The title compound, C
26H
22N
4O
5 (systematic name: methyl 2-ethoxy-1-{4-[2-(5-oxo-4,5-dihydro-1,2,4-oxadiazol-3-yl)phenyl]benzyl}-1
H-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}-1
H-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—C
m (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
CCDC reference: 934880
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean
(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
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.
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.
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).
Methyl
2-ethoxy-1-{4-[2-(5-oxo-4,5-dihydro-1,2,4-oxadiazol-3-yl)phenyl]benzyl}-1
H-1,3-benzodiazole-7-carboxylate ethyl acetate hemisolvate
top
Crystal data top
C26H22N4O5·0.5C4H8O2 | Z = 4 |
Mr = 514.53 | F(000) = 1080 |
Triclinic, P1 | Dx = 1.314 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 13.662 (5) Å | Cell parameters from 5677 reflections |
b = 14.928 (6) Å | θ = 2.4–28.3° |
c = 15.356 (10) Å | µ = 0.09 mm−1 |
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 tube | 6365 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.030 |
phi and ω scans | θmax = 25.0°, θmin = 1.4° |
Absorption correction: multi-scan (SADABS; Bruker, 2009) | h = −16→16 |
Tmin = 0.977, Tmax = 0.983 | k = −12→17 |
14182 measured reflections | l = −16→18 |
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)] = 0.064 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.221 | H 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 parameters | Δρmax = 0.55 e Å−3 |
0 restraints | Δρmin = −0.28 e Å−3 |
Crystal data top
C26H22N4O5·0.5C4H8O2 | γ = 116.524 (8)° |
Mr = 514.53 | V = 2601 (2) Å3 |
Triclinic, P1 | Z = 4 |
a = 13.662 (5) Å | Mo Kα radiation |
b = 14.928 (6) Å | µ = 0.09 mm−1 |
c = 15.356 (10) Å | T = 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 = 0.983 | Rint = 0.030 |
14182 measured reflections | |
Refinement top
R[F2 > 2σ(F2)] = 0.064 | 0 restraints |
wR(F2) = 0.221 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.01 | Δρmax = 0.55 e Å−3 |
9024 reflections | Δρmin = −0.28 e Å−3 |
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 | x | y | z | Uiso*/Ueq | |
N4 | −0.00150 (17) | 0.67033 (16) | 0.44581 (13) | 0.0415 (5) | |
C32 | −0.0207 (2) | 0.57119 (19) | 0.41187 (14) | 0.0369 (5) | |
C33 | 0.08424 (19) | 0.57566 (18) | 0.41020 (14) | 0.0364 (5) | |
N3 | 0.16847 (17) | 0.68218 (15) | 0.44370 (13) | 0.0385 (5) | |
O8 | 0.17051 (17) | 0.83549 (14) | 0.48946 (14) | 0.0570 (5) | |
C28 | 0.0874 (2) | 0.48615 (19) | 0.37778 (15) | 0.0395 (6) | |
C31 | −0.1238 (2) | 0.4749 (2) | 0.38319 (16) | 0.0435 (6) | |
H31 | −0.1924 | 0.4704 | 0.3874 | 0.052* | |
N7 | 0.49747 (19) | 1.00469 (17) | 0.19708 (15) | 0.0473 (6) | |
O7 | 0.18151 (18) | 0.41080 (18) | 0.31586 (14) | 0.0672 (6) | |
C42 | 0.2215 (2) | 0.7413 (2) | 0.18920 (16) | 0.0443 (6) | |
H42 | 0.1596 | 0.7347 | 0.1391 | 0.053* | |
C37 | 0.2891 (2) | 0.7362 (2) | 0.44727 (16) | 0.0428 (6) | |
H37A | 0.3301 | 0.7020 | 0.4770 | 0.051* | |
H37B | 0.3280 | 0.8065 | 0.4859 | 0.051* | |
C43 | 0.2089 (2) | 0.7316 (2) | 0.27565 (17) | 0.0438 (6) | |
H43 | 0.1387 | 0.7191 | 0.2824 | 0.053* | |
C48 | 0.4438 (3) | 0.8462 (3) | −0.0169 (2) | 0.0594 (8) | |
H48 | 0.5087 | 0.8993 | −0.0237 | 0.071* | |
N8 | 0.6348 (2) | 0.9740 (3) | 0.1776 (2) | 0.0751 (8) | |
C38 | 0.29870 (19) | 0.74027 (18) | 0.35088 (15) | 0.0376 (5) | |
C51 | 0.6010 (2) | 1.0861 (3) | 0.2611 (2) | 0.0578 (8) | |
C30 | −0.1222 (2) | 0.3874 (2) | 0.34885 (16) | 0.0452 (6) | |
H30 | −0.1916 | 0.3241 | 0.3266 | 0.054* | |
C47 | 0.3581 (3) | 0.7671 (3) | −0.0945 (2) | 0.0671 (9) | |
