6-Methyl-2,7-diphenyl-1,4-diazepan-5-one

Kumar, S.S.; Kavitha, H.P.; Vennila, J.P.; Chakkaravarthi, G.; Manivannan, V.

doi:10.1107/S1600536809049630

organic compounds

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ISSN: 2056-9890

Volume 65| Part 12| December 2009| Page o3211

doi:10.1107/S1600536809049630

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6-Methyl-2,7-diphenyl-1,4-diazepan-5-one

S. Sathish Kumar,^a Helen P. Kavitha,^a Jasmine P. Vennila,^b G. Chakkaravarthi ^c and V. Manivannan ^d ^*

^aDepartment of Chemistry, SRM University, Ramapuram Campus, Chennai 600 089, India, ^bDepartment of Physics, Panimalar Institute of Technology, Chennai 602103, Tamil Nadu, India, ^cDepartment of Physics, CPCL Polytechnic College, Chennai 600 068, India, and ^dDepartment of Research and Development, PRIST University, Vallam, Thanjavur 613 403, Tamil Nadu, India
^*Correspondence e-mail: manivan_1999@yahoo.com

(Received 11 October 2009; accepted 19 November 2009; online 25 November 2009)

The title compound, C₁₈H₂₀N₂O, crystallizes with two molecules in the asymmetric unit. The seven-membered ring in both molecules adopts a distorted chair conformation. The dihedral angles between the phenyl rings are 43.2 (1) and 54.7 (1)° in the two molecules. The crystal packing features N—H⋯O and weak N—H⋯π and C—H⋯π interactions.

Related literature

For the biological activity of related compounds, see: Gopalakrishnan et al. (2007 ); Wlodarczyk et al. (2006 ). For the synthetic procedure, see: Thennarasu & Perumal (2002 ). For hydrogen-bond motifs, see: Bernstein et al. (1995 ).

Experimental

Crystal data

C₁₈H₂₀N₂O
M_r = 280.36
Monoclinic, P 2₁ /c
a = 10.8621 (3) Å
b = 21.3210 (7) Å
c = 13.3890 (4) Å
β = 91.167 (2)°
V = 3100.13 (16) Å³
Z = 8
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 295 K
0.26 × 0.22 × 0.18 mm

Data collection

Bruker Kappa APEXII diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.981, T_max = 0.987
32883 measured reflections
7003 independent reflections
4175 reflections with I > 2σ(I)
R_int = 0.034

Refinement

R[F² > 2σ(F²)] = 0.049
wR(F²) = 0.150
S = 1.01
7003 reflections
397 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.26 e Å⁻³
Δρ_min = −0.18 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2A⋯O2ⁱ	0.90 (2)	2.02 (2)	2.911 (2)	170.2 (18)
N4—H4A⋯O1ⁱ	0.87 (2)	2.03 (2)	2.884 (2)	167 (2)
N1—H1A⋯Cg1ⁱⁱ	0.88 (2)	2.93 (2)	3.707 (2)	149.5 (2)
C18—H18⋯Cg5ⁱⁱⁱ	0.93	2.95	3.872 (2)	171
Symmetry codes: (i) -x, -y, -z+1; (ii) -x, -y, -z; (iii) x+1, y, z. Cg1 and Cg5 are the centroids of the C1–C6 and C31–C36 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/S1600536809049630/gk2234sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809049630/gk2234Isup2.hkl

checkCIF report

Comment top

In view of the biological activities of the heterocyclic compounds with 1,4-diazepan-5-one fragment that have widespread applications in pharmaceuticals (Wlodarczyk et al., 2006; Gopalakrishnan et al., 2007), we report the crystal structure of the title compound.

In the molecule A atoms C7, C8 and C9 show S-configuration whereas in the enatiomeric molecule B atoms C25, C26 and C27 show R-configuration. The phenyl ring C1—C6 forms the dihedral angle of 43.2 (1)° with the phenyl ring C13—C18 in molecule A and the phenyl ring C19—C24 forms the dihedral angle of 54.7 (1) ° with the phenyl ring C31—C36 in molecule B. Intermolecular N—H··· O interactions between the two symmetry independent molecules generates an eight-membered ring with graph-set motif R₂²(8) (Bernstein et al., 1995). The crystal packing is controlled by weak N—H··· O, N—H···π and C—H···π interactions (see Table 1 & Fig. 2).

