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

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 65| Part 10| October 2009| Pages o2416-o2417

6,6′-Di­amino-1,1′,3,3′-tetra­methyl-5,5′-(4-chloro­benzyl­­idene)bis­­[pyrimidine-2,4(1H,3H)-dione]

aDepartment of Chemical Sciences, Tezpur University, Tezpur 784 028, India, and bDepartment of Chemistry, Indian Institute of Technology Guwahati, Guwahati 781039, India
*Correspondence e-mail: ashim@tezu.ernet.in

(Received 24 August 2009; accepted 4 September 2009; online 9 September 2009)

The title compound, C19H21ClN6O4, is a 1:2 adduct of p-chloro­benzaldehyde and uracil. It crystallizes with two mol­ecules in the asymmetric unit. The two uracil units in the same mol­ecule are connected by a pair of strong N—H⋯O hydrogen bonds. The packing is stabilized by N—H⋯O, C—H⋯O and C—H⋯N inter­actions.

Related literature

For the biological activity and medicinal applications of heterocyclic compounds, especially pyrimidine derivatives, see: Zheng et al. (2007[Zheng, M., Deng, Y., Qiu, S., Luo, X., Chen, K., Liu, H. & Jiang, H. (2007). Bioorg. Med. Chem. Lett. 17, 2414-2420.]); Jain et al. (2006[Jain, K. S., Chitre, T. S., Miniyar, P. B., Kathiravan, M. K., Bendre, V. S., Veer, V. S., Shahane, S. R. & Shishoo, C. J. (2006). Curr. Sci. 90, 793-803.]). The title compound was synthesized from 6-amino- 1,3-dimethyl­pyrimidine-2,4(1H, 3H)-dione, which is an important building block, see: Blicke & Godt (1954[Blicke, F. F. & Godt, H. C. (1954). J. Am. Chem. Soc. 76, 2798-2800.]); Das et al. (2008[Das, S., Saikia, B. K., Sridhar, B. & Thakur, A. J. (2008). Acta Cryst. E64, o1662.]).

[Scheme 1]

Experimental

Crystal data
  • C19H21ClN6O4

  • Mr = 432.87

  • Orthorhombic, P 21 21 21

  • a = 11.5365 (3) Å

  • b = 14.5935 (4) Å

  • c = 23.2102 (6) Å

  • V = 3907.62 (18) Å3

  • Z = 8

  • Mo Kα radiation

  • μ = 0.24 mm−1

  • T = 293 K

  • 0.40 × 0.28 × 0.16 mm

Data collection
  • Bruker SMART CCD area-detector diffractometer

  • Absorption correction: none

  • 53787 measured reflections

  • 9742 independent reflections

  • 6901 reflections with I > 2σ(I)

  • Rint = 0.038

Refinement
  • R[F2 > 2σ(F2)] = 0.056

  • wR(F2) = 0.166

  • S = 1.06

  • 9742 reflections

  • 549 parameters

  • H-atom parameters constrained

  • Δρmax = 1.27 e Å−3

  • Δρmin = −0.28 e Å−3

  • Absolute structure: Flack (1983[Flack, H. D. (1983). Acta Cryst. A39, 876-881.]), 4345 Friedel pairs

  • Flack parameter: 0.15 (8)

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
N3—H3A⋯O4 0.86 2.13 2.966 (4) 164
N3—H3B⋯O1i 0.86 2.26 3.059 (3) 154
N6—H6A⋯O6i 0.86 2.29 3.041 (3) 146
N6—H6B⋯O1 0.86 1.93 2.761 (3) 161
N9—H9A⋯O4ii 0.86 2.51 3.243 (4) 144
N9—H9B⋯O8 0.86 1.98 2.799 (3) 159
N12—H12A⋯O6 0.86 2.09 2.924 (3) 163
N12—H12B⋯O8ii 0.86 2.32 3.106 (3) 153
C1—H1⋯O4 0.98 2.22 2.794 (4) 116
C1—H1⋯N3 0.98 2.41 2.887 (4) 109
C12—H12C⋯O1i 0.96 2.45 3.164 (4) 131
C12—H12D⋯O2 0.96 2.27 2.708 (4) 107
C12—H12D⋯O5iii 0.96 2.60 3.322 (4) 133
C13—H13A⋯O2 0.96 2.36 2.713 (4) 101
C18—H18B⋯O4 0.96 2.24 2.673 (6) 106
C19—H19B⋯O3 0.96 2.23 2.650 (5) 105
C20—H20⋯O6 0.98 2.23 2.807 (4) 116
C20—H20⋯N12 0.98 2.41 2.876 (4) 108
C31—H31B⋯O5 0.96 2.27 2.715 (5) 108
C32—H32A⋯O5 0.96 2.33 2.711 (5) 103
C37—H37A⋯O8ii 0.96 2.57 3.208 (4) 124
C37—H37C⋯O7 0.96 2.28 2.707 (4) 106
C38—H38B⋯O8 0.96 2.27 2.699 (4) 106
Symmetry codes: (i) [-x+1, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]; (ii) [-x+2, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]; (iii) [x-{\script{1\over 2}}, -y+{\script{3\over 2}}, -z+1].

Data collection: SMART (Bruker, 2001[Bruker (2001). SAINT and SMART. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2001[Bruker (2001). SAINT and SMART. 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: XP in SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]).

