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Methyl 2-benzamido-4-(3,4-dimeth­oxy­phenyl)-5-methyl­benz­o­ate, C24H23NO5, (Ia), and N-{5-benzoyl-2-[(Z)-2-meth­oxy­ethen­yl]-4-methyl­phenyl}benzamide, C24H21NO3, (IIa), were formed via a Diels–Alder reaction of appropriately substituted 2H-pyran-2-ones and methyl propiolate or (Z)-1-meth­oxy­but-1-en-3-yne, respectively. Each of these cyclo­additions might yield two different regioisomers, but just one was obtained in each case. In (Ia), an intra­molecular N—H...O hydrogen bond closes a six-membered ring. A chain is formed due to aromatic π–π inter­actions, and a three-dimensional framework structure is formed by a combination of C—H...O and C—H...π(arene) hydrogen bonds. Compound (IIa) was formed not only regioselectively but also chemoselectively, with just the triple bond reacting and the double bond remaining unchanged. Compound (IIa) crystallizes as N—H...O hydrogen-bonded dimers stabilized by aromatic π–π inter­actions. Dimers of (IIa) are connected into a chain by weak C—H...π(arene) inter­actions.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270111015794/ku3044sup1.cif
Contains datablocks global, Ia, IIa

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108270111015794/ku3044Iasup2.hkl
Contains datablock Ia

cml

Chemical Markup Language (CML) file https://doi.org/10.1107/S0108270111015794/ku3044Iasup3.cml
Supplementary material

cml

Chemical Markup Language (CML) file https://doi.org/10.1107/S0108270111015794/ku3044IIasup5.cml
Supplementary material

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108270111015794/ku3044IIasup4.hkl
Contains datablock IIa

CCDC references: 833416; 833417

Computing details top

For both compounds, data collection: COLLECT (Nonius, 1998); cell refinement: DENZO-SMN (Otwinowski & Minor, 1997); data reduction: DENZO-SMN (Otwinowski & Minor, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997) and DIAMOND (Brandenburg, 1999); software used to prepare material for publication: WinGX (Farrugia, 1999) and publCIF (Westrip, 2010).

(Ia) Methyl 2-benzamido-4-(3,4-dimethoxyphenyl)-5-methylbenzoate top
Crystal data top
C24H23NO5F(000) = 856
Mr = 405.43Dx = 1.344 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 4631 reflections
a = 7.6516 (1) Åθ = 2.6–27.5°
b = 14.7810 (3) ŵ = 0.09 mm1
c = 17.8063 (4) ÅT = 293 K
β = 95.8175 (8)°Prism, colourless
V = 2003.49 (7) Å30.2 × 0.2 × 0.2 mm
Z = 4
Data collection top
Nonius KappaCCD area-detector
diffractometer
4566 independent reflections
Graphite monochromator3167 reflections with I > 2σ(I)
Detector resolution: 0.055 pixels mm-1Rint = 0.033
φ and ω scansθmax = 27.5°, θmin = 3.6°
Absorption correction: multi-scan
(SCALEPACK; Otwinowski & Minor, 1997)
h = 99
Tmin = 0.981, Tmax = 0.981k = 1819
8696 measured reflectionsl = 2323
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)] = 0.046Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.126H-atom parameters constrained
S = 1.02 w = 1/[σ2(Fo2) + (0.059P)2 + 0.4255P]
where P = (Fo2 + 2Fc2)/3
4566 reflections(Δ/σ)max < 0.001
275 parametersΔρmax = 0.18 e Å3
0 restraintsΔρmin = 0.17 e Å3
Special details top

Experimental. 186 frames in 4 sets of φ scans + ω scans. Rotation/frame = 2 °. Crystal-detector distance = 35.0 mm. Measuring time = 50 s/°.

