10-(4-Chloro-phen-yl)-9-(4-fluoro-phen-yl)-3,3,6,6-tetra-methyl-3,4,6,7,9,10-hexa-hydro-acridine-1,8(2H,5H)-dione.

The title compound, C(29)H(29)ClFNO(2), was synthesized by the reaction of 4-fluoro-benzaldehyde, 5,5-dimethyl-cyclo-hexane-1,3-dione and 3-(4-chloro-phenyl-amino)-5,5-dimethyl-cyclo-hex-2-enone in an ionic liquid (1-butyl-3-methyl-imidazolium bromide). X-ray analysis reveals that the 1,4-dihydro-pyridine ring adopts a boat conformation, while each of the attached partially saturated six-membered rings adopts a half-chair conformation. The structure is stabilized by weak C-H⋯O and C-H⋯F hydrogen bonds. The mol-ecule has approximate mirror symmetry; the largest deviation from this symmetry concerns the fluoro- and chloro-phenyl rings.

Related literature

For related literature, see: Dzierzbicka et al. (2001 ▶); Hutchins et al. (2003 ▶); Kamal et al. (2004 ▶); Li et al. (2003 ▶); Petříček et al. (2000 ▶); Srivastava & Nizamuddin (2004 ▶); Wang et al. (2002 ▶, 2003 ▶).

Experimental

Crystal data

C29H29ClFNO2

M = 477.98

Monoclinic,

a = 12.0985 (12) Å

b = 10.9001 (10) Å

c = 19.4724 (18) Å

β = 101.231 (3)°

V = 2518.7 (4) Å3

Z = 4

Mo Kα radiation

μ = 0.18 mm−1

T = 113 (2) K

0.32 × 0.20 × 0.18 mm

Data collection

Rigaku Saturn diffractometer

Absorption correction: multi-scan (CrystalClear; Rigaku, 1999 ▶) T min = 0.943, T max = 0.967

30908 measured reflections

6016 independent reflections

5436 reflections with I > 2σ(I)

R int = 0.040

Refinement

R[F 2 > 2σ(F 2)] = 0.055

wR(F 2) = 0.137

S = 1.10

6016 reflections

312 parameters

H-atom parameters constrained

Δρmax = 0.42 e Å−3

Δρmin = −0.45 e Å−3

Data collection: CrystalClear (Rigaku, 1999 ▶); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: CrystalStructure (Rigaku/MSC, 2003 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808025695/fb2102sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808025695/fb2102Isup2.hkl

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

C29H29ClFNO2	F000 = 1008
Mr = 477.98	Dx = 1.260 Mg m−3
Monoclinic, P21/c	Melting point = 583–585 K
Hall symbol: -P 2ybc	Mo Kα radiation λ = 0.71070 Å
a = 12.0985 (12) Å	Cell parameters from 8097 reflections
b = 10.9001 (10) Å	θ = 1.7–27.9º
c = 19.4724 (18) Å	µ = 0.19 mm−1
β = 101.231 (3)º	T = 113 (2) K
V = 2518.7 (4) Å3	Block, yellow
Z = 4	0.32 × 0.20 × 0.18 mm

Rigaku Saturn diffractometer	6016 independent reflections
Radiation source: rotating anode	5436 reflections with I > 2σ(I)
Monochromator: confocal	Rint = 0.040
Detector resolution: 14.63 pixels mm-1	θmax = 27.9º
T = 113(2) K	θmin = 1.7º
ω scans	h = −15→15
Absorption correction: multi-scan(CrystalClear; Rigaku, 1999)	k = −14→14
Tmin = 0.943, Tmax = 0.967	l = −25→25
30908 measured reflections

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.055	H-atom parameters constrained
wR(F2) = 0.137	w = 1/[σ2(Fo2) + (0.0579P)2 + 1.0431P] where P = (Fo2 + 2Fc2)/3
S = 1.10	(Δ/σ)max = 0.001
6016 reflections	Δρmax = 0.42 e Å−3
312 parameters	Δρmin = −0.45 e Å−3
112 constraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0058 (9)

