Aqua­chlorido(4-methyl­benzoato-κO)(1,10-phenanthroline-κ2N,N′)copper(II)

Song, W.-D.; Wang, H.; Miao, Y.-L.

doi:10.1107/S1600536808010945

metal-organic compounds

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ISSN: 2056-9890

Volume 64| Part 5| May 2008| Page m716

doi:10.1107/S1600536808010945

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Aquachlorido(4-methylbenzoato-κO)(1,10-phenanthroline-κ²N,N′)copper(II)

Wen-Dong Song,^a ^* Hao Wang ^a and Yan-Li Miao ^a

^aCollege of Science, Guang Dong Ocean University, Zhanjiang 524088, People's Republic of China
^*Correspondence e-mail: songwd60@126.com

(Received 9 April 2008; accepted 19 April 2008; online 26 April 2008)

In the title mononuclear complex, [Cu(C₈H₇O₂)Cl(C₁₂H₈N₂)(H₂O)], the Cu^II atom is coordinated by one carboxylate O atom from a monodentate 4-methylbenzoate ligand, two N atoms from the 1,10-phenanthroline ligand, one chloride ion and one water molecule in a square-pyramidal geometry. The crystal structure exhibits inter- and intramolecular C—H⋯Cl, C—H⋯O, O—H⋯Cl and O—H⋯O hydrogen bonds, as well as C—H⋯π interactions of phenanthroline and methyl H atoms towards the π-systems of neighboring 4-methylbenzoate units and the pyridine rings of the phenanthroline system [centroid–centroid distances are 2.706 (2) and 2.992 (1) Å, respectively].

Related literature

For related literature, see: Song et al. (2007 ).

Experimental

Crystal data

[Cu(C₈H₇O₂)Cl(C₁₂H₈N₂)(H₂O)]
M_r = 432.35
Monoclinic, P 2₁ /n
a = 10.9095 (4) Å
b = 11.0546 (4) Å
c = 15.2059 (6) Å
β = 103.578 (2)°
V = 1782.58 (12) Å³
Z = 4
Mo Kα radiation
μ = 1.40 mm⁻¹
T = 296 (2) K
0.30 × 0.29 × 0.25 mm

Data collection

Bruker APEXII area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.679, T_max = 0.721
17233 measured reflections
4096 independent reflections
3470 reflections with I > 2σ(I)
R_int = 0.039

Refinement

R[F² > 2σ(F²)] = 0.031
wR(F²) = 0.087
S = 1.05
4096 reflections
251 parameters
3 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.36 e Å⁻³
Δρ_min = −0.41 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C10—H10⋯Cl1ⁱ	0.93	2.76	3.654 (2)	162
C1—H1⋯O1	0.93	2.52	2.988 (3)	112
O1W—H2W⋯Cl1ⁱ	0.816 (10)	2.259 (10)	3.0709 (17)	174 (3)
O1W—H1W⋯O2	0.812 (10)	1.788 (14)	2.526 (2)	150 (3)
C3—H3⋯Cg1ⁱⁱ	0.93	2.71	3.413 (2)	133
C20—H20B⋯Cg2ⁱⁱⁱ	0.93	2.99	3.627 (2)	125
Symmetry codes: (i) -x+1, -y+2, -z; (ii) $[-x+{\script{3\over 2}}, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (iii) x+1, y, z. Cg1 and Cg2 are the centroids of the C14–C19 and C1–C4,C12,N1 rings, respectively.

Data collection: APEX2 (Bruker, 2004 ); cell refinement: APEX2; data reduction: APEX2; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: DIAMOND (Brandenburg, 2001 ); software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808010945/zl2109sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808010945/zl2109Isup2.hkl

checkCIF report

Comment top

In the structural investigation of 4-methylbenzoate complexes, it has been found that the 4-methylbenzoic acid functions as a multidentate ligand [Song et al. (2007)], with versatile binding and coordination modes. In this paper, we report the crystal structure of the title compound, (I), a new Cu complex obtained by the reaction of 4-methylbenzoic acid, 1,10-phenanthroline and copper chloride in an alkaline aqueous solution.