H47 | 0.3653 | 0.7662 | −0.1530 | 0.081* | |
C41 | 0.3261 (2) | 0.76074 (19) | 0.17754 (16) | 0.0420 (6) | |
O9 | 0.61870 (19) | 1.16176 (18) | 0.31497 (16) | 0.0799 (8) | |
C34 | 0.1098 (2) | 0.73142 (19) | 0.46168 (16) | 0.0410 (6) | |
O6 | 0.29152 (18) | 0.54126 (19) | 0.44628 (16) | 0.0711 (6) | |
C49 | 0.4348 (2) | 0.8478 (2) | 0.07188 (18) | 0.0464 (6) | |
C52 | 0.1984 (2) | 0.4840 (2) | 0.38488 (18) | 0.0459 (6) | |
C50 | 0.5237 (2) | 0.9410 (2) | 0.15017 (18) | 0.0494 (7) | |
C44 | 0.3379 (2) | 0.7675 (2) | 0.08353 (17) | 0.0448 (6) | |
C40 | 0.4155 (2) | 0.7680 (2) | 0.25316 (18) | 0.0497 (7) | |
H40 | 0.4858 | 0.7804 | 0.2467 | 0.060* | |
O10 | 0.68645 (17) | 1.0687 (2) | 0.25039 (17) | 0.0800 (7) | |
C39 | 0.4018 (2) | 0.7572 (2) | 0.33852 (17) | 0.0478 (6) | |
H39 | 0.4626 | 0.7614 | 0.3881 | 0.057* | |
C29 | −0.0186 (2) | 0.3911 (2) | 0.34652 (16) | 0.0463 (6) | |
H29 | −0.0198 | 0.3304 | 0.3241 | 0.056* | |
C45 | 0.2510 (3) | 0.6889 (2) | 0.00359 (18) | 0.0566 (7) | |
H45 | 0.1853 | 0.6356 | 0.0093 | 0.068* | |
C27 | 0.2871 (3) | 0.4091 (3) | 0.3154 (3) | 0.0810 (11) | |
H27A | 0.3425 | 0.4753 | 0.3115 | 0.121* | |
H27B | 0.2674 | 0.3564 | 0.2624 | 0.121* | |
H27C | 0.3210 | 0.3945 | 0.3721 | 0.121* | |
C46 | 0.2609 (3) | 0.6887 (3) | −0.0840 (2) | 0.0695 (9) | |
H46 | 0.2018 | 0.6357 | −0.1360 | 0.083* | |
C36 | 0.1841 (5) | 1.0009 (3) | 0.5278 (4) | 0.1106 (17) | |
H36A | 0.2514 | 1.0233 | 0.5836 | 0.166* | |
H36B | 0.1417 | 1.0355 | 0.5371 | 0.166* | |
H36C | 0.2093 | 1.0174 | 0.4761 | 0.166* | |
C35 | 0.1068 (3) | 0.8872 (2) | 0.5069 (3) | 0.0742 (10) | |
H35A | 0.0828 | 0.8698 | 0.5596 | 0.089* | |
H35B | 0.0369 | 0.8646 | 0.4522 | 0.089* | |
C6 | −0.2024 (2) | 0.0933 (2) | 1.01931 (18) | 0.0485 (6) | |
H6A | −0.2768 | 0.0794 | 1.0165 | 0.058* | |
C4 | 0.0015 (3) | 0.1616 (2) | 1.10673 (19) | 0.0530 (7) | |
H4 | 0.0630 | 0.1938 | 1.1644 | 0.064* | |
N2 | −0.26434 (18) | 0.01972 (18) | 0.84744 (14) | 0.0486 (5) | |
C8 | −0.0689 (2) | 0.08916 (19) | 0.94074 (16) | 0.0406 (6) | |
C13 | 0.0667 (2) | 0.1405 (2) | 0.77654 (16) | 0.0435 (6) | |
N5 | 0.1701 (2) | 0.28881 (17) | 0.50981 (15) | 0.0489 (6) | |
C2 | 0.1521 (2) | 0.1676 (2) | 1.04685 (18) | 0.0517 (7) | |
N1 | −0.08666 (17) | 0.05155 (17) | 0.84652 (14) | 0.0442 (5) | |
O3 | −0.24105 (17) | −0.0311 (2) | 0.70583 (13) | 0.0698 (7) | |
C23 | 0.4272 (2) | 0.5237 (2) | 0.6411 (2) | 0.0602 (8) | |
H23 | 0.4493 | 0.5274 | 0.5889 | 0.072* | |
C7 | −0.1820 (2) | 0.06830 (19) | 0.93793 (17) | 0.0409 (6) | |
C19 | 0.3071 (2) | 0.4216 (2) | 0.72559 (18) | 0.0483 (6) | |
C20 | 0.3596 (3) | 0.5141 (3) | 0.7955 (2) | 0.0615 (8) | |
H20 | 0.3371 | 0.5124 | 0.8474 | 0.074* | |
O2 | 0.17589 (17) | 0.1522 (2) | 0.97154 (14) | 0.0765 (7) | |
O4 | 0.2578 (2) | 0.22670 (19) | 0.44503 (18) | 0.0806 (7) | |
C10 | −0.3664 (3) | −0.0870 (3) | 0.6532 (2) | 0.0675 (9) | |
H10A | −0.4086 | −0.1139 | 0.6945 | 0.081* | |
H10B | −0.3860 | −0.1448 | 0.6042 | 0.081* | |
C17 | 0.1361 (2) | 0.3196 (2) | 0.77355 (18) | 0.0493 (6) | |
H17 | 0.1300 | 0.3789 | 0.7849 | 0.059* | |
C18 | 0.0615 (2) | 0.2311 (2) | 0.79280 (17) | 0.0464 (6) | |
H18 | 0.0067 | 0.2322 | 0.8171 | 0.056* | |
C16 | 0.2204 (2) | 0.3224 (2) | 0.73761 (16) | 0.0458 (6) | |
C26 | 0.1515 (3) | 0.2183 (2) | 0.4336 (2) | 0.0660 (9) | |
O5 | 0.0632 (2) | 0.1582 (2) | 0.36806 (18) | 0.0934 (9) | |
C24 | 0.3419 (2) | 0.4284 (2) | 0.64672 (19) | 0.0492 (6) | |
C3 | 0.0267 (2) | 0.13857 (19) | 1.02678 (17) | 0.0431 (6) | |
C9 | −0.2031 (2) | 0.0113 (2) | 0.79755 (17) | 0.0475 (6) | |
C14 | 0.1498 (2) | 0.1413 (2) | 0.73955 (19) | 0.0513 (7) | |
H14 | 0.1548 | 0.0815 | 0.7278 | 0.062* | |
