organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 69| Part 2| February 2013| Pages o293-o294

Ethyl 4-hy­dr­oxy-1-methyl-5-oxo-2-phenyl­pyrrolidine-3-carboxyl­ate 1.25-hydrate

aOrganic Synthesis Labratory, Institute of Science, Universiti Tecknologi MARA, 40450 Shah Alam, Selangor, Malaysia, and bDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
*Correspondence e-mail: hamid.khaledi@gmail.com

(Received 14 January 2013; accepted 19 January 2013; online 26 January 2013)

The asymmetric unit of the title compound, C14H17NO4·1.25H2O, consists of four substituted pyrrolidone mol­ecules (two pairs of enanti­omers) and five water mol­ecules. The five-membered rings each have an envelope conformation, with the C atom bonded to the ester group as the flap. The mean planes of the five-membered rings of the four pyrrolidone mol­ecules make dihedral angles of 60.87 (5), 64.45 (5), 62.03 (5) and 65.79 (5)° with respect to the phenyl rings. In the crystal, the pyrrolidone and water mol­ecules are connected through O—H⋯O hydrogen bonds, forming a layer parallel to the ab plane. The two-dimensional network is further stabilized by inter­molecular C—H⋯O hydrogen bonds.

Related literature

For the structures of similar compounds, see: Ma & Jiang (1998[Ma, D. & Jiang, J. (1998). Tetrahedron Asymmetry, 9, 575-579.]); Chu et al. (2011[Chu, A. M., Fettinger, J. C. & David, S. S. (2011). Bioorg. Med. Chem. Lett. 21, 4969-4972.]); Gainsford & Mason (2010[Gainsford, G. J. & Mason, J. M. (2010). Acta Cryst. E66, o957.]). For the synthesis of the precursor substituted 2,5-dihydro­pyrrole-2-one, see: Mohammat et al. (2009[Mohammat, M. F., Shaameri, Z. & Hamzah, A. S. (2009). Molecules, 14, 250-256.]).

[Scheme 1]

Experimental

Crystal data
  • C14H17NO4·1.25H2O

  • Mr = 285.81

  • Triclinic, [P \overline 1]

  • a = 10.3669 (2) Å

  • b = 15.7466 (3) Å

  • c = 18.4539 (3) Å

  • α = 77.373 (1)°

  • β = 80.425 (1)°

  • γ = 87.058 (1)°

  • V = 2898.31 (9) Å3

  • Z = 8

  • Mo Kα radiation

  • μ = 0.10 mm−1

  • T = 100 K

  • 0.21 × 0.15 × 0.09 mm

Data collection
  • Bruker APEXII CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996[Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.]) Tmin = 0.979, Tmax = 0.991

  • 22505 measured reflections

  • 11260 independent reflections

  • 9637 reflections with I > 2σ(I)

  • Rint = 0.018

Refinement
  • R[F2 > 2σ(F2)] = 0.039

  • wR(F2) = 0.104

  • S = 1.02

  • 11260 reflections

  • 780 parameters

  • 20 restraints

  • H atoms treated by a mixture of independent and constrained refinement

  • Δρmax = 0.75 e Å−3

  • Δρmin = −0.28 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
O2A—H2A⋯O5 0.81 (2) 1.86 (2) 2.6569 (16) 166 (2)
O2B—H2B⋯O1Bi 0.84 (1) 1.89 (2) 2.7111 (14) 165 (2)
O2C—H2C⋯O1Cii 0.85 (1) 1.89 (2) 2.7089 (14) 162 (2)
O2D—H2D⋯O8iii 0.82 (2) 1.92 (2) 2.7134 (17) 164 (2)
O5—H5E⋯O1Cii 0.86 (1) 1.94 (2) 2.7857 (15) 168 (2)
O5—H5F⋯O2Diii 0.86 (1) 1.79 (1) 2.6490 (17) 178 (2)
O6—H6F⋯O2Civ 0.90 (1) 1.99 (1) 2.8837 (16) 177 (2)
O6—H6E⋯O1Diii 0.88 (1) 1.96 (2) 2.8218 (15) 167 (2)
O7—H7F⋯O1A 0.87 (1) 1.97 (2) 2.8399 (16) 176 (2)
O7—H7E⋯O2Bv 0.89 (1) 2.01 (1) 2.8987 (16) 175 (2)
O8—H8E⋯O7 0.95 (2) 1.87 (2) 2.7637 (18) 156 (2)
O8—H8F⋯O9 0.91 (1) 1.93 (2) 2.8193 (18) 168 (2)
O9—H9F⋯O2A 0.84 (2) 1.98 (2) 2.8199 (17) 176 (2)
O9—H9E⋯O6 0.90 (1) 1.93 (2) 2.7724 (18) 155 (2)
C3B—H3B⋯O1Avi 1.00 2.45 3.2581 (17) 138
C3C—H3C⋯O1D 1.00 2.31 3.1537 (17) 142
C3D—H3D⋯O1Diii 1.00 2.56 3.4252 (18) 145
C5A—H5A⋯O7v 1.00 2.34 3.2374 (18) 148
C5B—H5B⋯O9vi 1.00 2.40 3.2568 (19) 143
C5C—H5C⋯O8iii 1.00 2.49 3.2395 (19) 131
C5D—H5D⋯O6 1.00 2.41 3.2010 (18) 135
C7A—H7A⋯O3B 0.95 2.38 3.2943 (17) 162
C7B—H7B⋯O3Avi 0.95 2.46 3.3253 (18) 151
C7C—H7C⋯O3D 0.95 2.39 3.2704 (18) 155
C11A—H11A⋯O4Biv 0.95 2.54 3.3027 (17) 138
Symmetry codes: (i) -x, -y, -z+1; (ii) -x, -y+1, -z+1; (iii) -x+1, -y+1, -z+1; (iv) x+1, y, z; (v) -x+1, -y, -z+1; (vi) x-1, y, z.

Data collection: APEX2 (Bruker, 2007[Bruker (2007). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2007[Bruker (2007). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: X-SEED (Barbour, 2001[Barbour, L. J. (2001). J. Supramol. Chem. 1, 189-191.]); software used to prepare material for publication: SHELXL97 and publCIF (Westrip, 2010[Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.]).

Supporting information


Comment top

Polyfunctionalized pyrrolidones have received significant attention in the past decades due to their role as intermediates for synthesizing more complex biologically important molecules (Ma & Jiang, 1998). The present pyrrolidone molecule was prepared through catalytic hydrogenation of the previously reported substituted 2,5-dihydropyrrole-2-one (Mohammat et al., 2009). The asymmetric unit of the crystal (Fig. 1) contains four geometrically slightly different pyrrolidone molecules: A (Fig. 2), B, C & D. The weighted r.m.s. fit for the superposition of the non-H atoms is 0.097 Å (in A & B with inversion), 0.082 Å (in A & C), 0.107 Å (in A & D with inversion), 0.141 Å (in B & C with inversion), 0.034 Å (in B & D) and 0.138 Å (in C & D with inversion). The planes of the phenyl and pyrrolidine rings in the four molecules make dihedral angles of 60.87 (5), 64.45 (5), 62.03 (5) and 65.79 (5)°. The bond lengths and angles in the four molecules are comparable to those in similar structures (Chu et al., 2011; Gainsford & Mason, 2010). There are five crystallographically independent water molecules in the crystal structure, connecting the pyrrolidone molecules into a layer parallel to the ab plane via O—H···O hydrogen bonds (Table 1). The supramolecular structure is further consolidated by intermolecular C—H···O interactions (Table 1).

