# Electronic Supplementary Material (ESI) for Journal of Materials Chemistry C.
# 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_a
_database_code_depnum_ccdc_archive 'CCDC 1845385'
_audit_update_record             
;
2018-05-25 deposited with the CCDC.
2018-08-13 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C13 H11 N'
_chemical_formula_weight         181.23

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           Monoclinic
_symmetry_space_group_name_H-M   'P2(1)/c  '

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

_cell_length_a                   19.2078(18)
_cell_length_b                   5.731(3)
_cell_length_c                   19.5573(14)
_cell_angle_alpha                90.00
_cell_angle_beta                 113.257(9)
_cell_angle_gamma                90.00
_cell_volume                     1977.8(10)
_cell_formula_units_Z            8
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    679
_cell_measurement_theta_min      2.52
_cell_measurement_theta_max      18.18

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.29
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.217
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             768
_exptl_absorpt_coefficient_mu    0.071
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.980
_exptl_absorpt_correction_T_max  0.986
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            9397
_diffrn_reflns_av_R_equivalents  0.0703
_diffrn_reflns_av_sigmaI/netI    0.1182
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.27
_diffrn_reflns_theta_max         25.00
_reflns_number_total             3470
_reflns_number_gt                1387
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.0030P)²+0.0052P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3470
_refine_ls_number_parameters     253
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1685
_refine_ls_R_factor_gt           0.0648
_refine_ls_wR_factor_ref         0.1559
_refine_ls_wR_factor_gt          0.1303
_refine_ls_goodness_of_fit_ref   0.967
_refine_ls_restrained_S_all      0.967
_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 0.37098(15) 0.7038(4) 0.20349(13) 0.0765(7) Uani 1 1 d . . .
N2 N 0.11318(17) -0.1402(5) 0.42973(14) 0.0830(8) Uani 1 1 d . . .
C1 C 0.41536(17) 0.6967(6) 0.16213(17) 0.0738(8) Uani 1 1 d . . .
C2 C 0.47167(19) 0.5400(6) 0.16648(19) 0.0911(10) Uani 1 1 d . . .
H2A H 0.4853 0.4180 0.2006 0.109 Uiso 1 1 calc R . .
C3 C 0.50634(19) 0.5731(7) 0.1182(2) 0.1026(11) Uani 1 1 d . . .
H3A H 0.5442 0.4698 0.1196 0.123 Uiso 1 1 calc R . .
C4 C 0.4874(2) 0.7533(8) 0.0676(2) 0.1015(12) Uani 1 1 d . . .
H4A H 0.5124 0.7695 0.0357 0.122 Uiso 1 1 calc R . .
C5 C 0.43176(19) 0.9091(6) 0.06386(17) 0.0898(10) Uani 1 1 d . . .
H5A H 0.4191 1.0309 0.0297 0.108 Uiso 1 1 calc R . .
C6 C 0.39424(16) 0.8835(6) 0.11191(16) 0.0708(8) Uani 1 1 d . . .
C7 C 0.33344(17) 1.0045(6) 0.12164(15) 0.0689(8) Uani 1 1 d . . .
C8 C 0.32061(17) 0.8858(6) 0.17824(16) 0.0703(8) Uani 1 1 d . . .
C9 C 0.26392(19) 0.9570(6) 0.20107(17) 0.0834(9) Uani 1 1 d . . .
H9A H 0.2558 0.8786 0.2389 0.100 Uiso 1 1 calc R . .
C10 C 0.22074(18) 1.1437(7) 0.1667(2) 0.0915(10) Uani 1 1 d . . .
H10A H 0.1827 1.1935 0.1815 0.110 Uiso 1 1 calc R . .
C11 C 0.23222(18) 1.2630(6) 0.10946(19) 0.0939(11) Uani 1 1 d . . .
H11A H 0.2018 1.3900 0.0864 0.113 Uiso 1 1 calc R . .
C12 C 0.28844(19) 1.1920(6) 0.08744(17) 0.0841(9) Uani 1 1 d . . .
H12A H 0.2961 1.2707 0.0494 0.101 Uiso 1 1 calc R . .
C13 C 0.37707(17) 0.5397(5) 0.26245(17) 0.1009(11) Uani 1 1 d . . .
