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In crystals of the title compound, the hydrogen fumarate anions form one-dimensional chains through an O-H
O hydrogen bonding along the
c and (
a+
b)/2 directions. There are three sites of the hydrogen fumarate, two of which have an inversion centre.
Supporting information
CCDC reference: 144698
The crystals of (I) were grown from a diethyl ether/2-propanol solution.
All H atoms were located from difference syntheses and were refined
isotropically. The C—H bond distances are in the range 0.89 (2)–1.05 (4) Å,
the N—H distances are 0.87 (2) and 0.90 (2) Å, and the O—H distance is
1.08 (3) Å, except for those involving the H5 atom.
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); software used to prepare material for publication: TEXSAN.
Crystal data top
C6H16N+·C4H3O4− | Z = 4 |
Mr = 217.26 | Dx = 1.166 Mg m−3 |
Triclinic, P1 | Mo Kα radiation, λ = 0.71073 Å |
a = 13.409 (3) Å | Cell parameters from 25 reflections |
b = 13.656 (3) Å | θ = 14.4–15.0° |
c = 7.432 (2) Å | µ = 0.09 mm−1 |
α = 95.03 (3)° | T = 295 K |
β = 90.11 (2)° | Prism, colourless |
γ = 113.99 (1)° | 0.6 × 0.6 × 0.4 mm |
V = 1237.5 (5) Å3 | |
Data collection top
Rigaku AFC5 diffractometer | θmax = 26.0°, θmin = 2.0° |
θ–2θ scans | h = 0→17 |
5071 measured reflections | k = −17→17 |
4850 independent reflections | l = −9→9 |
3040 reflections with I > 2σ(I) | 3 standard reflections every 100 reflections |
Rint = 0.016 | intensity decay: 4.4% |
Refinement top
Refinement on F2 | w = 1/[σ2(Fo2) + (0.051P)2 + 0.1858P] where P = (Fo2 + 2Fc2)/3 |
R[F2 > 2σ(F2)] = 0.045 | (Δ/σ)max = 0.001 |
wR(F2) = 0.117 | Δρmax = 0.21 e Å−3 |
S = 1.02 | Δρmin = −0.12 e Å−3 |
4850 reflections | Extinction correction: SHELXL97 (Sheldrick, 1997), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
424 parameters | Extinction coefficient: 0.026 (2) |
All H-atom parameters refined | |
Crystal data top
C6H16N+·C4H3O4− | γ = 113.99 (1)° |
Mr = 217.26 | V = 1237.5 (5) Å3 |
Triclinic, P1 | Z = 4 |
a = 13.409 (3) Å | Mo Kα radiation |
b = 13.656 (3) Å | µ = 0.09 mm−1 |
c = 7.432 (2) Å | T = 295 K |
α = 95.03 (3)° | 0.6 × 0.6 × 0.4 mm |
β = 90.11 (2)° | |
Data collection top
Rigaku AFC5 diffractometer | Rint = 0.016 |
5071 measured reflections | 3 standard reflections every 100 reflections |
4850 independent reflections | intensity decay: 4.4% |
3040 reflections with I > 2σ(I) | |
Refinement top
R[F2 > 2σ(F2)] = 0.045 | 424 parameters |
wR(F2) = 0.117 | All H-atom parameters refined |
S = 1.02 | Δρmax = 0.21 e Å−3 |
4850 reflections | Δρmin = −0.12 e Å−3 |
