trans-1,2-Bis(4-pyrid­yl)ethyl­ene monohydrate

In the title compound, C₁₂H₁₀N₂·H₂O, inter­molecular O—H...N hydrogen bonds are highly effective in forming a one-dimensional chain. In addition, the presence of C—H...O hydrogen bonds helps to build a three-dimensional supramolecular network, thereby stabilizing the crystal structure.

Key indicators

• Single-crystal X-ray study
• T = 100 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.036
• wR factor = 0.090
• Data-to-parameter ratio = 8.3

checkCIF/PLATON results

No syntax errors found



Alert level G
REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is
            correct. If it is not, please give the correct count in the
            _publ_section_exptl_refinement section of the submitted CIF.
           From the CIF: _diffrn_reflns_theta_max           26.99
           From the CIF: _reflns_number_total               1194
           Count of symmetry unique reflns         1216
           Completeness (_total/calc)             98.19%
           TEST3: Check Friedels for noncentro structure
           Estimate of Friedel pairs measured         0
           Fraction of Friedel pairs measured     0.000
           Are heavy atom types Z>Si present         no

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

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   0 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: CrystalClear (Molecular Structure Corporation & Rigaku Corporation, 2001); cell refinement: CrystalClear; data reduction: TEXSAN (Molecular Structure Corporation & Rigaku Corporation, 2000); program(s) used to solve structure: SHELXTL (Bruker, 2000); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

'Trans-1,2-bis(4-pyridyl)ethylene monohydrate'

Crystal data

C12H10N2·H2O	F(000) = 424
Mr = 200.24	Dx = 1.289 Mg m^−3
Orthorhombic, Pna21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2n	Cell parameters from 4671 reflections
a = 9.1778 (18) Å	θ = 3.5–27.5°
b = 14.768 (3) Å	µ = 0.08 mm^−1
c = 7.6109 (15) Å	T = 100 K
V = 1031.5 (4) Å^3	Block, colorless
Z = 4	0.30 × 0.20 × 0.20 mm

Data collection

Rigaku Mercury CCD area-detector diffractometer	1194 independent reflections
Radiation source: Rigaku rotating anode	1182 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.072
Detector resolution: 14.6199 pixels mm^-1	θmax = 27.0°, θmin = 4.7°
φ and ω scans	h = −11→11
Absorption correction: multi-scan (REQAB; Jacobson, 1998)	k = −18→15
Tmin = 0.978, Tmax = 0.982	l = −9→9
9337 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)] = 0.036	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.090	H atoms treated by a mixture of independent and constrained refinement
S = 1.17	w = 1/[σ^2(Fo^2) + (0.0372P)^2 + 0.2772P] where P = (Fo^2 + 2Fc^2)/3
1194 reflections	(Δ/σ)max < 0.001
144 parameters	Δρmax = 0.20 e Å^−3
1 restraint	Δρmin = −0.15 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	0.1828 (2)	0.61196 (13)	0.2070 (3)	0.0212 (4)
H1	0.2535	0.5861	0.2831	0.025*
C2	0.1745 (2)	0.70569 (12)	0.1979 (3)	0.0194 (4)
H2	0.2383	0.7424	0.2655	0.023*
C3	0.07055 (19)	0.74514 (12)	0.0875 (2)	0.0169 (4)
C4	−0.0196 (2)	0.68695 (13)	−0.0068 (3)	0.0200 (4)
H4	−0.0925	0.7106	−0.0825	0.024*
C5	−0.0019 (2)	0.59407 (13)	0.0110 (3)	0.0216 (4)
H5	−0.0642	0.5555	−0.0550	0.026*
C6	0.0527 (2)	0.84432 (13)	0.0676 (3)	0.0186 (4)
H6	−0.0232	0.8656	−0.0066	0.022*
C7	0.13643 (19)	0.90556 (12)	0.1473 (3)	0.0177 (4)
H7	0.2130	0.8836	0.2197	0.021*
C8	0.1199 (2)	1.00455 (12)	0.1325 (3)	0.0174 (4)
C9	−0.0053 (2)	1.04779 (13)	0.0708 (3)	0.0209 (4)
H9	−0.0877	1.0134	0.0356	0.025*
C10	−0.0078 (2)	1.14180 (14)	0.0616 (3)	0.0239 (5)
H10	−0.0941	1.1703	0.0202	0.029*
C11	0.2240 (2)	1.15229 (13)	0.1681 (3)	0.0234 (4)
H11	0.3050	1.1884	0.2016	0.028*
C12	0.2359 (2)	1.05955 (13)	0.1844 (3)	0.0202 (4)
H12	0.3223	1.0333	0.2306	0.024*
H1A	0.118 (4)	0.421 (3)	0.037 (6)	0.064 (11)*
H1B	0.109 (4)	0.327 (3)	0.032 (6)	0.081 (13)*
N1	0.09747 (18)	0.55563 (10)	0.1153 (2)	0.0224 (4)
N2	0.1049 (2)	1.19441 (11)	0.1080 (2)	0.0246 (4)
O1	0.1330 (2)	0.37520 (11)	−0.0280 (2)	0.0323 (4)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0228 (9)	0.0184 (9)	0.0223 (10)	0.0033 (7)	0.0036 (9)	0.0025 (8)
C2	0.0202 (9)	0.0169 (9)	0.0211 (10)	−0.0004 (7)	0.0022 (8)	−0.0008 (8)
C3	0.0192 (8)	0.0135 (8)	0.0182 (9)	0.0002 (6)	0.0053 (8)	0.0006 (7)
C4	0.0217 (9)	0.0169 (9)	0.0215 (9)	−0.0003 (7)	0.0014 (8)	0.0002 (8)
C5	0.0251 (10)	0.0155 (9)	0.0242 (11)	−0.0036 (7)	0.0050 (8)	−0.0040 (8)
C6	0.0204 (9)	0.0159 (9)	0.0196 (9)	0.0006 (7)	−0.0001 (8)	0.0005 (7)
C7	0.0179 (8)	0.0153 (9)	0.0200 (10)	0.0015 (6)	0.0009 (7)	0.0019 (7)
C8	0.0251 (9)	0.0138 (8)	0.0134 (9)	0.0003 (7)	0.0028 (7)	0.0001 (7)
C9	0.0249 (9)	0.0173 (9)	0.0205 (9)	−0.0018 (7)	−0.0013 (8)	−0.0016 (8)
C10	0.0322 (10)	0.0179 (9)	0.0216 (10)	0.0060 (8)	−0.0025 (9)	−0.0009 (8)
C11	0.0324 (11)	0.0173 (8)	0.0205 (10)	−0.0054 (8)	0.0007 (9)	−0.0032 (7)
C12	0.0226 (9)	0.0201 (9)	0.0178 (9)	0.0004 (7)	−0.0014 (8)	−0.0008 (8)
N1	0.0293 (8)	0.0133 (7)	0.0246 (9)	0.0016 (6)	0.0069 (8)	0.0018 (7)
N2	0.0382 (9)	0.0144 (7)	0.0211 (9)	0.0003 (7)	−0.0010 (8)	−0.0009 (7)
O1	0.0483 (10)	0.0170 (8)	0.0314 (9)	−0.0002 (7)	0.0124 (8)	0.0006 (7)

