3-(Benzotriazol-1-yl)-p-nitro­propio­phenone: sheets built from weak three-centred C—H...O hydrogen bonds

Molecules of the title compound, C₁₅H₁₂N₄O₃, are hydrogen bonded into undulating sheets lying perpendicular to the b axis by three-centred weak C—H...O hydrogen bonds involving the O atoms of the nitro group in mol­ecules related by the c-axis glide plane.

Key indicators

• Single-crystal X-ray study
• T = 120 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.058
• wR factor = 0.155
• Data-to-parameter ratio = 14.3

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry

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Computing details

Data collection: KappaCCD Server Software (Nonius, 1997); cell refinement: DENZO–SMN (Otwinowski & Minor, 1997); data reduction: DENZO–SMN; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPII (Johnson, 1976) and PLATON (Spek, 2002); software used to prepare material for publication: SHELXL97 and WORDPERFECT macro PRPKAPPA (Ferguson, 1999).

3-(Benzotriazol-1-yl)-p-nitropropiophenone

Crystal data

C15H12N4O3	F(000) = 616
Mr = 296.29	Dx = 1.501 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 5.9554 (2) Å	Cell parameters from 2852 reflections
b = 6.9671 (3) Å	θ = 3.0–27.5°
c = 31.8248 (13) Å	µ = 0.11 mm^−1
β = 96.8560 (17)°	T = 120 K
V = 1311.03 (9) Å^3	Prism, orange
Z = 4	0.50 × 0.35 × 0.08 mm

Data collection

Nonius KappaCCD diffractometer	2852 independent reflections
Radiation source: fine-focus sealed X-ray tube	1820 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.093
φ scans and ω scans with κ offsets	θmax = 27.5°, θmin = 3.0°
Absorption correction: multi-scan (DENZO-SMN; Otwinowski & Minor, 1997)	h = −7→5
Tmin = 0.927, Tmax = 0.991	k = −9→8
6931 measured reflections	l = −40→41

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)] = 0.058	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.155	H-atom parameters constrained
S = 1.00	w = 1/[σ^2(Fo^2) + (0.079P)^2] where P = (Fo^2 + 2Fc^2)/3
2852 reflections	(Δ/σ)max < 0.001
199 parameters	Δρmax = 0.29 e Å^−3
0 restraints	Δρmin = −0.33 e Å^−3

Special details

Experimental. The program DENZO-SMN (Otwinowski & Minor, 1997) uses a scaling algorithm (Fox, G·C. & Holmes, K·C., 1966, Acta Cryst. 20, 886–891) which effectively corrects for absorption effects. High redundancy data were used in the scaling program hence the 'multi-scan' code word was used. No transmission coefficients are available from the program (only scale factors for each frame). The scale factors in the experimental table are calculated from the 'size' command in the SHELXL97 input file.

Geometry. Mean-plane data from the final SHELXL97 (Sheldrick, 1997) refinement run.

