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

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890

4-Methyl-N-(2-phenyl­eth­yl)-2-propyl-1H-benzimidazole-6-carboxamide

aR&D Center for Pharmaceuticals, School of Chemical Engineering & the Environment, Beijing Institute of Technology, Beijing 100083, People's Republic of China, and bSINOPEC Research Institute of Petroleum Processing, Beijing 100083, People's Republic of China
*Correspondence e-mail: jims-wang@hotmail.com

(Received 14 June 2012; accepted 23 August 2012; online 1 September 2012)

There are two independent mol­ecules in the asymmetric unit of the title compound, C20H23N3O, in which the dihedral angles between the phenyl ring of the phenyl­ethyl­amino group and the benzimidazole system are 73.98 (15) and 15.93 (16)°. The crystal packing features N—H⋯O and N—H⋯N hydrogen bonds.

Related literature

For the background to the title compound and its derivatives, see Mahiuddin et al. (2007[Mahiuddin, A., David, C. B. & Naresh, K. (2007). Top. Heterocycl. Chem. 9, 87-118.]); Namrata et al. (2012[Namrata, S., Annamalai, P., Kavita, R., Preeti, A., Arsad, A. & Amit, K. T. (2012). Int. Curr. Pharm. J. 1, 119-127.]); Zhang et al. (2012[Zhang, J., Wang, J. L., Zhou, Z. Z., Li, Z. H., Xue, W. Z., Xu, D., Hao, L. P., Han, X. F., Fei, F., Liu, T. & Liang, A. H. (2012). Bioorg. Med. Chem. 20, 4208-4216.]); For hydrogen bonding, see: Desiraju (1995[Desiraju, G. R. (1995). Angew. Chem. Int. Ed. Engl.. 34, 2311-2327.]).

[Scheme 1]

Experimental

Crystal data
  • C20H23N3O

  • Mr = 321.41

  • Triclinic, [P \overline 1]

  • a = 10.2028 (7) Å

  • b = 11.9126 (9) Å

  • c = 17.0553 (17) Å

  • α = 101.563 (4)°

  • β = 99.110 (4)°

  • γ = 113.808 (2)°

  • V = 1790.6 (3) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 0.08 mm−1

  • T = 296 K

  • 0.41 × 0.30 × 0.20 mm

Data collection
  • Bruker APEXII CCD area-detector diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2007[Bruker (2007). APEX2, SADABS and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.670, Tmax = 0.746

  • 17517 measured reflections

  • 6081 independent reflections

  • 4250 reflections with I > 2σ(I)

  • Rint = 0.029

Refinement
  • R[F2 > 2σ(F2)] = 0.049

  • wR(F2) = 0.155

  • S = 1.08

  • 6081 reflections

  • 450 parameters

  • 46 restraints

  • H atoms treated by a mixture of independent and constrained refinement

  • Δρmax = 0.37 e Å−3

  • Δρmin = −0.30 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
N1—H1⋯O2i 0.88 1.91 2.744 (2) 157
N4—H4⋯N2ii 0.89 2.01 2.882 (3) 165
N5—H5⋯O1 0.88 2.06 2.849 (4) 148
N6—H6⋯N3iii 0.88 2.25 3.109 (2) 169
Symmetry codes: (i) x+1, y+1, z; (ii) -x, -y+1, -z; (iii) -x+1, -y+1, -z.

Data collection: APEX2 (Bruker 2007[Bruker (2007). APEX2, SADABS and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: APEX2 and SAINT (Bruker 2007[Bruker (2007). APEX2, SADABS 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: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]).

Supporting information


Comment top

Benzimidazole is an important scaffold with biological activities generally ultilized in antihypertensive drugs, proton pump inhibitors and antimicrobial agents, etc. (Mahiuddin et al., 2007.; Namrata et al., 2012). As a part of our study of 6-substituted carbamoyl benzimidazoles as a nonpeptidic angiotensin II AT1 receptor antagonist (Zhang et al., 2012), herein we report the synthesis and crystal structure of the title compound of this family. In the asymmetric unit of the title compound, there are two independent molecules with different dihedral angles between the phenyl ring of the phenylethylamino and the benzimidazole ring. In the O1(carbonyl)-containing molecule, the dihedral angle between the phenyl ring of the phenylethylamino and the benzimidazole ring is -1.8 (5) °, while the O2(carbonyl)-containing one has the value of -1.0 (5) ° (Fig. 1). Intermolecular N—H···O and N—H···N hydrogen-bonding (Desiraju, 1995) interactions (Table 1 and Fig. 2,3) are found to stabilize the whole packing structure of the title compound. As shown in Fig.2, each one O2-containing molecule is surrounded by four O1-containing ones through H-bonding interactions.

