4-(2-Nitro­benz­yl)-3-phenyl-3,4-di­hydro-2H-1,4-benzoxazin-2-ol

Chouguiat, L.; Boulcina, R.; Bouacida, S.; Merazig, H.; Debache, A.

doi:10.1107/S1600536814015645

organic compounds

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ISSN: 2056-9890

Volume 70| Part 8| August 2014| Pages o863-o864

doi:10.1107/S1600536814015645

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4-(2-Nitrobenzyl)-3-phenyl-3,4-dihydro-2H-1,4-benzoxazin-2-ol

Louisa Chouguiat,^a Raouf Boulcina,^a Sofiane Bouacida,^b,^c ^* Hocine Merazig ^b and Abdelmadjid Debache ^a

^aLaboratoire de Synthèse des Molécules d'Intérêts Biologiques, Département de Chimie, Faculté des Sciences Exactes, Université de Constantine 1, 25000 Constantine, Algeria, ^bUnité de Recherche de Chimie de l'Environnement et Moléculaire Structurale, CHEMS, Université Constantine 1, 25000 , Algeria, and ^cDépartement Sciences de la Matière, Faculté des Sciences Exactes et Sciences de la Nature et de la Vie, Université Oum El Bouaghi 04000, Algeria
^*Correspondence e-mail: bouacida_sofiane@yahoo.fr

Edited by O. Büyükgüngör, Ondokuz Mayıs University, Turkey (Received 1 June 2014; accepted 4 July 2014; online 11 July 2014)

The title compound, C₂₁H₁₈N₂O₄, crystallizes with two independent molecules (A and B) in the asymmetric unit. In both molecules the oxazine ring has an envelope conformation with the hydroxyl-substituted C atom as the flap. The nitrobenzyl ring and the phenyl ring are almost normal to the mean plane of the benzooxazine ring system with dihdral angles of 85.72 (15) and 82.69 (15)°, respectively, in molecule A, and 85.79 (15) and 87.72 (15)°, respectively, in molecule B. The main difference in the conformation of the two molecules concerns the dihedral angle between the nitrobenzyl ring and the phenyl ring, viz. 79.67 (18) in molecule A and 71.13 (18)° in molecule B. In the crystal, the A and B molecules are linked by an O—H⋯O hydrogen bond. These units are then linked via C—H⋯O hydrogen bonds, forming sheets lying parallel to (010). Further C—H⋯O hydrogen bonds link the sheets to form a three-dimensional network. There are also O—H⋯π and C—H⋯π interactions present, reinforcing the three-dimensional structure.

Keywords: crystal structure.

CCDC reference: 1012140

Related literature

For the preparation and applications of similar structures, see: Ozden et al. (1992 ); Hartenstein & Sicker (1994 ); Ilas et al. (2005 ); Touzeau et al. (2003 ); Torisu et al. (2004 ); Largeron et al. (1999 ).

Experimental

Crystal data

C₂₁H₁₈N₂O₄
M_r = 362.37
Orthorhombic, P n a 2₁
a = 12.7332 (14) Å
b = 14.2777 (14) Å
c = 19.003 (2) Å
V = 3454.8 (6) Å³
Z = 8
Mo Kα radiation
μ = 0.10 mm⁻¹
T = 150 K
0.13 × 0.05 × 0.03 mm

Data collection

Bruker APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 2002 ) T_min = 0.860, T_max = 1.000
19156 measured reflections
3161 independent reflections
4907 reflections with I > 2σ(I)
R_int = 0.052

Refinement

R[F² > 2σ(F²)] = 0.043
wR(F²) = 0.114
S = 1.04
3161 reflections
489 parameters
1 restraint
H-atom parameters constrained
Δρ_max = 0.71 e Å⁻³
Δρ_min = −0.26 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 and Cg2 are the controids of the C10A–C15A and C10B–C15B rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2A—H2A⋯O1B	0.82	2.06	2.843 (4)	161
C6B—H6B⋯O21Aⁱ	0.93	2.40	3.175 (5)	141
C8B—H8B⋯O1Aⁱⁱ	0.98	2.34	3.234 (4)	151
C14A—H14A⋯O2Aⁱⁱⁱ	0.93	2.57	3.177 (5)	123
C19A—H19A⋯O21B^iv	0.93	2.45	3.134 (4)	131
C19B—H19B⋯O22A^v	0.93	2.47	3.057 (5)	121
O2B—H2B⋯Cg1ⁱⁱ	0.82	2.69	3.484 (3)	164
C18A—H18A⋯Cg2^iv	0.93	2.83	3.564 (4)	137
C18B—H18B⋯Cg1^v	0.93	2.94	3.601 (4)	130
Symmetry codes: (i) $[x-{\script{1\over 2}}, -y+{\script{1\over 2}}, z+1]$ ; (ii) $[x-{\script{1\over 2}}, -y+{\script{1\over 2}}, z]$ ; (iii) $[x+{\script{1\over 2}}, -y+{\script{1\over 2}}, z]$ ; (iv) $[-x+{\script{1\over 2}}, y+{\script{1\over 2}}, z-{\script{1\over 2}}]$ ; (v) $[-x+{\script{1\over 2}}, y+{\script{1\over 2}}, z+{\script{1\over 2}}]$ .

Data collection: APEX2 (Bruker, 2011 ); cell refinement: SAINT (Bruker, 2011); data reduction: SAINT; program(s) used to solve structure: SIR2002 (Burla et al., 2003 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ) and DIAMOND (Brandenburg & Berndt, 2001 ); software used to prepare material for publication: WinGX publication routines (Farrugia, 2012).

