Benzil bis­(ketazine)

Patra, G.K.; Mukherjee, A.; Ng, S.W.

doi:10.1107/S1600536809024489

organic compounds

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ISSN: 2056-9890

Volume 65| Part 8| August 2009| Page o1745

doi:10.1107/S1600536809024489

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Benzil bis(ketazine)

Goutam Kumar Patra,^a Anindita Mukherjee ^a and Seik Weng Ng ^b ^*

^aDepartment of Chemistry, Vijaygarh Jyotish Ray College, 8/2 Vijaygarh, Jadavpur, Kolkata 32, India, and ^bDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
^*Correspondence e-mail: seikweng@um.edu.my

(Received 24 June 2009; accepted 25 June 2009; online 4 July 2009)

The title compound (systematic name: 1,1′,2,2′-tetraphenyl-2,2′-azinodiethanone), C₂₈H₂₀N₂O₂, was obtained by the reaction of benzil monohydrazone with chromium(III) nitrate. The dibenzylidene hydrazine unit is nearly planar (r.m.s. deviation = 0.073 Å) and the two benzoyl units are oriented almost perpendicular to it [dihedral angle = 87.81 (2), 87.81 (2)°]. The molecules are linked into chains along the c axis by C—H⋯O hydrogen bonds and the chains are cross-linked via C—H⋯π interactions involving the benzoyl phenyl rings.

Related literature

For the synthesis of title compound using copper bis(acetylacetonate) as catalyst, see: Ibata & Singh (1994 ); Singh (1983 ).

Experimental

Crystal data

C₂₈H₂₀N₂O₂
M_r = 416.46
Monoclinic, P 2₁ /c
a = 8.2875 (2) Å
b = 22.1023 (4) Å
c = 11.6602 (2) Å
β = 97.539 (1)°
V = 2117.37 (7) Å³
Z = 4
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 140 K
0.30 × 0.04 × 0.03 mm

Data collection

Bruker SMART APEX area-detector diffractometer
Absorption correction: none
17323 measured reflections
4857 independent reflections
3510 reflections with I > 2σ(I)
R_int = 0.030

Refinement

R[F² > 2σ(F²)] = 0.040
wR(F²) = 0.107
S = 1.03
4857 reflections
289 parameters
H-atom parameters constrained
Δρ_max = 0.24 e Å⁻³
Δρ_min = −0.21 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C1—H1⋯O1ⁱ	0.95	2.24	3.0832 (16)	147
C13—H13⋯Cg1ⁱⁱ	0.95	2.68	3.5705 (16)	157
C18—H18⋯Cg2ⁱⁱⁱ	0.95	2.66	3.5304 (16)	153
Symmetry codes: (i) $[x, -y+{\script{3\over 2}}, z+{\script{1\over 2}}]$ ; (ii) x+1, y, z; (iii) x-1, y, z. Cg1 and Cg2 are centroids of the C1–C6 and C23–C28 rings, respectively.

Data collection: APEX2 (Bruker, 2008 ); cell refinement: SAINT (Bruker, 2008); 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/S1600536809024489/ci2835sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809024489/ci2835Isup2.hkl

checkCIF report

Related literature top

For the synthesis of title compound using copper bis(acetylacetonate) as catalyst, see: Ibata & Singh (1994); Singh (1983). Cg1 and Cg2 are centroids of the C1–C6 and C23–C28 rings, respectively

Experimental top

Benzil monohydrazone (0.224 g, 1 mmol) was dissolved in acetonitrile (20 ml) and to this was added chromium nitrate nonahyrate (0.40 g, 1 mmol). The greenish yellowish mixture was stirred at room temperature for 6 h. Bright yellow prisms were collected in 40% yield.

Computing details top

Data collection: APEX2 (Bruker, 2008); cell refinement: SAINT (Bruker, 2008); data reduction: SAINT (Bruker, 2008); 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. Displacement ellipsoid plot (Barbour, 2001) of C₂₈H₂₀N₂O₂ at the 70% probability level; H atoms are drawn as spheres of arbitrary radius.

