3,5-Dinitro-N-(tri-2-pyridylmeth­yl)benzamide

The title compound, C₂₃H₁₆N₆O₅, was synthesized by reaction of tri-2-pyridylmethyl­amine and 3,5-dinitro­benzoyl chloride. There is an intra­molecular N—H...N hydrogen bond [N...N = 2.5740 (12) Å] between the amide group and one of the three pyridine rings. The crystal packing is stabilized by weak inter­molecular C—H...O hydrogen bonds.

Key indicators

• Single-crystal X-ray study
• T = 100 K
• Mean [sigma](C-C)= 0.001 Å
• R factor = 0.037
• wR factor = 0.099
• Data-to-parameter ratio = 19.1

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S1. Comment

Tripodal ligands based on nitrogen heterocycles have secured an important place in inorganic chemistry. Ligands of this type reported to date can broadly be divided into two classes: those in which the arms of the tripod are connected via methylene linking groups to a teriary amine function, which is itself generally involved in coordination, and those in which the centeral linking atom does not coordinate to the metal for chemical or geometric reasons. An example of the first class is furnished by tris- (2-pyridyl-methyl) amine(tpm) and its derivatives, whose copper complexes have been extensively studied (Jacobson et al.,1988, 1991, Lee et al., 1995, Tyekler et al., 1989, Wei et al.,1994). The structure determnation of the title compound, C₂₃H₁₆N₆O₅, was undertaken as part of our studies on tpm derivaties. The crystal structure of free 3,5-dinitro-N-(tri-pyridin-2yl-methyl)-benzamide is shown in Fig.1. The only sp³ carbon atom in the molecule, C8, has a distorted tetrahedral geometry with bond angles range from 105.82 (7) to 115.50 (8)°. The benzamide part of the molecule is nearly laying in a plane, but three pyridine rings make angles of 15.87 (5), 70.06 (5), and 75.70 (5)° with the plane of phenyl ring, giving a propeller-type geometry. From the two nitro groups, one is almost laying in the same plane with benzamide and the other is rotated out of this plane by angle of 29.25°, because of intermolecular van der Waals repulsion between two nitro groups in the packing of molecules (Fig. 2). The main point of interest in the structure is the intramolecular hydrogen bonding between the amido hydrogen atom and one of the pyridine rings (Fig. 3), N1—H1N···N4 [N1···N4 2.5740 (12) Å]. The packing of molecules in the solid state is stabilized by C—H···O intermolecular interactions with C···O distances range from 3.2522 (15) to 3.4414 (13) Å. There are also C—H···π intermolecular interactions, with H···π distances of 3.026 and 3.046 Å which take part in stabilization of molecular packing (Fig. 4).

Related literature

For reversible O₂ binding to copper(I) complexes with tripodal ligands, see: Lee et al. (1995), Jacobson et al. (1988) and Tyekler et al. (1989). For fluoride as a terminal and a bridging ligand in Cu(II)[tris- (2-pyridyl-methyl) amine] complexes, see: Jacobson et al. (1991). For the chemistry of LCu(II)Cl complexes with a quinolyl-containing tripodal teradentate ligand L, see: Wei et al. (1994).

S2. Experimental

To a solution of tris(2-pyridyl)methylamine (0.5 g, 1.9 mmol) and triethylamine (3.6 mmol) in THF(14 ml) was added 3,5-dinitrobenzoylchloride (0.58, 2.5 mmol). After stirring at 4–5°C for 2 h, the precipitate was filtered off, washed with water and recrystallized from ethanol as title compound(I), 3,5-dinitro-N-(tri-pyridin-2yl-methyl)-benzamide (0.87 g, 95%). mp: 220°C; IR: 3326, 1680, 1586, 1541, 1501, 1345 cm^-1.

S3. Refinement

The hydrogen atom of NH-group was localized in difference Fourier synthesis and placed in idealized position (N—H 0.89 Å). The C-bound H atoms were placed in calculated positions (C—H 0.95 Å). All H atoms were refined in riding model approximation, with U_iso(H) = 1.2Ueq of the parent atom.

