2,13-Dibenzyl-5,16-diethyl-2,6,13,17-tetra-aza-tricyclo-[16.4.0.0]docosan-2-ium nitrate.

One of the tertiary amine atoms has been protonated in the title salt, C(36)H(57)N(4) (+)·NO(3) (-). The four N atoms of the macrocycle are almost coplanar (r.m.s. deviation = 0.0053 Å), a result correlated with the formation of intra-molecular N-H⋯N and N-H⋯(N,N) hydrogen bonds. With respect to this plane, the benzyl groups lie to either side; a similar arrangement pertains for the cyclo-hexyl rings (each with a chair conformation). Helical supra-molecular chains are evident in the crystal, whereby alternating cations and anions are linked by C-H⋯O inter-actions. The chains are consolidated into supra-molecular arrays in the ab plane via C-H⋯π contacts involving both benzene rings.

Related literature

For the synthesis of the precursor macrocycle, see: Lim et al. (2006 ▶); For related structures, see: Choi et al. (2006 ▶, 2010a ▶,b ▶).

Experimental

Crystal data

C36H57N4 +·NO3 −

M = 607.87

Monoclinic,

a = 10.7882 (1) Å

b = 16.2785 (1) Å

c = 19.0962 (1) Å

β = 98.2461 (6)°

V = 3318.92 (4) Å3

Z = 4

Cu Kα radiation

μ = 0.61 mm−1

T = 100 K

0.30 × 0.20 × 0.10 mm

Data collection

Agilent SuperNova Dual diffractometer with an Atlas detector

Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010 ▶) T min = 0.839, T max = 0.942

24730 measured reflections

6689 independent reflections

6289 reflections with I > 2σ(I)

R int = 0.040

Refinement

R[F 2 > 2σ(F 2)] = 0.039

wR(F 2) = 0.120

S = 1.06

6689 reflections

409 parameters

3 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.31 e Å−3

Δρmin = −0.25 e Å−3

Data collection: CrysAlis PRO (Agilent, 2010 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶) and DIAMOND (Brandenburg, 2006 ▶); software used to prepare material for publication: publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811029692/hb6328sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811029692/hb6328Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811029692/hb6328Isup3.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C36H57N4+·NO3−	F(000) = 1328
Mr = 607.87	Dx = 1.217 Mg m−3
Monoclinic, P21/n	Cu Kα radiation, λ = 1.54184 Å
Hall symbol: -P 2yn	Cell parameters from 15422 reflections
a = 10.7882 (1) Å	θ = 2.7–74.2°
b = 16.2785 (1) Å	µ = 0.61 mm−1
c = 19.0962 (1) Å	T = 100 K
β = 98.2461 (6)°	Prism, colorless
V = 3318.92 (4) Å3	0.30 × 0.20 × 0.10 mm
Z = 4

Agilent SuperNova Dual diffractometer with an Atlas detector	6689 independent reflections
Radiation source: SuperNova (Cu) X-ray Source	6289 reflections with I > 2σ(I)
Mirror	Rint = 0.040
Detector resolution: 10.4041 pixels mm-1	θmax = 74.4°, θmin = 3.6°
ω scans	h = −13→13
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010)	k = −20→20
Tmin = 0.839, Tmax = 0.942	l = −23→23
24730 measured reflections

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.039	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.120	H atoms treated by a mixture of independent and constrained refinement
S = 1.06	w = 1/[σ2(Fo2) + (0.0639P)2 + 0.9655P] where P = (Fo2 + 2Fc2)/3
6689 reflections	(Δ/σ)max = 0.001
409 parameters	Δρmax = 0.31 e Å−3
3 restraints	Δρmin = −0.25 e Å−3