Supporting information


Comment top

Heterocyclic compounds, especially six-membered pyrimidine ring and their derivatives have occupied an important place among organic compounds owing to their various biological signifiances (Zheng et al., 2007). They have been explored for the development of various pharmaceutically important compounds because of their medicinal values (Jain et al., 2006). They also form the basic structural fragment of many alkaloids and pharmacologically active compounds. As part of our ongoing programme on bioactive pyrimidine molecules, we have synthesized a new pyrimidine compound starting from an important building block namely 6-Amino- 1,3-dimethylpyrimidine-2,4(1H, 3H)-dione (Blicke & Godt, 1954; Das et al., 2008). The title compound crystallizes with two molecules in the asymmetric unit. The two uracil moieties in the same molecule are connected by a pair of strong N—H···O hydrogen bonds. The packing is stabilized by N—H···.O, C—H···.O and C—H···.N interactions.

Related literature top

For the biological activity and medicinal applications of heterocyclic compounds, especially pyrimidine derivatives, see: Zheng et al. (2007); Jain et al. (2006). The title compound was synthesized from 6-amino- 1,3-dimethylpyrimidine-2,4(1H, 3H)-dione, which is an important building block, see: Blicke & Godt (1954); Das et al. (2008)

Experimental top

Distilled water was added in excess to 6-Amino-1,3-dimethylpyrimidine-2,4(1H,3H) -dione (2 mmol) in order to dissolve it completely in a stirring condition. Then, p-chlorobenzaldehyde was added until a precipitate appeared. After 1 hr of stirring the product was filtered and purified by column chromatography. The product was recrystallized by using distilled ethanol, yielding suitable crystals for data collection.

Refinement top

All hydrogen atoms were found in difference Fourier maps. They were refined using a riding model with N-H = 0.86 Å, Caromatic-H = 0.93 Å, Cmethyl-H = 0.96 Å, Ctertiary-H = 0.98 Å and with U(H) set to 1.2 Ueq(C,N) or 1.5 Ueq(Cmethyl).

Computing details top

Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT (Bruker, 2001); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: XP in SHELXTL (Sheldrick, 2008); software used to prepare material for publication: PLATON (Spek, 2009).

