The 3,3,5,5[²H₄]-4-methacrylamido-2,2,6,6-tetra­([²H₃]meth­yl)piperidin-1-yloxyl radical

The main features of the crystal structure of the title radical, C₁₃H₇D₁₆N₂O₂, are N—H...O and C—H...O hydrogen bonds, which are responsible for the formation of chains of mol­ecules in the [001] direction.

Key indicators

• Single-crystal X-ray study
• T = 150 K
• Mean [sigma](C-C) = 0.002 Å
• R factor = 0.039
• wR factor = 0.109
• Data-to-parameter ratio = 11.6

checkCIF/PLATON results

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Alert level C
PLAT222_ALERT_3_C Large Non-Solvent    H     Ueq(max)/Ueq(min) ...       3.69 Ratio

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   1 ALERT level C = Check and explain
   0 ALERT level G = General alerts; check

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   0 ALERT type 2 Indicator that the structure model may be wrong or deficient
   1 ALERT type 3 Indicator that the structure quality may be low
   0 ALERT type 4 Improvement, methodology, query or suggestion

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Computing details

Data collection: CrysAlis CCD (Oxford Diffraction, 2004); cell refinement: CrysAlis RED (Oxford Diffraction, 2004); data reduction: CrysAlis RED; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: DIAMOND (Brandenburg & Putz, 2005); software used to prepare material for publication: SHELXL97.

3,3,5,5[²H₄]-4-Methacrylamido-2,2,6,6-tetra([²H₃]methyl)piperidin- 1-yloxyl

Crystal data

C13H7D16N2O2	F(000) = 524
Mr = 255.44	Dx = 1.169 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.7107 Å
Hall symbol: -P 2ybc	Cell parameters from 16217 reflections
a = 12.0838 (5) Å	θ = 1.0–29.5°
b = 11.6346 (6) Å	µ = 0.07 mm^−1
c = 11.5420 (6) Å	T = 150 K
β = 116.522 (4)°	Irregular, yellow
V = 1451.92 (13) Å^3	0.27 × 0.18 × 0.09 mm
Z = 4

Data collection

Oxford Sapphire 2 CCD area-detector diffractometer	2147 reflections with I > 2σ(I)
Radiation source: sealed tube	Rint = 0.038
Graphite monochromator	θmax = 25.4°, θmin = 3.5°
Detector resolution: 8.3438 pixels mm^-1	h = −14→14
ω scans	k = −14→14
16217 measured reflections	l = −13→13
2632 independent reflections

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)] = 0.039	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.109	H atoms treated by a mixture of independent and constrained refinement
S = 1.12	w = 1/[σ^2(Fo^2) + (0.0616P)^2] where P = (Fo^2 + 2Fc^2)/3
2632 reflections	(Δ/σ)max = 0.001
226 parameters	Δρmax = 0.24 e Å^−3
0 restraints	Δρmin = −0.18 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.

