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

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ISSN: 2056-9890

3-Hy­dr­oxy-4-phenyl-1-(prop-2-en-1-yl)-2,3,4,5-tetra­hydro-1H-1,5-benzodiazepin-2-one

aLaboratoire de Chimie Organique Hétérocyclique, Pôle de Compétences Pharmacochimie, Université Mohammed V-Agdal, BP 1014 Avenue Ibn Batout, Rabat, Morocco, bDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia, and cChemistry Department, King Abdulaziz University, PO Box 80203 Jeddah, Saudi Arabia
*Correspondence e-mail: seikweng@um.edu.my

(Received 17 December 2011; accepted 18 December 2011; online 23 December 2011)

The asymmetric unit of the title compound, C18H18N2O2, contains three independent mol­ecules. In each, the seven-membered diazepine ring adopts a boat conformation with the hy­droxy-substituted C atom at the prow and fused-ring C atoms at the stern. In the crystal, the mol­ecules are linked by O—H⋯O and N—H⋯O hydrogen bonds. The allyl group of one mol­ecule is equally disordered over two positions.

Related literature

For a related structure, see: Rida et al. (2011[Rida, M., Essassi, E. M., Massip, S., Lazar, S. & Zouihri, H. (2011). Acta Cryst. E67, o945-o946.]).

[Scheme 1]

Experimental

Crystal data
  • C18H18N2O2

  • Mr = 294.34

  • Monoclinic, C 2/c

  • a = 51.6665 (8) Å

  • b = 14.5766 (2) Å

  • c = 11.9316 (2) Å

  • β = 90.965 (2)°

  • V = 8984.7 (2) Å3

  • Z = 24

  • Mo Kα radiation

  • μ = 0.09 mm−1

  • T = 293 K

  • 0.21 × 0.15 × 0.13 mm

Data collection
  • Bruker APEX DUO diffractometer

  • 98635 measured reflections

  • 11182 independent reflections

  • 8815 reflections with I > 2σ(I)

  • Rint = 0.045

Refinement
  • R[F2 > 2σ(F2)] = 0.052

  • wR(F2) = 0.153

  • S = 1.01

  • 11182 reflections

  • 604 parameters

  • 16 restraints

  • H-atom parameters constrained

  • Δρmax = 0.72 e Å−3

  • Δρmin = −0.74 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
O1—H1o⋯O2i 0.84 1.96 2.786 (2) 167
O5—H5o⋯O6ii 0.84 2.30 3.022 (2) 145
N1—H1n⋯O3 0.88 2.58 3.142 (2) 123
N3—H3n⋯O4iii 0.88 2.40 2.900 (2) 116
Symmetry codes: (i) [-x+1, y, -z+{\script{1\over 2}}]; (ii) [-x+{\script{1\over 2}}, -y+{\script{3\over 2}}, -z+1]; (iii) [x, -y, z-{\script{1\over 2}}].

Data collection: APEX2 (Bruker, 2010[Bruker (2010). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2010[Bruker (2010). 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: X-SEED (Barbour, 2001[Barbour, L. J. (2001). J. Supramol. Chem. 1, 189-191.]); software used to prepare material for publication: publCIF (Westrip, 2010[Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.]).

Supporting information


Comment top

A previous study describes 3-hydroxy-4-phenyl-1-[(3-phenyl-4,5-dihydro-1,2-oxazol-5-yl)methyl]-4,5-dihydro-1H-1,5-benzodiazepine-2(3H)-one (Rida et al., 2011). The present study has an ally group in place of the 3-phenyl-4,5-dihyro-1,2-oxazol-5-yl group. The compound, C18H18N2O2 (Scheme I) crystallizes as three independent molecules, one of which has the allyl group disordered over two positions (Fig. 1). In these three molecules, the seven-membered diazepine ring adopts a boat conformation with the hydroxy-substituted C atom at the prow and fused-ring C atoms at the stern.

Despite the present of amino and hydroxy groups, the crystal structure features few hydrogen bonds (Table 1).

Related literature top

For a related structure, see: Rida et al. (2011).

Experimental top

To a solution of 3-hydroxy-4-phenyl-4,5-dihydro-1H-1,5-benzodiazepin-2(3H)-one (1 g, 3.5 mmol) in DMF (20 ml) were added allyl bromide (0.5 g. 4.2 mmol), potassium carbonate (1 g, 7.4 mmol) and a catalytic quantity of tetra-n-buthyl ammonium bromide. The mixture was stirred at room temperature for 24 hours. The solution was filtered and the solvent removed under reduced pressure. The residue was recrystallized from ethanol to afford the compound as colorless crystals.

Refinement top

H-atoms were placed in calculated positions (C–H 0.93–0.98 and N–H 0.88 Å) and were included in the refinement in the riding model approximation, with U(H) set to 1.2U(C,N).

The allyl group of one molecule is disordered over two positions; the CH2–CH and CC distances were tightly restrained to 1.50±0.005 and 1.40±0.005 Å. The temperature factors of the primed atom were set to those of the unprimed atom, and the anisotropic temperature factors were restrained to be nearly isotropic.

Omitted were (1 1 0), (4 0 0), (3 1 0) and (2 0 0).

Computing details top

Data collection: APEX2 (Bruker, 2010); cell refinement: SAINT (Bruker, 2010); data reduction: SAINT (Bruker, 2010); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: X-SEED (Barbour, 2001); software used to prepare material for publication: publCIF (Westrip, 2010).

