(E)-4-Bromo-2-[(2,6-diisopropyl­phen­yl)imino­meth­yl]phenol

Balamurugan, P.; Raja, K.K.; Rani, S.K.; Chakkaravarthi, G.; Rajagopal, G.

doi:10.1107/S1600536812021605

organic compounds

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ISSN: 2056-9890

Volume 68| Part 6| June 2012| Page o1782

doi:10.1107/S1600536812021605

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(E)-4-Bromo-2-[(2,6-diisopropylphenyl)iminomethyl]phenol

P. Balamurugan,^a K. Kanmani Raja,^b S. Kutti Rani,^c G. Chakkaravarthi ^d ^* and G. Rajagopal ^e ^*

^aDepartment of Chemistry, Government Arts College (Men), Nandanam, Chennai 600 035, India, ^bDepartment of Chemistry, Government Thirumagal Mills College, Gudiyattam 632 604, India, ^cDepartment of Chemistry, B.S. Abdur Rahman University, Vandalur, Chennai 600 049, India, ^dDepartment of Physics, CPCL Polytechnic College, Chennai 600 068, India, and ^eDepartment of Chemistry, Government Arts College, Melur 625 106, India
^*Correspondence e-mail: chakkaravarthi_2005@yahoo.com, rajagopal18@yahoo.com

(Received 11 May 2012; accepted 13 May 2012; online 19 May 2012)

In the title compound, C₁₉H₂₂BrNO, the dihedral angle between the benzene rings is 76.17 (14)° and an intramolecular O—H⋯N hydrogen bond with an S(6) graph-set motif is present. One methyl group is disordered over two sets of sites with site occupancies of 0.66 (3) and 0.34 (3). A weak intermolecular C—H⋯π interaction is observed in the crystal structure.

Related literature

For the biological activity of Schiff base ligands, see: Daier et al. (2004 ); Santos et al. (2001 ). For related structures, see: Raja et al. (2008 ); Lin et al. (2005 ).

Experimental

Crystal data

C₁₉H₂₂BrNO
M_r = 360.29
Orthorhombic, P 2₁ 2₁ 2₁
a = 6.1851 (12) Å
b = 12.759 (3) Å
c = 22.698 (5) Å
V = 1791.3 (6) Å³
Z = 4
Mo Kα radiation
μ = 2.30 mm⁻¹
T = 295 K
0.24 × 0.22 × 0.18 mm

Data collection

Bruker Kappa APEXII diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.609, T_max = 0.683
23590 measured reflections
5107 independent reflections
3242 reflections with I > 2σ(I)
R_int = 0.039

Refinement

R[F² > 2σ(F²)] = 0.040
wR(F²) = 0.100
S = 1.01
5107 reflections
214 parameters
H-atom parameters constrained
Δρ_max = 0.38 e Å⁻³
Δρ_min = −0.22 e Å⁻³
Absolute structure: Flack (1983 ), 2179 Friedel pairs
Flack parameter: 0.011 (10)

Table 1
Hydrogen-bond geometry (Å, °)

Cg2 is the centroid of the C14–C19 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯N1	0.82	1.87	2.597 (3)	147
C16—H16⋯Cg2ⁱ	0.93	2.86	3.522 (3)	129
Symmetry code: (i) $[-x, y+{\script{1\over 2}}, -z+{\script{5\over 2}}]$ .

Data collection: APEX2 (Bruker, 2004 ); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009 ); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536812021605/is5140sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812021605/is5140Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536812021605/is5140Isup3.cml

checkCIF report

Comment top

Schiff base derivatives are known to exhibit catalytic (Daier et al., 2004), antibacterial, antitumor and antitoxic (Santos et al., 2001) activities. The geometric parameters in the title compound are comparable with the similar reported structures (Raja et al., 2008; Lin et al., 2005). The dihedral angle between the aromatic rings (C1–C6) and (C14–C19) is 76.17 (14)°. One of the methyl groups in the molecule is disordered over two positions with site occupancies of 0.66 (3) and 0.34 (3). The molecule adopts an anti-periplanar [C1—N1—C13—C14 = -179.5 (2)°] conformation about the C=N double bond. The molecular structure is stabilized by an intramolecular O—H···N hydrogen bond and the crystal structure exhibit a weak intermolecular C—H···π (Table 1 ) interaction.

