2,2′:6′,2′′-Ter­pyridine N,N′,N′′-trioxide

The title compound, C₁₅H₁₁N₃O₃, crystallizes with mol­ecules positioned on twofold rotation axes in space group P4₃2₁2. Five crystallographically unique intermolecular C—H...⁻O—⁺N contacts with H...O = 2.201 (7), 2.50 (2), 2.45 (1), 2.38 (1) and 2.35 (2) Å produce a complex network of hydrogen bonds that assist in the stabilization of the crystal structure.

Key indicators

• Single-crystal X-ray study
• T = 213 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.033
• wR factor = 0.082
• Data-to-parameter ratio = 11.9

checkCIF/PLATON results

No syntax errors found



Alert level A
PLAT706_ALERT_1_A H...A   Calc     2.28(2), Rep    2.201(7), Dev..       3.95 Sigma
              H1   -O1      1.555   2.544

Author Response: Reported C-H distances have been normalized to 1.08 (see Experimental)

PLAT706_ALERT_1_A H...A   Calc     2.61(2), Rep     2.50(2), Dev..       5.50 Sigma
              H2   -O1      1.555   6.654

Author Response: Reported C-H distances have been normalized to 1.08 (see Experimental)

PLAT706_ALERT_1_A H...A   Calc     2.57(2), Rep   2.450(10), Dev..       6.00 Sigma
              H3   -O1      1.555   7.655

Author Response: Reported C-H distances have been normalized to 1.08 (see Experimental)

PLAT706_ALERT_1_A H...A   Calc     2.48(2), Rep   2.380(10), Dev..       5.00 Sigma
              H4   -O1      1.555   5.555

Author Response: Reported C-H distances have been normalized to 1.08 (see Experimental)

PLAT725_ALERT_1_A D-H     Calc     0.99(2), Rep     1.08000 Dev...       0.09 Ang.
              C1   -H1      1.555   1.555

Author Response: Reported C-H distances have been normalized to 1.08 (see Experimental)

PLAT725_ALERT_1_A D-H     Calc     0.94(2), Rep     1.08000 Dev...       0.14 Ang.
              C2   -H2      1.555   1.555

Author Response: Reported C-H distances have been normalized to 1.08 (see Experimental)

PLAT725_ALERT_1_A D-H     Calc     0.94(2), Rep     1.08000 Dev...       0.14 Ang.
              C3   -H3      1.555   1.555

Author Response: Reported C-H distances have been normalized to 1.08 (see Experimental)

PLAT725_ALERT_1_A D-H     Calc     0.96(3), Rep     1.08000 Dev...       0.12 Ang.
              C4   -H4      1.555   1.555

Author Response: Reported C-H distances have been normalized to 1.08 (see Experimental)

PLAT725_ALERT_1_A D-H     Calc     0.96(3), Rep     1.08000 Dev...       0.12 Ang.
              C4   -H4      1.555   1.555

Author Response: Reported C-H distances have been normalized to 1.08 (see Experimental)

Alert level B
PLAT706_ALERT_1_B H...A   Calc     2.43(3), Rep     2.35(2), Dev..       2.67 Sigma
              H4   -O2      1.555   5.555

Author Response: Reported C-H distances have been normalized to 1.08 (see Experimental)

Alert level C
PLAT708_ALERT_1_C D-H..A  Calc   162.7(17), Rep   160.2(16), Dev..       1.47 Sigma
              C1   -H1   -O1      1.555   1.555   2.544
PLAT708_ALERT_1_C D-H..A  Calc   138.5(16), Rep   136.7(17), Dev..       1.13 Sigma
              C2   -H2   -O1      1.555   1.555   6.654
PLAT732_ALERT_1_C Angle   Calc    120.8(3), Rep  120.80(13) ......       2.31 su-Rat
              C7   -C8   -H8      1.555   1.555   1.555
PLAT733_ALERT_1_C Torsion Calc     -2.2(3), Rep   -2.15(13) ......       2.31 su-Rat
              C6  -N2  -C6  -C7     8.665   1.555   1.555   1.555
PLAT733_ALERT_1_C Torsion Calc     -2.2(3), Rep   -2.16(13) ......       2.31 su-Rat
              C6  -C7  -C8  -C7     1.555   1.555   1.555   8.665
PLAT736_ALERT_1_C H...A   Calc     2.28(2), Rep    2.201(7) ......       2.86 su-Rat
              H1   -O1      1.555   2.544
PLAT745_ALERT_1_C D-H     Calc     0.99(2), Rep     1.08000 ......    Missing su
              C1   -H1      1.555   1.555
PLAT745_ALERT_1_C D-H     Calc     0.94(2), Rep     1.08000 ......    Missing su
              C2   -H2      1.555   1.555
PLAT745_ALERT_1_C D-H     Calc     0.94(2), Rep     1.08000 ......    Missing su
              C3   -H3      1.555   1.555
PLAT745_ALERT_1_C D-H     Calc     0.96(3), Rep     1.08000 ......    Missing su
              C4   -H4      1.555   1.555
PLAT745_ALERT_1_C D-H     Calc     0.96(3), Rep     1.08000 ......    Missing su
              C4   -H4      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           27.41
           From the CIF: _reflns_number_total                875
           Count of symmetry unique reflns          875
           Completeness (_total/calc)            100.00%
           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

