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ISSN: 2056-9890

N,N-Bis(4-nitro­phen­yl)acetamide

aDepartment of Material Science and Chemistry, Wakayama University, Sakaedani, Wakayama, 640-8510, Japan
*Correspondence e-mail: okuno@center.wakayama-u.ac.jp

(Received 6 February 2013; accepted 22 February 2013; online 28 February 2013)

In the title compound, C14H11N3O5, the dihedral angles between the amide group (r.m.s. deviation = 0.0429 Å) and the two benzene rings are 39.66 (6) and 63.04 (7)°. The dihedral angle between the benzene rings is 86.04 (7)°. The benzene rings form dihedral angles of 4.42 (5) and 8.91 (5)° with the adjacent nitro groups. In the crystal, mol­ecules are linked via a pair of C—H⋯O hydrogen bonds, forming inversion dimers, which are linked via a second pair of C—H⋯O hydrogen bonds, forming chains propagating along [100].

Related literature

For the related structures of diphenyl­acetamide derivatives, see: Kim et al. (2003[Kim, S. Y., An, G. & Rhee, H. (2003). Synlett, pp. 112-114.]); Krigbaum et al. (1968[Krigbaum, W. R., Roe, R.-J. & Woods, J. D. (1968). Acta Cryst. B24, 1304-1312.]); Yamasaki et al. (2003[Yamasaki, R., Tanatani, A., Azumaya, I., Saito, S., Yamaguchi, K. & Kagechika, H. (2003). Org. Lett. 5, 1265-1267.]).

[Scheme 1]

Experimental

Crystal data
  • C14H11N3O5

  • Mr = 301.26

  • Triclinic, [P \overline 1]

  • a = 7.454 (3) Å

  • b = 8.070 (4) Å

  • c = 12.078 (5) Å

  • α = 81.449 (10)°

  • β = 74.676 (10)°

  • γ = 88.062 (13)°

  • V = 692.9 (6) Å3

  • Z = 2

  • Mo Kα radiation

  • μ = 0.11 mm−1

  • T = 93 K

  • 0.10 × 0.10 × 0.08 mm

Data collection
  • Rigaku Saturn724+ diffractometer

  • Absorption correction: numerical (NUMABS; Rigaku, 1999[Rigaku (1999). NUMABS. Rigaku Corporation, Tokyo, Japan.]) Tmin = 0.984, Tmax = 0.991

  • 4684 measured reflections

  • 2397 independent reflections

  • 2038 reflections with F2 > 2σ(F2)

  • Rint = 0.096

Refinement
  • R[F2 > 2σ(F2)] = 0.053

  • wR(F2) = 0.138

  • S = 1.06

  • 2397 reflections

  • 200 parameters

  • H-atom parameters constrained

  • Δρmax = 0.27 e Å−3

  • Δρmin = −0.27 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
C3—H3⋯O5i 0.95 2.39 3.183 (3) 141
C8—H8⋯O5ii 0.95 2.34 3.204 (3) 152
Symmetry codes: (i) -x-1, -y, -z+1; (ii) -x, -y, -z+1.

Data collection: CrystalClear (Rigaku, 2008[Rigaku (2008). CrystalClear. Rigaku Corporation, Tokyo, Japan.]); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXD (Schneider, et al., 2002[Schneider, T. R. & Sheldrick, G. M. (2002). Acta Cryst. D58, 1772-1779.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]); software used to prepare material for publication: CrystalStructure (Rigaku, 2010[Rigaku (2010). CrystalStructure. Rigaku Corporation, Tokyo, Japan.]).

Supporting information


Comment top

The title compound, C14H11N3O5, is a derivative of diphenylacetamides, whose structures are paid attention because of relationship between their structures and molecular recognition functions (Yamasaki et al., 2003).

The structure of the C1/C7/N1/C13/O5/C14 amide group is almost planar (r.m.s. deviation = 0.0429 Å) The dihedral angles of the plane of the amide group with the C1—C6 phenyl ring and the C7—C12 phenyl ring are 39.66 (6)° and 63.04 (7)°, respectively. The dihedral angle between the two phenyl rings is 86.04 (7)°. In diphenylacetamide derivatives, electron deficient aromatic rings have a tendency to make a smaller dihedral angle to an amide part (Kim et al., 2003; Krigbaum et al., 1968; Yamasaki et al., 2003). The obtained geometry has a good agreement with the tendency.

