1,3-Bis(prop-2-yn-1-yl)-1H-anthra[1,2-d]imidazole-2,6,11(3H)-trione

Afrakssou, Z.; Haoudi, A.; Capet, F.; Mazzah, A.; Rolando, C.; El Ammari, L.

doi:10.1107/S1600536813013688

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 69| Part 6| June 2013| Page o944

doi:10.1107/S1600536813013688

Open

access

1,3-Bis(prop-2-yn-1-yl)-1H-anthra[1,2-d]imidazole-2,6,11(3H)-trione

Zahra Afrakssou,^a ^* Amal Haoudi,^a Frédéric Capet,^b Ahmed Mazzah,^c Christian Rolando ^c and Lahcen El Ammari ^d

^aLaboratoire de Chimie Organique Appliquée, Université Sidi Mohamed, Ben Abdallah, Faculté des Sciences et Techniques, Route d'Immouzzer, BP 2202 Fès, Morocco, ^bUnité de Catalyse et de Chimie du Solide (UCCS), UMR 8181 Ecole Nationale Supérieure de Chimie de Lille, France, ^cUSR 3290 Miniaturisation pour l'Analyse, la Synthèse et la Protéomique, 59655 Villeneuve d'Ascq Cedex, Université Lille 1, France, and ^dLaboratoire de Chimie du Solide Appliquée, Faculté des Sciences, Université Mohammed V-Agdal, Avenue Ibn Battouta, BP 1014, Rabat, Morocco
^*Correspondence e-mail: afrassou@yahoo.fr

(Received 7 May 2013; accepted 17 May 2013; online 22 May 2013)

In the title compound, C₂₁H₁₂N₂O₃, the fused-ring system is roughly planar, the largest deviation from the mean plane being 0.084 (2) Å. The two prop-2-yn-1-yl groups are almost perpendicular to the fused ring plane, making C—C—N—C torsion angles of −103.4 (2) and −105.3 (2)°, and point in opposite directions with respect to the plane. In the crystal, molecules are linked by weak C—H⋯O hydrogen bonds, forming a three-dimensional network.

Related literature

For background to the pharmacological activity and potential applications of anthraquinones, see: Alves et al. (2004 ); Ellis et al. (2003 ); Boseggia et al. (2004 ); Mariappan & Basa (2011 ); Kadarkaraisamy et al. (2008 ). For similar compounds, see: Afrakssou et al. (2010 , 2011 ); Guimarães et al. (2009 ).

Experimental

Crystal data

C₂₁H₁₂N₂O₃
M_r = 340.33
Monoclinic, P 2₁ /c
a = 16.6972 (5) Å
b = 4.5602 (1) Å
c = 21.2500 (5) Å
β = 96.352 (2)°
V = 1608.10 (7) Å³
Z = 4
Mo Kα radiation
μ = 0.10 mm⁻¹
T = 296 K
0.46 × 0.14 × 0.05 mm

Data collection

Bruker APEXII CCD diffractometer
20426 measured reflections
3177 independent reflections
2301 reflections with I > 2σ(I)
R_int = 0.033

Refinement

R[F² > 2σ(F²)] = 0.044
wR(F²) = 0.129
S = 1.02
3177 reflections
235 parameters
H-atom parameters constrained
Δρ_max = 0.33 e Å⁻³
Δρ_min = −0.25 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C18—H18⋯O2ⁱ	0.93	2.31	3.165 (3)	152
C21—H21⋯O1ⁱⁱ	0.93	2.38	3.275 (3)	161
C2—H2⋯O3ⁱⁱⁱ	0.93	2.62	3.333 (3)	134
Symmetry codes: (i) $[-x, y+{\script{3\over 2}}, -z+{\script{1\over 2}}]$ ; (ii) $[-x+1, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (iii) $[x, -y+{\script{3\over 2}}, z+{\script{1\over 2}}]$ .

