Diastereomeric salts of lactic acid and 1-phenyl­ethylamine, their structures and relative stabilities

Crystal structures have been determined for the two diastereomeric salts formed between S-lactic acid (S-LA) and 1-phenylethylamine (PEA). The relative stabilities of the salts have been investigated by differential scanning calorimetry and solubility measurements in acetonitrile. The less soluble salt obtained from water, (R-PEA)(S-LA), is the less dense. It belongs to the orthorhombic space group , . The more soluble salt, (S-PEA)(S-LA)·HO, crystallized from ethanol is monoclinic, space group , . The crystal structure showed that the water molecule is well integrated into the hydrogen-bond network in the more soluble salt, which explains the fruitless attempts made to obtain the corresponding unhydrated salt. The lactate ion adopts different conformations in the two salts. The relative energies were investigated by Hartree-Fock calculations, showing that the lactate ion is in a conformation with higher energy in the more soluble salt. The difference in solubility between the two salts can be attributed to an interplay of enthalpy and entropy effects.

Computing details

For both compounds, data collection: CAD-4 (Enraf-Nonius, 1989); cell refinement: CAD-4 (Enraf-Nonius, 1989); data reduction: DREADD (Blessing, 1987); program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPII (Johnson, 1976).

Figures

(R) R-1-Phenylethylammonium S-Lactate

Crystal data

C8H12N^+·C3H5O3^−	Dx = 1.213 Mg m^−3
Mr = 211.26	Melting point: 398.9(6) K
Orthorhombic, P212121	Cu Kα radiation, λ = 1.54180 Å
Hall symbol: P 2ac 2ab	Cell parameters from 25 reflections
a = 6.8465 (10) Å	θ = 39.9–42.2°
b = 6.9702 (7) Å	µ = 0.72 mm^−1
c = 24.248 (4) Å	T = 122 K
V = 1157.1 (3) Å^3	Plate, colourless
Z = 4	0.48 × 0.21 × 0.12 mm
F(000) = 456

Data collection

Enraf-Nonius CAD-4 diffractometer	Rint = 0.021
Radiation source: fine-focus sealed tube	θmax = 74.9°, θmin = 3.7°
Graphite monochromator	h = 0→8
ω –2θ scans	k = 0→8
8032 measured reflections	l = −29→30
2384 independent reflections	5 standard reflections every 167 min
2342 reflections with I > 2σ(I)	intensity decay: 9.2%

Refinement

Refinement on F^2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	All H-atom parameters refined
R[F^2 > 2σ(F^2)] = 0.028	w = 1/[σ^2(Fo^2) + (0.057P)^2 + 0.081P] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.077	(Δ/σ)max < 0.001
S = 1.03	Δρmax = 0.24 e Å^−3
2384 reflections	Δρmin = −0.21 e Å^−3
205 parameters	Extinction correction: SHELXL, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
0 restraints	Extinction coefficient: 0.0116 (10)
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: 0.03 (14)

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 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 (Ų)

