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The interaction of the antimigraine pharmaceutical agent frovatriptan with acetic acid and succinic acid yields the salts (±)-6-carbamoyl-
N-methyl-2,3,4,9-tetrahydro-1
H-carbazol-3-aminium acetate, C
14H
18N
3O
+·C
2H
3O
2−, (I), (
R)-(+)-6-carbamoyl-
N-methyl-2,3,4,9-tetrahydro-1
H-carbazol-3-aminium 3-carboxypropanoate monohydrate, C
14H
18N
3O
+·C
4H
5O
4−·H
2O, (II), and bis[(
R)-(+)-6-carbamoyl-
N-methyl-2,3,4,9-tetrahydro-1
H-carbazol-3-aminium] succinate trihydrate, 2C
14H
18N
3O
+·C
4H
4O
42−·3H
2O, (III). The methylazaniumyl substitutent is oriented differently in all three structures. Additionally, the amide group in (I) is in a different orientation. All the salts form three-dimensional hydrogen-bonded structures. In (I), the cations form head-to-head hydrogen-bonded amide–amide catemers through N—H
O interactions, while in (II) and (III) the cations form head-to-head amide–amide dimers. The cation catemers in (I) are extended into a three-dimensional network through further interactions with acetate anion acceptors. The presence of succinate anions and water molecules in (II) and (III) primarily governs the three-dimensional network through water-bridged cation–anion associations
via O—H
O and N—H
O hydrogen bonds. The structures reported here shed some light on the possible mode of noncovalent interactions in the aggregation and interaction patterns of drug molecule adducts.
Supporting information
CCDC references: 934621; 934622; 934623
For all compounds, data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT (Bruker, 2001); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: DIAMOND (Brandenburg & Putz, 2005) and Mercury (Macrae et al., 2008); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).
(I) (±)-6-Carbamoyl-
N-methyl-2,3,4,9-tetrahydro-1
H-carbazol-3-aminium
acetate
top
Crystal data top
C14H18N3O+·C2H3O2− | F(000) = 648 |
Mr = 303.36 | Dx = 1.247 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 2571 reflections |
a = 11.2397 (8) Å | θ = 2.2–22.0° |
b = 16.7124 (13) Å | µ = 0.09 mm−1 |
c = 8.6528 (6) Å | T = 294 K |
β = 96.150 (1)° | Block, colorless |
V = 1616.0 (2) Å3 | 0.17 × 0.15 × 0.07 mm |
Z = 4 | |
Data collection top
CCD Area Detector diffractometer | 2160 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.045 |
Graphite monochromator | θmax = 25.0°, θmin = 1.8° |
ω scan | h = −13→13 |
15459 measured reflections | k = −19→19 |
2855 independent reflections | l = −10→10 |
Refinement top
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.050 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.120 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.06 | w = 1/[σ2(Fo2) + (0.0511P)2 + 0.4523P] where P = (Fo2 + 2Fc2)/3 |
2855 reflections | (Δ/σ)max < 0.001 |
221 parameters | Δρmax = 0.19 e Å−3 |
0 restraints | Δρmin = −0.13 e Å−3 |
Special details top
Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell e.s.d.'s are taken
into account individually in the estimation of e.s.d.'s in distances, angles
and torsion angles; correlations between e.s.d.'s in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s.
planes. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
C1 | 0.15669 (17) | 0.06969 (12) | 0.6091 (2) | 0.0368 (5) | |
C2 | 0.17256 (18) | 0.03688 (14) | 0.7713 (2) | 0.0449 (6) | |
H2A | 0.1031 | 0.0053 | 0.7900 | 0.054* | |
H2B | 0.1800 | 0.0806 | 0.8455 | 0.054* | |
C3 | 0.28480 (18) | −0.01529 (13) | 0.7927 (2) | 0.0416 (5) | |
H3 | 0.2656 | −0.0668 | 0.7420 | 0.050* | |
C4 | 0.39019 (19) | 0.02022 (14) | 0.7218 (2) | 0.0459 (6) | |
H4A | 0.4592 | −0.0144 | 0.7439 | 0.055* | |
H4B | 0.4097 | 0.0719 | 0.7689 | 0.055* | |
C5 | 0.36346 (18) | 0.03042 (14) | 0.5460 (2) | 0.0432 (5) | |
H5A | 0.4235 | 0.0645 | 0.5071 | 0.052* | |
H5B | 0.3655 | −0.0212 | 0.4951 | 0.052* | |
C6 | 0.24322 (17) | 0.06705 (12) | 0.5115 (2) | 0.0378 (5) | |
C7 | 0.09019 (18) | 0.13105 (13) | 0.3805 (2) | 0.0382 (5) | |
C8 | 0.01499 (19) | 0.17453 (14) | 0.2741 (2) | 0.0484 (6) | |
H8 | 0.0390 | 0.1896 | 0.1787 | 0.058* | |
C9 | −0.09617 (19) | 0.19463 (14) | 0.3142 (2) | 0.0445 (6) | |
H9 | −0.1473 | 0.2244 | 0.2449 | 0.053* | |
C10 | −0.13513 (17) | 0.17166 (12) | 0.4565 (2) | 0.0343 (5) | |
C11 | −0.05850 (17) | 0.12963 (12) | 0.5627 (2) | 0.0362 (5) | |
H11 | −0.0834 | 0.1147 | 0.6576 | 0.043* | |
C12 | 0.05580 (17) | 0.10965 (12) | 0.5279 (2) | 0.0351 (5) | |
C13 | −0.25671 (17) | 0.19209 (12) | 0.5001 (2) | 0.0337 (5) | |
C14 | 0.2281 (2) | −0.06681 (16) | 1.0492 (3) | 0.0580 (7) | |
H14A | 0.1655 | −0.0284 | 1.0571 | 0.087* | |
H14B | 0.2625 | −0.0817 | 1.1515 | 0.087* | |
H14C | 0.1956 | −0.1134 | 0.9951 | 0.087* | |
N1 | 0.20370 (15) | 0.10322 (11) | 0.3724 (2) | 0.0427 (5) | |
H1N | 0.2483 (19) | 0.1081 (12) | 0.293 (3) | 0.044 (6)* | |
N2 | 0.32219 (17) | −0.03103 (13) | 0.9622 (2) | 0.0425 (5) | |
H2N | 0.388 (2) | −0.0659 (14) | 0.972 (2) | 0.051 (6)* | |
H3N | 0.347 (2) | 0.0198 (17) | 1.016 (3) | 0.071 (8)* | |
N3 | −0.32981 (18) | 0.23459 (13) | 0.4017 (2) | 0.0500 (5) | |
H4N | −0.310 (2) | 0.2531 (14) | 0.316 (3) | 0.049 (7)* | |
H5N | −0.395 (2) | 0.2532 (15) | 0.437 (3) | 0.060 (7)* | |
O1 | −0.28853 (12) | 0.17014 (9) | 0.62550 (16) | 0.0453 (4) | |
C15 | 0.58316 (19) | −0.16208 (13) | 0.9070 (2) | 0.0398 (5) | |
C16 | 0.6166 (3) | −0.24560 (16) | 0.8658 (4) | 0.0777 (9) | |
H16A | 0.6839 | −0.2630 | 0.9354 | 0.116* | |
H16B | 0.6373 | −0.2466 | 0.7610 | 0.116* | |
H16C | 0.5501 | −0.2807 | 0.8746 | 0.116* | |
O2 | 0.49328 (13) | −0.15188 (9) | 0.97702 (18) | 0.0503 (4) | |
O3 | 0.64897 (14) | −0.10589 (9) | 0.87036 (18) | 0.0526 (4) | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
C1 | 0.0336 (11) | 0.0425 (12) | 0.0348 (11) | 0.0049 (9) | 0.0054 (9) | 0.0032 (9) |
C2 | 0.0377 (12) | 0.0576 (15) | 0.0405 (12) | 0.0085 (10) | 0.0084 (10) | 0.0086 (10) |
C3 | 0.0398 (12) | 0.0477 (13) | 0.0367 (12) | 0.0052 (10) | 0.0008 (9) | 0.0025 (10) |
C4 | 0.0353 (12) | 0.0541 (14) | 0.0483 (13) | 0.0096 (10) | 0.0044 (10) | 0.0025 (11) |
C5 | 0.0376 (12) | 0.0481 (13) | 0.0455 (13) | 0.0080 (10) | 0.0116 (10) | 0.0024 (10) |
C6 | 0.0343 (11) | 0.0425 (12) | 0.0371 (11) | 0.0033 (10) | 0.0061 (9) | 0.0016 (9) |
C7 | 0.0333 (11) | 0.0479 (13) | 0.0342 (11) | 0.0044 (9) | 0.0079 (9) | 0.0020 (9) |
C8 | 0.0438 (13) | 0.0685 (16) | 0.0347 (12) | 0.0065 (11) | 0.0123 (10) | 0.0135 (11) |
C9 | 0.0375 (12) | 0.0594 (15) | 0.0369 (11) | 0.0110 (11) | 0.0056 (9) | 0.0112 (10) |
C10 | 0.0322 (11) | 0.0385 (12) | 0.0324 (10) | 0.0012 (9) | 0.0033 (8) | −0.0015 (9) |
C11 | 0.0369 (11) | 0.0415 (12) | 0.0314 (11) | −0.0001 (9) | 0.0087 (9) | 0.0001 (9) |
C12 | 0.0319 (11) | 0.0401 (12) | 0.0337 (11) | 0.0025 (9) | 0.0053 (9) | 0.0003 (9) |
C13 | 0.0339 (11) | 0.0363 (11) | 0.0312 (11) | −0.0004 (9) | 0.0043 (9) | −0.0037 (9) |
C14 | 0.0617 (16) | 0.0637 (16) | 0.0498 (14) | 0.0020 (13) | 0.0107 (12) | 0.0176 (12) |
N1 | 0.0350 (10) | 0.0599 (12) | 0.0353 (10) | 0.0086 (8) | 0.0138 (8) | 0.0069 (9) |
N2 | 0.0413 (11) | 0.0449 (12) | 0.0409 (11) | 0.0098 (10) | 0.0021 (8) | 0.0059 (9) |
N3 | 0.0412 (12) | 0.0674 (14) | 0.0439 (12) | 0.0188 (10) | 0.0155 (10) | 0.0128 (10) |
O1 | 0.0392 (8) | 0.0606 (10) | 0.0376 (8) | 0.0057 (7) | 0.0114 (6) | 0.0049 (7) |
C15 | 0.0397 (12) | 0.0428 (13) | 0.0376 (11) | 0.0035 (10) | 0.0066 (10) | 0.0027 (10) |
