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Two mixed crystals were obtained by crystallizing the active pharmaceutical ingre­dient pyridoxine [systematic name: 4,5-bis­(hy­droxy­meth­yl)-2-methyl­pyri­din-3-ol, PN] with (E)-3-(4-hy­droxy-3-meth­oxy­phen­yl)prop-2-enoic acid (feru­lic acid) and 4-hy­droxy-3,5-di­meth­oxy­benzoic acid (syringic acid). PN and the coformers crystallize in the form of pharmaceutical salts in a 1:1 stoichiometric ratio, namely 3-hy­droxy-4,5-bis­(hy­droxy­meth­yl)-2-methyl­pyridin-1-ium (E)-3-(4-hy­droxy-3-meth­oxy­phen­yl)prop-2-enoate, C8H12NO3+·C9H9O5, and 3-hy­droxy-4,5-bis­(hy­droxy­meth­yl)-2-methyl­pyridin-1-ium 4-hy­droxy-3,5-di­meth­oxy­benzoate monohydrate, C8H12NO3+·C10H11O5·H2O, the proton exchange between PN and the acidic partner being supported by the differences of the pKa values of the two components and by the C—O bond lengths of the carb­oxy­late groups. Besides complex hydrogen-bonding networks, π–π inter­actions between aromatic moieties have been found to be important for the packing architecture in both crystals. Hirshfeld surface analysis was used to explore the inter­molecular inter­actions in detail and compare them with the inter­actions found in similar pyridoxine/carb­oxy­lic acid salts.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S2053229617015765/ku3209sup1.cif
Contains datablocks shelx1, comp2, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2053229617015765/ku3209shelx1sup2.hkl
Contains datablock shelx1

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2053229617015765/ku3209comp2sup3.hkl
Contains datablock comp2

cml

Chemical Markup Language (CML) file https://doi.org/10.1107/S2053229617015765/ku3209shelx1sup4.cml
Supplementary material

cml

Chemical Markup Language (CML) file https://doi.org/10.1107/S2053229617015765/ku3209comp2sup5.cml
Supplementary material

CCDC references: 1582758; 1582757

Computing details top

For both structures, data collection: COLLECT (Nonius, 1997); cell refinement: DENZO-SMN (Otwinowski & Minor, 1997); data reduction: DENZO-SMN (Otwinowski & Minor, 1997); program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015); molecular graphics: ORTEPIII (Burnett & Johnson, 1996) and MarvinSketch (ChemAxon, 2010); software used to prepare material for publication: SHELXL2014 (Sheldrick, 2015) and WinGX (Farrugia, 2012).

3-Hydroxy-4,5-bis(hydroxymethyl)-2-methylpyridin-1-ium 4-hydroxy-3,5-dimethoxybenzoate monohydrate (shelx1) top
