organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890

2′,6′-Bis(4-carb­­oxy­phen­yl)-4,4′-bipyridin-1-ium nitrate 0.25-hydrate

aDepartment of Ophthalmology, The Second Hospital of Jilin University, Changchun 130041, People's Republic of China, and bDepartment of Orthopedics, The China–Japan Union Hospital of Jilin University, Changchun 130033, People's Republic of China
*Correspondence e-mail: doctorzang@163.com

(Received 22 November 2011; accepted 30 November 2011; online 7 December 2011)

In the title compound, C24H17N2O4+·NO3·0.25H2O, the central pyridine ring of the 2′,6′-bis­(4-carb­oxy­phen­yl)-4,4′-bipyridin-1-ium cation is almost coplanar with one benzene ring [dihedral angle = 1.03 (5)°], while it makes dihedral angles of 9.59 (5)° with the other benzene ring and 13.66 (6)° with the pyridinium ring. In the crystal, N—H⋯O and O—H⋯O hydrogen bonds link the cations and nitrate anions into a sheet in the (302) plane. The crystal structure also exhibits ππ inter­actions between the central pyridine ring and the benzene rings of neighboring mol­ecules [centroid–centroid distance = 3.6756 (13) Å].

Related literature

For the properties and applications of mol­ecular-ionic crystals, see: Katrusiak & Szafrański (2006[Katrusiak, A. & Szafrański, M. (2006). J. Am. Chem. Soc. 128, 15775-15785.]); Liao et al. (2008[Liao, C. Y., Chan, K. T., Chiu, P. L., Chen, C. Y. & Lee, H. M. (2008). Inorg. Chim. Acta, 361, 2973-2978.]); Wang (2010[Wang, B. (2010). Acta Cryst. E66, o1473.]).

[Scheme 1]

Experimental

Crystal data
  • C24H17N2O4+·NO3·0.25H2O

  • Mr = 463.91

  • Monoclinic, P 21 /c

  • a = 13.6978 (11) Å

  • b = 16.0688 (12) Å

  • c = 9.6354 (8) Å

  • β = 92.696 (1)°

  • V = 2118.5 (3) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 0.11 mm−1

  • T = 293 K

  • 0.25 × 0.21 × 0.20 mm

Data collection
  • Bruker APEXII CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2001[Bruker (2001). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.973, Tmax = 0.978

  • 11529 measured reflections

  • 4158 independent reflections

  • 2605 reflections with I > 2σ(I)

  • Rint = 0.040

Refinement
  • R[F2 > 2σ(F2)] = 0.050

  • wR(F2) = 0.150

  • S = 1.04

  • 4158 reflections

  • 316 parameters

  • H-atom parameters constrained

  • Δρmax = 0.30 e Å−3

  • Δρmin = −0.27 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
N1—H1⋯O5i 0.86 1.84 2.697 (2) 171
O2—H2A⋯O3ii 0.82 1.93 2.728 (2) 163
O4—H4⋯O5 0.82 1.78 2.598 (2) 173
O1W—H1A⋯O1Wiii 0.92 2.14 2.963 (18) 149
O1W—H1B⋯O1iv 0.90 2.22 3.059 (8) 154
Symmetry codes: (i) x, y+1, z; (ii) -x+1, -y+1, -z+1; (iii) -x+1, -y+2, -z; (iv) -x+1, -y+2, -z+1.

Data collection: APEX2 (Bruker, 2007[Bruker (2007). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2007[Bruker (2007). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXTL; molecular graphics: XP in SHELXTL and Mercury (Macrae et al., 2006[Macrae, C. F., Edgington, P. R., McCabe, P., Pidcock, E., Shields, G. P., Taylor, R., Towler, M. & van de Streek, J. (2006). J. Appl. Cryst. 39, 453-457.]); software used to prepare material for publication: SHELXTL.

Supporting information


Comment top

Recently much attention has been devoted to simple molecular-ionic crystals containing organic cations and anions due to the tunability of their special structural features and their interesting physical properties (Katrusiak & Szafrański, 2006; Wang, 2010). Molecular building blocks associated with pyridine carboxylic acids are widely used in chiral catalysis, photoelectronic materials, hematopathology and medicine (Liao et al., 2008). In our laboratory, the compound containing a 2,6-bis(4-carboxyphenyl)-4,4'-bipyridinium cation, an NO3- anion and quarter water molecules has been synthesized and its crystal structure is reported here.

