N,N′-Di­cyclo­hexyl-N-(2-pyrazinoyl)­urea

The title compound, C₁₈H₂₆N₄O₂, is obtainable from 1,3-di­cyclo­hexyl­carbodi­imide and pyrazine-2-carboxyl­ic acid in di­methyl­form­amide in the presence of catalytic amounts of [H₃Ru₄(C₆H₆)₄OH]Cl₂. The intermolecular N—H...O=C hydrogen bond is responsible for the formation of infinite chains stretching along the a axis of the crystal.

Key indicators

• Single-crystal X-ray study
• T = 153 K
• Mean [sigma](C-C) = 0.002 Å
• R factor = 0.028
• wR factor = 0.058
• Data-to-parameter ratio = 10.8

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry


 Alert Level C:



ABSMU_01  Alert C The ratio of given/expected absorption coefficient lies
          outside the range 0.99 <> 1.01
          Calculated value of mu =     0.082
          Value of mu given      =     0.080

STRVAL_01
         From the CIF: _refine_ls_abs_structure_Flack    0.800
         From the CIF: _refine_ls_abs_structure_Flack_su    0.900
           Alert C Chirality of atom sites is inverted?

General Notes



REFLT_03
         From the CIF: _diffrn_reflns_theta_max           26.00
         From the CIF: _reflns_number_total               3477
         Count of symmetry unique reflns         2016
         Completeness (_total/calc)            172.47%
         TEST3: Check Friedels for noncentro structure
         Estimate of Friedel pairs measured      1461
         Fraction of Friedel pairs measured     0.725
         Are heavy atom types Z>Si present           no
          ALERT: MoKa measured Friedel data cannot be used to
                 determine absolute structure in a light-atom
                 study EXCEPT under VERY special conditions.
                 It is preferred that Friedel data is merged in such cases.


 0 Alert Level A = Potentially serious problem

 0 Alert Level B = Potential problem

 2 Alert Level C = Please check

---

S1. Comment

N,N'-Dicyclohexyl-N-(2-pyrazinoyl)urea, (I), is formed quantitatively from 1,3-dicyclohexylcarbodiimide and pyrazine-2-carboxylic acid in dimethylformamide at room temperature, if small amounts of [H₃Ru₄(C₆H₆)₄OH]Cl₂ are present as catalyst; (I) crystallizes directly from the reaction solution. In the absence of the catalyst, (I) seems to be formed as well, although much more slowly; no crystallization occurs under these conditions. The catalyst, [H₃Ru₄(C₆H₆)₄OH]Cl₂, is readily available according to the published methods (Chérioux et al., 2001). The precise role of the catalyst in this reaction is not well established, but it can be recovered unchanged after the reaction. Only in the presence of the catalyst, the reaction, being complete after 2 h, gives (I) as an air-stable colorless block-shaped crystalline product.

Compound (I) is analogous to N,N'-dicyclohexyl-N-nicotinoylurea, (II), which has been synthesized in a complex reaction from L-phenylalanine-L-leucine ethyl ester, nicotinic acid, 1-hydroxybenzotriazole and 1,3-dicyclohexylcarbodiimide in dichloromethane (Gallagher et al., 1999).

In the molecular structure of (I) (Fig. 1), the average values of the C—C—C bond angles in the two cyclohexane rings (111.0 and 111.2°) and the absolute values of torsion angles (average 55.9 and 55.5°), agree with the theoretically predicted values of 111.5 and 54.7° for a chair conformation (Bixon & Lifson, 1967). The bond lengths and angles are in accordance with those in related structures (Orpen et al., 1994).

Intermolecular hydrogen bonding involving the N4 amide H atom and carbonyl atom O2 leads to the formation of infinite chains running parallel to the a axis of the crystal (Fig. 2). Similar intermolecular (amide)N—H···O═C hydrogen bonding leading to the formation of infinite chains is observed in the structure of N,N'-dicyclohexylurea, (III) (Govindasamy & Subramanian, 1997). The H···O distance of N—H···O═C in (I) [2.929 (2) Å] is slightly shorter than that in (III) [2.962 (5) Å], which may be due to the fact that carbonyl O atom in (III), in contrast to that in (I), participates in two hydrogen bonds involving both `active' H atoms of the next molecule in the chain. In the structure of (II), however, with two independent molecules, there are three symmetry independent hydrogen bonds of two different kinds, namely [(amide)N—H···N(py) and (py)C—H···O═ C(amide)], which leads to the formation of a totally different, much more complex, hydrogen-bonded system.

