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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.

Supporting information

cif

Crystallographic Information File (CIF)
Contains datablocks 8a, 8b, 9, 10, 11a, 11b, 12, 13, 14, text

hkl

Structure factor file (CIF format)
Contains datablock 8a

hkl

Structure factor file (CIF format)
Contains datablock 8b

hkl

Structure factor file (CIF format)
Contains datablock 9

hkl

Structure factor file (CIF format)
Contains datablock 10

hkl

Structure factor file (CIF format)
Contains datablock 11a

hkl

Structure factor file (CIF format)
Contains datablock 11b

hkl

Structure factor file (CIF format)
Contains datablock 12

hkl

Structure factor file (CIF format)
Contains datablock 13

hkl

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
C16H23N2ODx = 1.127 Mg m3
Mr = 259.37Melting point: not measured K
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
a = 12.684 (7) ÅCell parameters from 25 reflections
b = 11.740 (2) Åθ = 14.8–17.4°
c = 11.024 (3) ŵ = 0.07 mm1
β = 111.40 (4)°T = 296 K
V = 1528.3 (9) Å3Prism, orange
Z = 40.50 × 0.40 × 0.20 mm
F(000) = 564.00
Data collection top
Rigaku AFC7R
diffractometer
Rint = 0.016
Radiation source: Rigaku rotating anodeθmax = 27.5°, θmin = 2.6°
Graphite monochromatorh = 1615
ω–2θ scansk = 150
3712 measured reflectionsl = 014
3528 independent reflections3 standard reflections every 150 reflections
2110 reflections with I > 2σ(I) intensity decay: 7.2%
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: difmap and geom
R[F2 > 2σ(F2)] = 0.050All H-atom parameters refined
wR(F2) = 0.147Calculated w = 1/[σ2(Fo2) + (0.0684P)2 + 0.1077P]
where P = (Fo2 + 2Fc2)/3
S = 1.01(Δ/σ)max = 0.001
3528 reflectionsΔρmax = 0.17 e Å3
265 parametersΔρmin = 0.17 e Å3
0 restraintsExtinction correction: SHELXL-97 (Sheldrick, 1997), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction 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
xyzUiso*/Ueq
O10.45509 (13)0.79615 (11)0.29802 (15)0.0725 (4)
N10.40152 (12)0.71365 (12)0.22545 (13)0.0487 (4)
N20.22404 (13)0.43611 (13)0.00187 (13)0.0541 (4)
C20.47296 (14)0.62041 (15)0.20449 (16)0.0519 (5)
C30.39983 (15)0.54071 (17)0.09712 (17)0.0512 (5)
C40.28888 (15)0.50776 (14)0.10926 (17)0.0492 (4)
C50.22180 (15)0.61558 (16)0.10554 (18)0.0501 (4)
C60.28115 (15)0.70026 (15)0.21364 (16)0.0500 (4)
C70.21319 (15)0.33288 (15)0.02044 (18)0.0514 (4)
C110.14956 (13)0.25068 (15)0.08102 (17)0.0504 (4)
C120.10021 (16)0.28265 (18)0.21091 (18)0.0568 (5)
C130.03793 (17)0.2045 (2)0.3032 (2)0.0665 (6)
C140.02475 (18)0.0948 (2)0.2672 (2)0.0690 (6)
C150.07377 (18)0.06236 (18)0.1395 (3)0.0716 (6)
C160.13617 (17)0.13984 (17)0.0463 (2)0.0639 (5)
C210.5296 (2)0.5574 (2)0.3338 (2)0.0764 (7)
C220.5621 (2)0.6752 (3)0.1607 (3)0.0803 (8)
C610.2775 (2)0.6621 (2)0.3451 (2)0.0705 (6)
C620.2248 (2)0.8166 (2)0.1788 (3)0.0712 (6)
H40.3008 (14)0.4687 (15)0.1878 (18)0.049 (5)*
H70.2444 (16)0.2998 (16)0.109 (2)0.063 (5)*
H120.1109 (15)0.3629 (17)0.2339 (17)0.057 (5)*
H130.005 (2)0.231 (2)0.394 (3)0.094 (8)*
H140.0193 (19)0.038 (2)0.327 (2)0.085 (7)*
H150.069 (2)0.018 (2)0.109 (2)0.092 (7)*
H160.1742 (19)0.116 (2)0.040 (2)0.084 (7)*
H210.472 (2)0.518 (2)0.358 (2)0.089 (8)*
H220.582 (2)0.505 (2)0.330 (3)0.097 (8)*
H230.571 (2)0.612 (2)0.400 (3)0.098 (8)*
H240.527 (2)0.717 (2)0.080 (3)0.113 (10)*
H250.611 (2)0.614 (3)0.152 (3)0.112 (9)*
H260.607 (2)0.726 (2)0.229 (3)0.099 (8)*
H310.3813 (14)0.5826 (15)0.0117 (18)0.052 (5)*
H320.4418 (17)0.4737 (18)0.101 (2)0.068 (6)*
H510.1479 (15)0.5976 (16)0.1106 (16)0.053 (5)*
H520.2068 (15)0.6507 (16)0.0179 (19)0.058 (5)*
H610.3057 (17)0.5859 (19)0.3645 (19)0.064 (6)*
H620.200 (2)0.663 (2)0.344 (2)0.104 (9)*
H630.328 (2)0.712 (2)0.417 (2)0.091 (8)*
H640.145 (2)0.804 (2)0.166 (3)0.103 (9)*
H650.258 (2)0.872 (2)0.250 (2)0.089 (7)*
H660.238 (2)0.848 (2)0.099 (3)0.095 (8)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0789 (9)0.0533 (8)0.0814 (10)0.0198 (7)0.0246 (8)0.0270 (7)
N10.0560 (8)0.0411 (8)0.0464 (8)0.0066 (6)0.0157 (6)0.0083 (6)
N20.0654 (10)0.0455 (9)0.0412 (8)0.0070 (7)0.0072 (7)0.0058 (6)
C20.0479 (9)0.0555 (11)0.0454 (9)0.0023 (8)0.0090 (8)0.0108 (8)
C30.0534 (10)0.0489 (10)0.0437 (9)0.0076 (8)0.0088 (8)0.0091 (8)
C40.0619 (11)0.0404 (9)0.0359 (8)0.0057 (8)0.0067 (8)0.0022 (7)
C50.0469 (10)0.0541 (11)0.0478 (10)0.0044 (8)0.0154 (8)0.0042 (8)
C60.0555 (10)0.0479 (10)0.0498 (9)0.0037 (8)0.0231 (8)0.0075 (8)
C70.0522 (10)0.0450 (10)0.0468 (10)0.0012 (8)0.0059 (8)0.0023 (8)
C110.0444 (9)0.0452 (9)0.0535 (10)0.0037 (7)0.0083 (8)0.0093 (8)
C120.0559 (10)0.0545 (12)0.0544 (11)0.0047 (9)0.0133 (9)0.0097 (9)
C130.0575 (12)0.0792 (16)0.0540 (12)0.0071 (10)0.0100 (9)0.0193 (11)
C140.0573 (12)0.0640 (13)0.0788 (15)0.0083 (10)0.0167 (11)0.0324 (12)
C150.0667 (13)0.0461 (12)0.0907 (17)0.0018 (10)0.0154 (12)0.0152 (11)
C160.0631 (12)0.0464 (11)0.0674 (13)0.0025 (9)0.0062 (10)0.0046 (10)
C210.0735 (15)0.0752 (16)0.0553 (12)0.0171 (14)0.0066 (12)0.0110 (12)
C220.0553 (12)0.108 (2)0.0783 (17)0.0193 (14)0.0246 (12)0.0312 (16)
C610.0900 (17)0.0726 (16)0.0584 (13)0.0148 (14)0.0383 (12)0.0105 (12)
C620.0776 (16)0.0590 (13)0.0809 (16)0.0113 (11)0.0336 (13)0.0098 (12)
Geometric parameters (Å, º) top
O1—N11.2818 (18)C12—C131.384 (3)
N1—C21.492 (2)C12—H120.997 (19)
N1—C61.492 (2)C13—C141.376 (3)
N2—C41.466 (2)C13—H130.98 (3)
N2—C71.254 (2)C14—C151.369 (3)
C2—C221.525 (3)C14—H140.96 (2)
C2—C31.528 (2)C15—C161.384 (3)
C2—C211.533 (3)C15—H151.01 (3)
C3—C41.512 (3)C16—H160.94 (2)
C3—H311.011 (18)C21—H210.98 (3)
C3—H320.94 (2)C21—H220.92 (3)
C4—C51.517 (3)C21—H230.97 (3)
C4—H40.942 (18)C22—H240.97 (3)
C5—C61.523 (2)C22—H250.97 (3)
C5—H510.982 (18)C22—H260.97 (3)
C5—H521.003 (19)C61—H610.96 (2)
C6—C621.524 (3)C61—H620.98 (3)
C6—C611.533 (3)C61—H631.00 (3)
C7—C111.475 (2)C62—H640.98 (3)
C7—H70.99 (2)C62—H650.99 (2)
C11—C161.384 (3)C62—H661.02 (3)
C11—C121.389 (3)
O1···O1i5.6173 (16)O1···H32ii2.50 (2)
O1···O1ii6.1447 (13)O1···H22ii2.78 (3)
O1···C3ii3.378 (3)O1···H24i2.91 (3)
O1···C21ii3.429 (3)O1···H31i3.172 (18)
O1—N1—C2115.94 (14)C13—C12—C11120.0 (2)
O1—N1—C6115.24 (13)C13—C12—H12122.2 (11)
C2—N1—C6124.68 (13)C11—C12—H12117.7 (10)
C7—N2—C4117.31 (15)C14—C13—C12120.4 (2)
N1—C2—C22107.58 (18)C14—C13—H13122.4 (15)
N1—C2—C3109.75 (14)C12—C13—H13117.3 (15)
C22—C2—C3108.88 (17)C15—C14—C13120.0 (2)
N1—C2—C21108.39 (16)C15—C14—H14116.2 (14)
C22—C2—C21110.4 (2)C13—C14—H14123.8 (14)
C3—C2—C21111.77 (17)C14—C15—C16120.2 (2)
C4—C3—C2114.18 (15)C14—C15—H15122.7 (14)
C4—C3—H31107.4 (10)C16—C15—H15117.0 (14)
C2—C3—H31107.0 (10)C11—C16—C15120.5 (2)
C4—C3—H32108.2 (12)C11—C16—H16119.6 (15)
C2—C3—H32107.8 (12)C15—C16—H16119.8 (15)
H31—C3—H32112.3 (16)C2—C21—H21109.5 (14)
N2—C4—C3109.22 (14)C2—C21—H22112.3 (17)
N2—C4—C5108.54 (14)H21—C21—H22109 (2)
C3—C4—C5108.36 (15)C2—C21—H23108.5 (15)
N2—C4—H4110.0 (10)H21—C21—H23111 (2)
C3—C4—H4111.3 (10)H22—C21—H23107 (2)
C5—C4—H4109.3 (10)C2—C22—H24110.8 (17)
C4—C5—C6114.28 (15)C2—C22—H25106.7 (17)
C4—C5—H51110.9 (11)H24—C22—H25112 (2)
C6—C5—H51107.8 (10)C2—C22—H26107.6 (15)
C4—C5—H52106.1 (11)H24—C22—H26110 (2)
C6—C5—H52110.6 (11)H25—C22—H26109 (2)
H51—C5—H52107.0 (15)C6—C61—H61110.3 (12)
N1—C6—C5109.56 (14)C6—C61—H62111.1 (15)
N1—C6—C62107.37 (16)H61—C61—H62108 (2)
C5—C6—C62109.58 (17)C6—C61—H63110.3 (14)
N1—C6—C61109.31 (17)H61—C61—H63106.9 (18)
C5—C6—C61111.84 (17)H62—C61—H63110 (2)
C62—C6—C61109.09 (18)C6—C62—H64105.7 (15)
N2—C7—C11123.53 (17)C6—C62—H65111.7 (13)
N2—C7—H7122.7 (11)H64—C62—H65109 (2)
C11—C7—H7113.7 (11)C6—C62—H66109.4 (14)
C16—C11—C12118.97 (17)H64—C62—H66114 (2)
C16—C11—C7119.61 (17)H65—C62—H66106.8 (19)
C12—C11—C7121.41 (17)
O1—N1—C2—C2251.1 (2)C2—N1—C6—C534.9 (2)
C6—N1—C2—C22152.96 (17)C2—N1—C6—C62153.78 (16)
O1—N1—C2—C3169.38 (15)O1—N1—C6—C6168.1 (2)
C6—N1—C2—C334.6 (2)C2—N1—C6—C6188.02 (19)
O1—N1—C2—C2168.3 (2)C4—C5—C6—C62163.45 (17)
C6—N1—C2—C2187.7 (2)C4—C5—C6—C6175.5 (2)
N1—C2—C3—C445.5 (2)C4—N2—C7—C11179.41 (16)
C22—C2—C3—C4163.0 (2)N2—C7—C11—C16176.11 (19)
C21—C2—C3—C474.8 (2)N2—C7—C11—C122.4 (3)
C7—N2—C4—C3109.92 (19)C16—C11—C12—C130.6 (3)
C7—N2—C4—C5132.12 (18)C7—C11—C12—C13177.91 (17)
C4—C5—C6—N145.9 (2)C11—C12—C13—C140.2 (3)
C2—C3—C4—C559.2 (2)C12—C13—C14—C150.3 (3)
C3—C4—C5—C659.6 (2)C13—C14—C15—C160.3 (3)
C2—C3—C4—N2177.30 (15)C12—C11—C16—C150.5 (3)
N2—C4—C5—C6178.13 (15)C7—C11—C16—C15177.99 (19)
O1—N1—C6—C5169.01 (15)C14—C15—C16—C110.1 (3)
O1—N1—C6—C6250.1 (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
C16H23N2ODx = 1.165 Mg m3
Mr = 259.37Melting point: not measured K
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
a = 12.5774 (14) ÅCell parameters from 25 reflections
b = 11.6228 (16) Åθ = 12.9–15.2°
c = 10.8229 (17) ŵ = 0.07 mm1
β = 110.853 (9)°T = 100 K
V = 1478.5 (3) Å3Prism, orange
Z = 40.35 × 0.35 × 0.20 mm
F(000) = 564
Data collection top
Rigaku AFC7R
diffractometer
Rint = 0.023
Radiation source: Rigaku rotating anodeθmax = 27.5°, θmin = 2.5°
Graphite monochromatorh = 016
ω–2θ scansk = 1515
7062 measured reflectionsl = 1413
3383 independent reflections3 standard reflections every 150 reflections
2731 reflections with I > 2σ(I) intensity decay: 0.5%
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.036Hydrogen site location: difference Fourier map
wR(F2) = 0.099All H-atom parameters refined
S = 1.02Calculated w = 1/[σ2(Fo2) + (0.0459P)2 + 0.3544P]
where P = (Fo2 + 2Fc2)/3
3383 reflections(Δ/σ)max = 0.001
264 parametersΔρmax = 0.27 e Å3
0 restraintsΔρmin = 0.18 e Å3
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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
O10.45309 (7)0.80100 (7)0.29639 (8)0.0272 (2)
N10.39996 (8)0.71694 (8)0.22244 (9)0.0192 (2)
N20.22530 (8)0.43205 (8)0.00384 (9)0.0217 (2)
C20.47332 (9)0.62293 (9)0.20138 (10)0.0205 (2)
C30.40119 (9)0.54054 (10)0.09327 (10)0.0202 (2)
C40.28946 (9)0.50573 (9)0.10809 (10)0.0199 (2)
C50.22008 (9)0.61410 (9)0.10334 (11)0.0200 (2)
C60.27928 (9)0.70112 (9)0.21241 (10)0.0197 (2)
C70.21226 (9)0.32793 (9)0.02204 (10)0.0203 (2)
C110.14787 (9)0.24433 (9)0.08008 (10)0.0200 (2)
C120.09898 (9)0.27602 (10)0.21320 (11)0.0224 (2)
C130.03567 (10)0.19668 (10)0.30631 (11)0.0245 (2)
C140.02034 (9)0.08542 (10)0.26863 (12)0.0252 (2)
C150.06954 (10)0.05302 (10)0.13676 (12)0.0258 (2)
C160.13327 (9)0.13204 (10)0.04302 (12)0.0238 (2)
C210.53210 (11)0.56092 (11)0.33356 (12)0.0283 (3)
C220.56274 (10)0.67946 (12)0.15513 (13)0.0296 (3)
