5-Meth­oxy-2-{[4-(morpholin-4-yl)phen­yl]imino­meth­yl}phenol

Dhahagani, K.; Manvizhi, K.; Chakkaravarthi, G.; Anbalagan, G.; Rajagopal, G.

doi:10.1107/S1600536811034659

organic compounds

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ISSN: 2056-9890

Volume 67| Part 9| September 2011| Page o2501

doi:10.1107/S1600536811034659

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5-Methoxy-2-{[4-(morpholin-4-yl)phenyl]iminomethyl}phenol

K. Dhahagani,^a K. Manvizhi,^b G. Chakkaravarthi,^c ^* G. Anbalagan ^d and G. Rajagopal ^a

^aDepartment of Chemistry, Government Arts College, Melur 625 106, India, ^bDepartment of Chemistry, Anand Institute of Higher Technology, Kazhipattur, Chennai 603 103, India, ^cDepartment of Physics, CPCL Polytechnic College, Chennai 600 068, India, and ^dDepartment of Physics, Presidency College (Autonomous), Chennai 600 005, India
^*Correspondence e-mail: chakkaravarthi_2005@yahoo.com, rajagopal18@yahoo.com

(Received 22 August 2011; accepted 23 August 2011; online 27 August 2011)

In the title compound, C₁₈H₂₀N₂O₃, the dihedral angle between the two aromatic rings is 33.66 (6)°. The morpholine ring adopts a chair conformation. The molecular structure is stabilized by an intramolecular O—H⋯N hydrogen bond. In the crystal, molecules are linked via weak intermolecular C—H⋯O and C—H⋯π interactions.

Related literature

For the biological activity of morpholine derivatives, see: Lan et al. (2010 ); Raparti et al. (2009 ). For standard bond lengths, see: Allen et al. (1987 ). For a related structure, see: Yang et al. (2011 ). For the definition of puckering parameters, see: Cremer & Pople (1975 ). For graph-set notation, see: Etter et al. (1990 ).

Experimental

Crystal data

C₁₈H₂₀N₂O₃
M_r = 312.36
Monoclinic, P 2₁ /n
a = 10.623 (6) Å
b = 9.106 (5) Å
c = 16.640 (5) Å
β = 97.446 (6)°
V = 1596.2 (13) Å³
Z = 4
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 295 K
0.28 × 0.24 × 0.20 mm

Data collection

Bruker Kappa APEXII diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.975, T_max = 0.982
21296 measured reflections
4941 independent reflections
2761 reflections with I > 2σ(I)
R_int = 0.031
Standard reflections: 0

Refinement

R[F² > 2σ(F²)] = 0.066
wR(F²) = 0.204
S = 1.05
4941 reflections
210 parameters
H-atom parameters constrained
Δρ_max = 0.29 e Å⁻³
Δρ_min = −0.27 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

Cg2 and Cg3 are the centroids of the C5–C10 and C12–C17 rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H2⋯N2	0.82	1.87	2.600 (2)	148
C14—H14⋯O3ⁱ	0.93	2.53	3.412 (3)	158
C18—H18B⋯O1ⁱⁱ	0.96	2.44	3.289 (3)	148
C2—H2A⋯Cg3ⁱⁱⁱ	0.97	2.92	3.799 (4)	152
C16—H16⋯Cg2^iv	0.93	2.86	3.663 (3)	146
Symmetry codes: (i) -x+3, -y+1, -z+1; (ii) $[x+{\script{3\over 2}}, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]$ ; (iii) x-1, y, z; (iv) $[-x+{\script{5\over 2}}, y-{\script{1\over 2}}, -z+{\script{3\over 2}}]$ .

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/S1600536811034659/bt5628sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811034659/bt5628Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536811034659/bt5628Isup3.cml

checkCIF report

Comment top

Morpholine derivatives possess anticancer and antimicrobial (Lan et al., 2010; Raparti et al., 2009) activities. The goemetric parameters of the title compound (I) are comparable with the literature values and reported related structure (Allen et al., 1987; Yang et al., 2011).