Data collection: APEX2 (Bruker, 2009 ); cell refinement: SAINT-Plus (Bruker, 2009); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ); software used to prepare material for publication: PLATON (Spek, 2009 ) and publCIF (Westrip, 2010 ).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536813013688/im2432sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536813013688/im2432Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536813013688/im2432Isup3.cml

checkCIF report

Comment top

Anthraquinone-containing extracts from different plant sources such as senna, cascara, aloe, frangula, and rhubarb have been found to have a wide variety of pharmacological activities such as antiinflammatory, wound healing, analgesic, antipyretic, antimicrobial, and antitumor activities (Alves et al., 2004). Anthraquinone containing compounds are also important due to their potential applications as DNA intercalators (Ellis et al., 2003; Boseggia et al., 2004), as selective luminescent sensors of oxo-acids and metal ions when integrated into polyether chains (Mariappan & Basa, 2011) and as molecular switches (Kadarkaraisamy et al., 2008).

So we are interested in the synthesis of new derivatives of anthra [1,2-d]imidazole-2,6, 11–trione and their biological activities (Afrakssou et al., 2010; Afrakssou et al., (2011); Guimarães et al., 2009). The reactivity of propargyl bromide towards 1H-anthra [2, 1 - d] imidazole-2, 6, 11(3H)-trione under phase-transfer catalysis conditions using tetra n-butyl ammonium bromide (TBAB) as catalyst and potassium carbonate as base, leads to the formation of title compound in good yields (Scheme 1).

The four fused rings forming the molecule of the title compound are approximately planar, the largest deviation from the mean plane being 0.084 (2) Å at C10 (Fig. 1). The two prop-2-yn-1-yl (C16 to C18 and C19 to C21) groups are situated on opposite sides of the imidazole ring and are almost perpendicular to the fused rings plane, making C17–C16–N1–C15 and C20–C19–N2–C15 torsion angles of -103.4 (2) ° and -105.3 (2) °, respectively.

In the crystal, each molecule is linked to three adjacent molecules by intermolecular weak C18–H18···O2, C21–H21···O1 and C2–H2···O3 hydrogen bonds, forming a three-dimensional network (Fig. 2 and Table 2).

Related literature top

For background to the pharmacological activity and potential applications of anthraquinones, see: Alves et al. (2004); Ellis et al. (2003); Boseggia et al. (2004); Mariappan & Basa (2011); Kadarkaraisamy et al. (2008). For similar compounds, see: Afrakssou et al. (2010, 2011); Guimarães et al. (2009).

Experimental top

To a solution of 1H-anthra [2, 1 - d] imidazole-2, 6, 11(3H)-trione (0.05 g, 0.18 mmol), potassium carbonate (0.08 g, 0.56 mmol) and tetra n-butylammonium bromide (0.06 g, 0.018 mmol) in DMF (15 ml)) was added propargyl bromide (0.06 ml, 0.8 mmol). Stirring was continued at room temperature for 24 h. The mixture was filtered and the solvent removed. The residue was extracted with water. The organic compound was chromatographed on a column of silica gel with ethyl acetate-hexane (1/1) as eluent. Orange crystals were isolated when the solvent was allowed to evaporate (Yield: 65%).

Computing details top

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT-Plus (Bruker, 2009); data reduction: SAINT-Plus (Bruker, 2009); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012); software used to prepare material for publication: PLATON (Spek, 2009) and publCIF (Westrip, 2010).

Figures top

	Fig. 1. : Molecular structure of the title compound with the atom-labelling scheme. Displacement ellipsoids are drawn at the 50% probability level. H atoms are represented as small circles.
	Fig. 2. : Intermolecular interactions in the crystal structure of title compound. Hydrogen bonds are shown as dashed lines.

