4'-[5-(4-Fluoro-phen-yl)pyridin-3-yl]-1'-methyl-dispiro-[indan-2,2'-pyrrolidine-3',2''-indan]-1,3,1''-trione.

In the title compound, C(32)H(23)FN(2)O(3), the pyrrolidine ring adopts an envelope conformation. The monoketo- and diketo-substituted five-membered rings are in envelope and half-chair conformations, respectively. The mol-ecular structure is stabilized by an intra-molecular C-H⋯O hydrogen bond, which generates an S(6) ring motif. In the crystal, mol-ecules are linked via inter-molecular C-H⋯N and C-H⋯O hydrogen bonds into a three-dimensional network. The crystal structure is further consolidated by C-H⋯π inter-actions.

Related literature

For general background to and the biological activity of the title compound, see: Chande et al. (2005 ▶); Prasanna et al. (2010 ▶); Karthikeyan et al. (2010 ▶); Dye (2002 ▶); Duncan & Barry (2004 ▶). For related structures, see: Kumar et al. (2010 ▶); Wei et al. (2011 ▶). For reference bond-length data, see: Allen et al. (1987 ▶). 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 ▶). For ring conformations, see: Cremer & Pople (1975 ▶).

Experimental

Crystal data

C32H23FN2O3

M = 502.52

Monoclinic,

a = 14.8997 (2) Å

b = 7.7993 (1) Å

c = 23.0188 (3) Å

β = 112.638 (1)°

V = 2468.86 (6) Å3

Z = 4

Mo Kα radiation

μ = 0.09 mm−1

T = 100 K

0.36 × 0.17 × 0.05 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.968, T max = 0.996

27325 measured reflections

7184 independent reflections

4664 reflections with I > 2σ(I)

R int = 0.057

Refinement

R[F 2 > 2σ(F 2)] = 0.053

wR(F 2) = 0.135

S = 0.99

7184 reflections

344 parameters

H-atom parameters constrained

Δρmax = 0.29 e Å−3

Δρmin = −0.27 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/S1600536811032946/wn2449sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811032946/wn2449Isup2.hkl

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

C32H23FN2O3	F(000) = 1048
Mr = 502.52	Dx = 1.352 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 5035 reflections
a = 14.8997 (2) Å	θ = 2.8–28.1°
b = 7.7993 (1) Å	µ = 0.09 mm−1
c = 23.0188 (3) Å	T = 100 K
β = 112.638 (1)°	Plate, yellow
V = 2468.86 (6) Å3	0.36 × 0.17 × 0.05 mm
Z = 4

Bruker SMART APEXII CCD area-detector diffractometer	7184 independent reflections
Radiation source: fine-focus sealed tube	4664 reflections with I > 2σ(I)
graphite	Rint = 0.057
φ and ω scans	θmax = 30.1°, θmin = 1.9°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −16→20
Tmin = 0.968, Tmax = 0.996	k = −10→10
27325 measured reflections	l = −32→32

