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Crystals of L-leucylglycine (L-Leu–Gly) 0.67-hydrate, C8H16N2O3·0.67H2O, (I), were obtained from an aqueous solution. There are three symmetrically independent dipeptide zwitterionic mol­ecules in (I) and they are parallel to one another. The hydrogen-bond network composed of carboxyl­ate and amino groups and water mol­ecules extends parallel to the ab plane. Hydro­philic regions composed of main chains and hydro­phobic regions composed of the isobutyl groups of the leucyl residues are aligned alternately along the c axis. An imidazolidinone derivative was obtained from L-Leu–Gly and acetone, viz. [(4S)-2,2-dimethyl-4-(2-methyl­prop­yl)-5-oxo­imid­azolidin-3-ium-1-yl]acetate, C11H20N2O3, (II), and was crystallized from a methanol–acetone solution of L-Leu–Gly. The unit-cell parameters coincide with those reported previously for L-Leu–Gly dihydrate revealing that the previously reported values should be assigned to the structure of (II). One of the imidazolidine N atoms is protonated and the ring is nearly planar, except for the protonated N atom. Protonated N atoms and deprotonated carb­oxy groups of neighbouring mol­ecules form hydrogen-bonded chains. The ring carbonyl group is not involved in hydrogen bonding.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S010827011204810X/uk3056sup1.cif
Contains datablocks global, I, II

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S010827011204810X/uk3056Isup2.hkl
Contains datablock I

mol

MDL mol file https://doi.org/10.1107/S010827011204810X/uk3056Isup4.mol
Supplementary material

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S010827011204810X/uk3056IIsup3.hkl
Contains datablock II

mol

MDL mol file https://doi.org/10.1107/S010827011204810X/uk3056IIsup5.mol
Supplementary material

cml

Chemical Markup Language (CML) file https://doi.org/10.1107/S010827011204810X/uk3056IIsup6.cml
Supplementary material

CCDC references: 915103; 915104

Comment top

In living organisms, oligopeptides are produced from polypeptides by hydrolysis. A fair number of them are biologically active substances together with their derivatives. Among the dipeptides, the crystal structure of L-leucyl-glycine (L-Leu–Gly) has not been reported except for its cell parameters (Leonard & Pasternak, 1952). However, the cell parameters should be assigned to the crystal of the imidazolidinone derived from L-Leu–Gly (see below). We obtained crystals of L-Leu–Gly 0.67-hydrate, (I), from an aqueous solution. There are three L-Leu–Gly molecules (A, B and C) and two water molecules in an asymmetric unit (Fig. 1). The N-terminal and C-terminal groups of the three molecules are ionized. The backbones of molecules A, B and C are in extended forms parallel to the a axis. The conformation of the side chain of the leucyl group of molecule B is different from those of molecules A and C (Table 1). The conformation at N1—C1—C5—C6 of molecules A and C is trans, and that of molecule B is gauche-. The conformations at C1—C5—C6—C7 and C1—C5—C6—C8 of molecules A and C are trans and gauche+, respectively. On the other hand, the conformations of the corresponding parts of molecule B are trans and gauche-. The atomic displacement parameters of the side-chain atoms of leucyl residues are large. It is a general tendency that leucyl side-chain atoms, which are involved in van der Waals-type contacts and form hydrophobic regions in crystals, librate with large amplitude. Hydrogen-bonded chains between ionized carboxy and protonated amino groups extend parallel to the ab plane, partly intermediated by two water molecules, which exist every three L-Leu–Gly molecules (Fig. 2). One of the O—H bonds of the water molecules (O2W—H4W) forms a bifurcated hydrogen bond (Table 2). There are C—H···O interactions between the H atoms at the Cα positions of the leucyl residue and the carbonyl O atoms (C1A—H4A···O1B and C1B—H4B···O1C), and between the H atom at the Cα position of the glycyl residue and the carboxylate O atom (C3C—H6C···O2B). Two-dimensional sheets built from the hydrophilic parts of the main chains are paired by a twofold screw axis, which is parallel to the b axis (Fig. 3), and additional hydrogen bonds are formed between these sheets (Table 2). The paired sheets are isolated by hydrophobic regions composed of the isobutyl groups of the leucyl residues. As in the case of glycyl-L-leucine (Pattabhi et al., 1974), the hydrophobic and hydrophilic regions are aligned alternately along the c axis.

The crystal structure of D-leucylglycine hydrobromide (D-Leu–Gly.HBr) (Rao, 1969) is quite different from that of L-Leu–Gly 0.67-hydrate. In the case of D-Leu–Gly.HBr, the carboxyl groups are protonated and molecules related by a twofold screw axis form hydrogen-bonded chains involving protonated carboxy, carbonyl and protonated amino groups; one NH group and two NH3+ groups act as hydrogen-bond donors for Br-.

Topological analyses of hydrogen-bonding patterns in amino acids and oligopeptides in crystals have been reported based on searches of the Cambridge Structure Database (Allen, 2002). Görbitz (2010) classified dipeptides focusing on head-to-tail sequences connected by hydrogen bonds among the N-terminal amino and the C-terminal carboxyl groups. Glycyl-L-leucine belongs to the `T' group, where two peptides related by translational symmetry form a hydrogen bond between the N-terminal amino and the C-terminal carboxyl groups. L-Leu–Gly belongs to the same group. Görbitz also pays attention to the hydrogen-bonding arrangements of amide groups. In the case of L-Leu–Gly, however, there are no sequential hydrogen-bonding schemes among the amide groups, i.e. the N—H groups of molecules A and B form no hydrogen bonds, and that of molecule C acts as a hydrogen-bond donor for water atom O1W.

Imidazolidinones of oligopeptides are formed from compounds containing an α-aminoamide group, such as peptides with a free N-terminal amino group, and aldehydes or ketones. The parent peptides are released by hydrolysis in aqueous solution. Therefore, imidazolidinones of oligopeptides have been investigated as candidates for prodrugs (Sood & Panchagnula, 2001; Viso et al., 2005). One typical example is the imidazolidin-4-one of Leu-enkephalin (Rasmussen & Bundgaard, 1991). Although the synthesis and hydrolysis kinetics of the imidazolidinone derived from L-Leu–Gly and acetone, i.e. [(4S)-2,2-dimethyl-4-(2-methylpropyl)-5-oxoimidazolidin-1-yl] acetic acid, have already been investigated (Hardy & Samworth, 1977; Klixbüll & Bundgaard, 1984), the crystal structure of the compound has not been reported yet. By crystallizing L-Leu–Gly from a methanol–acetone solution, we obtained (II) (Fig. 4). The condensation reaction between L-Leu–Gly and acetone, which was used as the solvent, had proceeded, and the product crystallized. The cell parameters coincide with those reported for L-Leu–Gly dihydrate obtained from a water–acetone solution (Leonard & Pasternak, 1952). Therefore, Leonard & Pasternak had probably obtained (II).