The dihedral angle of the N2/O1/O2 nitro group with the C1—C6 phenyl ring are 8.91 (5)°. The dihedral angle of the N3/O3/O4 nitro group with the C7—C12 phenyl ring is 4.42 (5)°. The nitro groups have good conjugations with the corresponding phenyl groups. Intermolecular contacts are observed beween the nitro groups related by an inversion symmetry, where O4···N2i and N2···O4i are 2.948 (3) Å [Symmetry code: (i) -x, -y, -z].

Related literature top

For the related structures of diphenylacetamide derivatives, see: Kim et al. (2003); Krigbaum et al. (1968); Yamasaki et al. (2003).

Experimental top

Single crystals with sufficient quality for X-ray crystallographical analysis were prepared by recrystallization from a mixed solution of dichloromethane and hexane.

Refinement top

The C-bound H atoms were placed at ideal positions and were refined as riding on their parent C atoms. Uiso(H) values of the H atoms were set at 1.2Ueq(parent atom).

Computing details top

Data collection: CrystalClear (Rigaku, 2008); cell refinement: CrystalClear (Rigaku, 2008); data reduction: CrystalClear (Rigaku, 2008); program(s) used to solve structure: SHELXD (Schneider, et al., 2002); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012); software used to prepare material for publication: CrystalStructure (Rigaku, 2010).

Figures top
[Figure 1] Fig. 1. The asymmetric unit of the title compound with atom-numbering scheme. Displacement ellipsoids are drawn at the 50% probability level and H atoms are shown as small spheres.
[Figure 2] Fig. 2. A view of the intermolecular interactions in the title compound. [Symmetry code: (i) -x, -y, -z.]
N,N-Bis(4-nitrophenyl)acetamide top
Crystal data top
C14H11N3O5Z = 2
Mr = 301.26F(000) = 312.00
Triclinic, P1Dx = 1.444 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71075 Å
a = 7.454 (3) ÅCell parameters from 1648 reflections
b = 8.070 (4) Åθ = 1.8–25.0°
c = 12.078 (5) ŵ = 0.11 mm1
α = 81.449 (10)°T = 93 K
β = 74.676 (10)°Platelet, colourless
γ = 88.062 (13)°0.10 × 0.10 × 0.08 mm
V = 692.9 (6) Å3
Data collection top
Rigaku Saturn724+
diffractometer
2038 reflections with F2 > 2σ(F2)
Detector resolution: 28.445 pixels mm-1Rint = 0.096
ω scansθmax = 25.0°
Absorption correction: numerical
(NUMABS; Rigaku, 1999)
h = 88
Tmin = 0.984, Tmax = 0.991k = 99
4684 measured reflectionsl = 1414
2397 independent reflections
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.053Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.138H-atom parameters constrained
S = 1.06 w = 1/[σ2(Fo2) + (0.0625P)2 + 0.2501P]
where P = (Fo2 + 2Fc2)/3
2397 reflections(Δ/σ)max < 0.001
200 parametersΔρmax = 0.27 e Å3
0 restraintsΔρmin = 0.27 e Å3
Primary atom site location: structure-invariant direct methods
Crystal data top
C14H11N3O5γ = 88.062 (13)°
Mr = 301.26V = 692.9 (6) Å3
Triclinic, P1Z = 2
a = 7.454 (3) ÅMo Kα radiation
b = 8.070 (4) ŵ = 0.11 mm1
c = 12.078 (5) ÅT = 93 K
α = 81.449 (10)°0.10 × 0.10 × 0.08 mm
β = 74.676 (10)°
Data collection top
Rigaku Saturn724+
diffractometer
2397 independent reflections
Absorption correction: numerical
(NUMABS; Rigaku, 1999)
2038 reflections with F2 > 2σ(F2)
Tmin = 0.984, Tmax = 0.991Rint = 0.096
4684 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0530 restraints
wR(F2) = 0.138H-atom parameters constrained
S = 1.06Δρmax = 0.27 e Å3
2397 reflectionsΔρmin = 0.27 e Å3
200 parameters
Special details top

Refinement. Refinement was performed using all reflections. The weighted R-factor (wR) and goodness of fit (S) are based on F2. R-factor (gt) are based on F. The threshold expression of F2 > 2.0 σ(F2) is used only for calculating R-factor (gt).

