TEMPO radicals showing magnetic interactions. I. 4-(4-Halobenzylideneamino)TEMPO and related compounds

X-ray crystal structure analyses of the 4-(4-halobenzyl­ideneamino)TEMPO (TEMPO = 2,2,6,6-tetramethyl­piperidyl-1-oxyl) radicals 4-(4-fluoro­benzyl­ideneamino)-2,2,6,6-tetramethylpiperidyl-1-oxyl, 4-(4-chlorobenzyl­ideneamino)-2,2,6,6-tetramethylpiperidyl-1-oxyl, 4-(4-bromobenzylideneamino)-2,2,6,6-tetramethylpiperidyl-1-oxyl and 4-(4-iodobenzylideneamino)-2,2,6,6-tetramethylpiperidyl-1-oxyl, and other 4-Ar—CH=N—TEMPO [Ar = 4-Ph-Ph, 2,2,6,6-tetramethyl-4-(4-phenylbenzylideneamino)piperidyl-1-oxyl, 4-Py, 2,2,6,6-tetramethyl-4-(4-pyridylmethylideneamino)piperidyl-1-oxyl, and 3,5-diCl-Ph, 4-(3,5-dichlorobenzylidene­amino)-2,2,6,6-tetramethylpiperidyl-1-oxyl] radicals have been performed at room temperature. Some of these radicals show intermolecular ferromagnetic interactions at extremely low temperatures. X-ray analysis revealed that crystals of the 4-I-Ph derivative showed two modifications [(a) and (b)]; measurements of the magnetic properties of these crystals showed a ferromagnetic transition at an extremely low temperature for modification (a) and an antiferromagnetic interaction for modification (b). The structural features of these TEMPO radical crystals can be classified into three groups: (i) the crystal structures of the 4-Cl-Ph, 4-I-Ph(a) and 4-Ph-Ph derivatives, which show a ferromagnetic transition; (ii) the structures of the 4-Br-Ph and 4-Py derivatives, which show a ferromagnetic interaction (θ > 0); (iii) miscellaneous: the antiferromagnetic 4-F-Ph and 4-I-Ph(b) derivatives (θ < 0) and the ferromagnetic 3,5-diCl-Ph (θ > 0) derivative. Sheet-like arrangements of O atoms and intra-sheet interactions through the CH₂ or CH₃ groups of the TEMPO rings are related to the mechanisms of the ferromagnetic interactions.

Computing details

Data collection: Rigaku/AFC Diffractometer Control for (1), (2), (4a), (4b), (6); MSC/AFC Diffractometer Control for (3), (5), (7). Cell refinement: Rigaku/AFC Diffractometer Control for (1), (2), (4a), (4b), (6); MSC/AFC Diffractometer Control for (3), (5), (7). For all compounds, data reduction: TEXSAN. Program(s) used to solve structure: SAPI91 for (1), (6); SIR88 for (2), (5), (7); DIRDIF92 for (3), (4a); DIRDIF92 (PATTY) for (4b). For all compounds, program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP II; software used to prepare material for publication: TEXSAN.

Figures

(1) 4-(4-fluorophenyl)methyleneamino-2,2,6,6-tetramethylpiperidin-1-oxyl

Crystal data

C16H22FN2O	F(000) = 1192.00
Mr = 277.36	Dx = 1.159 Mg m^−3
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 24 reflections
a = 20.0097 (13) Å	θ = 12.9–17.0°
b = 15.249 (2) Å	µ = 0.08 mm^−1
c = 10.4168 (18) Å	T = 296 K
V = 3178.4 (8) Å^3	Prism, orange
Z = 8	0.40 × 0.30 × 0.20 mm

Data collection

Rigaku AFC7R diffractometer	1948 reflections with I > 2σ(I)
Radiation source: Rigaku rotating anode	Rint = 0.000
Graphite monochromator	θmax = 27.5°, θmin = 2.6°
ω–2θ scans	h = 0→26
Absorption correction: ψ scans(north,Phillips & Mathews,1968) ?	k = 0→19
Tmin = 0.993, Tmax = 0.999	l = −13→0
3647 measured reflections	3 standard reflections every 150 reflections
3647 independent reflections	intensity decay: −0.3%

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.043	Hydrogen site location: difference Fourier map
wR(F^2) = 0.140	All H-atom parameters refined
S = 0.99	Calculated w = 1/[σ^2(Fo^2) + (0.0632P)^2 + 0.2539P] where P = (Fo^2 + 2Fc^2)/3
3647 reflections	(Δ/σ)max = 0.005
269 parameters	Δρmax = 0.11 e Å^−3
0 restraints	Δρmin = −0.20 e Å^−3

Special details

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

Refinement. Refinement 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 (Ų)

	x	y	z	Uiso*/Ueq
F1	−0.07687 (7)	0.18277 (9)	−0.22964 (12)	0.0977 (4)
O1	0.21003 (8)	0.01944 (10)	0.73277 (13)	0.0896 (5)
N1	0.18047 (7)	0.03940 (9)	0.62714 (13)	0.0592 (4)
N2	0.08721 (7)	0.10207 (11)	0.27581 (14)	0.0661 (4)
C2	0.20017 (9)	0.12437 (11)	0.56772 (16)	0.0590 (4)
C3	0.15145 (11)	0.14760 (12)	0.46079 (18)	0.0625 (5)
C4	0.13569 (9)	0.07210 (12)	0.37212 (16)	0.0583 (4)
C5	0.10388 (10)	0.00026 (13)	0.45138 (18)	0.0612 (5)
C6	0.14878 (9)	−0.03535 (10)	0.55699 (15)	0.0571 (4)
C7	0.09967 (9)	0.08762 (12)	0.15986 (17)	0.0598 (4)
C11	0.05404 (9)	0.11417 (11)	0.05609 (16)	0.0568 (4)
C12	−0.00342 (9)	0.16124 (12)	0.08352 (19)	0.0641 (5)
C13	−0.04745 (10)	0.18428 (14)	−0.0121 (2)	0.0709 (5)
C14	−0.03296 (10)	0.16035 (13)	−0.13430 (19)	0.0689 (5)
C15	0.02302 (13)	0.11541 (16)	−0.1664 (2)	0.0851 (6)
C16	0.06681 (11)	0.09242 (16)	−0.06965 (19)	0.0778 (6)
C21	0.19703 (17)	0.19394 (16)	0.6735 (3)	0.0841 (7)
C22	0.27175 (11)	0.11717 (18)	0.5171 (3)	0.0800 (6)
C61	0.20363 (13)	−0.09445 (15)	0.5031 (3)	0.0755 (6)
C62	0.10709 (15)	−0.08643 (17)	0.6540 (2)	0.0819 (6)
H4	0.1770 (10)	0.0516 (12)	0.3292 (17)	0.070 (5)*
H7	0.1398 (9)	0.0572 (12)	0.1347 (16)	0.066 (5)*
H12	−0.0127 (9)	0.1791 (11)	0.1695 (19)	0.063 (5)*
H13	−0.0889 (11)	0.2150 (15)	0.005 (2)	0.094 (7)*
H15	0.0332 (11)	0.0995 (14)	−0.255 (2)	0.088 (6)*
H16	0.1061 (10)	0.0617 (14)	−0.0899 (18)	0.081 (6)*
H21	0.1526 (14)	0.1945 (16)	0.712 (2)	0.107 (9)*
H22	0.2066 (11)	0.2515 (18)	0.631 (2)	0.101 (7)*
H23	0.2312 (14)	0.1813 (18)	0.734 (3)	0.118 (10)*
H24	0.2779 (12)	0.0756 (17)	0.449 (2)	0.106 (8)*
H25	0.2872 (11)	0.1775 (16)	0.488 (2)	0.094 (7)*
H26	0.3032 (12)	0.1026 (15)	0.589 (2)	0.101 (7)*
H31	0.1720 (9)	0.1959 (13)	0.4150 (18)	0.076 (6)*
H32	0.1084 (11)	0.1694 (13)	0.500 (2)	0.085 (6)*
H51	0.0934 (9)	−0.0457 (14)	0.3943 (18)	0.080 (6)*
H52	0.0627 (10)	0.0241 (13)	0.4906 (18)	0.076 (6)*
H61	0.2306 (11)	−0.0686 (15)	0.435 (2)	0.092 (7)*
H62	0.1856 (10)	−0.1480 (15)	0.468 (2)	0.088 (7)*
H63	0.2341 (12)	−0.1125 (16)	0.576 (2)	0.103 (8)*
H64	0.1391 (13)	−0.1165 (18)	0.720 (2)	0.111 (8)*
H65	0.0816 (12)	−0.1318 (16)	0.608 (2)	0.100 (8)*
H66	0.0754 (14)	−0.0499 (19)	0.696 (3)	0.124 (10)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
F1	0.1056 (9)	0.1075 (10)	0.0800 (8)	0.0021 (7)	−0.0372 (7)	0.0143 (7)
O1	0.1215 (12)	0.0861 (10)	0.0610 (8)	−0.0100 (9)	−0.0312 (8)	0.0149 (7)
N1	0.0714 (9)	0.0573 (8)	0.0489 (8)	−0.0046 (7)	−0.0083 (7)	0.0040 (6)
N2	0.0657 (9)	0.0830 (10)	0.0495 (9)	0.0119 (8)	−0.0024 (7)	0.0039 (7)
C2	0.0684 (10)	0.0513 (9)	0.0574 (10)	−0.0065 (8)	−0.0029 (9)	0.0024 (8)
C3	0.0715 (12)	0.0576 (10)	0.0584 (10)	0.0014 (9)	−0.0024 (9)	0.0097 (9)
C4	0.0551 (9)	0.0717 (11)	0.0482 (9)	0.0086 (8)	−0.0019 (8)	0.0046 (8)
C5	0.0623 (11)	0.0634 (11)	0.0579 (10)	−0.0055 (9)	−0.0043 (9)	−0.0051 (9)
C6	0.0677 (10)	0.0494 (9)	0.0543 (9)	−0.0028 (8)	0.0019 (8)	0.0021 (8)
C7	0.0573 (10)	0.0668 (11)	0.0553 (10)	0.0064 (9)	−0.0001 (8)	0.0036 (8)
C11	0.0598 (10)	0.0615 (10)	0.0490 (9)	−0.0015 (8)	0.0024 (8)	0.0038 (8)
C12	0.0691 (11)	0.0742 (11)	0.0490 (10)	0.0072 (9)	0.0055 (9)	0.0079 (9)
C13	0.0643 (11)	0.0805 (13)	0.0679 (12)	0.0104 (10)	−0.0005 (10)	0.0154 (10)
C14	0.0754 (12)	0.0692 (11)	0.0622 (11)	−0.0046 (9)	−0.0172 (10)	0.0123 (9)
C15	0.1018 (16)	0.1028 (16)	0.0505 (11)	0.0147 (14)	−0.0085 (12)	−0.0092 (11)
C16	0.0783 (13)	0.0980 (15)	0.0571 (12)	0.0215 (12)	−0.0037 (10)	−0.0084 (11)
C21	0.109 (2)	0.0642 (13)	0.0789 (15)	−0.0103 (13)	−0.0086 (16)	−0.0116 (12)
C22	0.0667 (12)	0.0841 (16)	0.0892 (16)	−0.0135 (11)	−0.0036 (12)	0.0054 (14)
C61	0.0887 (14)	0.0593 (12)	0.0786 (14)	0.0130 (11)	0.0034 (13)	0.0009 (11)
C62	0.0998 (17)	0.0681 (13)	0.0777 (15)	−0.0166 (13)	0.0129 (14)	0.0093 (12)

Geometric parameters (Å, º)

F1—C14	1.369 (2)	C11—C12	1.385 (3)
O1—N1	1.2858 (18)	C12—C13	1.376 (3)
N1—C2	1.489 (2)	C12—H12	0.955 (19)
N1—C6	1.495 (2)	C13—C14	1.355 (3)
N2—C7	1.253 (2)	C13—H13	0.97 (2)
N2—C4	1.468 (2)	C14—C15	1.355 (3)
C2—C3	1.522 (2)	C15—C16	1.380 (3)
C2—C22	1.530 (3)	C15—H15	0.98 (2)
C2—C21	1.531 (3)	C16—H16	0.94 (2)
C3—C4	1.509 (3)	C21—H21	0.98 (3)
C3—H31	0.97 (2)	C21—H22	1.00 (3)
C3—H32	1.01 (2)	C21—H23	0.95 (3)
C4—C5	1.512 (2)	C22—H24	0.96 (3)
C4—H4	0.991 (19)	C22—H25	1.02 (2)
C5—C6	1.521 (2)	C22—H26	1.00 (2)
C5—H51	0.94 (2)	C61—H61	0.98 (2)
C5—H52	0.99 (2)	C61—H62	0.97 (2)
C6—C62	1.525 (3)	C61—H63	1.01 (3)
C6—C61	1.527 (3)	C62—H64	1.05 (3)
C7—C11	1.472 (2)	C62—H65	0.98 (3)
C7—H7	0.964 (18)	C62—H66	0.95 (3)
C11—C16	1.375 (3)
O1···O1^i	5.4806 (14)	O1···C61^i	3.496 (3)
O1···O1^ii	7.7904 (14)	O1···H24^i	2.69 (3)
O1···C22^i	3.639 (3)	O1···H4^i	2.70 (2)
O1···C4^i	3.686 (2)	O1···H61^i	2.53 (3)
O1—N1—C2	116.10 (14)	C13—C12—C11	120.96 (18)
O1—N1—C6	115.65 (14)	C13—C12—H12	118.8 (11)
C2—N1—C6	124.92 (13)	C11—C12—H12	120.2 (11)
C7—N2—C4	118.20 (15)	C14—C13—C12	118.32 (19)
N1—C2—C3	109.71 (14)	C14—C13—H13	119.1 (14)
N1—C2—C22	109.18 (16)	C12—C13—H13	122.5 (14)
C3—C2—C22	111.34 (17)	C13—C14—C15	122.99 (18)
N1—C2—C21	107.03 (16)	C13—C14—F1	118.46 (19)
C3—C2—C21	109.83 (18)	C15—C14—F1	118.55 (18)
C22—C2—C21	109.65 (19)	C14—C15—C16	118.2 (2)
C4—C3—C2	113.83 (15)	C14—C15—H15	122.1 (13)
C4—C3—H31	111.5 (11)	C16—C15—H15	119.7 (13)
C2—C3—H31	105.3 (11)	C11—C16—C15	121.1 (2)
C4—C3—H32	108.7 (12)	C11—C16—H16	119.3 (12)
C2—C3—H32	109.1 (12)	C15—C16—H16	119.6 (12)
H31—C3—H32	108.2 (16)	C2—C21—H21	110.0 (15)
N2—C4—C3	108.58 (15)	C2—C21—H22	106.5 (13)
N2—C4—C5	108.69 (15)	H21—C21—H22	110 (2)
C3—C4—C5	107.84 (15)	C2—C21—H23	107.8 (17)
N2—C4—H4	110.0 (10)	H21—C21—H23	113 (2)
C3—C4—H4	110.0 (10)	H22—C21—H23	109 (2)
C5—C4—H4	111.7 (10)	C2—C22—H24	115.0 (15)
C4—C5—C6	113.89 (15)	C2—C22—H25	108.8 (12)
C4—C5—H51	106.7 (12)	H24—C22—H25	109.9 (19)
C6—C5—H51	108.8 (12)	C2—C22—H26	110.3 (13)
C4—C5—H52	108.0 (11)	H24—C22—H26	109 (2)
C6—C5—H52	109.0 (11)	H25—C22—H26	103.4 (18)
H51—C5—H52	110.4 (16)	C6—C61—H61	115.3 (13)
N1—C6—C5	109.39 (14)	C6—C61—H62	111.8 (12)
N1—C6—C62	107.31 (15)	H61—C61—H62	105.6 (18)
C5—C6—C62	109.80 (17)	C6—C61—H63	108.5 (14)
N1—C6—C61	108.95 (16)	H61—C61—H63	108.9 (18)
C5—C6—C61	111.68 (16)	H62—C61—H63	106.4 (19)
C62—C6—C61	109.61 (18)	C6—C62—H64	109.0 (14)
N2—C7—C11	122.43 (17)	C6—C62—H65	108.9 (14)
N2—C7—H7	120.8 (10)	H64—C62—H65	109 (2)
C11—C7—H7	116.7 (10)	C6—C62—H66	111.6 (16)
C16—C11—C12	118.40 (17)	H64—C62—H66	111 (2)
C16—C11—C7	121.19 (17)	H65—C62—H66	107 (2)
C12—C11—C7	120.40 (16)
O1—N1—C2—C3	−168.24 (16)	O1—N1—C6—C61	−69.67 (19)
C6—N1—C2—C3	33.3 (2)	C2—N1—C6—C61	88.9 (2)
O1—N1—C2—C22	69.5 (2)	C4—C5—C6—N1	46.1 (2)
C6—N1—C2—C22	−88.9 (2)	C4—C5—C6—C62	163.58 (18)
O1—N1—C2—C21	−49.1 (2)	C4—C5—C6—C61	−74.6 (2)
C6—N1—C2—C21	152.44 (19)	C4—N2—C7—C11	179.36 (16)
N1—C2—C3—C4	−45.7 (2)	N2—C7—C11—C16	−175.68 (19)
C22—C2—C3—C4	75.2 (2)	N2—C7—C11—C12	3.7 (3)
C21—C2—C3—C4	−163.13 (18)	C16—C11—C12—C13	1.3 (3)
C7—N2—C4—C3	129.56 (18)	C7—C11—C12—C13	−178.12 (18)
C7—N2—C4—C5	−113.38 (19)	C11—C12—C13—C14	−0.5 (3)
C2—C3—C4—N2	178.58 (15)	C12—C13—C14—C15	−0.5 (3)
C2—C3—C4—C5	61.0 (2)	C12—C13—C14—F1	179.66 (17)
N2—C4—C5—C6	−178.85 (15)	C13—C14—C15—C16	0.6 (4)
C3—C4—C5—C6	−61.3 (2)	F1—C14—C15—C16	−179.5 (2)
O1—N1—C6—C5	168.00 (15)	C12—C11—C16—C15	−1.1 (3)
C2—N1—C6—C5	−33.5 (2)	C7—C11—C16—C15	178.3 (2)
O1—N1—C6—C62	48.9 (2)	C14—C15—C16—C11	0.2 (4)
C2—N1—C6—C62	−152.55 (18)