Related literature top

For the biological activity of related compounds, see: Gopalakrishnan et al. (2007); Wlodarczyk et al. (2006). For the synthetic procedure, see: Thennarasu & Perumal (2002). For hydrogen-bond motifs, see: Bernstein et al. (1995). Cg1 and Cg5 are the centroids of the C1–C6 and C31–C36 rings, respectively.

Experimental top

The title compound was prepared according to the general procedure reported by Thennarasu & Perumal (2002). 3-Methyl-2,6-diphenylpiperidin-4-one (1.82 g, 5 mmole) was added into the ice cold sulfuric acid and the mixture was allowed to reach the room temperature. Then, sodium azide (1.92 g, 30 mmole) was added in portions over a period of one hour. The solution was then poured into crushed ice. The pH of the solution was adjusted to approximately 8.0 using 2 N NaOH solution. The precipitated white solid was recrystallized from ethanol to yield colourless diffraction quality crystals.

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 the title compound, with atom labels and 30% probability displacement ellipsoids for non-H atoms. A and B are the two molecules in the asymmetric unit.
	Fig. 2. Intermolecular N—H···O interactions - view down the b axis. Hydrogen bonds are shown as dashed lines. H atoms not involved in hydrogen bonding have been omitted.

6-Methyl-2,7-diphenyl-1,4-diazepan-5-one top

Crystal data top

C₁₈H₂₀N₂O	F(000) = 1200
M_r = 280.36	D_x = 1.201 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2786 reflections
a = 10.8621 (3) Å	θ = 1.9–27.4°
b = 21.3210 (7) Å	µ = 0.08 mm⁻¹
c = 13.3890 (4) Å	T = 295 K
β = 91.167 (2)°	Block, colourless
V = 3100.13 (16) Å³	0.26 × 0.22 × 0.18 mm
Z = 8

Data collection top

Bruker Kappa APEXII diffractometer	7003 independent reflections
Radiation source: fine-focus sealed tube	4175 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.034
ω and ϕ scans	θ_max = 27.4°, θ_min = 1.9°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −14→13
T_min = 0.981, T_max = 0.987	k = −27→27
32883 measured reflections	l = −17→17

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) = 0.150	H atoms treated by a mixture of independent and constrained refinement
S = 1.01	w = 1/[σ²(F_o²) + (0.0613P)² + 0.757P] where P = (F_o² + 2F_c²)/3
7003 reflections	(Δ/σ)_max < 0.001
397 parameters	Δρ_max = 0.26 e Å⁻³
1 restraint	Δρ_min = −0.18 e Å⁻³

Crystal data top

C₁₈H₂₀N₂O	V = 3100.13 (16) Å³
M_r = 280.36	Z = 8
Monoclinic, P2₁/c	Mo Kα radiation
a = 10.8621 (3) Å	µ = 0.08 mm⁻¹
b = 21.3210 (7) Å	T = 295 K
c = 13.3890 (4) Å	0.26 × 0.22 × 0.18 mm
β = 91.167 (2)°

Data collection top

Bruker Kappa APEXII diffractometer	7003 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	4175 reflections with I > 2σ(I)
T_min = 0.981, T_max = 0.987	R_int = 0.034
32883 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.049	1 restraint
wR(F²) = 0.150	H atoms treated by a mixture of independent and constrained refinement
S = 1.01	Δρ_max = 0.26 e Å⁻³
7003 reflections	Δρ_min = −0.18 e Å⁻³
397 parameters