C610.27685 (11)0.66206 (11)0.34716 (11)0.0261 (2)
C620.22004 (11)0.81800 (10)0.17703 (12)0.0265 (3)
H40.3052 (10)0.4636 (11)0.1932 (12)0.019 (3)*
H70.2440 (11)0.2955 (11)0.1137 (13)0.022 (3)*
H120.1098 (12)0.3537 (13)0.2398 (14)0.032 (4)*
H130.0043 (12)0.2189 (12)0.3977 (14)0.031 (4)*
H140.0258 (13)0.0283 (13)0.3314 (14)0.037 (4)*
H150.0595 (12)0.0253 (12)0.1099 (14)0.028 (3)*
H160.1677 (12)0.1098 (13)0.0481 (14)0.033 (4)*
H210.4754 (13)0.5213 (13)0.3662 (15)0.037 (4)*
H220.5852 (13)0.5041 (14)0.3240 (15)0.039 (4)*
H230.5723 (13)0.6179 (13)0.3999 (15)0.037 (4)*
H240.5270 (13)0.7189 (13)0.0676 (15)0.036 (4)*
H250.6155 (13)0.6195 (13)0.1459 (15)0.037 (4)*
H260.6048 (14)0.7397 (14)0.2184 (16)0.046 (4)*
H310.3833 (11)0.5781 (11)0.0035 (13)0.022 (3)*
H320.4467 (12)0.4718 (13)0.0945 (14)0.031 (4)*
H510.1445 (11)0.5940 (12)0.1095 (13)0.025 (3)*
H520.2051 (11)0.6517 (12)0.0143 (13)0.027 (3)*
H610.3023 (12)0.5813 (13)0.3674 (14)0.033 (4)*
H620.1970 (13)0.6676 (13)0.3462 (14)0.037 (4)*
H630.3271 (12)0.7111 (12)0.4193 (14)0.029 (4)*
H640.1359 (13)0.8067 (12)0.1584 (14)0.033 (4)*
H650.2509 (13)0.8741 (13)0.2497 (15)0.036 (4)*
H660.2311 (12)0.8528 (13)0.0962 (15)0.034 (4)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0310 (4)0.0203 (4)0.0280 (4)0.0068 (3)0.0076 (3)0.0086 (3)
N10.0220 (4)0.0162 (4)0.0183 (4)0.0018 (3)0.0059 (3)0.0029 (3)
N20.0238 (5)0.0203 (5)0.0184 (4)0.0018 (4)0.0042 (4)0.0022 (3)
C20.0189 (5)0.0215 (5)0.0190 (5)0.0013 (4)0.0041 (4)0.0040 (4)
C30.0210 (5)0.0196 (5)0.0176 (5)0.0020 (4)0.0038 (4)0.0034 (4)
C40.0242 (5)0.0172 (5)0.0153 (5)0.0021 (4)0.0034 (4)0.0019 (4)
C50.0194 (5)0.0206 (5)0.0194 (5)0.0013 (4)0.0062 (4)0.0015 (4)
C60.0217 (5)0.0190 (5)0.0195 (5)0.0001 (4)0.0088 (4)0.0016 (4)
C70.0202 (5)0.0198 (5)0.0186 (5)0.0006 (4)0.0039 (4)0.0011 (4)
C110.0183 (5)0.0188 (5)0.0211 (5)0.0008 (4)0.0048 (4)0.0030 (4)
C120.0221 (5)0.0222 (6)0.0220 (5)0.0009 (4)0.0068 (4)0.0019 (4)
C130.0221 (5)0.0292 (6)0.0207 (5)0.0018 (4)0.0058 (4)0.0051 (4)
C140.0210 (5)0.0250 (6)0.0281 (6)0.0020 (4)0.0069 (4)0.0102 (5)
C150.0245 (5)0.0178 (5)0.0333 (6)0.0001 (4)0.0082 (5)0.0032 (5)
C160.0235 (5)0.0198 (5)0.0245 (5)0.0017 (4)0.0040 (4)0.0007 (4)
C210.0287 (6)0.0283 (6)0.0202 (5)0.0058 (5)0.0007 (4)0.0034 (5)
C220.0218 (5)0.0395 (7)0.0278 (6)0.0060 (5)0.0090 (5)0.0095 (5)
C610.0325 (6)0.0276 (6)0.0206 (5)0.0032 (5)0.0126 (5)0.0023 (5)
C620.0294 (6)0.0234 (6)0.0276 (6)0.0057 (5)0.0114 (5)0.0020 (5)
Geometric parameters (Å, º) top
O1—N11.2888 (11)C12—C131.3887 (15)
N1—C21.4988 (14)C12—H120.971 (15)
N1—C61.4941 (13)C13—C141.3899 (17)
N2—C41.4683 (13)C13—H130.960 (14)
N2—C71.2659 (14)C14—C151.3902 (17)
C2—C221.5323 (16)C14—H140.979 (15)
C2—C31.5341 (14)C15—C161.3914 (16)
C2—C211.5361 (15)C15—H150.978 (14)
C3—C41.5247 (15)C16—H160.961 (14)
C3—H311.015 (13)C21—H211.012 (16)
C3—H320.980 (15)C21—H220.970 (16)
C4—C51.5228 (15)C21—H230.975 (16)
C4—H40.999 (12)C22—H241.003 (15)
C5—C61.5314 (14)C22—H250.992 (16)
C5—H511.004 (13)C22—H260.990 (17)
C5—H521.013 (13)C61—H610.991 (15)
C6—C621.5311 (15)C61—H621.003 (16)
C6—C611.5380 (15)C61—H630.991 (14)
C7—C111.4779 (14)C62—H641.013 (15)
C7—H71.002 (13)C62—H650.988 (15)
C11—C161.3966 (16)C62—H661.018 (15)
C11—C121.3996 (15)
O1···O1i5.5398 (9)O1···H32ii2.422 (15)
O1···O1ii6.0841 (9)O1···H22ii2.657 (16)
O1···C3ii3.3134 (14)O1···H24i2.755 (15)
O1···C21ii3.3654 (16)O1···H31i3.028 (13)
O1—N1—C6115.29 (8)C13—C12—C11120.04 (11)
O1—N1—C2115.84 (8)C13—C12—H12120.5 (8)
C6—N1—C2124.31 (8)C11—C12—H12119.5 (8)
C7—N2—C4116.84 (9)C12—C13—C14120.56 (11)
N1—C2—C22107.47 (9)C12—C13—H13119.2 (8)
N1—C2—C3110.01 (8)C14—C13—H13120.2 (8)
C22—C2—C3108.78 (9)C13—C14—C15119.71 (10)
N1—C2—C21108.58 (9)C13—C14—H14122.5 (9)
C22—C2—C21109.85 (10)C15—C14—H14117.8 (9)
C3—C2—C21112.05 (9)C14—C15—C16120.01 (11)
C4—C3—C2113.73 (9)C14—C15—H15120.0 (8)
C4—C3—H31108.5 (7)C16—C15—H15120.0 (8)
C2—C3—H31109.3 (7)C15—C16—C11120.53 (11)
C4—C3—H32109.7 (8)C15—C16—H16120.2 (9)
C2—C3—H32108.3 (8)C11—C16—H16119.2 (9)
H31—C3—H32107.0 (11)C2—C21—H21111.9 (9)
N2—C4—C5108.33 (9)C2—C21—H22110.0 (9)
N2—C4—C3108.93 (8)H21—C21—H22108.9 (12)
C5—C4—C3108.39 (9)C2—C21—H23108.6 (9)
N2—C4—H4110.2 (7)H21—C21—H23107.3 (12)
C5—C4—H4111.1 (7)H22—C21—H23110.1 (13)
C3—C4—H4109.8 (7)C2—C22—H24111.7 (9)
C4—C5—C6113.87 (9)C2—C22—H25109.1 (9)
C4—C5—H51110.5 (8)H24—C22—H25108.5 (12)
C6—C5—H51108.3 (8)C2—C22—H26110.5 (10)
C4—C5—H52107.4 (8)H24—C22—H26106.2 (12)
C6—C5—H52108.9 (8)H25—C22—H26110.8 (12)
H51—C5—H52107.7 (10)C6—C61—H61112.0 (8)
N1—C6—C62107.47 (9)C6—C61—H62109.2 (8)
N1—C6—C5109.87 (8)H61—C61—H62107.9 (12)
C62—C6—C5109.47 (9)C6—C61—H63110.8 (8)
N1—C6—C61109.27 (9)H61—C61—H63107.8 (11)
C62—C6—C61109.08 (9)H62—C61—H63109.0 (11)
C5—C6—C61111.57 (9)C6—C62—H64108.4 (8)
N2—C7—C11122.87 (10)C6—C62—H65111.6 (8)
N2—C7—H7122.8 (7)H64—C62—H65109.3 (12)
C11—C7—H7114.4 (7)C6—C62—H66111.4 (8)
C16—C11—C12119.14 (10)H64—C62—H66109.5 (11)
C16—C11—C7119.52 (10)H65—C62—H66106.7 (11)
C12—C11—C7121.32 (10)
O1—N1—C2—C3170.02 (9)O1—N1—C6—C6250.63 (11)
O1—N1—C6—C5169.67 (8)C2—N1—C6—C62154.40 (9)
C6—N1—C2—C335.14 (13)O1—N1—C6—C6167.61 (12)
C2—N1—C6—C535.36 (13)C2—N1—C6—C6187.36 (11)
N1—C2—C3—C445.73 (12)C4—C5—C6—C62164.18 (9)
C4—C5—C6—N146.37 (12)C4—C5—C6—C6174.98 (12)
C2—C3—C4—C559.46 (11)C4—N2—C7—C11178.84 (9)
C3—C4—C5—C659.89 (11)N2—C7—C11—C16177.42 (11)
C2—C3—C4—N2177.14 (8)N2—C7—C11—C121.21 (17)
N2—C4—C5—C6177.95 (9)C16—C11—C12—C130.82 (16)
C7—N2—C4—C3112.82 (11)C7—C11—C12—C13177.81 (10)
C7—N2—C4—C5129.47 (10)C11—C12—C13—C140.10 (17)
O1—N1—C2—C2251.74 (12)C12—C13—C14—C150.50 (17)
C6—N1—C2—C22153.42 (9)C13—C14—C15—C160.36 (17)
O1—N1—C2—C2167.03 (12)C14—C15—C16—C110.37 (17)
C6—N1—C2—C2187.80 (11)C12—C11—C16—C150.96 (17)
C22—C2—C3—C4163.20 (9)C7—C11—C16—C15177.70 (10)
C21—C2—C3—C475.15 (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
C17H25N2OSDx = 1.140 Mg m3
Mr = 305.46Melting point: not measured K
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
a = 13.5737 (18) ÅCell parameters from 25 reflections
b = 11.8796 (18) Åθ = 12.7–17.4°
c = 11.1628 (16) ŵ = 0.18 mm1
β = 98.760 (11)°T = 296 K
V = 1779.0 (4) Å3Prism, orange
Z = 40.50 × 0.35 × 0.25 mm
F(000) = 660.00
Data collection top
Rigaku AFC7R
diffractometer
Rint = 0.021
Radiation source: Rigaku rotating anodeθmax = 27.5°, θmin = 2.3°
Graphite monochromatorh = 1717
ω–2θ scansk = 150
4304 measured reflectionsl = 014
4091 independent reflections3 standard reflections every 150 reflections
2979 reflections with I > 2σ(I) intensity decay: 0.0%
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: difmap and geom
R[F2 > 2σ(F2)] = 0.040All H-atom parameters refined
wR(F2) = 0.122Calculated w = 1/[σ2(Fo2) + (0.0512P)2 + 0.3325P]
where P = (Fo2 + 2Fc2)/3
S = 1.02(Δ/σ)max = 0.001
4091 reflectionsΔρmax = 0.23 e Å3
291 parametersΔρmin = 0.26 e Å3
0 restraintsExtinction correction: SHELXL-97 (Sheldrick, 1997), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0182 (16)
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
xyzUiso*/Ueq
S10.00162 (4)0.02068 (5)0.25419 (5)0.0844 (2)
O10.46260 (11)0.79174 (11)0.31102 (13)0.0891 (4)
N10.41586 (11)0.71109 (11)0.25022 (12)0.0600 (3)
N20.26132 (10)0.43938 (11)0.06283 (11)0.0605 (3)
C20.47918 (12)0.61991 (15)0.21142 (15)0.0643 (4)
C30.41595 (12)0.54164 (15)0.12193 (15)0.0593 (4)
C40.31724 (13)0.50953 (13)0.15815 (14)0.0578 (4)
C50.25828 (13)0.61645 (15)0.16932 (17)0.0622 (4)
C60.30903 (14)0.69928 (14)0.26370 (15)0.0643 (4)
C70.25185 (11)0.33698 (13)0.08471 (15)0.0563 (4)
C110.19525 (11)0.25896 (12)0.00233 (14)0.0533 (3)
C120.15500 (13)0.29465 (14)0.11764 (15)0.0598 (4)
C130.09536 (13)0.22453 (15)0.19658 (17)0.0651 (4)
C140.07558 (11)0.11579 (13)0.16192 (16)0.0605 (4)
C150.11745 (14)0.07852 (14)0.04787 (18)0.0697 (5)
C160.17698 (13)0.14949 (14)0.03093 (17)0.0668 (4)
C170.03879 (18)0.0965 (2)0.3911 (2)0.0909 (7)
C210.5274 (2)0.5564 (2)0.3249 (2)0.0974 (8)
C220.55840 (18)0.6752 (3)0.1474 (3)0.1001 (9)
C610.3010 (2)0.6612 (2)0.3924 (2)0.0924 (7)
C620.2608 (2)0.8159 (2)0.2399 (3)0.0926 (7)
H40.3256 (14)0.4711 (15)0.2354 (18)0.074 (5)*
H70.2781 (13)0.3074 (16)0.1651 (17)0.072 (5)*
H120.1686 (12)0.3729 (15)0.1421 (15)0.068 (5)*
H130.0711 (15)0.2501 (16)0.2775 (18)0.083 (6)*
H150.1035 (15)0.0073 (18)0.0185 (19)0.088 (6)*
H160.2066 (14)0.1231 (16)0.1116 (18)0.085 (6)*
H210.475 (2)0.517 (2)0.370 (2)0.112 (9)*
H220.570 (2)0.507 (2)0.304 (2)0.115 (9)*
H230.5624 (17)0.608 (2)0.379 (2)0.109 (8)*
H240.527 (2)0.717 (2)0.075 (3)0.130 (11)*
H250.604 (2)0.611 (3)0.127 (3)0.151 (11)*
H260.597 (2)0.719 (2)0.205 (2)0.114 (8)*
H310.4018 (11)0.5779 (13)0.0419 (15)0.056 (4)*
H320.4553 (14)0.4802 (17)0.1126 (17)0.076 (5)*
H510.1941 (15)0.5976 (16)0.1939 (16)0.082 (6)*
H520.2472 (13)0.6548 (16)0.0851 (18)0.079 (5)*
H610.3311 (15)0.5878 (19)0.4123 (18)0.081 (6)*
H620.2268 (18)0.660 (2)0.404 (2)0.107 (8)*
H630.343 (2)0.712 (2)0.454 (2)0.123 (9)*
H640.191 (2)0.804 (2)0.242 (2)0.119 (9)*
H650.2836 (18)0.866 (2)0.307 (2)0.113 (8)*
H660.278 (2)0.849 (2)0.154 (3)0.142 (10)*
H710.020 (2)0.117 (2)0.430 (2)0.128 (9)*
H720.0752 (19)0.173 (2)0.372 (2)0.125 (9)*
H730.0835 (17)0.0485 (19)0.436 (2)0.100 (7)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.0703 (3)0.0738 (3)0.1028 (4)0.0136 (2)0.0067 (3)0.0318 (3)
O10.1036 (10)0.0652 (8)0.0958 (10)0.0257 (7)0.0070 (8)0.0334 (7)
N10.0720 (8)0.0488 (7)0.0583 (7)0.0103 (6)0.0068 (6)0.0134 (6)
N20.0741 (8)0.0498 (7)0.0524 (7)0.0087 (6)0.0074 (6)0.0048 (5)
C20.0590 (9)0.0672 (10)0.0628 (9)0.0008 (7)0.0033 (7)0.0191 (8)
C30.0595 (9)0.0570 (9)0.0576 (9)0.0045 (7)0.0031 (7)0.0168 (7)
C40.0740 (10)0.0483 (8)0.0467 (8)0.0091 (7)0.0051 (7)0.0038 (6)
C50.0599 (9)0.0629 (10)0.0649 (10)0.0069 (7)0.0131 (8)0.0091 (8)
C60.0767 (11)0.0577 (9)0.0615 (9)0.0056 (8)0.0206 (8)0.0128 (7)
C70.0582 (8)0.0508 (8)0.0555 (8)0.0018 (6)0.0053 (7)0.0019 (7)
C110.0517 (7)0.0457 (7)0.0594 (8)0.0013 (6)0.0018 (6)0.0055 (6)
C120.0670 (9)0.0495 (8)0.0591 (9)0.0036 (7)0.0025 (7)0.0046 (7)
C130.0691 (10)0.0618 (9)0.0598 (9)0.0031 (8)0.0042 (8)0.0097 (8)
C140.0489 (8)0.0565 (8)0.0741 (10)0.0004 (6)0.0026 (7)0.0198 (8)
C150.0712 (10)0.0442 (8)0.0897 (12)0.0048 (7)0.0009 (9)0.0042 (8)
C160.0713 (10)0.0506 (8)0.0729 (11)0.0011 (7)0.0077 (8)0.0001 (8)
C170.0736 (13)0.122 (2)0.0748 (13)0.0213 (13)0.0029 (10)0.0357 (13)
C210.1011 (18)0.0918 (17)0.0840 (15)0.0198 (15)0.0354 (14)0.0221 (13)
C220.0672 (13)0.135 (2)0.0988 (18)0.0323 (14)0.0159 (12)0.0432 (18)
