4-[4-(1H-Tetra-zol-5-yl)phen-oxy]benzaldehyde.

The asymmetric unit of the title compound, C(14)H(10)N(4)O(2), contains two independent mol-ecules with similar structures. In one mol-ecule, the tetra-zole ring is oriented at dihedral angles of 17.71 (16) and 57.13 (17)°, respectively, to the central benzene ring and the terminal benzene ring; in the other mol-ecule, the corresponding dihedral angles are 16.46 (18) and 75.87 (18)°. Inter-molecular N-H⋯N hydrogen bonds and weak C-H⋯O and C-H⋯N hydrogen bonds occur in the crystal structure.

Related literature

For the synthesis of 5-substituted 1H-tetra­zoles, see: Ostrovskii et al. (2008 ▶); Saikia & Phukan (2009 ▶); Nasrollahzadeh et al. (2009 ▶); Teimouri & Najafi Chermahini (2011 ▶). For related structures, see: Li et al. (2008 ▶); Hu et al. (2009 ▶); Xu et al. (2010 ▶); Deng et al. (2010 ▶).

Experimental

Crystal data

C14H10N4O2

M = 266.26

Triclinic,

a = 9.854 (4) Å

b = 9.948 (4) Å

c = 14.139 (6) Å

α = 98.537 (4)°

β = 106.668 (4)°

γ = 99.737 (4)°

V = 1279.8 (9) Å3

Z = 4

Mo Kα radiation

μ = 0.10 mm−1

T = 296 K

0.23 × 0.21 × 0.19 mm

Data collection

Bruker APEXII CCD diffractometer

9274 measured reflections

4683 independent reflections

2623 reflections with I > 2σ(I)

R int = 0.035

Refinement

R[F 2 > 2σ(F 2)] = 0.056

wR(F 2) = 0.142

S = 1.01

4683 reflections

369 parameters

30 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.41 e Å−3

Δρmin = −0.30 e Å−3

Data collection: APEX2 (Bruker, 2005 ▶); cell refinement: SAINT (Bruker, 2001 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablock(s) global, I, New_Global_Publ_Block. DOI: 10.1107/S1600536811044254/xu5357sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811044254/xu5357Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811044254/xu5357Isup3.cdx

Supplementary material file. DOI: 10.1107/S1600536811044254/xu5357Isup4.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C14H10N4O2	Z = 4
Mr = 266.26	F(000) = 552
Triclinic, P1	Dx = 1.382 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 9.854 (4) Å	Cell parameters from 1475 reflections
b = 9.948 (4) Å	θ = 2.2–21.0°
c = 14.139 (6) Å	µ = 0.10 mm−1
α = 98.537 (4)°	T = 296 K
β = 106.668 (4)°	Block, colourless
γ = 99.737 (4)°	0.23 × 0.21 × 0.19 mm
V = 1279.8 (9) Å3

Bruker APEXII CCD diffractometer	2623 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.035
graphite	θmax = 25.5°, θmin = 2.2°
φ and ω scans	h = −11→11
9274 measured reflections	k = −10→12
4683 independent reflections	l = −17→17

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)] = 0.056	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.142	H atoms treated by a mixture of independent and constrained refinement
S = 1.01	w = 1/[σ2(Fo2) + (0.0462P)2 + 0.4163P] where P = (Fo2 + 2Fc2)/3
4683 reflections	(Δ/σ)max < 0.001
369 parameters	Δρmax = 0.41 e Å−3
30 restraints	Δρmin = −0.30 e Å−3

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.

