Crystal structure of bis­{2-[bis­(2-hy­droxy­eth­yl)amino]­ethanol-κ4O,N,O′,O′′}cadmium terephthalate

Li, Y.-P.; Han, L.-Y.; Ming, J.; Su, G.-F.

doi:10.1107/S1600536814022375

metal-organic compounds

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Volume 70| Part 11| November 2014| Page m371

doi:10.1107/S1600536814022375

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Crystal structure of bis{2-[bis(2-hydroxyethyl)amino]ethanol-κ⁴O,N,O′,O′′}cadmium terephthalate

Ya-Ping Li,^a Li-Ying Han,^b ^* Julia Ming ^c and Guan-Fang Su ^a

^aDepartment of Ophthalmology, The Second Hospital of Jilin University, 218 Ziqiang Street, Changchun 130041, People's Republic of China, ^bDepartment of Gynaecology, The Second Hospital of Jilin University, 218 Ziqiang Street, Changchun 130041, People's Republic of China, and ^cSt Erik's Eye Hospital, Karolinska Institutet, Polhemsgatan 50, SE-112 82 Stockholm, Sweden
^*Correspondence e-mail: drhanly@163.com

Edited by M. Weil, Vienna University of Technology, Austria (Received 29 September 2014; accepted 11 October 2014; online 18 October 2014)

In the title salt, [Cd(C₆H₁₅NO₃)₂](C₈H₄O₄), the Cd²⁺ cation is coordinated by six O atoms and two N atoms from two tetradentate 2-[bis(2-hydroxyethyl)amino]ethanol ligands, displaying a distorted square-antiprismatic coordination. The terephthalate dianion does not coordinate to the cation but is connected through O⋯H—O hydrogen bonds of medium strength to the complex cations, leading to a layered structure extending parallel to (100).

Keywords: crystal structure; cadmium complex; terephthalate; hydrogen bonding.

CCDC reference: 1028647

1. Related literature

For Cd—O and Cd—N bond lengths resulting from CdN₂O₆ and CdN₄O₄ coordination sets, see: Shirvan & Dezfuli (2012 ); Shi & Tiekink (2009 ).

2. Experimental

2.1. Crystal data

[Cd(C₆H₁₅NO₃)₂](C₈H₄O₄)
M_r = 574.89
Orthorhombic, P b c a
a = 13.2789 (12) Å
b = 14.6329 (14) Å
c = 24.278 (2) Å
V = 4717.4 (8) Å³
Z = 8
Mo Kα radiation
μ = 0.98 mm⁻¹
T = 296 K
0.28 × 0.25 × 0.24 mm

2.2. Data collection

Bruker APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2002 ) T_min = 0.725, T_max = 0.812
28314 measured reflections
4639 independent reflections
2694 reflections with I > 2σ(I)
R_int = 0.093

2.3. Refinement

R[F² > 2σ(F²)] = 0.037
wR(F²) = 0.099
S = 0.98
4639 reflections
316 parameters
6 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.77 e Å⁻³
Δρ_min = −0.50 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O6—H01⋯O4	0.84 (2)	1.86 (2)	2.692 (4)	168 (5)
O8—H02⋯O2ⁱ	0.83 (2)	1.79 (2)	2.612 (4)	170 (5)
O5—H03⋯O4ⁱⁱ	0.84 (2)	1.82 (2)	2.645 (5)	170 (6)
O9—H04⋯O1ⁱ	0.84 (2)	1.84 (2)	2.673 (4)	169 (5)
O10—H05⋯O1ⁱⁱⁱ	0.84 (2)	1.82 (2)	2.647 (4)	169 (6)
O7—H06⋯O3	0.86 (2)	1.78 (2)	2.635 (4)	171 (5)
Symmetry codes: (i) $[x, -y-{\script{1\over 2}}, z-{\script{1\over 2}}]$ ; (ii) $[-x+{\script{1\over 2}}, y+{\script{1\over 2}}, z]$ ; (iii) $[-x+{\script{1\over 2}}, -y, z-{\script{1\over 2}}]$ .

Data collection: APEX2 (Bruker, 2002); cell refinement: SAINT (Bruker, 2002); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL97 (Sheldrick, 2008); software used to prepare material for publication: SHELXTL and publCIF (Westrip, 2010 ).

