2,6-Bis­[bis(2-pyridyl)­hydroxy­methyl]­pyridine

The crystal structure of the title compound, 2,6-bis­[bis(2-pyridyl)­hydroxy­methyl]­pyridine, C₂₇H₂₁N₅O₂, at 180 K contains intramolecular O—H...N contacts. In space group C2/c, the mol­ecule is sited on a twofold axis.

Key indicators

• Single-crystal X-ray study
• T = 180 K
• Mean [sigma](C-C) = 0.002 Å
• R factor = 0.036
• wR factor = 0.095
• Data-to-parameter ratio = 13.5

checkCIF/PLATON results

No syntax errors found



Alert level C
ABSTM02_ALERT_3_C  The ratio of expected to reported Tmax/Tmin(RR') is < 0.90
            Tmin and Tmax reported:      0.877     0.989
            Tmin' and Tmax expected:      0.977     0.989
            RR' =      0.898
            Please check that your absorption correction is appropriate.
PLAT061_ALERT_3_C Tmax/Tmin Range Test RR' too Large .............       0.90

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

   0 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
   2 ALERT type 3 Indicator that the structure quality may be low
   0 ALERT type 4 Improvement, methodology, query or suggestion

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Computing details

Data collection: APEX2 (Bruker–Nonius, 2003); cell refinement: SAINT (Bruker, 2003); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2000); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

2,6-bis[bis(2-pyridyl)hydroxymethyl]pyridine

Crystal data

C27H21N5O2	F(000) = 936
Mr = 447.49	Dx = 1.392 Mg m^−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 2609 reflections
a = 15.0847 (12) Å	θ = 2.7–26.4°
b = 7.6587 (6) Å	µ = 0.09 mm^−1
c = 18.4907 (15) Å	T = 180 K
β = 92.216 (1)°	Block, yellow
V = 2134.6 (3) Å^3	0.25 × 0.15 × 0.12 mm
Z = 4

Data collection

Bruker–Nonius X8APEX-II CCD diffractometer	2142 independent reflections
Radiation source: fine-focus sealed tube	1754 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.022
Thin–slice ω and φ scans	θmax = 26.4°, θmin = 3.6°
Absorption correction: multi-scan (SADABS; Sheldrick, 2003)	h = −18→18
Tmin = 0.877, Tmax = 0.989	k = −9→9
6383 measured reflections	l = −23→18

