2,2′:6′,2′′-Ter­pyridine 1,1′′-dioxide dihydrate

The title compound, C₁₅H₁₁N₃O₃·2H₂O, crystallizes with ter­pyridine dioxide mol­ecules positioned on mirror planes in the space group Pnma. Catemeric assemblages of ter­pyridine mol­ecules [C—H...⁻O—⁺N = 3.386 (4) Å] are linked by bridging water mol­ecules [C—H...O = 3.288 (4) and 3.386 (4) Å; O—H...⁻O—⁺N = 2.837 (3) and 2.878 (4) Å], giving stacks of two-dimensional undulating motifs.

Key indicators

• Single-crystal X-ray study
• T = 298 K
• Mean [sigma](C-C) = 0.004 Å
• R factor = 0.052
• wR factor = 0.156
• Data-to-parameter ratio = 9.7

checkCIF/PLATON results

No syntax errors found



Alert level A
PLAT725_ALERT_1_A D-H     Calc     0.91(3), Rep     1.08000 Dev...       0.17 Ang.
              C1   -H1      1.555   1.555

Author Response: ...see _publ_section_exptl_refinement

PLAT725_ALERT_1_A D-H     Calc     0.88(3), Rep     1.08000 Dev...       0.20 Ang.
              C2   -H2      1.555   1.555

Author Response: ...see _publ_section_exptl_refinement

PLAT725_ALERT_1_A D-H     Calc     0.91(3), Rep     1.08000 Dev...       0.17 Ang.
              C3   -H3      1.555   1.555

Author Response: ...see _publ_section_exptl_refinement

PLAT726_ALERT_1_A H...A   Calc     2.57(3), Rep     2.46000 Dev...       0.11 Ang.
              H1   -O2      1.555   5.766

Author Response: ...see _publ_section_exptl_refinement

PLAT726_ALERT_1_A H...A   Calc     2.75(3), Rep     2.63000 Dev...       0.12 Ang.
              H2   -O2      1.555   5.766

Author Response: ...see _publ_section_exptl_refinement

PLAT726_ALERT_1_A H...A   Calc     2.51(3), Rep     2.34000 Dev...       0.17 Ang.
              H3   -O1      1.555   1.556

Author Response: ...see _publ_section_exptl_refinement

Alert level C
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ ....          ?
PLAT088_ALERT_3_C Poor Data / Parameter Ratio ....................       9.72
PLAT355_ALERT_3_C Long    O-H Bond (0.82A)   O2     -   H9     ...       1.01 Ang.
PLAT355_ALERT_3_C Long    O-H Bond (0.82A)   O2     -   H10    ...       1.01 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H2     ..  O2      ..       2.63 Ang.
PLAT707_ALERT_1_C D...A   Calc    3.183(4), Rep    3.178(4), Dev..       1.25 Sigma
              C1   -O2      1.555   5.766
PLAT707_ALERT_1_C D...A   Calc    3.391(3), Rep    3.386(4), Dev..       1.67 Sigma
              C3   -O1      1.555   1.556
PLAT728_ALERT_1_C D-H..A  Calc      125(2), Rep      123.00 Dev...       2.00 Deg.
              C1   -H1   -O2      1.555   1.555   5.766
PLAT728_ALERT_1_C D-H..A  Calc      121(2), Rep      119.00 Dev...       2.00 Deg.
              C2   -H2   -O2      1.555   1.555   5.766
PLAT731_ALERT_1_C Bond    Calc     1.01(5), Rep     1.01(2) ......       2.50 su-Rat
              O2   -H9      1.555   1.555
PLAT731_ALERT_1_C Bond    Calc     1.01(5), Rep     1.01(2) ......       2.50 su-Rat
              O2   -H10     1.555   1.555
PLAT735_ALERT_1_C D-H     Calc     1.01(5), Rep     1.01(2) ......       2.50 su-Rat
              O2   -H9      1.555   1.555
PLAT735_ALERT_1_C D-H     Calc     1.01(5), Rep     1.01(2) ......       2.50 su-Rat
              O2   -H10     1.555   1.555
PLAT736_ALERT_1_C H...A   Calc     1.84(5), Rep     1.83(2) ......       2.50 su-Rat
              H9   -O1      1.555   1.555
PLAT745_ALERT_1_C D-H     Calc     0.91(3), Rep     1.08000 ......    Missing su
              C1   -H1      1.555   1.555
PLAT745_ALERT_1_C D-H     Calc     0.88(3), Rep     1.08000 ......    Missing su
              C2   -H2      1.555   1.555
PLAT745_ALERT_1_C D-H     Calc     0.91(3), Rep     1.08000 ......    Missing su
              C3   -H3      1.555   1.555
PLAT746_ALERT_1_C H...A   Calc     2.57(3), Rep     2.46000 ......    Missing su
              H1   -O2      1.555   5.766
PLAT746_ALERT_1_C H...A   Calc     2.75(3), Rep     2.63000 ......    Missing su
              H2   -O2      1.555   5.766
PLAT746_ALERT_1_C H...A   Calc     2.51(3), Rep     2.34000 ......    Missing su
              H3   -O1      1.555   1.556

