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Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890

Napropamide

aDepartment of Chemistry and Research Institute of Natural Sciences, Gyeongsang National University, Jinju 660-701, Republic of Korea
*Correspondence e-mail: jekim@gnu.ac.kr, thkim@gnu.ac.kr

(Received 27 June 2013; accepted 29 June 2013; online 6 July 2013)

The title compound [systematic name: N,N-diethyl-2-(naphthalen-1-yl­oxy)propanamide], C17H21NO2, crystallizes with two independent mol­ecules in the asymmetric unit in which the dihedral angles between the naphthalene ring systems and the amide groups are 88.1 (9) and 88.7 (3)°. Four C—H⋯O hydrogen bonds stabilize the crystal structure.

Related literature

For the herbicidal effects of the title compound, see: Freeman (1986[Freeman, J. A. (1986). Can. J. Plant Sci. 66, 141-152.]). For information on the synthesis of the title compound, see: Gless (1986[Gless, R. D. Jr (1986). Synth. Commun. 16, 633-638.]). For a related crystal structure, see: Au-Yeung et al. (2009[Au-Yeung, H. Y., Pengo, P., Pantos, G. D., Otto, S. & Sanders, J. K. (2009). Chem. Commun. pp. 419-421.]).

[Scheme 1]

Experimental

Crystal data
  • C17H21NO2

  • Mr = 271.35

  • Monoclinic, P 21

  • a = 9.8733 (3) Å

  • b = 10.7710 (4) Å

  • c = 14.1044 (5) Å

  • β = 97.943 (2)°

  • V = 1485.55 (9) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 0.08 mm−1

  • T = 173 K

  • 0.35 × 0.18 × 0.15 mm

Data collection
  • Bruker APEXII CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2009[Bruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.973, Tmax = 0.988

  • 26573 measured reflections

  • 3897 independent reflections

  • 3297 reflections with I > 2σ(I)

  • Rint = 0.041

Refinement
  • R[F2 > 2σ(F2)] = 0.037

  • wR(F2) = 0.083

  • S = 1.03

  • 3897 reflections

  • 367 parameters

  • 1 restraint

  • H-atom parameters constrained

  • Δρmax = 0.15 e Å−3

  • Δρmin = −0.16 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
C25—H25⋯O2 0.95 2.41 3.228 (3) 144
C6—H6⋯O2i 0.95 2.53 3.388 (3) 150
C7—H7⋯O4ii 0.95 2.60 3.481 (3) 154
C23—H23⋯O4iii 0.95 2.46 3.376 (3) 161
Symmetry codes: (i) [-x+2, y-{\script{1\over 2}}, -z]; (ii) [-x+1, y-{\script{3\over 2}}, -z]; (iii) [-x+1, y-{\script{1\over 2}}, -z+1].

Data collection: APEX2 (Bruker, 2009[Bruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2009[Bruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Supporting information


Comment top

Napropamide (systematic name: N, N-diethyl-2-(1-naphthalenyloxy) propanamide) is a residual herbicide of the amide series. It is used as a control method for broadleaf grasses and annual grasses (Freeman, 1986). However its crystal structure has not yet been reported.

In the title compound (Scheme 1, Fig. 1), crystallizes with two independent molecules (Molecule A and Molecule B) in the asymmetric unit. The dihedral angles between the naphthalene ring systems and the amide groups are 88.1 (9) and 88.7 (3)° for Molecule A and Molecule B, respectively. C11 and C28 are chiral centres. All bond lengths and bond angles are normal and comparable to those observed in a similar crystal structure (Au-Yeung et al., 2009). In the crystal structure (Fig. 2), four C—H···O hydrogen bonds are observed (Table 1). These intermolecular interactions may contribute to the stabilization of the packing.

Related literature top

For the herbicidal effects of the title compound, see: Freeman (1986). For information on the synthesis of the title compound, see: Gless (1986). For a related crystal structure, see: Au-Yeung et al. (2009).

Experimental top

The title compound was purchased from the Dr. Ehrenstorfer GmbH Company. Slow evaporation of a solution in CH2Cl2 gave single crystals suitable for X-ray analysis.

