Packing modes of (R,R)-tartaric acid esters and amides

The molecular packing modes of a series of mono- and diamides of (R,R)-tartaric acid are discussed on the basis of their crystal structures. Derivatives include combinations of methylester, amide, N-methylamide and N,N-dimethylamide groups, both symmetrically and asymmetrically substituted. The symmetrically substituted derivatives do not utilize their C₂ symmetry in the crystal. The packing of primary tartramides seems to be driven by NH...O=C hydrogen bonds and supplemented by strong OH...O=C and weak NH...OH bonds. On the other hand, in derivatives containing methylester and/or methylamide groups OH...OH...O=C hydrogen-bond patterns seem to dominate. Types of aggregates, characteristic for the investigated derivatives, include cyclic dimers and ring systems analogous to the dimers, but formed by two different although complementary functional groups, as well as sets of chains aligned in a manner resembling the helical arrangement of peptides. The helices are formed along the screw axis with an identity period of approximately 5 Å. In tartramic acids, containing in one molecule both carboxyl and amide functions, in competition between the two groups to control the molecular arrangement, the latter dominates, unless it is N-substituted tartramide, in which case the carboxyl group predominates. Problems with packing, which occur in some of the structures owing to the steric bulk of the methyl groups, are overcome by changes in conformation (esters) or by co-crystallization with solvent water molecules (methylamides and dimethylamides). These derivatives are also more likely to crystallize with multiple asymmetric units.

Computing details

For all compounds, data collection: Kuma KM-4 Software (Kuma Diffraction, 1991). Cell refinement: Kuma KM-4 Software (Kuma Diffraction, 1991) for hoh1; Kuma KM-4 Software for hn12, hn22. Data reduction: Kuma KM-4 Software (Kuma Diffraction, 1991) for hoh1; Kuma KM-4 Software for hn12, hn22. For all compounds, program(s) used to solve structure: SHELXS86 (Sheldrick, 1990); program(s) used to refine structure: SHELXL93 (Sheldrick, 1993); molecular graphics: Simens Analytical X-Ray Instruments (1989); software used to prepare material for publication: SHELXL93 (Sheldrick, 1993).

Figures

(hoh1) (R,R)-(+)-Tartaric acid monoamide

Crystal data

C4H7NO5	Dx = 1.726 Mg m^−3
Mr = 149.11	Melting point = 443–445 K
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
a = 5.9556 (5) Å	Cell parameters from 46 reflections
b = 8.0972 (5) Å	θ = 12.2–15.0°
c = 11.8960 (8) Å	µ = 0.16 mm^−1
V = 573.67 (7) Å^3	T = 293 K
Z = 4	Square pyramid, colourless
F(000) = 312	0.5 × 0.5 × 0.5 mm

Data collection

KM-4 four circle diffractometer	Rint = 0.011
Radiation source: fine-focus sealed tube	θmax = 29.1°, θmin = 3.0°
Graphite monochromator	h = −8→8
θ–2θ scans	k = 0→11
1688 measured reflections	l = 0→16
1534 independent reflections	2 standard reflections every 100 reflections
1476 reflections with I > σ(I)	intensity decay: 1.0%

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.033	Riding model
wR(F^2) = 0.099	Calculated w = 1/[σ^2(Fo^2) + (0.0485P)^2 + 0.1655P] where P = (Fo^2 + 2Fc^2)/3
S = 1.01	(Δ/σ)max = −0.054
1531 reflections	Δρmax = 0.39 e Å^−3
103 parameters	Δρmin = −0.18 e Å^−3
0 restraints	Absolute structure: Flack H D (1983), Acta Cryst. A39, 876-881
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.80 (114)

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 on F² for ALL reflections except for 3 with very negative F² or flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The observed criterion of F² > σ(F²) is used only for calculating _R_factor_obs 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 (Ų)

