organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890

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

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[Gopalakrishnan, M., Sureshkumar, P., Thanusu, J., Kanagarajan, V., Govindaraju, R. & Jayasri, G. (2007). J. Enzyme Inhib. Med. Chem. 22, 709-715.]); Wlodarczyk et al. (2006[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.]). For the synthetic procedure, see: Thennarasu & Perumal (2002[Thennarasu, S. & Perumal, P. T. (2002). Molecules, 7, 487-493.]). For hydrogen-bond motifs, see: Bernstein et al. (1995[Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.]).

[Scheme 1]

Experimental

Crystal data
  • C18H20N2O

  • Mr = 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[Sheldrick, G. M. (1996). SADABS, University of Göttingen, Germany.]) Tmin = 0.981, Tmax = 0.987

  • 32883 measured reflections

  • 7003 independent reflections

  • 4175 reflections with I > 2σ(I)

  • Rint = 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

  • Δρmax = 0.26 e Å−3

  • Δρmin = −0.18 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA 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—H1ACg1ii 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[Bruker (2004). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2004[Bruker (2004). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]); software used to prepare material for publication: SHELXL97.

Supporting information


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.

Refinement top

The H atoms from the N—H groups were located in difference Fourier maps and their positions and isotropic displacement parameters were freely refined. All other H atoms were positioned geometrically and refined using riding model with C—H = 0.93 Å and Uiso(H) = 1.2Ueq(C) for aromatic C—H, C—H = 0.98 Å and Uiso(H) = 1.2Ueq(C) for methine C—H, C—H = 0.97 Å and Uiso(H) = 1.2Ueq(C) for methylene C—H and C—H = 0.96 Å and Uiso(H) = 1.5Ueq(C) for methyl. The components of the anisotropic displacement parameters in direction of the bond of C33 and C34 were restrained to be equal within an effective standard deviation of 0.001 using the DELU command in SHELXL97 (Sheldrick, 2008).

