organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

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ISSN: 2056-9890

4-(Di­methyl­amino)­benzaldehyde–2,4-di­nitro­aniline (1/1)

aDepartment of Chemistry, Taiyuan Normal University, Taiyuan 030031, People's Republic of China
*Correspondence e-mail: ruitaozhu@126.com

(Received 6 June 2011; accepted 9 June 2011; online 18 June 2011)

The asymmetric unit of the title compound, C9H11NO·C6H5N3O4, contains two independent mol­ecules each of 4-(dimethyl­amino)­benzaldehyde and 2,4-dinitro­aniline. In the crystal, the components are linked by inter­molecular N—H⋯O hydrogen bonds to form one-dimensional chains along [10[\overline{1}]]. Intra­molecular N—H⋯O hydrogen bonds are also present.

Related literature

For related structures, see: Nesterov et al. (2000[Nesterov, V. N., Timofeeva, T. V., Antipin, M. Y. & Clark, R. D. (2000). Acta Cryst. C56, 976-978.]); Weber & Sheldrick (1981[Weber, G. & Sheldrick, G. M. (1981). Acta Cryst. B37, 2108-2111.]). For standard bond-length data, see: Allen et al. (1987[Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1-19.]).

[Scheme 1]

Experimental

Crystal data
  • C9H11NO·C6H5N3O4

  • Mr = 332.32

  • Monoclinic, P 21 /n

  • a = 18.7512 (18) Å

  • b = 7.3182 (6) Å

  • c = 24.338 (2) Å

  • β = 109.493 (1)°

  • V = 3148.4 (5) Å3

  • Z = 8

  • Mo Kα radiation

  • μ = 0.11 mm−1

  • T = 298 K

  • 0.48 × 0.18 × 0.11 mm

Data collection
  • Bruker SMART CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2007[Bruker (2007). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.950, Tmax = 0.988

  • 15396 measured reflections

  • 5547 independent reflections

  • 2303 reflections with I > 2σ(I)

  • Rint = 0.060

Refinement
  • R[F2 > 2σ(F2)] = 0.048

  • wR(F2) = 0.087

  • S = 1.02

  • 5547 reflections

  • 433 parameters

  • 6 restraints

  • H-atom parameters constrained

  • Δρmax = 0.17 e Å−3

  • Δρmin = −0.20 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
N1—H1A⋯O10i 0.86 2.18 3.010 (3) 163
N1—H1B⋯O1 0.86 2.03 2.640 (3) 127
N1—H1B⋯O7ii 0.86 2.49 3.170 (3) 136
N4—H4A⋯O9iii 0.86 2.04 2.889 (3) 171
N4—H4B⋯O5 0.86 2.02 2.636 (3) 128
N4—H4B⋯O3iii 0.86 2.42 3.047 (3) 130
Symmetry codes: (i) [x-{\script{1\over 2}}, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]; (ii) [-x+{\script{1\over 2}}, y-{\script{1\over 2}}, -z+{\script{3\over 2}}]; (iii) -x+1, -y+1, -z+1.

Data collection: SMART (Bruker, 2007[Bruker (2007). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2007[Bruker (2007). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]) and PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]); software used to prepare material for publication: SHELXTL.

Supporting information


Comment top

The crystal structures of some molecular complexes of 2,4-dinitroaniline have already been published (Nesterov et al., 2000; Weber & Sheldrick, 1981). In this paper, we present the crystal structure of the title compound (I).

The molecular structure of (I) is shown in Fig. 1. The bond lengths (Allen et al., 1987) and angles are normal . The asymmetric unit contains two independent molecules of 4-(dimethylamino)benzaldehyde and two indpendent molecules of 2,4-Dinitroaniline. In the crystal, the components are linked by intermolecular N—H···O hydrogen bonds to form one-dimensional chains along [101].