The crystal system is triclinic and there is one molecule in the asymmetric unit. The carboxy group is deprotonated and the imidazolidine N atom at position 3 is protonated. The N1—C5 bond is a peptide bond and the atoms of the imidazolidinone ring (except for N3) are approximately on a plane together with oxo atom O5 (Table 3). As in the case of (I), the hydrophilic and hydrophobic regions are aligned alternately along the c axis. In the hydrophilic regions, carboxylate groups and protonated N atoms form hydrogen-bonded chains (Fig. 5). The carbonyl group is not involved hydrogen bonding.

Related literature top

For related literature, see: Allen (2002); Görbitz (2010); Hardy & Samworth (1977); Klixbüll & Bundgaard (1984); Leonard & Pasternak (1952); Pattabhi et al. (1974); Rao (1969); Rasmussen & Bundgaard (1991); Sood & Panchagnula (2001); Viso et al. (2005).

Experimental top

L-Leu–Gly was purchased from Peptide Institute Inc. Crystals of (I) were obtained from an aqueous solution and crystals of (II) were obtained from a water–acetone solution according to the literature method of Leonard & Pasternak (1952). The cell parameters coincided with the reported values. However, the quality of the crystals was insufficient for structure analysis. After employing several organic solvents, we obtained crystals of (II) suitable for single-crystal X-ray analysis by the slow vapor diffusion method using methanol as solvent and acetone as precipitant.

Refinement top

H atoms were initially located on a difference Fourier map and then placed at calculated positions, with C—H = 0.96 (CH3), 0.97 (CH2) or 0.98 Å (CH), O—H = 0.82 Å and N—H = 0.87 (NH3, NH) or N—H = 0.90 Å (NH2), and were allowed to ride on the atom to which they were attached, with Uiso(H) = 1.2Ueq(C,N,O) except for methyl groups in (I) with Uiso(H) = 1.5Ueq(C). The absolute configuration was known for the purchased material.

Computing details top

For both compounds, data collection: CrystalClear (Rigaku/MSC, 2006); cell refinement: CrystalClear (Rigaku/MSC, 2006); data reduction: CrystalClear (Rigaku/MSC, 2006); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: Mercury (Macrae et al., 2006); software used to prepare material for publication: Yadokari-XG 2009 (Kabuto et al., 2009).

