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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
CCDC reference: 610685
Key indicators
- Single-crystal X-ray study
- T = 292 K
- Mean (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
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,3
H,4H,11
H-2-oxa-3a,4a,10
a,11
a-
tetraazazbenz[
f]indeno[2,1,7-ija]azulene-11
b,11
c-dicarboxylate
top
Crystal data top
C20H21IN4O7 | F(000) = 2224 |
Mr = 556.31 | Dx = 1.736 Mg m−3 |
Orthorhombic, Pbca | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ac 2ab | Cell parameters from 4829 reflections |
a = 15.533 (6) Å | θ = 2.4–19.7° |
b = 11.414 (5) Å | µ = 1.56 mm−1 |
c = 24.006 (10) Å | T = 292 K |
V = 4256 (3) Å3 | Block, colorless |
Z = 8 | 0.10 × 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 tube | Rint = 0.134 |
Graphite monochromator | θmax = 27.5°, θmin = 1.7° |
φ and ω scans | h = −20→20 |
46045 measured reflections | k = −14→14 |
4856 independent reflections | l = −31→31 |
Refinement top
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.059 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.148 | H-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 parameters | Δρmax = 0.97 e Å−3 |
2 restraints | Δρmin = −0.92 e Å−3 |
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 | x | y | z | Uiso*/Ueq | Occ. (<1) |
C1 | 0.1317 (3) | 0.6780 (4) | 1.0936 (2) | 0.0352 (11) | |
C2 | 0.1706 (4) | 0.7379 (5) | 1.1377 (2) | 0.0514 (15) | |
H2 | 0.1549 | 0.7215 | 1.1743 | 0.062* | |
C3 | 0.2314 (4) | 0.8198 (6) | 1.1269 (2) | 0.0584 (17) | |
H3 | 0.2574 | 0.8599 | 1.1561 | 0.070* | |
C4 | 0.2551 (3) | 0.8444 (5) | 1.0722 (2) | 0.0470 (13) | |
H4 | 0.2963 | 0.9017 | 1.0652 | 0.056* | |
C5 | 0.2181 (3) | 0.7849 (4) | 1.02803 (19) | 0.0290 (10) | |
C6 | 0.1542 (3) | 0.6992 (4) | 1.03898 (18) | 0.0282 (10) | |
C7 | 0.1162 (3) | 0.6302 (4) | 0.98996 (17) | 0.0274 (10) | |
H7A | 0.1624 | 0.5881 | 0.9716 | 0.033* | |
H7B | 0.0763 | 0.5725 | 1.0045 | 0.033* | |
C8 | 0.2459 (3) | 0.8138 (4) | 0.9703 (2) | 0.0326 (11) | |
H8A | 0.2895 | 0.8746 | 0.9722 | 0.039* | |
H8B | 0.2725 | 0.7449 | 0.9541 | 0.039* | |
C9 | −0.0100 (3) | 0.7451 (4) | 0.95908 (18) | 0.0266 (10) | |
C10 | 0.1498 (3) | 0.9652 (4) | 0.93250 (19) | 0.0283 (10) | |
