Chloro(2-{[5-(2-hydroxy­benzyl-O)-1,5-di­aza-1-cyclo­octyl-N,N′]­methyl}phenolato-O)­cadmium(II)

The crystal structure of the title complex, [Cd(C₂₀H₂₅­N₂­O₂)­Cl], reveals a hydrogen-bonded dimer composed of neutral molecules. The Cd^II center is five-coordinated by two O atoms of the pendant arms, two nitro­gen donors of the 1,5-di­aza­cyclo­octane ring and a chloride anion. The coordination geometry of the complex could be described as a distorted square pyramid. The 1,5-di­aza­cyclo­octane backbone adopts a boat/chair configuration and the two phenol/phenolato groups have a dihedral angle of 101.3 (2)° between them. The coordinated phenolate and phenolic groups of inversion-related mol­ecules form strong intermolecular O—H...O hydrogen bonds.

Computing details

Data collection: SMART1000 Software (Bruker, 1998); cell refinement: SMART1000 Software; data reduction: SAINT (Bruker, 1998); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXS97; molecular graphics: XP in SHELXTL (Siemens, 1996).

[Chloro-(1,5-bis(2-hydroxybenzyl)-1,5-diazacyclooctane) cadmium(II)]

Crystal data

[Cd(C20H25N2O2)Cl]	F(000) = 960
Mr = 473.27	Dx = 1.592 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 10.7364 (11) Å	Cell parameters from 3450 reflections
b = 14.0507 (13) Å	θ = 2.0–26.4°
c = 13.5546 (13) Å	µ = 1.26 mm^−1
β = 105.104 (2)°	T = 298 K
V = 1974.1 (3) Å^3	Prism, colorless
Z = 4	0.25 × 0.20 × 0.15 mm

Data collection

BRUKER SMART 1000 diffractometer	2866 reflections with I > 2.0σ(I)
ω scans	Rint = 0.042
Absorption correction: integration (North et al., 1968)	θmax = 26.4°
Tmin = 0.744, Tmax = 0.885	h = −12→13
9248 measured reflections	k = −17→17
4048 independent reflections	l = −16→8

Refinement

Refinement on F^2	Calc. w = 1/[σ^2(Fo^2) + (0.0274P)^2] P = (Fo^2 + 2Fc^2)/3
R[F^2 > 2σ(F^2)] = 0.033	(Δ/σ)max = 0.013
wR(F^2) = 0.061	Δρmax = 0.54 e Å^−3
S = 0.94	Δρmin = −0.68 e Å^−3
4048 reflections	Extinction correction: SHELXL
239 parameters	Extinction coefficient: 0.000 (2)
H-atom parameters constrained

