N-(1-Naphth­yl)-10H-9-oxa-1,3-diaza­anthracen-4-amine

Fun, H.-K.; Chantrapromma, S.; Rai, S.; Shetty, P.; Isloor, A.M.

doi:10.1107/S1600536809004693

organic compounds

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ISSN: 2056-9890

Volume 65| Part 3| March 2009| Pages o523-o524

doi:10.1107/S1600536809004693

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N-(1-Naphthyl)-10H-9-oxa-1,3-diazaanthracen-4-amine

Hoong-Kun Fun,^a ^* Suchada Chantrapromma,^b ‡ Sankappa Rai,^c Prakash Shetty ^d and Arun M. Isloor ^e

^aX-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia, ^bCrystal Materials Research Unit, Department of Chemistry, Faculty of Science, Prince of Songkla University, Hat-Yai, Songkhla 90112, Thailand, ^cSyngene International Ltd, Biocon Park, Plot Nos. 2 and 3, Bommasandra 4th Phase, Jigani Link Road, Bangalore 560 100, India, ^dDepartment of Printing, Manipal Institute of Technology, Manipal 576 104, India, and ^eDepartment of Chemistry, National Institute of Technology-Karnataka, Surathkal, Mangalore 575 025, India
^*Correspondence e-mail: hkfun@usm.my

(Received 4 February 2009; accepted 9 February 2009; online 13 February 2009)

In the molecule of the title compound, C₂₁H₁₅N₃O, the 10H-9-oxa-1,3-diazaanthracene ring system is slightly bent, with dihedral angles of 3.99 (6) and 4.80 (6)° between the pyran ring and the pyrimidine and benzene rings, respectively. This ring system makes a dihedral angle of 85.23 (3)° with the naphthalene plane. In the crystal packing, molecules are linked by N—H⋯N hydrogen bonds into chains along the a axis and these chains are stacked along the b axis. The crystal is further stabilized by weak C—H⋯N and C—H⋯π interactions.

Related literature

For values of bond lengths, see Allen et al. (1987 ). For background to the bioactivity and applications of naphthyrimidines, see, for example: Bedard et al. (2000 ); Bohme & Haake (1976 ); Erian (1993 ); Falardeau et al. (2000 ); Martinez & Marco (1997 ); Tandon et al. (1991 ); Taylor & McKillop (1970 ). For the stability of the temperature controller, see Cosier & Glazer (1986 ).

Experimental

Crystal data

C₂₁H₁₅N₃O
M_r = 325.36
Orthorhombic, P b c a
a = 13.2762 (3) Å
b = 8.8700 (2) Å
c = 27.1997 (5) Å
V = 3203.03 (12) Å³
Z = 8
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 100 K
0.57 × 0.38 × 0.03 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2005 ) T_min = 0.901, T_max = 0.997
27104 measured reflections
4673 independent reflections
3649 reflections with I > 2σ(I)
R_int = 0.042

Refinement

R[F² > 2σ(F²)] = 0.045
wR(F²) = 0.142
S = 1.08
4673 reflections
230 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.35 e Å⁻³
Δρ_min = −0.33 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 and Cg2 are the centroids of the C1–C3/C11/N1/N2 and C4–C9 rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N3—H1N3⋯N2ⁱ	0.913 (16)	2.143 (16)	2.9722 (13)	150.6 (14)
C13—H13A⋯N2ⁱⁱ	0.93	2.62	3.4791 (16)	154
C20—H20A⋯N3	0.93	2.60	2.9077 (15)	100
C20—H20A⋯N1ⁱⁱⁱ	0.93	2.48	3.3232 (17)	150
C10—H10A⋯Cg1ⁱⁱⁱ	0.97	2.76	3.5855 (14)	143
C10—H10B⋯Cg2ⁱⁱ	0.97	2.96	3.6792 (14)	132
C13—H13A⋯Cg1ⁱⁱ	0.93	2.63	3.3503 (14)	135
Symmetry codes: (i) $[x+{\script{1\over 2}}, y, -z+{\script{1\over 2}}]$ ; (ii) $[-x+{\script{1\over 2}}, y+{\script{1\over 2}}, z]$ ; (iii) $[-x+{\script{1\over 2}}, y-{\script{1\over 2}}, z]$ .

