Conformational study of the 3,6-di­hydro-2H-1,4-oxazin-2-one fragment in 8-tert-butyl-7-meth­oxy-8-methyl-9-oxa-6-aza­spiro­[4.5]decane-2,10-dione stereoisomers

Unnatural cyclic α-amino acids play an important role in the search for bio­logically active compounds and macromolecules. Enanti­omers of natural amino acids with a D configuration are not naturally encoded, but can be chemically synthesized. The crystal structures of two enanti­omers obtained by a method of stereoselective synthesis, namely (5R,8S)-8-tert-butyl-7-meth­oxy-8-methyl-9-oxa-6-aza­spiro­[4.5]decane-2,10-dione, (1), and (5S,8R)-8-tert-butyl-7-meth­oxy-8-methyl-9-oxa-6-aza­spiro­[4.5]decane-2,10-dione, (2), both C₁₄H₂₁NO₄, were determined by X-ray diffraction. Both enanti­omers crystallize isostructurally in the space group P2₁, with one mol­ecule in the asymmetric unit and with the same packing motif. The crystal structures are stabilized by C—H...O hydrogen bonds, resulting in the formation of chains along the [100] and [010] directions. The conformation of the 3,6-di­hydro-2H-1,4-oxazin-2-one fragment was compared with other crystal structures possessing this heterocyclic moiety. The comparison showed that the title compounds are not exceptional among structures containing the 3,6-di­hydro-2H-1,4-oxazin-2-one fragment. The planar moiety was more frequently observed in derivatives in which this fragment was not condensed with other rings.

Computing details

Data collection: CrysAlis PRO (Rigaku OD, 2015) for (1); CrysAlis PRO (Agilent, 2014) for (2). Cell refinement: CrysAlis PRO (Rigaku OD, 2015) for (1); CrysAlis PRO (Agilent, 2014) for (2). Data reduction: CrysAlis PRO (Rigaku OD, 2015) for (1); CrysAlis PRO (Agilent, 2014) for (2). For both compounds, program(s) used to refine structure: SIR97 (Altomare et al., 1999), SHELXL97 (Sheldrick, 2008) and SHELXL2014 (Sheldrick, 2015); molecular graphics: ORTEP-3 (Farrugia, 2012) and Mercury (Macrae et al., 2006); software used to prepare material for publication: publCIF (Westrip, 2010).

(1) (5R,8S)-8-tert-Butyl-7-methoxy-8-methyl-9-oxa-6-azaspiro[4.5]decan-2,10-dione

Crystal data

C14H21NO4	F(000) = 288
Mr = 267.32	Dx = 1.218 Mg m^−3
Monoclinic, P21	Cu Kα radiation, λ = 1.54184 Å
Hall symbol: P 2yb	Cell parameters from 7013 reflections
a = 8.7136 (2) Å	θ = 3.4–71.3°
b = 6.3606 (2) Å	µ = 0.73 mm^−1
c = 13.3613 (3) Å	T = 293 K
β = 100.220 (2)°	Block, colourless
V = 728.78 (3) Å^3	0.3 × 0.2 × 0.15 mm
Z = 2

Data collection

Rigaku Oxford Diffraction SuperNova Dual Source diffractometer with an Atlas detector	2784 independent reflections
Radiation source: micro-focus sealed X-ray tube	2687 reflections with I > 2σ(I)
Mirror monochromator	Rint = 0.031
Detector resolution: 10.3756 pixels mm^-1	θmax = 71.3°, θmin = 3.4°
ω scans	h = −10→10
Absorption correction: gaussian (CrysAlis PRO (Rigaku OD, 2015)	k = −7→7
Tmin = 0.67, Tmax = 0.789	l = −16→16
9732 measured reflections