Refinement top

All H-atoms were positioned geometrically and refined using a riding model with d(C—H) = 0.95 Å, Uiso = 1.2Ueq(C) for aromatic C—H, d(C—H) =1.00 Å, Uiso = 1.2Ueq(C) for chiral C—H, d(C—H) = 0.99 Å, Uiso = 1.2Ueq(C) for CH2 groups and d(C—H) = 0.98 Å, Uiso = 1.5Ueq(C) for CH3 groups. In the absence of significant anomalous scattering effects, Friedel pairs were merged.

Computing details top

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

Figures top
[Figure 1] Fig. 1. The asymmetric unit of the title compound with the atom numbering scheme. Displacement ellipsoids are drawn at the 50% probability level. Hydrogen atoms are represented by small spheres of arbitrary radius.
[Figure 2] Fig. 2. Crystal packing viewed along the a axis. The intermolecular C—H···O hydrogen bonds are shown as dashed lines.
N,N-diethyl-2-(naphthalen-1-yloxy)propanamide top
Crystal data top
C17H21NO2F(000) = 584
Mr = 271.35Dx = 1.213 Mg m3
Monoclinic, P21Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ybCell parameters from 9958 reflections
a = 9.8733 (3) Åθ = 2.4–28.2°
b = 10.7710 (4) ŵ = 0.08 mm1
c = 14.1044 (5) ÅT = 173 K
β = 97.943 (2)°Block, colourless
V = 1485.55 (9) Å30.35 × 0.18 × 0.15 mm
Z = 4
Data collection top
Bruker APEXII CCD
diffractometer
3897 independent reflections
Radiation source: fine-focus sealed tube3297 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.041
ϕ and ω scansθmax = 28.3°, θmin = 1.5°
Absorption correction: multi-scan
(SADABS; Bruker, 2009)
h = 1313
Tmin = 0.973, Tmax = 0.988k = 1214
26573 measured reflectionsl = 1818
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)] = 0.037Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.083H-atom parameters constrained
S = 1.03 w = 1/[σ2(Fo2) + (0.0333P)2 + 0.2525P]
where P = (Fo2 + 2Fc2)/3
3897 reflections(Δ/σ)max < 0.001
367 parametersΔρmax = 0.15 e Å3
1 restraintΔρmin = 0.16 e Å3
Crystal data top
C17H21NO2V = 1485.55 (9) Å3
Mr = 271.35Z = 4
Monoclinic, P21Mo Kα radiation
a = 9.8733 (3) ŵ = 0.08 mm1
b = 10.7710 (4) ÅT = 173 K
c = 14.1044 (5) Å0.35 × 0.18 × 0.15 mm
β = 97.943 (2)°
Data collection top
Bruker APEXII CCD
diffractometer
3897 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2009)
3297 reflections with I > 2σ(I)
Tmin = 0.973, Tmax = 0.988Rint = 0.041
26573 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0371 restraint
wR(F2) = 0.083H-atom parameters constrained
S = 1.03Δρmax = 0.15 e Å3
3897 reflectionsΔρmin = 0.16 e Å3
367 parameters
Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
O10.64959 (13)0.16746 (14)0.03108 (9)0.0340 (3)
O20.66356 (17)0.40562 (16)0.14147 (11)0.0447 (4)
O30.33269 (15)0.94175 (15)0.27007 (9)0.0365 (4)
O40.10307 (16)1.13370 (15)0.37266 (11)0.0410 (4)
N10.67648 (18)0.20374 (17)0.18196 (11)0.0343 (4)
N20.07201 (18)0.92770 (17)0.35334 (11)0.0328 (4)