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

	x	y	z	Uiso*/Ueq
O1	0.50228 (8)	0.10547 (5)	0.24392 (5)	0.0332 (2)
O2	0.56328 (8)	−0.01583 (6)	0.28070 (5)	0.0327 (2)
O3	0.39115 (8)	−0.00135 (5)	0.20754 (4)	0.02779 (19)
N1	0.43505 (7)	0.37105 (5)	0.22433 (4)	0.01185 (17)
N2	0.57885 (7)	0.45766 (5)	0.32911 (4)	0.01289 (18)
N3	0.56192 (7)	0.62777 (5)	0.27861 (4)	0.01193 (17)
N4	0.41868 (7)	0.53381 (5)	0.17396 (4)	0.01209 (17)
N5	0.48585 (8)	0.02911 (6)	0.24405 (5)	0.0209 (2)
C1	0.52521 (9)	0.30042 (6)	0.22417 (5)	0.0158 (2)
H1A	0.4785	0.2479	0.2221	0.019*
H1B	0.5853	0.3011	0.2685	0.019*
C2	0.59572 (9)	0.30616 (6)	0.16165 (5)	0.0148 (2)
C3	0.69049 (9)	0.36427 (6)	0.16127 (5)	0.0176 (2)
H3A	0.7107	0.4000	0.2006	0.021*
C4	0.75561 (10)	0.37032 (7)	0.10379 (6)	0.0207 (2)
H4A	0.8200	0.4101	0.1037	0.025*
C5	0.72593 (10)	0.31770 (7)	0.04624 (5)	0.0212 (2)
H5	0.7700	0.3218	0.0067	0.025*
C6	0.63240 (10)	0.25951 (7)	0.04648 (5)	0.0205 (2)
H6	0.6127	0.2236	0.0072	0.025*
C7	0.56721 (9)	0.25352 (7)	0.10399 (5)	0.0175 (2)
H7	0.5031	0.2135	0.1040	0.021*
C8	0.33318 (9)	0.36493 (6)	0.16142 (5)	0.0138 (2)
H8A	0.2848	0.3140	0.1659	0.017*
H8B	0.3729	0.3601	0.1180	0.017*
C9	0.24291 (9)	0.43716 (6)	0.15289 (5)	0.0135 (2)
H9A	0.2132	0.4475	0.1988	0.016*
H9B	0.1691	0.4220	0.1183	0.016*
C10	0.29874 (9)	0.51689 (6)	0.12824 (5)	0.0129 (2)
H10	0.3172	0.5080	0.0790	0.015*
C11	0.20492 (9)	0.58771 (6)	0.12639 (5)	0.0171 (2)
H11A	0.1853	0.5968	0.1749	0.020*
H11B	0.2448	0.6383	0.1116	0.020*
C12	0.08247 (10)	0.57368 (8)	0.07684 (6)	0.0254 (3)
H12A	0.0277	0.6215	0.0785	0.038*
H12B	0.0407	0.5246	0.0919	0.038*
H12C	0.1004	0.5660	0.0284	0.038*
C13	0.49956 (9)	0.59796 (6)	0.14997 (5)	0.0125 (2)
H13	0.4500	0.6496	0.1400	0.015*
C14	0.55226 (9)	0.57130 (6)	0.08313 (5)	0.0162 (2)
H14A	0.4824	0.5636	0.0440	0.019*
H14B	0.5959	0.5180	0.0919	0.019*
C15	0.64389 (10)	0.63526 (7)	0.06136 (5)	0.0192 (2)
H15A	0.6804	0.6146	0.0201	0.023*
H15B	0.5979	0.6866	0.0471	0.023*
C16	0.74889 (9)	0.65372 (7)	0.12163 (5)	0.0184 (2)
H16A	0.8027	0.6979	0.1070	0.022*
H16B	0.8013	0.6041	0.1322	0.022*
C17	0.69583 (9)	0.68032 (6)	0.18819 (5)	0.0163 (2)
