In the title four compounds, C13H11N·C7H4N2O6, (I), C15H15N·C7H4N2O6, (II), C16H17N·C7H4N2O6, (III), and C16H17N·C7H4N2O6, (IV), the donor and acceptor molecules are stacked alternately to form one-dimensional columns. In (I), the N-methyl group of the donor is nearly eclipsed with respect to one of the nitro groups of the neighboring acceptor in a column, whereas the N-isopropyl, N-butyl and N-isobutyl groups are in anti positions with respect to one of the nitro groups of the neighboring acceptor in compounds (II)-(IV).
Supporting information
CCDC references: 144701; 144702; 144703; 144704
Equimolar mixtures of N-alkylcarbazoles and 3,5-dinitrobenzoic acid were
recrystallized from ethylacetate [for (I)], acetonitrile [for (II)–(III)] and
acetone [for (IV)].
In compounds (I)–(IV), the 3,5-dinitrobenzoic acid molecules form a dimeric
structure with cyclic hydrogen bonds. The acid proton has two possible
positions with site-occupation factors of 50%. They were located from
difference syntheses and refined isotropically. The O—H bond lengths are
0.73 (5)–0.88 (5) Å for (I), 0.78 (4)–0.82 (4) Å for (II), 0.64 (7)–1.01 (8) Å for (III) and 0.80 (6)–0.90 (8) Å for (IV). The other H-atom positional
parameters were calculated geometrically and fixed with Uiso(H) =
1.2Ueq(parent atom).
For all 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: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); software used to prepare material for publication: TEXSAN.
Crystal data top
C13H11N·C7H4N2O6 | Z = 2 |
Mr = 393.36 | Dx = 1.446 Mg m−3 |
Triclinic, P1 | Mo Kα radiation, λ = 0.71073 Å |
a = 8.414 (1) Å | Cell parameters from 25 reflections |
b = 15.763 (2) Å | θ = 14.8–15.0° |
c = 6.991 (1) Å | µ = 0.11 mm−1 |
α = 91.82 (1)° | T = 298 K |
β = 99.91 (1)° | Plate-like, orange |
γ = 81.59 (1)° | 0.6 × 0.4 × 0.1 mm |
V = 903.6 (2) Å3 | |
Data collection top
Rigaku AFC-7R diffractometer | θmax = 27.5°, θmin = 2.5° |
θ–2θ scans | h = −6→11 |
5045 measured reflections | k = −20→20 |
4128 independent reflections | l = −9→9 |
2977 reflections with I > 2σ(I) | 3 standard reflections every 150 reflections |
Rint = 0.005 | intensity decay: none |
Refinement top
Refinement on F2 | H atoms treated by a mixture of independent and constrained refinement |
R[F2 > 2σ(F2)] = 0.044 | w = 1/[σ2(Fo2) + (0.0715P)2 + 0.1508P] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.147 | (Δ/σ)max = 0.001 |
S = 1.08 | Δρmax = 0.29 e Å−3 |
4128 reflections | Δρmin = −0.18 e Å−3 |
270 parameters | |
Crystal data top
C13H11N·C7H4N2O6 | γ = 81.59 (1)° |
Mr = 393.36 | V = 903.6 (2) Å3 |
Triclinic, P1 | Z = 2 |
a = 8.414 (1) Å | Mo Kα radiation |
b = 15.763 (2) Å | µ = 0.11 mm−1 |
c = 6.991 (1) Å | T = 298 K |
α = 91.82 (1)° | 0.6 × 0.4 × 0.1 mm |
β = 99.91 (1)° | |
Data collection top
Rigaku AFC-7R diffractometer | Rint = 0.005 |
5045 measured reflections | 3 standard reflections every 150 reflections |
4128 independent reflections | intensity decay: none |
2977 reflections with I > 2σ(I) | |
Refinement top
R[F2 > 2σ(F2)] = 0.044 | 270 parameters |
wR(F2) = 0.147 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.08 | Δρmax = 0.29 e Å−3 |
4128 reflections | Δρmin = −0.18 e Å−3 |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | Occ. (<1) |
O1 | 0.3140 (2) | 0.54272 (9) | 0.3736 (2) | 0.0704 (4) | |
O2 | 0.5349 (2) | 0.60566 (9) | 0.4766 (2) | 0.0710 (4) | |
O3 | 0.5136 (2) | 0.90733 (9) | 0.3326 (3) | 0.0834 (4) | |
O4 | 0.2827 (2) | 0.98623 (8) | 0.2436 (2) | 0.0822 (4) | |
O5 | −0.2015 (2) | 0.8524 (1) | 0.0584 (3) | 0.0887 (5) | |
O6 | −0.1918 (2) | 0.7173 (1) | 0.1029 (3) | 0.0908 (5) | |
N7 | 0.3667 (2) | 0.91724 (9) | 0.2839 (2) | 0.0596 (4) | |
N8 | −0.1284 (2) | 0.7826 (1) | 0.1113 (2) | 0.0635 (4) | |
N9 | −0.0120 (2) | 0.7610 (1) | −0.3163 (2) | 0.0611 (4) | |
C10 | 0.3879 (2) | 0.6073 (1) | 0.3959 (2) | 0.0541 (4) | |
C11 | 0.2954 (2) | 0.6914 (1) | 0.3249 (2) | 0.0490 (3) | |
C12 | 0.3735 (2) | 0.7634 (1) | 0.3352 (2) | 0.0493 (3) | |
C13 | 0.2834 (2) | 0.8407 (1) | 0.2723 (2) | 0.0487 (3) | |
C14 | 0.1193 (2) | 0.8496 (1) | 0.1991 (2) | 0.0507 (4) | |
C15 | 0.0465 (2) | 0.7761 (1) | 0.1896 (2) | 0.0498 (4) | |
C16 | 0.1307 (2) | 0.6974 (1) | 0.2502 (2) | 0.0506 (4) | |
C17 | 0.1087 (2) | 0.8131 (1) | −0.2849 (2) | 0.0524 (4) | |
C18 | 0.0977 (2) | 0.9014 (1) | −0.3100 (3) | 0.0688 (5) | |
C19 | 0.2411 (3) | 0.9368 (1) | −0.2651 (3) | 0.0806 (6) | |
C20 | 0.3892 (3) | 0.8878 (2) | −0.1986 (3) | 0.0795 (6) | |
C21 | 0.3991 (2) | 0.8016 (1) | −0.1730 (3) | 0.0665 (5) | |
C22 | 0.2587 (2) | 0.7628 (1) | −0.2161 (2) | 0.0512 (4) | |
C23 | 0.2270 (2) | 0.6762 (1) | −0.2055 (2) | 0.0559 (4) | |
C24 | 0.3221 (3) | 0.5983 (2) | −0.1466 (3) | 0.0809 (6) | |
C25 | 0.2462 (5) | 0.5255 (2) | −0.1544 (4) | 0.1098 (10) | |
C26 | 0.0810 (5) | 0.5293 (2) | −0.2188 (5) | 0.117 (1) | |
C27 | −0.0156 (3) | 0.6041 (2) | −0.2773 (4) | 0.0922 (7) | |
C28 | 0.0583 (2) | 0.6780 (1) | −0.2692 (3) | 0.0615 (4) | |
C29 | −0.1823 (2) | 0.7891 (2) | −0.3917 (3) | 0.0859 (7) | |
H1 | 0.351 (6) | 0.503 (3) | 0.424 (6) | 0.0696 (2)* | 0.50 |
H2 | 0.585 (6) | 0.557 (4) | 0.528 (7) | 0.0809 (2)* | 0.50 |
H12 | 0.4884 | 0.7593 | 0.3855 | 0.0561* | |
H14 | 0.0576 | 0.9047 | 0.1564 | 0.0574* | |
H16 | 0.0760 | 0.6478 | 0.2416 | 0.0572* | |
H18 | −0.0056 | 0.9369 | −0.3543 | 0.0788* | |
H19 | 0.2351 | 0.9987 | −0.2832 | 0.0934* | |
H20 | 0.4882 | 0.9151 | −0.1656 | 0.0920* | |
H21 | 0.5029 | 0.7665 | −0.1286 | 0.0738* | |
H24 | 0.4370 | 0.5938 | −0.1008 | 0.0910* | |
H25 | 0.3043 | 0.4699 | −0.1197 | 0.1273* | |
H26 | 0.0335 | 0.4763 | −0.2168 | 0.1279* | |
H27 | −0.1311 | 0.6052 | −0.3223 | 0.1088* | |
H29A | −0.2417 | 0.7402 | −0.4013 | 0.0986* | |
H29B | −0.1942 | 0.8131 | −0.5184 | 0.0986* | |
H29C | −0.2280 | 0.8309 | −0.3061 | 0.0986* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O1 | 0.0756 (9) | 0.0456 (7) | 0.0824 (9) | −0.0108 (6) | −0.0118 (7) | 0.0115 (6) |
O2 | 0.0556 (7) | 0.0527 (7) | 0.097 (1) | −0.0010 (6) | −0.0056 (7) | 0.0145 (7) |
O3 | 0.0602 (8) | 0.0673 (9) | 0.122 (1) | −0.0201 (7) | 0.0028 (8) | 0.0144 (8) |
O4 | 0.0793 (9) | 0.0466 (7) | 0.119 (1) | −0.0067 (6) | 0.0124 (8) | 0.0136 (7) |
O5 | 0.0586 (8) | 0.0788 (10) | 0.114 (1) | 0.0117 (7) | −0.0080 (8) | 0.0024 (9) |
O6 | 0.0591 (8) | 0.084 (1) | 0.124 (1) | −0.0210 (8) | −0.0084 (8) | 0.0036 (9) |
N7 | 0.0620 (9) | 0.0497 (8) | 0.0684 (9) | −0.0112 (7) | 0.0106 (7) | 0.0065 (6) |
N8 | 0.0502 (8) | 0.0675 (10) | 0.0681 (9) | −0.0030 (7) | 0.0021 (7) | −0.0017 (7) |
N9 | 0.0372 (7) | 0.079 (1) | 0.0664 (9) | −0.0127 (7) | 0.0037 (6) | −0.0023 (7) |
C10 | 0.0550 (9) | 0.0467 (8) | 0.0570 (9) | −0.0054 (7) | 0.0000 (7) | 0.0038 (7) |
C11 | 0.0521 (8) | 0.0456 (8) | 0.0463 (8) | −0.0033 (6) | 0.0027 (6) | 0.0029 (6) |
C12 | 0.0472 (8) | 0.0490 (8) | 0.0499 (8) | −0.0060 (6) | 0.0034 (6) | 0.0036 (6) |
C13 | 0.0530 (8) | 0.0454 (8) | 0.0481 (8) | −0.0075 (6) | 0.0083 (6) | 0.0034 (6) |
C14 | 0.0530 (9) | 0.0475 (8) | 0.0487 (8) | 0.0012 (7) | 0.0074 (6) | 0.0035 (6) |
C15 | 0.0446 (8) | 0.0539 (9) | 0.0481 (8) | −0.0034 (7) | 0.0033 (6) | 0.0000 (6) |
C16 | 0.0532 (8) | 0.0467 (8) | 0.0508 (8) | −0.0093 (7) | 0.0038 (7) | −0.0003 (6) |
C17 | 0.0446 (8) | 0.0635 (10) | 0.0501 (8) | −0.0086 (7) | 0.0107 (6) | −0.0046 (7) |