Refinement

Refinement on F^2	H-atom parameters constrained
Least-squares matrix: full	w = 1/[σ^2(Fo^2) + (0.0495P)^2 + 0.0486P] where P = (Fo^2 + 2Fc^2)/3
R[F^2 > 2σ(F^2)] = 0.032	(Δ/σ)max < 0.001
wR(F^2) = 0.087	Δρmax = 0.14 e Å^−3
S = 1.04	Δρmin = −0.12 e Å^−3
2784 reflections	Extinction correction: SHELXL2014 (Sheldrick, 2015), Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
178 parameters	Extinction coefficient: 0.036 (4)
1 restraint	Absolute structure: Flack x determined using 1165 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons & Flack, 2004)
Hydrogen site location: inferred from neighbouring sites	Absolute structure parameter: 0.05 (9)

Special details

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
C8	0.7582 (2)	−0.0099 (3)	0.77356 (13)	0.0518 (4)
O9	0.91198 (16)	−0.1048 (2)	0.80511 (11)	0.0625 (4)
C10	1.0452 (2)	−0.0238 (3)	0.78789 (14)	0.0540 (4)
C5	1.04114 (19)	0.1531 (3)	0.71098 (12)	0.0469 (4)
N6	0.88669 (16)	0.2157 (2)	0.65914 (10)	0.0450 (3)
C7	0.76752 (19)	0.1439 (3)	0.68780 (12)	0.0457 (4)
C12	0.6530 (3)	−0.1922 (5)	0.73256 (19)	0.0778 (7)
H12A	0.6587	−0.2993	0.7837	0.117*
H12B	0.6863	−0.2491	0.6734	0.117*
H12C	0.5475	−0.1434	0.7147	0.117*
C13	0.7148 (2)	0.0970 (4)	0.87027 (14)	0.0623 (6)
C14	0.7210 (4)	−0.0686 (7)	0.9554 (2)	0.1028 (11)
H14A	0.7022	−0.0015	1.0164	0.154*
H14B	0.822	−0.1336	0.9679	0.154*
H14C	0.6427	−0.1737	0.9348	0.154*
C15	0.8297 (3)	0.2731 (6)	0.90700 (19)	0.0885 (9)
H15A	0.7987	0.3428	0.964	0.133*
H15B	0.8306	0.3723	0.853	0.133*
H15C	0.9322	0.215	0.9272	0.133*
C16	0.5514 (3)	0.1913 (6)	0.8486 (2)	0.0871 (9)
H16A	0.5449	0.2918	0.7945	0.131*
H16B	0.5301	0.2599	0.9087	0.131*
H16C	0.4764	0.0816	0.8292	0.131*
O7	0.62354 (14)	0.1949 (3)	0.63816 (9)	0.0572 (4)
C11	0.6178 (2)	0.3215 (4)	0.54812 (15)	0.0606 (5)
H11A	0.6651	0.2462	0.4992	0.091*
H11B	0.6734	0.4505	0.5656	0.091*
H11C	0.5112	0.3523	0.5195	0.091*
O10	1.16585 (18)	−0.0998 (3)	0.83021 (13)	0.0809 (6)
C4	1.1303 (2)	0.3520 (3)	0.75557 (15)	0.0578 (5)
H4A	1.0647	0.4405	0.7895	0.069*
H4B	1.2233	0.3146	0.8036	0.069*
C3	1.1724 (3)	0.4627 (4)	0.66307 (18)	0.0701 (6)
H3A	1.0942	0.567	0.6371	0.084*
H3B	1.2728	0.5318	0.6804	0.084*
C2	1.1780 (2)	0.2925 (4)	0.58571 (15)	0.0579 (5)
C1	1.1331 (2)	0.0863 (4)	0.62779 (14)	0.0533 (4)
H1A	1.2248	0.0053	0.6564	0.064*
H1B	1.0687	0.0036	0.5755	0.064*
O2	1.2125 (2)	0.3169 (4)	0.50296 (14)	0.0856 (6)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C8	0.0493 (9)	0.0616 (11)	0.0453 (9)	−0.0009 (8)	0.0106 (7)	0.0078 (8)
O9	0.0619 (8)	0.0647 (9)	0.0644 (8)	0.0124 (7)	0.0206 (6)	0.0245 (7)
C10	0.0542 (10)	0.0616 (11)	0.0472 (9)	0.0104 (9)	0.0117 (7)	0.0076 (8)
C5	0.0457 (8)	0.0531 (10)	0.0416 (8)	0.0030 (7)	0.0067 (6)	0.0033 (7)
N6	0.0459 (7)	0.0483 (8)	0.0401 (7)	0.0012 (6)	0.0058 (5)	0.0033 (6)
C7	0.0468 (9)	0.0512 (10)	0.0382 (8)	0.0016 (7)	0.0054 (6)	0.0003 (7)
C12	0.0902 (16)	0.0731 (15)	0.0710 (13)	−0.0245 (14)	0.0168 (12)	0.0070 (13)
C13	0.0527 (9)	0.0942 (16)	0.0414 (8)	0.0061 (11)	0.0124 (7)	0.0066 (10)
C14	0.105 (2)	0.149 (3)	0.0607 (14)	0.022 (2)	0.0338 (14)	0.0396 (18)
C15	0.0818 (15)	0.124 (2)	0.0620 (13)	−0.0082 (16)	0.0184 (11)	−0.0339 (15)
C16	0.0619 (12)	0.132 (3)	0.0710 (14)	0.0202 (15)	0.0216 (10)	0.0025 (16)
O7	0.0456 (6)	0.0755 (9)	0.0488 (7)	0.0002 (6)	0.0041 (5)	0.0097 (6)
C11	0.0565 (10)	0.0712 (13)	0.0504 (10)	0.0036 (10)	−0.0007 (8)	0.0116 (10)
O10	0.0643 (9)	0.1032 (13)	0.0752 (10)	0.0257 (9)	0.0124 (7)	0.0369 (10)
C4	0.0520 (9)	0.0655 (13)	0.0539 (10)	−0.0045 (9)	0.0037 (7)	−0.0103 (9)
C3	0.0709 (13)	0.0628 (13)	0.0773 (15)	−0.0144 (11)	0.0149 (11)	−0.0001 (11)
C2	0.0480 (9)	0.0673 (12)	0.0604 (11)	0.0052 (9)	0.0148 (8)	0.0107 (10)
C1	0.0525 (9)	0.0604 (11)	0.0482 (9)	0.0062 (9)	0.0125 (7)	0.0028 (8)
O2	0.0998 (12)	0.0915 (12)	0.0765 (10)	0.0156 (11)	0.0460 (9)	0.0243 (10)

