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The title compound, C17H17NO4, was synthesized by the Reformatsky reaction of 1,3-benzodioxole-5-carbaldehyde and N-methyl-N-phenyl­carbamic bromide. The two benzene rings are inclined at a dihedral angle of 50.6 (3)°.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806047039/rn2019sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806047039/rn2019Isup2.hkl
Contains datablock I

CCDC reference: 630218

Key indicators

  • Single-crystal X-ray study
  • T = 294 K
  • Mean [sigma](C-C) = 0.003 Å
  • R factor = 0.043
  • wR factor = 0.132
  • Data-to-parameter ratio = 15.2

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT152_ALERT_1_C Supplied and Calc Volume s.u. Inconsistent ..... ?
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 1 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 0 ALERT type 2 Indicator that the structure model may be wrong or deficient 0 ALERT type 3 Indicator that the structure quality may be low 0 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check

Computing details top

Data collection: SMART (Bruker, 1997); cell refinement: SAINT (Bruker, 1997); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1997); software used to prepare material for publication: SHELXTL.

3-(1,3-Benzodioxol-5-yl)-3-hydroxy-N-methyl-N-phenylpropionamide top
Crystal data top
C17H17NO4F(000) = 632
Mr = 299.32Dx = 1.341 Mg m3
Monoclinic, P21/cMelting point: 158 K
Hall symbol: -P2ybcMo Kα radiation, λ = 0.71073 Å
a = 15.864 (5) ÅCell parameters from 1769 reflections
b = 11.590 (4) Åθ = 3.1–23.0°
c = 8.356 (3) ŵ = 0.10 mm1
β = 105.183 (6)°T = 294 K
V = 1482.9 (8) Å3Block, colorless
Z = 40.22 × 0.18 × 0.12 mm
Data collection top
Bruker SMART CCD area-detector
diffractometer
3038 independent reflections
Radiation source: fine-focus sealed tube1648 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.042
φ and ω scansθmax = 26.4°, θmin = 1.3°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 1219
Tmin = 0.963, Tmax = 0.989k = 1314
8186 measured reflectionsl = 1010
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)] = 0.043Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.132H-atom parameters constrained
S = 1.00 w = 1/[σ2(Fo2) + (0.0596P)2 + 0.1641P]
where P = (Fo2 + 2Fc2)/3
3038 reflections(Δ/σ)max = 0.002
200 parametersΔρmax = 0.30 e Å3
0 restraintsΔρmin = 0.19 e Å3
Special details top

Experimental. IR (KBr, ν cm-1): 3389, 1629; 1H NMR (CDCl3): δ 7.41–6.69 (m, 8H), 5.89 (s, 2H), 4.99 (t, 1H), 4.72 (s, 1H), 3.27 (s, 3H), 2.38 (d, 2H).

