4,8,9,10-Tetra­kis(4-fluoro­phen­yl)-1,3-diaza­tricyclo­[3.3.1.1]decan-6-one

Natarajan, S.; Priya, V.S.; Vijayakumar, V.; Suresh, J.; Lakshman, P.L.N.

doi:10.1107/S160053680902090X

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 65| Part 7| July 2009| Page o1530

doi:10.1107/S160053680902090X

Open

access

4,8,9,10-Tetrakis(4-fluorophenyl)-1,3-diazatricyclo[3.3.1.1]decan-6-one

S. Natarajan,^a V. Sudha Priya,^b V. Vijayakumar,^b J. Suresh ^c and P. L. Nilantha Lakshman ^d ^*

^aDepartment of Physics, Madurai Kamaraj University, Madurai 625 021, India, ^bOrganic Chemistry Division, School of Science and Humanities, VIT University, Vellore 632 014, India, ^cDepartment of Physics, The Madura College, Madurai 625 011, India, and ^dDepartment of Food Science and Technology, Faculty of Agriculture, University of Ruhuna, Mapalana, Kamburupitiya 81100, Sri Lanka
^*Correspondence e-mail: nilanthalakshman@yahoo.co.uk

(Received 21 May 2009; accepted 2 June 2009; online 10 June 2009)

In the title compound, C₃₂H₂₄F₄N₂O, all four six-membered rings that constitute the diazaadamantanone cage adopt chair conformations. Two of the four fluorophenyl substituents occupy axial positions and the other two occupy equatorial positions relative to their respective C₅N rings of the adamantane framework. The crystal structure is stabilized by C—H⋯O interactions, generating a C(5) chain along the a axis.

Related literature

For the biological properties of 1,3-diazaadamantane compounds, see: Fernandez et al. (1990 ). For related structures, see: Krishnakumar et al. (2001 ); Subha Nandhini et al. (2002 ). For graph-set notation of hydrogen-bond motifs, see: Etter et al. (1990 ).

Experimental

Crystal data

C₃₂H₂₄F₄N₂O
M_r = 528.53
Monoclinic, P 2₁ /c
a = 6.8432 (7) Å
b = 12.5045 (11) Å
c = 28.8930 (15) Å
β = 92.393 (12)°
V = 2470.2 (4) Å³
Z = 4
Mo Kα radiation
μ = 0.11 mm⁻¹
T = 293 K
0.18 × 0.14 × 0.11 mm

Data collection

Nonius MACH-3 diffractometer
Absorption correction: ψ scan (North et al., 1968 ) T_min = 0.981, T_max = 0.988
5226 measured reflections
4311 independent reflections
2643 reflections with I > 2σ(I)
R_int = 0.030
2 standard reflections frequency: 60 min intensity decay: none

Refinement

R[F² > 2σ(F²)] = 0.038
wR(F²) = 0.105
S = 1.02
4311 reflections
352 parameters
H-atom parameters constrained
Δρ_max = 0.15 e Å⁻³
Δρ_min = −0.19 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C30—H30⋯O1ⁱ	0.98	2.56	3.415 (2)	146
Symmetry code: (i) x-1, y, z.

Data collection: CAD-4 EXPRESS (Enraf–Nonius, 1994 ); cell refinement: CAD-4 EXPRESS; data reduction: XCAD4 (Harms & Wocadlo, 1996 ); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009 ); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S160053680902090X/ci2811sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S160053680902090X/ci2811Isup2.hkl

checkCIF report

Comment top

1,3-Diazaadamantane systems are of pharmacological significance and are potentially interesting as anticholinergic compounds (Fernandez et al., 1990).

In the title molecule (Fig. 1), no significant differences in the geometry of the diazaadamantanone cage are seen, since it is known to be inherently rigid and symmetrical. All the four six-membered rings which constitute the diaza-adamantanone cage, adopt chair conformations; this is the most preferred conformation for adamantanones, irrespective of substitutions, as in related structures previously studied (Krishnakumar et al., 2001; Subha Nandhini et al., 2002). In this structure, two of the four phenyl substituents occupy axial and the other two occupy equatorial positions relative to their respective C₅N rings of the adamantane framework as shown by the torsion angles C19—C28—C29—C32, C32—C26—C27—C1, C7—C25—C26—C32 and C13—C30—C29—C32 of -170.43 (17)°, 173.74 (17)°, -71.5 (2) and 77.5 (2)°, respectively.