1,3-Bis(prop-2-yn-1-yl)-1H-anthra[1,2-d]imidazole-2,6,11(3H)-trione top

Crystal data top

C₂₁H₁₂N₂O₃	F(000) = 704
M_r = 340.33	D_x = 1.406 Mg m⁻³
Monoclinic, P2₁/c	Melting point: 463 K
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 16.6972 (5) Å	Cell parameters from 3177 reflections
b = 4.5602 (1) Å	θ = 2.5–26.0°
c = 21.2500 (5) Å	µ = 0.10 mm⁻¹
β = 96.352 (2)°	T = 296 K
V = 1608.10 (7) Å³	Irregular shape, yellow
Z = 4	0.46 × 0.14 × 0.05 mm

Data collection top

Bruker APEXII CCD diffractometer	2301 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.033
Graphite monochromator	θ_max = 26.0°, θ_min = 2.4°
ϕ and ω scans	h = −20→19
20426 measured reflections	k = −5→5
3177 independent reflections	l = −26→25

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)] = 0.044	Hydrogen site location: difference Fourier map
wR(F²) = 0.129	H-atom parameters constrained
S = 1.02	w = 1/[σ²(F_o²) + (0.0555P)² + 0.5235P] where P = (F_o² + 2F_c²)/3
3177 reflections	(Δ/σ)_max < 0.001
235 parameters	Δρ_max = 0.33 e Å⁻³
0 restraints	Δρ_min = −0.25 e Å⁻³

Crystal data top

C₂₁H₁₂N₂O₃	V = 1608.10 (7) Å³
M_r = 340.33	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 16.6972 (5) Å	µ = 0.10 mm⁻¹
b = 4.5602 (1) Å	T = 296 K
c = 21.2500 (5) Å	0.46 × 0.14 × 0.05 mm
β = 96.352 (2)°

Data collection top

Bruker APEXII CCD diffractometer	2301 reflections with I > 2σ(I)
20426 measured reflections	R_int = 0.033
3177 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.044	0 restraints
wR(F²) = 0.129	H-atom parameters constrained
S = 1.02	Δρ_max = 0.33 e Å⁻³
3177 reflections	Δρ_min = −0.25 e Å⁻³
235 parameters

