N-{(E)-[4-(Dimethyl­amino)­phen­yl]methyl­idene}-2,3-dimethyl­aniline

Sarfraz, M.; Tariq, M.I.; Tahir, M.N.

doi:10.1107/S1600536810027832

organic compounds

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ISSN: 2056-9890

Volume 66| Part 8| August 2010| Page o2055

https://doi.org/10.1107/S1600536810027832

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N-{(E)-[4-(Dimethylamino)phenyl]methylidene}-2,3-dimethylaniline

Muhammad Sarfraz,^a Muhammad Ilyas Tariq ^a and M. Nawaz Tahir ^b ^*

^aDepartment of Chemistry, University of Sargodha, Sargodha, Pakistan, and ^bDepartment of Physics, University of Sargodha, Sargodha, Pakistan
^*Correspondence e-mail: dmntahir_uos@yahoo.com

(Received 11 July 2010; accepted 13 July 2010; online 17 July 2010)

There are two independent molecules in the asymmetric unit of the title compound, C₁₇H₂₀N₂, in which the dihedral angles between the aromatic rings are 30.34 (11) and 41.44 (8)°. In the crystal, weak C—H⋯π interactions may help to establish the packing.

Related literature

For related structures, see: Hussain et al. (2010 ); Tahir et al. (2010a ,b ); Tariq et al. (2010 ).

Experimental

Crystal data

C₁₇H₂₀N₂
M_r = 252.35
Triclinic, $[P \overline 1]$
a = 7.6556 (8) Å
b = 7.7296 (8) Å
c = 25.059 (3) Å
α = 93.843 (6)°
β = 95.436 (6)°
γ = 97.431 (5)°
V = 1459.1 (3) Å³
Z = 4
Mo Kα radiation
μ = 0.07 mm⁻¹
T = 296 K
0.28 × 0.18 × 0.16 mm

Data collection

Bruker Kappa APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2005 ) T_min = 0.982, T_max = 0.988
20871 measured reflections
5142 independent reflections
2482 reflections with I > 2σ(I)
R_int = 0.075

Refinement

R[F² > 2σ(F²)] = 0.065
wR(F²) = 0.188
S = 1.02
5142 reflections
352 parameters
H-atom parameters constrained
Δρ_max = 0.49 e Å⁻³
Δρ_min = −0.50 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

Cg1, Cg2 and Cg4 are the centroids of the C1–C6, C10–C15 and C27–C32 benzene rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C7—H7A⋯Cg1ⁱ	0.96	2.90	3.756 (3)	149
C16—H16C⋯Cg4ⁱⁱ	0.96	2.69	3.434 (4)	135
C32—H32⋯Cg2ⁱⁱⁱ	0.93	2.88	3.698 (3)	148
Symmetry codes: (i) -x+1, -y, -z+1; (ii) x+1, y-1, z; (iii) x, y+1, z.

Data collection: APEX2 (Bruker, 2009 ); cell refinement: SAINT (Bruker, 2009); 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 ) and PLATON (Spek, 2009 ); software used to prepare material for publication: WinGX (Farrugia, 1999 ) and PLATON.

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S1600536810027832/hb5549sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810027832/hb5549Isup2.hkl

checkCIF report

Comment top

The title compound (I, Fig. 1) is being reported in continuation to synthesize various Schiff bases (Hussain et al., 2010; Tahir et al., 2010a; Tahir et al., 2010b; Tariq et al., 2010) of 2,3-dimethylaniline.

The crystal structures of (II) i.e, 2,3-dimethyl-N-[(E)-4-nitrobenzylidene]aniline (Tariq et al., 2010), (III) N-[(E)-4-chlorobenzylidene]-2,3-dimethylaniline (Tahir et al., 2010a), (IV) (E)-2,3-dimethyl-N-(2-nitrobenzylidene)aniline (Tahir et al., 2010b) and (V) 2,3-dimethyl-N-[(E)-2,4,5-trimethoxybenzylidene]aniline (Hussain et al., 2010) have been published which contain 2,3-dimethylaniline moiety. The title compound differs from these due to substitutions at the benzene ring of the aldehyde moiety.

