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Journal logoIUCrDATA
ISSN: 2414-3146

(E)-1-(4-Amino­phen­yl)-3-[4-(benz­yl­oxy)phen­yl]prop-2-en-1-one

aDepartment of Physics, Madras Christian College, Chennai 600 059, Tamilnadu, India, bDepartment of Chemistry, Madras Christian College, Chennai 600 059, Tamilnadu, India, cDepartment of Physics, Jerusalem College of Engineering, Chennai 100, Tamilnadu, India, and dPG and Research Department of Physics, Queen Mary's College, Chennai-4, Tamilnadu, India
*Correspondence e-mail: guqmc@yahoo.com

Edited by H. Stoeckli-Evans, University of Neuchâtel, Switzerland (Received 14 June 2016; accepted 26 August 2016; online 5 September 2016)

The title compound, C22H19NO2, crystallizes with two independent mol­ecules (A and B) in the asymmetric unit. The benz­yloxy ring in mol­ecule A is disordered over two sets of sites, with a refined occupancy ratio of 0.665 (6):0.335 (6). Both mol­ecules have an E conformation about the C=C bond of the prop-2-en-1-one unit. In the major component of mol­ecule A, the amino­benzene and benz­yloxy rings are inclined to the central benzene ring by 20.12 (16) and 36.2 (3)°, respectively, and by 55.6 (3)° to one another. In mol­ecule B, the corresponding dihedral angles are 23.65 (12), 10.24 (14) and 23.07 (14)°, respectively. In the crystal, the two mol­ecules are linked by an N—H⋯O hydrogen bond. These AB units are linked by N—H⋯π and C—H⋯π inter­actions, forming undulating sheets parallel to the ab plane.

3D view (loading...)
[Scheme 3D1]
Chemical scheme
[Scheme 1]

Structure description

Chalcones, members of the flavonoid family, constitute an important group of natural products owing to their wide range of pharmocological activities such as anti- inflammatory, anti­fungal, anti­viral, anti­microbial, anti­cancer and anti­tumor activities (Hamada & Sharshira, 2011[Hamada, N. M. & Sharshira, E. M. (2011). Molecules, 16, 2304-2312.]; Kumar et al., 2003[Kumar, S. K., Hager, E., Pettit, C., Gurulingappa, H., Davidson, N. E. & Khan, S. R. (2003). J. Med. Chem. 46, 2813-2815.]). Flavonoids are effectively exploited for their insecticidal and enzyme-inhibitory properties (Won et al., 2005[Won, S. J., Liu, C. T., Tsao, L. T., Weng, J. R., Ko, H. H., Wang, J. P. & Lin, C. N. (2005). Eur. J. Med. Chem. 40, 103-112.]; Churkin et al., 1982[Churkin, Y. D., Panfilova, L. V., Boreko, E. I., Timofeeva, M. M. & Votyakov, V. I. (1982). Pharm. Chem. J. 16, 103-105.]). In our efforts to study the biological activities of chalcone derivatives, we synthesized the title compound and report herein on its crystal structure.

The asymmetric unit of the title compound (Fig. 1[link]), contains two crystallographically independent mol­ecules (A and B). The benz­yloxy ring in mol­ecule A (O2/C16–C22) is disordered over two sets of sites. Both mol­ecules have an E conformation about the C=C bond of the prop-2-en-1-one unit. In the major component of mol­ecule A, the amino­benzene (C1–C6) and benz­yloxy (C17–C22) rings are inclined to the central benzene (C10–C15) ring by 20.12 (16) and 36.2 (3)°, respectively, and by 55.6 (3)° to one another. The corresponding dihedral angles in mol­ecule B differ quite considerably from those in mol­ecule A, with the amino­benzene (C23–C28) and benz­yloxy (C39–C44) rings inclined to the central benzene (C32–C37) ring by 23.65 (12) and 10.24 (14)°, and by only 23.07 (14)° to one another. The conformation of mol­ecule B is similar to that of the 4-hy­droxy­phenyl analogue, (E)-3-[4-(benz­yloxy)phen­yl]-1-(4-hy­droxy­phen­yl)prop-2-en-1-one (Ramkumar et al., 2013[Ramkumar, V., Anandhi, S., Kannan, P. & Gopalakrishnan, R. (2013). CrystEngComm, 15, 2438-2449.]) in which the corresponding dihedral angles are 24.7 (2), 9.6 (2) and 33.1 (2)°, respectively.

[Figure 1]
Figure 1
The mol­ecular structure of the two independent mol­ecules (A and B) of the title compound, with the atom labelling. Displacement ellipsoids drawn at the 30% probability level.

In the crystal, the two mol­ecules are linked by an N—H⋯O hydrogen bond (Table 1[link]). These AB units are linked by N—H⋯π and C—H⋯π inter­actions, forming undulating sheets parallel to the ab plane (Table 1[link] and Figs. 2[link] and 3[link]).

Table 1
Hydrogen-bond geometry (Å, °)

Cg1, Cg2 and Cg5 are the centroids of rings C1–C6, C10–C15 and C23–C28, respectively.