Special details top

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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
C1	0.27182 (12)	0.6098 (4)	0.40077 (9)	0.0604 (5)
C2	0.28450 (15)	0.4803 (6)	0.46051 (10)	0.0812 (7)
H2	0.2480	0.3427	0.4725	0.097*
C3	0.35059 (19)	0.5550 (7)	0.50163 (11)	0.0980 (9)
H3	0.3581	0.4711	0.5417	0.118*
C4	0.40550 (18)	0.7526 (7)	0.48372 (12)	0.1005 (9)
H4	0.4507	0.7995	0.5115	0.121*
C5	0.39427 (14)	0.8828 (6)	0.42474 (10)	0.0811 (7)
H5	0.4320	1.0164	0.4130	0.097*
C6	0.32708 (12)	0.8154 (4)	0.38289 (8)	0.0581 (5)
C7	0.31375 (10)	0.9681 (4)	0.32094 (8)	0.0521 (5)
C8	0.24435 (9)	0.8852 (4)	0.27529 (8)	0.0447 (4)
C9	0.18813 (10)	0.6776 (4)	0.29414 (8)	0.0505 (4)
C10	0.20212 (12)	0.5247 (4)	0.35604 (9)	0.0595 (5)
C11	0.22732 (9)	1.0111 (4)	0.21489 (8)	0.0444 (4)
C12	0.15499 (10)	0.9328 (4)	0.17752 (8)	0.0500 (4)
C13	0.09989 (11)	0.7381 (4)	0.19747 (10)	0.0596 (5)
H13	0.0521	0.6955	0.1723	0.072*
C14	0.11783 (11)	0.6094 (4)	0.25560 (10)	0.0603 (5)
H14	0.0822	0.4735	0.2696	0.072*
C15	0.21803 (11)	1.2631 (4)	0.12116 (9)	0.0551 (5)
C16	0.09096 (12)	1.0549 (5)	0.06690 (9)	0.0677 (6)
H16A	0.0776	0.8490	0.0610	0.081*
H16B	0.1133	1.1226	0.0293	0.081*
C17	0.01719 (12)	1.2201 (5)	0.07407 (9)	0.0592 (5)
C18	−0.04129 (13)	1.3540 (5)	0.07967 (11)	0.0738 (6)
H18	−0.0878	1.4604	0.0841	0.089*
C19	0.34510 (10)	1.3565 (4)	0.18615 (9)	0.0546 (5)
H19A	0.3465	1.5073	0.1541	0.066*
H19B	0.3530	1.4511	0.2272	0.066*
C20	0.41099 (11)	1.1519 (4)	0.18097 (9)	0.0565 (5)
C21	0.46571 (13)	0.9943 (6)	0.17751 (11)	0.0821 (7)
H21	0.5092	0.8691	0.1748	0.099*
N1	0.15159 (9)	1.0865 (4)	0.12144 (7)	0.0558 (4)
N2	0.26525 (8)	1.2155 (3)	0.17856 (7)	0.0482 (4)
O1	0.35778 (9)	1.1731 (4)	0.31003 (6)	0.0812 (5)
O2	0.15706 (10)	0.3264 (3)	0.36931 (8)	0.0825 (5)
O3	0.23256 (9)	1.4307 (4)	0.07918 (6)	0.0718 (4)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0692 (12)	0.0584 (12)	0.0556 (11)	0.0081 (10)	0.0164 (9)	−0.0032 (9)
C2	0.1003 (18)	0.0830 (16)	0.0623 (13)	0.0040 (14)	0.0186 (13)	0.0081 (12)
C3	0.126 (2)	0.107 (2)	0.0583 (14)	0.0071 (19)	−0.0008 (15)	0.0138 (14)
C4	0.108 (2)	0.119 (2)	0.0669 (15)	−0.0052 (19)	−0.0214 (14)	0.0100 (16)
C5	0.0779 (15)	0.0963 (18)	0.0649 (13)	−0.0095 (13)	−0.0110 (11)	0.0053 (13)
C6	0.0610 (11)	0.0617 (12)	0.0516 (10)	0.0051 (10)	0.0058 (8)	−0.0054 (9)
C7	0.0453 (10)	0.0593 (11)	0.0525 (10)	−0.0035 (9)	0.0084 (8)	−0.0054 (9)
C8	0.0409 (9)	0.0431 (9)	0.0511 (9)	0.0031 (7)	0.0096 (7)	−0.0088 (8)
C9	0.0474 (10)	0.0460 (10)	0.0600 (10)	0.0002 (8)	0.0138 (8)	−0.0108 (9)
C10	0.0631 (12)	0.0512 (11)	0.0681 (12)	0.0017 (9)	0.0243 (10)	−0.0045 (10)
C11	0.0377 (8)	0.0418 (9)	0.0541 (9)	0.0030 (7)	0.0073 (7)	−0.0110 (8)
C12	0.0442 (9)	0.0505 (10)	0.0548 (10)	0.0048 (8)	0.0028 (7)	−0.0144 (9)
C13	0.0439 (10)	0.0633 (12)	0.0702 (12)	−0.0056 (9)	0.0003 (8)	−0.0207 (10)
C14	0.0505 (10)	0.0568 (11)	0.0754 (13)	−0.0096 (9)	0.0145 (9)	−0.0127 (10)
C15	0.0545 (11)	0.0581 (11)	0.0528 (10)	0.0102 (9)	0.0059 (8)	−0.0075 (10)
C16	0.0679 (13)	0.0758 (14)	0.0558 (11)	0.0085 (11)	−0.0094 (9)	−0.0183 (10)
C17	0.0515 (11)	0.0669 (13)	0.0565 (10)	−0.0073 (10)	−0.0066 (8)	−0.0058 (10)
C18	0.0527 (12)	0.0854 (16)	0.0807 (14)	−0.0005 (12)	−0.0038 (10)	−0.0060 (13)
C19	0.0516 (10)	0.0524 (11)	0.0604 (10)	−0.0036 (8)	0.0082 (8)	0.0000 (9)
C20	0.0461 (10)	0.0659 (12)	0.0573 (10)	−0.0024 (9)	0.0049 (8)	−0.0042 (10)
C21	0.0526 (12)	0.1004 (18)	0.0918 (16)	0.0151 (13)	0.0003 (11)	−0.0172 (14)
N1	0.0493 (9)	0.0611 (10)	0.0550 (9)	0.0049 (7)	−0.0038 (7)	−0.0128 (8)
N2	0.0423 (8)	0.0501 (8)	0.0519 (8)	0.0013 (6)	0.0036 (6)	−0.0032 (7)
O1	0.0712 (9)	0.1062 (13)	0.0632 (8)	−0.0379 (9)	−0.0060 (7)	0.0079 (8)
O2	0.0878 (11)	0.0711 (10)	0.0930 (11)	−0.0163 (9)	0.0289 (9)	0.0080 (9)
O3	0.0808 (10)	0.0764 (10)	0.0579 (8)	0.0050 (8)	0.0058 (7)	0.0079 (8)