The title compound consists of two molecules in the crystallographic asymmetric unit which differ from each other geometrically. In one molecule, the group A (C1—C8) of 2,3-dimethylaniline and the group B (C9—C15) of N,N^'-dimethylbenzaldehyde are planar with r. m. s deviation of 0.009 and 0.017 Å, respectively. The N,N^'-dimethyl group C (C16/N2/C17) is of course planar. The dihedral angle between A/B, A/C and B/C is 41.08 (07)°, 38.24 (19)° and 5.17 (37)°, respectively. In second molecule, the group D (C18—C25) and group E (C26—C32) are also planar with r. m. s deviation of 0.010 and 0.018 Å, respectively. The dihedral angle between D/E is 30.44 (09)°. The N,N^'-dimethyl group F (C33/N4/C34) of this molecule makes dihedral angle of 18.40 (17)° with group D, whereas it is oriented at 12.14 (37)° with group E. In first molecule, the N-atom of 2,3-dimethylaniline is at a distance of 0.1105 (37) Å from the mean square plane of group A. In comparison to this, in second molecule, the N3 is at -0.0152 (41) Å from group D and shows that it is in plane to D. The title compound is stabilized due to weak C—H···N and C—H···π interactions (Table 1).

Related literature top

For related structures, see: Hussain et al. (2010); Tahir et al. (2010a,b); Tariq et al. (2010).

Experimental top

Equimolar quantities of 2,3-dimethylaniline and 4-(dimethylamino)benzaldehyde were refluxed in methanol for 2.5 h. The yellow solution obtained was kept at room temperature to affoard colorless prisms of (I) in 12 h.

Structure description top

For related structures, see: Hussain et al. (2010); Tahir et al. (2010a,b); Tariq et al. (2010).

Computing details top

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997) and PLATON (Spek, 2009); software used to prepare material for publication: WinGX (Farrugia, 1999) and PLATON (Spek, 2009).

Figures top

Fig. 1. View of (I) with displacement ellipsoids drawn at the 30% probability level.

N-{(E)-[4-(Dimethylamino)phenyl]methylidene}-2,3-dimethylaniline top

Crystal data top

C₁₇H₂₀N₂	Z = 4
M_r = 252.35	F(000) = 544
Triclinic, P1	D_x = 1.149 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.6556 (8) Å	Cell parameters from 2482 reflections
b = 7.7296 (8) Å	θ = 2.5–25.1°
c = 25.059 (3) Å	µ = 0.07 mm⁻¹
α = 93.843 (6)°	T = 296 K
β = 95.436 (6)°	Prism, colorless
γ = 97.431 (5)°	0.28 × 0.18 × 0.16 mm
V = 1459.1 (3) Å³

Data collection top

Bruker Kappa APEXII CCD diffractometer	5142 independent reflections
Radiation source: fine-focus sealed tube	2482 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.075
Detector resolution: 8.20 pixels mm^-1	θ_max = 25.1°, θ_min = 2.5°
ω scans	h = −9→9
Absorption correction: multi-scan (SADABS; Bruker, 2005)	k = −9→9
T_min = 0.982, T_max = 0.988	l = −29→29
20871 measured reflections

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.065	H-atom parameters constrained
wR(F²) = 0.188	w = 1/[σ²(F_o²) + (0.0834P)²] where P = (F_o² + 2F_c²)/3
S = 1.02	(Δ/σ)_max < 0.001
5142 reflections	Δρ_max = 0.49 e Å⁻³
352 parameters	Δρ_min = −0.50 e Å⁻³
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.079 (6)

Crystal data top

C₁₇H₂₀N₂	γ = 97.431 (5)°
M_r = 252.35	V = 1459.1 (3) Å³
Triclinic, P1	Z = 4
a = 7.6556 (8) Å	Mo Kα radiation
b = 7.7296 (8) Å	µ = 0.07 mm⁻¹
c = 25.059 (3) Å	T = 296 K
α = 93.843 (6)°	0.28 × 0.18 × 0.16 mm
β = 95.436 (6)°

Data collection top

Bruker Kappa APEXII CCD diffractometer	5142 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2005)	2482 reflections with I > 2σ(I)
T_min = 0.982, T_max = 0.988	R_int = 0.075
20871 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.065	0 restraints
wR(F²) = 0.188	H-atom parameters constrained
S = 1.02	Δρ_max = 0.49 e Å⁻³
5142 reflections	Δρ_min = −0.50 e Å⁻³
352 parameters