Related literature top

For related structures, see: Nesterov et al. (2000); Weber & Sheldrick (1981). For standard bond-length data, see: Allen et al. (1987).

Experimental top

A mixture of 4-(dimethylamino)benzaldehyde (0.75 g, 5 mmol) and 2,4-dinitroaniline (0.92 g, 5 mmol) were refluxed in ethanol (50 ml) for 30 min and rotary evaporated. Recrystallization from ethanol solution produced the crystals of the title compound.

Refinement top

H atoms were placed in idealized positions and allowed to ride on their respective parent atoms, with C—H = 0.93–0.96 Å, N—H = 0.86Å and Uiso(H)= 1.2Ueq(C,N) or 1.5Ueq(Cmethyl).

Computing details top

Data collection: SMART (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. The molecular structure of the title compound with displacement ellipsoids are drawn at the 30% probability level.
[Figure 2] Fig. 2. Part of the crystal structure of (I) with hydrogen bonds drawn as dashed lines. Only H atoms involved in hydrogen bonds are shown.
4-(Dimethylamino)benzaldehyde–2,4-dinitroaniline (1/1) top
Crystal data top
C9H11NO·C6H5N3O4F(000) = 1392
Mr = 332.32Dx = 1.402 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 1665 reflections
a = 18.7512 (18) Åθ = 2.5–20.6°
b = 7.3182 (6) ŵ = 0.11 mm1
c = 24.338 (2) ÅT = 298 K
β = 109.493 (1)°Flake, colorless
V = 3148.4 (5) Å30.48 × 0.18 × 0.11 mm
Z = 8
Data collection top
Bruker SMART CCD
diffractometer
5547 independent reflections
Radiation source: fine-focus sealed tube2303 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.060
ϕ and ω scansθmax = 25.0°, θmin = 2.4°
Absorption correction: multi-scan
(SADABS; Bruker, 2007)
h = 2216
Tmin = 0.950, Tmax = 0.988k = 88
15396 measured reflectionsl = 2728
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.048Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.087H-atom parameters constrained
S = 1.02 w = 1/[σ2(Fo2) + (0.0105P)2]
where P = (Fo2 + 2Fc2)/3
5547 reflections(Δ/σ)max < 0.001
433 parametersΔρmax = 0.17 e Å3
6 restraintsΔρmin = 0.20 e Å3
Crystal data top
C9H11NO·C6H5N3O4V = 3148.4 (5) Å3
Mr = 332.32Z = 8
Monoclinic, P21/nMo Kα radiation
a = 18.7512 (18) ŵ = 0.11 mm1
b = 7.3182 (6) ÅT = 298 K
c = 24.338 (2) Å0.48 × 0.18 × 0.11 mm
β = 109.493 (1)°
Data collection top
Bruker SMART CCD
diffractometer
5547 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2007)
2303 reflections with I > 2σ(I)
Tmin = 0.950, Tmax = 0.988Rint = 0.060
15396 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0486 restraints
wR(F2) = 0.087H-atom parameters constrained
S = 1.02Δρmax = 0.17 e Å3
5547 reflectionsΔρmin = 0.20 e Å3
433 parameters
Special details top

