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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-1H-carbazol-3-aminium acetate, C14H18N3O+·C2H3O2, (I), (R)-(+)-6-carbamoyl-N-methyl-2,3,4,9-tetra­hydro-1H-carbazol-3-aminium 3-carb­oxy­propano­ate monohydrate, C14H18N3O+·C4H5O4·H2O, (II), and bis­[(R)-(+)-6-carbamoyl-N-methyl-2,3,4,9-tetra­hydro-1H-carbazol-3-aminium] succinate trihydrate, 2C14H18N3O+·C4H4O42−·3H2O, (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

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270113005878/cu3026sup1.cif
Contains datablocks I, II, III, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108270113005878/cu3026Isup2.hkl
Contains datablock I

cml

Chemical Markup Language (CML) file https://doi.org/10.1107/S0108270113005878/cu3026Isup5.cml
Supplementary material

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108270113005878/cu3026IIsup3.hkl
Contains datablock II

cml

Chemical Markup Language (CML) file https://doi.org/10.1107/S0108270113005878/cu3026IIsup6.cml
Supplementary material

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108270113005878/cu3026IIIsup4.hkl
Contains datablock III

cml

Chemical Markup Language (CML) file https://doi.org/10.1107/S0108270113005878/cu3026IIIsup7.cml
Supplementary material

CCDC references: 934621; 934622; 934623

Computing details top

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-1H-carbazol-3-aminium acetate top
Crystal data top
C14H18N3O+·C2H3O2F(000) = 648
Mr = 303.36Dx = 1.247 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 2571 reflections
a = 11.2397 (8) Åθ = 2.2–22.0°
b = 16.7124 (13) ŵ = 0.09 mm1
c = 8.6528 (6) ÅT = 294 K
β = 96.150 (1)°Block, colorless
V = 1616.0 (2) Å30.17 × 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 tubeRint = 0.045
Graphite monochromatorθmax = 25.0°, θmin = 1.8°
ω scanh = 1313
15459 measured reflectionsk = 1919
2855 independent reflectionsl = 1010
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.050Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.120H 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 parametersΔρmax = 0.19 e Å3
0 restraintsΔρmin = 0.13 e Å3
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
xyzUiso*/Ueq
C10.15669 (17)0.06969 (12)0.6091 (2)0.0368 (5)
C20.17256 (18)0.03688 (14)0.7713 (2)0.0449 (6)
H2A0.10310.00530.79000.054*
H2B0.18000.08060.84550.054*
C30.28480 (18)0.01529 (13)0.7927 (2)0.0416 (5)
H30.26560.06680.74200.050*
C40.39019 (19)0.02022 (14)0.7218 (2)0.0459 (6)
H4A0.45920.01440.74390.055*
H4B0.40970.07190.76890.055*
C50.36346 (18)0.03042 (14)0.5460 (2)0.0432 (5)
H5A0.42350.06450.50710.052*
H5B0.36550.02120.49510.052*
C60.24322 (17)0.06705 (12)0.5115 (2)0.0378 (5)
C70.09019 (18)0.13105 (13)0.3805 (2)0.0382 (5)
C80.01499 (19)0.17453 (14)0.2741 (2)0.0484 (6)
H80.03900.18960.17870.058*
C90.09617 (19)0.19463 (14)0.3142 (2)0.0445 (6)
H90.14730.22440.24490.053*
C100.13513 (17)0.17166 (12)0.4565 (2)0.0343 (5)
C110.05850 (17)0.12963 (12)0.5627 (2)0.0362 (5)
H110.08340.11470.65760.043*
C120.05580 (17)0.10965 (12)0.5279 (2)0.0351 (5)
C130.25671 (17)0.19209 (12)0.5001 (2)0.0337 (5)
C140.2281 (2)0.06681 (16)1.0492 (3)0.0580 (7)
H14A0.16550.02841.05710.087*
H14B0.26250.08171.15150.087*
H14C0.19560.11340.99510.087*
N10.20370 (15)0.10322 (11)0.3724 (2)0.0427 (5)
H1N0.2483 (19)0.1081 (12)0.293 (3)0.044 (6)*
N20.32219 (17)0.03103 (13)0.9622 (2)0.0425 (5)
H2N0.388 (2)0.0659 (14)0.972 (2)0.051 (6)*
H3N0.347 (2)0.0198 (17)1.016 (3)0.071 (8)*
N30.32981 (18)0.23459 (13)0.4017 (2)0.0500 (5)
H4N0.310 (2)0.2531 (14)0.316 (3)0.049 (7)*
H5N0.395 (2)0.2532 (15)0.437 (3)0.060 (7)*
O10.28853 (12)0.17014 (9)0.62550 (16)0.0453 (4)
C150.58316 (19)0.16208 (13)0.9070 (2)0.0398 (5)
C160.6166 (3)0.24560 (16)0.8658 (4)0.0777 (9)
H16A0.68390.26300.93540.116*
H16B0.63730.24660.76100.116*
H16C0.55010.28070.87460.116*
O20.49328 (13)0.15188 (9)0.97702 (18)0.0503 (4)
O30.64897 (14)0.10589 (9)0.87036 (18)0.0526 (4)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0336 (11)0.0425 (12)0.0348 (11)0.0049 (9)0.0054 (9)0.0032 (9)
C20.0377 (12)0.0576 (15)0.0405 (12)0.0085 (10)0.0084 (10)0.0086 (10)
C30.0398 (12)0.0477 (13)0.0367 (12)0.0052 (10)0.0008 (9)0.0025 (10)
C40.0353 (12)0.0541 (14)0.0483 (13)0.0096 (10)0.0044 (10)0.0025 (11)
C50.0376 (12)0.0481 (13)0.0455 (13)0.0080 (10)0.0116 (10)0.0024 (10)
C60.0343 (11)0.0425 (12)0.0371 (11)0.0033 (10)0.0061 (9)0.0016 (9)
C70.0333 (11)0.0479 (13)0.0342 (11)0.0044 (9)0.0079 (9)0.0020 (9)
C80.0438 (13)0.0685 (16)0.0347 (12)0.0065 (11)0.0123 (10)0.0135 (11)
C90.0375 (12)0.0594 (15)0.0369 (11)0.0110 (11)0.0056 (9)0.0112 (10)
C100.0322 (11)0.0385 (12)0.0324 (10)0.0012 (9)0.0033 (8)0.0015 (9)
C110.0369 (11)0.0415 (12)0.0314 (11)0.0001 (9)0.0087 (9)0.0001 (9)
C120.0319 (11)0.0401 (12)0.0337 (11)0.0025 (9)0.0053 (9)0.0003 (9)
C130.0339 (11)0.0363 (11)0.0312 (11)0.0004 (9)0.0043 (9)0.0037 (9)
C140.0617 (16)0.0637 (16)0.0498 (14)0.0020 (13)0.0107 (12)0.0176 (12)
N10.0350 (10)0.0599 (12)0.0353 (10)0.0086 (8)0.0138 (8)0.0069 (9)
N20.0413 (11)0.0449 (12)0.0409 (11)0.0098 (10)0.0021 (8)0.0059 (9)
N30.0412 (12)0.0674 (14)0.0439 (12)0.0188 (10)0.0155 (10)0.0128 (10)
O10.0392 (8)0.0606 (10)0.0376 (8)0.0057 (7)0.0114 (6)0.0049 (7)
C150.0397 (12)0.0428 (13)0.0376 (11)0.0035 (10)0.0066 (10)0.0027 (10)
