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The title compound, C20H21IN4O7, is a glycoluril derivative which contains five fused rings. An iodo­benzene ring is fused to a seven-membered ring linked to two of the N atoms from the separate rings of the glycoluril system, and the other two N atoms are linked to an O atom by two of the methyl­ene groups. The structure of the compound possesses normal geometrical parameters. The crystal packing is consolidated by inter­molecular hydrogen bonds, resulting in a two-dimensional network.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806016011/at2031sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806016011/at2031Isup2.hkl
Contains datablock I

CCDC reference: 610685

Key indicators

  • Single-crystal X-ray study
  • T = 292 K
  • Mean [sigma](C-C) = 0.007 Å
  • Disorder in main residue
  • R factor = 0.059
  • wR factor = 0.148
  • Data-to-parameter ratio = 16.1

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 0.134 PLAT020_ALERT_3_C The value of Rint is greater than 0.10 ......... 0.13 PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 3.37 Ratio PLAT222_ALERT_3_C Large Non-Solvent H Ueq(max)/Ueq(min) ... 3.73 Ratio PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C16 PLAT301_ALERT_3_C Main Residue Disorder ......................... 3.00 Perc. PLAT360_ALERT_2_C Short C(sp3)-C(sp3) Bond C17 - C18 ... 1.42 Ang. PLAT431_ALERT_2_C Short Inter HL..A Contact I1 .. O3 .. 3.37 Ang.
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 8 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 4 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 0 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: SMART (Bruker, 2001); cell refinement: SAINT-Plus (Bruker, 2001); data reduction: SAINT-Plus; 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.

Diethyl 5,10-dihydro-6-iodo-4,11-dioxo-cis-1H,3H,4H,11H-2-oxa-3a,4a,10a,11a- tetraazazbenz[f]indeno[2,1,7-ija]azulene-11b,11c-dicarboxylate top
Crystal data top
C20H21IN4O7F(000) = 2224
Mr = 556.31Dx = 1.736 Mg m3
Orthorhombic, PbcaMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2abCell parameters from 4829 reflections
a = 15.533 (6) Åθ = 2.4–19.7°
b = 11.414 (5) ŵ = 1.56 mm1
c = 24.006 (10) ÅT = 292 K
V = 4256 (3) Å3Block, colorless
Z = 80.10 × 0.05 × 0.02 mm
Data collection top
Bruker APEX CCD area-detector
diffractometer
2978 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.134
