N-{4-[(E)-(4-Methyl­phen­yl)imino­meth­yl]phen­yl}acetamide

Tahir, M.N.; Shad, H.A.

doi:10.1107/S1600536811001887

organic compounds

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ISSN: 2056-9890

Volume 67| Part 2| February 2011| Page o443

doi:10.1107/S1600536811001887

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N-{4-[(E)-(4-Methylphenyl)iminomethyl]phenyl}acetamide

M. Nawaz Tahir ^a ^* and Hazoor Ahmad Shad ^b

^aDepartment of Physics, University of Sargodha, Sargodha, Pakistan, and ^bDepartment of Chemistry, Govt. M. D. College, Toba Tek Singh, Punjab, Pakistan
^*Correspondence e-mail: dmntahir_uos@yahoo.com

(Received 12 January 2011; accepted 12 January 2011; online 22 January 2011)

There are two symmetry-independent molecules in the asymmetric unit of the title compound, C₁₆H₁₆N₂O, that differ in conformation. The dihedral angles between the benzene rings in the two molecules are 44.35 (19) and 48.14 (17)°, but the rings twist in opposite directions. The acetamide groups make nearly equal dihedral angles of 25.4 (3) and 25.7 (3)° with the parent benzene rings. An S(6) ring motif is formed in each molecule by intramolecular C—H⋯O close contacts. In the crystal, strong N—H⋯O hydrogen bonds between acetamide groups generate a C(4) chain motif arranging the molecules into two symmetry-independent polymeric structures extending along [010].

Related literature

For related structures, see: Karlsen et al. (1988 ); Tahir et al. (2010 ). For graph-set notation, see: Bernstein et al. (1995 ).

Experimental

Crystal data

C₁₆H₁₆N₂O
M_r = 252.31
Triclinic, P 1
a = 7.1044 (8) Å
b = 9.7393 (10) Å
c = 10.9236 (12) Å
α = 109.731 (5)°
β = 91.799 (6)°
γ = 100.679 (6)°
V = 695.51 (13) Å³
Z = 2
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 296 K
0.26 × 0.16 × 0.12 mm

Data collection

Bruker Kappa APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2005 ) T_min = 0.980, T_max = 0.990
10024 measured reflections
2453 independent reflections
1460 reflections with I > 2σ(I)
R_int = 0.059

Refinement

R[F² > 2σ(F²)] = 0.044
wR(F²) = 0.112
S = 0.97
2453 reflections
339 parameters
3 restraints
H-atom parameters constrained
Δρ_max = 0.16 e Å⁻³
Δρ_min = −0.15 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2A⋯O2ⁱ	0.86	2.00	2.854 (5)	172
N4—H4⋯O1ⁱⁱ	0.86	2.06	2.911 (4)	173
C13—H13⋯O1	0.93	2.40	2.922 (6)	116
C29—H29⋯O2	0.93	2.35	2.864 (6)	114
Symmetry codes: (i) x+2, y, z-1; (ii) x-2, y-1, z+1.

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 for Windows (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: 10.1107/S1600536811001887/gk2340sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811001887/gk2340Isup2.hkl

checkCIF report

Comment top

The title compound (I, Fig. 1) is being reported as a part of our ongoing project related to the synthesis of various Schiff bases of 4-methylaniline. In this regard recently we have reported the synthesis and crystal structure of N-[(E)-1,3-benzodioxol-5-ylmethylidene]-4-methylaniline (Tahir et al., 2010).

The crystal structure of thiacetazone i.e., N-{4-[-(2-carbamothioylhydrazinylidene)methyl]phenyl}acetamide (Karlsen et al., 1988) has been published which contains the common moiety of N-(4-formylphenyl)acetamide as in (I).

