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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
CCDC references: 1582758; 1582757
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+·C9H9O5− | Z = 2 |
Mr = 367.35 | F(000) = 388 |
Triclinic, P1 | Dx = 1.273 Mg m−3 |
a = 6.9085 (2) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 8.4524 (2) Å | Cell parameters from 18203 reflections |
c = 17.9702 (5) Å | θ = 3–27° |
α = 101.8010 (16)° | µ = 0.10 mm−1 |
β = 92.7110 (16)° | T = 295 K |
γ = 109.8290 (14)° | Plate, colourless |
V = 958.47 (5) Å3 | 0.52 × 0.20 × 0.09 mm |
Data collection top
Nonius KappaCCD diffractometer | Rint = 0.035 |
φ scans and ω scans | θmax = 27.5°, θmin = 3.1° |
18203 measured reflections | h = −8→8 |
4387 independent reflections | k = −10→10 |
3191 reflections with I > 2σ(I) | l = −23→23 |
Refinement top
Refinement on F2 | Hydrogen site location: mixed |
Least-squares matrix: full | H 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 = 1.06 | Δρmax = 0.38 e Å−3 |
4387 reflections | Δρmin = −0.27 e Å−3 |
256 parameters | Extinction correction: SHELXL2014 (Sheldrick, 2015), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
0 restraints | Extinction 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 | x | y | z | Uiso*/Ueq | |
N1 | 0.0285 (2) | 0.59703 (18) | 0.20164 (8) | 0.0356 (3) | |
O1 | 0.1171 (3) | 0.72836 (18) | −0.00103 (9) | 0.0750 (6) | |
O2 | 0.2464 (2) | 1.24197 (14) | 0.27041 (7) | 0.0437 (3) | |
O3 | 0.2151 (2) | 0.99184 (17) | 0.34344 (7) | 0.0500 (4) | |
O4 | −0.0942 (2) | 0.26847 (15) | 0.21330 (8) | 0.0491 (4) | |
O5 | −0.2842 (3) | 0.0993 (2) | 0.10465 (8) | 0.0679 (5) | |
O6 | −0.3275 (2) | −0.10970 (16) | 0.40501 (7) | 0.0571 (4) | |
O7 | −0.4868 (2) | −0.42453 (16) | 0.32123 (7) | 0.0503 (4) | |
O8 | −0.5267 (2) | −0.49958 (15) | 0.16857 (7) | 0.0530 (4) | |
C1 | 0.0551 (2) | 0.6461 (2) | 0.13492 (10) | 0.0355 (4) | |
H1 | 0.0187 | 0.5630 | 0.0888 | 0.043* | |
C2 | 0.1360 (3) | 0.8185 (2) | 0.13488 (9) | 0.0352 (4) | |
C3 | 0.1906 (2) | 0.9421 (2) | 0.20504 (10) | 0.0351 (4) | |
C4 | 0.1620 (3) | 0.8850 (2) | 0.27271 (10) | 0.0358 (4) | |
C5 | 0.0775 (3) | 0.7085 (2) | 0.27035 (9) | 0.0358 (4) | |
C6 | 0.1681 (3) | 0.8730 (2) | 0.06041 (10) | 0.0484 (5) | |
H6A | 0.0821 | 0.9399 | 0.0530 | 0.058* | |
H6B | 0.3118 | 0.9460 | 0.0622 | 0.058* | |
C7 | 0.2845 (3) | 1.1324 (2) | 0.20618 (12) | 0.0475 (5) | |
H7A | 0.4332 | 1.1639 | 0.2061 | 0.057* | |
H7B | 0.2289 | 1.1520 | 0.1597 | 0.057* | |
C8 | 0.0449 (3) | 0.6418 (3) | 0.34144 (11) | 0.0504 (5) | |
H8A | −0.0269 | 0.5188 | 0.3277 | 0.076* | |
