6-Phenyl-5a,6,6a,7,12,13a-hexa­hydro-5H-benzo[6,7]indolizino[3,2-a]pyrrolizine

Gunasekaran, B.; Kathiravan, S.; Raghunathan, R.; Renuga, V.; Manivannan, V.

doi:10.1107/S1600536809020091

organic compounds

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ISSN: 2056-9890

Volume 65| Part 7| July 2009| Page o1454

doi:10.1107/S1600536809020091

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6-Phenyl-5a,6,6a,7,12,13a-hexahydro-5H-benzo[6,7]indolizino[3,2-a]pyrrolizine

B. Gunasekaran,^a S. Kathiravan,^b R. Raghunathan,^b V. Renuga ^c and V. Manivannan ^d ^*

^aDepartment of Physics, AMET University, Kanathur, Chennai 603 112, India, ^bDepartment of Organic Chemistry, University of Madras, Guindy Campus, Chennai 600 025, India, ^cDepartment of Chemistry, National College, Thiruchirapalli, Tamil Nadu, India, and ^dDepartment of Research and Development, PRIST University, Vallam, Thanjavur 613 403, Tamil Nadu, India
^*Correspondence e-mail: manivan_1999@yahoo.com

(Received 15 May 2009; accepted 26 May 2009; online 6 June 2009)

In the title compound, C₂₃H₂₂N₂, the central pyrrolidine ring adopts an envelope conformation. The benzene ring of the hexahydropyrroloisoquinoline ring system makes dihedral angles of 83.43 (6) and 61.99 (10)°, respectively, with the phenyl and pyrrole rings. In the crystal structure, weak C—H⋯π interactions are observed.

Related literature

For biological activity of pyrrolidine derivatives, see: Witherup et al. (1995 ); Kravchenko et al. (2005 ). For biological activity of pyrrole derivatives, see: Sobral & Rocha Gonsalves (2001a ,b ); Brockmann & Tour (1995 ); Suslick et al. (1992 ); Di Natale et al. (1998 ). For a related structure, see: Liu et al. (2007 ).

Experimental

Crystal data

C₂₃H₂₂N₂
M_r = 326.43
Monoclinic, P 2₁ /n
a = 14.0694 (14) Å
b = 5.9300 (5) Å
c = 21.177 (2) Å
β = 104.563 (3)°
V = 1710.1 (3) Å³
Z = 4
Mo Kα radiation
μ = 0.07 mm⁻¹
T = 293 K
0.20 × 0.20 × 0.15 mm

Data collection

Bruker Kappa APEXII diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.985, T_max = 0.989
20373 measured reflections
4266 independent reflections
3049 reflections with I > 2σ(I)
R_int = 0.032

Refinement

R[F² > 2σ(F²)] = 0.049
wR(F²) = 0.149
S = 1.01
4266 reflections
226 parameters
H-atom parameters constrained
Δρ_max = 0.17 e Å⁻³
Δρ_min = −0.23 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C4—H4⋯Cg3ⁱ	0.93	2.88	3.7250 (3)	152
C13—H13⋯Cg3ⁱⁱ	0.93	2.94	3.5626 (3)	126
C18—H18B⋯Cg6ⁱⁱⁱ	0.97	2.79	3.6726 (4)	152
Symmetry codes: (i) $[-x+{\script{3\over 2}}, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (ii) -x+1, -y+2, -z+1; (iii) -x+1, -y+1, -z+1. Cg3 and Cg6 are the centroids of the N2/C19–C22 and C11–C16 rings, respectively.

Data collection: APEX2 (Bruker, 2004 ); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009 ); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809020091/is2422sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809020091/is2422Isup2.hkl

checkCIF report

Comment top

Pyrrolidine containing compounds are of significant importance because of their biological activities and widespread employment in catalysis (Witherup et al., 1995; Kravchenko et al., 2005). Pyrroles are very useful precursors in porphyrin synthesis (Sobral & Rocha Gonsalves, 2001a,b) and as monomers for polymer chemistry (Brockmann & Tour, 1995), with applications ranging from non linear optical materials (Suslick et al., 1992) to electronic noses (Di Natale et al., 1998).

The geometric parameters of the title molecule (Fig. 1) agree well with reported similar structure (Liu et al., 2007). The phenyl ring (C11—C16) makes a dihedral angle of 83.43 (6)° with C2—C7 ring and 48.72 (6)° with N2/C19—C22 ring, respectively. The sum of the bond angles around N1 [334.71 (32)°] indicate the sp³ hybridized state of atom N1 in the molecule. The pyrrolidine ring [N1/C9/C10/C17/C23] adopts an envelope conformation.