Figures top
[Figure 1] Fig. 1. Thermal ellipsoid plot (Barbour, 2001) of the three independent molecules of C18H18N2O2 at the 50% probability level; hydrogen atoms are drawn as spheres of arbitrary radius. The disorder in one allyl group is not shown.
3-Hydroxy-4-phenyl-1-(prop-2-en-1-yl)-2,3,4,5-tetrahydro-1H- 1,5-benzodiazepin-2-one top
Crystal data top
C18H18N2O2F(000) = 3744
Mr = 294.34Dx = 1.306 Mg m3
Monoclinic, C2/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2ycCell parameters from 9776 reflections
a = 51.6665 (8) Åθ = 2.5–27.5°
b = 14.5766 (2) ŵ = 0.09 mm1
c = 11.9316 (2) ÅT = 293 K
β = 90.965 (2)°Prism, colorless
V = 8984.7 (2) Å30.21 × 0.15 × 0.13 mm
Z = 24
Data collection top
Bruker APEX DUO
diffractometer
8815 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.045
Graphite monochromatorθmax = 28.3°, θmin = 2.3°
ω scansh = 6868
98635 measured reflectionsk = 1919
11182 independent reflectionsl = 1515
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)] = 0.052Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.153H-atom parameters constrained
S = 1.01 w = 1/[σ2(Fo2) + (0.0786P)2 + 10.8059P]
where P = (Fo2 + 2Fc2)/3
11182 reflections(Δ/σ)max = 0.001
604 parametersΔρmax = 0.72 e Å3
16 restraintsΔρmin = 0.74 e Å3
Crystal data top
C18H18N2O2V = 8984.7 (2) Å3
Mr = 294.34Z = 24
Monoclinic, C2/cMo Kα radiation
a = 51.6665 (8) ŵ = 0.09 mm1
b = 14.5766 (2) ÅT = 293 K
c = 11.9316 (2) Å0.21 × 0.15 × 0.13 mm
β = 90.965 (2)°
Data collection top
Bruker APEX DUO
diffractometer
8815 reflections with I > 2σ(I)
98635 measured reflectionsRint = 0.045
11182 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.05216 restraints
wR(F2) = 0.153H-atom parameters constrained
S = 1.01 w = 1/[σ2(Fo2) + (0.0786P)2 + 10.8059P]
where P = (Fo2 + 2Fc2)/3
11182 reflectionsΔρmax = 0.72 e Å3
604 parametersΔρmin = 0.74 e Å3
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
O10.46395 (2)0.49919 (8)0.24790 (9)0.0258 (2)
H1O0.47680.48330.21040.039*
O20.49909 (2)0.42796 (8)0.39543 (9)0.0254 (2)
O30.42884 (3)0.12182 (9)0.12871 (12)0.0417 (3)
H3O0.42890.07570.17100.063*
O40.38520 (4)0.08749 (10)0.23349 (11)0.0558 (5)
O50.28615 (2)0.65848 (8)0.53439 (11)0.0317 (3)
H5O0.27540.69500.50540.048*
O60.23456 (2)0.65290 (8)0.52216 (10)0.0295 (3)
N10.44510 (3)0.26012 (9)0.31924 (11)0.0240 (3)
H1N0.44950.20410.29950.029*
N20.46785 (2)0.36338 (9)0.50005 (10)0.0199 (3)
N30.38017 (3)0.03270 (9)0.07443 (11)0.0245 (3)
H3N0.37380.02200.08950.029*
N40.35925 (3)0.14387 (11)0.09582 (13)0.0352 (4)
N50.26551 (3)0.42490 (10)0.45243 (11)0.0258 (3)
H5N0.25900.40130.39010.031*
N60.23191 (3)0.51238 (9)0.60356 (11)0.0227 (3)
C10.43185 (3)0.27309 (10)0.41930 (13)0.0215 (3)
C20.40848 (3)0.22715 (12)0.43807 (14)0.0280 (3)
H20.40140.19000.38200.034*
C30.39572 (3)0.23611 (13)0.53835 (15)0.0313 (4)
H30.38060.20310.55010.038*
C40.40526 (3)0.29392 (12)0.62158 (14)0.0289 (4)
H40.39620.30210.68750.035*
C50.42850 (3)0.33939 (11)0.60546 (13)0.0244 (3)
H50.43490.37900.66040.029*
C60.44231 (3)0.32611 (10)0.50729 (12)0.0203 (3)
C70.48666 (3)0.34345 (11)0.59069 (13)0.0238 (3)
H7A0.47770.34330.66140.029*
H7B0.49930.39250.59380.029*
C80.50061 (3)0.25390 (12)0.57856 (15)0.0310 (4)
H80.51160.23710.63740.037*
C90.49894 (4)0.19689 (13)0.49419 (19)0.0407 (4)
H9A0.48820.21040.43310.049*
H9B0.50850.14290.49520.049*
C100.47628 (3)0.40596 (10)0.40691 (12)0.0199 (3)
C110.45605 (3)0.42556 (10)0.31523 (12)0.0208 (3)
H110.43970.44190.35060.025*
C120.45194 (3)0.33759 (10)0.24566 (12)0.0209 (3)
H120.46850.32260.21150.025*