Figures top
[Figure 1] Fig. 1. The asymmetric unit of (I), showing the atom-numbering scheme. Displacement ellipsoids are drawn at the 50% probability level.
[Figure 2] Fig. 2. The hydrogen-bonding networks within a sheet of hydrophilic moieties in (I), viewed along the c axis. Darker dashed lines (blue in the electronic version of the paper) indicate hydrogen bonds and lighter dashed lines indicate C—H···O interactions. Side-chain atoms of the leucyl residues have been omitted for clarity.
[Figure 3] Fig. 3. Crystal packing of (I) viewed along the a axis. Light-blue and blue dashed lines indicate intralayer and interlayer hydrogen bonds.
[Figure 4] Fig. 4. The molecular structure of (II), showing the atom-numbering scheme. Displacement ellipsoids are drawn at the 50% probability level.
[Figure 5] Fig. 5. The crystal packing of (II), viewed along the b axis. Dashed lines are intermolecular hydrogen bonds.
(I) L-Leucylglycine 0.67-hydrate top
Crystal data top
3C8H16N2O3·2H2OF(000) = 1304
Mr = 600.72Dx = 1.213 Mg m3
Orthorhombic, P212121Mo Kα radiation, λ = 0.71070 Å
Hall symbol: P 2ac 2abCell parameters from 1539 reflections
a = 8.735 (5) Åθ = 10.0–15.0°
b = 15.54 (1) ŵ = 0.10 mm1
c = 24.238 (15) ÅT = 299 K
V = 3290 (4) Å3Needle, colorless
Z = 40.49 × 0.07 × 0.02 mm
Data collection top
Rigaku Mercury CCD area-detector
diffractometer
4707 reflections with I > 2σ(I)
Radiation source: rotating anodeRint = 0.064
Graphite monochromatorθmax = 25.0°, θmin = 2.6°
ω scansh = 1010
21778 measured reflectionsk = 1618
5794 independent reflectionsl = 2828
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)] = 0.060Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.161H-atom parameters constrained
S = 1.09 w = 1/[σ2(Fo2) + (0.0719P)2 + 0.4708P]
where P = (Fo2 + 2Fc2)/3
5794 reflections(Δ/σ)max < 0.001
370 parametersΔρmax = 0.26 e Å3
0 restraintsΔρmin = 0.19 e Å3
Crystal data top
3C8H16N2O3·2H2OV = 3290 (4) Å3
Mr = 600.72Z = 4
Orthorhombic, P212121Mo Kα radiation
a = 8.735 (5) ŵ = 0.10 mm1
b = 15.54 (1) ÅT = 299 K
c = 24.238 (15) Å0.49 × 0.07 × 0.02 mm
Data collection top
Rigaku Mercury CCD area-detector
diffractometer
4707 reflections with I > 2σ(I)
21778 measured reflectionsRint = 0.064
5794 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0600 restraints
wR(F2) = 0.161H-atom parameters constrained
S = 1.09Δρmax = 0.26 e Å3
5794 reflectionsΔρmin = 0.19 e Å3
370 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
N1A1.0573 (3)0.08948 (17)0.22525 (11)0.0431 (6)
H1A1.11850.04610.23060.052*
H2A1.01870.10570.25670.052*
H3A1.10810.13190.21070.052*
C1A0.9316 (3)0.06326 (19)0.18740 (13)0.0417 (7)
H4A0.87230.11390.17620.050*
C2A0.8291 (3)0.0000 (2)0.21743 (15)0.0433 (8)
O1A0.8828 (3)0.06594 (14)0.23804 (11)0.0560 (6)
N2A0.6805 (3)0.01804 (17)0.21830 (12)0.0446 (7)
H5A0.64930.06700.20510.054*
C3A0.5684 (3)0.0416 (2)0.24070 (16)0.0508 (9)
H6A0.60140.06060.27690.061*
H7A0.56190.09180.21700.061*
C4A0.4114 (3)0.0000 (2)0.24524 (13)0.0429 (7)
O2A0.4058 (3)0.07911 (15)0.24817 (11)0.0551 (6)
O3A0.2970 (2)0.04994 (16)0.24721 (11)0.0555 (6)
C5A1.0049 (4)0.0211 (2)0.13664 (14)0.0527 (8)
H8A1.07000.06310.11860.063*
H9A1.06980.02580.14900.063*
C6A0.8914 (5)0.0141 (2)0.09418 (16)0.0632 (10)
H10A0.82230.05400.11320.076*
C7A0.9768 (7)0.0644 (4)0.0503 (2)0.1026 (18)
H11A1.03320.02530.02730.154*
H12A0.90490.09590.02810.154*
H13A1.04630.10390.06760.154*
C8A0.7938 (7)0.0571 (4)0.0682 (2)0.1041 (19)
H14A0.85790.09380.04620.156*
H15A0.74610.09030.09680.156*
H16A0.71650.03170.04520.156*
N1B0.8991 (3)0.36914 (16)0.16818 (12)0.0446 (6)
H1B0.95680.32380.17140.053*
H2B0.86350.38350.20040.053*
H3B0.95270.41150.15480.053*
C1B0.7695 (3)0.3498 (2)0.13038 (13)0.0396 (7)
H4B0.71660.40330.12050.048*
C2B0.6590 (3)0.2893 (2)0.15932 (14)0.0412 (7)
O1B0.7080 (2)0.23040 (15)0.18869 (11)0.0539 (6)
N2B0.5129 (3)0.30142 (18)0.14888 (12)0.0495 (7)
H5B0.48680.34450.12800.059*
C3B0.3929 (4)0.2463 (2)0.17050 (17)0.0570 (10)
H6B0.40350.24150.21020.068*
H7B0.40280.18910.15480.068*
C4B0.2370 (4)0.2825 (2)0.15667 (16)0.0479 (8)
O2B0.2294 (3)0.34832 (16)0.12942 (13)0.0676 (8)
O3B0.1240 (3)0.23989 (14)0.17583 (12)0.0581 (7)
C5B0.8285 (4)0.3060 (2)0.07844 (14)0.0499 (8)
H8B0.89440.25890.08970.060*
H9B0.74150.28100.05940.060*