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
C1	−0.05795 (17)	−0.04801 (8)	0.11713 (12)	0.0485 (4)
C2	−0.0143 (2)	−0.10676 (9)	0.09516 (15)	0.0678 (6)
H2	0.0593	−0.1202	0.1245	0.081*
C3	−0.0773 (3)	−0.14624 (10)	0.03052 (16)	0.0795 (7)
H3	−0.0463	−0.1860	0.0173	0.095*
C4	−0.1837 (2)	−0.12746 (12)	−0.01365 (17)	0.0785 (7)
H4	−0.2269	−0.1543	−0.0565	0.094*
C5	−0.2275 (2)	−0.06876 (13)	0.00506 (18)	0.0847 (7)
H5	−0.2998	−0.0552	−0.0264	0.102*
C6	−0.16502 (19)	−0.02932 (11)	0.07031 (16)	0.0687 (6)
H6	−0.1961	0.0105	0.0826	0.082*
C7	0.01134 (17)	−0.00817 (8)	0.19307 (12)	0.0473 (4)
H7	0.0991	−0.0087	0.1775	0.057*
C8	0.03251 (17)	0.10337 (7)	0.24911 (12)	0.0463 (4)
H8	0.1206	0.1007	0.2351	0.056*
C9	0.01501 (17)	0.09158 (8)	0.36136 (12)	0.0493 (4)
H9	−0.0702	0.0782	0.3712	0.059*
C10	0.09125 (18)	−0.01783 (8)	0.37215 (13)	0.0526 (4)
C11	−0.00555 (19)	−0.03663 (8)	0.29722 (13)	0.0549 (5)
H11A	−0.0853	−0.0241	0.3216	0.066*
H11B	−0.0056	−0.0820	0.2914	0.066*
C12	0.0399 (2)	0.14835 (9)	0.42625 (14)	0.0662 (6)
H12A	0.0341	0.1368	0.4953	0.099*
H12B	−0.0197	0.1804	0.4108	0.099*
H12C	0.1210	0.1640	0.4139	0.099*
C13	−0.01396 (17)	0.16719 (8)	0.21681 (12)	0.0476 (4)
C14	−0.13663 (18)	0.17781 (9)	0.19508 (14)	0.0562 (5)
H14	−0.1928	0.1451	0.1998	0.067*
C15	−0.1770 (2)	0.23685 (9)	0.16622 (15)	0.0643 (5)
H15	−0.2601	0.2436	0.1522	0.077*
C16	−0.0951 (2)	0.28531 (9)	0.15823 (15)	0.0663 (6)
H16	−0.1222	0.3248	0.1383	0.080*
C17	0.0266 (2)	0.27512 (9)	0.17977 (15)	0.0637 (5)
H17	0.0825	0.3079	0.1747	0.076*
C18	0.06729 (18)	0.21665 (8)	0.20889 (14)	0.0556 (5)
H18	0.1505	0.2104	0.2234	0.067*
C19	−0.57859 (17)	−0.06524 (9)	0.20328 (13)	0.0528 (4)
C20	−0.5541 (3)	−0.05228 (12)	0.10529 (16)	0.0890 (8)
H20	−0.5076	−0.0171	0.0896	0.107*
C21	−0.5974 (3)	−0.09052 (13)	0.03036 (18)	0.1049 (9)
H21	−0.5814	−0.0806	−0.0357	0.126*
C22	−0.6634 (2)	−0.14265 (12)	0.05125 (19)	0.0848 (7)
H22	−0.6910	−0.1690	0.0001	0.102*
C23	−0.6884 (2)	−0.15582 (11)	0.14736 (19)	0.0822 (7)
H23	−0.7340	−0.1914	0.1625	0.099*
C24	−0.6472 (2)	−0.11726 (10)	0.22268 (16)	0.0685 (6)
H24	−0.6664	−0.1267	0.2884	0.082*
C25	−0.52358 (17)	−0.02607 (8)	0.28651 (13)	0.0519 (4)
H25	−0.5652	−0.0359	0.3489	0.062*
C26	−0.51055 (17)	0.08491 (8)	0.34472 (14)	0.0545 (5)
H26	−0.5551	0.0724	0.4044	0.065*
C27	−0.37168 (17)	0.08639 (8)	0.36986 (14)	0.0534 (4)
H27	−0.3269	0.0873	0.3071	0.064*
C28	−0.32986 (17)	−0.02759 (9)	0.39725 (14)	0.0557 (5)
C29	−0.38718 (18)	−0.04257 (9)	0.29788 (14)	0.0602 (5)
H29A	−0.3775	−0.0871	0.2855	0.072*
H29B	−0.3424	−0.0203	0.2469	0.072*
C30	−0.3340 (2)	0.14317 (10)	0.43108 (18)	0.0744 (6)
H30A	−0.3845	0.1460	0.4889	0.112*
H30B	−0.3442	0.1804	0.3914	0.112*
H30C	−0.2492	0.1392	0.4518	0.112*
C31	−0.55368 (18)	0.14851 (10)	0.31237 (19)	0.0691 (6)
C32	−0.5286 (2)	0.17105 (11)	0.2185 (2)	0.0944 (8)
H32	−0.4888	0.1454	0.1731	0.113*
C33	−0.5619 (3)	0.23130 (17)	0.1909 (4)	0.1510 (17)
H33	−0.5456	0.2459	0.1271	0.181*
C34	−0.6192 (4)	0.26937 (18)	0.2584 (6)	0.180 (3)
H34	−0.6395	0.3104	0.2413	0.216*
C35	−0.6460 (3)	0.24657 (18)	0.3505 (5)	0.161 (2)
H35	−0.6870	0.2720	0.3954	0.193*
C36	−0.6138 (2)	0.18703 (12)	0.3781 (3)	0.1021 (10)
H36	−0.6324	0.1724	0.4414	0.122*
N1	−0.03260 (15)	0.05628 (7)	0.18881 (11)	0.0518 (4)
N2	0.09714 (16)	0.04195 (7)	0.39814 (11)	0.0550 (4)
N3	−0.53901 (17)	0.04046 (7)	0.26410 (12)	0.0566 (4)
N4	−0.33046 (16)	0.03138 (8)	0.42746 (12)	0.0571 (4)
O1	0.16394 (14)	−0.05709 (6)	0.40701 (10)	0.0724 (4)
