Fumaric acid-trans-cinnamamide (1/2)

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.

Computing details

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)

Crystal data

C4H4O4·2C9H9NO	Dx = 1.328 Mg m^−3
Mr = 410.43	Mo Kα radiation, λ = 0.71073 Å
Monoclinic, P21/n	Cell parameters from 25 reflections
a = 11.505 (2) Å	θ = 13.3–14.9°
b = 5.298 (1) Å	µ = 0.10 mm^−1
c = 16.886 (2) Å	T = 298 K
β = 94.057 (9)°	Prism, colourless
V = 1026.6 (3) Å^3	0.7 × 0.6 × 0.25 mm
Z = 2

Data collection

Rigaku AFC-7R diffractometer	θmax = 27.5°, θmin = 2.5°
θ–2θ scans	h = 0→15
2462 measured reflections	k = −7→0
2351 independent reflections	l = −22→22
1873 reflections with I > 2σ(I)	3 standard reflections every 150 reflections
Rint = 0.007	intensity decay: none

Refinement

Refinement on F^2	w = 1/[σ^2(Fo^2) + (0.0438P)^2 + 0.2732P] where P = (Fo^2 + 2Fc^2)/3
R[F^2 > 2σ(F^2)] = 0.038	(Δ/σ)max = 0.001
wR(F^2) = 0.107	Δρmax = 0.17 e Å^−3
S = 1.06	Δρmin = −0.15 e Å^−3
2351 reflections	Extinction correction: SHELXL97 (Sheldrick, 1997), Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
194 parameters	Extinction coefficient: 0.016 (2)
H atoms: see text

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq	Occ. (<1)
O1	0.37287 (9)	0.1242 (2)	0.19944 (7)	0.0617 (3)
O2	0.3880 (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)
O3	0.2920 (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)
N4	0.3520 (1)	0.5418 (3)	0.1838 (1)	0.0636 (4)
C5	0.3787 (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)
C6	0.4617 (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)
C7	0.4100 (1)	0.3411 (3)	0.21127 (9)	0.0454 (3)
C8	0.5227 (1)	0.3861 (3)	0.25671 (9)	0.0463 (3)
C9	0.5715 (1)	0.2074 (3)	0.30237 (8)	0.0427 (3)
C10	0.6817 (1)	0.2190 (3)	0.35144 (8)	0.0400 (3)
C11	0.7054 (1)	0.0326 (3)	0.4079 (1)	0.0552 (4)
C12	0.8072 (2)	0.0384 (4)	0.4572 (1)	0.0657 (5)
C13	0.8867 (2)	0.2263 (4)	0.4489 (1)	0.0665 (5)
C14	0.8662 (1)	0.4099 (4)	0.3921 (1)	0.0651 (5)
C15	0.7637 (1)	0.4076 (3)	0.34362 (9)	0.0524 (4)
H3	0.239 (2)	0.539 (5)	0.362 (1)	0.09349 (9)*	0.921 (3)
H4A	0.282 (2)	0.518 (4)	0.160 (1)	0.08221 (8)*
H4B	0.375 (2)	0.698 (5)	0.195 (1)	0.09092 (9)*
H6	0.458 (1)	0.262 (3)	0.4740 (10)	0.04677 (6)*	0.921 (3)
H8	0.555 (1)	0.549 (4)	0.252 (1)	0.06350 (6)*
H9	0.529 (1)	0.055 (3)	0.3040 (10)	0.05878 (6)*
H11	0.649 (2)	−0.100 (4)	0.412 (1)	0.07252 (7)*
H12	0.818 (2)	−0.094 (4)	0.496 (1)	0.08459 (8)*
H13	0.957 (2)	0.232 (4)	0.485 (1)	0.09171 (8)*
H14	0.921 (2)	0.542 (4)	0.385 (1)	0.08002 (7)*
H15	0.750 (1)	0.539 (3)	0.304 (1)	0.06406 (6)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0488 (6)	0.0455 (6)	0.0863 (8)	−0.0004 (5)	−0.0277 (5)	−0.0001 (5)
O2	0.0542 (7)	0.0440 (9)	0.0715 (9)	−0.0091 (7)	−0.0198 (6)	0.0123 (8)
O3	0.0532 (7)	0.0426 (7)	0.083 (1)	−0.0047 (5)	−0.0342 (7)	0.0049 (6)
N4	0.0531 (8)	0.0480 (8)	0.086 (1)	0.0080 (6)	−0.0236 (7)	0.0032 (7)
C5	0.0357 (7)	0.0394 (8)	0.0451 (8)	−0.0001 (7)	−0.0064 (6)	−0.0008 (7)
C6	0.0364 (7)	0.0361 (8)	0.0469 (8)	−0.0018 (6)	−0.0043 (6)	0.0016 (6)
C7	0.0395 (7)	0.0426 (7)	0.0526 (8)	0.0032 (6)	−0.0069 (6)	0.0002 (6)
C8	0.0398 (7)	0.0409 (7)	0.0565 (8)	−0.0015 (6)	−0.0081 (6)	0.0003 (6)
C9	0.0362 (6)	0.0408 (7)	0.0505 (7)	−0.0014 (5)	−0.0022 (5)	−0.0006 (6)
C10	0.0353 (6)	0.0421 (7)	0.0419 (6)	0.0035 (5)	−0.0015 (5)	−0.0014 (5)
C11	0.0488 (8)	0.0539 (9)	0.0616 (9)	0.0003 (7)	−0.0050 (7)	0.0122 (7)
C12	0.0613 (10)	0.072 (1)	0.0617 (10)	0.0106 (9)	−0.0140 (8)	0.0167 (9)
C13	0.0498 (9)	0.078 (1)	0.069 (1)	0.0080 (8)	−0.0214 (8)	−0.0048 (9)
C14	0.0454 (8)	0.070 (1)	0.077 (1)	−0.0126 (8)	−0.0133 (8)	0.0019 (9)
C15	0.0451 (8)	0.0535 (9)	0.0572 (9)	−0.0056 (6)	−0.0067 (6)	0.0093 (7)