In the title compound (Fig. 1), the central pyridine ring of the cation is almost coplanar with one benzene ring, making a dihedral angle of 1.03 (5)°, while it makes dihedral angles of 9.59 (5)° with the other benzene ring and 13.66 (6)° with the protonated pyridinium ring. N—H···O and O—H···O hydrogen bonds link the organic cations and nitrate anions into a one-dimensional ribbon along [0 1 0] (Fig. 2). The crystal structure also exhibits ππ interactions between the central pyridine rings and the benzene rings of neighboring molecules [centroid–centroid distance = 3.6756 (13) Å].

Related literature top

For the properties and applications of molecular-ionic crystals, see: Katrusiak & Szafrański (2006); Liao et al. (2008); Wang (2010).

Experimental top

A mixture of 2,6-di-4-carboxyphenyl-4,4'-bipyridine (0.2 mmol, 0.080 g), nitric acid (0.5 ml, 6 mol/L), ethanol (10 ml) and H2O (5 ml) was stirred for 10 min. A small amount of white precipitate was filtered off and the filtrate was kept for several days at ambient conditions. Colorless block crystals of the title compound were isolated.

Refinement top

H atoms on C and N atoms were positioned geometrically and refined as riding atoms, with C—H = 0.93 and N—H = 0.86 Å and with Uiso(H) = 1.2Ueq(C, N). According to the electron density and element analysis, the site occupation factor of the water molecule was fixed at 0.25. H atoms of the water molecule were set to an arbitrary postion and refined as riding atoms, with Uiso(H) = 1.5Ueq(O).

Computing details top

Data collection: APEX2 (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: XP in SHELXTL (Sheldrick, 2008) and Mercury (Macrae et al., 2006); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. The molecular structure of the title compound. Displacement ellipsoids are drawn at the 50% probability level.
[Figure 2] Fig. 2. View of the one-dimensional ribbon structure of the title compound built by hydrogen bonds (dashed lines).
2',6'-Bis(4-carboxyphenyl)-4,4'-bipyridin-1-ium nitrate hydrate top
Crystal data top
C24H17N2O4+·NO3·0.25H2OF(000) = 962
Mr = 463.91Dx = 1.454 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 4158 reflections
a = 13.6978 (11) Åθ = 1.0–26.0°
b = 16.0688 (12) ŵ = 0.11 mm1
c = 9.6354 (8) ÅT = 293 K
β = 92.696 (1)°Block, colorless
V = 2118.5 (3) Å30.25 × 0.21 × 0.20 mm
Z = 4
Data collection top
Bruker APEXII CCD
diffractometer
4158 independent reflections
Radiation source: fine-focus sealed tube2605 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.040
ϕ and ω scansθmax = 26.0°, θmin = 2.0°
Absorption correction: multi-scan
(SADABS; Bruker, 2001)
h = 1616
Tmin = 0.973, Tmax = 0.978k = 1917
11529 measured reflectionsl = 911
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.050Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.150H-atom parameters constrained
S = 1.04 w = 1/[σ2(Fo2) + (0.0724P)2 + 0.0957P]
where P = (Fo2 + 2Fc2)/3
4158 reflections(Δ/σ)max < 0.001
316 parametersΔρmax = 0.30 e Å3
0 restraintsΔρmin = 0.27 e Å3
Crystal data top
C24H17N2O4+·NO3·0.25H2OV = 2118.5 (3) Å3
Mr = 463.91Z = 4
Monoclinic, P21/cMo Kα radiation
a = 13.6978 (11) ŵ = 0.11 mm1
b = 16.0688 (12) ÅT = 293 K
c = 9.6354 (8) Å0.25 × 0.21 × 0.20 mm
β = 92.696 (1)°
Data collection top
Bruker APEXII CCD
diffractometer
4158 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2001)
2605 reflections with I > 2σ(I)
Tmin = 0.973, Tmax = 0.978Rint = 0.040
11529 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0500 restraints
wR(F2) = 0.150H-atom parameters constrained
S = 1.04Δρmax = 0.30 e Å3
4158 reflectionsΔρmin = 0.27 e Å3
316 parameters
Special details top

