3-(7,8,13,14-Tetra­hydrodi­benzo­[a,i]phen­an­thridin-5-yl)benzene-1,2-diol

Karthikeyan, N.S.; Ramachandran, G.; Sathiyanarayanan, K.; Raghavaiah, P.; Rathore, R.S.

doi:10.1107/S1600536810023688

organic compounds

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ISSN: 2056-9890

Volume 66| Part 7| July 2010| Page o1753

doi:10.1107/S1600536810023688

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3-(7,8,13,14-Tetrahydrodibenzo[a,i]phenanthridin-5-yl)benzene-1,2-diol

N. S. Karthikeyan,^a G. Ramachandran,^a K. Sathiyanarayanan,^a P. Raghavaiah ^b and R. S. Rathore ^c ^*

^aChemistry Division, School of Advanced Sciences, VIT University, Vellore 632014, India, ^bSchool of Chemistry, University of Hyderabad, Hyderabad 500046, India, and ^cBioinformatics Infrastructure Facility, Department of Biotechnology, School of Life Science, University of Hyderabad, Hyderabad 500046, India
^*Correspondence e-mail: ravindranath_rathore@yahoo.com

(Received 13 June 2010; accepted 18 June 2010; online 23 June 2010)

In the title compound, C₂₇H₂₁NO₂, the half-chair conformation of the alicyclic rings gives rise to a slightly folded structure of the central tricyclic tetrahydrophenanthridine unit. Tandem intramolecular O—H⋯N and O—H⋯O hydrogen bonds give rise to adjacent S(6) and S(5) rings, respectively, which dictate the conformation of the 5-aryl substituent. In the crystal structure, an intermolecular C—H⋯O contact generates chains parallel to [101]. Short O—H⋯π and C—H⋯π contacts are also observed.

Related literature

For the medicinal and optoelectronic applications of phenanthridine derivatives and for related structures, see: Sathiyanarayanan et al. (2009 ); Rathore et al. (2010a ,b ). For their synthesis, see: Sathiyanarayanan et al. (2009); Karthikeyan et al. (2009 ).

Experimental

Crystal data

C₂₇H₂₁NO₂
M_r = 391.45
Monoclinic, P 2₁ /n
a = 11.4002 (10) Å
b = 10.2254 (7) Å
c = 17.3674 (16) Å
β = 106.188 (10)°
V = 1944.3 (3) Å³
Z = 4
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 294 K
0.42 × 0.36 × 0.20 mm

Data collection

Oxford Diffraction Xcalibur Eos Gemini diffractometer
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2009 $[Oxford Diffraction (2009). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, UK.]$ ) T_min = 0.966, T_max = 0.983
9150 measured reflections
3974 independent reflections
2174 reflections with I > 2σ(I)
R_int = 0.036

Refinement

R[F² > 2σ(F²)] = 0.042
wR(F²) = 0.092
S = 0.86
3974 reflections
273 parameters
H-atom parameters constrained
Δρ_max = 0.15 e Å⁻³
Δρ_min = −0.19 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

Cg3 is the centroid of the C4–C9 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯N1	0.82	1.92	2.616 (2)	142
O2—H2⋯O1	0.82	2.20	2.659 (2)	115
C8—H8⋯O2ⁱ	0.93	2.60	3.245 (2)	127
O2—H2⋯Cg3ⁱⁱ	0.82	2.99	3.6649 (14)	142
C26—H26⋯Cg3ⁱⁱⁱ	0.93	2.92	3.6663 (19)	139
Symmetry codes: (i) $[x+{\script{1\over 2}}, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]$ ; (ii) -x+1, -y, -z+2; (iii) -x+1, -y+1, -z+2.