Supporting information

CCDC reference: 1012140

Crystal structure: contains datablock I. DOI: 10.1107/S1600536814015645/bq2396sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536814015645/bq2396Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536814015645/bq2396Isup3.cml

checkCIF report

Comment top

Numerous natural and synthetic substances that have the core "1,4-benzoxazine" have been used in different fields of medicine. The 1,4-benzoxazine structure is an integral part of several naturally occurring substances. For example, various glycosides of the 2-hydroxy-2H-1,4-benzoxazine skeletons have been found to occur in gramineous plants such as maize, wheat, rye, and rice, and have been suggested to act as plant resistance factors against microbial diseases and insects (Ozden et al., 1992; Hartenstein & Sicker, 1994). Moreover, 3,4-Dihydro-2H-1,4-benzoxazines have received a great deal of attention due to their wide range of biological and therapeutical properties (Ilas et al., 2005). For example they have been investigated as antihypertensive agents (Touzeau et al., 2003), neuroprotective antioxidants (Largeron et al., 1999) and prostaglandin D 2 receptor antagonists (Torisu et al., 2004). Herein, we report our results about the synthesis and the crystallographic study of 4-(2-nitrobenzyl)-3-phenyl-3,4-dihydro-2H-benzo[b][1,4]oxazin-2-ol, (I). The molecular geometry and the atom-numbering scheme of asymetric unit are shown in Fig. 1. The asymetric unit contents two molecule of (I). The crystal packing can be described as alternating connected layers parallel to the (001) plane along the c axis (Fig. 2) It is stabilized by intra et intermolecular O—H···O and C—H···O hydrogen bond and O—H···π interactions (Table 1; Fig. 2). These interactions link the molecules within the layers and also link the layers together and reinforcing the cohesion of the structure.

Related literature top

For the preparation and applications of similar structures, see: Ozden et al. (1992); Hartenstein & Sicker (1994); Ilas et al. (2005); Touzeau et al. (2003); Torisu et al. (2004); Largeron et al. (1999).

Experimental top

A mixture of 4-methyl-2-(2-nitrobenzylamino)phenol (1 mmol), boronic acid (1 mmol) and glyoxal (1 mmol) in methanol (5 ml) was stirred at room temperature for 24 h. The solvent was removed in vacuo to give crude producs, which was purified by flash chromatography (silica gel, dichloromethane). Spectroscopic data for the major isomer are given below. IR (KBr): ν: 3429, 2920, 1608, 1512, 1250, 1036 cm-1. 1H NMR (250 MHz, CDCl3, J Hz) δ: 8.09 (d, 1H, J=7.5 Hz, CH arom); 7.91 (d, 1H, J=7.5 Hz, CH arom.); 7.56 (t, 1H, J=7.5 Hz, CH arom.); 7.42 (t, 1H, J=7.5 Hz, CH arom); 7.33–7.30 (m, 3H, CH arom.); 7.21–7.18 (m, 2H, CH arom.); 6.92–6.83 (m, 2H, H arom.); 6.74–6.67 (m, 1H, CH arom.); 6.45 (d, 1H, J= 7.5 Hz, CH arom.); 5.60 (s, 1H, H2); 5.06 (d, 1H, J= 18.5 Hz, Hb); 4.62 (d, 1H, J=18.5 Hz, Ha); 4.51 (s, 1H, H3); 3.26 (s, 1H, OH). 13 C NMR (62.9 MHz, CDCl3) δ: 148.1; 141.1; 139.7; 138.3; 134.1; 134.0; 133.7; 129.0; 130.0; 128.3; 128.0; 126.9; 125.3; 122.9; 117.9; 117.5; 110.6; 92.7; 64.3; 50.2. HRMS: (M+H)+, found 363.1347, C₂₁H₁₉N₂O₄ requires 363.1345.

Computing details top

Data collection: APEX2 (Bruker, 2011); cell refinement: SAINT (Bruker, 2011); data reduction: SAINT (Bruker, 2011); program(s) used to solve structure: SIR2002 (Burla et al., 2003); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012) and DIAMOND (Brandenburg & Berndt, 2001); software used to prepare material for publication: WinGX publication routines (Farrugia, 2012).

Figures top

	Fig. 1. The title molecule (Farrugia, 2012) with the atomic labelling scheme. The displacement parameters are drawn at the 50% probability level.
	Fig. 2. (Brandenburg & Berndt, 2001) Part of the crystal structure viewed down the b axis showing alternating layers and O—H···O hydrogene bond (in red)and O—H···π interactions.

4-(2-Nitrobenzyl)-3-phenyl-3,4-dihydro-2H-1,4-benzoxazin-2-ol top

Crystal data top

C₂₁H₁₈N₂O₄	F(000) = 1520
M_r = 362.37	D_x = 1.393 Mg m⁻³
Orthorhombic, Pna2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2n	Cell parameters from 4509 reflections
a = 12.7332 (14) Å	θ = 2.4–24.4°
b = 14.2777 (14) Å	µ = 0.10 mm⁻¹
c = 19.003 (2) Å	T = 150 K
V = 3454.8 (6) Å³	Stick, colourless
Z = 8	0.13 × 0.05 × 0.03 mm

Data collection top

Bruker APEXII CCD area-detector diffractometer	4907 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.052
ϕ and ω scans	θ_max = 25.1°, θ_min = 2.9°
Absorption correction: multi-scan (SADABS; Sheldrick, 2002)	h = −15→14
T_min = 0.860, T_max = 1.000	k = −17→16
19156 measured reflections	l = −20→22
3161 independent 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)] = 0.043	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.114	H-atom parameters constrained
S = 1.04	w = 1/[σ²(F_o²) + (0.0733P)² + 1.1329P] where P = (F_o² + 2F_c²)/3
3161 reflections	(Δ/σ)_max < 0.001
489 parameters	Δρ_max = 0.71 e Å⁻³
1 restraint	Δρ_min = −0.26 e Å⁻³

Crystal data top

C₂₁H₁₈N₂O₄	V = 3454.8 (6) Å³
M_r = 362.37	Z = 8
Orthorhombic, Pna2₁	Mo Kα radiation
a = 12.7332 (14) Å	µ = 0.10 mm⁻¹
b = 14.2777 (14) Å	T = 150 K
c = 19.003 (2) Å	0.13 × 0.05 × 0.03 mm

