0.09
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.134
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             728
_exptl_absorpt_coefficient_mu    0.066
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7197
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_process_details   'Blessing, 1995'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      130(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  Triumph
_diffrn_measurement_device_type  'Bruker Kappa APEXII Duo'
_diffrn_measurement_method       'Omega + Phi Scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        0
_diffrn_reflns_number            16113
_diffrn_reflns_av_R_equivalents  0.0331
_diffrn_reflns_av_sigmaI/netI    0.0268
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         2.55
_diffrn_reflns_theta_max         28.39
_reflns_number_total             2448
_reflns_number_gt                1719
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEXII Software Suite, 2008'
_computing_cell_refinement       'Bruker APEXII Software Suite, 2008'
_computing_data_reduction        'Bruker APEXII Software Suite, 2008'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'SHELXTL-plus, xP (Sheldrick, 1991)'
_computing_publication_material  ?

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0920P)²+0.5832P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2448
_refine_ls_number_parameters     132
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0830
_refine_ls_R_factor_gt           0.0551
_refine_ls_wR_factor_ref         0.1664
_refine_ls_wR_factor_gt          0.1529
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_restrained_S_all      1.051
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.04059(10) 0.36660(18) 0.68811(9) 0.0347(4) Uani 1 1 d . A 1
C1 C 0.0000 0.2717(3) 0.7500 0.0264(5) Uani 1 2 d S . 1
C2 C 0.03832(18) 0.5507(2) 0.68433(14) 0.0517(7) Uani 1 1 d D . 1
H2A H 0.0958(11) 0.595(3) 0.6777(15) 0.062 Uiso 1 1 d D B 1
H2B H 0.0155(14) 0.581(3) 0.6282(12) 0.062 Uiso 1 1 d D C 1
C3 C 0.0438(3) 0.6242(5) 0.7744(2) 0.0449(10) Uani 0.50 1 d P . 1
H3A H 0.0398 0.7531 0.7748 0.054 Uiso 0.50 1 d P D 1
H3B H 0.1031 0.5632 0.7982 0.054 Uiso 0.50 1 d P E 1
C4 C 0.0000 0.1016(3) 0.7500 0.0308(5) Uani 1 2 d S . .
H4A H 0.0294(13) 0.038(3) 0.7100(13) 0.045(6) Uiso 1 1 d . . .
C5 C 0.08268(10) 0.28251(19) 0.62009(9) 0.0233(3) Uani 1 1 d . . .
C6 C 0.03706(10) 0.24457(19) 0.54740(10) 0.0245(4) Uani 1 1 d . A .
C7 C 0.08031(10) 0.16695(19) 0.48123(9) 0.0235(3) Uani 1 1 d . . .
H7 H 0.0495 0.1394 0.4317 0.028 Uiso 1 1 calc R A .
C8 C 0.16730(10) 0.1288(2) 0.48585(9) 0.0227(3) Uani 1 1 d . A .
C9 C 0.21103(10) 0.1675(2) 0.55929(9) 0.0259(4) Uani 1 1 d . . .
H9 H 0.2704 0.1407 0.5635 0.031 Uiso 1 1 calc R A .
C10 C 0.17017(10) 0.2445(2) 0.62682(9) 0.0259(4) Uani 1 1 d . A .
C11 C -0.05721(11) 0.2865(2) 0.54070(13) 0.0373(4) Uani 1 1 d . . .
H11A H -0.0862 0.2555 0.5930 0.056 Uiso 1 1 calc R A .
H11B H -0.0826 0.2229 0.4941 0.056 Uiso 1 1 calc R . .
H11C H -0.0641 0.4082 0.5306 0.056 Uiso 1 1 calc R . .
C12 C 0.21369(11) 0.0477(2) 0.41303(10) 0.0325(4) Uani 1 1 d . . .
H12A H 0.1718 0.0133 0.3704 0.049 Uiso 1 1 calc R A .
H12B H 0.2452 -0.0522 0.4327 0.049 Uiso 1 1 calc R . .
H12C H 0.2541 0.1292 0.3887 0.049 Uiso 1 1 calc R . .