S2. Experimental

N,N'-Dicyclohexyl-N-(2-pyrazinoyl)urea is formed quantitatively when pyrazine-2-carboxylic acid (1.0 g, 8 mmol), 1,3-dicyclohexylcarbodiimide (2.1 g, 10 mmol) and [H₃Ru₄(C₆H₆)₄OH]Cl₂ (7 mg, 0.008 mmol) are dissolved under N₂ in dimethylformamide (20 ml). The red solution is stirred for 2 h at 293 K and filtered. The product crystallizes at room temperature from the filtrate. Crystals were collected by filtration. ¹H NMR (200 MHz, CDCl₃): 1.22 (m, 10H), 1.55 (m, 10H), 3.55(quint-d, 1H), 4.23 (quint, 1H), 5.94 (d, 1H), 8.51 (dd, 1H), 8.66 (d, 1H), 8.98 (d, 1H); IR (KBr, cm^-1): 3278 (NH, sharp), 1703 (CO, amide) and 1681 (CO, urea); MS (ESI, m/z): 330.

S3. Refinement

Image plate experiment parameters: image plate distance 70 mm; ϕ oscillation scans: 0–200°; step: Δϕ = 1.5°; 2θ range: 3.27–52.1°; d_max-d_min = 12.45–0.81 Å. The H atoms were located from Fourier difference maps and refined isotropically [N4—H4N 0.91 (2) Å and C—H 0.95–1.04 Å]. The absolute structure could not be determined because of the lack of anomalous scatterers.

Computing details

Data collection: EXPOSE (Stoe & Cie, 2000); cell refinement: CELL (Stoe & Cie, 2000); data reduction: INTEGRATE (Stoe & Cie, 2000); program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON99 (Spek, 1990); software used to prepare material for publication: SHELXL97.

Figures

	Fig. 1. The molecular structure of (I) showing the atom-numbering scheme. Displacement ellipsoids are drawn at the 40% probability level. H atoms have been omitted for clarity.
	Fig. 2. Packing diagram of (I) showing the intermolecular hydrogen bonds in the crystal.

N,N'-dicyclohexyl-N-(2-pyrazinoyl)urea

Crystal data

C18H26N4O2	Dx = 1.229 Mg m^−3
Mr = 330.43	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, P212121	Cell parameters from 8000 reflections
a = 9.4745 (8) Å	θ = 2.5–26.0°
b = 11.9101 (7) Å	µ = 0.08 mm^−1
c = 15.8212 (10) Å	T = 153 K
V = 1785.3 (2) Å^3	Block, colourless
Z = 4	0.50 × 0.40 × 0.35 mm
F(000) = 712

Data collection

Stoe IPDS diffractometer	2753 reflections with I > 2σ(I'
Radiation source: fine-focus sealed tube	Rint = 0.039
Graphite monochromator	θmax = 26.0°, θmin = 2.5°
Detector resolution: 0.81Å pixels mm^-1	h = −11→11
ϕ oscillation scans	k = −14→14
14006 measured reflections	l = −19→19
3477 independent reflections

Refinement

Refinement on F^2	Hydrogen site location: difference Fourier map
Least-squares matrix: full	All H-atom parameters refined
R[F^2 > 2σ(F^2)] = 0.028	w = 1/[σ^2(Fo^2) + (0.0337P)^2] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.058	(Δ/σ)max < 0.001
S = 0.90	Δρmax = 0.13 e Å^−3
3477 reflections	Δρmin = −0.13 e Å^−3
322 parameters	Extinction correction: SHELXL97, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
0 restraints	Extinction coefficient: 0.0134 (14)
Primary atom site location: structure-invariant direct methods	Absolute structure: Flack (1983)
Secondary atom site location: difference Fourier map	Absolute structure parameter: 0.8 (9)