C18 | 0.072 (1) | 0.065 (1) | 0.069 (1) | 0.0006 (9) | 0.0174 (9) | −0.0016 (9) |
C19 | 0.105 (2) | 0.067 (1) | 0.083 (1) | −0.035 (1) | 0.034 (1) | −0.015 (1) |
C20 | 0.075 (1) | 0.097 (2) | 0.078 (1) | −0.043 (1) | 0.021 (1) | −0.020 (1) |
C21 | 0.0454 (9) | 0.096 (1) | 0.061 (1) | −0.0208 (9) | 0.0100 (7) | −0.0121 (10) |
C22 | 0.0409 (8) | 0.068 (1) | 0.0453 (8) | −0.0097 (7) | 0.0085 (6) | −0.0052 (7) |
C23 | 0.0551 (9) | 0.064 (1) | 0.0483 (8) | −0.0067 (8) | 0.0105 (7) | −0.0004 (7) |
C24 | 0.090 (1) | 0.082 (1) | 0.064 (1) | 0.010 (1) | 0.013 (1) | 0.008 (1) |
C25 | 0.170 (3) | 0.064 (1) | 0.096 (2) | 0.002 (2) | 0.036 (2) | 0.016 (1) |
C26 | 0.165 (3) | 0.080 (2) | 0.121 (2) | −0.050 (2) | 0.038 (2) | −0.001 (2) |
C27 | 0.102 (2) | 0.094 (2) | 0.094 (2) | −0.052 (2) | 0.024 (1) | −0.010 (1) |
C28 | 0.062 (1) | 0.072 (1) | 0.0558 (9) | −0.0236 (9) | 0.0142 (8) | −0.0049 (8) |
C29 | 0.0434 (9) | 0.133 (2) | 0.077 (1) | −0.011 (1) | 0.0001 (9) | −0.004 (1) |
Geometric parameters (Å, º) top
O1—C10 | 1.260 (2) | C17—C22 | 1.406 (2) |
O1—H1 | 0.73 (5) | C18—C19 | 1.385 (3) |
O2—C10 | 1.265 (2) | C18—H18 | 0.970 |
O2—H2 | 0.88 (5) | C19—C20 | 1.382 (3) |
O3—N7 | 1.213 (2) | C19—H19 | 0.980 |
O4—N7 | 1.220 (2) | C20—C21 | 1.363 (3) |
O5—N8 | 1.214 (2) | C20—H20 | 0.982 |
O6—N8 | 1.222 (2) | C21—C22 | 1.393 (3) |
N7—C13 | 1.474 (2) | C21—H21 | 0.970 |
N8—C15 | 1.469 (2) | C22—C23 | 1.435 (3) |
N9—C17 | 1.382 (2) | C23—C24 | 1.395 (3) |
N9—C28 | 1.379 (2) | C23—C28 | 1.409 (2) |
N9—C29 | 1.449 (2) | C24—C25 | 1.388 (4) |
C10—C11 | 1.489 (2) | C24—H24 | 0.958 |
C11—C12 | 1.386 (2) | C25—C26 | 1.379 (6) |
C11—C16 | 1.385 (2) | C25—H25 | 0.957 |
C12—C13 | 1.379 (2) | C26—C27 | 1.362 (4) |
C12—H12 | 0.964 | C26—H26 | 0.979 |
C13—C14 | 1.376 (2) | C27—C28 | 1.394 (4) |
C14—C15 | 1.381 (2) | C27—H27 | 0.966 |
C14—H14 | 0.973 | C29—H29A | 0.972 |
C15—C16 | 1.376 (2) | C29—H29B | 0.958 |
C16—H16 | 0.960 | C29—H29C | 0.959 |
C17—C18 | 1.397 (3) | | |
| | | |
C10—O1—H1 | 120 (4) | C19—C18—H18 | 121.2 |
C10—O2—H2 | 116 (3) | C18—C19—C20 | 122.2 (2) |
O3—N7—O4 | 124.5 (2) | C18—C19—H19 | 117.8 |
O3—N7—C13 | 117.9 (1) | C20—C19—H19 | 120.1 |
O4—N7—C13 | 117.6 (1) | C19—C20—C21 | 120.6 (2) |
O5—N8—O6 | 123.8 (2) | C19—C20—H20 | 120.1 |
O5—N8—C15 | 118.2 (2) | C21—C20—H20 | 119.3 |
O6—N8—C15 | 118.0 (1) | C20—C21—C22 | 119.6 (2) |
C17—N9—C28 | 108.5 (1) | C20—C21—H21 | 121.2 |
C17—N9—C29 | 125.3 (2) | C22—C21—H21 | 119.2 |
C28—N9—C29 | 126.2 (2) | C17—C22—C21 | 119.4 (2) |
O1—C10—O2 | 124.4 (1) | C17—C22—C23 | 107.0 (1) |
O1—C10—C11 | 117.8 (1) | C21—C22—C23 | 133.6 (1) |
O2—C10—C11 | 117.7 (2) | C22—C23—C24 | 134.7 (2) |
C10—C11—C12 | 120.2 (1) | C22—C23—C28 | 106.3 (1) |
C10—C11—C16 | 119.6 (2) | C24—C23—C28 | 119.0 (2) |
C12—C11—C16 | 120.2 (1) | C23—C24—C25 | 118.4 (2) |
C11—C12—C13 | 118.7 (1) | C23—C24—H24 | 122.2 |
C11—C12—H12 | 120.4 | C25—C24—H24 | 119.4 |
C13—C12—H12 | 120.9 | C24—C25—C26 | 121.3 (2) |
N7—C13—C12 | 118.6 (1) | C24—C25—H25 | 122.8 |
N7—C13—C14 | 118.6 (1) | C26—C25—H25 | 115.9 |
C12—C13—C14 | 122.9 (2) | C25—C26—C27 | 122.0 (3) |
C13—C14—C15 | 116.6 (1) | C25—C26—H26 | 117.6 |
C13—C14—H14 | 121.7 | C27—C26—H26 | 120.4 |
C15—C14—H14 | 121.7 | C26—C27—C28 | 117.6 (3) |
N8—C15—C14 | 118.4 (1) | C26—C27—H27 | 120.5 |
N8—C15—C16 | 118.8 (1) | C28—C27—H27 | 121.8 |
C14—C15—C16 | 122.9 (1) | N9—C28—C23 | 109.3 (2) |
C11—C16—C15 | 118.8 (2) | N9—C28—C27 | 128.9 (2) |
C11—C16—H16 | 120.6 | C23—C28—C27 | 121.8 (2) |
C15—C16—H16 | 120.6 | N9—C29—H29A | 109.3 |
N9—C17—C18 | 129.8 (1) | N9—C29—H29B | 110.4 |
N9—C17—C22 | 109.0 (1) | N9—C29—H29C | 110.2 |
C18—C17—C22 | 121.2 (2) | H29A—C29—H29B | 108.6 |
C17—C18—C19 | 117.0 (2) | H29A—C29—H29C | 108.5 |
C17—C18—H18 | 121.8 | H29B—C29—H29C | 109.7 |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1···O2i | 0.73 (5) | 1.92 (5) | 2.648 (2) | 172 (5) |
O2—H2···O1i | 0.88 (5) | 1.77 (5) | 2.648 (2) | 179 (5) |
Symmetry code: (i) −x+1, −y+1, −z+1. |
Crystal data top
C15H15N·C7H4N2O6 | Dx = 1.368 Mg m−3 |
Mr = 421.41 | Mo Kα radiation, λ = 0.71073 Å |
Monoclinic, P21/a | Cell parameters from 25 reflections |
a = 8.504 (2) Å | θ = 12.9–14.9° |
b = 29.533 (4) Å | µ = 0.10 mm−1 |
c = 8.568 (2) Å | T = 298 K |
β = 108.05 (2)° | Prism, orange |
V = 2045.8 (7) Å3 | 0.5 × 0.5 × 0.5 mm |
Z = 4 | |
Data collection top
Rigaku AFC-7R diffractometer | θmax = 27.5°, θmin = 2.5° |
ω scans | h = 0→11 |
4990 measured reflections | k = 0→38 |
4685 independent reflections | l = −11→11 |
3283 reflections with I > 2σ(I) | 3 standard reflections every 150 reflections |
Rint = 0.011 | intensity decay: none |
Refinement top
Refinement on F2 | H atoms treated by a mixture of independent and constrained refinement |
R[F2 > 2σ(F2)] = 0.041 | w = 1/[σ2(Fo2) + (0.0542P)2 + 0.4038P] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.122 | (Δ/σ)max = 0.001 |
S = 1.05 | Δρmax = 0.21 e Å−3 |
4685 reflections | Δρmin = −0.16 e Å−3 |
288 parameters | |
Crystal data top
C15H15N·C7H4N2O6 | V = 2045.8 (7) Å3 |
Mr = 421.41 | Z = 4 |
Monoclinic, P21/a | Mo Kα radiation |
a = 8.504 (2) Å | µ = 0.10 mm−1 |
b = 29.533 (4) Å | T = 298 K |
c = 8.568 (2) Å | 0.5 × 0.5 × 0.5 mm |
β = 108.05 (2)° | |
Data collection top
Rigaku AFC-7R diffractometer | Rint = 0.011 |
4990 measured reflections | 3 standard reflections every 150 reflections |
4685 independent reflections | intensity decay: none |
3283 reflections with I > 2σ(I) | |
Refinement top
R[F2 > 2σ(F2)] = 0.041 | 288 parameters |
wR(F2) = 0.122 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.05 | Δρmax = 0.21 e Å−3 |
4685 reflections | Δρmin = −0.16 e Å−3 |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | Occ. (<1) |
O1 | 0.0226 (2) | 0.04384 (4) | 0.8774 (2) | 0.0606 (3) | |
O2 | −0.1986 (2) | 0.00141 (4) | 0.8629 (2) | 0.0596 (3) | |
O3 | −0.7332 (2) | 0.04803 (7) | 0.4968 (2) | 0.0970 (5) | |
O4 | −0.7483 (2) | 0.10037 (6) | 0.3189 (2) | 0.1084 (6) | |
O5 | −0.2710 (2) | 0.19129 (5) | 0.3509 (2) | 0.0817 (4) | |
O6 | −0.0299 (2) | 0.16733 (5) | 0.4925 (2) | 0.0758 (4) | |
N7 | −0.6713 (2) | 0.07701 (6) | 0.4337 (2) | 0.0707 (4) | |
N8 | −0.1798 (2) | 0.16475 (5) | 0.4448 (2) | 0.0564 (4) | |
N9 | −0.1902 (2) | 0.15813 (4) | 0.9916 (2) | 0.0465 (3) | |
C10 | −0.1272 (2) | 0.03405 (5) | 0.8168 (2) | 0.0444 (3) | |
C11 | −0.2308 (2) | 0.06314 (5) | 0.6819 (2) | 0.0424 (3) | |
C12 | −0.3995 (2) | 0.05581 (5) | 0.6200 (2) | 0.0472 (3) | |
C13 | −0.4926 (2) | 0.08431 (6) | 0.4990 (2) | 0.0500 (4) | |
C14 | −0.4246 (2) | 0.12029 (5) | 0.4386 (2) | 0.0507 (4) | |
C15 | −0.2578 (2) | 0.12641 (5) | 0.5040 (2) | 0.0454 (3) | |
C16 | −0.1577 (2) | 0.09853 (5) | 0.6235 (2) | 0.0443 (3) | |
C17 | −0.3188 (2) | 0.17607 (5) | 0.8648 (2) | 0.0471 (4) | |
C18 | −0.3213 (2) | 0.21217 (6) | 0.7593 (2) | 0.0596 (4) | |
C19 | −0.4665 (3) | 0.22179 (6) | 0.6387 (3) | 0.0715 (6) | |
C20 | −0.6101 (3) | 0.19693 (8) | 0.6203 (3) | 0.0731 (6) | |
C21 | −0.6102 (2) | 0.16132 (7) | 0.7240 (2) | 0.0625 (5) | |
C22 | −0.4635 (2) | 0.15013 (6) | 0.8467 (2) | 0.0483 (4) | |
C23 | −0.4179 (2) | 0.11450 (5) | 0.9659 (2) | 0.0468 (4) | |
C24 | −0.5036 (2) | 0.07788 (6) | 1.0045 (2) | 0.0602 (4) | |
C25 | −0.4202 (3) | 0.04785 (6) | 1.1229 (3) | 0.0676 (5) | |
C26 | −0.2531 (3) | 0.05316 (6) | 1.2039 (2) | 0.0633 (5) | |
C27 | −0.1636 (2) | 0.08915 (6) | 1.1707 (2) | 0.0527 (4) | |
