TEMPO radicals showing magnetic interactions. II. 4-(Benzylideneamino)-TEMPO and related compounds

Iwasaki, F.; Yoshikawa, J.H.; Yamamoto, H.; Takada, K.; Kan-nari, E.; Yasui, M.; Ishida, T.; Nogami, T.

doi:10.1107/S0108768199007326

TEMPO radicals showing magnetic interactions. II. 4-(Benzylideneamino)-TEMPO and related compounds

F. Iwasaki, J. H. Yoshikawa, H. Yamamoto, K. Takada, E. Kan-nari, M. Yasui, T. Ishida and T. Nogami

X-ray crystal structure analyses were performed on 4-(Ar-methyleneamino)-TEMPO radicals at room temperature (TEMPO = 2,2,6,6-tetramethylpiperidyl-1-oxyl): Ar = Ph [4-(benzylideneamino)-2,2,6,6-tetramethylpiperidyl-1-oxyl], 4-MeS-Ph [2,2,6,6-tetramethyl-4-(4-methylthiobenzylideneamino)piperidyl-1-oxyl], 4-Me-Ph [4-(4-methylbenzylideneamino)-2,2,6,6-tetramethylpiperidyl-1-oxyl], 4-PhO-Ph [2,2,6,6-tetramethyl-4-(4-phenoxybenzylideneamino)piperidyl-1-oxyl], 4-MeSO $_{2}$ -Ph [2,2,6,6-tetramethyl-4-(4-methylsulfonylbenzylideneamino)piperidyl-1-oxyl], 3-Py [2,2,6,6-tetramethyl-4-(3-pyridylmethylideneamino)piperidyl-1-oxyl] and 2-Naph [2,2,6,6-tetramethyl-4-(2-naphthylideneamino)piperidyl-1-oxyl]. Structures of Ph and 4-Me-Ph derivatives were also determined at 100 K. Some of these crystals have been revealed to show intermolecular ferromagnetic interactions at an extremely low temperature. Structural features of crystals of Ph, 4-MeS-Ph and 3-Py derivatives, which show ferromagnetic interactions, are very similar to each other. In these crystals, O atoms are arranged to form a sheet. The ferromagnetic interactions are considered to be transferred through O

H van der Waals' interactions of the $\beta$ -H atoms of the neighboring TEMPO rings within the sheet. Between O

O sheets, the aryl groups are arranged in a herringbone manner. The crystal structure of the 4-Me-Ph derivative, which shows an antiferromagnetic interaction, is also pseudo-isostructural with those of Ph, 4-MeS-Ph and 3-Py derivatives, while the arrangement of the aryl groups is different. The packing mode of the crystals of the 4-MeSO $_{2}$ -Ph derivative, of which the Weiss constant $\theta$ is nearly zero, is very different from those of the other derivatives showing magnetic interactions. The fact that the crystal structure of the paramagnetic 4-MeSO $_{2}$ -Ph derivative does not show the O

O sheet structure accompanying the O

$\beta$ -H interactions indicates that the intermolecular ferromagnetic interactions through $\beta$ -H atoms within the O

O sheet are important for these TEMPO radical crystals.

Keywords: TEMPO radicals; Ferromagnetic interactions.

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Supporting information

	Crystallographic Information File (CIF) Contains datablocks 8a, 8b, 9, 10, 11a, 11b, 12, 13, 14, text
	Structure factor file (CIF format) Contains datablock 8a
	Structure factor file (CIF format) Contains datablock 8b
	Structure factor file (CIF format) Contains datablock 9
	Structure factor file (CIF format) Contains datablock 10
	Structure factor file (CIF format) Contains datablock 11a
	Structure factor file (CIF format) Contains datablock 11b
	Structure factor file (CIF format) Contains datablock 12
	Structure factor file (CIF format) Contains datablock 13
	Structure factor file (CIF format) Contains datablock 14

CCDC references: 138573; 138574; 138575; 138576; 138577; 138578; 138579; 138580; 138581

Computing details top

Data collection: AFC (Rigaku Co., 1994) for (8a), (8b), (9), (11a), (11b), (14); AFC (Rigaku Co., 1990) for (10), (12); AFC (Rigaku Co., 1978) for (13). Cell refinement: AFC (Rigaku Co., 1994) for (8a), (8b), (9), (11a), (11b), (14); AFC (Rigaku Co., 1990) for (10), (12); AFC (Rigaku Co., 1978) for (13). For all compounds, data reduction: TEXSAN (MSC, 1992). Program(s) used to solve structure: SAPI91 (Fan, 1991) for (8a), (9), (11a), (11b), (12), (13), (14); SIR88 (Burla, et al. 1989) for (8b), (10). Program(s) used to refine structure: SHELXL97 (Sheldrick, 1997) for (8a), (8b), (9), (10), (11a), (12), (13), (14); SHELXS97 (Sheldrick, 1997) for (11b). For all compounds, molecular graphics: ORTEP II (Johnson, 1976). Software used to prepare material for publication: SHELXL97 (Sheldrick, 1997) for (8a), (8b), (9), (10), (11a), (12), (13), (14); SHELXS97 (Sheldrick, 1997) for (11b).

(8a) 4-benzylideneamino-2,2,6,6-tetramethylpiperidin-1-oxyl top

Crystal data top

C₁₆H₂₃N₂O	D_x = 1.127 Mg m⁻³
M_r = 259.37	Melting point: not measured K
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
a = 12.684 (7) Å	Cell parameters from 25 reflections
b = 11.740 (2) Å	θ = 14.8–17.4°
c = 11.024 (3) Å	µ = 0.07 mm⁻¹
β = 111.40 (4)°	T = 296 K
V = 1528.3 (9) Å³	Prism, orange
Z = 4	0.50 × 0.40 × 0.20 mm
F(000) = 564.00

Data collection top

Rigaku AFC7R diffractometer	R_int = 0.016
Radiation source: Rigaku rotating anode	θ_max = 27.5°, θ_min = 2.6°
Graphite monochromator	h = −16→15
ω–2θ scans	k = −15→0
3712 measured reflections	l = 0→14
3528 independent reflections	3 standard reflections every 150 reflections
2110 reflections with I > 2σ(I)	intensity decay: 7.2%

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: difmap and geom
R[F² > 2σ(F²)] = 0.050	All H-atom parameters refined
wR(F²) = 0.147	Calculated w = 1/[σ²(F_o²) + (0.0684P)² + 0.1077P] where P = (F_o² + 2F_c²)/3
S = 1.01	(Δ/σ)_max = 0.001
3528 reflections	Δρ_max = 0.17 e Å⁻³
265 parameters	Δρ_min = −0.17 e Å⁻³
0 restraints	Extinction correction: SHELXL-97 (Sheldrick, 1997), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.021 (3)

Special details top

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 (Å²) top

	x	y	z	U_iso*/U_eq
O1	0.45509 (13)	0.79615 (11)	0.29802 (15)	0.0725 (4)
N1	0.40152 (12)	0.71365 (12)	0.22545 (13)	0.0487 (4)
N2	0.22404 (13)	0.43611 (13)	−0.00187 (13)	0.0541 (4)
C2	0.47296 (14)	0.62041 (15)	0.20449 (16)	0.0519 (5)
C3	0.39983 (15)	0.54071 (17)	0.09712 (17)	0.0512 (5)
C4	0.28888 (15)	0.50776 (14)	0.10926 (17)	0.0492 (4)
C5	0.22180 (15)	0.61558 (16)	0.10554 (18)	0.0501 (4)
C6	0.28115 (15)	0.70026 (15)	0.21364 (16)	0.0500 (4)
C7	0.21319 (15)	0.33288 (15)	0.02044 (18)	0.0514 (4)
C11	0.14956 (13)	0.25068 (15)	−0.08102 (17)	0.0504 (4)
C12	0.10021 (16)	0.28265 (18)	−0.21091 (18)	0.0568 (5)
C13	0.03793 (17)	0.2045 (2)	−0.3032 (2)	0.0665 (6)
C14	0.02475 (18)	0.0948 (2)	−0.2672 (2)	0.0690 (6)
C15	0.07377 (18)	0.06236 (18)	−0.1395 (3)	0.0716 (6)
C16	0.13617 (17)	0.13984 (17)	−0.0463 (2)	0.0639 (5)
C21	0.5296 (2)	0.5574 (2)	0.3338 (2)	0.0764 (7)
C22	0.5621 (2)	0.6752 (3)	0.1607 (3)	0.0803 (8)
C61	0.2775 (2)	0.6621 (2)	0.3451 (2)	0.0705 (6)
C62	0.2248 (2)	0.8166 (2)	0.1788 (3)	0.0712 (6)
H4	0.3008 (14)	0.4687 (15)	0.1878 (18)	0.049 (5)*
H7	0.2444 (16)	0.2998 (16)	0.109 (2)	0.063 (5)*
H12	0.1109 (15)	0.3629 (17)	−0.2339 (17)	0.057 (5)*
H13	0.005 (2)	0.231 (2)	−0.394 (3)	0.094 (8)*
H14	−0.0193 (19)	0.038 (2)	−0.327 (2)	0.085 (7)*
H15	0.069 (2)	−0.018 (2)	−0.109 (2)	0.092 (7)*
H16	0.1742 (19)	0.116 (2)	0.040 (2)	0.084 (7)*
H21	0.472 (2)	0.518 (2)	0.358 (2)	0.089 (8)*
H22	0.582 (2)	0.505 (2)	0.330 (3)	0.097 (8)*
H23	0.571 (2)	0.612 (2)	0.400 (3)	0.098 (8)*
H24	0.527 (2)	0.717 (2)	0.080 (3)	0.113 (10)*
H25	0.611 (2)	0.614 (3)	0.152 (3)	0.112 (9)*
H26	0.607 (2)	0.726 (2)	0.229 (3)	0.099 (8)*
H31	0.3813 (14)	0.5826 (15)	0.0117 (18)	0.052 (5)*
H32	0.4418 (17)	0.4737 (18)	0.101 (2)	0.068 (6)*
H51	0.1479 (15)	0.5976 (16)	0.1106 (16)	0.053 (5)*
H52	0.2068 (15)	0.6507 (16)	0.0179 (19)	0.058 (5)*
H61	0.3057 (17)	0.5859 (19)	0.3645 (19)	0.064 (6)*
H62	0.200 (2)	0.663 (2)	0.344 (2)	0.104 (9)*
H63	0.328 (2)	0.712 (2)	0.417 (2)	0.091 (8)*
H64	0.145 (2)	0.804 (2)	0.166 (3)	0.103 (9)*
H65	0.258 (2)	0.872 (2)	0.250 (2)	0.089 (7)*
H66	0.238 (2)	0.848 (2)	0.099 (3)	0.095 (8)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0789 (9)	0.0533 (8)	0.0814 (10)	−0.0198 (7)	0.0246 (8)	−0.0270 (7)
N1	0.0560 (8)	0.0411 (8)	0.0464 (8)	−0.0066 (6)	0.0157 (6)	−0.0083 (6)
N2	0.0654 (10)	0.0455 (9)	0.0412 (8)	−0.0070 (7)	0.0072 (7)	−0.0058 (6)
C2	0.0479 (9)	0.0555 (11)	0.0454 (9)	0.0023 (8)	0.0090 (8)	−0.0108 (8)
C3	0.0534 (10)	0.0489 (10)	0.0437 (9)	0.0076 (8)	0.0088 (8)	−0.0091 (8)
C4	0.0619 (11)	0.0404 (9)	0.0359 (8)	−0.0057 (8)	0.0067 (8)	−0.0022 (7)
C5	0.0469 (10)	0.0541 (11)	0.0478 (10)	−0.0044 (8)	0.0154 (8)	−0.0042 (8)
C6	0.0555 (10)	0.0479 (10)	0.0498 (9)	−0.0037 (8)	0.0231 (8)	−0.0075 (8)
C7	0.0522 (10)	0.0450 (10)	0.0468 (10)	0.0012 (8)	0.0059 (8)	−0.0023 (8)
C11	0.0444 (9)	0.0452 (9)	0.0535 (10)	0.0037 (7)	0.0083 (8)	−0.0093 (8)
C12	0.0559 (10)	0.0545 (12)	0.0544 (11)	−0.0047 (9)	0.0133 (9)	−0.0097 (9)
C13	0.0575 (12)	0.0792 (16)	0.0540 (12)	−0.0071 (10)	0.0100 (9)	−0.0193 (11)
C14	0.0573 (12)	0.0640 (13)	0.0788 (15)	−0.0083 (10)	0.0167 (11)	−0.0324 (12)
C15	0.0667 (13)	0.0461 (12)	0.0907 (17)	−0.0018 (10)	0.0154 (12)	−0.0152 (11)
C16	0.0631 (12)	0.0464 (11)	0.0674 (13)	0.0025 (9)	0.0062 (10)	−0.0046 (10)
C21	0.0735 (15)	0.0752 (16)	0.0553 (12)	0.0171 (14)	−0.0066 (12)	−0.0110 (12)
C22	0.0553 (12)	0.108 (2)	0.0783 (17)	−0.0193 (14)	0.0246 (12)	−0.0312 (16)
C61	0.0900 (17)	0.0726 (16)	0.0584 (13)	−0.0148 (14)	0.0383 (12)	−0.0105 (12)
C62	0.0776 (16)	0.0590 (13)	0.0809 (16)	0.0113 (11)	0.0336 (13)	−0.0098 (12)

Geometric parameters (Å, º) top

O1—N1	1.2818 (18)	C12—C13	1.384 (3)
N1—C2	1.492 (2)	C12—H12	0.997 (19)
N1—C6	1.492 (2)	C13—C14	1.376 (3)
N2—C4	1.466 (2)	C13—H13	0.98 (3)
N2—C7	1.254 (2)	C14—C15	1.369 (3)
C2—C22	1.525 (3)	C14—H14	0.96 (2)
C2—C3	1.528 (2)	C15—C16	1.384 (3)
C2—C21	1.533 (3)	C15—H15	1.01 (3)
C3—C4	1.512 (3)	C16—H16	0.94 (2)
C3—H31	1.011 (18)	C21—H21	0.98 (3)
C3—H32	0.94 (2)	C21—H22	0.92 (3)
C4—C5	1.517 (3)	C21—H23	0.97 (3)
C4—H4	0.942 (18)	C22—H24	0.97 (3)
C5—C6	1.523 (2)	C22—H25	0.97 (3)
C5—H51	0.982 (18)	C22—H26	0.97 (3)
C5—H52	1.003 (19)	C61—H61	0.96 (2)
C6—C62	1.524 (3)	C61—H62	0.98 (3)
C6—C61	1.533 (3)	C61—H63	1.00 (3)
C7—C11	1.475 (2)	C62—H64	0.98 (3)
C7—H7	0.99 (2)	C62—H65	0.99 (2)
C11—C16	1.384 (3)	C62—H66	1.02 (3)
C11—C12	1.389 (3)

O1···O1ⁱ	5.6173 (16)	O1···H32ⁱⁱ	2.50 (2)
O1···O1ⁱⁱ	6.1447 (13)	O1···H22ⁱⁱ	2.78 (3)
O1···C3ⁱⁱ	3.378 (3)	O1···H24ⁱ	2.91 (3)
O1···C21ⁱⁱ	3.429 (3)	O1···H31ⁱ	3.172 (18)

O1—N1—C2	115.94 (14)	C13—C12—C11	120.0 (2)
O1—N1—C6	115.24 (13)	C13—C12—H12	122.2 (11)
C2—N1—C6	124.68 (13)	C11—C12—H12	117.7 (10)
C7—N2—C4	117.31 (15)	C14—C13—C12	120.4 (2)
N1—C2—C22	107.58 (18)	C14—C13—H13	122.4 (15)
N1—C2—C3	109.75 (14)	C12—C13—H13	117.3 (15)
C22—C2—C3	108.88 (17)	C15—C14—C13	120.0 (2)
N1—C2—C21	108.39 (16)	C15—C14—H14	116.2 (14)
C22—C2—C21	110.4 (2)	C13—C14—H14	123.8 (14)
C3—C2—C21	111.77 (17)	C14—C15—C16	120.2 (2)
C4—C3—C2	114.18 (15)	C14—C15—H15	122.7 (14)
C4—C3—H31	107.4 (10)	C16—C15—H15	117.0 (14)
C2—C3—H31	107.0 (10)	C11—C16—C15	120.5 (2)
C4—C3—H32	108.2 (12)	C11—C16—H16	119.6 (15)
C2—C3—H32	107.8 (12)	C15—C16—H16	119.8 (15)
H31—C3—H32	112.3 (16)	C2—C21—H21	109.5 (14)
N2—C4—C3	109.22 (14)	C2—C21—H22	112.3 (17)
N2—C4—C5	108.54 (14)	H21—C21—H22	109 (2)
C3—C4—C5	108.36 (15)	C2—C21—H23	108.5 (15)
N2—C4—H4	110.0 (10)	H21—C21—H23	111 (2)
C3—C4—H4	111.3 (10)	H22—C21—H23	107 (2)
C5—C4—H4	109.3 (10)	C2—C22—H24	110.8 (17)
C4—C5—C6	114.28 (15)	C2—C22—H25	106.7 (17)
C4—C5—H51	110.9 (11)	H24—C22—H25	112 (2)
C6—C5—H51	107.8 (10)	C2—C22—H26	107.6 (15)
C4—C5—H52	106.1 (11)	H24—C22—H26	110 (2)
C6—C5—H52	110.6 (11)	H25—C22—H26	109 (2)
H51—C5—H52	107.0 (15)	C6—C61—H61	110.3 (12)
N1—C6—C5	109.56 (14)	C6—C61—H62	111.1 (15)
N1—C6—C62	107.37 (16)	H61—C61—H62	108 (2)
C5—C6—C62	109.58 (17)	C6—C61—H63	110.3 (14)
N1—C6—C61	109.31 (17)	H61—C61—H63	106.9 (18)
C5—C6—C61	111.84 (17)	H62—C61—H63	110 (2)
C62—C6—C61	109.09 (18)	C6—C62—H64	105.7 (15)
N2—C7—C11	123.53 (17)	C6—C62—H65	111.7 (13)
N2—C7—H7	122.7 (11)	H64—C62—H65	109 (2)
C11—C7—H7	113.7 (11)	C6—C62—H66	109.4 (14)
C16—C11—C12	118.97 (17)	H64—C62—H66	114 (2)
C16—C11—C7	119.61 (17)	H65—C62—H66	106.8 (19)
C12—C11—C7	121.41 (17)

O1—N1—C2—C22	−51.1 (2)	C2—N1—C6—C5	−34.9 (2)
C6—N1—C2—C22	152.96 (17)	C2—N1—C6—C62	−153.78 (16)
O1—N1—C2—C3	−169.38 (15)	O1—N1—C6—C61	−68.1 (2)
C6—N1—C2—C3	34.6 (2)	C2—N1—C6—C61	88.02 (19)
O1—N1—C2—C21	68.3 (2)	C4—C5—C6—C62	163.45 (17)
C6—N1—C2—C21	−87.7 (2)	C4—C5—C6—C61	−75.5 (2)
N1—C2—C3—C4	−45.5 (2)	C4—N2—C7—C11	179.41 (16)
C22—C2—C3—C4	−163.0 (2)	N2—C7—C11—C16	−176.11 (19)
C21—C2—C3—C4	74.8 (2)	N2—C7—C11—C12	2.4 (3)
C7—N2—C4—C3	109.92 (19)	C16—C11—C12—C13	0.6 (3)
C7—N2—C4—C5	−132.12 (18)	C7—C11—C12—C13	−177.91 (17)
C4—C5—C6—N1	45.9 (2)	C11—C12—C13—C14	−0.2 (3)
C2—C3—C4—C5	59.2 (2)	C12—C13—C14—C15	−0.3 (3)
C3—C4—C5—C6	−59.6 (2)	C13—C14—C15—C16	0.3 (3)
C2—C3—C4—N2	177.30 (15)	C12—C11—C16—C15	−0.5 (3)
N2—C4—C5—C6	−178.13 (15)	C7—C11—C16—C15	177.99 (19)
O1—N1—C6—C5	169.01 (15)	C14—C15—C16—C11	0.1 (3)
O1—N1—C6—C62	50.1 (2)

Symmetry codes: (i) x, −y+3/2, z+1/2; (ii) −x+1, y+1/2, −z+1/2.