C610.127 (2)0.0910 (17)0.0651 (12)0.0225 (15)0.0346 (13)0.0150 (11)
C620.1033 (18)0.0700 (13)0.1089 (19)0.0127 (12)0.0305 (15)0.0216 (13)
Geometric parameters (Å, º) top
S1—C141.7626 (15)C12—C131.381 (2)
S1—C171.780 (3)C12—H120.994 (17)
O1—N11.2845 (16)C13—C141.386 (2)
N1—C21.488 (2)C13—H130.96 (2)
N1—C61.487 (2)C14—C151.385 (2)
N2—C41.4687 (18)C15—C161.386 (2)
N2—C71.251 (2)C15—H150.94 (2)
C2—C221.527 (3)C16—H160.98 (2)
C2—C31.529 (2)C17—H711.00 (3)
C2—C211.533 (3)C17—H721.07 (3)
C3—C41.506 (2)C17—H730.92 (2)
C3—H310.984 (16)C21—H211.04 (3)
C3—H320.92 (2)C21—H220.88 (3)
C4—C51.517 (2)C21—H230.94 (3)
C4—H40.968 (19)C22—H240.99 (3)
C5—C61.527 (2)C22—H251.03 (3)
C5—H510.978 (19)C22—H260.92 (3)
C5—H521.035 (19)C61—H610.98 (2)
C6—C611.525 (3)C61—H621.03 (2)
C6—C621.538 (3)C61—H631.02 (3)
C7—C111.472 (2)C62—H640.97 (3)
C7—H70.979 (18)C62—H650.97 (2)
C11—C161.385 (2)C62—H661.10 (3)
C11—C121.386 (2)
O1···O1i5.6688 (9)O1···H32ii2.59 (2)
O1···O1ii6.2120 (12)O1···H22ii2.87 (3)
O1···C3ii3.423 (2)O1···H24i2.95 (3)
O1···C21ii3.503 (3)O1···H31i3.220 (16)
C14—S1—C17104.07 (10)C11—C12—H12118.6 (10)
O1—N1—C6115.32 (13)C12—C13—C14120.22 (16)
O1—N1—C2115.86 (13)C12—C13—H13119.5 (12)
C6—N1—C2125.19 (12)C14—C13—H13120.2 (12)
C7—N2—C4117.87 (13)C15—C14—C13118.98 (14)
N1—C2—C22107.58 (18)C15—C14—S1117.15 (13)
N1—C2—C3109.96 (13)C13—C14—S1123.87 (14)
C22—C2—C3108.73 (15)C14—C15—C16120.45 (16)
N1—C2—C21108.09 (17)C14—C15—H15122.2 (13)
C22—C2—C21110.8 (2)C16—C15—H15117.2 (13)
C3—C2—C21111.55 (17)C11—C16—C15120.79 (16)
C4—C3—C2114.35 (13)C11—C16—H16118.8 (11)
C4—C3—H31107.2 (9)C15—C16—H16120.4 (11)
C2—C3—H31109.9 (9)S1—C17—H71111.3 (15)
C4—C3—H32112.6 (12)S1—C17—H72109.5 (14)
C2—C3—H32106.2 (12)H71—C17—H72107 (2)
H31—C3—H32106.3 (15)S1—C17—H73103.4 (14)
N2—C4—C3109.38 (13)H71—C17—H73115 (2)
N2—C4—C5108.29 (13)H72—C17—H73110.4 (19)
C3—C4—C5108.19 (13)C2—C21—H21112.6 (14)
N2—C4—H4110.8 (11)C2—C21—H22109.0 (18)
C3—C4—H4111.7 (11)H21—C21—H22110 (2)
C5—C4—H4108.3 (11)C2—C21—H23108.9 (15)
C4—C5—C6114.09 (14)H21—C21—H23107 (2)
C4—C5—H51109.6 (11)H22—C21—H23109 (2)
C6—C5—H51106.4 (11)C2—C22—H24110.5 (17)
C4—C5—H52107.4 (11)C2—C22—H25105.9 (17)
C6—C5—H52109.3 (11)H24—C22—H25113 (2)
H51—C5—H52110.1 (15)C2—C22—H26106.7 (16)
N1—C6—C61109.50 (18)H24—C22—H26114 (2)
N1—C6—C5109.60 (13)H25—C22—H26106 (2)
C61—C6—C5111.67 (16)C6—C61—H61113.1 (12)
N1—C6—C62107.06 (16)C6—C61—H62109.1 (13)
C61—C6—C62109.88 (18)H61—C61—H62110.3 (18)
C5—C6—C62109.01 (17)C6—C61—H63110.1 (14)
N2—C7—C11122.83 (14)H61—C61—H63102.2 (18)
N2—C7—H7119.6 (11)H62—C61—H63111.9 (19)
C11—C7—H7117.4 (11)C6—C62—H64104.9 (16)
C16—C11—C12118.35 (14)C6—C62—H65109.9 (15)
C16—C11—C7120.73 (14)H64—C62—H65106 (2)
C12—C11—C7120.85 (14)C6—C62—H66109.6 (15)
C13—C12—C11121.19 (15)H64—C62—H66114 (2)
C13—C12—H12120.2 (10)H65—C62—H66112 (2)
O1—N1—C2—C3169.95 (15)O1—N1—C6—C6251.1 (2)
O1—N1—C6—C5169.16 (14)C2—N1—C6—C62151.41 (17)
C6—N1—C2—C332.6 (2)C4—C5—C6—C6175.9 (2)
C2—N1—C6—C533.3 (2)C4—C5—C6—C62162.54 (17)
N1—C2—C3—C444.4 (2)C4—N2—C7—C11178.33 (14)
C4—C5—C6—N145.7 (2)N2—C7—C11—C16172.43 (17)
C2—C3—C4—C559.37 (18)N2—C7—C11—C124.5 (3)
C3—C4—C5—C660.16 (18)C16—C11—C12—C132.1 (3)
C2—C3—C4—N2177.13 (14)C7—C11—C12—C13174.95 (16)
N2—C4—C5—C6178.61 (14)C11—C12—C13—C140.8 (3)
C7—N2—C4—C3108.56 (17)C12—C13—C14—C150.8 (3)
C7—N2—C4—C5133.75 (16)C12—C13—C14—S1178.53 (13)
O1—N1—C2—C2251.7 (2)C17—S1—C14—C15179.08 (15)
C6—N1—C2—C22150.90 (18)C17—S1—C14—C131.60 (18)
O1—N1—C2—C2168.1 (2)C13—C14—C15—C160.9 (3)
C6—N1—C2—C2189.3 (2)S1—C14—C15—C16178.40 (14)
C22—C2—C3—C4161.99 (19)C12—C11—C16—C151.9 (3)
C21—C2—C3—C475.5 (2)C7—C11—C16—C15175.14 (16)
O1—N1—C6—C6168.0 (2)C14—C15—C16—C110.4 (3)
C2—N1—C6—C6189.50 (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
C15H22N3OF(000) = 564.00
Mr = 260.36Dx = 1.153 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
a = 12.425 (5) ÅCell parameters from 25 reflections
b = 11.598 (4) Åθ = 12.7–17.4°
c = 11.038 (5) ŵ = 0.07 mm1
β = 109.53 (4)°T = 297 K
V = 1499.3 (10) Å3Prism, orange
Z = 40.20 × 0.20 × 0.20 mm
Data collection top
Rigaku AFC5R
diffractometer
Rint = 0.020
Radiation source: Rigaku rotating anodeθmax = 27.5°, θmin = 2.5°
Graphite monochromatorh = 1615
ω–2θ scansk = 015
3608 measured reflectionsl = 014
3432 independent reflections3 standard reflections every 100 reflections
2096 reflections with I > 2σ(I) intensity decay: 0.1%
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: difmap and geom
R[F2 > 2σ(F2)] = 0.049All H-atom parameters refined
wR(F2) = 0.135Calculated w = 1/[σ2(Fo2) + (0.058P)2 + 0.2599P]
where P = (Fo2 + 2Fc2)/3
S = 0.98(Δ/σ)max = 0.002
3432 reflectionsΔρmax = 0.15 e Å3
261 parametersΔρmin = 0.12 e Å3
0 restraintsExtinction correction: SHELXL-97 (Sheldrick, 1997), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.038 (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
xyzUiso*/Ueq
O10.46505 (12)0.78860 (11)0.32658 (13)0.0650 (4)
N10.40835 (12)0.71122 (12)0.24780 (13)0.0443 (4)
N20.22071 (13)0.45312 (13)0.00520 (13)0.0496 (4)
N30.08599 (17)0.08994 (16)0.2040 (2)0.0828 (6)
C20.47748 (14)0.61872 (15)0.21527 (16)0.0466 (4)
C30.40218 (15)0.54721 (16)0.10254 (17)0.0454 (4)
C40.28812 (15)0.51259 (15)0.11344 (16)0.0441 (4)
C50.22439 (16)0.62034 (16)0.12696 (18)0.0466 (4)
C60.28714 (15)0.69687 (15)0.24096 (16)0.0450 (4)
C70.21370 (15)0.34642 (17)0.00312 (18)0.0499 (5)
C110.14925 (15)0.27791 (15)0.11654 (17)0.0499 (5)
C120.09159 (17)0.3275 (2)0.23400 (19)0.0568 (5)
C130.03221 (18)0.2568 (2)0.3345 (2)0.0665 (6)
C140.03225 (19)0.1405 (2)0.3149 (2)0.0721 (7)
C160.14359 (19)0.15965 (19)0.1079 (2)0.0702 (6)
C210.5317 (2)0.5441 (2)0.3348 (2)0.0668 (6)
C220.5702 (2)0.6771 (3)0.1752 (3)0.0713 (7)
C610.2840 (2)0.6460 (2)0.3678 (2)0.0606 (6)
C620.2319 (2)0.8162 (2)0.2199 (3)0.0631 (6)
H40.2982 (13)0.4591 (14)0.1863 (16)0.039 (4)*
H70.2502 (17)0.3041 (18)0.074 (2)0.067 (6)*
H120.0932 (16)0.4083 (19)0.2439 (18)0.063 (6)*
H130.007 (2)0.2870 (19)0.414 (2)0.080 (7)*
H140.0077 (18)0.090 (2)0.381 (2)0.080 (7)*
H160.183 (2)0.125 (2)0.026 (2)0.083 (7)*
H210.472 (2)0.499 (2)0.358 (2)0.095 (9)*
H220.583 (2)0.493 (2)0.320 (2)0.080 (7)*
H230.5723 (17)0.5916 (18)0.406 (2)0.067 (6)*
H240.5387 (19)0.721 (2)0.098 (2)0.077 (7)*
H250.619 (2)0.618 (2)0.153 (2)0.104 (9)*
H260.623 (2)0.724 (2)0.247 (2)0.083 (7)*
H310.3875 (14)0.5912 (15)0.0224 (17)0.047 (5)*
H320.4456 (15)0.4786 (17)0.0933 (17)0.054 (5)*
H510.1500 (16)0.6015 (16)0.1351 (17)0.060 (5)*
H520.2098 (15)0.6630 (16)0.0478 (18)0.054 (5)*
H610.3117 (17)0.565 (2)0.3784 (19)0.067 (6)*
H620.205 (2)0.643 (2)0.368 (2)0.091 (8)*
H630.3339 (18)0.6895 (18)0.440 (2)0.070 (6)*
H640.148 (2)0.8059 (19)0.204 (2)0.077 (7)*
H650.2633 (19)0.865 (2)0.290 (2)0.080 (7)*
H660.2381 (18)0.853 (2)0.143 (2)0.076 (7)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0709 (9)0.0530 (8)0.0679 (9)0.0191 (7)0.0190 (7)0.0245 (7)
N10.0517 (8)0.0387 (8)0.0410 (7)0.0067 (7)0.0135 (6)0.0071 (6)
N20.0581 (9)0.0438 (9)0.0401 (8)0.0085 (7)0.0072 (7)0.0060 (6)
N30.0742 (12)0.0538 (11)0.0978 (15)0.0002 (9)0.0014 (11)0.0300 (11)
C20.0447 (10)0.0512 (11)0.0401 (9)0.0020 (8)0.0093 (7)0.0075 (8)
C30.0512 (10)0.0443 (10)0.0373 (9)0.0047 (8)0.0101 (8)0.0062 (8)
C40.0554 (11)0.0374 (9)0.0347 (8)0.0051 (8)0.0085 (7)0.0021 (7)
C50.0453 (10)0.0494 (11)0.0435 (10)0.0042 (8)0.0129 (8)0.0027 (8)
C60.0492 (10)0.0431 (10)0.0447 (9)0.0026 (8)0.0183 (8)0.0060 (8)
C70.0516 (11)0.0448 (11)0.0467 (10)0.0006 (8)0.0077 (9)0.0034 (8)
C110.0447 (10)0.0466 (10)0.0545 (10)0.0000 (8)0.0115 (8)0.0117 (8)
C120.0564 (11)0.0586 (13)0.0522 (11)0.0028 (10)0.0139 (9)0.0088 (10)
C130.0532 (12)0.0864 (17)0.0526 (12)0.0040 (11)0.0080 (10)0.0150 (12)
C140.0542 (12)0.0752 (16)0.0760 (15)0.0022 (12)0.0071 (11)0.0393 (14)
C160.0663 (14)0.0506 (12)0.0755 (15)0.0037 (10)0.0005 (12)0.0129 (11)
C210.0670 (15)0.0715 (15)0.0470 (11)0.0175 (13)0.0006 (11)0.0066 (11)
C220.0505 (12)0.102 (2)0.0640 (15)0.0184 (13)0.0224 (11)0.0215 (14)
C610.0734 (15)0.0653 (15)0.0491 (11)0.0127 (12)0.0284 (11)0.0075 (10)
C620.0702 (15)0.0506 (12)0.0709 (15)0.0084 (11)0.0270 (12)0.0089 (11)
Geometric parameters (Å, º) top
O1—N11.2839 (17)C7—H70.96 (2)
N1—C21.491 (2)C11—C161.378 (3)
N1—C61.492 (2)C11—C121.380 (3)
N2—C41.469 (2)C12—C131.378 (3)
N2—C71.241 (2)C12—H120.94 (2)
N3—C141.319 (3)C13—C141.365 (4)
N3—C161.335 (3)C13—H130.92 (2)
C2—C221.523 (3)C14—H140.94 (2)
C2—C31.528 (2)C16—H160.96 (2)
C2—C211.533 (3)C21—H211.01 (3)
C3—C41.516 (3)C21—H220.93 (2)
C3—H310.984 (18)C21—H230.95 (2)
C3—H320.986 (19)C22—H240.96 (2)
C4—C51.513 (3)C22—H251.00 (3)
C4—H40.990 (17)C22—H261.00 (2)
C5—C61.524 (2)C61—H611.00 (2)
C5—H510.983 (19)C61—H620.98 (3)
C5—H520.967 (19)C61—H630.97 (2)
C6—C621.528 (3)C62—H641.00 (2)
C6—C611.532 (3)C62—H650.94 (2)
C7—C111.473 (2)C62—H660.98 (2)
O1···O1i5.591 (2)O1···H32ii2.49 (2)
O1···O1ii6.183 (2)O1···H22ii2.82 (2)
O1···O1iii6.102 (3)O1···H24i2.82 (2)
O1···C3ii3.386 (2)O1···H31i2.99 (2)
O1···C21ii3.464 (3)
O1—N1—C2115.86 (14)C16—C11—C7120.27 (19)
O1—N1—C6115.36 (13)C12—C11—C7122.54 (18)
C2—N1—C6124.10 (13)C13—C12—C11118.6 (2)
C7—N2—C4118.30 (16)C13—C12—H12121.6 (12)
C14—N3—C16116.0 (2)C11—C12—H12119.8 (12)
N1—C2—C22107.60 (17)C14—C13—C12119.2 (2)
N1—C2—C3109.97 (14)C14—C13—H13120.1 (15)
C22—C2—C3108.74 (16)C12—C13—H13120.7 (15)
N1—C2—C21108.79 (16)N3—C14—C13124.0 (2)
C22—C2—C21110.08 (19)N3—C14—H14114.9 (14)
C3—C2—C21111.58 (17)C13—C14—H14121.1 (14)
C4—C3—C2114.42 (15)N3—C16—C11125.0 (2)
C4—C3—H31108.2 (10)N3—C16—H16117.5 (14)
C2—C3—H31109.2 (10)C11—C16—H16117.5 (14)
C4—C3—H32110.7 (10)C2—C21—H21111.1 (14)
C2—C3—H32108.4 (10)C2—C21—H22109.7 (14)
H31—C3—H32105.6 (15)H21—C21—H22109 (2)
N2—C4—C5108.32 (14)C2—C21—H23109.9 (13)
N2—C4—C3108.85 (14)H21—C21—H23109 (2)
C5—C4—C3108.84 (15)H22—C21—H23108.1 (18)
N2—C4—H4108.0 (9)C2—C22—H24111.9 (14)
C5—C4—H4111.5 (9)C2—C22—H25110.1 (15)
C3—C4—H4111.3 (9)H24—C22—H25105 (2)
C4—C5—C6114.97 (15)C2—C22—H26112.0 (14)
C4—C5—H51111.4 (11)H24—C22—H26112.3 (19)
C6—C5—H51106.9 (11)H25—C22—H26105.4 (19)
C4—C5—H52106.2 (11)C6—C61—H61111.0 (12)
C6—C5—H52109.8 (11)C6—C61—H62110.3 (14)
H51—C5—H52107.4 (15)H61—C61—H62105.7 (19)
N1—C6—C5109.63 (14)C6—C61—H63110.3 (12)
N1—C6—C62107.54 (16)H61—C61—H63107.1 (17)
C5—C6—C62108.78 (17)H62—C61—H63112.3 (19)
N1—C6—C61109.30 (16)C6—C62—H64107.8 (13)
C5—C6—C61111.59 (16)C6—C62—H65112.5 (14)
C62—C6—C61109.91 (18)H64—C62—H65109.9 (19)
N2—C7—C11122.93 (18)C6—C62—H66111.5 (13)
