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The title compound, C26H22N4O5 (systematic name: methyl 2-eth­oxy-1-{4-[2-(5-oxo-4,5-di­hydro-1,2,4-oxa­diazol-3-yl)phenyl]benz­yl}-1H-1,3-benzo­diazole-7-carboxyl­ate ethyl acetate hemisolvate), was obtained via cyclization of methyl (Z)-2-eth­oxy-1-{(2′-(N′-hy­droxy­carbamimido­yl)-[1,1′-biphen­yl]-4-yl)meth­yl}-1H-benzo[d]imidazole-7-carboxyl­ate with diphen­yl carbonate. There are two independent mol­ecules (A and B) with different conformations and an ethyl acetate solvent mol­ecule in the asymmetric unit. In mol­ecule A, the dihedral angle between the benzene ring and its attached oxa­diazole ring is 59.36 (17); the dihedral angle between the benzene rings is 43.89 (15) and that between the benzene ring and its attached imidazole ring system is 80.06 (11)°. The corres­ponding dihedral angles in mol­ecule B are 58.45 (18), 50.73 (16) and 85.37 (10)°, respectively. The C—O—C—Cm (m = meth­yl) torsion angles for the eth­oxy side chains attached to the imidazole rings in mol­ecules A and B are 93.9 (3) and −174.6 (3)°, respectively. In the crystal, the components are linked by N—H...N and C—H...O hydrogen bonds, generating a three-dimensional network. Aromatic π–π stacking inter­actions [shortest centroid–centroid separation = 3.536 (3)Å] are also observed.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S2056989014028023/hb7346sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2056989014028023/hb7346Isup2.hkl
Contains datablock I

cml

Chemical Markup Language (CML) file https://doi.org/10.1107/S2056989014028023/hb7346Isup3.cml
Supplementary material

CCDC reference: 934880

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.005 Å
  • R factor = 0.064
  • wR factor = 0.221
  • Data-to-parameter ratio = 12.9

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT094_ALERT_2_C Ratio of Maximum / Minimum Residual Density .... 2.01 Report PLAT242_ALERT_2_C Low Ueq as Compared to Neighbors for ..... C2 Check PLAT243_ALERT_4_C High 'Solvent' Ueq as Compared to Neighbors of C54 Check PLAT244_ALERT_4_C Low 'Solvent' Ueq as Compared to Neighbors of C55 Check PLAT340_ALERT_3_C Low Bond Precision on C-C Bonds ............... 0.0046 Ang. PLAT360_ALERT_2_C Short C(sp3)-C(sp3) Bond C53 - C54 ... 1.40 Ang. PLAT745_ALERT_1_C D-H Calc 0.99(4), Rep 1.01000 ...... Missing su N5 -H5A 1.555 1.555 # 135 PLAT745_ALERT_1_C D-H Calc 0.90(5), Rep 0.90000 ...... Missing su N7 -H7 1.555 1.555 # 135 PLAT746_ALERT_1_C H...A Calc 1.88(4), Rep 1.85000 ...... Missing su H5A -N4 1.555 2.566 # 135 PLAT746_ALERT_1_C H...A Calc 2.01(5), Rep 2.01000 ...... Missing su H7 -N2 1.555 2.566 # 135 PLAT906_ALERT_3_C Large K value in the Analysis of Variance ...... 6.221 Check PLAT911_ALERT_3_C Missing # FCF Refl Between THmin & STh/L= 0.595 140 Report PLAT913_ALERT_3_C Missing # of Very Strong Reflections in FCF .... 40 Note PLAT918_ALERT_3_C Reflection(s) with I(obs) much smaller I(calc) . 4 Check PLAT939_ALERT_3_C Large Value of Not (SHELXL) Weight Optimized S . 10.03
Alert level G PLAT005_ALERT_5_G No _iucr_refine_instructions_details in the CIF Please Do ! PLAT042_ALERT_1_G Calc. and Reported MoietyFormula Strings Differ Please Check PLAT045_ALERT_1_G Calculated and Reported Z Differ by ............ 0.50 Ratio PLAT066_ALERT_1_G Predicted and Reported Tmin&Tmax Range Identical ? Check PLAT072_ALERT_2_G SHELXL First Parameter in WGHT Unusually Large. 0.16 Report PLAT199_ALERT_1_G Reported _cell_measurement_temperature ..... (K) 293 Check PLAT200_ALERT_1_G Reported _diffrn_ambient_temperature ..... (K) 293 Check PLAT899_ALERT_4_G SHELXL97 is Deprecated and Succeeded by SHELXL 2014 Note PLAT909_ALERT_3_G Percentage of Observed Data at Theta(Max) still 40 % PLAT961_ALERT_5_G Dataset Contains no Negative Intensities ....... Please Check
0 ALERT level A = Most likely a serious problem - resolve or explain 0 ALERT level B = A potentially serious problem, consider carefully 15 ALERT level C = Check. Ensure it is not caused by an omission or oversight 10 ALERT level G = General information/check it is not something unexpected 9 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 7 ALERT type 3 Indicator that the structure quality may be low 3 ALERT type 4 Improvement, methodology, query or suggestion 2 ALERT type 5 Informative message, check

Comment top

Azilsartan (TAK-536) as an angiotensin II type 1 (AT1) receptor blocker (ARB) has perfect antihypertensive effect (Ojima et al., 2011; Michel et al., 2013; Weltman et al., 2012). Azilsartan methyl ester, as the key synthetic intermediate of azilsartan has being paid widely attention. Although the synthesis of azilsartan methyl ester has been descripted in many literatures (Kohara et al., 1996; Rádl et al., 2013), there was no particular work on the structural characterization involving crystal structure. We herein present the crystal structure of methyl 2-ethoxy-1-((2'-(5-oxo-4,5-dihydro-1,2,4-oxadiazol-3-yl) -[1,1'-biphenyl]-4-yl)methyl)-1H-benzo[d]imidazole-7- carboxylate (I).