H13A H 0.3406 0.5792 0.2829 0.151 Uiso 1 1 calc R . .
H13B H 0.4272 0.5472 0.3009 0.151 Uiso 1 1 calc R . .
H13C H 0.3674 0.3844 0.2424 0.151 Uiso 1 1 calc R . .
C14 C 0.2785(2) 0.1773(9) 0.3795(2) 0.1072(12) Uani 1 1 d . . .
H14A H 0.3149 0.2570 0.3683 0.129 Uiso 1 1 calc R . .
C15 C 0.2987(2) -0.0227(9) 0.4223(2) 0.1105(13) Uani 1 1 d . . .
H15A H 0.3481 -0.0777 0.4380 0.133 Uiso 1 1 calc R . .
C16 C 0.2478(2) -0.1423(6) 0.44225(17) 0.0920(10) Uani 1 1 d . . .
H16A H 0.2618 -0.2755 0.4717 0.110 Uiso 1 1 calc R . .
C17 C 0.1745(2) -0.0558(6) 0.41650(17) 0.0770(9) Uani 1 1 d . . .
C18 C 0.1518(2) 0.1430(6) 0.37206(16) 0.0774(9) Uani 1 1 d . . .
C19 C 0.2056(2) 0.2599(6) 0.35337(17) 0.0975(11) Uani 1 1 d . . .
H19A H 0.1922 0.3923 0.3235 0.117 Uiso 1 1 calc R . .
C20 C 0.0731(2) 0.1783(6) 0.35563(17) 0.0788(9) Uani 1 1 d . . .
C21 C 0.0517(2) -0.0002(6) 0.39270(17) 0.0792(9) Uani 1 1 d . . .
C22 C -0.0218(2) -0.0151(6) 0.38965(18) 0.0928(10) Uani 1 1 d . . .
H22A H -0.0354 -0.1316 0.4151 0.111 Uiso 1 1 calc R . .
C23 C -0.0734(2) 0.1478(8) 0.3478(2) 0.1032(11) Uani 1 1 d . . .
H23A H -0.1230 0.1403 0.3447 0.124 Uiso 1 1 calc R . .
C24 C -0.0534(2) 0.3235(7) 0.31007(19) 0.1002(11) Uani 1 1 d . . .
H24A H -0.0896 0.4313 0.2820 0.120 Uiso 1 1 calc R . .
C25 C 0.0192(2) 0.3386(6) 0.31406(17) 0.0903(10) Uani 1 1 d . . .
H25A H 0.0323 0.4568 0.2888 0.108 Uiso 1 1 calc R . .
C26 C 0.11556(18) -0.3338(6) 0.47887(17) 0.1029(11) Uani 1 1 d . . .
H26A H 0.0660 -0.3580 0.4785 0.154 Uiso 1 1 calc R . .
H26B H 0.1505 -0.2982 0.5286 0.154 Uiso 1 1 calc R . .
H26C H 0.1317 -0.4726 0.4619 0.154 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 C8 1.375(3) . ?
N1 C1 1.388(3) . ?
N1 C13 1.457(3) . ?
N2 C21 1.374(4) . ?
N2 C17 1.389(4) . ?
N2 C26 1.456(4) . ?
C1 C2 1.382(4) . ?
C1 C6 1.400(4) . ?
C2 C3 1.367(4) . ?
C2 H2A 0.9300 . ?
C3 C4 1.377(4) . ?
C3 H3A 0.9300 . ?
C4 C5 1.372(4) . ?
C4 H4A 0.9300 . ?
C5 C6 1.399(4) . ?
C5 H5A 0.9300 . ?
C6 C7 1.434(4) . ?
C7 C12 1.376(4) . ?
C7 C8 1.402(4) . ?
C8 C9 1.391(4) . ?
C9 C10 1.358(4) . ?
C9 H9A 0.9300 . ?
C10 C11 1.402(4) . ?
C10 H10A 0.9300 . ?
C11 C12 1.373(4) . ?
C11 H11A 0.9300 . ?
C12 H12A 0.9300 . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C14 C19 1.372(4) . ?
C14 C15 1.381(5) . ?
C14 H14A 0.9300 . ?
C15 C16 1.371(4) . ?
C15 H15A 0.9300 . ?
C16 C17 1.387(4) . ?
C16 H16A 0.9300 . ?
