Crystal structure of N1-phenyl-N4-[(quinolin-2-yl)methyl­idene]benzene-1,4-di­amine

Faizi, M.S.H.; Mashrai, A.; Garandal, S.; Shahid, M.

doi:10.1107/S1600536814016006

organic compounds

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ISSN: 2056-9890

Volume 70| Part 9| September 2014| Pages o905-o906

doi:10.1107/S1600536814016006

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Crystal structure of N¹-phenyl-N⁴-[(quinolin-2-yl)methylidene]benzene-1,4-diamine

Md. Serajul Haque Faizi,^a Ashraf Mashrai,^b Saleem Garandal ^c and M. Shahid ^b ^*

^aDepartment of Chemistry, Indian Institute of Technology Kanpur, Kanpur, UP 208 016, India, ^bDepartment of Chemistry, Aligarh Muslim University, Aligarh 202 002, India, and ^cSchool of Chemical Sciences, S.R.T.M. University, Nanded 431 606, India
^*Correspondence e-mail: shahid81chem@gmail.com

Edited by W. T. A. Harrison, University of Aberdeen, Scotland (Received 7 July 2014; accepted 9 July 2014; online 1 August 2014)

In the title compound, C₂₂H₁₇N₃, the dihedral angles between the central benzene ring and the terminal phenyl ring and quinoline ring system (r.m.s. deviation = 0.027 Å) are 44.72 (7) and 9.02 (4)°, respectively, and the bond-angle sum at the amine N atom is 359.9°. In the crystal, the N—H group is not involved in hydrogen bonding and the molecules are linked by weak C—H⋯π interactions, generating [010] chains.

Keywords: crystal structure; quinoline; C—H⋯π interactions.

CCDC reference: 1012864

1. Related literature

For applications of quinoline-containing Schiff bases see: Das et al. (2013 ); Jursic et al. (2002 ); Motswainyana et al. (2013 ); Song et al. (2011 ). The present work is part of an ongoing structural study of Schiff base-metal complexes, see: Faizi & Hussain (2014 ); Faizi & Sen (2014 ); Faizi et al. (2014 ).

2. Experimental

2.1. Crystal data

C₂₂H₁₇N₃
M_r = 323.39
Monoclinic, P 2₁ /c
a = 17.595 (2) Å
b = 7.3348 (8) Å
c = 12.5712 (18) Å
β = 99.769 (6)°
V = 1598.9 (4) Å³
Z = 4
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 100 K
0.29 × 0.21 × 0.15 mm

2.2. Data collection

Bruker SMART APEX CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 2004 ) T_min = 0.967, T_max = 0.984
6866 measured reflections
2964 independent reflections
1557 reflections with I > 2σ(I)
R_int = 0.063

2.3. Refinement

R[F² > 2σ(F²)] = 0.054
wR(F²) = 0.105
S = 0.97
2964 reflections
234 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.22 e Å⁻³
Δρ_min = −0.19 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

Cg1, Cg2 and Cg3 are the centroids of the N1/C1/C6–C9, C1–C6 and C11–C16 rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C7—H7⋯Cg3ⁱ	0.93	2.61	3.430 (2)	148
C12—H12⋯Cg1ⁱ	0.93	2.79	3.536 (2)	138
C13—H13⋯Cg2ⁱ	0.93	2.71	3.508 (3)	145
Symmetry code: (i) $[-x+1, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

Data collection: SMART (Bruker, 2003 ); cell refinement: SAINT (Bruker, 2003); data reduction: SAINT; program(s) used to solve structure: SIR97 (Altomare et al., 1999 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ); molecular graphics: DIAMOND (Brandenberg & Putz, 2006 ); software used to prepare material for publication: DIAMOND.

