Aqua­bis(2-iodo­acetato-κO)(1,10-phenanthroline-κ2N,N′)copper(II)

Zhao, R.; Sun, J.; Lu, J.; Li, J.

doi:10.1107/S1600536809002682

metal-organic compounds

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ISSN: 2056-9890

Volume 65| Part 2| February 2009| Page m241

doi:10.1107/S1600536809002682

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Aquabis(2-iodoacetato-κO)(1,10-phenanthroline-κ²N,N′)copper(II)

Rengao Zhao,^a Junshan Sun,^a ^* Jie Lu ^b and Jikun Li ^a

^aDepartment of Materials and Chemical Engineering, Taishan University, 271021 Taian, Shandong, People's Republic of China, and ^bDepartment of Applied and Science Technology, Taishan University, 271021 Taian, Shandong, People's Republic of China
^*Correspondence e-mail: klsz79@163.com

(Received 15 January 2009; accepted 22 January 2009; online 31 January 2009)

In the title compound, [Cu(C₂H₂IO₂)₂(C₁₂H₈N₂)(H₂O)], the Cu^II ion is coordinated by two N atoms [Cu—N = 2.013 (4) and 2.024 (4) Å] from a 1,10-phenanthroline ligand and three O atoms [Cu—O = 1.940 (4)–2.261 (4) Å] from two carboxyl ligands and a water molecule in a distorted square-pyramidal geometry. One iodoacetate O atom [Cu—O = 2.775 (4) Å] completes the coordination to form a distorted octahedron. Intermolecular O—H⋯O hydrogen bonds link the molecules into centrosymmetric dimers, which are further packed by π–π interactions between the 1,10-phenanthroline ligands into layers parallel to the ab plane. The crystal packing also exhibits short intermolecular I⋯I contacts of 3.6772 (9) Å and weak C—H⋯O hydrogen bonds.

Related literature

The related crystal structure of aquabis(2,4-dichlorophenoxyacetato-O)(1,10-phenanthroline-κ²N,N′)copper(II) has been reported by Liu et al. (2006 ).

Experimental

Crystal data

[Cu(C₂H₂IO₂)₂(C₁₂H₈N₂)(H₂O)]
M_r = 631.63
Triclinic, $[P \overline 1]$
a = 9.5156 (11) Å
b = 10.6293 (12) Å
c = 11.3441 (13) Å
α = 65.803 (2)°
β = 65.598 (2)°
γ = 72.451 (2)°
V = 940.94 (19) Å³
Z = 2
Mo Kα radiation
μ = 4.47 mm⁻¹
T = 273 (2) K
0.26 × 0.23 × 0.21 mm

Data collection

Bruker SMART APEX diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.389, T_max = 0.454 (expected range = 0.336–0.391)
4948 measured reflections
3305 independent reflections
2934 reflections with I > 2σ(I)
R_int = 0.016

Refinement

R[F² > 2σ(F²)] = 0.038
wR(F²) = 0.104
S = 1.01
3305 reflections
237 parameters
3 restraints
H-atom parameters constrained
Δρ_max = 1.53 e Å⁻³
Δρ_min = −1.68 e Å⁻³

Table 1
Selected interatomic distances (Å)

Cg1, Cg2 and Cg3 are the centroids of the C4–C7/C11/C12, C6–C10/N2 and C1–C5/N1 rings, respectively.

Cg1⋯Cg3ⁱ	3.505 (6)
Cg1⋯Cg1ⁱⁱ	3.584 (6)
Cg2⋯Cg3ⁱ	3.625 (6)
Cg2⋯Cg1ⁱⁱ	3.634 (6)
I2⋯I2ⁱⁱⁱ	3.6772 (9)
Symmetry codes: (i) -x+2, -y+2, -z; (ii) -x+1, -y+2, -z; (iii) -x+1, -y, -z+1.

