Diethyl 2,2′-bi­pyridine-4,4′-di­carboxyl­ate

The title bi­pyridine derivative, C₁₆H₁₆N₂O₄, crystallized with two half mol­ecules in the asymmetric unit. The whole mol­ecules (A and B) are generated by inversion symmetry with the mid-points of the bridging C—C bonds of the bi­pyridine units being located on crystallographic inversion centers. In the crystal, mol­ecules are linked by C—H...O hydrogen bonds, forming sheets parallel to (120). The sheets are linked by C—H...N hydrogen bonds, forming a three-dimensional framework.

Key indicators

• Single-crystal X-ray study
• T = 100 K
• Mean [sigma](C-C) = 0.004 Å
• R factor = 0.057
• wR factor = 0.141
• Data-to-parameter ratio = 13.3

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT094_ALERT_2_C Ratio of Maximum / Minimum Residual Density ....       2.27 Report
PLAT230_ALERT_2_C Hirshfeld Test Diff for    O2'    --  C7'     ..        7.0 s.u.
PLAT906_ALERT_3_C Large K value in the Analysis of Variance ......     12.209 Check
PLAT911_ALERT_3_C Missing # FCF Refl Between THmin & STh/L=  0.600          8 Report
PLAT978_ALERT_2_C Number C-C Bonds with Positive Residual Density           0 Note

Alert level G
PLAT154_ALERT_1_G The s.u.'s on the Cell Angles are Equal ..(Note)      0.007 Degree
PLAT720_ALERT_4_G Number of Unusual/Non-Standard Labels ..........          5 Note
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L=  0.600          3 Note

   0 ALERT level A = Most likely a serious problem - resolve or explain
   0 ALERT level B = A potentially serious problem, consider carefully
   5 ALERT level C = Check. Ensure it is not caused by an omission or oversight
   3 ALERT level G = General information/check it is not something unexpected

   1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   3 ALERT type 2 Indicator that the structure model may be wrong or deficient
   2 ALERT type 3 Indicator that the structure quality may be low
   2 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

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Computing details

Data collection: APEX2 (Bruker, 2013); cell refinement: SAINT (Bruker, 2013); data reduction: SAINT (Bruker, 2013); program(s) used to solve structure: SHEXLS2014 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015); molecular graphics: OLEX2 (Dolomanov et al., 2009) and Mercury (Macrae et al., 2008); software used to prepare material for publication: OLEX2 (Dolomanov et al., 2009).

Diethyl 2,2'-bipyridine-4,4'-dicarboxylate

Crystal data

C16H16N2O4	Z = 2
Mr = 300.31	F(000) = 316
Triclinic, P1	Dx = 1.380 Mg m^−3
a = 3.9059 (8) Å	Mo Kα radiation, λ = 0.71073 Å
b = 13.493 (3) Å	Cell parameters from 2248 reflections
c = 13.767 (3) Å	θ = 3.0–25.0°
α = 92.212 (7)°	µ = 0.10 mm^−1
β = 93.163 (7)°	T = 100 K
γ = 93.016 (7)°	Plate, colorless
V = 722.8 (3) Å^3	0.13 × 0.08 × 0.06 mm

Data collection

Bruker APEXII Ultra diffractometer	2664 independent reflections
Radiation source: Micro Focus Rotating Anode, Bruker TXS	1699 reflections with I > 2σ(I)
Double Bounce Multilayer Mirrors monochromator	Rint = 0.054
Detector resolution: 7.9 pixels mm^-1	θmax = 25.4°, θmin = 1.5°
ω and φ scans	h = −4→4
Absorption correction: multi-scan (SADABS; Bruker, 2013)	k = −16→16
Tmin = 0.066, Tmax = 0.092	l = −16→16
10150 measured reflections

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.057	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.141	H-atom parameters constrained
S = 1.02	w = 1/[σ^2(Fo^2) + (0.0623P)^2 + 0.352P] where P = (Fo^2 + 2Fc^2)/3
2664 reflections	(Δ/σ)max < 0.001
201 parameters	Δρmax = 0.59 e Å^−3
0 restraints	Δρmin = −0.26 e Å^−3

