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In the title molecular co-crystal, C
6H
6O
3·C
4H
4N
2, symmetry-related O—H
N hydrogen bonds with O
N distances of 2.790 (3) and 2.818 (2) Å link molecules of 1,2,3-trihydroxybenzene and pyrimidine to form 18-membered rings which, in turn, are constituents of infinite chains created by O—H
O hydrogen bonds between hydroxy groups in positions 1 and 2 of neighbouring 1,2,3-trihydroxybenzene molecules. The infinite chains are further stacked in stepped columns by offset π-π interactions, and are linked by C—H
π interactions, resulting in a herringbone pattern.
Supporting information
CCDC reference: 283944
Key indicators
- Single-crystal X-ray study
- T = 173 K
- Mean (C-C) = 0.003 Å
- R factor = 0.052
- wR factor = 0.163
- Data-to-parameter ratio = 15.4
checkCIF/PLATON results
No syntax errors found
Datablock: I
Alert level B
DIFMX01_ALERT_2_B The maximum difference density is > 0.1*ZMAX*1.00
_refine_diff_density_max given = 1.017
Test value = 0.800
PLAT097_ALERT_2_B Maximum (Positive) Residual Density ............ 1.02 e/A 3
Alert level C
ABSTM02_ALERT_3_C The ratio of expected to reported Tmax/Tmin(RR') is < 0.90
Tmin and Tmax reported: 0.745 0.979
Tmin(prime) and Tmax expected: 0.967 0.979
RR(prime) = 0.770
Please check that your absorption correction is appropriate.
DIFMX02_ALERT_1_C The minimum difference density is > 0.1*ZMAX*0.75
The relevant atom site should be identified.
PLAT061_ALERT_3_C Tmax/Tmin Range Test RR' too Large ............. 0.77
PLAT094_ALERT_2_C Ratio of Maximum / Minimum Residual Density .... 3.78
0 ALERT level A = In general: serious problem
2 ALERT level B = Potentially serious problem
4 ALERT level C = Check and explain
0 ALERT level G = General alerts; check
1 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
2 ALERT type 3 Indicator that the structure quality may be low
0 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2002); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: X-SEED (Atwood & Barbour, 2003; Barbour, 2001); software used to prepare material for publication: X-SEED.
1,2,3-trihydroxybenzene:pyrimidine
top
Crystal data top
C6H6O3·C4H4N2 | F(000) = 432 |
Mr = 206.20 | Dx = 1.432 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P2ybc | Cell parameters from 2112 reflections |
a = 6.5952 (9) Å | θ = 3.0–27.1° |
b = 13.7481 (19) Å | µ = 0.11 mm−1 |
c = 10.5778 (15) Å | T = 173 K |
β = 94.051 (3)° | Block, colourless |
V = 956.7 (2) Å3 | 0.30 × 0.25 × 0.20 mm |
Z = 4 | |
Data collection top
Bruker APEX CCD area-detector diffractometer | 2112 independent reflections |
Radiation source: fine-focus sealed tube | 1415 reflections with I > 2 σ (I) |
Graphite monochromator | Rint = 0.030 |
