Buy article online - an online subscription or single-article purchase is required to access this article.
In the crystal structure of
meso-1,2-bis(pyridin-2-yl)ethane-1,2-diol, C
12H
12N
2O
2, at 180 K, the molecules lie on inversion centres and are linked into ribbons by complementary O—H
N hydrogen bonds.
Supporting information
CCDC reference: 269789
Key indicators
- Single-crystal X-ray study
- T = 180 K
- Mean (C-C) = 0.004 Å
- R factor = 0.059
- wR factor = 0.147
- Data-to-parameter ratio = 16.5
checkCIF/PLATON results
No syntax errors found
Alert level B
ABSTM02_ALERT_3_B The ratio of expected to reported Tmax/Tmin(RR') is < 0.75
Tmin and Tmax reported: 0.588 0.992
Tmin' and Tmax expected: 0.971 0.992
RR' = 0.606
Please check that your absorption correction is appropriate.
PLAT061_ALERT_3_B Tmax/Tmin Range Test RR' too Large ............. 0.61
0 ALERT level A = In general: serious problem
2 ALERT level B = Potentially serious problem
0 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
Data collection: APEX2 v.1.0-22 (Bruker-Nonius, 2004); cell refinement: SAINT v.7.06a (Bruker, 2003); data reduction: SAINT v.7.06a (Bruker, 2003); program(s) used to solve structure: SHELXTL v.6.10 (Sheldrick, 2000); program(s) used to refine structure: SHELXTL v.6.10 (Sheldrick, 2000); molecular graphics: SHELXTL v.6.10 (Sheldrick, 2000); software used to prepare material for publication: SHELXTL v.6.10 (Sheldrick, 2000).
meso-1,2-bis(pyridin-2-yl)-ethane-1,2-diol
top
Crystal data top
C12H12N2O2 | F(000) = 228 |
Mr = 216.24 | Dx = 1.420 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 1853 reflections |
a = 5.3155 (14) Å | θ = 3.8–25.1° |
b = 8.108 (2) Å | µ = 0.10 mm−1 |
c = 11.737 (3) Å | T = 180 K |
β = 90.196 (10)° | Needle, pale orange |
V = 505.8 (2) Å3 | 0.30 × 0.08 × 0.08 mm |
Z = 2 | |
Data collection top
Bruker-Nonius X8APEX-II CCD diffractometer | 1236 independent reflections |
Radiation source: fine-focus sealed tube | 1026 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.043 |
thin–slice ω and φ scans | θmax = 28.3°, θmin = 3.8° |
Absorption correction: multi-scan SADABS v.2.10 (Sheldrick, 2003)
Ratio of minimum to maximum apparent transmission: 0.592890 | h = −7→6 |
Tmin = 0.588, Tmax = 0.992 | k = −10→8 |
6075 measured reflections | l = −15→12 |
Refinement top
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.059 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.147 | H-atom parameters constrained |
S = 1.11 | w = 1/[σ2(Fo2) + (0.0396P)2 + 0.2558P] where P = (Fo2 + 2Fc2)/3 |
1236 reflections | (Δ/σ)max < 0.001 |
75 parameters | Δρmax = 0.32 e Å−3 |
0 restraints | Δρmin = −0.25 e Å−3 |
Special details top
Experimental. Crystal is monoclinic with beta close to 90 °. and is twinned to appear
orthorhombic: Twin law (1 0 0, 0 - 1 0, 0 0 - 1), BASF: 0.386 (3). H atom of OH group added in calculated position and allowed to rotate about the
C—O bond to the position of maximum electron density (AFIX 147). |
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 | x | y | z | Uiso*/Ueq | |