C17 C18 1.394(4) . ?
C18 C19 1.397(4) . ?
C18 C20 1.429(4) . ?
C19 H19A 0.9300 . ?
C20 C25 1.383(4) . ?
C20 C21 1.406(4) . ?
C21 C22 1.392(4) . ?
C22 C23 1.372(4) . ?
C22 H22A 0.9300 . ?
C23 C24 1.390(4) . ?
C23 H23A 0.9300 . ?
C24 C25 1.369(4) . ?
C24 H24A 0.9300 . ?
C25 H25A 0.9300 . ?
C26 H26A 0.9600 . ?
C26 H26B 0.9600 . ?
C26 H26C 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
C8 N1 C1 108.7(2) . . ?
C8 N1 C13 126.8(3) . . ?
C1 N1 C13 124.5(3) . . ?
C21 N2 C17 108.3(3) . . ?
C21 N2 C26 126.1(3) . . ?
C17 N2 C26 125.5(3) . . ?
C2 C1 N1 129.0(3) . . ?
C2 C1 C6 122.9(3) . . ?
N1 C1 C6 108.2(3) . . ?
C3 C2 C1 116.8(3) . . ?
C3 C2 H2A 121.6 . . ?
C1 C2 H2A 121.6 . . ?
C2 C3 C4 122.6(3) . . ?
C2 C3 H3A 118.7 . . ?
C4 C3 H3A 118.7 . . ?
C5 C4 C3 120.4(3) . . ?
C5 C4 H4A 119.8 . . ?
C3 C4 H4A 119.8 . . ?
C4 C5 C6 119.5(3) . . ?
C4 C5 H5A 120.2 . . ?
C6 C5 H5A 120.2 . . ?
C5 C6 C1 117.9(3) . . ?
C5 C6 C7 134.5(3) . . ?
C1 C6 C7 107.6(3) . . ?
C12 C7 C8 119.4(3) . . ?
C12 C7 C6 134.6(3) . . ?
C8 C7 C6 106.0(3) . . ?
N1 C8 C9 129.5(3) . . ?
N1 C8 C7 109.5(3) . . ?
C9 C8 C7 121.0(3) . . ?
C10 C9 C8 118.3(3) . . ?
C10 C9 H9A 120.8 . . ?
C8 C9 H9A 120.8 . . ?
C9 C10 C11 121.4(3) . . ?
C9 C10 H10A 119.3 . . ?
C11 C10 H10A 119.3 . . ?
C12 C11 C10 119.8(3) . . ?
C12 C11 H11A 120.1 . . ?
C10 C11 H11A 120.1 . . ?
C11 C12 C7 120.0(3) . . ?
C11 C12 H12A 120.0 . . ?
C7 C12 H12A 120.0 . . ?
N1 C13 H13A 109.5 . . ?
N1 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
N1 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C19 C14 C15 120.9(4) . . ?
C19 C14 H14A 119.6 . . ?
C15 C14 H14A 119.6 . . ?
C16 C15 C14 121.8(4) . . ?
C16 C15 H15A 119.1 . . ?
C14 C15 H15A 119.1 . . ?
C15 C16 C17 117.0(4) . . ?
C15 C16 H16A 121.5 . . ?
C17 C16 H16A 121.5 . . ?
C16 C17 N2 128.5(4) . . ?
C16 C17 C18 122.8(3) . . ?
N2 C17 C18 108.7(3) . . ?
C17 C18 C19 118.2(3) . . ?
C17 C18 C20 107.4(3) . . ?
C19 C18 C20 134.4(4) . . ?
C14 C19 C18 119.3(4) . . ?
C14 C19 H19A 120.3 . . ?
C18 C19 H19A 120.3 . . ?
C25 C20 C21 118.8(3) . . ?
C25 C20 C18 134.9(4) . . ?
C21 C20 C18 106.2(3) . . ?
N2 C21 C22 129.2(4) . . ?
N2 C21 C20 109.3(3) . . ?
C22 C21 C20 121.4(3) . . ?
C23 C22 C21 117.8(3) . . ?
C23 C22 H22A 121.1 . . ?
C21 C22 H22A 121.1 . . ?
C22 C23 C24 121.6(4) . . ?
C22 C23 H23A 119.2 . . ?
C24 C23 H23A 119.2 . . ?
