(R)-2-[1-(2,6-Dichloro-3,4,5-trimeth-oxy-benzo-yl)pyrrolidin-2-yl]-4,4,5,5-tetra-methyl-4,5-dihydro-1H-imidazole-1-oxyl 3-oxide.

In the title compound, C(21)H(28)Cl(2)N(3)O(6), the nitronyl nitroxide ring displays a half-chair conformation, whereas the pyrrolidine ring has an envelope conformation. These two rings are twisted to each other with N-C-C-N torsion angles around the connecting C-C bond of 48.9 (6) and -127.0 (5)°. The benzene ring is nearly perpendicular to the pyrrolidine ring, with torsion angles around the connecting C-C bond of 86.3 (6) and -97.7 (6)°. The crystal structure is stabilized by C-H⋯O and C-H⋯π hydrogen bonds, which build up a three-dimensional network.

Related literature

For the chemical and physical properties of nitronyl nitroxides, see: Minguet et al. (2001 ▶); Osiecki & Ullman (1968 ▶); Shemsi et al. (2007 ▶); Wu et al. (2006 ▶). For related structures, see: Shimono et al. (2004 ▶); Minguet et al. (2001 ▶); Tian et al. (2011 ▶). For puckering parameters, see Cremer & Pople (1975 ▶). For a description of the Cambridge Structural Database, see: Allen (2002 ▶).

Experimental

Crystal data

C21H28Cl2N3O6

M = 489.36

Orthorhombic,

a = 10.975 (2) Å

b = 12.255 (3) Å

c = 17.741 (4) Å

V = 2386.2 (8) Å3

Z = 4

Mo Kα radiation

μ = 0.31 mm−1

T = 296 K

0.38 × 0.27 × 0.16 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2007 ▶) T min = 0.892, T max = 0.952

12018 measured reflections

4252 independent reflections

2217 reflections with I > 2σ(I)

R int = 0.067

Refinement

R[F 2 > 2σ(F 2)] = 0.053

wR(F 2) = 0.131

S = 1.02

4252 reflections

297 parameters

H-atom parameters constrained

Δρmax = 0.24 e Å−3

Δρmin = −0.16 e Å−3

Absolute structure: Flack (1983 ▶), 1834 Friedel pairs

Flack parameter: 0.01 (10)

Data collection: APEX2 (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEPIII (Burnett & Johnson, 1996 ▶) and ORTEP-3 for Windows (Farrugia, 1997 ▶); software used to prepare material for publication: SHELXTL (Sheldrick, 2008 ▶) and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811010270/dn2666sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811010270/dn2666Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C21H28Cl2N3O6	F(000) = 1028
Mr = 489.36	Dx = 1.362 Mg m−3
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 1127 reflections
a = 10.975 (2) Å	θ = 2.3–16.9°
b = 12.255 (3) Å	µ = 0.31 mm−1
c = 17.741 (4) Å	T = 296 K
V = 2386.2 (8) Å3	Block, blue
Z = 4	0.38 × 0.27 × 0.16 mm

Bruker APEXII CCD diffractometer	4252 independent reflections
Radiation source: fine-focus sealed tube	2217 reflections with I > 2σ(I)
graphite	Rint = 0.067
φ and ω scans	θmax = 25.1°, θmin = 2.0°
Absorption correction: multi-scan (SADABS; Bruker, 2007)	h = −13→12
Tmin = 0.892, Tmax = 0.952	k = −12→14
12018 measured reflections	l = −18→21

Refinement on F2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F2 > 2σ(F2)] = 0.053	w = 1/[σ2(Fo2) + (0.040P)2 + 0.1713P] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.131	(Δ/σ)max < 0.001
S = 1.02	Δρmax = 0.24 e Å−3
4252 reflections	Δρmin = −0.16 e Å−3
297 parameters	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
0 restraints	Extinction coefficient: 0.0025 (7)
Primary atom site location: structure-invariant direct methods	Absolute structure: Flack (1983), 1834 Friedel pairs
Secondary atom site location: difference Fourier map	Flack parameter: 0.01 (10)

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.

