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

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ISSN: 2056-9890

N-{2-[2-(2-Cyano-4,6-di­nitro­phen­yl)diazen­yl]-5-(di­ethyl­amino)phen­yl}acetamide

aCollege of Chemistry and Pharmaceutical Sciences, Qingdao Agricultural University, Qingdao 266109, People's Republic of China
*Correspondence e-mail: lhedlut2002@yahoo.com.cn

(Received 22 July 2012; accepted 20 September 2012; online 26 September 2012)

The title compound, C19H19N7O5, exhibits substitutional disorder of the ortho-nitro and cyano groups, with site-occupancy factors of 0.686 (7):0.314 (7). The two aromatic rings are essentially coplanar, with a dihedral angle of 6.6 (5)°. In the diethyl­amino group, the two ethyl groups lie on the same side of the amino­benzene plane. An intra­molecular N—H⋯N hydrogen bond links the amino and diazenyl groups.

Related literature

For the influence of the substitutent on molecular planarity, see: Freeman et al. (1997[Freeman, H. S., McIntosh, S. A. & Singh, P. (1997). Dyes Pigm. 35, 149-164.]); Lu & He (2012[Lu, L. & He, L. (2012). J. Mol. Struct. 1010, 79-84.]). For similar structures, see: Gong & Lu (2011[Gong, L. & Lu, L. (2011). Acta Cryst. E67, o662.]); He et al. (2009[He, L., El-Shafei, A., Freeman, H. S. & Boyle, P. (2009). Dyes Pigm. 82, 299-306.]).

[Scheme 1]

Experimental

Crystal data
  • C19H19N7O5

  • Mr = 425.41

  • Monoclinic, P 21 /c

  • a = 5.0995 (5) Å

  • b = 30.792 (3) Å

  • c = 12.7211 (11) Å

  • β = 93.569 (1)°

  • V = 1993.6 (3) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 0.11 mm−1

  • T = 298 K

  • 0.37 × 0.11 × 0.07 mm

Data collection
  • Bruker SMART CCD area-detector diffractometer

  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996[Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.]) Tmin = 0.962, Tmax = 0.993

  • 10384 measured reflections

  • 3487 independent reflections

  • 1453 reflections with I > 2σ(I)

  • Rint = 0.108

Refinement
  • R[F2 > 2σ(F2)] = 0.067

  • wR(F2) = 0.157

  • S = 1.00

  • 3487 reflections

  • 311 parameters

  • H-atom parameters constrained

  • Δρmax = 0.20 e Å−3

  • Δρmin = −0.19 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
N3—H3⋯N2 0.86 2.01 2.676 (4) 133

Data collection: SMART (Siemens, 1996[Siemens (1996). SMART and SAINT. Siemens Analytical X-ray Instruments Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Siemens, 1996[Siemens (1996). SMART and SAINT. Siemens Analytical X-ray Instruments 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: ORTEP-3 (Farrugia, 1997[Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.]); software used to prepare material for publication: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]).

Supporting information


Comment top

It is well known that technical properties and functionalities of chemcial compounds are often related to their molecular structures and their inter/intra-molecular interactions in crystalline state. Hence, the structural investigation of different compounds in solid state is very important.

The title compound, C19H19N7O5, exhibits substitutional disorder of the nitro group at 2'-position and the cyano group at 6'-position, with site-occupancy factors of 0.686 (7): 0.314 (7). The main position of the disordered nitro group is close to the acetylamino group. The two aromatic rings are essentially coplanar, although they have a dihedral angle of 6.6 (5) °. In the N,N-diethylamino group at 4-positon, two ethyl chains tend to stand on the same side of the aminobenzene plane. The intramolecular N—H···N hydrogen bond links the amino and azo groups. (Table 1).

Related literature top

For related background [on what subject?], see: Freeman et al. (1997); Lu & He (2012). For similar structures, see: Gong & Lu (2011); He et al. (2009).

Experimental top

The crystals were obtained by dissolving 0.1 g of the title compound in 20 ml of acetone at room temperature and the resulting solution was covered with Parafilm plastic containing pin holes for slow evaporation of the solvent.