Computing details

Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT-Plus (Bruker, 2001); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXTL (Sheldrick, 2001); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Figures

	Fig. 1. The molecular structure of (I), with displacement ellipsoids drawn at the 50% probability level.
	Fig. 2. Intermolecular van der Waals repulsion between two nitro groups.
	Fig. 3. The crystal packing of (I), hydrogen bond are shown as dashed lines.
	Fig. 4. C—H···π stacking interactions between two aromatic rings.

3,5-Dinitro-N-(tri-2-pyridylmethyl)benzamide

Crystal data

C23H16N6O5	F(000) = 944
Mr = 456.42	Dx = 1.500 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 5259 reflections
a = 14.7680 (7) Å	θ = 2.7–30.0°
b = 8.4109 (5) Å	µ = 0.11 mm^−1
c = 16.7738 (9) Å	T = 100 K
β = 104.015 (5)°	Prism, light-brown
V = 2021.49 (19) Å^3	0.30 × 0.20 × 0.20 mm
Z = 4

Data collection

Bruker SMART APEXII CCD area-detector diffractometer	5854 independent reflections
Radiation source: fine-focus sealed tube	5015 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.025
φ and ω scans	θmax = 30.0°, θmin = 1.7°
Absorption correction: multi-scan (SADABS; Sheldrick, 2003)	h = −20→20
Tmin = 0.970, Tmax = 0.980	k = −11→11
25445 measured reflections	l = −23→23

