# Electronic Supplementary Material (ESI) for Chemical Communications.
# This journal is © The Royal Society of Chemistry 2017

####################################################################### 
# 
# 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_130418_qya_7_155
_database_code_depnum_ccdc_archive 'CCDC 1407535'
_audit_update_record             
;
2015-06-18 deposited with the CCDC.
2017-03-15 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C26 H29 N'
_chemical_formula_sum            'C26 H29 N'
_chemical_formula_weight         355.50

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           Triclinic
_symmetry_space_group_name_H-M   'P -1'
_symmetry_space_group_name_Hall  '-P 1'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.9286(13)
_cell_length_b                   12.8700(11)
_cell_length_c                   17.6090(15)
_cell_angle_alpha                87.421(7)
_cell_angle_beta                 81.658(9)
_cell_angle_gamma                86.987(9)
_cell_volume                     1997.9(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    170(2)
_cell_measurement_reflns_used    3041
_cell_measurement_theta_min      3.1660
_cell_measurement_theta_max      29.6724

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.32
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.182
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             768
_exptl_absorpt_coefficient_mu    0.067
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9703
_exptl_absorpt_correction_T_max  0.9788
_exptl_absorpt_process_details   
;
CrysAlis PRO (Agilent Technologies, 2011) 
;

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      170(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  'Xcalibur, Atlas, Gemini ultra'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 10.3592
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            12777
_diffrn_reflns_av_R_equivalents  0.0434
_diffrn_reflns_av_sigmaI/netI    0.0672
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         3.17
_diffrn_reflns_theta_max         25.35
_reflns_number_total             7297
_reflns_number_gt                5057
_reflns_threshold_expression     >2sigma(I)

_computing_cell_refinement       'CrysAlis PRO (Agilent Technologies, 2011)'
_computing_data_collection       'CrysAlis PRO'
_computing_data_reduction        'CrysAlis PRO'
_computing_molecular_graphics    'OLEX2 (Dolomanov et al., 2009)'
_computing_publication_material  OLEX2
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'

_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)+(0.0950P)²+10.9448P] 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         7297
_refine_ls_number_parameters     495
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1312
_refine_ls_R_factor_gt           0.0993
_refine_ls_wR_factor_ref         0.3412
_refine_ls_wR_factor_gt          0.3233
_refine_ls_goodness_of_fit_ref   1.133
_refine_ls_restrained_S_all      1.133
_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 0.5882(5) 0.7203(3) 0.2722(2) 0.0264(10) Uani 1 1 d . . .
N2 N 0.7724(5) 0.0533(3) 0.2151(2) 0.0274(10) Uani 1 1 d . . .
C1 C 0.5128(6) 0.8143(4) 0.2913(3) 0.0287(12) Uani 1 1 d . . .
C2 C 0.4590(6) 0.8897(4) 0.2412(4) 0.0349(13) Uani 1 1 d . . .
H2 H 0.4733 0.8816 0.1872 0.042 Uiso 1 1 calc R . .
C3 C 0.3828(7) 0.9778(5) 0.2746(4) 0.0419(15) Uani 1 1 d . . .
H3 H 0.3448 1.0314 0.2426 0.050 Uiso 1 1 calc R . .
C4 C 0.3616(7) 0.9885(5) 0.3538(4) 0.0404(15) Uani 1 1 d . . .
H4 H 0.3075 1.0485 0.3749 0.048 Uiso 1 1 calc R . .
C5 C 0.4181(7) 0.9129(4) 0.4029(4) 0.0371(14) Uani 1 1 d . . .
H5 H 0.4038 0.9214 0.4568 0.044 Uiso 1 1 calc R . .
C6 C 0.4963(6) 0.8243(4) 0.3713(3) 0.0286(12) Uani 1 1 d . . .
C7 C 0.5661(6) 0.7299(4) 0.4023(3) 0.0292(12) Uani 1 1 d . . .
C8 C 0.6171(6) 0.6657(4) 0.3397(3) 0.0264(11) Uani 1 1 d . . .
C9 C 0.6797(6) 0.5644(4) 0.3508(3) 0.0277(12) Uani 1 1 d . . .
C10 C 0.7010(6) 0.5342(4) 0.4262(3) 0.0332(13) Uani 1 1 d . . .
C11 C 0.6575(6) 0.5992(5) 0.4888(3) 0.0317(13) Uani 1 1 d . . .
C12 C 0.5872(6) 0.6969(5) 0.4770(3) 0.0322(13) Uani 1 1 d . . .
C13 C 0.6267(6) 0.6922(5) 0.1926(3) 0.0303(12) Uani 1 1 d . . .
H13A H 0.7170 0.6436 0.1881 0.036 Uiso 1 1 calc R . .
H13B H 0.6541 0.7556 0.1608 0.036 Uiso 1 1 calc R . .
C14 C 0.5002(6) 0.6416(4) 0.1607(3) 0.0289(12) Uani 1 1 d . . .
C15 C 0.5033(7) 0.6392(5) 0.0814(3) 0.0365(14) Uani 1 1 d . . .
H15 H 0.5818 0.6716 0.0478 0.044 Uiso 1 1 calc R . .
C16 C 0.3914(8) 0.5894(5) 0.0515(4) 0.0443(16) Uani 1 1 d . . .
H16 H 0.3927 0.5888 -0.0025 0.053 Uiso 1 1 calc R . .
C17 C 0.2789(7) 0.5411(5) 0.0998(4) 0.0420(15) Uani 1 1 d . . .
H17 H 0.2040 0.5061 0.0790 0.050 Uiso 1 1 calc R . .
C18 C 0.2742(7) 0.5432(5) 0.1783(4) 0.0402(15) Uani 1 1 d . . .
