# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2022

####################################################################### 
# 
# 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_C12NNp
_database_code_depnum_ccdc_archive 'CCDC 2202293'
loop_
_audit_author_name
_audit_author_address
'Wataru Setaka'
;Tokyo Metropolitan University
Japan
;
_audit_update_record             
;
2022-08-19 deposited with the CCDC.	2022-10-14 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        C12Np
_chemical_name_common            C12NNp
_chemical_melting_point          '382.3-383.8 K'
_chemical_formula_moiety         'C34 H54 N2'
_chemical_formula_sum            'C34 H54 N2'
_chemical_formula_weight         490.79

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_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+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   10.7668(3)
_cell_length_b                   18.0397(5)
_cell_length_c                   15.5823(5)
_cell_angle_alpha                90
_cell_angle_beta                 93.8990(10)
_cell_angle_gamma                90
_cell_volume                     3019.54(15)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9944
_cell_measurement_theta_min      3.74
_cell_measurement_theta_max      74.50

_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.080
_exptl_crystal_F_000             1088
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.420
_exptl_crystal_size_mid          0.400
_exptl_crystal_size_min          0.280
_exptl_absorpt_coefficient_mu    0.455
_shelx_estimated_absorpt_T_min   0.839
_shelx_estimated_absorpt_T_max   0.914
_exptl_absorpt_correction_type   Multi-Scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 - Bruker AXS area detector scaling and absorption correction
;
_exptl_absorpt_correction_T_min  0.931
_exptl_absorpt_correction_T_max  0.938

_exptl_special_details           
;
;