	x	y	z	Uiso*/Ueq
Cl1	0.54734 (13)	0.50531 (12)	−0.00306 (8)	0.0831 (5)
Cl2	0.85841 (13)	0.71203 (11)	0.18279 (8)	0.0843 (5)
N1	0.6828 (4)	0.9676 (3)	0.1322 (2)	0.0620 (11)
N2	0.4878 (4)	0.9819 (3)	0.1078 (2)	0.0610 (11)
N3	0.6736 (3)	0.7723 (3)	0.03080 (19)	0.0511 (10)
O1	0.3875 (3)	0.9782 (3)	0.0717 (2)	0.0963 (13)
O2	0.7966 (3)	0.9505 (3)	0.1213 (2)	0.0897 (12)
O3	0.5442 (3)	0.7190 (3)	0.12213 (17)	0.0648 (9)
O4	0.6903 (4)	0.3135 (3)	0.0339 (2)	0.0835 (11)
O5	0.8841 (4)	0.3034 (3)	0.1329 (2)	0.0840 (11)
O6	0.9682 (3)	0.4954 (3)	0.2006 (2)	0.0741 (10)
C1	0.6747 (6)	0.9565 (5)	0.2688 (3)	0.106 (2)
H1A	0.6584	0.8809	0.2591	0.160*
H1B	0.6307	0.9794	0.3128	0.160*
H1C	0.7605	0.9666	0.2769	0.160*
C2	0.6345 (5)	1.0242 (4)	0.2016 (2)	0.0634 (13)
C3	0.6941 (6)	1.1358 (4)	0.2038 (3)	0.104 (2)
H3A	0.7810	1.1274	0.2056	0.157*
H3B	0.6670	1.1745	0.2477	0.157*
H3C	0.6719	1.1760	0.1594	0.157*
C4	0.4234 (6)	0.9421 (6)	0.2350 (4)	0.137 (3)
H4A	0.4187	0.9680	0.2860	0.205*
H4B	0.4643	0.8728	0.2341	0.205*
H4C	0.3427	0.9339	0.2149	0.205*
C5	0.4950 (5)	1.0246 (4)	0.1868 (3)	0.0706 (15)
C6	0.4332 (7)	1.1325 (5)	0.1905 (4)	0.129 (3)
H6A	0.4699	1.1812	0.1547	0.194*
H6B	0.4416	1.1621	0.2403	0.194*
H6C	0.3484	1.1237	0.1788	0.194*
C7	0.5945 (5)	0.9425 (4)	0.0838 (3)	0.0547 (12)
C8	0.6088 (4)	0.8744 (3)	0.0148 (2)	0.0523 (12)
H8	0.5279	0.8571	−0.0053	0.063*
C9	0.6861 (5)	0.9281 (4)	−0.0482 (3)	0.0736 (15)
H9A	0.6349	0.9666	−0.0840	0.088*
H9B	0.7451	0.9786	−0.0273	0.088*
C10	0.7487 (5)	0.8315 (5)	−0.0850 (3)	0.0785 (17)
H10A	0.6946	0.7946	−0.1199	0.094*
H10B	0.8218	0.8540	−0.1116	0.094*
C11	0.7795 (4)	0.7592 (4)	−0.0183 (3)	0.0674 (15)
H11A	0.7893	0.6838	−0.0338	0.081*
H11B	0.8534	0.7835	0.0065	0.081*
C12	0.6345 (4)	0.7020 (4)	0.0830 (3)	0.0527 (12)
C13	0.7062 (4)	0.5988 (4)	0.0917 (3)	0.0496 (11)
C14	0.6708 (4)	0.5020 (4)	0.0577 (2)	0.0594 (12)
C15	0.7333 (5)	0.4047 (4)	0.0686 (3)	0.0593 (14)
C16	0.8309 (5)	0.4042 (4)	0.1181 (3)	0.0604 (13)
C17	0.8696 (4)	0.4979 (4)	0.1537 (2)	0.0546 (11)
C18	0.8091 (5)	0.5945 (4)	0.1389 (3)	0.0565 (12)
C19	0.7769 (6)	0.2553 (6)	−0.0120 (5)	0.133 (3)
H19A	0.8400	0.3044	−0.0280	0.199*
H19B	0.7363	0.2259	−0.0554	0.199*
H19C	0.8121	0.1970	0.0168	0.199*
C20	1.0077 (5)	0.2909 (5)	0.1148 (4)	0.115 (2)
H20A	1.0224	0.3193	0.0652	0.172*
H20B	1.0287	0.2149	0.1160	0.172*
H20C	1.0565	0.3299	0.1507	0.172*
C21	0.9414 (5)	0.4668 (5)	0.2767 (3)	0.106 (2)
H21A	0.8876	0.5202	0.2981	0.159*
H21B	1.0156	0.4644	0.3053	0.159*
H21C	0.9030	0.3964	0.2779	0.159*

