1-(3-Nitro­phen­yl)-3-(1H-1,2,4-triazol-1-yl)propan-1-one

In the title compound, C₁₁H₁₀N₄O₃, the substituted phen­yl ring and the triazole ring make a dihedral angle of 59.7 (2)°. The mol­ecules are linked into zigzag chains by inter­molecular C—H...O hydrogen bonds. These chains are further connected through C—H...N hydrogen bonds to build up a three-dimensional network.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.004 Å
• R factor = 0.038
• wR factor = 0.092
• Data-to-parameter ratio = 7.5

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical .          ?
PLAT089_ALERT_3_C Poor Data / Parameter Ratio (Zmax .LT. 18) .....       7.45
PLAT199_ALERT_1_C Check the Reported _cell_measurement_temperature        293 K
PLAT200_ALERT_1_C Check the Reported _diffrn_ambient_temperature .        293 K
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for         N1
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for         N4
PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor ....       2.21

Alert level G
REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is
            correct. If it is not, please give the correct count in the
            _publ_section_exptl_refinement section of the submitted CIF.
           From the CIF: _diffrn_reflns_theta_max           26.02
           From the CIF: _reflns_number_total               1215
           Count of symmetry unique reflns         1217
           Completeness (_total/calc)             99.84%
           TEST3: Check Friedels for noncentro structure
           Estimate of Friedel pairs measured         0
           Fraction of Friedel pairs measured     0.000
           Are heavy atom types Z>Si present         no

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

   3 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   3 ALERT type 2 Indicator that the structure model may be wrong or deficient
   1 ALERT type 3 Indicator that the structure quality may be low
   1 ALERT type 4 Improvement, methodology, query or suggestion

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Computing details

Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 1997); program(s) used to refine structure: SHELXTL; molecular graphics: ORTEPIII (Farrugia, 1997), PLATON (Spek, 2003) and SHELXTL; software used to prepare material for publication: SHELXTL, PARST (Nardelli, 1995) and PLATON.

1-(3-Nitrophenyl)-3-(1H-1,2,4-triazol-1-yl)propan-1-one

Crystal data

C11H10N4O3	F(000) = 512
Mr = 246.23	Dx = 1.412 Mg m^−3
Orthorhombic, Pca21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2ac	Cell parameters from 1871 reflections
a = 26.334 (8) Å	θ = 2.6–22.3°
b = 4.5962 (13) Å	µ = 0.11 mm^−1
c = 9.570 (3) Å	T = 293 K
V = 1158.4 (6) Å^3	Column, colourless
Z = 4	0.26 × 0.24 × 0.13 mm

Data collection

Siemens SMART 1000 CCD area-detector diffractometer	1215 independent reflections
Radiation source: fine-focus sealed tube	1093 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.023
Detector resolution: 8.33 pixels mm^-1	θmax = 26.0°, θmin = 1.6°
ω scans	h = −31→32
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	k = −5→5
Tmin = 0.973, Tmax = 0.986	l = −11→11
5794 measured reflections

