4 Methyl­aceto­phenone [(2 methyl 4 nitro 1H imidazol 1 yl)acet­yl]hydrazone

organic papers

o1126

15H17N5O3 doi:10.1107/S1600536806005794 Acta Cryst.(2006). E62, o1126–o1128

Acta Crystallographica Section E

Structure Reports Online

ISSN 1600-5368

4-Methylacetophenone

[(2-methyl-4-nitro-1H-imidazol-1-yl)acetyl]hydrazone

S. Balamurugan,a

A. Thiruvalluvara* and

Balakrishna Kallurayab

a_{Department of Physics, Rajah Serfoji Govt.}

College (Autonomous), Thanjavur 613 005, Tamil Nadu, India, andb_{Department of Studies} in Chemistry, Mangalore University,

Mangalagangothri 574 199, Karnataka, India

Correspondence e-mail: [email protected]

Key indicators

Single-crystal X-ray study T= 298 K

Mean(C–C) = 0.006 A˚ Rfactor = 0.065 wRfactor = 0.256

Data-to-parameter ratio = 14.0

For details of how these key indicators were automatically derived from the article, see http://journals.iucr.org/e.

Received 26 January 2006 Accepted 16 February 2006

#2006 International Union of Crystallography All rights reserved

In the title molecule, C15H17N5O3, the nitro group lies in the

plane of the imidazole group, which makes a dihedral angle of 59.9 (2) _{with the benzene ring. Intermolecular N—H O}

hydrogen bonds link the molecules into centrosymmetric dimers. The crystal packing is further stabilized by weak C—H O and C—H N interactions.

Comment

The imidazole nucleus appears in a number of naturally occurring products, among which the most important are the amino acid histidine and the base purine. Imidazole deriva-tives exhibit a broad spectrum of pharmacological activities, such as anticonvulsant (Vermaet al., 1974), anti-Parkinsonian (Naithani et al., 1989) and monoamine oxidase inhibitory (Harfenist et al., 1978) activities. To study the correlation between the effect of acethydrazone group substitution at position 1 of the imidazole ring and its geometry, the crystal structure of the title compound, (I), has been determined.

In (I) (Fig. 1), all bond lengths and angles (Table 1) are normal. The imidazole group is essentially planar and forms a dihedral angle of 59.9 (2) _{with the benzene ring. The nitro}

group lies in the plane of the imidazole group. In the crystal structure (Fig. 2), intermolecular N—H O hydrogen bonds (Table 2) link the molecules into centrosymmetric dimers. The packing is further stabilized by weak C—H O and C— H N interactions (Table 2).

Experimental

room temperature and poured into ice-cold water. The solid mass which separated was filtered off, dried and recrystallized from a mixture of ethanol and dimethylformamide (1:1). The yield of the isolated product was 58%.

Crystal data

C15H17N5O3

Mr= 315.34 Monoclinic,P2₁=c a= 8.423 (2) A˚

b= 10.577 (4) A˚

c= 17.97 (3) A˚

= 89.46 (8)

V= 1601 (3) A˚3

Z= 4

Dx= 1.308 Mg m

3

CuKradiation Cell parameters from 25

reflections

= 15–25

= 0.78 mm1

T= 298 (2) K Needle, colourless 0.30.10.1 mm

Data collection

Enraf–Nonius CAD-4 diffractometer

!–2scans

Absorption correction: scan (Northet al., 1968)

Tmin= 0.799,Tmax= 0.926

3111 measured reflections 2902 independent reflections 2512 reflections withI> 2(I)

Rint= 0.066

max= 68.0

h= 0!10

k= 0!12

l=21!21 2 standard reflections

frequency: 60 min intensity decay: none

Refinement

Refinement onF2

R[F2_{> 2(F}2_{)] = 0.065}

wR(F2) = 0.256

S= 1.14 2902 reflections 208 parameters

H-atom parameters constrained

w= 1/[2_(F

o2) + (0.1295P)2

+ 1.2895P] whereP= (Fo

2

+ 2Fc 2

)/3 (/)max< 0.001

max= 0.34 e A˚

3

min=0.20 e A˚

3

Table 1

Selected geometric parameters (A˚ ,_).

