N,N'-[4,4'-Methyl-enebis(4,1-phenyl-ene)]bis-(2,6-difluoro-benzamide).

The complete mol-ecule of the title compound, C(27)H(18)F(4)N(2)O(2), is generated by crystallographic twofold symmetry, with one C atom lying on the rotation axis. The dihedral angle between fluoro-substituted phenyl ring and the adjacent benzene ring is 10.37 (5)°. In the crystal, mol-ecules are connected by N-H⋯O and C-H⋯F hydrogen bonds, resulting in supra-molecular chains propagating along the c direction.

Related literature

For applications of benzamide derivatives, see: Ashwood et al. (1990 ▶); Kees et al. (1989 ▶); Ragavan et al. (2010 ▶); Carmellino et al. (1994 ▶); Rauko et al. (2001 ▶). For a related structure, see: Cronin et al. (2000 ▶). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986 ▶).

Experimental

Crystal data

C27H18F4N2O2

M = 478.43

Monoclinic,

a = 42.0478 (10) Å

b = 5.2980 (1) Å

c = 9.5643 (2) Å

β = 92.522 (2)°

V = 2128.57 (8) Å3

Z = 4

Mo Kα radiation

μ = 0.12 mm−1

T = 100 K

0.48 × 0.38 × 0.05 mm

Data collection

Bruker APEXII DUO CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.946, T max = 0.994

26445 measured reflections

3871 independent reflections

3172 reflections with I > 2σ(I)

R int = 0.031

Refinement

R[F 2 > 2σ(F 2)] = 0.040

wR(F 2) = 0.114

S = 1.06

3871 reflections

163 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.43 e Å−3

Δρmin = −0.21 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/S1600536811024524/hb5924sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811024524/hb5924Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811024524/hb5924Isup3.cml

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

C27H18F4N2O2	F(000) = 984
Mr = 478.43	Dx = 1.493 Mg m−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 8910 reflections
a = 42.0478 (10) Å	θ = 2.9–32.5°
b = 5.2980 (1) Å	µ = 0.12 mm−1
c = 9.5643 (2) Å	T = 100 K
β = 92.522 (2)°	Plate, colourless
V = 2128.57 (8) Å3	0.48 × 0.38 × 0.05 mm
Z = 4

Bruker APEXII DUO CCD diffractometer	3871 independent reflections
Radiation source: fine-focus sealed tube	3172 reflections with I > 2σ(I)
graphite	Rint = 0.031
φ and ω scans	θmax = 32.6°, θmin = 1.9°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −63→63
Tmin = 0.946, Tmax = 0.994	k = −7→7
26445 measured reflections	l = −14→14

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)] = 0.040	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.114	H atoms treated by a mixture of independent and constrained refinement
S = 1.06	w = 1/[σ2(Fo2) + (0.0569P)2 + 1.3081P] where P = (Fo2 + 2Fc2)/3
3871 reflections	(Δ/σ)max < 0.001
163 parameters	Δρmax = 0.43 e Å−3
0 restraints	Δρmin = −0.21 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 s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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 > 2σ(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	0.131371 (14)	0.52803 (12)	0.04350 (6)	0.02016 (14)
F2	0.201443 (15)	1.06377 (13)	0.30050 (7)	0.02303 (15)
O1	0.136883 (18)	0.97437 (15)	0.36217 (7)	0.02009 (16)
N1	0.113987 (19)	1.00956 (16)	0.14156 (8)	0.01541 (16)
C1	0.16118 (2)	0.60034 (18)	0.08307 (9)	0.01554 (17)
C2	0.18629 (3)	0.4631 (2)	0.03344 (10)	0.01989 (19)
H2A	0.1826	0.3219	−0.0264	0.024*
C3	0.21695 (2)	0.5379 (2)	0.07365 (11)	0.0223 (2)
H3A	0.2346	0.4482	0.0398	0.027*
C4	0.22225 (2)	0.7422 (2)	0.16280 (11)	0.0207 (2)
H4A	0.2433	0.7941	0.1895	0.025*
C5	0.19617 (2)	0.86802 (19)	0.21155 (10)	0.01656 (18)
C6	0.16482 (2)	0.80494 (17)	0.17353 (9)	0.01396 (16)
C7	0.13715 (2)	0.93935 (17)	0.23513 (9)	0.01430 (17)
C8	0.08569 (2)	1.13880 (18)	0.17534 (9)	0.01475 (17)
C9	0.08638 (2)	1.33660 (19)	0.27115 (10)	0.01791 (18)
H9A	0.1058	1.3826	0.3189	0.021*
C10	0.05852 (2)	1.46660 (19)	0.29678 (10)	0.01816 (18)
H10A	0.0591	1.6004	0.3630	0.022*
C11	0.02971 (2)	1.40427 (18)	0.22709 (10)	0.01674 (18)
C12	0.02942 (2)	1.20383 (19)	0.13243 (11)	0.01962 (19)
H12A	0.0100	1.1570	0.0852	0.024*
C13	0.05708 (2)	1.07101 (19)	0.10588 (10)	0.01794 (18)
H13A	0.0565	0.9352	0.0409	0.022*
C14	0.0000	1.5573 (3)	0.2500	0.0213 (3)
H14A	−0.0040	1.6645	0.1702	0.026*
H1N1	0.1173 (3)	0.984 (3)	0.0566 (16)	0.023 (4)*

