A new two-dimensional folding sheet-like coordination polymer assembled from cadmium(II) and (S)-2-(benzyl­amino)­succinic acid: synthesis, structure and properties

A new two-dimensional (2D) coordination polymer, namely, poly[[di­aqua­[μ₃-(S)-2-(benzyl­amino)­succinato-κ⁴N,O¹:O^1′:O⁴]cadmium(II)] monohydrate], {[Cd(C₁₁H₁₁NO₄)(H₂O)₂]·H₂O}_n, has been synthesized by the solvothermal reaction of Cd(CH₃COO)₂·2H₂O with the synthesized ligand (S)-2-(benzyl­amino)­succinic acid (H₂L). The title com­pound has been structurally characterized by elemental analysis, IR spectroscopy and single-crystal X-ray diffraction analysis. In the crystal structure, each Cd^II cation binds to three car­box­yl­ate groups from three symmetry-related L²⁻ dianions. The tetra­dentate L²⁻ ligand links three symmetry-related Cd^II cations into a 2D folding sheet, which can be simplified as a uninodal (3,3)-connected hcb net with the point symbol (6³). In the lattice, all the folding sheets are arranged in an inter­digitated fashion and aggregate into zipper-like arrays through inter­layer π–π inter­actions. The large and nonpolar side chain may play an important role in the formation and aggregation of the 2D sheet. The thermal stability and photoluminescence properties of the title com­pound were investigated, and it exhibits a blue emission with a quantum yield of 8%.

Computing details

Data collection: APEX2 (Bruker, 2004); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT (Bruker, 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015); molecular graphics: DIAMOND (Brandenburg, 2008).

Poly[[diaqua[µ₃-(S)-2-(benzylamino)succinato-κ⁴N,O¹:O^1':O⁴]cadmium(II)] monohydrate]

Crystal data

[Cd(C11H11NO4)(H2O)2]·H2O	F(000) = 388
Mr = 387.65	Dx = 1.903 Mg m^−3
Monoclinic, P21	Mo Kα radiation, λ = 0.71073 Å
a = 5.8737 (9) Å	Cell parameters from 2906 reflections
b = 8.3842 (13) Å	θ = 2.9–27.4°
c = 13.788 (2) Å	µ = 1.65 mm^−1
β = 95.025 (2)°	T = 298 K
V = 676.39 (18) Å^3	Stick, colorless
Z = 2	0.19 × 0.08 × 0.06 mm

Data collection

Bruker APEXII CCD area detector diffractometer	2618 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.034
phi and ω scans	θmax = 27.6°, θmin = 1.5°
Absorption correction: multi-scan (SADABS; Bruker, 2004)	h = −7→7
Tmin = 0.765, Tmax = 0.908	k = −10→10
5888 measured reflections	l = −17→17
2952 independent reflections

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.030	H-atom parameters constrained
wR(F^2) = 0.064	w = 1/[σ^2(Fo^2) + (0.028P)^2 + 0.1306P] where P = (Fo^2 + 2Fc^2)/3
S = 0.94	(Δ/σ)max = 0.001
2952 reflections	Δρmax = 0.49 e Å^−3
181 parameters	Δρmin = −0.73 e Å^−3
163 restraints	Absolute structure: Flack x determined using 1034 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons et al., 2013)
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.02 (3)