Crystal data top
C8H12NO3+·C9H9O5Z = 2
Mr = 367.35F(000) = 388
Triclinic, P1Dx = 1.273 Mg m3
a = 6.9085 (2) ÅMo Kα radiation, λ = 0.71073 Å
b = 8.4524 (2) ÅCell parameters from 18203 reflections
c = 17.9702 (5) Åθ = 3–27°
α = 101.8010 (16)°µ = 0.10 mm1
β = 92.7110 (16)°T = 295 K
γ = 109.8290 (14)°Plate, colourless
V = 958.47 (5) Å30.52 × 0.20 × 0.09 mm
Data collection top
Nonius KappaCCD
diffractometer
Rint = 0.035
φ scans and ω scansθmax = 27.5°, θmin = 3.1°
18203 measured reflectionsh = 88
4387 independent reflectionsk = 1010
3191 reflections with I > 2σ(I)l = 2323
Refinement top
Refinement on F2Hydrogen site location: mixed
Least-squares matrix: fullH atoms treated by a mixture of independent and constrained refinement
R[F2 > 2σ(F2)] = 0.053 w = 1/[σ2(Fo2) + (0.0972P)2 + 0.1657P]
where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.167(Δ/σ)max < 0.001
S = 1.06Δρmax = 0.38 e Å3
4387 reflectionsΔρmin = 0.27 e Å3
256 parametersExtinction correction: SHELXL2014 (Sheldrick, 2015), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
0 restraintsExtinction coefficient: 0.049 (12)
Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
N10.0285 (2)0.59703 (18)0.20164 (8)0.0356 (3)
O10.1171 (3)0.72836 (18)0.00103 (9)0.0750 (6)
O20.2464 (2)1.24197 (14)0.27041 (7)0.0437 (3)
O30.2151 (2)0.99184 (17)0.34344 (7)0.0500 (4)
O40.0942 (2)0.26847 (15)0.21330 (8)0.0491 (4)
O50.2842 (3)0.0993 (2)0.10465 (8)0.0679 (5)
O60.3275 (2)0.10970 (16)0.40501 (7)0.0571 (4)
O70.4868 (2)0.42453 (16)0.32123 (7)0.0503 (4)
O80.5267 (2)0.49958 (15)0.16857 (7)0.0530 (4)
C10.0551 (2)0.6461 (2)0.13492 (10)0.0355 (4)
H10.01870.56300.08880.043*
C20.1360 (3)0.8185 (2)0.13488 (9)0.0352 (4)
C30.1906 (2)0.9421 (2)0.20504 (10)0.0351 (4)
C40.1620 (3)0.8850 (2)0.27271 (10)0.0358 (4)
C50.0775 (3)0.7085 (2)0.27035 (9)0.0358 (4)
C60.1681 (3)0.8730 (2)0.06041 (10)0.0484 (5)
H6A0.08210.93990.05300.058*
H6B0.31180.94600.06220.058*
C70.2845 (3)1.1324 (2)0.20618 (12)0.0475 (5)
H7A0.43321.16390.20610.057*
H7B0.22891.15200.15970.057*
C80.0449 (3)0.6418 (3)0.34144 (11)0.0504 (5)
H8A0.02690.51880.32770.076*
H8B0.03610.69590.37190.076*
H8C0.17690.66800.37040.076*
C90.2191 (3)0.1241 (2)0.17279 (11)0.0406 (4)
C100.2906 (2)0.0230 (2)0.21191 (9)0.0344 (4)
C110.3779 (3)0.1917 (2)0.16787 (9)0.0359 (4)
H110.39380.21340.11470.043*
C120.4411 (3)0.3270 (2)0.20417 (9)0.0352 (4)
C130.4236 (3)0.2945 (2)0.28378 (9)0.0361 (4)