O2	−0.28387 (14)	−0.06962 (6)	0.44918 (11)	0.0751 (4)
H1A	−0.0273 (17)	0.0686 (9)	0.1266 (15)	0.060 (6)*
H2A	0.1588 (18)	0.0538 (9)	0.4403 (15)	0.065 (6)*
H3A	−0.616 (2)	0.0465 (10)	0.2477 (16)	0.077 (7)*
H4A	−0.291 (2)	0.0403 (10)	0.4827 (17)	0.073 (7)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0583 (11)	0.0441 (10)	0.0432 (9)	−0.0040 (8)	0.0021 (8)	0.0013 (7)
C2	0.0880 (16)	0.0517 (12)	0.0632 (12)	0.0099 (10)	−0.0133 (11)	−0.0067 (9)
C3	0.120 (2)	0.0524 (13)	0.0659 (13)	−0.0023 (13)	−0.0062 (13)	−0.0130 (10)
C4	0.0900 (17)	0.0830 (17)	0.0627 (13)	−0.0259 (14)	0.0033 (12)	−0.0208 (12)
C5	0.0633 (14)	0.111 (2)	0.0794 (15)	−0.0023 (13)	−0.0112 (11)	−0.0298 (14)
C6	0.0635 (13)	0.0708 (14)	0.0713 (13)	0.0067 (10)	−0.0083 (10)	−0.0169 (11)
C7	0.0540 (10)	0.0389 (9)	0.0487 (9)	−0.0007 (8)	−0.0040 (8)	0.0017 (7)
C8	0.0548 (11)	0.0380 (9)	0.0460 (9)	0.0003 (7)	−0.0025 (8)	0.0015 (7)
C9	0.0594 (11)	0.0429 (10)	0.0454 (9)	0.0030 (8)	−0.0038 (8)	0.0003 (7)
C10	0.0696 (12)	0.0448 (10)	0.0430 (9)	0.0034 (9)	−0.0063 (8)	0.0032 (8)
C11	0.0725 (13)	0.0401 (10)	0.0518 (10)	−0.0040 (9)	−0.0083 (9)	0.0048 (8)
C12	0.0933 (16)	0.0515 (11)	0.0533 (11)	0.0069 (10)	−0.0063 (10)	−0.0058 (9)
C13	0.0605 (11)	0.0397 (9)	0.0425 (9)	0.0014 (8)	−0.0036 (8)	0.0000 (7)
C14	0.0619 (12)	0.0448 (10)	0.0618 (11)	−0.0033 (9)	−0.0036 (9)	0.0008 (8)
C15	0.0677 (13)	0.0550 (12)	0.0697 (13)	0.0111 (10)	−0.0122 (10)	−0.0024 (10)
C16	0.0933 (17)	0.0392 (11)	0.0660 (12)	0.0083 (10)	−0.0054 (11)	0.0028 (9)
C17	0.0812 (15)	0.0404 (10)	0.0696 (12)	−0.0061 (10)	0.0014 (11)	−0.0004 (9)
C18	0.0632 (12)	0.0445 (10)	0.0588 (11)	−0.0032 (9)	−0.0033 (9)	−0.0008 (8)
C19	0.0559 (11)	0.0503 (11)	0.0522 (10)	0.0020 (8)	−0.0043 (8)	0.0017 (8)
C20	0.136 (2)	0.0767 (16)	0.0541 (12)	−0.0326 (15)	0.0007 (13)	0.0039 (11)
C21	0.165 (3)	0.096 (2)	0.0536 (13)	−0.027 (2)	−0.0054 (15)	−0.0060 (13)
C22	0.0978 (18)	0.0840 (17)	0.0718 (16)	−0.0069 (14)	−0.0201 (13)	−0.0205 (13)
C23	0.0805 (16)	0.0777 (16)	0.0879 (17)	−0.0227 (13)	−0.0094 (13)	−0.0082 (13)
C24	0.0713 (14)	0.0710 (14)	0.0632 (12)	−0.0150 (11)	−0.0001 (10)	0.0004 (11)
C25	0.0588 (11)	0.0487 (10)	0.0483 (9)	−0.0006 (8)	0.0012 (8)	0.0039 (8)
C26	0.0548 (11)	0.0483 (10)	0.0605 (11)	0.0006 (8)	0.0019 (9)	−0.0014 (9)
C27	0.0543 (11)	0.0501 (11)	0.0557 (10)	0.0002 (8)	0.0000 (8)	0.0034 (8)
C28	0.0569 (12)	0.0542 (11)	0.0556 (10)	0.0029 (9)	−0.0049 (9)	0.0044 (9)
C29	0.0682 (13)	0.0526 (11)	0.0596 (11)	0.0076 (9)	−0.0064 (9)	−0.0045 (9)
C30	0.0751 (15)	0.0560 (13)	0.0912 (16)	−0.0024 (10)	−0.0197 (12)	−0.0040 (11)
C31	0.0543 (12)	0.0509 (12)	0.1012 (17)	0.0008 (9)	−0.0175 (11)	−0.0044 (12)
C32	0.0843 (17)	0.0668 (15)	0.131 (2)	−0.0035 (12)	−0.0251 (16)	0.0311 (15)
C33	0.105 (3)	0.083 (2)	0.263 (5)	−0.0263 (18)	−0.072 (3)	0.079 (3)
C34	0.096 (3)	0.0458 (19)	0.395 (8)	−0.0086 (17)	−0.079 (4)	0.031 (3)
C35	0.084 (2)	0.067 (2)	0.331 (7)	0.0177 (19)	−0.044 (3)	−0.062 (3)
C36	0.0637 (15)	0.0716 (16)	0.170 (3)	0.0132 (12)	−0.0193 (16)	−0.0429 (17)
N1	0.0728 (11)	0.0384 (8)	0.0437 (8)	−0.0004 (7)	−0.0091 (7)	0.0037 (6)
N2	0.0701 (11)	0.0454 (9)	0.0487 (8)	0.0024 (7)	−0.0149 (8)	0.0007 (7)
N3	0.0583 (11)	0.0499 (9)	0.0610 (10)	0.0037 (8)	−0.0101 (8)	0.0004 (7)
N4	0.0679 (11)	0.0538 (10)	0.0491 (9)	0.0028 (8)	−0.0096 (8)	0.0018 (7)
O1	0.0996 (11)	0.0519 (8)	0.0645 (8)	0.0159 (8)	−0.0274 (8)	−0.0014 (7)
O2	0.0886 (11)	0.0569 (9)	0.0785 (10)	0.0038 (7)	−0.0264 (8)	0.0104 (7)

