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In the crystal structure of the title compound, C6H8N3O+·C7H5O6S·H2O, cations, anions and water mol­ecules are linked by a number of C/N/O—H...O and N—H...N hydrogen bonds into a three-dimensional network.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807023124/lh2389sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536807023124/lh2389Isup2.hkl
Contains datablock I

CCDC reference: 651475

Key indicators

  • Single-crystal X-ray study
  • T = 299 K
  • Mean [sigma](C-C) = 0.003 Å
  • R factor = 0.057
  • wR factor = 0.130
  • Data-to-parameter ratio = 15.0

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ? PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor .... 2.03
Alert level G PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints ....... 9
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 2 ALERT level C = Check and explain 1 ALERT level G = General alerts; check 1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 1 ALERT type 2 Indicator that the structure model may be wrong or deficient 1 ALERT type 3 Indicator that the structure quality may be low 0 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check

Comment top

As part of our continuing studies on the inter-ion and intra-associative H-bonding interactions of organic superstructures (Xie, 2007a, b)), we report herein the crystal structure of (I) formed by isonicid and sulfosalicylic acid.

In (I) (Fig.1), like the earlier reported structure (Xie, 2007a), the acid H atom is released from the sulfonic group to pyridine N atom forming the stechiometrical 1:1 organic salt with one water solvent molecule incorporated into the selected asymmetric unit.

In the supramolecular structure, the molecules are linked by a combination of C (or N, O)–H···O and N–H···N hydrogen bonds into a three-dimensional network whose formation is readily analysed in terms of three substructures. In the first of these substructures, by a combination of the first five hydrognen bonds listed in table 1 the 4-(Hydrazinecarbonyl)pyridinium cations and water molecules are linked into a two-dimensional network running parallel to the (101) direction (Fig.2). The second substructure is formed by linking of the sulphonate anions via three O–H···O hydrogen bonds, i.e. O3–H3B···O7iii, O4–H4A···O2 and O4–H4A···O5iv, [symmetry codes as in Table 1] so forming another two-dimensional framework running parallel to the (101) direction (Fig.3). The third substructure is the combination of the last four hydrogen bonds in Tabel 1 which link the adjacent (101) planes into a three-dimensional network (Fig.4).

There are two aromatic ππ stacking interactions in the structure of (I), which serve to reinforce the adjacent (101) sheets. The phenyl ring in the molecule at (x,y,z) and the pyridine ring in the molecule at (1/2 - x,1 - y,-1/2 + z), which lie in the different (101) sheets, are almost parallel, with a dihedral angle between the two rings of only 3.53 (1)°, an interplanar spacing of 3.243 (1) Å, and ring-centroid separation of 3.615 (1) Å PLATON (Spek,2003).

Related literature top

The author has recently determined the crystal structures of two closely related compounds (Xie 2007a,b).

Experimental top

All reagents and solvents were used as obtained without further purification. Equivalent molar amounts of isonicid and sulfosalicylic acid were dissolved in 95% methanol (10 ml). The mixture was stirred for ten minutes at ambient temperature and then filtered. The resulting colourless solution was kept in air for two days. colourless crystals of (I) suitable for single-crystal X-ray diffraction analysis were grown by slow evaporation of the solution at the bottom of the vessel.

Refinement top

H atoms bonded to C atoms were placed in calculated positions with C—H = 0.93 Å and Uiso(H) = 1.2Ueq(C). All the other H atoms were located from the difference maps with the constraints of N—H = 0.86 (1) Å, Uiso(H) = 1.2Ueq(N); O—H = 0.82 (1) Å, H—H = 1.39 (1) Å and Uiso(H) = 1.5Ueq(O).

Structure description top

As part of our continuing studies on the inter-ion and intra-associative H-bonding interactions of organic superstructures (Xie, 2007a, b)), we report herein the crystal structure of (I) formed by isonicid and sulfosalicylic acid.

In (I) (Fig.1), like the earlier reported structure (Xie, 2007a), the acid H atom is released from the sulfonic group to pyridine N atom forming the stechiometrical 1:1 organic salt with one water solvent molecule incorporated into the selected asymmetric unit.

