##############################################################################
#                                                                            #
# This CIF contains the data in a paper accepted for publication in          #
# Acta Crystallographica Section E. It conforms to the requirements of       #
# Notes for Authors for Acta Crystallographica Section E, and has been       #
# peer reviewed under the auspices of the IUCr Commission on Journals.       #
#                                                                            #
# Full details of the Crystallographic Information File format               #
# are given in the paper "The Crystallographic Information File (CIF):       #
# a New Standard Archive File for Crystallography" by S. R. Hall, F. H.      #
# Allen and I. D. Brown [Acta Cryst. (1991), A47, 655-685].                  #
#                                                                            #
# The current version of the core CIF dictionary is obtainable from          #
# ftp://ftp.iucr.org/pub/cif_core.dic.                                       #
#                                                                            #
# Software is freely available for graphical display of the structure(s)     #
# in this CIF. For information consult the CIF software page                 #
# http://www.iucr.org/resources/cif/software.                                #
#                                                                            #
# This file may be used for bona fide research purposes within the           #
# scientific community so long as proper attribution is given to the journal # 
# article from which it was obtained.                                        #
#                                                                            #
##############################################################################
data_I
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_journal_date_recd_electronic     2020-10-07
_journal_date_accepted     2021-01-05
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2021
_journal_volume     77
_journal_issue      2
_journal_page_first     117
_journal_page_last     120
_journal_paper_category     GO
_journal_paper_doi     10.1107/S2056989021000141
_journal_coeditor_code     DJ2016
_publ_contact_author_name     'Mihaela Cibian'
_publ_contact_author_address
;
Département de Chimie, Biochimie et Physique et l'Institut de Recherche sur
l'Hydrogène (IRH), Université du Québec à Trois-Rivières (UQTR),
3351, boul. des Forges, C.P. 500, Trois-Rivières, QC, G9A 5H7,
Canada
;
_publ_contact_author_email     mihaela.cibian@uqtr.ca
_publ_contact_author_fax     ?
_publ_contact_author_phone     '+1 819 376-5011, 4409'
_publ_section_title
;
N,N'-Bis[2,6-bis(1-methylethyl)phenyl]pyridine-4-carboximidamide
toluene hemisolvate
;
_publ_section_title_footnote     .
loop_
    _publ_author_name
    _publ_author_footnote
    _publ_author_address
    'Cottin, Lola' .
;
Département de Chimie, Biochimie et Physique et l'Institut de Recherche sur
l'Hydrogène (IRH), Université du Québec à Trois-Rivières (UQTR),
3351, Boul. des Forges, C.P. 500, Trois-Rivières, QC, G9A 5H7,
Canada
;
    'Girard, Sarah' .
;
Département de Chimie, Biochimie et Physique et l'Institut de Recherche sur
l'Hydrogène (IRH), Université du Québec à Trois-Rivières (UQTR),
3351, Boul. des Forges, C.P. 500, Trois-Rivières, QC, G9A 5H7,
Canada
;
    'Hanan, Garry S.' .
;
Département de Chimie, Université de Montréal, campus MIL, 1375 Avenue
Thérèse-Lavoie-Roux, Montréal, QC, H2V 0B3,
Canada
;
    'Cibian, Mihaela' .
;
Département de Chimie, Biochimie et Physique et l'Institut de Recherche sur
l'Hydrogène (IRH), Université du Québec à Trois-Rivières (UQTR),
3351, Boul. des Forges, C.P. 500, Trois-Rivières, QC, G9A 5H7,
Canada
;
_publ_section_synopsis
;
A new member of the bulky
N,N'-bis(2,6-diisopropylphenyl)arylamidine family is reported
herein: the N,N'-bis(2,6-diisopropylphenyl)-4-pyridylamidine is
a symmetrically N,N'-disubstituted arylamidine containing a
4-pyridyl substituent on the carbon atom of the N--C--N linkage and bulky
2,6-diisopropylphenyl groups on the nitrogen atoms.
;
_chemical_name_systematic
;
N,N'-Bis[2,6-bis(1-methylethyl)phenyl]pyridine-4-carboximidamide
toluene hemisolvate
;
_chemical_name_common     ?
_chemical_formula_moiety     '2(C30 H39 N3), C7 H8'
_chemical_formula_sum     'C67 H86 N6'
_chemical_formula_iupac     '2C30 H39 N3, C7 H8'
_chemical_formula_weight     975.41
_chemical_melting_point     ?
_space_group_crystal_system     monoclinic
_space_group_name_H-M_alt     'P 1 21/c 1'
_space_group_name_Hall     '-P 2ybc'
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     9.7537(2)
_cell_length_b     20.8030(5)
_cell_length_c     14.7561(4)
_cell_angle_alpha     90
_cell_angle_beta     103.4220(10)
_cell_angle_gamma     90
_cell_volume     2912.33(12)
_cell_formula_units_Z     2
_cell_measurement_reflns_used     9920
_cell_measurement_theta_min     3.74
_cell_measurement_theta_max     71.77
_cell_measurement_temperature     200
_exptl_crystal_description     block
_exptl_crystal_colour     colourless
_exptl_crystal_size_max     0.32
_exptl_crystal_size_mid     0.12
_exptl_crystal_size_min     0.12
_exptl_crystal_density_diffrn     1.112
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     ?