Geometric parameters (Å, º) top

C1—C6	1.369 (3)	C19—C25	1.506 (2)
C1—C2	1.373 (3)	C20—C21	1.369 (3)
C1—C7	1.513 (2)	C20—H20	0.9300
C2—C3	1.379 (3)	C21—C22	1.355 (4)
C2—H2	0.9300	C21—H21	0.9300
C3—C4	1.349 (3)	C22—C23	1.350 (3)
C3—H3	0.9300	C22—H22	0.9300
C4—C5	1.364 (3)	C23—C24	1.369 (3)
C4—H4	0.9300	C23—H23	0.9300
C5—C6	1.381 (3)	C24—H24	0.9300
C5—H5	0.9300	C25—N3	1.459 (2)
C6—H6	0.9300	C25—C29	1.527 (3)
C7—N1	1.455 (2)	C25—H25	0.9800
C7—C11	1.535 (2)	C26—N3	1.465 (2)
C7—H7	0.9800	C26—C31	1.496 (3)
C8—N1	1.462 (2)	C26—C27	1.539 (3)
C8—C13	1.511 (2)	C26—H26	0.9800
C8—C9	1.539 (2)	C27—N4	1.469 (2)
C8—H8	0.9800	C27—C30	1.514 (3)
C9—N2	1.463 (2)	C27—H27	0.9800
C9—C12	1.511 (2)	C28—O2	1.234 (2)
C9—H9	0.9800	C28—N4	1.321 (2)
C10—O1	1.236 (2)	C28—C29	1.492 (3)
C10—N2	1.322 (2)	C29—H29A	0.9700
C10—C11	1.493 (2)	C29—H29B	0.9700
C11—H11A	0.9700	C30—H30A	0.9600
C11—H11B	0.9700	C30—H30B	0.9600
C12—H12A	0.9600	C30—H30C	0.9600
C12—H12B	0.9600	C31—C36	1.377 (3)
C12—H12C	0.9600	C31—C32	1.378 (4)
C13—C14	1.377 (3)	C32—C33	1.382 (4)
C13—C18	1.381 (2)	C32—H32	0.9300
C14—C15	1.385 (3)	C33—C34	1.373 (7)
C14—H14	0.9300	C33—H33	0.9300
C15—C16	1.369 (3)	C34—C35	1.363 (8)
C15—H15	0.9300	C34—H34	0.9300
C16—C17	1.365 (3)	C35—C36	1.366 (5)
C16—H16	0.9300	C35—H35	0.9300
C17—C18	1.376 (3)	C36—H36	0.9300
C17—H17	0.9300	N1—H1A	0.876 (19)
C18—H18	0.9300	N2—H2A	0.90 (2)
C19—C24	1.364 (3)	N3—H3A	0.87 (2)
C19—C20	1.372 (3)	N4—H4A	0.87 (2)

