A 1:1 cocrystal of sebacic acid and 4,4′-bipyridine

The crystal structure of the title compound, C₁₀H₈N₂·C₁₀H₁₈O₄, consists of sebacic acid and 4,4′-bipyridine mol­ecules. The sebacic acid mol­ecule displays an extended planar structure, but the pyridine rings of the 4,4′-bipyridine mol­ecule are twisted relative to each other, with a dihedral angle of 15.78 (7)°. The centroid-to-centroid separation of 3.6366 (11) Å indicates π–π stacking between parallel pyrid­ine rings.

Key indicators

• Single-crystal X-ray study
• T = 295 K
• Mean [sigma](C-C) = 0.002 Å
• R factor = 0.046
• wR factor = 0.132
• Data-to-parameter ratio = 17.6

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor ....       2.56
PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor ....       2.02
PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd.  #          1
              C10 H18 O4

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   3 ALERT level C = Check and explain
   0 ALERT level G = General alerts; check

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

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Computing details

Data collection: RAPID-AUTO (Rigaku, 2004); cell refinement: RAPID-AUTO; data reduction: RAPID-AUTO; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997a); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997a); molecular graphics: SHELXTL (Sheldrick, 1997b); software used to prepare material for publication: SHELXTL.

Sebacic acid–4,4'-bipyridine (1/1)

Crystal data

C10H18O4·C10H8N2	Z = 2
Mr = 358.43	F(000) = 384
Triclinic, P1	Dx = 1.304 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.9652 (18) Å	Cell parameters from 6830 reflections
b = 9.5699 (19) Å	θ = 3.2–27.5°
c = 11.700 (2) Å	µ = 0.09 mm^−1
α = 90.67 (3)°	T = 295 K
β = 95.82 (3)°	Plate, colourless
γ = 113.71 (3)°	0.45 × 0.17 × 0.09 mm
V = 912.8 (4) Å^3

Data collection

Rigaku R-AXIS RAPID IP area-detector diffractometer	2837 reflections with I > 2σ(I)
Radiation source: rotating anode	Rint = 0.040
Graphite monochromator	θmax = 27.5°, θmin = 3.1°
ω scans	h = −11→11
9086 measured reflections	k = −12→12
4146 independent reflections	l = −15→15

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)] = 0.046	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.132	H-atom parameters constrained
S = 1.01	w = 1/[σ^2(Fo^2) + (0.0708P)^2] where P = (Fo^2 + 2Fc^2)/3
4146 reflections	(Δ/σ)max = 0.002
235 parameters	Δρmax = 0.27 e Å^−3
0 restraints	Δρmin = −0.25 e Å^−3

Special details

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.

