N-Benz­yl­oxy-1H-benzo­triazole-1-carbox­amide: a hydrogen-bonded tetra­mer based upon a rare R₄⁴(20) structural motif

The title compound, C₁₄H₁₂N₄O₂, is the first example of a heterocyclic substituted hydroxamic derivative. The asymmetric unit consists of two molecules. The molecules are linked into centrosymmetric R₄⁴(20) tetramers by four strong hydrogen bonds of the N-H...O and N-H...N types. These tetramers are connected through C-H...O interactions into a three-dimensional network.

S1. Comment

Recently, much attention has been focused on studies of the physicochemical, structural and catalytic properties of 1,3,5-trihydroxy-1,3,5-triazinane-2,4,6-trione (Jadrijević-Mladar Takač et al., 2006; Hirai et al., 2003, 2004; Caira et al., 2006). Active organooxyisocyanate derivatives have been employed as precursors in the synthesis of 1,3,5-trihydroxy-1,3,5-triazinane-2,4,6-trione. Intensive investigation of the properties of organooxyisocyanates revealed that, because of their low stability, only some compounds could serve as donors of the organooxyisocyanate group (Staab & Benz, 1961; Major & Hedrick, 1965; Berndt, 1970). Butula & Jadrijević-Mladar Takač (2000) reported that benzotriazole-1-carboxylic acid benzyloxy-amide, (I), can be used as a solid benzyloxyisocyanate donor.

Annealing of (I) to a sufficiently high temperature induces decomposition to benzotriazole [one of the most effective inhibitors of copper corrosion in neutral and alkaline conditions (Cotton & Scholes, 1967)] and benzyloxyisocyanate, a precursor for building 1,3,5-tribenzyloxy-1,3,5-triazinane-2,4,6-trione. 1,3,5-Tribenzyloxy-1,3,5-triazinane-2,4,6-trione can be easily converted to 1,3,5-trihydroxy-1,3,5-triazinane-2,4,6-trione by reduction with hydrogen. The benzyloxyaminocarbonyl group can be easily reduced to the hydroxylamine group, thus providing an alternative path for synthesis of hydroxamic acids and hydroxyureas. With this goal in mind and in an attempt to understand further the structure of hydroxamic acid and its derivatives (Matković-Čalogović et al., 2003; Đilović et al., 2006, 2007), the structure of (I) was determined using the single-crystal X-ray diffraction method.

The title compound is an example of a valuable precursor in hydroxamic acid chemistry. The asymmetric unit of (I) consists of two crystallographically independent molecules. A view of (I), including the atom-labeling scheme, is shown in Fig. 1, and selected geometric parameters are shown in Table 1. A trans configuration of the carbonyl O atoms with respect to the amide H atom is observed, and the N² atom of the 1,2,3-triazole unit is in a cis configuration with respect to the amide N atom. Compound (I) contains two terminal aromatic (and also planar) substituents (the benzotriazole and phenyl rings), which are connected to the N-methoxy formamide segment. If we exclude the benzyl group, the rest of molecule is almost planar. The planes of the two symmetrically independent molecules are almost orthogonal [82.53 (1)°]. The molecules are linked into centrosymmetric tetramers to give a very rare structural motif [R⁴₄(20); Etter et al., 1990]. This four-membered circuit is formed by molecules found at symmetry sites (x, y, z) and (-x + 1, -y + 1, -z + 1), which are linked together by four hydrogen bonds of the N—H···O and N—H···N types (Table 2 and Fig. 2). In addition, the tetramers in the crystal structure are connected through C—H···O van der Waals interactions to form a three-dimensional network (Table 1 and Fig. 3).

Related literature

For related literature, see: Berndt (1970); Butula & Jadrijević-Mladar Takač (2000); Caira et al. (2006); Cotton & Scholes (1967); Etter et al. (1990); Hirai et al. (2003, 2004); Major & Hedrick (1965); Matković-Čalogović, Bešić, Biruš & Gabričević (2003); Sheldrick (2008); Staab & Benz (1961); Đilović et al. (2006, 2007).