H18 H 0.1959 0.5100 0.2114 0.048 Uiso 1 1 calc R . .
C19 C 0.3836(6) 0.5937(5) 0.2092(3) 0.0353(13) Uani 1 1 d . . .
H19 H 0.3792 0.5958 0.2633 0.042 Uiso 1 1 calc R . .
C20 C 0.7136(6) 0.4884(4) 0.2867(3) 0.0317(13) Uani 1 1 d . . .
H20A H 0.6506 0.5100 0.2464 0.038 Uiso 1 1 calc R . .
H20B H 0.6818 0.4189 0.3074 0.038 Uiso 1 1 calc R . .
C21 C 0.8792(6) 0.4777(5) 0.2491(3) 0.0344(13) Uani 1 1 d . . .
H21A H 0.9126 0.5472 0.2292 0.041 Uiso 1 1 calc R . .
H21B H 0.9426 0.4535 0.2887 0.041 Uiso 1 1 calc R . .
C22 C 0.9055(7) 0.4023(5) 0.1833(3) 0.0372(14) Uani 1 1 d . . .
H22A H 0.8586 0.3359 0.2012 0.045 Uiso 1 1 calc R . .
H22B H 1.0158 0.3874 0.1697 0.045 Uiso 1 1 calc R . .
C23 C 0.8407(9) 0.4435(6) 0.1113(4) 0.0536(18) Uani 1 1 d . . .
H23A H 0.8625 0.3921 0.0713 0.080 Uiso 1 1 calc R . .
H23B H 0.8874 0.5089 0.0928 0.080 Uiso 1 1 calc R . .
H23C H 0.7309 0.4559 0.1238 0.080 Uiso 1 1 calc R . .
C24 C 0.7749(8) 0.4284(5) 0.4425(4) 0.0444(16) Uani 1 1 d . . .
H24A H 0.7889 0.3883 0.3958 0.067 Uiso 1 1 calc R . .
H24B H 0.7099 0.3912 0.4833 0.067 Uiso 1 1 calc R . .
H24C H 0.8736 0.4375 0.4588 0.067 Uiso 1 1 calc R . .
C25 C 0.6842(8) 0.5594(6) 0.5679(4) 0.0483(17) Uani 1 1 d . . .
H25A H 0.6494 0.6128 0.6052 0.072 Uiso 1 1 calc R . .
H25B H 0.7926 0.5431 0.5680 0.072 Uiso 1 1 calc R . .
H25C H 0.6278 0.4963 0.5819 0.072 Uiso 1 1 calc R . .
C26 C 0.5318(8) 0.7698(6) 0.5419(4) 0.0484(17) Uani 1 1 d . . .
H26A H 0.4208 0.7736 0.5507 0.073 Uiso 1 1 calc R . .
H26B H 0.5690 0.8394 0.5279 0.073 Uiso 1 1 calc R . .
H26C H 0.5700 0.7433 0.5888 0.073 Uiso 1 1 calc R . .
C27 C 0.6710(6) 0.1304(4) 0.1938(3) 0.0262(11) Uani 1 1 d . . .
C28 C 0.5967(7) 0.2087(4) 0.2385(3) 0.0354(13) Uani 1 1 d . . .
H28 H 0.6144 0.2157 0.2899 0.043 Uiso 1 1 calc R . .
C29 C 0.4958(7) 0.2764(5) 0.2059(4) 0.0405(15) Uani 1 1 d . . .
H29 H 0.4433 0.3305 0.2354 0.049 Uiso 1 1 calc R . .
C30 C 0.4706(7) 0.2664(5) 0.1308(4) 0.0392(15) Uani 1 1 d . . .
H30 H 0.4005 0.3136 0.1099 0.047 Uiso 1 1 calc R . .
C31 C 0.5455(7) 0.1887(4) 0.0855(4) 0.0357(14) Uani 1 1 d . . .
H31 H 0.5278 0.1832 0.0339 0.043 Uiso 1 1 calc R . .
C32 C 0.6473(6) 0.1187(4) 0.1169(3) 0.0282(12) Uani 1 1 d . . .
C33 C 0.7405(6) 0.0268(4) 0.0905(3) 0.0288(12) Uani 1 1 d . . .
C34 C 0.8154(6) -0.0111(4) 0.1527(3) 0.0255(11) Uani 1 1 d . . .
C35 C 0.9220(6) -0.0952(4) 0.1456(3) 0.0280(12) Uani 1 1 d . . .
C36 C 0.9391(7) -0.1467(4) 0.0763(3) 0.0325(13) Uani 1 1 d . . .
C37 C 0.8590(6) -0.1124(4) 0.0145(3) 0.0292(12) Uani 1 1 d . . .
C38 C 0.7648(6) -0.0236(4) 0.0201(3) 0.0289(12) Uani 1 1 d . . .
C39 C 0.7760(7) 0.0263(4) 0.2967(3) 0.0293(12) Uani 1 1 d . . .
H39A H 0.8069 -0.0484 0.3019 0.035 Uiso 1 1 calc R . .
H39B H 0.6720 0.0359 0.3247 0.035 Uiso 1 1 calc R . .
C40 C 0.8807(6) 0.0886(4) 0.3345(3) 0.0285(12) Uani 1 1 d . . .
C41 C 0.9816(7) 0.1572(5) 0.2955(3) 0.0368(14) Uani 1 1 d . . .
H41 H 0.9906 0.1653 0.2412 0.044 Uiso 1 1 calc R . .
C42 C 1.0702(7) 0.2147(5) 0.3360(4) 0.0445(16) Uani 1 1 d . . .
H42 H 1.1382 0.2624 0.3089 0.053 Uiso 1 1 calc R . .