Figures top
[Figure 1] Fig. 1. An ORTEP view of the title compound with the atom numbering scheme. Displacement ellipsoids are drawn at the 30% probability level and H atoms are shown as small spheres of arbitrary radii.
6,6'-Diamino-1,1',3,3'-tetramethyl-5,5'-(4-chlorobenzylidene)bis[pyrimidine- 2,4(1H,3H)-dione] top
Crystal data top
C19H21ClN6O4Dx = 1.472 Mg m3
Mr = 432.87Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, P212121Cell parameters from 9985 reflections
a = 11.5365 (3) Åθ = 2.2–25.7°
b = 14.5935 (4) ŵ = 0.24 mm1
c = 23.2102 (6) ÅT = 293 K
V = 3907.62 (18) Å3Blocks, colorless
Z = 80.40 × 0.28 × 0.16 mm
F(000) = 1808
Data collection top
Bruker SMART CCD area-detector
diffractometer
6901 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.038
Graphite monochromatorθmax = 28.4°, θmin = 1.7°
ϕ and ω scansh = 1515
53787 measured reflectionsk = 1919
9742 independent reflectionsl = 3030
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.056H-atom parameters constrained
wR(F2) = 0.166 w = 1/[σ2(Fo2) + (0.09P)2 + 0.7964P]
where P = (Fo2 + 2Fc2)/3
S = 1.06(Δ/σ)max < 0.001
9742 reflectionsΔρmax = 1.27 e Å3
549 parametersΔρmin = 0.28 e Å3
0 restraintsAbsolute structure: Flack (1983), 4345 Friedel pairs
Primary atom site location: structure-invariant direct methodsAbsolute structure parameter: 0.15 (8)
Crystal data top
C19H21ClN6O4V = 3907.62 (18) Å3
Mr = 432.87Z = 8
Orthorhombic, P212121Mo Kα radiation
a = 11.5365 (3) ŵ = 0.24 mm1
b = 14.5935 (4) ÅT = 293 K
c = 23.2102 (6) Å0.40 × 0.28 × 0.16 mm
Data collection top
Bruker SMART CCD area-detector
diffractometer
6901 reflections with I > 2σ(I)
53787 measured reflectionsRint = 0.038
9742 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.056H-atom parameters constrained
wR(F2) = 0.166Δρmax = 1.27 e Å3
S = 1.06Δρmin = 0.28 e Å3
9742 reflectionsAbsolute structure: Flack (1983), 4345 Friedel pairs
549 parametersAbsolute structure parameter: 0.15 (8)
0 restraints
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 > 2σ(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
Cl10.87268 (9)0.84719 (7)0.14783 (4)0.0691 (3)
Cl20.62621 (10)0.67886 (8)0.36362 (6)0.0842 (4)
O81.06232 (19)0.88990 (14)0.27567 (9)0.0449 (5)
N100.9975 (2)1.12225 (16)0.18849 (10)0.0409 (6)
C270.9774 (3)1.0599 (2)0.38507 (12)0.0388 (6)
O10.43437 (19)0.63236 (14)0.23040 (9)0.0462 (5)
N111.0865 (2)0.97903 (16)0.19627 (10)0.0384 (5)
N60.3816 (2)0.59997 (17)0.11616 (11)0.0452 (6)
H6A0.32640.63010.10000.054*
H6B0.40960.61840.14850.054*
N20.4159 (2)0.53819 (17)0.30849 (10)0.0392 (6)
C110.4596 (3)0.55679 (19)0.25331 (12)0.0362 (6)
C140.5145 (3)0.4746 (2)0.11458 (12)0.0403 (7)
C361.0386 (2)0.96383 (19)0.25117 (12)0.0351 (6)
C30.6561 (3)0.6419 (2)0.11131 (12)0.0402 (6)
H30.61260.62290.07980.048*
N10.5063 (2)0.39511 (16)0.31134 (10)0.0386 (6)
C100.4440 (3)0.4624 (2)0.34031 (13)0.0396 (6)
O71.0992 (2)1.06161 (18)0.11334 (10)0.0649 (7)
O60.8555 (2)1.19062 (15)0.38902 (10)0.0514 (5)
C90.5423 (2)0.40516 (19)0.25483 (11)0.0338 (6)
C10.5849 (3)0.50156 (19)0.16763 (12)0.0371 (6)
H10.64710.45580.16800.044*
C300.9395 (3)1.1447 (2)0.40763 (13)0.0421 (7)
N91.1133 (2)0.93617 (19)0.38994 (12)0.0477 (6)
H9A1.16930.90940.40760.057*
H9B1.08520.91260.35900.057*
C200.9093 (2)1.02501 (19)0.33366 (12)0.0353 (6)
H200.84551.06910.33100.042*
C340.9553 (3)1.11502 (19)0.24430 (12)0.0355 (6)
O40.6321 (3)0.34234 (19)0.10500 (11)0.0808 (10)
C330.9683 (3)1.03421 (19)0.27454 (12)0.0345 (6)
N30.5937 (2)0.33165 (16)0.23116 (11)0.0435 (6)
H3A0.61950.33430.19640.052*
H3B0.60090.28190.25070.052*
N50.3759 (2)0.49787 (19)0.03907 (11)0.0450 (6)
O20.4133 (3)0.45193 (18)0.38953 (10)0.0665 (7)
C170.4243 (3)0.5239 (2)0.09087 (13)0.0398 (7)
N120.9021 (2)1.18920 (17)0.26519 (11)0.0446 (6)
H12A0.87351.18840.29940.054*
H12B0.89651.23780.24440.054*