Supporting information

CCDC reference: 1028647

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536814022375/wm5070sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536814022375/wm5070Isup2.hkl

checkCIF report

Preparation top

The synthesis was performed under hydrothermal conditions. A mixture of Cd(CH₃COO)₂·2H₂O, (0.2 mmol, 0.053 g), [tris(2-hydroxyethyl)amino]ethanol (0.4 mmol, 0.062 g), sodium terephthalate (0.2 mmol, 0.042 g) and water (20 ml) in a 30 ml stainless steel reactor with a Teflon liner was heated from 293 to 433 K in 2 h and a constant temperature was maintained at 433 K for 72 h, after which the mixture was cooled to 298 K. Colorless crystals of the title compound were recovered from the resulting reaction solution.

Refinement top

The C—H H atoms were positioned with idealized geometry and refined with U_iso(H) = 1.2U_eq(C) using a riding model. The hydroxy H-atoms were located in a difference Fourier map and were refined with an O—H distance restrained to 0.85 (1) Å and with U_iso(H) = 1.5U_eq(O). One reflection (002) was obstracted from the beamstop and was omitted from the refinement.

Related literature top

For Cd—O and Cd—N bond lengths resulting from CdN₂O₆ and CdN₄O₄ coordination sets, see: Shirvan & Dezfuli (2012); Shi & Tiekink (2009).

Computing details top

Data collection: APEX2 (Bruker, 2002); cell refinement: SAINT (Bruker, 2002); data reduction: SAINT (Bruker, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008) and publCIF (Westrip, 2010).

Figures top

The molecular components of the title compound with displacement ellipsoids drawn at the 30% probability level.

The packing of the molecular components in the crystal structure of the title compound. O—H···O hydrogen bonds are indicated by dashed lines.

Bis{2-[bis(2-hydroxyethyl)amino]ethanol-κ⁴O,N,O',O''}cadmium terephthalate top

Crystal data top

[Cd(C₆H₁₅NO₃)₂](C₈H₄O₄)	F(000) = 2368
M_r = 574.89	D_x = 1.619 Mg m⁻³
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 4657 reflections
a = 13.2789 (12) Å	θ = 1.7–22.8°
b = 14.6329 (14) Å	µ = 0.98 mm⁻¹
c = 24.278 (2) Å	T = 296 K
V = 4717.4 (8) Å³	Block, colorless
Z = 8	0.28 × 0.25 × 0.24 mm

Data collection top

Bruker APEXII CCD diffractometer	4639 independent reflections
Radiation source: fine-focus sealed tube	2694 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.093
ϕ and ω scans	θ_max = 26.0°, θ_min = 2.2°
Absorption correction: multi-scan (SADABS; Bruker, 2002)	h = −16→15
T_min = 0.725, T_max = 0.812	k = −17→18
28314 measured reflections	l = −29→29

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.037	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.099	H atoms treated by a mixture of independent and constrained refinement
S = 0.98	w = 1/[σ²(F_o²) + (0.0439P)² + 0.0385P] where P = (F_o² + 2F_c²)/3
4639 reflections	(Δ/σ)_max = 0.001
316 parameters	Δρ_max = 0.77 e Å⁻³
6 restraints	Δρ_min = −0.50 e Å⁻³

Crystal data top

[Cd(C₆H₁₅NO₃)₂](C₈H₄O₄)	V = 4717.4 (8) Å³
M_r = 574.89	Z = 8
Orthorhombic, Pbca	Mo Kα radiation
a = 13.2789 (12) Å	µ = 0.98 mm⁻¹
b = 14.6329 (14) Å	T = 296 K
c = 24.278 (2) Å	0.28 × 0.25 × 0.24 mm

Data collection top

Bruker APEXII CCD diffractometer	4639 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2002)	2694 reflections with I > 2σ(I)
T_min = 0.725, T_max = 0.812	R_int = 0.093
28314 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.037	6 restraints
wR(F²) = 0.099	H atoms treated by a mixture of independent and constrained refinement
S = 0.98	Δρ_max = 0.77 e Å⁻³
4639 reflections	Δρ_min = −0.50 e Å⁻³
316 parameters

Special details top

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.

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 > 2sigma(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 (Å²) top