_exptl_crystal_F_000     1060
_exptl_absorpt_coefficient_mu     0.489
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details
;
(SADABS; Bruker, 2014/4)
;
_exptl_absorpt_correction_T_min     0.6288
_exptl_absorpt_correction_T_max     0.7536
_exptl_special_details
;
X-ray crystallographic data for I were collected from a single-crystal sample,
which was mounted on a loop fiber. Data were collected using a Bruker Platform
diffractometer, equipped with a Bruker SMART 4 K Charged-Coupled Device
(CCD) Area Detector using the program APEX2 and a Nonius FR591 rotating
anode equiped with a Montel 200 optics. The crystal-to-detector distance was
5.0 cm, and the data collection was carried out in 512 x 512 pixel
mode. The initial unit-cell parameters were determined by a least-squares fit
of the angular settings of strong reflections, collected by a 10.0 degree scan
in 33 frames over four different parts of the reciprocal space (132 frames
total). One complete sphere of data was collected, to better than 0.80Å
resolution.
;
_diffrn_ambient_temperature     200
_diffrn_source     'rotating-anode with a mirror focussing unit'
_diffrn_radiation_type     CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_monochromator     graphite
_diffrn_measurement_device_type     'Bruker APEXII CCD'
_diffrn_measurement_method     'φ and ω scans'
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     36670
_diffrn_reflns_av_R_equivalents     0.0352
_diffrn_reflns_av_unetI/netI     0.0209
_diffrn_reflns_theta_min     3.741
_diffrn_reflns_theta_max     72.371
_diffrn_reflns_theta_full     67.679
_diffrn_measured_fraction_theta_max     0.981
_diffrn_measured_fraction_theta_full     0.993
_diffrn_reflns_limit_h_min     -11
_diffrn_reflns_limit_h_max     11
_diffrn_reflns_limit_k_min     -25
_diffrn_reflns_limit_k_max     25
_diffrn_reflns_limit_l_min     -15
_diffrn_reflns_limit_l_max     17
_diffrn_standards_number     ?
_diffrn_radiation_probe     x-ray
_refine_special_details     ?
_reflns_number_total     5649
_reflns_number_gt     4950
_reflns_threshold_expression     'I > 2σ(I)'
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0484
_refine_ls_R_factor_gt     0.0434
_refine_ls_wR_factor_gt     0.1149
_refine_ls_wR_factor_ref     0.1198
_refine_ls_goodness_of_fit_ref     1.050
_refine_ls_restrained_S_all     1.023
_refine_ls_number_reflns     5649
_refine_ls_number_parameters     424
_refine_ls_number_restraints     433
_refine_ls_hydrogen_treatment     mixed
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
              'w=1/[σ²(Fo²)+(0.0682P)²+0.4597P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens     mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary     ?
_refine_ls_shift/su_max     0.000
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     0.257
_refine_diff_density_min     -0.203
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef     0.0058(3)
_refine_ls_extinction_expression
                                  'Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^'
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'
_computing_data_collection
;
APEX2 (Bruker, 2007)
;
_computing_cell_refinement
;
SAINT (Bruker, 2009)
;
_computing_data_reduction
;
SAINT (Bruker, 2009)
;
_computing_structure_solution
;
SHELXT (Sheldrick, 2015a)
;
_computing_structure_refinement
;
SHELXL (Sheldrick, 2015b)
;
_computing_molecular_graphics
;
OLEX2 (Dolomanov et al.,  2009)
;
_computing_publication_material
;
OLEX2 (Dolomanov et al.,  2009), ORTEP-3 for Windows
(Farrugia, 2012),
pubCIF (Westrip, 2010), POV-RAY (Povray, 2013), PLATON (Spek,
2020),
Mercury (Macrae et al.,  2020)
;
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_occupancy
    _atom_site_disorder_assembly
    _atom_site_disorder_group
    N N1 0.53487(9) 0.28098(4) 0.39210(6) 0.0314(2) Uani d 1 . .
    N N2 0.76154(9) 0.28020(4) 0.36187(6) 0.0303(2) Uani d 1 . .
    N N3 0.51539(11) 0.15891(5) 0.08225(7) 0.0432(3) Uani d 1 . .
    C C1 0.63027(10) 0.26479(5) 0.34104(7) 0.0278(2) Uani d 1 . .
    C C2 0.58249(11) 0.22664(5) 0.25252(7) 0.0293(2) Uani d 1 . .
    C C3 0.67636(11) 0.18300(5) 0.22828(8) 0.0347(2) Uani d 1 . .
    H H3 0.7655 0.1754 0.2693 0.042 Uiso calc 1 . .
    C C4 0.63893(13) 0.15082(6) 0.14405(8) 0.0403(3) Uani d 1 . .
