{3-[(4-Chloro­anilino)­carbonyl]-2-[(3,4-di­chloro­phenyl)­imino]-8-methyl-2H-pyrano­[2,3-c]­pyridin-5-yl}methyl acetate

The coplanar arrangement of rings in the title mol­ecule, C₂₅H₁₈Cl₃N₃O₄, is accompanied by the formation of short intramolecular O...H (2.20 and 2.26 Å) contacts. A strong N—H...N hydrogen bond [N...N = 2.698 (4) Å and N—H...N = 142°] is present and, as a result, the exocyclic bond angles at the C atoms in the 2- and 3-positions of the pyran­one ring are slightly distorted. The coplanar rings form a layered structure in which a short intermolecular Cl...Cl(−x, 1 − y, 1 − z) contact of 3.280 (2) Å is observed.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.043
• wR factor = 0.071
• Data-to-parameter ratio = 13.0

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT230_ALERT_2_B Hirshfeld Test Diff for    Cl1    -   C12      =      13.55 su
PLAT230_ALERT_2_B Hirshfeld Test Diff for    O1     -   C2       =      11.35 su
PLAT230_ALERT_2_B Hirshfeld Test Diff for    O3     -   C23      =       9.08 su
PLAT230_ALERT_2_B Hirshfeld Test Diff for    O4     -   C24      =       7.83 su
PLAT230_ALERT_2_B Hirshfeld Test Diff for    N7     -   C6       =       7.77 su
PLAT230_ALERT_2_B Hirshfeld Test Diff for    C3     -   C16      =      16.38 su
PLAT230_ALERT_2_B Hirshfeld Test Diff for    C5     -   C6       =      11.54 su
PLAT230_ALERT_2_B Hirshfeld Test Diff for    C13    -   C14      =      10.62 su
PLAT230_ALERT_2_B Hirshfeld Test Diff for    C17    -   C18      =       8.68 su
PLAT230_ALERT_2_B Hirshfeld Test Diff for    C17    -   C22      =      10.68 su
PLAT230_ALERT_2_B Hirshfeld Test Diff for    C18    -   C19      =      10.32 su
PLAT230_ALERT_2_B Hirshfeld Test Diff for    C19    -   C20      =      11.88 su
PLAT230_ALERT_2_B Hirshfeld Test Diff for    C20    -   C21      =       9.83 su

Alert level C
PLAT026_ALERT_3_C Ratio Observed / Unique Reflections too Low ....         42 Perc.
PLAT230_ALERT_2_C Hirshfeld Test Diff for    O2     -   C16      =       5.32 su
PLAT230_ALERT_2_C Hirshfeld Test Diff for    C3     -   C4       =       6.76 su
PLAT230_ALERT_2_C Hirshfeld Test Diff for    C24    -   C25      =       6.67 su
PLAT242_ALERT_2_C Check Low    U(eq) as Compared to Neighbors ....        C24
PLAT250_ALERT_2_C Large U3/U1 ratio for average U(i,j) tensor ....       2.30
PLAT369_ALERT_2_C Long   C(sp2)-C(sp2) Bond  C3     -   C16      =       1.54 Ang.
PLAT431_ALERT_2_C Short Inter HL..A Contact  Cl1    ..  Cl1      =       3.28 Ang.

   0 ALERT level A = In general: serious problem
  13 ALERT level B = Potentially serious problem
   8 ALERT level C = Check and explain
   0 ALERT level G = General alerts; check

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

---

Computing details

Data collection: P3 (Siemens, 1989); cell refinement: P3; data reduction: XDISK, XPREP (Siemens, 1991); program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: XP (Siemens, 1991); software used to prepare material for publication: WinGX (Farrugia, 1999).

