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The mol­ecule of the title compound, C11H19N5O4, contains three fused rings, namely two nearly planar imidazole rings and one non-planar triazine ring. The latter ring displays a chair conformation. Two hydroxy­lmethyl­ene groups are linked to two N atoms from separate rings of the glycoluril system.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806054882/at2193sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806054882/at2193Isup2.hkl
Contains datablock I

CCDC reference: 633599

Key indicators

  • Single-crystal X-ray study
  • T = 292 K
  • Mean [sigma](C-C) = 0.003 Å
  • R factor = 0.058
  • wR factor = 0.127
  • Data-to-parameter ratio = 17.0

checkCIF/PLATON results

No syntax errors found



Alert level C RINTA01_ALERT_3_C The value of Rint is greater than 0.10 Rint given 0.143 PLAT020_ALERT_3_C The value of Rint is greater than 0.10 ......... 0.14 PLAT026_ALERT_3_C Ratio Observed / Unique Reflections too Low .... 45 Perc.
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 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 3 ALERT type 3 Indicator that the structure quality may be low 0 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check

Computing details top

Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: PLATON.

2,3-Bis(hydroxymethyl)-6-(isopropyl)perhydro-2,3,4a,6,7a- pentaazacyclopenta[cd]indene-1,4-dione top
Crystal data top
C11H19N5O4F(000) = 1216
Mr = 285.31Dx = 1.472 Mg m3
Orthorhombic, PbcaMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2abCell parameters from 1672 reflections
a = 12.778 (3) Åθ = 2.6–18.7°
b = 12.655 (3) ŵ = 0.11 mm1
c = 15.926 (4) ÅT = 292 K
V = 2575.2 (11) Å3Block, colourless
Z = 80.30 × 0.20 × 0.04 mm
Data collection top
Bruker SMART 4K CCD area-detector
diffractometer
1428 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.143
Graphite monochromatorθmax = 28.3°, θmin = 2.6°
φ and ω scansh = 1616
28542 measured reflectionsk = 1616
3154 independent reflectionsl = 2120
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.058Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.127H-atom parameters constrained
S = 0.83 w = 1/[σ2(Fo2) + (0.0506P)2]
where P = (Fo2 + 2Fc2)/3
3154 reflections(Δ/σ)max < 0.001
185 parametersΔρmax = 0.18 e Å3
0 restraintsΔρmin = 0.23 e Å3
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
C11.01645 (19)0.5807 (2)0.09324 (18)0.0547 (7)
H1A0.94470.56540.08010.082*
H1B1.05400.59580.04240.082*
H1C1.01960.64090.12990.082*
C21.18386 (19)0.4952 (2)0.13349 (16)0.0575 (8)
H2A1.20550.55480.16650.086*
H2B1.20560.50500.07630.086*
H2C1.21530.43210.15550.086*
C31.06598 (18)0.48508 (17)0.13691 (14)0.0386 (6)
H31.04520.42090.10680.046*
C40.91856 (19)0.48531 (18)0.23833 (15)0.0465 (7)
H4A0.89340.54790.20960.056*
H4B0.90480.49430.29780.056*