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)] = 0.053	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.135	H-atom parameters constrained
S = 0.99	w = 1/[σ2(Fo2) + (0.0641P)2] where P = (Fo2 + 2Fc2)/3
7184 reflections	(Δ/σ)max = 0.001
344 parameters	Δρmax = 0.29 e Å−3
0 restraints	Δρmin = −0.27 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 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 > 2sigma(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	−0.02526 (8)	0.88163 (14)	0.42880 (5)	0.0352 (3)
O1	0.53116 (8)	0.12559 (15)	0.85281 (6)	0.0203 (3)
O2	0.22158 (9)	0.20148 (15)	0.85535 (6)	0.0212 (3)
O3	0.38943 (8)	−0.17977 (14)	0.76020 (6)	0.0187 (3)
N1	0.35687 (10)	0.35355 (16)	0.80293 (6)	0.0142 (3)
N2	0.30185 (11)	0.07049 (18)	0.54724 (7)	0.0200 (3)
C1	0.35388 (12)	0.17247 (19)	0.81705 (7)	0.0133 (3)
C2	0.45362 (12)	0.08860 (19)	0.85599 (8)	0.0146 (3)
C3	0.43827 (12)	−0.03372 (19)	0.90018 (7)	0.0144 (3)
C4	0.50353 (13)	−0.1516 (2)	0.93975 (8)	0.0180 (4)
H4A	0.5677	−0.1626	0.9409	0.022*
C5	0.47110 (14)	−0.2526 (2)	0.97738 (8)	0.0206 (4)
H5A	0.5142	−0.3338	1.0050	0.025*
C6	0.37646 (14)	−0.2379 (2)	0.97576 (8)	0.0232 (4)
H6A	0.3560	−0.3103	1.0015	0.028*
C7	0.31210 (13)	−0.1179 (2)	0.93668 (8)	0.0202 (4)
H7A	0.2481	−0.1062	0.9357	0.024*
C8	0.34458 (12)	−0.0158 (2)	0.89913 (7)	0.0153 (3)
C9	0.29442 (12)	0.1276 (2)	0.85693 (8)	0.0158 (3)
C10	0.30739 (11)	0.09841 (19)	0.74827 (8)	0.0130 (3)
C11	0.31431 (12)	−0.09919 (19)	0.74843 (7)	0.0140 (3)
C12	0.21613 (12)	−0.1679 (2)	0.73393 (8)	0.0155 (3)
C13	0.18807 (12)	−0.3386 (2)	0.73650 (8)	0.0178 (4)
H13A	0.2347	−0.4285	0.7487	0.021*
C14	0.09024 (13)	−0.3714 (2)	0.72068 (9)	0.0224 (4)
H14A	0.0692	−0.4855	0.7225	0.027*
C15	0.02184 (13)	−0.2386 (2)	0.70207 (9)	0.0225 (4)
H15A	−0.0451	−0.2643	0.6909	0.027*
C16	0.05016 (12)	−0.0699 (2)	0.69970 (8)	0.0191 (4)
H16A	0.0033	0.0196	0.6867	0.023*
C17	0.14895 (12)	−0.0346 (2)	0.71677 (7)	0.0150 (3)
C18	0.19694 (11)	0.1362 (2)	0.71821 (8)	0.0155 (3)
H18A	0.1781	0.2198	0.7439	0.019*
H18B	0.1785	0.1826	0.6751	0.019*
C19	0.37211 (12)	0.19184 (19)	0.71845 (8)	0.0137 (3)
H19A	0.4335	0.1243	0.7297	0.016*
C20	0.39874 (12)	0.3643 (2)	0.75442 (8)	0.0156 (3)
H20A	0.4702	0.3790	0.7741	0.019*
H20B	0.3704	0.4618	0.7257	0.019*
C21	0.40153 (13)	0.4657 (2)	0.85715 (8)	0.0187 (4)
H21A	0.3638	0.4615	0.8838	0.028*
H21B	0.4026	0.5836	0.8427	0.028*
H21C	0.4682	0.4275	0.8814	0.028*
C22	0.32635 (12)	0.2035 (2)	0.64733 (8)	0.0150 (3)
C23	0.33944 (12)	0.0714 (2)	0.61049 (8)	0.0171 (3)
H23A	0.3775	−0.0243	0.6315	0.021*
C24	0.24663 (12)	0.2045 (2)	0.51798 (8)	0.0185 (4)
H24A	0.2200	0.2059	0.4733	0.022*
C25	0.22608 (12)	0.3425 (2)	0.54969 (8)	0.0157 (3)
C26	0.26802 (12)	0.3398 (2)	0.61536 (8)	0.0157 (3)
H26A	0.2566	0.4323	0.6385	0.019*
C27	0.16180 (12)	0.4862 (2)	0.51584 (8)	0.0170 (3)
C28	0.08191 (13)	0.4584 (2)	0.45942 (8)	0.0207 (4)
H28A	0.0704	0.3471	0.4412	0.025*
C29	0.01936 (13)	0.5917 (2)	0.42980 (9)	0.0247 (4)
H29A	−0.0349	0.5731	0.3915	0.030*
C30	0.03784 (13)	0.7509 (2)	0.45716 (9)	0.0246 (4)
C31	0.11572 (13)	0.7859 (2)	0.51189 (9)	0.0239 (4)
H31A	0.1265	0.8982	0.5292	0.029*
C32	0.17830 (13)	0.6522 (2)	0.54108 (8)	0.0210 (4)
H32A	0.2332	0.6735	0.5788	0.025*