C140.3377 (3)0.1254 (2)0.32759 (9)0.0374 (4)
C150.2698 (3)0.0107 (2)0.29161 (10)0.0368 (4)
H150.21060.12390.32060.044*
C160.5400 (4)0.5445 (3)0.08700 (11)0.0617 (6)
H16A0.45070.44820.06970.093*
H16B0.68050.57340.06500.093*
H16C0.49780.64220.07150.093*
C170.2404 (5)0.0579 (3)0.45295 (13)0.0834 (9)
H17A0.12170.12450.43260.125*
H17B0.19860.05040.50340.125*
H17C0.34150.11300.45540.125*
H1O0.155 (4)0.770 (4)0.0395 (17)0.080 (8)*
H2O0.123 (5)1.243 (4)0.2578 (18)0.097 (10)*
H3O0.252 (5)1.108 (4)0.3378 (18)0.102 (10)*
H1N0.019 (3)0.482 (3)0.2007 (11)0.046 (5)*
H7O0.554 (4)0.525 (4)0.2870 (16)0.074 (8)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N10.0409 (7)0.0255 (7)0.0409 (8)0.0094 (6)0.0070 (6)0.0128 (6)
O10.1270 (15)0.0346 (7)0.0400 (8)0.0016 (8)0.0173 (9)0.0095 (6)
O20.0503 (8)0.0241 (6)0.0490 (7)0.0076 (5)0.0025 (6)0.0024 (5)
O30.0740 (9)0.0329 (7)0.0379 (7)0.0146 (6)0.0051 (6)0.0049 (5)
O40.0563 (8)0.0271 (6)0.0626 (8)0.0084 (5)0.0065 (6)0.0191 (6)
O50.0870 (11)0.0577 (9)0.0480 (8)0.0022 (8)0.0044 (7)0.0303 (7)
O60.0896 (11)0.0348 (7)0.0301 (6)0.0022 (7)0.0041 (6)0.0066 (5)
O70.0725 (9)0.0283 (6)0.0394 (7)0.0005 (6)0.0056 (6)0.0150 (5)
O80.0810 (10)0.0268 (6)0.0364 (7)0.0030 (6)0.0077 (6)0.0035 (5)
C10.0388 (8)0.0284 (8)0.0376 (8)0.0086 (6)0.0059 (7)0.0095 (6)
C20.0376 (8)0.0292 (8)0.0393 (9)0.0105 (6)0.0070 (7)0.0113 (7)
C30.0383 (8)0.0251 (7)0.0432 (9)0.0111 (6)0.0095 (7)0.0104 (6)
C40.0428 (8)0.0277 (8)0.0369 (8)0.0132 (7)0.0048 (7)0.0070 (6)
C50.0427 (9)0.0293 (8)0.0374 (8)0.0133 (7)0.0056 (7)0.0116 (6)
C60.0672 (12)0.0320 (9)0.0423 (10)0.0094 (8)0.0113 (9)0.0136 (7)
C70.0585 (11)0.0251 (8)0.0588 (11)0.0121 (8)0.0202 (9)0.0117 (8)
C80.0719 (13)0.0418 (10)0.0416 (10)0.0195 (9)0.0106 (9)0.0194 (8)
C90.0429 (9)0.0353 (9)0.0478 (10)0.0123 (7)0.0134 (7)0.0199 (7)
C100.0348 (8)0.0288 (8)0.0399 (9)0.0082 (6)0.0070 (6)0.0134 (6)
C110.0401 (8)0.0332 (8)0.0328 (8)0.0086 (7)0.0073 (6)0.0112 (6)
C120.0390 (8)0.0272 (8)0.0339 (8)0.0050 (6)0.0041 (6)0.0070 (6)
C130.0416 (8)0.0266 (8)0.0365 (8)0.0052 (6)0.0057 (7)0.0115 (7)
C140.0451 (9)0.0303 (8)0.0312 (8)0.0058 (7)0.0048 (7)0.0083 (6)
C150.0411 (8)0.0242 (7)0.0400 (9)0.0049 (6)0.0055 (7)0.0082 (6)
C160.0843 (15)0.0441 (11)0.0381 (10)0.0057 (10)0.0084 (10)0.0012 (8)
C170.136 (2)0.0461 (12)0.0380 (11)0.0031 (14)0.0042 (13)0.0030 (9)
Geometric parameters (Å, º) top
N1—C51.340 (2)C5—C81.495 (2)
N1—C11.347 (2)C6—H6A0.9700
N1—H1N0.91 (2)C6—H6B0.9700
