N,N'-Bis­[2-(2-pyridyl)­methyl]­pyridine-2,6-dicarbox­amide hemihydrate

The structure of the title pentadentate ligand as its hemi­hydrate, C₁₉H₁₇N₅O₂·0.5H₂O, is different from the structure of a similar tridentate ligand reported previously [Qi et al. (2001). Acta Cryst. E57, o749-o750; Yang et al. (2001). Acta Cryst. E57, o1161-o1162]. The two pyridine side arms are not in the same plane, owing to their rotation around an axis between the pyridine ring and the methyl­ene group. There is an intermolecular hydrogen bond between the ligand and the disordered lattice water mol­ecule.

Key indicators

• Single-crystal X-ray study
• T = 294 K
• Mean [sigma](C-C) = 0.005 Å
• Disorder in solvent or counterion
• R factor = 0.055
• wR factor = 0.137
• Data-to-parameter ratio = 16.9

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry


 Alert Level C:



DIFMX_01  Alert C The maximum difference density is > 0.1*ZMAX*0.75
          _refine_diff_density_max given =      0.643
          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.

PLAT_302  Alert C Anion/Solvent Disorder .......................      50.00 Perc.


 0 Alert Level A = Potentially serious problem

 0 Alert Level B = Potential problem

 3 Alert Level C = Please check

---

Computing details

Data collection: SMART (Bruker, 1995); cell refinement: SMART; data reduction: SHELXTL-NT (Bruker, 1995); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL-NT; software used to prepare material for publication: SHELXTL-NT.

N,N'-Bis[2-(2-pyridyl)methyl]pyridine-2,6-dicarboxamide hemihydrate

Crystal data

C19H17N5O2·0.5H2O	F(000) = 1496
Mr = 356.38	Dx = 1.319 Mg m^−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
a = 17.784 (3) Å	Cell parameters from 2885 reflections
b = 17.611 (3) Å	θ = 1–27.5°
c = 14.217 (2) Å	µ = 0.09 mm^−1
β = 126.310 (3)°	T = 294 K
V = 3588.2 (9) Å^3	Prism, colorless
Z = 8	0.34 × 0.28 × 0.24 mm

Data collection

Bruker SMART CCD area-detector diffractometer	4127 independent reflections
Radiation source: fine-focus sealed tube	1561 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.053
φ and ω scans	θmax = 27.6°, θmin = 2.3°
Absorption correction: empirical (using intensity measurements) (SADABS; Sheldrick, 1996)	h = −12→23
Tmin = 0.970, Tmax = 0.978	k = −22→22
12125 measured reflections	l = −18→16