(8b) 4-benzylideneamino-2,2,6,6-tetramethylpiperidin-1-oxyl top

Crystal data top

C₁₆H₂₃N₂O	D_x = 1.165 Mg m⁻³
M_r = 259.37	Melting point: not measured K
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
a = 12.5774 (14) Å	Cell parameters from 25 reflections
b = 11.6228 (16) Å	θ = 12.9–15.2°
c = 10.8229 (17) Å	µ = 0.07 mm⁻¹
β = 110.853 (9)°	T = 100 K
V = 1478.5 (3) Å³	Prism, orange
Z = 4	0.35 × 0.35 × 0.20 mm
F(000) = 564

Data collection top

Rigaku AFC7R diffractometer	R_int = 0.023
Radiation source: Rigaku rotating anode	θ_max = 27.5°, θ_min = 2.5°
Graphite monochromator	h = 0→16
ω–2θ scans	k = −15→15
7062 measured reflections	l = −14→13
3383 independent reflections	3 standard reflections every 150 reflections
2731 reflections with I > 2σ(I)	intensity decay: 0.5%

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.036	Hydrogen site location: difference Fourier map
wR(F²) = 0.099	All H-atom parameters refined
S = 1.02	Calculated w = 1/[σ²(F_o²) + (0.0459P)² + 0.3544P] where P = (F_o² + 2F_c²)/3
3383 reflections	(Δ/σ)_max = 0.001
264 parameters	Δρ_max = 0.27 e Å⁻³
0 restraints	Δρ_min = −0.18 e Å⁻³

Special details top

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
O1	0.45309 (7)	0.80100 (7)	0.29639 (8)	0.0272 (2)
N1	0.39996 (8)	0.71694 (8)	0.22244 (9)	0.0192 (2)
N2	0.22530 (8)	0.43205 (8)	−0.00384 (9)	0.0217 (2)
C2	0.47332 (9)	0.62293 (9)	0.20138 (10)	0.0205 (2)
C3	0.40119 (9)	0.54054 (10)	0.09327 (10)	0.0202 (2)
C4	0.28946 (9)	0.50573 (9)	0.10809 (10)	0.0199 (2)
C5	0.22008 (9)	0.61410 (9)	0.10334 (11)	0.0200 (2)
C6	0.27928 (9)	0.70112 (9)	0.21241 (10)	0.0197 (2)
C7	0.21226 (9)	0.32793 (9)	0.02204 (10)	0.0203 (2)
C11	0.14787 (9)	0.24433 (9)	−0.08008 (10)	0.0200 (2)
C12	0.09898 (9)	0.27602 (10)	−0.21320 (11)	0.0224 (2)
C13	0.03567 (10)	0.19668 (10)	−0.30631 (11)	0.0245 (2)
C14	0.02034 (9)	0.08542 (10)	−0.26863 (12)	0.0252 (2)
C15	0.06954 (10)	0.05302 (10)	−0.13676 (12)	0.0258 (2)
C16	0.13327 (9)	0.13204 (10)	−0.04302 (12)	0.0238 (2)
C21	0.53210 (11)	0.56092 (11)	0.33356 (12)	0.0283 (3)
C22	0.56274 (10)	0.67946 (12)	0.15513 (13)	0.0296 (3)
C61	0.27685 (11)	0.66206 (11)	0.34716 (11)	0.0261 (2)
C62	0.22004 (11)	0.81800 (10)	0.17703 (12)	0.0265 (3)
H4	0.3052 (10)	0.4636 (11)	0.1932 (12)	0.019 (3)*
H7	0.2440 (11)	0.2955 (11)	0.1137 (13)	0.022 (3)*
H12	0.1098 (12)	0.3537 (13)	−0.2398 (14)	0.032 (4)*
H13	0.0043 (12)	0.2189 (12)	−0.3977 (14)	0.031 (4)*
H14	−0.0258 (13)	0.0283 (13)	−0.3314 (14)	0.037 (4)*
H15	0.0595 (12)	−0.0253 (12)	−0.1099 (14)	0.028 (3)*
H16	0.1677 (12)	0.1098 (13)	0.0481 (14)	0.033 (4)*
H21	0.4754 (13)	0.5213 (13)	0.3662 (15)	0.037 (4)*
H22	0.5852 (13)	0.5041 (14)	0.3240 (15)	0.039 (4)*
H23	0.5723 (13)	0.6179 (13)	0.3999 (15)	0.037 (4)*
H24	0.5270 (13)	0.7189 (13)	0.0676 (15)	0.036 (4)*
H25	0.6155 (13)	0.6195 (13)	0.1459 (15)	0.037 (4)*
H26	0.6048 (14)	0.7397 (14)	0.2184 (16)	0.046 (4)*
H31	0.3833 (11)	0.5781 (11)	0.0035 (13)	0.022 (3)*
H32	0.4467 (12)	0.4718 (13)	0.0945 (14)	0.031 (4)*
H51	0.1445 (11)	0.5940 (12)	0.1095 (13)	0.025 (3)*
H52	0.2051 (11)	0.6517 (12)	0.0143 (13)	0.027 (3)*
H61	0.3023 (12)	0.5813 (13)	0.3674 (14)	0.033 (4)*
H62	0.1970 (13)	0.6676 (13)	0.3462 (14)	0.037 (4)*
H63	0.3271 (12)	0.7111 (12)	0.4193 (14)	0.029 (4)*
H64	0.1359 (13)	0.8067 (12)	0.1584 (14)	0.033 (4)*
H65	0.2509 (13)	0.8741 (13)	0.2497 (15)	0.036 (4)*
H66	0.2311 (12)	0.8528 (13)	0.0962 (15)	0.034 (4)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0310 (4)	0.0203 (4)	0.0280 (4)	−0.0068 (3)	0.0076 (3)	−0.0086 (3)
N1	0.0220 (4)	0.0162 (4)	0.0183 (4)	−0.0018 (3)	0.0059 (3)	−0.0029 (3)
N2	0.0238 (5)	0.0203 (5)	0.0184 (4)	−0.0018 (4)	0.0042 (4)	−0.0022 (3)
C2	0.0189 (5)	0.0215 (5)	0.0190 (5)	0.0013 (4)	0.0041 (4)	−0.0040 (4)
C3	0.0210 (5)	0.0196 (5)	0.0176 (5)	0.0020 (4)	0.0038 (4)	−0.0034 (4)
C4	0.0242 (5)	0.0172 (5)	0.0153 (5)	−0.0021 (4)	0.0034 (4)	−0.0019 (4)
C5	0.0194 (5)	0.0206 (5)	0.0194 (5)	−0.0013 (4)	0.0062 (4)	−0.0015 (4)
C6	0.0217 (5)	0.0190 (5)	0.0195 (5)	−0.0001 (4)	0.0088 (4)	−0.0016 (4)
C7	0.0202 (5)	0.0198 (5)	0.0186 (5)	0.0006 (4)	0.0039 (4)	−0.0011 (4)
C11	0.0183 (5)	0.0188 (5)	0.0211 (5)	0.0008 (4)	0.0048 (4)	−0.0030 (4)
C12	0.0221 (5)	0.0222 (6)	0.0220 (5)	−0.0009 (4)	0.0068 (4)	−0.0019 (4)
C13	0.0221 (5)	0.0292 (6)	0.0207 (5)	−0.0018 (4)	0.0058 (4)	−0.0051 (4)
C14	0.0210 (5)	0.0250 (6)	0.0281 (6)	−0.0020 (4)	0.0069 (4)	−0.0102 (5)
C15	0.0245 (5)	0.0178 (5)	0.0333 (6)	−0.0001 (4)	0.0082 (5)	−0.0032 (5)
C16	0.0235 (5)	0.0198 (5)	0.0245 (5)	0.0017 (4)	0.0040 (4)	−0.0007 (4)
C21	0.0287 (6)	0.0283 (6)	0.0202 (5)	0.0058 (5)	−0.0007 (4)	−0.0034 (5)
C22	0.0218 (5)	0.0395 (7)	0.0278 (6)	−0.0060 (5)	0.0090 (5)	−0.0095 (5)
C61	0.0325 (6)	0.0276 (6)	0.0206 (5)	−0.0032 (5)	0.0126 (5)	−0.0023 (5)
C62	0.0294 (6)	0.0234 (6)	0.0276 (6)	0.0057 (5)	0.0114 (5)	−0.0020 (5)

Geometric parameters (Å, º) top

O1—N1	1.2888 (11)	C12—C13	1.3887 (15)
N1—C2	1.4988 (14)	C12—H12	0.971 (15)
N1—C6	1.4941 (13)	C13—C14	1.3899 (17)
N2—C4	1.4683 (13)	C13—H13	0.960 (14)
N2—C7	1.2659 (14)	C14—C15	1.3902 (17)
C2—C22	1.5323 (16)	C14—H14	0.979 (15)
C2—C3	1.5341 (14)	C15—C16	1.3914 (16)
C2—C21	1.5361 (15)	C15—H15	0.978 (14)
C3—C4	1.5247 (15)	C16—H16	0.961 (14)
C3—H31	1.015 (13)	C21—H21	1.012 (16)
C3—H32	0.980 (15)	C21—H22	0.970 (16)
C4—C5	1.5228 (15)	C21—H23	0.975 (16)
C4—H4	0.999 (12)	C22—H24	1.003 (15)
C5—C6	1.5314 (14)	C22—H25	0.992 (16)
C5—H51	1.004 (13)	C22—H26	0.990 (17)
C5—H52	1.013 (13)	C61—H61	0.991 (15)
C6—C62	1.5311 (15)	C61—H62	1.003 (16)
C6—C61	1.5380 (15)	C61—H63	0.991 (14)
C7—C11	1.4779 (14)	C62—H64	1.013 (15)
C7—H7	1.002 (13)	C62—H65	0.988 (15)
C11—C16	1.3966 (16)	C62—H66	1.018 (15)
C11—C12	1.3996 (15)

O1···O1ⁱ	5.5398 (9)	O1···H32ⁱⁱ	2.422 (15)
O1···O1ⁱⁱ	6.0841 (9)	O1···H22ⁱⁱ	2.657 (16)
O1···C3ⁱⁱ	3.3134 (14)	O1···H24ⁱ	2.755 (15)
O1···C21ⁱⁱ	3.3654 (16)	O1···H31ⁱ	3.028 (13)

O1—N1—C6	115.29 (8)	C13—C12—C11	120.04 (11)
O1—N1—C2	115.84 (8)	C13—C12—H12	120.5 (8)
C6—N1—C2	124.31 (8)	C11—C12—H12	119.5 (8)
C7—N2—C4	116.84 (9)	C12—C13—C14	120.56 (11)
N1—C2—C22	107.47 (9)	C12—C13—H13	119.2 (8)
N1—C2—C3	110.01 (8)	C14—C13—H13	120.2 (8)
C22—C2—C3	108.78 (9)	C13—C14—C15	119.71 (10)
N1—C2—C21	108.58 (9)	C13—C14—H14	122.5 (9)
C22—C2—C21	109.85 (10)	C15—C14—H14	117.8 (9)
C3—C2—C21	112.05 (9)	C14—C15—C16	120.01 (11)
C4—C3—C2	113.73 (9)	C14—C15—H15	120.0 (8)
C4—C3—H31	108.5 (7)	C16—C15—H15	120.0 (8)
C2—C3—H31	109.3 (7)	C15—C16—C11	120.53 (11)
C4—C3—H32	109.7 (8)	C15—C16—H16	120.2 (9)
C2—C3—H32	108.3 (8)	C11—C16—H16	119.2 (9)
H31—C3—H32	107.0 (11)	C2—C21—H21	111.9 (9)
N2—C4—C5	108.33 (9)	C2—C21—H22	110.0 (9)
N2—C4—C3	108.93 (8)	H21—C21—H22	108.9 (12)
C5—C4—C3	108.39 (9)	C2—C21—H23	108.6 (9)
N2—C4—H4	110.2 (7)	H21—C21—H23	107.3 (12)
C5—C4—H4	111.1 (7)	H22—C21—H23	110.1 (13)
C3—C4—H4	109.8 (7)	C2—C22—H24	111.7 (9)
C4—C5—C6	113.87 (9)	C2—C22—H25	109.1 (9)
C4—C5—H51	110.5 (8)	H24—C22—H25	108.5 (12)
C6—C5—H51	108.3 (8)	C2—C22—H26	110.5 (10)
C4—C5—H52	107.4 (8)	H24—C22—H26	106.2 (12)
C6—C5—H52	108.9 (8)	H25—C22—H26	110.8 (12)
H51—C5—H52	107.7 (10)	C6—C61—H61	112.0 (8)
N1—C6—C62	107.47 (9)	C6—C61—H62	109.2 (8)
N1—C6—C5	109.87 (8)	H61—C61—H62	107.9 (12)
C62—C6—C5	109.47 (9)	C6—C61—H63	110.8 (8)
N1—C6—C61	109.27 (9)	H61—C61—H63	107.8 (11)
C62—C6—C61	109.08 (9)	H62—C61—H63	109.0 (11)
C5—C6—C61	111.57 (9)	C6—C62—H64	108.4 (8)
N2—C7—C11	122.87 (10)	C6—C62—H65	111.6 (8)
N2—C7—H7	122.8 (7)	H64—C62—H65	109.3 (12)
C11—C7—H7	114.4 (7)	C6—C62—H66	111.4 (8)
C16—C11—C12	119.14 (10)	H64—C62—H66	109.5 (11)
C16—C11—C7	119.52 (10)	H65—C62—H66	106.7 (11)
C12—C11—C7	121.32 (10)

O1—N1—C2—C3	−170.02 (9)	O1—N1—C6—C62	50.63 (11)
O1—N1—C6—C5	169.67 (8)	C2—N1—C6—C62	−154.40 (9)
C6—N1—C2—C3	35.14 (13)	O1—N1—C6—C61	−67.61 (12)
C2—N1—C6—C5	−35.36 (13)	C2—N1—C6—C61	87.36 (11)
N1—C2—C3—C4	−45.73 (12)	C4—C5—C6—C62	164.18 (9)
C4—C5—C6—N1	46.37 (12)	C4—C5—C6—C61	−74.98 (12)
C2—C3—C4—C5	59.46 (11)	C4—N2—C7—C11	178.84 (9)
C3—C4—C5—C6	−59.89 (11)	N2—C7—C11—C16	−177.42 (11)
C2—C3—C4—N2	177.14 (8)	N2—C7—C11—C12	1.21 (17)
N2—C4—C5—C6	−177.95 (9)	C16—C11—C12—C13	0.82 (16)
C7—N2—C4—C3	112.82 (11)	C7—C11—C12—C13	−177.81 (10)
C7—N2—C4—C5	−129.47 (10)	C11—C12—C13—C14	−0.10 (17)
O1—N1—C2—C22	−51.74 (12)	C12—C13—C14—C15	−0.50 (17)
C6—N1—C2—C22	153.42 (9)	C13—C14—C15—C16	0.36 (17)
O1—N1—C2—C21	67.03 (12)	C14—C15—C16—C11	0.37 (17)
C6—N1—C2—C21	−87.80 (11)	C12—C11—C16—C15	−0.96 (17)
C22—C2—C3—C4	−163.20 (9)	C7—C11—C16—C15	177.70 (10)
C21—C2—C3—C4	75.15 (12)

Symmetry codes: (i) x, −y+3/2, z+1/2; (ii) −x+1, y+1/2, −z+1/2.

(9) 4-(4-methylthiophenylmethyleneamino)-2,2,6,6-tetramethylpiperidin-1-oxyl top

Crystal data top

C₁₇H₂₅N₂OS	D_x = 1.140 Mg m⁻³
M_r = 305.46	Melting point: not measured K
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
a = 13.5737 (18) Å	Cell parameters from 25 reflections
b = 11.8796 (18) Å	θ = 12.7–17.4°
c = 11.1628 (16) Å	µ = 0.18 mm⁻¹
β = 98.760 (11)°	T = 296 K
V = 1779.0 (4) Å³	Prism, orange
Z = 4	0.50 × 0.35 × 0.25 mm
F(000) = 660.00

Data collection top

Rigaku AFC7R diffractometer	R_int = 0.021
Radiation source: Rigaku rotating anode	θ_max = 27.5°, θ_min = 2.3°
Graphite monochromator	h = −17→17
ω–2θ scans	k = −15→0
4304 measured reflections	l = 0→14
4091 independent reflections	3 standard reflections every 150 reflections
2979 reflections with I > 2σ(I)	intensity decay: 0.0%

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: difmap and geom
R[F² > 2σ(F²)] = 0.040	All H-atom parameters refined
wR(F²) = 0.122	Calculated w = 1/[σ²(F_o²) + (0.0512P)² + 0.3325P] where P = (F_o² + 2F_c²)/3
S = 1.02	(Δ/σ)_max = 0.001
4091 reflections	Δρ_max = 0.23 e Å⁻³
291 parameters	Δρ_min = −0.26 e Å⁻³
0 restraints	Extinction correction: SHELXL-97 (Sheldrick, 1997), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0182 (16)

Special details top

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
S1	−0.00162 (4)	0.02068 (5)	−0.25419 (5)	0.0844 (2)
O1	0.46260 (11)	0.79174 (11)	0.31102 (13)	0.0891 (4)
N1	0.41586 (11)	0.71109 (11)	0.25022 (12)	0.0600 (3)
N2	0.26132 (10)	0.43938 (11)	0.06283 (11)	0.0605 (3)
C2	0.47918 (12)	0.61991 (15)	0.21142 (15)	0.0643 (4)
C3	0.41595 (12)	0.54164 (15)	0.12193 (15)	0.0593 (4)
C4	0.31724 (13)	0.50953 (13)	0.15815 (14)	0.0578 (4)
C5	0.25828 (13)	0.61645 (15)	0.16932 (17)	0.0622 (4)
C6	0.30903 (14)	0.69928 (14)	0.26370 (15)	0.0643 (4)
C7	0.25185 (11)	0.33698 (13)	0.08471 (15)	0.0563 (4)
C11	0.19525 (11)	0.25896 (12)	−0.00233 (14)	0.0533 (3)
C12	0.15500 (13)	0.29465 (14)	−0.11764 (15)	0.0598 (4)
C13	0.09536 (13)	0.22453 (15)	−0.19658 (17)	0.0651 (4)
C14	0.07558 (11)	0.11579 (13)	−0.16192 (16)	0.0605 (4)
C15	0.11745 (14)	0.07852 (14)	−0.04787 (18)	0.0697 (5)
C16	0.17698 (13)	0.14949 (14)	0.03093 (17)	0.0668 (4)
C17	−0.03879 (18)	0.0965 (2)	−0.3911 (2)	0.0909 (7)
C21	0.5274 (2)	0.5564 (2)	0.3249 (2)	0.0974 (8)
C22	0.55840 (18)	0.6752 (3)	0.1474 (3)	0.1001 (9)
C61	0.3010 (2)	0.6612 (2)	0.3924 (2)	0.0924 (7)
C62	0.2608 (2)	0.8159 (2)	0.2399 (3)	0.0926 (7)
H4	0.3256 (14)	0.4711 (15)	0.2354 (18)	0.074 (5)*
H7	0.2781 (13)	0.3074 (16)	0.1651 (17)	0.072 (5)*
H12	0.1686 (12)	0.3729 (15)	−0.1421 (15)	0.068 (5)*
H13	0.0711 (15)	0.2501 (16)	−0.2775 (18)	0.083 (6)*
H15	0.1035 (15)	0.0073 (18)	−0.0185 (19)	0.088 (6)*
H16	0.2066 (14)	0.1231 (16)	0.1116 (18)	0.085 (6)*
H21	0.475 (2)	0.517 (2)	0.370 (2)	0.112 (9)*
H22	0.570 (2)	0.507 (2)	0.304 (2)	0.115 (9)*
H23	0.5624 (17)	0.608 (2)	0.379 (2)	0.109 (8)*
H24	0.527 (2)	0.717 (2)	0.075 (3)	0.130 (11)*
H25	0.604 (2)	0.611 (3)	0.127 (3)	0.151 (11)*
H26	0.597 (2)	0.719 (2)	0.205 (2)	0.114 (8)*
H31	0.4018 (11)	0.5779 (13)	0.0419 (15)	0.056 (4)*
H32	0.4553 (14)	0.4802 (17)	0.1126 (17)	0.076 (5)*
H51	0.1941 (15)	0.5976 (16)	0.1939 (16)	0.082 (6)*
H52	0.2472 (13)	0.6548 (16)	0.0851 (18)	0.079 (5)*
H61	0.3311 (15)	0.5878 (19)	0.4123 (18)	0.081 (6)*
H62	0.2268 (18)	0.660 (2)	0.404 (2)	0.107 (8)*
H63	0.343 (2)	0.712 (2)	0.454 (2)	0.123 (9)*
H64	0.191 (2)	0.804 (2)	0.242 (2)	0.119 (9)*
H65	0.2836 (18)	0.866 (2)	0.307 (2)	0.113 (8)*
H66	0.278 (2)	0.849 (2)	0.154 (3)	0.142 (10)*
H71	0.020 (2)	0.117 (2)	−0.430 (2)	0.128 (9)*
H72	−0.0752 (19)	0.173 (2)	−0.372 (2)	0.125 (9)*
H73	−0.0835 (17)	0.0485 (19)	−0.436 (2)	0.100 (7)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0703 (3)	0.0738 (3)	0.1028 (4)	−0.0136 (2)	−0.0067 (3)	−0.0318 (3)
O1	0.1036 (10)	0.0652 (8)	0.0958 (10)	−0.0257 (7)	0.0070 (8)	−0.0334 (7)
N1	0.0720 (8)	0.0488 (7)	0.0583 (7)	−0.0103 (6)	0.0068 (6)	−0.0134 (6)
N2	0.0741 (8)	0.0498 (7)	0.0524 (7)	−0.0087 (6)	−0.0074 (6)	−0.0048 (5)
C2	0.0590 (9)	0.0672 (10)	0.0628 (9)	−0.0008 (7)	−0.0033 (7)	−0.0191 (8)
C3	0.0595 (9)	0.0570 (9)	0.0576 (9)	0.0045 (7)	−0.0031 (7)	−0.0168 (7)
C4	0.0740 (10)	0.0483 (8)	0.0467 (8)	−0.0091 (7)	−0.0051 (7)	−0.0038 (6)
C5	0.0599 (9)	0.0629 (10)	0.0649 (10)	−0.0069 (7)	0.0131 (8)	−0.0091 (8)
C6	0.0767 (11)	0.0577 (9)	0.0615 (9)	−0.0056 (8)	0.0206 (8)	−0.0128 (7)
C7	0.0582 (8)	0.0508 (8)	0.0555 (8)	−0.0018 (6)	−0.0053 (7)	−0.0019 (7)
C11	0.0517 (7)	0.0457 (7)	0.0594 (8)	0.0013 (6)	−0.0018 (6)	−0.0055 (6)
C12	0.0670 (9)	0.0495 (8)	0.0591 (9)	−0.0036 (7)	−0.0025 (7)	−0.0046 (7)
C13	0.0691 (10)	0.0618 (9)	0.0598 (9)	−0.0031 (8)	−0.0042 (8)	−0.0097 (8)
C14	0.0489 (8)	0.0565 (8)	0.0741 (10)	−0.0004 (6)	0.0026 (7)	−0.0198 (8)
C15	0.0712 (10)	0.0442 (8)	0.0897 (12)	−0.0048 (7)	−0.0009 (9)	−0.0042 (8)
C16	0.0713 (10)	0.0506 (8)	0.0729 (11)	−0.0011 (7)	−0.0077 (8)	0.0001 (8)
C17	0.0736 (13)	0.122 (2)	0.0748 (13)	−0.0213 (13)	0.0029 (10)	−0.0357 (13)
C21	0.1011 (18)	0.0918 (17)	0.0840 (15)	0.0198 (15)	−0.0354 (14)	−0.0221 (13)
C22	0.0672 (13)	0.135 (2)	0.0988 (18)	−0.0323 (14)	0.0159 (12)	−0.0432 (18)
C61	0.127 (2)	0.0910 (17)	0.0651 (12)	−0.0225 (15)	0.0346 (13)	−0.0150 (11)
C62	0.1033 (18)	0.0700 (13)	0.1089 (19)	0.0127 (12)	0.0305 (15)	−0.0216 (13)

