Download citation
Download citation
link to html
The title compound, C20H22N4O7, is a glycoluril derivative with five fused rings. A benzene ring is fused to a seven-membered ring which includes two of the N atoms from separate rings of the glycoluril system, and the other two N atoms are linked to an O atom by two methyl­ene groups. The structure is stabilized by inter­molecular C—H...O hydrogen bonds.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S160053680604548X/sj2151sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S160053680604548X/sj2151Isup2.hkl
Contains datablock I

CCDC reference: 630470

Key indicators

  • Single-crystal X-ray study
  • T = 292 K
  • Mean [sigma](C-C) = 0.003 Å
  • Disorder in main residue
  • R factor = 0.052
  • wR factor = 0.145
  • Data-to-parameter ratio = 13.0

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for O6 PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C16 PLAT301_ALERT_3_C Main Residue Disorder ......................... 11.00 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 2 ALERT type 2 Indicator that the structure model may be wrong or deficient 1 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.

Diethyl cis-4,5,10,11-tetrahydro-4,11-dioxo-1H,3H-2-oxa-3a,4a,10a,11a- tetraazabenz[f]indeno[2,1,7-ija]azulene-11b,11c-dicarboxylate top
Crystal data top
C20H22N4O7Z = 2
Mr = 430.42F(000) = 452
Triclinic, P1Dx = 1.481 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 8.1503 (7) ÅCell parameters from 4793 reflections
b = 11.1548 (9) Åθ = 2.4–28.0°
c = 11.9935 (10) ŵ = 0.11 mm1
α = 95.016 (1)°T = 292 K
β = 104.297 (1)°Block, colorless
γ = 111.285 (1)°0.30 × 0.20 × 0.20 mm
V = 965.42 (14) Å3
Data collection top
Bruker SMART 4K CCD area-detector
diffractometer
3560 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.057
Graphite monochromatorθmax = 27.0°, θmin = 1.8°
φ and ω scansh = 1010
9092 measured reflectionsk = 1414
4167 independent reflectionsl = 1515
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)] = 0.052Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.145H-atom parameters constrained
S = 1.05 w = 1/[σ2(Fo2) + (0.0791P)2 + 0.1548P]
where P = (Fo2 + 2Fc2)/3
4167 reflections(Δ/σ)max < 0.001
321 parametersΔρmax = 0.24 e Å3
0 restraintsΔρmin = 0.36 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)
C10.5137 (2)0.98565 (16)0.15275 (12)0.0425 (4)
C20.7032 (3)1.02622 (19)0.17561 (15)0.0512 (4)
H20.75390.96390.17450.061*
C30.8173 (3)1.1577 (2)0.19990 (17)0.0587 (5)
H30.94411.18330.21520.070*
C40.7440 (3)1.2515 (2)0.20151 (16)0.0571 (4)
H40.82081.34010.21740.069*
C50.5550 (2)1.21236 (17)0.17932 (15)0.0499 (4)