As illustrated in Figure 1, the Cu^II atom exists in a square pyramidal environment, defined by one carboxyl O atom from a monodentate 4-methylbenzate ligand, two N atoms from the 1,10-phenanthroline ligand, one chlorine ion and a water molecule. The crystal structure exhibits inter and intramolecular C—H···Cl, C—H···O, O—H···Cl and O—H···O hydrogen bonding and C—H···π interactions of phenanthroline and methyl H atoms towards the π-systems of neighboring 4-methylbenzate units and of pyridine rings of the phenanthroline system. Centroid to centroid distances are 2.706 (2)Å and 2.992 (1) Å, respectively. (Table 1, Fig. 2, Cg1 = Ring (C14-C19) ; Cg2 = Ring (C1-C4 ,C12, N1)).

Related literature top

For related literature, see: Song et al. (2007). Cg1 and Cg2 are the centroids of the C14–C19 and C1–C4,C12,N1 rings, respectively.

Experimental top

A mixture of copper chloride (1 mmol), 4-methylbenzoic acid (1 mmol), phen (1 mmol), NaOH (1.5 mmol) and H₂O (12 ml) was placed in a 23 ml Teflon reactor, which was heated to 433 K for three days and then cooled to room temperature at a rate of 10 K h^-1. The crystals obtained were washed with water and dryed in air.

Computing details top

Data collection: APEX2 (Bruker, 2004); cell refinement: APEX2 (Bruker, 2004); data reduction: APEX2 (Bruker, 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: DIAMOND (Brandenburg, 2001); software used to prepare material for publication: SHELXTL (Sheldrick, 2008\bbr00).

Figures top

	Fig. 1. The structure of (I), showing the atomic numbering scheme. Non-H atoms are shown with 30% probability displacement ellipsoids.
	Fig. 2. A packing view of the title compound. The intermolecluar hydrogen bonds and C—H···π interactions are shown as dashed lines.

Aquachlorido(4-methylbenzoato-κO)(1,10-phenanthroline- κ²N,N')copper(II) top

Crystal data top

[Cu(C₈H₇O₂)Cl(C₁₂H₈N₂)(H₂O)]	F(000) = 884
M_r = 432.35	D_x = 1.611 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 2895 reflections
a = 10.9095 (4) Å	θ = 2.4–27.9°
b = 11.0546 (4) Å	µ = 1.40 mm⁻¹
c = 15.2059 (6) Å	T = 296 K
β = 103.578 (2)°	Block, blue
V = 1782.58 (12) Å³	0.30 × 0.29 × 0.25 mm
Z = 4

Data collection top

Bruker APEXII area-detector diffractometer	4096 independent reflections
Radiation source: fine-focus sealed tube	3470 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.039
ϕ and ω scans	θ_max = 27.5°, θ_min = 2.1°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −13→14
T_min = 0.679, T_max = 0.721	k = −14→14
17233 measured reflections	l = −19→19

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)] = 0.031	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.087	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	w = 1/[σ²(F_o²) + (0.0424P)² + 0.6484P] where P = (F_o² + 2F_c²)/3
4096 reflections	(Δ/σ)_max = 0.001
251 parameters	Δρ_max = 0.36 e Å⁻³
3 restraints	Δρ_min = −0.41 e Å⁻³

Crystal data top

[Cu(C₈H₇O₂)Cl(C₁₂H₈N₂)(H₂O)]	V = 1782.58 (12) Å³
M_r = 432.35	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 10.9095 (4) Å	µ = 1.40 mm⁻¹
b = 11.0546 (4) Å	T = 296 K
c = 15.2059 (6) Å	0.30 × 0.29 × 0.25 mm
β = 103.578 (2)°

