2,4-Dichloro­benzaldehyde picolinoylhydrazone

The title mol­ecule, C₁₃H₉Cl₂N₃O, adopts a trans configuration with respect to the C=N double bond. There are two molecules in the asymmetric unit. The dihedral angles between the two rings are 17.2 (3) and 145.4 (3)°. The crystal structure is stabilized by inter­molecular N—H...O hydrogen bonds which link the mol­ecules into a chain structure.

Key indicators

• Single-crystal X-ray study
• T = 298 K
• Mean [sigma](C-C) = 0.004 Å
• R factor = 0.042
• wR factor = 0.098
• Data-to-parameter ratio = 13.3

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for        C24
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for         C2
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C15
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C17
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C22
PLAT431_ALERT_2_C Short Inter HL..A Contact  Cl2    ..  N4      ..       3.29 Ang.

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

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   6 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
   0 ALERT type 4 Improvement, methodology, query or suggestion

---

S1. Comment

Schiff base compounds have been of great interest for many years. These compounds play an important role in the development of coordination chemistry related to catalysis and enzymatic reactions (Brunner et al., 1983), magnetism and molecular architectures (Miller et al., 2000). The electron-withdrawing effect of the chlorine substituents in the dichlorobenzylidene unit may reduce the coordinating ability of the N atoms of the hydrazone. As an extension of work on the structural characterization of picolinohydrazone Schiff base compounds (Shao et al., 2004), we report here the crystal structure of (I), a new salicylhydrazone with 2,4-dichlorobenzaldehyde.

In the title compound, (I), which crystallizes with two unique molecules in the asymmetric unit (Fig. 1), the C—N bonds in the hydrazone units are characteristically short (Table 1) because of conjugation effects. All other bond lengths are within normal ranges (Allen et al., 1987). The dihedral angles between the pairs of benzene rings in each molecule are 17.2 (3)° (C1/C2/C3/C4/C5/C6 with C9/C10/C11/C12/C13/N3) and 145.4 (3)° (C14/C15/C16/C17/C18/C19 with C22/C23/C24/C25/C26/N6). The crystal structure is stabilized by intermolecular N—H···O hydrogen bonds (Table 2 and Fig. 2).

S2. Experimental

2,4-Dichlorobenzaldehyde (0.2 mmol, 35 mg) and picolinohydrazide (0.2 mmol, 27.4 mg) were dissolved in methanol (10 ml). The mixture was stirred at room temperature for 10 min. to give a clear yellow solution. The solution was set aside for 8 d. to allow slow evaporation of the solvent. Large colourless block-shaped crystals separated; these were collected and washed three times with water.

S3. Refinement

Atoms H2 and H5A were located in a difference Fourier map and their positions were refined freely with isotropic displacement parameters, giving distances N2—H2 0.854 (19) Å and N5—H5A 0.95 (2) Å. All other H atoms were placed in geometrically idealized positions (C—H 0.93 Å) and constrained to ride on their parent atoms with U_iso(H) = 1.2U_eq(C).

Computing details

Data collection: SMART (Bruker, 2002); cell refinement: SAINT (Bruker, 2002); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 2000); software used to prepare material for publication: SHELXL97.

Figures

	Fig. 1. The structure of (I), showing 30% probability displacement ellipsoids and the atom-numbering scheme.
	Fig. 2. The crystal packing of (I), viewed along the a axis. Dashed lines indicate intermolecular hydrogen bonds.