C80.5272 (3)0.48760 (19)0.22656 (12)0.0357 (6)
C240.7074 (3)0.7778 (2)0.35625 (15)0.0497 (8)
C210.8455 (2)0.93356 (19)0.34220 (12)0.0347 (6)
N80.9983 (2)1.1785 (2)0.45592 (11)0.0516 (7)
C20.6515 (2)0.59179 (19)0.16235 (12)0.0369 (6)
N71.1188 (2)1.0487 (2)0.46059 (11)0.0511 (7)
C351.0637 (3)1.0546 (2)0.16289 (13)0.0437 (7)
C40.7240 (3)0.7190 (2)0.10674 (14)0.0450 (7)
H40.72530.75190.07240.054*
O51.1412 (2)1.1681 (2)0.52252 (11)0.0755 (8)
C70.7218 (3)0.6211 (2)0.20748 (13)0.0447 (7)
H70.72190.58820.24180.054*
C220.7752 (3)0.9018 (2)0.29750 (13)0.0407 (7)
H220.77490.93290.26250.049*
C260.8422 (3)0.8873 (2)0.39395 (13)0.0405 (7)
H260.88650.90850.42470.049*
C120.5385 (3)0.3124 (2)0.34431 (14)0.0515 (8)
H12C0.49770.26040.32910.077*
H12D0.51810.32070.38410.077*
H12E0.62040.30230.34120.077*
O30.3531 (3)0.3928 (2)0.03150 (11)0.0852 (9)
C230.7055 (3)0.8249 (2)0.30412 (14)0.0471 (7)
H230.65830.80520.27410.057*
C50.7897 (3)0.7477 (2)0.15242 (14)0.0436 (7)
C150.5501 (4)0.3921 (3)0.08698 (13)0.0562 (9)
C60.7909 (3)0.6971 (2)0.20284 (14)0.0488 (8)
H60.83820.71460.23340.059*
C160.4053 (4)0.4160 (3)0.01292 (15)0.0588 (10)
C250.7737 (3)0.8091 (2)0.40128 (15)0.0487 (8)
H250.77310.77850.43640.058*
N40.4919 (3)0.3658 (2)0.03778 (11)0.0617 (9)
C291.0896 (3)1.1343 (3)0.48273 (14)0.0561 (9)
C281.0693 (3)1.0151 (2)0.41075 (13)0.0432 (7)
C370.9705 (4)1.2031 (2)0.15333 (14)0.0581 (9)
H37A1.01691.25390.16590.087*
H37B0.88991.21810.15750.087*
H37C0.98701.19010.11360.087*
C130.3377 (3)0.6053 (2)0.33519 (14)0.0520 (8)
H13A0.29200.57570.36430.078*
H13B0.28750.63070.30630.078*
H13C0.38250.65350.35240.078*
C381.1673 (3)0.9112 (2)0.17263 (15)0.0513 (8)
H38A1.12960.87710.14260.077*
H38B1.19140.87020.20270.077*
H38C1.23390.94200.15710.077*
C190.2869 (3)0.5538 (3)0.00979 (15)0.0596 (9)
H19A0.21400.54680.02920.089*
H19B0.27920.53400.02950.089*
H19C0.30960.61710.01060.089*
C311.2062 (4)0.9963 (3)0.49141 (17)0.0708 (12)
H31A1.17360.93920.50390.106*
H31B1.23201.03050.52430.106*
H31C1.27080.98470.46640.106*
C320.9631 (4)1.2684 (3)0.47975 (17)0.0706 (12)
H32A0.98991.27360.51880.106*
H32B0.88011.27330.47900.106*
H32C0.99631.31660.45690.106*
C180.5258 (6)0.2797 (3)0.01056 (19)0.109 (2)
H18A0.45770.24600.00020.163*
H18B0.57100.24410.03710.163*
H18C0.57120.29240.02320.163*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl10.0614 (6)0.0759 (6)0.0700 (6)0.0308 (5)0.0047 (5)0.0041 (5)
Cl20.0732 (7)0.0615 (6)0.1179 (9)0.0344 (5)0.0091 (6)0.0144 (6)
O80.0568 (14)0.0364 (11)0.0415 (11)0.0065 (10)0.0041 (10)0.0002 (9)
N100.0547 (15)0.0348 (12)0.0331 (12)0.0055 (11)0.0044 (11)0.0006 (10)
C270.0420 (16)0.0391 (15)0.0353 (14)0.0089 (13)0.0064 (13)0.0026 (12)
O10.0599 (14)0.0363 (11)0.0422 (11)0.0113 (10)0.0016 (10)0.0011 (9)
N110.0389 (13)0.0387 (13)0.0374 (13)0.0029 (10)0.0045 (11)0.0033 (10)
N60.0435 (14)0.0437 (14)0.0484 (14)0.0042 (11)0.0080 (12)0.0082 (12)
N20.0410 (13)0.0387 (13)0.0380 (13)0.0004 (11)0.0074 (11)0.0024 (10)
C110.0424 (16)0.0326 (14)0.0334 (14)0.0011 (12)0.0020 (13)0.0027 (11)
C140.0546 (18)0.0343 (14)0.0321 (14)0.0010 (13)0.0075 (13)0.0004 (11)
C360.0352 (15)0.0343 (14)0.0357 (14)0.0028 (12)0.0006 (12)0.0055 (11)
C30.0405 (16)0.0462 (16)0.0340 (14)0.0016 (13)0.0024 (13)0.0045 (13)
N10.0491 (15)0.0311 (12)0.0357 (12)0.0046 (10)0.0015 (11)0.0034 (10)
C100.0431 (16)0.0417 (16)0.0339 (15)0.0028 (13)0.0063 (13)0.0013 (12)
O70.0772 (17)0.0715 (17)0.0459 (13)0.0076 (14)0.0232 (13)0.0079 (12)
O60.0567 (14)0.0451 (12)0.0525 (13)0.0015 (11)0.0085 (11)0.0105 (10)
C90.0357 (15)0.0337 (14)0.0320 (14)0.0027 (11)0.0005 (12)0.0007 (11)
C10.0434 (16)0.0329 (14)0.0349 (14)0.0083 (12)0.0024 (12)0.0035 (11)
C300.0435 (17)0.0425 (16)0.0404 (16)0.0154 (14)0.0115 (13)0.0097 (13)
N90.0459 (15)0.0518 (15)0.0455 (14)0.0006 (12)0.0062 (12)0.0039 (12)
C200.0351 (14)0.0348 (14)0.0360 (14)0.0038 (11)0.0029 (12)0.0021 (11)