In the supramolecular structure, the molecules are linked by a combination of C (or N, O)–H···O and N–H···N hydrogen bonds into a three-dimensional network whose formation is readily analysed in terms of three substructures. In the first of these substructures, by a combination of the first five hydrognen bonds listed in table 1 the 4-(Hydrazinecarbonyl)pyridinium cations and water molecules are linked into a two-dimensional network running parallel to the (101) direction (Fig.2). The second substructure is formed by linking of the sulphonate anions via three O–H···O hydrogen bonds, i.e. O3–H3B···O7iii, O4–H4A···O2 and O4–H4A···O5iv, [symmetry codes as in Table 1] so forming another two-dimensional framework running parallel to the (101) direction (Fig.3). The third substructure is the combination of the last four hydrogen bonds in Tabel 1 which link the adjacent (101) planes into a three-dimensional network (Fig.4).

There are two aromatic ππ stacking interactions in the structure of (I), which serve to reinforce the adjacent (101) sheets. The phenyl ring in the molecule at (x,y,z) and the pyridine ring in the molecule at (1/2 - x,1 - y,-1/2 + z), which lie in the different (101) sheets, are almost parallel, with a dihedral angle between the two rings of only 3.53 (1)°, an interplanar spacing of 3.243 (1) Å, and ring-centroid separation of 3.615 (1) Å PLATON (Spek,2003).

The author has recently determined the crystal structures of two closely related compounds (Xie 2007a,b).

Computing details top

Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: PLATON.

Figures top
[Figure 1] Fig. 1. Molecular structure of (I), showing the atom-numbering scheme. Displacement ellipsoids are drawn at the 50% probability level. Inter-ion and intermolecular hydrogen bonding are shown as dashed lines.
[Figure 2] Fig. 2. Part of the crystal structure of (I), showing the formation of the (101) sheet generated by the hydrogen bonds between the cations and water solvent molecules. Hydrogen bonds are shown as dashed lines. For the sake of clarity, H atoms and intermolecular hydrogen bonding not involved in the motif have been omitted. Atoms marked with a hash(#) or a dollar sign($) are at the symmetry positions (1/2 + x, y, 3/2 - z) and (1/2 - x, 1 - y, 1/2 + z), respectively.
[Figure 3] Fig. 3. Part of the crystal structure of (I), showing the formation of the (101) sheet generated by the hydrogen bonds between the anions. Hydrogen bonds are shown as dashed lines. For the sake of clarity, H atoms and intermolecular hydrogen bonds not involved in the motif have been omitted. Atoms marked with a hash(#) or a dollar sign($) are at the symmetry positions (1/2 + x, y, 1/2 - z) and (x, 3/2 - y, -1/2 + z), respectively.
[Figure 4] Fig. 4. Part of the crystal structure of (I), showing the formation of the three-dimensional network generated by the hydrogen bonds. Hydrogen bonds are shown as dashed lines. For the sake of clarity, H atoms and intermolecular hydrogen bonds not involved in the motif have been omitted.
4-(Hydrazinecarbonyl)pyridinium 3-carboxy-4-hydroxybenzenesulfonate monohydrate top
Crystal data top
C6H8N3O+·C7H5O6S·H2OF(000) = 1552
Mr = 373.34Dx = 1.625 Mg m3
Orthorhombic, PbcaMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2abCell parameters from 2943 reflections
a = 13.7628 (8) Åθ = 2.8–21.4°
b = 13.0656 (8) ŵ = 0.27 mm1
c = 16.9752 (10) ÅT = 299 K
V = 3052.5 (3) Å3Plate, colourless
Z = 80.30 × 0.20 × 0.04 mm
Data collection top
Bruker SMART APEX CCD area-detector
diffractometer
3747 independent reflections
Radiation source: fine focus sealed Siemens Mo tube2727 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.075
0.3° wide ω exposures scansθmax = 28.3°, θmin = 2.4°
Absorption correction: multi-scan
(SADABS; Sheldrick, 2001)
h = 1818
Tmin = 0.927, Tmax = 0.990k = 1717
33729 measured reflectionsl = 2221
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)] = 0.057Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.130H atoms treated by a mixture of independent and constrained refinement
S = 1.06 w = 1/[σ2(Fo2) + (0.0503P)2 + 1.8424P]
where P = (Fo2 + 2Fc2)/3
3747 reflections(Δ/σ)max < 0.001
250 parametersΔρmax = 0.31 e Å3
9 restraintsΔρmin = 0.34 e Å3
Crystal data top
C6H8N3O+·C7H5O6S·H2OV = 3052.5 (3) Å3
Mr = 373.34Z = 8
Orthorhombic, PbcaMo Kα radiation
a = 13.7628 (8) ŵ = 0.27 mm1
b = 13.0656 (8) ÅT = 299 K
c = 16.9752 (10) Å0.30 × 0.20 × 0.04 mm
Data collection top
Bruker SMART APEX CCD area-detector
diffractometer
3747 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 2001)
2727 reflections with I > 2σ(I)
Tmin = 0.927, Tmax = 0.990Rint = 0.075
33729 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0579 restraints
wR(F2) = 0.130H atoms treated by a mixture of independent and constrained refinement
S = 1.06Δρmax = 0.31 e Å3
3747 reflectionsΔρmin = 0.34 e Å3
250 parameters
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.

