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In the title adduct, C4H4O4·2C9H9NO, fumaric acid has a centre of symmetry and is connected to two trans-cinnam­amide mol­ecules through cyclic hydrogen bonds. A single-crystal photoirradiation promoted the conformational disorder of the fumaric acid.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270100013007/qa0399sup1.cif
Contains datablocks global, I, I'

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108270100013007/qa0399Isup2.hkl
Contains datablock I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108270100013007/qa0399I'sup3.hkl
Contains datablock I'

CCDC references: 153936; 153937

Computing details top

For both compounds, 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). Molecular graphics: ORTEP-II (Johnson, 1976) for I'. For both compounds, software used to prepare material for publication: TEXSAN.

(I) top
Crystal data top
C4H4O4·2C9H9NODx = 1.328 Mg m3
Mr = 410.43Mo Kα radiation, λ = 0.71073 Å
Monoclinic, P21/nCell parameters from 25 reflections
a = 11.505 (2) Åθ = 13.3–14.9°
b = 5.298 (1) ŵ = 0.10 mm1
c = 16.886 (2) ÅT = 298 K
β = 94.057 (9)°Prism, colourless
V = 1026.6 (3) Å30.7 × 0.6 × 0.25 mm
Z = 2
Data collection top
Rigaku AFC-7R
diffractometer
θmax = 27.5°, θmin = 2.5°
θ–2θ scansh = 015
2462 measured reflectionsk = 70
2351 independent reflectionsl = 2222
1873 reflections with I > 2σ(I)3 standard reflections every 150 reflections
Rint = 0.007 intensity decay: none
Refinement top
Refinement on F2 w = 1/[σ2(Fo2) + (0.0438P)2 + 0.2732P]
where P = (Fo2 + 2Fc2)/3
R[F2 > 2σ(F2)] = 0.038(Δ/σ)max = 0.001
wR(F2) = 0.107Δρmax = 0.17 e Å3
S = 1.06Δρmin = 0.15 e Å3
2351 reflectionsExtinction correction: SHELXL97 (Sheldrick, 1997), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
194 parametersExtinction coefficient: 0.016 (2)
H atoms: see text
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*/UeqOcc. (<1)
O10.37287 (9)0.1242 (2)0.19944 (7)0.0617 (3)
O20.3880 (1)0.8094 (3)0.4052 (1)0.0577 (4)0.921 (3)
O2*0.387 (2)0.890 (4)0.396 (1)0.0577*0.079 (3)
O30.2920 (1)0.4466 (3)0.3935 (1)0.0616 (4)0.921 (3)
O3*0.313 (2)0.504 (4)0.418 (1)0.0615*0.079 (3)
N40.3520 (1)0.5418 (3)0.1838 (1)0.0636 (4)
C50.3787 (1)0.5894 (4)0.42138 (9)0.0405 (4)0.921 (3)
C5*0.385 (2)0.694 (5)0.433 (1)0.0405*0.079 (3)
C60.4617 (1)0.4436 (3)0.47534 (9)0.0401 (4)0.921 (3)
C6*0.484 (1)0.612 (4)0.4887 (10)0.0401*0.079 (3)
C70.4100 (1)0.3411 (3)0.21127 (9)0.0454 (3)
C80.5227 (1)0.3861 (3)0.25671 (9)0.0463 (3)
C90.5715 (1)0.2074 (3)0.30237 (8)0.0427 (3)
C100.6817 (1)0.2190 (3)0.35144 (8)0.0400 (3)
C110.7054 (1)0.0326 (3)0.4079 (1)0.0552 (4)
C120.8072 (2)0.0384 (4)0.4572 (1)0.0657 (5)
C130.8867 (2)0.2263 (4)0.4489 (1)0.0665 (5)
C140.8662 (1)0.4099 (4)0.3921 (1)0.0651 (5)
C150.7637 (1)0.4076 (3)0.34362 (9)0.0524 (4)
H30.239 (2)0.539 (5)0.362 (1)0.09349 (9)*0.921 (3)
H4A0.282 (2)0.518 (4)0.160 (1)0.08221 (8)*
H4B0.375 (2)0.698 (5)0.195 (1)0.09092 (9)*