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

	x	y	z	Uiso*/Ueq
O1	−0.23605 (13)	0.40547 (13)	0.33005 (9)	0.0373 (3)
O2	0.00917 (12)	0.52801 (13)	0.27041 (9)	0.0391 (3)
H2A	0.0344	0.4734	0.3149	0.059*
O3	−1.01584 (12)	0.99001 (13)	−0.23106 (9)	0.0354 (3)
O4	−1.25312 (12)	0.87988 (13)	−0.15660 (9)	0.0340 (3)
H4B	−1.2820	0.9308	−0.2025	0.051*
N1	0.86381 (15)	0.63752 (15)	0.60884 (10)	0.0289 (3)
N2	0.39378 (14)	0.98012 (15)	0.29460 (10)	0.0273 (3)
C1	0.71598 (17)	0.61773 (17)	0.63405 (12)	0.0289 (3)
H1B	0.6740	0.5550	0.6934	0.035*
C2	0.62015 (17)	0.68425 (17)	0.57779 (12)	0.0267 (3)
H2B	0.5174	0.6670	0.5993	0.032*
C3	0.68085 (16)	0.77772 (16)	0.48813 (11)	0.0221 (3)
C4	0.83722 (17)	0.80091 (17)	0.46248 (12)	0.0270 (3)
H4A	0.8836	0.8643	0.4045	0.032*
C5	0.92300 (17)	0.72856 (18)	0.52431 (12)	0.0295 (3)
H5A	1.0269	0.7443	0.5059	0.035*
C6	0.58143 (16)	0.84878 (16)	0.42150 (11)	0.0221 (3)
C7	0.41292 (17)	0.79719 (17)	0.42667 (11)	0.0264 (3)
H7A	0.3602	0.7181	0.4731	0.032*
C8	0.32511 (17)	0.86537 (18)	0.36177 (12)	0.0285 (3)
H8A	0.2127	0.8292	0.3653	0.034*
C9	0.55369 (18)	1.02954 (18)	0.29048 (12)	0.0296 (3)
H9A	0.6031	1.1107	0.2448	0.036*
C10	0.65223 (17)	0.96742 (17)	0.35029 (12)	0.0283 (3)
H10A	0.7637	1.0045	0.3428	0.034*
C11	−0.14710 (16)	0.49952 (16)	0.27191 (11)	0.0244 (3)
C12	−0.19907 (16)	0.59802 (17)	0.19054 (12)	0.0255 (3)
H12A	−0.1816	0.5757	0.1132	0.031*
H12B	−0.1289	0.7045	0.2113	0.031*
C13	−0.37658 (16)	0.57635 (16)	0.18988 (11)	0.0242 (3)
H13A	−0.3952	0.5997	0.2667	0.029*
H13B	−0.4481	0.4704	0.1684	0.029*
C14	−0.41883 (16)	0.67963 (17)	0.10547 (12)	0.0256 (3)
H14A	−0.3471	0.7853	0.1278	0.031*
H14B	−0.3975	0.6571	0.0293	0.031*
C15	−0.59591 (16)	0.66136 (17)	0.09992 (12)	0.0251 (3)
H15A	−0.6163	0.6869	0.1756	0.030*
H15B	−0.6677	0.5551	0.0798	0.030*
C16	−0.63871 (17)	0.76071 (17)	0.01347 (12)	0.0265 (3)
H16A	−0.6179	0.7357	−0.0622	0.032*
H16B	−0.5676	0.8671	0.0338	0.032*
C17	−0.81647 (16)	0.74076 (17)	0.00814 (12)	0.0260 (3)
H17A	−0.8360	0.7688	0.0833	0.031*
H17B	−0.8872	0.6337	−0.0095	0.031*
C18	−0.86349 (17)	0.83593 (17)	−0.08112 (12)	0.0265 (3)
