N,N'-Diphenyl-suberamide.

IN THE TITLE COMPOUND (SYSTEMATIC NAME: N,N'-diphenyl-octanediamide), C(20)H(24)N(2)O(2), the two phenyl rings make an inter-planar angle of 76.5 (2)°. The crystal structure is stabilized by inter-molecular N-H⋯O hydrogen bonds, which link the mol-ecules into chains running along the b axis. The crystal studied was non-merohedrally twinned, the fractional contribution of the minor twin component being 0.203 (2).

Related literature

For related structures, see: Gowda et al. (2007 ▶, 2009 ▶).

Experimental

Crystal data

C20H24N2O2

M = 324.41

Monoclinic,

a = 18.2267 (9) Å

b = 5.03097 (15) Å

c = 38.1436 (15) Å

β = 96.517 (4)°

V = 3475.1 (2) Å3

Z = 8

Mo Kα radiation

μ = 0.08 mm−1

T = 295 K

0.58 × 0.33 × 0.05 mm

Data collection

Oxford Diffraction Gemini R CCD diffractometer

Absorption correction: analytical (CrysAlis PRO; Oxford Diffraction, 2009 ▶) T min = 0.957, T max = 0.996

27788 measured reflections

3027 independent reflections

2524 reflections with I > 2σ(I)

R int = 0.064

Refinement

R[F 2 > 2σ(F 2)] = 0.076

wR(F 2) = 0.203

S = 1.09

3027 reflections

224 parameters

2 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.21 e Å−3

Δρmin = −0.22 e Å−3

Data collection: CrysAlis PRO (Oxford Diffraction, 2009 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶) and DIAMOND (Brandenburg, 2002 ▶); software used to prepare material for publication: SHELXL97, PLATON (Spek, 2009 ▶) and WinGX (Farrugia, 1999 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810017344/bt5267sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810017344/bt5267Isup2.hkl

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

C20H24N2O2	F(000) = 1392
Mr = 324.41	Dx = 1.24 Mg m−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 7864 reflections
a = 18.2267 (9) Å	θ = 1.9–27.4°
b = 5.03097 (15) Å	µ = 0.08 mm−1
c = 38.1436 (15) Å	T = 295 K
β = 96.517 (4)°	Plate, colourless
V = 3475.1 (2) Å3	0.58 × 0.33 × 0.05 mm
Z = 8

Oxford Diffraction Gemini R CCD diffractometer	3027 independent reflections
graphite	2524 reflections with I > 2σ(I)
Detector resolution: 10.434 pixels mm-1	Rint = 0.064
ω scans	θmax = 25.0°, θmin = 2.2°
Absorption correction: analytical (CrysAlis PRO; Oxford Diffraction, 2009)	h = −21→21
Tmin = 0.957, Tmax = 0.996	k = −5→5
27788 measured reflections	l = −45→45

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)] = 0.076	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.203	H atoms treated by a mixture of independent and constrained refinement
S = 1.09	w = 1/[σ2(Fo2) + (0.0865P)2 + 8.373P] where P = (Fo2 + 2Fc2)/3
3027 reflections	(Δ/σ)max < 0.001
224 parameters	Δρmax = 0.21 e Å−3
2 restraints	Δρmin = −0.22 e Å−3

