7-(4-Meth­oxy­phen­yl)-4,9-dimethyl-N-(4-methyl­phen­yl)-5,12-diaza­tetra­phen-6-amine

Vennila, K.N.; Prabha, K.; Prasad, K.J.R.; Velmurugan, D.

doi:10.1107/S1600536811006209

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 67| Part 4| April 2011| Pages o762-o763

doi:10.1107/S1600536811006209

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7-(4-Methoxyphenyl)-4,9-dimethyl-N-(4-methylphenyl)-5,12-diazatetraphen-6-amine

K. N. Vennila,^a K. Prabha,^b K. J. Rajendra Prasad ^b and D. Velmurugan ^a ^*

^aCentre of Advanced Study in Crystallography and Biophysics, University of Madras, Guindy Campus, Chennai 600 025, India, and ^bDepartment of Chemistry, Bharathiar University, Coimbatore 641 046, India
^*Correspondence e-mail: dvelmurugan@unom.ac.in

(Received 3 January 2011; accepted 18 February 2011; online 2 March 2011)

In the title compound, C₃₂H₂₇N₃O, the fused tetracycilc ring system is essentially planar [r.m.s. deviation = 0.07 (7) Å]. An intramolecular N—H⋯π(arene) interaction and a weak intramolecular C—H⋯N hydrogen bond may influence the molecular conformation. In the crystal, weak intermolecular C—H⋯N hydrogen bonds link the molecules into centrosymmetric dimers, forming R₂²(14) motifs. In addition, weak π–π stacking interactions with centroid–centroid distances in the range 3.578 (1)–3.739 (1) Å provide further stabilization.

Related literature

For the biological activity of naphthyridine derivatives, see: Gopalsamy et al. (2007 ); Kim et al. (2009 ); Nittoli et al. (2010 ); Bedard et al. (2000 ). For the structures of related naphthrydine derivatives, see: Peng et al. (2009 ); Seebacher et al . (2010); Vennila et al. (2010a ,b ). For standard bond lengths, see: Allen et al. (1987 ). For hydrogen-bond motifs, see: Bernstein et al. (1995 ).

Experimental

Crystal data

C₃₂H₂₇N₃O
M_r = 469.57
Monoclinic, P 2₁ /c
a = 8.3816 (6) Å
b = 23.1651 (13) Å
c = 12.8548 (7) Å
β = 91.171 (3)°
V = 2495.4 (3) Å³
Z = 4
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 293 K
0.29 × 0.24 × 0.23 mm

Data collection

Bruker SMART APEXII area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2004) T_min = 0.978, T_max = 0.983
24206 measured reflections
6239 independent reflections
3904 reflections with I > 2σ(I)
R_int = 0.029

Refinement

R[F² > 2σ(F²)] = 0.053
wR(F²) = 0.181
S = 0.95
6239 reflections
329 parameters
H-atom parameters constrained
Δρ_max = 0.27 e Å⁻³
Δρ_min = −0.23 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

Cg is the centroid of the C17–C22 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N3—H3⋯Cg	0.86	2.48	3.336 (3)	176
C28—H28⋯N1	0.93	2.37	2.927 (3)	118
C18—H18⋯N2ⁱ	0.93	2.55	3.435 (2)	159
Symmetry code: (i) -x+1, -y+1, -z.

Data collection: APEX2 (Bruker, 2007 ); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997 ); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811006209/lh5193sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811006209/lh5193Isup2.hkl

checkCIF report

Comment top

Dibenzo-naphthyridine analogs have been reported to be good Phosphoinositide-Dependent Kinase (PDK-1) inhibitors. Gopalsamy et al. (2007) and Kim et al. (2009) have described the synthesis and structure activity relationship analysis of a novel series of benzo[c][2,7]naphthyridines as potent PDK-1 inhibitors. Recently a few X-ray crystal structures of PDK-1 and dibenzo[2,7] naphthyridine analog complexes have been reported (Gopalsamy et al., 2007; Nittoli et al., 2010). A series of dibenzo-naphthyridines were sucessfully tested for anticancer assays (Gopalsamy et al., 2007; Nittoli et al., 2010). The naphthyridine compounds were also proven to exhibit potent activity against human cytomegalovirus (Bedard et al. , 2000). As we are focussing on heterocyclic naphthyridine derivatives with potential biological properties, the crystal structure of the title compound was determined.