C340.0368 (15)0.0326 (14)0.0371 (14)0.0045 (11)0.0003 (12)0.0028 (11)
O40.137 (3)0.0604 (16)0.0452 (13)0.0466 (18)0.0001 (16)0.0088 (12)
C330.0406 (16)0.0334 (14)0.0296 (13)0.0047 (12)0.0039 (12)0.0051 (11)
N30.0613 (16)0.0313 (12)0.0380 (13)0.0064 (12)0.0050 (12)0.0043 (10)
N50.0443 (15)0.0530 (15)0.0377 (13)0.0016 (12)0.0070 (11)0.0035 (12)
O20.094 (2)0.0638 (16)0.0421 (13)0.0103 (14)0.0229 (14)0.0082 (12)
C170.0417 (16)0.0396 (15)0.0381 (15)0.0061 (13)0.0102 (13)0.0025 (12)
N120.0573 (16)0.0337 (12)0.0430 (13)0.0029 (12)0.0063 (12)0.0026 (11)
C80.0404 (16)0.0322 (14)0.0347 (14)0.0013 (12)0.0014 (12)0.0024 (11)
C240.0365 (16)0.0418 (16)0.071 (2)0.0085 (13)0.0025 (16)0.0015 (16)
C210.0331 (14)0.0334 (14)0.0375 (14)0.0017 (11)0.0027 (12)0.0010 (11)
N80.0562 (17)0.0572 (17)0.0415 (14)0.0141 (14)0.0102 (13)0.0173 (13)
C20.0369 (15)0.0382 (15)0.0355 (14)0.0087 (12)0.0068 (12)0.0019 (11)
N70.0448 (15)0.0738 (19)0.0347 (13)0.0116 (14)0.0010 (12)0.0082 (13)
C350.0463 (17)0.0463 (17)0.0386 (16)0.0049 (13)0.0045 (14)0.0058 (13)
C40.0391 (16)0.0514 (18)0.0446 (16)0.0070 (14)0.0058 (14)0.0097 (14)
O50.0670 (17)0.109 (2)0.0505 (14)0.0212 (17)0.0030 (13)0.0290 (15)
C70.0473 (18)0.0517 (18)0.0351 (15)0.0068 (15)0.0039 (13)0.0084 (14)
C220.0403 (16)0.0426 (16)0.0393 (15)0.0019 (13)0.0062 (13)0.0013 (13)
C260.0352 (15)0.0451 (16)0.0411 (15)0.0064 (13)0.0025 (13)0.0019 (13)
C120.077 (2)0.0342 (15)0.0434 (16)0.0047 (15)0.0043 (17)0.0115 (13)
O30.111 (2)0.097 (2)0.0483 (15)0.003 (2)0.0025 (16)0.0330 (15)
C230.0373 (16)0.0462 (18)0.0578 (19)0.0046 (14)0.0075 (14)0.0057 (15)
C50.0323 (15)0.0494 (17)0.0492 (17)0.0044 (13)0.0040 (14)0.0009 (14)
C150.083 (3)0.052 (2)0.0332 (16)0.0119 (19)0.0099 (17)0.0019 (14)
C60.0408 (17)0.058 (2)0.0476 (18)0.0013 (15)0.0088 (14)0.0032 (15)
C160.069 (2)0.069 (2)0.0384 (17)0.009 (2)0.0109 (17)0.0094 (17)
C250.0457 (17)0.0458 (18)0.0546 (19)0.0040 (14)0.0005 (15)0.0139 (15)
N40.099 (3)0.0522 (17)0.0336 (13)0.0071 (17)0.0081 (15)0.0124 (13)
C290.059 (2)0.074 (2)0.0352 (16)0.0236 (19)0.0099 (16)0.0163 (17)
C280.0427 (17)0.0527 (19)0.0341 (15)0.0165 (14)0.0045 (13)0.0025 (13)
C370.089 (3)0.0460 (19)0.0389 (16)0.0015 (18)0.0128 (18)0.0104 (14)
C130.0527 (19)0.0535 (19)0.0497 (18)0.0154 (16)0.0073 (16)0.0052 (15)
C380.0471 (18)0.054 (2)0.0532 (19)0.0068 (15)0.0106 (16)0.0085 (15)
C190.052 (2)0.084 (3)0.0426 (17)0.0011 (19)0.0005 (16)0.0002 (18)
C310.064 (3)0.093 (3)0.055 (2)0.001 (2)0.0132 (19)0.010 (2)
C320.084 (3)0.065 (2)0.063 (2)0.016 (2)0.021 (2)0.035 (2)
C180.193 (6)0.074 (3)0.059 (3)0.043 (4)0.000 (3)0.032 (2)
Geometric parameters (Å, º) top
Cl1—C51.743 (3)N12—H12A0.8600
Cl2—C241.730 (3)N12—H12B0.8600
O8—C361.250 (3)C24—C251.373 (5)
N10—C351.383 (4)C24—C231.392 (5)
N10—C341.388 (4)C21—C261.379 (4)
N10—C371.468 (4)C21—C221.396 (4)
C27—C281.381 (5)N8—C291.383 (5)
C27—C301.414 (4)N8—C321.481 (4)
C27—C201.517 (4)C2—C71.392 (4)
O1—C111.258 (3)N7—C281.380 (4)
N11—C351.373 (4)N7—C291.393 (5)
N11—C361.406 (4)N7—C311.454 (5)
N11—C381.466 (4)C4—C51.369 (4)
N6—C171.349 (4)C4—H40.9300
N6—H6A0.8600O5—C291.204 (4)
N6—H6B0.8600C7—C61.369 (5)
N2—C101.369 (4)C7—H70.9300
N2—C111.403 (4)C22—C231.388 (4)
N2—C131.469 (4)C22—H220.9300
C11—C81.419 (4)C26—C251.397 (4)
C14—C171.380 (4)C26—H260.9300
C14—C151.424 (4)C12—H12C0.9600
C14—C11.527 (4)C12—H12D0.9600
C36—C331.417 (4)C12—H12E0.9600
C3—C41.376 (4)O3—C161.241 (4)
C3—C21.393 (4)C23—H230.9300
C3—H30.9300C5—C61.383 (4)
N1—C91.384 (4)C15—N41.379 (5)
N1—C101.391 (4)C6—H60.9300
N1—C121.477 (4)C16—N41.367 (5)
C10—O21.206 (4)C25—H250.9300
O7—C351.225 (4)N4—C181.460 (5)
O6—C301.254 (4)C37—H37A0.9600
C9—N31.343 (4)C37—H37B0.9600
C9—C81.381 (4)C37—H37C0.9600
C1—C21.530 (4)C13—H13A0.9600
C1—C81.535 (4)C13—H13B0.9600
C1—H10.9800C13—H13C0.9600
C30—N81.400 (4)C38—H38A0.9600
N9—C281.347 (4)C38—H38B0.9600
