N,N′-Bis(4-bromo­benzyl­idene)-2,2-dimethyl­propane-1,3-diamine

Kia, R.; Fun, H.-K.; Kargar, H.

doi:10.1107/S1600536809008113

organic compounds

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ISSN: 2056-9890

Volume 65| Part 4| April 2009| Page o747

doi:10.1107/S1600536809008113

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N,N′-Bis(4-bromobenzylidene)-2,2-dimethylpropane-1,3-diamine

Reza Kia,^a Hoong-Kun Fun ^a ^* and Hadi Kargar ^b

^aX-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia, and ^bDepartment of Chemistry, School of Science, Payame Noor University (PNU), Ardakan, Yazd, Iran
^*Correspondence e-mail: hkfun@usm.my

(Received 2 March 2009; accepted 5 March 2009; online 14 March 2009)

The molecule of the title compound, C₁₉H₂₀Br₂N₂, is a potential bidentate Schiff base ligand. The two benzene rings are inclined at a dihedral angle of 30.85 (8)°. An interesting feature of the crystal structure is a weak intermolecular Br⋯Br [3.4752 (4) Å] interaction which is shorter than the sum of the van der Waals radii of the Br atoms and links neighbouring molecules into chains along the c axis. The crystal structure is further stabilized by intermolecular C—H⋯π interactions.

Related literature

For details of hydrogen-bond motifs, see: Bernstein et al. (1995 ). For related structure see, for example: Li et al. (2005 ); Bomfim et al. (2005 ); Glidewell et al. (2005 , 2006 ); Sun et al. (2004 ); Fun et al. (2008 ). For the stability of the temperature controller used for the data collection, see: Cosier & Glazer (1986 ).

Experimental

Crystal data

C₁₉H₂₀Br₂N₂
M_r = 436.19
Orthorhombic, P 2₁ 2₁ 2₁
a = 5.6687 (1) Å
b = 7.7919 (2) Å
c = 41.5932 (9) Å
V = 1837.17 (7) Å³
Z = 4
Mo Kα radiation
μ = 4.41 mm⁻¹
T = 100 K
0.45 × 0.44 × 0.12 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2005 ) T_min = 0.229, T_max = 0.586
38732 measured reflections
9454 independent reflections
7585 reflections with I > 2σ(I)
R_int = 0.049

Refinement

R[F² > 2σ(F²)] = 0.037
wR(F²) = 0.079
S = 1.03
9454 reflections
208 parameters
H-atom parameters constrained
Δρ_max = 1.04 e Å⁻³
Δρ_min = −0.61 e Å⁻³
Absolute structure: Flack (1983 ), 3971 Friedel pairs
Flack parameter: 0.019 (6)

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C4—H4A⋯Cg1ⁱ	0.95	2.85	3.5630 (18)	132
C13—H13A⋯Cg2ⁱⁱ	0.95	2.74	3.4648 (18)	134
Symmetry codes: (i) $[x+{\script{7\over 2}}, -y+{\script{1\over 2}}, -z+1]$ ; (ii) $[-x-1, y+{\script{1\over 2}}, -z+{\script{5\over 2}}]$ . Cg1 and Cg2 are the centroids of the C1–C6 and C9–C17 benzene rings, respectively.

Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT (Bruker, 2005); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809008113/at2737sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809008113/at2737Isup2.hkl

checkCIF report

Comment top

Schiff bases are one of most prevalent mixed-donor ligands in the field of coordination chemistry. They play an important role in the development of coordination chemistry related to catalysis and enzymatic reactions, magnetism, and supramolecular architectures. Structures of Schiff bases derived from substituted benzaldehydes and closely related to the title compound have been reported previously (Li et al., 2005; Bomfim et al., 2005; Glidewell et al., 2005, 2006; Sun et al., 2004; Fun et al., 2008).