Intermolecular C—H···O interactions form linear chains running along the a-axis generating a graph set motif C(5) (Etter et al., 1990) (Table 1 and Fig. 2). These chains do not link through any marked C—H···O interactions.

Related literature top

For biological properties of 1,3-diazaadamantane compounds, see: Fernandez et al. (1990). For related structures, see: Krishnakumar et al. (2001); Subha Nandhini et al. (2002). For graph-set notation of hydrogen-bond motifs, see: Etter et al. (1990).

Experimental top

2,4,6,8-Tetrakis(4-fluorophenyl)-3,7-diazabicyclo[3.3.1]nonan-9-one (2.5 g) was dissolved in C₆H₆ and 5 ml of aq. formalin was added. The mixture was shaken vigorously for 15 min. The C₆H₆ layer was separated and evaporated to get the crude 1,3-diazaadamantanone and recrystallized using ethanol-benzene (4:1) mixture. The purity of the compound was checked by TLC and the melting point was recorded (yield 78%, m.p. 529 K).

Computing details top

Data collection: CAD-4 EXPRESS (Enraf–Nonius, 1994); cell refinement: CAD-4 EXPRESS (Enraf–Nonius, 1994); data reduction: XCAD4 (Harms & Wocadlo, 1996); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structure of the title compound, showing 30% probability displacement ellipsoids and the atom-numbering scheme.
	Fig. 2. Partial packing view down the b-axis. Atoms that do not take part in the H-bond are omitted for clarity.

4,8,9,10-Tetrakis(4-fluorophenyl)-1,3-diazatricyclo[3.3.1.1]decan-6-one top

Crystal data top

C₃₂H₂₄F₄N₂O	F(000) = 1096
M_r = 528.53	D_x = 1.421 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 25 reflections
a = 6.8432 (7) Å	θ = 2–25°
b = 12.5045 (11) Å	µ = 0.11 mm⁻¹
c = 28.8930 (15) Å	T = 293 K
β = 92.393 (12)°	Block, colourless
V = 2470.2 (4) Å³	0.18 × 0.14 × 0.11 mm
Z = 4

Data collection top

Nonius MACH-3 diffractometer	2643 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.030
Graphite monochromator	θ_max = 24.9°, θ_min = 2.2°
ω–2θ scans	h = 0→8
Absorption correction: ψ scan (North et al., 1968)	k = −1→14
T_min = 0.981, T_max = 0.988	l = −34→34
5226 measured reflections	2 standard reflections every 60 min
4311 independent reflections	intensity decay: none

Refinement top

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)] = 0.038	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.105	H-atom parameters constrained
S = 1.02	w = 1/[σ²(F_o²) + (0.0383P)² + 0.9132P] where P = (F_o² + 2F_c²)/3
4311 reflections	(Δ/σ)_max < 0.001
352 parameters	Δρ_max = 0.15 e Å⁻³
0 restraints	Δρ_min = −0.19 e Å⁻³

Crystal data top

C₃₂H₂₄F₄N₂O	V = 2470.2 (4) Å³
M_r = 528.53	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 6.8432 (7) Å	µ = 0.11 mm⁻¹
b = 12.5045 (11) Å	T = 293 K
c = 28.8930 (15) Å	0.18 × 0.14 × 0.11 mm
β = 92.393 (12)°

Data collection top

Nonius MACH-3 diffractometer	2643 reflections with I > 2σ(I)
Absorption correction: ψ scan (North et al., 1968)	R_int = 0.030
T_min = 0.981, T_max = 0.988	2 standard reflections every 60 min
5226 measured reflections	intensity decay: none
4311 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.038	0 restraints
wR(F²) = 0.105	H-atom parameters constrained
S = 1.02	Δρ_max = 0.15 e Å⁻³
4311 reflections	Δρ_min = −0.19 e Å⁻³
352 parameters