	U11	U22	U33	U12	U13	U23
F1	0.0311 (7)	0.0361 (6)	0.0309 (7)	0.0124 (5)	0.0036 (5)	0.0117 (5)
O1	0.0139 (6)	0.0242 (6)	0.0226 (7)	0.0003 (5)	0.0068 (5)	0.0041 (5)
O2	0.0162 (6)	0.0261 (6)	0.0231 (7)	0.0044 (5)	0.0097 (5)	0.0004 (5)
O3	0.0148 (6)	0.0168 (6)	0.0249 (7)	0.0031 (5)	0.0082 (5)	0.0019 (5)
N1	0.0177 (7)	0.0118 (6)	0.0132 (7)	−0.0006 (5)	0.0060 (6)	0.0002 (5)
N2	0.0198 (8)	0.0215 (7)	0.0194 (8)	−0.0020 (6)	0.0083 (6)	−0.0038 (6)
C1	0.0131 (8)	0.0136 (7)	0.0130 (8)	0.0008 (6)	0.0049 (6)	0.0015 (6)
C2	0.0146 (8)	0.0132 (7)	0.0151 (8)	0.0009 (6)	0.0047 (6)	−0.0013 (6)
C3	0.0164 (8)	0.0138 (7)	0.0118 (7)	0.0004 (6)	0.0042 (6)	−0.0008 (6)
C4	0.0214 (9)	0.0162 (8)	0.0138 (8)	0.0022 (7)	0.0039 (7)	−0.0014 (6)
C5	0.0305 (10)	0.0135 (8)	0.0141 (8)	0.0027 (7)	0.0044 (7)	0.0019 (6)
C6	0.0372 (11)	0.0181 (8)	0.0165 (9)	−0.0046 (8)	0.0128 (8)	0.0015 (7)
C7	0.0230 (10)	0.0205 (8)	0.0199 (9)	−0.0025 (7)	0.0115 (7)	−0.0004 (7)
C8	0.0176 (8)	0.0154 (7)	0.0126 (8)	−0.0015 (6)	0.0056 (6)	−0.0019 (6)
C9	0.0136 (8)	0.0177 (8)	0.0158 (8)	−0.0008 (6)	0.0051 (7)	−0.0006 (6)
C10	0.0109 (8)	0.0131 (7)	0.0149 (8)	0.0008 (6)	0.0050 (6)	0.0010 (6)
C11	0.0152 (8)	0.0149 (7)	0.0118 (8)	0.0006 (6)	0.0051 (6)	0.0011 (6)
C12	0.0142 (8)	0.0163 (8)	0.0159 (8)	−0.0016 (6)	0.0059 (7)	−0.0009 (6)
C13	0.0186 (9)	0.0161 (8)	0.0197 (9)	−0.0007 (7)	0.0085 (7)	−0.0006 (7)
C14	0.0238 (10)	0.0186 (8)	0.0266 (10)	−0.0068 (7)	0.0118 (8)	−0.0024 (7)
C15	0.0152 (9)	0.0294 (9)	0.0233 (9)	−0.0054 (7)	0.0078 (7)	−0.0016 (7)
C16	0.0136 (8)	0.0244 (9)	0.0187 (8)	0.0008 (7)	0.0055 (7)	−0.0005 (7)
C17	0.0143 (8)	0.0179 (8)	0.0132 (8)	0.0001 (6)	0.0059 (6)	−0.0003 (6)
C18	0.0135 (8)	0.0157 (8)	0.0163 (8)	0.0019 (6)	0.0047 (6)	0.0024 (6)
C19	0.0122 (8)	0.0150 (7)	0.0147 (8)	−0.0001 (6)	0.0060 (6)	0.0006 (6)
C20	0.0177 (9)	0.0149 (7)	0.0138 (8)	−0.0027 (6)	0.0057 (7)	0.0010 (6)
C21	0.0203 (9)	0.0185 (8)	0.0150 (8)	−0.0016 (7)	0.0043 (7)	−0.0013 (6)
C22	0.0137 (8)	0.0179 (8)	0.0150 (8)	−0.0009 (6)	0.0072 (7)	0.0003 (6)
C23	0.0153 (9)	0.0182 (8)	0.0193 (9)	−0.0005 (7)	0.0082 (7)	−0.0012 (7)
C24	0.0171 (9)	0.0231 (8)	0.0152 (8)	−0.0044 (7)	0.0059 (7)	−0.0027 (7)
C25	0.0135 (8)	0.0183 (8)	0.0162 (8)	−0.0038 (6)	0.0066 (7)	0.0002 (6)
C26	0.0165 (8)	0.0157 (8)	0.0160 (8)	−0.0001 (6)	0.0074 (7)	−0.0013 (6)
C27	0.0150 (8)	0.0220 (8)	0.0149 (8)	−0.0016 (7)	0.0070 (7)	0.0020 (7)
C28	0.0191 (9)	0.0278 (9)	0.0149 (8)	−0.0007 (7)	0.0063 (7)	0.0001 (7)
C29	0.0187 (9)	0.0371 (10)	0.0157 (9)	0.0010 (8)	0.0039 (7)	0.0028 (8)
C30	0.0212 (10)	0.0280 (9)	0.0229 (10)	0.0075 (8)	0.0065 (8)	0.0117 (8)
C31	0.0223 (10)	0.0207 (9)	0.0270 (10)	0.0004 (7)	0.0075 (8)	0.0053 (7)
C32	0.0188 (9)	0.0225 (9)	0.0187 (9)	−0.0021 (7)	0.0038 (7)	0.0037 (7)

