1-(Pyridin-4-yl)-3-(2,4,6-tri­chloro­phen­yl)benz[4,5]imidazo[1,2-d][1,2,4]triazin-4(3H)-one

In the title compound, C₂₀H₁₀Cl₃N₅O, the 13-membered ring system makes dihedral angles of 78.64 (9)° with the tri­chloro­phenyl ring and 62.60 (10)° with the pyridine ring. The crystal packing is dominated by π–π inter­actions between the 13-membered ring systems [centroid–centroid distance = 3.6655 (11)°].

Key indicators

• Single-crystal X-ray study
• T = 193 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.041
• wR factor = 0.113
• Data-to-parameter ratio = 17.5

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT906_ALERT_3_C Large K value in the Analysis of Variance ......      2.215 Check
PLAT911_ALERT_3_C Missing # FCF Refl Between THmin & STh/L=  0.600          3 Report

Alert level G
PLAT128_ALERT_4_G Alternate Setting for Input Space Group     C2/c       I2/a Note
PLAT910_ALERT_3_G Missing # of FCF Reflection(s) Below Theta(Min)           2 Note
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L=  0.600         18 Note
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density          12 Note

   0 ALERT level A = Most likely a serious problem - resolve or explain
   0 ALERT level B = A potentially serious problem, consider carefully
   2 ALERT level C = Check. Ensure it is not caused by an omission or oversight
   4 ALERT level G = General information/check it is not something unexpected

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   1 ALERT type 2 Indicator that the structure model may be wrong or deficient
   3 ALERT type 3 Indicator that the structure quality may be low
   2 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check


checkCIF publication errors

Alert level A
PUBL024_ALERT_1_A The number of authors is greater than 5.
              Please specify the role of each of the co-authors
              for your paper.

   1 ALERT level A = Data missing that is essential or data in wrong format
   0 ALERT level G = General alerts. Data that may be required is missing

---

Computing details

Data collection: X-AREA (Stoe & Cie, 2006a); cell refinement: X-AREA (Stoe & Cie, 2006); data reduction: X-RED32 (Stoe & Cie, 2006); program(s) used to solve structure: SIR2004 (Altomare et al., 1995); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015); software used to prepare material for publication: SHELXL2014 (Sheldrick, 2015).

1-(Pyridin-4-yl)-3-(2,4,6-trichlorophenyl)benz[4,5]imidazo[1,2-d][1,2,4]triazin-4(3H)-one

Crystal data

C20H10Cl3N5O	F(000) = 1792
Mr = 442.68	Dx = 1.583 Mg m^−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
a = 19.5521 (12) Å	Cell parameters from 12681 reflections
b = 15.1072 (5) Å	θ = 2.6–28.3°
c = 15.5543 (9) Å	µ = 0.52 mm^−1
β = 126.057 (4)°	T = 193 K
V = 3714.2 (4) Å^3	Plate, colourless
Z = 8	0.35 × 0.21 × 0.20 mm

Data collection

Stoe IPDS 2T diffractometer	3437 reflections with I > 2σ(I)
Radiation source: sealed X-ray tube, 12 x 0.4 mm long-fine focus	Rint = 0.022
Detector resolution: 6.67 pixels mm^-1	θmax = 28.2°, θmin = 2.6°
rotation method scans	h = −25→20
11381 measured reflections	k = −20→18
4574 independent reflections	l = −20→20

Refinement

Refinement on F^2	0 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.041	H-atom parameters constrained
wR(F^2) = 0.113	w = 1/[σ^2(Fo^2) + (0.051P)^2 + 3.9605P] where P = (Fo^2 + 2Fc^2)/3
S = 1.04	(Δ/σ)max < 0.001
4574 reflections	Δρmax = 0.89 e Å^−3
262 parameters	Δρmin = −0.98 e Å^−3