The crystal structure is stabilized by weak C—H···π [C4—H4···Cg3, C13—H13···Cg3 & C18—H18B···Cg6 (Table 1; Cg3 and Cg6 are the centroid of the rings defined by the atoms N2/C19–C22 and C11–C16, respectively.)] interactions.

Related literature top

For biological activity of pyrrolidine derivatives, see: Witherup et al. (1995); Kravchenko et al. (2005). For biological activity of pyrrole derivatives, see: Sobral & Rocha Gonsalves (2001a,b); Brockmann & Tour (1995); Suslick et al. (1992); Di Natale et al. (1998). For a related structure, see: Liu et al. (2007). Cg3 and Cg6 are the centroids of the N2/C19–C22 and C11–C16 rings, respectively.

Experimental top

A mixture of N-allyl pyrrole-2-carbaldehyde (1 mmol) and 1,2,3,4-tetrahydroisoquinolinic acid (1 mmol) was refluxed in 1,2-dichloro benzene (10 ml) for 12 h till the completion of the reaction as evidenced by TLC analysis. The crude mixture was subjected to column chromatography to get the pure product.

Computing details top

Data collection: APEX2 (Bruker, 2004); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT (Bruker, 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

Fig. 1. The molecular structure of (I), with atom labels and 50% probability displacement ellipsoids for non-H atoms.

6-Phenyl-5a,6,6a,7,12,13a-hexahydro-5H-benzo[6,7]indolizino[3,2- a]pyrrolizine top

Crystal data top

C₂₃H₂₂N₂	F(000) = 696
M_r = 326.43	D_x = 1.268 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 6264 reflections
a = 14.0694 (14) Å	θ = 2.0–28.4°
b = 5.9300 (5) Å	µ = 0.07 mm⁻¹
c = 21.177 (2) Å	T = 293 K
β = 104.563 (3)°	Needle, yellow
V = 1710.1 (3) Å³	0.20 × 0.20 × 0.15 mm
Z = 4

Data collection top

Bruker KappaAPEXII diffractometer	4266 independent reflections
Radiation source: fine-focus sealed tube	3049 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.032
Detector resolution: 0 pixels mm^-1	θ_max = 28.4°, θ_min = 2.0°
ω and ϕ scans	h = −18→17
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	k = −7→4
T_min = 0.985, T_max = 0.989	l = −28→28
20373 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)] = 0.049	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.149	H-atom parameters constrained
S = 1.01	w = 1/[σ²(F_o²) + (0.0757P)² + 0.3733P] where P = (F_o² + 2F_c²)/3
4266 reflections	(Δ/σ)_max < 0.001
226 parameters	Δρ_max = 0.17 e Å⁻³
0 restraints	Δρ_min = −0.23 e Å⁻³

Crystal data top

C₂₃H₂₂N₂	V = 1710.1 (3) Å³
M_r = 326.43	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 14.0694 (14) Å	µ = 0.07 mm⁻¹
b = 5.9300 (5) Å	T = 293 K
c = 21.177 (2) Å	0.20 × 0.20 × 0.15 mm
β = 104.563 (3)°

