2,4-Dichloro-6-morpholino-1,3,5-triazine

This paper reports the synthesis of the title compound, C₇H₈Cl₂N₄O, and its crystal structure. The mol­ecule possesses a mirror plane and the morpholine ring adopts a chair conformation.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.002 Å
• R factor = 0.029
• wR factor = 0.087
• Data-to-parameter ratio = 18.0

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT199_ALERT_1_C Check the Reported cell_measurement_temperature         293
PLAT200_ALERT_1_C Check the Reported cell_ambient_temperature ....        293
PLAT480_ALERT_4_C Long H...A H-Bond Reported H3B    ..  CL1     ..       2.91 Ang.

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

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

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Computing details

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

2,4-Dichloro-6-morpholino-1,3,5-triazine

Crystal data

C7H8Cl2N4O	F(000) = 480
Mr = 235.07	Dx = 1.621 Mg m^−3
Orthorhombic, Pnma	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2n	Cell parameters from 2735 reflections
a = 9.6003 (11) Å	θ = 2.6–28.1°
b = 13.0545 (15) Å	µ = 0.65 mm^−1
c = 7.6874 (9) Å	T = 293 K
V = 963.44 (19) Å^3	Block, colourless
Z = 4	0.26 × 0.24 × 0.20 mm

Data collection

Bruker SMART 1000 CCD area-detector diffractometer	1278 independent reflections
Radiation source: fine-focus sealed tube	1056 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.017
φ and ω scans	θmax = 28.6°, θmin = 3.1°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −11→12
Tmin = 0.833, Tmax = 0.879	k = −17→14
6195 measured reflections	l = −10→9

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)] = 0.029	H-atom parameters constrained
wR(F^2) = 0.087	w = 1/[σ^2(Fo^2) + (0.0509P)^2 + 0.0972P] where P = (Fo^2 + 2Fc^2)/3
S = 1.08	(Δ/σ)max = 0.001
1278 reflections	Δρmax = 0.24 e Å^−3
71 parameters	Δρmin = −0.22 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: 0.032 (3)

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
Cl1	0.22582 (4)	0.05249 (3)	0.18408 (5)	0.05695 (17)
O1	0.55987 (15)	0.2500	0.96649 (17)	0.0608 (4)
N1	0.23900 (16)	0.2500	0.19224 (17)	0.0422 (3)
N2	0.36291 (10)	0.15828 (7)	0.41014 (12)	0.0406 (2)
N3	0.48670 (15)	0.2500	0.61450 (19)	0.0421 (3)
C1	0.28331 (12)	0.16664 (9)	0.27363 (16)	0.0390 (3)
C2	0.40358 (16)	0.2500	0.4760 (2)	0.0369 (3)
C3	0.53968 (14)	0.15660 (10)	0.69544 (16)	0.0466 (3)
H3A	0.6396	0.1518	0.6790	0.056*
H3B	0.4966	0.0970	0.6427	0.056*
C4	0.50568 (16)	0.16061 (11)	0.88686 (18)	0.0542 (4)
H4A	0.4054	0.1591	0.9018	0.065*
H4B	0.5441	0.1006	0.9438	0.065*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cl1	0.0744 (3)	0.0405 (2)	0.0560 (2)	−0.00876 (14)	−0.01340 (15)	−0.00351 (13)
O1	0.0685 (9)	0.0690 (9)	0.0449 (7)	0.000	−0.0195 (7)	0.000
N1	0.0488 (8)	0.0421 (8)	0.0355 (7)	0.000	−0.0017 (6)	0.000
N2	0.0432 (5)	0.0385 (5)	0.0400 (5)	0.0003 (4)	−0.0004 (4)	0.0002 (4)
N3	0.0472 (8)	0.0415 (7)	0.0377 (7)	0.000	−0.0037 (6)	0.000
C1	0.0418 (6)	0.0387 (6)	0.0365 (6)	−0.0026 (4)	0.0035 (4)	−0.0023 (5)
C2	0.0350 (7)	0.0404 (8)	0.0354 (7)	0.000	0.0043 (6)	0.000
C3	0.0451 (7)	0.0482 (7)	0.0465 (7)	0.0050 (5)	−0.0052 (5)	0.0027 (5)
C4	0.0561 (8)	0.0611 (8)	0.0454 (7)	−0.0018 (6)	−0.0069 (6)	0.0098 (6)

Geometric parameters (Å, º)

Cl1—C1	1.7318 (12)	N3—C3	1.4604 (14)
O1—C4^i	1.4168 (15)	N3—C3^i	1.4604 (14)
O1—C4	1.4168 (15)	C2—N2^i	1.3573 (12)
N1—C1^i	1.3254 (14)	C3—C4	1.5083 (19)
N1—C1	1.3254 (14)	C3—H3A	0.9700
N2—C1	1.3028 (15)	C3—H3B	0.9700
N2—C2	1.3573 (12)	C4—H4A	0.9700
N3—C2	1.331 (2)	C4—H4B	0.9700
C4^i—O1—C4	110.91 (14)	N3—C3—C4	108.14 (11)
C1^i—N1—C1	110.39 (14)	N3—C3—H3A	110.1
C1—N2—C2	113.28 (10)	C4—C3—H3A	110.1
C2—N3—C3	123.35 (7)	N3—C3—H3B	110.1
C2—N3—C3^i	123.35 (7)	C4—C3—H3B	110.1
C3—N3—C3^i	113.22 (14)	H3A—C3—H3B	108.4
N2—C1—N1	129.59 (11)	O1—C4—C3	111.76 (12)
N2—C1—Cl1	115.79 (9)	O1—C4—H4A	109.3
N1—C1—Cl1	114.62 (9)	C3—C4—H4A	109.3
N3—C2—N2	118.09 (7)	O1—C4—H4B	109.3
N3—C2—N2^i	118.09 (7)	C3—C4—H4B	109.3
N2—C2—N2^i	123.81 (14)	H4A—C4—H4B	107.9
C2—N2—C1—N1	0.6 (2)	C3^i—N3—C2—N2^i	−2.0 (2)
C2—N2—C1—Cl1	−179.31 (9)	C1—N2—C2—N3	−179.19 (13)
C1^i—N1—C1—N2	−2.4 (2)	C1—N2—C2—N2^i	1.7 (2)
C1^i—N1—C1—Cl1	177.47 (7)	C2—N3—C3—C4	−127.19 (16)
C3—N3—C2—N2	2.0 (2)	C3^i—N3—C3—C4	55.70 (17)
C3^i—N3—C2—N2	178.84 (12)	C4^i—O1—C4—C3	59.08 (19)
C3—N3—C2—N2^i	−178.84 (12)	N3—C3—C4—O1	−56.18 (15)

Symmetry code: (i) x, −y+1/2, z.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3B···Cl1^ii	0.97	2.91	3.736 (2)	144

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