	x	y	z	U_iso*/U_eq
C1	0.2024 (3)	−0.1259 (3)	0.77515 (18)	0.0269 (10)
C2	0.2153 (3)	−0.1917 (3)	0.82266 (18)	0.0229 (10)
C3	0.2323 (3)	−0.2840 (3)	0.81455 (17)	0.0232 (10)
H3	0.2355	−0.3067	0.7788	0.028*
C4	0.2447 (3)	−0.3434 (3)	0.85847 (17)	0.0214 (8)
H4	0.2562	−0.4052	0.8520	0.026*
C5	0.2400 (3)	−0.3108 (3)	0.91230 (18)	0.0216 (9)
C6	0.2230 (3)	−0.2185 (3)	0.92059 (18)	0.0251 (10)
H6	0.2196	−0.1959	0.9563	0.030*
C7	0.2110 (3)	−0.1594 (3)	0.87684 (17)	0.0274 (10)
H7	0.1999	−0.0976	0.8834	0.033*
C8	0.2551 (3)	−0.3762 (3)	0.95972 (16)	0.0250 (9)
C9	0.1119 (4)	0.2604 (3)	0.6575 (2)	0.0433 (13)
H9A	0.1278	0.2958	0.6248	0.052*
H9B	0.0880	0.3017	0.6859	0.052*
C10	0.0344 (4)	0.1908 (3)	0.6448 (2)	0.0474 (14)
H10A	0.0152	0.1600	0.6786	0.057*
H10B	−0.0249	0.2210	0.6303	0.057*
C11	0.0503 (3)	−0.0201 (3)	0.65781 (19)	0.0338 (12)
H11A	0.0488	0.0142	0.6920	0.041*
H11B	0.0093	−0.0745	0.6624	0.041*
C12	0.0110 (3)	0.0362 (3)	0.6121 (2)	0.0366 (13)
H12A	−0.0589	0.0512	0.6194	0.044*
H12B	0.0136	0.0011	0.5783	0.044*
C13	0.0602 (4)	0.1576 (4)	0.5480 (2)	0.0496 (15)
H13A	0.0903	0.2179	0.5463	0.060*
H13B	−0.0107	0.1640	0.5391	0.060*
C14	0.1083 (4)	0.0988 (4)	0.5058 (2)	0.0497 (15)
H14A	0.0694	0.0432	0.5011	0.060*
H14B	0.1102	0.1306	0.4708	0.060*
C15	0.3955 (4)	0.0473 (4)	0.7273 (2)	0.0451 (14)
H15A	0.4191	−0.0147	0.7216	0.054*
H15B	0.4024	0.0620	0.7661	0.054*
C16	0.4576 (4)	0.1130 (4)	0.6931 (2)	0.0430 (13)
H16A	0.4396	0.1752	0.7028	0.052*
H16B	0.5283	0.1044	0.7016	0.052*
C17	0.4911 (4)	0.0136 (3)	0.6150 (2)	0.0437 (14)
H17A	0.5602	0.0266	0.6047	0.052*
H17B	0.4922	−0.0301	0.6450	0.052*
C18	0.4374 (3)	−0.0270 (3)	0.5672 (2)	0.0416 (13)
H18A	0.4369	0.0155	0.5365	0.050*
H18B	0.4705	−0.0828	0.5555	0.050*
C19	0.4816 (4)	0.1776 (3)	0.6017 (2)	0.0502 (15)
H19A	0.5417	0.2007	0.6197	0.060*
H19B	0.5008	0.1565	0.5653	0.060*
C20	0.4083 (3)	0.2523 (3)	0.5961 (2)	0.0408 (12)
H20A	0.3934	0.2782	0.6319	0.049*
H20B	0.4355	0.3001	0.5728	0.049*
N1	0.0693 (3)	0.1224 (3)	0.60478 (15)	0.0306 (9)
N2	0.4415 (3)	0.0993 (3)	0.63382 (16)	0.0326 (9)
O1	0.2571 (2)	−0.3443 (2)	1.00821 (12)	0.0369 (8)
O2	0.2658 (2)	−0.4589 (2)	0.94888 (12)	0.0398 (9)
O3	0.1960 (3)	−0.0423 (2)	0.78535 (12)	0.0408 (9)
O4	0.1988 (3)	−0.1589 (2)	0.72712 (12)	0.0346 (8)
O5	0.1974 (3)	0.2125 (2)	0.67582 (16)	0.0522 (10)
H03	0.236 (4)	0.251 (3)	0.690 (2)	0.078*
O6	0.1506 (2)	−0.0445 (2)	0.64437 (12)	0.0270 (7)
H01	0.174 (3)	−0.080 (3)	0.6685 (15)	0.040*
O7	0.2943 (3)	0.0547 (2)	0.71137 (12)	0.0353 (8)
H06	0.257 (3)	0.026 (3)	0.7342 (17)	0.053*
O8	0.2064 (3)	0.0772 (2)	0.52263 (13)	0.0342 (8)
H02	0.226 (3)	0.035 (3)	0.5023 (18)	0.051*