C160.088 (2)0.0523 (16)0.097 (2)0.0116 (15)0.0285 (17)0.0032 (15)
O20.0453 (9)0.0471 (9)0.0618 (10)0.0023 (7)0.0207 (8)0.0062 (8)
O30.0549 (10)0.0512 (10)0.0560 (10)0.0063 (8)0.0254 (8)0.0019 (8)
Geometric parameters (Å, º) top
C1—C61.355 (3)C9—H90.9300
C1—C121.433 (3)C10—C111.382 (3)
C1—C21.499 (3)C10—C131.496 (3)
C2—C31.528 (3)C11—C121.391 (3)
C2—H2A0.9700C11—H110.9300
C2—H2B0.9700C13—O11.234 (2)
C3—N21.505 (3)C13—N31.325 (3)
C3—C41.512 (3)C14—N21.488 (3)
C3—H30.9800C14—H14A0.9600
C4—C51.529 (3)C14—H14B0.9600
C4—H4A0.9700C14—H14C0.9600
C4—H4B0.9700N1—H1N0.90 (2)
C5—C61.484 (3)N2—H2N0.94 (2)
C5—H5A0.9700N2—H3N0.99 (3)
C5—H5B0.9700N3—H4N0.86 (2)
C6—N11.378 (3)N3—H5N0.88 (3)
C7—N11.367 (3)C15—O21.244 (2)
C7—C81.387 (3)C15—O31.257 (2)
C7—C121.418 (3)C15—C161.499 (3)
C8—C91.374 (3)C16—H16A0.9600
C8—H80.9300C16—H16B0.9600
C9—C101.403 (3)C16—H16C0.9600
C6—C1—C12107.02 (17)C11—C10—C9119.42 (18)
C6—C1—C2123.35 (18)C11—C10—C13118.00 (17)
C12—C1—C2129.62 (17)C9—C10—C13122.57 (18)
C1—C2—C3109.63 (16)C10—C11—C12120.17 (18)
C1—C2—H2A109.7C10—C11—H11119.9
C3—C2—H2A109.7C12—C11—H11119.9
C1—C2—H2B109.7C11—C12—C7118.75 (18)
C3—C2—H2B109.7C11—C12—C1134.93 (18)
H2A—C2—H2B108.2C7—C12—C1106.32 (16)
N2—C3—C4108.35 (17)O1—C13—N3120.42 (19)
N2—C3—C2111.01 (16)O1—C13—C10120.85 (18)
C4—C3—C2113.52 (18)N3—C13—C10118.74 (18)
N2—C3—H3107.9N2—C14—H14A109.5
C4—C3—H3107.9N2—C14—H14B109.5
C2—C3—H3107.9H14A—C14—H14B109.5
C3—C4—C5111.63 (18)N2—C14—H14C109.5
C3—C4—H4A109.3H14A—C14—H14C109.5
C5—C4—H4A109.3H14B—C14—H14C109.5
C3—C4—H4B109.3C7—N1—C6108.67 (17)
C5—C4—H4B109.3C7—N1—H1N127.5 (14)
H4A—C4—H4B108.0C6—N1—H1N123.8 (13)
C6—C5—C4108.87 (16)C14—N2—C3115.08 (18)
C6—C5—H5A109.9C14—N2—H2N107.5 (13)
C4—C5—H5A109.9C3—N2—H2N109.6 (13)
C6—C5—H5B109.9C14—N2—H3N106.3 (14)
C4—C5—H5B109.9C3—N2—H3N110.0 (14)
H5A—C5—H5B108.3H2N—N2—H3N108 (2)
C1—C6—N1110.15 (18)C13—N3—H4N123.5 (15)
C1—C6—C5125.95 (18)C13—N3—H5N116.6 (16)
N1—C6—C5123.90 (17)H4N—N3—H5N118 (2)
N1—C7—C8130.57 (19)O2—C15—O3123.4 (2)
N1—C7—C12107.82 (17)O2—C15—C16118.8 (2)
C8—C7—C12121.60 (18)O3—C15—C16117.8 (2)
C9—C8—C7117.79 (19)C15—C16—H16A109.5
C9—C8—H8121.1C15—C16—H16B109.5
C7—C8—H8121.1H16A—C16—H16B109.5
C8—C9—C10122.19 (19)C15—C16—H16C109.5
C8—C9—H9118.9H16A—C16—H16C109.5
C10—C9—H9118.9H16B—C16—H16C109.5
C6—C1—C2—C313.2 (3)C10—C11—C12—C71.9 (3)
C12—C1—C2—C3168.2 (2)C10—C11—C12—C1178.0 (2)
C1—C2—C3—N2164.77 (18)N1—C7—C12—C11178.25 (19)
C1—C2—C3—C442.4 (3)C8—C7—C12—C113.2 (3)
N2—C3—C4—C5174.42 (18)N1—C7—C12—C11.8 (2)
C2—C3—C4—C561.8 (2)C8—C7—C12—C1176.8 (2)
C3—C4—C5—C645.9 (3)C6—C1—C12—C11178.9 (2)
C12—C1—C6—N10.1 (3)C2—C1—C12—C112.4 (4)
C2—C1—C6—N1178.69 (19)C6—C1—C12—C71.2 (2)
C12—C1—C6—C5179.5 (2)C2—C1—C12—C7177.6 (2)
C2—C1—C6—C51.7 (4)C11—C10—C13—O11.9 (3)
C4—C5—C6—C117.9 (3)C9—C10—C13—O1179.2 (2)
C4—C5—C6—N1162.5 (2)C11—C10—C13—N3177.85 (19)
N1—C7—C8—C9179.9 (2)C9—C10—C13—N31.1 (3)
C12—C7—C8—C91.7 (3)C8—C7—N1—C6176.7 (2)
C7—C8—C9—C100.9 (4)C12—C7—N1—C61.7 (2)
C8—C9—C10—C112.1 (3)C1—C6—N1—C71.0 (3)
C8—C9—C10—C13179.0 (2)C5—C6—N1—C7179.4 (2)
C9—C10—C11—C120.6 (3)C4—C3—N2—C14179.59 (19)
C13—C10—C11—C12179.59 (18)C2—C3—N2—C1455.1 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1N···O3i0.90 (2)1.92 (2)2.811 (2)173 (2)
N2—H2N···O20.94 (2)1.86 (2)2.782 (2)167 (2)
N2—H3N···O3ii0.99 (3)1.74 (3)2.709 (3)164 (2)
N3—H4N···O1iii0.86 (2)2.12 (3)2.950 (3)163 (2)
N3—H5N···O2iv0.88 (3)2.12 (3)2.914 (3)151 (2)
C9—H9···O1iii0.932.523.420 (3)163
C14—H14B···O1v0.962.423.310 (3)154
Symmetry codes: (i) x+1, y, z+1; (ii) x+1, y, z+2; (iii) x, y+1/2, z1/2; (iv) x, y+1/2, z+3/2; (v) x, y, z+2.
(II) (R)-(+)-6-Carbamoyl-N-methyl-2,3,4,9-tetrahydro-1H-carbazol-3-aminium 3-carboxypropanoate monohydrate top
Crystal data top
C14H18N3O+·C4H5O4·H2OF(000) = 808
Mr = 379.41Dx = 1.327 Mg m3
Monoclinic, P21Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ybCell parameters from 5616 reflections
a = 10.6206 (6) Åθ = 2.6–23.2°
b = 7.9939 (5) ŵ = 0.10 mm1
c = 22.3916 (13) ÅT = 294 K
β = 92.884 (1)°Needle, colorless
V = 1898.64 (19) Å30.18 × 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 tubeRint = 0.036
Graphite monochromatorθmax = 28.0°, θmin = 1.8°
ω scanh = 1313
22400 measured reflectionsk = 1010
4828 independent reflectionsl = 2928
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.066Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.157H 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 parametersΔρmax = 0.31 e Å3
7 restraintsΔρmin = 0.20 e Å3
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
xyzUiso*/Ueq
C1A0.8635 (3)0.0934 (5)0.22595 (14)0.0311 (7)
C2A0.8378 (3)0.1294 (5)0.16087 (15)0.0367 (8)
H2A0.87980.04770.13680.044*
H2B0.86870.23980.15120.044*
C3A0.6964 (3)0.1204 (5)0.14858 (14)0.0343 (7)
H3A0.66880.00540.15550.041*
C4A0.6274 (4)0.2366 (6)0.19005 (17)0.0444 (9)
H4A0.53840.23940.17790.053*
H4B0.66050.34920.18700.053*
C5A0.6438 (3)0.1762 (6)0.25518 (16)0.0450 (10)
H5A0.62780.26780.28220.054*
H5B0.58370.08780.26220.054*
C6A0.7750 (3)0.1124 (5)0.26704 (14)0.0340 (7)
C7A0.9414 (3)0.0073 (5)0.31718 (14)0.0328 (7)
C8A1.0265 (3)0.0580 (5)0.36097 (14)0.0350 (8)
H8A1.00460.07030.40040.042*
C9A1.1430 (3)0.1028 (5)0.34330 (15)0.0352 (8)
H9A1.20180.14390.37180.042*
C10A1.1774 (3)0.0891 (4)0.28353 (14)0.0322 (7)