The title compound consists of two molecules in the crystallographic asymmetric unit which differ from each other geometrically. In one molecule, the 4-methylaniline group A (C1—C7/N1), groups B (C8—C14) and C (N2/C15/C16/O1) of N-(4-formylphenyl)acetamide are planar with r. m. s deviation of 0.0062, 0.0169 and 0.0005 Å, respectively. The dihedral angle between A/B, A/C and B/C is 48.11 (15)°, 25.13 (25)° and 25.88 (27)°, respectively. In second molecule, the 4-methylaniline group D (C17—C23/N3), groups E (C24—C30) and F (N4/C31/C32/O2) of N-(4-formylphenyl)acetamide are planar with r. m. s deviation of 0.0292, 0.0146 and 0.0027 Å, respectively. The dihedral angle between D/E, D/F and E/F is 44.36 (17)°, 69.79 (17)° and 25.43 (23)°, respectively. In each molecule there exist S(6) ring motif (Bernstein et al., 1995) due to intramolecular H-bonding of C—H···O type (Table 1, Fig. 1). The molecules are stabilized in the form of one dimensional polymeric chains extending along the crystallographic b-axis due to intermolecular hydrogen bonds of N—H···O type (Table 1, Fig. 2). These C(4) chains (Bernstein et al., 1995) are formed via interaction of the amide groups. There does not exist any kind of strong π-interaction.

Related literature top

For related structures, see: Karlsen et al. (1988); Tahir et al. (2010). For graph-set notation, see: Bernstein et al. (1995).

Experimental top

Equimolar quantities of 4-methylaniline and N-(4-formylphenyl)acetamide were refluxed in methanol along with a few drops of acetic acid as catalyst for 30 min resulting in colorless solution. The solution was kept at room temperature. After six days colourless needles of the title compound were isolated.

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 for Windows (Farrugia, 1997) and PLATON (Spek, 2009); software used to prepare material for publication: WinGX (Farrugia, 1999) and PLATON (Spek, 2009).

Figures top

	Fig. 1. Molecular structure of the title compound with the atom numbering scheme. The displacement ellipsoids are drawn at the 50% probability level. H atoms are shown by small circles of arbitrary radii. The dotted line represent the intramolecular hydrogen bond.
	Fig. 2. The crystal packing (PLATON; Spek, 2009) showing two symmetry independent one dimensional polymeric chains along the b-axis.

N-{4-[(E)-(4-Methylphenyl)iminomethyl]phenyl}acetamide top

Crystal data top

C₁₆H₁₆N₂O	Z = 2
M_r = 252.31	F(000) = 268
Triclinic, P1	D_x = 1.205 Mg m⁻³
Hall symbol: P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.1044 (8) Å	Cell parameters from 1460 reflections
b = 9.7393 (10) Å	θ = 2.0–25.1°
c = 10.9236 (12) Å	µ = 0.08 mm⁻¹
α = 109.731 (5)°	T = 296 K
β = 91.799 (6)°	Needle, colorless
γ = 100.679 (6)°	0.26 × 0.16 × 0.12 mm
V = 695.51 (13) Å³

Data collection top

Bruker Kappa APEXII CCD diffractometer	2453 independent reflections
Radiation source: fine-focus sealed tube	1460 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.059
Detector resolution: 8.20 pixels mm^-1	θ_max = 25.1°, θ_min = 2.0°
ω scans	h = −8→8
Absorption correction: multi-scan (SADABS; Bruker, 2005)	k = −10→11
T_min = 0.980, T_max = 0.990	l = −13→13
10024 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)] = 0.044	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.112	H-atom parameters constrained
S = 0.97	w = 1/[σ²(F_o²) + (0.052P)²] where P = (F_o² + 2F_c²)/3
2453 reflections	(Δ/σ)_max < 0.001
339 parameters	Δρ_max = 0.16 e Å⁻³
3 restraints	Δρ_min = −0.15 e Å⁻³

Crystal data top

C₁₆H₁₆N₂O	γ = 100.679 (6)°
M_r = 252.31	V = 695.51 (13) Å³
Triclinic, P1	Z = 2
a = 7.1044 (8) Å	Mo Kα radiation
b = 9.7393 (10) Å	µ = 0.08 mm⁻¹
c = 10.9236 (12) Å	T = 296 K
α = 109.731 (5)°	0.26 × 0.16 × 0.12 mm
β = 91.799 (6)°

