1'-Methyl-4'-[4-(trifluoro-meth-yl)phen-yl]dispiro-[acenaphthyl-ene-1,2'-pyrrolidine-3',2''-indane]-2,1''(1H)-dione.

In the title compound, C(31)H(22)F(3)NO(2), the pyrrolidine and cyclo-pentane rings within the dihydro-indene ring system are in envelope conformations, with the N atom and the spiro-C atom at the flap, respectively. An intra-molecular C-H⋯O hydrogen bond forms an S(8) ring motif. The mean plane through the pyrrolidine ring [r.m.s. deviation = 0.179 (2) Å] makes dihedral angles of 86.30 (13), 88.99 (10) and 79.69 (11)° with the benzene ring, the dihydro-acenaphthyl-ene ring and the mean plane of the indane system, respectively. In the crystal, mol-ecules are linked by C-H⋯O and C-H⋯N hydrogen bonds into a two-dimensional network parallel to the ac plane. C-H⋯π inter-actions further stabilize the crystal structure.

Related literature

For the structures of related heterocyclic compounds with anti­tubercular activity, see: Wei, Ali, Choon et al. (2011 ▶, 2012 ▶); Wei, Ali, Ismail et al. (2011 ▶). For ring conformations, see: Cremer & Pople (1975 ▶). For hydrogen-bond motifs, see: Bernstein et al. (1995 ▶). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986 ▶).

Experimental

Crystal data

C31H22F3NO2

M = 497.50

Monoclinic,

a = 8.8373 (2) Å

b = 20.1333 (5) Å

c = 13.7129 (3) Å

β = 96.243 (1)°

V = 2425.39 (10) Å3

Z = 4

Mo Kα radiation

μ = 0.10 mm−1

T = 100 K

0.30 × 0.28 × 0.20 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.971, T max = 0.980

27133 measured reflections

7039 independent reflections

4753 reflections with I > 2σ(I)

R int = 0.072

Refinement

R[F 2 > 2σ(F 2)] = 0.082

wR(F 2) = 0.186

S = 1.10

7039 reflections

335 parameters

H-atom parameters constrained

Δρmax = 0.55 e Å−3

Δρmin = −0.37 e Å−3

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812013645/rz2729sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812013645/rz2729Isup2.hkl

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

C31H22F3NO2	F(000) = 1032
Mr = 497.50	Dx = 1.362 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 5213 reflections
a = 8.8373 (2) Å	θ = 2.5–30.1°
b = 20.1333 (5) Å	µ = 0.10 mm−1
c = 13.7129 (3) Å	T = 100 K
β = 96.243 (1)°	Block, yellow
V = 2425.39 (10) Å3	0.30 × 0.28 × 0.20 mm
Z = 4

Bruker SMART APEXII CCD area-detector diffractometer	7039 independent reflections
Radiation source: fine-focus sealed tube	4753 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.072
φ and ω scans	θmax = 30.1°, θmin = 2.0°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −10→12
Tmin = 0.971, Tmax = 0.980	k = −28→23
27133 measured reflections	l = −19→19

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.082	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.186	H-atom parameters constrained
S = 1.10	w = 1/[σ2(Fo2) + (0.062P)2 + 2.6644P] where P = (Fo2 + 2Fc2)/3
7039 reflections	(Δ/σ)max < 0.001
335 parameters	Δρmax = 0.55 e Å−3
0 restraints	Δρmin = −0.37 e Å−3

Experimental. The crystal was placed in the cold stream of an Oxford Cryosystems Cobra open-flow nitrogen cryostat (Cosier & Glazer, 1986) operating at 100.0 (1) K.