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
[Figure 1] 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.
[Figure 2] 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
C18H20N2OF(000) = 1200
Mr = 280.36Dx = 1.201 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 2786 reflections
a = 10.8621 (3) Åθ = 1.9–27.4°
b = 21.3210 (7) ŵ = 0.08 mm1
c = 13.3890 (4) ÅT = 295 K
β = 91.167 (2)°Block, colourless
V = 3100.13 (16) Å30.26 × 0.22 × 0.18 mm
Z = 8
Data collection top
Bruker Kappa APEXII
diffractometer
7003 independent reflections
Radiation source: fine-focus sealed tube4175 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.034
ω and ϕ scansθmax = 27.4°, θmin = 1.9°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 1413
Tmin = 0.981, Tmax = 0.987k = 2727
32883 measured reflectionsl = 1717
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.049Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.150H atoms treated by a mixture of independent and constrained refinement
S = 1.01 w = 1/[σ2(Fo2) + (0.0613P)2 + 0.757P]
where P = (Fo2 + 2Fc2)/3
7003 reflections(Δ/σ)max < 0.001
397 parametersΔρmax = 0.26 e Å3
1 restraintΔρmin = 0.18 e Å3
Crystal data top
C18H20N2OV = 3100.13 (16) Å3
Mr = 280.36Z = 8
Monoclinic, P21/cMo Kα radiation
a = 10.8621 (3) ŵ = 0.08 mm1
b = 21.3210 (7) ÅT = 295 K
c = 13.3890 (4) Å0.26 × 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)
Tmin = 0.981, Tmax = 0.987Rint = 0.034
32883 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0491 restraint
wR(F2) = 0.150H atoms treated by a mixture of independent and constrained refinement
S = 1.01Δρmax = 0.26 e Å3
7003 reflectionsΔρmin = 0.18 e Å3
397 parameters
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
C10.05795 (17)0.04801 (8)0.11713 (12)0.0485 (4)
C20.0143 (2)0.10676 (9)0.09516 (15)0.0678 (6)
H20.05930.12020.12450.081*
C30.0773 (3)0.14624 (10)0.03052 (16)0.0795 (7)
H30.04630.18600.01730.095*
C40.1837 (2)0.12746 (12)0.01365 (17)0.0785 (7)
H40.22690.15430.05650.094*
C50.2275 (2)0.06876 (13)0.00506 (18)0.0847 (7)
H50.29980.05520.02640.102*
C60.16502 (19)0.02932 (11)0.07031 (16)0.0687 (6)
H60.19610.01050.08260.082*
C70.01134 (17)0.00817 (8)0.19307 (12)0.0473 (4)
H70.09910.00870.17750.057*
C80.03251 (17)0.10337 (7)0.24911 (12)0.0463 (4)
H80.12060.10070.23510.056*
C90.01501 (17)0.09158 (8)0.36136 (12)0.0493 (4)
H90.07020.07820.37120.059*
C100.09125 (18)0.01783 (8)0.37215 (13)0.0526 (4)
C110.00555 (19)0.03663 (8)0.29722 (13)0.0549 (5)
H11A0.08530.02410.32160.066*
H11B0.00560.08200.29140.066*
C120.0399 (2)0.14835 (9)0.42625 (14)0.0662 (6)
H12A0.03410.13680.49530.099*
H12B0.01970.18040.41080.099*
H12C0.12100.16400.41390.099*
C130.01396 (17)0.16719 (8)0.21681 (12)0.0476 (4)
C140.13663 (18)0.17781 (9)0.19508 (14)0.0562 (5)
H140.19280.14510.19980.067*