   9 ALERT level A = In general: serious problem
   1 ALERT level B = Potentially serious problem
  11 ALERT level C = Check and explain
   1 ALERT level G = General alerts; check

  21 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
   0 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: SMART (Bruker, 2001); cell refinement: SMART; data reduction: SAINT (Bruker, 2002) and XPREP (Bruker, 2001); program(s) used to solve structure: SHELXTL (Bruker, 2000); program(s) used to refine structure: SHELXTL; molecular graphics: X-SEED (Barbour, 2001); software used to prepare material for publication: X-SEED.

2,2':6',2''-Terpyridine N,N',N''-trioxide

Crystal data

C15H11N3O3	Dx = 1.499 Mg m^−3
Mr = 281.27	Mo Kα radiation, λ = 0.71073 Å
Tetragonal, P43212	Cell parameters from 2341 reflections
Hall symbol: P 4nw 2abw	θ = 2.6–26.6°
a = 9.868 (1) Å	µ = 0.11 mm^−1
c = 12.801 (2) Å	T = 213 K
V = 1246.6 (3) Å^3	Prisms, colorless
Z = 4	0.20 × 0.20 × 0.10 mm
F(000) = 584

Data collection

Bruker P4 CCD area-detector diffractometer	1420 independent reflections
Radiation source: fine-focus sealed tube	1296 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.041
φ and ω scans	θmax = 27.4°, θmin = 2.6°
Absorption correction: multi-scan (SADABS; Bruker, 2000)	h = −12→12
Tmin = 0.961, Tmax = 0.985	k = −12→11
9375 measured reflections	l = −16→15

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)] = 0.033	Hydrogen site location: difference Fourier map
wR(F^2) = 0.082	All H-atom parameters refined
S = 1.07	w = 1/[σ^2(Fo^2) + (0.0507P)^2 + 0.1514P] where P = (Fo^2 + 2Fc^2)/3
1420 reflections	(Δ/σ)max < 0.001
119 parameters	Δρmax = 0.18 e Å^−3
0 restraints	Δρmin = −0.24 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.

Flack parameter refines to 2(2). Due to the lack of non-heavy atoms and stereogenic center, and use of Mo radiation, the choice of space group [P 4(3)2(1)2 or P 4(1)2(1)2] was ambiguous. Refinement implementing both space groups gave similar results (including flack parameters).

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
O1	0.68501 (14)	0.06773 (13)	0.05512 (10)	0.0315 (3)
O2	0.74878 (12)	0.25122 (12)	0.2500	0.0272 (4)
N1	0.75506 (15)	0.16938 (14)	0.01814 (10)	0.0232 (3)
N2	0.84108 (15)	0.15892 (15)	0.2500	0.0232 (4)
C1	0.7125 (2)	0.23496 (19)	−0.06913 (14)	0.0292 (4)
H1	0.626 (2)	0.202 (2)	−0.0987 (17)	0.036 (6)*
C2	0.7866 (2)	0.3403 (2)	−0.10967 (15)	0.0322 (5)
H2	0.751 (2)	0.379 (2)	−0.1706 (18)	0.040 (6)*
C3	0.9052 (2)	0.3820 (2)	−0.06207 (15)	0.0337 (5)
H3	0.956 (2)	0.454 (2)	−0.0890 (16)	0.027 (5)*
C4	0.94757 (19)	0.3147 (2)	0.02701 (14)	0.0284 (4)
H4	1.033 (3)	0.339 (2)	0.0582 (17)	0.044 (6)*
C5	0.87210 (17)	0.20897 (18)	0.06677 (13)	0.0232 (4)
C6	0.91146 (19)	0.13084 (18)	0.16027 (13)	0.0257 (4)
C7	1.0135 (2)	0.0351 (2)	0.16095 (15)	0.0334 (5)
H7	1.064 (2)	0.021 (2)	0.1004 (17)	0.036 (6)*
C8	1.0400 (2)	−0.0400 (2)	0.2500	0.0388 (7)
H8	1.112 (2)	−0.112 (2)	0.2500	0.033 (8)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0357 (8)	0.0279 (7)	0.0309 (6)	−0.0096 (6)	−0.0006 (6)	0.0048 (5)
O2	0.0271 (6)	0.0271 (6)	0.0274 (9)	0.0083 (8)	0.0001 (5)	0.0001 (5)
N1	0.0259 (7)	0.0231 (7)	0.0206 (7)	−0.0008 (6)	0.0012 (6)	−0.0010 (6)
N2	0.0247 (7)	0.0247 (7)	0.0204 (9)	0.0012 (8)	−0.0028 (6)	−0.0028 (6)
C1	0.0321 (10)	0.0330 (10)	0.0223 (9)	0.0010 (8)	−0.0045 (7)	0.0010 (7)
C2	0.0411 (12)	0.0319 (10)	0.0237 (9)	0.0048 (8)	0.0014 (8)	0.0054 (7)
C3	0.0377 (11)	0.0288 (10)	0.0346 (10)	−0.0021 (8)	0.0114 (8)	0.0017 (8)
C4	0.0240 (9)	0.0307 (10)	0.0305 (9)	−0.0016 (8)	0.0039 (7)	−0.0040 (8)
C5	0.0242 (9)	0.0268 (9)	0.0185 (7)	0.0034 (7)	0.0011 (6)	−0.0039 (7)
C6	0.0271 (9)	0.0298 (9)	0.0203 (8)	0.0013 (7)	−0.0025 (7)	−0.0045 (7)
C7	0.0323 (10)	0.0451 (12)	0.0227 (10)	0.0120 (9)	−0.0023 (8)	−0.0075 (8)
C8	0.0432 (11)	0.0432 (11)	0.0299 (14)	0.0192 (14)	−0.0055 (9)	−0.0055 (9)