O9	0.3366 (2)	−0.0460 (2)	0.58471 (12)	0.0314 (8)
H04	0.304 (3)	−0.078 (3)	0.5619 (16)	0.047*
O10	0.3200 (3)	0.2158 (2)	0.57235 (16)	0.0534 (11)
H05	0.289 (4)	0.255 (3)	0.554 (2)	0.080*
Cd1	0.25186 (2)	0.085556 (19)	0.618765 (11)	0.02039 (10)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.024 (2)	0.034 (3)	0.023 (3)	0.002 (2)	0.004 (2)	0.003 (2)
C2	0.019 (2)	0.027 (3)	0.022 (2)	−0.0035 (17)	0.0035 (18)	0.0032 (19)
C3	0.025 (3)	0.027 (2)	0.017 (2)	−0.0013 (18)	−0.0014 (18)	−0.0037 (18)
C4	0.0197 (19)	0.020 (2)	0.025 (2)	−0.001 (2)	0.000 (2)	−0.0003 (18)
C5	0.015 (2)	0.027 (2)	0.022 (2)	−0.0026 (19)	0.003 (2)	−0.0009 (17)
C6	0.031 (3)	0.028 (3)	0.016 (2)	−0.0021 (18)	0.0010 (18)	−0.0038 (18)
C7	0.029 (2)	0.023 (2)	0.031 (3)	0.0015 (19)	0.004 (2)	−0.004 (2)
C8	0.024 (2)	0.030 (2)	0.021 (2)	0.003 (2)	0.000 (2)	0.0019 (19)
C9	0.042 (3)	0.031 (3)	0.057 (4)	0.008 (2)	−0.005 (3)	0.000 (3)
C10	0.036 (3)	0.034 (3)	0.073 (4)	0.005 (2)	0.012 (3)	−0.005 (3)
C11	0.030 (3)	0.037 (3)	0.035 (3)	−0.002 (2)	0.012 (2)	0.001 (2)
C12	0.019 (2)	0.042 (3)	0.049 (3)	−0.006 (2)	0.000 (2)	−0.002 (3)
C13	0.028 (3)	0.069 (4)	0.052 (4)	0.009 (3)	−0.002 (3)	0.032 (3)
C14	0.034 (3)	0.086 (4)	0.029 (3)	−0.017 (3)	−0.007 (2)	0.008 (3)
C15	0.051 (3)	0.053 (3)	0.032 (3)	0.008 (3)	−0.016 (3)	0.001 (3)
C16	0.036 (3)	0.046 (3)	0.047 (3)	0.002 (2)	−0.019 (3)	−0.008 (3)
C17	0.024 (3)	0.046 (3)	0.062 (4)	0.002 (2)	0.009 (2)	−0.003 (3)
C18	0.029 (3)	0.049 (3)	0.047 (3)	0.004 (2)	0.019 (2)	−0.003 (3)
C19	0.033 (3)	0.041 (3)	0.077 (4)	−0.008 (2)	0.007 (3)	0.007 (3)
C20	0.034 (3)	0.032 (3)	0.056 (3)	−0.008 (2)	−0.003 (2)	0.000 (3)
N1	0.028 (2)	0.031 (2)	0.033 (2)	0.0069 (17)	0.0026 (18)	0.0043 (18)
N2	0.024 (2)	0.031 (2)	0.043 (3)	−0.0033 (17)	−0.0015 (18)	0.0016 (19)
O1	0.059 (2)	0.0299 (17)	0.0212 (16)	0.0052 (17)	0.0000 (17)	0.0011 (13)
O2	0.073 (3)	0.0216 (17)	0.0246 (17)	0.0099 (17)	0.0092 (16)	0.0015 (14)
O3	0.071 (2)	0.0246 (19)	0.0265 (19)	0.0041 (17)	0.0081 (17)	0.0015 (15)
O4	0.052 (2)	0.0309 (19)	0.0208 (17)	0.0054 (16)	−0.0057 (16)	0.0014 (15)
O5	0.049 (2)	0.046 (2)	0.061 (3)	0.0186 (19)	−0.025 (2)	−0.019 (2)
O6	0.0220 (17)	0.0293 (18)	0.0296 (19)	0.0016 (13)	0.0023 (14)	0.0040 (15)
O7	0.0362 (19)	0.041 (2)	0.029 (2)	−0.0052 (16)	−0.0096 (15)	0.0083 (16)
O8	0.0411 (19)	0.035 (2)	0.0263 (19)	0.0046 (16)	−0.0084 (16)	−0.0061 (15)
O9	0.0274 (19)	0.039 (2)	0.0273 (19)	0.0003 (15)	0.0012 (14)	−0.0075 (15)
O10	0.049 (2)	0.046 (2)	0.065 (3)	−0.0230 (19)	−0.030 (2)	0.0273 (19)
Cd1	0.01904 (16)	0.02366 (17)	0.01848 (16)	−0.00051 (15)	−0.00175 (15)	0.00114 (13)