	x	y	z	Uiso*/Ueq
O1	0.87450 (11)	0.18329 (11)	0.19946 (3)	0.02627 (18)
O2	0.68966 (12)	−0.07601 (11)	0.21312 (3)	0.0304 (2)
O3	0.54364 (11)	0.40455 (10)	0.19709 (3)	0.02632 (18)
C1	0.71393 (14)	0.09831 (14)	0.19988 (4)	0.0200 (2)
C2	0.53014 (14)	0.20717 (14)	0.18255 (4)	0.0205 (2)
C3	0.50514 (17)	0.1914 (2)	0.12039 (4)	0.0297 (2)
H2O	0.482 (2)	0.417 (2)	0.2290 (5)	0.031 (3)*
H2C	0.417 (2)	0.143 (2)	0.2012 (6)	0.027 (3)*
H3A	0.385 (3)	0.255 (3)	0.1103 (8)	0.054 (5)*
H3B	0.618 (3)	0.253 (2)	0.1015 (7)	0.044 (5)*
H3C	0.497 (3)	0.067 (3)	0.1077 (7)	0.057 (5)*
N	0.92057 (12)	0.60007 (12)	0.20306 (3)	0.02020 (18)
C4	1.19783 (17)	0.75942 (18)	0.15650 (5)	0.0303 (2)
C5	1.06116 (14)	0.58710 (15)	0.15571 (4)	0.0221 (2)
C6	0.94885 (15)	0.56932 (16)	0.10202 (4)	0.0228 (2)
C7	0.82354 (18)	0.71305 (18)	0.08416 (5)	0.0323 (2)
C8	0.72198 (19)	0.6945 (2)	0.03462 (5)	0.0369 (3)
C9	0.74628 (18)	0.53228 (19)	0.00240 (4)	0.0322 (3)
C10	0.87162 (17)	0.38840 (17)	0.01950 (4)	0.0301 (2)
C11	0.97163 (15)	0.40703 (17)	0.06930 (4)	0.0262 (2)
H12A	0.982 (2)	0.607 (2)	0.2356 (5)	0.029 (3)*
H12B	0.841 (2)	0.502 (2)	0.2017 (6)	0.027 (3)*
H12C	0.843 (2)	0.725 (2)	0.2029 (7)	0.037 (4)*
H4A	1.277 (2)	0.769 (2)	0.1917 (7)	0.040 (4)*
H4B	1.123 (2)	0.880 (2)	0.1540 (6)	0.035 (4)*
H4C	1.285 (3)	0.743 (2)	0.1246 (8)	0.046 (5)*
H5	1.142 (2)	0.473 (2)	0.1604 (5)	0.025 (3)*
H7	0.815 (3)	0.823 (3)	0.1074 (7)	0.047 (4)*
H8	0.628 (3)	0.797 (3)	0.0243 (7)	0.047 (4)*
H9	0.679 (2)	0.519 (2)	−0.0337 (7)	0.037 (4)*
H10	0.888 (3)	0.280 (3)	−0.0038 (7)	0.047 (4)*
H11	1.060 (2)	0.306 (2)	0.0825 (6)	0.040 (4)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0251 (4)	0.0255 (4)	0.0282 (4)	−0.0022 (3)	−0.0060 (3)	0.0044 (3)
O2	0.0350 (4)	0.0177 (3)	0.0385 (4)	0.0028 (3)	0.0098 (3)	0.0048 (3)
O3	0.0296 (4)	0.0166 (3)	0.0328 (4)	0.0004 (3)	0.0037 (3)	−0.0020 (3)
C1	0.0271 (5)	0.0185 (4)	0.0144 (4)	−0.0006 (4)	0.0017 (3)	−0.0004 (4)
C2	0.0225 (5)	0.0170 (4)	0.0220 (4)	−0.0014 (4)	0.0017 (3)	−0.0016 (3)
C3	0.0260 (5)	0.0393 (6)	0.0239 (5)	0.0029 (5)	−0.0039 (4)	−0.0032 (4)
N	0.0230 (4)	0.0183 (4)	0.0192 (4)	−0.0023 (3)	−0.0024 (3)	−0.0005 (3)
C4	0.0271 (5)	0.0340 (6)	0.0297 (5)	−0.0084 (4)	−0.0014 (4)	0.0014 (4)
C5	0.0214 (4)	0.0228 (4)	0.0221 (4)	0.0009 (4)	−0.0013 (4)	−0.0013 (4)
C6	0.0214 (4)	0.0270 (5)	0.0198 (4)	0.0007 (4)	0.0010 (3)	−0.0007 (4)
C7	0.0367 (6)	0.0346 (5)	0.0255 (5)	0.0114 (5)	−0.0036 (5)	−0.0043 (5)
C8	0.0372 (6)	0.0454 (7)	0.0281 (5)	0.0130 (6)	−0.0059 (5)	0.0013 (5)
C9	0.0314 (5)	0.0453 (7)	0.0199 (5)	−0.0037 (5)	−0.0019 (4)	0.0004 (4)
C10	0.0344 (6)	0.0328 (5)	0.0230 (5)	−0.0036 (5)	0.0020 (4)	−0.0044 (4)
C11	0.0265 (5)	0.0274 (5)	0.0247 (5)	0.0011 (4)	0.0007 (4)	−0.0023 (4)