2,4-Dichlorobenzaldehyde picolinoylhydrazone

Crystal data

C13H9Cl2N3O	F(000) = 1200
Mr = 294.13	Dx = 1.462 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 1925 reflections
a = 10.500 (11) Å	θ = 4.6–39.8°
b = 17.763 (18) Å	µ = 0.48 mm^−1
c = 14.757 (15) Å	T = 298 K
β = 103.794 (14)°	Block, colourless
V = 2673 (5) Å^3	0.40 × 0.30 × 0.20 mm
Z = 8

Data collection

Bruker SMART APEX area-detector diffractometer	4662 independent reflections
Radiation source: fine-focus sealed tube	2532 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.036
ϕ and ω scans	θmax = 25.0°, θmin = 1.8°
Absorption correction: multi-scan (SADABS; Bruker, 2002)	h = −12→12
Tmin = 0.831, Tmax = 0.910	k = −20→18
14951 measured reflections	l = −17→7

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)] = 0.042	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.098	H atoms treated by a mixture of independent and constrained refinement
S = 0.86	w = 1/[σ^2(Fo^2) + (0.0453P)^2] where P = (Fo^2 + 2Fc^2)/3
4662 reflections	(Δ/σ)max = 0.001
351 parameters	Δρmax = 0.26 e Å^−3
0 restraints	Δρmin = −0.23 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
Cl1	0.60990 (8)	0.26040 (6)	0.77328 (5)	0.1118 (4)
Cl2	0.11780 (6)	0.20950 (5)	0.58473 (5)	0.0837 (3)
Cl3	0.98526 (8)	−0.00943 (5)	0.84983 (6)	0.1058 (3)
Cl4	0.62373 (10)	−0.08061 (5)	0.54437 (7)	0.1190 (4)
O1	0.78793 (15)	0.34118 (10)	0.36026 (12)	0.0699 (5)
O2	0.93330 (16)	0.36868 (10)	0.72803 (12)	0.0739 (6)
N1	0.69216 (18)	0.31731 (12)	0.51088 (15)	0.0548 (6)
N2	0.8176 (2)	0.34107 (12)	0.51667 (17)	0.0575 (6)
H2	0.8685 (19)	0.3497 (12)	0.5701 (14)	0.047 (7)*
N3	1.0534 (2)	0.40302 (13)	0.53949 (15)	0.0685 (7)
N4	0.95502 (18)	0.21837 (14)	0.74889 (14)	0.0573 (6)
N5	1.0505 (2)	0.26718 (14)	0.79340 (15)	0.0597 (6)
H5A	1.132 (2)	0.2493 (13)	0.8295 (15)	0.070 (8)*
N6	1.2617 (2)	0.35264 (14)	0.85374 (16)	0.0801 (7)
C1	0.5286 (2)	0.28335 (13)	0.58821 (16)	0.0485 (6)
C2	0.4936 (2)	0.26115 (14)	0.66864 (17)	0.0580 (7)
C3	0.3678 (2)	0.23952 (14)	0.66968 (17)	0.0621 (7)
H3	0.3468	0.2255	0.7250	0.074*
C4	0.2749 (2)	0.23930 (14)	0.58714 (18)	0.0555 (7)
C5	0.3043 (2)	0.26203 (16)	0.50649 (18)	0.0658 (8)
H5B	0.2395	0.2630	0.4512	0.079*