_diffrn_ambient_temperature      100(2)
_diffrn_source                   'sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_monochromator  'multilayered conforcal mirror'
_diffrn_measurement_device_type  'Bruker D8 goniometer'
_diffrn_measurement_method       'omega scans'
_diffrn_detector_area_resol_mean 7.3910
_diffrn_reflns_number            24260
_diffrn_reflns_av_unetI/netI     0.0233
_diffrn_reflns_av_R_equivalents  0.0229
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         3.753
_diffrn_reflns_theta_max         75.508
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.966
_diffrn_measured_fraction_theta_full 0.978
_diffrn_reflns_Laue_measured_fraction_max 0.966
_diffrn_reflns_Laue_measured_fraction_full 0.978
_diffrn_reflns_point_group_measured_fraction_max 0.966
_diffrn_reflns_point_group_measured_fraction_full 0.978
_reflns_number_total             6066
_reflns_number_gt                5852
_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       'APEX3 v2019.1-0 (Bruker AXS)'
_computing_cell_refinement       'APEX3 v2019.1-0 (Bruker AXS)'
_computing_data_reduction        'SAINT V8.40A (Bruker Nano, Inc., 2019)'
_computing_structure_solution    'Sir-2019 (IUCr, 2019)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 2020)'
_computing_publication_material  'WinGX (Farrugia, 2020)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0500P)²+0.7915P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_extinction_coef       0.0058(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         6066
_refine_ls_number_parameters     326
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0413
_refine_ls_R_factor_gt           0.0404
_refine_ls_wR_factor_ref         0.1062
_refine_ls_wR_factor_gt          0.1057
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_restrained_S_all      1.030
_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 0.33657(7) 0.17529(5) 0.13394(5) 0.02669(18) Uani 1 1 d . . . . .
N2 N 0.82758(7) 0.11707(5) 0.03661(5) 0.02843(19) Uani 1 1 d . . . . .
C1 C 0.45819(9) 0.15875(5) 0.10911(6) 0.0247(2) Uani 1 1 d . . . . .
C2 C 0.49915(9) 0.08806(5) 0.09591(6) 0.0282(2) Uani 1 1 d . . . . .
H2 H 0.444346 0.047556 0.102875 0.034 Uiso 1 1 calc R U . . .
C3 C 0.62056(9) 0.07426(5) 0.07229(6) 0.0287(2) Uani 1 1 d . . . . .
H3 H 0.646503 0.024496 0.064690 0.034 Uiso 1 1 calc R U . . .
C4 C 0.70225(9) 0.13049(5) 0.05997(6) 0.0256(2) Uani 1 1 d . . . . .
C5 C 0.66260(9) 0.20478(5) 0.07019(6) 0.0245(2) Uani 1 1 d . . . . .
C6 C 0.74110(9) 0.26535(6) 0.05420(7) 0.0306(2) Uani 1 1 d . . . . .
H6 H 0.822321 0.256382 0.036250 0.037 Uiso 1 1 calc R U . . .
C7 C 0.70186(10) 0.33629(6) 0.06419(7) 0.0345(2) Uani 1 1 d . . . . .
H7 H 0.754373 0.376441 0.050992 0.041 Uiso 1 1 calc R U . . .
C8 C 0.58412(10) 0.35033(6) 0.09392(7) 0.0325(2) Uani 1 1 d . . . . .
H8 H 0.558299 0.399995 0.102423 0.039 Uiso 1 1 calc R U . . .
C9 C 0.50661(9) 0.29340(5) 0.11067(6) 0.0277(2) Uani 1 1 d . . . . .
H9 H 0.427908 0.303807 0.132032 0.033 Uiso 1 1 calc R U . . .
C10 C 0.54119(8) 0.21899(5) 0.09684(6) 0.0238(2) Uani 1 1 d . . . . .
C11 C 0.27364(9) 0.11898(6) 0.18308(7) 0.0328(2) Uani 1 1 d . . . . .
H11A H 0.256226 0.075375 0.145591 0.039 Uiso 1 1 calc R U . . .
H11B H 0.192642 0.139177 0.198542 0.039 Uiso 1 1 calc R U . . .
C12 C 0.34590(10) 0.09336(6) 0.26467(7) 0.0341(2) Uani 1 1 d . . . . .
H12A H 0.294197 0.057206 0.294089 0.041 Uiso 1 1 calc R U . . .
H12B H 0.421535 0.067041 0.248473 0.041 Uiso 1 1 calc R U . . .
C13 C 0.38493(11) 0.15416(6) 0.32780(8) 0.0373(2) Uani 1 1 d . . . . .
H13A H 0.309627 0.176910 0.349717 0.045 Uiso 1 1 calc R U . . .
H13B H 0.429634 0.193131 0.297486 0.045 Uiso 1 1 calc R U . . .
C14 C 0.46901(11) 0.12566(7) 0.40391(7) 0.0389(3) Uani 1 1 d . . . . .
H14A H 0.481298 0.165692 0.447107 0.047 Uiso 1 1 calc R U . . .
H14B H 0.427061 0.083889 0.431293 0.047 Uiso 1 1 calc R U . . .
C15 C 0.59531(11) 0.09988(7) 0.37754(7) 0.0410(3) Uani 1 1 d . . . . .
H15A H 0.631468 0.139406 0.342899 0.049 Uiso 1 1 calc R U . . .
H15B H 0.583069 0.055672 0.340273 0.049 Uiso 1 1 calc R U . . .
C16 C 0.68818(12) 0.08062(7) 0.45228(8) 0.0426(3) Uani 1 1 d . . . . .
H16A H 0.653652 0.040097 0.486278 0.051 Uiso 1 1 calc R U . . .
H16B H 0.699987 0.124379 0.490303 0.051 Uiso 1 1 calc R U . . .
C17 C 0.81427(11) 0.05662(7) 0.42262(8) 0.0421(3) Uani 1 1 d . . . . .
H17A H 0.863047 0.033475 0.471685 0.051 Uiso 1 1 calc R U . . .
H17B H 0.800673 0.018504 0.377250 0.051 Uiso 1 1 calc R U . . .
C18 C 0.88988(11) 0.11961(6) 0.38787(7) 0.0372(2) Uani 1 1 d . . . . .
H18A H 0.916895 0.152906 0.436082 0.045 Uiso 1 1 calc R U . . .
H18B H 0.835535 0.148647 0.346552 0.045 Uiso 1 1 calc R U . . .
C19 C 1.00435(10) 0.09464(7) 0.34327(8) 0.0388(3) Uani 1 1 d . . . . .
H19A H 1.052746 0.060009 0.381819 0.047 Uiso 1 1 calc R U . . .
H19B H 1.057432 0.138459 0.334622 0.047 Uiso 1 1 calc R U . . .
C20 C 0.97627(10) 0.05668(6) 0.25645(7) 0.0338(2) Uani 1 1 d . . . . .
H20A H 1.055650 0.040163 0.234162 0.041 Uiso 1 1 calc R U . . .
H20B H 0.925244 0.011993 0.265147 0.041 Uiso 1 1 calc R U . . .
C21 C 0.90811(10) 0.10575(6) 0.18935(7) 0.0347(2) Uani 1 1 d . . . . .
H21A H 0.823380 0.116059 0.207327 0.042 Uiso 1 1 calc R U . . .
H21B H 0.952548 0.153645 0.186603 0.042 Uiso 1 1 calc R U . . .
C22 C 0.89802(9) 0.07100(6) 0.10043(7) 0.0308(2) Uani 1 1 d . . . . .
H22A H 0.982761 0.062724 0.081342 0.037 Uiso 1 1 calc R U . . .
H22B H 0.856838 0.022108 0.103638 0.037 Uiso 1 1 calc R U . . .
C23 C 0.82950(10) 0.08578(6) -0.05034(7) 0.0318(2) Uani 1 1 d . . . . .
H23A H 0.781952 0.038768 -0.052957 0.038 Uiso 1 1 calc R U . . .
H23B H 0.916550 0.074292 -0.062341 0.038 Uiso 1 1 calc R U . . .
C24 C 0.77448(11) 0.13797(6) -0.11879(7) 0.0341(2) Uani 1 1 d . . . . .
H24A H 0.829745 0.181583 -0.122155 0.041 Uiso 1 1 calc R U . . .
H24B H 0.692802 0.155779 -0.101626 0.041 Uiso 1 1 calc R U . . .
C25 C 0.75701(10) 0.10264(6) -0.20711(7) 0.0355(2) Uani 1 1 d . . . . .
H25A H 0.702555 0.058688 -0.203428 0.043 Uiso 1 1 calc R U . . .
H25B H 0.838888 0.085207 -0.224314 0.043 Uiso 1 1 calc R U . . .
C26 C 0.70045(11) 0.15434(7) -0.27670(7) 0.0396(3) Uani 1 1 d . . . . .
H26A H 0.760042 0.195032 -0.285256 0.048 Uiso 1 1 calc R U . . .
H26B H 0.689644 0.126375 -0.331369 0.048 Uiso 1 1 calc R U . . .
C27 C 0.57574(10) 0.18809(6) -0.25766(8) 0.0374(2) Uani 1 1 d . . . . .
H27A H 0.588197 0.219359 -0.205575 0.045 Uiso 1 1 calc R U . . .
H27B H 0.548024 0.221008 -0.306074 0.045 Uiso 1 1 calc R U . . .
C28 C 0.47261(11) 0.13310(6) -0.24377(8) 0.0382(3) Uani 1 1 d . . . . .
H28A H 0.452979 0.105398 -0.297845 0.046 Uiso 1 1 calc R U . . .
H28B H 0.502464 0.096976 -0.199199 0.046 Uiso 1 1 calc R U . . .
C29 C 0.35485(10) 0.16952(6) -0.21629(7) 0.0347(2) Uani 1 1 d . . . . .
H29A H 0.324789 0.205546 -0.260918 0.042 Uiso 1 1 calc R U . . .
H29B H 0.374427 0.197299 -0.162262 0.042 Uiso 1 1 calc R U . . .
C30 C 0.25217(10) 0.11430(6) -0.20230(7) 0.0338(2) Uani 1 1 d . . . . .
H30A H 0.284968 0.076464 -0.160676 0.041 Uiso 1 1 calc R U . . .
H30B H 0.230149 0.088671 -0.257432 0.041 Uiso 1 1 calc R U . . .
C31 C 0.13413(10) 0.14699(7) -0.16952(7) 0.0359(2) Uani 1 1 d . . . . .
H31A H 0.075461 0.106049 -0.159871 0.043 Uiso 1 1 calc R U . . .
H31B H 0.094624 0.179413 -0.214804 0.043 Uiso 1 1 calc R U . . .
C32 C 0.15348(10) 0.19175(6) -0.08663(7) 0.0344(2) Uani 1 1 d . . . . .
H32A H 0.198704 0.237841 -0.099248 0.041 Uiso 1 1 calc R U . . .
H32B H 0.070913 0.206248 -0.067804 0.041 Uiso 1 1 calc R U . . .
C33 C 0.22479(10) 0.15198(6) -0.01261(7) 0.0320(2) Uani 1 1 d . . . . .
H33A H 0.303265 0.131754 -0.032624 0.038 Uiso 1 1 calc R U . . .
H33B H 0.174482 0.109952 0.006637 0.038 Uiso 1 1 calc R U . . .
C34 C 0.25438(9) 0.20435(6) 0.06253(7) 0.0297(2) Uani 1 1 d . . . . .
H34A H 0.293282 0.249513 0.040204 0.036 Uiso 1 1 calc R U . . .
H34B H 0.174923 0.219500 0.085780 0.036 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 C1 1.4220(12) . ?
N1 C11 1.4656(13) . ?
N1 C34 1.4703(12) . ?
N2 C4 1.4418(12) . ?
N2 C22 1.4670(13) . ?
N2 C23 1.4693(13) . ?
C1 C2 1.3695(14) . ?
C1 C10 1.4279(13) . ?
C2 C3 1.4041(14) . ?
C2 H2 0.9500 . ?
C3 C4 1.3648(14) . ?
C3 H3 0.9500 . ?
C4 C5 1.4187(13) . ?
C5 C6 1.4138(14) . ?
C5 C10 1.4216(13) . ?
C6 C7 1.3598(15) . ?
C6 H6 0.9500 . ?
C7 C8 1.4020(15) . ?
C7 H7 0.9500 . ?
C8 C9 1.3598(14) . ?
C8 H8 0.9500 . ?
C9 C10 1.4134(13) . ?
C9 H9 0.9500 . ?
C11 C12 1.5168(15) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 C13 1.5136(15) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 C14 1.5311(16) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C14 C15 1.5199(16) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C15 C16 1.5226(17) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C16 C17 1.5262(17) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C17 C18 1.5187(17) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C18 C19 1.5236(16) . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C19 C20 1.5282(16) . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
C20 C21 1.5202(15) . ?
C20 H20A 0.9900 . ?
C20 H20B 0.9900 . ?
C21 C22 1.5179(15) . ?
C21 H21A 0.9900 . ?
C21 H21B 0.9900 . ?
C22 H22A 0.9900 . ?
C22 H22B 0.9900 . ?
C23 C24 1.5130(15) . ?
C23 H23A 0.9900 . ?
C23 H23B 0.9900 . ?
C24 C25 1.5167(15) . ?
C24 H24A 0.9900 . ?
C24 H24B 0.9900 . ?
C25 C26 1.5254(16) . ?
C25 H25A 0.9900 . ?
C25 H25B 0.9900 . ?
C26 C27 1.5218(16) . ?
C26 H26A 0.9900 . ?
C26 H26B 0.9900 . ?
C27 C28 1.5154(15) . ?
C27 H27A 0.9900 . ?
C27 H27B 0.9900 . ?
C28 C29 1.5155(15) . ?
C28 H28A 0.9900 . ?
C28 H28B 0.9900 . ?
C29 C30 1.5149(15) . ?
C29 H29A 0.9900 . ?
C29 H29B 0.9900 . ?
C30 C31 1.5206(15) . ?
C30 H30A 0.9900 . ?
C30 H30B 0.9900 . ?
C31 C32 1.5255(15) . ?
C31 H31A 0.9900 . ?
C31 H31B 0.9900 . ?
C32 C33 1.5212(14) . ?
C32 H32A 0.9900 . ?
C32 H32B 0.9900 . ?
C33 C34 1.5213(14) . ?
C33 H33A 0.9900 . ?
C33 H33B 0.9900 . ?
C34 H34A 0.9900 . ?
C34 H34B 0.9900 . ?