H50.50561.27550.18060.060*
C60.4388 (2)1.08066 (16)0.15524 (12)0.0415 (3)
C70.2337 (2)1.04079 (16)0.13274 (14)0.0428 (4)
H7A0.20801.11910.13710.051*
H7B0.16980.98940.05380.051*
C80.3921 (2)0.84105 (16)0.12481 (14)0.0455 (4)
H8A0.30720.81960.04630.055*
H8B0.46880.79190.12470.055*
C90.17328 (19)1.02186 (14)0.32363 (13)0.0375 (3)
C100.3660 (2)0.77780 (14)0.31323 (13)0.0381 (3)
C110.1255 (2)0.82689 (14)0.20471 (12)0.0375 (3)
C120.0417 (2)0.74886 (16)0.09505 (14)0.0462 (4)
C130.2214 (7)0.5364 (4)0.0262 (4)0.0599 (12)0.650 (11)
H13A0.32480.55210.01230.072*0.650 (11)
H13B0.23890.44760.01640.072*0.650 (11)
C140.2235 (6)0.5462 (4)0.1486 (5)0.0710 (14)0.650 (11)
H14A0.21120.63280.16020.107*0.650 (11)
H14B0.33800.48280.20120.107*0.650 (11)
H14C0.12280.52950.16370.107*0.650 (11)
O40.0520 (6)0.6277 (4)0.0616 (4)0.0523 (8)0.650 (11)
C13'0.1549 (11)0.5883 (8)0.0784 (8)0.067 (2)0.350 (11)
H13C0.11000.53760.12340.081*0.350 (11)
H13D0.18500.64880.12460.081*0.350 (11)
O4'0.0103 (11)0.6624 (8)0.0303 (7)0.0529 (16)0.350 (11)
C14'0.3220 (18)0.4996 (9)0.0562 (10)0.092 (3)0.350 (11)
H14D0.29080.44420.00530.137*0.350 (11)
H14E0.40970.44640.12920.137*0.350 (11)
H14F0.37470.55020.01960.137*0.350 (11)
C150.0940 (2)0.79891 (14)0.32528 (13)0.0379 (3)
C160.0909 (2)0.68690 (17)0.31784 (16)0.0527 (4)
C170.2707 (3)0.5693 (3)0.4287 (2)0.0792 (7)
H17A0.30350.48820.37500.095*
H17B0.37300.59650.41000.095*
C180.2304 (3)0.5499 (2)0.5499 (3)0.0816 (7)
H18A0.12120.53210.56990.122*
H18B0.33250.47720.55790.122*
H18C0.21130.62770.60160.122*
C190.3193 (2)0.80113 (17)0.50840 (14)0.0477 (4)
H19A0.23290.74340.54280.057*
H19B0.43470.79030.53400.057*
C200.1833 (2)0.95187 (17)0.51293 (14)0.0459 (4)
H20A0.20691.04210.54280.055*
H20B0.09320.89530.54560.055*
N10.28543 (18)0.79847 (12)0.20624 (11)0.0392 (3)
N20.16151 (18)0.96462 (12)0.21522 (11)0.0386 (3)
N30.24632 (18)0.76400 (13)0.38069 (11)0.0404 (3)
N40.10930 (18)0.92333 (12)0.38535 (11)0.0399 (3)
O10.22311 (17)1.13822 (10)0.35886 (10)0.0494 (3)
O20.51105 (16)0.76594 (11)0.34206 (10)0.0486 (3)
O30.1558 (2)0.78822 (15)0.05582 (15)0.0812 (5)
O50.164 (2)0.5959 (6)0.2363 (5)0.110 (4)0.536 (19)
O5'0.2299 (5)0.6544 (15)0.2340 (4)0.089 (4)0.464 (19)
O60.1060 (2)0.66976 (17)0.41836 (14)0.0866 (5)
O70.34931 (16)0.93206 (12)0.54848 (10)0.0493 (3)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0519 (9)0.0563 (9)0.0273 (7)0.0283 (7)0.0143 (6)0.0115 (6)
C20.0563 (10)0.0722 (11)0.0409 (9)0.0372 (9)0.0211 (8)0.0190 (8)
C30.0490 (10)0.0812 (13)0.0496 (10)0.0259 (9)0.0187 (8)0.0210 (9)
C40.0556 (11)0.0622 (11)0.0493 (10)0.0167 (8)0.0170 (8)0.0166 (8)
