catena-Poly[[[(acetato-κ2O,O′)aqua­cadmium(II)]-μ-l-threoninato-κ3N,O:O′] monohydrate]

Abila Jeba Queen, M.; Bright, K.C.; Mary Delphine, S.

doi:10.1107/S2414314618017704

metal-organic compounds

IUCrDATA

ISSN: 2414-3146

Volume 3| Part 12| December 2018| x181770

https://doi.org/10.1107/S2414314618017704

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catena-Poly[[[(acetato-κ²O,O′)aquacadmium(II)]-μ-L-threoninato-κ³N,O:O′] monohydrate]

M. Abila Jeba Queen,^a ^*‡ K. C. Bright ^b and S. Mary Delphine ^a

^aDepartment of Physics, Holy Cross College (Autonomous), Nagercoil-629004, Tamil Nadu, India, and ^bDepartment of Physics, St. John's College, Anchal-691306, Kerala, India
^*Correspondence e-mail: jeba.abi@gmail.com

Edited by S. Bernès, Benemérita Universidad Autónoma de Puebla, México (Received 6 September 2018; accepted 14 December 2018; online 21 December 2018)

The title compound, {[Cd(C₂H₃O₂)(C₄H₈NO₃)(H₂O)]·H₂O}_n, was synthesized from the reaction between L-threonine and cadmium acetate dihydrate. The complex consists of the Cd^II metal ion bonded to bidentate threonine and acetate anions, and one water molecule. The carboxylate group of L-threonine bridges two metal cations related by the crystallographic screw axis parallel to [010], to form a one-dimensional polymeric structure in the crystal. The asymmetric unit is completed by one lattice water molecule, which is involved in hydrogen bonds.

Keywords: crystal structure; L-threonine; cadmium acetate; hydrogen bonding.

CCDC reference: 1885062

Structure description

L-threonine [IUPAC name: (2S,3R)-2-amino-3-hydroxybutanoic acid] has wide applications in industry, for example as an additive, or as a precursor for the biosynthesis of other chemicals (Dong et al., 2012 ). On the other hand, cadmium acetate is used for glazing ceramics and pottery, in electroplating baths, in dyeing and printing textiles, and as an analytic reagent (Patnaik, 2003 ).

In the asymmetric unit of the title compound (Fig. 1) the Cd1—O1 bond length, 2.306 (4) Å, is in agreement with the distances reported in other cadmium acetate compounds (Vickers et al., 2011 ). In the threonine ligand, C2—C3 [1.537 (7) Å] and C2—N1 [1.472 (6) Å] bond lengths are consistent with those reported for free L-threonine [1.532 (2) and 1.491 (2) Å, respectively; Janczak et al., 1997 ; X-ray data at 12 K].

Figure 1
The asymmetric unit of the title complex, with displacement ellipsoids for non-H atoms at the 50% probability level.

In the complex molecule, the Cd^II ion is found to be in a six-coordination environment: the metal cation is coordinated by one carboxylate O atom and one amine N atom of the bidentate threonine ligand, two O atoms from the bidentate acetate ligand and one water molecule. Finally, one carboxylate O atom of the threonine ligand forms a bridge with a symmetry-related metal ion, completing the coordination sphere of the metal, and giving a polymeric crystal structure along the [010] direction (Fig. 2). The O—Cd—O bond angles range from 53.95 (14) to 162.36 (14)°.

Figure 2
The polymeric structure of the title compound.

In the crystal structure, hydrogen bonds are formed, with all N—H and O—H groups from the L-threonine and water molecules serving as donor groups (Table 1), affording a layered supramolecular structure extending parallel to the [010] plane (Fig. 3).