1,1',2,2'-tetraphenyl-2,2'-azinodiethanone top

Crystal data top

C₂₈H₂₀N₂O₂	F(000) = 872
M_r = 416.46	D_x = 1.306 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 3878 reflections
a = 8.2875 (2) Å	θ = 2.5–27.9°
b = 22.1023 (4) Å	µ = 0.08 mm⁻¹
c = 11.6602 (2) Å	T = 140 K
β = 97.539 (1)°	Prism, yellow
V = 2117.37 (7) Å³	0.30 × 0.04 × 0.03 mm
Z = 4

Data collection top

Bruker SMART APEX area-detector diffractometer	3510 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.030
Graphite monochromator	θ_max = 27.5°, θ_min = 1.8°
ω scans	h = −10→10
17323 measured reflections	k = −28→27
4857 independent reflections	l = −15→15

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)] = 0.040	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.107	H-atom parameters constrained
S = 1.03	w = 1/[σ²(F_o²) + (0.0486P)² + 0.4715P] where P = (F_o² + 2F_c²)/3
4857 reflections	(Δ/σ)_max = 0.001
289 parameters	Δρ_max = 0.24 e Å⁻³
0 restraints	Δρ_min = −0.21 e Å⁻³

Crystal data top

C₂₈H₂₀N₂O₂	V = 2117.37 (7) Å³
M_r = 416.46	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 8.2875 (2) Å	µ = 0.08 mm⁻¹
b = 22.1023 (4) Å	T = 140 K
c = 11.6602 (2) Å	0.30 × 0.04 × 0.03 mm
β = 97.539 (1)°

Data collection top

Bruker SMART APEX area-detector diffractometer	3510 reflections with I > 2σ(I)
17323 measured reflections	R_int = 0.030
4857 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.040	0 restraints
wR(F²) = 0.107	H-atom parameters constrained
S = 1.03	Δρ_max = 0.24 e Å⁻³
4857 reflections	Δρ_min = −0.21 e Å⁻³
289 parameters