S2. Experimental

Benzotriazole-1-carboxylic acid benzyloxyamide was synthesized by a previously published procedure (Butula et al., 2000). The structure and purity were confirmed by means of thin-layer chromatography, FT–IR and NMR analyses. The compound was crystallized by slow evaporation from a saturated diethyl ether solution at room temperature (the beaker containing the solution was covered with aluminium foil to slow down evaporation). Colorless crystals of good quality were obtained after three weeks, and these were stable for several months when exposed to the atmosphere.

S3. Refinement

H atoms were constrained to ideal geometry using an appropriate riding model, with C—H = 0.93–0.97Å and N—H = 0.86Å, and with U_iso(H) = 1.2U_eq(C,N).

Computing details

Data collection: CrysAlis CCD (Oxford Diffraction, 2003); cell refinement: CrysAlis RED (Oxford Diffraction, 2003); data reduction: CrysAlis RED (Oxford Diffraction, 2003); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997) and Mercury (Macrae et al., 2006); software used to prepare material for publication: PLATON (Spek, 2003).

Figures

	Fig. 1. A view of the asymmetric unit of (I), with the atom-labeling scheme. Displacement ellipsoids are shown at the 30% probability level. H atoms have been omitted for clarity.
	Fig. 2. The crystal packing of (I), showing the tetramers connected by hydrogen bonding. Only one tetramer is shown.
	Fig. 3. The three-dimensional network in (I), indicating the hydrogen bonding and C—H···π interactions. Only one layer of molecules is shown.

N-benzyloxy-1H-benzotriazole-1-carboxamide

Crystal data

C14H12N4O2	Z = 8
Mr = 268.28	F(000) = 1120
Monoclinic, P21/c	Dx = 1.327 Mg m^−3
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 13.4267 (9) Å	µ = 0.09 mm^−1
b = 20.6647 (7) Å	T = 293 K
c = 11.0684 (5) Å	Prism, colorless
β = 119.020 (4)°	0.80 × 0.50 × 0.40 mm
V = 2685.5 (3) Å^3

Data collection

Oxford Diffraction Xcalibur CCD diffractometer	5236 independent reflections
Radiation source: fine-focus sealed tube	3136 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.020
ω scans	θmax = 26.0°, θmin = 3.9°
Absorption correction: analytical (CrysAlis RED; Oxford Diffraction, 2003)	h = −16→16
Tmin = 0.929, Tmax = 0.964	k = −25→24
17530 measured reflections	l = −13→13

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)] = 0.043	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.138	H-atom parameters constrained
S = 1.05	w = 1/[σ^2(Fo^2) + (0.0729P)^2 + 0.0868P] where P = (Fo^2 + 2Fc^2)/3
5236 reflections	(Δ/σ)max < 0.001
361 parameters	Δρmax = 0.15 e Å^−3
0 restraints	Δρmin = −0.17 e Å^−3

Special details

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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.

The non-hydrogen atomic positions were determined by direct methods with SHELXS (Sheldrick, 1990) and refined to convergence by the full-matrix least-squares method with anisotropic thermal parameters using SHELXL97 (Sheldrick, 1997). At this stage the positions of all hydrogen atoms were obtained from the difference Fourier map. However, the number of observed reflections did not justify the refinement of hydrogen atoms with isotropic thermal parameters so they were determined on stereochemical grounds, each riding on their carrier atom.