The molecular structure of the title compound is shown in Fig. 1. The bond lengths and angles are in the normal ranges (Allen et al., 1987). The fused tetracyclic ring system is essentially planar in geometry as was previously reported for a related compounds (Vennila et al., 2010, 2011; Seebacher et al. 2010; Peng et al. 2009). An intramolecular N—H···π(arene) interaction and a weak intramolecular C—H···N hydrogen bond may influence the molecular conformation. In the crystal, weak intermolecular C—H···N hydrogen bonds link the molecules into centrosymmetric dimers forming R₂²(14) motifs (Bernstein et al., 1995) (see Fig. 2). In addition, weak π–π stacking interactions with centroid to centroid distances in the range 3.578 (1) - 3.739 (1) Å provide additional stabilization.

Related literature top

For the biological activity of naphthyridine derivatives, see: Gopalsamy et al. (2007); Kim et al. (2009); Nittoli et al. (2010); Bedard et al. (2000). For the structures of related naphthrydine derivatives, see: Peng et al. (2009); Seebacher et al . (2010); Vennila et al. (2010, 2011). For standard bond lengths, see: Allen et al. (1987). For hydrogen-bond motifs, see: Bernstein et al. (1995).

Experimental top

A mixture of 4',4''-dimethyl-2,4-bis-(N-phenylamino) quinoline (0.0010 mol) and p-methoxybenzoic acid (0.0011 mol) was added to polyphosphoric acid (3 g of P₂O₅ in 1.5 mL of H₃PO₄) and kept at 323-328K for 5 h. The reaction was monitored by TLC. After the completion of the reaction, the reaction mixture was poured into ice water and neutralised with saturated NaHCO₃ solution to remove the excess of p-methoxy benzoic acid. The precipitate was filtered, dried and purified by column chromatography over silica gel using petroleum ether : ethyl acetate (98 : 2). The product was recrystallised using ethyl acetate.

Computing details top

Data collection: APEX2 (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009).

Figures top

	Fig. 1. The molecular structure of the title compound, showing thermal ellipsoids drawn at 50% probability level.
	Fig. 2. The crystal packing of the title compound with hydrogen bonds shown as dashed lines.

7-(4-Methoxyphenyl)-4,9-dimethyl-N-(4-methylphenyl)-5,12- diazabenz[a]anthracen-6-amine top

Crystal data top

C₃₂H₂₇N₃O	F(000) = 992
M_r = 469.57	D_x = 1.250 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 6327 reflections
a = 8.3816 (6) Å	θ = 1.8–28.5°
b = 23.1651 (13) Å	µ = 0.08 mm⁻¹
c = 12.8548 (7) Å	T = 293 K
β = 91.171 (3)°	Block, yellow
V = 2495.4 (3) Å³	0.29 × 0.24 × 0.23 mm
Z = 4

Data collection top

Bruker SMART APEXII area-detector diffractometer	6239 independent reflections
Radiation source: fine-focus sealed tube	3904 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.029
ω and ϕ scans	θ_max = 28.5°, θ_min = 1.8°
Absorption correction: multi-scan (SADABS; Bruker, 2004)	h = −11→11
T_min = 0.978, T_max = 0.983	k = −29→30
24206 measured reflections	l = −17→16

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)] = 0.053	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.181	H-atom parameters constrained
S = 0.95	w = 1/[σ²(F_o²) + (0.0992P)² + 0.5542P] where P = (F_o² + 2F_c²)/3
6239 reflections	(Δ/σ)_max = 0.001
329 parameters	Δρ_max = 0.27 e Å⁻³
0 restraints	Δρ_min = −0.23 e Å⁻³

Crystal data top

C₃₂H₂₇N₃O	V = 2495.4 (3) Å³
M_r = 469.57	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 8.3816 (6) Å	µ = 0.08 mm⁻¹
b = 23.1651 (13) Å	T = 293 K
c = 12.8548 (7) Å	0.29 × 0.24 × 0.23 mm
β = 91.171 (3)°

Data collection top

Bruker SMART APEXII area-detector diffractometer	6239 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2004)	3904 reflections with I > 2σ(I)
T_min = 0.978, T_max = 0.983	R_int = 0.029
24206 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.053	0 restraints
wR(F²) = 0.181	H-atom parameters constrained
S = 0.95	Δρ_max = 0.27 e Å⁻³
6239 reflections	Δρ_min = −0.23 e Å⁻³
329 parameters

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.