Geometric parameters (Å, º)

C8—O9	1.462 (2)	C15—H15A	0.96
C8—C12	1.519 (3)	C15—H15B	0.96
C8—C7	1.520 (2)	C15—H15C	0.96
C8—C13	1.565 (3)	C16—H16A	0.96
O9—C10	1.327 (3)	C16—H16B	0.96
C10—O10	1.203 (2)	C16—H16C	0.96
C10—C5	1.520 (3)	O7—C11	1.441 (2)
C5—N6	1.456 (2)	C11—H11A	0.96
C5—C1	1.541 (2)	C11—H11B	0.96
C5—C4	1.548 (3)	C11—H11C	0.96
N6—C7	1.255 (2)	C4—C3	1.523 (3)
C7—O7	1.351 (2)	C4—H4A	0.97
C12—H12A	0.96	C4—H4B	0.97
C12—H12B	0.96	C3—C2	1.503 (3)
C12—H12C	0.96	C3—H3A	0.97
C13—C15	1.524 (4)	C3—H3B	0.97
C13—C16	1.525 (3)	C2—O2	1.206 (2)
C13—C14	1.544 (4)	C2—C1	1.506 (3)
C14—H14A	0.96	C1—H1A	0.97
C14—H14B	0.96	C1—H1B	0.97
C14—H14C	0.96
O9—C8—C12	104.63 (19)	C13—C15—H15B	109.5
O9—C8—C7	108.34 (14)	H15A—C15—H15B	109.5
C12—C8—C7	109.20 (16)	C13—C15—H15C	109.5
O9—C8—C13	106.55 (14)	H15A—C15—H15C	109.5
C12—C8—C13	114.24 (17)	H15B—C15—H15C	109.5
C7—C8—C13	113.32 (18)	C13—C16—H16A	109.5
C10—O9—C8	125.09 (15)	C13—C16—H16B	109.5
O10—C10—O9	118.72 (19)	H16A—C16—H16B	109.5
O10—C10—C5	121.94 (18)	C13—C16—H16C	109.5
O9—C10—C5	119.24 (16)	H16A—C16—H16C	109.5
N6—C5—C10	115.66 (15)	H16B—C16—H16C	109.5
N6—C5—C1	106.71 (13)	C7—O7—C11	115.83 (14)
C10—C5—C1	109.34 (15)	O7—C11—H11A	109.5
N6—C5—C4	108.54 (15)	O7—C11—H11B	109.5
C10—C5—C4	113.26 (15)	H11A—C11—H11B	109.5
C1—C5—C4	102.30 (15)	O7—C11—H11C	109.5
C7—N6—C5	120.02 (15)	H11A—C11—H11C	109.5
N6—C7—O7	120.63 (16)	H11B—C11—H11C	109.5
N6—C7—C8	128.47 (15)	C3—C4—C5	104.02 (15)
O7—C7—C8	110.85 (14)	C3—C4—H4A	111
C8—C12—H12A	109.5	C5—C4—H4A	111
C8—C12—H12B	109.5	C3—C4—H4B	111
H12A—C12—H12B	109.5	C5—C4—H4B	111
C8—C12—H12C	109.5	H4A—C4—H4B	109
H12A—C12—H12C	109.5	C2—C3—C4	105.49 (19)
H12B—C12—H12C	109.5	C2—C3—H3A	110.6
C15—C13—C16	108.0 (3)	C4—C3—H3A	110.6