Data collection top

Bruker APEXII area-detector diffractometer	4096 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	3470 reflections with I > 2σ(I)
T_min = 0.679, T_max = 0.721	R_int = 0.039
17233 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.031	3 restraints
wR(F²) = 0.087	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	Δρ_max = 0.36 e Å⁻³
4096 reflections	Δρ_min = −0.41 e Å⁻³
251 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
C1	0.64907 (19)	0.5567 (2)	0.17000 (14)	0.0353 (4)
H1	0.7299	0.5880	0.1905	0.042*
C2	0.6213 (2)	0.4448 (2)	0.20277 (15)	0.0417 (5)
H2	0.6826	0.4030	0.2445	0.050*
C3	0.5034 (2)	0.3969 (2)	0.17311 (14)	0.0401 (5)
H3	0.4843	0.3214	0.1934	0.048*
C4	0.41115 (19)	0.46272 (19)	0.11182 (13)	0.0323 (4)
C5	0.2842 (2)	0.4229 (2)	0.07897 (14)	0.0387 (5)
H5	0.2592	0.3489	0.0980	0.046*
C6	0.1996 (2)	0.4917 (2)	0.02029 (15)	0.0396 (5)
H6	0.1174	0.4638	−0.0003	0.047*
C7	0.23384 (19)	0.6059 (2)	−0.01065 (14)	0.0349 (4)
C8	0.1518 (2)	0.6819 (2)	−0.07119 (17)	0.0470 (6)
H8	0.0687	0.6587	−0.0949	0.056*
C9	0.1943 (2)	0.7895 (2)	−0.09500 (19)	0.0541 (7)
H9	0.1399	0.8406	−0.1345	0.065*
C10	0.3190 (2)	0.8236 (2)	−0.06052 (16)	0.0440 (5)
H10	0.3463	0.8979	−0.0775	0.053*
C11	0.35799 (17)	0.64676 (18)	0.02085 (12)	0.0287 (4)
C12	0.44711 (17)	0.57430 (17)	0.08258 (12)	0.0276 (4)
C13	0.85765 (19)	0.81625 (19)	0.06922 (14)	0.0343 (4)
C14	0.98797 (18)	0.77868 (18)	0.11736 (13)	0.0305 (4)
C15	1.09054 (19)	0.8525 (2)	0.11423 (15)	0.0375 (5)
H15	1.0786	0.9222	0.0790	0.045*
C16	1.20987 (19)	0.8220 (2)	0.16345 (15)	0.0397 (5)
H16	1.2773	0.8727	0.1614	0.048*
C17	1.23162 (19)	0.7185 (2)	0.21550 (14)	0.0354 (5)
C18	1.12943 (19)	0.6429 (2)	0.21623 (14)	0.0364 (5)
H18	1.1422	0.5713	0.2492	0.044*
C19	1.00983 (19)	0.67339 (19)	0.16855 (14)	0.0336 (4)
H19	0.9426	0.6226	0.1707	0.040*
C20	1.3607 (2)	0.6881 (3)	0.27276 (16)	0.0476 (6)
H20A	1.4229	0.7369	0.2541	0.071*
H20B	1.3784	0.6042	0.2654	0.071*
H20C	1.3629	0.7040	0.3352	0.071*
Cl1	0.55415 (5)	0.92640 (5)	0.16915 (4)	0.03802 (13)
Cu1	0.58608 (2)	0.78128 (2)	0.052071 (16)	0.02995 (9)
N1	0.56500 (14)	0.62052 (15)	0.11079 (10)	0.0290 (3)
N2	0.40076 (16)	0.75369 (16)	−0.00414 (12)	0.0327 (4)
O1	0.76822 (13)	0.76408 (14)	0.09531 (10)	0.0352 (3)