Supporting information

CCDC reference: 1012864

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536814016006/hb7248sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536814016006/hb7248Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536814016006/hb7248Isup3.cml

checkCIF report

Chemical context top

Quinoline derivatives of Schiff bases are important building blocks of many important compounds widely used in biological applications such as antioxidative and anticancer and fluorescent probe agents in industry and in coordination chemistry (Motswainyana et al., 2013; Das et al., 2013; Song et al., 2011; Jursic et al., 2002). The present work is part of an ongoing structural study of Schiff base metal complexes (Faizi & Hussain, 2014; Faizi & Sen, 2014; Faizi et al. 2014) and we report here the structure of N¹-phenyl-N⁴-[(quinolin-2-yl)methylidene]benzene-1,4-diamine (PQMBD).

Structural commentary top

The synthesis of PQMBD by condensation of 2-quinolinecarboxaldehyde and N-phenyl-p-phenylenediamine has not previously been reported. In the title compound (Fig. 1) PQMBD has non planar structure, the dihedral angle between the quinolinyl and p-phenylenediamine rings is 9.02 (4)° and the dihedral angle between the p-phenylenediamine and N-phenyl rings is 44.72 (7)°. The imine group displays a torsional angle (C9—C10—N2—C11) of 179.20 (2)°.

Supramolecular features top

In the crystal, the N—H group is not involved in hydrogen bonding and the molecules are linked by weak C—H···π interactions, generating [010] chains.

Database survey top

There are very few examples similar to title compound and their metal complex have been reported in the literature (Patra & Goldberg 2003; Gonzalez et al., 2012).

Synthesis and crystallization top

100 mg (1 mmol) of N-phenyl-p-phenylenediamine were dissolved in 10 ml of absolute ethanol. To this solution, 85 mg (1 mmol) of 2-quinolinecarboxaldehyde in 5 ml of absolute ethanol was dropwisely added under stirring. Then, this mixture was stirred for 10 min, two drops of glacial acetic acid were then added and the mixture was further refluxed for 2 h. The resulting yellow precipitate was recovered by filtration, washed several times with a small portions of EtOH and then with diethyl ether to give 150 mg (88%) of the title compound. Yellow blocks were obtained within 3 days by slow evaporation of the MeOH solvent.

Refinement top

Crystal data, data collection and structure refinement details are summarized in Table 1. the N-bound H-atoms were located in difference Fourier maps,and their positions were then held fixed. All H-atoms were positioned geometrically and refined using a riding model with C—H = 0.92–0.93 Å and U_iso(H) = 1.2U_eq(C).

Related literature top

For applications of quinoline-containing Schiff bases see: Das et al. (2013); Jursic et al. (2002); Motswainyana et al. (2013); Song et al. (2011). The present work is part of an ongoing structural study of Schiff base-metal complexes, see: Faizi & Hussain (2014); Faizi & Sen (2014); Faizi et al. (2014).

Computing details top

Data collection: SMART (Bruker, 2003); cell refinement: SAINT (Bruker, 2003); data reduction: SAINT (Bruker, 2003); program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: DIAMOND (Brandenberg & Putz, 2006); software used to prepare material for publication: DIAMOND (Brandenberg & Putz, 2006).

Figures top

Fig. 1. The molecular structure of the title compound, with non-H atoms drawn as 40% probability displacement ellipsoids.

N¹-Phenyl-N⁴-[(quinolin-2-yl)methylidene]benzene-1,4-diamine top

Crystal data top

C₂₂H₁₇N₃	F(000) = 680
M_r = 323.39	D_x = 1.343 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 999 reflections
a = 17.595 (2) Å	θ = 2.6–28.6°
b = 7.3348 (8) Å	µ = 0.08 mm⁻¹
c = 12.5712 (18) Å	T = 100 K
β = 99.769 (6)°	Block, yellow
V = 1598.9 (4) Å³	0.29 × 0.21 × 0.15 mm
Z = 4

Data collection top

Bruker SMART APEX CCD diffractometer	2964 independent reflections
Radiation source: fine-focus sealed tube	1557 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.063
ω–scans	θ_max = 25.5°, θ_min = 2.4°
Absorption correction: multi-scan (SADABS; Sheldrick, 2004)	h = −19→21
T_min = 0.967, T_max = 0.984	k = −8→8
6866 measured reflections	l = −12→15