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 (Å2) top
xyzUiso*/Ueq
N10.13405 (12)0.4177 (3)0.64855 (9)0.0680 (7)
H1A0.15700.44590.68440.082*
H1B0.08920.37230.63820.082*
N20.06120 (14)0.3253 (3)0.52459 (12)0.0627 (7)
N30.28629 (16)0.5458 (4)0.49136 (12)0.0659 (8)
N40.62137 (12)0.6263 (3)0.60594 (9)0.0730 (8)
H4A0.59910.65200.56980.088*
H4B0.66610.58020.61720.088*
N50.69136 (14)0.5410 (3)0.73034 (12)0.0640 (7)
N60.46369 (16)0.7627 (3)0.75848 (12)0.0644 (7)
N70.54203 (14)0.1901 (3)0.78750 (11)0.0702 (8)
N80.79608 (13)0.0474 (3)0.53617 (10)0.0672 (7)
O10.02442 (11)0.2921 (3)0.55713 (9)0.0863 (7)
O20.03664 (10)0.2926 (3)0.47188 (9)0.0859 (7)
O30.25494 (12)0.5097 (3)0.43926 (10)0.0856 (7)
O40.34929 (12)0.6141 (3)0.51053 (9)0.0911 (8)
O50.72847 (10)0.4992 (3)0.69840 (9)0.0838 (7)
O60.71548 (10)0.5136 (3)0.78306 (9)0.0864 (7)
O70.49526 (11)0.7428 (3)0.81136 (9)0.0842 (7)
O80.39780 (12)0.8089 (3)0.73743 (9)0.1019 (9)
O90.45542 (14)0.2464 (4)0.51132 (9)0.1171 (10)
O100.72731 (12)0.0839 (3)0.26313 (9)0.0903 (8)
C10.16792 (16)0.4443 (4)0.60916 (12)0.0481 (8)
C20.13580 (14)0.4027 (3)0.54922 (12)0.0450 (7)
C30.17543 (15)0.4359 (3)0.51131 (11)0.0490 (8)
H30.15370.40800.47190.059*
C40.24568 (16)0.5087 (4)0.53145 (13)0.0477 (7)
C50.27963 (15)0.5507 (3)0.59022 (13)0.0516 (8)
H50.32810.60020.60370.062*
C60.24120 (15)0.5186 (4)0.62736 (12)0.0520 (8)
H60.26420.54690.66660.062*
C70.58660 (16)0.6579 (4)0.64448 (12)0.0491 (7)
C80.61777 (14)0.6216 (4)0.70481 (11)0.0472 (7)
C90.57746 (15)0.6585 (4)0.74155 (11)0.0511 (8)
H90.59870.63450.78120.061*
C100.50712 (16)0.7295 (4)0.72008 (12)0.0463 (7)
C110.47405 (15)0.7694 (3)0.66082 (12)0.0507 (8)
H110.42580.81970.64650.061*
C120.51349 (16)0.7334 (4)0.62468 (12)0.0535 (8)
H120.49150.75960.58520.064*
C130.5127 (2)0.2137 (4)0.55089 (14)0.0854 (11)
H130.55530.18560.54100.102*
C140.52185 (17)0.2138 (4)0.61208 (12)0.0536 (8)
C150.46240 (16)0.2653 (4)0.63065 (13)0.0571 (8)
H150.41710.30360.60340.069*
C160.46925 (15)0.2606 (3)0.68821 (13)0.0536 (8)
H160.42880.29800.69950.064*
C170.53573 (17)0.2010 (4)0.73066 (13)0.0516 (8)
C180.59579 (15)0.1494 (4)0.71130 (12)0.0563 (8)
H180.64110.10960.73820.068*
C190.58822 (15)0.1569 (4)0.65354 (13)0.0590 (8)
H190.62880.12290.64190.071*
C200.48038 (17)0.2435 (4)0.80759 (12)0.0838 (11)
H20A0.47400.37360.80450.126*
H20B0.49180.20710.84750.126*