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 C11 117.62(8) . . ?
C1 N1 C34 112.76(7) . . ?
C11 N1 C34 111.51(8) . . ?
C4 N2 C22 111.94(8) . . ?
C4 N2 C23 111.68(8) . . ?
C22 N2 C23 111.61(8) . . ?
C2 C1 N1 123.24(9) . . ?
C2 C1 C10 118.53(8) . . ?
N1 C1 C10 118.23(8) . . ?
C1 C2 C3 121.30(9) . . ?
C1 C2 H2 119.4 . . ?
C3 C2 H2 119.4 . . ?
C4 C3 C2 121.70(9) . . ?
C4 C3 H3 119.1 . . ?
C2 C3 H3 119.1 . . ?
C3 C4 C5 118.99(9) . . ?
C3 C4 N2 122.27(9) . . ?
C5 C4 N2 118.74(8) . . ?
C6 C5 C4 121.48(9) . . ?
C6 C5 C10 119.00(9) . . ?
C4 C5 C10 119.52(8) . . ?
C7 C6 C5 120.86(9) . . ?
C7 C6 H6 119.6 . . ?
C5 C6 H6 119.6 . . ?
C6 C7 C8 120.19(10) . . ?
C6 C7 H7 119.9 . . ?
C8 C7 H7 119.9 . . ?
C9 C8 C7 120.49(9) . . ?
C9 C8 H8 119.8 . . ?
C7 C8 H8 119.8 . . ?
C8 C9 C10 121.11(9) . . ?
C8 C9 H9 119.4 . . ?
C10 C9 H9 119.4 . . ?
C9 C10 C5 118.21(9) . . ?
C9 C10 C1 121.91(9) . . ?
C5 C10 C1 119.88(8) . . ?
N1 C11 C12 114.84(8) . . ?
N1 C11 H11A 108.6 . . ?
C12 C11 H11A 108.6 . . ?
N1 C11 H11B 108.6 . . ?
C12 C11 H11B 108.6 . . ?
H11A C11 H11B 107.5 . . ?
C13 C12 C11 115.33(9) . . ?
C13 C12 H12A 108.4 . . ?
C11 C12 H12A 108.4 . . ?
C13 C12 H12B 108.4 . . ?
C11 C12 H12B 108.4 . . ?
H12A C12 H12B 107.5 . . ?
C12 C13 C14 112.55(9) . . ?
C12 C13 H13A 109.1 . . ?
C14 C13 H13A 109.1 . . ?
C12 C13 H13B 109.1 . . ?
C14 C13 H13B 109.1 . . ?
H13A C13 H13B 107.8 . . ?
C15 C14 C13 112.71(9) . . ?
C15 C14 H14A 109.0 . . ?
C13 C14 H14A 109.0 . . ?
C15 C14 H14B 109.0 . . ?
C13 C14 H14B 109.0 . . ?
H14A C14 H14B 107.8 . . ?
C14 C15 C16 114.59(10) . . ?
C14 C15 H15A 108.6 . . ?
C16 C15 H15A 108.6 . . ?
C14 C15 H15B 108.6 . . ?
C16 C15 H15B 108.6 . . ?
H15A C15 H15B 107.6 . . ?
C15 C16 C17 112.62(10) . . ?
C15 C16 H16A 109.1 . . ?
C17 C16 H16A 109.1 . . ?
C15 C16 H16B 109.1 . . ?
C17 C16 H16B 109.1 . . ?
H16A C16 H16B 107.8 . . ?
C18 C17 C16 113.90(10) . . ?
C18 C17 H17A 108.8 . . ?
C16 C17 H17A 108.8 . . ?
C18 C17 H17B 108.8 . . ?
C16 C17 H17B 108.8 . . ?
H17A C17 H17B 107.7 . . ?
C17 C18 C19 114.29(10) . . ?
C17 C18 H18A 108.7 . . ?
C19 C18 H18A 108.7 . . ?
C17 C18 H18B 108.7 . . ?
C19 C18 H18B 108.7 . . ?
H18A C18 H18B 107.6 . . ?
C18 C19 C20 114.76(9) . . ?
C18 C19 H19A 108.6 . . ?
C20 C19 H19A 108.6 . . ?
C18 C19 H19B 108.6 . . ?
C20 C19 H19B 108.6 . . ?
H19A C19 H19B 107.6 . . ?
C21 C20 C19 113.90(9) . . ?
C21 C20 H20A 108.8 . . ?
C19 C20 H20A 108.8 . . ?
C21 C20 H20B 108.8 . . ?
C19 C20 H20B 108.8 . . ?
H20A C20 H20B 107.7 . . ?
C22 C21 C20 112.87(9) . . ?
C22 C21 H21A 109.0 . . ?
C20 C21 H21A 109.0 . . ?
C22 C21 H21B 109.0 . . ?
C20 C21 H21B 109.0 . . ?
H21A C21 H21B 107.8 . . ?
N2 C22 C21 112.73(8) . . ?
N2 C22 H22A 109.0 . . ?
C21 C22 H22A 109.0 . . ?
N2 C22 H22B 109.0 . . ?
C21 C22 H22B 109.0 . . ?
H22A C22 H22B 107.8 . . ?
N2 C23 C24 112.43(8) . . ?
N2 C23 H23A 109.1 . . ?
C24 C23 H23A 109.1 . . ?
N2 C23 H23B 109.1 . . ?
C24 C23 H23B 109.1 . . ?
H23A C23 H23B 107.8 . . ?
C23 C24 C25 113.36(9) . . ?
C23 C24 H24A 108.9 . . ?
C25 C24 H24A 108.9 . . ?
C23 C24 H24B 108.9 . . ?
C25 C24 H24B 108.9 . . ?
H24A C24 H24B 107.7 . . ?
C24 C25 C26 114.02(9) . . ?
C24 C25 H25A 108.7 . . ?
C26 C25 H25A 108.7 . . ?
C24 C25 H25B 108.7 . . ?
C26 C25 H25B 108.7 . . ?
H25A C25 H25B 107.6 . . ?
C27 C26 C25 114.89(9) . . ?
C27 C26 H26A 108.5 . . ?
C25 C26 H26A 108.5 . . ?
C27 C26 H26B 108.5 . . ?
C25 C26 H26B 108.5 . . ?
H26A C26 H26B 107.5 . . ?
C28 C27 C26 115.51(10) . . ?
C28 C27 H27A 108.4 . . ?
C26 C27 H27A 108.4 . . ?
C28 C27 H27B 108.4 . . ?
C26 C27 H27B 108.4 . . ?
H27A C27 H27B 107.5 . . ?
C29 C28 C27 113.07(9) . . ?
C29 C28 H28A 109.0 . . ?
C27 C28 H28A 109.0 . . ?
C29 C28 H28B 109.0 . . ?
C27 C28 H28B 109.0 . . ?
H28A C28 H28B 107.8 . . ?
C28 C29 C30 112.85(9) . . ?
C28 C29 H29A 109.0 . . ?
C30 C29 H29A 109.0 . . ?
C28 C29 H29B 109.0 . . ?
C30 C29 H29B 109.0 . . ?
H29A C29 H29B 107.8 . . ?
C29 C30 C31 115.34(9) . . ?
C29 C30 H30A 108.4 . . ?
C31 C30 H30A 108.4 . . ?
C29 C30 H30B 108.4 . . ?
C31 C30 H30B 108.4 . . ?
H30A C30 H30B 107.5 . . ?
C30 C31 C32 114.88(9) . . ?
C30 C31 H31A 108.5 . . ?
C32 C31 H31A 108.5 . . ?
C30 C31 H31B 108.5 . . ?
C32 C31 H31B 108.5 . . ?
H31A C31 H31B 107.5 . . ?
C33 C32 C31 115.15(9) . . ?
C33 C32 H32A 108.5 . . ?
C31 C32 H32A 108.5 . . ?
C33 C32 H32B 108.5 . . ?
C31 C32 H32B 108.5 . . ?
H32A C32 H32B 107.5 . . ?
C32 C33 C34 111.05(9) . . ?
C32 C33 H33A 109.4 . . ?
C34 C33 H33A 109.4 . . ?
C32 C33 H33B 109.4 . . ?
C34 C33 H33B 109.4 . . ?
H33A C33 H33B 108.0 . . ?
N1 C34 C33 116.41(8) . . ?
N1 C34 H34A 108.2 . . ?
C33 C34 H34A 108.2 . . ?
N1 C34 H34B 108.2 . . ?
C33 C34 H34B 108.2 . . ?
H34A C34 H34B 107.3 . . ?