C51.06524 (18)0.37926 (19)0.26598 (14)0.0438 (6)
H5A1.05480.38590.32610.053*
H5B1.13970.37050.25620.053*
C60.80517 (17)0.3876 (2)0.13475 (15)0.0391 (6)
C71.0459 (2)0.22792 (18)0.16873 (15)0.0377 (6)
C80.89722 (17)0.29062 (17)0.23534 (14)0.0395 (6)
H80.86680.27030.28950.047*
C90.86278 (18)0.21564 (17)0.16448 (14)0.0404 (6)
H90.82430.15440.18610.048*
C100.7275 (2)0.2451 (2)0.04964 (17)0.0577 (7)
H10A0.70200.17540.06490.069*
H10B0.66770.29200.04530.069*
C110.9724 (2)0.1086 (2)0.06053 (16)0.0524 (7)
H11A1.03600.06820.06910.063*
H11B0.91390.05990.06320.063*
N11.03086 (14)0.47639 (15)0.22556 (11)0.0401 (5)
N20.86041 (14)0.39350 (14)0.20796 (11)0.0377 (5)
N31.01064 (14)0.28447 (15)0.23645 (12)0.0371 (5)
N40.79719 (14)0.28289 (15)0.11317 (12)0.0424 (5)
N50.96231 (15)0.18518 (15)0.12720 (12)0.0401 (5)
O10.76617 (12)0.46158 (14)0.09727 (11)0.0533 (5)
O21.13844 (12)0.21494 (12)0.15089 (10)0.0511 (5)
O30.77955 (14)0.23978 (17)0.02884 (11)0.0691 (6)
H3A0.73940.25820.06620.104*
O40.97538 (14)0.15480 (16)0.01967 (11)0.0632 (6)
H40.91860.18210.03000.095*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0611 (18)0.0427 (16)0.0602 (18)0.0031 (13)0.0037 (14)0.0034 (14)
C20.0500 (17)0.0661 (19)0.0563 (18)0.0033 (13)0.0028 (14)0.0091 (14)
C30.0443 (15)0.0331 (14)0.0383 (14)0.0037 (11)0.0044 (11)0.0035 (11)
C40.0463 (16)0.0479 (16)0.0453 (15)0.0013 (12)0.0020 (12)0.0129 (13)
C50.0397 (14)0.0606 (18)0.0310 (13)0.0024 (13)0.0060 (11)0.0011 (13)
C60.0287 (13)0.0457 (16)0.0428 (15)0.0041 (12)0.0034 (11)0.0017 (13)
C70.0394 (15)0.0336 (14)0.0400 (14)0.0067 (12)0.0021 (12)0.0156 (11)
C80.0380 (15)0.0498 (16)0.0308 (13)0.0024 (11)0.0071 (11)0.0059 (11)
C90.0415 (15)0.0376 (14)0.0420 (14)0.0073 (12)0.0030 (12)0.0065 (11)
C100.0453 (16)0.0734 (19)0.0544 (17)0.0136 (15)0.0086 (14)0.0019 (15)
C110.0693 (19)0.0389 (16)0.0490 (18)0.0066 (13)0.0047 (14)0.0004 (13)
N10.0392 (12)0.0460 (13)0.0352 (12)0.0015 (9)0.0020 (9)0.0055 (10)
N20.0348 (11)0.0412 (12)0.0370 (11)0.0005 (9)0.0004 (9)0.0058 (10)
N30.0332 (12)0.0454 (13)0.0326 (11)0.0004 (9)0.0008 (9)0.0041 (9)
N40.0406 (12)0.0434 (13)0.0433 (13)0.0032 (9)0.0077 (10)0.0006 (10)
N50.0447 (12)0.0339 (11)0.0417 (12)0.0036 (9)0.0046 (10)0.0028 (9)
O10.0444 (11)0.0530 (12)0.0626 (12)0.0098 (9)0.0039 (9)0.0095 (9)
O20.0397 (11)0.0570 (12)0.0566 (11)0.0124 (8)0.0088 (9)0.0093 (9)
O30.0635 (13)0.0949 (16)0.0491 (12)0.0082 (12)0.0133 (10)0.0082 (11)
O40.0722 (14)0.0724 (15)0.0449 (11)0.0144 (11)0.0073 (10)0.0035 (10)
Geometric parameters (Å, º) top
C1—C31.533 (3)C7—O21.228 (2)
C1—H1A0.9600C7—N51.367 (3)
C1—H1B0.9600C7—N31.370 (3)
C1—H1C0.9600C8—N21.451 (3)
C2—C31.513 (3)C8—N31.452 (3)
C2—H2A0.9600C8—C91.539 (3)
C2—H2B0.9600C8—H80.9800
C2—H2C0.9600C9—N41.447 (3)
C3—N11.486 (3)C9—N51.455 (3)
C3—H30.9800C9—H90.9800
C4—N11.454 (3)C10—O31.418 (3)
C4—N21.461 (3)C10—N41.431 (3)
C4—H4A0.9700C10—H10A0.9700
