Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536803019275/ww6113sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536803019275/ww6113Isup2.hkl |
CCDC reference: 225706
Key indicators
- Single-crystal X-ray study
- T = 295 K
- Mean (C-C) = 0.004 Å
- R factor = 0.034
- wR factor = 0.095
- Data-to-parameter ratio = 14.8
checkCIF/PLATON results
No syntax errors found
Alert level B PLAT230_ALERT_2_B Hirshfeld Test Diff for N1 - C2 = 13.71 su PLAT420_ALERT_2_B D-H Without Acceptor O1W - H1B ... ?
Alert level C PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ? PLAT128_ALERT_4_C Non-standard setting of Space group P21/c .... P21/a PLAT352_ALERT_3_C Short N-H Bond (0.87A) N11 - H11A = 0.74 Ang. PLAT352_ALERT_3_C Short N-H Bond (0.87A) N12 - H12A = 0.72 Ang. PLAT352_ALERT_3_C Short N-H Bond (0.87A) N13 - H13B = 0.71 Ang.
0 ALERT level A = In general: serious problem 2 ALERT level B = Potentially serious problem 5 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 3 ALERT type 3 Indicator that the structure quality may be low 1 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: MSC/AFC Diffractometer Control Software (Molecular Structure Corporation, 1999); cell refinement: MSC/AFC Diffractometer Control Software; data reduction: TEXSAN for Windows (Molecular Structure Corporation, 1999)'; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON for Windows (Spek, 1999); software used to prepare material for publication: PLATON for Windows.
2CH6N3+·C9H4INO4S−·H2O | F(000) = 968 |
Mr = 487.28 | Dx = 1.829 Mg m−3 |
Monoclinic, P21/a | Melting point = 441–445 K |
Hall symbol: -P 2yab | Mo Kα radiation, λ = 0.7107 Å |
a = 22.329 (2) Å | Cell parameters from 25 reflections |
b = 6.9918 (19) Å | θ = 12.5–16.1° |
c = 11.3456 (8) Å | µ = 1.97 mm−1 |
β = 92.646 (7)° | T = 295 K |
V = 1769.4 (5) Å3 | Plate, pale brown |
Z = 4 | 0.50 × 0.50 × 0.20 mm |
Rigaku AFC7R diffractometer | 3559 reflections with I > 2σ(I) |
Radiation source: Rigaku rotating anode | Rint = 0.022 |
Graphite monochromator | θmax = 27.5°, θmin = 2.5° |
ω–2θ scans | h = −10→28 |
Absorption correction: ψ scan TeXsan for Windows (Molecular Structure Corporation, 1999)' | k = 0→9 |
Tmin = 0.398, Tmax = 0.674 | l = −14→14 |
4344 measured reflections | 3 standard reflections every 150 reflections |
4057 independent reflections | intensity decay: 18.9% |