Data collection: CrysAlis PRO (Oxford Diffraction, 2009 $[Oxford Diffraction (2009). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, UK.]$ ); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997 ) and PLATON (Spek, 2009 ); software used to prepare material for publication: SHELXL97 and PLATON.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810023688/bh2296sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536810023688/bh2296Isup2.hkl

checkCIF report

Comment top

Phenanthridine derivatives are attractive candidates for medicinal and optoelectronic applications (Sathiyanarayanan et al., 2009; Rathore et al., 2010a,b). Following our new high-yielding synthetic procedure of simultaneous synthesis of phenanthridine and azabicyclo[3.3.1]nonanone, involving one-step process using tetralone and substituted benzaldehydes (Sathiyanarayanan et al., 2009; Karthikeyan et al., 2009), a series of one of its important pentacyclic derivative i.e., 5-aryl-7,8,13,14-tetrahydro-dibenzo[a,i]phenanthridine (5ATDP) were prepared. In the present work, 5-(2,3-dihydroxyphenyl)-7,8,13,14-tetrahydro-dibenzo[a,i]phenanthridine, (I), is examined. The ring nomenclature, P1—P5 is illustrated in Supplementary Fig. 3.

The structure of (I) with adopted atom-numbering scheme is shown in Fig. 1. Alicyclic P2 (C1—C3/C4/C9/C10) and P4 (C11—C13/C14/C19/C20) rings adopt a half-chair (C2) conformation. Ring puckering parameters are as follows: ring-P2: q₂ = 0.5127 (19) Å, q₃ = -0.1717 (19) Å, θ = 108.5 (2)°, ϕ = 273.1 (2)°, and total puckering amplitude, Q = 0.5409 (19) Å; ring-P4: q₂ = 0.5427 (18) Å, q₃ = -0.1448 (18) Å, θ = 104.94 (18)°, ϕ = 278.09 (19)°, and total puckering amplitude, Q = 0.5617 (18) Å. The puckering of P2 and P4 leads to a slightly folded structure of central tetrahydro-phenanthridine tricyclic ring (N1/C1—C4/C9—C14/C19—C21), a characteristic feature among previously investigated 5ATDP analogs (Sathiyanarayanan et al., 2009; Rathore et al., 2010a).

All previously investigated 5ATDP compounds are characterized by the only plausible, cooperative C—H···N bonded R²₂(14) closed dimers – between axial H atom of alicyclic-P4 ring and pyridine N – and these interactions are sometimes augmented by C—H···π interactions (Sathiyanarayanan et al., 2009; Rathore et al., 2010a). In contrast, the packing arrangement in (I) is different due to the presence of two strong hydroxyl donors. Two tandem intramolecular hydrogen bonds, namely O1—H1···N1 and O2—H2···O1 form hydrogen bonded two adjacent S(6) and S(5) rings (Fig. 1). The intramolecular hydrogen bonds dictate the conformation of 5-aryl substituent. An intermolecular C8—H8···O2ⁱ [symmetry code (ii): 1/2 + x, 1/2 - y, -1/2 + z] hydrogen bond give rise to a molecular one-dimensional C(11) chain, parallel to [1 0 1] (Fig. 2). Two short contacts, O2—H2···.Cg3ⁱⁱ [symmetry code (ii): 1 - x, -y, 2 - z] and C26—H26···Cg3ⁱⁱⁱ [symmetry code (iii): 1 - x, 1 - y, 2 - z] are also observed in the crystal structure (Cg3 is the centroids of (C4—C9) ring).

Related literature top

For the medicinal and optoelectronic applications of phenanthridine derivatives and for related structures, see: Sathiyanarayanan et al. (2009); Rathore et al. (2010a,b). For their synthesis, see: Sathiyanarayanan et al. (2009); Karthikeyan et al. (2009).

Experimental top

A mixture of 2-tetralone (0.01 mol) and 2,3-dihydroxy benzaldehyde (0.02 mol) was added to a warm solution of ammonium acetate (0.01 mol) in absolute ethanol (15 ml). The mixture was gently warmed on a water bath until the yellow colour changed to orange and then kept aside for overnight at room temperature. The completion of the reaction was identified with TLC. The solid obtained was separated and the crude compound was purified by silica gel column chromatography with hexane and ethyl acetate as eluant. Suitable single crystals for data collection were grown from ethanol and tetrahydrofuran mixture (in 1:1 ratio). Yield, 66°, m.p. 266–268 °C.