	U11	U22	U33	U12	U13	U23
F1	0.0186 (3)	0.0209 (3)	0.0208 (3)	−0.0022 (2)	−0.0022 (2)	−0.0022 (2)
F2	0.0207 (3)	0.0257 (3)	0.0225 (3)	−0.0035 (2)	−0.0013 (2)	−0.0072 (2)
O1	0.0220 (3)	0.0272 (4)	0.0112 (3)	0.0051 (3)	0.0022 (2)	0.0005 (3)
N1	0.0144 (3)	0.0210 (4)	0.0110 (3)	0.0032 (3)	0.0022 (3)	−0.0003 (3)
C1	0.0159 (4)	0.0180 (4)	0.0127 (4)	0.0003 (3)	0.0000 (3)	0.0020 (3)
C2	0.0249 (5)	0.0197 (5)	0.0151 (4)	0.0056 (4)	0.0019 (3)	−0.0017 (3)
C3	0.0201 (4)	0.0269 (5)	0.0202 (4)	0.0078 (4)	0.0043 (4)	0.0006 (4)
C4	0.0148 (4)	0.0268 (5)	0.0205 (4)	0.0026 (3)	0.0012 (3)	0.0017 (4)
C5	0.0168 (4)	0.0189 (4)	0.0139 (4)	−0.0001 (3)	−0.0001 (3)	−0.0001 (3)
C6	0.0146 (4)	0.0161 (4)	0.0112 (3)	0.0008 (3)	0.0011 (3)	0.0009 (3)
C7	0.0150 (4)	0.0151 (4)	0.0130 (4)	0.0003 (3)	0.0022 (3)	0.0010 (3)
C8	0.0137 (4)	0.0176 (4)	0.0132 (4)	0.0012 (3)	0.0024 (3)	0.0011 (3)
C9	0.0151 (4)	0.0220 (4)	0.0166 (4)	0.0002 (3)	0.0003 (3)	−0.0031 (3)
C10	0.0166 (4)	0.0194 (4)	0.0186 (4)	0.0005 (3)	0.0023 (3)	−0.0036 (3)
C11	0.0139 (4)	0.0158 (4)	0.0208 (4)	0.0000 (3)	0.0042 (3)	0.0014 (3)
C12	0.0145 (4)	0.0198 (4)	0.0244 (5)	−0.0008 (3)	−0.0001 (3)	−0.0023 (4)
C13	0.0166 (4)	0.0185 (4)	0.0187 (4)	0.0000 (3)	0.0004 (3)	−0.0032 (3)
C14	0.0140 (6)	0.0159 (6)	0.0343 (8)	0.000	0.0044 (5)	0.000