In the title compound, Fig. 1, intramolecular C—H···N hydrogen bonds forms five-membered rings, producing S(5) ring motifs (Bernstein et al., 1995). The two benzene rings make a dihedral angle of 30.85 (8)°. The crystal structure is further stabilized by weak intermolecular C—H···π interactions [Cg1 and Cg2 are the centroids of the C1–C6 and C12–C17 benzene rings] (Table 1). The interesting feature of the crystal structure is weak intermolecular Br···Br [3.4752 (4) Å; symmetry code: 5/2 - x, 1 - y, -1/2 + z] interaction which is shorter than the sum of the van der Waals radius of Br atoms and link neighbouring molecules into chains along the c axis (Fig. 2).

Related literature top

For details of hydrogen-bond motifs, see: Bernstein et al. (1995). For the Flack parameter see, Flack (1983). For related structure see, for example: Li et al. (2005); Bomfim et al. (2005); Glidewell et al. (2005, 2006); Sun et al. (2004); Fun et al. (2008). For stability of the temperature controller used for data collection, see: Cosier & Glazer (1986). Cg1 and Cg2 are the centroids of the C1–C6 and C9–C17 benzene rings, respectively.

Experimental top

The synthetic method has been described earlier (Fun et al., 2008), except that 4-bromobenzaldehyde was used. Single crystals suitable for X-ray diffraction were obtained by evaporation of an ethanol solution at room temperature.

Computing details top

Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT (Bruker, 2005; data reduction: SAINT (Bruker, 2005); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).

Figures top

	Fig. 1. The molecular structure of the title compound with atom labels and 50% probability ellipsoids for non-H atoms. Intramolecular hydrogen bond is shown as dashed line.
	Fig. 2. The crystal packing of the title compound, viewed down the a- axis showing chains along the c-axis by Br···Br interactions.

N,N'-Bis(4-bromobenzylidene)-2,2-dimethylpropane-1,3-diamine top

Crystal data top

C₁₉H₂₀Br₂N₂	F(000) = 872
M_r = 436.19	D_x = 1.577 Mg m⁻³
Orthorhombic, P2₁2₁2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 9987 reflections
a = 5.6687 (1) Å	θ = 2.7–35.5°
b = 7.7919 (2) Å	µ = 4.41 mm⁻¹
c = 41.5932 (9) Å	T = 100 K
V = 1837.17 (7) Å³	Block, colourless
Z = 4	0.45 × 0.44 × 0.12 mm

Data collection top

Bruker SMART APEXII CCD area-detector diffractometer	9454 independent reflections
Radiation source: fine-focus sealed tube	7585 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.049
ϕ and ω scans	θ_max = 37.5°, θ_min = 2.0°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −9→9
T_min = 0.229, T_max = 0.586	k = −10→13
38732 measured reflections	l = −71→55

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.037	H-atom parameters constrained
wR(F²) = 0.079	w = 1/[σ²(F_o²) + (0.0316P)² + 0.2032P] where P = (F_o² + 2F_c²)/3
S = 1.03	(Δ/σ)_max = 0.011
9454 reflections	Δρ_max = 1.04 e Å⁻³
208 parameters	Δρ_min = −0.61 e Å⁻³
0 restraints	Absolute structure: Flack (1983), 3971 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.019 (6)

Crystal data top

C₁₉H₂₀Br₂N₂	V = 1837.17 (7) Å³
M_r = 436.19	Z = 4
Orthorhombic, P2₁2₁2₁	Mo Kα radiation
a = 5.6687 (1) Å	µ = 4.41 mm⁻¹
b = 7.7919 (2) Å	T = 100 K
c = 41.5932 (9) Å	0.45 × 0.44 × 0.12 mm

Data collection top

Bruker SMART APEXII CCD area-detector diffractometer	9454 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2005)	7585 reflections with I > 2σ(I)
T_min = 0.229, T_max = 0.586	R_int = 0.049
38732 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.037	H-atom parameters constrained
wR(F²) = 0.079	Δρ_max = 1.04 e Å⁻³
S = 1.03	Δρ_min = −0.61 e Å⁻³
9454 reflections	Absolute structure: Flack (1983), 3971 Friedel pairs
208 parameters	Absolute structure parameter: 0.019 (6)
0 restraints

Special details top

Experimental. The crystal was placed in the cold stream of an Oxford Cyrosystems Cobra open-flow nitrogen cryostat (Cosier & Glazer, 1986) operating at 100.0 (1) K.