Computing details top

Data collection: CrysAlis PRO (Oxford Diffraction, 2009); cell refinement: CrysAlis PRO (Oxford Diffraction, 2009); data reduction: CrysAlis PRO (Oxford Diffraction, 2009); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997) and PLATON (Spek, 2009); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009).

Figures top

	Fig. 1. A view of (I) with non-H atoms shown as probability ellipsoids at 30% level (Farrugia, 1997). H atoms radii are on an arbitrary scale. Dashed lines indicate intra-molecular hydrogen bonds.
	Fig. 2. C—H···O bonded C(11) linear chain along along [1 0 1]-axis.
	Fig. 3. The ring nomenclature, P1—P5, adopted for (I).

3-(7,8,13,14-Tetrahydrodibenzo[a,i]phenanthridin-5-yl)benzene- 1,2-diol top

Crystal data top

C₂₇H₂₁NO₂	F(000) = 824
M_r = 391.45	D_x = 1.337 Mg m⁻³
Monoclinic, P2₁/n	Melting point: 540(2) K
Hall symbol: -P 2yn	Mo Kα radiation, λ = 0.71073 Å
a = 11.4002 (10) Å	Cell parameters from 2754 reflections
b = 10.2254 (7) Å	θ = 2.7–28.9°
c = 17.3674 (16) Å	µ = 0.08 mm⁻¹
β = 106.188 (10)°	T = 294 K
V = 1944.3 (3) Å³	Plate, colourless
Z = 4	0.42 × 0.36 × 0.20 mm

Data collection top

Oxford Diffraction Xcalibur Eos Gemini diffractometer	3974 independent reflections
Radiation source: Enhance (Mo) X-ray Source	2174 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.036
Detector resolution: 16.3291 pixels mm^-1	θ_max = 26.4°, θ_min = 2.7°
ω scan	h = −14→14
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2009)	k = −9→12
T_min = 0.966, T_max = 0.983	l = −21→21
9150 measured reflections

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)] = 0.042	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.092	H-atom parameters constrained
S = 0.86	w = 1/[σ²(F_o²) + (0.0412P)²] where P = (F_o² + 2F_c²)/3
3974 reflections	(Δ/σ)_max < 0.001
273 parameters	Δρ_max = 0.15 e Å⁻³
0 restraints	Δρ_min = −0.19 e Å⁻³
0 constraints

Crystal data top

C₂₇H₂₁NO₂	V = 1944.3 (3) Å³
M_r = 391.45	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 11.4002 (10) Å	µ = 0.08 mm⁻¹
b = 10.2254 (7) Å	T = 294 K
c = 17.3674 (16) Å	0.42 × 0.36 × 0.20 mm
β = 106.188 (10)°

Data collection top

Oxford Diffraction Xcalibur Eos Gemini diffractometer	3974 independent reflections
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2009)	2174 reflections with I > 2σ(I)
T_min = 0.966, T_max = 0.983	R_int = 0.036
9150 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.042	0 restraints
wR(F²) = 0.092	H-atom parameters constrained
S = 0.86	Δρ_max = 0.15 e Å⁻³
3974 reflections	Δρ_min = −0.19 e Å⁻³
273 parameters

Special details top

Experimental. CrysAlis PRO, Oxford Diffraction Ltd., Version 1.171.33.55 (release 05–01-2010 CrysAlis171. NET) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.