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
F1	0.0010 (2)	0.42817 (7)	0.71415 (11)	0.0310 (4)
F2	0.0624 (2)	0.49747 (9)	0.82994 (11)	0.0382 (5)
F3	−0.1474 (2)	0.50882 (9)	0.73716 (14)	0.0416 (5)
O1	0.6473 (2)	0.62588 (9)	0.59831 (12)	0.0197 (4)
O2	0.2586 (2)	0.76005 (9)	0.33429 (12)	0.0218 (4)
N1	0.5391 (2)	0.65334 (10)	0.38454 (14)	0.0159 (4)
C1	0.6585 (3)	0.67919 (12)	0.55815 (16)	0.0149 (5)
C2	0.7746 (3)	0.73053 (12)	0.58287 (16)	0.0159 (5)
C3	0.8914 (3)	0.73588 (13)	0.65826 (17)	0.0189 (5)
H3A	0.9055	0.7031	0.7083	0.023*
C4	0.9887 (3)	0.79137 (13)	0.65863 (18)	0.0220 (6)
H4A	1.0681	0.7963	0.7107	0.026*
C5	0.9720 (3)	0.83884 (13)	0.58523 (17)	0.0206 (5)
H5A	1.0404	0.8754	0.5877	0.025*
C6	0.8547 (3)	0.83393 (12)	0.50641 (17)	0.0181 (5)
C7	0.8279 (3)	0.87667 (13)	0.42369 (18)	0.0218 (5)
H7A	0.8897	0.9149	0.4186	0.026*
C8	0.7125 (3)	0.86261 (13)	0.35127 (17)	0.0212 (5)
H8A	0.6971	0.8913	0.2961	0.025*
C9	0.6154 (3)	0.80682 (13)	0.35583 (16)	0.0196 (5)
H9A	0.5375	0.7981	0.3040	0.024*
C10	0.6352 (3)	0.76561 (12)	0.43570 (16)	0.0151 (5)
C11	0.7565 (3)	0.77944 (12)	0.50919 (16)	0.0162 (5)
C12	0.5532 (3)	0.70278 (11)	0.46338 (15)	0.0146 (5)
C13	0.3835 (3)	0.71004 (12)	0.48642 (16)	0.0151 (5)
C14	0.3684 (3)	0.73745 (12)	0.59096 (16)	0.0162 (5)
H14A	0.2760	0.7198	0.6167	0.019*
H14B	0.4586	0.7256	0.6369	0.019*
C15	0.3574 (3)	0.81157 (12)	0.57692 (16)	0.0171 (5)
C16	0.3775 (3)	0.86177 (13)	0.64670 (18)	0.0201 (5)
H16A	0.4036	0.8516	0.7141	0.024*
C17	0.3584 (3)	0.92734 (13)	0.61549 (19)	0.0233 (6)
H17A	0.3737	0.9622	0.6622	0.028*
C18	0.3172 (3)	0.94303 (13)	0.5170 (2)	0.0264 (6)
H18A	0.3039	0.9881	0.4976	0.032*
C19	0.2956 (3)	0.89312 (13)	0.44737 (18)	0.0222 (5)
H19A	0.2663	0.9032	0.3803	0.027*
C20	0.3181 (3)	0.82781 (12)	0.47853 (16)	0.0164 (5)
C21	0.3106 (3)	0.76631 (12)	0.41957 (16)	0.0159 (5)
C22	0.3086 (3)	0.64178 (12)	0.45501 (16)	0.0165 (5)
H22A	0.2291	0.6511	0.3991	0.020*
C23	0.4350 (3)	0.60207 (12)	0.41273 (17)	0.0182 (5)
H23A	0.4869	0.5719	0.4627	0.022*
H23B	0.3934	0.5756	0.3551	0.022*
C24	0.2298 (3)	0.60506 (12)	0.53182 (17)	0.0167 (5)
C25	0.0724 (3)	0.60120 (13)	0.52232 (18)	0.0197 (5)
H25A	0.0153	0.6231	0.4690	0.024*
C26	−0.0042 (3)	0.56580 (13)	0.58934 (19)	0.0225 (5)
H26A	−0.1121	0.5631	0.5812	0.027*
C27	0.0790 (3)	0.53456 (12)	0.66806 (17)	0.0187 (5)
C28	0.2365 (3)	0.53925 (12)	0.68008 (17)	0.0199 (5)
H28A	0.2929	0.5187	0.7349	0.024*
C29	0.3123 (3)	0.57388 (12)	0.61240 (17)	0.0198 (5)
H29A	0.4202	0.5765	0.6207	0.024*
C30	0.6816 (3)	0.62840 (13)	0.35438 (18)	0.0225 (6)
H30A	0.6606	0.6025	0.2940	0.034*
H30B	0.7321	0.6001	0.4063	0.034*
H30C	0.7481	0.6659	0.3426	0.034*
C31	−0.0011 (3)	0.49303 (13)	0.73694 (18)	0.0217 (5)

