Structural relationships in crystals accommodating different stereoisomers of 2-amino-3-methylpentanoic acid

A reinvestigation of the crystal structure of the 1:1 mixture of the two racemates DL-isoleucine and DL-allo-isoleucine, with a detailed analysis of interatomic distances between alternative side-chain positions, reveals a systematic distribution of the four stereoisomers in this crystal. Two different molecular chains exist in the crystal and each such chain accommodates a single diastereomeric pair only (L-isoleucine:D-allo-isoleucine or D-isoleucine:L-allo-isoleucine). The crystal is built up by a stacking of such chains in two dimensions and three different packing modes for the two types of chains are discussed. Crystallization experiments of the two individual racemates in the 1:1 mixture of DL-isoleucine:DL-allo-isoleucine have been undertaken. The structure of the racemate DL-isoleucine is presented. The molecular arrangements in this racemate and the 1:1 DL-isoleucine:DL-allo-isoleucine mixture are closely related. Furthermore, the spontaneous resolution of enantiomers upon crystallization of the other racemate, DL-allo-isoleucine, is rationalized on the basis of the aforementioned analysis of interatomic distances in the 1:1 DL-isoleucine:DL-allo-isoleucine complex. Structural data for a new L-isoleucine: D-allo-isoleucine complex are also given.

Computing details

For all compounds, program(s) used to solve structure: SHELXTL (Sheldrick, 1995); program(s) used to refine structure: SHELXTL (Sheldrick, 1995).

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Crystal data

C6H13NO2	Z = 2
Mr = 131.17	F(000) = 144
Triclinic, P1	Dx = 1.255 Mg m^−3
a = 5.2289 (1) Å	Mo Kα radiation, λ = 0.71073 Å
b = 5.4102 (1) Å	Cell parameters from 4333 reflections
c = 13.1095 (3) Å	µ = 0.09 mm^−1
α = 96.332 (1)°	T = 150 K
β = 90.622 (1)°	Plate, colourless
γ = 109.493 (1)°	0.50 × 0.50 × 0.10 mm
V = 347.02 (1) Å^3

Data collection

Siemens SMART CCD diffractometer	5815 independent reflections
Radiation source: fine-focus sealed tube	4439 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.033
ω scans	θmax = 40°, θmin = 3.1°
Absorption correction: multi-scan (sheldrick, 1996)	h = −10→9
Tmin = 0.955, Tmax = 0.991	k = −9→11
8317 measured reflections	l = −26→21

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.058	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.170	H-atom parameters not defined?
S = 1.06	Calculated w = 1/[σ^2(Fo^2) + (0.0888P)^2 + 0.025P] where P = (Fo^2 + 2Fc^2)/3
5815 reflections	(Δ/σ)max = 0.001
101 parameters	Δρmax = 0.62 e Å^−3
0 restraints	Δρmin = −0.46 e Å^−3

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
O1	0.80323 (9)	0.75963 (8)	0.58960 (4)	0.01627 (9)
O2	0.36212 (9)	0.63846 (9)	0.62394 (4)	0.01616 (9)
N1	0.81846 (10)	0.26922 (9)	0.57840 (4)	0.01351 (8)
H1	0.988 (3)	0.389 (3)	0.6066 (10)	0.023 (3)*
H2	0.812 (3)	0.114 (3)	0.5854 (10)	0.024 (3)*
H3	0.803 (3)	0.282 (3)	0.5104 (10)	0.023 (3)*
C1	0.58380 (11)	0.59662 (10)	0.61346 (4)	0.01216 (8)
C2	0.58889 (10)	0.32193 (10)	0.63253 (4)	0.01191 (8)
H4	0.422 (2)	0.1918 (16)	0.6033 (4)	0.014*
C3	0.61101 (12)	0.29197 (11)	0.74779 (5)	0.01447 (9)
H5	0.6824 (9)	0.1440 (18)	0.75333 (8)	0.017*
C4	0.81181 (15)	0.54061 (14)	0.80856 (6)	0.02060 (12)
H6	0.9808 (15)	0.6004 (11)	0.7712 (5)	0.031*
H7	0.8542 (14)	0.5001 (6)	0.8772 (6)	0.031*
H8	0.730 (1)	0.6817 (13)	0.8165 (6)	0.031*
C5	0.33004 (15)	0.2148 (2)	0.79270 (6)	0.02330 (13)
H9	0.2639 (7)	0.3641 (15)	0.79461 (6)	0.028*
H10	0.2044 (12)	0.0679 (14)	0.7474 (4)	0.028*
C6	0.3293 (2)	0.1342 (2)	0.90085 (7)	0.0371 (2)
H11	0.1417 (19)	0.077 (2)	0.9240 (4)	0.056*
H12	0.444 (2)	0.2862 (17)	0.9484 (5)	0.056*
H13	0.402 (2)	−0.013 (2)	0.9001 (2)	0.056*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0163 (2)	0.01012 (14)	0.0230 (2)	0.00421 (11)	0.00542 (14)	0.00458 (13)
O2	0.0145 (2)	0.0146 (2)	0.0208 (2)	0.00693 (12)	0.00167 (13)	0.00182 (14)
N1	0.0159 (2)	0.01003 (15)	0.0154 (2)	0.00513 (12)	0.00445 (14)	0.00233 (13)
C1	0.0145 (2)	0.0095 (2)	0.0126 (2)	0.00435 (13)	0.00142 (14)	0.00099 (13)
C2	0.0131 (2)	0.0091 (2)	0.0135 (2)	0.00361 (12)	0.00200 (14)	0.00155 (13)
C3	0.0173 (2)	0.0129 (2)	0.0138 (2)	0.00547 (15)	0.0027 (2)	0.00282 (15)
C4	0.0230 (3)	0.0190 (2)	0.0170 (3)	0.0045 (2)	−0.0016 (2)	−0.0006 (2)
C5	0.0218 (3)	0.0258 (3)	0.0221 (3)	0.0059 (2)	0.0093 (2)	0.0078 (2)
C6	0.0444 (5)	0.0363 (4)	0.0186 (3)	−0.0033 (4)	0.0103 (3)	0.0066 (3)

Geometric parameters (Å, º)

