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The crystal structure of the title compound, C7H10N+·C4H5O6·1.5H2O, is based on a three-dimensional supramol­ecular framework constructed through N—H...O hydrogen bonds and weak π–π inter­actions.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806008579/bh2004sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806008579/bh2004Isup2.hkl
Contains datablock I

CCDC reference: 604966

Key indicators

  • Single-crystal X-ray study
  • T = 292 K
  • Mean [sigma](C-C) = 0.007 Å
  • Disorder in main residue
  • R factor = 0.047
  • wR factor = 0.107
  • Data-to-parameter ratio = 7.2

checkCIF/PLATON results

No syntax errors found



Alert level B RINTA01_ALERT_3_B The value of Rint is greater than 0.15 Rint given 0.197
Author Response: Thin crystal (0.04 mm).
PLAT020_ALERT_3_B The value of Rint is greater than 0.10 .........       0.20
Author Response: Thin crystal (0.04 mm).

PLAT417_ALERT_2_B Short Inter D-H..H-D       H1WB   ..  H12     ..       2.09 Ang.
PLAT417_ALERT_2_B Short Inter D-H..H-D       H1WB   ..  H2WB    ..       1.87 Ang.
PLAT417_ALERT_2_B Short Inter D-H..H-D       H2WB   ..  H11     ..       2.05 Ang.

Alert level C PLAT041_ALERT_1_C Calc. and Rep. SumFormula Strings Differ .... ? PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ? PLAT045_ALERT_1_C Calculated and Reported Z Differ by ............ 0.50 Ratio PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ? PLAT089_ALERT_3_C Poor Data / Parameter Ratio (Zmax .LT. 18) ..... 7.16 PLAT152_ALERT_1_C Supplied and Calc Volume s.u. Inconsistent ..... ? PLAT301_ALERT_3_C Main Residue Disorder ......................... 2.00 Perc. PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 7 PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........ 4 PLAT731_ALERT_1_C Bond Calc 0.82(3), Rep 0.823(10) ...... 3.00 su-Rat O1W -H1WA 1.555 1.555 PLAT731_ALERT_1_C Bond Calc 0.82(4), Rep 0.826(10) ...... 4.00 su-Rat O1W -H1WB 1.555 1.555 PLAT732_ALERT_1_C Angle Calc 108(4), Rep 108.5(18) ...... 2.22 su-Rat H1WA -O1W -H1WB 1.555 1.555 1.555 PLAT735_ALERT_1_C D-H Calc 0.82(3), Rep 0.823(10) ...... 3.00 su-Rat O1W -H1# 1.555 1.555 PLAT735_ALERT_1_C D-H Calc 0.82(4), Rep 0.826(10) ...... 4.00 su-Rat O1W -H2# 1.555 1.555
Alert level G REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is correct. If it is not, please give the correct count in the _publ_section_exptl_refinement section of the submitted CIF. From the CIF: _diffrn_reflns_theta_max 25.00 From the CIF: _reflns_number_total 1447 Count of symmetry unique reflns 1449 Completeness (_total/calc) 99.86% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 0 Fraction of Friedel pairs measured 0.000 Are heavy atom types Z>Si present no
0 ALERT level A = In general: serious problem 5 ALERT level B = Potentially serious problem 14 ALERT level C = Check and explain 1 ALERT level G = General alerts; check 10 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 3 ALERT type 2 Indicator that the structure model may be wrong or deficient 5 ALERT type 3 Indicator that the structure quality may be low 2 ALERT type 4 Improvement, methodology, query or suggestion

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.

2,6-Dimethylpyridinium hydrogen (2R,3R)-(+)-tartrate sesquihydrate top
Crystal data top
C7H10N+·C4H5O6·1.5H2OF(000) = 604
Mr = 284.27Dx = 1.346 Mg m3
Orthorhombic, P212121Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2abCell parameters from 1276 reflections
a = 7.2094 (11) Åθ = 2.6–18.4°
b = 12.4483 (18) ŵ = 0.11 mm1
c = 15.628 (2) ÅT = 292 K
V = 1402.5 (4) Å3Plate, colourless
Z = 40.36 × 0.10 × 0.04 mm
Data collection top
Bruker SMART APEX CCD area-detector
diffractometer
1447 independent reflections
Radiation source: fine-focus sealed tube901 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.197
0.3° wide ω exposures scansθmax = 25.0°, θmin = 2.1°
Absorption correction: multi-scan
(SADABS; Bruker, 2001)
h = 88
Tmin = 0.960, Tmax = 0.995k = 1414
13627 measured reflectionsl = 1818
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)] = 0.047Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.107H atoms treated by a mixture of independent and constrained refinement
S = 0.90 w = 1/[σ2(Fo2) + (0.0424P)2]
where P = (Fo2 + 2Fc2)/3
1447 reflections(Δ/σ)max = 0.022
202 parametersΔρmax = 0.21 e Å3
36 restraintsΔρmin = 0.31 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.