C13 C 0.21885(13) 0.2852(3) 0.70608(11) 0.0421(5) Uani 1 1 d . . .
H13A H 0.1974 0.2143 0.7519 0.063 Uiso 1 1 calc R A .
H13B H 0.2106 0.4050 0.7203 0.063 Uiso 1 1 calc R . .
H13C H 0.2802 0.2628 0.6975 0.063 Uiso 1 1 calc R . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
N1 0.0544(9) 0.0168(7) 0.0328(7) -0.0002(6) 0.0265(7) -0.0012(6)
C1 0.0342(12) 0.0218(11) 0.0231(10) 0.000 0.0129(9) 0.000
C2 0.0829(16) 0.0199(10) 0.0524(12) 0.0019(8) 0.0412(12) -0.0030(10)
C3 0.073(3) 0.0175(16) 0.044(2) -0.0058(15) 0.0277(19) -0.0074(17)
C4 0.0435(14) 0.0200(11) 0.0288(11) 0.000 0.0181(10) 0.000
C5 0.0301(8) 0.0170(8) 0.0228(7) 0.0017(6) 0.0112(6) 0.0009(6)
C6 0.0227(7) 0.0165(7) 0.0344(8) 0.0039(6) 0.0046(6) -0.0016(6)
C7 0.0277(7) 0.0201(8) 0.0227(7) 0.0023(6) -0.0019(6) -0.0033(6)
C8 0.0294(8) 0.0194(8) 0.0192(7) 0.0003(6) 0.0078(6) -0.0018(6)
C9 0.0218(7) 0.0290(9) 0.0268(7) 0.0006(6) 0.0025(6) 0.0020(6)
C10 0.0324(8) 0.0252(8) 0.0200(7) 0.0013(6) 0.0002(6) -0.0002(7)
C11 0.0242(8) 0.0291(10) 0.0588(11) 0.0028(8) 0.0033(8) 0.0018(7)
C12 0.0397(9) 0.0308(9) 0.0270(8) -0.0055(7) 0.0145(7) -0.0033(7)
C13 0.0540(11) 0.0460(12) 0.0264(8) -0.0059(8) -0.0090(8) 0.0045(9)

_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 C1 1.3910(18) . ?
N1 C5 1.4312(18) . ?
N1 C2 1.454(2) . ?
C1 C4 1.342(3) . ?
C1 N1 1.3910(18) 3_556 ?
C2 C3 1.550(4) 3_556 ?
C2 C3 1.553(4) . ?
C2 H2A 0.967(16) . ?
C2 H2B 0.992(16) . ?
C3 C2 1.550(4) 3_556 ?
C3 C3 1.571(10) 3_556 ?
C3 H3A 1.0188 . ?
C3 H3B 1.1078 . ?
C4 H4A 0.93(2) . ?
C5 C6 1.393(2) . ?
C5 C10 1.398(2) . ?
C6 C7 1.394(2) . ?
C6 C11 1.508(2) . ?
C7 C8 1.389(2) . ?
C7 H7 0.9500 . ?
C8 C9 1.389(2) . ?
C8 C12 1.511(2) . ?
C9 C10 1.391(2) . ?
C9 H9 0.9500 . ?
C10 C13 1.509(2) . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 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
C1 N1 C5 119.81(14) . . ?
C1 N1 C2 123.77(14) . . ?
C5 N1 C2 116.27(13) . . ?
C4 C1 N1 122.55(10) . 3_556 ?
C4 C1 N1 122.55(10) . . ?
N1 C1 N1 114.89(19) 3_556 . ?
N1 C2 C3 112.1(2) . 3_556 ?
N1 C2 C3 109.5(2) . . ?
C3 C2 C3 60.8(3) 3_556 . ?
N1 C2 H2A 110.1(15) . . ?
C3 C2 H2A 132.4(15) 3_556 . ?
C3 C2 H2A 85.2(14) . . ?
N1 C2 H2B 106.4(15) . . ?
C3 C2 H2B 89.9(14) 3_556 . ?
C3 C2 H2B 140.1(15) . . ?