Geometric parameters (Å, º) top

C1—C2	1.395 (3)	C12—N1	1.378 (2)
C1—C6	1.397 (3)	C12—C13	1.379 (3)
C1—C10	1.471 (3)	C13—C14	1.370 (3)
C2—C3	1.373 (3)	C13—H13	0.9300
C2—H2	0.9300	C14—H14	0.9300
C3—C4	1.369 (4)	C15—O3	1.219 (2)
C3—H3	0.9300	C15—N1	1.371 (2)
C4—C5	1.381 (3)	C15—N2	1.394 (2)
C4—H4	0.9300	C16—N1	1.459 (2)
C5—C6	1.387 (3)	C16—C17	1.466 (3)
C5—H5	0.9300	C16—H16A	0.9700
C6—C7	1.484 (3)	C16—H16B	0.9700
C7—O1	1.227 (2)	C17—C18	1.169 (3)
C7—C8	1.476 (2)	C18—H18	0.9300
C8—C11	1.406 (2)	C19—C20	1.456 (3)
C8—C9	1.421 (2)	C19—N2	1.473 (2)
C9—C14	1.390 (3)	C19—H19A	0.9700
C9—C10	1.484 (3)	C19—H19B	0.9700
C10—O2	1.229 (2)	C20—C21	1.171 (3)
C11—N2	1.405 (2)	C21—H21	0.9300
C11—C12	1.416 (2)

C2—C1—C6	119.6 (2)	N1—C12—C11	107.92 (16)
C2—C1—C10	120.4 (2)	C13—C12—C11	123.15 (18)
C6—C1—C10	120.03 (18)	C14—C13—C12	117.79 (17)
C3—C2—C1	120.3 (2)	C14—C13—H13	121.1
C3—C2—H2	119.9	C12—C13—H13	121.1
C1—C2—H2	119.9	C13—C14—C9	121.41 (18)
C4—C3—C2	120.2 (2)	C13—C14—H14	119.3
C4—C3—H3	119.9	C9—C14—H14	119.3
C2—C3—H3	119.9	O3—C15—N1	126.71 (18)
C3—C4—C5	120.5 (2)	O3—C15—N2	126.79 (18)
C3—C4—H4	119.8	N1—C15—N2	106.50 (16)
C5—C4—H4	119.8	N1—C16—C17	112.56 (15)
C4—C5—C6	120.4 (2)	N1—C16—H16A	109.1
C4—C5—H5	119.8	C17—C16—H16A	109.1
C6—C5—H5	119.8	N1—C16—H16B	109.1
C5—C6—C1	119.07 (19)	C17—C16—H16B	109.1
C5—C6—C7	119.76 (19)	H16A—C16—H16B	107.8
C1—C6—C7	121.15 (17)	C18—C17—C16	179.4 (3)
O1—C7—C8	120.95 (17)	C17—C18—H18	180.0
O1—C7—C6	119.40 (17)	C20—C19—N2	113.23 (15)
C8—C7—C6	119.51 (16)	C20—C19—H19A	108.9
C11—C8—C9	117.12 (15)	N2—C19—H19A	108.9
C11—C8—C7	124.07 (15)	C20—C19—H19B	108.9
C9—C8—C7	118.71 (16)	N2—C19—H19B	108.9
C14—C9—C8	121.60 (18)	H19A—C19—H19B	107.7
C14—C9—C10	117.17 (17)	C21—C20—C19	177.8 (2)
C8—C9—C10	121.23 (16)	C20—C21—H21	180.0
O2—C10—C1	120.4 (2)	C15—N1—C12	110.27 (15)
O2—C10—C9	120.58 (19)	C15—N1—C16	123.02 (17)
C1—C10—C9	118.97 (17)	C12—N1—C16	126.52 (17)
N2—C11—C8	135.60 (15)	C15—N2—C11	109.78 (14)
N2—C11—C12	105.52 (15)	C15—N2—C19	116.43 (15)
C8—C11—C12	118.87 (16)	C11—N2—C19	133.40 (14)
N1—C12—C13	128.92 (16)