C130.43239 (3)0.35188 (11)0.15081 (13)0.0225 (3)
C140.44088 (3)0.35804 (13)0.04135 (14)0.0293 (4)
H140.45850.35600.02710.035*
C150.42323 (4)0.36731 (14)0.04743 (15)0.0356 (4)
H150.42910.37120.12050.043*
C160.39702 (4)0.37079 (13)0.02703 (16)0.0359 (4)
H160.38520.37610.08630.043*
C170.38845 (4)0.36631 (13)0.08187 (17)0.0350 (4)
H170.37080.36980.09590.042*
C180.40596 (3)0.35664 (12)0.17052 (15)0.0288 (3)
H180.40000.35330.24350.035*
C190.36579 (3)0.11140 (11)0.10302 (13)0.0231 (3)
C200.35985 (3)0.13185 (12)0.21494 (15)0.0292 (3)
H200.36710.09700.27150.035*
C210.34330 (4)0.20317 (14)0.24280 (19)0.0396 (4)
H210.33950.21590.31770.048*
C220.33236 (4)0.25554 (14)0.1593 (2)0.0464 (5)
H220.32100.30290.17800.056*
C230.33826 (3)0.23755 (13)0.0481 (2)0.0403 (5)
H230.33110.27350.00780.048*
C240.35487 (3)0.16635 (12)0.01918 (15)0.0282 (3)
C250.33697 (5)0.14175 (17)0.1726 (2)0.0595 (8)
H25A0.33490.08000.20140.071*0.50
H25B0.32130.15750.13090.071*0.50
H25C0.33950.09300.22700.071*0.50
H25D0.32130.12840.12980.071*0.50
C260.34037 (9)0.2076 (3)0.2700 (3)0.0361 (8)0.50
H260.35530.21060.31430.043*0.50
C270.31929 (9)0.2621 (3)0.2860 (4)0.0514 (9)0.50
H27A0.30480.25630.23920.062*0.50
H27B0.31940.30490.34370.062*0.50
C26'0.33372 (10)0.2330 (3)0.2343 (3)0.0361 (8)0.50
H26'0.33380.28800.19490.043*0.50
C27'0.33081 (10)0.2328 (3)0.3450 (3)0.0514 (9)0.50
H27C0.33080.17750.38400.062*0.50
H27D0.32880.28780.38330.062*0.50
C280.38237 (4)0.11630 (12)0.13676 (14)0.0336 (4)
C290.40592 (3)0.12239 (11)0.06246 (13)0.0272 (3)
H290.40510.17970.01960.033*
C300.40587 (3)0.04118 (11)0.01933 (13)0.0240 (3)
H300.40870.01450.02510.029*
C310.42762 (3)0.04703 (11)0.10277 (14)0.0246 (3)
C320.44697 (3)0.01911 (12)0.10342 (15)0.0293 (4)
H320.44720.06510.04940.035*
C330.46606 (3)0.01722 (13)0.18410 (17)0.0344 (4)
H330.47890.06180.18360.041*
C340.46599 (3)0.05065 (13)0.26528 (16)0.0327 (4)
H340.47860.05140.31980.039*
C350.44694 (3)0.11747 (13)0.26473 (16)0.0330 (4)
H350.44690.16350.31870.040*
C360.42802 (3)0.11597 (12)0.18396 (16)0.0310 (4)
H360.41540.16150.18380.037*
C370.26079 (3)0.38385 (11)0.55772 (13)0.0237 (3)
C380.27134 (4)0.29858 (12)0.58668 (16)0.0317 (4)
H380.28250.26930.53770.038*
C390.26540 (4)0.25737 (12)0.68735 (16)0.0364 (4)
H390.27240.20030.70530.044*
C400.24913 (4)0.30073 (13)0.76138 (16)0.0365 (4)
H400.24520.27300.82920.044*
C410.23863 (4)0.38550 (12)0.73449 (14)0.0299 (4)
H410.22790.41490.78490.036*
C420.24410 (3)0.42702 (11)0.63247 (13)0.0230 (3)
C430.20376 (3)0.52092 (12)0.61385 (15)0.0287 (3)
H43A0.19930.58550.61680.034*
H43B0.19860.49320.68400.034*
C440.18876 (3)0.47685 (12)0.51980 (17)0.0337 (4)
H440.17080.47510.52590.040*
C450.19871 (4)0.44052 (13)0.42947 (17)0.0370 (4)
H45A0.21650.44080.42000.044*
H45B0.18790.41450.37500.044*
C460.24510 (3)0.58222 (10)0.55556 (13)0.0222 (3)
C470.27447 (3)0.57209 (11)0.54834 (13)0.0234 (3)
H470.28100.54490.61840.028*
C480.28166 (3)0.50876 (11)0.45054 (13)0.0232 (3)
H480.27740.54150.38090.028*
C490.31030 (3)0.48644 (11)0.44854 (13)0.0240 (3)
C500.32412 (4)0.49960 (12)0.35145 (15)0.0320 (4)
H500.31590.52550.28910.038*
C510.35011 (4)0.47459 (14)0.34579 (18)0.0395 (4)
H510.35910.48410.28000.047*
C520.36235 (4)0.43598 (13)0.43717 (18)0.0385 (4)
H520.37970.41950.43360.046*
C530.34883 (4)0.42174 (15)0.53443 (17)0.0395 (4)
H530.35710.39550.59640.047*
C540.32298 (3)0.44652 (14)0.53984 (15)0.0331 (4)
H540.31400.43630.60560.040*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0316 (6)0.0209 (5)0.0252 (6)0.0022 (4)0.0077 (5)0.0063 (4)
