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The title compound, C12H13N2+·NO3-·3H2O [where C12H13N2+ is the monoprotonated form of 1,2-bis(4-pyridyl)­ethane (BPEH+)] is monoclinic, space group P21/c, and contains two empirical formulae in the asymmetric unit. The compound has cationic [BPEH]nn+ organic layers, alternating in the b direction with anionic [(NO3)·3H2O]nn- inorganic layers. Hydro­gen bonds between 4-pyridyl and 4-pyridinium groups, and between nitrate ions and water mol­ecules, give rise to chains and two-dimensional hydrogen-bonding networks, respectively.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536803000783/cf6229sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536803000783/cf6229Isup2.hkl
Contains datablock I

CCDC reference: 204679

Key indicators

  • Single-crystal X-ray study
  • T = 180 K
  • Mean [sigma](C-C) = 0.003 Å
  • R factor = 0.076
  • wR factor = 0.222
  • Data-to-parameter ratio = 12.5

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry


Yellow Alert Alert Level C:
DIFMX_01 Alert C The maximum difference density is > 0.1*ZMAX*0.75 _refine_diff_density_max given = 0.707 Test value = 0.600 DIFMX_02 Alert C The minimum difference density is > 0.1*ZMAX*0.75 The relevant atom site should be identified.
0 Alert Level A = Potentially serious problem
0 Alert Level B = Potential problem
2 Alert Level C = Please check

Comment top

1,2-Bis(4-pyridyl)ethane (BPE) has been successfully employed in the synthesis of novel metal–organic frameworks (see, for example, Fujita et al., 1994; Wang et al., 1999; Bourne et al., 2001). We have focused our attention on this organic ligand to obtain novel crystal structures with Cd2+ and Co2+ ions, produced under hydrothermal conditions and in the presence of carboxylic acids and triethylamine (TEA) (Almeida Paz et al., 2002, 2002a). We have also found that, under the same experimental conditions, the absence of TEA can lead to the formation of a double-layered salt of BPE with trimesic acid residues (Almeida Paz et al., 2002b). The title compound, (I), was obtained in the presence of Cd2+ ions and, to our knowledge, is the first crystal structure of a BPE salt with a typical inorganic ion (NO3).

The structure determination of (I) reveals the presence of two BPE molecules in the asymmetric unit, both present in the typical anti conformation (Hennigar et al., 1997) and with one protonated 4-pyridyl group, BPEH+ (Fig. 1). Adjacent BPEH+ cations are linked via strong N+—H···N hydrogen bonds (Table 2), forming an infinite one-dimensional chain, which runs along the a direction (Fig. 2). These chains are close-packed in the ab plane, generating a positively charged [BPEH]nn+ organic layer, which alternates with an inorganic layer composed of nitrate ions and water molecules (Figs. 3 and 4). This negatively charged inorganic layer, [(NO3)·3H2O]nn-, is formed by an extensive and strong hydrogen-bonding network (Table 2), and can be described as the alternation of two graph sets, R68(14) and R66(14) (Fig. 3). In this layer, each water O atom acts as a single acceptor (with an adjacent water molecule) and as a double donor, donating the attached H atoms to a neighbouring water molecule and a nitrate ion (Fig. 3). An interesting feature in the crystal structure arises from the bifurcated donor nature of atoms O6W and O9W, with H6A and H9A, respectively, being almost equidistant from the O atoms in the neighbouring nitrate ions (Table 2). This suggests that the hydrogen-bonding interactions are very likely to be between the water molecules and the conjugated π system in the nitrate ions (Fig. 3, top).

Experimental top

All chemicals were obtained from commercial sources and were used as received. To a solution of Cd(NO3)2·4H2O (0.629 g, Aldrich) in distilled water (11.60 g), 1,2-bis(4-pyridyl)ethane (BPE, 0.382 g, Aldrich) was added, and the resulting mixture was stirred thoroughly for 1 h at ambient temperature. The suspension, with a Cd2+:BPE:H2O molar ratio of 1.00:1.02:315, was placed in a Parr stainless steel teflon-lined reaction vessel (21 ml, 70% full). The reaction was performed under autogeneous pressure and static conditions in a preheated oven at 418 K, using a previously reported temperature profile (Almeida Paz et al., 2002). The microcrystalline product was placed inside a refrigerator for 24 h, after which crystals of the title compound were separated manually.