C25 C24 C23 120.3(4) . . ?
C25 C24 H24A 119.8 . . ?
C23 C24 H24A 119.8 . . ?
C24 C25 C20 120.1(3) . . ?
C24 C25 H25A 119.9 . . ?
C20 C25 H25A 119.9 . . ?
N2 C26 H26A 109.5 . . ?
N2 C26 H26B 109.5 . . ?
H26A C26 H26B 109.5 . . ?
N2 C26 H26C 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.162
_refine_diff_density_min         -0.188
_refine_diff_density_rms         0.039
####################################################################### 
# 
# 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_a_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 1845386'
_audit_update_record             
;
2018-05-25 deposited with the CCDC.
2018-08-13 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            C3CZ
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C15 H15 N'
_chemical_formula_weight         209.28

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           Monoclinic
_symmetry_space_group_name_H-M   'P2(1)/c  '

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

_cell_length_a                   5.455(4)
_cell_length_b                   12.3116(19)
_cell_length_c                   17.4777(13)
_cell_angle_alpha                90.00
_cell_angle_beta                 97.756(14)
_cell_angle_gamma                90.00
_cell_volume                     1163.1(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    1417
_cell_measurement_theta_min      2.35
_cell_measurement_theta_max      23.69

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.33
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.21
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.195
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             448
_exptl_absorpt_coefficient_mu    0.069
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.9775
_exptl_absorpt_correction_T_max  0.9856
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            5682
_diffrn_reflns_av_R_equivalents  0.0403
_diffrn_reflns_av_sigmaI/netI    0.0518
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         2.03
_diffrn_reflns_theta_max         25.00
_reflns_number_total             2045
_reflns_number_gt                1457
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.0200P)²+0.1300P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.028(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2045
_refine_ls_number_parameters     146
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0603
_refine_ls_R_factor_gt           0.0399
_refine_ls_wR_factor_ref         0.0957
_refine_ls_wR_factor_gt          0.0892
_refine_ls_goodness_of_fit_ref   1.095
_refine_ls_restrained_S_all      1.095
_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 0.4494(2) 0.87934(10) 0.18959(7) 0.0530(4) Uani 1 1 d . . .
C1 C 0.2556(3) 0.80904(12) 0.16605(9) 0.0510(4) Uani 1 1 d . . .
C2 C 0.1686(3) 0.77157(14) 0.09274(9) 0.0649(5) Uani 1 1 d . . .
H2A H 0.2405 0.7938 0.0501 0.078 Uiso 1 1 calc R . .
C3 C -0.0258(4) 0.70102(16) 0.08503(11) 0.0769(6) Uani 1 1 d . . .
H3A H -0.0863 0.6747 0.0362 0.092 Uiso 1 1 calc R . .
C4 C -0.1355(3) 0.66755(15) 0.14809(13) 0.0774(6) Uani 1 1 d . . .
H4A H -0.2679 0.6193 0.1410 0.093 Uiso 1 1 calc R . .
C5 C -0.0503(3) 0.70503(13) 0.22111(10) 0.0659(5) Uani 1 1 d . . .
H5A H -0.1246 0.6826 0.2633 0.079 Uiso 1 1 calc R . .
C6 C 0.1479(3) 0.77660(12) 0.23089(9) 0.0503(4) Uani 1 1 d . . .
C7 C 0.2853(3) 0.82907(12) 0.29671(8) 0.0493(4) Uani 1 1 d . . .
C8 C 0.4709(3) 0.89055(12) 0.26891(9) 0.0491(4) Uani 1 1 d . . .
C9 C 0.6445(3) 0.94840(13) 0.31816(10) 0.0618(5) Uani 1 1 d . . .
H9A H 0.7675 0.9888 0.2993 0.074 Uiso 1 1 calc R . .
C10 C 0.6278(3) 0.94369(15) 0.39575(10) 0.0700(5) Uani 1 1 d . . .
H10A H 0.7435 0.9809 0.4300 0.084 Uiso 1 1 calc R . .
C11 C 0.4439(4) 0.88528(15) 0.42445(10) 0.0701(5) Uani 1 1 d . . .
H11A H 0.4369 0.8843 0.4773 0.084 Uiso 1 1 calc R . .