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
C10.17378 (17)0.51847 (17)0.82574 (12)0.0254 (5)
C20.27410 (17)0.52771 (19)0.83228 (13)0.0312 (5)
H20.31210.53680.78750.037*
C30.31671 (19)0.52328 (19)0.90534 (14)0.0354 (6)
H30.38380.52850.91010.042*
C40.16537 (19)0.5029 (2)0.96546 (14)0.0392 (6)
H40.12920.49491.01130.047*
C50.11965 (18)0.5060 (2)0.89398 (14)0.0339 (6)
H50.05240.49970.89110.041*
C60.11982 (17)0.51932 (17)0.74783 (13)0.0266 (5)
C70.15251 (16)0.71604 (18)0.26384 (13)0.0267 (5)
C80.24789 (16)0.72193 (17)0.29228 (13)0.0271 (5)
C90.26353 (16)0.73103 (18)0.37378 (14)0.0287 (5)
H90.32670.73490.39310.034*
C100.18697 (17)0.73430 (17)0.42491 (13)0.0279 (5)
H100.19810.74060.47870.033*
C110.09111 (16)0.72820 (17)0.39610 (12)0.0243 (5)
C120.07484 (16)0.71956 (18)0.31632 (13)0.0269 (5)
H120.01150.71610.29740.032*
C130.13520 (18)0.7073 (2)0.17783 (13)0.0329 (6)
N10.13200 (16)0.51270 (19)0.60756 (12)0.0363 (5)
H1A0.0923 (16)0.5630 (15)0.6003 (17)0.044*
H1B0.0998 (18)0.4563 (13)0.6098 (17)0.044*
N20.17413 (14)0.52155 (17)0.68322 (11)0.0312 (5)
H2A0.2359 (8)0.528 (2)0.6823 (15)0.037*
N30.26167 (17)0.51140 (17)0.96953 (11)0.0358 (5)
H3A0.2938 (18)0.509 (2)1.0131 (10)0.043*
O10.03087 (13)0.51570 (15)0.74565 (10)0.0406 (5)
O20.20020 (14)0.70257 (19)0.12983 (10)0.0564 (6)
O30.04337 (14)0.7035 (2)0.15867 (10)0.0533 (6)
H3B0.036 (3)0.695 (3)0.1110 (7)0.080*
O40.32670 (13)0.71925 (15)0.24516 (10)0.0408 (5)
H4A0.306 (2)0.715 (3)0.2000 (9)0.061*
O50.09471 (12)0.73591 (16)0.41419 (10)0.0439 (5)
O60.00170 (13)0.63684 (15)0.50742 (11)0.0458 (5)
O70.00528 (12)0.82175 (14)0.51056 (9)0.0366 (4)
O80.37530 (13)0.56058 (16)0.65203 (11)0.0428 (5)
H8A0.381 (2)0.6196 (12)0.6353 (18)0.064*
H8B0.4214 (16)0.543 (2)0.6807 (16)0.064*
S10.00779 (4)0.73054 (5)0.46210 (3)0.02779 (17)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0319 (12)0.0238 (11)0.0204 (11)0.0015 (9)0.0018 (9)0.0019 (9)
C20.0328 (13)0.0360 (14)0.0246 (11)0.0057 (11)0.0009 (10)0.0011 (10)
C30.0353 (14)0.0395 (15)0.0313 (13)0.0032 (11)0.0056 (11)0.0002 (11)
C40.0418 (16)0.0542 (17)0.0216 (12)0.0109 (13)0.0049 (11)0.0042 (11)
C50.0298 (13)0.0473 (16)0.0247 (12)0.0072 (11)0.0025 (10)0.0034 (11)
C60.0281 (13)0.0297 (12)0.0219 (11)0.0009 (9)0.0009 (9)0.0006 (9)
