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The title compound, C16H20BrNO4, displays almost planar coordination at the en­amine N atom, which thus has a stereochemically inactive lone pair. There is no indication of delocalized charge within the dide­hydrogenated amino acid, as shown by the bond lengths. The mol­ecules are linked in pairs by two hydrogen bonds (N—H...O and C—H...O), and then by a longer C—H...O contact to form columns parallel to the a axis.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S160053680300357X/bt6240sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S160053680300357X/bt6240Isup2.hkl
Contains datablock I

CCDC reference: 206796

Key indicators

  • Single-crystal X-ray study
  • T = 173 K
  • Mean [sigma](C-C) = 0.005 Å
  • R factor = 0.034
  • wR factor = 0.050
  • Data-to-parameter ratio = 14.7

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry


Yellow Alert Alert Level C:
GOODF_01 Alert C The least squares goodness of fit parameter lies outside the range 0.80 <> 2.00 Goodness of fit given = 0.792 General Notes
ABSTM_02 When printed, the submitted absorption T values will be replaced by the scaled T values. Since the ratio of scaled T's is identical to the ratio of reported T values, the scaling does not imply a change to the absorption corrections used in the study. Ratio of Tmax expected/reported 0.707 Tmax scaled 0.623 Tmin scaled 0.561
0 Alert Level A = Potentially serious problem
0 Alert Level B = Potential problem
1 Alert Level C = Please check

Computing details top

Data collection: XSCANS (Fait, 1991); cell refinement: XSCANS; data reduction: XSCANS; program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: XP (Siemens, 1994); software used to prepare material for publication: SHELXL7.