C11 | 0.1183 (3) | 0.7711 (4) | 0.90862 (17) | 0.0244 (9) | |
C12 | 0.1670 (3) | 0.6994 (4) | 0.8643 (2) | 0.0328 (11) | |
C13 | 0.2020 (4) | 0.5120 (5) | 0.8299 (2) | 0.0457 (13) | |
H13A | 0.1979 | 0.4321 | 0.8434 | 0.055* | |
H13B | 0.2617 | 0.5361 | 0.8324 | 0.055* | |
C14 | 0.1739 (4) | 0.5161 (6) | 0.7703 (2) | 0.0635 (18) | |
H14A | 0.1146 | 0.4933 | 0.7677 | 0.095* | |
H14B | 0.2086 | 0.4632 | 0.7487 | 0.095* | |
H14C | 0.1807 | 0.5943 | 0.7562 | 0.095* | |
C15 | 0.0478 (3) | 0.8542 (4) | 0.88474 (18) | 0.0286 (10) | |
C16 | 0.0284 (3) | 0.8433 (5) | 0.8222 (2) | 0.0418 (12) | |
C17 | −0.0194 (4) | 0.7153 (6) | 0.7512 (2) | 0.0608 (17) | |
H17A | −0.0076 | 0.7835 | 0.7283 | 0.073* | |
H17B | 0.0161 | 0.6513 | 0.7377 | 0.073* | |
C18 | −0.1074 (4) | 0.6844 (7) | 0.7459 (3) | 0.082 (2) | |
H18A | −0.1193 | 0.6174 | 0.7688 | 0.123* | |
H18B | −0.1198 | 0.6660 | 0.7078 | 0.123* | |
H18C | −0.1426 | 0.7489 | 0.7577 | 0.123* | |
C19 | −0.0916 (3) | 0.9155 (4) | 0.9240 (2) | 0.0371 (12) | |
H19A | −0.1195 | 0.9326 | 0.8888 | 0.044* | |
H19B | −0.1354 | 0.8896 | 0.9501 | 0.044* | |
C20 | 0.0122 (4) | 1.0592 (4) | 0.9075 (3) | 0.0449 (13) | |
H20A | 0.0388 | 1.1293 | 0.9226 | 0.054* | |
H20B | −0.0146 | 1.0798 | 0.8724 | 0.054* | |
I1 | 0.03876 (3) | 0.55284 (4) | 1.115638 (16) | 0.05707 (18) | |
N1 | 0.0717 (2) | 0.7007 (3) | 0.94882 (14) | 0.0227 (8) | |
N2 | 0.1777 (2) | 0.8530 (3) | 0.93373 (15) | 0.0259 (8) | |
N3 | −0.0293 (2) | 0.8235 (3) | 0.91626 (15) | 0.0265 (8) | |
N4 | 0.0782 (2) | 0.9709 (3) | 0.89786 (15) | 0.0288 (8) | |
O1 | −0.05713 (19) | 0.7168 (3) | 0.99608 (14) | 0.0371 (8) | |
O2 | 0.18354 (19) | 1.0479 (2) | 0.95556 (14) | 0.0354 (8) | |
O3 | 0.1493 (2) | 0.5883 (3) | 0.86506 (14) | 0.0346 (8) | |
O4 | 0.2156 (3) | 0.7454 (3) | 0.83333 (19) | 0.0789 (15) | |
O5 | 0.0257 (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) |
O6 | 0.0030 (3) | 0.7408 (4) | 0.80865 (15) | 0.0592 (11) | |
O7 | −0.0516 (2) | 1.0192 (3) | 0.94482 (16) | 0.0423 (9) | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
C1 | 0.031 (3) | 0.034 (3) | 0.041 (3) | 0.001 (2) | −0.001 (2) | −0.003 (2) |
C2 | 0.049 (3) | 0.069 (4) | 0.036 (3) | 0.003 (3) | 0.001 (3) | −0.014 (3) |
C3 | 0.051 (4) | 0.081 (5) | 0.043 (3) | −0.005 (3) | −0.013 (3) | −0.025 (3) |
