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Acta Crystallogr Sect E Struct Rep Online. 2010 August 1; 66(Pt 8): o1907–o1908.
Published online 2010 July 3. doi:  10.1107/S1600536810025262
PMCID: PMC3007271

(2S)-2-(4-Ethyl-2,3-dioxopiperazine-1-carboxamido)-2-(4-hy­droxy­phen­yl)acetic acid

Abstract

There are two mol­ecules in the asymmetric unit of the title compound, C15H17N3O6. The 2,3-dioxopiperazine ring adopts a half-chair conformation with torsion angles of −7.6 (4) and 35.1 (4)° in one mol­ecule, and 5.3 (4) and 45.4 (4)° in the other mol­ecule. In the crystal structure, the carb­oxy groups are involved in classical inversion-related O—H(...)O hydrogen bonds, which link the mol­ecules into centrosymmetric dimers. These dimers are further linked by inter­molecular O—H(...)O and C—H(...)O hydrogen bonds. Each independent mol­ecule also exhibits an intra­molecular N—H(...)O hydrogen bond. The H atoms of the carb­oxy groups are disordered over two positions, with refined site-occupancy factors of 0.5.

Related literature

For general background to cefoperazone, a third generation cephalosporin anti­biotic, and HO-EPCP [(2R)-2-(4-ethyl-2,3-dioxopiperazine-1-carboxamido)-2-(4-hydroxyphenyl)acetic acid], which has been investigated extensively as a key inter­mediate for the synthesis of cefoperazone, see: Spyker et al. (1985 [triangle]); Chen et al. (2009 [triangle]); Murakami et al. (1981 [triangle]); Albrecht et al. (1991 [triangle]). For the synthesis of the (2S)-enantiomer of (HO-EPCP), see: De Lorenzi et al. (2001 [triangle]). For a related structure, see: Lenstra et al. (1998 [triangle]). For disordered carb­oxy dimers, see: Leiserowitz (1976 [triangle]); Feeder & Jones (1996 [triangle]). For helical chains, see: Adachi et al. (2001 [triangle]); Xu et al.(2003 [triangle]); Enamullah et al. (2006 [triangle]). For hydrogen-bond motifs, see: Bernstein et al. (1995 [triangle]). For the synthesis, see: Saikawa et al. (1978 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-66-o1907-scheme1.jpg

Experimental

Crystal data

  • C15H17N3O6
  • M r = 335.32
  • Orthorhombic, An external file that holds a picture, illustration, etc.
Object name is e-66-o1907-efi9.jpg
  • a = 11.5899 (19) Å
  • b = 13.038 (2) Å
  • c = 20.794 (3) Å
  • V = 3142.2 (9) Å3
  • Z = 8
  • Mo Kα radiation
  • μ = 0.11 mm−1
  • T = 298 K
  • 0.51 × 0.15 × 0.09 mm

Data collection

  • Bruker SMART CCD area-detector diffractometer
  • 16467 measured reflections
  • 3237 independent reflections
  • 2722 reflections with I > 2σ(I)
  • R int = 0.040

Refinement

  • R[F 2 > 2σ(F 2)] = 0.044
  • wR(F 2) = 0.107
  • S = 1.06
  • 3237 reflections
  • 449 parameters
  • 16 restraints
  • H atoms treated by a mixture of independent and constrained refinement
  • Δρmax = 0.18 e Å−3
  • Δρmin = −0.16 e Å−3

Data collection: SMART (Bruker, 1999 [triangle]); cell refinement: SAINT (Bruker, 1999 [triangle]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: SHELXTL (Sheldrick, 2008 [triangle]); software used to prepare material for publication: SHELXTL.

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810025262/lx2155sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810025262/lx2155Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Acknowledgments

Financial support from the National Natural Science Foundation of China (grant No. 20572064) and the Natural Science Foundation of Shandong Province, China (grant No. Y2006B30) is gratefully acknowledged.

supplementary crystallographic information

Comment

Among enantiomers of 2-(4-ethyl-3-dioxo-1-piperazinyl)carboxamido]-2-(4-hydroxyphenyl)acetic acid, its (2R)-enantiomer (HO-EPCP) has been extensively investigated as a key intermediate for the synthesis of cefoperazone (Murakami et al., 1981; Albrecht et al., 1991), which is a third generation cephalosporin antibiotic (Spyker et al., 1985; Chen et al., 2009), whereas its (2S)-enantiomer was presented only one time as a chiral compound of pharmaceutical interest evaluated for enantiorecognition (De Lorenzi et al., 2001). Now we report the crystal structure of the title compound which crystallizes with two unique molecules, denoted as A & B, in the asymmetric unit (Fig. 1).