O1—C1	1.2592 (7)	C3—H5	0.999 (12)
O2—C1	1.2591 (7)	C4—H6	0.989 (8)
N1—C2	1.4927 (7)	C4—H7	0.989 (8)
N1—H1	0.948 (13)	C4—H8	0.989 (8)
N1—H2	0.845 (14)	C5—C6	1.5282 (12)
N1—H3	0.906 (13)	C5—H9	0.977 (10)
C1—C2	1.5427 (7)	C5—H10	0.977 (10)
C2—C3	1.5445 (8)	C6—H11	0.987 (10)
C2—H4	0.963 (12)	C6—H12	0.987 (10)
C3—C5	1.5307 (9)	C6—H13	0.987 (10)
C3—C4	1.5328 (9)
C2—N1—H1	110.9 (8)	C2—C3—H5	107.43 (3)
C2—N1—H2	108.7 (9)	C3—C4—H6	109.47 (4)
H1—N1—H2	108.8 (11)	C3—C4—H7	109.47 (4)
C2—N1—H3	110.2 (8)	H6—C4—H7	109.5
H1—N1—H3	109.6 (11)	C3—C4—H8	109.47 (4)
H2—N1—H3	108.5 (12)	H6—C4—H8	109.5
O1—C1—O2	125.92 (5)	H7—C4—H8	109.5
O1—C1—C2	116.80 (5)	C6—C5—C3	113.28 (7)
O2—C1—C2	117.28 (5)	C6—C5—H9	108.92 (6)
N1—C2—C1	109.39 (4)	C3—C5—H9	108.92 (4)
N1—C2—C3	110.18 (5)	C6—C5—H10	108.92 (5)
C1—C2—C3	113.02 (4)	C3—C5—H10	108.92 (4)
N1—C2—H4	108.03 (3)	H9—C5—H10	107.7
C1—C2—H4	108.03 (3)	C5—C6—H11	109.47 (5)
C3—C2—H4	108.03 (3)	C5—C6—H12	109.47 (5)
C5—C3—C4	111.87 (6)	H11—C6—H12	109.5
C5—C3—C2	110.49 (5)	C5—C6—H13	109.47 (6)
C4—C3—C2	111.92 (5)	H11—C6—H13	109.5
C5—C3—H5	107.43 (4)	H12—C6—H13	109.5
C4—C3—H5	107.43 (4)
O1—C1—C2—N1	−22.95 (7)	N1—C2—C3—C4	81.48 (6)
O2—C1—C2—N1	157.62 (5)	N1—C2—C3—C5	−153.14 (5)
O1—C1—C2—C3	100.20 (6)	C1—C2—C3—C4	−41.24 (6)
O2—C1—C2—C3	−79.22 (6)	C4—C3—C5—C6	−64.80 (9)
C1—C2—C3—C5	84.14 (6)	C2—C3—C5—C6	169.79 (7)

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Crystal data

C6H13NO2	V = 351.42 (2) Å^3
Mr = 131.17	Z = 2
Triclinic, P1	F(000) = 144
Hall symbol: P 1	Dx = 1.240 Mg m^−3
a = 5.2438 (2) Å	Mo Kα radiation, λ = 0.71073 Å
b = 5.3978 (2) Å	Cell parameters from 3483 reflections
c = 13.2562 (6) Å	µ = 0.09 mm^−1
α = 93.042 (1)°	T = 140 K
β = 92.811 (1)°	Plate, colourless
γ = 109.897 (1)°	0.45 × 0.25 × 0.10 mm

Data collection

Siemens SMART CCD diffractometer	4029 independent reflections
Radiation source: fine-focus sealed tube	3746 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.010
ω scans	θmax = 32.5°, θmin = 1.5°
Absorption correction: multi-scan (sheldrick, 1996)	h = −8→5
Tmin = 0.959, Tmax = 0.991	k = −8→9
4788 measured reflections	l = −22→22

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	H-atom parameters not defined?
wR(F^2) = 0.097	Calculated w = 1/[σ^2(Fo^2) + (0.0675P)^2 + 0.0025P] where P = (Fo^2 + 2Fc^2)/3
S = 1.08	(Δ/σ)max = 0.001
4028 reflections	Δρmax = 0.44 e Å^−3
201 parameters	Δρmin = −0.22 e Å^−3
3 restraints	Absolute structure: Flack H D (1983), Acta Cryst. A39, 876-881
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.14 (64)