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 | x | y | z | Uiso*/Ueq | |
O1 | 0.7149 (1) | 0.2734 (1) | 0.8165 (2) | 0.0790 (5) | |
O2 | 0.5465 (1) | 0.1503 (1) | 0.7510 (2) | 0.0644 (4) | |
O3 | 0.6783 (1) | 0.2505 (1) | 0.1407 (2) | 0.0724 (5) | |
O4 | 0.8513 (1) | 0.3609 (1) | 0.2025 (2) | 0.0660 (4) | |
O5 | 0.8233 (1) | −0.1624 (1) | 0.4545 (2) | 0.0537 (4) | |
O6 | 0.8579 (1) | −0.1450 (1) | 0.7516 (2) | 0.0636 (4) | |
O7 | 0.6549 (1) | −0.3208 (1) | 0.4898 (2) | 0.0684 (5) | |
O8 | 0.7092 (1) | −0.4316 (1) | 0.3233 (2) | 0.0714 (5) | |
N9 | 0.6003 (1) | −0.1378 (1) | 0.9926 (2) | 0.0488 (4) | |
N10 | 0.8992 (1) | −0.3563 (1) | 0.1308 (2) | 0.0498 (4) | |
C11 | 0.6366 (2) | 0.2156 (2) | 0.7091 (2) | 0.0509 (5) | |
C12 | 0.6544 (2) | 0.2258 (2) | 0.5117 (3) | 0.0550 (5) | |
C13 | 0.7388 (2) | 0.2973 (2) | 0.4453 (2) | 0.0519 (5) | |
C14 | 0.7610 (2) | 0.3063 (2) | 0.2501 (2) | 0.0478 (5) | |
C15 | 0.8812 (1) | −0.1167 (1) | 0.6008 (3) | 0.0430 (4) | |
C16 | 0.9843 (2) | −0.0206 (1) | 0.5768 (3) | 0.0435 (4) | |
C17 | 0.6443 (1) | −0.4130 (2) | 0.4212 (3) | 0.0476 (5) | |
C18 | 0.5417 (2) | −0.5048 (2) | 0.4629 (3) | 0.0479 (5) | |
C19 | 0.5884 (2) | −0.0611 (2) | 0.8697 (3) | 0.0562 (5) | |
C20 | 0.6635 (3) | −0.0396 (3) | 0.7138 (4) | 0.0822 (9) | |
C21 | 0.7063 (2) | −0.0938 (2) | 1.1004 (3) | 0.0659 (6) | |
C22 | 0.7241 (3) | 0.0054 (3) | 1.2208 (4) | 0.0799 (8) | |
C23 | 0.5769 (3) | −0.2453 (2) | 0.8914 (3) | 0.0673 (6) | |
C24 | 0.5422 (4) | −0.3348 (3) | 1.0123 (5) | 0.098 (1) | |
C25 | 0.9282 (2) | −0.2414 (2) | 0.0972 (4) | 0.0572 (6) | |
C26 | 1.0368 (3) | −0.1878 (3) | 0.0141 (5) | 0.0865 (9) | |
C27 | 0.8772 (2) | −0.4305 (2) | −0.0402 (3) | 0.0646 (6) | |
C28 | 0.7815 (3) | −0.4362 (3) | −0.1515 (5) | 0.0878 (9) | |
C29 | 0.9795 (2) | −0.3709 (2) | 0.2549 (4) | 0.0685 (7) | |
C30 | 0.9897 (3) | −0.3115 (4) | 0.4387 (5) | 0.101 (1) | |
H3 | 0.699 (3) | 0.260 (2) | 0.001 (4) | 0.1281 (1)* | |
H5 | 0.744 (3) | −0.242 (2) | 0.473 (4) | 0.1210 (1)* | |
H9 | 0.546 (2) | −0.149 (2) | 1.071 (3) | 0.05829 (8)* | |
H10 | 0.838 (2) | −0.376 (2) | 0.186 (3) | 0.05359 (7)* | |
H12 | 0.599 (2) | 0.175 (2) | 0.435 (3) | 0.07964 (10)* | |
H13 | 0.794 (2) | 0.349 (2) | 0.528 (3) | 0.06794 (8)* | |
H16 | 1.027 (2) | 0.012 (2) | 0.687 (3) | 0.05385 (7)* | |
H18 | 0.540 (2) | −0.570 (2) | 0.432 (3) | 0.04613 (7)* | |
H19A | 0.602 (2) | 0.006 (2) | 0.945 (3) | 0.06567 (8)* | |
H19B | 0.510 (2) | −0.094 (2) | 0.824 (3) | 0.07506 (9)* | |
H20A | 0.651 (2) | −0.107 (2) | 0.644 (4) | 0.0917 (1)* | |
H20B | 0.646 (2) | 0.010 (3) | 0.642 (4) | 0.1146 (1)* | |
H20C | 0.744 (3) | −0.009 (3) | 0.769 (5) | 0.1402 (2)* | |
