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ISSN: 2056-9890

4-(2-Carb­oxy­benzo­yl)benzoic acid–4,4′-bi­pyridine (1/1)

aCollege of Chemistry and Chemical Engineering, Luoyang Normal University, Luoyang 471022, People's Republic of China
*Correspondence e-mail: jh_q128105@126.com

(Received 6 November 2008; accepted 14 November 2008; online 20 November 2008)

In the heteromolecular title compound, C15H10O5·C10H8N2, the two components are linked by O—H⋯N hydrogen bonds to form four-component ring supra­molecular assemblies. These are further inter­connected with neighbouring mol­ecules by weak inter­molecular C—H⋯π inter­actions and C—H⋯O hydrogen bonds to generate a three-dimensional network.

Related literature

For details of the C—H⋯O hydrogen bond, see: Bhogala et al. (2005[Bhogala, B. R., Basavoju, S. & Nangia, A. (2005). Cryst. Growth Des. 5, 1683-1686.]); Wang et al. (2008[Wang, Y.-T., Tang, G.-M., Zhang, Y.-C. & Wan, W.-Z. (2008). Acta Cryst. E64, o1753.]). For details of the C—H⋯π inter­action, see: Fun & Kia (2008[Fun, H.-K. & Kia, R. (2008). Acta Cryst. E64, m1116-m1117.]).

[Scheme 1]

Experimental

Crystal data
  • C15H10O5·C10H8N2

  • Mr = 426.41

  • Monoclinic, P 21 /n

  • a = 7.6883 (6) Å

  • b = 24.1886 (18) Å

  • c = 10.9560 (8) Å

  • β = 95.873 (1)°

  • V = 2026.8 (3) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 0.10 mm−1

  • T = 296 (2) K

  • 0.35 × 0.28 × 0.16 mm

Data collection
  • Bruker CCD area detector diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 1997[Bruker (1997). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.957, Tmax = 0.984

  • 10190 measured reflections

  • 3607 independent reflections

  • 2177 reflections with I > 2σ(I)

  • Rint = 0.041

Refinement
  • R[F2 > 2σ(F2)] = 0.045

  • wR(F2) = 0.128

  • S = 1.02

  • 3607 reflections

  • 292 parameters

  • H-atom parameters constrained

  • Δρmax = 0.21 e Å−3

  • Δρmin = −0.17 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C19–C24 ring.

D—H⋯A D—H H⋯A DA D—H⋯A
C8—H8⋯O4i 0.93 2.51 3.282 (3) 141
O5—H5⋯N2ii 0.82 1.84 2.641 (2) 166
O2—H2⋯N1iii 0.82 1.79 2.595 (2) 168
C1—H1⋯Cg1iv 0.93 2.54 3.449 (3) 165
Symmetry codes: (i) x+1, y, z+1; (ii) x-1, y, z; (iii) -x+1, -y, -z+2; (iv) [x-{\script{1\over 2}}, -y-{\script{1\over 2}}, z-{\script{1\over 2}}].

Data collection: SMART (Bruker, 1997[Bruker (1997). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 1997[Bruker (1997). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: SHELXTL.

Supporting information


Comment top

The asymmetric unit consists of one 4,4'-bipyridine molecule and one 4-(2-carboxylbenzoyl)benzoic acid molecule (Fig. 1). The two components are linked by O—H···N hydrogen bonds to form four-component ring supramolecular adducts (Tab. 1 & Fig. 2). The four-component ring supramolecular adducts interact with neigboring molecules via weak intermolecular C—H···π interactions and C—H···O hydrogen bonds (Tab. 1). The C—H···π interactions link the four-component ring supramolecular adducts into two-dimensional layers (Fig. 3), which are further connected by weak intermolecular C—H···O hydrogen bonds to generate a three-dimensional supramolecular structure (Fig. 4).

Related literature top

For details of the C—H···O hydrogen bond, see: Bhogala et al. (2005); Wang et al. (2008). For details of the C—H···π interaction, see: Fun & Kia (2008).