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
O1A	0.9524 (2)	0.6557 (2)	0.57652 (6)	0.0149 (2)
O2A	0.5127 (2)	0.5281 (2)	0.61114 (6)	0.01442 (15)
N1A	0.9645 (2)	0.1650 (2)	0.56582 (7)	0.0118 (2)
H1A	1.163 (7)	0.282 (7)	0.597 (2)	0.063 (8)*
H2A	0.963 (5)	−0.003 (5)	0.5731 (16)	0.033 (6)*
H3A	0.940 (5)	0.177 (4)	0.5070 (16)	0.026 (5)*
C1A	0.7340 (2)	0.4885 (2)	0.60067 (7)	0.0105 (2)
C2A	0.7406 (2)	0.2121 (2)	0.62044 (7)	0.0105 (2)
H4A	0.574 (3)	0.086 (3)	0.5937 (5)	0.013*
C3A	0.7765 (2)	0.1732 (2)	0.73401 (7)	0.0124 (2)
H5A	0.8479 (15)	0.025 (3)	0.73930 (13)	0.015*
C4A	0.9848 (3)	0.4177 (3)	0.79132 (9)	0.0184 (2)
H6A	1.145 (2)	0.4767 (15)	0.7546 (6)	0.028*
H7A	1.0310 (18)	0.3740 (8)	0.8573 (9)	0.028*
H8A	0.9087 (12)	0.5555 (19)	0.7979 (7)	0.028*
C5A	0.5015 (3)	0.0912 (3)	0.78135 (9)	0.0203 (2)
H9A	0.4383 (10)	0.238 (2)	0.78416 (10)	0.024*
H10A	0.373 (2)	−0.048 (2)	0.7389 (7)	0.024*
C6A	0.5155 (3)	−0.0009 (3)	0.88809 (9)	0.0303 (2)
H11A	0.327 (3)	−0.067 (3)	0.9129 (6)	0.045*
H12A	0.635 (3)	0.152 (2)	0.9351 (7)	0.045*
H13A	0.593 (3)	−0.148 (3)	0.8865 (2)	0.045*
O1B	0.3355 (2)	0.15514 (15)	0.40100 (6)	0.01413 (15)
O2B	0.7748 (2)	0.2815 (2)	0.36717 (6)	0.0144 (2)
N1B	0.3217 (2)	0.6441 (2)	0.41060 (7)	0.0117 (2)
H1B	0.173 (3)	0.536 (3)	0.3866 (10)	0.003 (3)*
H2B	0.327 (4)	0.810 (4)	0.4049 (13)	0.018 (4)*
H3B	0.339 (4)	0.620 (3)	0.4793 (13)	0.013 (4)*
C1B	0.5541 (2)	0.3217 (2)	0.37729 (7)	0.0108 (2)
C2B	0.5494 (2)	0.5993 (2)	0.35807 (7)	0.0109 (2)
H4B	0.715 (3)	0.726 (3)	0.3867 (6)	0.013*
C3B	0.5233 (2)	0.6409 (2)	0.24385 (8)	0.0141 (2)
H5B	0.4450 (16)	0.798 (3)	0.2368 (2)	0.017*
C4B	0.8033 (3)	0.7279 (3)	0.20184 (11)	0.0264 (3)
H6B	0.9269 (19)	0.884 (3)	0.2435 (8)	0.040*
H7B	0.7876 (6)	0.774 (3)	0.131 (1)	0.040*
H8B	0.8773 (16)	0.582 (2)	0.2037 (9)	0.040*
C5B	0.3228 (3)	0.3951 (3)	0.18385 (8)	0.0187 (2)
H9B	0.3994 (11)	0.249 (2)	0.18493 (8)	0.022*
H10B	0.149 (2)	0.3370 (8)	0.2182 (5)	0.022*
C6B	0.2612 (3)	0.4403 (3)	0.07347 (8)	0.0318 (3)
H11B	0.120 (3)	0.290 (2)	0.0433 (5)	0.048*
H12B	0.419 (2)	0.468 (3)	0.0376 (6)	0.048*
H13B	0.207 (3)	0.590 (3)	0.07145 (11)	0.048*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1A	0.0139 (4)	0.0090 (3)	0.0224 (4)	0.0041 (3)	0.0039 (3)	0.0037 (3)
O2A	0.0122 (3)	0.0130 (4)	0.0206 (3)	0.0077 (3)	0.0006 (3)	0.0023 (3)
N1A	0.0122 (4)	0.0089 (4)	0.0152 (3)	0.0045 (3)	0.0026 (3)	0.0019 (3)
C1A	0.0109 (4)	0.0085 (4)	0.0128 (3)	0.0044 (3)	−0.0001 (3)	0.0007 (3)
C2A	0.0102 (4)	0.0079 (4)	0.0139 (4)	0.0037 (3)	0.0007 (3)	0.0015 (3)
C3A	0.0127 (4)	0.0110 (4)	0.0144 (4)	0.0048 (4)	0.0015 (3)	0.0031 (3)
C4A	0.0182 (5)	0.0181 (5)	0.0170 (4)	0.0046 (4)	−0.0029 (3)	0.0002 (4)
C5A	0.0165 (5)	0.0228 (6)	0.0214 (4)	0.0049 (4)	0.0064 (4)	0.0072 (4)
C6A	0.0335 (6)	0.0328 (6)	0.0208 (4)	0.0044 (5)	0.0097 (4)	0.0084 (4)
O1B	0.0132 (3)	0.0085 (3)	0.0220 (3)	0.0047 (3)	0.0039 (3)	0.0038 (3)
O2B	0.0111 (3)	0.0138 (4)	0.0197 (3)	0.0063 (3)	−0.0003 (3)	0.0006 (3)
N1B	0.0131 (4)	0.0082 (4)	0.0152 (3)	0.0051 (3)	0.0022 (3)	0.0020 (3)
C1B	0.0122 (4)	0.0086 (4)	0.0122 (3)	0.0049 (3)	−0.0008 (3)	0.0007 (3)
C2B	0.0100 (4)	0.0082 (4)	0.0152 (4)	0.0038 (3)	0.0011 (3)	0.0020 (3)
C3B	0.0160 (5)	0.0125 (5)	0.0161 (4)	0.0069 (4)	0.0042 (3)	0.0050 (3)
C4B	0.0220 (6)	0.0297 (8)	0.0285 (6)	0.0072 (5)	0.0131 (5)	0.0112 (5)
C5B	0.0221 (5)	0.0188 (6)	0.0142 (4)	0.0062 (4)	−0.0010 (4)	0.0008 (4)
C6B	0.0401 (7)	0.0430 (7)	0.0151 (4)	0.0183 (6)	−0.0020 (4)	0.0030 (4)

Geometric parameters (Å, º)

