In the crystal structure of the title complex, C
10H
8N
2·C
6H
4O
4S or bpy·tdc (bpy is 4,4′-bipyridine and tdc is thiophene-2,5-dicarboxylic acid), bpy and tdc form one-dimensional zigzag chains as a result of O—H
N hydrogen bonds. These chains are further assembled into layers by van der Waals attractions, which are extended into a three-dimensional network by van der Waals and aromatic π–π stacking interactions.
Supporting information
CCDC reference: 255929
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.003 Å
- R factor = 0.055
- wR factor = 0.145
- Data-to-parameter ratio = 15.6
checkCIF/PLATON results
No syntax errors found
Alert level B
DENSM01_ALERT_1_B _exptl_crystal_density_method is given but no
value of _exptl_crystal_density_meas is reported.
Alert level C
PLAT094_ALERT_2_C Ratio of Maximum / Minimum Residual Density .... 2.23
PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor .... 2.10
PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd. # 1
C10 H8 N2
0 ALERT level A = In general: serious problem
1 ALERT level B = Potentially serious problem
3 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
2 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
Data collection: R3m Software (Siemens, 1990); cell refinement: R3m Software; data reduction: R3m Software; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Sheldrick, 1998); software used to prepare material for publication: SHELXL97.
Crystal data top
C10H8N2·C6H4O4S | F(000) = 680 |
Mr = 328.34 | Dx = 1.462 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 25 reflections |
a = 6.8598 (6) Å | θ = 2–27° |
b = 10.3438 (9) Å | µ = 0.24 mm−1 |
c = 21.1315 (18) Å | T = 293 K |
β = 95.718 (2)° | Block, colorless |
V = 1492.0 (2) Å3 | 0.52 × 0.46 × 0.18 mm |
Z = 4 | |
Data collection top
Siemens R3m diffractometer | 2620 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.021 |
Graphite monochromator | θmax = 27.0°, θmin = 1.9° |
ω scans | h = −8→7 |
Absorption correction: ψ scan (North et al., 1968) | k = −10→13 |
Tmin = 0.886, Tmax = 0.958 | l = −26→26 |
8861 measured reflections | 2 standard reflections every 200 reflections |
3243 independent reflections | intensity decay: none |
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)] = 0.055 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.145 | H-atom parameters constrained |
S = 1.07 | w = 1/[σ2(Fo2) + (0.0724P)2 + 0.482P] where P = (Fo2 + 2Fc2)/3 |
3243 reflections | (Δ/σ)max < 0.001 |
208 parameters | Δρmax = 0.46 e Å−3 |
0 restraints | Δρmin = −0.21 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 | |
S1 | 0.33851 (9) | 0.33146 (5) | 0.36381 (3) | 0.0512 (2) | |
O1 | 0.0293 (3) | 0.27661 (18) | 0.44562 (8) | 0.0639 (5) | |
H1A | −0.0589 | 0.2579 | 0.4675 | 0.096* | |
O2 | −0.1340 (3) | 0.4639 (2) | 0.43246 (9) | 0.0711 (5) | |
O3 | 0.6885 (3) | 0.31486 (16) | 0.28917 (10) | 0.0689 (5) | |
O4 | 0.6846 (2) | 0.52304 (15) | 0.26145 (8) | 0.0560 (4) | |