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O5—H5⋯O7ⁱ	0.82	1.90	2.701 (6)	164
N1—H1A⋯O4ⁱⁱ	0.89 (3)	2.21 (3)	3.083 (5)	170 (5)
N1—H1B⋯O3ⁱⁱⁱ	0.89 (3)	2.28 (4)	2.983 (5)	136 (4)
O6—H6D⋯O5ⁱ	0.89 (3)	1.86 (3)	2.753 (5)	175 (6)
O6—H6E⋯O2^iv	0.88 (3)	1.80 (3)	2.676 (6)	174 (7)
O7—H7A⋯O1	0.89 (3)	1.84 (4)	2.707 (6)	163 (9)
O7—H7B⋯O6^v	0.88 (3)	2.46 (5)	3.290 (7)	157 (9)
Symmetry codes: (i) $[-x, y+{\script{1\over 2}}, -z]$ ; (ii) $[-x+1, y-{\script{1\over 2}}, -z]$ ; (iii) $[-x, y-{\script{1\over 2}}, -z]$ ; (iv) x-1, y, z; (v) $[-x, y-{\script{1\over 2}}, -z+1]$ .

Figure 3
Packing diagram of the title complex viewed down the a axis, showing one polymeric chain forming hydrogen bonds (dashed blue lines) with lattice water molecules.

Synthesis and crystallization

Crystals of the title compound were prepared by adding L-threonine to an aqueous solution of cadmium acetate dihydrate in a stoichiometric ratio. Good quality single crystals were grown by repeated crystallization of an aqueous solution of the complex, at room temperature, over several weeks.

Refinement

Crystal data, data collection and structure refinement details are summarized in Table 2.

Table 2
Experimental details

Crystal data
Chemical formula	[Cd(C₂H₃O₂)(C₄H₈NO₃)(H₂O)]·H₂O
M_r	325.59
Crystal system, space group	Monoclinic, P2₁
Temperature (K)	293
a, b, c (Å)	5.8199 (12), 8.8017 (16), 10.710 (2)
β (°)	91.916 (6)
V (Å³)	548.30 (18)
Z	2
Radiation type	Mo Kα
μ (mm⁻¹)	2.01
Crystal size (mm)	0.20 × 0.15 × 0.10

Data collection
Diffractometer	Bruker Kappa APEXII CCD
Absorption correction	Multi-scan (SADABS; Bruker, 2004 )
T_min, T_max	0.593, 0.746
No. of measured, independent and observed [I > 2σ(I)] reflections	4756, 2373, 2215
R_int	0.027
(sin θ/λ)_max (Å⁻¹)	0.639

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.021, 0.048, 1.06
No. of reflections	2373
No. of parameters	162
No. of restraints	7
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.29, −0.44
Absolute structure	Flack x determined using 960 quotients [(I⁺)−(I⁻)]/[(I⁺)+(I⁻)] (Parsons et al., 2013 )
Absolute structure parameter	−0.02 (2)
Computer programs: APEX2, SAINT and XPREP (Bruker, 2004), SHELXT2014 (Sheldrick, 2015a ), SHELXL2014 (Sheldrick, 2015b ), ORTEP-3 for Windows (Farrugia, 2012 ) and Mercury (Macrae et al., 2008 ).

Structural data

CCDC reference: 1885062

Crystal structure: contains datablock I. DOI: https://doi.org/10.1107/S2414314618017704/bh4041sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2414314618017704/bh4041Isup2.hkl

checkCIF report

Computing details top

Data collection: APEX2 (Bruker, 2004); cell refinement: APEX2 and SAINT (Bruker, 2004); data reduction: SAINT and XPREP (Bruker, 2004); program(s) used to solve structure: SHELXT2014 (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015b); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012) and Mercury (Macrae et al., 2008); software used to prepare material for publication: SHELXL2014 (Sheldrick, 2015b).

catena-Poly[[[(acetato-κ²O,O')aquacadmium(II)]-µ-L-threoninato-κ³N,O:O'] monohydrate] top

Crystal data top

[Cd(C₂H₃O₂)(C₄H₈NO₃)(H₂O)]·H₂O	F(000) = 324
M_r = 325.59	D_x = 1.972 Mg m⁻³
Monoclinic, P2₁	Mo Kα radiation, λ = 0.71073 Å
a = 5.8199 (12) Å	Cell parameters from 2960 reflections
b = 8.8017 (16) Å	θ = 3.0–30.4°
c = 10.710 (2) Å	µ = 2.01 mm⁻¹
β = 91.916 (6)°	T = 293 K
V = 548.30 (18) Å³	Block, colourless
Z = 2	0.20 × 0.15 × 0.10 mm