(I)

Crystal data

C25H18Cl3N3O4	Z = 2
Mr = 530.77	F(000) = 544
Triclinic, P1	Dx = 1.501 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 9.020 (2) Å	Cell parameters from 24 reflections
b = 11.390 (3) Å	θ = 20–22°
c = 12.890 (3) Å	µ = 0.43 mm^−1
α = 73.95 (2)°	T = 293 K
β = 86.18 (2)°	Polyhedron, yellow
γ = 67.49 (2)°	0.25 × 0.2 × 0.2 mm
V = 1174.5 (5) Å^3

Data collection

Siemens P3/PC diffractometer	θmax = 25.0°, θmin = 2.5°
2θ/ω scans	h = −9→10
4323 measured reflections	k = 0→13
4106 independent reflections	l = −14→15
1737 reflections with I > 2σ(I)	2 standard reflections every 98 reflections
Rint = 0.077	intensity decay: 1%

Refinement

Refinement on F^2	H-atom parameters constrained
Least-squares matrix: full	w = exp(2.00(sinθ/λ)^2)/σ^2(Fo^2)
R[F^2 > 2σ(F^2)] = 0.043	(Δ/σ)max = 0.01
wR(F^2) = 0.071	Δρmax = 0.19 e Å^−3
S = 0.92	Δρmin = −0.15 e Å^−3
4106 reflections	Extinction correction: SHELXL97, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
317 parameters	Extinction coefficient: 0.0060 (5)
0 restraints

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.