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	−0.12365 (15)	1.04710 (11)	0.64837 (8)	0.0440 (3)
N2	0.07686 (13)	0.87429 (11)	0.66026 (8)	0.0360 (3)
N3	−0.04493 (11)	0.67152 (9)	0.57379 (7)	0.0256 (3)
N4	−0.05157 (13)	0.79709 (10)	0.46233 (7)	0.0287 (3)
H4N	−0.1446 (18)	0.7980 (13)	0.4751 (9)	0.037 (4)*
O1	−0.17785 (10)	0.69206 (8)	0.69294 (6)	0.0323 (2)
O2	0.15069 (9)	0.70008 (8)	0.48796 (6)	0.0314 (2)
C1	0.10916 (18)	0.98278 (15)	0.67237 (10)	0.0410 (4)
H1	0.2078 (17)	1.0009 (14)	0.6858 (10)	0.045 (5)*
C2	0.0114 (2)	1.06673 (15)	0.66609 (9)	0.0425 (4)
H2	0.0373 (18)	1.1429 (16)	0.6745 (11)	0.051 (5)*
C3	−0.15860 (16)	0.93919 (13)	0.63910 (9)	0.0346 (3)
H3	−0.2577 (16)	0.9185 (12)	0.6257 (10)	0.033 (4)*
C4	−0.05965 (15)	0.85401 (11)	0.64453 (8)	0.0278 (3)
C5	−0.10154 (13)	0.73230 (11)	0.63833 (9)	0.0257 (3)
C6	−0.06060 (15)	0.54705 (11)	0.57213 (9)	0.0292 (3)
H6	−0.1376 (17)	0.5309 (14)	0.6117 (11)	0.044 (4)*
C7	0.07149 (17)	0.48790 (13)	0.60310 (11)	0.0359 (3)
H7A	0.1494 (16)	0.5102 (14)	0.5660 (10)	0.040 (4)*
H7B	0.0951 (16)	0.5152 (14)	0.6615 (10)	0.041 (4)*
C8	0.0495 (2)	0.36082 (13)	0.60406 (11)	0.0426 (4)
H8A	−0.0241 (17)	0.3432 (13)	0.6449 (10)	0.038 (4)*
H8B	0.1398 (19)	0.3237 (15)	0.6248 (12)	0.058 (5)*
C9	0.0048 (2)	0.31828 (14)	0.51738 (11)	0.0455 (4)
H9A	−0.013 (2)	0.2379 (19)	0.5176 (13)	0.072 (6)*
H9B	0.0844 (19)	0.3341 (14)	0.4790 (12)	0.050 (5)*
C10	−0.12585 (19)	0.37844 (13)	0.48638 (11)	0.0420 (4)
H10A	−0.1516 (17)	0.3531 (14)	0.4297 (11)	0.044 (4)*
H10B	−0.2078 (18)	0.3610 (13)	0.5228 (11)	0.043 (4)*
C11	−0.10444 (17)	0.50623 (12)	0.48511 (10)	0.0351 (3)
H11A	−0.1969 (19)	0.5475 (14)	0.4677 (11)	0.052 (5)*
H11B	−0.0254 (18)	0.5278 (14)	0.4461 (10)	0.044 (4)*
C12	0.02807 (13)	0.72465 (10)	0.50482 (8)	0.0251 (3)
C13	0.00045 (16)	0.86535 (12)	0.39215 (9)	0.0308 (3)
H13	0.0960 (17)	0.8426 (13)	0.3830 (10)	0.038 (4)*
C14	−0.08914 (17)	0.84509 (13)	0.31398 (10)	0.0333 (3)
H14A	−0.1858 (17)	0.8643 (13)	0.3271 (10)	0.037 (4)*
H14B	−0.0879 (16)	0.7617 (14)	0.3000 (11)	0.043 (4)*
C15	−0.03838 (19)	0.91729 (13)	0.24048 (10)	0.0395 (4)
H15A	0.0616 (18)	0.8943 (14)	0.2252 (10)	0.045 (4)*
H15B	−0.0989 (16)	0.9050 (13)	0.1933 (11)	0.039 (4)*
