organic compounds
2,6-Bis(3-phenyl-1H-pyrazol-5-yl)pyridine monohydrate
aDepartment of Chemistry, University of Science and Technology of China, Hefei, Anhui 230026, People's Republic of China
*Correspondence e-mail: jianyud@mail.ustc.edu.cn
In the title compound, C23H17N5·H2O, the pyrazole rings are slightly twisted from the central pyridine ring, forming dihedral angles of 5.3 (2) and 3.5 (2)°. The pyrazole and phenyl rings on each side of the pyridine ring are also approximately coplanar, making dihedral angles of 6.0 (2) and 4.5 (2)°. In the 2,6-bis(3-phenyl-1H-pyrazol-5-yl)pyridine and water molecules are linked together via N—H⋯O and O—H⋯N hydrogen bonds, forming a column running parallel to the a axis.
Related literature
For general background, see: Dias & Gamage (2007); Zhou & Chen (2007a,b); Zhang et al. (2007).
Experimental
Crystal data
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Refinement
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Data collection: SMART (Bruker, 2001); cell SAINT (Bruker, 2001); 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 publCIF (Westrip, 2008).
Supporting information
10.1107/S1600536808008520/is2276sup1.cif
contains datablocks global, I. DOI:Structure factors: contains datablock I. DOI: 10.1107/S1600536808008520/is2276Isup2.hkl
All reagents were of analytical grade and used without further purification. Bppp was prepared by the general procedure of Zhou and Chen (2007a). Bppp (36 mg, 0.1 mmol) in 20 ml of water in a sealed stainless vial was heated at 170 °C for 48 h. Cooling the vial slowly (1 °C/h) afforded colorless crystals. Analysis found: C 72.64, H 4.90, N 18.25%; calculated for C23H19N5O: C 72.42, H 5.02, N 18.36%.
Water H atoms were located in a difference Fourier map and refined isotropically with bond and distance restraints of O—H = 0.83 (1) and H···H = 1.45 (1) Å. Other H atoms were positioned geometrically and treated as riding, with C—H = 0.93 and N—H = 0.86 Å, and with Uiso(H) = 1.2Ueq(C,N).
Data collection: SMART (Bruker, 2001); cell
SAINT (Bruker, 2001); data reduction: SAINT (Bruker, 2001); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008) and publCIF (Westrip, 2008).C23H17N5·H2O | F(000) = 800 |
Mr = 381.43 | Dx = 1.277 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2yn | Cell parameters from 1722 reflections |
a = 8.0581 (17) Å | θ = 2.8–22.2° |
b = 19.975 (2) Å | µ = 0.08 mm−1 |
c = 12.451 (2) Å | T = 298 K |
β = 98.273 (3)° | Needle, colorless |