Data collection top

Bruker Kappa APEXII CCD diffractometer	2373 independent reflections
Radiation source: fine-focus sealed tube	2215 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.027
ω and φ scan	θ_max = 27.0°, θ_min = 3.0°
Absorption correction: multi-scan (SADABS; Bruker, 2004)	h = −4→7
T_min = 0.593, T_max = 0.746	k = −10→11
4756 measured reflections	l = −13→13

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: mixed
R[F² > 2σ(F²)] = 0.021	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.048	w = 1/[σ²(F_o²) + (0.0151P)²] where P = (F_o² + 2F_c²)/3
S = 1.06	(Δ/σ)_max < 0.001
2373 reflections	Δρ_max = 0.29 e Å⁻³
162 parameters	Δρ_min = −0.43 e Å⁻³
7 restraints	Absolute structure: Flack x determined using 960 quotients [(I⁺)-(I^-)]/[(I⁺)+(I^-)] (Parsons et al., 2013)
Primary atom site location: dual	Absolute structure parameter: −0.02 (2)

Special details top

Refinement. The atomic positions of H atoms bonded to C atoms and hydroxyl atom O5 were calculated, and these H atoms were refined as riding to their parent atoms, with an isotropic displacement parameter calculated as U_iso = 1.2–1.5U_eq(carrier atom). Water and amine H atoms were located in difference maps and refined freely. For these H atoms, N—H and O—H bond lengths were restrained to 0.90 (2) Å.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
C1	0.1873 (8)	0.6187 (5)	−0.0589 (4)	0.0198 (10)
C2	0.3744 (8)	0.4946 (5)	−0.0609 (4)	0.0195 (10)
H2	0.5147	0.5378	−0.0222	0.023*
C3	0.4290 (8)	0.4515 (5)	−0.1958 (5)	0.0259 (13)
H3	0.4545	0.5438	−0.2446	0.031*
C4	0.6394 (9)	0.3493 (7)	−0.2005 (5)	0.0341 (13)
H4A	0.6058	0.2529	−0.1633	0.051*
H4B	0.7657	0.3962	−0.1552	0.051*
H4C	0.6794	0.3344	−0.2859	0.051*
C5	0.3471 (10)	0.3480 (7)	0.3548 (5)	0.0285 (12)
C6	0.5144 (12)	0.2946 (8)	0.4545 (6)	0.0476 (16)
H6A	0.4398	0.2238	0.5080	0.071*
H6B	0.5688	0.3799	0.5028	0.071*
H6C	0.6420	0.2457	0.4166	0.071*
N1	0.3104 (7)	0.3621 (4)	0.0142 (4)	0.0198 (9)
O1	0.1723 (8)	0.2697 (5)	0.3282 (4)	0.0481 (12)
O2	0.3858 (7)	0.4672 (5)	0.2946 (4)	0.0353 (10)
O3	0.0128 (6)	0.5995 (4)	0.0047 (4)	0.0272 (8)
O4	0.2300 (6)	0.7358 (4)	−0.1214 (3)	0.0265 (8)
O5	0.2331 (6)	0.3716 (3)	−0.2470 (3)	0.0285 (9)
H5	0.1896	0.4121	−0.3125	0.043*
O6	−0.1803 (7)	0.5625 (5)	0.2746 (4)	0.0394 (10)
O7	−0.0219 (9)	0.0255 (6)	0.4365 (4)	0.0514 (12)
Cd1	0.04345 (4)	0.41168 (6)	0.15898 (3)	0.02231 (10)
H1A	0.432 (6)	0.316 (6)	0.048 (4)	0.022 (14)*
H1B	0.253 (8)	0.286 (4)	−0.031 (4)	0.007 (12)*
H6D	−0.189 (11)	0.663 (3)	0.264 (6)	0.05 (2)*
H6E	−0.326 (6)	0.537 (8)	0.278 (6)	0.06 (2)*
H7A	0.052 (16)	0.110 (7)	0.416 (8)	0.10 (3)*
H7B	−0.009 (18)	0.045 (10)	0.517 (3)	0.09 (3)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.023 (2)	0.015 (2)	0.021 (2)	0.0010 (19)	−0.0055 (19)	−0.0012 (19)
C2	0.018 (2)	0.017 (2)	0.023 (2)	−0.0004 (19)	−0.0003 (19)	0.002 (2)
C3	0.025 (2)	0.029 (4)	0.024 (2)	−0.0021 (18)	−0.0003 (18)	0.0040 (19)
C4	0.028 (3)	0.048 (3)	0.027 (3)	0.009 (2)	0.003 (2)	−0.006 (2)
C5	0.034 (3)	0.034 (3)	0.018 (3)	0.006 (2)	0.001 (2)	−0.001 (3)
C6	0.049 (4)	0.053 (4)	0.039 (3)	0.001 (3)	−0.015 (3)	0.004 (3)
N1	0.023 (2)	0.012 (2)	0.024 (2)	0.0013 (15)	−0.0024 (17)	0.0017 (16)
O1	0.044 (2)	0.053 (3)	0.046 (2)	−0.020 (2)	−0.017 (2)	0.025 (2)
O2	0.036 (2)	0.033 (2)	0.036 (2)	−0.0059 (17)	−0.006 (2)	0.0043 (19)
O3	0.0255 (17)	0.0204 (17)	0.0359 (19)	0.0047 (16)	0.0052 (15)	0.0076 (16)
O4	0.0274 (18)	0.0158 (17)	0.036 (2)	0.0014 (14)	−0.0011 (16)	0.0077 (15)
O5	0.0328 (17)	0.025 (3)	0.0270 (17)	0.0011 (14)	−0.0069 (14)	−0.0011 (13)
O6	0.034 (2)	0.027 (2)	0.058 (3)	−0.0007 (18)	0.017 (2)	−0.006 (2)
O7	0.069 (3)	0.043 (3)	0.041 (3)	−0.021 (2)	−0.014 (2)	0.006 (2)
Cd1	0.02215 (14)	0.02029 (16)	0.02456 (16)	−0.0006 (2)	0.00159 (10)	0.0020 (2)

