N-Methyl-N-(2-pyridinio­methyl)-2-[N-(2-pyridinio­methyl)­methyl­amino]-N-(2-pyridyl­methyl)­ethanaminium tris(perchlorate)

The crystal structure of the title compound, C₂₂H₃₀N₅³⁺·3ClO₄⁻, at 180 K contains intramolecular N—H...N and intermolec­ular N—H...O hydrogen bonds.

Key indicators

• Single-crystal X-ray study
• T = 180 K
• Mean [sigma](C-C) = 0.004 Å
• R factor = 0.056
• wR factor = 0.154
• Data-to-parameter ratio = 14.9

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ ....          ?
PLAT244_ALERT_4_C Low  Solvent U(eq) as Compared to Neighbors  for        Cl1
PLAT244_ALERT_4_C Low  Solvent U(eq) as Compared to Neighbors  for        Cl2
PLAT244_ALERT_4_C Low  Solvent U(eq) as Compared to Neighbors  for        Cl3

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   4 ALERT level C = Check and explain
   0 ALERT level G = General alerts; check

   1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   0 ALERT type 2 Indicator that the structure model may be wrong or deficient
   0 ALERT type 3 Indicator that the structure quality may be low
   3 ALERT type 4 Improvement, methodology, query or suggestion

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Computing details

Data collection: APEX2 (Bruker-Nonius, 2004); cell refinement: SAINT (Bruker, 2003); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2000); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

N-Methyl-N-(2-pyridiniomethyl)-2-[N-(3-pyridiniomethyl)methylamino]- N-(2-pyridylmethyl)ethanaminium triperchlorate

Crystal data

C22H30N5^3+·3ClO4^−	F(000) = 1376
Mr = 662.86	Dx = 1.586 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 8693 reflections
a = 13.6004 (3) Å	θ = 2.8–26.4°
b = 8.7668 (2) Å	µ = 0.40 mm^−1
c = 23.5440 (5) Å	T = 180 K
β = 98.493 (1)°	Block, colourless
V = 2776.41 (11) Å^3	0.25 × 0.20 × 0.20 mm
Z = 4

Data collection

Bruker–Nonius X8APEX-II CCD diffractometer	5653 independent reflections
Radiation source: fine-focus sealed tube	4549 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.033
thin–slice ω and φ scans	θmax = 26.4°, θmin = 3.7°
Absorption correction: multi-scan (SADABS; Sheldrick, 2003)	h = −16→16
Tmin = 0.841, Tmax = 0.924	k = −10→10
55950 measured reflections	l = −29→29

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.056	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.154	H-atom parameters constrained
S = 1.06	w = 1/[σ^2(Fo^2) + (0.0667P)^2 + 5.5837P] where P = (Fo^2 + 2Fc^2)/3
5653 reflections	(Δ/σ)max < 0.001
379 parameters	Δρmax = 1.25 e Å^−3
0 restraints	Δρmin = −1.10 e Å^−3

Special details

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.