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

	x	y	z	U_iso*/U_eq
O1	0.37058 (13)	0.75630 (5)	0.13158 (8)	0.0366 (3)
O2	0.17265 (13)	0.56277 (5)	0.47749 (8)	0.0336 (3)
N1	0.34699 (13)	0.66169 (5)	0.33697 (11)	0.0257 (3)
N2	0.18382 (13)	0.66513 (5)	0.28286 (10)	0.0252 (3)
C1	0.27649 (16)	0.81384 (6)	0.40407 (11)	0.0215 (3)
H1	0.3294	0.7835	0.4531	0.026*
C2	0.20231 (17)	0.86230 (7)	0.45113 (13)	0.0303 (3)
H2	0.2043	0.8653	0.5326	0.036*
C3	0.12519 (19)	0.90640 (7)	0.37938 (15)	0.0377 (4)
H3	0.0744	0.9397	0.4118	0.045*
C4	0.12170 (19)	0.90223 (7)	0.26063 (15)	0.0370 (4)
H4	0.0678	0.9325	0.2119	0.044*
C5	0.19592 (17)	0.85447 (6)	0.21267 (13)	0.0278 (3)
H5	0.1945	0.8520	0.1312	0.033*
C6	0.27335 (15)	0.80970 (6)	0.28467 (11)	0.0198 (3)
C7	0.35415 (15)	0.75841 (6)	0.23347 (11)	0.0219 (3)
C8	0.42829 (16)	0.70877 (6)	0.31371 (11)	0.0211 (3)
C9	0.59933 (16)	0.71554 (6)	0.36520 (11)	0.0211 (3)
C10	0.66251 (18)	0.67959 (7)	0.45829 (13)	0.0318 (3)
H10	0.5949	0.6504	0.4881	0.038*
C11	0.82226 (18)	0.68586 (7)	0.50792 (14)	0.0349 (4)
H11	0.8639	0.6612	0.5717	0.042*
C12	0.92181 (17)	0.72815 (7)	0.46459 (13)	0.0296 (3)
H12	1.0319	0.7324	0.4985	0.036*
C13	0.86090 (17)	0.76404 (7)	0.37219 (13)	0.0312 (3)
H13	0.9294	0.7929	0.3422	0.037*
C14	0.70016 (17)	0.75823 (6)	0.32287 (12)	0.0267 (3)
H14	0.6586	0.7835	0.2599	0.032*
C15	0.10218 (16)	0.61745 (6)	0.30204 (11)	0.0215 (3)
C16	−0.06870 (16)	0.61175 (6)	0.24937 (11)	0.0215 (3)
C17	−0.16874 (17)	0.56676 (6)	0.28567 (13)	0.0279 (3)
H17	−0.1274	0.5398	0.3460	0.033*
C18	−0.32831 (18)	0.56134 (7)	0.23374 (14)	0.0327 (3)
H18	−0.3961	0.5306	0.2586	0.039*
C19	−0.38917 (17)	0.60026 (7)	0.14627 (13)	0.0307 (3)
H19	−0.4987	0.5962	0.1110	0.037*
C20	−0.29147 (17)	0.64511 (7)	0.10965 (13)	0.0302 (3)
H20	−0.3338	0.6720	0.0495	0.036*
C21	−0.13179 (17)	0.65073 (6)	0.16090 (12)	0.0269 (3)
H21	−0.0646	0.6815	0.1355	0.032*
C22	0.17830 (16)	0.56479 (6)	0.37387 (11)	0.0222 (3)
C23	0.25313 (16)	0.51611 (6)	0.31005 (12)	0.0215 (3)
C24	0.34362 (17)	0.47038 (7)	0.37097 (13)	0.0299 (3)
H24	0.3554	0.4697	0.4531	0.036*
C25	0.4161 (2)	0.42613 (7)	0.31128 (15)	0.0372 (4)
H25	0.4800	0.3956	0.3528	0.045*
C26	0.39637 (19)	0.42599 (7)	0.19180 (14)	0.0344 (4)
H26	0.4459	0.3952	0.1516	0.041*
C27	0.30485 (18)	0.47042 (7)	0.13063 (13)	0.0309 (3)
H27	0.2903	0.4700	0.0484	0.037*
C28	0.23428 (17)	0.51564 (6)	0.18982 (12)	0.0242 (3)
H28	0.1725	0.5466	0.1478	0.029*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0392 (6)	0.0513 (7)	0.0191 (5)	0.0020 (5)	0.0023 (4)	−0.0069 (5)
O2	0.0389 (6)	0.0379 (6)	0.0238 (5)	0.0007 (5)	0.0037 (4)	−0.0048 (4)
N1	0.0177 (6)	0.0207 (6)	0.0374 (7)	−0.0007 (4)	−0.0007 (5)	−0.0034 (5)
N2	0.0167 (6)	0.0214 (6)	0.0366 (7)	−0.0006 (4)	0.0000 (5)	−0.0056 (5)
C1	0.0188 (6)	0.0230 (6)	0.0220 (7)	−0.0012 (5)	−0.0003 (5)	0.0008 (5)
C2	0.0244 (7)	0.0341 (8)	0.0317 (8)	−0.0013 (6)	0.0009 (6)	−0.0103 (6)
C3	0.0286 (8)	0.0273 (8)	0.0549 (11)	0.0056 (6)	−0.0034 (7)	−0.0120 (7)
C4	0.0334 (8)	0.0229 (7)	0.0501 (10)	0.0023 (6)	−0.0119 (7)	0.0057 (7)
C5	0.0265 (7)	0.0266 (7)	0.0278 (7)	−0.0057 (6)	−0.0051 (6)	0.0066 (6)
C6	0.0162 (6)	0.0200 (6)	0.0227 (7)	−0.0044 (5)	0.0004 (5)	0.0012 (5)
C7	0.0171 (6)	0.0267 (7)	0.0206 (6)	−0.0055 (5)	−0.0017 (5)	−0.0039 (5)
C8	0.0199 (7)	0.0202 (6)	0.0230 (7)	−0.0002 (5)	0.0026 (5)	−0.0061 (5)
C9	0.0187 (6)	0.0207 (6)	0.0238 (7)	−0.0006 (5)	0.0018 (5)	−0.0055 (5)
C10	0.0245 (7)	0.0319 (8)	0.0380 (8)	−0.0049 (6)	−0.0002 (6)	0.0069 (6)
C11	0.0291 (8)	0.0367 (8)	0.0363 (8)	0.0007 (6)	−0.0058 (7)	0.0049 (7)
C12	0.0178 (7)	0.0347 (8)	0.0350 (8)	−0.0014 (6)	−0.0014 (6)	−0.0115 (6)
C13	0.0231 (7)	0.0346 (8)	0.0358 (8)	−0.0082 (6)	0.0029 (6)	−0.0029 (6)
C14	0.0244 (7)	0.0276 (7)	0.0275 (7)	−0.0033 (6)	0.0010 (6)	−0.0008 (6)
C15	0.0206 (7)	0.0192 (6)	0.0252 (7)	−0.0008 (5)	0.0045 (5)	−0.0066 (5)
C16	0.0197 (6)	0.0192 (6)	0.0261 (7)	−0.0010 (5)	0.0045 (5)	−0.0064 (5)
C17	0.0244 (7)	0.0256 (7)	0.0332 (8)	−0.0025 (6)	0.0025 (6)	−0.0012 (6)
C18	0.0242 (7)	0.0331 (8)	0.0413 (9)	−0.0104 (6)	0.0064 (6)	−0.0038 (7)
C19	0.0185 (7)	0.0386 (8)	0.0343 (8)	−0.0021 (6)	0.0002 (6)	−0.0102 (6)
C20	0.0254 (7)	0.0341 (8)	0.0300 (8)	0.0014 (6)	−0.0004 (6)	−0.0013 (6)
C21	0.0232 (7)	0.0257 (7)	0.0320 (8)	−0.0030 (6)	0.0041 (6)	−0.0009 (6)
C22	0.0180 (6)	0.0241 (7)	0.0240 (7)	−0.0051 (5)	0.0013 (5)	−0.0032 (5)
C23	0.0186 (6)	0.0189 (6)	0.0270 (7)	−0.0030 (5)	0.0027 (5)	−0.0001 (5)
C24	0.0288 (8)	0.0319 (8)	0.0295 (8)	0.0032 (6)	0.0060 (6)	0.0076 (6)
C25	0.0386 (9)	0.0268 (8)	0.0485 (10)	0.0117 (7)	0.0140 (8)	0.0129 (7)
C26	0.0374 (9)	0.0232 (7)	0.0455 (9)	0.0040 (6)	0.0166 (7)	−0.0017 (6)
C27	0.0326 (8)	0.0313 (8)	0.0295 (8)	0.0000 (6)	0.0063 (6)	−0.0050 (6)
C28	0.0238 (7)	0.0221 (7)	0.0264 (7)	0.0009 (5)	0.0016 (6)	0.0000 (5)

