1-Allyl-3-chloro-6-nitro-1H-indazole

El Brahmi, N.; Mohamed, B.; Essassi, E.M.; Zouihri, H.; Ng, S.W.

doi:10.1107/S1600536809034138

organic compounds

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ISSN: 2056-9890

Volume 65| Part 10| October 2009| Page o2320

doi:10.1107/S1600536809034138

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1-Allyl-3-chloro-6-nitro-1H-indazole

Nabil El Brahmi,^a Benchidmi Mohamed,^a El Mokhtar Essassi,^a Hafid Zouihri ^b and Seik Weng Ng ^c ^*

^aLaboratoire de Chimie Organique Hétérocyclique, Pôle de Compétences Pharmacochimie, Université Mohammed V-Agdal, BP 1014 Avenue Ibn Batout, Rabat, Morocco, ^bCNRST Division UATRS, Angle Allal Fassi/FAR, BP 8027 Hay Riad, 10000 Rabat, Morocco, and ^cDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
^*Correspondence e-mail: seikweng@um.edu.my

(Received 25 August 2009; accepted 26 August 2009; online 5 September 2009)

The indazole system in each of the two independent molecules of the title compound, C₁₀H₈ClN₃O₂, is planar (r.m.s. deviations = 0.005 and 0.005 Å). The nitro group is coplanar with the fused-ring system [dihedral angles = 1.3 (3) and 4.8 (3) Å].

Related literature

For a review of indazoles, see: Elguéro (1996 ); Elguéro et al. (1995 ).

Experimental

Crystal data

C₁₀H₈ClN₃O₂
M_r = 237.64
Monoclinic, P 2₁ /n
a = 7.6804 (1) Å
b = 9.9559 (2) Å
c = 28.4344 (4) Å
β = 95.144 (1)°
V = 2165.49 (6) Å³
Z = 8
Mo Kα radiation
μ = 0.34 mm⁻¹
T = 295 K
0.4 × 0.3 × 0.2 mm

Data collection

Bruker APEXII diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.884, T_max = 0.934
19833 measured reflections
3777 independent reflections
2665 reflections with I > 2σ(I)
R_int = 0.032

Refinement

R[F² > 2σ(F²)] = 0.056
wR(F²) = 0.185
S = 1.07
3777 reflections
289 parameters
H-atom parameters constrained
Δρ_max = 0.78 e Å⁻³
Δρ_min = −0.29 e Å⁻³

Data collection: APEX2 (Bruker, 2005 ); cell refinement: SAINT (Bruker, 2005); 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/S1600536809034138/tk2531sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809034138/tk2531Isup2.hkl

checkCIF report

Related literature top

For a review of indazoles, see: Elguéro (1996); Elguéro et al. (1995).

Experimental top

3-Chloro-6-nitroindazole (5 mmol) and allyl bromide (10 mmol) were reacted in THF (40 ml) in the presence of potassium carbonate (10 mmol) and tetra-n-butylammonium bromide (0.5 mmol). The mixture was stirred for 24 h, filtered, and the THF removed under vacuum. The product was separated by chromatography on silica gel with a hexane:ethyl acetate (9:1) solvent system. The compound was obtained as yellow crystals in 50% yield; m.p. 351 K.

Computing details top

Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT (Bruker, 2005); data reduction: SAINT (Bruker, 2005); 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).

Figures top

Fig. 1. Thermal ellipsoid plot (Barbour, 2001) of the two independent molecules of C₁₀H₈ClN₃O₂ at the 50% probability level; hydrogen atoms are drawn as spheres of arbitrary radius.