H4B | 0.7831 | 0.5031 | 0.2446 | 0.084* | |
N1 | 0.0053 (3) | 0.97041 (18) | 0.29659 (8) | 0.0449 (4) | |
N2 | −0.7472 (3) | 0.7996 (2) | 0.48496 (9) | 0.0604 (6) | |
C1 | −0.2355 (3) | 1.0308 (2) | 0.36496 (10) | 0.0470 (5) | |
H1B | −0.2952 | 1.0963 | 0.3862 | 0.056* | |
C2 | −0.0833 (3) | 1.0590 (2) | 0.32885 (11) | 0.0473 (5) | |
H2B | −0.0412 | 1.1443 | 0.3271 | 0.057* | |
C3 | −0.0590 (3) | 0.8489 (2) | 0.29852 (11) | 0.0498 (6) | |
H3A | −0.0011 | 0.7864 | 0.2749 | 0.060* | |
C4 | −0.2075 (3) | 0.8121 (2) | 0.33394 (11) | 0.0492 (5) | |
H4A | −0.2472 | 0.7261 | 0.3344 | 0.059* | |
C5 | −0.2977 (3) | 0.9042 (2) | 0.36905 (9) | 0.0406 (5) | |
C6 | −0.4538 (3) | 0.8681 (2) | 0.40956 (10) | 0.0432 (5) | |
C7 | −0.4479 (4) | 0.7505 (2) | 0.44161 (11) | 0.0539 (6) | |
H7A | −0.3452 | 0.6929 | 0.4384 | 0.065* | |
C8 | −0.5986 (4) | 0.7209 (3) | 0.47847 (12) | 0.0601 (7) | |
H8A | −0.5949 | 0.6419 | 0.4996 | 0.072* | |
C9 | −0.7522 (4) | 0.9121 (3) | 0.45458 (12) | 0.0625 (7) | |
H9A | −0.8563 | 0.9679 | 0.4590 | 0.075* | |
C10 | −0.6097 (3) | 0.9497 (3) | 0.41673 (11) | 0.0546 (6) | |
H10A | −0.6183 | 1.0294 | 0.3962 | 0.066* | |
C11 | 0.0010 (3) | 0.3943 (2) | 0.42296 (11) | 0.0515 (6) | |
C12 | 0.1569 (3) | 0.4341 (2) | 0.38291 (10) | 0.0453 (5) | |
C13 | 0.1743 (3) | 0.5525 (2) | 0.35691 (11) | 0.0518 (6) | |
H13A | 0.0885 | 0.6204 | 0.3622 | 0.062* | |
C14 | 0.3363 (3) | 0.5623 (2) | 0.32102 (11) | 0.0479 (5) | |
H14A | 0.3690 | 0.6370 | 0.3000 | 0.057* | |
C15 | 0.4386 (3) | 0.45029 (19) | 0.32068 (10) | 0.0408 (5) | |
C16 | 0.6172 (3) | 0.4214 (2) | 0.28896 (11) | 0.0439 (5) | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
S1 | 0.0509 (4) | 0.0441 (3) | 0.0622 (4) | 0.0009 (2) | 0.0242 (3) | 0.0085 (3) |
O1 | 0.0582 (11) | 0.0716 (12) | 0.0669 (11) | −0.0071 (9) | 0.0309 (9) | 0.0095 (9) |
O2 | 0.0535 (11) | 0.0878 (13) | 0.0771 (12) | 0.0097 (10) | 0.0319 (9) | 0.0044 (10) |
O3 | 0.0690 (12) | 0.0449 (10) | 0.1000 (14) | 0.0071 (8) | 0.0441 (11) | 0.0040 (9) |
O4 | 0.0540 (10) | 0.0448 (9) | 0.0755 (11) | 0.0014 (7) | 0.0367 (8) | 0.0036 (8) |
N1 | 0.0409 (10) | 0.0494 (10) | 0.0469 (10) | 0.0040 (8) | 0.0174 (8) | 0.0044 (8) |
N2 | 0.0514 (12) | 0.0823 (15) | 0.0503 (11) | −0.0084 (11) | 0.0198 (9) | 0.0043 (10) |
C1 | 0.0483 (12) | 0.0440 (12) | 0.0517 (12) | 0.0023 (10) | 0.0210 (10) | −0.0028 (9) |
C2 | 0.0484 (13) | 0.0414 (11) | 0.0551 (13) | 0.0003 (9) | 0.0205 (10) | 0.0024 (10) |
C3 | 0.0492 (13) | 0.0492 (13) | 0.0544 (13) | 0.0067 (10) | 0.0220 (11) | −0.0032 (10) |
C4 | 0.0495 (13) | 0.0424 (11) | 0.0586 (13) | −0.0010 (9) | 0.0190 (11) | −0.0012 (10) |
C5 | 0.0351 (10) | 0.0482 (12) | 0.0399 (10) | 0.0015 (8) | 0.0117 (8) | 0.0020 (9) |
C6 | 0.0391 (11) | 0.0518 (12) | 0.0405 (10) | −0.0038 (9) | 0.0125 (9) | 0.0001 (9) |
C7 | 0.0510 (13) | 0.0578 (14) | 0.0548 (13) | −0.0005 (11) | 0.0153 (11) | 0.0062 (11) |
C8 | 0.0645 (16) | 0.0651 (16) | 0.0525 (13) | −0.0106 (13) | 0.0142 (12) | 0.0112 (12) |