F1—C30	1.3702 (19)	C15—C16	1.390 (2)
O1—C2	1.2200 (19)	C15—H15A	0.9500
O2—C9	1.2170 (19)	C16—C17	1.397 (2)
O3—C11	1.2196 (19)	C16—H16A	0.9500
N1—C1	1.4537 (19)	C17—C18	1.506 (2)
N1—C21	1.458 (2)	C18—H18A	0.9900
N1—C20	1.476 (2)	C18—H18B	0.9900
N2—C24	1.341 (2)	C19—C22	1.515 (2)
N2—C23	1.344 (2)	C19—C20	1.549 (2)
C1—C9	1.541 (2)	C19—H19A	1.0000
C1—C2	1.554 (2)	C20—H20A	0.9900
C1—C10	1.574 (2)	C20—H20B	0.9900
C2—C3	1.475 (2)	C21—H21A	0.9800
C3—C4	1.393 (2)	C21—H21B	0.9800
C3—C8	1.394 (2)	C21—H21C	0.9800
C4—C5	1.388 (2)	C22—C26	1.391 (2)
C4—H4A	0.9500	C22—C23	1.395 (2)
C5—C6	1.401 (3)	C23—H23A	0.9500
C5—H5A	0.9500	C24—C25	1.399 (2)
C6—C7	1.393 (2)	C24—H24A	0.9500
C6—H6A	0.9500	C25—C26	1.396 (2)
C7—C8	1.392 (2)	C25—C27	1.485 (2)
C7—H7A	0.9500	C26—H26A	0.9500
C8—C9	1.481 (2)	C27—C28	1.400 (2)
C10—C11	1.545 (2)	C27—C32	1.401 (2)
C10—C18	1.548 (2)	C28—C29	1.388 (2)
C10—C19	1.562 (2)	C28—H28A	0.9500
C11—C12	1.471 (2)	C29—C30	1.371 (3)
C12—C17	1.391 (2)	C29—H29A	0.9500
C12—C13	1.403 (2)	C30—C31	1.372 (3)
C13—C14	1.384 (2)	C31—C32	1.388 (2)
C13—H13A	0.9500	C31—H31A	0.9500
C14—C15	1.399 (2)	C32—H32A	0.9500
C14—H14A	0.9500
C1—N1—C21	115.76 (13)	C12—C17—C18	111.79 (14)
C1—N1—C20	106.41 (12)	C16—C17—C18	128.35 (15)
C21—N1—C20	115.26 (13)	C17—C18—C10	104.82 (12)
C24—N2—C23	117.35 (15)	C17—C18—H18A	110.8
N1—C1—C9	115.33 (13)	C10—C18—H18A	110.8
N1—C1—C2	115.67 (13)	C17—C18—H18B	110.8
C9—C1—C2	101.66 (12)	C10—C18—H18B	110.8
N1—C1—C10	99.85 (12)	H18A—C18—H18B	108.9
C9—C1—C10	112.61 (13)	C22—C19—C20	116.22 (13)
C2—C1—C10	112.26 (12)	C22—C19—C10	113.93 (13)
O1—C2—C3	126.58 (15)	C20—C19—C10	104.16 (13)
O1—C2—C1	125.69 (15)	C22—C19—H19A	107.4
C3—C2—C1	107.60 (13)	C20—C19—H19A	107.4
C4—C3—C8	121.34 (15)	C10—C19—H19A	107.4
C4—C3—C2	128.58 (16)	N1—C20—C19	105.02 (12)