Data collection top

Bruker Kappa APEXII CCD diffractometer	2453 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2005)	1460 reflections with I > 2σ(I)
T_min = 0.980, T_max = 0.990	R_int = 0.059
10024 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.044	3 restraints
wR(F²) = 0.112	H-atom parameters constrained
S = 0.97	Δρ_max = 0.16 e Å⁻³
2453 reflections	Δρ_min = −0.15 e Å⁻³
339 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
O1	1.4696 (5)	1.0625 (3)	−0.3349 (3)	0.0708 (16)
N1	0.7543 (5)	0.8296 (4)	0.1036 (4)	0.0574 (17)
N2	1.4290 (5)	0.8628 (4)	−0.2684 (4)	0.0507 (14)
C1	0.5901 (7)	0.8407 (5)	0.1748 (5)	0.0533 (17)
C2	0.4818 (7)	0.7111 (5)	0.1826 (5)	0.0581 (19)
C3	0.3211 (7)	0.7168 (5)	0.2509 (5)	0.0609 (19)
C4	0.2630 (7)	0.8479 (5)	0.3122 (5)	0.057 (2)
C5	0.3734 (7)	0.9758 (5)	0.3047 (5)	0.066 (2)
C6	0.5329 (7)	0.9738 (5)	0.2353 (5)	0.063 (2)
C7	0.0872 (8)	0.8530 (7)	0.3878 (6)	0.082 (3)
C8	0.7950 (7)	0.9097 (5)	0.0340 (5)	0.0546 (17)
C9	0.9643 (7)	0.9052 (5)	−0.0396 (4)	0.0488 (17)
C10	1.1009 (7)	0.8263 (5)	−0.0238 (5)	0.0560 (17)
C11	1.2543 (7)	0.8186 (5)	−0.0978 (4)	0.0527 (17)
C12	1.2758 (6)	0.8876 (5)	−0.1894 (4)	0.0461 (17)
C13	1.1414 (6)	0.9688 (5)	−0.2060 (4)	0.0525 (17)
C14	0.9869 (7)	0.9764 (5)	−0.1296 (5)	0.0568 (17)
C15	1.5113 (6)	0.9450 (5)	−0.3384 (4)	0.0530 (17)
C16	1.6605 (5)	0.8800 (3)	−0.4230 (4)	0.0656 (19)
O2	−0.4539 (3)	0.5959 (2)	0.7256 (3)	0.0861 (18)
N3	0.2922 (3)	0.3139 (2)	0.2969 (3)	0.0618 (17)
N4	−0.3891 (3)	0.3652 (2)	0.6710 (3)	0.0590 (17)
C17	0.4543 (7)	0.3342 (5)	0.2265 (5)	0.055 (2)
C18	0.4305 (7)	0.2583 (5)	0.0940 (5)	0.0638 (19)
C19	0.5805 (8)	0.2744 (5)	0.0169 (5)	0.0649 (19)
C20	0.7579 (8)	0.3651 (6)	0.0740 (6)	0.061 (2)
C21	0.7813 (7)	0.4324 (6)	0.2065 (6)	0.073 (2)
C22	0.6329 (7)	0.4202 (5)	0.2829 (5)	0.0637 (17)
C23	0.9201 (8)	0.3872 (7)	−0.0095 (7)	0.093 (3)
C24	0.2638 (7)	0.4188 (5)	0.3945 (5)	0.060 (2)
C25	0.0999 (7)	0.4058 (5)	0.4693 (5)	0.0534 (17)
C26	−0.0233 (8)	0.2677 (5)	0.4452 (5)	0.067 (2)
C27	−0.1822 (8)	0.2570 (5)	0.5138 (5)	0.063 (2)
C28	−0.2240 (7)	0.3849 (5)	0.6071 (5)	0.0509 (19)
C29	−0.1015 (7)	0.5213 (5)	0.6306 (5)	0.0594 (19)
C30	0.0582 (7)	0.5293 (5)	0.5624 (5)	0.0601 (19)
C31	−0.4956 (7)	0.4670 (5)	0.7260 (5)	0.0609 (19)
C32	−0.6685 (8)	0.4123 (6)	0.7853 (6)	0.082 (3)
H2	0.51695	0.62027	0.14207	0.0694*
H2A	1.47558	0.78614	−0.27236	0.0609*
H3	0.24979	0.62868	0.25548	0.0730*
H5	0.33978	1.06663	0.34770	0.0789*
H6	0.60181	1.06190	0.22925	0.0763*
H7A	−0.01968	0.85851	0.33489	0.1221*
H7B	0.11396	0.93911	0.46638	0.1221*
H7C	0.05609	0.76452	0.40979	0.1221*
H8	0.71485	0.97357	0.02934	0.0652*
H10	1.08883	0.77836	0.03701	0.0673*
H11	1.34542	0.76574	−0.08575	0.0631*
H13	1.15408	1.01698	−0.26662	0.0630*
H14	0.89694	1.03103	−0.13976	0.0682*
H16A	1.61524	0.85273	−0.51349	0.0982*
H16B	1.68204	0.79327	−0.40626	0.0982*
H16C	1.77890	0.95295	−0.40297	0.0982*
H4	−0.42705	0.27822	0.67571	0.0708*
H18	0.31304	0.19551	0.05503	0.0760*
H19	0.56128	0.22404	−0.07300	0.0775*