H60.458 (1)0.262 (3)0.4740 (10)0.04677 (6)*0.921 (3)
H80.555 (1)0.549 (4)0.252 (1)0.06350 (6)*
H90.529 (1)0.055 (3)0.3040 (10)0.05878 (6)*
H110.649 (2)0.100 (4)0.412 (1)0.07252 (7)*
H120.818 (2)0.094 (4)0.496 (1)0.08459 (8)*
H130.957 (2)0.232 (4)0.485 (1)0.09171 (8)*
H140.921 (2)0.542 (4)0.385 (1)0.08002 (7)*
H150.750 (1)0.539 (3)0.304 (1)0.06406 (6)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0488 (6)0.0455 (6)0.0863 (8)0.0004 (5)0.0277 (5)0.0001 (5)
O20.0542 (7)0.0440 (9)0.0715 (9)0.0091 (7)0.0198 (6)0.0123 (8)
O30.0532 (7)0.0426 (7)0.083 (1)0.0047 (5)0.0342 (7)0.0049 (6)
N40.0531 (8)0.0480 (8)0.086 (1)0.0080 (6)0.0236 (7)0.0032 (7)
C50.0357 (7)0.0394 (8)0.0451 (8)0.0001 (7)0.0064 (6)0.0008 (7)
C60.0364 (7)0.0361 (8)0.0469 (8)0.0018 (6)0.0043 (6)0.0016 (6)
C70.0395 (7)0.0426 (7)0.0526 (8)0.0032 (6)0.0069 (6)0.0002 (6)
C80.0398 (7)0.0409 (7)0.0565 (8)0.0015 (6)0.0081 (6)0.0003 (6)
C90.0362 (6)0.0408 (7)0.0505 (7)0.0014 (5)0.0022 (5)0.0006 (6)
C100.0353 (6)0.0421 (7)0.0419 (6)0.0035 (5)0.0015 (5)0.0014 (5)
C110.0488 (8)0.0539 (9)0.0616 (9)0.0003 (7)0.0050 (7)0.0122 (7)
C120.0613 (10)0.072 (1)0.0617 (10)0.0106 (9)0.0140 (8)0.0167 (9)
C130.0498 (9)0.078 (1)0.069 (1)0.0080 (8)0.0214 (8)0.0048 (9)
C140.0454 (8)0.070 (1)0.077 (1)0.0126 (8)0.0133 (8)0.0019 (9)
C150.0451 (8)0.0535 (9)0.0572 (9)0.0056 (6)0.0067 (6)0.0093 (7)
Geometric parameters (Å, º) top
O1—C71.237 (2)C8—C91.321 (2)
O2—C51.203 (3)C8—H80.94 (2)
O2*—C5*1.21 (3)C9—C101.465 (2)
O3—C51.312 (2)C9—H90.94 (2)
O3—H30.923 (2)C10—C111.387 (2)
O3*—C5*1.32 (3)C10—C151.387 (2)
N4—C71.322 (2)C11—C121.388 (2)
N4—H4A0.88 (2)C11—H110.96 (2)
N4—H4B0.89 (2)C12—C131.367 (3)
C5—C61.489 (2)C12—H120.96 (2)
C5*—C6*1.50 (2)C13—C141.374 (3)
C6—C6i1.314 (3)C13—H130.97 (2)
C6—H60.96 (2)C14—C151.388 (2)
C6*—C6*i1.29 (4)C14—H140.96 (2)
C7—C81.479 (2)C15—H150.97 (2)
C5—O3—H3110 (1)C8—C9—H9115.5 (10)
C7—N4—H4A117 (1)C10—C9—H9116.5 (10)
C7—N4—H4B122 (1)C9—C10—C11118.6 (1)
H4A—N4—H4B118 (1)C9—C10—C15122.9 (1)
O2—C5—O3123.7 (2)C11—C10—C15118.5 (1)
O2—C5—C6125.3 (2)C10—C11—C12120.9 (2)
O3—C5—C6111.0 (2)C10—C11—H11118 (1)
O2*—C5*—O3*126 (2)C12—C11—H11120 (1)
O2*—C5*—C6*122 (2)C11—C12—C13119.8 (2)
O3*—C5*—C6*109 (1)C11—C12—H12117 (1)
C5—C6—C6i121.6 (2)C13—C12—H12122 (1)
C5—C6—H6118.5 (9)C12—C13—C14120.3 (2)
C6i—C6—H6119.9 (9)C12—C13—H13119 (1)
C5*—C6*—C6*i129 (2)C14—C13—H13120 (1)
O1—C7—N4122.0 (1)C13—C14—C15120.2 (2)
O1—C7—C8120.9 (1)C13—C14—H14121 (1)
N4—C7—C8117.1 (1)C15—C14—H14117 (1)
C7—C8—C9120.6 (1)C10—C15—C14120.4 (1)
C7—C8—H8115 (1)C10—C15—H15120.4 (10)
C9—C8—H8123 (1)C14—C15—H15119.3 (10)
C8—C9—C10127.9 (1)
Symmetry code: (i) x+1, y+1, z+1.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O3—H3···O1ii0.93 (2)1.65 (2)2.555 (2)163 (2)
N4—H4A···O2iii0.88 (2)2.44 (2)3.288 (2)161 (2)
N4—H4A···O2*iii0.88 (2)2.21 (3)3.08 (2)171 (2)
N4—H4B···O1iv0.89 (2)2.26 (2)3.105 (2)160 (2)
Symmetry codes: (ii) x+1/2, y+1/2, z+1/2; (iii) x+1/2, y1/2, z+1/2; (iv) x, y+1, z.
