3-tert-Butyl-5-[(4-methoxy­benzyl­idene)­amino]-1-phenyl­pyrazole

Low, J.N.; Cobo, J.; Nogueras, M.; Sánchez, A.; Rengifo, E.; Abonia, R.

doi:10.1107/S1600536803001909

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3-tert-Butyl-5-[(4-methoxybenzylidene)amino]-1-phenylpyrazole

J. N. Low, J. Cobo, M. Nogueras, A. Sánchez, E. Rengifo and R. Abonia

The title compound, C₂₁H₂₃N₃O, has a supramolecular structure which is determined by a very weak C—H

O(methoxy) hydrogen bond and a similarly weak C—H

π interaction.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536803001909/na6198sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536803001909/na6198Isup2.hkl Contains datablock I

CCDC reference: 204722

checkCIF report

Key indicators

Single-crystal X-ray study
T = 120 K
Mean (C-C) = 0.003 Å
R factor = 0.052
wR factor = 0.135
Data-to-parameter ratio = 16.4

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry


 Alert Level C:



REFLT_03
         From the CIF: _diffrn_reflns_theta_max           27.45
         From the CIF: _reflns_number_total               3762
         TEST2: Reflns within _diffrn_reflns_theta_max
         Count of symmetry unique reflns         4088
         Completeness (_total/calc)             92.03%
          Alert C: < 95% complete


 0 Alert Level A = Potentially serious problem

 0 Alert Level B = Potential problem

 1 Alert Level C = Please check

Comment top

The title compound, (I), was prepared as an intermediate in the preparation of new pyrazole fused derivatives (see Scheme below).

There are no unusual bonds or angles (Table 1) in the pyrazole ring, which is planar to within experimental error.

The mean plane of the phenyl ring attached to N2 is tilted at 26.70 (9)° to the mean plane of the pyrazole ring. The torsion angles involving the methoxy carbon, C341, show that the methoxy group is almost but not quite coplanar with the phenyl ring to which it is attached [C33–C34–O34–C341 = 5.1 (2)°], there is a tendency for methoxy groups to be coplanar with the phenyl ring in anisoles [see Domiano et al. (1979)]

The supramolecular structure is determined by two very weak interactions involving phenyl H atoms (Table 2). The C4—H4···O34 bond links the molecules at (x, y, z) and (1 − x, −y, −z) into a a head-to-tail centrosymmetric R²₂(20) dimer (Bernstein et al., 1995), formed about the centre of symmetry at (1/2, 0,0) (Fig. 2). These dimers are then linked by a C—H···π interaction into a ribbon which runs parallel to the b axis, this is formed by the interaction C25—H25···centroid of the phenyl ring attached to N2 (Fig. 3).

Examination of the structure with PLATON (Spek, 2002) showed that there were no solvent-accessible voids in the crystal lattice.

Experimental top

A mixture of 3-amino-5-(tert-butyl)-2-phenyl-2H-pyrazole (0.11 g, 0.512 mmol), p-methoxybenzaldehyde (0.07 g, 0.514 mmol) and ethanol (10 ml) was heated to reflux for 5 min. After cooling, the pale yellow solid which formed was filtered off and washed with ethanol (85% yield; m.p. 394 K). ¹H NMR (300 MHz, CDCl₃, p.p.m.): 1.39 (9H, s), 3.85 (3H, s), 6.20 (1H, s), 6.95 (2H, d, J = 9.0 Hz), 7.26 (1H, t, J = 9.0 Hz), 7.42 (2H, br t), 7.79 (4H, br d), 8.58 (1H, s, N═CH); ¹³C NMR (75 MHz, CDCl₃, p.p.m.): 30.4, 32.5, 55.4, 89.7, 114.3, 124.1, 126.1, 128.4, 129.0, 130.8, 139.9, 150.4, 159.2 (N═CH), 162.1, 162.6; MS (70 eV): m/e (%) 333 (95), 318 (73), 291 (44), 77 (100), 51 (48), 41 (77). Crystals suitable for single-crystal X-ray diffraction were grown from a solution in ethanol.