In the molecular structure (Fig. 1), there are two independent title molecules with different conformations and an ethyl acetate solvent molecule to form the minimum repeat unit of the crystal. The dihedral angles between the two phenyl rings (C38–C43 with C44–C49; C13–C18 with C19–C24) of phenylbenzenes are 50.7 (2)° and 43.9 (1)°, respectively. The new constructed 5-oxo-1,2,4-oxadiazole heterocycle (N5–C26–O4–N6–C25 or N7–C51–O10–N8–C50) adopts a planer structure. In the packing structure (Fig. 2), the two different title compound molecules formed a dimer through two intermolecular N–H···N hydrogen bond (N5–H5A···N4 and N7–H7···N2) between the imidazole rings and 5-oxo-1,2,4-oxadiazole rings. Then intermolecular ππ stacking (Cg1···Cg2i, 3.62 (2) Å, symmetry codes: (i), -x, 1 - y, 1 - z. Cg1 and Cg2 are the centroids of the N3–C33–C32–N4–C34 and C28–C33 rings, respectively) between the two benzo[d]imidazole rings and C–H···O weak interactions (C12–H12A···O5 and C30–H30···O9) link the adjacent dimers.

Related literature top

For general background to azilsartan, an angiotensin II type 1 (AT1) receptor blocker (ARB) having a perfect antihypertensive effect, see: Michel et al. (2013); Weltman et al. (2012); Ojima et al. (2011). For the synthesis of azilsartan methyl ester, the key synthetic intermediate of azilsartan, see: Kohara et al. (1996); Rádl et al. (2013).

Experimental top

A mixture of methyl (Z)-2-ethoxy-1-((2'-(N'-hydroxycarbamimidoyl) -[1,1'-biphenyl]-4-yl)methyl)-1H-benzo[d]imidazole-7-carboxylate (6 g, 13.5 mmol), diphenyl carbonate (4.34 g, 20.25 mmol) and K2CO3 (2.8 g, 20.25 mmol) in DMSO (150 ml) was stirred at room temperature for 5 h. After the reaction, the mixture was poured into water (400 ml) and the insoluble portion was filtered off. The aqueous solution was acidified with 1 N HCl to PH = 3–4, and the formed precipitate was filtered off, washed with sodium carbonate solution, and dried in vacuo to afford a white solid (5.28 g, 83% yield, m.p. 468–470 K). Colourless blocks were obtained by slow evaporation of an ethyl acetate solution at room temperature.

Refinement top

All the H bonded to C atoms were placed in geometrically idealized positions and constrained to ride on their parent atoms, with C—H distances of 0.93–0.97 Å, and with Uiso(H) = 1.2–1.5Ueq(C). All the H on N atoms were located in a differences Fourier map and refined isotropically.