Refinement top

H atoms bound to C atoms were placed in calculated positions and allowed to ride during subsequent refinement, with Uiso(H) = 1.2Ueq(C). H atoms bonded to N and O atoms were located in difference Fourier maps and refined with a single isotropic displacement parameter common to all H atoms. N—H distances were restrained to 0.88 Å. O—H and H···H distances were also restrained, in order to ensure a reasonable geometry for the water molecules.

Computing details top

Data collection: COLLECT (Nonius, 1998); cell refinement: HKL SCALEPACK (Otwinowski & Minor, 1997); data reduction: HKL DENZO (Otwinowski & Minor, 1997) and SCALEPACK; program(s) used to solve structure: SIR92 (Altomare et al., 1994); program(s) used to refine structure: SHELXTL (Bruker, 2001); molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Figures top
[Figure 1] Fig. 1. The asymmetric unit of (I), with displacement ellipsoids drawn at the 30% probability level, and showing the labelling scheme for non-H atoms.
[Figure 2] Fig. 2. View, along the b axis, of the [BPEH]nn+ organic cationic layer, showing the packing of the one-dimensional BPEH+ chains.
[Figure 3] Fig. 3. View, along the b axis, of the [(NO3)·3H2O]nn- anionic inorganic layer, showing the two-dimensional hydrogen-bonding network (dashed lines) between the nitrate ions and the water molecules. For hydrogen-bonding geometry and symmetry codes, see Table 2.
[Figure 4] Fig. 4. Perspective view of (I), showing the hydrogen-bonding network (dashed lines).
4-[2-(4-Pyridyl)ethyl]pyridinium nitrate trihydrate top
Crystal data top
C12H13N2+·NO3·3H2OF(000) = 1280
Mr = 301.30Dx = 1.322 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
a = 11.7751 (4) ÅCell parameters from 15908 reflections
b = 16.1980 (7) Åθ = 1.0–25.0°
c = 15.8787 (4) ŵ = 0.11 mm1
β = 90.175 (2)°T = 180 K
V = 3028.58 (18) Å3Block, colourless
Z = 80.46 × 0.39 × 0.12 mm
Data collection top
Nonius KappaCCD
diffractometer
5304 independent reflections
Radiation source: fine-focus sealed tube3982 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.041
Thin–slice ω and ϕ scansθmax = 25.1°, θmin = 3.6°
Absorption correction: multi-scan
(SORTAV; Blessing, 1995)
h = 1414
Tmin = 0.953, Tmax = 0.987k = 1819
21624 measured reflectionsl = 1818
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)] = 0.076Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.222H atoms treated by a mixture of independent and constrained refinement