C12 C 0.2716(3) 0.82868(14) 0.37555(9) 0.0614(5) Uani 1 1 d . . .
H12A H 0.1467 0.7904 0.3950 0.074 Uiso 1 1 calc R . .
C13 C 0.6044(3) 0.93414(14) 0.14009(9) 0.0629(5) Uani 1 1 d . . .
H13A H 0.5912 0.8963 0.0910 0.075 Uiso 1 1 calc R . .
H13B H 0.7754 0.9299 0.1638 0.075 Uiso 1 1 calc R . .
C14 C 0.5370(3) 1.05172(15) 0.12537(11) 0.0731(5) Uani 1 1 d . . .
H14A H 0.5572 1.0899 0.1744 0.088 Uiso 1 1 calc R . .
H14B H 0.6522 1.0832 0.0939 0.088 Uiso 1 1 calc R . .
C15 C 0.2795(4) 1.07047(17) 0.08608(11) 0.0888(6) Uani 1 1 d . . .
H15A H 0.2512 1.1471 0.0794 0.133 Uiso 1 1 calc R . .
H15B H 0.1633 1.0409 0.1171 0.133 Uiso 1 1 calc R . .
H15C H 0.2590 1.0355 0.0365 0.133 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 C8 1.3825(18) . ?
N1 C1 1.3852(19) . ?
N1 C13 1.455(2) . ?
C1 C2 1.384(2) . ?
C1 C6 1.403(2) . ?
C2 C3 1.363(2) . ?
C2 H2A 0.9300 . ?
C3 C4 1.386(3) . ?
C3 H3A 0.9300 . ?
C4 C5 1.378(2) . ?
C4 H4A 0.9300 . ?
C5 C6 1.387(2) . ?
C5 H5A 0.9300 . ?
C6 C7 1.439(2) . ?
C7 C12 1.390(2) . ?
C7 C8 1.402(2) . ?
C8 C9 1.388(2) . ?
C9 C10 1.373(2) . ?
C9 H9A 0.9300 . ?
C10 C11 1.383(3) . ?
C10 H10A 0.9300 . ?
C11 C12 1.372(2) . ?
C11 H11A 0.9300 . ?
C12 H12A 0.9300 . ?
C13 C14 1.507(2) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C14 C15 1.495(3) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 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
C8 N1 C1 108.56(12) . . ?
C8 N1 C13 124.93(13) . . ?
C1 N1 C13 126.50(13) . . ?
C2 C1 N1 129.48(15) . . ?
C2 C1 C6 121.62(15) . . ?
N1 C1 C6 108.89(13) . . ?
C3 C2 C1 117.96(17) . . ?
C3 C2 H2A 121.0 . . ?
C1 C2 H2A 121.0 . . ?
C2 C3 C4 121.64(17) . . ?
C2 C3 H3A 119.2 . . ?
C4 C3 H3A 119.2 . . ?
C5 C4 C3 120.59(17) . . ?
C5 C4 H4A 119.7 . . ?
C3 C4 H4A 119.7 . . ?
C4 C5 C6 119.15(17) . . ?
C4 C5 H5A 120.4 . . ?
C6 C5 H5A 120.4 . . ?
C5 C6 C1 119.04(14) . . ?
C5 C6 C7 134.19(15) . . ?
C1 C6 C7 106.75(13) . . ?
C12 C7 C8 118.90(14) . . ?
C12 C7 C6 134.35(15) . . ?
C8 C7 C6 106.74(13) . . ?
N1 C8 C9 129.18(15) . . ?
N1 C8 C7 109.03(13) . . ?
C9 C8 C7 121.77(15) . . ?
C10 C9 C8 117.40(16) . . ?
C10 C9 H9A 121.3 . . ?
C8 C9 H9A 121.3 . . ?
C9 C10 C11 121.93(16) . . ?
C9 C10 H10A 119.0 . . ?
C11 C10 H10A 119.0 . . ?
C12 C11 C10 120.51(17) . . ?
C12 C11 H11A 119.7 . . ?
C10 C11 H11A 119.7 . . ?
C11 C12 C7 119.45(16) . . ?
C11 C12 H12A 120.3 . . ?
C7 C12 H12A 120.3 . . ?
N1 C13 C14 113.51(14) . . ?
N1 C13 H13A 108.9 . . ?
C14 C13 H13A 108.9 . . ?