Special details top

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

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
N1	0.5198 (3)	0.0581 (3)	0.37159 (10)	0.0537 (9)
N2	0.9529 (3)	−0.1392 (4)	0.17264 (10)	0.0721 (11)
C1	0.3947 (4)	0.1128 (4)	0.40574 (12)	0.0515 (11)
C2	0.4576 (3)	0.1876 (3)	0.45733 (11)	0.0494 (11)
C3	0.3346 (4)	0.2293 (4)	0.49253 (12)	0.0543 (11)
C4	0.1557 (4)	0.1959 (4)	0.47532 (14)	0.0660 (12)
C5	0.0951 (4)	0.1219 (4)	0.42452 (14)	0.0735 (15)
C6	0.2148 (4)	0.0822 (4)	0.38967 (12)	0.0626 (12)
C7	0.6526 (4)	0.2190 (4)	0.47505 (11)	0.0648 (11)
C8	0.3963 (4)	0.3060 (4)	0.54930 (12)	0.0712 (12)
C9	0.4960 (4)	0.0717 (4)	0.32134 (12)	0.0534 (11)
C10	0.6111 (3)	0.0102 (3)	0.28366 (11)	0.0478 (10)
C11	0.7562 (4)	−0.0742 (3)	0.29931 (11)	0.0500 (10)
C12	0.8662 (3)	−0.1263 (4)	0.26331 (11)	0.0517 (11)
C13	0.8376 (4)	−0.0954 (4)	0.20859 (11)	0.0501 (11)
C14	0.6900 (4)	−0.0152 (4)	0.19267 (11)	0.0581 (11)
C15	0.5813 (4)	0.0354 (4)	0.22929 (11)	0.0551 (11)
C16	1.1113 (4)	−0.2115 (5)	0.18959 (13)	0.0881 (16)
C17	0.9234 (5)	−0.1121 (5)	0.11657 (13)	0.0966 (18)
N3	0.4573 (3)	0.3231 (3)	0.13425 (10)	0.0582 (10)
N4	0.0318 (3)	0.4923 (3)	0.33878 (10)	0.0677 (10)
C18	0.5873 (4)	0.3266 (4)	0.09694 (12)	0.0552 (11)
C19	0.5286 (4)	0.2815 (4)	0.04280 (13)	0.0580 (12)
C20	0.6535 (5)	0.2793 (4)	0.00571 (13)	0.0687 (12)
C21	0.8323 (5)	0.3209 (4)	0.02383 (15)	0.0770 (16)
C22	0.8891 (4)	0.3616 (4)	0.07720 (15)	0.0773 (16)
C23	0.7672 (4)	0.3641 (4)	0.11396 (13)	0.0685 (14)
C24	0.3328 (4)	0.2381 (5)	0.02473 (12)	0.0775 (14)
C25	0.5962 (5)	0.2378 (5)	−0.05378 (13)	0.0969 (19)
C26	0.4823 (4)	0.4361 (4)	0.17434 (12)	0.0580 (11)
C27	0.3656 (4)	0.4420 (4)	0.21654 (12)	0.0522 (11)
C28	0.2033 (4)	0.3369 (4)	0.21470 (11)	0.0539 (11)
C29	0.0937 (4)	0.3511 (4)	0.25459 (11)	0.0541 (11)
C30	0.1432 (4)	0.4714 (4)	0.29963 (11)	0.0507 (11)
C31	0.3100 (4)	0.5717 (4)	0.30267 (12)	0.0597 (12)
C32	0.4155 (4)	0.5572 (4)	0.26191 (12)	0.0581 (11)
C33	0.0955 (5)	0.5875 (5)	0.38990 (13)	0.0877 (16)
C34	−0.1493 (4)	0.4123 (5)	0.33187 (13)	0.0852 (16)
H4	0.07449	0.22425	0.49869	0.0791*
H5	−0.02589	0.09880	0.41383	0.0880*
H6	0.17451	0.03442	0.35496	0.0751*
H7A	0.67625	0.16211	0.50736	0.0974*
H7B	0.69064	0.34244	0.48182	0.0974*
H7C	0.71577	0.17235	0.44731	0.0974*
H8A	0.29609	0.33240	0.56706	0.1070*
H8B	0.47713	0.41138	0.54830	0.1070*
H8C	0.45501	0.22305	0.56858	0.1070*
H9	0.39978	0.12387	0.30800	0.0639*
H11	0.77847	−0.09560	0.33523	0.0600*
H12	0.96108	−0.18284	0.27508	0.0620*
H14	0.66535	0.00399	0.15666	0.0699*
H15	0.48395	0.08842	0.21743	0.0659*
H16A	1.17937	−0.13571	0.21817	0.1318*
H16B	1.18046	−0.22218	0.15981	0.1318*
H16C	1.07976	−0.32495	0.20210	0.1318*
H17A	0.82382	−0.19261	0.10015	0.1445*
H17B	1.02683	−0.13118	0.09935	0.1445*
H17C	0.89984	0.00571	0.11272	0.1445*
H21	0.91542	0.32108	−0.00093	0.0922*
H22	1.00947	0.38742	0.08848	0.0926*
H23	0.80506	0.39089	0.15029	0.0818*
H24A	0.29434	0.32966	0.00441	0.1161*
H24B	0.26831	0.22737	0.05565	0.1161*
H24C	0.31152	0.12950	0.00267	0.1161*
H25A	0.69802	0.25302	−0.07345	0.1451*
H25B	0.51451	0.31518	−0.06560	0.1451*
H25C	0.53964	0.11889	−0.06001	0.1451*
H26	0.58170	0.52033	0.17679	0.0697*