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

(2) 4-(4-chlorophenyl)methyleneamino-2,2,6,6-tetramethylpiperidin-1-oxyl

Crystal data

C16H22ClN2O	F(000) = 628.00
Mr = 293.81	Dx = 1.229 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 5.8845 (19) Å	Cell parameters from 25 reflections
b = 24.417 (2) Å	θ = 12.7–17.2°
c = 11.397 (2) Å	µ = 0.24 mm^−1
β = 104.09 (2)°	T = 293 K
V = 1588.3 (6) Å^3	Prism, orange
Z = 4	0.52 × 0.15 × 0.10 mm

Data collection

Rigaku AFC7R diffractometer	2383 reflections with I > 2σ(I)
Radiation source: Rigaku rotating anode	Rint = 0.018
Graphite monochromator	θmax = 27.5°, θmin = 2.0°
ω–2θ scans	h = 0→7
Absorption correction: integration ?	k = 0→31
Tmin = 0.963, Tmax = 0.978	l = −14→14
3996 measured reflections	3 standard reflections every 150 reflections
3653 independent reflections	intensity decay: −0.1%

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.040	Hydrogen site location: difference Fourier map
wR(F^2) = 0.119	All H-atom parameters refined
S = 0.99	Calculated w = 1/[σ^2(Fo^2) + (0.0456P)^2 + 0.3805P] where P = (Fo^2 + 2Fc^2)/3
3653 reflections	(Δ/σ)max = 0.001
269 parameters	Δρmax = 0.16 e Å^−3
0 restraints	Δρmin = −0.23 e Å^−3

Special details

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

Refinement. Refinement 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 (Ų)

	x	y	z	Uiso*/Ueq
Cl1	0.44430 (12)	0.00565 (2)	−0.32069 (5)	0.0765 (2)
O1	−0.2174 (3)	0.21540 (6)	0.50610 (12)	0.0602 (4)
N1	−0.1091 (2)	0.19397 (6)	0.43244 (12)	0.0425 (3)
N2	0.1741 (3)	0.11743 (6)	0.16952 (13)	0.0472 (4)
C2	−0.0536 (3)	0.23162 (7)	0.33992 (15)	0.0437 (4)
C3	0.0055 (3)	0.19770 (7)	0.23834 (15)	0.0437 (4)
C4	0.1674 (3)	0.14925 (7)	0.27834 (15)	0.0425 (4)
C5	0.0656 (4)	0.11284 (8)	0.36107 (17)	0.0477 (4)
C6	0.0208 (3)	0.14195 (8)	0.47216 (15)	0.0461 (4)
C7	0.3553 (3)	0.11993 (8)	0.13015 (15)	0.0440 (4)
C11	0.3763 (3)	0.09147 (7)	0.01895 (15)	0.0421 (4)
C12	0.2109 (4)	0.05370 (8)	−0.03742 (19)	0.0559 (5)
C13	0.2299 (4)	0.02727 (9)	−0.1417 (2)	0.0634 (6)
C14	0.4162 (4)	0.03928 (7)	−0.18984 (16)	0.0496 (4)
C15	0.5824 (4)	0.07696 (10)	−0.13745 (18)	0.0592 (5)
C16	0.5622 (4)	0.10271 (10)	−0.03214 (18)	0.0582 (5)
C21	0.1489 (4)	0.26969 (10)	0.4004 (2)	0.0601 (6)
C22	−0.2722 (4)	0.26557 (10)	0.2880 (2)	0.0593 (5)
C61	0.2493 (4)	0.15481 (11)	0.56646 (19)	0.0615 (6)
C62	−0.1350 (5)	0.10608 (10)	0.5300 (2)	0.0615 (6)
H4	0.331 (3)	0.1605 (7)	0.3202 (16)	0.045 (5)*
H7	0.494 (4)	0.1404 (9)	0.1721 (19)	0.069 (6)*
H12	0.084 (4)	0.0469 (10)	−0.003 (2)	0.079 (7)*
H13	0.123 (5)	0.0011 (11)	−0.176 (2)	0.093 (9)*
H15	0.711 (4)	0.0845 (9)	−0.170 (2)	0.070 (6)*
H16	0.684 (4)	0.1270 (9)	0.006 (2)	0.072 (7)*
H21	0.303 (4)	0.2494 (10)	0.426 (2)	0.076 (7)*
H22	0.108 (4)	0.2882 (9)	0.469 (2)	0.073 (7)*
H23	0.164 (4)	0.2970 (9)	0.344 (2)	0.070 (7)*
H24	−0.303 (4)	0.2892 (9)	0.350 (2)	0.075 (7)*
H25	−0.408 (4)	0.2405 (10)	0.2570 (19)	0.072 (7)*
H26	−0.239 (4)	0.2875 (10)	0.226 (2)	0.082 (7)*
H31	0.077 (3)	0.2223 (7)	0.1914 (16)	0.045 (5)*
H32	−0.143 (4)	0.1837 (8)	0.1844 (18)	0.059 (6)*
H51	0.167 (3)	0.0812 (8)	0.3883 (17)	0.055 (5)*
H52	−0.086 (4)	0.0980 (9)	0.3139 (18)	0.060 (6)*
H61	0.366 (4)	0.1753 (9)	0.532 (2)	0.070 (6)*
H62	0.321 (4)	0.1207 (10)	0.598 (2)	0.080 (7)*
H63	0.202 (4)	0.1782 (11)	0.630 (2)	0.090 (8)*
H64	−0.058 (4)	0.0708 (10)	0.548 (2)	0.074 (7)*
H65	−0.163 (4)	0.1206 (9)	0.606 (2)	0.069 (6)*
H66	−0.291 (5)	0.1003 (10)	0.476 (2)	0.079 (7)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cl1	0.1119 (5)	0.0640 (3)	0.0616 (3)	0.0100 (3)	0.0367 (3)	−0.0164 (3)
O1	0.0767 (9)	0.0637 (8)	0.0516 (7)	0.0054 (7)	0.0377 (7)	−0.0024 (6)
N1	0.0476 (8)	0.0464 (8)	0.0371 (7)	−0.0030 (6)	0.0173 (6)	−0.0036 (6)
N2	0.0469 (8)	0.0516 (9)	0.0457 (8)	−0.0011 (7)	0.0164 (7)	−0.0106 (7)
C2	0.0535 (10)	0.0439 (9)	0.0383 (8)	−0.0020 (8)	0.0201 (7)	−0.0017 (7)
C3	0.0506 (10)	0.0471 (10)	0.0356 (8)	−0.0026 (8)	0.0150 (7)	−0.0027 (7)
C4	0.0427 (9)	0.0492 (10)	0.0371 (8)	−0.0031 (8)	0.0124 (7)	−0.0087 (7)
C5	0.0546 (11)	0.0438 (10)	0.0476 (10)	0.0012 (9)	0.0181 (9)	−0.0016 (8)
C6	0.0520 (10)	0.0482 (10)	0.0404 (9)	−0.0013 (8)	0.0155 (8)	0.0039 (7)
C7	0.0441 (9)	0.0484 (10)	0.0400 (9)	−0.0011 (8)	0.0113 (7)	−0.0021 (7)
C11	0.0445 (9)	0.0426 (9)	0.0401 (8)	0.0050 (7)	0.0119 (7)	0.0005 (7)
C12	0.0572 (12)	0.0538 (11)	0.0634 (12)	−0.0093 (9)	0.0278 (10)	−0.0111 (9)
C13	0.0722 (14)	0.0547 (12)	0.0683 (13)	−0.0150 (11)	0.0265 (11)	−0.0200 (10)
C14	0.0661 (12)	0.0418 (9)	0.0432 (9)	0.0120 (9)	0.0179 (8)	−0.0016 (7)
C15	0.0559 (12)	0.0771 (14)	0.0506 (11)	−0.0020 (11)	0.0246 (9)	−0.0046 (10)
C16	0.0512 (11)	0.0764 (14)	0.0498 (10)	−0.0124 (10)	0.0174 (9)	−0.0122 (10)
C21	0.0779 (15)	0.0557 (12)	0.0539 (11)	−0.0217 (11)	0.0301 (11)	−0.0130 (10)
C22	0.0743 (14)	0.0553 (12)	0.0554 (12)	0.0132 (11)	0.0293 (11)	0.0057 (10)
C61	0.0623 (13)	0.0752 (16)	0.0442 (11)	0.0033 (12)	0.0075 (10)	0.0061 (10)
C62	0.0766 (16)	0.0566 (13)	0.0593 (13)	−0.0048 (12)	0.0322 (12)	0.0075 (10)

Geometric parameters (Å, º)

Cl1—C14	1.7452 (18)	C11—C16	1.386 (3)
O1—N1	1.2829 (17)	C12—C13	1.381 (3)
N1—C2	1.494 (2)	C12—H12	0.94 (2)
N1—C6	1.495 (2)	C13—C14	1.372 (3)
N2—C7	1.255 (2)	C13—H13	0.91 (3)
N2—C4	1.472 (2)	C14—C15	1.369 (3)
C2—C22	1.524 (3)	C15—C16	1.385 (3)
C2—C3	1.531 (2)	C15—H15	0.94 (2)
C2—C21	1.536 (3)	C16—H16	0.95 (2)
C3—C4	1.517 (2)	C21—H21	1.01 (2)
C3—H31	0.967 (18)	C21—H22	0.98 (2)
C3—H32	1.00 (2)	C21—H23	0.94 (2)
C4—C5	1.521 (2)	C22—H24	0.96 (2)
C4—H4	1.006 (18)	C22—H25	1.00 (2)
C5—C6	1.530 (2)	C22—H26	0.94 (3)
C5—H51	0.98 (2)	C61—H61	1.00 (2)
C5—H52	0.99 (2)	C61—H62	0.96 (3)
C6—C62	1.529 (3)	C61—H63	1.02 (3)
C6—C61	1.535 (3)	C62—H64	0.97 (2)
C7—C11	1.477 (2)	C62—H65	0.99 (2)
C7—H7	0.98 (2)	C62—H66	0.98 (3)
C11—C12	1.380 (3)
O1···O1^i	5.8845 (19)	O1···H61^i	2.72 (2)
O1···O1^ii	5.9437 (13)	O1···H21^i	2.87 (3)
O1···C22^ii	3.339 (3)	O1···H26^ii	2.54 (3)
O1···C3^ii	3.397 (2)	O1···H31^ii	2.83 (2)
O1—N1—C2	116.09 (14)	C11—C12—C13	121.15 (19)
O1—N1—C6	116.58 (13)	C11—C12—H12	117.6 (14)
C2—N1—C6	123.59 (13)	C13—C12—H12	121.3 (14)
C7—N2—C4	118.37 (15)	C14—C13—C12	119.0 (2)
N1—C2—C22	107.46 (15)	C14—C13—H13	120.7 (16)
N1—C2—C3	109.26 (14)	C12—C13—H13	120.2 (16)
C22—C2—C3	109.06 (15)	C15—C14—C13	121.64 (18)
N1—C2—C21	109.54 (15)	C15—C14—Cl1	118.87 (15)
C22—C2—C21	109.53 (18)	C13—C14—Cl1	119.49 (16)
C3—C2—C21	111.89 (15)	C14—C15—C16	118.69 (19)
C4—C3—C2	115.86 (14)	C14—C15—H15	121.0 (14)
C4—C3—H31	108.8 (11)	C16—C15—H15	120.3 (14)
C2—C3—H31	107.0 (11)	C15—C16—C11	121.1 (2)
C4—C3—H32	108.0 (12)	C15—C16—H16	117.6 (13)
C2—C3—H32	108.9 (11)	C11—C16—H16	121.2 (13)
H31—C3—H32	107.9 (15)	C2—C21—H21	112.1 (14)
N2—C4—C3	107.58 (14)	C2—C21—H22	108.8 (13)
N2—C4—C5	108.01 (14)	H21—C21—H22	112.0 (19)
C3—C4—C5	109.21 (15)	C2—C21—H23	108.2 (14)
N2—C4—H4	108.9 (10)	H21—C21—H23	108.4 (19)
C3—C4—H4	112.9 (10)	H22—C21—H23	107.2 (18)
C5—C4—H4	110.0 (10)	C2—C22—H24	109.5 (14)
C4—C5—C6	114.50 (15)	C2—C22—H25	109.4 (13)
C4—C5—H51	110.9 (11)	H24—C22—H25	110.3 (19)
C6—C5—H51	108.6 (11)	C2—C22—H26	107.0 (15)
C4—C5—H52	108.4 (12)	H24—C22—H26	108.6 (19)
C6—C5—H52	107.9 (12)	H25—C22—H26	112.0 (19)
H51—C5—H52	106.2 (16)	C6—C61—H61	113.2 (12)
N1—C6—C62	107.54 (16)	C6—C61—H62	108.4 (14)
N1—C6—C5	108.83 (14)	H61—C61—H62	107.5 (19)
C62—C6—C5	109.46 (16)	C6—C61—H63	105.8 (14)
N1—C6—C61	109.53 (16)	H61—C61—H63	109.4 (19)
C62—C6—C61	109.27 (17)	H62—C61—H63	112.8 (19)
C5—C6—C61	112.10 (17)	C6—C62—H64	107.5 (14)
N2—C7—C11	122.68 (17)	C6—C62—H65	114.7 (13)
N2—C7—H7	122.2 (12)	H64—C62—H65	107.6 (18)
C11—C7—H7	115.1 (12)	C6—C62—H66	112.2 (14)
C12—C11—C16	118.42 (17)	H64—C62—H66	109 (2)
C12—C11—C7	121.13 (16)	H65—C62—H66	105.8 (18)
C16—C11—C7	120.44 (17)
O1—N1—C2—C22	−44.9 (2)	O1—N1—C6—C61	−76.20 (19)
C6—N1—C2—C22	157.69 (16)	C2—N1—C6—C61	81.11 (19)
O1—N1—C2—C3	−163.09 (15)	C4—C5—C6—N1	48.7 (2)
C6—N1—C2—C3	39.5 (2)	C4—C5—C6—C62	165.92 (18)
O1—N1—C2—C21	74.0 (2)	C4—C5—C6—C61	−72.7 (2)
C6—N1—C2—C21	−83.4 (2)	C4—N2—C7—C11	−177.42 (15)
N1—C2—C3—C4	−44.4 (2)	N2—C7—C11—C12	−10.1 (3)
C22—C2—C3—C4	−161.62 (17)	N2—C7—C11—C16	169.04 (19)
C21—C2—C3—C4	77.0 (2)	C16—C11—C12—C13	0.5 (3)
C7—N2—C4—C3	106.40 (19)	C7—C11—C12—C13	179.69 (19)
C7—N2—C4—C5	−135.83 (18)	C11—C12—C13—C14	−0.4 (4)
C2—C3—C4—N2	171.59 (15)	C12—C13—C14—C15	−0.4 (3)
C2—C3—C4—C5	54.6 (2)	C12—C13—C14—Cl1	179.30 (17)
N2—C4—C5—C6	−173.40 (15)	C13—C14—C15—C16	1.0 (3)
C3—C4—C5—C6	−56.7 (2)	Cl1—C14—C15—C16	−178.63 (17)
O1—N1—C6—C62	42.4 (2)	C14—C15—C16—C11	−1.0 (3)
C2—N1—C6—C62	−160.24 (16)	C12—C11—C16—C15	0.2 (3)
O1—N1—C6—C5	160.93 (15)	C7—C11—C16—C15	−179.00 (19)
C2—N1—C6—C5	−41.8 (2)

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

(3) 4-(4-bromophenyl)methyleneamino-2,2,6,6-tetramethylpiperidin-1-oxyl

Crystal data

C16H22BrN2O	F(000) = 700.00
Mr = 338.27	Dx = 1.350 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 7.541 (1) Å	Cell parameters from 25 reflections
b = 20.848 (3) Å	θ = 13.1–17.3°
c = 10.591 (1) Å	µ = 2.47 mm^−1
β = 91.56 (1)°	T = 295 K
V = 1664.4 (3) Å^3	Prism, orange
Z = 4	0.23 × 0.20 × 0.18 mm

Data collection

Rigaku AFC5R diffractometer	1867 reflections with I > 2σ(I)
Radiation source: Rigaku rotating anode	Rint = 0.035
Graphite monochromator	θmax = 27.5°, θmin = 2.7°
ω–2θ scans	h = 0→9
Absorption correction: integration ?	k = 0→27
Tmin = 0.521, Tmax = 0.701	l = −13→13
4102 measured reflections	3 standard reflections every 100 reflections
3822 independent reflections	intensity decay: −1.8%

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.046	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.098	All H-atom parameters refined
S = 0.97	Calculated w = 1/[σ^2(Fo^2) + (0.029P)^2 + 0.7762P] where P = (Fo^2 + 2Fc^2)/3
3822 reflections	(Δ/σ)max = 0.001
269 parameters	Δρmax = 0.23 e Å^−3
0 restraints	Δρmin = −0.29 e Å^−3

