# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2019

####################################################################### 
# 
# 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_atc12
_database_code_depnum_ccdc_archive 'CCDC 1884818'
loop_
_audit_author_name
_audit_author_address
'Kuniharu Nomoto'
;Tokyo University of Science
Japan
;
_audit_update_record             
;
2018-12-13 deposited with the CCDC.	2019-04-24 downloaded from the CCDC.
;
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         'C17 H29 N5, C17 H30 N2 O2'
_chemical_formula_sum            'C34 H59 N7 O2'
_chemical_formula_iupac          ?
_chemical_formula_weight         597.88

_chemical_melting_point          ?

_space_group_crystal_system      triclinic
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.4030(14)
_cell_length_b                   10.9764(18)
_cell_length_c                   20.319(3)
_cell_angle_alpha                99.433(2)
_cell_angle_beta                 94.128(2)
_cell_angle_gamma                109.784(2)
_cell_volume                     1723.2(5)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    1767
_cell_measurement_theta_min      2.6005
_cell_measurement_theta_max      26.3911
_cell_measurement_temperature    173

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.327
_exptl_crystal_size_mid          0.137
_exptl_crystal_size_min          0.028
_exptl_crystal_density_diffrn    1.152
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             656

_exptl_absorpt_coefficient_mu    0.073
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2014/5 (Bruker AXS Inc.)'
_exptl_absorpt_correction_T_min  0.82
_exptl_absorpt_correction_T_max  1.00

_exptl_special_details           
;
;

_diffrn_ambient_temperature      173

_diffrn_source                   ?
_diffrn_source_type              ?

_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  ?

_diffrn_measurement_device_type  'Bruker SMART APEX II CCD area detector'
_diffrn_measurement_method       'φ and ω scans'

_diffrn_detector_area_resol_mean 8.3333

_diffrn_reflns_number            9313
_diffrn_reflns_av_R_equivalents  0.0206
_diffrn_reflns_av_unetI/netI     0.0590
_diffrn_reflns_theta_min         2.01
_diffrn_reflns_theta_max         26.79
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_max 0.957
_diffrn_measured_fraction_theta_full 0.980
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       12

_refine_special_details          
;
;

_reflns_number_total             7058
_reflns_number_gt                4378
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.1122
_refine_ls_R_factor_gt           0.0652
_refine_ls_wR_factor_gt          0.1631
_refine_ls_wR_factor_ref         0.1955
_refine_ls_goodness_of_fit_ref   0.993
_refine_ls_restrained_S_all      0.993
_refine_ls_number_reflns         7058
_refine_ls_number_parameters     403
_refine_ls_number_restraints     0
_refine_ls_number_constraints    ?
_refine_ls_hydrogen_treatment    mixed
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1000P)²+0.2623P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?