	x	y	z	Uiso*/Ueq
C1	0.2145 (2)	−0.5652 (2)	−0.49757 (10)	0.0206 (2)
C2	−0.0044 (2)	−0.56737 (15)	−0.43187 (9)	0.0183 (2)
H2	−0.0111 (2)	−0.66799 (15)	−0.38932 (9)	0.020*
C3	−0.0080 (2)	−0.42239 (15)	−0.34979 (10)	0.0214 (2)
H3	0.1212 (2)	−0.42979 (15)	−0.30182 (10)	0.020*
C4	−0.2183 (2)	−0.4313 (2)	−0.27706 (10)	0.0224 (2)
N4	−0.3519 (2)	−0.3024 (2)	−0.28003 (11)	0.0339 (3)
H41	−0.4785 (2)	−0.3014 (2)	−0.23877 (11)	0.060*
H42	−0.3167 (2)	−0.2149 (2)	−0.32325 (11)	0.060*
O1	0.2225 (2)	−0.56502 (14)	−0.59877 (8)	0.0302 (2)
O2	−0.19040 (13)	−0.56349 (14)	−0.50508 (8)	0.0237 (2)
H2O	−0.161 (5)	−0.516 (3)	−0.566 (2)	0.055 (7)*
O3	0.0052 (2)	−0.27569 (13)	−0.41215 (10)	0.0349 (3)
H3O	0.071 (4)	−0.211 (3)	−0.375 (2)	0.044 (6)*
O4	−0.2518 (2)	−0.55460 (13)	−0.21725 (8)	0.0297 (2)
O10	0.3878 (2)	−0.56387 (15)	−0.42987 (8)	0.0295 (2)
H10	0.506 (4)	−0.552 (3)	−0.4650 (18)	0.040 (5)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0167 (5)	0.0224 (5)	0.0229 (5)	0.0000 (4)	0.0018 (4)	−0.0006 (5)
C2	0.0150 (4)	0.0225 (5)	0.0176 (5)	0.0004 (5)	0.0005 (4)	−0.0006 (4)
C3	0.0200 (5)	0.0235 (5)	0.0207 (5)	−0.0011 (5)	−0.0003 (4)	−0.0034 (4)
C4	0.0210 (5)	0.0278 (5)	0.0184 (5)	0.0005 (5)	−0.0010 (4)	−0.0061 (4)
N4	0.0303 (6)	0.0334 (6)	0.0380 (6)	0.0087 (5)	0.0044 (5)	−0.0039 (5)
O1	0.0244 (4)	0.0455 (5)	0.0208 (4)	0.0011 (5)	0.0038 (3)	0.0006 (4)
O2	0.0155 (4)	0.0360 (5)	0.0197 (4)	−0.0008 (4)	−0.0013 (3)	−0.0002 (4)
O3	0.0433 (6)	0.0236 (4)	0.0378 (6)	−0.0077 (5)	0.0044 (5)	0.0020 (4)
O4	0.0304 (5)	0.0336 (5)	0.0250 (4)	0.0015 (4)	0.0062 (4)	0.0028 (4)
O10	0.0157 (4)	0.0475 (6)	0.0253 (4)	−0.0015 (4)	−0.0001 (3)	−0.0011 (4)

Geometric parameters (Å, º)

C1—O1	1.205 (2)	C3—H3	0.96
C1—O10	1.3089 (15)	C4—O4	1.242 (2)
C1—C2	1.520 (2)	C4—N4	1.313 (2)
C2—O2	1.4093 (13)	N4—H41	0.90
C2—C3	1.527 (2)	N4—H42	0.90
C2—H2	0.96	O2—H2O	0.84 (3)
C3—O3	1.403 (2)	O3—H3O	0.79 (3)
C3—C4	1.524 (2)	O10—H10	0.83 (2)
O1—C1—O10	125.70 (11)	O3—C3—H3	108.80 (7)
O1—C1—C2	123.20 (10)	C4—C3—H3	108.57 (6)
O10—C1—C2	111.10 (10)	C2—C3—H3	108.72 (7)
O2—C2—C1	110.86 (9)	O4—C4—N4	123.84 (12)
O2—C2—C3	111.54 (10)	O4—C4—C3	119.69 (11)
C1—C2—C3	109.38 (10)	N4—C4—C3	116.44 (12)
O2—C2—H2	108.19 (7)	C4—N4—H41	120.02 (8)
C1—C2—H2	108.43 (6)	C4—N4—H42	119.98 (8)
C3—C2—H2	108.34 (6)	H41—N4—H42	120.0
O3—C3—C4	112.73 (11)	C2—O2—H2O	112.2 (18)
O3—C3—C2	108.18 (10)	C3—O3—H3O	107.0 (17)
C4—C3—C2	109.76 (10)	C1—O10—H10	111.3 (15)