Data collection: APEX2 (Bruker, 2005); cell refinement: APEX2; data reduction: SAINT (Bruker, 2005); program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2003 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809004693/sj2571sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809004693/sj2571Isup2.hkl

checkCIF report

Comment top

Condensed heterocyclic systems are of considerable interest not only because of their potential biological activity but also because of their versatility as synthons in organic transformations (Bohme & Haake, 1976; Taylor & McKillop, 1970; Erian, 1993). A series of 1,6-naphthyrimidines have been demonstrated to possess antihuman cytomegalovirus (HCMV) activity (Falardeau et al., 2000; Bedard et al., 2000). Furthermore, chromenes and their fused heterocyclic derivatives have attracted a great deal of interest due to their wide applications in the field of pharmaceuticals (Martinez & Marco, 1997; Tandon et al., 1991). In view of these observations, we have synthesized title compound which is a new chromenopyrimidine molecule and its crystal structure was reported here.

In the structure of the title compound (I) (Fig. 1), the 10H-9-oxa-1,3-diaza-anthracene ring system is slightly bent as indicated by the dihedral angles between the central ring and the two side rings being 3.99 (6)° (for the C1–C3/C11/N1–N2 ring) and 4.80 (6)° (for the C4–C9 ring). The naphthalene ring system is planar with the largest deviation 0.027 (1) Å for atom C9. The 10H-9-oxa-1,3-diaza-anthracene ring is almost perpendicular with the naphthalene ring as shown by the dihedral angle between these two ring systems being 83.00 (15)°. The naphthalene–amine moiety (N3/C12–C21) is in (+)-syn-clinal with respect to the C1–C3/C11/N1–N2 ring with a torsion angle C1—N3—C12–C21 = 83.00 (15)°. The bond distances have normal values (Allen et al., 1987).

In the crystal packing, N—H···N hydrogen bonds (Table 1, Fig. 2) link the molecules into chains along the a axis and these molecular chains are stacked along the b axis. The crystal is further stabilized by weak C—H···N and C—H···π interactions; Cg1 and Cg2 are the centroids of C1–C3/C11/N1–N2 and C4–C9 rings, respectively (Table 1).

Related literature top

For values of bond lengths, see Allen et al. (1987). For background to the bioactivity and applications of naphthyrimidines, see, for example: Bedard et al. (2000); Bohme & Haake (1976); Erian (1993); Falardeau et al. (2000); Martinez & Marco (1997); Tandon et al. (1991); Taylor & McKillop (1970). For stability of temperature controller, see Cosier & Glazer (1986).

Experimental top

The title compound was obtained by vigorously stirring a solution of 2-amino-4H-chromene-3-carbonitrile 0.5 g (2.8 mmol) in 10 ml of dimethyl formamide dimethylacetal which has been heated to reflux for 2 h. Excess dimethyl formamide dimethyl acetal was removed and the residue obtained was dissolved in acetic acid (10 ml). Amine 0.41 g (2.8 mmol) was then added and heated to reflux for an additional 2 h. The reaction mixture was concentrated and finally the residue was purified by column chromatography using petroleum ether–ethyl acetate (60:40 v/v) to get desired compound as a crystalline solid 0.59 g (Yield 63%, m.p. 513–515 K).

Computing details top

Data collection: APEX2 (Bruker, 2005); cell refinement: APEX2 (Bruker, 2005); data reduction: SAINT (Bruker, 2005); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2003).

Figures top

	Fig. 1. The structure of (I), showing 50% probability displacement ellipsoids and the atom-numbering scheme.
	Fig. 2. The packing diagram of (I), viewed along the b axis, showing molecular chains along the a axis. Hydrogen bonds are shown as dashed lines.