O2	0.84387 (16)	0.8934 (2)	0.00865 (14)	0.0697 (6)
O1W	0.60789 (15)	0.87990 (17)	−0.05137 (12)	0.0500 (4)
H1W	0.6788 (12)	0.908 (2)	−0.041 (2)	0.075*
H2W	0.563 (2)	0.9330 (19)	−0.0792 (19)	0.075*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0295 (10)	0.0428 (12)	0.0317 (10)	−0.0006 (9)	0.0034 (8)	0.0039 (9)
C2	0.0400 (12)	0.0482 (13)	0.0348 (11)	0.0060 (10)	0.0044 (9)	0.0126 (10)
C3	0.0479 (13)	0.0383 (12)	0.0354 (11)	−0.0028 (10)	0.0124 (9)	0.0073 (9)
C4	0.0370 (11)	0.0319 (10)	0.0296 (10)	−0.0045 (8)	0.0112 (8)	−0.0021 (8)
C5	0.0404 (12)	0.0388 (12)	0.0390 (11)	−0.0134 (9)	0.0132 (9)	−0.0029 (9)
C6	0.0306 (10)	0.0473 (13)	0.0404 (11)	−0.0141 (9)	0.0075 (9)	−0.0068 (10)
C7	0.0279 (10)	0.0428 (12)	0.0326 (10)	−0.0064 (8)	0.0042 (8)	−0.0054 (9)
C8	0.0257 (10)	0.0598 (15)	0.0492 (13)	−0.0063 (10)	−0.0041 (9)	0.0032 (12)
C9	0.0348 (12)	0.0607 (17)	0.0574 (16)	0.0031 (11)	−0.0078 (11)	0.0166 (13)
C10	0.0333 (11)	0.0433 (12)	0.0499 (13)	−0.0008 (10)	−0.0013 (10)	0.0133 (11)
C11	0.0263 (9)	0.0322 (10)	0.0271 (9)	−0.0029 (8)	0.0052 (7)	−0.0023 (8)
C12	0.0267 (9)	0.0329 (10)	0.0233 (8)	−0.0032 (8)	0.0059 (7)	−0.0025 (7)
C13	0.0283 (10)	0.0372 (11)	0.0355 (10)	−0.0047 (8)	0.0037 (8)	0.0011 (9)
C14	0.0263 (9)	0.0354 (11)	0.0295 (10)	−0.0033 (8)	0.0057 (8)	−0.0034 (8)
C15	0.0316 (10)	0.0395 (12)	0.0414 (11)	−0.0053 (9)	0.0083 (9)	0.0032 (9)
C16	0.0256 (10)	0.0486 (13)	0.0448 (12)	−0.0086 (9)	0.0080 (9)	−0.0058 (10)
C17	0.0260 (10)	0.0477 (13)	0.0317 (10)	0.0025 (9)	0.0054 (8)	−0.0089 (9)
C18	0.0342 (11)	0.0379 (11)	0.0362 (11)	0.0036 (9)	0.0067 (9)	0.0001 (9)
C19	0.0288 (10)	0.0360 (11)	0.0361 (10)	−0.0049 (8)	0.0081 (8)	−0.0038 (9)
C20	0.0290 (11)	0.0691 (16)	0.0419 (12)	0.0051 (11)	0.0026 (9)	−0.0065 (12)
Cl1	0.0337 (3)	0.0380 (3)	0.0397 (3)	0.0030 (2)	0.0033 (2)	0.0001 (2)
Cu1	0.02281 (13)	0.03156 (15)	0.03284 (15)	−0.00285 (9)	0.00123 (10)	0.00481 (10)
N1	0.0242 (8)	0.0334 (9)	0.0281 (8)	−0.0019 (7)	0.0035 (6)	0.0015 (7)
N2	0.0263 (8)	0.0349 (9)	0.0335 (9)	−0.0027 (7)	0.0002 (7)	0.0022 (7)
O1	0.0234 (7)	0.0412 (8)	0.0395 (8)	−0.0019 (6)	0.0048 (6)	0.0063 (6)
O2	0.0325 (9)	0.0915 (15)	0.0800 (13)	−0.0065 (9)	0.0027 (9)	0.0516 (12)
O1W	0.0322 (8)	0.0648 (11)	0.0498 (10)	0.0020 (8)	0.0033 (7)	0.0280 (9)

