1,1'-Bicyclo-hexyl-1,1'-diyl 2,2'-bipyridine-3,3'-dicarboxyl-ate.

The title compound, C(24)H(26)N(2)O(4), lies about a crystallographic twofold rotation axis. The cyclo-hexane rings adopts a chair conformation. The two pyridine rings form a dihedral angle of 41.02 (4)°. In the crystal, mol-ecules are linked via C-H⋯O and C-H⋯N hydrogen bonds into a layer parallel to the bc plane.

Related literature

For the background to this study, see the first paper in this series: Fun, Quah, Wu & Zhang (2012 ▶). For a related structure, see: Fun, Quah & Wu (2012 ▶). For the stability of the temperature controller used in the the data collection, see: Cosier & Glazer (1986 ▶). For standard bond-length data, see: Allen et al. (1987 ▶). For ring conformations, see: Cremer & Pople (1975 ▶). For the preparation, see: Wu et al. (2012 ▶).

Experimental

Crystal data

C24H26N2O4

M = 406.47

Monoclinic,

a = 16.7647 (3) Å

b = 10.2618 (2) Å

c = 11.5755 (2) Å

β = 99.810 (1)°

V = 1962.28 (6) Å3

Z = 4

Mo Kα radiation

μ = 0.09 mm−1

T = 100 K

0.53 × 0.24 × 0.12 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.952, T max = 0.989

11734 measured reflections

3578 independent reflections

2972 reflections with I > 2σ(I)

R int = 0.027

Refinement

R[F 2 > 2σ(F 2)] = 0.043

wR(F 2) = 0.119

S = 1.04

3578 reflections

136 parameters

H-atom parameters constrained

Δρmax = 0.50 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/S1600536812018508/is5124sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812018508/is5124Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812018508/is5124Isup3.cml

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

C24H26N2O4	F(000) = 864
Mr = 406.47	Dx = 1.376 Mg m−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 4821 reflections
a = 16.7647 (3) Å	θ = 2.3–32.4°
b = 10.2618 (2) Å	µ = 0.09 mm−1
c = 11.5755 (2) Å	T = 100 K
β = 99.810 (1)°	Block, colourless
V = 1962.28 (6) Å3	0.53 × 0.24 × 0.12 mm
Z = 4

Bruker SMART APEXII CCD area-detector diffractometer	3578 independent reflections
Radiation source: fine-focus sealed tube	2972 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.027
φ and ω scans	θmax = 32.7°, θmin = 2.3°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −24→25
Tmin = 0.952, Tmax = 0.989	k = −15→15
11734 measured reflections	l = −14→17

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)] = 0.043	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.119	H-atom parameters constrained
S = 1.04	w = 1/[σ2(Fo2) + (0.0602P)2 + 1.2358P] where P = (Fo2 + 2Fc2)/3
3578 reflections	(Δ/σ)max = 0.001
136 parameters	Δρmax = 0.50 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
O1	0.07035 (4)	0.91569 (6)	0.32195 (5)	0.01138 (14)
O2	0.08919 (4)	0.79994 (7)	0.15933 (6)	0.01480 (15)
N1	0.03750 (5)	0.47163 (8)	0.36731 (7)	0.01641 (17)
C1	0.13527 (6)	0.68507 (10)	0.44475 (8)	0.01575 (18)
H1A	0.1678	0.7583	0.4717	0.019*
C2	0.13993 (6)	0.57190 (10)	0.51086 (8)	0.01792 (19)
H2A	0.1757	0.5658	0.5837	0.022*
C3	0.09090 (6)	0.46750 (10)	0.46771 (8)	0.01813 (19)
H3A	0.0955	0.3889	0.5117	0.022*
C4	0.03211 (5)	0.58187 (9)	0.30384 (8)	0.01315 (17)
C5	0.08212 (5)	0.68998 (9)	0.33802 (8)	0.01229 (16)
C6	0.08110 (5)	0.80731 (9)	0.26097 (8)	0.01163 (16)
C7	0.04781 (5)	1.04426 (9)	0.26757 (7)	0.01063 (16)
C8	0.09239 (5)	1.07527 (9)	0.16519 (8)	0.01365 (17)
H8A	0.0760	1.0116	0.1013	0.016*
H8B	0.0764	1.1631	0.1343	0.016*
C9	0.18467 (6)	1.07060 (10)	0.20256 (9)	0.01769 (19)
H9A	0.2013	0.9814	0.2289	0.021*
H9B	0.2110	1.0921	0.1346	0.021*
C10	0.21245 (6)	1.16711 (11)	0.30191 (9)	0.0207 (2)
H10A	0.2716	1.1591	0.3280	0.025*
H10B	0.2007	1.2572	0.2734	0.025*
C11	0.16867 (6)	1.13963 (10)	0.40464 (8)	0.01758 (19)
H11A	0.1842	1.2065	0.4660	0.021*
H11B	0.1860	1.0537	0.4388	0.021*
C12	0.07650 (5)	1.14012 (9)	0.36753 (8)	0.01346 (17)
H12A	0.0585	1.2291	0.3422	0.016*
H12B	0.0510	1.1171	0.4359	0.016*