S = 1.06 w = 1/[σ2(Fo2) + (0.1132P)2 + 1.9726P]
where P = (Fo2 + 2Fc2)/3
5304 reflections(Δ/σ)max = 0.026
423 parametersΔρmax = 0.71 e Å3
20 restraintsΔρmin = 0.30 e Å3
Crystal data top
C12H13N2+·NO3·3H2OV = 3028.58 (18) Å3
Mr = 301.30Z = 8
Monoclinic, P21/cMo Kα radiation
a = 11.7751 (4) ŵ = 0.11 mm1
b = 16.1980 (7) ÅT = 180 K
c = 15.8787 (4) Å0.46 × 0.39 × 0.12 mm
β = 90.175 (2)°
Data collection top
Nonius KappaCCD
diffractometer
5304 independent reflections
Absorption correction: multi-scan
(SORTAV; Blessing, 1995)
3982 reflections with I > 2σ(I)
Tmin = 0.953, Tmax = 0.987Rint = 0.041
21624 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.07620 restraints
wR(F2) = 0.222H atoms treated by a mixture of independent and constrained refinement
S = 1.06Δρmax = 0.71 e Å3
5304 reflectionsΔρmin = 0.30 e Å3
423 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*/Ueq
N110.25795 (16)1.01182 (13)0.86038 (13)0.0354 (5)
N120.51924 (16)1.01354 (14)0.88350 (13)0.0351 (5)
H12N0.5925 (11)1.015 (3)0.871 (2)0.089 (4)*
C110.1976 (2)1.08140 (16)0.85559 (17)0.0394 (6)
H11A0.23561.13300.85950.047*
C120.0815 (2)1.08024 (16)0.84503 (16)0.0391 (6)
H12A0.04031.13060.84190.047*
C130.0250 (2)1.00569 (16)0.83906 (15)0.0336 (6)
C140.0889 (2)0.93446 (17)0.84450 (18)0.0422 (6)
H14A0.05320.88200.84100.051*
C150.2042 (2)0.93975 (17)0.85495 (18)0.0439 (7)
H15A0.24730.89030.85840.053*
C160.1025 (2)1.00308 (18)0.83076 (16)0.0389 (6)
H16A0.12821.05020.79600.047*
H16B0.12510.95150.80190.047*
C170.1595 (2)1.00711 (19)0.91745 (16)0.0411 (6)
H17A0.13351.05710.94770.049*
H17B0.13740.95820.95100.049*
C180.2861 (2)1.00948 (16)0.90836 (14)0.0334 (6)
C190.3429 (2)1.08334 (16)0.89421 (16)0.0387 (6)
H19A0.30181.13380.89280.046*
C1100.4587 (2)1.08349 (16)0.88228 (16)0.0388 (6)
H11B0.49651.13450.87300.047*
C1110.4666 (2)0.94185 (16)0.89694 (16)0.0388 (6)
H11C0.51000.89240.89750.047*
C1120.3508 (2)0.93746 (17)0.91000 (16)0.0401 (6)
H11D0.31550.88570.92000.048*
N210.00299 (17)1.00612 (13)0.60946 (13)0.0358 (5)
H21N0.0770 (10)1.001 (2)0.617 (2)0.089 (4)*
N220.77418 (16)1.00920 (13)0.63403 (13)0.0349 (5)
C210.0523 (2)1.07773 (17)0.60263 (18)0.0439 (7)
H21A0.01071.12790.60510.053*
C220.1683 (2)1.08034 (17)0.59213 (18)0.0434 (7)
H22A0.20591.13200.58710.052*
C230.2299 (2)1.00780 (16)0.58892 (14)0.0327 (6)
C240.1705 (2)0.93431 (16)0.59563 (16)0.0398 (6)
H24A0.20980.88310.59300.048*
C250.0537 (2)0.93559 (16)0.60615 (17)0.0398 (6)
H25A0.01360.88490.61110.048*
