Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536804021087/wn6275sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536804021087/wn6275Isup2.hkl |
CCDC reference: 252959
Key indicators
- Single-crystal X-ray study
- T = 300 K
- Mean (C-C) = 0.004 Å
- R factor = 0.051
- wR factor = 0.119
- Data-to-parameter ratio = 16.0
checkCIF/PLATON results
No syntax errors found
Alert level C PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ? PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor .... 2.18 PLAT371_ALERT_2_C Long C(sp2)-C(sp1) Bond C9 - C13 ... 1.44 Ang.
0 ALERT level A = In general: serious problem 0 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 0 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: MSC/AFC Diffractometer Control Software (Molecular Structure Corporation, 1990); cell refinement: MSC/AFC Diffractometer Control Software; data reduction: TEXSAN for Windows (Molecular Structure Corporation, 1997-1999); program(s) used to solve structure: SIR92 (Altomare et al., 1994); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: PLATON (Spek, 2003).
C6H4N2·C7H4ClNO4 | F(000) = 624.0 |
Mr = 305.67 | Dx = 1.504 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2yn | Cell parameters from 25 reflections |
a = 10.012 (3) Å | θ = 11.5–12.1° |
b = 10.318 (3) Å | µ = 0.30 mm−1 |
c = 13.974 (2) Å | T = 300 K |
β = 110.767 (15)° | Prism, colorless |
V = 1349.7 (6) Å3 | 0.40 × 0.30 × 0.30 mm |
Z = 4 |
Rigaku AFC-5R diffractometer | 1692 reflections with I > 2σ(I) |
Radiation source: Rigaku rotating anode | Rint = 0.021 |
Graphite monochromator | θmax = 27.5°, θmin = 2.2° |
ω–2θ scans | h = −1→13 |
Absorption correction: ψ scan (North et al., 1968) | k = 0→13 |
Tmin = 0.898, Tmax = 0.915 | l = −18→17 |
3633 measured reflections | 3 standard reflections every 97 reflections |
3103 independent reflections | intensity decay: 4.8% |
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)] = 0.051 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.119 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.01 | w = 1/[σ2(Fo2) + (0.04P)2 + 0.45P] where P = (Fo2 + 2Fc2)/3 |
3103 reflections | (Δ/σ)max = 0.001 |
194 parameters | Δρmax = 0.23 e Å−3 |
0 restraints | Δρmin = −0.25 e Å−3 |
0 constraints |
Experimental. The scan width was (1.68 + 0.30tanθ)° with an ω scan speed of 6° per minute (up to 3 scans to achieve I/σ(I) > 10). Stationary background counts were recorded at each end of the scan, and the scan time:background time ratio was 2:1. |
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. |
x | y | z | Uiso*/Ueq | ||
Cl | 0.24621 (11) | 0.60956 (8) | 0.08116 (6) | 0.0770 (3) | |
O1 | 0.4477 (2) | 0.29136 (19) | 0.24162 (13) | 0.0619 (6) | |
O2 | 0.5200 (2) | 0.4925 (2) | 0.23403 (14) | 0.0597 (6) | |
O3 | 0.1397 (2) | 0.4539 (2) | −0.29062 (14) | 0.0637 (6) | |
O4 | 0.2499 (2) | 0.2733 (2) | −0.28571 (13) | 0.0625 (6) | |