Geometric parameters (Å, º) top

C1—O3	1.250 (5)	C14—H14B	0.9700
C1—O4	1.263 (5)	C15—O7	1.402 (5)
C1—C2	1.512 (6)	C15—C16	1.513 (7)
C2—C3	1.385 (5)	C15—H15A	0.9700
C2—C7	1.398 (6)	C15—H15B	0.9700
C3—C4	1.385 (5)	C16—N2	1.469 (6)
C3—H3	0.9300	C16—H16A	0.9700
C4—C5	1.393 (6)	C16—H16B	0.9700
C4—H4	0.9300	C17—C18	1.486 (6)
C5—C6	1.384 (5)	C17—N2	1.488 (5)
C5—C8	1.511 (6)	C17—H17A	0.9700
C6—C7	1.378 (6)	C17—H17B	0.9700
C6—H6	0.9300	C18—O9	1.432 (5)
C7—H7	0.9300	C18—H18A	0.9700
C8—O2	1.246 (5)	C18—H18B	0.9700
C8—O1	1.267 (5)	C19—C20	1.469 (6)
C9—O5	1.407 (5)	C19—N2	1.485 (6)
C9—C10	1.480 (6)	C19—H19A	0.9700
C9—H9A	0.9700	C19—H19B	0.9700
C9—H9B	0.9700	C20—O10	1.412 (5)
C10—N1	1.470 (6)	C20—H20A	0.9700
C10—H10A	0.9700	C20—H20B	0.9700
C10—H10B	0.9700	N1—Cd1	2.506 (4)
C11—O6	1.417 (5)	N2—Cd1	2.553 (4)
C11—C12	1.477 (6)	O5—Cd1	2.427 (3)
C11—H11A	0.9700	O5—H03	0.84 (2)
C11—H11B	0.9700	O6—Cd1	2.412 (3)
C12—N1	1.490 (6)	O6—H01	0.841 (19)
C12—H12A	0.9700	O7—Cd1	2.362 (3)
C12—H12B	0.9700	O7—H06	0.859 (19)
C13—N1	1.477 (6)	O8—Cd1	2.414 (3)
C13—C14	1.481 (7)	O8—H02	0.831 (19)
C13—H13A	0.9700	O9—Cd1	2.378 (3)
C13—H13B	0.9700	O9—H04	0.841 (19)
C14—O8	1.402 (6)	O10—Cd1	2.392 (3)
C14—H14A	0.9700	O10—H05	0.84 (2)