The two molecules (A and B) are linked into a dimer through classical inversion-related O—H···O hydrogen bonds (Table 1) between the carboxy groups of A and B, where the H atoms of the carboxy groups are disordered over two positions, with refined site-occupancy factors of 0.5 and 0.5. The disordered model for the carboxy group may be ascribed to the requirement of intermolecular forces (Leiserowitz, 1976; Feeder et al., 1996). Both molecules possess similar geometric parameters except for the slight differences in some bond lenghths and angles. The 2,3-dioxopiperazine ring adopts a half-chair conformation with torsion angles of -7.6 (4) and 35.1 (4)° in A, while 5.3 (4) and 45.4 (4)° in B, similar to those of -3.3 (4) and 38.6 (4)° reported previously for the related molecule 2,3-diketopiperazine (Lenstra et al., 1998). The dihedral angle between the two benzene rings belonging to A and B in the dimer is 47.32 (10)°. The intramolecular N3—H3···O2 and N6—H6D···O8 hydrogen bonds exist (Table 1) and create an R(6) ring motif (Bernstein et al., 1995) in either molecule.

The packing of the title compound is obviously stabilized by the intermolecular O—H···O and C—H···O hydrogen bonds. For the molecule A, an infinite one-dimensional helix chain (Adachi et al. 2001; Xu et al. 2003) is formed by a combination of the intermolecular O—H···O and C—H···O hydrogen bonds (Fig. 2), locally giving an R22(9) ring motif (Bernstein et al., 1995). This motif arises from atoms O6—H6 and C12—H12 in the molecule at (x, y, z), which act as hydrogen-bond donors, to atoms O1 and O2 in the neighboring molecule at (x + 1/2, -y + 1/2, -z + 1). For the molecule B, the same infinite one-dimensional helix chain is generated through a combination of the intermolecular O12—H12A···O7ii and C27—H27···O8ii [symmetry code: (ii) x + 1/2, -y + 5/2, -z + 1] hydrogen bonds. Finally, the helix chains of both molecules are alternatively linked by the interchain O—H···O hydrogen bonds to produce a two-dimensional network (Fig. 3) in the ab plane. Such helix chains of the title molecule may be significant in simulating of the life system.

Experimental

The title compound was obtained as a white solid in 80% yield by a similar method used for the synthesis of its (2R)-enantiomer (Saikawa et al., 1978). 1H NMR (300 MHz, DMSO-d6): δ 9.68 (d, 1H, J = 6.42 Hz), 9.58 (s, 1H), 7.18 (d, 2H, J = 8.27 Hz), 6.77 (d, 2H, J = 8.27 Hz), 5.20 (d, 1H, J = 6.44 Hz), 3.90 (br, 2H), 3.56 (br, 2H), 3.40 (m, 2H), 1.08 (t, 3H, J = 7.06 Hz). Single crystals of the title compound suitable for X-ray diffraction analysis were obtained by slow cooling of a hot solution in H2O.

Refinement

Hydrogen atoms attached to refined atoms were placed in geometrically idealized positions and refined using a riding model, with C—H = 0.93, 0.97 and 0.96 Å for aromatic, methylene and methyl H, respectively, and Uiso(H) = 1.5Ueq(C) for methyl H, and Uiso(H) =1.2Ueq(C) for all other H atoms. The H atoms (H4O, H5O, H11O, and H10O) of carboxy groups were located in the different map and refined isotropically subject to an O—H = 0.85 (10) Å distance over two orientations in a 50/50 ratio. These C—O bonds were restrained to be the same within a standard deviation of 0.01 Å, total 16 restrains were used to model the two carboxy groups. In the absence of significant anomalous scattering effects, measured Friedel pairs were merged.

Figures

Fig. 1.
A view of the title compound, showing 30% probability displacement ellipsoids. The disordered moieties (dotted lines) are shown.
Fig. 2.
The hydrogen-bonded one-dimensional helix chain of the molecule A with an R22(9) ring motif viewed along the c axis. The disordered moieties and some hydrogen atoms are omitted for clarity. [Symmetry code: (i) x + 1/2, - y + 1/2, - z + 1].
Fig. 3.
The two-dimensional network of the title compound with R22(8) and R22(9) ring motifs viewed along the c axis. The disordered moieties and some hydrogen atoms are omitted for clarity. [Symmetry codes: (i) x + 1/2, - y + 1/2, - z + 1; (ii) x + 1/2, - y+ ...