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.034 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.095 | w = 1/[σ2(Fo2) + (0.0541P)2 + 2.4019P] where P = (Fo2 + 2Fc2)/3 |
S = 1.02 | (Δ/σ)max = 0.018 |
4057 reflections | Δρmax = 1.32 e Å−3 |
275 parameters | Δρmin = −1.19 e Å−3 |
0 restraints | Extinction correction: SHELXL97 (Sheldrick, 1997), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.0012 (3) |
Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All e.s.d.'s are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles |
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 | ||
I7 | 0.234933 (10) | −0.20393 (3) | 0.419865 (19) | 0.0396 (1) | |
S5 | 0.41595 (3) | 0.24664 (12) | 0.21790 (7) | 0.0286 (2) | |
O8 | 0.15677 (10) | 0.1141 (4) | 0.2775 (2) | 0.0375 (7) | |
O51 | 0.42226 (11) | 0.2538 (4) | 0.0902 (2) | 0.0371 (7) | |
O52 | 0.43580 (11) | 0.4257 (4) | 0.2724 (2) | 0.0403 (7) | |
O53 | 0.44545 (10) | 0.0795 (4) | 0.2715 (2) | 0.0391 (7) | |
N1 | 0.19050 (12) | 0.4417 (4) | 0.1663 (2) | 0.0351 (8) | |
C2 | 0.20755 (16) | 0.6037 (6) | 0.1100 (3) | 0.0438 (10) | |
C3 | 0.26662 (16) | 0.6509 (6) | 0.0988 (3) | 0.0403 (10) | |
C4 | 0.31098 (15) | 0.5298 (5) | 0.1417 (3) | 0.0357 (9) | |
C5 | 0.33875 (13) | 0.2197 (4) | 0.2409 (3) | 0.0284 (8) | |
C6 | 0.31982 (13) | 0.0601 (5) | 0.2996 (3) | 0.0293 (8) | |
C7 | 0.25883 (13) | 0.0276 (4) | 0.3150 (2) | 0.0280 (8) | |
C8 | 0.21333 (13) | 0.1474 (5) | 0.2685 (2) | 0.0275 (8) | |
C9 | 0.29593 (13) | 0.3570 (5) | 0.1969 (2) | 0.0279 (8) | |
C10 | 0.23374 (14) | 0.3180 (4) | 0.2092 (2) | 0.0275 (8) | |
N11 | 0.07177 (14) | 0.4162 (5) | 0.0563 (3) | 0.0401 (9) | |
N12 | 0.03364 (16) | 0.2393 (6) | −0.1001 (3) | 0.0418 (10) | |
N13 | 0.07837 (16) | 0.0913 (5) | 0.0622 (3) | 0.0425 (10) | |
C11 | 0.06209 (14) | 0.2483 (5) | 0.0046 (3) | 0.0311 (8) | |
N21 | 0.06664 (16) | 0.3266 (5) | 0.3711 (3) | 0.0440 (10) | |
N22 | 0.09874 (18) | 0.1422 (6) | 0.5282 (4) | 0.0551 (11) | |
N23 | 0.00221 (18) | 0.2601 (7) | 0.5170 (4) | 0.0533 (11) | |
C21 | 0.05587 (16) | 0.2394 (5) | 0.4719 (3) | 0.0365 (9) | |
O1W | 0.07994 (15) | 0.7867 (5) | 0.2855 (3) | 0.0653 (11) | |
H2 | 0.177400 | 0.686500 | 0.077200 | 0.0520* | |
H3 | 0.277000 | 0.767400 | 0.061700 | 0.0480* | |
H4 | 0.351800 | 0.562600 | 0.133800 | 0.0430* | |
H6 | 0.348600 | −0.0294 | 0.330100 | 0.0350* | |
H11A | 0.093 (2) | 0.421 (7) | 0.108 (4) | 0.044 (12)* | |
H11B | 0.0686 (18) | 0.513 (6) | 0.012 (3) | 0.035 (10)* | |