H2A C2 H2B 98.5(18) . . ?
C2 C3 C2 102.0(3) 3_556 . ?
C2 C3 C3 59.7(3) 3_556 3_556 ?
C2 C3 C3 59.5(3) . 3_556 ?
C2 C3 H3A 108.7 3_556 . ?
C2 C3 H3A 112.0 . . ?
C3 C3 H3A 87.1 3_556 . ?
C2 C3 H3B 112.3 3_556 . ?
C2 C3 H3B 101.6 . . ?
C3 C3 H3B 153.3 3_556 . ?
H3A C3 H3B 118.9 . . ?
C1 C4 H4A 122.5(13) . . ?
C6 C5 C10 120.95(13) . . ?
C6 C5 N1 119.88(14) . . ?
C10 C5 N1 119.13(14) . . ?
C5 C6 C7 118.64(14) . . ?
C5 C6 C11 120.53(14) . . ?
C7 C6 C11 120.82(15) . . ?
C8 C7 C6 121.71(14) . . ?
C8 C7 H7 119.1 . . ?
C6 C7 H7 119.1 . . ?
C7 C8 C9 118.34(13) . . ?
C7 C8 C12 121.12(14) . . ?
C9 C8 C12 120.54(14) . . ?
C8 C9 C10 121.72(14) . . ?
C8 C9 H9 119.1 . . ?
C10 C9 H9 119.1 . . ?
C9 C10 C5 118.63(14) . . ?
C9 C10 C13 120.85(15) . . ?
C5 C10 C13 120.51(14) . . ?
C6 C11 H11A 109.5 . . ?
C6 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C6 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C8 C12 H12A 109.5 . . ?
C8 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C8 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C10 C13 H13A 109.5 . . ?
C10 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C10 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 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
C5 N1 C1 C4 1.52(18) . . . . ?
C2 N1 C1 C4 177.05(17) . . . . ?
C5 N1 C1 N1 -178.47(18) . . . 3_556 ?
C2 N1 C1 N1 -2.95(17) . . . 3_556 ?
C1 N1 C2 C3 -27.4(3) . . . 3_556 ?
C5 N1 C2 C3 148.2(2) . . . 3_556 ?
C1 N1 C2 C3 38.1(3) . . . . ?
C5 N1 C2 C3 -146.3(2) . . . . ?
N1 C2 C3 C2 -61.5(3) . . . 3_556 ?
C3 C2 C3 C2 43.6(3) 3_556 . . 3_556 ?
N1 C2 C3 C3 -105.0(2) . . . 3_556 ?
C1 N1 C5 C6 89.75(18) . . . . ?
C2 N1 C5 C6 -86.1(2) . . . . ?
C1 N1 C5 C10 -92.30(18) . . . . ?
C2 N1 C5 C10 91.9(2) . . . . ?
C10 C5 C6 C7 0.3(2) . . . . ?
N1 C5 C6 C7 178.20(13) . . . . ?
C10 C5 C6 C11 -179.84(15) . . . . ?
N1 C5 C6 C11 -1.9(2) . . . . ?
C5 C6 C7 C8 -0.7(2) . . . . ?
C11 C6 C7 C8 179.38(15) . . . . ?
C6 C7 C8 C9 1.0(2) . . . . ?
C6 C7 C8 C12 -178.84(14) . . . . ?
C7 C8 C9 C10 -0.8(2) . . . . ?
C12 C8 C9 C10 179.04(15) . . . . ?
C8 C9 C10 C5 0.4(2) . . . . ?
C8 C9 C10 C13 179.88(16) . . . . ?
C6 C5 C10 C9 -0.1(2) . . . . ?
N1 C5 C10 C9 -178.02(14) . . . . ?
C6 C5 C10 C13 -179.62(15) . . . . ?
N1 C5 C10 C13 2.4(2) . . . . ?

_diffrn_measured_fraction_theta_max 0.992
_diffrn_reflns_theta_full        28.39
_diffrn_measured_fraction_theta_full 0.992
_refine_diff_density_max         0.478
_refine_diff_density_min         -0.193
_refine_diff_density_rms         0.050