Refinement top

The nitro group at 2'-position and the cyano group at 6'-position are disordered over two sites with a refined site-occupancy factors of 0.686 (7): 0.314 (7). All hydrogen atoms were placed in their calculated positions, with N—H = 0.86 Å, and C—H = 0.93 or 0.96 Å, and refined using a riding model, with Uiso = 1.2 Ueq (N) and Uiso = 1.2 or 1.5 Ueq (C).

Structure description top

It is well known that technical properties and functionalities of chemcial compounds are often related to their molecular structures and their inter/intra-molecular interactions in crystalline state. Hence, the structural investigation of different compounds in solid state is very important.

The title compound, C19H19N7O5, exhibits substitutional disorder of the nitro group at 2'-position and the cyano group at 6'-position, with site-occupancy factors of 0.686 (7): 0.314 (7). The main position of the disordered nitro group is close to the acetylamino group. The two aromatic rings are essentially coplanar, although they have a dihedral angle of 6.6 (5) °. In the N,N-diethylamino group at 4-positon, two ethyl chains tend to stand on the same side of the aminobenzene plane. The intramolecular N—H···N hydrogen bond links the amino and azo groups. (Table 1).

For related background [on what subject?], see: Freeman et al. (1997); Lu & He (2012). For similar structures, see: Gong & Lu (2011); He et al. (2009).

Computing details top

Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT (Siemens, 1996); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. ORTEP drawing of 2-acetylamino-4-(N,N-diethylamino)-2',4'-dinitro-6'-cyanoazobenzene.
N-{2-[2-(2-Cyano-4,6-dinitrophenyl)diazenyl]- 5-(diethylamino)phenyl}acetamide top
Crystal data top
C19H19N7O5F(000) = 888
Mr = 425.41Dx = 1.417 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 1060 reflections
a = 5.0995 (5) Åθ = 2.7–26.4°
b = 30.792 (3) ŵ = 0.11 mm1
c = 12.7211 (11) ÅT = 298 K
β = 93.569 (1)°Prism, blue
V = 1993.6 (3) Å30.37 × 0.11 × 0.07 mm
Z = 4
Data collection top
Bruker SMART CCD area-detector
diffractometer
3487 independent reflections
Radiation source: fine-focus sealed tube1453 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.108
φ and ω scansθmax = 25.0°, θmin = 2.6°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 66
Tmin = 0.962, Tmax = 0.993k = 3536
10384 measured reflectionsl = 1512
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)] = 0.067Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.157H-atom parameters constrained
S = 1.00 w = 1/[σ2(Fo2) + (0.0376P)2]
where P = (Fo2 + 2Fc2)/3
3487 reflections(Δ/σ)max = 0.001
311 parametersΔρmax = 0.20 e Å3
0 restraintsΔρmin = 0.19 e Å3
Crystal data top
C19H19N7O5V = 1993.6 (3) Å3
Mr = 425.41Z = 4
Monoclinic, P21/cMo Kα radiation
a = 5.0995 (5) ŵ = 0.11 mm1
b = 30.792 (3) ÅT = 298 K
c = 12.7211 (11) Å0.37 × 0.11 × 0.07 mm
β = 93.569 (1)°
Data collection top
Bruker SMART CCD area-detector
diffractometer
3487 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
1453 reflections with I > 2σ(I)
Tmin = 0.962, Tmax = 0.993Rint = 0.108
10384 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0670 restraints
wR(F2) = 0.157H-atom parameters constrained
S = 1.00Δρmax = 0.20 e Å3
3487 reflectionsΔρmin = 0.19 e Å3
311 parameters
Special details top