C260.3575 (2)1.00845 (17)0.58087 (16)0.0378 (6)
H26A0.38091.05440.54370.045*
H26B0.38320.95610.55490.045*
C270.4136 (2)1.01861 (18)0.66735 (15)0.0388 (6)
H27A0.39031.07190.69250.047*
H27B0.38840.97370.70520.047*
C280.54147 (19)1.01622 (15)0.65877 (14)0.0322 (6)
C290.6045 (2)1.08762 (17)0.64825 (16)0.0405 (6)
H29A0.56851.14010.64960.049*
C2100.7195 (2)1.08194 (17)0.63581 (17)0.0405 (6)
H21B0.76191.13120.62820.049*
C2110.7141 (2)0.94015 (17)0.64531 (16)0.0395 (6)
H21C0.75240.88850.64480.047*
C2120.5986 (2)0.94157 (16)0.65767 (16)0.0373 (6)
H21D0.55810.89140.66540.045*
N310.3773 (2)0.74636 (14)0.98086 (15)0.0462 (6)
O310.4662 (2)0.74849 (15)0.94000 (13)0.0649 (6)
O320.28801 (19)0.76856 (15)0.94417 (14)0.0645 (6)
O330.3752 (2)0.72427 (14)1.05453 (14)0.0673 (7)
N410.1340 (2)0.76654 (13)0.77466 (14)0.0433 (6)
O410.1325 (2)0.76995 (14)0.69782 (13)0.0599 (6)
O420.2236 (2)0.77828 (16)0.81497 (14)0.0691 (7)
O430.04672 (18)0.74937 (14)0.81572 (13)0.0565 (6)
O5W0.4197 (2)0.7775 (2)0.70942 (17)0.0826 (9)
H5A0.365 (2)0.782 (3)0.7367 (19)0.089 (4)*
H5B0.402 (3)0.770 (3)0.6629 (12)0.089 (4)*
O6W0.1359 (2)0.7730 (2)0.98979 (15)0.0910 (10)
H6A0.128 (3)0.773 (3)0.9411 (11)0.089 (4)*
H6B0.078 (2)0.762 (3)1.010 (2)0.089 (4)*
O7W0.0855 (2)0.7533 (3)1.0474 (2)0.1004 (11)
H7A0.142 (2)0.754 (3)1.021 (2)0.089 (4)*
H7B0.104 (3)0.752 (3)1.0941 (12)0.089 (4)*
O8W0.6535 (2)0.7428 (3)1.05106 (18)0.1065 (12)
H8A0.610 (3)0.732 (3)1.0166 (19)0.089 (4)*
H8B0.7138 (18)0.747 (3)1.032 (2)0.089 (4)*
O9W0.3625 (2)0.7473 (2)0.76751 (14)0.0777 (8)
H9A0.374 (3)0.753 (3)0.8156 (12)0.089 (4)*
H9B0.4227 (19)0.748 (3)0.747 (2)0.089 (4)*
O10W0.1474 (3)0.7373 (3)0.7077 (2)0.1367 (18)
H10A0.2084 (17)0.735 (3)0.726 (2)0.089 (4)*
H10B0.104 (2)0.724 (3)0.7416 (19)0.089 (4)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N110.0241 (11)0.0431 (12)0.0389 (12)0.0009 (9)0.0022 (8)0.0013 (9)
N120.0199 (10)0.0468 (13)0.0386 (11)0.0013 (9)0.0015 (8)0.0017 (9)
C110.0281 (13)0.0392 (14)0.0510 (15)0.0033 (11)0.0002 (11)0.0033 (11)
C120.0272 (13)0.0400 (14)0.0502 (15)0.0050 (11)0.0015 (11)0.0001 (11)
C130.0227 (12)0.0462 (15)0.0318 (13)0.0013 (10)0.0029 (9)0.0011 (10)
C140.0288 (14)0.0367 (14)0.0611 (17)0.0026 (11)0.0009 (12)0.0015 (12)
C150.0286 (14)0.0401 (15)0.0630 (17)0.0052 (11)0.0032 (12)0.0027 (12)
C160.0220 (13)0.0575 (17)0.0373 (14)0.0010 (11)0.0002 (10)0.0037 (11)
C170.0213 (12)0.0656 (18)0.0363 (14)0.0013 (11)0.0008 (10)0.0017 (12)