Special details

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

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
Cl1	0.32853 (6)	0.12694 (4)	0.13199 (6)	0.0620 (2)
Cl2	0.43245 (5)	0.39787 (5)	0.01324 (6)	0.0644 (2)
Cl3	0.34201 (5)	0.45705 (4)	0.27335 (5)	0.05540 (18)
O1	0.18165 (10)	0.29896 (13)	0.14004 (12)	0.0496 (4)
N1	0.27697 (10)	0.17190 (11)	0.37941 (11)	0.0276 (3)
N2	0.37972 (10)	0.20832 (11)	0.35279 (12)	0.0300 (3)
N3	0.31780 (11)	0.25749 (12)	0.26496 (12)	0.0336 (4)
C1	0.35845 (11)	0.16738 (12)	0.40623 (13)	0.0272 (4)
C4	0.23280 (13)	0.25910 (15)	0.22150 (14)	0.0359 (4)
C5	0.21233 (12)	0.21304 (14)	0.28666 (14)	0.0316 (4)
N6	0.13953 (10)	0.21308 (12)	0.27260 (12)	0.0346 (4)
C7	0.15680 (12)	0.17234 (13)	0.36360 (14)	0.0303 (4)
C8	0.10192 (12)	0.16098 (14)	0.39282 (15)	0.0336 (4)
H8	0.0442	0.1782	0.3469	0.040*
C9	0.13499 (13)	0.12388 (14)	0.49083 (15)	0.0345 (4)
H9	0.0994	0.1157	0.5131	0.041*
C10	0.21982 (13)	0.09796 (14)	0.55831 (15)	0.0338 (4)
H10	0.2401	0.0722	0.6251	0.041*
C11	0.27507 (12)	0.10858 (13)	0.53118 (14)	0.0305 (4)
H11	0.3327	0.0910	0.5775	0.037*
C12	0.24185 (11)	0.14642 (12)	0.43222 (13)	0.0271 (4)
C13	0.42283 (11)	0.11300 (12)	0.49832 (13)	0.0264 (4)
C14	0.40997 (13)	0.02308 (13)	0.50356 (17)	0.0344 (4)
H14	0.3595	−0.0054	0.4479	0.041*
C15	0.47300 (15)	−0.02355 (15)	0.59233 (19)	0.0429 (5)
H15	0.4647	−0.0851	0.5954	0.051*
N16	0.54470 (12)	0.01269 (14)	0.67379 (15)	0.0459 (5)
C17	0.55553 (14)	0.09801 (16)	0.66609 (16)	0.0415 (5)
H17	0.6064	0.1248	0.7231	0.050*
C18	0.49758 (12)	0.15087 (13)	0.58041 (14)	0.0317 (4)
H18	0.5091	0.2116	0.5783	0.038*
C19	0.34486 (13)	0.29350 (14)	0.20419 (15)	0.0344 (4)
C20	0.35514 (14)	0.23695 (14)	0.14171 (16)	0.0389 (5)
C21	0.38352 (15)	0.26848 (16)	0.08389 (18)	0.0442 (5)
H21	0.3918	0.2295	0.0428	0.053*
C22	0.39927 (15)	0.35738 (17)	0.08770 (18)	0.0441 (5)
C23	0.38711 (16)	0.41627 (16)	0.14555 (17)	0.0440 (5)
H23	0.3971	0.4778	0.1455	0.053*
C24	0.35979 (14)	0.38281 (15)	0.20364 (16)	0.0381 (5)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cl1	0.1095 (6)	0.0359 (3)	0.0802 (4)	0.0179 (3)	0.0779 (5)	0.0153 (3)