(I') top
Crystal data top
C4H4O4·(C9H9NO)2Dx = 1.315 Mg m3
Mr = 410.43Mo Kα radiation, λ = 0.71073 Å
Monoclinic, P21/nCell parameters from 25 reflections
a = 11.547 (2) Åθ = 13.5–15.0°
b = 5.354 (2) ŵ = 0.10 mm1
c = 16.820 (2) ÅT = 298 K
β = 94.60 (1)°Prism, colourless
V = 1036.5 (4) Å30.8 × 0.5 × 0.15 mm
Z = 2
Data collection top
Rigaku AFC7R
diffractometer
θmax = 27.5°, θmin = 2.5°
θ–2θ scansh = 015
2482 measured reflectionsk = 07
2367 independent reflectionsl = 2222
1405 reflections with I > 2σ(I)3 standard reflections every 150 reflections
Rint = 0.021 intensity decay: none
Refinement top
Refinement on F2H atoms: see text
R[F2 > 2σ(F2)] = 0.071 w = 1/[σ2(Fo2) + (0.03P)2 + 1.0P]
where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.175(Δ/σ)max = 0.001
S = 1.17Δρmax = 0.32 e Å3
2367 reflectionsΔρmin = 0.21 e Å3
181 parameters
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*/UeqOcc. (<1)
O10.3734 (2)0.1302 (5)0.1976 (2)0.0841 (8)
O20.3879 (3)0.8046 (6)0.4043 (2)0.085 (1)0.852 (6)
O2*0.38670.89000.39620.0853*0.148 (6)
O30.2913 (3)0.4487 (6)0.3939 (2)0.085 (1)0.852 (6)
O3*0.31270.50360.41760.0848*0.148 (6)
N40.3504 (3)0.5444 (7)0.1840 (2)0.089 (1)
C50.3788 (3)0.5855 (8)0.4216 (2)0.062 (1)0.852 (6)
C5*0.38490.69390.43250.0616*0.148 (6)
C60.4609 (3)0.4434 (8)0.4754 (3)0.063 (1)0.852 (6)
C6*0.48420.61190.48870.0627*0.148 (6)
C70.4084 (3)0.3450 (7)0.2110 (2)0.0632 (8)
C80.5215 (3)0.3911 (7)0.2562 (2)0.0623 (8)
C90.5712 (3)0.2167 (7)0.3029 (2)0.0634 (9)
C100.6805 (3)0.2251 (6)0.3518 (2)0.0555 (8)
C110.7064 (4)0.0414 (8)0.4075 (2)0.075 (1)
C120.8081 (4)0.0425 (9)0.4553 (3)0.091 (1)
C130.8870 (4)0.2289 (9)0.4474 (3)0.090 (1)
C140.8649 (4)0.4099 (9)0.3923 (3)0.086 (1)
C150.7631 (3)0.4099 (8)0.3444 (3)0.073 (1)
H30.233 (3)0.528 (8)0.356 (2)0.1072 (2)*0.852 (6)
H4A0.286 (3)0.516 (8)0.164 (2)0.0840 (2)*
H4B0.376 (3)0.695 (8)0.197 (2)0.0892 (2)*
H60.462 (3)0.266 (7)0.476 (2)0.0572 (1)*0.852 (6)
H80.544 (3)0.570 (7)0.256 (2)0.0768 (1)*
H90.523 (3)0.086 (7)0.304 (2)0.0831 (1)*
H110.647 (3)0.068 (8)0.405 (2)0.1090 (2)*
H120.825 (4)0.078 (9)0.495 (3)0.1230 (2)*
H130.958 (3)0.232 (7)0.478 (2)0.0861 (1)*
H140.915 (4)0.523 (8)0.384 (2)0.1046 (2)*
H150.745 (3)0.517 (7)0.317 (2)0.0690 (1)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.067 (2)0.059 (2)0.120 (2)0.002 (1)0.030 (1)0.001 (1)
O20.083 (2)0.064 (2)0.105 (2)0.020 (2)0.020 (2)0.018 (2)