    H H4 0.7046 0.1212 0.1291 0.048 Uiso calc 1 . .
    C C5 0.42520(13) 0.20012(6) 0.10671(8) 0.0412(3) Uani d 1 . .
    H H5 0.3364 0.2063 0.0646 0.049 Uiso calc 1 . .
    C C6 0.45284(11) 0.23457(6) 0.18962(7) 0.0353(2) Uani d 1 . .
    H H6 0.3843 0.2631 0.2033 0.042 Uiso calc 1 . .
    C C7 0.38815(11) 0.26451(5) 0.37550(7) 0.0325(2) Uani d 1 . .
    C C8 0.34635(12) 0.20029(6) 0.38124(8) 0.0380(3) Uani d 1 . .
    C C9 0.20106(14) 0.18795(7) 0.36374(9) 0.0500(3) Uani d 1 . .
    H H9 0.1695 0.1448 0.3649 0.060 Uiso calc 1 . .
    C C10 0.10303(13) 0.23682(8) 0.34497(10) 0.0542(4) Uani d 1 . .
    H H10 0.0053 0.2271 0.3332 0.065 Uiso calc 1 . .
    C C11 0.14653(13) 0.29971(7) 0.34320(9) 0.0478(3) Uani d 1 . .
    H H11 0.0783 0.3331 0.3321 0.057 Uiso calc 1 . .
    C C12 0.28919(12) 0.31517(6) 0.35745(7) 0.0379(3) Uani d 1 . .
    C C13 0.44931(14) 0.14485(6) 0.40914(9) 0.0433(3) Uani d 1 . .
    H H13 0.5466 0.1617 0.4131 0.052 Uiso calc 1 . .
    C C14 0.44272(17) 0.11946(7) 0.50602(10) 0.0567(4) Uani d 1 . .
    H H14A 0.4637 0.1545 0.5515 0.085 Uiso calc 1 . .
    H H14B 0.5122 0.0850 0.5244 0.085 Uiso calc 1 . .
    H H14C 0.3481 0.1027 0.5038 0.085 Uiso calc 1 . .
    C C15 0.42194(18) 0.09041(7) 0.33691(12) 0.0610(4) Uani d 1 . .
    H H15A 0.3273 0.0728 0.3322 0.092 Uiso calc 1 . .
    H H15B 0.4921 0.0564 0.3563 0.092 Uiso calc 1 . .
    H H15C 0.4290 0.1073 0.2761 0.092 Uiso calc 1 . .
    C C16 0.33464(13) 0.38487(6) 0.35151(9) 0.0440(3) Uani d 1 . .
    H H16 0.4341 0.3883 0.3886 0.053 Uiso calc 1 . .
    C C17 0.2473(2) 0.43221(10) 0.39327(18) 0.0935(7) Uani d 1 . .
    H H17A 0.1518 0.4346 0.3535 0.140 Uiso calc 1 . .
    H H17B 0.2912 0.4748 0.3975 0.140 Uiso calc 1 . .
    H H17C 0.2426 0.4177 0.4557 0.140 Uiso calc 1 . .
    C C18 0.3345(2) 0.40341(8) 0.25163(11) 0.0725(5) Uani d 1 . .
    H H18A 0.3964 0.3742 0.2274 0.109 Uiso calc 1 . .
    H H18B 0.3685 0.4476 0.2503 0.109 Uiso calc 1 . .
    H H18C 0.2384 0.4003 0.2129 0.109 Uiso calc 1 . .
    C C19 0.82379(10) 0.31763(5) 0.44194(7) 0.0299(2) Uani d 1 . .
    C C20 0.90785(11) 0.28642(5) 0.52053(8) 0.0340(2) Uani d 1 . .
    C C21 0.98604(13) 0.32403(6) 0.59266(8) 0.0423(3) Uani d 1 . .
    H H21 1.0435 0.3036 0.6457 0.051 Uiso calc 1 . .
    C C22 0.98145(13) 0.39049(6) 0.58836(9) 0.0457(3) Uani d 1 . .
    H H22 1.0365 0.4153 0.6376 0.055 Uiso calc 1 . .
    C C23 0.89641(13) 0.42074(6) 0.51204(9) 0.0416(3) Uani d 1 . .
    H H23 0.8926 0.4664 0.5101 0.050 Uiso calc 1 . .
    C C24 0.81617(11) 0.38542(5) 0.43795(8) 0.0346(3) Uani d 1 . .
    C C25 0.90836(13) 0.21355(6) 0.52829(8) 0.0398(3) Uani d 1 . .
    H H25 0.8783 0.1956 0.4638 0.048 Uiso calc 1 . .
    C C26 0.79988(16) 0.19247(6) 0.58252(11) 0.0531(3) Uani d 1 . .
    H H26A 0.8285 0.2082 0.6467 0.080 Uiso calc 1 . .
    H H26B 0.7944 0.1454 0.5828 0.080 Uiso calc 1 . .
    H H26C 0.7074 0.2103 0.5527 0.080 Uiso calc 1 . .