V = 1983.2 (6) Å3 | 0.42 × 0.11 × 0.07 mm |
Z = 4 |
Bruker SMART CCD area-detector diffractometer | 3513 independent reflections |
Radiation source: fine-focus sealed tube | 1796 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.077 |
ϕ and ω scans | θmax = 25.1°, θmin = 1.9° |
Absorption correction: multi-scan (SADABS; Sheldrick, 2002) | h = −8→9 |
Tmin = 0.966, Tmax = 0.994 | k = −22→23 |
9869 measured reflections | l = −14→13 |
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.063 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.159 | w = 1/[σ2(Fo2) + (0.0411P)2] where P = (Fo2 + 2Fc2)/3 |
S = 1.05 | (Δ/σ)max < 0.001 |
3513 reflections | Δρmax = 0.18 e Å−3 |
271 parameters | Δρmin = −0.18 e Å−3 |
3 restraints | Extinction correction: SHELXTL (Sheldrick, 2008), Fc^*^=kFc[1+0.001xFc^2^λ^3^/sin(2θ)]^-1/4^ |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.0038 (10) |
C23H17N5·H2O | V = 1983.2 (6) Å3 |
Mr = 381.43 | Z = 4 |
Monoclinic, P21/n | Mo Kα radiation |
a = 8.0581 (17) Å | µ = 0.08 mm−1 |
b = 19.975 (2) Å | T = 298 K |
c = 12.451 (2) Å | 0.42 × 0.11 × 0.07 mm |
β = 98.273 (3)° |
Bruker SMART CCD area-detector diffractometer | 3513 independent reflections |
Absorption correction: multi-scan (SADABS; Sheldrick, 2002) | 1796 reflections with I > 2σ(I) |
Tmin = 0.966, Tmax = 0.994 | Rint = 0.077 |
9869 measured reflections |
R[F2 > 2σ(F2)] = 0.063 | 3 restraints |
wR(F2) = 0.159 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.05 | Δρmax = 0.18 e Å−3 |
3513 reflections | Δρmin = −0.18 e Å−3 |
271 parameters |
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 F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > σ(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ 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 | ||
N1 | 0.1701 (3) | 0.11239 (13) | 0.7473 (2) | 0.0464 (7) | |
N2 | 0.4662 (3) | 0.11019 (14) | 0.8827 (2) | 0.0509 (7) | |
H17 | 0.3906 | 0.0825 | 0.8969 | 0.061* | |
N3 | 0.6177 (3) | 0.11540 (14) | 0.9425 (2) | 0.0510 (7) | |
N4 | −0.0667 (3) | 0.02481 (13) | 0.7985 (2) | 0.0489 (7) | |
H5 | 0.0272 | 0.0252 | 0.8413 | 0.059* | |
N5 | −0.1970 (3) | −0.01481 (14) | 0.8133 (2) | 0.0535 (8) | |
C1 | 0.0274 (4) | 0.10897 (16) | 0.6795 (3) | 0.0469 (8) | |
C2 | −0.0007 (5) | 0.14642 (18) | 0.5851 (3) | 0.0671 (11) | |
H2 | −0.1022 | 0.1436 | 0.5392 | 0.081* | |
C3 | 0.1241 (5) | 0.1876 (2) | 0.5611 (3) | 0.0800 (13) | |
H3 | 0.1081 | 0.2132 | 0.4981 | 0.096* | |