(hn12) (R,R)-(+)-Tartaric acid N-methyldiamide

Crystal data

C5H10N2O4	Melting point = 475–477 K
Mr = 162.15	Mo Kα radiation, λ = 0.71073 Å
Tetragonal, P41212	Cell parameters from 47 reflections
a = 10.594 (1) Å	θ = 6.1–12.0°
c = 13.771 (3) Å	µ = 0.12 mm^−1
V = 1545.6 (4) Å^3	T = 293 K
Z = 8	Tetragonal bipyramid, colourless
F(000) = 688	0.45 × 0.44 × 0.41 mm
Dx = 1.394 Mg m^−3

Data collection

KM-4 four circle diffractometer	Rint = 0.013
Radiation source: fine-focus sealed tube	θmax = 27.1°, θmin = 2.4°
Graphite monochromator	h = 0→13
Θ–2Θ scans	k = 0→13
1939 measured reflections	l = 0→17
1698 independent reflections	2 standard reflections every 100 reflections
1408 reflections with I > 2σ(I)	intensity decay: 0.9%

Refinement

Refinement on F^2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	Riding model
R[F^2 > 2σ(F^2)] = 0.042	Calculated w = 1/[σ^2(Fo^2) + (0.0699P)^2 + 0.2727P] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.122	(Δ/σ)max < 0.001
S = 1.10	Δρmax = 0.28 e Å^−3
1698 reflections	Δρmin = −0.23 e Å^−3
113 parameters	Extinction correction: SHELXL, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
0 restraints	Extinction coefficient: 0.0304 (45)
Primary atom site location: structure-invariant direct methods	Absolute structure: Flack H D (1983), Acta Cryst. A39, 876-881
Secondary atom site location: difference Fourier map	Absolute structure parameter: 0.72 (187)

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 on F² for ALL reflections except for 0 with very negative F² or flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The observed criterion of F² > σ(F²) is used only for calculating _R_factor_obs 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 (Ų)

	x	y	z	Uiso*/Ueq	Occ. (<1)
C1	1.0031 (2)	0.3259 (2)	−0.19146 (15)	0.0333 (5)
C2	0.9944 (2)	0.2357 (2)	−0.10640 (14)	0.0318 (5)
H2	1.0751 (2)	0.2327 (2)	−0.07477 (14)	0.038*
C3	0.8969 (2)	0.2848 (2)	−0.03486 (14)	0.0337 (5)
H3	0.9222 (2)	0.3666 (2)	−0.01209 (14)	0.040*
C4	0.8908 (2)	0.1938 (2)	0.0499 (2)	0.0389 (5)
C41	0.7692 (4)	0.0247 (6)	0.1287 (4)	0.0533 (13)	0.60
H411	0.8349 (4)	0.0231 (6)	0.1767 (4)	0.064*	0.60
H412	0.7710 (4)	−0.0524 (6)	0.0921 (4)	0.064*	0.60
H413	0.6887 (4)	0.0304 (6)	0.1603 (4)	0.064*	0.60
C42	0.7585 (16)	0.0782 (17)	0.1626 (12)	0.120 (6)*	0.40
N1	0.9727 (2)	0.2826 (2)	−0.27842 (13)	0.0412 (5)
H12	0.9602 (2)	0.1986 (2)	−0.28028 (13)	0.049*
H11	0.9779 (2)	0.3378 (2)	−0.32794 (13)	0.049*
N4	0.7865 (2)	0.1311 (3)	0.0609 (2)	0.0710 (9)
H4	0.7223 (2)	0.1474 (3)	0.0199 (2)	0.085*
O1	1.0369 (2)	0.4354 (2)	−0.17790 (12)	0.0452 (5)
O2	0.9608 (2)	0.1130 (2)	−0.13644 (12)	0.0396 (4)
H2O	1.020 (3)	0.074 (3)	−0.131 (2)	0.058 (10)*
O3	0.77673 (15)	0.2933 (2)	−0.07847 (13)	0.0444 (4)
H3O	0.772 (3)	0.364 (4)	−0.090 (2)	0.062 (10)*
O4	0.98510 (15)	0.1790 (2)	0.10183 (11)	0.0423 (4)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0285 (10)	0.0376 (11)	0.0338 (10)	−0.0005 (8)	−0.0039 (8)	0.0031 (8)
C2	0.0295 (10)	0.0339 (10)	0.0320 (9)	−0.0014 (8)	−0.0042 (8)	0.0020 (8)
C3	0.0288 (10)	0.0361 (11)	0.0360 (10)	0.0007 (8)	−0.0035 (8)	0.0027 (9)
C4	0.0318 (11)	0.0479 (13)	0.0370 (11)	0.0002 (10)	−0.0005 (9)	0.0059 (9)
C41	0.041 (2)	0.066 (3)	0.053 (2)	−0.020 (2)	−0.004 (2)	0.036 (2)
N1	0.0521 (12)	0.0393 (10)	0.0324 (8)	−0.0034 (9)	−0.0060 (8)	0.0049 (8)
N4	0.0388 (11)	0.107 (2)	0.0672 (15)	−0.0159 (13)	−0.0100 (11)	0.052 (2)
O1	0.0595 (11)	0.0375 (9)	0.0387 (9)	−0.0131 (7)	−0.0137 (8)	0.0047 (7)
O2	0.0406 (9)	0.0328 (8)	0.0454 (9)	0.0004 (7)	−0.0083 (7)	0.0007 (7)
O3	0.0289 (8)	0.0477 (10)	0.0567 (10)	0.0031 (7)	−0.0057 (7)	0.0177 (8)
O4	0.0380 (9)	0.0497 (10)	0.0394 (8)	−0.0024 (7)	−0.0102 (7)	0.0085 (7)