C6B0.9157 (5)0.3603 (2)0.03750 (16)0.0615 (10)
H10B1.00000.38890.05690.074*
C7B0.9838 (7)0.3005 (4)0.0066 (2)0.111 (2)
H11B0.90290.26930.02440.167*
H12B1.05300.26060.01060.167*
H13B1.03820.33410.03340.167*
C8B0.8168 (7)0.4282 (3)0.0112 (2)0.0965 (17)
H14B0.73050.40140.00620.145*
H15B0.87540.45900.01590.145*
H16B0.78150.46750.03900.145*
N1C0.7393 (3)0.64922 (17)0.16174 (12)0.0475 (7)
H1C0.78760.60930.14350.057*
H2C0.70830.62860.19320.057*
H3C0.80060.69240.16760.057*
C1C0.6045 (3)0.6789 (2)0.12904 (14)0.0452 (8)
H4C0.54800.72200.15040.054*
C2C0.5012 (4)0.6013 (2)0.11892 (14)0.0433 (7)
O1C0.5564 (3)0.53145 (16)0.10786 (12)0.0644 (7)
N2C0.3524 (3)0.61679 (17)0.12288 (12)0.0470 (7)
H5C0.32280.66850.13170.056*
C3C0.2364 (3)0.5514 (2)0.11324 (15)0.0444 (8)
H6C0.27480.49590.12530.053*
H7C0.21510.54780.07400.053*
C4C0.0904 (3)0.57185 (19)0.14379 (14)0.0427 (7)
O2C0.0972 (3)0.62780 (15)0.18099 (11)0.0597 (7)
O3C0.0279 (2)0.53187 (15)0.12990 (11)0.0573 (7)
C5C0.6583 (4)0.7193 (3)0.07484 (16)0.0566 (9)
H8C0.74070.75920.08290.068*
H9C0.69990.67420.05160.068*
C6C0.5353 (4)0.7667 (3)0.04268 (17)0.0648 (11)
H10C0.45050.72660.03630.078*
C7C0.5985 (6)0.7938 (4)0.0138 (2)0.0931 (16)
H11C0.52140.82520.03360.140*
H12C0.62670.74350.03440.140*
H13C0.68690.82970.00870.140*
C8C0.4728 (6)0.8435 (3)0.0731 (2)0.0927 (16)
H14C0.40980.82430.10310.139*
H15C0.41280.87790.04830.139*
H16C0.55610.87720.08720.139*
O1W0.2869 (5)0.7849 (2)0.19550 (13)0.0965 (12)
H1W0.29170.83290.20940.116*
H2W0.28740.75190.22190.116*
O2W0.0671 (4)0.78829 (18)0.17455 (15)0.0847 (10)
H3W0.07800.83230.19280.102*
H4W0.02470.77900.17070.102*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N1A0.0290 (12)0.0434 (14)0.0570 (16)0.0021 (11)0.0062 (12)0.0015 (12)
C1A0.0288 (14)0.0379 (16)0.0585 (19)0.0060 (13)0.0041 (14)0.0018 (14)
C2A0.0283 (15)0.0380 (18)0.063 (2)0.0034 (13)0.0034 (15)0.0016 (15)
O1A0.0377 (12)0.0393 (12)0.0910 (19)0.0023 (10)0.0034 (12)0.0178 (12)
N2A0.0246 (12)0.0390 (15)0.0703 (18)0.0015 (10)0.0073 (12)0.0041 (13)
C3A0.0269 (15)0.0441 (18)0.081 (2)0.0075 (14)0.0099 (16)0.0007 (17)
C4A0.0266 (15)0.051 (2)0.0509 (18)0.0000 (13)0.0055 (14)0.0033 (15)
O2A0.0434 (13)0.0446 (14)0.0774 (16)0.0035 (11)0.0092 (13)0.0047 (12)
O3A0.0305 (12)0.0581 (15)0.0780 (16)0.0094 (10)0.0065 (11)0.0012 (13)
C5A0.0448 (19)0.053 (2)0.060 (2)0.0053 (16)0.0107 (17)0.0062 (16)
C6A0.066 (3)0.058 (2)0.065 (2)0.0145 (19)0.002 (2)0.0105 (18)
C7A0.113 (4)0.107 (4)0.088 (3)0.020 (3)0.017 (3)0.040 (3)
C8A0.131 (5)0.088 (4)0.094 (4)0.009 (3)0.048 (4)0.007 (3)
N1B0.0290 (13)0.0397 (14)0.0651 (17)0.0066 (11)0.0015 (12)0.0047 (12)
C1B0.0269 (14)0.0348 (16)0.0572 (19)0.0010 (12)0.0054 (14)0.0004 (14)
C2B0.0293 (15)0.0368 (17)0.0574 (19)0.0002 (12)0.0029 (14)0.0013 (15)
O1B0.0343 (12)0.0479 (14)0.0794 (17)0.0032 (10)0.0015 (12)0.0158 (12)
N2B0.0280 (13)0.0490 (16)0.0716 (19)0.0017 (12)0.0005 (13)0.0186 (14)
C3B0.0275 (16)0.056 (2)0.088 (3)0.0059 (15)0.0034 (17)0.0253 (19)
C4B0.0277 (16)0.0400 (18)0.076 (2)0.0030 (13)0.0011 (16)0.0032 (17)
O2B0.0377 (13)0.0530 (15)0.112 (2)0.0001 (11)0.0033 (14)0.0335 (15)
O3B0.0288 (11)0.0460 (13)0.0995 (19)0.0047 (10)0.0057 (12)0.0145 (13)
C5B0.0448 (19)0.0465 (19)0.058 (2)0.0029 (15)0.0078 (16)0.0036 (16)
C6B0.055 (2)0.058 (2)0.072 (2)0.0055 (19)0.016 (2)0.0012 (18)
C7B0.137 (5)0.093 (4)0.104 (4)0.011 (3)0.068 (4)0.001 (3)
C8B0.119 (4)0.095 (4)0.075 (3)0.021 (3)0.022 (3)0.020 (3)
N1C0.0323 (14)0.0434 (15)0.0667 (18)0.0008 (12)0.0013 (13)0.0030 (13)
C1C0.0276 (15)0.0418 (17)0.066 (2)0.0003 (13)0.0047 (15)0.0043 (15)
C2C0.0260 (15)0.0425 (19)0.061 (2)0.0023 (13)0.0022 (15)0.0043 (15)
O1C0.0395 (13)0.0491 (14)0.105 (2)0.0063 (12)0.0022 (13)0.0177 (14)
N2C0.0302 (13)0.0367 (14)0.0740 (19)0.0026 (11)0.0070 (13)0.0015 (13)
C3C0.0334 (16)0.0369 (17)0.063 (2)0.0034 (13)0.0022 (15)0.0006 (14)
C4C0.0303 (15)0.0369 (16)0.061 (2)0.0028 (13)0.0021 (14)0.0089 (15)
O2C0.0493 (14)0.0533 (15)0.0767 (17)0.0097 (12)0.0191 (13)0.0120 (13)
O3C0.0317 (12)0.0440 (13)0.0961 (19)0.0040 (10)0.0020 (12)0.0019 (13)
C5C0.0375 (18)0.064 (2)0.068 (2)0.0065 (17)0.0053 (17)0.0160 (18)
C6C0.047 (2)0.071 (3)0.077 (3)0.0085 (18)0.0033 (18)0.024 (2)
C7C0.077 (3)0.119 (4)0.083 (3)0.018 (3)0.000 (3)0.041 (3)
C8C0.090 (4)0.081 (3)0.107 (4)0.016 (3)0.004 (3)0.034 (3)