Crystal data

C15H17N3O6F(000) = 1408
Mr = 335.32Dx = 1.418 Mg m3
Orthorhombic, P212121Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2abCell parameters from 3149 reflections
a = 11.5899 (19) Åθ = 2.5–22.5°
b = 13.038 (2) ŵ = 0.11 mm1
c = 20.794 (3) ÅT = 298 K
V = 3142.2 (9) Å3Bar, colourless
Z = 80.51 × 0.15 × 0.09 mm

Data collection

Bruker SMART CCD area-detector diffractometer2722 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.040
graphiteθmax = 25.4°, θmin = 1.8°
Detector resolution: 10.0 pixels mm-1h = −13→13
phi and ω scansk = −15→15
16467 measured reflectionsl = −18→25
3237 independent reflections

Refinement

Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.044Hydrogen site location: difference Fourier map
wR(F2) = 0.107H atoms treated by a mixture of independent and constrained refinement
S = 1.06w = 1/[σ2(Fo2) + (0.0613P)2 + 0.0947P] where P = (Fo2 + 2Fc2)/3
3237 reflections(Δ/σ)max < 0.001
449 parametersΔρmax = 0.18 e Å3
16 restraintsΔρmin = −0.16 e Å3

Special details

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 F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > σ(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ 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)

xyzUiso*/UeqOcc. (<1)
O50.6862 (2)0.66654 (17)0.51841 (12)0.0584 (6)
C10.4645 (3)0.3773 (2)0.73859 (14)0.0421 (7)
C20.5301 (3)0.4183 (2)0.67963 (14)0.0379 (7)
C30.6229 (4)0.5339 (3)0.75568 (14)0.0608 (10)
H3A0.56140.58310.76300.073*
H3B0.69600.56960.75980.073*
C40.6161 (3)0.4511 (3)0.80428 (14)0.0515 (8)
H4A0.68150.40520.79940.062*
H4B0.61910.48050.84710.062*
C50.4652 (3)0.3361 (3)0.85232 (14)0.0534 (9)
H5A0.38410.32060.84570.064*
H5B0.47170.37810.89060.064*
C60.5296 (4)0.2396 (3)0.86191 (19)0.0841 (13)
H6A0.49730.20280.89760.126*
H6B0.60910.25490.87050.126*
H6C0.52420.19830.82380.126*
C70.6935 (3)0.5273 (2)0.64418 (14)0.0468 (8)
C80.78013 (16)0.6197 (2)0.52363 (14)0.0420 (7)
C90.7784 (3)0.5059 (2)0.53998 (13)0.0417 (7)
H90.85360.48650.55780.050*
C100.7571 (3)0.4445 (2)0.47940 (13)0.0392 (7)
C110.8371 (3)0.3733 (2)0.45867 (14)0.0445 (8)
H110.90520.36460.48170.053*
C120.8176 (3)0.3146 (2)0.40408 (15)0.0474 (8)
H120.87230.26710.39050.057*
C130.7164 (3)0.3271 (2)0.37011 (14)0.0435 (8)
C140.6354 (3)0.3972 (3)0.39031 (15)0.0507 (8)
H140.56710.40580.36740.061*
C150.6563 (3)0.4549 (2)0.44491 (15)0.0480 (8)
H150.60110.50180.45870.058*
C160.4769 (4)1.2845 (3)0.1574 (2)0.0929 (15)
H16A0.44131.30660.19670.139*
H16B0.44161.31920.12180.139*
H16C0.55771.30030.15850.139*
C170.4611 (3)1.1708 (3)0.14984 (15)0.0552 (9)
H17A0.37941.15480.14950.066*
H17B0.49351.14920.10900.066*
C180.4657 (3)1.1091 (2)0.25917 (14)0.0415 (7)
