5-Nitro-1-(prop-2-yn-1-yl)-2,3-dihydro-1H-1,3-benzodiazol-2-one.

In the two independent mol-ecules of the title compound, C(10)H(7)N(3)O(3), the nitro substitutent is twisted slightly with respect to the benzodiazol fused-ring system [dihedral angles = 4.9 (3) and 8.5 (1)°]. The two independent mol-ecules are disposed about a pseudo inversion center and are held together by N-H⋯O hydrogen bonds. The supramolecular dimer is essentially planar [dihedral angle between the fused rings = 2.0 (1)°]. Adjacent dimers are linked by acetyl-ene-nitro C-H⋯O inter-actions, generating a ribbon motif along (110).

Related literature

For related structures, see: Ouzidan et al. (2011a ▶,b ▶,c ▶).

Experimental

Crystal data

C10H7N3O3

M = 217.19

Triclinic,

a = 7.2541 (2) Å

b = 10.0362 (2) Å

c = 14.6793 (3) Å

α = 100.978 (1)°

β = 92.047 (1)°

γ = 109.043 (1)°

V = 986.20 (4) Å3

Z = 4

Mo Kα radiation

μ = 0.11 mm−1

T = 293 K

0.27 × 0.22 × 0.13 mm

Data collection

Bruker APEX DUO diffractometer

20686 measured reflections

4506 independent reflections

2855 reflections with I > 2σ(I)

R int = 0.032

Refinement

R[F 2 > 2σ(F 2)] = 0.045

wR(F 2) = 0.158

S = 1.05

4506 reflections

305 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.20 e Å−3

Δρmin = −0.24 e Å−3

Data collection: APEX2 (Bruker, 2010 ▶); cell refinement: SAINT (Bruker, 2010 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: X-SEED (Barbour, 2001 ▶); software used to prepare material for publication: publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812013177/bt5859sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812013177/bt5859Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812013177/bt5859Isup3.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C10H7N3O3	Z = 4
Mr = 217.19	F(000) = 448
Triclinic, P1	Dx = 1.463 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.2541 (2) Å	Cell parameters from 5674 reflections
b = 10.0362 (2) Å	θ = 2.2–28.0°
c = 14.6793 (3) Å	µ = 0.11 mm−1
α = 100.978 (1)°	T = 293 K
β = 92.047 (1)°	Prism, yellow
γ = 109.043 (1)°	0.27 × 0.22 × 0.13 mm
V = 986.20 (4) Å3

Bruker APEX DUO diffractometer	2855 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.032
Graphite monochromator	θmax = 27.5°, θmin = 2.2°
ω scans	h = −9→9
20686 measured reflections	k = −13→12
4506 independent reflections	l = −19→19

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.045	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.158	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	w = 1/[σ2(Fo2) + (0.0746P)2 + 0.2589P] where P = (Fo2 + 2Fc2)/3
4506 reflections	(Δ/σ)max = 0.001
305 parameters	Δρmax = 0.20 e Å−3
0 restraints	Δρmin = −0.24 e Å−3