Geometric parameters (Å, º) top

S1—C14	1.7626 (15)	C12—C13	1.381 (2)
S1—C17	1.780 (3)	C12—H12	0.994 (17)
O1—N1	1.2845 (16)	C13—C14	1.386 (2)
N1—C2	1.488 (2)	C13—H13	0.96 (2)
N1—C6	1.487 (2)	C14—C15	1.385 (2)
N2—C4	1.4687 (18)	C15—C16	1.386 (2)
N2—C7	1.251 (2)	C15—H15	0.94 (2)
C2—C22	1.527 (3)	C16—H16	0.98 (2)
C2—C3	1.529 (2)	C17—H71	1.00 (3)
C2—C21	1.533 (3)	C17—H72	1.07 (3)
C3—C4	1.506 (2)	C17—H73	0.92 (2)
C3—H31	0.984 (16)	C21—H21	1.04 (3)
C3—H32	0.92 (2)	C21—H22	0.88 (3)
C4—C5	1.517 (2)	C21—H23	0.94 (3)
C4—H4	0.968 (19)	C22—H24	0.99 (3)
C5—C6	1.527 (2)	C22—H25	1.03 (3)
C5—H51	0.978 (19)	C22—H26	0.92 (3)
C5—H52	1.035 (19)	C61—H61	0.98 (2)
C6—C61	1.525 (3)	C61—H62	1.03 (2)
C6—C62	1.538 (3)	C61—H63	1.02 (3)
C7—C11	1.472 (2)	C62—H64	0.97 (3)
C7—H7	0.979 (18)	C62—H65	0.97 (2)
C11—C16	1.385 (2)	C62—H66	1.10 (3)
C11—C12	1.386 (2)

O1···O1ⁱ	5.6688 (9)	O1···H32ⁱⁱ	2.59 (2)
O1···O1ⁱⁱ	6.2120 (12)	O1···H22ⁱⁱ	2.87 (3)
O1···C3ⁱⁱ	3.423 (2)	O1···H24ⁱ	2.95 (3)
O1···C21ⁱⁱ	3.503 (3)	O1···H31ⁱ	3.220 (16)

C14—S1—C17	104.07 (10)	C11—C12—H12	118.6 (10)
O1—N1—C6	115.32 (13)	C12—C13—C14	120.22 (16)
O1—N1—C2	115.86 (13)	C12—C13—H13	119.5 (12)
C6—N1—C2	125.19 (12)	C14—C13—H13	120.2 (12)
C7—N2—C4	117.87 (13)	C15—C14—C13	118.98 (14)
N1—C2—C22	107.58 (18)	C15—C14—S1	117.15 (13)
N1—C2—C3	109.96 (13)	C13—C14—S1	123.87 (14)
C22—C2—C3	108.73 (15)	C14—C15—C16	120.45 (16)
N1—C2—C21	108.09 (17)	C14—C15—H15	122.2 (13)
C22—C2—C21	110.8 (2)	C16—C15—H15	117.2 (13)
C3—C2—C21	111.55 (17)	C11—C16—C15	120.79 (16)
C4—C3—C2	114.35 (13)	C11—C16—H16	118.8 (11)
C4—C3—H31	107.2 (9)	C15—C16—H16	120.4 (11)
C2—C3—H31	109.9 (9)	S1—C17—H71	111.3 (15)
C4—C3—H32	112.6 (12)	S1—C17—H72	109.5 (14)
C2—C3—H32	106.2 (12)	H71—C17—H72	107 (2)
H31—C3—H32	106.3 (15)	S1—C17—H73	103.4 (14)
N2—C4—C3	109.38 (13)	H71—C17—H73	115 (2)
N2—C4—C5	108.29 (13)	H72—C17—H73	110.4 (19)
C3—C4—C5	108.19 (13)	C2—C21—H21	112.6 (14)
N2—C4—H4	110.8 (11)	C2—C21—H22	109.0 (18)
C3—C4—H4	111.7 (11)	H21—C21—H22	110 (2)
C5—C4—H4	108.3 (11)	C2—C21—H23	108.9 (15)
C4—C5—C6	114.09 (14)	H21—C21—H23	107 (2)
C4—C5—H51	109.6 (11)	H22—C21—H23	109 (2)
C6—C5—H51	106.4 (11)	C2—C22—H24	110.5 (17)
C4—C5—H52	107.4 (11)	C2—C22—H25	105.9 (17)
C6—C5—H52	109.3 (11)	H24—C22—H25	113 (2)
H51—C5—H52	110.1 (15)	C2—C22—H26	106.7 (16)
N1—C6—C61	109.50 (18)	H24—C22—H26	114 (2)
N1—C6—C5	109.60 (13)	H25—C22—H26	106 (2)
C61—C6—C5	111.67 (16)	C6—C61—H61	113.1 (12)
N1—C6—C62	107.06 (16)	C6—C61—H62	109.1 (13)
C61—C6—C62	109.88 (18)	H61—C61—H62	110.3 (18)
C5—C6—C62	109.01 (17)	C6—C61—H63	110.1 (14)
N2—C7—C11	122.83 (14)	H61—C61—H63	102.2 (18)
N2—C7—H7	119.6 (11)	H62—C61—H63	111.9 (19)
C11—C7—H7	117.4 (11)	C6—C62—H64	104.9 (16)
C16—C11—C12	118.35 (14)	C6—C62—H65	109.9 (15)
C16—C11—C7	120.73 (14)	H64—C62—H65	106 (2)
C12—C11—C7	120.85 (14)	C6—C62—H66	109.6 (15)
C13—C12—C11	121.19 (15)	H64—C62—H66	114 (2)
C13—C12—H12	120.2 (10)	H65—C62—H66	112 (2)

O1—N1—C2—C3	−169.95 (15)	O1—N1—C6—C62	51.1 (2)
O1—N1—C6—C5	169.16 (14)	C2—N1—C6—C62	−151.41 (17)
C6—N1—C2—C3	32.6 (2)	C4—C5—C6—C61	−75.9 (2)
C2—N1—C6—C5	−33.3 (2)	C4—C5—C6—C62	162.54 (17)
N1—C2—C3—C4	−44.4 (2)	C4—N2—C7—C11	178.33 (14)
C4—C5—C6—N1	45.7 (2)	N2—C7—C11—C16	−172.43 (17)
C2—C3—C4—C5	59.37 (18)	N2—C7—C11—C12	4.5 (3)
C3—C4—C5—C6	−60.16 (18)	C16—C11—C12—C13	2.1 (3)
C2—C3—C4—N2	177.13 (14)	C7—C11—C12—C13	−174.95 (16)
N2—C4—C5—C6	−178.61 (14)	C11—C12—C13—C14	−0.8 (3)
C7—N2—C4—C3	108.56 (17)	C12—C13—C14—C15	−0.8 (3)
C7—N2—C4—C5	−133.75 (16)	C12—C13—C14—S1	178.53 (13)
O1—N1—C2—C22	−51.7 (2)	C17—S1—C14—C15	−179.08 (15)
C6—N1—C2—C22	150.90 (18)	C17—S1—C14—C13	1.60 (18)
O1—N1—C2—C21	68.1 (2)	C13—C14—C15—C16	0.9 (3)
C6—N1—C2—C21	−89.3 (2)	S1—C14—C15—C16	−178.40 (14)
C22—C2—C3—C4	−161.99 (19)	C12—C11—C16—C15	−1.9 (3)
C21—C2—C3—C4	75.5 (2)	C7—C11—C16—C15	175.14 (16)
O1—N1—C6—C61	−68.0 (2)	C14—C15—C16—C11	0.4 (3)
C2—N1—C6—C61	89.50 (19)

Symmetry codes: (i) x, −y+3/2, z+1/2; (ii) −x+1, y+1/2, −z+1/2.

(10) 4-(3-pyridylmethyleneamino)-2,2,6,6-tetramethylpiperidin-1-oxyl top

Crystal data top

C₁₅H₂₂N₃O	F(000) = 564.00
M_r = 260.36	D_x = 1.153 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
a = 12.425 (5) Å	Cell parameters from 25 reflections
b = 11.598 (4) Å	θ = 12.7–17.4°
c = 11.038 (5) Å	µ = 0.07 mm⁻¹
β = 109.53 (4)°	T = 297 K
V = 1499.3 (10) Å³	Prism, orange
Z = 4	0.20 × 0.20 × 0.20 mm

Data collection top

Rigaku AFC5R diffractometer	R_int = 0.020
Radiation source: Rigaku rotating anode	θ_max = 27.5°, θ_min = 2.5°
Graphite monochromator	h = −16→15
ω–2θ scans	k = 0→15
3608 measured reflections	l = 0→14
3432 independent reflections	3 standard reflections every 100 reflections
2096 reflections with I > 2σ(I)	intensity decay: 0.1%

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: difmap and geom
R[F² > 2σ(F²)] = 0.049	All H-atom parameters refined
wR(F²) = 0.135	Calculated w = 1/[σ²(F_o²) + (0.058P)² + 0.2599P] where P = (F_o² + 2F_c²)/3
S = 0.98	(Δ/σ)_max = 0.002
3432 reflections	Δρ_max = 0.15 e Å⁻³
261 parameters	Δρ_min = −0.12 e Å⁻³
0 restraints	Extinction correction: SHELXL-97 (Sheldrick, 1997), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.038 (3)

Special details top

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
O1	0.46505 (12)	0.78860 (11)	0.32658 (13)	0.0650 (4)
N1	0.40835 (12)	0.71122 (12)	0.24780 (13)	0.0443 (4)
N2	0.22071 (13)	0.45312 (13)	−0.00520 (13)	0.0496 (4)
N3	0.08599 (17)	0.08994 (16)	−0.2040 (2)	0.0828 (6)
C2	0.47748 (14)	0.61872 (15)	0.21527 (16)	0.0466 (4)
C3	0.40218 (15)	0.54721 (16)	0.10254 (17)	0.0454 (4)
C4	0.28812 (15)	0.51259 (15)	0.11344 (16)	0.0441 (4)
C5	0.22439 (16)	0.62034 (16)	0.12696 (18)	0.0466 (4)
C6	0.28714 (15)	0.69687 (15)	0.24096 (16)	0.0450 (4)
C7	0.21370 (15)	0.34642 (17)	−0.00312 (18)	0.0499 (5)
C11	0.14925 (15)	0.27791 (15)	−0.11654 (17)	0.0499 (5)
C12	0.09159 (17)	0.3275 (2)	−0.23400 (19)	0.0568 (5)
C13	0.03221 (18)	0.2568 (2)	−0.3345 (2)	0.0665 (6)
C14	0.03225 (19)	0.1405 (2)	−0.3149 (2)	0.0721 (7)
C16	0.14359 (19)	0.15965 (19)	−0.1079 (2)	0.0702 (6)
C21	0.5317 (2)	0.5441 (2)	0.3348 (2)	0.0668 (6)
C22	0.5702 (2)	0.6771 (3)	0.1752 (3)	0.0713 (7)
C61	0.2840 (2)	0.6460 (2)	0.3678 (2)	0.0606 (6)
C62	0.2319 (2)	0.8162 (2)	0.2199 (3)	0.0631 (6)
H4	0.2982 (13)	0.4591 (14)	0.1863 (16)	0.039 (4)*
H7	0.2502 (17)	0.3041 (18)	0.074 (2)	0.067 (6)*
H12	0.0932 (16)	0.4083 (19)	−0.2439 (18)	0.063 (6)*
H13	−0.007 (2)	0.2870 (19)	−0.414 (2)	0.080 (7)*
H14	−0.0077 (18)	0.090 (2)	−0.381 (2)	0.080 (7)*
H16	0.183 (2)	0.125 (2)	−0.026 (2)	0.083 (7)*
H21	0.472 (2)	0.499 (2)	0.358 (2)	0.095 (9)*
H22	0.583 (2)	0.493 (2)	0.320 (2)	0.080 (7)*
H23	0.5723 (17)	0.5916 (18)	0.406 (2)	0.067 (6)*
H24	0.5387 (19)	0.721 (2)	0.098 (2)	0.077 (7)*
H25	0.619 (2)	0.618 (2)	0.153 (2)	0.104 (9)*
H26	0.623 (2)	0.724 (2)	0.247 (2)	0.083 (7)*
H31	0.3875 (14)	0.5912 (15)	0.0224 (17)	0.047 (5)*
H32	0.4456 (15)	0.4786 (17)	0.0933 (17)	0.054 (5)*
H51	0.1500 (16)	0.6015 (16)	0.1351 (17)	0.060 (5)*
H52	0.2098 (15)	0.6630 (16)	0.0478 (18)	0.054 (5)*
H61	0.3117 (17)	0.565 (2)	0.3784 (19)	0.067 (6)*
H62	0.205 (2)	0.643 (2)	0.368 (2)	0.091 (8)*
H63	0.3339 (18)	0.6895 (18)	0.440 (2)	0.070 (6)*
H64	0.148 (2)	0.8059 (19)	0.204 (2)	0.077 (7)*
H65	0.2633 (19)	0.865 (2)	0.290 (2)	0.080 (7)*
H66	0.2381 (18)	0.853 (2)	0.143 (2)	0.076 (7)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0709 (9)	0.0530 (8)	0.0679 (9)	−0.0191 (7)	0.0190 (7)	−0.0245 (7)
N1	0.0517 (8)	0.0387 (8)	0.0410 (7)	−0.0067 (7)	0.0135 (6)	−0.0071 (6)
N2	0.0581 (9)	0.0438 (9)	0.0401 (8)	−0.0085 (7)	0.0072 (7)	−0.0060 (6)
N3	0.0742 (12)	0.0538 (11)	0.0978 (15)	0.0002 (9)	−0.0014 (11)	−0.0300 (11)
C2	0.0447 (10)	0.0512 (11)	0.0401 (9)	0.0020 (8)	0.0093 (7)	−0.0075 (8)
C3	0.0512 (10)	0.0443 (10)	0.0373 (9)	0.0047 (8)	0.0101 (8)	−0.0062 (8)
C4	0.0554 (11)	0.0374 (9)	0.0347 (8)	−0.0051 (8)	0.0085 (7)	−0.0021 (7)
C5	0.0453 (10)	0.0494 (11)	0.0435 (10)	−0.0042 (8)	0.0129 (8)	−0.0027 (8)
C6	0.0492 (10)	0.0431 (10)	0.0447 (9)	−0.0026 (8)	0.0183 (8)	−0.0060 (8)
C7	0.0516 (11)	0.0448 (11)	0.0467 (10)	−0.0006 (8)	0.0077 (9)	−0.0034 (8)
C11	0.0447 (10)	0.0466 (10)	0.0545 (10)	0.0000 (8)	0.0115 (8)	−0.0117 (8)
C12	0.0564 (11)	0.0586 (13)	0.0522 (11)	−0.0028 (10)	0.0139 (9)	−0.0088 (10)
C13	0.0532 (12)	0.0864 (17)	0.0526 (12)	−0.0040 (11)	0.0080 (10)	−0.0150 (12)
C14	0.0542 (12)	0.0752 (16)	0.0760 (15)	−0.0022 (12)	0.0071 (11)	−0.0393 (14)
C16	0.0663 (14)	0.0506 (12)	0.0755 (15)	0.0037 (10)	−0.0005 (12)	−0.0129 (11)
C21	0.0670 (15)	0.0715 (15)	0.0470 (11)	0.0175 (13)	−0.0006 (11)	−0.0066 (11)
C22	0.0505 (12)	0.102 (2)	0.0640 (15)	−0.0184 (13)	0.0224 (11)	−0.0215 (14)
C61	0.0734 (15)	0.0653 (15)	0.0491 (11)	−0.0127 (12)	0.0284 (11)	−0.0075 (10)
C62	0.0702 (15)	0.0506 (12)	0.0709 (15)	0.0084 (11)	0.0270 (12)	−0.0089 (11)

Geometric parameters (Å, º) top

O1—N1	1.2839 (17)	C7—H7	0.96 (2)
N1—C2	1.491 (2)	C11—C16	1.378 (3)
N1—C6	1.492 (2)	C11—C12	1.380 (3)
N2—C4	1.469 (2)	C12—C13	1.378 (3)
N2—C7	1.241 (2)	C12—H12	0.94 (2)
N3—C14	1.319 (3)	C13—C14	1.365 (4)
N3—C16	1.335 (3)	C13—H13	0.92 (2)
C2—C22	1.523 (3)	C14—H14	0.94 (2)
C2—C3	1.528 (2)	C16—H16	0.96 (2)
C2—C21	1.533 (3)	C21—H21	1.01 (3)
C3—C4	1.516 (3)	C21—H22	0.93 (2)
C3—H31	0.984 (18)	C21—H23	0.95 (2)
C3—H32	0.986 (19)	C22—H24	0.96 (2)
C4—C5	1.513 (3)	C22—H25	1.00 (3)
C4—H4	0.990 (17)	C22—H26	1.00 (2)
C5—C6	1.524 (2)	C61—H61	1.00 (2)
C5—H51	0.983 (19)	C61—H62	0.98 (3)
C5—H52	0.967 (19)	C61—H63	0.97 (2)
C6—C62	1.528 (3)	C62—H64	1.00 (2)
C6—C61	1.532 (3)	C62—H65	0.94 (2)
C7—C11	1.473 (2)	C62—H66	0.98 (2)

O1···O1ⁱ	5.591 (2)	O1···H32ⁱⁱ	2.49 (2)
O1···O1ⁱⁱ	6.183 (2)	O1···H22ⁱⁱ	2.82 (2)
O1···O1ⁱⁱⁱ	6.102 (3)	O1···H24ⁱ	2.82 (2)
O1···C3ⁱⁱ	3.386 (2)	O1···H31ⁱ	2.99 (2)
O1···C21ⁱⁱ	3.464 (3)

O1—N1—C2	115.86 (14)	C16—C11—C7	120.27 (19)
O1—N1—C6	115.36 (13)	C12—C11—C7	122.54 (18)
C2—N1—C6	124.10 (13)	C13—C12—C11	118.6 (2)
C7—N2—C4	118.30 (16)	C13—C12—H12	121.6 (12)
C14—N3—C16	116.0 (2)	C11—C12—H12	119.8 (12)
N1—C2—C22	107.60 (17)	C14—C13—C12	119.2 (2)
N1—C2—C3	109.97 (14)	C14—C13—H13	120.1 (15)
C22—C2—C3	108.74 (16)	C12—C13—H13	120.7 (15)
N1—C2—C21	108.79 (16)	N3—C14—C13	124.0 (2)
C22—C2—C21	110.08 (19)	N3—C14—H14	114.9 (14)
C3—C2—C21	111.58 (17)	C13—C14—H14	121.1 (14)
C4—C3—C2	114.42 (15)	N3—C16—C11	125.0 (2)
C4—C3—H31	108.2 (10)	N3—C16—H16	117.5 (14)
C2—C3—H31	109.2 (10)	C11—C16—H16	117.5 (14)
C4—C3—H32	110.7 (10)	C2—C21—H21	111.1 (14)
C2—C3—H32	108.4 (10)	C2—C21—H22	109.7 (14)
H31—C3—H32	105.6 (15)	H21—C21—H22	109 (2)
N2—C4—C5	108.32 (14)	C2—C21—H23	109.9 (13)
N2—C4—C3	108.85 (14)	H21—C21—H23	109 (2)
C5—C4—C3	108.84 (15)	H22—C21—H23	108.1 (18)
N2—C4—H4	108.0 (9)	C2—C22—H24	111.9 (14)
C5—C4—H4	111.5 (9)	C2—C22—H25	110.1 (15)
C3—C4—H4	111.3 (9)	H24—C22—H25	105 (2)
C4—C5—C6	114.97 (15)	C2—C22—H26	112.0 (14)
C4—C5—H51	111.4 (11)	H24—C22—H26	112.3 (19)
C6—C5—H51	106.9 (11)	H25—C22—H26	105.4 (19)
C4—C5—H52	106.2 (11)	C6—C61—H61	111.0 (12)
C6—C5—H52	109.8 (11)	C6—C61—H62	110.3 (14)
H51—C5—H52	107.4 (15)	H61—C61—H62	105.7 (19)
N1—C6—C5	109.63 (14)	C6—C61—H63	110.3 (12)
N1—C6—C62	107.54 (16)	H61—C61—H63	107.1 (17)
C5—C6—C62	108.78 (17)	H62—C61—H63	112.3 (19)
N1—C6—C61	109.30 (16)	C6—C62—H64	107.8 (13)
C5—C6—C61	111.59 (16)	C6—C62—H65	112.5 (14)
C62—C6—C61	109.91 (18)	H64—C62—H65	109.9 (19)
N2—C7—C11	122.93 (18)	C6—C62—H66	111.5 (13)
N2—C7—H7	120.9 (12)	H64—C62—H66	106.1 (18)
C11—C7—H7	116.2 (12)	H65—C62—H66	108.9 (19)
C16—C11—C12	117.18 (19)

O1—N1—C2—C3	−169.04 (14)	O1—N1—C6—C62	51.0 (2)
O1—N1—C6—C5	169.11 (14)	C2—N1—C6—C62	−154.35 (16)
C6—N1—C2—C3	36.4 (2)	O1—N1—C6—C61	−68.29 (19)
C2—N1—C6—C5	−36.2 (2)	C2—N1—C6—C61	86.37 (19)
N1—C2—C3—C4	−45.6 (2)	C4—C5—C6—C62	162.94 (17)
C4—C5—C6—N1	45.6 (2)	C4—C5—C6—C61	−75.6 (2)
C2—C3—C4—C5	57.4 (2)	C4—N2—C7—C11	−179.51 (16)
C3—C4—C5—C6	−57.7 (2)	N2—C7—C11—C16	−179.3 (2)
C2—C3—C4—N2	175.29 (14)	N2—C7—C11—C12	0.0 (3)
N2—C4—C5—C6	−175.87 (15)	C16—C11—C12—C13	0.2 (3)
C7—N2—C4—C3	102.9 (2)	C7—C11—C12—C13	−179.13 (18)
C7—N2—C4—C5	−138.93 (18)	C11—C12—C13—C14	0.0 (3)
O1—N1—C2—C22	−50.75 (19)	C16—N3—C14—C13	−0.6 (4)
C6—N1—C2—C22	154.70 (16)	C12—C13—C14—N3	0.2 (4)
O1—N1—C2—C21	68.5 (2)	C14—N3—C16—C11	0.8 (4)
C6—N1—C2—C21	−86.1 (2)	C12—C11—C16—N3	−0.6 (3)
C22—C2—C3—C4	−163.18 (19)	C7—C11—C16—N3	178.7 (2)
C21—C2—C3—C4	75.2 (2)

Symmetry codes: (i) x, −y+3/2, z+1/2; (ii) −x+1, y+1/2, −z+1/2; (iii) −x+1, −y+2, −z+1.