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

	x	y	z	Uiso*/Ueq
C11	−0.05750 (15)	0.54847 (9)	0.15734 (18)	0.0619 (5)
C12	−0.0921 (2)	0.60431 (11)	−0.1177 (2)	0.0994 (8)
H12A	−0.1641	0.5935	−0.1980	0.119*
H12B	−0.0452	0.5657	−0.0875	0.119*
C13	−0.03353 (19)	0.65620 (9)	−0.1519 (2)	0.0737 (5)
C14	−0.0899 (2)	0.69158 (11)	−0.2692 (2)	0.0924 (7)
H14	−0.1665	0.6832	−0.3286	0.111*
C15	−0.0364 (4)	0.73939 (14)	−0.3021 (3)	0.1243 (11)
H15	−0.0769	0.7626	−0.3837	0.149*
C16	0.0713 (5)	0.75271 (17)	−0.2195 (5)	0.1420 (14)
H16	0.1062	0.7859	−0.2420	0.170*
C17	0.1324 (3)	0.71840 (19)	−0.1013 (5)	0.1383 (12)
H17	0.2092	0.7274	−0.0439	0.166*
C18	0.0791 (2)	0.66963 (13)	−0.0668 (3)	0.1064 (8)
H18	0.1201	0.6462	0.0143	0.128*
C19	−0.11694 (14)	0.42756 (9)	0.34449 (19)	0.0632 (5)
C110	−0.08703 (18)	0.38276 (9)	0.4499 (2)	0.0758 (5)
H110	−0.1416	0.3591	0.4596	0.091*
C111	0.02665 (19)	0.37525 (10)	0.5389 (2)	0.0811 (6)
H111	0.0501	0.3457	0.6110	0.097*
C112	0.10800 (17)	0.41061 (10)	0.5243 (2)	0.0763 (6)
H112	0.1845	0.4038	0.5872	0.092*
C113	0.08058 (14)	0.45503 (9)	0.42133 (19)	0.0657 (5)
H113	0.1357	0.4788	0.4128	0.079*
C114	−0.03495 (14)	0.46238 (8)	0.33038 (17)	0.0575 (4)
N11	−0.14141 (13)	0.57951 (8)	0.05157 (16)	0.0802 (5)
H11	−0.2116	0.5694	0.0219	0.096*
N12	−0.09740 (11)	0.50097 (7)	0.21676 (14)	0.0614 (4)
N13	−0.21174 (11)	0.49021 (8)	0.16611 (16)	0.0729 (4)
N14	−0.22329 (12)	0.44640 (8)	0.24205 (17)	0.0732 (4)
O11	0.04309 (10)	0.55717 (6)	0.20421 (14)	0.0811 (4)
O12	−0.11077 (11)	0.62878 (6)	−0.00859 (13)	0.0750 (4)
C21	−0.53559 (14)	0.45700 (8)	0.20891 (16)	0.0558 (4)
C22	−0.51440 (18)	0.40227 (9)	−0.03991 (18)	0.0744 (5)
H22A	−0.4484	0.4236	−0.0358	0.089*
H22B	−0.5763	0.4333	−0.0725	0.089*
C23	−0.54794 (17)	0.34586 (8)	−0.13544 (19)	0.0632 (5)
C24	−0.65719 (18)	0.32140 (10)	−0.1935 (2)	0.0766 (6)
H24	−0.7092	0.3395	−0.1704	0.092*
C25	−0.6900 (2)	0.27063 (11)	−0.2849 (2)	0.0934 (7)
H25	−0.7642	0.2551	−0.3238	0.112*
C26	−0.6165 (3)	0.24325 (12)	−0.3188 (3)	0.1029 (8)
H26	−0.6401	0.2089	−0.3807	0.123*