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 > 2sigma(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
C11	0.27001 (18)	0.47982 (7)	0.01559 (12)	0.0415 (4)
N2	0.38310 (17)	0.54757 (6)	0.14162 (11)	0.0481 (3)
C9	0.44758 (19)	0.50366 (7)	0.19420 (12)	0.0437 (4)
C8	0.43129 (19)	0.44464 (7)	0.16148 (12)	0.0419 (4)
C17	0.29497 (18)	0.37335 (7)	0.03664 (12)	0.0416 (4)
C6	0.6097 (2)	0.47172 (8)	0.34423 (13)	0.0506 (4)
C10	0.29963 (19)	0.53681 (7)	0.05320 (13)	0.0452 (4)
C12	0.33652 (18)	0.43309 (6)	0.07278 (12)	0.0411 (4)
C7	0.52499 (19)	0.40261 (7)	0.22420 (12)	0.0445 (4)
C14	0.11930 (19)	0.51950 (8)	−0.13214 (13)	0.0488 (4)
N1	0.60278 (17)	0.41521 (6)	0.30973 (11)	0.0509 (4)
C13	0.1761 (2)	0.47325 (7)	−0.07674 (13)	0.0471 (4)
H13	0.1524	0.4362	−0.1004	0.056*
C5	0.5387 (2)	0.51709 (7)	0.28813 (13)	0.0508 (4)
N3	0.53552 (18)	0.34709 (6)	0.18772 (12)	0.0527 (4)
H3	0.4677	0.3388	0.1389	0.063*
C22	0.1889 (2)	0.34023 (7)	0.09339 (13)	0.0467 (4)
H22	0.1425	0.3560	0.1520	0.056*
O1	0.1768 (2)	0.20499 (5)	−0.04304 (11)	0.0739 (4)
C20	0.2205 (2)	0.26068 (7)	−0.02185 (14)	0.0523 (4)
C16	0.2387 (2)	0.58410 (7)	−0.00458 (15)	0.0534 (4)
H16	0.2565	0.6215	0.0194	0.064*
C19	0.3250 (2)	0.29293 (7)	−0.08088 (14)	0.0548 (5)
H19	0.3705	0.2770	−0.1397	0.066*
C18	0.3608 (2)	0.34901 (7)	−0.05119 (13)	0.0493 (4)
H18	0.4302	0.3707	−0.0909	0.059*
C15	0.1548 (2)	0.57559 (8)	−0.09457 (16)	0.0551 (5)
H15	0.1195	0.6074	−0.1326	0.066*
C23	0.6376 (2)	0.30140 (7)	0.21616 (14)	0.0517 (4)
C1	0.6987 (3)	0.48302 (9)	0.43698 (15)	0.0646 (5)
C21	0.1515 (2)	0.28481 (7)	0.06463 (14)	0.0529 (4)
H21	0.0798	0.2635	0.1033	0.063*
C33	0.0213 (2)	0.51229 (9)	−0.23006 (15)	0.0622 (5)
H33A	0.0461	0.4759	−0.2616	0.093*
H33B	0.0449	0.5430	−0.2774	0.093*
H33C	−0.0900	0.5133	−0.2139	0.093*
C4	0.5588 (3)	0.57407 (9)	0.32314 (16)	0.0680 (6)
H4	0.5125	0.6045	0.2861	0.082*
C26	0.8354 (2)	0.20560 (8)	0.25512 (18)	0.0661 (5)
C28	0.7225 (3)	0.29651 (9)	0.30897 (17)	0.0732 (6)
H28	0.7150	0.3250	0.3596	0.088*
C24	0.6517 (3)	0.25781 (8)	0.14459 (18)	0.0736 (6)
H24	0.5944	0.2600	0.0820	0.088*
C25	0.7489 (3)	0.21103 (9)	0.1638 (2)	0.0809 (7)
H25	0.7562	0.1823	0.1137	0.097*
C27	0.8194 (3)	0.24844 (10)	0.3259 (2)	0.0813 (7)
H27	0.8757	0.2456	0.3888	0.098*
C29	0.7759 (3)	0.43458 (11)	0.49655 (17)	0.0853 (7)
H29A	0.8283	0.4496	0.5579	0.128*
H29B	0.8529	0.4159	0.4537	0.128*
H29C	0.6961	0.4072	0.5162	0.128*
C2	0.7139 (3)	0.53922 (11)	0.46798 (18)	0.0831 (7)
H2	0.7713	0.5473	0.5289	0.100*
C30	0.9433 (3)	0.15394 (10)	0.2742 (2)	0.0919 (8)
H30A	1.0215	0.1521	0.2208	0.138*
H30B	0.8806	0.1193	0.2731	0.138*
H30C	0.9961	0.1578	0.3408	0.138*
C3	0.6470 (3)	0.58475 (11)	0.41220 (19)	0.0859 (7)
H3A	0.6619	0.6225	0.4351	0.103*
C32	0.2335 (5)	0.18004 (10)	−0.13340 (19)	0.1118 (11)
H32A	0.2088	0.2046	−0.1917	0.168*