H8B | −0.0361 | 0.6959 | 0.3719 | 0.076* | |
H8C | 0.1769 | 0.6680 | 0.3704 | 0.076* | |
C9 | −0.2191 (3) | 0.1241 (2) | 0.17279 (11) | 0.0406 (4) | |
C10 | −0.2906 (2) | −0.0230 (2) | 0.21191 (9) | 0.0344 (4) | |
C11 | −0.3779 (3) | −0.1917 (2) | 0.16787 (9) | 0.0359 (4) | |
H11 | −0.3938 | −0.2134 | 0.1147 | 0.043* | |
C12 | −0.4411 (3) | −0.3270 (2) | 0.20417 (9) | 0.0352 (4) | |
C13 | −0.4236 (3) | −0.2945 (2) | 0.28378 (9) | 0.0361 (4) | |
C14 | −0.3377 (3) | −0.1254 (2) | 0.32759 (9) | 0.0374 (4) | |
C15 | −0.2698 (3) | 0.0107 (2) | 0.29161 (10) | 0.0368 (4) | |
H15 | −0.2106 | 0.1239 | 0.3206 | 0.044* | |
C16 | −0.5400 (4) | −0.5445 (3) | 0.08700 (11) | 0.0617 (6) | |
H16A | −0.4507 | −0.4482 | 0.0697 | 0.093* | |
H16B | −0.6805 | −0.5734 | 0.0650 | 0.093* | |
H16C | −0.4978 | −0.6422 | 0.0715 | 0.093* | |
C17 | −0.2404 (5) | 0.0579 (3) | 0.45295 (13) | 0.0834 (9) | |
H17A | −0.1217 | 0.1245 | 0.4326 | 0.125* | |
H17B | −0.1986 | 0.0504 | 0.5034 | 0.125* | |
H17C | −0.3415 | 0.1130 | 0.4554 | 0.125* | |
H1O | 0.155 (4) | 0.770 (4) | −0.0395 (17) | 0.080 (8)* | |
H2O | 0.123 (5) | 1.243 (4) | 0.2578 (18) | 0.097 (10)* | |
H3O | 0.252 (5) | 1.108 (4) | 0.3378 (18) | 0.102 (10)* | |
H1N | −0.019 (3) | 0.482 (3) | 0.2007 (11) | 0.046 (5)* | |
H7O | −0.554 (4) | −0.525 (4) | 0.2870 (16) | 0.074 (8)* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
N1 | 0.0409 (7) | 0.0255 (7) | 0.0409 (8) | 0.0094 (6) | 0.0070 (6) | 0.0128 (6) |
O1 | 0.1270 (15) | 0.0346 (7) | 0.0400 (8) | −0.0016 (8) | 0.0173 (9) | 0.0095 (6) |
O2 | 0.0503 (8) | 0.0241 (6) | 0.0490 (7) | 0.0076 (5) | 0.0025 (6) | 0.0024 (5) |
O3 | 0.0740 (9) | 0.0329 (7) | 0.0379 (7) | 0.0146 (6) | 0.0051 (6) | 0.0049 (5) |
O4 | 0.0563 (8) | 0.0271 (6) | 0.0626 (8) | 0.0084 (5) | 0.0065 (6) | 0.0191 (6) |
O5 | 0.0870 (11) | 0.0577 (9) | 0.0480 (8) | 0.0022 (8) | 0.0044 (7) | 0.0303 (7) |
O6 | 0.0896 (11) | 0.0348 (7) | 0.0301 (6) | 0.0022 (7) | 0.0041 (6) | 0.0066 (5) |
O7 | 0.0725 (9) | 0.0283 (6) | 0.0394 (7) | 0.0005 (6) | 0.0056 (6) | 0.0150 (5) |
O8 | 0.0810 (10) | 0.0268 (6) | 0.0364 (7) | 0.0030 (6) | 0.0077 (6) | 0.0035 (5) |
C1 | 0.0388 (8) | 0.0284 (8) | 0.0376 (8) | 0.0086 (6) | 0.0059 (7) | 0.0095 (6) |
C2 | 0.0376 (8) | 0.0292 (8) | 0.0393 (9) | 0.0105 (6) | 0.0070 (7) | 0.0113 (7) |
C3 | 0.0383 (8) | 0.0251 (7) | 0.0432 (9) | 0.0111 (6) | 0.0095 (7) | 0.0104 (6) |
C4 | 0.0428 (8) | 0.0277 (8) | 0.0369 (8) | 0.0132 (7) | 0.0048 (7) | 0.0070 (6) |
C5 | 0.0427 (9) | 0.0293 (8) | 0.0374 (8) | 0.0133 (7) | 0.0056 (7) | 0.0116 (6) |
C6 | 0.0672 (12) | 0.0320 (9) | 0.0423 (10) | 0.0094 (8) | 0.0113 (9) | 0.0136 (7) |