O3—C1—O4	123.7 (4)	H17A—C17—H17B	108.0
O3—C1—C2	118.6 (4)	O9—C18—C17	107.1 (4)
O4—C1—C2	117.7 (4)	O9—C18—H18A	110.3
C3—C2—C7	118.0 (4)	C17—C18—H18A	110.3
C3—C2—C1	122.1 (4)	O9—C18—H18B	110.3
C7—C2—C1	119.9 (4)	C17—C18—H18B	110.3
C4—C3—C2	121.5 (4)	H18A—C18—H18B	108.5
C4—C3—H3	119.3	C20—C19—N2	112.6 (4)
C2—C3—H3	119.3	C20—C19—H19A	109.1
C3—C4—C5	120.1 (4)	N2—C19—H19A	109.1
C3—C4—H4	119.9	C20—C19—H19B	109.1
C5—C4—H4	119.9	N2—C19—H19B	109.1
C6—C5—C4	118.6 (4)	H19A—C19—H19B	107.8
C6—C5—C8	122.0 (4)	O10—C20—C19	107.9 (4)
C4—C5—C8	119.4 (4)	O10—C20—H20A	110.1
C7—C6—C5	121.2 (4)	C19—C20—H20A	110.1
C7—C6—H6	119.4	O10—C20—H20B	110.1
C5—C6—H6	119.4	C19—C20—H20B	110.1
C6—C7—C2	120.6 (4)	H20A—C20—H20B	108.4
C6—C7—H7	119.7	C10—N1—C13	110.7 (4)
C2—C7—H7	119.7	C10—N1—C12	109.5 (4)
O2—C8—O1	123.5 (4)	C13—N1—C12	111.4 (4)
O2—C8—C5	118.0 (4)	C10—N1—Cd1	111.2 (3)
O1—C8—C5	118.4 (4)	C13—N1—Cd1	106.3 (3)
O5—C9—C10	106.5 (4)	C12—N1—Cd1	107.7 (3)
O5—C9—H9A	110.4	C16—N2—C19	111.0 (4)
C10—C9—H9A	110.4	C16—N2—C17	110.6 (4)
O5—C9—H9B	110.4	C19—N2—C17	109.3 (4)
C10—C9—H9B	110.4	C16—N2—Cd1	107.1 (3)
H9A—C9—H9B	108.6	C19—N2—Cd1	109.8 (3)
N1—C10—C9	112.8 (4)	C17—N2—Cd1	109.0 (3)
N1—C10—H10A	109.0	C9—O5—Cd1	116.2 (3)
C9—C10—H10A	109.0	C9—O5—H03	107 (4)
N1—C10—H10B	109.0	Cd1—O5—H03	124 (4)
C9—C10—H10B	109.0	C11—O6—Cd1	112.6 (2)
H10A—C10—H10B	107.8	C11—O6—H01	110 (3)
O6—C11—C12	107.4 (3)	Cd1—O6—H01	117 (3)
O6—C11—H11A	110.2	C15—O7—Cd1	120.4 (3)
C12—C11—H11A	110.2	C15—O7—H06	110 (3)
O6—C11—H11B	110.2	Cd1—O7—H06	125 (3)
C12—C11—H11B	110.2	C14—O8—Cd1	120.2 (3)
H11A—C11—H11B	108.5	C14—O8—H02	107 (3)
C11—C12—N1	112.3 (4)	Cd1—O8—H02	122 (4)
C11—C12—H12A	109.1	C18—O9—Cd1	112.8 (3)
N1—C12—H12A	109.1	C18—O9—H04	113 (4)
C11—C12—H12B	109.1	Cd1—O9—H04	116 (4)
N1—C12—H12B	109.1	C20—O10—Cd1	115.0 (3)
H12A—C12—H12B	107.9	C20—O10—H05	112 (4)
N1—C13—C14	114.0 (4)	Cd1—O10—H05	127 (4)
N1—C13—H13A	108.8	O7—Cd1—O9	93.62 (11)
C14—C13—H13A	108.8	O7—Cd1—O10	120.72 (11)
N1—C13—H13B	108.8	O9—Cd1—O10	107.59 (13)
C14—C13—H13B	108.8	O7—Cd1—O6	74.73 (10)
H13A—C13—H13B	107.6	O9—Cd1—O6	73.42 (10)
O8—C14—C13	109.4 (4)	O10—Cd1—O6	163.97 (10)
O8—C14—H14A	109.8	O7—Cd1—O8	166.04 (11)
C13—C14—H14A	109.8	O9—Cd1—O8	74.99 (10)
O8—C14—H14B	109.8	O10—Cd1—O8	71.32 (12)
C13—C14—H14B	109.8	O6—Cd1—O8	93.99 (11)
H14A—C14—H14B	108.3	O7—Cd1—O5	71.00 (12)
O7—C15—C16	108.8 (4)	O9—Cd1—O5	163.50 (11)
O7—C15—H15A	109.9	O10—Cd1—O5	76.81 (14)
C16—C15—H15A	109.9	O6—Cd1—O5	106.89 (12)
O7—C15—H15B	109.9	O8—Cd1—O5	121.08 (11)
C16—C15—H15B	109.9	O7—Cd1—N1	113.65 (12)
H15A—C15—H15B	108.3	O9—Cd1—N1	125.77 (11)
N2—C16—C15	111.8 (4)	O10—Cd1—N1	97.51 (12)
N2—C16—H16A	109.3	O6—Cd1—N1	70.45 (11)
C15—C16—H16A	109.3	O8—Cd1—N1	68.78 (12)
N2—C16—H16B	109.3	O5—Cd1—N1	67.95 (12)
C15—C16—H16B	109.3	O7—Cd1—N2	69.10 (12)
H16A—C16—H16B	107.9	O9—Cd1—N2	69.32 (11)
C18—C17—N2	111.4 (4)	O10—Cd1—N2	68.38 (12)
C18—C17—H17A	109.4	O6—Cd1—N2	125.13 (11)
N2—C17—H17A	109.4	O8—Cd1—N2	112.90 (12)
C18—C17—H17B	109.4	O5—Cd1—N2	98.74 (12)
N2—C17—H17B	109.4	N1—Cd1—N2	163.06 (13)