Ethyl (Z)-3-bromo-2-[(tert-butoxycarbonyl)amino]-3-phenylacrylate top
Crystal data top
C16H20BrNO4F(000) = 380
Mr = 370.24Dx = 1.407 Mg m3
Triclinic, P1Melting point: 377 K
a = 8.5554 (12) ÅMo Kα radiation, λ = 0.71073 Å
b = 10.1468 (18) ÅCell parameters from 62 reflections
c = 10.7086 (16) Åθ = 2–11°
α = 71.729 (10)°µ = 2.37 mm1
β = 87.445 (10)°T = 173 K
γ = 81.861 (10)°Prism, colourless
V = 873.9 (2) Å30.26 × 0.20 × 0.20 mm
Z = 2
Data collection top
Siemens P4
diffractometer
2016 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.046
Graphite monochromatorθmax = 25.0°, θmin = 3.1°
ω scansh = 1010
Absorption correction: ψ scan
(XEMP; Siemens, 1990)
k = 1111
Tmin = 0.793, Tmax = 0.881l = 1212
6090 measured reflections3 standard reflections every 247 reflections
3046 independent reflections intensity decay: none
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)] = 0.034Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.050H atoms treated by a mixture of independent and constrained refinement
S = 0.79 w = 1/[σ2(Fo2) + (0.0143P)2]
where P = (Fo2 + 2Fc2)/3
3046 reflections(Δ/σ)max = 0.009
207 parametersΔρmax = 0.26 e Å3
0 restraintsΔρmin = 0.26 e Å3
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
Br10.60956 (4)0.24747 (4)0.34421 (3)0.03920 (12)
C10.4143 (3)0.2765 (3)0.2518 (3)0.0253 (7)
C20.4194 (3)0.3118 (3)0.1222 (3)0.0224 (7)
C30.2699 (3)0.3404 (3)0.0425 (3)0.0237 (7)
O10.2361 (2)0.44328 (19)0.04988 (17)0.0281 (5)
O20.1833 (2)0.23671 (19)0.08961 (17)0.0287 (5)
C40.0264 (3)0.2568 (3)0.0345 (3)0.0349 (8)
H4A0.03280.26330.05980.042*
H4B0.03580.34350.04320.042*
C50.0475 (4)0.1317 (3)0.1116 (3)0.0633 (11)
H5A0.01580.04690.10220.076*
H5B0.15450.13910.07880.076*
H5C0.05230.12660.20460.076*
N10.5568 (3)0.3381 (2)0.0476 (2)0.0241 (6)
H10.618 (3)0.391 (3)0.067 (2)0.027 (9)*
C60.5931 (4)0.3062 (3)0.0666 (3)0.0251 (7)
O30.7026 (2)0.3463 (2)0.13632 (19)0.0383 (6)
O40.4932 (2)0.22325 (19)0.08471 (16)0.0269 (5)
C70.4880 (4)0.1960 (3)0.2127 (3)0.0333 (8)
C80.3574 (4)0.1056 (3)0.1902 (3)0.0522 (10)
H8A0.38360.02200.11430.063*
H8B0.34570.07730.26840.063*
H8C0.25820.15860.17340.063*
C90.4454 (4)0.3347 (3)0.3199 (3)0.0521 (10)
H9A0.35170.38710.29330.063*
H9B0.42320.31700.40170.063*
H9C0.53390.38940.33370.063*
C100.6438 (4)0.1167 (3)0.2380 (3)0.0514 (10)
H10A0.72710.17680.25080.062*
H10B0.63480.08930.31710.062*
H10C0.67030.03270.16260.062*
C110.2712 (3)0.2689 (3)0.3362 (3)0.0288 (8)
C120.2548 (4)0.1486 (3)0.4391 (3)0.0363 (8)
H120.33770.07220.45900.044*
C130.1172 (4)0.1395 (4)0.5133 (3)0.0508 (10)
H130.10580.05630.58320.061*
C140.0028 (4)0.2499 (4)0.4865 (3)0.0539 (10)
H140.09660.24330.53780.065*
C150.0140 (4)0.3698 (4)0.3850 (3)0.0575 (11)
H150.06910.44600.36570.069*
C160.1512 (4)0.3804 (3)0.3105 (3)0.0419 (9)
H160.16260.46440.24170.050*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Br10.0361 (2)0.0507 (2)0.02955 (18)0.00202 (17)0.00921 (14)0.01111 (16)
C10.0281 (18)0.0250 (18)0.0237 (16)0.0020 (15)0.0052 (14)0.0089 (14)
C20.0244 (17)0.0178 (18)0.0259 (17)0.0035 (14)0.0008 (14)0.0077 (13)
C30.0227 (17)0.026 (2)0.0226 (17)0.0007 (15)0.0000 (14)0.0093 (15)
O10.0275 (12)0.0254 (13)0.0284 (11)0.0050 (10)0.0025 (9)0.0029 (10)
O20.0233 (12)0.0282 (13)0.0320 (12)0.0079 (10)0.0027 (9)0.0035 (10)
C40.0243 (18)0.033 (2)0.046 (2)0.0070 (16)0.0029 (15)0.0084 (17)
C50.029 (2)0.049 (3)0.096 (3)0.0113 (19)0.007 (2)0.004 (2)
N10.0238 (15)0.0259 (16)0.0272 (14)0.0079 (13)0.0000 (12)0.0127 (12)
C60.0267 (19)0.0207 (19)0.0265 (18)0.0013 (15)0.0029 (15)0.0069 (15)