Special details

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

Refinement. Refinement 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 (Ų)

	x	y	z	Uiso*/Ueq
Br1	0.04002 (6)	−0.00432 (3)	−0.32787 (4)	0.07052 (18)
O1	0.7671 (3)	0.18407 (12)	0.6672 (2)	0.0582 (7)
N1	0.6809 (4)	0.16653 (13)	0.5667 (2)	0.0420 (7)
N2	0.4062 (4)	0.10603 (15)	0.2352 (3)	0.0528 (9)
C2	0.7232 (5)	0.20214 (17)	0.4497 (3)	0.0429 (9)
C3	0.6424 (6)	0.1681 (2)	0.3340 (4)	0.0499 (11)
C4	0.4557 (6)	0.14357 (19)	0.3488 (3)	0.0464 (10)
C5	0.4533 (6)	0.0993 (2)	0.4618 (4)	0.0498 (10)
C6	0.5125 (5)	0.13049 (18)	0.5865 (3)	0.0445 (9)
C7	0.2773 (5)	0.1257 (2)	0.1683 (3)	0.0478 (10)
C11	0.2172 (4)	0.09224 (18)	0.0517 (3)	0.0416 (9)
C12	0.0957 (6)	0.1218 (2)	−0.0298 (4)	0.0564 (11)
C13	0.0412 (6)	0.0932 (2)	−0.1429 (4)	0.0558 (11)
C14	0.1084 (5)	0.03442 (19)	−0.1713 (3)	0.0450 (9)
C15	0.2255 (5)	0.0026 (2)	−0.0916 (3)	0.0502 (9)
C16	0.2797 (5)	0.03280 (19)	0.0195 (3)	0.0466 (10)
C21	0.9252 (7)	0.2028 (3)	0.4394 (5)	0.0660 (13)
C22	0.6520 (7)	0.2709 (2)	0.4599 (4)	0.0580 (12)
C61	0.3741 (7)	0.1770 (3)	0.6343 (5)	0.0616 (12)
C62	0.5501 (8)	0.0791 (2)	0.6850 (5)	0.0636 (13)
H4	0.374 (4)	0.1782 (16)	0.356 (3)	0.044 (10)*
H7	0.225 (4)	0.1630 (17)	0.192 (3)	0.047 (11)*
H12	0.056 (4)	0.1608 (17)	−0.010 (3)	0.046 (11)*
H13	−0.043 (5)	0.112 (2)	−0.195 (4)	0.080 (14)*
H15	0.277 (5)	−0.0353 (17)	−0.111 (3)	0.051 (11)*
H16	0.356 (5)	0.0106 (17)	0.076 (3)	0.063 (11)*
H21	0.972 (5)	0.158 (2)	0.437 (4)	0.075 (15)*
H22	0.952 (5)	0.2239 (17)	0.361 (3)	0.056 (11)*
H23	0.977 (6)	0.224 (2)	0.509 (4)	0.091 (15)*
H24	0.514 (6)	0.2746 (19)	0.457 (3)	0.078 (15)*
H25	0.696 (4)	0.2904 (16)	0.532 (3)	0.048 (10)*
H26	0.683 (4)	0.2947 (16)	0.390 (3)	0.047 (10)*
H31	0.705 (4)	0.1325 (16)	0.315 (3)	0.038 (10)*
H32	0.648 (4)	0.1996 (16)	0.260 (3)	0.050 (10)*
H51	0.343 (5)	0.0812 (17)	0.474 (3)	0.051 (11)*
H52	0.529 (4)	0.0621 (16)	0.448 (3)	0.038 (10)*
H61	0.276 (5)	0.1548 (17)	0.660 (3)	0.051 (12)*
H62	0.419 (6)	0.201 (2)	0.714 (4)	0.103 (16)*
H63	0.338 (5)	0.212 (2)	0.577 (4)	0.077 (14)*
H64	0.641 (5)	0.051 (2)	0.668 (4)	0.071 (16)*
H65	0.445 (5)	0.0547 (18)	0.692 (3)	0.058 (13)*
H66	0.596 (5)	0.1020 (19)	0.768 (4)	0.083 (14)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Br1	0.0711 (3)	0.0913 (4)	0.0482 (2)	−0.0033 (3)	−0.01685 (17)	−0.0220 (2)
O1	0.0665 (18)	0.0658 (19)	0.0412 (14)	−0.0143 (15)	−0.0209 (12)	0.0031 (13)
N1	0.0487 (19)	0.0412 (19)	0.0355 (16)	−0.0042 (15)	−0.0094 (13)	0.0031 (13)
N2	0.061 (2)	0.055 (2)	0.0424 (17)	0.0019 (17)	−0.0141 (16)	−0.0114 (15)
C2	0.050 (2)	0.042 (2)	0.0363 (19)	−0.0053 (19)	−0.0031 (16)	−0.0011 (16)
C3	0.061 (3)	0.051 (3)	0.038 (2)	−0.001 (2)	0.0021 (19)	−0.005 (2)
C4	0.055 (2)	0.047 (2)	0.036 (2)	0.002 (2)	−0.0145 (18)	−0.0108 (17)
C5	0.050 (3)	0.053 (3)	0.046 (2)	−0.011 (2)	−0.0046 (19)	0.000 (2)
C6	0.047 (2)	0.049 (2)	0.0377 (19)	−0.008 (2)	−0.0051 (17)	0.0008 (17)
C7	0.053 (3)	0.049 (3)	0.041 (2)	0.001 (2)	−0.0036 (18)	−0.0045 (19)
C11	0.040 (2)	0.051 (3)	0.0329 (17)	−0.0023 (19)	−0.0061 (15)	−0.0005 (17)
C12	0.066 (3)	0.049 (3)	0.054 (2)	0.013 (2)	−0.016 (2)	−0.009 (2)
C13	0.055 (3)	0.063 (3)	0.049 (2)	0.004 (2)	−0.019 (2)	0.003 (2)
C14	0.044 (2)	0.055 (3)	0.0356 (18)	−0.0047 (19)	−0.0045 (16)	−0.0050 (17)
C15	0.056 (2)	0.048 (3)	0.046 (2)	0.009 (2)	−0.0068 (17)	−0.009 (2)
C16	0.047 (2)	0.052 (3)	0.040 (2)	0.008 (2)	−0.0114 (17)	0.0006 (18)
C21	0.065 (3)	0.069 (4)	0.064 (3)	−0.018 (3)	0.005 (3)	−0.005 (3)
C22	0.090 (4)	0.044 (3)	0.039 (2)	−0.002 (3)	−0.007 (2)	0.003 (2)
C61	0.055 (3)	0.074 (4)	0.055 (3)	0.001 (3)	0.003 (2)	−0.002 (3)
C62	0.071 (3)	0.064 (3)	0.056 (3)	−0.014 (3)	−0.011 (2)	0.018 (2)

Geometric parameters (Å, º)

Br1—C14	1.903 (3)	C11—C12	1.386 (5)
O1—N1	1.286 (3)	C12—C13	1.390 (5)
N1—C2	1.486 (4)	C12—H12	0.89 (3)
N1—C6	1.495 (4)	C13—C14	1.363 (5)
N2—C7	1.256 (4)	C13—H13	0.92 (4)
N2—C4	1.474 (4)	C14—C15	1.376 (5)
C2—C3	1.529 (5)	C15—C16	1.386 (5)
C2—C21	1.531 (6)	C15—H15	0.91 (3)
C2—C22	1.534 (5)	C16—H16	0.94 (4)
C3—C4	1.510 (5)	C21—H21	1.01 (4)
C3—H31	0.91 (3)	C21—H22	0.97 (4)
C3—H32	1.02 (3)	C21—H23	0.93 (5)
C4—C5	1.512 (5)	C22—H24	1.05 (4)
C4—H4	0.95 (3)	C22—H25	0.91 (3)
C5—C6	1.527 (5)	C22—H26	0.93 (3)
C5—H51	0.93 (3)	C61—H61	0.92 (3)
C5—H52	0.98 (3)	C61—H62	1.03 (5)
C6—C62	1.516 (5)	C61—H63	0.98 (4)
C6—C61	1.522 (6)	C62—H64	0.92 (4)
C7—C11	1.479 (5)	C62—H65	0.95 (4)
C7—H7	0.91 (3)	C62—H66	1.05 (4)
C11—C16	1.372 (5)
O1···O1^i	7.541 (1)	O1···C3^ii	3.687 (5)
O1···O1^ii	5.966 (2)	O1···H26^ii	2.49 (4)
O1···C22^ii	3.376 (5)	O1···H32^ii	2.78 (3)
O1—N1—C2	115.7 (3)	C11—C12—C13	121.4 (4)
O1—N1—C6	116.0 (3)	C11—C12—H12	118 (2)
C2—N1—C6	124.8 (3)	C13—C12—H12	120 (2)
C7—N2—C4	117.5 (3)	C14—C13—C12	118.2 (4)
N1—C2—C3	110.3 (3)	C14—C13—H13	120 (3)
N1—C2—C21	107.5 (3)	C12—C13—H13	122 (3)
C3—C2—C21	108.8 (3)	C13—C14—C15	122.3 (3)
N1—C2—C22	108.9 (3)	C13—C14—Br1	118.7 (3)
C3—C2—C22	110.9 (3)	C15—C14—Br1	119.0 (3)
C21—C2—C22	110.3 (4)	C14—C15—C16	118.2 (4)
C4—C3—C2	115.3 (3)	C14—C15—H15	123 (2)
C4—C3—H31	104 (2)	C16—C15—H15	118 (2)
C2—C3—H31	111 (2)	C11—C16—C15	121.7 (4)
C4—C3—H32	110.7 (19)	C11—C16—H16	120 (2)
C2—C3—H32	106.9 (19)	C15—C16—H16	118 (2)
H31—C3—H32	109 (3)	C2—C21—H21	110 (2)
N2—C4—C3	108.1 (3)	C2—C21—H22	107 (2)
N2—C4—C5	108.3 (3)	H21—C21—H22	109 (3)
C3—C4—C5	108.7 (3)	C2—C21—H23	110 (3)
N2—C4—H4	108.5 (19)	H21—C21—H23	109 (4)
C3—C4—H4	111 (2)	H22—C21—H23	111 (3)
C5—C4—H4	112 (2)	C2—C22—H24	115 (2)
C4—C5—C6	114.5 (3)	C2—C22—H25	111 (2)
C4—C5—H51	113 (2)	H24—C22—H25	109 (3)
C6—C5—H51	107 (2)	C2—C22—H26	110 (2)
C4—C5—H52	110.4 (19)	H24—C22—H26	102 (3)
C6—C5—H52	108.1 (18)	H25—C22—H26	109 (3)
H51—C5—H52	103 (3)	C6—C61—H61	110 (2)
N1—C6—C62	107.9 (3)	C6—C61—H62	112 (3)
N1—C6—C61	108.6 (3)	H61—C61—H62	105 (3)
C62—C6—C61	109.7 (4)	C6—C61—H63	117 (2)
N1—C6—C5	108.8 (3)	H61—C61—H63	110 (3)
C62—C6—C5	109.8 (3)	H62—C61—H63	103 (3)
C61—C6—C5	111.9 (3)	C6—C62—H64	116 (3)
N2—C7—C11	122.1 (4)	C6—C62—H65	107 (2)
N2—C7—H7	117 (2)	H64—C62—H65	108 (4)
C11—C7—H7	121 (2)	C6—C62—H66	108 (2)
C16—C11—C12	118.2 (3)	H64—C62—H66	103 (3)
C16—C11—C7	122.3 (3)	H65—C62—H66	116 (3)
C12—C11—C7	119.5 (4)
O1—N1—C2—C3	168.2 (3)	O1—N1—C6—C5	−165.9 (3)
C6—N1—C2—C3	−33.8 (5)	C2—N1—C6—C5	36.3 (5)
O1—N1—C2—C21	49.8 (4)	C4—C5—C6—N1	−47.7 (5)
C6—N1—C2—C21	−152.3 (3)	C4—C5—C6—C62	−165.6 (4)
O1—N1—C2—C22	−69.8 (4)	C4—C5—C6—C61	72.3 (5)
C6—N1—C2—C22	88.1 (4)	C4—N2—C7—C11	179.4 (3)
N1—C2—C3—C4	42.5 (5)	N2—C7—C11—C16	10.1 (6)
C21—C2—C3—C4	160.2 (4)	N2—C7—C11—C12	−168.8 (4)
C22—C2—C3—C4	−78.2 (5)	C16—C11—C12—C13	−1.7 (6)
C7—N2—C4—C3	−118.0 (4)	C7—C11—C12—C13	177.3 (4)
C7—N2—C4—C5	124.4 (4)	C11—C12—C13—C14	1.0 (6)
C2—C3—C4—N2	−173.7 (3)	C12—C13—C14—C15	0.8 (6)
C2—C3—C4—C5	−56.3 (5)	C12—C13—C14—Br1	−178.3 (3)
N2—C4—C5—C6	176.6 (4)	C13—C14—C15—C16	−1.9 (6)
C3—C4—C5—C6	59.4 (5)	Br1—C14—C15—C16	177.3 (3)
O1—N1—C6—C62	−46.8 (4)	C12—C11—C16—C15	0.6 (6)
C2—N1—C6—C62	155.4 (4)	C7—C11—C16—C15	−178.3 (4)
O1—N1—C6—C61	72.1 (4)	C14—C15—C16—C11	1.1 (6)
C2—N1—C6—C61	−85.7 (4)

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

(4a) 4-(4-iodophenyl)methyleneamino-2,2,6,6-tetramethylpiperidin-1-oxyl

Crystal data

C16H22IN2O	F(000) = 772.00
Mr = 385.27	Dx = 1.539 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 5.889 (4) Å	Cell parameters from 24 reflections
b = 25.851 (3) Å	θ = 12.7–16.1°
c = 11.322 (3) Å	µ = 1.93 mm^−1
β = 105.27 (3)°	T = 293 K
V = 1662.7 (13) Å^3	Plate, orange
Z = 4	0.50 × 0.19 × 0.04 mm

Data collection

Rigaku AFC7R diffractometer	2469 reflections with I > 2σ(I)
Radiation source: Rigaku rotating anode	Rint = 0.020
Graphite monochromator	θmax = 27.5°, θmin = 2.0°
ω–2θ scans	h = 0→7
Absorption correction: analytical ?	k = 0→33
Tmin = 0.708, Tmax = 0.926	l = −14→14
4201 measured reflections	3 standard reflections every 150 reflections
3843 independent reflections	intensity decay: −0.4%

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.033	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.095	All H-atom parameters refined
S = 0.99	Calculated w = 1/[σ^2(Fo^2) + (0.0287P)^2 + 0.8733P] where P = (Fo^2 + 2Fc^2)/3
3843 reflections	(Δ/σ)max = 0.002
269 parameters	Δρmax = 0.41 e Å^−3
0 restraints	Δρmin = −0.81 e Å^−3

Special details

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

Refinement. Refinement 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 (Ų)

