organic compounds
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
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
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Refinement
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Data collection: SMART (Siemens, 1996); cell 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
https://doi.org/10.1107/S160053681203992X/aa2072sup1.cif
contains datablocks I, global. DOI: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
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.
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).
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).
Data collection: SMART (Siemens, 1996); cell
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).Fig. 1. ORTEP drawing of 2-acetylamino-4-(N,N-diethylamino)-2',4'-dinitro-6'-cyanoazobenzene. |
C19H19N7O5 | F(000) = 888 |
Mr = 425.41 | Dx = 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 |
Bruker SMART CCD area-detector diffractometer | 3487 independent reflections |
Radiation source: fine-focus sealed tube | 1453 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.108 |
φ and ω scans | θmax = 25.0°, θmin = 2.6° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −6→6 |
Tmin = 0.962, Tmax = 0.993 | k = −35→36 |
10384 measured reflections | l = −15→12 |
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(Fo2) + (0.0376P)2] where P = (Fo2 + 2Fc2)/3 |
3487 reflections | (Δ/σ)max = 0.001 |
311 parameters | Δρmax = 0.20 e Å−3 |
0 restraints | Δρmin = −0.19 e Å−3 |
C19H19N7O5 | V = 1993.6 (3) Å3 |
Mr = 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)° |
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 = 0.993 | Rint = 0.108 |
10384 measured reflections |
R[F2 > 2σ(F2)] = 0.067 | 0 restraints |
wR(F2) = 0.157 | H-atom parameters constrained |
S = 1.00 | Δρmax = 0.20 e Å−3 |
3487 reflections | Δρmin = −0.19 e Å−3 |
311 parameters |
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. |
x | y | z | Uiso*/Ueq | 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) |
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) |
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) |
Experimental details
Crystal data | |
Chemical formula | C19H19N7O5 |
Mr | 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) |
Tmin, Tmax | 0.962, 0.993 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 10384, 3487, 1453 |
Rint | 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 |
Δρmax, Δρmin (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).
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
This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.
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).