Computing details top

Data collection: KappaCCD Server Software (Nonius, 1997); cell refinement: DENZO–SMN (Otwinowski & Minor, 1997); data reduction: DENZO–SMN; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPII (Johnson, 1976) and PLATON (Spek, 2002); software used to prepare material for publication: SHELXL97 and WORDPERFECT macro PRPKAPPA (Ferguson, 1999).

Figures top

	Fig. 1. A view of (I) with the atomic numbering scheme. Displacement ellipsoids are drawn at the 30% probability level.
	Fig. 2. A view of the the R²₂(20) centrosymmetric dimer.
	Fig. 3. Stereoview showing the dimers linked by the C—H···π interaction. Methyl H atoms have been omitted for clarity.

3-tert-butyl-5-[(4-methoxybenzylidene)amino]-1-phenylpyrazole top

Crystal data top

C₂₁H₂₃N₃O	F(000) = 712
M_r = 333.42	D_x = 1.237 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
a = 10.0744 (3) Å	Cell parameters from 3762 reflections
b = 6.2583 (2) Å	θ = 3.2–27.5°
c = 28.9244 (9) Å	µ = 0.08 mm⁻¹
β = 101.0410 (13)°	T = 120 K
V = 1789.89 (10) Å³	Block, brown
Z = 4	0.40 × 0.20 × 0.10 mm

Data collection top

Nonius KappaCCD diffractometer	3762 independent reflections
Radiation source: fine-focus sealed X-ray tube	2710 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.056
ϕ scans and ω scans with κ offsets	θ_max = 27.5°, θ_min = 3.2°
Absorption correction: multi-scan (DENZO–SMN; Otwinowski & Minor, 1997)	h = −11→13
T_min = 0.970, T_max = 0.992	k = −8→4
9156 measured reflections	l = −37→31

Refinement top

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)] = 0.052	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.135	H-atom parameters constrained
S = 1.04	w = 1/[σ²(F_o²) + (0.0575P)² + 0.7158P] where P = (F_o² + 2F_c²)/3
3762 reflections	(Δ/σ)_max < 0.001
230 parameters	Δρ_max = 0.46 e Å⁻³
0 restraints	Δρ_min = −0.33 e Å⁻³

Crystal data top

C₂₁H₂₃N₃O	V = 1789.89 (10) Å³
M_r = 333.42	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 10.0744 (3) Å	µ = 0.08 mm⁻¹
b = 6.2583 (2) Å	T = 120 K
c = 28.9244 (9) Å	0.40 × 0.20 × 0.10 mm
β = 101.0410 (13)°

Data collection top

Nonius KappaCCD diffractometer	3762 independent reflections
Absorption correction: multi-scan (DENZO–SMN; Otwinowski & Minor, 1997)	2710 reflections with I > 2σ(I)
T_min = 0.970, T_max = 0.992	R_int = 0.056
9156 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.052	0 restraints
wR(F²) = 0.135	H-atom parameters constrained
S = 1.04	Δρ_max = 0.46 e Å⁻³
3762 reflections	Δρ_min = −0.33 e Å⁻³
230 parameters