C70.0267 (12)0.0320 (13)0.0215 (11)0.0002 (9)0.0001 (9)0.0032 (9)
C80.0258 (11)0.0261 (12)0.0293 (12)0.0010 (9)0.0013 (10)0.0031 (10)
C90.0232 (11)0.0293 (12)0.0336 (12)0.0002 (10)0.0057 (9)0.0003 (10)
C100.0332 (12)0.0288 (12)0.0216 (11)0.0012 (10)0.0043 (9)0.0005 (9)
C110.0271 (11)0.0258 (12)0.0200 (10)0.0007 (9)0.0000 (9)0.0032 (9)
C120.0252 (11)0.0332 (13)0.0225 (11)0.0005 (9)0.0030 (9)0.0033 (10)
C130.0316 (13)0.0459 (15)0.0211 (11)0.0023 (11)0.0004 (10)0.0036 (10)
N10.0335 (12)0.0554 (15)0.0201 (10)0.0043 (10)0.0038 (9)0.0007 (10)
N20.0255 (10)0.0505 (13)0.0177 (9)0.0053 (9)0.0023 (8)0.0015 (9)
N30.0487 (14)0.0391 (12)0.0197 (10)0.0066 (10)0.0087 (9)0.0008 (9)
O10.0267 (9)0.0676 (13)0.0275 (9)0.0010 (8)0.0006 (7)0.0022 (9)
O20.0362 (11)0.1076 (18)0.0252 (9)0.0048 (11)0.0060 (8)0.0027 (11)
O30.0332 (10)0.1089 (18)0.0178 (9)0.0039 (11)0.0022 (8)0.0001 (10)
O40.0276 (9)0.0624 (13)0.0323 (9)0.0007 (8)0.0049 (8)0.0030 (9)
O50.0254 (9)0.0791 (14)0.0274 (9)0.0032 (9)0.0039 (7)0.0009 (9)
O60.0473 (11)0.0475 (12)0.0425 (11)0.0055 (9)0.0058 (9)0.0184 (9)
O70.0392 (10)0.0483 (11)0.0224 (8)0.0025 (8)0.0005 (7)0.0048 (8)
O80.0297 (10)0.0618 (14)0.0369 (11)0.0034 (9)0.0004 (8)0.0022 (9)
S10.0253 (3)0.0402 (4)0.0178 (3)0.0019 (2)0.0011 (2)0.0033 (2)
Geometric parameters (Å, º) top
C1—C51.387 (3)C10—C111.409 (3)
C1—C21.390 (3)C10—H100.9300
C1—C61.517 (3)C11—C121.377 (3)
C2—C31.373 (3)C11—S11.763 (2)
C2—H20.9300C12—H120.9300
C3—N31.336 (3)C13—O21.212 (3)
C3—H30.9300C13—O31.306 (3)
C4—N31.332 (3)N1—N21.414 (3)
C4—C51.367 (3)N1—H1A0.864 (10)
C4—H40.9300N1—H1B0.861 (10)
C5—H50.9300N2—H2A0.855 (10)
C6—O11.226 (3)N3—H3A0.862 (10)
C6—N21.328 (3)O3—H3B0.823 (10)
C7—C121.392 (3)O4—H4A0.821 (10)
C7—C81.401 (3)O5—S11.4482 (17)
C7—C131.484 (3)O6—S11.4484 (18)
C8—O41.348 (3)O7—S11.4593 (18)
C8—C91.405 (3)O8—H8A0.826 (10)
C9—C101.366 (3)O8—H8B0.832 (10)
C9—H90.9300
C5—C1—C2118.5 (2)C12—C11—C10119.9 (2)
C5—C1—C6117.8 (2)C12—C11—S1120.04 (17)
C2—C1—C6123.7 (2)C10—C11—S1120.09 (17)
C3—C2—C1119.5 (2)C11—C12—C7120.5 (2)
C3—C2—H2120.2C11—C12—H12119.8
C1—C2—H2120.2C7—C12—H12119.8
N3—C3—C2120.0 (2)O2—C13—O3123.0 (2)
N3—C3—H3120.0O2—C13—C7123.2 (2)
C2—C3—H3120.0O3—C13—C7113.8 (2)
N3—C4—C5120.1 (2)N2—N1—H1A109.1 (19)
