4,4′-Bipyridine–2-nitro­benzonic acid (1/2)

The title compound, C₁₀H₈N₂·2C₇H₅NO₄, was obtained as a by-product of the hydro­thermal reaction of ZnSO₄ with 2-nitro­benzoic acid and 4,4′-bipyridine. The 4,4′-bipyridine molecule lies on an inversion centre. There are O—H...N and C—H...O hydrogen bonds between the components in the crystal structure.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.004 Å
• R factor = 0.074
• wR factor = 0.156
• Data-to-parameter ratio = 15.6

checkCIF/PLATON results

No syntax errors found



Alert level A
DIFF020_ALERT_1_A  _diffrn_standards_interval_count and
            _diffrn_standards_interval_time are missing. Number of measurements
            between standards or time (min) between standards.

Alert level C
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ ....          ?
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical .          ?
PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given .......          ?
PLAT199_ALERT_1_C Check the Reported _cell_measurement_temperature        293 K
PLAT200_ALERT_1_C Check the Reported _diffrn_ambient_temperature .        293 K
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for         C3
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for         N2
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C12
PLAT355_ALERT_3_C Long    O-H Bond (0.82A)   O4     -   H11    ...       1.02 Ang.

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

   5 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
   1 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: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1994); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Siemens, 1994); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

4,4'-Bipyridine–2-nitrobenzonic acid (1/2)

Crystal data

C10H8N2·2C7H5NO4	F(000) = 508
Mr = 490.42	Dx = 1.439 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 7.0788 (13) Å	Cell parameters from 1782 reflections
b = 18.660 (3) Å	θ = 3.1–27.5°
c = 8.6256 (16) Å	µ = 0.11 mm^−1
β = 96.649 (9)°	T = 293 K
V = 1131.7 (3) Å^3	Prism, orange
Z = 2	0.55 × 0.20 × 0.06 mm

Data collection

Bruker P4 diffractometer	2600 independent reflections
Radiation source: fine-focus sealed tube	2018 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.031
ω scans	θmax = 27.5°, θmin = 3.1°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −9→6
Tmin = 0.974, Tmax = 0.993	k = −24→22
8485 measured reflections	l = −11→10