Related literature top

For the biological activity of Schiff base ligands, see: Daier et al. (2004); Santos et al. (2001). For related structures, see: Raja et al. (2008); Lin et al. (2005).

Experimental top

An ethanolic solution (10 ml) of 2,6-diisopropylaniline (2 mmol) was magnetically stirred in a round bottom flask followed by drop wise addition of ethanolic solution (10 ml) of 5-bromosalicylaldehyde (2 mmol). The reaction mixture was then refluxed for 3 h and upon cooling to 273 K, a yellow solid precipitated from the reaction mixture. The solid which separated out was filtered, washed with ice cold ethanol and dried over anhydrous CaCl₂. Single crystal of good diffraction quality was obtained by the recrystallization of compound with the ethanol solution by slow evaporation method. Yield: 70%.

Computing details top

Data collection: APEX2 (Bruker, 2004); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT (Bruker, 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

Fig. 1. The molecular structure of the title compound, with atom labels and 30% probability displacement ellipsoids for non-H atoms.

(E)-4-Bromo-2-[(2,6-diisopropylphenyl)iminomethyl]phenol top

Crystal data top

C₁₉H₂₂BrNO	F(000) = 744
M_r = 360.29	D_x = 1.336 Mg m⁻³
Orthorhombic, P2₁2₁2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 2359 reflections
a = 6.1851 (12) Å	θ = 1.8–29.8°
b = 12.759 (3) Å	µ = 2.30 mm⁻¹
c = 22.698 (5) Å	T = 295 K
V = 1791.3 (6) Å³	Prism, light yellow
Z = 4	0.24 × 0.22 × 0.18 mm

Data collection top

Bruker Kappa APEXII diffractometer	5107 independent reflections
Radiation source: fine-focus sealed tube	3242 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.039
ω and ϕ scans	θ_max = 29.8°, θ_min = 1.8°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −8→8
T_min = 0.609, T_max = 0.683	k = −17→11
23590 measured reflections	l = −30→31

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)] = 0.040	H-atom parameters constrained
wR(F²) = 0.100	w = 1/[σ²(F_o²) + (0.0449P)² + 0.1641P] where P = (F_o² + 2F_c²)/3
S = 1.01	(Δ/σ)_max < 0.001
5107 reflections	Δρ_max = 0.38 e Å⁻³
214 parameters	Δρ_min = −0.22 e Å⁻³
0 restraints	Absolute structure: Flack (1983), 2179 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.011 (10)

Crystal data top

C₁₉H₂₂BrNO	V = 1791.3 (6) Å³
M_r = 360.29	Z = 4
Orthorhombic, P2₁2₁2₁	Mo Kα radiation
a = 6.1851 (12) Å	µ = 2.30 mm⁻¹
b = 12.759 (3) Å	T = 295 K
c = 22.698 (5) Å	0.24 × 0.22 × 0.18 mm

Data collection top

Bruker Kappa APEXII diffractometer	5107 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	3242 reflections with I > 2σ(I)
T_min = 0.609, T_max = 0.683	R_int = 0.039
23590 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.040	H-atom parameters constrained
wR(F²) = 0.100	Δρ_max = 0.38 e Å⁻³
S = 1.01	Δρ_min = −0.22 e Å⁻³
5107 reflections	Absolute structure: Flack (1983), 2179 Friedel pairs
214 parameters	Absolute structure parameter: 0.011 (10)
0 restraints