C28 | −0.2487 (2) | 0.11996 (5) | 1.0511 (2) | 0.0434 (3) | |
C29 | −0.0238 (2) | 0.17727 (6) | 1.0673 (2) | 0.0524 (4) | |
C30 | 0.0890 (2) | 0.16815 (6) | 0.9637 (2) | 0.0677 (5) | |
C31 | −0.0289 (2) | 0.22717 (7) | 1.1096 (2) | 0.0735 (6) | |
H1 | 0.080 (5) | 0.031 (1) | 0.952 (6) | 0.0560 (1)* | 0.50 |
H2 | −0.144 (5) | −0.013 (1) | 0.943 (5) | 0.0530 (1)* | 0.50 |
H12 | −0.4503 | 0.0307 | 0.6580 | 0.0528* | |
H14 | −0.4920 | 0.1396 | 0.3528 | 0.0566* | |
H16 | −0.0384 | 0.1035 | 0.6665 | 0.0491* | |
H18 | −0.2218 | 0.2296 | 0.7704 | 0.0669* | |
H19 | −0.4721 | 0.2463 | 0.5627 | 0.0785* | |
H20 | −0.7118 | 0.2047 | 0.5348 | 0.0838* | |
H21 | −0.7106 | 0.1444 | 0.7119 | 0.0694* | |
H24 | −0.6204 | 0.0741 | 0.9492 | 0.0671* | |
H25 | −0.4772 | 0.0219 | 1.1493 | 0.0762* | |
H26 | −0.1980 | 0.0316 | 1.2862 | 0.0685* | |
H27 | −0.0468 | 0.0922 | 1.2269 | 0.0583* | |
H29 | 0.0242 | 0.1619 | 1.1712 | 0.0560* | |
H30A | 0.1966 | 0.1807 | 1.0164 | 0.0764* | |
H30B | 0.0426 | 0.1818 | 0.8580 | 0.0764* | |
H30C | 0.0984 | 0.1360 | 0.9512 | 0.0764* | |
H31A | −0.0823 | 0.2441 | 1.0094 | 0.0825* | |
H31B | 0.0793 | 0.2390 | 1.1585 | 0.0825* | |
H31C | −0.0939 | 0.2315 | 1.1832 | 0.0825* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O1 | 0.0483 (7) | 0.0612 (8) | 0.0639 (8) | 0.0032 (6) | 0.0051 (6) | 0.0221 (6) |
O2 | 0.0602 (7) | 0.0528 (7) | 0.0599 (7) | −0.0017 (6) | 0.0102 (6) | 0.0206 (6) |
O3 | 0.0576 (9) | 0.116 (1) | 0.109 (1) | −0.0145 (9) | 0.0134 (9) | 0.019 (1) |
O4 | 0.0598 (9) | 0.111 (1) | 0.124 (1) | 0.0116 (9) | −0.0173 (9) | 0.036 (1) |
O5 | 0.108 (1) | 0.0617 (8) | 0.0807 (9) | 0.0196 (8) | 0.0365 (9) | 0.0353 (7) |
O6 | 0.0753 (10) | 0.0687 (9) | 0.0779 (9) | −0.0199 (7) | 0.0160 (8) | 0.0140 (7) |
N7 | 0.0499 (9) | 0.074 (1) | 0.077 (1) | 0.0049 (8) | 0.0033 (8) | 0.0019 (9) |
N8 | 0.083 (1) | 0.0422 (7) | 0.0457 (7) | 0.0028 (7) | 0.0228 (7) | 0.0050 (6) |
N9 | 0.0425 (7) | 0.0443 (7) | 0.0542 (7) | −0.0099 (5) | 0.0173 (6) | −0.0018 (6) |
C10 | 0.0481 (9) | 0.0409 (8) | 0.0435 (8) | 0.0037 (6) | 0.0130 (7) | 0.0051 (6) |
C11 | 0.0490 (8) | 0.0377 (7) | 0.0395 (7) | 0.0050 (6) | 0.0124 (6) | 0.0014 (6) |
C12 | 0.0507 (9) | 0.0432 (8) | 0.0473 (8) | 0.0015 (7) | 0.0148 (7) | 0.0017 (7) |
C13 | 0.0461 (8) | 0.0515 (9) | 0.0477 (8) | 0.0077 (7) | 0.0077 (7) | −0.0025 (7) |
C14 | 0.062 (1) | 0.0451 (8) | 0.0415 (8) | 0.0136 (7) | 0.0102 (7) | 0.0045 (6) |
C15 | 0.0613 (10) | 0.0371 (7) | 0.0383 (7) | 0.0028 (7) | 0.0162 (7) | 0.0012 (6) |
C16 | 0.0510 (9) | 0.0396 (8) | 0.0407 (7) | 0.0025 (6) | 0.0120 (6) | 0.0010 (6) |
C17 | 0.0491 (9) | 0.0420 (8) | 0.0548 (9) | 0.0002 (7) | 0.0225 (7) | −0.0059 (7) |
C18 | 0.071 (1) | 0.0459 (9) | 0.067 (1) | 0.0034 (8) | 0.0292 (10) | 0.0017 (8) |
C19 | 0.091 (2) | 0.056 (1) | 0.071 (1) | 0.026 (1) | 0.029 (1) | 0.0080 (9) |
C20 | 0.068 (1) | 0.076 (1) | 0.071 (1) | 0.031 (1) | 0.014 (1) | −0.004 (1) |
C21 | 0.0446 (9) | 0.073 (1) | 0.070 (1) | 0.0091 (8) | 0.0181 (8) | −0.0151 (10) |
C22 | 0.0427 (8) | 0.0509 (9) | 0.0560 (9) | 0.0007 (7) | 0.0221 (7) | −0.0100 (7) |
C23 | 0.0459 (8) | 0.0475 (8) | 0.0529 (9) | −0.0094 (7) | 0.0239 (7) | −0.0124 (7) |
C24 | 0.061 (1) | 0.062 (1) | 0.067 (1) | −0.0234 (9) | 0.0325 (9) | −0.0154 (9) |
C25 | 0.095 (1) | 0.052 (1) | 0.070 (1) | −0.029 (1) | 0.045 (1) | −0.0120 (9) |
C26 | 0.098 (2) | 0.0448 (9) | 0.0548 (10) | −0.0073 (9) | 0.035 (1) | −0.0014 (8) |
C27 | 0.060 (1) | 0.0501 (9) | 0.0500 (9) | −0.0030 (8) | 0.0206 (8) | −0.0049 (7) |
C28 | 0.0477 (8) | 0.0407 (7) | 0.0467 (8) | −0.0084 (6) | 0.0220 (7) | −0.0080 (6) |
C29 | 0.0473 (9) | 0.0563 (9) | 0.0529 (9) | −0.0168 (7) | 0.0148 (7) | −0.0054 (7) |
C30 | 0.052 (1) | 0.075 (1) | 0.082 (1) | −0.0136 (9) | 0.0291 (9) | −0.013 (1) |
C31 | 0.078 (1) | 0.062 (1) | 0.086 (1) | −0.027 (1) | 0.034 (1) | −0.025 (1) |
Geometric parameters (Å, º) top
O1—C10 | 1.251 (2) | C19—C20 | 1.391 (3) |
O1—H1 | 0.78 (4) | C19—H19 | 0.966 |
O2—C10 | 1.266 (2) | C20—C21 | 1.377 (3) |
O2—H2 | 0.82 (4) | C20—H20 | 0.972 |
O3—N7 | 1.216 (3) | C21—C22 | 1.399 (2) |
O4—N7 | 1.214 (2) | C21—H21 | 0.967 |
O5—N8 | 1.215 (2) | C22—C23 | 1.433 (2) |
O6—N8 | 1.215 (2) | C23—C24 | 1.400 (3) |
N7—C13 | 1.463 (2) | C23—C28 | 1.407 (2) |
N8—C15 | 1.479 (2) | C24—C25 | 1.368 (3) |
N9—C17 | 1.387 (2) | C24—H24 | 0.965 |
N9—C28 | 1.391 (2) | C25—C26 | 1.384 (3) |
N9—C29 | 1.474 (2) | C25—H25 | 0.970 |
C10—C11 | 1.490 (2) | C26—C27 | 1.387 (3) |
C11—C12 | 1.383 (2) | C26—H26 | 0.958 |
C11—C16 | 1.386 (2) | C27—C28 | 1.394 (2) |
C12—C13 | 1.379 (2) | C27—H27 | 0.964 |
C12—H12 | 0.964 | C29—C30 | 1.518 (3) |
C13—C14 | 1.384 (3) | C29—C31 | 1.521 (3) |
C14—C15 | 1.366 (2) | C29—H29 | 0.971 |
C14—H14 | 0.966 | C30—H30A | 0.960 |
C15—C16 | 1.383 (2) | C30—H30B | 0.958 |
C16—H16 | 0.978 | C30—H30C | 0.961 |
C17—C18 | 1.393 (3) | C31—H31A | 0.976 |
C17—C22 | 1.417 (2) | C31—H31B | 0.951 |
C18—C19 | 1.372 (3) | C31—H31C | 0.967 |
C18—H18 | 0.969 | | |
| | | |
C10—O1—H1 | 122 (3) | C21—C20—H20 | 119.3 |
C10—O2—H2 | 118 (3) | C20—C21—C22 | 119.1 (2) |
O3—N7—O4 | 124.1 (2) | C20—C21—H21 | 120.2 |
O3—N7—C13 | 118.4 (2) | C22—C21—H21 | 120.6 |
O4—N7—C13 | 117.5 (2) | C17—C22—C21 | 119.7 (2) |
O5—N8—O6 | 124.8 (2) | C17—C22—C23 | 106.6 (1) |
O5—N8—C15 | 117.3 (2) | C21—C22—C23 | 133.6 (2) |
O6—N8—C15 | 117.9 (1) | C22—C23—C24 | 133.6 (1) |
C17—N9—C28 | 108.2 (1) | C22—C23—C28 | 107.0 (1) |
C17—N9—C29 | 128.0 (1) | C24—C23—C28 | 119.3 (1) |
C28—N9—C29 | 123.6 (1) | C23—C24—C25 | 119.2 (2) |
O1—C10—O2 | 124.8 (1) | C23—C24—H24 | 120.3 |
O1—C10—C11 | 118.1 (1) | C25—C24—H24 | 120.5 |
O2—C10—C11 | 117.1 (1) | C24—C25—C26 | 120.9 (2) |
C10—C11—C12 | 120.1 (1) | C24—C25—H25 | 120.2 |
C10—C11—C16 | 119.4 (1) | C26—C25—H25 | 118.8 |
C12—C11—C16 | 120.5 (1) | C25—C26—C27 | 121.8 (2) |
C11—C12—C13 | 118.6 (2) | C25—C26—H26 | 119.1 |
C11—C12—H12 | 120.7 | C27—C26—H26 | 119.1 |
C13—C12—H12 | 120.7 | C26—C27—C28 | 117.3 (1) |
N7—C13—C12 | 118.9 (2) | C26—C27—H27 | 121.0 |
N7—C13—C14 | 118.3 (1) | C28—C27—H27 | 121.7 |
C12—C13—C14 | 122.7 (1) | N9—C28—C23 | 109.1 (1) |
C13—C14—C15 | 116.7 (1) | N9—C28—C27 | 129.4 (1) |
C13—C14—H14 | 121.3 | C23—C28—C27 | 121.4 (1) |
C15—C14—H14 | 121.9 | N9—C29—C30 | 111.6 (1) |
N8—C15—C14 | 118.7 (1) | N9—C29—C31 | 112.4 (1) |
N8—C15—C16 | 118.1 (1) | N9—C29—H29 | 107.3 |
C14—C15—C16 | 123.2 (2) | C30—C29—C31 | 112.4 (2) |
C11—C16—C15 | 118.3 (1) | C30—C29—H29 | 106.9 |
C11—C16—H16 | 120.4 | C31—C29—H29 | 105.7 |
C15—C16—H16 | 121.3 | C29—C30—H30A | 109.8 |
N9—C17—C18 | 130.6 (2) | C29—C30—H30B | 109.1 |
N9—C17—C22 | 109.1 (1) | C29—C30—H30C | 109.3 |
C18—C17—C22 | 120.3 (1) | H30A—C30—H30B | 109.6 |
C17—C18—C19 | 118.4 (2) | H30A—C30—H30C | 109.4 |
C17—C18—H18 | 120.4 | H30B—C30—H30C | 109.6 |
C19—C18—H18 | 121.2 | C29—C31—H31A | 109.1 |
C18—C19—C20 | 122.0 (2) | C29—C31—H31B | 111.4 |
C18—C19—H19 | 120.5 | C29—C31—H31C | 110.3 |
C20—C19—H19 | 117.5 | H31A—C31—H31B | 108.8 |
C19—C20—C21 | 120.4 (2) | H31A—C31—H31C | 107.5 |
C19—C20—H20 | 120.4 | H31B—C31—H31C | 109.6 |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1···O2i | 0.78 (4) | 1.86 (4) | 2.629 (2) | 174 (5) |
O2—H2···O1i | 0.82 (4) | 1.81 (4) | 2.629 (2) | 178 (4) |
Symmetry code: (i) −x, −y, −z+2. |
Crystal data top
C16H17N·C7H4N2O6 | Z = 4 |