N1 | 0.2182 (3) | 0.3664 (2) | −0.24438 (16) | 0.0472 (6) | |
N2 | 0.6406 (2) | 0.4696 (2) | 0.43469 (15) | 0.0452 (6) | |
N3 | 0.5637 (3) | 0.1709 (3) | 0.6690 (2) | 0.0819 (10) | |
C1 | 0.3913 (3) | 0.3872 (2) | 0.07832 (17) | 0.0380 (6) | |
C2 | 0.2977 (3) | 0.4822 (2) | 0.02162 (18) | 0.0434 (7) | |
C3 | 0.2399 (3) | 0.4758 (3) | −0.08426 (18) | 0.0454 (7) | |
C4 | 0.2784 (3) | 0.3730 (3) | −0.13161 (16) | 0.0389 (6) | |
C5 | 0.3696 (3) | 0.2777 (3) | −0.07910 (18) | 0.0444 (7) | |
C6 | 0.4245 (3) | 0.2853 (3) | 0.02654 (18) | 0.0442 (7) | |
C7 | 0.4549 (3) | 0.3859 (3) | 0.19374 (17) | 0.0411 (6) | |
C8 | 0.6006 (3) | 0.3731 (3) | 0.48122 (18) | 0.0432 (7) | |
C9 | 0.6538 (3) | 0.3595 (3) | 0.58716 (19) | 0.0420 (6) | |
C10 | 0.7534 (3) | 0.4475 (3) | 0.64607 (19) | 0.0475 (7) | |
C11 | 0.7945 (3) | 0.5465 (3) | 0.59704 (19) | 0.0504 (7) | |
C12 | 0.7353 (3) | 0.5546 (3) | 0.4918 (2) | 0.0499 (7) | |
C13 | 0.6048 (3) | 0.2544 (3) | 0.6336 (2) | 0.0545 (8) | |
H1 | 0.564 (4) | 0.480 (4) | 0.307 (3) | 0.127 (15)* | |
H2 | 0.1770 | 0.5389 | −0.1221 | 0.055* | |
H3 | 0.3942 | 0.2097 | −0.1134 | 0.053* | |
H4 | 0.4853 | 0.2203 | 0.0636 | 0.053* | |
H5 | 0.5351 | 0.3127 | 0.4419 | 0.052* | |
H6 | 0.7913 | 0.4398 | 0.7170 | 0.057* | |
H7 | 0.8615 | 0.6072 | 0.6342 | 0.060* | |
H8 | 0.7629 | 0.6227 | 0.4593 | 0.060* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Cl | 0.1210 (8) | 0.0572 (5) | 0.0425 (4) | 0.0305 (5) | 0.0164 (4) | −0.0053 (4) |
O1 | 0.0881 (16) | 0.0538 (13) | 0.0338 (10) | −0.0154 (12) | 0.0093 (10) | 0.0049 (9) |
O2 | 0.0802 (15) | 0.0563 (13) | 0.0299 (9) | −0.0255 (12) | 0.0039 (10) | 0.0005 (9) |
O3 | 0.0755 (15) | 0.0686 (14) | 0.0329 (10) | 0.0061 (13) | 0.0018 (10) | 0.0079 (10) |
O4 | 0.0776 (16) | 0.0683 (14) | 0.0360 (10) | −0.0002 (12) | 0.0134 (10) | −0.0150 (10) |
N1 | 0.0515 (16) | 0.0566 (15) | 0.0287 (10) | −0.0131 (13) | 0.0082 (10) | −0.0025 (11) |
N2 | 0.0504 (15) | 0.0527 (14) | 0.0288 (10) | −0.0004 (12) | 0.0095 (10) | 0.0005 (10) |
N3 | 0.084 (2) | 0.090 (2) | 0.0625 (18) | −0.0195 (18) | 0.0151 (16) | 0.0241 (16) |
C1 | 0.0415 (15) | 0.0423 (14) | 0.0269 (11) | −0.0074 (13) | 0.0081 (11) | 0.0031 (11) |
C2 | 0.0588 (18) | 0.0379 (14) | 0.0318 (12) | −0.0008 (14) | 0.0140 (12) | −0.0024 (11) |
C3 | 0.0549 (18) | 0.0440 (15) | 0.0314 (12) | 0.0048 (14) | 0.0079 (12) | 0.0039 (12) |
C4 | 0.0411 (15) | 0.0470 (16) | 0.0244 (11) | −0.0105 (13) | 0.0066 (11) | −0.0008 (11) |
C5 | 0.0448 (17) | 0.0503 (16) | 0.0365 (13) | 0.0024 (14) | 0.0123 (12) | −0.0063 (12) |
C6 | 0.0407 (16) | 0.0522 (17) | 0.0343 (13) | 0.0056 (14) | 0.0066 (12) | 0.0043 (12) |
C7 | 0.0434 (16) | 0.0488 (16) | 0.0288 (12) | −0.0031 (14) | 0.0099 (11) | −0.0008 (12) |
C8 | 0.0443 (17) | 0.0468 (16) | 0.0341 (12) | 0.0037 (13) | 0.0083 (12) | −0.0009 (12) |
C9 | 0.0430 (16) | 0.0472 (16) | 0.0365 (13) | 0.0067 (13) | 0.0151 (12) | 0.0054 (12) |