C43 C 1.0604(8) 0.2032(5) 0.4144(4) 0.0477(17) Uani 1 1 d . . .
H43 H 1.1207 0.2428 0.4415 0.057 Uiso 1 1 calc R . .
C44 C 0.9627(8) 0.1342(6) 0.4528(4) 0.0517(18) Uani 1 1 d . . .
H44 H 0.9563 0.1252 0.5070 0.062 Uiso 1 1 calc R . .
C45 C 0.8727(8) 0.0770(5) 0.4141(3) 0.0413(15) Uani 1 1 d . . .
H45 H 0.8051 0.0296 0.4419 0.050 Uiso 1 1 calc R . .
C46 C 1.0228(6) -0.1213(4) 0.2067(3) 0.0309(12) Uani 1 1 d . . .
H46A H 1.0246 -0.0587 0.2373 0.037 Uiso 1 1 calc R . .
H46B H 1.1273 -0.1355 0.1806 0.037 Uiso 1 1 calc R . .
C47 C 0.9802(7) -0.2133(4) 0.2624(3) 0.0326(13) Uani 1 1 d . . .
H47A H 0.8726 -0.2039 0.2854 0.039 Uiso 1 1 calc R . .
H47B H 0.9918 -0.2784 0.2338 0.039 Uiso 1 1 calc R . .
C48 C 1.0788(7) -0.2225(5) 0.3259(3) 0.0391(14) Uani 1 1 d . . .
H48A H 1.0645 -0.1578 0.3550 0.047 Uiso 1 1 calc R . .
H48B H 1.1865 -0.2288 0.3024 0.047 Uiso 1 1 calc R . .
C49 C 1.0444(9) -0.3154(5) 0.3816(4) 0.0498(17) Uani 1 1 d . . .
H49A H 1.0674 -0.3801 0.3541 0.075 Uiso 1 1 calc R . .
H49B H 0.9370 -0.3114 0.4035 0.075 Uiso 1 1 calc R . .
H49C H 1.1067 -0.3143 0.4230 0.075 Uiso 1 1 calc R . .
C50 C 1.0473(7) -0.2409(5) 0.0653(4) 0.0394(14) Uani 1 1 d . . .
H50A H 1.1051 -0.2493 0.1086 0.059 Uiso 1 1 calc R . .
H50B H 1.1171 -0.2314 0.0174 0.059 Uiso 1 1 calc R . .
H50C H 0.9898 -0.3032 0.0627 0.059 Uiso 1 1 calc R . .
C51 C 0.8897(8) -0.1727(5) -0.0583(4) 0.0434(15) Uani 1 1 d . . .
H51A H 0.8199 -0.1469 -0.0937 0.065 Uiso 1 1 calc R . .
H51B H 0.8749 -0.2468 -0.0458 0.065 Uiso 1 1 calc R . .
H51C H 0.9944 -0.1636 -0.0826 0.065 Uiso 1 1 calc R . .
C52 C 0.6959(7) 0.0231(5) -0.0474(3) 0.0369(14) Uani 1 1 d . . .
H52A H 0.7578 0.0016 -0.0952 0.055 Uiso 1 1 calc R . .
H52B H 0.6918 0.0992 -0.0455 0.055 Uiso 1 1 calc R . .
H52C H 0.5930 -0.0010 -0.0454 0.055 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 1.384(7) . ?
N1 C8 1.403(7) . ?
N1 C13 1.451(7) . ?
N2 C27 1.383(7) . ?
N2 C34 1.404(7) . ?
N2 C39 1.468(7) . ?
C1 C2 1.396(8) . ?
C1 C6 1.406(8) . ?
C2 C3 1.400(9) . ?
C2 H2 0.9500 . ?
C3 C4 1.393(9) . ?
C3 H3 0.9500 . ?
C4 C5 1.395(9) . ?
C4 H4 0.9500 . ?
C5 C6 1.399(8) . ?
C5 H5 0.9500 . ?
C6 C7 1.457(8) . ?
C7 C12 1.399(8) . ?
C7 C8 1.414(8) . ?
C8 C9 1.408(7) . ?
C9 C10 1.404(8) . ?
C9 C20 1.514(7) . ?
C10 C11 1.410(8) . ?
C10 C24 1.515(8) . ?
C11 C12 1.396(8) . ?
C11 C25 1.510(8) . ?
C12 C26 1.522(8) . ?
C13 C14 1.519(8) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C14 C15 1.395(8) . ?
C14 C19 1.398(8) . ?
C15 C16 1.392(9) . ?
C15 H15 0.9500 . ?
C16 C17 1.374(10) . ?
C16 H16 0.9500 . ?
C17 C18 1.379(9) . ?
C17 H17 0.9500 . ?
C18 C19 1.387(8) . ?
C18 H18 0.9500 . ?
C19 H19 0.9500 . ?
C20 C21 1.532(8) . ?
C20 H20A 0.9900 . ?
C20 H20B 0.9900 . ?
C21 C22 1.529(8) . ?
C21 H21A 0.9900 . ?
C21 H21B 0.9900 . ?
C22 C23 1.531(9) . ?
C22 H22A 0.9900 . ?
C22 H22B 0.9900 . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 0.9800 . ?
C24 H24A 0.9800 . ?
C24 H24B 0.9800 . ?
C24 H24C 0.9800 . ?
C25 H25A 0.9800 . ?
C25 H25B 0.9800 . ?
C25 H25C 0.9800 . ?
C26 H26A 0.9800 . ?
C26 H26B 0.9800 . ?
C26 H26C 0.9800 . ?
C27 C28 1.387(8) . ?
C27 C32 1.416(7) . ?
C28 C29 1.387(9) . ?
C28 H28 0.9500 . ?
C29 C30 1.385(9) . ?