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

	x	y	z	Uiso*/Ueq
Cl1	0.11722 (7)	0.51062 (7)	0.39792 (5)	0.0935 (2)
Cl2	0.25202 (7)	0.50208 (6)	0.16860 (5)	0.07838 (18)
Cl3	1.18957 (7)	0.98670 (7)	0.12625 (5)	0.0818 (2)
O1	0.35305 (13)	0.72038 (12)	0.58927 (9)	0.0510 (4)
C2	0.4710 (2)	0.75370 (18)	0.53230 (15)	0.0427 (5)
C3	0.5543 (2)	0.81505 (19)	0.58056 (15)	0.0475 (6)
C4	0.52092 (19)	0.82912 (19)	0.68041 (14)	0.0453 (5)
H4	0.5769	0.8657	0.7112	0.054*
C4A	0.4016 (2)	0.78914 (19)	0.74052 (14)	0.0444 (6)
C5	0.3622 (2)	0.7954 (2)	0.84744 (15)	0.0530 (6)
C6	0.2424 (2)	0.7503 (2)	0.89325 (16)	0.0646 (6)
H6	0.2133	0.7565	0.9627	0.078*
N7	0.16775 (18)	0.69951 (18)	0.84422 (14)	0.0658 (6)
C8	0.1994 (2)	0.6940 (2)	0.74420 (16)	0.0557 (6)
C8A	0.3207 (2)	0.73430 (19)	0.69206 (15)	0.0441 (6)
N1	0.50580 (16)	0.73224 (15)	0.43971 (12)	0.0507 (5)
C10	0.4365 (2)	0.67431 (19)	0.38233 (15)	0.0495 (6)
C11	0.3193 (2)	0.62361 (19)	0.41863 (16)	0.0511 (6)
H11	0.2793	0.6253	0.4868	0.061*
C12	0.2611 (2)	0.5702 (2)	0.35315 (16)	0.0542 (6)
C13	0.3219 (2)	0.5657 (2)	0.25138 (16)	0.0577 (6)
C14	0.4424 (2)	0.6138 (2)	0.21785 (16)	0.0641 (6)
H14	0.4855	0.6103	0.1507	0.077*
C15	0.4989 (2)	0.6666 (2)	0.28337 (15)	0.0559 (6)
H15	0.5805	0.6974	0.2601	0.067*
C16	0.6852 (2)	0.86291 (19)	0.52368 (14)	0.0480 (5)
O2	0.73725 (15)	0.92131 (14)	0.56770 (11)	0.0719 (4)
N2	0.72985 (17)	0.83695 (16)	0.43170 (12)	0.0542 (5)
H2	0.6864	0.7937	0.4105	0.065*
C17	0.8441 (2)	0.87390 (19)	0.36290 (14)	0.0517 (6)
C18	0.9441 (2)	0.9266 (2)	0.39163 (16)	0.0534 (6)
H18	0.94	0.9396	0.46	0.064*
C19	1.0510 (2)	0.9603 (2)	0.31876 (16)	0.0632 (7)
H19	1.118	0.9964	0.3381	0.076*
C20	1.0577 (2)	0.9406 (2)	0.21916 (17)	0.0640 (7)
C21	0.9621 (2)	0.8859 (2)	0.19042 (16)	0.0630 (7)
H21	0.9684	0.8724	0.122	0.076*
C22	0.8584 (2)	0.8508 (2)	0.26031 (16)	0.0515 (6)
H22	0.7959	0.8113	0.2404	0.062*
C23	0.4480 (2)	0.8470 (2)	0.91081 (16)	0.0615 (6)
H23A	0.4447	0.9332	0.8695	0.074*
H23B	0.396	0.8551	0.9783	0.074*
O3	0.60924 (14)	0.75544 (13)	0.93177 (11)	0.0599 (4)
C24	0.6894 (2)	0.7581 (2)	1.01209 (15)	0.0487 (6)
O4	0.63530 (16)	0.83786 (15)	1.06191 (11)	0.0751 (5)
C25	0.8529 (2)	0.6556 (2)	1.0276 (2)	0.0794 (8)
H25A	0.9054	0.6563	1.0897	0.095*
H25B	0.9124	0.6735	0.9647	0.095*
H25C	0.8477	0.5704	1.0384	0.095*
C26	0.1048 (2)	0.6442 (2)	0.68991 (18)	0.0750 (7)
H26A	0.1766	0.5709	0.6652	0.09*
H26B	0.0431	0.7133	0.6293	0.09*
H26C	0.0337	0.6159	0.7402	0.09*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cl1	0.0945 (3)	0.1211 (4)	0.1039 (5)	−0.0728 (3)	0.0094 (3)	−0.0459 (4)