	x	y	z	Uiso*/Ueq
C1	0.8863 (3)	0.1795 (3)	1.0915 (2)	0.0414 (7)
C2	0.7457 (3)	0.1392 (3)	1.0126 (2)	0.0415 (7)
C3	0.6554 (3)	0.2318 (3)	1.0004 (2)	0.0514 (8)
H3	0.6862	0.3205	1.0416	0.062*
C4	0.5208 (3)	0.1945 (3)	0.9283 (2)	0.0602 (8)
H4	0.4598	0.2568	0.9209	0.072*
C5	0.4773 (3)	0.0638 (3)	0.8672 (2)	0.0543 (8)
C6	0.5645 (3)	−0.0298 (3)	0.8772 (2)	0.0597 (8)
H6	0.5335	−0.1177	0.8349	0.072*
C7	0.6986 (3)	0.0072 (3)	0.9504 (2)	0.0533 (8)
H7	0.7580	−0.0564	0.9583	0.064*
C8	0.3025 (3)	0.0912 (3)	0.7196 (2)	0.0558 (8)
C9	0.1567 (3)	0.0772 (4)	0.6724 (3)	0.0728 (10)
H9	0.0880	0.0209	0.6914	0.087*
C10	0.1142 (4)	0.1482 (4)	0.5964 (3)	0.0820 (11)
H10	0.0155	0.1401	0.5647	0.098*
C11	0.2142 (4)	0.2309 (4)	0.5662 (3)	0.0718 (9)
C12	0.3588 (4)	0.2389 (3)	0.6127 (2)	0.0668 (9)
H12	0.4274	0.2921	0.5918	0.080*
C13	0.4051 (3)	0.1701 (3)	0.6898 (2)	0.0629 (9)
H13	0.5037	0.1769	0.7208	0.075*
C14	0.1805 (5)	0.3200 (5)	0.4876 (3)	0.1064 (14)
H14	0.2555	0.3725	0.4720	0.128*
C15	−0.0013 (3)	0.7097 (3)	0.1508 (2)	0.0430 (7)
C16	0.1047 (3)	0.7403 (3)	0.2513 (2)	0.0455 (7)
C17	0.1222 (4)	0.6369 (3)	0.3065 (2)	0.0667 (9)
H17	0.0665	0.5468	0.2782	0.080*
C18	0.2201 (4)	0.6649 (3)	0.4020 (2)	0.0747 (11)
H18	0.2318	0.5936	0.4373	0.090*
C19	0.3005 (3)	0.7972 (3)	0.4453 (2)	0.0587 (8)
C20	0.2850 (3)	0.9026 (3)	0.3926 (2)	0.0606 (9)
H20	0.3397	0.9927	0.4219	0.073*
C21	0.1884 (3)	0.8738 (3)	0.2964 (2)	0.0530 (8)
H21	0.1788	0.9451	0.2609	0.064*
C22	0.4087 (4)	0.7458 (3)	0.6065 (2)	0.0612 (9)
C23	0.2899 (4)	0.7028 (3)	0.6363 (3)	0.0678 (9)
H23	0.2027	0.7280	0.6082	0.081*
C24	0.3016 (3)	0.6222 (3)	0.7079 (3)	0.0627 (9)
H24	0.2217	0.5927	0.7282	0.075*
C25	0.4307 (3)	0.5845 (3)	0.7501 (2)	0.0551 (8)
C26	0.5488 (4)	0.6304 (3)	0.7202 (3)	0.0644 (9)
H26	0.6365	0.6065	0.7489	0.077*
C27	0.5387 (4)	0.7110 (3)	0.6487 (3)	0.0663 (9)
H27	0.6189	0.7416	0.6290	0.080*
C28	0.4455 (4)	0.4991 (3)	0.8268 (3)	0.0734 (10)
H28	0.5360	0.4795	0.8538	0.088*
N1	0.9674 (3)	0.0935 (3)	1.12958 (18)	0.0499 (6)
N2	1.0895 (3)	0.1684 (2)	1.20221 (19)	0.0581 (7)
N3	1.0818 (3)	0.2977 (2)	1.20764 (19)	0.0584 (7)
N4	0.9565 (2)	0.3084 (2)	1.13952 (18)	0.0503 (6)
N5	−0.0625 (3)	0.5829 (2)	0.09329 (18)	0.0466 (6)
N6	−0.1563 (3)	0.5921 (2)	0.00568 (18)	0.0545 (6)
N7	−0.1514 (3)	0.7233 (2)	0.00983 (18)	0.0565 (7)
N8	−0.0556 (3)	0.7999 (2)	0.09919 (18)	0.0520 (6)
O1	0.3385 (2)	0.0200 (2)	0.79639 (17)	0.0707 (7)
O2	0.0601 (4)	0.3220 (4)	0.4469 (3)	0.1609 (14)
O3	0.4057 (2)	0.8339 (2)	0.53920 (17)	0.0789 (7)
O4	0.3497 (3)	0.4526 (3)	0.8575 (2)	0.0967 (9)
H2N	−0.053 (3)	0.499 (3)	0.107 (2)	0.058 (9)*
H1N	0.954 (3)	−0.001 (3)	1.117 (2)	0.081 (11)*