O1—C61.399 (2)C7—H7A0.9700
O1—H1O0.85 (3)C7—H7B0.9700
O2—C71.420 (2)C8—H8A0.9600
O2—H2O0.87 (3)C8—H8B0.9600
O3—C41.352 (2)C8—H8C0.9600
O3—H3O0.95 (3)C9—C101.503 (2)
O4—C91.275 (2)C10—C111.390 (2)
O5—C91.235 (2)C10—C151.393 (2)
O6—C141.366 (2)C11—C121.385 (2)
O6—C171.409 (2)C11—H110.9300
O7—C131.3626 (19)C12—C131.392 (2)
O7—H7O0.90 (3)C13—C141.391 (2)
O8—C121.3727 (19)C14—C151.389 (2)
O8—C161.427 (2)C15—H150.9300
C1—C21.372 (2)C16—H16A0.9600
C1—H10.9300C16—H16B0.9600
C2—C31.405 (2)C16—H16C0.9600
C2—C61.505 (2)C17—H17A0.9600
C3—C41.396 (2)C17—H17B0.9600
C3—C71.512 (2)C17—H17C0.9600
C4—C51.396 (2)
C5—N1—C1123.59 (14)H8A—C8—H8B109.5
C5—N1—H1N117.5 (13)C5—C8—H8C109.5
C1—N1—H1N118.8 (13)H8A—C8—H8C109.5
C6—O1—H1O104.7 (19)H8B—C8—H8C109.5
C7—O2—H2O105 (2)O5—C9—O4124.23 (16)
C4—O3—H3O108.1 (19)O5—C9—C10118.93 (16)
C14—O6—C17117.84 (15)O4—C9—C10116.84 (16)
C13—O7—H7O109.3 (17)C11—C10—C15120.72 (14)
C12—O8—C16117.14 (14)C11—C10—C9119.43 (15)
N1—C1—C2120.10 (15)C15—C10—C9119.85 (15)
N1—C1—H1120.0C12—C11—C10119.23 (15)
C2—C1—H1120.0C12—C11—H11120.4
C1—C2—C3119.16 (15)C10—C11—H11120.4
C1—C2—C6120.06 (15)O8—C12—C11125.88 (15)
C3—C2—C6120.77 (14)O8—C12—C13113.64 (14)
C4—C3—C2118.66 (14)C11—C12—C13120.47 (15)
C4—C3—C7121.44 (15)O7—C13—C14118.00 (15)
C2—C3—C7119.87 (15)O7—C13—C12121.94 (15)
O3—C4—C5115.73 (15)C14—C13—C12120.06 (14)
O3—C4—C3123.78 (15)O6—C14—C15125.48 (15)
C5—C4—C3120.48 (15)O6—C14—C13114.76 (14)
N1—C5—C4118.00 (15)C15—C14—C13119.77 (15)
N1—C5—C8119.78 (14)C14—C15—C10119.72 (15)
C4—C5—C8122.21 (15)C14—C15—H15120.1
O1—C6—C2110.61 (14)C10—C15—H15120.1
O1—C6—H6A109.5O8—C16—H16A109.5
C2—C6—H6A109.5O8—C16—H16B109.5
O1—C6—H6B109.5H16A—C16—H16B109.5
C2—C6—H6B109.5O8—C16—H16C109.5
H6A—C6—H6B108.1H16A—C16—H16C109.5
O2—C7—C3113.71 (14)H16B—C16—H16C109.5
O2—C7—H7A108.8O6—C17—H17A109.5
C3—C7—H7A108.8O6—C17—H17B109.5
O2—C7—H7B108.8H17A—C17—H17B109.5
C3—C7—H7B108.8O6—C17—H17C109.5
H7A—C7—H7B107.7H17A—C17—H17C109.5
C5—C8—H8A109.5H17B—C17—H17C109.5
C5—C8—H8B109.5
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1N···O40.91 (2)1.77 (2)2.671 (2)171 (2)
O3—H3O···O20.95 (4)1.83 (4)2.663 (2)144 (3)
C8—H8A···O40.962.523.308 (2)139
C1—H1···O1i0.932.473.359 (2)158
O1—H1O···O5i0.85 (3)1.83 (3)2.663 (2)166 (3)
C6—H6B···O5ii0.972.643.576 (3)161
O2—H2O···O4iii0.87 (4)1.77 (4)2.620 (2)165 (3)
O7—H7O···O2iv0.89 (2)1.93 (2)2.728 (1)146 (3)
Symmetry codes: (i) x, y+1, z; (ii) x+1, y+1, z; (iii) x, y+1, z; (iv) x1, y2, z.