C16 | 0.088 (2) | 0.0523 (16) | 0.097 (2) | 0.0116 (15) | 0.0285 (17) | −0.0032 (15) |
O2 | 0.0453 (9) | 0.0471 (9) | 0.0618 (10) | 0.0023 (7) | 0.0207 (8) | 0.0062 (8) |
O3 | 0.0549 (10) | 0.0512 (10) | 0.0560 (10) | −0.0063 (8) | 0.0254 (8) | −0.0019 (8) |
Geometric parameters (Å, º) top
C1—C6 | 1.355 (3) | C9—H9 | 0.9300 |
C1—C12 | 1.433 (3) | C10—C11 | 1.382 (3) |
C1—C2 | 1.499 (3) | C10—C13 | 1.496 (3) |
C2—C3 | 1.528 (3) | C11—C12 | 1.391 (3) |
C2—H2A | 0.9700 | C11—H11 | 0.9300 |
C2—H2B | 0.9700 | C13—O1 | 1.234 (2) |
C3—N2 | 1.505 (3) | C13—N3 | 1.325 (3) |
C3—C4 | 1.512 (3) | C14—N2 | 1.488 (3) |
C3—H3 | 0.9800 | C14—H14A | 0.9600 |
C4—C5 | 1.529 (3) | C14—H14B | 0.9600 |
C4—H4A | 0.9700 | C14—H14C | 0.9600 |
C4—H4B | 0.9700 | N1—H1N | 0.90 (2) |
C5—C6 | 1.484 (3) | N2—H2N | 0.94 (2) |
C5—H5A | 0.9700 | N2—H3N | 0.99 (3) |
C5—H5B | 0.9700 | N3—H4N | 0.86 (2) |
C6—N1 | 1.378 (3) | N3—H5N | 0.88 (3) |
C7—N1 | 1.367 (3) | C15—O2 | 1.244 (2) |
C7—C8 | 1.387 (3) | C15—O3 | 1.257 (2) |
C7—C12 | 1.418 (3) | C15—C16 | 1.499 (3) |
C8—C9 | 1.374 (3) | C16—H16A | 0.9600 |
C8—H8 | 0.9300 | C16—H16B | 0.9600 |
C9—C10 | 1.403 (3) | C16—H16C | 0.9600 |
| | | |
C6—C1—C12 | 107.02 (17) | C11—C10—C9 | 119.42 (18) |
C6—C1—C2 | 123.35 (18) | C11—C10—C13 | 118.00 (17) |
C12—C1—C2 | 129.62 (17) | C9—C10—C13 | 122.57 (18) |
C1—C2—C3 | 109.63 (16) | C10—C11—C12 | 120.17 (18) |
C1—C2—H2A | 109.7 | C10—C11—H11 | 119.9 |
C3—C2—H2A | 109.7 | C12—C11—H11 | 119.9 |
C1—C2—H2B | 109.7 | C11—C12—C7 | 118.75 (18) |
C3—C2—H2B | 109.7 | C11—C12—C1 | 134.93 (18) |
H2A—C2—H2B | 108.2 | C7—C12—C1 | 106.32 (16) |
N2—C3—C4 | 108.35 (17) | O1—C13—N3 | 120.42 (19) |
N2—C3—C2 | 111.01 (16) | O1—C13—C10 | 120.85 (18) |
C4—C3—C2 | 113.52 (18) | N3—C13—C10 | 118.74 (18) |
N2—C3—H3 | 107.9 | N2—C14—H14A | 109.5 |
C4—C3—H3 | 107.9 | N2—C14—H14B | 109.5 |
C2—C3—H3 | 107.9 | H14A—C14—H14B | 109.5 |
C3—C4—C5 | 111.63 (18) | N2—C14—H14C | 109.5 |
C3—C4—H4A | 109.3 | H14A—C14—H14C | 109.5 |
C5—C4—H4A | 109.3 | H14B—C14—H14C | 109.5 |
C3—C4—H4B | 109.3 | C7—N1—C6 | 108.67 (17) |
C5—C4—H4B | 109.3 | C7—N1—H1N | 127.5 (14) |
H4A—C4—H4B | 108.0 | C6—N1—H1N | 123.8 (13) |
C6—C5—C4 | 108.87 (16) | C14—N2—C3 | 115.08 (18) |
C6—C5—H5A | 109.9 | C14—N2—H2N | 107.5 (13) |
C4—C5—H5A | 109.9 | C3—N2—H2N | 109.6 (13) |
C6—C5—H5B | 109.9 | C14—N2—H3N | 106.3 (14) |
C4—C5—H5B | 109.9 | C3—N2—H3N | 110.0 (14) |
H5A—C5—H5B | 108.3 | H2N—N2—H3N | 108 (2) |
C1—C6—N1 | 110.15 (18) | C13—N3—H4N | 123.5 (15) |
C1—C6—C5 | 125.95 (18) | C13—N3—H5N | 116.6 (16) |
N1—C6—C5 | 123.90 (17) | H4N—N3—H5N | 118 (2) |
N1—C7—C8 | 130.57 (19) | O2—C15—O3 | 123.4 (2) |
N1—C7—C12 | 107.82 (17) | O2—C15—C16 | 118.8 (2) |
C8—C7—C12 | 121.60 (18) | O3—C15—C16 | 117.8 (2) |
C9—C8—C7 | 117.79 (19) | C15—C16—H16A | 109.5 |
C9—C8—H8 | 121.1 | C15—C16—H16B | 109.5 |
C7—C8—H8 | 121.1 | H16A—C16—H16B | 109.5 |
C8—C9—C10 | 122.19 (19) | C15—C16—H16C | 109.5 |
C8—C9—H9 | 118.9 | H16A—C16—H16C | 109.5 |
C10—C9—H9 | 118.9 | H16B—C16—H16C | 109.5 |
| | | |
C6—C1—C2—C3 | −13.2 (3) | C10—C11—C12—C7 | −1.9 (3) |
C12—C1—C2—C3 | 168.2 (2) | C10—C11—C12—C1 | 178.0 (2) |
C1—C2—C3—N2 | 164.77 (18) | N1—C7—C12—C11 | −178.25 (19) |
C1—C2—C3—C4 | 42.4 (3) | C8—C7—C12—C11 | 3.2 (3) |
N2—C3—C4—C5 | 174.42 (18) | N1—C7—C12—C1 | 1.8 (2) |
C2—C3—C4—C5 | −61.8 (2) | C8—C7—C12—C1 | −176.8 (2) |
C3—C4—C5—C6 | 45.9 (3) | C6—C1—C12—C11 | 178.9 (2) |
C12—C1—C6—N1 | 0.1 (3) | C2—C1—C12—C11 | −2.4 (4) |
C2—C1—C6—N1 | −178.69 (19) | C6—C1—C12—C7 | −1.2 (2) |
C12—C1—C6—C5 | −179.5 (2) | C2—C1—C12—C7 | 177.6 (2) |
C2—C1—C6—C5 | 1.7 (4) | C11—C10—C13—O1 | −1.9 (3) |
C4—C5—C6—C1 | −17.9 (3) | C9—C10—C13—O1 | 179.2 (2) |
C4—C5—C6—N1 | 162.5 (2) | C11—C10—C13—N3 | 177.85 (19) |
N1—C7—C8—C9 | −179.9 (2) | C9—C10—C13—N3 | −1.1 (3) |
C12—C7—C8—C9 | −1.7 (3) | C8—C7—N1—C6 | 176.7 (2) |
C7—C8—C9—C10 | −0.9 (4) | C12—C7—N1—C6 | −1.7 (2) |
C8—C9—C10—C11 | 2.1 (3) | C1—C6—N1—C7 | 1.0 (3) |
C8—C9—C10—C13 | −179.0 (2) | C5—C6—N1—C7 | −179.4 (2) |
C9—C10—C11—C12 | −0.6 (3) | C4—C3—N2—C14 | −179.59 (19) |
C13—C10—C11—C12 | −179.59 (18) | C2—C3—N2—C14 | 55.1 (3) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1N···O3i | 0.90 (2) | 1.92 (2) | 2.811 (2) | 173 (2) |
N2—H2N···O2 | 0.94 (2) | 1.86 (2) | 2.782 (2) | 167 (2) |
N2—H3N···O3ii | 0.99 (3) | 1.74 (3) | 2.709 (3) | 164 (2) |
N3—H4N···O1iii | 0.86 (2) | 2.12 (3) | 2.950 (3) | 163 (2) |
N3—H5N···O2iv | 0.88 (3) | 2.12 (3) | 2.914 (3) | 151 (2) |
C9—H9···O1iii | 0.93 | 2.52 | 3.420 (3) | 163 |
C14—H14B···O1v | 0.96 | 2.42 | 3.310 (3) | 154 |
Symmetry codes: (i) −x+1, −y, −z+1; (ii) −x+1, −y, −z+2; (iii) x, −y+1/2, z−1/2; (iv) −x, y+1/2, −z+3/2; (v) −x, −y, −z+2. |
(II) (
R)-(+)-6-Carbamoyl-
N-methyl-2,3,4,9-tetrahydro-1
H-carbazol-3-aminium 3-carboxypropanoate monohydrate
top
Crystal data top
C14H18N3O+·C4H5O4−·H2O | F(000) = 808 |
Mr = 379.41 | Dx = 1.327 Mg m−3 |
Monoclinic, P21 | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: P 2yb | Cell parameters from 5616 reflections |
a = 10.6206 (6) Å | θ = 2.6–23.2° |
b = 7.9939 (5) Å | µ = 0.10 mm−1 |
c = 22.3916 (13) Å | T = 294 K |
β = 92.884 (1)° | Needle, colorless |
V = 1898.64 (19) Å3 | 0.18 × 0.11 × 0.09 mm |
Z = 4 | |
Data collection top
CCD Area Detector diffractometer | 4283 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.036 |
Graphite monochromator | θmax = 28.0°, θmin = 1.8° |
ω scan | h = −13→13 |
22400 measured reflections | k = −10→10 |
4828 independent reflections | l = −29→28 |
Refinement top
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.066 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.157 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.14 | w = 1/[σ2(Fo2) + (0.0773P)2 + 0.5607P] where P = (Fo2 + 2Fc2)/3 |
4828 reflections | (Δ/σ)max < 0.001 |
549 parameters | Δρmax = 0.31 e Å−3 |
7 restraints | Δρmin = −0.20 e Å−3 |
Special details top
Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell e.s.d.'s are taken
into account individually in the estimation of e.s.d.'s in distances, angles
and torsion angles; correlations between e.s.d.'s in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s.
planes. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
C1A | 0.8635 (3) | 0.0934 (5) | 0.22595 (14) | 0.0311 (7) | |
C2A | 0.8378 (3) | 0.1294 (5) | 0.16087 (15) | 0.0367 (8) | |
H2A | 0.8798 | 0.0477 | 0.1368 | 0.044* | |
H2B | 0.8687 | 0.2398 | 0.1512 | 0.044* | |
C3A | 0.6964 (3) | 0.1204 (5) | 0.14858 (14) | 0.0343 (7) | |
H3A | 0.6688 | 0.0054 | 0.1555 | 0.041* | |
C4A | 0.6274 (4) | 0.2366 (6) | 0.19005 (17) | 0.0444 (9) | |
H4A | 0.5384 | 0.2394 | 0.1779 | 0.053* | |
H4B | 0.6605 | 0.3492 | 0.1870 | 0.053* | |
C5A | 0.6438 (3) | 0.1762 (6) | 0.25518 (16) | 0.0450 (10) | |
H5A | 0.6278 | 0.2678 | 0.2822 | 0.054* | |
H5B | 0.5837 | 0.0878 | 0.2622 | 0.054* | |
C6A | 0.7750 (3) | 0.1124 (5) | 0.26704 (14) | 0.0340 (7) | |
C7A | 0.9414 (3) | 0.0073 (5) | 0.31718 (14) | 0.0328 (7) | |
C8A | 1.0265 (3) | −0.0580 (5) | 0.36097 (14) | 0.0350 (8) | |
H8A | 1.0046 | −0.0703 | 0.4004 | 0.042* | |
C9A | 1.1430 (3) | −0.1028 (5) | 0.34330 (15) | 0.0352 (8) | |
H9A | 1.2018 | −0.1439 | 0.3718 | 0.042* | |
C10A | 1.1774 (3) | −0.0891 (4) | 0.28353 (14) | 0.0322 (7) | |
C11A | 1.0919 (3) | −0.0259 (5) | 0.24016 (13) | 0.0304 (7) | |
H11A | 1.1138 | −0.0169 | 0.2006 | 0.036* | |