C4 | 0.034 (3) | 0.044 (3) | 0.063 (4) | −0.004 (2) | −0.007 (3) | −0.011 (3) |
C5 | 0.022 (2) | 0.026 (2) | 0.039 (3) | 0.0061 (18) | −0.004 (2) | −0.0040 (19) |
C6 | 0.024 (2) | 0.024 (2) | 0.036 (3) | 0.0095 (19) | −0.0014 (19) | −0.0022 (19) |
C7 | 0.027 (2) | 0.022 (2) | 0.033 (2) | 0.0010 (18) | 0.0066 (19) | 0.0016 (18) |
C8 | 0.023 (2) | 0.020 (2) | 0.055 (3) | 0.0009 (18) | −0.001 (2) | −0.003 (2) |
C9 | 0.023 (2) | 0.028 (2) | 0.028 (3) | −0.0054 (19) | −0.0007 (19) | −0.0069 (19) |
C10 | 0.025 (2) | 0.022 (2) | 0.038 (3) | −0.0006 (19) | 0.010 (2) | 0.0010 (19) |
C11 | 0.028 (2) | 0.019 (2) | 0.026 (2) | −0.0046 (18) | 0.0044 (18) | −0.0026 (17) |
C12 | 0.032 (3) | 0.025 (2) | 0.042 (3) | −0.002 (2) | 0.006 (2) | −0.009 (2) |
C13 | 0.056 (4) | 0.032 (3) | 0.049 (3) | 0.016 (3) | 0.009 (3) | −0.011 (2) |
C14 | 0.078 (5) | 0.059 (4) | 0.054 (4) | 0.013 (3) | −0.002 (3) | −0.025 (3) |
C15 | 0.024 (2) | 0.028 (2) | 0.034 (2) | −0.0011 (18) | 0.003 (2) | 0.001 (2) |
C16 | 0.050 (3) | 0.042 (3) | 0.034 (3) | −0.009 (3) | −0.004 (2) | −0.001 (2) |
C17 | 0.070 (4) | 0.078 (5) | 0.034 (3) | −0.005 (4) | −0.007 (3) | −0.020 (3) |
C18 | 0.069 (5) | 0.102 (6) | 0.075 (5) | −0.008 (4) | −0.022 (4) | −0.013 (4) |
C19 | 0.021 (2) | 0.039 (3) | 0.051 (3) | 0.005 (2) | −0.004 (2) | 0.000 (2) |
C20 | 0.041 (3) | 0.031 (3) | 0.063 (4) | 0.011 (2) | −0.007 (3) | 0.001 (3) |
I1 | 0.0702 (3) | 0.0542 (3) | 0.0468 (3) | −0.01104 (19) | 0.01784 (19) | 0.00370 (18) |
N1 | 0.0233 (18) | 0.0168 (18) | 0.0281 (19) | −0.0018 (15) | 0.0048 (15) | −0.0001 (14) |
N2 | 0.0207 (18) | 0.0171 (18) | 0.040 (2) | −0.0018 (15) | 0.0008 (15) | −0.0043 (16) |
N3 | 0.0181 (18) | 0.032 (2) | 0.030 (2) | −0.0010 (16) | 0.0014 (15) | 0.0004 (16) |
N4 | 0.028 (2) | 0.0202 (19) | 0.038 (2) | −0.0022 (16) | −0.0005 (17) | 0.0009 (15) |
O1 | 0.0260 (18) | 0.043 (2) | 0.043 (2) | −0.0016 (15) | 0.0094 (15) | 0.0043 (16) |
O2 | 0.0319 (18) | 0.0226 (17) | 0.052 (2) | −0.0043 (14) | −0.0009 (15) | −0.0110 (15) |
O3 | 0.0393 (19) | 0.0212 (16) | 0.0433 (19) | −0.0018 (14) | 0.0112 (16) | −0.0073 (14) |
O4 | 0.092 (3) | 0.046 (2) | 0.099 (4) | −0.032 (2) | 0.067 (3) | −0.031 (2) |
O5 | 0.157 (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) |
O6 | 0.083 (3) | 0.059 (3) | 0.035 (2) | −0.022 (2) | −0.009 (2) | −0.0035 (19) |