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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*/UeqOcc. (<1)
N10.4053 (6)0.60751 (10)0.4507 (2)0.0579 (9)
N20.5520 (6)0.63947 (10)0.4218 (2)0.0576 (9)
N30.3410 (6)0.69052 (10)0.5644 (2)0.0574 (9)
H30.46950.68630.52490.069*
N40.2983 (6)0.61740 (10)0.7645 (2)0.0557 (9)
N50.8292 (11)0.70338 (16)0.3319 (4)0.0671 (14)0.686 (7)
C19'0.8292 (11)0.70338 (16)0.3319 (4)0.0671 (14)0.314 (7)
N61.2621 (8)0.59919 (14)0.1118 (3)0.0658 (10)
N70.507 (2)0.5147 (3)0.3559 (8)0.091 (3)0.686 (7)
N7'0.861 (6)0.7323 (10)0.367 (2)0.100 (8)0.314 (7)
O10.1396 (6)0.74446 (9)0.6539 (2)0.0863 (10)
O20.6223 (11)0.72310 (15)0.3001 (4)0.0819 (19)0.686 (7)
O30.9997 (16)0.7223 (4)0.3842 (9)0.096 (3)0.686 (7)
O2'0.410 (2)0.5311 (5)0.2877 (9)0.079 (4)0.314 (7)
O3'0.697 (3)0.5215 (4)0.4102 (9)0.089 (4)0.314 (7)
O41.4090 (6)0.62839 (10)0.0872 (2)0.0829 (10)
O51.2586 (7)0.56315 (12)0.0723 (3)0.1043 (12)
C10.2380 (8)0.61505 (12)0.5298 (3)0.0485 (10)
C20.1973 (7)0.65404 (12)0.5871 (3)0.0500 (10)
C30.0152 (8)0.65415 (13)0.6638 (3)0.0567 (11)
H3A0.01350.67970.70030.068*
C40.1276 (8)0.61654 (13)0.6879 (3)0.0526 (10)
C50.0889 (8)0.57806 (13)0.6280 (3)0.0596 (11)
H50.18530.55310.64010.071*
C60.0887 (8)0.57827 (13)0.5538 (3)0.0583 (11)
H60.11400.55280.51650.070*
C70.3066 (9)0.73243 (14)0.5963 (4)0.0672 (12)
C80.4882 (9)0.76442 (13)0.5484 (4)0.0805 (14)
H8A0.45240.76520.47350.121*
H8B0.66710.75570.56420.121*
H8C0.46080.79280.57710.121*
C90.4391 (8)0.57792 (14)0.7952 (3)0.0706 (13)
H9A0.48960.56150.73210.085*
H9B0.59900.58660.82700.085*
C100.2868 (11)0.54915 (15)0.8696 (4)0.0994 (17)
H10A0.12650.54070.83950.149*
H10B0.38860.52380.88310.149*
H10C0.24650.56440.93450.149*
C110.3232 (8)0.65583 (13)0.8310 (3)0.0612 (11)
H11A0.48930.65440.86400.073*
H11B0.32650.68150.78680.073*
C120.1039 (9)0.66039 (14)0.9157 (3)0.0769 (13)
H12A0.10420.63570.96180.115*
H12B0.12970.68640.95540.115*
H12C0.06140.66200.88370.115*
C130.7156 (8)0.62571 (13)0.3432 (3)0.0499 (10)
C140.8682 (8)0.65840 (13)0.3000 (3)0.0521 (10)
C151.0444 (8)0.65038 (14)0.2260 (3)0.0585 (11)
H151.14510.67280.20060.070*
C161.0710 (8)0.60897 (13)0.1897 (3)0.0549 (11)
C170.9265 (8)0.57544 (14)0.2275 (3)0.0620 (12)
H170.94790.54730.20260.074*
C180.7464 (8)0.58378 (13)0.3040 (3)0.0539 (11)
C190.6071 (11)0.54535 (17)0.3394 (4)0.0660 (13)0.686 (7)
N5'0.6071 (11)0.54535 (17)0.3394 (4)0.0660 (13)0.314 (7)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N10.047 (2)0.064 (2)0.062 (2)0.0022 (18)0.0040 (19)0.0079 (17)
N20.049 (2)0.057 (2)0.067 (2)0.0032 (18)0.0078 (18)0.0001 (17)
N30.044 (2)0.055 (2)0.076 (2)0.0024 (17)0.0234 (18)0.0031 (17)
N40.040 (2)0.058 (2)0.071 (2)0.0015 (17)0.0138 (18)0.0028 (18)