H32B	0.1839	0.1431	−0.1439	0.168*
H32C	0.3470	0.1752	−0.1271	0.168*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C11	0.0348 (8)	0.0400 (8)	0.0498 (8)	−0.0001 (6)	0.0044 (7)	0.0023 (6)
N2	0.0441 (8)	0.0410 (7)	0.0595 (8)	−0.0014 (6)	0.0068 (7)	−0.0046 (6)
C9	0.0387 (8)	0.0436 (8)	0.0490 (9)	−0.0023 (7)	0.0078 (7)	−0.0036 (7)
C8	0.0372 (8)	0.0406 (8)	0.0480 (8)	−0.0009 (6)	0.0036 (7)	−0.0003 (6)
C17	0.0391 (8)	0.0385 (8)	0.0467 (8)	0.0003 (6)	−0.0060 (7)	0.0025 (6)
C6	0.0475 (10)	0.0572 (10)	0.0473 (9)	−0.0041 (8)	0.0044 (8)	−0.0061 (7)
C10	0.0363 (8)	0.0414 (8)	0.0582 (10)	−0.0002 (7)	0.0083 (7)	0.0000 (7)
C12	0.0359 (8)	0.0388 (8)	0.0488 (8)	0.0003 (6)	0.0045 (7)	0.0000 (6)
C7	0.0388 (8)	0.0462 (9)	0.0484 (9)	−0.0013 (7)	0.0007 (7)	0.0010 (7)
C14	0.0356 (8)	0.0539 (10)	0.0571 (10)	0.0041 (7)	0.0052 (7)	0.0107 (7)
N1	0.0479 (8)	0.0564 (9)	0.0483 (8)	−0.0009 (7)	−0.0005 (7)	−0.0016 (6)
C13	0.0409 (9)	0.0447 (9)	0.0557 (9)	0.0004 (7)	0.0028 (7)	0.0011 (7)
C5	0.0494 (10)	0.0535 (10)	0.0497 (9)	−0.0064 (8)	0.0061 (8)	−0.0097 (7)
N3	0.0519 (9)	0.0453 (8)	0.0603 (9)	0.0034 (6)	−0.0162 (7)	−0.0024 (6)
C22	0.0419 (9)	0.0458 (9)	0.0522 (9)	0.0014 (7)	−0.0011 (7)	0.0018 (7)
O1	0.1046 (12)	0.0424 (7)	0.0739 (9)	−0.0111 (7)	−0.0147 (8)	−0.0056 (6)
C20	0.0616 (11)	0.0377 (8)	0.0567 (10)	−0.0031 (7)	−0.0163 (8)	0.0017 (7)
C16	0.0444 (9)	0.0409 (9)	0.0751 (12)	0.0041 (7)	0.0066 (9)	0.0035 (8)
C19	0.0659 (12)	0.0489 (10)	0.0494 (9)	0.0032 (8)	−0.0044 (8)	−0.0061 (7)
C18	0.0534 (10)	0.0451 (9)	0.0496 (9)	−0.0033 (7)	0.0024 (8)	0.0002 (7)
C15	0.0403 (9)	0.0505 (10)	0.0746 (12)	0.0077 (8)	0.0063 (9)	0.0160 (8)
C23	0.0469 (10)	0.0455 (9)	0.0623 (10)	0.0013 (7)	−0.0075 (8)	0.0051 (8)
C1	0.0648 (13)	0.0780 (14)	0.0509 (10)	−0.0048 (10)	−0.0003 (9)	−0.0100 (9)
C21	0.0513 (10)	0.0452 (9)	0.0621 (10)	−0.0072 (8)	−0.0033 (8)	0.0074 (8)
C33	0.0490 (11)	0.0744 (13)	0.0630 (12)	0.0031 (9)	−0.0017 (9)	0.0145 (9)
C4	0.0821 (15)	0.0560 (11)	0.0660 (12)	−0.0063 (10)	0.0021 (11)	−0.0150 (9)
C26	0.0553 (12)	0.0505 (11)	0.0919 (15)	0.0047 (9)	−0.0111 (11)	0.0118 (10)
C28	0.0827 (15)	0.0653 (13)	0.0705 (13)	0.0191 (11)	−0.0235 (11)	−0.0045 (10)
C24	0.0892 (16)	0.0523 (11)	0.0778 (13)	0.0153 (10)	−0.0311 (12)	−0.0069 (10)
C25	0.0951 (18)	0.0512 (12)	0.0953 (16)	0.0183 (11)	−0.0236 (14)	−0.0100 (11)
C27	0.0821 (16)	0.0747 (14)	0.0857 (15)	0.0190 (12)	−0.0317 (13)	0.0073 (12)
C29	0.0919 (18)	0.1044 (19)	0.0587 (12)	0.0039 (14)	−0.0180 (12)	−0.0034 (12)
C2	0.0952 (19)	0.0912 (18)	0.0624 (13)	−0.0107 (14)	−0.0125 (12)	−0.0218 (12)
C30	0.0839 (17)	0.0659 (14)	0.125 (2)	0.0222 (12)	−0.0138 (15)	0.0159 (13)
C3	0.109 (2)	0.0742 (15)	0.0737 (14)	−0.0156 (14)	−0.0092 (14)	−0.0303 (12)
C32	0.209 (4)	0.0567 (14)	0.0696 (14)	−0.0158 (17)	−0.0010 (18)	−0.0162 (11)