	U11	U22	U33	U12	U13	U23
F1	0.0516 (11)	0.0162 (8)	0.0285 (8)	−0.0061 (7)	0.0187 (7)	−0.0013 (6)
F2	0.0565 (12)	0.0422 (10)	0.0176 (7)	−0.0214 (9)	0.0121 (7)	−0.0018 (7)
F3	0.0346 (10)	0.0408 (11)	0.0548 (11)	0.0048 (8)	0.0291 (9)	0.0143 (9)
O1	0.0204 (9)	0.0198 (9)	0.0192 (8)	−0.0005 (7)	0.0044 (7)	0.0053 (7)
O2	0.0281 (10)	0.0237 (9)	0.0130 (7)	−0.0003 (8)	0.0002 (7)	0.0007 (7)
N1	0.0189 (11)	0.0157 (10)	0.0141 (9)	−0.0004 (8)	0.0060 (8)	−0.0035 (7)
C1	0.0160 (11)	0.0183 (12)	0.0115 (10)	0.0010 (9)	0.0068 (8)	−0.0005 (9)
C2	0.0178 (12)	0.0172 (11)	0.0136 (10)	0.0009 (10)	0.0060 (9)	−0.0023 (9)
C3	0.0195 (12)	0.0242 (13)	0.0139 (10)	0.0012 (10)	0.0053 (9)	−0.0015 (9)
C4	0.0187 (13)	0.0274 (14)	0.0197 (11)	−0.0005 (11)	0.0014 (9)	−0.0060 (10)
C5	0.0190 (13)	0.0225 (13)	0.0212 (12)	−0.0035 (10)	0.0055 (9)	−0.0054 (10)
C6	0.0200 (12)	0.0194 (12)	0.0162 (11)	−0.0006 (10)	0.0082 (9)	−0.0038 (9)
C7	0.0267 (14)	0.0195 (12)	0.0206 (12)	−0.0056 (11)	0.0094 (10)	−0.0012 (10)
C8	0.0282 (14)	0.0228 (13)	0.0142 (11)	−0.0025 (11)	0.0090 (10)	0.0026 (10)
C9	0.0237 (13)	0.0241 (13)	0.0118 (10)	−0.0001 (11)	0.0053 (9)	0.0001 (9)
C10	0.0163 (11)	0.0175 (11)	0.0125 (10)	0.0012 (9)	0.0067 (8)	−0.0023 (9)
C11	0.0179 (12)	0.0194 (12)	0.0121 (10)	0.0021 (10)	0.0051 (8)	−0.0023 (9)
C12	0.0172 (12)	0.0157 (11)	0.0111 (9)	−0.0002 (9)	0.0025 (8)	0.0008 (8)
C13	0.0182 (12)	0.0157 (11)	0.0118 (10)	0.0012 (9)	0.0033 (8)	0.0004 (8)
C14	0.0211 (12)	0.0165 (11)	0.0116 (10)	0.0007 (10)	0.0053 (8)	0.0005 (9)
C15	0.0162 (12)	0.0215 (12)	0.0142 (10)	0.0018 (10)	0.0051 (9)	−0.0015 (9)
C16	0.0202 (13)	0.0236 (13)	0.0174 (11)	0.0003 (10)	0.0067 (9)	−0.0021 (10)
C17	0.0272 (14)	0.0216 (13)	0.0228 (12)	−0.0023 (11)	0.0105 (10)	−0.0073 (10)
C18	0.0336 (16)	0.0173 (13)	0.0298 (13)	0.0024 (11)	0.0093 (11)	0.0036 (10)
C19	0.0263 (14)	0.0213 (13)	0.0200 (11)	0.0032 (11)	0.0072 (10)	0.0036 (10)
C20	0.0176 (12)	0.0171 (11)	0.0154 (10)	0.0010 (10)	0.0050 (9)	0.0012 (9)
C21	0.0158 (11)	0.0188 (12)	0.0137 (10)	0.0001 (10)	0.0045 (8)	0.0027 (9)
C22	0.0179 (12)	0.0166 (11)	0.0155 (10)	−0.0015 (9)	0.0035 (9)	0.0004 (9)
C23	0.0229 (13)	0.0168 (12)	0.0156 (10)	−0.0028 (10)	0.0056 (9)	−0.0019 (9)
C24	0.0216 (13)	0.0134 (11)	0.0162 (10)	−0.0021 (10)	0.0076 (9)	−0.0008 (9)
C25	0.0204 (13)	0.0196 (12)	0.0198 (11)	0.0015 (10)	0.0056 (9)	0.0000 (9)
C26	0.0182 (13)	0.0227 (13)	0.0280 (13)	0.0002 (11)	0.0082 (10)	0.0002 (10)
C27	0.0257 (13)	0.0157 (11)	0.0170 (11)	−0.0013 (10)	0.0129 (9)	−0.0027 (9)
C28	0.0259 (14)	0.0183 (12)	0.0163 (11)	−0.0009 (10)	0.0058 (9)	0.0012 (9)
C29	0.0192 (13)	0.0205 (12)	0.0203 (11)	−0.0008 (10)	0.0049 (9)	0.0001 (10)
C30	0.0231 (13)	0.0237 (13)	0.0217 (12)	0.0012 (11)	0.0069 (10)	−0.0045 (10)
C31	0.0250 (14)	0.0202 (13)	0.0225 (12)	−0.0011 (11)	0.0144 (10)	−0.0019 (10)