H21	0.90168	0.48860	0.24676	0.0868*
H22	0.65334	0.47021	0.37281	0.0761*
H23A	0.95401	0.49052	−0.00053	0.1393*
H23B	0.87856	0.32785	−0.09943	0.1393*
H23C	1.03017	0.35732	0.01878	0.1393*
H24	0.35200	0.50929	0.42033	0.0709*
H26	0.00187	0.18264	0.38272	0.0806*
H27	−0.26223	0.16437	0.49809	0.0755*
H29	−0.12660	0.60711	0.69199	0.0708*
H30	0.14046	0.62137	0.57995	0.0723*
H32A	−0.75807	0.47678	0.79349	0.1221*
H32B	−0.62896	0.41233	0.87019	0.1221*
H32C	−0.72896	0.31278	0.73023	0.1221*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.085 (3)	0.051 (2)	0.086 (3)	0.0129 (18)	0.032 (2)	0.0348 (19)
N1	0.051 (3)	0.062 (3)	0.063 (3)	0.010 (2)	0.015 (2)	0.027 (2)
N2	0.052 (2)	0.044 (2)	0.061 (3)	0.0141 (18)	0.013 (2)	0.022 (2)
C1	0.051 (3)	0.060 (3)	0.057 (3)	0.016 (2)	0.012 (3)	0.028 (3)
C2	0.060 (3)	0.058 (3)	0.064 (4)	0.016 (2)	0.010 (3)	0.029 (3)
C3	0.061 (3)	0.058 (3)	0.075 (4)	0.011 (2)	0.013 (3)	0.038 (3)
C4	0.051 (3)	0.071 (4)	0.057 (4)	0.018 (3)	0.007 (3)	0.030 (3)
C5	0.071 (4)	0.058 (3)	0.072 (4)	0.020 (3)	0.019 (3)	0.022 (3)
C6	0.066 (4)	0.052 (3)	0.073 (4)	0.006 (3)	0.021 (3)	0.025 (3)
C7	0.071 (4)	0.104 (5)	0.083 (4)	0.023 (3)	0.024 (4)	0.046 (4)
C8	0.051 (3)	0.057 (3)	0.056 (3)	0.011 (2)	0.008 (3)	0.020 (3)
C9	0.047 (3)	0.051 (3)	0.051 (3)	0.010 (2)	0.008 (3)	0.021 (2)
C10	0.064 (3)	0.058 (3)	0.053 (3)	0.014 (3)	0.014 (3)	0.027 (3)
C11	0.057 (3)	0.055 (3)	0.052 (3)	0.014 (2)	0.005 (3)	0.025 (3)
C12	0.044 (3)	0.049 (3)	0.046 (3)	0.008 (2)	0.008 (3)	0.018 (2)
C13	0.053 (3)	0.052 (3)	0.057 (3)	0.010 (2)	0.008 (3)	0.025 (2)
C14	0.053 (3)	0.062 (3)	0.062 (3)	0.014 (2)	0.006 (3)	0.029 (3)
C15	0.055 (3)	0.047 (3)	0.050 (3)	0.001 (2)	0.006 (3)	0.013 (2)
C16	0.061 (3)	0.069 (3)	0.073 (4)	0.014 (3)	0.024 (3)	0.031 (3)
O2	0.081 (3)	0.060 (2)	0.133 (4)	0.0285 (18)	0.030 (2)	0.045 (2)
N3	0.066 (3)	0.056 (3)	0.064 (3)	0.011 (2)	0.014 (3)	0.022 (2)
N4	0.064 (3)	0.050 (3)	0.075 (3)	0.021 (2)	0.023 (3)	0.031 (2)
C17	0.061 (4)	0.045 (3)	0.060 (4)	0.010 (2)	0.011 (3)	0.020 (3)
C18	0.061 (3)	0.056 (3)	0.065 (4)	0.007 (2)	0.006 (3)	0.012 (3)
C19	0.075 (4)	0.060 (3)	0.054 (3)	0.015 (3)	0.009 (3)	0.012 (3)
C20	0.063 (4)	0.063 (3)	0.064 (4)	0.015 (3)	0.015 (3)	0.028 (3)
C21	0.050 (3)	0.080 (4)	0.082 (5)	0.005 (3)	0.005 (3)	0.025 (3)
C22	0.061 (3)	0.071 (3)	0.057 (3)	0.011 (3)	−0.002 (3)	0.022 (3)
C23	0.071 (4)	0.098 (4)	0.104 (5)	0.014 (3)	0.031 (4)	0.029 (4)
C24	0.068 (4)	0.046 (3)	0.059 (4)	0.000 (2)	0.003 (3)	0.018 (3)
C25	0.053 (3)	0.052 (3)	0.057 (3)	0.006 (2)	0.006 (3)	0.024 (3)
C26	0.084 (4)	0.047 (3)	0.070 (4)	0.015 (3)	0.026 (4)	0.018 (3)
C27	0.079 (4)	0.040 (3)	0.072 (4)	0.008 (3)	0.021 (3)	0.023 (3)
C28	0.055 (3)	0.043 (3)	0.057 (4)	0.007 (2)	0.006 (3)	0.022 (3)
C29	0.065 (3)	0.050 (3)	0.063 (4)	0.013 (2)	0.006 (3)	0.019 (3)
C30	0.063 (3)	0.047 (3)	0.066 (4)	0.004 (2)	0.009 (3)	0.018 (3)
C31	0.062 (3)	0.060 (3)	0.070 (4)	0.019 (3)	0.009 (3)	0.031 (3)
C32	0.078 (4)	0.090 (4)	0.104 (5)	0.034 (3)	0.034 (4)	0.058 (4)