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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	0.86649 (5)	1.04288 (4)	0.25315 (3)	0.04213 (16)
F1	1.03322 (14)	0.02721 (16)	0.07820 (8)	0.0761 (5)
O1	0.56729 (11)	0.16766 (11)	0.17692 (7)	0.0326 (3)
O2	0.57270 (11)	0.31474 (12)	−0.06509 (7)	0.0330 (3)
N1	0.70646 (12)	0.56013 (12)	0.13279 (7)	0.0229 (3)
C1	0.67413 (13)	0.47215 (14)	0.17771 (8)	0.0219 (3)
C2	0.64094 (13)	0.35886 (15)	0.15353 (8)	0.0223 (3)
C3	0.64825 (14)	0.31701 (14)	0.08070 (9)	0.0231 (3)
H3	0.5793	0.2681	0.0614	0.028*
C4	0.65130 (13)	0.42790 (15)	0.03444 (9)	0.0231 (3)
C5	0.68642 (13)	0.53925 (14)	0.06063 (9)	0.0224 (3)
C6	0.74535 (14)	0.67913 (14)	0.16009 (8)	0.0228 (3)
C7	0.85853 (15)	0.69498 (17)	0.18908 (10)	0.0304 (4)
H7	0.9099	0.6289	0.1895	0.036*
C8	0.89647 (16)	0.80758 (18)	0.21746 (10)	0.0336 (4)
H8	0.9738	0.8194	0.2376	0.040*
C9	0.82031 (15)	0.90184 (16)	0.21587 (9)	0.0278 (4)
C10	0.70815 (15)	0.88861 (15)	0.18595 (9)	0.0269 (4)
H10	0.6576	0.9557	0.1844	0.032*
C11	0.67004 (14)	0.77543 (15)	0.15803 (9)	0.0244 (3)
H11	0.5927	0.7642	0.1376	0.029*
C12	0.67473 (15)	0.51183 (15)	0.25200 (9)	0.0263 (4)
H12A	0.6074	0.5631	0.2527	0.032*
H12B	0.7422	0.5631	0.2686	0.032*
C13	0.67515 (15)	0.40361 (15)	0.30251 (9)	0.0264 (4)
C14	0.58278 (15)	0.31382 (16)	0.26947 (9)	0.0274 (4)
H14A	0.5842	0.2417	0.3006	0.033*
H14B	0.5085	0.3541	0.2656	0.033*
C15	0.59618 (13)	0.27108 (15)	0.19831 (9)	0.0242 (3)
C16	0.65091 (19)	0.45153 (17)	0.37181 (10)	0.0365 (4)
H16A	0.5787	0.4952	0.3632	0.055*
H16B	0.7111	0.5077	0.3931	0.055*
H16C	0.6474	0.3825	0.4035	0.055*
C17	0.78922 (16)	0.33872 (18)	0.31572 (11)	0.0367 (4)
H17A	0.8487	0.3977	0.3342	0.055*
H17B	0.8031	0.3043	0.2717	0.055*
H17C	0.7890	0.2725	0.3497	0.055*
C18	0.70364 (15)	0.64547 (15)	0.01412 (9)	0.0263 (4)
H18A	0.7669	0.6965	0.0386	0.032*
H18B	0.6350	0.6970	0.0056	0.032*
C19	0.72913 (15)	0.60365 (16)	−0.05647 (9)	0.0276 (4)
C20	0.63778 (15)	0.51338 (17)	−0.08888 (9)	0.0293 (4)
H20A	0.5663	0.5589	−0.1036	0.035*
H20B	0.6584	0.4777	−0.1314	0.035*
C21	0.61825 (14)	0.41026 (16)	−0.04108 (9)	0.0264 (4)
C22	0.84573 (16)	0.54320 (18)	−0.04596 (10)	0.0338 (4)
H22A	0.8465	0.4697	−0.0168	0.051*
H22B	0.9029	0.6011	−0.0228	0.051*
H22C	0.8622	0.5201	−0.0916	0.051*
C23	0.72650 (17)	0.71613 (17)	−0.10400 (10)	0.0347 (4)
H23A	0.7434	0.6909	−0.1491	0.052*
H23B	0.7829	0.7758	−0.0818	0.052*
H23C	0.6515	0.7537	−0.1114	0.052*
C24	0.75157 (15)	0.23635 (15)	0.08100 (9)	0.0262 (4)
C25	0.85885 (16)	0.28331 (19)	0.10536 (10)	0.0350 (4)
H25	0.8671	0.3649	0.1227	0.042*
C26	0.95412 (18)	0.2128 (2)	0.10467 (11)	0.0443 (5)
H26	1.0274	0.2449	0.1214	0.053*
C27	0.9395 (2)	0.0961 (2)	0.07926 (11)	0.0480 (6)
C28	0.8360 (2)	0.0456 (2)	0.05529 (11)	0.0479 (6)
H28	0.8289	−0.0363	0.0382	0.057*
C29	0.74091 (18)	0.11699 (17)	0.05649 (10)	0.0357 (4)
H29	0.6680	0.0834	0.0403	0.043*