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1B⋯O3	0.85	1.84	2.639 (6)	156
O1—H1C⋯O4^iv	0.85	1.97	2.785 (5)	161
C3—H3⋯O1ⁱⁱ	0.93	2.44	3.240 (7)	144
C11—H11⋯O5ⁱ	0.93	2.71	3.508 (8)	144
C10—H10⋯O3^iv	0.93	2.68	3.431 (8)	138
C14—H14B⋯O2^v	0.97	2.59	3.436 (8)	146
C14—H14A⋯O5^v	0.97	2.64	3.219 (8)	119
Symmetry codes: (i) -x+2, -y+2, -z; (ii) -x+1, -y+2, -z; (iv) -x+2, -y+1, -z; (v) -x+1, -y+1, -z+1.

Data collection: SMART (Siemens, 1996 ); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT; 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).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809002682/cv2511sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809002682/cv2511Isup2.hkl

checkCIF report

Comment top

Metal complexes with carboxylates are among the most investigated complexes in the field of coordination chemistry. Due to their versatile bonding modes with metal ions, they have also been used in the synthesis of mononuclear monomeric and polymeric complexes (Liu et al., 2006). In order to develop some new topological structures, we study the reaction of the copper(II) ion and 2-iodoacetic acid with the presence of 1,10-phenanthroline.

The molecular structure of the title complex is shown in Fig.1. The Cu atom exhibits a six-coordinated distorted octahedral pyramidal geometry with two carboxyl O atoms from (Cu2—O4 2.000 (4) Å, Cu2—O5 2.775 (4) Å), a water molecule (Cu—O 2.261 (4) Å) and a nitrogen atom (Cu2—N2 2.024 (4) Å) occupying the equatorial planar position. A nitrogen atom N2 (Cu2—N2 2.013 (4) Å) and a carboxyl O atom (Cu2—O2 1.940 (4) Å) occupy the apical positions. The displacement of the metal atom from the basal plane is 0.0640 (2) Å. The crystal packing exhibits short intermolecular I···I contacts (Table 1) and weak C—H···O hydrogen bonds (Table 2).

Related literature top

The related crystal structure of aquabis(2,4-dichlorophenoxyacetato-O) (1,10-phenanthroline-κ²N,N')copper(II) has been reported by Liu et al. (2006).

Experimental top

The reaction was carried out by the solvothermal method. 2-iodoacetic acid(0.372 g,2 mmol) and cupric acetate(0.199 g, 1 mmol) and 1,10-phenanthroline(0.180 g, 1 mmol) were added to the airtight vessel with 20 ml water. The resulting green solution was filtered. The filtrate was placed for sevaral days yielding blue block-shaped crystals.

The yield is 81%. Elemental analysis: calc. for C₁₆H₁₄CuI₂N₂O₅: C 30.42, H 2.23, N 4.43; found: C 30.15, H 2.49, N 4.22. The elemental analyses were performed with PERKIN ELMER MODEL 2400 SERIES II.

Computing details top

Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT (Siemens, 1996); 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).

Figures top

Fig. 1. The molecular structure of the title compound showing the atomic numbering and 30% probability displacement ellipsoids.

Aquabis(2-iodoacetato-κO)(1,10-phenanthroline- κ²N,N')copper(II) top

Crystal data top

[Cu(C₂H₂IO₂)₂(C₁₂H₈N₂)(H₂O)]	Z = 2
M_r = 631.63	F(000) = 598
Triclinic, P1	D_x = 2.229 Mg m⁻³
a = 9.5156 (11) Å	Mo Kα radiation, λ = 0.71073 Å
b = 10.6293 (12) Å	Cell parameters from 3047 reflections
c = 11.3441 (13) Å	θ = 2.6–28.1°
α = 65.803 (2)°	µ = 4.47 mm⁻¹
β = 65.598 (2)°	T = 273 K
γ = 72.451 (2)°	Block, blue
V = 940.94 (19) Å³	0.26 × 0.23 × 0.21 mm

Data collection top

Bruker APEXII diffractometer	3305 independent reflections
Radiation source: fine-focus sealed tube	2934 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.016
ϕ and ω scans	θ_max = 25.1°, θ_min = 2.1°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −11→11
T_min = 0.389, T_max = 0.454	k = −12→10
4948 measured reflections	l = −13→12

