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The title compound, C13H10N6O2, which was synthesized by condensation of 1-hydroxy­benzotriazole with dichloro­methane at 273 K, is a by-product in peptide synthesis. The two ring systems form a dihedral angle of 53.90 (4)°, and π–π stacking inter­actions are found in the crystal structure.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S160053680604061X/cf2044sup1.cif
Contains datablocks I, Raxis

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S160053680604061X/cf2044Isup2.hkl
Contains datablock I

CCDC reference: 627444

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.003 Å
  • R factor = 0.041
  • wR factor = 0.099
  • Data-to-parameter ratio = 14.9

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ? PLAT230_ALERT_2_C Hirshfeld Test Diff for N3 - C6 .. 6.82 su
Alert level G PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature 293 K PLAT200_ALERT_1_G Check the Reported _diffrn_ambient_temperature . 293 K
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 2 ALERT level C = Check and explain 2 ALERT level G = General alerts; check 3 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 top

Data collection: SMART (Bruker, 2003); cell refinement: SAINT-Plus (Bruker, 2003); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXTL (Bruker, 2005); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

(I) top
Crystal data top
C13H10N6O2F(000) = 584
Mr = 282.27Dx = 1.458 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 1892 reflections
a = 7.9369 (8) Åθ = 3.0–24.5°
b = 23.343 (2) ŵ = 0.11 mm1
c = 7.9678 (9) ÅT = 293 K
β = 119.385 (2)°Block, colorless
V = 1286.3 (2) Å30.42 × 0.36 × 0.22 mm
Z = 4
Data collection top
Bruker AXS SMART 1000 CCD
diffractometer
2834 independent reflections
Radiation source: fine-focus sealed tube1494 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.038
ω scansθmax = 27.2°, θmin = 3.0°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 810
Tmin = 0.957, Tmax = 0.977k = 2629
7675 measured reflectionsl = 105
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.041Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.099H-atom parameters constrained
S = 1.01 w = 1/[σ2(Fo2) + (0.0418P)2 + 0.0025P]
where P = (Fo2 + 2Fc2)/3
2834 reflections(Δ/σ)max < 0.001
190 parametersΔρmax = 0.16 e Å3
0 restraintsΔρmin = 0.15 e Å3
Special details top

Experimental. 1H NMR(THF, 500 Hz,, p.p.m.): 6.92 (m, 4H), 6.48 (m, 2H), 6.31 (m, 2H), 5.35 (s, 2H); 13 C NMR(THF, 500 Hz,, p.p.m.): 144.5 (2 C, C1, C7), 129.3 (2 C, C6, C12), 129.0 (2 C, C2, C8), 125.6 (2 C, C3, C9), 120.8 (2 C, C5, C11), 110.5(2 C, C4, C10),107.1 (1 C, C13); EI—MS m/z (%): 282(M+,24).