N50.064 (4)0.064 (3)0.074 (3)0.009 (3)0.017 (3)0.010 (2)
C19'0.064 (4)0.064 (3)0.074 (3)0.009 (3)0.017 (3)0.010 (2)
N60.063 (3)0.073 (3)0.063 (3)0.014 (2)0.020 (2)0.001 (2)
N70.102 (8)0.076 (6)0.098 (7)0.011 (6)0.025 (6)0.007 (5)
N7'0.11 (3)0.087 (18)0.106 (17)0.003 (16)0.014 (19)0.014 (12)
O10.073 (2)0.068 (2)0.123 (3)0.0030 (17)0.052 (2)0.0156 (18)
O20.067 (4)0.067 (3)0.112 (4)0.025 (3)0.009 (3)0.003 (3)
O30.078 (7)0.091 (6)0.116 (5)0.001 (5)0.021 (5)0.022 (4)
O2'0.066 (9)0.094 (9)0.075 (9)0.006 (7)0.013 (6)0.001 (7)
O3'0.088 (11)0.080 (8)0.097 (10)0.002 (7)0.001 (7)0.035 (7)
O40.066 (2)0.088 (2)0.099 (2)0.0012 (18)0.0371 (19)0.0119 (18)
O50.112 (3)0.088 (3)0.120 (3)0.001 (2)0.060 (2)0.023 (2)
C10.041 (3)0.054 (2)0.052 (3)0.004 (2)0.011 (2)0.001 (2)
C20.036 (3)0.053 (3)0.062 (3)0.004 (2)0.007 (2)0.007 (2)
C30.046 (3)0.059 (3)0.066 (3)0.004 (2)0.009 (2)0.003 (2)
C40.037 (3)0.060 (3)0.061 (3)0.001 (2)0.006 (2)0.003 (2)
C50.051 (3)0.062 (3)0.067 (3)0.010 (2)0.014 (2)0.002 (2)
C60.054 (3)0.058 (3)0.064 (3)0.003 (2)0.008 (2)0.001 (2)
C70.054 (3)0.064 (3)0.085 (3)0.005 (3)0.019 (3)0.006 (2)
C80.069 (3)0.067 (3)0.109 (4)0.012 (3)0.037 (3)0.004 (2)
C90.053 (3)0.074 (3)0.088 (3)0.008 (2)0.027 (3)0.001 (3)
C100.122 (5)0.080 (4)0.097 (4)0.006 (3)0.015 (3)0.019 (3)
C110.045 (3)0.061 (3)0.080 (3)0.005 (2)0.025 (2)0.002 (2)
C120.060 (3)0.084 (3)0.086 (3)0.004 (3)0.005 (3)0.016 (2)
C130.045 (3)0.057 (3)0.048 (3)0.004 (2)0.004 (2)0.005 (2)
C140.043 (3)0.057 (3)0.057 (3)0.003 (2)0.007 (2)0.004 (2)
C150.048 (3)0.068 (3)0.060 (3)0.001 (2)0.008 (2)0.004 (2)
C160.052 (3)0.058 (3)0.057 (3)0.001 (2)0.012 (2)0.000 (2)
C170.056 (3)0.065 (3)0.066 (3)0.003 (2)0.011 (2)0.004 (2)
C180.046 (3)0.059 (3)0.057 (3)0.005 (2)0.006 (2)0.007 (2)
C190.059 (4)0.069 (3)0.070 (4)0.000 (3)0.013 (3)0.000 (3)
N5'0.059 (4)0.069 (3)0.070 (4)0.000 (3)0.013 (3)0.000 (3)
Geometric parameters (Å, º) top
N1—N21.303 (4)C7—C81.506 (5)
N1—C11.379 (4)C8—H8A0.9600
N2—C131.407 (4)C8—H8B0.9600
N3—C71.367 (5)C8—H8C0.9600
N3—C21.382 (4)C9—C101.481 (6)
N3—H30.8600C9—H9A0.9700
N4—C41.347 (4)C9—H9B0.9700
N4—C111.465 (4)C10—H10A0.9600
N4—C91.477 (5)C10—H10B0.9600
N5—O31.211 (12)C10—H10C0.9600
N5—O21.262 (7)C11—C121.510 (5)
N5—C141.460 (6)C11—H11A0.9700
N6—O51.218 (4)C11—H11B0.9700
N6—O41.224 (4)C12—H12A0.9600
N6—C161.464 (5)C12—H12B0.9600
N7—C191.099 (8)C12—H12C0.9600
O1—C71.215 (4)C13—C181.396 (5)
C1—C61.409 (5)C13—C141.405 (5)
C1—C21.426 (5)C14—C151.364 (5)
C2—C31.388 (5)C15—C161.366 (5)
C3—C41.412 (5)C15—H150.9300
C3—H3A0.9300C16—C171.373 (5)
C4—C51.429 (5)C17—C181.403 (5)
C5—C61.349 (5)C17—H170.9300
C5—H50.9300C18—C191.465 (6)
C6—H60.9300