Computing details top

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. The molecular structure of the title compound. Displacement ellipsoids are drawn at the 30% probability level. All H atoms have been omitted for clarity.
[Figure 2] Fig. 2. Crystal packing of (I). Hydrogen bonds are shown as dashed lines.
Methyl 2-ethoxy-1-{4-[2-(5-oxo-4,5-dihydro-1,2,4-oxadiazol-3-yl)phenyl]benzyl}-1H-1,3-benzodiazole-7-carboxylate ethyl acetate hemisolvate top
Crystal data top
C26H22N4O5·0.5C4H8O2Z = 4
Mr = 514.53F(000) = 1080
Triclinic, P1Dx = 1.314 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 13.662 (5) ÅCell parameters from 5677 reflections
b = 14.928 (6) Åθ = 2.4–28.3°
c = 15.356 (10) ŵ = 0.09 mm1
α = 95.459 (11)°T = 293 K
β = 106.226 (11)°BLOCK, colorless
γ = 116.524 (8)°0.25 × 0.20 × 0.18 mm
V = 2601 (2) Å3
Data collection top
Bruker APEXII CCD
diffractometer
9024 independent reflections
Radiation source: fine-focus sealed tube6365 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.030
phi and ω scansθmax = 25.0°, θmin = 1.4°
Absorption correction: multi-scan
(SADABS; Bruker, 2009)
h = 1616
Tmin = 0.977, Tmax = 0.983k = 1217
14182 measured reflectionsl = 1618
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)] = 0.064Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.221H atoms treated by a mixture of independent and constrained refinement
S = 1.01 w = 1/[σ2(Fo2) + (0.1569P)2 + 0.180P]
where P = (Fo2 + 2Fc2)/3
9024 reflections(Δ/σ)max = 0.001
699 parametersΔρmax = 0.55 e Å3
0 restraintsΔρmin = 0.28 e Å3
Crystal data top
C26H22N4O5·0.5C4H8O2γ = 116.524 (8)°
Mr = 514.53V = 2601 (2) Å3
Triclinic, P1Z = 4
a = 13.662 (5) ÅMo Kα radiation
b = 14.928 (6) ŵ = 0.09 mm1
c = 15.356 (10) ÅT = 293 K
α = 95.459 (11)°0.25 × 0.20 × 0.18 mm
β = 106.226 (11)°
Data collection top
Bruker APEXII CCD
diffractometer
9024 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2009)
6365 reflections with I > 2σ(I)
Tmin = 0.977, Tmax = 0.983Rint = 0.030
14182 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0640 restraints
wR(F2) = 0.221H atoms treated by a mixture of independent and constrained refinement
S = 1.01Δρmax = 0.55 e Å3
9024 reflectionsΔρmin = 0.28 e Å3
699 parameters
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
N40.00150 (17)0.67033 (16)0.44581 (13)0.0415 (5)
C320.0207 (2)0.57119 (19)0.41187 (14)0.0369 (5)
C330.08424 (19)0.57566 (18)0.41020 (14)0.0364 (5)
N30.16847 (17)0.68218 (15)0.44370 (13)0.0385 (5)
O80.17051 (17)0.83549 (14)0.48946 (14)0.0570 (5)
C280.0874 (2)0.48615 (19)0.37778 (15)0.0395 (6)
C310.1238 (2)0.4749 (2)0.38319 (16)0.0435 (6)
H310.19240.47040.38740.052*
N70.49747 (19)1.00469 (17)0.19708 (15)0.0473 (6)
O70.18151 (18)0.41080 (18)0.31586 (14)0.0672 (6)
C420.2215 (2)0.7413 (2)0.18920 (16)0.0443 (6)
H420.15960.73470.13910.053*
C370.2891 (2)0.7362 (2)0.44727 (16)0.0428 (6)
H37A0.33010.70200.47700.051*
H37B0.32800.80650.48590.051*
C430.2089 (2)0.7316 (2)0.27565 (17)0.0438 (6)
H430.13870.71910.28240.053*
C480.4438 (3)0.8462 (3)0.0169 (2)0.0594 (8)
H480.50870.89930.02370.071*
N80.6348 (2)0.9740 (3)0.1776 (2)0.0751 (8)
C380.29870 (19)0.74027 (18)0.35088 (15)0.0376 (5)
C510.6010 (2)1.0861 (3)0.2611 (2)0.0578 (8)
C300.1222 (2)0.3874 (2)0.34885 (16)0.0452 (6)
H300.19160.32410.32660.054*
C470.3581 (3)0.7671 (3)0.0945 (2)0.0671 (9)
H470.36530.76620.15300.081*
C410.3261 (2)0.76074 (19)0.17754 (16)0.0420 (6)
O90.61870 (19)1.16176 (18)0.31497 (16)0.0799 (8)
C340.1098 (2)0.73142 (19)0.46168 (16)0.0410 (6)
O60.29152 (18)0.54126 (19)0.44628 (16)0.0711 (6)
C490.4348 (2)0.8478 (2)0.07188 (18)0.0464 (6)
C520.1984 (2)0.4840 (2)0.38488 (18)0.0459 (6)
C500.5237 (2)0.9410 (2)0.15017 (18)0.0494 (7)
C440.3379 (2)0.7675 (2)0.08353 (17)0.0448 (6)
C400.4155 (2)0.7680 (2)0.25316 (18)0.0497 (7)