C7 | 0.0585 (11) | 0.0251 (8) | 0.0588 (11) | 0.0121 (8) | 0.0202 (9) | 0.0117 (8) |
C8 | 0.0719 (13) | 0.0418 (10) | 0.0416 (10) | 0.0195 (9) | 0.0106 (9) | 0.0194 (8) |
C9 | 0.0429 (9) | 0.0353 (9) | 0.0478 (10) | 0.0123 (7) | 0.0134 (7) | 0.0199 (7) |
C10 | 0.0348 (8) | 0.0288 (8) | 0.0399 (9) | 0.0082 (6) | 0.0070 (6) | 0.0134 (6) |
C11 | 0.0401 (8) | 0.0332 (8) | 0.0328 (8) | 0.0086 (7) | 0.0073 (6) | 0.0112 (6) |
C12 | 0.0390 (8) | 0.0272 (8) | 0.0339 (8) | 0.0050 (6) | 0.0041 (6) | 0.0070 (6) |
C13 | 0.0416 (8) | 0.0266 (8) | 0.0365 (8) | 0.0052 (6) | 0.0057 (7) | 0.0115 (7) |
C14 | 0.0451 (9) | 0.0303 (8) | 0.0312 (8) | 0.0058 (7) | 0.0048 (7) | 0.0083 (6) |
C15 | 0.0411 (8) | 0.0242 (7) | 0.0400 (9) | 0.0049 (6) | 0.0055 (7) | 0.0082 (6) |
C16 | 0.0843 (15) | 0.0441 (11) | 0.0381 (10) | 0.0057 (10) | 0.0084 (10) | −0.0012 (8) |
C17 | 0.136 (2) | 0.0461 (12) | 0.0380 (11) | 0.0031 (14) | 0.0042 (13) | −0.0030 (9) |
Geometric parameters (Å, º) top
N1—C5 | 1.340 (2) | C5—C8 | 1.495 (2) |
N1—C1 | 1.347 (2) | C6—H6A | 0.9700 |
N1—H1N | 0.91 (2) | C6—H6B | 0.9700 |
O1—C6 | 1.399 (2) | C7—H7A | 0.9700 |
O1—H1O | 0.85 (3) | C7—H7B | 0.9700 |
O2—C7 | 1.420 (2) | C8—H8A | 0.9600 |
O2—H2O | 0.87 (3) | C8—H8B | 0.9600 |
O3—C4 | 1.352 (2) | C8—H8C | 0.9600 |
O3—H3O | 0.95 (3) | C9—C10 | 1.503 (2) |
O4—C9 | 1.275 (2) | C10—C11 | 1.390 (2) |
O5—C9 | 1.235 (2) | C10—C15 | 1.393 (2) |
O6—C14 | 1.366 (2) | C11—C12 | 1.385 (2) |
O6—C17 | 1.409 (2) | C11—H11 | 0.9300 |
O7—C13 | 1.3626 (19) | C12—C13 | 1.392 (2) |
O7—H7O | 0.90 (3) | C13—C14 | 1.391 (2) |
O8—C12 | 1.3727 (19) | C14—C15 | 1.389 (2) |
O8—C16 | 1.427 (2) | C15—H15 | 0.9300 |
C1—C2 | 1.372 (2) | C16—H16A | 0.9600 |
C1—H1 | 0.9300 | C16—H16B | 0.9600 |
C2—C3 | 1.405 (2) | C16—H16C | 0.9600 |
C2—C6 | 1.505 (2) | C17—H17A | 0.9600 |
C3—C4 | 1.396 (2) | C17—H17B | 0.9600 |
C3—C7 | 1.512 (2) | C17—H17C | 0.9600 |
C4—C5 | 1.396 (2) | | |
| | | |
C5—N1—C1 | 123.59 (14) | H8A—C8—H8B | 109.5 |
C5—N1—H1N | 117.5 (13) | C5—C8—H8C | 109.5 |
C1—N1—H1N | 118.8 (13) | H8A—C8—H8C | 109.5 |
C6—O1—H1O | 104.7 (19) | H8B—C8—H8C | 109.5 |
C7—O2—H2O | 105 (2) | O5—C9—O4 | 124.23 (16) |
C4—O3—H3O | 108.1 (19) | O5—C9—C10 | 118.93 (16) |
C14—O6—C17 | 117.84 (15) | O4—C9—C10 | 116.84 (16) |
C13—O7—H7O | 109.3 (17) | C11—C10—C15 | 120.72 (14) |
C12—O8—C16 | 117.14 (14) | C11—C10—C9 | 119.43 (15) |
N1—C1—C2 | 120.10 (15) | C15—C10—C9 | 119.85 (15) |
N1—C1—H1 | 120.0 | C12—C11—C10 | 119.23 (15) |
C2—C1—H1 | 120.0 | C12—C11—H11 | 120.4 |
C1—C2—C3 | 119.16 (15) | C10—C11—H11 | 120.4 |
C1—C2—C6 | 120.06 (15) | O8—C12—C11 | 125.88 (15) |