Data collection top

Bruker APEXII CCD area-detector diffractometer	3161 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 2002)	4907 reflections with I > 2σ(I)
T_min = 0.860, T_max = 1.000	R_int = 0.052
19156 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.043	1 restraint
wR(F²) = 0.114	H-atom parameters constrained
S = 1.04	Δρ_max = 0.71 e Å⁻³
3161 reflections	Δρ_min = −0.26 e Å⁻³
489 parameters

Special details top

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

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

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

	x	y	z	U_iso*/U_eq
O1A	0.35335 (19)	0.31206 (17)	0.27744 (14)	0.0169 (6)
O1B	0.08759 (19)	0.32183 (18)	0.40303 (14)	0.0188 (6)
O2B	−0.0900 (2)	0.35721 (17)	0.41491 (15)	0.0223 (6)
H2B	−0.0909	0.3919	0.3805	0.034*
O2A	0.1747 (2)	0.3367 (2)	0.26572 (16)	0.0290 (7)
H2A	0.1429	0.3446	0.3028	0.043*
O22B	−0.0711 (3)	0.2367 (2)	0.80910 (16)	0.0368 (8)
O21B	−0.0793 (3)	0.13604 (19)	0.72486 (16)	0.0353 (8)
O22A	0.1994 (3)	0.1316 (2)	−0.04698 (17)	0.0341 (7)
C20A	0.4687 (3)	0.4126 (2)	0.2155 (2)	0.0157 (8)
H20A	0.4941	0.4337	0.2585	0.019*
N1A	0.2735 (2)	0.2432 (2)	0.15006 (17)	0.0156 (7)
N1B	−0.0003 (2)	0.2559 (2)	0.52882 (17)	0.0157 (6)
N2B	−0.0921 (3)	0.2144 (2)	0.74825 (18)	0.0230 (8)
C16A	0.3515 (3)	0.3115 (2)	0.1502 (2)	0.0142 (7)
C8A	0.2519 (3)	0.2689 (3)	0.2753 (2)	0.0168 (8)
H8A	0.2393	0.2368	0.3201	0.02*
C10A	0.3123 (3)	0.1121 (2)	0.23395 (18)	0.0151 (8)
C4A	0.0388 (3)	0.4109 (3)	0.0605 (2)	0.0281 (10)
H4A	0.0101	0.4577	0.0886	0.034*
C5B	−0.2489 (3)	0.4199 (3)	0.6959 (2)	0.0275 (9)
H5B	−0.294	0.4629	0.7168	0.033*
N2A	0.1720 (3)	0.2069 (2)	−0.06923 (18)	0.0265 (8)
C13A	0.4302 (3)	−0.0451 (3)	0.2722 (2)	0.0223 (9)
H13A	0.4693	−0.0974	0.2849	0.027*
C14A	0.4782 (3)	0.0306 (3)	0.2398 (2)	0.0222 (9)
H14A	0.55	0.0292	0.2309	0.027*
C18A	0.4715 (3)	0.4166 (2)	0.0898 (2)	0.0173 (8)
H18A	0.4984	0.4405	0.048	0.021*
C19B	0.2465 (3)	0.4503 (3)	0.5305 (2)	0.0242 (9)
H19B	0.302	0.4927	0.5306	0.029*
C6A	0.0553 (3)	0.3375 (3)	−0.0502 (2)	0.0279 (10)
H6A	0.0382	0.3337	−0.0977	0.033*
C1A	0.2318 (3)	0.2083 (2)	0.0850 (2)	0.0159 (8)
H1A1	0.1954	0.1499	0.0939	0.019*
H1A2	0.2894	0.1953	0.0531	0.019*
C13B	0.1290 (3)	−0.0456 (3)	0.4143 (2)	0.0211 (9)
H13B	0.1623	−0.1022	0.4048	0.025*
C10B	0.0285 (3)	0.1225 (2)	0.44585 (19)	0.0143 (7)
C18B	0.2053 (3)	0.4181 (3)	0.5926 (2)	0.0231 (9)
H18B	0.2331	0.4392	0.6349	0.028*
C9A	0.2468 (3)	0.1974 (2)	0.21582 (19)	0.0148 (8)
H9A	0.1736	0.1766	0.2121	0.018*
C8B	−0.0167 (3)	0.2854 (2)	0.4040 (2)	0.0184 (8)
H8B	−0.0311	0.2556	0.3585	0.022*
C20B	0.2038 (3)	0.4185 (2)	0.4669 (2)	0.0190 (8)
H20B	0.2302	0.4405	0.4244	0.023*
C21A	0.3903 (3)	0.3462 (2)	0.21365 (19)	0.0138 (8)
C15A	0.4194 (3)	0.1085 (3)	0.2206 (2)	0.0197 (8)
H15A	0.4522	0.1588	0.1986	0.024*
O21A	0.1778 (3)	0.2291 (3)	−0.13132 (18)	0.0549 (11)
C12A	0.3238 (3)	−0.0421 (3)	0.2855 (2)	0.0253 (9)
H12A	0.2911	−0.0926	0.3073	0.03*
C12B	0.0268 (3)	−0.0320 (3)	0.39325 (19)	0.0186 (8)
H12B	−0.0085	−0.0787	0.3686	0.022*
C17A	0.3930 (3)	0.3493 (2)	0.0882 (2)	0.0161 (8)
H17A	0.3675	0.3288	0.045	0.019*
C16B	0.0804 (3)	0.3195 (2)	0.5305 (2)	0.0150 (8)
C6B	−0.2018 (3)	0.3512 (3)	0.7354 (2)	0.0246 (9)
H6B	−0.213	0.3481	0.7837	0.03*
C7B	−0.1375 (3)	0.2867 (3)	0.7026 (2)	0.0180 (8)
C3A	0.1106 (3)	0.3480 (3)	0.0891 (2)	0.0203 (8)
H3A	0.1288	0.3538	0.1363	0.024*
C1B	−0.0440 (3)	0.2183 (2)	0.5937 (2)	0.0184 (8)
H1B1	0.013	0.2008	0.6249	0.022*
H1B2	−0.0838	0.1621	0.583	0.022*
C17B	0.1231 (3)	0.3546 (3)	0.5934 (2)	0.0190 (8)
H17B	0.0956	0.3349	0.6363	0.023*
C19A	0.5096 (3)	0.4480 (2)	0.1537 (2)	0.0196 (8)
H19A	0.5626	0.4928	0.1551	0.023*
C2B	−0.1151 (3)	0.2880 (2)	0.6311 (2)	0.0149 (8)
C7A	0.1272 (3)	0.2745 (3)	−0.0214 (2)	0.0193 (8)
C5A	0.0100 (3)	0.4046 (3)	−0.0091 (2)	0.0309 (10)
H5A	−0.0396	0.4454	−0.0279	0.037*
C4B	−0.2285 (3)	0.4243 (3)	0.6249 (2)	0.0237 (9)
H4B	−0.2596	0.4709	0.5978	0.028*
C2A	0.1559 (3)	0.2770 (2)	0.0497 (2)	0.0157 (8)
C15B	0.1323 (3)	0.1074 (3)	0.4654 (2)	0.0201 (8)
H15B	0.1686	0.1539	0.4896	0.024*
C21B	0.1224 (3)	0.3544 (3)	0.4673 (2)	0.0166 (8)
C11A	0.2657 (3)	0.0354 (3)	0.2666 (2)	0.0199 (8)
H11A	0.194	0.0365	0.2759	0.024*
C3B	−0.1625 (3)	0.3602 (3)	0.5934 (2)	0.0199 (8)
H3B	−0.1491	0.3654	0.5454	0.024*
C14B	0.1824 (3)	0.0243 (3)	0.4494 (2)	0.0228 (9)