H20C0.43460.18490.78400.126*
C210.61157 (16)0.1308 (4)0.83177 (11)0.0912 (11)
H21A0.62020.00400.82600.137*
H21B0.60730.14720.86970.137*
H21C0.65320.20190.82880.137*
C220.77930 (18)0.0195 (4)0.30214 (14)0.0732 (10)
H220.82080.01960.29250.088*
C230.78384 (17)0.0032 (4)0.36245 (13)0.0523 (8)
C240.72267 (15)0.0435 (3)0.37970 (13)0.0542 (8)
H240.67860.08730.35210.065*
C250.72604 (15)0.0264 (4)0.43635 (13)0.0534 (8)
H250.68380.05520.44660.064*
C260.79240 (16)0.0341 (4)0.47947 (12)0.0495 (8)
C270.85369 (15)0.0821 (4)0.46156 (12)0.0547 (8)
H270.89810.12530.48880.066*
C280.84891 (15)0.0661 (4)0.40456 (13)0.0574 (8)
H280.89040.09820.39380.069*
C290.73431 (16)0.0077 (4)0.55566 (12)0.0807 (10)
H29A0.68930.05740.53390.121*
H29B0.74680.01960.59640.121*
H29C0.72590.13660.54960.121*
C300.86512 (15)0.1111 (4)0.58117 (11)0.0862 (11)
H30A0.90540.02620.58460.129*
H30B0.85640.11950.61780.129*
H30C0.87870.22910.57060.129*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N10.0661 (17)0.091 (2)0.0563 (16)0.0038 (14)0.0327 (14)0.0031 (14)
N20.0510 (15)0.0666 (19)0.0671 (16)0.0032 (14)0.0151 (15)0.0009 (15)
N30.066 (2)0.070 (2)0.073 (2)0.0053 (16)0.0392 (16)0.0088 (16)
N40.0634 (17)0.106 (2)0.0558 (17)0.0032 (15)0.0291 (14)0.0089 (15)
N50.0491 (16)0.074 (2)0.066 (2)0.0013 (13)0.0150 (15)0.0039 (16)
N60.066 (2)0.069 (2)0.064 (2)0.0077 (16)0.0308 (18)0.0010 (15)
N70.0644 (19)0.092 (2)0.0545 (18)0.0014 (15)0.0208 (15)0.0027 (16)
N80.0635 (18)0.088 (2)0.0477 (17)0.0110 (15)0.0159 (15)0.0084 (15)
O10.0620 (15)0.111 (2)0.0961 (18)0.0151 (13)0.0400 (13)0.0025 (14)
O20.0702 (14)0.113 (2)0.0612 (13)0.0207 (12)0.0047 (11)0.0049 (13)
O30.0930 (17)0.113 (2)0.0658 (16)0.0017 (14)0.0470 (14)0.0052 (14)
O40.0623 (15)0.118 (2)0.1038 (18)0.0139 (14)0.0420 (14)0.0113 (15)
O50.0511 (14)0.126 (2)0.0819 (17)0.0089 (13)0.0323 (12)0.0041 (14)
O60.0655 (15)0.129 (2)0.0580 (15)0.0167 (13)0.0118 (12)0.0150 (14)
O70.0899 (17)0.113 (2)0.0571 (15)0.0218 (13)0.0342 (13)0.0084 (13)
O80.0687 (16)0.157 (2)0.0879 (18)0.0381 (16)0.0369 (14)0.0113 (15)
O90.128 (2)0.162 (3)0.0519 (15)0.0101 (18)0.0164 (14)0.0233 (16)
O100.1016 (18)0.112 (2)0.0499 (14)0.0068 (15)0.0155 (12)0.0085 (13)
C10.051 (2)0.046 (2)0.053 (2)0.0062 (15)0.0244 (16)0.0027 (15)
C20.0408 (15)0.045 (2)0.0504 (18)0.0028 (13)0.0170 (12)0.0015 (14)
C30.057 (2)0.048 (2)0.0405 (18)0.0030 (16)0.0148 (16)0.0024 (14)