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*/UeqOcc. (<1)
C10.1861 (7)0.3802 (3)0.5984 (3)0.0501 (11)
C20.1871 (7)0.2783 (4)0.6322 (3)0.0675 (15)
H20.18590.26870.69120.081*
C30.1899 (8)0.1905 (4)0.5785 (5)0.0770 (16)
H30.18850.12170.60160.092*
C40.1946 (9)0.2034 (4)0.4921 (4)0.0772 (17)
H40.19720.14340.45670.093*
C50.1957 (7)0.3039 (4)0.4569 (4)0.0621 (14)
C60.1765 (7)0.4815 (3)0.6471 (3)0.0619 (14)
H6A0.27740.52740.63060.093*
H6B0.18480.46630.70720.093*
H6C0.06090.51690.63530.093*
C70.1989 (9)0.3301 (4)0.3633 (3)0.0820 (17)
H7A0.22770.26640.33120.123*
H7B0.29150.38380.35250.123*
H7C0.07960.35670.34620.123*
C80.2100 (6)0.8288 (4)0.6707 (3)0.0454 (11)
C90.4180 (6)0.8221 (4)0.6707 (3)0.0418 (10)
H90.45360.74800.68430.050*
C100.4942 (5)0.8498 (3)0.5817 (3)0.0372 (10)
H100.44550.79760.54050.045*
C110.7078 (6)0.8425 (4)0.5816 (3)0.0409 (10)
N10.1910 (5)0.3880 (3)0.5111 (2)0.0494 (9)
H130.19120.45140.48920.059*
O10.1324 (4)0.7569 (2)0.62160 (19)0.0501 (8)
H10.02040.75580.63060.075*
O20.1255 (5)0.8946 (3)0.7120 (2)0.0761 (11)
O30.4940 (5)0.8900 (3)0.7331 (2)0.0714 (10)
H110.42330.94040.74170.107*
O40.4381 (4)0.9532 (2)0.5564 (2)0.0515 (8)
H120.34440.94870.52690.077*
O50.7774 (4)0.7570 (2)0.61074 (19)0.0526 (8)
O60.7971 (4)0.9187 (2)0.5509 (2)0.0527 (8)
O1W0.1278 (5)0.9403 (2)0.4595 (3)0.0692 (10)
H1WA0.039 (4)0.918 (3)0.487 (2)0.076 (6)*
H1WB0.169 (6)0.890 (2)0.431 (3)0.075 (6)*
O2W0.2992 (16)0.0827 (9)0.7704 (7)0.140 (3)0.50
H2WB0.317 (15)0.058 (9)0.819 (3)0.140 (3)*0.50
H2WA0.193 (7)0.065 (9)0.755 (7)0.140 (3)*0.50
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.040 (3)0.050 (3)0.060 (3)0.000 (2)0.002 (2)0.005 (2)
C20.052 (3)0.062 (3)0.089 (4)0.006 (3)0.004 (3)0.019 (3)
C30.068 (4)0.042 (3)0.121 (5)0.003 (3)0.001 (4)0.013 (3)
C40.072 (4)0.049 (4)0.111 (5)0.003 (3)0.000 (4)0.023 (3)
C50.047 (3)0.053 (3)0.087 (4)0.012 (3)0.005 (3)0.019 (3)
C60.074 (4)0.054 (3)0.057 (3)0.003 (3)0.001 (3)0.004 (2)
C70.093 (4)0.093 (4)0.060 (4)0.021 (4)0.009 (3)0.027 (3)
C80.033 (3)0.058 (3)0.045 (3)0.001 (3)0.003 (2)0.006 (2)
C90.031 (3)0.050 (2)0.045 (3)0.002 (2)0.000 (2)0.000 (2)
C100.026 (2)0.040 (2)0.045 (3)0.0056 (18)0.0012 (18)0.0015 (19)
C110.030 (2)0.050 (3)0.043 (2)0.002 (2)0.001 (2)0.002 (2)
N10.045 (2)0.038 (2)0.066 (3)0.005 (2)0.002 (2)0.0003 (19)
O10.0280 (16)0.0509 (18)0.071 (2)0.0007 (15)0.0037 (15)0.0001 (17)
O20.050 (2)0.098 (3)0.080 (2)0.013 (2)0.0067 (18)0.035 (2)