_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.273
_refine_diff_density_min         -0.265
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_computing_data_collection       ?
_computing_cell_refinement       'SAINT V8.35A (Bruker AXS Inc., 2015)'
_computing_data_reduction        'SAINT V8.35A (Bruker AXS Inc., 2015)'
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C C1 0.1994(3) 0.4948(2) 0.37582(12) 0.0326(6) Uani d . . . 1 . .
H H1 0.1315 0.5377 0.357 0.039 Uiso calc U . R 1 . .
C C2 0.4466(3) 0.4704(2) 0.39330(11) 0.0243(5) Uani d . . . 1 . .
C C3 0.3810(3) 0.3730(2) 0.42987(11) 0.0219(5) Uani d . . . 1 . .
C C4 0.2093(3) 0.3405(2) 0.43888(11) 0.0243(5) Uani d . . . 1 . .
C C5 0.6473(3) 0.4045(2) 0.43217(11) 0.0253(5) Uani d . . . 1 . .
H H5 0.7565 0.3983 0.4412 0.03 Uiso calc U . R 1 . .
C C6 0.7424(3) 0.5856(2) 0.36462(12) 0.0272(5) Uani d . . . 1 . .
H H6A 0.8584 0.5893 0.3805 0.033 Uiso calc U . R 1 . .
H H6B 0.7367 0.6742 0.38 0.033 Uiso calc U . R 1 . .
C C7 0.7122(3) 0.5513(2) 0.28811(11) 0.0294(6) Uani d . . . 1 . .
H H7A 0.7944 0.6234 0.2709 0.035 Uiso calc U . R 1 . .
H H7B 0.596 0.5479 0.2727 0.035 Uiso calc U . R 1 . .
C C8 0.7294(3) 0.4212(2) 0.25705(11) 0.0295(6) Uani d . . . 1 . .
H H8A 0.637 0.3474 0.2687 0.035 Uiso calc U . R 1 . .
H H8B 0.8397 0.4192 0.2765 0.035 Uiso calc U . R 1 . .
C C9 0.7208(3) 0.4011(2) 0.18072(12) 0.0316(6) Uani d . . . 1 . .
H H9A 0.611 0.4043 0.1616 0.038 Uiso calc U . R 1 . .
H H9B 0.8136 0.4751 0.1694 0.038 Uiso calc U . R 1 . .
C C10 0.7363(3) 0.2721(2) 0.14766(12) 0.0310(6) Uani d . . . 1 . .
H H10A 0.6401 0.1979 0.157 0.037 Uiso calc U . R 1 . .
H H10B 0.8434 0.2667 0.1684 0.037 Uiso calc U . R 1 . .
C C11 0.7365(3) 0.2557(2) 0.07184(11) 0.0302(6) Uani d . . . 1 . .
H H11A 0.6307 0.2633 0.0512 0.036 Uiso calc U . R 1 . .
H H11B 0.8343 0.3288 0.0626 0.036 Uiso calc U . R 1 . .
C C12 0.7480(3) 0.1252(2) 0.03841(12) 0.0309(6) Uani d . . . 1 . .
H H12A 0.6485 0.0522 0.0466 0.037 Uiso calc U . R 1 . .
H H12B 0.8522 0.1166 0.0599 0.037 Uiso calc U . R 1 . .
C C13 0.7529(3) 0.1101(2) -0.03719(11) 0.0315(6) Uani d . . . 1 . .
H H13A 0.6487 0.1185 -0.0588 0.038 Uiso calc U . R 1 . .