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 (Å2) top
xyzUiso*/UeqOcc. (<1)
C10.42765 (16)0.78749 (14)0.5913 (2)0.0286 (5)
C20.46419 (18)0.71363 (14)0.5406 (3)0.0334 (6)
H20.44040.66310.57150.040*
C30.53576 (18)0.71478 (14)0.4445 (3)0.0337 (6)
H30.55970.66470.41170.040*
C40.57286 (16)0.78937 (13)0.3957 (2)0.0258 (5)
C50.53495 (17)0.86287 (14)0.4469 (3)0.0330 (6)
H50.55790.91350.41520.040*
C60.46397 (17)0.86229 (14)0.5438 (2)0.0322 (6)
H60.44040.91230.57740.039*
C70.35134 (17)0.78863 (14)0.6971 (3)0.0321 (6)
C80.65044 (16)0.78741 (13)0.2920 (2)0.0254 (5)
C90.69124 (16)0.85873 (14)0.2365 (2)0.0279 (5)
H90.67110.91100.26510.033*
C100.76210 (16)0.85180 (13)0.1382 (2)0.0260 (5)
C110.78848 (16)0.77208 (14)0.0987 (2)0.0273 (5)
H110.83520.76480.03270.033*
C120.74523 (16)0.70341 (13)0.1575 (2)0.0249 (5)
C130.80567 (16)0.92684 (13)0.0741 (2)0.0261 (5)
C140.7948 (2)1.00598 (14)0.1296 (3)0.0438 (7)
H140.76111.01280.21040.053*
C150.8333 (2)1.07395 (15)0.0661 (3)0.0460 (7)
H150.82481.12670.10330.055*
C160.89662 (18)0.99033 (13)0.1044 (3)0.0328 (6)
H160.93190.98560.18420.039*
C170.85909 (17)0.92067 (14)0.0450 (2)0.0306 (6)
H170.86930.86880.08440.037*
C180.76886 (16)0.61666 (13)0.1168 (2)0.0247 (5)
C190.71249 (16)0.55022 (14)0.1607 (2)0.0295 (5)
H190.65970.56060.21540.035*
C200.73369 (16)0.46961 (14)0.1246 (2)0.0303 (6)
H200.69580.42620.15630.036*
C210.81127 (16)0.45261 (13)0.0410 (2)0.0272 (5)
C220.86680 (18)0.51865 (14)0.0048 (3)0.0323 (6)
H220.91820.50830.06220.039*
C230.84681 (16)0.59942 (14)0.0335 (2)0.0301 (6)
H230.88570.64270.00360.036*
C240.83576 (16)0.36588 (14)0.0027 (2)0.0286 (5)
N10.88275 (14)1.06493 (12)0.0482 (2)0.0337 (5)
H10.90641.10820.08690.040*
N20.67797 (13)0.71123 (10)0.25346 (19)0.0260 (4)
N30.99617 (14)0.19689 (12)0.2573 (2)0.0312 (5)
O20.31962 (13)0.71380 (10)0.72797 (19)0.0456 (5)
H2A0.27810.71760.78630.068*
O10.32181 (13)0.85207 (11)0.74803 (19)0.0469 (5)
O40.89796 (12)0.36227 (9)0.09689 (18)0.0387 (5)
H40.90940.31350.11480.058*
O30.80256 (12)0.30430 (9)0.05852 (18)0.0350 (4)
O50.94948 (15)0.21008 (10)0.14753 (19)0.0496 (5)
O61.02518 (13)0.25580 (11)0.32456 (19)0.0451 (5)
O71.01033 (13)0.12364 (10)0.28914 (18)0.0428 (5)
O1W0.5358 (6)1.0131 (4)0.1459 (10)0.062 (2)0.25
H1A0.53590.99430.05560.092*0.25
H1B0.56831.06180.15480.092*0.25
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0288 (13)0.0303 (13)0.0272 (13)0.0037 (10)0.0056 (10)0.0019 (10)
C20.0407 (14)0.0244 (13)0.0365 (15)0.0024 (10)0.0156 (12)0.0025 (10)
C30.0403 (14)0.0224 (12)0.0398 (15)0.0029 (10)0.0149 (12)0.0015 (10)
C40.0257 (12)0.0270 (12)0.0248 (13)0.0015 (9)0.0037 (10)0.0004 (9)
C50.0345 (14)0.0245 (13)0.0407 (15)0.0012 (10)0.0095 (12)0.0001 (11)
C60.0363 (14)0.0243 (13)0.0367 (15)0.0064 (10)0.0100 (11)0.0032 (10)
C70.0315 (13)0.0303 (14)0.0351 (15)0.0043 (11)0.0084 (11)0.0037 (11)
C80.0256 (12)0.0234 (12)0.0274 (13)0.0015 (9)0.0030 (10)0.0001 (9)