C29 H29 0.9500 . ?
C30 C31 1.390(8) . ?
C30 H30 0.9500 . ?
C31 C32 1.400(8) . ?
C31 H31 0.9500 . ?
C32 C33 1.463(8) . ?
C33 C38 1.408(8) . ?
C33 C34 1.420(7) . ?
C34 C35 1.400(8) . ?
C35 C36 1.400(8) . ?
C35 C46 1.516(7) . ?
C36 C37 1.428(8) . ?
C36 C50 1.511(8) . ?
C37 C38 1.382(8) . ?
C37 C51 1.512(8) . ?
C38 C52 1.503(8) . ?
C39 C40 1.506(8) . ?
C39 H39A 0.9900 . ?
C39 H39B 0.9900 . ?
C40 C41 1.383(8) . ?
C40 C45 1.394(8) . ?
C41 C42 1.398(9) . ?
C41 H41 0.9500 . ?
C42 C43 1.371(10) . ?
C42 H42 0.9500 . ?
C43 C44 1.366(10) . ?
C43 H43 0.9500 . ?
C44 C45 1.385(9) . ?
C44 H44 0.9500 . ?
C45 H45 0.9500 . ?
C46 C47 1.531(8) . ?
C46 H46A 0.9900 . ?
C46 H46B 0.9900 . ?
C47 C48 1.517(8) . ?
C47 H47A 0.9900 . ?
C47 H47B 0.9900 . ?
C48 C49 1.528(8) . ?
C48 H48A 0.9900 . ?
C48 H48B 0.9900 . ?
C49 H49A 0.9800 . ?
C49 H49B 0.9800 . ?
C49 H49C 0.9800 . ?
C50 H50A 0.9800 . ?
C50 H50B 0.9800 . ?
C50 H50C 0.9800 . ?
C51 H51A 0.9800 . ?
C51 H51B 0.9800 . ?
C51 H51C 0.9800 . ?
C52 H52A 0.9800 . ?
C52 H52B 0.9800 . ?
C52 H52C 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 109.0(4) . . ?
C1 N1 C13 121.1(4) . . ?
C8 N1 C13 130.0(4) . . ?
C27 N2 C34 108.3(4) . . ?
C27 N2 C39 120.0(4) . . ?
C34 N2 C39 127.3(4) . . ?
N1 C1 C2 127.0(5) . . ?
N1 C1 C6 109.5(5) . . ?
C2 C1 C6 123.4(5) . . ?
C1 C2 C3 116.5(6) . . ?
C1 C2 H2 121.8 . . ?
C3 C2 H2 121.8 . . ?
C4 C3 C2 121.2(6) . . ?
C4 C3 H3 119.4 . . ?
C2 C3 H3 119.4 . . ?
C3 C4 C5 121.4(6) . . ?
C3 C4 H4 119.3 . . ?
C5 C4 H4 119.3 . . ?
C4 C5 C6 118.9(6) . . ?
C4 C5 H5 120.6 . . ?
C6 C5 H5 120.6 . . ?
C5 C6 C1 118.5(5) . . ?
C5 C6 C7 135.1(5) . . ?
C1 C6 C7 106.3(5) . . ?
C12 C7 C8 120.5(5) . . ?
C12 C7 C6 132.5(5) . . ?
C8 C7 C6 107.1(5) . . ?
N1 C8 C9 130.5(5) . . ?
N1 C8 C7 108.0(5) . . ?
C9 C8 C7 121.5(5) . . ?
C10 C9 C8 116.4(5) . . ?
C10 C9 C20 120.8(5) . . ?
C8 C9 C20 122.7(5) . . ?
C9 C10 C11 122.6(5) . . ?
C9 C10 C24 119.8(5) . . ?
C11 C10 C24 117.6(5) . . ?
C12 C11 C10 119.8(5) . . ?
C12 C11 C25 121.5(5) . . ?
C10 C11 C25 118.7(5) . . ?
C11 C12 C7 119.0(5) . . ?
C11 C12 C26 122.9(5) . . ?
C7 C12 C26 118.1(5) . . ?
N1 C13 C14 114.0(4) . . ?
N1 C13 H13A 108.8 . . ?
C14 C13 H13A 108.8 . . ?
N1 C13 H13B 108.8 . . ?
C14 C13 H13B 108.8 . . ?
H13A C13 H13B 107.6 . . ?
C15 C14 C19 119.2(5) . . ?
C15 C14 C13 119.4(5) . . ?
C19 C14 C13 121.4(5) . . ?
C16 C15 C14 119.9(6) . . ?
C16 C15 H15 120.1 . . ?
C14 C15 H15 120.1 . . ?
C17 C16 C15 120.3(6) . . ?
C17 C16 H16 119.8 . . ?
C15 C16 H16 119.8 . . ?
C16 C17 C18 120.3(6) . . ?
C16 C17 H17 119.8 . . ?
C18 C17 H17 119.8 . . ?
C17 C18 C19 120.2(6) . . ?
C17 C18 H18 119.9 . . ?
C19 C18 H18 119.9 . . ?
C18 C19 C14 120.1(6) . . ?
C18 C19 H19 120.0 . . ?
C14 C19 H19 120.0 . . ?
C9 C20 C21 115.9(5) . . ?
C9 C20 H20A 108.3 . . ?
C21 C20 H20A 108.3 . . ?
C9 C20 H20B 108.3 . . ?
C21 C20 H20B 108.3 . . ?
H20A C20 H20B 107.4 . . ?
C22 C21 C20 113.5(5) . . ?
C22 C21 H21A 108.9 . . ?
C20 C21 H21A 108.9 . . ?
C22 C21 H21B 108.9 . . ?
C20 C21 H21B 108.9 . . ?