(11a) 4-(4-methylphenylmethyleneamino)-2,2,6,6-tetramethylpiperidin-1-oxyl top

Crystal data top

C₁₇H₂₅N₂O	F(000) = 596.00
M_r = 273.40	D_x = 1.120 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
a = 12.490 (3) Å	Cell parameters from 25 reflections
b = 11.597 (5) Å	θ = 17.3–17.5°
c = 11.280 (6) Å	µ = 0.07 mm⁻¹
β = 97.12 (3)°	T = 294 K
V = 1621.3 (11) Å³	Plate, orange
Z = 4	0.40 × 0.40 × 0.10 mm

Data collection top

Rigaku AFC7R diffractometer	R_int = 0.022
Radiation source: Rigaku rotating anode	θ_max = 27.5°, θ_min = 2.4°
Graphite monochromator	h = −16→16
ω–2θ scans	k = −15→0
3911 measured reflections	l = 0→14
3722 independent reflections	3 standard reflections every 150 reflections
2582 reflections with I > 2σ(I)	intensity decay: 2.4%

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: difmap and geom
R[F² > 2σ(F²)] = 0.050	All H-atom parameters refined
wR(F²) = 0.162	Calculated w = 1/[σ²(F_o²) + (0.0786P)² + 0.2899P] where P = (F_o² + 2F_c²)/3
S = 1.04	(Δ/σ)_max = 0.004
3722 reflections	Δρ_max = 0.20 e Å⁻³
282 parameters	Δρ_min = −0.15 e Å⁻³
0 restraints	Extinction correction: SHELXL-97 (Sheldrick, 1997), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.010 (2)

Special details top

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
O1	0.47665 (10)	0.78157 (11)	0.14265 (12)	0.0663 (4)
N1	0.42132 (10)	0.70948 (11)	0.19654 (12)	0.0476 (3)
N2	0.23830 (12)	0.47052 (12)	0.37066 (12)	0.0539 (4)
C2	0.48471 (12)	0.61885 (14)	0.26858 (14)	0.0509 (4)
C3	0.41239 (13)	0.55485 (15)	0.34689 (15)	0.0501 (4)
C4	0.30318 (13)	0.52061 (13)	0.28352 (15)	0.0492 (4)
C5	0.24614 (13)	0.62848 (15)	0.23262 (16)	0.0503 (4)
C6	0.30651 (13)	0.69569 (14)	0.14480 (14)	0.0494 (4)
C7	0.23144 (13)	0.36302 (14)	0.37570 (15)	0.0497 (4)
C11	0.16801 (12)	0.30377 (13)	0.45921 (14)	0.0487 (4)
C12	0.10994 (16)	0.36414 (17)	0.53603 (18)	0.0626 (5)
C13	0.04934 (17)	0.30621 (18)	0.61150 (19)	0.0669 (5)
C14	0.04532 (13)	0.18678 (16)	0.61391 (16)	0.0556 (4)
C15	0.10336 (15)	0.12749 (16)	0.5377 (2)	0.0649 (5)
C16	0.16365 (15)	0.18427 (15)	0.46089 (19)	0.0613 (5)
C17	−0.02015 (19)	0.1237 (3)	0.6978 (2)	0.0743 (6)
C21	0.5326 (2)	0.5364 (2)	0.1819 (2)	0.0735 (6)
C22	0.57458 (18)	0.6783 (3)	0.3488 (2)	0.0780 (7)
C61	0.3017 (2)	0.6350 (2)	0.02434 (17)	0.0680 (5)
C62	0.25774 (18)	0.81659 (18)	0.1280 (2)	0.0683 (5)
H4	0.3095 (14)	0.4647 (14)	0.2192 (15)	0.051 (4)*
H7	0.2627 (17)	0.3144 (19)	0.317 (2)	0.080 (6)*
H12	0.1111 (18)	0.445 (2)	0.534 (2)	0.082 (7)*
H13	0.010 (2)	0.349 (2)	0.664 (2)	0.091 (7)*
H15	0.1021 (18)	0.045 (2)	0.541 (2)	0.084 (7)*
H16	0.2028 (18)	0.1411 (19)	0.408 (2)	0.077 (6)*
H21	0.471 (2)	0.486 (3)	0.128 (3)	0.115 (9)*
H22	0.577 (2)	0.487 (2)	0.224 (3)	0.114 (10)*
H23	0.5712 (19)	0.578 (2)	0.128 (2)	0.090 (7)*
H24	0.544 (2)	0.735 (2)	0.403 (2)	0.094 (8)*
H25	0.617 (2)	0.622 (2)	0.398 (3)	0.103 (8)*
H26	0.622 (2)	0.720 (2)	0.301 (2)	0.102 (8)*
H31	0.3992 (13)	0.6047 (15)	0.4166 (16)	0.049 (4)*
H32	0.4529 (16)	0.4872 (18)	0.3789 (19)	0.069 (6)*
H51	0.1756 (16)	0.6090 (16)	0.1907 (17)	0.059 (5)*
H52	0.2365 (14)	0.6795 (15)	0.3034 (16)	0.054 (5)*
H61	0.3255 (17)	0.554 (2)	0.032 (2)	0.078 (6)*
H62	0.229 (2)	0.642 (2)	−0.018 (2)	0.097 (8)*
H63	0.3492 (18)	0.6748 (18)	−0.028 (2)	0.075 (6)*
H64	0.181 (2)	0.807 (2)	0.089 (2)	0.090 (7)*
H65	0.293 (2)	0.859 (2)	0.068 (2)	0.094 (7)*
H66	0.2626 (19)	0.860 (2)	0.207 (2)	0.089 (7)*
H71	−0.012 (3)	0.162 (4)	0.774 (4)	0.179 (17)*
H72	−0.087 (3)	0.119 (3)	0.671 (3)	0.139 (12)*
H73	0.019 (3)	0.060 (3)	0.737 (3)	0.143 (12)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0651 (8)	0.0581 (7)	0.0788 (8)	−0.0142 (6)	0.0211 (6)	0.0164 (6)
N1	0.0498 (7)	0.0426 (7)	0.0526 (7)	−0.0055 (5)	0.0150 (6)	0.0038 (5)
N2	0.0627 (8)	0.0455 (7)	0.0573 (8)	−0.0085 (6)	0.0226 (6)	−0.0003 (6)
C2	0.0455 (8)	0.0550 (9)	0.0540 (9)	0.0013 (7)	0.0128 (7)	0.0074 (7)
C3	0.0528 (9)	0.0478 (8)	0.0518 (9)	0.0031 (7)	0.0149 (7)	0.0075 (7)
C4	0.0576 (9)	0.0409 (8)	0.0524 (8)	−0.0057 (7)	0.0200 (7)	−0.0009 (6)
C5	0.0463 (8)	0.0515 (9)	0.0542 (9)	−0.0054 (7)	0.0105 (7)	0.0028 (7)
C6	0.0488 (8)	0.0494 (9)	0.0508 (8)	−0.0031 (7)	0.0098 (7)	0.0043 (7)
C7	0.0513 (9)	0.0454 (8)	0.0545 (9)	−0.0020 (6)	0.0154 (7)	0.0017 (7)
C11	0.0464 (8)	0.0456 (8)	0.0549 (9)	−0.0022 (6)	0.0098 (7)	0.0057 (6)
C12	0.0733 (12)	0.0484 (9)	0.0710 (11)	−0.0039 (8)	0.0282 (9)	−0.0017 (8)
C13	0.0720 (12)	0.0657 (12)	0.0686 (11)	−0.0040 (9)	0.0308 (9)	−0.0030 (9)
C14	0.0408 (8)	0.0664 (10)	0.0598 (9)	−0.0040 (7)	0.0069 (7)	0.0149 (8)
C15	0.0616 (11)	0.0475 (9)	0.0892 (13)	0.0018 (8)	0.0241 (10)	0.0178 (9)
C16	0.0628 (10)	0.0469 (9)	0.0794 (12)	0.0039 (8)	0.0290 (9)	0.0074 (8)
C17	0.0519 (11)	0.0990 (17)	0.0737 (13)	−0.0116 (11)	0.0144 (10)	0.0272 (12)
C21	0.0776 (14)	0.0710 (13)	0.0795 (13)	0.0230 (11)	0.0400 (12)	0.0139 (11)
C22	0.0542 (11)	0.1041 (18)	0.0744 (13)	−0.0186 (12)	0.0020 (10)	0.0171 (13)
C61	0.0762 (13)	0.0766 (14)	0.0513 (10)	−0.0143 (11)	0.0082 (9)	−0.0009 (9)
C62	0.0646 (12)	0.0615 (12)	0.0812 (14)	0.0095 (9)	0.0190 (10)	0.0223 (10)

Geometric parameters (Å, º) top

O1—N1	1.2846 (16)	C12—H12	0.94 (2)
N1—C2	1.494 (2)	C13—C14	1.386 (3)
N1—C6	1.488 (2)	C13—H13	0.95 (3)
N2—C4	1.4690 (19)	C14—C15	1.376 (3)
N2—C7	1.251 (2)	C14—C17	1.514 (2)
C2—C22	1.517 (3)	C15—C16	1.383 (3)
C2—C3	1.531 (2)	C15—H15	0.96 (2)
C2—C21	1.541 (3)	C16—H16	0.96 (2)
C3—C4	1.513 (2)	C17—H71	0.97 (5)
C3—H31	1.006 (18)	C17—H72	0.85 (3)
C3—H32	0.98 (2)	C17—H73	0.96 (4)
C4—C5	1.517 (2)	C21—H21	1.09 (3)
C4—H4	0.984 (17)	C21—H22	0.89 (3)
C5—C6	1.531 (2)	C21—H23	0.95 (3)
C5—H51	0.973 (19)	C22—H24	1.00 (3)
C5—H52	1.014 (18)	C22—H25	0.97 (3)
C6—C61	1.525 (3)	C22—H26	0.98 (3)
C6—C62	1.531 (3)	C61—H61	0.98 (2)
C7—C11	1.474 (2)	C61—H62	0.97 (3)
C7—H7	0.99 (2)	C61—H63	1.00 (2)
C11—C12	1.387 (2)	C62—H64	1.01 (3)
C11—C16	1.387 (2)	C62—H65	0.99 (3)
C12—C13	1.382 (3)	C62—H66	1.02 (3)

O1···O1ⁱ	5.688 (3)	O1···H32ⁱⁱ	2.56 (2)
O1···O1ⁱⁱ	6.283 (2)	O1···H22ⁱⁱ	2.94 (3)
O1···O1ⁱⁱⁱ	6.069 (3)	O1···H24^iv	2.94 (3)
O1···C3ⁱⁱ	3.455 (2)	O1···H31^iv	2.926 (18)
O1···C21ⁱⁱ	3.567 (3)

O1—N1—C6	115.66 (13)	C12—C13—C14	121.46 (18)
O1—N1—C2	115.80 (12)	C12—C13—H13	119.3 (15)
C6—N1—C2	123.89 (12)	C14—C13—H13	119.2 (15)
C7—N2—C4	118.09 (14)	C15—C14—C13	117.63 (16)
N1—C2—C22	107.91 (16)	C15—C14—C17	121.11 (19)
N1—C2—C3	110.12 (12)	C13—C14—C17	121.26 (19)
C22—C2—C3	108.79 (15)	C14—C15—C16	121.58 (18)
N1—C2—C21	108.23 (15)	C14—C15—H15	117.4 (14)
C22—C2—C21	110.08 (18)	C16—C15—H15	121.0 (14)
C3—C2—C21	111.63 (16)	C15—C16—C11	120.63 (17)
C4—C3—C2	114.62 (14)	C15—C16—H16	120.1 (13)
C4—C3—H31	107.2 (10)	C11—C16—H16	119.2 (13)
C2—C3—H31	109.7 (10)	C14—C17—H71	110 (3)
C4—C3—H32	111.0 (12)	C14—C17—H72	113 (2)
C2—C3—H32	106.7 (12)	H71—C17—H72	110 (3)
H31—C3—H32	107.4 (15)	C14—C17—H73	112.4 (19)
N2—C4—C3	109.13 (13)	H71—C17—H73	87 (3)
N2—C4—C5	107.89 (13)	H72—C17—H73	122 (3)
C3—C4—C5	108.43 (13)	C2—C21—H21	112.8 (15)
N2—C4—H4	109.5 (10)	C2—C21—H22	109.1 (18)
C3—C4—H4	111.8 (10)	H21—C21—H22	107 (2)
C5—C4—H4	110.0 (10)	C2—C21—H23	110.9 (15)
C4—C5—C6	114.77 (13)	H21—C21—H23	107 (2)
C4—C5—H51	110.3 (11)	H22—C21—H23	109 (2)
C6—C5—H51	107.0 (11)	C2—C22—H24	110.7 (15)
C4—C5—H52	106.2 (10)	C2—C22—H25	110.4 (16)
C6—C5—H52	109.2 (10)	H24—C22—H25	109 (2)
H51—C5—H52	109.3 (15)	C2—C22—H26	110.7 (16)
N1—C6—C61	109.17 (15)	H24—C22—H26	108 (2)
N1—C6—C5	109.21 (13)	H25—C22—H26	108 (2)
C61—C6—C5	111.96 (15)	C6—C61—H61	112.8 (13)
N1—C6—C62	107.42 (14)	C6—C61—H62	109.1 (15)
C61—C6—C62	109.95 (17)	H61—C61—H62	111.6 (19)
C5—C6—C62	109.03 (14)	C6—C61—H63	110.6 (12)
N2—C7—C11	122.60 (15)	H61—C61—H63	107.1 (17)
N2—C7—H7	120.1 (13)	H62—C61—H63	105.4 (19)
C11—C7—H7	117.0 (13)	C6—C62—H64	107.0 (13)
C12—C11—C16	118.13 (15)	C6—C62—H65	109.3 (14)
C12—C11—C7	121.89 (15)	H64—C62—H65	104.2 (19)
C16—C11—C7	119.97 (15)	C6—C62—H66	111.4 (13)
C13—C12—C11	120.57 (18)	H64—C62—H66	112.5 (19)
C13—C12—H12	120.9 (14)	H65—C62—H66	112.0 (19)
C11—C12—H12	118.5 (14)

O1—N1—C2—C3	168.74 (13)	C2—N1—C6—C61	−85.36 (18)
O1—N1—C6—C5	−167.92 (13)	O1—N1—C6—C62	−49.80 (19)
C6—N1—C2—C3	−36.5 (2)	C2—N1—C6—C62	155.45 (15)
C2—N1—C6—C5	37.34 (19)	C4—C5—C6—C61	73.8 (2)
N1—C2—C3—C4	45.18 (19)	C4—C5—C6—C62	−164.33 (16)
C4—C5—C6—N1	−47.24 (19)	C4—N2—C7—C11	−179.61 (14)
C2—C3—C4—C5	−57.23 (18)	N2—C7—C11—C12	1.3 (3)
C3—C4—C5—C6	58.65 (18)	N2—C7—C11—C16	−179.85 (18)
C2—C3—C4—N2	−174.51 (13)	C16—C11—C12—C13	−0.2 (3)
N2—C4—C5—C6	176.72 (13)	C7—C11—C12—C13	178.60 (17)
C7—N2—C4—C3	−100.27 (18)	C11—C12—C13—C14	0.6 (3)
C7—N2—C4—C5	142.12 (16)	C12—C13—C14—C15	−0.4 (3)
O1—N1—C2—C22	50.1 (2)	C12—C13—C14—C17	179.3 (2)
C6—N1—C2—C22	−155.16 (16)	C13—C14—C15—C16	−0.1 (3)
O1—N1—C2—C21	−68.98 (19)	C17—C14—C15—C16	−179.8 (2)
C6—N1—C2—C21	85.74 (19)	C14—C15—C16—C11	0.5 (3)
C22—C2—C3—C4	163.26 (18)	C12—C11—C16—C15	−0.3 (3)
C21—C2—C3—C4	−75.1 (2)	C7—C11—C16—C15	−179.18 (17)
O1—N1—C6—C61	69.38 (19)

Symmetry codes: (i) x, −y+3/2, z+1/2; (ii) −x+1, y+1/2, −z+1/2; (iii) −x+1, −y+2, −z; (iv) x, −y+3/2, z−1/2.