Geometric parameters (Å, º) top

O1—C7	1.2143 (16)	C13—H13	0.95
O2—C22	1.2160 (16)	C14—H14	0.95
N1—C8	1.2878 (17)	C15—C16	1.4733 (18)
N1—N2	1.4173 (15)	C15—C22	1.5216 (19)
N2—C15	1.2877 (17)	C16—C21	1.3922 (19)
C1—C2	1.3839 (19)	C16—C17	1.3955 (19)
C1—C6	1.3920 (18)	C17—C18	1.385 (2)
C1—H1	0.95	C17—H17	0.95
C2—C3	1.385 (2)	C18—C19	1.378 (2)
C2—H2	0.95	C18—H18	0.95
C3—C4	1.384 (2)	C19—C20	1.383 (2)
C3—H3	0.95	C19—H19	0.95
C4—C5	1.377 (2)	C20—C21	1.384 (2)
C4—H4	0.95	C20—H20	0.95
C5—C6	1.3980 (18)	C21—H21	0.95
C5—H5	0.95	C22—C23	1.4890 (18)
C6—C7	1.4814 (18)	C23—C28	1.3902 (19)
C7—C8	1.5185 (18)	C23—C24	1.3959 (19)
C8—C9	1.4727 (18)	C24—C25	1.383 (2)
C9—C10	1.3908 (19)	C24—H24	0.95
C9—C14	1.3929 (19)	C25—C26	1.381 (2)
C10—C11	1.380 (2)	C25—H25	0.95
C10—H10	0.95	C26—C27	1.381 (2)
C11—C12	1.385 (2)	C26—H26	0.95
C11—H11	0.95	C27—C28	1.3869 (19)
C12—C13	1.379 (2)	C27—H27	0.95
C12—H12	0.95	C28—H28	0.95
C13—C14	1.386 (2)