Experimental top

4,4'-bipyridine (0.1 mmol), 4-(2-carboxylbenzoyl)benzoic acid (0.1 mmol), and NaOH (0.2 mmol) were added to a H2O solution (15 ml) in a Teflon-lined stainless steel reactor. The mixture was heated at 473 K for 3 d, and then slowly cooled down to room temperature. Colorless crystals of the title compound were obtained.

Refinement top

All hydrogen atoms were positioned geometrically and treated as riding, with C—H bond lengths constrained to 0.93 Å (aromatic CH) and O—H bond lengths constrained to 0.82 Å (OH), and with Uiso(H) = 1.2Ueq(C) and Uiso(H) = 1.5Ueq(O).

Computing details top

Data collection: SMART (Bruker, 1997); cell refinement: SAINT (Bruker, 1997); data reduction: SAINT (Bruker, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. A view of the heteromolecular components of the title compound with the atom labelling scheme. Displacement ellipsoids are drawn at the 30% probability level.
[Figure 2] Fig. 2. A view of the four-component ring supramolecular adducts, formed by O—H···N hydrogen bonds.
[Figure 3] Fig. 3. A packing section of the title compound viewed down the a axis, indicating the C—H···π contacts by dashed lines.
[Figure 4] Fig. 4. A view of the molecular packing down the c axis.
4-(2-Carboxybenzoyl)benzoic acid–4,4'-bipyridine (1/1) top
Crystal data top
C15H10O5·C10H8N2F(000) = 888
Mr = 426.41Dx = 1.397 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P2ynCell parameters from 1385 reflections
a = 7.6883 (6) Åθ = 2.5–21.2°
b = 24.1886 (18) ŵ = 0.10 mm1
c = 10.9560 (8) ÅT = 296 K
β = 95.873 (1)°Block, colorless
V = 2026.8 (3) Å30.35 × 0.28 × 0.16 mm
Z = 4
Data collection top
Bruker CCD area detector
diffractometer
3607 independent reflections
Radiation source: fine-focus sealed tube2177 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.041
ϕ and ω scansθmax = 25.1°, θmin = 1.7°
Absorption correction: multi-scan
(SADABS; Bruker, 1997)
h = 99
Tmin = 0.957, Tmax = 0.984k = 2828
10190 measured reflectionsl = 137
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.045H-atom parameters constrained
wR(F2) = 0.128 w = 1/[σ2(Fo2) + (0.060P)2]
where P = (Fo2 + 2Fc2)/3
S = 1.02(Δ/σ)max < 0.001
3607 reflectionsΔρmax = 0.21 e Å3
292 parametersΔρmin = 0.17 e Å3
0 restraintsExtinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0131 (14)
Crystal data top
C15H10O5·C10H8N2V = 2026.8 (3) Å3
Mr = 426.41Z = 4
Monoclinic, P21/nMo Kα radiation
a = 7.6883 (6) ŵ = 0.10 mm1
b = 24.1886 (18) ÅT = 296 K
c = 10.9560 (8) Å0.35 × 0.28 × 0.16 mm
β = 95.873 (1)°
Data collection top
Bruker CCD area detector
diffractometer
3607 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 1997)
2177 reflections with I > 2σ(I)
Tmin = 0.957, Tmax = 0.984Rint = 0.041