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
O11.05893 (10)0.62061 (16)0.7320 (2)0.0635 (5)
O20.95852 (10)0.48568 (14)0.7645 (2)0.0612 (5)
O30.65580 (10)0.60293 (13)0.3927 (2)0.0594 (5)
H30.63330.65230.43830.089*
O40.59080 (10)0.70204 (13)0.0201 (2)0.0561 (5)
N10.60693 (11)0.53002 (16)0.0927 (2)0.0485 (5)
C11.04957 (15)0.5108 (2)0.8006 (3)0.0609 (7)
H1A1.07490.51180.91960.073*
H1B1.07930.45240.75250.073*
C20.97936 (14)0.64156 (19)0.6209 (3)0.0467 (6)
C30.92008 (14)0.56078 (17)0.6392 (3)0.0412 (5)
C40.83463 (13)0.56334 (17)0.5482 (3)0.0407 (5)
H40.79500.50770.56270.049*
C50.80889 (13)0.65260 (17)0.4328 (3)0.0389 (5)
C60.87026 (16)0.73405 (19)0.4179 (3)0.0531 (6)
H60.85290.79360.34180.064*
C70.95679 (16)0.7307 (2)0.5115 (3)0.0575 (7)
H70.99710.78630.50020.069*
C80.71767 (13)0.65579 (18)0.3193 (3)0.0427 (5)
H80.70070.73620.29250.051*
C90.71485 (14)0.59071 (19)0.1601 (3)0.0468 (6)
H9A0.76470.61350.12060.056*
H9B0.72000.50870.18410.056*
C100.63231 (13)0.61186 (19)0.0243 (3)0.0422 (5)
C110.52996 (16)0.5509 (2)0.2313 (3)0.0755 (8)
H11A0.49520.61100.20190.113*
H11B0.49600.48150.25530.113*
H11C0.54830.57380.32730.113*
C120.65673 (14)0.42742 (18)0.1004 (3)0.0423 (5)
C130.73507 (15)0.4351 (2)0.1425 (3)0.0501 (6)
H130.75580.50690.16430.060*
C140.78245 (15)0.3378 (2)0.1525 (3)0.0552 (6)
H140.83530.34380.18030.066*
C150.75204 (17)0.2317 (2)0.1216 (3)0.0575 (7)
H150.78450.16570.12700.069*
C160.67368 (17)0.2231 (2)0.0827 (3)0.0620 (7)
H160.65280.15090.06330.074*
C170.62518 (15)0.3208 (2)0.0718 (3)0.0556 (6)
H170.57190.31450.04550.067*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0469 (10)0.0769 (12)0.0626 (12)0.0108 (9)0.0070 (9)0.0025 (10)
O20.0511 (11)0.0696 (11)0.0591 (11)0.0018 (8)0.0080 (8)0.0172 (9)
O30.0541 (10)0.0553 (10)0.0749 (13)0.0066 (8)0.0275 (9)0.0029 (9)
O40.0470 (9)0.0508 (10)0.0706 (12)0.0127 (8)0.0157 (8)0.0100 (8)
N10.0400 (11)0.0540 (12)0.0464 (12)0.0030 (9)0.0021 (9)0.0004 (10)
C10.0487 (16)0.0716 (18)0.0590 (17)0.0042 (13)0.0081 (12)0.0005 (14)
C20.0416 (13)0.0534 (14)0.0458 (14)0.0092 (11)0.0125 (11)0.0095 (12)
C30.0476 (13)0.0392 (12)0.0392 (13)0.0042 (10)0.0160 (11)0.0021 (10)
C40.0450 (13)0.0366 (12)0.0438 (14)0.0097 (10)0.0176 (11)0.0044 (10)
C50.0452 (12)0.0325 (11)0.0412 (13)0.0029 (10)0.0152 (10)0.0058 (10)
C60.0608 (16)0.0422 (13)0.0572 (16)0.0107 (11)0.0169 (13)0.0061 (11)
C70.0562 (16)0.0520 (15)0.0656 (18)0.0221 (12)0.0180 (13)0.0026 (13)
C80.0449 (13)0.0346 (11)0.0506 (14)0.0001 (10)0.0163 (11)0.0002 (10)
C90.0448 (13)0.0463 (13)0.0474 (14)0.0072 (10)0.0086 (11)0.0052 (11)
C100.0365 (12)0.0435 (13)0.0492 (14)0.0010 (11)0.0155 (10)0.0068 (11)
C110.0525 (16)0.096 (2)0.0635 (19)0.0126 (14)0.0111 (13)0.0021 (16)
C120.0396 (12)0.0487 (13)0.0356 (13)0.0059 (11)0.0044 (10)0.0028 (10)
C130.0528 (14)0.0495 (14)0.0502 (15)0.0084 (11)0.0173 (12)0.0013 (11)
C140.0535 (15)0.0566 (15)0.0591 (16)0.0022 (12)0.0213 (12)0.0057 (13)
C150.0579 (16)0.0496 (15)0.0602 (18)0.0027 (12)0.0071 (13)0.0058 (12)