H21A C21 H21B 107.7 . . ?
C21 C22 C23 113.6(5) . . ?
C21 C22 H22A 108.9 . . ?
C23 C22 H22A 108.9 . . ?
C21 C22 H22B 108.9 . . ?
C23 C22 H22B 108.9 . . ?
H22A C22 H22B 107.7 . . ?
C22 C23 H23A 109.5 . . ?
C22 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
C22 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C10 C24 H24A 109.5 . . ?
C10 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
C10 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
C11 C25 H25A 109.5 . . ?
C11 C25 H25B 109.5 . . ?
H25A C25 H25B 109.5 . . ?
C11 C25 H25C 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
C12 C26 H26A 109.5 . . ?
C12 C26 H26B 109.5 . . ?
H26A C26 H26B 109.5 . . ?
C12 C26 H26C 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
N2 C27 C28 127.7(5) . . ?
N2 C27 C32 110.2(5) . . ?
C28 C27 C32 122.1(5) . . ?
C29 C28 C27 118.0(5) . . ?
C29 C28 H28 121.0 . . ?
C27 C28 H28 121.0 . . ?
C30 C29 C28 121.0(6) . . ?
C30 C29 H29 119.5 . . ?
C28 C29 H29 119.5 . . ?
C29 C30 C31 121.4(6) . . ?
C29 C30 H30 119.3 . . ?
C31 C30 H30 119.3 . . ?
C30 C31 C32 119.0(6) . . ?
C30 C31 H31 120.5 . . ?
C32 C31 H31 120.5 . . ?
C31 C32 C27 118.5(5) . . ?
C31 C32 C33 135.6(5) . . ?
C27 C32 C33 105.8(5) . . ?
C38 C33 C34 120.5(5) . . ?
C38 C33 C32 132.7(5) . . ?
C34 C33 C32 106.8(5) . . ?
C35 C34 N2 129.0(5) . . ?
C35 C34 C33 122.1(5) . . ?
N2 C34 C33 108.8(5) . . ?
C36 C35 C34 116.2(5) . . ?
C36 C35 C46 122.4(5) . . ?
C34 C35 C46 121.2(5) . . ?
C35 C36 C37 122.2(5) . . ?
C35 C36 C50 119.5(5) . . ?
C37 C36 C50 118.3(5) . . ?
C38 C37 C36 120.6(5) . . ?
C38 C37 C51 121.8(5) . . ?
C36 C37 C51 117.4(5) . . ?
C37 C38 C33 118.1(5) . . ?
C37 C38 C52 122.1(5) . . ?
C33 C38 C52 119.7(5) . . ?
N2 C39 C40 114.9(4) . . ?
N2 C39 H39A 108.5 . . ?
C40 C39 H39A 108.5 . . ?
N2 C39 H39B 108.5 . . ?
C40 C39 H39B 108.5 . . ?
H39A C39 H39B 107.5 . . ?
C41 C40 C45 118.4(5) . . ?
C41 C40 C39 124.2(5) . . ?
C45 C40 C39 117.4(5) . . ?
C40 C41 C42 120.1(6) . . ?
C40 C41 H41 120.0 . . ?
C42 C41 H41 120.0 . . ?
C43 C42 C41 120.9(6) . . ?
C43 C42 H42 119.5 . . ?
C41 C42 H42 119.5 . . ?
C44 C43 C42 119.1(6) . . ?
C44 C43 H43 120.5 . . ?
C42 C43 H43 120.5 . . ?
C43 C44 C45 121.1(6) . . ?
C43 C44 H44 119.5 . . ?
C45 C44 H44 119.5 . . ?
C44 C45 C40 120.4(6) . . ?
C44 C45 H45 119.8 . . ?
C40 C45 H45 119.8 . . ?
C35 C46 C47 117.1(5) . . ?
C35 C46 H46A 108.0 . . ?
C47 C46 H46A 108.0 . . ?
C35 C46 H46B 108.0 . . ?
C47 C46 H46B 108.0 . . ?
H46A C46 H46B 107.3 . . ?
C48 C47 C46 111.4(5) . . ?
C48 C47 H47A 109.4 . . ?
C46 C47 H47A 109.4 . . ?
C48 C47 H47B 109.4 . . ?
C46 C47 H47B 109.4 . . ?
H47A C47 H47B 108.0 . . ?
C47 C48 C49 113.5(5) . . ?
C47 C48 H48A 108.9 . . ?
C49 C48 H48A 108.9 . . ?
C47 C48 H48B 108.9 . . ?
C49 C48 H48B 108.9 . . ?
H48A C48 H48B 107.7 . . ?
C48 C49 H49A 109.5 . . ?
C48 C49 H49B 109.5 . . ?
H49A C49 H49B 109.5 . . ?
C48 C49 H49C 109.5 . . ?
H49A C49 H49C 109.5 . . ?
H49B C49 H49C 109.5 . . ?
C36 C50 H50A 109.5 . . ?
C36 C50 H50B 109.5 . . ?
H50A C50 H50B 109.5 . . ?
C36 C50 H50C 109.5 . . ?
H50A C50 H50C 109.5 . . ?
H50B C50 H50C 109.5 . . ?
C37 C51 H51A 109.5 . . ?
C37 C51 H51B 109.5 . . ?
H51A C51 H51B 109.5 . . ?
C37 C51 H51C 109.5 . . ?
H51A C51 H51C 109.5 . . ?
H51B C51 H51C 109.5 . . ?
C38 C52 H52A 109.5 . . ?
C38 C52 H52B 109.5 . . ?
H52A C52 H52B 109.5 . . ?
C38 C52 H52C 109.5 . . ?
H52A C52 H52C 109.5 . . ?
H52B C52 H52C 109.5 . . ?