Cl2	0.0942 (5)	0.0645 (4)	0.0793 (4)	0.0099 (4)	0.0760 (4)	0.0183 (3)
Cl3	0.0916 (5)	0.0457 (3)	0.0555 (3)	0.0027 (3)	0.0581 (4)	0.0002 (3)
O1	0.0444 (9)	0.0751 (12)	0.0349 (7)	0.0228 (8)	0.0265 (7)	0.0253 (7)
N1	0.0283 (7)	0.0344 (8)	0.0220 (6)	0.0037 (6)	0.0159 (6)	0.0034 (6)
N2	0.0303 (8)	0.0341 (8)	0.0271 (7)	0.0074 (7)	0.0178 (6)	0.0073 (6)
N3	0.0364 (9)	0.0420 (9)	0.0293 (7)	0.0113 (7)	0.0232 (7)	0.0133 (7)
C1	0.0289 (9)	0.0283 (9)	0.0263 (8)	0.0017 (7)	0.0174 (7)	0.0009 (7)
C4	0.0377 (11)	0.0473 (12)	0.0277 (8)	0.0121 (9)	0.0220 (8)	0.0099 (8)
C5	0.0300 (9)	0.0411 (11)	0.0231 (8)	0.0076 (8)	0.0152 (7)	0.0055 (7)
N6	0.0319 (8)	0.0461 (10)	0.0274 (7)	0.0078 (7)	0.0182 (7)	0.0063 (7)
C7	0.0330 (9)	0.0339 (10)	0.0265 (8)	0.0025 (8)	0.0189 (7)	0.0001 (7)
C8	0.0314 (9)	0.0405 (11)	0.0323 (9)	0.0027 (8)	0.0206 (8)	−0.0006 (8)
C9	0.0382 (10)	0.0396 (11)	0.0357 (9)	−0.0021 (9)	0.0272 (9)	−0.0030 (8)
C10	0.0417 (11)	0.0360 (10)	0.0295 (9)	0.0002 (9)	0.0241 (8)	0.0017 (8)
C11	0.0335 (9)	0.0341 (10)	0.0252 (8)	0.0027 (8)	0.0181 (7)	0.0017 (7)
C12	0.0300 (9)	0.0302 (9)	0.0253 (8)	0.0002 (7)	0.0185 (7)	−0.0011 (7)
C13	0.0280 (8)	0.0286 (9)	0.0264 (8)	0.0030 (7)	0.0181 (7)	0.0038 (7)
C14	0.0325 (10)	0.0297 (10)	0.0456 (10)	0.0014 (8)	0.0256 (9)	0.0025 (8)
C15	0.0469 (12)	0.0328 (11)	0.0631 (14)	0.0107 (9)	0.0402 (12)	0.0177 (10)
N16	0.0430 (10)	0.0521 (12)	0.0448 (10)	0.0175 (9)	0.0270 (9)	0.0224 (9)
C17	0.0361 (11)	0.0492 (13)	0.0293 (9)	0.0055 (10)	0.0137 (8)	0.0048 (9)
C18	0.0321 (9)	0.0322 (10)	0.0289 (9)	0.0027 (8)	0.0169 (8)	0.0020 (7)
C19	0.0394 (10)	0.0410 (11)	0.0321 (9)	0.0118 (9)	0.0262 (8)	0.0125 (8)
C20	0.0501 (12)	0.0373 (11)	0.0414 (10)	0.0165 (9)	0.0336 (10)	0.0152 (9)
C21	0.0599 (14)	0.0460 (13)	0.0458 (11)	0.0210 (11)	0.0416 (11)	0.0167 (10)
C22	0.0533 (13)	0.0531 (14)	0.0437 (11)	0.0105 (11)	0.0384 (11)	0.0161 (10)
C23	0.0576 (14)	0.0431 (13)	0.0443 (11)	0.0027 (10)	0.0373 (11)	0.0078 (9)
C24	0.0450 (12)	0.0444 (12)	0.0328 (9)	0.0070 (9)	0.0273 (9)	0.0064 (8)