H14B	0.2521	0.0154	0.4624	0.027*
C9B	−0.0301 (3)	0.2126 (3)	0.46218 (19)	0.0163 (8)
H9B	−0.1051	0.1973	0.465	0.02*
C11B	−0.0240 (3)	0.0526 (2)	0.40908 (19)	0.0177 (8)
H11B	−0.0931	0.0619	0.3949	0.021*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1A	0.0165 (14)	0.0217 (13)	0.0126 (13)	−0.0024 (10)	−0.0029 (11)	−0.0010 (11)
O1B	0.0179 (14)	0.0223 (13)	0.0162 (14)	−0.0010 (11)	−0.0002 (11)	−0.0038 (10)
O2B	0.0200 (15)	0.0231 (14)	0.0240 (15)	0.0070 (11)	−0.0034 (12)	0.0018 (11)
O2A	0.0266 (16)	0.0328 (15)	0.0277 (17)	0.0095 (13)	0.0048 (13)	0.0000 (13)
O22B	0.065 (2)	0.0267 (16)	0.0185 (18)	0.0054 (15)	−0.0077 (15)	−0.0012 (13)
O21B	0.063 (2)	0.0168 (15)	0.0258 (17)	0.0039 (13)	0.0028 (16)	−0.0007 (12)
O22A	0.049 (2)	0.0251 (16)	0.0287 (17)	0.0089 (14)	−0.0047 (15)	−0.0047 (13)
C20A	0.0142 (18)	0.0158 (17)	0.0170 (19)	0.0008 (15)	−0.0041 (15)	−0.0056 (15)
N1A	0.0174 (16)	0.0162 (15)	0.0132 (16)	−0.0016 (13)	−0.0005 (13)	0.0023 (12)
N1B	0.0185 (16)	0.0180 (15)	0.0107 (16)	−0.0047 (13)	−0.0003 (13)	−0.0038 (13)
N2B	0.029 (2)	0.0204 (18)	0.0195 (19)	−0.0011 (14)	0.0045 (15)	0.0010 (14)
C16A	0.0096 (18)	0.0136 (17)	0.020 (2)	0.0007 (14)	−0.0004 (15)	−0.0009 (14)
C8A	0.0119 (17)	0.0217 (18)	0.017 (2)	0.0025 (14)	0.0003 (15)	0.0050 (15)
C10A	0.0170 (19)	0.0183 (18)	0.0100 (18)	0.0005 (15)	0.0015 (15)	−0.0036 (14)
C4A	0.024 (2)	0.028 (2)	0.032 (2)	0.0089 (19)	0.0022 (18)	−0.0013 (18)
C5B	0.021 (2)	0.029 (2)	0.033 (2)	0.0070 (18)	0.0082 (18)	−0.0042 (18)
N2A	0.036 (2)	0.0277 (19)	0.016 (2)	0.0025 (16)	−0.0012 (16)	0.0003 (14)
C13A	0.030 (2)	0.0200 (19)	0.017 (2)	0.0072 (16)	0.0006 (17)	−0.0013 (15)
C14A	0.0176 (19)	0.0186 (19)	0.030 (2)	0.0043 (15)	0.0035 (17)	−0.0020 (16)
C18A	0.0161 (19)	0.0146 (18)	0.021 (2)	0.0003 (16)	0.0007 (16)	0.0043 (15)
C19B	0.0126 (19)	0.0184 (19)	0.042 (3)	−0.0017 (15)	−0.0027 (18)	−0.0051 (18)
C6A	0.031 (2)	0.035 (2)	0.017 (2)	−0.0023 (19)	−0.0083 (19)	0.0076 (17)
C1A	0.0109 (18)	0.0176 (19)	0.019 (2)	−0.0025 (14)	−0.0031 (16)	−0.0023 (15)
C13B	0.033 (2)	0.0149 (18)	0.0155 (19)	0.0057 (16)	0.0098 (18)	−0.0005 (14)
C10B	0.0158 (18)	0.0165 (17)	0.0107 (18)	−0.0038 (14)	0.0017 (15)	0.0011 (14)
C18B	0.018 (2)	0.021 (2)	0.031 (2)	0.0032 (17)	−0.0048 (18)	−0.0104 (17)
C9A	0.0119 (18)	0.0184 (18)	0.0140 (19)	−0.0021 (14)	0.0011 (15)	0.0037 (14)
C8B	0.0165 (19)	0.0211 (19)	0.018 (2)	0.0013 (15)	−0.0035 (16)	−0.0037 (15)
C20B	0.0143 (19)	0.0160 (19)	0.027 (2)	0.0021 (15)	0.0031 (16)	0.0010 (16)
C21A	0.0116 (17)	0.0175 (19)	0.0122 (19)	0.0048 (14)	−0.0011 (15)	0.0021 (14)
C15A	0.019 (2)	0.0181 (19)	0.022 (2)	0.0004 (15)	0.0054 (17)	0.0004 (16)
O21A	0.085 (3)	0.058 (2)	0.022 (2)	0.031 (2)	0.0133 (19)	0.0036 (16)
C12A	0.030 (2)	0.0213 (19)	0.024 (2)	−0.0002 (17)	0.0033 (19)	0.0067 (17)
C12B	0.025 (2)	0.0182 (18)	0.0129 (19)	−0.0037 (15)	0.0028 (16)	−0.0066 (14)
C17A	0.0142 (19)	0.0178 (19)	0.0162 (19)	0.0020 (15)	−0.0026 (16)	0.0007 (15)
C16B	0.0121 (18)	0.0182 (18)	0.0148 (19)	0.0053 (15)	−0.0020 (15)	−0.0042 (14)
C6B	0.026 (2)	0.031 (2)	0.017 (2)	−0.0018 (18)	0.0058 (17)	0.0006 (16)
C7B	0.0161 (19)	0.017 (2)	0.021 (2)	−0.0041 (15)	0.0012 (16)	0.0028 (15)
C3A	0.019 (2)	0.023 (2)	0.020 (2)	0.0020 (16)	−0.0004 (17)	−0.0026 (16)
C1B	0.021 (2)	0.0147 (18)	0.020 (2)	−0.0007 (16)	−0.0014 (17)	−0.0009 (15)
C17B	0.018 (2)	0.021 (2)	0.018 (2)	0.0023 (16)	−0.0016 (16)	−0.0041 (15)
C19A	0.0130 (18)	0.0157 (18)	0.030 (2)	−0.0009 (15)	−0.0030 (17)	0.0003 (16)
C2B	0.0112 (18)	0.0133 (17)	0.020 (2)	−0.0040 (14)	0.0000 (15)	−0.0005 (14)
C7A	0.022 (2)	0.020 (2)	0.015 (2)	−0.0036 (15)	−0.0007 (16)	0.0013 (15)
C5A	0.024 (2)	0.035 (2)	0.034 (3)	0.013 (2)	−0.0023 (19)	0.0071 (19)
C4B	0.017 (2)	0.024 (2)	0.030 (2)	0.0067 (17)	−0.0015 (17)	0.0034 (17)
C2A	0.0142 (18)	0.0144 (18)	0.019 (2)	−0.0053 (15)	−0.0010 (15)	0.0039 (14)
C15B	0.018 (2)	0.020 (2)	0.022 (2)	0.0006 (16)	−0.0007 (16)	−0.0030 (16)
C21B	0.015 (2)	0.0167 (19)	0.018 (2)	0.0022 (15)	0.0002 (16)	−0.0049 (15)
C11A	0.015 (2)	0.027 (2)	0.017 (2)	−0.0021 (16)	0.0008 (15)	0.0062 (15)
C3B	0.018 (2)	0.023 (2)	0.018 (2)	0.0012 (16)	−0.0009 (16)	0.0009 (16)
C14B	0.018 (2)	0.027 (2)	0.022 (2)	0.0055 (16)	−0.0006 (17)	0.0008 (17)
C9B	0.0094 (18)	0.025 (2)	0.014 (2)	−0.0016 (15)	−0.0006 (15)	−0.0039 (15)
C11B	0.0180 (19)	0.0220 (19)	0.0130 (19)	−0.0021 (15)	0.0006 (16)	−0.0012 (15)