3-Hydroxy-4,5-bis(hydroxymethyl)-2-methylpyridin-1-ium (E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoate monohydrate (comp2) top
Crystal data top
C8H12NO3+·C10H11O5·H2OF(000) = 404
Mr = 381.37Dx = 1.418 Mg m3
Monoclinic, P21Mo Kα radiation, λ = 0.71073 Å
a = 7.2440 (3) ÅCell parameters from 11173 reflections
b = 17.1615 (5) Åθ = 4–30°
c = 7.2706 (2) ŵ = 0.11 mm1
β = 98.806 (2)°T = 295 K
V = 893.21 (5) Å3Prismatic, colourless
Z = 20.35 × 0.22 × 0.13 mm
Data collection top
Nonius Kappa CCD
diffractometer
Rint = 0.034
φ scans and ω scansθmax = 30.0°, θmin = 4.5°
11173 measured reflectionsh = 109
4578 independent reflectionsk = 2422
3822 reflections with I > 2σ(I)l = 1010
Refinement top
Refinement on F2Hydrogen site location: mixed
Least-squares matrix: fullH atoms treated by a mixture of independent and constrained refinement
R[F2 > 2σ(F2)] = 0.040 w = 1/[σ2(Fo2) + (0.063P)2 + 0.0278P]
where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.108(Δ/σ)max < 0.001
S = 1.07Δρmax = 0.27 e Å3
4578 reflectionsΔρmin = 0.18 e Å3
272 parametersAbsolute structure: Flack x determined using 1452 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons et al., 2013)
1 restraintAbsolute structure parameter: 0.4 (4)
Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
N10.8860 (3)0.19960 (10)1.1832 (2)0.0354 (4)
O10.7016 (3)0.39465 (12)0.8941 (2)0.0551 (5)
O20.9773 (4)0.40722 (13)1.6750 (3)0.0622 (6)
O31.0560 (3)0.26271 (12)1.6424 (2)0.0526 (4)
O40.7236 (2)0.12996 (9)0.7844 (2)0.0457 (4)
O50.8366 (3)0.05993 (9)1.0310 (2)0.0473 (4)
O60.4671 (3)0.36773 (9)0.5400 (2)0.0492 (4)
O70.6240 (3)0.35956 (10)0.8823 (2)0.0565 (5)
O1W0.5731 (3)0.00760 (11)1.2468 (2)0.0502 (4)
C10.8257 (3)0.26552 (12)1.0932 (3)0.0352 (4)
H10.77600.26350.96750.042*
C20.8367 (3)0.33573 (12)1.1852 (3)0.0325 (4)
C30.9116 (3)0.33702 (12)1.3759 (3)0.0331 (4)
C40.9767 (3)0.26757 (13)1.4613 (3)0.0356 (4)
C50.9623 (3)0.19785 (12)1.3625 (3)0.0352 (4)
C60.7702 (3)0.40987 (12)1.0846 (3)0.0384 (4)
H6A0.87270.44671.09340.046*
H6B0.67190.43301.14340.046*
C70.9194 (4)0.41369 (14)1.4799 (3)0.0466 (5)
H7A0.79650.43741.45800.056*
H7B1.00470.44831.42910.056*
C81.0285 (4)0.12139 (15)1.4478 (3)0.0464 (5)
H8A1.00560.08101.35570.070*
H8B1.15990.12431.49310.070*
H8C0.96220.10981.54920.070*
C90.7545 (3)0.06564 (11)0.8646 (3)0.0332 (4)