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
O10.5557 (2)0.5404 (2)0.37979 (13)0.0390 (4)
O20.3035 (2)0.6254 (2)0.26745 (17)0.0472 (5)
O30.74805 (19)0.2913 (3)0.02433 (13)0.0439 (5)
O40.5763 (3)0.3680 (3)0.13945 (14)0.0527 (6)
O50.19693 (17)0.09710 (17)0.50403 (11)0.0252 (4)
N10.03594 (19)0.0866 (2)0.31681 (13)0.0197 (4)
N20.3953 (3)0.5182 (3)0.31981 (16)0.0303 (5)
N30.5958 (3)0.3042 (3)0.04519 (14)0.0297 (5)
C10.1318 (3)0.0612 (3)0.31114 (15)0.0202 (4)
C20.3232 (3)0.0792 (3)0.35967 (16)0.0220 (5)
C30.4102 (3)0.2286 (3)0.36144 (16)0.0234 (5)
C40.3058 (3)0.3557 (3)0.31174 (16)0.0235 (5)
C50.1181 (3)0.3371 (3)0.25680 (17)0.0252 (5)
C60.0311 (3)0.1892 (3)0.25763 (17)0.0247 (5)
C70.1247 (3)0.1395 (3)0.22310 (16)0.0214 (5)
C80.3012 (3)0.1129 (3)0.24046 (17)0.0300 (5)
C90.4555 (3)0.1664 (3)0.15180 (17)0.0307 (5)
C100.4306 (3)0.2425 (3)0.04780 (16)0.0238 (5)
C110.2570 (3)0.2667 (3)0.02760 (17)0.0330 (5)
C120.1024 (3)0.2137 (3)0.11739 (17)0.0299 (5)
C130.0767 (3)0.1569 (3)0.41913 (16)0.0213 (5)
C140.0321 (3)0.3092 (3)0.42132 (18)0.0290 (5)
H20.39360.01100.39140.0264*
H30.53980.24330.39630.0280*
H50.05060.42420.21930.0302*
H60.09820.17470.22150.0297*
H80.31540.05820.31290.0360*
H90.57690.15080.16270.0368*
H110.24380.31830.04580.0396*
H120.01880.22850.10600.0358*
H14A0.07860.36790.34220.0347*
H14B0.13730.27490.45380.0347*
H14C0.04860.38410.46950.0347*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0354 (9)0.0405 (10)0.0406 (9)0.0158 (7)0.0123 (7)0.0037 (8)
O20.0371 (9)0.0279 (9)0.0846 (14)0.0051 (7)0.0246 (9)0.0190 (9)
O30.0219 (8)0.0775 (14)0.0301 (9)0.0079 (8)0.0056 (7)0.0009 (9)
O40.0369 (9)0.0839 (15)0.0282 (9)0.0039 (9)0.0072 (7)0.0190 (9)
O50.0200 (7)0.0326 (8)0.0224 (7)0.0023 (6)0.0038 (6)0.0061 (6)
N10.0151 (8)0.0236 (9)0.0205 (8)0.0001 (6)0.0051 (6)0.0026 (7)
N20.0272 (10)0.0289 (10)0.0390 (10)0.0025 (8)0.0184 (8)0.0001 (8)
N30.0267 (9)0.0390 (11)0.0221 (9)0.0034 (8)0.0047 (7)0.0027 (8)
C10.0174 (9)0.0244 (10)0.0198 (9)0.0003 (8)0.0080 (7)0.0006 (8)
C20.0171 (9)0.0281 (11)0.0215 (9)0.0042 (8)0.0066 (8)0.0037 (8)
C30.0158 (9)0.0306 (11)0.0237 (10)0.0009 (8)0.0067 (8)0.0008 (9)
C40.0221 (10)0.0233 (11)0.0266 (10)0.0025 (8)0.0118 (8)0.0017 (8)
C50.0213 (10)0.0262 (11)0.0299 (11)0.0040 (8)0.0087 (8)0.0073 (9)
C60.0154 (9)0.0303 (11)0.0283 (10)0.0016 (8)0.0051 (8)0.0052 (9)
C70.0186 (9)0.0236 (10)0.0227 (10)0.0017 (8)0.0056 (8)0.0050 (8)
C80.0226 (10)0.0429 (13)0.0232 (10)0.0003 (9)0.0080 (8)0.0034 (9)
C90.0179 (10)0.0480 (14)0.0268 (11)0.0016 (9)0.0083 (8)0.0025 (10)
C100.0198 (10)0.0280 (11)0.0228 (10)0.0026 (8)0.0034 (8)0.0048 (9)