	U11	U22	U33	U12	U13	U23
Cl1	0.0539 (3)	0.0306 (3)	0.0401 (3)	−0.0193 (2)	0.0050 (2)	−0.00797 (19)
F1	0.0758 (10)	0.1001 (13)	0.0550 (9)	0.0666 (10)	0.0195 (8)	0.0108 (8)
O1	0.0356 (7)	0.0234 (6)	0.0404 (7)	−0.0077 (5)	0.0110 (6)	−0.0044 (5)
O2	0.0345 (7)	0.0322 (7)	0.0303 (7)	−0.0003 (5)	0.0012 (5)	−0.0087 (5)
N1	0.0274 (7)	0.0189 (6)	0.0234 (7)	−0.0022 (5)	0.0071 (5)	−0.0024 (5)
C1	0.0220 (8)	0.0207 (8)	0.0236 (8)	0.0005 (6)	0.0060 (6)	−0.0010 (6)
C2	0.0210 (8)	0.0212 (8)	0.0255 (8)	0.0014 (6)	0.0062 (6)	−0.0019 (6)
C3	0.0240 (8)	0.0199 (8)	0.0255 (8)	−0.0012 (6)	0.0051 (6)	−0.0040 (6)
C4	0.0214 (8)	0.0228 (8)	0.0249 (8)	0.0013 (6)	0.0042 (6)	−0.0019 (6)
C5	0.0215 (8)	0.0215 (8)	0.0248 (8)	0.0021 (6)	0.0058 (6)	−0.0007 (6)
C6	0.0272 (8)	0.0195 (8)	0.0225 (8)	−0.0033 (6)	0.0069 (6)	−0.0011 (6)
C7	0.0247 (9)	0.0297 (9)	0.0361 (10)	0.0017 (7)	0.0042 (7)	0.0027 (7)
C8	0.0251 (9)	0.0359 (10)	0.0374 (10)	−0.0087 (7)	0.0000 (7)	0.0017 (8)
C9	0.0338 (9)	0.0255 (8)	0.0242 (8)	−0.0101 (7)	0.0058 (7)	−0.0005 (7)
C10	0.0297 (9)	0.0215 (8)	0.0310 (9)	−0.0012 (7)	0.0093 (7)	−0.0027 (7)
C11	0.0231 (8)	0.0227 (8)	0.0281 (8)	−0.0023 (6)	0.0065 (6)	−0.0025 (6)
C12	0.0355 (9)	0.0201 (8)	0.0248 (8)	−0.0015 (7)	0.0097 (7)	−0.0032 (6)
C13	0.0335 (9)	0.0199 (8)	0.0253 (8)	−0.0007 (7)	0.0046 (7)	−0.0001 (6)
C14	0.0311 (9)	0.0244 (8)	0.0282 (9)	−0.0023 (7)	0.0091 (7)	0.0014 (7)
C15	0.0203 (8)	0.0207 (8)	0.0314 (9)	0.0002 (6)	0.0044 (6)	−0.0022 (6)
C16	0.0572 (13)	0.0263 (9)	0.0267 (9)	−0.0019 (8)	0.0100 (8)	0.0006 (7)
C17	0.0349 (10)	0.0314 (10)	0.0394 (11)	0.0016 (8)	−0.0038 (8)	−0.0039 (8)
C18	0.0303 (9)	0.0230 (8)	0.0268 (9)	0.0019 (7)	0.0084 (7)	0.0003 (7)
C19	0.0307 (9)	0.0282 (9)	0.0249 (8)	0.0044 (7)	0.0081 (7)	0.0028 (7)
C20	0.0307 (9)	0.0318 (9)	0.0243 (8)	0.0053 (7)	0.0028 (7)	0.0005 (7)
C21	0.0217 (8)	0.0286 (9)	0.0283 (9)	0.0059 (7)	0.0039 (6)	−0.0034 (7)
C22	0.0292 (9)	0.0388 (10)	0.0356 (10)	0.0058 (8)	0.0121 (8)	0.0053 (8)
C23	0.0415 (11)	0.0330 (10)	0.0309 (10)	0.0053 (8)	0.0106 (8)	0.0067 (8)
C24	0.0332 (9)	0.0248 (8)	0.0221 (8)	0.0069 (7)	0.0096 (7)	0.0026 (6)
C25	0.0299 (10)	0.0371 (10)	0.0395 (11)	0.0063 (8)	0.0107 (8)	0.0043 (8)
C26	0.0334 (11)	0.0602 (14)	0.0423 (12)	0.0169 (10)	0.0146 (9)	0.0142 (10)
C27	0.0546 (14)	0.0618 (15)	0.0310 (10)	0.0382 (12)	0.0168 (9)	0.0116 (10)
C28	0.0770 (17)	0.0372 (11)	0.0303 (11)	0.0299 (11)	0.0124 (10)	−0.0012 (8)
C29	0.0515 (12)	0.0278 (9)	0.0273 (9)	0.0104 (8)	0.0058 (8)	−0.0018 (7)