F1—C31	1.343 (3)	C14—H14A	0.9900
F2—C31	1.339 (3)	C14—H14B	0.9900
F3—C31	1.332 (3)	C15—C16	1.390 (3)
O1—C1	1.215 (3)	C15—C20	1.395 (3)
O2—C21	1.216 (3)	C16—C17	1.392 (4)
N1—C30	1.457 (3)	C16—H16A	0.9500
N1—C23	1.462 (3)	C17—C18	1.397 (4)
N1—C12	1.465 (3)	C17—H17A	0.9500
C1—C2	1.470 (3)	C18—C19	1.385 (4)
C1—C12	1.586 (3)	C18—H18A	0.9500
C2—C3	1.383 (3)	C19—C20	1.390 (3)
C2—C11	1.408 (3)	C19—H19A	0.9500
C3—C4	1.410 (4)	C20—C21	1.476 (3)
C3—H3A	0.9500	C22—C24	1.517 (3)
C4—C5	1.384 (4)	C22—C23	1.538 (4)
C4—H4A	0.9500	C22—H22A	1.0000
C5—C6	1.417 (3)	C23—H23A	0.9900
C5—H5A	0.9500	C23—H23B	0.9900
C6—C11	1.402 (3)	C24—C25	1.385 (4)
C6—C7	1.423 (3)	C24—C29	1.404 (3)
C7—C8	1.374 (3)	C25—C26	1.395 (4)
C7—H7A	0.9500	C25—H25A	0.9500
C8—C9	1.419 (4)	C26—C27	1.389 (3)
C8—H8A	0.9500	C26—H26A	0.9500
C9—C10	1.370 (3)	C27—C28	1.387 (4)
C9—H9A	0.9500	C27—C31	1.495 (4)
C10—C11	1.417 (3)	C28—C29	1.390 (4)
C10—C12	1.526 (3)	C28—H28A	0.9500
C12—C13	1.573 (4)	C29—H29A	0.9500
C13—C21	1.553 (3)	C30—H30A	0.9800
C13—C14	1.555 (3)	C30—H30B	0.9800
C13—C22	1.565 (3)	C30—H30C	0.9800
C14—C15	1.506 (3)
C30—N1—C23	114.8 (2)	C17—C16—H16A	120.8
C30—N1—C12	115.90 (19)	C16—C17—C18	121.5 (2)
C23—N1—C12	106.87 (18)	C16—C17—H17A	119.3
O1—C1—C2	127.3 (2)	C18—C17—H17A	119.3
O1—C1—C12	124.5 (2)	C19—C18—C17	120.3 (2)
C2—C1—C12	108.11 (19)	C19—C18—H18A	119.9
C3—C2—C11	120.0 (2)	C17—C18—H18A	119.9
C3—C2—C1	132.3 (2)	C18—C19—C20	118.1 (2)
C11—C2—C1	107.72 (19)	C18—C19—H19A	121.0
C2—C3—C4	118.0 (2)	C20—C19—H19A	121.0
C2—C3—H3A	121.0	C19—C20—C15	122.1 (2)
C4—C3—H3A	121.0	C19—C20—C21	128.9 (2)
C5—C4—C3	121.9 (2)	C15—C20—C21	109.0 (2)
C5—C4—H4A	119.1	O2—C21—C20	127.1 (2)
C3—C4—H4A	119.1	O2—C21—C13	125.6 (2)