O30.0360 (14)0.0500 (16)0.0329 (13)0.0192 (12)0.0143 (11)0.0146 (11)
O40.0304 (12)0.0293 (13)0.0258 (11)0.0084 (10)0.0024 (9)0.0137 (10)
C70.048 (2)0.033 (2)0.0243 (18)0.0072 (18)0.0021 (16)0.0162 (16)
C80.065 (3)0.059 (3)0.047 (2)0.023 (2)0.0029 (19)0.0308 (19)
C90.077 (3)0.045 (2)0.0314 (19)0.005 (2)0.0121 (18)0.0124 (18)
C100.068 (3)0.047 (2)0.043 (2)0.002 (2)0.0086 (19)0.0250 (19)
C110.033 (2)0.033 (2)0.0219 (17)0.0098 (17)0.0016 (15)0.0092 (15)
C120.048 (2)0.034 (2)0.0266 (18)0.0097 (17)0.0085 (16)0.0050 (16)
C130.061 (3)0.063 (3)0.027 (2)0.034 (2)0.0023 (19)0.0010 (19)
C140.044 (2)0.082 (3)0.039 (2)0.022 (2)0.0189 (18)0.019 (2)
C150.040 (2)0.065 (3)0.063 (3)0.002 (2)0.017 (2)0.018 (2)
C160.039 (2)0.036 (2)0.044 (2)0.0059 (18)0.0126 (17)0.0047 (17)
Geometric parameters (Å, º) top
Br1—C11.918 (3)C7—C91.519 (4)
C1—C21.321 (3)C8—H8A0.9800
C1—C111.485 (4)C8—H8B0.9800
C2—N11.401 (3)C8—H8C0.9800
C2—C31.512 (4)C9—H9A0.9800
C3—O11.202 (3)C9—H9B0.9800
C3—O21.329 (3)C9—H9C0.9800
O2—C41.453 (3)C10—H10A0.9800
C4—C51.488 (4)C10—H10B0.9800
C4—H4A0.9900C10—H10C0.9800
C4—H4B0.9900C11—C161.382 (4)
C5—H5A0.9800C11—C121.385 (4)
C5—H5B0.9800C12—C131.388 (4)
C5—H5C0.9800C12—H120.9500
N1—C61.372 (3)C13—C141.374 (4)
N1—H10.87 (2)C13—H130.9500
C6—O31.206 (3)C14—C151.374 (4)
C6—O41.341 (3)C14—H140.9500
O4—C71.484 (3)C15—C161.387 (4)
C7—C81.508 (4)C15—H150.9500
C7—C101.517 (4)C16—H160.9500
C2—C1—C11127.2 (3)C7—C8—H8B109.5
C2—C1—Br1117.9 (2)H8A—C8—H8B109.5
C11—C1—Br1114.69 (18)C7—C8—H8C109.5
C1—C2—N1124.1 (3)H8A—C8—H8C109.5
C1—C2—C3120.9 (3)H8B—C8—H8C109.5
N1—C2—C3114.8 (2)C7—C9—H9A109.5
O1—C3—O2125.7 (3)C7—C9—H9B109.5
O1—C3—C2123.9 (3)H9A—C9—H9B109.5
O2—C3—C2110.4 (2)C7—C9—H9C109.5
C3—O2—C4117.1 (2)H9A—C9—H9C109.5
O2—C4—C5105.6 (2)H9B—C9—H9C109.5
O2—C4—H4A110.6C7—C10—H10A109.5
C5—C4—H4A110.6C7—C10—H10B109.5
O2—C4—H4B110.6H10A—C10—H10B109.5
C5—C4—H4B110.6C7—C10—H10C109.5
H4A—C4—H4B108.8H10A—C10—H10C109.5
C4—C5—H5A109.5H10B—C10—H10C109.5
C4—C5—H5B109.5C16—C11—C12119.3 (3)
H5A—C5—H5B109.5C16—C11—C1120.4 (3)
C4—C5—H5C109.5C12—C11—C1120.3 (3)
H5A—C5—H5C109.5C11—C12—C13120.0 (3)
H5B—C5—H5C109.5C11—C12—H12120.0
C6—N1—C2125.6 (3)C13—C12—H12120.0
C6—N1—H1115.8 (17)C14—C13—C12120.6 (3)
C2—N1—H1117.9 (17)C14—C13—H13119.7
O3—C6—O4126.7 (3)C12—C13—H13119.7
O3—C6—N1123.2 (3)C15—C14—C13119.5 (3)
O4—C6—N1110.1 (3)C15—C14—H14120.3
C6—O4—C7120.4 (2)C13—C14—H14120.3
O4—C7—C8102.0 (2)C14—C15—C16120.5 (3)
O4—C7—C10110.2 (2)C14—C15—H15119.7
C8—C7—C10110.9 (3)C16—C15—H15119.7
O4—C7—C9108.8 (2)C11—C16—C15120.1 (3)
C8—C7—C9111.7 (3)C11—C16—H16119.9
C10—C7—C9112.8 (3)C15—C16—H16119.9
C7—C8—H8A109.5
C11—C1—C2—N1169.6 (3)N1—C6—O4—C7168.3 (2)
Br1—C1—C2—N14.3 (4)C6—O4—C7—C8177.6 (2)
C11—C1—C2—C34.4 (4)C6—O4—C7—C1064.6 (3)
Br1—C1—C2—C3178.3 (2)C6—O4—C7—C959.5 (3)
C1—C2—C3—O1129.7 (3)C2—C1—C11—C1650.8 (4)
N1—C2—C3—O144.8 (4)Br1—C1—C11—C16123.3 (3)
C1—C2—C3—O250.1 (4)C2—C1—C11—C12127.4 (3)
N1—C2—C3—O2135.3 (2)Br1—C1—C11—C1258.5 (3)
O1—C3—O2—C47.6 (4)C16—C11—C12—C131.5 (4)
C2—C3—O2—C4172.3 (2)C1—C11—C12—C13176.7 (3)
C3—O2—C4—C5175.5 (2)C11—C12—C13—C140.8 (5)
C1—C2—N1—C6145.0 (3)C12—C13—C14—C150.3 (5)
C3—C2—N1—C640.7 (4)C13—C14—C15—C160.5 (5)
C2—N1—C6—O3170.3 (3)C12—C11—C16—C151.8 (5)
C2—N1—C6—O411.3 (4)C1—C11—C16—C15176.4 (3)
O3—C6—O4—C713.4 (4)C14—C15—C16—C111.3 (5)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1···O1i0.87 (2)2.19 (3)3.035 (3)162 (2)
C4—H4B···O1ii0.992.583.561 (4)170
C16—H16···O3i0.952.333.204 (4)152
Symmetry codes: (i) x+1, y+1, z; (ii) x, y+1, z.
 

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