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The title amide, C21H23NO2, (I), does not photocyclize in the solid state. The methoxy group is involved in intermolecular steric interactions and so prevents the rotation of the N-phenyl group in the crystal.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270100004029/qa0250sup1.cif
Contains datablocks enamid4, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108270100004029/qa0250Isup2.hkl
Contains datablock I

CCDC reference: 144710

Experimental top

The title compound was prepared by one of the authors (HA) in a study on photocyclization of enamides and thioamides in the solid state (Aoyama, 2000). Crystals were grown from a hexane solution.

Refinement top

X-ray intensity data were measured for +h,+k,±l (θ < 75°) and for +h,-k,±l (θ < 30°). The completeness of symmetry unique reflections (θ < 75°) was 93.3%, which was due to the blind region of the low-temperature apparatus.

All H-atom positional parameters were calculated geometrically and fixed with Uiso(H) = 1.2Ueq(parent atom). For the cyclohexene ring, the C5—C6 and C5C10 axes were assigned to be single and double bonds, respectively, based on the bond lengths [1.486 (3) Å and 1.340 (3) Å, respectively]. The short C7—C8 bond length of 1.366 (5) Å may be an artifact due to the conformational disorder of the six-membered ring.

Computing details top

Data collection: MSC/AFC Diffractometer Control Software (Molecular Structure Corporation, 1993); cell refinement: MSC/AFC Diffractometer Control Software; data reduction: TEXSAN (Molecular Structure Corporation, 1999); program(s) used to solve structure: SIR92 (Altomare et al., 1994); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); software used to prepare material for publication: TEXSAN.

Cyclohex-1-enecarboxylic acid benzyl-(2-methoxy-phenyl)-amide top
Crystal data top
C21H23NO2Dx = 1.208 Mg m3
Mr = 321.42Cu Kα radiation, λ = 1.54184 Å
Monoclinic, P21/nCell parameters from 25 reflections
a = 10.485 (3) Åθ = 28.8–30.0°
b = 8.179 (1) ŵ = 0.61 mm1
c = 20.985 (1) ÅT = 248 K
β = 100.98 (1)°Plate-like, colourless
V = 1766.7 (6) Å30.5 × 0.5 × 0.05 mm
Z = 4
Data collection top
Rigaku AFC-7R
diffractometer
Rint = 0.010
θ–2θ scansθmax = 75.0°, θmin = 2.5°
Absorption correction: integration
(Coppens et al., 1965)
h = 013
Tmin = 0.765, Tmax = 0.969k = 510
4069 measured reflectionsl = 2626
3388 independent reflections3 standard reflections every 150 reflections
2631 reflections with I > 2σ(I) intensity decay: none
Refinement top
Refinement on F2H-atom parameters not refined
R[F2 > 2σ(F2)] = 0.055 w = 1/[σ2(Fo2) + (0.0708P)2 + 0.9854P]
where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.159(Δ/σ)max = 0.001
S = 1.04Δρmax = 0.48 e Å3
3388 reflectionsΔρmin = 0.46 e Å3
217 parameters
Crystal data top
C21H23NO2V = 1766.7 (6) Å3
Mr = 321.42Z = 4
Monoclinic, P21/nCu Kα radiation
a = 10.485 (3) ŵ = 0.61 mm1
b = 8.179 (1) ÅT = 248 K
c = 20.985 (1) Å0.5 × 0.5 × 0.05 mm
β = 100.98 (1)°
Data collection top
Rigaku AFC-7R
diffractometer
2631 reflections with I > 2σ(I)
Absorption correction: integration
(Coppens et al., 1965)
Rint = 0.010
Tmin = 0.765, Tmax = 0.9693 standard reflections every 150 reflections
4069 measured reflections intensity decay: none
3388 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.055217 parameters
wR(F2) = 0.159H-atom parameters not refined
S = 1.04Δρmax = 0.48 e Å3
3388 reflectionsΔρmin = 0.46 e Å3
Special details top

Refinement. Refinement was based on F2 against all reflections. The weighted R-factor (wR) and goodness of fit (S) were based on F2, and conventional R-factor (R) was calculated on F, with F set to zero for negative F2. The threshold expression of I > 2σ(I) was used only for calculating R-factor(gt).