C16	−0.0367 (2)	1.04086 (13)	0.26391 (10)	0.0424 (4)
H16A	0.0027 (15)	1.0880 (14)	0.2137 (10)	0.040 (4)*
H16B	−0.131 (2)	1.0662 (15)	0.2765 (11)	0.052 (5)*
C17	0.0525 (2)	1.06203 (15)	0.34241 (10)	0.0430 (4)
H17A	0.1518 (19)	1.0441 (14)	0.3286 (10)	0.043 (5)*
H17B	0.0534 (19)	1.1449 (17)	0.3580 (11)	0.056 (5)*
C18	0.00298 (18)	0.98971 (14)	0.41614 (10)	0.0363 (4)
H18A	−0.0946 (17)	1.0082 (14)	0.4343 (10)	0.038 (4)*
H18B	0.0625 (17)	1.0025 (14)	0.4662 (10)	0.044 (4)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N1	0.0591 (9)	0.0307 (7)	0.0421 (8)	0.0022 (6)	−0.0050 (7)	−0.0075 (6)
N2	0.0334 (7)	0.0382 (8)	0.0363 (7)	−0.0085 (6)	−0.0022 (5)	−0.0031 (6)
N3	0.0278 (6)	0.0226 (6)	0.0265 (6)	−0.0006 (5)	0.0027 (5)	0.0020 (5)
N4	0.0233 (6)	0.0324 (6)	0.0305 (6)	0.0029 (5)	0.0041 (5)	0.0083 (5)
O1	0.0352 (5)	0.0345 (5)	0.0273 (5)	−0.0040 (4)	0.0044 (5)	0.0032 (5)
O2	0.0238 (5)	0.0355 (5)	0.0349 (5)	0.0017 (4)	0.0037 (4)	0.0039 (5)
C1	0.0440 (10)	0.0436 (10)	0.0355 (9)	−0.0160 (8)	−0.0015 (7)	−0.0042 (7)
C2	0.0634 (12)	0.0336 (9)	0.0305 (8)	−0.0121 (8)	−0.0016 (8)	−0.0035 (7)
C3	0.0374 (8)	0.0312 (8)	0.0351 (8)	0.0014 (7)	0.0004 (7)	−0.0050 (7)
C4	0.0312 (7)	0.0295 (7)	0.0226 (7)	−0.0026 (6)	0.0016 (6)	0.0005 (6)
C5	0.0244 (6)	0.0290 (7)	0.0238 (7)	0.0012 (6)	−0.0023 (6)	0.0022 (6)
C6	0.0308 (7)	0.0256 (8)	0.0313 (7)	−0.0030 (6)	0.0024 (7)	0.0009 (6)
C7	0.0416 (9)	0.0284 (8)	0.0377 (8)	0.0015 (7)	−0.0051 (7)	0.0021 (7)
C8	0.0556 (10)	0.0275 (8)	0.0449 (9)	0.0055 (8)	−0.0032 (9)	0.0028 (7)
C9	0.0625 (11)	0.0282 (9)	0.0458 (10)	0.0010 (8)	0.0052 (9)	−0.0042 (8)
C10	0.0536 (10)	0.0354 (9)	0.0369 (9)	−0.0090 (7)	0.0000 (8)	−0.0050 (8)
C11	0.0388 (8)	0.0304 (8)	0.0361 (8)	−0.0025 (7)	−0.0052 (7)	0.0000 (7)
C12	0.0251 (7)	0.0240 (7)	0.0261 (7)	−0.0028 (5)	0.0011 (6)	−0.0009 (6)
C13	0.0263 (7)	0.0348 (8)	0.0312 (7)	0.0031 (6)	0.0049 (6)	0.0089 (7)
C14	0.0428 (9)	0.0271 (8)	0.0299 (8)	0.0037 (7)	0.0022 (7)	−0.0003 (6)
C15	0.0489 (10)	0.0419 (10)	0.0276 (8)	0.0030 (8)	0.0017 (8)	0.0043 (7)
C16	0.0540 (11)	0.0391 (9)	0.0342 (8)	−0.0055 (8)	−0.0039 (8)	0.0110 (7)
C17	0.0488 (10)	0.0395 (10)	0.0408 (9)	−0.0117 (9)	−0.0060 (8)	0.0091 (8)
C18	0.0366 (8)	0.0401 (9)	0.0320 (8)	−0.0080 (7)	−0.0043 (7)	0.0030 (7)

