2-Chloro-4,6-dimorpholino-1,3,5-triazine

The mol­ecule of the title compound, C₁₁H₁₈ClN₅O₂, possesses an approximate mirror plane and both morpholine rings adopt chair conformations.

Key indicators

• Single-crystal X-ray study
• T = 294 K
• Mean [sigma](Wave) = 0.000 Å
• R factor = 0.026
• wR factor = 0.066
• Data-to-parameter ratio = 11.7

checkCIF/PLATON results

No syntax errors found



Alert level G
REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is
            correct. If it is not, please give the correct count in the
            _publ_section_exptl_refinement section of the submitted CIF.
           From the CIF: _diffrn_reflns_theta_max           26.39
           From the CIF: _reflns_number_total               2014
           Count of symmetry unique reflns         1340
           Completeness (_total/calc)            150.30%
           TEST3: Check Friedels for noncentro structure
           Estimate of Friedel pairs measured       674
           Fraction of Friedel pairs measured     0.503
           Are heavy atom types Z>Si present        yes

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

   0 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-Chloro-4,6-di-morpholino-1,3,5-triazine

Crystal data

C11H16ClN5O2	F(000) = 600
Mr = 285.74	Dx = 1.458 Mg m^−3
Monoclinic, Cc	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: C -2yc	Cell parameters from 2215 reflections
a = 23.081 (4) Å	θ = 3.3–26.3°
b = 4.5554 (8) Å	µ = 0.30 mm^−1
c = 13.069 (2) Å	T = 294 K
β = 108.741 (2)°	Block, colourless
V = 1301.3 (4) Å^3	0.26 × 0.22 × 0.20 mm
Z = 4

Data collection

Bruker SMART CCD area-detector diffractometer	2014 independent reflections
Radiation source: fine-focus sealed tube	1903 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.014
φ and ω scans	θmax = 26.4°, θmin = 1.9°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −19→28
Tmin = 0.910, Tmax = 0.942	k = −5→5
3462 measured reflections	l = −16→14

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)] = 0.026	H-atom parameters constrained
wR(F^2) = 0.066	w = 1/[σ^2(Fo^2) + (0.0382P)^2 + 0.1478P] where P = (Fo^2 + 2Fc^2)/3
S = 1.05	(Δ/σ)max = 0.001
2014 reflections	Δρmax = 0.11 e Å^−3
172 parameters	Δρmin = −0.16 e Å^−3
2 restraints	Absolute structure: Flack (1983), 674 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.01 (5)