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

	x	y	z	U_iso*/U_eq	Occ. (<1)
Br1	0.52689 (6)	0.49239 (2)	0.950698 (17)	0.07970 (14)
O1	1.1558 (3)	0.14355 (16)	0.90753 (9)	0.0593 (5)
H1	1.1027	0.0973	0.8870	0.089*
N1	0.8534 (3)	0.04639 (16)	0.84992 (9)	0.0439 (5)
C1	0.7847 (4)	−0.0403 (2)	0.81528 (12)	0.0454 (6)
C2	0.6525 (5)	−0.1178 (2)	0.83940 (14)	0.0579 (7)
C3	0.6048 (6)	−0.2032 (2)	0.80436 (16)	0.0747 (10)
H3	0.5181	−0.2565	0.8192	0.090*
C4	0.6846 (7)	−0.2105 (3)	0.74734 (17)	0.0814 (11)
H4	0.6517	−0.2690	0.7246	0.098*
C5	0.8084 (6)	−0.1344 (3)	0.72451 (16)	0.0736 (10)
H5	0.8562	−0.1399	0.6858	0.088*
C6	0.8666 (5)	−0.0472 (2)	0.75789 (13)	0.0542 (7)
C7	0.5681 (6)	−0.1119 (2)	0.90207 (15)	0.0744 (10)
H7	0.5856	−0.0393	0.9154	0.089*
C8	0.7009 (9)	−0.1799 (5)	0.94217 (19)	0.1273 (19)
H8A	0.6944	−0.2512	0.9288	0.191*
H8B	0.6448	−0.1756	0.9815	0.191*
H8C	0.8483	−0.1563	0.9418	0.191*
C9	0.3341 (7)	−0.1387 (5)	0.9075 (2)	0.1205 (18)
H9A	0.2865	−0.1250	0.9470	0.181*
H9B	0.3135	−0.2115	0.8986	0.181*
H9C	0.2519	−0.0968	0.8805	0.181*
C10	1.0109 (5)	0.0367 (2)	0.73253 (13)	0.0632 (7)
H10A	1.0195	0.0961	0.7598	0.076*	0.66 (3)
H10B	1.0424	0.0756	0.7688	0.076*	0.34 (3)
C11	0.933 (2)	0.0755 (10)	0.6705 (6)	0.097 (3)	0.66 (3)
H11A	0.7786	0.0838	0.6708	0.145*	0.66 (3)
H11B	0.9724	0.0249	0.6411	0.145*	0.66 (3)
H11C	0.9998	0.1415	0.6616	0.145*	0.66 (3)
C11A	0.884 (2)	0.114 (2)	0.7024 (16)	0.090 (8)	0.34 (3)
H11D	0.9780	0.1663	0.6856	0.135*	0.34 (3)
H11E	0.7874	0.1474	0.7299	0.135*	0.34 (3)
H11F	0.8016	0.0816	0.6717	0.135*	0.34 (3)
C12	1.2339 (6)	−0.0035 (5)	0.7194 (3)	0.1209 (16)
H12A	1.2247	−0.0607	0.6920	0.181*
H12B	1.3004	−0.0274	0.7552	0.181*
H12C	1.3193	0.0518	0.7026	0.181*
C13	0.7284 (4)	0.12241 (19)	0.86014 (11)	0.0422 (6)
H13	0.5887	0.1212	0.8450	0.051*
C14	0.7982 (4)	0.21236 (17)	0.89527 (10)	0.0384 (5)
C15	1.0081 (4)	0.21757 (17)	0.91771 (10)	0.0422 (5)
C16	1.0655 (4)	0.3034 (2)	0.95214 (12)	0.0512 (6)
H16	1.2027	0.3063	0.9688	0.061*
C17	0.9235 (4)	0.38342 (19)	0.96183 (12)	0.0524 (7)
H17	0.9646	0.4406	0.9846	0.063*
C18	0.7203 (5)	0.37927 (19)	0.93793 (12)	0.0503 (6)
C19	0.6555 (4)	0.29447 (18)	0.90542 (11)	0.0451 (6)
H19	0.5161	0.2919	0.8902	0.054*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Br1	0.0866 (2)	0.04417 (15)	0.1083 (3)	0.00809 (16)	−0.00202 (19)	−0.02501 (15)
O1	0.0492 (10)	0.0627 (12)	0.0659 (13)	0.0044 (9)	−0.0119 (9)	−0.0171 (10)
N1	0.0484 (12)	0.0408 (10)	0.0425 (12)	0.0010 (9)	−0.0039 (10)	−0.0101 (9)
C1	0.0501 (14)	0.0390 (12)	0.0471 (15)	0.0059 (10)	−0.0079 (12)	−0.0103 (11)
C2	0.0687 (19)	0.0389 (13)	0.0662 (19)	−0.0029 (13)	−0.0054 (16)	−0.0082 (13)
C3	0.098 (3)	0.0426 (15)	0.083 (2)	−0.0111 (16)	−0.005 (2)	−0.0158 (16)
C4	0.107 (3)	0.0502 (17)	0.087 (3)	−0.0003 (18)	−0.020 (2)	−0.0313 (17)
C5	0.094 (3)	0.069 (2)	0.058 (2)	0.0120 (19)	−0.0027 (19)	−0.0291 (17)
C6	0.0587 (16)	0.0519 (14)	0.0520 (17)	0.0123 (13)	−0.0015 (14)	−0.0127 (13)
C7	0.108 (3)	0.0476 (15)	0.067 (2)	−0.0152 (18)	0.014 (2)	−0.0056 (15)
C8	0.107 (3)	0.197 (6)	0.078 (3)	−0.001 (4)	−0.007 (3)	0.025 (3)
C9	0.091 (3)	0.148 (5)	0.123 (4)	0.008 (3)	0.032 (3)	0.000 (3)
C10	0.0646 (18)	0.0675 (16)	0.0575 (16)	0.0092 (15)	0.0088 (15)	−0.0125 (13)
C11	0.099 (6)	0.106 (6)	0.085 (6)	0.019 (5)	0.003 (5)	0.024 (5)
C11A	0.070 (8)	0.087 (11)	0.114 (18)	0.003 (7)	0.011 (8)	0.043 (12)
C12	0.084 (2)	0.109 (3)	0.170 (5)	0.012 (3)	0.032 (3)	0.001 (4)
C13	0.0442 (14)	0.0415 (12)	0.0408 (15)	−0.0048 (11)	−0.0065 (11)	−0.0051 (11)
C14	0.0465 (13)	0.0362 (11)	0.0326 (12)	−0.0048 (10)	0.0028 (10)	−0.0024 (10)
C15	0.0466 (14)	0.0435 (11)	0.0364 (12)	−0.0054 (12)	−0.0005 (12)	−0.0017 (9)
C16	0.0529 (14)	0.0573 (14)	0.0435 (14)	−0.0130 (11)	−0.0068 (13)	−0.0046 (12)
C17	0.0686 (18)	0.0429 (12)	0.0458 (15)	−0.0169 (12)	−0.0014 (13)	−0.0108 (11)
C18	0.0628 (16)	0.0340 (11)	0.0541 (17)	−0.0041 (11)	0.0033 (13)	−0.0071 (11)
C19	0.0499 (14)	0.0396 (12)	0.0457 (14)	−0.0035 (11)	−0.0014 (12)	−0.0061 (11)

