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The title compound, C14H21N5O7, is a glycoluril derivative. The mol­ecule is built up from three fused rings. The triazine six-membered ring displays a normal chair conformation.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806053244/xu2178sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806053244/xu2178Isup2.hkl
Contains datablock I

CCDC reference: 634080

Key indicators

  • Single-crystal X-ray study
  • T = 292 K
  • Mean [sigma](C-C) = 0.009 Å
  • Disorder in main residue
  • R factor = 0.050
  • wR factor = 0.152
  • Data-to-parameter ratio = 6.4

checkCIF/PLATON results

No syntax errors found



Alert level B PLAT220_ALERT_2_B Large Non-Solvent C Ueq(max)/Ueq(min) ... 4.20 Ratio PLAT222_ALERT_3_B Large Non-Solvent H Ueq(max)/Ueq(min) ... 4.39 Ratio
Alert level C PLAT089_ALERT_3_C Poor Data / Parameter Ratio (Zmax .LT. 18) ..... 6.36 PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C13 PLAT301_ALERT_3_C Main Residue Disorder ......................... 7.00 Perc. PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 9 PLAT731_ALERT_1_C Bond Calc 0.82(5), Rep 0.82(2) ...... 2.50 su-Ra O1 -H1 1.555 1.555 PLAT735_ALERT_1_C D-H Calc 0.82(5), Rep 0.82(2) ...... 2.50 su-Ra O1 -H1 1.555 1.555
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 26.00 From the CIF: _reflns_number_total 1659 Count of symmetry unique reflns 1669 Completeness (_total/calc) 99.40% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 0 Fraction of Friedel pairs measured 0.000 Are heavy atom types Z>Si present no
0 ALERT level A = In general: serious problem 2 ALERT level B = Potentially serious problem 6 ALERT level C = Check and explain 1 ALERT level G = General alerts; check 2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 2 ALERT type 2 Indicator that the structure model may be wrong or deficient 4 ALERT type 3 Indicator that the structure quality may be low 1 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check

Computing details top

Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 2000); software used to prepare material for publication: SHELXTL.

