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Acta Crystallogr Sect E Struct Rep Online. 2009 October 1; 65(Pt 10): o2416–o2417.
Published online 2009 September 9. doi:  10.1107/S1600536809035818
PMCID: PMC2970351

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

Abstract

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 [triangle]); Jain et al. (2006 [triangle]). 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 [triangle]); Das et al. (2008 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-65-o2416-scheme1.jpg

Experimental

Crystal data

  • C19H21ClN6O4
  • M r = 432.87
  • Orthorhombic, An external file that holds a picture, illustration, etc.
Object name is e-65-o2416-efi1.jpg
  • 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)
  • R int = 0.038

Refinement

  • R[F 2 > 2σ(F 2)] = 0.056
  • wR(F 2) = 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 [triangle]), 4345 Friedel pairs
  • Flack parameter: 0.15 (8)

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

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809035818/bt5045sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809035818/bt5045Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Acknowledgments

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.

supplementary crystallographic information

Comment

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.

Experimental

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

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).

Figures

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.

Crystal data

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

Bruker SMART CCD area-detector diffractometer6901 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.038
graphiteθmax = 28.4°, θmin = 1.7°
[var phi] and ω scansh = −15→15
53787 measured reflectionsk = −19→19
9742 independent reflectionsl = −30→30

Refinement

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) = 0.166w = 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 methodsFlack parameter: 0.15 (8)

Special details

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)

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*
H19B0.27920.5340−0.02950.089*
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)
H18A0.45770.2460−0.00020.163*
H18B0.57100.24410.03710.163*
H18C0.57120.2924−0.02320.163*

Atomic displacement parameters (Å2)

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, °)

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—O1−174.5 (3)C27—C20—C21—C22175.6 (3)
C13—N2—C11—O13.5 (4)C33—C20—C21—C22−45.5 (4)
C10—N2—C11—C87.0 (4)O6—C30—N8—C29177.5 (3)
C13—N2—C11—C8−175.0 (3)C27—C30—N8—C29−0.4 (4)
C35—N11—C36—O8176.5 (3)O6—C30—N8—C32−3.7 (4)
C38—N11—C36—O8−4.3 (4)C27—C30—N8—C32178.3 (3)
C35—N11—C36—C33−4.1 (4)C4—C3—C2—C7−2.5 (4)
C38—N11—C36—C33175.0 (3)C4—C3—C2—C1−174.9 (3)
C11—N2—C10—O2173.3 (3)C14—C1—C2—C7−177.7 (3)
C13—N2—C10—O2−4.7 (5)C8—C1—C2—C743.3 (4)
C11—N2—C10—N1−9.5 (4)C14—C1—C2—C3−5.4 (4)
C13—N2—C10—N1172.4 (3)C8—C1—C2—C3−144.4 (3)
C9—N1—C10—O2179.8 (3)C36—N11—C35—O7−173.6 (3)
C12—N1—C10—O2−3.0 (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—N10−173.2 (3)
C10—N1—C9—N3−175.0 (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—N11−0.5 (4)
C12—N1—C9—C8−170.5 (3)C37—N10—C35—N11−179.1 (3)
C17—C14—C1—C2−61.2 (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—C8−105.8 (3)C26—C21—C22—C23−1.3 (4)
C28—C27—C30—O6−178.1 (3)C20—C21—C22—C23−173.2 (3)
C20—C27—C30—O60.8 (4)C22—C21—C26—C252.1 (4)
C28—C27—C30—N8−0.3 (4)C20—C21—C26—C25173.5 (3)
C20—C27—C30—N8178.6 (2)C21—C22—C23—C24−1.0 (5)
C28—C27—C20—C2161.2 (4)C25—C24—C23—C222.6 (5)
C30—C27—C20—C21−117.7 (3)Cl2—C24—C23—C22−176.9 (2)
C28—C27—C20—C33−76.6 (4)C3—C4—C5—C62.2 (5)
C30—C27—C20—C33104.5 (3)C3—C4—C5—Cl1−178.1 (2)
C35—N10—C34—N12173.9 (3)C17—C14—C15—O4179.5 (3)
C37—N10—C34—N12−7.6 (4)C1—C14—C15—O41.6 (5)
C35—N10—C34—C33−6.8 (4)C17—C14—C15—N4−0.1 (5)
C37—N10—C34—C33171.7 (3)C1—C14—C15—N4−178.1 (3)
N12—C34—C33—C36−172.1 (3)C2—C7—C6—C51.3 (5)
N10—C34—C33—C368.6 (4)C4—C5—C6—C7−3.1 (5)
N12—C34—C33—C205.7 (4)Cl1—C5—C6—C7177.1 (2)
N10—C34—C33—C20−173.5 (2)C17—N5—C16—O3174.9 (3)
O8—C36—C33—C34175.9 (3)C19—N5—C16—O3−2.8 (5)
N11—C36—C33—C34−3.4 (4)C17—N5—C16—N4−5.8 (5)
O8—C36—C33—C20−1.9 (4)C19—N5—C16—N4176.6 (3)
N11—C36—C33—C20178.8 (2)C23—C24—C25—C26−1.9 (5)
C27—C20—C33—C34−86.8 (3)Cl2—C24—C25—C26177.6 (2)
C21—C20—C33—C34134.4 (3)C21—C26—C25—C24−0.5 (5)
C27—C20—C33—C3690.9 (3)O3—C16—N4—C15179.6 (4)
C21—C20—C33—C36−47.8 (4)N5—C16—N4—C150.3 (5)
C16—N5—C17—N6−173.1 (3)O3—C16—N4—C180.2 (6)
C19—N5—C17—N64.4 (4)N5—C16—N4—C18−179.1 (4)
C16—N5—C17—C148.3 (4)O4—C15—N4—C16−177.1 (4)
C19—N5—C17—C14−174.1 (3)C14—C15—N4—C162.6 (5)
C15—C14—C17—N6176.4 (3)O4—C15—N4—C182.3 (6)
C1—C14—C17—N6−5.9 (5)C14—C15—N4—C18−178.0 (4)
C15—C14—C17—N5−5.2 (4)C30—N8—C29—O5176.4 (3)
C1—C14—C17—N5172.5 (3)C32—N8—C29—O5−2.4 (5)
N3—C9—C8—C11172.6 (3)C30—N8—C29—N7−3.1 (4)
N1—C9—C8—C11−9.1 (4)C32—N8—C29—N7178.1 (3)
N3—C9—C8—C1−7.9 (5)C28—N7—C29—O5−171.8 (3)
N1—C9—C8—C1170.4 (3)C31—N7—C29—O56.6 (5)
O1—C11—C8—C9−175.7 (3)C28—N7—C29—N87.7 (4)
N2—C11—C8—C92.7 (4)C31—N7—C29—N8−173.8 (3)
O1—C11—C8—C14.7 (5)C29—N7—C28—N9172.9 (3)
N2—C11—C8—C1−176.8 (3)C31—N7—C28—N9−5.6 (4)
C14—C1—C8—C990.4 (3)C29—N7—C28—C27−8.8 (4)
C2—C1—C8—C9−131.4 (3)C31—N7—C28—C27172.8 (3)
C14—C1—C8—C11−90.1 (3)C30—C27—C28—N9−176.9 (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—N7−174.0 (3)

Hydrogen-bond geometry (Å, °)

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, y−1/2, −z+1/2; (ii) −x+2, y+1/2, −z+1/2; (iii) x−1/2, −y+3/2, −z+1.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: BT5045).

References

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  • Flack, H. D. (1983). Acta Cryst. A39, 876–881.
  • 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.
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