Geometric parameters (Å, º) top

Br1—C18	1.897 (3)	C10—C11A	1.438 (13)
O1—C15	1.334 (3)	C10—C12	1.502 (5)
O1—H1	0.8200	C10—C11	1.569 (9)
N1—C13	1.262 (3)	C10—H10A	0.9800
N1—C1	1.422 (3)	C10—H10B	0.9800
C1—C2	1.394 (4)	C11—H11A	0.9600
C1—C6	1.401 (4)	C11—H11B	0.9600
C2—C3	1.381 (4)	C11—H11C	0.9600
C2—C7	1.517 (5)	C11A—H11D	0.9600
C3—C4	1.388 (5)	C11A—H11E	0.9600
C3—H3	0.9300	C11A—H11F	0.9600
C4—C5	1.340 (5)	C12—H12A	0.9600
C4—H4	0.9300	C12—H12B	0.9600
C5—C6	1.393 (4)	C12—H12C	0.9600
C5—H5	0.9300	C13—C14	1.462 (3)
C6—C10	1.508 (4)	C13—H13	0.9300
C7—C9	1.492 (6)	C14—C19	1.389 (3)
C7—C8	1.502 (6)	C14—C15	1.396 (4)
C7—H7	0.9800	C15—C16	1.392 (3)
C8—H8A	0.9600	C16—C17	1.364 (4)
C8—H8B	0.9600	C16—H16	0.9300
C8—H8C	0.9600	C17—C18	1.370 (4)
C9—H9A	0.9600	C17—H17	0.9300
C9—H9B	0.9600	C18—C19	1.370 (3)
C9—H9C	0.9600	C19—H19	0.9300