C15—C13—C14	109.2 (2)	C2—C3—H3B	110.6
C16—C13—C14	108.5 (2)	C4—C3—H3B	110.6
C15—C13—C8	110.12 (16)	H3A—C3—H3B	108.8
C16—C13—C8	111.65 (17)	O2—C2—C3	125.6 (2)
C14—C13—C8	109.3 (2)	O2—C2—C1	125.3 (2)
C13—C14—H14A	109.5	C3—C2—C1	109.15 (16)
C13—C14—H14B	109.5	C2—C1—C5	103.42 (16)
H14A—C14—H14B	109.5	C2—C1—H1A	111.1
C13—C14—H14C	109.5	C5—C1—H1A	111.1
H14A—C14—H14C	109.5	C2—C1—H1B	111.1
H14B—C14—H14C	109.5	C5—C1—H1B	111.1
C13—C15—H15A	109.5	H1A—C1—H1B	109
C12—C8—O9—C10	137.0 (2)	O9—C8—C13—C15	63.4 (2)
C7—C8—O9—C10	20.6 (3)	C12—C8—C13—C15	178.4 (2)
C13—C8—O9—C10	−101.6 (2)	C7—C8—C13—C15	−55.7 (2)
C8—O9—C10—O10	169.22 (19)	O9—C8—C13—C16	−176.6 (2)
C8—O9—C10—C5	−14.3 (3)	C12—C8—C13—C16	−61.6 (3)
O10—C10—C5—N6	174.52 (19)	C7—C8—C13—C16	64.4 (3)
O9—C10—C5—N6	−1.8 (3)	O9—C8—C13—C14	−56.6 (2)
O10—C10—C5—C1	54.1 (3)	C12—C8—C13—C14	58.4 (2)
O9—C10—C5—C1	−122.26 (19)	C7—C8—C13—C14	−175.61 (19)
O10—C10—C5—C4	−59.3 (3)	N6—C7—O7—C11	4.3 (3)
O9—C10—C5—C4	124.4 (2)	C8—C7—O7—C11	−173.34 (17)
C10—C5—N6—C7	8.8 (2)	N6—C5—C4—C3	−73.95 (18)
C1—C5—N6—C7	130.67 (17)	C10—C5—C4—C3	156.16 (17)
C4—C5—N6—C7	−119.74 (18)	C1—C5—C4—C3	38.61 (19)
C5—N6—C7—O7	−177.67 (15)	C5—C4—C3—C2	−25.7 (2)
C5—N6—C7—C8	−0.5 (3)	C4—C3—C2—O2	−177.5 (2)
O9—C8—C7—N6	−13.4 (3)	C4—C3—C2—C1	2.6 (2)
C12—C8—C7—N6	−126.8 (2)	O2—C2—C1—C5	−158.34 (19)
C13—C8—C7—N6	104.6 (2)	C3—C2—C1—C5	21.5 (2)
O9—C8—C7—O7	164.06 (15)	N6—C5—C1—C2	77.38 (18)
C12—C8—C7—O7	50.7 (2)	C10—C5—C1—C2	−156.85 (15)
C13—C8—C7—O7	−77.93 (19)	C4—C5—C1—C2	−36.53 (18)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C11—H11C···O2^i	0.96	2.58	3.476 (3)	155
C12—H12B···O2^ii	0.96	2.69	3.548 (3)	149
C15—H15A···O10^iii	0.96	2.74	3.596 (3)	149