Geometric parameters (Å, º) top

C11—C12	1.416 (2)	C19—H19	0.9300
C11—C13	1.419 (2)	C18—H18	0.9300
C11—C10	1.426 (2)	C15—H15	0.9300
N2—C9	1.330 (2)	C23—C24	1.373 (3)
N2—C10	1.346 (2)	C23—C28	1.381 (3)
C9—C8	1.436 (2)	C1—C2	1.367 (3)
C9—C5	1.449 (2)	C1—C29	1.498 (3)
C8—C12	1.402 (2)	C21—H21	0.9300
C8—C7	1.479 (2)	C33—H33A	0.9600
C17—C18	1.386 (2)	C33—H33B	0.9600
C17—C22	1.392 (2)	C33—H33C	0.9600
C17—C12	1.498 (2)	C4—C3	1.372 (3)
C6—N1	1.383 (2)	C4—H4	0.9300
C6—C5	1.400 (3)	C26—C27	1.355 (3)
C6—C1	1.418 (3)	C26—C25	1.373 (3)
C10—C16	1.413 (2)	C26—C30	1.517 (3)
C7—N1	1.300 (2)	C28—C27	1.393 (3)
C7—N3	1.372 (2)	C28—H28	0.9300
C14—C13	1.367 (2)	C24—C25	1.375 (3)
C14—C15	1.416 (3)	C24—H24	0.9300
C14—C33	1.498 (3)	C25—H25	0.9300
C13—H13	0.9300	C27—H27	0.9300
C5—C4	1.403 (2)	C29—H29A	0.9600
N3—C23	1.405 (2)	C29—H29B	0.9600
N3—H3	0.8600	C29—H29C	0.9600
C22—C21	1.371 (2)	C2—C3	1.387 (4)
C22—H22	0.9300	C2—H2	0.9300
O1—C20	1.367 (2)	C30—H30A	0.9600
O1—C32	1.390 (3)	C30—H30B	0.9600
C20—C19	1.388 (3)	C30—H30C	0.9600
C20—C21	1.381 (3)	C3—H3A	0.9300
C16—C15	1.356 (3)	C32—H32A	0.9600
C16—H16	0.9300	C32—H32B	0.9600
C19—C18	1.385 (2)	C32—H32C	0.9600