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
C1	0.0479 (2)	0.3940 (7)	0.55627 (10)	0.0357 (9)
C2	0.0772 (2)	0.2805 (8)	0.52403 (10)	0.0392 (9)
H2A	0.0358	0.2378	0.5067	0.047*
H2B	0.1029	0.1158	0.5306	0.047*
C3	0.1291 (2)	0.4621 (8)	0.50714 (10)	0.0398 (9)
H3A	0.1732	0.489	0.5235	0.048*
H3B	0.1055	0.6337	0.5028	0.048*
C4	0.1511 (2)	0.3560 (8)	0.47276 (10)	0.0398 (9)
H4A	0.1068	0.3257	0.4567	0.048*
H4B	0.1754	0.1857	0.4772	0.048*
C5	0.2020 (2)	0.5373 (8)	0.45507 (9)	0.0415 (10)
H5A	0.247	0.5627	0.4709	0.05*
H5B	0.1784	0.7095	0.4514	0.05*
C6	0.2222 (2)	0.4363 (8)	0.42003 (10)	0.0417 (10)
H6A	0.2457	0.2638	0.4235	0.05*
H6B	0.1775	0.4133	0.404	0.05*
C7	0.2735 (2)	0.6215 (8)	0.40346 (10)	0.0416 (10)
H7A	0.3186	0.6418	0.4194	0.05*
H7B	0.2505	0.795	0.4004	0.05*
C8	0.2930 (2)	0.5254 (7)	0.36811 (10)	0.0388 (9)
C9	−0.0140 (2)	0.2611 (7)	0.60821 (9)	0.0343 (8)
C10	−0.0691 (2)	0.0877 (9)	0.61530 (10)	0.0459 (10)
H10	−0.0822	−0.0522	0.5999	0.055*
C11	−0.1051 (3)	0.1199 (10)	0.64514 (11)	0.0565 (12)
H11	−0.1425	0.0034	0.6497	0.068*
C12	−0.0851 (3)	0.3247 (10)	0.66783 (11)	0.0595 (13)
H12	−0.109	0.3482	0.6879	0.071*
C13	−0.0299 (3)	0.4945 (9)	0.66109 (10)	0.0574 (12)
H13	−0.0168	0.633	0.6767	0.069*
C14	0.0070 (2)	0.4649 (8)	0.63144 (10)	0.0439 (10)
H14	0.0451	0.5798	0.6273	0.053*
C15	0.3338 (2)	0.6863 (7)	0.31213 (10)	0.0382 (9)
C16	0.3837 (2)	0.4959 (9)	0.30577 (11)	0.0517 (11)
H16	0.401	0.3772	0.3235	0.062*
C17	0.4088 (3)	0.4791 (11)	0.27288 (13)	0.0676 (14)
H17	0.4425	0.3479	0.2685	0.081*
C18	0.3837 (3)	0.6570 (11)	0.24667 (12)	0.0695 (15)
H18	0.4011	0.6476	0.2247	0.083*
C19	0.3336 (3)	0.8462 (11)	0.25299 (13)	0.0738 (16)
H19	0.3157	0.9633	0.2352	0.089*
C20	0.3091 (3)	0.8644 (9)	0.28602 (12)	0.0565 (12)
H20	0.2759	0.9971	0.2905	0.068*
N1	0.02190 (19)	0.2112 (6)	0.57763 (8)	0.0381 (8)
H1N	0.029 (2)	0.055 (6)	0.5713 (11)	0.046*
N2	0.3100 (2)	0.7191 (6)	0.34624 (9)	0.0405 (8)
H2N	0.302 (2)	0.868 (6)	0.3547 (11)	0.049*
O1	0.04456 (18)	0.6348 (5)	0.56139 (8)	0.0503 (8)
O2	0.2948 (2)	0.2890 (6)	0.36057 (9)	0.0652 (10)