H400.48580.78040.24670.060*
O100.68645 (17)1.0687 (2)0.25039 (17)0.0800 (7)
C390.4018 (2)0.7572 (2)0.33852 (17)0.0478 (6)
H390.46260.76140.38810.057*
C290.0186 (2)0.3911 (2)0.34652 (16)0.0463 (6)
H290.01980.33040.32410.056*
C450.2510 (3)0.6889 (2)0.00359 (18)0.0566 (7)
H450.18530.63560.00930.068*
C270.2871 (3)0.4091 (3)0.3154 (3)0.0810 (11)
H27A0.34250.47530.31150.121*
H27B0.26740.35640.26240.121*
H27C0.32100.39450.37210.121*
C460.2609 (3)0.6887 (3)0.0840 (2)0.0695 (9)
H460.20180.63570.13600.083*
C360.1841 (5)1.0009 (3)0.5278 (4)0.1106 (17)
H36A0.25141.02330.58360.166*
H36B0.14171.03550.53710.166*
H36C0.20931.01740.47610.166*
C350.1068 (3)0.8872 (2)0.5069 (3)0.0742 (10)
H35A0.08280.86980.55960.089*
H35B0.03690.86460.45220.089*
C60.2024 (2)0.0933 (2)1.01931 (18)0.0485 (6)
H6A0.27680.07941.01650.058*
C40.0015 (3)0.1616 (2)1.10673 (19)0.0530 (7)
H40.06300.19381.16440.064*
N20.26434 (18)0.01972 (18)0.84744 (14)0.0486 (5)
C80.0689 (2)0.08916 (19)0.94074 (16)0.0406 (6)
C130.0667 (2)0.1405 (2)0.77654 (16)0.0435 (6)
N50.1701 (2)0.28881 (17)0.50981 (15)0.0489 (6)
C20.1521 (2)0.1676 (2)1.04685 (18)0.0517 (7)
N10.08666 (17)0.05155 (17)0.84652 (14)0.0442 (5)
O30.24105 (17)0.0311 (2)0.70583 (13)0.0698 (7)
C230.4272 (2)0.5237 (2)0.6411 (2)0.0602 (8)
H230.44930.52740.58890.072*
C70.1820 (2)0.06830 (19)0.93793 (17)0.0409 (6)
C190.3071 (2)0.4216 (2)0.72559 (18)0.0483 (6)
C200.3596 (3)0.5141 (3)0.7955 (2)0.0615 (8)
H200.33710.51240.84740.074*
O20.17589 (17)0.1522 (2)0.97154 (14)0.0765 (7)
O40.2578 (2)0.22670 (19)0.44503 (18)0.0806 (7)
C100.3664 (3)0.0870 (3)0.6532 (2)0.0675 (9)
H10A0.40860.11390.69450.081*
H10B0.38600.14480.60420.081*
C170.1361 (2)0.3196 (2)0.77355 (18)0.0493 (6)
H170.13000.37890.78490.059*
C180.0615 (2)0.2311 (2)0.79280 (17)0.0464 (6)
H180.00670.23220.81710.056*
C160.2204 (2)0.3224 (2)0.73761 (16)0.0458 (6)
C260.1515 (3)0.2183 (2)0.4336 (2)0.0660 (9)
O50.0632 (2)0.1582 (2)0.36806 (18)0.0934 (9)
C240.3419 (2)0.4284 (2)0.64672 (19)0.0492 (6)
C30.0267 (2)0.13857 (19)1.02678 (17)0.0431 (6)
C90.2031 (2)0.0113 (2)0.79755 (17)0.0475 (6)
C140.1498 (2)0.1413 (2)0.73955 (19)0.0513 (7)
H140.15480.08150.72780.062*
C110.3998 (3)0.0156 (3)0.6118 (3)0.0865 (11)
H11A0.38260.04010.66090.130*
H11B0.48220.05210.57520.130*
H11C0.35630.01190.57230.130*
C120.0084 (2)0.0423 (2)0.80109 (18)0.0468 (6)
H12A0.05590.01340.74410.056*
H12B0.04290.02330.84260.056*
C250.2861 (2)0.3394 (2)0.56306 (19)0.0495 (6)
C50.1081 (3)0.1391 (2)1.10392 (19)0.0549 (7)
H50.11950.15471.15910.066*
N60.3451 (2)0.3062 (2)0.5304 (2)0.0703 (7)
C150.2251 (2)0.2304 (2)0.7201 (2)0.0537 (7)
H150.27920.22910.69520.064*
O10.2246 (2)0.1998 (3)1.12383 (17)0.1087 (11)
C210.4437 (3)0.6082 (3)0.7900 (3)0.0750 (10)
H210.47630.66790.83750.090*
C10.2946 (3)0.1770 (3)0.9835 (3)0.0774 (10)
H1A0.33830.24720.98050.116*
H1B0.29350.13100.93460.116*
H1C0.33110.16931.04340.116*
C220.4786 (3)0.6127 (3)0.7140 (3)0.0754 (10)
H220.53640.67510.71110.091*
O120.7580 (4)0.5278 (3)0.8989 (2)0.1270 (12)
O110.9139 (5)0.5926 (4)1.0263 (3)0.177 (2)
C550.8719 (6)0.5628 (3)0.9449 (3)0.1081 (17)
C560.9303 (4)0.5469 (4)0.8823 (4)0.1221 (18)
H56A0.97920.61210.87230.183*
H56B0.87220.50020.82330.183*
H56C0.97770.51800.91060.183*
C530.5742 (6)0.4463 (7)0.9154 (5)0.155 (3)
H53A0.54380.43110.84810.233*
H53B0.52180.45710.93980.233*
H53C0.58140.38920.93400.233*
C540.6848 (8)0.5360 (6)0.9508 (5)0.173 (3)
H54A0.72250.54421.01700.207*
H54B0.67610.59630.94400.207*
H5A0.109 (3)0.300 (2)0.523 (2)0.056 (8)*
H70.428 (3)1.002 (3)0.187 (2)0.077 (11)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N40.0429 (11)0.0436 (12)0.0375 (10)0.0196 (10)0.0170 (9)0.0104 (9)
C320.0370 (12)0.0442 (14)0.0270 (10)0.0173 (11)0.0119 (9)0.0113 (9)
C330.0349 (12)0.0399 (13)0.0249 (10)0.0112 (10)0.0105 (9)0.0079 (9)