H28	0.16784	0.25463	0.18562	0.0645*
H29	−0.01497	0.27993	0.25174	0.0647*
H31	0.34963	0.64904	0.33269	0.0716*
H32	0.52481	0.62718	0.26472	0.0695*
H33A	0.20414	0.54926	0.40369	0.1311*
H33B	0.00866	0.56601	0.41478	0.1311*
H33C	0.11592	0.71043	0.38523	0.1311*
H34A	−0.19929	0.42302	0.29584	0.1281*
H34B	−0.21486	0.46946	0.35692	0.1281*
H34C	−0.15499	0.29064	0.33823	0.1281*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N1	0.0518 (15)	0.0591 (16)	0.0505 (16)	0.0087 (12)	0.0085 (12)	0.0006 (12)
N2	0.0697 (18)	0.102 (2)	0.0511 (17)	0.0368 (16)	0.0067 (14)	0.0055 (15)
C1	0.0469 (18)	0.0497 (18)	0.059 (2)	0.0090 (14)	0.0074 (15)	0.0060 (15)
C2	0.0499 (18)	0.0507 (19)	0.0490 (19)	0.0084 (14)	0.0072 (15)	0.0090 (14)
C3	0.057 (2)	0.0542 (19)	0.055 (2)	0.0139 (15)	0.0119 (16)	0.0076 (15)
C4	0.054 (2)	0.076 (2)	0.073 (2)	0.0180 (17)	0.0192 (17)	0.0068 (18)
C5	0.0444 (19)	0.097 (3)	0.078 (3)	0.0096 (17)	0.0077 (18)	−0.002 (2)
C6	0.052 (2)	0.077 (2)	0.057 (2)	0.0054 (16)	0.0055 (16)	−0.0008 (16)
C7	0.0543 (19)	0.076 (2)	0.063 (2)	0.0072 (16)	0.0057 (15)	0.0011 (17)
C8	0.075 (2)	0.078 (2)	0.064 (2)	0.0201 (18)	0.0142 (17)	0.0019 (18)
C9	0.0502 (18)	0.0527 (19)	0.056 (2)	0.0058 (14)	0.0031 (15)	0.0012 (15)
C10	0.0477 (17)	0.0463 (18)	0.0480 (19)	0.0037 (14)	0.0033 (14)	0.0009 (14)
C11	0.0545 (18)	0.0499 (19)	0.0425 (17)	0.0011 (14)	−0.0002 (14)	−0.0007 (14)
C12	0.0510 (18)	0.0519 (19)	0.0510 (19)	0.0107 (14)	−0.0042 (15)	0.0016 (14)
C13	0.0515 (18)	0.0473 (18)	0.0507 (19)	0.0092 (14)	0.0017 (15)	−0.0019 (14)
C14	0.066 (2)	0.066 (2)	0.0430 (18)	0.0165 (17)	−0.0015 (16)	0.0047 (15)
C15	0.0554 (19)	0.057 (2)	0.054 (2)	0.0153 (15)	0.0008 (16)	0.0046 (15)
C16	0.074 (2)	0.117 (3)	0.083 (3)	0.038 (2)	0.0180 (19)	0.016 (2)
C17	0.111 (3)	0.137 (4)	0.055 (2)	0.060 (3)	0.018 (2)	0.008 (2)
N3	0.0573 (16)	0.0650 (18)	0.0542 (17)	0.0131 (13)	0.0075 (13)	0.0073 (14)
N4	0.0573 (17)	0.0783 (19)	0.0622 (18)	−0.0033 (14)	0.0069 (14)	−0.0101 (14)
C18	0.0513 (19)	0.058 (2)	0.060 (2)	0.0128 (15)	0.0114 (16)	0.0139 (15)
C19	0.059 (2)	0.059 (2)	0.060 (2)	0.0192 (15)	0.0086 (17)	0.0093 (16)
C20	0.077 (2)	0.071 (2)	0.064 (2)	0.0244 (19)	0.0170 (19)	0.0084 (17)
C21	0.069 (2)	0.086 (3)	0.085 (3)	0.022 (2)	0.033 (2)	0.016 (2)
C22	0.056 (2)	0.093 (3)	0.084 (3)	0.0107 (19)	0.012 (2)	0.008 (2)
C23	0.054 (2)	0.085 (3)	0.068 (2)	0.0129 (17)	0.0089 (18)	0.0069 (18)
C24	0.069 (2)	0.099 (3)	0.064 (2)	0.0188 (19)	0.0003 (17)	−0.0016 (19)
C25	0.106 (3)	0.126 (4)	0.067 (3)	0.035 (3)	0.023 (2)	0.011 (2)
C26	0.0519 (19)	0.059 (2)	0.065 (2)	0.0108 (16)	0.0071 (16)	0.0120 (17)
C27	0.0496 (18)	0.0497 (19)	0.057 (2)	0.0083 (14)	0.0018 (15)	0.0041 (15)
C28	0.0551 (19)	0.053 (2)	0.0500 (19)	0.0039 (15)	−0.0014 (15)	−0.0046 (14)
C29	0.0507 (18)	0.0520 (19)	0.055 (2)	−0.0017 (14)	−0.0007 (15)	−0.0032 (15)
C30	0.0458 (18)	0.0532 (19)	0.0522 (19)	0.0054 (14)	0.0025 (14)	0.0045 (15)
C31	0.056 (2)	0.061 (2)	0.055 (2)	−0.0044 (16)	−0.0022 (16)	−0.0118 (15)
C32	0.0452 (18)	0.058 (2)	0.067 (2)	−0.0029 (14)	0.0016 (16)	−0.0005 (17)
C33	0.092 (3)	0.095 (3)	0.068 (2)	−0.006 (2)	0.016 (2)	−0.026 (2)
C34	0.069 (2)	0.090 (3)	0.092 (3)	−0.010 (2)	0.0254 (19)	−0.010 (2)