C4 | 0.2718 (5) | 0.19125 (18) | 0.6292 (3) | 0.0705 (11) | |
H4 | 0.3580 | 0.2188 | 0.6134 | 0.085* | |
C5 | 0.2900 (4) | 0.15272 (16) | 0.7226 (3) | 0.0485 (9) | |
C6 | 0.4445 (4) | 0.15273 (16) | 0.7981 (3) | 0.0464 (8) | |
C7 | 0.5920 (4) | 0.18745 (16) | 0.8030 (3) | 0.0491 (9) | |
H7 | 0.6173 | 0.2208 | 0.7558 | 0.059* | |
C8 | 0.6966 (4) | 0.16260 (15) | 0.8935 (3) | 0.0459 (8) | |
C9 | 0.8667 (4) | 0.18274 (17) | 0.9361 (3) | 0.0479 (9) | |
C10 | 0.9428 (5) | 0.2353 (2) | 0.8903 (3) | 0.0759 (12) | |
H10 | 0.8857 | 0.2576 | 0.8306 | 0.091* | |
C11 | 1.1031 (6) | 0.2547 (2) | 0.9324 (4) | 0.0936 (15) | |
H11 | 1.1533 | 0.2903 | 0.9013 | 0.112* | |
C12 | 1.1886 (5) | 0.2221 (2) | 1.0195 (4) | 0.0860 (14) | |
H12 | 1.2972 | 0.2350 | 1.0472 | 0.103* | |
C13 | 1.1139 (5) | 0.17056 (19) | 1.0656 (4) | 0.0744 (12) | |
H13 | 1.1704 | 0.1492 | 1.1265 | 0.089* | |
C14 | 0.9565 (4) | 0.15005 (17) | 1.0232 (3) | 0.0607 (10) | |
H14 | 0.9091 | 0.1134 | 1.0535 | 0.073* | |
C15 | −0.0992 (4) | 0.06365 (16) | 0.7095 (2) | 0.0454 (8) | |
C16 | −0.2579 (4) | 0.04886 (16) | 0.6641 (3) | 0.0506 (9) | |
H16 | −0.3166 | 0.0673 | 0.6013 | 0.061* | |
C17 | −0.3159 (4) | 0.00052 (17) | 0.7303 (3) | 0.0474 (8) | |
C18 | −0.4788 (4) | −0.03241 (18) | 0.7192 (3) | 0.0510 (9) | |
C19 | −0.6077 (4) | −0.01190 (19) | 0.6401 (3) | 0.0617 (10) | |
H19 | −0.5885 | 0.0225 | 0.5930 | 0.074* | |
C20 | −0.7635 (5) | −0.0415 (2) | 0.6298 (3) | 0.0717 (12) | |
H20 | −0.8480 | −0.0271 | 0.5759 | 0.086* | |
C21 | −0.7945 (5) | −0.0916 (2) | 0.6984 (4) | 0.0772 (13) | |
H21 | −0.9002 | −0.1112 | 0.6919 | 0.093* | |
C22 | −0.6695 (5) | −0.1130 (2) | 0.7767 (3) | 0.0756 (12) | |
H22A | −0.6894 | −0.1480 | 0.8225 | 0.091* | |
C23 | −0.5147 (5) | −0.0831 (2) | 0.7880 (3) | 0.0668 (11) | |
H23A | −0.4319 | −0.0973 | 0.8432 | 0.080* | |
O1 | 0.2448 (3) | 0.01202 (14) | 0.9621 (2) | 0.0566 (7) | |
H22 | 0.216 (6) | 0.028 (2) | 1.019 (2) | 0.15 (2)* | |
H23 | 0.298 (6) | −0.0242 (14) | 0.967 (3) | 0.15 (2)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
N1 | 0.0427 (17) | 0.0464 (17) | 0.0497 (16) | 0.0026 (14) | 0.0054 (14) | −0.0008 (13) |
N2 | 0.0401 (18) | 0.0554 (18) | 0.0563 (17) | −0.0080 (14) | 0.0035 (14) | 0.0059 (15) |
N3 | 0.0378 (17) | 0.0568 (18) | 0.0577 (17) | −0.0084 (14) | 0.0040 (14) | 0.0026 (14) |
N4 | 0.0354 (17) | 0.0575 (18) | 0.0516 (17) | −0.0011 (14) | −0.0011 (13) | 0.0039 (14) |
N5 | 0.0397 (17) | 0.0625 (19) | 0.0577 (18) | −0.0063 (15) | 0.0048 (15) | 0.0025 (15) |