	U11	U22	U33	U12	U13	U23
O1	0.0130 (3)	0.0087 (3)	0.0120 (3)	0.0012 (2)	0.0009 (2)	0.0006 (2)
O2	0.0162 (3)	0.0141 (3)	0.0145 (3)	0.0007 (2)	0.0040 (2)	−0.0013 (2)
N1	0.0203 (4)	0.0111 (4)	0.0178 (3)	0.0014 (3)	0.0030 (3)	0.0021 (3)
C1	0.0156 (4)	0.0141 (4)	0.0164 (4)	0.0025 (3)	−0.0004 (3)	−0.0002 (3)
C2	0.0196 (4)	0.0177 (5)	0.0154 (4)	0.0054 (4)	−0.0002 (3)	0.0016 (3)
C3	0.0223 (4)	0.0140 (4)	0.0180 (4)	0.0052 (4)	0.0032 (3)	0.0039 (3)
C4	0.0156 (4)	0.0099 (4)	0.0138 (4)	0.0012 (3)	0.0022 (3)	0.0001 (3)
C5	0.0132 (3)	0.0097 (4)	0.0139 (3)	0.0020 (3)	0.0020 (3)	0.0005 (3)
C6	0.0094 (3)	0.0098 (4)	0.0151 (4)	−0.0001 (3)	0.0003 (3)	−0.0002 (3)
C7	0.0118 (3)	0.0076 (3)	0.0119 (3)	−0.0002 (3)	0.0003 (3)	0.0009 (3)
C8	0.0132 (4)	0.0137 (4)	0.0140 (4)	−0.0011 (3)	0.0023 (3)	0.0021 (3)
C9	0.0134 (4)	0.0198 (5)	0.0203 (4)	−0.0020 (3)	0.0040 (3)	0.0032 (4)
C10	0.0143 (4)	0.0193 (5)	0.0271 (5)	−0.0050 (4)	−0.0001 (3)	0.0018 (4)
C11	0.0141 (4)	0.0167 (4)	0.0200 (4)	−0.0014 (3)	−0.0028 (3)	−0.0025 (4)
C12	0.0142 (4)	0.0101 (4)	0.0148 (4)	−0.0005 (3)	−0.0011 (3)	−0.0023 (3)