D—H⋯A D—H H⋯A DA D—H⋯A
N2—H2B⋯O1i 0.93 (4) 2.14 (4) 3.070 (5) 177 (3)
N1—H1ACg5ii 0.84 (5) 2.81 (4) 3.619 (5) 166 (4)
C2—H2⋯Cg1iii 0.93 2.97 3.699 (3) 136
C18—H18⋯Cg2iv 0.93 2.98 3.661 (7) 131
C40—H40⋯Cg5v 0.93 2.92 3.683 (3) 141
C16′—H16DCg2iv 0.97 2.87 3.757 (10) 152
Symmetry codes: (i) [x-{\script{1\over 2}}, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]; (ii) -x+1, -y+1, -z+2; (iii) [-x+{\script{3\over 2}}, y-{\script{1\over 2}}, -z+{\script{3\over 2}}]; (iv) x, y+1, z; (v) [-x+{\script{3\over 2}}, y-{\script{1\over 2}}, -z+{\script{5\over 2}}].
[Figure 2]
Figure 2
The crystal packing of the title compound, viewed along the c axis (major component of mol­ecule A blue, mol­ecule B red). The dashed lines indicate the hydrogen bonds and the N—H⋯π and C—H⋯π inter­actions (see Table 1[link]). For clarity, only H atoms (shown as balls) involved in these inter­actions have been included.
[Figure 3]
Figure 3
A partial view along the b axis, of the crystal packing of the title compound (major component of mol­ecule A blue, mol­ecule B red). The dashed lines indicate the hydrogen bonds and the N—H⋯π and C—H⋯π inter­actions (see Table 1[link]). For clarity, only H atoms (shown as balls) involved in these inter­actions have been included.

Synthesis and crystallization

In a 250 ml round-bottomed flask 120 ml of absolute alcohol was added to 4-amino­aceto­phenone (0.01 mol) and 4-benzyl­oxybenzaldehyde (0.01 mol), and the mixture stirred at room temperature. A 10% sodium hydroxide solution was added and the mixture stirred for a further 2 h. In order to precipitate the formed product the mixture was poured into 500 ml of ice-cold water. The precipitate was filtered, washed with distilled water and dried. It was purified by repeated recrystallization in absolute ethanol, giving yellow block-like crystals of the title compound (yield 97%).

Refinement

Crystal data, data collection and structure refinement details are summarized in Table 2[link]. The benz­yloxy ring in mol­ecule A is disordered over two sets of sites (O2/C16–C22 and O2′/C16′–C22′), with a refined occupancy ratio of 0.665 (6):0.335 (6).

Table 2
Experimental details

Crystal data
Chemical formula C22H19NO2
Mr 329.38
Crystal system, space group Monoclinic, P21/n
Temperature (K) 293
a, b, c (Å) 21.3428 (8), 5.7635 (2), 28.2870 (11)
β (°) 91.634 (1)
V3) 3478.1 (2)
Z 8
Radiation type Mo Kα
μ (mm−1) 0.08
Crystal size (mm) 0.30 × 0.25 × 0.20
 
Data collection
Diffractometer Bruker Kappa APEXII CCD
Absorption correction Multi-scan (SADABS; Bruker, 2004[Bruker (2004). APEX2, SAINT, XPREP and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.])
Tmin, Tmax 0.976, 0.984
No. of measured, independent and observed [I > 2σ(I)] reflections 36876, 6128, 3471
Rint 0.036
(sin θ/λ)max−1) 0.595
 
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.049, 0.191, 1.02
No. of reflections 6128
No. of parameters 541
No. of restraints 134
H-atom treatment H atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å−3) 0.16, −0.19
Computer programs: APEX2, SAINT and XPREP (Bruker, 2004[Bruker (2004). APEX2, SAINT, XPREP and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]), SIR92 (Altomare et al., 1993[Altomare, A., Cascarano, G., Giacovazzo, C. & Guagliardi, A. (1993). J. Appl. Cryst. 26, 343-350.]), SHELXL2014 (Sheldrick, 2015[Sheldrick, G. M. (2015). Acta Cryst. C71, 3-8.]), ORTEP-3 for Windows (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]) and Mercury (Macrae et al., 2008[Macrae, C. F., Bruno, I. J., Chisholm, J. A., Edgington, P. R., McCabe, P., Pidcock, E., Rodriguez-Monge, L., Taylor, R., van de Streek, J. & Wood, P. A. (2008). J. Appl. Cryst. 41, 466-470.]).

Structural data


Computing details top

Data collection: APEX2 (Bruker, 2004); cell refinement: APEX2/SAINT (Bruker, 2004); data reduction: SAINT/XPREP (Bruker, 2004); program(s) used to solve structure: SIR92 (Altomare et al., 1993); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012) and Mercury (Macrae et al., 2008); software used to prepare material for publication: SHELXL2014 (Sheldrick, 2015).