C6—C1—C2—C3	0.3 (3)	C9—C8—C11—C12	2.0 (2)
C10—C1—C2—C3	178.5 (2)	C7—C8—C11—C12	−174.30 (15)
C1—C2—C3—C4	−1.4 (4)	N2—C11—C12—N1	0.18 (18)
C2—C3—C4—C5	1.2 (5)	C8—C11—C12—N1	179.18 (14)
C3—C4—C5—C6	0.1 (4)	N2—C11—C12—C13	−178.94 (15)
C4—C5—C6—C1	−1.3 (4)	C8—C11—C12—C13	0.1 (3)
C4—C5—C6—C7	177.0 (2)	N1—C12—C13—C14	179.16 (18)
C2—C1—C6—C5	1.0 (3)	C11—C12—C13—C14	−1.9 (3)
C10—C1—C6—C5	−177.15 (19)	C12—C13—C14—C9	1.7 (3)
C2—C1—C6—C7	−177.14 (18)	C8—C9—C14—C13	0.4 (3)
C10—C1—C6—C7	4.7 (3)	C10—C9—C14—C13	−179.65 (17)
C5—C6—C7—O1	−7.3 (3)	N1—C16—C17—C18	78 (22)
C1—C6—C7—O1	170.83 (18)	N2—C19—C20—C21	−169 (100)
C5—C6—C7—C8	176.98 (18)	O3—C15—N1—C12	−178.55 (18)
C1—C6—C7—C8	−4.8 (3)	N2—C15—N1—C12	0.87 (19)
O1—C7—C8—C11	5.9 (3)	O3—C15—N1—C16	6.1 (3)
C6—C7—C8—C11	−178.50 (16)	N2—C15—N1—C16	−174.45 (15)
O1—C7—C8—C9	−170.35 (17)	C13—C12—N1—C15	178.39 (17)
C6—C7—C8—C9	5.3 (2)	C11—C12—N1—C15	−0.67 (19)
C11—C8—C9—C14	−2.3 (2)	C13—C12—N1—C16	−6.5 (3)
C7—C8—C9—C14	174.22 (16)	C11—C12—N1—C16	174.46 (16)
C11—C8—C9—C10	177.82 (15)	C17—C16—N1—C15	−103.4 (2)
C7—C8—C9—C10	−5.7 (2)	C17—C16—N1—C12	82.1 (2)
C2—C1—C10—O2	−4.4 (3)	O3—C15—N2—C11	178.67 (17)
C6—C1—C10—O2	173.79 (18)	N1—C15—N2—C11	−0.75 (19)
C2—C1—C10—C9	176.93 (18)	O3—C15—N2—C19	−7.5 (3)
C6—C1—C10—C9	−4.9 (3)	N1—C15—N2—C19	173.08 (14)
C14—C9—C10—O2	6.9 (3)	C8—C11—N2—C15	−178.39 (18)
C8—C9—C10—O2	−173.18 (17)	C12—C11—N2—C15	0.35 (18)
C14—C9—C10—C1	−174.42 (16)	C8—C11—N2—C19	9.2 (3)
C8—C9—C10—C1	5.5 (3)	C12—C11—N2—C19	−172.03 (16)
C9—C8—C11—N2	−179.39 (17)	C20—C19—N2—C15	−105.30 (18)
C7—C8—C11—N2	4.3 (3)	C20—C19—N2—C11	66.7 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C18—H18···O2ⁱ	0.93	2.31	3.165 (3)	152
C21—H21···O1ⁱⁱ	0.93	2.38	3.275 (3)	161
C2—H2···O3ⁱⁱⁱ	0.93	2.62	3.333 (3)	134