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)] = 0.037	Hydrogen site location: difference Fourier map
wR(F^2) = 0.099	H-atom parameters constrained
S = 1.01	w = 1/[σ^2(Fo^2) + (0.055P)^2 + 0.7P] where P = (Fo^2 + 2Fc^2)/3
5854 reflections	(Δ/σ)max < 0.001
307 parameters	Δρmax = 0.36 e Å^−3
0 restraints	Δρmin = −0.27 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
O1	0.01748 (5)	0.45777 (9)	0.20406 (4)	0.01672 (15)
O2	−0.14768 (5)	0.63598 (9)	0.50628 (5)	0.01808 (15)
O3	−0.15869 (6)	0.40284 (10)	0.55897 (5)	0.02180 (17)
O4	−0.06772 (5)	−0.06810 (9)	0.42580 (4)	0.01746 (15)
O5	0.04774 (6)	−0.02392 (9)	0.36962 (5)	0.02059 (16)
N1	−0.05234 (6)	0.67856 (9)	0.23889 (5)	0.01250 (15)
H1N	−0.0882	0.7203	0.2687	0.015*
N2	−0.13867 (6)	0.49091 (10)	0.50740 (5)	0.01297 (15)
N3	−0.01847 (6)	0.02066 (10)	0.39573 (5)	0.01351 (16)
N4	−0.14713 (6)	0.93786 (10)	0.22800 (5)	0.01410 (16)
N5	−0.17659 (6)	0.62099 (10)	0.09365 (5)	0.01511 (16)
N6	0.07998 (6)	0.89062 (12)	0.11185 (5)	0.01994 (18)
C1	−0.02372 (6)	0.52656 (11)	0.24925 (6)	0.01213 (17)
C2	−0.04297 (6)	0.44040 (11)	0.32212 (5)	0.01106 (16)
C3	−0.08127 (6)	0.51175 (11)	0.38158 (5)	0.01169 (17)
H3A	−0.0941	0.6225	0.3799	0.014*
C4	−0.10011 (6)	0.41669 (11)	0.44326 (5)	0.01135 (17)
C5	−0.08273 (6)	0.25483 (11)	0.44912 (5)	0.01207 (17)
H5A	−0.0985	0.1914	0.4906	0.014*
C6	−0.04106 (6)	0.19097 (11)	0.39097 (6)	0.01175 (17)
C7	−0.02000 (6)	0.27899 (11)	0.32824 (6)	0.01204 (17)
H7A	0.0095	0.2306	0.2900	0.014*
C8	−0.04345 (6)	0.77199 (11)	0.16808 (6)	0.01216 (17)
C9	−0.09891 (7)	0.92740 (11)	0.17038 (6)	0.01290 (17)
C10	−0.09967 (8)	1.04672 (12)	0.11226 (6)	0.01803 (19)
H10A	−0.0652	1.0353	0.0716	0.022*
C11	−0.15204 (8)	1.18218 (12)	0.11546 (7)	0.0207 (2)
H11A	−0.1532	1.2661	0.0773	0.025*
C12	−0.20278 (7)	1.19435 (12)	0.17478 (7)	0.0190 (2)
H12A	−0.2395	1.2859	0.1777	0.023*
C13	−0.19856 (7)	1.06983 (12)	0.22969 (6)	0.01668 (19)
H13A	−0.2334	1.0778	0.2703	0.020*
C14	−0.09476 (7)	0.68403 (11)	0.08846 (6)	0.01280 (17)
C15	−0.06228 (7)	0.67416 (13)	0.01756 (6)	0.0190 (2)
H15A	−0.0046	0.7217	0.0153	0.023*
C16	−0.11560 (8)	0.59356 (14)	−0.05022 (6)	0.0222 (2)
H16A	−0.0945	0.5844	−0.0992	0.027*
C17	−0.19969 (8)	0.52701 (13)	−0.04524 (6)	0.0197 (2)
H17A	−0.2376	0.4714	−0.0905	0.024*
C18	−0.22687 (7)	0.54382 (12)	0.02769 (6)	0.01676 (19)
H18A	−0.2846	0.4980	0.0312	0.020*
C19	0.06044 (7)	0.81051 (11)	0.17469 (6)	0.01321 (17)
C20	0.12964 (7)	0.76865 (12)	0.24395 (6)	0.01549 (18)
H20A	0.1139	0.7155	0.2887	0.019*
C21	0.22193 (7)	0.80587 (13)	0.24646 (6)	0.0189 (2)
H21A	0.2703	0.7764	0.2926	0.023*