(E)-1-(4-Aminophenyl)-3-[4-(benzyloxy)phenyl]prop-2-en-1-one top
Crystal data top
C22H19NO2F(000) = 1392
Mr = 329.38Dx = 1.258 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
a = 21.3428 (8) ÅCell parameters from 8554 reflections
b = 5.7635 (2) Åθ = 2.4–21.9°
c = 28.2870 (11) ŵ = 0.08 mm1
β = 91.634 (1)°T = 293 K
V = 3478.1 (2) Å3Block, yellow
Z = 80.30 × 0.25 × 0.20 mm
Data collection top
Bruker Kappa APEXII CCD
diffractometer
6128 independent reflections
Radiation source: fine-focus sealed tube3471 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.036
ω and φ scanθmax = 25.0°, θmin = 2.4°
Absorption correction: multi-scan
(SADABS; Bruker, 2004)
h = 2524
Tmin = 0.976, Tmax = 0.984k = 66
36876 measured reflectionsl = 2633
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: mixed
R[F2 > 2σ(F2)] = 0.049H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.191 w = 1/[σ2(Fo2) + (0.0963P)2 + 0.9188P]
where P = (Fo2 + 2Fc2)/3
S = 1.02(Δ/σ)max = 0.004
6128 reflectionsΔρmax = 0.16 e Å3
541 parametersΔρmin = 0.19 e Å3
134 restraintsExtinction correction: SHELXL2014 (Sheldrick, 2015), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0029 (7)
Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
C10.66578 (15)0.2791 (6)0.76246 (11)0.0842 (9)
C20.71650 (15)0.3689 (6)0.78799 (11)0.0846 (9)
H20.73460.50740.77840.102*
C30.74027 (13)0.2569 (6)0.82699 (11)0.0761 (8)
H30.77440.32100.84340.091*
C40.71491 (12)0.0492 (5)0.84300 (10)0.0694 (8)
C50.66439 (14)0.0399 (6)0.81634 (11)0.0840 (9)
H50.64660.18010.82520.101*
C60.64038 (15)0.0739 (6)0.77743 (12)0.0918 (10)
H60.60620.01110.76080.110*
C70.74135 (14)0.0647 (5)0.88568 (11)0.0742 (8)
C80.70887 (13)0.2667 (5)0.90498 (11)0.0770 (8)
H80.67960.34320.88560.092*
C90.71895 (13)0.3453 (5)0.94832 (11)0.0746 (8)
H90.74960.26800.96620.089*
C100.68838 (13)0.5370 (5)0.97165 (11)0.0712 (8)
C110.64444 (15)0.6768 (6)0.94886 (12)0.0862 (9)
H110.63480.65100.91700.103*
C120.61492 (17)0.8505 (7)0.97172 (13)0.0977 (11)
H120.58560.94170.95540.117*
C130.62783 (15)0.8934 (6)1.01877 (13)0.0855 (9)
C140.67269 (15)0.7612 (6)1.04260 (12)0.0879 (9)
H140.68300.79061.07420.105*
C150.70157 (14)0.5862 (6)1.01876 (12)0.0838 (9)
H150.73140.49641.03500.101*
C230.40931 (11)1.0076 (5)1.39037 (9)0.0613 (7)
C240.43961 (13)1.2218 (5)1.39056 (10)0.0702 (8)
H240.42901.33311.41270.084*
C250.48466 (12)1.2709 (4)1.35868 (9)0.0642 (7)
H250.50421.41521.35970.077*
C260.50210 (11)1.1101 (4)1.32472 (8)0.0536 (6)
C270.47235 (11)0.8958 (5)1.32505 (9)0.0595 (7)
H270.48360.78321.30330.071*
C280.42673 (11)0.8464 (5)1.35673 (9)0.0620 (7)
H280.40710.70231.35570.074*
C290.55081 (12)1.1757 (5)1.29130 (9)0.0611 (7)
C300.58160 (12)0.9971 (4)1.26320 (8)0.0590 (7)
H300.56410.84951.26100.071*
C310.63412 (12)1.0435 (5)1.24088 (8)0.0596 (7)
H310.64901.19461.24380.071*
C320.67115 (11)0.8876 (4)1.21254 (8)0.0541 (6)
