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In the title compound, C22H16ClN7O, all ring atoms in the triazolopyrimidinone system are almost coplanar. The packing of the mol­ecules in the crystal structure is mainly a result of π–π and N—H...N/O hydrogen-bonding inter­actions, forming a three-dimensional network.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805024074/ob6548sup1.cif
Contains datablocks global, 2

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536805024074/ob65482sup2.hkl
Contains datablock 2

CCDC reference: 283967

Key indicators

  • Single-crystal X-ray study
  • T = 292 K
  • Mean [sigma](C-C)= 0.003 Å
  • R factor = 0.050
  • wR factor = 0.125
  • Data-to-parameter ratio = 15.6

checkCIF/PLATON results

No syntax errors found


No errors found in this datablock

Computing details top

Data collection: SMART (Bruker, 2001); cell refinement: SMART; data reduction: SAINT-Plus (Bruker, 2001); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 2001); software used to prepare material for publication: SHELXTL.

5,6-Dianilino-3-(4-chlorophenyl)-3,6-dihydro-1,2,3-triazolo[4,5-d]pyrimidin- 7-one top
Crystal data top
C22H16ClN7OF(000) = 888
Mr = 429.87Dx = 1.417 Mg m3
Monoclinic, P21/nMelting point: 512 K
Hall symbol: -P 2ynMo Kα radiation, λ = 0.71073 Å
a = 14.981 (2) ÅCell parameters from 2384 reflections
b = 7.6973 (12) Åθ = 2.9–22.0°
c = 17.468 (3) ŵ = 0.22 mm1
β = 90.001 (1)°T = 292 K
V = 2014.3 (5) Å3Block, colorless
Z = 40.30 × 0.20 × 0.20 mm
Data collection top
Bruker SMART CCD area-detector
diffractometer
2595 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.063
Graphite monochromatorθmax = 27.0°, θmin = 1.8°
φ and ω scansh = 1619
12017 measured reflectionsk = 98
4395 independent reflectionsl = 2222
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)] = 0.050H-atom parameters constrained
wR(F2) = 0.125 w = 1/[σ2(Fo2) + (0.0602P)2]
where P = (Fo2 + 2Fc2)/3
S = 0.90(Δ/σ)max = 0.001
4395 reflectionsΔρmax = 0.43 e Å3
281 parametersΔρmin = 0.37 e Å3
0 restraintsExtinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0005 (1)
Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
C10.38608 (16)0.0134 (3)0.40410 (13)0.0660 (7)
H10.33560.04820.41910.079*
C20.42405 (17)0.0163 (3)0.33326 (14)0.0700 (7)
H20.39940.09920.30080.084*
C30.49758 (16)0.0753 (3)0.31059 (12)0.0553 (6)
C40.53438 (14)0.1995 (3)0.35809 (12)0.0574 (6)
H40.58390.26290.34230.069*
C50.49713 (14)0.2288 (3)0.42927 (12)0.0529 (5)
H50.52170.31180.46170.063*
C60.42330 (13)0.1347 (3)0.45223 (11)0.0458 (5)