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
N1	−0.1568 (2)	0.5060 (4)	0.40930 (12)	0.0405 (7)
H1B	−0.2034	0.4378	0.3987	0.049*
N2	−0.09675 (18)	0.5762 (3)	0.26788 (10)	0.0277 (5)
N3	0.08714 (17)	0.4901 (3)	0.19285 (10)	0.0223 (5)
N4	0.10675 (18)	0.3549 (3)	0.06489 (10)	0.0258 (5)
H4B	0.1691	0.3730	0.0792	0.031*
N5	0.27891 (19)	0.4493 (3)	0.12877 (11)	0.0285 (5)
C1	−0.1483 (3)	0.5618 (5)	0.46301 (15)	0.0480 (9)
H1A	−0.1919	0.5275	0.4884	0.058*
C2	−0.0775 (3)	0.6667 (4)	0.48084 (14)	0.0404 (8)
H2A	−0.0703	0.7067	0.5187	0.048*
C3	−0.0163 (3)	0.7141 (4)	0.44285 (16)	0.0470 (9)
H3A	0.0337	0.7882	0.4544	0.056*
C4	−0.0268 (3)	0.6548 (4)	0.38802 (14)	0.0388 (8)
H4A	0.0158	0.6880	0.3620	0.047*
C5	−0.0986 (2)	0.5484 (3)	0.37116 (12)	0.0262 (6)
C6	−0.1155 (2)	0.4717 (4)	0.31340 (13)	0.0308 (7)
H6A	−0.0709	0.3823	0.3139	0.037*
H6B	−0.1850	0.4347	0.3054	0.037*
C7	−0.1749 (3)	0.6936 (4)	0.25923 (15)	0.0434 (9)
H7A	−0.1765	0.7487	0.2953	0.065*
H7B	−0.2394	0.6449	0.2471	0.065*
H7C	−0.1607	0.7653	0.2296	0.065*
C8	−0.0948 (2)	0.4941 (4)	0.21349 (12)	0.0287 (6)
H8A	−0.1030	0.5689	0.1816	0.034*
H8B	−0.1521	0.4234	0.2072	0.034*
C9	0.0001 (2)	0.4037 (3)	0.21137 (12)	0.0255 (6)
H9A	−0.0161	0.3168	0.1848	0.031*
H9B	0.0221	0.3606	0.2500	0.031*
C10	0.1129 (2)	0.6250 (3)	0.23135 (12)	0.0256 (6)
H10A	0.1689	0.6800	0.2191	0.038*
H10B	0.1313	0.5900	0.2710	0.038*
H10C	0.0553	0.6931	0.2290	0.038*
C11	0.0640 (2)	0.5506 (3)	0.13169 (12)	0.0236 (6)
H11A	0.0095	0.6261	0.1302	0.028*
H11B	0.1234	0.6050	0.1223	0.028*
C12	0.0344 (2)	0.4319 (3)	0.08627 (12)	0.0244 (6)
C13	−0.0630 (2)	0.4057 (4)	0.06372 (13)	0.0306 (6)
H13A	−0.1148	0.4593	0.0781	0.037*
C14	−0.0853 (2)	0.3004 (4)	0.01979 (13)	0.0340 (7)
H14A	−0.1526	0.2816	0.0039	0.041*
C15	−0.0098 (2)	0.2228 (4)	−0.00087 (13)	0.0327 (7)
H15A	−0.0244	0.1502	−0.0309	0.039*
C16	0.0871 (2)	0.2521 (3)	0.02264 (13)	0.0307 (7)
H16A	0.1399	0.1995	0.0089	0.037*
C17	0.1744 (2)	0.3779 (3)	0.19977 (12)	0.0250 (6)
H17A	0.1861	0.3419	0.2401	0.030*
H17B	0.1556	0.2882	0.1750	0.030*
C18	0.2704 (2)	0.4420 (3)	0.18502 (12)	0.0255 (6)
C19	0.3476 (2)	0.4836 (3)	0.22752 (13)	0.0273 (6)