	U11	U22	U33	U12	U13	U23
Cl1	0.0821 (9)	0.0807 (9)	0.0865 (10)	0.0042 (8)	−0.0286 (8)	−0.0133 (8)
Cl2	0.0864 (11)	0.0714 (9)	0.0951 (10)	−0.0046 (8)	−0.0274 (9)	−0.0111 (7)
N1	0.049 (3)	0.071 (3)	0.066 (3)	−0.003 (2)	−0.003 (2)	−0.011 (2)
N2	0.049 (3)	0.062 (3)	0.072 (3)	0.003 (2)	−0.006 (2)	−0.024 (2)
N3	0.047 (2)	0.055 (2)	0.052 (2)	0.009 (2)	0.0078 (19)	0.0005 (19)
O1	0.056 (2)	0.103 (3)	0.130 (3)	0.015 (2)	−0.017 (2)	−0.052 (2)
O2	0.054 (2)	0.110 (3)	0.105 (3)	0.001 (2)	−0.014 (2)	−0.015 (2)
O3	0.056 (2)	0.074 (2)	0.065 (2)	0.0052 (19)	0.0137 (19)	0.0060 (18)
O4	0.088 (3)	0.059 (2)	0.103 (3)	−0.005 (2)	−0.010 (2)	−0.013 (2)
O5	0.073 (3)	0.061 (2)	0.118 (3)	0.007 (2)	0.001 (2)	0.018 (2)
O6	0.053 (2)	0.090 (2)	0.079 (3)	0.006 (2)	−0.0084 (19)	0.012 (2)
C1	0.141 (6)	0.108 (5)	0.070 (4)	−0.009 (4)	−0.021 (4)	0.014 (3)
C2	0.085 (4)	0.053 (3)	0.053 (3)	−0.005 (3)	−0.006 (3)	−0.007 (2)
C3	0.145 (6)	0.073 (4)	0.095 (5)	−0.035 (4)	0.014 (4)	−0.013 (3)
C4	0.110 (6)	0.158 (7)	0.142 (6)	−0.001 (5)	0.067 (5)	0.019 (5)
C5	0.089 (4)	0.061 (4)	0.062 (3)	0.010 (3)	0.003 (3)	−0.015 (3)
C6	0.146 (6)	0.113 (5)	0.129 (6)	0.061 (5)	−0.032 (5)	−0.064 (5)
C7	0.050 (3)	0.060 (3)	0.054 (3)	−0.002 (3)	−0.004 (3)	−0.001 (2)
C8	0.051 (3)	0.058 (3)	0.048 (3)	0.004 (2)	−0.004 (2)	−0.006 (2)
C9	0.092 (4)	0.067 (4)	0.062 (3)	0.013 (3)	0.009 (3)	0.006 (3)
C10	0.083 (4)	0.087 (4)	0.065 (4)	0.014 (3)	0.029 (3)	0.011 (3)
C11	0.071 (4)	0.065 (4)	0.066 (4)	0.011 (3)	0.021 (3)	0.007 (3)
C12	0.053 (3)	0.055 (3)	0.050 (3)	0.001 (3)	−0.002 (3)	0.000 (2)
C13	0.045 (3)	0.053 (3)	0.051 (3)	0.002 (2)	0.003 (2)	0.001 (2)
C14	0.056 (3)	0.067 (4)	0.056 (3)	−0.002 (3)	−0.002 (2)	0.003 (3)
C15	0.059 (4)	0.054 (3)	0.065 (3)	−0.010 (3)	0.002 (3)	−0.005 (3)
C16	0.062 (4)	0.049 (3)	0.071 (3)	0.001 (3)	0.005 (3)	0.011 (3)
C17	0.050 (3)	0.055 (3)	0.059 (3)	−0.004 (3)	−0.008 (2)	0.004 (3)
C18	0.061 (3)	0.051 (3)	0.057 (3)	−0.004 (3)	0.001 (3)	0.002 (2)
C19	0.142 (6)	0.124 (6)	0.132 (6)	−0.007 (5)	0.017 (5)	−0.062 (5)
C20	0.070 (4)	0.094 (5)	0.180 (7)	0.017 (4)	−0.001 (4)	0.004 (5)
C21	0.083 (4)	0.157 (6)	0.078 (4)	0.005 (4)	−0.019 (4)	0.026 (4)