Special details top

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 (Å²) top

	x	y	z	U_iso*/U_eq
F1	0.4689 (2)	0.36204 (14)	0.13950 (4)	0.0733 (5)
N2	0.1830 (2)	0.24192 (14)	0.41569 (6)	0.0358 (4)
O1	0.6262 (2)	0.13710 (13)	0.34356 (5)	0.0509 (4)
N1	0.0911 (2)	0.27089 (13)	0.33278 (5)	0.0338 (4)
C31	0.0364 (3)	0.28261 (18)	0.38120 (7)	0.0356 (5)
H31A	−0.0859	0.2451	0.3852	0.043*
H31B	0.0138	0.3578	0.3873	0.043*
C13	0.1194 (3)	0.12606 (16)	0.27355 (7)	0.0354 (5)
C25	0.2719 (3)	0.33390 (17)	0.32685 (7)	0.0364 (5)
H25	0.2421	0.4070	0.3366	0.044*
C19	0.0608 (3)	0.05446 (18)	0.42272 (7)	0.0383 (5)
C7	0.3307 (3)	0.34202 (17)	0.27660 (7)	0.0368 (5)
F2	0.1029 (3)	0.06663 (15)	0.13313 (5)	0.0867 (5)
C26	0.4369 (3)	0.29316 (18)	0.36103 (7)	0.0370 (5)
H26	0.5580	0.3336	0.3573	0.044*
C30	0.1145 (3)	0.15392 (16)	0.32469 (7)	0.0341 (5)
H30	−0.0045	0.1206	0.3357	0.041*
C28	0.2248 (3)	0.12796 (17)	0.40808 (7)	0.0370 (5)
H28	0.3401	0.1104	0.4279	0.044*
C16	0.1080 (4)	0.0848 (2)	0.17976 (8)	0.0538 (6)
F3	0.3014 (3)	0.71627 (13)	0.48734 (7)	0.0909 (6)
C27	0.3665 (3)	0.30274 (18)	0.41170 (7)	0.0382 (5)
H27	0.4653	0.2671	0.4318	0.046*
F4	−0.3548 (3)	−0.15156 (15)	0.47007 (6)	0.0952 (6)
C29	0.2842 (3)	0.11061 (17)	0.35659 (7)	0.0352 (5)
H29	0.3084	0.0348	0.3504	0.042*
C32	0.4680 (3)	0.17575 (18)	0.35196 (7)	0.0370 (5)
C1	0.3471 (3)	0.41640 (19)	0.42984 (7)	0.0418 (5)
C14	0.2848 (3)	0.09058 (18)	0.25191 (7)	0.0443 (6)
H14	0.4006	0.0799	0.2693	0.053*
C2	0.4283 (4)	0.5051 (2)	0.40927 (8)	0.0587 (7)
H2	0.4948	0.4964	0.3821	0.070*
C9	0.5671 (4)	0.3332 (2)	0.21705 (8)	0.0495 (6)
H9	0.6946	0.3219	0.2082	0.059*
C12	0.1894 (3)	0.37033 (18)	0.24280 (7)	0.0450 (6)
H12	0.0622	0.3841	0.2513	0.054*
C10	0.4229 (4)	0.35754 (19)	0.18512 (7)	0.0495 (6)
C11	0.2350 (4)	0.3783 (2)	0.19679 (8)	0.0526 (6)
H11	0.1402	0.3973	0.1743	0.063*
C8	0.5205 (3)	0.32557 (18)	0.26322 (7)	0.0439 (6)
H8	0.6180	0.3092	0.2855	0.053*
C18	−0.0533 (3)	0.13593 (18)	0.24691 (7)	0.0434 (5)
H18	−0.1670	0.1561	0.2611	0.052*
C24	0.0710 (4)	−0.0547 (2)	0.41421 (8)	0.0505 (6)
H24	0.1739	−0.0815	0.3977	0.061*
C20	−0.0907 (3)	0.0918 (2)	0.44877 (7)	0.0464 (6)
H20	−0.0974	0.1642	0.4558	0.056*
C17	−0.0600 (4)	0.1166 (2)	0.19989 (8)	0.0514 (6)
H17	−0.1759	0.1249	0.1823	0.062*
C6	0.2532 (3)	0.4316 (2)	0.47098 (8)	0.0523 (6)
H6	0.1993	0.3732	0.4858	0.063*
C23	−0.0689 (4)	−0.1245 (2)	0.42991 (9)	0.0625 (7)
H23	−0.0620	−0.1975	0.4239	0.075*
C15	0.2792 (4)	0.0710 (2)	0.20472 (8)	0.0546 (7)
H15	0.3910	0.0487	0.1902	0.066*
C4	0.3170 (4)	0.6172 (2)	0.46791 (10)	0.0617 (7)
C21	−0.2320 (4)	0.0232 (2)	0.46442 (8)	0.0560 (7)
H21	−0.3347	0.0488	0.4814	0.067*
C22	−0.2172 (4)	−0.0828 (3)	0.45442 (8)	0.0616 (8)
C5	0.2387 (4)	0.5326 (2)	0.49038 (10)	0.0615 (8)
H5	0.1768	0.5423	0.5181	0.074*
C3	0.4128 (4)	0.6063 (2)	0.42818 (10)	0.0685 (8)
H3	0.4669	0.6654	0.4139	0.082*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