Data collection top

Bruker KappaAPEXII diffractometer	4266 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	3049 reflections with I > 2σ(I)
T_min = 0.985, T_max = 0.989	R_int = 0.032
20373 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.049	0 restraints
wR(F²) = 0.149	H-atom parameters constrained
S = 1.01	Δρ_max = 0.17 e Å⁻³
4266 reflections	Δρ_min = −0.23 e Å⁻³
226 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
N1	0.42095 (9)	0.02857 (19)	0.64155 (6)	0.0319 (3)
N2	0.26180 (10)	0.2368 (2)	0.50434 (6)	0.0447 (3)
C9	0.42973 (10)	0.2650 (2)	0.66188 (7)	0.0308 (3)
H9	0.3639	0.3302	0.6548	0.037*
C2	0.38439 (10)	−0.0647 (2)	0.74598 (7)	0.0353 (3)
C8	0.48113 (11)	0.2811 (3)	0.73313 (7)	0.0380 (3)
H8A	0.4760	0.4343	0.7480	0.046*
H8B	0.5502	0.2470	0.7390	0.046*
C10	0.48203 (10)	0.3722 (2)	0.61376 (7)	0.0347 (3)
H10	0.4648	0.5326	0.6095	0.042*
C1	0.35781 (11)	−0.0995 (2)	0.67344 (7)	0.0367 (3)
H1A	0.3630	−0.2586	0.6642	0.044*
H1B	0.2901	−0.0542	0.6556	0.044*
C23	0.39150 (11)	0.0267 (2)	0.56953 (7)	0.0348 (3)
H23	0.4220	−0.1011	0.5528	0.042*
C17	0.43198 (12)	0.2536 (3)	0.54943 (8)	0.0400 (4)
H17	0.4796	0.2248	0.5236	0.048*
C7	0.43830 (10)	0.1217 (2)	0.77408 (7)	0.0357 (3)
C11	0.59247 (11)	0.3523 (2)	0.63345 (7)	0.0375 (3)
C6	0.45606 (12)	0.1552 (3)	0.84096 (8)	0.0476 (4)
H6	0.4907	0.2820	0.8598	0.057*
C22	0.28437 (11)	0.0379 (3)	0.53632 (7)	0.0392 (3)
C3	0.35068 (12)	−0.2155 (3)	0.78562 (8)	0.0479 (4)
H3	0.3141	−0.3403	0.7671	0.057*
C12	0.64174 (12)	0.1645 (3)	0.61992 (8)	0.0472 (4)
H12	0.6062	0.0414	0.5991	0.057*
C14	0.79640 (14)	0.3355 (4)	0.66854 (11)	0.0724 (6)
H14	0.8647	0.3305	0.6796	0.087*
C5	0.42305 (13)	0.0033 (4)	0.87978 (8)	0.0555 (5)
H5	0.4362	0.0266	0.9246	0.067*
C16	0.64758 (13)	0.5309 (3)	0.66614 (9)	0.0531 (4)
H16	0.6158	0.6585	0.6762	0.064*
C4	0.37077 (14)	−0.1825 (4)	0.85217 (9)	0.0573 (5)
H4	0.3489	−0.2863	0.8783	0.069*
C21	0.19983 (13)	−0.0869 (3)	0.52436 (8)	0.0544 (5)
H21	0.1929	−0.2310	0.5399	0.065*
C20	0.12558 (14)	0.0442 (4)	0.48407 (9)	0.0637 (6)
H20	0.0603	0.0017	0.4683	0.076*
C19	0.16540 (13)	0.2435 (4)	0.47212 (9)	0.0579 (5)
H19	0.1329	0.3616	0.4468	0.069*
C18	0.34333 (14)	0.3849 (3)	0.50884 (10)	0.0663 (6)
H18A	0.3341	0.5246	0.5304	0.080*
H18B	0.3520	0.4195	0.4659	0.080*
C13	0.74311 (14)	0.1569 (4)	0.63685 (10)	0.0634 (5)
H13	0.7754	0.0302	0.6267	0.076*
C15	0.74889 (15)	0.5212 (4)	0.68388 (11)	0.0696 (6)
H15	0.7849	0.6409	0.7063	0.084*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N1	0.0392 (6)	0.0291 (6)	0.0299 (6)	−0.0006 (5)	0.0136 (5)	0.0012 (4)
N2	0.0475 (8)	0.0488 (8)	0.0345 (7)	−0.0014 (6)	0.0043 (6)	0.0001 (6)
C9	0.0322 (7)	0.0279 (6)	0.0335 (8)	0.0011 (5)	0.0103 (6)	0.0010 (5)
C2	0.0359 (7)	0.0397 (7)	0.0328 (8)	0.0054 (6)	0.0133 (6)	0.0054 (6)
C8	0.0399 (8)	0.0399 (8)	0.0338 (8)	−0.0039 (6)	0.0085 (6)	−0.0013 (6)
C10	0.0406 (8)	0.0294 (7)	0.0356 (8)	−0.0011 (5)	0.0127 (6)	0.0035 (5)
C1	0.0450 (8)	0.0321 (7)	0.0358 (8)	−0.0041 (6)	0.0157 (6)	0.0006 (6)
C23	0.0443 (8)	0.0327 (7)	0.0314 (7)	−0.0013 (6)	0.0167 (6)	−0.0013 (5)
C17	0.0456 (8)	0.0423 (8)	0.0343 (8)	−0.0065 (6)	0.0143 (7)	0.0043 (6)
C7	0.0325 (7)	0.0436 (8)	0.0317 (8)	0.0064 (6)	0.0095 (6)	0.0033 (6)
C11	0.0399 (8)	0.0385 (8)	0.0373 (8)	−0.0059 (6)	0.0158 (6)	0.0057 (6)
C6	0.0465 (9)	0.0617 (10)	0.0339 (8)	−0.0002 (7)	0.0086 (7)	−0.0013 (7)
C22	0.0477 (9)	0.0414 (8)	0.0305 (7)	−0.0066 (6)	0.0132 (6)	−0.0036 (6)
C3	0.0492 (9)	0.0544 (10)	0.0439 (9)	−0.0047 (7)	0.0187 (8)	0.0083 (7)
C12	0.0464 (9)	0.0467 (9)	0.0530 (10)	−0.0005 (7)	0.0210 (8)	0.0029 (7)
C14	0.0384 (10)	0.1029 (18)	0.0768 (15)	−0.0080 (11)	0.0159 (10)	0.0205 (13)
C5	0.0539 (10)	0.0837 (13)	0.0305 (8)	0.0026 (9)	0.0138 (7)	0.0060 (8)
C16	0.0524 (10)	0.0499 (10)	0.0568 (11)	−0.0141 (8)	0.0136 (8)	−0.0027 (8)
C4	0.0572 (11)	0.0792 (13)	0.0411 (10)	−0.0012 (9)	0.0227 (8)	0.0172 (9)
C21	0.0581 (11)	0.0679 (12)	0.0391 (9)	−0.0228 (9)	0.0157 (8)	−0.0059 (8)
C20	0.0449 (10)	0.1055 (17)	0.0405 (10)	−0.0142 (10)	0.0105 (8)	−0.0098 (10)
C19	0.0474 (10)	0.0791 (13)	0.0413 (10)	0.0060 (9)	0.0006 (8)	−0.0050 (9)
C18	0.0655 (12)	0.0555 (11)	0.0623 (12)	−0.0168 (9)	−0.0126 (10)	0.0245 (9)
C13	0.0515 (11)	0.0744 (13)	0.0722 (14)	0.0120 (9)	0.0303 (10)	0.0125 (10)
C15	0.0526 (11)	0.0799 (14)	0.0719 (14)	−0.0276 (11)	0.0074 (10)	0.0018 (11)