H19A	0.3396	0.4796	0.2669	0.033*
C20	0.4369 (2)	0.5311 (4)	0.21128 (14)	0.0332 (7)
H20A	0.4918	0.5562	0.2396	0.040*
C21	0.4449 (2)	0.5414 (4)	0.15400 (15)	0.0361 (7)
H21A	0.5048	0.5757	0.1420	0.043*
C22	0.3638 (2)	0.5008 (4)	0.11388 (14)	0.0333 (7)
H22A	0.3690	0.5101	0.0742	0.040*
Cl1	0.27605 (5)	0.93272 (9)	0.11899 (3)	0.02912 (19)
O1	0.2646 (2)	1.0886 (3)	0.13408 (15)	0.0639 (8)
O2	0.2358 (3)	0.8386 (4)	0.15794 (14)	0.0790 (11)
O3	0.2237 (3)	0.9072 (5)	0.06382 (13)	0.1008 (14)
O4	0.3778 (2)	0.9008 (4)	0.1204 (2)	0.0920 (13)
Cl2	0.92833 (5)	1.00293 (8)	0.13467 (3)	0.02686 (18)
O5	0.87627 (19)	0.9867 (3)	0.07743 (10)	0.0437 (6)
O6	1.01730 (17)	1.0894 (3)	0.13370 (11)	0.0426 (6)
O7	0.86590 (18)	1.0787 (3)	0.16942 (11)	0.0500 (7)
O8	0.9552 (2)	0.8565 (3)	0.15862 (12)	0.0556 (7)
Cl3	0.68573 (6)	0.59405 (11)	0.07137 (4)	0.0438 (2)
O9	0.7506 (4)	0.7019 (4)	0.1032 (2)	0.138 (2)
O10	0.7030 (3)	0.4562 (5)	0.1014 (2)	0.1117 (17)
O11	0.5874 (3)	0.6371 (8)	0.0625 (2)	0.157 (3)
O12	0.7180 (3)	0.5883 (9)	0.01942 (17)	0.146 (3)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N1	0.0336 (15)	0.0618 (19)	0.0269 (14)	−0.0169 (13)	0.0067 (11)	−0.0003 (13)
N2	0.0308 (13)	0.0303 (13)	0.0233 (12)	0.0064 (10)	0.0082 (10)	0.0025 (10)
N3	0.0286 (12)	0.0185 (11)	0.0201 (11)	0.0008 (9)	0.0046 (9)	−0.0001 (9)
N4	0.0291 (12)	0.0262 (12)	0.0219 (12)	0.0014 (10)	0.0036 (9)	−0.0003 (10)
N5	0.0327 (13)	0.0267 (13)	0.0269 (13)	0.0054 (10)	0.0073 (10)	−0.0010 (10)
C1	0.0414 (19)	0.078 (3)	0.0264 (17)	−0.0109 (19)	0.0104 (14)	0.0017 (18)
C2	0.048 (2)	0.048 (2)	0.0260 (16)	0.0022 (16)	0.0076 (14)	−0.0035 (14)
C3	0.064 (2)	0.040 (2)	0.0384 (19)	−0.0179 (18)	0.0127 (17)	−0.0080 (16)
C4	0.051 (2)	0.0356 (17)	0.0342 (17)	−0.0110 (15)	0.0189 (15)	−0.0041 (14)
C5	0.0249 (14)	0.0282 (15)	0.0261 (15)	0.0050 (11)	0.0060 (11)	0.0034 (12)
C6	0.0337 (16)	0.0309 (16)	0.0288 (16)	−0.0026 (13)	0.0077 (13)	−0.0011 (12)
C7	0.0458 (19)	0.051 (2)	0.0360 (18)	0.0212 (17)	0.0153 (15)	0.0098 (16)
C8	0.0263 (14)	0.0357 (16)	0.0239 (15)	−0.0011 (12)	0.0034 (11)	0.0002 (12)