Geometric parameters (Å, º) top

N1—C1	1.428 (4)	C16—H16B	0.9600
N1—C9	1.269 (4)	C16—H16C	0.9600
N2—C13	1.376 (4)	C17—H17B	0.9600
N2—C16	1.440 (4)	C17—H17C	0.9600
N2—C17	1.436 (4)	C17—H17A	0.9600
N3—C18	1.428 (4)	C18—C19	1.395 (4)
N3—C26	1.269 (4)	C18—C23	1.390 (4)
N4—C33	1.443 (4)	C19—C20	1.396 (5)
N4—C30	1.374 (4)	C19—C24	1.512 (4)
N4—C34	1.433 (4)	C20—C21	1.390 (5)
C1—C6	1.383 (4)	C20—C25	1.514 (5)
C1—C2	1.396 (4)	C21—C22	1.369 (5)
C2—C7	1.500 (4)	C22—C23	1.373 (5)
C2—C3	1.402 (4)	C26—C27	1.450 (4)
C3—C4	1.382 (4)	C27—C28	1.389 (4)
C3—C8	1.512 (4)	C27—C32	1.388 (4)
C4—C5	1.373 (5)	C28—C29	1.372 (4)
C5—C6	1.373 (4)	C29—C30	1.403 (4)
C9—C10	1.449 (4)	C30—C31	1.398 (4)
C10—C11	1.397 (4)	C31—C32	1.368 (4)
C10—C15	1.391 (4)	C21—H21	0.9300
C11—C12	1.367 (4)	C22—H22	0.9300
C12—C13	1.409 (4)	C23—H23	0.9300
C13—C14	1.396 (4)	C24—H24A	0.9600
C14—C15	1.367 (4)	C24—H24B	0.9600
C4—H4	0.9300	C24—H24C	0.9600
C5—H5	0.9300	C25—H25A	0.9600
C6—H6	0.9300	C25—H25B	0.9600
C7—H7B	0.9600	C25—H25C	0.9600
C7—H7A	0.9600	C26—H26	0.9300
C7—H7C	0.9600	C28—H28	0.9300
C8—H8A	0.9600	C29—H29	0.9300
C8—H8B	0.9600	C31—H31	0.9300
C8—H8C	0.9600	C32—H32	0.9300
C9—H9	0.9300	C33—H33A	0.9600
C11—H11	0.9300	C33—H33B	0.9600
C12—H12	0.9300	C33—H33C	0.9600
C14—H14	0.9300	C34—H34A	0.9600
C15—H15	0.9300	C34—H34B	0.9600
C16—H16A	0.9600	C34—H34C	0.9600

