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

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805019021/ww6398sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536805019021/ww6398Isup2.hkl
Contains datablock I

CCDC reference: 277811

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

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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

Computing details top

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 top
Crystal data top
C11H16ClN5O2F(000) = 600
Mr = 285.74Dx = 1.458 Mg m3
Monoclinic, CcMo Kα radiation, λ = 0.71073 Å
Hall symbol: C -2ycCell parameters from 2215 reflections
a = 23.081 (4) Åθ = 3.3–26.3°
b = 4.5554 (8) ŵ = 0.30 mm1
c = 13.069 (2) ÅT = 294 K
β = 108.741 (2)°Block, colourless
V = 1301.3 (4) Å30.26 × 0.22 × 0.20 mm
Z = 4
Data collection top
Bruker SMART CCD area-detector
diffractometer
2014 independent reflections
Radiation source: fine-focus sealed tube1903 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.014
φ and ω scansθmax = 26.4°, θmin = 1.9°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 1928
Tmin = 0.910, Tmax = 0.942k = 55
3462 measured reflectionsl = 1614
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.026H-atom parameters constrained
wR(F2) = 0.066 w = 1/[σ2(Fo2) + (0.0382P)2 + 0.1478P]
where P = (Fo2 + 2Fc2)/3
S = 1.05(Δ/σ)max = 0.001
2014 reflectionsΔρmax = 0.11 e Å3
172 parametersΔρmin = 0.16 e Å3
2 restraintsAbsolute structure: Flack (1983), 674 Friedel pairs
Primary atom site location: structure-invariant direct methodsAbsolute structure parameter: 0.01 (5)
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
xyzUiso*/Ueq
Cl10.86849 (3)0.63396 (10)0.48608 (4)0.04568 (14)
O10.65332 (7)0.0380 (3)0.74292 (11)0.0487 (4)
O21.08113 (7)0.1690 (3)0.95410 (12)0.0505 (4)
N10.81297 (7)0.3363 (3)0.59573 (12)0.0357 (4)
N20.92186 (7)0.2982 (3)0.64848 (12)0.0354 (3)
N30.86686 (7)0.0424 (3)0.74847 (12)0.0338 (3)
N40.76241 (8)0.0874 (3)0.69702 (12)0.0363 (4)
N50.97116 (7)0.0071 (4)0.79684 (12)0.0371 (4)
C10.86760 (9)0.3922 (4)0.58995 (14)0.0338 (4)
C20.91838 (8)0.1167 (4)0.72969 (13)0.0314 (4)
C30.81545 (9)0.1550 (4)0.68018 (14)0.0314 (4)
C40.70290 (9)0.1256 (5)0.61364 (16)0.0415 (5)
H4A0.69290.04880.56880.050*
H4B0.70470.29070.56790.050*
C50.65408 (10)0.1791 (5)0.66508 (18)0.0456 (5)
H5A0.66070.37010.69980.055*
H5B0.61450.18280.60910.055*
C60.71137 (10)0.0467 (5)0.82593 (17)0.0474 (5)
H6A0.71010.19190.87950.057*
H6B0.71960.14290.86150.057*
C70.76200 (9)0.1213 (4)0.78200 (16)0.0396 (4)
H7A0.80090.11410.83960.048*
H7B0.75630.31890.75280.048*
C81.02837 (9)0.0080 (5)0.77176 (15)0.0434 (5)
H8A1.02820.16860.72290.052*
H8B1.03230.17420.73620.052*
C91.08167 (10)0.0420 (5)0.87399 (17)0.0484 (5)
H9A1.11940.02240.85710.058*
H9B1.08080.23740.90290.058*
C101.02603 (10)0.1477 (5)0.97952 (16)0.0442 (5)
H10A1.02340.04581.00870.053*
H10B1.02660.29111.03470.053*
C110.97059 (9)0.1987 (4)0.88248 (16)0.0412 (4)
H11A0.97070.39880.85710.049*
H11B0.93380.17040.90190.049*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl10.0513 (3)0.0454 (2)0.0426 (3)0.0027 (3)0.0183 (2)0.0120 (2)
O10.0320 (7)0.0623 (9)0.0526 (8)0.0071 (7)0.0149 (6)0.0072 (7)
O20.0350 (8)0.0647 (9)0.0497 (8)0.0084 (7)0.0105 (6)0.0126 (7)
N10.0328 (9)0.0403 (8)0.0324 (8)0.0020 (7)0.0084 (6)0.0027 (6)
N20.0326 (8)0.0389 (8)0.0351 (8)0.0026 (7)0.0113 (7)0.0005 (6)