O1W0.146 (3)0.0593 (18)0.085 (2)0.022 (2)0.024 (2)0.0098 (16)
O2W0.0697 (19)0.0504 (15)0.134 (3)0.0020 (14)0.023 (2)0.0157 (16)
Geometric parameters (Å, º) top
N1A—C1A1.487 (4)C5B—C6B1.509 (5)
N1A—H1A0.8700C5B—H8B0.9700
N1A—H2A0.8700C5B—H9B0.9700
N1A—H3A0.8700C6B—C8B1.505 (6)
C1A—C2A1.516 (4)C6B—C7B1.536 (6)
C1A—C5A1.534 (5)C6B—H10B0.9800
C1A—H4A0.9800C7B—H11B0.9600
C2A—O1A1.232 (4)C7B—H12B0.9600
C2A—N2A1.329 (4)C7B—H13B0.9600
N2A—C3A1.453 (4)C8B—H14B0.9600
N2A—H5A0.8700C8B—H15B0.9600
C3A—C4A1.521 (4)C8B—H16B0.9600
C3A—H6A0.9700N1C—C1C1.493 (4)
C3A—H7A0.9700N1C—H1C0.8700
C4A—O2A1.232 (4)N1C—H2C0.8700
C4A—O3A1.266 (4)N1C—H3C0.8700
C5A—C6A1.530 (5)C1C—C2C1.525 (4)
C5A—H8A0.9700C1C—C5C1.530 (5)
C5A—H9A0.9700C1C—H4C0.9800
C6A—C7A1.516 (6)C2C—O1C1.218 (4)
C6A—C8A1.532 (6)C2C—N2C1.325 (4)
C6A—H10A0.9800N2C—C3C1.454 (4)
C7A—H11A0.9600N2C—H5C0.8700
C7A—H12A0.9600C3C—C4C1.508 (4)
C7A—H13A0.9600C3C—H6C0.9700
C8A—H14A0.9600C3C—H7C0.9700
C8A—H15A0.9600C4C—O3C1.252 (4)
C8A—H16A0.9600C4C—O2C1.254 (4)
N1B—C1B1.487 (4)C5C—C6C1.518 (5)
N1B—H1B0.8700C5C—H8C0.9700
N1B—H2B0.8700C5C—H9C0.9700
N1B—H3B0.8700C6C—C8C1.504 (7)
C1B—C2B1.519 (4)C6C—C7C1.534 (6)
C1B—C5B1.521 (5)C6C—H10C0.9800
C1B—H4B0.9800C7C—H11C0.9600
C2B—O1B1.237 (4)C7C—H12C0.9600
C2B—N2B1.314 (4)C7C—H13C0.9600
N2B—C3B1.452 (4)C8C—H14C0.9600
N2B—H5B0.8700C8C—H15C0.9600
C3B—C4B1.512 (4)C8C—H16C0.9600
C3B—H6B0.9700O1W—H1W0.8198
C3B—H7B0.9700O1W—H2W0.8200
C4B—O2B1.219 (4)O2W—H3W0.8200
C4B—O3B1.277 (4)O2W—H4W0.8202
C1A—N1A—H1A109.5C6B—C5B—C1B117.7 (3)
C1A—N1A—H2A109.5C6B—C5B—H8B107.9
H1A—N1A—H2A109.5C1B—C5B—H8B107.9
C1A—N1A—H3A109.5C6B—C5B—H9B107.9
H1A—N1A—H3A109.5C1B—C5B—H9B107.9
H2A—N1A—H3A109.5H8B—C5B—H9B107.2
N1A—C1A—C2A108.5 (3)C8B—C6B—C5B112.4 (4)
N1A—C1A—C5A107.7 (3)C8B—C6B—C7B110.6 (4)
C2A—C1A—C5A110.7 (3)C5B—C6B—C7B108.3 (3)
N1A—C1A—H4A110.0C8B—C6B—H10B108.5
C2A—C1A—H4A110.0C5B—C6B—H10B108.5
C5A—C1A—H4A110.0C7B—C6B—H10B108.5
O1A—C2A—N2A122.7 (3)C6B—C7B—H11B109.5
O1A—C2A—C1A120.6 (3)C6B—C7B—H12B109.5
N2A—C2A—C1A116.6 (3)H11B—C7B—H12B109.5
C2A—N2A—C3A122.0 (3)C6B—C7B—H13B109.5
C2A—N2A—H5A119.0H11B—C7B—H13B109.5
C3A—N2A—H5A119.0H12B—C7B—H13B109.5
N2A—C3A—C4A111.3 (3)C6B—C8B—H14B109.5
N2A—C3A—H6A109.4C6B—C8B—H15B109.5
C4A—C3A—H6A109.4H14B—C8B—H15B109.5
N2A—C3A—H7A109.4C6B—C8B—H16B109.5
C4A—C3A—H7A109.4H14B—C8B—H16B109.5
H6A—C3A—H7A108.0H15B—C8B—H16B109.5
O2A—C4A—O3A125.3 (3)C1C—N1C—H1C109.5
O2A—C4A—C3A117.7 (3)C1C—N1C—H2C109.5
O3A—C4A—C3A117.0 (3)H1C—N1C—H2C109.5
C6A—C5A—C1A115.0 (3)C1C—N1C—H3C109.5
C6A—C5A—H8A108.5H1C—N1C—H3C109.5
C1A—C5A—H8A108.5H2C—N1C—H3C109.5
C6A—C5A—H9A108.5N1C—C1C—C2C107.9 (2)
C1A—C5A—H9A108.5N1C—C1C—C5C109.9 (3)
H8A—C5A—H9A107.5C2C—C1C—C5C111.6 (3)
C7A—C6A—C5A109.7 (4)N1C—C1C—H4C109.1
C7A—C6A—C8A110.9 (4)C2C—C1C—H4C109.1
C5A—C6A—C8A112.3 (3)C5C—C1C—H4C109.1
C7A—C6A—H10A107.9O1C—C2C—N2C124.5 (3)
C5A—C6A—H10A107.9O1C—C2C—C1C120.4 (3)
C8A—C6A—H10A107.9N2C—C2C—C1C115.2 (3)
C6A—C7A—H11A109.5C2C—N2C—C3C123.1 (3)
C6A—C7A—H12A109.5C2C—N2C—H5C118.5
H11A—C7A—H12A109.5C3C—N2C—H5C118.5
C6A—C7A—H13A109.5N2C—C3C—C4C111.3 (3)
H11A—C7A—H13A109.5N2C—C3C—H6C109.4
H12A—C7A—H13A109.5C4C—C3C—H6C109.4
C6A—C8A—H14A109.5N2C—C3C—H7C109.4
C6A—C8A—H15A109.5C4C—C3C—H7C109.4
H14A—C8A—H15A109.5H6C—C3C—H7C108.0
C6A—C8A—H16A109.5O3C—C4C—O2C125.2 (3)
H14A—C8A—H16A109.5O3C—C4C—C3C117.5 (3)
H15A—C8A—H16A109.5O2C—C4C—C3C117.3 (3)
C1B—N1B—H1B109.5C6C—C5C—C1C115.0 (3)
C1B—N1B—H2B109.5C6C—C5C—H8C108.5
H1B—N1B—H2B109.5C1C—C5C—H8C108.5
C1B—N1B—H3B109.5C6C—C5C—H9C108.5
H1B—N1B—H3B109.5C1C—C5C—H9C108.5
H2B—N1B—H3B109.5H8C—C5C—H9C107.5
N1B—C1B—C2B108.9 (3)C8C—C6C—C5C113.0 (4)
N1B—C1B—C5B110.0 (3)C8C—C6C—C7C110.5 (4)
C2B—C1B—C5B108.7 (3)C5C—C6C—C7C109.7 (4)
N1B—C1B—H4B109.7C8C—C6C—H10C107.8
C2B—C1B—H4B109.7C5C—C6C—H10C107.8
C5B—C1B—H4B109.7C7C—C6C—H10C107.8
O1B—C2B—N2B123.6 (3)C6C—C7C—H11C109.5
O1B—C2B—C1B120.3 (3)C6C—C7C—H12C109.5
N2B—C2B—C1B116.1 (3)H11C—C7C—H12C109.5
C2B—N2B—C3B123.2 (3)C6C—C7C—H13C109.5
C2B—N2B—H5B118.4H11C—C7C—H13C109.5
C3B—N2B—H5B118.4H12C—C7C—H13C109.5
N2B—C3B—C4B110.5 (3)C6C—C8C—H14C109.5
N2B—C3B—H6B109.5C6C—C8C—H15C109.5
C4B—C3B—H6B109.5H14C—C8C—H15C109.5
N2B—C3B—H7B109.5C6C—C8C—H16C109.5
C4B—C3B—H7B109.5H14C—C8C—H16C109.5
H6B—C3B—H7B108.1H15C—C8C—H16C109.5
O2B—C4B—O3B126.2 (3)H1W—O1W—H2W104.4
O2B—C4B—C3B118.8 (3)H3W—O2W—H4W108.7
O3B—C4B—C3B115.0 (3)
