Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270110022328/gd3347sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S0108270110022328/gd3347Isup2.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S0108270110022328/gd3347IIsup3.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S0108270110022328/gd3347IIIsup4.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S0108270110022328/gd3347IVsup5.hkl |
CCDC references: 786826; 786827; 786828; 786829
For all compounds, data collection: CrysAlis PRO (Oxford Diffraction, 2009); cell refinement: CrysAlis PRO (Oxford Diffraction, 2009); data reduction: CrysAlis PRO (Oxford Diffraction, 2009). Program(s) used to solve structure: SHELXS97 (Sheldrick, 2008) for (I), (II), (IV); SIR92 (Altomare et al., 1994) for (III). For all compounds, program(s) used to refine structure: SHELXL97 (Sheldrick, 2008) within WinGX (Farrugia, 1999); molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: PLATON (Spek, 2009).
C6H16N+·C8H3Cl2O4− | F(000) = 704 |
Mr = 336.20 | Dx = 1.411 Mg m−3 |
Monoclinic, P21/c | Melting point: 353 K |
Hall symbol: -P 2ybc | Mo Kα radiation, λ = 0.71073 Å |
a = 7.3206 (7) Å | Cell parameters from 5117 reflections |
b = 11.2201 (7) Å | θ = 3.2–28.8° |
c = 19.4813 (12) Å | µ = 0.42 mm−1 |
β = 98.576 (7)° | T = 200 K |
V = 1582.3 (2) Å3 | Block, colourless |
Z = 4 | 0.40 × 0.40 × 0.30 mm |
Oxford Diffraction Gemini-S CCD-detector diffractometer | 3098 independent reflections |
Radiation source: Enhance (Mo) X-ray source | 2638 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.020 |
Detector resolution: 16.077 pixels mm-1 | θmax = 26.0°, θmin = 3.3° |
ω scans | h = −9→9 |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | k = −13→13 |
Tmin = 0.96, Tmax = 0.98 | l = −20→24 |
10740 measured reflections |
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)] = 0.029 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.077 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.04 | w = 1/[σ2(Fo2) + (0.0454P)2 + 0.1656P] where P = (Fo2 + 2Fc2)/3 |
3098 reflections | (Δ/σ)max = 0.001 |
193 parameters | Δρmax = 0.23 e Å−3 |
0 restraints | Δρmin = −0.24 e Å−3 |
Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su'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 | ||
N1A | −0.05058 (17) | 0.95062 (10) | 0.36011 (6) | 0.0229 (3) | |
C1A | −0.2461 (2) | 0.91354 (14) | 0.36217 (7) | 0.0304 (4) | |
C1B | −0.0117 (2) | 1.07979 (12) | 0.37870 (7) | 0.0258 (4) | |
C1C | 0.0049 (2) | 0.91522 (13) | 0.29175 (7) | 0.0298 (4) | |
C2A | −0.3021 (2) | 0.92226 (15) | 0.43354 (8) | 0.0374 (5) | |
C2B | −0.1025 (2) | 1.16623 (13) | 0.32431 (8) | 0.0380 (5) | |
C2C | 0.2047 (3) | 0.94008 (18) | 0.28776 (10) | 0.0481 (6) | |
Cl4 | 0.57140 (5) | 0.69357 (4) | 0.68165 (2) | 0.0346 (1) | |
Cl5 | 0.53419 (6) | 0.40824 (4) | 0.68041 (2) | 0.0382 (1) | |
O11 | 0.15312 (15) | 0.31238 (9) | 0.44967 (5) | 0.0364 (4) | |
O12 | 0.05781 (15) | 0.46504 (9) | 0.38294 (5) | 0.0328 (3) | |
O21 | 0.05047 (15) | 0.68027 (9) | 0.39185 (5) | 0.0349 (3) | |
O22 | 0.18100 (15) | 0.82561 (9) | 0.45818 (5) | 0.0353 (3) | |