O1—C6	1.3458 (11)	C7—C7i	1.5854 (17)
O1—C7	1.4828 (11)	C8—C9	1.5344 (13)
O2—C6	1.2094 (11)	C8—H8A	0.9900
N1—C3	1.3414 (12)	C8—H8B	0.9900
N1—C4	1.3435 (12)	C9—C10	1.5290 (15)
C1—C2	1.3856 (14)	C9—H9A	0.9900
C1—C5	1.3956 (12)	C9—H9B	0.9900
C1—H1A	0.9500	C10—C11	1.5264 (15)
C2—C3	1.3903 (15)	C10—H10A	0.9900
C2—H2A	0.9500	C10—H10B	0.9900
C3—H3A	0.9500	C11—C12	1.5317 (13)
C4—C5	1.4061 (13)	C11—H11A	0.9900
C4—C4i	1.5018 (18)	C11—H11B	0.9900
C5—C6	1.4968 (12)	C12—H12A	0.9900
C7—C12	1.5324 (12)	C12—H12B	0.9900
C7—C8	1.5382 (12)
C6—O1—C7	124.05 (6)	C7—C8—H8A	109.2
C3—N1—C4	118.24 (9)	C9—C8—H8B	109.2
C2—C1—C5	119.12 (9)	C7—C8—H8B	109.2
C2—C1—H1A	120.4	H8A—C8—H8B	107.9
C5—C1—H1A	120.4	C10—C9—C8	110.80 (8)
C1—C2—C3	118.24 (9)	C10—C9—H9A	109.5
C1—C2—H2A	120.9	C8—C9—H9A	109.5
C3—C2—H2A	120.9	C10—C9—H9B	109.5
N1—C3—C2	123.60 (9)	C8—C9—H9B	109.5
N1—C3—H3A	118.2	H9A—C9—H9B	108.1
C2—C3—H3A	118.2	C11—C10—C9	109.94 (8)
N1—C4—C5	121.94 (8)	C11—C10—H10A	109.7
N1—C4—C4i	115.20 (6)	C9—C10—H10A	109.7
C5—C4—C4i	122.84 (6)	C11—C10—H10B	109.7
C1—C5—C4	118.74 (8)	C9—C10—H10B	109.7
C1—C5—C6	119.82 (8)	H10A—C10—H10B	108.2
C4—C5—C6	121.42 (8)	C10—C11—C12	112.15 (8)
O2—C6—O1	127.53 (8)	C10—C11—H11A	109.2
O2—C6—C5	122.52 (8)	C12—C11—H11A	109.2
O1—C6—C5	109.95 (7)	C10—C11—H11B	109.2
O1—C7—C12	103.07 (6)	C12—C11—H11B	109.2
O1—C7—C8	112.90 (7)	H11A—C11—H11B	107.9
C12—C7—C8	108.53 (7)	C11—C12—C7	112.42 (8)
O1—C7—C7i	106.40 (5)	C11—C12—H12A	109.1
C12—C7—C7i	111.54 (7)	C7—C12—H12A	109.1
C8—C7—C7i	113.91 (8)	C11—C12—H12B	109.1
C9—C8—C7	112.04 (7)	C7—C12—H12B	109.1
C9—C8—H8A	109.2	H12A—C12—H12B	107.9
C5—C1—C2—C3	−0.15 (14)	C1—C5—C6—O1	−53.79 (11)
C4—N1—C3—C2	1.26 (15)	C4—C5—C6—O1	128.11 (9)
C1—C2—C3—N1	−2.13 (16)	C6—O1—C7—C12	−157.78 (7)
C3—N1—C4—C5	1.90 (14)	C6—O1—C7—C8	−40.90 (10)
C3—N1—C4—C4i	−176.74 (10)	C6—O1—C7—C7i	84.75 (10)
C2—C1—C5—C4	3.07 (14)	O1—C7—C8—C9	−56.99 (10)
C2—C1—C5—C6	−175.08 (8)	C12—C7—C8—C9	56.61 (10)
N1—C4—C5—C1	−4.06 (14)	C7i—C7—C8—C9	−178.48 (6)
C4i—C4—C5—C1	174.47 (10)	C7—C8—C9—C10	−58.49 (11)
N1—C4—C5—C6	174.05 (8)	C8—C9—C10—C11	56.01 (11)
C4i—C4—C5—C6	−7.41 (15)	C9—C10—C11—C12	−54.88 (11)
C7—O1—C6—O2	14.66 (13)	C10—C11—C12—C7	55.67 (11)
C7—O1—C6—C5	−165.46 (7)	O1—C7—C12—C11	65.03 (9)
C1—C5—C6—O2	126.10 (10)	C8—C7—C12—C11	−54.90 (10)
C4—C5—C6—O2	−52.00 (13)	C7i—C7—C12—C11	178.81 (7)

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3A···O2ii	0.95	2.60	3.5319 (12)	168
C12—H12A···N1iii	0.99	2.54	3.4641 (12)	156

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C3—H3A⋯O2i	0.95	2.60	3.5319 (12)	168
C12—H12A⋯N1ii	0.99	2.54	3.4641 (12)	156

Symmetry codes: (i) ; (ii) .