	x	y	z	Uiso*/Ueq
O1	0.4863 (2)	0.28214 (16)	0.32061 (10)	0.0583 (4)
O2	0.2729 (3)	0.70175 (19)	−0.06407 (12)	0.0780 (5)
O3	0.4106 (3)	0.84006 (18)	0.06741 (13)	0.0826 (6)
O4	0.7053 (2)	0.67457 (15)	0.41638 (10)	0.0556 (4)
O5	1.0136 (4)	0.2778 (2)	0.79280 (13)	0.1056 (8)
O6	0.8109 (3)	0.13338 (17)	0.67890 (13)	0.0826 (6)
N1	0.4993 (2)	0.47954 (18)	0.25677 (11)	0.0459 (4)
N2	0.3361 (2)	0.26206 (16)	0.17380 (10)	0.0438 (4)
N3	0.3367 (2)	0.72031 (19)	0.01736 (13)	0.0535 (4)
N4	0.7143 (2)	0.48027 (17)	0.47997 (11)	0.0416 (4)
N5	0.8738 (2)	0.70106 (16)	0.55973 (10)	0.0429 (4)
N6	0.9101 (3)	0.25456 (19)	0.72058 (13)	0.0583 (5)
C1	0.4468 (3)	0.3367 (2)	0.25799 (13)	0.0447 (4)
C2	0.2539 (3)	0.1058 (2)	0.14690 (15)	0.0555 (5)
H2A	0.3007	0.0644	0.1936	0.067*
H2B	0.2988	0.0734	0.0880	0.067*
C3	0.0406 (4)	0.0549 (2)	0.13742 (15)	0.0585 (6)
C4	−0.1296 (5)	0.0194 (3)	0.1295 (2)	0.0859 (9)
C5	0.3154 (3)	0.35855 (19)	0.12192 (12)	0.0391 (4)
C6	0.2169 (3)	0.3381 (2)	0.03563 (13)	0.0450 (4)
H6	0.1471	0.2461	0.0011	0.054*
C7	0.2259 (3)	0.4598 (2)	0.00241 (13)	0.0454 (4)
H7	0.1628	0.4505	−0.0559	0.054*
C8	0.3287 (3)	0.5950 (2)	0.05579 (13)	0.0418 (4)
C9	0.4281 (3)	0.6184 (2)	0.14315 (13)	0.0428 (4)
H9	0.4961	0.7107	0.1778	0.051*
C10	0.4197 (2)	0.49734 (19)	0.17501 (12)	0.0391 (4)
C11	0.7577 (3)	0.6231 (2)	0.47796 (13)	0.0432 (4)
C12	0.9419 (3)	0.8575 (2)	0.58554 (15)	0.0552 (5)
H12A	0.8899	0.8870	0.6430	0.066*
H12B	0.8916	0.8943	0.5372	0.066*
C13	1.1548 (4)	0.9205 (2)	0.59851 (15)	0.0621 (6)
C14	1.3251 (5)	0.9698 (3)	0.6118 (2)	0.0942 (10)
C15	0.9034 (3)	0.60770 (18)	0.61264 (12)	0.0381 (4)
C16	1.0082 (3)	0.6333 (2)	0.69790 (13)	0.0452 (4)
H16	1.0756	0.7267	0.7310	0.054*
C17	1.0092 (3)	0.5145 (2)	0.73252 (13)	0.0463 (5)
H17	1.0786	0.5271	0.7898	0.056*
C18	0.9065 (3)	0.3768 (2)	0.68142 (13)	0.0432 (4)
C19	0.7999 (3)	0.34865 (19)	0.59536 (12)	0.0404 (4)
H19	0.7318	0.2552	0.5625	0.048*
C20	0.8012 (2)	0.46764 (19)	0.56177 (12)	0.0371 (4)
H1	0.574 (3)	0.554 (3)	0.3093 (17)	0.073 (7)*
H4	0.645 (3)	0.409 (2)	0.4297 (16)	0.060 (6)*
H41	−0.263 (6)	−0.002 (4)	0.122 (3)	0.138 (14)*
H141	1.454 (5)	1.011 (3)	0.621 (2)	0.118 (12)*