	x	y	z	Uiso*/Ueq
I1	0.45126 (7)	0.004363 (10)	−0.32970 (2)	0.07079 (13)
O1	−0.2183 (5)	0.21731 (10)	0.5145 (2)	0.0585 (7)
N1	−0.1104 (5)	0.19722 (10)	0.4410 (2)	0.0396 (6)
N2	0.1662 (5)	0.12361 (12)	0.1779 (3)	0.0497 (7)
C2	−0.0545 (6)	0.23247 (13)	0.3482 (3)	0.0430 (7)
C3	−0.0005 (7)	0.20025 (14)	0.2456 (3)	0.0446 (8)
C4	0.1610 (7)	0.15434 (14)	0.2874 (3)	0.0436 (8)
C5	0.0622 (7)	0.12052 (14)	0.3706 (3)	0.0465 (8)
C6	0.0205 (6)	0.14798 (13)	0.4821 (3)	0.0437 (8)
C7	0.3460 (7)	0.12450 (15)	0.1413 (3)	0.0483 (8)
C11	0.3692 (6)	0.09610 (14)	0.0320 (3)	0.0448 (8)
C12	0.2093 (8)	0.05855 (17)	−0.0219 (4)	0.0594 (10)
C13	0.2309 (8)	0.03243 (18)	−0.1257 (4)	0.0627 (11)
C14	0.4139 (7)	0.04436 (13)	−0.1744 (3)	0.0477 (8)
C15	0.5738 (8)	0.08174 (18)	−0.1235 (4)	0.0603 (10)
C16	0.5511 (8)	0.10713 (18)	−0.0197 (4)	0.0620 (11)
C21	0.1498 (10)	0.26798 (18)	0.4090 (4)	0.0606 (11)
C22	−0.2755 (9)	0.26510 (18)	0.2949 (4)	0.0619 (11)
C61	0.2487 (8)	0.1601 (2)	0.5784 (4)	0.0597 (10)
C62	−0.1361 (9)	0.11420 (17)	0.5396 (4)	0.0593 (11)
H4	0.311 (6)	0.1664 (14)	0.325 (3)	0.050 (10)*
H7	0.480 (7)	0.1429 (17)	0.184 (3)	0.068 (13)*
H12	0.090 (7)	0.0478 (17)	0.015 (3)	0.070 (13)*
H13	0.134 (9)	0.0048 (16)	−0.153 (4)	0.075 (15)*
H15	0.700 (8)	0.0923 (17)	−0.163 (4)	0.075 (13)*
H16	0.653 (7)	0.1296 (15)	0.018 (3)	0.055 (11)*
H21	0.297 (10)	0.252 (2)	0.444 (4)	0.093 (18)*
H22	0.113 (8)	0.2853 (17)	0.473 (4)	0.073 (13)*
H23	0.159 (8)	0.2939 (19)	0.348 (4)	0.087 (15)*
H24	−0.290 (7)	0.2892 (17)	0.358 (4)	0.072 (13)*
H25	−0.414 (7)	0.2419 (15)	0.257 (3)	0.053 (11)*
H26	−0.265 (8)	0.2852 (18)	0.222 (4)	0.079 (14)*
H31	0.066 (7)	0.2249 (15)	0.193 (3)	0.064 (12)*
H32	−0.150 (7)	0.1885 (14)	0.197 (3)	0.047 (10)*
H51	0.161 (6)	0.0910 (14)	0.400 (3)	0.050 (10)*
H52	−0.098 (7)	0.1051 (14)	0.317 (3)	0.053 (10)*
H61	0.362 (6)	0.1766 (15)	0.550 (3)	0.048 (11)*
H62	0.309 (8)	0.1289 (18)	0.610 (4)	0.076 (14)*
H63	0.220 (8)	0.1847 (19)	0.651 (4)	0.092 (16)*
H64	−0.056 (7)	0.0827 (16)	0.557 (3)	0.055 (11)*
H65	−0.163 (7)	0.1318 (16)	0.608 (4)	0.067 (13)*
H66	−0.287 (8)	0.1113 (16)	0.486 (4)	0.063 (13)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
I1	0.1133 (3)	0.05549 (17)	0.05413 (17)	0.00967 (15)	0.04074 (17)	−0.01044 (11)
O1	0.0764 (19)	0.0600 (16)	0.0539 (15)	0.0096 (14)	0.0431 (14)	−0.0009 (12)
N1	0.0464 (16)	0.0417 (14)	0.0369 (14)	−0.0001 (12)	0.0219 (13)	−0.0020 (11)
N2	0.0523 (18)	0.0571 (18)	0.0444 (16)	0.0030 (15)	0.0209 (14)	−0.0101 (13)
C2	0.053 (2)	0.0433 (17)	0.0383 (16)	−0.0003 (16)	0.0215 (15)	0.0012 (13)
C3	0.049 (2)	0.052 (2)	0.0370 (16)	0.0005 (17)	0.0187 (16)	−0.0035 (14)
C4	0.044 (2)	0.053 (2)	0.0382 (17)	−0.0012 (16)	0.0182 (15)	−0.0080 (14)
C5	0.055 (2)	0.0417 (18)	0.0470 (19)	0.0053 (17)	0.0219 (17)	0.0004 (14)
C6	0.050 (2)	0.0431 (18)	0.0430 (19)	0.0014 (15)	0.0209 (16)	0.0016 (14)
C7	0.054 (2)	0.050 (2)	0.0455 (19)	0.0025 (18)	0.0199 (17)	−0.0053 (15)
C11	0.0465 (19)	0.0495 (19)	0.0405 (18)	0.0077 (16)	0.0151 (15)	−0.0038 (14)
C12	0.061 (3)	0.068 (3)	0.059 (2)	−0.009 (2)	0.034 (2)	−0.0148 (19)
C13	0.069 (3)	0.063 (2)	0.064 (3)	−0.019 (2)	0.032 (2)	−0.021 (2)
C14	0.064 (2)	0.0438 (18)	0.0399 (17)	0.0100 (17)	0.0226 (17)	−0.0028 (14)
C15	0.060 (3)	0.077 (3)	0.053 (2)	−0.008 (2)	0.031 (2)	−0.013 (2)
C16	0.058 (3)	0.078 (3)	0.057 (2)	−0.018 (2)	0.027 (2)	−0.026 (2)
C21	0.082 (3)	0.054 (2)	0.055 (2)	−0.020 (2)	0.036 (2)	−0.0109 (19)
C22	0.083 (3)	0.058 (2)	0.053 (2)	0.020 (2)	0.032 (2)	0.0064 (19)
C61	0.062 (3)	0.067 (3)	0.048 (2)	0.001 (2)	0.011 (2)	0.005 (2)
C62	0.073 (3)	0.051 (2)	0.064 (3)	−0.001 (2)	0.036 (3)	0.008 (2)

Geometric parameters (Å, º)

I1—C14	2.101 (3)	C11—C16	1.379 (5)
O1—N1	1.282 (3)	C12—C13	1.390 (5)
N1—C2	1.492 (4)	C12—H12	0.95 (4)
N1—C6	1.497 (4)	C13—C14	1.368 (5)
N2—C7	1.235 (5)	C13—H13	0.92 (5)
N2—C4	1.479 (4)	C14—C15	1.366 (5)
C2—C21	1.526 (6)	C15—C16	1.383 (5)
C2—C3	1.529 (4)	C15—H15	1.00 (4)
C2—C22	1.535 (6)	C16—H16	0.86 (4)
C3—C4	1.517 (5)	C21—H21	0.95 (5)
C3—H31	1.02 (4)	C21—H22	0.92 (5)
C3—H32	0.96 (4)	C21—H23	0.97 (5)
C4—C5	1.509 (5)	C22—H24	0.97 (4)
C4—H4	0.93 (4)	C22—H25	1.01 (4)
C5—C6	1.523 (5)	C22—H26	0.99 (5)
C5—H51	0.97 (4)	C61—H61	0.91 (4)
C5—H52	1.06 (4)	C61—H62	0.92 (5)
C6—C61	1.524 (6)	C61—H63	1.09 (5)
C6—C62	1.534 (5)	C62—H64	0.94 (4)
C7—C11	1.476 (5)	C62—H65	0.95 (4)
C7—H7	0.94 (4)	C62—H66	0.94 (4)
C11—C12	1.378 (5)
O1···O1^i	5.889 (4)	O1···H61^i	2.81 (4)
O1···O1^ii	5.908 (2)	O1···H21^i	2.89 (6)
O1···C22^ii	3.310 (5)	O1···H26^ii	2.44 (5)
O1···C3^ii	3.356 (5)	O1···H31^ii	2.71 (4)
O1—N1—C2	116.7 (3)	C11—C12—C13	120.8 (4)
O1—N1—C6	116.5 (2)	C11—C12—H12	121 (3)
C2—N1—C6	123.1 (3)	C13—C12—H12	118 (3)
C7—N2—C4	118.7 (3)	C14—C13—C12	119.2 (4)
N1—C2—C21	110.1 (3)	C14—C13—H13	122 (3)
N1—C2—C3	109.3 (3)	C12—C13—H13	118 (3)
C21—C2—C3	111.9 (3)	C15—C14—C13	121.2 (3)
N1—C2—C22	106.9 (3)	C15—C14—I1	119.2 (3)
C21—C2—C22	109.4 (4)	C13—C14—I1	119.6 (3)
C3—C2—C22	109.0 (3)	C14—C15—C16	119.0 (4)
C4—C3—C2	115.3 (3)	C14—C15—H15	121 (2)
C4—C3—H31	111 (2)	C16—C15—H15	120 (3)
C2—C3—H31	107 (2)	C11—C16—C15	121.4 (4)
C4—C3—H32	110 (2)	C11—C16—H16	116 (3)
C2—C3—H32	106 (2)	C15—C16—H16	122 (3)
H31—C3—H32	107 (3)	C2—C21—H21	117 (3)
N2—C4—C5	108.0 (3)	C2—C21—H22	109 (3)
N2—C4—C3	107.9 (3)	H21—C21—H22	105 (4)
C5—C4—C3	109.6 (3)	C2—C21—H23	106 (3)
N2—C4—H4	110 (2)	H21—C21—H23	113 (4)
C5—C4—H4	113 (2)	H22—C21—H23	107 (4)
C3—C4—H4	109 (2)	C2—C22—H24	107 (3)
C4—C5—C6	114.8 (3)	C2—C22—H25	110 (2)
C4—C5—H51	112 (2)	H24—C22—H25	119 (3)
C6—C5—H51	107 (2)	C2—C22—H26	112 (3)
C4—C5—H52	107.3 (19)	H24—C22—H26	108 (3)
C6—C5—H52	109.5 (19)	H25—C22—H26	100 (3)
H51—C5—H52	106 (3)	C6—C61—H61	116 (2)
N1—C6—C5	108.8 (3)	C6—C61—H62	106 (3)
N1—C6—C61	109.4 (3)	H61—C61—H62	108 (4)
C5—C6—C61	112.6 (3)	C6—C61—H63	112 (3)
N1—C6—C62	107.3 (3)	H61—C61—H63	105 (3)
C5—C6—C62	109.4 (3)	H62—C61—H63	110 (4)
C61—C6—C62	109.2 (3)	C6—C62—H64	105 (2)
N2—C7—C11	123.3 (4)	C6—C62—H65	109 (3)
N2—C7—H7	121 (2)	H64—C62—H65	115 (3)
C11—C7—H7	115 (2)	C6—C62—H66	110 (3)
C12—C11—C16	118.4 (3)	H64—C62—H66	114 (4)
C12—C11—C7	121.2 (3)	H65—C62—H66	104 (4)
C16—C11—C7	120.4 (4)
O1—N1—C2—C21	74.5 (4)	O1—N1—C6—C62	42.1 (4)
C6—N1—C2—C21	−83.0 (4)	C2—N1—C6—C62	−160.4 (3)
O1—N1—C2—C3	−162.1 (3)	C4—C5—C6—N1	48.5 (4)
C6—N1—C2—C3	40.4 (4)	C4—C5—C6—C61	−72.9 (4)
O1—N1—C2—C22	−44.3 (4)	C4—C5—C6—C62	165.5 (3)
C6—N1—C2—C22	158.3 (3)	C4—N2—C7—C11	−178.9 (3)
N1—C2—C3—C4	−45.0 (4)	N2—C7—C11—C12	−13.3 (6)
C21—C2—C3—C4	77.3 (4)	N2—C7—C11—C16	165.9 (4)
C22—C2—C3—C4	−161.5 (3)	C16—C11—C12—C13	0.0 (7)
C7—N2—C4—C5	−133.8 (4)	C7—C11—C12—C13	179.2 (4)
C7—N2—C4—C3	107.8 (4)	C11—C12—C13—C14	0.1 (7)
C2—C3—C4—N2	172.0 (3)	C12—C13—C14—C15	−0.6 (7)
C2—C3—C4—C5	54.6 (4)	C12—C13—C14—I1	179.1 (3)
N2—C4—C5—C6	−173.9 (3)	C13—C14—C15—C16	1.1 (7)
C3—C4—C5—C6	−56.6 (4)	I1—C14—C15—C16	−178.6 (3)
O1—N1—C6—C5	160.4 (3)	C12—C11—C16—C15	0.5 (7)
C2—N1—C6—C5	−42.1 (4)	C7—C11—C16—C15	−178.7 (4)
O1—N1—C6—C61	−76.2 (4)	C14—C15—C16—C11	−1.0 (7)
C2—N1—C6—C61	81.3 (4)

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

(4b) 4-(4-iodophenyl)methyleneamino-2,2,6,6-tetramethylpiperidin-1-oxyl

Crystal data

C16H22IN2O	F(000) = 1544.00
Mr = 385.27	Dx = 1.476 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 10.980 (4) Å	Cell parameters from 25 reflections
b = 38.914 (4) Å	θ = 17.0–17.5°
c = 8.358 (4) Å	µ = 1.85 mm^−1
β = 103.88 (3)°	T = 295 K
V = 3466 (1) Å^3	Prism, orange
Z = 8	0.30 × 0.27 × 0.15 mm

Data collection

Rigaku AFC7R diffractometer	5046 reflections with I > 2σ(I)
Radiation source: Rigaku rotating anode	Rint = 0.022
Graphite monochromator	θmax = 27.5°, θmin = 2.1°
ω–2θ scans	h = −14→13
Absorption correction: ψ scans(north,Phillips & Mathews,1968) ?	k = −50→0
Tmin = 0.828, Tmax = 0.999	l = 0→10
8478 measured reflections	3 standard reflections every 150 reflections
7950 independent reflections	intensity decay: −4.1%

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.037	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.107	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	Calculated w = 1/[σ^2(Fo^2) + (0.0333P)^2 + 3.3418P] where P = (Fo^2 + 2Fc^2)/3
7950 reflections	(Δ/σ)max = 0.004
441 parameters	Δρmax = 0.39 e Å^−3
0 restraints	Δρmin = −0.36 e Å^−3

Special details

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

Refinement. Refinement 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 (Ų)