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)] = 0.054	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.105	H atoms treated by a mixture of independent and constrained refinement
S = 0.97	w = 1/[σ²(F_o²) + (0.033P)²] where P = (F_o² + 2F_c²)/3
2964 reflections	(Δ/σ)_max < 0.001
234 parameters	Δρ_max = 0.22 e Å⁻³
0 restraints	Δρ_min = −0.19 e Å⁻³

Crystal data top

C₂₂H₁₇N₃	V = 1598.9 (4) Å³
M_r = 323.39	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 17.595 (2) Å	µ = 0.08 mm⁻¹
b = 7.3348 (8) Å	T = 100 K
c = 12.5712 (18) Å	0.29 × 0.21 × 0.15 mm
β = 99.769 (6)°

Data collection top

Bruker SMART APEX CCD diffractometer	2964 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 2004)	1557 reflections with I > 2σ(I)
T_min = 0.967, T_max = 0.984	R_int = 0.063
6866 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.054	0 restraints
wR(F²) = 0.105	H atoms treated by a mixture of independent and constrained refinement
S = 0.97	Δρ_max = 0.22 e Å⁻³
2964 reflections	Δρ_min = −0.19 e Å⁻³
234 parameters

Special details top

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
C1	0.25415 (13)	0.2764 (3)	0.16305 (19)	0.0148 (6)
C2	0.18560 (13)	0.3785 (3)	0.1579 (2)	0.0186 (6)
H2	0.1771	0.4464	0.2173	0.022*
C3	0.13189 (14)	0.3776 (3)	0.0660 (2)	0.0209 (6)
H3	0.0869	0.4454	0.0635	0.025*
C4	0.14301 (14)	0.2766 (3)	−0.0251 (2)	0.0215 (7)
H4	0.1059	0.2777	−0.0873	0.026*
C5	0.20884 (14)	0.1767 (3)	−0.0211 (2)	0.0208 (6)
H5	0.2164	0.1100	−0.0813	0.025*
C6	0.26537 (14)	0.1730 (3)	0.07237 (19)	0.0155 (6)
C7	0.33399 (13)	0.0704 (3)	0.08109 (19)	0.0173 (6)
H7	0.3429	−0.0027	0.0240	0.021*
C8	0.38676 (14)	0.0787 (3)	0.1728 (2)	0.0174 (6)
H8	0.4318	0.0101	0.1798	0.021*
C9	0.37258 (14)	0.1929 (3)	0.2577 (2)	0.0157 (6)
C10	0.43043 (15)	0.2137 (3)	0.3554 (2)	0.0163 (6)
C11	0.55486 (14)	0.1692 (3)	0.4537 (2)	0.0138 (6)
C12	0.62578 (13)	0.0883 (3)	0.44931 (19)	0.0179 (6)
H12	0.6325	0.0252	0.3874	0.022*
C13	0.68652 (13)	0.0993 (3)	0.5345 (2)	0.0182 (6)
H13	0.7332	0.0432	0.5296	0.022*
C14	0.67803 (14)	0.1942 (3)	0.62763 (19)	0.0159 (6)
C15	0.60659 (14)	0.2723 (3)	0.6334 (2)	0.0182 (6)
H15	0.5996	0.3345	0.6955	0.022*
C16	0.54638 (13)	0.2585 (3)	0.54833 (19)	0.0180 (6)
H16	0.4990	0.3101	0.5543	0.022*
C17	0.81614 (14)	0.1848 (3)	0.7206 (2)	0.0159 (6)
C18	0.85238 (14)	0.2256 (3)	0.6337 (2)	0.0196 (6)
H18	0.8234	0.2653	0.5691	0.023*
C19	0.93117 (15)	0.2075 (3)	0.6429 (2)	0.0246 (7)
H19	0.9548	0.2354	0.5841	0.030*