Geometric parameters (Å, º)

O1—C1	1.2488 (13)	C4—H4B	0.985 (17)
O2—C1	1.2677 (12)	C4—H4C	0.984 (19)
O3—C2	1.4233 (12)	C5—C6	1.5171 (13)
O3—H2O	0.887 (15)	C5—H5	0.973 (15)
C1—C2	1.5283 (14)	C6—C7	1.3883 (16)
C2—C3	1.5207 (14)	C6—C11	1.3904 (15)
C2—H2C	1.003 (14)	C7—C8	1.3939 (16)
C3—H3A	0.97 (2)	C7—H7	0.950 (18)
C3—H3B	0.996 (18)	C8—C9	1.3845 (18)
C3—H3C	0.92 (2)	C8—H8	0.991 (19)
N—C5	1.5009 (12)	C9—C10	1.3834 (17)
N—H12A	0.898 (14)	C9—H9	0.993 (17)
N—H12B	0.876 (16)	C10—C11	1.3944 (15)
N—H12C	1.019 (17)	C10—H10	0.951 (19)
C4—C5	1.5227 (15)	C11—H11	0.983 (17)
C4—H4A	1.013 (17)
C2—O3—H2O	106.3 (10)	H4A—C4—H4C	110.2 (13)
O1—C1—O2	124.90 (10)	H4B—C4—H4C	111.5 (13)
O1—C1—C2	119.15 (9)	N—C5—C6	109.65 (8)
O2—C1—C2	115.95 (9)	N—C5—C4	109.70 (8)
O3—C2—C3	108.82 (9)	C6—C5—C4	112.75 (8)
O3—C2—C1	111.00 (8)	N—C5—H5	108.9 (8)
C3—C2—C1	109.24 (8)	C6—C5—H5	108.8 (8)
O3—C2—H2C	111.8 (8)	C4—C5—H5	107.0 (8)
C3—C2—H2C	109.1 (8)	C7—C6—C11	118.58 (9)
C1—C2—H2C	106.9 (8)	C7—C6—C5	121.46 (9)
C2—C3—H3A	108.2 (12)	C11—C6—C5	119.95 (9)
C2—C3—H3B	109.7 (10)	C6—C7—C8	120.68 (11)
H3A—C3—H3B	110.2 (14)	C6—C7—H7	115.8 (11)
C2—C3—H3C	113.9 (12)	C8—C7—H7	123.5 (11)
H3A—C3—H3C	107.4 (18)	C9—C8—C7	120.13 (11)
H3B—C3—H3C	107.3 (16)	C9—C8—H8	121.6 (10)
C5—N—H12A	111.9 (10)	C7—C8—H8	118.2 (10)
C5—N—H12B	108.9 (10)	C10—C9—C8	119.84 (10)
H12A—N—H12B	111.5 (13)	C10—C9—H9	119.1 (9)
C5—N—H12C	112.6 (9)	C8—C9—H9	121.0 (9)
H12A—N—H12C	101.9 (13)	C9—C10—C11	119.77 (11)
H12B—N—H12C	109.8 (13)	C9—C10—H10	118.1 (11)
C5—C4—H4A	113.0 (9)	C11—C10—H10	122.1 (11)
C5—C4—H4B	110.7 (9)	C6—C11—C10	120.99 (10)
H4A—C4—H4B	105.9 (12)	C6—C11—H11	117.9 (9)
C5—C4—H4C	105.8 (10)	C10—C11—H11	121.1 (9)
O1—C1—C2—O3	−32.44 (12)	C11—C6—C7—C8	0.33 (18)
O2—C1—C2—O3	148.46 (8)	C5—C6—C7—C8	179.80 (11)
O1—C1—C2—C3	87.55 (11)	C6—C7—C8—C9	−0.4 (2)
O2—C1—C2—C3	−91.55 (11)	C7—C8—C9—C10	0.03 (19)
N—C5—C6—C7	62.03 (13)	C8—C9—C10—C11	0.49 (18)
C4—C5—C6—C7	−60.50 (13)	C7—C6—C11—C10	0.19 (16)
N—C5—C6—C11	−118.51 (10)	C5—C6—C11—C10	−179.29 (9)
C4—C5—C6—C11	118.96 (11)	C9—C10—C11—C6	−0.60 (17)