1-Allyl-3-chloro-6-nitro-1H-indazole top

Crystal data top

C₁₀H₈ClN₃O₂	F(000) = 976
M_r = 237.64	D_x = 1.458 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 6549 reflections
a = 7.6804 (1) Å	θ = 2.2–29.5°
b = 9.9559 (2) Å	µ = 0.34 mm⁻¹
c = 28.4344 (4) Å	T = 295 K
β = 95.144 (1)°	Prism, yellow
V = 2165.49 (6) Å³	0.4 × 0.3 × 0.2 mm
Z = 8

Data collection top

Bruker APEX2 diffractometer	3777 independent reflections
Radiation source: fine-focus sealed tube	2665 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.032
ϕ and ω scans	θ_max = 25.0°, θ_min = 1.4°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −9→9
T_min = 0.884, T_max = 0.934	k = −11→11
19833 measured reflections	l = −33→33

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)] = 0.056	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.185	H-atom parameters constrained
S = 1.07	w = 1/[σ²(F_o²) + (0.1031P)² + 0.7179P] where P = (F_o² + 2F_c²)/3
3777 reflections	(Δ/σ)_max = 0.001
289 parameters	Δρ_max = 0.78 e Å⁻³
0 restraints	Δρ_min = −0.29 e Å⁻³

Crystal data top

C₁₀H₈ClN₃O₂	V = 2165.49 (6) Å³
M_r = 237.64	Z = 8
Monoclinic, P2₁/n	Mo Kα radiation
a = 7.6804 (1) Å	µ = 0.34 mm⁻¹
b = 9.9559 (2) Å	T = 295 K
c = 28.4344 (4) Å	0.4 × 0.3 × 0.2 mm
β = 95.144 (1)°

Data collection top

Bruker APEX2 diffractometer	3777 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	2665 reflections with I > 2σ(I)
T_min = 0.884, T_max = 0.934	R_int = 0.032
19833 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.056	0 restraints
wR(F²) = 0.185	H-atom parameters constrained
S = 1.07	Δρ_max = 0.78 e Å⁻³
3777 reflections	Δρ_min = −0.29 e Å⁻³
289 parameters

