[N′-(4-Meth­oxy-2-oxidobenzyl­idene)4-nitro­benzohydrazidato-κ3O,N,O′](pyridine-κN)copper(II)

Mohd Lair, N.; Mohd Ali, H.; Ng, S.W.

doi:10.1107/S1600536808042803

metal-organic compounds

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ISSN: 2056-9890

Volume 65| Part 1| January 2009| Page m121

doi:10.1107/S1600536808042803

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[N′-(4-Methoxy-2-oxidobenzylidene)4-nitrobenzohydrazidato-κ³O,N,O′](pyridine-κN)copper(II)

Nooraziah Mohd Lair,^a Hapipah Mohd Ali ^a and Seik Weng Ng ^a ^*

^aDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
^*Correspondence e-mail: seikweng@um.edu.my

(Received 15 December 2008; accepted 16 December 2008; online 20 December 2008)

The pyridine-coordinated Cu^II atom in the title Schiff base complex, [Cu(C₁₅H₁₁N₃O₅)(C₅H₅N)], is O,N,O′-chelated by the doubly deprotonated Schiff base ligand. The metal centre is in a square-planar coordination geometry.

Related literature

For the pyridine adducts of copper derivatives of similar ligands, see: Ali et al. (2004 ); Chen & Liu (2004 ); Das & Pal (2005 ); Fariati et al. (2002 ); Lu & Liu (2005 ); Lu et al. (2003 ).

Experimental

Crystal data

[Cu(C₁₅H₁₁N₃O₅)(C₅H₅N)]
M_r = 455.91
Triclinic, $[P \overline 1]$
a = 6.3529 (1) Å
b = 9.8409 (2) Å
c = 15.1303 (3) Å
α = 98.063 (1)°
β = 92.011 (1)°
γ = 107.088 (1)°
V = 892.31 (3) Å³
Z = 2
Mo Kα radiation
μ = 1.27 mm⁻¹
T = 100 (2) K
0.40 × 0.10 × 0.05 mm

Data collection

Bruker SMART APEX diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.807, T_max = 1.000 (expected range = 0.757–0.939)
6268 measured reflections
3942 independent reflections
3605 reflections with I > 2σ(I)
R_int = 0.013

Refinement

R[F² > 2σ(F²)] = 0.028
wR(F²) = 0.087
S = 1.09
3942 reflections
272 parameters
H-atom parameters constrained
Δρ_max = 0.45 e Å⁻³
Δρ_min = −0.32 e Å⁻³

Data collection: APEX2 (Bruker, 2007 ); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: X-SEED (Barbour, 2001 ); software used to prepare material for publication: publCIF (Westrip, 2009 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808042803/bt2838sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808042803/bt2838Isup2.hkl

checkCIF report

Related literature top

For the pyridine adducts of copper derivatives of similar ligands, see: Ali et al. (2004); Chen & Liu (2004); Das & Pal (2005); Fariati et al. (2002); Lu & Liu (2005); Lu et al. (2003).

Experimental top

N'-2-Hydroxy-3-methoxybenzylidene)-nitrobenzohydrazide (0.30 g, 1 mmol) and copper acetate (0.20 g, 1 mmol) were heated in a ethanol (50 ml) for 2 hours. The solvent was removed and the resulting compound recrystallized from pyridine.

Computing details top

Data collection: APEX2 (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: X-SEED (Barbour, 2001); software used to prepare material for publication: pubCIF (Westrip, 2009).

Figures top

Fig. 1. Displacement ellipsoid plot (Barbour, 2001) of Cu(C₅H₅N)(C₁₅H₁₁N₃O₅) at the 70% probability level. Hydrogen atoms are drawn as spheres of arbitrary radius.