C6—C1—C2	117.44 (18)	C22—C21—C20	120.8 (2)
C6—C1—C7	123.39 (17)	C22—C21—H21	119.6
C2—C1—C7	119.14 (17)	C20—C21—H21	119.6
C1—C2—C3	121.5 (2)	C23—C22—C21	119.0 (2)
C1—C2—H2	119.2	C23—C22—H22	120.5
C3—C2—H2	119.2	C21—C22—H22	120.5
C4—C3—C2	120.2 (2)	C22—C23—C24	120.5 (2)
C4—C3—H3	119.9	C22—C23—H23	119.7
C2—C3—H3	119.9	C24—C23—H23	119.7
C3—C4—C5	119.4 (2)	C19—C24—C23	121.3 (2)
C3—C4—H4	120.3	C19—C24—H24	119.3
C5—C4—H4	120.3	C23—C24—H24	119.3
C4—C5—C6	120.5 (2)	N3—C25—C19	110.16 (14)
C4—C5—H5	119.8	N3—C25—C29	110.58 (16)
C6—C5—H5	119.8	C19—C25—C29	108.39 (15)
C1—C6—C5	120.9 (2)	N3—C25—H25	109.2
C1—C6—H6	119.5	C19—C25—H25	109.2
C5—C6—H6	119.5	C29—C25—H25	109.2
N1—C7—C1	110.20 (14)	N3—C26—C31	108.24 (16)
N1—C7—C11	111.32 (14)	N3—C26—C27	111.45 (15)
C1—C7—C11	108.75 (14)	C31—C26—C27	110.15 (15)
N1—C7—H7	108.8	N3—C26—H26	109.0
C1—C7—H7	108.8	C31—C26—H26	109.0
C11—C7—H7	108.8	C27—C26—H26	109.0
N1—C8—C13	107.78 (13)	N4—C27—C30	106.14 (15)
N1—C8—C9	111.05 (14)	N4—C27—C26	112.67 (15)
C13—C8—C9	112.28 (14)	C30—C27—C26	112.83 (16)
N1—C8—H8	108.5	N4—C27—H27	108.3
C13—C8—H8	108.5	C30—C27—H27	108.3
C9—C8—H8	108.5	C26—C27—H27	108.3
N2—C9—C12	106.57 (14)	O2—C28—N4	121.56 (17)
N2—C9—C8	111.11 (14)	O2—C28—C29	120.27 (18)
C12—C9—C8	113.98 (15)	N4—C28—C29	118.17 (17)
N2—C9—H9	108.3	C28—C29—C25	115.22 (16)
C12—C9—H9	108.3	C28—C29—H29A	108.5
C8—C9—H9	108.3	C25—C29—H29A	108.5
O1—C10—N2	121.76 (17)	C28—C29—H29B	108.5
O1—C10—C11	120.52 (16)	C25—C29—H29B	108.5
N2—C10—C11	117.72 (16)	H29A—C29—H29B	107.5
C10—C11—C7	114.13 (15)	C27—C30—H30A	109.5
C10—C11—H11A	108.7	C27—C30—H30B	109.5
C7—C11—H11A	108.7	H30A—C30—H30B	109.5
C10—C11—H11B	108.7	C27—C30—H30C	109.5
C7—C11—H11B	108.7	H30A—C30—H30C	109.5
H11A—C11—H11B	107.6	H30B—C30—H30C	109.5
C9—C12—H12A	109.5	C36—C31—C32	118.7 (2)
C9—C12—H12B	109.5	C36—C31—C26	120.3 (2)
H12A—C12—H12B	109.5	C32—C31—C26	120.9 (2)
C9—C12—H12C	109.5	C31—C32—C33	120.8 (4)
H12A—C12—H12C	109.5	C31—C32—H32	119.6
H12B—C12—H12C	109.5	C33—C32—H32	119.6
C14—C13—C18	118.40 (16)	C34—C33—C32	119.5 (5)
C14—C13—C8	121.63 (16)	C34—C33—H33	120.2
C18—C13—C8	119.96 (16)	C32—C33—H33	120.2
C13—C14—C15	120.50 (18)	C35—C34—C33	119.5 (4)
C13—C14—H14	119.8	C35—C34—H34	120.2
C15—C14—H14	119.8	C33—C34—H34	120.2
C16—C15—C14	120.38 (19)	C34—C35—C36	121.2 (5)
C16—C15—H15	119.8	C34—C35—H35	119.4
C14—C15—H15	119.8	C36—C35—H35	119.4
C17—C16—C15	119.41 (18)	C35—C36—C31	120.3 (4)
C17—C16—H16	120.3	C35—C36—H36	119.9
C15—C16—H16	120.3	C31—C36—H36	119.9
C16—C17—C18	120.56 (19)	C7—N1—C8	118.18 (14)
C16—C17—H17	119.7	C7—N1—H1A	107.0 (12)
C18—C17—H17	119.7	C8—N1—H1A	106.2 (12)
C17—C18—C13	120.75 (19)	C10—N2—C9	125.64 (16)
C17—C18—H18	119.6	C10—N2—H2A	117.7 (13)
C13—C18—H18	119.6	C9—N2—H2A	116.6 (13)
C24—C19—C20	117.58 (19)	C25—N3—C26	117.12 (15)
C24—C19—C25	121.33 (17)	C25—N3—H3A	107.6 (15)
C20—C19—C25	120.94 (18)	C26—N3—H3A	106.1 (15)
C21—C20—C19	120.7 (2)	C28—N4—C27	127.07 (16)
C21—C20—H20	119.6	C28—N4—H4A	117.6 (14)
C19—C20—H20	119.6	C27—N4—H4A	114.3 (14)