C150.1770 (2)0.23685 (9)0.16622 (15)0.0643 (5)
H150.26010.24360.15220.077*
C160.0951 (2)0.28531 (9)0.15823 (15)0.0663 (6)
H160.12220.32480.13830.080*
C170.0266 (2)0.27512 (9)0.17977 (15)0.0637 (5)
H170.08250.30790.17470.076*
C180.06729 (18)0.21665 (8)0.20889 (14)0.0556 (5)
H180.15050.21040.22340.067*
C190.57859 (17)0.06524 (9)0.20328 (13)0.0528 (4)
C200.5541 (3)0.05228 (12)0.10529 (16)0.0890 (8)
H200.50760.01710.08960.107*
C210.5974 (3)0.09052 (13)0.03036 (18)0.1049 (9)
H210.58140.08060.03570.126*
C220.6634 (2)0.14265 (12)0.05125 (19)0.0848 (7)
H220.69100.16900.00010.102*
C230.6884 (2)0.15582 (11)0.14736 (19)0.0822 (7)
H230.73400.19140.16250.099*
C240.6472 (2)0.11726 (10)0.22268 (16)0.0685 (6)
H240.66640.12670.28840.082*
C250.52358 (17)0.02607 (8)0.28651 (13)0.0519 (4)
H250.56520.03590.34890.062*
C260.51055 (17)0.08491 (8)0.34472 (14)0.0545 (5)
H260.55510.07240.40440.065*
C270.37168 (17)0.08639 (8)0.36986 (14)0.0534 (4)
H270.32690.08730.30710.064*
C280.32986 (17)0.02759 (9)0.39725 (14)0.0557 (5)
C290.38718 (18)0.04257 (9)0.29788 (14)0.0602 (5)
H29A0.37750.08710.28550.072*
H29B0.34240.02030.24690.072*
C300.3340 (2)0.14317 (10)0.43108 (18)0.0744 (6)
H30A0.38450.14600.48890.112*
H30B0.34420.18040.39140.112*
H30C0.24920.13920.45180.112*
C310.55368 (18)0.14851 (10)0.31237 (19)0.0691 (6)
C320.5286 (2)0.17105 (11)0.2185 (2)0.0944 (8)
H320.48880.14540.17310.113*
C330.5619 (3)0.23130 (17)0.1909 (4)0.1510 (17)
H330.54560.24590.12710.181*
C340.6192 (4)0.26937 (18)0.2584 (6)0.180 (3)
H340.63950.31040.24130.216*
C350.6460 (3)0.24657 (18)0.3505 (5)0.161 (2)
H350.68700.27200.39540.193*
C360.6138 (2)0.18703 (12)0.3781 (3)0.1021 (10)
H360.63240.17240.44140.122*
N10.03260 (15)0.05628 (7)0.18881 (11)0.0518 (4)
N20.09714 (16)0.04195 (7)0.39814 (11)0.0550 (4)
N30.53901 (17)0.04046 (7)0.26410 (12)0.0566 (4)
N40.33046 (16)0.03138 (8)0.42746 (12)0.0571 (4)
O10.16394 (14)0.05709 (6)0.40701 (10)0.0724 (4)
O20.28387 (14)0.06962 (6)0.44918 (11)0.0751 (4)
H1A0.0273 (17)0.0686 (9)0.1266 (15)0.060 (6)*
H2A0.1588 (18)0.0538 (9)0.4403 (15)0.065 (6)*
H3A0.616 (2)0.0465 (10)0.2477 (16)0.077 (7)*
H4A0.291 (2)0.0403 (10)0.4827 (17)0.073 (7)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0583 (11)0.0441 (10)0.0432 (9)0.0040 (8)0.0021 (8)0.0013 (7)
C20.0880 (16)0.0517 (12)0.0632 (12)0.0099 (10)0.0133 (11)0.0067 (9)
C30.120 (2)0.0524 (13)0.0659 (13)0.0023 (13)0.0062 (13)0.0130 (10)
C40.0900 (17)0.0830 (17)0.0627 (13)0.0259 (14)0.0033 (12)0.0208 (12)
C50.0633 (14)0.111 (2)0.0794 (15)0.0023 (13)0.0112 (11)0.0298 (14)
C60.0635 (13)0.0708 (14)0.0713 (13)0.0067 (10)0.0083 (10)0.0169 (11)
C70.0540 (10)0.0389 (9)0.0487 (9)0.0007 (8)0.0040 (8)0.0017 (7)
C80.0548 (11)0.0380 (9)0.0460 (9)0.0003 (7)0.0025 (8)0.0015 (7)
C90.0594 (11)0.0429 (10)0.0454 (9)0.0030 (8)0.0038 (8)0.0003 (7)