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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 > 2σ(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
N10.30792 (17)0.52864 (9)0.43674 (7)0.0380 (3)
H20.31840.47120.46070.057*
O10.25463 (18)0.40077 (8)0.53818 (7)0.0532 (3)
O20.12684 (17)0.44292 (8)0.63932 (7)0.0492 (3)
O30.3406 (2)0.61562 (8)0.33357 (7)0.0633 (4)
O40.10238 (16)1.00534 (8)0.35584 (6)0.0494 (3)
O50.25616 (17)1.11462 (7)0.45477 (7)0.0504 (3)
C10.1320 (2)0.61975 (11)0.60655 (8)0.0363 (4)
H10.09050.59750.65030.044*
C20.18995 (19)0.55772 (10)0.55571 (8)0.0327 (3)
C30.24941 (19)0.59109 (10)0.48853 (8)0.0332 (3)
C40.2505 (2)0.68393 (11)0.47678 (8)0.0361 (3)
H40.28950.70620.43260.043*
C50.19470 (19)0.74489 (10)0.52928 (8)0.0338 (3)
C60.1324 (2)0.71223 (11)0.59595 (8)0.0359 (3)
C70.1946 (2)0.45995 (11)0.57472 (9)0.0363 (4)
C80.1372 (3)0.35083 (13)0.66588 (12)0.0649 (6)
H8A0.06870.31260.63060.097*
H8B0.09230.34730.71420.097*
H8C0.25740.33130.67050.097*
C90.3473 (2)0.54225 (11)0.36497 (9)0.0382 (4)
C100.4012 (2)0.45859 (11)0.32554 (9)0.0367 (4)
C110.3653 (2)0.37167 (12)0.34866 (10)0.0483 (4)
H110.30550.36320.3910.058*
C120.4176 (3)0.29714 (14)0.30929 (11)0.0596 (5)
H120.39240.23910.32520.071*
C130.5069 (2)0.30905 (15)0.24645 (11)0.0587 (5)
H130.54290.25910.22020.07*
C140.5425 (2)0.39501 (15)0.22288 (10)0.0551 (5)
H140.60270.4030.18050.066*
C150.4898 (2)0.46981 (13)0.26151 (9)0.0455 (4)
H150.51350.52770.24470.055*
C160.2070 (2)0.84353 (10)0.51266 (8)0.0343 (3)
C170.1448 (2)0.87694 (10)0.44148 (8)0.0343 (3)
H170.09170.83750.40540.041*
C180.1608 (2)0.96744 (10)0.42373 (8)0.0355 (4)
C190.24404 (19)1.02684 (10)0.47741 (9)0.0368 (4)
C200.3070 (2)0.99382 (11)0.54698 (9)0.0408 (4)
H200.36321.03280.58270.049*
C210.2880 (2)0.90318 (11)0.56481 (9)0.0407 (4)
H210.33040.88240.61250.049*
C220.0106 (3)0.95324 (14)0.30494 (10)0.0559 (5)
H22A0.05250.90210.28820.084*
H22B0.05210.98970.26220.084*
H22C0.10870.93250.32980.084*
C230.3186 (3)1.17891 (12)0.51055 (12)0.0615 (5)
H23A0.43931.16630.52740.092*
H23B0.24961.17520.55260.092*
H23C0.30921.23860.48940.092*
C240.0653 (2)0.77239 (12)0.65522 (9)0.0469 (4)
H24A0.0160.73920.68230.07*
H24B0.0070.82390.63130.07*
H24C0.16210.79240.68970.07*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N10.0548 (8)0.0281 (7)0.0324 (7)0.0019 (6)0.0110 (6)0.0006 (5)