C190.5391 (3)1.0779 (2)0.31764 (13)0.0379 (7)
C200.6653 (3)0.9982 (3)0.23883 (13)0.0564 (9)
H20A0.61980.93810.22820.068*
H20B0.74620.98060.23440.068*
C210.6363 (3)1.0832 (3)0.19387 (14)0.0535 (9)
H21A0.68671.14120.20200.064*
H21B0.64841.06080.14990.064*
C220.7251 (3)1.0017 (2)0.35317 (14)0.0413 (7)
C230.7895 (3)1.0151 (2)0.46270 (13)0.0400 (7)
H230.86711.03220.44740.048*
C240.78669 (17)0.9022 (2)0.48071 (13)0.0403 (7)
C250.7646 (3)1.0775 (2)0.52265 (13)0.0380 (7)
C260.8464 (3)1.1431 (2)0.54761 (15)0.0450 (7)
H260.91701.15000.52680.054*
C270.8258 (3)1.1987 (2)0.60304 (14)0.0484 (8)
H270.88231.24230.61930.058*
C280.7214 (3)1.1894 (2)0.63420 (14)0.0441 (8)
C290.6382 (3)1.1250 (3)0.60949 (15)0.0540 (9)
H290.56731.11880.63010.065*
C300.6598 (3)1.0695 (2)0.55422 (15)0.0494 (8)
H300.60321.02620.53800.059*
N10.5094 (2)0.39370 (19)0.79653 (11)0.0421 (6)
N20.6125 (2)0.49079 (18)0.69051 (11)0.0448 (6)
N30.6901 (2)0.48256 (18)0.58659 (10)0.0440 (6)
H30.63570.44020.57730.053*
N40.5174 (2)1.11428 (19)0.20220 (11)0.0412 (6)
N50.6415 (2)1.02945 (18)0.30565 (10)0.0402 (6)
N60.7073 (2)1.03845 (17)0.41218 (10)0.0421 (6)
H6D0.64771.07560.42020.051*
O10.3770 (2)0.3277 (2)0.72961 (11)0.0663 (7)
O20.50699 (18)0.38196 (17)0.62759 (9)0.0482 (6)
O30.7594 (2)0.59548 (19)0.65771 (11)0.0759 (9)
O40.8770 (2)0.65925 (18)0.51346 (13)0.0615 (7)
H4O0.900 (8)0.722 (3)0.509 (4)0.092*0.50
H5O0.687 (9)0.726 (3)0.500 (4)0.092*0.50
O60.6918 (2)0.27188 (18)0.31598 (10)0.0590 (6)
H60.74930.24010.30460.088*
O70.3658 (2)1.1346 (2)0.26865 (11)0.0609 (7)
O80.50410 (18)1.10077 (18)0.37060 (9)0.0507 (6)
O90.8068 (2)0.94970 (17)0.33806 (10)0.0625 (7)
O100.8777 (2)0.86393 (17)0.50285 (12)0.0532 (6)
H10O0.881 (7)0.798 (2)0.503 (4)0.080*0.50
O110.6930 (2)0.85492 (17)0.47513 (12)0.0604 (7)
H11O0.679 (8)0.800 (4)0.496 (4)0.091*0.50
O120.6966 (2)1.24064 (19)0.68955 (10)0.0615 (7)
H12A0.75211.27580.70000.092*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
O50.0529 (15)0.0450 (13)0.0772 (16)0.0050 (12)0.0103 (13)0.0107 (12)
C10.0428 (19)0.0438 (17)0.0398 (17)−0.0002 (16)0.0001 (15)−0.0009 (13)
C20.0387 (17)0.0364 (15)0.0386 (17)0.0030 (14)0.0005 (14)0.0016 (13)
C30.085 (3)0.059 (2)0.0387 (18)−0.026 (2)0.0137 (18)−0.0173 (16)
C40.057 (2)0.066 (2)0.0320 (16)−0.0083 (18)0.0017 (15)−0.0093 (15)
C50.057 (2)0.064 (2)0.0388 (17)0.0020 (18)0.0073 (16)0.0106 (15)
C60.115 (4)0.065 (3)0.072 (3)0.010 (3)0.007 (3)0.021 (2)
C70.060 (2)0.0418 (16)0.0389 (17)−0.0105 (17)0.0088 (15)0.0007 (14)
C80.046 (2)0.0422 (16)0.0375 (16)−0.0016 (16)0.0079 (15)0.0004 (13)
C90.0481 (19)0.0394 (15)0.0375 (16)0.0039 (15)0.0048 (14)0.0043 (12)