(S) S-1-Phenylethylammonium S-Lactate Monohydrate

Crystal data

C8H12N^+·C3H5O3^−·H2O	F(000) = 248
Mr = 229.27	Dx = 1.251 Mg m^−3
Monoclinic, P21	Melting point: 346.6(4) K
Hall symbol: P 2yb	Cu Kα radiation, λ = 1.54180 Å
a = 8.0795 (18) Å	Cell parameters from 25 reflections
b = 5.8794 (9) Å	θ = 39.5–42.2°
c = 12.852 (2) Å	µ = 0.79 mm^−1
β = 94.53 (2)°	T = 122 K
V = 608.6 (2) Å^3	Plate, colourless
Z = 2	0.50 × 0.25 × 0.16 mm

Data collection

Enraf-Nonius CAD-4 diffractometer	Rint = 0.029
Radiation source: fine-focus sealed tube	θmax = 74.8°, θmin = 3.5°
Graphite monochromator	h = −10→10
ω –2θ scans	k = −7→7
5053 measured reflections	l = 0→16
2505 independent reflections	5 standard reflections every 167 min
2503 reflections with I > 2σ(I)	intensity decay: 2.3%

Refinement

Refinement on F^2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	All H-atom parameters refined
R[F^2 > 2σ(F^2)] = 0.027	w = 1/[σ^2(Fo^2) + (0.0614P)^2 + 0.0408P] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.073	(Δ/σ)max = 0.001
S = 0.97	Δρmax = 0.30 e Å^−3
2505 reflections	Δρmin = −0.22 e Å^−3
222 parameters	Extinction correction: SHELXL, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
1 restraint	Extinction coefficient: 0.169 (6)
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: −0.02 (10)

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 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 (Ų)