C12A | 0.9725 (3) | 0.0241 (4) | 0.25688 (13) | 0.0308 (7) | |
C13A | 1.3066 (3) | −0.1432 (5) | 0.26977 (15) | 0.0336 (7) | |
C14A | 0.5343 (5) | 0.1177 (11) | 0.0634 (2) | 0.088 (2) | |
H14A | 0.5247 | −0.0012 | 0.0670 | 0.132* | |
H14B | 0.5206 | 0.1496 | 0.0222 | 0.132* | |
H14C | 0.4740 | 0.1732 | 0.0870 | 0.132* | |
N1A | 0.8218 (3) | 0.0626 (4) | 0.32229 (13) | 0.0379 (7) | |
H1N | 0.786 (4) | 0.057 (7) | 0.353 (2) | 0.051 (13)* | |
N2A | 0.6626 (4) | 0.1661 (6) | 0.08462 (15) | 0.0493 (9) | |
H2N | 0.707 (4) | 0.112 (6) | 0.0641 (19) | 0.040 (12)* | |
H3N | 0.668 (5) | 0.279 (10) | 0.077 (2) | 0.080 (19)* | |
N3A | 1.3450 (3) | −0.1274 (5) | 0.21518 (15) | 0.0455 (9) | |
H4N | 1.291 (3) | −0.111 (5) | 0.1859 (17) | 0.033 (10)* | |
H5N | 1.411 (4) | −0.169 (5) | 0.2071 (16) | 0.030 (10)* | |
O1A | 1.3794 (2) | −0.2009 (4) | 0.31050 (11) | 0.0435 (7) | |
C1B | 2.1091 (3) | −0.5282 (5) | 0.28177 (14) | 0.0318 (7) | |
C2B | 2.1199 (3) | −0.5905 (5) | 0.34470 (16) | 0.0388 (8) | |
H2C | 2.0705 | −0.6919 | 0.3477 | 0.047* | |
H2D | 2.0854 | −0.5074 | 0.3709 | 0.047* | |
C3B | 2.2574 (3) | −0.6272 (5) | 0.36553 (16) | 0.0373 (8) | |
H3B | 2.2565 | −0.7065 | 0.3989 | 0.045* | |
C4B | 2.3316 (4) | −0.7059 (6) | 0.31623 (19) | 0.0462 (9) | |
H4C | 2.2959 | −0.8150 | 0.3068 | 0.055* | |
H4D | 2.4178 | −0.7229 | 0.3314 | 0.055* | |
C5B | 2.3333 (3) | −0.6036 (6) | 0.25862 (17) | 0.0438 (9) | |
H5C | 2.3929 | −0.5121 | 0.2638 | 0.053* | |
H5D | 2.3599 | −0.6738 | 0.2262 | 0.053* | |
C6B | 2.2046 (3) | −0.5361 (5) | 0.24360 (15) | 0.0358 (7) | |
C7B | 2.0412 (3) | −0.4282 (5) | 0.19026 (15) | 0.0366 (8) | |
C8B | 1.9594 (3) | −0.3612 (5) | 0.14621 (15) | 0.0407 (9) | |
H8B | 1.9859 | −0.3411 | 0.1079 | 0.049* | |
C9B | 1.8383 (3) | −0.3254 (5) | 0.16074 (16) | 0.0383 (8) | |
H9B | 1.7820 | −0.2812 | 0.1317 | 0.046* | |
C10B | 1.7975 (3) | −0.3544 (5) | 0.21903 (15) | 0.0347 (8) | |
C11B | 1.8798 (3) | −0.4203 (5) | 0.26287 (15) | 0.0331 (7) | |
H11B | 1.8533 | −0.4380 | 0.3013 | 0.040* | |
C12B | 2.0026 (3) | −0.4598 (5) | 0.24892 (14) | 0.0319 (7) | |
C13B | 1.6661 (3) | −0.3069 (5) | 0.23125 (15) | 0.0351 (7) | |
C14B | 2.4459 (4) | −0.4869 (8) | 0.4164 (2) | 0.0679 (15) | |
H14D | 2.4476 | −0.5799 | 0.4436 | 0.102* | |
H14E | 2.4688 | −0.3866 | 0.4379 | 0.102* | |
H14F | 2.5046 | −0.5064 | 0.3860 | 0.102* | |
N1B | 2.1634 (3) | −0.4755 (5) | 0.18869 (13) | 0.0414 (8) | |
H6N | 2.201 (3) | −0.470 (5) | 0.1611 (16) | 0.023 (9)* | |
N2B | 2.3170 (3) | −0.4684 (5) | 0.38836 (14) | 0.0396 (7) | |
H7N | 2.314 (4) | −0.386 (6) | 0.3552 (19) | 0.043 (11)* | |
H8N | 2.266 (4) | −0.431 (6) | 0.4148 (18) | 0.041 (11)* | |
N3B | 1.6348 (3) | −0.2953 (6) | 0.28742 (14) | 0.0476 (9) | |
H9N | 1.688 (4) | −0.305 (6) | 0.3166 (19) | 0.042 (11)* | |
H10N | 1.560 (3) | −0.261 (5) | 0.2944 (14) | 0.020 (8)* | |
O1B | 1.5863 (2) | −0.2804 (4) | 0.18935 (11) | 0.0489 (7) | |
C15A | 0.7918 (5) | 0.6803 (5) | 0.45505 (17) | 0.0467 (10) | |
C16A | 0.8210 (7) | 0.5154 (6) | 0.4830 (2) | 0.085 (2) | |
H16A | 0.9086 | 0.5155 | 0.4975 | 0.102* | |
H16B | 0.7699 | 0.5024 | 0.5174 | 0.102* | |
C17A | 0.7996 (5) | 0.3689 (6) | 0.44335 (19) | 0.0561 (12) | |
H17A | 0.8695 | 0.3606 | 0.4172 | 0.067* | |
H17B | 0.7238 | 0.3884 | 0.4183 | 0.067* | |
C18A | 0.7863 (4) | 0.2048 (5) | 0.47491 (16) | 0.0387 (8) | |
O2A | 0.8080 (5) | 0.8052 (4) | 0.49195 (14) | 0.0844 (14) | |
H2O | 0.789 (5) | 0.902 (7) | 0.468 (2) | 0.067 (15)* | |
O3A | 0.7602 (4) | 0.6985 (4) | 0.40403 (13) | 0.0682 (10) | |
O4A | 0.8123 (3) | 0.1958 (4) | 0.52874 (12) | 0.0602 (8) | |
O5A | 0.7483 (3) | 0.0822 (4) | 0.44293 (12) | 0.0567 (8) | |
C15B | 2.1965 (4) | −1.0427 (6) | 0.04967 (17) | 0.0469 (10) | |
C16B | 2.1708 (8) | −0.8816 (7) | 0.0186 (2) | 0.095 (2) | |
H16C | 2.0878 | −0.8868 | −0.0015 | 0.114* | |
H16D | 2.2318 | −0.8665 | −0.0117 | 0.114* | |
C17B | 2.1760 (6) | −0.7325 (6) | 0.0594 (2) | 0.0713 (16) | |
H17C | 2.0943 | −0.7193 | 0.0763 | 0.086* | |
H17D | 2.2370 | −0.7547 | 0.0921 | 0.086* | |
C18B | 2.2101 (4) | −0.5721 (5) | 0.03051 (17) | 0.0418 (9) | |
O2B | 2.1967 (6) | −1.1716 (5) | 0.01417 (18) | 0.0932 (16) | |
H3O | 2.217 (7) | −1.260 (11) | 0.029 (3) | 0.11 (3)* | |
O3B | 2.2174 (4) | −1.0554 (5) | 0.10135 (14) | 0.0822 (12) | |
O4B | 2.2036 (4) | −0.5605 (5) | −0.02416 (13) | 0.0746 (11) | |
O5B | 2.2468 (3) | −0.4550 (4) | 0.06510 (13) | 0.0599 (8) | |
O1W | 2.5350 (5) | −0.4752 (8) | 0.08517 (19) | 0.1043 (16) | |
H1W | 2.564 (5) | −0.399 (7) | 0.112 (3) | 0.125* | |
H2W | 2.4505 (11) | −0.471 (10) | 0.086 (3) | 0.125* | |
O2W | 0.4732 (6) | 0.0040 (13) | 0.4208 (3) | 0.153 (3) | |
H3W | 0.5572 (13) | 0.007 (17) | 0.421 (4) | 0.184* | |
H4W | 0.445 (7) | −0.034 (14) | 0.385 (2) | 0.184* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
C1A | 0.0305 (15) | 0.0362 (18) | 0.0264 (15) | 0.0028 (14) | 0.0001 (12) | −0.0024 (13) |
C2A | 0.0347 (17) | 0.044 (2) | 0.0310 (16) | 0.0097 (15) | 0.0021 (13) | 0.0036 (15) |
C3A | 0.0347 (16) | 0.041 (2) | 0.0267 (15) | 0.0073 (15) | −0.0015 (13) | 0.0005 (14) |
C4A | 0.0377 (18) | 0.053 (2) | 0.042 (2) | 0.0205 (17) | −0.0030 (15) | −0.0045 (18) |
C5A | 0.0358 (17) | 0.067 (3) | 0.0327 (18) | 0.0183 (19) | 0.0051 (14) | −0.0062 (18) |
C6A | 0.0347 (16) | 0.0376 (19) | 0.0297 (16) | 0.0070 (15) | 0.0011 (13) | −0.0039 (14) |
C7A | 0.0325 (16) | 0.0376 (19) | 0.0283 (15) | 0.0003 (14) | 0.0030 (12) | −0.0034 (14) |
C8A | 0.0402 (18) | 0.043 (2) | 0.0215 (14) | 0.0008 (15) | 0.0000 (13) | 0.0000 (14) |
C9A | 0.0374 (18) | 0.040 (2) | 0.0270 (16) | 0.0036 (15) | −0.0065 (13) | 0.0023 (15) |
C10A | 0.0343 (17) | 0.0322 (17) | 0.0298 (16) | −0.0002 (14) | −0.0013 (13) | 0.0007 (13) |
C11A | 0.0285 (15) | 0.0394 (18) | 0.0231 (14) | 0.0010 (14) | −0.0008 (12) | 0.0003 (13) |
C12A | 0.0363 (17) | 0.0333 (17) | 0.0225 (14) | −0.0014 (14) | −0.0024 (12) | −0.0007 (13) |
C13A | 0.0256 (15) | 0.0387 (19) | 0.0359 (17) | −0.0004 (13) | −0.0035 (13) | 0.0018 (15) |
C14A | 0.061 (3) | 0.144 (6) | 0.055 (3) | 0.018 (4) | −0.026 (2) | −0.029 (4) |
N1A | 0.0388 (16) | 0.0493 (19) | 0.0259 (14) | 0.0045 (14) | 0.0048 (12) | −0.0037 (13) |
N2A | 0.053 (2) | 0.063 (3) | 0.0310 (16) | 0.0178 (19) | −0.0057 (14) | −0.0017 (16) |
N3A | 0.0286 (15) | 0.071 (2) | 0.0367 (17) | 0.0131 (16) | 0.0007 (13) | 0.0075 (17) |
O1A | 0.0311 (12) | 0.0641 (18) | 0.0351 (13) | 0.0101 (12) | −0.0018 (10) | 0.0066 (13) |
C1B | 0.0281 (15) | 0.0341 (17) | 0.0334 (16) | −0.0010 (14) | 0.0032 (13) | −0.0046 (14) |
C2B | 0.0327 (17) | 0.049 (2) | 0.0350 (18) | 0.0028 (16) | 0.0055 (14) | 0.0016 (16) |
C3B | 0.0398 (18) | 0.037 (2) | 0.0352 (17) | 0.0042 (15) | 0.0019 (14) | 0.0068 (15) |
C4B | 0.043 (2) | 0.039 (2) | 0.057 (2) | 0.0117 (17) | 0.0020 (17) | −0.0052 (19) |
C5B | 0.0333 (18) | 0.055 (2) | 0.044 (2) | 0.0104 (17) | 0.0085 (15) | −0.0136 (18) |
C6B | 0.0328 (16) | 0.0412 (19) | 0.0336 (17) | −0.0033 (15) | 0.0045 (13) | −0.0118 (15) |
C7B | 0.0349 (17) | 0.043 (2) | 0.0323 (17) | −0.0049 (15) | 0.0075 (13) | −0.0103 (15) |
C8B | 0.0458 (19) | 0.053 (2) | 0.0232 (15) | −0.0042 (17) | 0.0038 (14) | −0.0005 (15) |
C9B | 0.0413 (18) | 0.043 (2) | 0.0302 (17) | 0.0018 (16) | −0.0043 (14) | −0.0023 (15) |
C10B | 0.0302 (16) | 0.0384 (19) | 0.0355 (17) | −0.0019 (14) | 0.0007 (13) | −0.0060 (14) |