C50.0587 (10)0.0543 (10)0.0434 (9)0.0265 (8)0.0179 (8)0.0168 (7)
C60.0487 (9)0.0528 (9)0.0287 (7)0.0254 (7)0.0116 (6)0.0129 (6)
C70.0502 (9)0.0484 (8)0.0370 (8)0.0275 (7)0.0113 (7)0.0152 (6)
C80.0573 (10)0.0538 (9)0.0339 (8)0.0323 (8)0.0139 (7)0.0058 (6)
C90.0354 (7)0.0405 (7)0.0376 (7)0.0197 (6)0.0069 (6)0.0051 (6)
C100.0435 (8)0.0343 (7)0.0350 (7)0.0189 (6)0.0052 (6)0.0032 (5)
C110.0423 (8)0.0375 (7)0.0324 (7)0.0200 (6)0.0054 (6)0.0048 (6)
C120.0507 (9)0.0471 (8)0.0372 (8)0.0251 (7)0.0006 (7)0.0023 (6)
C130.051 (2)0.0479 (19)0.058 (2)0.0075 (18)0.0001 (19)0.0069 (16)
C140.074 (2)0.063 (2)0.055 (3)0.0199 (18)0.002 (2)0.0087 (18)
O40.0480 (17)0.0424 (16)0.0538 (19)0.0182 (13)0.0016 (12)0.0048 (12)
C13'0.063 (4)0.071 (4)0.047 (5)0.019 (4)0.001 (4)0.012 (4)
O4'0.048 (3)0.046 (3)0.047 (3)0.015 (2)0.003 (2)0.010 (2)
C14'0.069 (6)0.061 (4)0.100 (7)0.002 (4)0.006 (5)0.004 (4)
C150.0384 (7)0.0388 (7)0.0342 (7)0.0165 (6)0.0054 (6)0.0062 (6)
C160.0489 (9)0.0489 (9)0.0470 (10)0.0093 (7)0.0074 (8)0.0089 (7)
C170.0437 (11)0.0868 (16)0.0887 (16)0.0024 (10)0.0178 (11)0.0373 (13)
C180.0747 (15)0.0695 (14)0.0983 (19)0.0182 (11)0.0310 (14)0.0363 (13)
C190.0479 (9)0.0615 (10)0.0341 (8)0.0239 (7)0.0079 (7)0.0149 (7)
C200.0487 (9)0.0528 (9)0.0359 (8)0.0193 (7)0.0149 (7)0.0045 (7)
N10.0453 (7)0.0431 (7)0.0327 (6)0.0247 (5)0.0075 (5)0.0063 (5)
N20.0456 (7)0.0385 (6)0.0345 (6)0.0214 (5)0.0099 (5)0.0077 (5)
N30.0434 (7)0.0454 (7)0.0336 (6)0.0218 (6)0.0061 (5)0.0108 (5)
N40.0430 (7)0.0418 (7)0.0354 (7)0.0177 (5)0.0120 (5)0.0050 (5)
O10.0581 (7)0.0389 (6)0.0511 (7)0.0233 (5)0.0125 (5)0.0022 (5)
O20.0494 (6)0.0551 (7)0.0456 (6)0.0317 (5)0.0059 (5)0.0071 (5)
O30.0692 (9)0.0642 (9)0.0877 (11)0.0398 (7)0.0264 (8)0.0115 (7)
O50.116 (7)0.063 (3)0.086 (3)0.028 (3)0.024 (3)0.0089 (19)
O5'0.039 (2)0.145 (8)0.043 (2)0.001 (2)0.0015 (13)0.011 (3)
O60.0529 (8)0.1032 (12)0.0628 (9)0.0134 (8)0.0128 (7)0.0240 (8)
O70.0458 (6)0.0608 (7)0.0337 (6)0.0170 (5)0.0077 (5)0.0029 (5)
Geometric parameters (Å, º) top
C1—C21.388 (2)C13—H13A0.9700
C1—C61.404 (2)C13—H13B0.9700
C1—C81.509 (2)C14—H14A0.9600
C2—C31.379 (3)C14—H14B0.9600
C2—H20.9300C14—H14C0.9600
C3—C41.381 (3)C13'—O4'1.454 (11)
C3—H30.9300C13'—C14'1.466 (15)
C4—C51.387 (3)C13'—H13C0.9700
C4—H40.9300C13'—H13D0.9700
C5—C61.385 (2)C14'—H14D0.9600
C5—H50.9300C14'—H14E0.9600
C6—C71.510 (2)C14'—H14F0.9600
C7—N21.456 (2)C15—N41.4547 (18)
C7—H7A0.9700C15—N31.4570 (18)
C7—H7B0.9700C15—C161.545 (2)
C8—N11.461 (2)C16—O51.200 (4)
C8—H8A0.9700C16—O5'1.225 (4)
C8—H8B0.9700C16—O61.266 (2)
C9—O11.2103 (17)C17—O61.445 (2)
C9—N21.3624 (19)C17—C181.463 (4)
C9—N41.394 (2)C17—H17A0.9700
C10—O21.2056 (18)C17—H17B0.9700