C330.73159 (12)0.9480 (5)1.20084 (9)0.0628 (7)
H330.74791.08871.21160.075*
C340.76849 (12)0.8051 (5)1.17363 (8)0.0621 (7)
H340.80920.84831.16670.075*
C350.74420 (12)0.5989 (5)1.15706 (8)0.0585 (6)
C360.68406 (13)0.5352 (5)1.16836 (10)0.0705 (8)
H360.66750.39561.15720.085*
C370.64855 (12)0.6769 (5)1.19594 (9)0.0650 (7)
H370.60840.63031.20360.078*
C380.83712 (13)0.4868 (6)1.11791 (10)0.0782 (9)
H38A0.86320.47291.14640.094*
H38B0.84150.64341.10580.094*
C390.85833 (12)0.3169 (5)1.08190 (8)0.0635 (7)
C400.91657 (14)0.3446 (7)1.06354 (11)0.0968 (11)
H400.94220.46531.07420.116*
C410.93766 (16)0.1951 (8)1.02936 (13)0.1127 (13)
H410.97710.21691.01700.135*
C420.90094 (17)0.0153 (6)1.01360 (11)0.0917 (10)
H420.91550.08720.99100.110*
C430.84347 (17)0.0118 (6)1.03113 (11)0.0911 (10)
H430.81780.13181.02010.109*
C440.82232 (15)0.1370 (6)1.06529 (10)0.0816 (9)
H440.78270.11451.07730.098*
O10.78887 (10)0.0107 (4)0.90580 (8)0.0962 (7)
O30.56699 (10)1.3799 (4)1.28826 (8)0.0923 (7)
O40.77438 (8)0.4456 (3)1.12854 (7)0.0783 (6)
N10.6416 (2)0.3944 (9)0.72373 (14)0.1351 (15)
N20.36548 (13)0.9551 (7)1.42293 (11)0.0857 (8)
O20.5882 (2)1.0498 (8)1.03545 (17)0.0858 (16)0.665 (6)
C160.5999 (3)1.1013 (11)1.0832 (2)0.0804 (17)0.665 (6)
H16A0.64241.15911.08750.097*0.665 (6)
H16B0.59590.96171.10200.097*0.665 (6)
C170.5551 (3)1.2776 (12)1.0990 (3)0.0810 (19)0.665 (6)
C180.5384 (3)1.4543 (16)1.0683 (2)0.0926 (18)0.665 (6)
H180.55361.45421.03780.111*0.665 (6)
C190.4992 (4)1.6319 (15)1.0822 (4)0.113 (3)0.665 (6)
H190.48871.74991.06100.136*0.665 (6)
C200.4758 (5)1.636 (2)1.1268 (4)0.116 (3)0.665 (6)
H200.45121.76021.13630.139*0.665 (6)
C210.4889 (4)1.4579 (19)1.1573 (3)0.113 (3)0.665 (6)
H210.47181.45521.18720.136*0.665 (6)
C220.5281 (5)1.2815 (18)1.1432 (3)0.102 (3)0.665 (6)
H220.53681.16041.16410.123*0.665 (6)
O2'0.6126 (5)1.0846 (17)1.0544 (4)0.098 (4)0.335 (6)
C16'0.5607 (4)1.2296 (18)1.0416 (3)0.077 (3)0.335 (6)
H16C0.52881.13851.02510.093*0.335 (6)
H16D0.57431.35091.02040.093*0.335 (6)
C17'0.5334 (7)1.338 (3)1.0855 (5)0.072 (3)0.335 (6)
C18'0.5086 (10)1.551 (3)1.0777 (5)0.090 (4)0.335 (6)
H18'0.51331.62351.04870.108*0.335 (6)
C19'0.4767 (11)1.660 (4)1.1125 (5)0.090 (5)0.335 (6)
H19'0.45741.80241.10630.108*0.335 (6)
C20'0.4730 (6)1.560 (2)1.1568 (5)0.078 (3)0.335 (6)
H20'0.45401.63881.18130.094*0.335 (6)
C21'0.4980 (6)1.341 (2)1.1640 (5)0.076 (3)0.335 (6)
H21'0.49341.26531.19280.091*0.335 (6)
C22'0.5295 (8)1.236 (3)1.1285 (6)0.076 (4)0.335 (6)
H22'0.54841.09241.13380.091*0.335 (6)
H2B0.3414 (18)0.822 (7)1.4189 (12)0.120 (14)*
H2A0.3524 (16)1.065 (6)1.4385 (11)0.094 (12)*
H1B0.663 (2)0.508 (8)0.7123 (16)0.16 (2)*
H1A0.614 (2)0.334 (8)0.7064 (16)0.149 (19)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.077 (2)0.094 (2)0.081 (2)0.0092 (19)0.0012 (17)0.0071 (18)
C20.083 (2)0.077 (2)0.094 (2)0.0092 (17)0.0007 (18)0.0057 (18)