C110.0289 (11)0.0468 (14)0.0220 (10)0.0019 (10)0.0092 (9)0.0032 (10)
C120.0192 (10)0.0457 (13)0.0257 (10)0.0003 (9)0.0093 (8)0.0021 (10)
C130.0167 (9)0.0247 (11)0.0243 (10)0.0062 (8)0.0089 (8)0.0039 (8)
C140.0300 (11)0.0314 (12)0.0279 (11)0.0031 (9)0.0104 (9)0.0062 (9)
Geometric parameters (Å, º) top
O1—N21.226 (3)C7—C121.376 (3)
O2—N21.229 (3)C8—C91.379 (3)
O3—N31.224 (3)C9—C101.369 (3)
O4—N31.221 (3)C10—C111.382 (3)
O5—C131.218 (2)C11—C121.386 (3)
N1—C11.430 (3)C13—C141.502 (3)
N1—C71.439 (2)C2—H20.950
N1—C131.393 (3)C3—H30.950
N2—C41.470 (3)C5—H50.950
N3—C101.473 (3)C6—H60.950
C1—C21.395 (3)C8—H80.950
C1—C61.392 (3)C9—H90.950
C2—C31.383 (3)C11—H110.950
C3—C41.379 (3)C12—H120.950
C4—C51.384 (3)C14—H14A0.980
C5—C61.380 (3)C14—H14B0.980
C7—C81.391 (3)C14—H14C0.980
O1···C32.730 (3)H11···H122.3500
O1···C53.552 (3)H12···H14A3.4692
O2···C33.551 (3)O1···H3i3.2240
O2···C52.716 (3)O1···H14Aiii3.0122
O3···C92.712 (3)O1···H14Biii2.6480
O3···C113.554 (3)O1···H14Ciii3.5911
O4···C93.543 (3)O1···H14Cix3.3464
O4···C112.740 (3)O2···H2iv3.0985
O5···C12.746 (3)O2···H9iii2.6542
O5···C22.765 (3)O2···H11ii3.3131
O5···C73.576 (3)O2···H12iv2.8331
C1···C42.744 (3)O2···H14Aiv3.2039
C1···C83.408 (3)O2···H14Civ3.4762
C1···C123.163 (3)O3···H5v2.8961
C2···C52.786 (3)O3···H6v2.6499
C2···C132.977 (3)O3···H11vi3.3887
C3···C62.780 (3)O3···H12vii2.6276
C6···C72.860 (3)O4···H3ii3.4790
C6···C83.480 (4)O4···H5v3.4369
C6···C123.481 (4)O4···H6v2.8701
C6···C133.595 (4)O4···H14Avi3.5560
C7···C102.725 (3)O5···H2ix3.0802
C7···C142.850 (4)O5···H3ix2.3895
C8···C112.780 (3)O5···H8viii2.3362
C8···C133.109 (3)O5···H14Bviii3.0071
C8···C143.131 (3)N2···H3i3.5938
C9···C122.776 (3)N2···H9iii3.5400
C12···C133.500 (3)N2···H11ii3.3749
O1···O1i3.380 (3)N2···H14Civ3.5320
O1···O4ii3.067 (3)N3···H5v3.5638
O1···C3i3.345 (3)N3···H6v2.9605
O1···C4i3.570 (3)C1···H9xii3.4281
O1···C14iii3.228 (3)C1···H14Bviii3.0862
O2···O4ii3.355 (3)C2···H2ix3.2949
O2···N1iv3.105 (3)C2···H8xii3.0367
O2···C9iii3.199 (4)C2···H9xii3.0316
O2···C12iv3.415 (3)C2···H14Bviii3.1521
O2···C13iv3.128 (3)C3···H8xii3.1294
O2···C14iv3.474 (4)C3···H14Bviii3.3704
O3···C5v3.361 (3)C4···H11ii3.0913
O3···C6v3.240 (3)C4···H14Bviii3.5370
O3···C11vi3.560 (4)C4···H14Civ3.4905
O3···C12vii3.501 (3)C5···H11ii2.9211
O4···O1ii3.067 (3)C5···H14Aiv2.9518
O4···O2ii3.355 (3)C5···H14Bviii3.5699
O4···N2ii2.948 (3)C5···H14Civ3.2916
O4···C3ii3.568 (4)C6···H14Bviii3.3341
O4···C4ii3.270 (3)C8···H2vii3.2859
O4···C10vi3.479 (4)C8···H3vii3.5429
O5···O5viii3.266 (3)C9···H2vii3.4298
O5···N1viii3.279 (3)C12···H5x3.3853