	U11	U22	U33	U12	U13	U23
C1	0.0474 (17)	0.0281 (14)	0.0483 (17)	0.0103 (13)	0.0123 (14)	0.0106 (13)
C2	0.0441 (16)	0.0303 (14)	0.0494 (17)	0.0101 (12)	0.0107 (14)	0.0121 (12)
C3	0.0529 (19)	0.0350 (15)	0.0599 (19)	0.0138 (14)	0.0082 (16)	0.0058 (14)
C4	0.0524 (19)	0.0473 (18)	0.076 (2)	0.0198 (16)	0.0077 (17)	0.0148 (17)
C5	0.0447 (18)	0.0490 (18)	0.0581 (19)	0.0046 (15)	0.0008 (15)	0.0153 (15)
C6	0.065 (2)	0.0373 (16)	0.061 (2)	0.0086 (15)	0.0021 (17)	0.0003 (14)
C7	0.0558 (19)	0.0388 (16)	0.0597 (19)	0.0161 (14)	0.0080 (16)	0.0082 (14)
C8	0.053 (2)	0.0499 (18)	0.0533 (19)	0.0130 (16)	0.0014 (16)	0.0058 (15)
C9	0.046 (2)	0.094 (3)	0.073 (2)	0.0132 (19)	0.0095 (18)	0.024 (2)
C10	0.052 (2)	0.119 (3)	0.070 (2)	0.031 (2)	0.004 (2)	0.022 (2)
C11	0.069 (2)	0.093 (3)	0.060 (2)	0.041 (2)	0.0175 (19)	0.0136 (18)
C12	0.071 (2)	0.069 (2)	0.061 (2)	0.0207 (19)	0.0215 (19)	0.0127 (18)
C13	0.0494 (19)	0.068 (2)	0.063 (2)	0.0149 (17)	0.0072 (17)	0.0101 (18)
C14	0.090 (3)	0.133 (3)	0.086 (3)	0.070 (2)	−0.007 (2)	0.011 (2)
C15	0.0487 (17)	0.0287 (14)	0.0513 (17)	0.0090 (13)	0.0157 (14)	0.0082 (13)
C16	0.0487 (17)	0.0318 (15)	0.0509 (17)	0.0096 (13)	0.0088 (14)	0.0062 (13)
C17	0.083 (2)	0.0308 (16)	0.062 (2)	−0.0002 (16)	−0.0051 (18)	0.0075 (15)
C18	0.096 (3)	0.0411 (18)	0.062 (2)	0.0041 (18)	−0.009 (2)	0.0154 (16)
C19	0.058 (2)	0.0500 (19)	0.0533 (19)	0.0019 (16)	0.0007 (16)	0.0103 (16)
C20	0.0534 (19)	0.0372 (17)	0.073 (2)	−0.0035 (14)	0.0022 (17)	0.0066 (16)
C21	0.0505 (18)	0.0336 (15)	0.067 (2)	0.0050 (14)	0.0064 (16)	0.0148 (14)
C22	0.059 (2)	0.0532 (19)	0.0505 (19)	−0.0055 (17)	−0.0011 (17)	0.0063 (16)
C23	0.053 (2)	0.065 (2)	0.071 (2)	0.0110 (17)	0.0019 (18)	0.0117 (19)
C24	0.053 (2)	0.061 (2)	0.071 (2)	0.0094 (17)	0.0178 (17)	0.0098 (18)
C25	0.058 (2)	0.0457 (18)	0.0545 (19)	0.0123 (16)	0.0111 (17)	0.0031 (15)
C26	0.053 (2)	0.062 (2)	0.070 (2)	0.0134 (17)	0.0078 (18)	0.0096 (18)
C27	0.051 (2)	0.072 (2)	0.068 (2)	0.0037 (17)	0.0157 (18)	0.0101 (19)
C28	0.085 (3)	0.060 (2)	0.080 (3)	0.026 (2)	0.030 (2)	0.011 (2)
N1	0.0518 (16)	0.0326 (14)	0.0574 (16)	0.0109 (12)	0.0044 (13)	0.0101 (12)
N2	0.0553 (16)	0.0395 (14)	0.0648 (17)	0.0116 (12)	−0.0032 (13)	0.0093 (12)
N3	0.0588 (17)	0.0371 (14)	0.0655 (17)	0.0109 (12)	−0.0001 (14)	0.0086 (12)
N4	0.0510 (15)	0.0313 (13)	0.0593 (15)	0.0086 (11)	0.0048 (13)	0.0077 (11)
N5	0.0557 (15)	0.0295 (13)	0.0505 (15)	0.0124 (12)	0.0078 (12)	0.0106 (11)
N6	0.0652 (17)	0.0411 (14)	0.0505 (16)	0.0131 (12)	0.0072 (13)	0.0103 (12)
N7	0.0693 (17)	0.0396 (14)	0.0541 (16)	0.0144 (13)	0.0083 (14)	0.0107 (12)
N8	0.0654 (16)	0.0334 (13)	0.0548 (15)	0.0156 (12)	0.0108 (13)	0.0132 (12)
O1	0.0513 (13)	0.0620 (14)	0.0781 (16)	−0.0014 (11)	−0.0063 (12)	0.0215 (12)
O2	0.142 (3)	0.222 (4)	0.138 (3)	0.066 (3)	0.038 (3)	0.081 (3)
O3	0.0761 (16)	0.0672 (15)	0.0615 (15)	−0.0176 (12)	−0.0099 (13)	0.0190 (12)
O4	0.129 (2)	0.0865 (19)	0.111 (2)	0.0483 (18)	0.071 (2)	0.0389 (17)