Related literature top

For the structures of similar compounds, see: Ma & Jiang (1998); Chu et al. (2011); Gainsford & Mason (2010). For the synthesis of the precursor substituted 2,5-dihydropyrrole-2-one, see: Mohammat et al. (2009).

Experimental top

The synthetic approach to the title compound began with the preparation of ethyl 4-hydroxy-1-methyl-5-oxo-2-phenyl-2,5-dihydropyrrole-3-carboxylate as reported by (Mohammat et al., 2009). This compound was catalytically hydrogenated by addition of Pd—C (10% wt) (0.91 g, 8.60 mmol) to its stirring solution (1.69 g, 6.47 mmol) in ethanol (110 ml) under hydrogen atmosphere for 24 h. The mixture was then filtered through celite. After removal of the solvent, the crude product was purified by column chromatography using silica gel (eluent: EtOAc) to give the diastereomeric product as a white solid (1.20 g, 71%). Slow evaporation of an ethyl acetate solution of the product at room temperature gave colorless crystals of the title compound.

Refinement top

The C-bound hydrogen atoms were located in calculated positions and refined in a riding mode with C—H distances of 0.95–1.00 Å. The O-bound H atoms were found in a difference Fourier map and refined with distance restraints of O—H = 0.88 (2) and H···H = 1.41 (1) Å (for the water molecules) and O—H = 0.84 (2) Å (for the hydroxyl groups). For all hydrogen atoms, Uiso were set to 1.2–1.5Ueq(carrier atom). The most disagreeable reflections with delta(F2)/e.s.d. >10 were omitted (4 reflections).

Computing details top

Data collection: APEX2 (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: X-SEED (Barbour, 2001); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008) and publCIF (Westrip, 2010).