O5···C2ix3.518 (3)C13···H3ix3.2539
O5···C3ix3.183 (3)C13···H8viii3.4855
O5···C8viii3.204 (3)C13···H14Bviii3.5847
O5···C13viii3.062 (3)C14···H5x3.1790
O5···C14viii3.536 (3)C14···H14Cxiii2.9936
N1···O2x3.105 (3)H2···O2x3.0985
N1···O5viii3.279 (3)H2···O5ix3.0802
N2···O4ii2.948 (3)H2···C2ix3.2949
C2···O5ix3.518 (3)H2···C8xii3.2859
C3···O1i3.345 (3)H2···C9xii3.4298
C3···O4ii3.568 (4)H2···H2ix2.6662
C3···O5ix3.183 (3)H2···H3ix3.3208
C4···O1i3.570 (3)H2···H8xii2.5836
C4···O4ii3.270 (3)H2···H9xii2.8867
C5···O3v3.361 (3)H2···H14Bviii3.5740
C5···C14iv3.553 (3)H3···O1i3.2240
C6···O3v3.240 (3)H3···O4ii3.4790
C8···O5viii3.204 (3)H3···O5ix2.3895
C9···O2xi3.199 (4)H3···N2i3.5938
C10···O4vi3.479 (4)H3···C8xii3.5429
C11···O3vi3.560 (4)H3···C13ix3.2539
C12···O2x3.415 (3)H3···H2ix3.3208
C12···O3xii3.501 (3)H3···H8xii2.7875
C13···O2x3.128 (3)H3···H14Cix3.2232
C13···O5viii3.062 (3)H5···O3v2.8961
C13···C13viii3.324 (3)H5···O4v3.4369
C14···O1xi3.228 (3)H5···N3v3.5638
C14···O2x3.474 (4)H5···C12iv3.3853
C14···O5viii3.536 (3)H5···C14iv3.1790
C14···C5x3.553 (3)H5···H11ii2.8595
O1···H32.4445H5···H12iv3.2729
O2···H52.4240H5···H14Aiv2.4184
O3···H92.4141H5···H14Civ3.1864
O4···H112.4557H6···O3v2.6499
O5···H22.4258H6···O4v2.8701
O5···H14A3.1191H6···N3v2.9605
O5···H14B2.7956H8···O5viii2.3362
O5···H14C2.5300H8···C2vii3.0367
N1···H22.6396H8···C3vii3.1294
N1···H62.5961H8···C13viii3.4855
N1···H82.6096H8···H2vii2.5836
N1···H122.6044H8···H3vii2.7875
N1···H14A2.5407H9···O2xi2.6542
N1···H14B2.9533H9···N2xi3.5400
N1···H14C3.2219H9···C1vii3.4281
N2···H32.6186H9···C2vii3.0316
N2···H52.6197H9···H2vii2.8867
N3···H92.5992H9···H12vii2.9759
N3···H112.6241H11···O2ii3.3131
C1···H33.2660H11···O3vi3.3887
C1···H53.2663H11···N2ii3.3749
C1···H83.5073H11···C4ii3.0913
C1···H123.1019H11···C5ii2.9211
C2···H63.2698H11···H5ii2.8595
C3···H53.2729H12···O2x2.8331
C4···H23.2393H12···O3xii2.6276
C4···H63.2372H12···H5x3.2729
C5···H33.2729H12···H9xii2.9759
C6···H23.2704H14A···O1xi3.0122
C6···H83.5719H14A···O2x3.2039
C6···H123.5807H14A···O4vi3.5560
C7···H62.5530H14A···C5x2.9518
C7···H93.2561H14A···H5x2.4184
C7···H113.2541H14A···H14Cxiii3.2074
C7···H14A2.4635H14B···O1xi2.6480
C7···H14B3.1646H14B···O5viii3.0071
C8···H62.8821H14B···C1viii3.0862
C8···H123.2625H14B···C2viii3.1521
C8···H14A2.8181H14B···C3viii3.3704
C8···H14B3.0116H14B···C4viii3.5370
C9···H113.2675H14B···C5viii3.5699
C10···H83.2278H14B···C6viii3.3341
C10···H123.2382H14B···C13viii3.5847
C11···H93.2672H14B···H2viii3.5740
C12···H63.1965H14B···H14Cxiii3.0306
C12···H83.2615H14C···O1xi3.5911
C12···H14A3.1125H14C···O1ix3.3464
C13···H22.7932H14C···O2x3.4762