C11A1.0919 (3)0.0259 (5)0.24016 (13)0.0304 (7)
H11A1.11380.01690.20060.036*
C12A0.9725 (3)0.0241 (4)0.25688 (13)0.0308 (7)
C13A1.3066 (3)0.1432 (5)0.26977 (15)0.0336 (7)
C14A0.5343 (5)0.1177 (11)0.0634 (2)0.088 (2)
H14A0.52470.00120.06700.132*
H14B0.52060.14960.02220.132*
H14C0.47400.17320.08700.132*
N1A0.8218 (3)0.0626 (4)0.32229 (13)0.0379 (7)
H1N0.786 (4)0.057 (7)0.353 (2)0.051 (13)*
N2A0.6626 (4)0.1661 (6)0.08462 (15)0.0493 (9)
H2N0.707 (4)0.112 (6)0.0641 (19)0.040 (12)*
H3N0.668 (5)0.279 (10)0.077 (2)0.080 (19)*
N3A1.3450 (3)0.1274 (5)0.21518 (15)0.0455 (9)
H4N1.291 (3)0.111 (5)0.1859 (17)0.033 (10)*
H5N1.411 (4)0.169 (5)0.2071 (16)0.030 (10)*
O1A1.3794 (2)0.2009 (4)0.31050 (11)0.0435 (7)
C1B2.1091 (3)0.5282 (5)0.28177 (14)0.0318 (7)
C2B2.1199 (3)0.5905 (5)0.34470 (16)0.0388 (8)
H2C2.07050.69190.34770.047*
H2D2.08540.50740.37090.047*
C3B2.2574 (3)0.6272 (5)0.36553 (16)0.0373 (8)
H3B2.25650.70650.39890.045*
C4B2.3316 (4)0.7059 (6)0.31623 (19)0.0462 (9)
H4C2.29590.81500.30680.055*
H4D2.41780.72290.33140.055*
C5B2.3333 (3)0.6036 (6)0.25862 (17)0.0438 (9)
H5C2.39290.51210.26380.053*
H5D2.35990.67380.22620.053*
C6B2.2046 (3)0.5361 (5)0.24360 (15)0.0358 (7)
C7B2.0412 (3)0.4282 (5)0.19026 (15)0.0366 (8)
C8B1.9594 (3)0.3612 (5)0.14621 (15)0.0407 (9)
H8B1.98590.34110.10790.049*
C9B1.8383 (3)0.3254 (5)0.16074 (16)0.0383 (8)
H9B1.78200.28120.13170.046*
C10B1.7975 (3)0.3544 (5)0.21903 (15)0.0347 (8)
C11B1.8798 (3)0.4203 (5)0.26287 (15)0.0331 (7)
H11B1.85330.43800.30130.040*
C12B2.0026 (3)0.4598 (5)0.24892 (14)0.0319 (7)
C13B1.6661 (3)0.3069 (5)0.23125 (15)0.0351 (7)
C14B2.4459 (4)0.4869 (8)0.4164 (2)0.0679 (15)
H14D2.44760.57990.44360.102*
H14E2.46880.38660.43790.102*
H14F2.50460.50640.38600.102*
N1B2.1634 (3)0.4755 (5)0.18869 (13)0.0414 (8)
H6N2.201 (3)0.470 (5)0.1611 (16)0.023 (9)*
N2B2.3170 (3)0.4684 (5)0.38836 (14)0.0396 (7)
H7N2.314 (4)0.386 (6)0.3552 (19)0.043 (11)*
H8N2.266 (4)0.431 (6)0.4148 (18)0.041 (11)*
N3B1.6348 (3)0.2953 (6)0.28742 (14)0.0476 (9)
H9N1.688 (4)0.305 (6)0.3166 (19)0.042 (11)*
H10N1.560 (3)0.261 (5)0.2944 (14)0.020 (8)*
O1B1.5863 (2)0.2804 (4)0.18935 (11)0.0489 (7)
C15A0.7918 (5)0.6803 (5)0.45505 (17)0.0467 (10)
C16A0.8210 (7)0.5154 (6)0.4830 (2)0.085 (2)
H16A0.90860.51550.49750.102*
H16B0.76990.50240.51740.102*
C17A0.7996 (5)0.3689 (6)0.44335 (19)0.0561 (12)
H17A0.86950.36060.41720.067*
H17B0.72380.38840.41830.067*
C18A0.7863 (4)0.2048 (5)0.47491 (16)0.0387 (8)
O2A0.8080 (5)0.8052 (4)0.49195 (14)0.0844 (14)
H2O0.789 (5)0.902 (7)0.468 (2)0.067 (15)*
O3A0.7602 (4)0.6985 (4)0.40403 (13)0.0682 (10)
O4A0.8123 (3)0.1958 (4)0.52874 (12)0.0602 (8)
O5A0.7483 (3)0.0822 (4)0.44293 (12)0.0567 (8)
C15B2.1965 (4)1.0427 (6)0.04967 (17)0.0469 (10)
C16B2.1708 (8)0.8816 (7)0.0186 (2)0.095 (2)
H16C2.08780.88680.00150.114*
H16D2.23180.86650.01170.114*
C17B2.1760 (6)0.7325 (6)0.0594 (2)0.0713 (16)
H17C2.09430.71930.07630.086*
H17D2.23700.75470.09210.086*
C18B2.2101 (4)0.5721 (5)0.03051 (17)0.0418 (9)
O2B2.1967 (6)1.1716 (5)0.01417 (18)0.0932 (16)
H3O2.217 (7)1.260 (11)0.029 (3)0.11 (3)*
O3B2.2174 (4)1.0554 (5)0.10135 (14)0.0822 (12)
O4B2.2036 (4)0.5605 (5)0.02416 (13)0.0746 (11)
O5B2.2468 (3)0.4550 (4)0.06510 (13)0.0599 (8)
O1W2.5350 (5)0.4752 (8)0.08517 (19)0.1043 (16)
H1W2.564 (5)0.399 (7)0.112 (3)0.125*
H2W2.4505 (11)0.471 (10)0.086 (3)0.125*
O2W0.4732 (6)0.0040 (13)0.4208 (3)0.153 (3)
H3W0.5572 (13)0.007 (17)0.421 (4)0.184*
H4W0.445 (7)0.034 (14)0.385 (2)0.184*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C1A0.0305 (15)0.0362 (18)0.0264 (15)0.0028 (14)0.0001 (12)0.0024 (13)
C2A0.0347 (17)0.044 (2)0.0310 (16)0.0097 (15)0.0021 (13)0.0036 (15)
C3A0.0347 (16)0.041 (2)0.0267 (15)0.0073 (15)0.0015 (13)0.0005 (14)
C4A0.0377 (18)0.053 (2)0.042 (2)0.0205 (17)0.0030 (15)0.0045 (18)
C5A0.0358 (17)0.067 (3)0.0327 (18)0.0183 (19)0.0051 (14)0.0062 (18)
C6A0.0347 (16)0.0376 (19)0.0297 (16)0.0070 (15)0.0011 (13)0.0039 (14)
C7A0.0325 (16)0.0376 (19)0.0283 (15)0.0003 (14)0.0030 (12)0.0034 (14)
C8A0.0402 (18)0.043 (2)0.0215 (14)0.0008 (15)0.0000 (13)0.0000 (14)
C9A0.0374 (18)0.040 (2)0.0270 (16)0.0036 (15)0.0065 (13)0.0023 (15)
C10A0.0343 (17)0.0322 (17)0.0298 (16)0.0002 (14)0.0013 (13)0.0007 (13)
C11A0.0285 (15)0.0394 (18)0.0231 (14)0.0010 (14)0.0008 (12)0.0003 (13)
C12A0.0363 (17)0.0333 (17)0.0225 (14)0.0014 (14)0.0024 (12)0.0007 (13)
C13A0.0256 (15)0.0387 (19)0.0359 (17)0.0004 (13)0.0035 (13)0.0018 (15)
C14A0.061 (3)0.144 (6)0.055 (3)0.018 (4)0.026 (2)0.029 (4)
N1A0.0388 (16)0.0493 (19)0.0259 (14)0.0045 (14)0.0048 (12)0.0037 (13)
N2A0.053 (2)0.063 (3)0.0310 (16)0.0178 (19)0.0057 (14)0.0017 (16)
N3A0.0286 (15)0.071 (2)0.0367 (17)0.0131 (16)0.0007 (13)0.0075 (17)
O1A0.0311 (12)0.0641 (18)0.0351 (13)0.0101 (12)0.0018 (10)0.0066 (13)
C1B0.0281 (15)0.0341 (17)0.0334 (16)0.0010 (14)0.0032 (13)0.0046 (14)
C2B0.0327 (17)0.049 (2)0.0350 (18)0.0028 (16)0.0055 (14)0.0016 (16)
C3B0.0398 (18)0.037 (2)0.0352 (17)0.0042 (15)0.0019 (14)0.0068 (15)
C4B0.043 (2)0.039 (2)0.057 (2)0.0117 (17)0.0020 (17)0.0052 (19)
C5B0.0333 (18)0.055 (2)0.044 (2)0.0104 (17)0.0085 (15)0.0136 (18)
C6B0.0328 (16)0.0412 (19)0.0336 (17)0.0033 (15)0.0045 (13)0.0118 (15)
C7B0.0349 (17)0.043 (2)0.0323 (17)0.0049 (15)0.0075 (13)0.0103 (15)
C8B0.0458 (19)0.053 (2)0.0232 (15)0.0042 (17)0.0038 (14)0.0005 (15)