Cl1—C9	1.7449 (18)	C14—H14A	0.9900
F1—C27	1.364 (2)	C14—H14B	0.9900
O1—C15	1.229 (2)	C16—H16A	0.9800
O2—C21	1.227 (2)	C16—H16B	0.9800
N1—C5	1.397 (2)	C16—H16C	0.9800
N1—C1	1.404 (2)	C17—H17A	0.9800
N1—C6	1.445 (2)	C17—H17B	0.9800
C1—C2	1.354 (2)	C17—H17C	0.9800
C1—C12	1.509 (2)	C18—C19	1.535 (2)
C2—C15	1.467 (2)	C18—H18A	0.9900
C2—C3	1.509 (2)	C18—H18B	0.9900
C3—C4	1.512 (2)	C19—C20	1.522 (3)
C3—C24	1.527 (2)	C19—C23	1.533 (2)
C3—H3	1.0000	C19—C22	1.534 (2)
C4—C5	1.353 (2)	C20—C21	1.507 (3)
C4—C21	1.460 (2)	C20—H20A	0.9900
C5—C18	1.509 (2)	C20—H20B	0.9900
C6—C11	1.385 (2)	C22—H22A	0.9800
C6—C7	1.387 (2)	C22—H22B	0.9800
C7—C8	1.387 (3)	C22—H22C	0.9800
C7—H7	0.9500	C23—H23A	0.9800
C8—C9	1.376 (3)	C23—H23B	0.9800
C8—H8	0.9500	C23—H23C	0.9800
C9—C10	1.376 (2)	C24—C29	1.383 (2)
C10—C11	1.390 (2)	C24—C25	1.390 (3)
C10—H10	0.9500	C25—C26	1.388 (3)
C11—H11	0.9500	C25—H25	0.9500
C12—C13	1.535 (2)	C26—C27	1.364 (3)
C12—H12A	0.9900	C26—H26	0.9500
C12—H12B	0.9900	C27—C28	1.364 (4)
C13—C17	1.527 (2)	C28—C29	1.393 (3)
C13—C16	1.528 (2)	C28—H28	0.9500
C13—C14	1.530 (2)	C29—H29	0.9500
C14—C15	1.500 (2)
C5—N1—C1	120.03 (13)	H16A—C16—H16B	109.5
C5—N1—C6	119.75 (13)	C13—C16—H16C	109.5
C1—N1—C6	119.62 (13)	H16A—C16—H16C	109.5
C2—C1—N1	120.39 (15)	H16B—C16—H16C	109.5
C2—C1—C12	122.73 (15)	C13—C17—H17A	109.5
N1—C1—C12	116.85 (13)	C13—C17—H17B	109.5
C1—C2—C15	120.44 (15)	H17A—C17—H17B	109.5
C1—C2—C3	122.33 (15)	C13—C17—H17C	109.5
C15—C2—C3	117.23 (14)	H17A—C17—H17C	109.5
C2—C3—C4	109.33 (13)	H17B—C17—H17C	109.5
C2—C3—C24	111.60 (13)	C5—C18—C19	112.63 (14)
C4—C3—C24	110.34 (13)	C5—C18—H18A	109.1
C2—C3—H3	108.5	C19—C18—H18A	109.1
C4—C3—H3	108.5	C5—C18—H18B	109.1
C24—C3—H3	108.5	C19—C18—H18B	109.1
C5—C4—C21	120.15 (15)	H18A—C18—H18B	107.8
C5—C4—C3	122.35 (15)	C20—C19—C23	109.80 (15)
C21—C4—C3	117.47 (14)	C20—C19—C22	110.63 (15)
C4—C5—N1	120.36 (15)	C23—C19—C22	109.55 (15)
C4—C5—C18	122.15 (15)	C20—C19—C18	107.87 (14)
N1—C5—C18	117.48 (14)	C23—C19—C18	108.60 (14)
C11—C6—C7	120.61 (15)	C22—C19—C18	110.36 (14)
C11—C6—N1	120.28 (14)	C21—C20—C19	114.50 (14)