Cl1—C14	1.731 (5)	C5—C6	1.487 (7)
Cl2—C18	1.724 (5)	C6—H6A	0.9600
N1—O2	1.281 (5)	C6—H6B	0.9600
N1—C7	1.331 (5)	C6—H6C	0.9600
N1—C2	1.510 (6)	C7—C8	1.490 (6)
N2—O1	1.274 (4)	C8—C9	1.550 (6)
N2—C7	1.336 (5)	C8—H8	0.9800
N2—C5	1.499 (6)	C9—C10	1.516 (6)
N3—C12	1.335 (5)	C9—H9A	0.9700
N3—C11	1.461 (5)	C9—H9B	0.9700
N3—C8	1.468 (5)	C10—C11	1.516 (6)
O3—C12	1.228 (5)	C10—H10A	0.9700
O4—C15	1.359 (5)	C10—H10B	0.9700
O4—C19	1.441 (7)	C11—H11A	0.9700
O5—C16	1.391 (5)	C11—H11B	0.9700
O5—C20	1.403 (6)	C12—C13	1.497 (6)
O6—C17	1.366 (5)	C13—C14	1.387 (6)
O6—C21	1.425 (6)	C13—C18	1.407 (6)
C1—C2	1.517 (6)	C14—C15	1.390 (6)
C1—H1A	0.9600	C15—C16	1.386 (6)
C1—H1B	0.9600	C16—C17	1.377 (6)
C1—H1C	0.9600	C17—C18	1.383 (6)
C2—C3	1.516 (6)	C19—H19A	0.9600
C2—C5	1.554 (7)	C19—H19B	0.9600
C3—H3A	0.9600	C19—H19C	0.9600
C3—H3B	0.9600	C20—H20A	0.9600
C3—H3C	0.9600	C20—H20B	0.9600
C4—C5	1.539 (7)	C20—H20C	0.9600
C4—H4A	0.9600	C21—H21A	0.9600
C4—H4B	0.9600	C21—H21B	0.9600
C4—H4C	0.9600	C21—H21C	0.9600
O2—N1—C7	125.1 (4)	C10—C9—C8	103.1 (4)
O2—N1—C2	122.7 (4)	C10—C9—H9A	111.1
C7—N1—C2	112.1 (4)	C8—C9—H9A	111.1
O1—N2—C7	125.7 (4)	C10—C9—H9B	111.1
O1—N2—C5	121.9 (4)	C8—C9—H9B	111.1
C7—N2—C5	112.2 (4)	H9A—C9—H9B	109.1
C12—N3—C11	126.8 (4)	C11—C10—C9	102.8 (4)
C12—N3—C8	121.9 (4)	C11—C10—H10A	111.2
C11—N3—C8	111.3 (3)	C9—C10—H10A	111.2
C15—O4—C19	115.7 (5)	C11—C10—H10B	111.2
C16—O5—C20	117.4 (4)	C9—C10—H10B	111.2
C17—O6—C21	114.8 (4)	H10A—C10—H10B	109.1
C2—C1—H1A	109.5	N3—C11—C10	103.0 (4)
C2—C1—H1B	109.5	N3—C11—H11A	111.2
H1A—C1—H1B	109.5	C10—C11—H11A	111.2
C2—C1—H1C	109.5	N3—C11—H11B	111.2
H1A—C1—H1C	109.5	C10—C11—H11B	111.2
H1B—C1—H1C	109.5	H11A—C11—H11B	109.1
N1—C2—C1	106.7 (4)	O3—C12—N3	122.9 (4)
N1—C2—C3	106.5 (4)	O3—C12—C13	120.6 (4)
C1—C2—C3	110.3 (4)	N3—C12—C13	116.6 (4)
N1—C2—C5	102.1 (4)	C14—C13—C18	116.9 (4)
C1—C2—C5	114.9 (4)	C14—C13—C12	122.0 (4)