Cl2	0.0937 (3)	0.0921 (3)	0.0705 (3)	−0.0421 (3)	−0.0229 (3)	−0.0388 (3)
Cl3	0.0922 (4)	0.1021 (4)	0.0694 (4)	−0.0580 (3)	0.0342 (3)	−0.0284 (3)
O1	0.0576 (6)	0.0796 (8)	0.0392 (7)	−0.0471 (6)	0.0060 (6)	−0.0228 (6)
C2	0.0429 (9)	0.0495 (11)	0.0430 (10)	−0.0179 (9)	−0.0024 (9)	−0.0226 (9)
C3	0.0561 (11)	0.0442 (11)	0.0437 (11)	−0.0198 (9)	−0.0171 (9)	−0.0086 (9)
C4	0.0369 (9)	0.0660 (11)	0.0467 (11)	−0.0256 (9)	−0.0027 (8)	−0.0265 (9)
C4A	0.0408 (10)	0.0539 (11)	0.0436 (11)	−0.0149 (9)	0.0017 (9)	−0.0257 (9)
C5	0.0469 (11)	0.0686 (13)	0.0441 (11)	−0.0143 (10)	−0.0072 (9)	−0.0253 (10)
C6	0.0725 (12)	0.1051 (14)	0.0424 (11)	−0.0538 (11)	0.0180 (10)	−0.0350 (10)
N7	0.0617 (10)	0.0930 (13)	0.0574 (11)	−0.0435 (9)	0.0162 (9)	−0.0260 (10)
C8	0.0543 (11)	0.0676 (14)	0.0505 (12)	−0.0299 (10)	−0.0003 (10)	−0.0142 (11)
C8A	0.0417 (10)	0.0560 (12)	0.0372 (10)	−0.0204 (9)	−0.0022 (9)	−0.0129 (9)
N1	0.0641 (8)	0.0690 (9)	0.0436 (9)	−0.0445 (8)	−0.0005 (7)	−0.0249 (8)
C10	0.0505 (10)	0.0678 (12)	0.0469 (11)	−0.0312 (9)	−0.0022 (9)	−0.0276 (9)
C11	0.0550 (10)	0.0658 (12)	0.0487 (11)	−0.0369 (9)	−0.0031 (9)	−0.0194 (9)
C12	0.0520 (10)	0.0653 (12)	0.0574 (13)	−0.0329 (10)	−0.0064 (10)	−0.0182 (10)
C13	0.0722 (12)	0.0545 (12)	0.0532 (12)	−0.0247 (10)	−0.0192 (10)	−0.0192 (10)
C14	0.0809 (12)	0.0899 (14)	0.0425 (11)	−0.0525 (11)	−0.0010 (10)	−0.0209 (10)
C15	0.0561 (10)	0.0857 (13)	0.0515 (12)	−0.0450 (10)	0.0080 (10)	−0.0335 (10)
C16	0.0635 (10)	0.0700 (11)	0.0352 (10)	−0.0495 (9)	−0.0021 (9)	−0.0166 (9)
O2	0.0818 (7)	0.1204 (9)	0.0585 (8)	−0.0713 (7)	0.0108 (7)	−0.0485 (7)
N2	0.0739 (9)	0.0764 (10)	0.0357 (9)	−0.0501 (8)	0.0061 (8)	−0.0214 (8)
C17	0.0726 (11)	0.0745 (12)	0.0299 (10)	−0.0485 (10)	−0.0038 (9)	−0.0168 (9)
C18	0.0535 (10)	0.0767 (13)	0.0411 (11)	−0.0339 (10)	0.0032 (9)	−0.0203 (10)
C19	0.0681 (12)	0.0864 (14)	0.0543 (13)	−0.0443 (11)	−0.0033 (11)	−0.0256 (11)
C20	0.0616 (10)	0.0868 (14)	0.0615 (14)	−0.0534 (10)	−0.0001 (10)	−0.0110 (11)
C21	0.0831 (13)	0.0941 (14)	0.0329 (11)	−0.0525 (12)	0.0130 (10)	−0.0251 (10)
C22	0.0519 (10)	0.0655 (12)	0.0534 (12)	−0.0346 (9)	0.0049 (10)	−0.0243 (10)
C23	0.0578 (12)	0.0850 (14)	0.0531 (11)	−0.0201 (11)	−0.0048 (10)	−0.0451 (10)
O3	0.0433 (7)	0.0804 (9)	0.0652 (8)	−0.0133 (7)	−0.0033 (6)	−0.0471 (7)
C24	0.0424 (10)	0.0750 (13)	0.0399 (10)	−0.0275 (10)	0.0020 (9)	−0.0257 (10)
O4	0.0856 (9)	0.1098 (10)	0.0544 (8)	−0.0469 (8)	0.0014 (7)	−0.0458 (7)
C25	0.0538 (13)	0.1005 (17)	0.0910 (17)	−0.0300 (13)	−0.0003 (12)	−0.0356 (14)
C26	0.0711 (11)	0.1157 (15)	0.0732 (15)	−0.0689 (11)	0.0103 (11)	−0.0331 (12)