O10.0810 (9)0.0292 (6)0.0526 (7)0.0067 (6)0.0233 (6)0.0034 (5)
O20.0737 (8)0.0322 (6)0.0443 (7)0.0007 (6)0.0195 (6)0.0097 (5)
O30.1125 (12)0.0366 (7)0.0451 (7)0.0072 (7)0.0290 (7)0.0083 (6)
O40.0683 (8)0.0389 (7)0.0395 (6)0.0006 (6)0.0012 (5)0.0074 (5)
O50.0658 (8)0.0259 (6)0.0597 (8)0.0036 (6)0.0069 (6)0.0031 (5)
C10.0443 (8)0.0353 (8)0.0301 (8)0.0029 (7)0.0074 (6)0.0049 (6)
C20.0384 (8)0.0279 (8)0.0317 (8)0.0008 (6)0.0028 (6)0.0033 (6)
C30.0399 (8)0.0292 (8)0.0308 (8)0.0017 (6)0.0046 (6)0.0011 (6)
C40.0465 (9)0.0307 (8)0.0318 (8)0.0025 (7)0.0073 (6)0.0022 (6)
C50.0391 (8)0.0286 (8)0.0335 (8)0.0008 (6)0.0024 (6)0.0002 (6)
C60.0427 (8)0.0320 (8)0.0329 (8)0.0040 (7)0.0042 (6)0.0017 (6)
C70.0413 (8)0.0322 (8)0.0354 (8)0.0005 (7)0.0033 (6)0.0033 (7)
C80.0964 (15)0.0392 (11)0.0615 (12)0.0018 (11)0.0192 (11)0.0227 (9)
C90.0477 (9)0.0339 (9)0.0336 (8)0.0023 (7)0.0076 (6)0.0015 (7)
C100.0383 (8)0.0389 (9)0.0330 (8)0.0011 (7)0.0042 (6)0.0031 (7)
C110.0621 (11)0.0393 (10)0.0453 (10)0.0011 (8)0.0150 (8)0.0061 (8)
C120.0716 (13)0.0420 (11)0.0657 (13)0.0043 (9)0.0099 (10)0.0140 (9)
C130.0540 (11)0.0652 (13)0.0566 (12)0.0148 (10)0.0043 (9)0.0251 (10)
C140.0471 (10)0.0801 (15)0.0389 (9)0.0062 (10)0.0085 (7)0.0121 (10)
C150.0465 (9)0.0549 (11)0.0358 (9)0.0001 (8)0.0074 (7)0.0011 (8)
C160.0410 (8)0.0268 (8)0.0359 (8)0.0010 (6)0.0079 (6)0.0019 (6)
C170.0409 (8)0.0295 (8)0.0329 (8)0.0001 (6)0.0057 (6)0.0036 (6)
C180.0409 (8)0.0332 (9)0.0335 (8)0.0044 (7)0.0091 (6)0.0022 (6)
C190.0404 (8)0.0259 (8)0.0455 (9)0.0010 (6)0.0116 (7)0.0012 (7)
C200.0478 (9)0.0332 (9)0.0413 (9)0.0042 (7)0.0044 (7)0.0073 (7)
C210.0526 (9)0.0340 (9)0.0349 (8)0.0005 (7)0.0012 (7)0.0008 (7)
C220.0621 (11)0.0663 (13)0.0377 (10)0.0026 (10)0.0026 (8)0.0053 (9)
C230.0808 (14)0.0286 (9)0.0778 (14)0.0111 (9)0.0211 (11)0.0116 (9)
C240.0619 (11)0.0388 (9)0.0423 (9)0.0082 (8)0.0167 (8)0.0018 (8)
Geometric parameters (Å, º) top
N1—C91.3575 (19)C11—C121.386 (2)
N1—C31.4095 (19)C11—H110.93
N1—H20.95C12—C131.381 (3)
O1—C71.2082 (19)C12—H120.93
O2—C71.3329 (18)C13—C141.374 (3)
O2—C81.441 (2)C13—H130.93
O3—C91.2189 (19)C14—C151.384 (3)
O4—C181.3658 (18)C14—H140.93
O4—C221.415 (2)C15—H150.93
O5—C191.3647 (18)C16—C211.381 (2)
O5—C231.422 (2)C16—C171.398 (2)
C1—C61.380 (2)C17—C181.383 (2)
C1—C21.392 (2)C17—H170.93
C1—H10.93C18—C191.403 (2)