Symmetry codes: (i) x−1, y, z; (ii) −x+2, y−1/2, −z+1; (iii) −x+2, y+1/2, −z+2.

(2) (5S,8R)-8-tert-Butyl-7-methoxy-8-methyl-9-oxa-6-azaspiro[4.5]decane-2,10-dione

Crystal data

C14H21NO4	F(000) = 288
Mr = 267.32	Dx = 1.224 Mg m^−3
Monoclinic, P21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2yb	Cell parameters from 2829 reflections
a = 8.7007 (3) Å	θ = 3.1–28.5°
b = 6.3466 (2) Å	µ = 0.09 mm^−1
c = 13.3458 (4) Å	T = 293 K
β = 100.243 (3)°	Block, colourless
V = 725.21 (4) Å^3	0.34 × 0.27 × 0.1 mm
Z = 2

Data collection

Rigaku Oxford Diffraction SuperNova Dual Source diffractometer with an Atlas detector	3396 independent reflections
Radiation source: SuperNova (Mo) X-ray Source	2235 reflections with I > 2σ(I)
Mirror monochromator	Rint = 0.033
Detector resolution: 10.3756 pixels mm^-1	θmax = 28.5°, θmin = 3.1°
ω scans	h = −11→11
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2014)	k = −8→8
Tmin = 0.800, Tmax = 1	l = −17→17
9804 measured reflections

Refinement

Refinement on F^2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F^2 > 2σ(F^2)] = 0.052	w = 1/[σ^2(Fo^2) + (0.0485P)^2 + 0.0692P] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.127	(Δ/σ)max < 0.001
S = 1.07	Δρmax = 0.12 e Å^−3
3396 reflections	Δρmin = −0.15 e Å^−3
172 parameters	Absolute structure: Flack x determined using 774 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons & Flack, 2004)
1 restraint	Absolute structure parameter: −0.5 (6)