Geometric parameters (Å, º)

N1—C2	1.330 (2)	C8—H8B	1.017 (19)
N1—C3	1.335 (2)	C9—C10	1.512 (3)
N2—C4	1.3390 (19)	C9—H9A	0.97 (2)
N2—C1	1.342 (2)	C9—H9B	0.986 (19)
N3—C5	1.3617 (17)	C10—C11	1.536 (2)
N3—C6	1.4902 (17)	C10—H10A	0.977 (17)
N3—C12	1.4386 (16)	C10—H10B	0.989 (18)
N4—C12	1.3287 (17)	C11—H11A	1.041 (18)
N4—C13	1.4618 (18)	C11—H11B	1.004 (17)
N4—H4N	0.905 (17)	C13—C14	1.519 (2)
O1—C5	1.2243 (16)	C13—C18	1.529 (2)
O2—C12	1.2274 (15)	C13—H13	0.956 (17)
C1—C2	1.367 (3)	C14—C15	1.524 (2)
C1—H1	0.983 (16)	C14—H14A	0.966 (16)
C2—H2	0.950 (19)	C14—H14B	1.018 (17)
C3—C4	1.384 (2)	C15—C16	1.518 (2)
C3—H3	0.993 (15)	C15—H15A	1.015 (17)
C4—C5	1.5061 (19)	C15—H15B	0.953 (17)
C6—C7	1.517 (2)	C16—C17	1.523 (2)
C6—C11	1.518 (2)	C16—H16A	1.043 (16)
C6—H6	0.980 (17)	C16—H16B	0.967 (18)
C7—C8	1.528 (2)	C17—C18	1.524 (2)
C7—H7A	0.979 (17)	C17—H17A	0.989 (17)
C7—H7B	1.004 (16)	C17—H17B	1.017 (19)
C8—C9	1.522 (2)	C18—H18A	0.993 (16)
C8—H8A	0.974 (17)	C18—H18B	0.984 (17)
C2—N1—C3	115.51 (14)	C11—C10—H10A	109.1 (10)
C4—N2—C1	114.87 (13)	C9—C10—H10B	110.7 (9)
C5—N3—C12	121.63 (10)	C11—C10—H10B	108.7 (9)
C5—N3—C6	120.19 (11)	H10A—C10—H10B	105.9 (13)
C12—N3—C6	118.17 (11)	C6—C11—C10	109.98 (13)
C12—N4—C13	123.64 (12)	C6—C11—H11A	108.6 (9)
C12—N4—H4N	116.7 (10)	C10—C11—H11A	111.1 (9)
C13—N4—H4N	119.4 (10)	C6—C11—H11B	105.8 (9)
N2—C1—C2	122.66 (16)	C10—C11—H11B	111.1 (10)
N2—C1—H1	117.4 (10)	H11A—C11—H11B	110.1 (13)
C2—C1—H1	120.0 (10)	O2—C12—N4	125.62 (12)
N1—C2—C1	122.59 (16)	O2—C12—N3	121.00 (11)
N1—C2—H2	116.5 (11)	N4—C12—N3	113.35 (11)
C1—C2—H2	120.9 (11)	N4—C13—C14	109.98 (12)
N1—C3—C4	122.06 (14)	N4—C13—C18	110.81 (12)
N1—C3—H3	119.8 (8)	C14—C13—C18	111.39 (12)
C4—C3—H3	118.1 (8)	N4—C13—H13	106.1 (10)
N2—C4—C3	122.25 (13)	C14—C13—H13	111.2 (10)
N2—C4—C5	116.12 (12)	C18—C13—H13	107.3 (9)
C3—C4—C5	121.53 (13)	C13—C14—C15	110.80 (13)
O1—C5—N3	123.62 (12)	C13—C14—H14A	108.4 (9)
O1—C5—C4	119.11 (12)	C15—C14—H14A	109.2 (9)
N3—C5—C4	117.17 (11)	C13—C14—H14B	109.0 (9)
N3—C6—C7	111.96 (11)	C15—C14—H14B	112.4 (9)
N3—C6—C11	111.22 (12)	H14A—C14—H14B	106.8 (13)
C7—C6—C11	111.71 (12)	C16—C15—C14	111.36 (13)
N3—C6—H6	105.0 (10)	C16—C15—H15A	108.0 (9)
C7—C6—H6	108.4 (10)	C14—C15—H15A	108.9 (9)