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
Br1	1.59060 (4)	0.70918 (3)	0.679860 (5)	0.03041 (5)
Br2	1.02132 (3)	0.35735 (2)	1.095005 (4)	0.02216 (4)
N1	0.9734 (3)	0.7039 (2)	0.82239 (4)	0.0214 (3)
N2	0.8180 (3)	0.6175 (2)	0.93830 (4)	0.0198 (3)
C1	1.0509 (3)	0.5599 (2)	0.74067 (5)	0.0203 (3)
H1A	0.9062	0.4991	0.7388	0.024*
C2	1.1894 (4)	0.5835 (3)	0.71353 (5)	0.0219 (3)
H2A	1.1410	0.5403	0.6932	0.026*
C3	1.4013 (3)	0.6720 (2)	0.71684 (4)	0.0212 (3)
C4	1.4767 (3)	0.7348 (2)	0.74652 (4)	0.0197 (3)
H4A	1.6230	0.7935	0.7484	0.024*
C5	1.3353 (3)	0.7104 (3)	0.77327 (4)	0.0184 (3)
H5A	1.3848	0.7528	0.7936	0.022*
C6	1.1191 (3)	0.6235 (2)	0.77059 (4)	0.0180 (3)
C7	0.9574 (3)	0.6067 (2)	0.79820 (5)	0.0198 (3)
H7A	0.8386	0.5208	0.7978	0.024*
C8	0.8001 (3)	0.6814 (3)	0.84805 (4)	0.0209 (3)
H8A	0.6996	0.5808	0.8432	0.025*
H8B	0.6972	0.7839	0.8491	0.025*
C9	0.9225 (3)	0.6548 (2)	0.88094 (4)	0.0179 (3)
C10	0.7242 (3)	0.6457 (2)	0.90606 (4)	0.0188 (3)
H10A	0.6333	0.7542	0.9057	0.023*
H10B	0.6152	0.5510	0.9005	0.023*
C11	0.6955 (3)	0.5293 (2)	0.95790 (4)	0.0178 (3)
H11A	0.5486	0.4841	0.9509	0.021*
C12	0.7732 (3)	0.4951 (2)	0.99097 (4)	0.0165 (3)
C13	0.6324 (3)	0.3938 (2)	1.01110 (5)	0.0184 (3)
H13A	0.4861	0.3514	1.0033	0.022*
C14	0.7025 (3)	0.3543 (3)	1.04224 (4)	0.0196 (3)
H14A	0.6050	0.2867	1.0558	0.024*
C15	0.9177 (3)	0.4158 (2)	1.05301 (4)	0.0184 (3)
C16	1.0606 (3)	0.5189 (2)	1.03375 (4)	0.0192 (3)
H16A	1.2063	0.5616	1.0417	0.023*
C17	0.9877 (3)	0.5583 (2)	1.00290 (4)	0.0193 (3)
H17A	1.0838	0.6289	0.9897	0.023*
C18	1.0856 (3)	0.8053 (3)	0.88844 (5)	0.0241 (4)
H18A	1.1615	0.7866	0.9093	0.036*
H18B	0.9935	0.9117	0.8891	0.036*
H18C	1.2065	0.8142	0.8717	0.036*
C19	1.0619 (4)	0.4868 (3)	0.88061 (5)	0.0244 (4)
H19A	1.1393	0.4706	0.9015	0.037*