C10—N11.3699 (19)C18—H18A0.9600
C10—N31.390 (2)C18—H18B0.9600
C11—N21.4432 (18)C18—H18C0.9600
C11—N11.4454 (19)C19—O71.408 (2)
C11—C121.548 (2)C19—N31.460 (2)
C11—C151.568 (2)C19—H19A0.9700
C12—O31.181 (2)C19—H19B0.9700
C12—O4'1.321 (7)C20—O71.418 (2)
C12—O41.342 (4)C20—N41.458 (2)
C13—O41.458 (7)C20—H20A0.9700
C13—C141.477 (7)C20—H20B0.9700
C2—C1—C6119.04 (16)H13C—C13'—H13D107.9
C2—C1—C8119.75 (14)C12—O4'—C13'116.7 (6)
C6—C1—C8121.20 (15)C13'—C14'—H14D109.5
C3—C2—C1120.95 (16)C13'—C14'—H14E109.5
C3—C2—H2119.5H14D—C14'—H14E109.5
C1—C2—H2119.5C13'—C14'—H14F109.5
C2—C3—C4120.20 (18)H14D—C14'—H14F109.5
C2—C3—H3119.9H14E—C14'—H14F109.5
C4—C3—H3119.9N4—C15—N3112.53 (12)
C3—C4—C5119.48 (18)N4—C15—C16111.12 (13)
C3—C4—H4120.3N3—C15—C16109.44 (13)
C5—C4—H4120.3N4—C15—C11104.35 (11)
C6—C5—C4120.95 (16)N3—C15—C11103.54 (11)
C6—C5—H5119.5C16—C15—C11115.65 (12)
C4—C5—H5119.5O5—C16—O5'47.9 (3)
C5—C6—C1119.37 (16)O5—C16—O6120.0 (3)
C5—C6—C7119.88 (14)O5'—C16—O6119.8 (3)
C1—C6—C7120.74 (15)O5—C16—C15120.2 (5)
N2—C7—C6113.37 (12)O5'—C16—C15122.8 (5)
N2—C7—H7A108.9O6—C16—C15112.00 (15)
C6—C7—H7A108.9O6—C17—C18107.26 (19)
N2—C7—H7B108.9O6—C17—H17A110.3
C6—C7—H7B108.9C18—C17—H17A110.3
H7A—C7—H7B107.7O6—C17—H17B110.3
N1—C8—C1114.42 (12)C18—C17—H17B110.3
N1—C8—H8A108.7H17A—C17—H17B108.5
C1—C8—H8A108.7C17—C18—H18A109.5
N1—C8—H8B108.7C17—C18—H18B109.5
C1—C8—H8B108.7H18A—C18—H18B109.5
H8A—C8—H8B107.6C17—C18—H18C109.5
O1—C9—N2125.87 (14)H18A—C18—H18C109.5
O1—C9—N4125.54 (14)H18B—C18—H18C109.5
N2—C9—N4108.52 (12)O7—C19—N3111.64 (12)
O2—C10—N1126.07 (14)O7—C19—H19A109.3
O2—C10—N3125.47 (14)N3—C19—H19A109.3
N1—C10—N3108.33 (12)O7—C19—H19B109.3
N2—C11—N1113.63 (13)N3—C19—H19B109.3
N2—C11—C12108.97 (11)H19A—C19—H19B108.0
N1—C11—C12113.01 (12)O7—C20—N4110.78 (12)
N2—C11—C15102.35 (11)O7—C20—H20A109.5
N1—C11—C15103.12 (11)N4—C20—H20A109.5
C12—C11—C15115.33 (13)O7—C20—H20B109.5
O3—C12—O4'121.7 (3)N4—C20—H20B109.5
O3—C12—O4125.1 (2)H20A—C20—H20B108.1
O3—C12—C11122.45 (14)C10—N1—C11112.50 (12)
O4'—C12—C11112.1 (3)C10—N1—C8120.70 (13)
O4—C12—C11111.89 (19)C11—N1—C8122.09 (12)
O4—C13—C14114.1 (6)C9—N2—C11113.13 (12)
O4—C13—H13A108.7C9—N2—C7122.32 (13)
C14—C13—H13A108.7C11—N2—C7121.95 (12)
O4—C13—H13B108.7C10—N3—C15111.23 (12)
C14—C13—H13B108.7C10—N3—C19120.06 (13)
H13A—C13—H13B107.6C15—N3—C19116.63 (12)
C12—O4—C13117.0 (3)C9—N4—C15110.04 (11)
O4'—C13'—C14'111.7 (11)C9—N4—C20118.89 (13)
O4'—C13'—H13C109.3C15—N4—C20116.33 (12)
C14'—C13'—H13C109.3C16—O6—C17119.81 (18)
O4'—C13'—H13D109.3C19—O7—C20111.00 (12)
C14'—C13'—H13D109.3
C6—C1—C2—C30.3 (2)O2—C10—N1—C815.6 (2)
C8—C1—C2—C3179.16 (15)N3—C10—N1—C8168.33 (12)