C11 | −0.3998 (3) | −0.0156 (3) | 0.6118 (3) | 0.0865 (11) | |
H11A | −0.3826 | 0.0401 | 0.6609 | 0.130* | |
H11B | −0.4822 | −0.0521 | 0.5752 | 0.130* | |
H11C | −0.3563 | 0.0119 | 0.5723 | 0.130* | |
C12 | −0.0084 (2) | 0.0423 (2) | 0.80109 (18) | 0.0468 (6) | |
H12A | −0.0559 | −0.0134 | 0.7441 | 0.056* | |
H12B | 0.0429 | 0.0233 | 0.8426 | 0.056* | |
C25 | 0.2861 (2) | 0.3394 (2) | 0.56306 (19) | 0.0495 (6) | |
C5 | −0.1081 (3) | 0.1391 (2) | 1.10392 (19) | 0.0549 (7) | |
H5 | −0.1195 | 0.1547 | 1.1591 | 0.066* | |
N6 | 0.3451 (2) | 0.3062 (2) | 0.5304 (2) | 0.0703 (7) | |
C15 | 0.2251 (2) | 0.2304 (2) | 0.7201 (2) | 0.0537 (7) | |
H15 | 0.2792 | 0.2291 | 0.6952 | 0.064* | |
O1 | 0.2246 (2) | 0.1998 (3) | 1.12383 (17) | 0.1087 (11) | |
C21 | 0.4437 (3) | 0.6082 (3) | 0.7900 (3) | 0.0750 (10) | |
H21 | 0.4763 | 0.6679 | 0.8375 | 0.090* | |
C1 | 0.2946 (3) | 0.1770 (3) | 0.9835 (3) | 0.0774 (10) | |
H1A | 0.3383 | 0.2472 | 0.9805 | 0.116* | |
H1B | 0.2935 | 0.1310 | 0.9346 | 0.116* | |
H1C | 0.3311 | 0.1693 | 1.0434 | 0.116* | |
C22 | 0.4786 (3) | 0.6127 (3) | 0.7140 (3) | 0.0754 (10) | |
H22 | 0.5364 | 0.6751 | 0.7111 | 0.091* | |
O12 | 0.7580 (4) | 0.5278 (3) | 0.8989 (2) | 0.1270 (12) | |
O11 | 0.9139 (5) | 0.5926 (4) | 1.0263 (3) | 0.177 (2) | |
C55 | 0.8719 (6) | 0.5628 (3) | 0.9449 (3) | 0.1081 (17) | |
C56 | 0.9303 (4) | 0.5469 (4) | 0.8823 (4) | 0.1221 (18) | |
H56A | 0.9792 | 0.6121 | 0.8723 | 0.183* | |
H56B | 0.8722 | 0.5002 | 0.8233 | 0.183* | |
H56C | 0.9777 | 0.5180 | 0.9106 | 0.183* | |
C53 | 0.5742 (6) | 0.4463 (7) | 0.9154 (5) | 0.155 (3) | |
H53A | 0.5438 | 0.4311 | 0.8481 | 0.233* | |
H53B | 0.5218 | 0.4571 | 0.9398 | 0.233* | |
H53C | 0.5814 | 0.3892 | 0.9340 | 0.233* | |
C54 | 0.6848 (8) | 0.5360 (6) | 0.9508 (5) | 0.173 (3) | |
H54A | 0.7225 | 0.5442 | 1.0170 | 0.207* | |
H54B | 0.6761 | 0.5963 | 0.9440 | 0.207* | |
H5A | 0.109 (3) | 0.300 (2) | 0.523 (2) | 0.056 (8)* | |
H7 | 0.428 (3) | 1.002 (3) | 0.187 (2) | 0.077 (11)* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
N4 | 0.0429 (11) | 0.0436 (12) | 0.0375 (10) | 0.0196 (10) | 0.0170 (9) | 0.0104 (9) |
C32 | 0.0370 (12) | 0.0442 (14) | 0.0270 (10) | 0.0173 (11) | 0.0119 (9) | 0.0113 (9) |
C33 | 0.0349 (12) | 0.0399 (13) | 0.0249 (10) | 0.0112 (10) | 0.0105 (9) | 0.0079 (9) |
N3 | 0.0388 (10) | 0.0372 (11) | 0.0351 (10) | 0.0133 (9) | 0.0161 (8) | 0.0105 (8) |
O8 | 0.0601 (11) | 0.0383 (10) | 0.0667 (12) | 0.0179 (9) | 0.0269 (10) | 0.0105 (9) |
C28 | 0.0426 (13) | 0.0478 (14) | 0.0285 (11) | 0.0216 (11) | 0.0146 (10) | 0.0106 (10) |
C31 | 0.0325 (12) | 0.0511 (16) | 0.0357 (11) | 0.0123 (11) | 0.0112 (9) | 0.0112 (11) |
N7 | 0.0376 (12) | 0.0498 (13) | 0.0492 (12) | 0.0155 (10) | 0.0188 (10) | 0.0125 (10) |
O7 | 0.0651 (12) | 0.0872 (16) | 0.0610 (12) | 0.0477 (12) | 0.0256 (10) | 0.0071 (11) |
C42 | 0.0390 (13) | 0.0466 (14) | 0.0389 (12) | 0.0161 (11) | 0.0103 (10) | 0.0139 (11) |
C37 | 0.0346 (12) | 0.0436 (14) | 0.0382 (12) | 0.0106 (11) | 0.0120 (10) | 0.0096 (10) |
C43 | 0.0335 (12) | 0.0492 (15) | 0.0442 (13) | 0.0156 (11) | 0.0147 (10) | 0.0158 (11) |
C48 | 0.0737 (19) | 0.083 (2) | 0.0556 (16) | 0.0522 (18) | 0.0419 (15) | 0.0360 (16) |
N8 | 0.0481 (14) | 0.094 (2) | 0.0837 (18) | 0.0316 (15) | 0.0321 (13) | 0.0201 (16) |
C38 | 0.0341 (12) | 0.0331 (12) | 0.0367 (11) | 0.0103 (10) | 0.0116 (9) | 0.0081 (9) |
C51 | 0.0402 (14) | 0.0634 (19) | 0.0542 (16) | 0.0102 (14) | 0.0198 (12) | 0.0218 (15) |
C30 | 0.0388 (13) | 0.0422 (14) | 0.0365 (12) | 0.0087 (11) | 0.0094 (10) | 0.0056 (10) |
C47 | 0.104 (2) | 0.085 (2) | 0.0452 (16) | 0.064 (2) | 0.0411 (17) | 0.0250 (16) |
C41 | 0.0470 (14) | 0.0376 (13) | 0.0414 (12) | 0.0184 (11) | 0.0192 (11) | 0.0136 (10) |