H H13B 0.8525 0.183 -0.0455 0.038 Uiso calc U . R 1 . .
C C14 0.7644(3) -0.0211(2) -0.07004(12) 0.0316(6) Uani d . . . 1 . .
H H14A 0.6647 -0.0937 -0.0616 0.038 Uiso calc U . R 1 . .
H H14B 0.8683 -0.0294 -0.0481 0.038 Uiso calc U . R 1 . .
C C15 0.7701(3) -0.0382(2) -0.14568(12) 0.0319(6) Uani d . . . 1 . .
H H15A 0.6655 -0.0314 -0.1679 0.038 Uiso calc U . R 1 . .
H H15B 0.8693 0.0345 -0.1544 0.038 Uiso calc U . R 1 . .
C C16 0.7835(3) -0.1688(2) -0.17655(12) 0.0365(6) Uani d . . . 1 . .
H H16A 0.6849 -0.2413 -0.1673 0.044 Uiso calc U . R 1 . .
H H16B 0.8885 -0.1751 -0.1544 0.044 Uiso calc U . R 1 . .
C C17 0.7879(4) -0.1882(3) -0.25207(13) 0.0495(8) Uani d . . . 1 . .
H H17A 0.6801 -0.1898 -0.2748 0.074 Uiso calc U . R 1 . .
H H17B 0.8034 -0.2721 -0.2682 0.074 Uiso calc U . R 1 . .
H H17C 0.8828 -0.1153 -0.2619 0.074 Uiso calc U . R 1 . .
C C18 0.4002(3) 0.0926(2) 0.57032(11) 0.0231(5) Uani d . . . 1 . .
C C19 0.7050(3) 0.1638(2) 0.55649(11) 0.0240(5) Uani d . . . 1 . .
C C20 0.7236(3) 0.0709(2) 0.59633(11) 0.0241(5) Uani d . . . 1 . .
C C21 0.5843(3) -0.0036(2) 0.61850(11) 0.0252(5) Uani d . . . 1 . .
H H21 0.5957 -0.067 0.6434 0.03 Uiso calc U . R 1 . .
C C22 0.8955(3) 0.0615(3) 0.60962(14) 0.0357(6) Uani d . . . 1 . .
H H22A 0.8868 -0.0109 0.6333 0.054 Uiso calc U . R 1 . .
H H22B 0.9742 0.1448 0.6375 0.054 Uiso calc U . R 1 . .
H H22C 0.9385 0.0445 0.5668 0.054 Uiso calc U . R 1 . .
C C23 0.2786(3) -0.0847(2) 0.63231(11) 0.0255(5) Uani d . . . 1 . .
H H23A 0.2703 -0.177 0.6159 0.031 Uiso calc U . R 1 . .
H H23B 0.1723 -0.0753 0.6134 0.031 Uiso calc U . R 1 . .
C C24 0.2926(3) -0.0580(2) 0.70883(12) 0.0289(6) Uani d . . . 1 . .
H H24A 0.1994 -0.129 0.7221 0.035 Uiso calc U . R 1 . .
H H24B 0.4021 -0.0628 0.7274 0.035 Uiso calc U . R 1 . .
C C25 0.2839(3) 0.0746(2) 0.74074(11) 0.0289(6) Uani d . . . 1 . .
H H25A 0.1793 0.0832 0.7197 0.035 Uiso calc U . R 1 . .
H H4N 0.3833 0.1463 0.7314 0.035 Uiso calc U . R 1 . .
C C26 0.2827(3) 0.0914(2) 0.81662(12) 0.0309(6) Uani d . . . 1 . .
H H26A 0.1853 0.0179 0.8258 0.037 Uiso calc U . R 1 . .
H H26B 0.3888 0.0847 0.8375 0.037 Uiso calc U . R 1 . .
C C27 0.2694(3) 0.2213(2) 0.84977(12) 0.0325(6) Uani d . . . 1 . .