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

	x	y	z	Uiso*/Ueq
N1	0.19148 (10)	0.25664 (9)	0.41034 (10)	0.0213 (3)
C2	0.07348 (12)	0.20618 (11)	0.30986 (12)	0.0228 (3)
C3	0.10042 (13)	0.13321 (12)	0.21510 (13)	0.0227 (3)
H3A	0.1152 (13)	0.1852 (12)	0.1556 (13)	0.025 (4)*
H3B	0.0260 (13)	0.0871 (12)	0.1627 (13)	0.025 (4)*
C4	0.21217 (12)	0.05503 (11)	0.27942 (12)	0.0214 (3)
H4A	0.2005 (11)	−0.0022 (11)	0.3360 (11)	0.013 (3)*
C5	0.32586 (13)	0.12779 (12)	0.35805 (13)	0.0234 (3)
H5A	0.3985 (13)	0.0769 (11)	0.4001 (13)	0.021 (3)*
H5B	0.3395 (13)	0.1805 (12)	0.2988 (13)	0.025 (4)*
C6	0.31554 (12)	0.19942 (11)	0.46433 (12)	0.0237 (3)
O7	0.17835 (9)	0.33633 (8)	0.48079 (9)	0.0307 (3)
C8	0.01282 (16)	0.13525 (14)	0.37832 (16)	0.0321 (4)
H8A	0.0608 (14)	0.0651 (13)	0.4244 (14)	0.031 (4)*
H8B	−0.0667 (16)	0.1093 (14)	0.3180 (15)	0.042 (5)*
H8C	0.0018 (14)	0.1826 (13)	0.4454 (15)	0.036 (4)*
C9	−0.01029 (15)	0.30642 (13)	0.23774 (16)	0.0328 (4)
H9A	−0.0859 (16)	0.2743 (13)	0.1631 (16)	0.041 (4)*
H9B	0.0321 (14)	0.3573 (13)	0.2027 (14)	0.033 (4)*
H9C	−0.0302 (14)	0.3522 (13)	0.2956 (15)	0.036 (4)*
N10	0.22804 (11)	−0.01080 (9)	0.17994 (11)	0.0259 (3)
H10	0.2151 (14)	0.0225 (13)	0.1112 (15)	0.036 (4)*
C11	0.28168 (11)	−0.11508 (11)	0.20321 (12)	0.0195 (3)
O12	0.31476 (9)	−0.16342 (8)	0.30842 (9)	0.0280 (3)
C13	0.29670 (12)	−0.17229 (11)	0.09358 (12)	0.0204 (3)
C14	0.28749 (13)	−0.11195 (12)	−0.01252 (13)	0.0283 (3)
H14A	0.2990	−0.1493	−0.0776	0.042*
H14B	0.2698	−0.0337	−0.0194	0.042*
C15	0.32418 (15)	−0.29466 (12)	0.10982 (14)	0.0321 (4)
H15A	0.3284	−0.3241	0.0342	0.048*
H15B	0.2602	−0.3340	0.1218	0.048*
H15C	0.4021	−0.3066	0.1843	0.048*
C16	0.33133 (17)	0.12413 (14)	0.57972 (15)	0.0339 (4)
H16A	0.2732 (14)	0.0562 (13)	0.5517 (14)	0.035 (4)*
H16B	0.4186 (17)	0.0988 (14)	0.6224 (16)	0.046 (5)*
H16C	0.3134 (16)	0.1669 (14)	0.6408 (16)	0.046 (5)*
C17	0.41298 (15)	0.29402 (14)	0.50904 (17)	0.0338 (4)
H17A	0.4935 (16)	0.2575 (13)	0.5372 (15)	0.039 (4)*
H17B	0.3977 (13)	0.3451 (12)	0.4338 (14)	0.027 (4)*
H17C	0.4050 (14)	0.3405 (13)	0.5777 (15)	0.035 (4)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N1	0.0273 (6)	0.0161 (6)	0.0237 (6)	−0.0014 (4)	0.0141 (5)	−0.0053 (4)
C2	0.0232 (7)	0.0204 (7)	0.0254 (7)	−0.0018 (5)	0.0115 (6)	−0.0046 (5)
C3	0.0279 (8)	0.0194 (7)	0.0207 (7)	0.0008 (6)	0.0109 (6)	−0.0019 (6)
C4	0.0332 (8)	0.0167 (7)	0.0187 (7)	0.0031 (6)	0.0156 (6)	0.0008 (5)
C5	0.0276 (8)	0.0210 (7)	0.0245 (7)	0.0051 (6)	0.0143 (6)	0.0024 (6)
C6	0.0255 (8)	0.0205 (7)	0.0229 (7)	0.0020 (5)	0.0087 (6)	−0.0017 (5)
O7	0.0372 (6)	0.0235 (5)	0.0379 (6)	−0.0041 (4)	0.0225 (5)	−0.0149 (4)
C8	0.0350 (9)	0.0320 (9)	0.0376 (9)	−0.0099 (7)	0.0235 (8)	−0.0108 (7)
C9	0.0305 (9)	0.0278 (8)	0.0376 (9)	0.0060 (7)	0.0129 (8)	−0.0053 (7)
N10	0.0460 (8)	0.0176 (6)	0.0190 (6)	0.0079 (5)	0.0189 (5)	0.0036 (5)
C11	0.0217 (7)	0.0169 (7)	0.0211 (7)	−0.0002 (5)	0.0108 (6)	0.0003 (5)
O12	0.0402 (6)	0.0248 (5)	0.0224 (5)	0.0106 (4)	0.0169 (4)	0.0056 (4)
C13	0.0218 (7)	0.0190 (7)	0.0213 (7)	−0.0002 (5)	0.0105 (6)	−0.0025 (5)
C14	0.0401 (9)	0.0245 (7)	0.0255 (7)	0.0043 (6)	0.0193 (7)	−0.0037 (6)
C15	0.0434 (9)	0.0260 (8)	0.0316 (8)	0.0065 (6)	0.0210 (7)	−0.0021 (6)
C16	0.0496 (11)	0.0277 (8)	0.0228 (8)	0.0039 (8)	0.0148 (8)	−0.0011 (6)
C17	0.0266 (9)	0.0290 (8)	0.0402 (9)	−0.0013 (6)	0.0098 (7)	−0.0051 (7)

Geometric parameters (Å, º)