The mean planes of the two benzene rings (C5-C10) and (C12-C17) are oriented at an angle of 33.66 (6)°. The morpholine ring adopts chair conformation [Puckering parameters are Q = 0.470 (3)Å, θ = 7.0 (2)° and Φ = 11 (3)° (Cremer & Pople, 1975) for the ring (O1/C1/C2/N1/C3/C4)].

The molecular structure is stabilized by weak intramolecular O—H···N hydrogen bonding. In the crystal structure, the molecules are linked via weak intermolecular C—H···O and C—H···π (Fig. 2 and Table 1) interactions. Intramolecular O2-H2···N2 hydrogen bonding generates a six-membered ring, with S(6) graph-set motif and the intermolecular C13-H13···O3 interaction generates an eight-membered ring, with R₂²(8) graph-set motif.

Related literature top

For the biological activity of morpholine derivatives, see: Lan et al. (2010); Raparti et al. (2009). For standard bond lengths, see: Allen et al. (1987). For a related structure, see: Yang et al.(2011). For the definition of puckering parameters, see: Cremer & Pople (1975). For graph-set notation, see: Etter et al. (1990).

Experimental top

An ethanolic solution (20 ml) of 4-(4-aminophenyl)morpholine (10 mmol) was magnetically stirred in a round bottom flask followed by drop wise addition of ethanolic solution of 4-methoxysalicylaldehyde (10 mmol). The reaction mixture was then refluxed for two hours and upon cooling to 273 K, a pale yellow crystalline solid precipitates from the mixture. The solid which is separated out was filtered washed with ice cold ethanol and dried in vaccuo over anhydrous CaCl₂. Single crystals suitable for the X-ray diffraction were obtained by slow evaporation of a solution of the title compound in methanol at room temperature. Melting Point: 457 K.

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 (I), with atom labels and 30% probability displacement ellipsoids for non-H atoms.
	Fig. 2. The packing of (I), viewed down a axis. Intermolecular Hydrogen bonds are shown as dashed lines. H atoms not involved in hydrogen bonding have been omitted.

5-Methoxy-2-{[4-(morpholin-4-yl)phenyl]iminomethyl}phenol top

Crystal data top

C₁₈H₂₀N₂O₃	F(000) = 664
M_r = 312.36	D_x = 1.300 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 4380 reflections
a = 10.623 (6) Å	θ = 2.5–30.6°
b = 9.106 (5) Å	µ = 0.09 mm⁻¹
c = 16.640 (5) Å	T = 295 K
β = 97.446 (6)°	Block, colourless
V = 1596.2 (13) Å³	0.28 × 0.24 × 0.20 mm
Z = 4

Data collection top

Bruker Kappa APEXII diffractometer	4941 independent reflections
Radiation source: fine-focus sealed tube	2761 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.031
ω and ϕ scans	θ_max = 30.7°, θ_min = 2.2°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −9→15
T_min = 0.975, T_max = 0.982	k = −12→12
21296 measured reflections	l = −23→23

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)] = 0.066	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.204	H-atom parameters constrained
S = 1.05	w = 1/[σ²(F_o²) + (0.089P)² + 0.3452P] where P = (F_o² + 2F_c²)/3
4941 reflections	(Δ/σ)_max < 0.001
210 parameters	Δρ_max = 0.29 e Å⁻³
0 restraints	Δρ_min = −0.27 e Å⁻³

Crystal data top

C₁₈H₂₀N₂O₃	V = 1596.2 (13) Å³
M_r = 312.36	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 10.623 (6) Å	µ = 0.09 mm⁻¹
b = 9.106 (5) Å	T = 295 K
c = 16.640 (5) Å	0.28 × 0.24 × 0.20 mm
β = 97.446 (6)°

