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

Lu, L.

doi:10.1107/S160053681203992X

organic compounds

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ISSN: 2056-9890

Volume 68| Part 10| October 2012| Page o3005

https://doi.org/10.1107/S160053681203992X

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

Lihua Lu ^a ^*

^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 ); Lu & He (2012 ). For similar structures, see: Gong & Lu (2011 ); He et al. (2009 ).

Experimental

Crystal data

C₁₉H₁₉N₇O₅
M_r = 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 ) T_min = 0.962, T_max = 0.993
10384 measured reflections
3487 independent reflections
1453 reflections with I > 2σ(I)
R_int = 0.108

Refinement

R[F² > 2σ(F²)] = 0.067
wR(F²) = 0.157
S = 1.00
3487 reflections
311 parameters
H-atom parameters constrained
Δρ_max = 0.20 e Å⁻³
Δρ_min = −0.19 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

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

Data collection: SMART (Siemens, 1996 ); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT; 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).

Supporting information

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S160053681203992X/aa2072sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S160053681203992X/aa2072Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S160053681203992X/aa2072Isup3.cml

checkCIF report

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.

Structure description 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).

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

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

C₁₉H₁₉N₇O₅	F(000) = 888
M_r = 425.41	D_x = 1.417 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 1060 reflections
a = 5.0995 (5) Å	θ = 2.7–26.4°
b = 30.792 (3) Å	µ = 0.11 mm⁻¹
c = 12.7211 (11) Å	T = 298 K
β = 93.569 (1)°	Prism, blue
V = 1993.6 (3) Å³	0.37 × 0.11 × 0.07 mm
Z = 4

Data collection top

Bruker SMART CCD area-detector diffractometer	3487 independent reflections
Radiation source: fine-focus sealed tube	1453 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.108
φ and ω scans	θ_max = 25.0°, θ_min = 2.6°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −6→6
T_min = 0.962, T_max = 0.993	k = −35→36
10384 measured reflections	l = −15→12

Refinement top

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)] = 0.067	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.157	H-atom parameters constrained
S = 1.00	w = 1/[σ²(F_o²) + (0.0376P)²] where P = (F_o² + 2F_c²)/3
3487 reflections	(Δ/σ)_max = 0.001
311 parameters	Δρ_max = 0.20 e Å⁻³
0 restraints	Δρ_min = −0.19 e Å⁻³

Crystal data top

C₁₉H₁₉N₇O₅	V = 1993.6 (3) Å³
M_r = 425.41	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 5.0995 (5) Å	µ = 0.11 mm⁻¹
b = 30.792 (3) Å	T = 298 K
c = 12.7211 (11) Å	0.37 × 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)
T_min = 0.962, T_max = 0.993	R_int = 0.108
10384 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.067	0 restraints
wR(F²) = 0.157	H-atom parameters constrained
S = 1.00	Δρ_max = 0.20 e Å⁻³
3487 reflections	Δρ_min = −0.19 e Å⁻³
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