Diethyl 6-(2-hydroxyethyl)-1,4-dioxo-2,2a,3,4,6,7-hexahydro-1H,5H- 2,3,4a,6,7a-pentaazacyclopenta[cd]indene-2a,7 b-dicarboxylate top
Crystal data top
C14H21N5O7F(000) = 784
Mr = 371.36Dx = 1.453 Mg m3
Monoclinic, CcMo Kα radiation, λ = 0.71073 Å
Hall symbol: C -2ycCell parameters from 1526 reflections
a = 17.867 (4) Åθ = 2.8–22.1°
b = 11.871 (2) ŵ = 0.12 mm1
c = 8.8912 (17) ÅT = 292 K
β = 115.793 (3)°Block, colorless
V = 1698.0 (6) Å30.30 × 0.20 × 0.10 mm
Z = 4
Data collection top
Bruker SMART CCD area-detector
diffractometer
1354 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.073
Graphite monochromatorθmax = 26.0°, θmin = 2.1°
φ and ω scansh = 1622
5110 measured reflectionsk = 1414
1659 independent reflectionsl = 1010
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)] = 0.050Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.152H atoms treated by a mixture of independent and constrained refinement
S = 1.06 w = 1/[σ2(Fo2) + (0.0939P)2]
where P = (Fo2 + 2Fc2)/3
1659 reflections(Δ/σ)max < 0.001
261 parametersΔρmax = 0.39 e Å3
19 restraintsΔρmin = 0.56 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*/UeqOcc. (<1)
C10.0424 (4)0.2457 (5)0.2586 (7)0.0471 (14)
H1A0.01280.17680.26080.056*
H1B0.10100.22750.21640.056*
C20.0114 (4)0.2913 (5)0.4342 (6)0.0406 (12)
H2A0.04380.35690.43360.049*
H2B0.01880.23470.50520.049*
C30.1022 (3)0.4103 (5)0.6276 (6)0.0376 (12)
H3A0.06180.47080.58860.045*
H3B0.15530.44060.64170.045*
C40.1322 (3)0.2271 (5)0.5602 (6)0.0374 (12)
H4A0.18670.24880.57150.045*
H4B0.11150.16730.47800.045*
C50.0446 (3)0.3769 (4)0.8355 (6)0.0316 (11)
C60.0965 (3)0.0955 (4)0.7394 (6)0.0296 (10)
C70.1578 (3)0.2679 (4)0.8529 (5)0.0286 (10)
C80.2509 (4)0.2960 (4)0.9385 (6)0.0372 (12)
C90.3562 (4)0.3844 (7)1.1760 (9)0.0646 (19)
H9A0.37980.42841.11530.077*
H9B0.38670.31421.21080.077*
C100.3604 (5)0.4475 (9)1.3221 (10)0.091 (3)
H10A0.34540.52461.29140.137*
H10B0.41600.44411.40980.137*
H10C0.32270.41491.36040.137*
C110.1187 (3)0.2150 (4)0.9656 (6)0.0286 (10)
C120.1800 (4)0.1995 (4)1.1498 (6)0.0380 (12)
N10.0771 (3)0.3224 (4)0.5022 (5)0.0362 (10)
N20.1098 (2)0.3705 (3)0.7900 (4)0.0304 (9)
N30.1397 (3)0.1848 (3)0.7218 (4)0.0295 (9)
N40.0533 (3)0.2934 (3)0.9440 (5)0.0352 (10)
H40.02260.28740.99590.042*
N50.0897 (3)0.1082 (3)0.8851 (5)0.0340 (10)
H50.06970.05680.92540.041*