C3—C2—C6 | 120.77 (14) | O8—C12—C13 | 113.64 (14) |
C4—C3—C2 | 118.66 (14) | C11—C12—C13 | 120.47 (15) |
C4—C3—C7 | 121.44 (15) | O7—C13—C14 | 118.00 (15) |
C2—C3—C7 | 119.87 (15) | O7—C13—C12 | 121.94 (15) |
O3—C4—C5 | 115.73 (15) | C14—C13—C12 | 120.06 (14) |
O3—C4—C3 | 123.78 (15) | O6—C14—C15 | 125.48 (15) |
C5—C4—C3 | 120.48 (15) | O6—C14—C13 | 114.76 (14) |
N1—C5—C4 | 118.00 (15) | C15—C14—C13 | 119.77 (15) |
N1—C5—C8 | 119.78 (14) | C14—C15—C10 | 119.72 (15) |
C4—C5—C8 | 122.21 (15) | C14—C15—H15 | 120.1 |
O1—C6—C2 | 110.61 (14) | C10—C15—H15 | 120.1 |
O1—C6—H6A | 109.5 | O8—C16—H16A | 109.5 |
C2—C6—H6A | 109.5 | O8—C16—H16B | 109.5 |
O1—C6—H6B | 109.5 | H16A—C16—H16B | 109.5 |
C2—C6—H6B | 109.5 | O8—C16—H16C | 109.5 |
H6A—C6—H6B | 108.1 | H16A—C16—H16C | 109.5 |
O2—C7—C3 | 113.71 (14) | H16B—C16—H16C | 109.5 |
O2—C7—H7A | 108.8 | O6—C17—H17A | 109.5 |
C3—C7—H7A | 108.8 | O6—C17—H17B | 109.5 |
O2—C7—H7B | 108.8 | H17A—C17—H17B | 109.5 |
C3—C7—H7B | 108.8 | O6—C17—H17C | 109.5 |
H7A—C7—H7B | 107.7 | H17A—C17—H17C | 109.5 |
C5—C8—H8A | 109.5 | H17B—C17—H17C | 109.5 |
C5—C8—H8B | 109.5 | | |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1N···O4 | 0.91 (2) | 1.77 (2) | 2.671 (2) | 171 (2) |
O3—H3O···O2 | 0.95 (4) | 1.83 (4) | 2.663 (2) | 144 (3) |
C8—H8A···O4 | 0.96 | 2.52 | 3.308 (2) | 139 |
C1—H1···O1i | 0.93 | 2.47 | 3.359 (2) | 158 |
O1—H1O···O5i | 0.85 (3) | 1.83 (3) | 2.663 (2) | 166 (3) |
C6—H6B···O5ii | 0.97 | 2.64 | 3.576 (3) | 161 |
O2—H2O···O4iii | 0.87 (4) | 1.77 (4) | 2.620 (2) | 165 (3) |
O7—H7O···O2iv | 0.89 (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) x−1, y−2, 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−·H2O | F(000) = 404 |
Mr = 381.37 | Dx = 1.418 Mg m−3 |
Monoclinic, P21 | Mo Kα radiation, λ = 0.71073 Å |
a = 7.2440 (3) Å | Cell parameters from 11173 reflections |
b = 17.1615 (5) Å | θ = 4–30° |
c = 7.2706 (2) Å | µ = 0.11 mm−1 |
β = 98.806 (2)° | T = 295 K |
V = 893.21 (5) Å3 | Prismatic, colourless |
Z = 2 | 0.35 × 0.22 × 0.13 mm |
Data collection top
Nonius Kappa CCD diffractometer | Rint = 0.034 |
φ scans and ω scans | θmax = 30.0°, θmin = 4.5° |
11173 measured reflections | h = −10→9 |
4578 independent reflections | k = −24→22 |
3822 reflections with I > 2σ(I) | l = −10→10 |
Refinement top
Refinement on F2 | Hydrogen site location: mixed |
Least-squares matrix: full | H 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 = 1.07 | Δρmax = 0.27 e Å−3 |
4578 reflections | Δρmin = −0.18 e Å−3 |
272 parameters | Absolute structure: Flack x determined using 1452 quotients [(I+)-(I-)]/[(I+)+(I-)]
(Parsons et al., 2013) |