[N'-(4-Methoxy-2-oxidobenzylidene)-4-nitrobenzohydrazidato- κ³O,N,O'](pyridine-κN)copper(II) top

Crystal data top

[Cu(C₁₅H₁₁N₃O₅)(C₅H₅N)]	Z = 2
M_r = 455.91	F(000) = 466
Triclinic, P1	D_x = 1.697 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 6.3529 (1) Å	Cell parameters from 3716 reflections
b = 9.8409 (2) Å	θ = 2.4–29.2°
c = 15.1303 (3) Å	µ = 1.27 mm⁻¹
α = 98.063 (1)°	T = 100 K
β = 92.011 (1)°	Block, brown
γ = 107.088 (1)°	0.40 × 0.10 × 0.05 mm
V = 892.31 (3) Å³

Data collection top

Bruker SMART APEX diffractometer	3942 independent reflections
Radiation source: fine-focus sealed tube	3605 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.013
ω scans	θ_max = 27.5°, θ_min = 1.4°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −6→8
T_min = 0.807, T_max = 1.000	k = −12→12
6268 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)] = 0.028	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.087	H-atom parameters constrained
S = 1.09	w = 1/[σ²(F_o²) + (0.0494P)² + 0.535P] where P = (F_o² + 2F_c²)/3
3942 reflections	(Δ/σ)_max = 0.001
272 parameters	Δρ_max = 0.45 e Å⁻³
0 restraints	Δρ_min = −0.32 e Å⁻³

Crystal data top

[Cu(C₁₅H₁₁N₃O₅)(C₅H₅N)]	γ = 107.088 (1)°
M_r = 455.91	V = 892.31 (3) Å³
Triclinic, P1	Z = 2
a = 6.3529 (1) Å	Mo Kα radiation
b = 9.8409 (2) Å	µ = 1.27 mm⁻¹
c = 15.1303 (3) Å	T = 100 K
α = 98.063 (1)°	0.40 × 0.10 × 0.05 mm
β = 92.011 (1)°

Data collection top

Bruker SMART APEX diffractometer	3942 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	3605 reflections with I > 2σ(I)
T_min = 0.807, T_max = 1.000	R_int = 0.013
6268 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.028	0 restraints
wR(F²) = 0.087	H-atom parameters constrained
S = 1.09	Δρ_max = 0.45 e Å⁻³
3942 reflections	Δρ_min = −0.32 e Å⁻³
272 parameters