Geometric parameters (Å, º)

C1—O1	1.228 (3)	C41—N4	1.476 (4)
C1—N1	1.322 (3)	C41—H411	0.96
C1—C2	1.514 (3)	C41—H412	0.96
C2—O2	1.410 (2)	C41—H413	0.96
C2—C3	1.519 (3)	C42—N4	1.54 (2)
C2—H2	0.96	N1—H12	0.90
C3—O3	1.410 (3)	N1—H11	0.90
C3—C4	1.515 (3)	N4—H4	0.90
C3—H3	0.96	O2—H2O	0.76 (3)
C4—O4	1.238 (3)	O3—H3O	0.76 (4)
C4—N4	1.298 (3)
O1—C1—N1	122.4 (2)	N4—C41—H411	111.0 (2)
O1—C1—C2	119.7 (2)	N4—C41—H412	108.4 (3)
N1—C1—C2	117.8 (2)	H411—C41—H412	109.5
O2—C2—C1	111.7 (2)	N4—C41—H413	110.4 (2)
O2—C2—C3	109.5 (2)	H411—C41—H413	109.5
C1—C2—C3	109.1 (2)	H412—C41—H413	108.1
O2—C2—H2	109.07 (11)	C1—N1—H12	113.87 (13)
C1—C2—H2	108.53 (11)	C1—N1—H11	116.47 (13)
C3—C2—H2	108.83 (10)	H12—N1—H11	129.0
O3—C3—C4	109.3 (2)	C4—N4—C41	124.8 (3)
O3—C3—C2	111.1 (2)	C4—N4—C42	117.2 (7)
C4—C3—C2	108.1 (2)	C41—N4—C42	28.5 (6)
O3—C3—H3	109.50 (12)	C4—N4—H4	118.18 (14)
C4—C3—H3	109.54 (12)	C41—N4—H4	116.7 (2)
C2—C3—H3	109.30 (11)	C42—N4—H4	119.7 (6)
O4—C4—N4	123.7 (2)	C2—O2—H2O	106 (2)
O4—C4—C3	119.4 (2)	C3—O3—H3O	102 (3)
N4—C4—C3	116.8 (2)
O1—C1—C2—O2	−176.8 (2)	O3—C3—C4—O4	−175.5 (2)
N1—C1—C2—O2	3.6 (3)	C2—C3—C4—O4	63.5 (3)
O1—C1—C2—C3	62.0 (3)	O3—C3—C4—N4	7.4 (3)
N1—C1—C2—C3	−117.6 (2)	C2—C3—C4—N4	−113.6 (3)
O2—C2—C3—O3	−61.9 (2)	O4—C4—N4—C41	−7.0 (6)
C1—C2—C3—O3	60.7 (2)	C3—C4—N4—C41	169.9 (4)
O2—C2—C3—C4	58.0 (2)	O4—C4—N4—C42	25.1 (8)
C1—C2—C3—C4	−179.4 (2)	C3—C4—N4—C42	−158.0 (7)

(hn22) (R,R)-(+)-Tartaric acid N,N'-dimethyldiamide monohydrate

Crystal data

C6H14N2O5	Dx = 1.382 Mg m^−3
Mr = 194.19	Melting point = 471–473 K
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
a = 5.094 (1) Å	Cell parameters from 40 reflections
b = 11.243 (2) Å	θ = 5.9–19.1°
c = 16.295 (4) Å	µ = 0.12 mm^−1
V = 933.2 (3) Å^3	T = 293 K
Z = 4	Needle, colourless
F(000) = 416	0.3 × 0.3 × 0.2 mm

