[2-(Benzotriazol-1-yl)eth­yl][2-(benzotriazol-2-yl)ethyl]amine

In the title compound, C₁₆H₁₇N₇, the dihedral angle between the two benzotriazole ring systems is 73.97 (4)°. N—H...N and C—H...N hydrogen bonds link the mol­ecules into a chain along the a axis. The packing is further stabilized by π–π stacking inter­actions involving two benzotriazole ring systems.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.059
• wR factor = 0.167
• Data-to-parameter ratio = 15.6

checkCIF/PLATON results

No syntax errors found



Alert level B
DIFMX01_ALERT_2_B  The maximum difference density is > 0.1*ZMAX*1.00
            _refine_diff_density_max given =      0.714
            Test value =      0.700
PLAT097_ALERT_2_B Maximum (Positive) Residual Density ............       0.71 e/A   3

Alert level C
DIFMX02_ALERT_1_C  The maximum difference density is > 0.1*ZMAX*0.75
            The relevant atom site should be identified.
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical .          ?
PLAT094_ALERT_2_C Ratio of Maximum / Minimum Residual Density ....       2.09
PLAT199_ALERT_1_C Check the Reported _cell_measurement_temperature        293 K
PLAT200_ALERT_1_C Check the Reported _diffrn_ambient_temperature .        293 K
PLAT230_ALERT_2_C Hirshfeld Test Diff for    C2     -   C3      ..       5.97 su

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

   4 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   4 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

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S1. Comment

Benzotriazole and its derivatives have good anti-wear properties, and they are well established corrosion inhibitors for copper and its alloys (Ren et al., 1994; Dugdale & Cotton, 1963). In view of these properties, the title compound, (I), was synthesized according to the literature procedure (Liao et al., 1998), and its crystal stucture is reported here.

The structural investigation of (I) indicates that the geometry around atom N4 is pyramidal (Fig. 1). The Csp³—N bond distances range from 1.455 (3) to 1.460 (2) Å (Table 1). The dihedral angle between the two benzotriazole ring systems is 73.97 (4)°. The N—Csp³—Csp³—N torsion angles [179.4 (2) and 58.6 (2)°] define the conformation of the central linkage.

In the crystal packing of (I), molecules translated one unit cell along the a direction are linked to form a chain via N—H···N and C—H···N hydrogen bonds (Table 2 and Fig. 2). The packing is further stabilized by π–π stacking interactions between the N1-benzotriazole ring system at (x, y, z) and the N5-benzotriazole ring system at the symmetry position (x − 1, 1/2 − y, z − 1/2) [centroid···centroid distance 3.718 (2) Å].

S2. Experimental

Compound (I) was synthesized according to the literature procedure of Liao et al. (1998). Single crystals of (I) suitable for X-ray diffraction were obtained by slow evaporation of an ethanol solution at room temperature.

S3. Refinement

Atom H4A was located in a difference Fourier map and refined isotropically. All other H atoms were placed in geometrically idealized positions and constrained to ride on their parent atoms, with C—H_methylene = 0.97 Å and C—H_aromatic = 0.93 Å, and with U_iso(H) = 1.2U_eq(C). Three highest peaks in the final difference map indicated disorder for the C7–C8–N4 chain segment. However, refinement based on a disordered chain segment model led to very high displacement parameters.

Computing details

Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: SHELXL97 and PLATON.

Figures

	Fig. 1. The structure of (I). Displacement ellipsoids are drawn at the 30% probability level.
	Fig. 2. Part of the crystal packing of (I), showing a hydrogen-bonded (dashed lines) chain along the a axis and π–π interactions. For clarity, only H atoms involved in the hydrogen bonding are shown. Atoms labelled with the suffixes a, b and c are generated by the symmetry operations (1 + x, y, z), (x − 1, y, z) and (x − 1, 1/2 − y, z − 1/2), respectively.

(2-Benzotriazol-1-ylethyl)[2-(benzotriazol-2-yl)ethyl]amine

Crystal data

C16H17N7	F(000) = 648
Mr = 307.37	Dx = 1.339 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 5137 reflections
a = 6.2180 (16) Å	θ = 2.2–26.6°
b = 24.893 (6) Å	µ = 0.09 mm^−1
c = 10.020 (3) Å	T = 293 K
β = 100.650 (4)°	Block, colourless
V = 1524.2 (7) Å^3	0.40 × 0.30 × 0.20 mm
Z = 4

Data collection

Bruker SMART APEX CCD area-detector diffractometer	3313 independent reflections
Radiation source: fine focus sealed Siemens Mo tube	2647 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.029
ϕ and ω scans	θmax = 27.0°, θmin = 2.2°
Absorption correction: multi-scan (SADABS; Sheldrick, 2003)	h = −7→7
Tmin = 0.966, Tmax = 0.983	k = −31→31
12667 measured reflections	l = −12→12

