Buy article online - an online subscription or single-article purchase is required to access this article.
Download citation
Download citation
link to html
The title compound, C10H11ClN4O, displays the characteristic features of 1,2,4-triazole derivatives. The crystal structure is stabilized by N—H...O intermolecular hydrogen bonds.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536803015058/cv6206sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536803015058/cv6206Isup2.hkl
Contains datablock I

CCDC reference: 221685

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.005 Å
  • R factor = 0.062
  • wR factor = 0.205
  • Data-to-parameter ratio = 22.2

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry


Yellow Alert Alert Level C:
PLAT_420 Alert C D-H Without Acceptor N1 - H1 ... ?
0 Alert Level A = Potentially serious problem
0 Alert Level B = Potential problem
1 Alert Level C = Please check

Computing details top

Data collection: X-AREA (Stoe & Cie, 2002); cell refinement: X-AREA; data reduction: X-RED (Stoe & Cie, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPIII (Burnett & Johnson, 1996); software used to prepare material for publication: WinGX (Farrugia, 1999), PARST (Nardelli, 1995) and PLATON (Spek, 1997).

(I) top
Crystal data top
C10H11ClN4OF(000) = 496
Mr = 238.68Dx = 1.360 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 14391 reflections
a = 14.3423 (15) Åθ = 1.7–29.3°
b = 5.8708 (3) ŵ = 0.31 mm1
c = 15.2730 (14) ÅT = 293 K
β = 114.963 (7)°Prismatic, colourless
V = 1165.86 (17) Å30.60 × 0.46 × 0.28 mm
Z = 4
Data collection top
Stoe IPDS-II
diffractometer
3218 independent reflections
Radiation source: fine-focus sealed tube1519 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.000
Detector resolution: 6.67 pixels mm-1θmax = 29.4°, θmin = 2.7°
rotation method scansh = 1917
Absorption correction: integration
(X-RED; Stoe & Cie, 2002)
k = 08
Tmin = 0.839, Tmax = 0.923l = 020
3218 measured reflections
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)] = 0.063Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.205H-atom parameters constrained
S = 0.86 w = 1/[σ2(Fo2) + (0.1356P)2]
where P = (Fo2 + 2Fc2)/3
3218 reflections(Δ/σ)max < 0.001
145 parametersΔρmax = 0.51 e Å3
0 restraintsΔρmin = 0.43 e Å3
Special details top