C27	−0.5077 (3)	0.26523 (12)	−0.2634 (3)	0.1017 (8)
H27	−0.4569	0.2460	−0.2870	0.122*
C28	−0.4728 (2)	0.31721 (11)	−0.1703 (2)	0.0853 (6)
H28	−0.3984	0.3324	−0.1318	0.102*
C29	−0.46956 (14)	0.58683 (8)	0.44864 (17)	0.0586 (4)
C210	−0.49630 (17)	0.63497 (9)	0.5149 (2)	0.0730 (5)
H210	−0.4402	0.6610	0.5818	0.088*
C211	−0.60840 (18)	0.64265 (10)	0.4779 (2)	0.0830 (6)
H211	−0.6292	0.6745	0.5208	0.100*
C212	−0.69266 (17)	0.60355 (10)	0.3766 (2)	0.0833 (6)
H212	−0.7683	0.6103	0.3537	0.100*
C213	−0.66768 (14)	0.55586 (9)	0.3100 (2)	0.0690 (5)
H213	−0.7242	0.5301	0.2427	0.083*
C214	−0.55337 (13)	0.54781 (8)	0.34827 (16)	0.0557 (4)
N21	−0.45613 (13)	0.43003 (7)	0.18702 (15)	0.0686 (4)
H21	−0.3871	0.4439	0.2285	0.082*
N22	−0.49401 (10)	0.50768 (7)	0.30783 (13)	0.0564 (4)
N23	−0.37900 (11)	0.52190 (8)	0.38059 (16)	0.0682 (4)
N24	−0.36489 (12)	0.56878 (8)	0.46365 (16)	0.0706 (4)
O21	−0.63545 (10)	0.44262 (6)	0.15447 (13)	0.0728 (4)
O22	−0.48790 (10)	0.37882 (6)	0.09524 (11)	0.0659 (3)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C11	0.0510 (10)	0.0733 (13)	0.0594 (11)	−0.0063 (8)	0.0252 (9)	−0.0040 (9)
C12	0.146 (2)	0.0805 (16)	0.0901 (16)	−0.0269 (14)	0.0718 (16)	−0.0189 (13)
C13	0.0923 (15)	0.0643 (13)	0.0715 (14)	−0.0054 (10)	0.0452 (12)	−0.0104 (10)
C14	0.1135 (18)	0.0827 (16)	0.0788 (16)	−0.0013 (13)	0.0450 (14)	−0.0066 (13)
C15	0.208 (4)	0.082 (2)	0.100 (2)	−0.013 (2)	0.088 (3)	0.0037 (15)
C16	0.212 (4)	0.105 (3)	0.166 (4)	−0.063 (3)	0.137 (4)	−0.042 (3)
C17	0.108 (2)	0.148 (3)	0.165 (3)	−0.042 (2)	0.071 (2)	−0.045 (3)
C18	0.1058 (19)	0.0939 (18)	0.1041 (19)	−0.0010 (15)	0.0389 (16)	−0.0033 (14)
C19	0.0548 (10)	0.0685 (12)	0.0677 (12)	0.0002 (8)	0.0309 (9)	−0.0057 (9)
C110	0.0817 (14)	0.0694 (13)	0.0889 (14)	−0.0035 (10)	0.0513 (12)	0.0003 (11)
C111	0.0879 (15)	0.0768 (14)	0.0812 (14)	0.0158 (11)	0.0430 (13)	0.0140 (11)
C112	0.0662 (12)	0.0808 (14)	0.0762 (14)	0.0101 (10)	0.0301 (10)	0.0029 (11)
C113	0.0523 (10)	0.0743 (12)	0.0672 (12)	0.0027 (8)	0.0264 (9)	−0.0022 (10)