N9—H9A0.8600C38—H38C0.9600
N9—H9B0.8600C19—H19A0.9600
C20—C211.537 (4)C19—H19B0.9600
C20—C331.538 (4)C19—H19C0.9600
C20—H200.9800C31—H31A0.9600
C34—N121.335 (4)C31—H31B0.9600
C34—C331.380 (4)C31—H31C0.9600
O4—C151.264 (5)C32—H32A0.9600
N3—H3A0.8600C32—H32B0.9600
N3—H3B0.8600C32—H32C0.9600
N5—C171.379 (4)C18—H18A0.9600
N5—C161.382 (5)C18—H18B0.9600
N5—C191.478 (5)C18—H18C0.9600
C35—N10—C34122.7 (2)O7—C35—N11122.2 (3)
C35—N10—C37116.9 (2)O7—C35—N10121.9 (3)
C34—N10—C37120.4 (3)N11—C35—N10115.9 (2)
C28—C27—C30119.5 (3)C5—C4—C3120.4 (3)
C28—C27—C20125.3 (3)C5—C4—H4119.8
C30—C27—C20115.1 (3)C3—C4—H4119.8
C35—N11—C36124.2 (2)C6—C7—C2121.9 (3)
C35—N11—C38116.9 (3)C6—C7—H7119.0
C36—N11—C38118.8 (3)C2—C7—H7119.0
C17—N6—H6A120.0C23—C22—C21121.5 (3)
C17—N6—H6B120.0C23—C22—H22119.3
H6A—N6—H6B120.0C21—C22—H22119.3
C10—N2—C11124.4 (2)C21—C26—C25121.4 (3)
C10—N2—C13117.2 (2)C21—C26—H26119.3
C11—N2—C13118.5 (2)C25—C26—H26119.3
O1—C11—N2118.2 (3)N1—C12—H12C109.5
O1—C11—C8124.5 (3)N1—C12—H12D109.5
N2—C11—C8117.3 (2)H12C—C12—H12D109.5
C17—C14—C15118.6 (3)N1—C12—H12E109.5
C17—C14—C1126.1 (3)H12C—C12—H12E109.5
C15—C14—C1115.3 (3)H12D—C12—H12E109.5
O8—C36—N11117.5 (3)C22—C23—C24119.1 (3)
O8—C36—C33125.2 (3)C22—C23—H23120.5
N11—C36—C33117.2 (3)C24—C23—H23120.5
C4—C3—C2121.1 (3)C4—C5—C6119.9 (3)
C4—C3—H3119.4C4—C5—Cl1120.8 (2)
C2—C3—H3119.4C6—C5—Cl1119.4 (2)
C9—N1—C10122.6 (2)O4—C15—N4118.6 (3)
C9—N1—C12120.2 (3)O4—C15—C14123.6 (3)
C10—N1—C12117.2 (2)N4—C15—C14117.9 (3)
O2—C10—N2123.0 (3)C7—C6—C5119.5 (3)
O2—C10—N1121.4 (3)C7—C6—H6120.2
N2—C10—N1115.6 (2)C5—C6—H6120.2
N3—C9—C8123.8 (3)O3—C16—N4124.0 (4)
N3—C9—N1115.8 (2)O3—C16—N5118.8 (4)
C8—C9—N1120.3 (3)N4—C16—N5117.2 (3)
C14—C1—C2115.1 (2)C24—C25—C26119.6 (3)
C14—C1—C8117.0 (2)C24—C25—H25120.2
C2—C1—C8113.8 (2)C26—C25—H25120.2
C14—C1—H1102.7C16—N4—C15123.8 (3)
C2—C1—H1102.7C16—N4—C18118.4 (4)
C8—C1—H1102.7C15—N4—C18117.9 (4)
O6—C30—N8117.5 (3)O5—C29—N8122.1 (4)
O6—C30—C27125.4 (3)O5—C29—N7122.1 (4)
N8—C30—C27117.0 (3)N8—C29—N7115.9 (3)
C28—N9—H9A120.0N9—C28—N7116.7 (3)
C28—N9—H9B120.0N9—C28—C27122.6 (3)
H9A—N9—H9B120.0N7—C28—C27120.7 (3)
C27—C20—C21116.0 (2)N10—C37—H37A109.5
C27—C20—C33116.3 (2)N10—C37—H37B109.5
C21—C20—C33113.8 (2)H37A—C37—H37B109.5
C27—C20—H20102.6N10—C37—H37C109.5
C21—C20—H20102.6H37A—C37—H37C109.5
C33—C20—H20102.6H37B—C37—H37C109.5
N12—C34—C33123.9 (3)N2—C13—H13A109.5
N12—C34—N10116.0 (2)N2—C13—H13B109.5
C33—C34—N10120.1 (3)H13A—C13—H13B109.5
C34—C33—C36119.1 (3)N2—C13—H13C109.5
C34—C33—C20118.7 (3)H13A—C13—H13C109.5
C36—C33—C20122.1 (3)H13B—C13—H13C109.5
C9—N3—H3A120.0N11—C38—H38A109.5
C9—N3—H3B120.0N11—C38—H38B109.5
H3A—N3—H3B120.0H38A—C38—H38B109.5
C17—N5—C16121.5 (3)N11—C38—H38C109.5
C17—N5—C19122.0 (3)H38A—C38—H38C109.5
C16—N5—C19116.5 (3)H38B—C38—H38C109.5
N6—C17—N5117.3 (3)N5—C19—H19A109.5
N6—C17—C14122.1 (3)N5—C19—H19B109.5
N5—C17—C14120.6 (3)H19A—C19—H19B109.5
C34—N12—H12A120.0N5—C19—H19C109.5
C34—N12—H12B120.0H19A—C19—H19C109.5
H12A—N12—H12B120.0H19B—C19—H19C109.5
C9—C8—C11118.8 (3)N7—C31—H31A109.5
C9—C8—C1119.0 (3)N7—C31—H31B109.5
C11—C8—C1122.3 (2)H31A—C31—H31B109.5
C25—C24—C23120.4 (3)N7—C31—H31C109.5
C25—C24—Cl2120.3 (3)H31A—C31—H31C109.5
C23—C24—Cl2119.3 (3)H31B—C31—H31C109.5
C26—C21—C22117.9 (3)N8—C32—H32A109.5
C26—C21—C20123.4 (3)N8—C32—H32B109.5
C22—C21—C20118.1 (3)H32A—C32—H32B109.5
C29—N8—C30124.4 (3)N8—C32—H32C109.5
C29—N8—C32117.0 (3)H32A—C32—H32C109.5
C30—N8—C32118.5 (3)H32B—C32—H32C109.5
C7—C2—C3117.1 (3)N4—C18—H18A109.5
C7—C2—C1119.8 (3)N4—C18—H18B109.5
C3—C2—C1122.6 (3)H18A—C18—H18B109.5
C28—N7—C29121.9 (3)N4—C18—H18C109.5
C28—N7—C31120.8 (3)H18A—C18—H18C109.5
C29—N7—C31117.2 (3)H18B—C18—H18C109.5
C10—N2—C11—O1174.5 (3)C27—C20—C21—C22175.6 (3)
C13—N2—C11—O13.5 (4)C33—C20—C21—C2245.5 (4)
C10—N2—C11—C87.0 (4)O6—C30—N8—C29177.5 (3)
C13—N2—C11—C8175.0 (3)C27—C30—N8—C290.4 (4)