Special details

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
O9	0.5881 (3)	0.4090 (4)	0.69474 (18)	0.0612 (7)
O10	0.3340 (3)	0.4043 (5)	0.6699 (2)	0.0793 (9)
O2	0.2874 (3)	−0.0121 (5)	0.9970 (2)	0.0829 (9)
O7	0.8769 (2)	0.1094 (4)	0.86184 (15)	0.0565 (6)
N6	0.6134 (3)	0.0889 (4)	0.84076 (18)	0.0447 (6)
C7	0.7325 (4)	0.1604 (5)	0.8123 (2)	0.0456 (8)
C8	0.7420 (4)	0.3133 (6)	0.7262 (2)	0.0503 (8)
C10	0.4541 (4)	0.3267 (6)	0.7122 (2)	0.0540 (9)
C5	0.4587 (3)	0.1519 (5)	0.7888 (2)	0.0449 (8)
C1	0.3674 (4)	0.2171 (6)	0.8721 (2)	0.0527 (8)
H1A	0.4322	0.2998	0.9244	0.063*
H1B	0.2756	0.2987	0.8437	0.063*
C13	0.7855 (4)	0.2079 (7)	0.6300 (2)	0.0624 (10)
C16	0.9484 (4)	0.1132 (9)	0.6517 (3)	0.0869 (14)
H16A	1.023	0.2215	0.6754	0.13*
H16B	0.9723	0.0522	0.5904	0.13*
H16C	0.9528	0.0061	0.7029	0.13*
C2	0.3223 (4)	0.0127 (7)	0.9141 (3)	0.0556 (9)
C14	0.6703 (5)	0.0321 (9)	0.5926 (3)	0.0847 (14)
H14A	0.5663	0.0885	0.5784	0.127*
H14B	0.6762	−0.0746	0.6442	0.127*
H14C	0.6957	−0.0285	0.5317	0.127*
C15	0.7788 (6)	0.3716 (10)	0.5444 (3)	0.0989 (17)
H15A	0.6763	0.4327	0.5299	0.148*
H15B	0.8014	0.3042	0.4843	0.148*
H15C	0.8545	0.4801	0.5655	0.148*
C4	0.3693 (4)	−0.0481 (6)	0.7447 (3)	0.0585 (10)
H4A	0.2758	−0.0109	0.6967	0.07*
H4B	0.4347	−0.1367	0.7105	0.07*
C12	0.8465 (5)	0.4980 (7)	0.7669 (3)	0.0764 (12)
H12A	0.9512	0.4486	0.7895	0.115*
H12B	0.8083	0.5616	0.8229	0.115*
H12C	0.8459	0.6004	0.7138	0.115*
C3	0.3281 (5)	−0.1588 (6)	0.8369 (3)	0.0695 (11)
H3A	0.2277	−0.2286	0.8197	0.083*
H3B	0.4067	−0.2628	0.863	0.083*
C11	0.8824 (4)	−0.0170 (7)	0.9517 (2)	0.0601 (9)
H11A	0.9892	−0.0449	0.9814	0.09*
H11B	0.829	−0.1478	0.9339	0.09*
H11C	0.8325	0.0571	0.9999	0.09*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O9	0.0588 (15)	0.0650 (15)	0.0630 (14)	0.0114 (13)	0.0191 (12)	0.0269 (12)
O10	0.0634 (17)	0.101 (2)	0.0735 (17)	0.0297 (16)	0.0121 (13)	0.0361 (16)
O2	0.097 (2)	0.0891 (19)	0.0738 (17)	0.0140 (17)	0.0450 (16)	0.0233 (16)
O7	0.0439 (12)	0.0766 (16)	0.0467 (12)	0.0005 (12)	0.0023 (10)	0.0106 (12)
N6	0.0424 (15)	0.0513 (16)	0.0401 (13)	0.0000 (13)	0.0061 (11)	0.0029 (12)
C7	0.0469 (19)	0.051 (2)	0.0376 (15)	0.0015 (16)	0.0029 (14)	0.0012 (15)
C8	0.0426 (18)	0.064 (2)	0.0443 (17)	−0.0006 (17)	0.0082 (14)	0.0079 (16)
C10	0.053 (2)	0.064 (2)	0.0455 (18)	0.0091 (19)	0.0114 (16)	0.0072 (17)
C5	0.0441 (17)	0.0508 (19)	0.0391 (15)	0.0016 (15)	0.0056 (13)	0.0031 (15)
C1	0.0512 (19)	0.062 (2)	0.0462 (18)	0.0065 (18)	0.0130 (15)	0.0041 (17)
C13	0.052 (2)	0.095 (3)	0.0408 (17)	0.005 (2)	0.0110 (15)	0.0073 (19)
C16	0.059 (2)	0.135 (4)	0.070 (2)	0.020 (3)	0.0202 (19)	0.002 (3)
C2	0.0433 (18)	0.065 (2)	0.060 (2)	0.0073 (17)	0.0136 (16)	0.0103 (19)
C14	0.083 (3)	0.112 (4)	0.060 (2)	−0.005 (3)	0.017 (2)	−0.032 (3)
C15	0.101 (3)	0.143 (5)	0.059 (2)	0.022 (3)	0.032 (2)	0.038 (3)
C4	0.052 (2)	0.067 (3)	0.054 (2)	−0.0018 (18)	0.0031 (16)	−0.0098 (18)
C12	0.089 (3)	0.073 (3)	0.068 (2)	−0.026 (2)	0.016 (2)	0.007 (2)
C3	0.071 (3)	0.063 (2)	0.075 (3)	−0.011 (2)	0.013 (2)	−0.001 (2)
C11	0.052 (2)	0.074 (2)	0.0495 (18)	0.0027 (19)	−0.0024 (15)	0.0119 (19)