1 restraint | Absolute 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 | x | y | z | Uiso*/Ueq | |
N1 | 0.8860 (3) | −0.19960 (10) | 1.1832 (2) | 0.0354 (4) | |
O1 | 0.7016 (3) | −0.39465 (12) | 0.8941 (2) | 0.0551 (5) | |
O2 | 0.9773 (4) | −0.40722 (13) | 1.6750 (3) | 0.0622 (6) | |
O3 | 1.0560 (3) | −0.26271 (12) | 1.6424 (2) | 0.0526 (4) | |
O4 | 0.7236 (2) | −0.12996 (9) | 0.7844 (2) | 0.0457 (4) | |
O5 | 0.8366 (3) | −0.05993 (9) | 1.0310 (2) | 0.0473 (4) | |
O6 | 0.4671 (3) | 0.36773 (9) | 0.5400 (2) | 0.0492 (4) | |
O7 | 0.6240 (3) | 0.35956 (10) | 0.8823 (2) | 0.0565 (5) | |
O1W | 0.5731 (3) | 0.00760 (11) | 1.2468 (2) | 0.0502 (4) | |
C1 | 0.8257 (3) | −0.26552 (12) | 1.0932 (3) | 0.0352 (4) | |
H1 | 0.7760 | −0.2635 | 0.9675 | 0.042* | |
C2 | 0.8367 (3) | −0.33573 (12) | 1.1852 (3) | 0.0325 (4) | |
C3 | 0.9116 (3) | −0.33702 (12) | 1.3759 (3) | 0.0331 (4) | |
C4 | 0.9767 (3) | −0.26757 (13) | 1.4613 (3) | 0.0356 (4) | |
C5 | 0.9623 (3) | −0.19785 (12) | 1.3625 (3) | 0.0352 (4) | |
C6 | 0.7702 (3) | −0.40987 (12) | 1.0846 (3) | 0.0384 (4) | |
H6A | 0.8727 | −0.4467 | 1.0934 | 0.046* | |
H6B | 0.6719 | −0.4330 | 1.1434 | 0.046* | |
C7 | 0.9194 (4) | −0.41369 (14) | 1.4799 (3) | 0.0466 (5) | |
H7A | 0.7965 | −0.4374 | 1.4580 | 0.056* | |
H7B | 1.0047 | −0.4483 | 1.4291 | 0.056* | |
C8 | 1.0285 (4) | −0.12139 (15) | 1.4478 (3) | 0.0464 (5) | |
H8A | 1.0056 | −0.0810 | 1.3557 | 0.070* | |
H8B | 1.1599 | −0.1243 | 1.4931 | 0.070* | |
H8C | 0.9622 | −0.1098 | 1.5492 | 0.070* | |
C9 | 0.7545 (3) | −0.06564 (11) | 0.8646 (3) | 0.0332 (4) | |
C10 | 0.6902 (3) | 0.00681 (12) | 0.7617 (3) | 0.0368 (4) | |
H10 | 0.6318 | 0.0027 | 0.6390 | 0.044* | |
C11 | 0.7130 (3) | 0.07718 (12) | 0.8386 (3) | 0.0332 (4) | |
H11 | 0.7754 | 0.0793 | 0.9602 | 0.040* | |
C12 | 0.6508 (3) | 0.15162 (11) | 0.7528 (3) | 0.0320 (4) | |
C13 | 0.6705 (3) | 0.21921 (12) | 0.8628 (3) | 0.0349 (4) | |
H13 | 0.7248 | 0.2159 | 0.9871 | 0.042* | |
C14 | 0.6101 (3) | 0.29043 (12) | 0.7888 (3) | 0.0365 (4) | |
C15 | 0.5249 (3) | 0.29579 (12) | 0.6022 (3) | 0.0363 (4) | |
C16 | 0.5067 (3) | 0.22952 (12) | 0.4926 (3) | 0.0370 (4) | |
H16 | 0.4518 | 0.2330 | 0.3686 | 0.044* | |
C17 | 0.5697 (3) | 0.15779 (12) | 0.5661 (3) | 0.0365 (4) | |
H17 | 0.5578 | 0.1137 | 0.4907 | 0.044* | |
C18 | 0.7096 (4) | 0.35938 (16) | 1.0716 (3) | 0.0537 (6) | |
H18A | 0.6440 | 0.3241 | 1.1411 | 0.081* | |
H18B | 0.7053 | 0.4109 | 1.1221 | 0.081* | |
H18C | 0.8373 | 0.3430 | 1.0797 | 0.081* | |
H1N | 0.879 (5) | −0.153 (3) | 1.116 (5) | 0.080 (11)* | |
H1O | 0.614 (4) | −0.428 (2) | 0.855 (4) | 0.046 (7)* | |