C1—N1—C9	120.0 (3)	H17A—C17—H17B	109.00
C13—N2—C16	121.6 (3)	N2—C17—H17A	109.00
C13—N2—C17	121.8 (3)	N2—C17—H17B	109.00
C16—N2—C17	116.6 (3)	N2—C17—H17C	109.00
C18—N3—C26	118.4 (3)	N3—C18—C19	117.8 (3)
C30—N4—C33	121.2 (3)	N3—C18—C23	121.5 (3)
C30—N4—C34	121.6 (3)	C19—C18—C23	120.7 (3)
C33—N4—C34	117.2 (3)	C18—C19—C20	118.9 (3)
C2—C1—C6	120.5 (3)	C18—C19—C24	120.3 (3)
N1—C1—C6	121.1 (3)	C20—C19—C24	120.8 (3)
N1—C1—C2	118.3 (3)	C19—C20—C21	119.1 (3)
C1—C2—C3	118.6 (2)	C19—C20—C25	120.9 (3)
C3—C2—C7	120.8 (2)	C21—C20—C25	120.0 (3)
C1—C2—C7	120.6 (2)	C20—C21—C22	121.7 (3)
C2—C3—C8	120.5 (3)	C21—C22—C23	119.6 (3)
C4—C3—C8	120.1 (3)	C18—C23—C22	120.1 (3)
C2—C3—C4	119.4 (3)	N3—C26—C27	124.1 (3)
C3—C4—C5	121.5 (3)	C26—C27—C28	123.7 (3)
C4—C5—C6	119.4 (3)	C26—C27—C32	119.6 (3)
C1—C6—C5	120.6 (3)	C28—C27—C32	116.7 (3)
N1—C9—C10	123.4 (3)	C27—C28—C29	121.8 (3)
C9—C10—C15	120.4 (2)	C28—C29—C30	121.0 (3)
C11—C10—C15	116.8 (2)	N4—C30—C29	121.6 (3)
C9—C10—C11	122.9 (3)	N4—C30—C31	121.2 (3)
C10—C11—C12	121.9 (3)	C29—C30—C31	117.2 (3)
C11—C12—C13	120.8 (3)	C30—C31—C32	120.7 (3)
C12—C13—C14	117.3 (3)	C27—C32—C31	122.5 (3)
N2—C13—C12	121.2 (3)	C20—C21—H21	119.00
N2—C13—C14	121.5 (3)	C22—C21—H21	119.00
C13—C14—C15	120.9 (3)	C21—C22—H22	120.00
C10—C15—C14	122.3 (3)	C23—C22—H22	120.00
C3—C4—H4	119.00	C18—C23—H23	120.00
C5—C4—H4	119.00	C22—C23—H23	120.00
C4—C5—H5	120.00	C19—C24—H24A	109.00
C6—C5—H5	120.00	C19—C24—H24B	109.00
C1—C6—H6	120.00	C19—C24—H24C	109.00
C5—C6—H6	120.00	H24A—C24—H24B	110.00
C2—C7—H7B	110.00	H24A—C24—H24C	109.00
C2—C7—H7C	109.00	H24B—C24—H24C	109.00
C2—C7—H7A	109.00	C20—C25—H25A	109.00
H7B—C7—H7C	109.00	C20—C25—H25B	109.00
H7A—C7—H7B	109.00	C20—C25—H25C	109.00
H7A—C7—H7C	109.00	H25A—C25—H25B	109.00
C3—C8—H8C	109.00	H25A—C25—H25C	109.00
H8B—C8—H8C	109.00	H25B—C25—H25C	109.00
H8A—C8—H8B	109.00	N3—C26—H26	118.00
H8A—C8—H8C	109.00	C27—C26—H26	118.00
C3—C8—H8B	109.00	C27—C28—H28	119.00
C3—C8—H8A	110.00	C29—C28—H28	119.00
N1—C9—H9	118.00	C28—C29—H29	120.00
C10—C9—H9	118.00	C30—C29—H29	120.00
C10—C11—H11	119.00	C30—C31—H31	120.00
C12—C11—H11	119.00	C32—C31—H31	120.00
C13—C12—H12	120.00	C27—C32—H32	119.00
C11—C12—H12	120.00	C31—C32—H32	119.00
C13—C14—H14	120.00	N4—C33—H33A	109.00
C15—C14—H14	120.00	N4—C33—H33B	109.00
C14—C15—H15	119.00	N4—C33—H33C	109.00
C10—C15—H15	119.00	H33A—C33—H33B	109.00
N2—C16—H16B	109.00	H33A—C33—H33C	110.00
N2—C16—H16C	109.00	H33B—C33—H33C	109.00
H16A—C16—H16B	109.00	N4—C34—H34A	109.00
H16A—C16—H16C	109.00	N4—C34—H34B	109.00
N2—C16—H16A	110.00	N4—C34—H34C	109.00
H16B—C16—H16C	109.00	H34A—C34—H34B	110.00
H17A—C17—H17C	109.00	H34A—C34—H34C	109.00
H17B—C17—H17C	109.00	H34B—C34—H34C	109.00