C90.0318 (13)0.0221 (12)0.0305 (13)0.0007 (10)0.0091 (10)0.0036 (10)
C100.0278 (12)0.0246 (12)0.0259 (13)0.0004 (10)0.0038 (10)0.0009 (9)
C110.0257 (12)0.0264 (12)0.0304 (13)0.0010 (10)0.0072 (10)0.0011 (10)
C120.0256 (12)0.0243 (12)0.0249 (13)0.0010 (9)0.0024 (10)0.0010 (9)
C130.0268 (12)0.0213 (12)0.0305 (13)0.0003 (9)0.0051 (10)0.0005 (9)
C140.0612 (18)0.0250 (14)0.0480 (17)0.0023 (12)0.0325 (14)0.0033 (11)
C150.0628 (18)0.0240 (14)0.0538 (18)0.0013 (12)0.0293 (15)0.0022 (12)
C160.0391 (14)0.0277 (13)0.0327 (14)0.0011 (11)0.0119 (12)0.0005 (11)
C170.0363 (13)0.0225 (12)0.0333 (14)0.0019 (10)0.0063 (11)0.0026 (10)
C180.0258 (12)0.0208 (12)0.0276 (13)0.0004 (9)0.0033 (10)0.0023 (9)
C190.0273 (12)0.0264 (13)0.0361 (14)0.0012 (10)0.0134 (10)0.0006 (10)
C200.0305 (13)0.0223 (12)0.0389 (15)0.0031 (10)0.0098 (11)0.0020 (10)
C210.0290 (12)0.0229 (12)0.0300 (13)0.0015 (10)0.0047 (10)0.0012 (10)
C220.0329 (13)0.0294 (13)0.0357 (14)0.0005 (11)0.0147 (11)0.0011 (11)
C230.0327 (13)0.0200 (12)0.0384 (14)0.0020 (10)0.0121 (11)0.0021 (10)
C240.0282 (13)0.0260 (13)0.0321 (14)0.0001 (10)0.0057 (11)0.0004 (10)
N10.0399 (12)0.0244 (11)0.0380 (12)0.0038 (9)0.0146 (10)0.0045 (9)
N20.0272 (10)0.0231 (10)0.0278 (11)0.0014 (8)0.0043 (8)0.0005 (8)
N30.0333 (11)0.0273 (11)0.0338 (12)0.0033 (9)0.0089 (9)0.0009 (9)
O20.0508 (11)0.0341 (10)0.0541 (13)0.0027 (8)0.0271 (10)0.0052 (9)
O10.0550 (12)0.0346 (10)0.0534 (13)0.0088 (9)0.0277 (10)0.0016 (9)
O40.0485 (10)0.0250 (9)0.0446 (11)0.0010 (8)0.0218 (9)0.0032 (8)
O30.0389 (10)0.0240 (9)0.0431 (11)0.0011 (7)0.0141 (8)0.0018 (7)
O50.0812 (14)0.0267 (10)0.0441 (12)0.0023 (9)0.0370 (11)0.0029 (8)
O60.0528 (12)0.0370 (10)0.0466 (12)0.0102 (9)0.0156 (9)0.0122 (9)
O70.0522 (12)0.0295 (10)0.0482 (12)0.0052 (8)0.0181 (9)0.0051 (8)
O1W0.069 (5)0.023 (4)0.093 (7)0.006 (4)0.002 (5)0.010 (4)
Geometric parameters (Å, º) top
C1—C21.386 (3)C15—N11.328 (3)
C1—C61.387 (3)C15—H150.9300
C1—C71.495 (3)C16—N11.333 (3)
C2—C31.380 (3)C16—C171.369 (3)
C2—H20.9300C16—H160.9300
C3—C41.392 (3)C17—H170.9300
C3—H30.9300C18—C231.393 (3)
C4—C51.390 (3)C18—C191.395 (3)
C4—C81.493 (3)C19—C201.376 (3)
C5—C61.379 (3)C19—H190.9300
C5—H50.9300C20—C211.390 (3)
C6—H60.9300C20—H200.9300
C7—O11.209 (3)C21—C221.390 (3)
C7—O21.317 (3)C21—C241.484 (3)
C8—N21.338 (3)C22—C231.380 (3)
C8—C91.393 (3)C22—H220.9300
C9—C101.392 (3)C23—H230.9300
C9—H90.9300C24—O31.224 (3)
C10—C111.389 (3)C24—O41.314 (3)
C10—C131.492 (3)N1—H10.8600
C11—C121.386 (3)N3—O61.224 (2)
C11—H110.9300N3—O71.234 (2)
C12—N21.341 (3)N3—O51.279 (2)
C12—C181.488 (3)O2—H2A0.8200
C13—C141.390 (3)O4—H40.8200
C13—C171.393 (3)O1W—H1A0.9210
C14—C151.370 (3)O1W—H1B0.9027
C14—H140.9300
C2—C1—C6119.0 (2)C13—C14—H14119.8
C2—C1—C7121.8 (2)N1—C15—C14120.4 (2)
C6—C1—C7119.2 (2)N1—C15—H15119.8
C3—C2—C1120.3 (2)C14—C15—H15119.8
C3—C2—H2119.8N1—C16—C17120.1 (2)
C1—C2—H2119.8N1—C16—H16119.9