Figures top
[Figure 1] Fig. 1. The asymmetric unit of the title compound, showing thermal ellipsoids at the 30% prbability level. C-bound hydrogen atoms are omitted for clarity.
[Figure 2] Fig. 2. The molecular structure of one of the four independent organic molecules in the asymmetric unit (molecule A), showing atom-labelling scheme and thermal ellipsoids at 50% probability levels. The other three organic molecules are labelled in a similar manner.
Ethyl 4-hydroxy-1-methyl-5-oxo-2-phenylpyrrolidine-3-carboxylate 1.25-hydrate top
Crystal data top
C14H17NO4·1.25H2OZ = 8
Mr = 285.81F(000) = 1220
Triclinic, P1Dx = 1.310 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 10.3669 (2) ÅCell parameters from 9907 reflections
b = 15.7466 (3) Åθ = 2.4–29.7°
c = 18.4539 (3) ŵ = 0.10 mm1
α = 77.373 (1)°T = 100 K
β = 80.425 (1)°Block, colorless
γ = 87.058 (1)°0.21 × 0.15 × 0.09 mm
V = 2898.31 (9) Å3
Data collection top
Bruker APEXII CCD
diffractometer
11260 independent reflections
Radiation source: fine-focus sealed tube9637 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.018
ϕ and ω scansθmax = 26.0°, θmin = 1.9°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 1212
Tmin = 0.979, Tmax = 0.991k = 1919
22505 measured reflectionsl = 2222
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)] = 0.039Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.104H atoms treated by a mixture of independent and constrained refinement
S = 1.02 w = 1/[σ2(Fo2) + (0.0505P)2 + 1.2863P]
where P = (Fo2 + 2Fc2)/3
11260 reflections(Δ/σ)max = 0.001
780 parametersΔρmax = 0.75 e Å3
20 restraintsΔρmin = 0.28 e Å3
Crystal data top
C14H17NO4·1.25H2Oγ = 87.058 (1)°
Mr = 285.81V = 2898.31 (9) Å3
Triclinic, P1Z = 8
a = 10.3669 (2) ÅMo Kα radiation
b = 15.7466 (3) ŵ = 0.10 mm1
c = 18.4539 (3) ÅT = 100 K
α = 77.373 (1)°0.21 × 0.15 × 0.09 mm
β = 80.425 (1)°
Data collection top
Bruker APEXII CCD
diffractometer
11260 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
9637 reflections with I > 2σ(I)
Tmin = 0.979, Tmax = 0.991Rint = 0.018
22505 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.03920 restraints
wR(F2) = 0.104H atoms treated by a mixture of independent and constrained refinement
S = 1.02Δρmax = 0.75 e Å3
11260 reflectionsΔρmin = 0.28 e Å3
780 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
O1A0.64901 (10)0.04071 (7)0.45502 (6)0.0238 (2)
O2A0.49840 (11)0.20181 (7)0.41628 (6)0.0242 (2)
H2A0.4372 (17)0.2196 (13)0.4425 (10)0.036*
O3A0.64351 (10)0.21091 (7)0.26500 (6)0.0220 (2)
O4A0.45909 (10)0.25338 (6)0.21664 (6)0.0202 (2)
N1A0.58255 (11)0.01013 (8)0.35122 (7)0.0188 (3)
C1A0.64186 (17)0.07648 (10)0.35670 (10)0.0303 (4)
H1AA0.68880.09000.39990.045*
H1AB0.70330.07830.31050.045*
H1AC0.57340.11940.36340.045*
C2A0.57953 (13)0.05509 (9)0.40585 (8)0.0180 (3)
C3A0.47030 (13)0.12313 (9)0.39841 (8)0.0174 (3)
H3A0.39040.09850.43340.021*
C4A0.44481 (13)0.13153 (9)0.31760 (8)0.0157 (3)
H4A0.35010.14400.31440.019*
C5A0.48550 (13)0.04019 (9)0.30133 (8)0.0167 (3)
H5A0.40800.00130.31830.020*
C6A0.53553 (14)0.04127 (9)0.21912 (8)0.0171 (3)
C7A0.44476 (14)0.03707 (9)0.17244 (8)0.0200 (3)
H7A0.35460.03070.19290.024*
C8A0.48543 (15)0.04213 (10)0.09585 (9)0.0228 (3)
H8A0.42270.04000.06420.027*
C9A0.61664 (15)0.05028 (10)0.06559 (9)0.0230 (3)
H9A0.64420.05360.01330.028*
C10A0.70755 (14)0.05353 (10)0.11199 (9)0.0228 (3)
H10A0.79790.05820.09160.027*
C11A0.66731 (14)0.04995 (9)0.18827 (8)0.0205 (3)
H11A0.73010.05340.21950.025*
C12A0.52894 (13)0.20185 (9)0.26489 (8)0.0164 (3)
C13A0.53044 (16)0.32175 (10)0.16058 (9)0.0250 (3)
H13C0.59600.34610.18340.030*
H13D0.46890.36930.14370.030*
C14A0.59860 (16)0.28733 (10)0.09366 (9)0.0270 (3)
H14D0.66510.24390.10960.040*
H14E0.64050.33540.05530.040*
H14F0.53440.26030.07270.040*
O1B0.13260 (10)0.11970 (7)0.45539 (6)0.0224 (2)
O2B0.00506 (10)0.01771 (7)0.41779 (6)0.0200 (2)
H2B0.0561 (16)0.0427 (12)0.4561 (9)0.030*
O3B0.14893 (9)0.03902 (7)0.27056 (6)0.0219 (2)
O4B0.02826 (10)0.01861 (7)0.22088 (6)0.0218 (2)
N1B0.07124 (11)0.20140 (8)0.34704 (7)0.0178 (2)
C1B0.12896 (16)0.28289 (10)0.34959 (9)0.0259 (3)
H1BA0.05960.32670.35540.039*
H1BB0.18940.30320.30280.039*
H1BC0.17670.27360.39230.039*
C2B0.06659 (13)0.13149 (9)0.40419 (8)0.0172 (3)
C3B0.03891 (13)0.07115 (9)0.39767 (8)0.0167 (3)
H3B0.12140.08280.43090.020*
C4B0.05891 (13)0.10050 (9)0.31525 (8)0.0163 (3)
H4B0.15170.09270.30980.020*
C5B0.02377 (13)0.19877 (9)0.29672 (8)0.0167 (3)
H5B0.10370.23270.31260.020*
C6B0.02584 (14)0.23547 (9)0.21441 (8)0.0169 (3)
C7B0.06444 (14)0.27310 (10)0.16819 (8)0.0208 (3)
H7B0.15400.27750.18910.025*
C8B0.02433 (15)0.30423 (10)0.09168 (9)0.0244 (3)
H8B0.08660.32940.06050.029*