N1A—C1A—C2A—O1A55.3 (4)N2B—C3B—C4B—O2B1.9 (5)
C5A—C1A—C2A—O1A62.7 (4)N2B—C3B—C4B—O3B177.5 (3)
N1A—C1A—C2A—N2A127.1 (3)N1B—C1B—C5B—C6B72.4 (4)
C5A—C1A—C2A—N2A114.9 (3)C2B—C1B—C5B—C6B168.4 (3)
O1A—C2A—N2A—C3A4.0 (5)C1B—C5B—C6B—C8B65.9 (5)
C1A—C2A—N2A—C3A173.6 (3)C1B—C5B—C6B—C7B171.6 (4)
C2A—N2A—C3A—C4A170.8 (3)N1C—C1C—C2C—O1C40.2 (4)
N2A—C3A—C4A—O2A23.5 (5)C5C—C1C—C2C—O1C80.6 (4)
N2A—C3A—C4A—O3A158.4 (3)N1C—C1C—C2C—N2C140.1 (3)
N1A—C1A—C5A—C6A177.2 (3)C5C—C1C—C2C—N2C99.1 (4)
C2A—C1A—C5A—C6A58.7 (4)O1C—C2C—N2C—C3C1.3 (6)
C1A—C5A—C6A—C7A172.4 (4)C1C—C2C—N2C—C3C178.4 (3)
C1A—C5A—C6A—C8A63.8 (5)C2C—N2C—C3C—C4C154.5 (3)
N1B—C1B—C2B—O1B39.3 (4)N2C—C3C—C4C—O3C164.8 (3)
C5B—C1B—C2B—O1B80.6 (4)N2C—C3C—C4C—O2C14.9 (4)
N1B—C1B—C2B—N2B143.9 (3)N1C—C1C—C5C—C6C169.2 (3)
C5B—C1B—C2B—N2B96.3 (4)C2C—C1C—C5C—C6C71.1 (4)
O1B—C2B—N2B—C3B0.4 (6)C1C—C5C—C6C—C8C63.5 (5)
C1B—C2B—N2B—C3B176.3 (3)C1C—C5C—C6C—C7C172.7 (4)
C2B—N2B—C3B—C4B173.5 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1A—H1A···O3Ai0.872.203.060 (4)172
N1A—H2A···O2Cii0.871.852.709 (4)169
N1A—H3A···O3Bi0.871.882.690 (4)154
N1B—H1B···O3Bi0.871.962.816 (4)167
N1B—H2B···O3Aiii0.872.162.953 (4)152
N1B—H3B···O3Ci0.871.972.768 (4)151
N1C—H1C···O3Ci0.872.042.838 (4)152
N1C—H2C···O2Aiii0.871.902.750 (4)166
N1C—H3C···O2Wi0.871.892.762 (5)176
N2C—H5C···O1W0.872.403.202 (5)153
O1W—H1W···O3Aiv0.822.042.857 (5)177
O1W—H2W···O1Biii0.822.192.933 (5)150
O2W—H3W···O1Av0.821.962.773 (5)176
O2W—H4W···O1W0.822.373.134 (5)156
O2W—H4W···O2C0.822.452.882 (5)114
C1A—H4A···O1B0.982.333.250 (4)156
C1B—H4B···O1C0.982.453.425 (4)171
C3C—H6C···O2B0.972.333.181 (5)146
Symmetry codes: (i) x+1, y, z; (ii) x+1, y1/2, z+1/2; (iii) x+1, y+1/2, z+1/2; (iv) x, y+1, z; (v) x1, y+1, z.
(II) [(4S)-2,2-dimethyl-4-(2-methylpropyl)- 5-oxoimidazolidin-3-ium-1-yl]acetate top
Crystal data top
C11H20N2O3Z = 1
Mr = 228.29F(000) = 124
Triclinic, P1Dx = 1.219 Mg m3
Hall symbol: P 1Mo Kα radiation, λ = 0.71070 Å
a = 6.0060 (14) ÅCell parameters from 871 reflections
b = 6.8782 (18) Åθ = 5.4–25.0°
c = 7.9717 (18) ŵ = 0.09 mm1
α = 90.202 (11)°T = 298 K
β = 98.272 (8)°Plate, colorless
γ = 107.193 (11)°0.60 × 0.55 × 0.04 mm
V = 310.96 (13) Å3
Data collection top
Rigaku Mercury CCD area-detector
diffractometer
2526 independent reflections
Radiation source: rotating anode2501 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.013
Detector resolution: 14.2959 pixels mm-1θmax = 27.5°, θmin = 3.1°
ω scansh = 77
Absorption correction: multi-scan
(CrystalClear; Rigaku/MSC, 2006)
k = 88
Tmin = 0.661, Tmax = 1.000l = 1010
3600 measured reflections
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)] = 0.034Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.093H-atom parameters constrained
S = 1.04 w = 1/[σ2(Fo2) + (0.0586P)2 + 0.0404P]
where P = (Fo2 + 2Fc2)/3
2526 reflections(Δ/σ)max < 0.001
149 parametersΔρmax = 0.17 e Å3
3 restraintsΔρmin = 0.15 e Å3
Crystal data top
C11H20N2O3γ = 107.193 (11)°
Mr = 228.29V = 310.96 (13) Å3
Triclinic, P1Z = 1
a = 6.0060 (14) ÅMo Kα radiation
b = 6.8782 (18) ŵ = 0.09 mm1
c = 7.9717 (18) ÅT = 298 K
α = 90.202 (11)°0.60 × 0.55 × 0.04 mm
β = 98.272 (8)°
Data collection top
Rigaku Mercury CCD area-detector
diffractometer
2526 independent reflections
Absorption correction: multi-scan
(CrystalClear; Rigaku/MSC, 2006)
2501 reflections with I > 2σ(I)
Tmin = 0.661, Tmax = 1.000Rint = 0.013
3600 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0343 restraints
wR(F2) = 0.093H-atom parameters constrained
S = 1.04Δρmax = 0.17 e Å3
2526 reflectionsΔρmin = 0.15 e Å3
149 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
N10.89234 (19)0.34603 (16)0.50248 (15)0.0294 (2)
C21.0403 (2)0.48160 (19)0.39433 (17)0.0289 (3)
N31.16888 (18)0.65959 (15)0.51877 (14)0.0259 (2)
H3A1.31700.71530.49740.031*
H3B1.09420.75570.50910.031*
C41.1729 (2)0.5814 (2)0.69338 (17)0.0319 (3)
H41.31620.54090.72450.038*
C50.9605 (3)0.3930 (2)0.67005 (19)0.0355 (3)
O50.8677 (3)0.2983 (2)0.78350 (17)0.0605 (4)
C60.7115 (2)0.1578 (2)0.4436 (2)0.0351 (3)
H6A0.66360.16270.32260.042*
H6B0.57520.14840.49880.042*
C70.7863 (2)0.0356 (2)0.47641 (18)0.0308 (3)
O7A1.00096 (18)0.01889 (16)0.49825 (17)0.0444 (3)
O7B0.62318 (19)0.19790 (16)0.47462 (18)0.0469 (3)
C81.1626 (3)0.7353 (3)0.82590 (19)0.0382 (3)