C6—C1—C2—C3	−1.7 (3)	C24—C19—C25—N3	−137.32 (19)
C7—C1—C2—C3	176.56 (19)	C20—C19—C25—N3	47.3 (3)
C1—C2—C3—C4	0.6 (4)	C24—C19—C25—C29	101.6 (2)
C2—C3—C4—C5	1.0 (4)	C20—C19—C25—C29	−73.8 (2)
C3—C4—C5—C6	−1.5 (4)	N3—C26—C27—N4	−75.63 (19)
C2—C1—C6—C5	1.2 (3)	C31—C26—C27—N4	164.21 (17)
C7—C1—C6—C5	−177.0 (2)	N3—C26—C27—C30	164.19 (16)
C4—C5—C6—C1	0.3 (4)	C31—C26—C27—C30	44.0 (2)
C6—C1—C7—N1	−14.8 (2)	O2—C28—C29—C25	119.9 (2)
C2—C1—C7—N1	167.09 (17)	N4—C28—C29—C25	−59.8 (2)
C6—C1—C7—C11	107.5 (2)	N3—C25—C29—C28	81.2 (2)
C2—C1—C7—C11	−70.6 (2)	C19—C25—C29—C28	−157.99 (16)
N1—C8—C9—N2	79.72 (18)	N3—C26—C31—C36	137.3 (2)
C13—C8—C9—N2	−159.53 (15)	C27—C26—C31—C36	−100.6 (2)
N1—C8—C9—C12	−159.86 (16)	N3—C26—C31—C32	−46.1 (3)
C13—C8—C9—C12	−39.1 (2)	C27—C26—C31—C32	75.9 (2)
O1—C10—C11—C7	−113.7 (2)	C36—C31—C32—C33	0.6 (4)
N2—C10—C11—C7	65.3 (2)	C26—C31—C32—C33	−176.0 (2)
N1—C7—C11—C10	−79.9 (2)	C31—C32—C33—C34	0.9 (5)
C1—C7—C11—C10	158.55 (16)	C32—C33—C34—C35	−2.1 (6)
N1—C8—C13—C14	40.2 (2)	C33—C34—C35—C36	1.9 (7)
C9—C8—C13—C14	−82.4 (2)	C34—C35—C36—C31	−0.4 (5)
N1—C8—C13—C18	−140.06 (17)	C32—C31—C36—C35	−0.9 (4)
C9—C8—C13—C18	97.33 (19)	C26—C31—C36—C35	175.7 (2)
C18—C13—C14—C15	−0.1 (3)	C1—C7—N1—C8	−173.45 (15)
C8—C13—C14—C15	179.61 (17)	C11—C7—N1—C8	65.8 (2)
C13—C14—C15—C16	0.5 (3)	C13—C8—N1—C7	169.15 (15)
C14—C15—C16—C17	−0.5 (3)	C9—C8—N1—C7	−67.5 (2)
C15—C16—C17—C18	0.3 (3)	O1—C10—N2—C9	−179.67 (18)
C16—C17—C18—C13	0.1 (3)	C11—C10—N2—C9	1.4 (3)
C14—C13—C18—C17	−0.1 (3)	C12—C9—N2—C10	168.85 (18)
C8—C13—C18—C17	−179.88 (17)	C8—C9—N2—C10	−66.4 (2)
C24—C19—C20—C21	0.0 (4)	C19—C25—N3—C26	169.44 (16)
C25—C19—C20—C21	175.5 (2)	C29—C25—N3—C26	−70.8 (2)
C19—C20—C21—C22	−1.3 (5)	C31—C26—N3—C25	−169.93 (17)
C20—C21—C22—C23	1.5 (5)	C27—C26—N3—C25	68.8 (2)
C21—C22—C23—C24	−0.4 (4)	O2—C28—N4—C27	174.06 (18)
C20—C19—C24—C23	1.2 (3)	C29—C28—N4—C27	−6.2 (3)
C25—C19—C24—C23	−174.4 (2)	C30—C27—N4—C28	−170.8 (2)
C22—C23—C24—C19	−1.0 (4)	C26—C27—N4—C28	65.3 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C6—H6···N1	0.93	2.45	2.797 (2)	102
N2—H2A···O2ⁱ	0.90 (2)	2.02 (2)	2.911 (2)	170.2 (18)
N4—H4A···O1ⁱ	0.87 (2)	2.03 (2)	2.884 (2)	167 (2)
N1—H1A···Cg1ⁱⁱ	0.88 (2)	2.93 (2)	3.707 (2)	149.5 (2)
C18—H18···Cg5ⁱⁱⁱ	0.93	2.95	3.872 (2)	171