C100.0469 (19)0.0338 (14)0.0370 (15)0.0008 (13)0.0073 (14)0.0068 (12)
C110.0459 (19)0.0422 (16)0.0454 (17)0.0058 (15)0.0025 (15)0.0069 (14)
C120.051 (2)0.0400 (15)0.0511 (19)0.0093 (15)0.0143 (16)0.0010 (14)
C130.055 (2)0.0370 (15)0.0383 (16)−0.0053 (15)0.0132 (15)−0.0008 (13)
C140.051 (2)0.0588 (19)0.0428 (18)0.0054 (18)0.0011 (15)−0.0040 (16)
C150.050 (2)0.0492 (18)0.0447 (18)0.0147 (16)0.0060 (16)−0.0026 (15)
C160.126 (4)0.071 (3)0.082 (3)0.003 (3)−0.029 (3)0.025 (2)
C170.046 (2)0.081 (2)0.0387 (18)0.0045 (19)−0.0083 (16)0.0017 (17)
C180.044 (2)0.0415 (17)0.0391 (17)−0.0024 (15)−0.0020 (15)−0.0052 (13)
C190.0425 (18)0.0359 (15)0.0353 (16)−0.0011 (14)0.0030 (14)−0.0010 (12)
C200.064 (2)0.069 (2)0.0363 (17)0.026 (2)−0.0042 (16)−0.0180 (16)
C210.047 (2)0.080 (2)0.0333 (17)0.0110 (19)0.0011 (14)−0.0053 (16)
C220.0510 (19)0.0342 (14)0.0387 (16)0.0073 (15)−0.0022 (15)0.0003 (12)
C230.0442 (18)0.0400 (15)0.0357 (15)−0.0017 (14)−0.0033 (13)0.0050 (12)
C240.0473 (19)0.0417 (15)0.0319 (15)−0.0015 (16)−0.0054 (14)−0.0003 (12)
C250.0423 (18)0.0354 (14)0.0364 (15)0.0009 (13)−0.0058 (14)0.0050 (12)
C260.0423 (19)0.0475 (17)0.0453 (17)−0.0079 (15)0.0012 (14)0.0069 (14)
C270.051 (2)0.0456 (17)0.0486 (18)−0.0088 (16)−0.0108 (16)−0.0060 (14)
C280.049 (2)0.0426 (15)0.0408 (17)0.0048 (16)−0.0101 (15)0.0007 (13)
C290.049 (2)0.065 (2)0.0489 (19)−0.0050 (19)0.0057 (16)−0.0076 (16)
C300.047 (2)0.0521 (19)0.0492 (19)−0.0146 (16)−0.0025 (16)−0.0068 (15)
N10.0449 (16)0.0437 (13)0.0377 (13)0.0032 (12)0.0022 (12)0.0041 (11)
N20.0634 (18)0.0390 (13)0.0320 (13)−0.0106 (13)0.0090 (12)−0.0028 (11)
N30.0565 (17)0.0417 (13)0.0339 (13)−0.0120 (13)0.0062 (12)0.0009 (11)
N40.0406 (15)0.0501 (14)0.0330 (13)0.0015 (12)−0.0020 (11)−0.0019 (11)
N50.0478 (16)0.0409 (13)0.0318 (12)0.0108 (12)−0.0036 (11)−0.0057 (10)
N60.0526 (17)0.0398 (13)0.0339 (13)0.0080 (13)−0.0028 (12)0.0020 (11)
O10.0525 (16)0.0900 (18)0.0564 (15)−0.0224 (15)−0.0003 (12)0.0063 (14)
O20.0522 (14)0.0569 (13)0.0355 (12)−0.0080 (11)−0.0067 (10)−0.0026 (10)
O30.099 (2)0.0766 (16)0.0520 (14)−0.0526 (17)0.0165 (14)−0.0137 (13)
O40.0525 (16)0.0522 (14)0.0799 (17)−0.0074 (13)0.0115 (13)0.0142 (13)
O60.0652 (16)0.0586 (14)0.0530 (14)−0.0088 (13)0.0116 (12)−0.0176 (11)
O70.0371 (14)0.0910 (18)0.0545 (14)0.0106 (13)0.0005 (11)−0.0080 (13)
O80.0486 (14)0.0694 (14)0.0341 (12)0.0074 (12)0.0080 (10)0.0019 (10)
O90.0718 (17)0.0650 (15)0.0508 (13)0.0346 (14)−0.0129 (12)−0.0133 (11)
O100.0516 (14)0.0462 (12)0.0619 (14)0.0026 (12)−0.0150 (11)0.0048 (11)
O110.0536 (15)0.0461 (12)0.0816 (18)−0.0110 (12)−0.0200 (14)0.0137 (12)
O120.0635 (17)0.0705 (16)0.0504 (13)0.0077 (14)−0.0068 (12)−0.0234 (12)