F1—C1	1.3489 (11)	C6—C7	1.5058 (13)
F2—C5	1.3534 (11)	C8—C9	1.3916 (13)
O1—C7	1.2297 (11)	C8—C13	1.3954 (13)
N1—C7	1.3459 (12)	C9—C10	1.3901 (13)
N1—C8	1.4222 (12)	C9—H9A	0.9500
N1—H1N1	0.842 (15)	C10—C11	1.3963 (13)
C1—C2	1.3828 (13)	C10—H10A	0.9500
C1—C6	1.3911 (13)	C11—C12	1.3952 (14)
C2—C3	1.3870 (15)	C11—C14	1.5131 (12)
C2—H2A	0.9500	C12—C13	1.3922 (13)
C3—C4	1.3899 (15)	C12—H12A	0.9500
C3—H3A	0.9500	C13—H13A	0.9500
C4—C5	1.3815 (13)	C14—C11i	1.5131 (12)
C4—H4A	0.9500	C14—H14A	0.9601
C5—C6	1.3929 (12)
C7—N1—C8	124.77 (8)	N1—C7—C6	114.80 (8)
C7—N1—H1N1	116.8 (10)	C9—C8—C13	119.99 (9)
C8—N1—H1N1	118.2 (10)	C9—C8—N1	121.25 (8)
F1—C1—C2	117.93 (9)	C13—C8—N1	118.70 (8)
F1—C1—C6	118.10 (8)	C10—C9—C8	119.73 (9)
C2—C1—C6	123.96 (9)	C10—C9—H9A	120.1
C1—C2—C3	117.96 (9)	C8—C9—H9A	120.1
C1—C2—H2A	121.0	C9—C10—C11	121.26 (9)
C3—C2—H2A	121.0	C9—C10—H10A	119.4
C2—C3—C4	120.98 (9)	C11—C10—H10A	119.4
C2—C3—H3A	119.5	C12—C11—C10	118.18 (9)
C4—C3—H3A	119.5	C12—C11—C14	121.20 (8)
C5—C4—C3	118.33 (9)	C10—C11—C14	120.57 (8)
C5—C4—H4A	120.8	C13—C12—C11	121.31 (9)
C3—C4—H4A	120.8	C13—C12—H12A	119.3
F2—C5—C4	118.12 (8)	C11—C12—H12A	119.3
F2—C5—C6	118.35 (8)	C12—C13—C8	119.51 (9)
C4—C5—C6	123.53 (9)	C12—C13—H13A	120.2
C1—C6—C5	115.22 (8)	C8—C13—H13A	120.2
C1—C6—C7	123.11 (8)	C11—C14—C11i	115.22 (11)
C5—C6—C7	121.53 (8)	C11—C14—H14A	108.5
O1—C7—N1	125.27 (9)	C11i—C14—H14A	108.4
O1—C7—C6	119.92 (8)
F1—C1—C2—C3	179.76 (9)	C5—C6—C7—O1	−46.84 (13)
C6—C1—C2—C3	−1.62 (15)	C1—C6—C7—N1	−50.49 (12)
C1—C2—C3—C4	0.95 (16)	C5—C6—C7—N1	133.95 (9)
C2—C3—C4—C5	0.57 (16)	C7—N1—C8—C9	42.34 (14)
C3—C4—C5—F2	178.73 (9)	C7—N1—C8—C13	−140.39 (10)
C3—C4—C5—C6	−1.60 (15)	C13—C8—C9—C10	−0.27 (15)
F1—C1—C6—C5	179.29 (8)	N1—C8—C9—C10	176.96 (9)
C2—C1—C6—C5	0.68 (14)	C8—C9—C10—C11	−0.61 (15)
F1—C1—C6—C7	3.47 (13)	C9—C10—C11—C12	1.22 (15)
C2—C1—C6—C7	−175.14 (9)	C9—C10—C11—C14	−176.46 (9)
F2—C5—C6—C1	−179.35 (8)	C10—C11—C12—C13	−0.98 (15)
C4—C5—C6—C1	0.98 (14)	C14—C11—C12—C13	176.68 (9)
F2—C5—C6—C7	−3.46 (13)	C11—C12—C13—C8	0.14 (15)
C4—C5—C6—C7	176.87 (9)	C9—C8—C13—C12	0.50 (15)
C8—N1—C7—O1	0.91 (16)	N1—C8—C13—C12	−176.80 (9)
C8—N1—C7—C6	−179.94 (8)	C12—C11—C14—C11i	47.96 (8)
C1—C6—C7—O1	128.72 (10)	C10—C11—C14—C11i	−134.43 (10)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N1···O1ii	0.841 (15)	2.078 (15)	2.8811 (11)	159.4 (14)
C9—H9A···F1iii	0.95	2.41	3.2318 (11)	145

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N1⋯O1i	0.841 (15)	2.078 (15)	2.8811 (11)	159.4 (14)
C9—H9A⋯F1ii	0.95	2.41	3.2318 (11)	145

Symmetry codes: (i) ; (ii) .