C70.31902 (13)0.0782 (2)0.56385 (11)0.0428 (5)
C80.30472 (13)0.1735 (2)0.62912 (10)0.0435 (5)
C90.23816 (13)0.1207 (3)0.68341 (11)0.0461 (5)
C100.22188 (13)0.1289 (3)0.59387 (11)0.0431 (5)
C110.18987 (15)0.4089 (2)0.52738 (11)0.0474 (5)
C120.12057 (17)0.5253 (3)0.51824 (13)0.0639 (6)
H120.07090.51990.55010.077*
C130.12552 (19)0.6501 (3)0.46131 (15)0.0794 (8)
H130.07910.72930.45560.095*
C140.1977 (2)0.6588 (3)0.41336 (15)0.0818 (8)
H140.19940.74010.37400.098*
C150.2674 (2)0.5456 (3)0.42422 (15)0.0762 (8)
H150.31760.55320.39300.091*
C160.26413 (16)0.4206 (3)0.48093 (13)0.0605 (6)
H160.31180.34470.48780.073*
C170.03856 (13)0.0183 (2)0.68339 (11)0.0441 (5)
C180.02896 (15)0.0324 (3)0.73664 (13)0.0602 (6)
H180.01830.08670.78330.072*
C190.11271 (17)0.0346 (4)0.72046 (17)0.0778 (8)
H190.15820.02570.75640.093*
C200.12868 (17)0.1141 (4)0.65144 (17)0.0796 (8)
H200.18460.16120.64100.095*
C210.06210 (18)0.1238 (3)0.59810 (15)0.0725 (7)
H210.07350.17510.55090.087*
C220.02157 (15)0.0587 (3)0.61338 (12)0.0572 (6)
H220.06650.06640.57680.069*
Cl10.54410 (5)0.03631 (9)0.22126 (4)0.0831 (3)
N10.38419 (10)0.1658 (2)0.52542 (9)0.0449 (4)
N20.40903 (12)0.3101 (2)0.56786 (9)0.0542 (5)
N30.36098 (11)0.3130 (2)0.63005 (9)0.0526 (5)
N40.28118 (11)0.0749 (2)0.54387 (9)0.0450 (4)
N50.19470 (10)0.0323 (2)0.65726 (9)0.0430 (4)
N60.18025 (11)0.2832 (2)0.58623 (9)0.0514 (4)
H60.14280.30900.62180.062*
N70.12268 (11)0.0947 (2)0.69985 (9)0.0471 (4)
H70.12890.17440.73390.057*
O10.21644 (9)0.1877 (2)0.74336 (8)0.0596 (4)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0724 (16)0.0689 (15)0.0566 (14)0.0251 (13)0.0151 (12)0.0129 (12)
C20.0919 (19)0.0628 (16)0.0552 (14)0.0149 (14)0.0136 (13)0.0148 (12)
C30.0644 (15)0.0531 (13)0.0485 (12)0.0117 (11)0.0151 (11)0.0062 (10)
C40.0509 (13)0.0652 (15)0.0561 (13)0.0002 (11)0.0074 (11)0.0123 (12)
C50.0490 (13)0.0595 (14)0.0501 (13)0.0059 (11)0.0011 (10)0.0013 (10)
C60.0486 (12)0.0471 (12)0.0417 (11)0.0012 (10)0.0015 (9)0.0023 (9)
C70.0414 (11)0.0460 (12)0.0410 (11)0.0013 (9)0.0030 (9)0.0003 (9)
C80.0440 (12)0.0450 (12)0.0416 (11)0.0042 (9)0.0042 (9)0.0029 (9)
C90.0449 (12)0.0509 (12)0.0426 (12)0.0025 (10)0.0072 (10)0.0025 (10)
C100.0457 (12)0.0434 (12)0.0402 (11)0.0007 (9)0.0059 (9)0.0017 (9)
C110.0605 (14)0.0367 (11)0.0450 (12)0.0012 (10)0.0041 (10)0.0017 (9)
C120.0793 (17)0.0524 (14)0.0601 (14)0.0169 (12)0.0004 (12)0.0033 (11)
C130.100 (2)0.0584 (16)0.0801 (19)0.0213 (15)0.0128 (17)0.0084 (14)
C140.123 (3)0.0539 (16)0.0684 (17)0.0027 (17)0.0027 (17)0.0129 (13)
C150.097 (2)0.0550 (15)0.0763 (18)0.0106 (15)0.0096 (15)0.0072 (13)