   6 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
  20 ALERT level C = Check and explain
   0 ALERT level G = General alerts; check

  22 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   0 ALERT type 2 Indicator that the structure model may be wrong or deficient
   3 ALERT type 3 Indicator that the structure quality may be low
   1 ALERT type 4 Improvement, methodology, query or suggestion

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Computing details

Data collection: XSCANS (Bruker, 1999); cell refinement: XSCANS; data reduction: XSCANS; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: X-SEED (Barbour, 2001); software used to prepare material for publication: X-SEED.

2,2':6',2''-Terpyridine 1,1''-dioxide dihydrate

Crystal data

C15H11N3O2·2H2O	F(000) = 632
Mr = 301.30	Dx = 1.435 Mg m^−3
Orthorhombic, Pnma	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2n	Cell parameters from 22 reflections
a = 7.2590 (6) Å	θ = 23.5–26.8°
b = 25.872 (3) Å	µ = 0.11 mm^−1
c = 7.4250 (15) Å	T = 298 K
V = 1394.5 (3) Å^3	Transparent plate, colorless
Z = 4	0.42 × 0.36 × 0.10 mm

Data collection

Siemens P4 diffractometer	Rint = 0.024
Radiation source: fine-focus sealed tube	θmax = 25.4°, θmin = 2.9°
Graphite monochromator	h = −8→1
θ/2θ scans	k = −1→31
1830 measured reflections	l = −1→8
1302 independent reflections	3 standard reflections every 97 reflections
868 reflections with I > 2σ(I)	intensity decay: <3%

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.052	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.156	H atoms treated by a mixture of independent and constrained refinement
S = 1.06	w = 1/[σ^2(Fo^2) + (0.0881P)^2] where P = (Fo^2 + 2Fc^2)/3
1302 reflections	(Δ/σ)max < 0.001
134 parameters	Δρmax = 0.18 e Å^−3
2 restraints	Δρmin = −0.23 e Å^−3

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
O1	0.7717 (3)	0.38951 (7)	0.3949 (2)	0.0510 (6)
O2	1.0139 (4)	0.46391 (10)	0.2452 (4)	0.0747 (8)
N1	0.7551 (3)	0.38574 (8)	0.5712 (3)	0.0352 (6)
N2	0.6973 (4)	0.2500	0.6188 (4)	0.0315 (7)
C1	0.7991 (4)	0.42728 (11)	0.6739 (4)	0.0425 (7)
C2	0.7891 (4)	0.42533 (12)	0.8576 (4)	0.0447 (8)
C3	0.7341 (4)	0.38046 (11)	0.9408 (4)	0.0443 (7)
C4	0.6897 (4)	0.33842 (11)	0.8357 (4)	0.0385 (7)
C5	0.7000 (3)	0.34040 (9)	0.6484 (3)	0.0312 (6)
C6	0.6546 (3)	0.29476 (9)	0.5378 (3)	0.0308 (6)
C7	0.5668 (4)	0.29625 (11)	0.3710 (4)	0.0363 (7)
C8	0.5221 (5)	0.2500	0.2901 (5)	0.0361 (9)
H1	0.841 (4)	0.4554 (11)	0.612 (4)	0.051 (9)*
H2	0.825 (4)	0.4524 (12)	0.921 (4)	0.057 (9)*
H3	0.721 (4)	0.3790 (11)	1.062 (4)	0.050 (9)*
H4	0.647 (4)	0.3088 (11)	0.884 (4)	0.039 (7)*
H7	0.538 (4)	0.3253 (12)	0.318 (4)	0.038 (8)*
H8	0.459 (5)	0.2500	0.172 (5)	0.035 (10)*
H9	0.941 (7)	0.4358 (17)	0.307 (7)	0.16 (2)*
H10	1.097 (8)	0.4380 (19)	0.183 (7)	0.16 (2)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0737 (14)	0.0468 (12)	0.0325 (10)	−0.0149 (11)	0.0008 (9)	0.0064 (9)
O2	0.0902 (19)	0.0542 (14)	0.0796 (19)	−0.0127 (14)	0.0090 (16)	0.0009 (15)
N1	0.0384 (12)	0.0345 (11)	0.0328 (11)	−0.0002 (10)	−0.0023 (9)	0.0008 (10)
N2	0.0321 (15)	0.0327 (16)	0.0296 (15)	0.000	0.0003 (13)	0.000
C1	0.0477 (17)	0.0323 (15)	0.0474 (17)	−0.0038 (13)	−0.0027 (14)	0.0008 (13)
C2	0.0476 (17)	0.0398 (16)	0.0467 (17)	0.0017 (13)	−0.0054 (14)	−0.0139 (14)
C3	0.0504 (16)	0.0507 (17)	0.0317 (15)	0.0058 (14)	−0.0003 (13)	−0.0058 (13)
C4	0.0449 (16)	0.0360 (15)	0.0345 (14)	0.0018 (12)	0.0024 (12)	0.0007 (13)
C5	0.0303 (13)	0.0325 (14)	0.0307 (13)	0.0028 (10)	−0.0002 (11)	0.0013 (11)
C6	0.0288 (12)	0.0331 (13)	0.0305 (13)	0.0025 (11)	0.0026 (11)	0.0021 (11)
C7	0.0381 (13)	0.0365 (15)	0.0345 (15)	0.0036 (12)	−0.0018 (12)	0.0059 (13)
C8	0.0349 (19)	0.044 (2)	0.029 (2)	0.000	−0.0064 (16)	0.000