O9 | 0.0623 (14) | 0.0657 (15) | 0.0689 (14) | 0.0020 (11) | 0.0222 (11) | −0.0045 (12) |
C34 | 0.0468 (14) | 0.0383 (13) | 0.0331 (11) | 0.0172 (11) | 0.0145 (10) | 0.0093 (10) |
O6 | 0.0507 (12) | 0.0819 (16) | 0.0742 (14) | 0.0383 (12) | 0.0080 (11) | 0.0090 (12) |
C49 | 0.0532 (15) | 0.0574 (16) | 0.0476 (14) | 0.0356 (13) | 0.0277 (12) | 0.0212 (12) |
C52 | 0.0474 (15) | 0.0520 (15) | 0.0438 (13) | 0.0271 (13) | 0.0179 (12) | 0.0180 (12) |
C50 | 0.0459 (14) | 0.0658 (18) | 0.0513 (14) | 0.0302 (13) | 0.0284 (12) | 0.0306 (13) |
C44 | 0.0561 (15) | 0.0480 (15) | 0.0413 (13) | 0.0305 (13) | 0.0230 (11) | 0.0172 (11) |
C40 | 0.0442 (14) | 0.0674 (18) | 0.0489 (14) | 0.0315 (13) | 0.0232 (12) | 0.0240 (13) |
O10 | 0.0391 (11) | 0.0911 (17) | 0.0845 (16) | 0.0140 (11) | 0.0207 (11) | 0.0165 (13) |
C39 | 0.0394 (13) | 0.0599 (17) | 0.0413 (13) | 0.0225 (12) | 0.0133 (10) | 0.0167 (12) |
C29 | 0.0507 (14) | 0.0424 (14) | 0.0356 (12) | 0.0166 (12) | 0.0142 (11) | 0.0041 (10) |
C45 | 0.0722 (19) | 0.0518 (17) | 0.0434 (14) | 0.0287 (15) | 0.0201 (13) | 0.0149 (12) |
C27 | 0.077 (2) | 0.112 (3) | 0.083 (2) | 0.064 (2) | 0.0418 (19) | 0.019 (2) |
C46 | 0.102 (3) | 0.065 (2) | 0.0442 (15) | 0.0459 (19) | 0.0233 (15) | 0.0082 (14) |
C36 | 0.149 (4) | 0.055 (2) | 0.148 (4) | 0.045 (2) | 0.091 (4) | 0.024 (2) |
C35 | 0.090 (2) | 0.0496 (18) | 0.095 (2) | 0.0353 (17) | 0.050 (2) | 0.0159 (17) |
C6 | 0.0527 (15) | 0.0542 (16) | 0.0526 (15) | 0.0314 (13) | 0.0281 (12) | 0.0185 (12) |
C4 | 0.0603 (17) | 0.0525 (16) | 0.0419 (13) | 0.0269 (14) | 0.0165 (12) | 0.0059 (12) |
N2 | 0.0444 (12) | 0.0584 (14) | 0.0462 (12) | 0.0263 (11) | 0.0188 (9) | 0.0145 (10) |
C8 | 0.0462 (13) | 0.0383 (13) | 0.0439 (13) | 0.0229 (11) | 0.0213 (11) | 0.0130 (10) |
C13 | 0.0476 (14) | 0.0560 (16) | 0.0361 (12) | 0.0314 (12) | 0.0168 (10) | 0.0151 (11) |
N5 | 0.0532 (13) | 0.0457 (13) | 0.0501 (12) | 0.0236 (11) | 0.0251 (11) | 0.0060 (10) |
C2 | 0.0480 (15) | 0.0460 (15) | 0.0494 (15) | 0.0205 (13) | 0.0099 (12) | 0.0015 (12) |
N1 | 0.0410 (11) | 0.0545 (13) | 0.0408 (11) | 0.0247 (10) | 0.0177 (9) | 0.0129 (9) |
O3 | 0.0498 (11) | 0.1100 (18) | 0.0404 (10) | 0.0368 (12) | 0.0126 (8) | 0.0065 (10) |
C23 | 0.0451 (15) | 0.0601 (18) | 0.0777 (19) | 0.0260 (14) | 0.0231 (14) | 0.0257 (16) |
C7 | 0.0454 (13) | 0.0412 (13) | 0.0443 (13) | 0.0249 (11) | 0.0191 (11) | 0.0187 (11) |
C19 | 0.0442 (14) | 0.0562 (16) | 0.0476 (14) | 0.0297 (13) | 0.0115 (11) | 0.0160 (12) |
C20 | 0.0601 (17) | 0.066 (2) | 0.0509 (16) | 0.0313 (16) | 0.0114 (13) | 0.0073 (14) |
O2 | 0.0433 (11) | 0.124 (2) | 0.0536 (11) | 0.0380 (12) | 0.0153 (9) | 0.0127 (12) |
O4 | 0.0998 (18) | 0.0762 (16) | 0.0925 (17) | 0.0526 (14) | 0.0595 (15) | 0.0127 (13) |
C10 | 0.0561 (17) | 0.077 (2) | 0.0543 (16) | 0.0256 (17) | 0.0137 (14) | 0.0107 (15) |
C17 | 0.0638 (17) | 0.0565 (16) | 0.0459 (14) | 0.0404 (14) | 0.0254 (12) | 0.0171 (12) |
C18 | 0.0535 (15) | 0.0652 (17) | 0.0416 (13) | 0.0415 (14) | 0.0238 (11) | 0.0201 (12) |
C16 | 0.0490 (14) | 0.0590 (16) | 0.0368 (12) | 0.0329 (13) | 0.0142 (11) | 0.0152 (11) |
C26 | 0.085 (2) | 0.0547 (18) | 0.0666 (19) | 0.0336 (17) | 0.0434 (18) | 0.0087 (16) |
O5 | 0.1028 (19) | 0.0788 (17) | 0.0718 (15) | 0.0287 (15) | 0.0355 (14) | −0.0206 (13) |
C24 | 0.0394 (13) | 0.0524 (16) | 0.0566 (15) | 0.0226 (12) | 0.0185 (11) | 0.0143 (13) |
C3 | 0.0470 (14) | 0.0386 (13) | 0.0451 (13) | 0.0229 (11) | 0.0157 (11) | 0.0105 (11) |
C9 | 0.0438 (14) | 0.0573 (16) | 0.0435 (13) | 0.0254 (13) | 0.0177 (11) | 0.0130 (12) |
C14 | 0.0632 (17) | 0.0549 (16) | 0.0604 (16) | 0.0407 (14) | 0.0342 (14) | 0.0215 (13) |