Geometric parameters (Å, º) top

C1—N1	1.327 (2)	C13—O2	1.238 (3)
C1—C2	1.394 (3)	C13—O1	1.274 (2)
C1—H1	0.9300	C13—C14	1.497 (3)
C2—C3	1.366 (3)	C14—C19	1.389 (3)
C2—H2	0.9300	C14—C15	1.395 (3)
C3—C4	1.403 (3)	C15—C16	1.382 (3)
C3—H3	0.9300	C15—H15	0.9300
C4—C12	1.398 (3)	C16—C17	1.381 (3)
C4—C5	1.427 (3)	C16—H16	0.9300
C5—C6	1.356 (3)	C17—C18	1.395 (3)
C5—H5	0.9300	C17—C20	1.509 (3)
C6—C7	1.428 (3)	C18—C19	1.377 (3)
C6—H6	0.9300	C18—H18	0.9300
C7—C11	1.401 (3)	C19—H19	0.9300
C7—C8	1.403 (3)	C20—H20A	0.9600
C8—C9	1.356 (3)	C20—H20B	0.9600
C8—H8	0.9300	C20—H20C	0.9600
C9—C10	1.390 (3)	Cl1—Cu1	2.4810 (6)
C9—H9	0.9300	Cu1—O1	1.9503 (14)
C10—N2	1.330 (3)	Cu1—O1W	1.9736 (16)
C10—H10	0.9300	Cu1—N2	2.0248 (17)
C11—N2	1.357 (3)	Cu1—N1	2.0261 (17)
C11—C12	1.428 (3)	O1W—H1W	0.812 (10)
C12—N1	1.357 (2)	O1W—H2W	0.816 (10)

N1—C1—C2	122.73 (19)	C16—C15—C14	120.0 (2)
N1—C1—H1	118.6	C16—C15—H15	120.0
C2—C1—H1	118.6	C14—C15—H15	120.0
C3—C2—C1	119.5 (2)	C17—C16—C15	121.7 (2)
C3—C2—H2	120.2	C17—C16—H16	119.1
C1—C2—H2	120.2	C15—C16—H16	119.1
C2—C3—C4	119.4 (2)	C16—C17—C18	118.09 (19)
C2—C3—H3	120.3	C16—C17—C20	121.8 (2)
C4—C3—H3	120.3	C18—C17—C20	120.1 (2)
C12—C4—C3	117.22 (18)	C19—C18—C17	120.6 (2)
C12—C4—C5	118.85 (19)	C19—C18—H18	119.7
C3—C4—C5	123.92 (19)	C17—C18—H18	119.7
C6—C5—C4	120.8 (2)	C18—C19—C14	121.09 (19)
C6—C5—H5	119.6	C18—C19—H19	119.5
C4—C5—H5	119.6	C14—C19—H19	119.5
C5—C6—C7	121.51 (19)	C17—C20—H20A	109.5
C5—C6—H6	119.2	C17—C20—H20B	109.5
C7—C6—H6	119.2	H20A—C20—H20B	109.5
C11—C7—C8	116.6 (2)	C17—C20—H20C	109.5
C11—C7—C6	118.62 (19)	H20A—C20—H20C	109.5
C8—C7—C6	124.78 (19)	H20B—C20—H20C	109.5
C9—C8—C7	119.7 (2)	O1—Cu1—O1W	91.07 (6)
C9—C8—H8	120.2	O1—Cu1—N2	164.79 (7)
C7—C8—H8	120.2	O1W—Cu1—N2	92.41 (7)
C8—C9—C10	120.2 (2)	O1—Cu1—N1	88.73 (6)
C8—C9—H9	119.9	O1W—Cu1—N1	152.03 (8)
C10—C9—H9	119.9	N2—Cu1—N1	81.29 (7)
N2—C10—C9	122.3 (2)	O1—Cu1—Cl1	97.16 (5)
N2—C10—H10	118.9	O1W—Cu1—Cl1	106.16 (6)
C9—C10—H10	118.9	N2—Cu1—Cl1	96.07 (5)
N2—C11—C7	123.57 (18)	N1—Cu1—Cl1	101.62 (5)
N2—C11—C12	116.53 (16)	C1—N1—C12	117.86 (17)
C7—C11—C12	119.89 (18)	C1—N1—Cu1	129.28 (14)
N1—C12—C4	123.21 (18)	C12—N1—Cu1	112.85 (12)
N1—C12—C11	116.44 (17)	C10—N2—C11	117.66 (18)
C4—C12—C11	120.35 (17)	C10—N2—Cu1	129.52 (15)
O2—C13—O1	125.12 (19)	C11—N2—Cu1	112.82 (13)
O2—C13—C14	119.36 (18)	C13—O1—Cu1	130.15 (14)
O1—C13—C14	115.52 (18)	Cu1—O1W—H1W	110 (2)
C19—C14—C15	118.41 (19)	Cu1—O1W—H2W	130 (2)
C19—C14—C13	121.65 (18)	H1W—O1W—H2W	105.0 (15)
C15—C14—C13	119.90 (19)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C10—H10···Cl1ⁱ	0.93	2.76	3.654 (2)	162
C1—H1···O1	0.93	2.52	2.988 (3)	112
O1W—H2W···Cl1ⁱ	0.82 (1)	2.26 (1)	3.0709 (17)	174 (3)
O1W—H1W···O2	0.81 (1)	1.79 (1)	2.526 (2)	150 (3)
C3—H3···Cg1ⁱⁱ	0.93	2.71	3.413 (2)	133
C20—H20B···Cg2ⁱⁱⁱ	0.93	2.99	3.627 (2)	125