H H27A 0.1643 0.2287 0.8284 0.039 Uiso calc U . R 1 . .
H H27B 0.3679 0.2949 0.8413 0.039 Uiso calc U . R 1 . .
C C28 0.2655(3) 0.2363(2) 0.92542(12) 0.0330(6) Uani d . . . 1 . .
H H28A 0.3699 0.2277 0.9467 0.04 Uiso calc U . R 1 . .
H H28B 0.1661 0.1634 0.9338 0.04 Uiso calc U . R 1 . .
C C29 0.2544(3) 0.3674(2) 0.95897(12) 0.0324(6) Uani d . . . 1 . .
H H29A 0.3545 0.4402 0.951 0.039 Uiso calc U . R 1 . .
H H29B 0.1508 0.3764 0.9372 0.039 Uiso calc U . R 1 . .
C C30 0.2482(3) 0.3829(2) 1.03436(12) 0.0323(6) Uani d . . . 1 . .
H H30A 0.1476 0.3109 1.0427 0.039 Uiso calc U . R 1 . .
H H30B 0.3515 0.3739 1.0564 0.039 Uiso calc U . R 1 . .
C C31 0.2382(3) 0.5149(2) 1.06606(12) 0.0334(6) Uani d . . . 1 . .
H H31A 0.1362 0.524 1.0429 0.04 Uiso calc U . R 1 . .
H H31B 0.3397 0.5863 1.0578 0.04 Uiso calc U . R 1 . .
C C32 0.2289(3) 0.5357(2) 1.14130(12) 0.0330(6) Uani d . . . 1 . .
H H32A 0.1268 0.4655 1.15 0.04 Uiso calc U . R 1 . .
H H32B 0.3307 0.5271 1.1648 0.04 Uiso calc U . R 1 . .
C C33 0.2201(3) 0.6688(3) 1.17005(13) 0.0374(6) Uani d . . . 1 . .
H H33A 0.1212 0.6785 1.1449 0.045 Uiso calc U . R 1 . .
H H33B 0.3244 0.7386 1.1625 0.045 Uiso calc U . R 1 . .
C C34 0.2040(4) 0.6918(3) 1.24456(13) 0.0466(7) Uani d . . . 1 . .
H H34A 0.0978 0.6266 1.2524 0.07 Uiso calc U . R 1 . .
H H34B 0.2024 0.781 1.2592 0.07 Uiso calc U . R 1 . .
H H34C 0.3014 0.6828 1.2701 0.07 Uiso calc U . R 1 . .
H H1N 0.027(4) 0.247(3) 0.4877(14) 0.059(9) Uiso d . . . 1 . .
H H2N 0.193(4) 0.213(3) 0.4991(14) 0.048(8) Uiso d . . . 1 . .
H H3N 0.526(3) 0.221(3) 0.5174(13) 0.047(8) Uiso d . . . 1 . .
N N1 0.1173(2) 0.40326(19) 0.40971(10) 0.0291(5) Uani d . . . 1 . .
N N2 0.3614(2) 0.53547(19) 0.36418(10) 0.0293(5) Uani d . . . 1 . .
N N3 0.5097(2) 0.33223(18) 0.45460(9) 0.0246(4) Uani d . . . 1 . .
N N4 0.6169(2) 0.48918(18) 0.39472(9) 0.0244(4) Uani d . . . 1 . .
N N5 0.1312(3) 0.2510(2) 0.47455(11) 0.0297(5) Uani d . . . 1 . .
N N6 0.4253(2) 0.00552(18) 0.60749(9) 0.0229(4) Uani d . . . 1 . .
N N7 0.5418(2) 0.16612(18) 0.54602(10) 0.0233(4) Uani d . . . 1 . .
O O1 0.26181(19) 0.10488(16) 0.55897(8) 0.0320(4) Uani d . . . 1 . .
O O2 0.8207(2) 0.23792(16) 0.53189(9) 0.0356(4) Uani d . . . 1 . .