Special details top

Experimental. The program DENZO-SMN (Otwinowski & Minor, 1997) uses a scaling algorithm (Fox & Holmes, 1966) which effectively corrects for absorption effects. High redundancy data were used in the scaling program hence the 'multi-scan' code word was used. No transmission coefficients are available from the program (only scale factors for each frame). The scale factors in the experimental table are calculated from the 'size' command in the SHELXL97 input file.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
N1	0.21013 (14)	0.6008 (2)	0.17069 (5)	0.0215 (3)
N2	0.32887 (13)	0.5996 (2)	0.15426 (5)	0.0195 (3)
C21	0.43008 (17)	0.7516 (3)	0.17282 (6)	0.0201 (4)
C22	0.56627 (17)	0.7080 (3)	0.17514 (6)	0.0241 (4)
C23	0.66133 (18)	0.8601 (3)	0.19416 (7)	0.0286 (4)
C24	0.62257 (18)	1.0517 (3)	0.21143 (7)	0.0274 (4)
C25	0.48641 (18)	1.0928 (3)	0.20909 (6)	0.0248 (4)
C26	0.38998 (18)	0.9439 (3)	0.18996 (6)	0.0218 (4)
C3	0.33061 (17)	0.4384 (3)	0.12247 (6)	0.0193 (4)
N3	0.43791 (14)	0.4147 (2)	0.09877 (5)	0.0213 (3)
C37	0.46951 (17)	0.2236 (3)	0.08898 (6)	0.0216 (4)
C31	0.57039 (16)	0.1785 (3)	0.06040 (6)	0.0194 (4)
C32	0.62042 (17)	0.3385 (3)	0.03502 (6)	0.0221 (4)
C33	0.71205 (17)	0.2945 (3)	0.00625 (6)	0.0228 (4)
C34	0.75693 (16)	0.0856 (3)	0.00348 (6)	0.0206 (4)
O34	0.84677 (12)	0.0230 (2)	−0.02368 (4)	0.0255 (3)
C341	0.90609 (19)	0.1862 (3)	−0.04779 (7)	0.0307 (5)
C35	0.70938 (17)	−0.0763 (3)	0.02908 (6)	0.0227 (4)
C36	0.61608 (17)	−0.0306 (3)	0.05694 (6)	0.0223 (4)
C4	0.20824 (17)	0.3353 (3)	0.11775 (6)	0.0224 (4)
C5	0.13743 (17)	0.4415 (3)	0.14827 (6)	0.0216 (4)
C51	−0.00362 (18)	0.4000 (3)	0.15686 (7)	0.0265 (4)
C52	−0.0148 (2)	0.4669 (4)	0.20646 (8)	0.0433 (6)
C53	−0.1036 (2)	0.5377 (4)	0.12246 (8)	0.0459 (6)
C54	−0.0413 (3)	0.1673 (4)	0.14818 (14)	0.0711 (10)
H22	0.5940	0.5759	0.1639	0.029*
H23	0.7546	0.8323	0.1953	0.034*
H24	0.6887	1.1539	0.2247	0.033*
H25	0.4590	1.2244	0.2207	0.030*
H26	0.2967	0.9728	0.1885	0.026*
H37	0.4254	0.1073	0.1008	0.026*
H32	0.5909	0.4815	0.0375	0.027*
H33	0.7438	0.4052	−0.0113	0.027*
H34A	0.8357	0.2541	−0.0713	0.046*
H34B	0.9745	0.1226	−0.0635	0.046*
H34C	0.9487	0.2936	−0.0251	0.046*
H35	0.7412	−0.2184	0.0274	0.027*
H36	0.5827	−0.1421	0.0739	0.027*
H4	0.1779	0.2169	0.0980	0.027*
H52A	0.0473	0.3810	0.2294	0.065*
H52B	−0.1077	0.4446	0.2110	0.065*
H52C	0.0088	0.6184	0.2110	0.065*
H53A	−0.0808	0.6890	0.1279	0.069*
H53B	−0.1957	0.5122	0.1276	0.069*
H53C	−0.0981	0.4996	0.0900	0.069*
H54A	−0.0384	0.1306	0.1154	0.107*
H54B	−0.1327	0.1433	0.1540	0.107*
H54C	0.0230	0.0775	0.1694	0.107*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N1	0.0182 (7)	0.0242 (8)	0.0231 (8)	−0.0008 (6)	0.0068 (6)	0.0003 (6)
N2	0.0180 (7)	0.0210 (8)	0.0203 (8)	−0.0005 (6)	0.0053 (6)	−0.0015 (6)
C21	0.0218 (9)	0.0217 (9)	0.0164 (8)	−0.0039 (7)	0.0028 (6)	0.0019 (7)
C22	0.0229 (9)	0.0263 (10)	0.0234 (10)	−0.0006 (7)	0.0056 (7)	−0.0033 (8)
C23	0.0205 (9)	0.0364 (11)	0.0287 (10)	−0.0040 (8)	0.0040 (7)	−0.0025 (9)
C24	0.0289 (10)	0.0307 (11)	0.0225 (10)	−0.0103 (8)	0.0045 (8)	−0.0033 (8)
C25	0.0326 (10)	0.0218 (9)	0.0199 (9)	−0.0017 (8)	0.0046 (7)	0.0001 (7)
C26	0.0228 (9)	0.0234 (10)	0.0191 (9)	0.0017 (7)	0.0034 (7)	0.0020 (7)
C3	0.0217 (9)	0.0191 (9)	0.0170 (9)	0.0015 (7)	0.0035 (7)	0.0003 (7)
N3	0.0204 (7)	0.0239 (8)	0.0194 (8)	0.0007 (6)	0.0029 (6)	−0.0021 (6)
C37	0.0215 (9)	0.0230 (9)	0.0194 (9)	−0.0016 (7)	0.0012 (7)	−0.0008 (7)
C31	0.0194 (8)	0.0220 (9)	0.0161 (8)	−0.0008 (7)	0.0014 (7)	−0.0025 (7)
C32	0.0238 (9)	0.0182 (9)	0.0241 (10)	0.0008 (7)	0.0039 (7)	−0.0017 (7)
C33	0.0237 (9)	0.0224 (9)	0.0221 (9)	−0.0032 (7)	0.0040 (7)	0.0014 (7)
C34	0.0190 (8)	0.0243 (9)	0.0182 (9)	−0.0009 (7)	0.0028 (7)	−0.0026 (7)
O34	0.0283 (7)	0.0251 (7)	0.0264 (7)	0.0021 (5)	0.0130 (5)	−0.0005 (6)
C341	0.0328 (10)	0.0335 (11)	0.0291 (11)	0.0023 (8)	0.0143 (8)	0.0052 (9)
C35	0.0250 (9)	0.0183 (9)	0.0247 (10)	0.0017 (7)	0.0042 (7)	−0.0020 (7)
C36	0.0245 (9)	0.0205 (9)	0.0213 (9)	−0.0014 (7)	0.0026 (7)	0.0014 (7)
C4	0.0231 (9)	0.0202 (9)	0.0239 (10)	−0.0013 (7)	0.0044 (7)	−0.0014 (7)
C5	0.0205 (9)	0.0213 (9)	0.0229 (9)	−0.0003 (7)	0.0036 (7)	0.0026 (7)
C51	0.0226 (9)	0.0272 (10)	0.0316 (11)	−0.0041 (8)	0.0101 (8)	−0.0020 (8)
C52	0.0272 (11)	0.0749 (17)	0.0300 (12)	−0.0071 (11)	0.0107 (9)	−0.0017 (11)
C53	0.0223 (10)	0.0754 (18)	0.0394 (13)	−0.0031 (10)	0.0044 (9)	0.0060 (12)
C54	0.0517 (16)	0.0371 (14)	0.140 (3)	−0.0178 (12)	0.0583 (18)	−0.0176 (16)