N1 C13 H13B 108.9 . . ?
C14 C13 H13B 108.9 . . ?
H13A C13 H13B 107.7 . . ?
C15 C14 C13 114.77(16) . . ?
C15 C14 H14A 108.6 . . ?
C13 C14 H14A 108.6 . . ?
C15 C14 H14B 108.6 . . ?
C13 C14 H14B 108.6 . . ?
H14A C14 H14B 107.6 . . ?
C14 C15 H15A 109.5 . . ?
C14 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C14 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C8 N1 C1 C2 -178.41(15) . . . . ?
C13 N1 C1 C2 2.3(2) . . . . ?
C8 N1 C1 C6 1.30(16) . . . . ?
C13 N1 C1 C6 -177.95(13) . . . . ?
N1 C1 C2 C3 179.30(15) . . . . ?
C6 C1 C2 C3 -0.4(2) . . . . ?
C1 C2 C3 C4 0.3(3) . . . . ?
C2 C3 C4 C5 0.0(3) . . . . ?
C3 C4 C5 C6 -0.2(3) . . . . ?
C4 C5 C6 C1 0.2(2) . . . . ?
C4 C5 C6 C7 -178.47(16) . . . . ?
C2 C1 C6 C5 0.1(2) . . . . ?
N1 C1 C6 C5 -179.59(12) . . . . ?
C2 C1 C6 C7 179.11(13) . . . . ?
N1 C1 C6 C7 -0.62(16) . . . . ?
C5 C6 C7 C12 -0.4(3) . . . . ?
C1 C6 C7 C12 -179.16(16) . . . . ?
C5 C6 C7 C8 178.47(16) . . . . ?
C1 C6 C7 C8 -0.28(15) . . . . ?
C1 N1 C8 C9 176.75(14) . . . . ?
C13 N1 C8 C9 -4.0(2) . . . . ?
C1 N1 C8 C7 -1.48(16) . . . . ?
C13 N1 C8 C7 177.78(13) . . . . ?
C12 C7 C8 N1 -179.84(13) . . . . ?
C6 C7 C8 N1 1.07(15) . . . . ?
C12 C7 C8 C9 1.8(2) . . . . ?
C6 C7 C8 C9 -177.31(13) . . . . ?
N1 C8 C9 C10 -178.28(14) . . . . ?
C7 C8 C9 C10 -0.3(2) . . . . ?
C8 C9 C10 C11 -1.0(2) . . . . ?
C9 C10 C11 C12 0.6(3) . . . . ?
C10 C11 C12 C7 1.0(2) . . . . ?
C8 C7 C12 C11 -2.1(2) . . . . ?
C6 C7 C12 C11 176.67(15) . . . . ?
C8 N1 C13 C14 -77.13(19) . . . . ?
C1 N1 C13 C14 102.00(18) . . . . ?
N1 C13 C14 C15 -60.7(2) . . . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.114
_refine_diff_density_min         -0.118
_refine_diff_density_rms         0.027
####################################################################### 
# 
# 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_a_CCDC2
_database_code_depnum_ccdc_archive 'CCDC 1845387'
_audit_update_record             
;
2018-05-25 deposited with the CCDC.
2018-08-13 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C17 H19 N'
_chemical_formula_weight         237.33

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   Pbca

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

_cell_length_a                   15.959(2)
_cell_length_b                   7.5700(10)
_cell_length_c                   22.1950(10)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     2681.4(5)
_cell_formula_units_Z            8
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    646
_cell_measurement_theta_min      2.24
_cell_measurement_theta_max      19.21

_exptl_crystal_description       rod
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.33
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.21
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.176
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1024
_exptl_absorpt_coefficient_mu    0.068
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.9780
_exptl_absorpt_correction_T_max  0.9859
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            12465
_diffrn_reflns_av_R_equivalents  0.1275
_diffrn_reflns_av_sigmaI/netI    0.1474
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_theta_min         2.24
_diffrn_reflns_theta_max         25.00
_reflns_number_total             2342
_reflns_number_gt                1419
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.0060P)²+0.2000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.009(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2342
_refine_ls_number_parameters     164
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1086
_refine_ls_R_factor_gt           0.0609
_refine_ls_wR_factor_ref         0.1649
_refine_ls_wR_factor_gt          0.1412
_refine_ls_goodness_of_fit_ref   0.971
_refine_ls_restrained_S_all      0.971
_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 0.07010(11) 0.5428(3) 0.13287(8) 0.0322(5) Uani 1 1 d . . .