O1 | 0.2162 (3) | 0.1732 (2) | 0.49298 (15) | 0.0331 (5) | |
H1 | 0.3366 | 0.1713 | 0.4468 | 0.050* | |
N1 | 0.3968 (4) | −0.1194 (3) | 0.66357 (17) | 0.0318 (5) | |
C1 | 0.1884 (5) | −0.0311 (3) | 0.6412 (2) | 0.0279 (5) | |
C2 | 0.0389 (6) | 0.0309 (3) | 0.7274 (2) | 0.0334 (6) | |
H2A | −0.1091 | 0.0916 | 0.7098 | 0.040* | |
C3 | 0.1081 (6) | 0.0033 (3) | 0.8400 (2) | 0.0363 (6) | |
H3A | 0.0090 | 0.0458 | 0.9005 | 0.044* | |
C4 | 0.3233 (6) | −0.0870 (3) | 0.8629 (2) | 0.0355 (6) | |
H4A | 0.3747 | −0.1079 | 0.9392 | 0.043* | |
C5 | 0.4599 (5) | −0.1453 (3) | 0.7733 (2) | 0.0354 (6) | |
H5A | 0.6074 | −0.2075 | 0.7892 | 0.042* | |
C6 | 0.1359 (5) | 0.0076 (3) | 0.5162 (2) | 0.0302 (6) | |
H6A | 0.2362 | −0.0697 | 0.4680 | 0.036* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O1 | 0.0437 (10) | 0.0305 (9) | 0.0250 (9) | −0.0066 (8) | 0.0041 (8) | 0.0037 (8) |
N1 | 0.0324 (11) | 0.0366 (11) | 0.0265 (9) | 0.0023 (9) | 0.0010 (9) | 0.0053 (9) |
C1 | 0.0351 (13) | 0.0292 (12) | 0.0195 (10) | 0.0012 (10) | −0.0004 (10) | 0.0028 (9) |
C2 | 0.0400 (15) | 0.0358 (14) | 0.0245 (12) | 0.0068 (11) | 0.0029 (11) | 0.0008 (10) |
C3 | 0.0533 (16) | 0.0316 (12) | 0.0240 (11) | −0.0030 (12) | 0.0027 (12) | −0.0024 (11) |
C4 | 0.0537 (17) | 0.0356 (14) | 0.0170 (10) | −0.0097 (13) | −0.0083 (11) | 0.0075 (10) |
C5 | 0.0341 (14) | 0.0360 (13) | 0.0361 (15) | −0.0012 (11) | −0.0036 (11) | 0.0092 (11) |
C6 | 0.0404 (14) | 0.0322 (12) | 0.0179 (10) | 0.0034 (10) | 0.0042 (10) | 0.0013 (9) |
Geometric parameters (Å, º) top
O1—C6 | 1.435 (3) | C3—C4 | 1.384 (4) |
O1—H1 | 0.840 | C3—H3A | 0.950 |
N1—C1 | 1.344 (3) | C4—C5 | 1.365 (4) |
N1—C5 | 1.347 (3) | C4—H4A | 0.950 |
C1—C2 | 1.383 (3) | C5—H5A | 0.950 |
C1—C6 | 1.525 (3) | C6—C6i | 1.498 (5) |
C2—C3 | 1.389 (4) | C6—H6A | 1.000 |
C2—H2A | 0.950 | | |
| | | |
C6—O1—H1 | 109.5 | C5—C4—H4A | 120.8 |
C1—N1—C5 | 118.2 (2) | C3—C4—H4A | 120.8 |
N1—C1—C2 | 121.8 (2) | N1—C5—C4 | 123.5 (3) |
N1—C1—C6 | 116.4 (2) | N1—C5—H5A | 118.3 |
C2—C1—C6 | 121.7 (2) | C4—C5—H5A | 118.3 |
C1—C2—C3 | 119.1 (3) | O1—C6—C6i | 108.4 (3) |
C1—C2—H2A | 120.5 | O1—C6—C1 | 108.79 (19) |
C3—C2—H2A | 120.5 | C6i—C6—C1 | 113.6 (3) |
C4—C3—C2 | 119.1 (3) | O1—C6—H6A | 108.6 |
C4—C3—H3A | 120.4 | C6i—C6—H6A | 108.6 |
C2—C3—H3A | 120.4 | C1—C6—H6A | 108.6 |
C5—C4—C3 | 118.4 (2) | | |
| | | |
C5—N1—C1—C2 | −0.7 (4) | C1—N1—C5—C4 | 0.1 (4) |
C5—N1—C1—C6 | 175.0 (2) | C3—C4—C5—N1 | 0.1 (4) |
N1—C1—C2—C3 | 1.0 (4) | N1—C1—C6—O1 | −99.9 (2) |
C6—C1—C2—C3 | −174.5 (2) | C2—C1—C6—O1 | 75.8 (3) |
C1—C2—C3—C4 | −0.7 (4) | N1—C1—C6—C6i | 139.2 (3) |
C2—C3—C4—C5 | 0.1 (4) | C2—C1—C6—C6i | −45.1 (4) |
Symmetry code: (i) −x, −y, −z+1. |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1···N1ii | 0.84 | 1.97 | 2.797 (3) | 169 |
Symmetry code: (ii) −x+1, −y, −z+1. |
Subscribe to Acta Crystallographica Section E: Crystallographic Communications
The full text of this article is available to subscribers to the journal.
If you have already registered and are using a computer listed in your registration details, please email
support@iucr.org for assistance.