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)] = 0.059	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.167	H-atom parameters constrained
S = 1.04	w = 1/[σ^2(Fo^2) + (0.0783P)^2 + 0.5802P] where P = (Fo^2 + 2Fc^2)/3
3313 reflections	(Δ/σ)max = 0.001
212 parameters	Δρmax = 0.71 e Å^−3
0 restraints	Δρmin = −0.34 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
C1	0.4534 (3)	0.08822 (8)	−0.07060 (19)	0.0475 (4)
C2	0.5901 (3)	0.07635 (10)	−0.1622 (2)	0.0605 (6)
H2	0.7104	0.0975	−0.1701	0.073*
C3	0.5357 (4)	0.03163 (11)	−0.2395 (3)	0.0698 (6)
H3	0.6220	0.0221	−0.3023	0.084*
C4	0.3540 (4)	−0.00071 (9)	−0.2283 (2)	0.0655 (6)
H4	0.3241	−0.0308	−0.2837	0.079*
C5	0.2213 (3)	0.01082 (8)	−0.1387 (2)	0.0557 (5)
H5	0.1020	−0.0107	−0.1308	0.067*
C6	0.2735 (3)	0.05673 (8)	−0.05871 (19)	0.0456 (4)
C7	0.6043 (4)	0.17235 (9)	0.0618 (3)	0.0700 (7)
H7A	0.5284	0.2021	0.0952	0.084*
H7B	0.6606	0.1848	−0.0168	0.084*
C8	0.7878 (4)	0.15548 (9)	0.1679 (2)	0.0635 (6)
H8A	0.7317	0.1434	0.2469	0.076*
H8B	0.8629	0.1255	0.1348	0.076*
C9	0.9046 (3)	0.23121 (8)	0.3222 (2)	0.0533 (5)
H9A	0.8801	0.2075	0.3947	0.064*
H9B	0.7742	0.2529	0.2951	0.064*
C10	1.0961 (3)	0.26725 (8)	0.37328 (19)	0.0522 (5)
H10A	1.0655	0.2881	0.4494	0.063*
H10B	1.2243	0.2454	0.4054	0.063*
C11	1.2935 (3)	0.33659 (8)	0.11778 (19)	0.0493 (5)
C12	1.4260 (4)	0.35054 (11)	0.0230 (2)	0.0705 (7)
H12	1.5568	0.3329	0.0202	0.085*
C13	1.3519 (5)	0.39136 (13)	−0.0644 (2)	0.0832 (9)
H13	1.4341	0.4013	−0.1291	0.100*
C14	1.1566 (5)	0.41891 (12)	−0.0602 (3)	0.0844 (9)
H14	1.1133	0.4463	−0.1224	0.101*
C15	1.0285 (4)	0.40691 (10)	0.0317 (2)	0.0698 (6)
H15	0.9007	0.4259	0.0351	0.084*
C16	1.0990 (3)	0.36421 (8)	0.12188 (19)	0.0485 (4)
N1	0.4503 (3)	0.12848 (7)	0.02125 (17)	0.0554 (4)
N2	0.2816 (3)	0.12158 (7)	0.08639 (18)	0.0602 (5)
N3	0.1737 (3)	0.07870 (7)	0.03929 (18)	0.0566 (4)
N4	0.9424 (3)	0.19926 (7)	0.20710 (17)	0.0549 (4)
H4A	1.081 (4)	0.1847 (10)	0.230 (3)	0.076 (8)*