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)] = 0.074	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.156	H atoms treated by a mixture of independent and constrained refinement
S = 1.19	w = 1/[σ^2(Fo^2) + (0.0523P)^2 + 0.3073P] where P = (Fo^2 + 2Fc^2)/3
2590 reflections	(Δ/σ)max < 0.001
166 parameters	Δρmax = 0.12 e Å^−3
0 restraints	Δρmin = −0.16 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
C1	0.1451 (4)	0.52894 (15)	0.7710 (3)	0.0675 (7)
H1A	0.0906	0.5183	0.6703	0.081*
C2	0.3193 (4)	0.50005 (14)	0.8215 (3)	0.0635 (7)
H2A	0.3799	0.4707	0.7555	0.076*
C3	0.4049 (3)	0.51444 (11)	0.9702 (2)	0.0451 (5)
C4	0.3039 (4)	0.55782 (14)	1.0604 (3)	0.0636 (7)
H4A	0.3539	0.5688	1.1621	0.076*
C5	0.1301 (4)	0.58503 (15)	1.0015 (3)	0.0636 (7)
H5A	0.0659	0.6144	1.0650	0.076*
C6	0.4546 (3)	0.27031 (12)	0.5085 (3)	0.0483 (5)
C7	0.5984 (4)	0.23109 (14)	0.5907 (3)	0.0606 (7)
H7A	0.5821	0.1825	0.6094	0.073*
C8	0.7651 (4)	0.26463 (16)	0.6442 (3)	0.0678 (7)
H8A	0.8627	0.2390	0.7006	0.081*
C9	0.7883 (4)	0.33642 (16)	0.6146 (3)	0.0664 (7)
H9A	0.9036	0.3586	0.6474	0.080*
C10	0.6416 (3)	0.37573 (14)	0.5366 (3)	0.0587 (6)
H10A	0.6577	0.4245	0.5207	0.070*
C11	0.4703 (3)	0.34320 (12)	0.4814 (2)	0.0468 (5)
C12	0.3170 (3)	0.38830 (13)	0.3956 (3)	0.0538 (6)
O1	0.1286 (3)	0.26101 (13)	0.4685 (3)	0.0950 (7)
O2	0.2905 (3)	0.17322 (11)	0.3962 (3)	0.0934 (7)
O3	0.2625 (3)	0.44273 (10)	0.4514 (3)	0.0909 (7)
O4	0.2563 (3)	0.36450 (10)	0.2583 (2)	0.0703 (6)
H11	0.145 (4)	0.3937 (16)	0.206 (3)	0.084*
N1	0.0501 (3)	0.57122 (10)	0.8581 (2)	0.0544 (5)
N2	0.2781 (3)	0.23221 (12)	0.4533 (3)	0.0615 (6)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0648 (17)	0.0806 (18)	0.0530 (14)	0.0221 (14)	−0.0103 (12)	−0.0067 (13)
C2	0.0597 (16)	0.0760 (17)	0.0524 (13)	0.0228 (13)	−0.0033 (12)	−0.0108 (12)
C3	0.0461 (12)	0.0421 (11)	0.0469 (11)	0.0056 (9)	0.0042 (10)	0.0044 (9)
C4	0.0566 (16)	0.0812 (18)	0.0501 (13)	0.0204 (13)	−0.0059 (12)	−0.0092 (12)
C5	0.0569 (16)	0.0734 (17)	0.0592 (15)	0.0192 (12)	0.0017 (12)	−0.0079 (12)
C6	0.0410 (12)	0.0545 (13)	0.0494 (12)	0.0027 (10)	0.0057 (10)	−0.0019 (10)
C7	0.0561 (15)	0.0604 (15)	0.0649 (15)	0.0110 (12)	0.0051 (12)	0.0063 (12)
C8	0.0515 (15)	0.0822 (19)	0.0664 (16)	0.0208 (14)	−0.0073 (13)	−0.0032 (14)
C9	0.0467 (14)	0.0817 (19)	0.0679 (16)	0.0020 (13)	−0.0061 (13)	−0.0193 (14)
C10	0.0563 (15)	0.0577 (14)	0.0601 (14)	−0.0008 (11)	−0.0018 (12)	−0.0128 (11)
C11	0.0443 (12)	0.0525 (13)	0.0430 (11)	0.0072 (10)	0.0027 (10)	−0.0080 (9)
C12	0.0531 (14)	0.0513 (13)	0.0552 (13)	0.0093 (11)	−0.0010 (11)	−0.0070 (11)
O1	0.0440 (11)	0.1032 (17)	0.138 (2)	0.0008 (11)	0.0132 (12)	−0.0082 (14)
O2	0.0849 (16)	0.0674 (13)	0.1252 (19)	−0.0128 (11)	0.0006 (13)	−0.0234 (12)
O3	0.0962 (16)	0.0708 (12)	0.0969 (15)	0.0381 (11)	−0.0264 (12)	−0.0338 (11)
O4	0.0698 (12)	0.0799 (12)	0.0562 (10)	0.0322 (10)	−0.0138 (9)	−0.0140 (9)
N1	0.0505 (12)	0.0540 (11)	0.0570 (11)	0.0109 (9)	−0.0006 (9)	0.0049 (9)
N2	0.0489 (13)	0.0658 (14)	0.0696 (13)	−0.0042 (10)	0.0054 (10)	0.0039 (11)

Geometric parameters (Å, º)