C2—C31.411 (2)C19—C201.373 (2)
C2—C71.484 (2)C20—C211.388 (2)
C3—C41.388 (2)C20—H200.93
C4—C51.396 (2)C21—H210.93
C4—H40.93C22—H22A0.96
C5—C61.409 (2)C22—H22B0.96
C5—C161.493 (2)C22—H22C0.96
C6—C241.509 (2)C23—H23A0.96
C8—H8A0.96C23—H23B0.96
C8—H8B0.96C23—H23C0.96
C8—H8C0.96C24—H24A0.96
C9—C101.500 (2)C24—H24B0.96
C10—C111.385 (2)C24—H24C0.96
C10—C151.394 (2)
C9—N1—C3129.39 (13)C14—C13—C12119.69 (17)
C9—N1—H2122.6C14—C13—H13120.2
C3—N1—H2108C12—C13—H13120.2
C7—O2—C8116.65 (14)C13—C14—C15120.68 (17)
C18—O4—C22117.86 (13)C13—C14—H14119.7
C19—O5—C23117.21 (14)C15—C14—H14119.7
C6—C1—C2123.93 (14)C14—C15—C10120.13 (17)
C6—C1—H1118C14—C15—H15119.9
C2—C1—H1118C10—C15—H15119.9
C1—C2—C3118.18 (14)C21—C16—C17118.19 (14)
C1—C2—C7119.68 (13)C21—C16—C5121.56 (14)
C3—C2—C7122.09 (13)C17—C16—C5120.15 (14)
C4—C3—N1122.80 (13)C18—C17—C16121.27 (14)
C4—C3—C2118.72 (13)C18—C17—H17119.4
N1—C3—C2118.48 (13)C16—C17—H17119.4
C3—C4—C5122.03 (14)O4—C18—C17124.80 (14)
C3—C4—H4119O4—C18—C19115.57 (14)
C5—C4—H4119C17—C18—C19119.62 (14)
C4—C5—C6119.71 (14)O5—C19—C20125.20 (15)
C4—C5—C16117.91 (13)O5—C19—C18115.70 (14)
C6—C5—C16122.37 (13)C20—C19—C18119.09 (14)
C1—C6—C5117.41 (13)C19—C20—C21120.96 (15)
C1—C6—C24118.83 (14)C19—C20—H20119.5
C5—C6—C24123.75 (14)C21—C20—H20119.5
O1—C7—O2122.03 (14)C16—C21—C20120.84 (15)
O1—C7—C2125.74 (14)C16—C21—H21119.6
O2—C7—C2112.22 (13)C20—C21—H21119.6
O2—C8—H8A109.5O4—C22—H22A109.5
O2—C8—H8B109.5O4—C22—H22B109.5
H8A—C8—H8B109.5H22A—C22—H22B109.5
O2—C8—H8C109.5O4—C22—H22C109.5
H8A—C8—H8C109.5H22A—C22—H22C109.5
H8B—C8—H8C109.5H22B—C22—H22C109.5
O3—C9—N1124.08 (15)O5—C23—H23A109.5
O3—C9—C10121.31 (14)O5—C23—H23B109.5
N1—C9—C10114.60 (13)H23A—C23—H23B109.5
C11—C10—C15118.75 (15)O5—C23—H23C109.5
C11—C10—C9123.59 (14)H23A—C23—H23C109.5
C15—C10—C9117.65 (15)H23B—C23—H23C109.5
C10—C11—C12120.72 (17)C6—C24—H24A109.5
C10—C11—H11119.6C6—C24—H24B109.5
C12—C11—H11119.6H24A—C24—H24B109.5
C13—C12—C11120.03 (19)C6—C24—H24C109.5
C13—C12—H12120H24A—C24—H24C109.5
C11—C12—H12120H24B—C24—H24C109.5
C6—C1—C2—C31.4 (2)C15—C10—C11—C120.5 (3)
C6—C1—C2—C7176.10 (15)C9—C10—C11—C12179.48 (17)
C9—N1—C3—C411.2 (3)C10—C11—C12—C130.2 (3)
C9—N1—C3—C2169.84 (15)C11—C12—C13—C140.5 (3)
C1—C2—C3—C41.1 (2)C12—C13—C14—C150.0 (3)
C7—C2—C3—C4176.27 (14)C13—C14—C15—C100.7 (3)
C1—C2—C3—N1179.86 (14)C11—C10—C15—C140.9 (2)