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	0.86849 (3)	0.63396 (10)	0.48608 (4)	0.04568 (14)
O1	0.65332 (7)	−0.0380 (3)	0.74292 (11)	0.0487 (4)
O2	1.08113 (7)	−0.1690 (3)	0.95410 (12)	0.0505 (4)
N1	0.81297 (7)	0.3363 (3)	0.59573 (12)	0.0357 (4)
N2	0.92186 (7)	0.2982 (3)	0.64848 (12)	0.0354 (3)
N3	0.86686 (7)	0.0424 (3)	0.74847 (12)	0.0338 (3)
N4	0.76241 (8)	0.0874 (3)	0.69702 (12)	0.0363 (4)
N5	0.97116 (7)	0.0071 (4)	0.79684 (12)	0.0371 (4)
C1	0.86760 (9)	0.3922 (4)	0.58995 (14)	0.0338 (4)
C2	0.91838 (8)	0.1167 (4)	0.72969 (13)	0.0314 (4)
C3	0.81545 (9)	0.1550 (4)	0.68018 (14)	0.0314 (4)
C4	0.70290 (9)	0.1256 (5)	0.61364 (16)	0.0415 (5)
H4A	0.6929	−0.0488	0.5688	0.050*
H4B	0.7047	0.2907	0.5679	0.050*
C5	0.65408 (10)	0.1791 (5)	0.66508 (18)	0.0456 (5)
H5A	0.6607	0.3701	0.6998	0.055*
H5B	0.6145	0.1828	0.6091	0.055*
C6	0.71137 (10)	−0.0467 (5)	0.82593 (17)	0.0474 (5)
H6A	0.7101	−0.1919	0.8795	0.057*
H6B	0.7196	0.1429	0.8615	0.057*
C7	0.76200 (9)	−0.1213 (4)	0.78200 (16)	0.0396 (4)
H7A	0.8009	−0.1141	0.8396	0.048*
H7B	0.7563	−0.3189	0.7528	0.048*
C8	1.02837 (9)	0.0080 (5)	0.77176 (15)	0.0434 (5)
H8A	1.0282	0.1686	0.7229	0.052*
H8B	1.0323	−0.1742	0.7362	0.052*
C9	1.08167 (10)	0.0420 (5)	0.87399 (17)	0.0484 (5)
H9A	1.1194	0.0224	0.8571	0.058*
H9B	1.0808	0.2374	0.9029	0.058*
C10	1.02603 (10)	−0.1477 (5)	0.97952 (16)	0.0442 (5)
H10A	1.0234	0.0458	1.0087	0.053*
H10B	1.0266	−0.2911	1.0347	0.053*
C11	0.97059 (9)	−0.1987 (4)	0.88248 (16)	0.0412 (4)
H11A	0.9707	−0.3988	0.8571	0.049*
H11B	0.9338	−0.1704	0.9019	0.049*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cl1	0.0513 (3)	0.0454 (2)	0.0426 (3)	0.0027 (3)	0.0183 (2)	0.0120 (2)
O1	0.0320 (7)	0.0623 (9)	0.0526 (8)	−0.0071 (7)	0.0149 (6)	0.0072 (7)
O2	0.0350 (8)	0.0647 (9)	0.0497 (8)	0.0084 (7)	0.0105 (6)	0.0126 (7)
N1	0.0328 (9)	0.0403 (8)	0.0324 (8)	0.0020 (7)	0.0084 (6)	0.0027 (6)
N2	0.0326 (8)	0.0389 (8)	0.0351 (8)	−0.0026 (7)	0.0113 (7)	0.0005 (6)
N3	0.0272 (7)	0.0386 (8)	0.0340 (7)	−0.0019 (6)	0.0077 (6)	0.0025 (7)
N4	0.0271 (8)	0.0453 (9)	0.0357 (8)	0.0003 (7)	0.0090 (6)	0.0055 (7)
N5	0.0286 (8)	0.0468 (9)	0.0363 (8)	−0.0005 (7)	0.0111 (7)	0.0087 (7)
C1	0.0419 (11)	0.0308 (8)	0.0293 (9)	−0.0019 (8)	0.0122 (8)	−0.0017 (7)
C2	0.0300 (9)	0.0346 (8)	0.0291 (8)	−0.0024 (7)	0.0089 (7)	−0.0039 (7)
C3	0.0306 (9)	0.0321 (8)	0.0308 (9)	−0.0011 (7)	0.0089 (7)	−0.0043 (7)
C4	0.0300 (10)	0.0546 (12)	0.0351 (10)	−0.0007 (9)	0.0041 (8)	0.0013 (9)
C5	0.0302 (10)	0.0532 (11)	0.0521 (12)	0.0000 (9)	0.0113 (9)	0.0055 (10)
C6	0.0376 (11)	0.0628 (12)	0.0434 (11)	−0.0079 (10)	0.0152 (9)	0.0041 (10)
C7	0.0311 (10)	0.0442 (10)	0.0419 (11)	−0.0042 (8)	0.0094 (8)	0.0052 (9)
C8	0.0313 (11)	0.0620 (12)	0.0389 (11)	0.0025 (9)	0.0141 (9)	0.0051 (10)
C9	0.0290 (11)	0.0639 (12)	0.0518 (12)	−0.0008 (10)	0.0125 (9)	0.0080 (11)
C10	0.0383 (11)	0.0531 (12)	0.0395 (10)	0.0031 (9)	0.0101 (8)	0.0053 (9)
C11	0.0346 (10)	0.0460 (10)	0.0419 (10)	−0.0018 (9)	0.0107 (8)	0.0097 (8)

Geometric parameters (Å, º)

