A new zinc(II) complex with a peptide ligand: aqua{N,N-bis­[2-(2-pyridyl)­methyl]­pyridine-2,6-dicarbox­amide}di­chloro­zinc(II)

The title compound, [ZnCl₂(C₁₉H₁₇N₅O₂)(H₂O)], was prepared from the peptide ligand N,N-bis­[2-(2-pyridyl)­methyl]­pyridine-2,6-dicarbox­amide and zinc chloride. The Zn atom exits in a tetrahedral geometry and is coordinated by a pyridine N atom of the ligand, two chloride ions and one water O atom. The ligand coordinates to the zinc ion in a monodentate fashion.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.008 Å
• R factor = 0.054
• wR factor = 0.124
• Data-to-parameter ratio = 13.6

checkCIF/PLATON results

No syntax errors found



Alert level C
ABSTM02_ALERT_3_C  The ratio of expected to reported Tmax/Tmin(RR') is < 0.90
            Tmin and Tmax reported:      0.576     0.816
            Tmin' and Tmax expected:      0.721     0.816
            RR' =      0.799
            Please check that your absorption correction is appropriate.
PLAT061_ALERT_3_C Tmax/Tmin Range Test RR' too Large .............       0.79
PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given .......          ?
PLAT150_ALERT_1_C Volume as Calculated Differs from that Given ...    2108.50 Ang-3
PLAT341_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...          8

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   5 ALERT level C = Check and explain
   0 ALERT level G = General alerts; check

   1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   0 ALERT type 2 Indicator that the structure model may be wrong or deficient
   3 ALERT type 3 Indicator that the structure quality may be low
   1 ALERT type 4 Improvement, methodology, query or suggestion

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Computing details

Data collection: SMART (Bruker, 1998); cell refinement: SMART; data reduction: SAINT (Bruker, 1998); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1998); software used to prepare material for publication: SHELXTL.

aqua{N,N-bis[2-(2-pyridyl)methyl]pyridine-2,6-dicarboxamide}dichlorozinc(II)

Crystal data

[ZnCl2(C19H17N5O2)(H2O)]	F(000) = 1024
Mr = 501.66	Dx = 1.580 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
a = 9.210 (5) Å	Cell parameters from 770 reflections
b = 18.394 (10) Å	θ = 2.6–24.2°
c = 13.215 (7) Å	µ = 1.45 mm^−1
β = 109.657 (8)°	T = 293 K
V = 2108.5 (19) Å^3	Block, colorless
Z = 4	0.22 × 0.20 × 0.14 mm

Data collection

Bruker SMART CCD area-detector diffractometer	3693 independent reflections
Radiation source: fine-focus sealed tube	2504 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.066
φ and ω scans	θmax = 25.0°, θmin = 2.4°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −10→10
Tmin = 0.576, Tmax = 0.816	k = −21→12
10650 measured reflections	l = −14→15