C1—N1	1.325 (3)	C7—C8	1.368 (4)
C1—C2	1.370 (3)	C7—H7A	0.9300
C1—H1A	0.9300	C8—C9	1.377 (4)
C2—C3	1.380 (3)	C8—H8A	0.9300
C2—H2A	0.9300	C9—C10	1.381 (4)
C3—C4	1.379 (3)	C9—H9A	0.9300
C3—C3^i	1.486 (4)	C10—C11	1.390 (3)
C4—C5	1.372 (3)	C10—H10A	0.9300
C4—H4A	0.9300	C11—C12	1.500 (3)
C5—N1	1.325 (3)	C12—O3	1.206 (3)
C5—H5A	0.9300	C12—O4	1.291 (3)
C6—C7	1.381 (3)	O1—N2	1.207 (3)
C6—C11	1.387 (3)	O2—N2	1.213 (3)
C6—N2	1.468 (3)	O4—H11	1.02 (3)
N1—C1—C2	123.5 (2)	C7—C8—C9	119.9 (2)
N1—C1—H1A	118.3	C7—C8—H8A	120.0
C2—C1—H1A	118.3	C9—C8—H8A	120.0
C1—C2—C3	120.1 (2)	C8—C9—C10	120.5 (2)
C1—C2—H2A	120.0	C8—C9—H9A	119.7
C3—C2—H2A	120.0	C10—C9—H9A	119.7
C4—C3—C2	116.0 (2)	C9—C10—C11	120.8 (2)
C4—C3—C3^i	121.7 (2)	C9—C10—H10A	119.6
C2—C3—C3^i	122.3 (2)	C11—C10—H10A	119.6
C5—C4—C3	120.6 (2)	C6—C11—C10	117.0 (2)
C5—C4—H4A	119.7	C6—C11—C12	124.5 (2)
C3—C4—H4A	119.7	C10—C11—C12	118.5 (2)
N1—C5—C4	122.8 (2)	O3—C12—O4	124.6 (2)
N1—C5—H5A	118.6	O3—C12—C11	121.5 (2)
C4—C5—H5A	118.6	O4—C12—C11	113.86 (19)
C7—C6—C11	122.5 (2)	C12—O4—H11	112.4 (16)
C7—C6—N2	117.3 (2)	C1—N1—C5	117.1 (2)
C11—C6—N2	120.1 (2)	O1—N2—O2	123.6 (2)
C8—C7—C6	119.1 (2)	O1—N2—C6	118.2 (2)
C8—C7—H7A	120.4	O2—N2—C6	118.2 (2)
C6—C7—H7A	120.4
N1—C1—C2—C3	0.1 (5)	N2—C6—C11—C12	−0.6 (3)
C1—C2—C3—C4	0.7 (4)	C9—C10—C11—C6	0.0 (3)
C1—C2—C3—C3^i	−178.9 (3)	C9—C10—C11—C12	−179.2 (2)
C2—C3—C4—C5	−0.9 (4)	C6—C11—C12—O3	127.4 (3)
C3^i—C3—C4—C5	178.6 (3)	C10—C11—C12—O3	−53.4 (4)
C3—C4—C5—N1	0.5 (4)	C6—C11—C12—O4	−54.6 (3)
C11—C6—C7—C8	−1.8 (4)	C10—C11—C12—O4	124.5 (2)
N2—C6—C7—C8	180.0 (2)	C2—C1—N1—C5	−0.6 (4)
C6—C7—C8—C9	−0.6 (4)	C4—C5—N1—C1	0.3 (4)
C7—C8—C9—C10	2.6 (4)	C7—C6—N2—O1	136.3 (3)
C8—C9—C10—C11	−2.3 (4)	C11—C6—N2—O1	−41.9 (3)
C7—C6—C11—C10	2.1 (3)	C7—C6—N2—O2	−43.0 (3)
N2—C6—C11—C10	−179.8 (2)	C11—C6—N2—O2	138.8 (2)
C7—C6—C11—C12	−178.8 (2)

Symmetry code: (i) −x+1, −y+1, −z+2.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O4—H11···N1^ii	1.02 (3)	1.57 (3)	2.578 (2)	169 (3)
C10—H10A···O3^iii	0.93	2.55	3.454 (3)	166

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