F1	0.0896 (11)	0.0928 (12)	0.0383 (8)	−0.0097 (10)	0.0128 (7)	0.0036 (8)
N2	0.0323 (9)	0.0394 (11)	0.0357 (9)	−0.0019 (8)	0.0017 (7)	−0.0023 (8)
O1	0.0307 (8)	0.0599 (11)	0.0623 (10)	0.0042 (8)	0.0051 (7)	−0.0008 (9)
N1	0.0316 (9)	0.0363 (10)	0.0337 (9)	0.0000 (8)	0.0032 (7)	−0.0020 (8)
C31	0.0314 (11)	0.0382 (13)	0.0375 (11)	0.0032 (10)	0.0040 (9)	−0.0049 (10)
C13	0.0386 (11)	0.0286 (11)	0.0392 (12)	−0.0036 (10)	0.0028 (9)	−0.0024 (9)
C25	0.0376 (12)	0.0350 (12)	0.0364 (11)	−0.0012 (10)	0.0013 (9)	−0.0015 (9)
C19	0.0390 (12)	0.0456 (14)	0.0300 (11)	−0.0034 (10)	−0.0015 (9)	0.0051 (10)
C7	0.0440 (12)	0.0315 (12)	0.0352 (11)	−0.0032 (10)	0.0050 (9)	0.0000 (9)
F2	0.1081 (13)	0.1116 (14)	0.0403 (8)	0.0049 (11)	0.0016 (8)	−0.0214 (9)
C26	0.0317 (11)	0.0431 (13)	0.0363 (12)	−0.0063 (10)	0.0015 (9)	−0.0014 (10)
C30	0.0298 (10)	0.0359 (12)	0.0367 (11)	−0.0018 (9)	0.0032 (8)	−0.0006 (10)
C28	0.0326 (11)	0.0429 (13)	0.0355 (11)	0.0011 (10)	0.0003 (9)	0.0046 (10)
C16	0.0738 (18)	0.0545 (16)	0.0334 (12)	−0.0011 (14)	0.0036 (12)	−0.0111 (12)
F3	0.0874 (12)	0.0606 (11)	0.1247 (15)	−0.0019 (9)	0.0032 (11)	−0.0400 (11)
C27	0.0344 (11)	0.0452 (13)	0.0349 (11)	−0.0040 (10)	0.0002 (9)	−0.0012 (10)
F4	0.0917 (12)	0.1089 (15)	0.0860 (12)	−0.0543 (12)	0.0166 (9)	0.0164 (11)
C29	0.0343 (11)	0.0349 (12)	0.0366 (11)	0.0026 (10)	0.0048 (9)	−0.0002 (9)
C32	0.0311 (11)	0.0489 (14)	0.0310 (11)	0.0014 (10)	0.0014 (8)	0.0037 (10)
C1	0.0380 (12)	0.0483 (14)	0.0388 (12)	−0.0040 (11)	−0.0022 (10)	−0.0056 (11)
C14	0.0439 (13)	0.0451 (14)	0.0443 (13)	0.0032 (11)	0.0053 (10)	−0.0051 (11)
C2	0.0773 (19)	0.0577 (17)	0.0414 (14)	−0.0182 (14)	0.0064 (12)	−0.0071 (13)
C9	0.0503 (14)	0.0525 (15)	0.0464 (14)	−0.0047 (12)	0.0122 (11)	−0.0006 (12)
C12	0.0462 (13)	0.0448 (14)	0.0439 (13)	0.0018 (11)	0.0017 (10)	0.0033 (11)
C10	0.0677 (16)	0.0486 (15)	0.0330 (12)	−0.0102 (13)	0.0104 (11)	0.0017 (11)
C11	0.0605 (16)	0.0575 (16)	0.0393 (13)	−0.0008 (13)	−0.0044 (11)	0.0068 (12)
C8	0.0447 (13)	0.0450 (14)	0.0422 (13)	−0.0032 (11)	0.0036 (10)	0.0033 (11)
C18	0.0403 (12)	0.0467 (14)	0.0433 (13)	−0.0018 (11)	0.0019 (10)	−0.0065 (11)
C24	0.0579 (15)	0.0540 (16)	0.0400 (13)	−0.0074 (13)	0.0064 (11)	0.0006 (12)
C20	0.0456 (13)	0.0530 (15)	0.0409 (12)	−0.0037 (12)	0.0051 (10)	0.0063 (11)
C17	0.0558 (15)	0.0508 (15)	0.0465 (14)	−0.0026 (12)	−0.0120 (11)	−0.0068 (12)
C6	0.0446 (14)	0.0592 (17)	0.0538 (15)	−0.0113 (12)	0.0100 (11)	−0.0125 (13)
C23	0.084 (2)	0.0513 (16)	0.0525 (15)	−0.0258 (15)	0.0025 (14)	0.0015 (13)
C15	0.0599 (16)	0.0589 (17)	0.0458 (14)	0.0066 (13)	0.0135 (12)	−0.0128 (12)
C4	0.0547 (16)	0.0504 (17)	0.0794 (19)	−0.0007 (14)	−0.0064 (14)	−0.0249 (15)
C21	0.0463 (14)	0.076 (2)	0.0463 (14)	−0.0068 (14)	0.0080 (11)	0.0120 (14)
C22	0.0562 (16)	0.083 (2)	0.0458 (15)	−0.0323 (16)	0.0025 (12)	0.0126 (14)
C5	0.0441 (14)	0.073 (2)	0.0679 (18)	−0.0083 (14)	0.0102 (12)	−0.0283 (16)
C3	0.090 (2)	0.0526 (18)	0.0620 (17)	−0.0201 (16)	−0.0039 (15)	−0.0062 (14)