C9 | 0.0467 (14) | 0.0838 (19) | 0.0607 (15) | 0.0071 (12) | 0.0236 (12) | 0.0085 (13) |
C10 | 0.0471 (13) | 0.0641 (15) | 0.0555 (13) | 0.0058 (11) | 0.0195 (11) | 0.0097 (11) |
C11 | 0.0464 (13) | 0.0640 (15) | 0.0459 (12) | −0.0040 (11) | 0.0136 (10) | −0.0004 (11) |
C12 | 0.0385 (11) | 0.0556 (13) | 0.0434 (11) | −0.0004 (9) | 0.0120 (9) | −0.0024 (9) |
C13 | 0.0438 (12) | 0.0532 (13) | 0.0608 (14) | 0.0070 (10) | 0.0172 (11) | 0.0008 (11) |
C14 | 0.0443 (12) | 0.0436 (12) | 0.0577 (13) | −0.0001 (9) | 0.0148 (10) | 0.0044 (10) |
C15 | 0.0402 (11) | 0.0392 (10) | 0.0446 (11) | −0.0046 (8) | 0.0131 (9) | 0.0002 (8) |
C16 | 0.0409 (11) | 0.0410 (11) | 0.0522 (12) | −0.0022 (9) | 0.0160 (9) | −0.0026 (9) |
Geometric parameters (Å, º) top
S1—C15 | 1.714 (2) | C4—C5 | 1.390 (3) |
S1—C12 | 1.716 (2) | C4—H4A | 0.9300 |
O1—C11 | 1.316 (3) | C5—C6 | 1.484 (3) |
O1—H1A | 0.8200 | C6—C10 | 1.383 (3) |
O2—C11 | 1.206 (3) | C6—C7 | 1.391 (3) |
O3—C16 | 1.205 (3) | C7—C8 | 1.390 (3) |
O4—C16 | 1.308 (2) | C7—H7A | 0.9300 |
O4—H4B | 0.8200 | C8—H8A | 0.9300 |
N1—C2 | 1.326 (3) | C9—C10 | 1.380 (3) |
N1—C3 | 1.334 (3) | C9—H9A | 0.9300 |
N2—C8 | 1.322 (3) | C10—H10A | 0.9300 |
N2—C9 | 1.327 (3) | C11—C12 | 1.486 (3) |
C1—C5 | 1.383 (3) | C12—C13 | 1.352 (3) |
C1—C2 | 1.384 (3) | C13—C14 | 1.410 (3) |
C1—H1B | 0.9300 | C13—H13A | 0.9300 |
C2—H2B | 0.9300 | C14—C15 | 1.355 (3) |
C3—C4 | 1.376 (3) | C14—H14A | 0.9300 |
C3—H3A | 0.9300 | C15—C16 | 1.484 (3) |
| | | |
C15—S1—C12 | 91.15 (10) | N2—C8—H8A | 118.4 |
C11—O1—H1A | 109.5 | C7—C8—H8A | 118.4 |
C16—O4—H4B | 109.5 | N2—C9—C10 | 122.8 (2) |
C2—N1—C3 | 117.75 (18) | N2—C9—H9A | 118.6 |
C8—N2—C9 | 118.2 (2) | C10—C9—H9A | 118.6 |
C5—C1—C2 | 119.25 (19) | C9—C10—C6 | 119.5 (2) |
C5—C1—H1B | 120.4 | C9—C10—H10A | 120.3 |
C2—C1—H1B | 120.4 | C6—C10—H10A | 120.3 |
N1—C2—C1 | 123.2 (2) | O2—C11—O1 | 125.4 (2) |
N1—C2—H2B | 118.4 | O2—C11—C12 | 122.5 (2) |
C1—C2—H2B | 118.4 | O1—C11—C12 | 112.1 (2) |
N1—C3—C4 | 122.8 (2) | C13—C12—C11 | 125.5 (2) |
N1—C3—H3A | 118.6 | C13—C12—S1 | 111.66 (16) |
C4—C3—H3A | 118.6 | C11—C12—S1 | 122.88 (18) |
C3—C4—C5 | 119.6 (2) | C12—C13—C14 | 112.9 (2) |
C3—C4—H4A | 120.2 | C12—C13—H13A | 123.5 |
C5—C4—H4A | 120.2 | C14—C13—H13A | 123.5 |
C1—C5—C4 | 117.33 (19) | C15—C14—C13 | 112.2 (2) |
C1—C5—C6 | 121.27 (19) | C15—C14—H14A | 123.9 |
C4—C5—C6 | 121.4 (2) | C13—C14—H14A | 123.9 |
C10—C6—C7 | 117.8 (2) | C14—C15—C16 | 128.77 (19) |
C10—C6—C5 | 121.3 (2) | C14—C15—S1 | 112.01 (15) |
C7—C6—C5 | 120.9 (2) | C16—C15—S1 | 119.22 (16) |
C8—C7—C6 | 118.6 (2) | O3—C16—O4 | 125.1 (2) |
C8—C7—H7A | 120.7 | O3—C16—C15 | 122.38 (19) |
C6—C7—H7A | 120.7 | O4—C16—C15 | 112.52 (18) |
N2—C8—C7 | 123.1 (2) | | |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1A···N2i | 0.82 | 1.84 | 2.662 (2) | 175 |
O4—H4B···N1ii | 0.82 | 1.80 | 2.616 (2) | 175 |
Symmetry codes: (i) −x−1, −y+1, −z+1; (ii) −x+1, y−1/2, −z+1/2. |