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
O10.1455 (2)0.5217 (2)0.21606 (7)0.0542 (4)
O20.1286 (2)0.7791 (2)0.03870 (7)0.0548 (4)
N30.0690 (2)0.7132 (2)0.14063 (8)0.0414 (4)
C40.0776 (2)0.6423 (2)0.20037 (9)0.0402 (4)
C50.0009 (2)0.7149 (2)0.24562 (9)0.0396 (4)
C60.0715 (2)0.7562 (3)0.3116 (1)0.0538 (6)
C70.0139 (3)0.8068 (5)0.3572 (2)0.102 (1)
C80.1367 (3)0.8629 (7)0.3338 (2)0.120 (2)
C90.2133 (2)0.7890 (4)0.2737 (1)0.0699 (7)
C100.1301 (2)0.7298 (3)0.2281 (1)0.0530 (6)
C110.1358 (2)0.6327 (3)0.0937 (1)0.0496 (5)
C120.2727 (2)0.6901 (3)0.0950 (1)0.0448 (5)
C130.3302 (3)0.6611 (3)0.0413 (1)0.0562 (6)
C140.4567 (3)0.7111 (4)0.0417 (1)0.0729 (8)
C150.5267 (3)0.7923 (4)0.0939 (2)0.0729 (8)
C160.4710 (2)0.8226 (3)0.1473 (1)0.0651 (7)
C170.3455 (2)0.7701 (3)0.1477 (1)0.0523 (5)
C180.0237 (2)0.8781 (2)0.12751 (9)0.0389 (4)
C190.0782 (2)1.0045 (3)0.16678 (9)0.0421 (4)
C200.0349 (2)1.1635 (3)0.1557 (1)0.0517 (5)
C210.0625 (2)1.1956 (3)0.1030 (1)0.0567 (6)
C220.1173 (2)1.0698 (3)0.0626 (1)0.0519 (5)
C230.0758 (2)0.9114 (3)0.07480 (9)0.0431 (5)
C240.2178 (2)0.8132 (4)0.0198 (1)0.0604 (6)
H6A0.12370.66200.32890.0580*
H6B0.12990.84560.30820.0580*
H7A0.02440.70520.38270.1193*
H7B0.03570.88130.38800.1193*
H8A0.18970.86510.36640.1291*
H8B0.12700.98320.32220.1291*
H9A0.27680.86470.25090.0800*
H9B0.25950.69600.28700.0800*
H100.17190.70220.18410.0555*
H11A0.13920.51760.10260.0532*
H11B0.08690.65140.05070.0532*
H130.28290.60150.00420.0606*
H140.49510.68850.00460.0799*
H150.61430.83430.09280.0777*
H160.52090.87820.18560.0735*
H170.30720.78960.18540.0557*
H190.14750.98150.20320.0454*
H200.07221.25140.18400.0557*
H210.09091.30640.09450.0630*
H220.18541.09380.02550.0555*
H24A0.29140.87330.01040.0672*
H24B0.24930.71180.04090.0672*
H24C0.17700.87610.04880.0672*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0663 (10)0.0408 (8)0.0536 (9)0.0105 (7)0.0064 (7)0.0049 (7)
O20.0556 (9)0.0578 (10)0.0458 (8)0.0078 (7)0.0032 (7)0.0016 (7)
N30.0458 (9)0.0428 (9)0.0354 (8)0.0022 (7)0.0074 (7)0.0001 (7)
C40.042 (1)0.0368 (10)0.0395 (10)0.0038 (8)0.0010 (8)0.0008 (8)
C50.043 (1)0.0370 (10)0.0378 (10)0.0043 (8)0.0061 (8)0.0048 (8)
C60.052 (1)0.062 (1)0.046 (1)0.001 (1)0.0043 (10)0.001 (1)
C70.073 (2)0.167 (4)0.062 (2)0.017 (2)0.004 (1)0.049 (2)
C80.066 (2)0.216 (5)0.080 (2)0.017 (3)0.016 (2)0.061 (3)
C90.044 (1)0.098 (2)0.069 (2)0.004 (1)0.014 (1)0.006 (1)
C100.048 (1)0.065 (1)0.045 (1)0.012 (1)0.0069 (9)0.000 (1)
C110.058 (1)0.051 (1)0.040 (1)0.003 (1)0.0088 (9)0.0072 (9)
C120.052 (1)0.043 (1)0.040 (1)0.0108 (9)0.0115 (9)0.0054 (9)
C130.069 (1)0.061 (1)0.041 (1)0.013 (1)0.015 (1)0.005 (1)
C140.075 (2)0.089 (2)0.064 (2)0.015 (2)0.037 (1)0.015 (1)