C35—N11—C36—O8176.5 (3)O6—C30—N8—C323.7 (4)
C38—N11—C36—O84.3 (4)C27—C30—N8—C32178.3 (3)
C35—N11—C36—C334.1 (4)C4—C3—C2—C72.5 (4)
C38—N11—C36—C33175.0 (3)C4—C3—C2—C1174.9 (3)
C11—N2—C10—O2173.3 (3)C14—C1—C2—C7177.7 (3)
C13—N2—C10—O24.7 (5)C8—C1—C2—C743.3 (4)
C11—N2—C10—N19.5 (4)C14—C1—C2—C35.4 (4)
C13—N2—C10—N1172.4 (3)C8—C1—C2—C3144.4 (3)
C9—N1—C10—O2179.8 (3)C36—N11—C35—O7173.6 (3)
C12—N1—C10—O23.0 (5)C38—N11—C35—O77.2 (5)
C9—N1—C10—N22.6 (4)C36—N11—C35—N106.0 (4)
C12—N1—C10—N2179.8 (3)C38—N11—C35—N10173.2 (3)
C10—N1—C9—N3175.0 (3)C34—N10—C35—O7179.2 (3)
C12—N1—C9—N37.9 (4)C37—N10—C35—O70.5 (5)
C10—N1—C9—C86.6 (4)C34—N10—C35—N110.5 (4)
C12—N1—C9—C8170.5 (3)C37—N10—C35—N11179.1 (3)
C17—C14—C1—C261.2 (4)C2—C3—C4—C50.7 (5)
C15—C14—C1—C2116.5 (3)C3—C2—C7—C61.5 (4)
C17—C14—C1—C876.4 (4)C1—C2—C7—C6174.2 (3)
C15—C14—C1—C8105.8 (3)C26—C21—C22—C231.3 (4)
C28—C27—C30—O6178.1 (3)C20—C21—C22—C23173.2 (3)
C20—C27—C30—O60.8 (4)C22—C21—C26—C252.1 (4)
C28—C27—C30—N80.3 (4)C20—C21—C26—C25173.5 (3)
C20—C27—C30—N8178.6 (2)C21—C22—C23—C241.0 (5)
C28—C27—C20—C2161.2 (4)C25—C24—C23—C222.6 (5)
C30—C27—C20—C21117.7 (3)Cl2—C24—C23—C22176.9 (2)
C28—C27—C20—C3376.6 (4)C3—C4—C5—C62.2 (5)
C30—C27—C20—C33104.5 (3)C3—C4—C5—Cl1178.1 (2)
C35—N10—C34—N12173.9 (3)C17—C14—C15—O4179.5 (3)
C37—N10—C34—N127.6 (4)C1—C14—C15—O41.6 (5)
C35—N10—C34—C336.8 (4)C17—C14—C15—N40.1 (5)
C37—N10—C34—C33171.7 (3)C1—C14—C15—N4178.1 (3)
N12—C34—C33—C36172.1 (3)C2—C7—C6—C51.3 (5)
N10—C34—C33—C368.6 (4)C4—C5—C6—C73.1 (5)
N12—C34—C33—C205.7 (4)Cl1—C5—C6—C7177.1 (2)
N10—C34—C33—C20173.5 (2)C17—N5—C16—O3174.9 (3)
O8—C36—C33—C34175.9 (3)C19—N5—C16—O32.8 (5)
N11—C36—C33—C343.4 (4)C17—N5—C16—N45.8 (5)
O8—C36—C33—C201.9 (4)C19—N5—C16—N4176.6 (3)
N11—C36—C33—C20178.8 (2)C23—C24—C25—C261.9 (5)
C27—C20—C33—C3486.8 (3)Cl2—C24—C25—C26177.6 (2)
C21—C20—C33—C34134.4 (3)C21—C26—C25—C240.5 (5)
C27—C20—C33—C3690.9 (3)O3—C16—N4—C15179.6 (4)
C21—C20—C33—C3647.8 (4)N5—C16—N4—C150.3 (5)
C16—N5—C17—N6173.1 (3)O3—C16—N4—C180.2 (6)
C19—N5—C17—N64.4 (4)N5—C16—N4—C18179.1 (4)
C16—N5—C17—C148.3 (4)O4—C15—N4—C16177.1 (4)
C19—N5—C17—C14174.1 (3)C14—C15—N4—C162.6 (5)
C15—C14—C17—N6176.4 (3)O4—C15—N4—C182.3 (6)
C1—C14—C17—N65.9 (5)C14—C15—N4—C18178.0 (4)
C15—C14—C17—N55.2 (4)C30—N8—C29—O5176.4 (3)
C1—C14—C17—N5172.5 (3)C32—N8—C29—O52.4 (5)
N3—C9—C8—C11172.6 (3)C30—N8—C29—N73.1 (4)
N1—C9—C8—C119.1 (4)C32—N8—C29—N7178.1 (3)
N3—C9—C8—C17.9 (5)C28—N7—C29—O5171.8 (3)
N1—C9—C8—C1170.4 (3)C31—N7—C29—O56.6 (5)
O1—C11—C8—C9175.7 (3)C28—N7—C29—N87.7 (4)
N2—C11—C8—C92.7 (4)C31—N7—C29—N8173.8 (3)
O1—C11—C8—C14.7 (5)C29—N7—C28—N9172.9 (3)
N2—C11—C8—C1176.8 (3)C31—N7—C28—N95.6 (4)
C14—C1—C8—C990.4 (3)C29—N7—C28—C278.8 (4)
C2—C1—C8—C9131.4 (3)C31—N7—C28—C27172.8 (3)
C14—C1—C8—C1190.1 (3)C30—C27—C28—N9176.9 (3)
C2—C1—C8—C1148.1 (4)C20—C27—C28—N94.2 (5)
C27—C20—C21—C264.2 (4)C30—C27—C28—N74.8 (4)
C33—C20—C21—C26143.1 (3)C20—C27—C28—N7174.0 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N3—H3A···O40.862.132.966 (4)164
N3—H3B···O1i0.862.263.059 (3)154
N6—H6A···O6i0.862.293.041 (3)146
N6—H6B···O10.861.932.761 (3)161
N9—H9A···O4ii0.862.513.243 (4)144
N9—H9B···O80.861.982.799 (3)159
N12—H12A···O60.862.092.924 (3)163
N12—H12B···O8ii0.862.323.106 (3)153
C1—H1···O40.982.222.794 (4)116
C1—H1···N30.982.412.887 (4)109
C12—H12C···O1i0.962.453.164 (4)131
C12—H12D···O20.962.272.708 (4)107
C12—H12D···O5iii0.962.603.322 (4)133
C13—H13A···O20.962.362.713 (4)101
C18—H18B···O40.962.242.673 (6)106
C19—H19B···O30.962.232.650 (5)105
C20—H20···O60.982.232.807 (4)116
C20—H20···N120.982.412.876 (4)108
C31—H31B···O50.962.272.715 (5)108
C32—H32A···O50.962.332.711 (5)103
C37—H37A···O8ii0.962.573.208 (4)124
C37—H37C···O70.962.282.707 (4)106
C38—H38B···O80.962.272.699 (4)106
Symmetry codes: (i) x+1, y1/2, z+1/2; (ii) x+2, y+1/2, z+1/2; (iii) x1/2, y+3/2, z+1.