O30.056 (2)0.103 (3)0.055 (2)0.0135 (19)0.0035 (18)0.019 (2)
O40.0334 (17)0.0466 (17)0.074 (2)0.0002 (14)0.0071 (16)0.0116 (16)
O50.0319 (17)0.0475 (18)0.078 (2)0.0051 (15)0.0025 (16)0.0092 (18)
O60.0318 (16)0.0539 (18)0.072 (2)0.0034 (15)0.0019 (16)0.0141 (17)
O1W0.048 (2)0.062 (2)0.098 (3)0.0030 (17)0.0049 (18)0.014 (2)
O2W0.140 (3)0.140 (3)0.140 (3)0.0001 (6)0.0003 (6)0.0001 (6)
Geometric parameters (Å, º) top
C1—N11.367 (5)C8—O11.305 (5)
C1—C21.374 (6)C8—C91.502 (6)
C1—C61.476 (6)C9—O31.401 (5)
C2—C31.378 (7)C9—C101.534 (6)
C2—H20.9300C9—H90.9800
C3—C41.360 (8)C10—O41.406 (4)
C3—H30.9300C10—C111.542 (6)
C4—C51.366 (7)C10—H100.9800
C4—H40.9300C11—O61.242 (5)
C5—N11.348 (5)C11—O51.262 (4)
C5—C71.499 (7)N1—H130.8600
C6—H6A0.9600O1—H10.8200
C6—H6B0.9600O3—H110.8200
C6—H6C0.9600O4—H120.8200
C7—H7A0.9600O1W—H1WA0.823 (10)
C7—H7B0.9600O1W—H1WB0.826 (10)
C7—H7C0.9600O2W—H2WB0.831 (11)
C8—O21.208 (5)O2W—H2WA0.830 (11)
N1—C1—C2116.7 (4)O2—C8—O1124.3 (4)
N1—C1—C6117.1 (4)O2—C8—C9122.8 (5)
C2—C1—C6126.2 (5)O1—C8—C9112.9 (4)
C1—C2—C3119.8 (5)O3—C9—C8110.9 (4)
C1—C2—H2120.1O3—C9—C10110.8 (3)
C3—C2—H2120.1C8—C9—C10110.2 (4)
C4—C3—C2120.8 (5)O3—C9—H9108.3
C4—C3—H3119.6C8—C9—H9108.3
C2—C3—H3119.6C10—C9—H9108.3
C3—C4—C5120.5 (5)O4—C10—C9111.0 (3)
C3—C4—H4119.7O4—C10—C11109.9 (3)
C5—C4—H4119.7C9—C10—C11110.2 (3)
N1—C5—C4117.3 (5)O4—C10—H10108.6
N1—C5—C7116.4 (4)C9—C10—H10108.6
C4—C5—C7126.3 (5)C11—C10—H10108.6
C1—C6—H6A109.5O6—C11—O5125.2 (4)
C1—C6—H6B109.5O6—C11—C10118.2 (4)
H6A—C6—H6B109.5O5—C11—C10116.5 (4)
C1—C6—H6C109.5C5—N1—C1124.9 (4)
H6A—C6—H6C109.5C5—N1—H13117.6
H6B—C6—H6C109.5C1—N1—H13117.6
C5—C7—H7A109.5C8—O1—H1109.5
C5—C7—H7B109.5C9—O3—H11109.5
H7A—C7—H7B109.5C10—O4—H12109.5
C5—C7—H7C109.5H1WA—O1W—H1WB108.5 (18)
H7A—C7—H7C109.5H2WB—O2W—H2WA108.1 (19)
H7B—C7—H7C109.5
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H13···O6i0.861.902.705 (4)156
N1—H13···O4i0.862.292.889 (4)127
O1—H1···O5ii0.821.782.565 (4)160
O3—H11···O2Wiii0.822.032.840 (13)168
O3—H11···O20.822.272.677 (5)111
O4—H12···O1W0.821.892.706 (5)179
O1W—H1WA···O6ii0.82 (1)2.01 (2)2.792 (5)160 (4)
O1W—H1WB···O5i0.83 (1)2.09 (2)2.899 (4)165 (5)
O2W—H2WB···O1Wiv0.83 (1)2.23 (5)3.016 (12)158 (12)
O2W—H2WA···O2v0.83 (1)2.28 (11)2.807 (12)122 (10)
O3—H11···O20.822.272.677 (5)111
Symmetry codes: (i) x1/2, y+3/2, z+1; (ii) x1, y, z; (iii) x, y+1, z; (iv) x+1/2, y+1, z+1/2; (v) x, y1, z.
 

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