(11b) 4-(4-methylphenylmethyleneamino)-2,2,6,6-tetramethylpiperidin-1-oxyl top

Crystal data top

C₁₇H₂₅N₂O	F(000) = 596.00
M_r = 273.40	D_x = 1.154 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
a = 12.4422 (19) Å	Cell parameters from 24 reflections
b = 11.495 (3) Å	θ = 12.6–15.0°
c = 11.094 (2) Å	µ = 0.07 mm⁻¹
β = 97.381 (13)°	T = 100 K
V = 1573.6 (5) Å³	Plate, orange
Z = 4	0.40 × 0.40 × 0.10 mm

Data collection top

Rigaku AFC7R diffractometer	R_int = 0.017
Radiation source: Rigaku rotating anode	θ_max = 27.5°, θ_min = 2.4°
Graphite monochromator	h = −16→16
ω–2θ scans	k = −14→0
3796 measured reflections	l = 0→14
3611 independent reflections	3 standard reflections every 150 reflections
2992 reflections with I > 2σ(I)	intensity decay: 0.6%

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: difmap and geom
R[F² > 2σ(F²)] = 0.055	All H-atom parameters refined
wR(F²) = 0.165	Calculated w = 1/[σ²(F_o²) + (0.0592P)² + 1.6154P] where P = (F_o² + 2F_c²)/3
S = 1.13	(Δ/σ)_max = 0.007
3611 reflections	Δρ_max = 0.47 e Å⁻³
282 parameters	Δρ_min = −0.31 e Å⁻³
0 restraints	Extinction correction: SHELXL-97 (Sheldrick, 1997), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.007 (2)

Special details top

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
O1	0.47708 (11)	0.78360 (12)	0.14217 (12)	0.0255 (3)
N1	0.42109 (12)	0.71120 (13)	0.19716 (13)	0.0186 (3)
N2	0.23560 (13)	0.46947 (14)	0.37086 (14)	0.0220 (4)
C2	0.48362 (14)	0.61719 (16)	0.26835 (16)	0.0204 (4)
C3	0.41180 (15)	0.55299 (16)	0.34805 (16)	0.0199 (4)
C4	0.30014 (15)	0.52007 (16)	0.28271 (16)	0.0204 (4)
C5	0.24364 (15)	0.63096 (16)	0.23265 (16)	0.0206 (4)
C6	0.30457 (15)	0.69875 (16)	0.14455 (16)	0.0199 (4)
C7	0.22959 (15)	0.35961 (17)	0.37574 (16)	0.0212 (4)
C11	0.16685 (14)	0.29946 (16)	0.46046 (16)	0.0200 (4)
C12	0.10796 (16)	0.35985 (18)	0.53973 (18)	0.0248 (4)
C13	0.04808 (17)	0.30089 (19)	0.61674 (18)	0.0272 (4)
C14	0.04456 (14)	0.17910 (18)	0.61830 (17)	0.0233 (4)
C15	0.10319 (16)	0.11921 (17)	0.53939 (19)	0.0252 (4)
C16	0.16343 (16)	0.17822 (18)	0.46109 (19)	0.0251 (4)
C17	−0.01952 (17)	0.1150 (2)	0.7033 (2)	0.0291 (5)
C21	0.53044 (17)	0.53498 (19)	0.17904 (19)	0.0270 (4)
C22	0.57665 (17)	0.6747 (2)	0.35070 (19)	0.0289 (5)
C61	0.29865 (17)	0.63899 (19)	0.01955 (17)	0.0256 (4)
C62	0.25623 (17)	0.82115 (18)	0.12750 (19)	0.0266 (4)
H4	0.3066 (18)	0.463 (2)	0.215 (2)	0.023 (5)*
H7	0.267 (2)	0.306 (2)	0.321 (2)	0.040 (7)*
H12	0.110 (2)	0.444 (2)	0.537 (2)	0.034 (7)*
H13	0.003 (2)	0.346 (3)	0.670 (3)	0.054 (8)*
H15	0.100 (2)	0.034 (2)	0.540 (2)	0.038 (7)*
H16	0.207 (2)	0.133 (2)	0.405 (3)	0.043 (7)*
H21	0.473 (2)	0.488 (2)	0.128 (2)	0.035 (7)*
H22	0.578 (2)	0.480 (3)	0.226 (3)	0.045 (8)*
H23	0.573 (2)	0.580 (2)	0.125 (3)	0.042 (7)*
H24	0.5499 (19)	0.732 (2)	0.405 (2)	0.029 (6)*
H25	0.6158 (19)	0.614 (2)	0.400 (2)	0.028 (6)*
H26	0.628 (2)	0.720 (2)	0.302 (3)	0.043 (7)*
H31	0.4001 (19)	0.601 (2)	0.419 (2)	0.031 (6)*
H32	0.4475 (18)	0.483 (2)	0.379 (2)	0.020 (5)*
H51	0.1723 (18)	0.6128 (19)	0.1907 (19)	0.018 (5)*
H52	0.236 (2)	0.683 (2)	0.302 (2)	0.033 (6)*
H61	0.3154 (17)	0.558 (2)	0.0284 (19)	0.016 (5)*
H62	0.225 (2)	0.645 (2)	−0.022 (2)	0.031 (6)*
H63	0.350 (2)	0.680 (2)	−0.030 (2)	0.035 (7)*
H64	0.181 (2)	0.812 (2)	0.091 (2)	0.032 (6)*
H65	0.292 (2)	0.868 (2)	0.069 (3)	0.044 (7)*
H66	0.263 (2)	0.859 (2)	0.208 (2)	0.033 (6)*
H71	−0.042 (4)	0.165 (4)	0.761 (4)	0.110 (16)*
H72	−0.081 (3)	0.080 (4)	0.665 (4)	0.091 (13)*
H73	0.021 (3)	0.058 (3)	0.754 (3)	0.069 (10)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0270 (7)	0.0240 (7)	0.0262 (7)	−0.0067 (5)	0.0065 (5)	0.0051 (5)
N1	0.0213 (7)	0.0175 (7)	0.0174 (7)	−0.0041 (6)	0.0034 (6)	0.0020 (6)
N2	0.0244 (8)	0.0231 (8)	0.0186 (7)	−0.0039 (6)	0.0037 (6)	0.0007 (6)
C2	0.0205 (9)	0.0231 (9)	0.0172 (8)	0.0003 (7)	0.0007 (6)	0.0022 (7)
C3	0.0230 (9)	0.0203 (9)	0.0162 (8)	0.0010 (7)	0.0021 (7)	0.0020 (7)
C4	0.0262 (9)	0.0185 (9)	0.0164 (8)	−0.0039 (7)	0.0031 (7)	0.0007 (7)
C5	0.0212 (9)	0.0216 (9)	0.0183 (8)	−0.0035 (7)	0.0002 (7)	0.0008 (7)
C6	0.0224 (9)	0.0201 (9)	0.0166 (8)	−0.0009 (7)	0.0000 (7)	0.0012 (6)
C7	0.0217 (9)	0.0229 (9)	0.0188 (8)	−0.0005 (7)	0.0016 (7)	0.0016 (7)
C11	0.0180 (8)	0.0229 (9)	0.0187 (8)	−0.0010 (7)	0.0007 (6)	0.0024 (7)
C12	0.0280 (10)	0.0215 (9)	0.0260 (9)	−0.0028 (7)	0.0079 (7)	−0.0017 (7)
C13	0.0280 (10)	0.0305 (11)	0.0241 (9)	−0.0024 (8)	0.0073 (8)	−0.0002 (8)
C14	0.0172 (8)	0.0310 (10)	0.0212 (9)	0.0001 (7)	0.0000 (7)	0.0065 (7)
C15	0.0228 (9)	0.0207 (9)	0.0334 (10)	0.0025 (7)	0.0080 (8)	0.0077 (8)
C16	0.0234 (9)	0.0241 (10)	0.0289 (10)	0.0021 (7)	0.0078 (7)	0.0049 (8)
C17	0.0238 (10)	0.0378 (12)	0.0259 (10)	−0.0020 (9)	0.0037 (8)	0.0100 (9)
C21	0.0281 (10)	0.0299 (10)	0.0245 (9)	0.0083 (8)	0.0095 (8)	0.0033 (8)
C22	0.0239 (10)	0.0393 (12)	0.0222 (9)	−0.0064 (9)	−0.0016 (8)	0.0040 (9)
C61	0.0310 (10)	0.0280 (10)	0.0167 (9)	−0.0045 (8)	−0.0013 (7)	0.0003 (7)
C62	0.0281 (10)	0.0258 (10)	0.0261 (10)	0.0039 (8)	0.0036 (8)	0.0057 (8)

Geometric parameters (Å, º) top

O1—N1	1.2881 (19)	C12—H12	0.97 (3)
N1—C2	1.496 (2)	C13—C14	1.401 (3)
N1—C6	1.498 (2)	C13—H13	1.00 (3)
N2—C4	1.463 (2)	C14—C15	1.392 (3)
N2—C7	1.267 (3)	C14—C17	1.504 (3)
C2—C3	1.526 (2)	C15—C16	1.394 (3)
C2—C22	1.530 (3)	C15—H15	0.98 (3)
C2—C21	1.537 (3)	C16—H16	1.02 (3)
C3—C4	1.530 (3)	C17—H71	0.93 (5)
C3—H31	0.99 (3)	C17—H72	0.91 (4)
C3—H32	0.96 (2)	C17—H73	0.96 (4)
C4—C5	1.526 (3)	C21—H21	1.01 (3)
C4—H4	1.01 (2)	C21—H22	0.97 (3)
C5—C6	1.526 (2)	C21—H23	1.00 (3)
C5—H51	0.97 (2)	C22—H24	0.98 (3)
C5—H52	0.99 (3)	C22—H25	0.98 (3)
C6—C62	1.532 (3)	C22—H26	1.03 (3)
C6—C61	1.541 (3)	C61—H61	0.95 (2)
C7—C11	1.469 (2)	C61—H62	0.98 (3)
C7—H7	1.02 (3)	C61—H63	1.01 (3)
C11—C16	1.394 (3)	C62—H64	0.98 (3)
C11—C12	1.399 (3)	C62—H65	1.00 (3)
C12—C13	1.381 (3)	C62—H66	0.99 (3)

O1···O1ⁱ	5.6006 (11)	O1···H32ⁱⁱ	2.50 (2)
O1···O1ⁱⁱ	6.2237 (17)	O1···H22ⁱⁱ	2.82 (3)
O1···O1ⁱⁱⁱ	5.958 (3)	O1···H24^iv	2.89 (2)
O1···C3ⁱⁱ	3.387 (3)	O1···H31^iv	2.86 (3)
O1···C21ⁱⁱ	3.513 (3)

O1—N1—C2	116.13 (14)	C12—C13—C14	121.21 (19)
O1—N1—C6	115.62 (14)	C12—C13—H13	119.6 (18)
C2—N1—C6	123.23 (14)	C14—C13—H13	119.1 (18)
C7—N2—C4	117.73 (16)	C15—C14—C13	117.83 (18)
N1—C2—C3	110.59 (14)	C15—C14—C17	121.01 (19)
N1—C2—C22	107.78 (16)	C13—C14—C17	121.15 (19)
C3—C2—C22	108.52 (15)	C14—C15—C16	121.23 (18)
N1—C2—C21	108.55 (14)	C14—C15—H15	118.0 (15)
C3—C2—C21	112.01 (16)	C16—C15—H15	120.8 (15)
C22—C2—C21	109.30 (16)	C15—C16—C11	120.57 (18)
C2—C3—C4	114.14 (14)	C15—C16—H16	119.9 (16)
C2—C3—H31	110.2 (14)	C11—C16—H16	119.5 (16)
C4—C3—H31	107.4 (14)	C14—C17—H71	111 (3)
C2—C3—H32	109.6 (13)	C14—C17—H72	114 (3)
C4—C3—H32	108.3 (13)	H71—C17—H72	106 (4)
H31—C3—H32	106.9 (19)	C14—C17—H73	115 (2)
N2—C4—C5	107.98 (15)	H71—C17—H73	102 (3)
N2—C4—C3	108.94 (14)	H72—C17—H73	108 (3)
C5—C4—C3	108.29 (15)	C2—C21—H21	113.2 (15)
N2—C4—H4	109.7 (13)	C2—C21—H22	107.9 (17)
C5—C4—H4	110.7 (13)	H21—C21—H22	107 (2)
C3—C4—H4	111.1 (13)	C2—C21—H23	110.4 (16)
C4—C5—C6	114.61 (15)	H21—C21—H23	109 (2)
C4—C5—H51	110.2 (13)	H22—C21—H23	109 (2)
C6—C5—H51	107.6 (13)	C2—C22—H24	111.6 (14)
C4—C5—H52	107.8 (15)	C2—C22—H25	107.9 (14)
C6—C5—H52	107.4 (14)	H24—C22—H25	109 (2)
H51—C5—H52	109.2 (19)	C2—C22—H26	112.3 (16)
N1—C6—C5	109.56 (14)	H24—C22—H26	105 (2)
N1—C6—C62	107.77 (15)	H25—C22—H26	111 (2)
C5—C6—C62	109.19 (16)	C6—C61—H61	110.9 (13)
N1—C6—C61	108.97 (15)	C6—C61—H62	108.9 (14)
C5—C6—C61	112.25 (16)	H61—C61—H62	107.0 (19)
C62—C6—C61	109.00 (16)	C6—C61—H63	108.8 (15)
N2—C7—C11	122.38 (18)	H61—C61—H63	111.7 (19)
N2—C7—H7	122.7 (15)	H62—C61—H63	109 (2)
C11—C7—H7	114.9 (15)	C6—C62—H64	107.1 (15)
C16—C11—C12	118.29 (17)	C6—C62—H65	112.1 (16)
C16—C11—C7	119.51 (17)	H64—C62—H65	106 (2)
C12—C11—C7	122.18 (17)	C6—C62—H66	107.8 (15)
C13—C12—C11	120.86 (19)	H64—C62—H66	113 (2)
C13—C12—H12	121.9 (15)	H65—C62—H66	111 (2)
C11—C12—H12	117.2 (15)

O1—N1—C2—C3	168.89 (14)	C2—N1—C6—C62	156.46 (16)
O1—N1—C6—C5	−168.33 (15)	O1—N1—C6—C61	68.50 (19)
C6—N1—C2—C3	−37.3 (2)	C2—N1—C6—C61	−85.39 (19)
C2—N1—C6—C5	37.8 (2)	C4—C5—C6—C62	−165.30 (16)
N1—C2—C3—C4	45.9 (2)	C4—C5—C6—C61	73.7 (2)
C4—C5—C6—N1	−47.5 (2)	C4—N2—C7—C11	−179.81 (15)
C2—C3—C4—C5	−57.4 (2)	N2—C7—C11—C16	179.90 (18)
C3—C4—C5—C6	58.64 (19)	N2—C7—C11—C12	1.2 (3)
C2—C3—C4—N2	−174.61 (15)	C16—C11—C12—C13	0.1 (3)
N2—C4—C5—C6	176.46 (14)	C7—C11—C12—C13	178.76 (18)
C7—N2—C4—C3	−98.95 (19)	C11—C12—C13—C14	0.2 (3)
C7—N2—C4—C5	143.65 (17)	C12—C13—C14—C15	−0.2 (3)
O1—N1—C2—C22	50.4 (2)	C12—C13—C14—C17	179.21 (19)
C6—N1—C2—C22	−155.80 (16)	C13—C14—C15—C16	−0.1 (3)
O1—N1—C2—C21	−67.8 (2)	C17—C14—C15—C16	−179.48 (19)
C6—N1—C2—C21	85.93 (19)	C14—C15—C16—C11	0.3 (3)
C22—C2—C3—C4	163.94 (17)	C12—C11—C16—C15	−0.3 (3)
C21—C2—C3—C4	−75.3 (2)	C7—C11—C16—C15	−179.06 (17)
O1—N1—C6—C62	−49.6 (2)

Symmetry codes: (i) x, −y+3/2, z+1/2; (ii) −x+1, y+1/2, −z+1/2; (iii) −x+1, −y+2, −z; (iv) x, −y+3/2, z−1/2.

(12) 4-(2-naphthylmethyleneamino)-2,2,6,6-tetramethylpiperidin-1-oxyl top

Crystal data top

C₂₀H₂₅N₂O	D_x = 1.189 Mg m⁻³
M_r = 309.43	Melting point: not measured K
Orthorhombic, Pna2₁	Mo Kα radiation, λ = 0.71073 Å
a = 20.0837 (19) Å	Cell parameters from 25 reflections
b = 5.6969 (7) Å	θ = 13.6–17.2°
c = 15.106 (2) Å	µ = 0.07 mm⁻¹
V = 1728.4 (4) Å³	T = 295 K
Z = 4	Prism, orange
F(000) = 668.00	0.50 × 0.38 × 0.10 mm

Data collection top

Rigaku AFC5R diffractometer	R_int = 0.000
Radiation source: Rigaku rotating anode	θ_max = 27.5°, θ_min = 2.7°
Graphite monochromator	h = 0→26
ω–2θ scans	k = 0→7
2059 measured reflections	l = 0→19
2059 independent reflections	3 standard reflections every 100 reflections
1491 reflections with I > 2σ(I)	intensity decay: 0.2%

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: difmap and geom
R[F² > 2σ(F²)] = 0.043	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.110	Calculated w = 1/[σ²(F_o²) + (0.0544P)² + 0.0293P] where P = (F_o² + 2F_c²)/3
S = 1.07	(Δ/σ)_max = 0.004
2059 reflections	Δρ_max = 0.16 e Å⁻³
260 parameters	Δρ_min = −0.13 e Å⁻³
0 restraints	Extinction correction: SHELXL-97 (Sheldrick, 1997), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.017 (2)

Special details top

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
O1	−0.09774 (12)	−0.3230 (4)	0.1012	0.0602 (7)
N1	−0.05695 (12)	−0.1653 (4)	0.0734 (2)	0.0430 (6)
N2	0.07109 (12)	0.3991 (4)	−0.0066 (2)	0.0439 (6)
C2	−0.01415 (14)	−0.0529 (5)	0.1420 (3)	0.0396 (7)
C3	0.04118 (15)	0.0899 (6)	0.0980 (3)	0.0417 (7)
C4	0.01643 (15)	0.2424 (5)	0.0221 (3)	0.0397 (7)
C5	−0.01272 (18)	0.0808 (6)	−0.0477 (3)	0.0438 (7)
C6	−0.07313 (14)	−0.0602 (5)	−0.0148 (3)	0.0434 (7)
C7	0.09733 (15)	0.3735 (6)	−0.0819 (3)	0.0427 (7)
C11	0.14907 (14)	0.5293 (5)	−0.1170 (3)	0.0393 (7)
C12	0.17172 (15)	0.4933 (6)	−0.2009 (3)	0.0435 (7)
C13	0.21842 (14)	0.6465 (6)	−0.2413 (3)	0.0408 (7)
C14	0.24184 (14)	0.8406 (6)	−0.1928 (3)	0.0447 (7)
C15	0.21882 (17)	0.8718 (7)	−0.1045 (3)	0.0508 (8)
C16	0.17416 (16)	0.7218 (6)	−0.0684 (3)	0.0488 (8)
C17	0.24120 (17)	0.6118 (8)	−0.3288 (3)	0.0540 (9)
C18	0.28408 (17)	0.7677 (8)	−0.3670 (3)	0.0632 (11)
C19	0.30683 (18)	0.9607 (8)	−0.3193 (3)	0.0639 (11)
C20	0.28659 (18)	0.9984 (8)	−0.2347 (3)	0.0570 (9)
C21	0.01701 (17)	−0.2516 (6)	0.1962 (3)	0.0503 (8)
C22	−0.05755 (17)	0.1012 (6)	0.2019 (3)	0.0526 (8)
C61	−0.13571 (16)	0.0933 (6)	−0.0053 (3)	0.0636 (10)
C62	−0.0870 (2)	−0.2606 (6)	−0.0789 (3)	0.0608 (10)
H4	−0.0188 (14)	0.356 (5)	0.047 (2)	0.039 (8)*
H7	0.0861 (16)	0.249 (6)	−0.120 (2)	0.045 (9)*
H12	0.1555 (14)	0.370 (5)	−0.235 (2)	0.036 (7)*
H15	0.2316 (15)	1.005 (6)	−0.076 (2)	0.045 (9)*
H16	0.1606 (18)	0.749 (7)	−0.010 (3)	0.073 (12)*
H17	0.2256 (17)	0.481 (7)	−0.355 (3)	0.063 (12)*
H18	0.2997 (19)	0.736 (7)	−0.423 (3)	0.068 (11)*
H19	0.3379 (19)	1.062 (8)	−0.342 (3)	0.072 (12)*
H20	0.2995 (19)	1.127 (8)	−0.205 (3)	0.070 (13)*
H21	0.0375	−0.3617	0.1583	0.058*
H22	−0.0177	−0.3297	0.2291	0.058*
H23	0.0484	−0.1898	0.2367	0.058*
H24	−0.0322	0.1541	0.2517	0.063*
H25	−0.0736	0.2331	0.1703	0.063*
H26	−0.0947	0.0123	0.2234	0.063*
H31	0.0605 (17)	0.194 (7)	0.142 (3)	0.060 (10)*
H32	0.0761 (15)	−0.011 (6)	0.074 (2)	0.048 (9)*
H51	0.0240 (15)	−0.027 (5)	−0.069 (2)	0.037 (8)*
H52	−0.0267 (15)	0.156 (6)	−0.096 (2)	0.047 (9)*
H61	−0.1455	0.1644	−0.0630	0.075*
H62	−0.1275	0.2168	0.0348	0.075*
H63	−0.1722	0.0034	0.0118	0.075*
H64	−0.0495	−0.3620	−0.0818	0.070*
H65	−0.1248	−0.3463	−0.0599	0.070*
H66	−0.0954	−0.1991	−0.1369	0.070*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0635 (14)	0.0501 (12)	0.0670 (15)	−0.0179 (11)	0.0085 (13)	0.0168 (12)
N1	0.0454 (13)	0.0367 (12)	0.0468 (14)	−0.0043 (11)	0.0053 (12)	0.0046 (12)
N2	0.0455 (13)	0.0456 (14)	0.0406 (14)	−0.0090 (12)	0.0042 (11)	0.0042 (13)
C2	0.0445 (15)	0.0384 (16)	0.0358 (14)	−0.0011 (13)	0.0037 (13)	0.0029 (13)
C3	0.0384 (15)	0.0467 (17)	0.0398 (16)	−0.0026 (14)	0.0009 (14)	0.0000 (15)
C4	0.0411 (15)	0.0425 (16)	0.0354 (14)	−0.0056 (15)	0.0035 (13)	0.0059 (14)
C5	0.0501 (18)	0.0455 (18)	0.0358 (16)	−0.0069 (16)	−0.0020 (14)	0.0071 (15)
C6	0.0402 (15)	0.0422 (16)	0.0478 (17)	−0.0073 (14)	−0.0042 (14)	0.0101 (15)
C7	0.0439 (16)	0.0445 (17)	0.0397 (16)	−0.0056 (14)	0.0010 (14)	0.0021 (15)
C11	0.0373 (15)	0.0423 (16)	0.0382 (15)	−0.0008 (13)	0.0013 (12)	0.0052 (14)
C12	0.0414 (16)	0.0470 (17)	0.0421 (16)	−0.0087 (14)	−0.0004 (14)	−0.0021 (16)
C13	0.0334 (13)	0.0463 (17)	0.0427 (15)	0.0008 (13)	0.0004 (13)	0.0095 (15)
C14	0.0352 (14)	0.0495 (18)	0.0492 (18)	−0.0030 (14)	−0.0011 (13)	0.0064 (16)
C15	0.0499 (18)	0.0488 (19)	0.054 (2)	−0.0120 (16)	0.0021 (16)	−0.0065 (17)
C16	0.0494 (18)	0.055 (2)	0.0419 (18)	−0.0033 (16)	0.0064 (15)	−0.0034 (16)
C17	0.0469 (17)	0.073 (2)	0.0426 (17)	−0.0083 (18)	0.0063 (15)	0.0002 (19)
C18	0.0455 (18)	0.097 (3)	0.047 (2)	−0.008 (2)	0.0092 (16)	0.010 (2)
C19	0.0441 (18)	0.081 (3)	0.066 (3)	−0.0183 (19)	0.0062 (18)	0.024 (2)
C20	0.0495 (19)	0.061 (2)	0.060 (2)	−0.0123 (18)	0.0004 (18)	0.009 (2)
C21	0.062 (2)	0.0465 (18)	0.0423 (17)	0.0064 (16)	0.0030 (16)	0.0103 (16)
C22	0.063 (2)	0.0438 (18)	0.0511 (18)	0.0063 (16)	0.0190 (16)	0.0054 (16)
C61	0.0459 (17)	0.059 (2)	0.086 (3)	−0.0016 (17)	−0.0041 (19)	0.015 (2)
C62	0.068 (2)	0.055 (2)	0.059 (2)	−0.0221 (18)	−0.0164 (18)	0.0101 (19)

