Di-tert-butyl 3,3'-(2,2'-bi-1H-imidazole-1,1'-di-yl)dipropanoate.

In the title compound, C(20)H(20)N(4)O(4), the complete molecule is generated by a crystallographic centre of symmetry. The conformation is stabilized by two intramolecular C-H⋯N links.

Related literature

For the background to 2, 2′-biimidazole derivatives, see: Barnett et al. (1999 ▶, 2002 ▶); Liang et al. (2009 ▶); Zhang & Liang (2009 ▶); Zhang, Zhang, Ren et al. (2009 ▶); Zhang, Zhang, Xu et al. (2009 ▶). For the synthesis, see: Barnett et al. (1999 ▶).

Experimental

Crystal data

C20H30N4O4

M = 390.48

Monoclinic,

a = 7.0321 (14) Å

b = 17.484 (4) Å

c = 8.9681 (18) Å

β = 100.80 (3)°

V = 1083.1 (4) Å3

Z = 2

Mo Kα radiation

μ = 0.08 mm−1

T = 295 K

0.48 × 0.42 × 0.14 mm

Data collection

Rigaku R-AXIS RAPID diffractometer

Absorption correction: multi-scan (ABSCOR; Higashi, 1995 ▶) T min = 0.960, T max = 0.988

9620 measured reflections

2453 independent reflections

1474 reflections with I > 2σ(I)

R int = 0.077

Refinement

R[F 2 > 2σ(F 2)] = 0.077

wR(F 2) = 0.190

S = 1.02

2453 reflections

128 parameters

H-atom parameters constrained

Δρmax = 0.32 e Å−3

Δρmin = −0.24 e Å−3

Data collection: RAPID-AUTO (Rigaku, 1998 ▶); cell refinement: RAPID-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2004 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809021369/fb2148sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809021369/fb2148Isup2.hkl

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

C20H30N4O4	F(000) = 420
Mr = 390.48	Dx = 1.197 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 1478 reflections
a = 7.0321 (14) Å	θ = 3.0–27.5°
b = 17.484 (4) Å	µ = 0.08 mm−1
c = 8.9681 (18) Å	T = 295 K
β = 100.80 (3)°	Plate, colourless
V = 1083.1 (4) Å3	0.48 × 0.42 × 0.14 mm
Z = 2

Rigaku R-AXIS RAPID diffractometer	2453 independent reflections
Radiation source: fine-focus sealed tube	1474 reflections with I > 2σ(I)
graphite	Rint = 0.077
Detector resolution: 0 pixels mm-1	θmax = 27.5°, θmin = 3.2°
ω scans	h = −9→9
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	k = −22→22
Tmin = 0.960, Tmax = 0.988	l = −11→10
9620 measured reflections

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)] = 0.077	Hydrogen site location: difference Fourier map
wR(F2) = 0.190	H-atom parameters constrained
S = 1.02	w = 1/[σ2(Fo2) + (0.0718P)2 + 0.3943P] where P = (Fo2 + 2Fc2)/3
2453 reflections	(Δ/σ)max < 0.001
128 parameters	Δρmax = 0.32 e Å−3
0 restraints	Δρmin = −0.24 e Å−3
59 constraints

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
N1	0.3460 (3)	0.51573 (11)	0.30746 (19)	0.0410 (5)
N2	0.6689 (3)	0.51901 (13)	0.3698 (2)	0.0522 (6)
C10	0.1400 (3)	0.50398 (14)	0.3101 (3)	0.0454 (6)
H10A	0.0628	0.5297	0.2237	0.054*
H10B	0.1099	0.5268	0.4016	0.054*
O2	0.2468 (3)	0.32667 (12)	0.1854 (2)	0.0717 (6)
O1	0.0366 (3)	0.40123 (12)	0.0365 (2)	0.0774 (7)
C9	0.5051 (3)	0.50815 (13)	0.4210 (2)	0.0415 (6)
C8	0.1171 (4)	0.38275 (15)	0.1612 (3)	0.0525 (6)
C7	0.6104 (4)	0.53329 (17)	0.2169 (3)	0.0568 (7)
H7A	0.6939	0.5428	0.1501	0.068*
C6	0.4159 (4)	0.53160 (15)	0.1774 (2)	0.0504 (6)
H6A	0.3431	0.5396	0.0809	0.061*
C5	0.0864 (4)	0.41992 (15)	0.3056 (3)	0.0520 (6)
H5A	0.1644	0.3940	0.3914	0.062*
H5B	−0.0484	0.4147	0.3144	0.062*
C4	0.2854 (6)	0.2868 (2)	0.0492 (4)	0.0905 (11)
H4A	0.3139	0.3238	−0.0242	0.109*
H4B	0.1724	0.2577	0.0027	0.109*
C3	0.4524 (6)	0.2349 (2)	0.0943 (5)	0.0958 (12)
H3A	0.4239	0.2005	0.1722	0.115*
H3B	0.4664	0.2039	0.0072	0.115*
C2	0.6387 (6)	0.2728 (2)	0.1520 (5)	0.1045 (13)
H2B	0.6290	0.3010	0.2434	0.125*
H2C	0.6653	0.3092	0.0770	0.125*
C1	0.8074 (6)	0.2163 (3)	0.1876 (7)	0.1289 (18)
H1A	0.9241	0.2435	0.2285	0.193*
H1B	0.8229	0.1904	0.0962	0.193*
H1C	0.7809	0.1795	0.2605	0.193*