C1 C 0.10348(14) 0.6354(3) 0.18064(9) 0.0305(6) Uani 1 1 d . . .
C2 C 0.18030(14) 0.6133(3) 0.20856(10) 0.0352(6) Uani 1 1 d . . .
H2A H 0.2185 0.5249 0.1956 0.042 Uiso 1 1 calc R . .
C3 C 0.19940(15) 0.7239(4) 0.25574(11) 0.0426(7) Uani 1 1 d . . .
H3A H 0.2520 0.7127 0.2754 0.051 Uiso 1 1 calc R . .
C4 C 0.14308(16) 0.8517(4) 0.27520(11) 0.0443(7) Uani 1 1 d . . .
H4A H 0.1573 0.9252 0.3084 0.053 Uiso 1 1 calc R . .
C5 C 0.06743(16) 0.8730(4) 0.24721(11) 0.0409(7) Uani 1 1 d . . .
H5A H 0.0295 0.9616 0.2605 0.049 Uiso 1 1 calc R . .
C6 C 0.04684(14) 0.7652(3) 0.19971(10) 0.0341(6) Uani 1 1 d . . .
C7 C -0.02468(15) 0.7501(3) 0.16072(10) 0.0345(6) Uani 1 1 d . . .
C8 C -0.00812(14) 0.6119(3) 0.12048(10) 0.0362(7) Uani 1 1 d . . .
C9 C -0.06541(16) 0.5602(4) 0.07717(11) 0.0457(7) Uani 1 1 d . . .
H9A H -0.0543 0.4645 0.0507 0.055 Uiso 1 1 calc R . .
C10 C -0.13945(17) 0.6540(5) 0.07416(12) 0.0575(9) Uani 1 1 d . . .
H10A H -0.1800 0.6226 0.0447 0.069 Uiso 1 1 calc R . .
C11 C -0.15593(18) 0.7916(5) 0.11268(13) 0.0606(9) Uani 1 1 d . . .
H11A H -0.2076 0.8531 0.1093 0.073 Uiso 1 1 calc R . .
C12 C -0.09954(16) 0.8424(4) 0.15597(12) 0.0493(8) Uani 1 1 d . . .
H12A H -0.1115 0.9385 0.1821 0.059 Uiso 1 1 calc R . .
C13 C 0.10986(15) 0.3953(3) 0.10225(10) 0.0352(6) Uani 1 1 d . . .
H13A H 0.1702 0.4216 0.0972 0.042 Uiso 1 1 calc R . .
H13B H 0.0851 0.3834 0.0616 0.042 Uiso 1 1 calc R . .
C14 C 0.10073(16) 0.2215(3) 0.13518(10) 0.0376(7) Uani 1 1 d . . .
H14A H 0.0405 0.1951 0.1409 0.045 Uiso 1 1 calc R . .
H14B H 0.1269 0.2312 0.1755 0.045 Uiso 1 1 calc R . .
C15 C 0.14172(15) 0.0709(4) 0.10054(11) 0.0402(7) Uani 1 1 d . . .
H15A H 0.1978 0.1094 0.0868 0.048 Uiso 1 1 calc R . .
H15B H 0.1496 -0.0306 0.1281 0.048 Uiso 1 1 calc R . .
C16 C 0.09176(15) 0.0110(4) 0.04670(11) 0.0421(7) Uani 1 1 d . . .
H16A H 0.0831 0.1125 0.0192 0.050 Uiso 1 1 calc R . .
H16B H 0.0360 -0.0302 0.0603 0.050 Uiso 1 1 calc R . .
C17 C 0.13512(17) -0.1374(4) 0.01246(13) 0.0576(8) Uani 1 1 d . . .
H17A H 0.1007 -0.1718 -0.0222 0.086 Uiso 1 1 calc R . .
H17B H 0.1425 -0.2392 0.0392 0.086 Uiso 1 1 calc R . .
H17C H 0.1900 -0.0966 -0.0017 0.086 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 C1 1.378(3) . ?
N1 C8 1.381(3) . ?