N30.0388 (10)0.0372 (11)0.0351 (10)0.0133 (9)0.0161 (8)0.0105 (8)
O80.0601 (11)0.0383 (10)0.0667 (12)0.0179 (9)0.0269 (10)0.0105 (9)
C280.0426 (13)0.0478 (14)0.0285 (11)0.0216 (11)0.0146 (10)0.0106 (10)
C310.0325 (12)0.0511 (16)0.0357 (11)0.0123 (11)0.0112 (9)0.0112 (11)
N70.0376 (12)0.0498 (13)0.0492 (12)0.0155 (10)0.0188 (10)0.0125 (10)
O70.0651 (12)0.0872 (16)0.0610 (12)0.0477 (12)0.0256 (10)0.0071 (11)
C420.0390 (13)0.0466 (14)0.0389 (12)0.0161 (11)0.0103 (10)0.0139 (11)
C370.0346 (12)0.0436 (14)0.0382 (12)0.0106 (11)0.0120 (10)0.0096 (10)
C430.0335 (12)0.0492 (15)0.0442 (13)0.0156 (11)0.0147 (10)0.0158 (11)
C480.0737 (19)0.083 (2)0.0556 (16)0.0522 (18)0.0419 (15)0.0360 (16)
N80.0481 (14)0.094 (2)0.0837 (18)0.0316 (15)0.0321 (13)0.0201 (16)
C380.0341 (12)0.0331 (12)0.0367 (11)0.0103 (10)0.0116 (9)0.0081 (9)
C510.0402 (14)0.0634 (19)0.0542 (16)0.0102 (14)0.0198 (12)0.0218 (15)
C300.0388 (13)0.0422 (14)0.0365 (12)0.0087 (11)0.0094 (10)0.0056 (10)
C470.104 (2)0.085 (2)0.0452 (16)0.064 (2)0.0411 (17)0.0250 (16)
C410.0470 (14)0.0376 (13)0.0414 (12)0.0184 (11)0.0192 (11)0.0136 (10)
O90.0623 (14)0.0657 (15)0.0689 (14)0.0020 (11)0.0222 (11)0.0045 (12)
C340.0468 (14)0.0383 (13)0.0331 (11)0.0172 (11)0.0145 (10)0.0093 (10)
O60.0507 (12)0.0819 (16)0.0742 (14)0.0383 (12)0.0080 (11)0.0090 (12)
C490.0532 (15)0.0574 (16)0.0476 (14)0.0356 (13)0.0277 (12)0.0212 (12)
C520.0474 (15)0.0520 (15)0.0438 (13)0.0271 (13)0.0179 (12)0.0180 (12)
C500.0459 (14)0.0658 (18)0.0513 (14)0.0302 (13)0.0284 (12)0.0306 (13)
C440.0561 (15)0.0480 (15)0.0413 (13)0.0305 (13)0.0230 (11)0.0172 (11)
C400.0442 (14)0.0674 (18)0.0489 (14)0.0315 (13)0.0232 (12)0.0240 (13)
O100.0391 (11)0.0911 (17)0.0845 (16)0.0140 (11)0.0207 (11)0.0165 (13)
C390.0394 (13)0.0599 (17)0.0413 (13)0.0225 (12)0.0133 (10)0.0167 (12)
C290.0507 (14)0.0424 (14)0.0356 (12)0.0166 (12)0.0142 (11)0.0041 (10)
C450.0722 (19)0.0518 (17)0.0434 (14)0.0287 (15)0.0201 (13)0.0149 (12)
C270.077 (2)0.112 (3)0.083 (2)0.064 (2)0.0418 (19)0.019 (2)
C460.102 (3)0.065 (2)0.0442 (15)0.0459 (19)0.0233 (15)0.0082 (14)
C360.149 (4)0.055 (2)0.148 (4)0.045 (2)0.091 (4)0.024 (2)
C350.090 (2)0.0496 (18)0.095 (2)0.0353 (17)0.050 (2)0.0159 (17)
C60.0527 (15)0.0542 (16)0.0526 (15)0.0314 (13)0.0281 (12)0.0185 (12)
C40.0603 (17)0.0525 (16)0.0419 (13)0.0269 (14)0.0165 (12)0.0059 (12)
N20.0444 (12)0.0584 (14)0.0462 (12)0.0263 (11)0.0188 (9)0.0145 (10)
C80.0462 (13)0.0383 (13)0.0439 (13)0.0229 (11)0.0213 (11)0.0130 (10)
C130.0476 (14)0.0560 (16)0.0361 (12)0.0314 (12)0.0168 (10)0.0151 (11)
N50.0532 (13)0.0457 (13)0.0501 (12)0.0236 (11)0.0251 (11)0.0060 (10)
C20.0480 (15)0.0460 (15)0.0494 (15)0.0205 (13)0.0099 (12)0.0015 (12)
N10.0410 (11)0.0545 (13)0.0408 (11)0.0247 (10)0.0177 (9)0.0129 (9)
O30.0498 (11)0.1100 (18)0.0404 (10)0.0368 (12)0.0126 (8)0.0065 (10)
C230.0451 (15)0.0601 (18)0.0777 (19)0.0260 (14)0.0231 (14)0.0257 (16)
C70.0454 (13)0.0412 (13)0.0443 (13)0.0249 (11)0.0191 (11)0.0187 (11)
C190.0442 (14)0.0562 (16)0.0476 (14)0.0297 (13)0.0115 (11)0.0160 (12)
C200.0601 (17)0.066 (2)0.0509 (16)0.0313 (16)0.0114 (13)0.0073 (14)
O20.0433 (11)0.124 (2)0.0536 (11)0.0380 (12)0.0153 (9)0.0127 (12)
O40.0998 (18)0.0762 (16)0.0925 (17)0.0526 (14)0.0595 (15)0.0127 (13)
C100.0561 (17)0.077 (2)0.0543 (16)0.0256 (17)0.0137 (14)0.0107 (15)
C170.0638 (17)0.0565 (16)0.0459 (14)0.0404 (14)0.0254 (12)0.0171 (12)
C180.0535 (15)0.0652 (17)0.0416 (13)0.0415 (14)0.0238 (11)0.0201 (12)
C160.0490 (14)0.0590 (16)0.0368 (12)0.0329 (13)0.0142 (11)0.0152 (11)
C260.085 (2)0.0547 (18)0.0666 (19)0.0336 (17)0.0434 (18)0.0087 (16)
O50.1028 (19)0.0788 (17)0.0718 (15)0.0287 (15)0.0355 (14)0.0206 (13)
C240.0394 (13)0.0524 (16)0.0566 (15)0.0226 (12)0.0185 (11)0.0143 (13)
C30.0470 (14)0.0386 (13)0.0451 (13)0.0229 (11)0.0157 (11)0.0105 (11)