C100.6902 (3)0.00681 (12)0.7617 (3)0.0368 (4)
H100.63180.00270.63900.044*
C110.7130 (3)0.07718 (12)0.8386 (3)0.0332 (4)
H110.77540.07930.96020.040*
C120.6508 (3)0.15162 (11)0.7528 (3)0.0320 (4)
C130.6705 (3)0.21921 (12)0.8628 (3)0.0349 (4)
H130.72480.21590.98710.042*
C140.6101 (3)0.29043 (12)0.7888 (3)0.0365 (4)
C150.5249 (3)0.29579 (12)0.6022 (3)0.0363 (4)
C160.5067 (3)0.22952 (12)0.4926 (3)0.0370 (4)
H160.45180.23300.36860.044*
C170.5697 (3)0.15779 (12)0.5661 (3)0.0365 (4)
H170.55780.11370.49070.044*
C180.7096 (4)0.35938 (16)1.0716 (3)0.0537 (6)
H18A0.64400.32411.14110.081*
H18B0.70530.41091.12210.081*
H18C0.83730.34301.07970.081*
H1N0.879 (5)0.153 (3)1.116 (5)0.080 (11)*
H1O0.614 (4)0.428 (2)0.855 (4)0.046 (7)*
H2O0.877 (8)0.403 (3)1.737 (7)0.115 (18)*
H3O1.038 (6)0.313 (3)1.674 (6)0.081 (12)*
H6O0.396 (5)0.360 (3)0.422 (6)0.080 (11)*
H1W0.537 (6)0.035 (3)1.282 (6)0.078 (11)*
H2W0.674 (7)0.007 (3)1.196 (6)0.100 (14)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N10.0409 (9)0.0269 (8)0.0361 (8)0.0026 (7)0.0010 (7)0.0031 (7)
O10.0745 (13)0.0494 (10)0.0396 (9)0.0207 (10)0.0032 (8)0.0049 (8)
O20.0801 (14)0.0624 (13)0.0422 (9)0.0019 (11)0.0025 (9)0.0191 (9)
O30.0712 (12)0.0515 (10)0.0313 (7)0.0014 (9)0.0048 (7)0.0008 (7)
O40.0667 (10)0.0267 (7)0.0392 (8)0.0019 (7)0.0061 (7)0.0014 (6)
O50.0688 (11)0.0296 (7)0.0376 (8)0.0047 (7)0.0103 (7)0.0000 (6)
O60.0712 (11)0.0276 (8)0.0419 (8)0.0069 (8)0.0129 (7)0.0032 (6)
O70.0924 (13)0.0285 (8)0.0404 (8)0.0096 (9)0.0163 (8)0.0027 (7)
O1W0.0700 (12)0.0332 (8)0.0473 (9)0.0067 (8)0.0082 (8)0.0033 (7)
C10.0406 (10)0.0300 (9)0.0333 (9)0.0005 (9)0.0001 (8)0.0016 (8)
C20.0336 (10)0.0292 (9)0.0345 (9)0.0019 (8)0.0047 (7)0.0000 (8)
C30.0360 (10)0.0309 (9)0.0330 (9)0.0039 (8)0.0079 (7)0.0029 (8)
C40.0398 (10)0.0366 (10)0.0296 (9)0.0051 (9)0.0030 (7)0.0021 (8)
C50.0368 (10)0.0331 (10)0.0348 (9)0.0010 (9)0.0021 (8)0.0023 (8)
C60.0443 (11)0.0310 (10)0.0399 (10)0.0038 (9)0.0066 (8)0.0031 (8)
C70.0655 (15)0.0356 (11)0.0404 (11)0.0078 (11)0.0135 (10)0.0098 (9)
C80.0552 (13)0.0369 (11)0.0440 (11)0.0023 (10)0.0017 (9)0.0060 (9)
C90.0392 (10)0.0262 (9)0.0333 (9)0.0041 (8)0.0025 (7)0.0028 (7)
C100.0450 (11)0.0296 (9)0.0333 (9)0.0015 (9)0.0017 (8)0.0030 (8)
C110.0349 (10)0.0289 (9)0.0347 (9)0.0010 (8)0.0020 (7)0.0036 (8)