N5	1.3185 (3)	0.29758 (6)	0.21334 (17)	0.0500 (4)
N6	1.1426 (2)	0.30373 (6)	0.26822 (15)	0.0430 (4)
N7	1.0046 (3)	0.34226 (6)	0.22029 (17)	0.0491 (4)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0399 (9)	0.0522 (10)	0.0473 (10)	−0.0038 (8)	0.0003 (8)	0.0164 (8)
C2	0.0469 (11)	0.0695 (14)	0.0662 (13)	−0.0010 (10)	0.0128 (10)	0.0207 (11)
C3	0.0687 (14)	0.0789 (16)	0.0680 (14)	0.0186 (12)	0.0287 (12)	0.0172 (12)
C4	0.0779 (15)	0.0550 (12)	0.0637 (13)	0.0062 (11)	0.0132 (11)	0.0003 (10)
C5	0.0547 (11)	0.0496 (11)	0.0614 (12)	−0.0083 (9)	0.0073 (9)	0.0040 (9)
C6	0.0393 (9)	0.0506 (10)	0.0455 (10)	−0.0038 (7)	0.0044 (7)	0.0091 (8)
C7	0.0708 (14)	0.0579 (13)	0.0715 (15)	−0.0241 (11)	−0.0125 (12)	0.0160 (11)
C8	0.0634 (13)	0.0580 (12)	0.0649 (13)	−0.0160 (10)	0.0012 (11)	0.0062 (10)
C9	0.0518 (11)	0.0591 (12)	0.0503 (11)	−0.0089 (9)	0.0128 (9)	0.0067 (9)
C10	0.0607 (12)	0.0541 (11)	0.0401 (10)	−0.0068 (9)	0.0048 (8)	0.0015 (8)
C11	0.0496 (11)	0.0540 (11)	0.0448 (10)	−0.0123 (8)	0.0101 (8)	−0.0121 (8)
C12	0.0668 (14)	0.0863 (17)	0.0650 (14)	−0.0222 (12)	0.0290 (11)	−0.0193 (13)
C13	0.099 (2)	0.105 (2)	0.0490 (13)	−0.0453 (18)	0.0233 (13)	−0.0035 (14)
C14	0.098 (2)	0.0897 (18)	0.0582 (14)	−0.0338 (16)	−0.0050 (14)	0.0222 (13)
C15	0.0678 (14)	0.0662 (14)	0.0701 (15)	−0.0091 (11)	−0.0012 (11)	0.0135 (12)
C16	0.0505 (10)	0.0499 (10)	0.0435 (10)	−0.0096 (8)	0.0045 (8)	−0.0033 (8)
N1	0.0532 (10)	0.0578 (10)	0.0508 (9)	−0.0153 (8)	−0.0023 (7)	0.0070 (8)
N2	0.0615 (11)	0.0638 (11)	0.0541 (10)	−0.0107 (9)	0.0079 (8)	−0.0011 (8)
N3	0.0515 (9)	0.0623 (10)	0.0570 (10)	−0.0110 (8)	0.0126 (8)	−0.0012 (8)
N4	0.0542 (10)	0.0576 (10)	0.0518 (10)	−0.0169 (8)	0.0072 (8)	−0.0043 (8)
N5	0.0429 (8)	0.0515 (9)	0.0561 (9)	−0.0031 (7)	0.0100 (7)	−0.0080 (7)
N6	0.0424 (8)	0.0448 (8)	0.0415 (8)	−0.0041 (6)	0.0067 (6)	−0.0039 (6)
N7	0.0465 (9)	0.0498 (9)	0.0513 (9)	0.0011 (7)	0.0102 (7)	−0.0004 (7)