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
Cu1	1.14506 (4)	0.70062 (2)	0.728016 (14)	0.01312 (9)
N1	0.9381 (3)	0.64556 (17)	0.62386 (11)	0.0150 (3)
N2	1.0273 (3)	0.68298 (18)	0.54424 (10)	0.0159 (3)
N3	1.7555 (3)	0.93172 (18)	0.27544 (11)	0.0189 (4)
N4	1.3792 (3)	0.78081 (17)	0.82931 (11)	0.0145 (3)
O1	0.9305 (2)	0.61658 (15)	0.80405 (9)	0.0163 (3)
O2	0.2533 (2)	0.39329 (16)	0.90700 (9)	0.0199 (3)
O3	1.3444 (2)	0.77637 (15)	0.64095 (9)	0.0159 (3)
O4	1.6632 (3)	0.91481 (17)	0.20033 (9)	0.0247 (3)
O5	1.9560 (3)	0.9856 (2)	0.29243 (11)	0.0311 (4)
C1	0.7183 (3)	0.5521 (2)	0.78294 (13)	0.0139 (4)
C2	0.5869 (3)	0.5009 (2)	0.85092 (13)	0.0152 (4)
H2	0.6540	0.5120	0.9097	0.018*
C3	0.3615 (3)	0.4346 (2)	0.83442 (13)	0.0149 (4)
C4	0.2562 (3)	0.4147 (2)	0.74829 (13)	0.0151 (4)
H4	0.1016	0.3693	0.7371	0.018*
C5	0.3837 (3)	0.4630 (2)	0.68048 (13)	0.0146 (4)
H5	0.3142	0.4495	0.6219	0.018*
C6	0.6124 (3)	0.5313 (2)	0.69468 (12)	0.0140 (4)
C7	0.7290 (3)	0.5785 (2)	0.61964 (12)	0.0149 (4)
H7	0.6471	0.5592	0.5631	0.018*
C8	0.0219 (3)	0.3204 (3)	0.89270 (15)	0.0247 (5)
H8A	−0.0352	0.2939	0.9492	0.037*
H8B	−0.0038	0.2333	0.8484	0.037*
H8C	−0.0540	0.3840	0.8707	0.037*
C9	1.2393 (3)	0.7493 (2)	0.56222 (12)	0.0140 (4)
C10	1.3714 (3)	0.79538 (19)	0.48671 (12)	0.0142 (4)
C11	1.2684 (3)	0.7902 (2)	0.40223 (13)	0.0162 (4)
H11	1.1119	0.7555	0.3927	0.019*
C12	1.3932 (3)	0.8352 (2)	0.33284 (13)	0.0174 (4)
H12	1.3242	0.8321	0.2755	0.021*
C13	1.6204 (3)	0.8849 (2)	0.34864 (12)	0.0149 (4)
C14	1.7277 (3)	0.8905 (2)	0.43096 (13)	0.0162 (4)
H14	1.8844	0.9243	0.4396	0.019*
C15	1.6016 (3)	0.8457 (2)	0.50049 (12)	0.0146 (4)
H15	1.6720	0.8492	0.5576	0.017*
C16	1.3332 (3)	0.7615 (2)	0.91374 (13)	0.0189 (4)
H16	1.1851	0.7146	0.9246	0.023*
C17	1.4910 (3)	0.8068 (2)	0.98487 (13)	0.0219 (4)
H17	1.4524	0.7913	1.0435	0.026*
C18	1.7074 (3)	0.8753 (2)	0.96950 (14)	0.0210 (4)
H18	1.8197	0.9079	1.0175	0.025*
C19	1.7569 (3)	0.8955 (2)	0.88305 (13)	0.0189 (4)
H19	1.9041	0.9416	0.8707	0.023*
C20	1.5893 (3)	0.8476 (2)	0.81504 (13)	0.0161 (4)
H20	1.6239	0.8625	0.7559	0.019*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cu1	0.01168 (13)	0.01707 (13)	0.00996 (13)	0.00263 (9)	0.00095 (8)	0.00366 (8)
N1	0.0165 (8)	0.0172 (8)	0.0117 (7)	0.0044 (6)	0.0032 (6)	0.0046 (6)
N2	0.0166 (8)	0.0193 (8)	0.0109 (7)	0.0027 (7)	0.0034 (6)	0.0048 (6)
N3	0.0245 (9)	0.0184 (8)	0.0147 (8)	0.0060 (7)	0.0075 (7)	0.0047 (6)
N4	0.0133 (8)	0.0162 (8)	0.0137 (8)	0.0039 (6)	0.0007 (6)	0.0032 (6)
O1	0.0109 (6)	0.0234 (7)	0.0136 (6)	0.0025 (5)	0.0012 (5)	0.0057 (5)
O2	0.0136 (7)	0.0297 (8)	0.0154 (7)	0.0027 (6)	0.0032 (5)	0.0082 (6)
O3	0.0139 (7)	0.0218 (7)	0.0110 (6)	0.0028 (5)	0.0006 (5)	0.0046 (5)
O4	0.0325 (9)	0.0307 (8)	0.0127 (7)	0.0103 (7)	0.0053 (6)	0.0074 (6)
O5	0.0224 (8)	0.0431 (10)	0.0229 (8)	−0.0003 (7)	0.0092 (7)	0.0092 (7)
C1	0.0131 (9)	0.0140 (8)	0.0154 (9)	0.0050 (7)	0.0014 (7)	0.0030 (7)
C2	0.0143 (9)	0.0192 (9)	0.0130 (9)	0.0056 (8)	0.0009 (7)	0.0041 (7)
C3	0.0156 (9)	0.0160 (9)	0.0141 (9)	0.0048 (7)	0.0042 (7)	0.0046 (7)
C4	0.0125 (9)	0.0156 (9)	0.0157 (9)	0.0025 (7)	0.0007 (7)	0.0018 (7)
C5	0.0167 (9)	0.0141 (8)	0.0124 (8)	0.0041 (7)	−0.0001 (7)	0.0011 (7)
C6	0.0156 (9)	0.0133 (8)	0.0127 (8)	0.0040 (7)	0.0021 (7)	0.0021 (7)
C7	0.0164 (9)	0.0153 (9)	0.0115 (8)	0.0027 (7)	−0.0009 (7)	0.0024 (7)
C8	0.0126 (10)	0.0395 (13)	0.0216 (10)	0.0032 (9)	0.0058 (8)	0.0122 (9)
C9	0.0169 (9)	0.0146 (9)	0.0116 (8)	0.0055 (7)	0.0025 (7)	0.0038 (7)
C10	0.0171 (9)	0.0129 (8)	0.0130 (9)	0.0046 (7)	0.0022 (7)	0.0034 (7)
C11	0.0146 (9)	0.0202 (9)	0.0135 (9)	0.0045 (7)	0.0005 (7)	0.0033 (7)
C12	0.0211 (10)	0.0199 (9)	0.0111 (9)	0.0057 (8)	0.0007 (7)	0.0033 (7)
C13	0.0197 (10)	0.0138 (9)	0.0116 (8)	0.0048 (7)	0.0055 (7)	0.0035 (7)
C14	0.0154 (9)	0.0159 (9)	0.0166 (9)	0.0035 (7)	0.0019 (7)	0.0021 (7)
C15	0.0168 (9)	0.0163 (9)	0.0111 (8)	0.0050 (7)	0.0014 (7)	0.0037 (7)
C16	0.0148 (10)	0.0249 (10)	0.0147 (9)	0.0021 (8)	0.0019 (7)	0.0031 (8)
C17	0.0193 (10)	0.0293 (11)	0.0125 (9)	0.0008 (9)	0.0010 (8)	0.0029 (8)
C18	0.0186 (10)	0.0248 (10)	0.0149 (9)	0.0007 (8)	−0.0034 (8)	0.0013 (8)
C19	0.0143 (9)	0.0197 (10)	0.0199 (10)	0.0008 (8)	0.0009 (8)	0.0033 (8)
C20	0.0156 (9)	0.0176 (9)	0.0143 (9)	0.0033 (7)	0.0026 (7)	0.0036 (7)