C160.0688 (18)0.0464 (15)0.0672 (19)0.0139 (13)0.0116 (14)0.0006 (13)
C170.0449 (14)0.0603 (16)0.0614 (16)0.0139 (12)0.0135 (12)0.0049 (13)
Geometric parameters (Å, º) top
O1—C21.379 (3)C7—H70.9300
O1—C11.419 (3)C8—C91.520 (3)
O2—C31.376 (3)C8—H80.9800
O2—C11.426 (3)C9—C101.511 (3)
O3—C81.425 (2)C9—H9A0.9700
O3—H30.8200C9—H9B0.9700
O4—C101.231 (2)C11—H11A0.9600
N1—C101.346 (3)C11—H11B0.9600
N1—C121.438 (3)C11—H11C0.9600
N1—C111.466 (3)C12—C171.377 (3)
C1—H1A0.9700C12—C131.381 (3)
C1—H1B0.9700C13—C141.370 (3)
C2—C31.364 (3)C13—H130.9300
C2—C71.364 (3)C14—C151.370 (3)
C3—C41.370 (3)C14—H140.9300
C4—C51.400 (3)C15—C161.369 (3)
C4—H40.9300C15—H150.9300
C5—C61.385 (3)C16—C171.385 (3)
C5—C81.509 (3)C16—H160.9300
C6—C71.391 (3)C17—H170.9300
C6—H60.9300
C2—O1—C1104.81 (17)C9—C8—H8109.2
C3—O2—C1104.73 (17)C10—C9—C8113.44 (18)
C8—O3—H3109.5C10—C9—H9A108.9
C10—N1—C12123.49 (17)C8—C9—H9A108.9
C10—N1—C11119.11 (19)C10—C9—H9B108.9
C12—N1—C11117.02 (19)C8—C9—H9B108.9
O1—C1—O2107.76 (18)H9A—C9—H9B107.7
O1—C1—H1A110.2O4—C10—N1121.4 (2)
O2—C1—H1A110.2O4—C10—C9120.7 (2)
O1—C1—H1B110.2N1—C10—C9117.81 (19)
O2—C1—H1B110.2N1—C11—H11A109.5
H1A—C1—H1B108.5N1—C11—H11B109.5
C3—C2—C7121.8 (2)H11A—C11—H11B109.5
C3—C2—O1109.9 (2)N1—C11—H11C109.5
C7—C2—O1128.2 (2)H11A—C11—H11C109.5
C2—C3—C4122.3 (2)H11B—C11—H11C109.5
C2—C3—O2109.78 (19)C17—C12—C13119.6 (2)
C4—C3—O2127.81 (19)C17—C12—N1120.3 (2)
C3—C4—C5117.76 (19)C13—C12—N1119.97 (19)
C3—C4—H4121.1C14—C13—C12120.5 (2)
C5—C4—H4121.1C14—C13—H13119.8
C6—C5—C4118.7 (2)C12—C13—H13119.8
C6—C5—C8120.5 (2)C13—C14—C15120.1 (2)
C4—C5—C8120.65 (18)C13—C14—H14119.9
C5—C6—C7122.9 (2)C15—C14—H14119.9
C5—C6—H6118.5C16—C15—C14119.8 (2)
C7—C6—H6118.5C16—C15—H15120.1
C2—C7—C6116.5 (2)C14—C15—H15120.1
C2—C7—H7121.8C15—C16—C17120.7 (2)
C6—C7—H7121.8C15—C16—H16119.6
O3—C8—C5111.97 (18)C17—C16—H16119.6
O3—C8—C9107.33 (17)C12—C17—C16119.3 (2)
C5—C8—C9109.97 (17)C12—C17—H17120.4
O3—C8—H8109.2C16—C17—H17120.4
C5—C8—H8109.2
C2—O1—C1—O216.6 (2)C4—C5—C8—C989.9 (2)
C3—O2—C1—O117.2 (2)O3—C8—C9—C1071.0 (2)
C1—O1—C2—C39.7 (2)C5—C8—C9—C10166.92 (18)
C1—O1—C2—C7173.5 (2)C12—N1—C10—O4175.03 (19)
C7—C2—C3—C40.6 (3)C11—N1—C10—O42.3 (3)
O1—C2—C3—C4177.62 (19)C12—N1—C10—C93.8 (3)
C7—C2—C3—O2176.0 (2)C11—N1—C10—C9176.5 (2)
O1—C2—C3—O21.0 (2)C8—C9—C10—O426.3 (3)
C1—O2—C3—C211.2 (2)C8—C9—C10—N1154.86 (18)
C1—O2—C3—C4172.4 (2)C10—N1—C12—C17113.0 (2)
C2—C3—C4—C50.3 (3)C11—N1—C12—C1774.1 (3)
O2—C3—C4—C5176.20 (19)C10—N1—C12—C1369.4 (3)
C3—C4—C5—C60.8 (3)C11—N1—C12—C13103.5 (3)
C3—C4—C5—C8175.33 (18)C17—C12—C13—C141.5 (3)
C4—C5—C6—C70.6 (3)N1—C12—C13—C14179.1 (2)
C8—C5—C6—C7175.6 (2)C12—C13—C14—C150.4 (4)
C3—C2—C7—C60.8 (4)C13—C14—C15—C160.8 (4)
O1—C2—C7—C6177.3 (2)C14—C15—C16—C170.9 (4)
C5—C6—C7—C20.2 (4)C13—C12—C17—C161.3 (3)
C6—C5—C8—O3154.59 (19)N1—C12—C17—C16178.9 (2)
C4—C5—C8—O329.3 (3)C15—C16—C17—C120.1 (4)
C6—C5—C8—C986.2 (2)
 

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