C180.0226 (12)0.0498 (15)0.0279 (12)0.0018 (11)0.0015 (9)0.0000 (10)
C190.0286 (13)0.0412 (14)0.0463 (15)0.0077 (11)0.0019 (11)0.0032 (11)
C1100.0297 (13)0.0399 (14)0.0469 (14)0.0024 (11)0.0015 (11)0.0006 (11)
C1110.0296 (13)0.0384 (14)0.0483 (15)0.0039 (11)0.0047 (11)0.0021 (11)
C1120.0290 (14)0.0427 (15)0.0485 (15)0.0040 (11)0.0039 (11)0.0074 (12)
N210.0204 (10)0.0458 (13)0.0412 (12)0.0000 (9)0.0011 (9)0.0021 (9)
N220.0229 (10)0.0438 (12)0.0381 (11)0.0011 (9)0.0013 (8)0.0010 (9)
C210.0305 (14)0.0393 (15)0.0618 (17)0.0060 (11)0.0002 (12)0.0049 (12)
C220.0298 (14)0.0389 (15)0.0614 (17)0.0066 (11)0.0005 (12)0.0002 (12)
C230.0225 (12)0.0469 (15)0.0288 (12)0.0002 (10)0.0003 (9)0.0019 (10)
C240.0293 (13)0.0384 (14)0.0517 (15)0.0064 (11)0.0003 (11)0.0012 (11)
C250.0261 (13)0.0395 (14)0.0537 (16)0.0018 (11)0.0034 (11)0.0032 (11)
C260.0217 (12)0.0542 (16)0.0375 (14)0.0024 (11)0.0024 (10)0.0019 (11)
C270.0221 (12)0.0584 (17)0.0359 (13)0.0018 (11)0.0014 (10)0.0039 (12)
C280.0226 (12)0.0446 (14)0.0296 (12)0.0019 (10)0.0027 (9)0.0032 (10)
C290.0319 (14)0.0396 (15)0.0499 (15)0.0068 (11)0.0003 (11)0.0013 (11)
C2100.0299 (14)0.0391 (15)0.0525 (15)0.0044 (11)0.0016 (11)0.0004 (12)
C2110.0303 (14)0.0406 (15)0.0476 (15)0.0044 (11)0.0018 (11)0.0007 (11)
C2120.0272 (13)0.0385 (14)0.0460 (14)0.0013 (10)0.0003 (10)0.0003 (11)
N310.0551 (16)0.0381 (13)0.0453 (14)0.0027 (11)0.0042 (12)0.0014 (10)
O310.0562 (14)0.0898 (17)0.0486 (12)0.0092 (12)0.0078 (10)0.0011 (11)
O320.0551 (14)0.0757 (16)0.0627 (14)0.0037 (11)0.0099 (11)0.0073 (11)
O330.0774 (16)0.0737 (16)0.0507 (13)0.0016 (12)0.0021 (11)0.0221 (11)
N410.0513 (15)0.0327 (12)0.0458 (14)0.0004 (10)0.0016 (11)0.0005 (9)
O410.0702 (15)0.0680 (14)0.0415 (12)0.0095 (11)0.0003 (10)0.0122 (10)
O420.0578 (14)0.0952 (18)0.0542 (13)0.0188 (13)0.0026 (11)0.0084 (12)
O430.0457 (12)0.0730 (14)0.0509 (12)0.0023 (10)0.0129 (9)0.0037 (10)
O5W0.0406 (13)0.145 (3)0.0626 (15)0.0073 (15)0.0044 (11)0.0126 (17)
O6W0.0582 (15)0.173 (3)0.0419 (13)0.0002 (18)0.0016 (11)0.0014 (17)
O7W0.0499 (15)0.171 (3)0.0801 (19)0.0071 (18)0.0027 (13)0.040 (2)
O8W0.0484 (15)0.200 (4)0.0705 (18)0.006 (2)0.0022 (13)0.030 (2)
O9W0.0564 (15)0.134 (2)0.0428 (13)0.0021 (15)0.0028 (11)0.0067 (14)
O10W0.0437 (16)0.286 (6)0.080 (2)0.017 (2)0.0081 (14)0.041 (3)
Geometric parameters (Å, º) top
N11—C151.331 (3)C23—C241.385 (4)
N11—C111.335 (3)C23—C261.509 (3)
N12—C1111.334 (3)C24—C251.387 (4)
N12—C1101.339 (3)C24—H24A0.950
N12—H12N0.887 (10)C25—H25A0.950