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)] = 0.036	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.095	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	w = 1/[σ^2(Fo^2) + (0.0435P)^2 + 1.2461P] where P = (Fo^2 + 2Fc^2)/3
2142 reflections	(Δ/σ)max < 0.001
159 parameters	Δρmax = 0.23 e Å^−3
0 restraints	Δρmin = −0.15 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	0.61086 (7)	0.08213 (13)	0.42237 (5)	0.0354 (3)
H1	0.6622 (15)	0.130 (3)	0.4367 (11)	0.079 (7)*
N1	0.5000	0.17985 (19)	0.2500	0.0258 (3)
N2	0.71972 (7)	0.32585 (15)	0.39605 (6)	0.0323 (3)
N3	0.47672 (8)	0.45330 (15)	0.36886 (6)	0.0354 (3)
C1	0.5000	−0.1804 (3)	0.2500	0.0410 (5)
H1A	0.5000	−0.3045	0.2500	0.049*
C2	0.53986 (9)	−0.09033 (18)	0.30715 (8)	0.0359 (3)
H2A	0.5678	−0.1507	0.3467	0.043*
C3	0.53805 (8)	0.09106 (16)	0.30532 (7)	0.0274 (3)
C4	0.57631 (8)	0.19950 (16)	0.36920 (7)	0.0281 (3)
C5	0.49983 (8)	0.30459 (17)	0.40159 (7)	0.0278 (3)
C6	0.45738 (9)	0.2420 (2)	0.46155 (8)	0.0363 (3)
H6A	0.4756	0.1356	0.4840	0.044*
C7	0.38800 (10)	0.3379 (2)	0.48793 (8)	0.0451 (4)
H7A	0.3576	0.2982	0.5289	0.054*
C8	0.36356 (10)	0.4913 (2)	0.45416 (8)	0.0422 (4)
H8A	0.3159	0.5595	0.4710	0.051*
C9	0.40988 (10)	0.5434 (2)	0.39540 (8)	0.0404 (4)
H9A	0.3932	0.6500	0.3724	0.048*
C10	0.65082 (8)	0.32628 (16)	0.34860 (7)	0.0271 (3)
C11	0.64603 (9)	0.43720 (18)	0.28956 (7)	0.0332 (3)
H11A	0.5965	0.4342	0.2563	0.040*
C12	0.71530 (10)	0.5528 (2)	0.28022 (8)	0.0409 (4)
H12A	0.7141	0.6297	0.2399	0.049*
C13	0.78587 (9)	0.5555 (2)	0.32971 (8)	0.0408 (4)
H13A	0.8334	0.6355	0.3248	0.049*
C14	0.78572 (9)	0.43999 (19)	0.38630 (8)	0.0365 (3)
H14A	0.8346	0.4407	0.4202	0.044*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0356 (5)	0.0337 (6)	0.0367 (5)	0.0045 (4)	−0.0028 (4)	0.0119 (4)
N1	0.0257 (7)	0.0235 (8)	0.0284 (8)	0.000	0.0033 (6)	0.000
N2	0.0288 (5)	0.0350 (6)	0.0330 (6)	0.0044 (5)	0.0002 (5)	−0.0012 (5)
N3	0.0393 (6)	0.0329 (6)	0.0340 (6)	0.0083 (5)	0.0042 (5)	0.0034 (5)
C1	0.0531 (12)	0.0199 (10)	0.0501 (13)	0.000	0.0054 (10)	0.000
C2	0.0412 (7)	0.0266 (7)	0.0400 (8)	0.0029 (6)	0.0032 (6)	0.0064 (6)
C3	0.0255 (6)	0.0254 (7)	0.0317 (7)	0.0015 (5)	0.0072 (5)	0.0032 (5)
C4	0.0292 (6)	0.0259 (7)	0.0292 (7)	0.0026 (5)	0.0003 (5)	0.0059 (5)
C5	0.0271 (6)	0.0295 (7)	0.0267 (6)	−0.0008 (5)	−0.0019 (5)	−0.0014 (5)
C6	0.0354 (7)	0.0376 (8)	0.0359 (8)	0.0001 (6)	0.0031 (6)	0.0056 (6)
C7	0.0390 (8)	0.0616 (10)	0.0357 (8)	0.0001 (7)	0.0117 (6)	0.0001 (7)
C8	0.0363 (7)	0.0542 (10)	0.0361 (8)	0.0113 (7)	0.0031 (6)	−0.0089 (7)
C9	0.0480 (8)	0.0389 (8)	0.0342 (7)	0.0142 (7)	0.0011 (6)	−0.0019 (7)
C10	0.0260 (6)	0.0264 (6)	0.0291 (7)	0.0033 (5)	0.0036 (5)	−0.0027 (5)
C11	0.0322 (7)	0.0339 (7)	0.0332 (7)	−0.0040 (5)	−0.0009 (6)	0.0031 (6)
C12	0.0404 (8)	0.0437 (9)	0.0387 (8)	−0.0096 (6)	0.0020 (6)	0.0081 (7)
C13	0.0325 (7)	0.0455 (9)	0.0447 (8)	−0.0102 (6)	0.0053 (6)	−0.0015 (7)
C14	0.0263 (6)	0.0425 (8)	0.0405 (8)	−0.0002 (6)	−0.0015 (6)	−0.0054 (6)

Geometric parameters (Å, º)