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 (Å2) top
xyzUiso*/Ueq
C30.8370 (4)0.0088 (8)0.8114 (4)0.1042 (13)
H30.88820.09280.81490.125*
C40.8617 (3)0.1920 (7)0.8764 (3)0.0935 (11)
H40.92880.21210.92260.112*
O10.96137 (14)0.4083 (3)1.16108 (13)0.0729 (5)
C20.7405 (4)0.0218 (6)0.7443 (3)0.0943 (11)
H20.72490.14440.70200.113*
C70.8070 (3)0.5315 (5)0.9425 (2)0.0869 (10)
H7A0.88070.54480.98040.104*
H7B0.78240.67390.90840.104*
C100.89134 (17)0.2665 (4)1.13455 (14)0.0510 (5)
C50.7855 (2)0.3420 (5)0.87106 (18)0.0658 (7)
N30.88941 (15)0.0553 (3)1.16510 (13)0.0572 (5)
H3A0.94160.01031.20950.069*
C10.6664 (3)0.1265 (5)0.73876 (19)0.0751 (8)
C60.6870 (2)0.3086 (5)0.80052 (18)0.0664 (7)
H60.63480.40950.79490.080*
N20.79365 (13)0.2948 (3)1.06236 (12)0.0463 (4)
N10.75691 (18)0.4909 (3)1.00719 (13)0.0641 (6)
H10.71030.57791.01070.077*
N40.79494 (16)0.0470 (3)1.11810 (14)0.0587 (5)
C80.73907 (17)0.1019 (3)1.05554 (15)0.0479 (5)
Cl10.54065 (9)0.0838 (2)0.65249 (7)0.1302 (5)
C90.6299 (2)0.0695 (5)0.9878 (2)0.0744 (8)
H9A0.60510.20380.94910.112*
H9B0.58990.04231.02380.112*
H9C0.62400.05870.94680.112*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C30.120 (3)0.104 (3)0.129 (3)0.030 (3)0.092 (3)0.034 (3)
C40.0710 (18)0.116 (3)0.099 (2)0.0012 (19)0.0410 (17)0.039 (2)
O10.0712 (11)0.0676 (12)0.0576 (9)0.0243 (9)0.0056 (8)0.0055 (8)
C20.150 (3)0.078 (2)0.092 (2)0.003 (2)0.087 (3)0.0044 (18)
C70.116 (2)0.0664 (17)0.0601 (15)0.0331 (17)0.0200 (16)0.0120 (13)
C100.0567 (12)0.0469 (12)0.0383 (9)0.0031 (10)0.0092 (9)0.0048 (9)
C50.0733 (16)0.0670 (15)0.0564 (13)0.0108 (13)0.0268 (12)0.0164 (12)
N30.0581 (11)0.0478 (11)0.0489 (10)0.0041 (9)0.0062 (8)0.0058 (8)
C10.100 (2)0.0775 (19)0.0546 (14)0.0116 (17)0.0393 (15)0.0046 (13)
C60.0752 (16)0.0672 (16)0.0564 (13)0.0040 (13)0.0273 (12)0.0021 (12)
N20.0555 (10)0.0349 (8)0.0394 (8)0.0005 (7)0.0110 (7)0.0006 (6)
N10.0855 (14)0.0365 (9)0.0509 (10)0.0052 (9)0.0099 (10)0.0060 (8)
N40.0668 (12)0.0443 (10)0.0543 (10)0.0054 (9)0.0151 (9)0.0039 (8)
C80.0554 (12)0.0383 (10)0.0469 (10)0.0027 (9)0.0186 (9)0.0014 (8)
Cl10.1346 (9)0.1493 (11)0.0759 (6)0.0396 (8)0.0143 (6)0.0252 (6)
C90.0547 (14)0.0764 (18)0.0755 (17)0.0105 (13)0.0113 (12)0.0056 (14)
Geometric parameters (Å, º) top
C3—C21.341 (6)C5—C61.381 (4)
C3—C41.404 (6)N3—N41.375 (3)
C3—H30.9300N3—H3A0.8600
C4—C51.379 (5)C1—C61.373 (4)
C4—H40.9300C1—Cl11.746 (3)
O1—C101.234 (3)C6—H60.9300
C2—C11.349 (5)N2—C81.356 (3)
C2—H20.9300N2—N11.392 (2)
C7—N11.465 (4)N1—H10.8600
C7—C51.497 (4)N4—C81.293 (3)
C7—H7A0.9700C8—C91.480 (3)
C7—H7B0.9700C9—H9A0.9600
C10—N31.330 (3)C9—H9B0.9600
C10—N21.379 (3)C9—H9C0.9600
C2—C3—C4120.9 (4)N4—N3—H3A123.6
C2—C3—H3119.5C2—C1—C6121.6 (3)
C4—C3—H3119.5C2—C1—Cl1119.4 (3)
C5—C4—C3119.4 (3)C6—C1—Cl1119.0 (3)
C5—C4—H4120.3C1—C6—C5119.9 (3)
C3—C4—H4120.3C1—C6—H6120.0
C3—C2—C1119.5 (4)C5—C6—H6120.0
C3—C2—H2120.2C8—N2—C10108.65 (17)
C1—C2—H2120.2C8—N2—N1125.85 (18)
N1—C7—C5111.2 (2)C10—N2—N1125.49 (19)
N1—C7—H7A109.4N2—N1—C7112.0 (2)
C5—C7—H7A109.4N2—N1—H1124.0
N1—C7—H7B109.4C7—N1—H1124.0
C5—C7—H7B109.4C8—N4—N3104.91 (18)
H7A—C7—H7B108.0N4—C8—N2110.50 (19)
O1—C10—N3130.5 (2)N4—C8—C9124.9 (2)
O1—C10—N2126.4 (2)N2—C8—C9124.6 (2)
N3—C10—N2103.19 (18)C8—C9—H9A109.5
C4—C5—C6118.6 (3)C8—C9—H9B109.5
C4—C5—C7121.1 (3)H9A—C9—H9B109.5
C6—C5—C7120.2 (3)C8—C9—H9C109.5
C10—N3—N4112.71 (18)H9A—C9—H9C109.5
C10—N3—H3A123.6H9B—C9—H9C109.5
C2—C3—C4—C50.1 (5)O1—C10—N2—C8179.4 (2)
C4—C3—C2—C10.5 (5)N3—C10—N2—C81.2 (2)
C3—C4—C5—C61.0 (4)O1—C10—N2—N10.6 (4)
C3—C4—C5—C7176.3 (3)N3—C10—N2—N1180.0 (2)
N1—C7—C5—C4109.9 (3)C8—N2—N1—C7113.2 (3)
N1—C7—C5—C667.4 (3)C10—N2—N1—C768.2 (3)
O1—C10—N3—N4178.6 (2)C5—C7—N1—N262.5 (3)
N2—C10—N3—N42.0 (2)C10—N3—N4—C82.0 (3)
C3—C2—C1—C60.3 (5)N3—N4—C8—N21.1 (2)
C3—C2—C1—Cl1179.1 (3)N3—N4—C8—C9179.5 (2)
C2—C1—C6—C50.6 (4)C10—N2—C8—N40.0 (3)
Cl1—C1—C6—C5178.2 (2)N1—N2—C8—N4178.8 (2)
C4—C5—C6—C11.2 (4)C10—N2—C8—C9178.3 (2)
C7—C5—C6—C1176.1 (2)N1—N2—C8—C90.5 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N3—H3A···O1i0.861.942.752 (2)158
Symmetry code: (i) x+2, y1/2, z+5/2.
 

Subscribe to Acta Crystallographica Section E: Crystallographic Communications

The full text of this article is available to subscribers to the journal.

If you have already registered and are using a computer listed in your registration details, please email support@iucr.org for assistance.

Buy online

You may purchase this article in PDF and/or HTML formats. For purchasers in the European Community who do not have a VAT number, VAT will be added at the local rate. Payments to the IUCr are handled by WorldPay, who will accept payment by credit card in several currencies. To purchase the article, please complete the form below (fields marked * are required), and then click on `Continue'.
E-mail address* 
Repeat e-mail address* 
(for error checking) 

Format*   PDF (US $40)
   HTML (US $40)
   PDF+HTML (US $50)
In order for VAT to be shown for your country javascript needs to be enabled.

VAT number 
(non-UK EC countries only) 
Country* 
 

Terms and conditions of use
Contact us

Follow Acta Cryst. E
Sign up for e-alerts
Follow Acta Cryst. on Twitter
Follow us on facebook
Sign up for RSS feeds