Geometric parameters (Å, º)

Cl1—C12	1.684 (2)	C14—H14	0.9299
Cl2—C13	1.711 (2)	C15—H15	0.93
Cl3—C20	1.751 (2)	C16—O2	1.212 (2)
O1—C2	1.366 (2)	C16—N2	1.302 (2)
O1—C8A	1.376 (2)	N2—C17	1.425 (2)
C2—N1	1.279 (2)	N2—H2	0.8412
C2—C3	1.464 (3)	C17—C18	1.375 (3)
C3—C4	1.341 (3)	C17—C22	1.406 (3)
C3—C16	1.545 (3)	C18—C19	1.387 (3)
C4—C4A	1.427 (3)	C18—H18	0.93
C4—H4	0.93	C19—C20	1.356 (3)
C4A—C8A	1.392 (3)	C19—H19	0.93
C4A—C5	1.414 (3)	C20—C21	1.361 (3)
C5—C6	1.397 (3)	C21—C22	1.350 (3)
C5—C23	1.519 (3)	C21—H21	0.9299
C6—N7	1.321 (3)	C22—H22	0.9301
C6—H6	0.93	C23—O3	1.418 (2)
N7—C8	1.315 (3)	C23—H23A	0.97
C8—C8A	1.406 (3)	C23—H23B	0.97
C8—C26	1.487 (3)	O3—C24	1.315 (2)
N1—C10	1.421 (2)	C24—O4	1.191 (2)
C10—C15	1.371 (3)	C24—C25	1.473 (3)
C10—C11	1.386 (3)	C25—H25A	0.9599
C11—C12	1.395 (3)	C25—H25B	0.96
C11—H11	0.9301	C25—H25C	0.96
C12—C13	1.394 (3)	C26—H26A	0.9599
C13—C14	1.390 (3)	C26—H26B	0.96
C14—C15	1.381 (3)	C26—H26C	0.9599
C2—O1—C8A	121.61 (15)	O2—C16—C3	117.77 (17)
N1—C2—O1	120.56 (17)	N2—C16—C3	116.67 (17)
N1—C2—C3	121.67 (18)	C16—N2—C17	127.15 (18)
O1—C2—C3	117.78 (16)	C16—N2—H2	116.4
C4—C3—C2	119.94 (18)	C17—N2—H2	116.4
C4—C3—C16	116.52 (18)	C18—C17—C22	118.21 (18)
C2—C3—C16	123.52 (17)	C18—C17—N2	124.27 (17)
C3—C4—C4A	121.48 (19)	C22—C17—N2	117.49 (17)
C3—C4—H4	119.2	C17—C18—C19	120.13 (19)
C4A—C4—H4	119.3	C17—C18—H18	120
C8A—C4A—C5	116.69 (18)	C19—C18—H18	119.9
C8A—C4A—C4	117.66 (17)	C20—C19—C18	120.0 (2)
C5—C4A—C4	125.60 (19)	C20—C19—H19	120
C6—C5—C4A	117.2 (2)	C18—C19—H19	120
C6—C5—C23	121.17 (18)	C19—C20—C21	120.6 (2)
C4A—C5—C23	121.60 (19)	C19—C20—Cl3	119.91 (17)
N7—C6—C5	124.2 (2)	C21—C20—Cl3	119.52 (17)
N7—C6—H6	117.9	C22—C21—C20	120.6 (2)
C5—C6—H6	117.9	C22—C21—H21	119.7
C8—N7—C6	120.23 (19)	C20—C21—H21	119.7
N7—C8—C8A	119.7 (2)	C21—C22—C17	120.5 (2)
N7—C8—C26	118.31 (19)	C21—C22—H22	119.7
C8A—C8—C26	122.01 (19)	C17—C22—H22	119.8
O1—C8A—C4A	121.37 (17)	O3—C23—C5	107.66 (16)
O1—C8A—C8	116.83 (18)	O3—C23—H23A	110.3
C4A—C8A—C8	121.78 (19)	C5—C23—H23A	110.3
C2—N1—C10	128.40 (17)	O3—C23—H23B	110.1
C15—C10—C11	119.32 (19)	C5—C23—H23B	110.1
C15—C10—N1	114.36 (18)	H23A—C23—H23B	108.5
C11—C10—N1	126.29 (18)	C24—O3—C23	116.97 (15)
C10—C11—C12	120.21 (19)	O4—C24—O3	122.77 (16)
C10—C11—H11	119.9	O4—C24—C25	125.64 (19)