Geometric parameters (Å, º)

O9—C10	1.335 (4)	C16—H16B	0.96
O9—C8	1.462 (4)	C16—H16C	0.96
O10—C10	1.202 (4)	C2—C3	1.506 (5)
O2—C2	1.210 (4)	C14—H14A	0.96
O7—C7	1.351 (3)	C14—H14B	0.96
O7—C11	1.437 (4)	C14—H14C	0.96
N6—C7	1.251 (4)	C15—H15A	0.96
N6—C5	1.456 (4)	C15—H15B	0.96
C7—C8	1.517 (4)	C15—H15C	0.96
C8—C12	1.524 (5)	C4—C3	1.515 (5)
C8—C13	1.553 (5)	C4—H4A	0.97
C10—C5	1.504 (5)	C4—H4B	0.97
C5—C1	1.534 (4)	C12—H12A	0.96
C5—C4	1.549 (5)	C12—H12B	0.96
C1—C2	1.493 (5)	C12—H12C	0.96
C1—H1A	0.97	C3—H3A	0.97
C1—H1B	0.97	C3—H3B	0.97
C13—C16	1.519 (5)	C11—H11A	0.96
C13—C14	1.523 (6)	C11—H11B	0.96
C13—C15	1.538 (6)	C11—H11C	0.96
C16—H16A	0.96
C10—O9—C8	124.8 (3)	O2—C2—C1	125.6 (4)
C7—O7—C11	115.6 (2)	O2—C2—C3	125.2 (4)
C7—N6—C5	120.1 (3)	C1—C2—C3	109.2 (3)
N6—C7—O7	120.9 (3)	C13—C14—H14A	109.5
N6—C7—C8	128.5 (3)	C13—C14—H14B	109.5
O7—C7—C8	110.7 (3)	H14A—C14—H14B	109.5
O9—C8—C7	108.2 (2)	C13—C14—H14C	109.5
O9—C8—C12	103.9 (3)	H14A—C14—H14C	109.5
C7—C8—C12	109.4 (3)	H14B—C14—H14C	109.5
O9—C8—C13	106.7 (2)	C13—C15—H15A	109.5
C7—C8—C13	113.9 (3)	C13—C15—H15B	109.5
C12—C8—C13	114.1 (3)	H15A—C15—H15B	109.5
O10—C10—O9	118.1 (3)	C13—C15—H15C	109.5
O10—C10—C5	122.5 (3)	H15A—C15—H15C	109.5
O9—C10—C5	119.3 (3)	H15B—C15—H15C	109.5
N6—C5—C10	115.9 (3)	C3—C4—C5	104.3 (3)
N6—C5—C1	106.4 (2)	C3—C4—H4A	110.9
C10—C5—C1	109.8 (3)	C5—C4—H4A	110.9
N6—C5—C4	108.4 (3)	C3—C4—H4B	110.9
C10—C5—C4	113.3 (3)	C5—C4—H4B	110.9
C1—C5—C4	101.9 (3)	H4A—C4—H4B	108.9
C2—C1—C5	104.0 (3)	C8—C12—H12A	109.5
C2—C1—H1A	111	C8—C12—H12B	109.5
C5—C1—H1A	111	H12A—C12—H12B	109.5
C2—C1—H1B	111	C8—C12—H12C	109.5
C5—C1—H1B	111	H12A—C12—H12C	109.5
H1A—C1—H1B	109	H12B—C12—H12C	109.5
C16—C13—C14	108.1 (4)	C2—C3—C4	105.2 (3)