Geometric parameters (Å, º)

O1—N1	1.3070 (19)	C3—C4	1.384 (3)
O2—N2	1.288 (3)	C3—H3	0.94 (2)
N1—C1	1.358 (2)	C4—C5	1.380 (3)
N1—C5	1.369 (2)	C4—H4	0.96 (2)
N2—C6	1.371 (2)	C5—C6	1.476 (2)
N2—C6^i	1.371 (2)	C6—C7	1.381 (3)
C1—C2	1.372 (3)	C7—C8	1.385 (2)
C1—H1	0.99 (2)	C7—H7	0.93 (2)
C2—C3	1.382 (3)	C8—C7^i	1.385 (2)
C2—H2	0.94 (2)	C8—H8	1.00 (3)
O1—N1—C1	120.03 (15)	C5—C4—C3	120.26 (17)
O1—N1—C5	120.04 (14)	C5—C4—H4	120.4 (14)
C1—N1—C5	119.93 (15)	C3—C4—H4	119.2 (14)
O2—N2—C6	120.08 (10)	N1—C5—C4	120.24 (16)
O2—N2—C6^i	120.08 (10)	N1—C5—C6	116.22 (16)
C6—N2—C6^i	119.8 (2)	C4—C5—C6	123.53 (16)
N1—C1—C2	120.50 (17)	N2—C6—C7	120.17 (17)
N1—C1—H1	115.1 (13)	N2—C6—C5	116.15 (15)
C2—C1—H1	124.4 (13)	C7—C6—C5	123.68 (16)
C1—C2—C3	120.67 (18)	C6—C7—C8	120.61 (19)
C1—C2—H2	115.4 (14)	C6—C7—H7	119.1 (13)
C3—C2—H2	123.9 (15)	C8—C7—H7	120.3 (13)
C2—C3—C4	118.40 (19)	C7—C8—C7^i	118.4 (3)
C2—C3—H3	121.2 (13)	C7—C8—H8	120.80 (13)
C4—C3—H3	120.4 (13)	C7^i—C8—H8	120.80 (13)
O1—N1—C1—C2	−178.84 (16)	O2—N2—C6—C7	177.85 (13)
C5—N1—C1—C2	0.5 (3)	C6^i—N2—C6—C7	−2.15 (13)
N1—C1—C2—C3	−0.4 (3)	O2—N2—C6—C5	−1.55 (18)
C1—C2—C3—C4	0.3 (3)	C6^i—N2—C6—C5	178.45 (18)
C2—C3—C4—C5	−0.2 (3)	N1—C5—C6—N2	−76.84 (18)
O1—N1—C5—C4	178.90 (16)	C4—C5—C6—N2	104.43 (19)
C1—N1—C5—C4	−0.4 (2)	N1—C5—C6—C7	103.8 (2)
O1—N1—C5—C6	0.1 (2)	C4—C5—C6—C7	−74.9 (2)
C1—N1—C5—C6	−179.23 (16)	N2—C6—C7—C8	4.3 (3)
C3—C4—C5—N1	0.3 (3)	C5—C6—C7—C8	−176.30 (16)
C3—C4—C5—C6	179.00 (16)	C6—C7—C8—C7^i	−2.16 (13)

Symmetry code: (i) −y+1, −x+1, −z+1/2.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C1—H1···O1^ii	1.08	2.201 (7)	3.238 (2)	160.2 (16)
C2—H2···O1^iii	1.08	2.50 (2)	3.373 (2)	136.7 (17)
C3—H3···O1^iv	1.08	2.45 (1)	3.395 (2)	146.1 (14)
C4—H4···O1^v	1.08	2.38 (1)	3.383 (2)	154.2 (17)
C4—H4···O2^v	1.08	2.35 (2)	3.061 (2)	122.1 (15)

Symmetry codes: (ii) −y+1/2, x−1/2, z−1/4; (iii) −x+3/2, y+1/2, −z−1/4; (iv) y+1, x, −z; (v) x+1/2, −y+1/2, −z+1/4.