C8—C3—C2	110.06 (14)	N1—C20—H20A	110.7
C5—C4—C3	117.37 (17)	C19—C20—H20A	110.7
C5—C4—H4A	121.3	N1—C20—H20B	110.7
C3—C4—H4A	121.3	C19—C20—H20B	110.7
C4—C5—C6	121.71 (16)	H20A—C20—H20B	108.8
C4—C5—H5A	119.1	N1—C21—H21A	109.5
C6—C5—H5A	119.1	N1—C21—H21B	109.5
C7—C6—C5	120.53 (16)	H21A—C21—H21B	109.5
C7—C6—H6A	119.7	N1—C21—H21C	109.5
C5—C6—H6A	119.7	H21A—C21—H21C	109.5
C8—C7—C6	117.91 (16)	H21B—C21—H21C	109.5
C8—C7—H7A	121.0	C26—C22—C23	116.61 (15)
C6—C7—H7A	121.0	C26—C22—C19	123.18 (14)
C7—C8—C3	121.11 (15)	C23—C22—C19	120.18 (14)
C7—C8—C9	129.14 (16)	N2—C23—C22	124.41 (16)
C3—C8—C9	109.66 (14)	N2—C23—H23A	117.8
O2—C9—C8	126.60 (15)	C22—C23—H23A	117.8
O2—C9—C1	125.80 (15)	N2—C24—C25	123.58 (16)
C8—C9—C1	107.55 (13)	N2—C24—H24A	118.2
C11—C10—C18	104.44 (12)	C25—C24—H24A	118.2
C11—C10—C19	114.49 (13)	C26—C25—C24	117.20 (15)
C18—C10—C19	116.40 (13)	C26—C25—C27	120.58 (15)
C11—C10—C1	111.14 (13)	C24—C25—C27	122.22 (15)
C18—C10—C1	111.13 (13)	C22—C26—C25	120.82 (15)
C19—C10—C1	99.42 (12)	C22—C26—H26A	119.6
O3—C11—C12	127.60 (15)	C25—C26—H26A	119.6
O3—C11—C10	124.71 (15)	C28—C27—C32	118.59 (16)
C12—C11—C10	107.67 (13)	C28—C27—C25	121.06 (15)
C17—C12—C13	121.85 (15)	C32—C27—C25	120.32 (15)
C17—C12—C11	109.63 (14)	C29—C28—C27	120.67 (17)
C13—C12—C11	128.51 (15)	C29—C28—H28A	119.7
C14—C13—C12	117.71 (16)	C27—C28—H28A	119.7
C14—C13—H13A	121.1	C30—C29—C28	118.33 (17)
C12—C13—H13A	121.1	C30—C29—H29A	120.8
C13—C14—C15	120.88 (16)	C28—C29—H29A	120.8
C13—C14—H14A	119.6	F1—C30—C29	118.38 (16)
C15—C14—H14A	119.6	F1—C30—C31	118.15 (17)
C16—C15—C14	121.10 (16)	C29—C30—C31	123.47 (17)
C16—C15—H15A	119.5	C30—C31—C32	117.89 (17)
C14—C15—H15A	119.5	C30—C31—H31A	121.1
C15—C16—C17	118.59 (16)	C32—C31—H31A	121.1
C15—C16—H16A	120.7	C31—C32—C27	121.03 (17)
C17—C16—H16A	120.7	C31—C32—H32A	119.5