C7—C2—C3—N12.7 (2)C9—C10—C15—C14179.98 (15)
N1—C3—C4—C5178.93 (14)C4—C5—C16—C21128.69 (16)
C2—C3—C4—C50.0 (2)C6—C5—C16—C2150.1 (2)
C3—C4—C5—C61.0 (2)C4—C5—C16—C1747.6 (2)
C3—C4—C5—C16177.82 (14)C6—C5—C16—C17133.54 (16)
C2—C1—C6—C50.4 (2)C21—C16—C17—C181.1 (2)
C2—C1—C6—C24179.74 (15)C5—C16—C17—C18177.51 (13)
C4—C5—C6—C10.8 (2)C22—O4—C18—C1712.4 (2)
C16—C5—C6—C1177.97 (14)C22—O4—C18—C19168.40 (14)
C4—C5—C6—C24178.49 (15)C16—C17—C18—O4179.51 (14)
C16—C5—C6—C242.7 (2)C16—C17—C18—C191.3 (2)
C8—O2—C7—O13.3 (2)C23—O5—C19—C208.4 (2)
C8—O2—C7—C2175.43 (15)C23—O5—C19—C18171.96 (15)
C1—C2—C7—O1173.91 (16)O4—C18—C19—O50.1 (2)
C3—C2—C7—O13.5 (3)C17—C18—C19—O5179.12 (13)
C1—C2—C7—O24.8 (2)O4—C18—C19—C20179.76 (14)
C3—C2—C7—O2177.84 (13)C17—C18—C19—C200.5 (2)
C3—N1—C9—O31.6 (3)O5—C19—C20—C21179.88 (14)
C3—N1—C9—C10178.31 (14)C18—C19—C20—C210.5 (2)
O3—C9—C10—C11161.18 (18)C17—C16—C21—C200.0 (2)
N1—C9—C10—C1118.7 (2)C5—C16—C21—C20176.40 (14)
O3—C9—C10—C1517.8 (2)C19—C20—C21—C160.8 (2)
N1—C9—C10—C15162.28 (14)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H2···O10.951.832.6741 (17)146
C13—H13···O3i0.932.533.450 (2)172
C24—H24B···O5ii0.962.573.420 (2)148
Symmetry codes: (i) x+1, y1/2, z+1/2; (ii) x, y+2, z+1.
(IIa) N-{5-benzoyl-2-[(Z)-2-methoxyethenyl]-4-methylphenyl}benzamide top
Crystal data top
C24H21NO3Z = 2
Mr = 371.42F(000) = 392
Triclinic, P1Dx = 1.255 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 9.6722 (2) ÅCell parameters from 3658 reflections
b = 10.0140 (2) Åθ = 2.6–27.5°
c = 11.5677 (3) ŵ = 0.08 mm1
α = 71.422 (1)°T = 293 K
β = 84.479 (1)°Prism, colourless
γ = 67.753 (1)°0.2 × 0.2 × 0.08 mm
V = 982.60 (4) Å3
Data collection top
Nonius KappaCCD area-detector
diffractometer
4442 independent reflections
Graphite monochromator2768 reflections with I > 2σ(I)
Detector resolution: 0.055 pixels mm-1Rint = 0.030
φ and ω scansθmax = 27.5°, θmin = 3.7°
Absorption correction: multi-scan
(SCALEPACK; Otwinowski & Minor, 1997)
h = 1212
Tmin = 0.984, Tmax = 0.993k = 1212
6912 measured 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)] = 0.062Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.155H-atom parameters constrained
S = 1.03 w = 1/[σ2(Fo2) + (0.0427P)2 + 0.5035P]
where P = (Fo2 + 2Fc2)/3
4442 reflections(Δ/σ)max < 0.001
255 parametersΔρmax = 0.21 e Å3
0 restraintsΔρmin = 0.20 e Å3
Special details top