Experimental details

Crystal data
Chemical formulaC19H21ClN6O4
Mr432.87
Crystal system, space groupOrthorhombic, P212121
Temperature (K)293
a, b, c (Å)11.5365 (3), 14.5935 (4), 23.2102 (6)
V3)3907.62 (18)
Z8
Radiation typeMo Kα
µ (mm1)0.24
Crystal size (mm)0.40 × 0.28 × 0.16
Data collection
DiffractometerBruker SMART CCD area-detector
diffractometer
Absorption correction
No. of measured, independent and
observed [I > 2σ(I)] reflections
53787, 9742, 6901
Rint0.038
(sin θ/λ)max1)0.669
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.056, 0.166, 1.06
No. of reflections9742
No. of parameters549
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)1.27, 0.28
Absolute structureFlack (1983), 4345 Friedel pairs
Absolute structure parameter0.15 (8)

Computer programs: SMART (Bruker, 2001), SAINT (Bruker, 2001), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), XP in SHELXTL (Sheldrick, 2008), PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N3—H3A···O40.86002.13002.966 (4)164.00
N3—H3B···O1i0.86002.26003.059 (3)154.00
N6—H6A···O6i0.86002.29003.041 (3)146.00
N6—H6B···O10.86001.93002.761 (3)161.00
N9—H9A···O4ii0.86002.51003.243 (4)144.00
N9—H9B···O80.86001.98002.799 (3)159.00
N12—H12A···O60.86002.09002.924 (3)163.00
N12—H12B···O8ii0.86002.32003.106 (3)153.00
C1—H1···O40.98002.22002.794 (4)116.00
C1—H1···N30.98002.41002.887 (4)109.00
C12—H12C···O1i0.96002.45003.164 (4)131.00
C12—H12D···O20.96002.27002.708 (4)107.00
C12—H12D···O5iii0.96002.60003.322 (4)133.00
C13—H13A···O20.96002.36002.713 (4)101.00
C18—H18B···O40.96002.24002.673 (6)106.00
C19—H19B···O30.96002.23002.650 (5)105.00
C20—H20···O60.98002.23002.807 (4)116.00
C20—H20···N120.98002.41002.876 (4)108.00
C31—H31B···O50.96002.27002.715 (5)108.00
C32—H32A···O50.96002.33002.711 (5)103.00
C37—H37A···O8ii0.96002.57003.208 (4)124.00
C37—H37C···O70.96002.28002.707 (4)106.00
C38—H38B···O80.96002.27002.699 (4)106.00
Symmetry codes: (i) x+1, y1/2, z+1/2; (ii) x+2, y+1/2, z+1/2; (iii) x1/2, y+3/2, z+1.
 

Acknowledgements

AJT thanks the Council of Scientific and Industrial Research (CSIR), New Delhi, India, for financial support. The authors are grateful to Mr Sanchay Jyoti Bora, Pandu College, Guwahati, India for his suggestions.

References

First citationBlicke, F. F. & Godt, H. C. (1954). J. Am. Chem. Soc. 76, 2798–2800.  CrossRef CAS Web of Science Google Scholar
First citationBruker (2001). SAINT and SMART. Bruker AXS Inc., Madison, Wisconsin, USA.  Google Scholar
First citationDas, S., Saikia, B. K., Sridhar, B. & Thakur, A. J. (2008). Acta Cryst. E64, o1662.  Web of Science CSD CrossRef IUCr Journals Google Scholar
First citationFlack, H. D. (1983). Acta Cryst. A39, 876–881.  CrossRef CAS Web of Science IUCr Journals Google Scholar
First citationJain, K. S., Chitre, T. S., Miniyar, P. B., Kathiravan, M. K., Bendre, V. S., Veer, V. S., Shahane, S. R. & Shishoo, C. J. (2006). Curr. Sci. 90, 793–803.  CAS 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 citationZheng, M., Deng, Y., Qiu, S., Luo, X., Chen, K., Liu, H. & Jiang, H. (2007). Bioorg. Med. Chem. Lett. 17, 2414–2420.  Web of Science CrossRef PubMed CAS 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.

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 65| Part 10| October 2009| Pages o2416-o2417
Follow Acta Cryst. E
Sign up for e-alerts
Follow Acta Cryst. on Twitter
Follow us on facebook
Sign up for RSS feeds