H2O | 0.877 (8) | −0.403 (3) | 1.737 (7) | 0.115 (18)* | |
H3O | 1.038 (6) | −0.313 (3) | 1.674 (6) | 0.081 (12)* | |
H6O | 0.396 (5) | 0.360 (3) | 0.422 (6) | 0.080 (11)* | |
H1W | 0.537 (6) | −0.035 (3) | 1.282 (6) | 0.078 (11)* | |
H2W | 0.674 (7) | −0.007 (3) | 1.196 (6) | 0.100 (14)* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
N1 | 0.0409 (9) | 0.0269 (8) | 0.0361 (8) | 0.0026 (7) | −0.0010 (7) | 0.0031 (7) |
O1 | 0.0745 (13) | 0.0494 (10) | 0.0396 (9) | −0.0207 (10) | 0.0032 (8) | −0.0049 (8) |
O2 | 0.0801 (14) | 0.0624 (13) | 0.0422 (9) | −0.0019 (11) | 0.0025 (9) | 0.0191 (9) |
O3 | 0.0712 (12) | 0.0515 (10) | 0.0313 (7) | 0.0014 (9) | −0.0048 (7) | −0.0008 (7) |
O4 | 0.0667 (10) | 0.0267 (7) | 0.0392 (8) | 0.0019 (7) | −0.0061 (7) | −0.0014 (6) |
O5 | 0.0688 (11) | 0.0296 (7) | 0.0376 (8) | 0.0047 (7) | −0.0103 (7) | 0.0000 (6) |
O6 | 0.0712 (11) | 0.0276 (8) | 0.0419 (8) | 0.0069 (8) | −0.0129 (7) | 0.0032 (6) |
O7 | 0.0924 (13) | 0.0285 (8) | 0.0404 (8) | 0.0096 (9) | −0.0163 (8) | −0.0027 (7) |
O1W | 0.0700 (12) | 0.0332 (8) | 0.0473 (9) | 0.0067 (8) | 0.0082 (8) | 0.0033 (7) |
C1 | 0.0406 (10) | 0.0300 (9) | 0.0333 (9) | 0.0005 (9) | −0.0001 (8) | 0.0016 (8) |
C2 | 0.0336 (10) | 0.0292 (9) | 0.0345 (9) | 0.0019 (8) | 0.0047 (7) | 0.0000 (8) |
C3 | 0.0360 (10) | 0.0309 (9) | 0.0330 (9) | 0.0039 (8) | 0.0079 (7) | 0.0029 (8) |
C4 | 0.0398 (10) | 0.0366 (10) | 0.0296 (9) | 0.0051 (9) | 0.0030 (7) | 0.0021 (8) |
C5 | 0.0368 (10) | 0.0331 (10) | 0.0348 (9) | 0.0010 (9) | 0.0021 (8) | −0.0023 (8) |
C6 | 0.0443 (11) | 0.0310 (10) | 0.0399 (10) | −0.0038 (9) | 0.0066 (8) | −0.0031 (8) |
C7 | 0.0655 (15) | 0.0356 (11) | 0.0404 (11) | 0.0078 (11) | 0.0135 (10) | 0.0098 (9) |
C8 | 0.0552 (13) | 0.0369 (11) | 0.0440 (11) | −0.0023 (10) | −0.0017 (9) | −0.0060 (9) |
C9 | 0.0392 (10) | 0.0262 (9) | 0.0333 (9) | 0.0041 (8) | 0.0025 (7) | 0.0028 (7) |
C10 | 0.0450 (11) | 0.0296 (9) | 0.0333 (9) | 0.0015 (9) | −0.0017 (8) | 0.0030 (8) |
C11 | 0.0349 (10) | 0.0289 (9) | 0.0347 (9) | 0.0010 (8) | 0.0020 (7) | 0.0036 (8) |
C12 | 0.0331 (10) | 0.0255 (9) | 0.0365 (9) | 0.0000 (8) | 0.0022 (7) | 0.0032 (8) |
C13 | 0.0405 (10) | 0.0296 (10) | 0.0323 (9) | 0.0009 (8) | −0.0017 (7) | 0.0020 (8) |
C14 | 0.0426 (11) | 0.0280 (10) | 0.0366 (10) | −0.0003 (9) | −0.0014 (8) | −0.0014 (8) |
C15 | 0.0414 (11) | 0.0293 (9) | 0.0360 (10) | 0.0020 (9) | −0.0005 (8) | 0.0059 (8) |
C16 | 0.0438 (11) | 0.0312 (9) | 0.0333 (9) | −0.0003 (9) | −0.0030 (8) | 0.0031 (8) |
C17 | 0.0431 (11) | 0.0293 (9) | 0.0354 (9) | 0.0000 (9) | 0.0009 (8) | 0.0006 (8) |
C18 | 0.0772 (17) | 0.0407 (12) | 0.0377 (11) | 0.0052 (12) | −0.0088 (11) | −0.0075 (10) |
