New pharmaceutical salts containing pyridoxine

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 pK_a 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.

Computing details

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)

Crystal data

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) Å^3	0.52 × 0.20 × 0.09 mm

Data collection

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

Refinement on F^2	Hydrogen site location: mixed
Least-squares matrix: full	H atoms treated by a mixture of independent and constrained refinement
R[F^2 > 2σ(F^2)] = 0.053	w = 1/[σ^2(Fo^2) + (0.0972P)^2 + 0.1657P] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 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+0.001xFc^2λ^3/sin(2θ)]^-1/4
0 restraints	Extinction coefficient: 0.049 (12)

Special details

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 (Ų)

	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 (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
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)

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)

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···O1^i	0.93	2.47	3.359 (2)	158
O1—H1O···O5^i	0.85 (3)	1.83 (3)	2.663 (2)	166 (3)
C6—H6B···O5^ii	0.97	2.64	3.576 (3)	161
O2—H2O···O4^iii	0.87 (4)	1.77 (4)	2.620 (2)	165 (3)
O7—H7O···O2^iv	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)

Crystal data

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) Å^3	Prismatic, colourless
Z = 2	0.35 × 0.22 × 0.13 mm

Data collection

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

Refinement on F^2	Hydrogen site location: mixed
Least-squares matrix: full	H atoms treated by a mixture of independent and constrained refinement
R[F^2 > 2σ(F^2)] = 0.040	w = 1/[σ^2(Fo^2) + (0.063P)^2 + 0.0278P] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 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

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 (Ų)

	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 (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
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)

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)

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···O1^i	0.91 (6)	1.84 (6)	2.747 (3)	171 (5)
C8—H8C···O4^i	0.96	2.63	3.541 (3)	158
C17—H17···O1W^ii	0.93	2.55	3.472 (3)	167
O6—H6O···O4^iii	0.94 (4)	1.62 (4)	2.545 (2)	166 (4)
O1—H1O···O1W^iv	0.86 (3)	1.82 (3)	2.683 (3)	175 (3)
O1W—H1W···O6iv^iv	0.82 (5)	2.12 (5)	2.896 (2)	156 (4)
O1W—H1W···O7iv^iv	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.