C7—C6—N1	119.11 (15)	C21—C20—H20A	108.6
C6—C7—C8	119.77 (17)	C19—C20—H20A	108.6
C6—C7—H7	120.1	C21—C20—H20B	108.6
C8—C7—H7	120.1	C19—C20—H20B	108.6
C9—C8—C7	118.91 (16)	H20A—C20—H20B	107.6
C9—C8—H8	120.5	O2—C21—C4	120.67 (16)
C7—C8—H8	120.5	O2—C21—C20	120.69 (16)
C10—C9—C8	122.13 (16)	C4—C21—C20	118.61 (15)
C10—C9—Cl1	118.55 (14)	C19—C22—H22A	109.5
C8—C9—Cl1	119.32 (14)	C19—C22—H22B	109.5
C9—C10—C11	118.90 (16)	H22A—C22—H22B	109.5
C9—C10—H10	120.6	C19—C22—H22C	109.5
C11—C10—H10	120.6	H22A—C22—H22C	109.5
C6—C11—C10	119.66 (15)	H22B—C22—H22C	109.5
C6—C11—H11	120.2	C19—C23—H23A	109.5
C10—C11—H11	120.2	C19—C23—H23B	109.5
C1—C12—C13	113.13 (13)	H23A—C23—H23B	109.5
C1—C12—H12A	109.0	C19—C23—H23C	109.5
C13—C12—H12A	109.0	H23A—C23—H23C	109.5
C1—C12—H12B	109.0	H23B—C23—H23C	109.5
C13—C12—H12B	109.0	C29—C24—C25	118.83 (17)
H12A—C12—H12B	107.8	C29—C24—C3	121.26 (16)
C17—C13—C16	109.41 (15)	C25—C24—C3	119.90 (15)
C17—C13—C14	109.67 (14)	C26—C25—C24	121.0 (2)
C16—C13—C14	109.88 (15)	C26—C25—H25	119.5
C17—C13—C12	110.72 (15)	C24—C25—H25	119.5
C16—C13—C12	109.02 (14)	C27—C26—C25	118.1 (2)
C14—C13—C12	108.12 (14)	C27—C26—H26	121.0
C15—C14—C13	112.68 (14)	C25—C26—H26	121.0
C15—C14—H14A	109.1	F1—C27—C26	118.0 (2)
C13—C14—H14A	109.1	F1—C27—C28	118.9 (2)
C15—C14—H14B	109.1	C26—C27—C28	123.11 (19)
C13—C14—H14B	109.1	C27—C28—C29	118.3 (2)
H14A—C14—H14B	107.8	C27—C28—H28	120.8
O1—C15—C2	120.69 (16)	C29—C28—H28	120.8
O1—C15—C14	121.55 (15)	C24—C29—C28	120.6 (2)
C2—C15—C14	117.72 (14)	C24—C29—H29	119.7
C13—C16—H16A	109.5	C28—C29—H29	119.7
C13—C16—H16B	109.5
C5—N1—C1—C2	11.0 (2)	C1—C12—C13—C17	71.36 (18)
C6—N1—C1—C2	−177.87 (14)	C1—C12—C13—C16	−168.23 (15)
C5—N1—C1—C12	−166.96 (14)	C1—C12—C13—C14	−48.81 (19)
C6—N1—C1—C12	4.1 (2)	C17—C13—C14—C15	−64.45 (19)
N1—C1—C2—C15	−173.71 (14)	C16—C13—C14—C15	175.25 (14)
C12—C1—C2—C15	4.2 (2)	C12—C13—C14—C15	56.38 (19)
N1—C1—C2—C3	6.5 (2)	C1—C2—C15—O1	−179.08 (15)
C12—C1—C2—C3	−175.64 (15)	C3—C2—C15—O1	0.7 (2)
C1—C2—C3—C4	−22.1 (2)	C1—C2—C15—C14	3.3 (2)