Geometric parameters (Å, º)

Cl1—C20	1.721 (2)	C10—H10	0.9500
Cl2—C22	1.738 (2)	C11—C12	1.393 (2)
Cl3—C24	1.732 (2)	C11—H11	0.9500
O1—C4	1.215 (2)	C13—C18	1.377 (3)
N1—C5	1.385 (2)	C13—C14	1.393 (3)
N1—C1	1.391 (2)	C14—C15	1.385 (3)
N1—C12	1.400 (2)	C14—H14	0.9500
N2—C1	1.286 (2)	C15—N16	1.334 (3)
N2—N3	1.392 (2)	C15—H15	0.9500
N3—C4	1.377 (3)	N16—C17	1.323 (3)
N3—C19	1.435 (2)	C17—C18	1.386 (3)
C1—C13	1.479 (2)	C17—H17	0.9500
C4—C5	1.466 (3)	C18—H18	0.9500
C5—N6	1.307 (2)	C19—C24	1.382 (3)
N6—C7	1.391 (2)	C19—C20	1.395 (3)
C7—C8	1.400 (3)	C20—C21	1.390 (3)
C7—C12	1.403 (3)	C21—C22	1.371 (3)
C8—C9	1.377 (3)	C21—H21	0.9500
C8—H8	0.9500	C22—C23	1.382 (3)
C9—C10	1.399 (3)	C23—C24	1.388 (3)
C9—H9	0.9500	C23—H23	0.9500
C10—C11	1.381 (3)
C5—N1—C1	121.08 (15)	C18—C13—C14	118.72 (17)
C5—N1—C12	105.83 (15)	C18—C13—C1	120.06 (17)
C1—N1—C12	132.97 (15)	C14—C13—C1	121.22 (17)
C1—N2—N3	117.77 (16)	C15—C14—C13	117.98 (19)
C4—N3—N2	126.33 (16)	C15—C14—H14	121.0
C4—N3—C19	118.44 (15)	C13—C14—H14	121.0
N2—N3—C19	113.84 (15)	N16—C15—C14	124.0 (2)
N2—C1—N1	122.12 (16)	N16—C15—H15	118.0
N2—C1—C13	118.59 (16)	C14—C15—H15	118.0
N1—C1—C13	119.29 (15)	C17—N16—C15	116.66 (18)
O1—C4—N3	122.37 (18)	N16—C17—C18	124.4 (2)
O1—C4—C5	124.34 (19)	N16—C17—H17	117.8
N3—C4—C5	113.19 (15)	C18—C17—H17	117.8
N6—C5—N1	114.25 (16)	C13—C18—C17	118.23 (19)
N6—C5—C4	126.71 (17)	C13—C18—H18	120.9
N1—C5—C4	118.69 (17)	C17—C18—H18	120.9
C5—N6—C7	103.98 (15)	C24—C19—C20	118.44 (18)
N6—C7—C8	127.68 (18)	C24—C19—N3	122.39 (18)
N6—C7—C12	111.52 (16)	C20—C19—N3	119.16 (19)
C8—C7—C12	120.69 (17)	C21—C20—C19	121.1 (2)
C9—C8—C7	117.32 (18)	C21—C20—Cl1	119.30 (17)
C9—C8—H8	121.3	C19—C20—Cl1	119.51 (16)
C7—C8—H8	121.3	C22—C21—C20	118.2 (2)
C8—C9—C10	121.43 (18)	C22—C21—H21	120.9
C8—C9—H9	119.3	C20—C21—H21	120.9
C10—C9—H9	119.3	C21—C22—C23	122.57 (19)
C11—C10—C9	122.24 (17)	C21—C22—Cl2	118.58 (17)
C11—C10—H10	118.9	C23—C22—Cl2	118.82 (19)
C9—C10—H10	118.9	C22—C23—C24	118.0 (2)