H12A | 0.0259 (19) | 0.327 (6) | −0.131 (4) | 0.031 (11)* | |
H12B | 0.026 (2) | 0.140 (8) | −0.128 (4) | 0.053 (14)* | |
H13A | 0.0973 (19) | 0.095 (7) | 0.130 (4) | 0.046 (11)* | |
H13B | 0.0788 (19) | 0.003 (7) | 0.031 (4) | 0.036 (11)* | |
H21A | 0.093 (3) | 0.281 (8) | 0.335 (5) | 0.061 (16)* | |
H21B | 0.038 (3) | 0.370 (8) | 0.327 (5) | 0.066 (15)* | |
H22A | 0.091 (2) | 0.076 (7) | 0.579 (4) | 0.050 (13)* | |
H22B | 0.128 (3) | 0.133 (8) | 0.491 (5) | 0.060 (15)* | |
H23A | −0.005 (2) | 0.207 (7) | 0.587 (5) | 0.058 (14)* | |
H23B | −0.025 (3) | 0.321 (9) | 0.474 (6) | 0.08 (2)* | |
H1A | 0.107 (3) | 0.891 (9) | 0.285 (6) | 0.066 (15)* | |
H1B | 0.105 (4) | 0.681 (9) | 0.293 (7) | 0.076 (14)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
I7 | 0.0391 (2) | 0.0376 (2) | 0.0421 (2) | −0.0032 (1) | 0.0016 (1) | 0.0130 (1) |
S5 | 0.0225 (3) | 0.0317 (4) | 0.0314 (4) | −0.0011 (3) | 0.0003 (3) | −0.0016 (3) |
O8 | 0.0233 (10) | 0.0446 (13) | 0.0445 (12) | −0.0013 (10) | 0.0021 (9) | 0.0071 (11) |
O51 | 0.0362 (12) | 0.0427 (12) | 0.0330 (11) | 0.0010 (10) | 0.0082 (9) | −0.0011 (10) |
O52 | 0.0353 (12) | 0.0396 (13) | 0.0457 (13) | −0.0076 (10) | −0.0028 (10) | −0.0075 (11) |
O53 | 0.0258 (11) | 0.0402 (13) | 0.0509 (13) | 0.0014 (10) | −0.0036 (9) | 0.0063 (11) |
N1 | 0.0291 (13) | 0.0392 (15) | 0.0365 (13) | 0.0049 (11) | −0.0030 (10) | 0.0074 (12) |
C2 | 0.0320 (16) | 0.053 (2) | 0.0450 (18) | 0.0159 (16) | −0.0121 (14) | −0.0071 (16) |
C3 | 0.0432 (19) | 0.0364 (17) | 0.0417 (17) | 0.0015 (14) | 0.0057 (14) | 0.0125 (15) |
C4 | 0.0320 (15) | 0.0393 (17) | 0.0363 (15) | 0.0011 (13) | 0.0061 (12) | 0.0066 (13) |
C5 | 0.0247 (13) | 0.0335 (15) | 0.0271 (13) | 0.0004 (11) | 0.0009 (11) | −0.0006 (11) |
C6 | 0.0282 (14) | 0.0319 (15) | 0.0276 (13) | 0.0023 (12) | −0.0013 (11) | 0.0023 (12) |
C7 | 0.0303 (14) | 0.0298 (14) | 0.0238 (12) | −0.0011 (12) | 0.0003 (10) | 0.0024 (11) |
C8 | 0.0260 (14) | 0.0343 (15) | 0.0222 (12) | −0.0016 (12) | 0.0017 (10) | −0.0026 (11) |
C9 | 0.0281 (14) | 0.0315 (15) | 0.0240 (12) | 0.0032 (12) | 0.0004 (10) | 0.0003 (11) |
C10 | 0.0281 (14) | 0.0306 (15) | 0.0234 (12) | 0.0031 (11) | −0.0017 (10) | 0.0002 (11) |
N11 | 0.0391 (16) | 0.0363 (16) | 0.0440 (16) | −0.0010 (13) | −0.0082 (13) | 0.0017 (14) |
N12 | 0.0471 (18) | 0.0424 (18) | 0.0349 (15) | 0.0042 (15) | −0.0077 (13) | −0.0007 (15) |
N13 | 0.0548 (19) | 0.0331 (16) | 0.0392 (16) | 0.0045 (14) | −0.0024 (14) | 0.0025 (14) |