C16—C13—C15	108.6 (3)	C2—C3—H3A	110.7
C14—C13—C15	108.4 (3)	C4—C3—H3A	110.7
C16—C13—C8	111.7 (3)	C2—C3—H3B	110.7
C14—C13—C8	110.1 (3)	C4—C3—H3B	110.7
C15—C13—C8	109.9 (4)	H3A—C3—H3B	108.8
C13—C16—H16A	109.5	O7—C11—H11A	109.5
C13—C16—H16B	109.5	O7—C11—H11B	109.5
H16A—C16—H16B	109.5	H11A—C11—H11B	109.5
C13—C16—H16C	109.5	O7—C11—H11C	109.5
H16A—C16—H16C	109.5	H11A—C11—H11C	109.5
H16B—C16—H16C	109.5	H11B—C11—H11C	109.5
C5—N6—C7—O7	177.7 (2)	O10—C10—C5—C4	59.6 (5)
C5—N6—C7—C8	0.0 (5)	O9—C10—C5—C4	−124.7 (3)
C11—O7—C7—N6	−4.4 (4)	N6—C5—C1—C2	−77.4 (3)
C11—O7—C7—C8	173.7 (3)	C10—C5—C1—C2	156.5 (3)
C10—O9—C8—C7	−21.1 (4)	C4—C5—C1—C2	36.1 (3)
C10—O9—C8—C12	−137.3 (3)	O9—C8—C13—C16	176.6 (3)
C10—O9—C8—C13	101.8 (4)	C7—C8—C13—C16	−64.0 (4)
N6—C7—C8—O9	13.9 (5)	C12—C8—C13—C16	62.5 (4)
O7—C7—C8—O9	−163.9 (2)	O9—C8—C13—C14	−63.3 (4)
N6—C7—C8—C12	126.5 (4)	C7—C8—C13—C14	56.0 (4)
O7—C7—C8—C12	−51.4 (4)	C12—C8—C13—C14	−177.5 (3)
N6—C7—C8—C13	−104.6 (4)	O9—C8—C13—C15	56.0 (4)
O7—C7—C8—C13	77.6 (3)	C7—C8—C13—C15	175.3 (3)
C8—O9—C10—O10	−169.3 (3)	C12—C8—C13—C15	−58.2 (4)
C8—O9—C10—C5	14.8 (5)	C5—C1—C2—O2	158.6 (3)
C7—N6—C5—C10	−8.6 (4)	C5—C1—C2—C3	−21.1 (3)
C7—N6—C5—C1	−131.0 (3)	N6—C5—C4—C3	73.6 (3)
C7—N6—C5—C4	120.0 (3)	C10—C5—C4—C3	−156.3 (3)
O10—C10—C5—N6	−174.2 (3)	C1—C5—C4—C3	−38.4 (3)
O9—C10—C5—N6	1.5 (4)	O2—C2—C3—C4	177.2 (3)
O10—C10—C5—C1	−53.6 (5)	C1—C2—C3—C4	−3.1 (4)
O9—C10—C5—C1	122.1 (3)	C5—C4—C3—C2	25.9 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C11—H11A···O2^i	0.96	2.57	3.468 (5)	155
C14—H14C···O10^ii	0.96	2.69	3.589 (4)	156
C12—H12B···O2^iii	0.96	2.72	3.549 (5)	145

Symmetry codes: (i) x+1, y, z; (ii) −x+1, y−1/2, −z+1; (iii) −x+1, y+1/2, −z+2.