Geometric parameters (Å, º) top

O1A—C21A	1.389 (4)	C6A—C7A	1.395 (6)
O1A—C8A	1.432 (4)	C6A—H6A	0.93
O1B—C21B	1.379 (5)	C1A—C2A	1.532 (5)
O1B—C8B	1.426 (4)	C1A—H1A1	0.97
O2B—C8B	1.402 (4)	C1A—H1A2	0.97
O2B—H2B	0.82	C13B—C12B	1.375 (6)
O2A—C8A	1.391 (4)	C13B—C14B	1.380 (6)
O2A—H2A	0.82	C13B—H13B	0.93
O22B—N2B	1.229 (5)	C10B—C11B	1.390 (5)
O21B—N2B	1.215 (4)	C10B—C15B	1.390 (5)
O22A—N2A	1.207 (4)	C10B—C9B	1.519 (5)
C20A—C21A	1.376 (5)	C18B—C17B	1.385 (6)
C20A—C19A	1.380 (6)	C18B—H18B	0.93
C20A—H20A	0.93	C9A—H9A	0.98
N1A—C16A	1.393 (4)	C8B—C9B	1.527 (5)
N1A—C1A	1.434 (5)	C8B—H8B	0.98
N1A—C9A	1.451 (5)	C20B—C21B	1.382 (5)
N1B—C16B	1.372 (5)	C20B—H20B	0.93
N1B—C1B	1.455 (5)	C15A—H15A	0.93
N1B—C9B	1.459 (5)	C12A—C11A	1.379 (5)
N2B—C7B	1.467 (5)	C12A—H12A	0.93
C16A—C21A	1.393 (5)	C12B—C11B	1.403 (5)
C16A—C17A	1.401 (5)	C12B—H12B	0.93
C8A—C9A	1.524 (5)	C17A—H17A	0.93
C8A—H8A	0.98	C16B—C17B	1.406 (5)
C10A—C15A	1.389 (5)	C16B—C21B	1.407 (5)
C10A—C11A	1.392 (5)	C6B—C7B	1.381 (6)
C10A—C9A	1.516 (5)	C6B—H6B	0.93
C4A—C5A	1.375 (6)	C7B—C2B	1.389 (6)
C4A—C3A	1.393 (6)	C3A—C2A	1.386 (5)
C4A—H4A	0.93	C3A—H3A	0.93
C5B—C6B	1.375 (6)	C1B—C2B	1.522 (5)
C5B—C4B	1.376 (6)	C1B—H1B1	0.97
C5B—H5B	0.93	C1B—H1B2	0.97
N2A—O21A	1.224 (5)	C17B—H17B	0.93
N2A—C7A	1.443 (5)	C19A—H19A	0.93
C13A—C12A	1.378 (6)	C2B—C3B	1.393 (5)
C13A—C14A	1.386 (5)	C7A—C2A	1.401 (6)
C13A—H13A	0.93	C5A—H5A	0.93
C14A—C15A	1.390 (5)	C4B—C3B	1.378 (6)
C14A—H14A	0.93	C4B—H4B	0.93
C18A—C19A	1.384 (6)	C15B—C14B	1.381 (5)
C18A—C17A	1.386 (5)	C15B—H15B	0.93
C18A—H18A	0.93	C11A—H11A	0.93
C19B—C18B	1.370 (6)	C3B—H3B	0.93
C19B—C20B	1.401 (6)	C14B—H14B	0.93
C19B—H19B	0.93	C9B—H9B	0.98
C6A—C5A	1.363 (6)	C11B—H11B	0.93