Geometric parameters (Å, º) top

N1—C5	1.330 (2)	C33—H33	0.9500
N1—N2	1.369 (2)	C34—O34	1.365 (2)
N2—C3	1.367 (2)	C34—C35	1.393 (2)
N2—C21	1.422 (2)	O34—C341	1.430 (2)
C21—C22	1.388 (2)	C341—H34A	0.9800
C21—C26	1.391 (2)	C341—H34B	0.9800
C22—C23	1.387 (2)	C341—H34C	0.9800
C22—H22	0.9500	C35—C36	1.380 (3)
C23—C24	1.384 (3)	C35—H35	0.9500
C23—H23	0.9500	C36—H36	0.9500
C24—C25	1.385 (3)	C4—C5	1.404 (2)
C24—H24	0.9500	C4—H4	0.9500
C25—C26	1.383 (2)	C5—C51	1.511 (2)
C25—H25	0.9500	C51—C54	1.513 (3)
C26—H26	0.9500	C51—C52	1.519 (3)
C3—C4	1.375 (2)	C51—C53	1.537 (3)
C3—N3	1.394 (2)	C52—H52A	0.9800
N3—C37	1.283 (2)	C52—H52B	0.9800
C37—C31	1.455 (2)	C52—H52C	0.9800
C37—H37	0.9500	C53—H53A	0.9800
C31—C32	1.392 (2)	C53—H53B	0.9800
C31—C36	1.397 (2)	C53—H53C	0.9800
C32—C33	1.384 (3)	C54—H54A	0.9800
C32—H32	0.9500	C54—H54B	0.9800
C33—C34	1.391 (2)	C54—H54C	0.9800