H17A	0.6492	0.7325	0.1789	0.020*
H17B	0.7653	0.6898	0.2272	0.020*
C18	0.60803 (9)	0.61374 (6)	0.21000 (5)	0.0120 (2)
H18	0.6581	0.5619	0.2156	0.014*
C19	0.48660 (9)	0.70312 (6)	0.27985 (5)	0.0147 (2)
H19A	0.4286	0.7079	0.2349	0.018*
H19B	0.5426	0.7516	0.2841	0.018*
C20	0.41211 (9)	0.70173 (6)	0.34134 (5)	0.0145 (2)
C21	0.44026 (9)	0.75553 (6)	0.39824 (5)	0.0171 (2)
H21	0.5065	0.7940	0.3984	0.020*
C22	0.37204 (10)	0.75333 (7)	0.45488 (5)	0.0196 (2)
H22	0.3917	0.7904	0.4933	0.023*
C23	0.27563 (10)	0.69726 (7)	0.45545 (5)	0.0196 (2)
H23	0.2296	0.6956	0.4943	0.024*
C24	0.24625 (10)	0.64323 (7)	0.39889 (6)	0.0197 (2)
H24	0.1801	0.6047	0.3990	0.024*
C25	0.31418 (9)	0.64595 (7)	0.34239 (5)	0.0172 (2)
H25	0.2936	0.6092	0.3038	0.021*
C26	0.66397 (9)	0.63019 (6)	0.33960 (5)	0.0141 (2)
H26A	0.6256	0.6364	0.3834	0.017*
H26B	0.7152	0.6798	0.3350	0.017*
C27	0.75144 (9)	0.55589 (6)	0.34862 (5)	0.0141 (2)
H27A	0.8269	0.5709	0.3820	0.017*
H27B	0.7789	0.5439	0.3024	0.017*
C28	0.69645 (9)	0.47719 (6)	0.37546 (5)	0.0137 (2)
H28	0.6780	0.4864	0.4247	0.016*
C29	0.78903 (9)	0.40598 (7)	0.37584 (5)	0.0182 (2)
H29A	0.7483	0.3551	0.3895	0.022*
H29B	0.8088	0.3982	0.3272	0.022*
C30	0.91137 (10)	0.41840 (8)	0.42597 (6)	0.0260 (3)
H30A	0.9657	0.3706	0.4235	0.039*
H30B	0.8931	0.4248	0.4745	0.039*
H30C	0.9537	0.4678	0.4121	0.039*
C31	0.49519 (9)	0.39720 (6)	0.35440 (5)	0.0128 (2)
H31	0.5424	0.3446	0.3638	0.015*
C32	0.43876 (9)	0.42032 (7)	0.42130 (5)	0.0171 (2)
H32A	0.5070	0.4289	0.4611	0.021*
H32B	0.3916	0.4724	0.4131	0.021*
C33	0.35099 (10)	0.35262 (7)	0.44074 (5)	0.0196 (2)
H33A	0.4000	0.3021	0.4536	0.023*
H33B	0.3128	0.3701	0.4825	0.023*
C34	0.24755 (9)	0.33400 (7)	0.37957 (5)	0.0179 (2)
H34A	0.1921	0.3824	0.3707	0.021*
H34B	0.1965	0.2874	0.3927	0.021*
C35	0.30172 (9)	0.31249 (6)	0.31183 (5)	0.0169 (2)
H35A	0.3502	0.2608	0.3187	0.020*
H35B	0.2329	0.3045	0.2722	0.020*
C36	0.38655 (9)	0.38224 (6)	0.29457 (5)	0.0123 (2)
H36	0.3345	0.4333	0.2903	0.015*
H1	0.4755 (12)	0.4183 (6)	0.2191 (7)	0.030 (4)*
H2	0.5374 (12)	0.5033 (6)	0.3183 (7)	0.029 (4)*
H4	0.4029 (12)	0.5486 (8)	0.2162 (5)	0.023 (3)*