Geometric parameters (Å, º) top

O1—C15	1.223 (6)	C11—H11	0.9300
O2—C31	1.237 (6)	C13—H13	0.9300
N1—C1	1.423 (6)	C14—H14	0.9300
N1—C8	1.265 (7)	C16—H16C	0.9600
N2—C12	1.415 (6)	C16—H16A	0.9600
N2—C15	1.355 (6)	C16—H16B	0.9600
N2—H2A	0.8600	C17—C22	1.378 (7)
N3—C24	1.255 (6)	C17—C18	1.373 (7)
N3—C17	1.425 (6)	C18—C19	1.398 (7)
N4—C28	1.399 (6)	C19—C20	1.387 (8)
N4—C31	1.349 (6)	C20—C21	1.362 (9)
N4—H4	0.8600	C20—C23	1.521 (9)
C1—C2	1.382 (7)	C21—C22	1.378 (8)
C1—C6	1.384 (7)	C24—C25	1.454 (7)
C2—C3	1.383 (7)	C25—C30	1.376 (7)
C3—C4	1.373 (7)	C25—C26	1.398 (7)
C4—C5	1.373 (7)	C26—C27	1.382 (8)
C4—C7	1.518 (8)	C27—C28	1.406 (7)
C5—C6	1.383 (7)	C28—C29	1.384 (7)
C8—C9	1.467 (7)	C29—C30	1.381 (7)
C9—C10	1.385 (7)	C31—C32	1.501 (8)
C9—C14	1.379 (7)	C18—H18	0.9300
C10—C11	1.375 (7)	C19—H19	0.9300
C11—C12	1.379 (7)	C21—H21	0.9300
C12—C13	1.391 (7)	C22—H22	0.9300
C13—C14	1.397 (7)	C23—H23A	0.9600
C15—C16	1.514 (6)	C23—H23B	0.9600
C2—H2	0.9300	C23—H23C	0.9600
C3—H3	0.9300	C24—H24	0.9300
C5—H5	0.9300	C26—H26	0.9300
C6—H6	0.9300	C27—H27	0.9300
C7—H7C	0.9600	C29—H29	0.9300
C7—H7A	0.9600	C30—H30	0.9300
C7—H7B	0.9600	C32—H32A	0.9600
C8—H8	0.9300	C32—H32B	0.9600
C10—H10	0.9300	C32—H32C	0.9600