_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_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
C1 N2 . 1.333(3) ?
C1 N1 . 1.336(3) ?
C1 H1 . 0.95 ?
C2 N2 . 1.340(3) ?
C2 N4 . 1.373(3) ?
C2 C3 . 1.386(3) ?
C3 N3 . 1.394(3) ?
C3 C4 . 1.398(3) ?
C4 N5 . 1.337(3) ?
C4 N1 . 1.361(3) ?
C5 N3 . 1.322(3) ?
C5 N4 . 1.369(3) ?
C5 H5 . 0.95 ?
C6 N4 . 1.468(3) ?
C6 C7 . 1.520(3) ?
C6 H6A . 0.99 ?
C6 H6B . 0.99 ?
C7 C8 . 1.522(3) ?
C7 H7A . 0.99 ?
C7 H7B . 0.99 ?
C8 C9 . 1.523(3) ?
C8 H8A . 0.99 ?
C8 H8B . 0.99 ?
C9 C10 . 1.515(3) ?
C9 H9A . 0.99 ?
C9 H9B . 0.99 ?
C10 C11 . 1.522(3) ?
C10 H10A . 0.99 ?
C10 H10B . 0.99 ?
C11 C12 . 1.519(3) ?
C11 H11A . 0.99 ?
C11 H11B . 0.99 ?
C12 C13 . 1.523(3) ?
C12 H12A . 0.99 ?
C12 H12B . 0.99 ?
C13 C14 . 1.523(3) ?
C13 H13A . 0.99 ?
C13 H13B . 0.99 ?
C14 C15 . 1.524(3) ?
C14 H14A . 0.99 ?
C14 H14B . 0.99 ?
C15 C16 . 1.512(3) ?
C15 H15A . 0.99 ?
C15 H15B . 0.99 ?
C16 C17 . 1.519(3) ?
C16 H16A . 0.99 ?
C16 H16B . 0.99 ?
C17 H17A . 0.98 ?
C17 H17B . 0.98 ?
C17 H17C . 0.98 ?
C18 O1 . 1.225(3) ?
C18 N7 . 1.369(3) ?
C18 N6 . 1.371(3) ?
C19 O2 . 1.235(3) ?
C19 N7 . 1.382(3) ?
C19 C20 . 1.442(3) ?
C20 C21 . 1.338(3) ?
C20 C22 . 1.491(3) ?
C21 N6 . 1.379(3) ?
C21 H21 . 0.95 ?
C22 H22A . 0.98 ?
C22 H22B . 0.98 ?
C22 H22C . 0.98 ?
C23 N6 . 1.477(3) ?
C23 C24 . 1.523(3) ?
C23 H23A . 0.99 ?
C23 H23B . 0.99 ?
C24 C25 . 1.521(3) ?
C24 H24A . 0.99 ?
C24 H24B . 0.99 ?
C25 C26 . 1.524(3) ?
C25 H25A . 0.99 ?
C25 H4N . 0.99 ?
C26 C27 . 1.518(3) ?
C26 H26A . 0.99 ?
C26 H26B . 0.99 ?
C27 C28 . 1.523(3) ?
C27 H27A . 0.99 ?
C27 H27B . 0.99 ?
C28 C29 . 1.523(3) ?
C28 H28A . 0.99 ?
C28 H28B . 0.99 ?
C29 C30 . 1.520(3) ?
C29 H29A . 0.99 ?
C29 H29B . 0.99 ?
C30 C31 . 1.519(3) ?
C30 H30A . 0.99 ?
C30 H30B . 0.99 ?
C31 C32 . 1.520(3) ?
C31 H31A . 0.99 ?
C31 H31B . 0.99 ?
C32 C33 . 1.511(3) ?
C32 H32A . 0.99 ?
C32 H32B . 0.99 ?
C33 C34 . 1.517(3) ?
C33 H33A . 0.99 ?
C33 H33B . 0.99 ?
C34 H34A . 0.98 ?
C34 H34B . 0.98 ?
C34 H34C . 0.98 ?
N5 H1N . 0.92(3) ?
N5 H2N . 0.94(3) ?
N7 H3N . 0.93(3) ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
N2 C1 N1 . . 130.3(2) ?
N2 C1 H1 . . 114.9 ?
N1 C1 H1 . . 114.9 ?
N2 C2 N4 . . 127.2(2) ?
N2 C2 C3 . . 126.7(2) ?