C22	0.24271 (7)	0.88634 (14)	0.18117 (7)	0.0205 (2)
H22A	0.3053	0.9124	0.1811	0.025*
C23	0.16932 (8)	0.92757 (14)	0.11598 (7)	0.0225 (2)
H23A	0.1830	0.9853	0.0717	0.027*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0228 (4)	0.0149 (3)	0.0155 (3)	0.0031 (3)	0.0106 (3)	0.0018 (3)
O2	0.0229 (4)	0.0136 (3)	0.0192 (3)	0.0030 (3)	0.0080 (3)	−0.0013 (3)
O3	0.0298 (4)	0.0211 (4)	0.0198 (4)	0.0038 (3)	0.0164 (3)	0.0052 (3)
O4	0.0233 (4)	0.0122 (3)	0.0178 (3)	−0.0019 (3)	0.0068 (3)	0.0027 (3)
O5	0.0250 (4)	0.0162 (3)	0.0238 (4)	0.0062 (3)	0.0121 (3)	0.0019 (3)
N1	0.0159 (4)	0.0119 (4)	0.0115 (3)	0.0022 (3)	0.0068 (3)	0.0034 (3)
N2	0.0130 (3)	0.0148 (4)	0.0119 (3)	0.0014 (3)	0.0045 (3)	0.0005 (3)
N3	0.0185 (4)	0.0106 (3)	0.0113 (3)	0.0015 (3)	0.0033 (3)	0.0007 (3)
N4	0.0130 (4)	0.0143 (4)	0.0148 (4)	0.0011 (3)	0.0029 (3)	−0.0004 (3)
N5	0.0156 (4)	0.0138 (4)	0.0169 (4)	0.0004 (3)	0.0058 (3)	0.0006 (3)
N6	0.0169 (4)	0.0253 (5)	0.0179 (4)	−0.0031 (3)	0.0048 (3)	0.0076 (3)
C1	0.0137 (4)	0.0122 (4)	0.0109 (4)	−0.0008 (3)	0.0037 (3)	0.0016 (3)
C2	0.0117 (4)	0.0113 (4)	0.0103 (4)	−0.0003 (3)	0.0029 (3)	0.0014 (3)
C3	0.0116 (4)	0.0114 (4)	0.0119 (4)	0.0002 (3)	0.0025 (3)	0.0007 (3)
C4	0.0112 (4)	0.0128 (4)	0.0106 (4)	0.0006 (3)	0.0036 (3)	−0.0004 (3)
C5	0.0126 (4)	0.0124 (4)	0.0113 (4)	−0.0004 (3)	0.0032 (3)	0.0014 (3)
C6	0.0139 (4)	0.0087 (4)	0.0124 (4)	0.0006 (3)	0.0028 (3)	0.0008 (3)
C7	0.0132 (4)	0.0119 (4)	0.0111 (4)	−0.0002 (3)	0.0031 (3)	0.0000 (3)
C8	0.0141 (4)	0.0117 (4)	0.0117 (4)	0.0011 (3)	0.0050 (3)	0.0034 (3)
C9	0.0138 (4)	0.0120 (4)	0.0125 (4)	0.0004 (3)	0.0024 (3)	0.0009 (3)
C10	0.0229 (5)	0.0154 (4)	0.0163 (4)	0.0017 (4)	0.0057 (4)	0.0040 (4)
C11	0.0247 (5)	0.0141 (4)	0.0217 (5)	0.0027 (4)	0.0023 (4)	0.0049 (4)
C12	0.0171 (4)	0.0130 (4)	0.0241 (5)	0.0030 (3)	−0.0005 (4)	−0.0022 (4)
C13	0.0136 (4)	0.0172 (4)	0.0183 (4)	0.0013 (3)	0.0019 (3)	−0.0032 (4)
C14	0.0146 (4)	0.0116 (4)	0.0124 (4)	0.0025 (3)	0.0038 (3)	0.0025 (3)
C15	0.0176 (4)	0.0260 (5)	0.0151 (4)	−0.0003 (4)	0.0071 (4)	0.0013 (4)
C16	0.0236 (5)	0.0305 (6)	0.0134 (4)	0.0025 (4)	0.0061 (4)	−0.0009 (4)
C17	0.0208 (5)	0.0199 (5)	0.0163 (4)	0.0034 (4)	0.0005 (4)	−0.0021 (4)
C18	0.0149 (4)	0.0144 (4)	0.0202 (5)	0.0014 (3)	0.0028 (4)	0.0004 (3)
C19	0.0144 (4)	0.0126 (4)	0.0135 (4)	−0.0003 (3)	0.0051 (3)	0.0011 (3)
C20	0.0174 (4)	0.0159 (4)	0.0135 (4)	−0.0003 (3)	0.0044 (3)	0.0017 (3)
C21	0.0163 (4)	0.0206 (5)	0.0180 (5)	−0.0016 (4)	0.0008 (4)	0.0001 (4)
C22	0.0162 (4)	0.0241 (5)	0.0218 (5)	−0.0051 (4)	0.0057 (4)	−0.0002 (4)
C23	0.0194 (5)	0.0297 (6)	0.0195 (5)	−0.0068 (4)	0.0070 (4)	0.0056 (4)