_refine_diff_density_max         0.282
_refine_diff_density_min         -0.192
_refine_diff_density_rms         0.037


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: ethanol'
_chemical_compound_source        no
####################################################################### 
# 
# 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_C14NNp
_database_code_depnum_ccdc_archive 'CCDC 2202294'
loop_
_audit_author_name
_audit_author_address
'Wataru Setaka'
;Tokyo Metropolitan University
Japan
;
_audit_update_record             
;
2022-08-19 deposited with the CCDC.	2022-10-14 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        C14Np
_chemical_name_common            C14NNp
_chemical_melting_point          '325.4-326.3 K'
_chemical_formula_moiety         'C38 H62 N2'
_chemical_formula_sum            'C38 H62 N2'
_chemical_formula_weight         546.89

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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                   11.7462(14)
_cell_length_b                   9.5109(12)
_cell_length_c                   30.593(4)
_cell_angle_alpha                90
_cell_angle_beta                 90.057(6)
_cell_angle_gamma                90
_cell_volume                     3417.8(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    123(2)
_cell_measurement_reflns_used    9785
_cell_measurement_theta_min      3.76
_cell_measurement_theta_max      74.60

_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.063
_exptl_crystal_F_000             1216
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.320
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    0.445
_shelx_estimated_absorpt_T_min   0.871
_shelx_estimated_absorpt_T_max   0.957
_exptl_absorpt_correction_type   Multi-Scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 - Bruker AXS area detector scaling and absorption correction
;
_exptl_absorpt_correction_T_min  0.817
_exptl_absorpt_correction_T_max  0.957

_exptl_special_details           
;
;

_diffrn_ambient_temperature      123(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_radiation_monochromator  'multilayered conforcal mirror'
_diffrn_measurement_device_type  'Bruker D8 goniometer'
_diffrn_measurement_method       'omega scans'
_diffrn_detector_area_resol_mean 7.3910
_diffrn_reflns_number            35956
_diffrn_reflns_av_unetI/netI     0.0621
_diffrn_reflns_av_R_equivalents  0.0648
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -38
_diffrn_reflns_limit_l_max       38
_diffrn_reflns_theta_min         2.889
_diffrn_reflns_theta_max         75.190
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.970
_diffrn_measured_fraction_theta_full 0.981
_diffrn_reflns_Laue_measured_fraction_max 0.970
_diffrn_reflns_Laue_measured_fraction_full 0.981
_diffrn_reflns_point_group_measured_fraction_max 0.970
_diffrn_reflns_point_group_measured_fraction_full 0.981
_reflns_number_total             6841
_reflns_number_gt                6068
_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       'APEX3 v2019.1-0 (Bruker AXS)'
_computing_cell_refinement       'APEX3 v2019.1-0 (Bruker AXS)'
_computing_data_reduction        'SAINT V8.40A (Bruker Nano, Inc., 2019)'
_computing_structure_solution    'Sir-2019 (IUCr, 2019)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 2020)'
_computing_publication_material  'WinGX (Farrugia, 2020)'