Geometric parameters (Å, º)

O1—C7	1.237 (2)	C8—C9	1.321 (2)
O2—C5	1.203 (3)	C8—H8	0.94 (2)
O2*—C5*	1.21 (3)	C9—C10	1.465 (2)
O3—C5	1.312 (2)	C9—H9	0.94 (2)
O3—H3	0.923 (2)	C10—C11	1.387 (2)
O3*—C5*	1.32 (3)	C10—C15	1.387 (2)
N4—C7	1.322 (2)	C11—C12	1.388 (2)
N4—H4A	0.88 (2)	C11—H11	0.96 (2)
N4—H4B	0.89 (2)	C12—C13	1.367 (3)
C5—C6	1.489 (2)	C12—H12	0.96 (2)
C5*—C6*	1.50 (2)	C13—C14	1.374 (3)
C6—C6^i	1.314 (3)	C13—H13	0.97 (2)
C6—H6	0.96 (2)	C14—C15	1.388 (2)
C6*—C6*^i	1.29 (4)	C14—H14	0.96 (2)
C7—C8	1.479 (2)	C15—H15	0.97 (2)
C5—O3—H3	110 (1)	C8—C9—H9	115.5 (10)
C7—N4—H4A	117 (1)	C10—C9—H9	116.5 (10)
C7—N4—H4B	122 (1)	C9—C10—C11	118.6 (1)
H4A—N4—H4B	118 (1)	C9—C10—C15	122.9 (1)
O2—C5—O3	123.7 (2)	C11—C10—C15	118.5 (1)
O2—C5—C6	125.3 (2)	C10—C11—C12	120.9 (2)
O3—C5—C6	111.0 (2)	C10—C11—H11	118 (1)
O2*—C5*—O3*	126 (2)	C12—C11—H11	120 (1)
O2*—C5*—C6*	122 (2)	C11—C12—C13	119.8 (2)
O3*—C5*—C6*	109 (1)	C11—C12—H12	117 (1)
C5—C6—C6^i	121.6 (2)	C13—C12—H12	122 (1)
C5—C6—H6	118.5 (9)	C12—C13—C14	120.3 (2)
C6^i—C6—H6	119.9 (9)	C12—C13—H13	119 (1)
C5*—C6*—C6*^i	129 (2)	C14—C13—H13	120 (1)
O1—C7—N4	122.0 (1)	C13—C14—C15	120.2 (2)
O1—C7—C8	120.9 (1)	C13—C14—H14	121 (1)
N4—C7—C8	117.1 (1)	C15—C14—H14	117 (1)
C7—C8—C9	120.6 (1)	C10—C15—C14	120.4 (1)
C7—C8—H8	115 (1)	C10—C15—H15	120.4 (10)
C9—C8—H8	123 (1)	C14—C15—H15	119.3 (10)
C8—C9—C10	127.9 (1)

Symmetry code: (i) −x+1, −y+1, −z+1.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3···O1^ii	0.93 (2)	1.65 (2)	2.555 (2)	163 (2)
N4—H4A···O2^iii	0.88 (2)	2.44 (2)	3.288 (2)	161 (2)
N4—H4A···O2*^iii	0.88 (2)	2.21 (3)	3.08 (2)	171 (2)
N4—H4B···O1^iv	0.89 (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, y−1/2, −z+1/2; (iv) x, y+1, z.