N-(1-Naphthyl)-10H-9-oxa-1,3-diazaanthracen-4-amine top

Crystal data top

C₂₁H₁₅N₃O	D_x = 1.349 Mg m⁻³
M_r = 325.36	Melting point = 513–515 K
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 4673 reflections
a = 13.2762 (3) Å	θ = 1.5–30.0°
b = 8.8700 (2) Å	µ = 0.09 mm⁻¹
c = 27.1997 (5) Å	T = 100 K
V = 3203.03 (12) Å³	Plate, colourless
Z = 8	0.57 × 0.38 × 0.03 mm
F(000) = 1360

Data collection top

Bruker SMART APEXII CCD area-detector diffractometer	4673 independent reflections
Radiation source: fine-focus sealed tube	3649 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.042
Detector resolution: 8.33 pixels mm^-1	θ_max = 30.0°, θ_min = 1.5°
ω scans	h = −18→18
Absorption correction: multi-scan (SADABS; Bruker, 2005)	k = −12→12
T_min = 0.901, T_max = 0.997	l = −37→38
27104 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)] = 0.045	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.142	H atoms treated by a mixture of independent and constrained refinement
S = 1.08	w = 1/[σ²(F_o²) + (0.0844P)² + 0.3525P] where P = (F_o² + 2F_c²)/3
4673 reflections	(Δ/σ)_max = 0.001
230 parameters	Δρ_max = 0.35 e Å⁻³
0 restraints	Δρ_min = −0.33 e Å⁻³

Crystal data top

C₂₁H₁₅N₃O	V = 3203.03 (12) Å³
M_r = 325.36	Z = 8
Orthorhombic, Pbca	Mo Kα radiation
a = 13.2762 (3) Å	µ = 0.09 mm⁻¹
b = 8.8700 (2) Å	T = 100 K
c = 27.1997 (5) Å	0.57 × 0.38 × 0.03 mm

Data collection top

Bruker SMART APEXII CCD area-detector diffractometer	4673 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2005)	3649 reflections with I > 2σ(I)
T_min = 0.901, T_max = 0.997	R_int = 0.042
27104 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.045	0 restraints
wR(F²) = 0.142	H atoms treated by a mixture of independent and constrained refinement
S = 1.08	Δρ_max = 0.35 e Å⁻³
4673 reflections	Δρ_min = −0.33 e Å⁻³
230 parameters

Special details top

Experimental. The crystal was placed in the cold stream of an Oxford Cryosystems Cobra open-flow nitrogen cryostat (Cosier & Glazer, 1986) operating at 100.0 (1) K.