O3—C1—C2—C3	−173.8 (4)	C20—O10—Cd1—O5	78.4 (3)
O4—C1—C2—C3	6.0 (6)	C20—O10—Cd1—N1	143.5 (3)
O3—C1—C2—C7	5.6 (6)	C20—O10—Cd1—N2	−26.8 (3)
O4—C1—C2—C7	−174.5 (4)	C11—O6—Cd1—O7	100.0 (3)
C7—C2—C3—C4	0.1 (6)	C11—O6—Cd1—O9	−161.4 (3)
C1—C2—C3—C4	179.5 (4)	C11—O6—Cd1—O10	−65.3 (5)
C2—C3—C4—C5	0.1 (6)	C11—O6—Cd1—O8	−88.4 (3)
C3—C4—C5—C6	−0.1 (6)	C11—O6—Cd1—O5	35.8 (3)
C3—C4—C5—C8	−179.2 (4)	C11—O6—Cd1—N1	−22.5 (3)
C4—C5—C6—C7	−0.1 (6)	C11—O6—Cd1—N2	149.9 (3)
C8—C5—C6—C7	179.0 (4)	C14—O8—Cd1—O7	105.2 (5)
C5—C6—C7—C2	0.3 (7)	C14—O8—Cd1—O9	141.3 (4)
C3—C2—C7—C6	−0.3 (7)	C14—O8—Cd1—O10	−103.8 (4)
C1—C2—C7—C6	−179.8 (4)	C14—O8—Cd1—O6	69.7 (3)
C6—C5—C8—O2	177.1 (4)	C14—O8—Cd1—O5	−42.8 (4)
C4—C5—C8—O2	−3.9 (6)	C14—O8—Cd1—N1	2.4 (3)
C6—C5—C8—O1	−3.6 (6)	C14—O8—Cd1—N2	−159.4 (3)
C4—C5—C8—O1	175.5 (4)	C9—O5—Cd1—O7	−149.8 (4)
O5—C9—C10—N1	−56.0 (6)	C9—O5—Cd1—O9	−171.7 (4)
O6—C11—C12—N1	−61.9 (5)	C9—O5—Cd1—O10	80.8 (3)
N1—C13—C14—O8	−49.3 (6)	C9—O5—Cd1—O6	−83.1 (3)
O7—C15—C16—N2	−53.9 (5)	C9—O5—Cd1—O8	22.5 (4)
N2—C17—C18—O9	−59.8 (5)	C9—O5—Cd1—N1	−23.1 (3)
N2—C19—C20—O10	−55.9 (6)	C9—O5—Cd1—N2	146.0 (3)
C9—C10—N1—C13	−81.6 (5)	C10—N1—Cd1—O7	48.2 (3)
C9—C10—N1—C12	155.2 (4)	C13—N1—Cd1—O7	168.8 (3)
C9—C10—N1—Cd1	36.4 (5)	C12—N1—Cd1—O7	−71.7 (3)
C14—C13—N1—C10	171.0 (4)	C10—N1—Cd1—O9	161.8 (3)
C14—C13—N1—C12	−67.0 (5)	C13—N1—Cd1—O9	−77.6 (3)
C14—C13—N1—Cd1	50.1 (5)	C12—N1—Cd1—O9	41.9 (3)
C11—C12—N1—C10	−81.3 (5)	C10—N1—Cd1—O10	−80.1 (3)
C11—C12—N1—C13	155.9 (4)	C13—N1—Cd1—O10	40.5 (3)
C11—C12—N1—Cd1	39.7 (4)	C12—N1—Cd1—O10	160.0 (3)
C15—C16—N2—C19	165.7 (4)	C10—N1—Cd1—O6	110.8 (3)
C15—C16—N2—C17	−72.8 (5)	C13—N1—Cd1—O6	−128.6 (3)
C15—C16—N2—Cd1	45.9 (4)	C12—N1—Cd1—O6	−9.1 (3)
C20—C19—N2—C16	−86.5 (5)	C10—N1—Cd1—O8	−146.6 (3)
C20—C19—N2—C17	151.3 (4)	C13—N1—Cd1—O8	−26.0 (3)
C20—C19—N2—Cd1	31.7 (5)	C12—N1—Cd1—O8	93.4 (3)
C18—C17—N2—C16	150.9 (4)	C10—N1—Cd1—O5	−7.6 (3)
C18—C17—N2—C19	−86.7 (5)	C13—N1—Cd1—O5	113.0 (3)
C18—C17—N2—Cd1	33.4 (5)	C12—N1—Cd1—O5	−127.6 (3)
C10—C9—O5—Cd1	49.1 (5)	C10—N1—Cd1—N2	−47.5 (6)
C12—C11—O6—Cd1	51.2 (4)	C13—N1—Cd1—N2	73.1 (5)
C16—C15—O7—Cd1	34.1 (5)	C12—N1—Cd1—N2	−167.5 (4)
C13—C14—O8—Cd1	22.1 (5)	C16—N2—Cd1—O7	−20.5 (3)
C17—C18—O9—Cd1	56.8 (4)	C19—N2—Cd1—O7	−141.1 (3)
C19—C20—O10—Cd1	53.3 (5)	C17—N2—Cd1—O7	99.2 (3)
C15—O7—Cd1—O9	58.4 (3)	C16—N2—Cd1—O9	−123.0 (3)
C15—O7—Cd1—O10	−54.6 (4)	C19—N2—Cd1—O9	116.4 (3)
C15—O7—Cd1—O6	130.1 (3)	C17—N2—Cd1—O9	−3.3 (3)
C15—O7—Cd1—O8	93.1 (6)	C16—N2—Cd1—O10	117.2 (3)
C15—O7—Cd1—O5	−115.5 (3)	C19—N2—Cd1—O10	−3.4 (3)
C15—O7—Cd1—N1	−169.8 (3)	C17—N2—Cd1—O10	−123.1 (3)
C15—O7—Cd1—N2	−7.8 (3)	C16—N2—Cd1—O6	−72.6 (3)
C18—O9—Cd1—O7	−94.5 (3)	C19—N2—Cd1—O6	166.8 (3)
C18—O9—Cd1—O10	29.3 (3)	C17—N2—Cd1—O6	47.1 (3)
C18—O9—Cd1—O6	−167.4 (3)	C16—N2—Cd1—O8	174.4 (3)
C18—O9—Cd1—O8	93.7 (3)	C19—N2—Cd1—O8	53.8 (3)
C18—O9—Cd1—O5	−73.8 (5)	C17—N2—Cd1—O8	−65.9 (3)
C18—O9—Cd1—N1	142.8 (3)	C16—N2—Cd1—O5	45.2 (3)
C18—O9—Cd1—N2	−28.5 (3)	C19—N2—Cd1—O5	−75.4 (3)
C20—O10—Cd1—O7	20.2 (4)	C17—N2—Cd1—O5	164.9 (3)
C20—O10—Cd1—O9	−85.1 (3)	C16—N2—Cd1—N1	82.2 (5)
C20—O10—Cd1—O6	−176.3 (4)	C19—N2—Cd1—N1	−38.4 (6)
C20—O10—Cd1—O8	−151.9 (4)	C17—N2—Cd1—N1	−158.1 (4)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O6—H01···O4	0.84 (2)	1.86 (2)	2.692 (4)	168 (5)
O8—H02···O2ⁱ	0.83 (2)	1.79 (2)	2.612 (4)	170 (5)
O5—H03···O4ⁱⁱ	0.84 (2)	1.82 (2)	2.645 (5)	170 (6)
O9—H04···O1ⁱ	0.84 (2)	1.84 (2)	2.673 (4)	169 (5)
O10—H05···O1ⁱⁱⁱ	0.84 (2)	1.82 (2)	2.647 (4)	169 (6)
O7—H06···O3	0.86 (2)	1.78 (2)	2.635 (4)	171 (5)