O7 | 0.034 (2) | 0.037 (2) | 0.056 (2) | 0.0098 (15) | 0.0013 (17) | −0.0056 (17) |
Geometric parameters (Å, º) top
C1—C6 | 1.378 (6) | C12—O3 | 1.297 (5) |
C1—C2 | 1.399 (7) | C13—O3 | 1.463 (5) |
C1—I1 | 2.099 (5) | C13—C14 | 1.496 (7) |
C2—C3 | 1.354 (8) | C13—H13A | 0.9700 |
C2—H2 | 0.9300 | C13—H13B | 0.9700 |
C3—C4 | 1.392 (8) | C14—H14A | 0.9600 |
C3—H3 | 0.9300 | C14—H14B | 0.9600 |
C4—C5 | 1.384 (6) | C14—H14C | 0.9600 |
C4—H4 | 0.9300 | C15—N4 | 1.448 (6) |
C5—C6 | 1.418 (6) | C15—N3 | 1.459 (5) |
C5—C8 | 1.488 (6) | C15—C16 | 1.537 (6) |
C6—C7 | 1.534 (6) | C16—O5 | 1.203 (7) |
C7—N1 | 1.449 (5) | C16—O6 | 1.276 (6) |
C7—H7A | 0.9700 | C16—O5' | 1.30 (2) |
C7—H7B | 0.9700 | C17—C18 | 1.417 (8) |
C8—N2 | 1.448 (5) | C17—O6 | 1.452 (6) |
C8—H8A | 0.9700 | C17—H17A | 0.9700 |
C8—H8B | 0.9700 | C17—H17B | 0.9700 |
C9—O1 | 1.196 (5) | C18—H18A | 0.9600 |
C9—N1 | 1.389 (5) | C18—H18B | 0.9600 |
C9—N3 | 1.395 (6) | C18—H18C | 0.9600 |
C10—O2 | 1.214 (5) | C19—O7 | 1.427 (6) |
C10—N2 | 1.352 (5) | C19—N3 | 1.440 (6) |
C10—N4 | 1.390 (6) | C19—H19A | 0.9700 |
C11—N2 | 1.445 (5) | C19—H19B | 0.9700 |
C11—N1 | 1.449 (5) | C20—O7 | 1.411 (7) |
C11—C12 | 1.541 (6) | C20—N4 | 1.457 (6) |
C11—C15 | 1.558 (6) | C20—H20A | 0.9700 |
C12—O4 | 1.182 (6) | C20—H20B | 0.9700 |
| | | |
C6—C1—C2 | 121.7 (5) | C13—C14—H14C | 109.5 |
C6—C1—I1 | 122.3 (3) | H14A—C14—H14C | 109.5 |
C2—C1—I1 | 116.0 (4) | H14B—C14—H14C | 109.5 |
C3—C2—C1 | 119.5 (5) | N4—C15—N3 | 112.1 (4) |
C3—C2—H2 | 120.2 | N4—C15—C16 | 110.6 (4) |
C1—C2—H2 | 120.2 | N3—C15—C16 | 109.0 (4) |
C2—C3—C4 | 120.4 (5) | N4—C15—C11 | 104.5 (3) |
C2—C3—H3 | 119.8 | N3—C15—C11 | 103.9 (3) |
C4—C3—H3 | 119.8 | C16—C15—C11 | 116.6 (4) |
C5—C4—C3 | 120.9 (5) | O5—C16—O6 | 123.4 (5) |
C5—C4—H4 | 119.6 | O5—C16—O5' | 58.2 (17) |
C3—C4—H4 | 119.6 | O6—C16—O5' | 108.4 (17) |
C4—C5—C6 | 119.2 (4) | O5—C16—C15 | 123.2 (5) |
C4—C5—C8 | 118.9 (4) | O6—C16—C15 | 112.6 (4) |
C6—C5—C8 | 121.9 (4) | O5'—C16—C15 | 113.5 (11) |
C1—C6—C5 | 118.3 (4) | C18—C17—O6 | 111.4 (5) |
C1—C6—C7 | 122.8 (4) | C18—C17—H17A | 109.3 |
C5—C6—C7 | 118.8 (4) | O6—C17—H17A | 109.3 |
N1—C7—C6 | 114.9 (3) | C18—C17—H17B | 109.3 |
N1—C7—H7A | 108.5 | O6—C17—H17B | 109.3 |
C6—C7—H7A | 108.5 | H17A—C17—H17B | 108.0 |
N1—C7—H7B | 108.5 | C17—C18—H18A | 109.5 |