C1 | 0.050 (2) | 0.041 (2) | 0.049 (2) | 0.0068 (17) | 0.0032 (18) | −0.0019 (16) |
C2 | 0.063 (3) | 0.059 (2) | 0.071 (3) | −0.005 (2) | −0.017 (2) | 0.020 (2) |
C3 | 0.084 (3) | 0.076 (3) | 0.074 (3) | −0.014 (3) | −0.011 (3) | 0.035 (2) |
C4 | 0.063 (3) | 0.067 (3) | 0.077 (3) | −0.016 (2) | −0.006 (2) | 0.026 (2) |
C5 | 0.042 (2) | 0.044 (2) | 0.058 (2) | 0.0012 (17) | 0.0023 (18) | −0.0016 (17) |
C6 | 0.046 (2) | 0.0412 (19) | 0.052 (2) | 0.0007 (17) | 0.0053 (17) | −0.0032 (17) |
C7 | 0.052 (2) | 0.0403 (19) | 0.056 (2) | −0.0025 (17) | 0.0114 (18) | 0.0037 (17) |
C8 | 0.043 (2) | 0.039 (2) | 0.057 (2) | −0.0035 (16) | 0.0130 (18) | −0.0073 (16) |
C9 | 0.041 (2) | 0.044 (2) | 0.060 (2) | −0.0072 (16) | 0.0103 (18) | −0.0101 (17) |
C10 | 0.071 (3) | 0.077 (3) | 0.078 (3) | −0.026 (2) | 0.004 (2) | 0.004 (2) |
C11 | 0.085 (4) | 0.098 (4) | 0.097 (3) | −0.046 (3) | 0.010 (3) | 0.010 (3) |
C12 | 0.056 (3) | 0.080 (3) | 0.121 (4) | −0.028 (2) | 0.009 (3) | −0.009 (3) |
C13 | 0.049 (2) | 0.065 (3) | 0.107 (3) | −0.005 (2) | 0.001 (2) | −0.006 (2) |
C14 | 0.044 (2) | 0.048 (2) | 0.087 (3) | −0.0069 (18) | 0.002 (2) | 0.002 (2) |
C15 | 0.042 (2) | 0.050 (2) | 0.0436 (19) | 0.0046 (17) | 0.0033 (16) | −0.0001 (17) |
C16 | 0.045 (2) | 0.057 (2) | 0.048 (2) | 0.0066 (18) | −0.0010 (17) | 0.0009 (18) |
C17 | 0.038 (2) | 0.055 (2) | 0.049 (2) | 0.0046 (17) | 0.0073 (17) | −0.0090 (17) |
C18 | 0.044 (2) | 0.058 (2) | 0.050 (2) | 0.0012 (18) | 0.0064 (17) | −0.0136 (18) |
C19 | 0.044 (2) | 0.071 (3) | 0.068 (3) | 0.004 (2) | 0.001 (2) | −0.015 (2) |
C20 | 0.045 (3) | 0.086 (3) | 0.080 (3) | 0.008 (2) | −0.006 (2) | −0.030 (3) |
C21 | 0.048 (3) | 0.101 (4) | 0.085 (3) | −0.015 (2) | 0.019 (2) | −0.034 (3) |
C22 | 0.058 (3) | 0.096 (3) | 0.073 (3) | −0.013 (2) | 0.011 (2) | −0.007 (2) |
C23 | 0.043 (2) | 0.087 (3) | 0.070 (3) | −0.012 (2) | 0.006 (2) | −0.004 (2) |
O1 | 0.0573 (17) | 0.0555 (17) | 0.0564 (16) | −0.0011 (14) | 0.0067 (13) | 0.0061 (13) |
N1—C5 | 1.327 (4) | C10—H10 | 0.9300 |
N1—C1 | 1.327 (4) | C11—C12 | 1.364 (6) |
N2—N3 | 1.339 (3) | C11—H11 | 0.9300 |
N2—C6 | 1.344 (4) | C12—C13 | 1.360 (5) |
N2—H17 | 0.8600 | C12—H12 | 0.9300 |
N3—C8 | 1.333 (4) | C13—C14 | 1.365 (5) |
N4—C15 | 1.348 (4) | C13—H13 | 0.9300 |
N4—N5 | 1.348 (3) | C14—H14 | 0.9300 |
N4—H5 | 0.8600 | C15—C16 | 1.354 (4) |
N5—C17 | 1.340 (4) | C16—C17 | 1.393 (4) |
C1—C2 | 1.383 (4) | C16—H16 | 0.9300 |
C1—C15 | 1.453 (4) | C17—C18 | 1.457 (4) |