O12—C12 1.245 (4) O41—N4 1.222 (5) O42—N4 1.220 (5) N1—C2 1.369 (5) N1—C5 1.344 (5) N1—C11 1.453 (5)

N3—C2 1.319 (5) N3—C4 1.345 (5) N4—C4 1.434 (5) N13—N14 1.387 (5) N13—C12 1.342 (5) N14—C15 1.284 (5)

C2—N1—C5 108.4 (3) C2—N1—C11 126.8 (3) C5—N1—C11 124.0 (3) C2—N3—C4 104.9 (3) O41—N4—O42 123.4 (4) O41—N4—C4 117.7 (3) O42—N4—C4 118.9 (3) N14—N13—C12 119.2 (3) N13—N14—C15 116.7 (3) N1—C2—C24 123.3 (3) N1—C2—N3 110.2 (3)

N3—C2—C24 126.6 (3) N3—C4—C5 112.3 (3) N4—C4—C5 124.9 (3) N3—C4—N4 122.8 (3) N1—C5—C4 104.3 (3) N1—C11—C12 108.7 (3) O12—C12—N13 120.7 (3) N13—C12—C11 118.3 (3) O12—C12—C11 121.0 (3) N14—C15—C17 114.3 (3) N14—C15—C16 125.9 (3)

Table 2

Hydrogen-bond geometry (A˚ ,_).

D—H A D—H H A D A D—H A

N13—H13 O12i

0.86 2.03 2.858 (6) 162 C5—H5 O42ii

0.93 2.54 3.411 (7) 156 C11—H11A N3iii 0.97 2.45 3.397 (7) 165 C11—H11B O41ii

0.97 2.41 3.249 (7) 145 C24—H24A O42iii

0.96 2.58 3.318 (8) 134

Symmetry codes: (i) xþ1;yþ2;z; (ii) x;y1 2;zþ

1 2; (iii)

xþ1;y1 2;zþ

1 2.

The H atoms were positioned geometrically and allowed to ride on their parent atoms, with N—H = 0.86 A˚ , C—H = 0.93–0.97 A˚ andUiso = 1.2–1.5Ueq(parent atom).

Data collection: CAD-4 Software (Enraf–Nonius, 1989); cell refinement: CAD-4 Software; data reduction: XCAD4 (Farrugia, 1999); program(s) used to solve structure: SIR2004 (Burla et al., 2004); program(s) used to refine structure:SHELXL97(Sheldrick, 1997); molecular graphics:ORTEP-3(Farrugia, 1997); software used to prepare material for publication:PLATON(Spek, 2003).

organic papers

Acta Cryst.(2006). E62, o1126–o1128 Balamuruganet al. _C

15H17N5O3

o1127

View of (I) showing the atom-numbering scheme. Displacement ellipsoids are drawn at the 50% probability level.

Figure 2

The authors are grateful to Dr A. Babu Vargheese, Sophisticated Analytical Instrument Facility (SAIF), IIT– Madras, Chennai, for the X-ray data collection.

References

Burla, M. C., Caliandro, R., Camalli, M., Carrozzini, B., Cascarano, G. L., De Caro, L., Giacovazzo, C., Polidori, G. & Spagna, R. (2004). SIR2004. University of Bari, Italy.

Enraf–Nonius (1989).CAD-4 Software. Version 5. Enraf–Nonius, Delft, The Netherlands.

Farrugia, L. J. (1997).J. Appl. Cryst.30, 565. Farrugia, L. J. (1999).J. Appl. Cryst.32, 837–838.

Harfenist, M., Soroko, E. F. & Mekenzie, G. M. (1978).J. Med. Chem.21, 405– 409.

Naithani, P. K., Srivastava, V. K., Barthwal, J. P., Saxena, S. K., Gupta, T. K. & Shanker, K. (1989).Indian J. Chem. Sect B,28, 299–302.

North, A. C. T., Phillips, D. C. & Mathews, F. S. (1968).Acta Cryst.A24, 351– 359.

Sheldrick, G. M. (1997).SHELXL97. University of Go¨ttingen, Germany. Spek, A. L. (2003).J. Appl. Cryst.36, 7–13.