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)] = 0.038	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.104	H-atom parameters constrained
S = 1.01	w = 1/[σ²(F_o²) + (0.056P)² + 3.6149P] where P = (F_o² + 2F_c²)/3
3305 reflections	(Δ/σ)_max < 0.001
237 parameters	Δρ_max = 1.53 e Å⁻³
3 restraints	Δρ_min = −1.68 e Å⁻³

Crystal data top

[Cu(C₂H₂IO₂)₂(C₁₂H₈N₂)(H₂O)]	γ = 72.451 (2)°
M_r = 631.63	V = 940.94 (19) Å³
Triclinic, P1	Z = 2
a = 9.5156 (11) Å	Mo Kα radiation
b = 10.6293 (12) Å	µ = 4.47 mm⁻¹
c = 11.3441 (13) Å	T = 273 K
α = 65.803 (2)°	0.26 × 0.23 × 0.21 mm
β = 65.598 (2)°

Data collection top

Bruker APEXII diffractometer	3305 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	2934 reflections with I > 2σ(I)
T_min = 0.389, T_max = 0.454	R_int = 0.016
4948 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.038	3 restraints
wR(F²) = 0.104	H-atom parameters constrained
S = 1.01	Δρ_max = 1.53 e Å⁻³
3305 reflections	Δρ_min = −1.68 e Å⁻³
237 parameters