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

	x	y	z	U_iso*/U_eq
Cl1	0.30814 (12)	0.06578 (10)	0.03474 (3)	0.0718 (3)
Cl2	0.94159 (18)	0.35838 (12)	0.02733 (4)	0.0958 (4)
O1	0.6481 (4)	0.0762 (3)	0.28950 (9)	0.0866 (9)
O2	0.7296 (4)	0.2788 (3)	0.27899 (9)	0.0867 (9)
O3	1.2186 (4)	0.2329 (4)	0.28256 (10)	0.1089 (11)
O4	1.0809 (4)	0.0460 (3)	0.27538 (10)	0.0928 (9)
N1	0.5287 (3)	0.3527 (3)	0.10386 (9)	0.0563 (7)
N2	0.4505 (4)	0.2960 (3)	0.06380 (9)	0.0606 (8)
N3	0.6601 (4)	0.1750 (3)	0.26458 (9)	0.0582 (7)
N4	0.8630 (3)	0.0501 (3)	0.09910 (10)	0.0529 (7)
N5	0.8504 (4)	0.1220 (3)	0.05846 (10)	0.0622 (8)
N6	1.1300 (4)	0.1509 (4)	0.25934 (11)	0.0659 (8)
C1	0.4072 (4)	0.1742 (4)	0.07565 (11)	0.0523 (8)
C2	0.4547 (3)	0.1450 (3)	0.12352 (11)	0.0451 (7)
C3	0.4413 (4)	0.0352 (3)	0.15351 (11)	0.0509 (8)
H3	0.3882	−0.0441	0.1424	0.061*
C4	0.5079 (4)	0.0470 (3)	0.19951 (11)	0.0510 (8)
H4	0.5003	−0.0244	0.2203	0.061*
C5	0.5876 (4)	0.1675 (3)	0.21511 (10)	0.0458 (7)
C6	0.6039 (4)	0.2781 (3)	0.18747 (10)	0.0447 (7)
H6	0.6570	0.3568	0.1991	0.054*
C7	0.5353 (4)	0.2648 (3)	0.14059 (11)	0.0447 (7)
C8	0.6026 (5)	0.4877 (4)	0.10227 (14)	0.0678 (10)
H8A	0.6737	0.5039	0.1317	0.081*
H8B	0.6793	0.4909	0.0770	0.081*
C9	0.4777 (6)	0.5939 (5)	0.0952 (2)	0.0994 (15)
H9	0.4034	0.6041	0.1191	0.119*
C10	0.4537 (7)	0.6752 (5)	0.0618 (2)	0.1091 (18)
H10A	0.5232	0.6710	0.0366	0.131*
H10B	0.3663	0.7398	0.0620	0.131*
C11	0.9279 (4)	0.2371 (4)	0.06933 (11)	0.0588 (9)
C12	0.9941 (4)	0.2448 (3)	0.11660 (11)	0.0488 (8)
C13	1.0839 (4)	0.3397 (3)	0.14605 (13)	0.0563 (8)
H13	1.1130	0.4232	0.1343	0.068*
C14	1.1278 (4)	0.3072 (4)	0.19233 (13)	0.0563 (9)
H14	1.1885	0.3681	0.2124	0.068*
C15	1.0808 (4)	0.1816 (3)	0.20921 (11)	0.0491 (8)
C16	0.9938 (3)	0.0852 (3)	0.18217 (11)	0.0453 (7)
H16	0.9651	0.0023	0.1944	0.054*
C17	0.9510 (3)	0.1194 (3)	0.13522 (11)	0.0435 (7)
C18	0.8035 (4)	−0.0888 (3)	0.09845 (13)	0.0615 (9)
H18A	0.6969	−0.0963	0.0776	0.074*
H18B	0.7766	−0.1142	0.1299	0.074*
C19	0.9352 (5)	−0.1820 (4)	0.08251 (14)	0.0701 (10)
H19	0.9748	−0.1658	0.0531	0.084*
C20	0.9988 (6)	−0.2813 (5)	0.1052 (2)	0.1019 (16)
H20A	0.9629	−0.3012	0.1348	0.122*
H20B	1.0817	−0.3350	0.0924	0.122*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.0785 (6)	0.0739 (7)	0.0602 (6)	−0.0018 (5)	−0.0089 (4)	−0.0182 (4)
Cl2	0.1491 (11)	0.0756 (9)	0.0649 (6)	0.0153 (7)	0.0215 (6)	0.0187 (5)
O1	0.128 (2)	0.072 (2)	0.0577 (15)	0.0029 (16)	−0.0050 (15)	0.0184 (15)
O2	0.116 (2)	0.081 (2)	0.0593 (16)	−0.0218 (17)	−0.0108 (15)	−0.0064 (14)
O3	0.126 (2)	0.121 (3)	0.0733 (19)	−0.021 (2)	−0.0282 (18)	−0.0127 (19)
O4	0.133 (3)	0.074 (2)	0.0688 (18)	0.0066 (18)	−0.0030 (16)	0.0176 (16)
N1	0.0649 (16)	0.0493 (18)	0.0536 (16)	−0.0039 (13)	−0.0018 (12)	0.0018 (13)
N2	0.0677 (16)	0.063 (2)	0.0494 (16)	0.0022 (14)	−0.0031 (13)	−0.0010 (14)
N3	0.0651 (16)	0.060 (2)	0.0495 (16)	0.0074 (14)	0.0058 (13)	−0.0029 (15)
N4	0.0516 (14)	0.0464 (18)	0.0606 (17)	0.0000 (12)	0.0055 (12)	−0.0086 (13)
N5	0.0684 (17)	0.062 (2)	0.0560 (17)	0.0127 (15)	0.0025 (13)	−0.0061 (15)
N6	0.0645 (17)	0.071 (2)	0.0614 (19)	0.0134 (16)	−0.0007 (15)	−0.0084 (18)
C1	0.0503 (16)	0.053 (2)	0.0530 (19)	0.0056 (14)	0.0033 (14)	−0.0088 (16)
C2	0.0388 (14)	0.043 (2)	0.0543 (18)	0.0061 (12)	0.0063 (13)	−0.0087 (14)
C3	0.0506 (16)	0.041 (2)	0.062 (2)	0.0009 (13)	0.0101 (14)	−0.0064 (16)
C4	0.0567 (17)	0.042 (2)	0.0556 (19)	0.0068 (14)	0.0119 (15)	0.0031 (15)
C5	0.0443 (15)	0.047 (2)	0.0469 (17)	0.0094 (13)	0.0072 (13)	−0.0022 (14)
C6	0.0449 (15)	0.0386 (19)	0.0504 (17)	0.0050 (12)	0.0027 (13)	−0.0055 (14)
C7	0.0414 (14)	0.0427 (19)	0.0503 (17)	0.0079 (13)	0.0066 (12)	−0.0006 (15)
C8	0.078 (2)	0.054 (2)	0.069 (2)	−0.0089 (19)	−0.0050 (18)	0.0130 (18)
C9	0.085 (3)	0.078 (3)	0.134 (4)	−0.011 (2)	0.000 (3)	0.021 (3)
C10	0.108 (3)	0.080 (4)	0.132 (4)	−0.019 (3)	−0.023 (3)	0.046 (3)
C11	0.072 (2)	0.050 (2)	0.055 (2)	0.0154 (17)	0.0094 (17)	0.0019 (16)
C12	0.0496 (16)	0.040 (2)	0.0581 (18)	0.0094 (13)	0.0139 (14)	−0.0024 (15)
C13	0.0630 (19)	0.036 (2)	0.072 (2)	−0.0020 (14)	0.0176 (17)	−0.0019 (16)
C14	0.0510 (16)	0.047 (2)	0.072 (2)	−0.0019 (14)	0.0107 (15)	−0.0194 (17)
C15	0.0446 (15)	0.045 (2)	0.0577 (19)	0.0105 (13)	0.0057 (14)	−0.0034 (15)
C16	0.0460 (15)	0.0322 (18)	0.0589 (18)	0.0040 (12)	0.0105 (13)	0.0000 (14)
C17	0.0389 (14)	0.0354 (18)	0.0567 (18)	0.0060 (12)	0.0075 (13)	−0.0060 (14)
C18	0.0579 (18)	0.050 (2)	0.077 (2)	−0.0065 (15)	0.0049 (16)	−0.0166 (18)
C19	0.085 (2)	0.056 (3)	0.072 (2)	0.001 (2)	0.0204 (19)	−0.002 (2)
C20	0.096 (3)	0.082 (4)	0.131 (4)	0.013 (3)	0.030 (3)	0.027 (3)