C11B | 0.0289 (16) | 0.0410 (19) | 0.0293 (15) | −0.0021 (14) | 0.0021 (12) | −0.0012 (14) |
C12B | 0.0332 (16) | 0.0338 (18) | 0.0286 (16) | −0.0040 (14) | −0.0005 (13) | −0.0040 (14) |
C13B | 0.0268 (15) | 0.041 (2) | 0.0369 (17) | −0.0034 (14) | −0.0025 (13) | −0.0053 (16) |
C14B | 0.046 (2) | 0.092 (4) | 0.064 (3) | −0.001 (3) | −0.017 (2) | 0.006 (3) |
N1B | 0.0375 (16) | 0.060 (2) | 0.0278 (15) | −0.0010 (15) | 0.0120 (13) | −0.0076 (15) |
N2B | 0.0432 (17) | 0.0451 (18) | 0.0303 (14) | 0.0056 (14) | 0.0007 (13) | 0.0030 (14) |
N3B | 0.0277 (15) | 0.080 (3) | 0.0350 (16) | 0.0112 (17) | −0.0004 (13) | −0.0046 (18) |
O1B | 0.0338 (13) | 0.074 (2) | 0.0385 (14) | 0.0077 (14) | −0.0053 (11) | −0.0042 (14) |
C15A | 0.077 (3) | 0.033 (2) | 0.0296 (18) | −0.0066 (19) | −0.0014 (17) | 0.0016 (15) |
C16A | 0.174 (6) | 0.030 (2) | 0.046 (3) | −0.004 (3) | −0.039 (3) | 0.0034 (19) |
C17A | 0.092 (3) | 0.037 (2) | 0.039 (2) | −0.004 (2) | 0.000 (2) | 0.0031 (17) |
C18A | 0.056 (2) | 0.0314 (18) | 0.0301 (17) | 0.0003 (17) | 0.0158 (15) | −0.0019 (15) |
O2A | 0.185 (4) | 0.0330 (17) | 0.0342 (16) | −0.003 (2) | −0.006 (2) | 0.0019 (13) |
O3A | 0.120 (3) | 0.0433 (18) | 0.0390 (16) | 0.001 (2) | −0.0224 (17) | 0.0029 (14) |
O4A | 0.106 (2) | 0.0444 (17) | 0.0308 (13) | −0.0163 (18) | 0.0061 (14) | 0.0048 (13) |
O5A | 0.100 (2) | 0.0350 (15) | 0.0362 (14) | −0.0058 (16) | 0.0127 (15) | −0.0042 (12) |
C15B | 0.067 (3) | 0.042 (2) | 0.0315 (19) | −0.008 (2) | −0.0011 (17) | 0.0040 (17) |
C16B | 0.198 (7) | 0.041 (3) | 0.041 (3) | −0.008 (4) | −0.029 (3) | 0.006 (2) |
C17B | 0.135 (5) | 0.042 (3) | 0.037 (2) | −0.005 (3) | 0.011 (3) | 0.0016 (19) |
C18B | 0.045 (2) | 0.049 (2) | 0.0322 (18) | −0.0004 (17) | 0.0096 (15) | 0.0018 (16) |
O2B | 0.198 (5) | 0.036 (2) | 0.0445 (19) | −0.004 (2) | 0.001 (2) | 0.0024 (15) |
O3B | 0.147 (4) | 0.061 (2) | 0.0374 (17) | 0.019 (2) | −0.0142 (19) | 0.0044 (16) |
O4B | 0.116 (3) | 0.069 (2) | 0.0383 (16) | −0.034 (2) | 0.0053 (17) | 0.0054 (16) |
O5B | 0.099 (2) | 0.0409 (17) | 0.0408 (15) | −0.0037 (17) | 0.0136 (15) | 0.0002 (13) |
O1W | 0.121 (4) | 0.118 (4) | 0.071 (3) | 0.001 (3) | −0.027 (3) | −0.022 (3) |
O2W | 0.119 (4) | 0.200 (8) | 0.137 (5) | 0.001 (6) | −0.027 (4) | −0.050 (6) |
Geometric parameters (Å, º) top
C1A—C6A | 1.356 (5) | C5B—H5D | 0.9700 |
C1A—C12A | 1.431 (4) | C6B—N1B | 1.372 (5) |
C1A—C2A | 1.497 (4) | C7B—N1B | 1.354 (5) |
C2A—C3A | 1.514 (5) | C7B—C8B | 1.389 (5) |
C2A—H2A | 0.9700 | C7B—C12B | 1.418 (4) |
C2A—H2B | 0.9700 | C8B—C9B | 1.373 (5) |
C3A—N2A | 1.504 (5) | C8B—H8B | 0.9300 |
C3A—C4A | 1.527 (5) | C9B—C10B | 1.415 (5) |
C3A—H3A | 0.9800 | C9B—H9B | 0.9300 |
C4A—C5A | 1.538 (5) | C10B—C11B | 1.385 (5) |
C4A—H4A | 0.9700 | C10B—C13B | 1.486 (5) |
C4A—H4B | 0.9700 | C11B—C12B | 1.392 (4) |
C5A—C6A | 1.495 (5) | C11B—H11B | 0.9300 |
C5A—H5A | 0.9700 | C13B—O1B | 1.250 (4) |
C5A—H5B | 0.9700 | C13B—N3B | 1.320 (5) |
C6A—N1A | 1.369 (4) | C14B—N2B | 1.485 (5) |
C7A—N1A | 1.355 (4) | C14B—H14D | 0.9600 |
C7A—C8A | 1.400 (5) | C14B—H14E | 0.9600 |
C7A—C12A | 1.412 (4) | C14B—H14F | 0.9600 |
C8A—C9A | 1.366 (5) | N1B—H6N | 0.75 (3) |
C8A—H8A | 0.9300 | N2B—H7N | 0.99 (5) |
C9A—C10A | 1.409 (5) | N2B—H8N | 0.88 (4) |
C9A—H9A | 0.9300 | N3B—H9N | 0.85 (4) |
C10A—C11A | 1.391 (4) | N3B—H10N | 0.86 (3) |
C10A—C13A | 1.486 (4) | C15A—O3A | 1.183 (5) |
C11A—C12A | 1.398 (5) | C15A—O2A | 1.302 (5) |
C11A—H11A | 0.9300 | C15A—C16A | 1.486 (6) |
C13A—O1A | 1.253 (4) | C16A—C17A | 1.481 (6) |
C13A—N3A | 1.314 (5) | C16A—H16A | 0.9700 |
C14A—N2A | 1.472 (7) | C16A—H16B | 0.9700 |
C14A—H14A | 0.9600 | C17A—C18A | 1.500 (6) |
C14A—H14B | 0.9600 | C17A—H17A | 0.9700 |
C14A—H14C | 0.9600 | C17A—H17B | 0.9700 |
N1A—H1N | 0.81 (5) | C18A—O4A | 1.225 (5) |
N2A—H2N | 0.80 (5) | C18A—O5A | 1.268 (5) |
N2A—H3N | 0.92 (7) | O2A—H2O | 0.96 (6) |
N3A—H4N | 0.86 (4) | C15B—O3B | 1.172 (5) |
N3A—H5N | 0.81 (4) | C15B—O2B | 1.302 (6) |
C1B—C6B | 1.360 (5) | C15B—C16B | 1.483 (7) |
C1B—C12B | 1.427 (5) | C16B—C17B | 1.501 (7) |
C1B—C2B | 1.494 (5) | C16B—H16C | 0.9700 |
C2B—C3B | 1.538 (5) | C16B—H16D | 0.9700 |
C2B—H2C | 0.9700 | C17B—C18B | 1.489 (6) |
C2B—H2D | 0.9700 | C17B—H17C | 0.9700 |
C3B—N2B | 1.497 (5) | C17B—H17D | 0.9700 |
C3B—C4B | 1.524 (5) | C18B—O4B | 1.226 (5) |
C3B—H3B | 0.9800 | C18B—O5B | 1.264 (5) |
C4B—C5B | 1.528 (6) | O2B—H3O | 0.81 (9) |
C4B—H4C | 0.9700 | O1W—H1W | 0.896 (10) |
C4B—H4D | 0.9700 | O1W—H2W | 0.899 (10) |
C5B—C6B | 1.493 (5) | O2W—H3W | 0.893 (11) |
C5B—H5C | 0.9700 | O2W—H4W | 0.893 (11) |
| | | |
C6A—C1A—C12A | 106.7 (3) | H4C—C4B—H4D | 107.5 |
C6A—C1A—C2A | 122.7 (3) | C6B—C5B—C4B | 109.5 (3) |
C12A—C1A—C2A | 130.5 (3) | C6B—C5B—H5C | 109.8 |
C1A—C2A—C3A | 107.3 (3) | C4B—C5B—H5C | 109.8 |
C1A—C2A—H2A | 110.2 | C6B—C5B—H5D | 109.8 |
C3A—C2A—H2A | 110.2 | C4B—C5B—H5D | 109.8 |
C1A—C2A—H2B | 110.2 | H5C—C5B—H5D | 108.2 |
C3A—C2A—H2B | 110.2 | C1B—C6B—N1B | 109.5 (3) |
H2A—C2A—H2B | 108.5 | C1B—C6B—C5B | 125.3 (3) |
N2A—C3A—C2A | 110.4 (3) | N1B—C6B—C5B | 125.2 (3) |
N2A—C3A—C4A | 109.4 (3) | N1B—C7B—C8B | 131.0 (3) |
C2A—C3A—C4A | 111.3 (3) | N1B—C7B—C12B | 107.3 (3) |
N2A—C3A—H3A | 108.6 | C8B—C7B—C12B | 121.8 (3) |
C2A—C3A—H3A | 108.6 | C9B—C8B—C7B | 118.2 (3) |
C4A—C3A—H3A | 108.6 | C9B—C8B—H8B | 120.9 |
C3A—C4A—C5A | 110.5 (3) | C7B—C8B—H8B | 120.9 |
C3A—C4A—H4A | 109.5 | C8B—C9B—C10B | 121.2 (3) |
C5A—C4A—H4A | 109.5 | C8B—C9B—H9B | 119.4 |
C3A—C4A—H4B | 109.5 | C10B—C9B—H9B | 119.4 |
C5A—C4A—H4B | 109.5 | C11B—C10B—C9B | 120.3 (3) |
H4A—C4A—H4B | 108.1 | C11B—C10B—C13B | 122.1 (3) |
C6A—C5A—C4A | 109.6 (3) | C9B—C10B—C13B | 117.5 (3) |
C6A—C5A—H5A | 109.7 | C10B—C11B—C12B | 119.5 (3) |
C4A—C5A—H5A | 109.7 | C10B—C11B—H11B | 120.3 |
C6A—C5A—H5B | 109.7 | C12B—C11B—H11B | 120.3 |
C4A—C5A—H5B | 109.7 | C11B—C12B—C7B | 119.0 (3) |
H5A—C5A—H5B | 108.2 | C11B—C12B—C1B | 134.3 (3) |
C1A—C6A—N1A | 110.3 (3) | C7B—C12B—C1B | 106.6 (3) |
C1A—C6A—C5A | 126.1 (3) | O1B—C13B—N3B | 120.6 (3) |
N1A—C6A—C5A | 123.6 (3) | O1B—C13B—C10B | 120.9 (3) |
N1A—C7A—C8A | 129.6 (3) | N3B—C13B—C10B | 118.5 (3) |
N1A—C7A—C12A | 108.4 (3) | N2B—C14B—H14D | 109.5 |
C8A—C7A—C12A | 122.1 (3) | N2B—C14B—H14E | 109.5 |
C9A—C8A—C7A | 117.2 (3) | H14D—C14B—H14E | 109.5 |
C9A—C8A—H8A | 121.4 | N2B—C14B—H14F | 109.5 |
C7A—C8A—H8A | 121.4 | H14D—C14B—H14F | 109.5 |
C8A—C9A—C10A | 122.5 (3) | H14E—C14B—H14F | 109.5 |
C8A—C9A—H9A | 118.8 | C7B—N1B—C6B | 109.7 (3) |
C10A—C9A—H9A | 118.8 | C7B—N1B—H6N | 124 (3) |
C11A—C10A—C9A | 120.0 (3) | C6B—N1B—H6N | 127 (3) |
C11A—C10A—C13A | 122.6 (3) | C14B—N2B—C3B | 115.1 (4) |
C9A—C10A—C13A | 117.4 (3) | C14B—N2B—H7N | 112 (2) |
C10A—C11A—C12A | 119.1 (3) | C3B—N2B—H7N | 108 (2) |
C10A—C11A—H11A | 120.5 | C14B—N2B—H8N | 110 (3) |
C12A—C11A—H11A | 120.5 | C3B—N2B—H8N | 105 (3) |
C11A—C12A—C7A | 119.2 (3) | H7N—N2B—H8N | 107 (4) |
C11A—C12A—C1A | 134.7 (3) | C13B—N3B—H9N | 123 (3) |
C7A—C12A—C1A | 106.1 (3) | C13B—N3B—H10N | 118 (2) |
O1A—C13A—N3A | 120.2 (3) | H9N—N3B—H10N | 118 (4) |
O1A—C13A—C10A | 119.9 (3) | O3A—C15A—O2A | 122.7 (4) |
N3A—C13A—C10A | 119.8 (3) | O3A—C15A—C16A | 124.0 (4) |
N2A—C14A—H14A | 109.5 | O2A—C15A—C16A | 113.2 (3) |
N2A—C14A—H14B | 109.5 | C17A—C16A—C15A | 115.2 (4) |
H14A—C14A—H14B | 109.5 | C17A—C16A—H16A | 108.5 |
N2A—C14A—H14C | 109.5 | C15A—C16A—H16A | 108.5 |
H14A—C14A—H14C | 109.5 | C17A—C16A—H16B | 108.5 |
H14B—C14A—H14C | 109.5 | C15A—C16A—H16B | 108.5 |