C12—C17—C16	119.84 (15)	C27—C32—H32A	119.5
C21—N1—C1—C9	62.03 (19)	C10—C11—C12—C13	−171.27 (16)
C20—N1—C1—C9	−168.47 (13)	C17—C12—C13—C14	0.6 (3)
C21—N1—C1—C2	−56.37 (19)	C11—C12—C13—C14	179.77 (16)
C20—N1—C1—C2	73.13 (16)	C12—C13—C14—C15	0.8 (3)
C21—N1—C1—C10	−177.04 (13)	C13—C14—C15—C16	−0.8 (3)
C20—N1—C1—C10	−47.54 (15)	C14—C15—C16—C17	−0.4 (3)
N1—C1—C2—O1	−34.0 (2)	C13—C12—C17—C16	−1.9 (3)
C9—C1—C2—O1	−159.71 (16)	C11—C12—C17—C16	178.80 (15)
C10—C1—C2—O1	79.72 (19)	C13—C12—C17—C18	179.42 (15)
N1—C1—C2—C3	142.07 (13)	C11—C12—C17—C18	0.13 (19)
C9—C1—C2—C3	16.34 (16)	C15—C16—C17—C12	1.8 (2)
C10—C1—C2—C3	−104.23 (15)	C15—C16—C17—C18	−179.80 (16)
O1—C2—C3—C4	−11.5 (3)	C12—C17—C18—C10	−8.03 (18)
C1—C2—C3—C4	172.51 (15)	C16—C17—C18—C10	173.44 (16)
O1—C2—C3—C8	167.33 (16)	C11—C10—C18—C17	12.09 (16)
C1—C2—C3—C8	−8.67 (18)	C19—C10—C18—C17	139.37 (14)
C8—C3—C4—C5	1.0 (2)	C1—C10—C18—C17	−107.82 (14)
C2—C3—C4—C5	179.71 (16)	C11—C10—C19—C22	82.84 (17)
C3—C4—C5—C6	0.3 (2)	C18—C10—C19—C22	−39.30 (19)
C4—C5—C6—C7	−1.2 (3)	C1—C10—C19—C22	−158.66 (13)
C5—C6—C7—C8	0.8 (3)	C11—C10—C19—C20	−149.54 (13)
C6—C7—C8—C3	0.5 (2)	C18—C10—C19—C20	88.32 (16)
C6—C7—C8—C9	−175.63 (16)	C1—C10—C19—C20	−31.03 (14)
C4—C3—C8—C7	−1.4 (2)	C1—N1—C20—C19	27.63 (16)
C2—C3—C8—C7	179.65 (15)	C21—N1—C20—C19	157.41 (13)
C4—C3—C8—C9	175.39 (14)	C22—C19—C20—N1	130.35 (14)
C2—C3—C8—C9	−3.53 (18)	C10—C19—C20—N1	4.16 (16)
C7—C8—C9—O2	13.4 (3)	C20—C19—C22—C26	−31.0 (2)
C3—C8—C9—O2	−163.05 (16)	C10—C19—C22—C26	90.10 (18)
C7—C8—C9—C1	−169.08 (16)	C20—C19—C22—C23	150.83 (15)
C3—C8—C9—C1	14.43 (18)	C10—C19—C22—C23	−88.05 (18)
N1—C1—C9—O2	33.2 (2)	C24—N2—C23—C22	−1.3 (2)
C2—C1—C9—O2	159.15 (16)	C26—C22—C23—N2	1.8 (2)
C10—C1—C9—O2	−80.52 (19)	C19—C22—C23—N2	−179.93 (15)
N1—C1—C9—C8	−144.31 (14)	C23—N2—C24—C25	−0.5 (2)