H19B	1.1816	0.4913	0.8636	0.037*
H19C	0.9544	0.3908	0.8765	0.037*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Br1	0.02919 (10)	0.04538 (12)	0.01667 (8)	0.00266 (9)	0.00467 (7)	0.00429 (9)
Br2	0.02804 (9)	0.02117 (7)	0.01728 (8)	−0.00042 (7)	−0.00430 (7)	0.00085 (7)
N1	0.0223 (6)	0.0248 (7)	0.0169 (6)	−0.0017 (6)	0.0014 (6)	0.0021 (6)
N2	0.0204 (7)	0.0234 (8)	0.0155 (7)	0.0001 (6)	0.0011 (5)	0.0003 (6)
C1	0.0215 (8)	0.0207 (8)	0.0189 (8)	0.0001 (6)	−0.0015 (6)	−0.0033 (6)
C2	0.0239 (8)	0.0251 (8)	0.0168 (8)	0.0028 (7)	−0.0041 (7)	−0.0041 (7)
C3	0.0228 (7)	0.0233 (9)	0.0176 (8)	0.0044 (6)	0.0029 (6)	0.0023 (6)
C4	0.0183 (7)	0.0218 (7)	0.0190 (7)	−0.0006 (6)	0.0004 (6)	0.0019 (6)
C5	0.0194 (7)	0.0208 (8)	0.0150 (7)	−0.0003 (7)	−0.0011 (6)	−0.0011 (7)
C6	0.0209 (7)	0.0170 (8)	0.0161 (7)	0.0012 (6)	0.0000 (6)	0.0006 (6)
C7	0.0178 (7)	0.0216 (8)	0.0199 (8)	−0.0008 (6)	−0.0005 (6)	0.0034 (6)
C8	0.0181 (7)	0.0277 (10)	0.0168 (8)	−0.0001 (6)	0.0012 (6)	0.0024 (7)
C9	0.0160 (7)	0.0201 (7)	0.0175 (7)	0.0003 (6)	0.0006 (5)	0.0009 (6)
C10	0.0186 (7)	0.0221 (7)	0.0157 (7)	−0.0007 (6)	−0.0008 (6)	0.0019 (8)
C11	0.0191 (7)	0.0186 (8)	0.0157 (7)	−0.0003 (6)	0.0002 (6)	−0.0017 (6)
C12	0.0181 (7)	0.0161 (7)	0.0152 (7)	0.0006 (6)	0.0006 (6)	−0.0013 (6)
C13	0.0166 (7)	0.0197 (8)	0.0189 (8)	−0.0009 (6)	0.0002 (6)	−0.0003 (6)
C14	0.0206 (7)	0.0205 (7)	0.0178 (8)	−0.0013 (7)	0.0020 (6)	0.0015 (7)
C15	0.0226 (8)	0.0186 (7)	0.0141 (7)	0.0027 (6)	−0.0013 (6)	−0.0020 (6)
C16	0.0176 (8)	0.0191 (7)	0.0208 (8)	−0.0016 (6)	0.0004 (6)	−0.0026 (6)
C17	0.0206 (7)	0.0192 (7)	0.0180 (7)	−0.0022 (7)	0.0004 (7)	−0.0009 (6)
C18	0.0212 (8)	0.0259 (9)	0.0251 (9)	−0.0045 (7)	0.0019 (7)	−0.0011 (8)
C19	0.0246 (9)	0.0235 (8)	0.0250 (9)	0.0057 (7)	0.0037 (7)	0.0021 (7)