C7A—N1A—C6A | 108.6 (3) | H16A—C16A—H16B | 107.5 |
C7A—N1A—H1N | 122 (3) | C16A—C17A—C18A | 115.1 (4) |
C6A—N1A—H1N | 129 (3) | C16A—C17A—H17A | 108.5 |
C14A—N2A—C3A | 114.6 (4) | C18A—C17A—H17A | 108.5 |
C14A—N2A—H2N | 104 (3) | C16A—C17A—H17B | 108.5 |
C3A—N2A—H2N | 107 (3) | C18A—C17A—H17B | 108.5 |
C14A—N2A—H3N | 105 (4) | H17A—C17A—H17B | 107.5 |
C3A—N2A—H3N | 113 (4) | O4A—C18A—O5A | 124.0 (4) |
H2N—N2A—H3N | 112 (5) | O4A—C18A—C17A | 119.6 (4) |
C13A—N3A—H4N | 120 (2) | O5A—C18A—C17A | 116.4 (3) |
C13A—N3A—H5N | 119 (3) | C15A—O2A—H2O | 105 (3) |
H4N—N3A—H5N | 117 (4) | O3B—C15B—O2B | 121.9 (4) |
C6B—C1B—C12B | 106.9 (3) | O3B—C15B—C16B | 124.1 (4) |
C6B—C1B—C2B | 123.6 (3) | O2B—C15B—C16B | 114.0 (4) |
C12B—C1B—C2B | 129.4 (3) | C15B—C16B—C17B | 113.8 (4) |
C1B—C2B—C3B | 112.1 (3) | C15B—C16B—H16C | 108.8 |
C1B—C2B—H2C | 109.2 | C17B—C16B—H16C | 108.8 |
C3B—C2B—H2C | 109.2 | C15B—C16B—H16D | 108.8 |
C1B—C2B—H2D | 109.2 | C17B—C16B—H16D | 108.8 |
C3B—C2B—H2D | 109.2 | H16C—C16B—H16D | 107.7 |
H2C—C2B—H2D | 107.9 | C18B—C17B—C16B | 115.0 (4) |
N2B—C3B—C4B | 111.9 (3) | C18B—C17B—H17C | 108.5 |
N2B—C3B—C2B | 108.7 (3) | C16B—C17B—H17C | 108.5 |
C4B—C3B—C2B | 112.1 (3) | C18B—C17B—H17D | 108.5 |
N2B—C3B—H3B | 108.0 | C16B—C17B—H17D | 108.5 |
C4B—C3B—H3B | 108.0 | H17C—C17B—H17D | 107.5 |
C2B—C3B—H3B | 108.0 | O4B—C18B—O5B | 123.8 (4) |
C3B—C4B—C5B | 114.8 (3) | O4B—C18B—C17B | 119.7 (4) |
C3B—C4B—H4C | 108.6 | O5B—C18B—C17B | 116.5 (4) |
C5B—C4B—H4C | 108.6 | C15B—O2B—H3O | 116 (5) |
C3B—C4B—H4D | 108.6 | H1W—O1W—H2W | 106.0 (17) |
C5B—C4B—H4D | 108.6 | H3W—O2W—H4W | 107.6 (17) |
| | | |
C6A—C1A—C2A—C3A | −21.6 (5) | C2B—C3B—C4B—C5B | 56.5 (5) |
C12A—C1A—C2A—C3A | 153.0 (4) | C3B—C4B—C5B—C6B | −42.9 (5) |
C1A—C2A—C3A—N2A | 176.4 (3) | C12B—C1B—C6B—N1B | 0.3 (4) |
C1A—C2A—C3A—C4A | 54.7 (4) | C2B—C1B—C6B—N1B | 177.5 (3) |
N2A—C3A—C4A—C5A | 171.3 (3) | C12B—C1B—C6B—C5B | −178.5 (4) |
C2A—C3A—C4A—C5A | −66.5 (4) | C2B—C1B—C6B—C5B | −1.3 (6) |
C3A—C4A—C5A—C6A | 38.7 (5) | C4B—C5B—C6B—C1B | 15.8 (6) |
C12A—C1A—C6A—N1A | 1.2 (4) | C4B—C5B—C6B—N1B | −162.8 (4) |
C2A—C1A—C6A—N1A | 176.9 (3) | N1B—C7B—C8B—C9B | 179.7 (4) |
C12A—C1A—C6A—C5A | −178.1 (4) | C12B—C7B—C8B—C9B | 0.0 (6) |
C2A—C1A—C6A—C5A | −2.4 (6) | C7B—C8B—C9B—C10B | 0.5 (6) |
C4A—C5A—C6A—C1A | −6.3 (6) | C8B—C9B—C10B—C11B | −0.1 (6) |
C4A—C5A—C6A—N1A | 174.4 (4) | C8B—C9B—C10B—C13B | 178.1 (4) |
N1A—C7A—C8A—C9A | −179.2 (4) | C9B—C10B—C11B—C12B | −0.8 (5) |
C12A—C7A—C8A—C9A | 1.1 (6) | C13B—C10B—C11B—C12B | −178.9 (4) |
C7A—C8A—C9A—C10A | −1.5 (6) | C10B—C11B—C12B—C7B | 1.3 (5) |
C8A—C9A—C10A—C11A | 0.9 (6) | C10B—C11B—C12B—C1B | −179.7 (4) |
C8A—C9A—C10A—C13A | −179.5 (4) | N1B—C7B—C12B—C11B | 179.4 (3) |
C9A—C10A—C11A—C12A | 0.3 (5) | C8B—C7B—C12B—C11B | −0.9 (6) |
C13A—C10A—C11A—C12A | −179.3 (3) | N1B—C7B—C12B—C1B | 0.1 (4) |
C10A—C11A—C12A—C7A | −0.7 (5) | C8B—C7B—C12B—C1B | 179.8 (4) |
C10A—C11A—C12A—C1A | 179.7 (4) | C6B—C1B—C12B—C11B | −179.4 (4) |
N1A—C7A—C12A—C11A | −179.7 (3) | C2B—C1B—C12B—C11B | 3.7 (7) |
C8A—C7A—C12A—C11A | 0.0 (5) | C6B—C1B—C12B—C7B | −0.2 (4) |
N1A—C7A—C12A—C1A | 0.0 (4) | C2B—C1B—C12B—C7B | −177.2 (4) |
C8A—C7A—C12A—C1A | 179.7 (3) | C11B—C10B—C13B—O1B | −165.3 (4) |
C6A—C1A—C12A—C11A | 178.9 (4) | C9B—C10B—C13B—O1B | 16.6 (6) |
C2A—C1A—C12A—C11A | 3.7 (7) | C11B—C10B—C13B—N3B | 13.9 (6) |
C6A—C1A—C12A—C7A | −0.7 (4) | C9B—C10B—C13B—N3B | −164.3 (4) |
C2A—C1A—C12A—C7A | −176.0 (4) | C8B—C7B—N1B—C6B | −179.6 (4) |
C11A—C10A—C13A—O1A | −179.3 (4) | C12B—C7B—N1B—C6B | 0.1 (4) |
C9A—C10A—C13A—O1A | 1.1 (5) | C1B—C6B—N1B—C7B | −0.3 (5) |
C11A—C10A—C13A—N3A | 2.0 (6) | C5B—C6B—N1B—C7B | 178.5 (4) |
C9A—C10A—C13A—N3A | −177.6 (4) | C4B—C3B—N2B—C14B | −62.2 (4) |
C8A—C7A—N1A—C6A | −179.0 (4) | C2B—C3B—N2B—C14B | 173.5 (3) |
C12A—C7A—N1A—C6A | 0.7 (4) | O3A—C15A—C16A—C17A | −4.0 (9) |
C1A—C6A—N1A—C7A | −1.2 (4) | O2A—C15A—C16A—C17A | 177.9 (6) |
C5A—C6A—N1A—C7A | 178.1 (4) | C15A—C16A—C17A—C18A | −160.3 (5) |
C2A—C3A—N2A—C14A | 164.0 (4) | C16A—C17A—C18A—O4A | −11.0 (7) |
C4A—C3A—N2A—C14A | −73.2 (5) | C16A—C17A—C18A—O5A | 169.1 (5) |
C6B—C1B—C2B—C3B | 12.8 (5) | O3B—C15B—C16B—C17B | 1.0 (10) |
C12B—C1B—C2B—C3B | −170.6 (4) | O2B—C15B—C16B—C17B | −177.6 (6) |
C1B—C2B—C3B—N2B | 85.4 (4) | C15B—C16B—C17B—C18B | 152.9 (6) |
C1B—C2B—C3B—C4B | −38.8 (5) | C16B—C17B—C18B—O4B | 16.4 (8) |
N2B—C3B—C4B—C5B | −65.9 (4) | C16B—C17B—C18B—O5B | −162.4 (5) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N1A—H1N···O5A | 0.81 (5) | 2.08 (5) | 2.854 (4) | 161 (4) |
N2A—H2N···O4Bi | 0.80 (5) | 1.92 (5) | 2.707 (5) | 167 (5) |
N2A—H3N···O1Wii | 0.92 (7) | 2.43 (7) | 3.172 (7) | 138 (5) |
N3A—H4N···O3Biii | 0.86 (4) | 2.06 (4) | 2.884 (5) | 161 (3) |
N3A—H5N···O1B | 0.81 (4) | 2.12 (4) | 2.923 (4) | 178 (4) |
N1B—H6N···O5B | 0.75 (3) | 2.23 (4) | 2.952 (4) | 161 (3) |
N2B—H7N···O1Aiv | 0.99 (5) | 1.94 (5) | 2.858 (5) | 154 (3) |
N2B—H8N···O4Av | 0.88 (4) | 1.85 (5) | 2.703 (4) | 164 (4) |
N3B—H9N···O3Avi | 0.85 (4) | 2.07 (4) | 2.871 (4) | 159 (4) |
N3B—H10N···O1A | 0.86 (3) | 2.03 (3) | 2.887 (4) | 175 (3) |
O2A—H2O···O5Avii | 0.96 (6) | 1.60 (6) | 2.538 (5) | 167 (5) |
O2B—H3O···O5Bviii | 0.81 (9) | 1.77 (9) | 2.580 (5) | 175 (8) |
O1W—H1W···O1Biv | 0.90 (1) | 1.98 (3) | 2.835 (5) | 158 (6) |
O1W—H2W···O5B | 0.90 (1) | 2.19 (2) | 3.076 (6) | 167 (6) |
O2W—H3W···O5A | 0.89 (1) | 2.15 (3) | 3.004 (8) | 160 (9) |
O2W—H4W···O1Aix | 0.89 (1) | 2.22 (4) | 3.086 (7) | 163 (11) |
C3A—H3A···O1Bix | 0.98 | 2.57 | 3.547 (5) | 171 |
C3B—H3B···O2Ax | 0.98 | 2.57 | 3.344 (5) | 136 |
C9A—H9A···O4Axi | 0.93 | 2.58 | 3.300 (4) | 135 |
C11A—H11A···O3Biii | 0.93 | 2.55 | 3.451 (5) | 164 |
Symmetry codes: (i) −x+3, y+1/2, −z; (ii) x−2, y+1, z; (iii) x−1, y+1, z; (iv) x+1, y, z; (v) −x+3, y−1/2, −z+1; (vi) x+1, y−1, z; (vii) x, y+1, z; (viii) x, y−1, z; (ix) x−1, y, z; (x) −x+3, y−3/2, −z+1; (xi) −x+2, y−1/2, −z+1. |
(III) Bis[(
R)-(+)-6-carbamoyl-
N-methyl-2,3,4,9-tetrahydro-1
H-carbazol-3-aminium] succinate trihydrate
top
Crystal data top
2C14H18N3O+·C4H4O42−·3H2O | F(000) = 704 |
Mr = 658.75 | Dx = 1.334 Mg m−3 |
Monoclinic, P21 | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: P 2yb | Cell parameters from 8568 reflections |
a = 8.7239 (11) Å | θ = 2.2–27.2° |
b = 18.662 (2) Å | µ = 0.10 mm−1 |
c = 10.1270 (13) Å | T = 294 K |
β = 96.098 (2)° | Plate, colorless |
V = 1639.4 (4) Å3 | 0.15 × 0.14 × 0.06 mm |
Z = 2 | |
Data collection top
CCD Area Detector diffractometer | 3836 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.025 |
Graphite monochromator | θmax = 28.3°, θmin = 2.0° |
ω scan | h = −11→11 |
19224 measured reflections | k = −24→24 |
4082 independent reflections | l = −13→13 |
Refinement top
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.041 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.102 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.06 | w = 1/[σ2(Fo2) + (0.0574P)2 + 0.265P] where P = (Fo2 + 2Fc2)/3 |
4082 reflections | (Δ/σ)max < 0.001 |
490 parameters | Δρmax = 0.27 e Å−3 |
1 restraint | Δρmin = −0.22 e Å−3 |
Special details top
Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell e.s.d.'s are taken
into account individually in the estimation of e.s.d.'s in distances, angles
and torsion angles; correlations between e.s.d.'s in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s.