ω scans | θmax = 27.1°, θmin = 3.0° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1997) | h = −8→8 |
Tmin = 0.745, Tmax = 0.979 | k = −17→16 |
5916 measured reflections | l = −8→13 |
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)] = 0.052 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.163 | H-atom parameters constrained |
S = 1.03 | w = 1/[σ2(Fo2) + (0.0584P)2] where P = (Fo2 + 2Fc2)/3 |
2112 reflections | (Δ/σ)max < 0.001 |
137 parameters | Δρmax = 1.02 e Å−3 |
0 restraints | Δρmin = −0.27 e Å−3 |
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 | x | y | z | Uiso*/Ueq | |
O1 | 0.1911 (2) | 0.43273 (12) | 0.60380 (15) | 0.0392 (5) | |
H1 | 0.1915 | 0.4200 | 0.5262 | 0.047* | |
O2 | 0.1300 (2) | 0.46508 (12) | 0.85521 (14) | 0.0343 (4) | |
H2 | 0.2265 | 0.4838 | 0.8135 | 0.041* | |
N2 | 0.5207 (3) | 0.43685 (13) | 0.21608 (17) | 0.0296 (5) | |
N1 | 0.2772 (3) | 0.38391 (14) | 0.35728 (18) | 0.0330 (5) | |
O3 | −0.2156 (3) | 0.39222 (13) | 0.95192 (17) | 0.0435 (5) | |
H3 | −0.1404 | 0.4369 | 0.9825 | 0.052* | |
C2 | −0.0086 (3) | 0.41519 (15) | 0.7770 (2) | 0.0274 (5) | |
C1 | 0.0170 (3) | 0.39868 (15) | 0.6491 (2) | 0.0286 (5) | |
C9 | 0.2296 (3) | 0.34766 (16) | 0.1375 (2) | 0.0317 (5) | |
H9 | 0.1525 | 0.3181 | 0.0686 | 0.038* | |
C8 | 0.1681 (3) | 0.34391 (16) | 0.2592 (2) | 0.0334 (5) | |
H8 | 0.0443 | 0.3119 | 0.2740 | 0.040* | |
C3 | −0.1830 (3) | 0.38006 (16) | 0.8283 (2) | 0.0316 (5) | |
C10 | 0.4084 (3) | 0.39646 (16) | 0.1204 (2) | 0.0297 (5) | |
H10 | 0.4531 | 0.4015 | 0.0373 | 0.036* | |
C7 | 0.4477 (4) | 0.42815 (16) | 0.3298 (2) | 0.0322 (5) | |
H7 | 0.5262 | 0.4567 | 0.3988 | 0.039* | |
C6 | −0.1310 (3) | 0.34815 (16) | 0.5741 (2) | 0.0355 (6) | |
H6 | −0.1132 | 0.3369 | 0.4870 | 0.043* | |
C5 | −0.3014 (4) | 0.31500 (18) | 0.6268 (3) | 0.0407 (6) | |
H5 | −0.4028 | 0.2816 | 0.5754 | 0.049* | |
C4 | −0.3279 (4) | 0.32936 (17) | 0.7536 (3) | 0.0406 (6) | |
H4 | −0.4453 | 0.3045 | 0.7895 | 0.049* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O1 | 0.0340 (9) | 0.0600 (11) | 0.0244 (9) | −0.0174 (8) | 0.0090 (7) | −0.0070 (8) |
O2 | 0.0270 (8) | 0.0527 (10) | 0.0239 (8) | −0.0082 (7) | 0.0076 (6) | −0.0015 (7) |
N2 | 0.0279 (9) | 0.0326 (10) | 0.0291 (11) | −0.0031 (7) | 0.0073 (8) | −0.0033 (8) |
N1 | 0.0316 (10) | 0.0379 (11) | 0.0304 (11) | −0.0063 (8) | 0.0075 (8) | −0.0015 (8) |
O3 | 0.0428 (10) | 0.0523 (11) | 0.0368 (10) | −0.0084 (8) | 0.0127 (8) | −0.0031 (8) |
C2 | 0.0244 (11) | 0.0265 (10) | 0.0317 (12) | 0.0001 (8) | 0.0035 (9) | 0.0024 (9) |
C1 | 0.0242 (11) | 0.0295 (11) | 0.0322 (12) | 0.0006 (9) | 0.0041 (9) | 0.0021 (9) |
C9 | 0.0313 (12) | 0.0355 (12) | 0.0283 (12) | −0.0019 (9) | 0.0026 (10) | −0.0028 (9) |