N2—C7—H7120.9 (12)H64—C62—H66106.1 (18)
C11—C7—H7116.2 (12)H65—C62—H66108.9 (19)
C16—C11—C12117.18 (19)
O1—N1—C2—C3169.04 (14)O1—N1—C6—C6251.0 (2)
O1—N1—C6—C5169.11 (14)C2—N1—C6—C62154.35 (16)
C6—N1—C2—C336.4 (2)O1—N1—C6—C6168.29 (19)
C2—N1—C6—C536.2 (2)C2—N1—C6—C6186.37 (19)
N1—C2—C3—C445.6 (2)C4—C5—C6—C62162.94 (17)
C4—C5—C6—N145.6 (2)C4—C5—C6—C6175.6 (2)
C2—C3—C4—C557.4 (2)C4—N2—C7—C11179.51 (16)
C3—C4—C5—C657.7 (2)N2—C7—C11—C16179.3 (2)
C2—C3—C4—N2175.29 (14)N2—C7—C11—C120.0 (3)
N2—C4—C5—C6175.87 (15)C16—C11—C12—C130.2 (3)
C7—N2—C4—C3102.9 (2)C7—C11—C12—C13179.13 (18)
C7—N2—C4—C5138.93 (18)C11—C12—C13—C140.0 (3)
O1—N1—C2—C2250.75 (19)C16—N3—C14—C130.6 (4)
C6—N1—C2—C22154.70 (16)C12—C13—C14—N30.2 (4)
O1—N1—C2—C2168.5 (2)C14—N3—C16—C110.8 (4)
C6—N1—C2—C2186.1 (2)C12—C11—C16—N30.6 (3)
C22—C2—C3—C4163.18 (19)C7—C11—C16—N3178.7 (2)
C21—C2—C3—C475.2 (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
C17H25N2OF(000) = 596.00
Mr = 273.40Dx = 1.120 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
a = 12.490 (3) ÅCell parameters from 25 reflections
b = 11.597 (5) Åθ = 17.3–17.5°
c = 11.280 (6) ŵ = 0.07 mm1
β = 97.12 (3)°T = 294 K
V = 1621.3 (11) Å3Plate, orange
Z = 40.40 × 0.40 × 0.10 mm
Data collection top
Rigaku AFC7R
diffractometer
Rint = 0.022
Radiation source: Rigaku rotating anodeθmax = 27.5°, θmin = 2.4°
Graphite monochromatorh = 1616
ω–2θ scansk = 150
3911 measured reflectionsl = 014
3722 independent reflections3 standard reflections every 150 reflections
2582 reflections with I > 2σ(I) intensity decay: 2.4%
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: difmap and geom
R[F2 > 2σ(F2)] = 0.050All H-atom parameters refined
wR(F2) = 0.162Calculated w = 1/[σ2(Fo2) + (0.0786P)2 + 0.2899P]
where P = (Fo2 + 2Fc2)/3
S = 1.04(Δ/σ)max = 0.004
3722 reflectionsΔρmax = 0.20 e Å3
282 parametersΔρmin = 0.15 e Å3
0 restraintsExtinction correction: SHELXL-97 (Sheldrick, 1997), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.010 (2)
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
xyzUiso*/Ueq
O10.47665 (10)0.78157 (11)0.14265 (12)0.0663 (4)
N10.42132 (10)0.70948 (11)0.19654 (12)0.0476 (3)
N20.23830 (12)0.47052 (12)0.37066 (12)0.0539 (4)
C20.48471 (12)0.61885 (14)0.26858 (14)0.0509 (4)
C30.41239 (13)0.55485 (15)0.34689 (15)0.0501 (4)
C40.30318 (13)0.52061 (13)0.28352 (15)0.0492 (4)
C50.24614 (13)0.62848 (15)0.23262 (16)0.0503 (4)
C60.30651 (13)0.69569 (14)0.14480 (14)0.0494 (4)
C70.23144 (13)0.36302 (14)0.37570 (15)0.0497 (4)
C110.16801 (12)0.30377 (13)0.45921 (14)0.0487 (4)
C120.10994 (16)0.36414 (17)0.53603 (18)0.0626 (5)
C130.04934 (17)0.30621 (18)0.61150 (19)0.0669 (5)
C140.04532 (13)0.18678 (16)0.61391 (16)0.0556 (4)
C150.10336 (15)0.12749 (16)0.5377 (2)0.0649 (5)
C160.16365 (15)0.18427 (15)0.46089 (19)0.0613 (5)
C170.02015 (19)0.1237 (3)0.6978 (2)0.0743 (6)
C210.5326 (2)0.5364 (2)0.1819 (2)0.0735 (6)
C220.57458 (18)0.6783 (3)0.3488 (2)0.0780 (7)
C610.3017 (2)0.6350 (2)0.02434 (17)0.0680 (5)
C620.25774 (18)0.81659 (18)0.1280 (2)0.0683 (5)
H40.3095 (14)0.4647 (14)0.2192 (15)0.051 (4)*
H70.2627 (17)0.3144 (19)0.317 (2)0.080 (6)*
H120.1111 (18)0.445 (2)0.534 (2)0.082 (7)*
H130.010 (2)0.349 (2)0.664 (2)0.091 (7)*
H150.1021 (18)0.045 (2)0.541 (2)0.084 (7)*
H160.2028 (18)0.1411 (19)0.408 (2)0.077 (6)*
H210.471 (2)0.486 (3)0.128 (3)0.115 (9)*
H220.577 (2)0.487 (2)0.224 (3)0.114 (10)*
H230.5712 (19)0.578 (2)0.128 (2)0.090 (7)*
H240.544 (2)0.735 (2)0.403 (2)0.094 (8)*
H250.617 (2)0.622 (2)0.398 (3)0.103 (8)*
H260.622 (2)0.720 (2)0.301 (2)0.102 (8)*
H310.3992 (13)0.6047 (15)0.4166 (16)0.049 (4)*
H320.4529 (16)0.4872 (18)0.3789 (19)0.069 (6)*
H510.1756 (16)0.6090 (16)0.1907 (17)0.059 (5)*
H520.2365 (14)0.6795 (15)0.3034 (16)0.054 (5)*
H610.3255 (17)0.554 (2)0.032 (2)0.078 (6)*
H620.229 (2)0.642 (2)0.018 (2)0.097 (8)*
H630.3492 (18)0.6748 (18)0.028 (2)0.075 (6)*
H640.181 (2)0.807 (2)0.089 (2)0.090 (7)*
H650.293 (2)0.859 (2)0.068 (2)0.094 (7)*
H660.2626 (19)0.860 (2)0.207 (2)0.089 (7)*
H710.012 (3)0.162 (4)0.774 (4)0.179 (17)*
H720.087 (3)0.119 (3)0.671 (3)0.139 (12)*
H730.019 (3)0.060 (3)0.737 (3)0.143 (12)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0651 (8)0.0581 (7)0.0788 (8)0.0142 (6)0.0211 (6)0.0164 (6)
N10.0498 (7)0.0426 (7)0.0526 (7)0.0055 (5)0.0150 (6)0.0038 (5)
N20.0627 (8)0.0455 (7)0.0573 (8)0.0085 (6)0.0226 (6)0.0003 (6)
C20.0455 (8)0.0550 (9)0.0540 (9)0.0013 (7)0.0128 (7)0.0074 (7)
C30.0528 (9)0.0478 (8)0.0518 (9)0.0031 (7)0.0149 (7)0.0075 (7)
C40.0576 (9)0.0409 (8)0.0524 (8)0.0057 (7)0.0200 (7)0.0009 (6)
C50.0463 (8)0.0515 (9)0.0542 (9)0.0054 (7)0.0105 (7)0.0028 (7)
C60.0488 (8)0.0494 (9)0.0508 (8)0.0031 (7)0.0098 (7)0.0043 (7)
C70.0513 (9)0.0454 (8)0.0545 (9)0.0020 (6)0.0154 (7)0.0017 (7)
C110.0464 (8)0.0456 (8)0.0549 (9)0.0022 (6)0.0098 (7)0.0057 (6)
C120.0733 (12)0.0484 (9)0.0710 (11)0.0039 (8)0.0282 (9)0.0017 (8)
C130.0720 (12)0.0657 (12)0.0686 (11)0.0040 (9)0.0308 (9)0.0030 (9)
C140.0408 (8)0.0664 (10)0.0598 (9)0.0040 (7)0.0069 (7)0.0149 (8)
C150.0616 (11)0.0475 (9)0.0892 (13)0.0018 (8)0.0241 (10)0.0178 (9)
C160.0628 (10)0.0469 (9)0.0794 (12)0.0039 (8)0.0290 (9)0.0074 (8)
C170.0519 (11)0.0990 (17)0.0737 (13)0.0116 (11)0.0144 (10)0.0272 (12)
C210.0776 (14)0.0710 (13)0.0795 (13)0.0230 (11)0.0400 (12)0.0139 (11)
C220.0542 (11)0.1041 (18)0.0744 (13)0.0186 (12)0.0020 (10)0.0171 (13)
C610.0762 (13)0.0766 (14)0.0513 (10)0.0143 (11)0.0082 (9)0.0009 (9)
C620.0646 (12)0.0615 (12)0.0812 (14)0.0095 (9)0.0190 (10)0.0223 (10)
Geometric parameters (Å, º) top
O1—N11.2846 (16)C12—H120.94 (2)
N1—C21.494 (2)C13—C141.386 (3)
N1—C61.488 (2)C13—H130.95 (3)
N2—C41.4690 (19)C14—C151.376 (3)
N2—C71.251 (2)C14—C171.514 (2)
C2—C221.517 (3)C15—C161.383 (3)
C2—C31.531 (2)C15—H150.96 (2)
C2—C211.541 (3)C16—H160.96 (2)
C3—C41.513 (2)C17—H710.97 (5)
C3—H311.006 (18)C17—H720.85 (3)
C3—H320.98 (2)C17—H730.96 (4)
C4—C51.517 (2)C21—H211.09 (3)
C4—H40.984 (17)C21—H220.89 (3)
C5—C61.531 (2)C21—H230.95 (3)
C5—H510.973 (19)C22—H241.00 (3)
C5—H521.014 (18)C22—H250.97 (3)
C6—C611.525 (3)C22—H260.98 (3)
C6—C621.531 (3)C61—H610.98 (2)
C7—C111.474 (2)C61—H620.97 (3)
C7—H70.99 (2)C61—H631.00 (2)
C11—C121.387 (2)C62—H641.01 (3)
C11—C161.387 (2)C62—H650.99 (3)
C12—C131.382 (3)C62—H661.02 (3)
O1···O1i5.688 (3)O1···H32ii2.56 (2)
O1···O1ii6.283 (2)O1···H22ii2.94 (3)
O1···O1iii6.069 (3)O1···H24iv2.94 (3)
O1···C3ii3.455 (2)O1···H31iv2.926 (18)
O1···C21ii3.567 (3)
O1—N1—C6115.66 (13)C12—C13—C14121.46 (18)
O1—N1—C2115.80 (12)C12—C13—H13119.3 (15)
C6—N1—C2123.89 (12)C14—C13—H13119.2 (15)
C7—N2—C4118.09 (14)C15—C14—C13117.63 (16)
N1—C2—C22107.91 (16)C15—C14—C17121.11 (19)
N1—C2—C3110.12 (12)C13—C14—C17121.26 (19)
C22—C2—C3108.79 (15)C14—C15—C16121.58 (18)
N1—C2—C21108.23 (15)C14—C15—H15117.4 (14)
C22—C2—C21110.08 (18)C16—C15—H15121.0 (14)
C3—C2—C21111.63 (16)C15—C16—C11120.63 (17)
C4—C3—C2114.62 (14)C15—C16—H16120.1 (13)
C4—C3—H31107.2 (10)C11—C16—H16119.2 (13)
C2—C3—H31109.7 (10)C14—C17—H71110 (3)
C4—C3—H32111.0 (12)C14—C17—H72113 (2)
C2—C3—H32106.7 (12)H71—C17—H72110 (3)
H31—C3—H32107.4 (15)C14—C17—H73112.4 (19)
N2—C4—C3109.13 (13)H71—C17—H7387 (3)
N2—C4—C5107.89 (13)H72—C17—H73122 (3)
C3—C4—C5108.43 (13)C2—C21—H21112.8 (15)
N2—C4—H4109.5 (10)C2—C21—H22109.1 (18)
C3—C4—H4111.8 (10)H21—C21—H22107 (2)
C5—C4—H4110.0 (10)C2—C21—H23110.9 (15)
C4—C5—C6114.77 (13)H21—C21—H23107 (2)
C4—C5—H51110.3 (11)H22—C21—H23109 (2)
C6—C5—H51107.0 (11)C2—C22—H24110.7 (15)
C4—C5—H52106.2 (10)C2—C22—H25110.4 (16)
C6—C5—H52109.2 (10)H24—C22—H25109 (2)
H51—C5—H52109.3 (15)C2—C22—H26110.7 (16)
N1—C6—C61109.17 (15)H24—C22—H26108 (2)
N1—C6—C5109.21 (13)H25—C22—H26108 (2)
C61—C6—C5111.96 (15)C6—C61—H61112.8 (13)
N1—C6—C62107.42 (14)C6—C61—H62109.1 (15)
C61—C6—C62109.95 (17)H61—C61—H62111.6 (19)
C5—C6—C62109.03 (14)C6—C61—H63110.6 (12)
N2—C7—C11122.60 (15)H61—C61—H63107.1 (17)
N2—C7—H7120.1 (13)H62—C61—H63105.4 (19)
C11—C7—H7117.0 (13)C6—C62—H64107.0 (13)
C12—C11—C16118.13 (15)C6—C62—H65109.3 (14)
C12—C11—C7121.89 (15)H64—C62—H65104.2 (19)
C16—C11—C7119.97 (15)C6—C62—H66111.4 (13)
C13—C12—C11120.57 (18)H64—C62—H66112.5 (19)
C13—C12—H12120.9 (14)H65—C62—H66112.0 (19)
C11—C12—H12118.5 (14)
O1—N1—C2—C3168.74 (13)C2—N1—C6—C6185.36 (18)
O1—N1—C6—C5167.92 (13)O1—N1—C6—C6249.80 (19)
C6—N1—C2—C336.5 (2)C2—N1—C6—C62155.45 (15)
C2—N1—C6—C537.34 (19)C4—C5—C6—C6173.8 (2)
N1—C2—C3—C445.18 (19)C4—C5—C6—C62164.33 (16)
C4—C5—C6—N147.24 (19)C4—N2—C7—C11179.61 (14)
C2—C3—C4—C557.23 (18)N2—C7—C11—C121.3 (3)
C3—C4—C5—C658.65 (18)N2—C7—C11—C16179.85 (18)
C2—C3—C4—N2174.51 (13)C16—C11—C12—C130.2 (3)
N2—C4—C5—C6176.72 (13)C7—C11—C12—C13178.60 (17)
C7—N2—C4—C3100.27 (18)C11—C12—C13—C140.6 (3)
C7—N2—C4—C5142.12 (16)C12—C13—C14—C150.4 (3)
O1—N1—C2—C2250.1 (2)C12—C13—C14—C17179.3 (2)
C6—N1—C2—C22155.16 (16)C13—C14—C15—C160.1 (3)
O1—N1—C2—C2168.98 (19)C17—C14—C15—C16179.8 (2)
C6—N1—C2—C2185.74 (19)C14—C15—C16—C110.5 (3)
C22—C2—C3—C4163.26 (18)C12—C11—C16—C150.3 (3)
C21—C2—C3—C475.1 (2)C7—C11—C16—C15179.18 (17)
O1—N1—C6—C6169.38 (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, z1/2.
(11b) 4-(4-methylphenylmethyleneamino)-2,2,6,6-tetramethylpiperidin-1-oxyl top
Crystal data top
C17H25N2OF(000) = 596.00
Mr = 273.40Dx = 1.154 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
a = 12.4422 (19) ÅCell parameters from 24 reflections
b = 11.495 (3) Åθ = 12.6–15.0°
c = 11.094 (2) ŵ = 0.07 mm1
β = 97.381 (13)°T = 100 K
V = 1573.6 (5) Å3Plate, orange
Z = 40.40 × 0.40 × 0.10 mm
Data collection top
Rigaku AFC7R
diffractometer
Rint = 0.017
Radiation source: Rigaku rotating anodeθmax = 27.5°, θmin = 2.4°
Graphite monochromatorh = 1616
ω–2θ scansk = 140
3796 measured reflectionsl = 014
3611 independent reflections3 standard reflections every 150 reflections
2992 reflections with I > 2σ(I) intensity decay: 0.6%
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: difmap and geom
R[F2 > 2σ(F2)] = 0.055All H-atom parameters refined
wR(F2) = 0.165Calculated w = 1/[σ2(Fo2) + (0.0592P)2 + 1.6154P]
where P = (Fo2 + 2Fc2)/3
S = 1.13(Δ/σ)max = 0.007
3611 reflectionsΔρmax = 0.47 e Å3
282 parametersΔρmin = 0.31 e Å3
0 restraintsExtinction correction: SHELXL-97 (Sheldrick, 1997), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.007 (2)
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
xyzUiso*/Ueq
O10.47708 (11)0.78360 (12)0.14217 (12)0.0255 (3)
N10.42109 (12)0.71120 (13)0.19716 (13)0.0186 (3)
N20.23560 (13)0.46947 (14)0.37086 (14)0.0220 (4)