C9B0.10633 (16)0.29868 (10)0.06066 (9)0.0246 (3)
H9B0.13360.31990.00830.029*
C10B0.19687 (15)0.26215 (10)0.10625 (9)0.0227 (3)
H10B0.28660.25870.08510.027*
C11B0.15721 (14)0.23044 (9)0.18279 (8)0.0200 (3)
H11B0.21990.20520.21370.024*
C12B0.03408 (13)0.04982 (9)0.26770 (8)0.0165 (3)
C13B0.05179 (17)0.02891 (10)0.16992 (9)0.0288 (4)
H13E0.00250.07230.15790.035*
H13F0.12310.06050.19480.035*
C14B0.10956 (16)0.03211 (11)0.09840 (9)0.0296 (4)
H14G0.03930.06630.07560.044*
H14H0.15680.00160.06330.044*
H14I0.17010.07130.10980.044*
O1C0.10524 (10)0.63323 (7)0.46461 (6)0.0221 (2)
O2C0.03047 (10)0.48233 (6)0.41740 (6)0.0204 (2)
H2C0.0678 (17)0.4530 (11)0.4525 (9)0.031*
O3C0.04204 (10)0.54456 (7)0.26963 (6)0.0211 (2)
O4C0.16347 (10)0.51174 (7)0.22014 (6)0.0211 (2)
N1C0.00350 (11)0.70649 (8)0.35085 (7)0.0177 (2)
C1C0.04334 (16)0.79432 (10)0.35577 (9)0.0259 (3)
H1CA0.09860.79280.40460.039*
H1CB0.09440.81730.31540.039*
H1CC0.03150.83190.35060.039*
C2C0.01997 (13)0.63793 (9)0.40823 (8)0.0173 (3)
C3C0.08167 (13)0.56697 (9)0.39700 (8)0.0166 (3)
H3C0.15090.56990.42820.020*
C4C0.14199 (13)0.59354 (9)0.31376 (8)0.0160 (3)
H4C0.23790.57980.30680.019*
C5C0.11761 (13)0.69378 (9)0.29505 (8)0.0162 (3)
H5C0.19420.72290.30520.019*
C6C0.09907 (13)0.73012 (9)0.21423 (8)0.0168 (3)
C7C0.21080 (14)0.75141 (9)0.16050 (8)0.0199 (3)
H7C0.29460.74600.17570.024*
C8C0.20017 (15)0.78040 (10)0.08495 (8)0.0237 (3)
H8C0.27670.79400.04860.028*
C9C0.07817 (16)0.78955 (10)0.06253 (9)0.0254 (3)
H9C0.07080.80990.01100.030*
C10C0.03285 (15)0.76886 (10)0.11569 (9)0.0243 (3)
H10C0.11660.77520.10050.029*
C11C0.02266 (14)0.73883 (9)0.19119 (8)0.0205 (3)
H11C0.09930.72420.22720.025*
C12C0.07442 (13)0.54789 (9)0.26684 (8)0.0165 (3)
C13C0.11189 (16)0.47051 (10)0.16792 (9)0.0262 (3)
H13G0.02910.44110.19310.031*
H13H0.17510.42590.15270.031*
C14C0.08725 (16)0.53705 (11)0.09926 (9)0.0269 (3)
H14J0.02190.57980.11420.040*
H14K0.05480.50800.06410.040*
H14L0.16900.56660.07480.040*
O1D0.35787 (10)0.51833 (7)0.44621 (6)0.0237 (2)
O2D0.50430 (11)0.67992 (7)0.41422 (7)0.0290 (3)
H2D0.4278 (16)0.6933 (14)0.4118 (12)0.043*
O3D0.44459 (10)0.69891 (7)0.26203 (6)0.0256 (2)
O4D0.64862 (10)0.74790 (7)0.21751 (6)0.0235 (2)
N1D0.48531 (11)0.49696 (8)0.33763 (7)0.0177 (2)
C1D0.43039 (16)0.41419 (10)0.33667 (9)0.0262 (3)
H1DA0.36350.39720.38120.039*
H1DB0.49990.36960.33710.039*
H1DC0.39070.42000.29120.039*
C2D0.45232 (14)0.53649 (9)0.39610 (8)0.0185 (3)
C3D0.55444 (14)0.60389 (9)0.39124 (8)0.0194 (3)
H3D0.61830.57680.42500.023*
C4D0.62603 (13)0.61722 (9)0.30972 (8)0.0174 (3)
H4D0.72090.62880.30680.021*
C5D0.60730 (13)0.52840 (9)0.28869 (8)0.0169 (3)
H5D0.68010.48800.30420.020*
C6D0.60521 (14)0.53365 (9)0.20598 (8)0.0173 (3)
C7D0.72226 (14)0.51983 (10)0.16043 (8)0.0211 (3)
H7D0.79990.50580.18190.025*
C8D0.72600 (16)0.52651 (11)0.08379 (9)0.0261 (3)
H8D0.80620.51690.05310.031*
C9D0.61378 (16)0.54704 (10)0.05188 (9)0.0265 (3)
H9D0.61680.55210.00060.032*
C10D0.49682 (16)0.56017 (10)0.09706 (9)0.0247 (3)
H10D0.41930.57390.07540.030*
C11D0.49217 (14)0.55343 (9)0.17381 (8)0.0205 (3)
H11D0.41160.56230.20440.025*
C12D0.56095 (14)0.69130 (9)0.26130 (8)0.0187 (3)
C13D0.59552 (17)0.82097 (10)0.16744 (10)0.0300 (4)
H13A0.65480.87110.15670.036*
H13B0.50940.83860.19240.036*
C14D0.58004 (17)0.79696 (11)0.09471 (9)0.0313 (4)
H14A0.66520.77920.07010.047*
H14B0.54580.84730.06150.047*
H14C0.51900.74870.10520.047*
O50.32498 (11)0.25906 (7)0.51861 (8)0.0321 (3)
H5E0.2567 (15)0.2925 (13)0.5169 (12)0.048*
H5F0.3790 (16)0.2792 (13)0.5414 (12)0.048*
O60.76502 (11)0.43383 (8)0.41992 (6)0.0287 (3)
H6E0.7240 (16)0.4400 (13)0.4641 (9)0.043*
H6F0.8469 (14)0.4507 (13)0.4182 (11)0.043*
O70.73659 (11)0.07895 (8)0.58207 (7)0.0302 (3)
H7E0.8181 (15)0.0577 (13)0.5805 (11)0.045*
H7F0.7098 (17)0.0702 (14)0.5420 (10)0.045*
O80.74438 (13)0.25573 (9)0.57526 (7)0.0376 (3)
H8E0.732 (2)0.1948 (10)0.5919 (10)0.056*
H8F0.758 (2)0.2590 (13)0.5249 (8)0.056*
O90.74986 (13)0.25813 (9)0.42157 (7)0.0378 (3)
H9E0.747 (2)0.3165 (10)0.4075 (12)0.057*
H9F0.6757 (17)0.2394 (12)0.4216 (13)0.057*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O1A0.0207 (5)0.0312 (6)0.0185 (5)0.0011 (4)0.0069 (4)0.0002 (4)
O2A0.0252 (6)0.0248 (6)0.0255 (6)0.0023 (4)0.0021 (5)0.0139 (5)
O3A0.0175 (5)0.0255 (6)0.0218 (5)0.0040 (4)0.0019 (4)0.0027 (4)
O4A0.0223 (5)0.0180 (5)0.0183 (5)0.0004 (4)0.0038 (4)0.0008 (4)
N1A0.0196 (6)0.0174 (6)0.0189 (6)0.0035 (5)0.0047 (5)0.0024 (5)
C1A0.0361 (9)0.0210 (8)0.0326 (9)0.0100 (7)0.0086 (7)0.0033 (7)
C2A0.0153 (7)0.0207 (7)0.0153 (7)0.0033 (5)0.0001 (5)0.0007 (6)
C3A0.0161 (7)0.0204 (7)0.0154 (7)0.0009 (5)0.0008 (5)0.0043 (6)
C4A0.0135 (6)0.0174 (7)0.0157 (7)0.0008 (5)0.0019 (5)0.0030 (5)