Special details

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
C1	0.1300 (10)	1.1079 (7)	0.9031 (5)	0.0219 (13)
C2	0.1356 (10)	1.0916 (7)	0.7942 (4)	0.0209 (12)
H2A	0.1945	1.1898	0.7689	0.025*
H2B	−0.0197	1.0782	0.7651	0.025*
C3	0.2806 (10)	0.9522 (7)	0.7624 (4)	0.0186 (11)
H3	0.3115	0.9725	0.6948	0.022*
C4	0.5138 (10)	0.9421 (8)	0.8227 (4)	0.0209 (12)
C5	0.0106 (10)	0.7718 (9)	0.6718 (4)	0.0251 (16)
H5A	−0.0956	0.8602	0.6623	0.030*
H5B	−0.0787	0.6760	0.6792	0.030*
C6	0.1368 (10)	0.7545 (16)	0.5806 (4)	0.0312 (12)
C7	0.3356 (14)	0.6713 (10)	0.5793 (6)	0.0421 (16)
H7	0.3974	0.6228	0.6363	0.051*
C8	0.4490 (16)	0.6567 (11)	0.4955 (6)	0.0521 (19)
H8	0.5843	0.5990	0.4960	0.062*
C9	0.3559 (15)	0.7302 (16)	0.4113 (5)	0.0552 (19)
H9	0.4273	0.7191	0.3541	0.066*
C10	0.1607 (17)	0.8188 (10)	0.4110 (6)	0.0526 (19)
H10	0.1020	0.8695	0.3542	0.063*
C11	0.0498 (14)	0.8331 (9)	0.4956 (5)	0.0400 (16)
H11	−0.0818	0.8947	0.4957	0.048*
Cd1	0.96415 (6)	0.74712 (6)	0.90460 (3)	0.02046 (11)
N1	0.1560 (8)	0.7989 (5)	0.7634 (3)	0.0172 (10)
H1	0.2750	0.7169	0.7638	0.021*
O1	0.1267 (6)	1.2448 (10)	0.9390 (2)	0.0273 (8)
O2	0.1289 (8)	0.9843 (5)	0.9540 (3)	0.0265 (10)
O3	0.5961 (7)	0.8057 (5)	0.8413 (3)	0.0293 (11)
O4	0.6078 (8)	1.0714 (6)	0.8485 (4)	0.0290 (11)
O5	1.3199 (8)	0.6231 (5)	0.9575 (3)	0.0304 (11)
H5C	1.4262	0.6906	0.9524	0.037*
H5D	1.3117	0.5849	1.0136	0.037*
O6	0.9241 (8)	0.5040 (5)	0.8279 (3)	0.0288 (10)
H6A	0.7810	0.4793	0.8216	0.035*
H6B	0.9329	0.4305	0.8705	0.035*
O7	0.4959 (10)	0.4009 (7)	0.8164 (4)	0.0433 (14)
H7A	0.4064	0.4804	0.8180	0.052*
H7B	0.4775	0.3390	0.8639	0.052*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.016 (3)	0.029 (3)	0.021 (3)	0.002 (2)	0.002 (2)	−0.001 (3)
C2	0.020 (3)	0.022 (3)	0.021 (3)	0.000 (2)	0.001 (2)	0.001 (2)
C3	0.019 (3)	0.022 (3)	0.015 (3)	−0.003 (2)	0.000 (2)	0.000 (2)
C4	0.014 (3)	0.031 (3)	0.019 (3)	−0.001 (2)	0.005 (2)	−0.002 (2)
C5	0.023 (3)	0.034 (4)	0.018 (3)	−0.005 (3)	−0.002 (2)	−0.002 (3)
C6	0.036 (3)	0.037 (3)	0.020 (2)	−0.009 (4)	−0.001 (2)	−0.005 (4)
C7	0.047 (4)	0.050 (3)	0.030 (3)	0.003 (3)	0.008 (3)	−0.005 (3)
C8	0.055 (4)	0.060 (4)	0.042 (4)	0.003 (4)	0.011 (4)	−0.009 (3)
C9	0.075 (4)	0.058 (5)	0.035 (3)	−0.001 (5)	0.020 (3)	−0.004 (4)
C10	0.071 (5)	0.055 (4)	0.032 (4)	−0.004 (4)	0.003 (4)	0.006 (3)
C11	0.051 (4)	0.042 (3)	0.027 (3)	0.002 (3)	−0.002 (3)	0.002 (3)
Cd1	0.01802 (18)	0.02181 (17)	0.02179 (19)	−0.0004 (3)	0.00304 (13)	0.0003 (3)
N1	0.016 (2)	0.018 (2)	0.018 (2)	−0.0013 (17)	0.0025 (19)	−0.0013 (17)
O1	0.038 (2)	0.0208 (16)	0.0243 (19)	−0.007 (5)	0.0081 (16)	0.002 (4)
O2	0.036 (3)	0.025 (2)	0.018 (2)	−0.0050 (19)	0.005 (2)	0.0002 (18)
O3	0.018 (2)	0.032 (2)	0.038 (3)	0.0054 (17)	0.002 (2)	0.0025 (19)
O4	0.019 (3)	0.031 (3)	0.037 (3)	−0.004 (2)	−0.002 (2)	−0.004 (2)
O5	0.027 (3)	0.034 (3)	0.031 (3)	0.003 (2)	0.002 (2)	0.014 (2)
O6	0.033 (3)	0.025 (2)	0.028 (3)	−0.005 (2)	0.002 (2)	0.0018 (19)
O7	0.034 (3)	0.040 (3)	0.057 (4)	−0.009 (3)	0.013 (3)	0.005 (3)