Special details top

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 (Å²) top

	x	y	z	U_iso*/U_eq
Cu2	0.76967 (7)	0.67482 (6)	0.13753 (6)	0.02670 (17)
I1	0.95532 (7)	0.21497 (5)	0.43653 (6)	0.06644 (19)
I2	0.43146 (5)	0.18948 (4)	0.45215 (4)	0.04345 (15)
N1	0.6118 (5)	0.8490 (4)	0.1546 (4)	0.0255 (9)
N2	0.9024 (5)	0.8189 (4)	−0.0095 (4)	0.0280 (9)
O1	0.7777 (4)	0.6019 (4)	−0.0268 (4)	0.0341 (9)
H1C	0.8711	0.5671	−0.0635	0.031 (15)*
H1B	0.7272	0.5340	0.0231	0.06 (2)*
O2	0.6142 (4)	0.5607 (4)	0.2794 (4)	0.0359 (9)
O3	0.6083 (7)	0.4189 (6)	0.1825 (5)	0.0661 (15)
O4	0.9474 (4)	0.5270 (4)	0.1793 (4)	0.0329 (8)
O5	0.8852 (5)	0.6118 (4)	0.3468 (4)	0.0429 (10)
C1	0.4672 (6)	0.8592 (6)	0.2411 (5)	0.0307 (11)
H1A	0.4265	0.7782	0.3029	0.037*
C2	0.3740 (7)	0.9891 (6)	0.2417 (6)	0.0382 (13)
H2	0.2725	0.9934	0.3032	0.046*
C3	0.4311 (7)	1.1090 (6)	0.1529 (6)	0.0382 (13)
H3	0.3693	1.1954	0.1536	0.046*
C4	0.5840 (6)	1.1012 (5)	0.0602 (6)	0.0302 (11)
C5	0.6710 (6)	0.9677 (5)	0.0657 (5)	0.0241 (10)
C6	0.8265 (6)	0.9512 (5)	−0.0244 (5)	0.0249 (10)
C7	0.8936 (6)	1.0689 (6)	−0.1235 (5)	0.0305 (11)
C8	1.0481 (7)	1.0437 (6)	−0.2087 (6)	0.0380 (13)
H8	1.0990	1.1181	−0.2742	0.046*
C9	1.1228 (7)	0.9109 (6)	−0.1952 (6)	0.0392 (13)
H9	1.2240	0.8936	−0.2535	0.047*
C10	1.0475 (6)	0.8002 (6)	−0.0934 (6)	0.0356 (12)
H10	1.1012	0.7096	−0.0841	0.043*
C11	0.8014 (8)	1.2041 (6)	−0.1279 (7)	0.0432 (14)
H11	0.8440	1.2830	−0.1935	0.052*
C12	0.6551 (7)	1.2204 (6)	−0.0396 (6)	0.0381 (13)
H12	0.5997	1.3098	−0.0436	0.046*
C13	0.5693 (6)	0.4601 (6)	0.2801 (6)	0.0336 (12)
C14	0.4522 (9)	0.3957 (7)	0.4171 (7)	0.0550 (19)
H14A	0.3507	0.4539	0.4228	0.066*
H14B	0.4825	0.3950	0.4891	0.066*
C15	0.9541 (6)	0.5230 (5)	0.2913 (5)	0.0293 (11)
C16	1.0576 (7)	0.3988 (6)	0.3569 (6)	0.0354 (12)
H16A	1.0700	0.4144	0.4303	0.043*
H16B	1.1602	0.3872	0.2894	0.043*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cu2	0.0264 (3)	0.0205 (3)	0.0253 (3)	−0.0018 (2)	−0.0022 (3)	−0.0080 (2)
I1	0.0913 (4)	0.0355 (3)	0.0650 (3)	−0.0196 (2)	−0.0323 (3)	0.0035 (2)
I2	0.0464 (3)	0.0329 (2)	0.0460 (3)	−0.01190 (17)	−0.00496 (18)	−0.01484 (18)
N1	0.028 (2)	0.025 (2)	0.022 (2)	−0.0010 (17)	−0.0070 (17)	−0.0096 (17)
N2	0.029 (2)	0.026 (2)	0.026 (2)	−0.0039 (18)	−0.0058 (18)	−0.0100 (18)
O1	0.036 (2)	0.032 (2)	0.0267 (19)	0.0013 (18)	−0.0049 (16)	−0.0137 (17)
O2	0.040 (2)	0.031 (2)	0.031 (2)	−0.0118 (17)	0.0021 (17)	−0.0139 (16)
O3	0.093 (4)	0.070 (3)	0.038 (3)	−0.050 (3)	0.012 (2)	−0.030 (2)
O4	0.034 (2)	0.0286 (19)	0.0270 (19)	0.0040 (16)	−0.0075 (16)	−0.0095 (16)
O5	0.049 (2)	0.034 (2)	0.044 (2)	−0.0013 (19)	−0.0081 (19)	−0.0224 (19)
C1	0.028 (3)	0.035 (3)	0.024 (3)	−0.003 (2)	−0.003 (2)	−0.012 (2)
C2	0.031 (3)	0.046 (3)	0.032 (3)	0.003 (3)	−0.007 (2)	−0.018 (3)
C3	0.036 (3)	0.037 (3)	0.043 (3)	0.009 (2)	−0.019 (3)	−0.019 (3)
C4	0.034 (3)	0.027 (3)	0.037 (3)	−0.001 (2)	−0.019 (2)	−0.013 (2)
C5	0.031 (3)	0.022 (2)	0.025 (2)	−0.002 (2)	−0.014 (2)	−0.009 (2)
C6	0.025 (3)	0.025 (3)	0.025 (2)	0.000 (2)	−0.010 (2)	−0.010 (2)
C7	0.035 (3)	0.029 (3)	0.030 (3)	−0.011 (2)	−0.013 (2)	−0.006 (2)
C8	0.040 (3)	0.042 (3)	0.032 (3)	−0.020 (3)	−0.010 (2)	−0.005 (2)
C9	0.031 (3)	0.049 (4)	0.032 (3)	−0.010 (3)	−0.001 (2)	−0.016 (3)
C10	0.032 (3)	0.038 (3)	0.031 (3)	−0.002 (2)	−0.002 (2)	−0.017 (2)
C11	0.055 (4)	0.024 (3)	0.051 (4)	−0.013 (3)	−0.025 (3)	−0.001 (3)
C12	0.042 (3)	0.025 (3)	0.050 (4)	−0.002 (2)	−0.022 (3)	−0.010 (3)
C13	0.033 (3)	0.030 (3)	0.031 (3)	−0.010 (2)	−0.001 (2)	−0.010 (2)
C14	0.071 (5)	0.048 (4)	0.039 (4)	−0.034 (4)	0.013 (3)	−0.022 (3)
C15	0.029 (3)	0.024 (3)	0.028 (3)	−0.007 (2)	−0.002 (2)	−0.007 (2)
C16	0.040 (3)	0.034 (3)	0.033 (3)	−0.003 (2)	−0.015 (3)	−0.010 (2)