Geometric parameters (Å, º) top

N1—C1	1.4574 (17)	C11—C12	1.380 (2)
N1—C9	1.4625 (17)	C11—C16	1.390 (2)
N1—C23	1.4764 (18)	C6—C5	1.377 (2)
N2—C19	1.357 (2)	C6—H6	0.9300
N2—C22	1.358 (2)	C22—C21	1.369 (2)
N2—C18	1.429 (2)	C3—C4	1.380 (2)
C9—C8	1.503 (2)	C3—H3	0.9300
C9—C10	1.5366 (19)	C12—C13	1.381 (2)
C9—H9	0.9800	C12—H12	0.9300
C2—C7	1.387 (2)	C14—C15	1.369 (3)
C2—C3	1.389 (2)	C14—C13	1.372 (3)
C2—C1	1.501 (2)	C14—H14	0.9300
C8—C7	1.507 (2)	C5—C4	1.371 (3)
C8—H8A	0.9700	C5—H5	0.9300
C8—H8B	0.9700	C16—C15	1.381 (3)
C10—C11	1.509 (2)	C16—H16	0.9300
C10—C17	1.537 (2)	C4—H4	0.9300
C10—H10	0.9800	C21—C20	1.405 (3)
C1—H1A	0.9700	C21—H21	0.9300
C1—H1B	0.9700	C20—C19	1.359 (3)
C23—C22	1.496 (2)	C20—H20	0.9300
C23—C17	1.561 (2)	C19—H19	0.9300
C23—H23	0.9800	C18—H18A	0.9700
C17—C18	1.537 (2)	C18—H18B	0.9700
C17—H17	0.9800	C13—H13	0.9300
C7—C6	1.389 (2)	C15—H15	0.9300