C9	0.0304 (15)	0.0234 (14)	0.0230 (14)	−0.0015 (11)	0.0054 (11)	0.0004 (11)
C10	0.0332 (15)	0.0199 (13)	0.0237 (14)	−0.0006 (11)	0.0047 (12)	−0.0029 (11)
C11	0.0300 (14)	0.0204 (13)	0.0209 (14)	0.0034 (11)	0.0049 (11)	0.0016 (11)
C12	0.0301 (14)	0.0225 (14)	0.0210 (13)	0.0041 (11)	0.0047 (11)	0.0012 (11)
C13	0.0316 (15)	0.0331 (16)	0.0266 (15)	0.0048 (13)	0.0033 (12)	0.0002 (12)
C14	0.0359 (17)	0.0357 (17)	0.0284 (16)	−0.0022 (13)	−0.0024 (13)	0.0033 (13)
C15	0.0476 (19)	0.0276 (15)	0.0221 (14)	−0.0040 (14)	0.0031 (13)	−0.0025 (12)
C16	0.0418 (17)	0.0273 (15)	0.0241 (15)	0.0031 (13)	0.0083 (13)	−0.0014 (12)
C17	0.0289 (14)	0.0209 (13)	0.0254 (14)	0.0038 (11)	0.0049 (11)	0.0042 (11)
C18	0.0305 (15)	0.0196 (13)	0.0271 (15)	0.0043 (11)	0.0067 (12)	0.0028 (11)
C19	0.0308 (15)	0.0227 (14)	0.0278 (15)	0.0031 (11)	0.0029 (12)	0.0018 (12)
C20	0.0311 (16)	0.0294 (16)	0.0383 (18)	0.0008 (12)	0.0027 (13)	−0.0009 (13)
C21	0.0319 (16)	0.0349 (17)	0.0443 (19)	0.0000 (13)	0.0145 (14)	0.0014 (15)
C22	0.0374 (17)	0.0354 (17)	0.0300 (16)	0.0046 (13)	0.0145 (13)	0.0020 (13)
Cl1	0.0329 (4)	0.0335 (4)	0.0213 (3)	−0.0079 (3)	0.0053 (3)	−0.0043 (3)
O1	0.0657 (19)	0.0350 (15)	0.085 (2)	0.0060 (13)	−0.0083 (16)	−0.0076 (14)
O2	0.120 (3)	0.064 (2)	0.065 (2)	−0.012 (2)	0.054 (2)	0.0141 (17)
O3	0.120 (3)	0.145 (4)	0.0338 (17)	−0.041 (3)	−0.0007 (18)	−0.029 (2)
O4	0.0403 (17)	0.060 (2)	0.178 (4)	0.0012 (15)	0.023 (2)	−0.007 (2)
Cl2	0.0311 (4)	0.0238 (3)	0.0261 (4)	0.0055 (3)	0.0057 (3)	0.0010 (3)
O5	0.0488 (14)	0.0523 (15)	0.0284 (12)	0.0000 (12)	0.0000 (10)	−0.0043 (11)
O6	0.0351 (12)	0.0473 (15)	0.0454 (14)	−0.0048 (11)	0.0064 (10)	0.0044 (11)
O7	0.0390 (13)	0.0662 (18)	0.0471 (15)	0.0113 (12)	0.0144 (11)	−0.0155 (13)
O8	0.0717 (19)	0.0303 (13)	0.0613 (17)	0.0094 (13)	−0.0013 (14)	0.0138 (12)
Cl3	0.0344 (4)	0.0558 (5)	0.0418 (5)	0.0060 (4)	0.0081 (3)	0.0042 (4)
O9	0.211 (5)	0.056 (2)	0.113 (3)	0.028 (3)	−0.084 (4)	−0.020 (2)
O10	0.079 (3)	0.075 (2)	0.164 (4)	−0.023 (2)	−0.041 (3)	0.061 (3)
O11	0.049 (2)	0.287 (7)	0.146 (4)	0.074 (3)	0.050 (2)	0.156 (5)
O12	0.076 (3)	0.312 (8)	0.052 (2)	0.033 (4)	0.0221 (19)	0.000 (3)