Geometric parameters (Å, º)

C1—O1	1.250 (9)	C9—H9	0.9300
C1—O2	1.252 (7)	C10—C11	1.390 (11)
C1—C2	1.511 (8)	C10—H10	0.9300
C2—C3	1.533 (8)	C11—H11	0.9300
C2—H2A	0.9700	Cd1—O1^i	2.267 (3)
C2—H2B	0.9700	Cd1—O2^ii	2.289 (4)
C3—N1	1.480 (7)	Cd1—O6	2.298 (4)
C3—C4	1.541 (8)	Cd1—O3	2.312 (4)
C3—H3	0.9800	Cd1—N1^ii	2.374 (5)
C4—O4	1.254 (8)	Cd1—O5	2.390 (4)
C4—O3	1.259 (7)	N1—Cd1^iii	2.374 (5)
C5—N1	1.478 (7)	N1—H1	0.9800
C5—C6	1.521 (8)	O1—Cd1^iv	2.267 (3)
C5—H5A	0.9700	O2—Cd1^iii	2.289 (4)
C5—H5B	0.9700	O5—H5C	0.8504
C6—C7	1.362 (11)	O5—H5D	0.8421
C6—C11	1.402 (10)	O6—H6A	0.8625
C7—C8	1.389 (11)	O6—H6B	0.8500
C7—H7	0.9300	O7—O7	0.000 (18)
C8—C9	1.384 (12)	O7—H7A	0.8500
C8—H8	0.9300	O7—H7B	0.8500
C9—C10	1.365 (13)
O1—C1—O2	122.5 (6)	C11—C10—H10	120.0
O1—C1—C2	118.6 (5)	C10—C11—C6	119.9 (8)
O2—C1—C2	118.9 (5)	C10—C11—H11	120.1
C1—C2—C3	114.5 (5)	C6—C11—H11	120.1
C1—C2—H2A	108.6	O1^i—Cd1—O2^ii	81.6 (2)
C3—C2—H2A	108.6	O1^i—Cd1—O6	114.0 (2)
C1—C2—H2B	108.6	O2^ii—Cd1—O6	158.56 (15)
C3—C2—H2B	108.6	O1^i—Cd1—O3	94.07 (15)
H2A—C2—H2B	107.6	O2^ii—Cd1—O3	106.53 (16)
N1—C3—C2	111.8 (5)	O6—Cd1—O3	87.70 (16)
N1—C3—C4	111.4 (5)	O1^i—Cd1—N1^ii	161.88 (18)
C2—C3—C4	112.2 (5)	O2^ii—Cd1—N1^ii	82.33 (15)
N1—C3—H3	107.0	O6—Cd1—N1^ii	79.72 (16)
C2—C3—H3	107.0	O3—Cd1—N1^ii	98.42 (16)
C4—C3—H3	107.0	O1^i—Cd1—O5	88.75 (16)
O4—C4—O3	125.2 (6)	O2^ii—Cd1—O5	87.24 (16)
O4—C4—C3	117.0 (6)	O6—Cd1—O5	78.83 (16)
O3—C4—C3	117.8 (5)	O3—Cd1—O5	166.20 (16)
N1—C5—C6	115.7 (5)	N1^ii—Cd1—O5	82.23 (16)
N1—C5—H5A	108.4	C5—N1—C3	112.0 (5)
C6—C5—H5A	108.4	C5—N1—Cd1^iii	113.1 (3)
N1—C5—H5B	108.4	C3—N1—Cd1^iii	115.9 (3)
C6—C5—H5B	108.4	C5—N1—H1	104.8
H5A—C5—H5B	107.4	C3—N1—H1	104.8
C7—C6—C11	118.7 (6)	Cd1^iii—N1—H1	104.8
C7—C6—C5	122.7 (7)	C1—O1—Cd1^iv	113.4 (5)