C9B0.0413 (18)0.043 (2)0.0302 (17)0.0018 (16)0.0043 (14)0.0023 (15)
C10B0.0302 (16)0.0384 (19)0.0355 (17)0.0019 (14)0.0007 (13)0.0060 (14)
C11B0.0289 (16)0.0410 (19)0.0293 (15)0.0021 (14)0.0021 (12)0.0012 (14)
C12B0.0332 (16)0.0338 (18)0.0286 (16)0.0040 (14)0.0005 (13)0.0040 (14)
C13B0.0268 (15)0.041 (2)0.0369 (17)0.0034 (14)0.0025 (13)0.0053 (16)
C14B0.046 (2)0.092 (4)0.064 (3)0.001 (3)0.017 (2)0.006 (3)
N1B0.0375 (16)0.060 (2)0.0278 (15)0.0010 (15)0.0120 (13)0.0076 (15)
N2B0.0432 (17)0.0451 (18)0.0303 (14)0.0056 (14)0.0007 (13)0.0030 (14)
N3B0.0277 (15)0.080 (3)0.0350 (16)0.0112 (17)0.0004 (13)0.0046 (18)
O1B0.0338 (13)0.074 (2)0.0385 (14)0.0077 (14)0.0053 (11)0.0042 (14)
C15A0.077 (3)0.033 (2)0.0296 (18)0.0066 (19)0.0014 (17)0.0016 (15)
C16A0.174 (6)0.030 (2)0.046 (3)0.004 (3)0.039 (3)0.0034 (19)
C17A0.092 (3)0.037 (2)0.039 (2)0.004 (2)0.000 (2)0.0031 (17)
C18A0.056 (2)0.0314 (18)0.0301 (17)0.0003 (17)0.0158 (15)0.0019 (15)
O2A0.185 (4)0.0330 (17)0.0342 (16)0.003 (2)0.006 (2)0.0019 (13)
O3A0.120 (3)0.0433 (18)0.0390 (16)0.001 (2)0.0224 (17)0.0029 (14)
O4A0.106 (2)0.0444 (17)0.0308 (13)0.0163 (18)0.0061 (14)0.0048 (13)
O5A0.100 (2)0.0350 (15)0.0362 (14)0.0058 (16)0.0127 (15)0.0042 (12)
C15B0.067 (3)0.042 (2)0.0315 (19)0.008 (2)0.0011 (17)0.0040 (17)
C16B0.198 (7)0.041 (3)0.041 (3)0.008 (4)0.029 (3)0.006 (2)
C17B0.135 (5)0.042 (3)0.037 (2)0.005 (3)0.011 (3)0.0016 (19)
C18B0.045 (2)0.049 (2)0.0322 (18)0.0004 (17)0.0096 (15)0.0018 (16)
O2B0.198 (5)0.036 (2)0.0445 (19)0.004 (2)0.001 (2)0.0024 (15)
O3B0.147 (4)0.061 (2)0.0374 (17)0.019 (2)0.0142 (19)0.0044 (16)
O4B0.116 (3)0.069 (2)0.0383 (16)0.034 (2)0.0053 (17)0.0054 (16)
O5B0.099 (2)0.0409 (17)0.0408 (15)0.0037 (17)0.0136 (15)0.0002 (13)
O1W0.121 (4)0.118 (4)0.071 (3)0.001 (3)0.027 (3)0.022 (3)
O2W0.119 (4)0.200 (8)0.137 (5)0.001 (6)0.027 (4)0.050 (6)
Geometric parameters (Å, º) top
C1A—C6A1.356 (5)C5B—H5D0.9700
C1A—C12A1.431 (4)C6B—N1B1.372 (5)
C1A—C2A1.497 (4)C7B—N1B1.354 (5)
C2A—C3A1.514 (5)C7B—C8B1.389 (5)
C2A—H2A0.9700C7B—C12B1.418 (4)
C2A—H2B0.9700C8B—C9B1.373 (5)
C3A—N2A1.504 (5)C8B—H8B0.9300
C3A—C4A1.527 (5)C9B—C10B1.415 (5)
C3A—H3A0.9800C9B—H9B0.9300
C4A—C5A1.538 (5)C10B—C11B1.385 (5)
C4A—H4A0.9700C10B—C13B1.486 (5)
C4A—H4B0.9700C11B—C12B1.392 (4)
C5A—C6A1.495 (5)C11B—H11B0.9300
C5A—H5A0.9700C13B—O1B1.250 (4)
C5A—H5B0.9700C13B—N3B1.320 (5)
C6A—N1A1.369 (4)C14B—N2B1.485 (5)
C7A—N1A1.355 (4)C14B—H14D0.9600
C7A—C8A1.400 (5)C14B—H14E0.9600
C7A—C12A1.412 (4)C14B—H14F0.9600
C8A—C9A1.366 (5)N1B—H6N0.75 (3)
C8A—H8A0.9300N2B—H7N0.99 (5)
C9A—C10A1.409 (5)N2B—H8N0.88 (4)
C9A—H9A0.9300N3B—H9N0.85 (4)
C10A—C11A1.391 (4)N3B—H10N0.86 (3)
C10A—C13A1.486 (4)C15A—O3A1.183 (5)
C11A—C12A1.398 (5)C15A—O2A1.302 (5)
C11A—H11A0.9300C15A—C16A1.486 (6)
C13A—O1A1.253 (4)C16A—C17A1.481 (6)
C13A—N3A1.314 (5)C16A—H16A0.9700
C14A—N2A1.472 (7)C16A—H16B0.9700
C14A—H14A0.9600C17A—C18A1.500 (6)
C14A—H14B0.9600C17A—H17A0.9700
C14A—H14C0.9600C17A—H17B0.9700
N1A—H1N0.81 (5)C18A—O4A1.225 (5)
N2A—H2N0.80 (5)C18A—O5A1.268 (5)
N2A—H3N0.92 (7)O2A—H2O0.96 (6)
N3A—H4N0.86 (4)C15B—O3B1.172 (5)
N3A—H5N0.81 (4)C15B—O2B1.302 (6)
C1B—C6B1.360 (5)C15B—C16B1.483 (7)
C1B—C12B1.427 (5)C16B—C17B1.501 (7)
C1B—C2B1.494 (5)C16B—H16C0.9700
C2B—C3B1.538 (5)C16B—H16D0.9700
C2B—H2C0.9700C17B—C18B1.489 (6)
C2B—H2D0.9700C17B—H17C0.9700
C3B—N2B1.497 (5)C17B—H17D0.9700
C3B—C4B1.524 (5)C18B—O4B1.226 (5)
C3B—H3B0.9800C18B—O5B1.264 (5)
C4B—C5B1.528 (6)O2B—H3O0.81 (9)
C4B—H4C0.9700O1W—H1W0.896 (10)
C4B—H4D0.9700O1W—H2W0.899 (10)
C5B—C6B1.493 (5)O2W—H3W0.893 (11)
C5B—H5C0.9700O2W—H4W0.893 (11)
C6A—C1A—C12A106.7 (3)H4C—C4B—H4D107.5
C6A—C1A—C2A122.7 (3)C6B—C5B—C4B109.5 (3)
C12A—C1A—C2A130.5 (3)C6B—C5B—H5C109.8
C1A—C2A—C3A107.3 (3)C4B—C5B—H5C109.8
C1A—C2A—H2A110.2C6B—C5B—H5D109.8
C3A—C2A—H2A110.2C4B—C5B—H5D109.8
C1A—C2A—H2B110.2H5C—C5B—H5D108.2
C3A—C2A—H2B110.2C1B—C6B—N1B109.5 (3)
H2A—C2A—H2B108.5C1B—C6B—C5B125.3 (3)
N2A—C3A—C2A110.4 (3)N1B—C6B—C5B125.2 (3)
N2A—C3A—C4A109.4 (3)N1B—C7B—C8B131.0 (3)
C2A—C3A—C4A111.3 (3)N1B—C7B—C12B107.3 (3)
N2A—C3A—H3A108.6C8B—C7B—C12B121.8 (3)
C2A—C3A—H3A108.6C9B—C8B—C7B118.2 (3)
C4A—C3A—H3A108.6C9B—C8B—H8B120.9
C3A—C4A—C5A110.5 (3)C7B—C8B—H8B120.9
C3A—C4A—H4A109.5C8B—C9B—C10B121.2 (3)
C5A—C4A—H4A109.5C8B—C9B—H9B119.4
C3A—C4A—H4B109.5C10B—C9B—H9B119.4
C5A—C4A—H4B109.5C11B—C10B—C9B120.3 (3)
H4A—C4A—H4B108.1C11B—C10B—C13B122.1 (3)
C6A—C5A—C4A109.6 (3)C9B—C10B—C13B117.5 (3)
C6A—C5A—H5A109.7C10B—C11B—C12B119.5 (3)
C4A—C5A—H5A109.7C10B—C11B—H11B120.3
C6A—C5A—H5B109.7C12B—C11B—H11B120.3
C4A—C5A—H5B109.7C11B—C12B—C7B119.0 (3)
H5A—C5A—H5B108.2C11B—C12B—C1B134.3 (3)
C1A—C6A—N1A110.3 (3)C7B—C12B—C1B106.6 (3)
C1A—C6A—C5A126.1 (3)O1B—C13B—N3B120.6 (3)
N1A—C6A—C5A123.6 (3)O1B—C13B—C10B120.9 (3)
N1A—C7A—C8A129.6 (3)N3B—C13B—C10B118.5 (3)
N1A—C7A—C12A108.4 (3)N2B—C14B—H14D109.5
C8A—C7A—C12A122.1 (3)N2B—C14B—H14E109.5
C9A—C8A—C7A117.2 (3)H14D—C14B—H14E109.5
C9A—C8A—H8A121.4N2B—C14B—H14F109.5
C7A—C8A—H8A121.4H14D—C14B—H14F109.5
C8A—C9A—C10A122.5 (3)H14E—C14B—H14F109.5
C8A—C9A—H9A118.8C7B—N1B—C6B109.7 (3)
C10A—C9A—H9A118.8C7B—N1B—H6N124 (3)
C11A—C10A—C9A120.0 (3)C6B—N1B—H6N127 (3)
C11A—C10A—C13A122.6 (3)C14B—N2B—C3B115.1 (4)
C9A—C10A—C13A117.4 (3)C14B—N2B—H7N112 (2)
C10A—C11A—C12A119.1 (3)C3B—N2B—H7N108 (2)