N4 C2 C3 . . 106.1(2) ?
C2 C3 N3 . . 110.27(19) ?
C2 C3 C4 . . 117.1(2) ?
N3 C3 C4 . . 132.4(2) ?
N5 C4 N1 . . 118.5(2) ?
N5 C4 C3 . . 123.4(2) ?
N1 C4 C3 . . 118.1(2) ?
N3 C5 N4 . . 113.3(2) ?
N3 C5 H5 . . 123.3 ?
N4 C5 H5 . . 123.3 ?
N4 C6 C7 . . 112.38(18) ?
N4 C6 H6A . . 109.1 ?
C7 C6 H6A . . 109.1 ?
N4 C6 H6B . . 109.1 ?
C7 C6 H6B . . 109.1 ?
H6A C6 H6B . . 107.9 ?
C6 C7 C8 . . 115.0(2) ?
C6 C7 H7A . . 108.5 ?
C8 C7 H7A . . 108.5 ?
C6 C7 H7B . . 108.5 ?
C8 C7 H7B . . 108.5 ?
H7A C7 H7B . . 107.5 ?
C7 C8 C9 . . 112.5(2) ?
C7 C8 H8A . . 109.1 ?
C9 C8 H8A . . 109.1 ?
C7 C8 H8B . . 109.1 ?
C9 C8 H8B . . 109.1 ?
H8A C8 H8B . . 107.8 ?
C10 C9 C8 . . 114.2(2) ?
C10 C9 H9A . . 108.7 ?
C8 C9 H9A . . 108.7 ?
C10 C9 H9B . . 108.7 ?
C8 C9 H9B . . 108.7 ?
H9A C9 H9B . . 107.6 ?
C9 C10 C11 . . 114.0(2) ?
C9 C10 H10A . . 108.8 ?
C11 C10 H10A . . 108.8 ?
C9 C10 H10B . . 108.8 ?
C11 C10 H10B . . 108.8 ?
H10A C10 H10B . . 107.7 ?
C12 C11 C10 . . 114.0(2) ?
C12 C11 H11A . . 108.7 ?
C10 C11 H11A . . 108.7 ?
C12 C11 H11B . . 108.7 ?
C10 C11 H11B . . 108.7 ?
H11A C11 H11B . . 107.6 ?
C11 C12 C13 . . 114.1(2) ?
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 . . 113.5(2) ?
C14 C13 H13A . . 108.9 ?
C12 C13 H13A . . 108.9 ?
C14 C13 H13B . . 108.9 ?
C12 C13 H13B . . 108.9 ?
H13A C13 H13B . . 107.7 ?
C13 C14 C15 . . 114.5(2) ?
C13 C14 H14A . . 108.6 ?
C15 C14 H14A . . 108.6 ?
C13 C14 H14B . . 108.6 ?
C15 C14 H14B . . 108.6 ?
H14A C14 H14B . . 107.6 ?
C16 C15 C14 . . 113.1(2) ?
C16 C15 H15A . . 109.0 ?
C14 C15 H15A . . 109.0 ?
C16 C15 H15B . . 109.0 ?
C14 C15 H15B . . 109.0 ?
H15A C15 H15B . . 107.8 ?
C15 C16 C17 . . 113.9(2) ?
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 ?
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 ?
O1 C18 N7 . . 121.6(2) ?
O1 C18 N6 . . 123.2(2) ?
N7 C18 N6 . . 115.23(19) ?
O2 C19 N7 . . 119.5(2) ?
O2 C19 C20 . . 125.4(2) ?
N7 C19 C20 . . 115.08(19) ?
C21 C20 C19 . . 117.8(2) ?
C21 C20 C22 . . 123.7(2) ?
C19 C20 C22 . . 118.5(2) ?
C20 C21 N6 . . 124.2(2) ?
C20 C21 H21 . . 117.9 ?
N6 C21 H21 . . 117.9 ?
C20 C22 H22A . . 109.5 ?
C20 C22 H22B . . 109.5 ?
H22A C22 H22B . . 109.5 ?
C20 C22 H22C . . 109.5 ?
H22A C22 H22C . . 109.5 ?
H22B C22 H22C . . 109.5 ?