C4—C5—C6	121.2 (2)	C20—C21—C13	107.31 (18)
C4—C5—H5A	119.4	C24—C22—C23	114.6 (2)
C6—C5—H5A	119.4	C24—C22—C13	116.69 (19)
C11—C6—C5	115.9 (2)	C23—C22—C13	104.93 (19)
C11—C6—C7	116.4 (2)	C24—C22—H22A	106.7
C5—C6—C7	127.6 (2)	C23—C22—H22A	106.7
C8—C7—C6	119.9 (2)	C13—C22—H22A	106.7
C8—C7—H7A	120.1	N1—C23—C22	103.67 (19)
C6—C7—H7A	120.1	N1—C23—H23A	111.0
C7—C8—C9	122.4 (2)	C22—C23—H23A	111.0
C7—C8—H8A	118.8	N1—C23—H23B	111.0
C9—C8—H8A	118.8	C22—C23—H23B	111.0
C10—C9—C8	119.3 (2)	H23A—C23—H23B	109.0
C10—C9—H9A	120.3	C25—C24—C29	118.6 (2)
C8—C9—H9A	120.4	C25—C24—C22	119.6 (2)
C9—C10—C11	118.1 (2)	C29—C24—C22	121.7 (2)
C9—C10—C12	132.7 (2)	C24—C25—C26	121.4 (2)
C11—C10—C12	109.21 (19)	C24—C25—H25A	119.3
C6—C11—C2	123.0 (2)	C26—C25—H25A	119.3
C6—C11—C10	123.9 (2)	C27—C26—C25	119.4 (2)
C2—C11—C10	113.0 (2)	C27—C26—H26A	120.3
N1—C12—C10	112.60 (19)	C25—C26—H26A	120.3
N1—C12—C13	101.81 (18)	C28—C27—C26	120.0 (2)
C10—C12—C13	117.51 (19)	C28—C27—C31	120.0 (2)
N1—C12—C1	113.36 (18)	C26—C27—C31	119.9 (2)
C10—C12—C1	101.53 (17)	C27—C28—C29	120.3 (2)
C13—C12—C1	110.51 (18)	C27—C28—H28A	119.8
C21—C13—C14	102.34 (18)	C29—C28—H28A	119.8
C21—C13—C22	110.03 (17)	C28—C29—C24	120.2 (2)
C14—C13—C22	119.3 (2)	C28—C29—H29A	119.9
C21—C13—C12	107.02 (19)	C24—C29—H29A	119.9
C14—C13—C12	113.39 (18)	N1—C30—H30A	109.5
C22—C13—C12	104.30 (19)	N1—C30—H30B	109.5
C15—C14—C13	104.15 (18)	H30A—C30—H30B	109.5
C15—C14—H14A	110.9	N1—C30—H30C	109.5
C13—C14—H14A	110.9	H30A—C30—H30C	109.5
C15—C14—H14B	110.9	H30B—C30—H30C	109.5
C13—C14—H14B	110.9	F3—C31—F2	106.7 (2)
H14A—C14—H14B	108.9	F3—C31—F1	105.7 (2)
C16—C15—C20	119.7 (2)	F2—C31—F1	105.8 (2)
C16—C15—C14	129.1 (2)	F3—C31—C27	113.2 (2)
C20—C15—C14	111.2 (2)	F2—C31—C27	112.7 (2)