    C C27 1.05315(15) 0.18549(7) 0.57291(10) 0.0542(4) Uani d 1 . .
    H H27A 1.1228 0.2017 0.5402 0.081 Uiso calc 1 . .
    H H27B 1.0490 0.1385 0.5686 0.081 Uiso calc 1 . .
    H H27C 1.0804 0.1983 0.6385 0.081 Uiso calc 1 . .
    C C28 0.72676(13) 0.41935(6) 0.35301(9) 0.0411(3) Uani d 1 . .
    H H28 0.6473 0.3899 0.3247 0.049 Uiso calc 1 . .
    C C29 0.66220(16) 0.48254(6) 0.37642(11) 0.0559(4) Uani d 1 . .
    H H29A 0.6139 0.4752 0.4268 0.084 Uiso calc 1 . .
    H H29B 0.5944 0.4983 0.3211 0.084 Uiso calc 1 . .
    H H29C 0.7370 0.5145 0.3963 0.084 Uiso calc 1 . .
    C C30 0.81250(17) 0.43109(7) 0.27984(10) 0.0579(4) Uani d 1 . .
    H H30A 0.8904 0.4606 0.3051 0.087 Uiso calc 1 . .
    H H30B 0.7516 0.4500 0.2240 0.087 Uiso calc 1 . .
    H H30C 0.8504 0.3902 0.2636 0.087 Uiso calc 1 . .
    C C37B 1.0818(16) -0.0445(6) 0.6520(6) 0.112(4) Uani d 0.25 A -1
    H H37A 1.0328 -0.0847 0.6587 0.168 Uiso calc 0.25 A -1
    H H37B 1.0700 -0.0142 0.7004 0.168 Uiso calc 0.25 A -1
    H H37C 1.1823 -0.0532 0.6583 0.168 Uiso calc 0.25 A -1
    C C31B 1.0211(9) -0.0160(4) 0.5579(5) 0.080(3) Uani d 0.25 A -1
    C C32B 0.8827(9) 0.0063(6) 0.5345(6) 0.079(4) Uani d 0.25 A -1
    H H32B 0.8254 0.0024 0.5782 0.095 Uiso calc 0.25 A -1
    C C33B 0.8272(9) 0.0339(6) 0.4482(7) 0.084(4) Uani d 0.25 A -1
    H H33B 0.7326 0.0490 0.4334 0.101 Uiso calc 0.25 A -1
    C C34B 0.9093(13) 0.0397(4) 0.3836(5) 0.088(4) Uani d 0.25 A -1
    H H34B 0.8715 0.0587 0.3245 0.105 Uiso calc 0.25 A -1
    C C35B 1.0473(13) 0.0176(4) 0.4059(6) 0.093(4) Uani d 0.25 A -1
    H H35B 1.1043 0.0215 0.3620 0.111 Uiso calc 0.25 A -1
    C C36B 1.1022(8) -0.0100(4) 0.4922(7) 0.090(4) Uani d 0.25 A -1
    H H36B 1.1966 -0.0251 0.5067 0.109 Uiso calc 0.25 A -1
    C C31A 1.0600(10) -0.0150(4) 0.5303(7) 0.065(2) Uani d 0.25 B -2
    C C32A 0.9297(14) -0.0029(7) 0.5489(10) 0.070(4) Uani d 0.25 B -2
    H H32A 0.9145 -0.0139 0.6083 0.084 Uiso calc 0.25 B -2
    C C33A 0.8199(12) 0.0251(6) 0.4829(10) 0.080(3) Uani d 0.25 B -2
    H H33A 0.7296 0.0310 0.4957 0.096 Uiso calc 0.25 B -2
    C C34A 0.8457(13) 0.0441(11) 0.3983(11) 0.073(3) Uani d 0.25 B -2
    H H34A 0.7763 0.0675 0.3549 0.088 Uiso calc 0.25 B -2
    C C35A 0.9736(11) 0.0288(6) 0.3772(8) 0.074(3) Uani d 0.25 B -2
    H H35A 0.9873 0.0379 0.3168 0.089 Uiso calc 0.25 B -2
    C C36A 1.0805(13) 0.0008(8) 0.4423(9) 0.060(3) Uani d 0.25 B -2
    H H36A 1.1685 -0.0078 0.4276 0.072 Uiso calc 0.25 B -2
    C C37A 1.1873(16) -0.0441(10) 0.5950(11) 0.082(4) Uani d 0.25 B -2
    H H37D 1.1802 -0.0383 0.6596 0.122 Uiso calc 0.25 B -2
    H H37E 1.2727 -0.0228 0.5858 0.122 Uiso calc 0.25 B -2
    H H37F 1.1918 -0.0901 0.5816 0.122 Uiso calc 0.25 B -2
    H H1 0.5679(14) 0.3064(6) 0.4406(10) 0.039(3) Uiso 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
    N1 C1 . 1.3682(13) ?
    N1 C7 . 1.4362(13) ?
