1-[1-(4-Nitro­phen­yl)-1H-tetra­zol-5-yl]-1H-1,2,3-benzotriazole

In the title compound, C₁₃H₈N₈O₂, the benzotriazole group forms a dihedral angle of 17.56 (12)° with the tetra­zole ring and conjugation exists between them. The nitro­benzene group lies perpendicular to the tetra­zole ring and there is no conjugation.

Key indicators

• Single-crystal X-ray study
• T = 292 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.051
• wR factor = 0.170
• Data-to-parameter ratio = 13.0

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT230_ALERT_2_C Hirshfeld Test Diff for    N12    -   C9      ..       5.70 su

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   1 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
   1 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
   0 ALERT type 5 Informative message, check

---

Computing details

Data collection: R3m Software (Nicolet, 1980); cell refinement: R3m Software; data reduction: R3m Software; program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 2003); software used to prepare material for publication: SHELXL97 and PLATON.

1-[1-(4-Nitrophenyl)-1H-tetrazol-5-yl]-1H-1,2,3-benzotriazole

Crystal data

C13H8N8O2	F(000) = 632
Mr = 308.27	Dx = 1.526 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 25 reflections
a = 5.0841 (17) Å	θ = 11.7–18.1°
b = 14.024 (4) Å	µ = 0.11 mm^−1
c = 18.836 (6) Å	T = 292 K
β = 92.14 (3)°	Prism, colourless
V = 1342.1 (7) Å^3	0.36 × 0.24 × 0.16 mm
Z = 4

Data collection

Nicolet R3m diffractometer	Rint = 0.068
Radiation source: fine-focus sealed tube	θmax = 27.6°, θmin = 1.8°
Graphite monochromator	h = 0→6
ω/2θ scans	k = 0→18
3457 measured reflections	l = −24→24
3113 independent reflections	3 standard reflections every 100 reflections
1933 reflections with I > 2σ(I)	intensity decay: none