	U11	U22	U33	U12	U13	U23
O1	0.0683 (9)	0.0531 (9)	0.0505 (8)	0.0149 (7)	−0.0098 (7)	0.0175 (7)
O2	0.0971 (13)	0.0713 (11)	0.0680 (11)	0.0265 (10)	−0.0142 (9)	0.0289 (9)
O3	0.1019 (14)	0.0448 (10)	0.0931 (13)	0.0164 (9)	−0.0181 (10)	0.0160 (9)
O4	0.0672 (9)	0.0501 (8)	0.0493 (8)	0.0188 (7)	−0.0090 (7)	0.0151 (7)
O5	0.169 (2)	0.0641 (12)	0.0750 (12)	0.0367 (12)	−0.0557 (13)	0.0130 (10)
O6	0.1049 (14)	0.0406 (9)	0.0919 (13)	0.0138 (9)	−0.0253 (10)	0.0156 (9)
N1	0.0484 (9)	0.0429 (9)	0.0398 (9)	0.0081 (7)	−0.0054 (7)	0.0082 (7)
N2	0.0512 (9)	0.0392 (9)	0.0398 (8)	0.0157 (7)	0.0000 (7)	0.0060 (7)
N3	0.0492 (10)	0.0468 (10)	0.0649 (12)	0.0145 (8)	0.0006 (8)	0.0172 (9)
N4	0.0445 (9)	0.0383 (9)	0.0376 (8)	0.0107 (7)	−0.0035 (7)	0.0050 (7)
N5	0.0526 (9)	0.0351 (8)	0.0396 (8)	0.0146 (7)	0.0018 (7)	0.0055 (7)
N6	0.0762 (12)	0.0428 (10)	0.0556 (11)	0.0211 (9)	−0.0062 (9)	0.0104 (8)
C1	0.0451 (10)	0.0465 (11)	0.0416 (10)	0.0147 (8)	0.0014 (8)	0.0092 (9)
C2	0.0770 (15)	0.0389 (11)	0.0518 (12)	0.0243 (10)	0.0004 (10)	0.0051 (9)
C3	0.0795 (16)	0.0329 (10)	0.0503 (12)	0.0084 (10)	−0.0016 (11)	−0.0006 (9)
C4	0.082 (2)	0.0561 (16)	0.088 (2)	−0.0025 (14)	0.0001 (16)	−0.0130 (14)
C5	0.0418 (9)	0.0385 (10)	0.0380 (9)	0.0159 (8)	0.0051 (7)	0.0064 (8)
C6	0.0519 (11)	0.0399 (10)	0.0384 (10)	0.0142 (8)	−0.0013 (8)	0.0008 (8)
C7	0.0472 (10)	0.0484 (11)	0.0404 (10)	0.0175 (9)	−0.0019 (8)	0.0081 (8)
C8	0.0400 (9)	0.0437 (10)	0.0446 (10)	0.0156 (8)	0.0057 (8)	0.0131 (8)
C9	0.0402 (10)	0.0371 (10)	0.0460 (11)	0.0087 (7)	0.0039 (8)	0.0046 (8)
C10	0.0356 (9)	0.0422 (10)	0.0363 (9)	0.0106 (7)	0.0031 (7)	0.0059 (8)
C11	0.0428 (10)	0.0440 (11)	0.0422 (10)	0.0144 (8)	0.0033 (8)	0.0089 (8)
C12	0.0725 (14)	0.0361 (11)	0.0553 (12)	0.0177 (10)	0.0026 (10)	0.0076 (9)
C13	0.0790 (17)	0.0394 (11)	0.0541 (13)	0.0046 (11)	−0.0032 (11)	0.0067 (10)
C14	0.081 (2)	0.0721 (19)	0.096 (2)	−0.0106 (16)	−0.0107 (17)	0.0092 (16)
C15	0.0429 (9)	0.0350 (9)	0.0360 (9)	0.0137 (7)	0.0070 (7)	0.0054 (7)
C16	0.0537 (11)	0.0372 (10)	0.0379 (10)	0.0119 (8)	−0.0001 (8)	−0.0008 (8)
C17	0.0558 (11)	0.0465 (11)	0.0344 (9)	0.0180 (9)	−0.0018 (8)	0.0032 (8)
C18	0.0498 (10)	0.0393 (10)	0.0415 (10)	0.0173 (8)	0.0039 (8)	0.0075 (8)
C19	0.0432 (10)	0.0337 (9)	0.0401 (10)	0.0111 (7)	0.0020 (8)	0.0021 (7)
C20	0.0365 (9)	0.0399 (10)	0.0337 (9)	0.0138 (7)	0.0040 (7)	0.0036 (7)