N6 C23 C24 . . 112.81(18) ?
N6 C23 H23A . . 109.0 ?
C24 C23 H23A . . 109.0 ?
N6 C23 H23B . . 109.0 ?
C24 C23 H23B . . 109.0 ?
H23A C23 H23B . . 107.8 ?
C25 C24 C23 . . 114.91(19) ?
C25 C24 H24A . . 108.5 ?
C23 C24 H24A . . 108.5 ?
C25 C24 H24B . . 108.5 ?
C23 C24 H24B . . 108.5 ?
H24A C24 H24B . . 107.5 ?
C24 C25 C26 . . 112.8(2) ?
C24 C25 H25A . . 109.0 ?
C26 C25 H25A . . 109.0 ?
C24 C25 H4N . . 109.0 ?
C26 C25 H4N . . 109.0 ?
H25A C25 H4N . . 107.8 ?
C27 C26 C25 . . 114.2(2) ?
C27 C26 H26A . . 108.7 ?
C25 C26 H26A . . 108.7 ?
C27 C26 H26B . . 108.7 ?
C25 C26 H26B . . 108.7 ?
H26A C26 H26B . . 107.6 ?
C26 C27 C28 . . 113.8(2) ?
C26 C27 H27A . . 108.8 ?
C28 C27 H27A . . 108.8 ?
C26 C27 H27B . . 108.8 ?
C28 C27 H27B . . 108.8 ?
H27A C27 H27B . . 107.7 ?
C27 C28 C29 . . 113.9(2) ?
C27 C28 H28A . . 108.8 ?
C29 C28 H28A . . 108.8 ?
C27 C28 H28B . . 108.8 ?
C29 C28 H28B . . 108.8 ?
H28A C28 H28B . . 107.7 ?
C30 C29 C28 . . 114.4(2) ?
C30 C29 H29A . . 108.7 ?
C28 C29 H29A . . 108.7 ?
C30 C29 H29B . . 108.7 ?
C28 C29 H29B . . 108.7 ?
H29A C29 H29B . . 107.6 ?
C31 C30 C29 . . 112.9(2) ?
C31 C30 H30A . . 109.0 ?
C29 C30 H30A . . 109.0 ?
C31 C30 H30B . . 109.0 ?
C29 C30 H30B . . 109.0 ?
H30A C30 H30B . . 107.8 ?
C30 C31 C32 . . 115.4(2) ?
C30 C31 H31A . . 108.4 ?
C32 C31 H31A . . 108.4 ?
C30 C31 H31B . . 108.4 ?
C32 C31 H31B . . 108.4 ?
H31A C31 H31B . . 107.5 ?
C33 C32 C31 . . 113.0(2) ?
C33 C32 H32A . . 109.0 ?
C31 C32 H32A . . 109.0 ?
C33 C32 H32B . . 109.0 ?
C31 C32 H32B . . 109.0 ?
H32A C32 H32B . . 107.8 ?
C32 C33 C34 . . 114.9(2) ?
C32 C33 H33A . . 108.6 ?
C34 C33 H33A . . 108.6 ?
C32 C33 H33B . . 108.6 ?
C34 C33 H33B . . 108.6 ?
H33A C33 H33B . . 107.5 ?
C33 C34 H34A . . 109.5 ?
C33 C34 H34B . . 109.5 ?
H34A C34 H34B . . 109.5 ?
C33 C34 H34C . . 109.5 ?
H34A C34 H34C . . 109.5 ?
H34B C34 H34C . . 109.5 ?
C1 N1 C4 . . 117.4(2) ?
C1 N2 C2 . . 110.3(2) ?
C5 N3 C3 . . 104.00(19) ?
C5 N4 C2 . . 106.35(18) ?
C5 N4 C6 . . 127.05(19) ?
C2 N4 C6 . . 126.5(2) ?
C4 N5 H1N . . 120.1(18) ?
C4 N5 H2N . . 120.5(17) ?
H1N N5 H2N . . 116.(2) ?
C18 N6 C21 . . 120.46(18) ?
C18 N6 C23 . . 119.60(18) ?
C21 N6 C23 . . 119.83(19) ?
C18 N7 C19 . . 127.1(2) ?
C18 N7 H3N . . 116.9(16) ?
C19 N7 H3N . . 115.9(16) ?