C13···H82.9975H14C···N2x3.5320
C14···H83.0518H14C···C4x3.4905
H2···H32.3419H14C···C5x3.2916
H5···H62.3380H14C···C14xiii2.9936
H6···H83.0232H14C···H3ix3.2232
H6···H123.5205H14C···H5x3.1864
H8···H92.3401H14C···H14Axiii3.2074
H8···H14A3.0202H14C···H14Bxiii3.0306
H8···H14B2.6923H14C···H14Cxiii2.3144
C1—N1—C7117.73 (16)C10—C11—C12118.19 (19)
C1—N1—C13120.10 (14)C7—C12—C11119.90 (19)
C7—N1—C13121.12 (17)O5—C13—N1121.08 (18)
O1—N2—O2123.71 (19)O5—C13—C14121.06 (19)
O1—N2—C4118.39 (17)N1—C13—C14117.86 (15)
O2—N2—C4117.88 (16)C1—C2—H2120.083
O3—N3—O4122.36 (16)C3—C2—H2120.077
O3—N3—C10118.43 (17)C2—C3—H3120.539
O4—N3—C10119.20 (17)C4—C3—H3120.544
N1—C1—C2120.95 (17)C4—C5—H5120.727
N1—C1—C6119.08 (15)C6—C5—H5120.731
C2—C1—C6119.96 (19)C1—C6—H6119.844
C1—C2—C3119.84 (18)C5—C6—H6119.836
C2—C3—C4118.92 (16)C7—C8—H8120.234
N2—C4—C3119.07 (16)C9—C8—H8120.228
N2—C4—C5118.67 (17)C8—C9—H9120.571
C3—C4—C5122.24 (19)C10—C9—H9120.567
C4—C5—C6118.54 (18)C10—C11—H11120.906
C1—C6—C5120.32 (16)C12—C11—H11120.905
N1—C7—C8119.28 (17)C7—C12—H12120.047
N1—C7—C12119.89 (17)C11—C12—H12120.052
C8—C7—C12120.83 (16)C13—C14—H14A109.475
C7—C8—C9119.54 (19)C13—C14—H14B109.471
C8—C9—C10118.86 (19)C13—C14—H14C109.473
N3—C10—C9118.49 (17)H14A—C14—H14B109.467
N3—C10—C11118.85 (17)H14A—C14—H14C109.475
C9—C10—C11122.65 (16)H14B—C14—H14C109.467
C1—N1—C7—C8104.8 (2)N1—C1—C2—C3174.74 (15)
C1—N1—C7—C1274.4 (3)N1—C1—C6—C5176.24 (15)
C7—N1—C1—C2148.93 (15)C2—C1—C6—C52.9 (3)
C7—N1—C1—C632.0 (3)C6—C1—C2—C34.4 (3)
C1—N1—C13—O51.9 (3)C1—C2—C3—C41.9 (3)
C1—N1—C13—C14178.27 (14)C2—C3—C4—N2176.24 (16)
C13—N1—C1—C242.7 (3)C2—C3—C4—C52.1 (3)
C13—N1—C1—C6136.44 (16)N2—C4—C5—C6174.77 (16)
C7—N1—C13—O5169.91 (16)C3—C4—C5—C63.6 (3)
C7—N1—C13—C1410.3 (3)C4—C5—C6—C11.0 (3)
C13—N1—C7—C863.5 (3)N1—C7—C8—C9178.66 (17)
C13—N1—C7—C12117.3 (2)N1—C7—C12—C11179.13 (17)
O1—N2—C4—C36.7 (3)C8—C7—C12—C111.7 (4)
O1—N2—C4—C5171.77 (17)C12—C7—C8—C92.1 (4)
O2—N2—C4—C3174.59 (18)C7—C8—C9—C101.0 (4)
O2—N2—C4—C57.0 (3)C8—C9—C10—N3178.05 (19)
O3—N3—C10—C93.0 (3)C8—C9—C10—C110.5 (4)
O3—N3—C10—C11175.68 (18)N3—C10—C11—C12177.59 (18)
O4—N3—C10—C9177.92 (19)C9—C10—C11—C121.0 (4)
O4—N3—C10—C113.4 (3)C10—C11—C12—C70.1 (4)
Symmetry codes: (i) x1, y1, z+1; (ii) x, y, z; (iii) x1, y1, z; (iv) x, y1, z; (v) x+1, y, z; (vi) x+1, y+1, z; (vii) x+1, y, z; (viii) x, y, z+1; (ix) x1, y, z+1; (x) x, y+1, z; (xi) x+1, y+1, z; (xii) x1, y, z; (xiii) x, y+1, z+1.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C3—H3···O5ix0.952.393.183 (3)141
C8—H8···O5viii0.952.343.204 (3)152
Symmetry codes: (viii) x, y, z+1; (ix) x1, y, z+1.