C11 | 0.0240 (14) | 0.0369 (16) | 0.0323 (14) | 0.0007 (12) | 0.0018 (11) | 0.0004 (13) |
N21 | 0.0361 (16) | 0.0521 (19) | 0.0438 (16) | 0.0065 (14) | 0.0026 (14) | 0.0074 (15) |
N22 | 0.0442 (19) | 0.067 (2) | 0.054 (2) | −0.0010 (18) | 0.0011 (16) | 0.0229 (19) |
N23 | 0.0421 (19) | 0.068 (2) | 0.051 (2) | −0.0082 (18) | 0.0144 (16) | −0.0114 (19) |
C21 | 0.0312 (16) | 0.0401 (17) | 0.0381 (16) | −0.0070 (13) | −0.0004 (13) | −0.0050 (14) |
O1W | 0.0522 (18) | 0.073 (2) | 0.070 (2) | −0.0202 (16) | −0.0062 (15) | 0.0143 (17) |
I7—C7 | 2.093 (3) | N23—C21 | 1.332 (5) |
S5—O51 | 1.463 (2) | N21—H21B | 0.85 (6) |
S5—O52 | 1.456 (3) | N21—H21A | 0.80 (6) |
S5—O53 | 1.460 (3) | N22—H22A | 0.77 (5) |
S5—C5 | 1.765 (3) | N22—H22B | 0.80 (6) |
O8—C8 | 1.293 (4) | N23—H23B | 0.87 (7) |
O1W—H1B | 0.93 (7) | N23—H23A | 0.90 (6) |
O1W—H1A | 0.94 (5) | C2—C3 | 1.371 (5) |
N1—C10 | 1.369 (4) | C3—C4 | 1.375 (5) |
N1—C2 | 1.363 (5) | C4—C9 | 1.409 (5) |
N11—C11 | 1.326 (5) | C5—C9 | 1.429 (4) |
N12—C11 | 1.322 (5) | C5—C6 | 1.376 (5) |
N13—C11 | 1.320 (5) | C6—C7 | 1.400 (4) |
N11—H11B | 0.84 (4) | C7—C8 | 1.401 (4) |
N11—H11A | 0.74 (5) | C8—C10 | 1.453 (4) |
N12—H12B | 0.78 (5) | C9—C10 | 1.428 (4) |
N12—H12A | 0.72 (4) | C2—H2 | 0.9506 |
N13—H13A | 0.86 (4) | C3—H3 | 0.9505 |
N13—H13B | 0.71 (5) | C4—H4 | 0.9481 |
N21—C21 | 1.328 (5) | C6—H6 | 0.9507 |
N22—C21 | 1.315 (5) | ||
O51—S5—O52 | 110.47 (15) | S5—C5—C6 | 118.8 (2) |
O51—S5—O53 | 112.18 (15) | S5—C5—C9 | 121.3 (2) |
O51—S5—C5 | 106.82 (15) | C5—C6—C7 | 121.0 (3) |
O52—S5—O53 | 112.86 (15) | C6—C7—C8 | 123.3 (3) |
O52—S5—C5 | 108.00 (14) | I7—C7—C6 | 118.1 (2) |
O53—S5—C5 | 106.13 (14) | I7—C7—C8 | 118.5 (2) |
H1A—O1W—H1B | 103 (6) | C7—C8—C10 | 115.3 (3) |
C2—N1—C10 | 118.9 (3) | O8—C8—C7 | 123.8 (3) |
C11—N11—H11B | 116 (3) | O8—C8—C10 | 120.8 (3) |
H11A—N11—H11B | 118 (5) | C4—C9—C5 | 124.2 (3) |
C11—N11—H11A | 119 (4) | C4—C9—C10 | 117.4 (3) |
C11—N12—H12B | 120 (4) | C5—C9—C10 | 118.4 (3) |
H12A—N12—H12B | 121 (5) | N1—C10—C8 | 116.9 (3) |
C11—N12—H12A | 119 (4) | C8—C10—C9 | 121.9 (3) |
C11—N13—H13B | 119 (4) | N1—C10—C9 | 121.2 (3) |
H13A—N13—H13B | 117 (5) | N1—C2—H2 | 118.77 |
C11—N13—H13A | 122 (3) | C3—C2—H2 | 118.95 |
C21—N21—H21B | 121 (4) | C4—C3—H3 | 119.87 |
C21—N21—H21A | 115 (4) | C2—C3—H3 | 120.17 |
H21A—N21—H21B | 113 (6) | C3—C4—H4 | 119.84 |
H22A—N22—H22B | 125 (5) | C9—C4—H4 | 119.97 |