C1—N1—C9	112.29 (11)	C12—C11—C16	118.18 (15)
C1—N1—C23	115.43 (11)	C12—C11—C10	122.81 (14)
C9—N1—C23	106.99 (10)	C16—C11—C10	119.01 (14)
C19—N2—C22	110.79 (15)	C5—C6—C7	120.94 (17)
C19—N2—C18	134.42 (16)	C5—C6—H6	119.5
C22—N2—C18	114.69 (14)	C7—C6—H6	119.5
N1—C9—C8	109.89 (11)	N2—C22—C21	107.09 (15)
N1—C9—C10	102.73 (11)	N2—C22—C23	110.77 (13)
C8—C9—C10	116.72 (12)	C21—C22—C23	142.08 (16)
N1—C9—H9	109.1	C4—C3—C2	120.85 (17)
C8—C9—H9	109.1	C4—C3—H3	119.6
C10—C9—H9	109.1	C2—C3—H3	119.6
C7—C2—C3	119.11 (14)	C11—C12—C13	120.81 (17)
C7—C2—C1	121.14 (12)	C11—C12—H12	119.6
C3—C2—C1	119.67 (14)	C13—C12—H12	119.6
C9—C8—C7	112.12 (12)	C15—C14—C13	119.86 (18)
C9—C8—H8A	109.2	C15—C14—H14	120.1
C7—C8—H8A	109.2	C13—C14—H14	120.1
C9—C8—H8B	109.2	C4—C5—C6	119.76 (16)
C7—C8—H8B	109.2	C4—C5—H5	120.1
H8A—C8—H8B	107.9	C6—C5—H5	120.1
C11—C10—C9	114.59 (11)	C15—C16—C11	120.79 (19)
C11—C10—C17	114.82 (12)	C15—C16—H16	119.6
C9—C10—C17	102.09 (11)	C11—C16—H16	119.6
C11—C10—H10	108.3	C5—C4—C3	119.97 (16)
C9—C10—H10	108.3	C5—C4—H4	120.0
C17—C10—H10	108.3	C3—C4—H4	120.0
N1—C1—C2	112.25 (12)	C22—C21—C20	106.99 (17)
N1—C1—H1A	109.2	C22—C21—H21	126.5
C2—C1—H1A	109.2	C20—C21—H21	126.5
N1—C1—H1B	109.2	C19—C20—C21	108.40 (17)
C2—C1—H1B	109.2	C19—C20—H20	125.8
H1A—C1—H1B	107.9	C21—C20—H20	125.8
N1—C23—C22	118.24 (11)	N2—C19—C20	106.73 (17)
N1—C23—C17	104.38 (11)	N2—C19—H19	126.6
C22—C23—C17	103.13 (12)	C20—C19—H19	126.6
N1—C23—H23	110.2	N2—C18—C17	104.54 (13)
C22—C23—H23	110.2	N2—C18—H18A	110.8
C17—C23—H23	110.2	C17—C18—H18A	110.8
C18—C17—C10	112.99 (14)	N2—C18—H18B	110.8
C18—C17—C23	106.78 (13)	C17—C18—H18B	110.8
C10—C17—C23	105.64 (11)	H18A—C18—H18B	108.9
C18—C17—H17	110.4	C14—C13—C12	120.24 (19)
C10—C17—H17	110.4	C14—C13—H13	119.9
C23—C17—H17	110.4	C12—C13—H13	119.9
C2—C7—C6	119.35 (14)	C14—C15—C16	120.1 (2)
C2—C7—C8	120.50 (13)	C14—C15—H15	120.0
C6—C7—C8	120.09 (14)	C16—C15—H15	120.0