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
O1	0.08414 (6)	0.31457 (10)	0.18202 (3)	0.0193 (2)
N1	0.18466 (7)	0.51429 (12)	0.30718 (4)	0.0183 (2)
N2	0.05453 (7)	0.44680 (12)	0.25056 (3)	0.0180 (2)
N3	0.35056 (7)	0.44664 (13)	0.29448 (3)	0.0182 (2)
H1N3	0.4016 (12)	0.4226 (19)	0.2734 (6)	0.034 (4)*
C1	0.25345 (8)	0.44337 (14)	0.27880 (4)	0.0156 (2)
C2	0.09044 (9)	0.51210 (15)	0.29118 (4)	0.0184 (2)
H2A	0.0435	0.5622	0.3106	0.022*
C3	0.12498 (8)	0.37767 (14)	0.22322 (4)	0.0163 (2)
C4	0.14513 (9)	0.22381 (14)	0.15270 (4)	0.0174 (2)
C5	0.09574 (9)	0.15384 (16)	0.11364 (4)	0.0220 (3)
H5A	0.0277	0.1716	0.1081	0.026*
C6	0.14946 (10)	0.05735 (16)	0.08316 (4)	0.0245 (3)
H6A	0.1175	0.0100	0.0569	0.029*
C7	0.25153 (10)	0.03159 (16)	0.09199 (4)	0.0234 (3)
H7A	0.2873	−0.0352	0.0723	0.028*
C8	0.29956 (9)	0.10591 (15)	0.13028 (4)	0.0202 (3)
H8A	0.3679	0.0893	0.1355	0.024*
C9	0.24765 (8)	0.20522 (14)	0.16123 (4)	0.0169 (2)
C10	0.30044 (8)	0.29292 (15)	0.20116 (4)	0.0178 (2)
H10A	0.3420	0.2249	0.2204	0.021*
H10B	0.3442	0.3677	0.1863	0.021*
C11	0.22622 (8)	0.37036 (14)	0.23449 (4)	0.0156 (2)
C12	0.37886 (8)	0.52034 (15)	0.33935 (4)	0.0175 (2)
C13	0.41910 (9)	0.66208 (16)	0.33759 (4)	0.0218 (3)
H13A	0.4274	0.7097	0.3074	0.026*
C14	0.44831 (10)	0.73748 (16)	0.38139 (5)	0.0247 (3)
H14A	0.4748	0.8344	0.3798	0.030*
C15	0.43757 (9)	0.66800 (16)	0.42576 (5)	0.0240 (3)
H15A	0.4560	0.7185	0.4543	0.029*
C16	0.39841 (9)	0.51891 (16)	0.42882 (4)	0.0210 (3)
C17	0.38629 (10)	0.44401 (18)	0.47457 (4)	0.0273 (3)
H17A	0.4035	0.4937	0.5035	0.033*
C18	0.34979 (10)	0.30001 (19)	0.47687 (5)	0.0310 (3)
H18A	0.3425	0.2527	0.5072	0.037*
C19	0.32313 (10)	0.22321 (18)	0.43346 (5)	0.0272 (3)
H19A	0.3001	0.1243	0.4352	0.033*
C20	0.33080 (9)	0.29311 (16)	0.38844 (4)	0.0215 (3)
H20A	0.3113	0.2422	0.3601	0.026*
C21	0.36831 (8)	0.44257 (15)	0.38505 (4)	0.0179 (2)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0145 (4)	0.0257 (5)	0.0178 (4)	0.0017 (3)	−0.0020 (3)	−0.0046 (3)
N1	0.0160 (5)	0.0215 (5)	0.0175 (4)	0.0021 (4)	0.0008 (3)	−0.0018 (4)
N2	0.0145 (4)	0.0211 (5)	0.0183 (4)	0.0019 (4)	−0.0010 (3)	0.0001 (4)
N3	0.0128 (4)	0.0267 (6)	0.0152 (4)	0.0008 (4)	−0.0012 (3)	−0.0035 (4)
C1	0.0141 (5)	0.0170 (6)	0.0156 (4)	0.0002 (4)	−0.0003 (4)	0.0016 (4)
C2	0.0163 (5)	0.0212 (6)	0.0178 (5)	0.0019 (5)	0.0020 (4)	−0.0005 (4)
C3	0.0167 (5)	0.0181 (6)	0.0141 (4)	0.0002 (5)	−0.0002 (4)	0.0009 (4)
C4	0.0174 (5)	0.0189 (6)	0.0158 (5)	−0.0008 (5)	0.0009 (4)	0.0005 (4)
C5	0.0202 (6)	0.0272 (7)	0.0186 (5)	−0.0035 (5)	−0.0012 (4)	0.0005 (5)
C6	0.0279 (6)	0.0277 (7)	0.0178 (5)	−0.0051 (5)	−0.0005 (4)	−0.0030 (5)
C7	0.0279 (6)	0.0238 (7)	0.0185 (5)	−0.0003 (5)	0.0052 (5)	−0.0019 (5)
C8	0.0205 (5)	0.0217 (6)	0.0182 (5)	0.0016 (5)	0.0033 (4)	0.0015 (5)
C9	0.0183 (5)	0.0177 (6)	0.0148 (4)	−0.0004 (4)	0.0011 (4)	0.0009 (4)
C10	0.0138 (5)	0.0225 (6)	0.0171 (5)	0.0012 (4)	0.0001 (4)	−0.0019 (4)
C11	0.0152 (5)	0.0173 (6)	0.0144 (4)	0.0008 (4)	−0.0001 (4)	0.0006 (4)
C12	0.0131 (5)	0.0227 (6)	0.0167 (5)	0.0023 (4)	−0.0006 (4)	−0.0028 (4)
C13	0.0198 (6)	0.0243 (7)	0.0213 (5)	0.0001 (5)	−0.0028 (4)	0.0021 (5)
C14	0.0228 (6)	0.0215 (6)	0.0297 (6)	−0.0039 (5)	−0.0053 (5)	−0.0025 (5)
C15	0.0211 (6)	0.0282 (7)	0.0227 (5)	−0.0001 (5)	−0.0047 (4)	−0.0069 (5)
C16	0.0160 (5)	0.0288 (7)	0.0183 (5)	0.0003 (5)	−0.0015 (4)	−0.0033 (5)
C17	0.0223 (6)	0.0427 (9)	0.0169 (5)	−0.0020 (6)	−0.0022 (4)	−0.0014 (5)
C18	0.0262 (6)	0.0453 (9)	0.0214 (6)	−0.0048 (6)	−0.0008 (5)	0.0080 (6)
C19	0.0220 (6)	0.0311 (8)	0.0285 (6)	−0.0060 (6)	−0.0003 (5)	0.0049 (6)
C20	0.0173 (5)	0.0252 (7)	0.0218 (5)	−0.0017 (5)	−0.0003 (4)	−0.0016 (5)
C21	0.0128 (5)	0.0233 (6)	0.0176 (5)	0.0019 (5)	−0.0007 (4)	−0.0026 (5)