C11 | 0.065 (2) | 0.082 (3) | 0.092 (3) | 0.0233 (19) | 0.0231 (19) | 0.026 (2) |
C12 | 0.0454 (14) | 0.0538 (16) | 0.0454 (13) | 0.0269 (12) | 0.0200 (11) | 0.0071 (12) |
C25 | 0.0497 (15) | 0.0544 (16) | 0.0561 (15) | 0.0286 (13) | 0.0284 (13) | 0.0212 (13) |
C5 | 0.0701 (18) | 0.0612 (18) | 0.0462 (14) | 0.0372 (15) | 0.0302 (13) | 0.0154 (13) |
N6 | 0.0742 (17) | 0.0773 (18) | 0.0840 (18) | 0.0489 (15) | 0.0430 (15) | 0.0210 (15) |
C15 | 0.0577 (16) | 0.0594 (17) | 0.0657 (17) | 0.0365 (14) | 0.0371 (14) | 0.0228 (14) |
O1 | 0.0606 (15) | 0.167 (3) | 0.0615 (15) | 0.0483 (17) | 0.0000 (12) | −0.0188 (16) |
C21 | 0.0578 (19) | 0.056 (2) | 0.083 (2) | 0.0224 (16) | 0.0038 (17) | −0.0044 (17) |
C1 | 0.0463 (17) | 0.103 (3) | 0.080 (2) | 0.0350 (18) | 0.0241 (15) | 0.018 (2) |
C22 | 0.0520 (18) | 0.055 (2) | 0.102 (3) | 0.0182 (15) | 0.0180 (18) | 0.0210 (19) |
O12 | 0.140 (3) | 0.168 (4) | 0.0779 (19) | 0.083 (3) | 0.036 (2) | 0.029 (2) |
O11 | 0.254 (5) | 0.171 (4) | 0.086 (2) | 0.140 (4) | −0.012 (3) | −0.009 (2) |
C55 | 0.154 (5) | 0.068 (3) | 0.065 (2) | 0.047 (3) | 0.002 (3) | 0.015 (2) |
C56 | 0.106 (4) | 0.123 (4) | 0.113 (4) | 0.043 (3) | 0.021 (3) | 0.053 (3) |
C53 | 0.157 (6) | 0.219 (8) | 0.154 (5) | 0.149 (6) | 0.054 (5) | 0.034 (5) |
C54 | 0.221 (8) | 0.181 (7) | 0.127 (5) | 0.102 (7) | 0.081 (6) | 0.015 (5) |
Geometric parameters (Å, º) top
N4—C34 | 1.310 (3) | N2—C7 | 1.389 (3) |
N4—C32 | 1.400 (3) | C8—C3 | 1.408 (4) |
C32—C31 | 1.404 (3) | C8—N1 | 1.412 (3) |
C32—C33 | 1.412 (3) | C8—C7 | 1.420 (3) |
C33—C28 | 1.404 (4) | C13—C18 | 1.388 (4) |
C33—N3 | 1.413 (3) | C13—C14 | 1.400 (3) |
N3—C34 | 1.368 (3) | C13—C12 | 1.524 (4) |
N3—C37 | 1.458 (3) | N5—C25 | 1.357 (4) |
O8—C34 | 1.345 (3) | N5—C26 | 1.380 (4) |
O8—C35 | 1.456 (4) | N5—H5A | 1.00 (3) |
C28—C29 | 1.409 (3) | C2—O1 | 1.193 (3) |
C28—C52 | 1.505 (4) | C2—O2 | 1.313 (3) |
C31—C30 | 1.373 (4) | C2—C3 | 1.495 (4) |
C31—H31 | 0.9300 | N1—C9 | 1.359 (3) |
N7—C50 | 1.367 (4) | N1—C12 | 1.476 (3) |
N7—C51 | 1.380 (4) | O3—C9 | 1.335 (3) |
N7—H7 | 0.90 (4) | O3—C10 | 1.450 (4) |
O7—C52 | 1.337 (3) | C23—C22 | 1.399 (5) |
O7—C27 | 1.456 (4) | C23—C24 | 1.411 (4) |
C42—C41 | 1.393 (4) | C23—H23 | 0.9300 |
C42—C43 | 1.398 (3) | C19—C20 | 1.407 (4) |
C42—H42 | 0.9300 | C19—C24 | 1.416 (4) |
C37—C38 | 1.526 (3) | C19—C16 | 1.496 (4) |
C37—H37A | 0.9700 | C20—C21 | 1.392 (5) |
C37—H37B | 0.9700 | C20—H20 | 0.9300 |
C43—C38 | 1.376 (4) | O2—C1 | 1.445 (4) |
C43—H43 | 0.9300 | O4—C26 | 1.359 (4) |
C48—C47 | 1.379 (5) | O4—N6 | 1.454 (4) |
C48—C49 | 1.402 (4) | C10—C11 | 1.465 (6) |
C48—H48 | 0.9300 | C10—H10A | 0.9700 |
N8—C50 | 1.288 (4) | C10—H10B | 0.9700 |
N8—O10 | 1.454 (4) | C17—C18 | 1.383 (4) |
C38—C39 | 1.388 (3) | C17—C16 | 1.396 (4) |
C51—O9 | 1.219 (4) | C17—H17 | 0.9300 |
C51—O10 | 1.352 (4) | C18—H18 | 0.9300 |
C30—C29 | 1.403 (4) | C16—C15 | 1.407 (4) |
C30—H30 | 0.9300 | C26—O5 | 1.206 (4) |
C47—C46 | 1.388 (5) | C24—C25 | 1.490 (4) |
C47—H47 | 0.9300 | C14—C15 | 1.394 (4) |
C41—C40 | 1.384 (4) | C14—H14 | 0.9300 |
C41—C44 | 1.504 (3) | C11—H11A | 0.9600 |
O6—C52 | 1.201 (3) | C11—H11B | 0.9600 |
C49—C44 | 1.407 (4) | C11—H11C | 0.9600 |
C49—C50 | 1.487 (4) | C12—H12A | 0.9700 |
C44—C45 | 1.400 (4) | C12—H12B | 0.9700 |
C40—C39 | 1.389 (4) | C25—N6 | 1.298 (4) |
C40—H40 | 0.9300 | C5—H5 | 0.9300 |
C39—H39 | 0.9300 | C15—H15 | 0.9300 |
C29—H29 | 0.9300 | C21—C22 | 1.373 (5) |
C45—C46 | 1.388 (4) | C21—H21 | 0.9300 |
C45—H45 | 0.9300 | C1—H1A | 0.9600 |
C27—H27A | 0.9600 | C1—H1B | 0.9600 |
C27—H27B | 0.9600 | C1—H1C | 0.9600 |
C27—H27C | 0.9600 | C22—H22 | 0.9300 |
C46—H46 | 0.9300 | O12—C55 | 1.336 (6) |