C8 | 0.0280 (11) | 0.0336 (12) | 0.0392 (14) | −0.0073 (9) | 0.0068 (10) | −0.0023 (10) |
C3 | 0.0318 (12) | 0.0293 (11) | 0.0349 (13) | 0.0037 (9) | 0.0121 (10) | 0.0026 (9) |
C10 | 0.0296 (12) | 0.0323 (11) | 0.0280 (12) | 0.0023 (9) | 0.0071 (9) | −0.0007 (9) |
C7 | 0.0318 (12) | 0.0374 (12) | 0.0276 (12) | −0.0056 (9) | 0.0036 (10) | −0.0047 (10) |
C6 | 0.0313 (12) | 0.0354 (12) | 0.0395 (13) | −0.0013 (10) | 0.0012 (10) | −0.0050 (10) |
C5 | 0.0327 (13) | 0.0387 (13) | 0.0508 (16) | −0.0084 (10) | 0.0041 (11) | −0.0110 (11) |
C4 | 0.0289 (12) | 0.0347 (12) | 0.0599 (17) | −0.0093 (10) | 0.0149 (12) | 0.0008 (12) |
Geometric parameters (Å, º) top
O1—C1 | 1.358 (3) | C9—C10 | 1.380 (3) |
O1—H1 | 0.8400 | C9—C8 | 1.378 (3) |
O2—C2 | 1.373 (3) | C9—H9 | 0.9500 |
O2—H2 | 0.8400 | C8—H8 | 0.9500 |
N2—C7 | 1.332 (3) | C3—C4 | 1.385 (3) |
N2—C10 | 1.332 (3) | C10—H10 | 0.9500 |
N1—C7 | 1.329 (3) | C7—H7 | 0.9500 |
N1—C8 | 1.338 (3) | C6—C5 | 1.368 (3) |
O3—C3 | 1.351 (3) | C6—H6 | 0.9500 |
O3—H3 | 0.8400 | C5—C4 | 1.378 (4) |
C2—C1 | 1.394 (3) | C5—H5 | 0.9500 |
C2—C3 | 1.393 (3) | C4—H4 | 0.9500 |
C1—C6 | 1.398 (3) | | |
| | | |
C1—O1—H1 | 109.5 | O3—C3—C2 | 121.8 (2) |
C2—O2—H2 | 109.5 | C4—C3—C2 | 120.5 (2) |
C7—N2—C10 | 115.54 (18) | N2—C10—C9 | 122.6 (2) |
C7—N1—C8 | 115.8 (2) | N2—C10—H10 | 118.7 |
C3—O3—H3 | 109.5 | C9—C10—H10 | 118.7 |
O2—C2—C1 | 123.05 (18) | N1—C7—N2 | 127.2 (2) |
O2—C2—C3 | 118.13 (19) | N1—C7—H7 | 116.4 |
C1—C2—C3 | 118.8 (2) | N2—C7—H7 | 116.4 |
O1—C1—C2 | 116.71 (19) | C5—C6—C1 | 119.7 (2) |
O1—C1—C6 | 123.0 (2) | C5—C6—H6 | 120.2 |
C2—C1—C6 | 120.2 (2) | C1—C6—H6 | 120.2 |
C10—C9—C8 | 116.8 (2) | C6—C5—C4 | 120.9 (2) |
C10—C9—H9 | 121.6 | C6—C5—H5 | 119.6 |
C8—C9—H9 | 121.6 | C4—C5—H5 | 119.6 |
N1—C8—C9 | 122.1 (2) | C5—C4—C3 | 119.8 (2) |
N1—C8—H8 | 118.9 | C5—C4—H4 | 120.1 |
C9—C8—H8 | 118.9 | C3—C4—H4 | 120.1 |
O3—C3—C4 | 117.7 (2) | | |
| | | |
O2—C2—C1—O1 | 1.5 (3) | C7—N2—C10—C9 | −0.8 (3) |
C3—C2—C1—O1 | −178.84 (19) | C8—C9—C10—N2 | 1.3 (3) |
O2—C2—C1—C6 | −179.3 (2) | C8—N1—C7—N2 | 0.1 (4) |
C3—C2—C1—C6 | 0.3 (3) | C10—N2—C7—N1 | 0.1 (3) |
C7—N1—C8—C9 | 0.5 (3) | O1—C1—C6—C5 | 179.2 (2) |
C10—C9—C8—N1 | −1.2 (3) | C2—C1—C6—C5 | 0.1 (3) |
O2—C2—C3—O3 | −1.4 (3) | C1—C6—C5—C4 | −1.1 (4) |
C1—C2—C3—O3 | 178.9 (2) | C6—C5—C4—C3 | 1.6 (4) |
O2—C2—C3—C4 | 179.9 (2) | O3—C3—C4—C5 | −180.0 (2) |
C1—C2—C3—C4 | 0.2 (3) | C2—C3—C4—C5 | −1.2 (4) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1···N1 | 0.84 | 1.98 | 2.790 (3) | 163 |
O2—H2···N2i | 0.84 | 2.04 | 2.818 (2) | 155 |
O3—H3···O2ii | 0.84 | 2.18 | 2.858 (2) | 138 |
Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) −x, −y+1, −z+2. |
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