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.
Supporting information
CCDC reference: 270573
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (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
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
top
Crystal data top
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) Å3 | Block, colourless |
Z = 4 | 0.26 × 0.24 × 0.20 mm |
Data collection top
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 top
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.029 | H-atom parameters constrained |
wR(F2) = 0.087 | w = 1/[σ2(Fo2) + (0.0509P)2 + 0.0972P] where P = (Fo2 + 2Fc2)/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+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.032 (3) |
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 | 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 (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
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) top
Cl1—C1 | 1.7318 (12) | N3—C3 | 1.4604 (14) |
O1—C4i | 1.4168 (15) | N3—C3i | 1.4604 (14) |
O1—C4 | 1.4168 (15) | C2—N2i | 1.3573 (12) |
N1—C1i | 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 |
| | | |
C4i—O1—C4 | 110.91 (14) | N3—C3—C4 | 108.14 (11) |
C1i—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—C3i | 123.35 (7) | C4—C3—H3B | 110.1 |
C3—N3—C3i | 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—N2i | 118.09 (7) | C3—C4—H4B | 109.3 |
N2—C2—N2i | 123.81 (14) | H4A—C4—H4B | 107.9 |
| | | |
C2—N2—C1—N1 | 0.6 (2) | C3i—N3—C2—N2i | −2.0 (2) |
C2—N2—C1—Cl1 | −179.31 (9) | C1—N2—C2—N3 | −179.19 (13) |
C1i—N1—C1—N2 | −2.4 (2) | C1—N2—C2—N2i | 1.7 (2) |
C1i—N1—C1—Cl1 | 177.47 (7) | C2—N3—C3—C4 | −127.19 (16) |
C3—N3—C2—N2 | 2.0 (2) | C3i—N3—C3—C4 | 55.70 (17) |
C3i—N3—C2—N2 | 178.84 (12) | C4i—O1—C4—C3 | 59.08 (19) |
C3—N3—C2—N2i | −178.84 (12) | N3—C3—C4—O1 | −56.18 (15) |
Symmetry code: (i) x, −y+1/2, z. |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C3—H3B···Cl1ii | 0.97 | 2.91 | 3.736 (2) | 144 |
Symmetry code: (ii) −x+1/2, −y, z+1/2. |