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

Experimental details

Crystal data
Chemical formula	C₂₁H₁₂N₂O₃
M_r	340.33
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	296
a, b, c (Å)	16.6972 (5), 4.5602 (1), 21.2500 (5)
β (°)	96.352 (2)
V (Å³)	1608.10 (7)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.10
Crystal size (mm)	0.46 × 0.14 × 0.05

Data collection
Diffractometer	Bruker APEXII CCD diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	20426, 3177, 2301
R_int	0.033
(sin θ/λ)_max (Å⁻¹)	0.617

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.044, 0.129, 1.02
No. of reflections	3177
No. of parameters	235
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.33, −0.25

Computer programs: APEX2 (Bruker, 2009), SAINT-Plus (Bruker, 2009), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 2012), PLATON (Spek, 2009) and publCIF (Westrip, 2010).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C18—H18···O2ⁱ	0.93	2.31	3.165 (3)	152.0
C21—H21···O1ⁱⁱ	0.93	2.38	3.275 (3)	160.7
C2—H2···O3ⁱⁱⁱ	0.93	2.62	3.333 (3)	133.5

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

References

Afrakssou, Z., Kandri Rodi, Y., Capet, F., Essassi, E. M. & El Ammari, L. (2011). Acta Cryst. E67, o1253–o1254. Web of Science CSD CrossRef CAS IUCr Journals Google Scholar
Afrakssou, Z., Rodi, Y. K., Zouihri, H., Essassi, E. M. & Ng, S. W. (2010). Acta Cryst. E66, o1851. Web of Science CSD CrossRef IUCr Journals Google Scholar
Alves, D. S., Perez-Fons, L., Estepa, A. & Micol, V. (2004). Biochem. Pharmacol. 68, 549–561. Web of Science CrossRef PubMed CAS Google Scholar
Boseggia, E., Gatos, M., Lucatello, L., Mancin, F., Moro, S., Palumbo, M., Sissi, C., Tecilla, P., Tonellato, U. & Zagotto, G. (2004). J. Am. Chem. Soc. 126, 4543–4549. Web of Science CrossRef PubMed CAS Google Scholar
Bruker (2009). APEX2 and SAINT-Plus. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Ellis, L. T., Perkins, D. F., Turner, P. & Hambley, T. W. (2003). Dalton Trans. pp. 2728–2736. Web of Science CSD CrossRef Google Scholar
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849–854. Web of Science CrossRef CAS IUCr Journals Google Scholar
Guimarães, T. T., Da Silva Júnior, E. N., Carvalho, C. E. M., De Simone, C. A. & Pinto, A. V. (2009). Acta Cryst. E65, o1063. Web of Science CSD CrossRef IUCr Journals Google Scholar
Kadarkaraisamy, M., Caple, G., Gorden, A. R. & Sykes, A. G. (2008). Inorg. Chem. 47, 11644–11655. Web of Science CSD CrossRef PubMed CAS Google Scholar
Mariappan, K. & Basa, P. N. (2011). Inorg. Chim. Acta, 366, 344–349. Web of Science CSD CrossRef CAS Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920–925. Web of Science CrossRef CAS IUCr Journals Google Scholar

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 69| Part 6| June 2013| Page o944

doi:10.1107/S1600536813013688

Open

access