C6	0.4300 (2)	0.28347 (15)	0.50710 (17)	0.0630 (7)
H6	0.4495	0.2985	0.4515	0.076*
C7	0.6621 (2)	0.30586 (13)	0.58793 (18)	0.0556 (7)
H7	0.7246	0.3118	0.6439	0.067*
C8	0.8560 (2)	0.35431 (14)	0.4379 (2)	0.0539 (7)
C9	0.9880 (2)	0.38946 (14)	0.4517 (2)	0.0539 (7)
C10	1.0330 (2)	0.40863 (16)	0.3758 (2)	0.0696 (8)
H10	0.9848	0.3970	0.3160	0.083*
C11	1.1506 (3)	0.44537 (18)	0.3889 (2)	0.0855 (9)
H11	1.1831	0.4598	0.3382	0.103*
C12	1.2189 (3)	0.46041 (18)	0.4774 (3)	0.0854 (10)
H12	1.2986	0.4858	0.4884	0.103*
C13	1.1686 (3)	0.43769 (18)	0.5498 (2)	0.0797 (9)
H13	1.2175	0.4469	0.6102	0.096*
C14	0.8866 (2)	0.09309 (15)	0.71616 (17)	0.0544 (7)
C15	0.8839 (2)	0.01927 (17)	0.74561 (19)	0.0626 (7)
C16	0.8021 (3)	−0.03335 (16)	0.6946 (2)	0.0747 (8)
H16	0.8013	−0.0824	0.7164	0.090*
C17	0.7215 (3)	−0.01285 (18)	0.6111 (2)	0.0738 (8)
C18	0.7197 (3)	0.06002 (18)	0.5792 (2)	0.0792 (9)
H18	0.6633	0.0740	0.5231	0.095*
C19	0.8025 (2)	0.11133 (16)	0.63186 (18)	0.0703 (8)
H19	0.8022	0.1605	0.6101	0.084*
C20	0.9760 (2)	0.14867 (17)	0.76794 (17)	0.0583 (7)
H20	1.0479	0.1338	0.8145	0.070*
C21	1.0337 (2)	0.34125 (17)	0.77425 (17)	0.0581 (7)
C22	1.1524 (2)	0.38846 (17)	0.81344 (17)	0.0593 (7)
C23	1.1443 (3)	0.4640 (2)	0.8043 (2)	0.0949 (11)
H23	1.0648	0.4869	0.7769	0.114*
C24	1.2546 (4)	0.5064 (2)	0.8358 (2)	0.1121 (13)
H24	1.2515	0.5585	0.8287	0.134*
C25	1.3677 (3)	0.4721 (2)	0.8772 (2)	0.0930 (11)
H25	1.4438	0.4998	0.9001	0.112*
C26	1.3678 (3)	0.3957 (2)	0.8845 (2)	0.0979 (11)
H26	1.4463	0.3720	0.9125	0.117*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cl1	0.0970 (6)	0.1687 (9)	0.0539 (5)	−0.0513 (6)	−0.0133 (4)	0.0307 (5)
Cl2	0.0554 (4)	0.1048 (6)	0.0932 (6)	−0.0101 (4)	0.0223 (4)	0.0085 (5)
Cl3	0.0943 (6)	0.1027 (7)	0.1089 (7)	0.0037 (5)	0.0013 (5)	0.0367 (6)
Cl4	0.1300 (7)	0.0920 (7)	0.1309 (8)	−0.0390 (6)	0.0232 (6)	−0.0404 (6)
O1	0.0557 (10)	0.0956 (15)	0.0561 (12)	−0.0130 (10)	0.0090 (9)	−0.0083 (11)
O2	0.0612 (11)	0.0768 (14)	0.0714 (13)	−0.0010 (10)	−0.0083 (10)	0.0043 (11)
N1	0.0465 (12)	0.0615 (15)	0.0561 (14)	−0.0051 (11)	0.0113 (11)	−0.0020 (11)
N2	0.0439 (13)	0.0710 (16)	0.0550 (16)	−0.0115 (12)	0.0067 (12)	−0.0033 (13)