	U11	U22	U33	U12	U13	U23
O1	0.0302 (4)	0.0194 (4)	0.0498 (5)	−0.0036 (3)	0.0049 (4)	0.0009 (4)
O2	0.0298 (5)	0.0338 (5)	0.0338 (5)	0.0102 (4)	0.0020 (4)	0.0097 (4)
O3	0.0268 (4)	0.0291 (4)	0.0266 (4)	−0.0065 (3)	0.0007 (3)	−0.0020 (3)
N1	0.0122 (4)	0.0118 (4)	0.0116 (4)	0.0002 (3)	0.0018 (3)	−0.0005 (3)
N2	0.0117 (4)	0.0136 (4)	0.0129 (4)	−0.0015 (3)	0.0001 (3)	0.0025 (3)
N3	0.0116 (4)	0.0130 (4)	0.0110 (4)	0.0007 (3)	0.0010 (3)	−0.0007 (3)
N4	0.0119 (4)	0.0143 (4)	0.0099 (4)	−0.0016 (3)	0.0010 (3)	0.0004 (3)
N5	0.0194 (4)	0.0223 (5)	0.0225 (4)	0.0007 (3)	0.0078 (3)	0.0010 (3)
C1	0.0175 (5)	0.0145 (5)	0.0156 (5)	0.0049 (4)	0.0037 (4)	0.0013 (4)
C2	0.0135 (4)	0.0169 (5)	0.0140 (4)	0.0048 (4)	0.0014 (3)	0.0009 (4)
C3	0.0174 (5)	0.0174 (5)	0.0176 (5)	0.0029 (4)	0.0013 (4)	−0.0021 (4)
C4	0.0170 (5)	0.0209 (5)	0.0249 (5)	0.0017 (4)	0.0054 (4)	0.0034 (4)
C5	0.0194 (5)	0.0294 (6)	0.0158 (5)	0.0079 (4)	0.0059 (4)	0.0038 (4)
C6	0.0179 (5)	0.0285 (6)	0.0142 (5)	0.0060 (4)	−0.0006 (4)	−0.0040 (4)
C7	0.0132 (4)	0.0206 (5)	0.0180 (5)	0.0031 (4)	0.0005 (4)	−0.0026 (4)
C8	0.0137 (4)	0.0142 (5)	0.0127 (4)	−0.0004 (4)	−0.0004 (3)	−0.0015 (3)
C9	0.0118 (4)	0.0142 (5)	0.0142 (4)	−0.0002 (3)	0.0003 (3)	0.0001 (3)
C10	0.0122 (4)	0.0149 (5)	0.0109 (4)	−0.0008 (4)	−0.0003 (3)	0.0004 (3)
C11	0.0149 (5)	0.0163 (5)	0.0193 (5)	0.0017 (4)	0.0005 (4)	0.0029 (4)
C12	0.0156 (5)	0.0270 (6)	0.0316 (6)	0.0006 (4)	−0.0037 (4)	0.0086 (5)
C13	0.0125 (4)	0.0125 (5)	0.0124 (4)	−0.0008 (3)	0.0017 (3)	0.0013 (3)
C14	0.0171 (5)	0.0196 (5)	0.0122 (4)	−0.0008 (4)	0.0034 (4)	−0.0003 (4)
C15	0.0193 (5)	0.0249 (6)	0.0145 (5)	−0.0019 (4)	0.0059 (4)	0.0031 (4)
C16	0.0154 (5)	0.0223 (5)	0.0186 (5)	−0.0024 (4)	0.0064 (4)	0.0015 (4)
C17	0.0149 (5)	0.0173 (5)	0.0172 (5)	−0.0039 (4)	0.0044 (4)	−0.0002 (4)
C18	0.0113 (4)	0.0133 (5)	0.0116 (4)	−0.0002 (3)	0.0024 (3)	0.0002 (3)
C19	0.0156 (4)	0.0136 (5)	0.0150 (5)	0.0020 (4)	0.0030 (4)	0.0006 (3)
C20	0.0138 (4)	0.0158 (5)	0.0138 (4)	0.0041 (4)	0.0012 (3)	0.0006 (4)
C21	0.0133 (4)	0.0195 (5)	0.0178 (5)	0.0018 (4)	0.0001 (4)	−0.0022 (4)
C22	0.0189 (5)	0.0253 (6)	0.0134 (5)	0.0056 (4)	−0.0014 (4)	−0.0043 (4)
C23	0.0194 (5)	0.0258 (6)	0.0145 (5)	0.0067 (4)	0.0052 (4)	0.0035 (4)
C24	0.0181 (5)	0.0194 (5)	0.0223 (5)	0.0015 (4)	0.0057 (4)	0.0021 (4)
C25	0.0171 (5)	0.0176 (5)	0.0172 (5)	0.0014 (4)	0.0028 (4)	−0.0020 (4)
C26	0.0134 (4)	0.0147 (5)	0.0135 (4)	−0.0012 (4)	−0.0004 (4)	−0.0011 (3)
C27	0.0115 (4)	0.0159 (5)	0.0145 (4)	−0.0012 (4)	−0.0001 (3)	0.0009 (4)
C28	0.0125 (4)	0.0167 (5)	0.0111 (4)	−0.0004 (4)	−0.0004 (3)	0.0006 (3)
C29	0.0163 (5)	0.0186 (5)	0.0191 (5)	0.0024 (4)	0.0004 (4)	0.0033 (4)
C30	0.0157 (5)	0.0284 (6)	0.0322 (6)	0.0014 (4)	−0.0028 (4)	0.0095 (5)
C31	0.0130 (4)	0.0134 (5)	0.0120 (4)	−0.0008 (3)	0.0018 (3)	0.0009 (3)
C32	0.0187 (5)	0.0204 (5)	0.0125 (4)	−0.0027 (4)	0.0036 (4)	−0.0008 (4)
C33	0.0206 (5)	0.0249 (5)	0.0141 (5)	−0.0022 (4)	0.0056 (4)	0.0031 (4)
C34	0.0165 (5)	0.0203 (5)	0.0182 (5)	−0.0025 (4)	0.0069 (4)	0.0022 (4)
C35	0.0171 (5)	0.0173 (5)	0.0168 (5)	−0.0052 (4)	0.0046 (4)	−0.0011 (4)
C36	0.0124 (4)	0.0138 (5)	0.0112 (4)	−0.0004 (3)	0.0030 (3)	0.0001 (3)