	x	y	z	U_iso*/U_eq	Occ. (<1)
N1	0.4053 (6)	0.60751 (10)	0.4507 (2)	0.0579 (9)
N2	0.5520 (6)	0.63947 (10)	0.4218 (2)	0.0576 (9)
N3	0.3410 (6)	0.69052 (10)	0.5644 (2)	0.0574 (9)
H3	0.4695	0.6863	0.5249	0.069*
N4	−0.2983 (6)	0.61740 (10)	0.7645 (2)	0.0557 (9)
N5	0.8292 (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)
N6	1.2621 (8)	0.59919 (14)	0.1118 (3)	0.0658 (10)
N7	0.507 (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)
O1	0.1396 (6)	0.74446 (9)	0.6539 (2)	0.0863 (10)
O2	0.6223 (11)	0.72310 (15)	0.3001 (4)	0.0819 (19)	0.686 (7)
O3	0.9997 (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)
O4	1.4090 (6)	0.62839 (10)	0.0872 (2)	0.0829 (10)
O5	1.2586 (7)	0.56315 (12)	0.0723 (3)	0.1043 (12)
C1	0.2380 (8)	0.61505 (12)	0.5298 (3)	0.0485 (10)
C2	0.1973 (7)	0.65404 (12)	0.5871 (3)	0.0500 (10)
C3	0.0152 (8)	0.65415 (13)	0.6638 (3)	0.0567 (11)
H3A	−0.0135	0.6797	0.7003	0.068*
C4	−0.1276 (8)	0.61654 (13)	0.6879 (3)	0.0526 (10)
C5	−0.0889 (8)	0.57806 (13)	0.6280 (3)	0.0596 (11)
H5	−0.1853	0.5531	0.6401	0.071*
C6	0.0887 (8)	0.57827 (13)	0.5538 (3)	0.0583 (11)
H6	0.1140	0.5528	0.5165	0.070*
C7	0.3066 (9)	0.73243 (14)	0.5963 (4)	0.0672 (12)
C8	0.4882 (9)	0.76442 (13)	0.5484 (4)	0.0805 (14)
H8A	0.4524	0.7652	0.4735	0.121*
H8B	0.6671	0.7557	0.5642	0.121*
H8C	0.4608	0.7928	0.5771	0.121*
C9	−0.4391 (8)	0.57792 (14)	0.7952 (3)	0.0706 (13)
H9A	−0.4896	0.5615	0.7321	0.085*
H9B	−0.5990	0.5866	0.8270	0.085*
C10	−0.2868 (11)	0.54915 (15)	0.8696 (4)	0.0994 (17)
H10A	−0.1265	0.5407	0.8395	0.149*
H10B	−0.3886	0.5238	0.8831	0.149*
H10C	−0.2465	0.5644	0.9345	0.149*
C11	−0.3232 (8)	0.65583 (13)	0.8310 (3)	0.0612 (11)
H11A	−0.4893	0.6544	0.8640	0.073*
H11B	−0.3265	0.6815	0.7868	0.073*
C12	−0.1039 (9)	0.66039 (14)	0.9157 (3)	0.0769 (13)
H12A	−0.1042	0.6357	0.9618	0.115*
H12B	−0.1297	0.6864	0.9554	0.115*
H12C	0.0614	0.6620	0.8837	0.115*
C13	0.7156 (8)	0.62571 (13)	0.3432 (3)	0.0499 (10)
C14	0.8682 (8)	0.65840 (13)	0.3000 (3)	0.0521 (10)
C15	1.0444 (8)	0.65038 (14)	0.2260 (3)	0.0585 (11)
H15	1.1451	0.6728	0.2006	0.070*
C16	1.0710 (8)	0.60897 (13)	0.1897 (3)	0.0549 (11)
C17	0.9265 (8)	0.57544 (14)	0.2275 (3)	0.0620 (12)
H17	0.9479	0.5473	0.2026	0.074*
C18	0.7464 (8)	0.58378 (13)	0.3040 (3)	0.0539 (11)
C19	0.6071 (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