C15—O1—H1	109.5	C12—C10—H10A	109.9
C13—N1—C1	121.1 (2)	C6—C10—H10A	109.9
C2—C1—C6	122.2 (3)	C11—C10—H10A	109.9
C2—C1—N1	120.6 (2)	C11A—C10—H10B	99.1
C6—C1—N1	117.1 (2)	C12—C10—H10B	99.0
C3—C2—C1	117.3 (3)	C6—C10—H10B	99.0
C3—C2—C7	120.4 (3)	C10—C11—H11A	109.5
C1—C2—C7	122.3 (2)	C10—C11—H11B	109.5
C2—C3—C4	120.9 (3)	C10—C11—H11C	109.5
C2—C3—H3	119.5	C10—C11A—H11D	109.5
C4—C3—H3	119.5	C10—C11A—H11E	109.5
C5—C4—C3	121.0 (3)	H11D—C11A—H11E	109.5
C5—C4—H4	119.5	C10—C11A—H11F	109.5
C3—C4—H4	119.5	H11D—C11A—H11F	109.5
C4—C5—C6	121.0 (3)	H11E—C11A—H11F	109.5
C4—C5—H5	119.5	C10—C12—H12A	109.5
C6—C5—H5	119.5	C10—C12—H12B	109.5
C5—C6—C1	117.6 (3)	H12A—C12—H12B	109.5
C5—C6—C10	120.8 (3)	C10—C12—H12C	109.5
C1—C6—C10	121.6 (2)	H12A—C12—H12C	109.5
C9—C7—C8	110.3 (4)	H12B—C12—H12C	109.5
C9—C7—C2	113.6 (3)	N1—C13—C14	121.5 (2)
C8—C7—C2	110.6 (3)	N1—C13—H13	119.2
C9—C7—H7	107.3	C14—C13—H13	119.2
C8—C7—H7	107.3	C19—C14—C15	119.6 (2)
C2—C7—H7	107.3	C19—C14—C13	119.7 (2)
C7—C8—H8A	109.5	C15—C14—C13	120.7 (2)
C7—C8—H8B	109.5	O1—C15—C16	118.7 (2)
H8A—C8—H8B	109.5	O1—C15—C14	122.7 (2)
C7—C8—H8C	109.5	C16—C15—C14	118.6 (2)
H8A—C8—H8C	109.5	C17—C16—C15	121.0 (2)
H8B—C8—H8C	109.5	C17—C16—H16	119.5
C7—C9—H9A	109.5	C15—C16—H16	119.5
C7—C9—H9B	109.5	C16—C17—C18	119.8 (2)
H9A—C9—H9B	109.5	C16—C17—H17	120.1
C7—C9—H9C	109.5	C18—C17—H17	120.1
H9A—C9—H9C	109.5	C19—C18—C17	120.8 (2)
H9B—C9—H9C	109.5	C19—C18—Br1	119.9 (2)
C11A—C10—C12	130.0 (11)	C17—C18—Br1	119.25 (19)
C11A—C10—C6	110.4 (6)	C18—C19—C14	120.0 (3)
C12—C10—C6	112.1 (3)	C18—C19—H19	120.0
C12—C10—C11	102.2 (7)	C14—C19—H19	120.0
C6—C10—C11	112.6 (4)