C15—C16—C17	118.4 (2)	F1—C31—C27	112.2 (2)
C15—C16—H16A	120.8
O1—C1—C2—C3	−5.3 (5)	C22—C13—C14—C15	−145.3 (2)
C12—C1—C2—C3	178.6 (3)	C12—C13—C14—C15	91.2 (2)
O1—C1—C2—C11	171.9 (2)	C13—C14—C15—C16	−163.4 (3)
C12—C1—C2—C11	−4.2 (3)	C13—C14—C15—C20	18.0 (3)
C11—C2—C3—C4	0.4 (4)	C20—C15—C16—C17	−0.4 (4)
C1—C2—C3—C4	177.3 (3)	C14—C15—C16—C17	−178.8 (3)
C2—C3—C4—C5	−1.4 (4)	C15—C16—C17—C18	1.2 (4)
C3—C4—C5—C6	0.5 (4)	C16—C17—C18—C19	−0.6 (4)
C4—C5—C6—C11	1.4 (4)	C17—C18—C19—C20	−0.8 (4)
C4—C5—C6—C7	−176.6 (3)	C18—C19—C20—C15	1.7 (4)
C11—C6—C7—C8	−1.2 (4)	C18—C19—C20—C21	−176.6 (3)
C5—C6—C7—C8	176.8 (3)	C16—C15—C20—C19	−1.1 (4)
C6—C7—C8—C9	0.9 (4)	C14—C15—C20—C19	177.6 (2)
C7—C8—C9—C10	0.9 (4)	C16—C15—C20—C21	177.5 (2)
C8—C9—C10—C11	−2.2 (4)	C14—C15—C20—C21	−3.8 (3)
C8—C9—C10—C12	−179.9 (3)	C19—C20—C21—O2	−13.3 (4)
C5—C6—C11—C2	−2.5 (4)	C15—C20—C21—O2	168.3 (3)
C7—C6—C11—C2	175.8 (2)	C19—C20—C21—C13	166.2 (3)
C5—C6—C11—C10	−178.5 (2)	C15—C20—C21—C13	−12.3 (3)
C7—C6—C11—C10	−0.2 (4)	C14—C13—C21—O2	−158.2 (2)
C3—C2—C11—C6	1.6 (4)	C22—C13—C21—O2	−30.4 (3)
C1—C2—C11—C6	−176.0 (2)	C12—C13—C21—O2	82.3 (3)
C3—C2—C11—C10	178.0 (2)	C14—C13—C21—C20	22.3 (2)
C1—C2—C11—C10	0.4 (3)	C22—C13—C21—C20	150.1 (2)
C9—C10—C11—C6	1.9 (4)	C12—C13—C21—C20	−97.1 (2)
C12—C10—C11—C6	−179.9 (2)	C21—C13—C22—C24	−120.0 (2)
C9—C10—C11—C2	−174.4 (2)	C14—C13—C22—C24	−2.2 (3)
C12—C10—C11—C2	3.8 (3)	C12—C13—C22—C24	125.5 (2)
C30—N1—C12—C10	61.1 (3)	C21—C13—C22—C23	112.0 (2)
C23—N1—C12—C10	−169.48 (19)	C14—C13—C22—C23	−130.3 (2)
C30—N1—C12—C13	−172.15 (19)	C12—C13—C22—C23	−2.5 (2)
C23—N1—C12—C13	−42.7 (2)	C30—N1—C23—C22	171.83 (18)
C30—N1—C12—C1	−53.5 (3)	C12—N1—C23—C22	41.8 (2)