	x	y	z	Uiso*/Ueq
I1A	1.07330 (3)	0.188609 (8)	−0.17483 (4)	0.06813 (11)
O1A	0.2750 (3)	0.16431 (10)	0.6753 (4)	0.0859 (11)
N1A	0.3581 (3)	0.17027 (9)	0.5950 (4)	0.0582 (9)
N2A	0.6328 (4)	0.18288 (9)	0.3200 (5)	0.0643 (10)
C2A	0.3137 (4)	0.18603 (12)	0.4301 (6)	0.0621 (11)
C3A	0.4137 (5)	0.18174 (15)	0.3346 (7)	0.0637 (12)
C4A	0.5473 (4)	0.19049 (12)	0.4285 (6)	0.0613 (11)
C5A	0.5791 (4)	0.16798 (13)	0.5798 (7)	0.0619 (12)
C6A	0.4911 (4)	0.17099 (12)	0.6956 (6)	0.0609 (11)
C7A	0.6988 (5)	0.20582 (14)	0.2923 (6)	0.0609 (12)
C11A	0.7877 (4)	0.20194 (11)	0.1866 (5)	0.0525 (9)
C12A	0.8089 (4)	0.16985 (11)	0.1240 (6)	0.0595 (11)
C13A	0.8872 (4)	0.16612 (11)	0.0185 (6)	0.0581 (10)
C14A	0.9484 (4)	0.19496 (11)	−0.0216 (5)	0.0554 (10)
C15A	0.9309 (5)	0.22697 (12)	0.0408 (6)	0.0589 (11)
C16A	0.8507 (4)	0.23044 (12)	0.1434 (6)	0.0588 (11)
C21A	0.2818 (6)	0.22373 (15)	0.4509 (8)	0.0918 (18)
C22A	0.1961 (5)	0.16612 (18)	0.3428 (7)	0.0934 (18)
C61A	0.5130 (6)	0.20386 (15)	0.7975 (7)	0.0906 (17)
C62A	0.5095 (5)	0.13973 (15)	0.8101 (7)	0.0827 (15)
I1B	0.73229 (3)	0.063140 (8)	0.04373 (4)	0.07281 (11)
O1B	−0.0794 (3)	0.08687 (10)	0.8680 (5)	0.0879 (11)
N1B	0.0055 (3)	0.08162 (9)	0.7883 (5)	0.0584 (9)
N2B	0.2829 (4)	0.06509 (10)	0.5236 (6)	0.0712 (11)
C2B	0.1309 (5)	0.06987 (11)	0.8887 (6)	0.0650 (12)
C3B	0.2267 (4)	0.07301 (13)	0.7885 (7)	0.0662 (12)
C4B	0.1847 (4)	0.05903 (12)	0.6126 (7)	0.0661 (12)
C5B	0.0688 (5)	0.07902 (14)	0.5272 (7)	0.0673 (12)
C6B	−0.0401 (4)	0.07675 (12)	0.6080 (6)	0.0624 (11)
C7B	0.3240 (4)	0.04092 (13)	0.4585 (6)	0.0622 (11)
C11B	0.4205 (4)	0.04540 (11)	0.3647 (6)	0.0566 (10)
C12B	0.4691 (4)	0.07771 (12)	0.3499 (6)	0.0640 (12)
C13B	0.5574 (4)	0.08276 (13)	0.2593 (7)	0.0646 (12)
C14B	0.5987 (4)	0.05483 (11)	0.1824 (5)	0.0580 (10)
C15B	0.5514 (5)	0.02231 (12)	0.1987 (6)	0.0642 (12)
C16B	0.4638 (5)	0.01787 (12)	0.2890 (6)	0.0634 (12)
C21B	0.1176 (6)	0.03273 (14)	0.9472 (8)	0.0942 (18)
C22B	0.1651 (6)	0.09340 (15)	1.0399 (7)	0.0870 (16)
C61B	−0.1091 (5)	0.04208 (14)	0.5752 (8)	0.0871 (17)
C62B	−0.1329 (5)	0.10603 (15)	0.5407 (8)	0.0918 (17)
H4A	0.551 (4)	0.2172 (10)	0.455 (5)	0.055 (11)*
H7A	0.692 (4)	0.2214 (10)	0.324 (5)	0.033 (12)*
H12A	0.761 (4)	0.1478 (11)	0.154 (5)	0.063 (12)*
H13A	0.908 (3)	0.1415 (10)	−0.020 (5)	0.053 (11)*
H15A	0.969 (4)	0.2443 (13)	0.022 (6)	0.077 (16)*
H16A	0.840 (3)	0.2513 (10)	0.179 (5)	0.044 (11)*
H21A	0.2155	0.2252	0.5040	0.110*
H22A	0.3537	0.2352	0.5126	0.110*
H23A	0.2567	0.2340	0.3438	0.110*
H24A	0.1332	0.1680	0.4038	0.111*
H25A	0.1649	0.1743	0.2350	0.111*
H26A	0.2167	0.1421	0.3380	0.111*
H31A	0.400 (4)	0.1958 (11)	0.255 (6)	0.062 (14)*
H32A	0.420 (4)	0.1600 (13)	0.309 (6)	0.071 (15)*
H51A	0.658 (5)	0.1743 (13)	0.617 (6)	0.086 (17)*
H52A	0.576 (4)	0.1430 (13)	0.544 (6)	0.073 (14)*
H61A	0.5103	0.2229	0.7266	0.109*
H62A	0.5951	0.2027	0.8711	0.109*
H63A	0.4524	0.2059	0.8591	0.109*
H64A	0.5941	0.1382	0.8671	0.100*
H65A	0.4581	0.1427	0.8871	0.100*
H66A	0.4837	0.1198	0.7470	0.100*
H4B	0.168 (4)	0.0325 (10)	0.614 (5)	0.055 (11)*
H7B	0.295 (4)	0.0180 (12)	0.474 (5)	0.072 (14)*
H12B	0.441 (4)	0.0976 (12)	0.409 (6)	0.082 (15)*
H13B	0.586 (4)	0.1038 (11)	0.261 (5)	0.063 (13)*
H15B	0.577 (5)	0.0068 (13)	0.144 (6)	0.085 (17)*
H16B	0.428 (4)	−0.0022 (12)	0.294 (5)	0.066 (14)*
H21B	0.2020	0.0260	1.0100	0.125*
H22B	0.1032	0.0163	0.8629	0.078*
H23B	0.0571	0.0347	1.0205	0.106*
H24B	0.1053	0.0887	1.0984	0.109*
H25B	0.1643	0.1174	1.0140	0.082*
H26B	0.2383	0.0855	1.1005	0.108*
H31B	0.306 (4)	0.0592 (11)	0.850 (5)	0.070 (13)*
H32B	0.246 (4)	0.0996 (11)	0.772 (5)	0.054 (11)*
H51B	0.089 (4)	0.1034 (13)	0.533 (6)	0.080 (15)*
H52B	0.027 (5)	0.0713 (14)	0.413 (7)	0.104 (19)*
H61B	−0.1744	0.0425	0.6509	0.127*
H62B	−0.0534	0.0215	0.5951	0.081*
H63B	−0.1456	0.0369	0.4885	0.147*
H64B	−0.1761	0.0987	0.4305	0.100*
H65B	−0.0853	0.1266	0.5670	0.081*
H66B	−0.1867	0.1030	0.5787	0.085*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
I1A	0.0758 (2)	0.06366 (18)	0.0767 (2)	0.00126 (15)	0.04144 (17)	0.00330 (15)
O1A	0.075 (2)	0.114 (3)	0.083 (2)	0.011 (2)	0.048 (2)	0.016 (2)
N1A	0.056 (2)	0.063 (2)	0.061 (2)	0.0034 (17)	0.0226 (18)	0.0026 (18)
N2A	0.059 (2)	0.056 (2)	0.087 (3)	−0.0022 (18)	0.038 (2)	−0.013 (2)
C2A	0.056 (2)	0.066 (3)	0.067 (3)	0.011 (2)	0.020 (2)	0.009 (2)
C3A	0.068 (3)	0.064 (3)	0.065 (3)	0.008 (2)	0.026 (2)	0.007 (3)
C4A	0.060 (3)	0.056 (3)	0.076 (3)	−0.001 (2)	0.032 (2)	−0.003 (2)
C5A	0.048 (3)	0.058 (3)	0.081 (3)	−0.001 (2)	0.019 (2)	−0.006 (2)
C6A	0.056 (3)	0.061 (3)	0.065 (3)	0.000 (2)	0.013 (2)	−0.002 (2)
C7A	0.065 (3)	0.060 (3)	0.062 (3)	0.011 (2)	0.024 (2)	−0.006 (2)
C11A	0.049 (2)	0.058 (2)	0.053 (2)	−0.0031 (18)	0.0161 (19)	0.0016 (19)
C12A	0.055 (2)	0.051 (2)	0.077 (3)	−0.002 (2)	0.025 (2)	−0.002 (2)
C13A	0.056 (2)	0.052 (2)	0.072 (3)	0.004 (2)	0.026 (2)	0.000 (2)
C14A	0.050 (2)	0.064 (3)	0.055 (2)	0.0012 (19)	0.0186 (19)	0.000 (2)
C15A	0.071 (3)	0.053 (2)	0.058 (3)	−0.007 (2)	0.027 (2)	−0.001 (2)
C16A	0.067 (3)	0.053 (2)	0.061 (3)	−0.004 (2)	0.025 (2)	−0.008 (2)
C21A	0.091 (4)	0.083 (4)	0.115 (5)	0.029 (3)	0.051 (4)	0.022 (3)
C22A	0.057 (3)	0.141 (5)	0.078 (4)	−0.005 (3)	0.007 (3)	0.016 (4)
C61A	0.107 (4)	0.089 (4)	0.073 (4)	−0.007 (3)	0.016 (3)	−0.023 (3)
C62A	0.076 (3)	0.086 (4)	0.081 (4)	0.001 (3)	0.009 (3)	0.018 (3)
I1B	0.0777 (2)	0.0713 (2)	0.0810 (2)	0.01183 (17)	0.04175 (18)	0.00308 (17)
O1B	0.085 (2)	0.091 (3)	0.106 (3)	−0.004 (2)	0.057 (2)	−0.016 (2)
N1B	0.061 (2)	0.052 (2)	0.070 (2)	−0.0033 (16)	0.0305 (19)	−0.0060 (18)
N2B	0.064 (2)	0.059 (2)	0.105 (3)	−0.0060 (19)	0.048 (2)	−0.002 (2)
C2B	0.080 (3)	0.051 (2)	0.067 (3)	0.006 (2)	0.023 (3)	0.007 (2)
C3B	0.052 (3)	0.066 (3)	0.082 (3)	0.004 (2)	0.018 (2)	−0.001 (3)
C4B	0.067 (3)	0.055 (3)	0.088 (3)	−0.009 (2)	0.040 (3)	−0.007 (2)
C5B	0.068 (3)	0.069 (3)	0.067 (3)	−0.003 (3)	0.020 (3)	−0.002 (3)
C6B	0.054 (3)	0.060 (3)	0.074 (3)	−0.003 (2)	0.019 (2)	−0.009 (2)
C7B	0.060 (3)	0.059 (3)	0.070 (3)	−0.005 (2)	0.021 (2)	−0.002 (2)
C11B	0.050 (2)	0.057 (2)	0.065 (3)	0.0003 (19)	0.017 (2)	−0.007 (2)
C12B	0.053 (2)	0.057 (3)	0.087 (3)	−0.002 (2)	0.026 (2)	−0.018 (2)
C13B	0.057 (3)	0.056 (3)	0.086 (3)	0.000 (2)	0.027 (2)	−0.008 (2)
C14B	0.054 (2)	0.063 (3)	0.060 (3)	0.010 (2)	0.020 (2)	0.003 (2)
C15B	0.072 (3)	0.058 (3)	0.068 (3)	0.013 (2)	0.027 (2)	−0.007 (2)
C16B	0.071 (3)	0.052 (3)	0.072 (3)	0.000 (2)	0.027 (2)	0.001 (2)
C21B	0.128 (5)	0.062 (3)	0.101 (4)	0.010 (3)	0.044 (4)	0.019 (3)
C22B	0.112 (5)	0.081 (4)	0.063 (3)	0.006 (3)	0.011 (3)	0.001 (3)
C61B	0.078 (3)	0.078 (3)	0.111 (5)	−0.023 (3)	0.034 (3)	−0.031 (3)
C62B	0.068 (3)	0.090 (4)	0.109 (5)	0.009 (3)	0.004 (3)	−0.010 (3)

Geometric parameters (Å, º)

I1A—C14A	2.103 (4)	I1B—C14B	2.101 (4)
O1A—N1A	1.277 (4)	O1B—N1B	1.286 (4)
N1A—C2A	1.480 (6)	N1B—C6B	1.482 (6)
N1A—C6A	1.500 (6)	N1B—C2B	1.501 (6)
N2A—C7A	1.206 (6)	N2B—C7B	1.225 (6)
N2A—C4A	1.484 (5)	N2B—C4B	1.468 (6)
C2A—C3A	1.514 (6)	C2B—C3B	1.499 (7)
C2A—C21A	1.527 (7)	C2B—C22B	1.532 (7)
C2A—C22A	1.533 (7)	C2B—C21B	1.543 (7)
C3A—C4A	1.526 (7)	C3B—C4B	1.531 (7)
C3A—H31A	0.85 (5)	C3B—H31B	1.05 (4)
C3A—H32A	0.88 (5)	C3B—H32B	1.07 (4)
C4A—C5A	1.509 (7)	C4B—C5B	1.516 (7)
C4A—H4A	1.06 (4)	C4B—H4B	1.05 (4)
C5A—C6A	1.527 (6)	C5B—C6B	1.510 (6)
C5A—H51A	0.88 (5)	C5B—H51B	0.97 (5)
C5A—H52A	1.02 (5)	C5B—H52B	1.00 (6)
C6A—C61A	1.523 (7)	C6B—C61B	1.539 (7)
C6A—C62A	1.530 (7)	C6B—C62B	1.542 (7)
C7A—C11A	1.473 (6)	C7B—C11B	1.472 (6)
C7A—H7A	0.67 (4)	C7B—H7B	0.97 (5)
C11A—C12A	1.395 (6)	C11B—C12B	1.383 (6)
C11A—C16A	1.400 (6)	C11B—C16B	1.385 (6)
C12A—C13A	1.379 (6)	C12B—C13B	1.380 (6)
C12A—H12A	1.07 (4)	C12B—H12B	1.01 (5)
C13A—C14A	1.390 (6)	C13B—C14B	1.393 (6)
C13A—H13A	1.05 (4)	C13B—H13B	0.88 (4)
C14A—C15A	1.382 (6)	C14B—C15B	1.387 (6)
C15A—C16A	1.375 (6)	C15B—C16B	1.369 (7)
C15A—H15A	0.83 (5)	C15B—H15B	0.84 (5)
C16A—H16A	0.88 (4)	C16B—H16B	0.88 (4)
C21A—H21A	0.942 (5)	C21B—H21B	0.984 (7)
C21A—H22A	0.945 (7)	C21B—H22B	0.937 (6)
C21A—H23A	0.959 (6)	C21B—H23B	1.009 (6)
C22A—H24A	0.955 (6)	C22B—H24B	0.927 (6)
C22A—H25A	0.940 (6)	C22B—H25B	0.958 (6)
C22A—H26A	0.966 (7)	C22B—H26B	0.895 (6)
C61A—H61A	0.946 (6)	C61B—H61B	1.064 (6)
C61A—H62A	0.964 (6)	C61B—H62B	0.998 (6)
C61A—H63A	0.937 (6)	C61B—H63B	0.766 (6)
C62A—H64A	0.938 (5)	C62B—H64B	0.973 (6)
C62A—H65A	0.960 (6)	C62B—H65B	0.952 (6)
C62A—H66A	0.943 (6)	C62B—H66B	0.745 (6)
I1A···O1A^i	2.949 (3)	O1B···H13A^ii	2.34 (4)
I1B···O1B^i	2.957 (4)	O1A···O1B	5.461 (5)
O1B···C13A^ii	3.384 (6)
O1A—N1A—C2A	116.5 (3)	H65A—C62A—H66A	109.2 (5)
O1A—N1A—C6A	115.6 (4)	O1B—N1B—C6B	115.9 (4)
C2A—N1A—C6A	125.0 (3)	O1B—N1B—C2B	116.1 (4)
C7A—N2A—C4A	117.8 (4)	C6B—N1B—C2B	124.8 (3)
N1A—C2A—C3A	109.1 (4)	C4B—N2B—C7B	119.6 (4)
N1A—C2A—C21A	109.0 (4)	C3B—C2B—N1B	109.5 (4)
C3A—C2A—C21A	112.4 (4)	C3B—C2B—C22B	110.2 (4)
N1A—C2A—C22A	106.6 (4)	N1B—C2B—C22B	106.8 (4)
C3A—C2A—C22A	109.2 (4)	C3B—C2B—C21B	112.7 (4)
C21A—C2A—C22A	110.5 (4)	N1B—C2B—C21B	108.6 (4)
C2A—C3A—C4A	115.7 (4)	C22B—C2B—C21B	108.8 (4)
N2A—C4A—C5A	110.0 (4)	C2B—C3B—C4B	114.7 (4)
N2A—C4A—C3A	108.2 (4)	N2B—C4B—C5B	108.4 (4)
C5A—C4A—C3A	107.6 (4)	N2B—C4B—C3B	109.9 (4)
C4A—C5A—C6A	115.6 (4)	C5B—C4B—C3B	107.1 (4)
N1A—C6A—C61A	109.3 (4)	C6B—C5B—C4B	115.2 (4)
N1A—C6A—C5A	108.8 (4)	N1B—C6B—C5B	109.7 (4)
C61A—C6A—C5A	112.3 (4)	N1B—C6B—C61B	109.0 (4)
N1A—C6A—C62A	107.5 (4)	C5B—C6B—C61B	112.4 (4)
C61A—C6A—C62A	109.8 (4)	N1B—C6B—C62B	108.0 (4)
C5A—C6A—C62A	109.1 (4)	C5B—C6B—C62B	108.6 (4)
N2A—C7A—C11A	123.6 (5)	C61B—C6B—C62B	109.2 (4)
C12A—C11A—C16A	118.4 (4)	N2B—C7B—C11B	122.3 (4)
C12A—C11A—C7A	120.7 (4)	C11B—C7B—H7B	119 (3)
C16A—C11A—C7A	120.9 (4)	C12B—C11B—C16B	118.7 (4)
C13A—C12A—C11A	121.3 (4)	C12B—C11B—C7B	119.8 (4)
C12A—C13A—C14A	118.8 (4)	C16B—C11B—C7B	121.4 (4)
C15A—C14A—C13A	121.2 (4)	C13B—C12B—C11B	121.0 (4)
C15A—C14A—I1A	120.4 (3)	C12B—C13B—C14B	119.4 (4)
C13A—C14A—I1A	118.4 (3)	C15B—C14B—C13B	119.7 (4)
C16A—C15A—C14A	119.5 (4)	C15B—C14B—I1B	121.5 (3)
C15A—C16A—C11A	120.9 (4)	C13B—C14B—I1B	118.8 (3)
C2A—C3A—H31A	109 (3)	C16B—C15B—C14B	119.9 (4)
C4A—C3A—H31A	103 (3)	C15B—C16B—C11B	121.2 (4)
C2A—C3A—H32A	110 (3)	C2B—C3B—H31B	107 (2)
C4A—C3A—H32A	102 (3)	C4B—C3B—H31B	108 (2)
H31A—C3A—H32A	116 (4)	C2B—C3B—H32B	110 (2)
N2A—C4A—H4A	109 (2)	C4B—C3B—H32B	104 (2)
C5A—C4A—H4A	114 (2)	H31B—C3B—H32B	113 (3)
C3A—C4A—H4A	108 (2)	N2B—C4B—H4B	108 (2)
C4A—C5A—H51A	98 (3)	C5B—C4B—H4B	112 (2)
C6A—C5A—H51A	118 (3)	C3B—C4B—H4B	111 (2)
C4A—C5A—H52A	109 (3)	C6B—C5B—H51B	103 (3)
C6A—C5A—H52A	106 (3)	C4B—C5B—H51B	109 (3)
H51A—C5A—H52A	109 (4)	C6B—C5B—H52B	100 (3)
H51B—C5B—H52B	113 (4)	C4B—C5B—H52B	116 (3)
N2A—C7A—H7A	118 (4)	N2B—C7B—H7B	119 (3)
C11A—C7A—H7A	118 (4)	C13B—C12B—H12B	120 (3)
C13A—C12A—H12A	119 (2)	C11B—C12B—H12B	119 (3)
C11A—C12A—H12A	120 (2)	C12B—C13B—H13B	115 (3)
C12A—C13A—H13A	120 (2)	C14B—C13B—H13B	125 (3)
C14A—C13A—H13A	121 (2)	C16B—C15B—H15B	125 (4)
C16A—C15A—H15A	118 (3)	C14B—C15B—H15B	115 (4)
C14A—C15A—H15A	123 (3)	C15B—C16B—H16B	121 (3)
C15A—C16A—H16A	117 (2)	C11B—C16B—H16B	117 (3)
C11A—C16A—H16A	122 (2)	C2B—C21B—H21B	105.7 (5)
C2A—C21A—H21A	109.6 (5)	C2B—C21B—H22B	114.4 (5)
C2A—C21A—H22A	109.4 (5)	H21B—C21B—H22B	100.7 (5)
H21A—C21A—H22A	110.7 (6)	C2B—C21B—H23B	104.2 (5)
C2A—C21A—H23A	108.5 (5)	H21B—C21B—H23B	111.7 (6)
H21A—C21A—H23A	109.5 (6)	H22B—C21B—H23B	119.5 (7)
H22A—C21A—H23A	109.2 (6)	C2B—C22B—H24B	104.6 (5)
C2A—C22A—H24A	109.9 (6)	C2B—C22B—H25B	114.1 (5)
C2A—C22A—H25A	110.8 (5)	H24B—C22B—H25B	110.1 (6)
H24A—C22A—H25A	110.0 (5)	C2B—C22B—H26B	105.7 (5)
C2A—C22A—H26A	109.3 (5)	H24B—C22B—H26B	106.7 (5)
H24A—C22A—H26A	107.8 (6)	H25B—C22B—H26B	114.8 (6)
H25A—C22A—H26A	109.0 (6)	C6B—C61B—H61B	104.6 (4)
C6A—C61A—H61A	109.4 (5)	C6B—C61B—H62B	114.8 (5)
C6A—C61A—H62A	108.4 (5)	H61B—C61B—H62B	112.8 (6)
H61A—C61A—H62A	108.6 (6)	C6B—C61B—H63B	121.5 (7)
C6A—C61A—H63A	110.0 (5)	H61B—C61B—H63B	106.9 (6)
H61A—C61A—H63A	110.9 (6)	H62B—C61B—H63B	96.1 (5)
H62A—C61A—H63A	109.4 (6)	C6B—C62B—H64B	104.9 (5)
C6A—C62A—H64A	109.5 (5)	C6B—C62B—H65B	105.0 (5)
C6A—C62A—H65A	108.2 (5)	H64B—C62B—H65B	125.6 (7)
H64A—C62A—H65A	109.6 (6)	C6B—C62B—H66B	104.5 (6)
C6A—C62A—H66A	109.2 (5)	H64B—C62B—H66B	95.7 (6)
H64A—C62A—H66A	111.1 (6)	H65B—C62B—H66B	118.9 (7)
O1A—N1A—C2A—C3A	−163.6 (4)	C12A—C11A—C16A—C15A	0.5 (7)
C6A—N1A—C2A—C3A	36.7 (6)	C7A—C11A—C16A—C15A	−178.1 (5)
O1A—N1A—C2A—C21A	73.3 (5)	O1B—N1B—C2B—C3B	−166.5 (4)
C6A—N1A—C2A—C21A	−86.4 (5)	C6B—N1B—C2B—C3B	34.5 (5)
O1A—N1A—C2A—C22A	−45.9 (5)	O1B—N1B—C2B—C22B	−47.1 (5)
C6A—N1A—C2A—C22A	154.4 (4)	C6B—N1B—C2B—C22B	153.9 (4)
N1A—C2A—C3A—C4A	−46.3 (6)	O1B—N1B—C2B—C21B	70.0 (5)
C21A—C2A—C3A—C4A	74.7 (6)	C6B—N1B—C2B—C21B	−88.9 (5)
C22A—C2A—C3A—C4A	−162.4 (5)	N1B—C2B—C3B—C4B	−46.2 (5)
C7A—N2A—C4A—C5A	−118.9 (5)	C22B—C2B—C3B—C4B	−163.5 (4)
C7A—N2A—C4A—C3A	123.8 (5)	C21B—C2B—C3B—C4B	74.8 (6)
C2A—C3A—C4A—N2A	176.7 (4)	C7B—N2B—C4B—C5B	−117.9 (5)
C2A—C3A—C4A—C5A	57.9 (5)	C7B—N2B—C4B—C3B	125.3 (5)
N2A—C4A—C5A—C6A	−175.1 (4)	C2B—C3B—C4B—N2B	177.0 (4)
C3A—C4A—C5A—C6A	−57.4 (5)	C2B—C3B—C4B—C5B	59.5 (5)
N2B—C4B—C5B—C6B	−177.6 (4)	O1B—N1B—C6B—C5B	167.1 (4)
C3B—C4B—C5B—C6B	−59.0 (5)	C2B—N1B—C6B—C5B	−33.9 (6)
O1A—N1A—C6A—C61A	−73.1 (5)	O1B—N1B—C6B—C61B	−69.5 (5)
C2A—N1A—C6A—C61A	86.7 (5)	C2B—N1B—C6B—C61B	89.5 (5)
O1A—N1A—C6A—C5A	163.9 (4)	O1B—N1B—C6B—C62B	49.0 (5)
C2A—N1A—C6A—C5A	−36.2 (6)	C2B—N1B—C6B—C62B	−152.0 (4)
O1A—N1A—C6A—C62A	45.9 (5)	C4B—C5B—C6B—N1B	45.6 (6)
C2A—N1A—C6A—C62A	−154.2 (4)	C4B—C5B—C6B—C61B	−75.8 (6)
C4A—C5A—C6A—N1A	45.7 (5)	C4B—C5B—C6B—C62B	163.3 (4)
C4A—C5A—C6A—C61A	−75.5 (6)	C4B—N2B—C7B—C11B	178.7 (4)
C4A—C5A—C6A—C62A	162.6 (4)	N2B—C7B—C11B—C12B	0.9 (8)
C4A—N2A—C7A—C11A	−179.8 (4)	N2B—C7B—C11B—C16B	−178.6 (5)
N2A—C7A—C11A—C12A	−6.2 (8)	C16B—C11B—C12B—C13B	1.2 (8)
N2A—C7A—C11A—C16A	172.4 (5)	C7B—C11B—C12B—C13B	−178.3 (5)
C16A—C11A—C12A—C13A	−1.8 (7)	C11B—C12B—C13B—C14B	−0.4 (8)
C7A—C11A—C12A—C13A	176.8 (4)	C12B—C13B—C14B—C15B	−0.4 (8)
C11A—C12A—C13A—C14A	1.8 (7)	C12B—C13B—C14B—I1B	179.6 (4)
C12A—C13A—C14A—C15A	−0.6 (7)	C13B—C14B—C15B—C16B	0.5 (8)
C12A—C13A—C14A—I1A	177.5 (3)	I1B—C14B—C15B—C16B	−179.5 (4)
C13A—C14A—C15A—C16A	−0.6 (7)	C14B—C15B—C16B—C11B	0.3 (8)
I1A—C14A—C15A—C16A	−178.7 (4)	C12B—C11B—C16B—C15B	−1.1 (8)
C14A—C15A—C16A—C11A	0.6 (7)	C7B—C11B—C16B—C15B	178.4 (5)