Geometric parameters (Å, º) top

C1—O3	1.252 (6)	C6—H6B	0.9600
C1—O4	1.259 (6)	C6—H6C	0.9600
C1—C2	1.543 (6)	N1—Cd1	2.274 (4)
C2—N1	1.472 (6)	N1—H1A	0.89 (3)
C2—C3	1.537 (7)	N1—H1B	0.89 (3)
C2—H2	0.9800	O1—Cd1	2.306 (4)
C3—O5	1.432 (6)	O2—Cd1	2.475 (4)
C3—C4	1.521 (7)	O3—Cd1	2.340 (3)
C3—H3	0.9800	O4—Cd1ⁱ	2.247 (3)
C4—H4A	0.9600	O5—H5	0.8200
C4—H4B	0.9600	O6—Cd1	2.258 (4)
C4—H4C	0.9600	O6—H6D	0.89 (3)
C5—O1	1.254 (7)	O6—H6E	0.88 (3)
C5—O2	1.255 (6)	O7—H7A	0.89 (3)
C5—C6	1.497 (8)	O7—H7B	0.88 (3)
C5—Cd1	2.755 (6)	Cd1—O4ⁱⁱ	2.247 (3)
C6—H6A	0.9600

O3—C1—O4	125.3 (4)	Cd1—N1—H1A	111 (3)
O3—C1—C2	119.9 (4)	C2—N1—H1B	113 (3)
O4—C1—C2	114.8 (4)	Cd1—N1—H1B	105 (3)
N1—C2—C3	112.4 (4)	H1A—N1—H1B	99 (4)
N1—C2—C1	111.2 (4)	C5—O1—Cd1	96.9 (3)
C3—C2—C1	110.9 (4)	C5—O2—Cd1	88.9 (4)
N1—C2—H2	107.4	C1—O3—Cd1	115.8 (3)
C3—C2—H2	107.4	C1—O4—Cd1ⁱ	120.6 (3)
C1—C2—H2	107.4	C3—O5—H5	109.5
O5—C3—C4	109.2 (4)	Cd1—O6—H6D	123 (4)
O5—C3—C2	107.1 (4)	Cd1—O6—H6E	117 (5)
C4—C3—C2	111.6 (4)	H6D—O6—H6E	102 (6)
O5—C3—H3	109.6	H7A—O7—H7B	93 (8)
C4—C3—H3	109.6	O4ⁱⁱ—Cd1—O6	94.90 (13)
C2—C3—H3	109.6	O4ⁱⁱ—Cd1—N1	103.98 (13)
C3—C4—H4A	109.5	O6—Cd1—N1	155.03 (14)
C3—C4—H4B	109.5	O4ⁱⁱ—Cd1—O1	88.69 (14)
H4A—C4—H4B	109.5	O6—Cd1—O1	93.77 (18)
C3—C4—H4C	109.5	N1—Cd1—O1	102.74 (15)
H4A—C4—H4C	109.5	O4ⁱⁱ—Cd1—O3	108.86 (13)
H4B—C4—H4C	109.5	O6—Cd1—O3	86.58 (15)
O1—C5—O2	120.1 (5)	N1—Cd1—O3	72.03 (13)
O1—C5—C6	119.5 (5)	O1—Cd1—O3	162.36 (14)
O2—C5—C6	120.4 (6)	O4ⁱⁱ—Cd1—O2	142.44 (13)
O1—C5—Cd1	56.2 (3)	O6—Cd1—O2	91.69 (16)