C10.78359 (19)0.1750 (2)0.04740 (12)0.0285 (4)
C20.8753 (2)0.2628 (2)0.00987 (13)0.0335 (5)
H20.84710.32820.02820.040*
C31.0125 (2)0.2560 (2)0.02794 (13)0.0373 (5)
H31.07640.31690.00150.045*
C41.0541 (2)0.1635 (2)0.08256 (14)0.0369 (5)
H41.14710.15930.09270.044*
C50.9607 (2)0.0737 (2)0.12436 (13)0.0297 (4)
C60.9996 (2)0.0220 (2)0.18405 (14)0.0365 (5)
H61.09210.02770.19520.044*
C70.9068 (2)0.1059 (2)0.22572 (15)0.0398 (5)
H70.93480.16900.26590.048*
C80.7705 (2)0.0996 (2)0.20960 (15)0.0386 (5)
H80.70640.15840.23910.046*
C90.7284 (2)0.0093 (2)0.15167 (13)0.0323 (4)
H90.63550.00620.14120.039*
C100.8220 (2)0.0790 (2)0.10762 (12)0.0273 (4)
C110.5932 (2)0.2710 (2)0.01310 (14)0.0361 (5)
H110.61130.34690.02410.043*
C120.4395 (2)0.2515 (3)0.00062 (16)0.0500 (7)
H12A0.40390.24980.06780.075*
H12B0.39630.31960.03150.075*
H12C0.41890.17250.03000.075*
C130.6490 (2)0.2955 (2)0.11836 (14)0.0337 (5)
C140.6488 (2)0.0708 (2)0.16476 (16)0.0409 (5)
H14A0.59020.06070.10240.049*
H14B0.59760.03840.21510.049*
C150.7780 (3)0.0051 (3)0.16438 (17)0.0506 (6)
H15A0.82160.01730.10840.076*
H15B0.75490.09360.16160.076*
H15C0.84110.01190.22290.076*
C160.7273 (2)0.2395 (3)0.28120 (14)0.0436 (6)
H16A0.79210.30950.28060.052*
H16B0.77780.16870.31410.052*
C170.6128 (3)0.2773 (3)0.33670 (16)0.0516 (7)
H17A0.56760.35180.30770.077*
H17B0.65070.29480.40330.077*
H17C0.54610.20970.33500.077*
C180.4283 (2)0.9270 (2)0.34998 (13)0.0304 (4)
C190.4394 (2)1.0002 (2)0.42959 (14)0.0354 (5)
H190.37751.06700.43340.043*
C200.5439 (2)0.9757 (2)0.50642 (15)0.0389 (5)
H200.55231.02730.56160.047*
C210.6324 (2)0.8802 (2)0.50295 (14)0.0374 (5)
H210.70160.86540.55550.045*
C220.6222 (2)0.8019 (2)0.42105 (13)0.0311 (4)
C230.7123 (2)0.7017 (2)0.41399 (15)0.0363 (5)
H230.78230.68470.46560.044*
C240.7002 (2)0.6289 (2)0.33414 (16)0.0396 (5)
H240.76240.56230.33050.048*
C250.5972 (2)0.6514 (2)0.25768 (15)0.0392 (5)
H250.58970.60000.20250.047*
C260.5073 (2)0.7470 (2)0.26198 (14)0.0347 (5)
H260.43670.76080.21010.042*
C270.5183 (2)0.8257 (2)0.34330 (13)0.0287 (4)
C280.2398 (2)1.0435 (2)0.26756 (14)0.0334 (5)
H280.29491.12040.28380.040*
C290.1716 (2)1.0554 (2)0.16425 (14)0.0428 (6)
H29A0.24151.07010.12250.064*
H29B0.10741.12520.15900.064*
H29C0.12210.97870.14480.064*
C300.1332 (2)1.0349 (2)0.33672 (13)0.0308 (4)
C310.0305 (2)0.9321 (3)0.41976 (15)0.0430 (6)
H31A0.09730.86430.40340.052*
H31B0.08071.01170.41080.052*
C320.0295 (3)0.9199 (3)0.52358 (14)0.0491 (6)
H32A0.06450.83540.53580.074*
H32B0.04140.93680.56410.074*
H32C0.10440.97950.53840.074*
C330.0882 (2)0.8087 (2)0.30606 (15)0.0406 (5)
H33A0.14110.82220.25220.049*
H33B0.00330.77740.27900.049*
C340.1596 (3)0.7109 (2)0.37179 (18)0.0500 (6)
H34A0.24750.74340.40270.075*
H34B0.17540.63680.33450.075*
H34C0.10230.68910.42070.075*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0290 (7)0.0402 (9)0.0339 (7)0.0012 (7)0.0085 (6)0.0103 (6)