Cg1 and Cg2 are the centroids of theC3A/C4/C5/C6/C7/C7A and C11/C12/C13/C14/C15/C16 rings, respectively.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
N1	0.3867 (3)	0.0255 (3)	0.30503 (5)	0.0221 (4)
N2	0.5877 (3)	0.0778 (3)	0.29285 (5)	0.0262 (5)
C1	0.2013 (4)	−0.0410 (3)	0.27379 (6)	0.0244 (5)
C2	0.2318 (4)	0.0403 (3)	0.23038 (6)	0.0227 (5)
C3	0.0328 (4)	−0.0047 (3)	0.19785 (6)	0.0212 (5)
O3	−0.1408 (3)	−0.0761 (2)	0.20713 (4)	0.0282 (4)
N3	0.7214 (3)	0.1381 (3)	0.32595 (5)	0.0259 (5)
C3A	0.6024 (4)	0.1241 (3)	0.36072 (6)	0.0207 (5)
C4	0.6692 (4)	0.1706 (3)	0.40345 (6)	0.0235 (5)
C5	0.5134 (4)	0.1383 (3)	0.43113 (6)	0.0243 (5)
C6	0.2988 (4)	0.0628 (3)	0.41780 (6)	0.0230 (5)
C7	0.2296 (4)	0.0174 (3)	0.37601 (6)	0.0217 (5)
C7A	0.3885 (4)	0.0518 (3)	0.34777 (6)	0.0199 (5)
C11	0.0542 (4)	0.0508 (3)	0.15266 (6)	0.0214 (5)
C12	0.2512 (4)	0.1330 (3)	0.14131 (6)	0.0236 (5)
C13	0.2689 (4)	0.1819 (3)	0.09939 (6)	0.0240 (5)
C14	0.0853 (4)	0.1473 (3)	0.06987 (6)	0.0227 (5)
N14	0.1031 (4)	0.1998 (3)	0.02543 (5)	0.0298 (5)
O141	−0.0714 (3)	0.2151 (3)	0.00109 (5)	0.0399 (5)
O142	0.2927 (3)	0.2255 (3)	0.01534 (5)	0.0487 (6)
C15	−0.1150 (4)	0.0673 (3)	0.07984 (6)	0.0254 (5)
C16	−0.1279 (4)	0.0179 (3)	0.12167 (6)	0.0213 (5)
H1A	0.0546	0.0017	0.2822	0.029*
H1B	0.2010	−0.1830	0.2726	0.029*
H2A	0.2509	0.1813	0.2326	0.027*
H2B	0.3710	−0.0139	0.2209	0.027*
H4	0.8147	0.2217	0.4126	0.028*
H5	0.5523	0.1680	0.4602	0.029*
H6	0.1972	0.0422	0.4382	0.028*
H7	0.0839	−0.0338	0.3670	0.026*
H12	0.3751	0.1562	0.1624	0.028*
H13	0.4034	0.2373	0.0915	0.029*
H15	−0.2393	0.0471	0.0587	0.031*
