Bis­[N-(4-hydroxy­benzyl)-D,L-alaninato]copper(II) tetrahydrate

The title complex has a mononuclear structure, [Cu(C₁₀H₁₂NO₃)₂]·4H₂O, which is a centrosymmetric unit with both D and L-sala ligands [sala = N-(4-hydroxy­benzyl)­alanine] coord­inated to the Cu^II center. Hydro­gen bonding results in a three-dimensional supramolecular structure.

Key indicators

• Single-crystal X-ray study
• T = 173 K
• Mean [sigma](C-C) = 0.004 Å
• R factor = 0.042
• wR factor = 0.094
• Data-to-parameter ratio = 15.1

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low .......       0.96
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ ....          ?
PLAT417_ALERT_2_C Short Inter D-H..H-D       H3     ..  H7      ..       2.11 Ang.
PLAT764_ALERT_4_C Overcomplete CIF Bond List Detected (Rep/Expd) .       1.20 Ratio

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   4 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
   1 ALERT type 2 Indicator that the structure model may be wrong or deficient
   1 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: CrystalClear (Rigaku, 2000); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXL97; software used to prepare material for publication: SHELXL97.

Bis[N-(4-hydroxybenzyl)-D,L-alanine]copper(II) tetrahydrate

Crystal data

[Cu(C10H12NO3)2]·4H2O	F(000) = 550
Mr = 524.02	Dx = 1.479 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2484 reflections
a = 11.5535 (19) Å	θ = 3.1–27.5°
b = 9.3028 (11) Å	µ = 0.99 mm^−1
c = 11.6612 (19) Å	T = 173 K
β = 110.097 (9)°	Prism, blue
V = 1177.0 (3) Å^3	0.15 × 0.10 × 0.05 mm
Z = 2

Data collection

Mercury CCD diffractometer	2603 independent reflections
Radiation source: fine-focus sealed tube	2124 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.041
Detector resolution: 14.6306 pixels mm^-1	θmax = 27.5°, θmin = 3.1°
ω scans	h = −12→14
Absorption correction: multi_scan (CrystalClear; Rigaku, 2000)	k = −12→11
Tmin = 0.866, Tmax = 0.952	l = −14→14
8837 measured reflections