C21A—O1A—C8A	115.6 (3)	C21B—C20B—H20B	119.9
C21B—O1B—C8B	114.3 (3)	C19B—C20B—H20B	119.9
C8B—O2B—H2B	109.5	C20A—C21A—O1A	117.8 (3)
C8A—O2A—H2A	109.5	C20A—C21A—C16A	121.6 (3)
C21A—C20A—C19A	120.3 (3)	O1A—C21A—C16A	120.6 (3)
C21A—C20A—H20A	119.8	C10A—C15A—C14A	120.7 (4)
C19A—C20A—H20A	119.8	C10A—C15A—H15A	119.6
C16A—N1A—C1A	120.6 (3)	C14A—C15A—H15A	119.6
C16A—N1A—C9A	118.7 (3)	C13A—C12A—C11A	120.3 (4)
C1A—N1A—C9A	119.9 (3)	C13A—C12A—H12A	119.9
C16B—N1B—C1B	120.7 (3)	C11A—C12A—H12A	119.9
C16B—N1B—C9B	119.7 (3)	C13B—C12B—C11B	119.7 (3)
C1B—N1B—C9B	118.6 (3)	C13B—C12B—H12B	120.2
O21B—N2B—O22B	123.6 (4)	C11B—C12B—H12B	120.2
O21B—N2B—C7B	119.0 (3)	C18A—C17A—C16A	121.4 (4)
O22B—N2B—C7B	117.4 (3)	C18A—C17A—H17A	119.3
N1A—C16A—C21A	120.3 (3)	C16A—C17A—H17A	119.3
N1A—C16A—C17A	122.5 (3)	N1B—C16B—C17B	123.1 (3)
C21A—C16A—C17A	117.2 (3)	N1B—C16B—C21B	120.0 (3)
O2A—C8A—O1A	110.0 (3)	C17B—C16B—C21B	116.9 (3)
O2A—C8A—C9A	109.8 (3)	C5B—C6B—C7B	119.2 (4)
O1A—C8A—C9A	110.4 (3)	C5B—C6B—H6B	120.4
O2A—C8A—H8A	108.9	C7B—C6B—H6B	120.4
O1A—C8A—H8A	108.9	C6B—C7B—C2B	123.7 (4)
C9A—C8A—H8A	108.9	C6B—C7B—N2B	115.8 (3)
C15A—C10A—C11A	118.1 (3)	C2B—C7B—N2B	120.5 (3)
C15A—C10A—C9A	122.0 (3)	C2A—C3A—C4A	122.2 (4)
C11A—C10A—C9A	119.9 (3)	C2A—C3A—H3A	118.9
C5A—C4A—C3A	120.6 (4)	C4A—C3A—H3A	118.9
C5A—C4A—H4A	119.7	N1B—C1B—C2B	112.4 (3)
C3A—C4A—H4A	119.7	N1B—C1B—H1B1	109.1
C6B—C5B—C4B	119.1 (4)	C2B—C1B—H1B1	109.1
C6B—C5B—H5B	120.5	N1B—C1B—H1B2	109.1
C4B—C5B—H5B	120.5	C2B—C1B—H1B2	109.1
O22A—N2A—O21A	123.4 (4)	H1B1—C1B—H1B2	107.9
O22A—N2A—C7A	119.3 (3)	C18B—C17B—C16B	121.1 (4)
O21A—N2A—C7A	117.2 (3)	C18B—C17B—H17B	119.5
C12A—C13A—C14A	119.4 (4)	C16B—C17B—H17B	119.5
C12A—C13A—H13A	120.3	C20A—C19A—C18A	119.7 (3)
C14A—C13A—H13A	120.3	C20A—C19A—H19A	120.2
C13A—C14A—C15A	120.2 (4)	C18A—C19A—H19A	120.2
C13A—C14A—H14A	119.9	C7B—C2B—C3B	115.1 (3)
C15A—C14A—H14A	119.9	C7B—C2B—C1B	124.7 (3)
C19A—C18A—C17A	119.8 (4)	C3B—C2B—C1B	120.1 (4)
C19A—C18A—H18A	120.1	C6A—C7A—C2A	122.2 (4)
C17A—C18A—H18A	120.1	C6A—C7A—N2A	116.4 (4)
C18B—C19B—C20B	119.0 (4)	C2A—C7A—N2A	121.4 (3)
C18B—C19B—H19B	120.5	C6A—C5A—C4A	118.9 (4)
C20B—C19B—H19B	120.5	C6A—C5A—H5A	120.6
C5A—C6A—C7A	120.5 (4)	C4A—C5A—H5A	120.6
C5A—C6A—H6A	119.8	C5B—C4B—C3B	120.7 (4)
C7A—C6A—H6A	119.8	C5B—C4B—H4B	119.6
N1A—C1A—C2A	112.9 (3)	C3B—C4B—H4B	119.6
N1A—C1A—H1A1	109	C3A—C2A—C7A	115.6 (4)
C2A—C1A—H1A1	109	C3A—C2A—C1A	119.6 (3)
N1A—C1A—H1A2	109	C7A—C2A—C1A	124.8 (3)
C2A—C1A—H1A2	109	C14B—C15B—C10B	120.9 (4)
H1A1—C1A—H1A2	107.8	C14B—C15B—H15B	119.5
C12B—C13B—C14B	120.3 (3)	C10B—C15B—H15B	119.5
C12B—C13B—H13B	119.8	O1B—C21B—C20B	117.4 (3)
C14B—C13B—H13B	119.8	O1B—C21B—C16B	121.0 (3)
C11B—C10B—C15B	118.7 (3)	C20B—C21B—C16B	121.6 (4)
C11B—C10B—C9B	118.3 (3)	C12A—C11A—C10A	121.3 (4)
C15B—C10B—C9B	123.0 (3)	C12A—C11A—H11A	119.4
C19B—C18B—C17B	121.3 (4)	C10A—C11A—H11A	119.4
C19B—C18B—H18B	119.4	C4B—C3B—C2B	122.1 (4)
C17B—C18B—H18B	119.4	C4B—C3B—H3B	118.9
N1A—C9A—C10A	115.4 (3)	C2B—C3B—H3B	118.9
N1A—C9A—C8A	109.0 (3)	C13B—C14B—C15B	120.0 (4)
C10A—C9A—C8A	110.3 (3)	C13B—C14B—H14B	120
N1A—C9A—H9A	107.3	C15B—C14B—H14B	120
C10A—C9A—H9A	107.3	N1B—C9B—C10B	114.1 (3)
C8A—C9A—H9A	107.3	N1B—C9B—C8B	108.1 (3)
O2B—C8B—O1B	110.8 (3)	C10B—C9B—C8B	111.9 (3)
O2B—C8B—C9B	108.4 (3)	N1B—C9B—H9B	107.5
O1B—C8B—C9B	111.2 (3)	C10B—C9B—H9B	107.5
O2B—C8B—H8B	108.8	C8B—C9B—H9B	107.5
O1B—C8B—H8B	108.8	C10B—C11B—C12B	120.3 (3)
C9B—C8B—H8B	108.8	C10B—C11B—H11B	119.8
C21B—C20B—C19B	120.1 (4)	C12B—C11B—H11B	119.8