C100.0696 (12)0.0448 (10)0.0430 (9)0.0034 (9)0.0063 (8)0.0032 (8)
C110.0725 (13)0.0401 (10)0.0518 (10)0.0040 (9)0.0083 (9)0.0048 (8)
C120.0933 (16)0.0515 (11)0.0533 (11)0.0069 (10)0.0063 (10)0.0058 (9)
C130.0605 (11)0.0397 (9)0.0425 (9)0.0014 (8)0.0036 (8)0.0000 (7)
C140.0619 (12)0.0448 (10)0.0618 (11)0.0033 (9)0.0036 (9)0.0008 (8)
C150.0677 (13)0.0550 (12)0.0697 (13)0.0111 (10)0.0122 (10)0.0024 (10)
C160.0933 (17)0.0392 (11)0.0660 (12)0.0083 (10)0.0054 (11)0.0028 (9)
C170.0812 (15)0.0404 (10)0.0696 (12)0.0061 (10)0.0014 (11)0.0004 (9)
C180.0632 (12)0.0445 (10)0.0588 (11)0.0032 (9)0.0033 (9)0.0008 (8)
C190.0559 (11)0.0503 (11)0.0522 (10)0.0020 (8)0.0043 (8)0.0017 (8)
C200.136 (2)0.0767 (16)0.0541 (12)0.0326 (15)0.0007 (13)0.0039 (11)
C210.165 (3)0.096 (2)0.0536 (13)0.027 (2)0.0054 (15)0.0060 (13)
C220.0978 (18)0.0840 (17)0.0718 (16)0.0069 (14)0.0201 (13)0.0205 (13)
C230.0805 (16)0.0777 (16)0.0879 (17)0.0227 (13)0.0094 (13)0.0082 (13)
C240.0713 (14)0.0710 (14)0.0632 (12)0.0150 (11)0.0001 (10)0.0004 (11)
C250.0588 (11)0.0487 (10)0.0483 (9)0.0006 (8)0.0012 (8)0.0039 (8)
C260.0548 (11)0.0483 (10)0.0605 (11)0.0006 (8)0.0019 (9)0.0014 (9)
C270.0543 (11)0.0501 (11)0.0557 (10)0.0002 (8)0.0000 (8)0.0034 (8)
C280.0569 (12)0.0542 (11)0.0556 (10)0.0029 (9)0.0049 (9)0.0044 (9)
C290.0682 (13)0.0526 (11)0.0596 (11)0.0076 (9)0.0064 (9)0.0045 (9)
C300.0751 (15)0.0560 (13)0.0912 (16)0.0024 (10)0.0197 (12)0.0040 (11)
C310.0543 (12)0.0509 (12)0.1012 (17)0.0008 (9)0.0175 (11)0.0044 (12)
C320.0843 (17)0.0668 (15)0.131 (2)0.0035 (12)0.0251 (16)0.0311 (15)
C330.105 (3)0.083 (2)0.263 (5)0.0263 (18)0.072 (3)0.079 (3)
C340.096 (3)0.0458 (19)0.395 (8)0.0086 (17)0.079 (4)0.031 (3)
C350.084 (2)0.067 (2)0.331 (7)0.0177 (19)0.044 (3)0.062 (3)
C360.0637 (15)0.0716 (16)0.170 (3)0.0132 (12)0.0193 (16)0.0429 (17)
N10.0728 (11)0.0384 (8)0.0437 (8)0.0004 (7)0.0091 (7)0.0037 (6)
N20.0701 (11)0.0454 (9)0.0487 (8)0.0024 (7)0.0149 (8)0.0007 (7)
N30.0583 (11)0.0499 (9)0.0610 (10)0.0037 (8)0.0101 (8)0.0004 (7)
N40.0679 (11)0.0538 (10)0.0491 (9)0.0028 (8)0.0096 (8)0.0018 (7)
O10.0996 (11)0.0519 (8)0.0645 (8)0.0159 (8)0.0274 (8)0.0014 (7)
O20.0886 (11)0.0569 (9)0.0785 (10)0.0038 (7)0.0264 (8)0.0104 (7)
Geometric parameters (Å, º) top
C1—C61.369 (3)C19—C251.506 (2)
C1—C21.373 (3)C20—C211.369 (3)
C1—C71.513 (2)C20—H200.9300
C2—C31.379 (3)C21—C221.355 (4)
C2—H20.9300C21—H210.9300
C3—C41.349 (3)C22—C231.350 (3)
C3—H30.9300C22—H220.9300
C4—C51.364 (3)C23—C241.369 (3)
C4—H40.9300C23—H230.9300
C5—C61.381 (3)C24—H240.9300
C5—H50.9300C25—N31.459 (2)
C6—H60.9300C25—C291.527 (3)
C7—N11.455 (2)C25—H250.9800
C7—C111.535 (2)C26—N31.465 (2)
C7—H70.9800C26—C311.496 (3)
C8—N11.462 (2)C26—C271.539 (3)
C8—C131.511 (2)C26—H260.9800
C8—C91.539 (2)C27—N41.469 (2)
C8—H80.9800C27—C301.514 (3)