O1A—C1A	1.2619 (12)	O1B—C1B	1.2589 (13)
O2A—C1A	1.2622 (13)	O2B—C1B	1.2602 (13)
N1A—C2A	1.4950 (15)	N1B—C2B	1.4932 (15)
N1A—H1A	1.06 (4)	N1B—H1B	0.84 (2)
N1A—H2A	0.92 (3)	N1B—H2B	0.89 (2)
N1A—H3A	0.79 (2)	N1B—H3B	0.93 (2)
C1A—C2A	1.5397 (15)	C1B—C2B	1.542 (2)
C2A—C3A	1.5425 (13)	C2B—C3B	1.5486 (14)
C2A—H4A	0.94 (2)	C2B—H4B	0.95 (2)
C3A—C4A	1.531 (2)	C3B—C4B	1.525 (2)
C3A—C5A	1.534 (2)	C3B—C5B	1.535 (2)
C3A—H5A	1.00 (2)	C3B—H5B	1.06 (2)
C4A—H6A	0.959 (12)	C4B—H6B	0.990 (14)
C4A—H7A	0.959 (12)	C4B—H7B	0.990 (13)
C4A—H8A	0.959 (12)	C4B—H8B	0.990 (13)
C5A—C6A	1.531 (2)	C5B—C6B	1.533 (2)
C5A—H9A	0.955 (14)	C5B—H9B	1.000 (14)
C5A—H10A	0.955 (15)	C5B—H10B	1.000 (14)
C6A—H11A	1.008 (14)	C6B—H11B	0.946 (14)
C6A—H12A	1.008 (14)	C6B—H12B	0.946 (14)
C6A—H13A	1.008 (14)	C6B—H13B	0.946 (14)
C2A—N1A—H1A	113.7 (16)	C2B—N1B—H1B	110.2 (10)
C2A—N1A—H2A	110.2 (15)	C2B—N1B—H2B	109.8 (12)
H1A—N1A—H2A	103 (3)	H1B—N1B—H2B	111.1 (16)
C2A—N1A—H3A	109.5 (17)	C2B—N1B—H3B	110.0 (12)
H1A—N1A—H3A	114 (2)	H1B—N1B—H3B	107.8 (14)
H2A—N1A—H3A	107 (2)	H2B—N1B—H3B	107.9 (16)
O1A—C1A—O2A	126.02 (10)	O1B—C1B—O2B	126.01 (10)
O1A—C1A—C2A	116.67 (9)	O1B—C1B—C2B	116.74 (9)
O2A—C1A—C2A	117.30 (8)	O2B—C1B—C2B	117.25 (9)
N1A—C2A—C1A	109.32 (8)	N1B—C2B—C1B	109.26 (8)
N1A—C2A—C3A	109.85 (8)	N1B—C2B—C3B	110.43 (9)
C1A—C2A—C3A	113.05 (8)	C1B—C2B—C3B	112.60 (8)
N1A—C2A—H4A	108.16 (6)	N1B—C2B—H4B	108.14 (6)
C1A—C2A—H4A	108.16 (5)	C1B—C2B—H4B	108.14 (5)
C3A—C2A—H4A	108.16 (5)	C3B—C2B—H4B	108.14 (6)
C4A—C3A—C5A	111.91 (10)	C4B—C3B—C5B	112.18 (11)
C4A—C3A—C2A	111.90 (8)	C4B—C3B—C2B	109.99 (10)
C5A—C3A—C2A	110.65 (9)	C5B—C3B—C2B	111.94 (8)
C4A—C3A—H5A	107.37 (7)	C4B—C3B—H5B	107.50 (8)
C5A—C3A—H5A	107.37 (7)	C5B—C3B—H5B	107.50 (7)
C2A—C3A—H5A	107.37 (5)	C2B—C3B—H5B	107.50 (6)
C3A—C4A—H6A	109.47 (6)	C3B—C4B—H6B	109.47 (8)
C3A—C4A—H7A	109.47 (6)	C3B—C4B—H7B	109.47 (7)
H6A—C4A—H7A	109.5	H6B—C4B—H7B	109.5
C3A—C4A—H8A	109.47 (7)	C3B—C4B—H8B	109.47 (8)
H6A—C4A—H8A	109.5	H6B—C4B—H8B	109.5
H7A—C4A—H8A	109.5	H7B—C4B—H8B	109.5
C6A—C5A—C3A	112.96 (11)	C6B—C5B—C3B	113.56 (11)
C6A—C5A—H9A	108.99 (8)	C6B—C5B—H9B	108.86 (8)
C3A—C5A—H9A	108.99 (7)	C3B—C5B—H9B	108.86 (7)
C6A—C5A—H10A	108.99 (7)	C6B—C5B—H10B	108.86 (8)
C3A—C5A—H10A	108.99 (7)	C3B—C5B—H10B	108.86 (6)
H9A—C5A—H10A	107.8	H9B—C5B—H10B	107.7
C5A—C6A—H11A	109.47 (7)	C5B—C6B—H11B	109.47 (7)
C5A—C6A—H12A	109.47 (7)	C5B—C6B—H12B	109.47 (8)
H11A—C6A—H12A	109.5	H11B—C6B—H12B	109.5
C5A—C6A—H13A	109.47 (8)	C5B—C6B—H13B	109.47 (8)
H11A—C6A—H13A	109.5	H11B—C6B—H13B	109.5
H12A—C6A—H13A	109.5	H12B—C6B—H13B	109.5
O1A—C1A—C2A—N1A	−23.81 (12)	O1B—C1B—C2B—N1B	22.43 (12)
O2A—C1A—C2A—N1A	156.97 (8)	O2B—C1B—C2B—N1B	−158.08 (8)
O1A—C1A—C2A—C3A	98.89 (10)	O1B—C1B—C2B—C3B	−100.66 (11)
O2A—C1A—C2A—C3A	−80.33 (11)	O2B—C1B—C2B—C3B	78.83 (11)
N1A—C2A—C3A—C4A	81.08 (11)	N1B—C2B—C3B—C4B	152.52 (11)
C1A—C2A—C3A—C4A	−41.33 (13)	C1B—C2B—C3B—C4B	−85.04 (12)
N1A—C2A—C3A—C5A	−153.38 (10)	N1B—C2B—C3B—C5B	−82.05 (12)
C1A—C2A—C3A—C5A	84.21 (11)	C1B—C2B—C3B—C5B	40.38 (13)
C4A—C3A—C5A—C6A	−65.37 (15)	C4B—C3B—C5B—C6B	−63.7 (2)
C2A—C3A—C5A—C6A	169.1 (1)	C2B—C3B—C5B—C6B	172.06 (10)

(5)

Crystal data

C6H13NO2	Z = 2
Mr = 131.17	F(000) = 144
Triclinic, P1	Dx = 1.235 Mg m^−3
a = 5.2493 (1) Å	Mo Kα radiation, λ = 0.71073 Å
b = 5.4006 (1) Å	Cell parameters from 6724 reflections
c = 13.2778 (2) Å	µ = 0.09 mm^−1
α = 92.9433 (6)°	T = 150 K
β = 92.8659 (5)°	Plate, colourless
γ = 109.8571 (7)°	0.75 × 0.55 × 0.30 mm
V = 352.66 (1) Å^3

Data collection

Siemens SMART CCD diffractometer	6187 independent reflections
Radiation source: fine-focus sealed tube	5540 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.021
ω scans	θmax = 40.0°, θmin = 3.1°
Absorption correction: multi-scan (sheldrick, 1996)	h = −10→10
Tmin = 0.933, Tmax = 0.973	k = −10→10
9079 measured reflections	l = −28→28