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        25.35
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.572
_refine_diff_density_min         -0.311
_refine_diff_density_rms         0.088
####################################################################### 
# 
# 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_160107_zj_5_042_2
_database_code_depnum_ccdc_archive 'CCDC 1463901'
_audit_update_record             
;
2016-03-11 deposited with the CCDC.
2017-03-15 downloaded from the CCDC.
;
_audit_creation_date             2016-01-08
_audit_creation_method           
;
Olex2 1.2
(compiled 2014.03.20 svn.r2914 for OlexSys, GUI svn.r4816)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C22 H29 N'
_chemical_formula_sum            'C22 H29 N'
_chemical_formula_weight         307.46
_chemical_melting_point          ?
_chemical_oxdiff_formula         'c10 h10 n2 o8 b1'
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 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x+1/2, y+1/2, -z+1/2'
3 '-x, -y, -z'
4 'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   8.7284(14)
_cell_length_b                   10.1708(12)
_cell_length_c                   21.323(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 93.076(16)
_cell_angle_gamma                90.00
_cell_volume                     1890.2(5)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1972
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      29.5006
_cell_measurement_theta_min      3.5508
_exptl_absorpt_coefficient_mu    0.062
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.90801
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.080
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             672
_exptl_crystal_size_max          0.49
_exptl_crystal_size_mid          0.46
_exptl_crystal_size_min          0.4
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0456
_diffrn_reflns_av_unetI/netI     0.0526
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            8165
_diffrn_reflns_theta_full        25.35
_diffrn_reflns_theta_max         25.35
_diffrn_reflns_theta_min         3.56
_diffrn_ambient_temperature      293.15
_diffrn_detector_area_resol_mean 10.3592
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini ultra'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0149441000
_diffrn_orient_matrix_UB_12      -0.0056173000
_diffrn_orient_matrix_UB_13      -0.0329130000
_diffrn_orient_matrix_UB_21      -0.0717416000
_diffrn_orient_matrix_UB_22      0.0316987000
_diffrn_orient_matrix_UB_23      0.0025985000
_diffrn_orient_matrix_UB_31      0.0354274000
_diffrn_orient_matrix_UB_32      0.0618530000
_diffrn_orient_matrix_UB_33      -0.0044387000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                2283
_reflns_number_total             3454
_reflns_odcompleteness_completeness 99.49
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.184
_refine_diff_density_min         -0.164
_refine_diff_density_rms         0.042
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     213
_refine_ls_number_reflns         3454
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0955
_refine_ls_R_factor_gt           0.0644
_refine_ls_restrained_S_all      1.031
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0890P)²+0.2697P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1609
_refine_ls_wR_factor_ref         0.1857
_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. 
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C13(H13A,H13B), C15(H15A,H15B), C16(H16A,H16B), C17(H17A,H17B), C19(H19A,H19B)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5)
2.c Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C), C18(H18A,H18B,H18C), C20(H20A,H20B,H20C), C21(H21A,H21B,
 H21C), C22(H22A,H22B,H22C)
;
_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_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_refinement_flags_posn
N1 N -0.11158(19) 0.68303(16) 0.25813(9) 0.0500(5) Uani 1 d . . .
C1 C -0.1495(2) 0.7022(2) 0.19516(11) 0.0521(6) Uani 1 d . . .
C2 C -0.2385(3) 0.6217(3) 0.15454(13) 0.0675(7) Uani 1 d . . .
H2 H -0.2774 0.5423 0.1683 0.081 Uiso 1 calc . . R
C3 C -0.2667(4) 0.6626(3) 0.09419(15) 0.0838(9) Uani 1 d . . .
H3 H -0.3260 0.6106 0.0665 0.101 Uiso 1 calc . . R
C4 C -0.2079(4) 0.7813(3) 0.07341(13) 0.0846(9) Uani 1 d . . .
H4 H -0.2292 0.8077 0.0321 0.101 Uiso 1 calc . . R
C5 C -0.1188(3) 0.8600(3) 0.11310(11) 0.0643(7) Uani 1 d . . .
H5 H -0.0787 0.9383 0.0985 0.077 Uiso 1 calc . . R
C6 C -0.0887(2) 0.8221(2) 0.17537(10) 0.0483(5) Uani 1 d . . .
C7 C -0.0070(2) 0.87907(19) 0.23010(10) 0.0442(5) Uani 1 d . . .
C8 C -0.0233(2) 0.79021(18) 0.28046(10) 0.0430(5) Uani 1 d . . .
C9 C 0.0400(2) 0.8167(2) 0.34095(10) 0.0476(5) Uani 1 d . . .
C10 C 0.1189(2) 0.9366(2) 0.34954(11) 0.0511(6) Uani 1 d . . .
C11 C 0.1359(2) 1.0255(2) 0.29911(11) 0.0505(6) Uani 1 d . . .
C12 C 0.0746(2) 0.9969(2) 0.23939(10) 0.0473(5) Uani 1 d . . .
C13 C -0.1490(3) 0.5597(2) 0.28841(13) 0.0617(7) Uani 1 d . . .
H13A H -0.2472 0.5288 0.2708 0.074 Uiso 1 calc . . R
H13B H -0.1595 0.5758 0.3328 0.074 Uiso 1 calc . . R
C14 C -0.0308(3) 0.4532(2) 0.28119(17) 0.0919(10) Uani 1 d . . .
H14A H -0.0255 0.4314 0.2375 0.138 Uiso 1 calc . . GR
H14B H -0.0594 0.3766 0.3041 0.138 Uiso 1 calc . . GR
H14C H 0.0676 0.4839 0.2973 0.138 Uiso 1 calc . . GR
C15 C 0.0217(3) 0.7256(2) 0.39598(11) 0.0590(6) Uani 1 d . . .