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

	x	y	z	U_iso*/U_eq
C1	0.58139 (16)	0.19964 (15)	1.00791 (11)	0.0382 (4)
C2	0.68255 (16)	0.12360 (17)	1.06347 (11)	0.0519 (5)
H2A	0.6793	0.0332	1.0460	0.062*
H2B	0.6730	0.1253	1.1172	0.062*
C3	0.80504 (17)	0.18322 (18)	1.06389 (11)	0.0517 (5)
H3A	0.8109	0.2715	1.0850	0.062*
H3B	0.8710	0.1319	1.0978	0.062*
C4	0.81547 (16)	0.18521 (14)	0.98005 (11)	0.0398 (4)
C5	0.92342 (16)	0.15038 (15)	0.96280 (12)	0.0471 (5)
H5	0.9921	0.1306	1.0046	0.057*
C6	0.93057 (17)	0.14457 (15)	0.88518 (13)	0.0508 (5)
H6	1.0037	0.1222	0.8748	0.061*
C7	0.82859 (17)	0.17209 (16)	0.82289 (12)	0.0483 (5)
H7	0.8325	0.1670	0.7702	0.058*
C8	0.72046 (16)	0.20723 (14)	0.83870 (11)	0.0417 (4)
H8	0.6519	0.2245	0.7962	0.050*
C9	0.71229 (15)	0.21729 (14)	0.91707 (10)	0.0351 (4)
C10	0.59725 (15)	0.25250 (14)	0.93686 (10)	0.0341 (4)
C11	0.50312 (15)	0.33225 (14)	0.89077 (10)	0.0335 (4)
C12	0.51453 (15)	0.40983 (14)	0.81910 (10)	0.0400 (4)
H12A	0.4838	0.3582	0.7708	0.048*
H12B	0.5999	0.4290	0.8250	0.048*
C13	0.44307 (16)	0.53713 (15)	0.81136 (11)	0.0445 (5)
H13A	0.4774	0.5918	0.8578	0.053*
H13B	0.4488	0.5842	0.7640	0.053*
C14	0.31175 (16)	0.50795 (15)	0.80502 (10)	0.0369 (4)
C15	0.21463 (18)	0.56693 (17)	0.74949 (11)	0.0475 (5)
H15	0.2296	0.6340	0.7173	0.057*
C16	0.09624 (19)	0.52755 (17)	0.74136 (12)	0.0529 (5)
H16	0.0321	0.5689	0.7043	0.063*
C17	0.07236 (17)	0.42738 (17)	0.78777 (12)	0.0496 (5)
H17	−0.0073	0.3987	0.7810	0.059*
C18	0.16807 (16)	0.36996 (16)	0.84443 (11)	0.0425 (5)
H18	0.1520	0.3028	0.8761	0.051*
C19	0.28837 (15)	0.41046 (14)	0.85521 (10)	0.0348 (4)
C20	0.39375 (15)	0.34712 (14)	0.91349 (10)	0.0337 (4)
C21	0.38970 (15)	0.29631 (14)	0.98754 (10)	0.0352 (4)
C22	0.29358 (15)	0.32283 (14)	1.02851 (10)	0.0355 (4)
C23	0.26657 (16)	0.23013 (15)	1.07973 (10)	0.0375 (4)
C24	0.17524 (16)	0.25250 (16)	1.11694 (10)	0.0408 (4)
C25	0.11592 (16)	0.37071 (16)	1.10857 (11)	0.0474 (5)
H25	0.0549	0.3856	1.1336	0.057*
C26	0.14778 (17)	0.46731 (17)	1.06260 (12)	0.0476 (5)
H26	0.1104	0.5488	1.0586	0.057*
C27	0.23424 (15)	0.44406 (15)	1.02280 (11)	0.0424 (4)
H27	0.2538	0.5099	0.9915	0.051*
N1	0.48233 (13)	0.22200 (12)	1.03236 (8)	0.0405 (4)
O1	0.32438 (12)	0.11211 (10)	1.09616 (8)	0.0547 (4)
H1	0.3904	0.1158	1.0861	0.082*
O2	0.14479 (13)	0.15665 (11)	1.16295 (8)	0.0580 (4)