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

Experimental details

Crystal data
Chemical formula	[Cu(C₈H₇O₂)Cl(C₁₂H₈N₂)(H₂O)]
M_r	432.35
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	296
a, b, c (Å)	10.9095 (4), 11.0546 (4), 15.2059 (6)
β (°)	103.578 (2)
V (Å³)	1782.58 (12)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	1.40
Crystal size (mm)	0.30 × 0.29 × 0.25

Data collection
Diffractometer	Bruker APEXII area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.679, 0.721
No. of measured, independent and observed [I > 2σ(I)] reflections	17233, 4096, 3470
R_int	0.039
(sin θ/λ)_max (Å⁻¹)	0.650

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.031, 0.087, 1.05
No. of reflections	4096
No. of parameters	251
No. of restraints	3
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.36, −0.41

Computer programs: APEX2 (Bruker, 2004), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), DIAMOND (Brandenburg, 2001), SHELXTL (Sheldrick, 2008\bbr00).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C10—H10···Cl1ⁱ	0.93	2.76	3.654 (2)	162.0
C1—H1···O1	0.93	2.52	2.988 (3)	111.6
O1W—H2W···Cl1ⁱ	0.816 (10)	2.259 (10)	3.0709 (17)	174 (3)
O1W—H1W···O2	0.812 (10)	1.788 (14)	2.526 (2)	150 (3)
C3—H3···Cg1ⁱⁱ	0.93	2.71	3.413 (2)	133
C20—H20B···Cg2ⁱⁱⁱ	0.93	2.99	3.627 (2)	125

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

Acknowledgements

The authors acknowledge Guang Dong Ocean University for supporting this work.

References

Brandenburg, K. (2001). DIAMOND. Crystal Impact GbR, Bonn, Germany. Google Scholar
Bruker (2004). APEX2 and SMART. Bruker AXS Inc, Madison, Wisconsin, USA. 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
Song, W.-D., Gu, C.-S., Hao, X.-M. & Liu, J.-W. (2007). Acta Cryst. E63, m1023–m1024. Web of Science CSD CrossRef CAS IUCr Journals Google Scholar