5,6-Dianilino-3-(4-chloro­phen­yl)-3,6-dihydro-1,2,3-triazolo[4,5-d]pyrimidin-7-one

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.

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

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Computing details

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

Crystal data

C22H16ClN7O	F(000) = 888
Mr = 429.87	Dx = 1.417 Mg m^−3
Monoclinic, P21/n	Melting point: 512 K
Hall symbol: -P 2yn	Mo Kα radiation, λ = 0.71073 Å
a = 14.981 (2) Å	Cell parameters from 2384 reflections
b = 7.6973 (12) Å	θ = 2.9–22.0°
c = 17.468 (3) Å	µ = 0.22 mm^−1
β = 90.001 (1)°	T = 292 K
V = 2014.3 (5) Å^3	Block, colorless
Z = 4	0.30 × 0.20 × 0.20 mm

Data collection

Bruker SMART CCD area-detector diffractometer	2595 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.063
Graphite monochromator	θmax = 27.0°, θmin = 1.8°
φ and ω scans	h = −16→19
12017 measured reflections	k = −9→8
4395 independent reflections	l = −22→22

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.050	H-atom parameters constrained
wR(F^2) = 0.125	w = 1/[σ^2(Fo^2) + (0.0602P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 0.90	(Δ/σ)max = 0.001
4395 reflections	Δρmax = 0.43 e Å^−3
281 parameters	Δρmin = −0.37 e Å^−3
0 restraints	Extinction correction: SHELXL97, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0005 (1)