Geometric parameters (Å, °)

O5—C81.2534 (17)C16—H16C0.9600
O5—O103.414 (3)C17—N41.468 (4)
O5—H5O0.86 (3)C17—H17A0.9700
C1—O11.217 (4)C17—H17B0.9700
C1—N11.330 (4)C18—O71.221 (4)
C1—C21.539 (4)C18—N41.329 (4)
C2—O21.211 (3)C18—C191.539 (4)
C2—N21.362 (4)C19—O81.211 (3)
C3—N21.472 (4)C19—N51.367 (4)
C3—C41.482 (5)C20—N51.474 (3)
C3—H3A0.9700C20—C211.488 (4)
C3—H3B0.9700C20—H20A0.9700
C4—N11.454 (4)C20—H20B0.9700
C4—H4A0.9700C21—N41.447 (4)
C4—H4B0.9700C21—H21A0.9700
C5—N11.474 (4)C21—H21B0.9700
C5—C61.476 (5)C22—O91.206 (4)
C5—H5A0.9700C22—N61.333 (3)
C5—H5B0.9700C22—N51.431 (4)
C6—H6A0.9600C23—N61.450 (4)
C6—H6B0.9600C23—C251.516 (4)
C6—H6C0.9600C23—C241.520 (4)
C7—O31.206 (4)C23—H230.9800
C7—N31.332 (4)C24—O101.2537 (17)
C7—N21.427 (4)C24—O111.2538 (17)
C8—O41.2538 (17)C25—C261.378 (4)
C8—C91.523 (4)C25—C301.384 (4)
C9—N31.442 (4)C26—C271.383 (4)
C9—C101.513 (4)C26—H260.9300
C9—H90.9800C27—C281.378 (5)
C10—C151.378 (4)C27—H270.9300
C10—C111.381 (4)C28—O121.362 (3)
C11—C121.388 (4)C28—C291.379 (4)
C11—H110.9300C29—C301.381 (4)
C12—C131.379 (5)C29—H290.9300
C12—H120.9300C30—H300.9300
C13—O61.367 (3)N3—H30.8600
C13—C141.376 (4)N6—H6D0.8600
C14—C151.383 (4)O4—H4O0.86 (3)
C14—H140.9300O6—H60.8200
C15—H150.9300O10—H10O0.86 (3)
C16—C171.501 (6)O11—H11O0.86 (3)
C16—H16A0.9600O12—H12A0.8200
C16—H16B0.9600
C8—O5—O1079.07 (15)H17A—C17—H17B108.0
C8—O5—H5O117 (7)O7—C18—N4123.9 (3)
O10—O5—H5O43 (7)O7—C18—C19118.0 (3)
O1—C1—N1123.4 (3)N4—C18—C19117.9 (3)
O1—C1—C2118.3 (3)O8—C19—N5124.8 (3)
N1—C1—C2118.2 (3)O8—C19—C18117.9 (3)
O2—C2—N2125.1 (3)N5—C19—C18117.3 (2)
O2—C2—C1117.8 (3)N5—C20—C21110.1 (3)
N2—C2—C1117.1 (3)N5—C20—H20A109.6
N2—C3—C4110.2 (3)C21—C20—H20A109.6
N2—C3—H3A109.6N5—C20—H20B109.6
C4—C3—H3A109.6C21—C20—H20B109.6
N2—C3—H3B109.6H20A—C20—H20B108.1
C4—C3—H3B109.6N4—C21—C20110.4 (3)
H3A—C3—H3B108.1N4—C21—H21A109.6
N1—C4—C3110.2 (3)C20—C21—H21A109.6
N1—C4—H4A109.6N4—C21—H21B109.6
C3—C4—H4A109.6C20—C21—H21B109.6
N1—C4—H4B109.6H21A—C21—H21B108.1
C3—C4—H4B109.6O9—C22—N6124.3 (3)
H4A—C4—H4B108.1O9—C22—N5119.6 (3)
N1—C5—C6111.4 (3)N6—C22—N5116.1 (3)
N1—C5—H5A109.3N6—C23—C25111.0 (2)
C6—C5—H5A109.3N6—C23—C24111.6 (2)
N1—C5—H5B109.3C25—C23—C24108.3 (2)
C6—C5—H5B109.3N6—C23—H23108.7