C5A0.0155 (6)0.0162 (7)0.0176 (7)0.0004 (5)0.0022 (5)0.0025 (6)
C6A0.0189 (7)0.0145 (7)0.0179 (7)0.0003 (5)0.0018 (6)0.0042 (5)
C7A0.0176 (7)0.0208 (7)0.0217 (8)0.0017 (5)0.0011 (6)0.0062 (6)
C8A0.0245 (8)0.0248 (8)0.0213 (8)0.0006 (6)0.0062 (6)0.0079 (6)
C9A0.0298 (8)0.0220 (7)0.0170 (7)0.0023 (6)0.0007 (6)0.0066 (6)
C10A0.0182 (7)0.0253 (8)0.0246 (8)0.0032 (6)0.0029 (6)0.0090 (6)
C11A0.0183 (7)0.0224 (7)0.0225 (8)0.0007 (6)0.0035 (6)0.0078 (6)
C12A0.0189 (7)0.0153 (7)0.0158 (7)0.0012 (5)0.0023 (5)0.0059 (5)
C13A0.0329 (8)0.0168 (7)0.0218 (8)0.0012 (6)0.0026 (6)0.0021 (6)
C14A0.0315 (8)0.0271 (8)0.0201 (8)0.0036 (7)0.0021 (6)0.0011 (6)
O1B0.0234 (5)0.0263 (6)0.0171 (5)0.0056 (4)0.0067 (4)0.0002 (4)
O2B0.0225 (5)0.0178 (5)0.0169 (5)0.0022 (4)0.0003 (4)0.0003 (4)
O3B0.0165 (5)0.0271 (6)0.0205 (5)0.0028 (4)0.0012 (4)0.0037 (4)
O4B0.0220 (5)0.0245 (5)0.0213 (5)0.0019 (4)0.0022 (4)0.0108 (4)
N1B0.0197 (6)0.0180 (6)0.0159 (6)0.0034 (5)0.0039 (5)0.0029 (5)
C1B0.0362 (9)0.0202 (8)0.0227 (8)0.0080 (6)0.0074 (7)0.0036 (6)
C2B0.0164 (7)0.0203 (7)0.0138 (7)0.0007 (5)0.0005 (5)0.0033 (6)
C3B0.0158 (7)0.0183 (7)0.0154 (7)0.0008 (5)0.0008 (5)0.0032 (6)
C4B0.0139 (6)0.0194 (7)0.0155 (7)0.0013 (5)0.0014 (5)0.0038 (6)
C5B0.0160 (7)0.0180 (7)0.0162 (7)0.0005 (5)0.0026 (5)0.0038 (6)
C6B0.0199 (7)0.0149 (7)0.0163 (7)0.0024 (5)0.0027 (5)0.0038 (5)
C7B0.0199 (7)0.0218 (7)0.0211 (7)0.0024 (6)0.0044 (6)0.0039 (6)
C8B0.0285 (8)0.0243 (8)0.0210 (8)0.0039 (6)0.0103 (6)0.0008 (6)
C9B0.0330 (8)0.0244 (8)0.0153 (7)0.0086 (6)0.0008 (6)0.0025 (6)
C10B0.0212 (7)0.0239 (8)0.0222 (8)0.0047 (6)0.0018 (6)0.0059 (6)
C11B0.0202 (7)0.0199 (7)0.0199 (7)0.0022 (5)0.0037 (6)0.0037 (6)
C12B0.0186 (7)0.0152 (7)0.0142 (7)0.0022 (5)0.0010 (5)0.0008 (5)
C13B0.0365 (9)0.0251 (8)0.0271 (9)0.0000 (7)0.0002 (7)0.0150 (7)
C14B0.0273 (8)0.0375 (9)0.0246 (8)0.0030 (7)0.0005 (7)0.0116 (7)
O1C0.0210 (5)0.0224 (5)0.0182 (5)0.0060 (4)0.0027 (4)0.0003 (4)
O2C0.0247 (5)0.0174 (5)0.0173 (5)0.0016 (4)0.0045 (4)0.0007 (4)
O3C0.0181 (5)0.0252 (5)0.0200 (5)0.0024 (4)0.0034 (4)0.0040 (4)
O4C0.0226 (5)0.0230 (5)0.0199 (5)0.0032 (4)0.0035 (4)0.0102 (4)
N1C0.0186 (6)0.0170 (6)0.0158 (6)0.0025 (5)0.0002 (5)0.0022 (5)
C1C0.0316 (8)0.0183 (7)0.0235 (8)0.0058 (6)0.0023 (7)0.0015 (6)
C2C0.0170 (7)0.0192 (7)0.0155 (7)0.0014 (5)0.0039 (5)0.0029 (6)
C3C0.0171 (7)0.0173 (7)0.0147 (7)0.0019 (5)0.0032 (5)0.0023 (5)
C4C0.0140 (6)0.0180 (7)0.0157 (7)0.0020 (5)0.0024 (5)0.0034 (5)
C5C0.0147 (6)0.0176 (7)0.0157 (7)0.0003 (5)0.0012 (5)0.0034 (5)
C6C0.0191 (7)0.0144 (7)0.0172 (7)0.0004 (5)0.0032 (5)0.0037 (5)
C7C0.0193 (7)0.0204 (7)0.0195 (7)0.0010 (5)0.0029 (6)0.0032 (6)
C8C0.0278 (8)0.0238 (8)0.0173 (7)0.0029 (6)0.0009 (6)0.0022 (6)
C9C0.0385 (9)0.0208 (7)0.0176 (7)0.0015 (6)0.0103 (7)0.0011 (6)
C10C0.0259 (8)0.0229 (8)0.0263 (8)0.0006 (6)0.0133 (6)0.0032 (6)
C11C0.0192 (7)0.0193 (7)0.0224 (8)0.0016 (5)0.0036 (6)0.0026 (6)
C12C0.0189 (7)0.0151 (7)0.0139 (7)0.0009 (5)0.0025 (5)0.0000 (5)
C13C0.0336 (9)0.0242 (8)0.0247 (8)0.0027 (6)0.0067 (7)0.0127 (7)
C14C0.0287 (8)0.0334 (9)0.0204 (8)0.0030 (7)0.0030 (6)0.0093 (7)
O1D0.0205 (5)0.0320 (6)0.0159 (5)0.0039 (4)0.0000 (4)0.0026 (4)
O2D0.0264 (6)0.0300 (6)0.0358 (7)0.0114 (5)0.0078 (5)0.0190 (5)
O3D0.0186 (5)0.0286 (6)0.0276 (6)0.0025 (4)0.0066 (4)0.0000 (5)
O4D0.0237 (5)0.0190 (5)0.0263 (6)0.0029 (4)0.0054 (4)0.0000 (4)
N1D0.0195 (6)0.0185 (6)0.0141 (6)0.0009 (5)0.0006 (5)0.0031 (5)
C1D0.0320 (8)0.0214 (8)0.0230 (8)0.0070 (6)0.0013 (7)0.0029 (6)
C2D0.0183 (7)0.0216 (7)0.0145 (7)0.0060 (5)0.0047 (6)0.0011 (6)
C3D0.0199 (7)0.0228 (7)0.0176 (7)0.0057 (6)0.0063 (6)0.0080 (6)
C4D0.0155 (7)0.0193 (7)0.0182 (7)0.0004 (5)0.0045 (5)0.0045 (6)
C5D0.0166 (7)0.0180 (7)0.0156 (7)0.0010 (5)0.0019 (5)0.0034 (5)
C6D0.0204 (7)0.0154 (7)0.0154 (7)0.0024 (5)0.0012 (6)0.0029 (5)
C7D0.0190 (7)0.0245 (8)0.0201 (7)0.0030 (6)0.0014 (6)0.0063 (6)
C8D0.0255 (8)0.0318 (9)0.0197 (8)0.0075 (6)0.0056 (6)0.0082 (7)
C9D0.0372 (9)0.0282 (8)0.0144 (7)0.0099 (7)0.0021 (6)0.0044 (6)
C10D0.0277 (8)0.0259 (8)0.0219 (8)0.0045 (6)0.0091 (6)0.0033 (6)
C11D0.0203 (7)0.0219 (7)0.0189 (7)0.0018 (6)0.0017 (6)0.0044 (6)
C12D0.0196 (7)0.0184 (7)0.0198 (7)0.0000 (5)0.0046 (6)0.0065 (6)
C13D0.0360 (9)0.0175 (7)0.0337 (9)0.0021 (6)0.0084 (7)0.0032 (7)
C14D0.0304 (9)0.0313 (9)0.0282 (9)0.0014 (7)0.0067 (7)0.0039 (7)
O50.0199 (6)0.0264 (6)0.0495 (8)0.0046 (5)0.0041 (5)0.0093 (5)
O60.0268 (6)0.0369 (7)0.0243 (6)0.0008 (5)0.0031 (5)0.0117 (5)
O70.0267 (6)0.0350 (7)0.0300 (6)0.0034 (5)0.0075 (5)0.0081 (5)
O80.0438 (7)0.0417 (7)0.0315 (7)0.0013 (6)0.0086 (6)0.0146 (6)
O90.0423 (7)0.0394 (7)0.0359 (7)0.0054 (6)0.0062 (6)0.0188 (6)