Experimental. 225 frames in 5 sets of φ scans + ω scans. Rotation/frame = 2 °. Crystal-detector distance = 35.0 mm. Measuring time = 160 s/°.

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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 > 2σ(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
N10.1805 (2)0.44050 (19)0.27717 (14)0.0437 (4)
H20.18910.35170.30330.066*
O10.52533 (19)0.2638 (2)0.64843 (15)0.0647 (5)
O20.18893 (19)0.85914 (17)0.54605 (14)0.0561 (4)
O30.2052 (3)0.6361 (2)0.12629 (15)0.0882 (7)
C10.2602 (2)0.5375 (2)0.54181 (18)0.0419 (5)
H10.33520.50450.60040.05*
C20.2821 (2)0.4592 (2)0.45615 (17)0.0390 (5)
C30.1669 (2)0.5118 (2)0.36943 (16)0.0381 (5)
C40.0387 (2)0.6350 (2)0.36939 (17)0.0400 (5)
H40.03610.66790.31070.048*
C50.0184 (2)0.7114 (2)0.45530 (17)0.0393 (5)
C60.1323 (3)0.6617 (2)0.54346 (18)0.0413 (5)
C70.4200 (3)0.3319 (2)0.4530 (2)0.0476 (5)
H70.4350.3070.38070.057*
C80.5269 (3)0.2465 (3)0.5383 (2)0.0511 (6)
H80.60810.16980.52030.061*
C90.6534 (3)0.1636 (4)0.7268 (3)0.0802 (9)
H9A0.73950.13570.67810.12*
H9B0.6360.07420.77550.12*
H9C0.67040.21370.77910.12*
C100.2005 (3)0.5095 (2)0.15966 (18)0.0494 (6)
C110.2190 (3)0.4215 (3)0.07206 (19)0.0502 (6)
C120.2980 (4)0.4566 (3)0.0323 (2)0.0759 (9)
H120.33480.53370.04650.091*
C130.3223 (4)0.3770 (4)0.1154 (2)0.0919 (12)
H130.37690.39950.18470.11*
C140.2656 (4)0.2643 (4)0.0954 (3)0.0884 (11)
H140.28060.2120.15190.106*
C150.1879 (4)0.2297 (4)0.0067 (3)0.0914 (11)
H150.15050.15310.02030.11*
C160.1641 (3)0.3086 (4)0.0908 (3)0.0715 (8)
H160.11050.28460.16040.086*
C170.1263 (3)0.8391 (2)0.45206 (19)0.0426 (5)
C180.1968 (3)0.9429 (2)0.33088 (19)0.0423 (5)
C190.1117 (3)0.9768 (2)0.2296 (2)0.0496 (6)
H190.00820.92960.23540.06*
C200.1800 (3)1.0802 (3)0.1206 (2)0.0626 (7)
H200.12241.10430.05380.075*
C210.3323 (4)1.1472 (3)0.1108 (2)0.0680 (8)
H210.37821.2160.03720.082*
C220.4177 (3)1.1132 (3)0.2093 (3)0.0667 (8)
H220.52131.15760.20160.08*
C230.3506 (3)1.0132 (3)0.3202 (2)0.0540 (6)
H230.4090.99330.38740.065*
C240.1249 (3)0.7417 (3)0.6361 (2)0.0563 (6)
H24A0.07590.70180.70730.084*
H24B0.06970.84830.60150.084*
H24C0.22430.72580.65830.084*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N10.0621 (12)0.0352 (9)0.0329 (9)0.0151 (8)0.0001 (8)0.0125 (7)
O10.0567 (11)0.0705 (11)0.0525 (10)0.0031 (9)0.0093 (8)0.0218 (8)
O20.0651 (11)0.0500 (9)0.0444 (9)0.0101 (8)0.0085 (8)0.0184 (7)
O30.168 (2)0.0583 (11)0.0455 (10)0.0539 (13)0.0230 (12)0.0166 (8)
C10.0464 (13)0.0448 (11)0.0359 (10)0.0174 (10)0.0020 (9)0.0123 (9)