C5—N1—N2	105.23 (14)	O34—C341—H34A	109.5
C3—N2—N1	111.23 (13)	O34—C341—H34B	109.5
C3—N2—C21	130.29 (14)	H34A—C341—H34B	109.5
N1—N2—C21	118.43 (14)	O34—C341—H34C	109.5
C22—C21—C26	120.33 (16)	H34A—C341—H34C	109.5
C22—C21—N2	121.16 (15)	H34B—C341—H34C	109.5
C26—C21—N2	118.49 (15)	C36—C35—C34	120.10 (16)
C23—C22—C21	119.03 (17)	C36—C35—H35	119.9
C23—C22—H22	120.5	C34—C35—H35	119.9
C21—C22—H22	120.5	C35—C36—C31	120.44 (17)
C24—C23—C22	121.11 (17)	C35—C36—H36	119.8
C24—C23—H23	119.4	C31—C36—H36	119.8
C22—C23—H23	119.4	C3—C4—C5	105.61 (16)
C23—C24—C25	119.28 (17)	C3—C4—H4	127.2
C23—C24—H24	120.4	C5—C4—H4	127.2
C25—C24—H24	120.4	N1—C5—C4	111.28 (15)
C26—C25—C24	120.49 (17)	N1—C5—C51	119.74 (16)
C26—C25—H25	119.8	C4—C5—C51	128.96 (16)
C24—C25—H25	119.8	C5—C51—C54	110.61 (16)
C25—C26—C21	119.74 (16)	C5—C51—C52	110.49 (15)
C25—C26—H26	120.1	C54—C51—C52	111.1 (2)
C21—C26—H26	120.1	C5—C51—C53	108.49 (16)
N2—C3—C4	106.64 (15)	C54—C51—C53	108.6 (2)
N2—C3—N3	121.34 (15)	C52—C51—C53	107.38 (17)
C4—C3—N3	131.76 (16)	C51—C52—H52A	109.5
C37—N3—C3	117.14 (15)	C51—C52—H52B	109.5
N3—C37—C31	122.41 (16)	H52A—C52—H52B	109.5
N3—C37—H37	118.8	C51—C52—H52C	109.5
C31—C37—H37	118.8	H52A—C52—H52C	109.5
C32—C31—C36	118.58 (16)	H52B—C52—H52C	109.5
C32—C31—C37	121.52 (16)	C51—C53—H53A	109.5
C36—C31—C37	119.87 (16)	C51—C53—H53B	109.5
C33—C32—C31	121.65 (16)	H53A—C53—H53B	109.5
C33—C32—H32	119.2	C51—C53—H53C	109.5
C31—C32—H32	119.2	H53A—C53—H53C	109.5
C32—C33—C34	118.92 (16)	H53B—C53—H53C	109.5
C32—C33—H33	120.5	C51—C54—H54A	109.5
C34—C33—H33	120.5	C51—C54—H54B	109.5
O34—C34—C33	124.19 (16)	H54A—C54—H54B	109.5
O34—C34—C35	115.52 (15)	C51—C54—H54C	109.5
C33—C34—C35	120.29 (16)	H54A—C54—H54C	109.5
C34—O34—C341	117.44 (14)	H54B—C54—H54C	109.5