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N1	0.047 (2)	0.064 (2)	0.062 (2)	−0.0022 (18)	0.0040 (19)	0.0079 (17)
N2	0.049 (2)	0.057 (2)	0.067 (2)	−0.0032 (18)	0.0078 (18)	0.0001 (17)
N3	0.044 (2)	0.055 (2)	0.076 (2)	0.0024 (17)	0.0234 (18)	−0.0031 (17)
N4	0.040 (2)	0.058 (2)	0.071 (2)	−0.0015 (17)	0.0138 (18)	0.0028 (18)
N5	0.064 (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)
N6	0.063 (3)	0.073 (3)	0.063 (3)	0.014 (2)	0.020 (2)	−0.001 (2)
N7	0.102 (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)
O1	0.073 (2)	0.068 (2)	0.123 (3)	−0.0030 (17)	0.052 (2)	−0.0156 (18)
O2	0.067 (4)	0.067 (3)	0.112 (4)	0.025 (3)	0.009 (3)	0.003 (3)
O3	0.078 (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)
O4	0.066 (2)	0.088 (2)	0.099 (2)	−0.0012 (18)	0.0371 (19)	0.0119 (18)
O5	0.112 (3)	0.088 (3)	0.120 (3)	0.001 (2)	0.060 (2)	−0.023 (2)
C1	0.041 (3)	0.054 (2)	0.052 (3)	0.004 (2)	0.011 (2)	0.001 (2)
C2	0.036 (3)	0.053 (3)	0.062 (3)	−0.004 (2)	0.007 (2)	0.007 (2)
C3	0.046 (3)	0.059 (3)	0.066 (3)	0.004 (2)	0.009 (2)	0.003 (2)
C4	0.037 (3)	0.060 (3)	0.061 (3)	−0.001 (2)	0.006 (2)	0.003 (2)
C5	0.051 (3)	0.062 (3)	0.067 (3)	−0.010 (2)	0.014 (2)	0.002 (2)
C6	0.054 (3)	0.058 (3)	0.064 (3)	−0.003 (2)	0.008 (2)	0.001 (2)
C7	0.054 (3)	0.064 (3)	0.085 (3)	−0.005 (3)	0.019 (3)	−0.006 (2)
C8	0.069 (3)	0.067 (3)	0.109 (4)	−0.012 (3)	0.037 (3)	−0.004 (2)
C9	0.053 (3)	0.074 (3)	0.088 (3)	−0.008 (2)	0.027 (3)	0.001 (3)
C10	0.122 (5)	0.080 (4)	0.097 (4)	−0.006 (3)	0.015 (3)	0.019 (3)
C11	0.045 (3)	0.061 (3)	0.080 (3)	0.005 (2)	0.025 (2)	−0.002 (2)
C12	0.060 (3)	0.084 (3)	0.086 (3)	0.004 (3)	0.005 (3)	−0.016 (2)
C13	0.045 (3)	0.057 (3)	0.048 (3)	0.004 (2)	0.004 (2)	−0.005 (2)
C14	0.043 (3)	0.057 (3)	0.057 (3)	0.003 (2)	0.007 (2)	−0.004 (2)
C15	0.048 (3)	0.068 (3)	0.060 (3)	−0.001 (2)	0.008 (2)	0.004 (2)
C16	0.052 (3)	0.058 (3)	0.057 (3)	0.001 (2)	0.012 (2)	0.000 (2)
C17	0.056 (3)	0.065 (3)	0.066 (3)	0.003 (2)	0.011 (2)	−0.004 (2)
C18	0.046 (3)	0.059 (3)	0.057 (3)	−0.005 (2)	0.006 (2)	0.007 (2)
C19	0.059 (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—N2	1.303 (4)	C7—C8	1.506 (5)
N1—C1	1.379 (4)	C8—H8A	0.9600
N2—C13	1.407 (4)	C8—H8B	0.9600
N3—C7	1.367 (5)	C8—H8C	0.9600
N3—C2	1.382 (4)	C9—C10	1.481 (6)
N3—H3	0.8600	C9—H9A	0.9700
N4—C4	1.347 (4)	C9—H9B	0.9700
N4—C11	1.465 (4)	C10—H10A	0.9600
N4—C9	1.477 (5)	C10—H10B	0.9600
N5—O3	1.211 (12)	C10—H10C	0.9600
N5—O2	1.262 (7)	C11—C12	1.510 (5)
N5—C14	1.460 (6)	C11—H11A	0.9700
N6—O5	1.218 (4)	C11—H11B	0.9700
N6—O4	1.224 (4)	C12—H12A	0.9600
N6—C16	1.464 (5)	C12—H12B	0.9600
N7—C19	1.099 (8)	C12—H12C	0.9600
O1—C7	1.215 (4)	C13—C18	1.396 (5)
C1—C6	1.409 (5)	C13—C14	1.405 (5)
C1—C2	1.426 (5)	C14—C15	1.364 (5)
C2—C3	1.388 (5)	C15—C16	1.366 (5)
C3—C4	1.412 (5)	C15—H15	0.9300
C3—H3A	0.9300	C16—C17	1.373 (5)
C4—C5	1.429 (5)	C17—C18	1.403 (5)
C5—C6	1.349 (5)	C17—H17	0.9300
C5—H5	0.9300	C18—C19	1.465 (6)
C6—H6	0.9300