C9—N21.463 (2)C27—H270.9800
C9—C121.511 (2)C28—O21.234 (2)
C9—H90.9800C28—N41.321 (2)
C10—O11.236 (2)C28—C291.492 (3)
C10—N21.322 (2)C29—H29A0.9700
C10—C111.493 (2)C29—H29B0.9700
C11—H11A0.9700C30—H30A0.9600
C11—H11B0.9700C30—H30B0.9600
C12—H12A0.9600C30—H30C0.9600
C12—H12B0.9600C31—C361.377 (3)
C12—H12C0.9600C31—C321.378 (4)
C13—C141.377 (3)C32—C331.382 (4)
C13—C181.381 (2)C32—H320.9300
C14—C151.385 (3)C33—C341.373 (7)
C14—H140.9300C33—H330.9300
C15—C161.369 (3)C34—C351.363 (8)
C15—H150.9300C34—H340.9300
C16—C171.365 (3)C35—C361.366 (5)
C16—H160.9300C35—H350.9300
C17—C181.376 (3)C36—H360.9300
C17—H170.9300N1—H1A0.876 (19)
C18—H180.9300N2—H2A0.90 (2)
C19—C241.364 (3)N3—H3A0.87 (2)
C19—C201.372 (3)N4—H4A0.87 (2)
C6—C1—C2117.44 (18)C22—C21—C20120.8 (2)
C6—C1—C7123.39 (17)C22—C21—H21119.6
C2—C1—C7119.14 (17)C20—C21—H21119.6
C1—C2—C3121.5 (2)C23—C22—C21119.0 (2)
C1—C2—H2119.2C23—C22—H22120.5
C3—C2—H2119.2C21—C22—H22120.5
C4—C3—C2120.2 (2)C22—C23—C24120.5 (2)
C4—C3—H3119.9C22—C23—H23119.7
C2—C3—H3119.9C24—C23—H23119.7
C3—C4—C5119.4 (2)C19—C24—C23121.3 (2)
C3—C4—H4120.3C19—C24—H24119.3
C5—C4—H4120.3C23—C24—H24119.3
C4—C5—C6120.5 (2)N3—C25—C19110.16 (14)
C4—C5—H5119.8N3—C25—C29110.58 (16)
C6—C5—H5119.8C19—C25—C29108.39 (15)
C1—C6—C5120.9 (2)N3—C25—H25109.2
C1—C6—H6119.5C19—C25—H25109.2
C5—C6—H6119.5C29—C25—H25109.2
N1—C7—C1110.20 (14)N3—C26—C31108.24 (16)
N1—C7—C11111.32 (14)N3—C26—C27111.45 (15)
C1—C7—C11108.75 (14)C31—C26—C27110.15 (15)
N1—C7—H7108.8N3—C26—H26109.0
C1—C7—H7108.8C31—C26—H26109.0
C11—C7—H7108.8C27—C26—H26109.0
N1—C8—C13107.78 (13)N4—C27—C30106.14 (15)
N1—C8—C9111.05 (14)N4—C27—C26112.67 (15)
C13—C8—C9112.28 (14)C30—C27—C26112.83 (16)
N1—C8—H8108.5N4—C27—H27108.3
C13—C8—H8108.5C30—C27—H27108.3
C9—C8—H8108.5C26—C27—H27108.3
N2—C9—C12106.57 (14)O2—C28—N4121.56 (17)
N2—C9—C8111.11 (14)O2—C28—C29120.27 (18)
C12—C9—C8113.98 (15)N4—C28—C29118.17 (17)
N2—C9—H9108.3C28—C29—C25115.22 (16)
C12—C9—H9108.3C28—C29—H29A108.5
C8—C9—H9108.3C25—C29—H29A108.5
O1—C10—N2121.76 (17)C28—C29—H29B108.5
O1—C10—C11120.52 (16)C25—C29—H29B108.5
N2—C10—C11117.72 (16)H29A—C29—H29B107.5
C10—C11—C7114.13 (15)C27—C30—H30A109.5
C10—C11—H11A108.7C27—C30—H30B109.5
C7—C11—H11A108.7H30A—C30—H30B109.5
C10—C11—H11B108.7C27—C30—H30C109.5
C7—C11—H11B108.7H30A—C30—H30C109.5
H11A—C11—H11B107.6H30B—C30—H30C109.5
C9—C12—H12A109.5C36—C31—C32118.7 (2)
C9—C12—H12B109.5C36—C31—C26120.3 (2)
H12A—C12—H12B109.5C32—C31—C26120.9 (2)
C9—C12—H12C109.5C31—C32—C33120.8 (4)
H12A—C12—H12C109.5C31—C32—H32119.6
H12B—C12—H12C109.5C33—C32—H32119.6
C14—C13—C18118.40 (16)C34—C33—C32119.5 (5)
C14—C13—C8121.63 (16)C34—C33—H33120.2
C18—C13—C8119.96 (16)C32—C33—H33120.2
C13—C14—C15120.50 (18)C35—C34—C33119.5 (4)
C13—C14—H14119.8C35—C34—H34120.2
C15—C14—H14119.8C33—C34—H34120.2
C16—C15—C14120.38 (19)C34—C35—C36121.2 (5)
