Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805029685/ci6647sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536805029685/ci6647Isup2.hkl |
CCDC reference: 287512
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (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
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.
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—Hmethylene = 0.97 Å and C—Haromatic = 0.93 Å, and with Uiso(H) = 1.2Ueq(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.
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.
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) Å3 | 0.40 × 0.30 × 0.20 mm |
Z = 4 |
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 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)] = 0.059 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.167 | H-atom parameters constrained |
S = 1.04 | w = 1/[σ2(Fo2) + (0.0783P)2 + 0.5802P] where P = (Fo2 + 2Fc2)/3 |
3313 reflections | (Δ/σ)max = 0.001 |
212 parameters | Δρmax = 0.71 e Å−3 |
0 restraints | Δρmin = −0.34 e Å−3 |
C16H17N7 | V = 1524.2 (7) Å3 |
Mr = 307.37 | Z = 4 |
Monoclinic, P21/c | Mo Kα radiation |
a = 6.2180 (16) Å | µ = 0.09 mm−1 |
b = 24.893 (6) Å | T = 293 K |
c = 10.020 (3) Å | 0.40 × 0.30 × 0.20 mm |
β = 100.650 (4)° |
Bruker SMART APEX CCD area-detector diffractometer | 3313 independent reflections |
Absorption correction: multi-scan (SADABS; Sheldrick, 2003) | 2647 reflections with I > 2σ(I) |
Tmin = 0.966, Tmax = 0.983 | Rint = 0.029 |
12667 measured reflections |
R[F2 > 2σ(F2)] = 0.059 | 0 restraints |
wR(F2) = 0.167 | H-atom parameters constrained |
S = 1.04 | Δρmax = 0.71 e Å−3 |
3313 reflections | Δρmin = −0.34 e Å−3 |
212 parameters |
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. |
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) |
U11 | U22 | U33 | U12 | U13 | U23 | |
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) |
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) |
D—H···A | D—H | H···A | D···A | D—H···A |
C8—H8B···N3i | 0.97 | 2.59 | 3.495 (3) | 156 |
N4—H4A···N2i | 0.92 (3) | 2.60 (3) | 3.254 (3) | 128 (2) |
Symmetry code: (i) x+1, y, z. |
Experimental details
Crystal data | |
Chemical formula | C16H17N7 |
Mr | 307.37 |
Crystal system, space group | Monoclinic, P21/c |
Temperature (K) | 293 |
a, b, c (Å) | 6.2180 (16), 24.893 (6), 10.020 (3) |
β (°) | 100.650 (4) |
V (Å3) | 1524.2 (7) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.09 |
Crystal size (mm) | 0.40 × 0.30 × 0.20 |
Data collection | |
Diffractometer | Bruker SMART APEX CCD area-detector diffractometer |
Absorption correction | Multi-scan (SADABS; Sheldrick, 2003) |
Tmin, Tmax | 0.966, 0.983 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 12667, 3313, 2647 |
Rint | 0.029 |
(sin θ/λ)max (Å−1) | 0.639 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.059, 0.167, 1.04 |
No. of reflections | 3313 |
No. of parameters | 212 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.71, −0.34 |
Computer programs: SMART (Bruker, 2001), SAINT (Bruker, 2001), SAINT, SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), PLATON (Spek, 2003), SHELXL97 and PLATON.
C1—N1 | 1.363 (3) | C10—N6 | 1.459 (2) |
C6—N3 | 1.369 (3) | C11—N5 | 1.352 (3) |
C7—N1 | 1.460 (2) | C16—N7 | 1.353 (2) |
C7—C8 | 1.470 (3) | N1—N2 | 1.345 (3) |
C8—N4 | 1.458 (3) | N2—N3 | 1.302 (2) |
C9—N4 | 1.455 (3) | N5—N6 | 1.321 (2) |
C9—C10 | 1.503 (3) | N6—N7 | 1.317 (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) |
D—H···A | D—H | H···A | D···A | D—H···A |
C8—H8B···N3i | 0.97 | 2.59 | 3.495 (3) | 156 |
N4—H4A···N2i | 0.92 (3) | 2.60 (3) | 3.254 (3) | 128 (2) |
Symmetry code: (i) x+1, y, z. |
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].