N1—O7	1.289 (1)	C9—H9A	1.007 (17)
N1—C2	1.499 (2)	C9—H9B	0.981 (16)
N1—C6	1.498 (2)	C9—H9C	0.965 (16)
C2—C9	1.525 (2)	N10—C11	1.345 (2)
C2—C3	1.530 (2)	N10—H10	0.833 (16)
C2—C8	1.536 (2)	C11—O12	1.232 (1)
C3—C4	1.519 (2)	C11—C13	1.511 (2)
C3—H3A	0.989 (14)	C13—C14	1.372 (2)
C3—H3B	0.988 (14)	C13—C15	1.455 (1)
C4—N10	1.462 (2)	C14—H14A	0.9300
C4—C5	1.521 (2)	C14—H14B	0.9300
C4—H4A	0.986 (12)	C15—H15A	0.9600
C5—C6	1.533 (2)	C15—H15B	0.9600
C5—H5A	0.989 (19)	C15—H15C	0.9600
C5—H5B	0.986 (14)	C16—H16A	1.010 (16)
C6—C17	1.524 (2)	C16—H16B	0.989 (18)
C6—C16	1.533 (2)	C16—H16C	0.963 (17)
C8—H8A	1.005 (15)	C17—H17A	0.975 (17)
C8—H8B	0.949 (17)	C17—H17B	0.999 (14)
C8—H8C	1.006 (16)	C17—H17C	0.999 (16)
O7—N1—C2	115.3 (1)	H8B—C8—H8C	107.5 (13)
O7—N1—C6	116.1 (1)	C2—C9—H9A	108.1 (9)
C2—N1—C6	125.3 (1)	C2—C9—H9B	110.2 (9)
N1—C2—C9	107.0 (1)	H9A—C9—H9B	108.3 (13)
N1—C2—C3	109.8 (1)	C2—C9—H9C	110.8 (9)
C9—C2—C3	109.6 (1)	H9A—C9—H9C	112.6 (13)
N1—C2—C8	108.7 (1)	H9B—C9—H9C	106.9 (12)
C9—C2—C8	109.8 (1)	C11—N10—C4	122.4 (1)
C3—C2—C8	111.9 (1)	C11—N10—H10	118.6 (11)
C4—C3—C2	114.2 (1)	C4—N10—H10	118.0 (11)
C4—C3—H3A	108.0 (8)	O12—C11—N10	121.6 (1)
C2—C3—H3A	108.6 (8)	O12—C11—C13	121.1 (1)
C4—C3—H3B	110.0 (8)	N10—C11—C13	117.2 (1)
C2—C3—H3B	108.2 (8)	C14—C13—C15	122.6 (1)
H3A—C3—H3B	107.7 (11)	C14—C13—C11	122.0 (1)
N10—C4—C3	109.2 (1)	C15—C13—C11	115.4 (1)
N10—C4—C5	111.1 (1)	C13—C14—H14A	120.0
C3—C4—C5	109.1 (1)	C13—C14—H14B	120.0
N10—C4—H4A	105.9 (7)	H14A—C14—H14B	120.0
C3—C4—H4A	111.7 (7)	C13—C15—H15A	109.5
C5—C4—H4A	109.8 (7)	C13—C15—H15B	109.5
C4—C5—C6	113.91 (11)	H15A—C15—H15B	109.5
C4—C5—H5A	109.1 (8)	C13—C15—H15C	109.5
C6—C5—H5A	107.8 (8)	H15A—C15—H15C	109.5
C4—C5—H5B	108.6 (8)	H15B—C15—H15C	109.5
C6—C5—H5B	108.4 (8)	C6—C16—H16A	111.7 (8)
H5A—C5—H5B	109.0 (11)	C6—C16—H16B	107.1 (9)
N1—C6—C17	107.4 (1)	H16A—C16—H16B	111.2 (13)
N1—C6—C5	109.4 (1)	C6—C16—H16C	111.1 (10)
C17—C6—C5	109.7 (1)	H16A—C16—H16C	106.7 (13)
N1—C6—C16	109.2 (1)	H16B—C16—H16C	109.1 (14)
C17—C6—C16	109.9 (1)	C6—C17—H17A	107.7 (9)
C5—C6—C16	111.2 (1)	C6—C17—H17B	108.7 (8)
C2—C8—H8A	114.4 (8)	H17A—C17—H17B	108.5 (12)
C2—C8—H8B	110.6 (10)	C6—C17—H17C	109.0 (9)
H8A—C8—H8B	106.6 (13)	H17A—C17—H17C	114.0 (12)
C2—C8—H8C	111.1 (9)	H17B—C17—H17C	108.8 (11)
H8A—C8—H8C	106.3 (12)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3A···O7^i	0.99 (1)	2.47 (2)	3.256 (2)	136 (1)
N10—H10···O7^i	0.83 (2)	2.14 (2)	2.921 (1)	157 (1)
C14—H14B···O7^i	0.93	2.55	3.455 (1)	165
C17—H17A···O12^ii	0.97 (2)	2.46 (1)	3.373 (2)	156 (1)
C15—H15A···O12^iii	0.96	2.54	3.464 (2)	161
C14—H14A···O12^iii	0.93	2.59	3.438 (2)	151

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