C6—C7—H7B | 108.5 | C17—C18—H18B | 109.5 |
H7A—C7—H7B | 107.5 | H18A—C18—H18B | 109.5 |
N2—C8—C5 | 114.8 (4) | C17—C18—H18C | 109.5 |
N2—C8—H8A | 108.6 | H18A—C18—H18C | 109.5 |
C5—C8—H8A | 108.6 | H18B—C18—H18C | 109.5 |
N2—C8—H8B | 108.6 | O7—C19—N3 | 111.0 (3) |
C5—C8—H8B | 108.6 | O7—C19—H19A | 109.4 |
H8A—C8—H8B | 107.5 | N3—C19—H19A | 109.4 |
O1—C9—N1 | 126.3 (4) | O7—C19—H19B | 109.4 |
O1—C9—N3 | 126.1 (4) | N3—C19—H19B | 109.4 |
N1—C9—N3 | 107.5 (4) | H19A—C19—H19B | 108.0 |
O2—C10—N2 | 126.0 (4) | O7—C20—N4 | 111.8 (4) |
O2—C10—N4 | 125.6 (4) | O7—C20—H20A | 109.3 |
N2—C10—N4 | 108.3 (4) | N4—C20—H20A | 109.3 |
N2—C11—N1 | 113.5 (3) | O7—C20—H20B | 109.3 |
N2—C11—C12 | 108.5 (3) | N4—C20—H20B | 109.3 |
N1—C11—C12 | 114.2 (3) | H20A—C20—H20B | 107.9 |
N2—C11—C15 | 102.1 (3) | C9—N1—C7 | 121.2 (3) |
N1—C11—C15 | 103.4 (3) | C9—N1—C11 | 111.8 (3) |
C12—C11—C15 | 114.5 (4) | C7—N1—C11 | 121.6 (3) |
O4—C12—O3 | 125.3 (4) | C10—N2—C11 | 113.5 (4) |
O4—C12—C11 | 120.7 (4) | C10—N2—C8 | 122.7 (4) |
O3—C12—C11 | 113.9 (4) | C11—N2—C8 | 121.4 (3) |
O3—C13—C14 | 111.8 (4) | C9—N3—C19 | 121.1 (4) |
O3—C13—H13A | 109.3 | C9—N3—C15 | 111.1 (3) |
C14—C13—H13A | 109.3 | C19—N3—C15 | 116.3 (4) |
O3—C13—H13B | 109.3 | C10—N4—C15 | 110.4 (3) |
C14—C13—H13B | 109.3 | C10—N4—C20 | 120.0 (4) |
H13A—C13—H13B | 107.9 | C15—N4—C20 | 116.2 (4) |
C13—C14—H14A | 109.5 | C12—O3—C13 | 117.1 (4) |
C13—C14—H14B | 109.5 | C16—O6—C17 | 120.0 (5) |
H14A—C14—H14B | 109.5 | C20—O7—C19 | 110.6 (4) |
| | | |
C6—C1—C2—C3 | 0.7 (8) | C15—C11—N1—C9 | −11.3 (4) |
I1—C1—C2—C3 | 179.9 (4) | N2—C11—N1—C7 | −55.8 (5) |
C1—C2—C3—C4 | 0.0 (9) | C12—C11—N1—C7 | 69.4 (5) |
C2—C3—C4—C5 | −0.9 (9) | C15—C11—N1—C7 | −165.5 (3) |
C3—C4—C5—C6 | 1.1 (7) | O2—C10—N2—C11 | 172.2 (4) |
C3—C4—C5—C8 | −179.6 (5) | N4—C10—N2—C11 | −10.9 (5) |
C2—C1—C6—C5 | −0.5 (7) | O2—C10—N2—C8 | 9.6 (7) |
I1—C1—C6—C5 | −179.6 (3) | N4—C10—N2—C8 | −173.5 (4) |
C2—C1—C6—C7 | 176.6 (4) | N1—C11—N2—C10 | −105.3 (4) |
I1—C1—C6—C7 | −2.6 (6) | C12—C11—N2—C10 | 126.6 (4) |
C4—C5—C6—C1 | −0.4 (6) | C15—C11—N2—C10 | 5.4 (4) |
C8—C5—C6—C1 | −179.7 (4) | N1—C11—N2—C8 | 57.7 (5) |
C4—C5—C6—C7 | −177.6 (4) | C12—C11—N2—C8 | −70.5 (5) |
C8—C5—C6—C7 | 3.1 (6) | C15—C11—N2—C8 | 168.3 (3) |
C1—C6—C7—N1 | 121.4 (4) | C5—C8—N2—C10 | 83.3 (5) |