Related literature top

For the background to the title compound and its derivatives, see Mahiuddin et al. (2007); Namrata et al. (2012); Zhang et al. (2012); For hydrogen bonding, see: Desiraju (1995).

Experimental top

A suspension of 4-methyl-2-propyl-1H-benzimidazole-6-carboxylic acid (2.18 g, 10 mmol) in thionyl chloride (20 ml, 276 mmol) was refluxed for 2 h, and then the excess thionyl chloride was removed under reduced pressure to provide the crude acid chloride as an off-white solid. The crude product was used in the next step without further purification. To a stirred suspension of above acid chloride in 100 ml of dichloromethane at 293 K was added triethylamine (1.52 g, 15 mmol) dropwise, followed by a solution of phenylethylamine (10 mmol) in 10 ml of dichloromethane. The resulted mixture was stirred overnight and then was filtered, the filtrate was washed with brine and dried over anhydrous sodium sulphate, then was filtered and concentrated. The residue was purified by column chromatography (ethyl acetate–methanol, 4:1 v/v) to afford the title compound as a white solid, yield 72%, m.p. 425 ~ 427 K; Single crystals suitable for X-ray diffraction were prepared by slow evaporation of a solution of the title compound in ethanol at room temperature.

Refinement top

The completeness of the final refinement is less than 97 percent due to the deficient diffraction on high degree.All H atoms were discernible in the difference electron density maps.Nevertheless, the hydrogen atoms were placed into idealized positions and allowed to ride on their respective carrier atoms, with C—H = 0.93 for aryl, 0.96 Å and 0.97 Å for methyl and methylene H atoms, respectively. The N—H bonds were defined with constraint refinement at 0.88 Å. Uiso(H) = 1.2Ueq(C)aryl/methylene/methyl.

Structure description top

Benzimidazole is an important scaffold with biological activities generally ultilized in antihypertensive drugs, proton pump inhibitors and antimicrobial agents, etc. (Mahiuddin et al., 2007.; Namrata et al., 2012). As a part of our study of 6-substituted carbamoyl benzimidazoles as a nonpeptidic angiotensin II AT1 receptor antagonist (Zhang et al., 2012), herein we report the synthesis and crystal structure of the title compound of this family. In the asymmetric unit of the title compound, there are two independent molecules with different dihedral angles between the phenyl ring of the phenylethylamino and the benzimidazole ring. In the O1(carbonyl)-containing molecule, the dihedral angle between the phenyl ring of the phenylethylamino and the benzimidazole ring is -1.8 (5) °, while the O2(carbonyl)-containing one has the value of -1.0 (5) ° (Fig. 1). Intermolecular N—H···O and N—H···N hydrogen-bonding (Desiraju, 1995) interactions (Table 1 and Fig. 2,3) are found to stabilize the whole packing structure of the title compound. As shown in Fig.2, each one O2-containing molecule is surrounded by four O1-containing ones through H-bonding interactions.

For the background to the title compound and its derivatives, see Mahiuddin et al. (2007); Namrata et al. (2012); Zhang et al. (2012); For hydrogen bonding, see: Desiraju (1995).

Computing details top

Data collection: APEX2 (Bruker 2007); cell refinement: APEX2 and SAINT (Bruker 2007); data reduction: SAINT (Bruker 2007); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).