Geometric parameters (Å, º)

N1—C5	1.335 (4)	C10—H10C	0.980
N1—C1	1.345 (4)	C11—C12	1.504 (4)
N1—H1B	0.880	C11—H11A	0.990
N2—C6	1.461 (4)	C11—H11B	0.990
N2—C7	1.472 (4)	C12—C13	1.372 (4)
N2—C8	1.472 (4)	C13—C14	1.386 (4)
N3—C10	1.500 (3)	C13—H13A	0.950
N3—C9	1.522 (4)	C14—C15	1.380 (5)
N3—C11	1.523 (3)	C14—H14A	0.9500
N3—C17	1.532 (3)	C15—C16	1.375 (4)
N4—C16	1.340 (4)	C15—H15A	0.950
N4—C12	1.350 (4)	C16—H16A	0.950
N4—H4B	0.880	C17—C18	1.507 (4)
N5—C22	1.334 (4)	C17—H17A	0.990
N5—C18	1.348 (4)	C17—H17B	0.990
C1—C2	1.353 (5)	C18—C19	1.388 (4)
C1—H1A	0.950	C19—C20	1.390 (4)
C2—C3	1.373 (5)	C19—H19A	0.950
C2—H2A	0.950	C20—C21	1.372 (5)
C3—C4	1.379 (5)	C20—H20A	0.950
C3—H3A	0.950	C21—C22	1.388 (5)
C4—C5	1.366 (4)	C21—H21A	0.950
C4—H4A	0.950	C22—H22A	0.950
C5—C6	1.504 (4)	Cl1—O3	1.404 (3)
C6—H6A	0.990	Cl1—O2	1.404 (3)
C6—H6B	0.990	Cl1—O4	1.407 (3)
C7—H7A	0.980	Cl1—O1	1.427 (3)
C7—H7B	0.980	Cl2—O7	1.427 (2)
C7—H7C	0.980	Cl2—O8	1.428 (3)
C8—C9	1.522 (4)	Cl2—O6	1.431 (2)
C8—H8A	0.990	Cl2—O5	1.434 (2)
C8—H8B	0.990	Cl3—O12	1.360 (4)
C9—H9A	0.990	Cl3—O11	1.375 (3)
C9—H9B	0.990	Cl3—O10	1.403 (4)
C10—H10A	0.980	Cl3—O9	1.428 (4)
C10—H10B	0.980
C5—N1—C1	123.7 (3)	C12—C11—N3	115.3 (2)
C5—N1—H1B	118.2	C12—C11—H11A	108.5
C1—N1—H1B	118.2	N3—C11—H11A	108.5
C6—N2—C7	109.8 (2)	C12—C11—H11B	108.5
C6—N2—C8	111.1 (2)	N3—C11—H11B	108.5
C7—N2—C8	109.1 (2)	H11A—C11—H11B	107.5
C10—N3—C9	110.0 (2)	N4—C12—C13	119.2 (3)
C10—N3—C11	107.1 (2)	N4—C12—C11	118.5 (3)
C9—N3—C11	112.5 (2)	C13—C12—C11	122.2 (3)
C10—N3—C17	109.5 (2)	C12—C13—C14	119.5 (3)
C9—N3—C17	105.9 (2)	C12—C13—H13A	120.2
C11—N3—C17	111.9 (2)	C14—C13—H13A	120.2
C16—N4—C12	122.4 (3)	C15—C14—C13	119.9 (3)
C16—N4—H4B	118.8	C15—C14—H14A	120.0
C12—N4—H4B	118.8	C13—C14—H14A	120.0
C22—N5—C18	118.5 (3)	C16—C15—C14	119.0 (3)
N1—C1—C2	119.8 (3)	C16—C15—H15A	120.5
N1—C1—H1A	120.1	C14—C15—H15A	120.5
C2—C1—H1A	120.1	N4—C16—C15	119.9 (3)
C1—C2—C3	118.4 (3)	N4—C16—H16A	120.0
C1—C2—H2A	120.8	C15—C16—H16A	120.0
C3—C2—H2A	120.8	C18—C17—N3	114.8 (2)
C2—C3—C4	120.4 (3)	C18—C17—H17A	108.6
C2—C3—H3A	119.8	N3—C17—H17A	108.6
C4—C3—H3A	119.8	C18—C17—H17B	108.6
C5—C4—C3	120.0 (3)	N3—C17—H17B	108.6
C5—C4—H4A	120.0	H17A—C17—H17B	107.5
C3—C4—H4A	120.0	N5—C18—C19	122.0 (3)
N1—C5—C4	117.7 (3)	N5—C18—C17	116.6 (3)
N1—C5—C6	117.2 (3)	C19—C18—C17	121.4 (3)
C4—C5—C6	125.1 (3)	C18—C19—C20	118.6 (3)