O20.0540 (10)0.0376 (10)0.0447 (8)0.0007 (8)0.0144 (7)0.0084 (7)
O30.0372 (8)0.0415 (9)0.0296 (7)0.0074 (7)0.0008 (6)0.0029 (6)
O40.0492 (9)0.0325 (9)0.0410 (8)0.0076 (8)0.0058 (7)0.0005 (7)
N10.0358 (9)0.0380 (11)0.0288 (8)0.0021 (8)0.0035 (7)0.0044 (8)
N20.0354 (10)0.0329 (10)0.0298 (8)0.0045 (8)0.0035 (7)0.0006 (8)
C10.0278 (10)0.0350 (11)0.0228 (8)0.0022 (9)0.0037 (7)0.0007 (8)
C20.0393 (11)0.0358 (12)0.0255 (8)0.0017 (10)0.0055 (8)0.0041 (8)
C30.0359 (11)0.0457 (14)0.0294 (10)0.0117 (10)0.0016 (8)0.0033 (10)
C40.0284 (10)0.0504 (15)0.0324 (10)0.0008 (10)0.0059 (8)0.0066 (10)
C50.0299 (10)0.0344 (11)0.0253 (9)0.0048 (9)0.0062 (7)0.0053 (8)
C60.0374 (12)0.0414 (13)0.0327 (10)0.0111 (11)0.0119 (8)0.0079 (9)
C70.0579 (15)0.0311 (12)0.0330 (10)0.0103 (11)0.0158 (10)0.0015 (9)
C80.0498 (13)0.0315 (12)0.0342 (10)0.0028 (11)0.0051 (9)0.0029 (9)
C90.0350 (11)0.0326 (11)0.0296 (9)0.0004 (10)0.0055 (8)0.0010 (9)
C100.0300 (10)0.0307 (11)0.0216 (8)0.0031 (9)0.0048 (7)0.0037 (8)
C110.0370 (11)0.0389 (13)0.0333 (10)0.0089 (10)0.0079 (8)0.0023 (9)
C120.0352 (12)0.0755 (19)0.0383 (11)0.0150 (13)0.0021 (9)0.0107 (12)
C130.0287 (10)0.0413 (13)0.0325 (10)0.0028 (10)0.0095 (8)0.0055 (9)
C140.0443 (13)0.0376 (13)0.0410 (11)0.0058 (11)0.0063 (10)0.0001 (10)
C150.0575 (15)0.0432 (15)0.0491 (13)0.0111 (13)0.0002 (11)0.0011 (12)
C160.0463 (13)0.0534 (15)0.0297 (9)0.0013 (12)0.0007 (9)0.0041 (10)
C170.0572 (15)0.0623 (18)0.0384 (11)0.0106 (14)0.0177 (10)0.0067 (12)
C180.0275 (10)0.0353 (11)0.0292 (9)0.0017 (9)0.0061 (7)0.0024 (9)
C190.0343 (11)0.0387 (13)0.0349 (10)0.0026 (10)0.0105 (8)0.0051 (10)
C200.0380 (12)0.0475 (14)0.0318 (10)0.0073 (11)0.0073 (9)0.0090 (10)
C210.0325 (11)0.0506 (14)0.0285 (10)0.0045 (11)0.0021 (8)0.0010 (9)
C220.0275 (10)0.0363 (12)0.0306 (9)0.0052 (9)0.0079 (7)0.0042 (9)
C230.0330 (11)0.0400 (13)0.0351 (10)0.0011 (10)0.0021 (8)0.0102 (10)
C240.0398 (12)0.0334 (12)0.0468 (12)0.0043 (10)0.0097 (10)0.0057 (10)
C250.0458 (13)0.0350 (13)0.0372 (10)0.0017 (11)0.0067 (9)0.0042 (10)
C260.0361 (11)0.0368 (12)0.0304 (9)0.0021 (10)0.0022 (8)0.0002 (9)
C270.0281 (10)0.0324 (11)0.0267 (9)0.0031 (9)0.0072 (7)0.0031 (8)
C280.0338 (11)0.0313 (12)0.0353 (10)0.0006 (9)0.0056 (8)0.0034 (9)
C290.0485 (14)0.0482 (15)0.0316 (10)0.0072 (12)0.0047 (9)0.0074 (10)
C300.0298 (11)0.0340 (12)0.0273 (9)0.0037 (9)0.0010 (8)0.0033 (9)
C310.0321 (12)0.0571 (16)0.0409 (11)0.0066 (11)0.0089 (9)0.0061 (11)
C320.0525 (16)0.0614 (17)0.0342 (11)0.0045 (14)0.0092 (10)0.0026 (12)
C330.0489 (13)0.0338 (12)0.0376 (11)0.0094 (11)0.0008 (9)0.0059 (10)
C340.0729 (17)0.0295 (12)0.0474 (13)0.0043 (12)0.0074 (12)0.0008 (11)
Geometric parameters (Å, º) top
O1—C11.376 (2)C16—C171.517 (3)
O1—C111.428 (3)C16—H16A0.9900
O2—C131.233 (3)C16—H16B0.9900
O3—C181.376 (2)C17—H17A0.9800
O3—C281.426 (3)C17—H17B0.9800