O1—N5	1.2557 (13)	C15—H15B	0.9900
O2—N5	1.2470 (13)	C16—C17	1.5297 (13)
O3—N5	1.2536 (12)	C16—H16A	0.9900
N1—C1	1.5063 (12)	C16—H16B	0.9900
N1—C8	1.5107 (12)	C17—C18	1.5357 (13)
N1—C36	1.5189 (11)	C17—H17A	0.9900
N1—H1	0.896 (9)	C17—H17B	0.9900
N2—C31	1.4634 (12)	C18—H18	1.0000
N2—C28	1.4737 (12)	C19—C20	1.5152 (13)
N2—H2	0.877 (9)	C19—H19A	0.9900
N3—C19	1.4734 (12)	C19—H19B	0.9900
N3—C26	1.4840 (12)	C20—C21	1.3947 (14)
N3—C18	1.4842 (11)	C20—C25	1.3954 (14)
N4—C13	1.4753 (12)	C21—C22	1.3933 (14)
N4—C10	1.4793 (11)	C21—H21	0.9500
N4—H4	0.881 (8)	C22—C23	1.3850 (16)
C1—C2	1.5077 (13)	C22—H22	0.9500
C1—H1A	0.9900	C23—C24	1.3937 (15)
C1—H1B	0.9900	C23—H23	0.9500
C2—C3	1.3935 (14)	C24—C25	1.3892 (14)
C2—C7	1.3943 (14)	C24—H24	0.9500
C3—C4	1.3890 (14)	C25—H25	0.9500
C3—H3A	0.9500	C26—C27	1.5286 (13)
C4—C5	1.3940 (16)	C26—H26A	0.9900
C4—H4A	0.9500	C26—H26B	0.9900
C5—C6	1.3844 (16)	C27—C28	1.5308 (13)
C5—H5	0.9500	C27—H27A	0.9900
C6—C7	1.3898 (14)	C27—H27B	0.9900
C6—H6	0.9500	C28—C29	1.5295 (14)
C7—H7	0.9500	C28—H28	1.0000
C8—C9	1.5204 (13)	C29—C30	1.5287 (14)
C8—H8A	0.9900	C29—H29A	0.9900
C8—H8B	0.9900	C29—H29B	0.9900
C9—C10	1.5331 (13)	C30—H30A	0.9800
C9—H9A	0.9900	C30—H30B	0.9800
C9—H9B	0.9900	C30—H30C	0.9800
C10—C11	1.5312 (13)	C31—C36	1.5344 (12)
C10—H10	1.0000	C31—C32	1.5387 (13)
C11—C12	1.5277 (14)	C31—H31	1.0000
C11—H11A	0.9900	C32—C33	1.5328 (14)
C11—H11B	0.9900	C32—H32A	0.9900
C12—H12A	0.9800	C32—H32B	0.9900
C12—H12B	0.9800	C33—C34	1.5256 (14)
C12—H12C	0.9800	C33—H33A	0.9900
C13—C14	1.5326 (13)	C33—H33B	0.9900
C13—C18	1.5378 (12)	C34—C35	1.5344 (13)
C13—H13	1.0000	C34—H34A	0.9900
C14—C15	1.5336 (14)	C34—H34B	0.9900
C14—H14A	0.9900	C35—C36	1.5238 (13)
C14—H14B	0.9900	C35—H35A	0.9900
C15—C16	1.5245 (14)	C35—H35B	0.9900
C15—H15A	0.9900	C36—H36	1.0000
C1—N1—C8	110.14 (7)	C16—C17—H17B	109.6
C1—N1—C36	113.44 (7)	C18—C17—H17B	109.6
C8—N1—C36	114.00 (7)	H17A—C17—H17B	108.1
C1—N1—H1	109.2 (9)	N3—C18—C17	115.38 (8)
C8—N1—H1	106.1 (9)	N3—C18—C13	111.61 (7)
C36—N1—H1	103.4 (9)	C17—C18—C13	110.41 (8)
C31—N2—C28	117.74 (7)	N3—C18—H18	106.3
C31—N2—H2	109.3 (9)	C17—C18—H18	106.3
C28—N2—H2	108.9 (9)	C13—C18—H18	106.3
C19—N3—C26	108.30 (7)	N3—C19—C20	110.80 (8)
C19—N3—C18	113.43 (7)	N3—C19—H19A	109.5
C26—N3—C18	113.09 (7)	C20—C19—H19A	109.5
C13—N4—C10	117.05 (7)	N3—C19—H19B	109.5
C13—N4—H4	106.9 (9)	C20—C19—H19B	109.5
C10—N4—H4	108.9 (9)	H19A—C19—H19B	108.1
O2—N5—O3	120.46 (10)	C21—C20—C25	118.57 (9)
O2—N5—O1	119.90 (9)	C21—C20—C19	120.93 (9)
O3—N5—O1	119.64 (9)	C25—C20—C19	120.51 (9)