N3	0.0524 (13)	0.0803 (17)	0.0711 (16)	−0.0097 (13)	0.0112 (12)	−0.0102 (13)
N4	0.0487 (12)	0.0654 (16)	0.0558 (14)	−0.0067 (12)	0.0084 (10)	−0.0072 (12)
N5	0.0501 (13)	0.0601 (17)	0.0626 (15)	−0.0040 (13)	0.0005 (11)	−0.0048 (13)
N6	0.0580 (14)	0.0822 (18)	0.0904 (18)	−0.0056 (14)	−0.0014 (13)	−0.0061 (15)
C1	0.0498 (14)	0.0493 (16)	0.0461 (15)	−0.0032 (13)	0.0106 (12)	0.0012 (12)
C2	0.0620 (16)	0.0637 (19)	0.0453 (16)	−0.0125 (14)	0.0072 (13)	0.0028 (14)
C3	0.0700 (18)	0.069 (2)	0.0500 (17)	−0.0117 (15)	0.0204 (14)	0.0051 (14)
C4	0.0527 (15)	0.0596 (18)	0.0552 (17)	−0.0020 (13)	0.0150 (14)	−0.0009 (14)
C5	0.0505 (16)	0.095 (2)	0.0478 (16)	−0.0046 (15)	0.0039 (13)	−0.0011 (16)
C6	0.0588 (16)	0.087 (2)	0.0443 (15)	−0.0047 (16)	0.0140 (13)	0.0057 (14)
C7	0.0563 (16)	0.0541 (17)	0.0535 (17)	−0.0058 (13)	0.0075 (14)	−0.0022 (14)
C8	0.0477 (15)	0.0554 (18)	0.0594 (18)	0.0033 (13)	0.0142 (14)	0.0009 (14)
C9	0.0444 (14)	0.0498 (17)	0.0678 (19)	0.0025 (13)	0.0141 (14)	0.0016 (15)
C10	0.0549 (16)	0.079 (2)	0.075 (2)	−0.0051 (16)	0.0171 (15)	0.0043 (17)
C11	0.0667 (19)	0.105 (3)	0.090 (2)	−0.0088 (19)	0.0306 (18)	0.013 (2)
C12	0.0574 (18)	0.087 (3)	0.113 (3)	−0.0161 (17)	0.024 (2)	0.000 (2)
C13	0.0552 (17)	0.095 (2)	0.086 (2)	−0.0157 (17)	0.0104 (17)	−0.0137 (19)
C14	0.0465 (14)	0.0598 (19)	0.0588 (17)	0.0009 (14)	0.0162 (13)	−0.0054 (15)
C15	0.0503 (15)	0.068 (2)	0.0726 (19)	0.0040 (15)	0.0214 (14)	0.0045 (17)
C16	0.0740 (19)	0.0575 (19)	0.098 (2)	−0.0003 (17)	0.0300 (18)	0.0000 (18)
C17	0.0722 (19)	0.068 (2)	0.083 (2)	−0.0134 (17)	0.0222 (18)	−0.0211 (18)
C18	0.083 (2)	0.074 (2)	0.070 (2)	−0.0111 (19)	−0.0038 (16)	−0.0048 (18)
C19	0.0712 (18)	0.0603 (19)	0.0727 (19)	−0.0063 (16)	0.0041 (16)	−0.0048 (16)
C20	0.0471 (15)	0.070 (2)	0.0573 (17)	0.0037 (15)	0.0111 (12)	0.0000 (16)
C21	0.0544 (16)	0.070 (2)	0.0467 (16)	−0.0036 (16)	0.0061 (13)	−0.0051 (15)
C22	0.0612 (17)	0.064 (2)	0.0492 (16)	−0.0076 (16)	0.0072 (13)	−0.0014 (14)
C23	0.084 (2)	0.072 (2)	0.111 (3)	−0.014 (2)	−0.0109 (19)	0.009 (2)
C24	0.120 (3)	0.083 (3)	0.115 (3)	−0.032 (3)	−0.007 (2)	0.010 (2)
C25	0.086 (2)	0.108 (3)	0.082 (2)	−0.044 (2)	0.0129 (19)	−0.013 (2)
C26	0.0595 (19)	0.120 (3)	0.105 (3)	−0.011 (2)	0.0010 (18)	−0.008 (2)