10190 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0450 restraints
wR(F2) = 0.128H-atom parameters constrained
S = 1.02Δρmax = 0.21 e Å3
3607 reflectionsΔρmin = 0.17 e Å3
292 parameters
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
N10.7560 (3)0.00682 (8)0.99002 (17)0.0561 (5)
N20.9586 (2)0.15564 (8)0.46655 (17)0.0512 (5)
O10.2912 (3)0.00260 (8)0.69911 (15)0.0779 (6)
O20.3035 (3)0.06365 (7)0.84053 (15)0.0671 (5)
H20.28370.03790.88590.101*
O30.5482 (2)0.25808 (7)0.42728 (14)0.0659 (5)
O40.0942 (2)0.13238 (8)0.19022 (17)0.0789 (6)
O50.1584 (2)0.20365 (7)0.31530 (14)0.0532 (4)
H50.08220.19080.35410.080*
C10.9364 (3)0.18081 (10)0.5716 (2)0.0557 (7)
H10.94930.21900.57540.067*
C20.8955 (3)0.15357 (10)0.6751 (2)0.0530 (6)
H2A0.88100.17330.74630.064*
C30.8761 (3)0.09687 (9)0.67290 (19)0.0426 (5)
C40.8951 (3)0.07078 (10)0.5629 (2)0.0521 (6)
H40.88040.03270.55600.062*
C50.9359 (3)0.10128 (11)0.4632 (2)0.0556 (6)
H5A0.94800.08280.39010.067*
C60.8351 (3)0.06565 (9)0.7835 (2)0.0436 (6)
C70.8857 (3)0.08447 (10)0.9015 (2)0.0515 (6)
H70.94770.11740.91340.062*
C80.8436 (3)0.05426 (11)1.0008 (2)0.0571 (7)
H80.87810.06771.07910.069*
C90.7071 (3)0.01128 (10)0.8773 (2)0.0618 (7)
H90.64450.04420.86820.074*
C100.7445 (3)0.01621 (10)0.7733 (2)0.0561 (7)
H100.70890.00160.69620.067*
C110.4552 (3)0.11251 (9)0.44658 (19)0.0472 (6)
H110.48160.10160.36920.057*
C120.4068 (3)0.07337 (9)0.5287 (2)0.0503 (6)
H120.40060.03630.50600.060*
C130.3673 (3)0.08886 (9)0.64455 (19)0.0441 (6)
C140.3797 (3)0.14392 (10)0.6772 (2)0.0497 (6)
H140.35440.15480.75480.060*
C150.4293 (3)0.18291 (9)0.59573 (19)0.0481 (6)
H150.43920.21980.61940.058*
C160.4644 (3)0.16755 (9)0.47894 (19)0.0416 (5)
C170.3161 (3)0.04481 (11)0.7299 (2)0.0518 (6)
C180.5073 (3)0.21165 (10)0.3914 (2)0.0455 (6)
C190.5114 (3)0.19699 (9)0.25883 (18)0.0408 (5)
C200.6710 (3)0.20203 (9)0.2104 (2)0.0499 (6)
H200.76740.21580.25920.060*
C210.6878 (3)0.18689 (10)0.0910 (2)0.0561 (6)
H210.79570.18980.06020.067*
C220.5460 (3)0.16750 (10)0.0174 (2)0.0565 (7)
H220.55750.15760.06340.068*
C230.3861 (3)0.16268 (9)0.0633 (2)0.0499 (6)
H230.29020.14960.01290.060*
C240.3669 (3)0.17700 (9)0.18334 (19)0.0419 (5)
C250.1923 (3)0.16868 (10)0.2289 (2)0.0491 (6)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N10.0681 (14)0.0556 (14)0.0461 (12)0.0026 (11)0.0131 (10)0.0071 (10)
N20.0492 (12)0.0565 (14)0.0486 (12)0.0050 (10)0.0086 (9)0.0031 (10)
O10.1202 (17)0.0535 (12)0.0602 (12)0.0246 (11)0.0108 (10)0.0006 (10)
O20.1031 (15)0.0560 (11)0.0451 (10)0.0019 (10)0.0217 (10)0.0098 (8)
O30.0921 (14)0.0547 (12)0.0515 (11)0.0205 (10)0.0106 (9)0.0029 (9)
O40.0604 (12)0.0931 (15)0.0854 (14)0.0297 (11)0.0174 (10)0.0236 (11)
O50.0504 (10)0.0576 (11)0.0538 (11)0.0020 (8)0.0153 (8)0.0034 (8)