H21A | 0.763 (2) | −0.081 (2) | 1.011 (4) | 0.0883 (1)* | |
H21B | 0.701 (2) | −0.152 (2) | 1.171 (3) | 0.07443 (9)* | |
H22A | 0.665 (2) | −0.001 (2) | 1.295 (4) | 0.0863 (1)* | |
H22B | 0.789 (3) | 0.023 (2) | 1.302 (4) | 0.1108 (1)* | |
H22C | 0.734 (2) | 0.066 (2) | 1.152 (4) | 0.1043 (1)* | |
H23A | 0.646 (2) | −0.237 (2) | 0.825 (3) | 0.08292 (10)* | |
H23B | 0.516 (2) | −0.257 (2) | 0.799 (4) | 0.0882 (1)* | |
H24A | 0.529 (2) | −0.399 (3) | 0.943 (4) | 0.1083 (1)* | |
H24B | 0.608 (3) | −0.317 (3) | 1.098 (5) | 0.1450 (2)* | |
H24C | 0.485 (3) | −0.338 (3) | 1.079 (5) | 0.1221 (2)* | |
H25A | 0.926 (2) | −0.207 (2) | 0.206 (3) | 0.07549 (9)* | |
H25B | 0.873 (2) | −0.244 (2) | 0.017 (3) | 0.06133 (8)* | |
H26A | 1.037 (3) | −0.228 (3) | −0.104 (5) | 0.1308 (2)* | |
H26B | 1.098 (3) | −0.184 (2) | 0.097 (4) | 0.1148 (1)* | |
H26C | 1.049 (2) | −0.117 (3) | 0.005 (4) | 0.1065 (1)* | |
H27A | 0.947 (2) | −0.406 (2) | −0.096 (3) | 0.06638 (8)* | |
H27B | 0.867 (2) | −0.500 (3) | 0.000 (4) | 0.1053 (1)* | |
H28A | 0.768 (3) | −0.493 (3) | −0.243 (5) | 0.1163 (1)* | |
H28B | 0.720 (3) | −0.452 (3) | −0.083 (5) | 0.1206 (2)* | |
H28C | 0.801 (3) | −0.363 (3) | −0.195 (5) | 0.1533 (2)* | |
H29A | 1.047 (2) | −0.348 (2) | 0.193 (3) | 0.07096 (8)* | |
H29B | 0.951 (2) | −0.450 (3) | 0.267 (4) | 0.1068 (1)* | |
H30A | 0.915 (3) | −0.335 (3) | 0.483 (5) | 0.1386 (2)* | |
H30B | 1.033 (4) | −0.233 (4) | 0.422 (6) | 0.1818 (3)* | |
H30C | 1.029 (3) | −0.342 (3) | 0.523 (5) | 0.1442 (2)* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O1 | 0.071 (1) | 0.110 (1) | 0.0270 (7) | 0.0062 (9) | 0.0055 (7) | 0.0147 (8) |
O2 | 0.0617 (9) | 0.078 (1) | 0.0426 (8) | 0.0162 (8) | 0.0213 (7) | 0.0122 (7) |
O3 | 0.0564 (9) | 0.108 (1) | 0.0281 (7) | 0.0059 (9) | 0.0053 (7) | 0.0162 (8) |
O4 | 0.0544 (9) | 0.086 (1) | 0.0457 (8) | 0.0133 (8) | 0.0144 (7) | 0.0195 (7) |
O5 | 0.0418 (7) | 0.0451 (8) | 0.0524 (8) | −0.0044 (6) | 0.0092 (6) | 0.0034 (6) |
O6 | 0.0549 (9) | 0.0671 (9) | 0.0556 (9) | 0.0083 (7) | 0.0135 (7) | 0.0221 (7) |
O7 | 0.0457 (8) | 0.0460 (9) | 0.085 (1) | −0.0078 (7) | 0.0254 (7) | −0.0082 (8) |
O8 | 0.0483 (8) | 0.0648 (9) | 0.085 (1) | 0.0071 (7) | 0.0347 (8) | 0.0044 (8) |
N9 | 0.0532 (10) | 0.057 (1) | 0.0396 (9) | 0.0253 (8) | 0.0145 (8) | 0.0080 (7) |
N10 | 0.0397 (9) | 0.057 (1) | 0.0530 (10) | 0.0174 (8) | 0.0161 (8) | 0.0159 (8) |
C11 | 0.059 (1) | 0.063 (1) | 0.0292 (9) | 0.022 (1) | 0.0105 (9) | 0.0098 (9) |
C12 | 0.052 (1) | 0.074 (1) | 0.0286 (10) | 0.014 (1) | 0.0036 (9) | 0.0077 (10) |
C13 | 0.049 (1) | 0.069 (1) | 0.0297 (9) | 0.016 (1) | 0.0037 (9) | 0.0062 (9) |