C150.057 (1)0.085 (2)0.081 (2)0.001 (1)0.023 (1)0.009 (2)
C160.053 (1)0.070 (2)0.072 (2)0.003 (1)0.010 (1)0.004 (1)
C170.048 (1)0.061 (1)0.048 (1)0.007 (1)0.0094 (10)0.005 (1)
C180.042 (1)0.040 (1)0.0368 (9)0.0013 (8)0.0125 (8)0.0034 (8)
C190.043 (1)0.045 (1)0.0393 (10)0.0034 (9)0.0090 (8)0.0014 (9)
C200.060 (1)0.041 (1)0.056 (1)0.0056 (10)0.016 (1)0.0050 (10)
C210.063 (1)0.045 (1)0.064 (1)0.007 (1)0.016 (1)0.009 (1)
C220.049 (1)0.055 (1)0.050 (1)0.005 (1)0.0056 (10)0.012 (1)
C230.043 (1)0.048 (1)0.0391 (10)0.0040 (9)0.0101 (8)0.0026 (9)
C240.048 (1)0.082 (2)0.047 (1)0.005 (1)0.0002 (10)0.004 (1)
Geometric parameters (Å, º) top
O1—C41.224 (2)C12—C131.395 (3)
O2—C231.375 (3)C12—C171.384 (3)
O2—C241.422 (3)C13—C141.387 (4)
N3—C41.369 (3)C13—H130.97
N3—C111.468 (3)C14—C151.368 (4)
N3—C181.439 (3)C14—H140.96
C4—C51.493 (3)C15—C161.382 (4)
C5—C61.486 (3)C15—H150.98
C5—C101.340 (3)C16—C171.385 (4)
C6—C71.488 (4)C16—H160.98
C6—H6A0.97C17—H170.97
C6—H6B0.97C18—C191.377 (3)
C7—C81.366 (5)C18—C231.395 (3)
C7—H7A1.01C19—C201.383 (3)
C7—H7B0.97C19—H190.97
C8—C91.488 (4)C20—C211.379 (3)
C8—H8A0.96C20—H200.97
C8—H8B1.02C21—C221.387 (3)
C9—C101.493 (4)C21—H210.96
C9—H9A0.97C22—C231.375 (3)
C9—H9B0.97C22—H220.97
C10—H100.97C24—H24A0.97
C11—C121.506 (3)C24—H24B0.97
C11—H11A0.96C24—H24C0.96
C11—H11B0.96
C23—O2—C24116.8 (2)C11—C12—C13119.3 (2)
C4—N3—C11117.8 (2)C11—C12—C17122.7 (2)
C4—N3—C18122.3 (2)C13—C12—C17117.9 (2)
C11—N3—C18118.3 (2)C12—C13—C14120.3 (2)
O1—C4—N3121.4 (2)C12—C13—H13120
O1—C4—C5120.8 (2)C14—C13—H13120
N3—C4—C5117.7 (2)C13—C14—C15121.0 (3)
C4—C5—C6116.0 (2)C13—C14—H14119
C4—C5—C10120.9 (2)C15—C14—H14120
C6—C5—C10123.0 (2)C14—C15—C16119.4 (3)
C5—C6—C7113.5 (2)C14—C15—H15121
C5—C6—H6A109C16—C15—H15120
C5—C6—H6B109C15—C16—C17119.9 (2)
C7—C6—H6A110C15—C16—H16120
C7—C6—H6B108C17—C16—H16120
H6A—C6—H6B108C12—C17—C16121.5 (2)
C6—C7—C8120.3 (3)C12—C17—H17119
C6—C7—H7A105C16—C17—H17120
C6—C7—H7B107N3—C18—C19120.3 (2)
C8—C7—H7A106N3—C18—C23120.3 (2)
C8—C7—H7B112C19—C18—C23119.4 (2)
H7A—C7—H7B105C18—C19—C20121.3 (2)
C7—C8—C9119.1 (4)C18—C19—H19119
C7—C8—H8A113C20—C19—H19119
C7—C8—H8B106C19—C20—C21118.9 (2)
C9—C8—H8A109C19—C20—H20121
C9—C8—H8B105C21—C20—H20120
H8A—C8—H8B104C20—C21—C22120.4 (2)
C8—C9—C10112.8 (2)C20—C21—H21119
C8—C9—H9A112C22—C21—H21121
C8—C9—H9B107C21—C22—C23120.4 (2)
C10—C9—H9A109C21—C22—H22120
C10—C9—H9B108C23—C22—H22120
H9A—C9—H9B108O2—C23—C18116.4 (2)
C5—C10—C9122.5 (2)O2—C23—C22124.0 (2)
C5—C10—H10119C18—C23—C22119.6 (2)
C9—C10—H10118O2—C24—H24A110
N3—C11—C12115.0 (2)O2—C24—H24B110
N3—C11—H11A108O2—C24—H24C111
N3—C11—H11B109H24A—C24—H24B108
C12—C11—H11A108H24A—C24—H24C109
C12—C11—H11B108H24B—C24—H24C109
H11A—C11—H11B109