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.054	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.125	H-atom parameters constrained
S = 1.03	w = 1/[σ^2(Fo^2) + (0.0563P)^2] where P = (Fo^2 + 2Fc^2)/3
3693 reflections	(Δ/σ)max = 0.004
271 parameters	Δρmax = 0.63 e Å^−3
3 restraints	Δρmin = −0.41 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
Zn1	0.28776 (7)	0.17492 (3)	0.59902 (4)	0.03546 (19)
Cl1	0.30474 (15)	0.29419 (7)	0.56252 (10)	0.0445 (3)
Cl2	0.34111 (16)	0.15062 (8)	0.77262 (10)	0.0520 (4)
O1	0.4405 (4)	0.1193 (2)	0.5529 (3)	0.0532 (10)
H1A	0.4046	0.1113	0.4881	0.064*
H1B	0.5183	0.1468	0.5781	0.064*
O2	0.3397 (4)	0.07915 (19)	0.3446 (3)	0.0549 (10)
O3	0.0035 (4)	0.03746 (18)	−0.2154 (3)	0.0414 (8)
N1	0.0816 (4)	0.13062 (18)	0.5047 (3)	0.0276 (8)
N2	0.1244 (4)	0.1398 (2)	0.2472 (3)	0.0339 (9)
H2A	0.0584	0.1466	0.1841	0.041*
N3	0.1368 (4)	0.07925 (18)	0.0636 (3)	0.0275 (8)
N4	−0.0817 (4)	0.1207 (2)	−0.1235 (3)	0.0357 (9)
H4A	−0.0650	0.1428	−0.0633	0.043*
N5	−0.2925 (5)	0.1971 (2)	−0.3878 (4)	0.0451 (11)
C1	0.0030 (5)	0.0942 (2)	0.5604 (4)	0.0353 (11)
H1	0.0469	0.0901	0.6346	0.042*
C2	−0.1392 (6)	0.0634 (3)	0.5097 (4)	0.0450 (13)
H2	−0.1920	0.0400	0.5493	0.054*
C3	−0.2022 (6)	0.0676 (3)	0.3995 (5)	0.0559 (15)
H3	−0.2972	0.0464	0.3635	0.067*
C4	−0.1227 (6)	0.1037 (3)	0.3435 (4)	0.0467 (13)
H4	−0.1640	0.1068	0.2690	0.056*
C5	0.0181 (5)	0.1354 (2)	0.3973 (3)	0.0290 (10)
C6	0.1041 (6)	0.1788 (2)	0.3379 (4)	0.0345 (11)
H6A	0.0481	0.2235	0.3117	0.041*
H6B	0.2047	0.1918	0.3878	0.041*
C7	0.2407 (5)	0.0944 (2)	0.2583 (4)	0.0331 (11)
C8	0.2470 (5)	0.0607 (2)	0.1548 (3)	0.0277 (10)
C9	0.3658 (5)	0.0132 (2)	0.1601 (4)	0.0352 (11)
H9	0.4416	0.0024	0.2253	0.042*
C10	0.3682 (6)	−0.0179 (3)	0.0650 (4)	0.0410 (12)
H10	0.4453	−0.0507	0.0657	0.049*
C11	0.2555 (6)	0.0003 (2)	−0.0306 (4)	0.0389 (12)
H11	0.2559	−0.0194	−0.0953	0.047*
C12	0.1416 (5)	0.0489 (2)	−0.0276 (4)	0.0289 (10)
C13	0.0163 (5)	0.0682 (2)	−0.1307 (4)	0.0303 (10)
C14	−0.2146 (5)	0.1406 (3)	−0.2149 (4)	0.0380 (11)
H14A	−0.2911	0.1624	−0.1888	0.046*
H14B	−0.2592	0.0967	−0.2536	0.046*
C15	−0.1810 (5)	0.1925 (2)	−0.2922 (4)	0.0322 (11)
C16	−0.0457 (6)	0.2322 (3)	−0.2691 (4)	0.0453 (13)
H16	0.0300	0.2286	−0.2018	0.054*
C17	−0.0239 (8)	0.2768 (3)	−0.3465 (6)	0.0618 (18)