Data collection top

Bruker Kappa APEXII diffractometer	4941 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	2761 reflections with I > 2σ(I)
T_min = 0.975, T_max = 0.982	R_int = 0.031
21296 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.066	0 restraints
wR(F²) = 0.204	H-atom parameters constrained
S = 1.05	Δρ_max = 0.29 e Å⁻³
4941 reflections	Δρ_min = −0.27 e Å⁻³
210 parameters

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

	x	y	z	U_iso*/U_eq
C1	0.4258 (2)	0.3507 (4)	0.86902 (17)	0.0858 (8)
H1A	0.3592	0.4221	0.8539	0.103*
H1B	0.3974	0.2575	0.8448	0.103*
C2	0.5421 (2)	0.3978 (3)	0.83441 (17)	0.0756 (7)
H2A	0.5265	0.3921	0.7758	0.091*
H2B	0.5609	0.4993	0.8491	0.091*
C3	0.6624 (2)	0.2790 (4)	0.94823 (13)	0.0993 (11)
H3A	0.6977	0.3649	0.9774	0.119*
H3B	0.7214	0.1985	0.9605	0.119*
C4	0.5395 (2)	0.2410 (4)	0.97652 (15)	0.1022 (11)
H4A	0.5149	0.1435	0.9570	0.123*
H4B	0.5519	0.2374	1.0353	0.123*
C5	0.75890 (16)	0.31894 (19)	0.82520 (9)	0.0409 (4)
C6	0.76084 (19)	0.3993 (2)	0.75393 (12)	0.0559 (5)
H6	0.6885	0.4501	0.7320	0.067*
C7	0.86803 (19)	0.4047 (2)	0.71547 (11)	0.0549 (5)
H7	0.8667	0.4599	0.6683	0.066*
C8	0.97710 (16)	0.33047 (18)	0.74518 (9)	0.0396 (4)
C9	0.97771 (17)	0.2539 (2)	0.81688 (10)	0.0472 (4)
H9	1.0510	0.2051	0.8390	0.057*
C10	0.87091 (18)	0.2490 (2)	0.85609 (10)	0.0482 (4)
H10	0.8741	0.1974	0.9045	0.058*
C11	1.16925 (16)	0.24530 (19)	0.70644 (10)	0.0421 (4)
H11	1.1595	0.1603	0.7360	0.051*
C12	1.28060 (16)	0.26119 (18)	0.66578 (9)	0.0393 (4)
C13	1.30539 (17)	0.39126 (18)	0.62486 (10)	0.0402 (4)
C14	1.41223 (17)	0.40335 (19)	0.58674 (10)	0.0450 (4)
H14	1.4284	0.4902	0.5605	0.054*
C15	1.49540 (17)	0.2874 (2)	0.58729 (10)	0.0461 (4)
C16	1.47404 (19)	0.1582 (2)	0.62718 (13)	0.0559 (5)
H16	1.5307	0.0802	0.6280	0.067*
C17	1.36751 (19)	0.1477 (2)	0.66548 (12)	0.0532 (5)
H17	1.3530	0.0609	0.6923	0.064*
C18	1.6838 (2)	0.1948 (3)	0.54114 (18)	0.0868 (8)
H18A	1.7226	0.1680	0.5944	0.130*
H18B	1.7482	0.2261	0.5094	0.130*
H18C	1.6397	0.1117	0.5157	0.130*
N1	0.64900 (14)	0.30818 (19)	0.86311 (8)	0.0491 (4)
N2	1.08397 (14)	0.34434 (16)	0.70305 (8)	0.0420 (3)
O1	0.44192 (16)	0.3353 (2)	0.95242 (11)	0.0846 (6)
O2	1.22521 (14)	0.50605 (14)	0.62211 (9)	0.0607 (4)
H2	1.1635	0.4839	0.6445	0.091*
O3	1.59655 (14)	0.31149 (17)	0.54691 (9)	0.0650 (4)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0467 (13)	0.118 (2)	0.0978 (19)	0.0095 (14)	0.0282 (13)	0.0384 (16)
C2	0.0460 (12)	0.0875 (17)	0.0984 (18)	0.0089 (12)	0.0296 (12)	0.0292 (14)
C3	0.0464 (13)	0.211 (4)	0.0423 (11)	−0.0168 (18)	0.0123 (9)	0.0158 (15)
C4	0.0513 (14)	0.204 (4)	0.0542 (13)	0.0027 (19)	0.0187 (11)	0.0345 (17)
C5	0.0358 (9)	0.0504 (10)	0.0378 (8)	−0.0008 (7)	0.0096 (7)	0.0001 (7)
C6	0.0391 (10)	0.0789 (14)	0.0515 (10)	0.0145 (9)	0.0124 (8)	0.0206 (9)
C7	0.0457 (11)	0.0742 (13)	0.0474 (9)	0.0086 (9)	0.0165 (8)	0.0204 (9)
C8	0.0379 (9)	0.0430 (9)	0.0400 (8)	−0.0018 (7)	0.0131 (7)	−0.0021 (6)
C9	0.0398 (9)	0.0576 (11)	0.0457 (9)	0.0105 (8)	0.0118 (7)	0.0082 (8)
C10	0.0458 (10)	0.0589 (11)	0.0422 (8)	0.0064 (9)	0.0142 (8)	0.0119 (8)
C11	0.0431 (10)	0.0409 (9)	0.0443 (8)	−0.0020 (8)	0.0131 (7)	0.0012 (7)
C12	0.0381 (9)	0.0408 (9)	0.0407 (8)	0.0013 (7)	0.0119 (7)	0.0012 (6)
C13	0.0420 (10)	0.0385 (8)	0.0415 (8)	0.0030 (7)	0.0112 (7)	−0.0010 (6)
C14	0.0479 (11)	0.0416 (9)	0.0483 (9)	−0.0017 (8)	0.0169 (8)	0.0034 (7)
C15	0.0383 (9)	0.0576 (11)	0.0454 (9)	0.0020 (8)	0.0161 (7)	0.0031 (8)
C16	0.0473 (11)	0.0549 (11)	0.0693 (12)	0.0179 (9)	0.0218 (9)	0.0137 (9)
C17	0.0519 (11)	0.0478 (10)	0.0640 (11)	0.0099 (9)	0.0228 (9)	0.0160 (8)
C18	0.0587 (15)	0.106 (2)	0.105 (2)	0.0246 (14)	0.0441 (14)	0.0078 (16)
N1	0.0366 (8)	0.0714 (11)	0.0413 (7)	0.0044 (7)	0.0120 (6)	0.0086 (7)
N2	0.0387 (8)	0.0472 (8)	0.0425 (7)	0.0013 (6)	0.0141 (6)	−0.0004 (6)
O1	0.0549 (10)	0.1205 (15)	0.0859 (12)	−0.0139 (10)	0.0373 (9)	−0.0139 (10)
O2	0.0624 (9)	0.0448 (7)	0.0820 (10)	0.0152 (7)	0.0362 (8)	0.0122 (6)
O3	0.0515 (8)	0.0765 (10)	0.0743 (9)	0.0092 (7)	0.0351 (7)	0.0138 (7)