C10—C11—C12	116.45 (17)	C22—C23—H23	121.0
C10—C11—H11	121.8	C24—C23—H23	121.0
C12—C11—H11	121.8	C19—C24—C23	121.6 (2)
C11—C12—N1	133.68 (17)	C19—C24—Cl3	120.51 (15)
C11—C12—C7	121.88 (17)	C23—C24—Cl3	117.90 (18)
N1—C12—C7	104.36 (15)
C1—N2—N3—C4	−7.9 (3)	C8—C7—C12—C11	0.1 (3)
C1—N2—N3—C19	−174.11 (18)	N6—C7—C12—N1	−0.7 (2)
N3—N2—C1—N1	−0.7 (3)	C8—C7—C12—N1	−177.00 (18)
N3—N2—C1—C13	178.54 (16)	N2—C1—C13—C18	57.3 (2)
C5—N1—C1—N2	7.2 (3)	N1—C1—C13—C18	−123.43 (19)
C12—N1—C1—N2	−168.14 (19)	N2—C1—C13—C14	−121.9 (2)
C5—N1—C1—C13	−172.08 (17)	N1—C1—C13—C14	57.3 (2)
C12—N1—C1—C13	12.6 (3)	C18—C13—C14—C15	0.8 (3)
N2—N3—C4—O1	−174.6 (2)	C1—C13—C14—C15	−179.91 (17)
C19—N3—C4—O1	−9.0 (3)	C13—C14—C15—N16	1.0 (3)
N2—N3—C4—C5	8.9 (3)	C14—C15—N16—C17	−1.7 (3)
C19—N3—C4—C5	174.55 (18)	C15—N16—C17—C18	0.5 (3)
C1—N1—C5—N6	−179.24 (17)	C14—C13—C18—C17	−1.9 (3)
C12—N1—C5—N6	−2.8 (2)	C1—C13—C18—C17	178.83 (17)
C1—N1—C5—C4	−5.5 (3)	N16—C17—C18—C13	1.3 (3)
C12—N1—C5—C4	170.92 (17)	C4—N3—C19—C24	84.0 (3)
O1—C4—C5—N6	−5.5 (4)	N2—N3—C19—C24	−108.6 (2)
N3—C4—C5—N6	170.9 (2)	C4—N3—C19—C20	−94.8 (2)
O1—C4—C5—N1	−178.4 (2)	N2—N3—C19—C20	72.6 (2)
N3—C4—C5—N1	−2.0 (3)	C24—C19—C20—C21	3.0 (3)
N1—C5—N6—C7	2.3 (2)	N3—C19—C20—C21	−178.17 (19)
C4—C5—N6—C7	−170.8 (2)	C24—C19—C20—Cl1	−174.58 (16)
C5—N6—C7—C8	175.1 (2)	N3—C19—C20—Cl1	4.3 (3)
C5—N6—C7—C12	−1.0 (2)	C19—C20—C21—C22	−1.6 (3)
N6—C7—C8—C9	−175.5 (2)	Cl1—C20—C21—C22	175.98 (18)
C12—C7—C8—C9	0.2 (3)	C20—C21—C22—C23	−0.7 (4)
C7—C8—C9—C10	−0.4 (3)	C20—C21—C22—Cl2	−178.54 (18)
C8—C9—C10—C11	0.5 (3)	C21—C22—C23—C24	1.6 (4)
C9—C10—C11—C12	−0.2 (3)	Cl2—C22—C23—C24	179.36 (18)
C10—C11—C12—N1	176.0 (2)	C20—C19—C24—C23	−2.1 (3)
C10—C11—C12—C7	0.0 (3)	N3—C19—C24—C23	179.1 (2)
C5—N1—C12—C11	−174.6 (2)	C20—C19—C24—Cl3	176.14 (16)
C1—N1—C12—C11	1.2 (4)	N3—C19—C24—Cl3	−2.7 (3)
C5—N1—C12—C7	1.9 (2)	C22—C23—C24—C19	−0.1 (3)
C1—N1—C12—C7	177.75 (19)	C22—C23—C24—Cl3	−178.39 (18)
N6—C7—C12—C11	176.42 (18)