Geometric parameters (Å, º) top
N1—C5 | 1.336 (3) | C6—H6A | 0.9700 |
N1—C1 | 1.346 (3) | C6—H6B | 0.9700 |
N1—H1N | 0.93 (5) | C7—H7A | 0.9700 |
O1—C6 | 1.423 (3) | C7—H7B | 0.9700 |
O1—H1O | 0.87 (3) | C8—H8A | 0.9600 |
O2—C7 | 1.421 (3) | C8—H8B | 0.9600 |
O2—H2O | 0.92 (5) | C8—H8C | 0.9600 |
O3—C4 | 1.356 (2) | C9—C10 | 1.488 (3) |
O3—H3O | 0.91 (5) | C10—C11 | 1.330 (3) |
O4—C9 | 1.253 (3) | C10—H10 | 0.9300 |
O5—C9 | 1.267 (3) | C11—C12 | 1.462 (3) |
O6—C15 | 1.359 (3) | C11—H11 | 0.9300 |
O6—H6O | 0.94 (4) | C12—C17 | 1.398 (3) |
O7—C14 | 1.363 (3) | C12—C13 | 1.404 (3) |
O7—C18 | 1.421 (3) | C13—C14 | 1.379 (3) |
O1W—H1W | 0.82 (5) | C13—H13 | 0.9300 |
O1W—H2W | 0.90 (5) | C14—C15 | 1.405 (3) |
C1—C2 | 1.374 (3) | C15—C16 | 1.383 (3) |
C1—H1 | 0.9300 | C16—C17 | 1.391 (3) |
C2—C3 | 1.409 (3) | C16—H16 | 0.9300 |
C2—C6 | 1.509 (3) | C17—H17 | 0.9300 |
C3—C4 | 1.393 (3) | C18—H18A | 0.9600 |
C3—C7 | 1.514 (3) | C18—H18B | 0.9600 |
C4—C5 | 1.391 (3) | C18—H18C | 0.9600 |
C5—C8 | 1.498 (3) | | |
| | | |
C5—N1—C1 | 123.26 (18) | H8A—C8—H8B | 109.5 |
C5—N1—H1N | 118 (2) | C5—C8—H8C | 109.5 |
C1—N1—H1N | 118 (2) | H8A—C8—H8C | 109.5 |
C6—O1—H1O | 109.4 (19) | H8B—C8—H8C | 109.5 |
C7—O2—H2O | 111 (3) | O4—C9—O5 | 122.47 (18) |
C4—O3—H3O | 98 (3) | O4—C9—C10 | 118.83 (17) |
C15—O6—H6O | 106 (3) | O5—C9—C10 | 118.69 (17) |
C14—O7—C18 | 117.98 (18) | C11—C10—C9 | 122.54 (17) |
H1W—O1W—H2W | 102 (4) | C11—C10—H10 | 118.7 |
N1—C1—C2 | 120.66 (18) | C9—C10—H10 | 118.7 |
N1—C1—H1 | 119.7 | C10—C11—C12 | 127.11 (18) |
C2—C1—H1 | 119.7 | C10—C11—H11 | 116.4 |
C1—C2—C3 | 118.51 (19) | C12—C11—H11 | 116.4 |
C1—C2—C6 | 120.87 (18) | C17—C12—C13 | 118.80 (18) |
C3—C2—C6 | 120.62 (18) | C17—C12—C11 | 122.46 (18) |
C4—C3—C2 | 118.58 (18) | C13—C12—C11 | 118.73 (17) |
C4—C3—C7 | 122.45 (18) | C14—C13—C12 | 120.74 (18) |
C2—C3—C7 | 118.97 (19) | C14—C13—H13 | 119.6 |
O3—C4—C5 | 115.8 (2) | C12—C13—H13 | 119.6 |
O3—C4—C3 | 123.4 (2) | O7—C14—C13 | 125.58 (18) |
C5—C4—C3 | 120.81 (17) | O7—C14—C15 | 114.36 (18) |
N1—C5—C4 | 118.13 (18) | C13—C14—C15 | 120.06 (18) |
N1—C5—C8 | 118.81 (19) | O6—C15—C16 | 123.92 (18) |
C4—C5—C8 | 123.06 (18) | O6—C15—C14 | 116.62 (19) |
O1—C6—C2 | 110.78 (17) | C16—C15—C14 | 119.45 (18) |
O1—C6—H6A | 109.5 | C15—C16—C17 | 120.63 (19) |
C2—C6—H6A | 109.5 | C15—C16—H16 | 119.7 |
O1—C6—H6B | 109.5 | C17—C16—H16 | 119.7 |
C2—C6—H6B | 109.5 | C16—C17—C12 | 120.29 (19) |
H6A—C6—H6B | 108.1 | C16—C17—H17 | 119.9 |
O2—C7—C3 | 114.4 (2) | C12—C17—H17 | 119.9 |
O2—C7—H7A | 108.7 | O7—C18—H18A | 109.5 |
C3—C7—H7A | 108.7 | O7—C18—H18B | 109.5 |