Geometric parameters (Å, º) top

O1—N1	1.286 (3)	C13—C17	1.412 (5)
N1—C2	1.491 (4)	C14—C20	1.421 (5)
N1—C6	1.497 (4)	C14—C15	1.423 (5)
N2—C4	1.480 (4)	C15—C16	1.353 (5)
N2—C7	1.262 (4)	C15—H15	0.91 (3)
C2—C3	1.530 (4)	C16—H16	0.93 (4)
C2—C21	1.531 (4)	C17—C18	1.365 (5)
C2—C22	1.533 (4)	C17—H17	0.90 (4)
C3—C4	1.521 (4)	C18—C19	1.392 (6)
C3—H31	0.98 (4)	C18—H18	0.92 (4)
C3—H32	0.98 (3)	C19—C20	1.358 (6)
C4—C5	1.518 (4)	C19—H19	0.91 (4)
C4—H4	1.03 (3)	C20—H20	0.90 (4)
C5—C6	1.538 (4)	C21—H21	0.944 (4)
C5—H51	1.01 (3)	C21—H22	0.965 (4)
C5—H52	0.89 (4)	C21—H23	0.946 (4)
C6—C62	1.523 (5)	C22—H24	0.957 (4)
C6—C61	1.538 (4)	C22—H25	0.947 (4)
C7—C11	1.466 (4)	C22—H26	0.958 (3)
C7—H7	0.94 (3)	C61—H61	0.982 (5)
C11—C12	1.362 (4)	C61—H62	0.943 (4)
C11—C16	1.412 (4)	C61—H63	0.930 (3)
C12—C13	1.419 (4)	C62—H64	0.950 (4)
C12—H12	0.93 (3)	C62—H65	0.948 (4)
C13—C14	1.407 (4)	C62—H66	0.959 (4)

O1···O1ⁱ	5.6969 (7)	O1···C61ⁱ	3.772 (5)
O1···O1ⁱⁱ	8.748 (3)	O1···H4ⁱ	2.56 (3)
O1···C4ⁱ	3.580 (4)	O1···H25ⁱ	2.78 (2)
O1···C12ⁱⁱⁱ	3.477 (4)	O1···H62ⁱ	2.87 (2)
O1···C17ⁱⁱⁱ	3.483 (4)	O1···H12ⁱⁱⁱ	2.75 (3)
O1···C22ⁱ	3.705 (4)	O1···H17ⁱⁱⁱ	2.80 (4)

O1—N1—C2	116.2 (2)	C13—C14—C20	118.5 (3)
O1—N1—C6	115.6 (2)	C13—C14—C15	118.6 (3)
C2—N1—C6	124.9 (2)	C20—C14—C15	123.0 (3)
C7—N2—C4	120.3 (3)	C16—C15—C14	120.9 (3)
N1—C2—C3	110.2 (2)	C16—C15—H15	121 (2)
N1—C2—C21	106.8 (2)	C14—C15—H15	117 (2)
C3—C2—C21	109.2 (2)	C15—C16—C11	121.2 (3)
N1—C2—C22	109.2 (2)	C15—C16—H16	118 (2)
C3—C2—C22	111.4 (3)	C11—C16—H16	121 (2)
C21—C2—C22	109.9 (3)	C18—C17—C13	120.6 (4)
C4—C3—C2	113.2 (2)	C18—C17—H17	125 (2)
C4—C3—H31	107 (2)	C13—C17—H17	114 (2)
C2—C3—H31	108 (2)	C17—C18—C19	120.2 (4)
C4—C3—H32	107 (2)	C17—C18—H18	118 (3)
C2—C3—H32	111.7 (18)	C19—C18—H18	121 (3)
H31—C3—H32	109 (3)	C20—C19—C18	120.9 (4)
N2—C4—C5	116.6 (2)	C20—C19—H19	117 (3)
N2—C4—C3	108.8 (2)	C18—C19—H19	122 (3)
C5—C4—C3	107.7 (2)	C19—C20—C14	120.6 (4)
N2—C4—H4	103.9 (15)	C19—C20—H20	121 (3)
C5—C4—H4	111.8 (16)	C14—C20—H20	118 (3)
C3—C4—H4	107.7 (17)	C2—C21—H21	110.2 (3)
C4—C5—C6	113.3 (3)	C2—C21—H22	108.8 (3)
C4—C5—H51	108.1 (16)	H21—C21—H22	108.8 (3)
C6—C5—H51	111.3 (16)	C2—C21—H23	110.0 (3)
C4—C5—H52	114 (2)	H21—C21—H23	110.4 (3)
C6—C5—H52	106 (2)	H22—C21—H23	108.6 (4)
H51—C5—H52	105 (3)	C2—C22—H24	110.0 (3)
N1—C6—C62	107.8 (2)	C2—C22—H25	110.5 (3)
N1—C6—C5	109.0 (2)	H24—C22—H25	109.2 (4)
C62—C6—C5	109.3 (3)	C2—C22—H26	109.9 (3)
N1—C6—C61	108.7 (3)	H24—C22—H26	108.2 (4)
C62—C6—C61	109.7 (3)	H25—C22—H26	109.0 (3)
C5—C6—C61	112.2 (3)	C6—C61—H61	108.4 (4)
N2—C7—C11	123.5 (3)	C6—C61—H62	109.9 (3)
N2—C7—H7	122.7 (19)	H61—C61—H62	107.4 (3)
C11—C7—H7	113.8 (19)	C6—C61—H63	110.9 (3)
C12—C11—C16	118.8 (3)	H61—C61—H63	108.4 (4)
C12—C11—C7	118.8 (3)	H62—C61—H63	111.8 (5)
C16—C11—C7	122.4 (3)	C6—C62—H64	109.9 (3)
C11—C12—C13	121.9 (3)	C6—C62—H65	109.8 (4)
C11—C12—H12	120.7 (19)	H64—C62—H65	109.6 (4)
C13—C12—H12	117.4 (19)	C6—C62—H66	109.8 (3)
C14—C13—C17	119.3 (3)	H64—C62—H66	108.8 (5)
C14—C13—C12	118.7 (3)	H65—C62—H66	108.9 (4)
C17—C13—C12	122.1 (3)

O1—N1—C2—C3	168.0 (2)	C4—N2—C7—C11	176.6 (3)
O1—N1—C6—C5	−167.4 (3)	N2—C7—C11—C12	−176.7 (3)
C6—N1—C2—C3	−33.8 (4)	N2—C7—C11—C16	0.4 (5)
C2—N1—C6—C5	34.2 (4)	C16—C11—C12—C13	−1.5 (5)
N1—C2—C3—C4	45.7 (3)	C7—C11—C12—C13	175.7 (3)
C4—C5—C6—N1	−47.2 (4)	C11—C12—C13—C14	0.1 (4)
C2—C3—C4—C5	−61.3 (3)	C11—C12—C13—C17	−179.0 (3)
C3—C4—C5—C6	62.5 (4)	C17—C13—C14—C20	1.5 (4)
C2—C3—C4—N2	171.4 (3)	C12—C13—C14—C20	−177.6 (3)
N2—C4—C5—C6	−174.9 (3)	C17—C13—C14—C15	−179.5 (3)
C7—N2—C4—C3	112.6 (3)	C12—C13—C14—C15	1.4 (4)
C7—N2—C4—C5	−9.4 (4)	C13—C14—C15—C16	−1.6 (5)
O1—N1—C2—C21	49.5 (3)	C20—C14—C15—C16	177.4 (3)
C6—N1—C2—C21	−152.3 (3)	C14—C15—C16—C11	0.2 (5)
O1—N1—C2—C22	−69.4 (3)	C12—C11—C16—C15	1.4 (5)
C6—N1—C2—C22	88.9 (3)	C7—C11—C16—C15	−175.7 (3)
C21—C2—C3—C4	162.7 (3)	C14—C13—C17—C18	−1.7 (5)
C22—C2—C3—C4	−75.6 (3)	C12—C13—C17—C18	177.3 (3)
O1—N1—C6—C62	−48.9 (3)	C13—C17—C18—C19	1.2 (6)
C2—N1—C6—C62	152.8 (3)	C17—C18—C19—C20	−0.5 (6)
O1—N1—C6—C61	70.0 (3)	C18—C19—C20—C14	0.3 (6)
C2—N1—C6—C61	−88.4 (3)	C13—C14—C20—C19	−0.8 (5)
C4—C5—C6—C62	−164.8 (3)	C15—C14—C20—C19	−179.8 (3)
C4—C5—C6—C61	73.3 (4)

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

(13) 4-(4-phenoxyphenylmethyleneamino)-2,2,6,6-tetramethylpiperidin-1-oxyl top

Crystal data top

C₂₂H₂₇N₂O₂	D_x = 1.157 Mg m⁻³
M_r = 351.47	Melting point: not measured K
Orthorhombic, Pca2₁	Mo Kα radiation, λ = 0.71073 Å
a = 30.565 (9) Å	Cell parameters from 25 reflections
b = 5.993 (2) Å	θ = 14.2–17.2°
c = 22.032 (5) Å	µ = 0.07 mm⁻¹
V = 4036 (2) Å³	T = 297 K
Z = 8	Needle, orange
F(000) = 1512.00	0.70 × 0.50 × 0.40 mm

Data collection top

Rigaku AFC4 diffractometer	R_int = 0.000
Radiation source: fine-focus sealed tube	θ_max = 27.5°, θ_min = 1.3°
Graphite monochromator	h = 0→39
ω–2θ scans	k = 0→7
4763 measured reflections	l = −28→0
4763 independent reflections	3 standard reflections every 50 reflections
2517 reflections with I > 2σ(I)	intensity decay: 0.0%

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.059	Hydrogen site location: difmap and geom
wR(F²) = 0.124	H atoms treated by a mixture of independent and constrained refinement
S = 0.97	Calculated w = 1/[σ²(F_o²) + (0.0471P)²] where P = (F_o² + 2F_c²)/3
4763 reflections	(Δ/σ)_max = 0.001
468 parameters	Δρ_max = 0.16 e Å⁻³
0 restraints	Δρ_min = −0.16 e Å⁻³

Special details top

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
O1A	0.28562 (10)	1.1004 (5)	0.5908	0.0808 (10)
O2A	0.50583 (10)	0.1062 (5)	0.25169 (18)	0.0712 (9)
N1A	0.30453 (10)	0.9470 (5)	0.56088 (19)	0.0510 (9)
N2A	0.37560 (12)	0.5370 (5)	0.4439 (2)	0.0655 (10)
C2A	0.34251 (12)	0.8331 (7)	0.5894 (2)	0.0524 (10)
C3A	0.37044 (12)	0.7267 (6)	0.5394 (2)	0.0551 (11)
H31A	0.3965	0.6464	0.5592	0.055*
H32A	0.3852	0.8506	0.5165	0.055*
C4A	0.34539 (13)	0.5962 (6)	0.4928 (2)	0.0519 (11)
H4A	0.3327	0.4638	0.5093	0.052*
C5A	0.30986 (14)	0.7386 (7)	0.4647 (2)	0.0582 (11)
H51A	0.3239	0.8515	0.4389	0.058*
H52A	0.2938	0.6655	0.4321	0.058*
C6A	0.27820 (13)	0.8489 (7)	0.5096 (2)	0.0548 (10)
C7A	0.38865 (13)	0.3412 (6)	0.4382 (2)	0.0516 (10)
H7A	0.3794	0.2324	0.4660	0.052*
C11A	0.42016 (12)	0.2741 (6)	0.3901 (2)	0.0494 (10)
C12A	0.43834 (13)	0.0638 (6)	0.3888 (2)	0.0543 (11)
H12A	0.4299	−0.0327	0.4177	0.054*
C13A	0.46770 (13)	0.0002 (6)	0.3445 (2)	0.0544 (11)
H13A	0.4816	−0.1849	0.3446	0.054*
C14A	0.47874 (13)	0.1514 (7)	0.2991 (2)	0.0536 (11)
C15A	0.45981 (16)	0.3623 (7)	0.2987 (2)	0.0658 (13)
H15A	0.4677	0.4555	0.2654	0.066*
C16A	0.43064 (14)	0.4204 (7)	0.3432 (3)	0.0622 (12)
H16A	0.4179	0.5490	0.3400	0.062*
C21A	0.36960 (16)	1.0082 (8)	0.6232 (3)	0.0820 (15)
H21A	0.4014	0.9407	0.6395	0.082*
H22A	0.3788	1.1095	0.5946	0.082*
H23A	0.3549	1.0658	0.6534	0.082*
C22A	0.32611 (15)	0.6592 (8)	0.6341 (2)	0.0710 (13)
H24A	0.3514	0.6023	0.6544	0.071*
H25A	0.3109	0.5163	0.6170	0.071*
H26A	0.3032	0.7268	0.6593	0.071*
C41A	0.53273 (13)	−0.0840 (6)	0.2540 (2)	0.0523 (10)
C42A	0.56344 (16)	−0.1073 (9)	0.2976 (2)	0.0720 (14)
H42A	0.5627	0.0229	0.3311	0.072*
C43A	0.58994 (16)	−0.2887 (11)	0.2969 (3)	0.0891 (17)
H43A	0.6080	−0.2985	0.3274	0.089*
C44A	0.58517 (19)	−0.4503 (9)	0.2532 (3)	0.0910 (18)
H44A	0.6021	−0.5739	0.2538	0.091*
C45A	0.55483 (19)	−0.4210 (8)	0.2084 (3)	0.0795 (15)
H45A	0.5520	−0.5360	0.1734	0.080*
C46A	0.52761 (13)	−0.2394 (7)	0.2090 (2)	0.0588 (11)
H46A	0.5076	−0.2077	0.1837	0.059*
C61A	0.24522 (14)	0.6816 (8)	0.5353 (2)	0.0716 (13)
H61A	0.2250	0.7436	0.5736	0.072*
H62A	0.2586	0.5557	0.5591	0.072*
H63A	0.2248	0.6375	0.5070	0.072*
C62A	0.25424 (16)	1.0416 (7)	0.4783 (3)	0.0785 (14)
H64A	0.2745	1.1452	0.4632	0.078*
H65A	0.2371	0.9782	0.4465	0.078*
H66A	0.2282	1.1152	0.5053	0.078*
O1B	0.03803 (11)	1.5295 (5)	0.60404 (19)	0.0901 (11)
O2B	0.25303 (12)	0.5180 (5)	0.25981 (19)	0.0829 (10)
N1B	0.05678 (11)	1.3859 (5)	0.57138 (19)	0.0536 (9)
N2B	0.12416 (11)	0.9660 (5)	0.45141 (19)	0.0550 (9)
C2B	0.09636 (12)	1.2726 (6)	0.5976 (2)	0.0516 (10)
C3B	0.12246 (12)	1.1666 (6)	0.5453 (2)	0.0509 (10)
H31B	0.1466	1.0780	0.5573	0.051*
H32B	0.1358	1.2788	0.5214	0.051*
C4B	0.09527 (12)	1.0281 (6)	0.5015 (2)	0.0514 (10)
H4B	0.0830	0.8835	0.5295	0.051*
C5B	0.05883 (14)	1.1692 (7)	0.4757 (2)	0.0601 (11)
H51B	0.0714	1.2765	0.4524	0.060*
H52B	0.0400	1.0793	0.4434	0.060*
C6B	0.02950 (12)	1.2784 (7)	0.5229 (2)	0.0553 (11)
C7B	0.13438 (12)	0.7632 (6)	0.4430 (2)	0.0476 (10)
H7B	0.1244	0.6459	0.4699	0.048*
C11B	0.16404 (12)	0.6912 (6)	0.3941 (2)	0.0474 (10)
C12B	0.18171 (12)	0.4781 (6)	0.3942 (2)	0.0496 (10)
H12B	0.1704	0.3510	0.4278	0.050*
C13B	0.21172 (13)	0.4157 (6)	0.3505 (2)	0.0513 (10)
H13B	0.2260	0.2853	0.3519	0.051*
C14B	0.22453 (13)	0.5648 (7)	0.3063 (2)	0.0546 (11)
C15B	0.20540 (15)	0.7761 (7)	0.3049 (2)	0.0658 (12)
H15B	0.2127	0.8696	0.2729	0.066*
C16B	0.17615 (13)	0.8363 (6)	0.3485 (2)	0.0538 (11)
H16B	0.1594	0.9776	0.3443	0.054*
C21B	0.12413 (15)	1.4547 (7)	0.6274 (3)	0.0751 (14)
H21B	0.1511	1.4138	0.6424	0.075*
H22B	0.1309	1.5744	0.6034	0.075*
H23B	0.1007	1.5499	0.6635	0.075*
C22B	0.08288 (16)	1.1055 (8)	0.6450 (3)	0.0771 (14)
H24B	0.1043	0.0431	0.6645	0.077*
H25B	0.0663	0.9792	0.6275	0.077*
H26B	0.0574	1.1652	0.6779	0.077*
C41B	0.27666 (15)	0.3195 (8)	0.2584 (3)	0.0633 (12)
C42B	0.30733 (17)	0.2689 (9)	0.3023 (3)	0.0814 (15)
H42B	0.3105	0.3803	0.3308	0.081*
C43B	0.33094 (16)	0.0747 (10)	0.2971 (3)	0.0912 (17)
H43B	0.3522	0.0644	0.3299	0.091*
C44B	0.32445 (17)	−0.0652 (9)	0.2499 (3)	0.0828 (15)
H44B	0.3412	−0.2251	0.2508	0.083*
C45B	0.29440 (18)	−0.0108 (9)	0.2069 (3)	0.0797 (15)
H45B	0.2927	−0.1125	0.1731	0.080*
C46B	0.27032 (14)	0.1813 (8)	0.2110 (2)	0.0674 (13)
H46B	0.2516	0.2155	0.1840	0.067*
C61B	−0.00233 (14)	1.1093 (8)	0.5519 (3)	0.0728 (14)
H61B	−0.0166	1.1665	0.5944	0.073*
H62B	0.0121	0.9560	0.5623	0.073*
H63B	−0.0240	1.0713	0.5225	0.073*
C62B	0.00396 (17)	1.4662 (8)	0.4919 (3)	0.0848 (16)
H64B	0.0209	1.5890	0.4843	0.085*
H65B	−0.0196	1.3954	0.4628	0.085*
H66B	−0.0152	1.5278	0.5201	0.085*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1A	0.080 (2)	0.080 (2)	0.083 (2)	0.0257 (18)	−0.0040 (19)	−0.031 (2)
O2A	0.088 (2)	0.0659 (19)	0.0599 (19)	0.0224 (18)	0.0213 (17)	0.0049 (16)
N1A	0.049 (2)	0.053 (2)	0.051 (2)	0.0082 (17)	0.0027 (16)	−0.0146 (17)
N2A	0.079 (3)	0.0443 (19)	0.073 (3)	0.0045 (19)	0.028 (2)	−0.0060 (19)
C2A	0.050 (2)	0.059 (2)	0.049 (2)	0.002 (2)	−0.006 (2)	−0.011 (2)
C3A	0.052 (2)	0.057 (2)	0.057 (3)	0.006 (2)	−0.001 (2)	−0.007 (2)
C4A	0.056 (3)	0.045 (2)	0.055 (3)	−0.002 (2)	0.012 (2)	−0.006 (2)
C5A	0.070 (3)	0.059 (2)	0.046 (2)	−0.001 (2)	−0.002 (2)	−0.008 (2)
C6A	0.051 (2)	0.055 (2)	0.059 (3)	0.004 (2)	−0.007 (2)	−0.010 (2)
C7A	0.048 (2)	0.046 (2)	0.061 (3)	−0.0034 (19)	0.006 (2)	−0.004 (2)
C11A	0.048 (2)	0.050 (2)	0.050 (2)	−0.004 (2)	0.003 (2)	−0.006 (2)
C12A	0.055 (3)	0.047 (2)	0.061 (3)	0.008 (2)	0.005 (2)	0.004 (2)
C13A	0.053 (3)	0.051 (2)	0.060 (3)	0.004 (2)	0.009 (2)	−0.004 (2)
C14A	0.058 (3)	0.058 (3)	0.045 (2)	0.002 (2)	0.010 (2)	−0.007 (2)
C15A	0.084 (3)	0.044 (2)	0.069 (3)	0.009 (2)	0.026 (3)	0.007 (2)
C16A	0.065 (3)	0.040 (2)	0.081 (3)	0.004 (2)	0.010 (3)	−0.013 (2)
C21A	0.075 (3)	0.091 (4)	0.080 (3)	−0.012 (3)	−0.017 (3)	−0.022 (3)
C22A	0.082 (3)	0.078 (3)	0.053 (3)	0.015 (3)	−0.001 (2)	0.005 (3)
C41A	0.050 (2)	0.051 (2)	0.056 (3)	−0.001 (2)	0.014 (2)	0.004 (2)
C42A	0.074 (3)	0.088 (4)	0.054 (3)	0.007 (3)	−0.008 (3)	−0.010 (3)
C43A	0.065 (3)	0.122 (5)	0.081 (4)	0.015 (4)	−0.011 (3)	0.008 (4)
C44A	0.087 (4)	0.089 (4)	0.096 (4)	0.043 (3)	0.027 (4)	0.023 (4)
C45A	0.104 (4)	0.055 (3)	0.079 (4)	0.015 (3)	0.028 (3)	−0.016 (3)
C46A	0.065 (3)	0.068 (3)	0.043 (2)	0.003 (3)	0.005 (2)	−0.002 (2)
C61A	0.050 (3)	0.089 (3)	0.076 (3)	−0.004 (3)	−0.007 (2)	−0.006 (3)
C62A	0.071 (3)	0.072 (3)	0.093 (4)	0.020 (3)	−0.026 (3)	−0.004 (3)
O1B	0.088 (2)	0.083 (2)	0.100 (3)	0.029 (2)	−0.007 (2)	−0.041 (2)
O2B	0.108 (3)	0.075 (2)	0.065 (2)	0.012 (2)	0.0391 (19)	0.0026 (18)
N1B	0.056 (2)	0.047 (2)	0.058 (2)	0.0107 (17)	−0.0012 (18)	−0.0071 (18)
N2B	0.066 (2)	0.0462 (19)	0.052 (2)	0.0005 (18)	0.0119 (18)	−0.0026 (18)
C2B	0.053 (2)	0.048 (2)	0.054 (2)	0.000 (2)	−0.003 (2)	−0.004 (2)
C3B	0.047 (2)	0.049 (2)	0.056 (3)	0.005 (2)	0.002 (2)	0.007 (2)
C4B	0.051 (2)	0.047 (2)	0.056 (2)	0.003 (2)	0.012 (2)	0.003 (2)
C5B	0.066 (3)	0.057 (3)	0.057 (3)	0.007 (2)	−0.009 (2)	0.004 (2)
C6B	0.045 (2)	0.053 (2)	0.068 (3)	0.002 (2)	−0.008 (2)	−0.010 (2)
C7B	0.051 (2)	0.043 (2)	0.049 (2)	−0.009 (2)	0.004 (2)	0.003 (2)
C11B	0.052 (2)	0.045 (2)	0.045 (2)	−0.0053 (19)	0.000 (2)	−0.004 (2)
C12B	0.050 (2)	0.045 (2)	0.055 (3)	−0.008 (2)	0.009 (2)	−0.004 (2)
C13B	0.058 (3)	0.045 (2)	0.051 (2)	0.005 (2)	−0.001 (2)	−0.005 (2)
C14B	0.062 (3)	0.050 (3)	0.052 (3)	0.000 (2)	0.006 (2)	−0.002 (2)
C15B	0.086 (3)	0.064 (3)	0.048 (3)	−0.006 (3)	0.014 (3)	0.007 (2)
C16B	0.065 (3)	0.040 (2)	0.056 (3)	0.000 (2)	0.005 (2)	−0.001 (2)
C21B	0.069 (3)	0.066 (3)	0.090 (4)	−0.007 (3)	−0.023 (3)	−0.010 (3)
C22B	0.088 (4)	0.084 (3)	0.059 (3)	0.001 (3)	0.006 (3)	0.008 (3)
C41B	0.062 (3)	0.072 (3)	0.056 (3)	0.000 (3)	0.014 (2)	−0.008 (3)
C42B	0.082 (3)	0.090 (4)	0.072 (3)	−0.008 (3)	0.002 (3)	−0.028 (3)
C43B	0.057 (3)	0.123 (5)	0.093 (4)	0.010 (3)	−0.010 (3)	−0.009 (4)
C44B	0.068 (3)	0.085 (4)	0.096 (4)	0.010 (3)	0.017 (3)	−0.009 (4)
C45B	0.091 (4)	0.077 (4)	0.071 (3)	−0.015 (3)	0.024 (3)	−0.028 (3)
C46B	0.064 (3)	0.083 (3)	0.055 (3)	−0.006 (3)	0.004 (2)	−0.004 (3)
C61B	0.051 (3)	0.077 (3)	0.090 (4)	0.000 (3)	−0.001 (3)	−0.020 (3)
C62B	0.077 (3)	0.066 (3)	0.112 (4)	0.022 (3)	−0.033 (3)	−0.011 (3)