C20	0.97548 (15)	0.1486 (3)	0.7378 (2)	0.0286 (7)
H20	1.0285	0.1349	0.7431	0.034*
C21	0.93964 (15)	0.1103 (3)	0.8252 (2)	0.0282 (7)
H21	0.9690	0.0731	0.8901	0.034*
C22	0.86074 (14)	0.1270 (3)	0.8167 (2)	0.0211 (7)
H22	0.8372	0.0993	0.8756	0.025*
N1	0.30802 (11)	0.2868 (2)	0.25571 (15)	0.0160 (5)
N2	0.49805 (11)	0.1482 (2)	0.36031 (15)	0.0165 (5)
N3	0.73653 (12)	0.2067 (3)	0.71688 (18)	0.0206 (6)
H3N	0.7212 (13)	0.233 (3)	0.779 (2)	0.034 (8)*
H10	0.4135 (11)	0.284 (3)	0.4156 (16)	0.016 (6)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0146 (16)	0.0161 (14)	0.0142 (15)	−0.0034 (12)	0.0040 (12)	0.0024 (11)
C2	0.0214 (16)	0.0176 (14)	0.0176 (17)	−0.0046 (12)	0.0052 (13)	0.0003 (12)
C3	0.0174 (16)	0.0222 (15)	0.0226 (18)	0.0018 (12)	0.0021 (13)	0.0023 (13)
C4	0.0190 (17)	0.0225 (15)	0.0204 (17)	−0.0068 (13)	−0.0038 (12)	0.0032 (13)
C5	0.0271 (17)	0.0182 (15)	0.0172 (17)	−0.0056 (13)	0.0041 (13)	−0.0017 (12)
C6	0.0168 (16)	0.0146 (14)	0.0154 (16)	−0.0047 (11)	0.0036 (12)	0.0020 (12)
C7	0.0236 (16)	0.0152 (14)	0.0141 (16)	−0.0031 (12)	0.0063 (13)	−0.0006 (11)
C8	0.0189 (16)	0.0151 (14)	0.0200 (17)	0.0023 (11)	0.0086 (13)	0.0019 (12)
C9	0.0157 (16)	0.0138 (14)	0.0183 (16)	−0.0033 (12)	0.0045 (12)	0.0027 (12)
C10	0.0195 (17)	0.0123 (14)	0.0180 (17)	−0.0002 (12)	0.0056 (13)	−0.0014 (12)
C11	0.0132 (15)	0.0132 (14)	0.0159 (16)	−0.0024 (11)	0.0046 (12)	0.0022 (11)
C12	0.0227 (16)	0.0133 (14)	0.0182 (17)	0.0010 (12)	0.0045 (13)	−0.0013 (11)
C13	0.0141 (16)	0.0167 (14)	0.0236 (18)	0.0053 (11)	0.0027 (13)	0.0018 (12)
C14	0.0180 (16)	0.0155 (14)	0.0134 (16)	−0.0029 (12)	0.0007 (12)	0.0041 (12)
C15	0.0234 (17)	0.0144 (14)	0.0176 (16)	−0.0012 (12)	0.0058 (13)	−0.0013 (11)
C16	0.0160 (16)	0.0205 (15)	0.0190 (16)	−0.0006 (11)	0.0069 (13)	−0.0006 (12)
C17	0.0158 (16)	0.0132 (14)	0.0181 (16)	−0.0023 (11)	0.0007 (12)	−0.0015 (12)
C18	0.0189 (17)	0.0185 (14)	0.0206 (17)	−0.0019 (12)	0.0012 (13)	0.0001 (12)
C19	0.0248 (17)	0.0296 (16)	0.0206 (17)	−0.0071 (13)	0.0070 (13)	−0.0038 (13)
C20	0.0177 (17)	0.0350 (17)	0.033 (2)	−0.0028 (13)	0.0045 (15)	−0.0060 (14)
C21	0.0247 (18)	0.0319 (17)	0.0254 (19)	0.0011 (13)	−0.0031 (14)	−0.0006 (13)
C22	0.0209 (17)	0.0212 (15)	0.0210 (18)	−0.0025 (12)	0.0030 (13)	0.0022 (12)
N1	0.0139 (13)	0.0151 (11)	0.0190 (14)	−0.0002 (10)	0.0026 (10)	0.0026 (9)
N2	0.0152 (13)	0.0157 (12)	0.0179 (14)	−0.0014 (9)	0.0005 (10)	0.0025 (9)
N3	0.0185 (14)	0.0302 (14)	0.0137 (14)	0.0002 (10)	0.0041 (11)	−0.0032 (11)