Verma, M., Chaturvedi, A. K., Chowdhari, A. & Parmar, S. S. (1974).J. Pharm. Sci.63, 1740–1747.

organic papers

o1128

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sup-1 Acta Cryst. (2006). E62, o1126–o1128

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Acta Cryst. (2006). E62, o1126–o1128 [https://doi.org/10.1107/S1600536806005794]

4-Methylacetophenone [(2-methyl-4-nitro-1

H

-imidazol-1-yl)acetyl]hydrazone

S. Balamurugan, A. Thiruvalluvar and Balakrishna Kalluraya

4-Methylacetophenone [(2-methyl-4-nitro-1H-imidazol-1-yl)acetyl]hydrazone

Crystal data

C15H17N5O3

Mr = 315.34

Monoclinic, P21/c

Hall symbol: -P 2ybc

a = 8.423 (2) Å

b = 10.577 (4) Å

c = 17.97 (3) Å

β = 89.46 (8)°

V = 1601 (3) Å3

Z = 4

F(000) = 664

Dx = 1.308 Mg m−3

Melting point = 524–525 K Cu Kα radiation, λ = 1.54180 Å Cell parameters from 25 reflections

θ = 15–25°

µ = 0.78 mm−1

T = 298 K Plate, colourless 0.3 × 0.1 × 0.1 mm

Data collection

Enraf–Nonius CAD-4 diffractometer

Radiation source: fine-focus sealed tube Graphite monochromator

ω–2θ scans

Absorption correction: ψ scan (North et al., 1968)

Tmin = 0.799, Tmax = 0.926

3111 measured reflections

2902 independent reflections 2512 reflections with I > 2σ(I)

Rint = 0.066

θmax = 68.0°, θmin = 4.9°

h = 0→10

k = 0→12

l = −21→21

2 standard reflections every 60 min intensity decay: none

Refinement

Refinement on F2

Least-squares matrix: full

R[F2 _{> 2σ(F}2_{)] = 0.065}

wR(F2_{) = 0.256}

S = 1.14 2902 reflections 208 parameters 0 restraints

Primary atom site location: structure-invariant direct methods

Secondary atom site location: difference Fourier map

Hydrogen site location: inferred from neighbouring sites

H-atom parameters constrained

w = 1/[σ2_(F

o2) + (0.1295P)2 + 1.2895P]

where P = (Fo2 + 2Fc2)/3

(Δ/σ)max < 0.001

Δρmax = 0.34 e Å−3

Δρmin = −0.20 e Å−3

Special details

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sup-2 Acta Cryst. (2006). E62, o1126–o1128

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

x y z Uiso*/Ueq

O12 0.4591 (4) 1.0360 (2) 0.08760 (15) 0.0761 (10) O41 −0.0500 (4) 1.2251 (3) 0.2636 (3) 0.1033 (16) O42 0.1268 (4) 1.3437 (3) 0.31357 (19) 0.0825 (11) N1 0.3216 (3) 0.9911 (2) 0.21945 (14) 0.0478 (8) N3 0.3600 (3) 1.1705 (3) 0.27901 (17) 0.0575 (10) N4 0.0868 (4) 1.2472 (3) 0.28163 (18) 0.0611 (10) N13 0.4002 (4) 0.8454 (3) 0.03981 (16) 0.0593 (10) N14 0.3374 (3) 0.7258 (2) 0.05162 (16) 0.0536 (9) C2 0.4307 (4) 1.0689 (3) 0.25197 (17) 0.0498 (10) C4 0.2055 (4) 1.1548 (3) 0.26327 (19) 0.0525 (11) C5 0.1775 (4) 1.0444 (3) 0.22681 (19) 0.0502 (10) C11 0.3546 (4) 0.8815 (3) 0.17312 (18) 0.0520 (10) C12 0.4085 (4) 0.9265 (3) 0.09706 (18) 0.0539 (10) C15 0.3305 (4) 0.6525 (3) −0.0052 (2) 0.0592 (11) C16 0.3859 (6) 0.6823 (4) −0.0796 (2) 0.0804 (18) C17 0.2593 (4) 0.5240 (3) 0.01097 (19) 0.0585 (11) C18 0.2877 (5) 0.4236 (4) −0.0378 (2) 0.0720 (14) C19 0.2214 (6) 0.3092 (4) −0.0232 (3) 0.0865 (18) C20 0.1185 (5) 0.2868 (3) 0.0385 (3) 0.0725 (15) C21 0.0926 (5) 0.3889 (4) 0.0839 (3) 0.0716 (14) C22 0.1591 (5) 0.5055 (3) 0.0710 (2) 0.0636 (11) C23 0.0406 (7) 0.1624 (4) 0.0473 (4) 0.102 (2) C24 0.6011 (5) 1.0395 (4) 0.2551 (3) 0.0750 (16) H5 0.08064 1.01301 0.21064 0.0602* H11A 0.43694 0.83032 0.19555 0.0623* H11B 0.25981 0.83010 0.16862 0.0623* H13 0.43347 0.86733 −0.00371 0.0713* H16A 0.49766 0.69985 −0.07857 0.1201* H16B 0.36662 0.61165 −0.11181 0.1201* H16C 0.33021 0.75506 −0.09768 0.1201* H18 0.35144 0.43504 −0.07978 0.0864* H19 0.24430 0.24228 −0.05519 0.1041* H21 0.02693 0.37881 0.12538 0.0861* H22 0.13630 0.57231 0.10303 0.0765* H23A 0.07799 0.10611 0.00903 0.1524* H23B 0.06537 0.12792 0.09519 0.1524* H23C −0.07231 0.17239 0.04325 0.1524* H24A 0.62064 0.95939 0.23157 0.1120* H24B 0.66027 1.10418 0.22965 0.1120* H24C 0.63366 1.03557 0.30611 0.1120*