Special details

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
N1	0.6443 (6)	−0.08269 (16)	0.09213 (16)	0.0229 (6)
O1	0.1227 (5)	0.21648 (14)	0.24091 (14)	0.0322 (5)
O2	0.2666 (5)	0.12418 (13)	0.36775 (13)	0.0267 (5)
C1	0.5052 (6)	−0.00246 (18)	0.05424 (19)	0.0213 (6)
C2	0.3798 (7)	0.0728 (2)	0.1117 (2)	0.0227 (6)
H2	0.2878	0.1291	0.0827	0.027*
C3	0.3909 (7)	0.06454 (19)	0.2116 (2)	0.0230 (7)
C4	0.5353 (7)	−0.0181 (2)	0.2512 (2)	0.0250 (7)
H4	0.5496	−0.0255	0.3196	0.030*
C5	0.6573 (7)	−0.0889 (2)	0.1889 (2)	0.0243 (7)
H5	0.7558	−0.1452	0.2163	0.029*
C6	0.2460 (7)	0.1439 (2)	0.2732 (2)	0.0238 (7)
C7	0.1308 (7)	0.1979 (2)	0.43362 (19)	0.0268 (7)
H7A	−0.1157	0.2057	0.4167	0.032*
H7B	0.2562	0.2631	0.4290	0.032*
C8	0.1788 (8)	0.1608 (2)	0.5350 (2)	0.0322 (8)
H8A	0.0535	0.0963	0.5385	0.048*
H8B	0.0904	0.2084	0.5817	0.048*
H8C	0.4237	0.1535	0.5508	0.048*
N1'	0.6531 (6)	0.41872 (16)	0.40638 (16)	0.0225 (6)
O1'	0.1233 (5)	0.71739 (14)	0.26347 (13)	0.0307 (5)
O2'	0.2484 (5)	0.62205 (13)	0.13410 (13)	0.0257 (5)
C1'	0.5100 (6)	0.49830 (18)	0.44587 (19)	0.0210 (6)
C2'	0.3829 (7)	0.57364 (19)	0.39046 (19)	0.0214 (6)
H2'	0.2889	0.6296	0.4209	0.026*
C3'	0.3960 (7)	0.56565 (19)	0.2899 (2)	0.0213 (6)
C4'	0.5453 (7)	0.4843 (2)	0.2487 (2)	0.0231 (7)
H4'	0.5623	0.4774	0.1803	0.028*
C5'	0.6691 (7)	0.4135 (2)	0.3096 (2)	0.0241 (7)
H5'	0.7713	0.3580	0.2810	0.029*
C6'	0.2446 (7)	0.6440 (2)	0.2295 (2)	0.0219 (6)
C7'	0.0956 (8)	0.6935 (2)	0.0684 (2)	0.0325 (7)
H7'A	0.2167	0.7597	0.0789	0.039*
H7'B	−0.1497	0.6999	0.0808	0.039*
C8'	0.1316 (9)	0.6543 (2)	−0.0342 (2)	0.0401 (8)
H8'A	0.0362	0.7007	−0.0802	0.060*
H8'B	0.0070	0.5894	−0.0441	0.060*
H8'C	0.3750	0.6473	−0.0452	0.060*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N1	0.0252 (13)	0.0172 (12)	0.0269 (14)	0.0071 (10)	0.0006 (10)	0.0006 (10)
O1	0.0430 (13)	0.0242 (11)	0.0301 (12)	0.0145 (10)	−0.0005 (10)	−0.0027 (9)
O2	0.0306 (11)	0.0268 (11)	0.0235 (11)	0.0094 (9)	0.0026 (8)	−0.0026 (8)
C1	0.0165 (14)	0.0190 (15)	0.0278 (15)	0.0007 (12)	−0.0008 (12)	−0.0017 (12)
C2	0.0215 (15)	0.0172 (14)	0.0293 (17)	0.0037 (12)	−0.0014 (12)	0.0005 (12)
C3	0.0185 (15)	0.0202 (15)	0.0301 (17)	0.0034 (12)	−0.0001 (12)	−0.0015 (12)
C4	0.0248 (16)	0.0262 (16)	0.0246 (16)	0.0055 (13)	0.0021 (13)	0.0008 (13)
C5	0.0242 (15)	0.0193 (15)	0.0305 (17)	0.0093 (12)	0.0016 (12)	0.0038 (12)
C6	0.0201 (15)	0.0250 (16)	0.0258 (17)	0.0035 (13)	−0.0015 (12)	−0.0023 (13)
C7	0.0290 (16)	0.0262 (15)	0.0255 (16)	0.0089 (13)	0.0022 (12)	−0.0072 (12)
C8	0.0318 (18)	0.0359 (18)	0.0294 (18)	0.0072 (14)	0.0050 (13)	−0.0032 (14)
N1'	0.0224 (13)	0.0187 (12)	0.0264 (14)	0.0045 (10)	0.0011 (10)	−0.0022 (10)
O1'	0.0428 (13)	0.0249 (11)	0.0259 (12)	0.0169 (10)	0.0033 (9)	−0.0007 (9)
O2'	0.0327 (11)	0.0242 (11)	0.0206 (11)	0.0105 (9)	−0.0005 (8)	−0.0023 (8)
C1'	0.0195 (15)	0.0157 (15)	0.0278 (15)	0.0015 (12)	0.0021 (12)	−0.0021 (12)
C2'	0.0220 (15)	0.0157 (14)	0.0269 (17)	0.0057 (12)	0.0047 (12)	−0.0030 (12)
C3'	0.0176 (14)	0.0177 (14)	0.0282 (17)	0.0015 (12)	0.0024 (12)	−0.0046 (12)
C4'	0.0235 (15)	0.0240 (15)	0.0221 (15)	0.0053 (13)	0.0010 (12)	−0.0006 (13)
C5'	0.0228 (15)	0.0184 (14)	0.0312 (18)	0.0066 (12)	0.0033 (12)	−0.0067 (12)
C6'	0.0194 (15)	0.0208 (15)	0.0252 (17)	0.0008 (12)	0.0003 (12)	−0.0004 (12)
C7'	0.0352 (18)	0.0308 (17)	0.0319 (18)	0.0045 (14)	0.0061 (14)	−0.0019 (14)
C8'	0.044 (2)	0.047 (2)	0.0287 (19)	0.0099 (16)	0.0006 (15)	−0.0062 (15)