Figures top
[Figure 1] Fig. 1. The molecular structure of the title compound with displacement ellipsoids drawn at the 50% probability level. H atoms are presented as small spheres of the arbitrary radius.
[Figure 2] Fig. 2. The special show of the intermolecular H-bonding in the crystal structure.
[Figure 3] Fig. 3. The packing structure of the title compound, all hydrogen-bonding interactions are omitted for clarity.
4-Methyl-N-(2-phenylethyl)-2-propyl-1H-benzimidazole- 6-carboxamide top
Crystal data top
C20H23N3OZ = 4
Mr = 321.41F(000) = 688
Triclinic, P1Dx = 1.192 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 10.2028 (7) ÅCell parameters from 362 reflections
b = 11.9126 (9) Åθ = 2.0–25.0°
c = 17.0553 (17) ŵ = 0.08 mm1
α = 101.563 (4)°T = 296 K
β = 99.110 (4)°Block, colorless
γ = 113.808 (2)°0.41 × 0.30 × 0.20 mm
V = 1790.6 (3) Å3
Data collection top
Bruker APEXII CCD area-detector
diffractometer
6081 independent reflections
Radiation source: fine-focus sealed tube4250 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.029
ω scansθmax = 25.0°, θmin = 2.0°
Absorption correction: multi-scan
(SADABS; Bruker, 2007)
h = 1112
Tmin = 0.670, Tmax = 0.746k = 1413
17517 measured reflectionsl = 1720
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.049H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.155 w = 1/[σ2(Fo2) + (0.0753P)2 + 0.4342P] P = (Fo2 + 2Fc2)/3
S = 1.08(Δ/σ)max < 0.001
6081 reflectionsΔρmax = 0.37 e Å3
450 parametersΔρmin = 0.30 e Å3
46 restraintsExtinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0088 (17)
Crystal data top
C20H23N3Oγ = 113.808 (2)°
Mr = 321.41V = 1790.6 (3) Å3
Triclinic, P1Z = 4
a = 10.2028 (7) ÅMo Kα radiation
b = 11.9126 (9) ŵ = 0.08 mm1
c = 17.0553 (17) ÅT = 296 K
α = 101.563 (4)°0.41 × 0.30 × 0.20 mm
β = 99.110 (4)°
Data collection top
Bruker APEXII CCD area-detector
diffractometer
6081 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2007)
4250 reflections with I > 2σ(I)
Tmin = 0.670, Tmax = 0.746Rint = 0.029
17517 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.04946 restraints
wR(F2) = 0.155H atoms treated by a mixture of independent and constrained refinement
S = 1.08Δρmax = 0.37 e Å3
6081 reflectionsΔρmin = 0.30 e Å3
450 parameters
Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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
xyzUiso*/Ueq
H10.7674 (19)1.1106 (15)0.1249 (14)0.060 (7)*
H40.2645 (15)0.1827 (16)0.1485 (14)0.055 (7)*
H50.2616 (18)0.460 (2)0.2126 (15)0.069 (8)*
H60.7939 (19)0.598 (2)0.2321 (15)0.066 (8)*
C10.3195 (3)1.2092 (3)0.08894 (19)0.0728 (8)
H1A0.22391.19480.09740.109*
H1B0.31591.20260.03150.109*
H1C0.39271.29320.12270.109*
C20.3606 (3)1.1097 (3)0.1127 (2)0.0710 (8)
H2A0.36191.11570.17040.085*
H2B0.28481.02500.07930.085*
C30.5086 (3)1.1247 (2)0.10119 (15)0.0503 (6)
H3A0.50671.11940.04350.060*
H3B0.58361.20980.13450.060*
C40.5540 (2)1.02936 (19)0.12349 (13)0.0427 (5)
C50.7011 (2)0.93810 (19)0.14869 (13)0.0407 (5)
C60.8141 (2)0.9008 (2)0.15921 (14)0.0473 (5)
C70.7821 (2)0.7941 (2)0.18722 (14)0.0481 (5)
H7A0.85500.76660.19630.058*
C80.6452 (2)0.72490 (19)0.20267 (13)0.0416 (5)
C90.5340 (2)0.76211 (19)0.18845 (13)0.0426 (5)
H9A0.44200.71630.19720.051*