C11—C121.379 (4)C26—C271.531 (4)
C11—H11A0.950C26—H26A0.990
C12—C131.382 (4)C26—H26B0.990
C12—H12A0.950C27—C281.512 (3)
C13—C141.381 (4)C27—H27A0.990
C13—C161.507 (3)C27—H27B0.990
C14—C151.371 (4)C28—C2121.384 (3)
C14—H14A0.950C28—C291.385 (4)
C15—H15A0.950C29—C2101.371 (4)
C16—C171.531 (4)C29—H29A0.950
C16—H16A0.990C210—H21B0.950
C16—H16B0.990C211—C2121.376 (3)
C17—C181.499 (3)C211—H21C0.950
C17—H17A0.990C212—H21D0.950
C17—H17B0.990N31—O331.224 (3)
C18—C191.389 (4)N31—O311.230 (3)
C18—C1121.393 (4)N31—O321.257 (3)
C19—C1101.377 (4)N41—O411.221 (3)
C19—H19A0.950N41—O421.246 (3)
C110—H11B0.950N41—O431.250 (3)
C111—C1121.382 (4)O5W—H5A0.785 (17)
C111—H11C0.950O5W—H5B0.778 (17)
C112—H11D0.950O6W—H6A0.779 (17)
N21—C251.324 (3)O6W—H6B0.776 (17)
N21—C211.335 (3)O7W—H7A0.793 (17)
N21—H21N0.883 (10)O7W—H7B0.774 (17)
N22—C2111.336 (3)O8W—H8A0.772 (17)
N22—C2101.343 (3)O8W—H8B0.775 (17)
C21—C221.378 (4)O9W—H9A0.782 (17)
C21—H21A0.950O9W—H9B0.783 (17)
C22—C231.382 (4)O10W—H10A0.778 (17)
C22—H22A0.950O10W—H10B0.771 (17)
C15—N11—C11118.9 (2)C22—C21—H21A119.3
C111—N12—C110119.4 (2)C21—C22—C23120.0 (2)
C111—N12—H12N121 (3)C21—C22—H22A120.0
C110—N12—H12N119 (3)C23—C22—H22A120.0
N11—C11—C12121.6 (2)C22—C23—C24117.6 (2)
N11—C11—H11A119.2C22—C23—C26121.4 (2)
C12—C11—H11A119.2C24—C23—C26121.0 (2)
C11—C12—C13119.9 (2)C23—C24—C25119.8 (2)
C11—C12—H12A120.1C23—C24—H24A120.1
C13—C12—H12A120.1C25—C24—H24A120.1
C14—C13—C12117.6 (2)N21—C25—C24121.2 (2)
C14—C13—C16121.7 (2)N21—C25—H25A119.4
C12—C13—C16120.7 (2)C24—C25—H25A119.4
C15—C14—C13119.7 (2)C23—C26—C27110.6 (2)
C15—C14—H14A120.1C23—C26—H26A109.5
C13—C14—H14A120.1C27—C26—H26A109.5
N11—C15—C14122.3 (2)C23—C26—H26B109.5
N11—C15—H15A118.9C27—C26—H26B109.5
C14—C15—H15A118.9H26A—C26—H26B108.1
C13—C16—C17110.7 (2)C28—C27—C26110.1 (2)
C13—C16—H16A109.5C28—C27—H27A109.6
C17—C16—H16A109.5C26—C27—H27A109.6
C13—C16—H16B109.5C28—C27—H27B109.6
C17—C16—H16B109.5C26—C27—H27B109.6
H16A—C16—H16B108.1H27A—C27—H27B108.2
C18—C17—C16110.4 (2)C212—C28—C29117.9 (2)
C18—C17—H17A109.6C212—C28—C27120.5 (2)
C16—C17—H17A109.6C29—C28—C27121.6 (2)
C18—C17—H17B109.6C210—C29—C28119.4 (2)
C16—C17—H17B109.6C210—C29—H29A120.3
H17A—C17—H17B108.1C28—C29—H29A120.3
C19—C18—C112117.4 (2)N22—C210—C29122.4 (2)
C19—C18—C17121.1 (2)N22—C210—H21B118.8
C112—C18—C17121.4 (2)C29—C210—H21B118.8
C110—C19—C18120.1 (2)N22—C211—C212122.0 (2)
C110—C19—H19A120.0N22—C211—H21C119.0
C18—C19—H19A120.0C212—C211—H21C119.0
N12—C110—C19121.6 (2)C211—C212—C28119.8 (2)