N2—N1—C1118.1 (3)N4—C9—H9A108.6
N1—N2—C13110.4 (3)C10—C9—H9A108.6
C7—N3—C2128.8 (3)N4—C9—H9B108.6
C7—N3—H3115.6C10—C9—H9B108.6
C2—N3—H3115.6H9A—C9—H9B107.6
C4—N4—C11121.1 (3)C9—C10—H10A109.5
C4—N4—C9121.4 (3)C9—C10—H10B109.5
C11—N4—C9116.8 (3)H10A—C10—H10B109.5
O3—N5—O2120.2 (8)C9—C10—H10C109.5
O3—N5—C14120.2 (7)H10A—C10—H10C109.5
O2—N5—C14119.5 (5)H10B—C10—H10C109.5
O5—N6—O4123.9 (4)N4—C11—C12113.6 (3)
O5—N6—C16118.3 (4)N4—C11—H11A108.8
O4—N6—C16117.8 (4)C12—C11—H11A108.8
N1—C1—C6113.0 (3)N4—C11—H11B108.8
N1—C1—C2129.1 (3)C12—C11—H11B108.8
C6—C1—C2117.9 (4)H11A—C11—H11B107.7
N3—C2—C3122.1 (3)C11—C12—H12A109.5
N3—C2—C1118.8 (3)C11—C12—H12B109.5
C3—C2—C1119.1 (3)H12A—C12—H12B109.5
C2—C3—C4121.8 (4)C11—C12—H12C109.5
C2—C3—H3A119.1H12A—C12—H12C109.5
C4—C3—H3A119.1H12B—C12—H12C109.5
N4—C4—C3120.4 (4)C18—C13—C14116.4 (4)
N4—C4—C5121.3 (4)C18—C13—N2128.1 (4)
C3—C4—C5118.3 (4)C14—C13—N2115.5 (3)
C6—C5—C4119.4 (4)C15—C14—C13123.1 (4)
C6—C5—H5120.3C15—C14—N5118.1 (4)
C4—C5—H5120.3C13—C14—N5118.8 (4)
C5—C6—C1123.4 (4)C14—C15—C16119.0 (4)
C5—C6—H6118.3C14—C15—H15120.5
C1—C6—H6118.3C16—C15—H15120.5
O1—C7—N3125.0 (4)C15—C16—C17121.1 (4)
O1—C7—C8121.1 (4)C15—C16—N6120.3 (4)
N3—C7—C8113.8 (4)C17—C16—N6118.5 (4)
C7—C8—H8A109.5C16—C17—C18119.6 (4)
C7—C8—H8B109.5C16—C17—H17120.2
H8A—C8—H8B109.5C18—C17—H17120.2
C7—C8—H8C109.5C13—C18—C17120.7 (4)
H8A—C8—H8C109.5C13—C18—C19124.7 (4)
H8B—C8—H8C109.5C17—C18—C19114.6 (4)
N4—C9—C10114.7 (4)N7—C19—C18172.6 (7)
C1—N1—N2—C13178.1 (3)C9—N4—C11—C1294.0 (4)
N2—N1—C1—C6179.7 (3)N1—N2—C13—C185.6 (5)
N2—N1—C1—C20.4 (6)N1—N2—C13—C14175.2 (3)
C7—N3—C2—C311.5 (6)C18—C13—C14—C152.0 (6)
C7—N3—C2—C1168.6 (4)N2—C13—C14—C15177.4 (4)
N1—C1—C2—N30.5 (6)C18—C13—C14—N5175.3 (4)
C6—C1—C2—N3179.7 (4)N2—C13—C14—N55.4 (6)
N1—C1—C2—C3179.6 (4)O3—N5—C14—C1570.7 (8)
C6—C1—C2—C30.4 (5)O2—N5—C14—C15105.7 (5)
N3—C2—C3—C4178.8 (3)O3—N5—C14—C13111.9 (7)
C1—C2—C3—C41.1 (6)O2—N5—C14—C1371.7 (6)
C11—N4—C4—C35.6 (6)C13—C14—C15—C161.7 (6)
C9—N4—C4—C3176.6 (4)N5—C14—C15—C16175.6 (4)
C11—N4—C4—C5175.4 (4)C14—C15—C16—C171.0 (6)
C9—N4—C4—C54.4 (6)C14—C15—C16—N6178.8 (4)
C2—C3—C4—N4178.4 (4)O5—N6—C16—C15171.5 (4)
C2—C3—C4—C52.6 (6)O4—N6—C16—C155.6 (6)
N4—C4—C5—C6178.4 (4)O5—N6—C16—C1710.6 (6)
C3—C4—C5—C62.6 (6)O4—N6—C16—C17172.3 (4)
C4—C5—C6—C11.2 (6)C15—C16—C17—C180.6 (6)
N1—C1—C6—C5179.6 (4)N6—C16—C17—C18178.5 (4)
C2—C1—C6—C50.3 (6)C14—C13—C18—C171.6 (6)
C2—N3—C7—O11.6 (7)N2—C13—C18—C17177.7 (4)
C2—N3—C7—C8175.1 (4)C14—C13—C18—C19179.5 (4)
C4—N4—C9—C1082.3 (5)N2—C13—C18—C190.3 (7)
C11—N4—C9—C1089.0 (5)C16—C17—C18—C131.0 (6)
C4—N4—C11—C1277.3 (5)C16—C17—C18—C19179.1 (4)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N3—H3···N20.862.012.676 (4)133