Geometric parameters (Å, º)

O1—C1	1.2260 (11)	C8—C9	1.5480 (13)
O2—N2	1.2271 (11)	C8—C14	1.5540 (13)
O3—N2	1.2281 (11)	C9—C10	1.3973 (13)
O4—N3	1.2323 (11)	C10—C11	1.3854 (15)
O5—N3	1.2230 (11)	C10—H10A	0.9500
N1—C1	1.3445 (12)	C11—C12	1.3867 (16)
N1—C8	1.4564 (11)	C11—H11A	0.9500
N1—H1N	0.8853	C12—C13	1.3860 (15)
N2—C4	1.4723 (12)	C12—H12A	0.9500
N3—C6	1.4686 (12)	C13—H13A	0.9500
N4—C9	1.3352 (12)	C14—C15	1.3885 (13)
N4—C13	1.3491 (13)	C15—C16	1.3924 (15)
N5—C18	1.3412 (13)	C15—H15A	0.9500
N5—C14	1.3417 (12)	C16—C17	1.3829 (16)
N6—C19	1.3401 (12)	C16—H16A	0.9500
N6—C23	1.3407 (13)	C17—C18	1.3840 (15)
C1—C2	1.5061 (12)	C17—H17A	0.9500
C2—C3	1.3957 (12)	C18—H18A	0.9500
C2—C7	1.3971 (13)	C19—C20	1.3939 (13)
C3—C4	1.3880 (12)	C20—C21	1.3891 (14)
C3—H3A	0.9500	C20—H20A	0.9500
C4—C5	1.3845 (13)	C21—C22	1.3836 (15)
C5—C6	1.3818 (13)	C21—H21A	0.9500
C5—H5A	0.9500	C22—C23	1.3844 (15)
C6—C7	1.3821 (12)	C22—H22A	0.9500
C7—H7A	0.9500	C23—H23A	0.9500
C8—C19	1.5454 (13)
C1—N1—C8	122.07 (8)	C11—C10—C9	118.28 (10)
C1—N1—H1N	121.1	C11—C10—H10A	120.9
C8—N1—H1N	115.6	C9—C10—H10A	120.9
O2—N2—O3	124.52 (8)	C10—C11—C12	119.49 (10)
O2—N2—C4	118.04 (8)	C10—C11—H11A	120.3
O3—N2—C4	117.43 (8)	C12—C11—H11A	120.3
O5—N3—O4	124.28 (8)	C13—C12—C11	118.41 (9)
O5—N3—C6	118.05 (8)	C13—C12—H12A	120.8
O4—N3—C6	117.67 (8)	C11—C12—H12A	120.8
C9—N4—C13	118.10 (9)	N4—C13—C12	122.87 (10)
C18—N5—C14	117.72 (9)	N4—C13—H13A	118.6
C19—N6—C23	118.20 (9)	C12—C13—H13A	118.6
O1—C1—N1	123.80 (8)	N5—C14—C15	122.37 (9)
O1—C1—C2	119.62 (8)	N5—C14—C8	113.07 (8)
N1—C1—C2	116.57 (8)	C15—C14—C8	124.53 (9)
C3—C2—C7	119.90 (8)	C14—C15—C16	118.95 (10)
C3—C2—C1	124.19 (8)	C14—C15—H15A	120.5
C7—C2—C1	115.91 (8)	C16—C15—H15A	120.5
C4—C3—C2	118.30 (8)	C17—C16—C15	119.10 (10)
C4—C3—H3A	120.9	C17—C16—H16A	120.4
C2—C3—H3A	120.9	C15—C16—H16A	120.5
C5—C4—C3	123.51 (8)	C16—C17—C18	117.96 (10)
C5—C4—N2	117.57 (8)	C16—C17—H17A	121.0
C3—C4—N2	118.90 (8)	C18—C17—H17A	121.0
C6—C5—C4	116.02 (8)	N5—C18—C17	123.88 (10)
C6—C5—H5A	122.0	N5—C18—H18A	118.1
C4—C5—H5A	122.0	C17—C18—H18A	118.1
C7—C6—C5	123.36 (8)	N6—C19—C20	121.90 (9)
C7—C6—N3	118.28 (8)	N6—C19—C8	116.62 (8)
C5—C6—N3	118.35 (8)	C20—C19—C8	121.44 (8)
C6—C7—C2	118.75 (8)	C21—C20—C19	118.97 (9)
C6—C7—H7A	120.6	C21—C20—H20A	120.5
C2—C7—H7A	120.6	C19—C20—H20A	120.5
N1—C8—C19	109.79 (7)	C22—C21—C20	119.36 (10)