N1—C1—C2	110.71 (8)	C22—C21—C20	120.56 (10)
N1—C1—H1A	109.5	C22—C21—H21	119.7
C2—C1—H1A	109.5	C20—C21—H21	119.7
N1—C1—H1B	109.5	C23—C22—C21	120.26 (9)
C2—C1—H1B	109.5	C23—C22—H22	119.9
H1A—C1—H1B	108.1	C21—C22—H22	119.9
C3—C2—C7	119.47 (9)	C22—C23—C24	119.83 (9)
C3—C2—C1	120.00 (9)	C22—C23—H23	120.1
C7—C2—C1	120.53 (9)	C24—C23—H23	120.1
C4—C3—C2	120.45 (9)	C25—C24—C23	119.68 (10)
C4—C3—H3A	119.8	C25—C24—H24	120.2
C2—C3—H3A	119.8	C23—C24—H24	120.2
C3—C4—C5	119.63 (10)	C24—C25—C20	121.11 (9)
C3—C4—H4A	120.2	C24—C25—H25	119.4
C5—C4—H4A	120.2	C20—C25—H25	119.4
C6—C5—C4	120.20 (9)	N3—C26—C27	116.35 (8)
C6—C5—H5	119.9	N3—C26—H26A	108.2
C4—C5—H5	119.9	C27—C26—H26A	108.2
C5—C6—C7	120.15 (10)	N3—C26—H26B	108.2
C5—C6—H6	119.9	C27—C26—H26B	108.2
C7—C6—H6	119.9	H26A—C26—H26B	107.4
C6—C7—C2	120.10 (10)	C26—C27—C28	115.93 (8)
C6—C7—H7	120.0	C26—C27—H27A	108.3
C2—C7—H7	120.0	C28—C27—H27A	108.3
N1—C8—C9	114.58 (8)	C26—C27—H27B	108.3
N1—C8—H8A	108.6	C28—C27—H27B	108.3
C9—C8—H8A	108.6	H27A—C27—H27B	107.4
N1—C8—H8B	108.6	N2—C28—C29	110.17 (8)
C9—C8—H8B	108.6	N2—C28—C27	108.73 (7)
H8A—C8—H8B	107.6	C29—C28—C27	110.59 (8)
C8—C9—C10	114.44 (8)	N2—C28—H28	109.1
C8—C9—H9A	108.7	C29—C28—H28	109.1
C10—C9—H9A	108.7	C27—C28—H28	109.1
C8—C9—H9B	108.7	C30—C29—C28	114.03 (9)
C10—C9—H9B	108.7	C30—C29—H29A	108.7
H9A—C9—H9B	107.6	C28—C29—H29A	108.7
N4—C10—C11	113.13 (8)	C30—C29—H29B	108.7
N4—C10—C9	108.99 (7)	C28—C29—H29B	108.7
C11—C10—C9	110.91 (8)	H29A—C29—H29B	107.6
N4—C10—H10	107.9	C29—C30—H30A	109.5
C11—C10—H10	107.9	C29—C30—H30B	109.5
C9—C10—H10	107.9	H30A—C30—H30B	109.5
C12—C11—C10	114.31 (9)	C29—C30—H30C	109.5
C12—C11—H11A	108.7	H30A—C30—H30C	109.5
C10—C11—H11A	108.7	H30B—C30—H30C	109.5
C12—C11—H11B	108.7	N2—C31—C36	107.60 (7)
C10—C11—H11B	108.7	N2—C31—C32	116.47 (8)
H11A—C11—H11B	107.6	C36—C31—C32	107.83 (8)
C11—C12—H12A	109.5	N2—C31—H31	108.2
C11—C12—H12B	109.5	C36—C31—H31	108.2
H12A—C12—H12B	109.5	C32—C31—H31	108.2
C11—C12—H12C	109.5	C33—C32—C31	110.91 (8)
H12A—C12—H12C	109.5	C33—C32—H32A	109.5
H12B—C12—H12C	109.5	C31—C32—H32A	109.5
N4—C13—C14	111.39 (8)	C33—C32—H32B	109.5
N4—C13—C18	107.91 (7)	C31—C32—H32B	109.5
C14—C13—C18	109.56 (8)	H32A—C32—H32B	108.0
N4—C13—H13	109.3	C34—C33—C32	111.53 (8)
C14—C13—H13	109.3	C34—C33—H33A	109.3
C18—C13—H13	109.3	C32—C33—H33A	109.3
C13—C14—C15	111.35 (8)	C34—C33—H33B	109.3
C13—C14—H14A	109.4	C32—C33—H33B	109.3
C15—C14—H14A	109.4	H33A—C33—H33B	108.0
C13—C14—H14B	109.4	C33—C34—C35	111.45 (8)
C15—C14—H14B	109.4	C33—C34—H34A	109.3
H14A—C14—H14B	108.0	C35—C34—H34A	109.3
C16—C15—C14	111.55 (8)	C33—C34—H34B	109.3