O30.072 (2)0.058 (2)0.116 (3)0.009 (1)0.039 (2)0.003 (2)
N40.075 (2)0.068 (2)0.118 (3)0.014 (2)0.029 (2)0.002 (2)
C50.052 (2)0.057 (2)0.074 (3)0.002 (2)0.003 (2)0.001 (2)
C60.053 (2)0.058 (3)0.076 (3)0.007 (2)0.003 (2)0.002 (2)
C70.056 (2)0.060 (2)0.072 (2)0.009 (2)0.003 (2)0.000 (2)
C80.059 (2)0.051 (2)0.074 (2)0.001 (2)0.010 (2)0.001 (2)
C90.057 (2)0.056 (2)0.076 (2)0.004 (2)0.004 (2)0.005 (2)
C100.051 (2)0.055 (2)0.060 (2)0.003 (1)0.000 (1)0.003 (2)
C110.070 (2)0.071 (2)0.084 (3)0.003 (2)0.002 (2)0.016 (2)
C120.082 (3)0.089 (3)0.099 (3)0.012 (2)0.017 (2)0.022 (3)
C130.069 (2)0.102 (3)0.095 (3)0.013 (2)0.027 (2)0.003 (3)
C140.065 (2)0.089 (3)0.102 (3)0.016 (2)0.013 (2)0.001 (3)
C150.072 (2)0.065 (2)0.079 (3)0.004 (2)0.009 (2)0.013 (2)
Geometric parameters (Å, º) top
O1—C71.234 (4)C8—C91.321 (5)
O2—C51.215 (5)C8—H80.99 (4)
O2*—C5*1.216C9—C101.450 (4)
O3—C51.303 (5)C9—H90.89 (4)
O3—H30.99 (4)C10—C111.375 (5)
O3*—C5*1.328C10—C151.387 (5)
N4—C71.321 (5)C11—C121.369 (6)
N4—H4A0.81 (4)C11—H110.90 (4)
N4—H4B0.88 (4)C12—C131.365 (7)
C5—C61.469 (5)C12—H120.93 (5)
C5*—C6*1.492C13—C141.351 (7)
C6—C6i1.322 (8)C13—H130.93 (3)
C6—H60.95 (4)C14—C151.371 (6)
C6*—C6*i1.300C14—H140.86 (4)
C7—C81.478 (4)C15—H150.75 (3)
C5—O3—H3117 (2)C8—C9—H9109 (2)
C7—N4—H4A114 (2)C10—C9—H9121 (2)
C7—N4—H4B119 (2)C9—C10—C11119.8 (3)
H4A—N4—H4B124 (3)C9—C10—C15123.0 (3)
O2—C5—O3122.5 (4)C11—C10—C15117.2 (3)
O2—C5—C6125.7 (3)C10—C11—C12121.8 (4)
O3—C5—C6111.9 (3)C10—C11—H11108 (2)
O2*—C5*—O3*127.1C12—C11—H11129 (2)
O2*—C5*—C6*121.9C11—C12—C13119.6 (4)
O3*—C5*—C6*109.4C11—C12—H12122 (2)
C5—C6—C6i121.5 (5)C13—C12—H12118 (2)
C5—C6—H6122 (1)C12—C13—C14120.0 (4)
C6i—C6—H6116 (1)C12—C13—H13121 (2)
C5*—C6*—C6*i129.8C14—C13—H13118 (2)
O1—C7—N4122.8 (3)C13—C14—C15120.6 (4)
O1—C7—C8120.9 (3)C13—C14—H14122 (2)
N4—C7—C8116.4 (3)C15—C14—H14117 (2)
C7—C8—C9120.8 (3)C10—C15—C14120.7 (4)
C7—C8—H8112 (1)C10—C15—H15115 (2)
C9—C8—H8125 (1)C14—C15—H15122 (2)
C8—C9—C10129.2 (3)
Symmetry code: (i) x+1, y+1, z+1.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O3—H3···O1ii0.99 (4)1.56 (3)2.542 (4)171 (4)
N4—H4A···O2iii0.81 (4)2.50 (4)3.282 (5)163 (4)
N4—H4A···O2*iii0.81 (4)2.263.067173
N4—H4B···O1iv0.88 (4)2.33 (4)3.154 (5)155 (3)
Symmetry codes: (ii) x+1/2, y+1/2, z+1/2; (iii) x+1/2, y1/2, z+1/2; (iv) x, y+1, z.
 

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