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
C1	0.38608 (16)	−0.0134 (3)	0.40410 (13)	0.0660 (7)
H1	0.3356	0.0482	0.4191	0.079*
C2	0.42405 (17)	0.0163 (3)	0.33326 (14)	0.0700 (7)
H2	0.3994	0.0992	0.3008	0.084*
C3	0.49758 (16)	−0.0753 (3)	0.31059 (12)	0.0553 (6)
C4	0.53438 (14)	−0.1995 (3)	0.35809 (12)	0.0574 (6)
H4	0.5839	−0.2629	0.3423	0.069*
C5	0.49713 (14)	−0.2288 (3)	0.42927 (12)	0.0529 (5)
H5	0.5217	−0.3118	0.4617	0.063*
C6	0.42330 (13)	−0.1347 (3)	0.45223 (11)	0.0458 (5)
C7	0.31902 (13)	−0.0782 (2)	0.56385 (11)	0.0428 (5)
C8	0.30472 (13)	−0.1735 (2)	0.62912 (10)	0.0435 (5)
C9	0.23816 (13)	−0.1207 (3)	0.68341 (11)	0.0461 (5)
C10	0.22188 (13)	0.1289 (3)	0.59387 (11)	0.0431 (5)
C11	0.18987 (15)	0.4089 (2)	0.52738 (11)	0.0474 (5)
C12	0.12057 (17)	0.5253 (3)	0.51824 (13)	0.0639 (6)
H12	0.0709	0.5199	0.5501	0.077*
C13	0.12552 (19)	0.6501 (3)	0.46131 (15)	0.0794 (8)
H13	0.0791	0.7293	0.4556	0.095*
C14	0.1977 (2)	0.6588 (3)	0.41336 (15)	0.0818 (8)
H14	0.1994	0.7401	0.3740	0.098*
C15	0.2674 (2)	0.5456 (3)	0.42422 (15)	0.0762 (8)
H15	0.3176	0.5532	0.3930	0.091*
C16	0.26413 (16)	0.4206 (3)	0.48093 (13)	0.0605 (6)
H16	0.3118	0.3447	0.4878	0.073*
C17	0.03856 (13)	0.0183 (2)	0.68339 (11)	0.0441 (5)
C18	−0.02896 (15)	0.0324 (3)	0.73664 (13)	0.0602 (6)
H18	−0.0183	0.0867	0.7833	0.072*
C19	−0.11271 (17)	−0.0346 (4)	0.72046 (17)	0.0778 (8)
H19	−0.1582	−0.0257	0.7564	0.093*
C20	−0.12868 (17)	−0.1141 (4)	0.65144 (17)	0.0796 (8)
H20	−0.1846	−0.1612	0.6410	0.095*
C21	−0.06210 (18)	−0.1238 (3)	0.59810 (15)	0.0725 (7)
H21	−0.0735	−0.1751	0.5509	0.087*
C22	0.02157 (15)	−0.0587 (3)	0.61338 (12)	0.0572 (6)
H22	0.0665	−0.0664	0.5768	0.069*
Cl1	0.54410 (5)	−0.03631 (9)	0.22126 (4)	0.0831 (3)
N1	0.38419 (10)	−0.1658 (2)	0.52542 (9)	0.0449 (4)
N2	0.40903 (12)	−0.3101 (2)	0.56786 (9)	0.0542 (5)
N3	0.36098 (11)	−0.3130 (2)	0.63005 (9)	0.0526 (5)
N4	0.28118 (11)	0.0749 (2)	0.54387 (9)	0.0450 (4)
N5	0.19470 (10)	0.0323 (2)	0.65726 (9)	0.0430 (4)
N6	0.18025 (11)	0.2832 (2)	0.58623 (9)	0.0514 (4)
H6	0.1428	0.3090	0.6218	0.062*
N7	0.12268 (11)	0.0947 (2)	0.69985 (9)	0.0471 (4)
H7	0.1289	0.1744	0.7339	0.057*
O1	0.21644 (9)	−0.1877 (2)	0.74336 (8)	0.0596 (4)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0724 (16)	0.0689 (15)	0.0566 (14)	0.0251 (13)	0.0151 (12)	0.0129 (12)
C2	0.0919 (19)	0.0628 (16)	0.0552 (14)	0.0149 (14)	0.0136 (13)	0.0148 (12)
C3	0.0644 (15)	0.0531 (13)	0.0485 (12)	−0.0117 (11)	0.0151 (11)	−0.0062 (10)
C4	0.0509 (13)	0.0652 (15)	0.0561 (13)	−0.0002 (11)	0.0074 (11)	−0.0123 (12)
C5	0.0490 (13)	0.0595 (14)	0.0501 (13)	0.0059 (11)	−0.0011 (10)	−0.0013 (10)
C6	0.0486 (12)	0.0471 (12)	0.0417 (11)	0.0012 (10)	0.0015 (9)	−0.0023 (9)
C7	0.0414 (11)	0.0460 (12)	0.0410 (11)	0.0013 (9)	−0.0030 (9)	−0.0003 (9)
C8	0.0440 (12)	0.0450 (12)	0.0416 (11)	0.0042 (9)	−0.0042 (9)	0.0029 (9)
C9	0.0449 (12)	0.0509 (12)	0.0426 (12)	−0.0025 (10)	−0.0072 (10)	0.0025 (10)
C10	0.0457 (12)	0.0434 (12)	0.0402 (11)	0.0007 (9)	−0.0059 (9)	−0.0017 (9)
C11	0.0605 (14)	0.0367 (11)	0.0450 (12)	−0.0012 (10)	−0.0041 (10)	−0.0017 (9)
C12	0.0793 (17)	0.0524 (14)	0.0601 (14)	0.0169 (12)	−0.0004 (12)	0.0033 (11)
C13	0.100 (2)	0.0584 (16)	0.0801 (19)	0.0213 (15)	−0.0128 (17)	0.0084 (14)
C14	0.123 (3)	0.0539 (16)	0.0684 (17)	−0.0027 (17)	−0.0027 (17)	0.0129 (13)
C15	0.097 (2)	0.0550 (15)	0.0763 (18)	−0.0106 (15)	0.0096 (15)	0.0072 (13)
C16	0.0673 (16)	0.0458 (13)	0.0683 (15)	−0.0021 (11)	0.0006 (12)	0.0057 (11)
C17	0.0469 (12)	0.0400 (11)	0.0453 (12)	0.0037 (9)	−0.0035 (10)	0.0005 (9)
C18	0.0558 (15)	0.0733 (16)	0.0514 (13)	0.0028 (12)	0.0022 (11)	−0.0032 (11)
C19	0.0509 (16)	0.101 (2)	0.0818 (19)	0.0005 (14)	0.0065 (13)	0.0108 (16)
C20	0.0591 (17)	0.0811 (19)	0.099 (2)	−0.0111 (14)	−0.0200 (17)	0.0052 (16)
C21	0.0714 (18)	0.0693 (17)	0.0770 (18)	−0.0046 (14)	−0.0246 (15)	−0.0133 (13)
C22	0.0582 (14)	0.0591 (14)	0.0542 (13)	0.0031 (11)	−0.0071 (11)	−0.0111 (11)
Cl1	0.1107 (6)	0.0774 (5)	0.0611 (4)	−0.0119 (4)	0.0326 (4)	−0.0002 (3)
N1	0.0459 (10)	0.0459 (10)	0.0430 (9)	0.0080 (8)	0.0008 (8)	0.0046 (8)
N2	0.0587 (11)	0.0540 (11)	0.0498 (10)	0.0127 (9)	−0.0008 (9)	0.0072 (9)
N3	0.0563 (11)	0.0545 (11)	0.0470 (10)	0.0105 (9)	−0.0017 (9)	0.0084 (8)
N4	0.0477 (10)	0.0436 (10)	0.0436 (9)	0.0075 (8)	0.0015 (8)	0.0033 (7)
N5	0.0456 (10)	0.0454 (10)	0.0381 (9)	0.0027 (8)	0.0012 (7)	−0.0012 (7)
N6	0.0600 (11)	0.0460 (10)	0.0481 (10)	0.0114 (9)	0.0056 (8)	0.0011 (8)
N7	0.0487 (10)	0.0482 (10)	0.0444 (9)	−0.0002 (8)	0.0028 (8)	−0.0136 (8)
O1	0.0608 (10)	0.0694 (10)	0.0486 (9)	0.0056 (8)	0.0073 (7)	0.0144 (8)