Graphite monochromatorθmax = 27.5°, θmin = 1.7°
φ and ω scansh = 2020
46045 measured reflectionsk = 1414
4856 independent reflectionsl = 3131
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)] = 0.059Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.148H-atom parameters constrained
S = 0.94 w = 1/[σ2(Fo2) + (0.075P)2]
where P = (Fo2 + 2Fc2)/3
4856 reflections(Δ/σ)max = 0.001
301 parametersΔρmax = 0.97 e Å3
2 restraintsΔρmin = 0.92 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)
C10.1317 (3)0.6780 (4)1.0936 (2)0.0352 (11)
C20.1706 (4)0.7379 (5)1.1377 (2)0.0514 (15)
H20.15490.72151.17430.062*
C30.2314 (4)0.8198 (6)1.1269 (2)0.0584 (17)
H30.25740.85991.15610.070*
C40.2551 (3)0.8444 (5)1.0722 (2)0.0470 (13)
H40.29630.90171.06520.056*
C50.2181 (3)0.7849 (4)1.02803 (19)0.0290 (10)
C60.1542 (3)0.6992 (4)1.03898 (18)0.0282 (10)
C70.1162 (3)0.6302 (4)0.98996 (17)0.0274 (10)
H7A0.16240.58810.97160.033*
H7B0.07630.57251.00450.033*
C80.2459 (3)0.8138 (4)0.9703 (2)0.0326 (11)
H8A0.28950.87460.97220.039*
H8B0.27250.74490.95410.039*
C90.0100 (3)0.7451 (4)0.95908 (18)0.0266 (10)
C100.1498 (3)0.9652 (4)0.93250 (19)0.0283 (10)
C110.1183 (3)0.7711 (4)0.90862 (17)0.0244 (9)
C120.1670 (3)0.6994 (4)0.8643 (2)0.0328 (11)
C130.2020 (4)0.5120 (5)0.8299 (2)0.0457 (13)
H13A0.19790.43210.84340.055*
H13B0.26170.53610.83240.055*
C140.1739 (4)0.5161 (6)0.7703 (2)0.0635 (18)
H14A0.11460.49330.76770.095*
H14B0.20860.46320.74870.095*
H14C0.18070.59430.75620.095*
C150.0478 (3)0.8542 (4)0.88474 (18)0.0286 (10)
C160.0284 (3)0.8433 (5)0.8222 (2)0.0418 (12)
C170.0194 (4)0.7153 (6)0.7512 (2)0.0608 (17)
H17A0.00760.78350.72830.073*
H17B0.01610.65130.73770.073*
C180.1074 (4)0.6844 (7)0.7459 (3)0.082 (2)
H18A0.11930.61740.76880.123*
H18B0.11980.66600.70780.123*
H18C0.14260.74890.75770.123*
C190.0916 (3)0.9155 (4)0.9240 (2)0.0371 (12)
H19A0.11950.93260.88880.044*
H19B0.13540.88960.95010.044*
C200.0122 (4)1.0592 (4)0.9075 (3)0.0449 (13)
H20A0.03881.12930.92260.054*
H20B0.01461.07980.87240.054*
I10.03876 (3)0.55284 (4)1.115638 (16)0.05707 (18)
N10.0717 (2)0.7007 (3)0.94882 (14)0.0227 (8)
N20.1777 (2)0.8530 (3)0.93373 (15)0.0259 (8)
N30.0293 (2)0.8235 (3)0.91626 (15)0.0265 (8)
N40.0782 (2)0.9709 (3)0.89786 (15)0.0288 (8)
O10.05713 (19)0.7168 (3)0.99608 (14)0.0371 (8)
O20.18354 (19)1.0479 (2)0.95556 (14)0.0354 (8)
O30.1493 (2)0.5883 (3)0.86506 (14)0.0346 (8)
O40.2156 (3)0.7454 (3)0.83333 (19)0.0789 (15)
O50.0257 (10)0.9260 (6)0.7911 (3)0.081 (5)0.78 (2)