H2	0.1878	0.0922	1.1635	0.087*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0440 (11)	0.0378 (9)	0.0325 (10)	0.0032 (8)	0.0105 (9)	0.0031 (8)
C2	0.0597 (13)	0.0584 (11)	0.0388 (12)	0.0166 (10)	0.0157 (10)	0.0142 (10)
C3	0.0477 (13)	0.0604 (11)	0.0404 (12)	0.0116 (10)	0.0012 (10)	0.0030 (10)
C4	0.0427 (11)	0.0352 (9)	0.0386 (11)	0.0000 (8)	0.0066 (9)	0.0007 (8)
C5	0.0367 (11)	0.0421 (10)	0.0568 (14)	0.0028 (9)	0.0034 (10)	0.0006 (10)
C6	0.0399 (12)	0.0502 (11)	0.0664 (15)	0.0017 (9)	0.0215 (11)	0.0029 (11)
C7	0.0475 (12)	0.0541 (11)	0.0493 (13)	0.0027 (10)	0.0232 (11)	0.0031 (10)
C8	0.0386 (11)	0.0458 (10)	0.0413 (12)	0.0008 (9)	0.0119 (9)	0.0046 (9)
C9	0.0363 (10)	0.0319 (9)	0.0357 (11)	−0.0016 (8)	0.0078 (9)	0.0011 (8)
C10	0.0359 (10)	0.0349 (9)	0.0312 (10)	−0.0016 (8)	0.0086 (8)	−0.0001 (8)
C11	0.0374 (10)	0.0345 (9)	0.0282 (10)	−0.0033 (8)	0.0087 (8)	0.0003 (8)
C12	0.0384 (11)	0.0482 (10)	0.0355 (11)	0.0016 (8)	0.0138 (9)	0.0090 (9)
C13	0.0500 (12)	0.0440 (10)	0.0404 (11)	−0.0002 (9)	0.0143 (10)	0.0101 (9)
C14	0.0432 (11)	0.0348 (9)	0.0327 (10)	0.0029 (8)	0.0105 (9)	−0.0012 (8)
C15	0.0566 (13)	0.0459 (11)	0.0415 (12)	0.0114 (10)	0.0162 (11)	0.0074 (9)
C16	0.0505 (13)	0.0598 (12)	0.0427 (12)	0.0192 (10)	0.0036 (10)	0.0024 (10)
C17	0.0365 (11)	0.0591 (12)	0.0509 (13)	0.0032 (9)	0.0086 (10)	−0.0072 (10)
C18	0.0397 (11)	0.0449 (10)	0.0438 (12)	−0.0003 (9)	0.0131 (9)	−0.0013 (9)
C19	0.0387 (11)	0.0357 (9)	0.0304 (10)	0.0033 (8)	0.0102 (8)	−0.0022 (8)
C20	0.0368 (10)	0.0321 (9)	0.0322 (10)	−0.0031 (8)	0.0096 (8)	0.0006 (8)
C21	0.0406 (11)	0.0322 (9)	0.0339 (10)	−0.0021 (8)	0.0123 (9)	0.0016 (8)
C22	0.0401 (11)	0.0364 (9)	0.0320 (10)	−0.0022 (8)	0.0131 (8)	−0.0011 (8)
C23	0.0459 (11)	0.0356 (10)	0.0329 (10)	−0.0008 (8)	0.0142 (9)	−0.0036 (8)
C24	0.0483 (12)	0.0451 (10)	0.0309 (10)	−0.0119 (9)	0.0140 (9)	−0.0061 (8)
C25	0.0459 (12)	0.0535 (11)	0.0491 (13)	−0.0033 (10)	0.0235 (10)	−0.0110 (10)
C26	0.0479 (12)	0.0435 (10)	0.0534 (13)	0.0028 (9)	0.0171 (10)	−0.0061 (10)
C27	0.0452 (11)	0.0385 (9)	0.0442 (12)	−0.0013 (9)	0.0134 (9)	0.0003 (9)
N1	0.0468 (10)	0.0415 (8)	0.0358 (9)	0.0038 (7)	0.0160 (8)	0.0050 (7)
O1	0.0700 (10)	0.0442 (7)	0.0605 (10)	0.0078 (7)	0.0356 (8)	0.0108 (6)
O2	0.0769 (11)	0.0544 (7)	0.0543 (9)	−0.0078 (7)	0.0374 (8)	0.0032 (7)