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

(5) 4-(biphenyl-4-yl)methyleneamino-2,2,6,6-tetramethylpiperidin-1-oxyl

Crystal data

C22H27N2O	F(000) = 724.00
Mr = 335.47	Dx = 1.163 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 5.955 (1) Å	Cell parameters from 25 reflections
b = 28.488 (5) Å	θ = 13.9–17.5°
c = 11.796 (2) Å	µ = 0.07 mm^−1
β = 106.72 (2)°	T = 296 K
V = 1916.5 (6) Å^3	Prism, orange
Z = 4	0.45 × 0.35 × 0.30 mm

Data collection

Rigaku AFC5R diffractometer	Rint = 0.033
Radiation source: Rigaku rotating anode	θmax = 27.5°, θmin = 2.8°
Graphite monochromator	h = 0→7
ω scans	k = 0→36
4774 measured reflections	l = −15→14
4372 independent reflections	3 standard reflections every 100 reflections
2488 reflections with I > 2σ(I)	intensity decay: −0.7%

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.062	All H-atom parameters refined
wR(F^2) = 0.182	Calculated w = 1/[σ^2(Fo^2) + (0.0691P)^2 + 0.8294P] where P = (Fo^2 + 2Fc^2)/3
S = 0.98	(Δ/σ)max = 0.194
4372 reflections	Δρmax = 0.29 e Å^−3
335 parameters	Δρmin = −0.25 e Å^−3
0 restraints	Extinction correction: SHELXL, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.013 (2)

Special details

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

Refinement. Refinement 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 (Ų)

	x	y	z	Uiso*/Ueq
O1	−0.2026 (3)	0.22330 (7)	0.61910 (15)	0.0714 (6)
N1	−0.0943 (3)	0.20482 (7)	0.55047 (15)	0.0492 (5)
N2	0.1857 (4)	0.13859 (8)	0.30386 (17)	0.0607 (6)
C2	−0.0380 (4)	0.23685 (8)	0.46225 (19)	0.0526 (6)
C3	0.0168 (5)	0.20741 (9)	0.3655 (2)	0.0536 (6)
C4	0.1819 (4)	0.16641 (8)	0.4082 (2)	0.0516 (6)
C5	0.0833 (5)	0.13554 (9)	0.4874 (2)	0.0569 (6)
C6	0.0346 (4)	0.16040 (8)	0.59225 (19)	0.0522 (6)
C7	0.3585 (5)	0.13943 (9)	0.2654 (2)	0.0568 (6)
C11	0.3634 (4)	0.11384 (8)	0.1576 (2)	0.0518 (6)
C12	0.1862 (6)	0.08486 (13)	0.1029 (3)	0.0941 (12)
C13	0.1850 (7)	0.06131 (14)	0.0009 (3)	0.1019 (13)
C14	0.3603 (4)	0.06534 (8)	−0.05117 (19)	0.0517 (6)
C15	0.5345 (6)	0.09551 (16)	0.0024 (3)	0.1100 (15)
C16	0.5377 (6)	0.11921 (17)	0.1053 (3)	0.1160 (17)
C21	0.1670 (6)	0.26881 (11)	0.5243 (3)	0.0734 (9)
C22	−0.2572 (7)	0.26630 (13)	0.4070 (3)	0.0764 (9)
C41	0.3546 (5)	0.03879 (8)	−0.1609 (2)	0.0564 (6)
C42	0.1828 (7)	0.00671 (14)	−0.2074 (3)	0.1034 (13)
C43	0.1731 (9)	−0.01843 (17)	−0.3096 (4)	0.1279 (18)
C44	0.3387 (8)	−0.01204 (14)	−0.3654 (3)	0.0967 (12)
C45	0.5088 (8)	0.02003 (15)	−0.3224 (3)	0.0996 (12)
C46	0.5178 (6)	0.04565 (12)	−0.2207 (3)	0.0829 (9)
C61	0.2610 (6)	0.17127 (14)	0.6900 (3)	0.0719 (8)
C62	−0.1236 (7)	0.12947 (12)	0.6428 (3)	0.0755 (8)
H4	0.344 (4)	0.1780 (8)	0.4514 (19)	0.050 (6)*
H7	0.495 (5)	0.1584 (10)	0.306 (3)	0.088 (9)*
H12	0.060 (7)	0.0831 (14)	0.135 (3)	0.138 (14)*
H13	0.070 (7)	0.0412 (15)	−0.023 (4)	0.136 (15)*
H15	0.644 (7)	0.1022 (14)	−0.036 (3)	0.132 (14)*
H16	0.644 (7)	0.1408 (15)	0.133 (4)	0.140 (15)*
H21	0.322 (5)	0.2500 (11)	0.553 (3)	0.087 (10)*
H22	0.139 (5)	0.2830 (11)	0.593 (3)	0.095 (10)*
H23	0.181 (5)	0.2931 (11)	0.466 (3)	0.090 (9)*
H24	−0.282 (5)	0.2879 (11)	0.468 (3)	0.089 (9)*
H25	−0.406 (6)	0.2459 (13)	0.374 (3)	0.109 (12)*
H26	−0.237 (5)	0.2841 (11)	0.342 (3)	0.098 (10)*
H31	0.082 (5)	0.2276 (9)	0.316 (2)	0.070 (8)*
H32	−0.130 (5)	0.1947 (9)	0.312 (2)	0.067 (7)*
H42	0.072 (7)	0.0027 (14)	−0.174 (3)	0.122 (14)*
H43	0.063 (9)	−0.0409 (17)	−0.332 (4)	0.17 (2)*
H44	0.323 (7)	−0.0274 (14)	−0.434 (4)	0.127 (14)*
H45	0.634 (8)	0.0267 (14)	−0.361 (4)	0.142 (15)*
H46	0.650 (6)	0.0680 (13)	−0.189 (3)	0.115 (12)*
H51	0.186 (5)	0.1099 (10)	0.517 (2)	0.071 (8)*
H52	−0.065 (5)	0.1205 (9)	0.435 (2)	0.064 (7)*
H61	0.377 (5)	0.1892 (11)	0.660 (3)	0.084 (9)*
H62	0.332 (6)	0.1423 (12)	0.723 (3)	0.101 (11)*
H63	0.225 (5)	0.1914 (11)	0.753 (3)	0.088 (9)*
H64	−0.042 (6)	0.0988 (12)	0.662 (3)	0.095 (10)*
H65	−0.153 (6)	0.1435 (12)	0.718 (3)	0.106 (11)*
H66	−0.278 (6)	0.1247 (10)	0.581 (3)	0.085 (10)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0890 (13)	0.0762 (12)	0.0653 (11)	0.0142 (10)	0.0483 (10)	0.0033 (9)
N1	0.0548 (11)	0.0544 (11)	0.0450 (9)	0.0007 (9)	0.0245 (8)	−0.0019 (8)
N2	0.0610 (13)	0.0693 (13)	0.0575 (12)	−0.0088 (10)	0.0260 (10)	−0.0193 (10)
C2	0.0637 (14)	0.0500 (13)	0.0513 (12)	0.0010 (11)	0.0283 (11)	0.0037 (10)
C3	0.0586 (14)	0.0618 (15)	0.0447 (12)	−0.0036 (12)	0.0217 (11)	−0.0007 (11)
C4	0.0516 (14)	0.0589 (14)	0.0477 (12)	−0.0056 (11)	0.0199 (10)	−0.0142 (10)
C5	0.0649 (16)	0.0508 (14)	0.0585 (14)	−0.0013 (13)	0.0233 (13)	−0.0046 (12)
C6	0.0579 (14)	0.0545 (13)	0.0476 (12)	0.0025 (11)	0.0208 (11)	0.0045 (10)
C7	0.0524 (14)	0.0658 (15)	0.0538 (13)	−0.0028 (12)	0.0182 (11)	−0.0122 (12)
C11	0.0515 (13)	0.0572 (14)	0.0495 (12)	0.0005 (11)	0.0189 (10)	−0.0064 (10)
C12	0.096 (2)	0.121 (3)	0.088 (2)	−0.050 (2)	0.0635 (19)	−0.050 (2)
C13	0.102 (3)	0.126 (3)	0.097 (2)	−0.061 (2)	0.061 (2)	−0.060 (2)
C14	0.0609 (14)	0.0493 (13)	0.0487 (12)	0.0047 (11)	0.0217 (11)	−0.0012 (10)
C15	0.078 (2)	0.170 (4)	0.103 (2)	−0.049 (2)	0.059 (2)	−0.075 (3)
C16	0.076 (2)	0.183 (4)	0.107 (3)	−0.056 (3)	0.054 (2)	−0.089 (3)
C21	0.096 (2)	0.0610 (17)	0.0746 (19)	−0.0215 (16)	0.0427 (18)	−0.0146 (15)
C22	0.092 (2)	0.074 (2)	0.0728 (19)	0.0284 (18)	0.0391 (18)	0.0184 (17)
C41	0.0725 (16)	0.0516 (14)	0.0494 (13)	0.0076 (12)	0.0243 (12)	−0.0011 (10)
C42	0.118 (3)	0.109 (3)	0.106 (3)	−0.044 (2)	0.067 (2)	−0.057 (2)
C43	0.153 (4)	0.128 (3)	0.127 (3)	−0.057 (3)	0.079 (3)	−0.078 (3)
C44	0.143 (3)	0.093 (3)	0.0661 (19)	−0.003 (2)	0.049 (2)	−0.0252 (18)
C45	0.132 (3)	0.114 (3)	0.072 (2)	−0.013 (3)	0.061 (2)	−0.017 (2)
C46	0.098 (2)	0.098 (2)	0.0647 (18)	−0.017 (2)	0.0430 (17)	−0.0184 (16)
C61	0.0723 (19)	0.089 (2)	0.0514 (15)	0.0098 (17)	0.0124 (14)	0.0033 (15)
C62	0.089 (2)	0.069 (2)	0.081 (2)	0.0013 (17)	0.0435 (19)	0.0168 (16)

Geometric parameters (Å, º)