Mr = 435.44 | Dx = 1.344 Mg m−3 |
Triclinic, P1 | Mo Kα radiation, λ = 0.71073 Å |
a = 16.723 (2) Å | Cell parameters from 25 reflections |
b = 16.784 (3) Å | θ = 11.8–14.7° |
c = 8.4129 (9) Å | µ = 0.10 mm−1 |
α = 102.36 (1)° | T = 298 K |
β = 92.34 (1)° | Prism, orange |
γ = 109.91 (1)° | 0.6 × 0.5 × 0.2 mm |
V = 2152.0 (6) Å3 | |
Data collection top
Rigaku AFC-7R diffractometer | θmax = 27.5°, θmin = 2.5° |
θ–2θ scans | h = 0→22 |
10208 measured reflections | k = −22→22 |
9870 independent reflections | l = −11→11 |
4817 reflections with I > 2σ(I) | 3 standard reflections every 150 reflections |
Rint = 0.010 | intensity decay: none |
Refinement top
Refinement on F2 | H atoms treated by a mixture of independent and constrained refinement |
R[F2 > 2σ(F2)] = 0.061 | w = 1/[σ2(Fo2) + (0.050P)2] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.192 | (Δ/σ)max = 0.001 |
S = 1.74 | Δρmax = 0.24 e Å−3 |
9870 reflections | Δρmin = −0.25 e Å−3 |
593 parameters | |
Crystal data top
C16H17N·C7H4N2O6 | γ = 109.91 (1)° |
Mr = 435.44 | V = 2152.0 (6) Å3 |
Triclinic, P1 | Z = 4 |
a = 16.723 (2) Å | Mo Kα radiation |
b = 16.784 (3) Å | µ = 0.10 mm−1 |
c = 8.4129 (9) Å | T = 298 K |
α = 102.36 (1)° | 0.6 × 0.5 × 0.2 mm |
β = 92.34 (1)° | |
Data collection top
Rigaku AFC-7R diffractometer | Rint = 0.010 |
10208 measured reflections | 3 standard reflections every 150 reflections |
9870 independent reflections | intensity decay: none |
4817 reflections with I > 2σ(I) | |
Refinement top
R[F2 > 2σ(F2)] = 0.061 | 593 parameters |
wR(F2) = 0.192 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.74 | Δρmax = 0.24 e Å−3 |
9870 reflections | Δρmin = −0.25 e Å−3 |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | Occ. (<1) |
O1 | 0.1139 (2) | 0.3069 (2) | 0.8584 (3) | 0.0751 (8) | |
O1* | −0.0704 (1) | 0.2143 (1) | 0.5645 (3) | 0.0705 (6) | |
O2 | 0.0230 (2) | 0.1692 (1) | 0.7635 (3) | 0.0719 (6) | |
O2* | 0.0097 (1) | 0.3540 (1) | 0.6844 (3) | 0.0665 (5) | |
O3 | 0.0840 (2) | −0.0625 (2) | 0.9435 (4) | 0.125 (1) | |
O3* | −0.1002 (2) | 0.5786 (1) | 0.6063 (3) | 0.0879 (7) | |
O4 | 0.1969 (2) | −0.0341 (2) | 1.1044 (4) | 0.123 (1) | |
O4* | −0.1979 (2) | 0.5499 (1) | 0.4060 (3) | 0.1023 (8) | |
O5 | 0.4042 (2) | 0.2571 (2) | 1.2670 (3) | 0.0994 (8) | |
O5* | −0.3542 (2) | 0.2507 (2) | 0.1185 (3) | 0.0964 (7) | |
O6 | 0.3728 (2) | 0.3626 (2) | 1.2126 (3) | 0.1074 (8) | |
O6* | −0.3153 (2) | 0.1498 (2) | 0.1733 (3) | 0.0997 (8) | |
N7 | 0.1496 (2) | −0.0125 (2) | 1.0244 (4) | 0.0814 (8) | |
N7* | −0.1524 (2) | 0.5285 (2) | 0.4910 (3) | 0.0695 (6) | |
N8 | 0.3570 (2) | 0.2854 (2) | 1.2035 (3) | 0.0746 (7) | |
N8* | −0.3070 (2) | 0.2259 (2) | 0.1906 (3) | 0.0692 (6) | |
N9 | 0.3086 (2) | 0.2507 (2) | 0.6347 (3) | 0.0702 (7) | |
N9* | −0.2725 (1) | 0.2366 (1) | 0.7314 (3) | 0.0609 (6) | |
C10 | 0.0895 (2) | 0.2252 (2) | 0.8477 (3) | 0.0571 (7) | |
C10* | −0.0521 (2) | 0.2969 (2) | 0.5896 (3) | 0.0540 (6) | |
C11 | 0.1462 (2) | 0.1957 (2) | 0.9426 (3) | 0.0522 (6) | |
C11* | −0.1120 (2) | 0.3247 (2) | 0.4983 (3) | 0.0505 (6) | |
C12 | 0.1219 (2) | 0.1080 (2) | 0.9414 (3) | 0.0556 (6) | |
C12* | −0.1029 (2) | 0.4123 (2) | 0.5331 (3) | 0.0515 (6) | |
C13 | 0.1753 (2) | 0.0811 (2) | 1.0266 (3) | 0.0583 (7) | |
C13* | −0.1608 (2) | 0.4366 (2) | 0.4509 (3) | 0.0536 (6) | |
C14 | 0.2533 (2) | 0.1369 (2) | 1.1121 (3) | 0.0581 (7) | |
C14* | −0.2269 (2) | 0.3776 (2) | 0.3358 (3) | 0.0550 (6) | |
C15 | 0.2748 (2) | 0.2232 (2) | 1.1109 (3) | 0.0542 (6) | |
C15* | −0.2339 (2) | 0.2919 (2) | 0.3068 (3) | 0.0546 (6) | |
C16 | 0.2228 (2) | 0.2540 (2) | 1.0285 (3) | 0.0559 (6) | |
C16* | −0.1785 (2) | 0.2632 (2) | 0.3839 (3) | 0.0541 (6) | |
C17 | 0.3370 (2) | 0.1947 (2) | 0.7003 (4) | 0.0686 (8) | |
C17* | −0.3080 (2) | 0.2944 (2) | 0.6928 (3) | 0.0637 (7) | |
C18 | 0.4137 (2) | 0.2124 (2) | 0.7987 (4) | 0.089 (1) | |
C18* | −0.3799 (2) | 0.2763 (2) | 0.5781 (4) | 0.087 (1) | |
C19 | 0.4264 (2) | 0.1463 (4) | 0.8528 (5) | 0.106 (1) | |
C19* | −0.3987 (2) | 0.3483 (4) | 0.5592 (5) | 0.115 (2) | |
C20 | 0.3643 (4) | 0.0633 (3) | 0.8107 (5) | 0.108 (1) | |
C20* | −0.3521 (4) | 0.4326 (4) | 0.6504 (7) | 0.127 (2) | |
C21 | 0.2882 (3) | 0.0435 (2) | 0.7125 (4) | 0.088 (1) | |
C21* | −0.2842 (3) | 0.4492 (2) | 0.7628 (4) | 0.097 (1) | |
C22 | 0.2742 (2) | 0.1114 (2) | 0.6555 (4) | 0.0659 (8) | |
C22* | −0.2596 (2) | 0.3792 (2) | 0.7852 (4) | 0.0673 (8) | |
C23 | 0.2056 (2) | 0.1170 (2) | 0.5561 (3) | 0.0673 (8) | |
C23* | −0.1928 (2) | 0.3717 (2) | 0.8863 (3) | 0.0614 (7) | |
C24 | 0.1276 (3) | 0.0583 (2) | 0.4748 (4) | 0.094 (1) | |
C24* | −0.1249 (3) | 0.4329 (2) | 0.9997 (4) | 0.087 (1) | |
C25 | 0.0752 (2) | 0.0857 (4) | 0.3898 (5) | 0.111 (1) | |
C25* | −0.0700 (2) | 0.4025 (3) | 1.0729 (4) | 0.102 (1) | |
C26 | 0.0980 (3) | 0.1716 (4) | 0.3830 (4) | 0.108 (1) | |
C26* | −0.0812 (2) | 0.3143 (3) | 1.0379 (4) | 0.093 (1) | |
C27 | 0.1752 (3) | 0.2338 (2) | 0.4602 (4) | 0.0814 (9) | |
C27* | −0.1475 (2) | 0.2521 (2) | 0.9265 (4) | 0.0700 (8) | |
C28 | 0.2288 (2) | 0.2047 (2) | 0.5461 (3) | 0.0646 (7) | |
C28* | −0.2027 (2) | 0.2831 (2) | 0.8504 (3) | 0.0562 (7) | |
C29 | 0.3612 (2) | 0.3412 (2) | 0.6392 (4) | 0.090 (1) | |
C29* | −0.3014 (2) | 0.1437 (2) | 0.6573 (4) | 0.0724 (8) | |
C30 | 0.3591 (2) | 0.4080 (2) | 0.7868 (3) | 0.0679 (8) | |
C30* | −0.3724 (2) | 0.0888 (2) | 0.7351 (4) | 0.0747 (9) | |
C31 | 0.4133 (2) | 0.4993 (2) | 0.7712 (4) | 0.0835 (9) | |
C31* | −0.3984 (2) | −0.0080 (2) | 0.6605 (4) | 0.0860 (10) | |
C32 | 0.4164 (2) | 0.5697 (2) | 0.9123 (4) | 0.104 (1) | |
C32* | −0.4633 (3) | −0.0640 (2) | 0.7417 (5) | 0.116 (1) | |
H1 | 0.092 (4) | 0.323 (4) | 0.820 (7) | 0.0343 (2)* | 0.50 |
H1* | −0.034 (3) | 0.196 (3) | 0.606 (7) | 0.0470 (2)* | 0.50 |
H2 | −0.007 (4) | 0.182 (4) | 0.716 (9) | 0.0661 (3)* | 0.50 |
H2* | 0.044 (5) | 0.330 (4) | 0.750 (8) | 0.0931 (3)* | 0.50 |
H12 | 0.0680 | 0.0660 | 0.8816 | 0.0662* | |
H12* | −0.0564 | 0.4562 | 0.6123 | 0.0589* | |
H14 | 0.2910 | 0.1165 | 1.1703 | 0.0675* | |
H14* | −0.2657 | 0.3970 | 0.2790 | 0.0629* | |
H16 | 0.2412 | 0.3165 | 1.0317 | 0.0645* | |
H16* | −0.1856 | 0.2011 | 0.3593 | 0.0616* | |
H18 | 0.4568 | 0.2720 | 0.8263 | 0.1002* | |
H18* | −0.4147 | 0.2167 | 0.5172 | 0.1043* | |
H19 | 0.4800 | 0.1572 | 0.9203 | 0.1203* | |
H19* | −0.4462 | 0.3411 | 0.4812 | 0.1297* | |
H20 | 0.3748 | 0.0187 | 0.8538 | 0.1320* | |
H20* | −0.3685 | 0.4798 | 0.6278 | 0.1407* | |
H21 | 0.2461 | −0.0149 | 0.6859 | 0.1027* | |
H21* | −0.2532 | 0.5081 | 0.8263 | 0.1150* | |
H24 | 0.1084 | −0.0031 | 0.4780 | 0.1099* | |
H24* | −0.1187 | 0.4946 | 1.0278 | 0.1026* | |
H25 | 0.0213 | 0.0441 | 0.3309 | 0.1259* | |
H25* | −0.0219 | 0.4438 | 1.1492 | 0.1232* | |
H26 | 0.0603 | 0.1898 | 0.3203 | 0.1279* | |
H26* | −0.0411 | 0.2961 | 1.0937 | 0.1085* | |
H27 | 0.1925 | 0.2955 | 0.4571 | 0.0975* | |
H27* | −0.1550 | 0.1903 | 0.9014 | 0.0827* | |
H29A | 0.3419 | 0.3563 | 0.5429 | 0.1049* | |
H29B | 0.4198 | 0.3449 | 0.6328 | 0.1049* | |
H29*A | −0.2532 | 0.1254 | 0.6659 | 0.0873* | |
H29*B | −0.3205 | 0.1350 | 0.5432 | 0.0873* | |
H30A | 0.3017 | 0.4054 | 0.7978 | 0.0772* | |
H30B | 0.3828 | 0.3978 | 0.8840 | 0.0772* | |
H30*A | −0.3561 | 0.1003 | 0.8508 | 0.0843* | |
H30*B | −0.4233 | 0.1047 | 0.7207 | 0.0843* | |
H31A | 0.3898 | 0.5091 | 0.6734 | 0.0933* | |