Geometric parameters (Å, º) top

Cu2—O2	1.940 (4)	C3—C4	1.402 (8)
Cu2—O4	2.000 (4)	C3—H3	0.9300
Cu2—O5	2.775 (4)	C4—C5	1.402 (7)
Cu2—N2	2.013 (4)	C4—C12	1.433 (8)
Cu2—N1	2.024 (4)	C5—C6	1.416 (7)
Cu2—O1	2.261 (4)	C6—C7	1.404 (7)
I1—C16	2.134 (6)	C7—C8	1.403 (8)
I2—I2ⁱ	3.6772 (9)	C7—C11	1.434 (8)
I2—C14	2.117 (6)	C8—C9	1.352 (8)
N1—C1	1.322 (6)	C8—H8	0.9300
N1—C5	1.357 (6)	C9—C10	1.394 (8)
N2—C10	1.325 (7)	C9—H9	0.9300
N2—C6	1.349 (6)	C10—H10	0.9300
O1—H1C	0.8500	C11—C12	1.348 (9)
O1—H1B	0.8500	C11—H11	0.9300
O2—C13	1.262 (7)	C12—H12	0.9300
O3—C13	1.230 (7)	C13—C14	1.511 (8)
O4—C15	1.282 (6)	C14—H14A	0.9700
O5—C15	1.221 (6)	C14—H14B	0.9700
C1—C2	1.399 (8)	C15—C16	1.510 (7)
C1—H1A	0.9300	C16—H16A	0.9700
C2—C3	1.359 (9)	C16—H16B	0.9700
C2—H2	0.9300

Cg1···Cg3ⁱⁱ	3.505 (6)	Cg2···Cg4ⁱⁱⁱ	3.634 (6)
Cg1···Cg4ⁱⁱⁱ	3.584 (6)	I2···I2ⁱ	3.6772 (9)
Cg2···Cg3ⁱⁱ	3.625 (6)

O2—Cu2—O4	92.78 (16)	C7—C6—C5	120.1 (4)
O2—Cu2—N2	170.83 (17)	C8—C7—C6	116.6 (5)
O4—Cu2—N2	96.04 (17)	C8—C7—C11	125.3 (5)
O2—Cu2—N1	89.71 (17)	C6—C7—C11	118.1 (5)
O4—Cu2—N1	153.55 (16)	C9—C8—C7	119.8 (5)
N2—Cu2—N1	81.29 (17)	C9—C8—H8	120.1
O2—Cu2—O1	93.26 (15)	C7—C8—H8	120.1
O4—Cu2—O1	92.60 (14)	C8—C9—C10	119.7 (5)
N2—Cu2—O1	88.81 (16)	C8—C9—H9	120.2
N1—Cu2—O1	113.56 (15)	C10—C9—H9	120.2
C1—N1—C5	118.9 (4)	N2—C10—C9	122.7 (5)
C1—N1—Cu2	128.7 (4)	N2—C10—H10	118.7
C5—N1—Cu2	112.3 (3)	C9—C10—H10	118.7
C10—N2—C6	117.8 (5)	C12—C11—C7	122.0 (5)
C10—N2—Cu2	129.0 (4)	C12—C11—H11	119.0
C6—N2—Cu2	113.1 (3)	C7—C11—H11	119.0
Cu2—O1—H1C	109.3	C11—C12—C4	120.6 (5)
Cu2—O1—H1B	99.7	C11—C12—H12	119.7
H1C—O1—H1B	106.6	C4—C12—H12	119.7
C13—O2—Cu2	130.1 (3)	O3—C13—O2	126.2 (5)
C15—O4—Cu2	108.2 (3)	O3—C13—C14	122.0 (5)
N1—C1—C2	121.5 (5)	O2—C13—C14	111.7 (5)
N1—C1—H1A	119.2	C13—C14—I2	113.9 (4)
C2—C1—H1A	119.2	C13—C14—H14A	108.8
C3—C2—C1	120.4 (5)	I2—C14—H14A	108.8
C3—C2—H2	119.8	C13—C14—H14B	108.8
C1—C2—H2	119.8	I2—C14—H14B	108.8
C2—C3—C4	119.3 (5)	H14A—C14—H14B	107.7
C2—C3—H3	120.4	O5—C15—O4	125.0 (5)
C4—C3—H3	120.4	O5—C15—C16	118.5 (5)
C5—C4—C3	117.3 (5)	O4—C15—C16	116.5 (4)
C5—C4—C12	118.6 (5)	C15—C16—I1	109.7 (4)
C3—C4—C12	124.1 (5)	C15—C16—H16A	109.7
N1—C5—C4	122.6 (5)	I1—C16—H16A	109.7
N1—C5—C6	116.8 (4)	C15—C16—H16B	109.7
C4—C5—C6	120.6 (5)	I1—C16—H16B	109.7
N2—C6—C7	123.4 (5)	H16A—C16—H16B	108.2
N2—C6—C5	116.5 (4)