Geometric parameters (Å, º) top

C1—N1	1.332 (2)	C13—H13B	0.9700
C1—C10	1.404 (2)	C14—C15	1.387 (2)
C1—C2	1.498 (2)	C14—C19	1.398 (2)
C2—C3	1.522 (2)	C15—C16	1.377 (2)
C2—H2A	0.9700	C15—H15	0.9300
C2—H2B	0.9700	C16—C17	1.377 (2)
C3—C4	1.494 (2)	C16—H16	0.9300
C3—H3A	0.9700	C17—C18	1.380 (2)
C3—H3B	0.9700	C17—H17	0.9300
C4—C5	1.392 (2)	C18—C19	1.394 (2)
C4—C9	1.404 (2)	C18—H18	0.9300
C5—C6	1.374 (3)	C19—C20	1.486 (2)
C5—H5	0.9300	C20—C21	1.400 (2)
C6—C7	1.378 (2)	C21—N1	1.357 (2)
C6—H6	0.9300	C21—C22	1.488 (2)
C7—C8	1.383 (2)	C22—C23	1.392 (2)
C7—H7	0.9300	C22—C27	1.402 (2)
C8—C9	1.394 (2)	C23—O1	1.3665 (18)
C8—H8	0.9300	C23—C24	1.389 (2)
C9—C10	1.490 (2)	C24—O2	1.3691 (19)
C10—C11	1.406 (2)	C24—C25	1.373 (2)
C11—C20	1.417 (2)	C25—C26	1.381 (2)
C11—C12	1.512 (2)	C25—H25	0.9300
C12—C13	1.522 (2)	C26—C27	1.373 (2)
C12—H12A	0.9700	C26—H26	0.9300
C12—H12B	0.9700	C27—H27	0.9300
C13—C14	1.500 (2)	O1—H1	0.8200
C13—H13A	0.9700	O2—H2	0.8200

N1—C1—C10	122.83 (16)	C14—C13—H13B	109.8
N1—C1—C2	116.89 (16)	C12—C13—H13B	109.8
C10—C1—C2	120.08 (16)	H13A—C13—H13B	108.2
C1—C2—C3	109.61 (14)	C15—C14—C19	119.31 (17)
C1—C2—H2A	109.7	C15—C14—C13	123.46 (16)
C3—C2—H2A	109.7	C19—C14—C13	117.12 (16)
C1—C2—H2B	109.7	C16—C15—C14	120.90 (17)
C3—C2—H2B	109.7	C16—C15—H15	119.5
H2A—C2—H2B	108.2	C14—C15—H15	119.5
C4—C3—C2	108.85 (15)	C17—C16—C15	120.36 (18)
C4—C3—H3A	109.9	C17—C16—H16	119.8
C2—C3—H3A	109.9	C15—C16—H16	119.8
C4—C3—H3B	109.9	C16—C17—C18	119.20 (18)
C2—C3—H3B	109.9	C16—C17—H17	120.4
H3A—C3—H3B	108.3	C18—C17—H17	120.4
C5—C4—C9	119.42 (17)	C17—C18—C19	121.45 (17)
C5—C4—C3	121.46 (16)	C17—C18—H18	119.3
C9—C4—C3	119.05 (16)	C19—C18—H18	119.3
C6—C5—C4	121.34 (18)	C18—C19—C14	118.65 (16)
C6—C5—H5	119.3	C18—C19—C20	122.68 (15)
C4—C5—H5	119.3	C14—C19—C20	118.49 (15)
C5—C6—C7	119.57 (17)	C21—C20—C11	118.24 (15)
C5—C6—H6	120.2	C21—C20—C19	124.05 (15)
C7—C6—H6	120.2	C11—C20—C19	117.64 (15)
C6—C7—C8	120.04 (18)	N1—C21—C20	121.02 (15)
C6—C7—H7	120.0	N1—C21—C22	112.76 (15)
C8—C7—H7	120.0	C20—C21—C22	126.08 (15)
C7—C8—C9	121.27 (17)	C23—C22—C27	117.31 (15)
C7—C8—H8	119.4	C23—C22—C21	120.33 (14)
C9—C8—H8	119.4	C27—C22—C21	122.15 (14)
C8—C9—C4	118.30 (16)	O1—C23—C24	115.39 (14)
C8—C9—C10	123.09 (16)	O1—C23—C22	123.72 (15)
C4—C9—C10	118.50 (16)	C24—C23—C22	120.88 (15)
C1—C10—C11	117.29 (15)	O2—C24—C25	119.64 (16)
C1—C10—C9	116.55 (15)	O2—C24—C23	119.91 (15)
C11—C10—C9	126.15 (15)	C25—C24—C23	120.45 (16)
C10—C11—C20	119.65 (15)	C24—C25—C26	119.33 (17)
C10—C11—C12	123.07 (15)	C24—C25—H25	120.3
C20—C11—C12	117.22 (14)	C26—C25—H25	120.3
C11—C12—C13	110.78 (13)	C27—C26—C25	120.57 (16)
C11—C12—H12A	109.5	C27—C26—H26	119.7
C13—C12—H12A	109.5	C25—C26—H26	119.7
C11—C12—H12B	109.5	C26—C27—C22	121.15 (16)
C13—C12—H12B	109.5	C26—C27—H27	119.4
H12A—C12—H12B	108.1	C22—C27—H27	119.4
C14—C13—C12	109.58 (13)	C1—N1—C21	120.44 (15)
C14—C13—H13A	109.8	C23—O1—H1	109.5
C12—C13—H13A	109.8	C24—O2—H2	109.5