C3—C2—C5	115.3 (4)	C18—C13—C12	121.0 (4)
C2—C3—H3A	109.5	C13—C14—C15	122.4 (4)
C2—C3—H3B	109.5	C13—C14—Cl1	118.0 (4)
H3A—C3—H3B	109.5	C15—C14—Cl1	119.6 (4)
C2—C3—H3C	109.5	O4—C15—C16	123.5 (5)
H3A—C3—H3C	109.5	O4—C15—C14	118.1 (5)
H3B—C3—H3C	109.5	C16—C15—C14	118.3 (4)
C5—C4—H4A	109.5	C17—C16—C15	121.7 (5)
C5—C4—H4B	109.5	C17—C16—O5	121.6 (5)
H4A—C4—H4B	109.5	C15—C16—O5	116.6 (4)
C5—C4—H4C	109.5	O6—C17—C16	120.3 (5)
H4A—C4—H4C	109.5	O6—C17—C18	121.0 (4)
H4B—C4—H4C	109.5	C16—C17—C18	118.6 (4)
C6—C5—N2	109.1 (4)	C17—C18—C13	122.0 (4)
C6—C5—C4	109.1 (5)	C17—C18—Cl2	118.6 (4)
N2—C5—C4	105.3 (5)	C13—C18—Cl2	119.3 (4)
C6—C5—C2	116.4 (5)	O4—C19—H19A	109.5
N2—C5—C2	102.1 (4)	O4—C19—H19B	109.5
C4—C5—C2	114.0 (5)	H19A—C19—H19B	109.5
C5—C6—H6A	109.5	O4—C19—H19C	109.5
C5—C6—H6B	109.5	H19A—C19—H19C	109.5
H6A—C6—H6B	109.5	H19B—C19—H19C	109.5
C5—C6—H6C	109.5	O5—C20—H20A	109.5
H6A—C6—H6C	109.5	O5—C20—H20B	109.5
H6B—C6—H6C	109.5	H20A—C20—H20B	109.5
N1—C7—N2	110.5 (4)	O5—C20—H20C	109.5
N1—C7—C8	125.6 (4)	H20A—C20—H20C	109.5
N2—C7—C8	123.8 (4)	H20B—C20—H20C	109.5
N3—C8—C7	111.7 (4)	O6—C21—H21A	109.5
N3—C8—C9	103.6 (4)	O6—C21—H21B	109.5
C7—C8—C9	114.4 (4)	H21A—C21—H21B	109.5
N3—C8—H8	109.0	O6—C21—H21C	109.5
C7—C8—H8	109.0	H21A—C21—H21C	109.5
C9—C8—H8	109.0	H21B—C21—H21C	109.5
O2—N1—C2—C1	−59.4 (5)	C8—N3—C11—C10	−22.5 (5)
C7—N1—C2—C1	123.1 (5)	C9—C10—C11—N3	37.7 (5)
O2—N1—C2—C3	58.4 (6)	C11—N3—C12—O3	−179.9 (4)
C7—N1—C2—C3	−119.1 (5)	C8—N3—C12—O3	−1.8 (7)
O2—N1—C2—C5	179.6 (4)	C11—N3—C12—C13	−0.4 (6)
C7—N1—C2—C5	2.2 (5)	C8—N3—C12—C13	177.7 (4)
O1—N2—C5—C6	−50.3 (7)	O3—C12—C13—C14	81.7 (6)
C7—N2—C5—C6	134.2 (5)	N3—C12—C13—C14	−97.8 (5)
O1—N2—C5—C4	66.7 (6)	O3—C12—C13—C18	−94.3 (6)
C7—N2—C5—C4	−108.8 (5)	N3—C12—C13—C18	86.2 (5)
O1—N2—C5—C2	−173.9 (4)	C18—C13—C14—C15	−0.5 (7)
C7—N2—C5—C2	10.5 (5)	C12—C13—C14—C15	−176.7 (4)
N1—C2—C5—C6	−125.7 (5)	C18—C13—C14—Cl1	−178.0 (3)