Geometric parameters (Å, º) top

C1—N1	1.373 (3)	C12—C13	1.381 (3)
C1—C6	1.411 (3)	C12—H12	0.9300
C1—C2	1.412 (3)	C13—C14	1.392 (3)
C2—C3	1.363 (3)	C13—H13	0.9300
C2—H2	0.9300	C14—N3	1.391 (3)
C3—C4	1.405 (3)	C14—C15	1.394 (3)
C3—H3	0.9300	C15—C16	1.375 (3)
C4—C5	1.364 (3)	C15—H15	0.9300
C4—H4	0.9300	C16—H16	0.9300
C5—C6	1.405 (3)	C17—C18	1.387 (3)
C5—H5	0.9300	C17—C22	1.391 (3)
C6—C7	1.411 (3)	C17—N3	1.403 (3)
C7—C8	1.354 (3)	C18—C19	1.378 (3)
C7—H7	0.9300	C18—H18	0.9300
C8—C9	1.412 (3)	C19—C20	1.380 (3)
C8—H8	0.9300	C19—H19	0.9300
C9—N1	1.325 (3)	C20—C21	1.384 (3)
C9—C10	1.464 (3)	C20—H20	0.9300
C10—N2	1.275 (3)	C21—C22	1.380 (3)
C10—H10	1.00 (2)	C21—H21	0.9300
C11—C16	1.388 (3)	C22—H22	0.9300
C11—C12	1.391 (3)	N3—H3N	0.89 (2)
C11—N2	1.415 (3)

N1—C1—C6	123.0 (2)	C12—C13—C14	120.1 (2)
N1—C1—C2	118.1 (2)	C12—C13—H13	119.9
C6—C1—C2	118.9 (2)	C14—C13—H13	119.9
C3—C2—C1	120.0 (2)	N3—C14—C13	122.8 (2)
C3—C2—H2	120.0	N3—C14—C15	118.8 (2)
C1—C2—H2	120.0	C13—C14—C15	118.4 (2)
C2—C3—C4	121.4 (2)	C16—C15—C14	120.8 (2)
C2—C3—H3	119.3	C16—C15—H15	119.6
C4—C3—H3	119.3	C14—C15—H15	119.6
C5—C4—C3	119.2 (2)	C15—C16—C11	121.4 (2)
C5—C4—H4	120.4	C15—C16—H16	119.3
C3—C4—H4	120.4	C11—C16—H16	119.3
C4—C5—C6	121.1 (2)	C18—C17—C22	118.9 (2)
C4—C5—H5	119.4	C18—C17—N3	122.6 (2)
C6—C5—H5	119.4	C22—C17—N3	118.5 (2)
C5—C6—C1	119.3 (2)	C19—C18—C17	120.3 (2)
C5—C6—C7	123.4 (2)	C19—C18—H18	119.9
C1—C6—C7	117.3 (2)	C17—C18—H18	119.9
C8—C7—C6	119.7 (2)	C18—C19—C20	121.0 (3)
C8—C7—H7	120.1	C18—C19—H19	119.5
C6—C7—H7	120.1	C20—C19—H19	119.5
C7—C8—C9	119.2 (2)	C19—C20—C21	118.9 (3)
C7—C8—H8	120.4	C19—C20—H20	120.6
C9—C8—H8	120.4	C21—C20—H20	120.6
N1—C9—C8	123.7 (2)	C22—C21—C20	120.6 (3)
N1—C9—C10	115.7 (2)	C22—C21—H21	119.7
C8—C9—C10	120.6 (2)	C20—C21—H21	119.7
N2—C10—C9	120.8 (2)	C21—C22—C17	120.4 (3)
N2—C10—H10	123.5 (12)	C21—C22—H22	119.8
C9—C10—H10	115.7 (12)	C17—C22—H22	119.8
C16—C11—C12	117.6 (2)	C9—N1—C1	117.0 (2)
C16—C11—N2	126.8 (2)	C10—N2—C11	121.4 (2)
C12—C11—N2	115.6 (2)	C14—N3—C17	128.1 (2)
C13—C12—C11	121.7 (2)	C14—N3—H3N	115.3 (16)
C13—C12—H12	119.1	C17—N3—H3N	116.5 (16)
C11—C12—H12	119.1