N1—C1—C2—C3	−139.21 (16)	C17—C18—C19—C20	−177.56 (15)
C10—C1—C2—C3	35.8 (2)	C15—C14—C19—C18	3.9 (2)
C1—C2—C3—C4	−56.87 (18)	C13—C14—C19—C18	−172.52 (15)
C2—C3—C4—C5	−137.29 (16)	C15—C14—C19—C20	179.13 (15)
C2—C3—C4—C9	39.81 (19)	C13—C14—C19—C20	2.7 (2)
C9—C4—C5—C6	−1.1 (2)	C10—C11—C20—C21	8.8 (2)
C3—C4—C5—C6	175.97 (15)	C12—C11—C20—C21	−168.34 (14)
C4—C5—C6—C7	−0.8 (3)	C10—C11—C20—C19	−168.43 (14)
C5—C6—C7—C8	1.0 (3)	C12—C11—C20—C19	14.5 (2)
C6—C7—C8—C9	0.8 (2)	C18—C19—C20—C21	−34.8 (2)
C7—C8—C9—C4	−2.8 (2)	C14—C19—C20—C21	150.12 (15)
C7—C8—C9—C10	−178.89 (14)	C18—C19—C20—C11	142.20 (16)
C5—C4—C9—C8	2.9 (2)	C14—C19—C20—C11	−32.9 (2)
C3—C4—C9—C8	−174.29 (14)	C11—C20—C21—N1	−7.4 (2)
C5—C4—C9—C10	179.17 (13)	C19—C20—C21—N1	169.61 (14)
C3—C4—C9—C10	2.0 (2)	C11—C20—C21—C22	167.95 (14)
N1—C1—C10—C11	0.1 (2)	C19—C20—C21—C22	−15.1 (2)
C2—C1—C10—C11	−174.64 (14)	N1—C21—C22—C23	−32.9 (2)
N1—C1—C10—C9	−179.29 (14)	C20—C21—C22—C23	151.40 (16)
C2—C1—C10—C9	6.0 (2)	N1—C21—C22—C27	141.72 (16)
C8—C9—C10—C1	149.50 (15)	C20—C21—C22—C27	−33.9 (2)
C4—C9—C10—C1	−26.6 (2)	C27—C22—C23—O1	−174.59 (15)
C8—C9—C10—C11	−29.8 (2)	C21—C22—C23—O1	0.3 (3)
C4—C9—C10—C11	154.06 (15)	C27—C22—C23—C24	6.5 (3)
C1—C10—C11—C20	−5.2 (2)	C21—C22—C23—C24	−178.57 (15)
C9—C10—C11—C20	174.09 (14)	O1—C23—C24—O2	−3.2 (2)
C1—C10—C11—C12	171.70 (15)	C22—C23—C24—O2	175.78 (16)
C9—C10—C11—C12	−9.0 (2)	O1—C23—C24—C25	176.16 (16)
C10—C11—C12—C13	−147.04 (15)	C22—C23—C24—C25	−4.9 (3)
C20—C11—C12—C13	29.9 (2)	O2—C24—C25—C26	179.48 (17)
C11—C12—C13—C14	−57.30 (19)	C23—C24—C25—C26	0.1 (3)
C12—C13—C14—C15	−134.66 (16)	C24—C25—C26—C27	2.7 (3)
C12—C13—C14—C19	41.6 (2)	C25—C26—C27—C22	−0.9 (3)
C19—C14—C15—C16	−2.3 (3)	C23—C22—C27—C26	−3.7 (3)
C13—C14—C15—C16	173.86 (16)	C21—C22—C27—C26	−178.51 (17)
C14—C15—C16—C17	−0.8 (3)	C10—C1—N1—C21	1.4 (2)
C15—C16—C17—C18	2.2 (3)	C2—C1—N1—C21	176.29 (14)
C16—C17—C18—C19	−0.5 (3)	C20—C21—N1—C1	2.4 (2)
C17—C18—C19—C14	−2.5 (2)	C22—C21—N1—C1	−173.55 (14)