N1—C8—C9	106.41 (7)	C22—C21—H21A	120.3
C19—C8—C9	110.08 (8)	C20—C21—H21A	120.3
N1—C8—C14	108.81 (7)	C21—C22—C23	117.80 (9)
C19—C8—C14	115.50 (8)	C21—C22—H22A	121.1
C9—C8—C14	105.82 (7)	C23—C22—H22A	121.1
N4—C9—C10	122.83 (9)	N6—C23—C22	123.72 (10)
N4—C9—C8	116.87 (8)	N6—C23—H23A	118.1
C10—C9—C8	120.26 (8)	C22—C23—H23A	118.1
C8—N1—C1—O1	5.21 (15)	C14—C8—C9—C10	−67.74 (11)
C8—N1—C1—C2	−175.97 (8)	N4—C9—C10—C11	0.72 (15)
O1—C1—C2—C3	173.68 (9)	C8—C9—C10—C11	178.49 (9)
N1—C1—C2—C3	−5.20 (13)	C9—C10—C11—C12	−0.96 (16)
O1—C1—C2—C7	−6.32 (13)	C10—C11—C12—C13	0.53 (16)
N1—C1—C2—C7	174.81 (8)	C9—N4—C13—C12	−0.44 (14)
C7—C2—C3—C4	−3.42 (13)	C11—C12—C13—N4	0.19 (15)
C1—C2—C3—C4	176.58 (8)	C18—N5—C14—C15	1.19 (14)
C2—C3—C4—C5	0.17 (14)	C18—N5—C14—C8	179.32 (8)
C2—C3—C4—N2	178.72 (8)	N1—C8—C14—N5	41.43 (10)
O2—N2—C4—C5	174.58 (8)	C19—C8—C14—N5	165.39 (8)
O3—N2—C4—C5	−4.67 (12)	C9—C8—C14—N5	−72.57 (9)
O2—N2—C4—C3	−4.06 (13)	N1—C8—C14—C15	−140.49 (9)
O3—N2—C4—C3	176.70 (8)	C19—C8—C14—C15	−16.52 (13)
C3—C4—C5—C6	2.56 (14)	C9—C8—C14—C15	105.51 (10)
N2—C4—C5—C6	−176.01 (8)	N5—C14—C15—C16	−1.18 (15)
C4—C5—C6—C7	−2.16 (14)	C8—C14—C15—C16	−179.09 (9)
C4—C5—C6—N3	178.22 (8)	C14—C15—C16—C17	0.59 (16)
O5—N3—C6—C7	29.26 (13)	C15—C16—C17—C18	−0.09 (16)
O4—N3—C6—C7	−150.69 (9)	C14—N5—C18—C17	−0.66 (15)
O5—N3—C6—C5	−151.10 (9)	C16—C17—C18—N5	0.12 (16)
O4—N3—C6—C5	28.96 (12)	C23—N6—C19—C20	1.46 (16)
C5—C6—C7—C2	−0.95 (14)	C23—N6—C19—C8	179.27 (10)
N3—C6—C7—C2	178.68 (8)	N1—C8—C19—N6	177.27 (8)
C3—C2—C7—C6	3.80 (13)	C9—C8—C19—N6	−65.91 (11)
C1—C2—C7—C6	−176.20 (8)	C14—C8—C19—N6	53.81 (12)
C1—N1—C8—C19	−70.57 (11)	N1—C8—C19—C20	−4.91 (12)
C1—N1—C8—C9	170.33 (8)	C9—C8—C19—C20	111.91 (10)
C1—N1—C8—C14	56.72 (11)	C14—C8—C19—C20	−128.36 (9)
C13—N4—C9—C10	−0.02 (14)	N6—C19—C20—C21	−2.46 (15)
C13—N4—C9—C8	−177.86 (8)	C8—C19—C20—C21	179.83 (9)
N1—C8—C9—N4	−5.49 (11)	C19—C20—C21—C22	1.36 (15)
C19—C8—C9—N4	−124.40 (9)	C20—C21—C22—C23	0.58 (16)
C14—C8—C9—N4	110.16 (9)	C19—N6—C23—C22	0.65 (18)
N1—C8—C9—C10	176.62 (9)	C21—C22—C23—N6	−1.66 (18)
C19—C8—C9—C10	57.71 (11)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···N4	0.88	2.07	2.574 (1)	115
C16—H16A···O1^i	0.95	2.34	3.2796 (13)	169
C18—H18A···O4^ii	0.95	2.52	3.4414 (13)	164
C23—H23A···O3^iii	0.95	2.58	3.2522 (15)	128

Symmetry codes: (i) −x, −y+1, −z; (ii) −x−1/2, y+1/2, −z+1/2; (iii) x+1/2, −y+3/2, z−1/2.