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 &gt; 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 (Å2) top
xyzUiso*/Ueq
C10.6994 (3)0.23229 (7)0.0173 (3)0.0463 (4)
C20.5257 (3)0.22625 (9)0.1848 (3)0.0644 (5)
H20.47360.19050.23510.077*
C30.4342 (3)0.27631 (10)0.2729 (3)0.0747 (6)
H30.31600.27470.38620.090*
C40.5155 (3)0.32955 (9)0.1955 (4)0.0744 (6)
H40.44970.36250.25990.089*
C50.6856 (3)0.33513 (8)0.0310 (3)0.0635 (6)
H50.73720.37100.01870.076*
C60.7802 (3)0.28492 (7)0.0608 (3)0.0479 (5)
C71.1849 (2)0.06522 (7)0.4580 (3)0.0432 (4)
C81.1635 (3)0.10775 (7)0.5677 (3)0.0516 (5)
H81.12220.14450.52070.062*
C91.2074 (3)0.09186 (8)0.7496 (3)0.0573 (5)
H91.19700.11890.82980.069*
C101.2674 (3)0.03627 (8)0.8197 (3)0.0589 (5)
H101.29400.02740.94400.071*
C111.2878 (3)0.00489 (8)0.7109 (3)0.0562 (5)
H111.32820.04170.75840.067*
C121.2457 (2)0.01016 (7)0.5249 (3)0.0459 (4)
C130.9068 (3)0.10978 (7)0.0205 (3)0.0579 (5)
H13A0.85400.07160.01990.069*
H13B0.88150.13130.09370.069*
N10.8309 (2)0.19549 (5)0.1111 (2)0.0513 (4)
N20.9802 (2)0.22171 (6)0.2600 (2)0.0584 (4)
N30.9509 (2)0.27676 (6)0.2295 (2)0.0595 (4)
N41.1548 (2)0.06223 (6)0.2754 (2)0.0493 (4)
N51.1993 (2)0.01055 (6)0.2323 (2)0.0571 (4)
N61.2528 (2)0.02180 (6)0.3828 (2)0.0591 (4)
O10.81300 (18)0.13679 (4)0.11101 (19)0.0580 (4)
O21.10851 (19)0.10585 (5)0.14392 (18)0.0559 (4)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0488 (12)0.0458 (10)0.0489 (12)0.0006 (9)0.0275 (11)0.0019 (9)
C20.0530 (13)0.0711 (13)0.0675 (15)0.0123 (10)0.0285 (13)0.0063 (12)
C30.0508 (13)0.0971 (16)0.0675 (15)0.0078 (12)0.0222 (12)0.0101 (14)
C40.0689 (16)0.0672 (14)0.0875 (18)0.0194 (12)0.0386 (15)0.0202 (13)
C50.0722 (15)0.0499 (12)0.0759 (16)0.0064 (10)0.0421 (14)0.0040 (11)
C60.0543 (12)0.0442 (10)0.0499 (12)0.0010 (9)0.0293 (11)0.0002 (9)
C70.0471 (11)0.0444 (10)0.0391 (11)0.0061 (8)0.0219 (9)0.0003 (9)
C80.0621 (12)0.0465 (10)0.0441 (11)0.0020 (9)0.0245 (10)0.0023 (9)
C90.0647 (14)0.0619 (12)0.0448 (12)0.0031 (10)0.0265 (11)0.0076 (10)
C100.0652 (13)0.0696 (13)0.0413 (12)0.0024 (10)0.0257 (11)0.0055 (10)
C110.0587 (14)0.0527 (11)0.0527 (13)0.0034 (9)0.0238 (11)0.0116 (10)
C120.0458 (11)0.0458 (10)0.0439 (11)0.0027 (8)0.0203 (10)0.0012 (9)
C130.0815 (16)0.0460 (11)0.0414 (11)0.0010 (10)0.0264 (12)0.0033 (9)
N10.0607 (10)0.0361 (8)0.0526 (10)0.0051 (7)0.0242 (9)0.0033 (8)
N20.0698 (11)0.0477 (9)0.0497 (10)0.0047 (8)0.0231 (9)0.0037 (8)
N30.0735 (12)0.0421 (8)0.0583 (11)0.0040 (8)0.0287 (10)0.0042 (8)
N40.0692 (11)0.0385 (8)0.0431 (9)0.0007 (7)0.0300 (9)0.0020 (7)
N50.0770 (12)0.0459 (9)0.0545 (11)0.0029 (8)0.0370 (10)0.0036 (8)
N60.0746 (12)0.0474 (9)0.0562 (11)0.0054 (8)0.0328 (10)0.0014 (9)