Geometric parameters (Å, º) top

O1—C3	1.3649 (13)	C9—C10	1.5085 (16)
O1—C4	1.3927 (14)	C10—C11	1.5050 (15)
N1—C2	1.3245 (15)	C10—H10A	0.9700
N1—C1	1.3511 (14)	C10—H10B	0.9700
N2—C2	1.3355 (15)	C12—C13	1.3669 (19)
N2—C3	1.3432 (15)	C12—C21	1.4287 (16)
N3—C1	1.3582 (14)	C13—C14	1.4202 (17)
N3—C12	1.4345 (14)	C13—H13A	0.9300
N3—H1N3	0.913 (17)	C14—C15	1.3626 (18)
C1—C11	1.4151 (15)	C14—H14A	0.9300
C2—H2A	0.9300	C15—C16	1.4234 (19)
C3—C11	1.3800 (15)	C15—H15A	0.9300
C4—C9	1.3905 (16)	C16—C17	1.4198 (17)
C4—C5	1.3943 (16)	C16—C21	1.4266 (16)
C5—C6	1.3886 (18)	C17—C18	1.368 (2)
C5—H5A	0.9300	C17—H17A	0.9300
C6—C7	1.3951 (19)	C18—C19	1.4082 (19)
C6—H6A	0.9300	C18—H18A	0.9300
C7—C8	1.3878 (17)	C19—C20	1.3764 (17)
C7—H7A	0.9300	C19—H19A	0.9300
C8—C9	1.3999 (16)	C20—C21	1.4191 (19)
C8—H8A	0.9300	C20—H20A	0.9300