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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
N2 C2 C3 N3 . . . . -177.6(2) ?
N4 C2 C3 N3 . . . . 0.7(2) ?
N2 C2 C3 C4 . . . . -1.5(3) ?
N4 C2 C3 C4 . . . . 176.78(18) ?
C2 C3 C4 N5 . . . . -178.2(2) ?
N3 C3 C4 N5 . . . . -3.1(4) ?
C2 C3 C4 N1 . . . . 1.9(3) ?
N3 C3 C4 N1 . . . . 177.0(2) ?
N4 C6 C7 C8 . . . . -62.9(3) ?
C6 C7 C8 C9 . . . . -172.53(19) ?
C7 C8 C9 C10 . . . . -179.6(2) ?
C8 C9 C10 C11 . . . . -177.1(2) ?
C9 C10 C11 C12 . . . . -178.7(2) ?
C10 C11 C12 C13 . . . . -178.5(2) ?
C11 C12 C13 C14 . . . . 180.0(2) ?
C12 C13 C14 C15 . . . . -179.8(2) ?
C13 C14 C15 C16 . . . . 179.4(2) ?
C14 C15 C16 C17 . . . . 179.5(2) ?
O2 C19 C20 C21 . . . . -179.1(2) ?
N7 C19 C20 C21 . . . . 0.6(3) ?
O2 C19 C20 C22 . . . . -0.1(3) ?
N7 C19 C20 C22 . . . . 179.6(2) ?
C19 C20 C21 N6 . . . . -2.1(3) ?
C22 C20 C21 N6 . . . . 178.9(2) ?
N6 C23 C24 C25 . . . . 66.0(3) ?
C23 C24 C25 C26 . . . . 174.93(19) ?
C24 C25 C26 C27 . . . . -178.5(2) ?
C25 C26 C27 C28 . . . . 179.1(2) ?
C26 C27 C28 C29 . . . . 179.3(2) ?
C27 C28 C29 C30 . . . . 179.3(2) ?
C28 C29 C30 C31 . . . . 179.7(2) ?
C29 C30 C31 C32 . . . . 179.1(2) ?
C30 C31 C32 C33 . . . . 179.7(2) ?
C31 C32 C33 C34 . . . . 177.8(2) ?
N2 C1 N1 C4 . . . . 1.3(4) ?
N5 C4 N1 C1 . . . . 178.3(2) ?
C3 C4 N1 C1 . . . . -1.8(3) ?
N1 C1 N2 C2 . . . . -0.8(4) ?
N4 C2 N2 C1 . . . . -177.1(2) ?
C3 C2 N2 C1 . . . . 0.9(3) ?
N4 C5 N3 C3 . . . . 0.0(2) ?
C2 C3 N3 C5 . . . . -0.4(2) ?
C4 C3 N3 C5 . . . . -175.7(2) ?
N3 C5 N4 C2 . . . . 0.4(3) ?
N3 C5 N4 C6 . . . . 177.75(19) ?
N2 C2 N4 C5 . . . . 177.7(2) ?
C3 C2 N4 C5 . . . . -0.6(2) ?
N2 C2 N4 C6 . . . . 0.3(4) ?
C3 C2 N4 C6 . . . . -178.0(2) ?
C7 C6 N4 C5 . . . . 113.7(2) ?
C7 C6 N4 C2 . . . . -69.5(3) ?
O1 C18 N6 C21 . . . . 180.0(2) ?
N7 C18 N6 C21 . . . . 0.2(3) ?
O1 C18 N6 C23 . . . . 3.7(3) ?
N7 C18 N6 C23 . . . . -176.02(18) ?
C20 C21 N6 C18 . . . . 1.7(3) ?
C20 C21 N6 C23 . . . . 178.0(2) ?
C24 C23 N6 C18 . . . . -115.3(2) ?
C24 C23 N6 C21 . . . . 68.5(3) ?
O1 C18 N7 C19 . . . . 178.4(2) ?
N6 C18 N7 C19 . . . . -1.8(3) ?
O2 C19 N7 C18 . . . . -178.9(2) ?
C20 C19 N7 C18 . . . . 1.4(3) ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
N7 H3N N3 . 0.93(3) 1.94(3) 2.867(3) 175.(2) ?
N5 H2N O1 . 0.94(3) 2.01(3) 2.923(3) 164.(2) ?
N5 H1N O2 1_455 0.92(3) 1.99(3) 2.903(3) 170.(3) ?
C6 H6B O1 2_666 0.99 2.53 3.509(3) 169.2 ?
C6 H6B O1 2_666 0.99 2.53 3.509(3) 169.2 ?
N5 H1N O2 1_455 0.92(3) 1.99(3) 2.903(3) 170.(3) ?
N5 H2N O1 . 0.94(3) 2.01(3) 2.923(3) 164.(2) ?
N7 H3N N3 . 0.93(3) 1.94(3) 2.867(3) 175.(2) ?


_exptl_crystal_recrystallization_method 'solvent evaporation'