O2—C7—H7B | 108.7 | H18A—C18—H18B | 109.5 |
C3—C7—H7B | 108.7 | O7—C18—H18C | 109.5 |
H7A—C7—H7B | 107.6 | H18A—C18—H18C | 109.5 |
C5—C8—H8A | 109.5 | H18B—C18—H18C | 109.5 |
C5—C8—H8B | 109.5 | | |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1N···O5 | 0.93 (4) | 1.73 (5) | 2.641 (2) | 166 (4) |
O3—H3O···O2 | 0.90 (5) | 1.68 (5) | 2.564 (3) | 165 (4) |
O1W—H2W···O5 | 0.90 (5) | 2.02 (5) | 2.893 (3) | 161 (5) |
C8—H8A···O5 | 0.96 | 2.51 | 3.307 (3) | 140 |
O2—H2O···O1i | 0.91 (6) | 1.84 (6) | 2.747 (3) | 171 (5) |
C8—H8C···O4i | 0.96 | 2.63 | 3.541 (3) | 158 |
C17—H17···O1Wii | 0.93 | 2.55 | 3.472 (3) | 167 |
O6—H6O···O4iii | 0.94 (4) | 1.62 (4) | 2.545 (2) | 166 (4) |
O1—H1O···O1Wiv | 0.86 (3) | 1.82 (3) | 2.683 (3) | 175 (3) |
O1W—H1W···O6iviv | 0.82 (5) | 2.12 (5) | 2.896 (2) | 156 (4) |
O1W—H1W···O7iviv | 0.82 (5) | 2.37 (5) | 2.994 (3) | 132 (4) |
Symmetry codes: (i) x, y, z+1; (ii) x, y, z−1; (iii) −x+1, y+1/2, −z+1; (iv) −x+1, y−1/2, −z+2. |
Structural parameters for hydrogen bonds and π–π interactions
(Å, °) for (1) and (2) topCg represents a ring centroid. |
D—H···A | D—H | D···A | H···A | D—H···A |
Cocrystal (1) | | | | |
N1—H1N···O4 | 0.91 (2) | 2.671 (2) | 1.77 (2) | 171 (2) |
O3—H3O···O2 | 0.95 (4) | 2.663 (2) | 1.83 (4) | 144 (3) |
C8—H8A···O4 | 0.96 | 3.308 (2) | 2.52 | 139 |
C1—H1···O1i | 0.93 | 3.359 (2) | 2.47 | 158 |
O1—H1O···O5i | 0.85 (3) | 2.663 (2) | 1.83 (3) | 166 (3) |
C6—H6B···O5ii | 0.97 | 3.576 (3) | 2.64 | 161 |
O2—H2O···O4iii | 0.87 (4) | 2.620 (2) | 1.77 (4) | 165 (3) |
O7—H7O···O2iv | 0.89 (2) | 2.728 (1) | 1.93 (2) | 146 (3) |
| | | | |
π–π interactions | | | | |
Cg(C10–C15···Cg(N1/C1–C5)v | 3.552 | | | |
Cg(C10–C15)···Cg(N1/C1–C5)vi | 3.577 | | | |
| | | | |
Cocrystal (2) | | | | |
N1—H1N···O5 | 0.93 (4) | 2.641 (2) | 1.73 (5) | 166 (4) |
O3—H3O···O2 | 0.90 (5) | 2.564 (3) | 1.68 (5) | 165 (4) |
O1W–H2W···O5 | 0.90 (5) | 2.893 (3) | 2.02 (5) | 161 (5) |
C8—H8A···O5 | 0.96 | 3.307 (3) | 2.51 | 140 |
O2—H2O···O1vii | 0.91 (6) | 2.747 (3) | 1.84 (6) | 171 (5) |
C8—H8C···O4vii | 0.96 | 3.541 (3) | 2.63 | 158 |
C17—H17···O1Wviii | 0.93 | 3.472 (3) | 2.55 | 167 |
O6—H6O···O4ix | 0.94 (4) | 2.545 (2) | 1.62 (4) | 166 (4) |
O1—H1O···O1Wx | 0.86 (3) | 2.683 (3) | 1.82 (3) | 175 (3) |
O1W—H1W···O6x | 0.82 (5) | 2.896 (2) | 2.12 (5) | 156 (4) |
O1W—H1W···O7x | 0.82 (5) | 2.994 (3) | 2.37 (5) | 132 (4) |
| | | | |
π–π interactions | | | | |
Cg(C12–C17)···Cg(N1/C1–C5)xi | 3.608 | | | |
Cg(C12–C17)···Cg(N1/C1–C5)xii | 3.671 | | | |
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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