	x	y	z	Uiso*/Ueq
O1	0.76329 (8)	0.71619 (12)	0.97351 (6)	0.01881 (18)
O2	0.56653 (8)	0.56118 (12)	0.86435 (6)	0.01887 (18)
O3	0.66876 (10)	1.13227 (12)	0.93262 (6)	0.02168 (19)
C1	0.63885 (12)	0.72913 (16)	0.90723 (7)	0.0145 (2)
C2	0.57329 (11)	0.96618 (16)	0.87586 (7)	0.0161 (2)
C3	0.57819 (14)	0.9988 (2)	0.75794 (8)	0.0244 (2)
H2O	0.633 (2)	1.261 (3)	0.9070 (13)	0.032 (4)*
H2C	0.4584 (15)	0.974 (2)	0.8940 (10)	0.015 (3)*
H3A	0.689 (2)	0.972 (3)	0.7371 (13)	0.033 (4)*
H3B	0.5405 (18)	1.150 (3)	0.7395 (12)	0.026 (4)*
H3C	0.502 (2)	0.889 (4)	0.7183 (14)	0.040 (4)*
N	0.22511 (10)	0.52580 (16)	0.85703 (6)	0.01653 (19)
C4	−0.03702 (12)	0.38837 (19)	0.76866 (8)	0.0217 (2)
C5	0.14668 (11)	0.42827 (17)	0.75715 (7)	0.0166 (2)
C6	0.18112 (11)	0.58341 (17)	0.66711 (7)	0.0166 (2)
C7	0.10041 (13)	0.79269 (19)	0.65234 (8)	0.0214 (2)
C8	0.13396 (14)	0.9328 (2)	0.56926 (8)	0.0252 (2)
C9	0.25039 (14)	0.8676 (2)	0.50089 (8)	0.0260 (2)
C10	0.33087 (14)	0.6602 (2)	0.51472 (8)	0.0269 (3)
C11	0.29657 (13)	0.5188 (2)	0.59761 (7)	0.0222 (2)
H12A	0.3331 (19)	0.550 (3)	0.8511 (12)	0.024 (3)*
H12B	0.2265 (18)	0.436 (3)	0.9130 (13)	0.027 (3)*
H12C	0.1742 (18)	0.652 (3)	0.8719 (11)	0.024 (4)*
H4A	−0.0943 (19)	0.530 (3)	0.7786 (12)	0.028 (4)*
H4B	−0.0490 (18)	0.299 (3)	0.8254 (13)	0.029 (4)*
H4C	−0.095 (2)	0.317 (3)	0.7075 (14)	0.034 (4)*
H5	0.1953 (16)	0.279 (3)	0.7459 (10)	0.016 (3)*
H7	0.017 (2)	0.839 (3)	0.7006 (14)	0.034 (4)*
H8	0.080 (2)	1.070 (4)	0.5608 (13)	0.034 (4)*
H9	0.2684 (19)	0.962 (4)	0.4413 (14)	0.038 (4)*
H10	0.409 (2)	0.616 (3)	0.4700 (14)	0.034 (4)*
H11	0.357 (2)	0.372 (4)	0.6057 (14)	0.041 (4)*
O1AQ	0.94302 (9)	0.41230 (14)	1.09255 (6)	0.02135 (19)
H1AQ	1.036 (2)	0.382 (4)	1.0690 (14)	0.036 (4)*
H2AQ	0.886 (2)	0.481 (4)	1.0474 (16)	0.036 (4)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0180 (3)	0.0172 (4)	0.0200 (3)	0.0019 (2)	−0.0058 (2)	0.0000 (3)
O2	0.0176 (3)	0.0159 (4)	0.0225 (3)	−0.0008 (3)	−0.0025 (2)	−0.0012 (3)
O3	0.0305 (4)	0.0140 (4)	0.0190 (3)	−0.0014 (3)	−0.0075 (3)	−0.0001 (3)
C1	0.0132 (4)	0.0159 (5)	0.0146 (4)	−0.0004 (3)	0.0019 (3)	0.0004 (3)
C2	0.0164 (4)	0.0151 (5)	0.0159 (4)	0.0000 (3)	−0.0034 (3)	−0.0003 (3)
C3	0.0345 (6)	0.0222 (5)	0.0153 (4)	−0.0024 (4)	−0.0058 (4)	0.0027 (4)
N	0.0166 (4)	0.0189 (4)	0.0134 (4)	−0.0008 (3)	−0.0025 (3)	−0.0001 (3)
C4	0.0188 (5)	0.0267 (6)	0.0189 (4)	−0.0063 (4)	−0.0032 (3)	0.0044 (4)
C5	0.0185 (4)	0.0168 (4)	0.0142 (4)	−0.0008 (4)	−0.0013 (3)	−0.0008 (4)
C6	0.0183 (4)	0.0180 (5)	0.0130 (4)	−0.0022 (4)	−0.0028 (3)	−0.0011 (4)
C7	0.0260 (5)	0.0202 (5)	0.0176 (4)	0.0008 (4)	−0.0002 (4)	0.0001 (4)
C8	0.0313 (5)	0.0224 (5)	0.0206 (5)	−0.0027 (4)	−0.0060 (4)	0.0040 (4)
C9	0.0286 (5)	0.0327 (6)	0.0157 (4)	−0.0115 (4)	−0.0046 (4)	0.0054 (4)
C10	0.0247 (5)	0.0393 (7)	0.0169 (4)	−0.0032 (5)	0.0034 (4)	−0.0017 (5)
C11	0.0212 (4)	0.0278 (5)	0.0175 (4)	0.0009 (4)	0.0009 (3)	−0.0013 (4)
O1AQ	0.0194 (4)	0.0238 (4)	0.0205 (3)	0.0019 (3)	−0.0007 (3)	0.0038 (3)

Geometric parameters (Å, º)