Geometric parameters (Å, º) top

Cl1—C1	1.714 (3)	C6—H6	0.9300
Cl2—C11	1.708 (4)	C8—C9	1.430 (6)
O1—N3	1.221 (4)	C8—H8A	0.9700
O2—N3	1.218 (4)	C8—H8B	0.9700
O3—N6	1.219 (4)	C9—C10	1.250 (6)
O4—N6	1.213 (4)	C9—H9	0.9300
N1—C7	1.360 (4)	C10—H10A	0.9300
N1—N2	1.362 (4)	C10—H10B	0.9300
N1—C8	1.461 (4)	C11—C12	1.396 (4)
N2—C1	1.309 (5)	C12—C13	1.402 (5)
N3—C5	1.468 (4)	C12—C17	1.408 (4)
N4—N5	1.356 (4)	C13—C14	1.368 (5)
N4—C17	1.365 (4)	C13—H13	0.9300
N4—C18	1.456 (4)	C14—C15	1.398 (5)
N5—C11	1.316 (5)	C14—H14	0.9300
N6—C15	1.474 (4)	C15—C16	1.367 (4)
C1—C2	1.408 (4)	C16—C17	1.388 (4)
C2—C3	1.396 (4)	C16—H16	0.9300
C2—C7	1.410 (4)	C18—C19	1.474 (5)
C3—C4	1.366 (4)	C18—H18A	0.9700
C3—H3	0.9300	C18—H18B	0.9700
C4—C5	1.401 (4)	C19—C20	1.255 (6)
C4—H4	0.9300	C19—H19	0.9300
C5—C6	1.365 (4)	C20—H20A	0.9300
C6—C7	1.395 (4)	C20—H20B	0.9300