(I')

Crystal data

C4H4O4·(C9H9NO)2	Dx = 1.315 Mg m^−3
Mr = 410.43	Mo Kα radiation, λ = 0.71073 Å
Monoclinic, P21/n	Cell parameters from 25 reflections
a = 11.547 (2) Å	θ = 13.5–15.0°
b = 5.354 (2) Å	µ = 0.10 mm^−1
c = 16.820 (2) Å	T = 298 K
β = 94.60 (1)°	Prism, colourless
V = 1036.5 (4) Å^3	0.8 × 0.5 × 0.15 mm
Z = 2

Data collection

Rigaku AFC7R diffractometer	θmax = 27.5°, θmin = 2.5°
θ–2θ scans	h = 0→15
2482 measured reflections	k = 0→7
2367 independent reflections	l = −22→22
1405 reflections with I > 2σ(I)	3 standard reflections every 150 reflections
Rint = 0.021	intensity decay: none

Refinement

Refinement on F^2	H atoms: see text
R[F^2 > 2σ(F^2)] = 0.071	w = 1/[σ^2(Fo^2) + (0.03P)^2 + 1.0P] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.175	(Δ/σ)max = 0.001
S = 1.17	Δρmax = 0.32 e Å^−3
2367 reflections	Δρmin = −0.21 e Å^−3
181 parameters

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq	Occ. (<1)
O1	0.3734 (2)	0.1302 (5)	0.1976 (2)	0.0841 (8)
O2	0.3879 (3)	0.8046 (6)	0.4043 (2)	0.085 (1)	0.852 (6)
O2*	0.3867	0.8900	0.3962	0.0853*	0.148 (6)
O3	0.2913 (3)	0.4487 (6)	0.3939 (2)	0.085 (1)	0.852 (6)
O3*	0.3127	0.5036	0.4176	0.0848*	0.148 (6)
N4	0.3504 (3)	0.5444 (7)	0.1840 (2)	0.089 (1)
C5	0.3788 (3)	0.5855 (8)	0.4216 (2)	0.062 (1)	0.852 (6)
C5*	0.3849	0.6939	0.4325	0.0616*	0.148 (6)
C6	0.4609 (3)	0.4434 (8)	0.4754 (3)	0.063 (1)	0.852 (6)
C6*	0.4842	0.6119	0.4887	0.0627*	0.148 (6)
C7	0.4084 (3)	0.3450 (7)	0.2110 (2)	0.0632 (8)
C8	0.5215 (3)	0.3911 (7)	0.2562 (2)	0.0623 (8)
C9	0.5712 (3)	0.2167 (7)	0.3029 (2)	0.0634 (9)
C10	0.6805 (3)	0.2251 (6)	0.3518 (2)	0.0555 (8)
C11	0.7064 (4)	0.0414 (8)	0.4075 (2)	0.075 (1)
C12	0.8081 (4)	0.0425 (9)	0.4553 (3)	0.091 (1)
C13	0.8870 (4)	0.2289 (9)	0.4474 (3)	0.090 (1)
C14	0.8649 (4)	0.4099 (9)	0.3923 (3)	0.086 (1)
C15	0.7631 (3)	0.4099 (8)	0.3444 (3)	0.073 (1)
H3	0.233 (3)	0.528 (8)	0.356 (2)	0.1072 (2)*	0.852 (6)
H4A	0.286 (3)	0.516 (8)	0.164 (2)	0.0840 (2)*
H4B	0.376 (3)	0.695 (8)	0.197 (2)	0.0892 (2)*
H6	0.462 (3)	0.266 (7)	0.476 (2)	0.0572 (1)*	0.852 (6)
H8	0.544 (3)	0.570 (7)	0.256 (2)	0.0768 (1)*
H9	0.523 (3)	0.086 (7)	0.304 (2)	0.0831 (1)*
H11	0.647 (3)	−0.068 (8)	0.405 (2)	0.1090 (2)*
H12	0.825 (4)	−0.078 (9)	0.495 (3)	0.1230 (2)*
H13	0.958 (3)	0.232 (7)	0.478 (2)	0.0861 (1)*
H14	0.915 (4)	0.523 (8)	0.384 (2)	0.1046 (2)*
H15	0.745 (3)	0.517 (7)	0.317 (2)	0.0690 (1)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.067 (2)	0.059 (2)	0.120 (2)	−0.002 (1)	−0.030 (1)	−0.001 (1)
O2	0.083 (2)	0.064 (2)	0.105 (2)	−0.020 (2)	−0.020 (2)	0.018 (2)
O3	0.072 (2)	0.058 (2)	0.116 (3)	−0.009 (1)	−0.039 (2)	0.003 (2)
N4	0.075 (2)	0.068 (2)	0.118 (3)	0.014 (2)	−0.029 (2)	−0.002 (2)
C5	0.052 (2)	0.057 (2)	0.074 (3)	−0.002 (2)	−0.003 (2)	−0.001 (2)
C6	0.053 (2)	0.058 (3)	0.076 (3)	−0.007 (2)	−0.003 (2)	−0.002 (2)
C7	0.056 (2)	0.060 (2)	0.072 (2)	0.009 (2)	−0.003 (2)	0.000 (2)
C8	0.059 (2)	0.051 (2)	0.074 (2)	0.001 (2)	−0.010 (2)	−0.001 (2)
C9	0.057 (2)	0.056 (2)	0.076 (2)	−0.004 (2)	−0.004 (2)	0.005 (2)
C10	0.051 (2)	0.055 (2)	0.060 (2)	0.003 (1)	0.000 (1)	−0.003 (2)
C11	0.070 (2)	0.071 (2)	0.084 (3)	0.003 (2)	−0.002 (2)	0.016 (2)
C12	0.082 (3)	0.089 (3)	0.099 (3)	0.012 (2)	−0.017 (2)	0.022 (3)
C13	0.069 (2)	0.102 (3)	0.095 (3)	0.013 (2)	−0.027 (2)	−0.003 (3)
C14	0.065 (2)	0.089 (3)	0.102 (3)	−0.016 (2)	−0.013 (2)	0.001 (3)
C15	0.072 (2)	0.065 (2)	0.079 (3)	−0.004 (2)	−0.009 (2)	0.013 (2)