Geometric parameters (Å, º)

Cl1—C2	1.726 (3)	C8—C9	1.490 (3)
Cl2—C4	1.724 (3)	C9—C10	1.359 (3)
Cl3—C15	1.725 (3)	C10—C11	1.369 (4)
Cl4—C17	1.730 (3)	C10—H10	0.9300
O1—C8	1.219 (3)	C11—C12	1.358 (4)
O2—C21	1.213 (3)	C11—H11	0.9300
N1—C7	1.267 (3)	C12—C13	1.361 (4)
N1—N2	1.366 (3)	C12—H12	0.9300
N2—C8	1.339 (3)	C13—H13	0.9300
N2—H2	0.854 (19)	C14—C19	1.382 (3)
N3—C13	1.333 (3)	C14—C15	1.384 (4)
N3—C9	1.335 (3)	C14—C20	1.448 (3)
N4—C20	1.277 (3)	C15—C16	1.367 (4)
N4—N5	1.369 (3)	C16—C17	1.367 (4)
N5—C21	1.348 (3)	C16—H16	0.9300
N5—H5A	0.95 (2)	C17—C18	1.376 (4)
N6—C22	1.323 (3)	C18—C19	1.367 (3)
N6—C26	1.338 (4)	C18—H18	0.9300
C1—C2	1.381 (3)	C19—H19	0.9300
C1—C6	1.383 (3)	C20—H20	0.9300
C1—C7	1.458 (3)	C21—C22	1.499 (3)
C2—C3	1.379 (3)	C22—C23	1.349 (4)
C3—C4	1.367 (3)	C23—C24	1.367 (4)
C3—H3	0.9300	C23—H23	0.9300
C4—C5	1.360 (3)	C24—C25	1.345 (4)
C5—C6	1.372 (3)	C24—H24	0.9300
C5—H5B	0.9300	C25—C26	1.363 (4)
C6—H6	0.9300	C25—H25	0.9300
C7—H7	0.9300	C26—H26	0.9300
C7—N1—N2	115.9 (2)	C11—C12—H12	120.6
C8—N2—N1	119.0 (2)	C13—C12—H12	120.6
C8—N2—H2	121.2 (15)	N3—C13—C12	123.9 (3)
N1—N2—H2	119.6 (15)	N3—C13—H13	118.0
C13—N3—C9	115.9 (3)	C12—C13—H13	118.0
C20—N4—N5	116.1 (2)	C19—C14—C15	116.7 (2)
C21—N5—N4	118.2 (2)	C19—C14—C20	120.7 (3)
C21—N5—H5A	120.0 (14)	C15—C14—C20	122.6 (2)
N4—N5—H5A	121.1 (14)	C16—C15—C14	122.1 (3)
C22—N6—C26	116.2 (3)	C16—C15—Cl3	117.5 (2)
C2—C1—C6	116.5 (2)	C14—C15—Cl3	120.4 (2)
C2—C1—C7	122.3 (2)	C17—C16—C15	119.1 (3)
C6—C1—C7	121.2 (2)	C17—C16—H16	120.4
C3—C2—C1	122.8 (2)	C15—C16—H16	120.4
C3—C2—Cl1	117.6 (2)	C16—C17—C18	121.0 (3)
C1—C2—Cl1	119.6 (2)	C16—C17—Cl4	118.9 (3)
C4—C3—C2	118.2 (2)	C18—C17—Cl4	120.1 (3)
C4—C3—H3	120.9	C19—C18—C17	118.5 (3)
C2—C3—H3	120.9	C19—C18—H18	120.7
C5—C4—C3	121.0 (2)	C17—C18—H18	120.7
C5—C4—Cl2	119.27 (19)	C18—C19—C14	122.6 (3)
C3—C4—Cl2	119.7 (2)	C18—C19—H19	118.7
C4—C5—C6	119.7 (2)	C14—C19—H19	118.7
C4—C5—H5B	120.1	N4—C20—C14	119.3 (2)
C6—C5—H5B	120.1	N4—C20—H20	120.4
C5—C6—C1	121.7 (2)	C14—C20—H20	120.4
C5—C6—H6	119.1	O2—C21—N5	124.2 (2)
C1—C6—H6	119.1	O2—C21—C22	121.6 (3)
N1—C7—C1	119.5 (2)	N5—C21—C22	114.2 (2)
N1—C7—H7	120.3	N6—C22—C23	123.4 (3)
C1—C7—H7	120.3	N6—C22—C21	117.2 (3)