N3—C4—H4119.9N2—N1—H1B103.9 (19)
C5—C4—H4119.9H1A—N1—H1B109 (3)
C4—C5—C1119.8 (2)C6—N2—N1121.2 (2)
C4—C5—H5120.1C6—N2—H2A125.3 (18)
C1—C5—H5120.1N1—N2—H2A113.5 (18)
O1—C6—N2122.6 (2)C4—N3—C3122.1 (2)
O1—C6—C1121.0 (2)C4—N3—H3A123.5 (19)
N2—C6—C1116.4 (2)C3—N3—H3A114.4 (19)
C12—C7—C8119.8 (2)C13—O3—H3B112 (3)
C12—C7—C13120.6 (2)C8—O4—H4A106 (2)
C8—C7—C13119.6 (2)S1—O6—H1A140.0 (7)
O4—C8—C7123.2 (2)H2A—O8—H8A112 (2)
O4—C8—C9117.6 (2)H2A—O8—H8B121 (2)
C7—C8—C9119.2 (2)H8A—O8—H8B112.5 (17)
C10—C9—C8120.7 (2)O5—S1—O6112.77 (12)
C10—C9—H9119.7O5—S1—O7112.27 (11)
C8—C9—H9119.7O6—S1—O7112.56 (11)
C9—C10—C11120.0 (2)O5—S1—C11106.37 (10)
C9—C10—H10120.0O6—S1—C11106.15 (11)
C11—C10—H10120.0O7—S1—C11106.09 (10)
C5—C1—C2—C30.6 (4)S1—C11—C12—C7178.99 (18)
C6—C1—C2—C3178.2 (2)C8—C7—C12—C110.4 (3)
C1—C2—C3—N30.8 (4)C13—C7—C12—C11179.6 (2)
N3—C4—C5—C10.3 (4)C12—C7—C13—O2179.0 (3)
C2—C1—C5—C40.0 (4)C8—C7—C13—O21.8 (4)
C6—C1—C5—C4178.8 (2)C12—C7—C13—O30.1 (3)
C5—C1—C6—O14.6 (3)C8—C7—C13—O3179.3 (2)
C2—C1—C6—O1176.6 (2)O1—C6—N2—N14.4 (4)
C5—C1—C6—N2173.8 (2)C1—C6—N2—N1173.9 (2)
C2—C1—C6—N25.1 (3)C5—C4—N3—C30.1 (4)
C12—C7—C8—O4179.9 (2)C2—C3—N3—C40.4 (4)
C13—C7—C8—O40.6 (4)H1A—O6—S1—O5174.7 (10)
C12—C7—C8—C90.2 (3)H1A—O6—S1—O746.4 (10)
C13—C7—C8—C9179.5 (2)H1A—O6—S1—C1169.2 (10)
O4—C8—C9—C10179.9 (2)C12—C11—S1—O57.5 (2)
C7—C8—C9—C100.1 (3)C10—C11—S1—O5173.08 (19)
C8—C9—C10—C110.2 (3)C12—C11—S1—O6112.9 (2)
C9—C10—C11—C120.4 (3)C10—C11—S1—O666.6 (2)
C9—C10—C11—S1179.08 (18)C12—C11—S1—O7127.18 (19)
C10—C11—C12—C70.5 (3)C10—C11—S1—O753.4 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C2—H2···O80.932.483.389 (3)166
C4—H4···O8i0.932.503.321 (3)148
N2—H2A···O80.86 (1)2.03 (1)2.865 (3)165 (2)
N3—H3A···N1i0.86 (1)1.92 (1)2.780 (3)173 (3)
O8—H8B···O1ii0.83 (1)1.99 (1)2.819 (3)174 (3)
O3—H3B···O7iii0.82 (1)1.77 (1)2.589 (2)174 (4)
O4—H4A···O20.82 (1)1.89 (2)2.629 (3)150 (3)
O4—H4A···O5iv0.82 (1)2.39 (3)2.921 (2)123 (3)
C3—H3···O6ii0.932.543.262 (3)135
N1—H1A···O60.86 (1)2.26 (2)2.984 (3)142 (2)
N1—H1B···O5v0.86 (1)2.55 (2)3.309 (3)148 (2)
O8—H8A···O5vi0.83 (1)2.09 (1)2.916 (3)175 (3)
Symmetry codes: (i) x+1/2, y+1, z+1/2; (ii) x+1/2, y, z+3/2; (iii) x, y+3/2, z1/2; (iv) x+1/2, y, z+1/2; (v) x, y+1, z+1; (vi) x+1/2, y+3/2, z+1.