Refinement

Refinement on F^2	0 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.055	H-atom parameters constrained
wR(F^2) = 0.137	w = 1/[σ^2(Fo^2) + (0.05P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 1.05	(Δ/σ)max < 0.001
4127 reflections	Δρmax = 0.64 e Å^−3
244 parameters	Δρmin = −0.23 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	Occ. (<1)
O1	−0.17747 (14)	0.54518 (10)	−0.06191 (16)	0.0755 (6)
O2	0.23911 (14)	0.36132 (11)	0.37372 (17)	0.0836 (6)
N1	0.04155 (15)	0.47455 (11)	0.17237 (17)	0.0509 (5)
N2	−0.05078 (15)	0.60421 (11)	0.09148 (18)	0.0589 (6)
H2A	0.0057	0.5982	0.1523	0.071*
N3	−0.14649 (15)	0.65671 (11)	0.17812 (18)	0.0616 (6)
N4	0.21620 (15)	0.48847 (12)	0.36406 (17)	0.0605 (6)
H4B	0.1757	0.5242	0.3280	0.073*
N5	0.43655 (18)	0.58866 (13)	0.50656 (19)	0.0727 (7)
C1	−0.0983 (2)	0.54326 (16)	0.0289 (2)	0.0541 (7)
C2	−0.04630 (18)	0.46983 (15)	0.0776 (2)	0.0506 (6)
C3	−0.0898 (2)	0.40161 (16)	0.0266 (2)	0.0648 (7)
H3A	−0.1517	0.4002	−0.0387	0.078*
C4	−0.0396 (2)	0.33577 (17)	0.0746 (3)	0.0760 (9)
H4A	−0.0671	0.2891	0.0413	0.091*
C5	0.0518 (2)	0.33920 (15)	0.1724 (3)	0.0691 (8)
H5A	0.0866	0.2951	0.2061	0.083*
C6	0.09060 (19)	0.41007 (15)	0.2196 (2)	0.0538 (7)
C7	−0.08897 (19)	0.67979 (14)	0.0627 (2)	0.0623 (7)
H7A	−0.1408	0.6811	−0.0196	0.075*
H7B	−0.0416	0.7144	0.0744	0.075*
C8	−0.12252 (16)	0.70828 (14)	0.13134 (19)	0.0498 (6)
C9	−0.1300 (2)	0.78437 (15)	0.1417 (2)	0.0700 (8)
H9A	−0.1123	0.8188	0.1086	0.084*
C10	−0.1633 (2)	0.80942 (18)	0.2001 (3)	0.0901 (10)
H10A	−0.1681	0.8613	0.2078	0.108*
C11	−0.1898 (2)	0.7588 (2)	0.2479 (3)	0.0805 (9)
H11A	−0.2138	0.7773	0.2910	0.097*
C12	−0.1798 (2)	0.68350 (18)	0.2353 (2)	0.0744 (8)
H12A	−0.1998	0.6462	0.2687	0.089*
C13	0.1887 (2)	0.41797 (17)	0.3266 (2)	0.0585 (7)
C14	0.30969 (18)	0.50936 (16)	0.4615 (2)	0.0657 (8)
H14A	0.3422	0.4643	0.5071	0.079*
H14B	0.3059	0.5444	0.5113	0.079*
C15	0.36524 (18)	0.54543 (14)	0.4256 (2)	0.0559 (7)
C16	0.3464 (2)	0.53489 (16)	0.3180 (2)	0.0709 (8)
H16A	0.2971	0.5040	0.2630	0.085*
C17	0.4007 (2)	0.57019 (18)	0.2920 (3)	0.0821 (9)
H17A	0.3880	0.5638	0.2189	0.099*
C18	0.4732 (2)	0.61461 (17)	0.3734 (3)	0.0799 (9)
H18A	0.5106	0.6395	0.3575	0.096*
C19	0.4891 (2)	0.62146 (17)	0.4794 (3)	0.0846 (9)