O1—C1	1.2676 (12)	C4—H4C	0.980 (18)
O2—C1	1.2527 (12)	C5—C6	1.5164 (13)
O3—C2	1.4113 (12)	C5—H5	0.976 (16)
O3—H2O	0.87 (2)	C6—C11	1.3942 (13)
C1—C2	1.5335 (13)	C6—C7	1.3985 (15)
C2—C3	1.5312 (13)	C7—C8	1.3920 (16)
C2—H2C	0.976 (13)	C7—H7	0.988 (18)
C3—H3A	0.968 (17)	C8—C9	1.3909 (18)
C3—H3B	0.962 (19)	C8—H8	0.92 (2)
C3—H3C	1.00 (2)	C9—C10	1.3868 (19)
N—C5	1.4999 (12)	C9—H9	0.97 (2)
N—H12A	0.893 (16)	C10—C11	1.3963 (17)
N—H12B	0.890 (18)	C10—H10	0.922 (18)
N—H12C	0.875 (19)	C11—H11	0.99 (2)
C4—C5	1.5213 (13)	O1AQ—H1AQ	0.850 (19)
C4—H4A	0.966 (19)	O1AQ—H2AQ	0.82 (2)
C4—H4B	0.911 (18)
C2—O3—H2O	104.9 (12)	H4B—C4—H4C	108.6 (15)
O2—C1—O1	124.47 (9)	N—C5—C6	109.43 (8)
O2—C1—C2	117.47 (8)	N—C5—C4	108.98 (7)
O1—C1—C2	118.06 (8)	C6—C5—C4	113.96 (8)
O3—C2—C3	111.66 (8)	N—C5—H5	108.8 (8)
O3—C2—C1	109.24 (7)	C6—C5—H5	109.1 (8)
C3—C2—C1	109.80 (8)	C4—C5—H5	106.5 (8)
O3—C2—H2C	109.6 (8)	C11—C6—C7	118.77 (9)
C3—C2—H2C	109.3 (8)	C11—C6—C5	119.82 (9)
C1—C2—H2C	107.2 (8)	C7—C6—C5	121.41 (8)
C2—C3—H3A	110.5 (10)	C8—C7—C6	120.52 (10)
C2—C3—H3B	109.1 (9)	C8—C7—H7	120.1 (11)
H3A—C3—H3B	111.2 (14)	C6—C7—H7	119.4 (11)
C2—C3—H3C	111.0 (11)	C9—C8—C7	120.25 (11)
H3A—C3—H3C	107.5 (15)	C9—C8—H8	120.4 (11)
H3B—C3—H3C	107.4 (15)	C7—C8—H8	119.3 (11)
C5—N—H12A	109.7 (10)	C10—C9—C8	119.68 (10)
C5—N—H12B	116.3 (11)	C10—C9—H9	120.5 (11)
H12A—N—H12B	102.3 (14)	C8—C9—H9	119.6 (11)
C5—N—H12C	109.6 (9)	C9—C10—C11	120.14 (10)
H12A—N—H12C	111.4 (15)	C9—C10—H10	120.1 (12)
H12B—N—H12C	107.4 (14)	C11—C10—H10	119.7 (12)
C5—C4—H4A	111.2 (10)	C6—C11—C10	120.64 (11)
C5—C4—H4B	109.5 (9)	C6—C11—H11	121.3 (11)
H4A—C4—H4B	108.0 (14)	C10—C11—H11	118.1 (11)
C5—C4—H4C	113.6 (10)	H1AQ—O1AQ—H2AQ	108.5 (17)
H4A—C4—H4C	105.8 (14)
O2—C1—C2—O3	179.47 (8)	C11—C6—C7—C8	0.49 (14)
O1—C1—C2—O3	−1.40 (11)	C5—C6—C7—C8	179.90 (9)
O2—C1—C2—C3	−57.76 (11)	C6—C7—C8—C9	−1.05 (16)
O1—C1—C2—C3	121.36 (9)	C7—C8—C9—C10	1.17 (16)
N—C5—C6—C11	106.21 (10)	C8—C9—C10—C11	−0.75 (16)
C4—C5—C6—C11	−131.51 (9)	C7—C6—C11—C10	−0.07 (14)
N—C5—C6—C7	−73.20 (10)	C5—C6—C11—C10	−179.50 (9)
C4—C5—C6—C7	49.08 (12)	C9—C10—C11—C6	0.21 (16)