C2—C3—C4121.3 (2)C17—C16—H16119.9
C2—C3—H3119.3C16—C17—C13120.6 (2)
C4—C3—H3119.3C16—C17—H17119.7
C5—C4—C3117.6 (2)C13—C17—H17119.7
C5—C4—C8123.0 (2)C23—C18—C19118.2 (2)
C3—C4—C8119.4 (2)C23—C18—C12121.34 (19)
C6—C5—C4121.4 (2)C19—C18—C12120.5 (2)
C6—C5—H5119.3C20—C19—C18121.2 (2)
C4—C5—H5119.3C20—C19—H19119.4
C5—C6—C1120.3 (2)C18—C19—H19119.4
C5—C6—H6119.9C19—C20—C21120.5 (2)
C1—C6—H6119.9C19—C20—H20119.7
O1—C7—O2123.9 (2)C21—C20—H20119.7
O1—C7—C1123.0 (2)C22—C21—C20118.6 (2)
O2—C7—C1113.0 (2)C22—C21—C24120.3 (2)
N2—C8—C9121.5 (2)C20—C21—C24121.1 (2)
N2—C8—C4115.06 (19)C23—C22—C21120.9 (2)
C9—C8—C4123.41 (19)C23—C22—H22119.5
C10—C9—C8120.0 (2)C21—C22—H22119.5
C10—C9—H9120.0C22—C23—C18120.5 (2)
C8—C9—H9120.0C22—C23—H23119.7
C11—C10—C9117.3 (2)C18—C23—H23119.7
C11—C10—C13121.2 (2)O3—C24—O4123.5 (2)
C9—C10—C13121.5 (2)O3—C24—C21123.8 (2)
C12—C11—C10120.0 (2)O4—C24—C21112.65 (19)
C12—C11—H11120.0C15—N1—C16121.6 (2)
C10—C11—H11120.0C15—N1—H1119.2
N2—C12—C11121.9 (2)C16—N1—H1119.2
N2—C12—C18115.74 (19)C8—N2—C12119.23 (19)
C11—C12—C18122.4 (2)O6—N3—O7123.2 (2)
C14—C13—C17116.9 (2)O6—N3—O5119.81 (19)
C14—C13—C10121.8 (2)O7—N3—O5117.02 (18)
C17—C13—C10121.3 (2)C7—O2—H2A109.5
C15—C14—C13120.5 (2)C24—O4—H4109.5
C15—C14—H14119.8H1A—O1W—H1B110.5
C6—C1—C2—C30.1 (4)C17—C13—C14—C151.6 (4)
C7—C1—C2—C3178.9 (2)C10—C13—C14—C15178.2 (2)
C1—C2—C3—C40.2 (4)C13—C14—C15—N10.9 (4)
C2—C3—C4—C50.2 (4)N1—C16—C17—C130.4 (4)
C2—C3—C4—C8179.9 (2)C14—C13—C17—C161.4 (4)
C3—C4—C5—C60.7 (4)C10—C13—C17—C16178.4 (2)
C8—C4—C5—C6179.4 (2)N2—C12—C18—C23170.8 (2)
C4—C5—C6—C10.8 (4)C11—C12—C18—C2310.3 (3)
C2—C1—C6—C50.4 (4)N2—C12—C18—C199.7 (3)
C7—C1—C6—C5179.5 (2)C11—C12—C18—C19169.2 (2)
C2—C1—C7—O1176.2 (2)C23—C18—C19—C200.8 (3)
C6—C1—C7—O12.9 (4)C12—C18—C19—C20179.7 (2)
C2—C1—C7—O24.2 (4)C18—C19—C20—C211.1 (4)
C6—C1—C7—O2176.7 (2)C19—C20—C21—C220.1 (4)
C5—C4—C8—N2179.6 (2)C19—C20—C21—C24179.2 (2)
C3—C4—C8—N20.3 (3)C20—C21—C22—C231.2 (4)
C5—C4—C8—C90.5 (4)C24—C21—C22—C23177.9 (2)
C3—C4—C8—C9179.4 (2)C21—C22—C23—C181.5 (4)
N2—C8—C9—C100.3 (3)C19—C18—C23—C220.4 (3)
C4—C8—C9—C10178.8 (2)C12—C18—C23—C22179.1 (2)
C8—C9—C10—C110.6 (3)C22—C21—C24—O3166.1 (2)
C8—C9—C10—C13178.5 (2)C20—C21—C24—O313.0 (4)
C9—C10—C11—C120.5 (3)C22—C21—C24—O413.2 (3)
C13—C10—C11—C12178.5 (2)C20—C21—C24—O4167.7 (2)
C10—C11—C12—N20.3 (3)C14—C15—N1—C160.1 (4)
C10—C11—C12—C18178.5 (2)C17—C16—N1—C150.4 (4)
C11—C10—C13—C14167.6 (2)C9—C8—N2—C121.1 (3)
C9—C10—C13—C1414.5 (4)C4—C8—N2—C12178.05 (19)
C11—C10—C13—C1712.6 (3)C11—C12—N2—C81.2 (3)
C9—C10—C13—C17165.3 (2)C18—C12—N2—C8177.77 (19)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1···O5i0.861.842.697 (2)171
O2—H2A···O3ii0.821.932.728 (2)163
O4—H4···O50.821.782.598 (2)173
O1W—H1A···O1Wiii0.922.142.963 (18)149
O1W—H1B···O1iv0.902.223.059 (8)154
Symmetry codes: (i) x, y+1, z; (ii) x+1, y+1, z+1; (iii) x+1, y+2, z; (iv) x+1, y+2, z+1.