Hydrogen-bond geometry (Å, º) top

Cg3 is the centroid of C4–C9 ring.

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N1	0.82	1.92	2.616 (2)	142
O2—H2···O1	0.82	2.20	2.659 (2)	115
C8—H8···O2ⁱ	0.93	2.60	3.245 (2)	127
O2—H2···Cg3ⁱⁱ	0.82	2.99	3.6649 (14)	142
C26—H26···Cg3ⁱⁱⁱ	0.93	2.92	3.6663 (19)	139

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

Experimental details

Crystal data
Chemical formula	C₂₇H₂₁NO₂
M_r	391.45
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	294
a, b, c (Å)	11.4002 (10), 10.2254 (7), 17.3674 (16)
β (°)	106.188 (10)
V (Å³)	1944.3 (3)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.08
Crystal size (mm)	0.42 × 0.36 × 0.20

Data collection
Diffractometer	Oxford Diffraction Xcalibur Eos Gemini diffractometer
Absorption correction	Multi-scan (CrysAlis PRO; Oxford Diffraction, 2009)
T_min, T_max	0.966, 0.983
No. of measured, independent and observed [I > 2σ(I)] reflections	9150, 3974, 2174
R_int	0.036
(sin θ/λ)_max (Å⁻¹)	0.625

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.042, 0.092, 0.86
No. of reflections	3974
No. of parameters	273
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.15, −0.19

Computer programs: CrysAlis PRO (Oxford Diffraction, 2009), SHELXS97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997) and PLATON (Spek, 2009), SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

Cg3 is the centroid of C4–C9 ring.

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N1	0.82	1.92	2.616 (2)	142
O2—H2···O1	0.82	2.20	2.659 (2)	115
C8—H8···O2ⁱ	0.93	2.60	3.245 (2)	127
O2—H2···Cg3ⁱⁱ	0.82	2.99	3.6649 (14)	142
C26—H26···Cg3ⁱⁱⁱ	0.93	2.92	3.6663 (19)	139

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

Acknowledgements

The Bioinformatics Infrastructure Facility and the Single Crystal X-ray Diffractometer Facility at the University of Hyderabad are gratefully acknowledged for computation and data collection work. RSR thanks the CSIR, New Delhi, for support under the scientist's pool scheme and NSK thanks the CSIR for a Senior Research Fellowship.

References

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