Geometric parameters (Å, º) top

O1A—N1A	1.270 (4)	O1B—N1B	1.260 (4)
O2A—C14A	1.361 (5)	O2B—C14B	1.374 (5)
O2A—C41A	1.407 (5)	O2B—C41B	1.392 (5)
N1A—C2A	1.486 (5)	N1B—C2B	1.502 (5)
N1A—C6A	1.507 (5)	N1B—C6B	1.501 (5)
N2A—C4A	1.464 (5)	N2B—C4B	1.462 (5)
N2A—C7A	1.246 (5)	N2B—C7B	1.268 (4)
C2A—C3A	1.531 (5)	C2B—C22B	1.505 (6)
C2A—C21A	1.531 (6)	C2B—C21B	1.530 (5)
C2A—C22A	1.520 (6)	C2B—C3B	1.538 (5)
C3A—C4A	1.501 (5)	C3B—C4B	1.520 (5)
C4A—C5A	1.513 (5)	C4B—C5B	1.510 (5)
C5A—C6A	1.533 (6)	C5B—C6B	1.521 (6)
C6A—C61A	1.531 (6)	C6B—C62B	1.531 (6)
C6A—C62A	1.532 (6)	C6B—C61B	1.543 (6)
C7A—C11A	1.488 (5)	C7B—C11B	1.473 (5)
C11A—C12A	1.377 (5)	C3B—H31B	0.945 (4)
C11A—C16A	1.392 (6)	C3B—H32B	0.947 (4)
C12A—C13A	1.379 (5)	C4B—H4B	1.127 (4)
C13A—C14A	1.391 (5)	C5B—H51B	0.907 (4)
C14A—C15A	1.390 (5)	C5B—H52B	1.062 (5)
C15A—C16A	1.371 (6)	C7B—H7B	0.968 (4)
C41A—C42A	1.351 (6)	C11B—C16B	1.380 (5)
C41A—C46A	1.369 (5)	C11B—C12B	1.386 (5)
C42A—C43A	1.356 (7)	C12B—C13B	1.381 (5)
C43A—C44A	1.374 (8)	C13B—C14B	1.379 (5)
C44A—C45A	1.366 (8)	C14B—C15B	1.395 (6)
C45A—C46A	1.370 (6)	C15B—C16B	1.360 (6)
C3A—H31A	1.027 (4)	C41B—C46B	1.347 (6)
C3A—H32A	1.005 (4)	C41B—C42B	1.380 (7)
C4A—H4A	0.955 (4)	C42B—C43B	1.374 (7)
C5A—H51A	0.982 (5)	C43B—C44B	1.350 (7)
C5A—H52A	0.975 (5)	C44B—C45B	1.360 (7)
C7A—H7A	0.938 (4)	C45B—C46B	1.369 (6)
C12A—H12A	0.899 (5)	C12B—H12B	1.118 (4)
C13A—H13A	1.187 (4)	C13B—H13B	0.895 (4)
C15A—H15A	0.954 (5)	C15B—H15B	0.928 (5)
C16A—H16A	0.866 (4)	C16B—H16B	0.994 (4)
C21A—H21A	1.113 (5)	C21B—H21B	0.922 (5)
C21A—H22A	0.919 (6)	C21B—H22B	0.915 (5)
C21A—H23A	0.873 (5)	C21B—H23B	1.213 (5)
C22A—H24A	0.957 (5)	C22B—H24B	0.868 (5)
C22A—H25A	1.044 (5)	C22B—H25B	0.990 (5)
C22A—H26A	0.981 (5)	C22B—H26B	1.122 (5)
C42A—H42A	1.073 (5)	C42B—H42B	0.922 (5)
C43A—H43A	0.871 (6)	C43B—H43B	0.973 (6)
C44A—H44A	0.904 (5)	C44B—H44B	1.087 (5)
C45A—H45A	1.038 (5)	C45B—H45B	0.964 (5)
C46A—H46A	0.849 (4)	C46B—H46B	0.849 (5)
C61A—H61A	1.109 (5)	C61B—H61B	1.089 (5)
C61A—H62A	1.005 (5)	C61B—H62B	1.044 (5)
C61A—H63A	0.921 (5)	C61B—H63B	0.953 (5)
C62A—H64A	0.938 (5)	C62B—H64B	0.915 (5)
C62A—H65A	0.955 (5)	C62B—H65B	1.053 (5)
C62A—H66A	1.087 (5)	C62B—H66B	0.932 (6)

O1A···O1B	7.998 (5)	O1A···H25Aⁱ	2.67
O1A···O1Aⁱ	5.993 (2)	O1B···H62Bⁱ	2.83
O1B···O1Bⁱ	5.993 (2)	O1A···H46Bⁱⁱⁱ	2.45
O1A···O1Bⁱⁱ	8.033 (5)	O1B···H46A^iv	2.74
O1A···C22Aⁱ	3.695 (6)	O2A···C45Aⁱ	3.344 (6)
O1B···C61Bⁱ	3.862 (6)	O2B···C45Bⁱ	3.307 (6)
O1A···C46Bⁱⁱⁱ	3.189 (5)	O2B···C44Bⁱ	3.325 (6)
O1B···C46A^iv	3.361 (5)

C14A—O2A—C41A	119.3 (3)	H65A—C62A—H66A	99.2 (4)
O1A—N1A—C2A	117.9 (3)	C14B—O2B—C41B	121.3 (3)
O1A—N1A—C6A	115.4 (3)	O1B—N1B—C6B	116.6 (3)
C2A—N1A—C6A	123.7 (3)	O1B—N1B—C2B	117.1 (3)
C7A—N2A—C4A	120.2 (3)	C6B—N1B—C2B	121.8 (3)
N1A—C2A—C3A	108.9 (3)	C7B—N2B—C4B	120.2 (3)
N1A—C2A—C22A	109.3 (3)	N1B—C2B—C22B	110.3 (3)
N1A—C2A—C21A	108.3 (3)	N1B—C2B—C21B	106.8 (3)
C21A—C2A—C3A	109.5 (3)	C22B—C2B—C21B	109.2 (4)
C22A—C2A—C3A	111.4 (3)	N1B—C2B—C3B	108.5 (3)
C22A—C2A—C21A	109.4 (4)	C22B—C2B—C3B	112.8 (3)
C4A—C3A—C2A	115.1 (3)	C21B—C2B—C3B	109.1 (3)
N2A—C4A—C3A	108.0 (3)	C4B—C3B—C2B	114.6 (3)
N2A—C4A—C5A	106.7 (3)	N2B—C4B—C5B	107.6 (3)
C3A—C4A—C5A	110.6 (3)	N2B—C4B—C3B	106.8 (3)
C4A—C5A—C6A	115.6 (3)	C5B—C4B—C3B	109.7 (3)
N1A—C6A—C5A	108.3 (3)	C4B—C5B—C6B	114.7 (3)
N1A—C6A—C61A	109.2 (3)	N1B—C6B—C5B	110.1 (3)
N1A—C6A—C62A	107.4 (3)	N1B—C6B—C62B	106.6 (3)
C61A—C6A—C5A	111.9 (3)	C5B—C6B—C62B	108.2 (4)
C62A—C6A—C5A	109.7 (4)	N1B—C6B—C61B	109.7 (4)
C61A—C6A—C62A	110.2 (3)	C5B—C6B—C61B	111.8 (3)
N2A—C7A—C11A	122.2 (4)	C62B—C6B—C61B	110.3 (3)
C12A—C11A—C7A	121.5 (4)	N2B—C7B—C11B	122.6 (3)
C16A—C11A—C7A	120.5 (3)	C16B—C11B—C12B	118.5 (4)
C12A—C11A—C16A	118.0 (4)	C16B—C11B—C7B	120.9 (3)
C11A—C12A—C13A	122.0 (4)	C12B—C11B—C7B	120.5 (4)
C12A—C13A—C14A	119.1 (4)	C13B—C12B—C11B	120.5 (4)
O2A—C14A—C13A	124.8 (4)	C14B—C13B—C12B	120.4 (4)
O2A—C14A—C15A	115.4 (4)	O2B—C14B—C13B	125.1 (4)
C15A—C14A—C13A	119.7 (4)	O2B—C14B—C15B	115.8 (4)
C16A—C15A—C14A	119.8 (4)	C13B—C14B—C15B	119.0 (4)
C15A—C16A—C11A	121.3 (4)	C16B—C15B—C14B	120.0 (4)
C42A—C41A—O2A	121.0 (4)	C15B—C16B—C11B	121.5 (4)
C46A—C41A—O2A	117.3 (4)	C46B—C41B—C42B	120.4 (4)
C42A—C41A—C46A	121.6 (4)	C46B—C41B—O2B	117.9 (5)
C41A—C42A—C43A	119.3 (5)	C42B—C41B—O2B	121.7 (4)
C42A—C43A—C44A	120.6 (5)	C43B—C42B—C41B	119.0 (5)
C45A—C44A—C43A	119.3 (5)	C44B—C43B—C42B	120.9 (5)
C44A—C45A—C46A	120.5 (5)	C43B—C44B—C45B	119.2 (5)
C41A—C46A—C45A	118.6 (4)	C44B—C45B—C46B	121.2 (5)
C2A—C3A—H31A	108.8 (4)	C41B—C46B—C45B	119.4 (5)
C2A—C3A—H32A	107.7 (4)	C4B—C3B—H31B	107.2 (4)
C4A—C3A—H31A	116.2 (4)	C2B—C3B—H31B	115.4 (4)
C4A—C3A—H32A	105.6 (4)	C4B—C3B—H32B	105.7 (4)
H31A—C3A—H32A	102.2 (3)	C2B—C3B—H32B	110.3 (4)
N2A—C4A—H4A	109.6 (3)	H31B—C3B—H32B	102.5 (3)
C3A—C4A—H4A	112.3 (4)	N2B—C4B—H4B	114.7 (3)
C5A—C4A—H4A	109.4 (4)	C5B—C4B—H4B	113.0 (3)
C4A—C5A—H51A	108.2 (4)	C3B—C4B—H4B	104.8 (3)
C4A—C5A—H52A	114.2 (4)	C4B—C5B—H51B	107.4 (4)
C6A—C5A—H51A	110.6 (4)	C6B—C5B—H51B	109.2 (4)
C6A—C5A—H52A	110.6 (4)	C4B—C5B—H52B	111.6 (4)
H51A—C5A—H52A	95.8 (4)	C6B—C5B—H52B	110.9 (4)
N2A—C7A—H7A	119.5 (4)	H51B—C5B—H52B	102.2 (4)
C11A—C7A—H7A	118.2 (4)	N2B—C7B—H7B	121.9 (4)
C11A—C12A—H12A	117.3 (4)	C11B—C7B—H7B	115.3 (4)
C13A—C12A—H12A	120.7 (4)	C13B—C12B—H12B	118.9 (4)
C12A—C13A—H13A	119.3 (4)	C11B—C12B—H12B	120.5 (4)
C14A—C13A—H13A	121.5 (4)	C14B—C13B—H13B	116.8 (4)
C14A—C15A—H15A	115.6 (4)	C12B—C13B—H13B	122.5 (5)
C16A—C15A—H15A	124.6 (4)	C16B—C15B—H15B	122.3 (5)
C11A—C16A—H16A	121.2 (5)	C14B—C15B—H15B	117.6 (4)
C15A—C16A—H16A	117.4 (5)	C15B—C16B—H16B	120.0 (5)
C2A—C21A—H21A	112.4 (4)	C11B—C16B—H16B	117.7 (4)
C2A—C21A—H22A	106.5 (4)	C2B—C21B—H21B	117.4 (4)
C2A—C21A—H23A	111.3 (4)	C2B—C21B—H22B	116.0 (5)
H21A—C21A—H22A	101.2 (4)	H21B—C21B—H22B	102.2 (4)
H21A—C21A—H23A	110.4 (5)	C2B—C21B—H23B	106.8 (4)
H22A—C21A—H23A	114.7 (5)	H21B—C21B—H23B	114.8 (5)
C2A—C22A—H24A	106.3 (4)	H22B—C21B—H23B	98.2 (4)
C2A—C22A—H25A	118.3 (4)	C2B—C22B—H25B	112.2 (4)
C2A—C22A—H26A	108.6 (4)	C2B—C22B—H26B	115.2 (4)
H24A—C22A—H25A	103.7 (4)	H25B—C22B—H26B	98.0 (4)
H24A—C22A—H26A	117.5 (5)	C43B—C42B—H42B	127.9 (6)
H25A—C22A—H26A	103.0 (4)	C41B—C42B—H42B	113.0 (6)
C41A—C42A—H42A	113.5 (5)	C44B—C43B—H43B	129.1 (6)
C43A—C42A—H42A	127.1 (5)	C42B—C43B—H43B	110.0 (6)
C42A—C43A—H43A	115.1 (7)	C43B—C44B—H44B	117.7 (6)
C44A—C43A—H43A	124.1 (7)	C45B—C44B—H44B	122.8 (6)
C43A—C44A—H44A	120.3 (7)	C44B—C45B—H45B	115.0 (6)
C45A—C44A—H44A	120.4 (7)	C46B—C45B—H45B	123.7 (6)
C44A—C45A—H45A	120.6 (5)	C41B—C46B—H46B	119.4 (5)
C46A—C45A—H45A	118.9 (6)	C45B—C46B—H46B	121.2 (6)
C41A—C46A—H46A	113.9 (5)	C6B—C61B—H61B	113.7 (4)
C45A—C46A—H46A	127.4 (5)	C6B—C61B—H62B	113.8 (4)
C6A—C61A—H61A	115.4 (4)	H61B—C61B—H62B	104.9 (5)
C6A—C61A—H62A	114.6 (4)	C6B—C61B—H63B	108.2 (4)
C6A—C61A—H63A	112.5 (4)	H61B—C61B—H63B	112.4 (4)
H61A—C61A—H62A	94.7 (4)	H62B—C61B—H63B	103.4 (4)
H61A—C61A—H63A	103.6 (4)	C6B—C62B—H64B	112.6 (4)
H62A—C61A—H63A	114.4 (5)	C6B—C62B—H65B	108.9 (4)
C6A—C62A—H64A	110.0 (4)	H64B—C62B—H65B	127.0 (6)
C6A—C62A—H65A	107.0 (4)	C6B—C62B—H66B	108.3 (5)
C6A—C62A—H66A	114.2 (4)	H64B—C62B—H66B	99.1 (5)
H64A—C62A—H65A	111.6 (6)	H65B—C62B—H66B	97.8 (4)
H64A—C62A—H66A	114.2 (4)