O1—C8—N2	123.5 (2)	C23—C22—C21	119.4 (3)
O1—C8—C9	121.8 (3)	C22—C23—C24	119.1 (3)
N2—C8—C9	114.7 (2)	C22—C23—H23	120.5
N3—C9—C10	123.7 (2)	C24—C23—H23	120.5
N3—C9—C8	117.1 (3)	C25—C24—C23	119.3 (3)
C10—C9—C8	119.2 (3)	C25—C24—H24	120.3
C9—C10—C11	118.8 (3)	C23—C24—H24	120.3
C9—C10—H10	120.6	C24—C25—C26	118.1 (3)
C11—C10—H10	120.6	C24—C25—H25	120.9
C12—C11—C10	118.8 (3)	C26—C25—H25	120.9
C12—C11—H11	120.6	N6—C26—C25	123.9 (3)
C10—C11—H11	120.6	N6—C26—H26	118.0
C11—C12—C13	118.8 (3)	C25—C26—H26	118.0
C7—N1—N2—C8	−180.0 (2)	C11—C12—C13—N3	−2.0 (5)
C20—N4—N5—C21	178.9 (2)	C19—C14—C15—C16	−0.3 (4)
C6—C1—C2—C3	0.4 (4)	C20—C14—C15—C16	−177.8 (2)
C7—C1—C2—C3	−179.8 (2)	C19—C14—C15—Cl3	179.9 (2)
C6—C1—C2—Cl1	−179.2 (2)	C20—C14—C15—Cl3	2.4 (4)
C7—C1—C2—Cl1	0.6 (3)	C14—C15—C16—C17	1.0 (4)
C1—C2—C3—C4	0.8 (4)	Cl3—C15—C16—C17	−179.2 (2)
Cl1—C2—C3—C4	−179.5 (2)	C15—C16—C17—C18	−1.6 (4)
C2—C3—C4—C5	−2.0 (4)	C15—C16—C17—Cl4	177.1 (2)
C2—C3—C4—Cl2	177.7 (2)	C16—C17—C18—C19	1.5 (5)
C3—C4—C5—C6	1.9 (4)	Cl4—C17—C18—C19	−177.1 (2)
Cl2—C4—C5—C6	−177.8 (2)	C17—C18—C19—C14	−0.8 (5)
C4—C5—C6—C1	−0.6 (4)	C15—C14—C19—C18	0.2 (4)
C2—C1—C6—C5	−0.5 (4)	C20—C14—C19—C18	177.8 (3)
C7—C1—C6—C5	179.7 (2)	N5—N4—C20—C14	−173.3 (2)
N2—N1—C7—C1	177.5 (2)	C19—C14—C20—N4	17.9 (4)
C2—C1—C7—N1	171.9 (2)	C15—C14—C20—N4	−164.8 (2)
C6—C1—C7—N1	−8.3 (4)	N4—N5—C21—O2	8.4 (4)
N1—N2—C8—O1	−5.5 (4)	N4—N5—C21—C22	−170.2 (2)
N1—N2—C8—C9	172.3 (2)	C26—N6—C22—C23	−1.2 (4)
C13—N3—C9—C10	0.3 (4)	C26—N6—C22—C21	177.1 (3)
C13—N3—C9—C8	−177.0 (2)	O2—C21—C22—N6	−172.5 (2)
O1—C8—C9—N3	178.5 (2)	N5—C21—C22—N6	6.2 (3)
N2—C8—C9—N3	0.7 (3)	O2—C21—C22—C23	5.9 (4)
O1—C8—C9—C10	1.2 (4)	N5—C21—C22—C23	−175.4 (3)
N2—C8—C9—C10	−176.7 (2)	N6—C22—C23—C24	1.7 (5)
N3—C9—C10—C11	−1.5 (4)	C21—C22—C23—C24	−176.6 (3)
C8—C9—C10—C11	175.7 (2)	C22—C23—C24—C25	−1.6 (5)
C9—C10—C11—C12	0.9 (4)	C23—C24—C25—C26	1.1 (6)
C10—C11—C12—C13	0.7 (5)	C22—N6—C26—C25	0.7 (5)
C9—N3—C13—C12	1.5 (4)	C24—C25—C26—N6	−0.6 (6)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···O2	0.854 (19)	2.29 (2)	3.105 (4)	159.1 (19)
N5—H5A···O1^i	0.95 (2)	2.26 (2)	3.117 (4)	149.7 (19)

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