    N1 H1 . 0.888(14) ?
    N2 C1 . 1.2861(13) ?
    N2 C19 . 1.4275(13) ?
    N3 C4 . 1.3423(16) ?
    N3 C5 . 1.3367(16) ?
    C1 C2 . 1.5069(14) ?
    C2 C3 . 1.3938(15) ?
    C2 C6 . 1.3939(15) ?
    C3 H3 . 0.9500 ?
    C3 C4 . 1.3841(16) ?
    C4 H4 . 0.9500 ?
    C5 H5 . 0.9500 ?
    C5 C6 . 1.3891(16) ?
    C6 H6 . 0.9500 ?
    C7 C8 . 1.4051(16) ?
    C7 C12 . 1.4120(16) ?
    C8 C9 . 1.4039(17) ?
    C8 C13 . 1.5218(18) ?
    C9 H9 . 0.9500 ?
    C9 C10 . 1.379(2) ?
    C10 H10 . 0.9500 ?
    C10 C11 . 1.377(2) ?
    C11 H11 . 0.9500 ?
    C11 C12 . 1.3957(17) ?
    C12 C16 . 1.5249(18) ?
    C13 H13 . 1.0000 ?
    C13 C14 . 1.5394(19) ?
    C13 C15 . 1.5356(18) ?
    C14 H14A . 0.9800 ?
    C14 H14B . 0.9800 ?
    C14 H14C . 0.9800 ?
    C15 H15A . 0.9800 ?
    C15 H15B . 0.9800 ?
    C15 H15C . 0.9800 ?
    C16 H16 . 1.0000 ?
    C16 C17 . 1.523(2) ?
    C16 C18 . 1.523(2) ?
    C17 H17A . 0.9800 ?
    C17 H17B . 0.9800 ?
    C17 H17C . 0.9800 ?
    C18 H18A . 0.9800 ?
    C18 H18B . 0.9800 ?
    C18 H18C . 0.9800 ?
    C19 C20 . 1.4133(15) ?
    C19 C24 . 1.4127(15) ?
    C20 C21 . 1.3963(16) ?
    C20 C25 . 1.5203(16) ?
    C21 H21 . 0.9500 ?
    C21 C22 . 1.3843(19) ?
    C22 H22 . 0.9500 ?
    C22 C23 . 1.3851(18) ?
    C23 H23 . 0.9500 ?
    C23 C24 . 1.3966(16) ?
    C24 C28 . 1.5239(16) ?
    C25 H25 . 1.0000 ?
    C25 C26 . 1.5314(19) ?
    C25 C27 . 1.5286(17) ?
    C26 H26A . 0.9800 ?
    C26 H26B . 0.9800 ?
    C26 H26C . 0.9800 ?
    C27 H27A . 0.9800 ?
    C27 H27B . 0.9800 ?
    C27 H27C . 0.9800 ?
    C28 H28 . 1.0000 ?
    C28 C29 . 1.5312(18) ?
    C28 C30 . 1.5311(19) ?
    C29 H29A . 0.9800 ?
    C29 H29B . 0.9800 ?
    C29 H29C . 0.9800 ?
    C30 H30A . 0.9800 ?
    C30 H30B . 0.9800 ?
    C30 H30C . 0.9800 ?
    C37B H37A . 0.9800 ?
    C37B H37B . 0.9800 ?
    C37B H37C . 0.9800 ?
    C37B C31B . 1.4987 ?
    C31B C32B . 1.3924 ?
    C31B C36B . 1.3918 ?
    C32B H32B . 0.9500 ?
    C32B C33B . 1.3872 ?
    C33B H33B . 0.9500 ?
    C33B C34B . 1.3864 ?
    C34B H34B . 0.9500 ?
    C34B C35B . 1.3871 ?
    C35B H35B . 0.9500 ?
    C35B C36B . 1.3872 ?
    C36B H36B . 0.9500 ?
    C31A C32A . 1.384(10) ?
    C31A C36A . 1.398(10) ?
    C31A C37A . 1.506(11) ?
    C32A H32A . 0.9500 ?
    C32A C33A . 1.397(10) ?
    C33A H33A . 0.9500 ?
    C33A C34A . 1.388(10) ?
    C34A H34A . 0.9500 ?
    C34A C35A . 1.391(10) ?
    C35A H35A . 0.9500 ?
    C35A C36A . 1.373(10) ?
    C36A H36A . 0.9500 ?
    C37A H37D . 0.9800 ?
    C37A H37E . 0.9800 ?
    C37A H37F . 0.9800 ?
loop_
    _geom_contact_atom_site_label_1
    _geom_contact_atom_site_label_2
    _geom_contact_distance
    _geom_contact_site_symmetry_1
    _geom_contact_site_symmetry_2
    _geom_contact_publ_flag
    ? ? ? ? ? ?
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
    C1 N1 C7 . . 128.72(9) ?
    C1 N1 H1 . . 115.1(9) ?
    C7 N1 H1 . . 116.1(9) ?
    C1 N2 C19 . . 122.84(9) ?