N1—C1—C2—C3	177.5 (2)	C13—C14—C15—C16	−1.1 (3)
C6—C1—C2—C3	−0.7 (3)	C14—C15—C16—C11	−1.0 (3)
C1—C2—C3—C4	0.0 (4)	C12—C11—C16—C15	2.2 (3)
C2—C3—C4—C5	0.3 (4)	N2—C11—C16—C15	−179.0 (2)
C3—C4—C5—C6	0.2 (4)	C22—C17—C18—C19	0.5 (3)
C4—C5—C6—C1	−0.9 (3)	N3—C17—C18—C19	177.8 (2)
C4—C5—C6—C7	179.2 (2)	C17—C18—C19—C20	0.1 (4)
N1—C1—C6—C5	−177.0 (2)	C18—C19—C20—C21	−1.0 (4)
C2—C1—C6—C5	1.1 (3)	C19—C20—C21—C22	1.4 (4)
N1—C1—C6—C7	2.9 (3)	C20—C21—C22—C17	−0.8 (4)
C2—C1—C6—C7	−179.0 (2)	C18—C17—C22—C21	−0.1 (3)
C5—C6—C7—C8	177.9 (2)	N3—C17—C22—C21	−177.5 (2)
C1—C6—C7—C8	−2.0 (3)	C8—C9—N1—C1	−2.9 (3)
C6—C7—C8—C9	−1.0 (3)	C10—C9—N1—C1	177.1 (2)
C7—C8—C9—N1	3.7 (3)	C6—C1—N1—C9	−0.5 (3)
C7—C8—C9—C10	−176.3 (2)	C2—C1—N1—C9	−178.6 (2)
N1—C9—C10—N2	−171.1 (2)	C9—C10—N2—C11	179.2 (2)
C8—C9—C10—N2	8.9 (3)	C16—C11—N2—C10	0.0 (3)
C16—C11—C12—C13	−1.5 (3)	C12—C11—N2—C10	178.8 (2)
N2—C11—C12—C13	179.6 (2)	C13—C14—N3—C17	22.2 (4)
C11—C12—C13—C14	−0.5 (3)	C15—C14—N3—C17	−161.0 (2)
C12—C13—C14—N3	178.6 (2)	C18—C17—N3—C14	29.4 (4)
C12—C13—C14—C15	1.8 (3)	C22—C17—N3—C14	−153.2 (2)
N3—C14—C15—C16	−178.0 (2)

Hydrogen-bond geometry (Å, º) top

Cg1, Cg2 and Cg3 are the centroids of the N1/C1/C6–C9, C1–C6 and C11–C16 rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
C7—H7···Cg3ⁱ	0.93	2.61	3.430 (2)	148
C12—H12···Cg1ⁱ	0.93	2.79	3.536 (2)	138
C13—H13···Cg2ⁱ	0.93	2.71	3.508 (3)	145

Symmetry code: (i) −x+1, y−1/2, −z+1/2.

Hydrogen-bond geometry (Å, º) top

Cg1, Cg2 and Cg3 are the centroids of the N1/C1/C6–C9, C1–C6 and C11–C16 rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
C7—H7···Cg3ⁱ	0.93	2.61	3.430 (2)	148
C12—H12···Cg1ⁱ	0.93	2.79	3.536 (2)	138
C13—H13···Cg2ⁱ	0.93	2.71	3.508 (3)	145

Symmetry code: (i) −x+1, y−1/2, −z+1/2.

Acknowledgements

The authors are grateful to the Department of Chemistry, IIT Kanpur, Kanpur-208016, India, for the data collection and Musheer Ahmad for valuable discussions.

References

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Volume 70| Part 9| September 2014| Pages o905-o906

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