O20.0235 (6)0.0288 (6)0.0242 (5)0.0039 (4)0.0041 (4)0.0014 (4)
O30.0538 (9)0.0302 (7)0.0402 (8)0.0015 (6)0.0232 (6)0.0012 (6)
O40.1104 (15)0.0351 (8)0.0220 (6)0.0117 (8)0.0094 (7)0.0045 (6)
O50.0259 (6)0.0239 (6)0.0454 (7)0.0047 (5)0.0033 (5)0.0001 (5)
O60.0302 (6)0.0221 (6)0.0363 (7)0.0039 (5)0.0036 (5)0.0023 (5)
N10.0324 (7)0.0171 (6)0.0226 (6)0.0012 (5)0.0008 (5)0.0016 (5)
N20.0211 (6)0.0202 (6)0.0183 (6)0.0008 (5)0.0009 (5)0.0002 (5)
N30.0273 (7)0.0195 (6)0.0269 (7)0.0042 (5)0.0016 (5)0.0043 (5)
N40.0412 (9)0.0357 (8)0.0292 (7)0.0154 (7)0.0185 (7)0.0130 (6)
N50.0273 (7)0.0282 (7)0.0218 (6)0.0036 (6)0.0010 (5)0.0066 (5)
N60.0213 (6)0.0214 (6)0.0256 (6)0.0008 (5)0.0032 (5)0.0004 (5)
C10.0247 (7)0.0180 (7)0.0218 (7)0.0008 (6)0.0001 (6)0.0026 (5)
C20.0277 (8)0.0257 (8)0.0305 (8)0.0044 (6)0.0040 (6)0.0031 (6)
C30.0226 (8)0.0330 (9)0.0385 (9)0.0043 (7)0.0021 (7)0.0104 (7)
C40.0250 (8)0.0350 (9)0.0268 (8)0.0035 (7)0.0057 (6)0.0082 (7)
C50.0258 (8)0.0262 (8)0.0214 (7)0.0022 (6)0.0021 (6)0.0026 (6)
C60.0221 (7)0.0180 (7)0.0208 (7)0.0004 (5)0.0018 (5)0.0031 (5)
C70.0252 (8)0.0258 (8)0.0204 (7)0.0011 (6)0.0014 (6)0.0000 (6)
C80.0286 (8)0.0298 (9)0.0343 (9)0.0037 (7)0.0043 (7)0.0055 (7)
C90.0427 (11)0.0267 (9)0.0526 (12)0.0100 (8)0.0050 (9)0.0047 (8)
C100.0242 (7)0.0155 (6)0.0200 (7)0.0008 (5)0.0037 (5)0.0032 (5)
C110.0239 (7)0.0193 (7)0.0195 (7)0.0018 (6)0.0042 (5)0.0018 (5)
C120.0224 (7)0.0218 (7)0.0187 (7)0.0015 (6)0.0017 (5)0.0004 (5)
C130.0244 (8)0.0213 (7)0.0217 (7)0.0008 (6)0.0006 (6)0.0004 (6)
C140.0268 (8)0.0375 (9)0.0236 (8)0.0023 (7)0.0008 (6)0.0022 (7)
C150.0439 (11)0.0387 (10)0.0241 (8)0.0025 (8)0.0052 (7)0.0033 (7)
C160.0407 (10)0.0309 (9)0.0355 (9)0.0048 (8)0.0162 (8)0.0007 (7)
C170.0256 (9)0.0347 (9)0.0447 (10)0.0058 (7)0.0062 (7)0.0030 (8)
C180.0266 (8)0.0314 (8)0.0287 (8)0.0043 (7)0.0018 (6)0.0009 (7)
C190.0199 (7)0.0219 (7)0.0278 (8)0.0045 (6)0.0044 (6)0.0018 (6)
C200.0263 (8)0.0319 (9)0.0296 (8)0.0050 (7)0.0009 (6)0.0005 (7)
C210.0321 (9)0.0353 (10)0.0509 (11)0.0080 (8)0.0137 (8)0.0086 (9)
C220.0273 (9)0.0282 (9)0.0833 (16)0.0007 (7)0.0142 (10)0.0039 (10)
C230.0212 (8)0.0330 (9)0.0668 (13)0.0017 (7)0.0031 (8)0.0188 (9)
C240.0222 (8)0.0266 (8)0.0360 (9)0.0068 (6)0.0081 (6)0.0084 (7)
C250.0658 (15)0.0596 (14)0.0545 (13)0.0373 (12)0.0432 (12)0.0344 (11)
C260.041 (2)0.045 (2)0.0226 (19)0.0109 (15)0.0109 (15)0.0086 (15)
C270.062 (2)0.0432 (19)0.049 (2)0.0150 (16)0.0163 (16)0.0183 (15)
C26'0.041 (2)0.045 (2)0.0226 (19)0.0109 (15)0.0109 (15)0.0086 (15)
C27'0.062 (2)0.0432 (19)0.049 (2)0.0150 (16)0.0163 (16)0.0183 (15)
C280.0585 (12)0.0208 (8)0.0216 (8)0.0099 (8)0.0070 (8)0.0029 (6)
C290.0382 (9)0.0199 (7)0.0232 (7)0.0017 (6)0.0059 (6)0.0009 (6)
C300.0299 (8)0.0183 (7)0.0238 (7)0.0013 (6)0.0004 (6)0.0018 (6)
C310.0254 (8)0.0205 (7)0.0276 (8)0.0027 (6)0.0023 (6)0.0010 (6)
C320.0286 (8)0.0229 (8)0.0362 (9)0.0001 (6)0.0038 (7)0.0068 (7)
C330.0243 (8)0.0293 (9)0.0496 (11)0.0049 (7)0.0006 (7)0.0041 (8)
C340.0221 (8)0.0348 (9)0.0414 (10)0.0017 (7)0.0042 (7)0.0024 (8)
C350.0282 (9)0.0318 (9)0.0391 (10)0.0006 (7)0.0023 (7)0.0118 (7)
C360.0266 (8)0.0272 (8)0.0392 (9)0.0048 (7)0.0029 (7)0.0088 (7)
C370.0232 (7)0.0227 (7)0.0253 (7)0.0018 (6)0.0011 (6)0.0028 (6)
C380.0313 (9)0.0254 (8)0.0383 (9)0.0040 (7)0.0041 (7)0.0069 (7)
C390.0453 (11)0.0216 (8)0.0420 (10)0.0039 (7)0.0111 (8)0.0011 (7)
C400.0526 (12)0.0275 (9)0.0294 (9)0.0046 (8)0.0043 (8)0.0058 (7)
C410.0370 (9)0.0271 (8)0.0255 (8)0.0036 (7)0.0022 (7)0.0010 (6)
C420.0237 (7)0.0206 (7)0.0246 (7)0.0012 (6)0.0011 (6)0.0003 (6)