C20.48362 (14)0.61719 (16)0.26835 (16)0.0204 (4)
C30.41180 (15)0.55299 (16)0.34805 (16)0.0199 (4)
C40.30014 (15)0.52007 (16)0.28271 (16)0.0204 (4)
C50.24364 (15)0.63096 (16)0.23265 (16)0.0206 (4)
C60.30457 (15)0.69875 (16)0.14455 (16)0.0199 (4)
C70.22959 (15)0.35961 (17)0.37574 (16)0.0212 (4)
C110.16685 (14)0.29946 (16)0.46046 (16)0.0200 (4)
C120.10796 (16)0.35985 (18)0.53973 (18)0.0248 (4)
C130.04808 (17)0.30089 (19)0.61674 (18)0.0272 (4)
C140.04456 (14)0.17910 (18)0.61830 (17)0.0233 (4)
C150.10319 (16)0.11921 (17)0.53939 (19)0.0252 (4)
C160.16343 (16)0.17822 (18)0.46109 (19)0.0251 (4)
C170.01952 (17)0.1150 (2)0.7033 (2)0.0291 (5)
C210.53044 (17)0.53498 (19)0.17904 (19)0.0270 (4)
C220.57665 (17)0.6747 (2)0.35070 (19)0.0289 (5)
C610.29865 (17)0.63899 (19)0.01955 (17)0.0256 (4)
C620.25623 (17)0.82115 (18)0.12750 (19)0.0266 (4)
H40.3066 (18)0.463 (2)0.215 (2)0.023 (5)*
H70.267 (2)0.306 (2)0.321 (2)0.040 (7)*
H120.110 (2)0.444 (2)0.537 (2)0.034 (7)*
H130.003 (2)0.346 (3)0.670 (3)0.054 (8)*
H150.100 (2)0.034 (2)0.540 (2)0.038 (7)*
H160.207 (2)0.133 (2)0.405 (3)0.043 (7)*
H210.473 (2)0.488 (2)0.128 (2)0.035 (7)*
H220.578 (2)0.480 (3)0.226 (3)0.045 (8)*
H230.573 (2)0.580 (2)0.125 (3)0.042 (7)*
H240.5499 (19)0.732 (2)0.405 (2)0.029 (6)*
H250.6158 (19)0.614 (2)0.400 (2)0.028 (6)*
H260.628 (2)0.720 (2)0.302 (3)0.043 (7)*
H310.4001 (19)0.601 (2)0.419 (2)0.031 (6)*
H320.4475 (18)0.483 (2)0.379 (2)0.020 (5)*
H510.1723 (18)0.6128 (19)0.1907 (19)0.018 (5)*
H520.236 (2)0.683 (2)0.302 (2)0.033 (6)*
H610.3154 (17)0.558 (2)0.0284 (19)0.016 (5)*
H620.225 (2)0.645 (2)0.022 (2)0.031 (6)*
H630.350 (2)0.680 (2)0.030 (2)0.035 (7)*
H640.181 (2)0.812 (2)0.091 (2)0.032 (6)*
H650.292 (2)0.868 (2)0.069 (3)0.044 (7)*
H660.263 (2)0.859 (2)0.208 (2)0.033 (6)*
H710.042 (4)0.165 (4)0.761 (4)0.110 (16)*
H720.081 (3)0.080 (4)0.665 (4)0.091 (13)*
H730.021 (3)0.058 (3)0.754 (3)0.069 (10)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0270 (7)0.0240 (7)0.0262 (7)0.0067 (5)0.0065 (5)0.0051 (5)
N10.0213 (7)0.0175 (7)0.0174 (7)0.0041 (6)0.0034 (6)0.0020 (6)
N20.0244 (8)0.0231 (8)0.0186 (7)0.0039 (6)0.0037 (6)0.0007 (6)
C20.0205 (9)0.0231 (9)0.0172 (8)0.0003 (7)0.0007 (6)0.0022 (7)
C30.0230 (9)0.0203 (9)0.0162 (8)0.0010 (7)0.0021 (7)0.0020 (7)
C40.0262 (9)0.0185 (9)0.0164 (8)0.0039 (7)0.0031 (7)0.0007 (7)
C50.0212 (9)0.0216 (9)0.0183 (8)0.0035 (7)0.0002 (7)0.0008 (7)
C60.0224 (9)0.0201 (9)0.0166 (8)0.0009 (7)0.0000 (7)0.0012 (6)
C70.0217 (9)0.0229 (9)0.0188 (8)0.0005 (7)0.0016 (7)0.0016 (7)
C110.0180 (8)0.0229 (9)0.0187 (8)0.0010 (7)0.0007 (6)0.0024 (7)
C120.0280 (10)0.0215 (9)0.0260 (9)0.0028 (7)0.0079 (7)0.0017 (7)
C130.0280 (10)0.0305 (11)0.0241 (9)0.0024 (8)0.0073 (8)0.0002 (8)
C140.0172 (8)0.0310 (10)0.0212 (9)0.0001 (7)0.0000 (7)0.0065 (7)
C150.0228 (9)0.0207 (9)0.0334 (10)0.0025 (7)0.0080 (8)0.0077 (8)
C160.0234 (9)0.0241 (10)0.0289 (10)0.0021 (7)0.0078 (7)0.0049 (8)
C170.0238 (10)0.0378 (12)0.0259 (10)0.0020 (9)0.0037 (8)0.0100 (9)
C210.0281 (10)0.0299 (10)0.0245 (9)0.0083 (8)0.0095 (8)0.0033 (8)
C220.0239 (10)0.0393 (12)0.0222 (9)0.0064 (9)0.0016 (8)0.0040 (9)
C610.0310 (10)0.0280 (10)0.0167 (9)0.0045 (8)0.0013 (7)0.0003 (7)
C620.0281 (10)0.0258 (10)0.0261 (10)0.0039 (8)0.0036 (8)0.0057 (8)
Geometric parameters (Å, º) top
O1—N11.2881 (19)C12—H120.97 (3)
N1—C21.496 (2)C13—C141.401 (3)
N1—C61.498 (2)C13—H131.00 (3)
N2—C41.463 (2)C14—C151.392 (3)
N2—C71.267 (3)C14—C171.504 (3)
C2—C31.526 (2)C15—C161.394 (3)
C2—C221.530 (3)C15—H150.98 (3)
C2—C211.537 (3)C16—H161.02 (3)
C3—C41.530 (3)C17—H710.93 (5)
C3—H310.99 (3)C17—H720.91 (4)
C3—H320.96 (2)C17—H730.96 (4)
C4—C51.526 (3)C21—H211.01 (3)
C4—H41.01 (2)C21—H220.97 (3)
C5—C61.526 (2)C21—H231.00 (3)
C5—H510.97 (2)C22—H240.98 (3)
C5—H520.99 (3)C22—H250.98 (3)
C6—C621.532 (3)C22—H261.03 (3)
C6—C611.541 (3)C61—H610.95 (2)
C7—C111.469 (2)C61—H620.98 (3)
C7—H71.02 (3)C61—H631.01 (3)
C11—C161.394 (3)C62—H640.98 (3)
C11—C121.399 (3)C62—H651.00 (3)
C12—C131.381 (3)C62—H660.99 (3)
O1···O1i5.6006 (11)O1···H32ii2.50 (2)
O1···O1ii6.2237 (17)O1···H22ii2.82 (3)
O1···O1iii5.958 (3)O1···H24iv2.89 (2)
O1···C3ii3.387 (3)O1···H31iv2.86 (3)
O1···C21ii3.513 (3)
O1—N1—C2116.13 (14)C12—C13—C14121.21 (19)
O1—N1—C6115.62 (14)C12—C13—H13119.6 (18)
C2—N1—C6123.23 (14)C14—C13—H13119.1 (18)
C7—N2—C4117.73 (16)C15—C14—C13117.83 (18)
N1—C2—C3110.59 (14)C15—C14—C17121.01 (19)
N1—C2—C22107.78 (16)C13—C14—C17121.15 (19)
C3—C2—C22108.52 (15)C14—C15—C16121.23 (18)
N1—C2—C21108.55 (14)C14—C15—H15118.0 (15)
C3—C2—C21112.01 (16)C16—C15—H15120.8 (15)
C22—C2—C21109.30 (16)C15—C16—C11120.57 (18)
C2—C3—C4114.14 (14)C15—C16—H16119.9 (16)
C2—C3—H31110.2 (14)C11—C16—H16119.5 (16)
C4—C3—H31107.4 (14)C14—C17—H71111 (3)
C2—C3—H32109.6 (13)C14—C17—H72114 (3)
C4—C3—H32108.3 (13)H71—C17—H72106 (4)
H31—C3—H32106.9 (19)C14—C17—H73115 (2)
N2—C4—C5107.98 (15)H71—C17—H73102 (3)
N2—C4—C3108.94 (14)H72—C17—H73108 (3)
C5—C4—C3108.29 (15)C2—C21—H21113.2 (15)
N2—C4—H4109.7 (13)C2—C21—H22107.9 (17)
C5—C4—H4110.7 (13)H21—C21—H22107 (2)
C3—C4—H4111.1 (13)C2—C21—H23110.4 (16)
C4—C5—C6114.61 (15)H21—C21—H23109 (2)
C4—C5—H51110.2 (13)H22—C21—H23109 (2)
C6—C5—H51107.6 (13)C2—C22—H24111.6 (14)
C4—C5—H52107.8 (15)C2—C22—H25107.9 (14)
C6—C5—H52107.4 (14)H24—C22—H25109 (2)
H51—C5—H52109.2 (19)C2—C22—H26112.3 (16)
N1—C6—C5109.56 (14)H24—C22—H26105 (2)
N1—C6—C62107.77 (15)H25—C22—H26111 (2)
C5—C6—C62109.19 (16)C6—C61—H61110.9 (13)
N1—C6—C61108.97 (15)C6—C61—H62108.9 (14)
C5—C6—C61112.25 (16)H61—C61—H62107.0 (19)
C62—C6—C61109.00 (16)C6—C61—H63108.8 (15)
N2—C7—C11122.38 (18)H61—C61—H63111.7 (19)
N2—C7—H7122.7 (15)H62—C61—H63109 (2)
C11—C7—H7114.9 (15)C6—C62—H64107.1 (15)
C16—C11—C12118.29 (17)C6—C62—H65112.1 (16)
C16—C11—C7119.51 (17)H64—C62—H65106 (2)
C12—C11—C7122.18 (17)C6—C62—H66107.8 (15)
C13—C12—C11120.86 (19)H64—C62—H66113 (2)
C13—C12—H12121.9 (15)H65—C62—H66111 (2)
C11—C12—H12117.2 (15)
O1—N1—C2—C3168.89 (14)C2—N1—C6—C62156.46 (16)
O1—N1—C6—C5168.33 (15)O1—N1—C6—C6168.50 (19)
C6—N1—C2—C337.3 (2)C2—N1—C6—C6185.39 (19)
C2—N1—C6—C537.8 (2)C4—C5—C6—C62165.30 (16)
N1—C2—C3—C445.9 (2)C4—C5—C6—C6173.7 (2)
C4—C5—C6—N147.5 (2)C4—N2—C7—C11179.81 (15)
C2—C3—C4—C557.4 (2)N2—C7—C11—C16179.90 (18)
C3—C4—C5—C658.64 (19)N2—C7—C11—C121.2 (3)
C2—C3—C4—N2174.61 (15)C16—C11—C12—C130.1 (3)
N2—C4—C5—C6176.46 (14)C7—C11—C12—C13178.76 (18)
C7—N2—C4—C398.95 (19)C11—C12—C13—C140.2 (3)
C7—N2—C4—C5143.65 (17)C12—C13—C14—C150.2 (3)
O1—N1—C2—C2250.4 (2)C12—C13—C14—C17179.21 (19)
C6—N1—C2—C22155.80 (16)C13—C14—C15—C160.1 (3)
O1—N1—C2—C2167.8 (2)C17—C14—C15—C16179.48 (19)
C6—N1—C2—C2185.93 (19)C14—C15—C16—C110.3 (3)
C22—C2—C3—C4163.94 (17)C12—C11—C16—C150.3 (3)
C21—C2—C3—C475.3 (2)C7—C11—C16—C15179.06 (17)
O1—N1—C6—C6249.6 (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, z1/2.
(12) 4-(2-naphthylmethyleneamino)-2,2,6,6-tetramethylpiperidin-1-oxyl top
Crystal data top
C20H25N2ODx = 1.189 Mg m3
Mr = 309.43Melting point: not measured K
Orthorhombic, Pna21Mo Kα radiation, λ = 0.71073 Å
a = 20.0837 (19) ÅCell parameters from 25 reflections
b = 5.6969 (7) Åθ = 13.6–17.2°
c = 15.106 (2) ŵ = 0.07 mm1
V = 1728.4 (4) Å3T = 295 K
Z = 4Prism, orange
F(000) = 668.000.50 × 0.38 × 0.10 mm
Data collection top
Rigaku AFC5R
diffractometer
Rint = 0.000
Radiation source: Rigaku rotating anodeθmax = 27.5°, θmin = 2.7°
Graphite monochromatorh = 026
ω–2θ scansk = 07
2059 measured reflectionsl = 019
2059 independent reflections3 standard reflections every 100 reflections
1491 reflections with I > 2σ(I) intensity decay: 0.2%
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: difmap and geom
R[F2 > 2σ(F2)] = 0.043H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.110Calculated w = 1/[σ2(Fo2) + (0.0544P)2 + 0.0293P]
where P = (Fo2 + 2Fc2)/3
S = 1.07(Δ/σ)max = 0.004
2059 reflectionsΔρmax = 0.16 e Å3
260 parametersΔρmin = 0.13 e Å3
0 restraintsExtinction correction: SHELXL-97 (Sheldrick, 1997), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.017 (2)
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
xyzUiso*/Ueq
O10.09774 (12)0.3230 (4)0.10120.0602 (7)
N10.05695 (12)0.1653 (4)0.0734 (2)0.0430 (6)
N20.07109 (12)0.3991 (4)0.0066 (2)0.0439 (6)
C20.01415 (14)0.0529 (5)0.1420 (3)0.0396 (7)
C30.04118 (15)0.0899 (6)0.0980 (3)0.0417 (7)
C40.01643 (15)0.2424 (5)0.0221 (3)0.0397 (7)
C50.01272 (18)0.0808 (6)0.0477 (3)0.0438 (7)
C60.07313 (14)0.0602 (5)0.0148 (3)0.0434 (7)
C70.09733 (15)0.3735 (6)0.0819 (3)0.0427 (7)
C110.14907 (14)0.5293 (5)0.1170 (3)0.0393 (7)
C120.17172 (15)0.4933 (6)0.2009 (3)0.0435 (7)
C130.21842 (14)0.6465 (6)0.2413 (3)0.0408 (7)
C140.24184 (14)0.8406 (6)0.1928 (3)0.0447 (7)
C150.21882 (17)0.8718 (7)0.1045 (3)0.0508 (8)
C160.17416 (16)0.7218 (6)0.0684 (3)0.0488 (8)
C170.24120 (17)0.6118 (8)0.3288 (3)0.0540 (9)
C180.28408 (17)0.7677 (8)0.3670 (3)0.0632 (11)
C190.30683 (18)0.9607 (8)0.3193 (3)0.0639 (11)
C200.28659 (18)0.9984 (8)0.2347 (3)0.0570 (9)
C210.01701 (17)0.2516 (6)0.1962 (3)0.0503 (8)
C220.05755 (17)0.1012 (6)0.2019 (3)0.0526 (8)
C610.13571 (16)0.0933 (6)0.0053 (3)0.0636 (10)
C620.0870 (2)0.2606 (6)0.0789 (3)0.0608 (10)
H40.0188 (14)0.356 (5)0.047 (2)0.039 (8)*
H70.0861 (16)0.249 (6)0.120 (2)0.045 (9)*
H120.1555 (14)0.370 (5)0.235 (2)0.036 (7)*
H150.2316 (15)1.005 (6)0.076 (2)0.045 (9)*
H160.1606 (18)0.749 (7)0.010 (3)0.073 (12)*
H170.2256 (17)0.481 (7)0.355 (3)0.063 (12)*
H180.2997 (19)0.736 (7)0.423 (3)0.068 (11)*
H190.3379 (19)1.062 (8)0.342 (3)0.072 (12)*
H200.2995 (19)1.127 (8)0.205 (3)0.070 (13)*
H210.03750.36170.15830.058*
H220.01770.32970.22910.058*
H230.04840.18980.23670.058*
H240.03220.15410.25170.063*
H250.07360.23310.17030.063*
H260.09470.01230.22340.063*
H310.0605 (17)0.194 (7)0.142 (3)0.060 (10)*
H320.0761 (15)0.011 (6)0.074 (2)0.048 (9)*
H510.0240 (15)0.027 (5)0.069 (2)0.037 (8)*
H520.0267 (15)0.156 (6)0.096 (2)0.047 (9)*
H610.14550.16440.06300.075*
H620.12750.21680.03480.075*
H630.17220.00340.01180.075*
H640.04950.36200.08180.070*
H650.12480.34630.05990.070*
H660.09540.19910.13690.070*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0635 (14)0.0501 (12)0.0670 (15)0.0179 (11)0.0085 (13)0.0168 (12)
N10.0454 (13)0.0367 (12)0.0468 (14)0.0043 (11)0.0053 (12)0.0046 (12)
N20.0455 (13)0.0456 (14)0.0406 (14)0.0090 (12)0.0042 (11)0.0042 (13)
C20.0445 (15)0.0384 (16)0.0358 (14)0.0011 (13)0.0037 (13)0.0029 (13)
C30.0384 (15)0.0467 (17)0.0398 (16)0.0026 (14)0.0009 (14)0.0000 (15)
C40.0411 (15)0.0425 (16)0.0354 (14)0.0056 (15)0.0035 (13)0.0059 (14)