C36—C35 | 1.485 (5) | O12—C54 | 1.478 (8) |
C36—H36A | 0.9600 | O11—C55 | 1.164 (5) |
C36—H36B | 0.9600 | C55—C56 | 1.474 (8) |
C36—H36C | 0.9600 | C56—H56A | 0.9600 |
C35—H35A | 0.9700 | C56—H56B | 0.9600 |
C35—H35B | 0.9700 | C56—H56C | 0.9600 |
C6—C5 | 1.387 (4) | C53—C54 | 1.403 (9) |
C6—C7 | 1.406 (4) | C53—H53A | 0.9600 |
C6—H6A | 0.9300 | C53—H53B | 0.9600 |
C4—C5 | 1.367 (4) | C53—H53C | 0.9600 |
C4—C3 | 1.416 (4) | C54—H54A | 0.9700 |
C4—H4 | 0.9300 | C54—H54B | 0.9700 |
N2—C9 | 1.318 (3) | | |
| | | |
C34—N4—C32 | 104.0 (2) | C18—C13—C12 | 123.8 (2) |
N4—C32—C31 | 129.7 (2) | C14—C13—C12 | 118.3 (2) |
N4—C32—C33 | 110.76 (19) | C25—N5—C26 | 108.1 (3) |
C31—C32—C33 | 119.5 (2) | C25—N5—H5A | 126.5 (16) |
C28—C33—C32 | 121.6 (2) | C26—N5—H5A | 125.4 (17) |
C28—C33—N3 | 134.1 (2) | O1—C2—O2 | 122.1 (3) |
C32—C33—N3 | 104.3 (2) | O1—C2—C3 | 124.0 (3) |
C34—N3—C33 | 105.87 (19) | O2—C2—C3 | 113.9 (2) |
C34—N3—C37 | 123.7 (2) | C9—N1—C8 | 106.07 (19) |
C33—N3—C37 | 129.9 (2) | C9—N1—C12 | 121.2 (2) |
C34—O8—C35 | 116.7 (2) | C8—N1—C12 | 132.5 (2) |
C33—C28—C29 | 117.4 (2) | C9—O3—C10 | 118.6 (2) |
C33—C28—C52 | 124.0 (2) | C22—C23—C24 | 120.0 (3) |
C29—C28—C52 | 118.2 (2) | C22—C23—H23 | 120.0 |
C30—C31—C32 | 119.2 (2) | C24—C23—H23 | 120.0 |
C30—C31—H31 | 120.4 | N2—C7—C6 | 127.0 (2) |
C32—C31—H31 | 120.4 | N2—C7—C8 | 111.1 (2) |
C50—N7—C51 | 108.3 (2) | C6—C7—C8 | 121.9 (2) |
C50—N7—H7 | 129 (2) | C20—C19—C24 | 116.7 (3) |
C51—N7—H7 | 122 (2) | C20—C19—C16 | 119.8 (2) |
C52—O7—C27 | 115.1 (2) | C24—C19—C16 | 123.4 (2) |
C41—C42—C43 | 120.5 (2) | C21—C20—C19 | 122.6 (3) |
C41—C42—H42 | 119.7 | C21—C20—H20 | 118.7 |
C43—C42—H42 | 119.7 | C19—C20—H20 | 118.7 |
N3—C37—C38 | 113.43 (18) | C2—O2—C1 | 118.2 (2) |
N3—C37—H37A | 108.9 | C26—O4—N6 | 109.2 (2) |
C38—C37—H37A | 108.9 | O3—C10—C11 | 108.5 (3) |
N3—C37—H37B | 108.9 | O3—C10—H10A | 110.0 |
C38—C37—H37B | 108.9 | C11—C10—H10A | 110.0 |
H37A—C37—H37B | 107.7 | O3—C10—H10B | 110.0 |
C38—C43—C42 | 121.1 (2) | C11—C10—H10B | 110.0 |
C38—C43—H43 | 119.5 | H10A—C10—H10B | 108.4 |
C42—C43—H43 | 119.5 | C18—C17—C16 | 121.8 (3) |
C47—C48—C49 | 121.1 (3) | C18—C17—H17 | 119.1 |
C47—C48—H48 | 119.4 | C16—C17—H17 | 119.1 |
C49—C48—H48 | 119.4 | C17—C18—C13 | 121.2 (2) |
C50—N8—O10 | 104.1 (3) | C17—C18—H18 | 119.4 |
C43—C38—C39 | 118.3 (2) | C13—C18—H18 | 119.4 |
C43—C38—C37 | 121.8 (2) | C17—C16—C15 | 117.1 (2) |
C39—C38—C37 | 119.8 (2) | C17—C16—C19 | 120.7 (3) |
O9—C51—O10 | 124.3 (3) | C15—C16—C19 | 122.0 (2) |
O9—C51—N7 | 130.4 (3) | O5—C26—O4 | 123.2 (3) |
O10—C51—N7 | 105.3 (3) | O5—C26—N5 | 131.0 (3) |
C31—C30—C29 | 121.6 (2) | O4—C26—N5 | 105.8 (3) |
C31—C30—H30 | 119.2 | C23—C24—C19 | 120.7 (3) |
C29—C30—H30 | 119.2 | C23—C24—C25 | 116.2 (2) |
C48—C47—C46 | 119.0 (3) | C19—C24—C25 | 122.9 (2) |
C48—C47—H47 | 120.5 | C8—C3—C4 | 116.5 (2) |
C46—C47—H47 | 120.5 | C8—C3—C2 | 129.0 (2) |
C40—C41—C42 | 118.1 (2) | C4—C3—C2 | 114.5 (2) |
C40—C41—C44 | 121.5 (2) | N2—C9—O3 | 128.1 (2) |
C42—C41—C44 | 120.3 (2) | N2—C9—N1 | 115.2 (2) |
N4—C34—O8 | 127.7 (3) | O3—C9—N1 | 116.7 (2) |
N4—C34—N3 | 115.0 (2) | C15—C14—C13 | 120.9 (3) |
O8—C34—N3 | 117.2 (2) | C15—C14—H14 | 119.5 |
C48—C49—C44 | 120.2 (3) | C13—C14—H14 | 119.5 |
C48—C49—C50 | 118.1 (2) | C10—C11—H11A | 109.5 |
C44—C49—C50 | 121.4 (2) | C10—C11—H11B | 109.5 |
O6—C52—O7 | 123.9 (3) | H11A—C11—H11B | 109.5 |
O6—C52—C28 | 123.6 (2) | C10—C11—H11C | 109.5 |
O7—C52—C28 | 112.5 (2) | H11A—C11—H11C | 109.5 |
N8—C50—N7 | 112.5 (3) | H11B—C11—H11C | 109.5 |
N8—C50—C49 | 123.6 (3) | N1—C12—C13 | 114.3 (2) |
N7—C50—C49 | 123.8 (2) | N1—C12—H12A | 108.7 |
C45—C44—C49 | 117.7 (2) | C13—C12—H12A | 108.7 |