C10A—C11A—H11A120.5C14B—N2B—H8N110 (3)
C12A—C11A—H11A120.5C3B—N2B—H8N105 (3)
C11A—C12A—C7A119.2 (3)H7N—N2B—H8N107 (4)
C11A—C12A—C1A134.7 (3)C13B—N3B—H9N123 (3)
C7A—C12A—C1A106.1 (3)C13B—N3B—H10N118 (2)
O1A—C13A—N3A120.2 (3)H9N—N3B—H10N118 (4)
O1A—C13A—C10A119.9 (3)O3A—C15A—O2A122.7 (4)
N3A—C13A—C10A119.8 (3)O3A—C15A—C16A124.0 (4)
N2A—C14A—H14A109.5O2A—C15A—C16A113.2 (3)
N2A—C14A—H14B109.5C17A—C16A—C15A115.2 (4)
H14A—C14A—H14B109.5C17A—C16A—H16A108.5
N2A—C14A—H14C109.5C15A—C16A—H16A108.5
H14A—C14A—H14C109.5C17A—C16A—H16B108.5
H14B—C14A—H14C109.5C15A—C16A—H16B108.5
C7A—N1A—C6A108.6 (3)H16A—C16A—H16B107.5
C7A—N1A—H1N122 (3)C16A—C17A—C18A115.1 (4)
C6A—N1A—H1N129 (3)C16A—C17A—H17A108.5
C14A—N2A—C3A114.6 (4)C18A—C17A—H17A108.5
C14A—N2A—H2N104 (3)C16A—C17A—H17B108.5
C3A—N2A—H2N107 (3)C18A—C17A—H17B108.5
C14A—N2A—H3N105 (4)H17A—C17A—H17B107.5
C3A—N2A—H3N113 (4)O4A—C18A—O5A124.0 (4)
H2N—N2A—H3N112 (5)O4A—C18A—C17A119.6 (4)
C13A—N3A—H4N120 (2)O5A—C18A—C17A116.4 (3)
C13A—N3A—H5N119 (3)C15A—O2A—H2O105 (3)
H4N—N3A—H5N117 (4)O3B—C15B—O2B121.9 (4)
C6B—C1B—C12B106.9 (3)O3B—C15B—C16B124.1 (4)
C6B—C1B—C2B123.6 (3)O2B—C15B—C16B114.0 (4)
C12B—C1B—C2B129.4 (3)C15B—C16B—C17B113.8 (4)
C1B—C2B—C3B112.1 (3)C15B—C16B—H16C108.8
C1B—C2B—H2C109.2C17B—C16B—H16C108.8
C3B—C2B—H2C109.2C15B—C16B—H16D108.8
C1B—C2B—H2D109.2C17B—C16B—H16D108.8
C3B—C2B—H2D109.2H16C—C16B—H16D107.7
H2C—C2B—H2D107.9C18B—C17B—C16B115.0 (4)
N2B—C3B—C4B111.9 (3)C18B—C17B—H17C108.5
N2B—C3B—C2B108.7 (3)C16B—C17B—H17C108.5
C4B—C3B—C2B112.1 (3)C18B—C17B—H17D108.5
N2B—C3B—H3B108.0C16B—C17B—H17D108.5
C4B—C3B—H3B108.0H17C—C17B—H17D107.5
C2B—C3B—H3B108.0O4B—C18B—O5B123.8 (4)
C3B—C4B—C5B114.8 (3)O4B—C18B—C17B119.7 (4)
C3B—C4B—H4C108.6O5B—C18B—C17B116.5 (4)
C5B—C4B—H4C108.6C15B—O2B—H3O116 (5)
C3B—C4B—H4D108.6H1W—O1W—H2W106.0 (17)
C5B—C4B—H4D108.6H3W—O2W—H4W107.6 (17)
C6A—C1A—C2A—C3A21.6 (5)C2B—C3B—C4B—C5B56.5 (5)
C12A—C1A—C2A—C3A153.0 (4)C3B—C4B—C5B—C6B42.9 (5)
C1A—C2A—C3A—N2A176.4 (3)C12B—C1B—C6B—N1B0.3 (4)
C1A—C2A—C3A—C4A54.7 (4)C2B—C1B—C6B—N1B177.5 (3)
N2A—C3A—C4A—C5A171.3 (3)C12B—C1B—C6B—C5B178.5 (4)
C2A—C3A—C4A—C5A66.5 (4)C2B—C1B—C6B—C5B1.3 (6)
C3A—C4A—C5A—C6A38.7 (5)C4B—C5B—C6B—C1B15.8 (6)
C12A—C1A—C6A—N1A1.2 (4)C4B—C5B—C6B—N1B162.8 (4)
C2A—C1A—C6A—N1A176.9 (3)N1B—C7B—C8B—C9B179.7 (4)
C12A—C1A—C6A—C5A178.1 (4)C12B—C7B—C8B—C9B0.0 (6)
C2A—C1A—C6A—C5A2.4 (6)C7B—C8B—C9B—C10B0.5 (6)
C4A—C5A—C6A—C1A6.3 (6)C8B—C9B—C10B—C11B0.1 (6)
C4A—C5A—C6A—N1A174.4 (4)C8B—C9B—C10B—C13B178.1 (4)
N1A—C7A—C8A—C9A179.2 (4)C9B—C10B—C11B—C12B0.8 (5)
C12A—C7A—C8A—C9A1.1 (6)C13B—C10B—C11B—C12B178.9 (4)
C7A—C8A—C9A—C10A1.5 (6)C10B—C11B—C12B—C7B1.3 (5)
C8A—C9A—C10A—C11A0.9 (6)C10B—C11B—C12B—C1B179.7 (4)
C8A—C9A—C10A—C13A179.5 (4)N1B—C7B—C12B—C11B179.4 (3)
C9A—C10A—C11A—C12A0.3 (5)C8B—C7B—C12B—C11B0.9 (6)
C13A—C10A—C11A—C12A179.3 (3)N1B—C7B—C12B—C1B0.1 (4)
C10A—C11A—C12A—C7A0.7 (5)C8B—C7B—C12B—C1B179.8 (4)
C10A—C11A—C12A—C1A179.7 (4)C6B—C1B—C12B—C11B179.4 (4)
N1A—C7A—C12A—C11A179.7 (3)C2B—C1B—C12B—C11B3.7 (7)
C8A—C7A—C12A—C11A0.0 (5)C6B—C1B—C12B—C7B0.2 (4)
N1A—C7A—C12A—C1A0.0 (4)C2B—C1B—C12B—C7B177.2 (4)
C8A—C7A—C12A—C1A179.7 (3)C11B—C10B—C13B—O1B165.3 (4)
C6A—C1A—C12A—C11A178.9 (4)C9B—C10B—C13B—O1B16.6 (6)
C2A—C1A—C12A—C11A3.7 (7)C11B—C10B—C13B—N3B13.9 (6)
C6A—C1A—C12A—C7A0.7 (4)C9B—C10B—C13B—N3B164.3 (4)
C2A—C1A—C12A—C7A176.0 (4)C8B—C7B—N1B—C6B179.6 (4)
C11A—C10A—C13A—O1A179.3 (4)C12B—C7B—N1B—C6B0.1 (4)
C9A—C10A—C13A—O1A1.1 (5)C1B—C6B—N1B—C7B0.3 (5)
C11A—C10A—C13A—N3A2.0 (6)C5B—C6B—N1B—C7B178.5 (4)
C9A—C10A—C13A—N3A177.6 (4)C4B—C3B—N2B—C14B62.2 (4)
C8A—C7A—N1A—C6A179.0 (4)C2B—C3B—N2B—C14B173.5 (3)
C12A—C7A—N1A—C6A0.7 (4)O3A—C15A—C16A—C17A4.0 (9)
C1A—C6A—N1A—C7A1.2 (4)O2A—C15A—C16A—C17A177.9 (6)
C5A—C6A—N1A—C7A178.1 (4)C15A—C16A—C17A—C18A160.3 (5)
C2A—C3A—N2A—C14A164.0 (4)C16A—C17A—C18A—O4A11.0 (7)
C4A—C3A—N2A—C14A73.2 (5)C16A—C17A—C18A—O5A169.1 (5)
C6B—C1B—C2B—C3B12.8 (5)O3B—C15B—C16B—C17B1.0 (10)
C12B—C1B—C2B—C3B170.6 (4)O2B—C15B—C16B—C17B177.6 (6)
C1B—C2B—C3B—N2B85.4 (4)C15B—C16B—C17B—C18B152.9 (6)
C1B—C2B—C3B—C4B38.8 (5)C16B—C17B—C18B—O4B16.4 (8)
N2B—C3B—C4B—C5B65.9 (4)C16B—C17B—C18B—O5B162.4 (5)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1A—H1N···O5A0.81 (5)2.08 (5)2.854 (4)161 (4)
N2A—H2N···O4Bi0.80 (5)1.92 (5)2.707 (5)167 (5)
N2A—H3N···O1Wii0.92 (7)2.43 (7)3.172 (7)138 (5)
N3A—H4N···O3Biii0.86 (4)2.06 (4)2.884 (5)161 (3)
N3A—H5N···O1B0.81 (4)2.12 (4)2.923 (4)178 (4)
N1B—H6N···O5B0.75 (3)2.23 (4)2.952 (4)161 (3)
N2B—H7N···O1Aiv0.99 (5)1.94 (5)2.858 (5)154 (3)
N2B—H8N···O4Av0.88 (4)1.85 (5)2.703 (4)164 (4)
N3B—H9N···O3Avi0.85 (4)2.07 (4)2.871 (4)159 (4)
N3B—H10N···O1A0.86 (3)2.03 (3)2.887 (4)175 (3)
O2A—H2O···O5Avii0.96 (6)1.60 (6)2.538 (5)167 (5)
O2B—H3O···O5Bviii0.81 (9)1.77 (9)2.580 (5)175 (8)
O1W—H1W···O1Biv0.90 (1)1.98 (3)2.835 (5)158 (6)
O1W—H2W···O5B0.90 (1)2.19 (2)3.076 (6)167 (6)
O2W—H3W···O5A0.89 (1)2.15 (3)3.004 (8)160 (9)
O2W—H4W···O1Aix0.89 (1)2.22 (4)3.086 (7)163 (11)
C3A—H3A···O1Bix0.982.573.547 (5)171
C3B—H3B···O2Ax0.982.573.344 (5)136
C9A—H9A···O4Axi0.932.583.300 (4)135
C11A—H11A···O3Biii0.932.553.451 (5)164
Symmetry codes: (i) x+3, y+1/2, z; (ii) x2, y+1, z; (iii) x1, y+1, z; (iv) x+1, y, z; (v) x+3, y1/2, z+1; (vi) x+1, y1, z; (vii) x, y+1, z; (viii) x, y1, z; (ix) x1, y, z; (x) x+3, y3/2, z+1; (xi) x+2, y1/2, z+1.