planes. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
C1A | −0.4446 (3) | 0.77615 (12) | 1.9076 (2) | 0.0304 (4) | |
C2A | −0.4601 (3) | 0.69807 (12) | 1.9390 (2) | 0.0334 (5) | |
H2A | −0.3717 | 0.6717 | 1.9142 | 0.040* | |
H2B | −0.5525 | 0.6785 | 1.8904 | 0.040* | |
C3A | −0.4693 (3) | 0.69225 (13) | 2.0886 (2) | 0.0320 (4) | |
H3A | −0.3725 | 0.7106 | 2.1340 | 0.038* | |
C4A | −0.6000 (3) | 0.73850 (15) | 2.1294 (3) | 0.0429 (6) | |
H4A | −0.6167 | 0.7281 | 2.2206 | 0.051* | |
H4B | −0.6943 | 0.7278 | 2.0733 | 0.051* | |
C5A | −0.5591 (3) | 0.81765 (15) | 2.1161 (2) | 0.0450 (6) | |
H5A | −0.6515 | 0.8467 | 2.1155 | 0.054* | |
H5B | −0.4876 | 0.8322 | 2.1912 | 0.054* | |
C6A | −0.4872 (3) | 0.82889 (13) | 1.9894 (2) | 0.0344 (5) | |
C7A | −0.3819 (3) | 0.88573 (12) | 1.8276 (2) | 0.0327 (4) | |
C8A | −0.3243 (3) | 0.93631 (12) | 1.7440 (2) | 0.0380 (5) | |
H8A | −0.3257 | 0.9850 | 1.7634 | 0.046* | |
C9A | −0.2654 (3) | 0.91144 (13) | 1.6315 (2) | 0.0363 (5) | |
H9A | −0.2258 | 0.9441 | 1.5747 | 0.044* | |
C10A | −0.2635 (2) | 0.83812 (12) | 1.6001 (2) | 0.0304 (4) | |
C11A | −0.3186 (2) | 0.78780 (12) | 1.6847 (2) | 0.0295 (4) | |
H11A | −0.3154 | 0.7392 | 1.6649 | 0.035* | |
C12A | −0.3789 (2) | 0.81112 (12) | 1.8000 (2) | 0.0295 (4) | |
C13A | −0.2025 (3) | 0.81756 (14) | 1.4730 (2) | 0.0339 (5) | |
C14A | −0.3432 (3) | 0.57385 (16) | 2.1367 (3) | 0.0491 (6) | |
H14A | −0.2639 | 0.5972 | 2.1942 | 0.074* | |
H14B | −0.3115 | 0.5703 | 2.0490 | 0.074* | |
H14C | −0.3605 | 0.5267 | 2.1699 | 0.074* | |
N1A | −0.4500 (3) | 0.89484 (11) | 1.9424 (2) | 0.0386 (5) | |
H1N | −0.458 (4) | 0.932 (2) | 1.987 (4) | 0.055 (9)* | |
N2A | −0.4877 (3) | 0.61616 (12) | 2.1320 (2) | 0.0377 (4) | |
H2N | −0.557 (4) | 0.5960 (18) | 2.079 (3) | 0.042 (8)* | |
H3N | −0.516 (3) | 0.6167 (17) | 2.211 (3) | 0.043 (8)* | |
N3A | −0.2314 (3) | 0.75275 (14) | 1.4222 (2) | 0.0465 (5) | |
H4N | −0.190 (4) | 0.7403 (18) | 1.349 (3) | 0.050 (9)* | |
H5N | −0.290 (4) | 0.727 (2) | 1.456 (4) | 0.065 (11)* | |
O1A | −0.1276 (2) | 0.86175 (11) | 1.41300 (18) | 0.0454 (4) | |
C1B | 0.1732 (3) | 0.83382 (13) | 0.6745 (2) | 0.0330 (5) | |
C2B | 0.2243 (3) | 0.91011 (13) | 0.6800 (2) | 0.0368 (5) | |
H2C | 0.3151 | 0.9149 | 0.7435 | 0.044* | |
H2D | 0.1435 | 0.9398 | 0.7099 | 0.044* | |
C3B | 0.2618 (3) | 0.93602 (13) | 0.5430 (2) | 0.0339 (5) | |
H3B | 0.3288 | 0.9781 | 0.5563 | 0.041* | |
C4B | 0.3465 (3) | 0.87943 (16) | 0.4701 (3) | 0.0434 (6) | |
H4C | 0.4462 | 0.8709 | 0.5197 | 0.052* | |
H4D | 0.3648 | 0.8983 | 0.3839 | 0.052* | |
C5B | 0.2624 (3) | 0.80789 (15) | 0.4496 (2) | 0.0437 (6) | |
H5C | 0.1812 | 0.8119 | 0.3767 | 0.052* | |
H5D | 0.3339 | 0.7711 | 0.4273 | 0.052* | |
C6B | 0.1949 (3) | 0.78772 (14) | 0.5737 (2) | 0.0358 (5) | |
C7B | 0.0851 (3) | 0.72234 (13) | 0.7231 (2) | 0.0353 (5) | |
C8B | 0.0208 (3) | 0.66868 (13) | 0.7962 (3) | 0.0406 (5) | |
H8B | 0.0099 | 0.6220 | 0.7643 | 0.049* | |
C9B | −0.0259 (3) | 0.68742 (14) | 0.9179 (2) | 0.0382 (5) | |
H9B | −0.0678 | 0.6524 | 0.9687 | 0.046* | |
C10B | −0.0121 (3) | 0.75785 (13) | 0.9670 (2) | 0.0320 (4) | |
C11B | 0.0521 (3) | 0.81131 (12) | 0.8943 (2) | 0.0315 (4) | |
H11B | 0.0614 | 0.8580 | 0.9264 | 0.038* | |
C12B | 0.1023 (3) | 0.79327 (12) | 0.7720 (2) | 0.0311 (4) | |
C13B | −0.0638 (3) | 0.77314 (13) | 1.1004 (2) | 0.0347 (5) | |
C14B | 0.0560 (3) | 1.02880 (17) | 0.5018 (3) | 0.0539 (7) | |
H14D | 0.1322 | 1.0652 | 0.4938 | 0.081* | |
H14E | 0.0333 | 1.0261 | 0.5924 | 0.081* | |
H14F | −0.0363 | 1.0405 | 0.4457 | 0.081* | |
N1B | 0.1411 (3) | 0.72066 (12) | 0.6011 (2) | 0.0405 (5) | |
H6N | 0.148 (4) | 0.685 (2) | 0.557 (3) | 0.053 (9)* | |
N2B | 0.1159 (2) | 0.95862 (12) | 0.4610 (2) | 0.0349 (4) | |
H7N | 0.129 (4) | 0.9635 (18) | 0.374 (3) | 0.049 (8)* | |
H8N | 0.045 (3) | 0.9270 (15) | 0.463 (3) | 0.030 (6)* | |
N3B | −0.0908 (3) | 0.84089 (14) | 1.1313 (2) | 0.0474 (5) | |
H9N | −0.087 (4) | 0.876 (2) | 1.078 (4) | 0.062 (10)* | |
H10N | −0.115 (3) | 0.8496 (18) | 1.214 (3) | 0.045 (8)* | |
O1B | −0.0814 (2) | 0.72355 (10) | 1.18003 (18) | 0.0457 (4) | |
C15 | −0.5804 (3) | 0.52770 (13) | 1.8348 (2) | 0.0354 (5) | |
C16 | −0.6405 (3) | 0.54890 (18) | 1.6945 (2) | 0.0496 (7) | |
H16A | −0.6752 | 0.5060 | 1.6460 | 0.059* | |
H16B | −0.7294 | 0.5798 | 1.6981 | 0.059* | |
C17 | −0.5267 (3) | 0.5866 (2) | 1.6192 (3) | 0.0527 (7) | |
H17A | −0.4359 | 0.5565 | 1.6196 | 0.063* | |
H17B | −0.4955 | 0.6303 | 1.6662 | 0.063* | |
C18 | −0.5816 (3) | 0.60582 (13) | 1.4753 (2) | 0.0379 (5) | |
O2 | −0.4551 (3) | 0.49700 (14) | 1.8557 (2) | 0.0637 (6) | |
O3 | −0.6627 (2) | 0.54062 (12) | 1.92618 (18) | 0.0513 (5) | |
O4 | −0.7231 (2) | 0.60742 (12) | 1.44164 (18) | 0.0498 (5) | |
O5 | −0.4786 (3) | 0.61995 (17) | 1.4030 (2) | 0.0700 (7) | |
O1W | −0.0589 (3) | 0.99504 (13) | 1.0043 (2) | 0.0516 (5) | |
H1W | −0.136 (5) | 1.011 (2) | 1.030 (4) | 0.068 (12)* | |
H2W | −0.057 (3) | 1.0184 (19) | 0.935 (4) | 0.046 (9)* | |
O2W | 0.1686 (3) | 0.9908 (2) | 1.2112 (2) | 0.0827 (10) | |
H3W | 0.099 (6) | 0.993 (3) | 1.151 (5) | 0.098 (16)* | |
H4W | 0.259 (5) | 0.993 (2) | 1.190 (4) | 0.069 (11)* | |
O3W | −0.0818 (4) | 1.09156 (15) | 0.7882 (3) | 0.0763 (8) | |
H5W | −0.151 (5) | 1.099 (2) | 0.729 (4) | 0.062 (11)* | |
H6W | −0.043 (5) | 1.135 (2) | 0.801 (4) | 0.074 (12)* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
C1A | 0.0391 (11) | 0.0295 (11) | 0.0233 (9) | 0.0009 (8) | 0.0065 (8) | 0.0005 (8) |
C2A | 0.0495 (13) | 0.0287 (10) | 0.0236 (9) | −0.0016 (9) | 0.0110 (9) | 0.0005 (8) |
C3A | 0.0385 (11) | 0.0355 (11) | 0.0226 (9) | −0.0037 (9) | 0.0064 (8) | 0.0023 (8) |
C4A | 0.0504 (14) | 0.0488 (15) | 0.0326 (11) | 0.0040 (11) | 0.0190 (10) | 0.0026 (10) |
C5A | 0.0615 (16) | 0.0470 (14) | 0.0292 (11) | 0.0103 (12) | 0.0183 (11) | −0.0032 (10) |
C6A | 0.0444 (12) | 0.0346 (11) | 0.0244 (10) | 0.0040 (9) | 0.0048 (8) | −0.0009 (8) |
C7A | 0.0391 (11) | 0.0305 (11) | 0.0277 (10) | 0.0006 (9) | 0.0004 (8) | −0.0011 (9) |
C8A | 0.0489 (13) | 0.0254 (10) | 0.0389 (12) | −0.0036 (9) | 0.0012 (10) | 0.0002 (9) |
C9A | 0.0397 (11) | 0.0346 (11) | 0.0348 (11) | −0.0061 (9) | 0.0046 (9) | 0.0067 (9) |
C10A | 0.0294 (10) | 0.0354 (11) | 0.0267 (10) | −0.0009 (8) | 0.0042 (8) | 0.0022 (8) |
C11A | 0.0336 (10) | 0.0284 (10) | 0.0272 (9) | 0.0005 (8) | 0.0063 (8) | 0.0011 (8) |
C12A | 0.0335 (10) | 0.0290 (10) | 0.0259 (9) | 0.0001 (8) | 0.0034 (8) | 0.0013 (8) |
C13A | 0.0302 (10) | 0.0470 (13) | 0.0249 (10) | −0.0029 (9) | 0.0047 (8) | 0.0033 (9) |
C14A | 0.0598 (16) | 0.0396 (13) | 0.0468 (14) | 0.0033 (12) | 0.0009 (12) | 0.0101 (11) |
N1A | 0.0565 (12) | 0.0300 (10) | 0.0299 (10) | 0.0033 (9) | 0.0073 (8) | −0.0051 (8) |
N2A | 0.0484 (11) | 0.0406 (11) | 0.0242 (9) | −0.0095 (9) | 0.0042 (8) | 0.0059 (8) |