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)] = 0.051	Hydrogen site location: difference Fourier map
wR(F^2) = 0.170	All H-atom parameters refined
S = 1.05	w = 1/[σ^2(Fo^2) + (0.0992P)^2 + 0.0401P] where P = (Fo^2 + 2Fc^2)/3
3113 reflections	(Δ/σ)max < 0.001
240 parameters	Δρmax = 0.17 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
N1	0.6158 (3)	0.31499 (11)	0.29397 (8)	0.0471 (4)
N2	0.4191 (4)	0.31325 (13)	0.24291 (9)	0.0604 (5)
N3	0.3741 (4)	0.40077 (14)	0.22523 (10)	0.0653 (5)
N4	0.5351 (4)	0.46136 (12)	0.26266 (9)	0.0576 (5)
C5	0.6809 (4)	0.40678 (13)	0.30419 (10)	0.0452 (4)
C6	0.7030 (4)	0.22744 (13)	0.32688 (10)	0.0452 (4)
C7	0.5776 (4)	0.19458 (15)	0.38561 (11)	0.0550 (5)
H7	0.434 (5)	0.2338 (19)	0.4074 (13)	0.073 (7)*
C8	0.6546 (5)	0.10808 (16)	0.41490 (12)	0.0570 (5)
H8	0.566 (5)	0.0798 (17)	0.4542 (13)	0.069 (7)*
C9	0.8540 (4)	0.05880 (13)	0.38430 (10)	0.0484 (5)
C10	0.9809 (5)	0.09145 (16)	0.32622 (12)	0.0574 (5)
H10	1.118 (5)	0.0559 (18)	0.3070 (14)	0.073 (7)*
C11	0.9015 (5)	0.17740 (15)	0.29685 (12)	0.0563 (5)
H11	0.976 (5)	0.2008 (18)	0.2562 (15)	0.079 (8)*
N12	0.9347 (4)	−0.03395 (13)	0.41478 (10)	0.0605 (5)
O1	0.7978 (4)	−0.06972 (12)	0.45968 (9)	0.0768 (5)
O2	1.1346 (4)	−0.07028 (13)	0.39405 (12)	0.0840 (6)
N13	0.8742 (3)	0.44022 (11)	0.35164 (8)	0.0466 (4)
N14	1.0711 (3)	0.38140 (12)	0.37885 (10)	0.0548 (4)
N15	1.2266 (3)	0.43208 (13)	0.41887 (10)	0.0575 (5)
C16	1.1376 (4)	0.52520 (14)	0.41924 (10)	0.0492 (5)
C17	0.9123 (4)	0.53254 (13)	0.37556 (10)	0.0452 (4)
C18	0.7788 (5)	0.61738 (15)	0.36410 (12)	0.0553 (5)
H18	0.625 (5)	0.6206 (17)	0.3331 (12)	0.065 (7)*
C19	0.8827 (5)	0.69506 (16)	0.39936 (13)	0.0620 (6)
H19	0.797 (5)	0.754 (2)	0.3943 (13)	0.073 (7)*
C20	1.1087 (5)	0.68945 (17)	0.44400 (13)	0.0647 (6)
H20	1.172 (5)	0.742 (2)	0.4681 (14)	0.077 (8)*
C21	1.2392 (5)	0.60524 (16)	0.45541 (12)	0.0597 (6)
H21	1.383 (5)	0.6018 (17)	0.4837 (12)	0.060 (7)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N1	0.0530 (9)	0.0381 (8)	0.0496 (8)	−0.0018 (7)	−0.0069 (7)	0.0007 (7)
N2	0.0684 (12)	0.0503 (10)	0.0609 (10)	−0.0077 (9)	−0.0200 (9)	0.0032 (8)
N3	0.0760 (13)	0.0515 (10)	0.0664 (11)	−0.0057 (9)	−0.0251 (10)	0.0106 (8)
N4	0.0673 (11)	0.0437 (9)	0.0605 (10)	−0.0041 (8)	−0.0160 (9)	0.0077 (7)
C5	0.0501 (10)	0.0364 (9)	0.0488 (9)	−0.0028 (8)	−0.0014 (8)	0.0028 (8)
C6	0.0512 (10)	0.0345 (9)	0.0494 (10)	−0.0028 (8)	−0.0058 (8)	−0.0006 (7)
C7	0.0607 (13)	0.0490 (11)	0.0558 (11)	0.0066 (10)	0.0067 (10)	0.0031 (9)
C8	0.0667 (13)	0.0504 (12)	0.0543 (11)	0.0037 (10)	0.0053 (10)	0.0097 (9)
C9	0.0581 (11)	0.0327 (9)	0.0533 (10)	−0.0021 (8)	−0.0119 (9)	−0.0011 (8)
C10	0.0624 (13)	0.0420 (10)	0.0681 (13)	0.0066 (9)	0.0070 (11)	−0.0052 (9)
C11	0.0654 (13)	0.0434 (11)	0.0608 (12)	−0.0015 (9)	0.0124 (11)	0.0011 (9)
N12	0.0743 (13)	0.0417 (9)	0.0642 (11)	−0.0011 (9)	−0.0150 (10)	−0.0010 (8)
O1	0.1083 (14)	0.0493 (9)	0.0725 (10)	−0.0007 (9)	−0.0011 (10)	0.0148 (8)
O2	0.0815 (12)	0.0572 (11)	0.1127 (15)	0.0218 (9)	−0.0034 (11)	0.0102 (10)
N13	0.0493 (9)	0.0353 (8)	0.0546 (9)	−0.0013 (6)	−0.0067 (7)	−0.0009 (7)
N14	0.0547 (10)	0.0451 (9)	0.0636 (10)	0.0046 (7)	−0.0083 (8)	0.0009 (8)
N15	0.0532 (10)	0.0526 (10)	0.0655 (10)	−0.0005 (8)	−0.0131 (8)	−0.0008 (8)
C16	0.0512 (11)	0.0447 (10)	0.0514 (10)	−0.0019 (8)	0.0000 (9)	0.0019 (8)
C17	0.0486 (10)	0.0392 (10)	0.0476 (10)	−0.0049 (8)	−0.0003 (8)	−0.0004 (8)
C18	0.0639 (13)	0.0425 (10)	0.0588 (12)	−0.0007 (9)	−0.0058 (11)	0.0015 (9)
C19	0.0796 (16)	0.0403 (11)	0.0655 (13)	0.0005 (11)	−0.0034 (12)	−0.0019 (10)
C20	0.0820 (16)	0.0484 (12)	0.0628 (13)	−0.0121 (11)	−0.0087 (12)	−0.0097 (10)
C21	0.0634 (14)	0.0566 (13)	0.0583 (12)	−0.0105 (11)	−0.0094 (11)	−0.0029 (10)

Geometric parameters (Å, º)