C2—C3 | 1.365 (5) | C18—C23 | 1.383 (5) |
C2—H2 | 0.9300 | C18—C19 | 1.387 (4) |
C3—C4 | 1.360 (5) | C19—C20 | 1.376 (5) |
C3—H3 | 0.9300 | C19—H19 | 0.9300 |
C4—C5 | 1.385 (4) | C20—C21 | 1.362 (5) |
C4—H4 | 0.9300 | C20—H20 | 0.9300 |
C5—C6 | 1.448 (4) | C21—C22 | 1.366 (5) |
C6—C7 | 1.370 (4) | C21—H21 | 0.9300 |
C7—C8 | 1.397 (4) | C22—C23 | 1.372 (5) |
C7—H7 | 0.9300 | C22—H22A | 0.9300 |
C8—C9 | 1.454 (4) | C23—H23A | 0.9300 |
C9—C14 | 1.378 (4) | O1—H22 | 0.84 (3) |
C9—C10 | 1.380 (5) | O1—H23 | 0.84 (4) |
C10—C11 | 1.378 (5) | ||
C5—N1—C1 | 118.5 (3) | C12—C11—H11 | 119.8 |
N3—N2—C6 | 113.1 (3) | C10—C11—H11 | 119.8 |
N3—N2—H17 | 123.5 | C13—C12—C11 | 119.6 (4) |
C6—N2—H17 | 123.5 | C13—C12—H12 | 120.2 |
C8—N3—N2 | 104.9 (3) | C11—C12—H12 | 120.2 |
C15—N4—N5 | 112.7 (3) | C12—C13—C14 | 120.4 (4) |
C15—N4—H5 | 123.6 | C12—C13—H13 | 119.8 |
N5—N4—H5 | 123.6 | C14—C13—H13 | 119.8 |
C17—N5—N4 | 104.2 (3) | C13—C14—C9 | 121.1 (4) |
N1—C1—C2 | 122.2 (3) | C13—C14—H14 | 119.5 |
N1—C1—C15 | 116.4 (3) | C9—C14—H14 | 119.5 |
C2—C1—C15 | 121.3 (3) | N4—C15—C16 | 106.1 (3) |
C3—C2—C1 | 118.4 (4) | N4—C15—C1 | 120.6 (3) |
C3—C2—H2 | 120.8 | C16—C15—C1 | 133.2 (3) |
C1—C2—H2 | 120.8 | C15—C16—C17 | 106.4 (3) |
C4—C3—C2 | 120.2 (4) | C15—C16—H16 | 126.8 |
C4—C3—H3 | 119.9 | C17—C16—H16 | 126.8 |
C2—C3—H3 | 119.9 | N5—C17—C16 | 110.5 (3) |
C3—C4—C5 | 118.1 (4) | N5—C17—C18 | 120.3 (3) |
C3—C4—H4 | 120.9 | C16—C17—C18 | 129.2 (3) |
C5—C4—H4 | 120.9 | C23—C18—C19 | 117.0 (3) |
N1—C5—C4 | 122.6 (3) | C23—C18—C17 | 122.5 (3) |
N1—C5—C6 | 115.9 (3) | C19—C18—C17 | 120.4 (3) |
C4—C5—C6 | 121.5 (3) | C20—C19—C18 | 121.2 (4) |
N2—C6—C7 | 105.7 (3) | C20—C19—H19 | 119.4 |
N2—C6—C5 | 120.7 (3) | C18—C19—H19 | 119.4 |
C7—C6—C5 | 133.5 (3) | C21—C20—C19 | 120.3 (4) |
C6—C7—C8 | 106.0 (3) | C21—C20—H20 | 119.8 |
C6—C7—H7 | 127.0 | C19—C20—H20 | 119.8 |
C8—C7—H7 | 127.0 | C20—C21—C22 | 119.7 (4) |
N3—C8—C7 | 110.3 (3) | C20—C21—H21 | 120.2 |
N3—C8—C9 | 121.1 (3) | C22—C21—H21 | 120.2 |
C7—C8—C9 | 128.6 (3) | C21—C22—C23 | 120.2 (4) |
C14—C9—C10 | 118.1 (3) | C21—C22—H22A | 119.9 |
C14—C9—C8 | 121.1 (3) | C23—C22—H22A | 119.9 |
C10—C9—C8 | 120.8 (3) | C22—C23—C18 | 121.5 (4) |
C11—C10—C9 | 120.3 (4) | C22—C23—H23A | 119.2 |
C11—C10—H10 | 119.8 | C18—C23—H23A | 119.2 |
C9—C10—H10 | 119.8 | H22—O1—H23 | 118 (2) |
C12—C11—C10 | 120.4 (4) | ||
C6—N2—N3—C8 | −0.7 (4) | C9—C10—C11—C12 | 0.3 (7) |
C15—N4—N5—C17 | −0.5 (3) | C10—C11—C12—C13 | −0.8 (7) |