C430.0223 (8)0.0298 (8)0.0342 (9)0.0025 (6)0.0081 (6)0.0003 (7)
C440.0204 (8)0.0296 (9)0.0512 (11)0.0005 (7)0.0018 (7)0.0015 (8)
C450.0311 (9)0.0359 (10)0.0436 (10)0.0020 (8)0.0097 (8)0.0043 (8)
C460.0253 (8)0.0203 (7)0.0211 (7)0.0001 (6)0.0022 (6)0.0033 (6)
C470.0240 (8)0.0209 (7)0.0254 (7)0.0018 (6)0.0013 (6)0.0013 (6)
C480.0232 (7)0.0258 (8)0.0206 (7)0.0009 (6)0.0010 (6)0.0002 (6)
C490.0236 (8)0.0239 (7)0.0247 (7)0.0004 (6)0.0029 (6)0.0038 (6)
C500.0355 (9)0.0309 (9)0.0298 (9)0.0008 (7)0.0079 (7)0.0028 (7)
C510.0363 (10)0.0356 (10)0.0473 (11)0.0014 (8)0.0195 (9)0.0003 (8)
C520.0232 (8)0.0343 (10)0.0583 (12)0.0015 (7)0.0067 (8)0.0105 (9)
C530.0317 (10)0.0470 (11)0.0398 (10)0.0112 (8)0.0041 (8)0.0043 (9)
C540.0284 (9)0.0464 (10)0.0246 (8)0.0064 (8)0.0028 (6)0.0019 (7)
Geometric parameters (Å, º) top
O1—C111.4053 (18)C22—H220.9300
O1—H1O0.8400C23—C241.386 (3)
O2—C101.2309 (19)C23—H230.9300
O3—C291.413 (2)C25—C261.515 (4)
O3—H3O0.8400C25—C26'1.531 (4)
O4—C281.235 (2)C25—H25A0.9700
O5—C471.4073 (19)C25—H25B0.9700
O5—H5O0.8400C25—H25C0.9700
O6—C461.229 (2)C25—H25D0.9700
N1—C11.399 (2)C26—C271.364 (4)
N1—C121.477 (2)C26—H260.9300
N1—H1N0.8800C27—H27A0.9300
N2—C101.3513 (19)C27—H27B0.9300
N2—C61.4311 (19)C26'—C27'1.332 (4)
N2—C71.4706 (19)C26'—H26'0.9300
N3—C191.406 (2)C27'—H27C0.9300
N3—C301.477 (2)C27'—H27D0.9300
N3—H3N0.8800C28—C291.520 (3)
N4—C281.345 (3)C29—C301.534 (2)
N4—C241.425 (2)C29—H290.9800
N4—C251.484 (2)C30—C311.516 (2)
N5—C371.416 (2)C30—H300.9800
N5—C481.481 (2)C31—C321.389 (2)
N5—H5N0.8800C31—C361.396 (2)
N6—C461.357 (2)C32—C331.390 (3)
N6—C421.434 (2)C32—H320.9300
N6—C431.467 (2)C33—C341.384 (3)
C1—C21.402 (2)C33—H330.9300
C1—C61.405 (2)C34—C351.385 (3)
C2—C31.382 (2)C34—H340.9300
C2—H20.9300C35—C361.385 (3)
C3—C41.387 (3)C35—H350.9300
C3—H30.9300C36—H360.9300
C4—C51.388 (2)C37—C381.398 (2)
C4—H40.9300C37—C421.400 (2)
C5—C61.395 (2)C38—C391.382 (3)
C5—H50.9300C38—H380.9300
C7—C81.499 (2)C39—C401.383 (3)
C7—H7A0.9700C39—H390.9300
C7—H7B0.9700C40—C411.385 (3)
C8—C91.307 (3)C40—H400.9300
C8—H80.9300C41—C421.393 (2)
C9—H9A0.9300C41—H410.9300
C9—H9B0.9300C43—C441.498 (3)
C10—C111.527 (2)C43—H43A0.9700
C11—C121.540 (2)C43—H43B0.9700
C11—H110.9800C44—C451.313 (3)
C12—C131.518 (2)C44—H440.9300
C12—H120.9800C45—H45A0.9300
C13—C141.388 (2)C45—H45B0.9300
C13—C181.392 (2)C46—C471.528 (2)
C14—C151.393 (2)C47—C481.538 (2)
C14—H140.9300C47—H470.9800
C15—C161.381 (3)C48—C491.516 (2)
C15—H150.9300C48—H480.9800
C16—C171.381 (3)C49—C541.390 (2)
C16—H160.9300C49—C501.384 (2)
C17—C181.387 (2)C50—C511.394 (3)
C17—H170.9300C50—H500.9300
C18—H180.9300C51—C521.372 (3)
C19—C201.397 (2)C51—H510.9300
C19—C241.407 (2)C52—C531.380 (3)
C20—C211.383 (3)C52—H520.9300
C20—H200.9300C53—C541.386 (3)
C21—C221.383 (3)C53—H530.9300
C21—H210.9300C54—H540.9300
C22—C231.382 (3)
C11—O1—H1O109.5N4—C25—H25D109.3
C29—O3—H3O109.5C26'—C25—H25D109.3
C47—O5—H5O109.5H25C—C25—H25D107.9
C1—N1—C12121.97 (12)C27—C26—C25113.2 (4)
C1—N1—H1N119.0C27—C26—H26123.4
C12—N1—H1N119.0C25—C26—H26123.4
C10—N2—C6122.30 (13)C26—C27—H27A120.0
C10—N2—C7118.52 (13)C26—C27—H27B120.0
C6—N2—C7118.62 (12)H27A—C27—H27B120.0
C19—N3—C30120.48 (13)C27'—C26'—C25119.3 (4)
C19—N3—H3N119.8C27'—C26'—H26'120.3
C30—N3—H3N119.8C25—C26'—H26'120.3
C28—N4—C24122.98 (14)C26'—C27'—H27C120.0
C28—N4—C25117.62 (19)C26'—C27'—H27D120.0
C24—N4—C25119.13 (19)H27C—C27'—H27D120.0
C37—N5—C48117.89 (13)O4—C28—N4122.12 (19)
C37—N5—H5N121.1O4—C28—C29118.8 (2)
C48—N5—H5N121.1N4—C28—C29119.06 (15)
C46—N6—C42122.04 (13)O3—C29—C28110.18 (14)