C9—N1—C1—C2	−145.2 (3)	C9—C10—C11—C12	−177.9 (3)
C9—N1—C1—C6	39.0 (4)	C10—C11—C12—C13	0.4 (4)
C1—N1—C9—C10	−176.4 (3)	C11—C12—C13—N2	176.6 (3)
C16—N2—C13—C14	175.9 (3)	C11—C12—C13—C14	−2.0 (4)
C16—N2—C13—C12	−2.6 (5)	N2—C13—C14—C15	−176.8 (3)
C17—N2—C13—C12	178.6 (3)	C12—C13—C14—C15	1.8 (5)
C17—N2—C13—C14	−2.9 (5)	C13—C14—C15—C10	0.0 (5)
C26—N3—C18—C23	38.3 (4)	N3—C18—C19—C24	2.5 (4)
C18—N3—C26—C27	−176.9 (3)	C23—C18—C19—C20	−1.7 (5)
C26—N3—C18—C19	−145.2 (3)	N3—C18—C19—C20	−178.3 (3)
C34—N4—C30—C31	169.5 (3)	N3—C18—C23—C22	178.2 (3)
C33—N4—C30—C31	−14.2 (4)	C19—C18—C23—C22	1.8 (5)
C33—N4—C30—C29	166.9 (3)	C23—C18—C19—C24	179.0 (3)
C34—N4—C30—C29	−9.5 (4)	C24—C19—C20—C21	179.7 (3)
C2—C1—C6—C5	−1.2 (5)	C18—C19—C20—C21	0.4 (5)
C6—C1—C2—C7	179.3 (3)	C18—C19—C20—C25	−177.7 (3)
N1—C1—C6—C5	174.4 (3)	C24—C19—C20—C25	1.5 (5)
N1—C1—C2—C3	−175.2 (3)	C25—C20—C21—C22	179.1 (3)
C6—C1—C2—C3	0.6 (4)	C19—C20—C21—C22	0.9 (5)
N1—C1—C2—C7	3.5 (4)	C20—C21—C22—C23	−0.9 (5)
C7—C2—C3—C4	−178.8 (3)	C21—C22—C23—C18	−0.4 (5)
C7—C2—C3—C8	−0.4 (4)	N3—C26—C27—C28	−7.5 (5)
C1—C2—C3—C4	−0.2 (4)	N3—C26—C27—C32	172.2 (3)
C1—C2—C3—C8	178.3 (3)	C26—C27—C28—C29	−177.5 (3)
C8—C3—C4—C5	−178.2 (3)	C32—C27—C28—C29	2.8 (5)
C2—C3—C4—C5	0.3 (5)	C26—C27—C32—C31	178.7 (3)
C3—C4—C5—C6	−0.9 (5)	C28—C27—C32—C31	−1.6 (5)
C4—C5—C6—C1	1.3 (5)	C27—C28—C29—C30	−1.1 (5)
N1—C9—C10—C11	1.8 (4)	C28—C29—C30—N4	177.2 (3)
N1—C9—C10—C15	−177.5 (3)	C28—C29—C30—C31	−1.7 (4)
C9—C10—C15—C14	177.8 (3)	N4—C30—C31—C32	−176.1 (3)
C11—C10—C15—C14	−1.6 (4)	C29—C30—C31—C32	2.9 (4)
C15—C10—C11—C12	1.4 (4)	C30—C31—C32—C27	−1.2 (5)

