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In the crystal structure of the title complex, C10H8N2·C6H4O4S 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

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S160053680402639X/bv6003sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S160053680402639X/bv6003Isup2.hkl
Contains datablock I

CCDC reference: 255929

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](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

Computing details top

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.

(I) top
Crystal data top
C10H8N2·C6H4O4SF(000) = 680
Mr = 328.34Dx = 1.462 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 25 reflections
a = 6.8598 (6) Åθ = 2–27°
b = 10.3438 (9) ŵ = 0.24 mm1
c = 21.1315 (18) ÅT = 293 K
β = 95.718 (2)°Block, colorless
V = 1492.0 (2) Å30.52 × 0.46 × 0.18 mm
Z = 4
Data collection top
Siemens R3m
diffractometer
2620 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.021
Graphite monochromatorθmax = 27.0°, θmin = 1.9°
ω scansh = 87
Absorption correction: ψ scan
(North et al., 1968)
k = 1013
Tmin = 0.886, Tmax = 0.958l = 2626
8861 measured reflections2 standard reflections every 200 reflections
3243 independent reflections intensity decay: none
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.055Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.145H-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 parametersΔρmax = 0.46 e Å3
0 restraintsΔρmin = 0.21 e Å3
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 &gt; 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
xyzUiso*/Ueq
S10.33851 (9)0.33146 (5)0.36381 (3)0.0512 (2)
O10.0293 (3)0.27661 (18)0.44562 (8)0.0639 (5)
H1A0.05890.25790.46750.096*
O20.1340 (3)0.4639 (2)0.43246 (9)0.0711 (5)
O30.6885 (3)0.31486 (16)0.28917 (10)0.0689 (5)
O40.6846 (2)0.52304 (15)0.26145 (8)0.0560 (4)
H4B0.78310.50310.24460.084*
N10.0053 (3)0.97041 (18)0.29659 (8)0.0449 (4)
N20.7472 (3)0.7996 (2)0.48496 (9)0.0604 (6)
C10.2355 (3)1.0308 (2)0.36496 (10)0.0470 (5)
H1B0.29521.09630.38620.056*
C20.0833 (3)1.0590 (2)0.32885 (11)0.0473 (5)
H2B0.04121.14430.32710.057*
C30.0590 (3)0.8489 (2)0.29852 (11)0.0498 (6)
H3A0.00110.78640.27490.060*
C40.2075 (3)0.8121 (2)0.33394 (11)0.0492 (5)
H4A0.24720.72610.33440.059*
C50.2977 (3)0.9042 (2)0.36905 (9)0.0406 (5)
C60.4538 (3)0.8681 (2)0.40956 (10)0.0432 (5)
C70.4479 (4)0.7505 (2)0.44161 (11)0.0539 (6)
H7A0.34520.69290.43840.065*
C80.5986 (4)0.7209 (3)0.47847 (12)0.0601 (7)
H8A0.59490.64190.49960.072*
C90.7522 (4)0.9121 (3)0.45458 (12)0.0625 (7)
H9A0.85630.96790.45900.075*
C100.6097 (3)0.9497 (3)0.41673 (11)0.0546 (6)
H10A0.61831.02940.39620.066*
C110.0010 (3)0.3943 (2)0.42296 (11)0.0515 (6)
C120.1569 (3)0.4341 (2)0.38291 (10)0.0453 (5)
C130.1743 (3)0.5525 (2)0.35691 (11)0.0518 (6)
H13A0.08850.62040.36220.062*
C140.3363 (3)0.5623 (2)0.32102 (11)0.0479 (5)
H14A0.36900.63700.30000.057*
C150.4386 (3)0.45029 (19)0.32068 (10)0.0408 (5)
C160.6172 (3)0.4214 (2)0.28896 (11)0.0439 (5)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.0509 (4)0.0441 (3)0.0622 (4)0.0009 (2)0.0242 (3)0.0085 (3)
O10.0582 (11)0.0716 (12)0.0669 (11)0.0071 (9)0.0309 (9)0.0095 (9)