N3A | 0.0584 (14) | 0.0480 (13) | 0.0369 (11) | −0.0100 (11) | 0.0220 (10) | −0.0040 (10) |
O1A | 0.0491 (10) | 0.0564 (11) | 0.0326 (9) | −0.0177 (9) | 0.0130 (7) | −0.0013 (8) |
C1B | 0.0378 (11) | 0.0373 (11) | 0.0246 (9) | 0.0035 (9) | 0.0055 (8) | 0.0031 (8) |
C2B | 0.0446 (12) | 0.0374 (12) | 0.0286 (10) | 0.0001 (10) | 0.0056 (9) | 0.0011 (9) |
C3B | 0.0306 (10) | 0.0397 (12) | 0.0316 (11) | −0.0035 (9) | 0.0048 (8) | 0.0042 (9) |
C4B | 0.0374 (12) | 0.0546 (15) | 0.0405 (13) | 0.0065 (11) | 0.0144 (10) | 0.0068 (11) |
C5B | 0.0567 (15) | 0.0468 (14) | 0.0300 (11) | 0.0110 (12) | 0.0161 (10) | −0.0004 (10) |
C6B | 0.0424 (12) | 0.0370 (12) | 0.0290 (10) | 0.0084 (10) | 0.0078 (9) | −0.0006 (9) |
C7B | 0.0423 (12) | 0.0334 (11) | 0.0303 (11) | 0.0067 (9) | 0.0045 (9) | −0.0026 (9) |
C8B | 0.0524 (14) | 0.0302 (11) | 0.0402 (12) | 0.0009 (10) | 0.0088 (10) | −0.0018 (10) |
C9B | 0.0440 (12) | 0.0355 (12) | 0.0365 (11) | −0.0002 (10) | 0.0108 (10) | 0.0052 (10) |
C10B | 0.0341 (10) | 0.0360 (11) | 0.0265 (10) | 0.0030 (9) | 0.0056 (8) | 0.0018 (8) |
C11B | 0.0378 (11) | 0.0305 (10) | 0.0267 (10) | 0.0021 (9) | 0.0054 (8) | −0.0017 (8) |
C12B | 0.0346 (10) | 0.0319 (11) | 0.0269 (10) | 0.0045 (8) | 0.0037 (8) | 0.0016 (8) |
C13B | 0.0340 (10) | 0.0422 (13) | 0.0290 (10) | 0.0003 (9) | 0.0081 (8) | 0.0023 (9) |
C14B | 0.0510 (15) | 0.0509 (16) | 0.0601 (17) | 0.0110 (13) | 0.0074 (13) | 0.0052 (14) |
N1B | 0.0594 (13) | 0.0338 (10) | 0.0301 (10) | 0.0071 (9) | 0.0130 (9) | −0.0050 (8) |
N2B | 0.0328 (9) | 0.0389 (10) | 0.0335 (10) | −0.0025 (8) | 0.0057 (8) | 0.0045 (8) |
N3B | 0.0698 (15) | 0.0424 (12) | 0.0336 (11) | 0.0032 (11) | 0.0220 (10) | −0.0002 (10) |
O1B | 0.0598 (11) | 0.0434 (10) | 0.0372 (9) | 0.0017 (9) | 0.0198 (8) | 0.0061 (8) |
C15 | 0.0391 (11) | 0.0325 (11) | 0.0346 (11) | −0.0057 (9) | 0.0043 (9) | 0.0064 (9) |
C16 | 0.0469 (13) | 0.0672 (18) | 0.0336 (12) | −0.0073 (13) | −0.0001 (10) | 0.0125 (12) |
C17 | 0.0465 (14) | 0.084 (2) | 0.0275 (11) | −0.0108 (14) | 0.0035 (10) | 0.0141 (12) |
C18 | 0.0516 (13) | 0.0390 (12) | 0.0236 (10) | 0.0035 (10) | 0.0067 (9) | 0.0017 (9) |
O2 | 0.0551 (12) | 0.0796 (16) | 0.0574 (13) | 0.0200 (11) | 0.0100 (10) | 0.0230 (12) |
O3 | 0.0499 (10) | 0.0665 (13) | 0.0393 (9) | −0.0131 (9) | 0.0132 (8) | −0.0027 (9) |
O4 | 0.0563 (11) | 0.0581 (12) | 0.0337 (9) | 0.0077 (9) | −0.0020 (8) | 0.0015 (8) |
O5 | 0.0714 (14) | 0.107 (2) | 0.0336 (10) | −0.0011 (14) | 0.0171 (9) | 0.0193 (12) |
O1W | 0.0471 (11) | 0.0607 (13) | 0.0470 (11) | 0.0123 (10) | 0.0051 (9) | 0.0073 (10) |
O2W | 0.0476 (13) | 0.159 (3) | 0.0417 (12) | −0.0034 (16) | 0.0062 (10) | 0.0293 (15) |
O3W | 0.112 (2) | 0.0581 (15) | 0.0516 (13) | −0.0239 (15) | −0.0258 (14) | 0.0098 (11) |
Geometric parameters (Å, º) top
C1A—C6A | 1.363 (3) | C4B—C5B | 1.527 (4) |
C1A—C12A | 1.441 (3) | C4B—H4C | 0.9700 |
C1A—C2A | 1.500 (3) | C4B—H4D | 0.9700 |
C2A—C3A | 1.530 (3) | C5B—C6B | 1.492 (3) |
C2A—H2A | 0.9700 | C5B—H5C | 0.9700 |
C2A—H2B | 0.9700 | C5B—H5D | 0.9700 |
C3A—N2A | 1.500 (3) | C6B—N1B | 1.375 (3) |
C3A—C4A | 1.522 (3) | C7B—N1B | 1.376 (3) |
C3A—H3A | 0.9800 | C7B—C8B | 1.398 (3) |
C4A—C5A | 1.529 (4) | C7B—C12B | 1.416 (3) |
C4A—H4A | 0.9700 | C8B—C9B | 1.383 (4) |
C4A—H4B | 0.9700 | C8B—H8B | 0.9300 |
C5A—C6A | 1.502 (3) | C9B—C10B | 1.406 (3) |
C5A—H5A | 0.9700 | C9B—H9B | 0.9300 |
C5A—H5B | 0.9700 | C10B—C11B | 1.393 (3) |
C6A—N1A | 1.371 (3) | C10B—C13B | 1.496 (3) |
C7A—N1A | 1.371 (3) | C11B—C12B | 1.398 (3) |
C7A—C8A | 1.397 (3) | C11B—H11B | 0.9300 |
C7A—C12A | 1.421 (3) | C13B—O1B | 1.248 (3) |
C8A—C9A | 1.379 (3) | C13B—N3B | 1.330 (3) |
C8A—H8A | 0.9300 | C14B—N2B | 1.485 (4) |
C9A—C10A | 1.405 (3) | C14B—H14D | 0.9600 |
C9A—H9A | 0.9300 | C14B—H14E | 0.9600 |
C10A—C11A | 1.390 (3) | C14B—H14F | 0.9600 |
C10A—C13A | 1.494 (3) | N1B—H6N | 0.81 (4) |
C11A—C12A | 1.400 (3) | N2B—H7N | 0.90 (3) |
C11A—H11A | 0.9300 | N2B—H8N | 0.86 (3) |
C13A—O1A | 1.250 (3) | N3B—H9N | 0.85 (4) |
C13A—N3A | 1.328 (3) | N3B—H10N | 0.89 (3) |
C14A—N2A | 1.485 (4) | C15—O2 | 1.232 (3) |
C14A—H14A | 0.9600 | C15—O3 | 1.254 (3) |
C14A—H14B | 0.9600 | C15—C16 | 1.514 (3) |
C14A—H14C | 0.9600 | C16—C17 | 1.491 (4) |
N1A—H1N | 0.84 (4) | C16—H16A | 0.9700 |
N2A—H2N | 0.85 (3) | C16—H16B | 0.9700 |
N2A—H3N | 0.87 (3) | C17—C18 | 1.527 (3) |
N3A—H4N | 0.89 (3) | C17—H17A | 0.9700 |
N3A—H5N | 0.81 (4) | C17—H17B | 0.9700 |
C1B—C6B | 1.364 (3) | C18—O4 | 1.246 (3) |
C1B—C12B | 1.435 (3) | C18—O5 | 1.246 (3) |
C1B—C2B | 1.491 (3) | O1W—H1W | 0.81 (4) |
C2B—C3B | 1.537 (3) | O1W—H2W | 0.83 (4) |
C2B—H2C | 0.9700 | O2W—H3W | 0.82 (6) |
C2B—H2D | 0.9700 | O2W—H4W | 0.84 (4) |
C3B—N2B | 1.504 (3) | O3W—H5W | 0.82 (4) |
C3B—C4B | 1.524 (4) | O3W—H6W | 0.89 (5) |
C3B—H3B | 0.9800 | | |
| | | |
C6A—C1A—C12A | 106.8 (2) | C4B—C3B—C2B | 112.3 (2) |
C6A—C1A—C2A | 122.4 (2) | N2B—C3B—H3B | 108.0 |
C12A—C1A—C2A | 130.7 (2) | C4B—C3B—H3B | 108.0 |
C1A—C2A—C3A | 107.08 (18) | C2B—C3B—H3B | 108.0 |
C1A—C2A—H2A | 110.3 | C3B—C4B—C5B | 114.9 (2) |
C3A—C2A—H2A | 110.3 | C3B—C4B—H4C | 108.5 |
C1A—C2A—H2B | 110.3 | C5B—C4B—H4C | 108.5 |
C3A—C2A—H2B | 110.3 | C3B—C4B—H4D | 108.5 |
H2A—C2A—H2B | 108.6 | C5B—C4B—H4D | 108.5 |
N2A—C3A—C4A | 110.51 (19) | H4C—C4B—H4D | 107.5 |
N2A—C3A—C2A | 112.09 (19) | C6B—C5B—C4B | 109.5 (2) |
C4A—C3A—C2A | 110.4 (2) | C6B—C5B—H5C | 109.8 |
N2A—C3A—H3A | 107.9 | C4B—C5B—H5C | 109.8 |
C4A—C3A—H3A | 107.9 | C6B—C5B—H5D | 109.8 |
C2A—C3A—H3A | 107.9 | C4B—C5B—H5D | 109.8 |
C3A—C4A—C5A | 109.6 (2) | H5C—C5B—H5D | 108.2 |
C3A—C4A—H4A | 109.7 | C1B—C6B—N1B | 110.2 (2) |
C5A—C4A—H4A | 109.7 | C1B—C6B—C5B | 124.8 (2) |
C3A—C4A—H4B | 109.7 | N1B—C6B—C5B | 125.0 (2) |
C5A—C4A—H4B | 109.7 | N1B—C7B—C8B | 131.3 (2) |
H4A—C4A—H4B | 108.2 | N1B—C7B—C12B | 107.5 (2) |
C6A—C5A—C4A | 109.4 (2) | C8B—C7B—C12B | 121.2 (2) |
C6A—C5A—H5A | 109.8 | C9B—C8B—C7B | 117.6 (2) |
C4A—C5A—H5A | 109.8 | C9B—C8B—H8B | 121.2 |
C6A—C5A—H5B | 109.8 | C7B—C8B—H8B | 121.2 |
C4A—C5A—H5B | 109.8 | C8B—C9B—C10B | 121.9 (2) |
H5A—C5A—H5B | 108.2 | C8B—C9B—H9B | 119.0 |
C1A—C6A—N1A | 110.3 (2) | C10B—C9B—H9B | 119.0 |
C1A—C6A—C5A | 125.7 (2) | C11B—C10B—C9B | 120.5 (2) |
N1A—C6A—C5A | 123.9 (2) | C11B—C10B—C13B | 121.2 (2) |
N1A—C7A—C8A | 130.3 (2) | C9B—C10B—C13B | 118.3 (2) |
N1A—C7A—C12A | 107.9 (2) | C10B—C11B—C12B | 118.5 (2) |
C8A—C7A—C12A | 121.8 (2) | C10B—C11B—H11B | 120.7 |
C9A—C8A—C7A | 117.6 (2) | C12B—C11B—H11B | 120.7 |
C9A—C8A—H8A | 121.2 | C11B—C12B—C7B | 120.2 (2) |
C7A—C8A—H8A | 121.2 | C11B—C12B—C1B | 132.9 (2) |
C8A—C9A—C10A | 121.9 (2) | C7B—C12B—C1B | 106.9 (2) |
C8A—C9A—H9A | 119.0 | O1B—C13B—N3B | 121.0 (2) |
C10A—C9A—H9A | 119.0 | O1B—C13B—C10B | 120.8 (2) |
C11A—C10A—C9A | 120.4 (2) | N3B—C13B—C10B | 118.2 (2) |
C11A—C10A—C13A | 122.4 (2) | N2B—C14B—H14D | 109.5 |