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

Experimental details

Crystal data
Chemical formula	C₁₈H₂₀N₂O
M_r	280.36
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	295
a, b, c (Å)	10.8621 (3), 21.3210 (7), 13.3890 (4)
β (°)	91.167 (2)
V (Å³)	3100.13 (16)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.08
Crystal size (mm)	0.26 × 0.22 × 0.18

Data collection
Diffractometer	Bruker Kappa APEXII diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.981, 0.987
No. of measured, independent and observed [I > 2σ(I)] reflections	32883, 7003, 4175
R_int	0.034
(sin θ/λ)_max (Å⁻¹)	0.647

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.049, 0.150, 1.01
No. of reflections	7003
No. of parameters	397
No. of restraints	1
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.26, −0.18

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
C6—H6···N1	0.93	2.45	2.797 (2)	102
N2—H2A···O2ⁱ	0.90 (2)	2.02 (2)	2.911 (2)	170.2 (18)
N4—H4A···O1ⁱ	0.87 (2)	2.03 (2)	2.884 (2)	167 (2)
N1—H1A···Cg1ⁱⁱ	0.88 (2)	2.93 (2)	3.707 (2)	149.5 (2)
C18—H18···Cg5ⁱⁱⁱ	0.93	2.95	3.872 (2)	171

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

Acknowledgements

The authors wish to acknowledge SAIF, IIT, Madras for the data collection.

References

Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555–1573. CrossRef CAS Web of Science Google Scholar
Bruker (2004). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Gopalakrishnan, M., Sureshkumar, P., Thanusu, J., Kanagarajan, V., Govindaraju, R. & Jayasri, G. (2007). J. Enzyme Inhib. Med. Chem. 22, 709–715. Web of Science CrossRef PubMed CAS Google Scholar
Sheldrick, G. M. (1996). SADABS, University of Göttingen, Germany. 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
Thennarasu, S. & Perumal, P. T. (2002). Molecules, 7, 487–493. Web of Science CrossRef CAS Google Scholar
Wlodarczyk, N., Gilleron, P., Millet, R., Houssin, R., Goossens, J., Lemoine, A., Pommery, N., Wei, M. & He'nichart, J. (2006). Oncol. Res. 16, 107–118. CAS Google Scholar