Geometric parameters (Å, º) top

Cu1—O1	1.8922 (14)	C6—C7	1.435 (3)
Cu1—N1	1.9239 (16)	C7—H7	0.9500
Cu1—O3	1.9320 (14)	C8—H8A	0.9800
Cu1—N4	1.9989 (16)	C8—H8B	0.9800
N1—C7	1.293 (3)	C8—H8C	0.9800
N1—N2	1.399 (2)	C9—C10	1.485 (3)
N2—C9	1.312 (3)	C10—C15	1.397 (3)
N3—O5	1.229 (2)	C10—C11	1.403 (3)
N3—O4	1.227 (2)	C11—C12	1.382 (3)
N3—C13	1.467 (2)	C11—H11	0.9500
N4—C20	1.343 (3)	C12—C13	1.381 (3)
N4—C16	1.347 (2)	C12—H12	0.9500
O1—C1	1.316 (2)	C13—C14	1.385 (3)
O2—C3	1.363 (2)	C14—C15	1.387 (3)
O2—C8	1.427 (2)	C14—H14	0.9500
O3—C9	1.299 (2)	C15—H15	0.9500
C1—C2	1.403 (3)	C16—C17	1.375 (3)
C1—C6	1.434 (3)	C16—H16	0.9500
C2—C3	1.385 (3)	C17—C18	1.386 (3)
C2—H2	0.9500	C17—H17	0.9500
C3—C4	1.405 (3)	C18—C19	1.384 (3)
C4—C5	1.380 (3)	C18—H18	0.9500
C4—H4	0.9500	C19—C20	1.381 (3)
C5—C6	1.404 (3)	C19—H19	0.9500
C5—H5	0.9500	C20—H20	0.9500