H18A	−0.7933	0.9433	−0.0641	0.032*
H18B	−0.8462	0.8073	−0.1569	0.032*
C19	−1.04109 (17)	0.81223 (17)	−0.08147 (12)	0.0267 (3)
H19A	−1.1097	0.7047	−0.0993	0.032*
H19B	−1.0575	0.8374	−0.0045	0.032*
C20	−1.09890 (17)	0.90456 (17)	−0.16516 (11)	0.0248 (3)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0312 (6)	0.0414 (7)	0.0447 (6)	0.0184 (5)	0.0106 (5)	0.0239 (5)
O2	0.0236 (5)	0.0474 (7)	0.0540 (7)	0.0207 (5)	0.0081 (5)	0.0301 (6)
O3	0.0309 (6)	0.0398 (7)	0.0395 (6)	0.0166 (5)	0.0094 (5)	0.0220 (5)
O4	0.0276 (6)	0.0490 (7)	0.0364 (6)	0.0251 (5)	0.0095 (5)	0.0233 (5)
N1	0.0273 (6)	0.0340 (7)	0.0302 (6)	0.0169 (6)	0.0041 (5)	0.0105 (5)
N2	0.0272 (6)	0.0338 (7)	0.0265 (6)	0.0176 (5)	0.0047 (5)	0.0094 (5)
C1	0.0269 (7)	0.0311 (8)	0.0311 (7)	0.0132 (6)	0.0063 (6)	0.0147 (6)
C2	0.0228 (7)	0.0324 (8)	0.0297 (7)	0.0149 (6)	0.0069 (6)	0.0112 (6)
C3	0.0223 (7)	0.0242 (7)	0.0224 (6)	0.0121 (6)	0.0024 (5)	0.0062 (5)
C4	0.0253 (7)	0.0338 (9)	0.0256 (7)	0.0145 (6)	0.0065 (6)	0.0112 (6)
C5	0.0229 (7)	0.0382 (9)	0.0329 (7)	0.0166 (7)	0.0077 (6)	0.0118 (6)
C6	0.0234 (7)	0.0239 (7)	0.0219 (6)	0.0124 (6)	0.0029 (5)	0.0049 (5)
C7	0.0245 (7)	0.0313 (8)	0.0272 (7)	0.0139 (6)	0.0073 (6)	0.0104 (6)
C8	0.0231 (7)	0.0374 (9)	0.0311 (7)	0.0175 (7)	0.0064 (6)	0.0108 (6)
C9	0.0286 (7)	0.0321 (9)	0.0314 (7)	0.0146 (6)	0.0070 (6)	0.0150 (6)
C10	0.0230 (7)	0.0320 (8)	0.0324 (7)	0.0126 (6)	0.0065 (6)	0.0131 (6)
C11	0.0223 (7)	0.0248 (8)	0.0272 (7)	0.0103 (6)	0.0029 (6)	0.0073 (6)
C12	0.0240 (7)	0.0279 (8)	0.0286 (7)	0.0144 (6)	0.0032 (6)	0.0097 (6)
C13	0.0235 (7)	0.0264 (8)	0.0260 (7)	0.0136 (6)	0.0023 (6)	0.0060 (6)
C14	0.0232 (7)	0.0284 (8)	0.0293 (7)	0.0139 (6)	0.0053 (6)	0.0115 (6)
C15	0.0237 (7)	0.0269 (8)	0.0283 (7)	0.0133 (6)	0.0054 (6)	0.0101 (6)
C16	0.0232 (7)	0.0283 (8)	0.0319 (7)	0.0137 (6)	0.0046 (6)	0.0114 (6)
C17	0.0210 (7)	0.0279 (8)	0.0323 (7)	0.0123 (6)	0.0061 (6)	0.0133 (6)
C18	0.0226 (7)	0.0284 (8)	0.0318 (7)	0.0128 (6)	0.0061 (6)	0.0125 (6)
C19	0.0242 (7)	0.0294 (8)	0.0303 (7)	0.0139 (6)	0.0051 (6)	0.0129 (6)
C20	0.0238 (7)	0.0274 (8)	0.0263 (7)	0.0129 (6)	0.0051 (6)	0.0073 (6)