Special details

Refinement. Full-MATRIX

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

	x	y	z	Uiso*/Ueq
Cd1	0.37687 (2)	0.128866 (16)	0.079493 (18)	0.03403 (9)
Cl1	0.40651 (12)	0.04902 (7)	0.24262 (8)	0.0676 (3)
O1	0.5672 (2)	0.12613 (16)	0.04044 (18)	0.0409 (6)
N2	0.1657 (3)	0.19108 (18)	0.0330 (2)	0.0351 (7)
O2	0.3015 (2)	0.01517 (15)	−0.03674 (18)	0.0430 (6)
C21	0.0831 (3)	0.0648 (2)	−0.1026 (3)	0.0378 (8)
C23	0.1864 (4)	−0.0352 (2)	−0.2025 (3)	0.0457 (9)
H23A	0.2590	−0.0678	−0.2097	0.055*
C6	0.1426 (4)	0.2238 (2)	0.1315 (3)	0.0455 (9)
H6A	0.1654	0.1724	0.1807	0.055*
H6B	0.0510	0.2358	0.1205	0.055*
C24	0.0739 (4)	−0.0375 (3)	−0.2806 (3)	0.0534 (10)
H24A	0.0705	−0.0728	−0.3393	0.064*
C5	0.2157 (4)	0.3126 (2)	0.1780 (3)	0.0485 (10)
H5A	0.1866	0.3649	0.1309	0.058*
H5B	0.1907	0.3274	0.2401	0.058*
C4	0.3608 (4)	0.3102 (3)	0.2038 (3)	0.0451 (9)
H4A	0.3935	0.3708	0.2340	0.054*
H4B	0.3912	0.2614	0.2551	0.054*
C20	0.0772 (3)	0.1097 (2)	−0.0031 (3)	0.0428 (9)
H20A	−0.0104	0.1313	−0.0099	0.051*
H20B	0.0956	0.0609	0.0494	0.051*
C26	−0.0273 (4)	0.0631 (3)	−0.1843 (3)	0.0504 (10)
H26A	−0.0996	0.0974	−0.1795	0.060*
C25	−0.0320 (4)	0.0120 (3)	−0.2720 (3)	0.0550 (11)
H25A	−0.1071	0.0112	−0.3250	0.066*
C22	0.1918 (3)	0.0151 (2)	−0.1139 (3)	0.0359 (8)
N1	0.4167 (3)	0.29114 (17)	0.1155 (2)	0.0360 (7)
C12	0.6295 (3)	0.2036 (2)	0.0172 (3)	0.0360 (8)
C11	0.6276 (3)	0.2892 (2)	0.0699 (3)	0.0402 (9)
C10	0.5591 (4)	0.2987 (2)	0.1526 (3)	0.0441 (9)
H10A	0.5901	0.2495	0.2033	0.053*
H10B	0.5808	0.3598	0.1859	0.053*
C1	0.3628 (4)	0.3574 (2)	0.0285 (3)	0.0431 (9)
H1A	0.4332	0.3842	0.0049	0.052*
H1B	0.3191	0.4095	0.0526	0.052*
C3	0.1444 (3)	0.2686 (2)	−0.0440 (3)	0.0424 (9)
H3A	0.0967	0.3195	−0.0222	0.051*
H3B	0.0920	0.2443	−0.1085	0.051*
C2	0.2687 (4)	0.3090 (2)	−0.0606 (3)	0.0438 (9)
H2A	0.3143	0.2574	−0.0835	0.053*
H2B	0.2455	0.3546	−0.1161	0.053*
C13	0.6936 (4)	0.1982 (3)	−0.0598 (3)	0.0446 (9)
H13A	0.6939	0.1415	−0.0951	0.054*
C16	0.6918 (4)	0.3665 (3)	0.0425 (3)	0.0591 (11)
H16A	0.6918	0.4239	0.0766	0.071*
C15	0.7556 (4)	0.3613 (3)	−0.0332 (4)	0.0694 (13)
H15A	0.7974	0.4144	−0.0500	0.083*
C14	0.7566 (4)	0.2769 (3)	−0.0835 (3)	0.0563 (11)
H14A	0.8004	0.2726	−0.1343	0.068*
H20	0.381 (4)	−0.054 (3)	−0.044 (3)	0.094 (15)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cd1	0.04057 (15)	0.02581 (12)	0.03723 (14)	0.00554 (12)	0.01287 (10)	0.00167 (12)
Cl1	0.1062 (10)	0.0500 (6)	0.0508 (6)	0.0191 (6)	0.0280 (6)	0.0213 (5)
O1	0.0407 (14)	0.0259 (12)	0.0606 (16)	0.0027 (11)	0.0210 (11)	−0.0048 (12)
N2	0.0414 (18)	0.0314 (15)	0.0382 (17)	0.0065 (13)	0.0204 (13)	0.0032 (13)
O2	0.0393 (15)	0.0332 (13)	0.0521 (16)	0.0083 (11)	0.0039 (12)	−0.0125 (11)
C21	0.036 (2)	0.0336 (18)	0.047 (2)	−0.0033 (15)	0.0170 (17)	0.0000 (16)
C23	0.045 (2)	0.040 (2)	0.054 (2)	0.0001 (17)	0.0149 (19)	−0.0094 (18)
C6	0.053 (2)	0.045 (2)	0.047 (2)	0.0114 (18)	0.0283 (19)	−0.0004 (18)
C24	0.056 (3)	0.055 (2)	0.047 (2)	−0.005 (2)	0.009 (2)	−0.010 (2)
C5	0.067 (3)	0.042 (2)	0.043 (2)	0.0102 (19)	0.028 (2)	−0.0070 (18)
C4	0.061 (3)	0.040 (2)	0.039 (2)	0.0047 (18)	0.0217 (19)	−0.0065 (17)
C20	0.038 (2)	0.043 (2)	0.054 (2)	0.0023 (16)	0.0227 (17)	0.0007 (17)
C26	0.035 (2)	0.048 (2)	0.069 (3)	−0.0019 (17)	0.014 (2)	−0.001 (2)
C25	0.044 (3)	0.062 (3)	0.051 (3)	−0.005 (2)	−0.0013 (19)	−0.001 (2)
C22	0.036 (2)	0.0259 (17)	0.046 (2)	−0.0049 (15)	0.0112 (17)	0.0023 (16)
N1	0.0466 (19)	0.0277 (15)	0.0361 (16)	0.0039 (13)	0.0149 (13)	−0.0030 (12)
C12	0.031 (2)	0.0347 (19)	0.040 (2)	0.0050 (15)	0.0048 (16)	0.0010 (16)
C11	0.038 (2)	0.0342 (19)	0.048 (2)	−0.0036 (16)	0.0097 (17)	−0.0071 (17)
C10	0.051 (2)	0.0339 (19)	0.045 (2)	−0.0015 (17)	0.0085 (18)	−0.0126 (17)
C1	0.053 (2)	0.0318 (19)	0.049 (2)	0.0063 (17)	0.0203 (17)	0.0048 (17)
C3	0.046 (2)	0.0386 (19)	0.043 (2)	0.0109 (17)	0.0135 (18)	0.0030 (17)
C2	0.058 (3)	0.037 (2)	0.039 (2)	0.0090 (18)	0.0175 (18)	0.0147 (17)
C13	0.044 (2)	0.043 (2)	0.049 (2)	0.0032 (18)	0.0154 (18)	−0.0065 (18)
C16	0.058 (3)	0.040 (2)	0.084 (3)	−0.009 (2)	0.026 (2)	−0.020 (2)
C15	0.068 (3)	0.051 (3)	0.102 (4)	−0.014 (2)	0.045 (3)	−0.002 (3)
C14	0.054 (3)	0.057 (3)	0.067 (3)	0.001 (2)	0.033 (2)	0.002 (2)