Geometric parameters (Å, º) top

C1—O1	1.383 (3)	C9—C10	1.381 (2)
C1—C2	1.492 (3)	C9—H9	0.9300
C1—H1A	0.9700	C10—H10	0.9300
C1—H1B	0.9700	C11—N2	1.274 (2)
C2—N1	1.430 (3)	C11—C12	1.444 (2)
C2—H2A	0.9700	C11—H11	0.9300
C2—H2B	0.9700	C12—C17	1.386 (2)
C3—N1	1.430 (3)	C12—C13	1.408 (2)
C3—C4	1.485 (3)	C13—O2	1.345 (2)
C3—H3A	0.9700	C13—C14	1.374 (2)
C3—H3B	0.9700	C14—C15	1.376 (3)
C4—O1	1.365 (3)	C14—H14	0.9300
C4—H4A	0.9700	C15—O3	1.357 (2)
C4—H4B	0.9700	C15—C16	1.384 (3)
C5—C10	1.388 (2)	C16—C17	1.372 (3)
C5—C6	1.396 (2)	C16—H16	0.9300
C5—N1	1.400 (2)	C17—H17	0.9300
C6—C7	1.378 (3)	C18—O3	1.421 (3)
C6—H6	0.9300	C18—H18A	0.9600
C7—C8	1.377 (3)	C18—H18B	0.9600
C7—H7	0.9300	C18—H18C	0.9600
C8—C9	1.381 (2)	O2—H2	0.8200
C8—N2	1.415 (2)