H31B | 0.4710 | 0.5012 | 0.7581 | 0.0933* | |
H31*A | −0.3469 | −0.0228 | 0.6653 | 0.0978* | |
H31*B | −0.4196 | −0.0202 | 0.5451 | 0.0978* | |
H32A | 0.4513 | 0.6253 | 0.8958 | 0.1152* | |
H32B | 0.4402 | 0.5608 | 1.0103 | 0.1152* | |
H32C | 0.3593 | 0.5692 | 0.9251 | 0.1152* | |
H32*B | −0.5156 | −0.0509 | 0.7358 | 0.1292* | |
H32*C | −0.4430 | −0.0528 | 0.8570 | 0.1292* | |
H32*A | −0.4772 | −0.1249 | 0.6923 | 0.1292* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O1 | 0.083 (2) | 0.072 (2) | 0.080 (2) | 0.036 (1) | −0.006 (1) | 0.028 (1) |
O1* | 0.079 (1) | 0.069 (1) | 0.074 (1) | 0.042 (1) | −0.004 (1) | 0.015 (1) |
O2 | 0.066 (1) | 0.074 (1) | 0.078 (2) | 0.028 (1) | −0.009 (1) | 0.021 (1) |
O2* | 0.060 (1) | 0.070 (1) | 0.070 (1) | 0.022 (1) | −0.005 (1) | 0.022 (1) |
O3 | 0.121 (2) | 0.067 (2) | 0.170 (3) | 0.014 (2) | −0.042 (2) | 0.034 (2) |
O3* | 0.102 (2) | 0.057 (1) | 0.090 (2) | 0.018 (1) | −0.015 (1) | 0.009 (1) |
O4 | 0.126 (2) | 0.078 (2) | 0.170 (3) | 0.043 (2) | −0.034 (2) | 0.042 (2) |
O4* | 0.095 (2) | 0.076 (2) | 0.142 (2) | 0.038 (1) | −0.023 (2) | 0.036 (1) |
O5 | 0.078 (2) | 0.112 (2) | 0.098 (2) | 0.034 (1) | −0.029 (1) | 0.010 (1) |
O5* | 0.080 (2) | 0.106 (2) | 0.089 (2) | 0.031 (1) | −0.030 (1) | 0.005 (1) |
O6 | 0.104 (2) | 0.081 (2) | 0.112 (2) | 0.005 (1) | −0.023 (2) | 0.023 (1) |
O6* | 0.104 (2) | 0.070 (2) | 0.094 (2) | 0.004 (1) | −0.022 (1) | 0.007 (1) |
N7 | 0.076 (2) | 0.064 (2) | 0.103 (2) | 0.025 (2) | −0.006 (2) | 0.023 (2) |
N7* | 0.068 (2) | 0.059 (2) | 0.083 (2) | 0.022 (1) | 0.003 (1) | 0.025 (1) |
N8 | 0.074 (2) | 0.079 (2) | 0.061 (2) | 0.019 (2) | −0.001 (1) | 0.012 (1) |
N8* | 0.060 (2) | 0.075 (2) | 0.056 (1) | 0.009 (1) | 0.000 (1) | 0.009 (1) |
N9 | 0.072 (2) | 0.058 (1) | 0.073 (2) | 0.015 (1) | 0.014 (1) | 0.015 (1) |
N9* | 0.059 (1) | 0.054 (1) | 0.059 (1) | 0.010 (1) | 0.008 (1) | 0.009 (1) |
C10 | 0.065 (2) | 0.062 (2) | 0.053 (2) | 0.030 (2) | 0.009 (1) | 0.018 (1) |
C10* | 0.060 (2) | 0.060 (2) | 0.049 (2) | 0.027 (1) | 0.009 (1) | 0.016 (1) |
C11 | 0.051 (2) | 0.064 (2) | 0.048 (1) | 0.026 (1) | 0.010 (1) | 0.016 (1) |
C11* | 0.050 (1) | 0.059 (2) | 0.046 (1) | 0.021 (1) | 0.009 (1) | 0.016 (1) |
C12 | 0.051 (2) | 0.056 (2) | 0.061 (2) | 0.020 (1) | 0.003 (1) | 0.015 (1) |
C12* | 0.048 (1) | 0.060 (2) | 0.045 (1) | 0.017 (1) | 0.004 (1) | 0.014 (1) |
C13 | 0.064 (2) | 0.052 (2) | 0.064 (2) | 0.025 (1) | 0.009 (1) | 0.017 (1) |
C13* | 0.054 (2) | 0.056 (2) | 0.055 (2) | 0.020 (1) | 0.011 (1) | 0.020 (1) |
C14 | 0.063 (2) | 0.067 (2) | 0.054 (2) | 0.033 (2) | 0.008 (1) | 0.016 (1) |
C14* | 0.046 (1) | 0.070 (2) | 0.053 (2) | 0.021 (1) | 0.006 (1) | 0.023 (1) |
C15 | 0.049 (2) | 0.064 (2) | 0.047 (1) | 0.019 (1) | 0.005 (1) | 0.010 (1) |
C15* | 0.046 (1) | 0.071 (2) | 0.041 (1) | 0.014 (1) | 0.007 (1) | 0.014 (1) |
C16 | 0.062 (2) | 0.061 (2) | 0.048 (1) | 0.023 (1) | 0.013 (1) | 0.016 (1) |
C16* | 0.061 (2) | 0.060 (2) | 0.045 (1) | 0.024 (1) | 0.013 (1) | 0.016 (1) |
C17 | 0.072 (2) | 0.070 (2) | 0.063 (2) | 0.027 (2) | 0.021 (2) | 0.010 (2) |
C17* | 0.056 (2) | 0.079 (2) | 0.059 (2) | 0.023 (2) | 0.018 (1) | 0.021 (2) |
C18 | 0.073 (2) | 0.116 (3) | 0.080 (2) | 0.039 (2) | 0.018 (2) | 0.017 (2) |
C18* | 0.061 (2) | 0.131 (3) | 0.077 (2) | 0.037 (2) | 0.015 (2) | 0.036 (2) |
C19 | 0.095 (3) | 0.147 (4) | 0.096 (3) | 0.073 (3) | 0.020 (2) | 0.021 (3) |
C19* | 0.090 (3) | 0.207 (5) | 0.096 (3) | 0.089 (4) | 0.038 (2) | 0.074 (3) |
C20 | 0.147 (4) | 0.136 (4) | 0.090 (3) | 0.104 (4) | 0.040 (3) | 0.032 (3) |
C20* | 0.161 (5) | 0.191 (5) | 0.116 (4) | 0.132 (5) | 0.080 (4) | 0.091 (4) |
C21 | 0.122 (3) | 0.071 (2) | 0.084 (2) | 0.047 (2) | 0.045 (2) | 0.016 (2) |
C21* | 0.143 (4) | 0.091 (3) | 0.098 (3) | 0.070 (3) | 0.069 (3) | 0.050 (2) |
C22 | 0.077 (2) | 0.060 (2) | 0.061 (2) | 0.029 (2) | 0.023 (2) | 0.008 (1) |
C22* | 0.082 (2) | 0.068 (2) | 0.060 (2) | 0.031 (2) | 0.032 (2) | 0.022 (2) |
C23 | 0.075 (2) | 0.060 (2) | 0.054 (2) | 0.016 (2) | 0.021 (2) | −0.001 (1) |
C23* | 0.075 (2) | 0.050 (2) | 0.049 (2) | 0.008 (1) | 0.022 (1) | 0.010 (1) |
C24 | 0.094 (3) | 0.082 (2) | 0.076 (2) | 0.006 (2) | 0.023 (2) | −0.001 (2) |
C24* | 0.096 (3) | 0.073 (2) | 0.058 (2) | −0.008 (2) | 0.021 (2) | 0.004 (2) |
C25 | 0.081 (3) | 0.147 (4) | 0.067 (2) | 0.011 (3) | 0.003 (2) | −0.005 (3) |
C25* | 0.079 (3) | 0.127 (3) | 0.049 (2) | −0.018 (2) | 0.010 (2) | 0.008 (2) |
C26 | 0.100 (3) | 0.176 (5) | 0.058 (2) | 0.066 (3) | 0.014 (2) | 0.018 (3) |
C26* | 0.063 (2) | 0.150 (4) | 0.058 (2) | 0.019 (2) | 0.007 (2) | 0.038 (2) |
C27 | 0.098 (3) | 0.100 (3) | 0.063 (2) | 0.052 (2) | 0.025 (2) | 0.024 (2) |
C27* | 0.071 (2) | 0.085 (2) | 0.059 (2) | 0.026 (2) | 0.019 (2) | 0.030 (2) |
C28 | 0.073 (2) | 0.063 (2) | 0.054 (2) | 0.021 (2) | 0.019 (2) | 0.008 (1) |
C28* | 0.053 (2) | 0.060 (2) | 0.048 (2) | 0.009 (1) | 0.013 (1) | 0.015 (1) |
C29 | 0.105 (3) | 0.065 (2) | 0.084 (2) | 0.009 (2) | 0.032 (2) | 0.019 (2) |
C29* | 0.075 (2) | 0.059 (2) | 0.065 (2) | 0.007 (2) | 0.011 (2) | 0.004 (1) |
C30 | 0.071 (2) | 0.066 (2) | 0.066 (2) | 0.021 (2) | 0.009 (1) | 0.020 (1) |
C30* | 0.082 (2) | 0.059 (2) | 0.064 (2) | 0.005 (2) | 0.014 (2) | 0.007 (1) |
C31 | 0.085 (2) | 0.066 (2) | 0.087 (2) | 0.012 (2) | 0.011 (2) | 0.017 (2) |
C31* | 0.081 (2) | 0.069 (2) | 0.084 (2) | 0.004 (2) | 0.006 (2) | 0.007 (2) |
C32 | 0.114 (3) | 0.083 (2) | 0.103 (3) | 0.025 (2) | 0.010 (2) | 0.016 (2) |
C32* | 0.114 (3) | 0.084 (3) | 0.122 (3) | −0.001 (2) | 0.003 (3) | 0.030 (2) |
Geometric parameters (Å, º) top
O1—C10 | 1.272 (4) | C19*—C20* | 1.391 (7) |
O1—H1 | 0.64 (7) | C19*—H19* | 0.967 |
O1*—C10* | 1.281 (4) | C20—C21 | 1.385 (7) |
O1*—H1* | 0.86 (6) | C20—H20 | 0.961 |
O2—C10 | 1.249 (3) | C20*—C21* | 1.359 (7) |
O2—H2 | 0.74 (8) | C20*—H20* | 0.973 |
O2*—C10* | 1.247 (3) | C21—C22 | 1.410 (5) |
O2*—H2* | 1.01 (8) | C21—H21 | 0.965 |
O3—N7 | 1.199 (4) | C21*—C22* | 1.416 (6) |
O3*—N7* | 1.221 (3) | C21*—H21* | 0.966 |
O4—N7 | 1.211 (5) | C22—C23 | 1.433 (5) |
O4*—N7* | 1.214 (4) | C22*—C23* | 1.432 (5) |
O5—N8 | 1.211 (4) | C23—C24 | 1.380 (4) |
O5*—N8* | 1.207 (4) | C23—C28 | 1.410 (4) |
O6—N8 | 1.215 (4) | C23*—C24* | 1.398 (4) |
O6*—N8* | 1.211 (4) | C23*—C28* | 1.401 (4) |
N7—C13 | 1.477 (4) | C24—C25 | 1.361 (7) |
N7*—C13* | 1.463 (4) | C24—H24 | 0.976 |
N8—C15 | 1.475 (3) | C24*—C25* | 1.375 (7) |
N8*—C15* | 1.482 (3) | C24*—H24* | 0.978 |
N9—C17 | 1.384 (5) | C25—C26 | 1.374 (8) |
N9—C28 | 1.379 (4) | C25—H25 | 0.965 |
N9—C29 | 1.465 (4) | C25*—C26* | 1.390 (7) |
N9*—C17* | 1.383 (5) | C25*—H25* | 0.963 |
N9*—C28* | 1.386 (3) | C26—C27 | 1.379 (5) |
N9*—C29* | 1.448 (3) | C26—H26 | 0.971 |
C10—C11 | 1.487 (5) | C26*—C27* | 1.379 (4) |
C10*—C11* | 1.489 (4) | C26*—H26* | 0.970 |
C11—C12 | 1.385 (4) | C27—C28 | 1.400 (6) |
C11—C16 | 1.374 (3) | C27—H27 | 0.983 |
C11*—C12* | 1.390 (4) | C27*—C28* | 1.399 (5) |
C11*—C16* | 1.391 (3) | C27*—H27* | 0.977 |
C12—C13 | 1.369 (4) | C29—C30 | 1.495 (4) |
C12—H12 | 0.969 | C29—H29A | 0.972 |
C12*—C13* | 1.384 (4) | C29—H29B | 0.966 |
C12*—H12* | 0.973 | C29*—C30* | 1.504 (4) |
C13—C14 | 1.379 (3) | C29*—H29*A | 0.960 |
C13*—C14* | 1.377 (3) | C29*—H29*B | 0.964 |
C14—C15 | 1.370 (4) | C30—C31 | 1.529 (4) |
C14—H14 | 0.974 | C30—H30A | 0.955 |
C14*—C15* | 1.369 (4) | C30—H30B | 0.967 |
C14*—H14* | 0.971 | C30*—C31* | 1.512 (4) |