N12—C110—H11B119.2C211—C212—H21D120.1
C19—C110—H11B119.2C28—C212—H21D120.1
N12—C111—C112121.9 (2)O33—N31—O31121.9 (3)
N12—C111—H11C119.1O33—N31—O32120.8 (3)
C112—C111—H11C119.1O31—N31—O32117.3 (2)
C111—C112—C18119.6 (2)O41—N41—O42121.0 (2)
C111—C112—H11D120.2O41—N41—O43121.4 (3)
C18—C112—H11D120.2O42—N41—O43117.5 (2)
C25—N21—C21120.1 (2)H5A—O5W—H5B108 (3)
C25—N21—H21N115 (3)H6A—O6W—H6B108 (3)
C21—N21—H21N125 (3)H7A—O7W—H7B106 (2)
C211—N22—C210118.5 (2)H8A—O8W—H8B111 (3)
N21—C21—C22121.4 (2)H9A—O9W—H9B105 (2)
N21—C21—H21A119.3H10A—O10W—H10B109 (3)
C15—N11—C11—C120.1 (4)C25—N21—C21—C220.0 (4)
N11—C11—C12—C130.1 (4)N21—C21—C22—C230.3 (4)
C11—C12—C13—C140.3 (4)C21—C22—C23—C240.7 (4)
C11—C12—C13—C16177.7 (2)C21—C22—C23—C26177.6 (2)
C12—C13—C14—C150.4 (4)C22—C23—C24—C250.7 (4)
C16—C13—C14—C15177.7 (2)C26—C23—C24—C25177.6 (2)
C11—N11—C15—C140.1 (4)C21—N21—C25—C240.0 (4)
C13—C14—C15—N110.2 (4)C23—C24—C25—N210.4 (4)
C14—C13—C16—C1792.2 (3)C22—C23—C26—C2784.1 (3)
C12—C13—C16—C1785.0 (3)C24—C23—C26—C2794.2 (3)
C13—C16—C17—C18176.7 (2)C23—C26—C27—C28178.1 (2)
C16—C17—C18—C1984.4 (3)C26—C27—C28—C21285.0 (3)
C16—C17—C18—C11292.7 (3)C26—C27—C28—C2992.3 (3)
C112—C18—C19—C1100.1 (4)C212—C28—C29—C2101.1 (4)
C17—C18—C19—C110177.1 (2)C27—C28—C29—C210176.2 (2)
C111—N12—C110—C190.3 (4)C211—N22—C210—C290.4 (4)
C18—C19—C110—N120.3 (4)C28—C29—C210—N220.5 (4)
C110—N12—C111—C1120.2 (4)C210—N22—C211—C2120.7 (4)
N12—C111—C112—C180.7 (4)N22—C211—C212—C280.1 (4)
C19—C18—C112—C1110.6 (4)C29—C28—C212—C2110.8 (4)
C17—C18—C112—C111176.6 (2)C27—C28—C212—C211176.5 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N12—H12N···N11i0.88 (1)1.77 (1)2.650 (3)171 (4)
N21—H21N···N22ii0.88 (1)1.78 (1)2.654 (3)171 (4)
O5W—H5A···O420.78 (2)2.08 (2)2.858 (3)172 (4)
O5W—H5B···O8Wiii0.78 (2)1.90 (2)2.676 (4)176 (4)
O6W—H6A···O430.78 (2)2.24 (2)2.979 (3)158 (4)
O6W—H6A···O420.78 (2)2.30 (2)2.966 (3)144 (3)
O6W—H6B···O7W0.78 (2)2.02 (2)2.785 (4)169 (4)
O7W—H7A···O320.78 (2)2.11 (2)2.900 (4)173 (4)
O7W—H7B···O10Wiv0.77 (2)1.88 (2)2.654 (5)174 (5)
O8W—H8A···O310.77 (2)2.10 (2)2.829 (4)157 (4)
O8W—H8B···O6Wii0.78 (2)1.94 (2)2.705 (4)172 (4)
O9W—H9A···O310.78 (2)2.26 (2)3.003 (3)160 (4)
O9W—H9A···O320.78 (2)2.29 (2)2.957 (3)144 (3)
O9W—H9B···O5Wii0.78 (2)2.00 (2)2.767 (3)165 (4)
O10W—H10A···O9W0.78 (2)1.94 (2)2.713 (4)172 (4)
O10W—H10B···O430.77 (2)2.17 (3)2.860 (4)150 (4)
Symmetry codes: (i) x+1, y, z; (ii) x1, y, z; (iii) x+1, y+3/2, z1/2; (iv) x, y+3/2, z+1/2.