C120.0331 (10)0.0255 (9)0.0365 (9)0.0000 (8)0.0022 (7)0.0032 (8)
C130.0405 (10)0.0296 (10)0.0323 (9)0.0009 (8)0.0017 (7)0.0020 (8)
C140.0426 (11)0.0280 (10)0.0366 (10)0.0003 (9)0.0014 (8)0.0014 (8)
C150.0414 (11)0.0293 (9)0.0360 (10)0.0020 (9)0.0005 (8)0.0059 (8)
C160.0438 (11)0.0312 (9)0.0333 (9)0.0003 (9)0.0030 (8)0.0031 (8)
C170.0431 (11)0.0293 (9)0.0354 (9)0.0000 (9)0.0009 (8)0.0006 (8)
C180.0772 (17)0.0407 (12)0.0377 (11)0.0052 (12)0.0088 (11)0.0075 (10)
Geometric parameters (Å, º) top
N1—C51.336 (3)C6—H6A0.9700
N1—C11.346 (3)C6—H6B0.9700
N1—H1N0.93 (5)C7—H7A0.9700
O1—C61.423 (3)C7—H7B0.9700
O1—H1O0.87 (3)C8—H8A0.9600
O2—C71.421 (3)C8—H8B0.9600
O2—H2O0.92 (5)C8—H8C0.9600
O3—C41.356 (2)C9—C101.488 (3)
O3—H3O0.91 (5)C10—C111.330 (3)
O4—C91.253 (3)C10—H100.9300
O5—C91.267 (3)C11—C121.462 (3)
O6—C151.359 (3)C11—H110.9300
O6—H6O0.94 (4)C12—C171.398 (3)
O7—C141.363 (3)C12—C131.404 (3)
O7—C181.421 (3)C13—C141.379 (3)
O1W—H1W0.82 (5)C13—H130.9300
O1W—H2W0.90 (5)C14—C151.405 (3)
C1—C21.374 (3)C15—C161.383 (3)
C1—H10.9300C16—C171.391 (3)
C2—C31.409 (3)C16—H160.9300
C2—C61.509 (3)C17—H170.9300
C3—C41.393 (3)C18—H18A0.9600
C3—C71.514 (3)C18—H18B0.9600
C4—C51.391 (3)C18—H18C0.9600
C5—C81.498 (3)
C5—N1—C1123.26 (18)H8A—C8—H8B109.5
C5—N1—H1N118 (2)C5—C8—H8C109.5
C1—N1—H1N118 (2)H8A—C8—H8C109.5
C6—O1—H1O109.4 (19)H8B—C8—H8C109.5
C7—O2—H2O111 (3)O4—C9—O5122.47 (18)
C4—O3—H3O98 (3)O4—C9—C10118.83 (17)
C15—O6—H6O106 (3)O5—C9—C10118.69 (17)
C14—O7—C18117.98 (18)C11—C10—C9122.54 (17)
H1W—O1W—H2W102 (4)C11—C10—H10118.7
N1—C1—C2120.66 (18)C9—C10—H10118.7
N1—C1—H1119.7C10—C11—C12127.11 (18)
C2—C1—H1119.7C10—C11—H11116.4
C1—C2—C3118.51 (19)C12—C11—H11116.4
C1—C2—C6120.87 (18)C17—C12—C13118.80 (18)
C3—C2—C6120.62 (18)C17—C12—C11122.46 (18)
C4—C3—C2118.58 (18)C13—C12—C11118.73 (17)
C4—C3—C7122.45 (18)C14—C13—C12120.74 (18)
C2—C3—C7118.97 (19)C14—C13—H13119.6
O3—C4—C5115.8 (2)C12—C13—H13119.6
O3—C4—C3123.4 (2)O7—C14—C13125.58 (18)
C5—C4—C3120.81 (17)O7—C14—C15114.36 (18)
N1—C5—C4118.13 (18)C13—C14—C15120.06 (18)
N1—C5—C8118.81 (19)O6—C15—C16123.92 (18)
C4—C5—C8123.06 (18)O6—C15—C14116.62 (19)
O1—C6—C2110.78 (17)C16—C15—C14119.45 (18)
O1—C6—H6A109.5C15—C16—C17120.63 (19)
C2—C6—H6A109.5C15—C16—H16119.7
O1—C6—H6B109.5C17—C16—H16119.7
C2—C6—H6B109.5C16—C17—C12120.29 (19)
H6A—C6—H6B108.1C16—C17—H17119.9