O1—C1—C2	114.5 (2)	C8—C9—H9	119.6
O1—C1—H1A	108.6	C9—C10—C5	121.83 (16)
C2—C1—H1A	108.6	C9—C10—H10	119.1
O1—C1—H1B	108.6	C5—C10—H10	119.1
C2—C1—H1B	108.6	N2—C11—C12	121.94 (16)
H1A—C1—H1B	107.6	N2—C11—H11	119.0
N1—C2—C1	111.6 (2)	C12—C11—H11	119.0
N1—C2—H2A	109.3	C17—C12—C13	117.33 (16)
C1—C2—H2A	109.3	C17—C12—C11	120.88 (16)
N1—C2—H2B	109.3	C13—C12—C11	121.79 (15)
C1—C2—H2B	109.3	O2—C13—C14	118.62 (15)
H2A—C2—H2B	108.0	O2—C13—C12	120.85 (16)
N1—C3—C4	112.25 (18)	C14—C13—C12	120.53 (15)
N1—C3—H3A	109.2	C13—C14—C15	120.22 (16)
C4—C3—H3A	109.2	C13—C14—H14	119.9
N1—C3—H3B	109.2	C15—C14—H14	119.9
C4—C3—H3B	109.2	O3—C15—C14	114.92 (16)
H3A—C3—H3B	107.9	O3—C15—C16	124.38 (17)
O1—C4—C3	115.2 (3)	C14—C15—C16	120.70 (17)
O1—C4—H4A	108.5	C17—C16—C15	118.59 (17)
C3—C4—H4A	108.5	C17—C16—H16	120.7
O1—C4—H4B	108.5	C15—C16—H16	120.7
C3—C4—H4B	108.5	C16—C17—C12	122.63 (17)
H4A—C4—H4B	107.5	C16—C17—H17	118.7
C10—C5—C6	116.66 (16)	C12—C17—H17	118.7
C10—C5—N1	121.72 (15)	O3—C18—H18A	109.5
C6—C5—N1	121.62 (16)	O3—C18—H18B	109.5
C7—C6—C5	121.18 (17)	H18A—C18—H18B	109.5
C7—C6—H6	119.4	O3—C18—H18C	109.5
C5—C6—H6	119.4	H18A—C18—H18C	109.5
C8—C7—C6	121.55 (17)	H18B—C18—H18C	109.5
C8—C7—H7	119.2	C5—N1—C2	118.82 (16)
C6—C7—H7	119.2	C5—N1—C3	118.53 (16)
C7—C8—C9	117.88 (16)	C2—N1—C3	114.18 (19)
C7—C8—N2	118.04 (15)	C11—N2—C8	121.75 (15)
C9—C8—N2	123.97 (16)	C4—O1—C1	110.42 (19)
C10—C9—C8	120.83 (16)	C13—O2—H2	109.5
C10—C9—H9	119.6	C15—O3—C18	118.55 (17)