O10.0314 (3)0.3240 (4)0.1497 (4)0.0453 (9)
H10.042 (5)0.388 (3)0.168 (10)0.068*
O20.0083 (2)0.4493 (3)0.7876 (5)0.0430 (9)
O30.0684 (3)0.0167 (3)0.6410 (5)0.0466 (10)
O40.2997 (3)0.2643 (4)0.8920 (5)0.0594 (12)
O50.2677 (2)0.3622 (4)1.0703 (4)0.0493 (10)
O60.1718 (3)0.2469 (4)1.2615 (5)0.0611 (12)
O70.2394 (3)0.1302 (4)1.1651 (5)0.0565 (11)
C130.3101 (6)0.1175 (7)1.3288 (9)0.053 (3)0.77 (3)
H13A0.36020.10251.31550.064*0.77 (3)
H13B0.31820.18641.39270.064*0.77 (3)
C140.2932 (8)0.0241 (11)1.4162 (15)0.095 (6)0.77 (3)
H14A0.25170.04641.45160.142*0.77 (3)
H14B0.34330.00401.51210.142*0.77 (3)
H14C0.27350.03951.34260.142*0.77 (3)
C14'0.335 (4)0.004 (5)1.361 (8)0.12 (2)0.23 (3)
H14D0.30990.05251.27630.180*0.23 (3)
H14E0.35210.02991.46930.180*0.23 (3)
H14F0.38270.03481.35260.180*0.23 (3)
C13'0.275 (3)0.093 (4)1.339 (2)0.075 (14)0.23 (3)
H13C0.30270.15521.41240.090*0.23 (3)
H13D0.23180.06481.36650.090*0.23 (3)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.044 (3)0.059 (3)0.032 (3)0.002 (3)0.010 (2)0.001 (2)
C20.046 (3)0.054 (3)0.026 (2)0.003 (3)0.020 (2)0.007 (2)
C30.041 (3)0.044 (3)0.029 (3)0.002 (2)0.016 (2)0.010 (2)
C40.045 (3)0.050 (3)0.023 (2)0.001 (2)0.020 (2)0.001 (2)
C50.038 (3)0.031 (2)0.022 (2)0.001 (2)0.010 (2)0.0048 (19)
C60.029 (3)0.031 (2)0.027 (2)0.0079 (19)0.0104 (19)0.0003 (18)
C70.034 (3)0.034 (2)0.021 (2)0.000 (2)0.014 (2)0.0001 (18)
C80.039 (3)0.044 (3)0.028 (2)0.003 (2)0.014 (2)0.002 (2)
C90.036 (3)0.093 (5)0.053 (4)0.014 (3)0.009 (3)0.006 (4)
C100.049 (4)0.126 (7)0.073 (6)0.023 (5)0.003 (4)0.047 (5)
C110.032 (3)0.033 (2)0.022 (2)0.0018 (19)0.013 (2)0.0014 (17)
C120.039 (3)0.048 (3)0.029 (3)0.001 (2)0.016 (2)0.004 (2)
N10.046 (3)0.043 (2)0.022 (2)0.003 (2)0.0176 (19)0.0054 (17)
N20.035 (2)0.032 (2)0.023 (2)0.0022 (17)0.0120 (17)0.0019 (16)
N30.038 (2)0.035 (2)0.0188 (18)0.0009 (18)0.0145 (16)0.0006 (16)
N40.040 (3)0.043 (2)0.031 (2)0.0052 (19)0.023 (2)0.0049 (18)
N50.047 (3)0.031 (2)0.025 (2)0.0044 (18)0.0168 (19)0.0026 (16)
O10.053 (2)0.061 (2)0.0250 (17)0.004 (2)0.0198 (17)0.0015 (17)
O20.050 (2)0.041 (2)0.0369 (19)0.0131 (18)0.0184 (17)0.0004 (16)
O30.067 (3)0.0381 (19)0.037 (2)0.0015 (19)0.0246 (18)0.0101 (16)
O40.039 (3)0.098 (3)0.048 (3)0.005 (2)0.025 (2)0.015 (2)
O50.031 (2)0.074 (3)0.038 (2)0.0105 (19)0.0102 (18)0.0147 (19)
O60.069 (3)0.092 (3)0.024 (2)0.007 (3)0.022 (2)0.006 (2)