C1—N4	1.325 (3)	C16—C21	1.388 (4)
C1—N1	1.335 (3)	C17—C18	1.373 (4)
C1—C2	1.455 (4)	C17—H17	0.9300
C2—C3	1.381 (3)	C18—C19	1.366 (4)
C2—C7	1.389 (4)	C18—H18	0.9300
C3—C4	1.372 (4)	C19—C20	1.378 (4)
C3—H3	0.9300	C19—O3	1.381 (3)
C4—C5	1.373 (4)	C20—C21	1.374 (4)
C4—H4	0.9300	C20—H20	0.9300
C5—C6	1.366 (4)	C21—H21	0.9300
C5—O1	1.396 (3)	C22—C27	1.375 (4)
C6—C7	1.374 (4)	C22—C23	1.378 (4)
C6—H6	0.9300	C22—O3	1.384 (4)
C7—H7	0.9300	C23—C24	1.374 (4)
C8—C13	1.375 (4)	C23—H23	0.9300
C8—C9	1.372 (4)	C24—C25	1.381 (4)
C8—O1	1.378 (3)	C24—H24	0.9300
C9—C10	1.377 (4)	C25—C26	1.378 (4)
C9—H9	0.9300	C25—C28	1.464 (4)
C10—C11	1.380 (5)	C26—C27	1.373 (4)
C10—H10	0.9300	C26—H26	0.9300
C11—C12	1.369 (4)	C27—H27	0.9300
C11—C14	1.520 (5)	C28—O4	1.200 (4)
C12—C13	1.381 (4)	C28—H28	0.9300
C12—H12	0.9300	N1—N2	1.349 (3)
C13—H13	0.9300	N1—H1N	0.91 (3)
C14—O2	1.166 (4)	N2—N3	1.294 (3)
C14—H14	0.9300	N3—N4	1.363 (3)
C15—N8	1.325 (3)	N5—N6	1.343 (3)
C15—N5	1.332 (3)	N5—H2N	0.90 (3)
C15—C16	1.455 (4)	N6—N7	1.291 (3)
C16—C17	1.385 (4)	N7—N8	1.362 (3)
N4—C1—N1	107.5 (2)	C18—C17—H17	119.4
N4—C1—C2	126.2 (2)	C16—C17—H17	119.4
N1—C1—C2	126.3 (2)	C19—C18—C17	120.1 (3)
C3—C2—C7	119.0 (3)	C19—C18—H18	119.9
C3—C2—C1	119.8 (2)	C17—C18—H18	119.9
C7—C2—C1	121.1 (2)	C18—C19—C20	120.1 (3)
C4—C3—C2	120.8 (3)	C18—C19—O3	124.1 (3)
C4—C3—H3	119.6	C20—C19—O3	115.7 (3)
C2—C3—H3	119.6	C21—C20—C19	119.7 (3)
C5—C4—C3	119.0 (3)	C21—C20—H20	120.1
C5—C4—H4	120.5	C19—C20—H20	120.1
C3—C4—H4	120.5	C20—C21—C16	121.2 (3)
C6—C5—C4	121.5 (3)	C20—C21—H21	119.4
C6—C5—O1	117.8 (3)	C16—C21—H21	119.4
C4—C5—O1	120.6 (3)	C27—C22—C23	120.9 (3)
C5—C6—C7	119.3 (3)	C27—C22—O3	117.3 (3)
C5—C6—H6	120.3	C23—C22—O3	121.6 (3)
C7—C6—H6	120.3	C24—C23—C22	119.3 (3)