C5—N1—C1—C2 | −0.7 (5) | C11—C12—C13—C14 | 2.1 (7) |
C5—N1—C1—C15 | 179.4 (3) | C12—C13—C14—C9 | −3.0 (6) |
N1—C1—C2—C3 | 0.7 (6) | C10—C9—C14—C13 | 2.5 (5) |
C15—C1—C2—C3 | −179.4 (3) | C8—C9—C14—C13 | −177.6 (3) |
C1—C2—C3—C4 | −0.1 (6) | N5—N4—C15—C16 | 0.1 (4) |
C2—C3—C4—C5 | −0.5 (6) | N5—N4—C15—C1 | −179.1 (3) |
C1—N1—C5—C4 | 0.1 (5) | N1—C1—C15—N4 | −3.8 (4) |
C1—N1—C5—C6 | −178.2 (3) | C2—C1—C15—N4 | 176.4 (3) |
C3—C4—C5—N1 | 0.6 (6) | N1—C1—C15—C16 | 177.3 (3) |
C3—C4—C5—C6 | 178.7 (3) | C2—C1—C15—C16 | −2.6 (6) |
N3—N2—C6—C7 | 0.4 (4) | N4—C15—C16—C17 | 0.3 (4) |
N3—N2—C6—C5 | 178.1 (3) | C1—C15—C16—C17 | 179.3 (3) |
N1—C5—C6—N2 | 4.9 (4) | N4—N5—C17—C16 | 0.7 (3) |
C4—C5—C6—N2 | −173.4 (3) | N4—N5—C17—C18 | −179.5 (3) |
N1—C5—C6—C7 | −178.1 (3) | C15—C16—C17—N5 | −0.6 (4) |
C4—C5—C6—C7 | 3.6 (6) | C15—C16—C17—C18 | 179.5 (3) |
N2—C6—C7—C8 | 0.0 (3) | N5—C17—C18—C23 | −4.3 (5) |
C5—C6—C7—C8 | −177.2 (3) | C16—C17—C18—C23 | 175.6 (3) |
N2—N3—C8—C7 | 0.7 (4) | N5—C17—C18—C19 | 173.4 (3) |
N2—N3—C8—C9 | 179.6 (3) | C16—C17—C18—C19 | −6.7 (5) |
C6—C7—C8—N3 | −0.5 (4) | C23—C18—C19—C20 | −0.8 (5) |
C6—C7—C8—C9 | −179.2 (3) | C17—C18—C19—C20 | −178.6 (3) |
N3—C8—C9—C14 | 5.3 (5) | C18—C19—C20—C21 | 0.4 (6) |
C7—C8—C9—C14 | −176.1 (3) | C19—C20—C21—C22 | −0.8 (6) |
N3—C8—C9—C10 | −174.8 (3) | C20—C21—C22—C23 | 1.6 (6) |
C7—C8—C9—C10 | 3.9 (5) | C21—C22—C23—C18 | −2.1 (6) |
C14—C9—C10—C11 | −1.2 (6) | C19—C18—C23—C22 | 1.6 (5) |
C8—C9—C10—C11 | 178.9 (4) | C17—C18—C23—C22 | 179.4 (3) |
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H22···N5i | 0.84 (3) | 2.13 (3) | 2.878 (4) | 148 (4) |
O1—H23···N3ii | 0.84 (4) | 2.20 (2) | 2.956 (4) | 150 (4) |
N2—H17···O1 | 0.86 | 2.07 | 2.918 (4) | 167 |
N4—H5···O1 | 0.86 | 2.16 | 3.007 (4) | 170 |
Symmetry codes: (i) −x, −y, −z+2; (ii) −x+1, −y, −z+2. |
Experimental details
Crystal data | |
Chemical formula | C23H17N5·H2O |
Mr | 381.43 |
Crystal system, space group | Monoclinic, P21/n |
Temperature (K) | 298 |
a, b, c (Å) | 8.0581 (17), 19.975 (2), 12.451 (2) |
β (°) | 98.273 (3) |
V (Å3) | 1983.2 (6) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.08 |
Crystal size (mm) | 0.42 × 0.11 × 0.07 |
Data collection | |
Diffractometer | Bruker SMART CCD area-detector diffractometer |
Absorption correction | Multi-scan (SADABS; Sheldrick, 2002) |
Tmin, Tmax | 0.966, 0.994 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 9869, 3513, 1796 |
Rint | 0.077 |