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)] = 0.061	H-atom parameters not defined?
wR(F^2) = 0.194	Calculated w = 1/[σ^2(Fo^2) + (0.0561P)^2 + 0.1597P] where P = (Fo^2 + 2Fc^2)/3
S = 1.25	(Δ/σ)max = 0.032
6187 reflections	Δρmax = 0.59 e Å^−3
116 parameters	Δρmin = −0.34 e Å^−3
0 restraints	Extinction correction: SHELXL, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 1.23 (7)

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)
O1	0.30806 (12)	0.75015 (11)	0.58772 (5)	0.01528 (10)
O2	−0.13094 (12)	0.62306 (12)	0.62196 (5)	0.01533 (10)
N1	0.32122 (13)	0.26020 (12)	0.57762 (5)	0.01253 (10)
H1	0.490 (5)	0.363 (5)	0.6040 (18)	0.034 (5)*
H2	0.328 (4)	0.098 (4)	0.5816 (15)	0.021 (4)*
H3	0.288 (5)	0.280 (5)	0.5182 (18)	0.031 (5)*
C1	0.08990 (14)	0.58294 (13)	0.61158 (5)	0.01132 (10)
C2	0.09599 (13)	0.30626 (13)	0.63118 (5)	0.01136 (10)
H4	−0.056 (3)	0.191 (2)	0.6059 (5)	0.014*
C3	0.1269 (2)	0.26586 (15)	0.74491 (6)	0.01437 (11)
H5	0.2041 (13)	0.109 (3)	0.75126 (12)	0.017*
C4	0.3310 (2)	0.5107 (2)	0.80368 (7)	0.02080 (15)	0.50
H6	0.476 (5)	0.580 (4)	0.7665 (14)	0.031*	0.50
H7	0.388 (4)	0.4641 (17)	0.863 (2)	0.031*	0.50
H8	0.250 (3)	0.633 (4)	0.8160 (18)	0.031*	0.50
C5	−0.1495 (2)	0.1817 (2)	0.78999 (9)	0.0256 (2)	0.50
H9	−0.290 (6)	0.024 (6)	0.7432 (18)	0.031*	0.50
H10	−0.223 (3)	0.342 (6)	0.79204 (12)	0.031*	0.50
C6	−0.1310 (6)	0.0921 (6)	0.8984 (2)	0.0337 (5)	0.50
H11	−0.316 (6)	0.031 (7)	0.9246 (13)	0.051*	0.50
H12	−0.007 (7)	0.244 (5)	0.9437 (16)	0.051*	0.50
H13	−0.058 (7)	−0.056 (7)	0.8969 (4)	0.051*	0.50
C4'	−0.1495 (2)	0.1817 (2)	0.78999 (9)	0.0256 (2)	0.50
H6'	−0.262 (6)	0.037 (4)	0.755 (3)	0.038*	0.50
H7'	−0.219 (2)	0.312 (8)	0.787 (3)	0.038*	0.50
H8'	−0.130 (4)	0.148 (6)	0.855 (3)	0.038*	0.50
C5'	0.3310 (2)	0.5107 (2)	0.80368 (7)	0.02080 (15)	0.50
H9'	0.2601 (6)	0.661 (3)	0.8007 (7)	0.025*	0.50
H10'	0.507 (5)	0.5621 (12)	0.7704 (9)	0.025*	0.50
C6'	0.3840 (7)	0.4649 (7)	0.9153 (2)	0.0344 (5)	0.50
H11'	0.535 (7)	0.603 (6)	0.9439 (12)	0.052*	0.50
H12'	0.416 (7)	0.306 (6)	0.9190 (3)	0.052*	0.50
H13'	0.233 (6)	0.458 (7)	0.9505 (13)	0.052*	0.50

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0151 (2)	0.0096 (2)	0.0221 (2)	0.00470 (14)	0.0046 (2)	0.00406 (15)
O2	0.0128 (2)	0.0146 (2)	0.0206 (2)	0.0074 (2)	0.0003 (2)	0.0016 (2)
N1	0.0143 (2)	0.0096 (2)	0.0149 (2)	0.00525 (15)	0.0030 (2)	0.00215 (14)
C1	0.0122 (2)	0.0096 (2)	0.0130 (2)	0.0050 (2)	0.0000 (2)	0.00119 (15)
C2	0.0112 (2)	0.0089 (2)	0.0143 (2)	0.00371 (15)	0.0011 (2)	0.00182 (15)
C3	0.0166 (3)	0.0131 (2)	0.0149 (2)	0.0064 (2)	0.0030 (2)	0.0043 (2)
C4	0.0238 (4)	0.0207 (3)	0.0160 (3)	0.0059 (3)	−0.0025 (2)	0.0005 (2)
C5	0.0220 (4)	0.0288 (4)	0.0265 (4)	0.0069 (3)	0.0111 (3)	0.0101 (3)
C6	0.0377 (12)	0.0378 (12)	0.0213 (8)	0.0049 (9)	0.0111 (8)	0.0101 (8)
C4'	0.0220 (4)	0.0288 (4)	0.0265 (4)	0.0069 (3)	0.0111 (3)	0.0101 (3)
C5'	0.0238 (4)	0.0207 (3)	0.0160 (3)	0.0059 (3)	−0.0025 (2)	0.0005 (2)
C6'	0.0441 (14)	0.0478 (15)	0.0149 (7)	0.0208 (12)	−0.0014 (8)	0.0033 (8)

Geometric parameters (Å, º)