O2—C7—C3114.4 (2)C12—C17—H17119.9
O2—C7—H7A108.7O7—C18—H18A109.5
C3—C7—H7A108.7O7—C18—H18B109.5
O2—C7—H7B108.7H18A—C18—H18B109.5
C3—C7—H7B108.7O7—C18—H18C109.5
H7A—C7—H7B107.6H18A—C18—H18C109.5
C5—C8—H8A109.5H18B—C18—H18C109.5
C5—C8—H8B109.5
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1N···O50.93 (4)1.73 (5)2.641 (2)166 (4)
O3—H3O···O20.90 (5)1.68 (5)2.564 (3)165 (4)
O1W—H2W···O50.90 (5)2.02 (5)2.893 (3)161 (5)
C8—H8A···O50.962.513.307 (3)140
O2—H2O···O1i0.91 (6)1.84 (6)2.747 (3)171 (5)
C8—H8C···O4i0.962.633.541 (3)158
C17—H17···O1Wii0.932.553.472 (3)167
O6—H6O···O4iii0.94 (4)1.62 (4)2.545 (2)166 (4)
O1—H1O···O1Wiv0.86 (3)1.82 (3)2.683 (3)175 (3)
O1W—H1W···O6iviv0.82 (5)2.12 (5)2.896 (2)156 (4)
O1W—H1W···O7iviv0.82 (5)2.37 (5)2.994 (3)132 (4)
Symmetry codes: (i) x, y, z+1; (ii) x, y, z1; (iii) x+1, y+1/2, z+1; (iv) x+1, y1/2, z+2.
Structural parameters for hydrogen bonds and ππ interactions (Å, °) for (1) and (2) top
Cg represents a ring centroid.
D—H···AD—HD···AH···AD—H···A
Cocrystal (1)
N1—H1N···O40.91 (2)2.671 (2)1.77 (2)171 (2)
O3—H3O···O20.95 (4)2.663 (2)1.83 (4)144 (3)
C8—H8A···O40.963.308 (2)2.52139
C1—H1···O1i0.933.359 (2)2.47158
O1—H1O···O5i0.85 (3)2.663 (2)1.83 (3)166 (3)
C6—H6B···O5ii0.973.576 (3)2.64161
O2—H2O···O4iii0.87 (4)2.620 (2)1.77 (4)165 (3)
O7—H7O···O2iv0.89 (2)2.728 (1)1.93 (2)146 (3)
ππ interactions
Cg(C10–C15···Cg(N1/C1–C5)v3.552
Cg(C10–C15)···Cg(N1/C1–C5)vi3.577
Cocrystal (2)
N1—H1N···O50.93 (4)2.641 (2)1.73 (5)166 (4)
O3—H3O···O20.90 (5)2.564 (3)1.68 (5)165 (4)
O1W–H2W···O50.90 (5)2.893 (3)2.02 (5)161 (5)
C8—H8A···O50.963.307 (3)2.51140
O2—H2O···O1vii0.91 (6)2.747 (3)1.84 (6)171 (5)
C8—H8C···O4vii0.963.541 (3)2.63158
C17—H17···O1Wviii0.933.472 (3)2.55167
O6—H6O···O4ix0.94 (4)2.545 (2)1.62 (4)166 (4)
O1—H1O···O1Wx0.86 (3)2.683 (3)1.82 (3)175 (3)
O1W—H1W···O6x0.82 (5)2.896 (2)2.12 (5)156 (4)
O1W—H1W···O7x0.82 (5)2.994 (3)2.37 (5)132 (4)
ππ interactions
Cg(C12–C17)···Cg(N1/C1–C5)xi3.608
Cg(C12–C17)···Cg(N1/C1–C5)xii3.671
Symmetry codes: (i) -x, -y+1, -z; (ii) x+1, y+1, z; (iii) x, y+1, z; (iv) x-1, y-2, z; (v) x-1, y-1, z; (vi) x, y-1, z; (vii) x, y, z+1; (viii) x, y, z-1; (ix) -x+1, y+1/2, -z+1; (x) -x+1, y-1/2, -z+2; (xi) -x+1, y+1/2, -z+2; (xii) -x+2, y+1/2, -z+2.
 

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