C7—N1—N2	111.0 (3)	H8A—C8—H8B	107.5
C7—N1—C8	128.9 (3)	C10—C9—C8	129.6 (6)
N2—N1—C8	119.9 (3)	C10—C9—H9	115.2
C1—N2—N1	105.8 (3)	C8—C9—H9	115.2
O2—N3—O1	122.8 (3)	C9—C10—H10A	120.0
O2—N3—C5	118.9 (3)	C9—C10—H10B	120.0
O1—N3—C5	118.3 (3)	H10A—C10—H10B	120.0
N5—N4—C17	111.6 (3)	N5—C11—C12	113.1 (3)
N5—N4—C18	119.5 (3)	N5—C11—Cl2	120.4 (3)
C17—N4—C18	128.6 (3)	C12—C11—Cl2	126.5 (3)
C11—N5—N4	105.3 (3)	C11—C12—C13	136.8 (3)
O4—N6—O3	123.4 (4)	C11—C12—C17	103.6 (3)
O4—N6—C15	118.8 (3)	C13—C12—C17	119.5 (3)
O3—N6—C15	117.8 (4)	C14—C13—C12	118.7 (3)
N2—C1—C2	113.0 (3)	C14—C13—H13	120.6
N2—C1—Cl1	121.1 (3)	C12—C13—H13	120.6
C2—C1—Cl1	125.9 (3)	C13—C14—C15	119.6 (3)
C3—C2—C1	136.5 (3)	C13—C14—H14	120.2
C3—C2—C7	120.4 (3)	C15—C14—H14	120.2
C1—C2—C7	103.1 (3)	C16—C15—C14	124.3 (3)
C4—C3—C2	118.4 (3)	C16—C15—N6	117.9 (3)
C4—C3—H3	120.8	C14—C15—N6	117.8 (3)
C2—C3—H3	120.8	C15—C16—C17	115.5 (3)
C3—C4—C5	119.5 (3)	C15—C16—H16	122.2
C3—C4—H4	120.3	C17—C16—H16	122.2
C5—C4—H4	120.3	N4—C17—C16	131.2 (3)
C6—C5—C4	124.7 (3)	N4—C17—C12	106.4 (3)
C6—C5—N3	117.7 (3)	C16—C17—C12	122.4 (3)
C4—C5—N3	117.7 (3)	N4—C18—C19	112.2 (3)
C5—C6—C7	115.3 (3)	N4—C18—H18A	109.2
C5—C6—H6	122.4	C19—C18—H18A	109.2
C7—C6—H6	122.4	N4—C18—H18B	109.2
N1—C7—C6	131.1 (3)	C19—C18—H18B	109.2
N1—C7—C2	107.2 (3)	H18A—C18—H18B	107.9
C6—C7—C2	121.8 (3)	C20—C19—C18	125.7 (4)
C9—C8—N1	115.3 (3)	C20—C19—H19	117.1
C9—C8—H8A	108.5	C18—C19—H19	117.1
N1—C8—H8A	108.5	C19—C20—H20A	120.0
C9—C8—H8B	108.5	C19—C20—H20B	120.0
N1—C8—H8B	108.5	H20A—C20—H20B	120.0