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)] = 0.038	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.092	H-atom parameters constrained
S = 1.14	w = 1/[σ^2(Fo^2) + (0.0426P)^2 + 0.1225P] where P = (Fo^2 + 2Fc^2)/3
1215 reflections	(Δ/σ)max < 0.001
163 parameters	Δρmax = 0.14 e Å^−3
1 restraint	Δρmin = −0.13 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
O1	0.16810 (9)	−0.0697 (10)	0.1654 (4)	0.1289 (13)
O2	0.14445 (9)	0.2662 (7)	0.3039 (3)	0.1000 (9)
O3	0.34668 (8)	−0.2138 (5)	0.0558 (3)	0.0746 (7)
N1	0.49112 (7)	0.1405 (5)	−0.0004 (3)	0.0560 (6)
N2	0.55200 (11)	0.3987 (8)	−0.0894 (4)	0.0934 (11)
N3	0.52309 (10)	0.1932 (8)	0.1071 (3)	0.0858 (10)
N4	0.17699 (9)	0.1252 (7)	0.2458 (3)	0.0713 (8)
C1	0.26751 (9)	0.0620 (6)	0.1962 (3)	0.0517 (6)
H1A	0.2587	−0.0751	0.1289	0.062*
C2	0.23060 (9)	0.1958 (6)	0.2745 (3)	0.0542 (7)
C3	0.24159 (11)	0.3947 (6)	0.3773 (3)	0.0618 (8)
H3B	0.2159	0.4834	0.4285	0.074*
C4	0.29223 (11)	0.4592 (7)	0.4023 (4)	0.0685 (8)
H4A	0.3008	0.5877	0.4736	0.082*
C5	0.32982 (10)	0.3346 (6)	0.3225 (3)	0.0576 (7)
H5A	0.3635	0.3854	0.3382	0.069*
C6	0.31812 (9)	0.1334 (6)	0.2185 (3)	0.0473 (6)
C7	0.35737 (9)	−0.0023 (6)	0.1263 (3)	0.0496 (6)
C8	0.40862 (9)	0.1342 (6)	0.1182 (3)	0.0537 (7)
H8A	0.4233	0.1393	0.2111	0.064*
H8B	0.4050	0.3335	0.0864	0.064*
C9	0.44446 (10)	−0.0241 (6)	0.0214 (3)	0.0611 (8)
H9A	0.4527	−0.2127	0.0609	0.073*
H9B	0.4279	−0.0559	−0.0678	0.073*
C10	0.55876 (12)	0.3483 (9)	0.0459 (4)	0.0883 (12)
H10A	0.5869	0.4181	0.0943	0.106*
C11	0.50887 (13)	0.2660 (9)	−0.1132 (4)	0.0836 (11)
H11A	0.4928	0.2614	−0.1997	0.100*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0488 (13)	0.189 (3)	0.149 (3)	−0.0310 (16)	0.0098 (15)	−0.081 (3)
O2	0.0445 (12)	0.132 (2)	0.124 (2)	0.0104 (13)	0.0155 (14)	−0.0123 (19)
O3	0.0518 (11)	0.0674 (13)	0.1045 (17)	−0.0173 (10)	0.0150 (11)	−0.0302 (14)
N1	0.0351 (10)	0.0671 (14)	0.0659 (14)	−0.0009 (10)	0.0054 (11)	−0.0012 (12)
N2	0.0611 (17)	0.131 (3)	0.088 (2)	−0.0280 (17)	0.0174 (16)	0.016 (2)
N3	0.0463 (13)	0.140 (3)	0.0707 (18)	−0.0253 (15)	−0.0077 (13)	0.0202 (19)
N4	0.0398 (13)	0.097 (2)	0.0767 (18)	−0.0046 (13)	0.0086 (12)	−0.0019 (16)
C1	0.0426 (13)	0.0573 (15)	0.0552 (15)	−0.0076 (11)	0.0018 (12)	−0.0040 (13)
C2	0.0400 (13)	0.0659 (17)	0.0568 (15)	−0.0033 (12)	0.0049 (12)	0.0071 (15)
C3	0.0564 (17)	0.0686 (18)	0.0603 (16)	0.0035 (14)	0.0144 (14)	−0.0016 (16)
C4	0.0627 (17)	0.077 (2)	0.0663 (18)	−0.0093 (16)	0.0069 (16)	−0.0196 (18)
C5	0.0429 (13)	0.0683 (17)	0.0616 (17)	−0.0108 (13)	−0.0005 (12)	−0.0028 (15)
C6	0.0410 (12)	0.0489 (14)	0.0519 (14)	−0.0045 (10)	0.0021 (11)	0.0035 (12)
C7	0.0420 (13)	0.0447 (14)	0.0620 (15)	−0.0069 (11)	−0.0014 (12)	−0.0008 (14)
C8	0.0386 (13)	0.0551 (15)	0.0672 (17)	−0.0029 (10)	0.0054 (13)	−0.0059 (15)
C9	0.0401 (13)	0.0573 (16)	0.086 (2)	−0.0057 (12)	0.0073 (14)	−0.0093 (16)
C10	0.0443 (17)	0.129 (3)	0.092 (3)	−0.0232 (18)	0.0006 (17)	0.003 (3)
C11	0.0599 (19)	0.132 (3)	0.0585 (18)	−0.017 (2)	0.0111 (16)	0.001 (2)

Geometric parameters (Å, º)