C3—O1—C4	118.43 (9)	C11—C10—H10B	109.3
C2—N1—C1	116.35 (10)	C9—C10—H10B	109.3
C2—N2—C3	114.05 (10)	H10A—C10—H10B	108.0
C1—N3—C12	121.70 (10)	C3—C11—C1	114.62 (10)
C1—N3—H1N3	120.1 (10)	C3—C11—C10	121.68 (10)
C12—N3—H1N3	116.5 (10)	C1—C11—C10	123.68 (10)
N1—C1—N3	116.89 (10)	C13—C12—C21	120.85 (11)
N1—C1—C11	121.79 (10)	C13—C12—N3	119.46 (11)
N3—C1—C11	121.31 (10)	C21—C12—N3	119.64 (11)
N1—C2—N2	127.97 (11)	C12—C13—C14	120.70 (11)
N1—C2—H2A	116.0	C12—C13—H13A	119.6
N2—C2—H2A	116.0	C14—C13—H13A	119.6
N2—C3—O1	111.42 (9)	C15—C14—C13	120.09 (12)
N2—C3—C11	125.21 (10)	C15—C14—H14A	120.0
O1—C3—C11	123.37 (10)	C13—C14—H14A	120.0
C9—C4—O1	122.82 (10)	C14—C15—C16	120.68 (11)
C9—C4—C5	122.33 (11)	C14—C15—H15A	119.7
O1—C4—C5	114.85 (10)	C16—C15—H15A	119.7
C6—C5—C4	119.18 (11)	C17—C16—C15	121.83 (11)
C6—C5—H5A	120.4	C17—C16—C21	118.52 (12)
C4—C5—H5A	120.4	C15—C16—C21	119.64 (11)
C5—C6—C7	119.81 (11)	C18—C17—C16	121.15 (12)
C5—C6—H6A	120.1	C18—C17—H17A	119.4
C7—C6—H6A	120.1	C16—C17—H17A	119.4
C8—C7—C6	119.84 (12)	C17—C18—C19	120.17 (12)
C8—C7—H7A	120.1	C17—C18—H18A	119.9
C6—C7—H7A	120.1	C19—C18—H18A	119.9
C7—C8—C9	121.60 (11)	C20—C19—C18	120.62 (14)
C7—C8—H8A	119.2	C20—C19—H19A	119.7
C9—C8—H8A	119.2	C18—C19—H19A	119.7
C4—C9—C8	117.14 (10)	C19—C20—C21	120.30 (12)
C4—C9—C10	120.92 (10)	C19—C20—H20A	119.8
C8—C9—C10	121.91 (10)	C21—C20—H20A	119.8
C11—C10—C9	111.40 (9)	C20—C21—C16	119.18 (11)
C11—C10—H10A	109.3	C20—C21—C12	122.82 (11)
C9—C10—H10A	109.3	C16—C21—C12	118.00 (11)