Experimental details

Crystal data
Chemical formulaC14H11N3O5
Mr301.26
Crystal system, space groupTriclinic, P1
Temperature (K)93
a, b, c (Å)7.454 (3), 8.070 (4), 12.078 (5)
α, β, γ (°)81.449 (10), 74.676 (10), 88.062 (13)
V3)692.9 (6)
Z2
Radiation typeMo Kα
µ (mm1)0.11
Crystal size (mm)0.10 × 0.10 × 0.08
Data collection
DiffractometerRigaku Saturn724+
diffractometer
Absorption correctionNumerical
(NUMABS; Rigaku, 1999)
Tmin, Tmax0.984, 0.991
No. of measured, independent and
observed [F2 > 2σ(F2)] reflections
4684, 2397, 2038
Rint0.096
(sin θ/λ)max1)0.595
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.053, 0.138, 1.06
No. of reflections2397
No. of parameters200
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.27, 0.27

Computer programs: CrystalClear (Rigaku, 2008), SHELXD (Schneider, et al., 2002), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 2012), CrystalStructure (Rigaku, 2010).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C3—H3···O5i0.952.393.183 (3)141
C8—H8···O5ii0.952.343.204 (3)152
Symmetry codes: (i) x1, y, z+1; (ii) x, y, z+1.
 

Acknowledgements

This work was supported by Research for Promoting Technological Seeds from the Japan Science and Technology Agency (JST).

References

First citationFarrugia, L. J. (2012). J. Appl. Cryst. 45, 849–854.  Web of Science CrossRef CAS IUCr Journals
First citationKim, S. Y., An, G. & Rhee, H. (2003). Synlett, pp. 112–114.
First citationKrigbaum, W. R., Roe, R.-J. & Woods, J. D. (1968). Acta Cryst. B24, 1304–1312.  CSD CrossRef CAS IUCr Journals Web of Science
First citationRigaku (1999). NUMABS. Rigaku Corporation, Tokyo, Japan.
First citationRigaku (2008). CrystalClear. Rigaku Corporation, Tokyo, Japan.
First citationRigaku (2010). CrystalStructure. Rigaku Corporation, Tokyo, Japan.
First citationSchneider, T. R. & Sheldrick, G. M. (2002). Acta Cryst. D58, 1772–1779.  Web of Science CrossRef CAS IUCr Journals
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals
First citationYamasaki, R., Tanatani, A., Azumaya, I., Saito, S., Yamaguchi, K. & Kagechika, H. (2003). Org. Lett. 5, 1265–1267.  Web of Science CSD CrossRef PubMed CAS

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