Experimental details

Crystal data
Chemical formulaC12H13N2+·NO3·3H2O
Mr301.30
Crystal system, space groupMonoclinic, P21/c
Temperature (K)180
a, b, c (Å)11.7751 (4), 16.1980 (7), 15.8787 (4)
β (°) 90.175 (2)
V3)3028.58 (18)
Z8
Radiation typeMo Kα
µ (mm1)0.11
Crystal size (mm)0.46 × 0.39 × 0.12
Data collection
DiffractometerNonius KappaCCD
diffractometer
Absorption correctionMulti-scan
(SORTAV; Blessing, 1995)
Tmin, Tmax0.953, 0.987
No. of measured, independent and
observed [I > 2σ(I)] reflections
21624, 5304, 3982
Rint0.041
(sin θ/λ)max1)0.596
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.076, 0.222, 1.06
No. of reflections5304
No. of parameters423
No. of restraints20
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)0.71, 0.30

Computer programs: COLLECT (Nonius, 1998), HKL SCALEPACK (Otwinowski & Minor, 1997), HKL DENZO (Otwinowski & Minor, 1997) and SCALEPACK, SIR92 (Altomare et al., 1994), SHELXTL (Bruker, 2001), SHELXTL.

Selected geometric parameters (Å, º) top
N31—O331.224 (3)N41—O411.221 (3)
N31—O311.230 (3)N41—O421.246 (3)
N31—O321.257 (3)N41—O431.250 (3)
O33—N31—O31121.9 (3)O41—N41—O42121.0 (2)
O33—N31—O32120.8 (3)O41—N41—O43121.4 (3)
O31—N31—O32117.3 (2)O42—N41—O43117.5 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N12—H12N···N11i0.88 (1)1.77 (1)2.650 (3)171 (4)
N21—H21N···N22ii0.88 (1)1.78 (1)2.654 (3)171 (4)
O5W—H5A···O420.78 (2)2.08 (2)2.858 (3)172 (4)
O5W—H5B···O8Wiii0.78 (2)1.90 (2)2.676 (4)176 (4)
O6W—H6A···O430.78 (2)2.24 (2)2.979 (3)158 (4)
O6W—H6A···O420.78 (2)2.30 (2)2.966 (3)144 (3)
O6W—H6B···O7W0.78 (2)2.02 (2)2.785 (4)169 (4)
O7W—H7A···O320.78 (2)2.11 (2)2.900 (4)173 (4)
O7W—H7B···O10Wiv0.77 (2)1.88 (2)2.654 (5)174 (5)
O8W—H8A···O310.77 (2)2.10 (2)2.829 (4)157 (4)
O8W—H8B···O6Wii0.78 (2)1.94 (2)2.705 (4)172 (4)
O9W—H9A···O310.78 (2)2.26 (2)3.003 (3)160 (4)
O9W—H9A···O320.78 (2)2.29 (2)2.957 (3)144 (3)
O9W—H9B···O5Wii0.78 (2)2.00 (2)2.767 (3)165 (4)
O10W—H10A···O9W0.78 (2)1.94 (2)2.713 (4)172 (4)
O10W—H10B···O430.77 (2)2.17 (3)2.860 (4)150 (4)
Symmetry codes: (i) x+1, y, z; (ii) x1, y, z; (iii) x+1, y+3/2, z1/2; (iv) x, y+3/2, z+1/2.
 

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