    C5 N3 C4 . . 116.11(10) ?
    N1 C1 C2 . . 119.60(9) ?
    N2 C1 N1 . . 125.01(9) ?
    N2 C1 C2 . . 115.39(9) ?
    C3 C2 C1 . . 118.44(9) ?
    C3 C2 C6 . . 117.04(10) ?
    C6 C2 C1 . . 124.41(9) ?
    C2 C3 H3 . . 120.2 ?
    C4 C3 C2 . . 119.57(10) ?
    C4 C3 H3 . . 120.2 ?
    N3 C4 C3 . . 123.89(11) ?
    N3 C4 H4 . . 118.1 ?
    C3 C4 H4 . . 118.1 ?
    N3 C5 H5 . . 117.9 ?
    N3 C5 C6 . . 124.29(11) ?
    C6 C5 H5 . . 117.9 ?
    C2 C6 H6 . . 120.5 ?
    C5 C6 C2 . . 119.08(10) ?
    C5 C6 H6 . . 120.5 ?
    C8 C7 N1 . . 120.54(10) ?
    C8 C7 C12 . . 121.72(10) ?
    C12 C7 N1 . . 117.69(10) ?
    C7 C8 C13 . . 123.67(10) ?
    C9 C8 C7 . . 117.22(12) ?
    C9 C8 C13 . . 119.06(11) ?
    C8 C9 H9 . . 119.2 ?
    C10 C9 C8 . . 121.69(13) ?
    C10 C9 H9 . . 119.2 ?
    C9 C10 H10 . . 119.9 ?
    C11 C10 C9 . . 120.12(12) ?
    C11 C10 H10 . . 119.9 ?
    C10 C11 H11 . . 119.4 ?
    C10 C11 C12 . . 121.11(13) ?
    C12 C11 H11 . . 119.4 ?
    C7 C12 C16 . . 121.70(10) ?
    C11 C12 C7 . . 118.06(12) ?
    C11 C12 C16 . . 120.23(11) ?
    C8 C13 H13 . . 108.0 ?
    C8 C13 C14 . . 110.13(11) ?
    C8 C13 C15 . . 111.95(11) ?
    C14 C13 H13 . . 108.0 ?
    C15 C13 H13 . . 108.0 ?
    C15 C13 C14 . . 110.70(11) ?
    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 ?
    C13 C15 H15A . . 109.5 ?
    C13 C15 H15B . . 109.5 ?
    C13 C15 H15C . . 109.5 ?
    H15A C15 H15B . . 109.5 ?
    H15A C15 H15C . . 109.5 ?
    H15B C15 H15C . . 109.5 ?
    C12 C16 H16 . . 107.1 ?
    C17 C16 C12 . . 113.21(13) ?
    C17 C16 H16 . . 107.1 ?
    C18 C16 C12 . . 111.19(10) ?
    C18 C16 H16 . . 107.1 ?
    C18 C16 C17 . . 110.66(15) ?
    C16 C17 H17A . . 109.5 ?
    C16 C17 H17B . . 109.5 ?
    C16 C17 H17C . . 109.5 ?
    H17A C17 H17B . . 109.5 ?
    H17A C17 H17C . . 109.5 ?
    H17B C17 H17C . . 109.5 ?
    C16 C18 H18A . . 109.5 ?
    C16 C18 H18B . . 109.5 ?
    C16 C18 H18C . . 109.5 ?
    H18A C18 H18B . . 109.5 ?
    H18A C18 H18C . . 109.5 ?
    H18B C18 H18C . . 109.5 ?
    C20 C19 N2 . . 118.87(9) ?
    C24 C19 N2 . . 120.13(9) ?
    C24 C19 C20 . . 120.51(10) ?
    C19 C20 C25 . . 120.74(9) ?
    C21 C20 C19 . . 118.57(11) ?
    C21 C20 C25 . . 120.64(10) ?
    C20 C21 H21 . . 119.4 ?
    C22 C21 C20 . . 121.24(11) ?
    C22 C21 H21 . . 119.4 ?
    C21 C22 H22 . . 120.1 ?
    C21 C22 C23 . . 119.86(11) ?
    C23 C22 H22 . . 120.1 ?
    C22 C23 H23 . . 119.4 ?
    C22 C23 C24 . . 121.23(11) ?
    C24 C23 H23 . . 119.4 ?
    C19 C24 C28 . . 120.75(10) ?
    C23 C24 C19 . . 118.56(10) ?
    C23 C24 C28 . . 120.66(10) ?
    C20 C25 H25 . . 107.7 ?
    C20 C25 C26 . . 109.53(10) ?
    C20 C25 C27 . . 113.56(10) ?
    C26 C25 H25 . . 107.7 ?
    C27 C25 H25 . . 107.7 ?
    C27 C25 C26 . . 110.30(11) ?
    C25 C26 H26A . . 109.5 ?
    C25 C26 H26B . . 109.5 ?
    C25 C26 H26C . . 109.5 ?
    H26A C26 H26B . . 109.5 ?