O10.0784 (10)0.0370 (7)0.0676 (10)0.0063 (6)0.0430 (8)0.0016 (6)
O20.0741 (10)0.0497 (7)0.0512 (8)0.0025 (6)0.0364 (8)0.0066 (6)
Geometric parameters (Å, º) top
C1—N11.351 (2)C9—C101.401 (2)
C1—C21.378 (2)C9—H90.9300
C1—C61.384 (2)C10—C111.356 (2)
C2—C31.373 (3)C10—H100.9300
C2—H20.9300C11—C121.395 (2)
C3—C41.397 (3)C11—H110.9300
C3—H30.9300C12—N61.380 (2)
C4—C51.349 (3)C13—O21.412 (2)
C4—H40.9300C13—O11.4139 (19)
C5—C61.391 (2)C13—H13A0.9700
C5—H50.9300C13—H13B0.9700
C6—N31.375 (2)N1—N21.3444 (19)
C7—N41.355 (2)N1—O11.3774 (15)
C7—C121.385 (2)N2—N31.3074 (19)
C7—C81.387 (2)N4—N51.3479 (17)
C8—C91.365 (2)N4—O21.3754 (16)
C8—H80.9300N5—N61.2996 (19)
N1—C1—C2134.63 (17)C11—C10—C9121.72 (18)
N1—C1—C6102.06 (16)C11—C10—H10119.1
C2—C1—C6123.31 (17)C9—C10—H10119.1
C3—C2—C1115.79 (19)C10—C11—C12117.34 (16)
C3—C2—H2122.1C10—C11—H11121.3
C1—C2—H2122.1C12—C11—H11121.3
C2—C3—C4121.2 (2)N6—C12—C7109.45 (15)
C2—C3—H3119.4N6—C12—C11130.60 (16)
C4—C3—H3119.4C7—C12—C11119.95 (17)
C5—C4—C3122.68 (19)O2—C13—O1112.00 (14)
C5—C4—H4118.7O2—C13—H13A109.2
C3—C4—H4118.7O1—C13—H13A109.2
C4—C5—C6117.03 (19)O2—C13—H13B109.2
C4—C5—H5121.5O1—C13—H13B109.2
C6—C5—H5121.5H13A—C13—H13B107.9
N3—C6—C1109.46 (15)N2—N1—C1113.42 (13)
N3—C6—C5130.52 (18)N2—N1—O1119.95 (14)
C1—C6—C5120.01 (18)C1—N1—O1126.24 (15)
N4—C7—C12102.10 (14)N3—N2—N1106.50 (14)
N4—C7—C8134.58 (16)N2—N3—C6108.54 (14)
C12—C7—C8123.31 (16)N5—N4—C7112.92 (14)
C9—C8—C7115.37 (16)N5—N4—O2118.29 (13)
C9—C8—H8122.3C7—N4—O2128.30 (13)
C7—C8—H8122.3N6—N5—N4107.02 (13)
C8—C9—C10122.31 (18)N5—N6—C12108.45 (13)
C8—C9—H9118.8N1—O1—C13111.33 (12)
C10—C9—H9118.8N4—O2—C13111.50 (12)
N1—C1—C2—C3179.29 (18)C6—C1—N1—N21.23 (18)
C6—C1—C2—C30.1 (3)C2—C1—N1—O15.4 (3)
C1—C2—C3—C40.3 (3)C6—C1—N1—O1173.97 (14)
C2—C3—C4—C50.5 (3)C1—N1—N2—N31.30 (19)
C3—C4—C5—C60.3 (3)O1—N1—N2—N3174.55 (13)
N1—C1—C6—N30.70 (18)N1—N2—N3—C60.77 (19)
C2—C1—C6—N3178.74 (15)C1—C6—N3—N20.0 (2)
N1—C1—C6—C5179.74 (15)C5—C6—N3—N2178.87 (17)
C2—C1—C6—C50.3 (3)C12—C7—N4—N52.08 (18)
C4—C5—C6—N3178.69 (18)C8—C7—N4—N5179.25 (18)
C4—C5—C6—C10.1 (3)C12—C7—N4—O2173.90 (15)
N4—C7—C8—C9178.57 (18)C8—C7—N4—O27.4 (3)
C12—C7—C8—C90.1 (3)C7—N4—N5—N62.14 (19)
C7—C8—C9—C100.8 (3)O2—N4—N5—N6174.85 (14)
C8—C9—C10—C110.9 (3)N4—N5—N6—C121.18 (19)
C9—C10—C11—C120.3 (3)C7—C12—N6—N50.1 (2)
N4—C7—C12—N61.28 (18)C11—C12—N6—N5179.58 (18)
C8—C7—C12—N6179.85 (15)N2—N1—O1—C1391.06 (18)
N4—C7—C12—C11178.43 (16)C1—N1—O1—C1396.63 (18)
C8—C7—C12—C110.4 (3)O2—C13—O1—N179.77 (16)
C10—C11—C12—N6180.00 (17)N5—N4—O2—C1393.92 (17)
C10—C11—C12—C70.4 (3)C7—N4—O2—C1394.65 (19)
C2—C1—N1—N2178.12 (18)O1—C13—O2—N477.63 (15)
 

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