H8A1.13230.66620.92990.046*
H8B1.03020.78580.78740.046*
C91.3845 (3)0.9170 (2)0.86607 (19)0.0392 (3)
H91.42860.97300.75860.047*
C101.5902 (4)0.8572 (4)0.9603 (3)0.0627 (5)
H10A1.72680.97470.97990.075*
H10B1.62250.75500.89360.075*
H10C1.55150.80391.06710.075*
C111.3345 (4)1.0817 (4)0.9684 (3)0.0659 (6)
H11A1.30151.03301.07760.079*
H11B1.20081.11540.90950.079*
H11C1.46951.20070.98290.079*
C211.2178 (3)0.3901 (3)0.3314 (3)0.0460 (4)
H21A1.31310.35500.42670.055*
H21B1.31680.48780.26710.055*
H21C1.13490.26990.26060.055*
C220.8964 (3)0.5542 (3)0.24924 (19)0.0404 (3)
H22A0.82970.44660.16310.048*
H22B0.99640.67000.20200.048*
H22C0.77200.59200.29090.048*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N10.0284 (5)0.0175 (5)0.0422 (6)0.0051 (4)0.0084 (4)0.0028 (4)
C20.0286 (6)0.0200 (6)0.0393 (7)0.0066 (5)0.0110 (5)0.0003 (5)
N30.0240 (5)0.0191 (5)0.0364 (5)0.0071 (4)0.0090 (4)0.0029 (4)
C40.0298 (6)0.0287 (7)0.0372 (7)0.0081 (5)0.0063 (5)0.0059 (5)
C50.0378 (7)0.0261 (7)0.0423 (7)0.0069 (6)0.0107 (6)0.0094 (5)
O50.0680 (8)0.0503 (8)0.0520 (7)0.0041 (6)0.0191 (6)0.0172 (6)
C60.0254 (6)0.0203 (6)0.0578 (8)0.0062 (5)0.0024 (6)0.0039 (6)
C70.0280 (6)0.0189 (6)0.0458 (7)0.0059 (5)0.0091 (5)0.0009 (5)
O7A0.0281 (5)0.0238 (5)0.0819 (8)0.0104 (4)0.0048 (5)0.0047 (5)
O7B0.0343 (6)0.0211 (5)0.0859 (9)0.0026 (4)0.0238 (6)0.0004 (5)
C80.0367 (7)0.0425 (8)0.0341 (6)0.0076 (6)0.0100 (6)0.0004 (6)
C90.0392 (7)0.0384 (8)0.0350 (6)0.0054 (6)0.0034 (6)0.0005 (6)
C100.0426 (9)0.0673 (14)0.0731 (13)0.0155 (9)0.0057 (9)0.0028 (10)
C110.0676 (13)0.0549 (12)0.0697 (12)0.0181 (10)0.0065 (10)0.0214 (10)
C210.0414 (8)0.0323 (8)0.0697 (10)0.0114 (6)0.0255 (8)0.0075 (7)
C220.0463 (9)0.0368 (8)0.0352 (7)0.0089 (6)0.0047 (6)0.0028 (6)
Geometric parameters (Å, º) top
N1—C51.3482 (19)C8—C91.527 (2)
N1—C61.4469 (17)C8—H8A0.9700
N1—C21.4624 (17)C8—H8B0.9700
C2—N31.5137 (17)C9—C101.515 (2)
C2—C221.5186 (19)C9—C111.518 (3)
C2—C211.5275 (19)C9—H90.9800
N3—C41.4935 (17)C10—H10A0.9600
N3—H3A0.9000C10—H10B0.9600
N3—H3B0.9000C10—H10C0.9600
C4—C81.513 (2)C11—H11A0.9600
C4—C51.515 (2)C11—H11B0.9600
C4—H40.9800C11—H11C0.9600
C5—O51.2194 (19)C21—H21A0.9600
C6—C71.5363 (17)C21—H21B0.9600
C6—H6A0.9700C21—H21C0.9600
C6—H6B0.9700C22—H22A0.9600
C7—O7A1.2467 (17)C22—H22B0.9600
C7—O7B1.2472 (17)C22—H22C0.9600
C5—N1—C6120.35 (12)C9—C8—H8A108.5
C5—N1—C2114.20 (11)C4—C8—H8B108.5
C6—N1—C2124.73 (12)C9—C8—H8B108.5
N1—C2—N3100.61 (10)H8A—C8—H8B107.5
N1—C2—C22112.45 (11)C10—C9—C11110.07 (15)
N3—C2—C22109.03 (10)C10—C9—C8112.21 (14)
N1—C2—C21112.66 (11)C11—C9—C8110.02 (15)
N3—C2—C21109.70 (12)C10—C9—H9108.1
C22—C2—C21111.77 (13)C11—C9—H9108.1
C4—N3—C2107.84 (10)C8—C9—H9108.1
C4—N3—H3A110.1C9—C10—H10A109.5
C2—N3—H3A110.1C9—C10—H10B109.5
C4—N3—H3B110.1H10A—C10—H10B109.5
C2—N3—H3B110.1C9—C10—H10C109.5
H3A—N3—H3B108.5H10A—C10—H10C109.5
N3—C4—C8113.12 (11)H10B—C10—H10C109.5
N3—C4—C5102.15 (11)C9—C11—H11A109.5
C8—C4—C5113.55 (12)C9—C11—H11B109.5
N3—C4—H4109.3H11A—C11—H11B109.5
C8—C4—H4109.3C9—C11—H11C109.5
C5—C4—H4109.3H11A—C11—H11C109.5
O5—C5—N1125.63 (15)H11B—C11—H11C109.5
O5—C5—C4125.88 (14)C2—C21—H21A109.5
N1—C5—C4108.49 (12)C2—C21—H21B109.5
N1—C6—C7114.65 (10)H21A—C21—H21B109.5
N1—C6—H6A108.6C2—C21—H21C109.5
C7—C6—H6A108.6H21A—C21—H21C109.5
N1—C6—H6B108.6H21B—C21—H21C109.5
C7—C6—H6B108.6C2—C22—H22A109.5
H6A—C6—H6B107.6C2—C22—H22B109.5
O7A—C7—O7B125.68 (12)H22A—C22—H22B109.5
O7A—C7—C6118.18 (12)C2—C22—H22C109.5
O7B—C7—C6116.12 (11)H22A—C22—H22C109.5
C4—C8—C9115.07 (12)H22B—C22—H22C109.5
C4—C8—H8A108.5
C5—N1—C2—N316.44 (13)C2—N1—C5—C41.44 (15)
C6—N1—C2—N3173.30 (10)N3—C4—C5—O5166.10 (15)
C5—N1—C2—C22132.31 (13)C8—C4—C5—O544.0 (2)
C6—N1—C2—C2257.43 (15)N3—C4—C5—N114.53 (13)
C5—N1—C2—C21100.30 (15)C8—C4—C5—N1136.67 (12)
C6—N1—C2—C2169.96 (16)C5—N1—C6—C769.75 (17)
N1—C2—N3—C425.14 (11)C2—N1—C6—C799.95 (15)
C22—C2—N3—C4143.54 (11)N1—C6—C7—O7A22.0 (2)
C21—C2—N3—C493.76 (13)N1—C6—C7—O7B159.69 (14)
C2—N3—C4—C8147.13 (11)N3—C4—C8—C970.17 (15)
C2—N3—C4—C524.70 (12)C5—C4—C8—C9174.00 (12)
C6—N1—C5—O57.2 (2)C4—C8—C9—C1069.84 (18)
C2—N1—C5—O5177.93 (15)C4—C8—C9—C11167.25 (15)
C6—N1—C5—C4172.17 (11)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N3—H3A···O7Bi0.901.792.688 (2)172
N3—H3B···O7Aii0.901.802.685 (2)169
Symmetry codes: (i) x+1, y+1, z; (ii) x, y+1, z.