O5'0.093 (2)0.871 (4)0.7905 (8)0.079 (15)0.22 (2)
O60.0030 (3)0.7408 (4)0.80865 (15)0.0592 (11)
O70.0516 (2)1.0192 (3)0.94482 (16)0.0423 (9)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.031 (3)0.034 (3)0.041 (3)0.001 (2)0.001 (2)0.003 (2)
C20.049 (3)0.069 (4)0.036 (3)0.003 (3)0.001 (3)0.014 (3)
C30.051 (4)0.081 (5)0.043 (3)0.005 (3)0.013 (3)0.025 (3)
C40.034 (3)0.044 (3)0.063 (4)0.004 (2)0.007 (3)0.011 (3)
C50.022 (2)0.026 (2)0.039 (3)0.0061 (18)0.004 (2)0.0040 (19)
C60.024 (2)0.024 (2)0.036 (3)0.0095 (19)0.0014 (19)0.0022 (19)
C70.027 (2)0.022 (2)0.033 (2)0.0010 (18)0.0066 (19)0.0016 (18)
C80.023 (2)0.020 (2)0.055 (3)0.0009 (18)0.001 (2)0.003 (2)
C90.023 (2)0.028 (2)0.028 (3)0.0054 (19)0.0007 (19)0.0069 (19)
C100.025 (2)0.022 (2)0.038 (3)0.0006 (19)0.010 (2)0.0010 (19)
C110.028 (2)0.019 (2)0.026 (2)0.0046 (18)0.0044 (18)0.0026 (17)
C120.032 (3)0.025 (2)0.042 (3)0.002 (2)0.006 (2)0.009 (2)
C130.056 (4)0.032 (3)0.049 (3)0.016 (3)0.009 (3)0.011 (2)
C140.078 (5)0.059 (4)0.054 (4)0.013 (3)0.002 (3)0.025 (3)
C150.024 (2)0.028 (2)0.034 (2)0.0011 (18)0.003 (2)0.001 (2)
C160.050 (3)0.042 (3)0.034 (3)0.009 (3)0.004 (2)0.001 (2)
C170.070 (4)0.078 (5)0.034 (3)0.005 (4)0.007 (3)0.020 (3)
C180.069 (5)0.102 (6)0.075 (5)0.008 (4)0.022 (4)0.013 (4)
C190.021 (2)0.039 (3)0.051 (3)0.005 (2)0.004 (2)0.000 (2)
C200.041 (3)0.031 (3)0.063 (4)0.011 (2)0.007 (3)0.001 (3)
I10.0702 (3)0.0542 (3)0.0468 (3)0.01104 (19)0.01784 (19)0.00370 (18)
N10.0233 (18)0.0168 (18)0.0281 (19)0.0018 (15)0.0048 (15)0.0001 (14)
N20.0207 (18)0.0171 (18)0.040 (2)0.0018 (15)0.0008 (15)0.0043 (16)
N30.0181 (18)0.032 (2)0.030 (2)0.0010 (16)0.0014 (15)0.0004 (16)
N40.028 (2)0.0202 (19)0.038 (2)0.0022 (16)0.0005 (17)0.0009 (15)
O10.0260 (18)0.043 (2)0.043 (2)0.0016 (15)0.0094 (15)0.0043 (16)
O20.0319 (18)0.0226 (17)0.052 (2)0.0043 (14)0.0009 (15)0.0110 (15)
O30.0393 (19)0.0212 (16)0.0433 (19)0.0018 (14)0.0112 (16)0.0073 (14)
O40.092 (3)0.046 (2)0.099 (4)0.032 (2)0.067 (3)0.031 (2)
O50.157 (13)0.047 (4)0.040 (3)0.009 (5)0.026 (4)0.012 (3)
O5'0.07 (2)0.13 (3)0.039 (11)0.05 (2)0.007 (10)0.002 (13)
O60.083 (3)0.059 (3)0.035 (2)0.022 (2)0.009 (2)0.0035 (19)
O70.034 (2)0.037 (2)0.056 (2)0.0098 (15)0.0013 (17)0.0056 (17)
Geometric parameters (Å, º) top
C1—C61.378 (6)C12—O31.297 (5)
C1—C21.399 (7)C13—O31.463 (5)
C1—I12.099 (5)C13—C141.496 (7)
C2—C31.354 (8)C13—H13A0.9700
C2—H20.9300C13—H13B0.9700
C3—C41.392 (8)C14—H14A0.9600
C3—H30.9300C14—H14B0.9600
C4—C51.384 (6)C14—H14C0.9600
C4—H40.9300C15—N41.448 (6)