Geometric parameters (Å, º)

O1—N1	1.318 (3)	C3—C4	1.377 (4)
O2—H9	1.01 (2)	C3—H3	0.91 (3)
O2—H10	1.01 (2)	C4—C5	1.394 (4)
N1—C1	1.356 (3)	C4—H4	0.90 (3)
N1—C5	1.365 (3)	C5—C6	1.476 (3)
N2—C6^i	1.341 (3)	C6—C7	1.394 (4)
N2—C6	1.341 (3)	C7—C8	1.378 (3)
C1—C2	1.367 (4)	C7—H7	0.87 (3)
C1—H1	0.91 (3)	C8—C7^i	1.378 (3)
C2—C3	1.374 (4)	C8—H8	0.99 (4)
C2—H2	0.88 (3)
H9—O2—H10	92 (4)	C3—C4—H4	121.6 (17)
O1—N1—C1	118.6 (2)	C5—C4—H4	116.7 (17)
O1—N1—C5	120.5 (2)	N1—C5—C4	117.8 (2)
C1—N1—C5	120.9 (2)	N1—C5—C6	121.3 (2)
C6^i—N2—C6	119.4 (3)	C4—C5—C6	120.9 (2)
N1—C1—C2	121.3 (3)	N2—C6—C7	121.9 (2)
N1—C1—H1	115.5 (18)	N2—C6—C5	112.9 (2)
C2—C1—H1	123.2 (18)	C7—C6—C5	125.1 (2)
C1—C2—C3	119.7 (3)	C8—C7—C6	118.1 (3)
C1—C2—H2	119 (2)	C8—C7—H7	119.9 (18)
C3—C2—H2	121 (2)	C6—C7—H7	122.0 (18)
C2—C3—C4	118.7 (3)	C7—C8—C7^i	120.6 (3)
C2—C3—H3	120.7 (19)	C7—C8—H8	119.70 (17)
C4—C3—H3	120.5 (19)	C7^i—C8—H8	119.70 (17)
C3—C4—C5	121.6 (3)
O1—N1—C1—C2	−178.4 (3)	C3—C4—C5—C6	179.1 (2)
C5—N1—C1—C2	−0.3 (4)	C6^i—N2—C6—C7	0.0 (4)
N1—C1—C2—C3	0.3 (4)	C6^i—N2—C6—C5	176.50 (19)
C1—C2—C3—C4	−0.2 (4)	N1—C5—C6—N2	147.0 (2)
C2—C3—C4—C5	0.2 (4)	C4—C5—C6—N2	−32.4 (3)
O1—N1—C5—C4	178.3 (2)	N1—C5—C6—C7	−36.6 (3)
C1—N1—C5—C4	0.3 (4)	C4—C5—C6—C7	144.0 (3)
O1—N1—C5—C6	−1.0 (4)	N2—C6—C7—C8	0.6 (4)
C1—N1—C5—C6	−179.0 (2)	C5—C6—C7—C8	−175.4 (3)
C3—C4—C5—N1	−0.3 (4)	C6—C7—C8—C7^i	−1.3 (5)

Symmetry code: (i) x, −y+1/2, z.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O2—H9···O1	1.01 (2)	1.83 (2)	2.837 (3)	174 (6)
O2—H10···O1^ii	1.01 (2)	1.89 (3)	2.878 (4)	168 (7)
C1—H1···O2^iii	1.08	2.46	3.178 (4)	123
C2—H2···O2^iii	1.08	2.63	3.288 (4)	119
C3—H3···O1^iv	1.08	2.34	3.386 (4)	162

Symmetry codes: (ii) x+1/2, y, −z+1/2; (iii) −x+2, −y+1, −z+1; (iv) x, y, z+1.