N30.0272 (7)0.0386 (8)0.0340 (7)0.0019 (6)0.0077 (6)0.0025 (7)
N40.0271 (8)0.0453 (9)0.0357 (8)0.0003 (7)0.0090 (6)0.0055 (7)
N50.0286 (8)0.0468 (9)0.0363 (8)0.0005 (7)0.0111 (7)0.0087 (7)
C10.0419 (11)0.0308 (8)0.0293 (9)0.0019 (8)0.0122 (8)0.0017 (7)
C20.0300 (9)0.0346 (8)0.0291 (8)0.0024 (7)0.0089 (7)0.0039 (7)
C30.0306 (9)0.0321 (8)0.0308 (9)0.0011 (7)0.0089 (7)0.0043 (7)
C40.0300 (10)0.0546 (12)0.0351 (10)0.0007 (9)0.0041 (8)0.0013 (9)
C50.0302 (10)0.0532 (11)0.0521 (12)0.0000 (9)0.0113 (9)0.0055 (10)
C60.0376 (11)0.0628 (12)0.0434 (11)0.0079 (10)0.0152 (9)0.0041 (10)
C70.0311 (10)0.0442 (10)0.0419 (11)0.0042 (8)0.0094 (8)0.0052 (9)
C80.0313 (11)0.0620 (12)0.0389 (11)0.0025 (9)0.0141 (9)0.0051 (10)
C90.0290 (11)0.0639 (12)0.0518 (12)0.0008 (10)0.0125 (9)0.0080 (11)
C100.0383 (11)0.0531 (12)0.0395 (10)0.0031 (9)0.0101 (8)0.0053 (9)
C110.0346 (10)0.0460 (10)0.0419 (10)0.0018 (9)0.0107 (8)0.0097 (8)
Geometric parameters (Å, º) top
Cl1—C11.7535 (18)C4—H4B0.9700
O1—C51.423 (2)C5—H5A0.9700
O1—C61.428 (3)C5—H5B0.9700
O2—C101.417 (3)C6—C71.497 (3)
O2—C91.424 (3)C6—H6A0.9700
N1—C11.312 (3)C6—H6B0.9700
N1—C31.365 (2)C7—H7A0.9700
N2—C11.312 (2)C7—H7B0.9700
N2—C21.368 (2)C8—C91.505 (3)
N3—C21.333 (2)C8—H8A0.9700
N3—C31.337 (2)C8—H8B0.9700
N4—C31.347 (3)C9—H9A0.9700
N4—C41.464 (2)C9—H9B0.9700
N4—C71.464 (2)C10—C111.502 (3)
N5—C21.348 (2)C10—H10A0.9700
N5—C81.459 (3)C10—H10B0.9700
N5—C111.463 (2)C11—H11A0.9700
C4—C51.506 (3)C11—H11B0.9700
C4—H4A0.9700
C5—O1—C6109.79 (16)C7—C6—H6A109.2
C10—O2—C9110.28 (15)O1—C6—H6B109.2
C1—N1—C3111.87 (15)C7—C6—H6B109.2
C1—N2—C2111.50 (16)H6A—C6—H6B107.9
C2—N3—C3115.63 (16)N4—C7—C6109.86 (16)
C3—N4—C4122.40 (16)N4—C7—H7A109.7
C3—N4—C7120.00 (15)C6—C7—H7A109.7
C4—N4—C7114.12 (15)N4—C7—H7B109.7
C2—N5—C8123.12 (15)C6—C7—H7B109.7
C2—N5—C11120.47 (16)H7A—C7—H7B108.2
C8—N5—C11113.89 (15)N5—C8—C9109.96 (16)
N1—C1—N2131.16 (17)N5—C8—H8A109.7
N1—C1—Cl1114.65 (14)C9—C8—H8A109.7
N2—C1—Cl1114.20 (15)N5—C8—H8B109.7
N3—C2—N5117.33 (15)C9—C8—H8B109.7
N3—C2—N2125.08 (16)H8A—C8—H8B108.2
N5—C2—N2117.58 (16)O2—C9—C8112.68 (17)
N3—C3—N4117.48 (16)O2—C9—H9A109.1
N3—C3—N1124.72 (17)C8—C9—H9A109.1
N4—C3—N1117.79 (16)O2—C9—H9B109.1
N4—C4—C5110.17 (17)C8—C9—H9B109.1
N4—C4—H4A109.6H9A—C9—H9B107.8
C5—C4—H4A109.6O2—C10—C11112.13 (17)
N4—C4—H4B109.6O2—C10—H10A109.2
C5—C4—H4B109.6C11—C10—H10A109.2
H4A—C4—H4B108.1O2—C10—H10B109.2
O1—C5—C4112.93 (17)C11—C10—H10B109.2
O1—C5—H5A109.0H10A—C10—H10B107.9
C4—C5—H5A109.0N5—C11—C10109.39 (16)
O1—C5—H5B109.0N5—C11—H11A109.8
C4—C5—H5B109.0C10—C11—H11A109.8
H5A—C5—H5B107.8N5—C11—H11B109.8
O1—C6—C7111.85 (16)C10—C11—H11B109.8
O1—C6—H6A109.2H11A—C11—H11B108.2
C3—N1—C1—N22.1 (3)C1—N1—C3—N31.0 (2)
C3—N1—C1—Cl1177.96 (11)C1—N1—C3—N4178.08 (16)
C2—N2—C1—N11.6 (3)C3—N4—C4—C5152.15 (18)
C2—N2—C1—Cl1178.46 (11)C7—N4—C4—C548.9 (2)
C3—N3—C2—N5179.92 (16)C6—O1—C5—C458.6 (2)
C3—N3—C2—N20.9 (2)N4—C4—C5—O152.6 (2)
C8—N5—C2—N3164.38 (17)C5—O1—C6—C760.3 (2)
C11—N5—C2—N33.5 (2)C3—N4—C7—C6149.67 (17)
C8—N5—C2—N216.4 (3)C4—N4—C7—C650.9 (2)
C11—N5—C2—N2177.27 (16)O1—C6—C7—N456.0 (2)
C1—N2—C2—N30.1 (2)C2—N5—C8—C9147.41 (19)
C1—N2—C2—N5179.26 (16)C11—N5—C8—C950.6 (2)
C2—N3—C3—N4179.38 (15)C10—O2—C9—C858.1 (2)
C2—N3—C3—N10.3 (2)N5—C8—C9—O253.1 (2)
C4—N4—C3—N3162.60 (16)C9—O2—C10—C1159.5 (2)
C7—N4—C3—N34.9 (2)C2—N5—C11—C10145.56 (18)
C4—N4—C3—N118.3 (2)C8—N5—C11—C1051.9 (2)
C7—N4—C3—N1175.99 (15)O2—C10—C11—N555.9 (2)
 

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