C4—H4B0.9700C10—H10B0.9700
C5—N11.455 (3)C11—O41.405 (3)
C5—N31.465 (3)C11—N51.444 (3)
C5—H5A0.9700C11—H11A0.9700
C5—H5B0.9700C11—H11B0.9700
C6—O11.217 (3)O3—H3A0.8200
C6—N21.365 (3)O4—H40.8200
C6—N41.373 (3)
C3—C1—H1A109.5N2—C8—H8111.8
C3—C1—H1B109.5N3—C8—H8111.8
H1A—C1—H1B109.5C9—C8—H8111.8
C3—C1—H1C109.5N4—C9—N5115.56 (19)
H1A—C1—H1C109.5N4—C9—C8102.54 (17)
H1B—C1—H1C109.5N5—C9—C8102.27 (18)
C3—C2—H2A109.5N4—C9—H9111.9
C3—C2—H2B109.5N5—C9—H9111.9
H2A—C2—H2B109.5C8—C9—H9111.9
C3—C2—H2C109.5O3—C10—N4110.3 (2)
H2A—C2—H2C109.5O3—C10—H10A109.6
H2B—C2—H2C109.5N4—C10—H10A109.6
N1—C3—C2109.95 (18)O3—C10—H10B109.6
N1—C3—C1111.41 (19)N4—C10—H10B109.6
C2—C3—C1109.16 (19)H10A—C10—H10B108.1
N1—C3—H3108.8O4—C11—N5113.1 (2)
C2—C3—H3108.8O4—C11—H11A109.0
C1—C3—H3108.8N5—C11—H11A109.0
N1—C4—N2113.19 (18)O4—C11—H11B109.0
N1—C4—H4A108.9N5—C11—H11B109.0
N2—C4—H4A108.9H11A—C11—H11B107.8
N1—C4—H4B108.9C4—N1—C5107.56 (18)
N2—C4—H4B108.9C4—N1—C3115.17 (18)
H4A—C4—H4B107.8C5—N1—C3113.06 (18)
N1—C5—N3113.94 (18)C6—N2—C8112.04 (19)
N1—C5—H5A108.8C6—N2—C4126.1 (2)
N3—C5—H5A108.8C8—N2—C4116.68 (19)
N1—C5—H5B108.8C7—N3—C8110.27 (18)
N3—C5—H5B108.8C7—N3—C5121.59 (19)
H5A—C5—H5B107.7C8—N3—C5115.81 (18)
O1—C6—N2126.1 (2)C6—N4—C10123.1 (2)
O1—C6—N4126.1 (2)C6—N4—C9112.54 (19)
N2—C6—N4107.7 (2)C10—N4—C9124.3 (2)
O2—C7—N5126.0 (2)C7—N5—C11123.5 (2)
O2—C7—N3124.6 (2)C7—N5—C9112.35 (19)
N5—C7—N3109.3 (2)C11—N5—C9123.8 (2)
N2—C8—N3112.04 (18)C10—O3—H3A109.5
N2—C8—C9103.90 (18)C11—O4—H4109.5
N3—C8—C9105.15 (18)
N2—C8—C9—N48.6 (2)N2—C8—N3—C7103.9 (2)
N3—C8—C9—N4126.46 (17)C9—C8—N3—C78.3 (2)
N2—C8—C9—N5111.47 (18)N2—C8—N3—C539.1 (3)
N3—C8—C9—N56.4 (2)C9—C8—N3—C5151.36 (18)
N2—C4—N1—C556.0 (2)N1—C5—N3—C788.5 (3)
N2—C4—N1—C371.1 (3)N1—C5—N3—C850.0 (3)
N3—C5—N1—C456.3 (2)O1—C6—N4—C109.9 (4)
N3—C5—N1—C372.0 (2)N2—C6—N4—C10167.19 (19)
C2—C3—N1—C4169.44 (19)O1—C6—N4—C9173.0 (2)
C1—C3—N1—C448.3 (2)N2—C6—N4—C99.9 (3)
C2—C3—N1—C566.3 (2)O3—C10—N4—C693.0 (3)
C1—C3—N1—C5172.50 (18)O3—C10—N4—C990.2 (3)
O1—C6—N2—C8179.3 (2)N5—C9—N4—C698.8 (2)
N4—C6—N2—C83.6 (2)C8—C9—N4—C611.6 (2)
O1—C6—N2—C425.9 (4)N5—C9—N4—C1084.2 (3)
N4—C6—N2—C4157.0 (2)C8—C9—N4—C10165.5 (2)
N3—C8—N2—C6116.5 (2)O2—C7—N5—C116.7 (3)
C9—C8—N2—C63.5 (2)N3—C7—N5—C11170.57 (19)
N3—C8—N2—C439.7 (3)O2—C7—N5—C9179.7 (2)
C9—C8—N2—C4152.66 (18)N3—C7—N5—C92.4 (2)
N1—C4—N2—C6102.0 (2)O4—C11—N5—C792.8 (3)
N1—C4—N2—C850.3 (3)O4—C11—N5—C995.0 (3)
O2—C7—N3—C8175.7 (2)N4—C9—N5—C7113.2 (2)
N5—C7—N3—C86.9 (2)C8—C9—N5—C72.7 (2)
O2—C7—N3—C535.2 (3)N4—C9—N5—C1173.8 (3)
N5—C7—N3—C5147.45 (19)C8—C9—N5—C11175.65 (19)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C5—H5B···O20.972.592.925 (3)101
O4—H4···O30.821.922.728 (3)168
C10—H10B···O4i0.972.583.494 (3)157
O3—H3A···O2i0.821.902.713 (2)173
Symmetry code: (i) x1/2, y+1/2, z.
 

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