Geometric parameters (Å, º)

C1—C6	1.374 (3)	C12—H12	0.9300
C1—C2	1.381 (3)	C13—C14	1.369 (3)
C1—H1	0.9300	C13—H13	0.9300
C2—C3	1.367 (3)	C14—C15	1.374 (4)
C2—H2	0.9300	C14—H14	0.9300
C3—C4	1.381 (3)	C15—C16	1.382 (3)
C3—Cl1	1.735 (2)	C15—H15	0.9300
C4—C5	1.382 (3)	C16—H16	0.9300
C4—H4	0.9300	C17—C18	1.379 (3)
C5—C6	1.382 (3)	C17—C22	1.383 (3)
C5—H5	0.9300	C17—N7	1.420 (2)
C6—N1	1.426 (2)	C18—C19	1.386 (3)
C7—N4	1.353 (2)	C18—H18	0.9300
C7—N1	1.363 (2)	C19—C20	1.373 (4)
C7—C8	1.373 (3)	C19—H19	0.9300
C8—N3	1.365 (2)	C20—C21	1.367 (3)
C8—C9	1.435 (3)	C20—H20	0.9300
C9—O1	1.212 (2)	C21—C22	1.376 (3)
C9—N5	1.421 (2)	C21—H21	0.9300
C10—N4	1.313 (2)	C22—H22	0.9300
C10—N6	1.348 (2)	N1—N2	1.386 (2)
C10—N5	1.395 (2)	N2—N3	1.303 (2)
C11—C16	1.380 (3)	N5—N7	1.396 (2)
C11—C12	1.381 (3)	N6—H6	0.8600
C11—N6	1.419 (2)	N7—H7	0.8600
C12—C13	1.385 (3)
C6—C1—C2	119.6 (2)	C15—C14—H14	120.5
C6—C1—H1	120.2	C14—C15—C16	120.9 (3)
C2—C1—H1	120.2	C14—C15—H15	119.6
C3—C2—C1	120.4 (2)	C16—C15—H15	119.6
C3—C2—H2	119.8	C11—C16—C15	119.7 (2)
C1—C2—H2	119.8	C11—C16—H16	120.1
C2—C3—C4	120.3 (2)	C15—C16—H16	120.1
C2—C3—Cl1	119.68 (19)	C18—C17—C22	119.7 (2)
C4—C3—Cl1	119.99 (18)	C18—C17—N7	118.83 (18)
C3—C4—C5	119.5 (2)	C22—C17—N7	121.33 (19)
C3—C4—H4	120.2	C17—C18—C19	119.8 (2)
C5—C4—H4	120.2	C17—C18—H18	120.1
C4—C5—C6	119.9 (2)	C19—C18—H18	120.1
C4—C5—H5	120.0	C20—C19—C18	120.2 (3)
C6—C5—H5	120.0	C20—C19—H19	119.9
C1—C6—C5	120.2 (2)	C18—C19—H19	119.9
C1—C6—N1	119.71 (18)	C21—C20—C19	119.7 (2)
C5—C6—N1	120.07 (18)	C21—C20—H20	120.1
N4—C7—N1	127.13 (17)	C19—C20—H20	120.1
N4—C7—C8	127.89 (18)	C20—C21—C22	120.8 (2)
N1—C7—C8	104.86 (17)	C20—C21—H21	119.6
N3—C8—C7	109.50 (18)	C22—C21—H21	119.6
N3—C8—C9	130.11 (18)	C21—C22—C17	119.7 (2)
C7—C8—C9	120.40 (18)	C21—C22—H22	120.1
O1—C9—N5	120.50 (19)	C17—C22—H22	120.1
O1—C9—C8	129.57 (19)	C7—N1—N2	108.98 (15)
N5—C9—C8	109.93 (17)	C7—N1—C6	130.72 (16)
N4—C10—N6	121.75 (18)	N2—N1—C6	120.23 (16)
N4—C10—N5	123.80 (18)	N3—N2—N1	108.11 (15)
N6—C10—N5	114.42 (18)	N2—N3—C8	108.55 (16)
C16—C11—C12	119.7 (2)	C10—N4—C7	112.81 (16)
C16—C11—N6	123.53 (19)	C10—N5—N7	117.73 (16)
C12—C11—N6	116.7 (2)	C10—N5—C9	124.29 (17)