C16—C15—H15119.8C34—C35—H35119.4
C14—C15—H15119.8C36—C35—H35119.4
C17—C16—C15119.41 (18)C35—C36—C31120.3 (4)
C17—C16—H16120.3C35—C36—H36119.9
C15—C16—H16120.3C31—C36—H36119.9
C16—C17—C18120.56 (19)C7—N1—C8118.18 (14)
C16—C17—H17119.7C7—N1—H1A107.0 (12)
C18—C17—H17119.7C8—N1—H1A106.2 (12)
C17—C18—C13120.75 (19)C10—N2—C9125.64 (16)
C17—C18—H18119.6C10—N2—H2A117.7 (13)
C13—C18—H18119.6C9—N2—H2A116.6 (13)
C24—C19—C20117.58 (19)C25—N3—C26117.12 (15)
C24—C19—C25121.33 (17)C25—N3—H3A107.6 (15)
C20—C19—C25120.94 (18)C26—N3—H3A106.1 (15)
C21—C20—C19120.7 (2)C28—N4—C27127.07 (16)
C21—C20—H20119.6C28—N4—H4A117.6 (14)
C19—C20—H20119.6C27—N4—H4A114.3 (14)
C6—C1—C2—C31.7 (3)C24—C19—C25—N3137.32 (19)
C7—C1—C2—C3176.56 (19)C20—C19—C25—N347.3 (3)
C1—C2—C3—C40.6 (4)C24—C19—C25—C29101.6 (2)
C2—C3—C4—C51.0 (4)C20—C19—C25—C2973.8 (2)
C3—C4—C5—C61.5 (4)N3—C26—C27—N475.63 (19)
C2—C1—C6—C51.2 (3)C31—C26—C27—N4164.21 (17)
C7—C1—C6—C5177.0 (2)N3—C26—C27—C30164.19 (16)
C4—C5—C6—C10.3 (4)C31—C26—C27—C3044.0 (2)
C6—C1—C7—N114.8 (2)O2—C28—C29—C25119.9 (2)
C2—C1—C7—N1167.09 (17)N4—C28—C29—C2559.8 (2)
C6—C1—C7—C11107.5 (2)N3—C25—C29—C2881.2 (2)
C2—C1—C7—C1170.6 (2)C19—C25—C29—C28157.99 (16)
N1—C8—C9—N279.72 (18)N3—C26—C31—C36137.3 (2)
C13—C8—C9—N2159.53 (15)C27—C26—C31—C36100.6 (2)
N1—C8—C9—C12159.86 (16)N3—C26—C31—C3246.1 (3)
C13—C8—C9—C1239.1 (2)C27—C26—C31—C3275.9 (2)
O1—C10—C11—C7113.7 (2)C36—C31—C32—C330.6 (4)
N2—C10—C11—C765.3 (2)C26—C31—C32—C33176.0 (2)
N1—C7—C11—C1079.9 (2)C31—C32—C33—C340.9 (5)
C1—C7—C11—C10158.55 (16)C32—C33—C34—C352.1 (6)
N1—C8—C13—C1440.2 (2)C33—C34—C35—C361.9 (7)
C9—C8—C13—C1482.4 (2)C34—C35—C36—C310.4 (5)
N1—C8—C13—C18140.06 (17)C32—C31—C36—C350.9 (4)
C9—C8—C13—C1897.33 (19)C26—C31—C36—C35175.7 (2)
C18—C13—C14—C150.1 (3)C1—C7—N1—C8173.45 (15)
C8—C13—C14—C15179.61 (17)C11—C7—N1—C865.8 (2)
C13—C14—C15—C160.5 (3)C13—C8—N1—C7169.15 (15)
C14—C15—C16—C170.5 (3)C9—C8—N1—C767.5 (2)
C15—C16—C17—C180.3 (3)O1—C10—N2—C9179.67 (18)
C16—C17—C18—C130.1 (3)C11—C10—N2—C91.4 (3)
C14—C13—C18—C170.1 (3)C12—C9—N2—C10168.85 (18)
C8—C13—C18—C17179.88 (17)C8—C9—N2—C1066.4 (2)
C24—C19—C20—C210.0 (4)C19—C25—N3—C26169.44 (16)
C25—C19—C20—C21175.5 (2)C29—C25—N3—C2670.8 (2)
C19—C20—C21—C221.3 (5)C31—C26—N3—C25169.93 (17)
C20—C21—C22—C231.5 (5)C27—C26—N3—C2568.8 (2)
C21—C22—C23—C240.4 (4)O2—C28—N4—C27174.06 (18)
C20—C19—C24—C231.2 (3)C29—C28—N4—C276.2 (3)
C25—C19—C24—C23174.4 (2)C30—C27—N4—C28170.8 (2)
C22—C23—C24—C191.0 (4)C26—C27—N4—C2865.3 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C6—H6···N10.932.452.797 (2)102
N2—H2A···O2i0.90 (2)2.02 (2)2.911 (2)170.2 (18)
N4—H4A···O1i0.87 (2)2.03 (2)2.884 (2)167 (2)
N1—H1A···Cg1ii0.88 (2)2.93 (2)3.707 (2)149.5 (2)
C18—H18···Cg5iii0.932.953.872 (2)171
Symmetry codes: (i) x, y, z+1; (ii) x, y, z; (iii) x+1, y, z.