C10.0671 (17)0.0449 (15)0.0563 (17)0.0067 (12)0.0129 (13)0.0014 (12)
C20.0642 (16)0.0476 (15)0.0489 (15)0.0051 (12)0.0143 (12)0.0005 (11)
C30.0406 (13)0.0469 (14)0.0412 (13)0.0016 (10)0.0077 (10)0.0003 (11)
C40.0633 (16)0.0447 (14)0.0505 (15)0.0066 (12)0.0167 (12)0.0025 (11)
C50.0612 (16)0.0587 (17)0.0487 (15)0.0053 (13)0.0149 (12)0.0048 (12)
C60.0427 (13)0.0447 (14)0.0439 (13)0.0025 (10)0.0063 (10)0.0029 (11)
C70.0580 (15)0.0504 (15)0.0466 (15)0.0050 (12)0.0083 (12)0.0004 (12)
C80.0671 (17)0.0623 (18)0.0425 (14)0.0015 (14)0.0075 (12)0.0006 (13)
C90.0805 (19)0.0502 (16)0.0550 (16)0.0103 (13)0.0090 (14)0.0087 (13)
C100.0767 (18)0.0499 (16)0.0413 (14)0.0090 (13)0.0050 (12)0.0010 (11)
C110.0587 (15)0.0484 (15)0.0351 (12)0.0046 (12)0.0070 (11)0.0012 (11)
C120.0643 (16)0.0406 (14)0.0457 (14)0.0020 (11)0.0039 (12)0.0001 (11)
C130.0472 (14)0.0500 (15)0.0347 (13)0.0023 (11)0.0018 (10)0.0037 (11)
C140.0601 (15)0.0511 (15)0.0387 (13)0.0014 (12)0.0092 (11)0.0031 (11)
C150.0606 (15)0.0421 (14)0.0421 (14)0.0018 (11)0.0068 (11)0.0010 (11)
C160.0427 (13)0.0462 (14)0.0360 (12)0.0002 (10)0.0044 (10)0.0022 (10)
C170.0573 (16)0.0556 (17)0.0418 (15)0.0004 (13)0.0019 (12)0.0065 (12)
C180.0449 (14)0.0508 (16)0.0409 (13)0.0018 (11)0.0054 (10)0.0017 (11)
C190.0438 (13)0.0427 (13)0.0365 (12)0.0013 (10)0.0067 (10)0.0052 (10)
C200.0435 (14)0.0578 (16)0.0485 (14)0.0035 (11)0.0052 (11)0.0032 (12)
C210.0468 (15)0.0667 (17)0.0566 (16)0.0037 (12)0.0144 (12)0.0023 (13)
C220.0624 (17)0.0642 (17)0.0448 (14)0.0070 (13)0.0150 (13)0.0036 (12)
C230.0516 (15)0.0510 (15)0.0461 (14)0.0025 (11)0.0012 (11)0.0041 (11)
C240.0458 (14)0.0396 (13)0.0408 (13)0.0003 (10)0.0064 (11)0.0046 (10)
C250.0494 (15)0.0539 (16)0.0439 (14)0.0026 (12)0.0041 (11)0.0024 (12)
Geometric parameters (Å, º) top
N1—C91.328 (3)C9—H90.9300
N1—C81.330 (3)C10—H100.9300
N2—C51.327 (3)C11—C161.378 (3)
N2—C11.328 (3)C11—C121.383 (3)
O1—C171.205 (3)C11—H110.9300
O2—C171.308 (3)C12—C131.387 (3)
O2—H20.8200C12—H120.9300
O3—C181.220 (3)C13—C141.380 (3)
O4—C251.205 (3)C13—C171.497 (3)
O5—C251.315 (3)C14—C151.379 (3)
O5—H50.8200C14—H140.9300
C1—C21.376 (3)C15—C161.385 (3)
C1—H10.9300C15—H150.9300
C2—C31.379 (3)C16—C181.493 (3)
C2—H2A0.9300C18—C191.499 (3)
C3—C41.382 (3)C19—C201.391 (3)
C3—C61.489 (3)C19—C241.402 (3)
C4—C51.380 (3)C20—C211.377 (3)
C4—H40.9300C20—H200.9300
C5—H5A0.9300C21—C221.371 (3)
C6—C101.383 (3)C21—H210.9300
C6—C71.388 (3)C22—C231.380 (3)
C7—C81.376 (3)C22—H220.9300
C7—H70.9300C23—C241.383 (3)
C8—H80.9300C23—H230.9300
C9—C101.375 (3)C24—C251.493 (3)
C9—N1—C8117.3 (2)C14—C13—C12118.8 (2)
C5—N2—C1116.7 (2)C14—C13—C17122.7 (2)
C17—O2—H2109.5C12—C13—C17118.4 (2)
C25—O5—H5109.5C15—C14—C13120.6 (2)
N2—C1—C2123.7 (2)C15—C14—H14119.7