C20.0449 (12)0.0373 (10)0.0343 (10)0.0153 (9)0.0047 (9)0.0110 (8)
C30.0528 (13)0.0348 (10)0.0286 (9)0.0175 (9)0.0043 (9)0.0114 (8)
C40.0500 (13)0.0369 (10)0.0307 (10)0.0139 (9)0.0034 (9)0.0084 (8)
C50.0495 (13)0.0330 (10)0.0344 (10)0.0147 (9)0.0032 (9)0.0102 (8)
C60.0523 (13)0.0412 (11)0.0348 (10)0.0205 (10)0.0038 (9)0.0141 (8)
C70.0478 (14)0.0511 (12)0.0450 (12)0.0146 (11)0.0048 (10)0.0213 (10)
C80.0473 (14)0.0513 (13)0.0538 (13)0.0143 (11)0.0047 (11)0.0204 (11)
C90.0668 (19)0.082 (2)0.0715 (18)0.0057 (15)0.0229 (15)0.0156 (15)
C100.0669 (16)0.0427 (12)0.0333 (11)0.0147 (11)0.0003 (10)0.0110 (9)
C110.0567 (15)0.0495 (13)0.0333 (11)0.0027 (11)0.0078 (10)0.0160 (9)
C120.114 (3)0.0601 (16)0.0395 (13)0.0190 (16)0.0076 (14)0.0150 (12)
C130.131 (3)0.079 (2)0.0379 (14)0.005 (2)0.0078 (16)0.0230 (14)
C140.104 (3)0.093 (2)0.0647 (19)0.005 (2)0.0143 (18)0.0533 (18)
C150.091 (2)0.116 (3)0.102 (3)0.041 (2)0.010 (2)0.079 (2)
C160.0711 (19)0.095 (2)0.0719 (17)0.0356 (16)0.0126 (14)0.0532 (16)
C170.0534 (14)0.0340 (10)0.0419 (11)0.0162 (10)0.0037 (10)0.0141 (9)
C180.0486 (13)0.0322 (10)0.0454 (12)0.0121 (9)0.0001 (10)0.0140 (9)
C190.0541 (14)0.0416 (12)0.0472 (12)0.0134 (10)0.0001 (11)0.0107 (10)
C200.079 (2)0.0510 (14)0.0473 (13)0.0202 (14)0.0005 (13)0.0055 (11)
C210.082 (2)0.0493 (14)0.0567 (16)0.0108 (14)0.0182 (15)0.0058 (12)
C220.0527 (16)0.0540 (15)0.0797 (19)0.0033 (12)0.0168 (14)0.0172 (14)
C230.0518 (15)0.0452 (12)0.0634 (15)0.0139 (11)0.0040 (12)0.0201 (11)
C240.0592 (16)0.0669 (15)0.0547 (14)0.0222 (13)0.0043 (11)0.0362 (12)
Geometric parameters (Å, º) top
N1—C101.347 (3)C11—C121.386 (4)
N1—C31.433 (2)C12—C131.385 (4)
N1—H20.8167C12—H120.93
O1—C81.337 (3)C13—C141.381 (5)
O1—C91.435 (3)C13—H130.93
O2—C171.228 (2)C14—C151.359 (5)
O3—C101.219 (3)C14—H140.93
C1—C61.387 (3)C15—C161.390 (4)
C1—C21.404 (3)C15—H150.93
C1—H10.93C16—H160.93
C2—C31.400 (3)C17—C181.493 (3)
C2—C71.462 (3)C18—C231.382 (3)
C3—C41.379 (3)C18—C191.392 (3)
C4—C51.394 (3)C19—C201.382 (3)
C4—H40.93C19—H190.93
C5—C61.407 (3)C20—C211.367 (4)
C5—C171.490 (3)C20—H200.93
C6—C241.511 (3)C21—C221.371 (4)
C7—C81.327 (3)C21—H210.93
C7—H70.93C22—C231.385 (3)
C8—H80.93C22—H220.93
C9—H9A0.96C23—H230.93
C9—H9B0.96C24—H24A0.96
C9—H9C0.96C24—H24B0.96
C10—C111.500 (3)C24—H24C0.96
C11—C161.373 (4)
C10—N1—C3121.26 (17)C13—C12—H12120
C10—N1—H2123.4C11—C12—H12120
C3—N1—H2114.5C14—C13—C12120.0 (3)
C8—O1—C9116.0 (2)C14—C13—H13120
C6—C1—C2123.29 (19)C12—C13—H13120
C6—C1—H1118.4C15—C14—C13120.1 (3)
C2—C1—H1118.4C15—C14—H14120
C3—C2—C1116.84 (18)C13—C14—H14120