C40.051 (2)0.047 (2)0.049 (2)0.0000 (16)0.0227 (14)0.0008 (15)
C50.0431 (18)0.049 (2)0.062 (2)0.0000 (15)0.0164 (17)0.0012 (16)
C60.054 (2)0.055 (2)0.0433 (19)0.0025 (16)0.0102 (16)0.0031 (15)
C70.0493 (19)0.050 (2)0.053 (2)0.0094 (16)0.0245 (16)0.0015 (16)
C80.0407 (16)0.057 (2)0.0443 (18)0.0019 (14)0.0142 (15)0.0034 (15)
C90.0520 (19)0.058 (2)0.0426 (18)0.0055 (16)0.0141 (16)0.0020 (15)
C100.051 (2)0.047 (2)0.048 (2)0.0009 (15)0.0255 (16)0.0028 (15)
C110.0445 (18)0.050 (2)0.054 (2)0.0010 (14)0.0113 (16)0.0024 (16)
C120.056 (2)0.058 (2)0.0407 (19)0.0002 (16)0.0082 (16)0.0032 (15)
C130.104 (3)0.095 (3)0.0597 (19)0.008 (2)0.031 (2)0.006 (2)
C140.054 (2)0.055 (2)0.0513 (17)0.0061 (17)0.0174 (18)0.0000 (16)
C150.049 (2)0.054 (2)0.059 (2)0.0011 (16)0.0040 (17)0.0079 (16)
C160.0452 (19)0.055 (2)0.062 (2)0.0006 (15)0.0197 (17)0.0003 (17)
C170.056 (2)0.049 (2)0.048 (2)0.0065 (16)0.0157 (18)0.0015 (16)
C180.0452 (19)0.060 (2)0.057 (2)0.0002 (16)0.0069 (16)0.0016 (17)
C190.050 (2)0.066 (2)0.064 (2)0.0027 (17)0.0236 (17)0.0055 (18)
C200.096 (3)0.099 (3)0.072 (2)0.012 (2)0.048 (2)0.0015 (19)
C210.097 (3)0.119 (3)0.048 (2)0.005 (2)0.0117 (19)0.005 (2)
C220.086 (3)0.075 (3)0.062 (3)0.008 (2)0.029 (2)0.006 (2)
C230.058 (2)0.051 (2)0.048 (2)0.0055 (17)0.0167 (17)0.0034 (15)
C240.053 (2)0.048 (2)0.054 (2)0.0001 (15)0.0065 (16)0.0027 (16)
C250.049 (2)0.056 (2)0.058 (2)0.0012 (15)0.0215 (17)0.0003 (16)
C260.054 (2)0.047 (2)0.0440 (19)0.0023 (16)0.0107 (17)0.0012 (15)
C270.0470 (19)0.054 (2)0.057 (2)0.0048 (15)0.0098 (16)0.0022 (16)
C280.054 (2)0.056 (2)0.066 (2)0.0014 (16)0.0256 (18)0.0063 (18)
C290.097 (3)0.098 (3)0.058 (2)0.000 (2)0.040 (2)0.0065 (19)
C300.089 (2)0.112 (3)0.046 (2)0.012 (2)0.0060 (18)0.0040 (19)
Geometric parameters (Å, º) top
N1—C11.329 (3)C10—C111.398 (3)
N1—H1A0.8600C11—C121.350 (3)
N1—H1B0.8600C11—H110.9300
N2—O21.233 (3)C12—H120.9300
N2—O11.236 (3)C13—C141.441 (4)
N2—C21.441 (3)C13—H130.9300
N3—O41.223 (3)C14—C191.379 (3)
N3—O31.235 (3)C14—C151.387 (3)
N3—C41.450 (3)C15—C161.364 (3)
N4—C71.329 (3)C15—H150.9300
N4—H4A0.8600C16—C171.397 (3)
N4—H4B0.8600C16—H160.9300
N5—O61.226 (3)C17—C181.410 (3)
N5—O51.242 (3)C18—C191.366 (3)
N5—C81.437 (3)C18—H180.9300
N6—O81.217 (2)C19—H190.9300
N6—O71.233 (2)C20—H20A0.9600
N6—C101.450 (3)C20—H20B0.9600
N7—C171.351 (3)C20—H20C0.9600
N7—C201.451 (3)C21—H21A0.9600