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O6—H01···O4	0.841 (19)	1.86 (2)	2.692 (4)	168 (5)
O8—H02···O2ⁱ	0.831 (19)	1.79 (2)	2.612 (4)	170 (5)
O5—H03···O4ⁱⁱ	0.84 (2)	1.82 (2)	2.645 (5)	170 (6)
O9—H04···O1ⁱ	0.841 (19)	1.84 (2)	2.673 (4)	169 (5)
O10—H05···O1ⁱⁱⁱ	0.84 (2)	1.82 (2)	2.647 (4)	169 (6)
O7—H06···O3	0.859 (19)	1.78 (2)	2.635 (4)	171 (5)

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

Acknowledgements

This project was supported by the International Scientific and Technological Cooperation Foundation of Jilin Province (grant No. 20120722).

References

Bruker (2002). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Shi, L.-P. & Tiekink, E. R. T. (2009). Acta Cryst. E65, m885–m886. Web of Science CSD CrossRef IUCr Journals Google Scholar
Shirvan, S. A. & Haydari Dezfuli, S. (2012). Acta Cryst. E68, m1008–m1009. CSD CrossRef IUCr Journals Google Scholar
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920–925. Web of Science CrossRef CAS IUCr Journals Google Scholar

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Volume 70| Part 11| November 2014| Page m371

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