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

In the title mol­ecule, C₁₁H₁₀N₄O₃, the dihedral angle between the benzene and triazole rings is 60.4 (1)°. Weak inter­molecular C–H...O hydrogen bonds and van der Waals forces stabilize the crystal packing.

Key indicators

• Single-crystal X-ray study
• T = 294 K
• Mean [sigma](C-C) = 0.002 Å
• R factor = 0.041
• wR factor = 0.116
• Data-to-parameter ratio = 12.8

checkCIF/PLATON results

No syntax errors found





Alert level C
PLAT041_ALERT_1_C Calc. and Rep. SumFormula Strings    Differ ....          ?
PLAT045_ALERT_1_C Calculated and Reported Z Differ by ............       4.00 Ratio
PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given .......          ?
PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd.  #          1
              C11 H10 N4 O3

Alert level G
FORMU01_ALERT_1_G  There is a discrepancy between the atom counts in the
            _chemical_formula_sum and _chemical_formula_moiety. This is
            usually due to the moiety formula being in the wrong format.
            Atom count from _chemical_formula_sum:   C44 H40 N16 O12
            Atom count from _chemical_formula_moiety:C11 H10 N4 O3

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   4 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
   0 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
   2 ALERT type 4 Improvement, methodology, query or suggestion

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S1. Comment

In our ongoing studies of triazole compounds, the title compound, (I), was obtained by the reaction of triazole and 3-(dimethylamino)-1-(4-nitrophenyl)-propan-1-one hydrochloride. An X-ray crystallographic analysis was undertaken to establish its structure.

The bond lengths and angles in (I) (Table 1) are within normal ranges (Allen et al., 1987) and comparable with those in the related compounds (Wan, Li, Li, Li et al., 2005; Wan, Li, Li, Wang et al., 2005). The molecule of (I) is non-planar; the benzene and triazole rings make a dihedral angle of 60.4 (1)°. In the crystal, weak intermolecular C—H···O hydrogen bonds (Table 2) link the molecules into the ribbons. The crystal packing (Table 2) is further stabilized by van der Waals forces.

S2. Experimental

To a solution of 3-(dimethylamino)-1-(4-nitrophenyl)propan-1-one hydrochloride (18 g, 0.07 mol) in water (20 ml) was added triazole (5.5 g, 0.08 mol). The mixture was heated under reflux for 5 h, yielding a copious precipitate. Colourless single crystals suitable for X-ray diffraction study were obtained by slow evaporation of an ethyl acetate-petroleum ether solution (2:1,(v/v) over a period of 10 d.

S3. Refinement

All H atoms were located in a difference Fourier map and constrained to ride on their parent atoms, with C—H distances in the range 0.93–0.97 Å and U_iso(H) = 1.2 U_eq(C).

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: SHELXTL; software used to prepare material for publication: SHELXTL, PARST (Nardelli, 1995) and PLATON (Spek, 2003).

Figures

	Fig. 1. View of (I), showing the atom numbering scheme and 50% probability displacement ellipsoids.
	Fig. 2. The crystal packing, viewed down the b axis. The intermolecular C—H···O hydrogen bonds are indicated by dashed lines.

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

Crystal data

C11H10N4O3	F(000) = 512
Mr = 246.23	Dx = 1.441 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 9.8529 (7) Å	Cell parameters from 2976 reflections
b = 5.4011 (4) Å	θ = 2.5–26.0°
c = 21.9132 (14) Å	µ = 0.11 mm^−1
β = 103.233 (3)°	T = 294 K
V = 1135.18 (14) Å^3	Plate, colourless
Z = 4	0.49 × 0.35 × 0.11 mm

Data collection

Simens SMART 1000 CCD area detector diffractometer	2231 independent reflections
Radiation source: fine-focus sealed tube	1956 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.015
Detector resolution: 8.33 pixels mm^-1	θmax = 26.0°, θmin = 1.9°
ω scans	h = −11→12
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	k = −6→6
Tmin = 0.943, Tmax = 0.984	l = −22→27
6034 measured reflections

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.041	All H-atom parameters refined
wR(F^2) = 0.116	w = 1/[σ^2(Fo^2) + (0.0627P)^2 + 0.1874P] where P = (Fo^2 + 2Fc^2)/3
S = 1.03	(Δ/σ)max < 0.001
2231 reflections	Δρmax = 0.17 e Å^−3
174 parameters	Δρmin = −0.19 e Å^−3
0 restraints	Extinction correction: SHELXL, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.030 (4)