(III) Bis[(R)-(+)-6-carbamoyl-N-methyl-2,3,4,9-tetrahydro-1H-carbazol-3-aminium] succinate trihydrate top
Crystal data top
2C14H18N3O+·C4H4O42·3H2OF(000) = 704
Mr = 658.75Dx = 1.334 Mg m3
Monoclinic, P21Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ybCell parameters from 8568 reflections
a = 8.7239 (11) Åθ = 2.2–27.2°
b = 18.662 (2) ŵ = 0.10 mm1
c = 10.1270 (13) ÅT = 294 K
β = 96.098 (2)°Plate, colorless
V = 1639.4 (4) Å30.15 × 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 tubeRint = 0.025
Graphite monochromatorθmax = 28.3°, θmin = 2.0°
ω scanh = 1111
19224 measured reflectionsk = 2424
4082 independent reflectionsl = 1313
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.041Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.102H 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 parametersΔρmax = 0.27 e Å3
1 restraintΔρmin = 0.22 e Å3
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
xyzUiso*/Ueq
C1A0.4446 (3)0.77615 (12)1.9076 (2)0.0304 (4)
C2A0.4601 (3)0.69807 (12)1.9390 (2)0.0334 (5)
H2A0.37170.67171.91420.040*
H2B0.55250.67851.89040.040*
C3A0.4693 (3)0.69225 (13)2.0886 (2)0.0320 (4)
H3A0.37250.71062.13400.038*
C4A0.6000 (3)0.73850 (15)2.1294 (3)0.0429 (6)
H4A0.61670.72812.22060.051*
H4B0.69430.72782.07330.051*
C5A0.5591 (3)0.81765 (15)2.1161 (2)0.0450 (6)
H5A0.65150.84672.11550.054*
H5B0.48760.83222.19120.054*
C6A0.4872 (3)0.82889 (13)1.9894 (2)0.0344 (5)
C7A0.3819 (3)0.88573 (12)1.8276 (2)0.0327 (4)
C8A0.3243 (3)0.93631 (12)1.7440 (2)0.0380 (5)
H8A0.32570.98501.76340.046*
C9A0.2654 (3)0.91144 (13)1.6315 (2)0.0363 (5)
H9A0.22580.94411.57470.044*
C10A0.2635 (2)0.83812 (12)1.6001 (2)0.0304 (4)
C11A0.3186 (2)0.78780 (12)1.6847 (2)0.0295 (4)
H11A0.31540.73921.66490.035*
C12A0.3789 (2)0.81112 (12)1.8000 (2)0.0295 (4)
C13A0.2025 (3)0.81756 (14)1.4730 (2)0.0339 (5)
C14A0.3432 (3)0.57385 (16)2.1367 (3)0.0491 (6)
H14A0.26390.59722.19420.074*
H14B0.31150.57032.04900.074*
H14C0.36050.52672.16990.074*
N1A0.4500 (3)0.89484 (11)1.9424 (2)0.0386 (5)
H1N0.458 (4)0.932 (2)1.987 (4)0.055 (9)*
N2A0.4877 (3)0.61616 (12)2.1320 (2)0.0377 (4)
H2N0.557 (4)0.5960 (18)2.079 (3)0.042 (8)*
H3N0.516 (3)0.6167 (17)2.211 (3)0.043 (8)*
N3A0.2314 (3)0.75275 (14)1.4222 (2)0.0465 (5)
H4N0.190 (4)0.7403 (18)1.349 (3)0.050 (9)*
H5N0.290 (4)0.727 (2)1.456 (4)0.065 (11)*
O1A0.1276 (2)0.86175 (11)1.41300 (18)0.0454 (4)
C1B0.1732 (3)0.83382 (13)0.6745 (2)0.0330 (5)
C2B0.2243 (3)0.91011 (13)0.6800 (2)0.0368 (5)
H2C0.31510.91490.74350.044*
H2D0.14350.93980.70990.044*
C3B0.2618 (3)0.93602 (13)0.5430 (2)0.0339 (5)
H3B0.32880.97810.55630.041*
C4B0.3465 (3)0.87943 (16)0.4701 (3)0.0434 (6)
H4C0.44620.87090.51970.052*
H4D0.36480.89830.38390.052*
C5B0.2624 (3)0.80789 (15)0.4496 (2)0.0437 (6)
H5C0.18120.81190.37670.052*
H5D0.33390.77110.42730.052*
C6B0.1949 (3)0.78772 (14)0.5737 (2)0.0358 (5)
C7B0.0851 (3)0.72234 (13)0.7231 (2)0.0353 (5)
C8B0.0208 (3)0.66868 (13)0.7962 (3)0.0406 (5)
H8B0.00990.62200.76430.049*
C9B0.0259 (3)0.68742 (14)0.9179 (2)0.0382 (5)
H9B0.06780.65240.96870.046*
C10B0.0121 (3)0.75785 (13)0.9670 (2)0.0320 (4)
C11B0.0521 (3)0.81131 (12)0.8943 (2)0.0315 (4)
H11B0.06140.85800.92640.038*
C12B0.1023 (3)0.79327 (12)0.7720 (2)0.0311 (4)
C13B0.0638 (3)0.77314 (13)1.1004 (2)0.0347 (5)
C14B0.0560 (3)1.02880 (17)0.5018 (3)0.0539 (7)
H14D0.13221.06520.49380.081*
H14E0.03331.02610.59240.081*
H14F0.03631.04050.44570.081*
N1B0.1411 (3)0.72066 (12)0.6011 (2)0.0405 (5)
H6N0.148 (4)0.685 (2)0.557 (3)0.053 (9)*
N2B0.1159 (2)0.95862 (12)0.4610 (2)0.0349 (4)
H7N0.129 (4)0.9635 (18)0.374 (3)0.049 (8)*
H8N0.045 (3)0.9270 (15)0.463 (3)0.030 (6)*
N3B0.0908 (3)0.84089 (14)1.1313 (2)0.0474 (5)
H9N0.087 (4)0.876 (2)1.078 (4)0.062 (10)*
H10N0.115 (3)0.8496 (18)1.214 (3)0.045 (8)*
O1B0.0814 (2)0.72355 (10)1.18003 (18)0.0457 (4)
C150.5804 (3)0.52770 (13)1.8348 (2)0.0354 (5)
C160.6405 (3)0.54890 (18)1.6945 (2)0.0496 (7)
H16A0.67520.50601.64600.059*
H16B0.72940.57981.69810.059*
C170.5267 (3)0.5866 (2)1.6192 (3)0.0527 (7)
H17A0.43590.55651.61960.063*
H17B0.49550.63031.66620.063*
C180.5816 (3)0.60582 (13)1.4753 (2)0.0379 (5)
O20.4551 (3)0.49700 (14)1.8557 (2)0.0637 (6)
O30.6627 (2)0.54062 (12)1.92618 (18)0.0513 (5)
O40.7231 (2)0.60742 (12)1.44164 (18)0.0498 (5)
O50.4786 (3)0.61995 (17)1.4030 (2)0.0700 (7)
O1W0.0589 (3)0.99504 (13)1.0043 (2)0.0516 (5)
H1W0.136 (5)1.011 (2)1.030 (4)0.068 (12)*
H2W0.057 (3)1.0184 (19)0.935 (4)0.046 (9)*
O2W0.1686 (3)0.9908 (2)1.2112 (2)0.0827 (10)
H3W0.099 (6)0.993 (3)1.151 (5)0.098 (16)*
H4W0.259 (5)0.993 (2)1.190 (4)0.069 (11)*
O3W0.0818 (4)1.09156 (15)0.7882 (3)0.0763 (8)
H5W0.151 (5)1.099 (2)0.729 (4)0.062 (11)*
H6W0.043 (5)1.135 (2)0.801 (4)0.074 (12)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C1A0.0391 (11)0.0295 (11)0.0233 (9)0.0009 (8)0.0065 (8)0.0005 (8)
C2A0.0495 (13)0.0287 (10)0.0236 (9)0.0016 (9)0.0110 (9)0.0005 (8)
C3A0.0385 (11)0.0355 (11)0.0226 (9)0.0037 (9)0.0064 (8)0.0023 (8)
C4A0.0504 (14)0.0488 (15)0.0326 (11)0.0040 (11)0.0190 (10)0.0026 (10)
C5A0.0615 (16)0.0470 (14)0.0292 (11)0.0103 (12)0.0183 (11)0.0032 (10)
C6A0.0444 (12)0.0346 (11)0.0244 (10)0.0040 (9)0.0048 (8)0.0009 (8)
C7A0.0391 (11)0.0305 (11)0.0277 (10)0.0006 (9)0.0004 (8)0.0011 (9)
C8A0.0489 (13)0.0254 (10)0.0389 (12)0.0036 (9)0.0012 (10)0.0002 (9)
C9A0.0397 (11)0.0346 (11)0.0348 (11)0.0061 (9)0.0046 (9)0.0067 (9)
C10A0.0294 (10)0.0354 (11)0.0267 (10)0.0009 (8)0.0042 (8)0.0022 (8)
C11A0.0336 (10)0.0284 (10)0.0272 (9)0.0005 (8)0.0063 (8)0.0011 (8)