C12—C11—C13	123.91 (14)	C24—C23—C28	117.96 (17)
C12—C11—C10	117.89 (15)	C24—C23—N3	116.10 (16)
C13—C11—C10	118.20 (14)	C28—C23—N3	125.94 (17)
C9—N2—C10	119.11 (14)	C2—C1—C6	117.7 (2)
N2—C9—C8	122.97 (15)	C2—C1—C29	121.8 (2)
N2—C9—C5	117.45 (15)	C6—C1—C29	120.41 (19)
C8—C9—C5	119.59 (15)	C22—C21—C20	119.92 (16)
C12—C8—C9	117.95 (15)	C22—C21—H21	120.0
C12—C8—C7	127.10 (14)	C20—C21—H21	120.0
C9—C8—C7	114.88 (14)	C14—C33—H33A	109.5
C18—C17—C22	118.13 (15)	C14—C33—H33B	109.5
C18—C17—C12	122.29 (14)	H33A—C33—H33B	109.5
C22—C17—C12	119.57 (14)	C14—C33—H33C	109.5
N1—C6—C5	122.05 (16)	H33A—C33—H33C	109.5
N1—C6—C1	117.53 (17)	H33B—C33—H33C	109.5
C5—C6—C1	120.34 (17)	C3—C4—C5	119.7 (2)
N2—C10—C16	118.44 (15)	C3—C4—H4	120.1
N2—C10—C11	122.79 (15)	C5—C4—H4	120.1
C16—C10—C11	118.76 (16)	C27—C26—C25	116.68 (19)
C8—C12—C11	119.12 (14)	C27—C26—C30	122.4 (2)
C8—C12—C17	123.54 (14)	C25—C26—C30	120.9 (2)
C11—C12—C17	117.28 (14)	C23—C28—C27	119.3 (2)
N1—C7—N3	117.69 (15)	C23—C28—H28	120.4
N1—C7—C8	124.38 (15)	C27—C28—H28	120.4
N3—C7—C8	117.88 (15)	C23—C24—C25	121.2 (2)
C13—C14—C15	118.26 (17)	C23—C24—H24	119.4
C13—C14—C33	121.96 (17)	C25—C24—H24	119.4
C15—C14—C33	119.78 (16)	C26—C25—C24	121.8 (2)
C7—N1—C6	120.05 (15)	C26—C25—H25	119.1
C14—C13—C11	122.22 (16)	C24—C25—H25	119.1
C14—C13—H13	118.9	C26—C27—C28	123.1 (2)
C11—C13—H13	118.9	C26—C27—H27	118.5
C6—C5—C4	119.60 (17)	C28—C27—H27	118.5
C6—C5—C9	118.62 (15)	C1—C29—H29A	109.5
C4—C5—C9	121.78 (18)	C1—C29—H29B	109.5
C7—N3—C23	131.31 (15)	H29A—C29—H29B	109.5
C7—N3—H3	114.3	C1—C29—H29C	109.5
C23—N3—H3	114.3	H29A—C29—H29C	109.5
C21—C22—C17	121.33 (16)	H29B—C29—H29C	109.5
C21—C22—H22	119.3	C1—C2—C3	122.6 (2)
C17—C22—H22	119.3	C1—C2—H2	118.7
C20—O1—C32	117.64 (18)	C3—C2—H2	118.7
O1—C20—C19	124.64 (17)	C26—C30—H30A	109.5
O1—C20—C21	115.29 (16)	C26—C30—H30B	109.5
C19—C20—C21	120.07 (15)	H30A—C30—H30B	109.5
C15—C16—C10	120.74 (16)	C26—C30—H30C	109.5
C15—C16—H16	119.6	H30A—C30—H30C	109.5
C10—C16—H16	119.6	H30B—C30—H30C	109.5
C20—C19—C18	119.30 (16)	C4—C3—C2	119.9 (2)
C20—C19—H19	120.3	C4—C3—H3A	120.0
C18—C19—H19	120.3	C2—C3—H3A	120.0
C17—C18—C19	121.22 (16)	O1—C32—H32A	109.5
C17—C18—H18	119.4	O1—C32—H32B	109.5
C19—C18—H18	119.4	H32A—C32—H32B	109.5
C16—C15—C14	121.74 (16)	O1—C32—H32C	109.5
C16—C15—H15	119.1	H32A—C32—H32C	109.5
C14—C15—H15	119.1	H32B—C32—H32C	109.5