C9A—C10A—C13A | 117.3 (2) | N2B—C14B—H14E | 109.5 |
C10A—C11A—C12A | 119.3 (2) | H14D—C14B—H14E | 109.5 |
C10A—C11A—H11A | 120.4 | N2B—C14B—H14F | 109.5 |
C12A—C11A—H11A | 120.4 | H14D—C14B—H14F | 109.5 |
C11A—C12A—C7A | 119.0 (2) | H14E—C14B—H14F | 109.5 |
C11A—C12A—C1A | 134.8 (2) | C6B—N1B—C7B | 108.8 (2) |
C7A—C12A—C1A | 106.13 (19) | C6B—N1B—H6N | 126 (3) |
O1A—C13A—N3A | 120.0 (2) | C7B—N1B—H6N | 125 (3) |
O1A—C13A—C10A | 120.1 (2) | C14B—N2B—C3B | 113.3 (2) |
N3A—C13A—C10A | 119.8 (2) | C14B—N2B—H7N | 105 (2) |
N2A—C14A—H14A | 109.5 | C3B—N2B—H7N | 112 (2) |
N2A—C14A—H14B | 109.5 | C14B—N2B—H8N | 108.8 (17) |
H14A—C14A—H14B | 109.5 | C3B—N2B—H8N | 111.3 (18) |
N2A—C14A—H14C | 109.5 | H7N—N2B—H8N | 105 (3) |
H14A—C14A—H14C | 109.5 | C13B—N3B—H9N | 125 (3) |
H14B—C14A—H14C | 109.5 | C13B—N3B—H10N | 117 (2) |
C6A—N1A—C7A | 108.85 (19) | H9N—N3B—H10N | 118 (3) |
C6A—N1A—H1N | 122 (2) | O2—C15—O3 | 121.9 (2) |
C7A—N1A—H1N | 129 (2) | O2—C15—C16 | 119.7 (2) |
C14A—N2A—C3A | 113.3 (2) | O3—C15—C16 | 118.3 (2) |
C14A—N2A—H2N | 109 (2) | C17—C16—C15 | 114.8 (2) |
C3A—N2A—H2N | 109 (2) | C17—C16—H16A | 108.6 |
C14A—N2A—H3N | 108 (2) | C15—C16—H16A | 108.6 |
C3A—N2A—H3N | 108 (2) | C17—C16—H16B | 108.6 |
H2N—N2A—H3N | 110 (3) | C15—C16—H16B | 108.6 |
C13A—N3A—H4N | 119 (2) | H16A—C16—H16B | 107.5 |
C13A—N3A—H5N | 119 (3) | C16—C17—C18 | 116.1 (2) |
H4N—N3A—H5N | 122 (4) | C16—C17—H17A | 108.2 |
C6B—C1B—C12B | 106.7 (2) | C18—C17—H17A | 108.2 |
C6B—C1B—C2B | 124.5 (2) | C16—C17—H17B | 108.2 |
C12B—C1B—C2B | 128.8 (2) | C18—C17—H17B | 108.2 |
C1B—C2B—C3B | 110.97 (19) | H17A—C17—H17B | 107.4 |
C1B—C2B—H2C | 109.4 | O4—C18—O5 | 126.1 (2) |
C3B—C2B—H2C | 109.4 | O4—C18—C17 | 117.9 (2) |
C1B—C2B—H2D | 109.4 | O5—C18—C17 | 116.0 (2) |
C3B—C2B—H2D | 109.4 | H1W—O1W—H2W | 100 (4) |
H2C—C2B—H2D | 108.0 | H3W—O2W—H4W | 117 (4) |
N2B—C3B—C4B | 110.7 (2) | H5W—O3W—H6W | 101 (4) |
N2B—C3B—C2B | 109.73 (18) | | |
| | | |
C6A—C1A—C2A—C3A | −20.8 (3) | C1B—C2B—C3B—C4B | −40.5 (3) |
C12A—C1A—C2A—C3A | 155.0 (2) | N2B—C3B—C4B—C5B | −66.0 (3) |
C1A—C2A—C3A—N2A | 179.06 (19) | C2B—C3B—C4B—C5B | 57.0 (3) |
C1A—C2A—C3A—C4A | 55.4 (3) | C3B—C4B—C5B—C6B | −42.7 (3) |
N2A—C3A—C4A—C5A | 166.0 (2) | C12B—C1B—C6B—N1B | 0.4 (3) |
C2A—C3A—C4A—C5A | −69.4 (3) | C2B—C1B—C6B—N1B | 177.2 (2) |
C3A—C4A—C5A—C6A | 42.2 (3) | C12B—C1B—C6B—C5B | 178.5 (2) |
C12A—C1A—C6A—N1A | −1.3 (3) | C2B—C1B—C6B—C5B | −4.6 (4) |
C2A—C1A—C6A—N1A | 175.4 (2) | C4B—C5B—C6B—C1B | 17.0 (3) |
C12A—C1A—C6A—C5A | −179.0 (2) | C4B—C5B—C6B—N1B | −165.1 (2) |
C2A—C1A—C6A—C5A | −2.4 (4) | N1B—C7B—C8B—C9B | −179.8 (2) |
C4A—C5A—C6A—C1A | −8.5 (4) | C12B—C7B—C8B—C9B | 0.3 (4) |
C4A—C5A—C6A—N1A | 174.0 (2) | C7B—C8B—C9B—C10B | 0.8 (4) |
N1A—C7A—C8A—C9A | −178.1 (2) | C8B—C9B—C10B—C11B | −0.9 (4) |
C12A—C7A—C8A—C9A | 0.8 (4) | C8B—C9B—C10B—C13B | −179.2 (2) |
C7A—C8A—C9A—C10A | 0.5 (4) | C9B—C10B—C11B—C12B | −0.1 (3) |
C8A—C9A—C10A—C11A | −1.5 (3) | C13B—C10B—C11B—C12B | 178.2 (2) |
C8A—C9A—C10A—C13A | 177.7 (2) | C10B—C11B—C12B—C7B | 1.1 (3) |
C9A—C10A—C11A—C12A | 1.3 (3) | C10B—C11B—C12B—C1B | −179.4 (2) |
C13A—C10A—C11A—C12A | −177.9 (2) | N1B—C7B—C12B—C11B | 178.8 (2) |
C10A—C11A—C12A—C7A | −0.1 (3) | C8B—C7B—C12B—C11B | −1.2 (4) |
C10A—C11A—C12A—C1A | 179.9 (2) | N1B—C7B—C12B—C1B | −0.8 (3) |
N1A—C7A—C12A—C11A | 178.10 (19) | C8B—C7B—C12B—C1B | 179.1 (2) |
C8A—C7A—C12A—C11A | −1.0 (3) | C6B—C1B—C12B—C11B | −179.3 (2) |
N1A—C7A—C12A—C1A | −1.9 (3) | C2B—C1B—C12B—C11B | 4.0 (4) |
C8A—C7A—C12A—C1A | 179.0 (2) | C6B—C1B—C12B—C7B | 0.3 (3) |
C6A—C1A—C12A—C11A | −178.1 (2) | C2B—C1B—C12B—C7B | −176.4 (2) |
C2A—C1A—C12A—C11A | 5.7 (5) | C11B—C10B—C13B—O1B | −160.4 (2) |
C6A—C1A—C12A—C7A | 1.9 (3) | C9B—C10B—C13B—O1B | 17.9 (3) |
C2A—C1A—C12A—C7A | −174.4 (2) | C11B—C10B—C13B—N3B | 19.8 (3) |
C11A—C10A—C13A—O1A | −166.2 (2) | C9B—C10B—C13B—N3B | −161.9 (2) |
C9A—C10A—C13A—O1A | 14.6 (3) | C1B—C6B—N1B—C7B | −0.9 (3) |
C11A—C10A—C13A—N3A | 15.5 (3) | C5B—C6B—N1B—C7B | −179.0 (2) |
C9A—C10A—C13A—N3A | −163.7 (2) | C8B—C7B—N1B—C6B | −178.9 (3) |
C1A—C6A—N1A—C7A | 0.1 (3) | C12B—C7B—N1B—C6B | 1.0 (3) |
C5A—C6A—N1A—C7A | 177.9 (2) | C4B—C3B—N2B—C14B | −160.4 (2) |
C8A—C7A—N1A—C6A | −179.9 (2) | C2B—C3B—N2B—C14B | 75.1 (3) |
C12A—C7A—N1A—C6A | 1.1 (3) | O2—C15—C16—C17 | −48.0 (4) |
C4A—C3A—N2A—C14A | −160.9 (2) | O3—C15—C16—C17 | 133.8 (3) |
C2A—C3A—N2A—C14A | 75.5 (3) | C15—C16—C17—C18 | 177.5 (3) |
C6B—C1B—C2B—C3B | 16.1 (3) | C16—C17—C18—O4 | 19.2 (4) |
C12B—C1B—C2B—C3B | −167.7 (2) | C16—C17—C18—O5 | −162.2 (3) |
C1B—C2B—C3B—N2B | 83.1 (2) | | |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N1A—H1N···O2i | 0.84 (4) | 2.20 (4) | 2.976 (3) | 154 (3) |
N1A—H1N···O3i | 0.84 (4) | 2.40 (4) | 3.140 (3) | 147 (3) |
N2A—H2N···O3 | 0.85 (3) | 2.00 (3) | 2.826 (3) | 162 (3) |
N2A—H3N···O5ii | 0.87 (3) | 1.93 (3) | 2.738 (3) | 154 (3) |
N3A—H4N···O1B | 0.89 (3) | 2.06 (4) | 2.951 (3) | 173 (3) |
N3A—H5N···O5 | 0.81 (4) | 2.60 (4) | 3.277 (4) | 142 (3) |
N1B—H6N···O4iii | 0.81 (4) | 2.23 (4) | 2.981 (3) | 153 (3) |
N2B—H7N···O2Wiv | 0.90 (3) | 1.80 (4) | 2.687 (3) | 168 (3) |
N2B—H8N···O1Aiv | 0.86 (3) | 1.96 (3) | 2.792 (3) | 163 (2) |
N3B—H9N···O1W | 0.85 (4) | 2.36 (4) | 3.175 (3) | 160 (3) |
N3B—H10N···O1A | 0.89 (3) | 2.05 (3) | 2.930 (3) | 169 (3) |
O1W—H1W···O3v | 0.81 (4) | 1.94 (4) | 2.735 (3) | 172 (4) |
O1W—H2W···O3W | 0.83 (4) | 2.01 (4) | 2.826 (3) | 167 (3) |
O2W—H3W···O1W | 0.82 (6) | 1.91 (6) | 2.729 (3) | 177 (5) |
O2W—H4W···O2vi | 0.84 (4) | 1.82 (4) | 2.661 (4) | 179 (4) |
O3W—H5W···O4vii | 0.82 (4) | 1.95 (4) | 2.749 (3) | 165 (4) |
O3W—H6W···O1Bviii | 0.89 (5) | 1.97 (5) | 2.846 (3) | 168 (4) |
C3A—H3A···O1Bii | 0.98 | 2.54 | 3.462 (3) | 156 |
Symmetry codes: (i) −x−1, y+1/2, −z+4; (ii) x, y, z+1; (iii) x+1, y, z−1; (iv) x, y, z−1; (v) −x−1, y+1/2, −z+3; (vi) −x, y+1/2, −z+3; (vii) −x−1, y+1/2, −z+2; (viii) −x, y+1/2, −z+2. |
Table 1. Selected geometric parameters (Å ,° ) for (I)–(III) topParameter | (I) | (IIA) cation/anion | (IIB) cation/anion | (III) |
C15—O2 | 1.244 (2) | 1.302 (5) | 1.302 (6) | 1.232 (3) |
C15—O3 | 1.257 (2) | 1.183 (5) | 1.172 (5) | 1.254 (3) |
C18—O4 | | 1.225 (5) | 1.226 (5) | 1.246 (3) |
C18—O5 | | 1.268 (5) | 1.264 (5) | 1.246 (3) |
C13—O1 | 1.234 (2) | 1.253 (4) | 1.250 (4) | 1.250 (3)/1.248 (3)* |
C13—N3 | 1.325 (3) | 1.314 (5) | 1.320 (5) | 1.328 (3)/1.330 (3)* |
| | | | |
O2—C15—C16 | 118.8 (2) | 113.2 (3) | 114.0 (4) | 119.7 (2) |
O3—C15—C16 | 117.8 (2) | 124.0 (4) | 124.1 (4) | 118.3 (2) |
O4—C18—C17 | | 119.6 (4) | 119.7 (4) | 117.9 (2) |
O5—C18—C17 | | 116.4 (3) | 116.5 (4) | 116.0 (2) |
O1—C13—N3 | 120.42 (19) | 120.2 (3) | 120.6 (3) | 120.0 (2)/121.0 (2)* |
Note: (*) data for cations A and B, respectively, of
frovatriptan in (III). |
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