C5—C61.418 (6)C15—N31.459 (5)
C5—C81.488 (6)C15—C161.537 (6)
C6—C71.534 (6)C16—O51.203 (7)
C7—N11.449 (5)C16—O61.276 (6)
C7—H7A0.9700C16—O5'1.30 (2)
C7—H7B0.9700C17—C181.417 (8)
C8—N21.448 (5)C17—O61.452 (6)
C8—H8A0.9700C17—H17A0.9700
C8—H8B0.9700C17—H17B0.9700
C9—O11.196 (5)C18—H18A0.9600
C9—N11.389 (5)C18—H18B0.9600
C9—N31.395 (6)C18—H18C0.9600
C10—O21.214 (5)C19—O71.427 (6)
C10—N21.352 (5)C19—N31.440 (6)
C10—N41.390 (6)C19—H19A0.9700
C11—N21.445 (5)C19—H19B0.9700
C11—N11.449 (5)C20—O71.411 (7)
C11—C121.541 (6)C20—N41.457 (6)
C11—C151.558 (6)C20—H20A0.9700
C12—O41.182 (6)C20—H20B0.9700
C6—C1—C2121.7 (5)C13—C14—H14C109.5
C6—C1—I1122.3 (3)H14A—C14—H14C109.5
C2—C1—I1116.0 (4)H14B—C14—H14C109.5
C3—C2—C1119.5 (5)N4—C15—N3112.1 (4)
C3—C2—H2120.2N4—C15—C16110.6 (4)
C1—C2—H2120.2N3—C15—C16109.0 (4)
C2—C3—C4120.4 (5)N4—C15—C11104.5 (3)
C2—C3—H3119.8N3—C15—C11103.9 (3)
C4—C3—H3119.8C16—C15—C11116.6 (4)
C5—C4—C3120.9 (5)O5—C16—O6123.4 (5)
C5—C4—H4119.6O5—C16—O5'58.2 (17)
C3—C4—H4119.6O6—C16—O5'108.4 (17)
C4—C5—C6119.2 (4)O5—C16—C15123.2 (5)
C4—C5—C8118.9 (4)O6—C16—C15112.6 (4)
C6—C5—C8121.9 (4)O5'—C16—C15113.5 (11)
C1—C6—C5118.3 (4)C18—C17—O6111.4 (5)
C1—C6—C7122.8 (4)C18—C17—H17A109.3
C5—C6—C7118.8 (4)O6—C17—H17A109.3
N1—C7—C6114.9 (3)C18—C17—H17B109.3
N1—C7—H7A108.5O6—C17—H17B109.3
C6—C7—H7A108.5H17A—C17—H17B108.0
N1—C7—H7B108.5C17—C18—H18A109.5
C6—C7—H7B108.5C17—C18—H18B109.5
H7A—C7—H7B107.5H18A—C18—H18B109.5
N2—C8—C5114.8 (4)C17—C18—H18C109.5
N2—C8—H8A108.6H18A—C18—H18C109.5
C5—C8—H8A108.6H18B—C18—H18C109.5
N2—C8—H8B108.6O7—C19—N3111.0 (3)
C5—C8—H8B108.6O7—C19—H19A109.4
H8A—C8—H8B107.5N3—C19—H19A109.4
O1—C9—N1126.3 (4)O7—C19—H19B109.4
O1—C9—N3126.1 (4)N3—C19—H19B109.4
N1—C9—N3107.5 (4)H19A—C19—H19B108.0
O2—C10—N2126.0 (4)O7—C20—N4111.8 (4)
O2—C10—N4125.6 (4)O7—C20—H20A109.3
N2—C10—N4108.3 (4)N4—C20—H20A109.3
N2—C11—N1113.5 (3)O7—C20—H20B109.3
N2—C11—C12108.5 (3)N4—C20—H20B109.3
N1—C11—C12114.2 (3)H20A—C20—H20B107.9
N2—C11—C15102.1 (3)C9—N1—C7121.2 (3)
N1—C11—C15103.4 (3)C9—N1—C11111.8 (3)
C12—C11—C15114.5 (4)C7—N1—C11121.6 (3)
O4—C12—O3125.3 (4)C10—N2—C11113.5 (4)
O4—C12—C11120.7 (4)C10—N2—C8122.7 (4)
O3—C12—C11113.9 (4)C11—N2—C8121.4 (3)
O3—C13—C14111.8 (4)C9—N3—C19121.1 (4)
O3—C13—H13A109.3C9—N3—C15111.1 (3)
C14—C13—H13A109.3C19—N3—C15116.3 (4)
O3—C13—H13B109.3C10—N4—C15110.4 (3)
C14—C13—H13B109.3C10—N4—C20120.0 (4)
H13A—C13—H13B107.9C15—N4—C20116.2 (4)
C13—C14—H14A109.5C12—O3—C13117.1 (4)
C13—C14—H14B109.5C16—O6—C17120.0 (5)