O1—Cu1—N1	93.57 (6)	O2—C8—H8B	109.5
O1—Cu1—O3	174.58 (6)	H8A—C8—H8B	109.5
N1—Cu1—O3	81.17 (6)	O2—C8—H8C	109.5
O1—Cu1—N4	92.67 (6)	H8A—C8—H8C	109.5
N1—Cu1—N4	172.51 (7)	H8B—C8—H8C	109.5
O3—Cu1—N4	92.68 (6)	O3—C9—N2	125.19 (17)
C7—N1—N2	117.25 (16)	O3—C9—C10	117.01 (17)
C7—N1—Cu1	127.41 (13)	N2—C9—C10	117.79 (16)
N2—N1—Cu1	115.34 (12)	C15—C10—C11	119.71 (17)
C9—N2—N1	108.05 (15)	C15—C10—C9	119.31 (16)
O5—N3—O4	123.25 (17)	C11—C10—C9	120.98 (18)
O5—N3—C13	118.27 (16)	C12—C11—C10	120.41 (18)
O4—N3—C13	118.47 (17)	C12—C11—H11	119.8
C20—N4—C16	117.86 (17)	C10—C11—H11	119.8
C20—N4—Cu1	121.38 (13)	C11—C12—C13	118.53 (17)
C16—N4—Cu1	120.64 (14)	C11—C12—H12	120.7
C1—O1—Cu1	127.54 (12)	C13—C12—H12	120.7
C3—O2—C8	117.33 (15)	C12—C13—C14	122.62 (18)
C9—O3—Cu1	110.23 (12)	C12—C13—N3	119.26 (17)
O1—C1—C2	118.11 (17)	C14—C13—N3	118.12 (18)
O1—C1—C6	124.11 (17)	C15—C14—C13	118.62 (18)
C2—C1—C6	117.78 (17)	C15—C14—H14	120.7
C3—C2—C1	121.55 (17)	C13—C14—H14	120.7
C3—C2—H2	119.2	C14—C15—C10	120.11 (17)
C1—C2—H2	119.2	C14—C15—H15	119.9
O2—C3—C2	115.33 (17)	C10—C15—H15	119.9
O2—C3—C4	123.65 (18)	N4—C16—C17	122.91 (19)
C2—C3—C4	121.01 (18)	N4—C16—H16	118.5
C5—C4—C3	118.12 (18)	C17—C16—H16	118.5
C5—C4—H4	120.9	C16—C17—C18	118.84 (19)
C3—C4—H4	120.9	C16—C17—H17	120.6
C4—C5—C6	122.53 (17)	C18—C17—H17	120.6
C4—C5—H5	118.7	C19—C18—C17	118.81 (19)
C6—C5—H5	118.7	C19—C18—H18	120.6
C5—C6—C1	119.00 (17)	C17—C18—H18	120.6
C5—C6—C7	117.98 (17)	C20—C19—C18	119.05 (19)
C1—C6—C7	123.02 (17)	C20—C19—H19	120.5
N1—C7—C6	124.30 (17)	C18—C19—H19	120.5
N1—C7—H7	117.9	N4—C20—C19	122.52 (18)
C6—C7—H7	117.9	N4—C20—H20	118.7
O2—C8—H8A	109.5	C19—C20—H20	118.7