(sin θ/λ)max (Å−1) | 0.597 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.063, 0.159, 1.05 |
No. of reflections | 3513 |
No. of parameters | 271 |
No. of restraints | 3 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.18, −0.18 |
Computer programs: SMART (Bruker, 2001), SAINT (Bruker, 2001), SHELXTL (Sheldrick, 2008) and publCIF (Westrip, 2008).
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H22···N5i | 0.84 (3) | 2.13 (3) | 2.878 (4) | 148 (4) |
O1—H23···N3ii | 0.84 (4) | 2.20 (2) | 2.956 (4) | 150 (4) |
N2—H17···O1 | 0.86 | 2.07 | 2.918 (4) | 167 |
N4—H5···O1 | 0.86 | 2.16 | 3.007 (4) | 170 |
Symmetry codes: (i) −x, −y, −z+2; (ii) −x+1, −y, −z+2. |
References
Bruker (2001). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Dias, H. V. R. & Gamage, C. S. P. (2007). Angew. Chem. Int. Ed. 46, 2192–2194. Web of Science CSD CrossRef CAS Google Scholar
Sheldrick, G. M. (2002). SADABS. University of Göttingen, Germany. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Westrip, S. P. (2008). publCIF. In preparation. Google Scholar
Zhang, J.-P., Horike, S. & Kitagawa, S. (2007). Angew. Chem. Int. Ed. 46, 889–892. Web of Science CSD CrossRef CAS Google Scholar
Zhou, Y. B. & Chen, W. Z. (2007a). Dalton Trans. pp. 5123-5125. Web of Science CSD CrossRef Google Scholar
Zhou, Y. B. & Chen, W. Z. (2007b). Organometallics, 26, 2742–2746. Web of Science CSD CrossRef CAS Google Scholar
This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.
Pyrazolyl ligands are a kind of mutifuntional organic ligands often displaying exo-bidentate coordination mode (Dias & Gamage, 2007; Zhou & Chen, 2007a; Zhang et al., 2007). The title compound, 2,6-bis(3-phenyl-1H-pyrazol-5-yl)pyridine (hereinafter abbreviated to bppp), is a pincer-like bispyrazolyl ligand. As a kind of anionic multidentate linker, it is a suitable candidate to connect transition metals into aggregate (Zhou & Chen, 2007b).
As shown in Fig. 1, the asymmetric unit contains one bppp molecule and one water molecule, and they are linked together via N—H···O hydrogen bonds. The pyrazole rings are slightly twisted from the central pyridine ring with the dihedral angles of 5.3 (2) and 3.5 (2)°. The pyrazole and phenyl rings on each side of the molecule are also approximately coplanar with the dihedral angles of 6.0 (2) and 4.5 (2)°. Furthermore, O—H···N hydrogen bonds extend it in a one-dimensional chains running parallel to the a axis (Fig. 2). All bond lengths and angles in the title compound are normal.