C8—N1—N2	110.97 (11)	C9—C14—H14	119.9
C15—N2—N1	111.78 (11)	N2—C15—C16	119.72 (12)
C2—C1—C6	119.77 (13)	N2—C15—C22	122.16 (12)
C2—C1—H1	120.1	C16—C15—C22	118.06 (11)
C6—C1—H1	120.1	C21—C16—C17	119.04 (12)
C1—C2—C3	119.93 (14)	C21—C16—C15	120.20 (12)
C1—C2—H2	120.0	C17—C16—C15	120.75 (12)
C3—C2—H2	120.0	C18—C17—C16	120.00 (14)
C4—C3—C2	120.32 (14)	C18—C17—H17	120.0
C4—C3—H3	119.8	C16—C17—H17	120.0
C2—C3—H3	119.8	C19—C18—C17	120.34 (13)
C5—C4—C3	120.37 (14)	C19—C18—H18	119.8
C5—C4—H4	119.8	C17—C18—H18	119.8
C3—C4—H4	119.8	C18—C19—C20	120.25 (13)
C4—C5—C6	119.54 (14)	C18—C19—H19	119.9
C4—C5—H5	120.2	C20—C19—H19	119.9
C6—C5—H5	120.2	C19—C20—C21	119.76 (14)
C1—C6—C5	120.06 (13)	C19—C20—H20	120.1
C1—C6—C7	120.21 (12)	C21—C20—H20	120.1
C5—C6—C7	119.71 (12)	C20—C21—C16	120.61 (13)
O1—C7—C6	122.57 (13)	C20—C21—H21	119.7
O1—C7—C8	119.13 (12)	C16—C21—H21	119.7
C6—C7—C8	118.18 (11)	O2—C22—C23	122.88 (13)
N1—C8—C9	119.89 (12)	O2—C22—C15	120.51 (12)
N1—C8—C7	122.21 (12)	C23—C22—C15	116.58 (11)
C9—C8—C7	117.89 (11)	C28—C23—C24	119.31 (12)
C10—C9—C14	118.78 (12)	C28—C23—C22	120.68 (12)
C10—C9—C8	120.25 (12)	C24—C23—C22	120.01 (12)
C14—C9—C8	120.96 (12)	C25—C24—C23	119.74 (14)
C11—C10—C9	120.80 (14)	C25—C24—H24	120.1
C11—C10—H10	119.6	C23—C24—H24	120.1
C9—C10—H10	119.6	C26—C25—C24	120.49 (14)
C10—C11—C12	119.94 (14)	C26—C25—H25	119.8
C10—C11—H11	120.0	C24—C25—H25	119.8
C12—C11—H11	120.0	C25—C26—C27	120.26 (14)
C13—C12—C11	119.90 (13)	C25—C26—H26	119.9
C13—C12—H12	120.0	C27—C26—H26	119.9
C11—C12—H12	120.0	C26—C27—C28	119.63 (14)
C12—C13—C14	120.27 (14)	C26—C27—H27	120.2
C12—C13—H13	119.9	C28—C27—H27	120.2
C14—C13—H13	119.9	C23—C28—C27	120.55 (13)
C13—C14—C9	120.30 (13)	C23—C28—H28	119.7
C13—C14—H14	119.9	C27—C28—H28	119.7