Experimental details

(I)(II)
Crystal data
Chemical formula3C8H16N2O3·2H2OC11H20N2O3
Mr600.72228.29
Crystal system, space groupOrthorhombic, P212121Triclinic, P1
Temperature (K)299298
a, b, c (Å)8.735 (5), 15.54 (1), 24.238 (15)6.0060 (14), 6.8782 (18), 7.9717 (18)
α, β, γ (°)90, 90, 9090.202 (11), 98.272 (8), 107.193 (11)
V3)3290 (4)310.96 (13)
Z41
Radiation typeMo KαMo Kα
µ (mm1)0.100.09
Crystal size (mm)0.49 × 0.07 × 0.020.60 × 0.55 × 0.04
Data collection
DiffractometerRigaku Mercury CCD area-detector
diffractometer
Rigaku Mercury CCD area-detector
diffractometer
Absorption correctionMulti-scan
(CrystalClear; Rigaku/MSC, 2006)
Tmin, Tmax0.661, 1.000
No. of measured, independent and
observed [I > 2σ(I)] reflections
21778, 5794, 4707 3600, 2526, 2501
Rint0.0640.013
(sin θ/λ)max1)0.5950.649
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.060, 0.161, 1.09 0.034, 0.093, 1.04
No. of reflections57942526
No. of parameters370149
No. of restraints03
H-atom treatmentH-atom parameters constrainedH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.26, 0.190.17, 0.15

Computer programs: CrystalClear (Rigaku/MSC, 2006), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), Mercury (Macrae et al., 2006), Yadokari-XG 2009 (Kabuto et al., 2009).

Selected torsion angles (º) for (I) top
N1A—C1A—C2A—N2A127.1 (3)N1B—C1B—C5B—C6B72.4 (4)
C1A—C2A—N2A—C3A173.6 (3)C2B—C1B—C5B—C6B168.4 (3)
C2A—N2A—C3A—C4A170.8 (3)C1B—C5B—C6B—C8B65.9 (5)
N2A—C3A—C4A—O2A23.5 (5)C1B—C5B—C6B—C7B171.6 (4)
N1A—C1A—C5A—C6A177.2 (3)N1C—C1C—C2C—N2C140.1 (3)
C2A—C1A—C5A—C6A58.7 (4)C1C—C2C—N2C—C3C178.4 (3)
C1A—C5A—C6A—C7A172.4 (4)C2C—N2C—C3C—C4C154.5 (3)
C1A—C5A—C6A—C8A63.8 (5)N2C—C3C—C4C—O2C14.9 (4)
N1B—C1B—C2B—N2B143.9 (3)N1C—C1C—C5C—C6C169.2 (3)
C1B—C2B—N2B—C3B176.3 (3)C2C—C1C—C5C—C6C71.1 (4)
C2B—N2B—C3B—C4B173.5 (3)C1C—C5C—C6C—C8C63.5 (5)
N2B—C3B—C4B—O2B1.9 (5)C1C—C5C—C6C—C7C172.7 (4)
Hydrogen-bond geometry (Å, º) for (I) top
D—H···AD—HH···AD···AD—H···A
N1A—H1A···O3Ai0.872.203.060 (4)172.1
N1A—H2A···O2Cii0.871.852.709 (4)168.5
N1A—H3A···O3Bi0.871.882.690 (4)153.5
N1B—H1B···O3Bi0.871.962.816 (4)167.2
N1B—H2B···O3Aiii0.872.162.953 (4)152.1
N1B—H3B···O3Ci0.871.972.768 (4)151.2
N1C—H1C···O3Ci0.872.042.838 (4)152.4
N1C—H2C···O2Aiii0.871.902.750 (4)165.5
N1C—H3C···O2Wi0.871.892.762 (5)175.8
N2C—H5C···O1W0.872.403.202 (5)153.1
O1W—H1W···O3Aiv0.822.042.857 (5)177.1
O1W—H2W···O1Biii0.822.192.933 (5)149.9
O2W—H3W···O1Av0.821.962.773 (5)176.1
O2W—H4W···O1W0.822.373.134 (5)155.5
O2W—H4W···O2C0.822.452.882 (5)114.3
C1A—H4A···O1B0.982.333.250 (4)155.9
C1B—H4B···O1C0.982.453.425 (4)170.9
C3C—H6C···O2B0.972.333.181 (5)146.0
Symmetry codes: (i) x+1, y, z; (ii) x+1, y1/2, z+1/2; (iii) x+1, y+1/2, z+1/2; (iv) x, y+1, z; (v) x1, y+1, z.
Selected torsion angles (º) for (II) top
C5—N1—C2—N316.44 (13)N3—C4—C5—N114.53 (13)
N1—C2—N3—C425.14 (11)C2—N1—C6—C799.95 (15)
C2—N3—C4—C524.70 (12)N1—C6—C7—O7A22.0 (2)
C2—N1—C5—O5177.93 (15)N3—C4—C8—C970.17 (15)
C6—N1—C5—C4172.17 (11)C4—C8—C9—C1069.84 (18)
C2—N1—C5—C41.44 (15)C4—C8—C9—C11167.25 (15)
Hydrogen-bond geometry (Å, º) for (II) top
D—H···AD—HH···AD···AD—H···A
N3—H3A···O7Bi0.901.792.688 (2)172.1
N3—H3B···O7Aii0.901.802.685 (2)169.1
Symmetry codes: (i) x+1, y+1, z; (ii) x, y+1, z.
 

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