_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0486P)²+10.8251P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_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         6841
_refine_ls_number_parameters     380
_refine_ls_number_restraints     29
_refine_ls_R_factor_all          0.1059
_refine_ls_R_factor_gt           0.0994
_refine_ls_wR_factor_ref         0.2750
_refine_ls_wR_factor_gt          0.2720
_refine_ls_goodness_of_fit_ref   1.144
_refine_ls_restrained_S_all      1.143
_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 0.0625(2) 0.6244(3) 0.17269(9) 0.0302(6) Uani 1 1 d . . . . .
N2 N 0.4498(2) 0.3859(3) 0.08755(9) 0.0308(7) Uani 1 1 d . . . . .
C1 C 0.1613(3) 0.5652(4) 0.15155(11) 0.0286(7) Uani 1 1 d . . . . .
C2 C 0.2490(3) 0.5045(5) 0.17489(11) 0.0356(8) Uani 1 1 d . . . . .
H2 H 0.244455 0.501195 0.205880 0.043 Uiso 1 1 calc R U . . .
C3 C 0.3443(3) 0.4477(4) 0.15403(12) 0.0333(8) Uani 1 1 d . . . . .
H3 H 0.403841 0.409128 0.171335 0.040 Uiso 1 1 calc R U . . .
C4 C 0.3546(3) 0.4459(4) 0.10954(11) 0.0286(7) Uani 1 1 d . . . . .
C5 C 0.2629(3) 0.5042(4) 0.08367(11) 0.0266(7) Uani 1 1 d . . . . .
C6 C 0.2636(3) 0.4978(4) 0.03744(11) 0.0315(8) Uani 1 1 d . . . . .
H6 H 0.325813 0.454730 0.022801 0.038 Uiso 1 1 calc R U . . .
C7 C 0.1749(3) 0.5534(4) 0.01347(11) 0.0357(8) Uani 1 1 d . . . . .
H7 H 0.175754 0.546935 -0.017520 0.043 Uiso 1 1 calc R U . . .
C8 C 0.0835(3) 0.6194(4) 0.03463(12) 0.0337(8) Uani 1 1 d . . . . .
H8 H 0.024024 0.660019 0.017780 0.040 Uiso 1 1 calc R U . . .
C9 C 0.0792(3) 0.6259(4) 0.07907(11) 0.0299(7) Uani 1 1 d . . . . .
H9 H 0.016398 0.670344 0.092919 0.036 Uiso 1 1 calc R U . . .
C10 C 0.1683(3) 0.5666(4) 0.10508(11) 0.0275(7) Uani 1 1 d . . . . .
C11 C 0.0913(3) 0.7542(4) 0.19636(11) 0.0339(8) Uani 1 1 d . . . . .
H11A H 0.149447 0.732530 0.218795 0.041 Uiso 1 1 calc R U . . .
H11B H 0.022498 0.788867 0.211637 0.041 Uiso 1 1 calc R U . . .
C12 C 0.1358(3) 0.8690(4) 0.16691(12) 0.0362(8) Uani 1 1 d . . . . .
H12A H 0.077840 0.889677 0.144308 0.043 Uiso 1 1 calc R U . . .
H12B H 0.204811 0.834229 0.151805 0.043 Uiso 1 1 calc R U . . .
C13 C 0.1656(3) 1.0065(5) 0.19100(13) 0.0399(9) Uani 1 1 d . . . . .
H13A H 0.191440 1.076477 0.169199 0.048 Uiso 1 1 calc R U . . .
H13B H 0.095543 1.043703 0.204736 0.048 Uiso 1 1 calc R U . . .
C14 C 0.2579(3) 0.9923(5) 0.22645(13) 0.0410(9) Uani 1 1 d . . . . .
H14A H 0.269375 1.085171 0.240406 0.049 Uiso 1 1 calc R U . . .
H14B H 0.230402 0.926707 0.249231 0.049 Uiso 1 1 calc R U . . .
C15 C 0.3723(3) 0.9395(5) 0.20942(13) 0.0434(10) Uani 1 1 d . . . . .
H15A H 0.402888 1.008771 0.188300 0.052 Uiso 1 1 calc R U . . .
H15B H 0.360233 0.850011 0.193575 0.052 Uiso 1 1 calc R U . . .
C16 C 0.4604(3) 0.9159(5) 0.24556(13) 0.0422(9) Uani 1 1 d . . . . .
H16A H 0.428012 0.850819 0.267529 0.051 Uiso 1 1 calc R U . . .
H16B H 0.475477 1.006630 0.260340 0.051 Uiso 1 1 calc R U . . .
C17 C 0.5733(3) 0.8556(5) 0.22911(13) 0.0396(9) Uani 1 1 d . . . . .
H17A H 0.616919 0.819677 0.254471 0.048 Uiso 1 1 calc R U . . .
H17B H 0.556833 0.774675 0.209738 0.048 Uiso 1 1 calc R U . . .
C18 C 0.6472(3) 0.9596(4) 0.20438(13) 0.0389(9) Uani 1 1 d . . . . .
H18A H 0.660910 1.042638 0.223160 0.047 Uiso 1 1 calc R U . . .
H18B H 0.605449 0.991817 0.178101 0.047 Uiso 1 1 calc R U . . .
C19 C 0.7624(3) 0.8985(4) 0.19016(13) 0.0388(9) Uani 1 1 d . . . . .
H19A H 0.804293 0.867693 0.216578 0.047 Uiso 1 1 calc R U . . .
H19B H 0.807468 0.974287 0.176263 0.047 Uiso 1 1 calc R U . . .
C20 C 0.7551(3) 0.7740(4) 0.15826(12) 0.0364(8) Uani 1 1 d . . . . .
H20A H 0.832816 0.737948 0.152746 0.044 Uiso 1 1 calc R U . . .
H20B H 0.710691 0.697565 0.172085 0.044 Uiso 1 1 calc R U . . .
C21 C 0.6997(4) 0.8120(5) 0.11449(13) 0.0431(9) Uani 1 1 d . . . . .
H21A H 0.628348 0.864010 0.120375 0.052 Uiso 1 1 calc R U . . .
H21B H 0.751354 0.876241 0.098507 0.052 Uiso 1 1 calc R U . . .
C22 C 0.6722(4) 0.6867(5) 0.08495(13) 0.0414(9) Uani 1 1 d . . . . .
H22A H 0.648523 0.721792 0.055869 0.050 Uiso 1 1 calc R U . . .
H22B H 0.741863 0.629487 0.080959 0.050 Uiso 1 1 calc R U . . .
C23 C 0.5783(3) 0.5939(4) 0.10346(13) 0.0390(9) Uani 1 1 d . . . . .
H23A H 0.516375 0.654563 0.114678 0.047 Uiso 1 1 calc R U . . .
H23B H 0.609148 0.539635 0.128416 0.047 Uiso 1 1 calc R U . . .
C24 C 0.5290(3) 0.4918(4) 0.06988(12) 0.0338(8) Uani 1 1 d . . . . .
H24A H 0.488613 0.546786 0.047183 0.041 Uiso 1 1 calc R U . . .
H24B H 0.592749 0.442173 0.055427 0.041 Uiso 1 1 calc R U . . .
C25 C 0.5085(3) 0.2722(4) 0.11121(12) 0.0348(8) Uani 1 1 d . . . . .
H25A H 0.453663 0.224911 0.130895 0.042 Uiso 1 1 calc R U . . .
H25B H 0.569607 0.313177 0.129506 0.042 Uiso 1 1 calc R U . . .
C26 C 0.5598(3) 0.1642(4) 0.08057(14) 0.0392(9) Uani 1 1 d . U . . .
H26A H 0.600693 0.092905 0.098185 0.047 Uiso 1 1 calc R U . A 1
H26B H 0.616497 0.211534 0.061706 0.047 Uiso 1 1 calc R U . A 1
C27 C 0.4731(4) 0.0893(6) 0.05146(18) 0.0393(13) Uani 0.843(10) 1 d . U P B 1
H27A H 0.436184 0.159933 0.032386 0.047 Uiso 0.843(10) 1 calc R U P B 1