C100.5623 (2)0.86912 (19)0.16083 (13)0.0403 (5)
C110.9585 (3)0.9701 (3)0.1396 (2)0.0711 (8)
H11A1.02150.93010.15110.107*
H11B1.00681.05800.17310.107*
H11C0.93980.96640.08190.107*
C120.6116 (2)0.6129 (2)0.23587 (13)0.0437 (5)
C130.6911 (3)0.4712 (2)0.29015 (16)0.0601 (6)
H13A0.63380.38980.24720.072*
H13B0.63220.47680.32880.072*
C140.8298 (3)0.4735 (3)0.33495 (18)0.0699 (7)
H14A0.89000.55600.37650.084*
H14B0.88660.46250.29610.084*
C150.7950 (3)0.3686 (3)0.37630 (15)0.0579 (6)
C160.7603 (3)0.2458 (3)0.33270 (16)0.0689 (7)
H16A0.76440.22890.27770.083*
C170.7198 (4)0.1472 (3)0.3681 (2)0.0823 (9)
H17A0.69710.06490.33710.099*
C180.7128 (4)0.1698 (4)0.4486 (2)0.0923 (10)
H18A0.68300.10310.47250.111*
C190.7503 (5)0.2916 (4)0.4931 (2)0.1045 (12)
H19A0.74940.30840.54860.125*
C200.7896 (4)0.3905 (3)0.45784 (18)0.0886 (10)
H20A0.81270.47270.48920.106*
C210.2363 (7)0.0418 (5)0.3386 (3)0.187 (3)
H21A0.31170.04480.36500.281*
H21B0.18020.04660.28610.281*
H21C0.17110.06750.37340.281*
C220.3053 (4)0.1261 (3)0.32530 (19)0.0923 (10)
H22A0.37270.09810.29120.111*
H22B0.36370.11890.37840.111*
C230.1962 (3)0.2635 (2)0.28424 (14)0.0564 (6)
H23A0.12530.28840.31680.068*
H23B0.24940.31490.28630.068*
C240.1116 (2)0.2973 (2)0.19662 (13)0.0444 (5)
C250.0603 (2)0.38852 (19)0.08105 (12)0.0388 (5)
C260.0660 (2)0.30365 (19)0.06467 (12)0.0381 (5)
C270.0696 (2)0.28931 (19)0.01351 (13)0.0412 (5)
H27A0.15560.23260.02310.049*
C280.0598 (2)0.36249 (18)0.07695 (12)0.0382 (5)
C290.1881 (2)0.44721 (19)0.06003 (13)0.0421 (5)
H29A0.27430.49480.10340.050*
C300.1921 (2)0.46316 (19)0.01772 (13)0.0427 (5)
C310.3295 (3)0.5560 (2)0.03364 (15)0.0644 (7)
H31A0.40810.59780.01690.097*
H31B0.30930.61900.05320.097*
H31C0.35890.51050.07480.097*
C320.0549 (2)0.34704 (19)0.16112 (13)0.0420 (5)
C330.1868 (3)0.3983 (2)0.30617 (14)0.0545 (6)
H33A0.08830.36770.31500.065*
H33B0.24960.48120.34690.065*
C340.2479 (4)0.3063 (3)0.31926 (17)0.0765 (8)
H34A0.35000.34170.31580.092*
H34B0.19150.22670.27460.092*
C350.2442 (3)0.2766 (3)0.40085 (16)0.0652 (7)
C360.1137 (4)0.2081 (4)0.4166 (2)0.0960 (10)
H36A0.02520.18130.37680.115*
C370.1083 (6)0.1767 (4)0.4904 (3)0.1156 (13)
H37A0.01750.13010.50010.139*
C380.2369 (7)0.2147 (4)0.5481 (2)0.1115 (13)
H38A0.23460.19260.59740.134*
C390.3665 (6)0.2835 (4)0.5348 (2)0.1176 (14)
H39A0.45440.31020.57510.141*
C400.3712 (4)0.3158 (3)0.4614 (2)0.0939 (10)
H40A0.46260.36500.45320.113*
N10.6923 (2)1.03909 (17)0.12434 (11)0.0445 (4)
N20.47131 (19)0.92760 (16)0.14350 (11)0.0444 (4)
N30.02963 (19)0.38310 (16)0.16468 (10)0.0438 (4)
N40.1741 (2)0.24659 (17)0.13948 (11)0.0439 (4)
N50.1783 (2)0.41362 (19)0.22348 (11)0.0506 (5)
N60.7166 (2)0.57415 (18)0.25232 (12)0.0502 (5)
O10.49045 (17)0.55903 (16)0.25059 (10)0.0586 (4)
O20.06237 (17)0.27366 (15)0.17288 (9)0.0585 (5)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0683 (18)0.0739 (18)0.096 (2)0.0448 (15)0.0272 (16)0.0343 (16)
C20.0631 (18)0.0694 (17)0.103 (2)0.0387 (15)0.0372 (16)0.0397 (16)
C30.0488 (14)0.0447 (12)0.0580 (14)0.0199 (11)0.0156 (11)0.0174 (11)
C40.0361 (12)0.0379 (11)0.0478 (13)0.0112 (9)0.0117 (10)0.0109 (9)
C50.0345 (12)0.0382 (11)0.0448 (12)0.0116 (9)0.0126 (9)0.0114 (9)
C60.0345 (12)0.0491 (13)0.0573 (14)0.0158 (10)0.0168 (10)0.0163 (11)