C30.0641 (17)0.078 (2)0.086 (2)0.0053 (16)0.0022 (15)0.0134 (17)
C40.0538 (15)0.084 (2)0.0705 (17)0.0048 (15)0.0055 (13)0.0057 (16)
C50.0740 (19)0.091 (2)0.087 (2)0.0158 (17)0.0017 (17)0.0099 (18)
C60.079 (2)0.109 (3)0.087 (2)0.025 (2)0.0114 (17)0.013 (2)
C70.0586 (17)0.082 (2)0.082 (2)0.0061 (16)0.0072 (15)0.0090 (17)
C80.0682 (18)0.086 (2)0.077 (2)0.0092 (17)0.0022 (15)0.0050 (17)
C90.0534 (15)0.085 (2)0.086 (2)0.0113 (15)0.0024 (14)0.0078 (17)
C100.0564 (16)0.077 (2)0.080 (2)0.0132 (15)0.0011 (14)0.0099 (16)
C110.090 (2)0.087 (2)0.082 (2)0.0034 (19)0.0016 (18)0.0185 (19)
C120.103 (3)0.095 (3)0.094 (3)0.009 (2)0.004 (2)0.038 (2)
C130.078 (2)0.071 (2)0.108 (3)0.0054 (19)0.0155 (19)0.017 (2)
C140.080 (2)0.095 (2)0.089 (2)0.0084 (19)0.0006 (17)0.0047 (19)
C150.0643 (18)0.093 (2)0.093 (2)0.0051 (17)0.0096 (16)0.0028 (19)
C230.0545 (15)0.0652 (18)0.0647 (15)0.0071 (14)0.0103 (13)0.0026 (13)
C240.0787 (18)0.0602 (18)0.0727 (17)0.0078 (15)0.0204 (14)0.0115 (14)
C250.0714 (17)0.0479 (15)0.0739 (17)0.0054 (13)0.0139 (14)0.0048 (13)
C260.0561 (14)0.0448 (15)0.0601 (14)0.0094 (12)0.0074 (11)0.0012 (12)
C270.0592 (15)0.0558 (16)0.0638 (15)0.0068 (13)0.0076 (12)0.0071 (13)
C280.0554 (15)0.0574 (17)0.0733 (16)0.0000 (13)0.0052 (13)0.0026 (14)
C290.0667 (16)0.0485 (17)0.0685 (16)0.0057 (13)0.0107 (13)0.0042 (13)
C300.0637 (15)0.0500 (15)0.0639 (15)0.0053 (12)0.0119 (13)0.0040 (12)
C310.0624 (16)0.0576 (16)0.0590 (14)0.0040 (13)0.0077 (12)0.0010 (12)
C320.0542 (14)0.0547 (16)0.0539 (13)0.0027 (12)0.0076 (11)0.0037 (12)
C330.0611 (16)0.0611 (17)0.0667 (15)0.0035 (14)0.0078 (13)0.0041 (13)
C340.0511 (14)0.0730 (19)0.0627 (15)0.0017 (14)0.0106 (12)0.0022 (14)
C350.0590 (15)0.0612 (17)0.0558 (14)0.0055 (14)0.0124 (12)0.0047 (13)
C360.0688 (17)0.0647 (18)0.0789 (18)0.0086 (15)0.0198 (15)0.0128 (14)
C370.0549 (15)0.0676 (18)0.0736 (17)0.0047 (14)0.0195 (13)0.0070 (14)
C380.0608 (17)0.099 (2)0.0758 (18)0.0015 (16)0.0149 (14)0.0189 (16)
C390.0597 (16)0.0779 (19)0.0533 (14)0.0109 (15)0.0064 (12)0.0071 (13)
C400.0656 (19)0.130 (3)0.095 (2)0.0030 (19)0.0168 (17)0.042 (2)
C410.072 (2)0.153 (4)0.115 (3)0.006 (2)0.0342 (19)0.041 (3)
C420.098 (3)0.098 (3)0.080 (2)0.016 (2)0.0201 (19)0.0204 (18)
C430.101 (2)0.079 (2)0.095 (2)0.0058 (19)0.0249 (19)0.0207 (18)
C440.079 (2)0.083 (2)0.084 (2)0.0018 (18)0.0268 (16)0.0106 (18)
O10.0700 (13)0.1152 (18)0.1026 (16)0.0058 (13)0.0122 (12)0.0056 (13)
O30.1107 (16)0.0543 (13)0.1147 (16)0.0020 (12)0.0530 (13)0.0015 (11)
O40.0680 (12)0.0818 (13)0.0867 (13)0.0025 (10)0.0275 (10)0.0225 (11)
N10.130 (3)0.150 (4)0.123 (3)0.046 (3)0.045 (2)0.058 (3)
N20.0801 (18)0.085 (2)0.0938 (19)0.0027 (17)0.0346 (15)0.0080 (17)
O20.090 (3)0.080 (3)0.086 (3)0.017 (3)0.018 (2)0.0083 (18)
C160.079 (3)0.077 (3)0.084 (3)0.004 (3)0.014 (3)0.014 (3)
C170.067 (3)0.073 (3)0.102 (4)0.006 (2)0.009 (3)0.022 (2)