H16	−0.2622	−0.0390	0.1293	0.026*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N1	0.0226 (11)	0.0313 (11)	0.0121 (8)	−0.0016 (9)	0.0014 (7)	0.0009 (7)
N2	0.0244 (10)	0.0370 (12)	0.0170 (9)	−0.0033 (9)	0.0012 (8)	0.0016 (8)
C1	0.0259 (13)	0.0330 (13)	0.0130 (10)	−0.0038 (11)	−0.0038 (9)	−0.0015 (9)
C2	0.0281 (13)	0.0268 (12)	0.0130 (10)	0.0021 (10)	0.0021 (9)	0.0028 (9)
C3	0.0253 (13)	0.0217 (12)	0.0166 (10)	0.0010 (10)	0.0023 (9)	−0.0023 (9)
O3	0.0302 (10)	0.0363 (10)	0.0179 (8)	−0.0049 (8)	0.0024 (7)	−0.0011 (7)
N3	0.0244 (11)	0.0372 (12)	0.0156 (9)	−0.0043 (9)	0.0006 (8)	−0.0006 (8)
C3A	0.0224 (12)	0.0252 (12)	0.0143 (10)	−0.0007 (10)	0.0010 (8)	0.0002 (8)
C4	0.0234 (13)	0.0287 (13)	0.0169 (10)	−0.0033 (10)	−0.0034 (9)	−0.0010 (9)
C5	0.0295 (13)	0.0271 (13)	0.0150 (10)	0.0021 (11)	−0.0023 (9)	−0.0032 (9)
C6	0.0260 (13)	0.0299 (13)	0.0137 (10)	0.0006 (10)	0.0045 (9)	0.0004 (9)
C7	0.0224 (13)	0.0259 (13)	0.0160 (10)	−0.0013 (10)	−0.0006 (8)	0.0015 (9)
C7A	0.0260 (13)	0.0214 (12)	0.0115 (9)	0.0023 (10)	−0.0011 (8)	0.0002 (8)
C11	0.0266 (13)	0.0224 (12)	0.0148 (10)	0.0022 (10)	0.0006 (9)	−0.0006 (9)
C12	0.0279 (13)	0.0287 (13)	0.0132 (10)	−0.0017 (11)	−0.0020 (9)	−0.0016 (9)
C13	0.0286 (13)	0.0259 (13)	0.0179 (11)	−0.0025 (10)	0.0049 (9)	−0.0002 (9)
C14	0.0314 (13)	0.0257 (12)	0.0111 (10)	0.0047 (10)	0.0029 (9)	0.0018 (9)
N14	0.0390 (13)	0.0345 (12)	0.0157 (9)	−0.0024 (10)	0.0019 (9)	0.0011 (8)
O141	0.0458 (12)	0.0546 (12)	0.0174 (8)	0.0088 (10)	−0.0042 (8)	0.0064 (8)
O142	0.0507 (12)	0.0774 (15)	0.0189 (8)	−0.0183 (11)	0.0084 (8)	0.0039 (9)
C15	0.0309 (14)	0.0291 (13)	0.0148 (10)	0.0031 (11)	−0.0037 (9)	−0.0033 (9)
C16	0.0211 (13)	0.0243 (12)	0.0183 (10)	−0.0011 (10)	0.0016 (9)	−0.0006 (9)