Geometric parameters (Å, º)

C1—N1	1.339 (3)	C7—H7	0.9500
C1—C2	1.388 (3)	C8—C12	1.396 (3)
C1—H1	0.9500	C8—C9	1.396 (3)
C2—C3	1.399 (3)	C9—C10	1.390 (3)
C2—H2	0.9500	C9—H9	0.9500
C3—C4	1.392 (3)	C10—N2	1.341 (3)
C3—C6	1.482 (2)	C10—H10	0.9500
C4—C5	1.388 (3)	C11—N2	1.338 (3)
C4—H4	0.9500	C11—C12	1.379 (3)
C5—N1	1.336 (3)	C11—H11	0.9500
C5—H5	0.9500	C12—H12	0.9500
C6—C7	1.333 (3)	O1—H1A	0.85 (4)
C6—H6	0.9500	O1—H1B	0.87 (5)
C7—C8	1.474 (2)
N1—C1—C2	124.18 (18)	C8—C7—H7	117.3
N1—C1—H1	117.9	C12—C8—C9	117.16 (17)
C2—C1—H1	117.9	C12—C8—C7	118.50 (17)
C1—C2—C3	118.87 (18)	C9—C8—C7	124.34 (17)
C1—C2—H2	120.6	C10—C9—C8	119.19 (18)
C3—C2—H2	120.6	C10—C9—H9	120.4
C4—C3—C2	117.25 (17)	C8—C9—H9	120.4
C4—C3—C6	119.47 (17)	N2—C10—C9	123.51 (19)
C2—C3—C6	123.28 (16)	N2—C10—H10	118.2
C5—C4—C3	119.38 (18)	C9—C10—H10	118.2
C5—C4—H4	120.3	N2—C11—C12	123.85 (19)
C3—C4—H4	120.3	N2—C11—H11	118.1
N1—C5—C4	123.89 (18)	C12—C11—H11	118.1
N1—C5—H5	118.1	C11—C12—C8	119.47 (18)
C4—C5—H5	118.1	C11—C12—H12	120.3
C7—C6—C3	124.08 (17)	C8—C12—H12	120.3
C7—C6—H6	118.0	C5—N1—C1	116.43 (16)
C3—C6—H6	118.0	C11—N2—C10	116.79 (17)
C6—C7—C8	125.35 (17)	H1A—O1—H1B	108 (4)
C6—C7—H7	117.3
N1—C1—C2—C3	0.4 (3)	C12—C8—C9—C10	1.0 (3)
C1—C2—C3—C4	0.3 (3)	C7—C8—C9—C10	−179.58 (19)
C1—C2—C3—C6	−179.84 (18)	C8—C9—C10—N2	0.5 (3)
C2—C3—C4—C5	−0.7 (3)	N2—C11—C12—C8	1.5 (3)
C6—C3—C4—C5	179.49 (18)	C9—C8—C12—C11	−1.9 (3)
C3—C4—C5—N1	0.4 (3)	C7—C8—C12—C11	178.63 (18)
C4—C3—C6—C7	−177.7 (2)	C4—C5—N1—C1	0.3 (3)
C2—C3—C6—C7	2.5 (3)	C2—C1—N1—C5	−0.7 (3)
C3—C6—C7—C8	−178.96 (19)	C12—C11—N2—C10	0.0 (3)
C6—C7—C8—C12	−163.5 (2)	C9—C10—N2—C11	−1.0 (3)
C6—C7—C8—C9	17.1 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C7—H7···O1^i	0.95	2.39	3.284 (3)	157
O1—H1B···N2^ii	0.87 (5)	2.05 (5)	2.875 (2)	159 (4)
O1—H1A···N1	0.85 (4)	2.08 (4)	2.897 (2)	161 (4)

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