Data collection

KM-4 four circle diffractometer	Rint = 0.103
Radiation source: fine-focus sealed tube	θmax = 27.1°, θmin = 2.2°
Graphite monochromator	h = −6→6
Θ–2Θ scans	k = 0→14
2216 measured reflections	l = 0→20
2058 independent reflections	3 standard reflections every 100 reflections
1696 reflections with I > 2σ(I)	intensity decay: 0.5%

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.057	Riding model
wR(F^2) = 0.163	Calculated w = 1/[σ^2(Fo^2) + (0.1129P)^2 + 0.4981P] where P = (Fo^2 + 2Fc^2)/3
S = 1.04	(Δ/σ)max < 0.001
2057 reflections	Δρmax = 0.28 e Å^−3
134 parameters	Δρmin = −0.26 e Å^−3
0 restraints	Absolute structure: Flack H D (1983), Acta Cryst. A39, 876-881
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: −1.63 (188)

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 on F² for ALL reflections except for 1 with very negative F² or flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The observed criterion of F² > σ(F²) is used only for calculating _R_factor_obs 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 (Ų)

	x	y	z	Uiso*/Ueq
C1	0.1536 (6)	0.0027 (2)	0.5434 (2)	0.0137 (6)
C2	0.2217 (6)	0.0950 (2)	0.4793 (2)	0.0110 (6)
H2	0.4085 (6)	0.0966 (2)	0.4716 (2)	0.010*
C3	0.0882 (5)	0.0638 (2)	0.3981 (2)	0.0121 (5)
H3	0.1671 (5)	−0.0064 (2)	0.3753 (2)	0.010*
C4	0.1282 (6)	0.1690 (2)	0.3392 (2)	0.0121 (5)
C11	−0.0636 (8)	−0.0391 (3)	0.6732 (2)	0.0267 (7)
H111	−0.0817 (8)	0.0068 (3)	0.7226 (2)	0.040*
H112	0.0621 (8)	−0.1016 (3)	0.6812 (2)	0.040*
H113	−0.2289 (8)	−0.0742 (3)	0.6586 (2)	0.040*
C41	−0.0827 (6)	0.3090 (2)	0.2470 (2)	0.0183 (6)
H411	−0.2443 (6)	0.3146 (2)	0.2170 (2)	0.030*
H412	0.0603 (6)	0.2981 (2)	0.2094 (2)	0.030*
H413	−0.0532 (6)	0.3817 (2)	0.2765 (2)	0.030*
O1	0.2172 (5)	−0.1028 (2)	0.53222 (14)	0.0200 (5)
O2	0.1340 (4)	0.2092 (2)	0.50499 (12)	0.0124 (4)
H2O	0.306 (10)	0.248 (4)	0.511 (3)	0.034 (11)*
O3	−0.1830 (4)	0.0447 (2)	0.40978 (13)	0.0153 (5)
H3O	−0.221 (8)	−0.029 (4)	0.407 (2)	0.023 (10)*
O4	0.3488 (4)	0.2097 (2)	0.32678 (13)	0.0149 (4)
N1	0.0234 (5)	0.0406 (2)	0.6085 (2)	0.0171 (5)
H1	−0.0119 (5)	0.1187 (2)	0.6131 (2)	0.040*
N4	−0.0892 (5)	0.2101 (2)	0.30444 (14)	0.0135 (5)
H4	−0.2441 (5)	0.1759 (2)	0.31662 (14)	0.010*
O1W	−0.4143 (5)	−0.1676 (2)	0.4156 (2)	0.0192 (5)
H1W	−0.334 (11)	−0.228 (6)	0.424 (4)	0.059 (17)*
H2W	−0.527 (12)	−0.152 (4)	0.441 (3)	0.037 (14)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0148 (13)	0.0104 (11)	0.0161 (13)	0.0008 (10)	−0.0022 (10)	0.0022 (10)
C2	0.0134 (12)	0.0053 (12)	0.0145 (13)	0.0011 (9)	0.0019 (10)	−0.0008 (10)
C3	0.0130 (13)	0.0087 (11)	0.0145 (13)	0.0004 (9)	0.0007 (11)	−0.0006 (9)
C4	0.0161 (13)	0.0091 (11)	0.0112 (13)	0.0007 (10)	0.0000 (10)	−0.0024 (9)
C11	0.044 (2)	0.0156 (14)	0.021 (2)	0.0026 (14)	0.0097 (14)	0.0073 (12)
C41	0.0198 (14)	0.0155 (13)	0.0196 (14)	−0.0001 (11)	−0.0021 (12)	0.0068 (11)
O1	0.0271 (12)	0.0084 (9)	0.0246 (11)	0.0038 (8)	0.0053 (9)	0.0024 (8)
O2	0.0149 (9)	0.0054 (8)	0.0170 (10)	0.0000 (8)	0.0006 (8)	−0.0023 (7)
O3	0.0140 (10)	0.0081 (9)	0.0238 (11)	−0.0023 (8)	0.0001 (8)	0.0020 (8)
O4	0.0147 (10)	0.0137 (9)	0.0163 (10)	−0.0013 (8)	0.0013 (8)	0.0006 (7)
N1	0.0267 (13)	0.0082 (10)	0.0165 (13)	0.0004 (10)	0.0035 (10)	0.0029 (9)
N4	0.0126 (11)	0.0129 (10)	0.0148 (11)	−0.0007 (9)	0.0003 (9)	0.0041 (9)
O1W	0.0212 (12)	0.0092 (9)	0.0272 (13)	0.0015 (8)	0.0048 (10)	0.0011 (8)