O1—N1	1.284 (2)	C14—C41	1.491 (3)
N1—C6	1.489 (3)	C15—C16	1.384 (4)
N1—C2	1.493 (3)	C15—H15	0.91 (4)
N2—C7	1.238 (3)	C16—H16	0.88 (4)
N2—C4	1.470 (3)	C21—H21	1.04 (3)
C2—C3	1.525 (3)	C21—H22	0.96 (3)
C2—C21	1.530 (4)	C21—H23	1.00 (3)
C2—C22	1.531 (4)	C22—H24	0.99 (3)
C3—C4	1.516 (3)	C22—H25	1.04 (4)
C3—H31	0.97 (3)	C22—H26	0.96 (3)
C3—H32	0.99 (3)	C41—C42	1.364 (4)
C4—C5	1.519 (3)	C41—C46	1.370 (4)
C4—H4	1.01 (2)	C42—C43	1.389 (5)
C5—C6	1.524 (3)	C42—H42	0.87 (4)
C5—H51	0.95 (3)	C43—C44	1.346 (5)
C5—H52	1.02 (3)	C43—H43	0.90 (5)
C6—C62	1.531 (4)	C44—C45	1.350 (5)
C6—C61	1.533 (4)	C44—H44	0.91 (4)
C7—C11	1.474 (3)	C45—C46	1.392 (4)
C7—H7	0.98 (3)	C45—H45	1.00 (4)
C11—C12	1.349 (4)	C46—H46	1.00 (4)
C11—C16	1.360 (4)	C61—H61	1.00 (3)
C12—C13	1.375 (4)	C61—H62	0.96 (3)
C12—H12	0.94 (4)	C61—H63	1.00 (3)
C13—C14	1.360 (4)	C62—H64	1.00 (3)
C13—H13	0.87 (4)	C62—H65	1.03 (3)
C14—C15	1.355 (4)	C62—H66	1.01 (3)
O1···O1^i	5.955 (1)	O1···H61^i	2.85 (3)
O1···O1^ii	6.0910 (13)	O1···H21^i	2.81 (3)
O1···C22^ii	3.516 (4)	O1···H26^ii	2.70 (3)
O1···C3^ii	3.445 (3)	O1···H31^ii	2.83 (3)
O1—N1—C6	116.39 (17)	C14—C15—C16	122.2 (3)
O1—N1—C2	116.32 (18)	C14—C15—H15	118 (3)
C6—N1—C2	123.52 (17)	C16—C15—H15	120 (3)
C7—N2—C4	120.7 (2)	C11—C16—C15	121.5 (3)
N1—C2—C3	108.95 (18)	C11—C16—H16	118 (3)
N1—C2—C21	109.8 (2)	C15—C16—H16	120 (3)
C3—C2—C21	111.9 (2)	C2—C21—H21	111.2 (17)
N1—C2—C22	107.2 (2)	C2—C21—H22	110.2 (19)
C3—C2—C22	108.8 (2)	H21—C21—H22	107 (3)
C21—C2—C22	110.0 (3)	C2—C21—H23	107.2 (18)
C4—C3—C2	115.67 (19)	H21—C21—H23	110 (2)
C4—C3—H31	108.6 (15)	H22—C21—H23	111 (2)
C2—C3—H31	109.2 (15)	C2—C22—H24	108.6 (18)
C4—C3—H32	107.5 (15)	C2—C22—H25	112.6 (19)
C2—C3—H32	109.9 (15)	H24—C22—H25	109 (3)
H31—C3—H32	105 (2)	C2—C22—H26	110.0 (19)
N2—C4—C3	107.59 (19)	H24—C22—H26	109 (3)
N2—C4—C5	107.72 (19)	H25—C22—H26	107 (3)
C3—C4—C5	108.8 (2)	C42—C41—C46	116.7 (3)
N2—C4—H4	110.9 (12)	C42—C41—C14	121.1 (2)
C3—C4—H4	110.5 (12)	C46—C41—C14	122.2 (2)
C5—C4—H4	111.2 (12)	C41—C42—C43	122.2 (3)
C4—C5—C6	115.3 (2)	C41—C42—H42	119 (3)
C4—C5—H51	110.6 (16)	C43—C42—H42	119 (3)
C6—C5—H51	107.9 (16)	C44—C43—C42	120.1 (4)
C4—C5—H52	106.9 (14)	C44—C43—H43	122 (3)
C6—C5—H52	110.8 (14)	C42—C43—H43	118 (3)
H51—C5—H52	105 (2)	C43—C44—C45	118.9 (3)
N1—C6—C5	109.08 (18)	C43—C44—H44	118 (3)
N1—C6—C62	107.6 (2)	C45—C44—H44	122 (3)
C5—C6—C62	109.3 (2)	C44—C45—C46	121.2 (3)
N1—C6—C61	109.6 (2)	C44—C45—H45	122 (2)
C5—C6—C61	111.9 (2)	C46—C45—H45	117 (2)
C62—C6—C61	109.3 (2)	C41—C46—C45	120.8 (3)
N2—C7—C11	122.1 (2)	C41—C46—H46	120 (2)
N2—C7—H7	119.7 (17)	C45—C46—H46	119 (2)
C11—C7—H7	118.1 (17)	C6—C61—H61	112.8 (17)
C12—C11—C16	116.5 (2)	C6—C61—H62	109 (2)
C12—C11—C7	120.6 (2)	H61—C61—H62	108 (3)
C16—C11—C7	122.9 (2)	C6—C61—H63	109.8 (17)
C11—C12—C13	121.6 (3)	H61—C61—H63	106 (2)
C11—C12—H12	117 (2)	H62—C61—H63	111 (2)
C13—C12—H12	122 (2)	C6—C62—H64	106.4 (18)
C14—C13—C12	122.8 (3)	C6—C62—H65	112.8 (19)
C14—C13—H13	123 (3)	H64—C62—H65	109 (2)
C12—C13—H13	114 (3)	C6—C62—H66	109.5 (17)
C15—C14—C13	115.3 (2)	H64—C62—H66	109 (3)
C15—C14—C41	123.3 (2)	H65—C62—H66	109 (2)
C13—C14—C41	121.4 (2)
O1—N1—C2—C3	−162.3 (2)	N2—C7—C11—C12	−6.2 (4)
C6—N1—C2—C3	40.4 (3)	N2—C7—C11—C16	171.1 (3)
O1—N1—C2—C21	74.9 (3)	C16—C11—C12—C13	1.3 (6)
C6—N1—C2—C21	−82.4 (3)	C7—C11—C12—C13	178.7 (4)
O1—N1—C2—C22	−44.7 (3)	C11—C12—C13—C14	0.2 (7)
C6—N1—C2—C22	158.1 (2)	C12—C13—C14—C15	−2.0 (6)
N1—C2—C3—C4	−46.4 (3)	C12—C13—C14—C41	179.2 (3)
C21—C2—C3—C4	75.2 (3)	C13—C14—C15—C16	2.3 (6)
C22—C2—C3—C4	−163.0 (2)	C41—C14—C15—C16	−179.0 (4)
C7—N2—C4—C3	106.8 (3)	C12—C11—C16—C15	−1.0 (6)
C7—N2—C4—C5	−136.1 (3)	C7—C11—C16—C15	−178.4 (4)
C2—C3—C4—N2	171.8 (2)	C14—C15—C16—C11	−0.8 (8)
C2—C3—C4—C5	55.4 (3)	C15—C14—C41—C42	176.0 (4)
N2—C4—C5—C6	−172.0 (2)	C13—C14—C41—C42	−5.3 (5)
C3—C4—C5—C6	−55.7 (3)	C15—C14—C41—C46	−4.9 (5)
O1—N1—C6—C5	161.9 (2)	C13—C14—C41—C46	173.8 (3)
C2—N1—C6—C5	−40.9 (3)	C46—C41—C42—C43	0.7 (6)
O1—N1—C6—C62	43.4 (3)	C14—C41—C42—C43	179.9 (4)
C2—N1—C6—C62	−159.4 (2)	C41—C42—C43—C44	1.0 (8)
O1—N1—C6—C61	−75.3 (3)	C42—C43—C44—C45	−1.9 (8)
C2—N1—C6—C61	82.0 (3)	C43—C44—C45—C46	1.3 (7)
C4—C5—C6—N1	47.1 (3)	C42—C41—C46—C45	−1.4 (5)
C4—C5—C6—C62	164.4 (2)	C14—C41—C46—C45	179.5 (3)
C4—C5—C6—C61	−74.4 (3)	C44—C45—C46—C41	0.4 (6)
C4—N2—C7—C11	−176.9 (2)

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

(6) 4-(4-pyridyl)methyleneamino-2,2,6,6-tetramethylpiperidin-1-oxyl

Crystal data

C15H22N3O	F(000) = 564.00
Mr = 260.36	Dx = 1.167 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 7.977 (6) Å	Cell parameters from 25 reflections
b = 20.158 (7) Å	θ = 14.3–17.3°
c = 11.383 (9) Å	µ = 0.08 mm^−1
β = 125.95 (6)°	T = 295 K
V = 1481 (1) Å^3	Prism, orange
Z = 4	0.30 × 0.30 × 0.30 mm

Data collection

Rigaku AFC7R diffractometer	Rint = 0.019
Radiation source: Rigaku rotating anode	θmax = 27.5°, θmin = 2.0°
Graphite monochromator	h = −10→0
ω–2θ scans	k = −26→0
3631 measured reflections	l = −11→14
3400 independent reflections	3 standard reflections every 150 reflections
2464 reflections with I > 2σ(I)	intensity decay: −0.1%

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.041	Hydrogen site location: difference Fourier map
wR(F^2) = 0.120	All H-atom parameters refined
S = 1.00	Calculated w = 1/[σ^2(Fo^2) + (0.0537P)^2 + 0.2298P] where P = (Fo^2 + 2Fc^2)/3
3400 reflections	(Δ/σ)max = 0.001
260 parameters	Δρmax = 0.15 e Å^−3
0 restraints	Δρmin = −0.19 e Å^−3

Special details

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

Refinement. Refinement 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 (Ų)

	x	y	z	Uiso*/Ueq
O1	0.66692 (17)	0.20588 (5)	0.68638 (10)	0.0614 (3)
N1	0.57579 (17)	0.18079 (5)	0.55966 (10)	0.0426 (2)
N2	0.32248 (19)	0.08646 (6)	0.15827 (12)	0.0556 (3)
N14	0.1225 (2)	−0.02359 (7)	−0.30557 (13)	0.0618 (3)
C2	0.5925 (2)	0.21876 (6)	0.45395 (13)	0.0449 (3)
C3	0.5402 (2)	0.17283 (7)	0.32952 (14)	0.0486 (3)
C4	0.3435 (2)	0.13250 (7)	0.26638 (14)	0.0494 (3)
C5	0.3671 (3)	0.09152 (7)	0.38637 (17)	0.0533 (3)
C6	0.4072 (2)	0.13205 (6)	0.51462 (14)	0.0476 (3)
C7	0.1824 (2)	0.09644 (8)	0.02753 (16)	0.0546 (3)
C11	0.1579 (2)	0.05324 (7)	−0.08720 (14)	0.0500 (3)
C12	0.0459 (2)	0.07502 (8)	−0.22893 (16)	0.0596 (4)
C13	0.0340 (3)	0.03546 (9)	−0.33276 (16)	0.0623 (4)
C15	0.2279 (3)	−0.04471 (9)	−0.16901 (17)	0.0645 (4)
C16	0.2495 (2)	−0.00854 (8)	−0.05737 (16)	0.0594 (4)
C21	0.8150 (3)	0.24249 (10)	0.5323 (2)	0.0655 (4)
C22	0.4489 (3)	0.27924 (8)	0.40051 (19)	0.0627 (4)
C61	0.2127 (3)	0.16838 (9)	0.4769 (2)	0.0613 (4)
C62	0.4821 (4)	0.08522 (8)	0.6422 (2)	0.0661 (4)
H4	0.220 (2)	0.1627 (7)	0.2193 (15)	0.051 (4)*
H7	0.082 (3)	0.1336 (9)	−0.0051 (18)	0.076 (5)*
H12	−0.022 (3)	0.1174 (9)	−0.2521 (19)	0.078 (5)*
H13	−0.049 (3)	0.0500 (8)	−0.436 (2)	0.077 (5)*
H15	0.294 (3)	−0.0890 (10)	−0.1486 (19)	0.084 (6)*
H16	0.330 (3)	−0.0255 (8)	0.036 (2)	0.073 (5)*
H21	0.907 (3)	0.2050 (10)	0.574 (2)	0.082 (6)*
H22	0.831 (3)	0.2648 (10)	0.463 (2)	0.094 (6)*
H23	0.846 (3)	0.2743 (9)	0.608 (2)	0.078 (5)*
H24	0.297 (3)	0.2678 (10)	0.335 (2)	0.085 (6)*
H25	0.475 (3)	0.3036 (9)	0.482 (2)	0.082 (5)*
H26	0.478 (3)	0.3088 (10)	0.348 (2)	0.099 (7)*
H31	0.660 (2)	0.1408 (8)	0.3669 (16)	0.059 (4)*
H32	0.530 (2)	0.2005 (8)	0.2524 (17)	0.063 (4)*
H51	0.244 (3)	0.0638 (8)	0.3487 (17)	0.066 (5)*
H52	0.490 (2)	0.0604 (7)	0.4235 (16)	0.055 (4)*
H61	0.112 (3)	0.1383 (10)	0.4606 (19)	0.082 (6)*
H62	0.248 (3)	0.1981 (9)	0.5561 (19)	0.075 (5)*
H63	0.145 (3)	0.1973 (9)	0.386 (2)	0.076 (5)*
H64	0.615 (3)	0.0634 (10)	0.675 (2)	0.089 (6)*
H65	0.375 (3)	0.0500 (10)	0.611 (2)	0.090 (6)*
H66	0.511 (3)	0.1101 (10)	0.726 (2)	0.085 (6)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0810 (7)	0.0637 (6)	0.0419 (5)	−0.0090 (5)	0.0375 (5)	−0.0116 (4)
N1	0.0540 (6)	0.0399 (5)	0.0381 (5)	0.0006 (4)	0.0294 (5)	−0.0023 (4)
N2	0.0587 (7)	0.0626 (7)	0.0485 (6)	−0.0005 (6)	0.0332 (6)	−0.0140 (5)
N14	0.0656 (8)	0.0754 (9)	0.0488 (7)	−0.0134 (7)	0.0361 (6)	−0.0173 (6)
C2	0.0550 (7)	0.0429 (6)	0.0400 (6)	−0.0044 (5)	0.0297 (6)	−0.0001 (5)
C3	0.0601 (8)	0.0519 (7)	0.0423 (7)	−0.0035 (6)	0.0348 (6)	−0.0024 (6)
C4	0.0516 (7)	0.0529 (7)	0.0450 (7)	0.0010 (6)	0.0290 (6)	−0.0111 (6)
C5	0.0662 (9)	0.0463 (7)	0.0653 (9)	−0.0117 (7)	0.0486 (8)	−0.0157 (6)
C6	0.0621 (8)	0.0416 (6)	0.0556 (7)	−0.0041 (6)	0.0438 (7)	−0.0066 (5)
C7	0.0555 (8)	0.0576 (8)	0.0510 (8)	0.0013 (7)	0.0314 (7)	−0.0074 (6)
C11	0.0479 (7)	0.0574 (8)	0.0447 (7)	−0.0061 (6)	0.0272 (6)	−0.0097 (6)
C12	0.0639 (9)	0.0591 (9)	0.0498 (8)	−0.0024 (7)	0.0301 (7)	−0.0019 (7)
C13	0.0665 (9)	0.0752 (11)	0.0428 (7)	−0.0142 (8)	0.0308 (7)	−0.0050 (7)
C15	0.0693 (10)	0.0658 (10)	0.0545 (8)	0.0035 (8)	0.0342 (8)	−0.0109 (7)
C16	0.0629 (9)	0.0661 (9)	0.0417 (7)	0.0036 (7)	0.0266 (7)	−0.0041 (6)
C21	0.0656 (10)	0.0730 (11)	0.0593 (9)	−0.0208 (9)	0.0374 (8)	−0.0073 (8)
C22	0.0844 (12)	0.0420 (7)	0.0576 (9)	0.0055 (7)	0.0395 (9)	0.0052 (7)
C61	0.0641 (9)	0.0651 (9)	0.0730 (10)	−0.0033 (8)	0.0505 (9)	−0.0136 (8)
C62	0.1050 (14)	0.0474 (8)	0.0774 (11)	0.0006 (9)	0.0711 (11)	0.0036 (8)

Geometric parameters (Å, º)

O1—N1	1.2782 (17)	C7—H7	0.996 (18)
N1—C6	1.4926 (19)	C11—C12	1.379 (2)
N1—C2	1.4963 (17)	C11—C16	1.381 (2)
N2—C7	1.246 (2)	C12—C13	1.382 (2)
N2—C4	1.4701 (17)	C12—H12	0.961 (18)
N14—C13	1.325 (2)	C13—H13	0.992 (18)
N14—C15	1.330 (2)	C15—C16	1.385 (2)
C2—C21	1.522 (3)	C15—H15	0.993 (19)
C2—C3	1.5308 (19)	C16—H16	0.930 (18)
C2—C22	1.533 (2)	C21—H21	0.96 (2)
C3—C4	1.521 (2)	C21—H22	0.98 (2)
C3—H31	1.014 (16)	C21—H23	0.980 (19)
C3—H32	1.003 (15)	C22—H24	1.01 (2)
C4—C5	1.510 (2)	C22—H25	0.961 (19)
C4—H4	1.003 (15)	C22—H26	0.96 (2)
C5—C6	1.534 (2)	C61—H61	0.94 (2)
C5—H51	0.981 (17)	C61—H62	0.977 (18)
C5—H52	1.026 (16)	C61—H63	1.024 (18)
C6—C62	1.529 (2)	C62—H64	1.00 (2)
C6—C61	1.531 (2)	C62—H65	1.00 (2)
C7—C11	1.484 (2)	C62—H66	0.98 (2)
O1···O1^i	7.977 (6)	O1···C3^ii	3.404 (2)
O1···O1^ii	5.963 (4)	O1···C21^ii	3.539 (4)
O1···O1^iii	6.774 (7)	O1···H22^ii	2.67 (2)
O1···C22^ii	3.746 (3)	O1···H32^ii	2.51 (2)
O1—N1—C6	116.67 (11)	C12—C11—C7	120.20 (14)
O1—N1—C2	116.42 (11)	C16—C11—C7	122.36 (14)
C6—N1—C2	123.23 (11)	C11—C12—C13	119.28 (16)
C7—N2—C4	118.66 (13)	C11—C12—H12	118.6 (11)
C13—N14—C15	116.42 (13)	C13—C12—H12	122.2 (11)
N1—C2—C21	108.24 (13)	N14—C13—C12	123.99 (15)
N1—C2—C3	109.28 (11)	N14—C13—H13	115.8 (10)
C21—C2—C3	108.84 (13)	C12—C13—H13	120.2 (10)
N1—C2—C22	109.12 (12)	N14—C15—C16	123.81 (17)
C21—C2—C22	108.97 (14)	N14—C15—H15	116.4 (11)
C3—C2—C22	112.30 (13)	C16—C15—H15	119.7 (11)
C4—C3—C2	113.93 (12)	C11—C16—C15	119.07 (15)
C4—C3—H31	108.1 (9)	C11—C16—H16	121.6 (11)
C2—C3—H31	108.5 (9)	C15—C16—H16	119.2 (11)
C4—C3—H32	110.7 (9)	C2—C21—H21	109.3 (11)
C2—C3—H32	108.2 (9)	C2—C21—H22	109.2 (12)
H31—C3—H32	107.2 (12)	H21—C21—H22	110.0 (17)
N2—C4—C5	107.70 (12)	C2—C21—H23	109.1 (11)
N2—C4—C3	108.19 (12)	H21—C21—H23	110.5 (15)
C5—C4—C3	108.57 (13)	H22—C21—H23	108.8 (16)
N2—C4—H4	110.0 (8)	C2—C22—H24	113.9 (11)
C5—C4—H4	112.2 (8)	C2—C22—H25	109.5 (11)
C3—C4—H4	110.1 (8)	H24—C22—H25	108.2 (16)
C4—C5—C6	114.53 (12)	C2—C22—H26	110.1 (13)
C4—C5—H51	110.7 (9)	H24—C22—H26	108.1 (16)
C6—C5—H51	108.5 (9)	H25—C22—H26	106.7 (16)
C4—C5—H52	106.7 (8)	C6—C61—H61	110.9 (12)
C6—C5—H52	108.7 (8)	C6—C61—H62	110.0 (10)
H51—C5—H52	107.4 (13)	H61—C61—H62	109.0 (16)
N1—C6—C62	108.00 (14)	C6—C61—H63	113.7 (10)
N1—C6—C61	109.98 (12)	H61—C61—H63	106.7 (15)
C62—C6—C61	109.19 (14)	H62—C61—H63	106.4 (14)
N1—C6—C5	108.64 (11)	C6—C62—H64	111.3 (12)
C62—C6—C5	108.78 (13)	C6—C62—H65	108.7 (12)
C61—C6—C5	112.15 (14)	H64—C62—H65	108.4 (16)
N2—C7—C11	121.26 (15)	C6—C62—H66	110.4 (11)
N2—C7—H7	121.9 (10)	H64—C62—H66	106.0 (16)
C11—C7—H7	116.8 (10)	H65—C62—H66	112.1 (16)
C12—C11—C16	117.42 (13)
O1—N1—C2—C21	43.19 (16)	C2—N1—C6—C61	−82.40 (15)
C6—N1—C2—C21	−159.17 (13)	O1—N1—C6—C5	−161.72 (11)
O1—N1—C2—C3	161.59 (11)	C2—N1—C6—C5	40.69 (16)
C6—N1—C2—C3	−40.77 (16)	C4—C5—C6—N1	−48.31 (17)
O1—N1—C2—C22	−75.26 (16)	C4—C5—C6—C62	−165.65 (14)
C6—N1—C2—C22	82.38 (15)	C4—C5—C6—C61	73.46 (16)
N1—C2—C3—C4	47.67 (16)	C4—N2—C7—C11	177.72 (12)
C21—C2—C3—C4	165.68 (13)	N2—C7—C11—C12	−161.08 (15)
C22—C2—C3—C4	−73.57 (17)	N2—C7—C11—C16	16.8 (2)
C7—N2—C4—C5	133.09 (15)	C16—C11—C12—C13	−1.4 (2)
C7—N2—C4—C3	−109.73 (17)	C7—C11—C12—C13	176.66 (14)
C2—C3—C4—N2	−174.81 (11)	C15—N14—C13—C12	0.1 (2)
C2—C3—C4—C5	−58.19 (16)	C11—C12—C13—N14	0.8 (2)
N2—C4—C5—C6	175.69 (12)	C13—N14—C15—C16	−0.5 (2)
C3—C4—C5—C6	58.76 (16)	C12—C11—C16—C15	1.1 (2)
O1—N1—C6—C62	−43.88 (15)	C7—C11—C16—C15	−176.92 (14)
C2—N1—C6—C62	158.53 (12)	N14—C15—C16—C11	−0.1 (3)
O1—N1—C6—C61	75.19 (15)