C23—N1—C12—C1	76.0 (2)	C24—C22—C23—N1	−151.82 (18)
C9—C10—C12—N1	50.4 (4)	C13—C22—C23—N1	−22.5 (2)
C11—C10—C12—N1	−127.4 (2)	C23—C22—C24—C25	−128.6 (2)
C9—C10—C12—C13	−67.4 (3)	C13—C22—C24—C25	108.2 (2)
C11—C10—C12—C13	114.8 (2)	C23—C22—C24—C29	50.6 (3)
C9—C10—C12—C1	172.0 (3)	C13—C22—C24—C29	−72.5 (3)
C11—C10—C12—C1	−5.8 (2)	C29—C24—C25—C26	−1.7 (4)
O1—C1—C12—N1	−49.2 (3)	C22—C24—C25—C26	177.6 (2)
C2—C1—C12—N1	127.1 (2)	C24—C25—C26—C27	0.9 (4)
O1—C1—C12—C10	−170.2 (2)	C25—C26—C27—C28	0.6 (4)
C2—C1—C12—C10	6.0 (2)	C25—C26—C27—C31	−176.3 (2)
O1—C1—C12—C13	64.4 (3)	C26—C27—C28—C29	−1.5 (4)
C2—C1—C12—C13	−119.4 (2)	C31—C27—C28—C29	175.4 (2)
N1—C12—C13—C21	−90.2 (2)	C27—C28—C29—C24	0.7 (4)
C10—C12—C13—C21	33.3 (2)	C25—C24—C29—C28	0.8 (4)
C1—C12—C13—C21	149.07 (18)	C22—C24—C29—C28	−178.4 (2)
N1—C12—C13—C14	157.69 (18)	C28—C27—C31—F3	160.1 (2)
C10—C12—C13—C14	−78.8 (2)	C26—C27—C31—F3	−23.0 (3)
C1—C12—C13—C14	37.0 (3)	C28—C27—C31—F2	38.9 (3)
N1—C12—C13—C22	26.4 (2)	C26—C27—C31—F2	−144.2 (2)
C10—C12—C13—C22	149.85 (18)	C28—C27—C31—F1	−80.4 (3)
C1—C12—C13—C22	−94.3 (2)	C26—C27—C31—F1	96.5 (3)
C21—C13—C14—C15	−23.7 (2)

D—H···A	D—H	H···A	D···A	D—H···A
C29—H29A···O1	0.95	2.29	3.166 (3)	153
C4—H4A···O2i	0.95	2.52	3.364 (3)	147
C16—H16A···N1ii	0.95	2.51	3.429 (3)	163
C26—H26A···O1iii	0.95	2.51	3.324 (3)	144
C5—H5A···Cg1iv	0.95	2.74	3.417 (3)	129

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C15–C20 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C29—H29A⋯O1	0.95	2.29	3.166 (3)	153
C4—H4A⋯O2i	0.95	2.52	3.364 (3)	147
C16—H16A⋯N1ii	0.95	2.51	3.429 (3)	163
C26—H26A⋯O1iii	0.95	2.51	3.324 (3)	144
C5—H5A⋯Cg1iv	0.95	2.74	3.417 (3)	129

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