C1—N1—C8	119.8 (4)	H16A—C16—H16B	109.00
C12—N2—C15	128.0 (4)	C15—C16—H16A	109.00
C15—N2—H2A	116.00	C15—C16—H16C	109.00
C12—N2—H2A	116.00	C15—C16—H16B	110.00
C17—N3—C24	120.6 (4)	N3—C17—C22	124.5 (4)
C28—N4—C31	127.5 (3)	N3—C17—C18	117.0 (4)
C31—N4—H4	116.00	C18—C17—C22	118.4 (5)
C28—N4—H4	116.00	C17—C18—C19	120.9 (5)
N1—C1—C6	123.5 (5)	C18—C19—C20	120.2 (5)
N1—C1—C2	117.9 (4)	C19—C20—C21	117.8 (5)
C2—C1—C6	118.6 (5)	C19—C20—C23	120.6 (5)
C1—C2—C3	119.8 (5)	C21—C20—C23	121.6 (5)
C2—C3—C4	122.4 (5)	C20—C21—C22	122.3 (5)
C3—C4—C7	121.9 (5)	C17—C22—C21	120.2 (5)
C5—C4—C7	121.0 (5)	N3—C24—C25	123.2 (4)
C3—C4—C5	117.1 (5)	C24—C25—C30	121.1 (5)
C4—C5—C6	122.1 (5)	C26—C25—C30	118.3 (5)
C1—C6—C5	120.0 (5)	C24—C25—C26	120.6 (5)
N1—C8—C9	122.2 (5)	C25—C26—C27	120.3 (5)
C10—C9—C14	118.6 (5)	C26—C27—C28	120.6 (5)
C8—C9—C10	121.2 (4)	N4—C28—C27	117.1 (4)
C8—C9—C14	120.1 (5)	C27—C28—C29	118.9 (5)
C9—C10—C11	120.2 (5)	N4—C28—C29	124.0 (4)
C10—C11—C12	121.4 (5)	C28—C29—C30	119.7 (5)
N2—C12—C11	117.2 (4)	C25—C30—C29	122.3 (5)
C11—C12—C13	119.4 (4)	N4—C31—C32	115.5 (4)
N2—C12—C13	123.3 (4)	O2—C31—N4	121.9 (4)
C12—C13—C14	118.6 (4)	O2—C31—C32	122.7 (5)
C9—C14—C13	121.8 (5)	C17—C18—H18	120.00
N2—C15—C16	114.8 (4)	C19—C18—H18	120.00
O1—C15—C16	121.9 (4)	C18—C19—H19	120.00
O1—C15—N2	123.4 (4)	C20—C19—H19	120.00
C1—C2—H2	120.00	C20—C21—H21	119.00
C3—C2—H2	120.00	C22—C21—H21	119.00
C2—C3—H3	119.00	C17—C22—H22	120.00
C4—C3—H3	119.00	C21—C22—H22	120.00
C6—C5—H5	119.00	C20—C23—H23A	109.00
C4—C5—H5	119.00	C20—C23—H23B	109.00
C1—C6—H6	120.00	C20—C23—H23C	109.00
C5—C6—H6	120.00	H23A—C23—H23B	109.00
H7A—C7—H7C	109.00	H23A—C23—H23C	109.00
H7B—C7—H7C	110.00	H23B—C23—H23C	109.00
C4—C7—H7A	109.00	N3—C24—H24	118.00
C4—C7—H7B	109.00	C25—C24—H24	118.00
C4—C7—H7C	109.00	C25—C26—H26	120.00
H7A—C7—H7B	109.00	C27—C26—H26	120.00
N1—C8—H8	119.00	C26—C27—H27	120.00
C9—C8—H8	119.00	C28—C27—H27	120.00
C11—C10—H10	120.00	C28—C29—H29	120.00
C9—C10—H10	120.00	C30—C29—H29	120.00
C10—C11—H11	119.00	C25—C30—H30	119.00
C12—C11—H11	119.00	C29—C30—H30	119.00
C14—C13—H13	121.00	C31—C32—H32A	109.00
C12—C13—H13	121.00	C31—C32—H32B	109.00
C9—C14—H14	119.00	C31—C32—H32C	109.00
C13—C14—H14	119.00	H32A—C32—H32B	109.00
H16A—C16—H16C	109.00	H32A—C32—H32C	109.00
H16B—C16—H16C	109.00	H32B—C32—H32C	109.00