N2—C1—H1118.1C13—C14—H14119.7
C2—C1—H1118.1C14—C15—C16120.5 (2)
C1—C2—C3119.7 (2)C14—C15—H15119.8
C1—C2—H2A120.2C16—C15—H15119.8
C3—C2—H2A120.2C11—C16—C15119.2 (2)
C2—C3—C4116.7 (2)C11—C16—C18122.3 (2)
C2—C3—C6121.4 (2)C15—C16—C18118.6 (2)
C4—C3—C6121.9 (2)O1—C17—O2124.5 (2)
C5—C4—C3119.9 (2)O1—C17—C13123.2 (2)
C5—C4—H4120.0O2—C17—C13112.3 (2)
C3—C4—H4120.0O3—C18—C16121.2 (2)
N2—C5—C4123.2 (2)O3—C18—C19119.9 (2)
N2—C5—H5A118.4C16—C18—C19118.8 (2)
C4—C5—H5A118.4C20—C19—C24118.8 (2)
C10—C6—C7116.7 (2)C20—C19—C18117.1 (2)
C10—C6—C3121.3 (2)C24—C19—C18124.02 (18)
C7—C6—C3122.0 (2)C21—C20—C19120.7 (2)
C8—C7—C6119.7 (2)C21—C20—H20119.6
C8—C7—H7120.1C19—C20—H20119.6
C6—C7—H7120.1C22—C21—C20120.2 (2)
N1—C8—C7123.1 (2)C22—C21—H21119.9
N1—C8—H8118.4C20—C21—H21119.9
C7—C8—H8118.4C21—C22—C23120.0 (2)
N1—C9—C10123.3 (2)C21—C22—H22120.0
N1—C9—H9118.4C23—C22—H22120.0
C10—C9—H9118.4C22—C23—C24120.7 (2)
C9—C10—C6119.8 (2)C22—C23—H23119.6
C9—C10—H10120.1C24—C23—H23119.6
C6—C10—H10120.1C23—C24—C19119.49 (19)
C16—C11—C12120.3 (2)C23—C24—C25118.1 (2)
C16—C11—H11119.9C19—C24—C25122.33 (19)
C12—C11—H11119.9O4—C25—O5124.0 (2)
C11—C12—C13120.6 (2)O4—C25—C24122.1 (2)
C11—C12—H12119.7O5—C25—C24113.9 (2)
C13—C12—H12119.7
C5—N2—C1—C21.3 (3)C14—C15—C16—C18176.4 (2)
N2—C1—C2—C30.2 (4)C14—C13—C17—O1173.8 (2)
C1—C2—C3—C41.7 (3)C12—C13—C17—O17.4 (3)
C1—C2—C3—C6178.9 (2)C14—C13—C17—O26.8 (3)
C2—C3—C4—C51.6 (3)C12—C13—C17—O2172.1 (2)
C6—C3—C4—C5179.0 (2)C11—C16—C18—O3165.6 (2)
C1—N2—C5—C41.5 (3)C15—C16—C18—O315.8 (3)
C3—C4—C5—N20.0 (4)C11—C16—C18—C1910.3 (3)
C2—C3—C6—C10151.9 (2)C15—C16—C18—C19168.35 (19)
C4—C3—C6—C1027.6 (3)O3—C18—C19—C2059.3 (3)
C2—C3—C6—C728.2 (3)C16—C18—C19—C20116.6 (2)
C4—C3—C6—C7152.4 (2)O3—C18—C19—C24123.0 (2)
C10—C6—C7—C80.5 (3)C16—C18—C19—C2461.1 (3)
C3—C6—C7—C8179.6 (2)C24—C19—C20—C210.9 (3)
C9—N1—C8—C70.4 (4)C18—C19—C20—C21176.9 (2)
C6—C7—C8—N10.3 (4)C19—C20—C21—C221.1 (4)
C8—N1—C9—C100.7 (4)C20—C21—C22—C230.5 (4)
N1—C9—C10—C60.9 (4)C21—C22—C23—C240.3 (4)
C7—C6—C10—C90.7 (3)C22—C23—C24—C190.4 (3)
C3—C6—C10—C9179.3 (2)C22—C23—C24—C25177.6 (2)
C16—C11—C12—C130.2 (3)C20—C19—C24—C230.2 (3)
C11—C12—C13—C140.9 (3)C18—C19—C24—C23177.5 (2)
C11—C12—C13—C17179.8 (2)C20—C19—C24—C25178.1 (2)
C12—C13—C14—C150.4 (3)C18—C19—C24—C250.4 (3)
C17—C13—C14—C15179.3 (2)C23—C24—C25—O430.4 (3)
C13—C14—C15—C161.2 (3)C19—C24—C25—O4147.5 (2)
C12—C11—C16—C151.7 (3)C23—C24—C25—O5150.7 (2)
C12—C11—C16—C18176.9 (2)C19—C24—C25—O531.3 (3)
C14—C15—C16—C112.2 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C8—H8···O4i0.932.513.282 (3)141
O5—H5···N2ii0.821.842.641 (2)166
O2—H2···N1iii0.821.792.595 (2)168
C1—H1···Cg1iv0.932.543.449 (3)165
Symmetry codes: (i) x+1, y, z+1; (ii) x1, y, z; (iii) x+1, y, z+2; (iv) x1/2, y1/2, z1/2.