Atomic displacement parameters (Å2₎

U11 _U22 _U33 _U12 _U13 _U23

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sup-3 Acta Cryst. (2006). E62, o1126–o1128

O41 0.0594 (18) 0.088 (2) 0.162 (4) 0.0102 (15) 0.0142 (19) −0.026 (2) O42 0.098 (2) 0.0545 (17) 0.095 (2) 0.0159 (14) 0.0031 (16) −0.0164 (15) N1 0.0620 (16) 0.0339 (13) 0.0473 (14) −0.0063 (11) 0.0037 (11) −0.0038 (10) N3 0.0639 (17) 0.0463 (16) 0.0621 (18) 0.0013 (12) 0.0037 (13) −0.0082 (13) N4 0.0696 (19) 0.0400 (16) 0.0734 (19) 0.0039 (13) 0.0100 (14) −0.0011 (14) N13 0.090 (2) 0.0371 (14) 0.0507 (16) −0.0131 (13) 0.0103 (14) −0.0089 (12) N14 0.0768 (18) 0.0319 (13) 0.0521 (15) −0.0008 (12) −0.0010 (13) 0.0007 (11) C2 0.0651 (18) 0.0395 (16) 0.0449 (16) −0.0009 (13) −0.0052 (13) 0.0038 (13) C4 0.0602 (19) 0.0397 (17) 0.0574 (19) 0.0003 (13) 0.0073 (14) −0.0028 (14) C5 0.0524 (17) 0.0400 (16) 0.0579 (18) −0.0064 (13) 0.0062 (13) 0.0024 (14) C11 0.070 (2) 0.0378 (16) 0.0482 (17) −0.0047 (14) 0.0043 (14) 0.0008 (13) C12 0.078 (2) 0.0329 (16) 0.0507 (18) −0.0032 (14) 0.0087 (15) −0.0033 (13) C15 0.076 (2) 0.0469 (19) 0.0546 (19) 0.0000 (15) −0.0034 (16) −0.0097 (15) C16 0.123 (4) 0.072 (3) 0.046 (2) −0.012 (2) 0.001 (2) −0.0156 (18) C17 0.077 (2) 0.0494 (19) 0.0493 (18) 0.0018 (16) −0.0131 (16) −0.0085 (15) C18 0.097 (3) 0.049 (2) 0.070 (2) 0.0100 (19) −0.010 (2) −0.0082 (18) C19 0.106 (3) 0.051 (2) 0.103 (4) 0.004 (2) −0.029 (3) −0.020 (2) C20 0.099 (3) 0.0332 (18) 0.086 (3) −0.0009 (17) −0.036 (2) −0.0040 (17) C21 0.092 (3) 0.049 (2) 0.074 (2) −0.0074 (19) −0.016 (2) −0.0005 (19) C22 0.080 (2) 0.0417 (18) 0.069 (2) 0.0021 (16) −0.0048 (18) −0.0064 (16) C23 0.141 (5) 0.037 (2) 0.128 (4) −0.011 (2) −0.040 (4) 0.003 (2) C24 0.067 (2) 0.068 (3) 0.090 (3) 0.0099 (18) −0.006 (2) −0.023 (2)

Geometric parameters (Å, º)