C160.0673 (16)0.0458 (13)0.0683 (15)0.0021 (11)0.0006 (12)0.0057 (11)
C170.0469 (12)0.0400 (11)0.0453 (12)0.0037 (9)0.0035 (10)0.0005 (9)
C180.0558 (15)0.0733 (16)0.0514 (13)0.0028 (12)0.0022 (11)0.0032 (11)
C190.0509 (16)0.101 (2)0.0818 (19)0.0005 (14)0.0065 (13)0.0108 (16)
C200.0591 (17)0.0811 (19)0.099 (2)0.0111 (14)0.0200 (17)0.0052 (16)
C210.0714 (18)0.0693 (17)0.0770 (18)0.0046 (14)0.0246 (15)0.0133 (13)
C220.0582 (14)0.0591 (14)0.0542 (13)0.0031 (11)0.0071 (11)0.0111 (11)
Cl10.1107 (6)0.0774 (5)0.0611 (4)0.0119 (4)0.0326 (4)0.0002 (3)
N10.0459 (10)0.0459 (10)0.0430 (9)0.0080 (8)0.0008 (8)0.0046 (8)
N20.0587 (11)0.0540 (11)0.0498 (10)0.0127 (9)0.0008 (9)0.0072 (9)
N30.0563 (11)0.0545 (11)0.0470 (10)0.0105 (9)0.0017 (9)0.0084 (8)
N40.0477 (10)0.0436 (10)0.0436 (9)0.0075 (8)0.0015 (8)0.0033 (7)
N50.0456 (10)0.0454 (10)0.0381 (9)0.0027 (8)0.0012 (7)0.0012 (7)
N60.0600 (11)0.0460 (10)0.0481 (10)0.0114 (9)0.0056 (8)0.0011 (8)
N70.0487 (10)0.0482 (10)0.0444 (9)0.0002 (8)0.0028 (8)0.0136 (8)
O10.0608 (10)0.0694 (10)0.0486 (9)0.0056 (8)0.0073 (7)0.0144 (8)
Geometric parameters (Å, º) top
C1—C61.374 (3)C12—H120.9300
C1—C21.381 (3)C13—C141.369 (3)
C1—H10.9300C13—H130.9300
C2—C31.367 (3)C14—C151.374 (4)
C2—H20.9300C14—H140.9300
C3—C41.381 (3)C15—C161.382 (3)
C3—Cl11.735 (2)C15—H150.9300
C4—C51.382 (3)C16—H160.9300
C4—H40.9300C17—C181.379 (3)
C5—C61.382 (3)C17—C221.383 (3)
C5—H50.9300C17—N71.420 (2)
C6—N11.426 (2)C18—C191.386 (3)
C7—N41.353 (2)C18—H180.9300
C7—N11.363 (2)C19—C201.373 (4)
C7—C81.373 (3)C19—H190.9300
C8—N31.365 (2)C20—C211.367 (3)
C8—C91.435 (3)C20—H200.9300
C9—O11.212 (2)C21—C221.376 (3)
C9—N51.421 (2)C21—H210.9300
C10—N41.313 (2)C22—H220.9300
C10—N61.348 (2)N1—N21.386 (2)
C10—N51.395 (2)N2—N31.303 (2)
C11—C161.380 (3)N5—N71.396 (2)
C11—C121.381 (3)N6—H60.8600
C11—N61.419 (2)N7—H70.8600
C12—C131.385 (3)
C6—C1—C2119.6 (2)C15—C14—H14120.5
C6—C1—H1120.2C14—C15—C16120.9 (3)
C2—C1—H1120.2C14—C15—H15119.6
C3—C2—C1120.4 (2)C16—C15—H15119.6
C3—C2—H2119.8C11—C16—C15119.7 (2)
C1—C2—H2119.8C11—C16—H16120.1
C2—C3—C4120.3 (2)C15—C16—H16120.1
C2—C3—Cl1119.68 (19)C18—C17—C22119.7 (2)
C4—C3—Cl1119.99 (18)C18—C17—N7118.83 (18)
C3—C4—C5119.5 (2)C22—C17—N7121.33 (19)
C3—C4—H4120.2C17—C18—C19119.8 (2)
C5—C4—H4120.2C17—C18—H18120.1
C4—C5—C6119.9 (2)C19—C18—H18120.1
C4—C5—H5120.0C20—C19—C18120.2 (3)
C6—C5—H5120.0C20—C19—H19119.9
C1—C6—C5120.2 (2)C18—C19—H19119.9
C1—C6—N1119.71 (18)C21—C20—C19119.7 (2)
C5—C6—N1120.07 (18)C21—C20—H20120.1
N4—C7—N1127.13 (17)C19—C20—H20120.1
N4—C7—C8127.89 (18)C20—C21—C22120.8 (2)