C15—C2—C3—C4	158.08 (14)	C3—C2—C15—C14	−176.84 (14)
C1—C2—C3—C24	100.24 (18)	C13—C14—C15—O1	147.61 (16)
C15—C2—C3—C24	−79.58 (18)	C13—C14—C15—C2	−34.8 (2)
C2—C3—C4—C5	23.5 (2)	C4—C5—C18—C19	−25.5 (2)
C24—C3—C4—C5	−99.62 (18)	N1—C5—C18—C19	155.53 (14)
C2—C3—C4—C21	−158.60 (14)	C5—C18—C19—C20	52.13 (18)
C24—C3—C4—C21	78.30 (18)	C5—C18—C19—C23	171.08 (15)
C21—C4—C5—N1	173.05 (14)	C5—C18—C19—C22	−68.83 (19)
C3—C4—C5—N1	−9.1 (2)	C23—C19—C20—C21	−169.46 (14)
C21—C4—C5—C18	−5.9 (2)	C22—C19—C20—C21	69.51 (19)
C3—C4—C5—C18	171.93 (15)	C18—C19—C20—C21	−51.28 (19)
C1—N1—C5—C4	−9.7 (2)	C5—C4—C21—O2	−170.52 (16)
C6—N1—C5—C4	179.21 (15)	C3—C4—C21—O2	11.5 (2)
C1—N1—C5—C18	169.32 (14)	C5—C4—C21—C20	7.5 (2)
C6—N1—C5—C18	−1.8 (2)	C3—C4—C21—C20	−170.44 (14)
C5—N1—C6—C11	79.2 (2)	C19—C20—C21—O2	−159.05 (16)
C1—N1—C6—C11	−91.90 (19)	C19—C20—C21—C4	22.9 (2)
C5—N1—C6—C7	−101.61 (19)	C2—C3—C24—C29	120.14 (17)
C1—N1—C6—C7	87.3 (2)	C4—C3—C24—C29	−118.09 (17)
C11—C6—C7—C8	1.2 (3)	C2—C3—C24—C25	−60.7 (2)
N1—C6—C7—C8	−177.99 (16)	C4—C3—C24—C25	61.0 (2)
C6—C7—C8—C9	−0.3 (3)	C29—C24—C25—C26	0.6 (3)
C7—C8—C9—C10	−1.2 (3)	C3—C24—C25—C26	−178.51 (17)
C7—C8—C9—Cl1	178.58 (14)	C24—C25—C26—C27	0.1 (3)
C8—C9—C10—C11	1.7 (3)	C25—C26—C27—F1	179.58 (18)
Cl1—C9—C10—C11	−178.07 (13)	C25—C26—C27—C28	−0.7 (3)
C7—C6—C11—C10	−0.7 (3)	F1—C27—C28—C29	−179.85 (18)
N1—C6—C11—C10	178.50 (15)	C26—C27—C28—C29	0.4 (3)
C9—C10—C11—C6	−0.7 (3)	C25—C24—C29—C28	−0.9 (3)
C2—C1—C12—C13	20.1 (2)	C3—C24—C29—C28	178.23 (16)
N1—C1—C12—C13	−161.93 (14)	C27—C28—C29—C24	0.4 (3)

D—H···A	D—H	H···A	D···A	D—H···A
C16—H16C···O2i	0.98	2.45	3.359 (2)	153
C11—H11···O2ii	0.95	2.37	3.286 (2)	160
C10—H10···O1iii	0.95	2.55	3.474 (2)	165
C16—H16A···O1iv	0.98	2.59	3.528 (2)	159
C17—H17A···F1v	0.98	2.45	3.373 (2)	157

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C16—H16C⋯O2i	0.98	2.45	3.359 (2)	153
C11—H11⋯O2ii	0.95	2.37	3.286 (2)	160
C10—H10⋯O1iii	0.95	2.55	3.474 (2)	165
C16—H16A⋯O1iv	0.98	2.59	3.528 (2)	159
C17—H17A⋯F1v	0.98	2.45	3.373 (2)	157

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