C1—C2—C3—C40.2 (3)N2—C11—N1—C10101.08 (14)
C2—C3—C4—C50.4 (3)C12—C11—N1—C10134.09 (14)
C3—C4—C5—C60.2 (3)C15—C11—N1—C108.90 (15)
C4—C5—C6—C10.3 (2)N2—C11—N1—C854.73 (17)
C4—C5—C6—C7179.31 (15)C12—C11—N1—C870.11 (17)
C2—C1—C6—C50.6 (2)C15—C11—N1—C8164.71 (13)
C8—C1—C6—C5178.91 (14)C1—C8—N1—C1079.25 (17)
C2—C1—C6—C7179.04 (13)C1—C8—N1—C1174.62 (18)
C8—C1—C6—C71.5 (2)O1—C9—N2—C11170.93 (14)
C5—C6—C7—N2120.34 (15)N4—C9—N2—C1112.05 (17)
C1—C6—C7—N259.29 (18)O1—C9—N2—C78.9 (2)
C2—C1—C8—N1120.13 (15)N4—C9—N2—C7174.08 (12)
C6—C1—C8—N160.38 (19)N1—C11—N2—C9104.61 (14)
N2—C11—C12—O325.0 (2)C12—C11—N2—C9128.42 (14)
N1—C11—C12—O3152.36 (19)C15—C11—N2—C95.85 (16)
C15—C11—C12—O389.4 (2)N1—C11—N2—C757.49 (17)
N2—C11—C12—O4'133.4 (5)C12—C11—N2—C769.48 (17)
N1—C11—C12—O4'6.1 (5)C15—C11—N2—C7167.95 (12)
C15—C11—C12—O4'112.2 (5)C6—C7—N2—C982.07 (17)
N2—C11—C12—O4163.0 (3)C6—C7—N2—C1178.39 (17)
N1—C11—C12—O435.7 (3)O2—C10—N3—C15173.69 (14)
C15—C11—C12—O482.6 (3)N1—C10—N3—C1510.20 (16)
O3—C12—O4—C132.9 (7)O2—C10—N3—C1932.4 (2)
O4'—C12—O4—C1395.3 (10)N1—C10—N3—C19151.49 (13)
C11—C12—O4—C13168.7 (4)N4—C15—N3—C10107.58 (14)
C14—C13—O4—C1285.3 (5)C16—C15—N3—C10128.36 (14)
O3—C12—O4'—C13'18.3 (11)C11—C15—N3—C104.50 (15)
O4—C12—O4'—C13'87.8 (11)N4—C15—N3—C1935.16 (18)
C11—C12—O4'—C13'176.9 (6)C16—C15—N3—C1988.91 (16)
C14'—C13'—O4'—C1266.9 (11)C11—C15—N3—C19147.23 (13)
N2—C11—C15—N42.19 (14)O7—C19—N3—C1092.35 (16)
N1—C11—C15—N4120.37 (12)O7—C19—N3—C1546.95 (19)
C12—C11—C15—N4115.96 (13)O1—C9—N4—C15169.69 (14)
N2—C11—C15—N3115.74 (12)N2—C9—N4—C1513.28 (16)
N1—C11—C15—N32.45 (14)O1—C9—N4—C2031.9 (2)
C12—C11—C15—N3126.11 (12)N2—C9—N4—C20151.06 (13)
N2—C11—C15—C16124.56 (14)N3—C15—N4—C9102.28 (14)
N1—C11—C15—C16117.25 (14)C16—C15—N4—C9134.58 (13)
C12—C11—C15—C166.41 (18)C11—C15—N4—C99.29 (15)
N4—C15—C16—O5149.1 (9)N3—C15—N4—C2036.69 (18)
N3—C15—C16—O586.0 (9)C16—C15—N4—C2086.44 (16)
C11—C15—C16—O530.4 (9)C11—C15—N4—C20148.26 (12)
N4—C15—C16—O5'92.3 (9)O7—C20—N4—C985.57 (16)
N3—C15—C16—O5'142.8 (9)O7—C20—N4—C1549.66 (18)
C11—C15—C16—O5'26.4 (9)O5—C16—O6—C1730.9 (11)
N4—C15—C16—O661.6 (2)O5'—C16—O6—C1725.0 (10)
N3—C15—C16—O663.3 (2)C15—C16—O6—C17179.75 (19)
C11—C15—C16—O6179.72 (15)C18—C17—O6—C16165.9 (2)
O2—C10—N1—C11171.78 (14)N3—C19—O7—C2059.05 (17)
N3—C10—N1—C1112.14 (16)N4—C20—O7—C1960.30 (16)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C17—H17B···O2i0.972.513.373 (3)148
C19—H19B···O1ii0.972.553.457 (2)156
C20—H20A···O2ii0.972.473.217 (2)133
Symmetry codes: (i) x1, y, z; (ii) x+1, y+2, z+1.
 

Follow Acta Cryst. E
Sign up for e-alerts
Follow Acta Cryst. on Twitter
Follow us on facebook
Sign up for RSS feeds