C7—N1—N2—C1	0.7 (3)	N2—N1—C8—C9	70.4 (5)
C8—N1—N2—C1	176.4 (3)	N1—C8—C9—C10	−116.9 (5)
C17—N4—N5—C11	−1.0 (3)	N4—N5—C11—C12	0.3 (4)
C18—N4—N5—C11	−174.4 (3)	N4—N5—C11—Cl2	179.8 (2)
N1—N2—C1—C2	−0.2 (4)	N5—C11—C12—C13	−179.6 (3)
N1—N2—C1—Cl1	−178.6 (2)	Cl2—C11—C12—C13	0.9 (6)
N2—C1—C2—C3	−179.7 (3)	N5—C11—C12—C17	0.4 (3)
Cl1—C1—C2—C3	−1.4 (5)	Cl2—C11—C12—C17	−179.0 (2)
N2—C1—C2—C7	−0.3 (3)	C11—C12—C13—C14	−179.7 (3)
Cl1—C1—C2—C7	178.1 (2)	C17—C12—C13—C14	0.2 (4)
C1—C2—C3—C4	179.3 (3)	C12—C13—C14—C15	−0.7 (4)
C7—C2—C3—C4	0.0 (4)	C13—C14—C15—C16	0.9 (5)
C2—C3—C4—C5	−0.3 (4)	C13—C14—C15—N6	−179.7 (3)
C3—C4—C5—C6	0.5 (4)	O4—N6—C15—C16	−5.2 (4)
C3—C4—C5—N3	−179.0 (3)	O3—N6—C15—C16	174.8 (3)
O2—N3—C5—C6	0.7 (4)	O4—N6—C15—C14	175.4 (3)
O1—N3—C5—C6	−179.1 (3)	O3—N6—C15—C14	−4.6 (4)
O2—N3—C5—C4	−179.8 (3)	C14—C15—C16—C17	−0.5 (4)
O1—N3—C5—C4	0.4 (4)	N6—C15—C16—C17	−179.9 (2)
C4—C5—C6—C7	−0.5 (4)	N5—N4—C17—C16	−180.0 (3)
N3—C5—C6—C7	179.0 (2)	C18—N4—C17—C16	−7.3 (5)
N2—N1—C7—C6	179.3 (3)	N5—N4—C17—C12	1.3 (3)
C8—N1—C7—C6	4.0 (5)	C18—N4—C17—C12	174.0 (3)
N2—N1—C7—C2	−0.8 (3)	C15—C16—C17—N4	−178.6 (3)
C8—N1—C7—C2	−176.1 (3)	C15—C16—C17—C12	0.0 (4)
C5—C6—C7—N1	−180.0 (3)	C11—C12—C17—N4	−1.0 (3)
C5—C6—C7—C2	0.2 (4)	C13—C12—C17—N4	179.0 (3)
C3—C2—C7—N1	−179.8 (3)	C11—C12—C17—C16	−179.9 (3)
C1—C2—C7—N1	0.7 (3)	C13—C12—C17—C16	0.2 (4)
C3—C2—C7—C6	0.1 (4)	N5—N4—C18—C19	81.6 (4)
C1—C2—C7—C6	−179.5 (3)	C17—N4—C18—C19	−90.5 (4)
C7—N1—C8—C9	−114.7 (4)	N4—C18—C19—C20	123.4 (5)

Experimental details

Crystal data
Chemical formula	C₁₀H₈ClN₃O₂
M_r	237.64
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	295
a, b, c (Å)	7.6804 (1), 9.9559 (2), 28.4344 (4)
β (°)	95.144 (1)
V (Å³)	2165.49 (6)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.34
Crystal size (mm)	0.4 × 0.3 × 0.2

Data collection
Diffractometer	Bruker APEX2 diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.884, 0.934
No. of measured, independent and observed [I > 2σ(I)] reflections	19833, 3777, 2665
R_int	0.032
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.056, 0.185, 1.07
No. of reflections	3777
No. of parameters	289
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.78, −0.29

Computer programs: APEX2 (Bruker, 2005), SAINT (Bruker, 2005), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), X-SEED (Barbour, 2001), publCIF (Westrip, 2009).

Acknowledgements

We thank Université Mohammed V-Agdal and the University of Malaya for supporting this study.

References

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