C15—C16 | 1.384 (4) | C30*—H30*A | 0.960 |
C15*—C16* | 1.379 (4) | C30*—H30*B | 0.985 |
C16—H16 | 0.981 | C31—C32 | 1.471 (4) |
C16*—H16* | 0.981 | C31—H31A | 0.966 |
C17—C18 | 1.403 (5) | C31—H31B | 0.967 |
C17—C22 | 1.394 (4) | C31*—C32* | 1.472 (5) |
C17*—C18* | 1.414 (4) | C31*—H31*A | 0.976 |
C17*—C22* | 1.406 (4) | C31*—H31*B | 0.974 |
C18—C19 | 1.361 (7) | C32—H32A | 0.960 |
C18—H18 | 0.984 | C32—H32B | 0.963 |
C18*—C19* | 1.386 (8) | C32—H32C | 0.962 |
C18*—H18* | 0.980 | C32*—H32*B | 0.975 |
C19—C20 | 1.386 (6) | C32*—H32*C | 0.971 |
C19—H19 | 0.981 | C32*—H32*A | 0.958 |
| | | |
C10—O1—H1 | 121 (4) | C20*—C21*—H21* | 120.3 |
C10*—O1*—H1* | 118 (3) | C22*—C21*—H21* | 120.7 |
C10—O2—H2 | 121 (4) | C17—C22—C21 | 118.8 (3) |
C10*—O2*—H2* | 114 (3) | C17—C22—C23 | 106.8 (3) |
O3—N7—O4 | 123.9 (3) | C21—C22—C23 | 134.4 (3) |
O3—N7—C13 | 118.7 (3) | C17*—C22*—C21* | 118.5 (3) |
O4—N7—C13 | 117.4 (2) | C17*—C22*—C23* | 106.7 (3) |
O3*—N7*—O4* | 124.3 (3) | C21*—C22*—C23* | 134.8 (2) |
O3*—N7*—C13* | 118.4 (3) | C22—C23—C24 | 134.8 (3) |
O4*—N7*—C13* | 117.3 (2) | C22—C23—C28 | 107.3 (2) |
O5—N8—O6 | 124.0 (2) | C24—C23—C28 | 117.9 (3) |
O5—N8—C15 | 118.5 (3) | C22*—C23*—C24* | 132.9 (3) |
O6—N8—C15 | 117.5 (3) | C22*—C23*—C28* | 106.9 (2) |
O5*—N8*—O6* | 124.1 (2) | C24*—C23*—C28* | 120.1 (3) |
O5*—N8*—C15* | 118.5 (3) | C23—C24—C25 | 120.1 (3) |
O6*—N8*—C15* | 117.5 (3) | C23—C24—H24 | 121.2 |
C17—N9—C28 | 109.4 (2) | C25—C24—H24 | 118.7 |
C17—N9—C29 | 124.4 (2) | C23*—C24*—C25* | 117.4 (3) |
C28—N9—C29 | 125.6 (3) | C23*—C24*—H24* | 120.4 |
C17*—N9*—C28* | 108.3 (2) | C25*—C24*—H24* | 122.1 |
C17*—N9*—C29* | 126.0 (2) | C24—C25—C26 | 121.4 (3) |
C28*—N9*—C29* | 125.6 (3) | C24—C25—H25 | 119.8 |
O1—C10—O2 | 125.2 (3) | C26—C25—H25 | 118.7 |
O1—C10—C11 | 116.3 (2) | C24*—C25*—C26* | 121.9 (3) |
O2—C10—C11 | 118.5 (3) | C24*—C25*—H25* | 118.9 |
O1*—C10*—O2* | 125.5 (3) | C26*—C25*—H25* | 119.2 |
O1*—C10*—C11* | 115.7 (2) | C25—C26—C27 | 121.7 (5) |
O2*—C10*—C11* | 118.8 (3) | C25—C26—H26 | 120.3 |
C10—C11—C12 | 119.3 (2) | C27—C26—H26 | 118.0 |
C10—C11—C16 | 120.8 (3) | C25*—C26*—C27* | 122.2 (4) |
C12—C11—C16 | 119.9 (3) | C25*—C26*—H26* | 118.8 |
C10*—C11*—C12* | 119.4 (2) | C27*—C26*—H26* | 119.1 |
C10*—C11*—C16* | 120.4 (2) | C26—C27—C28 | 116.4 (4) |
C12*—C11*—C16* | 120.2 (3) | C26—C27—H27 | 122.9 |
C11—C12—C13 | 118.9 (2) | C28—C27—H27 | 120.8 |
C11—C12—H12 | 120.9 | C26*—C27*—C28* | 116.0 (3) |
C13—C12—H12 | 120.2 | C26*—C27*—H27* | 122.1 |
C11*—C12*—C13* | 118.6 (2) | C28*—C27*—H27* | 121.9 |
C11*—C12*—H12* | 121.1 | N9—C28—C23 | 107.7 (3) |
C13*—C12*—H12* | 120.2 | N9—C28—C27 | 129.8 (3) |
N7—C13—C12 | 118.8 (2) | C23—C28—C27 | 122.5 (3) |
N7—C13—C14 | 117.9 (3) | N9*—C28*—C23* | 109.0 (3) |
C12—C13—C14 | 123.3 (3) | N9*—C28*—C27* | 128.6 (2) |
N7*—C13*—C12* | 118.5 (2) | C23*—C28*—C27* | 122.4 (2) |
N7*—C13*—C14* | 118.8 (3) | N9—C29—C30 | 115.5 (3) |
C12*—C13*—C14* | 122.8 (3) | N9—C29—H29A | 108.5 |
C13—C14—C15 | 116.0 (3) | N9—C29—H29B | 108.4 |
C13—C14—H14 | 122.2 | C30—C29—H29A | 107.7 |
C15—C14—H14 | 121.8 | C30—C29—H29B | 108.5 |
C13*—C14*—C15* | 116.6 (3) | H29A—C29—H29B | 107.9 |
C13*—C14*—H14* | 120.6 | N9*—C29*—C30* | 114.4 (3) |
C15*—C14*—H14* | 122.8 | N9*—C29*—H29*A | 107.9 |
N8—C15—C14 | 117.8 (3) | N9*—C29*—H29*B | 107.5 |
N8—C15—C16 | 119.1 (3) | C30*—C29*—H29*A | 108.5 |
C14—C15—C16 | 123.1 (2) | C30*—C29*—H29*B | 109.4 |
N8*—C15*—C14* | 118.2 (3) | H29*A—C29*—H29*B | 109.1 |
N8*—C15*—C16* | 118.1 (3) | C29—C30—C31 | 109.8 (2) |
C14*—C15*—C16* | 123.7 (2) | C29—C30—H30A | 110.6 |
C11—C16—C15 | 118.8 (2) | C29—C30—H30B | 109.7 |
C11—C16—H16 | 121.5 | C31—C30—H30A | 109.0 |
C15—C16—H16 | 119.7 | C31—C30—H30B | 108.3 |
C11*—C16*—C15* | 118.1 (2) | H30A—C30—H30B | 109.3 |
C11*—C16*—H16* | 120.7 | C29*—C30*—C31* | 113.2 (3) |
C15*—C16*—H16* | 121.2 | C29*—C30*—H30*A | 110.4 |
N9—C17—C18 | 129.5 (3) | C29*—C30*—H30*B | 109.0 |
N9—C17—C22 | 108.7 (3) | C31*—C30*—H30*A | 109.1 |
C18—C17—C22 | 121.8 (3) | C31*—C30*—H30*B | 107.6 |
N9*—C17*—C18* | 128.2 (3) | H30*A—C30*—H30*B | 107.4 |
N9*—C17*—C22* | 109.0 (3) | C30—C31—C32 | 113.9 (3) |
C18*—C17*—C22* | 122.8 (3) | C30—C31—H31A | 108.2 |
C17—C18—C19 | 118.9 (3) | C30—C31—H31B | 108.5 |
C17—C18—H18 | 119.3 | C32—C31—H31A | 108.9 |
C19—C18—H18 | 121.9 | C32—C31—H31B | 108.9 |
C17*—C18*—C19* | 115.6 (3) | H31A—C31—H31B | 108.4 |
C17*—C18*—H18* | 122.2 | C30*—C31*—C32* | 114.6 (3) |
C19*—C18*—H18* | 122.2 | C30*—C31*—H31*A | 107.6 |
C18—C19—C20 | 120.1 (4) | C30*—C31*—H31*B | 108.9 |
C18—C19—H19 | 120.0 | C32*—C31*—H31*A | 109.0 |
C20—C19—H19 | 119.9 | C32*—C31*—H31*B | 109.3 |
C18*—C19*—C20* | 122.5 (5) | H31*A—C31*—H31*B | 107.1 |
C18*—C19*—H19* | 120.3 | C31—C32—H32A | 110.1 |
C20*—C19*—H19* | 117.1 | C31—C32—H32B | 109.5 |
C19—C20—C21 | 122.5 (5) | C31—C32—H32C | 109.5 |
C19—C20—H20 | 117.7 | H32A—C32—H32B | 109.2 |
C21—C20—H20 | 119.8 | H32A—C32—H32C | 109.3 |
C19*—C20*—C21* | 121.5 (6) | H32B—C32—H32C | 109.1 |
C19*—C20*—H20* | 117.5 | C31*—C32*—H32*B | 109.9 |
C21*—C20*—H20* | 120.9 | C31*—C32*—H32*C | 110.3 |
C20—C21—C22 | 118.0 (3) | C31*—C32*—H32*A | 112.1 |
C20—C21—H21 | 120.4 | H32*B—C32*—H32*C | 107.3 |
C22—C21—H21 | 121.5 | H32*B—C32*—H32*A | 108.3 |
C20*—C21*—C22* | 119.0 (3) | H32*C—C32*—H32*A | 108.7 |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1···O2* | 0.64 (7) | 2.02 (7) | 2.651 (4) | 171 (6) |
O1*—H1*···O2 | 0.86 (6) | 1.82 (6) | 2.637 (4) | 158 (5) |
O2—H2···O1* | 0.74 (8) | 1.90 (8) | 2.637 (4) | 169 (8) |
O2*—H2*···O1 | 1.01 (8) | 1.65 (8) | 2.651 (4) | 170 (6) |
Crystal data top
C16H17N·C7H4N2O6 | Dx = 1.364 Mg m−3 |
Mr = 435.44 | Mo Kα radiation, λ = 0.71073 Å |
Monoclinic, P21/c | Cell parameters from 25 reflections |
a = 8.212 (2) Å | θ = 12.3–14.7° |
b = 31.924 (2) Å | µ = 0.10 mm−1 |
c = 8.438 (1) Å | T = 298 K |
β = 106.54 (1)° | Prism, orange |
V = 2120.5 (6) Å3 | 0.5 × 0.4 × 0.3 mm |
Z = 4 | |
Data collection top
Rigaku AFC-7R diffractometer | θmax = 27.5°, θmin = 2.5° |
ω scans | h = −11→11 |
5184 measured reflections | k = 0→41 |
4864 independent reflections | l = −11→0 |
2811 reflections with I > 2σ(I) | 3 standard reflections every 150 reflections |
Rint = 0.006 | intensity decay: none |
Refinement top
Refinement on F2 | w = 1/[σ2(Fo2) + (0.0409P)2 + 1.8479P] where P = (Fo2 + 2Fc2)/3 |
R[F2 > 2σ(F2)] = 0.049 | (Δ/σ)max = 0.001 |
wR(F2) = 0.165 | Δρmax = 0.20 e Å−3 |
S = 1.03 | Δρmin = −0.25 e Å−3 |
4864 reflections | Extinction correction: SHELXL97 (Sheldrick, 1997), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
298 parameters | Extinction coefficient: 0.0044 (7) |
H atoms treated by a mixture of independent and constrained refinement | |
Crystal data top
C16H17N·C7H4N2O6 | V = 2120.5 (6) Å3 |
Mr = 435.44 | Z = 4 |
Monoclinic, P21/c | Mo Kα radiation |
a = 8.212 (2) Å | µ = 0.10 mm−1 |
b = 31.924 (2) Å | T = 298 K |
c = 8.438 (1) Å | 0.5 × 0.4 × 0.3 mm |
β = 106.54 (1)° | |
Data collection top
Rigaku AFC-7R diffractometer | Rint = 0.006 |
5184 measured reflections | 3 standard reflections every 150 reflections |
4864 independent reflections | intensity decay: none |
2811 reflections with I > 2σ(I) | |
Refinement top
R[F2 > 2σ(F2)] = 0.049 | 298 parameters |
wR(F2) = 0.165 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.03 | Δρmax = 0.20 e Å−3 |