C14 | 0.051 (1) | 0.060 (1) | 0.0322 (9) | 0.0205 (10) | 0.0087 (9) | 0.0111 (9) |
C15 | 0.0367 (10) | 0.0372 (10) | 0.051 (1) | 0.0097 (8) | 0.0133 (9) | 0.0086 (9) |
C16 | 0.0369 (10) | 0.0368 (10) | 0.048 (1) | 0.0061 (8) | 0.0066 (8) | 0.0019 (8) |
C17 | 0.0330 (10) | 0.050 (1) | 0.044 (1) | 0.0016 (8) | 0.0087 (8) | 0.0040 (9) |
C18 | 0.038 (1) | 0.039 (1) | 0.050 (1) | 0.0004 (9) | 0.0098 (8) | −0.0029 (9) |
C19 | 0.063 (1) | 0.069 (1) | 0.046 (1) | 0.034 (1) | 0.010 (1) | 0.011 (1) |
C20 | 0.112 (3) | 0.097 (2) | 0.064 (2) | 0.065 (2) | 0.041 (2) | 0.036 (2) |
C21 | 0.060 (1) | 0.091 (2) | 0.052 (1) | 0.036 (1) | 0.003 (1) | 0.010 (1) |
C22 | 0.065 (2) | 0.097 (2) | 0.061 (2) | 0.019 (2) | 0.001 (1) | −0.007 (2) |
C23 | 0.087 (2) | 0.063 (1) | 0.058 (1) | 0.037 (1) | 0.013 (1) | 0.006 (1) |
C24 | 0.138 (3) | 0.067 (2) | 0.093 (2) | 0.045 (2) | 0.025 (3) | 0.017 (2) |
C25 | 0.062 (1) | 0.053 (1) | 0.056 (1) | 0.023 (1) | 0.016 (1) | 0.010 (1) |
C26 | 0.069 (2) | 0.066 (2) | 0.107 (3) | 0.007 (1) | 0.028 (2) | 0.028 (2) |
C27 | 0.069 (2) | 0.059 (1) | 0.065 (1) | 0.025 (1) | 0.019 (1) | 0.006 (1) |
C28 | 0.090 (2) | 0.092 (2) | 0.072 (2) | 0.029 (2) | −0.007 (2) | −0.008 (2) |
C29 | 0.053 (1) | 0.082 (2) | 0.078 (2) | 0.033 (1) | 0.009 (1) | 0.020 (1) |
C30 | 0.092 (2) | 0.155 (4) | 0.074 (2) | 0.070 (3) | −0.009 (2) | 0.003 (2) |
Geometric parameters (Å, º) top
O1—C11 | 1.255 (2) | C20—H20A | 0.97 (3) |
O2—C11 | 1.235 (2) | C20—H20B | 0.99 (4) |
O3—C14 | 1.293 (2) | C20—H20C | 1.05 (4) |
O3—H3 | 1.08 (3) | C21—C22 | 1.488 (4) |
O4—C14 | 1.208 (2) | C21—H21A | 0.98 (3) |
O5—C15 | 1.288 (2) | C21—H21B | 0.97 (3) |
O5—H5 | 1.19 (3) | C22—H22A | 0.95 (3) |
O6—C15 | 1.217 (2) | C22—H22B | 0.99 (3) |
O7—C17 | 1.268 (3) | C22—H22C | 0.97 (3) |
O7—H5 | 1.26 (3) | C23—C24 | 1.500 (5) |
O8—C17 | 1.226 (3) | C23—H23A | 1.02 (3) |
N9—C19 | 1.503 (4) | C23—H23B | 1.02 (3) |
N9—C21 | 1.497 (3) | C24—H24A | 0.93 (3) |
N9—C23 | 1.500 (3) | C24—H24B | 1.01 (4) |
N9—H9 | 0.90 (2) | C24—H24C | 0.90 (4) |
N10—C25 | 1.500 (3) | C25—C26 | 1.502 (4) |
N10—C27 | 1.503 (3) | C25—H25A | 0.91 (3) |
N10—C29 | 1.501 (4) | C25—H25B | 0.94 (3) |
N10—H10 | 0.87 (2) | C26—H26A | 0.99 (4) |
C11—C12 | 1.497 (3) | C26—H26B | 1.01 (4) |
C12—C13 | 1.290 (3) | C26—H26C | 0.92 (4) |
C12—H12 | 0.93 (2) | C27—C28 | 1.496 (5) |
C13—C14 | 1.487 (3) | C27—H27A | 0.97 (2) |
C13—H13 | 0.96 (2) | C27—H27B | 0.98 (4) |
C15—C16 | 1.493 (2) | C28—H28A | 0.95 (3) |
C16—C16i | 1.312 (4) | C28—H28B | 0.93 (4) |
C16—H16 | 0.97 (2) | C28—H28C | 1.01 (5) |
C17—C18 | 1.493 (2) | C29—C30 | 1.502 (5) |
C18—C18ii | 1.296 (4) | C29—H29A | 0.96 (2) |