O4—C301.233 (3)C17—H17C0.9800
N1—C131.337 (3)C18—C191.364 (3)
N1—C161.471 (3)C18—C271.419 (3)
N1—C141.472 (3)C19—C201.414 (3)
N2—C301.339 (3)C19—H190.9500
N2—C331.464 (3)C20—C211.355 (3)
N2—C311.472 (3)C20—H200.9500
C1—C21.364 (3)C21—C221.422 (3)
C1—C101.423 (3)C21—H210.9500
C2—C31.414 (3)C22—C231.411 (3)
C2—H20.9500C22—C271.418 (3)
C3—C41.357 (3)C23—C241.364 (3)
C3—H30.9500C23—H230.9500
C4—C51.408 (3)C24—C251.398 (3)
C4—H40.9500C24—H240.9500
C5—C61.417 (3)C25—C261.366 (3)
C5—C101.423 (3)C25—H250.9500
C6—C71.361 (3)C26—C271.418 (3)
C6—H60.9500C26—H260.9500
C7—C81.397 (3)C28—C291.524 (3)
C7—H70.9500C28—C301.534 (3)
C8—C91.371 (3)C28—H281.0000
C8—H80.9500C29—H29A0.9800
C9—C101.409 (3)C29—H29B0.9800
C9—H90.9500C29—H29C0.9800
C11—C121.519 (3)C31—C321.507 (3)
C11—C131.533 (3)C31—H31A0.9900
C11—H111.0000C31—H31B0.9900
C12—H12A0.9800C32—H32A0.9800
C12—H12B0.9800C32—H32B0.9800
C12—H12C0.9800C32—H32C0.9800
C14—C151.516 (3)C33—C341.512 (3)
C14—H14A0.9900C33—H33A0.9900
C14—H14B0.9900C33—H33B0.9900
C15—H15A0.9800C34—H34A0.9800
C15—H15B0.9800C34—H34B0.9800
C15—H15C0.9800C34—H34C0.9800
C1—O1—C11117.92 (16)H17A—C17—H17B109.5
C18—O3—C28118.37 (16)C16—C17—H17C109.5
C13—N1—C16117.11 (19)H17A—C17—H17C109.5
C13—N1—C14126.36 (17)H17B—C17—H17C109.5
C16—N1—C14116.26 (18)C19—C18—O3125.1 (2)
C30—N2—C33126.51 (17)C19—C18—C27121.31 (18)
C30—N2—C31116.8 (2)O3—C18—C27113.55 (17)
C33—N2—C31116.49 (19)C18—C19—C20119.3 (2)
C2—C1—O1125.30 (18)C18—C19—H19120.3
C2—C1—C10121.22 (17)C20—C19—H19120.3
O1—C1—C10113.47 (17)C21—C20—C19121.3 (2)
C1—C2—C3119.63 (19)C21—C20—H20119.3
C1—C2—H2120.2C19—C20—H20119.3
C3—C2—H2120.2C20—C21—C22120.38 (19)
C4—C3—C2120.9 (2)C20—C21—H21119.8
C4—C3—H3119.6C22—C21—H21119.8
C2—C3—H3119.6C23—C22—C27118.64 (19)
C3—C4—C5120.68 (19)C23—C22—C21122.44 (19)
C3—C4—H4119.7C27—C22—C21118.9 (2)
C5—C4—H4119.7C24—C23—C22121.0 (2)
C4—C5—C6122.21 (19)C24—C23—H23119.5
C4—C5—C10119.48 (18)C22—C23—H23119.5
C6—C5—C10118.30 (19)C23—C24—C25120.6 (2)
C7—C6—C5121.2 (2)C23—C24—H24119.7
C7—C6—H6119.4C25—C24—H24119.7
C5—C6—H6119.4C26—C25—C24120.3 (2)
C6—C7—C8120.2 (2)C26—C25—H25119.9
C6—C7—H7119.9C24—C25—H25119.9
C8—C7—H7119.9C25—C26—C27120.57 (19)
C9—C8—C7120.7 (2)C25—C26—H26119.7
C9—C8—H8119.7C27—C26—H26119.7
C7—C8—H8119.7C22—C27—C26118.95 (19)
C8—C9—C10120.5 (2)C22—C27—C18118.71 (18)
C8—C9—H9119.8C26—C27—C18122.33 (17)
C10—C9—H9119.8O3—C28—C29106.63 (17)
C9—C10—C5119.18 (18)O3—C28—C30115.67 (17)
C9—C10—C1122.77 (17)C29—C28—C30111.22 (17)
C5—C10—C1118.05 (18)O3—C28—H28107.7
O1—C11—C12106.54 (18)C29—C28—H28107.7
O1—C11—C13116.58 (17)C30—C28—H28107.7
C12—C11—C13110.83 (16)C28—C29—H29A109.5
O1—C11—H11107.5C28—C29—H29B109.5
C12—C11—H11107.5H29A—C29—H29B109.5
C13—C11—H11107.5C28—C29—H29C109.5
C11—C12—H12A109.5H29A—C29—H29C109.5
C11—C12—H12B109.5H29B—C29—H29C109.5
H12A—C12—H12B109.5O4—C30—N2122.14 (19)
C11—C12—H12C109.5O4—C30—C28115.79 (19)