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)] = 0.042	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.094	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	w = 1/[σ^2(Fo^2) + (0.0412P)^2 + 0.689P] where P = (Fo^2 + 2Fc^2)/3
2603 reflections	(Δ/σ)max < 0.001
172 parameters	Δρmax = 0.34 e Å^−3
0 restraints	Δρmin = −0.26 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
Cu1	0.0000	0.5000	0.0000	0.02105 (13)
O1	0.09781 (15)	0.66941 (18)	0.33004 (15)	0.0230 (4)
O5	−0.09919 (17)	0.7390 (2)	−0.11367 (18)	0.0260 (4)
O2	−0.00863 (14)	0.56088 (19)	0.15601 (15)	0.0234 (4)
O3	0.71915 (17)	0.8233 (2)	0.18634 (18)	0.0283 (4)
N1	0.16204 (16)	0.6045 (2)	0.05049 (17)	0.0201 (4)
H1	0.1524	0.6794	−0.0048	0.024*
C10	0.1918 (3)	0.8343 (3)	0.1659 (3)	0.0384 (7)
H10A	0.2611	0.8608	0.1400	0.058*
H10B	0.2044	0.8751	0.2468	0.058*
H10C	0.1151	0.8720	0.1072	0.058*
C9	0.0831 (2)	0.6314 (2)	0.2227 (2)	0.0188 (5)
C8	0.1839 (2)	0.6723 (3)	0.1718 (2)	0.0219 (5)
H8	0.2643	0.6360	0.2295	0.026*
C6	0.5936 (2)	0.6370 (3)	0.2265 (2)	0.0236 (5)
H6	0.6563	0.6130	0.3013	0.028*
C3	0.4100 (2)	0.7050 (3)	0.0094 (2)	0.0305 (6)
H3A	0.3472	0.7292	−0.0654	0.037*
C5	0.4822 (2)	0.5631 (3)	0.1893 (2)	0.0251 (5)
H5	0.4698	0.4884	0.2394	0.030*
C1	0.6123 (2)	0.7453 (3)	0.1539 (2)	0.0210 (5)
C4	0.3890 (2)	0.5959 (3)	0.0808 (2)	0.0224 (5)
C2	0.5205 (2)	0.7797 (3)	0.0446 (2)	0.0303 (6)
H2	0.5333	0.8539	−0.0057	0.036*
C7	0.2672 (2)	0.5156 (3)	0.0432 (2)	0.0245 (5)
H7A	0.2473	0.4809	−0.0416	0.029*
H7B	0.2765	0.4304	0.0965	0.029*
O4	0.1661 (3)	0.4128 (3)	0.4687 (2)	0.0523 (7)
H7	−0.051 (3)	0.772 (3)	−0.137 (3)	0.034 (9)*
H9	0.141 (4)	0.497 (5)	0.434 (4)	0.070 (13)*
H10	−0.111 (3)	0.798 (4)	−0.067 (3)	0.046 (11)*
H4	0.198 (3)	0.381 (4)	0.429 (3)	0.051 (12)*
H3	0.772 (3)	0.791 (4)	0.248 (3)	0.045 (10)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cu1	0.01315 (19)	0.0324 (3)	0.0181 (2)	−0.00720 (16)	0.00599 (15)	−0.00797 (18)
O1	0.0216 (8)	0.0287 (10)	0.0187 (9)	0.0001 (7)	0.0071 (7)	−0.0052 (7)
O5	0.0199 (9)	0.0321 (11)	0.0278 (10)	−0.0014 (8)	0.0105 (8)	0.0017 (9)
O2	0.0175 (8)	0.0317 (9)	0.0227 (9)	−0.0079 (7)	0.0091 (7)	−0.0072 (7)
O3	0.0191 (9)	0.0354 (11)	0.0281 (10)	−0.0099 (7)	0.0049 (8)	0.0018 (8)
N1	0.0154 (9)	0.0265 (11)	0.0184 (10)	−0.0033 (7)	0.0059 (8)	−0.0029 (8)
C10	0.0573 (19)	0.0291 (16)	0.0335 (16)	−0.0163 (13)	0.0216 (14)	−0.0080 (12)
C9	0.0183 (11)	0.0171 (11)	0.0206 (12)	0.0027 (8)	0.0063 (9)	−0.0004 (9)
C8	0.0187 (11)	0.0274 (13)	0.0202 (12)	−0.0045 (9)	0.0074 (10)	−0.0056 (10)
C6	0.0166 (11)	0.0248 (13)	0.0261 (13)	0.0015 (9)	0.0033 (10)	0.0030 (10)
C3	0.0187 (12)	0.0458 (17)	0.0224 (13)	−0.0017 (11)	0.0010 (10)	0.0053 (12)
C5	0.0205 (12)	0.0223 (12)	0.0325 (14)	−0.0009 (9)	0.0092 (10)	0.0045 (11)
C1	0.0147 (10)	0.0234 (12)	0.0256 (13)	−0.0024 (9)	0.0078 (9)	−0.0036 (10)
C4	0.0151 (11)	0.0271 (13)	0.0261 (13)	−0.0011 (9)	0.0085 (10)	−0.0036 (10)
C2	0.0243 (13)	0.0396 (16)	0.0261 (13)	−0.0055 (11)	0.0074 (11)	0.0076 (12)
C7	0.0161 (11)	0.0285 (14)	0.0291 (13)	−0.0037 (9)	0.0080 (10)	−0.0038 (11)
O4	0.0876 (19)	0.0411 (15)	0.0471 (14)	0.0245 (13)	0.0472 (14)	0.0148 (11)

Geometric parameters (Å, º)