C18—H18 | 0.89 (2) | C29—H29B | 1.01 (3) |
C19—C20 | 1.506 (4) | C30—H30A | 0.99 (4) |
C19—H19A | 0.97 (2) | C30—H30B | 1.00 (5) |
C19—H19B | 1.00 (3) | C30—H30C | 1.03 (5) |
| | | |
C14—O3—H3 | 111 (1) | H21A—C21—H21B | 111 (2) |
C15—O5—H5 | 114 (1) | C21—C22—H22A | 113 (1) |
C17—O7—H5 | 118 (1) | C21—C22—H22B | 109 (2) |
C19—N9—C21 | 114.1 (2) | C21—C22—H22C | 111 (1) |
C19—N9—C23 | 111.1 (2) | H22A—C22—H22B | 107 (2) |
C19—N9—H9 | 104 (1) | H22A—C22—H22C | 104 (2) |
C21—N9—C23 | 112.5 (2) | H22B—C22—H22C | 109 (2) |
C21—N9—H9 | 107 (1) | N9—C23—C24 | 112.7 (2) |
C23—N9—H9 | 105 (1) | N9—C23—H23A | 106 (1) |
C25—N10—C27 | 113.1 (2) | N9—C23—H23B | 105 (1) |
C25—N10—C29 | 113.9 (2) | C24—C23—H23A | 112 (1) |
C25—N10—H10 | 105 (1) | C24—C23—H23B | 110 (1) |
C27—N10—C29 | 110.9 (2) | H23A—C23—H23B | 108 (2) |
C27—N10—H10 | 106 (1) | C23—C24—H24A | 108 (2) |
C29—N10—H10 | 106 (1) | C23—C24—H24B | 104 (2) |
O1—C11—O2 | 126.1 (2) | C23—C24—H24C | 112 (2) |
O1—C11—C12 | 117.0 (2) | H24A—C24—H24B | 109 (3) |
O2—C11—C12 | 116.9 (2) | H24A—C24—H24C | 112 (2) |
C11—C12—C13 | 124.9 (2) | H24B—C24—H24C | 108 (3) |
C11—C12—H12 | 114 (1) | N10—C25—C26 | 114.3 (3) |
C13—C12—H12 | 120 (1) | N10—C25—H25A | 105 (1) |
C12—C13—C14 | 126.1 (2) | N10—C25—H25B | 104 (1) |
C12—C13—H13 | 118 (1) | C26—C25—H25A | 111 (1) |
C14—C13—H13 | 115 (1) | C26—C25—H25B | 109 (1) |
O3—C14—O4 | 124.3 (2) | H25A—C25—H25B | 111 (2) |
O3—C14—C13 | 115.0 (2) | C25—C26—H26A | 109 (1) |
O4—C14—C13 | 120.7 (2) | C25—C26—H26B | 110 (1) |
O5—C15—O6 | 125.6 (1) | C25—C26—H26C | 107 (2) |
O5—C15—C16 | 115.1 (2) | H26A—C26—H26B | 110 (3) |
O6—C15—C16 | 119.4 (2) | H26A—C26—H26C | 113 (2) |
C15—C16—C16i | 125.1 (2) | H26B—C26—H26C | 104 (2) |
C15—C16—H16 | 113 (1) | N10—C27—C28 | 113.2 (3) |
C16i—C16—H16 | 120 (1) | N10—C27—H27A | 103 (1) |
O7—C17—O8 | 125.7 (2) | N10—C27—H27B | 104 (1) |
O7—C17—C18 | 115.6 (2) | C28—C27—H27A | 117 (1) |
O8—C17—C18 | 118.7 (2) | C28—C27—H27B | 112 (1) |
C17—C18—C18ii | 124.9 (3) | H27A—C27—H27B | 103 (2) |
C17—C18—H18 | 114 (1) | C27—C28—H28A | 105 (2) |
C18ii—C18—H18 | 120 (1) | C27—C28—H28B | 110 (2) |
N9—C19—C20 | 114.2 (3) | C27—C28—H28C | 107 (2) |
N9—C19—H19A | 106 (1) | H28A—C28—H28B | 108 (2) |
N9—C19—H19B | 106 (1) | H28A—C28—H28C | 115 (3) |
C20—C19—H19A | 110 (1) | H28B—C28—H28C | 108 (3) |
C20—C19—H19B | 110 (1) | N10—C29—C30 | 112.4 (3) |
H19A—C19—H19B | 108 (2) | N10—C29—H29A | 105 (1) |
C19—C20—H20A | 109 (1) | N10—C29—H29B | 106 (1) |
C19—C20—H20B | 106 (1) | C30—C29—H29A | 113 (1) |
C19—C20—H20C | 107 (2) | C30—C29—H29B | 109 (1) |
H20A—C20—H20B | 112 (2) | H29A—C29—H29B | 110 (2) |