Experimental details

Crystal data
Chemical formulaC6H8N3O+·C7H5O6S·H2O
Mr373.34
Crystal system, space groupOrthorhombic, Pbca
Temperature (K)299
a, b, c (Å)13.7628 (8), 13.0656 (8), 16.9752 (10)
V3)3052.5 (3)
Z8
Radiation typeMo Kα
µ (mm1)0.27
Crystal size (mm)0.30 × 0.20 × 0.04
Data collection
DiffractometerBruker SMART APEX CCD area-detector
Absorption correctionMulti-scan
(SADABS; Sheldrick, 2001)
Tmin, Tmax0.927, 0.990
No. of measured, independent and
observed [I > 2σ(I)] reflections
33729, 3747, 2727
Rint0.075
(sin θ/λ)max1)0.667
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.057, 0.130, 1.06
No. of reflections3747
No. of parameters250
No. of restraints9
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)0.31, 0.34

Computer programs: SMART (Bruker, 2001), SAINT (Bruker, 2001), SAINT, SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), PLATON (Spek, 2003), PLATON.

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C2—H2···O80.932.483.389 (3)166.3
C4—H4···O8i0.932.503.321 (3)147.8
N2—H2A···O80.855 (10)2.030 (12)2.865 (3)165 (2)
N3—H3A···N1i0.862 (10)1.923 (11)2.780 (3)173 (3)
O8—H8B···O1ii0.832 (10)1.990 (11)2.819 (3)174 (3)
O3—H3B···O7iii0.823 (10)1.769 (11)2.589 (2)174 (4)
O4—H4A···O20.821 (10)1.886 (18)2.629 (3)150 (3)
O4—H4A···O5iv0.821 (10)2.39 (3)2.921 (2)123 (3)
C3—H3···O6ii0.932.543.262 (3)134.9
N1—H1A···O60.864 (10)2.256 (19)2.984 (3)142 (2)
N1—H1B···O5v0.861 (10)2.545 (17)3.309 (3)148 (2)
O8—H8A···O5vi0.826 (10)2.093 (11)2.916 (3)175 (3)
Symmetry codes: (i) x+1/2, y+1, z+1/2; (ii) x+1/2, y, z+3/2; (iii) x, y+3/2, z1/2; (iv) x+1/2, y, z+1/2; (v) x, y+1, z+1; (vi) x+1/2, y+3/2, z+1.
 

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