C46—N6—C43118.52 (13)O3—C29—C30110.10 (14)
C42—N6—C43119.05 (13)C28—C29—C30109.48 (14)
N1—C1—C2120.46 (14)O3—C29—H29109.0
N1—C1—C6121.63 (14)C28—C29—H29109.0
C2—C1—C6117.72 (14)C30—C29—H29109.0
C3—C2—C1121.18 (16)N3—C30—C31112.53 (13)
C3—C2—H2119.4N3—C30—C29109.85 (13)
C1—C2—H2119.4C31—C30—C29112.41 (13)
C2—C3—C4120.56 (16)N3—C30—H30107.2
C2—C3—H3119.7C31—C30—H30107.2
C4—C3—H3119.7C29—C30—H30107.2
C5—C4—C3119.28 (15)C32—C31—C36118.48 (16)
C5—C4—H4120.4C32—C31—C30120.41 (14)
C3—C4—H4120.4C36—C31—C30121.04 (15)
C4—C5—C6120.40 (16)C31—C32—C33120.61 (16)
C4—C5—H5119.8C31—C32—H32119.7
C6—C5—H5119.8C33—C32—H32119.7
C5—C6—C1120.53 (14)C34—C33—C32120.35 (16)
C5—C6—N2118.90 (14)C34—C33—H33119.8
C1—C6—N2120.50 (13)C32—C33—H33119.8
N2—C7—C8114.44 (13)C33—C34—C35119.52 (17)
N2—C7—H7A108.7C33—C34—H34120.2
C8—C7—H7A108.7C35—C34—H34120.2
N2—C7—H7B108.7C36—C35—C34120.17 (16)
C8—C7—H7B108.7C36—C35—H35119.9
H7A—C7—H7B107.6C34—C35—H35119.9
C9—C8—C7127.04 (16)C35—C36—C31120.86 (16)
C9—C8—H8116.5C35—C36—H36119.6
C7—C8—H8116.5C31—C36—H36119.6
C8—C9—H9A120.0C38—C37—C42118.93 (15)
C8—C9—H9B120.0C38—C37—N5121.51 (15)
H9A—C9—H9B120.0C42—C37—N5119.47 (14)
O2—C10—N2122.25 (14)C39—C38—C37120.66 (17)
O2—C10—C11121.09 (13)C39—C38—H38119.7
N2—C10—C11116.67 (13)C37—C38—H38119.7
O1—C11—C10110.52 (12)C38—C39—C40120.19 (17)
O1—C11—C12111.50 (12)C38—C39—H39119.9
C10—C11—C12108.47 (12)C40—C39—H39119.9
O1—C11—H11108.8C41—C40—C39119.99 (17)
C10—C11—H11108.8C41—C40—H40120.0
C12—C11—H11108.8C39—C40—H40120.0
N1—C12—C13112.64 (13)C40—C41—C42120.38 (17)
N1—C12—C11110.39 (12)C40—C41—H41119.8
C13—C12—C11111.80 (12)C42—C41—H41119.8
N1—C12—H12107.2C41—C42—C37119.84 (15)
C13—C12—H12107.2C41—C42—N6119.50 (15)
C11—C12—H12107.2C37—C42—N6120.62 (14)
C14—C13—C18118.85 (15)N6—C43—C44113.71 (14)
C14—C13—C12119.57 (14)N6—C43—H43A108.8
C18—C13—C12121.56 (14)C44—C43—H43A108.8
C13—C14—C15120.59 (16)N6—C43—H43B108.8
C13—C14—H14119.7C44—C43—H43B108.8
C15—C14—H14119.7H43A—C43—H43B107.7
C16—C15—C14120.07 (17)C45—C44—C43125.67 (16)
C16—C15—H15120.0C45—C44—H44117.2
C14—C15—H15120.0C43—C44—H44117.2
C15—C16—C17119.66 (16)C44—C45—H45A120.0
C15—C16—H16120.2C44—C45—H45B120.0
C17—C16—H16120.2H45A—C45—H45B120.0
C16—C17—C18120.46 (17)O6—C46—N6122.86 (15)
C16—C17—H17119.8O6—C46—C47119.87 (14)
C18—C17—H17119.8N6—C46—C47117.23 (13)
C17—C18—C13120.36 (16)O5—C47—C46110.38 (13)
C17—C18—H18119.8O5—C47—C48109.73 (13)
C13—C18—H18119.8C46—C47—C48110.70 (13)
C20—C19—N3120.85 (15)O5—C47—H47108.7
C20—C19—C24118.27 (16)C46—C47—H47108.7
N3—C19—C24120.58 (15)C48—C47—H47108.7
C21—C20—C19121.01 (18)N5—C48—C49111.95 (13)
C21—C20—H20119.5N5—C48—C47109.90 (12)
C19—C20—H20119.5C49—C48—C47112.91 (13)
C20—C21—C22120.01 (19)N5—C48—H48107.3
C20—C21—H21120.0C49—C48—H48107.3
C22—C21—H21120.0C47—C48—H48107.3
C23—C22—C21120.05 (18)C54—C49—C50118.10 (16)
C23—C22—H22120.0C54—C49—C48121.68 (14)
C21—C22—H22120.0C50—C49—C48120.06 (15)
C22—C23—C24120.43 (18)C49—C50—C51121.01 (18)
C22—C23—H23119.8C49—C50—H50119.5
C24—C23—H23119.8C51—C50—H50119.5
C23—C24—C19120.22 (18)C52—C51—C50120.03 (18)
C23—C24—N4119.95 (16)C52—C51—H51120.0
C19—C24—N4119.64 (16)C50—C51—H51120.0
N4—C25—C26112.3 (2)C51—C52—C53119.77 (17)
N4—C25—C26'111.8 (2)C51—C52—H52120.1
N4—C25—H25A109.1C53—C52—H52120.1
C26—C25—H25A109.1C52—C53—C54120.12 (18)
N4—C25—H25B109.1C52—C53—H53119.9
C26—C25—H25B109.1C54—C53—H53119.9
H25A—C25—H25B107.9C49—C54—C53120.97 (17)
N4—C25—H25C109.3C49—C54—H54119.5
C26'—C25—H25C109.3C53—C54—H54119.5
C12—N1—C1—C2123.84 (16)C25—N4—C28—O42.1 (3)
C12—N1—C1—C661.3 (2)C24—N4—C28—C299.3 (2)