H14A—C14—H14B109.5C20—O7—C19110.6 (4)
C6—C1—C2—C30.7 (8)C15—C11—N1—C911.3 (4)
I1—C1—C2—C3179.9 (4)N2—C11—N1—C755.8 (5)
C1—C2—C3—C40.0 (9)C12—C11—N1—C769.4 (5)
C2—C3—C4—C50.9 (9)C15—C11—N1—C7165.5 (3)
C3—C4—C5—C61.1 (7)O2—C10—N2—C11172.2 (4)
C3—C4—C5—C8179.6 (5)N4—C10—N2—C1110.9 (5)
C2—C1—C6—C50.5 (7)O2—C10—N2—C89.6 (7)
I1—C1—C6—C5179.6 (3)N4—C10—N2—C8173.5 (4)
C2—C1—C6—C7176.6 (4)N1—C11—N2—C10105.3 (4)
I1—C1—C6—C72.6 (6)C12—C11—N2—C10126.6 (4)
C4—C5—C6—C10.4 (6)C15—C11—N2—C105.4 (4)
C8—C5—C6—C1179.7 (4)N1—C11—N2—C857.7 (5)
C4—C5—C6—C7177.6 (4)C12—C11—N2—C870.5 (5)
C8—C5—C6—C73.1 (6)C15—C11—N2—C8168.3 (3)
C1—C6—C7—N1121.4 (4)C5—C8—N2—C1083.3 (5)
C5—C6—C7—N161.6 (5)C5—C8—N2—C1178.1 (5)
C4—C5—C8—N2121.4 (4)O1—C9—N3—C1927.3 (7)
C6—C5—C8—N257.9 (5)N1—C9—N3—C19156.4 (4)
N2—C11—C12—O443.1 (6)O1—C9—N3—C15169.3 (4)
N1—C11—C12—O4170.8 (5)N1—C9—N3—C1514.4 (5)
C15—C11—C12—O470.2 (6)O7—C19—N3—C989.7 (5)
N2—C11—C12—O3136.8 (4)O7—C19—N3—C1550.4 (5)
N1—C11—C12—O39.1 (6)N4—C15—N3—C9105.0 (4)
C15—C11—C12—O3109.9 (4)C16—C15—N3—C9132.2 (4)
N2—C11—C15—N41.9 (4)C11—C15—N3—C97.2 (4)
N1—C11—C15—N4119.9 (3)N4—C15—N3—C1938.9 (5)
C12—C11—C15—N4115.2 (4)C16—C15—N3—C1983.8 (5)
N2—C11—C15—N3115.8 (3)C11—C15—N3—C19151.1 (4)
N1—C11—C15—N32.3 (4)O2—C10—N4—C15171.2 (4)
C12—C11—C15—N3127.2 (4)N2—C10—N4—C1511.9 (5)
N2—C11—C15—C16124.2 (4)O2—C10—N4—C2031.9 (7)
N1—C11—C15—C16117.7 (4)N2—C10—N4—C20151.2 (4)
C12—C11—C15—C167.2 (5)N3—C15—N4—C10103.6 (4)
N4—C15—C16—O511.2 (11)C16—C15—N4—C10134.5 (4)
N3—C15—C16—O5112.5 (10)C11—C15—N4—C108.3 (4)
C11—C15—C16—O5130.3 (10)N3—C15—N4—C2037.4 (5)
N4—C15—C16—O6178.7 (4)C16—C15—N4—C2084.4 (5)
N3—C15—C16—O657.7 (6)C11—C15—N4—C20149.3 (4)
C11—C15—C16—O659.5 (6)O7—C20—N4—C1088.7 (5)
N4—C15—C16—O5'55 (2)O7—C20—N4—C1548.4 (6)
N3—C15—C16—O5'179 (2)O4—C12—O3—C138.5 (8)
C11—C15—C16—O5'64 (2)C11—C12—O3—C13171.4 (4)
O1—C9—N1—C713.1 (6)C14—C13—O3—C1279.5 (6)
N3—C9—N1—C7170.6 (3)O5—C16—O6—C179.0 (12)
O1—C9—N1—C11167.5 (4)O5'—C16—O6—C1755 (2)
N3—C9—N1—C1116.2 (4)C15—C16—O6—C17179.2 (4)
C6—C7—N1—C975.8 (5)C18—C17—O6—C16117.0 (7)
C6—C7—N1—C1176.0 (5)N4—C20—O7—C1958.5 (5)
N2—C11—N1—C998.5 (4)N3—C19—O7—C2059.4 (5)
C12—C11—N1—C9136.4 (4)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C19—H19B···O2i0.972.493.251 (6)135
C13—H13A···O4ii0.972.533.302 (6)136
C8—H8B···O2ii0.972.353.246 (5)153
C7—H7A···O2ii0.972.473.353 (5)152
Symmetry codes: (i) x, y+2, z+2; (ii) x+1/2, y1/2, z.
 

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