O12—C12 1.245 (4) C19—C20 1.421 (8) O41—N4 1.222 (5) C20—C23 1.478 (6) O42—N4 1.220 (5) C20—C21 1.370 (7) N1—C2 1.369 (5) C21—C22 1.373 (6) N1—C5 1.344 (5) C5—H5 0.9300 N1—C11 1.453 (5) C11—H11A 0.9700 N3—C2 1.319 (5) C11—H11B 0.9700 N3—C4 1.345 (5) C16—H16A 0.9600 N4—C4 1.434 (5) C16—H16B 0.9600 N13—N14 1.387 (5) C16—H16C 0.9600 N13—C12 1.342 (5) C18—H18 0.9300 N14—C15 1.284 (5) C19—H19 0.9300 N13—H13 0.8600 C21—H21 0.9300 C2—C24 1.470 (6) C22—H22 0.9300 C4—C5 1.361 (5) C23—H23A 0.9600 C11—C12 1.513 (5) C23—H23B 0.9600 C15—C16 1.447 (6) C23—H23C 0.9600 C15—C17 1.513 (5) C24—H24A 0.9600 C17—C22 1.377 (6) C24—H24B 0.9600 C17—C18 1.396 (6) C24—H24C 0.9600 C18—C19 1.357 (7)

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sup-4 Acta Cryst. (2006). E62, o1126–o1128

O12···C2 2.982 (6) C19···H16Aviii _3.0100

O12···C24 3.250 (8) C22···H24Cvii _2.8500

O12···N13i _{2.858 (6) C24···H11A 2.8200}

O12···C16i _{3.256 (7) H5···O41 2.6700}

O41···C11ii _{3.249 (7) H5···H11B 2.5600}

O42···N3 2.753 (6) H5···H23Bx _2.4100

O42···C5ii _{3.411 (7) H5···O42}vi _2.5400

O42···C24iii _{3.318 (8) H11A···N14 2.9400}

O12···H16Ci _{2.8400 H11A···C24 2.8200}

O12···H13i _{2.0300 H11A···H24A 2.1700}

O12···H16Ai _{2.8200 H11A···N3}vii _2.4500

O41···H5 2.6700 H11B···N14 2.4600 O41···H24Biv _{2.8300 H11B···H5 2.5600}

O41···H11Bii _{2.4100 H11B···O41}vi _2.4100

O42···H5ii _{2.5400 H13···C16 2.4200}

O42···H24Aiii _{2.5800 H13···H16A 2.2900}

O42···H19v _{2.7200 H13···H16C 2.2500}

N1···O12 2.670 (6) H13···O12i _2.0300

N3···O42 2.753 (6) H13···C12i _3.0500

N3···C11iii _{3.397 (7) H16A···N13 2.7500}

N13···O12i _{2.858 (6) H16A···H13 2.2900}

N3···H11Aiii _{2.4500 H16A···O12}i _2.8200

N3···H18v _{2.7700 H16A···C18}viii _3.0700

N13···H16A 2.7500 H16A···C19viii _3.0100

N13···H16C 2.7200 H16B···C18 2.4800 N14···H11A 2.9400 H16B···H18 1.9600 N14···H11B 2.4600 H16C···N13 2.7200 N14···H22 2.5200 H16C···H13 2.2500 C2···O12 2.982 (6) H16C···O12i _2.8400

C5···O42vi _{3.411 (7) H16C···H23C}ix _2.4900

C11···O41vi _{3.249 (7) H18···C16 2.6300}

C11···N3vii _{3.397 (7) H18···H16B 1.9600}

C12···C24 3.495 (8) H18···N3xi _2.7700

C15···C18viii _{3.411 (8) H18···C2}xi _3.0900

C16···O12i _{3.256 (7) H19···H23A 2.3100}

C17···C21ix _{3.555 (8) H19···O42}xi _2.7200

C18···C15viii _{3.411 (8) H22···N14 2.5200}

C21···C17ix _{3.555 (8) H22···H24C}vii _2.5800

C24···O12 3.250 (8) H23A···H19 2.3100 C24···C12 3.495 (8) H23B···C5xii _2.7000

C24···O42vii _{3.318 (8) H23B···H5}xii _2.4100

C2···H18v _{3.0900 H23C···C15}ix _2.9400

C5···H23Bx _{2.7000 H23C···H16C}ix _2.4900

C11···H24A 2.6200 H24A···C11 2.6200 C12···H13i _{3.0500 H24A···C12 3.0400}

C12···H24A 3.0400 H24A···H11A 2.1700 C15···H23Cix _{2.9400 H24A···O42}vii _2.5800

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sup-5 Acta Cryst. (2006). E62, o1126–o1128