C70.0363 (12)0.0501 (13)0.0616 (14)0.0206 (10)0.0155 (11)0.0195 (11)
C80.0350 (12)0.0423 (11)0.0434 (12)0.0142 (10)0.0108 (9)0.0108 (9)
C90.0323 (11)0.0403 (11)0.0486 (13)0.0102 (9)0.0121 (9)0.0115 (10)
C100.0314 (11)0.0398 (11)0.0444 (12)0.0126 (9)0.0100 (9)0.0091 (9)
C110.0452 (15)0.0715 (17)0.112 (2)0.0267 (13)0.0388 (15)0.0443 (16)
C120.0375 (13)0.0449 (12)0.0429 (12)0.0142 (10)0.0098 (10)0.0109 (10)
C130.0540 (16)0.0580 (15)0.0710 (17)0.0239 (12)0.0123 (13)0.0305 (13)
C140.0584 (17)0.0790 (18)0.0801 (19)0.0301 (15)0.0177 (14)0.0418 (15)
C150.0525 (15)0.0703 (17)0.0542 (15)0.0282 (13)0.0100 (12)0.0270 (13)
C160.0774 (19)0.0803 (19)0.0532 (16)0.0353 (16)0.0220 (14)0.0254 (14)
C170.094 (2)0.0694 (18)0.081 (2)0.0336 (17)0.0212 (18)0.0268 (16)
C180.106 (3)0.100 (3)0.093 (3)0.048 (2)0.037 (2)0.061 (2)
C190.160 (4)0.121 (3)0.061 (2)0.075 (3)0.044 (2)0.047 (2)
C200.132 (3)0.088 (2)0.0579 (18)0.060 (2)0.0217 (18)0.0249 (16)
C210.290 (8)0.157 (4)0.116 (4)0.163 (5)0.035 (4)0.024 (3)
C220.107 (3)0.084 (2)0.0583 (18)0.024 (2)0.0059 (17)0.0165 (16)
C230.0521 (15)0.0667 (16)0.0455 (14)0.0215 (13)0.0105 (11)0.0195 (12)
C240.0408 (13)0.0484 (12)0.0463 (13)0.0195 (11)0.0152 (10)0.0168 (10)
C250.0373 (12)0.0401 (11)0.0453 (12)0.0186 (10)0.0178 (10)0.0171 (9)
C260.0308 (11)0.0402 (11)0.0423 (12)0.0142 (9)0.0103 (9)0.0132 (9)
C270.0331 (12)0.0430 (11)0.0480 (13)0.0137 (10)0.0158 (10)0.0179 (10)
C280.0372 (12)0.0366 (10)0.0426 (12)0.0154 (9)0.0144 (10)0.0150 (9)
C290.0344 (12)0.0400 (11)0.0446 (12)0.0102 (9)0.0108 (9)0.0116 (9)
C300.0348 (12)0.0406 (11)0.0476 (13)0.0101 (10)0.0153 (10)0.0135 (10)
C310.0487 (15)0.0639 (15)0.0549 (15)0.0010 (12)0.0177 (12)0.0186 (12)
C320.0396 (13)0.0395 (11)0.0446 (12)0.0140 (10)0.0143 (10)0.0131 (10)
C330.0585 (15)0.0595 (14)0.0436 (13)0.0230 (12)0.0143 (11)0.0179 (11)
C340.098 (2)0.090 (2)0.0664 (17)0.0549 (18)0.0341 (16)0.0359 (15)
C350.082 (2)0.0677 (16)0.0573 (16)0.0396 (15)0.0214 (15)0.0258 (13)
C360.091 (2)0.123 (3)0.095 (2)0.051 (2)0.0331 (19)0.064 (2)
C370.133 (3)0.136 (3)0.118 (3)0.069 (3)0.068 (3)0.074 (3)
C380.171 (4)0.109 (3)0.068 (2)0.069 (3)0.039 (3)0.036 (2)
C390.132 (4)0.116 (3)0.068 (2)0.040 (3)0.014 (2)0.017 (2)
C400.090 (2)0.091 (2)0.077 (2)0.0233 (19)0.0057 (18)0.0263 (18)
N10.0353 (11)0.0393 (10)0.0570 (11)0.0118 (8)0.0165 (9)0.0175 (9)
N20.0345 (10)0.0428 (10)0.0552 (11)0.0156 (8)0.0128 (8)0.0159 (8)
N30.0399 (11)0.0485 (10)0.0434 (10)0.0167 (9)0.0154 (8)0.0178 (8)
N40.0312 (10)0.0492 (11)0.0459 (11)0.0112 (9)0.0117 (9)0.0168 (9)
N50.0405 (12)0.0593 (12)0.0432 (11)0.0121 (10)0.0124 (9)0.0186 (9)
N60.0462 (12)0.0554 (11)0.0574 (12)0.0239 (10)0.0200 (10)0.0267 (9)
O10.0395 (9)0.0636 (10)0.0750 (11)0.0172 (8)0.0192 (8)0.0349 (9)
O20.0475 (10)0.0584 (10)0.0510 (10)0.0025 (8)0.0183 (8)0.0197 (8)
Geometric parameters (Å, º) top
C1—C21.511 (4)C21—H21B0.9600
C1—H1A0.9600C21—H21C0.9600
C1—H1B0.9600C22—C231.494 (4)
C1—H1C0.9600C22—H22A0.9700
C2—C31.498 (3)C22—H22B0.9700
C2—H2A0.9700C23—C241.487 (3)
C2—H2B0.9700C23—H23A0.9700
C3—C41.481 (3)C23—H23B0.9700
C3—H3A0.9700C24—N31.326 (3)
C3—H3B0.9700C24—N41.357 (3)
C4—N21.315 (3)C25—C261.392 (3)
C4—N11.366 (3)C25—N31.394 (3)
C5—N11.380 (3)C25—C301.399 (3)
C5—C61.393 (3)C26—N41.381 (3)
C5—C101.395 (3)C26—C271.382 (3)