Geometric parameters (Å, º)

O1—C7	1.234 (4)	C8—C9	1.321 (5)
O2—C5	1.215 (5)	C8—H8	0.99 (4)
O2*—C5*	1.216	C9—C10	1.450 (4)
O3—C5	1.303 (5)	C9—H9	0.89 (4)
O3—H3	0.99 (4)	C10—C11	1.375 (5)
O3*—C5*	1.328	C10—C15	1.387 (5)
N4—C7	1.321 (5)	C11—C12	1.369 (6)
N4—H4A	0.81 (4)	C11—H11	0.90 (4)
N4—H4B	0.88 (4)	C12—C13	1.365 (7)
C5—C6	1.469 (5)	C12—H12	0.93 (5)
C5*—C6*	1.492	C13—C14	1.351 (7)
C6—C6^i	1.322 (8)	C13—H13	0.93 (3)
C6—H6	0.95 (4)	C14—C15	1.371 (6)
C6*—C6*^i	1.300	C14—H14	0.86 (4)
C7—C8	1.478 (4)	C15—H15	0.75 (3)
C5—O3—H3	117 (2)	C8—C9—H9	109 (2)
C7—N4—H4A	114 (2)	C10—C9—H9	121 (2)
C7—N4—H4B	119 (2)	C9—C10—C11	119.8 (3)
H4A—N4—H4B	124 (3)	C9—C10—C15	123.0 (3)
O2—C5—O3	122.5 (4)	C11—C10—C15	117.2 (3)
O2—C5—C6	125.7 (3)	C10—C11—C12	121.8 (4)
O3—C5—C6	111.9 (3)	C10—C11—H11	108 (2)
O2*—C5*—O3*	127.1	C12—C11—H11	129 (2)
O2*—C5*—C6*	121.9	C11—C12—C13	119.6 (4)
O3*—C5*—C6*	109.4	C11—C12—H12	122 (2)
C5—C6—C6^i	121.5 (5)	C13—C12—H12	118 (2)
C5—C6—H6	122 (1)	C12—C13—C14	120.0 (4)
C6^i—C6—H6	116 (1)	C12—C13—H13	121 (2)
C5*—C6*—C6*^i	129.8	C14—C13—H13	118 (2)
O1—C7—N4	122.8 (3)	C13—C14—C15	120.6 (4)
O1—C7—C8	120.9 (3)	C13—C14—H14	122 (2)
N4—C7—C8	116.4 (3)	C15—C14—H14	117 (2)
C7—C8—C9	120.8 (3)	C10—C15—C14	120.7 (4)
C7—C8—H8	112 (1)	C10—C15—H15	115 (2)
C9—C8—H8	125 (1)	C14—C15—H15	122 (2)
C8—C9—C10	129.2 (3)

Symmetry code: (i) −x+1, −y+1, −z+1.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3···O1^ii	0.99 (4)	1.56 (3)	2.542 (4)	171 (4)
N4—H4A···O2^iii	0.81 (4)	2.50 (4)	3.282 (5)	163 (4)
N4—H4A···O2*^iii	0.81 (4)	2.26	3.067	173
N4—H4B···O1^iv	0.88 (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, y−1/2, −z+1/2; (iv) x, y+1, z.