Experimental details

Crystal data
Chemical formulaC19H19N7O5
Mr425.41
Crystal system, space groupMonoclinic, P21/c
Temperature (K)298
a, b, c (Å)5.0995 (5), 30.792 (3), 12.7211 (11)
β (°) 93.569 (1)
V3)1993.6 (3)
Z4
Radiation typeMo Kα
µ (mm1)0.11
Crystal size (mm)0.37 × 0.11 × 0.07
Data collection
DiffractometerBruker SMART CCD area-detector
Absorption correctionMulti-scan
(SADABS; Sheldrick, 1996)
Tmin, Tmax0.962, 0.993
No. of measured, independent and
observed [I > 2σ(I)] reflections
10384, 3487, 1453
Rint0.108
(sin θ/λ)max1)0.595
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.067, 0.157, 1.00
No. of reflections3487
No. of parameters311
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.20, 0.19

Computer programs: SMART (Siemens, 1996), SAINT (Siemens, 1996), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N3—H3···N20.862.0112.676 (4)133.41
 

References

First citationFarrugia, L. J. (1997). J. Appl. Cryst. 30, 565.  CrossRef IUCr Journals Google Scholar
First citationFreeman, H. S., McIntosh, S. A. & Singh, P. (1997). Dyes Pigm. 35, 149–164.  CrossRef CAS Web of Science Google Scholar
First citationGong, L. & Lu, L. (2011). Acta Cryst. E67, o662.  Web of Science CSD CrossRef IUCr Journals Google Scholar
First citationHe, L., El-Shafei, A., Freeman, H. S. & Boyle, P. (2009). Dyes Pigm. 82, 299–306.  Web of Science CSD CrossRef CAS Google Scholar
First citationLu, L. & He, L. (2012). J. Mol. Struct. 1010, 79–84.  Web of Science CSD CrossRef CAS Google Scholar
First citationSheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.  Google Scholar
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
First citationSiemens (1996). SMART and SAINT. Siemens Analytical X-ray Instruments Inc., Madison, Wisconsin, USA.  Google Scholar

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