O70.060 (3)0.065 (3)0.033 (2)0.023 (2)0.0095 (19)0.0084 (19)
C130.043 (5)0.068 (6)0.037 (4)0.008 (4)0.007 (4)0.016 (4)
C140.066 (8)0.092 (8)0.082 (8)0.021 (7)0.009 (6)0.050 (7)
C14'0.12 (2)0.12 (2)0.12 (2)0.0001 (11)0.052 (9)0.0000 (11)
C13'0.075 (14)0.075 (14)0.075 (14)0.0000 (11)0.033 (6)0.0002 (11)
Geometric parameters (Å, º) top
C1—O11.417 (7)C9—C101.473 (11)
C1—C21.511 (8)C9—H9A0.9700
C1—H1A0.9700C9—H9B0.9700
C1—H1B0.9700C10—H10A0.9600
C2—N11.473 (7)C10—H10B0.9600
C2—H2A0.9700C10—H10C0.9600
C2—H2B0.9700C11—N51.437 (6)
C3—N11.448 (7)C11—N41.439 (6)
C3—N21.468 (6)C11—C121.535 (7)
C3—H3A0.9700C12—O61.204 (7)
C3—H3B0.9700C12—O71.302 (7)
C4—N11.439 (7)N4—H40.8600
C4—N31.471 (6)N5—H50.8600
C4—H4A0.9700O1—H10.82 (2)
C4—H4B0.9700O7—C13'1.461 (11)
C5—O21.210 (6)O7—C131.462 (7)
C5—N41.344 (6)C13—C141.459 (9)
C5—N21.392 (6)C13—H13A0.9700
C6—O31.228 (6)C13—H13B0.9700
C6—N51.361 (6)C14—H14A0.9600
C6—N31.361 (6)C14—H14B0.9600
C7—N31.452 (6)C14—H14C0.9600
C7—N21.454 (6)C14'—C13'1.452 (11)
C7—C81.536 (7)C14'—H14D0.9600
C7—C111.580 (6)C14'—H14E0.9600
C8—O41.177 (7)C14'—H14F0.9600
C8—O51.332 (6)C13'—H13C0.9700
C9—O51.469 (7)C13'—H13D0.9700
O1—C1—C2112.0 (5)H10A—C10—H10C109.5
O1—C1—H1A109.2H10B—C10—H10C109.5
C2—C1—H1A109.2N5—C11—N4114.1 (4)
O1—C1—H1B109.2N5—C11—C12111.2 (4)
C2—C1—H1B109.2N4—C11—C12112.4 (4)
H1A—C1—H1B107.9N5—C11—C7101.4 (4)
N1—C2—C1111.1 (5)N4—C11—C7102.4 (3)
N1—C2—H2A109.4C12—C11—C7114.7 (4)
C1—C2—H2A109.4O6—C12—O7126.5 (5)
N1—C2—H2B109.4O6—C12—C11122.5 (5)
C1—C2—H2B109.4O7—C12—C11111.0 (4)
H2A—C2—H2B108.0C4—N1—C3110.8 (4)
N1—C3—N2113.0 (4)C4—N1—C2113.3 (4)
N1—C3—H3A109.0C3—N1—C2114.5 (4)
N2—C3—H3A109.0C5—N2—C7111.2 (4)
N1—C3—H3B109.0C5—N2—C3122.5 (4)
N2—C3—H3B109.0C7—N2—C3115.7 (4)
H3A—C3—H3B107.8C6—N3—C7112.1 (4)
N1—C4—N3112.1 (4)C6—N3—C4124.3 (4)
N1—C4—H4A109.2C7—N3—C4116.5 (4)
N3—C4—H4A109.2C5—N4—C11114.0 (4)
N1—C4—H4B109.2C5—N4—H4123.0
N3—C4—H4B109.2C11—N4—H4123.0
H4A—C4—H4B107.9C6—N5—C11114.2 (4)
O2—C5—N4127.3 (5)C6—N5—H5122.9
O2—C5—N2124.1 (4)C11—N5—H5122.9
N4—C5—N2108.6 (4)C1—O1—H1111 (6)
O3—C6—N5125.7 (5)C8—O5—C9115.9 (5)
O3—C6—N3126.0 (4)C12—O7—C13'105.5 (15)
N5—C6—N3108.3 (4)C12—O7—C13118.7 (5)
N3—C7—N2111.8 (4)C14—C13—O7108.6 (8)
N3—C7—C8111.1 (4)C14—C13—H13A110.0
N2—C7—C8109.8 (4)O7—C13—H13A110.0
N3—C7—C11103.5 (4)C14—C13—H13B110.0
N2—C7—C11103.2 (4)O7—C13—H13B110.0
C8—C7—C11117.1 (4)H13A—C13—H13B108.3