H27B H 0.514280 0.022461 0.032334 0.047 Uiso 0.843(10) 1 calc R U P B 1
C28 C 0.3811(4) 0.0094(6) 0.07591(17) 0.0422(14) Uani 0.843(10) 1 d . U P B 1
H28A H 0.332170 0.077338 0.091627 0.051 Uiso 0.843(10) 1 calc R U P B 1
H28B H 0.417355 -0.052389 0.097945 0.051 Uiso 0.843(10) 1 calc R U P B 1
C127 C 0.4762(16) 0.026(3) 0.0742(8) 0.033(6) Uani 0.157(10) 1 d D U P B 2
H12C H 0.517401 -0.048746 0.058306 0.039 Uiso 0.157(10) 1 calc R U P B 2
H12D H 0.453791 -0.011167 0.103192 0.039 Uiso 0.157(10) 1 calc R U P B 2
C128 C 0.3696(14) 0.0693(18) 0.0485(7) 0.029(6) Uani 0.157(10) 1 d D . P B 2
H12E H 0.389096 0.106948 0.019239 0.035 Uiso 0.157(10) 1 calc R U P B 2
H12F H 0.323334 0.139150 0.064567 0.035 Uiso 0.157(10) 1 calc R U P B 2
C29 C 0.3061(4) -0.0811(5) 0.04519(16) 0.0514(11) Uani 1 1 d D . . . .
H29A H 0.356202 -0.150884 0.030815 0.062 Uiso 1 1 calc R U . B 1
H29B H 0.251873 -0.134240 0.063619 0.062 Uiso 1 1 calc R U . B 1
C30 C 0.2376(4) -0.0069(5) 0.00945(15) 0.0527(11) Uani 1 1 d . . . . .
H30A H 0.291079 0.027588 -0.013135 0.063 Uiso 1 1 calc R U . . .
H30B H 0.186772 -0.076561 -0.004599 0.063 Uiso 1 1 calc R U . . .
C31 C 0.1657(4) 0.1164(5) 0.02526(15) 0.0519(11) Uani 1 1 d . . . . .
H31A H 0.216953 0.188891 0.037648 0.062 Uiso 1 1 calc R U . . .
H31B H 0.126337 0.158541 -0.000185 0.062 Uiso 1 1 calc R U . . .
C32 C 0.0774(4) 0.0777(5) 0.05946(14) 0.0434(9) Uani 1 1 d . . . . .
H32A H 0.117061 0.036058 0.084927 0.052 Uiso 1 1 calc R U . . .
H32B H 0.026832 0.004454 0.047104 0.052 Uiso 1 1 calc R U . . .
C33 C 0.0039(4) 0.1995(4) 0.07545(13) 0.0420(9) Uani 1 1 d . . . . .
H33A H 0.054010 0.275642 0.086262 0.050 Uiso 1 1 calc R U . . .
H33B H -0.040646 0.237057 0.050576 0.050 Uiso 1 1 calc R U . . .
C34 C -0.0773(3) 0.1562(4) 0.11173(13) 0.0399(9) Uani 1 1 d . . . . .
H34A H -0.031704 0.128388 0.137553 0.048 Uiso 1 1 calc R U . . .
H34B H -0.120055 0.072229 0.101926 0.048 Uiso 1 1 calc R U . . .
C35 C -0.1625(3) 0.2678(4) 0.12585(14) 0.0400(9) Uani 1 1 d . . . . .
H35A H -0.211127 0.227559 0.149095 0.048 Uiso 1 1 calc R U . . .
H35B H -0.212328 0.289713 0.100642 0.048 Uiso 1 1 calc R U . . .
C36 C -0.1115(3) 0.4053(4) 0.14273(13) 0.0361(8) Uani 1 1 d . . . . .
H36A H -0.174155 0.467912 0.152207 0.043 Uiso 1 1 calc R U . . .
H36B H -0.071123 0.452591 0.118436 0.043 Uiso 1 1 calc R U . . .
C37 C -0.0285(3) 0.3856(4) 0.18091(12) 0.0356(8) Uani 1 1 d . . . . .
H37A H -0.064345 0.324449 0.203170 0.043 Uiso 1 1 calc R U . . .
H37B H 0.040685 0.337351 0.170167 0.043 Uiso 1 1 calc R U . . .
C38 C 0.0059(3) 0.5242(4) 0.20230(12) 0.0364(9) Uani 1 1 d . . . . .
H38A H -0.063006 0.569372 0.214473 0.044 Uiso 1 1 calc R U . . .
H38B H 0.057850 0.503598 0.227000 0.044 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 C1 1.444(4) . ?
N1 C11 1.470(5) . ?
N1 C38 1.474(5) . ?
N2 C4 1.424(4) . ?
N2 C25 1.472(5) . ?
N2 C24 1.474(5) . ?
C1 C2 1.379(5) . ?
C1 C10 1.424(5) . ?
C2 C3 1.398(5) . ?
C2 H2 0.9500 . ?
C3 C4 1.367(5) . ?
C3 H3 0.9500 . ?
C4 C5 1.447(4) . ?
C5 C6 1.416(5) . ?
C5 C10 1.420(5) . ?
C6 C7 1.379(5) . ?
C6 H6 0.9500 . ?
C7 C8 1.403(5) . ?
C7 H7 0.9500 . ?
C8 C9 1.362(5) . ?
C8 H8 0.9500 . ?
C9 C10 1.430(4) . ?
C9 H9 0.9500 . ?
C11 C12 1.510(5) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 C13 1.541(5) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 C14 1.539(5) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C14 C15 1.527(5) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C15 C16 1.530(5) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C16 C17 1.531(5) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C17 C18 1.519(6) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C18 C19 1.536(5) . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C19 C20 1.537(5) . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
C20 C21 1.531(5) . ?
C20 H20A 0.9900 . ?
C20 H20B 0.9900 . ?
C21 C22 1.531(6) . ?
C21 H21A 0.9900 . ?
C21 H21B 0.9900 . ?
C22 C23 1.522(5) . ?
C22 H22A 0.9900 . ?
C22 H22B 0.9900 . ?
C23 C24 1.528(5) . ?
C23 H23A 0.9900 . ?
C23 H23B 0.9900 . ?
C24 H24A 0.9900 . ?
C24 H24B 0.9900 . ?
C25 C26 1.516(5) . ?
C25 H25A 0.9900 . ?
C25 H25B 0.9900 . ?
C26 C27 1.528(6) . ?
C26 C127 1.65(2) . ?
C26 H26A 0.9900 . ?
C26 H26B 0.9900 . ?
C27 C28 1.518(7) . ?
C27 H27A 0.9900 . ?
C27 H27B 0.9900 . ?
C28 C29 1.549(6) . ?
C28 H28A 0.9900 . ?
C28 H28B 0.9900 . ?
C127 C128 1.535(17) . ?
C127 H12C 0.9900 . ?
C127 H12D 0.9900 . ?
C128 C29 1.616(16) . ?
C128 H12E 0.9900 . ?
C128 H12F 0.9900 . ?
C29 C30 1.529(7) . ?
C29 H29A 0.9900 . ?
C29 H29B 0.9900 . ?
C30 C31 1.524(7) . ?
C30 H30A 0.9900 . ?
C30 H30B 0.9900 . ?
C31 C32 1.520(6) . ?
C31 H31A 0.9900 . ?
C31 H31B 0.9900 . ?
C32 C33 1.525(6) . ?
C32 H32A 0.9900 . ?
C32 H32B 0.9900 . ?
C33 C34 1.521(6) . ?
C33 H33A 0.9900 . ?
C33 H33B 0.9900 . ?
C34 C35 1.521(6) . ?
C34 H34A 0.9900 . ?
C34 H34B 0.9900 . ?
C35 C36 1.528(5) . ?
C35 H35A 0.9900 . ?
C35 H35B 0.9900 . ?
C36 C37 1.532(5) . ?
C36 H36A 0.9900 . ?
C36 H36B 0.9900 . ?
C37 C38 1.526(6) . ?
C37 H37A 0.9900 . ?
C37 H37B 0.9900 . ?
C38 H38A 0.9900 . ?
C38 H38B 0.9900 . ?