Hydrogen-bond geometry (Å, º) top

Cg1, Cg2 and Cg4 are the centroids of the C1–C6, C10–C15 and C27–C32 benzene rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
C7—H7A···Cg1ⁱ	0.96	2.90	3.756 (3)	149
C16—H16C···Cg4ⁱⁱ	0.96	2.69	3.434 (4)	135
C32—H32···Cg2ⁱⁱⁱ	0.93	2.88	3.698 (3)	148

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

Experimental details

Crystal data
Chemical formula	C₁₇H₂₀N₂
M_r	252.35
Crystal system, space group	Triclinic, P1
Temperature (K)	296
a, b, c (Å)	7.6556 (8), 7.7296 (8), 25.059 (3)
α, β, γ (°)	93.843 (6), 95.436 (6), 97.431 (5)
V (Å³)	1459.1 (3)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.07
Crystal size (mm)	0.28 × 0.18 × 0.16

Data collection
Diffractometer	Bruker Kappa APEXII CCD
Absorption correction	Multi-scan (SADABS; Bruker, 2005)
T_min, T_max	0.982, 0.988
No. of measured, independent and observed [I > 2σ(I)] reflections	20871, 5142, 2482
R_int	0.075
(sin θ/λ)_max (Å⁻¹)	0.596

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.065, 0.188, 1.02
No. of reflections	5142
No. of parameters	352
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.49, −0.50

Computer programs: APEX2 (Bruker, 2009), SAINT (Bruker, 2009), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997) and PLATON (Spek, 2009), WinGX (Farrugia, 1999) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

Cg1, Cg2 and Cg4 are the centroids of the C1–C6, C10–C15 and C27–C32 benzene rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
C7—H7A···Cg1ⁱ	0.96	2.90	3.756 (3)	149
C16—H16C···Cg4ⁱⁱ	0.96	2.69	3.434 (4)	135
C32—H32···Cg2ⁱⁱⁱ	0.93	2.88	3.698 (3)	148

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

Acknowledgements

The authors acknowledge the provision of funds for the purchase of diffractometer and encouragement by Dr Muhammad Akram Chaudhary, Vice Chancellor, University of Sargodha, Pakistan.

References

Bruker (2005). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Bruker (2009). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. CrossRef IUCr Journals Google Scholar
Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837–838. CrossRef CAS IUCr Journals Google Scholar
Hussain, A., Tahir, M. N., Tariq, M. I., Ahmad, S. & Asiri, A. M. (2010). Acta Cryst. E66, o1953. Web of Science CSD CrossRef IUCr Journals 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
Tahir, M. N., Tariq, M. I., Ahmad, S., Sarfraz, M. & Ather, A. Q. (2010a). Acta Cryst. E66, o1562. Web of Science CSD CrossRef IUCr Journals Google Scholar
Tahir, M. N., Tariq, M. I., Ahmad, S., Sarfraz, M. & Ather, A. Q. (2010b). Acta Cryst. E66, o1817. Web of Science CSD CrossRef IUCr Journals Google Scholar
Tariq, M. I., Ahmad, S., Tahir, M. N., Sarfaraz, M. & Hussain, I. (2010). Acta Cryst. E66, o1561. Web of Science CSD CrossRef IUCr Journals Google Scholar

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