C180.070 (3)0.083 (4)0.126 (4)0.011 (3)0.012 (3)0.008 (3)
C190.084 (4)0.086 (5)0.171 (6)0.016 (4)0.037 (4)0.002 (4)
C200.068 (5)0.116 (6)0.165 (7)0.006 (4)0.028 (5)0.019 (5)
C210.093 (5)0.107 (6)0.139 (6)0.012 (4)0.015 (4)0.035 (4)
C220.092 (5)0.112 (5)0.103 (4)0.004 (3)0.001 (4)0.027 (3)
O2'0.066 (5)0.100 (7)0.129 (11)0.008 (4)0.003 (5)0.024 (7)
C16'0.069 (4)0.078 (6)0.084 (5)0.005 (4)0.004 (3)0.001 (4)
C17'0.068 (7)0.063 (6)0.087 (5)0.017 (5)0.006 (4)0.004 (4)
C18'0.101 (10)0.068 (6)0.102 (6)0.003 (5)0.008 (5)0.006 (4)
C19'0.099 (11)0.079 (7)0.091 (5)0.016 (7)0.006 (5)0.004 (4)
C20'0.070 (7)0.071 (6)0.092 (5)0.010 (5)0.013 (4)0.005 (4)
C21'0.069 (6)0.075 (6)0.082 (5)0.015 (5)0.003 (4)0.000 (4)
C22'0.074 (7)0.064 (6)0.091 (5)0.000 (5)0.014 (5)0.002 (4)
Geometric parameters (Å, º) top
C1—N11.370 (5)C35—O41.370 (3)
C1—C61.373 (4)C35—C361.381 (4)
C1—C21.384 (4)C36—C371.373 (3)
C2—C31.363 (4)C36—H360.9300
C2—H20.9300C37—H370.9300
C3—C41.395 (4)C38—O41.401 (3)
C3—H30.9300C38—C391.493 (4)
C4—C51.396 (4)C38—H38A0.9700
C4—C71.472 (4)C38—H38B0.9700
C5—C61.368 (4)C39—C441.366 (4)
C5—H50.9300C39—C401.370 (4)
C6—H60.9300C40—C411.380 (4)
C7—O11.228 (3)C40—H400.9300
C7—C81.468 (4)C41—C421.366 (5)
C8—C91.319 (4)C41—H410.9300
C8—H80.9300C42—C431.345 (4)
C9—C101.451 (4)C42—H420.9300
C9—H90.9300C43—C441.378 (4)
C10—C111.382 (4)C43—H430.9300
C10—C151.383 (4)C44—H440.9300
C11—C121.357 (5)N1—H1B0.87 (5)
C11—H110.9300N1—H1A0.84 (5)
C12—C131.374 (5)N2—H2B0.93 (4)
C12—H120.9300N2—H2A0.83 (3)
C13—O21.332 (5)O2—C161.397 (7)
C13—C141.384 (4)C16—C171.474 (8)
C13—O2'1.534 (11)C16—H16A0.9700
C14—C151.370 (4)C16—H16B0.9700
C14—H140.9300C17—C181.379 (8)
C15—H150.9300C17—C221.393 (8)
C23—N21.365 (4)C18—C191.386 (8)
C23—C281.388 (3)C18—H180.9300
C23—C241.394 (4)C19—C201.371 (9)
C24—C251.367 (4)C19—H190.9300
C24—H240.9300C20—C211.367 (11)
C25—C261.393 (3)C20—H200.9300
C25—H250.9300C21—C221.382 (10)
C26—C271.389 (4)C21—H210.9300
C26—C291.475 (3)C22—H220.9300
C27—C281.372 (3)O2'—C16'1.425 (11)
C27—H270.9300C16'—C17'1.523 (15)
C28—H280.9300C16'—H16C0.9700
C29—O31.230 (3)C16'—H16D0.9700
C29—C301.467 (3)C17'—C18'1.352 (14)
C30—C311.329 (3)C17'—C22'1.356 (13)
C30—H300.9300C18'—C19'1.366 (14)
C31—C321.453 (3)C18'—H18'0.9300
C31—H310.9300C19'—C20'1.385 (13)
C32—C371.383 (4)C19'—H19'0.9300
C32—C331.385 (3)C20'—C21'1.387 (13)
C33—C341.388 (3)C20'—H20'0.9300
C33—H330.9300C21'—C22'1.365 (12)
C34—C351.373 (4)C21'—H21'0.9300
C34—H340.9300C22'—H22'0.9300
N1—C1—C6121.4 (3)C37—C36—H36119.8
N1—C1—C2120.5 (4)C35—C36—H36119.8
C6—C1—C2118.1 (3)C36—C37—C32121.5 (2)
C3—C2—C1120.8 (3)C36—C37—H37119.3
C3—C2—H2119.6C32—C37—H37119.3
C1—C2—H2119.6O4—C38—C39110.2 (2)
C2—C3—C4122.0 (3)O4—C38—H38A109.6
C2—C3—H3119.0C39—C38—H38A109.6
C4—C3—H3119.0O4—C38—H38B109.6
C3—C4—C5116.2 (3)C39—C38—H38B109.6
C3—C4—C7120.4 (3)H38A—C38—H38B108.1
C5—C4—C7123.5 (3)C44—C39—C40117.8 (3)
C6—C5—C4121.6 (3)C44—C39—C38123.6 (2)