N7—C211.453 (3)C21—H21B0.9600
N8—C261.362 (3)C21—H21C0.9600
N8—C291.448 (3)C22—C231.451 (4)
N8—C301.465 (3)C22—H220.9300
O9—C131.204 (3)C23—C281.384 (3)
O10—C221.207 (3)C23—C241.389 (3)
C1—C61.405 (3)C24—C251.365 (3)
C1—C21.413 (3)C24—H240.9300
C2—C31.386 (3)C25—C261.405 (3)
C3—C41.352 (3)C25—H250.9300
C3—H30.9300C26—C271.403 (3)
C4—C51.392 (3)C27—C281.365 (3)
C5—C61.352 (3)C27—H270.9300
C5—H50.9300C28—H280.9300
C6—H60.9300C29—H29A0.9600
C7—C121.406 (3)C29—H29B0.9600
C7—C81.413 (3)C29—H29C0.9600
C8—C91.377 (3)C30—H30A0.9600
C9—C101.350 (3)C30—H30B0.9600
C9—H90.9300C30—H30C0.9600
C1—N1—H1A120.0C19—C14—C15118.1 (3)
C1—N1—H1B120.0C19—C14—C13121.5 (3)
H1A—N1—H1B120.0C15—C14—C13120.4 (3)
O2—N2—O1122.3 (3)C16—C15—C14121.2 (3)
O2—N2—C2118.8 (3)C16—C15—H15119.4
O1—N2—C2118.9 (3)C14—C15—H15119.4
O4—N3—O3123.2 (3)C15—C16—C17121.5 (3)
O4—N3—C4118.5 (3)C15—C16—H16119.3
O3—N3—C4118.3 (3)C17—C16—H16119.3
C7—N4—H4A120.0N7—C17—C16121.8 (3)
C7—N4—H4B120.0N7—C17—C18121.3 (3)
H4A—N4—H4B120.0C16—C17—C18116.9 (3)
O6—N5—O5121.8 (3)C19—C18—C17120.9 (3)
O6—N5—C8119.0 (3)C19—C18—H18119.6
O5—N5—C8119.2 (3)C17—C18—H18119.6
O8—N6—O7122.6 (3)C18—C19—C14121.6 (3)
O8—N6—C10119.0 (3)C18—C19—H19119.2
O7—N6—C10118.4 (3)C14—C19—H19119.2
C17—N7—C20121.5 (3)N7—C20—H20A109.5
C17—N7—C21121.8 (3)N7—C20—H20B109.5
C20—N7—C21116.7 (3)H20A—C20—H20B109.5
C26—N8—C29122.4 (3)N7—C20—H20C109.5
C26—N8—C30120.9 (2)H20A—C20—H20C109.5
C29—N8—C30116.6 (2)H20B—C20—H20C109.5
N1—C1—C6118.8 (3)N7—C21—H21A109.5
N1—C1—C2124.9 (3)N7—C21—H21B109.5
C6—C1—C2116.3 (3)H21A—C21—H21B109.5
C3—C2—C1120.7 (3)N7—C21—H21C109.5
C3—C2—N2117.0 (3)H21A—C21—H21C109.5
C1—C2—N2122.3 (3)H21B—C21—H21C109.5
C4—C3—C2120.1 (2)O10—C22—C23126.9 (3)
C4—C3—H3119.9O10—C22—H22116.6
C2—C3—H3119.9C23—C22—H22116.6
C3—C4—C5121.0 (3)C28—C23—C24118.1 (3)
C3—C4—N3119.8 (3)C28—C23—C22121.8 (3)
C5—C4—N3119.2 (3)C24—C23—C22120.1 (3)
C6—C5—C4119.1 (3)C25—C24—C23121.2 (3)
C6—C5—H5120.5C25—C24—H24119.4
C4—C5—H5120.5C23—C24—H24119.4
C5—C6—C1122.7 (3)C24—C25—C26121.0 (3)
C5—C6—H6118.7C24—C25—H25119.5
C1—C6—H6118.7C26—C25—H25119.5
N4—C7—C12118.6 (3)N8—C26—C27121.8 (3)
N4—C7—C8124.8 (3)N8—C26—C25120.8 (3)
C12—C7—C8116.6 (3)C27—C26—C25117.4 (3)
C9—C8—C7120.8 (3)C28—C27—C26120.8 (3)
C9—C8—N5117.1 (2)C28—C27—H27119.6
C7—C8—N5122.1 (3)C26—C27—H27119.6
C10—C9—C8120.1 (3)C27—C28—C23121.6 (3)
C10—C9—H9120.0C27—C28—H28119.2