C1A—N1A—C16A—C21A	178.9 (3)	C21A—C20A—C19A—C18A	0.1 (5)
C9A—N1A—C16A—C21A	−10.7 (5)	C17A—C18A—C19A—C20A	−0.5 (5)
C1A—N1A—C16A—C17A	−0.1 (5)	C6B—C7B—C2B—C3B	0.0 (5)
C9A—N1A—C16A—C17A	170.3 (3)	N2B—C7B—C2B—C3B	−179.8 (3)
C21A—O1A—C8A—O2A	−71.7 (4)	C6B—C7B—C2B—C1B	179.6 (4)
C21A—O1A—C8A—C9A	49.7 (4)	N2B—C7B—C2B—C1B	−0.2 (6)
C12A—C13A—C14A—C15A	−0.3 (6)	N1B—C1B—C2B—C7B	−156.3 (3)
C16A—N1A—C1A—C2A	−75.7 (4)	N1B—C1B—C2B—C3B	23.2 (5)
C9A—N1A—C1A—C2A	114.0 (3)	C5A—C6A—C7A—C2A	0.0 (6)
C20B—C19B—C18B—C17B	0.3 (6)	C5A—C6A—C7A—N2A	−179.2 (4)
C16A—N1A—C9A—C10A	−87.3 (4)	O22A—N2A—C7A—C6A	−151.1 (4)
C1A—N1A—C9A—C10A	83.1 (4)	O21A—N2A—C7A—C6A	27.3 (6)
C16A—N1A—C9A—C8A	37.4 (4)	O22A—N2A—C7A—C2A	29.7 (6)
C1A—N1A—C9A—C8A	−152.2 (3)	O21A—N2A—C7A—C2A	−151.9 (4)
C15A—C10A—C9A—N1A	38.8 (5)	C7A—C6A—C5A—C4A	2.0 (7)
C11A—C10A—C9A—N1A	−142.9 (3)	C3A—C4A—C5A—C6A	−2.1 (7)
C15A—C10A—C9A—C8A	−85.3 (4)	C6B—C5B—C4B—C3B	0.6 (7)
C11A—C10A—C9A—C8A	93.0 (4)	C4A—C3A—C2A—C7A	1.9 (6)
O2A—C8A—C9A—N1A	65.3 (4)	C4A—C3A—C2A—C1A	−178.2 (4)
O1A—C8A—C9A—N1A	−56.1 (4)	C6A—C7A—C2A—C3A	−1.9 (6)
O2A—C8A—C9A—C10A	−167.0 (3)	N2A—C7A—C2A—C3A	177.3 (3)
O1A—C8A—C9A—C10A	71.5 (4)	C6A—C7A—C2A—C1A	178.1 (4)
C21B—O1B—C8B—O2B	68.7 (4)	N2A—C7A—C2A—C1A	−2.7 (6)
C21B—O1B—C8B—C9B	−51.9 (4)	N1A—C1A—C2A—C3A	−19.0 (5)
C18B—C19B—C20B—C21B	−1.0 (5)	N1A—C1A—C2A—C7A	161.0 (3)
C19A—C20A—C21A—O1A	179.0 (3)	C11B—C10B—C15B—C14B	−0.7 (6)
C19A—C20A—C21A—C16A	1.3 (5)	C9B—C10B—C15B—C14B	180.0 (4)
C8A—O1A—C21A—C20A	159.9 (3)	C8B—O1B—C21B—C20B	−158.0 (3)
C8A—O1A—C21A—C16A	−22.3 (4)	C8B—O1B—C21B—C16B	25.5 (5)
N1A—C16A—C21A—C20A	178.9 (3)	C19B—C20B—C21B—O1B	−176.5 (3)
C17A—C16A—C21A—C20A	−2.1 (5)	C19B—C20B—C21B—C16B	0.0 (5)
N1A—C16A—C21A—O1A	1.2 (5)	N1B—C16B—C21B—O1B	−3.5 (5)
C17A—C16A—C21A—O1A	−179.7 (3)	C17B—C16B—C21B—O1B	178.0 (3)
C11A—C10A—C15A—C14A	−0.4 (6)	N1B—C16B—C21B—C20B	−179.9 (3)
C9A—C10A—C15A—C14A	178.0 (3)	C17B—C16B—C21B—C20B	1.6 (5)
C13A—C14A—C15A—C10A	0.4 (6)	C13A—C12A—C11A—C10A	0.0 (6)
C14A—C13A—C12A—C11A	0.1 (6)	C15A—C10A—C11A—C12A	0.2 (6)
C14B—C13B—C12B—C11B	−1.4 (6)	C9A—C10A—C11A—C12A	−178.2 (4)
C19A—C18A—C17A—C16A	−0.4 (5)	C5B—C4B—C3B—C2B	1.0 (6)
N1A—C16A—C17A—C18A	−179.3 (3)	C7B—C2B—C3B—C4B	−1.3 (5)
C21A—C16A—C17A—C18A	1.7 (5)	C1B—C2B—C3B—C4B	179.1 (4)
C1B—N1B—C16B—C17B	−2.3 (5)	C12B—C13B—C14B—C15B	1.8 (6)
C9B—N1B—C16B—C17B	−171.1 (3)	C10B—C15B—C14B—C13B	−0.8 (6)
C1B—N1B—C16B—C21B	179.3 (3)	C16B—N1B—C9B—C10B	89.6 (4)
C9B—N1B—C16B—C21B	10.4 (5)	C1B—N1B—C9B—C10B	−79.4 (4)
C4B—C5B—C6B—C7B	−1.8 (6)	C16B—N1B—C9B—C8B	−35.5 (4)
C5B—C6B—C7B—C2B	1.5 (6)	C1B—N1B—C9B—C8B	155.4 (3)
C5B—C6B—C7B—N2B	−178.7 (4)	C11B—C10B—C9B—N1B	146.7 (3)
O21B—N2B—C7B—C6B	145.4 (4)	C15B—C10B—C9B—N1B	−33.9 (5)
O22B—N2B—C7B—C6B	−33.2 (5)	C11B—C10B—C9B—C8B	−90.2 (4)
O21B—N2B—C7B—C2B	−34.8 (5)	C15B—C10B—C9B—C8B	89.2 (4)
O22B—N2B—C7B—C2B	146.6 (4)	O2B—C8B—C9B—N1B	−66.3 (4)
C5A—C4A—C3A—C2A	0.0 (7)	O1B—C8B—C9B—N1B	55.8 (4)
C16B—N1B—C1B—C2B	75.9 (4)	O2B—C8B—C9B—C10B	167.3 (3)
C9B—N1B—C1B—C2B	−115.1 (3)	O1B—C8B—C9B—C10B	−70.7 (4)
C19B—C18B—C17B—C16B	1.4 (6)	C15B—C10B—C11B—C12B	1.0 (5)
N1B—C16B—C17B—C18B	179.3 (3)	C9B—C10B—C11B—C12B	−179.5 (3)
C21B—C16B—C17B—C18B	−2.3 (5)	C13B—C12B—C11B—C10B	0.0 (5)