H17	0.0665	0.3036	−0.3321	0.074*
C18	−0.1368 (9)	0.2812 (3)	−0.4445 (6)	0.0664 (19)
H18	−0.1244	0.3107	−0.4982	0.080*
C19	−0.2703 (8)	0.2411 (3)	−0.4627 (5)	0.0630 (17)
H19	−0.3477	0.2447	−0.5293	0.076*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Zn1	0.0357 (3)	0.0427 (4)	0.0239 (3)	−0.0028 (3)	0.0047 (2)	−0.0012 (2)
Cl1	0.0509 (8)	0.0457 (8)	0.0346 (7)	−0.0136 (6)	0.0112 (6)	0.0001 (5)
Cl2	0.0503 (8)	0.0722 (10)	0.0267 (7)	−0.0006 (7)	0.0043 (6)	0.0073 (6)
O1	0.037 (2)	0.083 (3)	0.031 (2)	0.0084 (18)	0.0014 (16)	−0.0171 (18)
O2	0.054 (2)	0.073 (3)	0.026 (2)	0.0229 (19)	−0.0018 (18)	−0.0015 (17)
O3	0.053 (2)	0.049 (2)	0.0248 (19)	−0.0024 (16)	0.0170 (16)	−0.0038 (15)
N1	0.033 (2)	0.027 (2)	0.023 (2)	0.0015 (16)	0.0092 (17)	−0.0012 (15)
N2	0.041 (2)	0.042 (2)	0.017 (2)	0.0027 (19)	0.0077 (17)	0.0004 (17)
N3	0.029 (2)	0.030 (2)	0.026 (2)	−0.0052 (15)	0.0126 (17)	−0.0002 (15)
N4	0.038 (2)	0.049 (3)	0.018 (2)	0.0050 (19)	0.0064 (17)	0.0003 (17)
N5	0.039 (3)	0.056 (3)	0.037 (3)	0.012 (2)	0.008 (2)	0.004 (2)
C1	0.039 (3)	0.035 (3)	0.034 (3)	0.003 (2)	0.015 (2)	−0.004 (2)
C2	0.046 (3)	0.041 (3)	0.057 (4)	−0.004 (2)	0.029 (3)	−0.008 (2)
C3	0.033 (3)	0.077 (4)	0.054 (4)	−0.013 (3)	0.009 (3)	−0.018 (3)
C4	0.036 (3)	0.062 (4)	0.036 (3)	−0.002 (3)	0.004 (2)	−0.006 (2)
C5	0.027 (2)	0.032 (3)	0.024 (2)	0.006 (2)	0.002 (2)	−0.0045 (19)
C6	0.043 (3)	0.036 (3)	0.021 (3)	0.004 (2)	0.006 (2)	0.0010 (19)
C7	0.034 (3)	0.034 (3)	0.027 (3)	−0.002 (2)	0.004 (2)	0.005 (2)
C8	0.030 (3)	0.029 (3)	0.023 (2)	−0.0059 (19)	0.008 (2)	0.0041 (18)
C9	0.028 (3)	0.042 (3)	0.033 (3)	−0.001 (2)	0.007 (2)	0.008 (2)
C10	0.035 (3)	0.046 (3)	0.046 (3)	0.010 (2)	0.018 (2)	0.007 (2)
C11	0.046 (3)	0.045 (3)	0.031 (3)	0.001 (2)	0.020 (2)	0.000 (2)
C12	0.031 (3)	0.028 (3)	0.029 (3)	−0.0063 (19)	0.011 (2)	0.0009 (19)
C13	0.035 (3)	0.036 (3)	0.023 (3)	−0.006 (2)	0.015 (2)	0.003 (2)
C14	0.031 (3)	0.052 (3)	0.029 (3)	0.000 (2)	0.007 (2)	0.003 (2)
C15	0.032 (3)	0.037 (3)	0.027 (3)	0.011 (2)	0.008 (2)	−0.0008 (19)
C16	0.045 (3)	0.051 (3)	0.039 (3)	−0.003 (3)	0.014 (3)	−0.006 (2)
C17	0.067 (4)	0.051 (4)	0.085 (5)	−0.003 (3)	0.050 (4)	0.001 (3)
C18	0.095 (6)	0.053 (4)	0.070 (5)	0.032 (4)	0.053 (5)	0.025 (3)
C19	0.076 (5)	0.077 (5)	0.032 (3)	0.033 (4)	0.014 (3)	0.020 (3)