C2—N1—C1—N3	179.12 (11)	N1—C1—C11—C3	−0.19 (17)
C2—N1—C1—C11	−0.19 (17)	N3—C1—C11—C3	−179.46 (11)
C12—N3—C1—N1	0.71 (17)	N1—C1—C11—C10	178.62 (11)
C12—N3—C1—C11	−179.98 (11)	N3—C1—C11—C10	−0.66 (18)
C1—N1—C2—N2	0.81 (19)	C9—C10—C11—C3	−10.17 (16)
C3—N2—C2—N1	−0.92 (19)	C9—C10—C11—C1	171.11 (11)
C2—N2—C3—O1	−179.33 (10)	C1—N3—C12—C13	−99.41 (14)
C2—N2—C3—C11	0.44 (18)	C1—N3—C12—C21	83.00 (15)
C4—O1—C3—N2	−172.67 (10)	C21—C12—C13—C14	−2.11 (18)
C4—O1—C3—C11	7.55 (17)	N3—C12—C13—C14	−179.66 (11)
C3—O1—C4—C9	−5.68 (16)	C12—C13—C14—C15	0.8 (2)
C3—O1—C4—C5	174.98 (11)	C13—C14—C15—C16	0.9 (2)
C9—C4—C5—C6	2.60 (19)	C14—C15—C16—C17	−179.90 (12)
O1—C4—C5—C6	−178.05 (11)	C14—C15—C16—C21	−1.21 (18)
C4—C5—C6—C7	0.09 (19)	C15—C16—C17—C18	−179.14 (12)
C5—C6—C7—C8	−1.9 (2)	C21—C16—C17—C18	2.15 (19)
C6—C7—C8—C9	1.13 (19)	C16—C17—C18—C19	−0.2 (2)
O1—C4—C9—C8	177.40 (11)	C17—C18—C19—C20	−1.8 (2)
C5—C4—C9—C8	−3.31 (18)	C18—C19—C20—C21	1.7 (2)
O1—C4—C9—C10	−4.59 (17)	C19—C20—C21—C16	0.33 (18)
C5—C4—C9—C10	174.71 (11)	C19—C20—C21—C12	179.40 (12)
C7—C8—C9—C4	1.42 (18)	C17—C16—C21—C20	−2.21 (17)
C7—C8—C9—C10	−176.57 (12)	C15—C16—C21—C20	179.06 (11)
C4—C9—C10—C11	11.79 (16)	C17—C16—C21—C12	178.68 (11)
C8—C9—C10—C11	−170.29 (11)	C15—C16—C21—C12	−0.06 (17)
N2—C3—C11—C1	0.05 (18)	C13—C12—C21—C20	−177.38 (11)
O1—C3—C11—C1	179.80 (10)	N3—C12—C21—C20	0.17 (17)
N2—C3—C11—C10	−178.78 (11)	C13—C12—C21—C16	1.70 (17)
O1—C3—C11—C10	0.97 (18)	N3—C12—C21—C16	179.25 (10)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N3—H1N3···N2ⁱ	0.913 (16)	2.143 (16)	2.9722 (13)	150.6 (14)
C13—H13A···N2ⁱⁱ	0.93	2.62	3.4791 (16)	154
C20—H20A···N3	0.93	2.60	2.9077 (15)	100
C20—H20A···N1ⁱⁱⁱ	0.93	2.48	3.3232 (17)	150
C10—H10A···Cg1ⁱⁱⁱ	0.97	2.76	3.5855 (14)	143
C10—H10B···Cg2ⁱⁱ	0.97	2.96	3.6792 (14)	132
C13—H13A···Cg1ⁱⁱ	0.93	2.63	3.3503 (14)	135

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

Experimental details

Crystal data
Chemical formula	C₂₁H₁₅N₃O
M_r	325.36
Crystal system, space group	Orthorhombic, Pbca
Temperature (K)	100
a, b, c (Å)	13.2762 (3), 8.8700 (2), 27.1997 (5)
V (Å³)	3203.03 (12)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.57 × 0.38 × 0.03

Data collection
Diffractometer	Bruker SMART APEXII CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2005)
T_min, T_max	0.901, 0.997
No. of measured, independent and observed [I > 2σ(I)] reflections	27104, 4673, 3649
R_int	0.042
(sin θ/λ)_max (Å⁻¹)	0.703

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.045, 0.142, 1.08
No. of reflections	4673
No. of parameters	230
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.35, −0.33

Computer programs: APEX2 (Bruker, 2005), SAINT (Bruker, 2005), SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2003).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N3—H1N3···N2ⁱ	0.913 (16)	2.143 (16)	2.9722 (13)	150.6 (14)
C13—H13A···N2ⁱⁱ	0.93	2.62	3.4791 (16)	154
C20—H20A···N3	0.93	2.60	2.9077 (15)	100
C20—H20A···N1ⁱⁱⁱ	0.93	2.48	3.3232 (17)	150
C10—H10A···Cg1ⁱⁱⁱ	0.97	2.76	3.5855 (14)	143
C10—H10B···Cg2ⁱⁱ	0.97	2.96	3.6792 (14)	132
C13—H13A···Cg1ⁱⁱ	0.93	2.63	3.3503 (14)	135

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

Footnotes

‡Additional correspondence author, e-mail: suchada.c@psu.ac.th.

Acknowledgements

AMI is grateful to the Director, NITK, Surathkal, India, for providing research facilities. SR thanks Dr Gautam Das, Syngene International Ltd, Bangalore, India, for allocation of research resources. The authors also thank the Universiti Sains Malaysia for Research University Golden Goose Grant No. 1001/PFIZIK/811012.

References

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