O1—C1	1.226 (2)	C4—H41	0.92 (4)
O2—N3	1.224 (2)	C5—C6	1.377 (2)
O3—N3	1.219 (2)	C5—C10	1.406 (2)
O4—C11	1.229 (2)	C6—C7	1.382 (3)
O5—N6	1.215 (2)	C6—H6	0.9300
O6—N6	1.219 (2)	C7—C8	1.380 (3)
N1—C1	1.362 (2)	C7—H7	0.9300
N1—C10	1.380 (2)	C8—C9	1.389 (3)
N1—H1	0.96 (2)	C9—C10	1.367 (3)
N2—C5	1.381 (2)	C9—H9	0.9300
N2—C1	1.385 (2)	C12—C13	1.455 (3)
N2—C2	1.452 (2)	C12—H12A	0.9700
N3—C8	1.459 (2)	C12—H12B	0.9700
N4—C11	1.370 (2)	C13—C14	1.164 (4)
N4—C20	1.383 (2)	C14—H141	0.88 (3)
N4—H4	0.92 (2)	C15—C16	1.375 (2)
N5—C11	1.379 (2)	C15—C20	1.401 (2)
N5—C15	1.387 (2)	C16—C17	1.384 (3)
N5—C12	1.452 (2)	C16—H16	0.9300
N6—C18	1.457 (2)	C17—C18	1.387 (3)
C2—C3	1.455 (3)	C17—H17	0.9300
C2—H2A	0.9700	C18—C19	1.388 (3)
C2—H2B	0.9700	C19—C20	1.373 (2)
C3—C4	1.162 (4)	C19—H19	0.9300
C1—N1—C10	110.23 (16)	C7—C8—C9	123.72 (17)
C1—N1—H1	121.9 (14)	C7—C8—N3	118.08 (17)
C10—N1—H1	127.7 (14)	C9—C8—N3	118.18 (17)
C5—N2—C1	109.67 (15)	C10—C9—C8	115.85 (17)
C5—N2—C2	126.40 (16)	C10—C9—H9	122.1
C1—N2—C2	123.92 (16)	C8—C9—H9	122.1
O3—N3—O2	122.50 (18)	C9—C10—N1	131.69 (17)
O3—N3—C8	118.46 (18)	C9—C10—C5	121.39 (16)
O2—N3—C8	119.03 (18)	N1—C10—C5	106.92 (16)
C11—N4—C20	109.80 (15)	O4—C11—N4	127.80 (18)
C11—N4—H4	120.7 (13)	O4—C11—N5	125.54 (18)
C20—N4—H4	129.3 (14)	N4—C11—N5	106.66 (16)
C11—N5—C15	109.80 (15)	N5—C12—C13	112.49 (17)
C11—N5—C12	123.13 (16)	N5—C12—H12A	109.1
C15—N5—C12	126.98 (16)	C13—C12—H12A	109.1
O5—N6—O6	122.84 (18)	N5—C12—H12B	109.1
O5—N6—C18	118.59 (18)	C13—C12—H12B	109.1
O6—N6—C18	118.57 (17)	H12A—C12—H12B	107.8
O1—C1—N1	127.84 (18)	C14—C13—C12	177.7 (3)
O1—C1—N2	125.59 (18)	C13—C14—H141	177 (2)
N1—C1—N2	106.57 (16)	C16—C15—N5	131.48 (17)
N2—C2—C3	111.72 (17)	C16—C15—C20	122.06 (16)
N2—C2—H2A	109.3	N5—C15—C20	106.46 (15)
C3—C2—H2A	109.3	C15—C16—C17	117.40 (17)
N2—C2—H2B	109.3	C15—C16—H16	121.3
C3—C2—H2B	109.3	C17—C16—H16	121.3
H2A—C2—H2B	107.9	C16—C17—C18	119.75 (17)
C4—C3—C2	177.4 (3)	C16—C17—H17	120.1
C3—C4—H41	176 (2)	C18—C17—H17	120.1
C6—C5—N2	131.73 (17)	C19—C18—C17	123.75 (17)
C6—C5—C10	121.69 (17)	C19—C18—N6	118.16 (17)
N2—C5—C10	106.58 (15)	C17—C18—N6	118.09 (17)
C5—C6—C7	117.37 (17)	C20—C19—C18	115.76 (16)
C5—C6—H6	121.3	C20—C19—H19	122.1