C11—C6—H6	108.2 (10)	C16—C15—H15B	110.3 (10)
C6—C7—C8	110.53 (13)	C14—C15—H15B	108.7 (10)
C6—C7—H7A	107.6 (9)	H15A—C15—H15B	109.5 (13)
C8—C7—H7A	112.2 (10)	C15—C16—C17	111.44 (14)
C6—C7—H7B	109.3 (9)	C15—C16—H16A	109.9 (9)
C8—C7—H7B	110.0 (9)	C17—C16—H16A	109.5 (8)
H7A—C7—H7A	107.2 (13)	C15—C16—H16B	110.0 (11)
C9—C8—C7	111.02 (14)	C17—C16—H16B	107.2 (10)
C9—C8—H8A	109.1 (9)	H16A—C16—H16B	108.7 (13)
C7—C8—H8A	108.5 (9)	C16—C17—C18	111.09 (13)
C9—C8—H8B	112.3 (10)	C16—C17—H17A	108.2 (9)
C7—C8—H8B	108.6 (10)	C18—C17—H17A	109.9 (9)
H8A—C8—H8B	107.1 (14)	C16—C17—H17B	111.3 (10)
C10—C9—C8	111.24 (14)	C18—C17—H17B	111.4 (10)
C10—C9—H9A	109.0 (12)	H17A—C17—H17B	104.7 (14)
C8—C9—H9A	111.9 (13)	C17—C18—C13	111.24 (13)
C10—C9—H9B	109.6 (10)	C17—C18—H18A	112.5 (9)
C8—C9—H9B	106.1 (10)	C13—C18—H18A	105.8 (9)
H9A—C9—H9B	108.9 (16)	C17—C18—H18B	110.6 (9)
C9—C10—C11	111.45 (14)	C13—C18—H18B	111.0 (10)
C9—C10—H10A	110.8 (10)	H18A—C18—H18B	105.5 (13)
C4—N2—C1—C2	−2.3 (2)	C6—C7—C8—C9	55.8 (2)
C3—N1—C2—C1	1.6 (2)	C7—C8—C9—C10	−55.6 (2)
N2—C1—C2—N1	0.7 (3)	C8—C9—C10—C11	55.8 (2)
C2—N1—C3—C4	−2.3 (2)	N3—C6—C11—C10	−177.59 (12)
C1—N2—C4—C3	1.6 (2)	C7—C6—C11—C10	56.51 (18)
C1—N2—C4—C5	−174.76 (13)	C9—C10—C11—C6	−55.82 (19)
N1—C3—C4—N2	0.7 (2)	C13—N4—C12—O2	−5.0 (2)
N1—C3—C4—C5	176.86 (13)	C13—N4—C12—N3	177.08 (12)
C12—N3—C5—O1	171.40 (12)	C5—N3—C12—O2	122.52 (13)
C6—N3—C5—O1	−7.11 (19)	C6—N3—C12—O2	−58.94 (17)
C12—N3—C5—C4	−12.32 (18)	C5—N3—C12—N4	−59.46 (16)
C6—N3—C5—C4	169.17 (11)	C6—N3—C12—N4	119.08 (13)
N2—C4—C5—O1	112.14 (14)	C12—N4—C13—C14	123.92 (14)
C3—C4—C5—O1	−64.25 (19)	C12—N4—C13—C18	−112.48 (15)
N2—C4—C5—N3	−64.31 (17)	N4—C13—C14—C15	178.88 (12)
C3—C4—C5—N3	119.29 (14)	C18—C13—C14—C15	55.62 (17)
C5—N3—C6—C7	−100.16 (14)	C13—C14—C15—C16	−55.91 (19)
C12—N3—C6—C7	81.28 (15)	C14—C15—C16—C17	55.8 (2)
C5—N3—C6—C11	134.08 (13)	C15—C16—C17—C18	−55.2 (2)
C12—N3—C6—C11	−44.48 (16)	C16—C17—C18—C13	54.8 (2)
N3—C6—C7—C8	177.62 (13)	N4—C13—C18—C17	−178.13 (13)
C11—C6—C7—C8	−56.89 (18)	C14—C13—C18—C17	−55.35 (18)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N4—H4N···O2^i	0.905 (17)	2.025 (17)	2.9287 (15)	176.1 (14)

Symmetry code: (i) x−1/2, −y+3/2, −z+1.