H19A	0.5395	0.6507	0.5362	0.102*
O1W	0.3046 (4)	0.2906 (2)	0.5826 (4)	0.146 (2)	0.50
H1WA	0.2693	0.2790	0.5106	0.175*	0.50
H1WB	0.3609	0.2882	0.6059	0.175*	0.50

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0669 (13)	0.0878 (14)	0.0575 (12)	−0.0008 (12)	0.0289 (11)	−0.0050 (11)
O2	0.0887 (15)	0.0671 (13)	0.0920 (15)	0.0298 (12)	0.0519 (13)	0.0134 (11)
N1	0.0594 (14)	0.0520 (14)	0.0548 (13)	0.0024 (12)	0.0412 (13)	−0.0046 (11)
N2	0.0576 (13)	0.0552 (14)	0.0568 (13)	0.0100 (13)	0.0300 (12)	−0.0032 (12)
N3	0.0763 (16)	0.0560 (14)	0.0634 (14)	−0.0035 (13)	0.0474 (14)	−0.0039 (11)
N4	0.0599 (15)	0.0574 (14)	0.0615 (14)	0.0076 (13)	0.0345 (13)	0.0020 (12)
N5	0.0742 (16)	0.0769 (17)	0.0649 (16)	−0.0034 (15)	0.0400 (15)	−0.0123 (13)
C1	0.0560 (17)	0.0664 (19)	0.0474 (16)	0.0000 (17)	0.0347 (15)	−0.0042 (15)
C2	0.0582 (17)	0.0566 (17)	0.0499 (15)	−0.0021 (16)	0.0392 (15)	−0.0094 (14)
C3	0.0730 (19)	0.069 (2)	0.0637 (18)	−0.0075 (18)	0.0465 (16)	−0.0156 (16)
C4	0.093 (2)	0.060 (2)	0.086 (2)	−0.017 (2)	0.060 (2)	−0.0223 (18)
C5	0.094 (2)	0.0513 (18)	0.083 (2)	0.0025 (18)	0.064 (2)	−0.0033 (16)
C6	0.0681 (19)	0.0525 (17)	0.0601 (17)	0.0039 (16)	0.0486 (16)	−0.0023 (14)
C7	0.0679 (18)	0.0581 (17)	0.0628 (17)	0.0057 (15)	0.0397 (16)	0.0070 (14)
C8	0.0488 (15)	0.0471 (16)	0.0465 (15)	0.0027 (13)	0.0244 (14)	0.0020 (12)
C9	0.090 (2)	0.0499 (18)	0.073 (2)	0.0129 (17)	0.0496 (19)	0.0073 (15)
C10	0.106 (3)	0.059 (2)	0.095 (3)	0.023 (2)	0.054 (2)	−0.0022 (18)
C11	0.076 (2)	0.091 (3)	0.075 (2)	0.017 (2)	0.0450 (19)	−0.0141 (19)
C12	0.079 (2)	0.084 (2)	0.068 (2)	−0.0105 (19)	0.0482 (18)	−0.0067 (17)
C13	0.070 (2)	0.0595 (19)	0.0616 (19)	0.0088 (18)	0.0477 (18)	0.0030 (16)
C14	0.0621 (18)	0.0778 (19)	0.0530 (17)	0.0046 (16)	0.0318 (17)	−0.0011 (14)
C15	0.0551 (16)	0.0573 (17)	0.0523 (17)	0.0062 (15)	0.0302 (15)	−0.0029 (14)
C16	0.0721 (19)	0.080 (2)	0.0592 (18)	−0.0075 (18)	0.0378 (17)	−0.0118 (16)
C17	0.091 (2)	0.098 (2)	0.074 (2)	−0.005 (2)	0.058 (2)	−0.0059 (19)
C18	0.084 (2)	0.077 (2)	0.093 (2)	−0.005 (2)	0.061 (2)	−0.0030 (19)
C19	0.078 (2)	0.080 (2)	0.091 (3)	−0.0187 (19)	0.047 (2)	−0.0209 (18)
O1W	0.182 (5)	0.104 (4)	0.101 (3)	0.014 (4)	0.055 (4)	0.018 (3)