N2—C6—C5	111.3 (2)	C18—C19—H19A	120.7
N2—C6—H6A	109.4	C20—C19—H19A	120.7
C5—C6—H6A	109.4	C21—C20—C19	119.3 (3)
N2—C6—H6B	109.4	C21—C20—H20A	120.3
C5—C6—H6B	109.4	C19—C20—H20A	120.3
H6A—C6—H6B	108.0	C20—C21—C22	118.8 (3)
N2—C7—H7A	109.5	C20—C21—H21A	120.6
N2—C7—H7B	109.5	C22—C21—H21A	120.6
H7A—C7—H7B	109.5	N5—C22—C21	122.6 (3)
N2—C7—H7C	109.5	N5—C22—H22A	118.7
H7A—C7—H7C	109.5	C21—C22—H22A	118.7
H7B—C7—H7C	109.5	O3—Cl1—O2	108.5 (2)
N2—C8—C9	114.0 (2)	O3—Cl1—O4	110.6 (3)
N2—C8—H8A	108.7	O2—Cl1—O4	110.2 (2)
C9—C8—H8A	108.7	O3—Cl1—O1	108.9 (2)
N2—C8—H8B	108.7	O2—Cl1—O1	109.5 (2)
C9—C8—H8B	108.7	O4—Cl1—O1	109.2 (2)
H8A—C8—H8B	107.6	O7—Cl2—O8	109.36 (18)
C8—C9—N3	116.7 (2)	O7—Cl2—O6	109.78 (16)
C8—C9—H9A	108.1	O8—Cl2—O6	108.38 (16)
N3—C9—H9A	108.1	O7—Cl2—O5	109.38 (15)
C8—C9—H9B	108.1	O8—Cl2—O5	110.12 (16)
N3—C9—H9B	108.1	O6—Cl2—O5	109.80 (15)
H9A—C9—H9B	107.3	O12—Cl3—O11	108.0 (3)
N3—C10—H10A	109.5	O12—Cl3—O10	111.6 (4)
N3—C10—H10B	109.5	O11—Cl3—O10	113.6 (3)
H10A—C10—H10B	109.5	O12—Cl3—O9	103.9 (4)
N3—C10—H10C	109.5	O11—Cl3—O9	114.1 (4)
H10A—C10—H10C	109.5	O10—Cl3—O9	105.1 (2)
H10B—C10—H10C	109.5
C5—N1—C1—C2	−0.1 (6)	C16—N4—C12—C11	−177.1 (3)
N1—C1—C2—C3	0.4 (6)	N3—C11—C12—N4	−83.8 (3)
C1—C2—C3—C4	−0.4 (6)	N3—C11—C12—C13	100.0 (3)
C2—C3—C4—C5	0.1 (6)	N4—C12—C13—C14	0.4 (4)
C1—N1—C5—C4	−0.3 (5)	C11—C12—C13—C14	176.6 (3)
C1—N1—C5—C6	178.1 (3)	C12—C13—C14—C15	0.0 (5)
C3—C4—C5—N1	0.2 (5)	C13—C14—C15—C16	−0.2 (5)
C3—C4—C5—C6	−178.0 (3)	C12—N4—C16—C15	0.6 (4)
C7—N2—C6—C5	−70.0 (3)	C14—C15—C16—N4	−0.1 (5)
C8—N2—C6—C5	169.3 (2)	C10—N3—C17—C18	−60.0 (3)
N1—C5—C6—N2	146.1 (3)	C9—N3—C17—C18	−178.5 (2)
C4—C5—C6—N2	−35.7 (4)	C11—N3—C17—C18	58.6 (3)
C6—N2—C8—C9	−75.8 (3)	C22—N5—C18—C19	−1.3 (4)
C7—N2—C8—C9	163.0 (3)	C22—N5—C18—C17	−177.9 (3)
N2—C8—C9—N3	−85.6 (3)	N3—C17—C18—N5	−79.7 (3)
C10—N3—C9—C8	56.7 (3)	N3—C17—C18—C19	103.6 (3)
C11—N3—C9—C8	−62.5 (3)	N5—C18—C19—C20	−1.3 (4)
C17—N3—C9—C8	174.9 (2)	C17—C18—C19—C20	175.2 (3)
C10—N3—C11—C12	−179.0 (2)	C18—C19—C20—C21	2.6 (4)
C9—N3—C11—C12	−58.0 (3)	C19—C20—C21—C22	−1.3 (5)
C17—N3—C11—C12	61.0 (3)	C18—N5—C22—C21	2.6 (5)
C16—N4—C12—C13	−0.7 (4)	C20—C21—C22—N5	−1.3 (5)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1B···O5^i	0.88	2.53	3.051 (4)	118
N1—H1B···O9^i	0.88	2.16	2.951 (5)	149
N4—H4B···N5	0.88	1.88	2.718 (4)	159

Symmetry code: (i) −x+1/2, y−1/2, −z+1/2.