H15A H 0.1073 0.7387 0.4263 0.071 Uiso 1 calc . . R
H15B H 0.0256 0.6355 0.3814 0.071 Uiso 1 calc . . R
C16 C -0.1280(3) 0.7462(3) 0.42881(12) 0.0681(7) Uani 1 d . . .
H16A H -0.1292 0.8347 0.4458 0.082 Uiso 1 calc . . R
H16B H -0.2135 0.7384 0.3981 0.082 Uiso 1 calc . . R
C17 C -0.1493(4) 0.6497(3) 0.48097(14) 0.0942(10) Uani 1 d . . .
H17A H -0.0690 0.6635 0.5135 0.113 Uiso 1 calc . . R
H17B H -0.1376 0.5614 0.4647 0.113 Uiso 1 calc . . R
C18 C -0.3033(5) 0.6598(4) 0.51001(17) 0.1240(14) Uani 1 d . . .
H18A H -0.3834 0.6390 0.4790 0.186 Uiso 1 calc . . GR
H18B H -0.3175 0.7476 0.5251 0.186 Uiso 1 calc . . GR
H18C H -0.3067 0.5990 0.5444 0.186 Uiso 1 calc . . GR
C19 C 0.1894(3) 0.9713(3) 0.41381(12) 0.0728(7) Uani 1 d . . .
H19A H 0.1304 0.9297 0.4456 0.087 Uiso 1 calc . . R
H19B H 0.1833 1.0656 0.4197 0.087 Uiso 1 calc . . R
C20 C 0.3570(3) 0.9282(4) 0.42288(15) 0.1054(11) Uani 1 d . . .
H20A H 0.4163 0.9698 0.3918 0.158 Uiso 1 calc . . GR
H20B H 0.3635 0.8344 0.4184 0.158 Uiso 1 calc . . GR
H20C H 0.3965 0.9532 0.4641 0.158 Uiso 1 calc . . GR
C21 C 0.2209(3) 1.1539(2) 0.31163(14) 0.0752(8) Uani 1 d . . .
H21A H 0.2260 1.2021 0.2731 0.113 Uiso 1 calc . . GR
H21B H 0.3230 1.1356 0.3284 0.113 Uiso 1 calc . . GR
H21C H 0.1676 1.2052 0.3413 0.113 Uiso 1 calc . . GR
C22 C 0.0892(3) 1.0895(2) 0.18438(12) 0.0708(7) Uani 1 d . . .
H22A H 0.1257 1.0418 0.1493 0.106 Uiso 1 calc . . GR
H22B H 0.1604 1.1584 0.1960 0.106 Uiso 1 calc . . GR
H22C H -0.0092 1.1271 0.1729 0.106 Uiso 1 calc . . GR


_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 1.379(3) . ?
N1 C8 1.403(2) . ?
N1 C13 1.456(3) . ?
C1 C2 1.397(3) . ?
C1 C6 1.403(3) . ?
C2 H2 0.9300 . ?
C2 C3 1.362(4) . ?
C3 H3 0.9300 . ?
C3 C4 1.393(4) . ?
C4 H4 0.9300 . ?
C4 C5 1.376(4) . ?
C5 H5 0.9300 . ?
C5 C6 1.394(3) . ?
C6 C7 1.455(3) . ?
C7 C8 1.416(3) . ?
C7 C12 1.402(3) . ?
C8 C9 1.402(3) . ?
C9 C10 1.407(3) . ?
C9 C15 1.510(3) . ?
C10 C11 1.419(3) . ?
C10 C19 1.513(3) . ?
C11 C12 1.385(3) . ?
C11 C21 1.519(3) . ?
C12 C22 1.515(3) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C13 C14 1.509(4) . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C15 C16 1.529(3) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C16 C17 1.503(4) . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C17 C18 1.513(4) . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C19 H19A 0.9700 . ?
C19 H19B 0.9700 . ?
C19 C20 1.530(4) . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 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
C1 N1 C8 108.60(16) . . ?
C1 N1 C13 120.39(18) . . ?
C8 N1 C13 130.61(19) . . ?
N1 C1 C2 128.1(2) . . ?
N1 C1 C6 109.92(18) . . ?
C2 C1 C6 122.0(2) . . ?
C1 C2 H2 120.9 . . ?
C3 C2 C1 118.2(3) . . ?
C3 C2 H2 120.9 . . ?
C2 C3 H3 119.5 . . ?
C2 C3 C4 120.9(3) . . ?
C4 C3 H3 119.5 . . ?
C3 C4 H4 119.5 . . ?
C5 C4 C3 121.0(3) . . ?
C5 C4 H4 119.5 . . ?
C4 C5 H5 120.1 . . ?
C4 C5 C6 119.7(3) . . ?
C6 C5 H5 120.1 . . ?
C1 C6 C7 106.37(18) . . ?
C5 C6 C1 118.2(2) . . ?
C5 C6 C7 135.5(2) . . ?
C8 C7 C6 106.80(18) . . ?
C12 C7 C6 132.6(2) . . ?
C12 C7 C8 120.59(19) . . ?
N1 C8 C7 108.31(18) . . ?
C9 C8 N1 130.06(18) . . ?
C9 C8 C7 121.61(18) . . ?
C8 C9 C10 116.89(19) . . ?
C8 C9 C15 122.96(19) . . ?
C10 C9 C15 120.1(2) . . ?
C9 C10 C11 121.6(2) . . ?
C9 C10 C19 119.5(2) . . ?
C11 C10 C19 118.9(2) . . ?
C10 C11 C21 119.0(2) . . ?
C12 C11 C10 120.78(19) . . ?
C12 C11 C21 120.2(2) . . ?