Geometric parameters (Å, º) top

Br1—C3	1.8978 (19)	C9—C19	1.529 (3)
Br2—C15	1.8983 (18)	C9—C10	1.536 (2)
N1—C7	1.263 (2)	C10—H10A	0.9900
N1—C8	1.462 (2)	C10—H10B	0.9900
N2—C11	1.272 (2)	C11—C12	1.469 (3)
N2—C10	1.459 (2)	C11—H11A	0.9500
C1—C2	1.387 (3)	C12—C13	1.400 (3)
C1—C6	1.394 (3)	C12—C17	1.402 (3)
C1—H1A	0.9500	C13—C14	1.389 (3)
C2—C3	1.392 (3)	C13—H13A	0.9500
C2—H2A	0.9500	C14—C15	1.385 (3)
C3—C4	1.395 (3)	C14—H14A	0.9500
C4—C5	1.384 (2)	C15—C16	1.394 (3)
C4—H4A	0.9500	C16—C17	1.383 (3)
C5—C6	1.404 (3)	C16—H16A	0.9500
C5—H5A	0.9500	C17—H17A	0.9500
C6—C7	1.475 (3)	C18—H18A	0.9800
C7—H7A	0.9500	C18—H18B	0.9800
C8—C9	1.548 (3)	C18—H18C	0.9800
C8—H8A	0.9900	C19—H19A	0.9800
C8—H8B	0.9900	C19—H19B	0.9800
C9—C18	1.525 (3)	C19—H19C	0.9800

C7—N1—C8	117.50 (17)	C9—C10—H10A	109.3
C11—N2—C10	118.11 (16)	N2—C10—H10B	109.3
C2—C1—C6	121.48 (17)	C9—C10—H10B	109.3
C2—C1—H1A	119.3	H10A—C10—H10B	108.0
C6—C1—H1A	119.3	N2—C11—C12	122.30 (17)
C1—C2—C3	118.26 (18)	N2—C11—H11A	118.9
C1—C2—H2A	120.9	C12—C11—H11A	118.9
C3—C2—H2A	120.9	C13—C12—C17	118.72 (17)
C2—C3—C4	121.73 (18)	C13—C12—C11	119.43 (16)
C2—C3—Br1	118.89 (15)	C17—C12—C11	121.84 (17)
C4—C3—Br1	119.37 (14)	C14—C13—C12	121.29 (17)
C5—C4—C3	119.03 (17)	C14—C13—H13A	119.4
C5—C4—H4A	120.5	C12—C13—H13A	119.4
C3—C4—H4A	120.5	C15—C14—C13	118.47 (17)
C4—C5—C6	120.53 (16)	C15—C14—H14A	120.8
C4—C5—H5A	119.7	C13—C14—H14A	120.8
C6—C5—H5A	119.7	C14—C15—C16	121.70 (17)
C1—C6—C5	118.96 (16)	C14—C15—Br2	119.15 (14)
C1—C6—C7	119.40 (17)	C16—C15—Br2	119.15 (14)
C5—C6—C7	121.56 (16)	C17—C16—C15	119.17 (17)
N1—C7—C6	121.50 (17)	C17—C16—H16A	120.4
N1—C7—H7A	119.3	C15—C16—H16A	120.4
C6—C7—H7A	119.3	C16—C17—C12	120.63 (17)
N1—C8—C9	111.10 (15)	C16—C17—H17A	119.7
N1—C8—H8A	109.4	C12—C17—H17A	119.7
C9—C8—H8A	109.4	C9—C18—H18A	109.5
N1—C8—H8B	109.4	C9—C18—H18B	109.5
C9—C8—H8B	109.4	H18A—C18—H18B	109.5
H8A—C8—H8B	108.0	C9—C18—H18C	109.5
C18—C9—C19	110.28 (15)	H18A—C18—H18C	109.5
C18—C9—C10	109.88 (15)	H18B—C18—H18C	109.5
C19—C9—C10	110.16 (15)	C9—C19—H19A	109.5
C18—C9—C8	110.46 (16)	C9—C19—H19B	109.5
C19—C9—C8	109.78 (16)	H19A—C19—H19B	109.5
C10—C9—C8	106.20 (14)	C9—C19—H19C	109.5
N2—C10—C9	111.43 (14)	H19A—C19—H19C	109.5
N2—C10—H10A	109.3	H19B—C19—H19C	109.5