O1—C1	1.2611 (9)	C3—C4'	1.5289 (13)
O2—C1	1.2623 (9)	C3—C5'	1.5338 (12)
N1—C2	1.4937 (9)	C5—H9	1.06 (4)
N1—H1	0.91 (2)	C5—H10	1.06 (4)
N1—H2	0.89 (2)	C6—H11	1.00 (3)
N1—H3	0.82 (2)	C6—H12	1.00 (3)
C1—C2	1.5404 (9)	C6—H13	1.00 (3)
C2—C3	1.5453 (10)	C4'—H6'	0.89 (2)
C2—H4	0.87 (2)	C4'—H7'	0.89 (5)
C3—C4	1.5338 (12)	C4'—H8'	0.89 (3)
C3—C5	1.5289 (13)	C5'—C6'	1.542 (2)
C3—H5	1.06 (2)	C5'—H9'	1.002 (13)
C4—H6	0.91 (3)	C5'—H10'	1.00 (3)
C4—H7	0.91 (3)	C6'—H11'	0.93 (3)
C4—H8	0.91 (3)	C6'—H12'	0.93 (3)
C5—C6	1.551 (3)	C6'—H13'	0.93 (3)
C2—N1—H1	113.6 (15)	C3—C5—C6	111.44 (14)
C2—N1—H2	114.0 (13)	C3—C5—H9	109.34 (6)
H1—N1—H2	102.2 (19)	C6—C5—H9	109.34 (13)
C2—N1—H3	104.5 (16)	C3—C5—H10	109.34 (5)
H1—N1—H3	115 (2)	C6—C5—H10	109.34 (13)
H2—N1—H3	108 (2)	H9—C5—H10	108.0
O1—C1—O2	125.90 (6)	C5—C6—H11	109.47 (12)
O1—C1—C2	116.75 (6)	C5—C6—H12	109.47 (13)
O2—C1—C2	117.34 (6)	H11—C6—H12	109.5
N1—C2—C1	109.33 (5)	C5—C6—H13	109.47 (13)
N1—C2—C3	110.23 (6)	H11—C6—H13	109.47 (6)
C1—C2—C3	112.82 (6)	H12—C6—H13	109.5
N1—C2—H4	108.11 (4)	C3—C4'—H6'	109.4 (12)
C1—C2—H4	108.11 (4)	C3—C4'—H7'	109.5 (12)
C3—C2—H4	108.11 (4)	H6'—C4'—H7'	109.5 (19)
C4'—C3—C5'	111.76 (8)	C3—C4'—H8'	109.5 (9)
C5—C3—C4	111.76 (8)	H6'—C4'—H8'	110 (2)
C4'—C3—C2	110.60 (7)	H7'—C4'—H8'	109 (2)
C5—C3—C2	110.60 (7)	C3—C5'—C6'	112.67 (15)
C5'—C3—C2	112.04 (6)	C3—C5'—H9'	109.0 (5)
C4—C3—C2	112.04 (6)	C6'—C5'—H9'	109.0 (6)
C5—C3—H5	107.39 (5)	C3—C5'—H10'	109.0 (4)
C4—C3—H5	107.39 (5)	C6'—C5'—H10'	109.0 (5)
C2—C3—H5	107.39 (4)	H9'—C5'—H10'	107.9 (4)
C3—C4—H6	109.47 (5)	C5'—C6'—H11'	109.47 (14)
C3—C4—H7	109.47 (5)	C5'—C6'—H12'	109.47 (12)
H6—C4—H7	109.5	H11'—C6'—H12'	109.5
C3—C4—H8	109.47 (5)	C5'—C6'—H13'	109.47 (13)
H6—C4—H8	109.5	H11'—C6'—H13'	109.5
H7—C4—H8	109.5	H12'—C6'—H13'	109.47 (5)
O1—C1—C2—N1	−23.30 (9)	C4'—C3—C5—C6	0.100
O2—C1—C2—N1	157.53 (6)	C5'—C3—C5—C6	−64.5 (2)
O1—C1—C2—C3	99.75 (8)	C4—C3—C5—C6	−64.5 (2)
O2—C1—C2—C3	−79.42 (8)	C2—C3—C5—C6	169.89 (15)
C1—C2—C3—C4'	84.51 (8)	N1—C2—C3—C4'	−152.95 (7)
N1—C2—C3—C5	−152.95 (7)	N1—C2—C3—C5'	81.64 (8)
C1—C2—C3—C5	84.51 (8)	C4'—C3—C5'—C6'	60.5 (2)
C1—C2—C3—C5'	−40.90 (9)	C5—C3—C5'—C6'	60.5 (2)
N1—C2—C3—C4	81.64 (8)	C4—C3—C5'—C6'	0.94
C1—C2—C3—C4	−40.90 (9)	C2—C3—C5'—C6'	−174.73 (14)

(6)

Crystal data

C6H13NO2	F(000) = 288
Mr = 131.17	Dx = 1.227 Mg m^−3
Monoclinic, P21	Mo Kα radiation, λ = 0.71073 Å
a = 9.6706 (1) Å	Cell parameters from 7959 reflections
b = 5.2583 (1) Å	µ = 0.09 mm^−1
c = 14.1018 (2) Å	T = 150 K
β = 98.033 (1)°	Plate, colourless
V = 710.05 (2) Å^3	0.90 × 0.50 × 0.05 mm
Z = 4

Data collection

Siemens SMART CCD diffractometer	11372 independent reflections
Radiation source: fine-focus sealed tube	8967 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.029
ω scans	θmax = 40.0°, θmin = 1.5°
Absorption correction: multi-scan (sheldrick, 1996)	h = −16→20
Tmin = 0.921, Tmax = 0.995	k = −10→10
16583 measured reflections	l = −30→25

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)] = 0.048	H-atom parameters not defined?
wR(F^2) = 0.124	Calculated w = 1/[σ^2(Fo^2) + (0.0567P)^2 + 0.0061P] where P = (Fo^2 + 2Fc^2)/3
S = 1.06	(Δ/σ)max = −0.002
11371 reflections	Δρmax = 0.54 e Å^−3
196 parameters	Δρmin = −0.31 e Å^−3
1 restraint	Absolute structure: Flack H D (1983), Acta Cryst. A39, 876-881
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.63 (41)