Geometric parameters (Å, º) top

F1—C10	1.369 (2)	C29—C32	1.509 (3)
N2—C28	1.472 (3)	C29—H29	0.98
N2—C31	1.475 (3)	C1—C2	1.386 (3)
N2—C27	1.477 (3)	C1—C6	1.387 (3)
O1—C32	1.219 (2)	C14—C15	1.384 (3)
N1—C31	1.471 (2)	C14—H14	0.93
N1—C25	1.483 (3)	C2—C3	1.384 (4)
N1—C30	1.491 (3)	C2—H2	0.93
C31—H31A	0.97	C9—C10	1.357 (3)
C31—H31B	0.97	C9—C8	1.388 (3)
C13—C18	1.388 (3)	C9—H9	0.93
C13—C14	1.389 (3)	C12—C11	1.381 (3)
C13—C30	1.520 (3)	C12—H12	0.93
C25—C7	1.526 (3)	C10—C11	1.368 (3)
C25—C26	1.555 (3)	C11—H11	0.93
C25—H25	0.98	C8—H8	0.93
C19—C20	1.387 (3)	C18—C17	1.379 (3)
C19—C24	1.390 (3)	C18—H18	0.93
C19—C28	1.524 (3)	C24—C23	1.386 (3)
C7—C8	1.386 (3)	C24—H24	0.93
C7—C12	1.391 (3)	C20—C21	1.383 (3)
F2—C16	1.365 (3)	C20—H20	0.93
C26—C32	1.508 (3)	C17—H17	0.93
C26—C27	1.565 (3)	C6—C5	1.387 (4)
C26—H26	0.98	C6—H6	0.93
C30—C29	1.550 (3)	C23—C22	1.365 (4)
C30—H30	0.98	C23—H23	0.93
C28—C29	1.574 (3)	C15—H15	0.93
C28—H28	0.98	C4—C3	1.352 (4)
C16—C15	1.361 (3)	C4—C5	1.363 (4)
C16—C17	1.369 (3)	C21—C22	1.361 (4)
F3—C4	1.366 (3)	C21—H21	0.93
C27—C1	1.523 (3)	C5—H5	0.93
C27—H27	0.98	C3—H3	0.93
F4—C22	1.366 (3)