Geometric parameters (Å, º)

N1—N2	1.351 (2)	C5—H5	0.950
N1—C7A	1.371 (2)	C6—C7	1.381 (3)
N1—C1	1.469 (2)	C6—H6	0.950
N2—N3	1.312 (2)	C7—C7A	1.402 (3)
C1—C2	1.524 (3)	C7—H7	0.950
C1—H1A	0.990	C11—C12	1.392 (3)
C1—H1B	0.990	C11—C16	1.395 (3)
C2—C3	1.511 (3)	C12—C13	1.393 (3)
C2—H2A	0.990	C12—H12	0.950
C2—H2B	0.990	C13—C14	1.375 (3)
C3—O3	1.215 (3)	C13—H13	0.950
C3—C11	1.509 (3)	C14—C15	1.387 (3)
N3—C3A	1.387 (3)	C14—N14	1.477 (2)
C3A—C7A	1.386 (3)	N14—O142	1.223 (3)
C3A—C4	1.408 (3)	N14—O141	1.224 (2)
C4—C5	1.372 (3)	C15—C16	1.386 (3)
C4—H4	0.950	C15—H15	0.950
C5—C6	1.400 (3)	C16—H16	0.950
N2—N1—C7A	110.24 (17)	C7—C6—H6	118.8
N2—N1—C1	120.71 (16)	C5—C6—H6	118.8
C7A—N1—C1	129.01 (18)	C6—C7—C7A	115.6 (2)
N3—N2—N1	109.27 (16)	C6—C7—H7	122.2
N1—C1—C2	109.55 (18)	C7A—C7—H7	122.2
N1—C1—H1A	109.8	N1—C7A—C3A	104.00 (18)
C2—C1—H1A	109.8	N1—C7A—C7	133.4 (2)
N1—C1—H1B	109.8	C3A—C7A—C7	122.57 (18)
C2—C1—H1B	109.8	C12—C11—C16	119.52 (18)
H1A—C1—H1B	108.2	C12—C11—C3	121.49 (18)
C3—C2—C1	112.06 (19)	C16—C11—C3	118.99 (19)
C3—C2—H2A	109.2	C11—C12—C13	120.77 (19)
C1—C2—H2A	109.2	C11—C12—H12	119.6
C3—C2—H2B	109.2	C13—C12—H12	119.6
C1—C2—H2B	109.2	C14—C13—C12	117.8 (2)
H2A—C2—H2B	107.9	C14—C13—H13	121.1
O3—C3—C11	120.50 (19)	C12—C13—H13	121.1
O3—C3—C2	122.61 (18)	C13—C14—C15	123.33 (19)
C11—C3—C2	116.85 (19)	C13—C14—N14	118.0 (2)
N2—N3—C3A	107.38 (18)	C15—C14—N14	118.70 (19)
C7A—C3A—N3	109.11 (18)	O142—N14—O141	124.16 (19)
C7A—C3A—C4	121.0 (2)	O142—N14—C14	117.47 (19)
N3—C3A—C4	129.9 (2)	O141—N14—C14	118.36 (19)
C5—C4—C3A	116.6 (2)	C16—C15—C14	117.86 (19)
C5—C4—H4	121.7	C16—C15—H15	121.1
C3A—C4—H4	121.7	C14—C15—H15	121.1
C4—C5—C6	121.98 (19)	C15—C16—C11	120.7 (2)
C4—C5—H5	119.0	C15—C16—H16	119.7
C6—C5—H5	119.0	C11—C16—H16	119.7
C7—C6—C5	122.3 (2)
C7A—N1—N2—N3	−0.2 (2)	C4—C3A—C7A—C7	−1.2 (3)
C1—N1—N2—N3	177.64 (19)	C6—C7—C7A—N1	179.4 (2)
N2—N1—C1—C2	−24.6 (3)	C6—C7—C7A—C3A	0.8 (3)
C7A—N1—C1—C2	152.8 (2)	O3—C3—C11—C12	179.9 (2)
N1—C1—C2—C3	−173.63 (17)	C2—C3—C11—C12	2.3 (3)
C1—C2—C3—O3	8.6 (3)	O3—C3—C11—C16	−0.4 (3)
C1—C2—C3—C11	−173.89 (19)	C2—C3—C11—C16	−177.93 (19)
N1—N2—N3—C3A	0.0 (2)	C16—C11—C12—C13	−0.3 (3)
N2—N3—C3A—C7A	0.2 (3)	C3—C11—C12—C13	179.4 (2)
N2—N3—C3A—C4	−180.0 (2)	C11—C12—C13—C14	0.4 (3)
C7A—C3A—C4—C5	0.7 (3)	C12—C13—C14—C15	0.2 (4)
N3—C3A—C4—C5	−179.1 (2)	C12—C13—C14—N14	179.70 (19)
C3A—C4—C5—C6	0.1 (3)	C13—C14—N14—O142	17.8 (3)
C4—C5—C6—C7	−0.4 (4)	C15—C14—N14—O142	−162.7 (2)
C5—C6—C7—C7A	0.0 (3)	C13—C14—N14—O141	−162.2 (2)
N2—N1—C7A—C3A	0.3 (2)	C15—C14—N14—O141	17.4 (3)
C1—N1—C7A—C3A	−177.3 (2)	C13—C14—C15—C16	−0.9 (4)
N2—N1—C7A—C7	−178.5 (2)	N14—C14—C15—C16	179.60 (19)
C1—N1—C7A—C7	3.9 (4)	C14—C15—C16—C11	1.0 (3)
N3—C3A—C7A—N1	−0.3 (2)	C12—C11—C16—C15	−0.4 (3)
C4—C3A—C7A—N1	179.8 (2)	C3—C11—C16—C15	179.8 (2)
N3—C3A—C7A—C7	178.6 (2)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C5—H5···O141^i	0.95	2.59	3.286 (3)	131
C5—H5···O142^ii	0.95	2.58	3.264 (3)	129
C4—H4···Cg2^iii	0.95	2.84	3.425 (2)	121
C7—H7···Cg2^iv	0.95	2.83	3.464 (2)	125
C13—H13···Cg1^iii	0.95	2.68	3.321 (2)	125
C16—H16···Cg1^iv	0.95	2.83	3.516 (2)	130

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