C6—C71.382 (3)C27—C281.383 (3)
C6—C111.500 (3)C27—H27A0.9300
C7—C81.406 (3)C28—C291.408 (3)
C7—H7A0.9300C28—C321.490 (3)
C8—C91.380 (3)C29—C301.381 (3)
C8—C121.488 (3)C29—H29A0.9300
C9—C101.385 (3)C30—C311.500 (3)
C9—H9A0.9300C31—H31A0.9600
C10—N21.397 (3)C31—H31B0.9600
C11—H11A0.9600C31—H31C0.9600
C11—H11B0.9600C32—O21.240 (2)
C11—H11C0.9600C32—N51.333 (3)
C12—O11.235 (2)C33—N51.451 (3)
C12—N61.340 (3)C33—C341.499 (4)
C13—N61.449 (3)C33—H33A0.9700
C13—C141.486 (3)C33—H33B0.9700
C13—H13A0.9700C34—C351.505 (4)
C13—H13B0.9700C34—H34A0.9700
C14—C151.503 (3)C34—H34B0.9700
C14—H14A0.9700C35—C361.355 (4)
C14—H14B0.9700C35—C401.363 (4)
C15—C161.371 (4)C36—C371.386 (5)
C15—C201.377 (4)C36—H36A0.9300
C16—C171.373 (4)C37—C381.352 (6)
C16—H16A0.9300C37—H37A0.9300
C17—C181.364 (4)C38—C391.329 (6)
C17—H17A0.9300C38—H38A0.9300
C18—C191.359 (5)C39—C401.385 (5)
C18—H18A0.9300C39—H39A0.9300
C19—C201.375 (4)C40—H40A0.9300
C19—H19A0.9300N1—H10.883 (10)
C20—H20A0.9300N4—H40.892 (10)
C21—C221.444 (6)N5—H50.879 (10)
C21—H21A0.9600N6—H60.875 (10)
C2—C1—H1A109.5C21—C22—H22A108.9
C2—C1—H1B109.5C23—C22—H22A108.9
H1A—C1—H1B109.5C21—C22—H22B108.9
C2—C1—H1C109.5C23—C22—H22B108.9
H1A—C1—H1C109.5H22A—C22—H22B107.7
H1B—C1—H1C109.5C24—C23—C22117.0 (2)
C3—C2—C1113.1 (2)C24—C23—H23A108.0
C3—C2—H2A109.0C22—C23—H23A108.0
C1—C2—H2A109.0C24—C23—H23B108.0
C3—C2—H2B109.0C22—C23—H23B108.0
C1—C2—H2B109.0H23A—C23—H23B107.3
H2A—C2—H2B107.8N3—C24—N4112.61 (19)
C4—C3—C2115.24 (19)N3—C24—C23124.40 (19)
C4—C3—H3A108.5N4—C24—C23122.9 (2)
C2—C3—H3A108.5C26—C25—N3109.70 (18)
C4—C3—H3B108.5C26—C25—C30120.55 (18)
C2—C3—H3B108.5N3—C25—C30129.74 (18)
H3A—C3—H3B107.5N4—C26—C27131.64 (18)
N2—C4—N1112.09 (19)N4—C26—C25105.57 (17)
N2—C4—C3126.25 (19)C27—C26—C25122.78 (19)
N1—C4—C3121.65 (19)C26—C27—C28117.46 (18)
N1—C5—C6132.18 (19)C26—C27—H27A121.3
N1—C5—C10105.01 (18)C28—C27—H27A121.3
C6—C5—C10122.79 (19)C27—C28—C29119.67 (19)
C7—C6—C5115.18 (19)C27—C28—C32117.12 (18)
C7—C6—C11122.6 (2)C29—C28—C32123.21 (19)
C5—C6—C11122.2 (2)C30—C29—C28123.3 (2)
C6—C7—C8123.4 (2)C30—C29—H29A118.4
C6—C7—H7A118.3C28—C29—H29A118.4
C8—C7—H7A118.3C29—C30—C25116.26 (18)
C9—C8—C7119.63 (19)C29—C30—C31122.2 (2)
C9—C8—C12116.51 (19)C25—C30—C31121.58 (19)
C7—C8—C12123.85 (19)C30—C31—H31A109.5
C8—C9—C10118.61 (19)C30—C31—H31B109.5
C8—C9—H9A120.7H31A—C31—H31B109.5
C10—C9—H9A120.7C30—C31—H31C109.5
C9—C10—C5120.31 (19)H31A—C31—H31C109.5
C9—C10—N2129.93 (19)H31B—C31—H31C109.5
C5—C10—N2109.74 (18)O2—C32—N5120.66 (19)
C6—C11—H11A109.5O2—C32—C28120.42 (19)
C6—C11—H11B109.5N5—C32—C28118.92 (18)
H11A—C11—H11B109.5N5—C33—C34112.4 (2)
C6—C11—H11C109.5N5—C33—H33A109.1
H11A—C11—H11C109.5C34—C33—H33A109.1
H11B—C11—H11C109.5N5—C33—H33B109.1
O1—C12—N6120.5 (2)C34—C33—H33B109.1
O1—C12—C8120.5 (2)H33A—C33—H33B107.9
N6—C12—C8119.02 (19)C33—C34—C35114.4 (2)
N6—C13—C14113.7 (2)C33—C34—H34A108.7
N6—C13—H13A108.8C35—C34—H34A108.7
C14—C13—H13A108.8C33—C34—H34B108.7
N6—C13—H13B108.8C35—C34—H34B108.7
C14—C13—H13B108.8H34A—C34—H34B107.6
H13A—C13—H13B107.7C36—C35—C40117.3 (3)
C13—C14—C15110.8 (2)C36—C35—C34121.0 (3)
C13—C14—H14A109.5C40—C35—C34121.7 (3)
C15—C14—H14A109.5C35—C36—C37121.8 (4)
C13—C14—H14B109.5C35—C36—H36A119.1
C15—C14—H14B109.5C37—C36—H36A119.1