N1—C1—C2—C3177.18 (15)C25—N4—C28—C29176.74 (15)
C6—C1—C2—C32.1 (2)O4—C28—C29—O319.3 (2)
C1—C2—C3—C42.6 (3)N4—C28—C29—O3159.57 (15)
C2—C3—C4—C53.2 (3)O4—C28—C29—C30101.92 (18)
C3—C4—C5—C60.9 (2)N4—C28—C29—C3079.21 (19)
C4—C5—C6—C15.7 (2)C19—N3—C30—C3189.64 (17)
C4—C5—C6—N2171.11 (14)C19—N3—C30—C2936.41 (19)
N1—C1—C6—C5178.82 (14)O3—C29—C30—N3170.34 (13)
C2—C1—C6—C56.2 (2)C28—C29—C30—N349.08 (17)
N1—C1—C6—N24.5 (2)O3—C29—C30—C3163.54 (18)
C2—C1—C6—N2170.56 (14)C28—C29—C30—C31175.20 (14)
C10—N2—C6—C5137.42 (15)N3—C30—C31—C32119.09 (17)
C7—N2—C6—C551.28 (19)C29—C30—C31—C32116.26 (17)
C10—N2—C6—C145.8 (2)N3—C30—C31—C3657.7 (2)
C7—N2—C6—C1125.49 (15)C29—C30—C31—C3666.9 (2)
C10—N2—C7—C887.20 (17)C36—C31—C32—C330.9 (3)
C6—N2—C7—C884.43 (17)C30—C31—C32—C33176.02 (16)
N2—C7—C8—C94.8 (3)C31—C32—C33—C340.2 (3)
C6—N2—C10—O2170.89 (14)C32—C33—C34—C350.8 (3)
C7—N2—C10—O20.4 (2)C33—C34—C35—C360.4 (3)
C6—N2—C10—C118.9 (2)C34—C35—C36—C310.6 (3)
C7—N2—C10—C11179.78 (12)C32—C31—C36—C351.3 (3)
O2—C10—C11—O124.25 (19)C30—C31—C36—C35175.59 (17)
N2—C10—C11—O1155.95 (13)C48—N5—C37—C38111.46 (17)
O2—C10—C11—C1298.27 (16)C48—N5—C37—C4271.98 (19)
N2—C10—C11—C1281.53 (15)C42—C37—C38—C390.1 (3)
C1—N1—C12—C1396.21 (16)N5—C37—C38—C39176.51 (16)
C1—N1—C12—C1129.55 (19)C37—C38—C39—C400.8 (3)
O1—C11—C12—N1176.81 (12)C38—C39—C40—C410.3 (3)
C10—C11—C12—N154.89 (16)C39—C40—C41—C420.8 (3)
O1—C11—C12—C1356.96 (17)C40—C41—C42—C371.5 (3)
C10—C11—C12—C13178.88 (12)C40—C41—C42—N6176.56 (16)
N1—C12—C13—C14128.67 (16)C38—C37—C42—C411.1 (2)
C11—C12—C13—C14106.34 (17)N5—C37—C42—C41177.70 (15)
N1—C12—C13—C1849.6 (2)C38—C37—C42—N6176.99 (15)
C11—C12—C13—C1875.35 (19)N5—C37—C42—N60.3 (2)
C18—C13—C14—C151.0 (3)C46—N6—C42—C41137.53 (16)
C12—C13—C14—C15177.31 (16)C43—N6—C42—C4149.8 (2)
C13—C14—C15—C160.2 (3)C46—N6—C42—C3744.4 (2)
C14—C15—C16—C170.9 (3)C43—N6—C42—C37128.29 (16)
C15—C16—C17—C181.2 (3)C46—N6—C43—C4495.05 (18)
C16—C17—C18—C130.4 (3)C42—N6—C43—C4477.92 (19)
C14—C13—C18—C170.7 (3)N6—C43—C44—C456.1 (3)
C12—C13—C18—C17177.58 (16)C42—N6—C46—O6174.05 (15)
C30—N3—C19—C20116.39 (17)C43—N6—C46—O61.3 (2)
C30—N3—C19—C2470.0 (2)C42—N6—C46—C478.5 (2)
N3—C19—C20—C21172.62 (16)C43—N6—C46—C47178.74 (13)
C24—C19—C20—C211.1 (2)O6—C46—C47—O518.0 (2)
C19—C20—C21—C220.0 (3)N6—C46—C47—O5159.56 (14)
C20—C21—C22—C231.0 (3)O6—C46—C47—C48103.73 (17)
C21—C22—C23—C240.9 (3)N6—C46—C47—C4878.75 (17)
C22—C23—C24—C190.3 (3)C37—N5—C48—C4985.17 (17)
C22—C23—C24—N4175.14 (17)C37—N5—C48—C4741.14 (18)
C20—C19—C24—C231.2 (2)O5—C47—C48—N5168.89 (13)
N3—C19—C24—C23172.53 (15)C46—C47—C48—N546.82 (17)
C20—C19—C24—N4176.14 (15)O5—C47—C48—C4965.34 (17)
N3—C19—C24—N42.4 (2)C46—C47—C48—C49172.59 (13)
C28—N4—C24—C23143.55 (17)N5—C48—C49—C5468.0 (2)
C25—N4—C24—C2342.6 (2)C47—C48—C49—C5456.6 (2)
C28—N4—C24—C1941.5 (2)N5—C48—C49—C50107.31 (17)
C25—N4—C24—C19132.32 (17)C47—C48—C49—C50128.03 (16)
C28—N4—C25—C2664.3 (3)C54—C49—C50—C510.8 (3)
C24—N4—C25—C26121.5 (3)C48—C49—C50—C51176.27 (16)
C28—N4—C25—C26'91.2 (3)C49—C50—C51—C520.2 (3)
C24—N4—C25—C26'94.7 (3)C50—C51—C52—C530.2 (3)
N4—C25—C26—C27130.7 (4)C51—C52—C53—C540.1 (3)
C26'—C25—C26—C2736.7 (6)C50—C49—C54—C530.9 (3)
N4—C25—C26'—C27'131.1 (4)C48—C49—C54—C53176.30 (17)
C26—C25—C26'—C27'34.9 (6)C52—C53—C54—C490.4 (3)
C24—N4—C28—O4171.86 (16)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1o···O2i0.841.962.786 (2)167
O5—H5o···O6ii0.842.303.022 (2)145
N1—H1n···O30.882.583.142 (2)123
N3—H3n···O4iii0.882.402.900 (2)116
Symmetry codes: (i) x+1, y, z+1/2; (ii) x+1/2, y+3/2, z+1; (iii) x, y, z1/2.