Geometric parameters (Å, º)

Zn1—O1	1.994 (3)	C4—C5	1.381 (6)
Zn1—N1	2.057 (4)	C4—H4	0.9300
Zn1—Cl2	2.2239 (18)	C5—C6	1.516 (6)
Zn1—Cl1	2.2629 (17)	C6—H6A	0.9700
O1—H1A	0.8200	C6—H6B	0.9700
O1—H1B	0.8499	C7—C8	1.520 (6)
O2—C7	1.229 (5)	C8—C9	1.383 (6)
O3—C13	1.224 (5)	C9—C10	1.388 (7)
N1—C5	1.343 (5)	C9—H9	0.9300
N1—C1	1.370 (6)	C10—C11	1.379 (7)
N2—C7	1.327 (6)	C10—H10	0.9300
N2—C6	1.461 (5)	C11—C12	1.388 (6)
N2—H2A	0.8600	C11—H11	0.9300
N3—C8	1.334 (5)	C12—C13	1.503 (6)
N3—C12	1.342 (6)	C14—C15	1.504 (6)
N4—C13	1.346 (6)	C14—H14A	0.9700
N4—C14	1.448 (5)	C14—H14B	0.9700
N4—H4A	0.8600	C15—C16	1.387 (7)
N5—C15	1.336 (6)	C16—C17	1.378 (8)
N5—C19	1.347 (7)	C16—H16	0.9300
C1—C2	1.377 (7)	C17—C18	1.364 (9)
C1—H1	0.9300	C17—H17	0.9300
C2—C3	1.376 (7)	C18—C19	1.384 (9)
C2—H2	0.9300	C18—H18	0.9300
C3—C4	1.375 (8)	C19—H19	0.9300
C3—H3	0.9300
O1—Zn1—N1	102.31 (14)	O2—C7—C8	120.0 (4)
O1—Zn1—Cl2	106.17 (11)	N2—C7—C8	115.5 (4)
N1—Zn1—Cl2	112.60 (11)	N3—C8—C9	123.7 (4)
O1—Zn1—Cl1	109.04 (12)	N3—C8—C7	117.5 (4)
N1—Zn1—Cl1	111.76 (10)	C9—C8—C7	118.7 (4)
Cl2—Zn1—Cl1	114.06 (5)	C8—C9—C10	117.9 (4)
Zn1—O1—H1A	109.4	C8—C9—H9	121.0
Zn1—O1—H1B	99.4	C10—C9—H9	121.0
H1A—O1—H1B	120.3	C11—C10—C9	119.5 (5)
C5—N1—C1	118.6 (4)	C11—C10—H10	120.2
C5—N1—Zn1	126.8 (3)	C9—C10—H10	120.2
C1—N1—Zn1	114.5 (3)	C10—C11—C12	118.2 (5)
C7—N2—C6	122.6 (4)	C10—C11—H11	120.9
C7—N2—H2A	118.7	C12—C11—H11	120.9
C6—N2—H2A	118.7	N3—C12—C11	123.2 (4)
C8—N3—C12	117.4 (4)	N3—C12—C13	117.9 (4)
C13—N4—C14	121.3 (4)	C11—C12—C13	118.9 (4)
C13—N4—H4A	119.3	O3—C13—N4	122.4 (4)
C14—N4—H4A	119.3	O3—C13—C12	121.9 (4)
C15—N5—C19	118.3 (5)	N4—C13—C12	115.7 (4)
N1—C1—C2	121.9 (5)	N4—C14—C15	114.7 (4)
N1—C1—H1	119.0	N4—C14—H14A	108.6
C2—C1—H1	119.0	C15—C14—H14A	108.6
C3—C2—C1	119.0 (5)	N4—C14—H14B	108.6
C3—C2—H2	120.5	C15—C14—H14B	108.6
C1—C2—H2	120.5	H14A—C14—H14B	107.6
C4—C3—C2	119.1 (5)	N5—C15—C16	121.5 (5)
C4—C3—H3	120.5	N5—C15—C14	114.5 (4)
C2—C3—H3	120.5	C16—C15—C14	124.0 (4)
C3—C4—C5	120.3 (5)	C17—C16—C15	119.7 (6)