H20A—C20—H20C | 106 (2) | C29—C30—H30A | 106 (1) |
H20B—C20—H20C | 115 (2) | C29—C30—H30B | 105 (2) |
N9—C21—C22 | 113.4 (3) | C29—C30—H30C | 106 (2) |
N9—C21—H21A | 105 (1) | H30A—C30—H30B | 119 (4) |
N9—C21—H21B | 103 (1) | H30A—C30—H30C | 104 (3) |
C22—C21—H21A | 111 (1) | H30B—C30—H30C | 113 (3) |
C22—C21—H21B | 110 (1) | | |
Symmetry codes: (i) −x+2, −y, −z+1; (ii) −x+1, −y−1, −z+1. |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O3—H3···O1iii | 1.08 (3) | 1.40 (3) | 2.481 (2) | 174 (3) |
O5—H5···O7 | 1.19 (3) | 1.26 (3) | 2.445 (2) | 175 (4) |
N9—H9···O2iv | 0.90 (2) | 1.81 (2) | 2.708 (2) | 170 (2) |
N10—H10···O8 | 0.87 (2) | 1.92 (2) | 2.781 (2) | 173 (2) |
Symmetry codes: (iii) x, y, z−1; (iv) −x+1, −y, −z+2. |
Experimental details
Crystal data |
Chemical formula | C6H16N+·C4H3O4− |
Mr | 217.26 |
Crystal system, space group | Triclinic, P1 |
Temperature (K) | 295 |
a, b, c (Å) | 13.409 (3), 13.656 (3), 7.432 (2) |
α, β, γ (°) | 95.03 (3), 90.11 (2), 113.99 (1) |
V (Å3) | 1237.5 (5) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.09 |
Crystal size (mm) | 0.6 × 0.6 × 0.4 |
|
Data collection |
Diffractometer | Rigaku AFC5 diffractometer |
Absorption correction | – |
No. of measured, independent and observed [I > 2σ(I)] reflections | 5071, 4850, 3040 |
Rint | 0.016 |
(sin θ/λ)max (Å−1) | 0.617 |
|
Refinement |
R[F2 > 2σ(F2)], wR(F2), S | 0.045, 0.117, 1.02 |
No. of reflections | 4850 |
No. of parameters | 424 |
No. of restraints | ? |
H-atom treatment | All H-atom parameters refined |
Δρmax, Δρmin (e Å−3) | 0.21, −0.12 |
Selected geometric parameters (Å, º) topO1—C11 | 1.255 (2) | O5—C15 | 1.288 (2) |
O2—C11 | 1.235 (2) | O6—C15 | 1.217 (2) |
O3—C14 | 1.293 (2) | O7—C17 | 1.268 (3) |
O4—C14 | 1.208 (2) | O8—C17 | 1.226 (3) |
| | | |
O1—C11—O2 | 126.1 (2) | O5—C15—O6 | 125.6 (1) |
O3—C14—O4 | 124.3 (2) | O7—C17—O8 | 125.7 (2) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O3—H3···O1i | 1.08 (3) | 1.40 (3) | 2.481 (2) | 174 (3) |
O5—H5···O7 | 1.19 (3) | 1.26 (3) | 2.445 (2) | 175 (4) |
N9—H9···O2ii | 0.90 (2) | 1.81 (2) | 2.708 (2) | 170 (2) |
N10—H10···O8 | 0.87 (2) | 1.92 (2) | 2.781 (2) | 173 (2) |
Symmetry codes: (i) x, y, z−1; (ii) −x+1, −y, −z+2. |
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The crystal structures of the ammonium and isopropylammonium salts of the fumaric acid dianion were reported by Hosomi et al. (1998). In the title crystals, (I), trans–cis photoisomerization was observed, but no photodimerization occurred. There is a strong O5—H5···O7 hydrogen bond; the O5—H5 and O7—H5 distances are 1.19 (3) and 1.26 (3) Å, respectively.