	U11	U22	U33	U12	U13	U23
C1	0.041 (2)	0.029 (2)	0.038 (2)	0.0025 (17)	0.0096 (17)	−0.0019 (17)
C2	0.050 (2)	0.032 (2)	0.038 (2)	−0.0012 (18)	0.0144 (18)	−0.0054 (17)
C3	0.046 (2)	0.037 (2)	0.038 (2)	−0.0056 (18)	0.0141 (17)	−0.0075 (17)
C4	0.044 (2)	0.038 (2)	0.039 (2)	−0.0018 (18)	0.0125 (17)	−0.0048 (17)
C5	0.052 (2)	0.038 (2)	0.037 (2)	−0.0057 (19)	0.0163 (18)	−0.0080 (18)
C6	0.055 (2)	0.031 (2)	0.042 (2)	−0.0081 (18)	0.0166 (19)	−0.0062 (17)
C7	0.051 (2)	0.033 (2)	0.042 (2)	−0.0046 (19)	0.0131 (19)	−0.0038 (18)
C8	0.050 (2)	0.026 (2)	0.044 (2)	−0.0011 (18)	0.0215 (19)	−0.0072 (17)
C9	0.039 (2)	0.0295 (19)	0.0347 (19)	0.0036 (17)	0.0069 (16)	0.0021 (15)
C10	0.057 (3)	0.043 (2)	0.039 (2)	−0.007 (2)	0.0131 (19)	−0.0037 (18)
C11	0.060 (3)	0.058 (3)	0.056 (3)	0.002 (2)	0.029 (2)	0.011 (2)
C12	0.079 (3)	0.062 (3)	0.042 (2)	0.013 (3)	0.030 (2)	0.005 (2)
C13	0.089 (3)	0.047 (3)	0.037 (2)	0.005 (3)	0.011 (2)	−0.009 (2)
C14	0.051 (2)	0.040 (2)	0.041 (2)	−0.0034 (19)	0.0109 (19)	−0.0051 (19)
C15	0.046 (2)	0.030 (2)	0.041 (2)	−0.0092 (17)	0.0134 (18)	−0.0034 (17)
C16	0.060 (3)	0.049 (2)	0.050 (2)	0.008 (2)	0.021 (2)	0.002 (2)
C17	0.081 (3)	0.060 (3)	0.070 (3)	0.005 (3)	0.042 (3)	−0.009 (3)
C18	0.102 (4)	0.066 (3)	0.046 (3)	−0.018 (3)	0.035 (3)	−0.009 (3)
C19	0.113 (5)	0.063 (3)	0.047 (3)	−0.005 (3)	0.019 (3)	0.013 (3)
C20	0.072 (3)	0.042 (3)	0.058 (3)	0.002 (2)	0.017 (2)	0.004 (2)
N1	0.0527 (19)	0.0262 (16)	0.0384 (17)	−0.0009 (15)	0.0174 (15)	−0.0018 (14)
N2	0.054 (2)	0.0263 (17)	0.0446 (19)	−0.0037 (15)	0.0198 (16)	−0.0016 (15)
O1	0.072 (2)	0.0293 (15)	0.0548 (18)	0.0002 (14)	0.0316 (16)	−0.0006 (13)
O2	0.110 (3)	0.0280 (16)	0.067 (2)	−0.0056 (17)	0.051 (2)	−0.0043 (14)