C6—C1—C2—C3	0.4 (3)	C11—N2—C10—C9	−146.93 (17)
C1—C2—C3—C4	0.7 (3)	C18—C9—C10—N2	−61.5 (2)
C1—C2—C3—Br1	−178.88 (14)	C19—C9—C10—N2	60.2 (2)
C2—C3—C4—C5	−0.9 (3)	C8—C9—C10—N2	178.99 (16)
Br1—C3—C4—C5	178.64 (14)	C10—N2—C11—C12	−179.41 (16)
C3—C4—C5—C6	0.1 (3)	N2—C11—C12—C13	−178.58 (17)
C2—C1—C6—C5	−1.2 (3)	N2—C11—C12—C17	0.2 (3)
C2—C1—C6—C7	175.36 (17)	C17—C12—C13—C14	−0.6 (3)
C4—C5—C6—C1	0.9 (3)	C11—C12—C13—C14	178.16 (17)
C4—C5—C6—C7	−175.54 (17)	C12—C13—C14—C15	−0.8 (3)
C8—N1—C7—C6	177.89 (16)	C13—C14—C15—C16	1.7 (3)
C1—C6—C7—N1	−157.81 (18)	C13—C14—C15—Br2	−178.06 (14)
C5—C6—C7—N1	18.7 (3)	C14—C15—C16—C17	−1.2 (3)
C7—N1—C8—C9	126.29 (18)	Br2—C15—C16—C17	178.54 (14)
N1—C8—C9—C18	57.0 (2)	C15—C16—C17—C12	−0.2 (3)
N1—C8—C9—C19	−64.8 (2)	C13—C12—C17—C16	1.1 (3)
N1—C8—C9—C10	176.10 (15)	C11—C12—C17—C16	−177.63 (17)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C18—H18C···N1	0.98	2.59	2.929 (3)	101
C4—H4A···Cg1ⁱ	0.95	2.85	3.5630 (18)	132
C13—H13A···Cg2ⁱⁱ	0.95	2.74	3.4648 (18)	134

Symmetry codes: (i) x+7/2, −y+1/2, −z+1; (ii) −x−1, y+1/2, −z+5/2.

Experimental details

Crystal data
Chemical formula	C₁₉H₂₀Br₂N₂
M_r	436.19
Crystal system, space group	Orthorhombic, P2₁2₁2₁
Temperature (K)	100
a, b, c (Å)	5.6687 (1), 7.7919 (2), 41.5932 (9)
V (Å³)	1837.17 (7)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	4.41
Crystal size (mm)	0.45 × 0.44 × 0.12

Data collection
Diffractometer	Bruker SMART APEXII CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2005)
T_min, T_max	0.229, 0.586
No. of measured, independent and observed [I > 2σ(I)] reflections	38732, 9454, 7585
R_int	0.049
(sin θ/λ)_max (Å⁻¹)	0.857

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.037, 0.079, 1.03
No. of reflections	9454
No. of parameters	208
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	1.04, −0.61
Absolute structure	Flack (1983), 3971 Friedel pairs
Absolute structure parameter	0.019 (6)

Computer programs: APEX2 (Bruker, 2005), SAINT (Bruker, 2005), SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C18—H18C···N1	0.9800	2.5900	2.929 (3)	101.00
C4—H4A···Cg1ⁱ	0.9500	2.8500	3.5630 (18)	132.00
C13—H13A···Cg2ⁱⁱ	0.9500	2.7400	3.4648 (18)	134.00

Symmetry codes: (i) x+7/2, −y+1/2, −z+1; (ii) −x−1, y+1/2, −z+5/2.

Acknowledgements

HKF and RK thank the Malaysian Government and Universiti Sains Malaysia for the Science Fund grant No. 305/PFIZIK/613312. RK thanks Universiti Sains Malaysia for a post-doctoral research fellowship. HK thanks PNU for financial support. HKF also thanks Universiti Sains Malaysia for the Research University Golden Goose grant No. 1001/PFIZIK/811012.

References

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