C90.0438 (14)0.0573 (16)0.0435 (13)0.0254 (13)0.0177 (11)0.0130 (12)
C140.0632 (17)0.0549 (16)0.0604 (16)0.0407 (14)0.0342 (14)0.0215 (13)
C110.065 (2)0.082 (3)0.092 (3)0.0233 (19)0.0231 (19)0.026 (2)
C120.0454 (14)0.0538 (16)0.0454 (13)0.0269 (12)0.0200 (11)0.0071 (12)
C250.0497 (15)0.0544 (16)0.0561 (15)0.0286 (13)0.0284 (13)0.0212 (13)
C50.0701 (18)0.0612 (18)0.0462 (14)0.0372 (15)0.0302 (13)0.0154 (13)
N60.0742 (17)0.0773 (18)0.0840 (18)0.0489 (15)0.0430 (15)0.0210 (15)
C150.0577 (16)0.0594 (17)0.0657 (17)0.0365 (14)0.0371 (14)0.0228 (14)
O10.0606 (15)0.167 (3)0.0615 (15)0.0483 (17)0.0000 (12)0.0188 (16)
C210.0578 (19)0.056 (2)0.083 (2)0.0224 (16)0.0038 (17)0.0044 (17)
C10.0463 (17)0.103 (3)0.080 (2)0.0350 (18)0.0241 (15)0.018 (2)
C220.0520 (18)0.055 (2)0.102 (3)0.0182 (15)0.0180 (18)0.0210 (19)
O120.140 (3)0.168 (4)0.0779 (19)0.083 (3)0.036 (2)0.029 (2)
O110.254 (5)0.171 (4)0.086 (2)0.140 (4)0.012 (3)0.009 (2)
C550.154 (5)0.068 (3)0.065 (2)0.047 (3)0.002 (3)0.015 (2)
C560.106 (4)0.123 (4)0.113 (4)0.043 (3)0.021 (3)0.053 (3)
C530.157 (6)0.219 (8)0.154 (5)0.149 (6)0.054 (5)0.034 (5)
C540.221 (8)0.181 (7)0.127 (5)0.102 (7)0.081 (6)0.015 (5)
Geometric parameters (Å, º) top
N4—C341.310 (3)N2—C71.389 (3)
N4—C321.400 (3)C8—C31.408 (4)
C32—C311.404 (3)C8—N11.412 (3)
C32—C331.412 (3)C8—C71.420 (3)
C33—C281.404 (4)C13—C181.388 (4)
C33—N31.413 (3)C13—C141.400 (3)
N3—C341.368 (3)C13—C121.524 (4)
N3—C371.458 (3)N5—C251.357 (4)
O8—C341.345 (3)N5—C261.380 (4)
O8—C351.456 (4)N5—H5A1.00 (3)
C28—C291.409 (3)C2—O11.193 (3)
C28—C521.505 (4)C2—O21.313 (3)
C31—C301.373 (4)C2—C31.495 (4)
C31—H310.9300N1—C91.359 (3)
N7—C501.367 (4)N1—C121.476 (3)
N7—C511.380 (4)O3—C91.335 (3)
N7—H70.90 (4)O3—C101.450 (4)
O7—C521.337 (3)C23—C221.399 (5)
O7—C271.456 (4)C23—C241.411 (4)
C42—C411.393 (4)C23—H230.9300
C42—C431.398 (3)C19—C201.407 (4)
C42—H420.9300C19—C241.416 (4)
C37—C381.526 (3)C19—C161.496 (4)
C37—H37A0.9700C20—C211.392 (5)
C37—H37B0.9700C20—H200.9300
C43—C381.376 (4)O2—C11.445 (4)
C43—H430.9300O4—C261.359 (4)
C48—C471.379 (5)O4—N61.454 (4)
C48—C491.402 (4)C10—C111.465 (6)
C48—H480.9300C10—H10A0.9700
N8—C501.288 (4)C10—H10B0.9700
N8—O101.454 (4)C17—C181.383 (4)
C38—C391.388 (3)C17—C161.396 (4)
C51—O91.219 (4)C17—H170.9300
C51—O101.352 (4)C18—H180.9300
C30—C291.403 (4)C16—C151.407 (4)
C30—H300.9300C26—O51.206 (4)
C47—C461.388 (5)C24—C251.490 (4)
C47—H470.9300C14—C151.394 (4)
C41—C401.384 (4)C14—H140.9300
C41—C441.504 (3)C11—H11A0.9600
O6—C521.201 (3)C11—H11B0.9600
C49—C441.407 (4)C11—H11C0.9600
C49—C501.487 (4)C12—H12A0.9700
C44—C451.400 (4)C12—H12B0.9700
C40—C391.389 (4)C25—N61.298 (4)
C40—H400.9300C5—H50.9300
C39—H390.9300C15—H150.9300
C29—H290.9300C21—C221.373 (5)
C45—C461.388 (4)C21—H210.9300
C45—H450.9300C1—H1A0.9600
C27—H27A0.9600C1—H1B0.9600
C27—H27B0.9600C1—H1C0.9600
C27—H27C0.9600C22—H220.9300
C46—H460.9300O12—C551.336 (6)
C36—C351.485 (5)O12—C541.478 (8)
C36—H36A0.9600O11—C551.164 (5)
C36—H36B0.9600C55—C561.474 (8)
C36—H36C0.9600C56—H56A0.9600
C35—H35A0.9700C56—H56B0.9600
C35—H35B0.9700C56—H56C0.9600
C6—C51.387 (4)C53—C541.403 (9)
C6—C71.406 (4)C53—H53A0.9600
C6—H6A0.9300C53—H53B0.9600
C4—C51.367 (4)C53—H53C0.9600
C4—C31.416 (4)C54—H54A0.9700
C4—H40.9300C54—H54B0.9700
N2—C91.318 (3)
C34—N4—C32104.0 (2)C18—C13—C12123.8 (2)
N4—C32—C31129.7 (2)C14—C13—C12118.3 (2)
N4—C32—C33110.76 (19)C25—N5—C26108.1 (3)
C31—C32—C33119.5 (2)C25—N5—H5A126.5 (16)
C28—C33—C32121.6 (2)C26—N5—H5A125.4 (17)
C28—C33—N3134.1 (2)O1—C2—O2122.1 (3)
C32—C33—N3104.3 (2)O1—C2—C3124.0 (3)
C34—N3—C33105.87 (19)O2—C2—C3113.9 (2)
C34—N3—C37123.7 (2)C9—N1—C8106.07 (19)
C33—N3—C37129.9 (2)C9—N1—C12121.2 (2)
C34—O8—C35116.7 (2)C8—N1—C12132.5 (2)
C33—C28—C29117.4 (2)C9—O3—C10118.6 (2)
C33—C28—C52124.0 (2)C22—C23—C24120.0 (3)
C29—C28—C52118.2 (2)C22—C23—H23120.0
C30—C31—C32119.2 (2)C24—C23—H23120.0