Cl1—C1	1.7535 (18)	C4—H4B	0.9700
O1—C5	1.423 (2)	C5—H5A	0.9700
O1—C6	1.428 (3)	C5—H5B	0.9700
O2—C10	1.417 (3)	C6—C7	1.497 (3)
O2—C9	1.424 (3)	C6—H6A	0.9700
N1—C1	1.312 (3)	C6—H6B	0.9700
N1—C3	1.365 (2)	C7—H7A	0.9700
N2—C1	1.312 (2)	C7—H7B	0.9700
N2—C2	1.368 (2)	C8—C9	1.505 (3)
N3—C2	1.333 (2)	C8—H8A	0.9700
N3—C3	1.337 (2)	C8—H8B	0.9700
N4—C3	1.347 (3)	C9—H9A	0.9700
N4—C4	1.464 (2)	C9—H9B	0.9700
N4—C7	1.464 (2)	C10—C11	1.502 (3)
N5—C2	1.348 (2)	C10—H10A	0.9700
N5—C8	1.459 (3)	C10—H10B	0.9700
N5—C11	1.463 (2)	C11—H11A	0.9700
C4—C5	1.506 (3)	C11—H11B	0.9700
C4—H4A	0.9700
C5—O1—C6	109.79 (16)	C7—C6—H6A	109.2
C10—O2—C9	110.28 (15)	O1—C6—H6B	109.2
C1—N1—C3	111.87 (15)	C7—C6—H6B	109.2
C1—N2—C2	111.50 (16)	H6A—C6—H6B	107.9
C2—N3—C3	115.63 (16)	N4—C7—C6	109.86 (16)
C3—N4—C4	122.40 (16)	N4—C7—H7A	109.7
C3—N4—C7	120.00 (15)	C6—C7—H7A	109.7
C4—N4—C7	114.12 (15)	N4—C7—H7B	109.7
C2—N5—C8	123.12 (15)	C6—C7—H7B	109.7
C2—N5—C11	120.47 (16)	H7A—C7—H7B	108.2
C8—N5—C11	113.89 (15)	N5—C8—C9	109.96 (16)
N1—C1—N2	131.16 (17)	N5—C8—H8A	109.7
N1—C1—Cl1	114.65 (14)	C9—C8—H8A	109.7
N2—C1—Cl1	114.20 (15)	N5—C8—H8B	109.7
N3—C2—N5	117.33 (15)	C9—C8—H8B	109.7
N3—C2—N2	125.08 (16)	H8A—C8—H8B	108.2
N5—C2—N2	117.58 (16)	O2—C9—C8	112.68 (17)
N3—C3—N4	117.48 (16)	O2—C9—H9A	109.1
N3—C3—N1	124.72 (17)	C8—C9—H9A	109.1
N4—C3—N1	117.79 (16)	O2—C9—H9B	109.1
N4—C4—C5	110.17 (17)	C8—C9—H9B	109.1
N4—C4—H4A	109.6	H9A—C9—H9B	107.8
C5—C4—H4A	109.6	O2—C10—C11	112.13 (17)
N4—C4—H4B	109.6	O2—C10—H10A	109.2
C5—C4—H4B	109.6	C11—C10—H10A	109.2
H4A—C4—H4B	108.1	O2—C10—H10B	109.2
O1—C5—C4	112.93 (17)	C11—C10—H10B	109.2
O1—C5—H5A	109.0	H10A—C10—H10B	107.9
C4—C5—H5A	109.0	N5—C11—C10	109.39 (16)
O1—C5—H5B	109.0	N5—C11—H11A	109.8
C4—C5—H5B	109.0	C10—C11—H11A	109.8
H5A—C5—H5B	107.8	N5—C11—H11B	109.8
O1—C6—C7	111.85 (16)	C10—C11—H11B	109.8
O1—C6—H6A	109.2	H11A—C11—H11B	108.2
C3—N1—C1—N2	2.1 (3)	C1—N1—C3—N3	−1.0 (2)
C3—N1—C1—Cl1	−177.96 (11)	C1—N1—C3—N4	178.08 (16)
C2—N2—C1—N1	−1.6 (3)	C3—N4—C4—C5	−152.15 (18)
C2—N2—C1—Cl1	178.46 (11)	C7—N4—C4—C5	48.9 (2)
C3—N3—C2—N5	−179.92 (16)	C6—O1—C5—C4	58.6 (2)
C3—N3—C2—N2	0.9 (2)	N4—C4—C5—O1	−52.6 (2)
C8—N5—C2—N3	164.38 (17)	C5—O1—C6—C7	−60.3 (2)
C11—N5—C2—N3	3.5 (2)	C3—N4—C7—C6	149.67 (17)
C8—N5—C2—N2	−16.4 (3)	C4—N4—C7—C6	−50.9 (2)
C11—N5—C2—N2	−177.27 (16)	O1—C6—C7—N4	56.0 (2)
C1—N2—C2—N3	−0.1 (2)	C2—N5—C8—C9	147.41 (19)
C1—N2—C2—N5	−179.26 (16)	C11—N5—C8—C9	−50.6 (2)
C2—N3—C3—N4	−179.38 (15)	C10—O2—C9—C8	−58.1 (2)
C2—N3—C3—N1	−0.3 (2)	N5—C8—C9—O2	53.1 (2)
C4—N4—C3—N3	−162.60 (16)	C9—O2—C10—C11	59.5 (2)
C7—N4—C3—N3	−4.9 (2)	C2—N5—C11—C10	−145.56 (18)
C4—N4—C3—N1	18.3 (2)	C8—N5—C11—C10	51.9 (2)
C7—N4—C3—N1	175.99 (15)	O2—C10—C11—N5	−55.9 (2)