C3—C2—C7120.59 (18)C14—C15—C16120.1 (3)
C1—C2—C7122.53 (19)C14—C15—H15120
C4—C3—C2120.89 (17)C16—C15—H15120
C4—C3—N1118.35 (18)C11—C16—C15120.6 (3)
C2—C3—N1120.75 (18)C11—C16—H16119.7
C3—C4—C5121.58 (18)C15—C16—H16119.7
C3—C4—H4119.2O2—C17—C5121.63 (19)
C5—C4—H4119.2O2—C17—C18119.83 (19)
C4—C5—C6118.98 (19)C5—C17—C18118.53 (18)
C4—C5—C17118.09 (18)C23—C18—C19118.9 (2)
C6—C5—C17122.89 (17)C23—C18—C17119.2 (2)
C1—C6—C5118.42 (18)C19—C18—C17121.9 (2)
C1—C6—C24118.45 (19)C20—C19—C18120.5 (2)
C5—C6—C24123.07 (19)C20—C19—H19119.8
C8—C7—C2129.5 (2)C18—C19—H19119.8
C8—C7—H7115.3C21—C20—C19120.0 (3)
C2—C7—H7115.3C21—C20—H20120
C7—C8—O1124.2 (2)C19—C20—H20120
C7—C8—H8117.9C20—C21—C22120.2 (2)
O1—C8—H8117.9C20—C21—H21119.9
O1—C9—H9A109.5C22—C21—H21119.9
O1—C9—H9B109.5C21—C22—C23120.4 (3)
H9A—C9—H9B109.5C21—C22—H22119.8
O1—C9—H9C109.5C23—C22—H22119.8
H9A—C9—H9C109.5C18—C23—C22120.0 (2)
H9B—C9—H9C109.5C18—C23—H23120
O3—C10—N1121.88 (19)C22—C23—H23120
O3—C10—C11121.6 (2)C6—C24—H24A109.5
N1—C10—C11116.48 (19)C6—C24—H24B109.5
C16—C11—C12119.1 (2)H24A—C24—H24B109.5
C16—C11—C10123.7 (2)C6—C24—H24C109.5
C12—C11—C10117.2 (2)H24A—C24—H24C109.5
C13—C12—C11120.1 (3)H24B—C24—H24C109.5
C6—C1—C2—C30.1 (3)O3—C10—C11—C1225.1 (4)
C6—C1—C2—C7177.7 (2)N1—C10—C11—C12154.1 (2)
C1—C2—C3—C40.0 (3)C16—C11—C12—C130.8 (4)
C7—C2—C3—C4177.9 (2)C10—C11—C12—C13178.4 (2)
C1—C2—C3—N1178.95 (19)C11—C12—C13—C141.1 (5)
C7—C2—C3—N11.1 (3)C12—C13—C14—C151.0 (5)
C10—N1—C3—C470.6 (3)C13—C14—C15—C160.6 (5)
C10—N1—C3—C2108.4 (2)C12—C11—C16—C150.3 (4)
C2—C3—C4—C50.2 (3)C10—C11—C16—C15178.8 (3)
N1—C3—C4—C5179.14 (19)C14—C15—C16—C110.2 (5)
C3—C4—C5—C60.4 (3)C4—C5—C17—O2140.2 (2)
C3—C4—C5—C17177.39 (19)C6—C5—C17—O237.5 (3)
C2—C1—C6—C50.3 (3)C4—C5—C17—C1838.7 (3)
C2—C1—C6—C24176.9 (2)C6—C5—C17—C18143.6 (2)
C4—C5—C6—C10.5 (3)O2—C17—C18—C2328.3 (3)
C17—C5—C6—C1177.2 (2)C5—C17—C18—C23150.6 (2)
C4—C5—C6—C24176.6 (2)O2—C17—C18—C19148.4 (2)
C17—C5—C6—C245.7 (3)C5—C17—C18—C1932.6 (3)
C3—C2—C7—C8164.7 (2)C23—C18—C19—C200.6 (3)
C1—C2—C7—C817.6 (4)C17—C18—C19—C20176.1 (2)
C2—C7—C8—O10.4 (4)C18—C19—C20—C211.6 (4)
C9—O1—C8—C7178.1 (3)C19—C20—C21—C220.6 (4)
C3—N1—C10—O31.4 (4)C20—C21—C22—C231.3 (4)
C3—N1—C10—C11177.8 (2)C19—C18—C23—C221.3 (3)
O3—C10—C11—C16155.8 (3)C17—C18—C23—C22178.1 (2)
N1—C10—C11—C1625.0 (3)C21—C22—C23—C182.2 (4)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H2···O2i0.822.273.021 (2)153
C14—H14···Cg3ii0.932.993.820 (4)150
Symmetry codes: (i) x, y+1, z+1; (ii) x, y+1, z.
 

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