C30—C31—H31120.4N2—C7—C6127.0 (2)
C32—C31—H31120.4N2—C7—C8111.1 (2)
C50—N7—C51108.3 (2)C6—C7—C8121.9 (2)
C50—N7—H7129 (2)C20—C19—C24116.7 (3)
C51—N7—H7122 (2)C20—C19—C16119.8 (2)
C52—O7—C27115.1 (2)C24—C19—C16123.4 (2)
C41—C42—C43120.5 (2)C21—C20—C19122.6 (3)
C41—C42—H42119.7C21—C20—H20118.7
C43—C42—H42119.7C19—C20—H20118.7
N3—C37—C38113.43 (18)C2—O2—C1118.2 (2)
N3—C37—H37A108.9C26—O4—N6109.2 (2)
C38—C37—H37A108.9O3—C10—C11108.5 (3)
N3—C37—H37B108.9O3—C10—H10A110.0
C38—C37—H37B108.9C11—C10—H10A110.0
H37A—C37—H37B107.7O3—C10—H10B110.0
C38—C43—C42121.1 (2)C11—C10—H10B110.0
C38—C43—H43119.5H10A—C10—H10B108.4
C42—C43—H43119.5C18—C17—C16121.8 (3)
C47—C48—C49121.1 (3)C18—C17—H17119.1
C47—C48—H48119.4C16—C17—H17119.1
C49—C48—H48119.4C17—C18—C13121.2 (2)
C50—N8—O10104.1 (3)C17—C18—H18119.4
C43—C38—C39118.3 (2)C13—C18—H18119.4
C43—C38—C37121.8 (2)C17—C16—C15117.1 (2)
C39—C38—C37119.8 (2)C17—C16—C19120.7 (3)
O9—C51—O10124.3 (3)C15—C16—C19122.0 (2)
O9—C51—N7130.4 (3)O5—C26—O4123.2 (3)
O10—C51—N7105.3 (3)O5—C26—N5131.0 (3)
C31—C30—C29121.6 (2)O4—C26—N5105.8 (3)
C31—C30—H30119.2C23—C24—C19120.7 (3)
C29—C30—H30119.2C23—C24—C25116.2 (2)
C48—C47—C46119.0 (3)C19—C24—C25122.9 (2)
C48—C47—H47120.5C8—C3—C4116.5 (2)
C46—C47—H47120.5C8—C3—C2129.0 (2)
C40—C41—C42118.1 (2)C4—C3—C2114.5 (2)
C40—C41—C44121.5 (2)N2—C9—O3128.1 (2)
C42—C41—C44120.3 (2)N2—C9—N1115.2 (2)
N4—C34—O8127.7 (3)O3—C9—N1116.7 (2)
N4—C34—N3115.0 (2)C15—C14—C13120.9 (3)
O8—C34—N3117.2 (2)C15—C14—H14119.5
C48—C49—C44120.2 (3)C13—C14—H14119.5
C48—C49—C50118.1 (2)C10—C11—H11A109.5
C44—C49—C50121.4 (2)C10—C11—H11B109.5
O6—C52—O7123.9 (3)H11A—C11—H11B109.5
O6—C52—C28123.6 (2)C10—C11—H11C109.5
O7—C52—C28112.5 (2)H11A—C11—H11C109.5
N8—C50—N7112.5 (3)H11B—C11—H11C109.5
N8—C50—C49123.6 (3)N1—C12—C13114.3 (2)
N7—C50—C49123.8 (2)N1—C12—H12A108.7
C45—C44—C49117.7 (2)C13—C12—H12A108.7
C45—C44—C41119.2 (2)N1—C12—H12B108.7
C49—C44—C41123.1 (2)C13—C12—H12B108.7
C41—C40—C39121.0 (2)H12A—C12—H12B107.6
C41—C40—H40119.5N6—C25—N5112.9 (3)
C39—C40—H40119.5N6—C25—C24123.1 (3)
C51—O10—N8109.8 (2)N5—C25—C24123.9 (2)
C38—C39—C40120.9 (2)C4—C5—C6120.4 (2)
C38—C39—H39119.5C4—C5—H5119.8
C40—C39—H39119.5C6—C5—H5119.8
C30—C29—C28120.6 (2)C25—N6—O4104.0 (2)
C30—C29—H29119.7C14—C15—C16121.0 (2)
C28—C29—H29119.7C14—C15—H15119.5
C46—C45—C44121.4 (3)C16—C15—H15119.5
C46—C45—H45119.3C22—C21—C20119.8 (3)
C44—C45—H45119.3C22—C21—H21120.1
O7—C27—H27A109.5C20—C21—H21120.1
O7—C27—H27B109.5O2—C1—H1A109.5
H27A—C27—H27B109.5O2—C1—H1B109.5
O7—C27—H27C109.5H1A—C1—H1B109.5
H27A—C27—H27C109.5O2—C1—H1C109.5
H27B—C27—H27C109.5H1A—C1—H1C109.5
C45—C46—C47120.5 (3)H1B—C1—H1C109.5
C45—C46—H46119.7C21—C22—C23120.2 (3)
C47—C46—H46119.7C21—C22—H22119.9
C35—C36—H36A109.5C23—C22—H22119.9
C35—C36—H36B109.5C55—O12—C54119.6 (5)
H36A—C36—H36B109.5O11—C55—O12121.7 (6)
C35—C36—H36C109.5O11—C55—C56125.8 (6)
H36A—C36—H36C109.5O12—C55—C56112.1 (4)
H36B—C36—H36C109.5C55—C56—H56A109.5
O8—C35—C36109.0 (3)C55—C56—H56B109.5
O8—C35—H35A109.9H56A—C56—H56B109.5
C36—C35—H35A109.9C55—C56—H56C109.5
O8—C35—H35B109.9H56A—C56—H56C109.5
C36—C35—H35B109.9H56B—C56—H56C109.5
H35A—C35—H35B108.3C54—C53—H53A109.5
C5—C6—C7118.0 (2)C54—C53—H53B109.5
C5—C6—H6A121.0H53A—C53—H53B109.5
C7—C6—H6A121.0C54—C53—H53C109.5
C5—C4—C3123.7 (3)H53A—C53—H53C109.5
C5—C4—H4118.1H53B—C53—H53C109.5
C3—C4—H4118.1C53—C54—O12109.4 (6)
C9—N2—C7103.8 (2)C53—C54—H54A109.8
C3—C8—N1136.7 (2)O12—C54—H54A109.8
C3—C8—C7119.5 (2)C53—C54—H54B109.8
N1—C8—C7103.9 (2)O12—C54—H54B109.8
C18—C13—C14117.9 (2)H54A—C54—H54B108.2
C34—N4—C32—C31180.0 (2)C3—C8—N1—C125.7 (5)
C34—N4—C32—C331.3 (2)C7—C8—N1—C12175.2 (3)
N4—C32—C33—C28179.2 (2)C9—N2—C7—C6178.2 (3)
C31—C32—C33—C282.0 (3)C9—N2—C7—C80.2 (3)
N4—C32—C33—N30.6 (2)C5—C6—C7—N2178.0 (3)
C31—C32—C33—N3179.5 (2)C5—C6—C7—C80.2 (4)