N1 C13 1.453(3) . ?
C1 C2 1.384(3) . ?
C1 C6 1.401(3) . ?
C2 C3 1.375(3) . ?
C2 H2A 0.9500 . ?
C3 C4 1.389(4) . ?
C3 H3A 0.9500 . ?
C4 C5 1.367(3) . ?
C4 H4A 0.9500 . ?
C5 C6 1.373(3) . ?
C5 H5A 0.9500 . ?
C6 C7 1.437(3) . ?
C7 C12 1.388(3) . ?
C7 C8 1.401(3) . ?
C8 C9 1.383(3) . ?
C9 C10 1.380(4) . ?
C9 H9A 0.9500 . ?
C10 C11 1.373(4) . ?
C10 H10A 0.9500 . ?
C11 C12 1.371(4) . ?
C11 H11A 0.9500 . ?
C12 H12A 0.9500 . ?
C13 C14 1.512(3) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C14 C15 1.523(3) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C15 C16 1.506(3) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C16 C17 1.523(3) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 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 C8 108.1(2) . . ?
C1 N1 C13 125.57(19) . . ?
C8 N1 C13 126.3(2) . . ?
N1 C1 C2 128.7(2) . . ?
N1 C1 C6 109.9(2) . . ?
C2 C1 C6 121.4(2) . . ?
C3 C2 C1 117.7(2) . . ?
C3 C2 H2A 121.2 . . ?
C1 C2 H2A 121.2 . . ?
C2 C3 C4 121.1(2) . . ?
C2 C3 H3A 119.4 . . ?
C4 C3 H3A 119.4 . . ?
C5 C4 C3 120.8(2) . . ?
C5 C4 H4A 119.6 . . ?
C3 C4 H4A 119.6 . . ?
C4 C5 C6 119.3(2) . . ?
C4 C5 H5A 120.3 . . ?
C6 C5 H5A 120.3 . . ?
C5 C6 C1 119.6(2) . . ?
C5 C6 C7 134.4(2) . . ?
C1 C6 C7 106.0(2) . . ?
C12 C7 C8 119.3(2) . . ?
C12 C7 C6 133.6(2) . . ?
C8 C7 C6 107.1(2) . . ?
N1 C8 C9 129.0(2) . . ?
N1 C8 C7 109.1(2) . . ?
C9 C8 C7 122.0(2) . . ?
C10 C9 C8 117.0(3) . . ?
C10 C9 H9A 121.5 . . ?
C8 C9 H9A 121.5 . . ?
C11 C10 C9 121.6(3) . . ?
C11 C10 H10A 119.2 . . ?
C9 C10 H10A 119.2 . . ?
C12 C11 C10 121.5(3) . . ?
C12 C11 H11A 119.2 . . ?
C10 C11 H11A 119.2 . . ?
C11 C12 C7 118.5(3) . . ?
C11 C12 H12A 120.8 . . ?
C7 C12 H12A 120.8 . . ?
N1 C13 C14 113.62(18) . . ?
N1 C13 H13A 108.8 . . ?
C14 C13 H13A 108.8 . . ?
N1 C13 H13B 108.8 . . ?
C14 C13 H13B 108.8 . . ?
H13A C13 H13B 107.7 . . ?
C13 C14 C15 111.48(19) . . ?
C13 C14 H14A 109.3 . . ?
C15 C14 H14A 109.3 . . ?
C13 C14 H14B 109.3 . . ?
C15 C14 H14B 109.3 . . ?
H14A C14 H14B 108.0 . . ?
C16 C15 C14 113.5(2) . . ?
C16 C15 H15A 108.9 . . ?
C14 C15 H15A 108.9 . . ?
C16 C15 H15B 108.9 . . ?
C14 C15 H15B 108.9 . . ?
H15A C15 H15B 107.7 . . ?
C15 C16 C17 112.2(2) . . ?
C15 C16 H16A 109.2 . . ?
C17 C16 H16A 109.2 . . ?
C15 C16 H16B 109.2 . . ?
C17 C16 H16B 109.2 . . ?
H16A C16 H16B 107.9 . . ?
C16 C17 H17A 109.5 . . ?
C16 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C16 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?

_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.996
_refine_diff_density_max         0.223
_refine_diff_density_min         -0.231
_refine_diff_density_rms         0.052