C7 C12 C22 119.0(2) . . ?
C11 C12 C7 118.52(19) . . ?
C11 C12 C22 122.4(2) . . ?
N1 C13 H13A 108.8 . . ?
N1 C13 H13B 108.8 . . ?
N1 C13 C14 113.7(2) . . ?
H13A C13 H13B 107.7 . . ?
C14 C13 H13A 108.8 . . ?
C14 C13 H13B 108.8 . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C9 C15 H15A 108.8 . . ?
C9 C15 H15B 108.8 . . ?
C9 C15 C16 113.63(19) . . ?
H15A C15 H15B 107.7 . . ?
C16 C15 H15A 108.8 . . ?
C16 C15 H15B 108.8 . . ?
C15 C16 H16A 109.0 . . ?
C15 C16 H16B 109.0 . . ?
H16A C16 H16B 107.8 . . ?
C17 C16 C15 113.1(2) . . ?
C17 C16 H16A 109.0 . . ?
C17 C16 H16B 109.0 . . ?
C16 C17 H17A 108.8 . . ?
C16 C17 H17B 108.8 . . ?
C16 C17 C18 114.0(3) . . ?
H17A C17 H17B 107.6 . . ?
C18 C17 H17A 108.8 . . ?
C18 C17 H17B 108.8 . . ?
C17 C18 H18A 109.5 . . ?
C17 C18 H18B 109.5 . . ?
C17 C18 H18C 109.5 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C10 C19 H19A 109.0 . . ?
C10 C19 H19B 109.0 . . ?
C10 C19 C20 112.8(2) . . ?
H19A C19 H19B 107.8 . . ?
C20 C19 H19A 109.0 . . ?
C20 C19 H19B 109.0 . . ?
C19 C20 H20A 109.5 . . ?
C19 C20 H20B 109.5 . . ?
C19 C20 H20C 109.5 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C11 C21 H21A 109.5 . . ?
C11 C21 H21B 109.5 . . ?
C11 C21 H21C 109.5 . . ?
H21A C21 H21B 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C12 C22 H22A 109.5 . . ?
C12 C22 H22B 109.5 . . ?
C12 C22 H22C 109.5 . . ?
H22A C22 H22B 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 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
N1 C1 C2 C3 177.4(2) . . . . ?
N1 C1 C6 C5 -178.38(18) . . . . ?
N1 C1 C6 C7 0.5(2) . . . . ?
N1 C8 C9 C10 -177.48(19) . . . . ?
N1 C8 C9 C15 0.2(3) . . . . ?
C1 N1 C8 C7 0.5(2) . . . . ?
C1 N1 C8 C9 179.0(2) . . . . ?
C1 N1 C13 C14 84.8(3) . . . . ?
C1 C2 C3 C4 0.3(4) . . . . ?
C1 C6 C7 C8 -0.2(2) . . . . ?
C1 C6 C7 C12 -179.2(2) . . . . ?
C2 C1 C6 C5 -0.2(3) . . . . ?
C2 C1 C6 C7 178.65(19) . . . . ?
C2 C3 C4 C5 0.5(5) . . . . ?
C3 C4 C5 C6 -1.1(4) . . . . ?
C4 C5 C6 C1 1.0(3) . . . . ?
C4 C5 C6 C7 -177.5(2) . . . . ?
C5 C6 C7 C8 178.4(2) . . . . ?
C5 C6 C7 C12 -0.7(4) . . . . ?
C6 C1 C2 C3 -0.4(4) . . . . ?
C6 C7 C8 N1 -0.2(2) . . . . ?
C6 C7 C8 C9 -178.84(17) . . . . ?
C6 C7 C12 C11 177.6(2) . . . . ?
C6 C7 C12 C22 -0.9(3) . . . . ?
C7 C8 C9 C10 0.8(3) . . . . ?
C7 C8 C9 C15 178.52(19) . . . . ?
C8 N1 C1 C2 -178.6(2) . . . . ?
C8 N1 C1 C6 -0.6(2) . . . . ?
C8 N1 C13 C14 -87.1(3) . . . . ?
C8 C7 C12 C11 -1.3(3) . . . . ?
C8 C7 C12 C22 -179.87(19) . . . . ?
C8 C9 C10 C11 -1.1(3) . . . . ?
C8 C9 C10 C19 179.72(19) . . . . ?
C8 C9 C15 C16 -84.4(3) . . . . ?
C9 C10 C11 C12 0.1(3) . . . . ?
C9 C10 C11 C21 179.4(2) . . . . ?
C9 C10 C19 C20 92.5(3) . . . . ?
C9 C15 C16 C17 176.5(2) . . . . ?
C10 C9 C15 C16 93.2(3) . . . . ?
C10 C11 C12 C7 1.1(3) . . . . ?
C10 C11 C12 C22 179.6(2) . . . . ?
C11 C10 C19 C20 -86.7(3) . . . . ?
C12 C7 C8 N1 179.00(17) . . . . ?
C12 C7 C8 C9 0.4(3) . . . . ?
C13 N1 C1 C2 7.9(3) . . . . ?
C13 N1 C1 C6 -174.11(18) . . . . ?
C13 N1 C8 C7 173.1(2) . . . . ?
C13 N1 C8 C9 -8.4(3) . . . . ?
C15 C9 C10 C11 -178.82(19) . . . . ?
C15 C9 C10 C19 2.0(3) . . . . ?
C15 C16 C17 C18 -174.4(3) . . . . ?
C19 C10 C11 C12 179.3(2) . . . . ?
C19 C10 C11 C21 -1.4(3) . . . . ?
C21 C11 C12 C7 -178.2(2) . . . . ?
C21 C11 C12 C22 0.3(3) . . . . ?