Geometric parameters (Å, º) top
O1A—C2A1.2266 (17)O4C—C13C1.4549 (18)
O2A—C3A1.4057 (17)N1C—C2C1.3371 (18)
O2A—H2A0.809 (15)N1C—C1C1.4589 (18)
O3A—C12A1.2039 (17)N1C—C5C1.4698 (17)
O4A—C12A1.3469 (17)C1C—H1CA0.9800
O4A—C13A1.4548 (17)C1C—H1CB0.9800
N1A—C2A1.3482 (19)C1C—H1CC0.9800
N1A—C1A1.4568 (19)C2C—C3C1.5196 (19)
N1A—C5A1.4671 (18)C3C—C4C1.5337 (19)
C1A—H1AA0.9800C3C—H3C1.0000
C1A—H1AB0.9800C4C—C12C1.5109 (19)
C1A—H1AC0.9800C4C—C5C1.5571 (19)
C2A—C3A1.5205 (19)C4C—H4C1.0000
C3A—C4A1.5338 (19)C5C—C6C1.5164 (19)
C3A—H3A1.0000C5C—H5C1.0000
C4A—C12A1.5095 (19)C6C—C11C1.388 (2)
C4A—C5A1.5561 (19)C6C—C7C1.396 (2)
C4A—H4A1.0000C7C—C8C1.390 (2)
C5A—C6A1.5163 (19)C7C—H7C0.9500
C5A—H5A1.0000C8C—C9C1.386 (2)
C6A—C7A1.390 (2)C8C—H8C0.9500
C6A—C11A1.391 (2)C9C—C10C1.384 (2)
C7A—C8A1.392 (2)C9C—H9C0.9500
C7A—H7A0.9500C10C—C11C1.390 (2)
C8A—C9A1.383 (2)C10C—H10C0.9500
C8A—H8A0.9500C11C—H11C0.9500
C9A—C10A1.384 (2)C13C—C14C1.506 (2)
C9A—H9A0.9500C13C—H13G0.9900
C10A—C11A1.390 (2)C13C—H13H0.9900
C10A—H10A0.9500C14C—H14J0.9800
C11A—H11A0.9500C14C—H14K0.9800
C13A—C14A1.510 (2)C14C—H14L0.9800
C13A—H13C0.9900O1D—C2D1.2278 (18)
C13A—H13D0.9900O2D—C3D1.4029 (17)
C14A—H14D0.9800O2D—H2D0.815 (15)
C14A—H14E0.9800O3D—C12D1.2042 (17)
C14A—H14F0.9800O4D—C12D1.3406 (18)
O1B—C2B1.2333 (17)O4D—C13D1.4561 (18)
O2B—C3B1.4087 (17)N1D—C2D1.3481 (19)
O2B—H2B0.842 (14)N1D—C1D1.4535 (19)
O3B—C12B1.2023 (17)N1D—C5D1.4659 (18)
O4B—C12B1.3454 (17)C1D—H1DA0.9800
O4B—C13B1.4551 (18)C1D—H1DB0.9800
N1B—C2B1.3443 (18)C1D—H1DC0.9800
N1B—C1B1.4566 (18)C2D—C3D1.516 (2)
N1B—C5B1.4695 (18)C3D—C4D1.538 (2)
C1B—H1BA0.9800C3D—H3D1.0000
C1B—H1BB0.9800C4D—C12D1.5094 (19)
C1B—H1BC0.9800C4D—C5D1.5603 (19)
C2B—C3B1.5210 (19)C4D—H4D1.0000
C3B—C4B1.5356 (19)C5D—C6D1.5142 (19)
C3B—H3B1.0000C5D—H5D1.0000
C4B—C12B1.5105 (19)C6D—C11D1.391 (2)
C4B—C5B1.5587 (19)C6D—C7D1.393 (2)
C4B—H4B1.0000C7D—C8D1.389 (2)
C5B—C6B1.5142 (19)C7D—H7D0.9500
C5B—H5B1.0000C8D—C9D1.382 (2)
C6B—C7B1.394 (2)C8D—H8D0.9500
C6B—C11B1.395 (2)C9D—C10D1.386 (2)
C7B—C8B1.389 (2)C9D—H9D0.9500
C7B—H7B0.9500C10D—C11D1.390 (2)
C8B—C9B1.386 (2)C10D—H10D0.9500
C8B—H8B0.9500C11D—H11D0.9500
C9B—C10B1.384 (2)C13D—C14D1.506 (2)
C9B—H9B0.9500C13D—H13A0.9900
C10B—C11B1.390 (2)C13D—H13B0.9900
C10B—H10B0.9500C14D—H14A0.9800
C11B—H11B0.9500C14D—H14B0.9800
C13B—C14B1.505 (2)C14D—H14C0.9800
C13B—H13E0.9900O5—H5E0.861 (14)
C13B—H13F0.9900O5—H5F0.864 (14)
C14B—H14G0.9800O6—H6E0.877 (14)
C14B—H14H0.9800O6—H6F0.895 (14)
C14B—H14I0.9800O7—H7E0.892 (14)
O1C—C2C1.2395 (17)O7—H7F0.871 (14)
O2C—C3C1.4096 (17)O8—H8E0.949 (15)
O2C—H2C0.847 (14)O8—H8F0.906 (14)
O3C—C12C1.2031 (17)O9—H9E0.899 (14)
O4C—C12C1.3472 (17)O9—H9F0.838 (15)
C3A—O2A—H2A112.0 (14)C2C—N1C—C5C113.34 (11)
C12A—O4A—C13A116.42 (11)C1C—N1C—C5C119.94 (11)
C2A—N1A—C1A121.99 (13)N1C—C1C—H1CA109.5
C2A—N1A—C5A113.88 (11)N1C—C1C—H1CB109.5
C1A—N1A—C5A120.92 (12)H1CA—C1C—H1CB109.5
N1A—C1A—H1AA109.5N1C—C1C—H1CC109.5
N1A—C1A—H1AB109.5H1CA—C1C—H1CC109.5
H1AA—C1A—H1AB109.5H1CB—C1C—H1CC109.5
N1A—C1A—H1AC109.5O1C—C2C—N1C126.51 (13)
H1AA—C1A—H1AC109.5O1C—C2C—C3C124.09 (12)
H1AB—C1A—H1AC109.5N1C—C2C—C3C109.26 (12)
O1A—C2A—N1A125.70 (13)O2C—C3C—C2C113.76 (11)
O1A—C2A—C3A126.07 (13)O2C—C3C—C4C113.58 (11)
N1A—C2A—C3A108.15 (12)C2C—C3C—C4C103.96 (11)
O2A—C3A—C2A113.95 (11)O2C—C3C—H3C108.4
O2A—C3A—C4A114.69 (11)C2C—C3C—H3C108.4
C2A—C3A—C4A103.82 (11)C4C—C3C—H3C108.4
O2A—C3A—H3A108.0C12C—C4C—C3C110.32 (11)
C2A—C3A—H3A108.0C12C—C4C—C5C111.80 (11)
C4A—C3A—H3A108.0C3C—C4C—C5C103.19 (11)
C12A—C4A—C3A110.07 (11)C12C—C4C—H4C110.4
C12A—C4A—C5A111.26 (11)C3C—C4C—H4C110.4
C3A—C4A—C5A103.00 (11)C5C—C4C—H4C110.4
C12A—C4A—H4A110.8N1C—C5C—C6C114.00 (11)
C3A—C4A—H4A110.8N1C—C5C—C4C103.28 (10)
C5A—C4A—H4A110.8C6C—C5C—C4C113.98 (11)
N1A—C5A—C6A114.11 (11)N1C—C5C—H5C108.4
N1A—C5A—C4A102.66 (11)C6C—C5C—H5C108.4
C6A—C5A—C4A113.89 (11)C4C—C5C—H5C108.4
N1A—C5A—H5A108.6C11C—C6C—C7C119.09 (13)
C6A—C5A—H5A108.6C11C—C6C—C5C122.96 (13)
C4A—C5A—H5A108.6C7C—C6C—C5C117.87 (12)
C7A—C6A—C11A119.07 (13)C8C—C7C—C6C120.38 (14)
C7A—C6A—C5A118.23 (12)C8C—C7C—H7C119.8
C11A—C6A—C5A122.65 (13)C6C—C7C—H7C119.8
C6A—C7A—C8A120.30 (13)C9C—C8C—C7C120.14 (14)
C6A—C7A—H7A119.9C9C—C8C—H8C119.9
C8A—C7A—H7A119.9C7C—C8C—H8C119.9
C9A—C8A—C7A120.36 (14)C10C—C9C—C8C119.63 (14)
C9A—C8A—H8A119.8C10C—C9C—H9C120.2
C7A—C8A—H8A119.8C8C—C9C—H9C120.2
C8A—C9A—C10A119.55 (14)C9C—C10C—C11C120.46 (14)
C8A—C9A—H9A120.2C9C—C10C—H10C119.8
C10A—C9A—H9A120.2C11C—C10C—H10C119.8
C9A—C10A—C11A120.35 (14)C6C—C11C—C10C120.29 (14)
C9A—C10A—H10A119.8C6C—C11C—H11C119.9
C11A—C10A—H10A119.8C10C—C11C—H11C119.9
C10A—C11A—C6A120.36 (14)O3C—C12C—O4C124.24 (13)
C10A—C11A—H11A119.8O3C—C12C—C4C125.48 (13)