4864 reflections | Δρmin = −0.25 e Å−3 |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | Occ. (<1) |
O1 | 0.6288 (3) | 0.45743 (7) | −0.0189 (3) | 0.0671 (6) | |
O2 | 0.6442 (3) | 0.50128 (7) | 0.1912 (3) | 0.0699 (6) | |
O3 | 0.9712 (4) | 0.4595 (1) | 0.7416 (3) | 0.1084 (10) | |
O4 | 1.1433 (5) | 0.40767 (9) | 0.7761 (3) | 0.126 (1) | |
O5 | 1.1618 (3) | 0.32148 (7) | 0.3129 (3) | 0.0873 (7) | |
O6 | 0.9912 (3) | 0.33483 (8) | 0.0721 (3) | 0.0851 (7) | |
N7 | 1.0354 (4) | 0.43026 (9) | 0.6898 (3) | 0.0793 (8) | |
N8 | 1.0544 (3) | 0.34276 (7) | 0.2182 (4) | 0.0639 (6) | |
N9 | 0.5426 (3) | 0.34977 (7) | 0.2175 (3) | 0.0560 (6) | |
C10 | 0.6893 (4) | 0.46903 (8) | 0.1302 (3) | 0.0538 (6) | |
C11 | 0.8202 (3) | 0.44159 (8) | 0.2400 (3) | 0.0509 (6) | |
C12 | 0.8718 (4) | 0.44946 (8) | 0.4092 (3) | 0.0557 (7) | |
C13 | 0.9849 (4) | 0.42230 (9) | 0.5103 (3) | 0.0565 (7) | |
C14 | 1.0490 (3) | 0.38745 (8) | 0.4520 (3) | 0.0581 (7) | |
C15 | 0.9941 (3) | 0.38056 (8) | 0.2846 (3) | 0.0532 (6) | |
C16 | 0.8814 (3) | 0.40684 (8) | 0.1767 (3) | 0.0532 (6) | |
C17 | 0.6518 (4) | 0.33008 (9) | 0.3521 (3) | 0.0581 (7) | |
C18 | 0.7513 (4) | 0.2947 (1) | 0.3567 (4) | 0.0702 (8) | |
C19 | 0.8561 (4) | 0.2825 (1) | 0.5092 (5) | 0.085 (1) | |
C20 | 0.8614 (4) | 0.3042 (1) | 0.6531 (4) | 0.089 (1) | |
C21 | 0.7607 (4) | 0.3388 (1) | 0.6492 (4) | 0.079 (1) | |
C22 | 0.6543 (4) | 0.3521 (1) | 0.4974 (3) | 0.0615 (7) | |
C23 | 0.5408 (4) | 0.3871 (1) | 0.4471 (3) | 0.0617 (7) | |
C24 | 0.4940 (5) | 0.4209 (1) | 0.5301 (4) | 0.0768 (10) | |
C25 | 0.3856 (5) | 0.4505 (1) | 0.4420 (5) | 0.085 (1) | |
C26 | 0.3198 (4) | 0.44778 (9) | 0.2709 (5) | 0.0788 (10) | |
C27 | 0.3625 (4) | 0.41464 (9) | 0.1836 (3) | 0.0649 (8) | |
C28 | 0.4746 (4) | 0.38472 (9) | 0.2734 (3) | 0.0564 (7) | |
C29 | 0.5275 (3) | 0.34156 (7) | 0.0433 (3) | 0.0547 (7) | |
C30 | 0.3687 (3) | 0.31808 (8) | −0.0511 (3) | 0.0499 (6) | |
C31 | 0.3676 (3) | 0.31583 (8) | −0.2309 (3) | 0.0665 (8) | |
C32 | 0.3584 (4) | 0.27506 (9) | 0.0194 (3) | 0.0721 (9) | |
H1 | 0.559 (9) | 0.473 (2) | −0.076 (8) | 0.0595 (2)* | 0.50 |
H2 | 0.56 (1) | 0.517 (3) | 0.130 (10) | 0.1044 (4)* | 0.50 |
H12 | 0.8323 | 0.4738 | 0.4548 | 0.0629* | |
H14 | 1.1304 | 0.3693 | 0.5249 | 0.0655* | |
H16 | 0.8478 | 0.4010 | 0.0597 | 0.0603* | |
H18 | 0.7487 | 0.2789 | 0.2594 | 0.0808* | |
H19 | 0.9276 | 0.2584 | 0.5178 | 0.0974* | |
H20 | 0.9390 | 0.2956 | 0.7581 | 0.0988* | |
H21 | 0.7596 | 0.3535 | 0.7498 | 0.0882* | |
H24 | 0.5361 | 0.4231 | 0.6480 | 0.0898* | |
H25 | 0.3536 | 0.4738 | 0.4982 | 0.0940* | |
H26 | 0.2410 | 0.4692 | 0.2111 | 0.0941* | |
H27 | 0.3170 | 0.4127 | 0.0647 | 0.0711* | |
H29A | 0.5303 | 0.3680 | −0.0124 | 0.0618* | |
H29B | 0.6246 | 0.3252 | 0.0373 | 0.0618* | |
H30 | 0.2716 | 0.3343 | −0.0452 | 0.0549* | |
H31A | 0.3679 | 0.3434 | −0.2763 | 0.0742* | |
H31B | 0.4659 | 0.3007 | −0.2407 | 0.0742* | |
H31C | 0.2668 | 0.3012 | −0.2947 | 0.0742* | |
H32A | 0.3607 | 0.2772 | 0.1339 | 0.0832* | |
H32B | 0.4529 | 0.2581 | 0.0114 | 0.0832* | |
H32C | 0.2542 | 0.2614 | −0.0408 | 0.0832* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O1 | 0.073 (1) | 0.070 (1) | 0.052 (1) | 0.016 (1) | 0.007 (1) | 0.003 (1) |
O2 | 0.074 (1) | 0.059 (1) | 0.069 (1) | 0.015 (1) | 0.007 (1) | −0.004 (1) |
O3 | 0.127 (2) | 0.123 (2) | 0.066 (2) | 0.028 (2) | 0.011 (1) | −0.024 (2) |
O4 | 0.186 (3) | 0.092 (2) | 0.064 (2) | 0.042 (2) | −0.022 (2) | 0.003 (1) |
O5 | 0.093 (2) | 0.070 (1) | 0.095 (2) | 0.031 (1) | 0.022 (1) | 0.012 (1) |
O6 | 0.088 (2) | 0.089 (2) | 0.075 (2) | 0.017 (1) | 0.016 (1) | −0.021 (1) |
N7 | 0.102 (2) | 0.068 (2) | 0.057 (2) | 0.002 (2) | 0.004 (2) | −0.002 (1) |
N8 | 0.062 (2) | 0.055 (1) | 0.077 (2) | 0.005 (1) | 0.024 (1) | 0.001 (1) |
N9 | 0.066 (1) | 0.057 (1) | 0.044 (1) | −0.007 (1) | 0.015 (1) | −0.008 (1) |
C10 | 0.058 (2) | 0.049 (1) | 0.052 (2) | 0.001 (1) | 0.013 (1) | 0.001 (1) |
C11 | 0.050 (1) | 0.047 (1) | 0.054 (2) | −0.004 (1) | 0.012 (1) | 0.003 (1) |
C12 | 0.061 (2) | 0.047 (1) | 0.058 (2) | −0.003 (1) | 0.014 (1) | −0.003 (1) |
C13 | 0.064 (2) | 0.053 (2) | 0.047 (1) | −0.006 (1) | 0.008 (1) | 0.002 (1) |
C14 | 0.062 (2) | 0.047 (1) | 0.060 (2) | −0.002 (1) | 0.008 (1) | 0.008 (1) |
C15 | 0.054 (2) | 0.046 (1) | 0.059 (2) | −0.004 (1) | 0.015 (1) | 0.001 (1) |
C16 | 0.054 (2) | 0.051 (1) | 0.053 (1) | −0.004 (1) | 0.013 (1) | 0.002 (1) |
C17 | 0.057 (2) | 0.065 (2) | 0.054 (2) | −0.013 (1) | 0.018 (1) | −0.003 (1) |
C18 | 0.068 (2) | 0.077 (2) | 0.066 (2) | −0.004 (2) | 0.020 (2) | 0.001 (2) |
C19 | 0.069 (2) | 0.097 (3) | 0.089 (3) | 0.007 (2) | 0.024 (2) | 0.016 (2) |
C20 | 0.069 (2) | 0.128 (3) | 0.065 (2) | −0.007 (2) | 0.012 (2) | 0.018 (2) |
C21 | 0.070 (2) | 0.115 (3) | 0.052 (2) | −0.020 (2) | 0.019 (2) | −0.002 (2) |
C22 | 0.059 (2) | 0.080 (2) | 0.047 (2) | −0.020 (2) | 0.018 (1) | −0.008 (1) |
C23 | 0.068 (2) | 0.069 (2) | 0.054 (2) | −0.025 (2) | 0.025 (1) | −0.016 (1) |
C24 | 0.087 (2) | 0.084 (2) | 0.069 (2) | −0.028 (2) | 0.037 (2) | −0.031 (2) |
C25 | 0.102 (3) | 0.068 (2) | 0.100 (3) | −0.021 (2) | 0.052 (2) | −0.032 (2) |
C26 | 0.087 (2) | 0.056 (2) | 0.103 (3) | −0.011 (2) | 0.042 (2) | −0.011 (2) |
C27 | 0.075 (2) | 0.054 (2) | 0.068 (2) | −0.014 (1) | 0.024 (2) | −0.004 (1) |
C28 | 0.068 (2) | 0.052 (2) | 0.053 (2) | −0.017 (1) | 0.023 (1) | −0.012 (1) |
C29 | 0.064 (2) | 0.056 (2) | 0.047 (1) | −0.010 (1) | 0.021 (1) | −0.009 (1) |
C30 | 0.054 (1) | 0.045 (1) | 0.052 (1) | −0.001 (1) | 0.016 (1) | −0.008 (1) |
C31 | 0.075 (2) | 0.069 (2) | 0.054 (2) | −0.003 (2) | 0.014 (1) | −0.014 (1) |
C32 | 0.085 (2) | 0.053 (2) | 0.077 (2) | −0.015 (2) | 0.020 (2) | −0.004 (1) |
Geometric parameters (Å, º) top
O1—C10 | 1.269 (3) | C19—H19 | 0.959 |
O1—H1 | 0.80 (6) | C20—C21 | 1.374 (6) |
O2—C10 | 1.253 (4) | C20—H20 | 0.972 |
O2—H2 | 0.90 (8) | C21—C22 | 1.396 (4) |
O3—N7 | 1.212 (4) | C21—H21 | 0.972 |
O4—N7 | 1.212 (4) | C22—C23 | 1.437 (4) |
O5—N8 | 1.215 (3) | C23—C24 | 1.398 (5) |
O6—N8 | 1.220 (4) | C23—C28 | 1.413 (4) |
N7—C13 | 1.473 (4) | C24—C25 | 1.364 (5) |
N8—C15 | 1.474 (4) | C24—H24 | 0.958 |
N9—C17 | 1.382 (3) | C25—C26 | 1.392 (5) |
N9—C28 | 1.389 (4) | C25—H25 | 0.960 |
N9—C29 | 1.464 (4) | C26—C27 | 1.390 (5) |
C10—C11 | 1.488 (3) | C26—H26 | 0.978 |
C11—C12 | 1.391 (4) | C27—C28 | 1.391 (4) |
C11—C16 | 1.386 (4) | C27—H27 | 0.968 |
C12—C13 | 1.375 (4) | C29—C30 | 1.519 (3) |
C12—H12 | 0.965 | C29—H29A | 0.969 |
C13—C14 | 1.380 (4) | C29—H29B | 0.966 |
C14—C15 | 1.373 (4) | C30—C31 | 1.516 (4) |
C14—H14 | 0.963 | C30—C32 | 1.509 (4) |
C15—C16 | 1.382 (3) | C30—H30 | 0.963 |
C16—H16 | 0.965 | C31—H31A | 0.961 |
C17—C18 | 1.388 (4) | C31—H31B | 0.964 |
C17—C22 | 1.409 (4) | C31—H31C | 0.969 |
C18—C19 | 1.385 (4) | C32—H32A | 0.963 |
C18—H18 | 0.959 | C32—H32B | 0.964 |
C19—C20 | 1.388 (6) | C32—H32C | 0.966 |
| | | |
C10—O1—H1 | 116 (5) | C22—C21—H21 | 119.7 |
C10—O2—H2 | 120 (5) | C17—C22—C21 | 119.8 (3) |
O3—N7—O4 | 124.0 (3) | C17—C22—C23 | 106.5 (2) |
O3—N7—C13 | 118.7 (3) | C21—C22—C23 | 133.7 (3) |
O4—N7—C13 | 117.3 (3) | C22—C23—C24 | 134.3 (3) |
O5—N8—O6 | 124.7 (3) | C22—C23—C28 | 106.9 (3) |
O5—N8—C15 | 117.9 (3) | C24—C23—C28 | 118.7 (3) |
O6—N8—C15 | 117.5 (2) | C23—C24—C25 | 119.4 (3) |
C17—N9—C28 | 108.4 (2) | C23—C24—H24 | 120.5 |