C11—C6—C5	118.6 (7)	C1—O2—Cd1^iii	125.2 (4)
C6—C7—C8	122.0 (7)	C4—O3—Cd1	126.8 (4)
C6—C7—H7	119.0	Cd1—O5—H5C	108.3
C8—C7—H7	119.0	Cd1—O5—H5D	109.1
C9—C8—C7	118.4 (8)	H5C—O5—H5D	115.5
C9—C8—H8	120.8	Cd1—O6—H6A	108.6
C7—C8—H8	120.8	Cd1—O6—H6B	109.1
C10—C9—C8	121.0 (8)	H6A—O6—H6B	84.0
C10—C9—H9	119.5	O7—O7—H7A	0.0
C8—C9—H9	119.5	O7—O7—H7B	0.0
C9—C10—C11	119.9 (8)	H7A—O7—H7B	109.7
C9—C10—H10	120.0
O1—C1—C2—C3	143.6 (5)	C9—C10—C11—C6	−1.0 (14)
O2—C1—C2—C3	−36.5 (8)	C7—C6—C11—C10	3.0 (14)
C1—C2—C3—N1	80.6 (6)	C5—C6—C11—C10	−179.6 (8)
C1—C2—C3—C4	−45.4 (7)	C6—C5—N1—C3	64.1 (9)
N1—C3—C4—O4	−161.9 (5)	C6—C5—N1—Cd1^iii	−162.6 (6)
C2—C3—C4—O4	−35.7 (7)	C2—C3—N1—C5	85.2 (6)
N1—C3—C4—O3	18.9 (7)	C4—C3—N1—C5	−148.4 (5)
C2—C3—C4—O3	145.0 (6)	C2—C3—N1—Cd1^iii	−46.6 (6)
N1—C5—C6—C7	40.6 (13)	C4—C3—N1—Cd1^iii	79.8 (5)
N1—C5—C6—C11	−136.7 (8)	O2—C1—O1—Cd1^iv	−13.5 (7)
C11—C6—C7—C8	−2.7 (14)	C2—C1—O1—Cd1^iv	166.5 (4)
C5—C6—C7—C8	−179.9 (8)	O1—C1—O2—Cd1^iii	148.0 (4)
C6—C7—C8—C9	0.3 (14)	C2—C1—O2—Cd1^iii	−32.0 (8)
C7—C8—C9—C10	1.8 (16)	O4—C4—O3—Cd1	−10.9 (9)
C8—C9—C10—C11	−1.5 (16)	C3—C4—O3—Cd1	168.2 (4)

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

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C5—H5B···O6^iii	0.97	2.51	3.182 (8)	127
C2—H2B···O4^iii	0.97	2.56	3.256 (8)	129
C2—H2A···O7^v	0.97	2.55	3.345 (8)	139
O7—H7B···O4^vi	0.85	2.39	2.865 (7)	116
O7—H7B···O1^vi	0.85	2.51	3.149 (7)	132
O7—H7A···O5^iii	0.85	2.36	2.945 (7)	127
O6—H6B···O2^i	0.85	2.52	3.055 (6)	122
O6—H6B···O1^vii	0.85	2.10	2.858 (8)	148
O6—H6A···O7	0.86	1.79	2.651 (7)	172
O5—H5D···O4^viii	0.84	1.92	2.706 (7)	154
O5—H5C···O3^ii	0.85	2.13	2.829 (6)	139
N1—H1···O3	0.98	2.21	2.712 (6)	110

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