Geometric parameters (Å, º)

C1—O1	1.243 (3)	C11—H112	0.96
C1—N1	1.321 (4)	C11—H113	0.96
C1—C2	1.512 (4)	C41—N4	1.453 (3)
C2—O2	1.422 (3)	C41—H411	0.96
C2—C3	1.529 (4)	C41—H412	0.96
C2—H2	0.96	C41—H413	0.96
C3—O3	1.411 (3)	O2—H2O	0.98 (5)
C3—C4	1.537 (3)	O3—H3O	0.85 (5)
C3—H3	0.96	N1—H1	0.90
C4—O4	1.230 (4)	N4—H4	0.90
C4—N4	1.327 (4)	O1W—H1W	0.81 (6)
C11—N1	1.453 (4)	O1W—H2W	0.73 (6)
C11—H111	0.96
O1—C1—N1	123.8 (3)	H111—C11—H112	110.2
O1—C1—C2	119.6 (3)	N1—C11—H113	110.0 (2)
N1—C1—C2	116.6 (2)	H111—C11—H113	110.2
O2—C2—C1	110.1 (2)	H112—C11—H113	108.5
O2—C2—C3	108.8 (2)	N4—C41—H411	111.1 (2)
C1—C2—C3	109.7 (2)	N4—C41—H412	109.3 (2)
O2—C2—H2	109.46 (14)	H411—C41—H412	109.4
C1—C2—H2	109.3 (2)	N4—C41—H413	109.4 (2)
C3—C2—H2	109.38 (15)	H411—C41—H413	109.4
O3—C3—C2	110.7 (2)	H412—C41—H413	108.0
O3—C3—C4	109.4 (2)	C2—O2—H2O	99 (3)
C2—C3—C4	107.7 (2)	C3—O3—H3O	111 (3)
O3—C3—H3	109.72 (14)	C1—N1—C11	122.5 (2)
C2—C3—H3	109.71 (14)	C1—N1—H1	118.79 (15)
C4—C3—H3	109.59 (14)	C11—N1—H1	118.7 (2)
O4—C4—N4	124.3 (2)	C4—N4—C41	121.5 (2)
O4—C4—C3	120.7 (3)	C4—N4—H4	119.25 (15)
N4—C4—C3	115.1 (2)	C41—N4—H4	119.3 (2)
N1—C11—H111	107.8 (2)	H1W—O1W—H2W	120 (6)
N1—C11—H112	110.3 (2)
O1—C1—C2—O2	−179.3 (3)	O3—C3—C4—O4	172.3 (2)
N1—C1—C2—O2	1.8 (4)	C2—C3—C4—O4	51.9 (3)
O1—C1—C2—C3	61.0 (4)	O3—C3—C4—N4	−7.6 (3)
N1—C1—C2—C3	−117.9 (3)	C2—C3—C4—N4	−128.0 (2)
O2—C2—C3—O3	−68.5 (3)	O1—C1—N1—C11	−1.3 (5)
C1—C2—C3—O3	52.0 (3)	C2—C1—N1—C11	177.6 (3)
O2—C2—C3—C4	51.0 (3)	O4—C4—N4—C41	0.3 (4)
C1—C2—C3—C4	171.6 (2)	C3—C4—N4—C41	−179.7 (2)