C8—C9—H9120.0C23—C28—H28119.2
C9—C10—C11121.3 (3)N8—C29—H29A109.5
C9—C10—N6120.1 (3)N8—C29—H29B109.5
C11—C10—N6118.6 (3)H29A—C29—H29B109.5
C12—C11—C10118.7 (3)N8—C29—H29C109.5
C12—C11—H11120.6H29A—C29—H29C109.5
C10—C11—H11120.6H29B—C29—H29C109.5
C11—C12—C7122.4 (3)N8—C30—H30A109.5
C11—C12—H12118.8N8—C30—H30B109.5
C7—C12—H12118.8H30A—C30—H30B109.5
O9—C13—C14126.4 (4)N8—C30—H30C109.5
O9—C13—H13116.8H30A—C30—H30C109.5
C14—C13—H13116.8H30B—C30—H30C109.5
N1—C1—C2—C3179.8 (2)C9—C10—C11—C120.8 (4)
C6—C1—C2—C30.4 (4)N6—C10—C11—C12178.0 (2)
N1—C1—C2—N20.0 (4)C10—C11—C12—C70.2 (4)
C6—C1—C2—N2179.8 (2)N4—C7—C12—C11179.8 (2)
O2—N2—C2—C30.1 (4)C8—C7—C12—C110.4 (4)
O1—N2—C2—C3179.3 (2)O9—C13—C14—C19173.6 (3)
O2—N2—C2—C1179.9 (3)O9—C13—C14—C154.0 (5)
O1—N2—C2—C10.9 (4)C19—C14—C15—C160.3 (4)
C1—C2—C3—C40.0 (4)C13—C14—C15—C16177.9 (3)
N2—C2—C3—C4179.9 (2)C14—C15—C16—C171.2 (4)
C2—C3—C4—C50.3 (4)C20—N7—C17—C161.3 (4)
C2—C3—C4—N3179.0 (2)C21—N7—C17—C16179.0 (3)
O4—N3—C4—C3179.0 (3)C20—N7—C17—C18179.9 (3)
O3—N3—C4—C30.2 (4)C21—N7—C17—C182.1 (4)
O4—N3—C4—C50.4 (4)C15—C16—C17—N7177.7 (3)
O3—N3—C4—C5179.2 (3)C15—C16—C17—C181.2 (4)
C3—C4—C5—C60.3 (4)N7—C17—C18—C19178.5 (3)
N3—C4—C5—C6179.0 (2)C16—C17—C18—C190.4 (4)
C4—C5—C6—C10.1 (4)C17—C18—C19—C140.4 (4)
N1—C1—C6—C5179.7 (2)C15—C14—C19—C180.5 (4)
C2—C1—C6—C50.4 (4)C13—C14—C19—C18177.1 (3)
N4—C7—C8—C9179.9 (2)O10—C22—C23—C28174.9 (3)
C12—C7—C8—C90.3 (4)O10—C22—C23—C243.2 (5)
N4—C7—C8—N51.5 (4)C28—C23—C24—C250.7 (4)
C12—C7—C8—N5178.7 (2)C22—C23—C24—C25178.8 (2)
O6—N5—C8—C91.9 (4)C23—C24—C25—C261.9 (4)
O5—N5—C8—C9177.4 (3)C29—N8—C26—C27177.7 (3)
O6—N5—C8—C7179.6 (3)C30—N8—C26—C270.7 (4)
O5—N5—C8—C71.1 (4)C29—N8—C26—C253.2 (4)
C7—C8—C9—C100.3 (4)C30—N8—C26—C25179.8 (2)
N5—C8—C9—C10178.2 (2)C24—C25—C26—N8178.6 (3)
C8—C9—C10—C110.9 (4)C24—C25—C26—C272.2 (4)
C8—C9—C10—N6177.9 (2)N8—C26—C27—C28179.4 (2)
O8—N6—C10—C9172.5 (3)C25—C26—C27—C281.4 (4)
O7—N6—C10—C97.5 (4)C26—C27—C28—C230.3 (4)
O8—N6—C10—C116.3 (4)C24—C23—C28—C270.1 (4)
O7—N6—C10—C11173.7 (3)C22—C23—C28—C27178.0 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1A···O10i0.862.183.010 (3)163
N1—H1B···O10.862.032.640 (3)127
N1—H1B···O7ii0.862.493.170 (3)136
N4—H4A···O9iii0.862.042.889 (3)171
N4—H4B···O50.862.022.636 (3)128
N4—H4B···O3iii0.862.423.047 (3)130
Symmetry codes: (i) x1/2, y+1/2, z+1/2; (ii) x+1/2, y1/2, z+3/2; (iii) x+1, y+1, z+1.