	U11	U22	U33	U12	U13	U23
N1	0.0380 (10)	0.0516 (11)	0.0319 (9)	0.0030 (9)	0.0030 (7)	0.0023 (8)
N2	0.0407 (11)	0.0834 (16)	0.0336 (10)	0.0013 (10)	0.0097 (8)	0.0031 (10)
C10	0.0364 (11)	0.0564 (15)	0.0413 (12)	0.0045 (11)	0.0017 (9)	0.0019 (10)
O2	0.0728 (13)	0.0805 (15)	0.0564 (12)	0.0151 (11)	−0.0018 (9)	−0.0074 (10)
O1	0.0988 (16)	0.0791 (15)	0.0457 (11)	0.0097 (12)	−0.0087 (10)	0.0001 (9)
C9	0.0377 (11)	0.0553 (14)	0.0304 (11)	0.0037 (11)	0.0033 (8)	−0.0010 (9)
C8	0.0518 (14)	0.0532 (15)	0.0491 (15)	−0.0082 (12)	0.0006 (11)	0.0019 (11)
C7	0.0522 (15)	0.086 (2)	0.0343 (12)	−0.0015 (13)	0.0134 (10)	0.0047 (12)
C6	0.0539 (14)	0.0675 (17)	0.0289 (11)	0.0016 (12)	0.0051 (10)	0.0033 (11)
C5	0.0474 (13)	0.0629 (16)	0.0444 (13)	−0.0046 (12)	0.0054 (10)	0.0044 (12)
C4	0.100 (3)	0.098 (3)	0.069 (2)	0.020 (2)	0.0058 (18)	−0.0199 (19)
C3	0.097 (3)	0.095 (3)	0.098 (3)	−0.005 (2)	0.026 (2)	−0.021 (2)
C2	0.101 (3)	0.095 (3)	0.115 (3)	−0.006 (2)	0.013 (2)	−0.001 (2)
C1	0.087 (3)	0.101 (3)	0.198 (5)	0.000 (2)	0.025 (3)	0.031 (3)

N1—C9	1.371 (3)	C6—H6A	0.9300
N1—C6	1.376 (3)	C5—H5A	0.9700
N1—C10	1.468 (3)	C5—H5B	0.9700
N2—C9	1.331 (3)	C4—C3	1.480 (5)
N2—C7	1.378 (3)	C4—H4A	0.9700
C10—C5	1.516 (3)	C4—H4B	0.9700
C10—H10A	0.9700	C3—C2	1.473 (5)
C10—H10B	0.9700	C3—H3A	0.9700
O2—C8	1.329 (3)	C3—H3B	0.9700
O2—C4	1.475 (4)	C2—C1	1.531 (5)
O1—C8	1.199 (3)	C2—H2B	0.9700
C9—C9i	1.460 (4)	C2—H2C	0.9700
C8—C5	1.500 (4)	C1—H1A	0.9600
C7—C6	1.347 (3)	C1—H1B	0.9600
C7—H7A	0.9300	C1—H1C	0.9600
C9—N1—C6	106.13 (18)	C10—C5—H5B	109.3
C9—N1—C10	130.15 (19)	H5A—C5—H5B	108.0
C6—N1—C10	123.53 (18)	O2—C4—C3	108.9 (3)
C9—N2—C7	104.6 (2)	O2—C4—H4A	109.9
N1—C10—C5	112.1 (2)	C3—C4—H4A	109.9
N1—C10—H10A	109.2	O2—C4—H4B	109.9
C5—C10—H10A	109.2	C3—C4—H4B	109.9
N1—C10—H10B	109.2	H4A—C4—H4B	108.3
C5—C10—H10B	109.2	C2—C3—C4	115.3 (4)
H10A—C10—H10B	107.9	C2—C3—H3A	108.4
C8—O2—C4	116.1 (2)	C4—C3—H3A	108.4
N2—C9—N1	111.59 (19)	C2—C3—H3B	108.4
N2—C9—C9i	124.5 (2)	C4—C3—H3B	108.4
N1—C9—C9i	123.9 (2)	H3A—C3—H3B	107.5
O1—C8—O2	122.7 (3)	C3—C2—C1	112.7 (4)
O1—C8—C5	124.7 (3)	C3—C2—H2B	109.0
O2—C8—C5	112.6 (2)	C1—C2—H2B	109.0
C6—C7—N2	110.9 (2)	C3—C2—H2C	109.0
C6—C7—H7A	124.5	C1—C2—H2C	109.0
N2—C7—H7A	124.5	H2B—C2—H2C	107.8
C7—C6—N1	106.7 (2)	C2—C1—H1A	109.5
C7—C6—H6A	126.6	C2—C1—H1B	109.5
N1—C6—H6A	126.6	H1A—C1—H1B	109.5
C8—C5—C10	111.6 (2)	C2—C1—H1C	109.5
C8—C5—H5A	109.3	H1A—C1—H1C	109.5
C10—C5—H5A	109.3	H1B—C1—H1C	109.5
C8—C5—H5B	109.3

D—H···A	D—H	H···A	D···A	D—H···A
C10—H10B···N2i	0.97	2.46	2.960 (3)	111

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C10—H10B⋯N2i	0.97	2.46	2.960 (3)	111

Symmetry code: (i) .