C28—N2—C31	111.35 (16)	C26—C32—C29	112.70 (18)
C28—N2—C27	108.43 (16)	C2—C1—C6	117.8 (2)
C31—N2—C27	109.05 (16)	C2—C1—C27	123.86 (19)
C31—N1—C25	107.70 (15)	C6—C1—C27	118.2 (2)
C31—N1—C30	106.28 (16)	C15—C14—C13	120.7 (2)
C25—N1—C30	114.06 (16)	C15—C14—H14	119.7
N1—C31—N2	114.51 (16)	C13—C14—H14	119.7
N1—C31—H31A	108.6	C3—C2—C1	121.6 (2)
N2—C31—H31A	108.6	C3—C2—H2	119.2
N1—C31—H31B	108.6	C1—C2—H2	119.2
N2—C31—H31B	108.6	C10—C9—C8	118.6 (2)
H31A—C31—H31B	107.6	C10—C9—H9	120.7
C18—C13—C14	118.0 (2)	C8—C9—H9	120.7
C18—C13—C30	117.77 (18)	C11—C12—C7	121.0 (2)
C14—C13—C30	124.22 (19)	C11—C12—H12	119.5
N1—C25—C7	113.58 (16)	C7—C12—H12	119.5
N1—C25—C26	109.86 (16)	C9—C10—C11	122.7 (2)
C7—C25—C26	114.37 (17)	C9—C10—F1	118.3 (2)
N1—C25—H25	106.1	C11—C10—F1	119.0 (2)
C7—C25—H25	106.1	C10—C11—C12	118.4 (2)
C26—C25—H25	106.1	C10—C11—H11	120.8
C20—C19—C24	118.1 (2)	C12—C11—H11	120.8
C20—C19—C28	121.6 (2)	C7—C8—C9	120.9 (2)
C24—C19—C28	120.0 (2)	C7—C8—H8	119.5
C8—C7—C12	118.30 (19)	C9—C8—H8	119.5
C8—C7—C25	122.90 (19)	C17—C18—C13	121.6 (2)
C12—C7—C25	118.78 (19)	C17—C18—H18	119.2
C32—C26—C25	108.21 (17)	C13—C18—H18	119.2
C32—C26—C27	106.77 (17)	C23—C24—C19	121.3 (2)
C25—C26—C27	108.98 (17)	C23—C24—H24	119.3
C32—C26—H26	110.9	C19—C24—H24	119.3
C25—C26—H26	110.9	C21—C20—C19	121.2 (2)
C27—C26—H26	110.9	C21—C20—H20	119.4
N1—C30—C13	112.60 (16)	C19—C20—H20	119.4
N1—C30—C29	109.41 (16)	C16—C17—C18	118.4 (2)
C13—C30—C29	116.86 (17)	C16—C17—H17	120.8
N1—C30—H30	105.7	C18—C17—H17	120.8
C13—C30—H30	105.7	C5—C6—C1	120.9 (3)
C29—C30—H30	105.7	C5—C6—H6	119.5
N2—C28—C19	113.13 (17)	C1—C6—H6	119.5
N2—C28—C29	109.52 (16)	C22—C23—C24	117.9 (3)
C19—C28—C29	113.68 (17)	C22—C23—H23	121.0
N2—C28—H28	106.7	C24—C23—H23	121.0
C19—C28—H28	106.7	C16—C15—C14	119.2 (2)
C29—C28—H28	106.7	C16—C15—H15	120.4
C15—C16—F2	119.2 (2)	C14—C15—H15	120.4
C15—C16—C17	122.1 (2)	C3—C4—C5	122.7 (3)
F2—C16—C17	118.7 (2)	C3—C4—F3	119.3 (3)
N2—C27—C1	111.55 (17)	C5—C4—F3	118.0 (3)
N2—C27—C26	109.24 (16)	C22—C21—C20	118.4 (2)
C1—C27—C26	115.36 (18)	C22—C21—H21	120.8
N2—C27—H27	106.7	C20—C21—H21	120.8
C1—C27—H27	106.7	C21—C22—C23	123.1 (2)
C26—C27—H27	106.7	C21—C22—F4	118.9 (3)
C32—C29—C30	111.42 (17)	C23—C22—F4	118.0 (3)
C32—C29—C28	105.00 (16)	C4—C5—C6	118.6 (2)
C30—C29—C28	107.29 (16)	C4—C5—H5	120.7
C32—C29—H29	111.0	C6—C5—H5	120.7
C30—C29—H29	111.0	C4—C3—C2	118.3 (3)
C28—C29—H29	111.0	C4—C3—H3	120.8
O1—C32—C26	123.6 (2)	C2—C3—H3	120.8
O1—C32—C29	123.6 (2)