O1A—N1A—C2A—C3A	−158.2 (3)	O1B—N1B—C2B—C3B	−161.7 (3)
O1A—N1A—C6A—C5A	158.7 (3)	O1B—N1B—C6B—C5B	162.0 (3)
C6A—N1A—C2A—C3A	42.2 (5)	C6B—N1B—C2B—C3B	43.1 (5)
C2A—N1A—C6A—C5A	−41.3 (5)	C2B—N1B—C6B—C5B	−42.6 (5)
N1A—C2A—C3A—C4A	−46.9 (5)	N1B—C2B—C3B—C4B	−48.6 (4)
C4A—C5A—C6A—N1A	44.9 (5)	C4B—C5B—C6B—N1B	47.0 (5)
C2A—C3A—C4A—C5A	54.7 (5)	C2B—C3B—C4B—C5B	56.5 (4)
C3A—C4A—C5A—C6A	−54.0 (5)	C3B—C4B—C5B—C6B	−55.3 (4)
C2A—C3A—C4A—N2A	171.1 (3)	C2B—C3B—C4B—N2B	172.8 (3)
N2A—C4A—C5A—C6A	−171.2 (3)	N2B—C4B—C5B—C6B	−171.1 (3)
C7A—N2A—C4A—C3A	107.0 (5)	C7B—N2B—C4B—C3B	114.0 (4)
C7A—N2A—C4A—C5A	−134.1 (4)	C7B—N2B—C4B—C5B	−128.3 (4)
O1A—N1A—C2A—C22A	79.9 (4)	O1B—N1B—C2B—C22B	74.4 (4)
C6A—N1A—C2A—C22A	−79.7 (4)	C6B—N1B—C2B—C22B	−80.9 (5)
O1A—N1A—C2A—C21A	−39.2 (5)	O1B—N1B—C2B—C21B	−44.1 (5)
C6A—N1A—C2A—C21A	161.2 (4)	C6B—N1B—C2B—C21B	160.6 (4)
C22A—C2A—C3A—C4A	73.8 (4)	C22B—C2B—C3B—C4B	73.8 (4)
C21A—C2A—C3A—C4A	−165.1 (3)	C21B—C2B—C3B—C4B	−164.7 (3)
O1A—N1A—C6A—C61A	−79.2 (4)	O1B—N1B—C6B—C62B	44.9 (5)
C2A—N1A—C6A—C61A	80.8 (4)	C2B—N1B—C6B—C62B	−159.7 (4)
O1A—N1A—C6A—C62A	40.3 (5)	O1B—N1B—C6B—C61B	−74.5 (4)
C2A—N1A—C6A—C62A	−159.6 (4)	C2B—N1B—C6B—C61B	80.9 (4)
C4A—C5A—C6A—C61A	−75.5 (4)	C4B—C5B—C6B—C62B	163.1 (4)
C4A—C5A—C6A—C62A	161.9 (3)	C4B—C5B—C6B—C61B	−75.3 (4)
C4A—N2A—C7A—C11A	−178.6 (4)	C4B—N2B—C7B—C11B	−178.7 (3)
N2A—C7A—C11A—C12A	172.1 (4)	N2B—C7B—C11B—C16B	−11.5 (6)
N2A—C7A—C11A—C16A	−10.7 (7)	N2B—C7B—C11B—C12B	166.1 (4)
C16A—C11A—C12A—C13A	3.0 (6)	C16B—C11B—C12B—C13B	1.9 (6)
C7A—C11A—C12A—C13A	−179.7 (4)	C7B—C11B—C12B—C13B	−175.8 (4)
C11A—C12A—C13A—C14A	−1.2 (6)	C11B—C12B—C13B—C14B	0.1 (6)
C41A—O2A—C14A—C15A	168.0 (4)	C41B—O2B—C14B—C13B	−9.4 (7)
C41A—O2A—C14A—C13A	−15.2 (6)	C41B—O2B—C14B—C15B	175.2 (4)
C12A—C13A—C14A—O2A	−177.2 (4)	C12B—C13B—C14B—O2B	−177.9 (4)
C12A—C13A—C14A—C15A	−0.6 (6)	C12B—C13B—C14B—C15B	−2.6 (6)
O2A—C14A—C15A—C16A	177.4 (4)	O2B—C14B—C15B—C16B	178.9 (4)
C13A—C14A—C15A—C16A	0.4 (7)	C13B—C14B—C15B—C16B	3.2 (7)
C14A—C15A—C16A—C11A	1.5 (8)	C14B—C15B—C16B—C11B	−1.2 (7)
C12A—C11A—C16A—C15A	−3.2 (7)	C12B—C11B—C16B—C15B	−1.3 (6)
C7A—C11A—C16A—C15A	179.5 (4)	C7B—C11B—C16B—C15B	176.3 (4)
C14A—O2A—C41A—C42A	−61.6 (5)	C14B—O2B—C41B—C46B	119.3 (5)
C14A—O2A—C41A—C46A	120.9 (4)	C14B—O2B—C41B—C42B	−63.9 (6)
C46A—C41A—C42A—C43A	0.1 (7)	C46B—C41B—C42B—C43B	−0.6 (8)
O2A—C41A—C42A—C43A	−177.3 (4)	O2B—C41B—C42B—C43B	−177.3 (4)
C41A—C42A—C43A—C44A	−1.3 (8)	C41B—C42B—C43B—C44B	0.0 (8)
C42A—C43A—C44A—C45A	3.3 (9)	C42B—C43B—C44B—C45B	0.7 (8)
C43A—C44A—C45A—C46A	−3.9 (8)	C43B—C44B—C45B—C46B	−0.9 (8)
C42A—C41A—C46A—C45A	−0.7 (7)	C42B—C41B—C46B—C45B	0.4 (7)
O2A—C41A—C46A—C45A	176.8 (4)	O2B—C41B—C46B—C45B	177.2 (4)
C44A—C45A—C46A—C41A	2.6 (7)	C44B—C45B—C46B—C41B	0.3 (7)

Symmetry codes: (i) x, y+1, z; (ii) x+1/2, −y+3, z; (iii) −x+1/2, y+1, z+1/2; (iv) −x+1/2, y+2, z+1/2.

(14) 4-(4-mesylphenylmethyleneamino)-2,2,6,6-tetramethylpiperidin-1-oxyl top

Crystal data top

C₁₇H₂₅N₂O₃S	F(000) = 724.00
M_r = 337.46	D_x = 1.230 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
a = 11.1835 (18) Å	Cell parameters from 24 reflections
b = 15.487 (2) Å	θ = 17.2–17.4°
c = 11.5660 (18) Å	µ = 0.19 mm⁻¹
β = 114.539 (11)°	T = 294 K
V = 1822.2 (5) Å³	Prism, orange
Z = 4	0.40 × 0.40 × 0.25 mm

Data collection top

Rigaku AFC7R diffractometer	3223 reflections with I > 2σ(I)
Radiation source: Rigaku rotating anode	R_int = 0.011
Graphite monochromator	θ_max = 27.5°, θ_min = 2.0°
ω–2θ scans	h = 0→14
Absorption correction: ψ scans(north,Phillips & Mathews,1968)	k = 0→20
T_min = 0.976, T_max = 1.000	l = −15→13
4390 measured reflections	3 standard reflections every 150 reflections
4184 independent reflections	intensity decay: 2.1%

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.041	Hydrogen site location: difmap and geom
wR(F²) = 0.124	All H-atom parameters refined
S = 1.01	Calculated w = 1/[σ²(F_o²) + (0.0591P)² + 0.4517P] where P = (F_o² + 2F_c²)/3
4184 reflections	(Δ/σ)_max = 0.002
308 parameters	Δρ_max = 0.22 e Å⁻³
0 restraints	Δρ_min = −0.37 e Å⁻³

Special details top

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
S1	0.67906 (4)	0.23050 (3)	0.32526 (4)	0.04993 (14)
O1	−0.32575 (13)	−0.17790 (10)	0.14263 (17)	0.0777 (5)
O2	0.79800 (13)	0.19177 (11)	0.41330 (16)	0.0791 (5)
O3	0.66697 (16)	0.24230 (11)	0.19877 (14)	0.0780 (5)
N1	−0.21831 (13)	−0.13885 (9)	0.16040 (14)	0.0466 (3)
N2	0.13684 (14)	−0.01037 (10)	0.22219 (15)	0.0550 (4)
C2	−0.20524 (16)	−0.04898 (11)	0.21003 (16)	0.0455 (4)
C3	−0.08984 (17)	−0.00427 (11)	0.1966 (2)	0.0494 (4)
C4	0.03315 (16)	−0.05922 (11)	0.24018 (18)	0.0477 (4)
C5	0.00093 (18)	−0.13977 (12)	0.1584 (2)	0.0502 (4)
C6	−0.10558 (15)	−0.19526 (10)	0.17114 (15)	0.0437 (3)
C7	0.23087 (16)	0.01568 (11)	0.32082 (18)	0.0480 (4)
C11	0.34033 (15)	0.06780 (10)	0.31885 (16)	0.0437 (3)
C12	0.34551 (16)	0.09204 (12)	0.20499 (17)	0.0493 (4)
C13	0.44757 (16)	0.14254 (12)	0.20545 (17)	0.0480 (4)
C14	0.54568 (14)	0.16726 (10)	0.32084 (15)	0.0426 (3)
C15	0.54249 (17)	0.14415 (12)	0.43496 (17)	0.0498 (4)
C16	0.43876 (17)	0.09491 (12)	0.43305 (17)	0.0498 (4)
C17	0.6596 (4)	0.32873 (17)	0.3911 (4)	0.0928 (10)
C21	−0.1871 (3)	−0.05072 (16)	0.3485 (2)	0.0635 (5)
C22	−0.3321 (2)	−0.00156 (16)	0.1293 (3)	0.0666 (5)
C61	−0.0540 (2)	−0.24426 (14)	0.2979 (2)	0.0611 (5)
C62	−0.1565 (2)	−0.26078 (14)	0.0635 (2)	0.0607 (5)
H4	0.0623 (18)	−0.0726 (12)	0.3295 (18)	0.046 (5)*
H7	0.232 (2)	0.0055 (14)	0.401 (2)	0.067 (6)*
H12	0.274 (2)	0.0727 (13)	0.1256 (19)	0.058 (5)*
H13	0.449 (2)	0.1593 (14)	0.129 (2)	0.064 (6)*
H15	0.613 (2)	0.1604 (14)	0.5149 (19)	0.064 (6)*
H16	0.4339 (19)	0.0787 (12)	0.5097 (19)	0.055 (5)*
H21	−0.251 (2)	−0.0867 (16)	0.358 (2)	0.085 (8)*
H22	−0.102 (2)	−0.0751 (15)	0.408 (2)	0.070 (7)*
H23	−0.195 (2)	0.0086 (17)	0.374 (2)	0.083 (7)*
H24	−0.324 (2)	0.0591 (17)	0.148 (2)	0.073 (7)*
H25	−0.352 (2)	−0.0051 (15)	0.039 (2)	0.073 (7)*
H26	−0.405 (3)	−0.0240 (17)	0.143 (2)	0.089 (8)*
H31	−0.1127 (19)	0.0106 (13)	0.110 (2)	0.058 (5)*
H32	−0.072 (2)	0.0470 (16)	0.241 (2)	0.069 (6)*
H51	−0.0254 (19)	−0.1239 (13)	0.069 (2)	0.060 (6)*
H52	0.075 (2)	−0.1731 (14)	0.1822 (19)	0.062 (6)*
H61	−0.123 (3)	−0.2753 (16)	0.308 (2)	0.083 (7)*
H62	0.015 (3)	−0.2881 (19)	0.304 (2)	0.101 (9)*
H63	−0.018 (2)	−0.2040 (15)	0.371 (2)	0.066 (6)*
H64	−0.224 (3)	−0.2983 (16)	0.071 (2)	0.087 (7)*
H65	−0.192 (2)	−0.2337 (15)	−0.018 (2)	0.076 (7)*
H66	−0.079 (3)	−0.2951 (17)	0.067 (2)	0.089 (8)*
H71	0.723 (3)	0.372 (2)	0.384 (3)	0.113 (9)*
H72	0.583 (3)	0.350 (2)	0.314 (3)	0.104 (11)*
H73	0.665 (4)	0.318 (3)	0.474 (5)	0.21 (2)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0416 (2)	0.0528 (3)	0.0593 (3)	−0.01223 (17)	0.02488 (19)	−0.00821 (19)
O1	0.0495 (7)	0.0680 (9)	0.1266 (13)	−0.0205 (6)	0.0476 (8)	−0.0190 (9)
O2	0.0384 (7)	0.0967 (12)	0.0918 (11)	−0.0102 (7)	0.0168 (7)	0.0035 (9)
O3	0.0763 (10)	0.1010 (12)	0.0639 (9)	−0.0328 (9)	0.0363 (8)	−0.0025 (8)
N1	0.0373 (7)	0.0457 (7)	0.0611 (8)	−0.0070 (5)	0.0248 (6)	−0.0067 (6)
N2	0.0429 (7)	0.0615 (9)	0.0631 (9)	−0.0147 (7)	0.0244 (7)	−0.0016 (7)
C2	0.0440 (8)	0.0423 (8)	0.0568 (9)	0.0010 (7)	0.0272 (7)	−0.0022 (7)
C3	0.0500 (9)	0.0393 (8)	0.0639 (11)	−0.0053 (7)	0.0287 (8)	−0.0020 (8)
C4	0.0386 (8)	0.0520 (9)	0.0550 (10)	−0.0093 (7)	0.0218 (7)	0.0009 (7)
C5	0.0435 (9)	0.0501 (9)	0.0667 (11)	−0.0008 (7)	0.0327 (8)	−0.0037 (8)
C6	0.0456 (8)	0.0391 (8)	0.0524 (9)	−0.0013 (6)	0.0264 (7)	−0.0039 (7)
C7	0.0424 (8)	0.0468 (9)	0.0589 (10)	−0.0045 (7)	0.0252 (8)	−0.0020 (8)
C11	0.0357 (7)	0.0419 (8)	0.0547 (9)	−0.0017 (6)	0.0201 (7)	−0.0019 (7)
C12	0.0369 (8)	0.0586 (10)	0.0491 (9)	−0.0084 (7)	0.0147 (7)	−0.0074 (8)
C13	0.0411 (8)	0.0580 (10)	0.0465 (9)	−0.0055 (7)	0.0196 (7)	−0.0017 (7)
C14	0.0340 (7)	0.0432 (8)	0.0508 (8)	−0.0031 (6)	0.0178 (6)	−0.0024 (7)
C15	0.0431 (8)	0.0547 (10)	0.0461 (9)	−0.0087 (7)	0.0133 (7)	−0.0039 (7)
C16	0.0480 (9)	0.0552 (10)	0.0475 (9)	−0.0063 (7)	0.0209 (7)	0.0007 (7)
C17	0.104 (2)	0.0543 (13)	0.147 (3)	−0.0241 (14)	0.080 (2)	−0.0284 (16)
C21	0.0780 (14)	0.0610 (12)	0.0667 (12)	−0.0021 (11)	0.0450 (12)	−0.0067 (10)
C22	0.0516 (11)	0.0633 (13)	0.0892 (17)	0.0138 (9)	0.0338 (11)	0.0063 (11)
C61	0.0725 (13)	0.0525 (11)	0.0602 (12)	−0.0003 (10)	0.0295 (10)	0.0054 (9)
C62	0.0748 (13)	0.0521 (11)	0.0642 (12)	−0.0108 (10)	0.0379 (11)	−0.0138 (9)

Geometric parameters (Å, º) top

S1—O3	1.4240 (16)	C11—C12	1.393 (2)
S1—O2	1.4285 (16)	C12—C13	1.382 (2)
S1—C17	1.755 (3)	C12—H12	0.98 (2)
S1—C14	1.7674 (16)	C13—C14	1.384 (2)
O1—N1	1.2832 (17)	C13—H13	0.93 (2)
N1—C2	1.489 (2)	C14—C15	1.382 (2)
N1—C6	1.496 (2)	C15—C16	1.381 (2)
N2—C4	1.470 (2)	C15—H15	0.97 (2)
N2—C7	1.254 (2)	C16—H16	0.94 (2)
C2—C22	1.525 (3)	C17—H71	1.01 (3)
C2—C3	1.528 (2)	C17—H72	1.00 (3)
C2—C21	1.529 (3)	C17—H73	0.96 (5)
C3—C4	1.515 (2)	C21—H21	0.95 (3)
C3—H31	0.95 (2)	C21—H22	0.99 (2)
C3—H32	0.92 (2)	C21—H23	0.98 (3)
C4—C5	1.516 (3)	C22—H24	0.96 (2)
C4—H4	0.968 (19)	C22—H25	0.97 (2)
C5—C6	1.525 (2)	C22—H26	0.96 (3)
C5—H51	0.98 (2)	C61—H61	0.96 (3)
C5—H52	0.91 (2)	C61—H62	1.01 (3)
C6—C62	1.522 (2)	C61—H63	0.99 (2)
C6—C61	1.535 (3)	C62—H64	0.99 (3)
C7—C11	1.474 (2)	C62—H65	0.95 (2)
C7—H7	0.93 (2)	C62—H66	1.00 (3)
C11—C16	1.387 (2)

O3—S1—O2	116.69 (10)	C13—C12—C11	120.49 (15)
O3—S1—C17	111.00 (17)	C13—C12—H12	121.9 (12)
O2—S1—C17	107.55 (17)	C11—C12—H12	117.6 (12)
O3—S1—C14	108.81 (8)	C12—C13—C14	118.88 (16)
O2—S1—C14	108.23 (9)	C12—C13—H13	119.8 (13)
C17—S1—C14	103.75 (11)	C14—C13—H13	121.4 (13)
O1—N1—C2	115.95 (13)	C15—C14—C13	121.65 (15)
O1—N1—C6	116.04 (13)	C15—C14—S1	118.17 (12)
C2—N1—C6	124.70 (12)	C13—C14—S1	120.18 (13)
C7—N2—C4	116.71 (16)	C16—C15—C14	118.84 (15)
N1—C2—C22	107.25 (15)	C16—C15—H15	120.5 (12)
N1—C2—C3	109.64 (13)	C14—C15—H15	120.6 (12)
C22—C2—C3	109.26 (16)	C15—C16—C11	120.76 (16)
N1—C2—C21	109.65 (15)	C15—C16—H16	120.5 (12)
C22—C2—C21	109.61 (17)	C11—C16—H16	118.7 (12)
C3—C2—C21	111.35 (16)	S1—C17—H71	109.1 (17)
C4—C3—C2	113.58 (14)	S1—C17—H72	96.7 (18)
C4—C3—H31	107.2 (12)	H71—C17—H72	94 (2)
C2—C3—H31	110.3 (12)	S1—C17—H73	109 (3)
C4—C3—H32	110.3 (14)	H71—C17—H73	117 (3)
C2—C3—H32	108.8 (13)	H72—C17—H73	129 (3)
H31—C3—H32	106.4 (18)	C2—C21—H21	111.0 (15)
N2—C4—C3	108.94 (14)	C2—C21—H22	113.9 (13)
N2—C4—C5	109.40 (14)	H21—C21—H22	104 (2)
C3—C4—C5	107.88 (14)	C2—C21—H23	107.9 (14)
N2—C4—H4	109.0 (11)	H21—C21—H23	111 (2)
C3—C4—H4	109.4 (11)	H22—C21—H23	109.4 (19)
C5—C4—H4	112.1 (11)	C2—C22—H24	110.9 (14)
C4—C5—C6	113.34 (14)	C2—C22—H25	111.8 (13)
C4—C5—H51	109.9 (12)	H24—C22—H25	105 (2)
C6—C5—H51	109.8 (12)	C2—C22—H26	111.5 (15)
C4—C5—H52	109.1 (13)	H24—C22—H26	109 (2)
C6—C5—H52	107.1 (13)	H25—C22—H26	109 (2)
H51—C5—H52	107.4 (17)	C6—C61—H61	111.5 (15)
N1—C6—C62	107.78 (15)	C6—C61—H62	111.9 (15)
N1—C6—C5	109.15 (13)	H61—C61—H62	107 (2)
C62—C6—C5	109.79 (15)	C6—C61—H63	111.1 (12)
N1—C6—C61	109.72 (14)	H61—C61—H63	106.1 (19)
C62—C6—C61	108.45 (16)	H62—C61—H63	109 (2)
C5—C6—C61	111.86 (16)	C6—C62—H64	111.0 (15)
N2—C7—C11	123.36 (17)	C6—C62—H65	112.0 (14)
N2—C7—H7	120.5 (13)	H64—C62—H65	109 (2)
C11—C7—H7	116.0 (13)	C6—C62—H66	107.3 (14)
C16—C11—C12	119.36 (15)	H64—C62—H66	111 (2)
C16—C11—C7	119.11 (16)	H65—C62—H66	106 (2)
C12—C11—C7	121.52 (15)

O1—N1—C2—C3	−166.73 (16)	C4—C5—C6—C62	165.52 (17)
O1—N1—C6—C5	165.91 (16)	C4—C5—C6—C61	−74.0 (2)
C6—N1—C2—C3	34.7 (2)	C4—N2—C7—C11	−178.00 (15)
C2—N1—C6—C5	−35.6 (2)	N2—C7—C11—C16	178.84 (18)
N1—C2—C3—C4	−45.9 (2)	N2—C7—C11—C12	0.3 (3)
C4—C5—C6—N1	47.6 (2)	C16—C11—C12—C13	0.0 (3)
C2—C3—C4—C5	60.9 (2)	C7—C11—C12—C13	178.53 (16)
C3—C4—C5—C6	−62.0 (2)	C11—C12—C13—C14	1.2 (3)
C2—C3—C4—N2	179.57 (15)	C12—C13—C14—C15	−1.3 (3)
N2—C4—C5—C6	179.67 (15)	C12—C13—C14—S1	179.06 (13)
C7—N2—C4—C3	109.25 (19)	O3—S1—C14—C15	176.55 (14)
C7—N2—C4—C5	−133.05 (18)	O2—S1—C14—C15	48.83 (17)
O1—N1—C2—C22	−48.2 (2)	C17—S1—C14—C15	−65.2 (2)
C6—N1—C2—C22	153.25 (16)	O3—S1—C14—C13	−3.83 (18)
O1—N1—C2—C21	70.7 (2)	O2—S1—C14—C13	−131.55 (15)
C6—N1—C2—C21	−87.80 (19)	C17—S1—C14—C13	114.4 (2)
C22—C2—C3—C4	−163.14 (17)	C13—C14—C15—C16	0.2 (3)
C21—C2—C3—C4	75.6 (2)	S1—C14—C15—C16	179.86 (14)
O1—N1—C6—C62	46.7 (2)	C14—C15—C16—C11	1.0 (3)
C2—N1—C6—C62	−154.76 (16)	C12—C11—C16—C15	−1.2 (3)
O1—N1—C6—C61	−71.2 (2)	C7—C11—C16—C15	−179.69 (16)
C2—N1—C6—C61	87.33 (19)

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Format		BIBTeX
		EndNote
		RefMan
		Refer
		Medline
		CIF
		SGML
		Text
		Plain Text