C50.0501 (18)0.0455 (18)0.0358 (16)0.0069 (16)0.0020 (14)0.0071 (15)
C60.0402 (15)0.0422 (16)0.0478 (17)0.0073 (14)0.0042 (14)0.0101 (15)
C70.0439 (16)0.0445 (17)0.0397 (16)0.0056 (14)0.0010 (14)0.0021 (15)
C110.0373 (15)0.0423 (16)0.0382 (15)0.0008 (13)0.0013 (12)0.0052 (14)
C120.0414 (16)0.0470 (17)0.0421 (16)0.0087 (14)0.0004 (14)0.0021 (16)
C130.0334 (13)0.0463 (17)0.0427 (15)0.0008 (13)0.0004 (13)0.0095 (15)
C140.0352 (14)0.0495 (18)0.0492 (18)0.0030 (14)0.0011 (13)0.0064 (16)
C150.0499 (18)0.0488 (19)0.054 (2)0.0120 (16)0.0021 (16)0.0065 (17)
C160.0494 (18)0.055 (2)0.0419 (18)0.0033 (16)0.0064 (15)0.0034 (16)
C170.0469 (17)0.073 (2)0.0426 (17)0.0083 (18)0.0063 (15)0.0002 (19)
C180.0455 (18)0.097 (3)0.047 (2)0.008 (2)0.0092 (16)0.010 (2)
C190.0441 (18)0.081 (3)0.066 (3)0.0183 (19)0.0062 (18)0.024 (2)
C200.0495 (19)0.061 (2)0.060 (2)0.0123 (18)0.0004 (18)0.009 (2)
C210.062 (2)0.0465 (18)0.0423 (17)0.0064 (16)0.0030 (16)0.0103 (16)
C220.063 (2)0.0438 (18)0.0511 (18)0.0063 (16)0.0190 (16)0.0054 (16)
C610.0459 (17)0.059 (2)0.086 (3)0.0016 (17)0.0041 (19)0.015 (2)
C620.068 (2)0.055 (2)0.059 (2)0.0221 (18)0.0164 (18)0.0101 (19)
Geometric parameters (Å, º) top
O1—N11.286 (3)C13—C171.412 (5)
N1—C21.491 (4)C14—C201.421 (5)
N1—C61.497 (4)C14—C151.423 (5)
N2—C41.480 (4)C15—C161.353 (5)
N2—C71.262 (4)C15—H150.91 (3)
C2—C31.530 (4)C16—H160.93 (4)
C2—C211.531 (4)C17—C181.365 (5)
C2—C221.533 (4)C17—H170.90 (4)
C3—C41.521 (4)C18—C191.392 (6)
C3—H310.98 (4)C18—H180.92 (4)
C3—H320.98 (3)C19—C201.358 (6)
C4—C51.518 (4)C19—H190.91 (4)
C4—H41.03 (3)C20—H200.90 (4)
C5—C61.538 (4)C21—H210.944 (4)
C5—H511.01 (3)C21—H220.965 (4)
C5—H520.89 (4)C21—H230.946 (4)
C6—C621.523 (5)C22—H240.957 (4)
C6—C611.538 (4)C22—H250.947 (4)
C7—C111.466 (4)C22—H260.958 (3)
C7—H70.94 (3)C61—H610.982 (5)
C11—C121.362 (4)C61—H620.943 (4)
C11—C161.412 (4)C61—H630.930 (3)
C12—C131.419 (4)C62—H640.950 (4)
C12—H120.93 (3)C62—H650.948 (4)
C13—C141.407 (4)C62—H660.959 (4)
O1···O1i5.6969 (7)O1···C61i3.772 (5)
O1···O1ii8.748 (3)O1···H4i2.56 (3)
O1···C4i3.580 (4)O1···H25i2.78 (2)
O1···C12iii3.477 (4)O1···H62i2.87 (2)
O1···C17iii3.483 (4)O1···H12iii2.75 (3)
O1···C22i3.705 (4)O1···H17iii2.80 (4)
O1—N1—C2116.2 (2)C13—C14—C20118.5 (3)
O1—N1—C6115.6 (2)C13—C14—C15118.6 (3)
C2—N1—C6124.9 (2)C20—C14—C15123.0 (3)
C7—N2—C4120.3 (3)C16—C15—C14120.9 (3)
N1—C2—C3110.2 (2)C16—C15—H15121 (2)
N1—C2—C21106.8 (2)C14—C15—H15117 (2)
C3—C2—C21109.2 (2)C15—C16—C11121.2 (3)
N1—C2—C22109.2 (2)C15—C16—H16118 (2)
C3—C2—C22111.4 (3)C11—C16—H16121 (2)
C21—C2—C22109.9 (3)C18—C17—C13120.6 (4)
C4—C3—C2113.2 (2)C18—C17—H17125 (2)
C4—C3—H31107 (2)C13—C17—H17114 (2)
C2—C3—H31108 (2)C17—C18—C19120.2 (4)
C4—C3—H32107 (2)C17—C18—H18118 (3)
C2—C3—H32111.7 (18)C19—C18—H18121 (3)
H31—C3—H32109 (3)C20—C19—C18120.9 (4)
N2—C4—C5116.6 (2)C20—C19—H19117 (3)
N2—C4—C3108.8 (2)C18—C19—H19122 (3)
C5—C4—C3107.7 (2)C19—C20—C14120.6 (4)
N2—C4—H4103.9 (15)C19—C20—H20121 (3)
C5—C4—H4111.8 (16)C14—C20—H20118 (3)
C3—C4—H4107.7 (17)C2—C21—H21110.2 (3)
C4—C5—C6113.3 (3)C2—C21—H22108.8 (3)
C4—C5—H51108.1 (16)H21—C21—H22108.8 (3)
C6—C5—H51111.3 (16)C2—C21—H23110.0 (3)
C4—C5—H52114 (2)H21—C21—H23110.4 (3)
C6—C5—H52106 (2)H22—C21—H23108.6 (4)
H51—C5—H52105 (3)C2—C22—H24110.0 (3)
N1—C6—C62107.8 (2)C2—C22—H25110.5 (3)
N1—C6—C5109.0 (2)H24—C22—H25109.2 (4)
C62—C6—C5109.3 (3)C2—C22—H26109.9 (3)
N1—C6—C61108.7 (3)H24—C22—H26108.2 (4)
C62—C6—C61109.7 (3)H25—C22—H26109.0 (3)
C5—C6—C61112.2 (3)C6—C61—H61108.4 (4)
N2—C7—C11123.5 (3)C6—C61—H62109.9 (3)
N2—C7—H7122.7 (19)H61—C61—H62107.4 (3)
C11—C7—H7113.8 (19)C6—C61—H63110.9 (3)
C12—C11—C16118.8 (3)H61—C61—H63108.4 (4)
C12—C11—C7118.8 (3)H62—C61—H63111.8 (5)
C16—C11—C7122.4 (3)C6—C62—H64109.9 (3)
C11—C12—C13121.9 (3)C6—C62—H65109.8 (4)
C11—C12—H12120.7 (19)H64—C62—H65109.6 (4)
C13—C12—H12117.4 (19)C6—C62—H66109.8 (3)
C14—C13—C17119.3 (3)H64—C62—H66108.8 (5)
C14—C13—C12118.7 (3)H65—C62—H66108.9 (4)
C17—C13—C12122.1 (3)
O1—N1—C2—C3168.0 (2)C4—N2—C7—C11176.6 (3)
O1—N1—C6—C5167.4 (3)N2—C7—C11—C12176.7 (3)
C6—N1—C2—C333.8 (4)N2—C7—C11—C160.4 (5)
C2—N1—C6—C534.2 (4)C16—C11—C12—C131.5 (5)
N1—C2—C3—C445.7 (3)C7—C11—C12—C13175.7 (3)
C4—C5—C6—N147.2 (4)C11—C12—C13—C140.1 (4)
C2—C3—C4—C561.3 (3)C11—C12—C13—C17179.0 (3)
C3—C4—C5—C662.5 (4)C17—C13—C14—C201.5 (4)
C2—C3—C4—N2171.4 (3)C12—C13—C14—C20177.6 (3)
N2—C4—C5—C6174.9 (3)C17—C13—C14—C15179.5 (3)
C7—N2—C4—C3112.6 (3)C12—C13—C14—C151.4 (4)
C7—N2—C4—C59.4 (4)C13—C14—C15—C161.6 (5)
O1—N1—C2—C2149.5 (3)C20—C14—C15—C16177.4 (3)
C6—N1—C2—C21152.3 (3)C14—C15—C16—C110.2 (5)
O1—N1—C2—C2269.4 (3)C12—C11—C16—C151.4 (5)
C6—N1—C2—C2288.9 (3)C7—C11—C16—C15175.7 (3)
C21—C2—C3—C4162.7 (3)C14—C13—C17—C181.7 (5)
C22—C2—C3—C475.6 (3)C12—C13—C17—C18177.3 (3)
O1—N1—C6—C6248.9 (3)C13—C17—C18—C191.2 (6)
C2—N1—C6—C62152.8 (3)C17—C18—C19—C200.5 (6)
O1—N1—C6—C6170.0 (3)C18—C19—C20—C140.3 (6)
C2—N1—C6—C6188.4 (3)C13—C14—C20—C190.8 (5)
C4—C5—C6—C62164.8 (3)C15—C14—C20—C19179.8 (3)
C4—C5—C6—C6173.3 (4)
Symmetry codes: (i) x, y1, z; (ii) x, y1, z+1/2; (iii) x, y, z+1/2.
(13) 4-(4-phenoxyphenylmethyleneamino)-2,2,6,6-tetramethylpiperidin-1-oxyl top
Crystal data top
C22H27N2O2Dx = 1.157 Mg m3
Mr = 351.47Melting point: not measured K
Orthorhombic, Pca21Mo Kα radiation, λ = 0.71073 Å
a = 30.565 (9) ÅCell parameters from 25 reflections
b = 5.993 (2) Åθ = 14.2–17.2°
c = 22.032 (5) ŵ = 0.07 mm1
V = 4036 (2) Å3T = 297 K
Z = 8Needle, orange
F(000) = 1512.000.70 × 0.50 × 0.40 mm
Data collection top
Rigaku AFC4
diffractometer
Rint = 0.000
Radiation source: fine-focus sealed tubeθmax = 27.5°, θmin = 1.3°
Graphite monochromatorh = 039
ω–2θ scansk = 07
4763 measured reflectionsl = 280
4763 independent reflections3 standard reflections every 50 reflections
2517 reflections with I > 2σ(I) intensity decay: 0.0%
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.059Hydrogen site location: difmap and geom
wR(F2) = 0.124H atoms treated by a mixture of independent and constrained refinement
S = 0.97Calculated w = 1/[σ2(Fo2) + (0.0471P)2]
where P = (Fo2 + 2Fc2)/3
4763 reflections(Δ/σ)max = 0.001
468 parametersΔρmax = 0.16 e Å3
0 restraintsΔρmin = 0.16 e Å3
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
xyzUiso*/Ueq
O1A0.28562 (10)1.1004 (5)0.59080.0808 (10)
O2A0.50583 (10)0.1062 (5)0.25169 (18)0.0712 (9)
N1A0.30453 (10)0.9470 (5)0.56088 (19)0.0510 (9)
N2A0.37560 (12)0.5370 (5)0.4439 (2)0.0655 (10)
C2A0.34251 (12)0.8331 (7)0.5894 (2)0.0524 (10)
C3A0.37044 (12)0.7267 (6)0.5394 (2)0.0551 (11)
H31A0.39650.64640.55920.055*
H32A0.38520.85060.51650.055*
C4A0.34539 (13)0.5962 (6)0.4928 (2)0.0519 (11)
H4A0.33270.46380.50930.052*
C5A0.30986 (14)0.7386 (7)0.4647 (2)0.0582 (11)
H51A0.32390.85150.43890.058*
H52A0.29380.66550.43210.058*
C6A0.27820 (13)0.8489 (7)0.5096 (2)0.0548 (10)
C7A0.38865 (13)0.3412 (6)0.4382 (2)0.0516 (10)
H7A0.37940.23240.46600.052*
C11A0.42016 (12)0.2741 (6)0.3901 (2)0.0494 (10)
C12A0.43834 (13)0.0638 (6)0.3888 (2)0.0543 (11)
H12A0.42990.03270.41770.054*
C13A0.46770 (13)0.0002 (6)0.3445 (2)0.0544 (11)
H13A0.48160.18490.34460.054*
C14A0.47874 (13)0.1514 (7)0.2991 (2)0.0536 (11)
C15A0.45981 (16)0.3623 (7)0.2987 (2)0.0658 (13)
H15A0.46770.45550.26540.066*
C16A0.43064 (14)0.4204 (7)0.3432 (3)0.0622 (12)
H16A0.41790.54900.34000.062*
C21A0.36960 (16)1.0082 (8)0.6232 (3)0.0820 (15)
H21A0.40140.94070.63950.082*
H22A0.37881.10950.59460.082*
H23A0.35491.06580.65340.082*
C22A0.32611 (15)0.6592 (8)0.6341 (2)0.0710 (13)
H24A0.35140.60230.65440.071*
H25A0.31090.51630.61700.071*
H26A0.30320.72680.65930.071*
C41A0.53273 (13)0.0840 (6)0.2540 (2)0.0523 (10)
C42A0.56344 (16)0.1073 (9)0.2976 (2)0.0720 (14)
H42A0.56270.02290.33110.072*
C43A0.58994 (16)0.2887 (11)0.2969 (3)0.0891 (17)
H43A0.60800.29850.32740.089*
C44A0.58517 (19)0.4503 (9)0.2532 (3)0.0910 (18)
H44A0.60210.57390.25380.091*
C45A0.55483 (19)0.4210 (8)0.2084 (3)0.0795 (15)
H45A0.55200.53600.17340.080*
C46A0.52761 (13)0.2394 (7)0.2090 (2)0.0588 (11)
H46A0.50760.20770.18370.059*
C61A0.24522 (14)0.6816 (8)0.5353 (2)0.0716 (13)
H61A0.22500.74360.57360.072*
H62A0.25860.55570.55910.072*
H63A0.22480.63750.50700.072*
C62A0.25424 (16)1.0416 (7)0.4783 (3)0.0785 (14)
H64A0.27451.14520.46320.078*
H65A0.23710.97820.44650.078*
H66A0.22821.11520.50530.078*
O1B0.03803 (11)1.5295 (5)0.60404 (19)0.0901 (11)
O2B0.25303 (12)0.5180 (5)0.25981 (19)0.0829 (10)
N1B0.05678 (11)1.3859 (5)0.57138 (19)0.0536 (9)
N2B0.12416 (11)0.9660 (5)0.45141 (19)0.0550 (9)
C2B0.09636 (12)1.2726 (6)0.5976 (2)0.0516 (10)
C3B0.12246 (12)1.1666 (6)0.5453 (2)0.0509 (10)
H31B0.14661.07800.55730.051*
H32B0.13581.27880.52140.051*
C4B0.09527 (12)1.0281 (6)0.5015 (2)0.0514 (10)
H4B0.08300.88350.52950.051*
C5B0.05883 (14)1.1692 (7)0.4757 (2)0.0601 (11)
H51B0.07141.27650.45240.060*
H52B0.04001.07930.44340.060*
C6B0.02950 (12)1.2784 (7)0.5229 (2)0.0553 (11)
C7B0.13438 (12)0.7632 (6)0.4430 (2)0.0476 (10)
H7B0.12440.64590.46990.048*
C11B0.16404 (12)0.6912 (6)0.3941 (2)0.0474 (10)
C12B0.18171 (12)0.4781 (6)0.3942 (2)0.0496 (10)
H12B0.17040.35100.42780.050*
C13B0.21172 (13)0.4157 (6)0.3505 (2)0.0513 (10)
H13B0.22600.28530.35190.051*
C14B0.22453 (13)0.5648 (7)0.3063 (2)0.0546 (11)
C15B0.20540 (15)0.7761 (7)0.3049 (2)0.0658 (12)
H15B0.21270.86960.27290.066*
C16B0.17615 (13)0.8363 (6)0.3485 (2)0.0538 (11)
H16B0.15940.97760.34430.054*
C21B0.12413 (15)1.4547 (7)0.6274 (3)0.0751 (14)
H21B0.15111.41380.64240.075*
H22B0.13091.57440.60340.075*
H23B0.10071.54990.66350.075*
C22B0.08288 (16)1.1055 (8)0.6450 (3)0.0771 (14)
H24B0.10430.04310.66450.077*
H25B0.06630.97920.62750.077*
H26B0.05741.16520.67790.077*
C41B0.27666 (15)0.3195 (8)0.2584 (3)0.0633 (12)
C42B0.30733 (17)0.2689 (9)0.3023 (3)0.0814 (15)
H42B0.31050.38030.33080.081*
C43B0.33094 (16)0.0747 (10)0.2971 (3)0.0912 (17)
H43B0.35220.06440.32990.091*
C44B0.32445 (17)0.0652 (9)0.2499 (3)0.0828 (15)
H44B0.34120.22510.25080.083*
C45B0.29440 (18)0.0108 (9)0.2069 (3)0.0797 (15)
H45B0.29270.11250.17310.080*
C46B0.27032 (14)0.1813 (8)0.2110 (2)0.0674 (13)
H46B0.25160.21550.18400.067*
C61B0.00233 (14)1.1093 (8)0.5519 (3)0.0728 (14)
H61B0.01661.16650.59440.073*
H62B0.01210.95600.56230.073*
H63B0.02401.07130.52250.073*
C62B0.00396 (17)1.4662 (8)0.4919 (3)0.0848 (16)
H64B0.02091.58900.48430.085*
H65B0.01961.39540.46280.085*
H66B0.01521.52780.52010.085*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O1A0.080 (2)0.080 (2)0.083 (2)0.0257 (18)0.0040 (19)0.031 (2)