Experimental details

Crystal data
Chemical formulaC21H23NO2
Mr321.42
Crystal system, space groupMonoclinic, P21/n
Temperature (K)248
a, b, c (Å)10.485 (3), 8.179 (1), 20.985 (1)
β (°) 100.98 (1)
V3)1766.7 (6)
Z4
Radiation typeCu Kα
µ (mm1)0.61
Crystal size (mm)0.5 × 0.5 × 0.05
Data collection
DiffractometerRigaku AFC-7R
diffractometer
Absorption correctionIntegration
(Coppens et al., 1965)
Tmin, Tmax0.765, 0.969
No. of measured, independent and
observed [I > 2σ(I)] reflections
4069, 3388, 2631
Rint0.010
(sin θ/λ)max1)0.626
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.055, 0.159, 1.04
No. of reflections3388
No. of parameters217
No. of restraints?
H-atom treatmentH-atom parameters not refined
Δρmax, Δρmin (e Å3)0.48, 0.46

Computer programs: MSC/AFC Diffractometer Control Software (Molecular Structure Corporation, 1993), MSC/AFC Diffractometer Control Software, TEXSAN (Molecular Structure Corporation, 1999), SIR92 (Altomare et al., 1994), SHELXL97 (Sheldrick, 1997), TEXSAN.

Selected bond lengths (Å) top
O1—C41.224 (2)C6—C71.488 (4)
N3—C41.369 (3)C7—C81.366 (5)
C4—C51.493 (3)C8—C91.488 (4)
C5—C61.486 (3)C9—C101.493 (4)
C5—C101.340 (3)
 

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