C1—N1—C9—C8	65.15 (15)	C17—C10—C11—C16	146.25 (14)
C23—N1—C9—C8	−167.22 (11)	C2—C7—C6—C5	1.6 (2)
C1—N1—C9—C10	−169.97 (11)	C8—C7—C6—C5	−175.69 (15)
C23—N1—C9—C10	−42.33 (13)	C19—N2—C22—C21	−0.11 (19)
N1—C9—C8—C7	−48.57 (15)	C18—N2—C22—C21	−177.00 (16)
C10—C9—C8—C7	−164.97 (12)	C19—N2—C22—C23	177.62 (13)
N1—C9—C10—C11	−84.82 (14)	C18—N2—C22—C23	0.7 (2)
C8—C9—C10—C11	35.46 (17)	N1—C23—C22—N2	112.17 (14)
N1—C9—C10—C17	39.94 (13)	C17—C23—C22—N2	−2.34 (15)
C8—C9—C10—C17	160.22 (12)	N1—C23—C22—C21	−71.4 (3)
C9—N1—C1—C2	−49.38 (16)	C17—C23—C22—C21	174.1 (2)
C23—N1—C1—C2	−172.38 (11)	C7—C2—C3—C4	−0.4 (2)
C7—C2—C1—N1	20.18 (19)	C1—C2—C3—C4	−177.42 (15)
C3—C2—C1—N1	−162.92 (13)	C16—C11—C12—C13	−1.7 (2)
C1—N1—C23—C22	38.60 (17)	C10—C11—C12—C13	177.70 (15)
C9—N1—C23—C22	−87.17 (14)	C7—C6—C5—C4	−0.8 (3)
C1—N1—C23—C17	152.43 (12)	C12—C11—C16—C15	0.7 (3)
C9—N1—C23—C17	26.66 (14)	C10—C11—C16—C15	−178.73 (16)
C11—C10—C17—C18	−142.72 (14)	C6—C5—C4—C3	−0.6 (3)
C9—C10—C17—C18	92.68 (14)	C2—C3—C4—C5	1.3 (3)
C11—C10—C17—C23	100.90 (14)	N2—C22—C21—C20	−0.04 (19)
C9—C10—C17—C23	−23.71 (14)	C23—C22—C21—C20	−176.58 (19)
N1—C23—C17—C18	−121.16 (14)	C22—C21—C20—C19	0.2 (2)
C22—C23—C17—C18	3.00 (16)	C22—N2—C19—C20	0.2 (2)
N1—C23—C17—C10	−0.62 (14)	C18—N2—C19—C20	176.3 (2)
C22—C23—C17—C10	123.53 (12)	C21—C20—C19—N2	−0.2 (2)
C3—C2—C7—C6	−1.0 (2)	C19—N2—C18—C17	−174.65 (17)
C1—C2—C7—C6	175.95 (13)	C22—N2—C18—C17	1.3 (2)
C3—C2—C7—C8	176.34 (14)	C10—C17—C18—N2	−118.36 (16)
C1—C2—C7—C8	−6.7 (2)	C23—C17—C18—N2	−2.7 (2)
C9—C8—C7—C2	20.92 (19)	C15—C14—C13—C12	0.5 (3)
C9—C8—C7—C6	−161.79 (13)	C11—C12—C13—C14	1.2 (3)
C9—C10—C11—C12	84.56 (17)	C13—C14—C15—C16	−1.5 (3)
C17—C10—C11—C12	−33.18 (19)	C11—C16—C15—C14	0.9 (3)
C9—C10—C11—C16	−96.00 (16)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C4—H4···Cg3ⁱ	0.93	2.88	3.7250 (3)	152
C13—H13···Cg3ⁱⁱ	0.93	2.94	3.5626 (3)	126
C18—H18B···Cg6ⁱⁱⁱ	0.97	2.79	3.6726 (4)	152

Symmetry codes: (i) −x+3/2, y+1/2, −z+1/2; (ii) −x+1, −y+2, −z+1; (iii) −x+1, −y+1, −z+1.

Experimental details

Crystal data
Chemical formula	C₂₃H₂₂N₂
M_r	326.43
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	293
a, b, c (Å)	14.0694 (14), 5.9300 (5), 21.177 (2)
β (°)	104.563 (3)
V (Å³)	1710.1 (3)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.07
Crystal size (mm)	0.20 × 0.20 × 0.15

Data collection
Diffractometer	Bruker KappaAPEXII diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.985, 0.989
No. of measured, independent and observed [I > 2σ(I)] reflections	20373, 4266, 3049
R_int	0.032
(sin θ/λ)_max (Å⁻¹)	0.669

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.049, 0.149, 1.01
No. of reflections	4266
No. of parameters	226
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.17, −0.23

Computer programs: APEX2 (Bruker, 2004), SAINT (Bruker, 2004), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C4—H4···Cg3ⁱ	0.93	2.88	3.7250 (3)	152
C13—H13···Cg3ⁱⁱ	0.93	2.94	3.5626 (3)	126
C18—H18B···Cg6ⁱⁱⁱ	0.97	2.79	3.6726 (4)	152

Symmetry codes: (i) −x+3/2, y+1/2, −z+1/2; (ii) −x+1, −y+2, −z+1; (iii) −x+1, −y+1, −z+1.

Acknowledgements

The authors thank AMET University management, India, for their kind support.

References

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