O2—C5—Cd1	64.0 (3)	N1—Cd1—O2	83.30 (14)
C6—C5—Cd1	173.0 (4)	O1—Cd1—O2	53.95 (14)
C5—C6—H6A	109.5	O3—Cd1—O2	108.42 (13)
C5—C6—H6B	109.5	O4ⁱⁱ—Cd1—C5	115.40 (16)
H6A—C6—H6B	109.5	O6—Cd1—C5	93.96 (18)
C5—C6—H6C	109.5	N1—Cd1—C5	92.56 (15)
H6A—C6—H6C	109.5	O1—Cd1—C5	26.87 (15)
H6B—C6—H6C	109.5	O3—Cd1—C5	135.49 (16)
C2—N1—Cd1	114.3 (3)	O2—Cd1—C5	27.10 (14)
C2—N1—H1A	112 (3)

O3—C1—C2—N1	1.9 (6)	C1—C2—N1—Cd1	−21.0 (5)
O4—C1—C2—N1	−179.9 (4)	O2—C5—O1—Cd1	3.6 (5)
O3—C1—C2—C3	127.8 (5)	C6—C5—O1—Cd1	−173.5 (5)
O4—C1—C2—C3	−54.1 (5)	O1—C5—O2—Cd1	−3.3 (5)
N1—C2—C3—O5	55.2 (5)	C6—C5—O2—Cd1	173.8 (5)
C1—C2—C3—O5	−70.0 (5)	O4—C1—O3—Cd1	−160.1 (4)
N1—C2—C3—C4	−64.3 (5)	C2—C1—O3—Cd1	17.8 (5)
C1—C2—C3—C4	170.5 (4)	O3—C1—O4—Cd1ⁱ	−12.8 (7)
C3—C2—N1—Cd1	−146.0 (3)	C2—C1—O4—Cd1ⁱ	169.2 (3)

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O5—H5···O7ⁱ	0.82	1.90	2.701 (6)	164
N1—H1A···O4ⁱⁱⁱ	0.89 (3)	2.21 (3)	3.083 (5)	170 (5)
N1—H1B···O3ⁱⁱ	0.89 (3)	2.28 (4)	2.983 (5)	136 (4)
O6—H6D···O5ⁱ	0.89 (3)	1.86 (3)	2.753 (5)	175 (6)
O6—H6E···O2^iv	0.88 (3)	1.80 (3)	2.676 (6)	174 (7)
O7—H7A···O1	0.89 (3)	1.84 (4)	2.707 (6)	163 (9)
O7—H7B···O6^v	0.88 (3)	2.46 (5)	3.290 (7)	157 (9)

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

Footnotes

‡Research scholar at Manonmaniam Sundaranar University, Abishekapatti, Tirunelveli, Tamil Nadu, India.

Acknowledgements

We are grateful to the SAIF, IIT Madras, for use of the X-ray data collection facility.

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