C5—N1—N2—C3	−1.01 (18)	C37—C31—C32—C33	−177.22 (16)
C5—N1—N2—C21	−178.66 (14)	C31—C32—C33—C34	−1.3 (3)
C3—N2—C21—C22	−25.9 (3)	C32—C33—C34—O34	179.87 (16)
N1—N2—C21—C22	151.18 (16)	C32—C33—C34—C35	0.4 (3)
C3—N2—C21—C26	155.84 (17)	C33—C34—O34—C341	5.1 (2)
N1—N2—C21—C26	−27.0 (2)	C35—C34—O34—C341	−175.37 (15)
C26—C21—C22—C23	−0.9 (3)	O34—C34—C35—C36	−178.71 (15)
N2—C21—C22—C23	−179.08 (16)	C33—C34—C35—C36	0.8 (3)
C21—C22—C23—C24	1.1 (3)	C34—C35—C36—C31	−1.2 (3)
C22—C23—C24—C25	−0.8 (3)	C32—C31—C36—C35	0.3 (2)
C23—C24—C25—C26	0.4 (3)	C37—C31—C36—C35	178.49 (16)
C24—C25—C26—C21	−0.2 (3)	N2—C3—C4—C5	−0.63 (19)
C22—C21—C26—C25	0.5 (3)	N3—C3—C4—C5	−174.66 (18)
N2—C21—C26—C25	178.70 (15)	N2—N1—C5—C4	0.59 (19)
N1—N2—C3—C4	1.04 (19)	N2—N1—C5—C51	−178.14 (15)
C21—N2—C3—C4	178.32 (16)	C3—C4—C5—N1	0.0 (2)
N1—N2—C3—N3	175.83 (14)	C3—C4—C5—C51	178.60 (17)
C21—N2—C3—N3	−6.9 (3)	N1—C5—C51—C54	−153.1 (2)
N2—C3—N3—C37	146.59 (16)	C4—C5—C51—C54	28.4 (3)
C4—C3—N3—C37	−40.1 (3)	N1—C5—C51—C52	−29.6 (2)
C3—N3—C37—C31	173.83 (15)	C4—C5—C51—C52	151.9 (2)
N3—C37—C31—C32	−11.9 (3)	N1—C5—C51—C53	87.9 (2)
N3—C37—C31—C36	170.00 (16)	C4—C5—C51—C53	−90.6 (2)
C36—C31—C32—C33	0.9 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C4—H4···O34ⁱ	0.95	2.59	3.487 (2)	157
C25—H25···Cg1ⁱⁱ	0.95	2.73	3.472 (2)	135

Symmetry codes: (i) −x+1, −y, −z; (ii) −x+1, y+1/2, −z+1/2.

Experimental details

Crystal data
Chemical formula	C₂₁H₂₃N₃O
M_r	333.42
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	120
a, b, c (Å)	10.0744 (3), 6.2583 (2), 28.9244 (9)
β (°)	101.0410 (13)
V (Å³)	1789.89 (10)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.08
Crystal size (mm)	0.40 × 0.20 × 0.10

Data collection
Diffractometer	Nonius KappaCCD diffractometer
Absorption correction	Multi-scan (DENZO–SMN; Otwinowski & Minor, 1997)
T_min, T_max	0.970, 0.992
No. of measured, independent and observed [I > 2σ(I)] reflections	9156, 3762, 2710
R_int	0.056
(sin θ/λ)_max (Å⁻¹)	0.649

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.052, 0.135, 1.04
No. of reflections	3762
No. of parameters	230
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.46, −0.33

Computer programs: KappaCCD Server Software (Nonius, 1997), DENZO–SMN (Otwinowski & Minor, 1997), DENZO–SMN, SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), ORTEPII (Johnson, 1976) and PLATON (Spek, 2002), SHELXL97 and WORDPERFECT macro PRPKAPPA (Ferguson, 1999).

Selected geometric parameters (Å, º) top

N1—C5	1.330 (2)	C3—N3	1.394 (2)
N1—N2	1.369 (2)	N3—C37	1.283 (2)
N2—C3	1.367 (2)	C37—C31	1.455 (2)
C3—C4	1.375 (2)	C4—C5	1.404 (2)

C5—N1—N2	105.23 (14)	C3—C4—C5	105.61 (16)
C3—N2—N1	111.23 (13)	N1—C5—C4	111.28 (15)
N2—C3—C4	106.64 (15)

C3—N2—C21—C22	−25.9 (3)	C3—N3—C37—C31	173.83 (15)
N1—N2—C21—C22	151.18 (16)	N3—C37—C31—C32	−11.9 (3)
C3—N2—C21—C26	155.84 (17)	N3—C37—C31—C36	170.00 (16)
N1—N2—C21—C26	−27.0 (2)	C33—C34—O34—C341	5.1 (2)
N2—C3—N3—C37	146.59 (16)	C35—C34—O34—C341	−175.37 (15)
C4—C3—N3—C37	−40.1 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C4—H4···O34ⁱ	0.95	2.59	3.487 (2)	157
C25—H25···Cg1ⁱⁱ	0.95	2.73	3.472 (2)	135

Symmetry codes: (i) −x+1, −y, −z; (ii) −x+1, y+1/2, −z+1/2.

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