C8—N1—C1—C2	141.7 (5)	C10—C9—C14—C13	1.0 (7)
C8—N1—C1—C6	−37.7 (7)	C9—C10—C11—C12	−0.4 (7)
C1—N1—C8—C9	178.8 (4)	C10—C11—C12—N2	−174.8 (4)
C15—N2—C12—C11	−160.9 (4)	C10—C11—C12—C13	1.1 (7)
C15—N2—C12—C13	23.5 (7)	N2—C12—C13—C14	174.9 (4)
C12—N2—C15—O1	5.3 (7)	C11—C12—C13—C14	−0.7 (7)
C12—N2—C15—C16	−174.5 (4)	C12—C13—C14—C9	−0.4 (7)
C24—N3—C17—C18	−146.3 (5)	N3—C17—C18—C19	178.5 (4)
C24—N3—C17—C22	35.9 (7)	C22—C17—C18—C19	−3.6 (8)
C17—N3—C24—C25	179.1 (4)	N3—C17—C22—C21	179.7 (5)
C31—N4—C28—C27	−154.6 (5)	C18—C17—C22—C21	1.9 (8)
C31—N4—C28—C29	25.5 (7)	C17—C18—C19—C20	1.5 (8)
C28—N4—C31—O2	−0.4 (7)	C18—C19—C20—C21	2.2 (8)
C28—N4—C31—C32	178.7 (4)	C18—C19—C20—C23	−178.1 (5)
N1—C1—C2—C3	180.0 (5)	C19—C20—C21—C22	−4.0 (9)
C6—C1—C2—C3	−0.6 (8)	C23—C20—C21—C22	176.4 (6)
N1—C1—C6—C5	−178.9 (5)	C20—C21—C22—C17	1.9 (9)
C2—C1—C6—C5	1.7 (8)	N3—C24—C25—C26	8.0 (8)
C1—C2—C3—C4	0.2 (8)	N3—C24—C25—C30	−169.8 (5)
C2—C3—C4—C5	−0.9 (8)	C24—C25—C26—C27	−178.0 (5)
C2—C3—C4—C7	−179.5 (5)	C30—C25—C26—C27	0.0 (8)
C3—C4—C5—C6	2.0 (8)	C24—C25—C30—C29	176.9 (5)
C7—C4—C5—C6	−179.3 (5)	C26—C25—C30—C29	−1.0 (8)
C4—C5—C6—C1	−2.5 (8)	C25—C26—C27—C28	1.1 (8)
N1—C8—C9—C10	−8.0 (8)	C26—C27—C28—N4	179.0 (5)
N1—C8—C9—C14	169.9 (5)	C26—C27—C28—C29	−1.1 (8)
C8—C9—C14—C13	−176.9 (5)	N4—C28—C29—C30	180.0 (4)
C8—C9—C10—C11	177.3 (5)	C27—C28—C29—C30	0.1 (8)
C14—C9—C10—C11	−0.7 (7)	C28—C29—C30—C25	0.9 (8)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2A···O2ⁱ	0.86	2.00	2.854 (5)	172
N4—H4···O1ⁱⁱ	0.86	2.06	2.911 (4)	173
C13—H13···O1	0.93	2.40	2.922 (6)	116
C29—H29···O2	0.93	2.35	2.864 (6)	114

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

Experimental details

Crystal data
Chemical formula	C₁₆H₁₆N₂O
M_r	252.31
Crystal system, space group	Triclinic, P1
Temperature (K)	296
a, b, c (Å)	7.1044 (8), 9.7393 (10), 10.9236 (12)
α, β, γ (°)	109.731 (5), 91.799 (6), 100.679 (6)
V (Å³)	695.51 (13)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.08
Crystal size (mm)	0.26 × 0.16 × 0.12

Data collection
Diffractometer	Bruker Kappa APEXII CCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2005)
T_min, T_max	0.980, 0.990
No. of measured, independent and observed [I > 2σ(I)] reflections	10024, 2453, 1460
R_int	0.059
(sin θ/λ)_max (Å⁻¹)	0.596

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.044, 0.112, 0.97
No. of reflections	2453
No. of parameters	339
No. of restraints	3
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.16, −0.15

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2A···O2ⁱ	0.86	2.00	2.854 (5)	172
N4—H4···O1ⁱⁱ	0.86	2.06	2.911 (4)	173
C13—H13···O1	0.93	2.40	2.922 (6)	116
C29—H29···O2	0.93	2.35	2.864 (6)	114

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

Acknowledgements

The authors acknowledge the provision of funds for the purchase of the diffractometer and encouragement by Dr Muhammad Akram Chaudhary, Vice Chancellor, University of Sargodha, Pakistan. The authors also acknowledge the technical support provided by Bana International, Karachi, Pakistan.

References

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