Experimental details

Crystal data
Chemical formulaC9H11NO·C6H5N3O4
Mr332.32
Crystal system, space groupMonoclinic, P21/n
Temperature (K)298
a, b, c (Å)18.7512 (18), 7.3182 (6), 24.338 (2)
β (°) 109.493 (1)
V3)3148.4 (5)
Z8
Radiation typeMo Kα
µ (mm1)0.11
Crystal size (mm)0.48 × 0.18 × 0.11
Data collection
DiffractometerBruker SMART CCD
diffractometer
Absorption correctionMulti-scan
(SADABS; Bruker, 2007)
Tmin, Tmax0.950, 0.988
No. of measured, independent and
observed [I > 2σ(I)] reflections
15396, 5547, 2303
Rint0.060
(sin θ/λ)max1)0.595
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.048, 0.087, 1.02
No. of reflections5547
No. of parameters433
No. of restraints6
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.17, 0.20

Computer programs: SMART (Bruker, 2007), SAINT (Bruker, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1A···O10i0.862.183.010 (3)163
N1—H1B···O10.862.032.640 (3)127
N1—H1B···O7ii0.862.493.170 (3)136
N4—H4A···O9iii0.862.042.889 (3)171
N4—H4B···O50.862.022.636 (3)128
N4—H4B···O3iii0.862.423.047 (3)130
Symmetry codes: (i) x1/2, y+1/2, z+1/2; (ii) x+1/2, y1/2, z+3/2; (iii) x+1, y+1, z+1.
 

Acknowledgements

The authors gratefully acknowledge the University Technology Development Project in Shanxi Province (grant Nos. 20091144 and 20101116).

References

First citationAllen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1–19.  CrossRef Web of Science Google Scholar
First citationBruker (2007). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.  Google Scholar
First citationNesterov, V. N., Timofeeva, T. V., Antipin, M. Y. & Clark, R. D. (2000). Acta Cryst. C56, 976–978.  Web of Science CSD CrossRef CAS IUCr Journals Google Scholar
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
First citationSpek, A. L. (2009). Acta Cryst. D65, 148–155.  Web of Science CrossRef CAS IUCr Journals Google Scholar
First citationWeber, G. & Sheldrick, G. M. (1981). Acta Cryst. B37, 2108–2111.  CSD CrossRef CAS Web of Science IUCr Journals Google Scholar

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