C114	0.0533 (9)	0.0625 (11)	0.0592 (11)	−0.0009 (8)	0.0294 (8)	−0.0057 (8)
N11	0.0575 (9)	0.0964 (12)	0.0730 (11)	−0.0117 (8)	0.0208 (8)	0.0192 (9)
N12	0.0419 (7)	0.0782 (10)	0.0610 (9)	−0.0033 (6)	0.0225 (7)	−0.0002 (8)
N13	0.0450 (8)	0.0929 (12)	0.0759 (10)	−0.0046 (7)	0.0256 (7)	0.0034 (9)
N14	0.0560 (9)	0.0846 (12)	0.0819 (11)	−0.0068 (8)	0.0359 (9)	0.0012 (9)
O11	0.0461 (7)	0.1024 (10)	0.0862 (9)	−0.0092 (6)	0.0253 (7)	0.0087 (8)
O12	0.0822 (9)	0.0732 (9)	0.0691 (8)	−0.0093 (7)	0.0364 (7)	−0.0007 (7)
C21	0.0519 (10)	0.0614 (11)	0.0472 (9)	−0.0060 (8)	0.0187 (8)	0.0066 (8)
C22	0.0961 (14)	0.0641 (12)	0.0613 (12)	−0.0019 (10)	0.0368 (11)	0.0068 (10)
C23	0.0777 (12)	0.0565 (11)	0.0567 (11)	0.0099 (9)	0.0336 (10)	0.0110 (9)
C24	0.0832 (14)	0.0752 (14)	0.0663 (12)	0.0098 (11)	0.0323 (11)	0.0025 (11)
C25	0.1028 (17)	0.0816 (16)	0.0763 (15)	−0.0022 (13)	0.0280 (14)	−0.0022 (12)
C26	0.155 (3)	0.0763 (16)	0.0764 (16)	0.0097 (17)	0.0551 (18)	−0.0002 (12)
C27	0.159 (3)	0.0762 (17)	0.1069 (19)	0.0390 (16)	0.094 (2)	0.0189 (14)
C28	0.0957 (15)	0.0805 (15)	0.0925 (16)	0.0175 (12)	0.0557 (13)	0.0230 (13)
C29	0.0509 (9)	0.0641 (11)	0.0519 (10)	−0.0030 (8)	0.0178 (8)	0.0040 (8)
C210	0.0736 (13)	0.0723 (12)	0.0650 (12)	−0.0100 (9)	0.0272 (10)	−0.0085 (10)
C211	0.0788 (14)	0.0771 (14)	0.0937 (16)	−0.0007 (10)	0.0424 (12)	−0.0114 (12)
C212	0.0641 (12)	0.0832 (14)	0.1028 (16)	0.0001 (10)	0.0406 (12)	−0.0061 (13)
C213	0.0521 (10)	0.0719 (13)	0.0740 (12)	−0.0067 (8)	0.0235 (9)	−0.0026 (10)
C214	0.0506 (9)	0.0596 (11)	0.0514 (10)	−0.0034 (7)	0.0205 (8)	0.0069 (8)
N21	0.0602 (9)	0.0770 (10)	0.0681 (10)	−0.0164 (7)	0.0307 (8)	−0.0181 (8)
N22	0.0437 (7)	0.0653 (9)	0.0520 (8)	−0.0079 (6)	0.0167 (6)	−0.0025 (7)
N23	0.0466 (8)	0.0811 (11)	0.0673 (10)	−0.0080 (7)	0.0201 (7)	−0.0062 (8)
N24	0.0535 (9)	0.0793 (11)	0.0660 (10)	−0.0109 (7)	0.0186 (7)	−0.0106 (8)
O21	0.0494 (7)	0.0884 (9)	0.0677 (8)	−0.0141 (6)	0.0183 (6)	−0.0087 (7)
O22	0.0792 (8)	0.0597 (8)	0.0580 (7)	−0.0090 (6)	0.0328 (6)	−0.0011 (6)