C2—C1—C9—C8	−18.35 (16)	N2—C24—C25—C26	1.6 (2)
C10—C1—C9—C8	101.97 (15)	N2—C24—C25—C27	−177.84 (15)
N1—C1—C10—C11	168.49 (13)	C23—C22—C26—C25	−0.5 (2)
C9—C1—C10—C11	−68.64 (16)	C19—C22—C26—C25	−178.74 (15)
C2—C1—C10—C11	45.39 (17)	C24—C25—C26—C22	−1.0 (2)
N1—C1—C10—C18	−75.66 (15)	C27—C25—C26—C22	178.41 (15)
C9—C1—C10—C18	47.21 (17)	C26—C25—C27—C28	−145.25 (17)
C2—C1—C10—C18	161.23 (13)	C24—C25—C27—C28	34.2 (2)
N1—C1—C10—C19	47.52 (14)	C26—C25—C27—C32	32.6 (2)
C9—C1—C10—C19	170.39 (12)	C24—C25—C27—C32	−147.97 (17)
C2—C1—C10—C19	−75.59 (14)	C32—C27—C28—C29	−1.2 (3)
C18—C10—C11—O3	169.18 (15)	C25—C27—C28—C29	176.67 (16)
C19—C10—C11—O3	40.7 (2)	C27—C28—C29—C30	0.0 (3)
C1—C10—C11—O3	−70.9 (2)	C28—C29—C30—F1	−178.37 (16)
C18—C10—C11—C12	−12.43 (17)	C28—C29—C30—C31	0.9 (3)
C19—C10—C11—C12	−140.87 (14)	F1—C30—C31—C32	178.73 (16)
C1—C10—C11—C12	107.48 (15)	C29—C30—C31—C32	−0.6 (3)
O3—C11—C12—C17	−173.71 (16)	C30—C31—C32—C27	−0.7 (3)
C10—C11—C12—C17	7.96 (18)	C28—C27—C32—C31	1.6 (3)
O3—C11—C12—C13	7.1 (3)	C25—C27—C32—C31	−176.31 (16)

Cg1 is the centroid of the N2/C22–C26 pyridyl ring.

D—H···A	D—H	H···A	D···A	D—H···A
C6—H6A···N2i	0.95	2.56	3.476 (2)	163
C13—H13A···N1ii	0.95	2.45	3.387 (2)	168
C15—H15A···O2iii	0.95	2.44	3.381 (3)	169
C18—H18A···O2	0.99	2.40	3.077 (2)	125
C20—H20A···O3iv	0.99	2.55	3.318 (2)	135
C4—H4A···Cg1v	0.95	2.65	3.552 (2)	159

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the N2/C22–C26 pyridyl ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C6—H6A⋯N2i	0.95	2.56	3.476 (2)	163
C13—H13A⋯N1ii	0.95	2.45	3.387 (2)	168
C15—H15A⋯O2iii	0.95	2.44	3.381 (3)	169
C18—H18A⋯O2	0.99	2.40	3.077 (2)	125
C20—H20A⋯O3iv	0.99	2.55	3.318 (2)	135
C4—H4A⋯Cg1v	0.95	2.65	3.552 (2)	159

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