O1—C4	1.4164 (15)	C5—C6	1.3871 (18)
O1—H1	0.89 (2)	C6—C7	1.383 (2)
N1—C3^i	1.3390 (15)	C6—H6A	0.950
N1—C3	1.3390 (15)	C7—C8	1.375 (2)
N2—C10	1.3340 (16)	C7—H7A	0.950
N2—C14	1.3423 (18)	C8—C9	1.373 (2)
N3—C5	1.3299 (17)	C8—H8A	0.950
N3—C9	1.3310 (18)	C9—H9A	0.950
C1—C2^i	1.3802 (18)	C10—C11	1.3830 (19)
C1—C2	1.3803 (18)	C11—C12	1.3852 (19)
C1—H1A	0.950	C11—H11A	0.950
C2—C3	1.3899 (19)	C12—C13	1.377 (2)
C2—H2A	0.950	C12—H12A	0.950
C3—C4	1.5380 (18)	C13—C14	1.371 (2)
C4—C10	1.5441 (17)	C13—H13A	0.950
C4—C5	1.5463 (17)	C14—H14A	0.950
C4—O1—H1	103.7 (14)	C8—C7—C6	119.15 (14)
C3^i—N1—C3	118.96 (15)	C8—C7—H7A	120.4
C10—N2—C14	118.24 (12)	C6—C7—H7A	120.4
C5—N3—C9	117.72 (12)	C9—C8—C7	118.16 (13)
C2^i—C1—C2	120.01 (18)	C9—C8—H8A	120.9
C2^i—C1—H1A	120.0	C7—C8—H8A	120.9
C2—C1—H1A	120.0	N3—C9—C8	123.85 (14)
C1—C2—C3	118.27 (14)	N3—C9—H9A	118.1
C1—C2—H2A	120.9	C8—C9—H9A	118.1
C3—C2—H2A	120.9	N2—C10—C11	122.43 (12)
N1—C3—C2	122.25 (13)	N2—C10—C4	113.09 (11)
N1—C3—C4	116.72 (11)	C11—C10—C4	124.38 (11)
C2—C3—C4	120.97 (12)	C10—C11—C12	118.31 (12)
O1—C4—C3	107.90 (10)	C10—C11—H11A	120.8
O1—C4—C10	108.58 (10)	C12—C11—H11A	120.8
C3—C4—C10	113.90 (10)	C13—C12—C11	119.64 (14)
O1—C4—C5	108.76 (10)	C13—C12—H12A	120.2
C3—C4—C5	108.36 (10)	C11—C12—H12A	120.2
C10—C4—C5	109.23 (10)	C14—C13—C12	118.25 (13)
N3—C5—C6	122.59 (12)	C14—C13—H13A	120.9
N3—C5—C4	117.13 (11)	C12—C13—H13A	120.9
C6—C5—C4	120.27 (11)	N2—C14—C13	123.11 (13)
C7—C6—C5	118.53 (14)	N2—C14—H14A	118.4
C7—C6—H6A	120.7	C13—C14—H14A	118.4
C5—C6—H6A	120.7
C2^i—C1—C2—C3	0.33 (8)	C4—C5—C6—C7	−178.58 (12)
C3^i—N1—C3—C2	0.36 (9)	C5—C6—C7—C8	−0.1 (2)
C3^i—N1—C3—C4	−176.83 (11)	C6—C7—C8—C9	−0.3 (2)
C1—C2—C3—N1	−0.71 (18)	C5—N3—C9—C8	−0.3 (2)
C1—C2—C3—C4	176.37 (9)	C7—C8—C9—N3	0.5 (2)
N1—C3—C4—O1	178.34 (9)	C14—N2—C10—C11	1.20 (19)
C2—C3—C4—O1	1.11 (16)	C14—N2—C10—C4	−175.43 (11)
N1—C3—C4—C10	−61.04 (13)	O1—C4—C10—N2	−15.72 (14)
C2—C3—C4—C10	121.73 (13)	C3—C4—C10—N2	−135.97 (11)
N1—C3—C4—C5	60.74 (12)	C5—C4—C10—N2	102.73 (12)
C2—C3—C4—C5	−116.49 (13)	O1—C4—C10—C11	167.72 (12)
C9—N3—C5—C6	−0.2 (2)	C3—C4—C10—C11	47.47 (17)
C9—N3—C5—C4	178.79 (12)	C5—C4—C10—C11	−73.83 (15)
O1—C4—C5—N3	160.75 (11)	N2—C10—C11—C12	−0.6 (2)
C3—C4—C5—N3	−82.19 (13)	C4—C10—C11—C12	175.63 (13)
C10—C4—C5—N3	42.41 (15)	C10—C11—C12—C13	−0.6 (2)
O1—C4—C5—C6	−20.23 (16)	C11—C12—C13—C14	1.3 (2)
C3—C4—C5—C6	96.83 (14)	C10—N2—C14—C13	−0.5 (2)
C10—C4—C5—C6	−138.57 (12)	C12—C13—C14—N2	−0.7 (2)
N3—C5—C6—C7	0.4 (2)

Symmetry code: (i) −x+1, y, −z+1/2.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N2	0.89 (2)	1.90 (2)	2.5455 (15)	127.9 (19)