C45—C44—C41 | 119.2 (2) | N1—C12—H12B | 108.7 |
C49—C44—C41 | 123.1 (2) | C13—C12—H12B | 108.7 |
C41—C40—C39 | 121.0 (2) | H12A—C12—H12B | 107.6 |
C41—C40—H40 | 119.5 | N6—C25—N5 | 112.9 (3) |
C39—C40—H40 | 119.5 | N6—C25—C24 | 123.1 (3) |
C51—O10—N8 | 109.8 (2) | N5—C25—C24 | 123.9 (2) |
C38—C39—C40 | 120.9 (2) | C4—C5—C6 | 120.4 (2) |
C38—C39—H39 | 119.5 | C4—C5—H5 | 119.8 |
C40—C39—H39 | 119.5 | C6—C5—H5 | 119.8 |
C30—C29—C28 | 120.6 (2) | C25—N6—O4 | 104.0 (2) |
C30—C29—H29 | 119.7 | C14—C15—C16 | 121.0 (2) |
C28—C29—H29 | 119.7 | C14—C15—H15 | 119.5 |
C46—C45—C44 | 121.4 (3) | C16—C15—H15 | 119.5 |
C46—C45—H45 | 119.3 | C22—C21—C20 | 119.8 (3) |
C44—C45—H45 | 119.3 | C22—C21—H21 | 120.1 |
O7—C27—H27A | 109.5 | C20—C21—H21 | 120.1 |
O7—C27—H27B | 109.5 | O2—C1—H1A | 109.5 |
H27A—C27—H27B | 109.5 | O2—C1—H1B | 109.5 |
O7—C27—H27C | 109.5 | H1A—C1—H1B | 109.5 |
H27A—C27—H27C | 109.5 | O2—C1—H1C | 109.5 |
H27B—C27—H27C | 109.5 | H1A—C1—H1C | 109.5 |
C45—C46—C47 | 120.5 (3) | H1B—C1—H1C | 109.5 |
C45—C46—H46 | 119.7 | C21—C22—C23 | 120.2 (3) |
C47—C46—H46 | 119.7 | C21—C22—H22 | 119.9 |
C35—C36—H36A | 109.5 | C23—C22—H22 | 119.9 |
C35—C36—H36B | 109.5 | C55—O12—C54 | 119.6 (5) |
H36A—C36—H36B | 109.5 | O11—C55—O12 | 121.7 (6) |
C35—C36—H36C | 109.5 | O11—C55—C56 | 125.8 (6) |
H36A—C36—H36C | 109.5 | O12—C55—C56 | 112.1 (4) |
H36B—C36—H36C | 109.5 | C55—C56—H56A | 109.5 |
O8—C35—C36 | 109.0 (3) | C55—C56—H56B | 109.5 |
O8—C35—H35A | 109.9 | H56A—C56—H56B | 109.5 |
C36—C35—H35A | 109.9 | C55—C56—H56C | 109.5 |
O8—C35—H35B | 109.9 | H56A—C56—H56C | 109.5 |
C36—C35—H35B | 109.9 | H56B—C56—H56C | 109.5 |
H35A—C35—H35B | 108.3 | C54—C53—H53A | 109.5 |
C5—C6—C7 | 118.0 (2) | C54—C53—H53B | 109.5 |
C5—C6—H6A | 121.0 | H53A—C53—H53B | 109.5 |
C7—C6—H6A | 121.0 | C54—C53—H53C | 109.5 |
C5—C4—C3 | 123.7 (3) | H53A—C53—H53C | 109.5 |
C5—C4—H4 | 118.1 | H53B—C53—H53C | 109.5 |
C3—C4—H4 | 118.1 | C53—C54—O12 | 109.4 (6) |
C9—N2—C7 | 103.8 (2) | C53—C54—H54A | 109.8 |
C3—C8—N1 | 136.7 (2) | O12—C54—H54A | 109.8 |
C3—C8—C7 | 119.5 (2) | C53—C54—H54B | 109.8 |
N1—C8—C7 | 103.9 (2) | O12—C54—H54B | 109.8 |
C18—C13—C14 | 117.9 (2) | H54A—C54—H54B | 108.2 |
| | | |
C34—N4—C32—C31 | 180.0 (2) | C3—C8—N1—C12 | 5.7 (5) |
C34—N4—C32—C33 | 1.3 (2) | C7—C8—N1—C12 | −175.2 (3) |
N4—C32—C33—C28 | −179.2 (2) | C9—N2—C7—C6 | −178.2 (3) |
C31—C32—C33—C28 | 2.0 (3) | C9—N2—C7—C8 | 0.2 (3) |
N4—C32—C33—N3 | −0.6 (2) | C5—C6—C7—N2 | 178.0 (3) |
C31—C32—C33—N3 | −179.5 (2) | C5—C6—C7—C8 | −0.2 (4) |
C28—C33—N3—C34 | 178.0 (2) | C3—C8—C7—N2 | 179.9 (2) |
C32—C33—N3—C34 | −0.3 (2) | N1—C8—C7—N2 | 0.6 (3) |
C28—C33—N3—C37 | 6.6 (4) | C3—C8—C7—C6 | −1.6 (4) |
C32—C33—N3—C37 | −171.7 (2) | N1—C8—C7—C6 | 179.1 (2) |
C32—C33—C28—C29 | 0.2 (3) | C24—C19—C20—C21 | −1.5 (5) |
N3—C33—C28—C29 | −177.9 (2) | C16—C19—C20—C21 | 177.8 (3) |
C32—C33—C28—C52 | −172.4 (2) | O1—C2—O2—C1 | −1.0 (5) |
N3—C33—C28—C52 | 9.5 (4) | C3—C2—O2—C1 | −179.5 (3) |
N4—C32—C31—C30 | 177.6 (2) | C9—O3—C10—C11 | 93.9 (3) |
C33—C32—C31—C30 | −3.8 (3) | C16—C17—C18—C13 | −0.4 (4) |
C34—N3—C37—C38 | −99.7 (3) | C14—C13—C18—C17 | −0.3 (4) |
C33—N3—C37—C38 | 70.3 (3) | C12—C13—C18—C17 | 176.6 (2) |
C41—C42—C43—C38 | −0.5 (4) | C18—C17—C16—C15 | 1.1 (4) |
C42—C43—C38—C39 | −1.0 (4) | C18—C17—C16—C19 | −174.4 (2) |
C42—C43—C38—C37 | 176.4 (2) | C20—C19—C16—C17 | 41.4 (4) |
N3—C37—C38—C43 | 23.8 (3) | C24—C19—C16—C17 | −139.3 (3) |
N3—C37—C38—C39 | −158.9 (2) | C20—C19—C16—C15 | −133.8 (3) |
C50—N7—C51—O9 | 177.4 (3) | C24—C19—C16—C15 | 45.4 (4) |
C50—N7—C51—O10 | 0.1 (3) | N6—O4—C26—O5 | 179.7 (3) |
C32—C31—C30—C29 | 3.6 (4) | N6—O4—C26—N5 | −0.9 (3) |
C49—C48—C47—C46 | 0.8 (5) | C25—N5—C26—O5 | −178.9 (4) |