C3—C4—H4	119.8	C17—C16—H16	120.1
C5—C4—H4	119.8	C15—C16—H16	120.1
N1—C5—C4	121.1 (4)	C18—C17—C16	119.0 (6)
N1—C5—C6	117.7 (4)	C18—C17—H17	120.5
C4—C5—C6	121.3 (4)	C16—C17—H17	120.5
N2—C6—C5	113.6 (4)	C17—C18—C19	118.9 (6)
N2—C6—H6A	108.8	C17—C18—H18	120.6
C5—C6—H6A	108.8	C19—C18—H18	120.6
N2—C6—H6B	108.8	N5—C19—C18	122.6 (6)
C5—C6—H6B	108.8	N5—C19—H19	118.7
H6A—C6—H6B	107.7	C18—C19—H19	118.7
O2—C7—N2	124.5 (5)
O1—Zn1—N1—C5	−66.2 (4)	N2—C7—C8—C9	179.6 (4)
Cl2—Zn1—N1—C5	−179.7 (3)	N3—C8—C9—C10	−1.3 (7)
Cl1—Zn1—N1—C5	50.3 (4)	C7—C8—C9—C10	179.0 (4)
O1—Zn1—N1—C1	115.3 (3)	C8—C9—C10—C11	1.2 (7)
Cl2—Zn1—N1—C1	1.7 (3)	C9—C10—C11—C12	−0.9 (7)
Cl1—Zn1—N1—C1	−128.2 (3)	C8—N3—C12—C11	−0.6 (6)
C5—N1—C1—C2	−0.8 (6)	C8—N3—C12—C13	178.9 (4)
Zn1—N1—C1—C2	177.8 (3)	C10—C11—C12—N3	0.6 (7)
N1—C1—C2—C3	1.8 (7)	C10—C11—C12—C13	−178.9 (4)
C1—C2—C3—C4	−1.3 (8)	C14—N4—C13—O3	4.0 (7)
C2—C3—C4—C5	−0.2 (8)	C14—N4—C13—C12	−175.1 (4)
C1—N1—C5—C4	−0.7 (6)	N3—C12—C13—O3	−172.5 (4)
Zn1—N1—C5—C4	−179.2 (3)	C11—C12—C13—O3	7.0 (6)
C1—N1—C5—C6	177.5 (4)	N3—C12—C13—N4	6.6 (6)
Zn1—N1—C5—C6	−1.0 (5)	C11—C12—C13—N4	−173.9 (4)
C3—C4—C5—N1	1.2 (7)	C13—N4—C14—C15	−82.1 (5)
C3—C4—C5—C6	−176.9 (5)	C19—N5—C15—C16	0.5 (7)
C7—N2—C6—C5	−85.4 (5)	C19—N5—C15—C14	−178.5 (5)
N1—C5—C6—N2	129.6 (4)	N4—C14—C15—N5	164.5 (4)
C4—C5—C6—N2	−52.2 (6)	N4—C14—C15—C16	−14.4 (7)
C6—N2—C7—O2	1.8 (7)	N5—C15—C16—C17	−0.7 (8)
C6—N2—C7—C8	−177.9 (4)	C14—C15—C16—C17	178.1 (5)
C12—N3—C8—C9	1.0 (6)	C15—C16—C17—C18	0.2 (8)
C12—N3—C8—C7	−179.3 (4)	C16—C17—C18—C19	0.5 (9)
O2—C7—C8—N3	−179.9 (4)	C15—N5—C19—C18	0.3 (8)
N2—C7—C8—N3	−0.2 (6)	C17—C18—C19—N5	−0.8 (9)
O2—C7—C8—C9	−0.1 (7)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1A···O2	0.82	1.88	2.695 (5)	171
O1—H1B···N5^i	0.85	1.89	2.723 (6)	167
N2—H2A···N3	0.86	2.32	2.707 (5)	108
N2—H2A···Cl1^ii	0.86	2.59	3.356 (4)	149
N4—H4A···N3	0.86	2.35	2.720 (6)	106
N4—H4A···Cl1^ii	0.86	2.62	3.364 (4)	145
C1—H1···O3^iii	0.93	2.36	3.140 (6)	142

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