C16—C15—H15A	109.3	C35—C34—H34B	109.3
C14—C15—H15A	109.3	H34A—C34—H34B	108.0
C16—C15—H15B	109.3	C36—C35—C34	109.00 (8)
C14—C15—H15B	109.3	C36—C35—H35A	109.9
H15A—C15—H15B	108.0	C34—C35—H35A	109.9
C15—C16—C17	110.92 (8)	C36—C35—H35B	109.9
C15—C16—H16A	109.5	C34—C35—H35B	109.9
C17—C16—H16A	109.5	H35A—C35—H35B	108.3
C15—C16—H16B	109.5	N1—C36—C35	113.28 (8)
C17—C16—H16B	109.5	N1—C36—C31	110.70 (7)
H16A—C16—H16B	108.0	C35—C36—C31	112.06 (8)
C16—C17—C18	110.15 (8)	N1—C36—H36	106.8
C16—C17—H17A	109.6	C35—C36—H36	106.8
C18—C17—H17A	109.6	C31—C36—H36	106.8
C8—N1—C1—C2	66.13 (10)	C26—N3—C19—C20	−70.03 (9)
C36—N1—C1—C2	−164.73 (8)	C18—N3—C19—C20	163.57 (8)
N1—C1—C2—C3	74.22 (11)	N3—C19—C20—C21	111.49 (10)
N1—C1—C2—C7	−105.98 (10)	N3—C19—C20—C25	−68.03 (11)
C7—C2—C3—C4	0.50 (15)	C25—C20—C21—C22	0.13 (15)
C1—C2—C3—C4	−179.69 (9)	C19—C20—C21—C22	−179.40 (9)
C2—C3—C4—C5	−0.15 (15)	C20—C21—C22—C23	0.30 (15)
C3—C4—C5—C6	−0.24 (16)	C21—C22—C23—C24	−0.43 (15)
C4—C5—C6—C7	0.29 (16)	C22—C23—C24—C25	0.12 (15)
C5—C6—C7—C2	0.05 (15)	C23—C24—C25—C20	0.32 (15)
C3—C2—C7—C6	−0.45 (15)	C21—C20—C25—C24	−0.44 (15)
C1—C2—C7—C6	179.74 (9)	C19—C20—C25—C24	179.09 (9)
C1—N1—C8—C9	−175.10 (8)	C19—N3—C26—C27	178.66 (8)
C36—N1—C8—C9	56.07 (10)	C18—N3—C26—C27	−54.73 (11)
N1—C8—C9—C10	71.93 (10)	N3—C26—C27—C28	−73.19 (10)
C13—N4—C10—C11	−68.49 (10)	C31—N2—C28—C29	73.32 (10)
C13—N4—C10—C9	167.63 (8)	C31—N2—C28—C27	−165.34 (8)
C8—C9—C10—N4	−50.59 (10)	C26—C27—C28—N2	53.90 (10)
C8—C9—C10—C11	−175.77 (8)	C26—C27—C28—C29	174.98 (8)
N4—C10—C11—C12	177.23 (8)	N2—C28—C29—C30	−176.58 (8)
C9—C10—C11—C12	−59.95 (11)	C27—C28—C29—C30	63.19 (11)
C10—N4—C13—C14	−67.86 (10)	C28—N2—C31—C36	−175.09 (8)
C10—N4—C13—C18	171.85 (7)	C28—N2—C31—C32	63.80 (11)
N4—C13—C14—C15	−175.82 (8)	N2—C31—C32—C33	178.67 (8)
C18—C13—C14—C15	−56.50 (10)	C36—C31—C32—C33	57.68 (10)
C13—C14—C15—C16	55.23 (11)	C31—C32—C33—C34	−56.30 (11)
C14—C15—C16—C17	−55.12 (12)	C32—C33—C34—C35	54.94 (12)
C15—C16—C17—C18	56.98 (11)	C33—C34—C35—C36	−55.57 (11)
C19—N3—C18—C17	61.89 (10)	C1—N1—C36—C35	−67.88 (10)
C26—N3—C18—C17	−61.94 (10)	C8—N1—C36—C35	59.27 (10)
C19—N3—C18—C13	−65.20 (10)	C1—N1—C36—C31	58.97 (10)
C26—N3—C18—C13	170.97 (8)	C8—N1—C36—C31	−173.89 (8)
C16—C17—C18—N3	173.18 (8)	C34—C35—C36—N1	−174.29 (8)
C16—C17—C18—C13	−59.12 (10)	C34—C35—C36—C31	59.58 (10)
N4—C13—C18—N3	−50.19 (10)	N2—C31—C36—N1	45.54 (10)
C14—C13—C18—N3	−171.62 (8)	C32—C31—C36—N1	171.92 (8)
N4—C13—C18—C17	−179.93 (7)	N2—C31—C36—C35	173.06 (7)
C14—C13—C18—C17	58.63 (10)	C32—C31—C36—C35	−60.55 (10)