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1B···O3	0.85	1.84	2.639 (6)	156
O1—H1C···O4^iv	0.85	1.97	2.785 (5)	161
C3—H3···O1ⁱⁱⁱ	0.93	2.44	3.240 (7)	144
C11—H11···O5ⁱⁱ	0.93	2.71	3.508 (8)	144
C10—H10···O3^iv	0.93	2.68	3.431 (8)	138
C14—H14B···O2^v	0.97	2.59	3.436 (8)	146
C14—H14A···O5^v	0.97	2.64	3.219 (8)	119

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

Experimental details

Crystal data
Chemical formula	[Cu(C₂H₂IO₂)₂(C₁₂H₈N₂)(H₂O)]
M_r	631.63
Crystal system, space group	Triclinic, P1
Temperature (K)	273
a, b, c (Å)	9.5156 (11), 10.6293 (12), 11.3441 (13)
α, β, γ (°)	65.803 (2), 65.598 (2), 72.451 (2)
V (Å³)	940.94 (19)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	4.47
Crystal size (mm)	0.26 × 0.23 × 0.21

Data collection
Diffractometer	Bruker APEXII diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.389, 0.454
No. of measured, independent and observed [I > 2σ(I)] reflections	4948, 3305, 2934
R_int	0.016
(sin θ/λ)_max (Å⁻¹)	0.596

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.038, 0.104, 1.01
No. of reflections	3305
No. of parameters	237
No. of restraints	3
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	1.53, −1.68

Computer programs: SMART (Siemens, 1996), SAINT (Siemens, 1996), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Selected interatomic distances (Å) top

Cg1···Cg3ⁱ	3.505 (6)	Cg2···Cg4ⁱⁱ	3.634 (6)
Cg1···Cg4ⁱⁱ	3.584 (6)	I2···I2ⁱⁱⁱ	3.6772 (9)
Cg2···Cg3ⁱ	3.625 (6)

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1B···O3	0.85	1.84	2.639 (6)	156.4
O1—H1C···O4^iv	0.85	1.97	2.785 (5)	161.2
C3—H3···O1ⁱⁱ	0.93	2.44	3.240 (7)	143.6
C11—H11···O5ⁱ	0.93	2.71	3.508 (8)	144.0
C10—H10···O3^iv	0.93	2.68	3.431 (8)	138.4
C14—H14B···O2^v	0.97	2.59	3.436 (8)	145.5
C14—H14A···O5^v	0.97	2.64	3.219 (8)	118.8

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

Acknowledgements

The authors thank the Postgraduate Foundation of Taishan University (grant No. Y07-2-15) for financial support.

References

Liu, J.-W., Zhu, B., Tian, Y. & Gu, C.-S. (2006). Acta Cryst. E62, m2030–m2032. Web of Science CSD CrossRef CAS IUCr Journals Google Scholar
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Siemens (1996). SMART and SAINT. Siemens Analytical X-ray Instruments Inc., Madison, Wisconsin, USA. Google Scholar