C16···H18 2.6300 H24C···C22iii _2.8500

C18···H16Aviii _{3.0700 H24C···H22}iii _2.5800

C2—N1—C5 108.4 (3) C17—C22—C21 120.4 (4) C2—N1—C11 126.8 (3) N1—C5—H5 128.00 C5—N1—C11 124.0 (3) C4—C5—H5 128.00 C2—N3—C4 104.9 (3) N1—C11—H11A 110.00 O41—N4—O42 123.4 (4) N1—C11—H11B 110.00 O41—N4—C4 117.7 (3) C12—C11—H11A 110.00 O42—N4—C4 118.9 (3) C12—C11—H11B 110.00 N14—N13—C12 119.2 (3) H11A—C11—H11B 108.00 N13—N14—C15 116.7 (3) C15—C16—H16A 109.00 C12—N13—H13 120.00 C15—C16—H16B 109.00 N14—N13—H13 120.00 C15—C16—H16C 109.00 N1—C2—C24 123.3 (3) H16A—C16—H16B 109.00 N1—C2—N3 110.2 (3) H16A—C16—H16C 110.00 N3—C2—C24 126.6 (3) H16B—C16—H16C 110.00 N3—C4—C5 112.3 (3) C17—C18—H18 120.00 N4—C4—C5 124.9 (3) C19—C18—H18 120.00 N3—C4—N4 122.8 (3) C18—C19—H19 118.00 N1—C5—C4 104.3 (3) C20—C19—H19 118.00 N1—C11—C12 108.7 (3) C20—C21—H21 118.00 O12—C12—N13 120.7 (3) C22—C21—H21 118.00 N13—C12—C11 118.3 (3) C17—C22—H22 120.00 O12—C12—C11 121.0 (3) C21—C22—H22 120.00 N14—C15—C17 114.3 (3) C20—C23—H23A 109.00 C16—C15—C17 119.8 (3) C20—C23—H23B 110.00 N14—C15—C16 125.9 (3) C20—C23—H23C 109.00 C18—C17—C22 118.9 (3) H23A—C23—H23B 110.00 C15—C17—C18 119.8 (3) H23A—C23—H23C 109.00 C15—C17—C22 121.1 (3) H23B—C23—H23C 109.00 C17—C18—C19 119.3 (4) C2—C24—H24A 109.00 C18—C19—C20 123.1 (4) C2—C24—H24B 109.00 C19—C20—C23 119.9 (4) C2—C24—H24C 109.00 C19—C20—C21 115.2 (4) H24A—C24—H24B 109.00 C21—C20—C23 124.8 (5) H24A—C24—H24C 109.00 C20—C21—C22 123.0 (4) H24B—C24—H24C 110.00

supporting information

sup-6 Acta Cryst. (2006). E62, o1126–o1128

C2—N3—C4—N4 −178.2 (3) C22—C17—C18—C19 −2.7 (6) C2—N3—C4—C5 0.2 (4) C18—C17—C22—C21 2.2 (6) O41—N4—C4—N3 178.6 (4) C15—C17—C22—C21 178.5 (4) O41—N4—C4—C5 0.4 (6) C17—C18—C19—C20 2.4 (7) O42—N4—C4—N3 −0.8 (5) C18—C19—C20—C23 175.0 (5) O42—N4—C4—C5 −178.9 (4) C18—C19—C20—C21 −1.3 (7) C12—N13—N14—C15 179.2 (3) C19—C20—C21—C22 0.7 (7) N14—N13—C12—O12 −177.5 (3) C23—C20—C21—C22 −175.5 (5) N14—N13—C12—C11 2.4 (5) C20—C21—C22—C17 −1.2 (7) N13—N14—C15—C16 1.7 (5)

Symmetry codes: (i) −x+1, −y+2, −z; (ii) −x, y+1/2, −z+1/2; (iii) −x+1, y+1/2, −z+1/2; (iv) x−1, y, z; (v) x, −y+3/2, z+1/2; (vi) −x, y−1/2, −z+1/2; (vii) −x+1, y−1/2, −z+1/2; (viii) −x+1, −y+1, −z; (ix) −x, −y+1, −z; (x) x, y+1, z; (xi) x, −y+3/2, z−1/2; (xii) x, y−1, z; (xiii) x+1, y, z.

Hydrogen-bond geometry (Å, º)

D—H···A D—H H···A D···A D—H···A

N13—H13···O12i _{0.86 2.03 2.858 (6) 162}

C5—H5···O42vi _{0.93 2.54 3.411 (7) 156}

C11—H11A···N3vii _{0.97 2.45 3.397 (7) 165}

C11—H11B···O41vi _{0.97 2.41 3.249 (7) 145}

C24—H24A···O42vii _{0.96 2.58 3.318 (8) 134}