C10—N2—C9—C8	−0.6 (2)	C8—C9—C5—C4	179.71 (16)
C10—N2—C9—C5	179.02 (13)	N1—C7—N3—C23	−12.1 (3)
N2—C9—C8—C12	−3.1 (2)	C8—C7—N3—C23	165.47 (16)
C5—C9—C8—C12	177.28 (13)	C18—C17—C22—C21	0.9 (2)
N2—C9—C8—C7	174.06 (14)	C12—C17—C22—C21	−178.05 (15)
C5—C9—C8—C7	−5.5 (2)	C32—O1—C20—C19	−4.0 (3)
C9—N2—C10—C16	−176.83 (14)	C32—O1—C20—C21	175.4 (2)
C9—N2—C10—C11	3.3 (2)	N2—C10—C16—C15	179.56 (15)
C12—C11—C10—N2	−2.1 (2)	C11—C10—C16—C15	−0.5 (2)
C13—C11—C10—N2	177.95 (14)	O1—C20—C19—C18	−179.70 (17)
C12—C11—C10—C16	177.95 (14)	C21—C20—C19—C18	0.9 (3)
C13—C11—C10—C16	−2.0 (2)	C22—C17—C18—C19	−1.3 (3)
C9—C8—C12—C11	4.1 (2)	C12—C17—C18—C19	177.59 (16)
C7—C8—C12—C11	−172.70 (14)	C20—C19—C18—C17	0.4 (3)
C9—C8—C12—C17	−173.20 (14)	C10—C16—C15—C14	2.5 (3)
C7—C8—C12—C17	10.0 (2)	C13—C14—C15—C16	−1.9 (2)
C13—C11—C12—C8	178.23 (14)	C33—C14—C15—C16	177.88 (16)
C10—C11—C12—C8	−1.7 (2)	C7—N3—C23—C24	−160.3 (2)
C13—C11—C12—C17	−4.3 (2)	C7—N3—C23—C28	20.4 (3)
C10—C11—C12—C17	175.80 (13)	N1—C6—C1—C2	176.14 (18)
C18—C17—C12—C8	−107.91 (19)	C5—C6—C1—C2	−0.9 (3)
C22—C17—C12—C8	71.0 (2)	N1—C6—C1—C29	−2.4 (3)
C18—C17—C12—C11	74.7 (2)	C5—C6—C1—C29	−179.42 (18)
C22—C17—C12—C11	−106.41 (17)	C17—C22—C21—C20	0.5 (3)
C12—C8—C7—N1	−175.40 (15)	O1—C20—C21—C22	179.22 (16)
C9—C8—C7—N1	7.7 (2)	C19—C20—C21—C22	−1.4 (3)
C12—C8—C7—N3	7.2 (2)	C6—C5—C4—C3	−0.3 (3)
C9—C8—C7—N3	−169.75 (14)	C9—C5—C4—C3	−179.60 (19)
N3—C7—N1—C6	173.38 (15)	C24—C23—C28—C27	0.7 (3)
C8—C7—N1—C6	−4.1 (2)	N3—C23—C28—C27	−180.0 (2)
C5—C6—N1—C7	−1.9 (2)	C28—C23—C24—C25	−0.9 (3)
C1—C6—N1—C7	−178.88 (16)	N3—C23—C24—C25	179.7 (2)
C15—C14—C13—C11	−0.7 (2)	C27—C26—C25—C24	0.5 (4)
C33—C14—C13—C11	179.49 (14)	C30—C26—C25—C24	−179.3 (2)
C12—C11—C13—C14	−177.29 (15)	C23—C24—C25—C26	0.3 (4)
C10—C11—C13—C14	2.6 (2)	C25—C26—C27—C28	−0.7 (4)
N1—C6—C5—C4	−175.65 (17)	C30—C26—C27—C28	179.1 (2)
C1—C6—C5—C4	1.2 (3)	C23—C28—C27—C26	0.1 (4)
N1—C6—C5—C9	3.7 (2)	C6—C1—C2—C3	−0.4 (4)
C1—C6—C5—C9	−179.45 (15)	C29—C1—C2—C3	178.1 (2)
N2—C9—C5—C6	−179.17 (14)	C5—C4—C3—C2	−0.9 (4)
C8—C9—C5—C6	0.4 (2)	C1—C2—C3—C4	1.3 (4)
N2—C9—C5—C4	0.1 (2)