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	0.89452 (12)	−0.2351 (3)	0.02312 (7)	0.1040 (5)
O2	0.70365 (13)	−0.0889 (3)	0.03977 (6)	0.0834 (4)
O3	0.52640 (11)	−1.0409 (2)	−0.19541 (6)	0.0763 (4)
N1	0.76753 (13)	−0.2293 (3)	0.01285 (6)	0.0669 (4)
N2	0.12801 (11)	−0.9109 (2)	−0.30104 (5)	0.0517 (3)
N3	0.09999 (13)	−0.6937 (3)	−0.33185 (7)	0.0690 (4)
N4	−0.09294 (14)	−0.9264 (3)	−0.34626 (8)	0.0811 (5)
C1	0.68188 (14)	−0.7488 (3)	−0.10050 (7)	0.0564 (4)
H1A	0.7258	−0.8828	−0.1144	0.063 (4)*
C2	0.75692 (14)	−0.5941 (3)	−0.05504 (7)	0.0595 (4)
H2A	0.8514	−0.6207	−0.0385	0.071 (5)*
C3	0.68863 (14)	−0.3993 (3)	−0.03473 (6)	0.0548 (4)
C4	0.54824 (14)	−0.3547 (3)	−0.05758 (7)	0.0553 (4)
H4B	0.5043	−0.2239	−0.0423	0.066 (4)*
C5	0.47466 (13)	−0.5088 (3)	−0.10371 (6)	0.0520 (3)
H5A	0.3803	−0.4804	−0.1202	0.059 (4)*
C6	0.54032 (13)	−0.7058 (3)	−0.12578 (6)	0.0479 (3)
C7	0.46646 (13)	−0.8693 (3)	−0.17789 (6)	0.0506 (3)
C8	0.31662 (13)	−0.8150 (3)	−0.20892 (6)	0.0535 (4)
H8A	0.2584	−0.8475	−0.1796	0.068 (5)*
H8B	0.3070	−0.6414	−0.2205	0.073 (5)*
C9	0.26867 (14)	−0.9722 (3)	−0.26654 (7)	0.0590 (4)
H9A	0.3325	−0.9505	−0.2939	0.078 (5)*
H9B	0.2715	−1.1450	−0.2543	0.075 (5)*
C10	0.01315 (16)	−1.0436 (3)	−0.31051 (8)	0.0714 (5)
H10A	0.0076	−1.2009	−0.2940	0.091 (6)*
C11	−0.03301 (16)	−0.7159 (3)	−0.35809 (8)	0.0707 (5)
H11A	−0.0825	−0.5926	−0.3834	0.097 (6)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0535 (7)	0.1390 (13)	0.1094 (11)	−0.0130 (8)	−0.0024 (7)	−0.0372 (10)
O2	0.0751 (8)	0.0908 (9)	0.0799 (8)	−0.0060 (7)	0.0090 (6)	−0.0226 (7)
O3	0.0602 (6)	0.0731 (7)	0.0869 (8)	0.0225 (6)	−0.0012 (5)	−0.0157 (6)
N1	0.0576 (8)	0.0789 (9)	0.0590 (7)	−0.0087 (7)	0.0025 (6)	0.0014 (7)
N2	0.0465 (6)	0.0490 (6)	0.0562 (7)	−0.0018 (5)	0.0050 (5)	−0.0005 (5)
N3	0.0562 (7)	0.0634 (8)	0.0806 (9)	−0.0065 (6)	0.0016 (6)	0.0171 (7)
N4	0.0533 (7)	0.0877 (11)	0.0908 (10)	−0.0159 (7)	−0.0070 (7)	0.0108 (8)
C1	0.0454 (7)	0.0646 (9)	0.0572 (8)	0.0091 (6)	0.0078 (6)	0.0071 (7)
C2	0.0408 (7)	0.0758 (10)	0.0579 (8)	0.0036 (7)	0.0032 (6)	0.0089 (7)
C3	0.0499 (7)	0.0640 (9)	0.0482 (7)	−0.0061 (6)	0.0063 (6)	0.0073 (6)
C4	0.0491 (7)	0.0619 (9)	0.0540 (8)	0.0024 (6)	0.0101 (6)	0.0014 (6)
C5	0.0401 (6)	0.0610 (8)	0.0531 (7)	0.0032 (6)	0.0071 (5)	0.0056 (6)
C6	0.0421 (7)	0.0541 (8)	0.0470 (7)	0.0033 (5)	0.0092 (5)	0.0102 (6)
C7	0.0455 (7)	0.0524 (8)	0.0537 (7)	0.0066 (6)	0.0106 (6)	0.0077 (6)
C8	0.0434 (7)	0.0614 (9)	0.0540 (8)	0.0055 (6)	0.0076 (6)	−0.0024 (6)
C9	0.0497 (8)	0.0568 (9)	0.0659 (9)	0.0064 (6)	0.0039 (6)	−0.0067 (7)
C10	0.0613 (9)	0.0623 (10)	0.0826 (11)	−0.0169 (8)	0.0000 (8)	0.0075 (8)
C11	0.0577 (9)	0.0764 (11)	0.0694 (10)	0.0013 (8)	−0.0033 (7)	0.0137 (8)