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

(7) 4-(3,5-dichlorophenyl)methyleneamino-2,2,6,6-tetramethylpiperidin-1-oxyl

Crystal data

C16H21Cl2N2O	F(000) = 1384.00
Mr = 328.26	Dx = 1.263 Mg m^−3
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 25 reflections
a = 14.035 (3) Å	θ = 14.1–17.8°
b = 22.964 (3) Å	µ = 0.38 mm^−1
c = 10.710 (2) Å	T = 295 K
V = 3451.9 (9) Å^3	Prism, orange
Z = 8	0.40 × 0.20 × 0.20 mm

Data collection

Rigaku AFC5R diffractometer	2128 reflections with I > 2σ(I)
Radiation source: Rigaku rotating anode	Rint = 0.028
Graphite monochromator	θmax = 27.5°, θmin = 2.9°
ω–2θ scans	h = −1→18
Absorption correction: integration ?	k = −1→29
Tmin = 0.927, Tmax = 0.934	l = −1→13
4927 measured reflections	3 standard reflections every 100 reflections
3959 independent reflections	intensity decay: −0.4%

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.049	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.123	All H-atom parameters refined
S = 1.00	Calculated w = 1/[σ^2(Fo^2) + (0.0369P)^2 + 2.060P] where P = (Fo^2 + 2Fc^2)/3
3959 reflections	(Δ/σ)max = 0.001
274 parameters	Δρmax = 0.37 e Å^−3
0 restraints	Δρmin = −0.28 e Å^−3

Special details

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

Refinement. Refinement 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 (Ų)

	x	y	z	Uiso*/Ueq
Cl1	0.12604 (6)	−0.04521 (4)	−0.28124 (8)	0.0682 (3)
Cl2	0.43007 (6)	0.08783 (4)	−0.37751 (9)	0.0791 (3)
O1	−0.03302 (16)	0.19379 (9)	0.49966 (17)	0.0579 (6)
N1	0.01245 (16)	0.17800 (10)	0.40146 (19)	0.0418 (6)
N2	0.14398 (17)	0.11600 (11)	0.0744 (2)	0.0487 (6)
C2	0.09738 (19)	0.14025 (13)	0.4217 (2)	0.0463 (7)
C3	0.1249 (3)	0.11150 (15)	0.2979 (3)	0.0499 (8)
C4	0.1265 (2)	0.15156 (13)	0.1858 (3)	0.0454 (7)
C5	0.0294 (2)	0.17977 (14)	0.1728 (3)	0.0428 (7)
C6	−0.00257 (19)	0.21422 (12)	0.2875 (2)	0.0416 (7)
C7	0.2145 (2)	0.12751 (13)	0.0064 (3)	0.0435 (7)
C11	0.23550 (18)	0.09205 (12)	−0.1052 (2)	0.0386 (6)
C12	0.1775 (2)	0.04533 (12)	−0.1372 (3)	0.0402 (6)
C13	0.19897 (19)	0.01287 (12)	−0.2410 (2)	0.0417 (6)
C14	0.2769 (2)	0.02516 (13)	−0.3152 (3)	0.0446 (7)
C15	0.3332 (2)	0.07152 (13)	−0.2828 (3)	0.0457 (7)
C16	0.3141 (2)	0.10468 (14)	−0.1787 (3)	0.0454 (7)
C21	0.0687 (3)	0.09282 (18)	0.5143 (3)	0.0652 (10)
C22	0.1794 (3)	0.1764 (2)	0.4747 (4)	0.0669 (11)
C61	−0.1084 (2)	0.22702 (19)	0.2764 (4)	0.0610 (9)
C62	0.0523 (3)	0.27139 (15)	0.2998 (3)	0.0580 (9)
H4	0.1743 (18)	0.1801 (11)	0.195 (2)	0.036 (7)*
H7	0.2581 (19)	0.1604 (12)	0.025 (2)	0.047 (8)*
H12	0.1245 (17)	0.0365 (10)	−0.091 (2)	0.032 (7)*
H14	0.2890 (18)	0.0029 (12)	−0.385 (3)	0.052 (8)*
H16	0.3517 (16)	0.1326 (10)	−0.155 (2)	0.025 (7)*
H21	0.120 (3)	0.0632 (16)	0.516 (3)	0.093 (13)*
H22	0.008 (3)	0.0688 (18)	0.484 (4)	0.118 (16)*
H23	0.062 (2)	0.1064 (14)	0.592 (3)	0.068 (11)*
H24	0.209 (2)	0.2080 (14)	0.414 (3)	0.075 (11)*
H25	0.228 (3)	0.1512 (16)	0.498 (3)	0.093 (14)*
H26	0.160 (3)	0.1998 (16)	0.546 (3)	0.093 (13)*
H31	0.083 (2)	0.0818 (12)	0.282 (3)	0.050 (9)*
H32	0.185 (2)	0.0932 (12)	0.309 (3)	0.051 (8)*
H51	−0.0175 (18)	0.1498 (11)	0.155 (2)	0.041 (7)*
H52	0.0280 (18)	0.2053 (12)	0.103 (3)	0.045 (8)*
H61	−0.146 (2)	0.1907 (14)	0.281 (3)	0.059 (9)*
H62	−0.119 (2)	0.2485 (14)	0.199 (3)	0.062 (9)*
H63	−0.132 (2)	0.2504 (16)	0.344 (3)	0.085 (12)*
H64	0.125 (2)	0.2689 (14)	0.297 (3)	0.076 (11)*
H65	0.036 (2)	0.2972 (13)	0.236 (3)	0.062 (10)*
H66	0.034 (2)	0.2916 (14)	0.376 (3)	0.069 (10)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cl1	0.0633 (5)	0.0636 (5)	0.0778 (6)	−0.0187 (4)	0.0007 (5)	−0.0197 (4)
Cl2	0.0710 (6)	0.0875 (7)	0.0786 (6)	−0.0172 (5)	0.0406 (5)	−0.0182 (5)
O1	0.0683 (14)	0.0695 (14)	0.0361 (10)	0.0107 (12)	0.0172 (10)	0.0025 (11)
N1	0.0454 (13)	0.0500 (14)	0.0301 (12)	0.0030 (11)	0.0071 (10)	0.0029 (10)
N2	0.0529 (15)	0.0549 (15)	0.0382 (13)	−0.0006 (12)	0.0070 (12)	−0.0105 (12)
C2	0.0466 (16)	0.0575 (18)	0.0346 (14)	0.0077 (14)	−0.0014 (13)	−0.0007 (14)
C3	0.0510 (18)	0.055 (2)	0.0433 (17)	0.0117 (18)	−0.0012 (15)	−0.0015 (15)
C4	0.0446 (16)	0.0531 (18)	0.0385 (15)	−0.0040 (15)	0.0074 (13)	−0.0129 (14)
C5	0.0499 (17)	0.0504 (18)	0.0279 (14)	−0.0007 (16)	0.0022 (13)	0.0000 (14)
C6	0.0458 (15)	0.0468 (16)	0.0321 (14)	0.0038 (13)	0.0038 (13)	0.0049 (13)
C7	0.0460 (16)	0.0477 (18)	0.0367 (15)	0.0003 (15)	0.0000 (13)	−0.0056 (14)
C11	0.0394 (14)	0.0424 (15)	0.0341 (14)	0.0043 (13)	0.0010 (12)	−0.0002 (12)
C12	0.0366 (15)	0.0463 (17)	0.0377 (15)	0.0019 (13)	0.0005 (13)	0.0035 (13)
C13	0.0405 (14)	0.0445 (16)	0.0400 (15)	−0.0002 (13)	−0.0042 (13)	−0.0036 (13)
C14	0.0492 (17)	0.0497 (18)	0.0348 (15)	0.0034 (15)	0.0033 (13)	−0.0081 (14)
C15	0.0428 (15)	0.0513 (17)	0.0429 (16)	−0.0012 (14)	0.0093 (13)	−0.0017 (14)
C16	0.0429 (16)	0.0492 (19)	0.0442 (16)	−0.0044 (15)	0.0005 (14)	−0.0063 (14)
C21	0.087 (3)	0.067 (2)	0.0413 (19)	0.018 (2)	0.001 (2)	0.0121 (18)
C22	0.056 (2)	0.094 (3)	0.050 (2)	0.001 (2)	−0.0081 (18)	−0.010 (2)
C61	0.055 (2)	0.073 (3)	0.055 (2)	0.0192 (19)	0.0059 (18)	0.014 (2)
C62	0.081 (3)	0.049 (2)	0.0446 (19)	−0.0023 (18)	0.0118 (19)	0.0000 (17)

Geometric parameters (Å, º)

Cl1—C13	1.736 (3)	C11—C16	1.386 (4)
Cl2—C15	1.736 (3)	C11—C12	1.389 (4)
O1—N1	1.283 (3)	C12—C13	1.372 (4)
N1—C2	1.490 (3)	C12—H12	0.92 (2)
N1—C6	1.492 (3)	C13—C14	1.381 (4)
N2—C7	1.257 (3)	C14—C15	1.371 (4)
N2—C4	1.467 (3)	C14—H14	0.92 (3)
C2—C21	1.527 (5)	C15—C16	1.377 (4)
C2—C22	1.528 (5)	C16—H16	0.87 (2)
C2—C3	1.531 (4)	C21—H21	0.99 (4)
C3—C4	1.513 (4)	C21—H22	1.06 (4)
C3—H31	0.92 (3)	C21—H23	0.89 (3)
C3—H32	0.95 (3)	C22—H24	1.06 (3)
C4—C5	1.515 (4)	C22—H25	0.93 (4)
C4—H4	0.94 (2)	C22—H26	0.97 (4)
C5—C6	1.528 (4)	C61—H61	0.99 (3)
C5—H51	0.97 (3)	C61—H62	0.98 (3)
C5—H52	0.95 (3)	C61—H63	0.96 (4)
C6—C61	1.519 (4)	C62—H64	1.03 (3)
C6—C62	1.528 (4)	C62—H65	0.93 (3)
C7—C11	1.476 (4)	C62—H66	0.97 (3)
C7—H7	0.99 (3)
O1···O1^i	5.945 (2)	O1···C62^i	3.522 (5)
O1···O1^ii	7.477 (2)	O1···H65^i	2.72 (3)
O1···C5^i	3.554 (4)	O1···H52^i	2.71 (3)
O1—N1—C2	116.3 (2)	C13—C12—C11	119.4 (3)
O1—N1—C6	116.3 (2)	C13—C12—H12	119.9 (15)
C2—N1—C6	123.8 (2)	C11—C12—H12	120.7 (15)
C7—N2—C4	119.1 (3)	C12—C13—C14	121.9 (3)
N1—C2—C21	107.4 (3)	C12—C13—Cl1	119.3 (2)
N1—C2—C22	109.9 (3)	C14—C13—Cl1	118.8 (2)
C21—C2—C22	110.2 (3)	C15—C14—C13	118.1 (3)
N1—C2—C3	109.1 (2)	C15—C14—H14	121.9 (17)
C21—C2—C3	108.7 (3)	C13—C14—H14	120.0 (17)
C22—C2—C3	111.5 (3)	C14—C15—C16	121.4 (3)
C4—C3—C2	115.4 (2)	C14—C15—Cl2	118.1 (2)
C4—C3—H31	108.5 (18)	C16—C15—Cl2	120.4 (2)
C2—C3—H31	108.4 (18)	C15—C16—C11	120.0 (3)
C4—C3—H32	110.9 (17)	C15—C16—H16	121.5 (15)
C2—C3—H32	107.6 (17)	C11—C16—H16	118.4 (15)
H31—C3—H32	106 (2)	C2—C21—H21	108 (2)
N2—C4—C3	108.0 (2)	C2—C21—H22	113 (2)
N2—C4—C5	108.3 (2)	H21—C21—H22	103 (3)
C3—C4—C5	108.7 (2)	C2—C21—H23	113 (2)
N2—C4—H4	110.5 (15)	H21—C21—H23	108 (3)
C3—C4—H4	110.6 (15)	H22—C21—H23	112 (3)
C5—C4—H4	110.7 (15)	C2—C22—H24	116.3 (17)
C4—C5—C6	114.3 (2)	C2—C22—H25	108 (2)
C4—C5—H51	108.9 (15)	H24—C22—H25	108 (3)
C6—C5—H51	109.1 (15)	C2—C22—H26	112 (2)
C4—C5—H52	110.7 (16)	H24—C22—H26	102 (3)
C6—C5—H52	108.1 (16)	H25—C22—H26	110 (3)
H51—C5—H52	105 (2)	C6—C61—H61	110.6 (17)
N1—C6—C61	108.0 (2)	C6—C61—H62	108.4 (17)
N1—C6—C62	109.7 (2)	H61—C61—H62	113 (3)
C61—C6—C62	109.5 (3)	C6—C61—H63	113 (2)
N1—C6—C5	109.1 (2)	H61—C61—H63	105 (3)
C61—C6—C5	108.9 (3)	H62—C61—H63	108 (3)
C62—C6—C5	111.5 (2)	C6—C62—H64	116.9 (18)
N2—C7—C11	120.7 (3)	C6—C62—H65	111.2 (19)
N2—C7—H7	122.0 (15)	H64—C62—H65	105 (3)
C11—C7—H7	117.4 (15)	C6—C62—H66	110.6 (18)
C16—C11—C12	119.2 (3)	H64—C62—H66	108 (3)
C16—C11—C7	120.2 (3)	H65—C62—H66	104 (2)
C12—C11—C7	120.6 (2)
O1—N1—C2—C21	46.0 (3)	C2—N1—C6—C5	40.0 (3)
C6—N1—C2—C21	−156.2 (3)	C4—C5—C6—N1	−48.1 (3)
O1—N1—C2—C22	−73.8 (3)	C4—C5—C6—C61	−165.8 (3)
C6—N1—C2—C22	84.0 (3)	C4—C5—C6—C62	73.3 (3)
O1—N1—C2—C3	163.7 (2)	C4—N2—C7—C11	178.9 (2)
C6—N1—C2—C3	−38.5 (4)	N2—C7—C11—C16	−179.2 (3)
N1—C2—C3—C4	45.5 (4)	N2—C7—C11—C12	0.0 (4)
C21—C2—C3—C4	162.3 (3)	C16—C11—C12—C13	−0.3 (4)
C22—C2—C3—C4	−76.0 (4)	C7—C11—C12—C13	−179.6 (2)
C7—N2—C4—C3	−122.6 (3)	C11—C12—C13—C14	0.1 (4)
C7—N2—C4—C5	119.8 (3)	C11—C12—C13—Cl1	−179.6 (2)
C2—C3—C4—N2	−174.1 (3)	C12—C13—C14—C15	−0.3 (4)
C2—C3—C4—C5	−56.8 (4)	Cl1—C13—C14—C15	179.4 (2)
N2—C4—C5—C6	175.0 (2)	C13—C14—C15—C16	0.8 (4)
C3—C4—C5—C6	57.9 (3)	C13—C14—C15—Cl2	−178.9 (2)
O1—N1—C6—C61	−43.9 (3)	C14—C15—C16—C11	−1.1 (4)
C2—N1—C6—C61	158.3 (3)	Cl2—C15—C16—C11	178.6 (2)
O1—N1—C6—C62	75.4 (3)	C12—C11—C16—C15	0.8 (4)
C2—N1—C6—C62	−82.4 (3)	C7—C11—C16—C15	−179.9 (3)
O1—N1—C6—C5	−162.2 (2)

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