Experimental details

Crystal data
Chemical formulaC15H10O5·C10H8N2
Mr426.41
Crystal system, space groupMonoclinic, P21/n
Temperature (K)296
a, b, c (Å)7.6883 (6), 24.1886 (18), 10.9560 (8)
β (°) 95.873 (1)
V3)2026.8 (3)
Z4
Radiation typeMo Kα
µ (mm1)0.10
Crystal size (mm)0.35 × 0.28 × 0.16
Data collection
DiffractometerBruker CCD area detector
diffractometer
Absorption correctionMulti-scan
(SADABS; Bruker, 1997)
Tmin, Tmax0.957, 0.984
No. of measured, independent and
observed [I > 2σ(I)] reflections
10190, 3607, 2177
Rint0.041
(sin θ/λ)max1)0.597
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.045, 0.128, 1.02
No. of reflections3607
No. of parameters292
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.21, 0.17

Computer programs: SMART (Bruker, 1997), SAINT (Bruker, 1997), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C8—H8···O4i0.932.513.282 (3)141.1
O5—H5···N2ii0.821.842.641 (2)165.6
O2—H2···N1iii0.821.792.595 (2)167.6
C1—H1···Cg1iv0.932.543.449 (3)165
Symmetry codes: (i) x+1, y, z+1; (ii) x1, y, z; (iii) x+1, y, z+2; (iv) x1/2, y1/2, z1/2.
 

Acknowledgements

The authors thank Luoyang Normal University for supporting this work.

References

First citationBhogala, B. R., Basavoju, S. & Nangia, A. (2005). Cryst. Growth Des. 5, 1683–1686.  Web of Science CSD CrossRef CAS Google Scholar
First citationBruker (1997). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.  Google Scholar
First citationFun, H.-K. & Kia, R. (2008). Acta Cryst. E64, m1116–m1117.  Web of Science CSD CrossRef IUCr Journals Google Scholar
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
First citationWang, Y.-T., Tang, G.-M., Zhang, Y.-C. & Wan, W.-Z. (2008). Acta Cryst. E64, o1753.  Web of Science CSD CrossRef IUCr Journals Google Scholar

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