C25—N1—C31—N2	−61.6 (2)	C25—C26—C32—C29	−57.3 (2)
C30—N1—C31—N2	61.0 (2)	C27—C26—C32—C29	59.9 (2)
C28—N2—C31—N1	−58.1 (2)	C30—C29—C32—O1	−127.1 (2)
C27—N2—C31—N1	61.6 (2)	C28—C29—C32—O1	117.1 (2)
C31—N1—C25—C7	−171.95 (17)	C30—C29—C32—C26	55.6 (2)
C30—N1—C25—C7	70.4 (2)	C28—C29—C32—C26	−60.2 (2)
C31—N1—C25—C26	58.5 (2)	N2—C27—C1—C2	−140.8 (2)
C30—N1—C25—C26	−59.2 (2)	C26—C27—C1—C2	−15.4 (3)
N1—C25—C7—C8	−133.8 (2)	N2—C27—C1—C6	43.4 (3)
C26—C25—C7—C8	−6.6 (3)	C26—C27—C1—C6	168.8 (2)
N1—C25—C7—C12	48.2 (3)	C18—C13—C14—C15	3.2 (3)
C26—C25—C7—C12	175.45 (19)	C30—C13—C14—C15	−177.3 (2)
N1—C25—C26—C32	57.6 (2)	C6—C1—C2—C3	−1.6 (4)
C7—C25—C26—C32	−71.5 (2)	C27—C1—C2—C3	−177.5 (2)
N1—C25—C26—C27	−58.2 (2)	C8—C7—C12—C11	2.2 (3)
C7—C25—C26—C27	172.74 (18)	C25—C7—C12—C11	−179.7 (2)
C31—N1—C30—C13	165.18 (15)	C8—C9—C10—C11	2.2 (4)
C25—N1—C30—C13	−76.3 (2)	C8—C9—C10—F1	−178.2 (2)
C31—N1—C30—C29	−63.10 (19)	C9—C10—C11—C12	−2.4 (4)
C25—N1—C30—C29	55.4 (2)	F1—C10—C11—C12	178.1 (2)
C18—C13—C30—N1	−70.4 (2)	C7—C12—C11—C10	0.1 (4)
C14—C13—C30—N1	110.1 (2)	C12—C7—C8—C9	−2.4 (3)
C18—C13—C30—C29	161.69 (19)	C25—C7—C8—C9	179.6 (2)
C14—C13—C30—C29	−17.8 (3)	C10—C9—C8—C7	0.2 (4)
C31—N2—C28—C19	−74.0 (2)	C14—C13—C18—C17	−3.3 (3)
C27—N2—C28—C19	165.99 (16)	C30—C13—C18—C17	177.3 (2)
C31—N2—C28—C29	53.9 (2)	C20—C19—C24—C23	2.0 (3)
C27—N2—C28—C29	−66.1 (2)	C28—C19—C24—C23	175.5 (2)
C20—C19—C28—N2	−12.0 (3)	C24—C19—C20—C21	−2.4 (3)
C24—C19—C28—N2	174.70 (19)	C28—C19—C20—C21	−175.8 (2)
C20—C19—C28—C29	−137.8 (2)	C15—C16—C17—C18	0.7 (4)
C24—C19—C28—C29	49.0 (3)	F2—C16—C17—C18	−179.3 (2)
C28—N2—C27—C1	−166.90 (17)	C13—C18—C17—C16	1.4 (4)
C31—N2—C27—C1	71.7 (2)	C2—C1—C6—C5	1.0 (4)
C28—N2—C27—C26	64.4 (2)	C27—C1—C6—C5	177.1 (2)
C31—N2—C27—C26	−57.0 (2)	C19—C24—C23—C22	−0.5 (4)
C32—C26—C27—N2	−59.7 (2)	F2—C16—C15—C14	179.3 (2)
C25—C26—C27—N2	57.0 (2)	C17—C16—C15—C14	−0.7 (4)
C32—C26—C27—C1	173.74 (17)	C13—C14—C15—C16	−1.3 (4)
C25—C26—C27—C1	−69.6 (2)	C19—C20—C21—C22	1.3 (4)
N1—C30—C29—C32	−51.9 (2)	C20—C21—C22—C23	0.3 (4)
C13—C30—C29—C32	77.5 (2)	C20—C21—C22—F4	179.4 (2)
N1—C30—C29—C28	62.5 (2)	C24—C23—C22—C21	−0.7 (4)
C13—C30—C29—C28	−168.09 (17)	C24—C23—C22—F4	−179.7 (2)
N2—C28—C29—C32	61.9 (2)	C3—C4—C5—C6	−1.8 (4)
C19—C28—C29—C32	−170.43 (17)	F3—C4—C5—C6	179.9 (2)
N2—C28—C29—C30	−56.7 (2)	C1—C6—C5—C4	0.7 (4)
C19—C28—C29—C30	70.9 (2)	C5—C4—C3—C2	1.2 (4)
C25—C26—C32—O1	125.4 (2)	F3—C4—C3—C2	179.5 (2)
C27—C26—C32—O1	−117.4 (2)	C1—C2—C3—C4	0.6 (4)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C30—H30···O1ⁱ	0.98	2.56	3.415 (2)	146