O2A0.088 (2)0.0659 (19)0.0599 (19)0.0224 (18)0.0213 (17)0.0049 (16)
N1A0.049 (2)0.053 (2)0.051 (2)0.0082 (17)0.0027 (16)0.0146 (17)
N2A0.079 (3)0.0443 (19)0.073 (3)0.0045 (19)0.028 (2)0.0060 (19)
C2A0.050 (2)0.059 (2)0.049 (2)0.002 (2)0.006 (2)0.011 (2)
C3A0.052 (2)0.057 (2)0.057 (3)0.006 (2)0.001 (2)0.007 (2)
C4A0.056 (3)0.045 (2)0.055 (3)0.002 (2)0.012 (2)0.006 (2)
C5A0.070 (3)0.059 (2)0.046 (2)0.001 (2)0.002 (2)0.008 (2)
C6A0.051 (2)0.055 (2)0.059 (3)0.004 (2)0.007 (2)0.010 (2)
C7A0.048 (2)0.046 (2)0.061 (3)0.0034 (19)0.006 (2)0.004 (2)
C11A0.048 (2)0.050 (2)0.050 (2)0.004 (2)0.003 (2)0.006 (2)
C12A0.055 (3)0.047 (2)0.061 (3)0.008 (2)0.005 (2)0.004 (2)
C13A0.053 (3)0.051 (2)0.060 (3)0.004 (2)0.009 (2)0.004 (2)
C14A0.058 (3)0.058 (3)0.045 (2)0.002 (2)0.010 (2)0.007 (2)
C15A0.084 (3)0.044 (2)0.069 (3)0.009 (2)0.026 (3)0.007 (2)
C16A0.065 (3)0.040 (2)0.081 (3)0.004 (2)0.010 (3)0.013 (2)
C21A0.075 (3)0.091 (4)0.080 (3)0.012 (3)0.017 (3)0.022 (3)
C22A0.082 (3)0.078 (3)0.053 (3)0.015 (3)0.001 (2)0.005 (3)
C41A0.050 (2)0.051 (2)0.056 (3)0.001 (2)0.014 (2)0.004 (2)
C42A0.074 (3)0.088 (4)0.054 (3)0.007 (3)0.008 (3)0.010 (3)
C43A0.065 (3)0.122 (5)0.081 (4)0.015 (4)0.011 (3)0.008 (4)
C44A0.087 (4)0.089 (4)0.096 (4)0.043 (3)0.027 (4)0.023 (4)
C45A0.104 (4)0.055 (3)0.079 (4)0.015 (3)0.028 (3)0.016 (3)
C46A0.065 (3)0.068 (3)0.043 (2)0.003 (3)0.005 (2)0.002 (2)
C61A0.050 (3)0.089 (3)0.076 (3)0.004 (3)0.007 (2)0.006 (3)
C62A0.071 (3)0.072 (3)0.093 (4)0.020 (3)0.026 (3)0.004 (3)
O1B0.088 (2)0.083 (2)0.100 (3)0.029 (2)0.007 (2)0.041 (2)
O2B0.108 (3)0.075 (2)0.065 (2)0.012 (2)0.0391 (19)0.0026 (18)
N1B0.056 (2)0.047 (2)0.058 (2)0.0107 (17)0.0012 (18)0.0071 (18)
N2B0.066 (2)0.0462 (19)0.052 (2)0.0005 (18)0.0119 (18)0.0026 (18)
C2B0.053 (2)0.048 (2)0.054 (2)0.000 (2)0.003 (2)0.004 (2)
C3B0.047 (2)0.049 (2)0.056 (3)0.005 (2)0.002 (2)0.007 (2)
C4B0.051 (2)0.047 (2)0.056 (2)0.003 (2)0.012 (2)0.003 (2)
C5B0.066 (3)0.057 (3)0.057 (3)0.007 (2)0.009 (2)0.004 (2)
C6B0.045 (2)0.053 (2)0.068 (3)0.002 (2)0.008 (2)0.010 (2)
C7B0.051 (2)0.043 (2)0.049 (2)0.009 (2)0.004 (2)0.003 (2)
C11B0.052 (2)0.045 (2)0.045 (2)0.0053 (19)0.000 (2)0.004 (2)
C12B0.050 (2)0.045 (2)0.055 (3)0.008 (2)0.009 (2)0.004 (2)
C13B0.058 (3)0.045 (2)0.051 (2)0.005 (2)0.001 (2)0.005 (2)
C14B0.062 (3)0.050 (3)0.052 (3)0.000 (2)0.006 (2)0.002 (2)
C15B0.086 (3)0.064 (3)0.048 (3)0.006 (3)0.014 (3)0.007 (2)
C16B0.065 (3)0.040 (2)0.056 (3)0.000 (2)0.005 (2)0.001 (2)
C21B0.069 (3)0.066 (3)0.090 (4)0.007 (3)0.023 (3)0.010 (3)
C22B0.088 (4)0.084 (3)0.059 (3)0.001 (3)0.006 (3)0.008 (3)
C41B0.062 (3)0.072 (3)0.056 (3)0.000 (3)0.014 (2)0.008 (3)
C42B0.082 (3)0.090 (4)0.072 (3)0.008 (3)0.002 (3)0.028 (3)
C43B0.057 (3)0.123 (5)0.093 (4)0.010 (3)0.010 (3)0.009 (4)
C44B0.068 (3)0.085 (4)0.096 (4)0.010 (3)0.017 (3)0.009 (4)
C45B0.091 (4)0.077 (4)0.071 (3)0.015 (3)0.024 (3)0.028 (3)
C46B0.064 (3)0.083 (3)0.055 (3)0.006 (3)0.004 (2)0.004 (3)
C61B0.051 (3)0.077 (3)0.090 (4)0.000 (3)0.001 (3)0.020 (3)
C62B0.077 (3)0.066 (3)0.112 (4)0.022 (3)0.033 (3)0.011 (3)
Geometric parameters (Å, º) top
O1A—N1A1.270 (4)O1B—N1B1.260 (4)
O2A—C14A1.361 (5)O2B—C14B1.374 (5)
O2A—C41A1.407 (5)O2B—C41B1.392 (5)
N1A—C2A1.486 (5)N1B—C2B1.502 (5)
N1A—C6A1.507 (5)N1B—C6B1.501 (5)
N2A—C4A1.464 (5)N2B—C4B1.462 (5)
N2A—C7A1.246 (5)N2B—C7B1.268 (4)
C2A—C3A1.531 (5)C2B—C22B1.505 (6)
C2A—C21A1.531 (6)C2B—C21B1.530 (5)
C2A—C22A1.520 (6)C2B—C3B1.538 (5)
C3A—C4A1.501 (5)C3B—C4B1.520 (5)
C4A—C5A1.513 (5)C4B—C5B1.510 (5)
C5A—C6A1.533 (6)C5B—C6B1.521 (6)
C6A—C61A1.531 (6)C6B—C62B1.531 (6)
C6A—C62A1.532 (6)C6B—C61B1.543 (6)
C7A—C11A1.488 (5)C7B—C11B1.473 (5)
C11A—C12A1.377 (5)C3B—H31B0.945 (4)
C11A—C16A1.392 (6)C3B—H32B0.947 (4)
C12A—C13A1.379 (5)C4B—H4B1.127 (4)
C13A—C14A1.391 (5)C5B—H51B0.907 (4)
C14A—C15A1.390 (5)C5B—H52B1.062 (5)
C15A—C16A1.371 (6)C7B—H7B0.968 (4)
C41A—C42A1.351 (6)C11B—C16B1.380 (5)
C41A—C46A1.369 (5)C11B—C12B1.386 (5)
C42A—C43A1.356 (7)C12B—C13B1.381 (5)
C43A—C44A1.374 (8)C13B—C14B1.379 (5)
C44A—C45A1.366 (8)C14B—C15B1.395 (6)
C45A—C46A1.370 (6)C15B—C16B1.360 (6)
C3A—H31A1.027 (4)C41B—C46B1.347 (6)
C3A—H32A1.005 (4)C41B—C42B1.380 (7)
C4A—H4A0.955 (4)C42B—C43B1.374 (7)
C5A—H51A0.982 (5)C43B—C44B1.350 (7)
C5A—H52A0.975 (5)C44B—C45B1.360 (7)
C7A—H7A0.938 (4)C45B—C46B1.369 (6)
C12A—H12A0.899 (5)C12B—H12B1.118 (4)
C13A—H13A1.187 (4)C13B—H13B0.895 (4)
C15A—H15A0.954 (5)C15B—H15B0.928 (5)
C16A—H16A0.866 (4)C16B—H16B0.994 (4)
C21A—H21A1.113 (5)C21B—H21B0.922 (5)
C21A—H22A0.919 (6)C21B—H22B0.915 (5)
C21A—H23A0.873 (5)C21B—H23B1.213 (5)
C22A—H24A0.957 (5)C22B—H24B0.868 (5)
C22A—H25A1.044 (5)C22B—H25B0.990 (5)
C22A—H26A0.981 (5)C22B—H26B1.122 (5)
C42A—H42A1.073 (5)C42B—H42B0.922 (5)
C43A—H43A0.871 (6)C43B—H43B0.973 (6)
C44A—H44A0.904 (5)C44B—H44B1.087 (5)
C45A—H45A1.038 (5)C45B—H45B0.964 (5)
C46A—H46A0.849 (4)C46B—H46B0.849 (5)
C61A—H61A1.109 (5)C61B—H61B1.089 (5)
C61A—H62A1.005 (5)C61B—H62B1.044 (5)
C61A—H63A0.921 (5)C61B—H63B0.953 (5)
C62A—H64A0.938 (5)C62B—H64B0.915 (5)
C62A—H65A0.955 (5)C62B—H65B1.053 (5)
C62A—H66A1.087 (5)C62B—H66B0.932 (6)
O1A···O1B7.998 (5)O1A···H25Ai2.67
O1A···O1Ai5.993 (2)O1B···H62Bi2.83
O1B···O1Bi5.993 (2)O1A···H46Biii2.45
O1A···O1Bii8.033 (5)O1B···H46Aiv2.74
O1A···C22Ai3.695 (6)O2A···C45Ai3.344 (6)
O1B···C61Bi3.862 (6)O2B···C45Bi3.307 (6)
O1A···C46Biii3.189 (5)O2B···C44Bi3.325 (6)
O1B···C46Aiv3.361 (5)
C14A—O2A—C41A119.3 (3)H65A—C62A—H66A99.2 (4)
O1A—N1A—C2A117.9 (3)C14B—O2B—C41B121.3 (3)
O1A—N1A—C6A115.4 (3)O1B—N1B—C6B116.6 (3)
C2A—N1A—C6A123.7 (3)O1B—N1B—C2B117.1 (3)
C7A—N2A—C4A120.2 (3)C6B—N1B—C2B121.8 (3)
N1A—C2A—C3A108.9 (3)C7B—N2B—C4B120.2 (3)
N1A—C2A—C22A109.3 (3)N1B—C2B—C22B110.3 (3)
N1A—C2A—C21A108.3 (3)N1B—C2B—C21B106.8 (3)
C21A—C2A—C3A109.5 (3)C22B—C2B—C21B109.2 (4)
C22A—C2A—C3A111.4 (3)N1B—C2B—C3B108.5 (3)
C22A—C2A—C21A109.4 (4)C22B—C2B—C3B112.8 (3)
C4A—C3A—C2A115.1 (3)C21B—C2B—C3B109.1 (3)
N2A—C4A—C3A108.0 (3)C4B—C3B—C2B114.6 (3)
N2A—C4A—C5A106.7 (3)N2B—C4B—C5B107.6 (3)
C3A—C4A—C5A110.6 (3)N2B—C4B—C3B106.8 (3)
C4A—C5A—C6A115.6 (3)C5B—C4B—C3B109.7 (3)
N1A—C6A—C5A108.3 (3)C4B—C5B—C6B114.7 (3)
N1A—C6A—C61A109.2 (3)N1B—C6B—C5B110.1 (3)
N1A—C6A—C62A107.4 (3)N1B—C6B—C62B106.6 (3)
C61A—C6A—C5A111.9 (3)C5B—C6B—C62B108.2 (4)
C62A—C6A—C5A109.7 (4)N1B—C6B—C61B109.7 (4)
C61A—C6A—C62A110.2 (3)C5B—C6B—C61B111.8 (3)
N2A—C7A—C11A122.2 (4)C62B—C6B—C61B110.3 (3)
C12A—C11A—C7A121.5 (4)N2B—C7B—C11B122.6 (3)
C16A—C11A—C7A120.5 (3)C16B—C11B—C12B118.5 (4)
C12A—C11A—C16A118.0 (4)C16B—C11B—C7B120.9 (3)
C11A—C12A—C13A122.0 (4)C12B—C11B—C7B120.5 (4)
C12A—C13A—C14A119.1 (4)C13B—C12B—C11B120.5 (4)
O2A—C14A—C13A124.8 (4)C14B—C13B—C12B120.4 (4)
O2A—C14A—C15A115.4 (4)O2B—C14B—C13B125.1 (4)
C15A—C14A—C13A119.7 (4)O2B—C14B—C15B115.8 (4)
C16A—C15A—C14A119.8 (4)C13B—C14B—C15B119.0 (4)
C15A—C16A—C11A121.3 (4)C16B—C15B—C14B120.0 (4)
C42A—C41A—O2A121.0 (4)C15B—C16B—C11B121.5 (4)
C46A—C41A—O2A117.3 (4)C46B—C41B—C42B120.4 (4)
C42A—C41A—C46A121.6 (4)C46B—C41B—O2B117.9 (5)
C41A—C42A—C43A119.3 (5)C42B—C41B—O2B121.7 (4)
C42A—C43A—C44A120.6 (5)C43B—C42B—C41B119.0 (5)
C45A—C44A—C43A119.3 (5)C44B—C43B—C42B120.9 (5)
C44A—C45A—C46A120.5 (5)C43B—C44B—C45B119.2 (5)
C41A—C46A—C45A118.6 (4)C44B—C45B—C46B121.2 (5)
C2A—C3A—H31A108.8 (4)C41B—C46B—C45B119.4 (5)
C2A—C3A—H32A107.7 (4)C4B—C3B—H31B107.2 (4)
C4A—C3A—H31A116.2 (4)C2B—C3B—H31B115.4 (4)
C4A—C3A—H32A105.6 (4)C4B—C3B—H32B105.7 (4)
H31A—C3A—H32A102.2 (3)C2B—C3B—H32B110.3 (4)
N2A—C4A—H4A109.6 (3)H31B—C3B—H32B102.5 (3)
C3A—C4A—H4A112.3 (4)N2B—C4B—H4B114.7 (3)
C5A—C4A—H4A109.4 (4)C5B—C4B—H4B113.0 (3)
C4A—C5A—H51A108.2 (4)C3B—C4B—H4B104.8 (3)
C4A—C5A—H52A114.2 (4)C4B—C5B—H51B107.4 (4)
C6A—C5A—H51A110.6 (4)C6B—C5B—H51B109.2 (4)
C6A—C5A—H52A110.6 (4)C4B—C5B—H52B111.6 (4)
H51A—C5A—H52A95.8 (4)C6B—C5B—H52B110.9 (4)
N2A—C7A—H7A119.5 (4)H51B—C5B—H52B102.2 (4)
C11A—C7A—H7A118.2 (4)N2B—C7B—H7B121.9 (4)
C11A—C12A—H12A117.3 (4)C11B—C7B—H7B115.3 (4)
C13A—C12A—H12A120.7 (4)C13B—C12B—H12B118.9 (4)
C12A—C13A—H13A119.3 (4)C11B—C12B—H12B120.5 (4)
C14A—C13A—H13A121.5 (4)C14B—C13B—H13B116.8 (4)
C14A—C15A—H15A115.6 (4)C12B—C13B—H13B122.5 (5)
C16A—C15A—H15A124.6 (4)C16B—C15B—H15B122.3 (5)
C11A—C16A—H16A121.2 (5)C14B—C15B—H15B117.6 (4)
C15A—C16A—H16A117.4 (5)C15B—C16B—H16B120.0 (5)
C2A—C21A—H21A112.4 (4)C11B—C16B—H16B117.7 (4)
C2A—C21A—H22A106.5 (4)C2B—C21B—H21B117.4 (4)
C2A—C21A—H23A111.3 (4)C2B—C21B—H22B116.0 (5)
H21A—C21A—H22A101.2 (4)H21B—C21B—H22B102.2 (4)
H21A—C21A—H23A110.4 (5)C2B—C21B—H23B106.8 (4)
H22A—C21A—H23A114.7 (5)H21B—C21B—H23B114.8 (5)
C2A—C22A—H24A106.3 (4)H22B—C21B—H23B98.2 (4)
C2A—C22A—H25A118.3 (4)C2B—C22B—H25B112.2 (4)
C2A—C22A—H26A108.6 (4)C2B—C22B—H26B115.2 (4)
H24A—C22A—H25A103.7 (4)H25B—C22B—H26B98.0 (4)
H24A—C22A—H26A117.5 (5)C43B—C42B—H42B127.9 (6)
H25A—C22A—H26A103.0 (4)C41B—C42B—H42B113.0 (6)
C41A—C42A—H42A113.5 (5)C44B—C43B—H43B129.1 (6)
C43A—C42A—H42A127.1 (5)C42B—C43B—H43B110.0 (6)
C42A—C43A—H43A115.1 (7)C43B—C44B—H44B117.7 (6)
C44A—C43A—H43A124.1 (7)C45B—C44B—H44B122.8 (6)
C43A—C44A—H44A120.3 (7)C44B—C45B—H45B115.0 (6)
C45A—C44A—H44A120.4 (7)C46B—C45B—H45B123.7 (6)
C44A—C45A—H45A120.6 (5)C41B—C46B—H46B119.4 (5)
C46A—C45A—H45A118.9 (6)C45B—C46B—H46B121.2 (6)
C41A—C46A—H46A113.9 (5)C6B—C61B—H61B113.7 (4)
C45A—C46A—H46A127.4 (5)C6B—C61B—H62B113.8 (4)
C6A—C61A—H61A115.4 (4)H61B—C61B—H62B104.9 (5)
C6A—C61A—H62A114.6 (4)C6B—C61B—H63B108.2 (4)
C6A—C61A—H63A112.5 (4)H61B—C61B—H63B112.4 (4)
H61A—C61A—H62A94.7 (4)H62B—C61B—H63B103.4 (4)
H61A—C61A—H63A103.6 (4)C6B—C62B—H64B112.6 (4)
H62A—C61A—H63A114.4 (5)C6B—C62B—H65B108.9 (4)
C6A—C62A—H64A110.0 (4)H64B—C62B—H65B127.0 (6)
C6A—C62A—H65A107.0 (4)C6B—C62B—H66B108.3 (5)
C6A—C62A—H66A114.2 (4)H64B—C62B—H66B99.1 (5)
H64A—C62A—H65A111.6 (6)H65B—C62B—H66B97.8 (4)
H64A—C62A—H66A114.2 (4)
O1A—N1A—C2A—C3A158.2 (3)O1B—N1B—C2B—C3B161.7 (3)
O1A—N1A—C6A—C5A158.7 (3)O1B—N1B—C6B—C5B162.0 (3)
C6A—N1A—C2A—C3A42.2 (5)C6B—N1B—C2B—C3B43.1 (5)
C2A—N1A—C6A—C5A41.3 (5)C2B—N1B—C6B—C5B42.6 (5)
N1A—C2A—C3A—C4A46.9 (5)N1B—C2B—C3B—C4B48.6 (4)
C4A—C5A—C6A—N1A44.9 (5)C4B—C5B—C6B—N1B47.0 (5)
C2A—C3A—C4A—C5A54.7 (5)C2B—C3B—C4B—C5B56.5 (4)
C3A—C4A—C5A—C6A54.0 (5)C3B—C4B—C5B—C6B55.3 (4)
C2A—C3A—C4A—N2A171.1 (3)C2B—C3B—C4B—N2B172.8 (3)
N2A—C4A—C5A—C6A171.2 (3)N2B—C4B—C5B—C6B171.1 (3)
C7A—N2A—C4A—C3A107.0 (5)C7B—N2B—C4B—C3B114.0 (4)
C7A—N2A—C4A—C5A134.1 (4)C7B—N2B—C4B—C5B128.3 (4)
O1A—N1A—C2A—C22A79.9 (4)O1B—N1B—C2B—C22B74.4 (4)
C6A—N1A—C2A—C22A79.7 (4)C6B—N1B—C2B—C22B80.9 (5)
O1A—N1A—C2A—C21A39.2 (5)O1B—N1B—C2B—C21B44.1 (5)