H14A—C14—H14B108.1C38—C37—C36119.2 (4)
C16—C15—C20117.6 (2)C38—C37—H37A120.4
C16—C15—C14120.9 (2)C36—C37—H37A120.4
C20—C15—C14121.5 (3)C39—C38—C37120.2 (4)
C15—C16—C17121.7 (3)C39—C38—H38A119.9
C15—C16—H16A119.1C37—C38—H38A119.9
C17—C16—H16A119.1C38—C39—C40120.4 (4)
C18—C17—C16120.1 (3)C38—C39—H39A119.8
C18—C17—H17A119.9C40—C39—H39A119.8
C16—C17—H17A119.9C35—C40—C39121.1 (4)
C19—C18—C17118.7 (3)C35—C40—H40A119.5
C19—C18—H18A120.6C39—C40—H40A119.5
C17—C18—H18A120.6C4—N1—C5107.75 (17)
C18—C19—C20121.4 (3)C4—N1—H1122.7 (16)
C18—C19—H19A119.3C5—N1—H1126.8 (16)
C20—C19—H19A119.3C4—N2—C10105.38 (17)
C19—C20—C15120.4 (3)C24—N3—C25104.92 (16)
C19—C20—H20A119.8C24—N4—C26107.21 (17)
C15—C20—H20A119.8C24—N4—H4127.3 (15)
C22—C21—H21A109.5C26—N4—H4125.2 (15)
C22—C21—H21B109.5C32—N5—C33122.83 (19)
H21A—C21—H21B109.5C32—N5—H5118.8 (17)
C22—C21—H21C109.5C33—N5—H5117.7 (17)
H21A—C21—H21C109.5C12—N6—C13120.33 (19)
H21B—C21—H21C109.5C12—N6—H6121.9 (17)
C21—C22—C23113.4 (4)C13—N6—H6116.7 (17)
C1—C2—C3—C4179.9 (2)C27—C28—C29—C300.8 (3)
C2—C3—C4—N27.6 (3)C32—C28—C29—C30178.92 (19)
C2—C3—C4—N1173.1 (2)C28—C29—C30—C250.7 (3)
N1—C5—C6—C7178.2 (2)C28—C29—C30—C31178.8 (2)
C10—C5—C6—C73.5 (3)C26—C25—C30—C290.1 (3)
N1—C5—C6—C113.2 (4)N3—C25—C30—C29179.91 (19)
C10—C5—C6—C11175.1 (2)C26—C25—C30—C31179.6 (2)
C5—C6—C7—C81.3 (3)N3—C25—C30—C310.4 (3)
C11—C6—C7—C8177.3 (2)C27—C28—C32—O21.8 (3)
C6—C7—C8—C91.1 (3)C29—C28—C32—O2177.9 (2)
C6—C7—C8—C12177.6 (2)C27—C28—C32—N5178.43 (19)
C7—C8—C9—C101.4 (3)C29—C28—C32—N51.9 (3)
C12—C8—C9—C10177.36 (18)N5—C33—C34—C35173.9 (2)
C8—C9—C10—C50.7 (3)C33—C34—C35—C3668.7 (4)
C8—C9—C10—N2178.6 (2)C33—C34—C35—C40112.2 (3)
N1—C5—C10—C9177.99 (18)C40—C35—C36—C371.1 (5)
C6—C5—C10—C93.3 (3)C34—C35—C36—C37178.1 (3)
N1—C5—C10—N20.3 (2)C35—C36—C37—C380.4 (6)
C6—C5—C10—N2178.35 (19)C36—C37—C38—C391.4 (7)
C9—C8—C12—O11.1 (3)C37—C38—C39—C400.7 (7)
C7—C8—C12—O1177.6 (2)C36—C35—C40—C391.7 (5)
C9—C8—C12—N6178.74 (19)C34—C35—C40—C39177.5 (3)
C7—C8—C12—N60.0 (3)C38—C39—C40—C350.9 (6)
N6—C13—C14—C15177.0 (2)N2—C4—N1—C51.6 (2)
C13—C14—C15—C1682.9 (3)C3—C4—N1—C5179.02 (19)
C13—C14—C15—C2093.9 (3)C6—C5—N1—C4179.2 (2)
C20—C15—C16—C170.8 (4)C10—C5—N1—C40.7 (2)
C14—C15—C16—C17176.1 (3)N1—C4—N2—C101.8 (2)
C15—C16—C17—C180.1 (5)C3—C4—N2—C10178.9 (2)
C16—C17—C18—C191.7 (5)C9—C10—N2—C4176.8 (2)
C17—C18—C19—C202.3 (6)C5—C10—N2—C41.3 (2)
C18—C19—C20—C151.4 (6)N4—C24—N3—C250.2 (2)
C16—C15—C20—C190.1 (5)C23—C24—N3—C25177.0 (2)
C14—C15—C20—C19176.8 (3)C26—C25—N3—C240.2 (2)
C21—C22—C23—C2467.5 (4)C30—C25—N3—C24179.8 (2)
C22—C23—C24—N3142.9 (3)N3—C24—N4—C260.2 (2)
C22—C23—C24—N440.1 (3)C23—C24—N4—C26177.1 (2)
N3—C25—C26—N40.1 (2)C27—C26—N4—C24179.0 (2)
C30—C25—C26—N4179.95 (18)C25—C26—N4—C240.1 (2)
N3—C25—C26—C27179.21 (18)O2—C32—N5—C334.5 (3)
C30—C25—C26—C270.8 (3)C28—C32—N5—C33175.66 (19)
N4—C26—C27—C28179.6 (2)C34—C33—N5—C3295.4 (3)
C25—C26—C27—C280.7 (3)O1—C12—N6—C132.0 (3)
C26—C27—C28—C290.1 (3)C8—C12—N6—C13175.6 (2)
C26—C27—C28—C32179.64 (17)C14—C13—N6—C12156.5 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1···O2i0.881.912.744 (2)157
N4—H4···N2ii0.892.012.882 (3)165
N5—H5···O10.882.062.849 (4)148
N6—H6···N3iii0.882.253.109 (2)169
Symmetry codes: (i) x+1, y+1, z; (ii) x, y+1, z; (iii) x+1, y+1, z.