N2—N1—C1	118.1 (3)	N4—C9—H9A	108.6
N1—N2—C13	110.4 (3)	C10—C9—H9A	108.6
C7—N3—C2	128.8 (3)	N4—C9—H9B	108.6
C7—N3—H3	115.6	C10—C9—H9B	108.6
C2—N3—H3	115.6	H9A—C9—H9B	107.6
C4—N4—C11	121.1 (3)	C9—C10—H10A	109.5
C4—N4—C9	121.4 (3)	C9—C10—H10B	109.5
C11—N4—C9	116.8 (3)	H10A—C10—H10B	109.5
O3—N5—O2	120.2 (8)	C9—C10—H10C	109.5
O3—N5—C14	120.2 (7)	H10A—C10—H10C	109.5
O2—N5—C14	119.5 (5)	H10B—C10—H10C	109.5
O5—N6—O4	123.9 (4)	N4—C11—C12	113.6 (3)
O5—N6—C16	118.3 (4)	N4—C11—H11A	108.8
O4—N6—C16	117.8 (4)	C12—C11—H11A	108.8
N1—C1—C6	113.0 (3)	N4—C11—H11B	108.8
N1—C1—C2	129.1 (3)	C12—C11—H11B	108.8
C6—C1—C2	117.9 (4)	H11A—C11—H11B	107.7
N3—C2—C3	122.1 (3)	C11—C12—H12A	109.5
N3—C2—C1	118.8 (3)	C11—C12—H12B	109.5
C3—C2—C1	119.1 (3)	H12A—C12—H12B	109.5
C2—C3—C4	121.8 (4)	C11—C12—H12C	109.5
C2—C3—H3A	119.1	H12A—C12—H12C	109.5
C4—C3—H3A	119.1	H12B—C12—H12C	109.5
N4—C4—C3	120.4 (4)	C18—C13—C14	116.4 (4)
N4—C4—C5	121.3 (4)	C18—C13—N2	128.1 (4)
C3—C4—C5	118.3 (4)	C14—C13—N2	115.5 (3)
C6—C5—C4	119.4 (4)	C15—C14—C13	123.1 (4)
C6—C5—H5	120.3	C15—C14—N5	118.1 (4)
C4—C5—H5	120.3	C13—C14—N5	118.8 (4)
C5—C6—C1	123.4 (4)	C14—C15—C16	119.0 (4)
C5—C6—H6	118.3	C14—C15—H15	120.5
C1—C6—H6	118.3	C16—C15—H15	120.5
O1—C7—N3	125.0 (4)	C15—C16—C17	121.1 (4)
O1—C7—C8	121.1 (4)	C15—C16—N6	120.3 (4)
N3—C7—C8	113.8 (4)	C17—C16—N6	118.5 (4)
C7—C8—H8A	109.5	C16—C17—C18	119.6 (4)
C7—C8—H8B	109.5	C16—C17—H17	120.2
H8A—C8—H8B	109.5	C18—C17—H17	120.2
C7—C8—H8C	109.5	C13—C18—C17	120.7 (4)
H8A—C8—H8C	109.5	C13—C18—C19	124.7 (4)
H8B—C8—H8C	109.5	C17—C18—C19	114.6 (4)
N4—C9—C10	114.7 (4)	N7—C19—C18	172.6 (7)