C6—C5—H5119.2C40—C39—C38118.6 (3)
C4—C5—H5119.2C39—C40—C41120.7 (3)
C5—C6—C1121.3 (3)C39—C40—H40119.7
C5—C6—H6119.4C41—C40—H40119.7
C1—C6—H6119.4C42—C41—C40120.4 (3)
O1—C7—C8120.1 (3)C42—C41—H41119.8
O1—C7—C4121.0 (3)C40—C41—H41119.8
C8—C7—C4119.0 (3)C43—C42—C41119.2 (3)
C9—C8—C7123.5 (3)C43—C42—H42120.4
C9—C8—H8118.2C41—C42—H42120.4
C7—C8—H8118.2C42—C43—C44120.4 (3)
C8—C9—C10128.4 (3)C42—C43—H43119.8
C8—C9—H9115.8C44—C43—H43119.8
C10—C9—H9115.8C39—C44—C43121.4 (3)
C11—C10—C15116.5 (3)C39—C44—H44119.3
C11—C10—C9122.6 (3)C43—C44—H44119.3
C15—C10—C9120.8 (3)C35—O4—C38119.0 (2)
C12—C11—C10121.7 (3)C1—N1—H1B118 (3)
C12—C11—H11119.1C1—N1—H1A121 (3)
C10—C11—H11119.1H1B—N1—H1A118 (4)
C11—C12—C13120.8 (3)C23—N2—H2B119 (2)
C11—C12—H12119.6C23—N2—H2A116 (2)
C13—C12—H12119.6H2B—N2—H2A120 (3)
O2—C13—C12110.7 (4)C13—O2—C16112.8 (4)
O2—C13—C14129.6 (4)O2—C16—C17109.8 (5)
C12—C13—C14119.3 (3)O2—C16—H16A109.7
C12—C13—O2'136.4 (5)C17—C16—H16A109.7
C14—C13—O2'103.5 (5)O2—C16—H16B109.7
C15—C14—C13118.7 (3)C17—C16—H16B109.7
C15—C14—H14120.6H16A—C16—H16B108.2
C13—C14—H14120.6C18—C17—C22116.6 (7)
C14—C15—C10122.9 (3)C18—C17—C16118.5 (7)
C14—C15—H15118.6C22—C17—C16124.9 (9)
C10—C15—H15118.6C17—C18—C19120.9 (7)
N2—C23—C28121.1 (3)C17—C18—H18119.6
N2—C23—C24121.4 (3)C19—C18—H18119.6
C28—C23—C24117.5 (2)C20—C19—C18121.0 (9)
C25—C24—C23121.1 (2)C20—C19—H19119.5
C25—C24—H24119.5C18—C19—H19119.5
C23—C24—H24119.5C21—C20—C19119.6 (10)
C24—C25—C26121.6 (3)C21—C20—H20120.2
C24—C25—H25119.2C19—C20—H20120.2
C26—C25—H25119.2C20—C21—C22119.1 (9)
C27—C26—C25117.1 (2)C20—C21—H21120.5
C27—C26—C29124.3 (2)C22—C21—H21120.5
C25—C26—C29118.6 (2)C21—C22—C17122.7 (9)
C28—C27—C26121.4 (2)C21—C22—H22118.6
C28—C27—H27119.3C17—C22—H22118.6
C26—C27—H27119.3C16'—O2'—C13115.6 (9)
C27—C28—C23121.2 (2)O2'—C16'—C17'110.3 (10)
C27—C28—H28119.4O2'—C16'—H16C109.6
C23—C28—H28119.4C17'—C16'—H16C109.6
O3—C29—C30120.2 (2)O2'—C16'—H16D109.6
O3—C29—C26119.6 (2)C17'—C16'—H16D109.6
C30—C29—C26120.1 (2)H16C—C16'—H16D108.1
C31—C30—C29120.9 (2)C18'—C17'—C22'120.5 (13)
C31—C30—H30119.6C18'—C17'—C16'113.4 (14)
C29—C30—H30119.6C22'—C17'—C16'126.0 (15)
C30—C31—C32128.1 (3)C17'—C18'—C19'120.1 (15)
C30—C31—H31115.9C17'—C18'—H18'119.9
C32—C31—H31115.9C19'—C18'—H18'119.9
C37—C32—C33117.2 (2)C18'—C19'—C20'120.1 (16)
C37—C32—C31122.7 (2)C18'—C19'—H19'120.0
C33—C32—C31120.1 (2)C20'—C19'—H19'120.0
C32—C33—C34122.0 (3)C19'—C20'—C21'118.9 (14)
C32—C33—H33119.0C19'—C20'—H20'120.6
C34—C33—H33119.0C21'—C20'—H20'120.6
C35—C34—C33119.2 (2)C22'—C21'—C20'119.4 (13)
C35—C34—H34120.4C22'—C21'—H21'120.3
C33—C34—H34120.4C20'—C21'—H21'120.3
O4—C35—C34125.4 (2)C17'—C22'—C21'120.7 (14)
O4—C35—C36114.9 (2)C17'—C22'—H22'119.6
C34—C35—C36119.7 (2)C21'—C22'—H22'119.6
C37—C36—C35120.3 (3)
N1—C1—C2—C3179.0 (4)C37—C32—C33—C340.0 (4)
C6—C1—C2—C30.3 (5)C31—C32—C33—C34179.6 (2)