Experimental details

Crystal data
Chemical formulaC18H18N2O2
Mr294.34
Crystal system, space groupMonoclinic, C2/c
Temperature (K)293
a, b, c (Å)51.6665 (8), 14.5766 (2), 11.9316 (2)
β (°) 90.965 (2)
V3)8984.7 (2)
Z24
Radiation typeMo Kα
µ (mm1)0.09
Crystal size (mm)0.21 × 0.15 × 0.13
Data collection
DiffractometerBruker APEX DUO
diffractometer
Absorption correction
No. of measured, independent and
observed [I > 2σ(I)] reflections
98635, 11182, 8815
Rint0.045
(sin θ/λ)max1)0.668
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.052, 0.153, 1.01
No. of reflections11182
No. of parameters604
No. of restraints16
H-atom treatmentH-atom parameters constrained
w = 1/[σ2(Fo2) + (0.0786P)2 + 10.8059P]
where P = (Fo2 + 2Fc2)/3
Δρmax, Δρmin (e Å3)0.72, 0.74

Computer programs: APEX2 (Bruker, 2010), SAINT (Bruker, 2010), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), X-SEED (Barbour, 2001), publCIF (Westrip, 2010).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1o···O2i0.841.962.786 (2)167
O5—H5o···O6ii0.842.303.022 (2)145
N1—H1n···O30.882.583.142 (2)123
N3—H3n···O4iii0.882.402.900 (2)116
Symmetry codes: (i) x+1, y, z+1/2; (ii) x+1/2, y+3/2, z+1; (iii) x, y, z1/2.
 

Acknowledgements

We thank Université Mohammed V-Agdal and the University of Malaya for supporting this study.

References

First citationBarbour, L. J. (2001). J. Supramol. Chem. 1, 189–191.  CrossRef CAS
First citationBruker (2010). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
First citationRida, M., Essassi, E. M., Massip, S., Lazar, S. & Zouihri, H. (2011). Acta Cryst. E67, o945–o946.  Web of Science CSD CrossRef IUCr Journals
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals
First citationWestrip, S. P. (2010). J. Appl. Cryst. 43, 920–925.  Web of Science CrossRef CAS IUCr Journals

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