C12—C11—H11	119.9	O3—C24—C25	111.54 (18)
C11—C12—C13	120.26 (19)	C24—C25—H25A	109.4
C11—C12—Cl1	119.59 (16)	C24—C25—H25B	109.3
C13—C12—Cl1	120.15 (17)	H25A—C25—H25B	109.5
C14—C13—C12	118.55 (19)	C24—C25—H25C	109.8
C14—C13—Cl2	120.00 (17)	H25A—C25—H25C	109.5
C12—C13—Cl2	121.45 (17)	H25B—C25—H25C	109.5
C15—C14—C13	120.6 (2)	C8—C26—H26A	109.4
C15—C14—H14	119.7	C8—C26—H26B	109.6
C13—C14—H14	119.7	H26A—C26—H26B	109.5
C10—C15—C14	121.0 (2)	C8—C26—H26C	109.4
C10—C15—H15	119.5	H26A—C26—H26C	109.5
C14—C15—H15	119.5	H26B—C26—H26C	109.5
O2—C16—N2	125.55 (19)
C8A—O1—C2—N1	175.58 (15)	C10—C11—C12—C13	0.9 (3)
C8A—O1—C2—C3	−4.8 (2)	C10—C11—C12—Cl1	−179.29 (14)
N1—C2—C3—C4	−176.20 (17)	C11—C12—C13—C14	0.9 (3)
O1—C2—C3—C4	4.2 (2)	Cl1—C12—C13—C14	−178.97 (15)
N1—C2—C3—C16	2.1 (3)	C11—C12—C13—Cl2	−179.44 (14)
O1—C2—C3—C16	−177.48 (15)	Cl1—C12—C13—Cl2	0.7 (2)
C2—C3—C4—C4A	−1.9 (3)	C12—C13—C14—C15	−0.9 (3)
C16—C3—C4—C4A	179.63 (15)	Cl2—C13—C14—C15	179.34 (15)
C3—C4—C4A—C8A	0.2 (3)	C11—C10—C15—C14	2.5 (3)
C3—C4—C4A—C5	177.49 (18)	N1—C10—C15—C14	−179.39 (17)
C8A—C4A—C5—C6	−2.1 (3)	C13—C14—C15—C10	−0.7 (3)
C4—C4A—C5—C6	−179.42 (17)	C4—C3—C16—O2	−7.2 (2)
C8A—C4A—C5—C23	177.00 (17)	C2—C3—C16—O2	174.48 (16)
C4—C4A—C5—C23	−0.3 (3)	C4—C3—C16—N2	173.03 (16)
C4A—C5—C6—N7	1.9 (3)	C2—C3—C16—N2	−5.3 (2)
C23—C5—C6—N7	−177.21 (18)	O2—C16—N2—C17	−1.8 (3)
C5—C6—N7—C8	−3.0 (3)	C3—C16—N2—C17	178.01 (15)
C6—N7—C8—C8A	4.3 (3)	C16—N2—C17—C18	10.5 (3)
C6—N7—C8—C26	−176.06 (18)	C16—N2—C17—C22	−171.66 (17)
C2—O1—C8A—C4A	3.2 (2)	C22—C17—C18—C19	2.5 (3)
C2—O1—C8A—C8	−178.53 (16)	N2—C17—C18—C19	−179.62 (18)
C5—C4A—C8A—O1	−178.29 (16)	C17—C18—C19—C20	−0.4 (3)
C4—C4A—C8A—O1	−0.8 (2)	C18—C19—C20—C21	−1.1 (3)
C5—C4A—C8A—C8	3.6 (3)	C18—C19—C20—Cl3	178.58 (15)
C4—C4A—C8A—C8	−178.91 (17)	C19—C20—C21—C22	0.4 (3)
N7—C8—C8A—O1	177.06 (16)	Cl3—C20—C21—C22	−179.32 (16)
C26—C8—C8A—O1	−2.6 (3)	C20—C21—C22—C17	1.9 (3)
N7—C8—C8A—C4A	−4.7 (3)	C18—C17—C22—C21	−3.3 (3)
C26—C8—C8A—C4A	175.63 (17)	N2—C17—C22—C21	178.72 (17)
O1—C2—N1—C10	−0.3 (3)	C6—C5—C23—O3	111.5 (2)
C3—C2—N1—C10	−179.89 (16)	C4A—C5—C23—O3	−67.6 (2)
C2—N1—C10—C15	179.09 (17)	C5—C23—O3—C24	−159.29 (17)
C2—N1—C10—C11	−2.9 (3)	C23—O3—C24—O4	−4.5 (3)
C15—C10—C11—C12	−2.5 (3)	C23—O3—C24—C25	178.07 (18)
N1—C10—C11—C12	179.57 (17)