Symmetry code: (i) x−1, y, z.

Experimental details

Crystal data
Chemical formula	C₃₂H₂₄F₄N₂O
M_r	528.53
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	293
a, b, c (Å)	6.8432 (7), 12.5045 (11), 28.8930 (15)
β (°)	92.393 (12)
V (Å³)	2470.2 (4)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.11
Crystal size (mm)	0.18 × 0.14 × 0.11

Data collection
Diffractometer	Nonius MACH-3 diffractometer
Absorption correction	ψ scan (North et al., 1968)
T_min, T_max	0.981, 0.988
No. of measured, independent and observed [I > 2σ(I)] reflections	5226, 4311, 2643
R_int	0.030
(sin θ/λ)_max (Å⁻¹)	0.593

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.038, 0.105, 1.02
No. of reflections	4311
No. of parameters	352
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.15, −0.19

Computer programs: CAD-4 EXPRESS (Enraf–Nonius, 1994), XCAD4 (Harms & Wocadlo, 1996), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C30—H30···O1ⁱ	0.98	2.56	3.415 (2)	146

Symmetry code: (i) x−1, y, z.

Acknowledgements

The authors thank the DST for the FIST programme.

References

Enraf–Nonius (1994). CAD-4 EXPRESS. Enraf–Nonius, Delft, The Netherlands. Google Scholar
Etter, M. C., MacDonald, J. C. & Bernstein, J. (1990). Acta Cryst. B46, 256–262. CrossRef CAS Web of Science IUCr Journals Google Scholar
Fernandez, M. J., Galvez, E., Lorente, A. & Camunas, J. A. (1990). J. Hetrocycl. Chem. 27, 1355–1359. CrossRef CAS Google Scholar
Harms, K. & Wocadlo, S. (1996). XCAD4. University of Marburg, Germany. Google Scholar
Krishnakumar, R. V., Nandhini, M. S., Vijayakumar, V., Natarajan, S., Sundaravadivelu, M., Perumal, S. & Mostad, A. (2001). Acta Cryst. E57, o860–o862. Web of Science CSD CrossRef IUCr Journals Google Scholar
North, A. C. T., Phillips, D. C. & Mathews, F. S. (1968). Acta Cryst. A24, 351–359. CrossRef IUCr Journals Web of Science Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar
Subha Nandhini, M., Krishnakumar, R. V., Narasimhamurthy, T., Vijayakumar, V., Sundaravadivelu, M. & Natarajan, S. (2002). Acta Cryst. E58, o675–o677. Web of Science CSD CrossRef IUCr Journals Google Scholar