Geometric parameters (Å, º)

C1—N1	1.363 (3)	C9—H9B	0.97
C1—C6	1.389 (3)	C10—N6	1.459 (2)
C1—C2	1.393 (3)	C10—H10A	0.97
C2—C3	1.363 (4)	C10—H10B	0.97
C2—H2	0.93	C11—N5	1.352 (3)
C3—C4	1.409 (3)	C11—C16	1.398 (3)
C3—H3	0.93	C11—C12	1.411 (3)
C4—C5	1.358 (3)	C12—C13	1.365 (4)
C4—H4	0.93	C12—H12	0.93
C5—C6	1.399 (3)	C13—C14	1.402 (4)
C5—H5	0.93	C13—H13	0.93
C6—N3	1.369 (3)	C14—C15	1.357 (4)
C7—N1	1.460 (2)	C14—H14	0.93
C7—C8	1.470 (3)	C15—C16	1.411 (3)
C7—H7A	0.97	C15—H15	0.93
C7—H7B	0.97	C16—N7	1.353 (2)
C8—N4	1.458 (3)	N1—N2	1.345 (3)
C8—H8A	0.97	N2—N3	1.302 (2)
C8—H8B	0.97	N4—H4A	0.92 (3)
C9—N4	1.455 (3)	N5—N6	1.321 (2)
C9—C10	1.503 (3)	N6—N7	1.317 (2)
C9—H9A	0.97
N1—C1—C6	104.18 (17)	N6—C10—H10A	109.2
N1—C1—C2	133.40 (19)	C9—C10—H10A	109.2
C6—C1—C2	122.4 (2)	N6—C10—H10B	109.2
C3—C2—C1	115.5 (2)	C9—C10—H10B	109.2
C3—C2—H2	122.3	H10A—C10—H10B	107.9
C1—C2—H2	122.3	N5—C11—C16	108.61 (17)
C2—C3—C4	122.7 (2)	N5—C11—C12	130.4 (2)
C2—C3—H3	118.7	C16—C11—C12	121.0 (2)
C4—C3—H3	118.7	C13—C12—C11	116.5 (2)
C5—C4—C3	121.8 (2)	C13—C12—H12	121.8
C5—C4—H4	119.1	C11—C12—H12	121.8
C3—C4—H4	119.1	C12—C13—C14	122.4 (2)
C4—C5—C6	116.5 (2)	C12—C13—H13	118.8
C4—C5—H5	121.7	C14—C13—H13	118.8
C6—C5—H5	121.7	C15—C14—C13	122.2 (2)
N3—C6—C1	108.36 (17)	C15—C14—H14	118.9
N3—C6—C5	130.51 (17)	C13—C14—H14	118.9
C1—C6—C5	121.13 (19)	C14—C15—C16	116.6 (3)
N1—C7—C8	111.67 (17)	C14—C15—H15	121.7
N1—C7—H7A	109.3	C16—C15—H15	121.7
C8—C7—H7A	109.3	N7—C16—C11	108.49 (17)
N1—C7—H7B	109.3	N7—C16—C15	130.2 (2)
C8—C7—H7B	109.3	C11—C16—C15	121.3 (2)
H7A—C7—H7B	107.9	N2—N1—C1	110.07 (15)
N4—C8—C7	111.50 (18)	N2—N1—C7	119.40 (19)
N4—C8—H8A	109.3	C1—N1—C7	130.4 (2)
C7—C8—H8A	109.3	N3—N2—N1	108.93 (17)
N4—C8—H8B	109.3	N2—N3—C6	108.44 (16)
C7—C8—H8B	109.3	C9—N4—C8	115.27 (18)
H8A—C8—H8B	108.0	C9—N4—H4A	107.3 (16)
N4—C9—C10	111.23 (16)	C8—N4—H4A	108.2 (16)
N4—C9—H9A	109.4	N6—N5—C11	102.46 (16)
C10—C9—H9A	109.4	N7—N6—N5	117.82 (15)
N4—C9—H9B	109.4	N7—N6—C10	120.90 (15)
C10—C9—H9B	109.4	N5—N6—C10	121.20 (16)
H9A—C9—H9B	108.0	N6—N7—C16	102.61 (15)
N6—C10—C9	112.08 (15)
N1—C1—C2—C3	−179.2 (2)	C6—C1—N1—N2	0.9 (2)
C6—C1—C2—C3	−0.1 (3)	C2—C1—N1—N2	−179.9 (2)
C1—C2—C3—C4	−0.1 (3)	C6—C1—N1—C7	176.01 (18)
C2—C3—C4—C5	−0.1 (4)	C2—C1—N1—C7	−4.7 (4)
C3—C4—C5—C6	0.5 (3)	C8—C7—N1—N2	90.2 (3)
N1—C1—C6—N3	−0.8 (2)	C8—C7—N1—C1	−84.6 (3)
C2—C1—C6—N3	179.89 (17)	C1—N1—N2—N3	−0.7 (2)
N1—C1—C6—C5	179.78 (17)	C7—N1—N2—N3	−176.42 (17)
C2—C1—C6—C5	0.4 (3)	N1—N2—N3—C6	0.2 (2)
C4—C5—C6—N3	−179.9 (2)	C1—C6—N3—N2	0.4 (2)
C4—C5—C6—C1	−0.6 (3)	C5—C6—N3—N2	179.8 (2)
N1—C7—C8—N4	179.4 (2)	C10—C9—N4—C8	167.99 (17)
N4—C9—C10—N6	58.6 (2)	C7—C8—N4—C9	92.9 (3)
N5—C11—C12—C13	177.9 (2)	C16—C11—N5—N6	−0.04 (19)
C16—C11—C12—C13	−1.0 (3)	C12—C11—N5—N6	−179.0 (2)
C11—C12—C13—C14	0.9 (4)	C11—N5—N6—N7	−0.1 (2)
C12—C13—C14—C15	0.3 (4)	C11—N5—N6—C10	176.56 (15)
C13—C14—C15—C16	−1.4 (4)	C9—C10—N6—N7	67.5 (2)
N5—C11—C16—N7	0.2 (2)	C9—C10—N6—N5	−109.1 (2)
C12—C11—C16—N7	179.26 (18)	N5—N6—N7—C16	0.2 (2)
N5—C11—C16—C15	−179.15 (18)	C10—N6—N7—C16	−176.48 (15)
C12—C11—C16—C15	0.0 (3)	C11—C16—N7—N6	−0.20 (19)
C14—C15—C16—N7	−177.9 (2)	C15—C16—N7—N6	179.0 (2)
C14—C15—C16—C11	1.2 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C8—H8B···N3^i	0.97	2.59	3.495 (3)	156
N4—H4A···N2^i	0.92 (3)	2.60 (3)	3.254 (3)	128 (2)

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