C5—C6—C7—N1 | −61.6 (5) | C5—C8—N2—C11 | −78.1 (5) |
C4—C5—C8—N2 | −121.4 (4) | O1—C9—N3—C19 | 27.3 (7) |
C6—C5—C8—N2 | 57.9 (5) | N1—C9—N3—C19 | −156.4 (4) |
N2—C11—C12—O4 | −43.1 (6) | O1—C9—N3—C15 | 169.3 (4) |
N1—C11—C12—O4 | −170.8 (5) | N1—C9—N3—C15 | −14.4 (5) |
C15—C11—C12—O4 | 70.2 (6) | O7—C19—N3—C9 | 89.7 (5) |
N2—C11—C12—O3 | 136.8 (4) | O7—C19—N3—C15 | −50.4 (5) |
N1—C11—C12—O3 | 9.1 (6) | N4—C15—N3—C9 | −105.0 (4) |
C15—C11—C12—O3 | −109.9 (4) | C16—C15—N3—C9 | 132.2 (4) |
N2—C11—C15—N4 | 1.9 (4) | C11—C15—N3—C9 | 7.2 (4) |
N1—C11—C15—N4 | 119.9 (3) | N4—C15—N3—C19 | 38.9 (5) |
C12—C11—C15—N4 | −115.2 (4) | C16—C15—N3—C19 | −83.8 (5) |
N2—C11—C15—N3 | −115.8 (3) | C11—C15—N3—C19 | 151.1 (4) |
N1—C11—C15—N3 | 2.3 (4) | O2—C10—N4—C15 | −171.2 (4) |
C12—C11—C15—N3 | 127.2 (4) | N2—C10—N4—C15 | 11.9 (5) |
N2—C11—C15—C16 | 124.2 (4) | O2—C10—N4—C20 | −31.9 (7) |
N1—C11—C15—C16 | −117.7 (4) | N2—C10—N4—C20 | 151.2 (4) |
C12—C11—C15—C16 | 7.2 (5) | N3—C15—N4—C10 | 103.6 (4) |
N4—C15—C16—O5 | −11.2 (11) | C16—C15—N4—C10 | −134.5 (4) |
N3—C15—C16—O5 | 112.5 (10) | C11—C15—N4—C10 | −8.3 (4) |
C11—C15—C16—O5 | −130.3 (10) | N3—C15—N4—C20 | −37.4 (5) |
N4—C15—C16—O6 | 178.7 (4) | C16—C15—N4—C20 | 84.4 (5) |
N3—C15—C16—O6 | −57.7 (6) | C11—C15—N4—C20 | −149.3 (4) |
C11—C15—C16—O6 | 59.5 (6) | O7—C20—N4—C10 | −88.7 (5) |
N4—C15—C16—O5' | 55 (2) | O7—C20—N4—C15 | 48.4 (6) |
N3—C15—C16—O5' | 179 (2) | O4—C12—O3—C13 | 8.5 (8) |
C11—C15—C16—O5' | −64 (2) | C11—C12—O3—C13 | −171.4 (4) |
O1—C9—N1—C7 | −13.1 (6) | C14—C13—O3—C12 | −79.5 (6) |
N3—C9—N1—C7 | 170.6 (3) | O5—C16—O6—C17 | 9.0 (12) |
O1—C9—N1—C11 | −167.5 (4) | O5'—C16—O6—C17 | −55 (2) |
N3—C9—N1—C11 | 16.2 (4) | C15—C16—O6—C17 | 179.2 (4) |
C6—C7—N1—C9 | −75.8 (5) | C18—C17—O6—C16 | −117.0 (7) |
C6—C7—N1—C11 | 76.0 (5) | N4—C20—O7—C19 | −58.5 (5) |
N2—C11—N1—C9 | 98.5 (4) | N3—C19—O7—C20 | 59.4 (5) |
C12—C11—N1—C9 | −136.4 (4) | | |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C19—H19B···O2i | 0.97 | 2.49 | 3.251 (6) | 135 |
C13—H13A···O4ii | 0.97 | 2.53 | 3.302 (6) | 136 |
C8—H8B···O2ii | 0.97 | 2.35 | 3.246 (5) | 153 |
C7—H7A···O2ii | 0.97 | 2.47 | 3.353 (5) | 152 |
Symmetry codes: (i) −x, −y+2, −z+2; (ii) −x+1/2, y−1/2, z. |
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