C8—N1—N2—C15	177.82 (12)	N1—N2—C15—C16	−177.87 (11)
C6—C1—C2—C3	0.1 (2)	N1—N2—C15—C22	−0.55 (17)
C1—C2—C3—C4	0.1 (2)	N2—C15—C16—C21	13.52 (19)
C2—C3—C4—C5	−0.5 (2)	C22—C15—C16—C21	−163.92 (12)
C3—C4—C5—C6	0.8 (2)	N2—C15—C16—C17	−167.62 (13)
C2—C1—C6—C5	0.20 (19)	C22—C15—C16—C17	14.95 (18)
C2—C1—C6—C7	179.23 (12)	C21—C16—C17—C18	0.1 (2)
C4—C5—C6—C1	−0.6 (2)	C15—C16—C17—C18	−178.82 (13)
C4—C5—C6—C7	−179.66 (12)	C16—C17—C18—C19	−0.1 (2)
C1—C6—C7—O1	−171.53 (13)	C17—C18—C19—C20	−0.1 (2)
C5—C6—C7—O1	7.51 (19)	C18—C19—C20—C21	0.2 (2)
C1—C6—C7—C8	4.51 (18)	C19—C20—C21—C16	−0.2 (2)
C5—C6—C7—C8	−176.45 (12)	C17—C16—C21—C20	0.1 (2)
N2—N1—C8—C9	177.59 (11)	C15—C16—C21—C20	178.98 (12)
N2—N1—C8—C7	−2.72 (17)	N2—C15—C22—O2	91.73 (16)
O1—C7—C8—N1	−93.45 (16)	C16—C15—C22—O2	−90.91 (15)
C6—C7—C8—N1	90.38 (15)	N2—C15—C22—C23	−90.28 (15)
O1—C7—C8—C9	86.25 (15)	C16—C15—C22—C23	87.09 (14)
C6—C7—C8—C9	−89.92 (14)	O2—C22—C23—C28	169.79 (13)
N1—C8—C9—C10	−15.03 (19)	C15—C22—C23—C28	−8.15 (18)
C7—C8—C9—C10	165.26 (12)	O2—C22—C23—C24	−10.4 (2)
N1—C8—C9—C14	165.69 (13)	C15—C22—C23—C24	171.70 (12)
C7—C8—C9—C14	−14.01 (18)	C28—C23—C24—C25	1.4 (2)
C14—C9—C10—C11	−0.2 (2)	C22—C23—C24—C25	−178.43 (13)
C8—C9—C10—C11	−179.45 (13)	C23—C24—C25—C26	−1.6 (2)
C9—C10—C11—C12	−0.3 (2)	C24—C25—C26—C27	0.5 (2)
C10—C11—C12—C13	0.2 (2)	C25—C26—C27—C28	0.7 (2)
C11—C12—C13—C14	0.4 (2)	C24—C23—C28—C27	−0.2 (2)
C12—C13—C14—C9	−0.8 (2)	C22—C23—C28—C27	179.65 (13)
C10—C9—C14—C13	0.7 (2)	C26—C27—C28—C23	−0.9 (2)
C8—C9—C14—C13	−179.97 (13)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C1—H1···O1ⁱ	0.95	2.24	3.0832 (16)	147
C13—H13···Cg1ⁱⁱ	0.95	2.68	3.5705 (16)	157
C18—H18···Cg2ⁱⁱⁱ	0.95	2.66	3.5304 (16)	153

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

Experimental details

Crystal data
Chemical formula	C₂₈H₂₀N₂O₂
M_r	416.46
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	140
a, b, c (Å)	8.2875 (2), 22.1023 (4), 11.6602 (2)
β (°)	97.539 (1)
V (Å³)	2117.37 (7)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.08
Crystal size (mm)	0.30 × 0.04 × 0.03

Data collection
Diffractometer	Bruker SMART APEX area-detector diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	17323, 4857, 3510
R_int	0.030
(sin θ/λ)_max (Å⁻¹)	0.650

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.040, 0.107, 1.03
No. of reflections	4857
No. of parameters	289
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.24, −0.21

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C1—H1···O1ⁱ	0.95	2.24	3.0832 (16)	147
C13—H13···Cg1ⁱⁱ	0.95	2.68	3.5705 (16)	157
C18—H18···Cg2ⁱⁱⁱ	0.95	2.66	3.5304 (16)	153

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

Acknowledgements

The authors thank Vijaygarh Jyotish Ray College and the University of Malaya for supporting this study.

References

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Bruker (2008). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Ibata, T. & Singh, G. S. (1994). Tetrahedron Lett. 35, 2581–2584. CrossRef CAS Web of Science Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Singh, S. B. (1983). Indian J. Chem. Sect. B, 20, 810. Google Scholar
Westrip, S. P. (2009). publCIF. In preparation. Google Scholar