Experimental details

Crystal data
Chemical formulaC18H20N2O
Mr280.36
Crystal system, space groupMonoclinic, P21/c
Temperature (K)295
a, b, c (Å)10.8621 (3), 21.3210 (7), 13.3890 (4)
β (°) 91.167 (2)
V3)3100.13 (16)
Z8
Radiation typeMo Kα
µ (mm1)0.08
Crystal size (mm)0.26 × 0.22 × 0.18
Data collection
DiffractometerBruker Kappa APEXII
diffractometer
Absorption correctionMulti-scan
(SADABS; Sheldrick, 1996)
Tmin, Tmax0.981, 0.987
No. of measured, independent and
observed [I > 2σ(I)] reflections
32883, 7003, 4175
Rint0.034
(sin θ/λ)max1)0.647
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.049, 0.150, 1.01
No. of reflections7003
No. of parameters397
No. of restraints1
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)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···AD—HH···AD···AD—H···A
C6—H6···N10.932.452.797 (2)102
N2—H2A···O2i0.90 (2)2.02 (2)2.911 (2)170.2 (18)
N4—H4A···O1i0.87 (2)2.03 (2)2.884 (2)167 (2)
N1—H1A···Cg1ii0.88 (2)2.93 (2)3.707 (2)149.5 (2)
C18—H18···Cg5iii0.932.953.872 (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

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First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
First citationSpek, A. L. (2009). Acta Cryst. D65, 148–155.  Web of Science CrossRef CAS IUCr Journals Google Scholar
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First citationWlodarczyk, 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

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