C13—N1—C1—C2	−78.3 (3)	C1—C6—C10—C11A	−91.3 (18)
C13—N1—C1—C6	105.7 (3)	C5—C6—C10—C12	−65.0 (4)
C6—C1—C2—C3	0.3 (4)	C1—C6—C10—C12	115.6 (4)
N1—C1—C2—C3	−175.6 (3)	C5—C6—C10—C11	49.7 (8)
C6—C1—C2—C7	178.4 (3)	C1—C6—C10—C11	−129.7 (8)
N1—C1—C2—C7	2.6 (4)	C1—N1—C13—C14	−179.5 (2)
C1—C2—C3—C4	−0.5 (5)	N1—C13—C14—C19	179.9 (2)
C7—C2—C3—C4	−178.7 (3)	N1—C13—C14—C15	1.2 (4)
C2—C3—C4—C5	−0.6 (6)	C19—C14—C15—O1	−177.2 (2)
C3—C4—C5—C6	2.1 (6)	C13—C14—C15—O1	1.5 (4)
C4—C5—C6—C1	−2.2 (5)	C19—C14—C15—C16	2.9 (3)
C4—C5—C6—C10	178.3 (3)	C13—C14—C15—C16	−178.4 (2)
C2—C1—C6—C5	1.1 (4)	O1—C15—C16—C17	177.2 (2)
N1—C1—C6—C5	177.1 (3)	C14—C15—C16—C17	−2.8 (4)
C2—C1—C6—C10	−179.5 (3)	C15—C16—C17—C18	0.6 (4)
N1—C1—C6—C10	−3.5 (4)	C16—C17—C18—C19	1.5 (4)
C3—C2—C7—C9	−46.7 (5)	C16—C17—C18—Br1	−178.9 (2)
C1—C2—C7—C9	135.2 (4)	C17—C18—C19—C14	−1.4 (4)
C3—C2—C7—C8	78.0 (4)	Br1—C18—C19—C14	178.98 (19)
C1—C2—C7—C8	−100.1 (4)	C15—C14—C19—C18	−0.8 (4)
C5—C6—C10—C11A	88.1 (18)	C13—C14—C19—C18	−179.5 (2)

Hydrogen-bond geometry (Å, º) top

Cg2 is the centroid of the C14–C19 ring.

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N1	0.82	1.87	2.597 (3)	147
C16—H16···Cg2ⁱ	0.93	2.86	3.522 (3)	129

Symmetry code: (i) −x, y+1/2, −z+5/2.

Experimental details

Crystal data
Chemical formula	C₁₉H₂₂BrNO
M_r	360.29
Crystal system, space group	Orthorhombic, P2₁2₁2₁
Temperature (K)	295
a, b, c (Å)	6.1851 (12), 12.759 (3), 22.698 (5)
V (Å³)	1791.3 (6)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	2.30
Crystal size (mm)	0.24 × 0.22 × 0.18

Data collection
Diffractometer	Bruker Kappa APEXII diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.609, 0.683
No. of measured, independent and observed [I > 2σ(I)] reflections	23590, 5107, 3242
R_int	0.039
(sin θ/λ)_max (Å⁻¹)	0.699

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.040, 0.100, 1.01
No. of reflections	5107
No. of parameters	214
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.38, −0.22
Absolute structure	Flack (1983), 2179 Friedel pairs
Absolute structure parameter	0.011 (10)

Computer programs: APEX2 (Bruker, 2004), SAINT (Bruker, 2004), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

Cg2 is the centroid of the C14–C19 ring.

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N1	0.82	1.87	2.597 (3)	147
C16—H16···Cg2ⁱ	0.93	2.86	3.522 (3)	129

Symmetry code: (i) −x, y+1/2, −z+5/2.

Acknowledgements

The authors wish to acknowledge the SAIF, IIT Madras, for the data collection.

References

Bruker (2004). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
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Volume 68| Part 6| June 2012| Page o1782

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