Geometric parameters (Å, º)

O1—N1	1.2200 (16)	C3—C4	1.3803 (19)
O2—N1	1.2201 (18)	C4—C5	1.380 (2)
O3—C7	1.2077 (17)	C4—H4B	0.9300
N1—C3	1.471 (2)	C5—C6	1.3886 (19)
N2—C10	1.3153 (18)	C5—H5A	0.9300
N2—N3	1.3499 (17)	C6—C7	1.494 (2)
N2—C9	1.4568 (17)	C7—C8	1.5062 (18)
N3—C11	1.3104 (19)	C8—C9	1.505 (2)
N4—C10	1.316 (2)	C8—H8A	0.9700
N4—C11	1.334 (2)	C8—H8B	0.9700
C1—C2	1.378 (2)	C9—H9A	0.9701
C1—C6	1.3973 (18)	C9—H9B	0.9699
C1—H1A	0.9299	C10—H10A	0.9300
C2—C3	1.376 (2)	C11—H11A	0.9300
C2—H2A	0.9300
O2—N1—O1	123.21 (15)	C5—C6—C7	122.34 (11)
O2—N1—C3	118.90 (13)	C1—C6—C7	118.15 (12)
O1—N1—C3	117.89 (15)	O3—C7—C6	120.56 (12)
C10—N2—N3	108.93 (12)	O3—C7—C8	120.40 (13)
C10—N2—C9	129.78 (13)	C6—C7—C8	119.03 (12)
N3—N2—C9	121.23 (12)	C9—C8—C7	110.85 (11)
C11—N3—N2	102.09 (12)	C9—C8—H8A	109.5
C10—N4—C11	101.48 (13)	C7—C8—H8A	109.5
C2—C1—C6	120.48 (14)	C9—C8—H8B	109.5
C2—C1—H1A	119.8	C7—C8—H8B	109.5
C6—C1—H1A	119.8	H8A—C8—H8B	108.1
C3—C2—C1	118.42 (13)	N2—C9—C8	112.69 (11)
C3—C2—H2A	120.8	N2—C9—H9A	109.0
C1—C2—H2A	120.8	C8—C9—H9A	109.1
C2—C3—C4	122.67 (14)	N2—C9—H9B	109.1
C2—C3—N1	119.23 (13)	C8—C9—H9B	109.1
C4—C3—N1	118.10 (14)	H9A—C9—H9B	107.8
C5—C4—C3	118.37 (14)	N2—C10—N4	111.67 (15)
C5—C4—H4B	120.8	N2—C10—H10A	124.2
C3—C4—H4B	120.8	N4—C10—H10A	124.2
C4—C5—C6	120.58 (12)	N3—C11—N4	115.82 (15)
C4—C5—H5A	119.7	N3—C11—H11A	122.1
C6—C5—H5A	119.7	N4—C11—H11A	122.1
C5—C6—C1	119.46 (13)
C10—N2—N3—C11	−0.23 (18)	C2—C1—C6—C7	176.02 (13)
C9—N2—N3—C11	177.40 (13)	C5—C6—C7—O3	−179.13 (13)
C6—C1—C2—C3	0.9 (2)	C1—C6—C7—O3	3.5 (2)
C1—C2—C3—C4	0.7 (2)	C5—C6—C7—C8	1.75 (19)
C1—C2—C3—N1	−178.79 (13)	C1—C6—C7—C8	−175.67 (12)
O2—N1—C3—C2	−165.50 (14)	O3—C7—C8—C9	−8.5 (2)
O1—N1—C3—C2	14.9 (2)	C6—C7—C8—C9	170.63 (12)
O2—N1—C3—C4	15.0 (2)	C10—N2—C9—C8	−113.84 (18)
O1—N1—C3—C4	−164.54 (15)	N3—N2—C9—C8	69.08 (18)
C2—C3—C4—C5	−1.6 (2)	C7—C8—C9—N2	−175.10 (12)
N1—C3—C4—C5	177.91 (13)	N3—N2—C10—N4	−0.3 (2)
C3—C4—C5—C6	0.9 (2)	C9—N2—C10—N4	−177.70 (15)
C4—C5—C6—C1	0.6 (2)	C11—N4—C10—N2	0.7 (2)
C4—C5—C6—C7	−176.82 (12)	N2—N3—C11—N4	0.7 (2)
C2—C1—C6—C5	−1.5 (2)	C10—N4—C11—N3	−0.9 (2)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2A···O1^i	0.93	2.57	3.469 (2)	163
C11—H11A···O2^ii	0.93	2.57	3.435 (2)	154

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