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
O1A	0.64390 (5)	0.61873 (11)	0.58600 (4)	0.01513 (8)
O2A	0.73315 (5)	0.99335 (10)	0.63843 (4)	0.01703 (9)
N1A	0.89125 (6)	0.40288 (11)	0.57706 (4)	0.01317 (8)
H1A	0.8415 (14)	0.289 (3)	0.6025 (10)	0.026 (3)*
H2A	0.9777 (14)	0.344 (3)	0.5773 (9)	0.022 (3)*
H3A	0.8598 (14)	0.438 (3)	0.5172 (10)	0.028 (3)*
C1A	0.74430 (6)	0.76242 (12)	0.61626 (4)	0.01199 (9)
C2A	0.89164 (6)	0.64770 (12)	0.63091 (5)	0.01219 (9)
H4A	0.9554 (8)	0.7683 (15)	0.6038 (3)	0.015*
C3A	0.94808 (6)	0.60705 (13)	0.73830 (5)	0.01464 (10)
H5A	1.0226 (10)	0.4781 (17)	0.74185 (7)	0.018*
C4A	1.01413 (9)	0.8529 (2)	0.78089 (7)	0.0249 (2)
H6A	1.0824 (10)	0.9165 (11)	0.7401 (5)	0.037*
H7A	1.0626 (9)	0.8194 (5)	0.8465 (7)	0.037*
H8A	0.9403 (7)	0.9825 (13)	0.7837 (6)	0.037*
C5A	0.83562 (8)	0.5049 (2)	0.79516 (5)	0.01878 (11)
H9A	0.7623 (7)	0.6316 (12)	0.79429 (5)	0.023*
H10A	0.7943 (4)	0.3534 (15)	0.7635 (3)	0.023*
C6A	0.89085 (12)	0.4393 (2)	0.89933 (6)	0.0304 (2)
H11A	0.8170 (8)	0.351 (2)	0.9288 (4)	0.046*
H12A	0.9178 (11)	0.5978 (16)	0.9353 (4)	0.046*
H13A	0.9735 (11)	0.327 (2)	0.90132 (8)	0.046*
O1B	1.16317 (5)	1.22830 (11)	0.58923 (4)	0.01637 (9)
O2B	1.24741 (6)	1.62364 (11)	0.61395 (4)	0.02034 (10)
N1B	1.43383 (6)	1.04848 (12)	0.60816 (4)	0.01535 (9)
H1B	1.3871 (16)	0.917 (3)	0.6197 (11)	0.028 (3)*
H2B	1.5251 (14)	1.013 (3)	0.6248 (10)	0.024 (3)*
H3B	1.4143 (13)	1.084 (3)	0.5462 (10)	0.020 (3)*
C1B	1.25852 (6)	1.38685 (12)	0.61819 (5)	0.01262 (9)
C2B	1.39799 (6)	1.27240 (13)	0.66580 (5)	0.01338 (9)
H4B	1.4691 (10)	1.3963 (17)	0.66696 (5)	0.016*
C3B	1.38807 (7)	1.18566 (14)	0.76921 (5)	0.01600 (11)
H5B	1.313 (1)	1.0596 (17)	0.76637 (6)	0.019*
C4B	1.52314 (9)	1.0579 (2)	0.81456 (7)	0.0289 (2)
H6B	1.5448 (6)	0.9100 (19)	0.7736 (6)	0.043*
H7B	1.5117 (4)	0.9947 (19)	0.8805 (7)	0.043*
H8B	1.6021 (8)	1.1845 (14)	0.8195 (7)	0.043*
C5B	1.34993 (10)	1.4083 (2)	0.83059 (6)	0.0320 (2)
H9B	1.42612 (13)	1.5228 (2)	0.84033 (6)	0.038*
H10B	1.27286 (11)	1.4962 (2)	0.79688 (9)	0.038*
C6B	1.31314 (10)	1.3257 (2)	0.92814 (7)	0.0469 (3)
H11B	1.28998 (10)	1.4777 (2)	0.9645 (1)	0.070*
H12B	1.39405 (11)	1.2363 (2)	0.9645 (1)	0.070*
H13B	1.23156 (13)	1.2095 (2)	0.91861 (6)	0.070*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1A	0.01018 (15)	0.0166 (2)	0.0186 (2)	−0.00049 (15)	0.00182 (14)	−0.0012 (2)
O2A	0.0145 (2)	0.0113 (2)	0.0254 (2)	0.00250 (15)	0.0033 (2)	−0.0008 (2)
N1A	0.0111 (2)	0.0130 (2)	0.0156 (2)	0.00231 (15)	0.0023 (2)	−0.0012 (2)
C1A	0.0099 (2)	0.0121 (2)	0.0143 (2)	0.0016 (2)	0.0028 (2)	0.0009 (2)
C2A	0.0091 (2)	0.0110 (2)	0.0167 (2)	0.0007 (2)	0.0024 (2)	−0.0008 (2)
C3A	0.0122 (2)	0.0142 (2)	0.0168 (2)	0.0012 (2)	−0.0002 (2)	−0.0017 (2)
C4A	0.0231 (3)	0.0208 (3)	0.0285 (4)	−0.0044 (2)	−0.0050 (3)	−0.0056 (3)
C5A	0.0197 (3)	0.0213 (3)	0.0153 (2)	−0.0002 (2)	0.0026 (2)	0.0004 (2)
C6A	0.0397 (5)	0.0357 (5)	0.0152 (3)	0.0002 (4)	0.0016 (3)	0.0009 (3)
O1B	0.0103 (2)	0.0156 (2)	0.0226 (2)	0.00147 (14)	0.00016 (15)	−0.0042 (2)
O2B	0.0189 (2)	0.0119 (2)	0.0295 (3)	0.0034 (2)	0.0010 (2)	0.0020 (2)
N1B	0.0127 (2)	0.0169 (2)	0.0167 (2)	0.0054 (2)	0.0029 (2)	0.0018 (2)
C1B	0.0107 (2)	0.0120 (2)	0.0151 (2)	0.0018 (2)	0.0016 (2)	0.0000 (2)
C2B	0.0097 (2)	0.0139 (2)	0.0163 (2)	0.0006 (2)	0.0014 (2)	0.0009 (2)
C3B	0.0125 (2)	0.0200 (3)	0.0152 (2)	−0.0011 (2)	0.0010 (2)	0.0011 (2)
C4B	0.0201 (3)	0.0423 (5)	0.0237 (3)	0.0078 (3)	0.0015 (3)	0.0132 (3)
C5B	0.0406 (5)	0.0346 (5)	0.0201 (3)	0.0087 (4)	0.0019 (3)	−0.0065 (3)
C6B	0.0505 (6)	0.0718 (10)	0.0192 (4)	0.0068 (7)	0.0075 (4)	−0.0104 (5)

Geometric parameters (Å, º)