Geometric parameters (Å, º)

N1—C1	1.347 (3)	N1'—C1'	1.346 (3)
N1—C5	1.336 (3)	N1'—C5'	1.336 (3)
O1—C6	1.203 (3)	O1'—C6'	1.209 (3)
O2—C6	1.338 (3)	O2'—C6'	1.336 (3)
O2—C7	1.460 (3)	O2'—C7'	1.474 (3)
C1—C1^i	1.496 (5)	C1'—C1'^ii	1.496 (5)
C1—C2	1.389 (4)	C1'—C2'	1.390 (4)
C2—H2	0.9500	C2'—H2'	0.9500
C2—C3	1.382 (4)	C2'—C3'	1.388 (4)
C3—C4	1.392 (4)	C3'—C4'	1.386 (4)
C3—C6	1.494 (4)	C3'—C6'	1.496 (4)
C4—H4	0.9500	C4'—H4'	0.9500
C4—C5	1.381 (4)	C4'—C5'	1.384 (4)
C5—H5	0.9500	C5'—H5'	0.9500
C7—H7A	0.9900	C7'—H7'A	0.9900
C7—H7B	0.9900	C7'—H7'B	0.9900
C7—C8	1.507 (4)	C7'—C8'	1.505 (4)
C8—H8A	0.9800	C8'—H8'A	0.9800
C8—H8B	0.9800	C8'—H8'B	0.9800
C8—H8C	0.9800	C8'—H8'C	0.9800
C5—N1—C1	117.6 (2)	C5'—N1'—C1'	117.3 (2)
C6—O2—C7	115.9 (2)	C6'—O2'—C7'	116.5 (2)
N1—C1—C1^i	116.4 (3)	N1'—C1'—C1'^ii	116.4 (3)
N1—C1—C2	122.5 (2)	N1'—C1'—C2'	122.8 (2)
C2—C1—C1^i	121.1 (3)	C2'—C1'—C1'^ii	120.8 (3)
C1—C2—H2	120.4	C1'—C2'—H2'	120.6
C3—C2—C1	119.1 (2)	C3'—C2'—C1'	118.8 (2)
C3—C2—H2	120.4	C3'—C2'—H2'	120.6
C2—C3—C4	118.6 (2)	C2'—C3'—C6'	119.1 (2)
C2—C3—C6	119.1 (2)	C4'—C3'—C2'	118.7 (2)
C4—C3—C6	122.3 (3)	C4'—C3'—C6'	122.1 (2)
C3—C4—H4	120.7	C3'—C4'—H4'	120.8
C5—C4—C3	118.5 (3)	C5'—C4'—C3'	118.5 (3)
C5—C4—H4	120.7	C5'—C4'—H4'	120.8
N1—C5—C4	123.5 (2)	N1'—C5'—C4'	123.8 (3)
N1—C5—H5	118.2	N1'—C5'—H5'	118.1
C4—C5—H5	118.2	C4'—C5'—H5'	118.1
O1—C6—O2	124.3 (3)	O1'—C6'—O2'	123.9 (2)
O1—C6—C3	123.6 (3)	O1'—C6'—C3'	123.6 (2)
O2—C6—C3	112.1 (2)	O2'—C6'—C3'	112.4 (2)
O2—C7—H7A	110.3	O2'—C7'—H7'A	110.3
O2—C7—H7B	110.3	O2'—C7'—H7'B	110.3
O2—C7—C8	106.9 (2)	O2'—C7'—C8'	107.2 (2)
H7A—C7—H7B	108.6	H7'A—C7'—H7'B	108.5
C8—C7—H7A	110.3	C8'—C7'—H7'A	110.3
C8—C7—H7B	110.3	C8'—C7'—H7'B	110.3
C7—C8—H8A	109.5	C7'—C8'—H8'A	109.5
C7—C8—H8B	109.5	C7'—C8'—H8'B	109.5
C7—C8—H8C	109.5	C7'—C8'—H8'C	109.5
H8A—C8—H8B	109.5	H8'A—C8'—H8'B	109.5
H8A—C8—H8C	109.5	H8'A—C8'—H8'C	109.5
H8B—C8—H8C	109.5	H8'B—C8'—H8'C	109.5

Symmetry codes: (i) −x+1, −y, −z; (ii) −x+1, −y+1, −z+1.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C5—H5···O1′^iii	0.95	2.49	3.421 (3)	167
C8—H8B···O1′^iv	0.98	2.52	3.465 (3)	161
C5′—H5′···O1^v	0.95	2.47	3.404 (3)	167
C8′—H8′A···O1^vi	0.98	2.58	3.518 (3)	161
C7—H7B···N1′	0.99	2.58	3.565 (4)	172

Symmetry codes: (iii) x+1, y−1, z; (iv) −x, −y+1, −z+1; (v) x+1, y, z; (vi) −x, −y+1, −z.