C7—C6—H6	121.3	C18—C19—H19	122.1
C8—C7—C6	119.97 (17)	C19—C20—N4	131.45 (16)
C8—C7—H7	120.0	C19—C20—C15	121.28 (16)
C6—C7—H7	120.0	N4—C20—C15	107.28 (15)
C10—N1—C1—O1	−177.65 (19)	C20—N4—C11—O4	−179.86 (18)
C10—N1—C1—N2	1.7 (2)	C20—N4—C11—N5	0.1 (2)
C5—N2—C1—O1	177.68 (18)	C15—N5—C11—O4	−179.94 (18)
C2—N2—C1—O1	−1.5 (3)	C12—N5—C11—O4	3.2 (3)
C5—N2—C1—N1	−1.7 (2)	C15—N5—C11—N4	0.1 (2)
C2—N2—C1—N1	179.04 (16)	C12—N5—C11—N4	−176.74 (17)
C5—N2—C2—C3	−64.0 (2)	C11—N5—C12—C13	−120.6 (2)
C1—N2—C2—C3	115.0 (2)	C15—N5—C12—C13	63.0 (3)
C1—N2—C5—C6	−178.67 (19)	C11—N5—C15—C16	179.53 (19)
C2—N2—C5—C6	0.5 (3)	C12—N5—C15—C16	−3.7 (3)
C1—N2—C5—C10	1.1 (2)	C11—N5—C15—C20	−0.27 (19)
C2—N2—C5—C10	−179.73 (17)	C12—N5—C15—C20	176.45 (17)
N2—C5—C6—C7	−179.67 (18)	N5—C15—C16—C17	−179.89 (18)
C10—C5—C6—C7	0.6 (3)	C20—C15—C16—C17	−0.1 (3)
C5—C6—C7—C8	−0.8 (3)	C15—C16—C17—C18	−0.2 (3)
C6—C7—C8—C9	0.4 (3)	C16—C17—C18—C19	0.1 (3)
C6—C7—C8—N3	179.11 (16)	C16—C17—C18—N6	−179.55 (17)
O3—N3—C8—C7	172.97 (18)	O5—N6—C18—C19	175.1 (2)
O2—N3—C8—C7	−8.4 (3)	O6—N6—C18—C19	−4.0 (3)
O3—N3—C8—C9	−8.3 (3)	O5—N6—C18—C17	−5.2 (3)
O2—N3—C8—C9	170.30 (18)	O6—N6—C18—C17	175.7 (2)
C7—C8—C9—C10	0.1 (3)	C17—C18—C19—C20	0.2 (3)
N3—C8—C9—C10	−178.55 (15)	N6—C18—C19—C20	179.91 (16)
C8—C9—C10—N1	179.90 (18)	C18—C19—C20—N4	179.50 (18)
C8—C9—C10—C5	−0.3 (2)	C18—C19—C20—C15	−0.5 (2)
C1—N1—C10—C9	178.72 (19)	C11—N4—C20—C19	179.75 (18)
C1—N1—C10—C5	−1.1 (2)	C11—N4—C20—C15	−0.23 (19)
C6—C5—C10—C9	−0.1 (3)	C16—C15—C20—C19	0.5 (3)
N2—C5—C10—C9	−179.84 (15)	N5—C15—C20—C19	−179.68 (15)
C6—C5—C10—N1	179.78 (16)	C16—C15—C20—N4	−179.52 (16)
N2—C5—C10—N1	0.01 (19)	N5—C15—C20—N4	0.30 (18)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O4	0.96 (2)	1.81 (3)	2.766 (2)	173 (2)
N4—H4···O1	0.92 (2)	1.91 (2)	2.823 (2)	172 (2)
C4—H41···O3i	0.92 (4)	2.39 (4)	3.231 (4)	153 (3)
C14—H141···O6ii	0.88 (3)	2.51 (3)	3.383 (4)	169 (3)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O4	0.96 (2)	1.81 (3)	2.766 (2)	173 (2)
N4—H4⋯O1	0.92 (2)	1.91 (2)	2.823 (2)	172 (2)
C4—H41⋯O3i	0.92 (4)	2.39 (4)	3.231 (4)	153 (3)
C14—H141⋯O6ii	0.88 (3)	2.51 (3)	3.383 (4)	169 (3)

Symmetry codes: (i) ; (ii) .