H5A—C5—H5B108.0C25—C23—H23108.7
C5—C6—H6A109.5C24—C23—H23108.7
C5—C6—H6B109.5O10—C24—O11124.5 (3)
H6A—C6—H6B109.5O10—C24—C23117.2 (2)
C5—C6—H6C109.5O11—C24—C23118.2 (2)
H6A—C6—H6C109.5C26—C25—C30118.2 (3)
H6B—C6—H6C109.5C26—C25—C23120.7 (3)
O3—C7—N3123.5 (3)C30—C25—C23121.1 (3)
O3—C7—N2120.3 (3)C25—C26—C27121.3 (3)
N3—C7—N2116.2 (3)C25—C26—H26119.3
O5—C8—O4124.3 (3)C27—C26—H26119.3
O5—C8—C9118.9 (2)C28—C27—C26119.8 (3)
O4—C8—C9116.8 (2)C28—C27—H27120.1
N3—C9—C10109.4 (2)C26—C27—H27120.1
N3—C9—C8111.4 (2)O12—C28—C27122.7 (3)
C10—C9—C8109.4 (2)O12—C28—C29117.8 (3)
N3—C9—H9108.9C27—C28—C29119.5 (3)
C10—C9—H9108.9C28—C29—C30120.1 (3)
C8—C9—H9108.9C28—C29—H29119.9
C15—C10—C11118.2 (3)C30—C29—H29119.9
C15—C10—C9121.3 (3)C29—C30—C25121.0 (3)
C11—C10—C9120.4 (3)C29—C30—H30119.5
C10—C11—C12121.1 (3)C25—C30—H30119.5
C10—C11—H11119.4C1—N1—C4121.1 (3)
C12—C11—H11119.4C1—N1—C5119.7 (3)
C13—C12—C11119.5 (3)C4—N1—C5118.1 (2)
C13—C12—H12120.3C2—N2—C7125.5 (2)
C11—C12—H12120.3C2—N2—C3118.4 (2)
O6—C13—C14117.3 (3)C7—N2—C3116.1 (3)
O6—C13—C12122.5 (3)C7—N3—C9119.4 (3)
C14—C13—C12120.2 (3)C7—N3—H3120.3
C13—C14—C15119.5 (3)C9—N3—H3120.3
C13—C14—H14120.3C18—N4—C21121.4 (3)
C15—C14—H14120.3C18—N4—C17119.1 (3)
C10—C15—C14121.5 (3)C21—N4—C17118.4 (2)
C10—C15—H15119.3C19—N5—C22125.4 (2)
C14—C15—H15119.3C19—N5—C20117.5 (2)
C17—C16—H16A109.5C22—N5—C20117.0 (2)
C17—C16—H16B109.5C22—N6—C23119.3 (3)
H16A—C16—H16B109.5C22—N6—H6D120.4
C17—C16—H16C109.5C23—N6—H6D120.4
H16A—C16—H16C109.5C8—O4—H4O133 (6)
H16B—C16—H16C109.5C13—O6—H6109.5
N4—C17—C16111.3 (3)C24—O10—O577.75 (16)
N4—C17—H17A109.4C24—O10—H10O116 (6)
C16—C17—H17A109.4O5—O10—H10O44 (6)
N4—C17—H17B109.4C24—O11—H11O122 (6)
C16—C17—H17B109.4C28—O12—H12A109.5
O1—C1—C2—O2−15.5 (4)O1—C1—N1—C4178.2 (3)
N1—C1—C2—O2161.3 (3)C2—C1—N1—C41.6 (4)
O1—C1—C2—N2166.5 (3)O1—C1—N1—C510.9 (5)
N1—C1—C2—N2−16.8 (4)C2—C1—N1—C5−165.7 (3)
N2—C3—C4—N1−56.5 (4)C3—C4—N1—C135.1 (4)
O10—O5—C8—O4−8.8 (3)C3—C4—N1—C5−157.4 (3)
O10—O5—C8—C9174.5 (3)C6—C5—N1—C190.2 (4)
O5—C8—C9—N3−39.2 (4)C6—C5—N1—C4−77.4 (4)
O4—C8—C9—N3143.9 (3)O2—C2—N2—C7−7.5 (5)
O5—C8—C9—C1081.9 (3)C1—C2—N2—C7170.4 (3)
O4—C8—C9—C10−95.0 (3)O2—C2—N2—C3174.5 (3)
N3—C9—C10—C1559.9 (3)C1—C2—N2—C3−7.6 (4)
C8—C9—C10—C15−62.4 (3)O3—C7—N2—C2176.3 (3)