Experimental details

Crystal data
Chemical formulaC20H23N3O
Mr321.41
Crystal system, space groupTriclinic, P1
Temperature (K)296
a, b, c (Å)10.2028 (7), 11.9126 (9), 17.0553 (17)
α, β, γ (°)101.563 (4), 99.110 (4), 113.808 (2)
V3)1790.6 (3)
Z4
Radiation typeMo Kα
µ (mm1)0.08
Crystal size (mm)0.41 × 0.30 × 0.20
Data collection
DiffractometerBruker APEXII CCD area-detector
Absorption correctionMulti-scan
(SADABS; Bruker, 2007)
Tmin, Tmax0.670, 0.746
No. of measured, independent and
observed [I > 2σ(I)] reflections
17517, 6081, 4250
Rint0.029
(sin θ/λ)max1)0.595
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.049, 0.155, 1.08
No. of reflections6081
No. of parameters450
No. of restraints46
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)0.37, 0.30

Computer programs: APEX2 (Bruker 2007), APEX2 and SAINT (Bruker 2007), SAINT (Bruker 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1···O2i0.8841.912.744 (2)156.70
N4—H4···N2ii0.8922.012.882 (3)164.50
N5—H5···O10.8792.062.849 (4)148.37
N6—H6···N3iii0.8752.253.109 (2)168.50
Symmetry codes: (i) x+1, y+1, z; (ii) x, y+1, z; (iii) x+1, y+1, z.
 

Acknowledgements

This work was supported by the National Technological Project for the Manufacture and Innovation of Key New Drugs (2009ZX09103-143).

References

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First citationDesiraju, G. R. (1995). Angew. Chem. Int. Ed. Engl.. 34, 2311–2327.  CrossRef CAS Web of Science Google Scholar
First citationMahiuddin, A., David, C. B. & Naresh, K. (2007). Top. Heterocycl. Chem. 9, 87–118.  Google Scholar
First citationNamrata, S., Annamalai, P., Kavita, R., Preeti, A., Arsad, A. & Amit, K. T. (2012). Int. Curr. Pharm. J. 1, 119–127.  Google Scholar
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
First citationZhang, J., Wang, J. L., Zhou, Z. Z., Li, Z. H., Xue, W. Z., Xu, D., Hao, L. P., Han, X. F., Fei, F., Liu, T. & Liang, A. H. (2012). Bioorg. Med. Chem. 20, 4208–4216.  Web of Science CrossRef CAS PubMed Google Scholar

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