    H26A C26 H26C . . 109.5 ?
    H26B C26 H26C . . 109.5 ?
    C25 C27 H27A . . 109.5 ?
    C25 C27 H27B . . 109.5 ?
    C25 C27 H27C . . 109.5 ?
    H27A C27 H27B . . 109.5 ?
    H27A C27 H27C . . 109.5 ?
    H27B C27 H27C . . 109.5 ?
    C24 C28 H28 . . 107.5 ?
    C24 C28 C29 . . 113.51(11) ?
    C24 C28 C30 . . 110.60(10) ?
    C29 C28 H28 . . 107.5 ?
    C30 C28 H28 . . 107.5 ?
    C30 C28 C29 . . 110.05(11) ?
    C28 C29 H29A . . 109.5 ?
    C28 C29 H29B . . 109.5 ?
    C28 C29 H29C . . 109.5 ?
    H29A C29 H29B . . 109.5 ?
    H29A C29 H29C . . 109.5 ?
    H29B C29 H29C . . 109.5 ?
    C28 C30 H30A . . 109.5 ?
    C28 C30 H30B . . 109.5 ?
    C28 C30 H30C . . 109.5 ?
    H30A C30 H30B . . 109.5 ?
    H30A C30 H30C . . 109.5 ?
    H30B C30 H30C . . 109.5 ?
    H37A C37B H37B . . 109.5 ?
    H37A C37B H37C . . 109.5 ?
    H37B C37B H37C . . 109.5 ?
    C31B C37B H37A . . 109.5 ?
    C31B C37B H37B . . 109.5 ?
    C31B C37B H37C . . 109.5 ?
    C32B C31B C37B . . 120.9 ?
    C36B C31B C37B . . 120.9 ?
    C36B C31B C32B . . 118.1 ?
    C31B C32B H32B . . 119.5 ?
    C33B C32B C31B . . 121.1 ?
    C33B C32B H32B . . 119.5 ?
    C32B C33B H33B . . 119.9 ?
    C34B C33B C32B . . 120.1 ?
    C34B C33B H33B . . 119.9 ?
    C33B C34B H34B . . 120.3 ?
    C33B C34B C35B . . 119.5 ?
    C35B C34B H34B . . 120.3 ?
    C34B C35B H35B . . 119.9 ?
    C34B C35B C36B . . 120.1 ?
    C36B C35B H35B . . 119.9 ?
    C31B C36B H36B . . 119.5 ?
    C35B C36B C31B . . 121.1 ?
    C35B C36B H36B . . 119.5 ?
    C32A C31A C36A . . 118.5(9) ?
    C32A C31A C37A . . 127.4(9) ?
    C36A C31A C37A . . 114.1(8) ?
    C31A C32A H32A . . 119.1 ?
    C31A C32A C33A . . 121.9(10) ?
    C33A C32A H32A . . 119.1 ?
    C32A C33A H33A . . 120.8 ?
    C34A C33A C32A . . 118.4(10) ?
    C34A C33A H33A . . 120.8 ?
    C33A C34A H34A . . 120.1 ?
    C33A C34A C35A . . 119.7(10) ?
    C35A C34A H34A . . 120.1 ?
    C34A C35A H35A . . 119.5 ?
    C36A C35A C34A . . 121.0(10) ?
    C36A C35A H35A . . 119.5 ?
    C31A C36A H36A . . 120.0 ?
    C35A C36A C31A . . 120.0(10) ?
    C35A C36A H36A . . 120.0 ?
    C31A C37A H37D . . 109.5 ?
    C31A C37A H37E . . 109.5 ?
    C31A C37A H37F . . 109.5 ?
    H37D C37A H37E . . 109.5 ?
    H37D C37A H37F . . 109.5 ?
    H37E C37A H37F . . 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_site_symmetry_1
    _geom_torsion_site_symmetry_2
    _geom_torsion_site_symmetry_3
    _geom_torsion_site_symmetry_4
    _geom_torsion
    _geom_torsion_publ_flag
    N1 C1 C2 C3 . . . . -146.50(10) ?
    N1 C1 C2 C6 . . . . 37.47(15) ?
    N1 C7 C8 C9 . . . . -179.75(10) ?
    N1 C7 C8 C13 . . . . 2.96(16) ?
    N1 C7 C12 C11 . . . . -178.67(10) ?
    N1 C7 C12 C16 . . . . 2.54(15) ?
    N2 C1 C2 C3 . . . . 34.15(13) ?
    N2 C1 C2 C6 . . . . -141.88(11) ?
    N2 C19 C20 C21 . . . . 170.13(10) ?
    N2 C19 C20 C25 . . . . -12.43(15) ?
    N2 C19 C24 C23 . . . . -170.09(10) ?
    N2 C19 C24 C28 . . . . 7.60(15) ?
    N3 C5 C6 C2 . . . . 0.18(19) ?
    C1 N1 C7 C8 . . . . 65.88(15) ?
    C1 N1 C7 C12 . . . . -116.81(12) ?