C12A0.0335 (10)0.0290 (10)0.0259 (9)0.0001 (8)0.0034 (8)0.0013 (8)
C13A0.0302 (10)0.0470 (13)0.0249 (10)0.0029 (9)0.0047 (8)0.0033 (9)
C14A0.0598 (16)0.0396 (13)0.0468 (14)0.0033 (12)0.0009 (12)0.0101 (11)
N1A0.0565 (12)0.0300 (10)0.0299 (10)0.0033 (9)0.0073 (8)0.0051 (8)
N2A0.0484 (11)0.0406 (11)0.0242 (9)0.0095 (9)0.0042 (8)0.0059 (8)
N3A0.0584 (14)0.0480 (13)0.0369 (11)0.0100 (11)0.0220 (10)0.0040 (10)
O1A0.0491 (10)0.0564 (11)0.0326 (9)0.0177 (9)0.0130 (7)0.0013 (8)
C1B0.0378 (11)0.0373 (11)0.0246 (9)0.0035 (9)0.0055 (8)0.0031 (8)
C2B0.0446 (12)0.0374 (12)0.0286 (10)0.0001 (10)0.0056 (9)0.0011 (9)
C3B0.0306 (10)0.0397 (12)0.0316 (11)0.0035 (9)0.0048 (8)0.0042 (9)
C4B0.0374 (12)0.0546 (15)0.0405 (13)0.0065 (11)0.0144 (10)0.0068 (11)
C5B0.0567 (15)0.0468 (14)0.0300 (11)0.0110 (12)0.0161 (10)0.0004 (10)
C6B0.0424 (12)0.0370 (12)0.0290 (10)0.0084 (10)0.0078 (9)0.0006 (9)
C7B0.0423 (12)0.0334 (11)0.0303 (11)0.0067 (9)0.0045 (9)0.0026 (9)
C8B0.0524 (14)0.0302 (11)0.0402 (12)0.0009 (10)0.0088 (10)0.0018 (10)
C9B0.0440 (12)0.0355 (12)0.0365 (11)0.0002 (10)0.0108 (10)0.0052 (10)
C10B0.0341 (10)0.0360 (11)0.0265 (10)0.0030 (9)0.0056 (8)0.0018 (8)
C11B0.0378 (11)0.0305 (10)0.0267 (10)0.0021 (9)0.0054 (8)0.0017 (8)
C12B0.0346 (10)0.0319 (11)0.0269 (10)0.0045 (8)0.0037 (8)0.0016 (8)
C13B0.0340 (10)0.0422 (13)0.0290 (10)0.0003 (9)0.0081 (8)0.0023 (9)
C14B0.0510 (15)0.0509 (16)0.0601 (17)0.0110 (13)0.0074 (13)0.0052 (14)
N1B0.0594 (13)0.0338 (10)0.0301 (10)0.0071 (9)0.0130 (9)0.0050 (8)
N2B0.0328 (9)0.0389 (10)0.0335 (10)0.0025 (8)0.0057 (8)0.0045 (8)
N3B0.0698 (15)0.0424 (12)0.0336 (11)0.0032 (11)0.0220 (10)0.0002 (10)
O1B0.0598 (11)0.0434 (10)0.0372 (9)0.0017 (9)0.0198 (8)0.0061 (8)
C150.0391 (11)0.0325 (11)0.0346 (11)0.0057 (9)0.0043 (9)0.0064 (9)
C160.0469 (13)0.0672 (18)0.0336 (12)0.0073 (13)0.0001 (10)0.0125 (12)
C170.0465 (14)0.084 (2)0.0275 (11)0.0108 (14)0.0035 (10)0.0141 (12)
C180.0516 (13)0.0390 (12)0.0236 (10)0.0035 (10)0.0067 (9)0.0017 (9)
O20.0551 (12)0.0796 (16)0.0574 (13)0.0200 (11)0.0100 (10)0.0230 (12)
O30.0499 (10)0.0665 (13)0.0393 (9)0.0131 (9)0.0132 (8)0.0027 (9)
O40.0563 (11)0.0581 (12)0.0337 (9)0.0077 (9)0.0020 (8)0.0015 (8)
O50.0714 (14)0.107 (2)0.0336 (10)0.0011 (14)0.0171 (9)0.0193 (12)
O1W0.0471 (11)0.0607 (13)0.0470 (11)0.0123 (10)0.0051 (9)0.0073 (10)
O2W0.0476 (13)0.159 (3)0.0417 (12)0.0034 (16)0.0062 (10)0.0293 (15)
O3W0.112 (2)0.0581 (15)0.0516 (13)0.0239 (15)0.0258 (14)0.0098 (11)
Geometric parameters (Å, º) top
C1A—C6A1.363 (3)C4B—C5B1.527 (4)
C1A—C12A1.441 (3)C4B—H4C0.9700
C1A—C2A1.500 (3)C4B—H4D0.9700
C2A—C3A1.530 (3)C5B—C6B1.492 (3)
C2A—H2A0.9700C5B—H5C0.9700
C2A—H2B0.9700C5B—H5D0.9700
C3A—N2A1.500 (3)C6B—N1B1.375 (3)
C3A—C4A1.522 (3)C7B—N1B1.376 (3)
C3A—H3A0.9800C7B—C8B1.398 (3)
C4A—C5A1.529 (4)C7B—C12B1.416 (3)
C4A—H4A0.9700C8B—C9B1.383 (4)
C4A—H4B0.9700C8B—H8B0.9300
C5A—C6A1.502 (3)C9B—C10B1.406 (3)
C5A—H5A0.9700C9B—H9B0.9300
C5A—H5B0.9700C10B—C11B1.393 (3)
C6A—N1A1.371 (3)C10B—C13B1.496 (3)
C7A—N1A1.371 (3)C11B—C12B1.398 (3)
C7A—C8A1.397 (3)C11B—H11B0.9300
C7A—C12A1.421 (3)C13B—O1B1.248 (3)
C8A—C9A1.379 (3)C13B—N3B1.330 (3)
C8A—H8A0.9300C14B—N2B1.485 (4)
C9A—C10A1.405 (3)C14B—H14D0.9600
C9A—H9A0.9300C14B—H14E0.9600
C10A—C11A1.390 (3)C14B—H14F0.9600
C10A—C13A1.494 (3)N1B—H6N0.81 (4)
C11A—C12A1.400 (3)N2B—H7N0.90 (3)
C11A—H11A0.9300N2B—H8N0.86 (3)
C13A—O1A1.250 (3)N3B—H9N0.85 (4)
C13A—N3A1.328 (3)N3B—H10N0.89 (3)
C14A—N2A1.485 (4)C15—O21.232 (3)
C14A—H14A0.9600C15—O31.254 (3)
C14A—H14B0.9600C15—C161.514 (3)
C14A—H14C0.9600C16—C171.491 (4)
N1A—H1N0.84 (4)C16—H16A0.9700
N2A—H2N0.85 (3)C16—H16B0.9700
N2A—H3N0.87 (3)C17—C181.527 (3)
N3A—H4N0.89 (3)C17—H17A0.9700
N3A—H5N0.81 (4)C17—H17B0.9700
C1B—C6B1.364 (3)C18—O41.246 (3)
C1B—C12B1.435 (3)C18—O51.246 (3)
C1B—C2B1.491 (3)O1W—H1W0.81 (4)
C2B—C3B1.537 (3)O1W—H2W0.83 (4)
C2B—H2C0.9700O2W—H3W0.82 (6)
C2B—H2D0.9700O2W—H4W0.84 (4)
C3B—N2B1.504 (3)O3W—H5W0.82 (4)
C3B—C4B1.524 (4)O3W—H6W0.89 (5)
C3B—H3B0.9800
C6A—C1A—C12A106.8 (2)C4B—C3B—C2B112.3 (2)
C6A—C1A—C2A122.4 (2)N2B—C3B—H3B108.0
C12A—C1A—C2A130.7 (2)C4B—C3B—H3B108.0
C1A—C2A—C3A107.08 (18)C2B—C3B—H3B108.0
C1A—C2A—H2A110.3C3B—C4B—C5B114.9 (2)
C3A—C2A—H2A110.3C3B—C4B—H4C108.5
C1A—C2A—H2B110.3C5B—C4B—H4C108.5
C3A—C2A—H2B110.3C3B—C4B—H4D108.5
H2A—C2A—H2B108.6C5B—C4B—H4D108.5
N2A—C3A—C4A110.51 (19)H4C—C4B—H4D107.5
N2A—C3A—C2A112.09 (19)C6B—C5B—C4B109.5 (2)
C4A—C3A—C2A110.4 (2)C6B—C5B—H5C109.8
N2A—C3A—H3A107.9C4B—C5B—H5C109.8
C4A—C3A—H3A107.9C6B—C5B—H5D109.8
C2A—C3A—H3A107.9C4B—C5B—H5D109.8
C3A—C4A—C5A109.6 (2)H5C—C5B—H5D108.2
C3A—C4A—H4A109.7C1B—C6B—N1B110.2 (2)
C5A—C4A—H4A109.7C1B—C6B—C5B124.8 (2)
C3A—C4A—H4B109.7N1B—C6B—C5B125.0 (2)
C5A—C4A—H4B109.7N1B—C7B—C8B131.3 (2)
H4A—C4A—H4B108.2N1B—C7B—C12B107.5 (2)
C6A—C5A—C4A109.4 (2)C8B—C7B—C12B121.2 (2)
C6A—C5A—H5A109.8C9B—C8B—C7B117.6 (2)
C4A—C5A—H5A109.8C9B—C8B—H8B121.2
C6A—C5A—H5B109.8C7B—C8B—H8B121.2
C4A—C5A—H5B109.8C8B—C9B—C10B121.9 (2)
H5A—C5A—H5B108.2C8B—C9B—H9B119.0
C1A—C6A—N1A110.3 (2)C10B—C9B—H9B119.0
C1A—C6A—C5A125.7 (2)C11B—C10B—C9B120.5 (2)
N1A—C6A—C5A123.9 (2)C11B—C10B—C13B121.2 (2)
N1A—C7A—C8A130.3 (2)C9B—C10B—C13B118.3 (2)
N1A—C7A—C12A107.9 (2)C10B—C11B—C12B118.5 (2)
C8A—C7A—C12A121.8 (2)C10B—C11B—H11B120.7
C9A—C8A—C7A117.6 (2)C12B—C11B—H11B120.7
C9A—C8A—H8A121.2C11B—C12B—C7B120.2 (2)
C7A—C8A—H8A121.2C11B—C12B—C1B132.9 (2)
C8A—C9A—C10A121.9 (2)C7B—C12B—C1B106.9 (2)
C8A—C9A—H9A119.0O1B—C13B—N3B121.0 (2)
C10A—C9A—H9A119.0O1B—C13B—C10B120.8 (2)