Hydrogen-bond geometry (Å, º) top

Cg is the centroid of the C17–C22 ring.

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3···Cg	0.86	2.48	3.336 (3)	176
C28—H28···N1	0.93	2.37	2.927 (3)	118
C18—H18···N2ⁱ	0.93	2.55	3.435 (2)	159

Symmetry code: (i) −x+1, −y+1, −z.

Experimental details

Crystal data
Chemical formula	C₃₂H₂₇N₃O
M_r	469.57
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	293
a, b, c (Å)	8.3816 (6), 23.1651 (13), 12.8548 (7)
β (°)	91.171 (3)
V (Å³)	2495.4 (3)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.08
Crystal size (mm)	0.29 × 0.24 × 0.23

Data collection
Diffractometer	Bruker SMART APEXII area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2004)
T_min, T_max	0.978, 0.983
No. of measured, independent and observed [I > 2σ(I)] reflections	24206, 6239, 3904
R_int	0.029
(sin θ/λ)_max (Å⁻¹)	0.671

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.053, 0.181, 0.95
No. of reflections	6239
No. of parameters	329
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.27, −0.23

Computer programs: APEX2 (Bruker, 2007), SAINT (Bruker, 2007), SHELXS97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997), SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

Cg is the centroid of the C17–C22 ring.

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3···Cg	0.86	2.48	3.336 (3)	176
C28—H28···N1	0.93	2.37	2.927 (3)	118
C18—H18···N2ⁱ	0.93	2.55	3.435 (2)	159

Symmetry code: (i) −x+1, −y+1, −z.

Acknowledgements

KNV thanks the CSIR, New Delhi, for financial assistance in the form of a Senior Research Fellowship. DV acknowledges the Department of Science and Technology (DST) for providing data-collection facilities under the TBI program and also thanks the DST for financial support under the UGC–SAP and DST–FIST programs.

References

Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1–19. CrossRef Web of Science Google Scholar
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Volume 67| Part 4| April 2011| Pages o762-o763

doi:10.1107/S1600536811006209

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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

7-(4-Meth­­oxy­phen­yl)-4,9-di­methyl-N-(4-methyl­phen­yl)-5,12-di­aza­tetra­phen-6-amine

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Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

7-(4-Methoxyphenyl)-4,9-dimethyl-N-(4-methylphenyl)-5,12-diazatetraphen-6-amine