    C1 N2 C19 C20 . . . . 103.81(12) ?
    C1 N2 C19 C24 . . . . -84.22(13) ?
    C1 C2 C3 C4 . . . . -175.29(10) ?
    C1 C2 C6 C5 . . . . 174.92(10) ?
    C2 C3 C4 N3 . . . . 0.11(19) ?
    C3 C2 C6 C5 . . . . -1.16(16) ?
    C4 N3 C5 C6 . . . . 0.93(19) ?
    C5 N3 C4 C3 . . . . -1.08(19) ?
    C6 C2 C3 C4 . . . . 1.03(16) ?
    C7 N1 C1 N2 . . . . -178.19(10) ?
    C7 N1 C1 C2 . . . . 2.53(16) ?
    C7 C8 C9 C10 . . . . -2.29(18) ?
    C7 C8 C13 C14 . . . . 109.96(13) ?
    C7 C8 C13 C15 . . . . -126.43(12) ?
    C7 C12 C16 C17 . . . . -142.62(14) ?
    C7 C12 C16 C18 . . . . 92.07(14) ?
    C8 C7 C12 C11 . . . . -1.39(16) ?
    C8 C7 C12 C16 . . . . 179.82(10) ?
    C8 C9 C10 C11 . . . . -0.1(2) ?
    C9 C8 C13 C14 . . . . -67.28(14) ?
    C9 C8 C13 C15 . . . . 56.33(15) ?
    C9 C10 C11 C12 . . . . 1.9(2) ?
    C10 C11 C12 C7 . . . . -1.16(18) ?
    C10 C11 C12 C16 . . . . 177.65(11) ?
    C11 C12 C16 C17 . . . . 38.62(18) ?
    C11 C12 C16 C18 . . . . -86.69(15) ?
    C12 C7 C8 C9 . . . . 3.05(16) ?
    C12 C7 C8 C13 . . . . -174.24(10) ?
    C13 C8 C9 C10 . . . . 175.13(12) ?
    C19 N2 C1 N1 . . . . -0.92(16) ?
    C19 N2 C1 C2 . . . . 178.39(9) ?
    C19 C20 C21 C22 . . . . 0.43(18) ?
    C19 C20 C25 C26 . . . . -93.53(13) ?
    C19 C20 C25 C27 . . . . 142.67(11) ?
    C19 C24 C28 C29 . . . . 147.41(11) ?
    C19 C24 C28 C30 . . . . -88.34(13) ?
    C20 C19 C24 C23 . . . . 1.76(16) ?
    C20 C19 C24 C28 . . . . 179.45(10) ?
    C20 C21 C22 C23 . . . . 0.99(19) ?
    C21 C20 C25 C26 . . . . 83.85(14) ?
    C21 C20 C25 C27 . . . . -39.94(16) ?
    C21 C22 C23 C24 . . . . -1.05(19) ?
    C22 C23 C24 C19 . . . . -0.32(17) ?
    C22 C23 C24 C28 . . . . -178.01(11) ?
    C23 C24 C28 C29 . . . . -34.95(16) ?
    C23 C24 C28 C30 . . . . 89.31(14) ?
    C24 C19 C20 C21 . . . . -1.81(16) ?
    C24 C19 C20 C25 . . . . 175.62(10) ?
    C25 C20 C21 C22 . . . . -177.01(12) ?
    C37B C31B C32B C33B . . . . 178.5 ?
    C37B C31B C36B C35B . . . . -178.5 ?
    C31B C32B C33B C34B . . . . 0.2 ?
    C32B C31B C36B C35B . . . . 0.4 ?
    C32B C33B C34B C35B . . . . 0.0 ?
    C33B C34B C35B C36B . . . . 0.0 ?
    C34B C35B C36B C31B . . . . -0.2 ?
    C36B C31B C32B C33B . . . . -0.3 ?
    C31A C32A C33A C34A . . . . -3.4(17) ?
    C32A C31A C36A C35A . . . . 1(2) ?
    C32A C33A C34A C35A . . . . 7(2) ?
    C33A C34A C35A C36A . . . . -7(3) ?
    C34A C35A C36A C31A . . . . 2(2) ?
    C36A C31A C32A C33A . . . . -0.7(18) ?
    C37A C31A C32A C33A . . . . 179.2(14) ?
    C37A C31A C36A C35A . . . . -178.7(15) ?
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
    N1 H1 N3 4_566 0.890(10)
                           2.380(10)
                                   3.1180(10)
                                            141.0(10)
    C10 H10 N2 1_455 0.95 2.74 3.515(2) 139
    C13 H13 N1 . 1.00 2.50 2.9794(15) 109
    C16 H16 N1 . 1.00 2.44 2.8811(15) 106
    C25 H25 N2 . 1.00 2.42 2.8933(15) 108
    C28 H28 N2 . 1.00 2.54 2.9140(15) 102
_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.
;
_shelx_estimated_absorpt_T_min     0.859
_shelx_estimated_absorpt_T_max     0.944
_shelxl_version_number     2014/6