C1—N1—N2—C13	178.1 (3)	C9—N4—C11—C12	94.0 (4)
N2—N1—C1—C6	179.7 (3)	N1—N2—C13—C18	−5.6 (5)
N2—N1—C1—C2	0.4 (6)	N1—N2—C13—C14	175.2 (3)
C7—N3—C2—C3	−11.5 (6)	C18—C13—C14—C15	−2.0 (6)
C7—N3—C2—C1	168.6 (4)	N2—C13—C14—C15	177.4 (4)
N1—C1—C2—N3	−0.5 (6)	C18—C13—C14—N5	175.3 (4)
C6—C1—C2—N3	−179.7 (4)	N2—C13—C14—N5	−5.4 (6)
N1—C1—C2—C3	179.6 (4)	O3—N5—C14—C15	−70.7 (8)
C6—C1—C2—C3	0.4 (5)	O2—N5—C14—C15	105.7 (5)
N3—C2—C3—C4	−178.8 (3)	O3—N5—C14—C13	111.9 (7)
C1—C2—C3—C4	1.1 (6)	O2—N5—C14—C13	−71.7 (6)
C11—N4—C4—C3	−5.6 (6)	C13—C14—C15—C16	1.7 (6)
C9—N4—C4—C3	−176.6 (4)	N5—C14—C15—C16	−175.6 (4)
C11—N4—C4—C5	175.4 (4)	C14—C15—C16—C17	−1.0 (6)
C9—N4—C4—C5	4.4 (6)	C14—C15—C16—N6	−178.8 (4)
C2—C3—C4—N4	178.4 (4)	O5—N6—C16—C15	−171.5 (4)
C2—C3—C4—C5	−2.6 (6)	O4—N6—C16—C15	5.6 (6)
N4—C4—C5—C6	−178.4 (4)	O5—N6—C16—C17	10.6 (6)
C3—C4—C5—C6	2.6 (6)	O4—N6—C16—C17	−172.3 (4)
C4—C5—C6—C1	−1.2 (6)	C15—C16—C17—C18	0.6 (6)
N1—C1—C6—C5	−179.6 (4)	N6—C16—C17—C18	178.5 (4)
C2—C1—C6—C5	−0.3 (6)	C14—C13—C18—C17	1.6 (6)
C2—N3—C7—O1	1.6 (7)	N2—C13—C18—C17	−177.7 (4)
C2—N3—C7—C8	−175.1 (4)	C14—C13—C18—C19	179.5 (4)
C4—N4—C9—C10	82.3 (5)	N2—C13—C18—C19	0.3 (7)
C11—N4—C9—C10	−89.0 (5)	C16—C17—C18—C13	−1.0 (6)
C4—N4—C11—C12	−77.3 (5)	C16—C17—C18—C19	−179.1 (4)

Hydrogen-bond geometry (Å, º) top

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

Experimental details

Crystal data
Chemical formula	C₁₉H₁₉N₇O₅
M_r	425.41
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	298
a, b, c (Å)	5.0995 (5), 30.792 (3), 12.7211 (11)
β (°)	93.569 (1)
V (Å³)	1993.6 (3)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.11
Crystal size (mm)	0.37 × 0.11 × 0.07

Data collection
Diffractometer	Bruker SMART CCD area-detector
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.962, 0.993
No. of measured, independent and observed [I > 2σ(I)] reflections	10384, 3487, 1453
R_int	0.108
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.067, 0.157, 1.00
No. of reflections	3487
No. of parameters	311
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	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···A	D—H	H···A	D···A	D—H···A
N3—H3···N2	0.86	2.011	2.676 (4)	133.41

References

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

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Volume 68| Part 10| October 2012| Page o3005

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

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

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Experimental

Crystal data

Data collection

Refinement

Supporting information

References

organic compounds

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