N3—C9—C10—C11−117.6 (3)N3—C7—N2—C2−3.0 (4)
C8—C9—C10—C11120.1 (3)O3—C7—N2—C3−5.7 (5)
C15—C10—C11—C120.8 (4)N3—C7—N2—C3175.0 (3)
C9—C10—C11—C12178.4 (3)C4—C3—N2—C244.0 (4)
C10—C11—C12—C13−0.3 (4)C4—C3—N2—C7−134.1 (3)
C11—C12—C13—O6180.0 (3)O3—C7—N3—C98.6 (5)
C11—C12—C13—C14−0.1 (4)N2—C7—N3—C9−172.2 (3)
O6—C13—C14—C15179.9 (3)C10—C9—N3—C7178.9 (3)
C12—C13—C14—C150.0 (5)C8—C9—N3—C7−60.1 (3)
C11—C10—C15—C14−1.0 (4)O7—C18—N4—C21179.8 (3)
C9—C10—C15—C14−178.5 (3)C19—C18—N4—C215.3 (4)
C13—C14—C15—C100.6 (5)O7—C18—N4—C1711.8 (5)
O7—C18—C19—O8−15.6 (4)C19—C18—N4—C17−162.6 (3)
N4—C18—C19—O8159.2 (3)C20—C21—N4—C1832.0 (4)
O7—C18—C19—N5166.6 (3)C20—C21—N4—C17−159.9 (3)
N4—C18—C19—N5−18.6 (4)C16—C17—N4—C1878.3 (4)
N5—C20—C21—N4−56.3 (4)C16—C17—N4—C21−90.0 (4)
N6—C23—C24—O10152.5 (3)O8—C19—N5—C22−2.6 (5)
C25—C23—C24—O10−85.1 (3)C18—C19—N5—C22175.0 (3)
N6—C23—C24—O11−30.5 (4)O8—C19—N5—C20174.1 (3)
C25—C23—C24—O1191.8 (3)C18—C19—N5—C20−8.4 (4)
N6—C23—C25—C26−120.9 (3)O9—C22—N5—C19172.3 (3)
C24—C23—C25—C26116.4 (3)N6—C22—N5—C19−9.2 (4)
N6—C23—C25—C3059.8 (3)O9—C22—N5—C20−4.4 (4)
C24—C23—C25—C30−62.9 (3)N6—C22—N5—C20174.2 (3)
C30—C25—C26—C270.7 (4)C21—C20—N5—C1945.4 (4)
C23—C25—C26—C27−178.5 (3)C21—C20—N5—C22−137.7 (3)
C25—C26—C27—C28−0.3 (5)O9—C22—N6—C23−0.4 (5)
C26—C27—C28—O12178.8 (3)N5—C22—N6—C23−178.9 (2)
C26—C27—C28—C29−0.4 (5)C25—C23—N6—C22170.7 (2)
O12—C28—C29—C30−178.6 (3)C24—C23—N6—C22−68.5 (3)
C27—C28—C29—C300.6 (5)O11—C24—O10—O5−2.3 (3)
C28—C29—C30—C25−0.1 (5)C23—C24—O10—O5174.5 (3)
C26—C25—C30—C29−0.5 (5)C8—O5—O10—C24162.7 (3)
C23—C25—C30—C29178.7 (3)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
O11—H11O···O50.86 (3)1.80 (4)2.617 (3)159 (9)
O10—H10O···O40.86 (3)1.82 (3)2.678 (3)171 (9)
O5—H5O···O110.86 (3)1.76 (3)2.617 (3)171 (8)
O4—H4O···O100.86 (3)1.88 (5)2.678 (3)154 (9)
N6—H6D···O80.861.982.637 (3)132
N3—H3···O20.861.972.636 (3)133
O6—H6···O1i0.821.872.682 (3)174
C12—H12···O2i0.932.523.438 (4)169
O12—H12A···O7ii0.821.882.692 (3)172
C27—H27···O8ii0.932.503.378 (4)158

Symmetry codes: (i) x+1/2, −y+1/2, −z+1; (ii) x+1/2, −y+5/2, −z+1.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: LX2155).

References

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