N1—C7—C8104.86 (17)C20—C21—H21119.6
N3—C8—C7109.50 (18)C22—C21—H21119.6
N3—C8—C9130.11 (18)C21—C22—C17119.7 (2)
C7—C8—C9120.40 (18)C21—C22—H22120.1
O1—C9—N5120.50 (19)C17—C22—H22120.1
O1—C9—C8129.57 (19)C7—N1—N2108.98 (15)
N5—C9—C8109.93 (17)C7—N1—C6130.72 (16)
N4—C10—N6121.75 (18)N2—N1—C6120.23 (16)
N4—C10—N5123.80 (18)N3—N2—N1108.11 (15)
N6—C10—N5114.42 (18)N2—N3—C8108.55 (16)
C16—C11—C12119.7 (2)C10—N4—C7112.81 (16)
C16—C11—N6123.53 (19)C10—N5—N7117.73 (16)
C12—C11—N6116.7 (2)C10—N5—C9124.29 (17)
C11—C12—C13119.5 (2)N7—N5—C9117.90 (15)
C11—C12—H12120.2C10—N6—C11128.70 (18)
C13—C12—H12120.2C10—N6—H6115.6
C14—C13—C12121.0 (2)C11—N6—H6115.6
C14—C13—H13119.5N5—N7—C17115.84 (15)
C12—C13—H13119.5N5—N7—H7122.1
C13—C14—C15119.0 (2)C17—N7—H7122.1
C13—C14—H14120.5
C6—C1—C2—C30.7 (4)N4—C7—N1—N2175.54 (17)
C1—C2—C3—C40.4 (4)C8—C7—N1—N20.7 (2)
C1—C2—C3—Cl1179.83 (19)N4—C7—N1—C67.5 (3)
C2—C3—C4—C51.0 (3)C8—C7—N1—C6176.20 (17)
Cl1—C3—C4—C5179.63 (16)C1—C6—N1—C79.8 (3)
C3—C4—C5—C60.3 (3)C5—C6—N1—C7171.53 (19)
C2—C1—C6—C51.3 (3)C1—C6—N1—N2166.80 (19)
C2—C1—C6—N1180.0 (2)C5—C6—N1—N211.8 (3)
C4—C5—C6—C10.8 (3)C7—N1—N2—N30.3 (2)
C4—C5—C6—N1179.42 (17)C6—N1—N2—N3177.00 (16)
N4—C7—C8—N3175.33 (17)N1—N2—N3—C80.3 (2)
N1—C7—C8—N30.9 (2)C7—C8—N3—N20.7 (2)
N4—C7—C8—C95.0 (3)C9—C8—N3—N2178.91 (19)
N1—C7—C8—C9178.79 (16)N6—C10—N4—C7176.47 (16)
N3—C8—C9—O10.3 (4)N5—C10—N4—C75.4 (3)
C7—C8—C9—O1179.94 (19)N1—C7—N4—C10178.09 (18)
N3—C8—C9—N5178.88 (18)C8—C7—N4—C102.7 (3)
C7—C8—C9—N50.7 (2)N4—C10—N5—N7171.47 (16)
C16—C11—C12—C131.5 (3)N6—C10—N5—N76.8 (2)
N6—C11—C12—C13179.4 (2)N4—C10—N5—C911.7 (3)
C11—C12—C13—C140.7 (4)N6—C10—N5—C9170.05 (16)
C12—C13—C14—C152.5 (4)O1—C9—N5—C10172.35 (17)
C13—C14—C15—C162.2 (4)C8—C9—N5—C108.4 (2)
C12—C11—C16—C151.8 (3)O1—C9—N5—N74.5 (3)
N6—C11—C16—C15179.10 (19)C8—C9—N5—N7174.82 (15)
C14—C15—C16—C110.0 (4)N4—C10—N6—C110.7 (3)
C22—C17—C18—C191.6 (3)N5—C10—N6—C11177.63 (17)
N7—C17—C18—C19177.3 (2)C16—C11—N6—C1022.1 (3)
C17—C18—C19—C200.3 (4)C12—C11—N6—C10158.80 (19)
C18—C19—C20—C211.3 (4)C10—N5—N7—C1798.39 (19)
C19—C20—C21—C221.6 (4)C9—N5—N7—C1784.6 (2)
C20—C21—C22—C170.3 (4)C18—C17—N7—N5160.60 (17)
C18—C17—C22—C211.3 (3)C22—C17—N7—N523.9 (3)
N7—C17—C22—C21176.85 (19)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N6—H6···N70.862.162.606 (2)112
N7—H7···N3i0.862.383.065 (2)137
N7—H7···O1i0.862.583.098 (2)120
C1—H1···N40.932.342.982 (3)126
C5—H5···N20.932.512.827 (3)100
C16—H16···N40.932.342.891 (3)118
Symmetry code: (i) x+1/2, y+1/2, z+3/2.
 

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