C6—C7—C2	120.3 (3)	C24—C23—H23	120.4
C6—C7—H7	119.8	C22—C23—H23	120.4
C2—C7—H7	119.8	C23—C24—C25	120.7 (3)
C13—C8—C9	121.2 (3)	C23—C24—H24	119.6
C13—C8—O1	122.7 (3)	C25—C24—H24	119.6
C9—C8—O1	116.1 (3)	C24—C25—C26	119.1 (3)
C8—C9—C10	118.7 (3)	C24—C25—C28	121.5 (3)
C8—C9—H9	120.7	C26—C25—C28	119.4 (3)
C10—C9—H9	120.7	C27—C26—C25	120.9 (3)
C9—C10—C11	121.6 (3)	C27—C26—H26	119.5
C9—C10—H10	119.2	C25—C26—H26	119.5
C11—C10—H10	119.2	C26—C27—C22	119.2 (3)
C12—C11—C10	118.1 (3)	C26—C27—H27	120.4
C12—C11—C14	115.6 (4)	C22—C27—H27	120.4
C10—C11—C14	126.3 (4)	O4—C28—C25	124.9 (4)
C11—C12—C13	121.7 (3)	O4—C28—H28	117.5
C11—C12—H12	119.2	C25—C28—H28	117.5
C13—C12—H12	119.2	C1—N1—N2	109.5 (2)
C8—C13—C12	118.6 (3)	C1—N1—H1N	133 (2)
C8—C13—H13	120.7	N2—N1—H1N	117 (2)
C12—C13—H13	120.7	N3—N2—N1	106.1 (2)
O2—C14—C11	119.7 (5)	N2—N3—N4	110.5 (2)
O2—C14—H14	120.2	C1—N4—N3	106.4 (2)
C11—C14—H14	120.2	C15—N5—N6	109.9 (2)
N8—C15—N5	107.1 (2)	C15—N5—H2N	129.8 (18)
N8—C15—C16	127.5 (2)	N6—N5—H2N	120.1 (18)
N5—C15—C16	125.4 (2)	N7—N6—N5	106.0 (2)
C17—C16—C21	117.8 (3)	N6—N7—N8	110.5 (2)
C17—C16—C15	120.6 (2)	C15—N8—N7	106.5 (2)
C21—C16—C15	121.6 (3)	C8—O1—C5	118.2 (2)
C18—C17—C16	121.2 (3)	C19—O3—C22	119.9 (2)
N4—C1—C2—C3	−17.7 (4)	C19—C20—C21—C16	0.5 (5)
N1—C1—C2—C3	161.4 (3)	C17—C16—C21—C20	−0.1 (4)
N4—C1—C2—C7	163.8 (3)	C15—C16—C21—C20	178.0 (3)
N1—C1—C2—C7	−17.1 (4)	C27—C22—C23—C24	−1.0 (5)
C7—C2—C3—C4	0.3 (4)	O3—C22—C23—C24	−176.1 (3)
C1—C2—C3—C4	−178.3 (3)	C22—C23—C24—C25	0.1 (5)
C2—C3—C4—C5	−0.8 (5)	C23—C24—C25—C26	0.8 (5)
C3—C4—C5—C6	0.5 (5)	C23—C24—C25—C28	179.7 (3)
C3—C4—C5—O1	176.9 (3)	C24—C25—C26—C27	−0.8 (5)
C4—C5—C6—C7	0.3 (5)	C28—C25—C26—C27	−179.8 (3)
O1—C5—C6—C7	−176.1 (3)	C25—C26—C27—C22	−0.1 (5)
C5—C6—C7—C2	−0.9 (5)	C23—C22—C27—C26	1.0 (5)