C43—C42—C41—C40 | 1.3 (4) | C25—N5—C26—O4 | 1.8 (3) |
C43—C42—C41—C44 | 177.9 (2) | C22—C23—C24—C19 | 0.2 (4) |
C32—N4—C34—O8 | 175.5 (2) | C22—C23—C24—C25 | 175.9 (3) |
C32—N4—C34—N3 | −1.6 (3) | C20—C19—C24—C23 | 1.5 (4) |
C35—O8—C34—N4 | 2.0 (4) | C16—C19—C24—C23 | −177.8 (3) |
C35—O8—C34—N3 | 179.0 (2) | C20—C19—C24—C25 | −174.0 (3) |
C33—N3—C34—N4 | 1.2 (3) | C16—C19—C24—C25 | 6.7 (4) |
C37—N3—C34—N4 | 173.32 (19) | N1—C8—C3—C4 | −179.2 (3) |
C33—N3—C34—O8 | −176.2 (2) | C7—C8—C3—C4 | 1.9 (4) |
C37—N3—C34—O8 | −4.1 (3) | N1—C8—C3—C2 | −1.5 (5) |
C47—C48—C49—C44 | 0.7 (5) | C7—C8—C3—C2 | 179.6 (3) |
C47—C48—C49—C50 | −173.5 (3) | C5—C4—C3—C8 | −0.4 (4) |
C27—O7—C52—O6 | −4.3 (4) | C5—C4—C3—C2 | −178.5 (3) |
C27—O7—C52—C28 | 176.3 (2) | O1—C2—C3—C8 | −172.0 (3) |
C33—C28—C52—O6 | 30.0 (4) | O2—C2—C3—C8 | 6.5 (4) |
C29—C28—C52—O6 | −142.6 (3) | O1—C2—C3—C4 | 5.8 (5) |
C33—C28—C52—O7 | −150.6 (2) | O2—C2—C3—C4 | −175.8 (3) |
C29—C28—C52—O7 | 36.8 (3) | C7—N2—C9—O3 | 179.3 (3) |
O10—N8—C50—N7 | 0.4 (3) | C7—N2—C9—N1 | −1.1 (3) |
O10—N8—C50—C49 | 176.6 (2) | C10—O3—C9—N2 | −8.4 (5) |
C51—N7—C50—N8 | −0.3 (3) | C10—O3—C9—N1 | 172.0 (3) |
C51—N7—C50—C49 | −176.5 (2) | C8—N1—C9—N2 | 1.5 (3) |
C48—C49—C50—N8 | −58.7 (4) | C12—N1—C9—N2 | 176.4 (2) |
C44—C49—C50—N8 | 127.2 (3) | C8—N1—C9—O3 | −178.8 (2) |
C48—C49—C50—N7 | 117.1 (3) | C12—N1—C9—O3 | −3.9 (4) |
C44—C49—C50—N7 | −57.0 (4) | C18—C13—C14—C15 | 0.3 (4) |
C48—C49—C44—C45 | −1.7 (4) | C12—C13—C14—C15 | −176.8 (2) |
C50—C49—C44—C45 | 172.3 (3) | C9—N1—C12—C13 | 102.2 (3) |
C48—C49—C44—C41 | 176.1 (3) | C8—N1—C12—C13 | −84.5 (3) |
C50—C49—C44—C41 | −9.9 (4) | C18—C13—C12—N1 | −1.5 (4) |
C40—C41—C44—C45 | 126.8 (3) | C14—C13—C12—N1 | 175.4 (2) |
C42—C41—C44—C45 | −49.7 (4) | C26—N5—C25—N6 | −2.1 (3) |
C40—C41—C44—C49 | −50.9 (4) | C26—N5—C25—C24 | 174.1 (3) |
C42—C41—C44—C49 | 132.6 (3) | C23—C24—C25—N6 | 58.8 (4) |
C42—C41—C40—C39 | −0.6 (4) | C19—C24—C25—N6 | −125.5 (3) |
C44—C41—C40—C39 | −177.2 (3) | C23—C24—C25—N5 | −117.0 (3) |
O9—C51—O10—N8 | −177.4 (3) | C19—C24—C25—N5 | 58.7 (4) |
N7—C51—O10—N8 | 0.1 (3) | C3—C4—C5—C6 | −1.5 (5) |
C50—N8—O10—C51 | −0.3 (3) | C7—C6—C5—C4 | 1.8 (4) |
C43—C38—C39—C40 | 1.7 (4) | N5—C25—N6—O4 | 1.4 (3) |
C37—C38—C39—C40 | −175.7 (3) | C24—C25—N6—O4 | −174.8 (3) |
C41—C40—C39—C38 | −0.9 (4) | C26—O4—N6—C25 | −0.3 (3) |
C31—C30—C29—C28 | −1.4 (4) | C13—C14—C15—C16 | 0.4 (4) |
C33—C28—C29—C30 | −0.5 (3) | C17—C16—C15—C14 | −1.1 (4) |
C52—C28—C29—C30 | 172.6 (2) | C19—C16—C15—C14 | 174.4 (3) |
C49—C44—C45—C46 | 1.3 (5) | C19—C20—C21—C22 | −0.2 (5) |
C41—C44—C45—C46 | −176.6 (3) | C20—C21—C22—C23 | 1.9 (5) |
C44—C45—C46—C47 | 0.2 (5) | C24—C23—C22—C21 | −1.9 (5) |
C48—C47—C46—C45 | −1.2 (5) | C54—O12—C55—O11 | 5.9 (8) |
C34—O8—C35—C36 | −174.6 (3) | C54—O12—C55—C56 | 179.2 (6) |
C3—C8—N1—C9 | 179.8 (3) | C55—O12—C54—C53 | −140.9 (6) |
C7—C8—N1—C9 | −1.2 (3) | | |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N5—H5A···N4i | 1.01 | 1.85 | 2.862 (3) | 176 |
N7—H7···N2i | 0.90 | 2.01 | 2.905 (3) | 173 |
C12—H12A···O5ii | 0.97 | 2.58 | 3.421 (4) | 145 |
C30—H30···O9iii | 0.93 | 2.58 | 3.484 (3) | 163 |
Symmetry codes: (i) −x, −y+1, −z+1; (ii) −x, −y, −z+1; (iii) x−1, y−1, z. |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N5—H5A···N4i | 1.01 | 1.85 | 2.862 (3) | 176 |
N7—H7···N2i | 0.90 | 2.01 | 2.905 (3) | 173 |
C12—H12A···O5ii | 0.97 | 2.58 | 3.421 (4) | 145 |
C30—H30···O9iii | 0.93 | 2.58 | 3.484 (3) | 163 |
Symmetry codes: (i) −x, −y+1, −z+1; (ii) −x, −y, −z+1; (iii) x−1, y−1, z. |
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 π–π 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.