C17—N9—C29 | 126.4 (2) | C25—C24—H24 | 120.0 |
C28—N9—C29 | 123.9 (2) | C24—C25—C26 | 121.5 (3) |
O1—C10—O2 | 124.7 (2) | C24—C25—H25 | 119.8 |
O1—C10—C11 | 117.0 (2) | C26—C25—H25 | 118.7 |
O2—C10—C11 | 118.3 (2) | C25—C26—C27 | 120.9 (3) |
C10—C11—C12 | 119.2 (2) | C25—C26—H26 | 119.8 |
C10—C11—C16 | 120.5 (2) | C27—C26—H26 | 119.3 |
C12—C11—C16 | 120.1 (2) | C26—C27—C28 | 117.5 (3) |
C11—C12—C13 | 118.5 (3) | C26—C27—H27 | 121.2 |
C11—C12—H12 | 121.1 | C28—C27—H27 | 121.3 |
C13—C12—H12 | 120.4 | N9—C28—C23 | 108.7 (2) |
N7—C13—C12 | 118.1 (3) | N9—C28—C27 | 129.4 (2) |
N7—C13—C14 | 118.8 (2) | C23—C28—C27 | 121.9 (3) |
C12—C13—C14 | 123.1 (2) | N9—C29—C30 | 115.4 (2) |
C13—C14—C15 | 116.7 (2) | N9—C29—H29A | 108.9 |
C13—C14—H14 | 121.6 | N9—C29—H29B | 108.3 |
C15—C14—H14 | 121.7 | C30—C29—H29A | 108.1 |
N8—C15—C14 | 118.3 (2) | C30—C29—H29B | 107.7 |
N8—C15—C16 | 118.8 (2) | H29A—C29—H29B | 108.2 |
C14—C15—C16 | 122.9 (3) | C29—C30—C31 | 107.9 (2) |
C11—C16—C15 | 118.7 (2) | C29—C30—C32 | 112.2 (2) |
C11—C16—H16 | 121.4 | C29—C30—H30 | 107.9 |
C15—C16—H16 | 119.9 | C31—C30—C32 | 111.5 (2) |
N9—C17—C18 | 129.2 (3) | C31—C30—H30 | 107.9 |
N9—C17—C22 | 109.4 (2) | C32—C30—H30 | 109.1 |
C18—C17—C22 | 121.3 (2) | C30—C31—H31A | 110.8 |
C17—C18—C19 | 117.4 (3) | C30—C31—H31B | 110.1 |
C17—C18—H18 | 122.4 | C30—C31—H31C | 109.8 |
C19—C18—H18 | 120.2 | H31A—C31—H31B | 109.1 |
C18—C19—C20 | 121.8 (3) | H31A—C31—H31C | 108.6 |
C18—C19—H19 | 120.1 | H31B—C31—H31C | 108.4 |
C20—C19—H19 | 118.0 | C30—C32—H32A | 110.2 |
C19—C20—C21 | 120.8 (3) | C30—C32—H32B | 110.2 |
C19—C20—H20 | 120.3 | C30—C32—H32C | 110.2 |
C21—C20—H20 | 118.9 | H32A—C32—H32B | 108.9 |
C20—C21—C22 | 118.8 (3) | H32A—C32—H32C | 108.7 |
C20—C21—H21 | 121.5 | H32B—C32—H32C | 108.6 |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1···O2i | 0.80 (6) | 1.87 (7) | 2.650 (3) | 165 (8) |
O2—H2···O1i | 0.90 (8) | 1.76 (8) | 2.650 (3) | 171 (9) |
Symmetry code: (i) −x+1, −y+1, −z. |
Experimental details
| (I) | (II) | (III) | (IV) |
Crystal data |
Chemical formula | C13H11N·C7H4N2O6 | C15H15N·C7H4N2O6 | C16H17N·C7H4N2O6 | C16H17N·C7H4N2O6 |
Mr | 393.36 | 421.41 | 435.44 | 435.44 |
Crystal system, space group | Triclinic, P1 | Monoclinic, P21/a | Triclinic, P1 | Monoclinic, P21/c |
Temperature (K) | 298 | 298 | 298 | 298 |
a, b, c (Å) | 8.414 (1), 15.763 (2), 6.991 (1) | 8.504 (2), 29.533 (4), 8.568 (2) | 16.723 (2), 16.784 (3), 8.4129 (9) | 8.212 (2), 31.924 (2), 8.438 (1) |
α, β, γ (°) | 91.82 (1), 99.91 (1), 81.59 (1) | 90, 108.05 (2), 90 | 102.36 (1), 92.34 (1), 109.91 (1) | 90, 106.54 (1), 90 |
V (Å3) | 903.6 (2) | 2045.8 (7) | 2152.0 (6) | 2120.5 (6) |
Z | 2 | 4 | 4 | 4 |
Radiation type | Mo Kα | Mo Kα | Mo Kα | Mo Kα |
µ (mm−1) | 0.11 | 0.10 | 0.10 | 0.10 |
Crystal size (mm) | 0.6 × 0.4 × 0.1 | 0.5 × 0.5 × 0.5 | 0.6 × 0.5 × 0.2 | 0.5 × 0.4 × 0.3 |
|
Data collection |
Diffractometer | Rigaku AFC-7R diffractometer | Rigaku AFC-7R diffractometer | Rigaku AFC-7R diffractometer | Rigaku AFC-7R diffractometer |
Absorption correction | – | – | – | – |
No. of measured, independent and observed [I > 2σ(I)] reflections | 5045, 4128, 2977 | 4990, 4685, 3283 | 10208, 9870, 4817 | 5184, 4864, 2811 |
Rint | 0.005 | 0.011 | 0.010 | 0.006 |
(sin θ/λ)max (Å−1) | 0.650 | 0.650 | 0.650 | 0.650 |
|
Refinement |
R[F2 > 2σ(F2)], wR(F2), S | 0.044, 0.147, 1.08 | 0.041, 0.122, 1.05 | 0.061, 0.192, 1.74 | 0.049, 0.165, 1.03 |
No. of reflections | 4128 | 4685 | 9870 | 4864 |
No. of parameters | 270 | 288 | 593 | 298 |
No. of restraints | ? | ? | ? | ? |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement | H atoms treated by a mixture of independent and constrained refinement | H atoms treated by a mixture of independent and constrained refinement | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.29, −0.18 | 0.21, −0.16 | 0.24, −0.25 | 0.20, −0.25 |
Selected geometric parameters (Å, º) for (I) topO1—C10 | 1.260 (2) | O5—N8 | 1.214 (2) |
O2—C10 | 1.265 (2) | O6—N8 | 1.222 (2) |
O3—N7 | 1.213 (2) | N9—C29 | 1.449 (2) |
O4—N7 | 1.220 (2) | | |
| | | |
O3—N7—O4 | 124.5 (2) | O1—C10—C11 | 117.8 (1) |
O5—N8—O6 | 123.8 (2) | O2—C10—C11 | 117.7 (2) |
O1—C10—O2 | 124.4 (1) | | |
Hydrogen-bond geometry (Å, º) for (I) top
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1···O2i | 0.73 (5) | 1.92 (5) | 2.648 (2) | 172 (5) |
O2—H2···O1i | 0.88 (5) | 1.77 (5) | 2.648 (2) | 179 (5) |
Symmetry code: (i) −x+1, −y+1, −z+1. |
Selected geometric parameters (Å, º) for (II) topO1—C10 | 1.251 (2) | O6—N8 | 1.215 (2) |
O2—C10 | 1.266 (2) | N9—C29 | 1.474 (2) |
O3—N7 | 1.216 (3) | C29—C30 | 1.518 (3) |
O4—N7 | 1.214 (2) | C29—C31 | 1.521 (3) |
O5—N8 | 1.215 (2) | | |
| | | |
O3—N7—O4 | 124.1 (2) | O1—C10—C11 | 118.1 (1) |
O5—N8—O6 | 124.8 (2) | O2—C10—C11 | 117.1 (1) |
O1—C10—O2 | 124.8 (1) | | |
Hydrogen-bond geometry (Å, º) for (II) top
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1···O2i | 0.78 (4) | 1.86 (4) | 2.629 (2) | 174 (5) |
O2—H2···O1i | 0.82 (4) | 1.81 (4) | 2.629 (2) | 178 (4) |
Symmetry code: (i) −x, −y, −z+2. |
Selected geometric parameters (Å, º) for (III) topO1—C10 | 1.272 (4) | O6—N8 | 1.215 (4) |
O1*—C10* | 1.281 (4) | O6*—N8* | 1.211 (4) |
O2—C10 | 1.249 (3) | N9—C29 | 1.465 (4) |
O2*—C10* | 1.247 (3) | N9*—C29* | 1.448 (3) |
O3—N7 | 1.199 (4) | C29—C30 | 1.495 (4) |
O3*—N7* | 1.221 (3) | C29*—C30* | 1.504 (4) |
O4—N7 | 1.211 (5) | C30—C31 | 1.529 (4) |
O4*—N7* | 1.214 (4) | C30*—C31* | 1.512 (4) |
O5—N8 | 1.211 (4) | C31—C32 | 1.471 (4) |
O5*—N8* | 1.207 (4) | C31*—C32* | 1.472 (5) |
| | | |
O3—N7—O4 | 123.9 (3) | O1—C10—C11 | 116.3 (2) |
O3*—N7*—O4* | 124.3 (3) | O2—C10—C11 | 118.5 (3) |
O5—N8—O6 | 124.0 (2) | O1*—C10*—O2* | 125.5 (3) |
O5*—N8*—O6* | 124.1 (2) | O1*—C10*—C11* | 115.7 (2) |
O1—C10—O2 | 125.2 (3) | O2*—C10*—C11* | 118.8 (3) |
Hydrogen-bond geometry (Å, º) for (III) top
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1···O2* | 0.64 (7) | 2.02 (7) | 2.651 (4) | 171 (6) |
O1*—H1*···O2 | 0.86 (6) | 1.82 (6) | 2.637 (4) | 158 (5) |
O2—H2···O1* | 0.74 (8) | 1.90 (8) | 2.637 (4) | 169 (8) |
O2*—H2*···O1 | 1.01 (8) | 1.65 (8) | 2.651 (4) | 170 (6) |
Selected geometric parameters (Å, º) for (IV) topO1—C10 | 1.269 (3) | O6—N8 | 1.220 (4) |
O2—C10 | 1.253 (4) | N9—C29 | 1.464 (4) |
O3—N7 | 1.212 (4) | C29—C30 | 1.519 (3) |
O4—N7 | 1.212 (4) | C30—C31 | 1.516 (4) |
O5—N8 | 1.215 (3) | C30—C32 | 1.509 (4) |
| | | |
O3—N7—O4 | 124.0 (3) | O1—C10—C11 | 117.0 (2) |
O5—N8—O6 | 124.7 (3) | O2—C10—C11 | 118.3 (2) |
O1—C10—O2 | 124.7 (2) | | |
Hydrogen-bond geometry (Å, º) for (IV) top
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1···O2i | 0.80 (6) | 1.87 (7) | 2.650 (3) | 165 (8) |
O2—H2···O1i | 0.90 (8) | 1.76 (8) | 2.650 (3) | 171 (9) |
Symmetry code: (i) −x+1, −y+1, −z. |
Crystals of (I) underwent photoredox reactions initiated by the excited nitro group, leading to α-oxidation of the N-alkyl groups. Complexes (III) and (IV) were less photoreactive than (I), and no reaction was observed for (II) (Ito et al., 1998).
In (I), the N-methyl group of the donor is nearly eclipsed to one of the nitro groups of the neighboring acceptor in a column, whereas the N-isopropyl, N-butyl and N-isobutyl groups are in anti positions with respect to one of the nitro groups of the neighboring acceptor in (II)-(IV).