O1—Cu1—N1—C7	1.77 (18)	C5—C6—C7—N1	178.35 (18)
O3—Cu1—N1—C7	−179.56 (18)	C1—C6—C7—N1	−1.0 (3)
O1—Cu1—N1—N2	−178.07 (13)	Cu1—O3—C9—N2	1.5 (2)
O3—Cu1—N1—N2	0.60 (12)	Cu1—O3—C9—C10	−177.59 (12)
C7—N1—N2—C9	−179.91 (17)	N1—N2—C9—O3	−1.0 (3)
Cu1—N1—N2—C9	−0.05 (19)	N1—N2—C9—C10	178.08 (15)
O1—Cu1—N4—C20	174.53 (15)	O3—C9—C10—C15	9.0 (3)
O3—Cu1—N4—C20	−4.54 (15)	N2—C9—C10—C15	−170.09 (17)
O1—Cu1—N4—C16	−1.39 (16)	O3—C9—C10—C11	−170.48 (17)
O3—Cu1—N4—C16	179.54 (15)	N2—C9—C10—C11	10.4 (3)
N1—Cu1—O1—C1	−2.34 (16)	C15—C10—C11—C12	−0.4 (3)
N4—Cu1—O1—C1	173.51 (16)	C9—C10—C11—C12	179.15 (17)
N1—Cu1—O3—C9	−1.01 (12)	C10—C11—C12—C13	0.1 (3)
N4—Cu1—O3—C9	−176.72 (13)	C11—C12—C13—C14	0.4 (3)
Cu1—O1—C1—C2	−178.09 (13)	C11—C12—C13—N3	179.37 (17)
Cu1—O1—C1—C6	1.7 (3)	O5—N3—C13—C12	174.64 (18)
O1—C1—C2—C3	178.63 (17)	O4—N3—C13—C12	−5.6 (3)
C6—C1—C2—C3	−1.1 (3)	O5—N3—C13—C14	−6.3 (3)
C8—O2—C3—C2	−178.07 (18)	O4—N3—C13—C14	173.44 (18)
C8—O2—C3—C4	2.8 (3)	C12—C13—C14—C15	−0.6 (3)
C1—C2—C3—O2	−178.47 (17)	N3—C13—C14—C15	−179.62 (16)
C1—C2—C3—C4	0.7 (3)	C13—C14—C15—C10	0.4 (3)
O2—C3—C4—C5	179.17 (17)	C11—C10—C15—C14	0.1 (3)
C2—C3—C4—C5	0.0 (3)	C9—C10—C15—C14	−179.40 (17)
C3—C4—C5—C6	−0.4 (3)	C20—N4—C16—C17	−0.1 (3)
C4—C5—C6—C1	−0.1 (3)	Cu1—N4—C16—C17	175.93 (16)
C4—C5—C6—C7	−179.44 (17)	N4—C16—C17—C18	0.0 (3)
O1—C1—C6—C5	−178.95 (17)	C16—C17—C18—C19	−0.1 (3)
C2—C1—C6—C5	0.8 (3)	C17—C18—C19—C20	0.4 (3)
O1—C1—C6—C7	0.4 (3)	C16—N4—C20—C19	0.4 (3)
C2—C1—C6—C7	−179.86 (17)	Cu1—N4—C20—C19	−175.60 (15)
N2—N1—C7—C6	179.34 (16)	C18—C19—C20—N4	−0.6 (3)
Cu1—N1—C7—C6	−0.5 (3)

Experimental details

Crystal data
Chemical formula	[Cu(C₁₅H₁₁N₃O₅)(C₅H₅N)]
M_r	455.91
Crystal system, space group	Triclinic, P1
Temperature (K)	100
a, b, c (Å)	6.3529 (1), 9.8409 (2), 15.1303 (3)
α, β, γ (°)	98.063 (1), 92.011 (1), 107.088 (1)
V (Å³)	892.31 (3)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	1.27
Crystal size (mm)	0.40 × 0.10 × 0.05

Data collection
Diffractometer	Bruker SMART APEX diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.807, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections	6268, 3942, 3605
R_int	0.013
(sin θ/λ)_max (Å⁻¹)	0.650

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.028, 0.087, 1.09
No. of reflections	3942
No. of parameters	272
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.45, −0.32

Computer programs: APEX2 (Bruker, 2007), SAINT (Bruker, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), X-SEED (Barbour, 2001), pubCIF (Westrip, 2009).

Acknowledgements

We thank the University of Malaya for funding this study (Science Fund grants 12–02-03–2031, 12–02-03–2051).

References

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