C11A—C10A—C9A120.4 (2)N3B—C13B—C10B118.2 (2)
C11A—C10A—C13A122.4 (2)N2B—C14B—H14D109.5
C9A—C10A—C13A117.3 (2)N2B—C14B—H14E109.5
C10A—C11A—C12A119.3 (2)H14D—C14B—H14E109.5
C10A—C11A—H11A120.4N2B—C14B—H14F109.5
C12A—C11A—H11A120.4H14D—C14B—H14F109.5
C11A—C12A—C7A119.0 (2)H14E—C14B—H14F109.5
C11A—C12A—C1A134.8 (2)C6B—N1B—C7B108.8 (2)
C7A—C12A—C1A106.13 (19)C6B—N1B—H6N126 (3)
O1A—C13A—N3A120.0 (2)C7B—N1B—H6N125 (3)
O1A—C13A—C10A120.1 (2)C14B—N2B—C3B113.3 (2)
N3A—C13A—C10A119.8 (2)C14B—N2B—H7N105 (2)
N2A—C14A—H14A109.5C3B—N2B—H7N112 (2)
N2A—C14A—H14B109.5C14B—N2B—H8N108.8 (17)
H14A—C14A—H14B109.5C3B—N2B—H8N111.3 (18)
N2A—C14A—H14C109.5H7N—N2B—H8N105 (3)
H14A—C14A—H14C109.5C13B—N3B—H9N125 (3)
H14B—C14A—H14C109.5C13B—N3B—H10N117 (2)
C6A—N1A—C7A108.85 (19)H9N—N3B—H10N118 (3)
C6A—N1A—H1N122 (2)O2—C15—O3121.9 (2)
C7A—N1A—H1N129 (2)O2—C15—C16119.7 (2)
C14A—N2A—C3A113.3 (2)O3—C15—C16118.3 (2)
C14A—N2A—H2N109 (2)C17—C16—C15114.8 (2)
C3A—N2A—H2N109 (2)C17—C16—H16A108.6
C14A—N2A—H3N108 (2)C15—C16—H16A108.6
C3A—N2A—H3N108 (2)C17—C16—H16B108.6
H2N—N2A—H3N110 (3)C15—C16—H16B108.6
C13A—N3A—H4N119 (2)H16A—C16—H16B107.5
C13A—N3A—H5N119 (3)C16—C17—C18116.1 (2)
H4N—N3A—H5N122 (4)C16—C17—H17A108.2
C6B—C1B—C12B106.7 (2)C18—C17—H17A108.2
C6B—C1B—C2B124.5 (2)C16—C17—H17B108.2
C12B—C1B—C2B128.8 (2)C18—C17—H17B108.2
C1B—C2B—C3B110.97 (19)H17A—C17—H17B107.4
C1B—C2B—H2C109.4O4—C18—O5126.1 (2)
C3B—C2B—H2C109.4O4—C18—C17117.9 (2)
C1B—C2B—H2D109.4O5—C18—C17116.0 (2)
C3B—C2B—H2D109.4H1W—O1W—H2W100 (4)
H2C—C2B—H2D108.0H3W—O2W—H4W117 (4)
N2B—C3B—C4B110.7 (2)H5W—O3W—H6W101 (4)
N2B—C3B—C2B109.73 (18)
C6A—C1A—C2A—C3A20.8 (3)C1B—C2B—C3B—C4B40.5 (3)
C12A—C1A—C2A—C3A155.0 (2)N2B—C3B—C4B—C5B66.0 (3)
C1A—C2A—C3A—N2A179.06 (19)C2B—C3B—C4B—C5B57.0 (3)
C1A—C2A—C3A—C4A55.4 (3)C3B—C4B—C5B—C6B42.7 (3)
N2A—C3A—C4A—C5A166.0 (2)C12B—C1B—C6B—N1B0.4 (3)
C2A—C3A—C4A—C5A69.4 (3)C2B—C1B—C6B—N1B177.2 (2)
C3A—C4A—C5A—C6A42.2 (3)C12B—C1B—C6B—C5B178.5 (2)
C12A—C1A—C6A—N1A1.3 (3)C2B—C1B—C6B—C5B4.6 (4)
C2A—C1A—C6A—N1A175.4 (2)C4B—C5B—C6B—C1B17.0 (3)
C12A—C1A—C6A—C5A179.0 (2)C4B—C5B—C6B—N1B165.1 (2)
C2A—C1A—C6A—C5A2.4 (4)N1B—C7B—C8B—C9B179.8 (2)
C4A—C5A—C6A—C1A8.5 (4)C12B—C7B—C8B—C9B0.3 (4)
C4A—C5A—C6A—N1A174.0 (2)C7B—C8B—C9B—C10B0.8 (4)
N1A—C7A—C8A—C9A178.1 (2)C8B—C9B—C10B—C11B0.9 (4)
C12A—C7A—C8A—C9A0.8 (4)C8B—C9B—C10B—C13B179.2 (2)
C7A—C8A—C9A—C10A0.5 (4)C9B—C10B—C11B—C12B0.1 (3)
C8A—C9A—C10A—C11A1.5 (3)C13B—C10B—C11B—C12B178.2 (2)
C8A—C9A—C10A—C13A177.7 (2)C10B—C11B—C12B—C7B1.1 (3)
C9A—C10A—C11A—C12A1.3 (3)C10B—C11B—C12B—C1B179.4 (2)
C13A—C10A—C11A—C12A177.9 (2)N1B—C7B—C12B—C11B178.8 (2)
C10A—C11A—C12A—C7A0.1 (3)C8B—C7B—C12B—C11B1.2 (4)
C10A—C11A—C12A—C1A179.9 (2)N1B—C7B—C12B—C1B0.8 (3)
N1A—C7A—C12A—C11A178.10 (19)C8B—C7B—C12B—C1B179.1 (2)
C8A—C7A—C12A—C11A1.0 (3)C6B—C1B—C12B—C11B179.3 (2)
N1A—C7A—C12A—C1A1.9 (3)C2B—C1B—C12B—C11B4.0 (4)
C8A—C7A—C12A—C1A179.0 (2)C6B—C1B—C12B—C7B0.3 (3)
C6A—C1A—C12A—C11A178.1 (2)C2B—C1B—C12B—C7B176.4 (2)
C2A—C1A—C12A—C11A5.7 (5)C11B—C10B—C13B—O1B160.4 (2)
C6A—C1A—C12A—C7A1.9 (3)C9B—C10B—C13B—O1B17.9 (3)
C2A—C1A—C12A—C7A174.4 (2)C11B—C10B—C13B—N3B19.8 (3)
C11A—C10A—C13A—O1A166.2 (2)C9B—C10B—C13B—N3B161.9 (2)
C9A—C10A—C13A—O1A14.6 (3)C1B—C6B—N1B—C7B0.9 (3)
C11A—C10A—C13A—N3A15.5 (3)C5B—C6B—N1B—C7B179.0 (2)
C9A—C10A—C13A—N3A163.7 (2)C8B—C7B—N1B—C6B178.9 (3)
C1A—C6A—N1A—C7A0.1 (3)C12B—C7B—N1B—C6B1.0 (3)
C5A—C6A—N1A—C7A177.9 (2)C4B—C3B—N2B—C14B160.4 (2)
C8A—C7A—N1A—C6A179.9 (2)C2B—C3B—N2B—C14B75.1 (3)
C12A—C7A—N1A—C6A1.1 (3)O2—C15—C16—C1748.0 (4)
C4A—C3A—N2A—C14A160.9 (2)O3—C15—C16—C17133.8 (3)
C2A—C3A—N2A—C14A75.5 (3)C15—C16—C17—C18177.5 (3)
C6B—C1B—C2B—C3B16.1 (3)C16—C17—C18—O419.2 (4)
C12B—C1B—C2B—C3B167.7 (2)C16—C17—C18—O5162.2 (3)
C1B—C2B—C3B—N2B83.1 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1A—H1N···O2i0.84 (4)2.20 (4)2.976 (3)154 (3)
N1A—H1N···O3i0.84 (4)2.40 (4)3.140 (3)147 (3)
N2A—H2N···O30.85 (3)2.00 (3)2.826 (3)162 (3)
N2A—H3N···O5ii0.87 (3)1.93 (3)2.738 (3)154 (3)
N3A—H4N···O1B0.89 (3)2.06 (4)2.951 (3)173 (3)
N3A—H5N···O50.81 (4)2.60 (4)3.277 (4)142 (3)
N1B—H6N···O4iii0.81 (4)2.23 (4)2.981 (3)153 (3)
N2B—H7N···O2Wiv0.90 (3)1.80 (4)2.687 (3)168 (3)
N2B—H8N···O1Aiv0.86 (3)1.96 (3)2.792 (3)163 (2)
N3B—H9N···O1W0.85 (4)2.36 (4)3.175 (3)160 (3)
N3B—H10N···O1A0.89 (3)2.05 (3)2.930 (3)169 (3)
O1W—H1W···O3v0.81 (4)1.94 (4)2.735 (3)172 (4)
O1W—H2W···O3W0.83 (4)2.01 (4)2.826 (3)167 (3)
O2W—H3W···O1W0.82 (6)1.91 (6)2.729 (3)177 (5)
O2W—H4W···O2vi0.84 (4)1.82 (4)2.661 (4)179 (4)
O3W—H5W···O4vii0.82 (4)1.95 (4)2.749 (3)165 (4)
O3W—H6W···O1Bviii0.89 (5)1.97 (5)2.846 (3)168 (4)
C3A—H3A···O1Bii0.982.543.462 (3)156
Symmetry codes: (i) x1, y+1/2, z+4; (ii) x, y, z+1; (iii) x+1, y, z1; (iv) x, y, z1; (v) x1, y+1/2, z+3; (vi) x, y+1/2, z+3; (vii) x1, y+1/2, z+2; (viii) x, y+1/2, z+2.
Table 1. Selected geometric parameters (Å ,° ) for (I)–(III) top
Parameter(I)(IIA) cation/anion(IIB) cation/anion(III)
C15—O21.244 (2)1.302 (5)1.302 (6)1.232 (3)
C15—O31.257 (2)1.183 (5)1.172 (5)1.254 (3)
C18—O41.225 (5)1.226 (5)1.246 (3)
C18—O51.268 (5)1.264 (5)1.246 (3)
C13—O11.234 (2)1.253 (4)1.250 (4)1.250 (3)/1.248 (3)*
C13—N31.325 (3)1.314 (5)1.320 (5)1.328 (3)/1.330 (3)*
O2—C15—C16118.8 (2)113.2 (3)114.0 (4)119.7 (2)
O3—C15—C16117.8 (2)124.0 (4)124.1 (4)118.3 (2)
O4—C18—C17119.6 (4)119.7 (4)117.9 (2)
O5—C18—C17116.4 (3)116.5 (4)116.0 (2)
O1—C13—N3120.42 (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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