O1—C1—C2—N1	50.7 (3)	C13—C14—C15—C16	−1.1 (3)
N1—C3—C4—O1	−49.6 (4)	O3—C15—C16—C17	−179.70 (19)
C10—C5—C6—C7	1.8 (3)	C14—C15—C16—C17	0.6 (3)
N1—C5—C6—C7	−177.56 (19)	C15—C16—C17—C12	0.0 (3)
C5—C6—C7—C8	0.5 (3)	C13—C12—C17—C16	−0.2 (3)
C6—C7—C8—C9	−2.3 (3)	C11—C12—C17—C16	179.64 (19)
C6—C7—C8—N2	−178.64 (18)	C10—C5—N1—C2	171.9 (2)
C7—C8—C9—C10	1.8 (3)	C6—C5—N1—C2	−8.8 (3)
N2—C8—C9—C10	177.85 (17)	C10—C5—N1—C3	25.7 (3)
C8—C9—C10—C5	0.6 (3)	C6—C5—N1—C3	−155.0 (2)
C6—C5—C10—C9	−2.3 (3)	C1—C2—N1—C5	167.9 (2)
N1—C5—C10—C9	177.01 (17)	C1—C2—N1—C3	−44.4 (3)
N2—C11—C12—C17	−175.33 (17)	C4—C3—N1—C5	−168.5 (3)
N2—C11—C12—C13	4.5 (3)	C4—C3—N1—C2	43.8 (4)
C17—C12—C13—O2	179.68 (17)	C12—C11—N2—C8	−177.88 (15)
C11—C12—C13—O2	−0.2 (3)	C7—C8—N2—C11	−154.33 (18)
C17—C12—C13—C14	−0.2 (3)	C9—C8—N2—C11	29.6 (3)
C11—C12—C13—C14	179.93 (16)	C3—C4—O1—C1	54.7 (4)
O2—C13—C14—C15	−179.05 (17)	C2—C1—O1—C4	−55.3 (3)
C12—C13—C14—C15	0.9 (3)	C14—C15—O3—C18	−177.0 (2)
C13—C14—C15—O3	179.24 (16)	C16—C15—O3—C18	3.3 (3)

Hydrogen-bond geometry (Å, º) top

Cg2 and Cg3 are the centroids of the C5–C10 and C12–C17 rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2···N2	0.82	1.87	2.600 (2)	148
C14—H14···O3ⁱ	0.93	2.53	3.412 (3)	158
C18—H18B···O1ⁱⁱ	0.96	2.44	3.289 (3)	148
C2—H2A···Cg3ⁱⁱⁱ	0.97	2.92	3.799 (4)	152
C16—H16···Cg2^iv	0.93	2.86	3.663 (3)	146

Symmetry codes: (i) −x+3, −y+1, −z+1; (ii) x+3/2, −y+1/2, z−1/2; (iii) x−1, y, z; (iv) −x+5/2, y−1/2, −z+3/2.

Experimental details

Crystal data
Chemical formula	C₁₈H₂₀N₂O₃
M_r	312.36
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	295
a, b, c (Å)	10.623 (6), 9.106 (5), 16.640 (5)
β (°)	97.446 (6)
V (Å³)	1596.2 (13)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.28 × 0.24 × 0.20

Data collection
Diffractometer	Bruker Kappa APEXII diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.975, 0.982
No. of measured, independent and observed [I > 2σ(I)] reflections	21296, 4941, 2761
R_int	0.031
(sin θ/λ)_max (Å⁻¹)	0.719

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.066, 0.204, 1.05
No. of reflections	4941
No. of parameters	210
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.29, −0.27

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

Hydrogen-bond geometry (Å, º) top

Cg2 and Cg3 are the centroids of the C5–C10 and C12–C17 rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2···N2	0.82	1.87	2.600 (2)	148
C14—H14···O3ⁱ	0.93	2.53	3.412 (3)	158
C18—H18B···O1ⁱⁱ	0.96	2.44	3.289 (3)	148
C2—H2A···Cg3ⁱⁱⁱ	0.97	2.92	3.799 (4)	152
C16—H16···Cg2^iv	0.93	2.86	3.663 (3)	146

Symmetry codes: (i) −x+3, −y+1, −z+1; (ii) x+3/2, −y+1/2, z−1/2; (iii) x−1, y, z; (iv) −x+5/2, y−1/2, −z+3/2.

Acknowledgements

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

References

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