C1—O1	1.229 (5)	C9—N1	1.423 (5)
C1—N1	1.350 (5)	C10—C11	1.386 (6)
C1—C2	1.508 (5)	C10—H10	0.93
C2—C3	1.510 (5)	C11—C12	1.368 (7)
C2—H2A	0.97	C11—H11	0.93
C2—H2B	0.97	C12—C13	1.366 (7)
C3—C4	1.512 (5)	C12—H12	0.93
C3—H3A	0.97	C13—C14	1.388 (6)
C3—H3B	0.97	C13—H13	0.93
C4—C5	1.513 (5)	C14—H14	0.93
C4—H4A	0.97	C15—C16	1.362 (6)
C4—H4B	0.97	C15—C20	1.377 (6)
C5—C6	1.514 (5)	C15—N2	1.427 (5)
C5—H5A	0.97	C16—C17	1.385 (6)
C5—H5B	0.97	C16—H16	0.93
C6—C7	1.509 (5)	C17—C18	1.381 (7)
C6—H6A	0.97	C17—H17	0.93
C6—H6B	0.97	C18—C19	1.360 (8)
C7—C8	1.512 (5)	C18—H18	0.93
C7—H7A	0.97	C19—C20	1.387 (7)
C7—H7B	0.97	C19—H19	0.93
C8—O2	1.225 (5)	C20—H20	0.93
C8—N2	1.342 (5)	N1—H1N	0.84 (3)
C9—C10	1.380 (6)	N2—H2N	0.84 (3)
C9—C14	1.381 (5)
O1—C1—N1	123.3 (3)	C10—C9—C14	119.9 (3)
O1—C1—C2	122.1 (3)	C10—C9—N1	117.5 (3)
N1—C1—C2	114.5 (3)	C14—C9—N1	122.5 (3)
C1—C2—C3	114.6 (3)	C9—C10—C11	120.7 (4)
C1—C2—H2A	108.6	C9—C10—H10	119.7
C3—C2—H2A	108.6	C11—C10—H10	119.7
C1—C2—H2B	108.6	C12—C11—C10	119.3 (4)
C3—C2—H2B	108.6	C12—C11—H11	120.3
H2A—C2—H2B	107.6	C10—C11—H11	120.3
C2—C3—C4	113.4 (3)	C13—C12—C11	120.1 (4)
C2—C3—H3A	108.9	C13—C12—H12	119.9
C4—C3—H3A	108.9	C11—C12—H12	119.9
C2—C3—H3B	108.9	C12—C13—C14	121.4 (4)
C4—C3—H3B	108.9	C12—C13—H13	119.3
H3A—C3—H3B	107.7	C14—C13—H13	119.3
C3—C4—C5	114.2 (3)	C9—C14—C13	118.5 (4)
C3—C4—H4A	108.7	C9—C14—H14	120.7
C5—C4—H4A	108.7	C13—C14—H14	120.7
C3—C4—H4B	108.7	C16—C15—C20	120.0 (4)
C5—C4—H4B	108.7	C16—C15—N2	121.5 (4)
H4A—C4—H4B	107.6	C20—C15—N2	118.4 (4)
C4—C5—C6	114.5 (3)	C15—C16—C17	120.0 (4)
C4—C5—H5A	108.6	C15—C16—H16	120
C6—C5—H5A	108.6	C17—C16—H16	120
C4—C5—H5B	108.6	C18—C17—C16	120.0 (5)
C6—C5—H5B	108.6	C18—C17—H17	120
H5A—C5—H5B	107.6	C16—C17—H17	120
C7—C6—C5	112.8 (3)	C19—C18—C17	119.9 (4)
C7—C6—H6A	109	C19—C18—H18	120
C5—C6—H6A	109	C17—C18—H18	120
C7—C6—H6B	109	C18—C19—C20	120.0 (5)
C5—C6—H6B	109	C18—C19—H19	120
H6A—C6—H6B	107.8	C20—C19—H19	120
C6—C7—C8	113.3 (3)	C15—C20—C19	120.1 (5)
C6—C7—H7A	108.9	C15—C20—H20	119.9
C8—C7—H7A	108.9	C19—C20—H20	119.9
C6—C7—H7B	108.9	C1—N1—C9	126.9 (3)
C8—C7—H7B	108.9	C1—N1—H1N	113 (3)
H7A—C7—H7B	107.7	C9—N1—H1N	120 (3)
O2—C8—N2	123.0 (4)	C8—N2—C15	126.8 (3)
O2—C8—C7	122.3 (4)	C8—N2—H2N	110 (3)
N2—C8—C7	114.6 (3)	C15—N2—H2N	123 (3)
O1—C1—C2—C3	23.9 (6)	C20—C15—C16—C17	−0.9 (7)
N1—C1—C2—C3	−159.8 (3)	N2—C15—C16—C17	−176.4 (4)
C1—C2—C3—C4	−173.8 (3)	C15—C16—C17—C18	0.7 (8)
C2—C3—C4—C5	179.0 (4)	C16—C17—C18—C19	−1.0 (8)
C3—C4—C5—C6	−178.1 (4)	C17—C18—C19—C20	1.7 (8)
C4—C5—C6—C7	−179.4 (4)	C16—C15—C20—C19	1.5 (7)
C5—C6—C7—C8	−178.9 (4)	N2—C15—C20—C19	177.1 (4)
C6—C7—C8—O2	−29.1 (6)	C18—C19—C20—C15	−1.9 (8)
C6—C7—C8—N2	152.7 (4)	O1—C1—N1—C9	1.5 (7)
C14—C9—C10—C11	1.7 (6)	C2—C1—N1—C9	−174.8 (4)
N1—C9—C10—C11	178.2 (4)	C10—C9—N1—C1	145.5 (4)
C9—C10—C11—C12	−0.6 (7)	C14—C9—N1—C1	−38.0 (6)
C10—C11—C12—C13	−0.2 (7)	O2—C8—N2—C15	−1.4 (7)
C11—C12—C13—C14	0.0 (7)	C7—C8—N2—C15	176.8 (4)
C10—C9—C14—C13	−2.0 (6)	C16—C15—N2—C8	−42.2 (6)
N1—C9—C14—C13	−178.3 (4)	C20—C15—N2—C8	142.3 (4)
C12—C13—C14—C9	1.1 (7)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O1i	0.84 (3)	2.17 (3)	3.004 (4)	173 (4)
N2—H2N···O2ii	0.84 (3)	2.13 (3)	2.937 (4)	161 (4)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯O1i	0.84 (3)	2.17 (3)	3.004 (4)	173 (4)
N2—H2N⋯O2ii	0.84 (3)	2.13 (3)	2.937 (4)	161 (4)

Symmetry codes: (i) ; (ii) .