Geometric parameters (Å, º)

Cd1—O1	2.241 (2)	C24—C25	1.363 (5)
Cd1—O2	2.242 (2)	C5—C4	1.505 (5)
Cd1—N1	2.347 (3)	C4—N1	1.497 (4)
Cd1—N2	2.357 (3)	C26—C25	1.378 (5)
Cd1—Cl1	2.4253 (10)	N1—C10	1.484 (4)
O1—C12	1.357 (4)	N1—C1	1.496 (4)
N2—C3	1.484 (4)	C12—C13	1.394 (5)
N2—C20	1.485 (4)	C12—C11	1.401 (4)
N2—C6	1.492 (4)	C11—C16	1.388 (5)
O2—C22	1.356 (4)	C11—C10	1.498 (5)
C21—C26	1.396 (5)	C1—C2	1.518 (5)
C21—C22	1.402 (5)	C3—C2	1.520 (5)
C21—C20	1.505 (5)	C13—C14	1.377 (5)
C23—C22	1.382 (4)	C16—C15	1.376 (6)
C23—C24	1.384 (5)	C15—C14	1.370 (5)
C6—C5	1.521 (5)
O1—Cd1—O2	90.35 (8)	N2—C20—C21	116.4 (3)
O1—Cd1—N1	86.43 (9)	C25—C26—C21	121.7 (4)
O2—Cd1—N1	148.33 (9)	C24—C25—C26	119.8 (4)
O1—Cd1—N2	144.70 (9)	O2—C22—C23	120.1 (3)
O2—Cd1—N2	86.02 (9)	O2—C22—C21	119.7 (3)
N1—Cd1—N2	78.80 (9)	C23—C22—C21	120.2 (3)
O1—Cd1—Cl1	107.24 (7)	C10—N1—C1	112.1 (3)
O2—Cd1—Cl1	104.40 (7)	C10—N1—C4	108.0 (3)
N1—Cd1—Cl1	106.64 (7)	C1—N1—C4	111.5 (3)
N2—Cd1—Cl1	107.67 (7)	C10—N1—Cd1	104.81 (19)
C12—O1—Cd1	125.2 (2)	C1—N1—Cd1	115.40 (19)
C3—N2—C20	111.4 (3)	C4—N1—Cd1	104.5 (2)
C3—N2—C6	111.8 (2)	O1—C12—C13	120.0 (3)
C20—N2—C6	106.9 (3)	O1—C12—C11	119.7 (3)
C3—N2—Cd1	114.9 (2)	C13—C12—C11	120.2 (3)
C20—N2—Cd1	106.89 (19)	C16—C11—C12	117.4 (3)
C6—N2—Cd1	104.4 (2)	C16—C11—C10	120.3 (3)
C22—O2—Cd1	128.66 (19)	C12—C11—C10	122.2 (3)
C26—C21—C22	117.6 (3)	N1—C10—C11	113.8 (3)
C26—C21—C20	119.6 (3)	N1—C1—C2	112.8 (3)
C22—C21—C20	122.5 (3)	N2—C3—C2	113.5 (3)
C22—C23—C24	120.5 (4)	C1—C2—C3	118.5 (3)
N2—C6—C5	115.8 (3)	C14—C13—C12	120.0 (3)
C25—C24—C23	120.2 (4)	C15—C16—C11	122.5 (4)
C4—C5—C6	118.0 (3)	C14—C15—C16	119.2 (4)
N1—C4—C5	115.1 (3)	C15—C14—C13	120.7 (4)