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 C11 111.3(3) . . ?
C1 N1 C38 112.7(3) . . ?
C11 N1 C38 110.1(3) . . ?
C4 N2 C25 115.5(3) . . ?
C4 N2 C24 113.3(3) . . ?
C25 N2 C24 112.7(3) . . ?
C2 C1 C10 118.5(3) . . ?
C2 C1 N1 122.1(3) . . ?
C10 C1 N1 119.4(3) . . ?
C1 C2 C3 121.6(3) . . ?
C1 C2 H2 119.2 . . ?
C3 C2 H2 119.2 . . ?
C4 C3 C2 122.1(3) . . ?
C4 C3 H3 119.0 . . ?
C2 C3 H3 119.0 . . ?
C3 C4 N2 123.1(3) . . ?
C3 C4 C5 118.2(3) . . ?
N2 C4 C5 118.7(3) . . ?
C6 C5 C10 119.0(3) . . ?
C6 C5 C4 121.6(3) . . ?
C10 C5 C4 119.4(3) . . ?
C7 C6 C5 120.6(3) . . ?
C7 C6 H6 119.7 . . ?
C5 C6 H6 119.7 . . ?
C6 C7 C8 120.3(3) . . ?
C6 C7 H7 119.9 . . ?
C8 C7 H7 119.9 . . ?
C9 C8 C7 120.7(3) . . ?
C9 C8 H8 119.7 . . ?
C7 C8 H8 119.7 . . ?
C8 C9 C10 120.6(3) . . ?
C8 C9 H9 119.7 . . ?
C10 C9 H9 119.7 . . ?
C5 C10 C1 120.1(3) . . ?
C5 C10 C9 118.7(3) . . ?
C1 C10 C9 121.1(3) . . ?
N1 C11 C12 113.2(3) . . ?
N1 C11 H11A 108.9 . . ?
C12 C11 H11A 108.9 . . ?
N1 C11 H11B 108.9 . . ?
C12 C11 H11B 108.9 . . ?
H11A C11 H11B 107.8 . . ?
C11 C12 C13 114.0(3) . . ?
C11 C12 H12A 108.7 . . ?
C13 C12 H12A 108.7 . . ?
C11 C12 H12B 108.7 . . ?
C13 C12 H12B 108.7 . . ?
H12A C12 H12B 107.6 . . ?
C14 C13 C12 115.0(3) . . ?
C14 C13 H13A 108.5 . . ?
C12 C13 H13A 108.5 . . ?
C14 C13 H13B 108.5 . . ?
C12 C13 H13B 108.5 . . ?
H13A C13 H13B 107.5 . . ?
C15 C14 C13 114.1(3) . . ?
C15 C14 H14A 108.7 . . ?
C13 C14 H14A 108.7 . . ?
C15 C14 H14B 108.7 . . ?
C13 C14 H14B 108.7 . . ?
H14A C14 H14B 107.6 . . ?
C14 C15 C16 113.4(3) . . ?
C14 C15 H15A 108.9 . . ?
C16 C15 H15A 108.9 . . ?
C14 C15 H15B 108.9 . . ?
C16 C15 H15B 108.9 . . ?
H15A C15 H15B 107.7 . . ?
C15 C16 C17 113.8(3) . . ?
C15 C16 H16A 108.8 . . ?
C17 C16 H16A 108.8 . . ?
C15 C16 H16B 108.8 . . ?
C17 C16 H16B 108.8 . . ?
H16A C16 H16B 107.7 . . ?
C18 C17 C16 114.5(4) . . ?
C18 C17 H17A 108.6 . . ?
C16 C17 H17A 108.6 . . ?
C18 C17 H17B 108.6 . . ?
C16 C17 H17B 108.6 . . ?
H17A C17 H17B 107.6 . . ?
C17 C18 C19 113.5(3) . . ?
C17 C18 H18A 108.9 . . ?
C19 C18 H18A 108.9 . . ?
C17 C18 H18B 108.9 . . ?
C19 C18 H18B 108.9 . . ?
H18A C18 H18B 107.7 . . ?
C18 C19 C20 115.0(3) . . ?
C18 C19 H19A 108.5 . . ?
C20 C19 H19A 108.5 . . ?
C18 C19 H19B 108.5 . . ?
C20 C19 H19B 108.5 . . ?
H19A C19 H19B 107.5 . . ?
C21 C20 C19 113.4(3) . . ?
C21 C20 H20A 108.9 . . ?
C19 C20 H20A 108.9 . . ?
C21 C20 H20B 108.9 . . ?
C19 C20 H20B 108.9 . . ?
H20A C20 H20B 107.7 . . ?
C22 C21 C20 114.9(4) . . ?
C22 C21 H21A 108.5 . . ?
C20 C21 H21A 108.5 . . ?
C22 C21 H21B 108.5 . . ?
C20 C21 H21B 108.5 . . ?
H21A C21 H21B 107.5 . . ?
C23 C22 C21 112.6(3) . . ?
C23 C22 H22A 109.1 . . ?
C21 C22 H22A 109.1 . . ?
C23 C22 H22B 109.1 . . ?
C21 C22 H22B 109.1 . . ?
H22A C22 H22B 107.8 . . ?
C22 C23 C24 113.1(3) . . ?
C22 C23 H23A 109.0 . . ?
C24 C23 H23A 109.0 . . ?
C22 C23 H23B 109.0 . . ?
C24 C23 H23B 109.0 . . ?
H23A C23 H23B 107.8 . . ?
N2 C24 C23 115.3(3) . . ?
N2 C24 H24A 108.5 . . ?
C23 C24 H24A 108.5 . . ?
N2 C24 H24B 108.5 . . ?
C23 C24 H24B 108.5 . . ?
H24A C24 H24B 107.5 . . ?
N2 C25 C26 112.3(3) . . ?
N2 C25 H25A 109.1 . . ?
C26 C25 H25A 109.1 . . ?
N2 C25 H25B 109.1 . . ?
C26 C25 H25B 109.1 . . ?
H25A C25 H25B 107.9 . . ?
C25 C26 C27 114.3(3) . . ?
C25 C26 C127 112.0(9) . . ?
C25 C26 H26A 108.7 . . ?
C27 C26 H26A 108.7 . . ?
C25 C26 H26B 108.7 . . ?
C27 C26 H26B 108.7 . . ?
H26A C26 H26B 107.6 . . ?
C28 C27 C26 114.8(4) . . ?
C28 C27 H27A 108.6 . . ?
C26 C27 H27A 108.6 . . ?
C28 C27 H27B 108.6 . . ?
C26 C27 H27B 108.6 . . ?
H27A C27 H27B 107.5 . . ?
C27 C28 C29 112.6(4) . . ?
C27 C28 H28A 109.1 . . ?
C29 C28 H28A 109.1 . . ?
C27 C28 H28B 109.1 . . ?
C29 C28 H28B 109.1 . . ?
H28A C28 H28B 107.8 . . ?
C128 C127 C26 109.4(16) . . ?
C128 C127 H12C 109.8 . . ?
C26 C127 H12C 109.8 . . ?
C128 C127 H12D 109.8 . . ?
C26 C127 H12D 109.8 . . ?
H12C C127 H12D 108.2 . . ?
C127 C128 C29 99.8(14) . . ?
C127 C128 H12E 111.8 . . ?
C29 C128 H12E 111.8 . . ?
C127 C128 H12F 111.8 . . ?
C29 C128 H12F 111.8 . . ?
H12E C128 H12F 109.5 . . ?
C30 C29 C28 118.4(4) . . ?
C30 C29 C128 83.0(7) . . ?
C30 C29 H29A 107.7 . . ?
C28 C29 H29A 107.7 . . ?
C30 C29 H29B 107.7 . . ?
C28 C29 H29B 107.7 . . ?
H29A C29 H29B 107.1 . . ?
C31 C30 C29 114.8(4) . . ?
C31 C30 H30A 108.6 . . ?
C29 C30 H30A 108.6 . . ?
C31 C30 H30B 108.6 . . ?
C29 C30 H30B 108.6 . . ?
H30A C30 H30B 107.5 . . ?
C32 C31 C30 114.3(4) . . ?
C32 C31 H31A 108.7 . . ?
C30 C31 H31A 108.7 . . ?
C32 C31 H31B 108.7 . . ?
C30 C31 H31B 108.7 . . ?
H31A C31 H31B 107.6 . . ?
C31 C32 C33 115.1(4) . . ?
C31 C32 H32A 108.5 . . ?
C33 C32 H32A 108.5 . . ?
C31 C32 H32B 108.5 . . ?
C33 C32 H32B 108.5 . . ?
H32A C32 H32B 107.5 . . ?
C34 C33 C32 112.6(3) . . ?
C34 C33 H33A 109.1 . . ?
C32 C33 H33A 109.1 . . ?
C34 C33 H33B 109.1 . . ?
C32 C33 H33B 109.1 . . ?
H33A C33 H33B 107.8 . . ?
C33 C34 C35 115.6(3) . . ?
C33 C34 H34A 108.4 . . ?
C35 C34 H34A 108.4 . . ?
C33 C34 H34B 108.4 . . ?
C35 C34 H34B 108.4 . . ?
H34A C34 H34B 107.4 . . ?
C34 C35 C36 115.8(3) . . ?
C34 C35 H35A 108.3 . . ?
C36 C35 H35A 108.3 . . ?
C34 C35 H35B 108.3 . . ?
C36 C35 H35B 108.3 . . ?
H35A C35 H35B 107.4 . . ?
C35 C36 C37 113.7(3) . . ?
C35 C36 H36A 108.8 . . ?
C37 C36 H36A 108.8 . . ?
C35 C36 H36B 108.8 . . ?
C37 C36 H36B 108.8 . . ?
H36A C36 H36B 107.7 . . ?
C38 C37 C36 112.9(3) . . ?
C38 C37 H37A 109.0 . . ?
C36 C37 H37A 109.0 . . ?
C38 C37 H37B 109.0 . . ?
C36 C37 H37B 109.0 . . ?
H37A C37 H37B 107.8 . . ?
N1 C38 C37 114.5(3) . . ?
N1 C38 H38A 108.6 . . ?
C37 C38 H38A 108.6 . . ?
N1 C38 H38B 108.6 . . ?
C37 C38 H38B 108.6 . . ?
H38A C38 H38B 107.6 . . ?