O4—C8—O5125.5 (5)C13'—C14'—H14D109.5
O4—C8—C7124.4 (5)C13'—C14'—H14E109.5
O5—C8—C7110.2 (4)H14D—C14'—H14E109.5
O5—C9—C10106.5 (6)C13'—C14'—H14F109.5
O5—C9—H9A110.4H14D—C14'—H14F109.5
C10—C9—H9A110.4H14E—C14'—H14F109.5
O5—C9—H9B110.4C14'—C13'—O7109 (3)
C10—C9—H9B110.4C14'—C13'—H13C109.9
H9A—C9—H9B108.6O7—C13'—H13C109.9
C9—C10—H10A109.5C14'—C13'—H13D109.9
C9—C10—H10B109.5O7—C13'—H13D109.9
H10A—C10—H10B109.5H13C—C13'—H13D108.3
C9—C10—H10C109.5
O1—C1—C2—N157.7 (6)C11—C7—N2—C3152.2 (4)
N3—C7—C8—O48.0 (7)N1—C3—N2—C592.5 (5)
N2—C7—C8—O4116.3 (6)N1—C3—N2—C749.1 (6)
C11—C7—C8—O4126.6 (6)O3—C6—N3—C7175.0 (5)
N3—C7—C8—O5172.9 (4)N5—C6—N3—C75.0 (5)
N2—C7—C8—O562.8 (5)O3—C6—N3—C425.9 (7)
C11—C7—C8—O554.3 (6)N5—C6—N3—C4154.2 (4)
N3—C7—C11—N53.3 (5)N2—C7—N3—C6109.5 (4)
N2—C7—C11—N5120.0 (4)C8—C7—N3—C6127.3 (4)
C8—C7—C11—N5119.3 (4)C11—C7—N3—C60.9 (5)
N3—C7—C11—N4114.8 (4)N2—C7—N3—C442.2 (5)
N2—C7—C11—N41.9 (4)C8—C7—N3—C480.9 (5)
C8—C7—C11—N4122.6 (4)C11—C7—N3—C4152.6 (4)
N3—C7—C11—C12123.2 (4)N1—C4—N3—C698.0 (5)
N2—C7—C11—C12120.1 (4)N1—C4—N3—C749.9 (6)
C8—C7—C11—C120.6 (6)O2—C5—N4—C11175.3 (5)
N5—C11—C12—O6127.7 (6)N2—C5—N4—C117.4 (5)
N4—C11—C12—O61.5 (7)N5—C11—N4—C5105.5 (5)
C7—C11—C12—O6118.0 (6)C12—C11—N4—C5126.8 (4)
N5—C11—C12—O752.2 (6)C7—C11—N4—C53.2 (5)
N4—C11—C12—O7178.6 (4)O3—C6—N5—C11172.3 (5)
C7—C11—C12—O762.1 (6)N3—C6—N5—C117.7 (5)
N3—C4—N1—C354.4 (5)N4—C11—N5—C6102.5 (5)
N3—C4—N1—C275.9 (5)C12—C11—N5—C6129.1 (4)
N2—C3—N1—C454.5 (5)C7—C11—N5—C66.8 (5)
N2—C3—N1—C275.1 (5)O4—C8—O5—C98.1 (8)
C1—C2—N1—C478.8 (5)C7—C8—O5—C9172.8 (5)
C1—C2—N1—C3152.8 (4)C10—C9—O5—C8173.7 (6)
O2—C5—N2—C7173.9 (4)O6—C12—O7—C13'19 (2)
N4—C5—N2—C78.6 (5)C11—C12—O7—C13'161 (2)
O2—C5—N2—C330.8 (7)O6—C12—O7—C138.8 (9)
N4—C5—N2—C3151.8 (4)C11—C12—O7—C13171.3 (6)
N3—C7—N2—C5104.3 (4)C12—O7—C13—C1492.4 (11)
C8—C7—N2—C5131.9 (4)C13'—O7—C13—C1424 (3)
C11—C7—N2—C56.3 (5)C12—O7—C13'—C14'173 (4)
N3—C7—N2—C341.5 (5)C13—O7—C13'—C14'65 (4)
C8—C7—N2—C382.3 (5)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1···O2i0.82 (2)2.16 (4)2.911 (6)152 (8)
N4—H4···O1ii0.862.032.860 (5)161
N5—H5···O3iii0.862.122.877 (5)147
C3—H3A···O2i0.972.593.260 (6)126
C13—H13A···O2iv0.972.543.511 (11)176
Symmetry codes: (i) x, y+1, z1/2; (ii) x, y, z+1; (iii) x, y, z+1/2; (iv) x+1/2, y+1/2, z+1/2.
 

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