Geometric parameters (Å, º)

O1—C1	1.223 (3)	C7—H7A	0.9700
O2—C13	1.239 (3)	C7—H7B	0.9700
N1—C2	1.331 (3)	C8—C9	1.363 (3)
N1—C6	1.345 (3)	C9—C10	1.347 (4)
N2—C1	1.330 (3)	C9—H9A	0.9300
N2—C7	1.439 (3)	C10—C11	1.362 (4)
N2—H2A	0.8600	C10—H10A	0.9300
N3—C8	1.336 (3)	C11—C12	1.364 (4)
N3—C12	1.343 (3)	C11—H11A	0.9885
N4—C13	1.325 (3)	C12—H12A	0.9922
N4—C14	1.446 (3)	C14—C15	1.496 (3)
N4—H4B	0.8600	C14—H14A	0.9700
N5—C19	1.335 (3)	C14—H14B	0.9700
N5—C15	1.336 (3)	C15—C16	1.371 (3)
C1—C2	1.500 (3)	C16—C17	1.371 (4)
C2—C3	1.380 (3)	C16—H16A	0.9300
C3—C4	1.373 (3)	C17—C18	1.359 (4)
C3—H3A	0.9300	C17—H17A	0.9300
C4—C5	1.379 (4)	C18—C19	1.364 (4)
C4—H4A	0.9300	C18—H18A	0.9300
C5—C6	1.392 (3)	C19—H19A	0.9300
C5—H5A	0.9300	O1W—H1WA	0.8500
C6—C13	1.495 (3)	O1W—H1WB	0.8499
C7—C8	1.500 (3)
C2—N1—C6	118.6 (2)	C10—C9—H9A	120.2
C1—N2—C7	123.4 (2)	C8—C9—H9A	120.2
C1—N2—H2A	118.3	C9—C10—C11	120.0 (3)
C7—N2—H2A	118.3	C9—C10—H10A	120.0
C8—N3—C12	116.6 (2)	C11—C10—H10A	120.0
C13—N4—C14	124.4 (2)	C10—C11—C12	117.4 (3)
C13—N4—H4B	117.8	C10—C11—H11A	120.0
C14—N4—H4B	117.8	C12—C11—H11A	122.6
C19—N5—C15	117.9 (2)	N3—C12—C11	124.0 (3)
O1—C1—N2	124.2 (3)	N3—C12—H12A	117.9
O1—C1—C2	121.4 (3)	C11—C12—H12A	118.1
N2—C1—C2	114.4 (2)	O2—C13—N4	124.1 (3)
N1—C2—C3	122.9 (3)	O2—C13—C6	120.7 (3)
N1—C2—C1	116.6 (2)	N4—C13—C6	115.3 (3)
C3—C2—C1	120.5 (3)	N4—C14—C15	113.4 (2)
C4—C3—C2	118.5 (3)	N4—C14—H14A	108.9
C4—C3—H3A	120.7	C15—C14—H14A	108.9
C2—C3—H3A	120.7	N4—C14—H14B	108.9
C3—C4—C5	119.7 (3)	C15—C14—H14B	108.9
C3—C4—H4A	120.2	H14A—C14—H14B	107.7
C5—C4—H4A	120.2	N5—C15—C16	121.2 (3)
C4—C5—C6	118.5 (3)	N5—C15—C14	115.5 (2)
C4—C5—H5A	120.7	C16—C15—C14	123.3 (3)
C6—C5—H5A	120.7	C15—C16—C17	119.6 (3)
N1—C6—C5	121.8 (3)	C15—C16—H16A	120.2
N1—C6—C13	116.8 (2)	C17—C16—H16A	120.2
C5—C6—C13	121.4 (3)	C18—C17—C16	119.7 (3)
N2—C7—C8	115.2 (2)	C18—C17—H17A	120.2
N2—C7—H7A	108.5	C16—C17—H17A	120.2
C8—C7—H7A	108.5	C17—C18—C19	117.6 (3)
N2—C7—H7B	108.5	C17—C18—H18A	121.2
C8—C7—H7B	108.5	C19—C18—H18A	121.2
H7A—C7—H7B	107.5	N5—C19—C18	123.9 (3)
N3—C8—C9	122.3 (2)	N5—C19—H19A	118.0
N3—C8—C7	117.6 (2)	C18—C19—H19A	118.0
C9—C8—C7	120.1 (2)	H1WA—O1W—H1WB	108.5
C10—C9—C8	119.7 (3)
C7—N2—C1—O1	3.3 (4)	C7—C8—C9—C10	177.7 (3)
C7—N2—C1—C2	−177.6 (2)	C8—C9—C10—C11	−0.4 (5)
C6—N1—C2—C3	1.1 (3)	C9—C10—C11—C12	0.9 (5)
C6—N1—C2—C1	179.42 (19)	C8—N3—C12—C11	−0.2 (4)
O1—C1—C2—N1	175.6 (2)	C10—C11—C12—N3	−0.6 (5)
N2—C1—C2—N1	−3.5 (3)	C14—N4—C13—O2	3.0 (4)
O1—C1—C2—C3	−6.0 (3)	C14—N4—C13—C6	−176.2 (2)
N2—C1—C2—C3	174.9 (2)	N1—C6—C13—O2	−178.4 (2)
N1—C2—C3—C4	−1.3 (4)	C5—C6—C13—O2	2.4 (4)
C1—C2—C3—C4	−179.6 (2)	N1—C6—C13—N4	0.9 (3)
C2—C3—C4—C5	0.8 (4)	C5—C6—C13—N4	−178.3 (2)
C3—C4—C5—C6	−0.2 (4)	C13—N4—C14—C15	105.1 (3)
C2—N1—C6—C5	−0.3 (3)	C19—N5—C15—C16	0.0 (4)
C2—N1—C6—C13	−179.52 (19)	C19—N5—C15—C14	179.2 (2)
C4—C5—C6—N1	−0.1 (4)	N4—C14—C15—N5	157.6 (2)
C4—C5—C6—C13	179.0 (2)	N4—C14—C15—C16	−23.2 (4)
C1—N2—C7—C8	99.9 (3)	N5—C15—C16—C17	−1.0 (4)
C12—N3—C8—C9	0.8 (4)	C14—C15—C16—C17	179.9 (2)
C12—N3—C8—C7	−177.4 (2)	C15—C16—C17—C18	0.7 (4)
N2—C7—C8—N3	−23.9 (3)	C16—C17—C18—C19	0.6 (4)
N2—C7—C8—C9	157.8 (2)	C15—N5—C19—C18	1.3 (4)
N3—C8—C9—C10	−0.5 (4)	C17—C18—C19—N5	−1.6 (5)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2A···N3^i	0.86	2.45	3.207 (3)	147
N4—H4B···N3^i	0.86	2.38	3.130 (3)	146
O1W—H1WA···O1W^ii	0.85	1.71	2.435 (9)	142
O1W—H1WA···O2	0.85	2.22	2.762 (5)	121

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