H12A—C12—H12C109.5N2—C30—C28121.99 (18)
H12B—C12—H12C109.5N2—C31—C32113.77 (18)
O2—C13—N1121.89 (19)N2—C31—H31A108.8
O2—C13—C11115.7 (2)C32—C31—H31A108.8
N1—C13—C11122.3 (2)N2—C31—H31B108.8
N1—C14—C15112.8 (2)C32—C31—H31B108.8
N1—C14—H14A109.0H31A—C31—H31B107.7
C15—C14—H14A109.0C31—C32—H32A109.5
N1—C14—H14B109.0C31—C32—H32B109.5
C15—C14—H14B109.0H32A—C32—H32B109.5
H14A—C14—H14B107.8C31—C32—H32C109.5
C14—C15—H15A109.5H32A—C32—H32C109.5
C14—C15—H15B109.5H32B—C32—H32C109.5
H15A—C15—H15B109.5N2—C33—C34113.70 (18)
C14—C15—H15C109.5N2—C33—H33A108.8
H15A—C15—H15C109.5C34—C33—H33A108.8
H15B—C15—H15C109.5N2—C33—H33B108.8
N1—C16—C17112.36 (19)C34—C33—H33B108.8
N1—C16—H16A109.1H33A—C33—H33B107.7
C17—C16—H16A109.1C33—C34—H34A109.5
N1—C16—H16B109.1C33—C34—H34B109.5
C17—C16—H16B109.1H34A—C34—H34B109.5
H16A—C16—H16B107.9C33—C34—H34C109.5
C16—C17—H17A109.5H34A—C34—H34C109.5
C16—C17—H17B109.5H34B—C34—H34C109.5
C11—O1—C1—C212.6 (3)C28—O3—C18—C192.2 (3)
C11—O1—C1—C10168.54 (16)C28—O3—C18—C27177.86 (17)
O1—C1—C2—C3176.36 (18)O3—C18—C19—C20179.1 (2)
C10—C1—C2—C32.4 (3)C27—C18—C19—C200.9 (3)
C1—C2—C3—C40.3 (3)C18—C19—C20—C210.7 (3)
C2—C3—C4—C51.4 (3)C19—C20—C21—C220.2 (3)
C3—C4—C5—C6178.1 (2)C20—C21—C22—C23179.8 (2)
C3—C4—C5—C101.1 (3)C20—C21—C22—C270.1 (3)
C4—C5—C6—C7178.3 (2)C27—C22—C23—C240.1 (3)
C10—C5—C6—C71.0 (3)C21—C22—C23—C24179.6 (2)
C5—C6—C7—C80.5 (3)C22—C23—C24—C250.6 (3)
C6—C7—C8—C90.1 (3)C23—C24—C25—C260.1 (3)
C7—C8—C9—C100.2 (3)C24—C25—C26—C270.9 (3)
C8—C9—C10—C50.3 (3)C23—C22—C27—C260.9 (3)
C8—C9—C10—C1179.57 (19)C21—C22—C27—C26179.40 (19)
C4—C5—C10—C9178.36 (18)C23—C22—C27—C18179.53 (18)
C6—C5—C10—C90.9 (3)C21—C22—C27—C180.2 (3)
C4—C5—C10—C10.9 (3)C25—C26—C27—C221.4 (3)
C6—C5—C10—C1179.84 (17)C25—C26—C27—C18179.0 (2)
C2—C1—C10—C9176.56 (18)C19—C18—C27—C220.7 (3)
O1—C1—C10—C94.5 (3)O3—C18—C27—C22179.40 (17)
C2—C1—C10—C52.7 (3)C19—C18—C27—C26178.9 (2)
O1—C1—C10—C5176.23 (16)O3—C18—C27—C261.1 (3)
C1—O1—C11—C12166.67 (16)C18—O3—C28—C29166.45 (18)
C1—O1—C11—C1369.0 (2)C18—O3—C28—C3069.3 (2)
C16—N1—C13—O21.0 (3)C33—N2—C30—O4172.35 (19)
C14—N1—C13—O2172.9 (2)C31—N2—C30—O42.1 (3)
C16—N1—C13—C11178.96 (18)C33—N2—C30—C284.3 (3)
C14—N1—C13—C115.1 (3)C31—N2—C30—C28178.82 (17)
O1—C11—C13—O2141.9 (2)O3—C28—C30—O4143.88 (18)
C12—C11—C13—O296.0 (2)C29—C28—C30—O494.3 (2)
O1—C11—C13—N139.9 (3)O3—C28—C30—N239.2 (3)
C12—C11—C13—N182.1 (3)C29—C28—C30—N282.6 (2)
C13—N1—C14—C15110.4 (2)C30—N2—C31—C3285.6 (3)
C16—N1—C14—C1575.7 (3)C33—N2—C31—C3299.4 (3)
C13—N1—C16—C1781.5 (3)C30—N2—C33—C34112.8 (2)
C14—N1—C16—C1793.0 (3)C31—N2—C33—C3472.7 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C25—H25···O20.952.413.228 (3)144
C6—H6···O2i0.952.533.388 (3)150
C7—H7···O4ii0.952.603.481 (3)154
C23—H23···O4iii0.952.463.376 (3)161
Symmetry codes: (i) x+2, y1/2, z; (ii) x+1, y3/2, z; (iii) x+1, y1/2, z+1.