Hydrogen-bond geometry (Å, º) top

Cg1 and Cg2 are the controids of the C10A–C15A and C10B–C15B rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
O2A—H2A···O1B	0.82	2.06	2.843 (4)	161
C6B—H6B···O21Aⁱ	0.93	2.40	3.175 (5)	141
C8B—H8B···O1Aⁱⁱ	0.98	2.34	3.234 (4)	151
C14A—H14A···O2Aⁱⁱⁱ	0.93	2.57	3.177 (5)	123
C19A—H19A···O21B^iv	0.93	2.45	3.134 (4)	131
C19B—H19B···O22A^v	0.93	2.47	3.057 (5)	121
O2B—H2B···Cg1ⁱⁱ	0.82	2.69	3.484 (3)	164
C18A—H18A···Cg2^iv	0.93	2.83	3.564 (4)	137
C18B—H18B···Cg1^v	0.93	2.94	3.601 (4)	130

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

Hydrogen-bond geometry (Å, º) top

Cg1 and Cg2 are the controids of the C10A–C15A and C10B–C15B rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
O2A—H2A···O1B	0.82	2.06	2.843 (4)	161
C6B—H6B···O21Aⁱ	0.93	2.40	3.175 (5)	141
C8B—H8B···O1Aⁱⁱ	0.98	2.34	3.234 (4)	151
C14A—H14A···O2Aⁱⁱⁱ	0.93	2.57	3.177 (5)	123
C19A—H19A···O21B^iv	0.93	2.45	3.134 (4)	131
C19B—H19B···O22A^v	0.93	2.47	3.057 (5)	121
O2B—H2B···Cg1ⁱⁱ	0.82	2.69	3.484 (3)	164
C18A—H18A···Cg2^iv	0.93	2.83	3.564 (4)	137
C18B—H18B···Cg1^v	0.93	2.94	3.601 (4)	130

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

Acknowledgements

We are grateful to all personnel of the Laboratoire de Synthèse des Molécules d'Intérêts Biologiques and UR–CHEMS, Université Constantine 1, Algeria, for their assistance. Thanks are due to the MESRS (Ministère de l'Enseignement Supérieur et de la Recherche Scientifique, Algeria) for financial support.

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Volume 70| Part 8| August 2014| Pages o863-o864

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