O20.0535 (11)0.0878 (13)0.0771 (12)0.0097 (10)0.0319 (9)0.0044 (10)
O30.0690 (12)0.0449 (10)0.1000 (14)0.0071 (8)0.0441 (11)0.0040 (9)
O40.0540 (10)0.0448 (9)0.0755 (11)0.0014 (7)0.0367 (8)0.0036 (8)
N10.0409 (10)0.0494 (10)0.0469 (10)0.0040 (8)0.0174 (8)0.0044 (8)
N20.0514 (12)0.0823 (15)0.0503 (11)0.0084 (11)0.0198 (9)0.0043 (10)
C10.0483 (12)0.0440 (12)0.0517 (12)0.0023 (10)0.0210 (10)0.0028 (9)
C20.0484 (13)0.0414 (11)0.0551 (13)0.0003 (9)0.0205 (10)0.0024 (10)
C30.0492 (13)0.0492 (13)0.0544 (13)0.0067 (10)0.0220 (11)0.0032 (10)
C40.0495 (13)0.0424 (11)0.0586 (13)0.0010 (9)0.0190 (11)0.0012 (10)
C50.0351 (10)0.0482 (12)0.0399 (10)0.0015 (8)0.0117 (8)0.0020 (9)
C60.0391 (11)0.0518 (12)0.0405 (10)0.0038 (9)0.0125 (9)0.0001 (9)
C70.0510 (13)0.0578 (14)0.0548 (13)0.0005 (11)0.0153 (11)0.0062 (11)
C80.0645 (16)0.0651 (16)0.0525 (13)0.0106 (13)0.0142 (12)0.0112 (12)
C90.0467 (14)0.0838 (19)0.0607 (15)0.0071 (12)0.0236 (12)0.0085 (13)
C100.0471 (13)0.0641 (15)0.0555 (13)0.0058 (11)0.0195 (11)0.0097 (11)
C110.0464 (13)0.0640 (15)0.0459 (12)0.0040 (11)0.0136 (10)0.0004 (11)
C120.0385 (11)0.0556 (13)0.0434 (11)0.0004 (9)0.0120 (9)0.0024 (9)
C130.0438 (12)0.0532 (13)0.0608 (14)0.0070 (10)0.0172 (11)0.0008 (11)
C140.0443 (12)0.0436 (12)0.0577 (13)0.0001 (9)0.0148 (10)0.0044 (10)
C150.0402 (11)0.0392 (10)0.0446 (11)0.0046 (8)0.0131 (9)0.0002 (8)
C160.0409 (11)0.0410 (11)0.0522 (12)0.0022 (9)0.0160 (9)0.0026 (9)
Geometric parameters (Å, º) top
S1—C151.714 (2)C4—C51.390 (3)
S1—C121.716 (2)C4—H4A0.9300
O1—C111.316 (3)C5—C61.484 (3)
O1—H1A0.8200C6—C101.383 (3)
O2—C111.206 (3)C6—C71.391 (3)
O3—C161.205 (3)C7—C81.390 (3)
O4—C161.308 (2)C7—H7A0.9300
O4—H4B0.8200C8—H8A0.9300
N1—C21.326 (3)C9—C101.380 (3)
N1—C31.334 (3)C9—H9A0.9300
N2—C81.322 (3)C10—H10A0.9300
N2—C91.327 (3)C11—C121.486 (3)
C1—C51.383 (3)C12—C131.352 (3)
C1—C21.384 (3)C13—C141.410 (3)
C1—H1B0.9300C13—H13A0.9300
C2—H2B0.9300C14—C151.355 (3)
C3—C41.376 (3)C14—H14A0.9300
C3—H3A0.9300C15—C161.484 (3)
C15—S1—C1291.15 (10)N2—C8—H8A118.4
C11—O1—H1A109.5C7—C8—H8A118.4
C16—O4—H4B109.5N2—C9—C10122.8 (2)
C2—N1—C3117.75 (18)N2—C9—H9A118.6
C8—N2—C9118.2 (2)C10—C9—H9A118.6
C5—C1—C2119.25 (19)C9—C10—C6119.5 (2)
C5—C1—H1B120.4C9—C10—H10A120.3
C2—C1—H1B120.4C6—C10—H10A120.3
N1—C2—C1123.2 (2)O2—C11—O1125.4 (2)
N1—C2—H2B118.4O2—C11—C12122.5 (2)
C1—C2—H2B118.4O1—C11—C12112.1 (2)
N1—C3—C4122.8 (2)C13—C12—C11125.5 (2)
N1—C3—H3A118.6C13—C12—S1111.66 (16)
C4—C3—H3A118.6C11—C12—S1122.88 (18)
C3—C4—C5119.6 (2)C12—C13—C14112.9 (2)
C3—C4—H4A120.2C12—C13—H13A123.5
C5—C4—H4A120.2C14—C13—H13A123.5
C1—C5—C4117.33 (19)C15—C14—C13112.2 (2)
C1—C5—C6121.27 (19)C15—C14—H14A123.9
C4—C5—C6121.4 (2)C13—C14—H14A123.9
C10—C6—C7117.8 (2)C14—C15—C16128.77 (19)
C10—C6—C5121.3 (2)C14—C15—S1112.01 (15)
C7—C6—C5120.9 (2)C16—C15—S1119.22 (16)
C8—C7—C6118.6 (2)O3—C16—O4125.1 (2)
C8—C7—H7A120.7O3—C16—C15122.38 (19)
C6—C7—H7A120.7O4—C16—C15112.52 (18)
N2—C8—C7123.1 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1A···N2i0.821.842.662 (2)175
O4—H4B···N1ii0.821.802.616 (2)175
Symmetry codes: (i) x1, y+1, z+1; (ii) x+1, y1/2, z+1/2.
 

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