Experimental details

Crystal data
Chemical formulaC17H21NO2
Mr271.35
Crystal system, space groupMonoclinic, P21
Temperature (K)173
a, b, c (Å)9.8733 (3), 10.7710 (4), 14.1044 (5)
β (°) 97.943 (2)
V3)1485.55 (9)
Z4
Radiation typeMo Kα
µ (mm1)0.08
Crystal size (mm)0.35 × 0.18 × 0.15
Data collection
DiffractometerBruker APEXII CCD
diffractometer
Absorption correctionMulti-scan
(SADABS; Bruker, 2009)
Tmin, Tmax0.973, 0.988
No. of measured, independent and
observed [I > 2σ(I)] reflections
26573, 3897, 3297
Rint0.041
(sin θ/λ)max1)0.668
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.037, 0.083, 1.03
No. of reflections3897
No. of parameters367
No. of restraints1
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.15, 0.16

Computer programs: APEX2 (Bruker, 2009), SAINT (Bruker, 2009), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C25—H25···O20.952.413.228 (3)143.5
C6—H6···O2i0.952.533.388 (3)150.1
C7—H7···O4ii0.952.603.481 (3)154.0
C23—H23···O4iii0.952.463.376 (3)160.9
Symmetry codes: (i) x+2, y1/2, z; (ii) x+1, y3/2, z; (iii) x+1, y1/2, z+1.
 

Acknowledgements

This research was supported by the Basic Science Research Program through the National Research Foundation of Korea (NRF) funded by the Ministry of Education, Science and Technology (No. 2012M2B2A4029305).

References

First citationAu-Yeung, H. Y., Pengo, P., Pantos, G. D., Otto, S. & Sanders, J. K. (2009). Chem. Commun. pp. 419–421.
First citationBruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
First citationFreeman, J. A. (1986). Can. J. Plant Sci. 66, 141-152.  CrossRef CAS
First citationGless, R. D. Jr (1986). Synth. Commun. 16, 633–638.  CrossRef CAS Web of Science
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals

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