Cg1 and Cg2 are the centroids of the C2–C7 and C20–C25 benzene rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···N2	0.90 (1)	2.32 (1)	2.7400 (11)	108.(1)
N1—H1···N4	0.90 (1)	2.12 (1)	2.8156 (11)	134.(1)
N2—H2···N3	0.88 (1)	2.19 (1)	2.9293 (11)	142.(1)
N4—H4···N3	0.88 (1)	2.33 (1)	2.7992 (11)	113.(1)
C1—H1a···O1	0.99	2.36	3.2096 (13)	143
C9—H9a···O3i	0.99	2.40	3.3620 (12)	165
C34—H34a···O3i	0.99	2.50	3.3876 (13)	150
C8—H8a···Cg3ii	0.99	2.53	3.4008 (11)	146
C26—H26b···Cg1iii	0.99	2.71	3.5899 (11)	149

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 and Cg2 are the centroids of the C2–C7 and C20–C25 benzene rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯N2	0.90 (1)	2.32 (1)	2.7400 (11)	108 (1)
N1—H1⋯N4	0.90 (1)	2.12 (1)	2.8156 (11)	134 (1)
N2—H2⋯N3	0.88 (1)	2.19 (1)	2.9293 (11)	142 (1)
N4—H4⋯N3	0.88 (1)	2.33 (1)	2.7992 (11)	113 (1)
C1—H1a⋯O1	0.99	2.36	3.2096 (13)	143
C9—H9a⋯O3i	0.99	2.40	3.3620 (12)	165
C34—H34a⋯O3i	0.99	2.50	3.3876 (13)	150
C8—H8a⋯Cg3ii	0.99	2.53	3.4008 (11)	146
C26—H26b⋯Cg1iii	0.99	2.71	3.5899 (11)	149

Symmetry codes: (i) ; (ii) ; (iii) .