Geometric parameters (Å, º)

O1—C11	1.2066 (17)	C10—H10A	0.9300
O2—C11	1.3173 (16)	C11—C12	1.5152 (17)
O2—H2A	0.8200	C12—C13	1.5191 (17)
O3—C20	1.2080 (17)	C12—H12A	0.9700
O4—C20	1.3203 (16)	C12—H12B	0.9700
O4—H4B	0.8200	C13—C14	1.5309 (17)
N1—C1	1.3259 (18)	C13—H13A	0.9700
N1—C5	1.3317 (19)	C13—H13B	0.9700
N2—C9	1.3231 (19)	C14—C15	1.5201 (17)
N2—C8	1.3330 (18)	C14—H14A	0.9700
C1—C2	1.3826 (18)	C14—H14B	0.9700
C1—H1B	0.9300	C15—C16	1.5203 (18)
C2—C3	1.3939 (19)	C15—H15A	0.9700
C2—H2B	0.9300	C15—H15B	0.9700
C3—C4	1.3934 (19)	C16—C17	1.5215 (17)
C3—C6	1.4911 (17)	C16—H16A	0.9700
C4—C5	1.3861 (18)	C16—H16B	0.9700
C4—H4A	0.9300	C17—C18	1.5295 (17)
C5—H5A	0.9300	C17—H17A	0.9700
C6—C10	1.3914 (19)	C17—H17B	0.9700
C6—C7	1.3961 (19)	C18—C19	1.5149 (18)
C7—C8	1.3877 (18)	C18—H18A	0.9700
C7—H7A	0.9300	C18—H18B	0.9700
C8—H8A	0.9300	C19—C20	1.5145 (17)
C9—C10	1.3893 (18)	C19—H19A	0.9700
C9—H9A	0.9300	C19—H19B	0.9700
C11—O2—H2A	109.5	C12—C13—H13A	109.4
C20—O4—H4B	109.5	C14—C13—H13A	109.4
C1—N1—C5	117.28 (11)	C12—C13—H13B	109.4
C9—N2—C8	117.41 (11)	C14—C13—H13B	109.4
N1—C1—C2	124.24 (13)	H13A—C13—H13B	108.0
N1—C1—H1B	117.9	C15—C14—C13	113.67 (11)
C2—C1—H1B	117.9	C15—C14—H14A	108.8
C1—C2—C3	118.57 (13)	C13—C14—H14A	108.8
C1—C2—H2B	120.7	C15—C14—H14B	108.8
C3—C2—H2B	120.7	C13—C14—H14B	108.8
C4—C3—C2	117.44 (12)	H14A—C14—H14B	107.7
C4—C3—C6	121.33 (12)	C14—C15—C16	113.51 (12)
C2—C3—C6	121.23 (12)	C14—C15—H15A	108.9
C5—C4—C3	119.30 (13)	C16—C15—H15A	108.9
C5—C4—H4A	120.3	C14—C15—H15B	108.9
C3—C4—H4A	120.3	C16—C15—H15B	108.9
N1—C5—C4	123.15 (13)	H15A—C15—H15B	107.7
N1—C5—H5A	118.4	C15—C16—C17	113.05 (12)
C4—C5—H5A	118.4	C15—C16—H16A	109.0
C10—C6—C7	117.31 (12)	C17—C16—H16A	109.0
C10—C6—C3	121.40 (12)	C15—C16—H16B	109.0
C7—C6—C3	121.28 (12)	C17—C16—H16B	109.0
C8—C7—C6	119.20 (13)	H16A—C16—H16B	107.8
C8—C7—H7A	120.4	C16—C17—C18	113.86 (11)
C6—C7—H7A	120.4	C16—C17—H17A	108.8
N2—C8—C7	123.28 (13)	C18—C17—H17A	108.8
N2—C8—H8A	118.4	C16—C17—H17B	108.8
C7—C8—H8A	118.4	C18—C17—H17B	108.8
N2—C9—C10	123.88 (13)	H17A—C17—H17B	107.7
N2—C9—H9A	118.1	C19—C18—C17	111.31 (12)
C10—C9—H9A	118.1	C19—C18—H18A	109.4
C9—C10—C6	118.90 (13)	C17—C18—H18A	109.4
C9—C10—H10A	120.5	C19—C18—H18B	109.4
C6—C10—H10A	120.5	C17—C18—H18B	109.4
O1—C11—O2	123.63 (12)	H18A—C18—H18B	108.0
O1—C11—C12	125.17 (12)	C20—C19—C18	115.46 (12)
O2—C11—C12	111.19 (12)	C20—C19—H19A	108.4
C11—C12—C13	114.69 (11)	C18—C19—H19A	108.4
C11—C12—H12A	108.6	C20—C19—H19B	108.4
C13—C12—H12A	108.6	C18—C19—H19B	108.4
C11—C12—H12B	108.6	H19A—C19—H19B	107.5
C13—C12—H12B	108.6	O3—C20—O4	124.06 (12)
H12A—C12—H12B	107.6	O3—C20—C19	124.95 (12)
C12—C13—C14	111.29 (11)	O4—C20—C19	110.98 (12)
C5—N1—C1—C2	0.5 (2)	C8—N2—C9—C10	1.0 (2)
N1—C1—C2—C3	0.4 (2)	N2—C9—C10—C6	−1.8 (2)
C1—C2—C3—C4	−1.4 (2)	C7—C6—C10—C9	1.2 (2)
C1—C2—C3—C6	177.99 (13)	C3—C6—C10—C9	−179.84 (13)
C2—C3—C4—C5	1.4 (2)	O1—C11—C12—C13	2.8 (2)
C6—C3—C4—C5	−177.93 (13)	O2—C11—C12—C13	−178.02 (12)
C1—N1—C5—C4	−0.5 (2)	C11—C12—C13—C14	−179.91 (12)
C3—C4—C5—N1	−0.5 (2)	C12—C13—C14—C15	179.23 (12)
C4—C3—C6—C10	−15.1 (2)	C13—C14—C15—C16	−178.32 (12)
C2—C3—C6—C10	165.51 (14)	C14—C15—C16—C17	179.65 (12)
C4—C3—C6—C7	163.82 (14)	C15—C16—C17—C18	−178.14 (12)
C2—C3—C6—C7	−15.5 (2)	C16—C17—C18—C19	−179.48 (12)
C10—C6—C7—C8	0.0 (2)	C17—C18—C19—C20	178.61 (12)
C3—C6—C7—C8	−179.03 (13)	C18—C19—C20—O3	1.8 (2)
C9—N2—C8—C7	0.2 (2)	C18—C19—C20—O4	−178.02 (12)
C6—C7—C8—N2	−0.7 (2)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2A···N1^i	0.82	1.84	2.6418 (15)	165
O4—H4B···N2^ii	0.82	1.84	2.6436 (15)	167
C2—H2B···O1^iii	0.93	2.56	3.486 (2)	174
C4—H4A···O3^iv	0.93	2.59	3.511 (2)	173

Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) −x−1, −y+2, −z; (iii) −x, −y+1, −z+1; (iv) −x, −y+2, −z.