N1—C5	1.341 (2)	C11—H11	0.93 (3)
N1—N2	1.361 (2)	N12—O2	1.214 (3)
N1—C6	1.438 (2)	N12—O1	1.223 (2)
N2—N3	1.290 (2)	N13—N14	1.381 (2)
N3—N4	1.358 (3)	N13—C17	1.382 (2)
N4—C5	1.305 (3)	N14—N15	1.286 (2)
C5—N13	1.385 (2)	N15—C16	1.382 (3)
C6—C11	1.369 (3)	C16—C17	1.389 (3)
C6—C7	1.377 (3)	C16—C21	1.402 (3)
C7—C8	1.383 (3)	C17—C18	1.383 (3)
C7—H7	1.01 (3)	C18—C19	1.371 (3)
C8—C9	1.372 (3)	C18—H18	0.96 (2)
C8—H8	0.97 (2)	C19—C20	1.400 (4)
C9—C10	1.370 (3)	C19—H19	0.94 (3)
C9—N12	1.474 (3)	C20—C21	1.368 (3)
C10—C11	1.380 (3)	C20—H20	0.91 (3)
C10—H10	0.94 (2)	C21—H21	0.89 (2)
C5—N1—N2	106.83 (16)	O2—N12—O1	123.7 (2)
C5—N1—C6	133.39 (16)	O2—N12—C9	118.0 (2)
N2—N1—C6	119.73 (15)	O1—N12—C9	118.30 (19)
N3—N2—N1	106.48 (16)	N14—N13—C17	110.34 (15)
N2—N3—N4	111.32 (17)	N14—N13—C5	121.62 (16)
C5—N4—N3	105.19 (17)	C17—N13—C5	127.95 (16)
N4—C5—N1	110.18 (17)	N15—N14—N13	107.98 (16)
N4—C5—N13	124.16 (18)	N14—N15—C16	109.33 (16)
N1—C5—N13	125.66 (17)	N15—C16—C17	109.26 (17)
C11—C6—C7	122.08 (19)	N15—C16—C21	130.1 (2)
C11—C6—N1	118.68 (18)	C17—C16—C21	120.62 (19)
C7—C6—N1	119.19 (18)	N13—C17—C18	133.88 (19)
C6—C7—C8	118.8 (2)	N13—C17—C16	103.07 (16)
C6—C7—H7	120.4 (14)	C18—C17—C16	123.05 (18)
C8—C7—H7	120.8 (14)	C19—C18—C17	115.5 (2)
C9—C8—C7	118.5 (2)	C19—C18—H18	123.2 (15)
C9—C8—H8	119.2 (14)	C17—C18—H18	121.3 (15)
C7—C8—H8	122.2 (14)	C18—C19—C20	122.6 (2)
C10—C9—C8	123.02 (19)	C18—C19—H19	118.8 (16)
C10—C9—N12	118.26 (19)	C20—C19—H19	118.6 (16)
C8—C9—N12	118.71 (19)	C21—C20—C19	121.7 (2)
C9—C10—C11	118.2 (2)	C21—C20—H20	116.9 (17)
C9—C10—H10	120.5 (16)	C19—C20—H20	121.4 (17)
C11—C10—H10	121.2 (16)	C20—C21—C16	116.6 (2)
C6—C11—C10	119.4 (2)	C20—C21—H21	121.6 (16)
C6—C11—H11	119.4 (17)	C16—C21—H21	121.8 (16)
C10—C11—H11	121.2 (17)
C5—N1—N2—N3	−0.3 (2)	C10—C9—N12—O1	−169.48 (19)
C6—N1—N2—N3	177.32 (18)	C8—C9—N12—O1	10.0 (3)
N1—N2—N3—N4	0.2 (2)	N4—C5—N13—N14	−160.91 (19)
N2—N3—N4—C5	0.0 (2)	N1—C5—N13—N14	19.1 (3)
N3—N4—C5—N1	−0.1 (2)	N4—C5—N13—C17	15.3 (3)
N3—N4—C5—N13	179.84 (18)	N1—C5—N13—C17	−164.77 (19)
N2—N1—C5—N4	0.3 (2)	C17—N13—N14—N15	0.8 (2)
C6—N1—C5—N4	−176.9 (2)	C5—N13—N14—N15	177.54 (17)
N2—N1—C5—N13	−179.72 (18)	N13—N14—N15—C16	0.0 (2)
C6—N1—C5—N13	3.2 (3)	N14—N15—C16—C17	−0.7 (2)
C5—N1—C6—C11	−93.6 (3)	N14—N15—C16—C21	179.1 (2)
N2—N1—C6—C11	89.6 (2)	N14—N13—C17—C18	179.0 (2)
C5—N1—C6—C7	89.1 (3)	C5—N13—C17—C18	2.5 (4)
N2—N1—C6—C7	−87.7 (2)	N14—N13—C17—C16	−1.1 (2)
C11—C6—C7—C8	−0.2 (3)	C5—N13—C17—C16	−177.66 (18)
N1—C6—C7—C8	176.97 (18)	N15—C16—C17—N13	1.1 (2)
C6—C7—C8—C9	0.3 (3)	C21—C16—C17—N13	−178.74 (18)
C7—C8—C9—C10	0.2 (3)	N15—C16—C17—C18	−179.04 (19)
C7—C8—C9—N12	−179.31 (19)	C21—C16—C17—C18	1.1 (3)
C8—C9—C10—C11	−0.8 (3)	N13—C17—C18—C19	179.4 (2)
N12—C9—C10—C11	178.70 (19)	C16—C17—C18—C19	−0.4 (3)
C7—C6—C11—C10	−0.4 (3)	C17—C18—C19—C20	0.0 (3)
N1—C6—C11—C10	−177.60 (19)	C18—C19—C20—C21	−0.3 (4)
C9—C10—C11—C6	0.9 (3)	C19—C20—C21—C16	1.0 (4)
C10—C9—N12—O2	10.9 (3)	N15—C16—C21—C20	178.8 (2)
C8—C9—N12—O2	−169.6 (2)	C17—C16—C21—C20	−1.3 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C8—H8···O1^i	0.97 (2)	2.51 (2)	3.401 (3)	153.5 (19)
C10—H10···N4^ii	0.94 (2)	2.60 (3)	3.535 (3)	172 (2)

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