C21—N22—H22B | 112 (4) | C7—C6—H6 | 119.54 |
C21—N22—H22A | 120 (3) | C5—C6—H6 | 119.50 |
C21—N23—H23B | 117 (4) | N11—C11—N12 | 120.1 (3) |
C21—N23—H23A | 120 (3) | N11—C11—N13 | 118.8 (3) |
H23A—N23—H23B | 123 (5) | N12—C11—N13 | 121.0 (4) |
N1—C2—C3 | 122.3 (3) | N21—C21—N22 | 119.9 (4) |
C2—C3—C4 | 120.0 (4) | N21—C21—N23 | 118.9 (4) |
C3—C4—C9 | 120.2 (3) | N22—C21—N23 | 121.1 (4) |
C6—C5—C9 | 119.9 (3) | ||
O51—S5—C5—C6 | 119.5 (3) | S5—C5—C6—C7 | −176.9 (2) |
O51—S5—C5—C9 | −58.6 (3) | C6—C5—C9—C10 | −3.7 (4) |
O52—S5—C5—C6 | −121.6 (3) | C5—C6—C7—C8 | 2.9 (5) |
O52—S5—C5—C9 | 60.2 (3) | C5—C6—C7—I7 | −173.9 (2) |
O53—S5—C5—C6 | −0.3 (3) | I7—C7—C8—O8 | −6.5 (4) |
O53—S5—C5—C9 | −178.5 (2) | C6—C7—C8—O8 | 176.7 (3) |
C10—N1—C2—C3 | −2.6 (5) | C6—C7—C8—C10 | −4.2 (4) |
C2—N1—C10—C8 | 180.00 (1) | I7—C7—C8—C10 | 172.62 (17) |
C2—N1—C10—C9 | 0.6 (4) | O8—C8—C10—N1 | 1.4 (4) |
N1—C2—C3—C4 | 2.2 (5) | O8—C8—C10—C9 | −179.3 (2) |
C2—C3—C4—C9 | 0.2 (5) | C7—C8—C10—C9 | 1.6 (4) |
C3—C4—C9—C5 | 178.0 (3) | C7—C8—C10—N1 | −177.8 (2) |
C3—C4—C9—C10 | −2.0 (4) | C4—C9—C10—N1 | 1.6 (4) |
C9—C5—C6—C7 | 1.3 (5) | C5—C9—C10—N1 | −178.4 (3) |
S5—C5—C9—C4 | −5.6 (4) | C5—C9—C10—C8 | 2.3 (4) |
S5—C5—C9—C10 | 174.4 (2) | C4—C9—C10—C8 | −177.7 (3) |
C6—C5—C9—C4 | 176.3 (3) |
D—H···A | D—H | H···A | D···A | D—H···A |
O1W—H1A···O8i | 0.95 (6) | 1.92 (6) | 2.865 (4) | 175 (6) |
N11—H11A···N1 | 0.74 (5) | 2.25 (4) | 2.883 (4) | 144 (4) |
N11—H11B···O51ii | 0.84 (4) | 2.06 (4) | 2.894 (4) | 169 (4) |
N12—H12A···O53ii | 0.72 (4) | 2.48 (4) | 3.121 (5) | 148 (4) |
N12—H12B···O52iii | 0.78 (5) | 2.41 (5) | 3.036 (5) | 139 (4) |
N13—H13A···O8 | 0.86 (4) | 2.09 (4) | 2.943 (4) | 170 (4) |
N13—H13B···O51iii | 0.71 (5) | 2.22 (5) | 2.925 (4) | 171 (5) |
N21—H21A···O8 | 0.80 (6) | 1.98 (6) | 2.754 (4) | 165 (6) |
N21—H21B···O53iv | 0.85 (6) | 2.16 (7) | 2.958 (4) | 156 (6) |
N22—H22A···O52v | 0.77 (5) | 2.10 (5) | 2.858 (5) | 172 (5) |
N22—H22B···O8 | 0.80 (6) | 2.54 (6) | 3.186 (5) | 139 (6) |
N23—H23A···O1Wvi | 0.90 (6) | 2.26 (5) | 2.979 (6) | 137 (4) |
N23—H23B···O53iv | 0.87 (7) | 2.46 (7) | 3.209 (5) | 144 (6) |
C4—H4···O52 | 0.9481 | 2.5758 | 3.180 (4) | 121.91 |
C6—H6···O53 | 0.9507 | 2.4148 | 2.841 (4) | 106.93 |
Symmetry codes: (i) x, y+1, z; (ii) −x+1/2, y+1/2, −z; (iii) −x+1/2, y−1/2, −z; (iv) x−1/2, −y+1/2, z; (v) −x+1/2, y−1/2, −z+1; (vi) −x, −y+1, −z+1. |
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