C1—C2—C5—C6	119.3 (5)	C12—C13—C14—Cl1	5.8 (6)
C3—C2—C5—C6	−10.7 (7)	C19—O4—C15—C16	−58.5 (7)
N1—C2—C5—N2	−7.0 (5)	C19—O4—C15—C14	126.1 (6)
C1—C2—C5—N2	−122.1 (4)	C13—C14—C15—O4	178.9 (4)
C3—C2—C5—N2	107.9 (5)	Cl1—C14—C15—O4	−3.6 (6)
N1—C2—C5—C4	105.9 (5)	C13—C14—C15—C16	3.1 (7)
C1—C2—C5—C4	−9.2 (6)	Cl1—C14—C15—C16	−179.3 (4)
C3—C2—C5—C4	−139.1 (5)	O4—C15—C16—C17	−178.3 (4)
O2—N1—C7—N2	−172.9 (5)	C14—C15—C16—C17	−2.8 (7)
C2—N1—C7—N2	4.5 (5)	O4—C15—C16—O5	−1.3 (7)
O2—N1—C7—C8	10.8 (7)	C14—C15—C16—O5	174.2 (4)
C2—N1—C7—C8	−171.8 (4)	C20—O5—C16—C17	−63.0 (7)
O1—N2—C7—N1	174.9 (5)	C20—O5—C16—C15	120.0 (5)
C5—N2—C7—N1	−9.8 (5)	C21—O6—C17—C16	−86.5 (6)
O1—N2—C7—C8	−8.7 (8)	C21—O6—C17—C18	95.5 (5)
C5—N2—C7—C8	166.6 (4)	C15—C16—C17—O6	−178.2 (4)
C12—N3—C8—C7	56.3 (5)	O5—C16—C17—O6	4.9 (7)
C11—N3—C8—C7	−125.3 (4)	C15—C16—C17—C18	−0.2 (7)
C12—N3—C8—C9	179.9 (4)	O5—C16—C17—C18	−177.1 (4)
C11—N3—C8—C9	−1.7 (5)	O6—C17—C18—C13	−178.9 (4)
N1—C7—C8—N3	48.9 (6)	C16—C17—C18—C13	3.1 (7)
N2—C7—C8—N3	−127.0 (5)	O6—C17—C18—Cl2	−1.5 (6)
N1—C7—C8—C9	−68.5 (6)	C16—C17—C18—Cl2	−179.5 (4)
N2—C7—C8—C9	115.6 (5)	C14—C13—C18—C17	−2.7 (7)
N3—C8—C9—C10	25.2 (5)	C12—C13—C18—C17	173.5 (4)
C7—C8—C9—C10	147.1 (4)	C14—C13—C18—Cl2	179.8 (3)
C8—C9—C10—C11	−38.9 (5)	C12—C13—C18—Cl2	−3.9 (6)
C12—N3—C11—C10	155.8 (4)

Cg3 is the centroid of the C13–C18 ring.

D—H···A	D—H	H···A	D···A	D—H···A
C6—H6B···O3i	0.96	2.54	3.498 (8)	173
C11—H11A···O1ii	0.97	2.36	3.281 (6)	159
C21—H21B···O2iii	0.96	2.44	3.403 (6)	178
C4—H4A···Cg3i	0.96	2.86	3.619 (7)	136

Table 1

Hydrogen-bond geometry (Å, °)

Cg3 is the centroid of the C13–C18 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C6—H6B⋯O3i	0.96	2.54	3.498 (8)	173
C11—H11A⋯O1ii	0.97	2.36	3.281 (6)	159
C21—H21B⋯O2iii	0.96	2.44	3.403 (6)	178
C4—H4A⋯Cg3i	0.96	2.86	3.619 (7)	136

Symmetry codes: (i) ; (ii) ; (iii) .