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
C11 N1 C1 C2 70.1(4) . . . . ?
C38 N1 C1 C2 -54.2(4) . . . . ?
C11 N1 C1 C10 -111.1(3) . . . . ?
C38 N1 C1 C10 124.6(3) . . . . ?
C10 C1 C2 C3 1.3(6) . . . . ?
N1 C1 C2 C3 -179.9(4) . . . . ?
C1 C2 C3 C4 -1.7(6) . . . . ?
C2 C3 C4 N2 -178.6(4) . . . . ?
C2 C3 C4 C5 -0.4(6) . . . . ?
C25 N2 C4 C3 27.2(5) . . . . ?
C24 N2 C4 C3 -104.9(4) . . . . ?
C25 N2 C4 C5 -150.9(3) . . . . ?
C24 N2 C4 C5 77.0(4) . . . . ?
C3 C4 C5 C6 -175.7(3) . . . . ?
N2 C4 C5 C6 2.5(5) . . . . ?
C3 C4 C5 C10 2.8(5) . . . . ?
N2 C4 C5 C10 -179.0(3) . . . . ?
C10 C5 C6 C7 1.1(5) . . . . ?
C4 C5 C6 C7 179.7(3) . . . . ?
C5 C6 C7 C8 1.1(6) . . . . ?
C6 C7 C8 C9 -2.0(6) . . . . ?
C7 C8 C9 C10 0.5(6) . . . . ?
C6 C5 C10 C1 175.4(3) . . . . ?
C4 C5 C10 C1 -3.2(5) . . . . ?
C6 C5 C10 C9 -2.5(5) . . . . ?
C4 C5 C10 C9 178.9(3) . . . . ?
C2 C1 C10 C5 1.1(5) . . . . ?
N1 C1 C10 C5 -177.7(3) . . . . ?
C2 C1 C10 C9 179.0(3) . . . . ?
N1 C1 C10 C9 0.1(5) . . . . ?
C8 C9 C10 C5 1.7(5) . . . . ?
C8 C9 C10 C1 -176.1(3) . . . . ?
C1 N1 C11 C12 61.6(4) . . . . ?
C38 N1 C11 C12 -172.7(3) . . . . ?
N1 C11 C12 C13 179.5(3) . . . . ?
C11 C12 C13 C14 60.2(4) . . . . ?
C12 C13 C14 C15 59.9(5) . . . . ?
C13 C14 C15 C16 -175.8(4) . . . . ?
C14 C15 C16 C17 176.9(4) . . . . ?
C15 C16 C17 C18 73.5(5) . . . . ?
C16 C17 C18 C19 177.2(3) . . . . ?
C17 C18 C19 C20 62.3(4) . . . . ?
C18 C19 C20 C21 62.6(5) . . . . ?
C19 C20 C21 C22 -170.0(3) . . . . ?
C20 C21 C22 C23 67.7(5) . . . . ?
C21 C22 C23 C24 165.3(3) . . . . ?
C4 N2 C24 C23 57.7(4) . . . . ?
C25 N2 C24 C23 -75.7(4) . . . . ?
C22 C23 C24 N2 171.5(3) . . . . ?
C4 N2 C25 C26 148.6(3) . . . . ?
C24 N2 C25 C26 -79.0(4) . . . . ?
N2 C25 C26 C27 -60.8(5) . . . . ?
N2 C25 C26 C127 -97.1(9) . . . . ?
C25 C26 C27 C28 -59.3(6) . . . . ?
C26 C27 C28 C29 -172.0(4) . . . . ?
C25 C26 C127 C128 69.1(18) . . . . ?
C26 C127 C128 C29 178.0(13) . . . . ?
C27 C28 C29 C30 -61.2(6) . . . . ?
C127 C128 C29 C30 -164.0(15) . . . . ?
C28 C29 C30 C31 -50.8(6) . . . . ?
C128 C29 C30 C31 -64.1(9) . . . . ?
C29 C30 C31 C32 -59.7(6) . . . . ?
C30 C31 C32 C33 -179.5(4) . . . . ?
C31 C32 C33 C34 -176.2(4) . . . . ?
C32 C33 C34 C35 -173.4(3) . . . . ?
C33 C34 C35 C36 -59.0(5) . . . . ?
C34 C35 C36 C37 -55.9(5) . . . . ?
C35 C36 C37 C38 -170.3(3) . . . . ?
C1 N1 C38 C37 -55.5(4) . . . . ?
C11 N1 C38 C37 179.6(3) . . . . ?
C36 C37 C38 N1 -59.7(4) . . . . ?

_refine_diff_density_max         0.448
_refine_diff_density_min         -0.412
_refine_diff_density_rms         0.087


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: ethanol'
_chemical_compound_source        no