C3—C2—C7—C6	0.6 (4)	O3—C22—C27—C26	176.3 (3)
C1—C2—C7—C6	179.1 (3)	C24—C25—C28—O4	1.9 (5)
C13—C8—C9—C10	−2.4 (5)	C26—C25—C28—O4	−179.2 (3)
O1—C8—C9—C10	178.8 (3)	N4—C1—N1—N2	0.0 (3)
C8—C9—C10—C11	0.8 (6)	C2—C1—N1—N2	−179.2 (3)
C9—C10—C11—C12	1.3 (5)	C1—N1—N2—N3	0.0 (3)
C9—C10—C11—C14	−176.4 (3)	N1—N2—N3—N4	−0.1 (3)
C10—C11—C12—C13	−1.8 (5)	N1—C1—N4—N3	−0.1 (3)
C14—C11—C12—C13	176.1 (3)	C2—C1—N4—N3	179.1 (3)
C9—C8—C13—C12	1.9 (5)	N2—N3—N4—C1	0.1 (3)
O1—C8—C13—C12	−179.4 (3)	N8—C15—N5—N6	−0.5 (3)
C11—C12—C13—C8	0.3 (5)	C16—C15—N5—N6	179.3 (3)
C12—C11—C14—O2	−177.7 (4)	C15—N5—N6—N7	0.3 (3)
C10—C11—C14—O2	0.0 (7)	N5—N6—N7—N8	−0.1 (3)
N8—C15—C16—C17	162.4 (3)	N5—C15—N8—N7	0.4 (3)
N5—C15—C16—C17	−17.4 (4)	C16—C15—N8—N7	−179.4 (3)
N8—C15—C16—C21	−15.7 (5)	N6—N7—N8—C15	−0.2 (3)
N5—C15—C16—C21	164.5 (3)	C13—C8—O1—C5	21.7 (4)
C21—C16—C17—C18	−0.8 (5)	C9—C8—O1—C5	−159.5 (3)
C15—C16—C17—C18	−178.9 (3)	C6—C5—O1—C8	−120.5 (3)
C16—C17—C18—C19	1.4 (6)	C4—C5—O1—C8	63.0 (4)
C17—C18—C19—C20	−1.0 (5)	C18—C19—O3—C22	−17.6 (5)
C17—C18—C19—O3	−177.2 (3)	C20—C19—O3—C22	166.1 (3)
C18—C19—C20—C21	0.1 (5)	C27—C22—O3—C19	128.5 (3)
O3—C19—C20—C21	176.6 (3)	C23—C22—O3—C19	−56.3 (4)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···N8i	0.91 (3)	1.94 (3)	2.849 (4)	174 (2)
N5—H2N···N4ii	0.90 (3)	2.03 (3)	2.924 (3)	176 (3)
C4—H4···O4	0.93	2.54	3.420 (4)	158
C17—H17···N3ii	0.93	2.58	3.365 (4)	143
C23—H23···O2iii	0.93	2.42	3.262 (6)	151

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯N8i	0.91 (3)	1.94 (3)	2.849 (4)	174 (2)
N5—H2N⋯N4ii	0.90 (3)	2.03 (3)	2.924 (3)	176 (3)
C4—H4⋯O4	0.93	2.54	3.420 (4)	158
C17—H17⋯N3ii	0.93	2.58	3.365 (4)	143
C23—H23⋯O2iii	0.93	2.42	3.262 (6)	151

Symmetry codes: (i) ; (ii) ; (iii) .