O1—N4	1.204 (4)	C3—H3B	0.9300
O2—N4	1.210 (4)	C4—C5	1.375 (4)
O3—C7	1.217 (3)	C4—H4A	0.9300
N1—C11	1.310 (4)	C5—C6	1.394 (4)
N1—N3	1.351 (4)	C5—H5A	0.9300
N1—C9	1.458 (3)	C6—C7	1.495 (4)
N2—C11	1.309 (5)	C7—C8	1.491 (3)
N2—C10	1.327 (5)	C8—C9	1.509 (4)
N3—C10	1.317 (4)	C8—H8A	0.9700
N4—C2	1.474 (4)	C8—H8B	0.9700
C1—C2	1.373 (3)	C9—H9A	0.9700
C1—C6	1.389 (3)	C9—H9B	0.9700
C1—H1A	0.9300	C10—H10A	0.9300
C2—C3	1.374 (4)	C11—H11A	0.9300
C3—C4	1.387 (4)
C11—N1—N3	109.0 (2)	C1—C6—C7	118.3 (2)
C11—N1—C9	130.3 (3)	C5—C6—C7	123.1 (2)
N3—N1—C9	120.6 (3)	O3—C7—C8	121.1 (3)
C11—N2—C10	101.8 (3)	O3—C7—C6	120.1 (2)
C10—N3—N1	101.7 (3)	C8—C7—C6	118.8 (2)
O2—N4—O1	123.7 (3)	C7—C8—C9	113.3 (2)
O2—N4—C2	118.3 (3)	C7—C8—H8A	108.9
O1—N4—C2	118.0 (3)	C9—C8—H8A	108.9
C2—C1—C6	119.3 (2)	C7—C8—H8B	108.9
C2—C1—H1A	120.3	C9—C8—H8B	108.9
C6—C1—H1A	120.3	H8A—C8—H8B	107.7
C3—C2—C1	122.7 (2)	N1—C9—C8	111.4 (2)
C3—C2—N4	118.8 (2)	N1—C9—H9A	109.4
C1—C2—N4	118.5 (3)	C8—C9—H9A	109.4
C2—C3—C4	117.9 (3)	N1—C9—H9B	109.4
C2—C3—H3B	121.0	C8—C9—H9B	109.4
C4—C3—H3B	121.0	H9A—C9—H9B	108.0
C5—C4—C3	120.5 (3)	N3—C10—N2	115.6 (3)
C5—C4—H4A	119.8	N3—C10—H10A	122.2
C3—C4—H4A	119.8	N2—C10—H10A	122.2
C4—C5—C6	120.9 (3)	N2—C11—N1	111.8 (3)
C4—C5—H5A	119.5	N2—C11—H11A	124.1
C6—C5—H5A	119.5	N1—C11—H11A	124.1
C1—C6—C5	118.6 (2)
C11—N1—N3—C10	−0.8 (4)	C4—C5—C6—C7	178.3 (3)
C9—N1—N3—C10	−178.7 (3)	C1—C6—C7—O3	−15.7 (4)
C6—C1—C2—C3	−1.5 (4)	C5—C6—C7—O3	166.3 (3)
C6—C1—C2—N4	177.8 (3)	C1—C6—C7—C8	161.6 (3)
O2—N4—C2—C3	7.3 (4)	C5—C6—C7—C8	−16.4 (4)
O1—N4—C2—C3	−172.8 (3)	O3—C7—C8—C9	−2.6 (4)
O2—N4—C2—C1	−172.0 (3)	C6—C7—C8—C9	−179.9 (2)
O1—N4—C2—C1	7.9 (4)	C11—N1—C9—C8	−113.3 (4)
C1—C2—C3—C4	−0.4 (4)	N3—N1—C9—C8	64.1 (4)
N4—C2—C3—C4	−179.7 (3)	C7—C8—C9—N1	171.1 (3)
C2—C3—C4—C5	2.4 (5)	N1—N3—C10—N2	0.3 (5)
C3—C4—C5—C6	−2.4 (5)	C11—N2—C10—N3	0.3 (5)
C2—C1—C6—C5	1.5 (4)	C10—N2—C11—N1	−0.8 (5)
C2—C1—C6—C7	−176.5 (2)	N3—N1—C11—N2	1.1 (4)
C4—C5—C6—C1	0.4 (4)	C9—N1—C11—N2	178.7 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3B···O3^i	0.93	2.48	3.400 (4)	172
C4—H4A···O1^i	0.93	2.55	3.481 (5)	175
C5—H5A···N2^ii	0.93	2.53	3.449 (4)	169

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