Cu1—O2	1.9404 (17)	C9—O1	1.254 (3)
Cu1—O2^i	1.9404 (17)	C9—C8	1.526 (3)
Cu1—N1	2.0096 (18)	C8—H8	1.0000
Cu1—N1^i	2.0096 (18)	C6—C1	1.380 (3)
O1—C9	1.254 (3)	C6—C5	1.390 (3)
O5—O4^ii	2.639 (3)	C6—H6	0.9500
O5—O1^iii	2.714 (3)	C3—C4	1.387 (4)
O5—H7	0.76 (3)	C3—C2	1.386 (3)
O5—H10	0.82 (4)	C3—H3A	0.9500
O2—C9	1.262 (3)	C5—C4	1.384 (3)
O3—C1	1.369 (3)	C5—H5	0.9500
O3—O5^iv	2.611 (3)	C1—C2	1.387 (3)
O3—H3	0.83 (4)	C4—C7	1.519 (3)
N1—C8	1.489 (3)	C2—H2	0.9500
N1—C7	1.495 (3)	C7—H7A	0.9900
N1—H1	0.9300	C7—H7B	0.9900
C10—C8	1.513 (4)	O4—O3^v	2.714 (3)
C10—H10A	0.9800	O4—O1	2.839 (3)
C10—H10B	0.9800	O4—H9	0.88 (4)
C10—H10C	0.9800	O4—H4	0.74 (4)
O2—Cu1—O2^i	180.00 (3)	C10—C8—C9	109.4 (2)
O2—Cu1—N1	85.81 (7)	N1—C8—H8	108.1
O2^i—Cu1—N1	94.19 (7)	C10—C8—H8	108.1
O2—Cu1—N1^i	94.19 (7)	C9—C8—H8	108.1
O2^i—Cu1—N1^i	85.81 (7)	C1—C6—C5	119.5 (2)
N1—Cu1—N1^i	180.0	C1—C6—H6	120.2
O4^ii—O5—O1^iii	114.65 (10)	C5—C6—H6	120.2
O4^ii—O5—H7	113 (2)	C4—C3—C2	121.5 (2)
O1^iii—O5—H10	107 (2)	C4—C3—H3A	119.3
H7—O5—H10	106 (3)	C2—C3—H3A	119.3
C9—O2—Cu1	115.28 (15)	C4—C5—C6	121.5 (2)
C1—O3—O5^iv	120.06 (16)	C4—C5—H5	119.3
C1—O3—H3	112 (2)	C6—C5—H5	119.3
C8—N1—C7	114.35 (18)	O3—C1—C6	122.3 (2)
C8—N1—Cu1	108.66 (13)	O3—C1—C2	117.6 (2)
C7—N1—Cu1	114.15 (14)	C6—C1—C2	120.0 (2)
C8—N1—H1	106.4	C5—C4—C3	117.9 (2)
C7—N1—H1	106.4	C5—C4—C7	120.5 (2)
Cu1—N1—H1	106.4	C3—C4—C7	121.5 (2)
C8—C10—H10A	109.5	C1—C2—C3	119.5 (2)
C8—C10—H10B	109.5	C1—C2—H2	120.2
H10A—C10—H10B	109.5	C3—C2—H2	120.2
C8—C10—H10C	109.5	N1—C7—C4	113.7 (2)
H10A—C10—H10C	109.5	N1—C7—H7A	108.8
H10B—C10—H10C	109.5	C4—C7—H7A	108.8
O1—C9—O2	124.0 (2)	N1—C7—H7B	108.8
O1—C9—O2	124.0 (2)	C4—C7—H7B	108.8
O1—C9—C8	117.2 (2)	H7A—C7—H7B	107.7
O1—C9—C8	117.2 (2)	O3^v—O4—O1	88.97 (8)
O2—C9—C8	118.8 (2)	O3^v—O4—H9	97 (3)
N1—C8—C10	111.9 (2)	O1—O4—H4	94 (3)
N1—C8—C9	111.16 (18)	H9—O4—H4	103 (4)

Symmetry codes: (i) −x, −y+1, −z; (ii) −x, y+1/2, −z+1/2; (iii) x, −y+3/2, z−1/2; (iv) x+1, −y+3/2, z+1/2; (v) −x+1, y−1/2, −z+1/2.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3···O5^iv	0.83 (4)	1.80 (4)	2.611 (3)	167 (3)
O5—H7···O1^iii	0.76 (3)	1.96 (3)	2.714 (3)	168 (3)
O5—H10···O4^ii	0.82 (4)	1.83 (4)	2.639 (3)	169 (3)
O4—H4···O3^v	0.74 (4)	1.97 (4)	2.714 (3)	172 (4)
O4—H9···O1	0.88 (4)	1.97 (5)	2.839 (3)	168 (4)

Symmetry codes: (ii) −x, y+1/2, −z+1/2; (iii) x, −y+3/2, z−1/2; (iv) x+1, −y+3/2, z+1/2; (v) −x+1, y−1/2, −z+1/2.