Geometric parameters (Å, º)

C11—O11	1.2024 (19)	C21—O21	1.2104 (19)
C11—N11	1.331 (2)	C21—N21	1.326 (2)
C11—N12	1.423 (2)	C21—N22	1.419 (2)
C12—O12	1.439 (2)	C22—O22	1.443 (2)
C12—C13	1.483 (3)	C22—C23	1.489 (2)
C12—H12A	0.9700	C22—H22A	0.9700
C12—H12B	0.9700	C22—H22B	0.9700
C13—C14	1.356 (3)	C23—C28	1.376 (3)
C13—C18	1.367 (3)	C23—C24	1.380 (3)
C14—C15	1.370 (4)	C24—C25	1.374 (3)
C14—H14	0.9300	C24—H24	0.9300
C15—C16	1.312 (5)	C25—C26	1.339 (4)
C15—H15	0.9300	C25—H25	0.9300
C16—C17	1.359 (5)	C26—C27	1.359 (4)
C16—H16	0.9300	C26—H26	0.9300
C17—C18	1.393 (4)	C27—C28	1.403 (3)
C17—H17	0.9300	C27—H27	0.9300
C18—H18	0.9300	C28—H28	0.9300
C19—N14	1.380 (2)	C29—C210	1.383 (2)
C19—C114	1.386 (2)	C29—N24	1.384 (2)
C19—C110	1.388 (3)	C29—C214	1.392 (2)
C110—C111	1.366 (3)	C210—C211	1.364 (3)
C110—H110	0.9300	C210—H210	0.9300
C111—C112	1.387 (3)	C211—C212	1.400 (3)
C111—H111	0.9300	C211—H211	0.9300
C112—C113	1.367 (3)	C212—C213	1.366 (3)
C112—H112	0.9300	C212—H212	0.9300
C113—C114	1.388 (2)	C213—C214	1.390 (2)
C113—H113	0.9300	C213—H213	0.9300
C114—N12	1.378 (2)	C214—N22	1.367 (2)
N11—O12	1.3839 (19)	N21—O22	1.3831 (17)
N11—H11	0.8600	N21—H21	0.8600
N12—N13	1.3732 (18)	N22—N23	1.3830 (18)
N13—N14	1.295 (2)	N23—N24	1.2847 (19)
O11—C11—N11	126.99 (18)	O21—C21—N21	126.94 (17)
O11—C11—N12	119.98 (16)	O21—C21—N22	119.43 (16)
N11—C11—N12	113.03 (15)	N21—C21—N22	113.63 (14)
O12—C12—C13	106.87 (16)	O22—C22—C23	108.10 (14)
O12—C12—H12A	110.3	O22—C22—H22A	110.1
C13—C12—H12A	110.3	C23—C22—H22A	110.1
O12—C12—H12B	110.3	O22—C22—H22B	110.1
C13—C12—H12B	110.3	C23—C22—H22B	110.1
H12A—C12—H12B	108.6	H22A—C22—H22B	108.4
C14—C13—C18	117.9 (2)	C28—C23—C24	118.0 (2)
C14—C13—C12	121.0 (2)	C28—C23—C22	121.7 (2)
C18—C13—C12	121.1 (2)	C24—C23—C22	120.27 (18)
C13—C14—C15	121.5 (3)	C25—C24—C23	120.7 (2)
C13—C14—H14	119.2	C25—C24—H24	119.6
C15—C14—H14	119.2	C23—C24—H24	119.6
C16—C15—C14	120.5 (3)	C26—C25—C24	120.8 (3)
C16—C15—H15	119.7	C26—C25—H25	119.6
C14—C15—H15	119.7	C24—C25—H25	119.6
C15—C16—C17	120.6 (3)	C25—C26—C27	120.6 (2)
C15—C16—H16	119.7	C25—C26—H26	119.7
C17—C16—H16	119.7	C27—C26—H26	119.7
C16—C17—C18	119.4 (3)	C26—C27—C28	119.3 (2)
C16—C17—H17	120.3	C26—C27—H27	120.3
C18—C17—H17	120.3	C28—C27—H27	120.3
C13—C18—C17	120.1 (3)	C23—C28—C27	120.4 (2)
C13—C18—H18	119.9	C23—C28—H28	119.8
C17—C18—H18	119.9	C27—C28—H28	119.8
N14—C19—C114	108.83 (16)	C210—C29—N24	129.80 (16)
N14—C19—C110	129.87 (18)	C210—C29—C214	121.51 (16)
C114—C19—C110	121.30 (17)	N24—C29—C214	108.68 (15)
C111—C110—C19	116.63 (19)	C211—C210—C29	117.20 (18)
C111—C110—H110	121.7	C211—C210—H210	121.4
C19—C110—H110	121.7	C29—C210—H210	121.4
C110—C111—C112	121.6 (2)	C210—C211—C212	121.2 (2)
C110—C111—H111	119.2	C210—C211—H211	119.4
C112—C111—H111	119.2	C212—C211—H211	119.4
C113—C112—C111	122.81 (19)	C213—C212—C211	122.28 (19)
C113—C112—H112	118.6	C213—C212—H212	118.9
C111—C112—H112	118.6	C211—C212—H212	118.9
C112—C113—C114	115.60 (17)	C212—C213—C214	116.48 (17)
C112—C113—H113	122.2	C212—C213—H213	121.8
C114—C113—H113	122.2	C214—C213—H213	121.8
N12—C114—C19	103.79 (14)	N22—C214—C213	134.90 (16)
N12—C114—C113	134.14 (16)	N22—C214—C29	103.81 (14)
C19—C114—C113	122.05 (17)	C213—C214—C29	121.29 (17)
C11—N11—O12	117.09 (15)	C21—N21—O22	117.84 (14)
C11—N11—H11	121.5	C21—N21—H21	121.1
O12—N11—H11	121.5	O22—N21—H21	121.1
N13—N12—C114	110.11 (14)	C214—N22—N23	110.12 (13)
N13—N12—C11	121.33 (14)	C214—N22—C21	128.79 (13)
C114—N12—C11	128.49 (14)	N23—N22—C21	121.08 (14)
N14—N13—N12	108.08 (14)	N24—N23—N22	108.20 (14)
N13—N14—C19	109.18 (14)	N23—N24—C29	109.19 (13)
N11—O12—C12	111.04 (14)	N21—O22—C22	109.73 (12)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N11—H11···O21^i	0.86	2.05	2.785 (2)	143
N21—H21···N14	0.86	2.13	2.900 (3)	149
C15—H15···O12^ii	0.93	2.56	3.380 (5)	148
C212—H212···O11^iii	0.93	2.51	3.252 (6)	137

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