Experimental details

Crystal data
Chemical formulaC24H17N2O4+·NO3·0.25H2O
Mr463.91
Crystal system, space groupMonoclinic, P21/c
Temperature (K)293
a, b, c (Å)13.6978 (11), 16.0688 (12), 9.6354 (8)
β (°) 92.696 (1)
V3)2118.5 (3)
Z4
Radiation typeMo Kα
µ (mm1)0.11
Crystal size (mm)0.25 × 0.21 × 0.20
Data collection
DiffractometerBruker APEXII CCD
diffractometer
Absorption correctionMulti-scan
(SADABS; Bruker, 2001)
Tmin, Tmax0.973, 0.978
No. of measured, independent and
observed [I > 2σ(I)] reflections
11529, 4158, 2605
Rint0.040
(sin θ/λ)max1)0.617
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.050, 0.150, 1.04
No. of reflections4158
No. of parameters316
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.30, 0.27

Computer programs: APEX2 (Bruker, 2007), SAINT (Bruker, 2007), XP in SHELXTL (Sheldrick, 2008) and Mercury (Macrae et al., 2006).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1···O5i0.861.842.697 (2)171
O2—H2A···O3ii0.821.932.728 (2)163
O4—H4···O50.821.782.598 (2)173
O1W—H1A···O1Wiii0.922.142.963 (18)149
O1W—H1B···O1iv0.902.223.059 (8)154
Symmetry codes: (i) x, y+1, z; (ii) x+1, y+1, z+1; (iii) x+1, y+2, z; (iv) x+1, y+2, z+1.
 

Acknowledgements

The authors thank Jilin University for supporting this work.

References

First citationBruker (2001). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
First citationBruker (2007). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
First citationKatrusiak, A. & Szafrański, M. (2006). J. Am. Chem. Soc. 128, 15775–15785.  Web of Science CSD CrossRef PubMed CAS
First citationLiao, C. Y., Chan, K. T., Chiu, P. L., Chen, C. Y. & Lee, H. M. (2008). Inorg. Chim. Acta, 361, 2973–2978.  Web of Science CSD CrossRef CAS
First citationMacrae, C. F., Edgington, P. R., McCabe, P., Pidcock, E., Shields, G. P., Taylor, R., Towler, M. & van de Streek, J. (2006). J. Appl. Cryst. 39, 453–457.  Web of Science CrossRef CAS IUCr Journals
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals
First citationWang, B. (2010). Acta Cryst. E66, o1473.  Web of Science CSD CrossRef IUCr Journals

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