C1—C2—C3—C40.2 (5)C32—C33—C34—C351.1 (4)
C2—C3—C4—C51.1 (4)C33—C34—C35—O4177.5 (2)
C2—C3—C4—C7179.1 (3)C33—C34—C35—C361.1 (4)
C3—C4—C5—C61.6 (4)O4—C35—C36—C37178.7 (2)
C7—C4—C5—C6178.6 (3)C34—C35—C36—C370.1 (4)
C4—C5—C6—C11.2 (5)C35—C36—C37—C321.0 (4)
N1—C1—C6—C5179.5 (4)C33—C32—C37—C361.1 (4)
C2—C1—C6—C50.2 (5)C31—C32—C37—C36178.6 (2)
C3—C4—C7—O15.6 (4)O4—C38—C39—C445.0 (4)
C5—C4—C7—O1174.2 (3)O4—C38—C39—C40173.5 (3)
C3—C4—C7—C8172.4 (2)C44—C39—C40—C410.1 (5)
C5—C4—C7—C87.8 (4)C38—C39—C40—C41178.5 (3)
O1—C7—C8—C915.3 (4)C39—C40—C41—C420.7 (6)
C4—C7—C8—C9162.7 (3)C40—C41—C42—C431.3 (6)
C7—C8—C9—C10177.7 (3)C41—C42—C43—C441.3 (5)
C8—C9—C10—C113.7 (5)C40—C39—C44—C430.2 (5)
C8—C9—C10—C15175.3 (3)C38—C39—C44—C43178.3 (3)
C15—C10—C11—C121.1 (4)C42—C43—C44—C390.8 (5)
C9—C10—C11—C12177.9 (3)C34—C35—O4—C385.8 (4)
C10—C11—C12—C130.1 (5)C36—C35—O4—C38175.5 (2)
C11—C12—C13—O2171.9 (4)C39—C38—O4—C35173.0 (2)
C11—C12—C13—C141.7 (5)C12—C13—O2—C16179.3 (5)
C11—C12—C13—O2'169.7 (7)C14—C13—O2—C167.9 (7)
O2—C13—C14—C15170.3 (4)C13—O2—C16—C17179.1 (6)
C12—C13—C14—C152.0 (5)O2—C16—C17—C1838.3 (8)
O2'—C13—C14—C15173.5 (5)O2—C16—C17—C22142.2 (7)
C13—C14—C15—C100.7 (5)C22—C17—C18—C193.3 (9)
C11—C10—C15—C140.8 (5)C16—C17—C18—C19176.2 (7)
C9—C10—C15—C14178.2 (3)C17—C18—C19—C200.3 (11)
N2—C23—C24—C25178.2 (3)C18—C19—C20—C212.9 (13)
C28—C23—C24—C250.2 (4)C19—C20—C21—C223.0 (13)
C23—C24—C25—C260.1 (4)C20—C21—C22—C170.1 (13)
C24—C25—C26—C270.9 (4)C18—C17—C22—C213.2 (11)
C24—C25—C26—C29179.6 (2)C16—C17—C22—C21176.2 (8)
C25—C26—C27—C281.5 (4)C12—C13—O2'—C16'19.2 (13)
C29—C26—C27—C28179.1 (2)C14—C13—O2'—C16'171.5 (8)
C26—C27—C28—C231.2 (4)C13—O2'—C16'—C17'156.4 (9)
N2—C23—C28—C27177.7 (3)O2'—C16'—C17'—C18'148.4 (13)
C24—C23—C28—C270.4 (4)O2'—C16'—C17'—C22'35.4 (17)
C27—C26—C29—O3167.8 (3)C22'—C17'—C18'—C19'3 (2)
C25—C26—C29—O312.8 (4)C16'—C17'—C18'—C19'173.3 (15)
C27—C26—C29—C3014.6 (4)C17'—C18'—C19'—C20'4 (3)
C25—C26—C29—C30164.7 (2)C18'—C19'—C20'—C21'5 (2)
O3—C29—C30—C3112.2 (4)C19'—C20'—C21'—C22'4.6 (18)
C26—C29—C30—C31165.3 (2)C18'—C17'—C22'—C21'3 (2)
C29—C30—C31—C32178.7 (2)C16'—C17'—C22'—C21'173.0 (13)
C30—C31—C32—C3715.2 (4)C20'—C21'—C22'—C17'4 (2)
C30—C31—C32—C33165.2 (3)
Hydrogen-bond geometry (Å, º) top
Cg1, Cg2 and Cg5 are the centroids of rings C1–C6, C10–C15 and C23–C28, respectively.
D—H···AD—HH···AD···AD—H···A
N2—H2B···O1i0.93 (4)2.14 (4)3.070 (5)177 (3)
N1—H1A···Cg5ii0.84 (5)2.81 (4)3.619 (5)166 (4)
C2—H2···Cg1iii0.932.973.699 (3)136
C18—H18···Cg2iv0.932.983.661 (7)131
C40—H40···Cg5v0.932.923.683 (3)141
C16—H16D···Cg2iv0.972.873.757 (10)152
Symmetry codes: (i) x1/2, y+1/2, z+1/2; (ii) x+1, y+1, z+2; (iii) x+3/2, y1/2, z+3/2; (iv) x, y+1, z; (v) x+3/2, y1/2, z+5/2.
 

Acknowledgements

The authors thank the SAIF, IIT, Madras, for the X-ray data-collection facility.

References

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