C6A—N1A—C2A—C21A161.2 (4)C6B—N1B—C2B—C21B160.6 (4)
C22A—C2A—C3A—C4A73.8 (4)C22B—C2B—C3B—C4B73.8 (4)
C21A—C2A—C3A—C4A165.1 (3)C21B—C2B—C3B—C4B164.7 (3)
O1A—N1A—C6A—C61A79.2 (4)O1B—N1B—C6B—C62B44.9 (5)
C2A—N1A—C6A—C61A80.8 (4)C2B—N1B—C6B—C62B159.7 (4)
O1A—N1A—C6A—C62A40.3 (5)O1B—N1B—C6B—C61B74.5 (4)
C2A—N1A—C6A—C62A159.6 (4)C2B—N1B—C6B—C61B80.9 (4)
C4A—C5A—C6A—C61A75.5 (4)C4B—C5B—C6B—C62B163.1 (4)
C4A—C5A—C6A—C62A161.9 (3)C4B—C5B—C6B—C61B75.3 (4)
C4A—N2A—C7A—C11A178.6 (4)C4B—N2B—C7B—C11B178.7 (3)
N2A—C7A—C11A—C12A172.1 (4)N2B—C7B—C11B—C16B11.5 (6)
N2A—C7A—C11A—C16A10.7 (7)N2B—C7B—C11B—C12B166.1 (4)
C16A—C11A—C12A—C13A3.0 (6)C16B—C11B—C12B—C13B1.9 (6)
C7A—C11A—C12A—C13A179.7 (4)C7B—C11B—C12B—C13B175.8 (4)
C11A—C12A—C13A—C14A1.2 (6)C11B—C12B—C13B—C14B0.1 (6)
C41A—O2A—C14A—C15A168.0 (4)C41B—O2B—C14B—C13B9.4 (7)
C41A—O2A—C14A—C13A15.2 (6)C41B—O2B—C14B—C15B175.2 (4)
C12A—C13A—C14A—O2A177.2 (4)C12B—C13B—C14B—O2B177.9 (4)
C12A—C13A—C14A—C15A0.6 (6)C12B—C13B—C14B—C15B2.6 (6)
O2A—C14A—C15A—C16A177.4 (4)O2B—C14B—C15B—C16B178.9 (4)
C13A—C14A—C15A—C16A0.4 (7)C13B—C14B—C15B—C16B3.2 (7)
C14A—C15A—C16A—C11A1.5 (8)C14B—C15B—C16B—C11B1.2 (7)
C12A—C11A—C16A—C15A3.2 (7)C12B—C11B—C16B—C15B1.3 (6)
C7A—C11A—C16A—C15A179.5 (4)C7B—C11B—C16B—C15B176.3 (4)
C14A—O2A—C41A—C42A61.6 (5)C14B—O2B—C41B—C46B119.3 (5)
C14A—O2A—C41A—C46A120.9 (4)C14B—O2B—C41B—C42B63.9 (6)
C46A—C41A—C42A—C43A0.1 (7)C46B—C41B—C42B—C43B0.6 (8)
O2A—C41A—C42A—C43A177.3 (4)O2B—C41B—C42B—C43B177.3 (4)
C41A—C42A—C43A—C44A1.3 (8)C41B—C42B—C43B—C44B0.0 (8)
C42A—C43A—C44A—C45A3.3 (9)C42B—C43B—C44B—C45B0.7 (8)
C43A—C44A—C45A—C46A3.9 (8)C43B—C44B—C45B—C46B0.9 (8)
C42A—C41A—C46A—C45A0.7 (7)C42B—C41B—C46B—C45B0.4 (7)
O2A—C41A—C46A—C45A176.8 (4)O2B—C41B—C46B—C45B177.2 (4)
C44A—C45A—C46A—C41A2.6 (7)C44B—C45B—C46B—C41B0.3 (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
C17H25N2O3SF(000) = 724.00
Mr = 337.46Dx = 1.230 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
a = 11.1835 (18) ÅCell parameters from 24 reflections
b = 15.487 (2) Åθ = 17.2–17.4°
c = 11.5660 (18) ŵ = 0.19 mm1
β = 114.539 (11)°T = 294 K
V = 1822.2 (5) Å3Prism, orange
Z = 40.40 × 0.40 × 0.25 mm
Data collection top
Rigaku AFC7R
diffractometer
3223 reflections with I > 2σ(I)
Radiation source: Rigaku rotating anodeRint = 0.011
Graphite monochromatorθmax = 27.5°, θmin = 2.0°
ω–2θ scansh = 014
Absorption correction: ψ scans(north,Phillips & Mathews,1968)k = 020
Tmin = 0.976, Tmax = 1.000l = 1513
4390 measured reflections3 standard reflections every 150 reflections
4184 independent reflections intensity decay: 2.1%
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.041Hydrogen site location: difmap and geom
wR(F2) = 0.124All H-atom parameters refined
S = 1.01Calculated w = 1/[σ2(Fo2) + (0.0591P)2 + 0.4517P]
where P = (Fo2 + 2Fc2)/3
4184 reflections(Δ/σ)max = 0.002
308 parametersΔρmax = 0.22 e Å3
0 restraintsΔρmin = 0.37 e Å3
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
xyzUiso*/Ueq
S10.67906 (4)0.23050 (3)0.32526 (4)0.04993 (14)
O10.32575 (13)0.17790 (10)0.14263 (17)0.0777 (5)
O20.79800 (13)0.19177 (11)0.41330 (16)0.0791 (5)
O30.66697 (16)0.24230 (11)0.19877 (14)0.0780 (5)
N10.21831 (13)0.13885 (9)0.16040 (14)0.0466 (3)
N20.13684 (14)0.01037 (10)0.22219 (15)0.0550 (4)
C20.20524 (16)0.04898 (11)0.21003 (16)0.0455 (4)
C30.08984 (17)0.00427 (11)0.1966 (2)0.0494 (4)
C40.03315 (16)0.05922 (11)0.24018 (18)0.0477 (4)
C50.00093 (18)0.13977 (12)0.1584 (2)0.0502 (4)
C60.10558 (15)0.19526 (10)0.17114 (15)0.0437 (3)
C70.23087 (16)0.01568 (11)0.32082 (18)0.0480 (4)
C110.34033 (15)0.06780 (10)0.31885 (16)0.0437 (3)
C120.34551 (16)0.09204 (12)0.20499 (17)0.0493 (4)
C130.44757 (16)0.14254 (12)0.20545 (17)0.0480 (4)
C140.54568 (14)0.16726 (10)0.32084 (15)0.0426 (3)
C150.54249 (17)0.14415 (12)0.43496 (17)0.0498 (4)
C160.43876 (17)0.09491 (12)0.43305 (17)0.0498 (4)
C170.6596 (4)0.32873 (17)0.3911 (4)0.0928 (10)
C210.1871 (3)0.05072 (16)0.3485 (2)0.0635 (5)
C220.3321 (2)0.00156 (16)0.1293 (3)0.0666 (5)
C610.0540 (2)0.24426 (14)0.2979 (2)0.0611 (5)
C620.1565 (2)0.26078 (14)0.0635 (2)0.0607 (5)
H40.0623 (18)0.0726 (12)0.3295 (18)0.046 (5)*
H70.232 (2)0.0055 (14)0.401 (2)0.067 (6)*
H120.274 (2)0.0727 (13)0.1256 (19)0.058 (5)*
H130.449 (2)0.1593 (14)0.129 (2)0.064 (6)*
H150.613 (2)0.1604 (14)0.5149 (19)0.064 (6)*
H160.4339 (19)0.0787 (12)0.5097 (19)0.055 (5)*
H210.251 (2)0.0867 (16)0.358 (2)0.085 (8)*
H220.102 (2)0.0751 (15)0.408 (2)0.070 (7)*
H230.195 (2)0.0086 (17)0.374 (2)0.083 (7)*
H240.324 (2)0.0591 (17)0.148 (2)0.073 (7)*
H250.352 (2)0.0051 (15)0.039 (2)0.073 (7)*
H260.405 (3)0.0240 (17)0.143 (2)0.089 (8)*
H310.1127 (19)0.0106 (13)0.110 (2)0.058 (5)*
H320.072 (2)0.0470 (16)0.241 (2)0.069 (6)*
H510.0254 (19)0.1239 (13)0.069 (2)0.060 (6)*
H520.075 (2)0.1731 (14)0.1822 (19)0.062 (6)*
H610.123 (3)0.2753 (16)0.308 (2)0.083 (7)*
H620.015 (3)0.2881 (19)0.304 (2)0.101 (9)*
H630.018 (2)0.2040 (15)0.371 (2)0.066 (6)*
H640.224 (3)0.2983 (16)0.071 (2)0.087 (7)*
H650.192 (2)0.2337 (15)0.018 (2)0.076 (7)*
H660.079 (3)0.2951 (17)0.067 (2)0.089 (8)*
H710.723 (3)0.372 (2)0.384 (3)0.113 (9)*
H720.583 (3)0.350 (2)0.314 (3)0.104 (11)*
H730.665 (4)0.318 (3)0.474 (5)0.21 (2)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.0416 (2)0.0528 (3)0.0593 (3)0.01223 (17)0.02488 (19)0.00821 (19)
O10.0495 (7)0.0680 (9)0.1266 (13)0.0205 (6)0.0476 (8)0.0190 (9)
O20.0384 (7)0.0967 (12)0.0918 (11)0.0102 (7)0.0168 (7)0.0035 (9)
O30.0763 (10)0.1010 (12)0.0639 (9)0.0328 (9)0.0363 (8)0.0025 (8)
N10.0373 (7)0.0457 (7)0.0611 (8)0.0070 (5)0.0248 (6)0.0067 (6)
N20.0429 (7)0.0615 (9)0.0631 (9)0.0147 (7)0.0244 (7)0.0016 (7)
C20.0440 (8)0.0423 (8)0.0568 (9)0.0010 (7)0.0272 (7)0.0022 (7)
C30.0500 (9)0.0393 (8)0.0639 (11)0.0053 (7)0.0287 (8)0.0020 (8)
C40.0386 (8)0.0520 (9)0.0550 (10)0.0093 (7)0.0218 (7)0.0009 (7)
C50.0435 (9)0.0501 (9)0.0667 (11)0.0008 (7)0.0327 (8)0.0037 (8)
C60.0456 (8)0.0391 (8)0.0524 (9)0.0013 (6)0.0264 (7)0.0039 (7)
C70.0424 (8)0.0468 (9)0.0589 (10)0.0045 (7)0.0252 (8)0.0020 (8)
C110.0357 (7)0.0419 (8)0.0547 (9)0.0017 (6)0.0201 (7)0.0019 (7)
C120.0369 (8)0.0586 (10)0.0491 (9)0.0084 (7)0.0147 (7)0.0074 (8)
C130.0411 (8)0.0580 (10)0.0465 (9)0.0055 (7)0.0196 (7)0.0017 (7)
C140.0340 (7)0.0432 (8)0.0508 (8)0.0031 (6)0.0178 (6)0.0024 (7)
C150.0431 (8)0.0547 (10)0.0461 (9)0.0087 (7)0.0133 (7)0.0039 (7)
C160.0480 (9)0.0552 (10)0.0475 (9)0.0063 (7)0.0209 (7)0.0007 (7)
C170.104 (2)0.0543 (13)0.147 (3)0.0241 (14)0.080 (2)0.0284 (16)
C210.0780 (14)0.0610 (12)0.0667 (12)0.0021 (11)0.0450 (12)0.0067 (10)
C220.0516 (11)0.0633 (13)0.0892 (17)0.0138 (9)0.0338 (11)0.0063 (11)
C610.0725 (13)0.0525 (11)0.0602 (12)0.0003 (10)0.0295 (10)0.0054 (9)
C620.0748 (13)0.0521 (11)0.0642 (12)0.0108 (10)0.0379 (11)0.0138 (9)
Geometric parameters (Å, º) top
S1—O31.4240 (16)C11—C121.393 (2)
S1—O21.4285 (16)C12—C131.382 (2)
S1—C171.755 (3)C12—H120.98 (2)
S1—C141.7674 (16)C13—C141.384 (2)
O1—N11.2832 (17)C13—H130.93 (2)
N1—C21.489 (2)C14—C151.382 (2)
N1—C61.496 (2)C15—C161.381 (2)
N2—C41.470 (2)C15—H150.97 (2)
N2—C71.254 (2)C16—H160.94 (2)
C2—C221.525 (3)C17—H711.01 (3)
C2—C31.528 (2)C17—H721.00 (3)
C2—C211.529 (3)C17—H730.96 (5)
C3—C41.515 (2)C21—H210.95 (3)
C3—H310.95 (2)C21—H220.99 (2)
C3—H320.92 (2)C21—H230.98 (3)
C4—C51.516 (3)C22—H240.96 (2)
C4—H40.968 (19)C22—H250.97 (2)
C5—C61.525 (2)C22—H260.96 (3)
C5—H510.98 (2)C61—H610.96 (3)
C5—H520.91 (2)C61—H621.01 (3)
C6—C621.522 (2)C61—H630.99 (2)
C6—C611.535 (3)C62—H640.99 (3)
C7—C111.474 (2)C62—H650.95 (2)
C7—H70.93 (2)C62—H661.00 (3)
C11—C161.387 (2)
O3—S1—O2116.69 (10)C13—C12—C11120.49 (15)
O3—S1—C17111.00 (17)C13—C12—H12121.9 (12)
O2—S1—C17107.55 (17)C11—C12—H12117.6 (12)
O3—S1—C14108.81 (8)C12—C13—C14118.88 (16)
O2—S1—C14108.23 (9)C12—C13—H13119.8 (13)
C17—S1—C14103.75 (11)C14—C13—H13121.4 (13)
O1—N1—C2115.95 (13)C15—C14—C13121.65 (15)
O1—N1—C6116.04 (13)C15—C14—S1118.17 (12)
C2—N1—C6124.70 (12)C13—C14—S1120.18 (13)
C7—N2—C4116.71 (16)C16—C15—C14118.84 (15)
N1—C2—C22107.25 (15)C16—C15—H15120.5 (12)
N1—C2—C3109.64 (13)C14—C15—H15120.6 (12)
C22—C2—C3109.26 (16)C15—C16—C11120.76 (16)
N1—C2—C21109.65 (15)C15—C16—H16120.5 (12)
C22—C2—C21109.61 (17)C11—C16—H16118.7 (12)
C3—C2—C21111.35 (16)S1—C17—H71109.1 (17)
C4—C3—C2113.58 (14)S1—C17—H7296.7 (18)
C4—C3—H31107.2 (12)H71—C17—H7294 (2)
C2—C3—H31110.3 (12)S1—C17—H73109 (3)
C4—C3—H32110.3 (14)H71—C17—H73117 (3)
C2—C3—H32108.8 (13)H72—C17—H73129 (3)
H31—C3—H32106.4 (18)C2—C21—H21111.0 (15)
N2—C4—C3108.94 (14)C2—C21—H22113.9 (13)
N2—C4—C5109.40 (14)H21—C21—H22104 (2)
C3—C4—C5107.88 (14)C2—C21—H23107.9 (14)
N2—C4—H4109.0 (11)H21—C21—H23111 (2)
C3—C4—H4109.4 (11)H22—C21—H23109.4 (19)
C5—C4—H4112.1 (11)C2—C22—H24110.9 (14)
C4—C5—C6113.34 (14)C2—C22—H25111.8 (13)
C4—C5—H51109.9 (12)H24—C22—H25105 (2)
C6—C5—H51109.8 (12)C2—C22—H26111.5 (15)
C4—C5—H52109.1 (13)H24—C22—H26109 (2)
C6—C5—H52107.1 (13)H25—C22—H26109 (2)
H51—C5—H52107.4 (17)C6—C61—H61111.5 (15)
N1—C6—C62107.78 (15)C6—C61—H62111.9 (15)
N1—C6—C5109.15 (13)H61—C61—H62107 (2)
C62—C6—C5109.79 (15)C6—C61—H63111.1 (12)
N1—C6—C61109.72 (14)H61—C61—H63106.1 (19)
C62—C6—C61108.45 (16)H62—C61—H63109 (2)
C5—C6—C61111.86 (16)C6—C62—H64111.0 (15)
N2—C7—C11123.36 (17)C6—C62—H65112.0 (14)
N2—C7—H7120.5 (13)H64—C62—H65109 (2)
C11—C7—H7116.0 (13)C6—C62—H66107.3 (14)
C16—C11—C12119.36 (15)H64—C62—H66111 (2)
C16—C11—C7119.11 (16)H65—C62—H66106 (2)
C12—C11—C7121.52 (15)
O1—N1—C2—C3166.73 (16)C4—C5—C6—C62165.52 (17)
O1—N1—C6—C5165.91 (16)C4—C5—C6—C6174.0 (2)
C6—N1—C2—C334.7 (2)C4—N2—C7—C11178.00 (15)
C2—N1—C6—C535.6 (2)N2—C7—C11—C16178.84 (18)
N1—C2—C3—C445.9 (2)N2—C7—C11—C120.3 (3)
C4—C5—C6—N147.6 (2)C16—C11—C12—C130.0 (3)
C2—C3—C4—C560.9 (2)C7—C11—C12—C13178.53 (16)
C3—C4—C5—C662.0 (2)C11—C12—C13—C141.2 (3)
C2—C3—C4—N2179.57 (15)C12—C13—C14—C151.3 (3)
N2—C4—C5—C6179.67 (15)C12—C13—C14—S1179.06 (13)
C7—N2—C4—C3109.25 (19)O3—S1—C14—C15176.55 (14)
C7—N2—C4—C5133.05 (18)O2—S1—C14—C1548.83 (17)
O1—N1—C2—C2248.2 (2)C17—S1—C14—C1565.2 (2)
C6—N1—C2—C22153.25 (16)O3—S1—C14—C133.83 (18)
O1—N1—C2—C2170.7 (2)O2—S1—C14—C13131.55 (15)
C6—N1—C2—C2187.80 (19)C17—S1—C14—C13114.4 (2)
C22—C2—C3—C4163.14 (17)C13—C14—C15—C160.2 (3)
C21—C2—C3—C475.6 (2)S1—C14—C15—C16179.86 (14)
O1—N1—C6—C6246.7 (2)C14—C15—C16—C111.0 (3)
C2—N1—C6—C62154.76 (16)C12—C11—C16—C151.2 (3)
O1—N1—C6—C6171.2 (2)C7—C11—C16—C15179.69 (16)
C2—N1—C6—C6187.33 (19)
 
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