C11—C12—C13	119.5 (2)	N7—N5—C9	117.90 (15)
C11—C12—H12	120.2	C10—N6—C11	128.70 (18)
C13—C12—H12	120.2	C10—N6—H6	115.6
C14—C13—C12	121.0 (2)	C11—N6—H6	115.6
C14—C13—H13	119.5	N5—N7—C17	115.84 (15)
C12—C13—H13	119.5	N5—N7—H7	122.1
C13—C14—C15	119.0 (2)	C17—N7—H7	122.1
C13—C14—H14	120.5
C6—C1—C2—C3	0.7 (4)	N4—C7—N1—N2	175.54 (17)
C1—C2—C3—C4	0.4 (4)	C8—C7—N1—N2	−0.7 (2)
C1—C2—C3—Cl1	179.83 (19)	N4—C7—N1—C6	−7.5 (3)
C2—C3—C4—C5	−1.0 (3)	C8—C7—N1—C6	176.20 (17)
Cl1—C3—C4—C5	179.63 (16)	C1—C6—N1—C7	−9.8 (3)
C3—C4—C5—C6	0.3 (3)	C5—C6—N1—C7	171.53 (19)
C2—C1—C6—C5	−1.3 (3)	C1—C6—N1—N2	166.80 (19)
C2—C1—C6—N1	−180.0 (2)	C5—C6—N1—N2	−11.8 (3)
C4—C5—C6—C1	0.8 (3)	C7—N1—N2—N3	0.3 (2)
C4—C5—C6—N1	179.42 (17)	C6—N1—N2—N3	−177.00 (16)
N4—C7—C8—N3	−175.33 (17)	N1—N2—N3—C8	0.3 (2)
N1—C7—C8—N3	0.9 (2)	C7—C8—N3—N2	−0.7 (2)
N4—C7—C8—C9	5.0 (3)	C9—C8—N3—N2	178.91 (19)
N1—C7—C8—C9	−178.79 (16)	N6—C10—N4—C7	176.47 (16)
N3—C8—C9—O1	0.3 (4)	N5—C10—N4—C7	−5.4 (3)
C7—C8—C9—O1	179.94 (19)	N1—C7—N4—C10	−178.09 (18)
N3—C8—C9—N5	−178.88 (18)	C8—C7—N4—C10	−2.7 (3)
C7—C8—C9—N5	0.7 (2)	N4—C10—N5—N7	−171.47 (16)
C16—C11—C12—C13	1.5 (3)	N6—C10—N5—N7	6.8 (2)
N6—C11—C12—C13	−179.4 (2)	N4—C10—N5—C9	11.7 (3)
C11—C12—C13—C14	0.7 (4)	N6—C10—N5—C9	−170.05 (16)
C12—C13—C14—C15	−2.5 (4)	O1—C9—N5—C10	172.35 (17)
C13—C14—C15—C16	2.2 (4)	C8—C9—N5—C10	−8.4 (2)
C12—C11—C16—C15	−1.8 (3)	O1—C9—N5—N7	−4.5 (3)
N6—C11—C16—C15	179.10 (19)	C8—C9—N5—N7	174.82 (15)
C14—C15—C16—C11	0.0 (4)	N4—C10—N6—C11	0.7 (3)
C22—C17—C18—C19	1.6 (3)	N5—C10—N6—C11	−177.63 (17)
N7—C17—C18—C19	177.3 (2)	C16—C11—N6—C10	−22.1 (3)
C17—C18—C19—C20	−0.3 (4)	C12—C11—N6—C10	158.80 (19)
C18—C19—C20—C21	−1.3 (4)	C10—N5—N7—C17	98.39 (19)
C19—C20—C21—C22	1.6 (4)	C9—N5—N7—C17	−84.6 (2)
C20—C21—C22—C17	−0.3 (4)	C18—C17—N7—N5	160.60 (17)
C18—C17—C22—C21	−1.3 (3)	C22—C17—N7—N5	−23.9 (3)
N7—C17—C22—C21	−176.85 (19)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N6—H6···N7	0.86	2.16	2.606 (2)	112
N7—H7···N3^i	0.86	2.38	3.065 (2)	137
N7—H7···O1^i	0.86	2.58	3.098 (2)	120
C1—H1···N4	0.93	2.34	2.982 (3)	126
C5—H5···N2	0.93	2.51	2.827 (3)	100
C16—H16···N4	0.93	2.34	2.891 (3)	118

Symmetry code: (i) −x+1/2, y+1/2, −z+3/2.