C10 | 0.0535 (19) | 0.0556 (18) | 0.0285 (12) | 0.0066 (15) | 0.0086 (13) | 0.0003 (12) |
C11 | 0.0542 (18) | 0.0552 (17) | 0.0354 (14) | −0.0070 (15) | 0.0080 (13) | −0.0051 (13) |
C12 | 0.060 (2) | 0.0495 (17) | 0.0396 (14) | −0.0048 (15) | 0.0166 (14) | 0.0028 (13) |
C13 | 0.057 (2) | 0.060 (2) | 0.0409 (15) | 0.0006 (16) | 0.0108 (14) | 0.0069 (14) |
Cl—C2 | 1.729 (3) | N2—C12 | 1.330 (3) |
O1—C7 | 1.200 (3) | N3—C13 | 1.140 (4) |
O2—C7 | 1.300 (3) | C8—C9 | 1.391 (3) |
O2—H1 | 0.96 (4) | C9—C10 | 1.383 (4) |
O3—N1 | 1.221 (3) | C9—C13 | 1.437 (4) |
O4—N1 | 1.220 (3) | C10—C11 | 1.372 (4) |
N1—C4 | 1.476 (3) | C11—C12 | 1.379 (3) |
C1—C6 | 1.381 (4) | C3—H2 | 0.93 |
C1—C2 | 1.394 (3) | C5—H3 | 0.93 |
C1—C7 | 1.509 (3) | C6—H4 | 0.93 |
C2—C3 | 1.386 (3) | C8—H5 | 0.93 |
C3—C4 | 1.375 (4) | C10—H6 | 0.93 |
C4—C5 | 1.366 (4) | C11—H7 | 0.93 |
C5—C6 | 1.383 (3) | C12—H8 | 0.93 |
N2—C8 | 1.326 (3) | ||
O1···N1i | 3.106 (4) | O2···C4ii | 3.178 (4) |
O2···N2 | 2.641 (3) | O2···O4ii | 3.239 (3) |
O2···N1ii | 2.957 (4) | ||
C7—O2—H1 | 108 (3) | C1—C6—H4 | 119.2 |
O4—N1—O3 | 124.0 (2) | C5—C6—H4 | 119.2 |
O4—N1—C4 | 117.8 (2) | O1—C7—O2 | 124.5 (2) |
O3—N1—C4 | 118.3 (2) | O1—C7—C1 | 121.1 (2) |
C8—N2—C12 | 118.4 (2) | O2—C7—C1 | 114.3 (2) |
C6—C1—C2 | 118.4 (2) | N2—C8—C9 | 121.9 (3) |
C6—C1—C7 | 117.7 (2) | N2—C8—H5 | 119.0 |
C2—C1—C7 | 123.8 (2) | C9—C8—H5 | 119.0 |
C3—C2—C1 | 121.0 (2) | C10—C9—C8 | 119.4 (3) |
C3—C2—Cl | 117.9 (2) | C10—C9—C13 | 121.1 (2) |
C1—C2—Cl | 121.10 (19) | C8—C9—C13 | 119.6 (3) |
C4—C3—C2 | 117.9 (2) | C11—C10—C9 | 118.2 (2) |
C4—C3—H2 | 121.0 | C11—C10—H6 | 120.9 |
C2—C3—H2 | 121.0 | C9—C10—H6 | 120.9 |
C5—C4—C3 | 123.0 (2) | C10—C11—C12 | 119.1 (3) |
C5—C4—N1 | 118.9 (2) | C10—C11—H7 | 120.5 |
C3—C4—N1 | 118.1 (2) | C12—C11—H7 | 120.5 |
C4—C5—C6 | 118.0 (2) | N2—C12—C11 | 123.0 (3) |
C4—C5—H3 | 121.0 | N2—C12—H8 | 118.5 |
C6—C5—H3 | 121.0 | C11—C12—H8 | 118.5 |
C1—C6—C5 | 121.6 (3) | N3—C13—C9 | 178.8 (3) |
C6—C1—C2—C3 | −0.5 (4) | C7—C1—C6—C5 | 179.1 (3) |
C7—C1—C2—C3 | −178.1 (3) | C4—C5—C6—C1 | −1.4 (4) |
C6—C1—C2—Cl | 177.7 (2) | C6—C1—C7—O1 | −49.3 (4) |
C7—C1—C2—Cl | 0.1 (4) | C2—C1—C7—O1 | 128.3 (3) |
C1—C2—C3—C4 | −0.3 (4) | C6—C1—C7—O2 | 128.5 (3) |
Cl—C2—C3—C4 | −178.6 (2) | C2—C1—C7—O2 | −53.9 (4) |
C2—C3—C4—C5 | 0.4 (4) | C12—N2—C8—C9 | 0.6 (4) |
C2—C3—C4—N1 | −179.4 (2) | N2—C8—C9—C10 | −1.2 (4) |
O4—N1—C4—C5 | 2.1 (4) | N2—C8—C9—C13 | 178.9 (3) |
O3—N1—C4—C5 | −178.1 (3) | C8—C9—C10—C11 | 0.8 (4) |
O4—N1—C4—C3 | −178.2 (2) | C13—C9—C10—C11 | −179.3 (3) |
O3—N1—C4—C3 | 1.7 (4) | C9—C10—C11—C12 | 0.2 (4) |
C3—C4—C5—C6 | 0.4 (4) | C8—N2—C12—C11 | 0.5 (4) |
N1—C4—C5—C6 | −179.8 (2) | C10—C11—C12—N2 | −0.9 (5) |
C2—C1—C6—C5 | 1.4 (4) |
Symmetry codes: (i) x+1/2, −y+1/2, z+1/2; (ii) −x+1, −y+1, −z. |
D—H···A | D—H | H···A | D···A | D—H···A |
O2—H1···N2 | 0.97 (4) | 1.68 (4) | 2.641 (3) | 176 (4) |