C6A—C11A—H11A119.8O4C—C12C—C4C110.28 (11)
O3A—C12A—O4A123.95 (13)O4C—C13C—C14C110.57 (12)
O3A—C12A—C4A125.07 (13)O4C—C13C—H13G109.5
O4A—C12A—C4A110.98 (11)C14C—C13C—H13G109.5
O4A—C13A—C14A111.17 (12)O4C—C13C—H13H109.5
O4A—C13A—H13C109.4C14C—C13C—H13H109.5
C14A—C13A—H13C109.4H13G—C13C—H13H108.1
O4A—C13A—H13D109.4C13C—C14C—H14J109.5
C14A—C13A—H13D109.4C13C—C14C—H14K109.5
H13C—C13A—H13D108.0H14J—C14C—H14K109.5
C13A—C14A—H14D109.5C13C—C14C—H14L109.5
C13A—C14A—H14E109.5H14J—C14C—H14L109.5
H14D—C14A—H14E109.5H14K—C14C—H14L109.5
C13A—C14A—H14F109.5C3D—O2D—H2D118.6 (15)
H14D—C14A—H14F109.5C12D—O4D—C13D115.86 (12)
H14E—C14A—H14F109.5C2D—N1D—C1D122.12 (12)
C3B—O2B—H2B110.7 (13)C2D—N1D—C5D113.71 (12)
C12B—O4B—C13B116.45 (11)C1D—N1D—C5D121.43 (12)
C2B—N1B—C1B122.08 (12)N1D—C1D—H1DA109.5
C2B—N1B—C5B113.31 (11)N1D—C1D—H1DB109.5
C1B—N1B—C5B121.34 (12)H1DA—C1D—H1DB109.5
N1B—C1B—H1BA109.5N1D—C1D—H1DC109.5
N1B—C1B—H1BB109.5H1DA—C1D—H1DC109.5
H1BA—C1B—H1BB109.5H1DB—C1D—H1DC109.5
N1B—C1B—H1BC109.5O1D—C2D—N1D125.38 (14)
H1BA—C1B—H1BC109.5O1D—C2D—C3D126.01 (13)
H1BB—C1B—H1BC109.5N1D—C2D—C3D108.56 (12)
O1B—C2B—N1B125.88 (13)O2D—C3D—C2D114.35 (12)
O1B—C2B—C3B125.36 (13)O2D—C3D—C4D115.37 (12)
N1B—C2B—C3B108.68 (12)C2D—C3D—C4D104.06 (11)
O2B—C3B—C2B113.30 (11)O2D—C3D—H3D107.6
O2B—C3B—C4B113.41 (11)C2D—C3D—H3D107.6
C2B—C3B—C4B103.35 (11)C4D—C3D—H3D107.6
O2B—C3B—H3B108.9C12D—C4D—C3D109.09 (11)
C2B—C3B—H3B108.9C12D—C4D—C5D111.68 (11)
C4B—C3B—H3B108.9C3D—C4D—C5D102.85 (11)
C12B—C4B—C3B109.14 (11)C12D—C4D—H4D111.0
C12B—C4B—C5B111.61 (11)C3D—C4D—H4D111.0
C3B—C4B—C5B102.60 (11)C5D—C4D—H4D111.0
C12B—C4B—H4B111.1N1D—C5D—C6D113.85 (11)
C3B—C4B—H4B111.1N1D—C5D—C4D102.67 (11)
C5B—C4B—H4B111.1C6D—C5D—C4D114.83 (11)
N1B—C5B—C6B114.30 (11)N1D—C5D—H5D108.4
N1B—C5B—C4B102.50 (11)C6D—C5D—H5D108.4
C6B—C5B—C4B114.38 (11)C4D—C5D—H5D108.4
N1B—C5B—H5B108.4C11D—C6D—C7D119.13 (13)
C6B—C5B—H5B108.4C11D—C6D—C5D122.66 (13)
C4B—C5B—H5B108.4C7D—C6D—C5D118.20 (13)
C7B—C6B—C11B118.98 (13)C8D—C7D—C6D120.30 (14)
C7B—C6B—C5B118.40 (12)C8D—C7D—H7D119.9
C11B—C6B—C5B122.58 (13)C6D—C7D—H7D119.9
C8B—C7B—C6B120.45 (14)C9D—C8D—C7D120.42 (14)
C8B—C7B—H7B119.8C9D—C8D—H8D119.8
C6B—C7B—H7B119.8C7D—C8D—H8D119.8
C9B—C8B—C7B120.20 (14)C8D—C9D—C10D119.51 (14)
C9B—C8B—H8B119.9C8D—C9D—H9D120.2
C7B—C8B—H8B119.9C10D—C9D—H9D120.2
C10B—C9B—C8B119.75 (14)C9D—C10D—C11D120.43 (14)
C10B—C9B—H9B120.1C9D—C10D—H10D119.8
C8B—C9B—H9B120.1C11D—C10D—H10D119.8
C9B—C10B—C11B120.32 (14)C10D—C11D—C6D120.20 (14)
C9B—C10B—H10B119.8C10D—C11D—H11D119.9
C11B—C10B—H10B119.8C6D—C11D—H11D119.9
C10B—C11B—C6B120.30 (14)O3D—C12D—O4D124.07 (13)
C10B—C11B—H11B119.9O3D—C12D—C4D124.25 (13)
C6B—C11B—H11B119.9O4D—C12D—C4D111.68 (12)
O3B—C12B—O4B124.07 (13)O4D—C13D—C14D110.86 (13)
O3B—C12B—C4B124.87 (13)O4D—C13D—H13A109.5
O4B—C12B—C4B111.06 (11)C14D—C13D—H13A109.5
O4B—C13B—C14B110.85 (13)O4D—C13D—H13B109.5
O4B—C13B—H13E109.5C14D—C13D—H13B109.5
C14B—C13B—H13E109.5H13A—C13D—H13B108.1
O4B—C13B—H13F109.5C13D—C14D—H14A109.5
C14B—C13B—H13F109.5C13D—C14D—H14B109.5
H13E—C13B—H13F108.1H14A—C14D—H14B109.5
C13B—C14B—H14G109.5C13D—C14D—H14C109.5
C13B—C14B—H14H109.5H14A—C14D—H14C109.5
H14G—C14B—H14H109.5H14B—C14D—H14C109.5
C13B—C14B—H14I109.5H5E—O5—H5F109.3 (16)
H14G—C14B—H14I109.5H6E—O6—H6F104.6 (14)
H14H—C14B—H14I109.5H7E—O7—H7F106.2 (15)
C3C—O2C—H2C108.5 (13)H8E—O8—H8F99.1 (14)
C12C—O4C—C13C116.09 (11)H9E—O9—H9F108.4 (16)
C2C—N1C—C1C122.91 (12)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O2A—H2A···O50.81 (2)1.86 (2)2.6569 (16)166 (2)
O2B—H2B···O1Bi0.84 (1)1.89 (2)2.7111 (14)165 (2)
O2C—H2C···O1Cii0.85 (1)1.89 (2)2.7089 (14)162 (2)
O2D—H2D···O8iii0.82 (2)1.92 (2)2.7134 (17)164 (2)
O5—H5E···O1Cii0.86 (1)1.94 (2)2.7857 (15)168 (2)
O5—H5F···O2Diii0.86 (1)1.79 (1)2.6490 (17)178 (2)
O6—H6F···O2Civ0.90 (1)1.99 (1)2.8837 (16)177 (2)
O6—H6E···O1Diii0.88 (1)1.96 (2)2.8218 (15)167 (2)
O7—H7F···O1A0.87 (1)1.97 (2)2.8399 (16)176 (2)
O7—H7E···O2Bv0.89 (1)2.01 (1)2.8987 (16)175 (2)
O8—H8E···O70.95 (2)1.87 (2)2.7637 (18)156 (2)
O8—H8F···O90.91 (1)1.93 (2)2.8193 (18)168 (2)
O9—H9F···O2A0.84 (2)1.98 (2)2.8199 (17)176 (2)
O9—H9E···O60.90 (1)1.93 (2)2.7724 (18)155 (2)
C3B—H3B···O1Avi1.002.453.2581 (17)138
C3C—H3C···O1D1.002.313.1537 (17)142
C3D—H3D···O1Diii1.002.563.4252 (18)145
C5A—H5A···O7v1.002.343.2374 (18)148
C5B—H5B···O9vi1.002.403.2568 (19)143
C5C—H5C···O8iii1.002.493.2395 (19)131
C5D—H5D···O61.002.413.2010 (18)135
C7A—H7A···O3B0.952.383.2943 (17)162
C7B—H7B···O3Avi0.952.463.3253 (18)151
C7C—H7C···O3D0.952.393.2704 (18)155
C11A—H11A···O4Biv0.952.543.3027 (17)138
Symmetry codes: (i) x, y, z+1; (ii) x, y+1, z+1; (iii) x+1, y+1, z+1; (iv) x+1, y, z; (v) x+1, y, z+1; (vi) x1, y, z.