O1A—C1A	1.2569 (8)	O1B—C1B	1.2676 (8)
O2A—C1A	1.2623 (8)	O2B—C1B	1.2504 (9)
N1A—C2A	1.4944 (8)	N1B—C2B	1.4986 (9)
N1A—H1A	0.876 (15)	N1B—H1B	0.85 (2)
N1A—H2A	0.891 (14)	N1B—H2B	0.901 (14)
N1A—H3A	0.876 (15)	N1B—H3B	0.888 (13)
C1A—C2A	1.5344 (8)	C1B—C2B	1.5424 (8)
C2A—C3A	1.5512 (9)	C2B—C3B	1.5437 (9)
C2A—H4A	0.997 (12)	C2B—H4B	0.946 (13)
C3A—C4A	1.5271 (11)	C3B—C4B	1.5275 (11)
C3A—C5A	1.5356 (10)	C3B—C5B	1.5316 (11)
C3A—H5A	0.986 (13)	C3B—H5B	0.980 (13)
C4A—H6A	0.992 (9)	C4B—H6B	1.008 (10)
C4A—H7A	0.992 (9)	C4B—H7B	1.008 (10)
C4A—H8A	0.992 (9)	C4B—H8B	1.008 (10)
C5A—C6A	1.5306 (11)	C5B—C6B	1.5312 (14)
C5A—H9A	0.972 (9)	C5B—H9B	0.95
C5A—H10A	0.972 (9)	C5B—H10B	0.95
C6A—H11A	0.991 (10)	C6B—H11B	0.99
C6A—H12A	0.991 (10)	C6B—H12B	0.99
C6A—H13A	0.991 (10)	C6B—H13B	0.99
C2A—N1A—H1A	110.2 (10)	C2B—N1B—H1B	111.4 (10)
C2A—N1A—H2A	111.1 (9)	C2B—N1B—H2B	108.2 (10)
H1A—N1A—H2A	109.3 (13)	H1B—N1B—H2B	108.1 (14)
C2A—N1A—H3A	106.6 (11)	C2B—N1B—H3B	109.6 (9)
H1A—N1A—H3A	113.6 (13)	H1B—N1B—H3B	108.2 (13)
H2A—N1A—H3A	106.0 (12)	H2B—N1B—H3B	111.4 (12)
O1A—C1A—O2A	125.00 (6)	O2B—C1B—O1B	125.86 (6)
O1A—C1A—C2A	117.91 (6)	O2B—C1B—C2B	118.25 (6)
O2A—C1A—C2A	117.05 (5)	O1B—C1B—C2B	115.85 (6)
N1A—C2A—C1A	109.51 (5)	N1B—C2B—C1B	108.96 (5)
N1A—C2A—C3A	110.67 (5)	N1B—C2B—C3B	109.26 (6)
C1A—C2A—C3A	112.28 (5)	C1B—C2B—C3B	111.13 (5)
N1A—C2A—H4A	108.09 (3)	N1B—C2B—H4B	109.15 (3)
C1A—C2A—H4A	108.09 (3)	C1B—C2B—H4B	109.15 (3)
C3A—C2A—H4A	108.09 (3)	C3B—C2B—H4B	109.15 (4)
C4A—C3A—C5A	112.25 (6)	C4B—C3B—C5B	111.04 (7)
C4A—C3A—C2A	109.76 (6)	C4B—C3B—C2B	111.30 (6)
C5A—C3A—C2A	112.31 (5)	C5B—C3B—C2B	111.08 (7)
C4A—C3A—H5A	107.42 (4)	C4B—C3B—H5B	107.75 (5)
C5A—C3A—H5A	107.42 (4)	C5B—C3B—H5B	107.75 (5)
C2A—C3A—H5A	107.42 (3)	C2B—C3B—H5B	107.75 (3)
C3A—C4A—H6A	109.47 (5)	C3B—C4B—H6B	109.47 (5)
C3A—C4A—H7A	109.47 (4)	C3B—C4B—H7B	109.47 (4)
H6A—C4A—H7A	109.5	H6B—C4B—H7B	109.5
C3A—C4A—H8A	109.47 (4)	C3B—C4B—H8B	109.47 (5)
H6A—C4A—H8A	109.5	H6B—C4B—H8B	109.5
H7A—C4A—H8A	109.5	H7B—C4B—H8B	109.5
C6A—C5A—C3A	113.72 (7)	C6B—C5B—C3B	113.29 (5)
C6A—C5A—H9A	108.82 (5)	C6B—C5B—H9B	108.9
C3A—C5A—H9A	108.82 (4)	C3B—C5B—H9B	108.92 (4)
C6A—C5A—H10A	108.82 (5)	C6B—C5B—H10B	108.9
C3A—C5A—H10A	108.82 (4)	C3B—C5B—H10B	108.92 (4)
H9A—C5A—H10A	107.7	H9B—C5B—H10B	107.7
C5A—C6A—H11A	109.47 (5)	C5B—C6B—H11B	109.5
C5A—C6A—H12A	109.47 (5)	C5B—C6B—H12B	109.5
H11A—C6A—H12A	109.5	H11B—C6B—H12B	109.5
C5A—C6A—H13A	109.47 (5)	C5B—C6B—H13B	109.5
H11A—C6A—H13A	109.5	H11B—C6B—H13B	109.5
H12A—C6A—H13A	109.5	H12B—C6B—H13B	109.5
O1A—C1A—C2A—N1A	17.68 (8)	O2B—C1B—C2B—N1B	−138.86 (7)
O2A—C1A—C2A—N1A	−164.38 (5)	O1B—C1B—C2B—N1B	43.22 (7)
O1A—C1A—C2A—C3A	−105.68 (6)	O2B—C1B—C2B—C3B	100.70 (7)
O2A—C1A—C2A—C3A	72.27 (7)	O1B—C1B—C2B—C3B	−77.23 (7)
N1A—C2A—C3A—C4A	152.47 (6)	N1B—C2B—C3B—C4B	56.35 (8)
C1A—C2A—C3A—C4A	−84.83 (7)	C1B—C2B—C3B—C4B	176.62 (7)
N1A—C2A—C3A—C5A	−81.92 (7)	N1B—C2B—C3B—C5B	−179.37 (6)
C1A—C2A—C3A—C5A	40.78 (8)	C1B—C2B—C3B—C5B	−59.10 (7)
C4A—C3A—C5A—C6A	−61.08 (9)	C4B—C3B—C5B—C6B	−65.87 (6)
C2A—C3A—C5A—C6A	174.68 (7)	C2B—C3B—C5B—C6B	169.71 (3)