C28—C33—N3—C34178.0 (2)C3—C8—C7—N2179.9 (2)
C32—C33—N3—C340.3 (2)N1—C8—C7—N20.6 (3)
C28—C33—N3—C376.6 (4)C3—C8—C7—C61.6 (4)
C32—C33—N3—C37171.7 (2)N1—C8—C7—C6179.1 (2)
C32—C33—C28—C290.2 (3)C24—C19—C20—C211.5 (5)
N3—C33—C28—C29177.9 (2)C16—C19—C20—C21177.8 (3)
C32—C33—C28—C52172.4 (2)O1—C2—O2—C11.0 (5)
N3—C33—C28—C529.5 (4)C3—C2—O2—C1179.5 (3)
N4—C32—C31—C30177.6 (2)C9—O3—C10—C1193.9 (3)
C33—C32—C31—C303.8 (3)C16—C17—C18—C130.4 (4)
C34—N3—C37—C3899.7 (3)C14—C13—C18—C170.3 (4)
C33—N3—C37—C3870.3 (3)C12—C13—C18—C17176.6 (2)
C41—C42—C43—C380.5 (4)C18—C17—C16—C151.1 (4)
C42—C43—C38—C391.0 (4)C18—C17—C16—C19174.4 (2)
C42—C43—C38—C37176.4 (2)C20—C19—C16—C1741.4 (4)
N3—C37—C38—C4323.8 (3)C24—C19—C16—C17139.3 (3)
N3—C37—C38—C39158.9 (2)C20—C19—C16—C15133.8 (3)
C50—N7—C51—O9177.4 (3)C24—C19—C16—C1545.4 (4)
C50—N7—C51—O100.1 (3)N6—O4—C26—O5179.7 (3)
C32—C31—C30—C293.6 (4)N6—O4—C26—N50.9 (3)
C49—C48—C47—C460.8 (5)C25—N5—C26—O5178.9 (4)
C43—C42—C41—C401.3 (4)C25—N5—C26—O41.8 (3)
C43—C42—C41—C44177.9 (2)C22—C23—C24—C190.2 (4)
C32—N4—C34—O8175.5 (2)C22—C23—C24—C25175.9 (3)
C32—N4—C34—N31.6 (3)C20—C19—C24—C231.5 (4)
C35—O8—C34—N42.0 (4)C16—C19—C24—C23177.8 (3)
C35—O8—C34—N3179.0 (2)C20—C19—C24—C25174.0 (3)
C33—N3—C34—N41.2 (3)C16—C19—C24—C256.7 (4)
C37—N3—C34—N4173.32 (19)N1—C8—C3—C4179.2 (3)
C33—N3—C34—O8176.2 (2)C7—C8—C3—C41.9 (4)
C37—N3—C34—O84.1 (3)N1—C8—C3—C21.5 (5)
C47—C48—C49—C440.7 (5)C7—C8—C3—C2179.6 (3)
C47—C48—C49—C50173.5 (3)C5—C4—C3—C80.4 (4)
C27—O7—C52—O64.3 (4)C5—C4—C3—C2178.5 (3)
C27—O7—C52—C28176.3 (2)O1—C2—C3—C8172.0 (3)
C33—C28—C52—O630.0 (4)O2—C2—C3—C86.5 (4)
C29—C28—C52—O6142.6 (3)O1—C2—C3—C45.8 (5)
C33—C28—C52—O7150.6 (2)O2—C2—C3—C4175.8 (3)
C29—C28—C52—O736.8 (3)C7—N2—C9—O3179.3 (3)
O10—N8—C50—N70.4 (3)C7—N2—C9—N11.1 (3)
O10—N8—C50—C49176.6 (2)C10—O3—C9—N28.4 (5)
C51—N7—C50—N80.3 (3)C10—O3—C9—N1172.0 (3)
C51—N7—C50—C49176.5 (2)C8—N1—C9—N21.5 (3)
C48—C49—C50—N858.7 (4)C12—N1—C9—N2176.4 (2)
C44—C49—C50—N8127.2 (3)C8—N1—C9—O3178.8 (2)
C48—C49—C50—N7117.1 (3)C12—N1—C9—O33.9 (4)
C44—C49—C50—N757.0 (4)C18—C13—C14—C150.3 (4)
C48—C49—C44—C451.7 (4)C12—C13—C14—C15176.8 (2)
C50—C49—C44—C45172.3 (3)C9—N1—C12—C13102.2 (3)
C48—C49—C44—C41176.1 (3)C8—N1—C12—C1384.5 (3)
C50—C49—C44—C419.9 (4)C18—C13—C12—N11.5 (4)
C40—C41—C44—C45126.8 (3)C14—C13—C12—N1175.4 (2)
C42—C41—C44—C4549.7 (4)C26—N5—C25—N62.1 (3)
C40—C41—C44—C4950.9 (4)C26—N5—C25—C24174.1 (3)
C42—C41—C44—C49132.6 (3)C23—C24—C25—N658.8 (4)
C42—C41—C40—C390.6 (4)C19—C24—C25—N6125.5 (3)
C44—C41—C40—C39177.2 (3)C23—C24—C25—N5117.0 (3)
O9—C51—O10—N8177.4 (3)C19—C24—C25—N558.7 (4)
N7—C51—O10—N80.1 (3)C3—C4—C5—C61.5 (5)
C50—N8—O10—C510.3 (3)C7—C6—C5—C41.8 (4)
C43—C38—C39—C401.7 (4)N5—C25—N6—O41.4 (3)
C37—C38—C39—C40175.7 (3)C24—C25—N6—O4174.8 (3)
C41—C40—C39—C380.9 (4)C26—O4—N6—C250.3 (3)
C31—C30—C29—C281.4 (4)C13—C14—C15—C160.4 (4)
C33—C28—C29—C300.5 (3)C17—C16—C15—C141.1 (4)
C52—C28—C29—C30172.6 (2)C19—C16—C15—C14174.4 (3)
C49—C44—C45—C461.3 (5)C19—C20—C21—C220.2 (5)
C41—C44—C45—C46176.6 (3)C20—C21—C22—C231.9 (5)
C44—C45—C46—C470.2 (5)C24—C23—C22—C211.9 (5)
C48—C47—C46—C451.2 (5)C54—O12—C55—O115.9 (8)
C34—O8—C35—C36174.6 (3)C54—O12—C55—C56179.2 (6)
C3—C8—N1—C9179.8 (3)C55—O12—C54—C53140.9 (6)
C7—C8—N1—C91.2 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N5—H5A···N4i1.011.852.862 (3)176
N7—H7···N2i0.902.012.905 (3)173
C12—H12A···O5ii0.972.583.421 (4)145
C30—H30···O9iii0.932.583.484 (3)163
Symmetry codes: (i) x, y+1, z+1; (ii) x, y, z+1; (iii) x1, y1, z.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N5—H5A···N4i1.011.852.862 (3)176
N7—H7···N2i0.902.012.905 (3)173
C12—H12A···O5ii0.972.583.421 (4)145
C30—H30···O9iii0.932.583.484 (3)163
Symmetry codes: (i) x, y+1, z+1; (ii) x, y, z+1; (iii) x1, y1, z.
 

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