Experimental details

Crystal data
Chemical formulaC14H17NO4·1.25H2O
Mr285.81
Crystal system, space groupTriclinic, P1
Temperature (K)100
a, b, c (Å)10.3669 (2), 15.7466 (3), 18.4539 (3)
α, β, γ (°)77.373 (1), 80.425 (1), 87.058 (1)
V3)2898.31 (9)
Z8
Radiation typeMo Kα
µ (mm1)0.10
Crystal size (mm)0.21 × 0.15 × 0.09
Data collection
DiffractometerBruker APEXII CCD
diffractometer
Absorption correctionMulti-scan
(SADABS; Sheldrick, 1996)
Tmin, Tmax0.979, 0.991
No. of measured, independent and
observed [I > 2σ(I)] reflections
22505, 11260, 9637
Rint0.018
(sin θ/λ)max1)0.617
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.039, 0.104, 1.02
No. of reflections11260
No. of parameters780
No. of restraints20
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)0.75, 0.28

Computer programs: APEX2 (Bruker, 2007), SAINT (Bruker, 2007), SHELXS97 (Sheldrick, 2008), X-SEED (Barbour, 2001), SHELXL97 (Sheldrick, 2008) and publCIF (Westrip, 2010).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O2A—H2A···O50.809 (15)1.864 (16)2.6569 (16)166 (2)
O2B—H2B···O1Bi0.842 (14)1.889 (15)2.7111 (14)164.7 (18)
O2C—H2C···O1Cii0.847 (14)1.889 (15)2.7089 (14)162.4 (18)
O2D—H2D···O8iii0.815 (15)1.919 (16)2.7134 (17)164 (2)
O5—H5E···O1Cii0.861 (14)1.938 (15)2.7857 (15)168 (2)
O5—H5F···O2Diii0.864 (14)1.785 (14)2.6490 (17)178 (2)
O6—H6F···O2Civ0.895 (14)1.989 (14)2.8837 (16)177 (2)
O6—H6E···O1Diii0.877 (14)1.961 (15)2.8218 (15)166.9 (19)
O7—H7F···O1A0.871 (14)1.970 (15)2.8399 (16)176 (2)
O7—H7E···O2Bv0.892 (14)2.009 (14)2.8987 (16)174.8 (18)
O8—H8E···O70.949 (15)1.870 (18)2.7637 (18)155.9 (18)
O8—H8F···O90.906 (14)1.927 (16)2.8193 (18)168 (2)
O9—H9F···O2A0.838 (15)1.983 (15)2.8199 (17)176 (2)
O9—H9E···O60.899 (14)1.932 (16)2.7724 (18)154.9 (19)
C3B—H3B···O1Avi1.002.453.2581 (17)138
C3C—H3C···O1D1.002.313.1537 (17)142
C3D—H3D···O1Diii1.002.563.4252 (18)145
C5A—H5A···O7v1.002.343.2374 (18)148
C5B—H5B···O9vi1.002.403.2568 (19)143
C5C—H5C···O8iii1.002.493.2395 (19)131
C5D—H5D···O61.002.413.2010 (18)135
C7A—H7A···O3B0.952.383.2943 (17)162
C7B—H7B···O3Avi0.952.463.3253 (18)151
C7C—H7C···O3D0.952.393.2704 (18)155
C11A—H11A···O4Biv0.952.543.3027 (17)138
Symmetry codes: (i) x, y, z+1; (ii) x, y+1, z+1; (iii) x+1, y+1, z+1; (iv) x+1, y, z; (v) x+1, y, z+1; (vi) x1, y, z.
 

Acknowledgements

The authors acknowledge the generous support of Universiti Teknologi MARA Malaysia (FRGS grant No. 600-RMI/ST/FRGS 5/3/Fst (11/2008) and the University of Malaya.

References

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First citationMa, D. & Jiang, J. (1998). Tetrahedron Asymmetry, 9, 575–579.  Web of Science CSD CrossRef CAS
First citationMohammat, M. F., Shaameri, Z. & Hamzah, A. S. (2009). Molecules, 14, 250–256.  Web of Science CrossRef PubMed CAS
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First citationWestrip, S. P. (2010). J. Appl. Cryst. 43, 920–925.  Web of Science CrossRef CAS IUCr Journals

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Volume 69| Part 2| February 2013| Pages o293-o294
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