C1 | 0.24055 (17) | 0.50253 (13) | 0.49736 (6) | 0.0205 (4) | |
C2 | 0.25130 (17) | 0.62848 (12) | 0.49892 (6) | 0.0209 (4) | |
C3 | 0.35682 (17) | 0.68325 (13) | 0.55642 (6) | 0.0231 (4) | |
C4 | 0.44516 (18) | 0.61823 (13) | 0.61229 (7) | 0.0238 (4) | |
C5 | 0.42972 (18) | 0.49501 (13) | 0.61168 (7) | 0.0242 (4) | |
C6 | 0.33008 (18) | 0.43895 (12) | 0.55450 (7) | 0.0235 (4) | |
C11 | 0.14444 (19) | 0.41945 (13) | 0.44043 (7) | 0.0252 (4) | |
C21 | 0.15512 (18) | 0.71762 (13) | 0.44567 (7) | 0.0248 (4) | |
H1A | 0.019 (2) | 0.9082 (14) | 0.3943 (8) | 0.0300* | |
H12 | 0.057 (3) | 0.553 (2) | 0.3840 (11) | 0.0590* | |
H11A | −0.26240 | 0.83020 | 0.34570 | 0.0370* | |
H11B | 0.12350 | 1.09290 | 0.38540 | 0.0310* | |
H11C | −0.07280 | 0.95900 | 0.25400 | 0.0360* | |
H12A | −0.32940 | 0.96440 | 0.32980 | 0.0370* | |
H12B | −0.05570 | 1.09700 | 0.42330 | 0.0310* | |
H12C | −0.01900 | 0.82900 | 0.28420 | 0.0360* | |
H21A | −0.42860 | 0.89250 | 0.43190 | 0.0450* | |
H21B | −0.07430 | 1.24810 | 0.33990 | 0.0460* | |
H21C | 0.23690 | 0.90650 | 0.24470 | 0.0580* | |
H22A | −0.29630 | 1.00560 | 0.44870 | 0.0450* | |
H22B | −0.23660 | 1.15410 | 0.31740 | 0.0460* | |
H22C | 0.28200 | 0.90360 | 0.32760 | 0.0580* | |
H23A | −0.21790 | 0.87430 | 0.46630 | 0.0450* | |
H23B | −0.05540 | 1.15240 | 0.28050 | 0.0460* | |
H23C | 0.22540 | 1.02640 | 0.28840 | 0.0580* | |
H3 | 0.36810 | 0.76760 | 0.55710 | 0.0280* | |
H6 | 0.32240 | 0.35440 | 0.55410 | 0.0280* |
U11 | U22 | U33 | U12 | U13 | U23 | |
N1A | 0.0293 (6) | 0.0191 (6) | 0.0185 (6) | 0.0008 (5) | −0.0022 (5) | 0.0005 (4) |
C1A | 0.0313 (8) | 0.0307 (8) | 0.0272 (7) | −0.0049 (7) | −0.0021 (6) | 0.0022 (6) |
C1B | 0.0321 (8) | 0.0196 (7) | 0.0238 (7) | −0.0011 (6) | −0.0019 (6) | −0.0029 (5) |
C1C | 0.0405 (8) | 0.0257 (8) | 0.0226 (7) | 0.0003 (7) | 0.0025 (6) | −0.0042 (6) |
C2A | 0.0417 (9) | 0.0357 (9) | 0.0359 (9) | −0.0040 (7) | 0.0094 (7) | 0.0008 (7) |
C2B | 0.0562 (11) | 0.0200 (8) | 0.0330 (8) | 0.0028 (7) | −0.0090 (7) | −0.0008 (6) |
C2C | 0.0459 (10) | 0.0582 (12) | 0.0430 (10) | −0.0003 (9) | 0.0157 (8) | −0.0085 (8) |
Cl4 | 0.0363 (2) | 0.0381 (2) | 0.0258 (2) | 0.0023 (2) | −0.0076 (2) | −0.0071 (2) |
Cl5 | 0.0447 (2) | 0.0362 (2) | 0.0302 (2) | 0.0083 (2) | −0.0055 (2) | 0.0104 (2) |
O11 | 0.0458 (7) | 0.0219 (6) | 0.0389 (6) | −0.0040 (5) | −0.0018 (5) | −0.0034 (4) |
O12 | 0.0449 (6) | 0.0271 (6) | 0.0237 (5) | −0.0006 (5) | −0.0036 (5) | −0.0044 (4) |
O21 | 0.0455 (6) | 0.0284 (6) | 0.0260 (5) | 0.0022 (5) | −0.0105 (5) | 0.0009 (4) |
O22 | 0.0458 (6) | 0.0211 (6) | 0.0344 (6) | 0.0010 (5) | −0.0091 (5) | 0.0030 (4) |
C1 | 0.0183 (6) | 0.0232 (7) | 0.0208 (7) | 0.0015 (6) | 0.0052 (5) | −0.0005 (5) |
C2 | 0.0209 (7) | 0.0222 (7) | 0.0197 (7) | 0.0015 (5) | 0.0037 (5) | −0.0002 (5) |
C3 | 0.0253 (7) | 0.0204 (7) | 0.0233 (7) | 0.0015 (6) | 0.0026 (5) | −0.0013 (5) |
C4 | 0.0212 (7) | 0.0286 (8) | 0.0208 (7) | 0.0026 (6) | 0.0009 (5) | −0.0040 (6) |
C5 | 0.0229 (7) | 0.0283 (8) | 0.0211 (7) | 0.0050 (6) | 0.0020 (5) | 0.0044 (6) |
C6 | 0.0245 (7) | 0.0203 (7) | 0.0265 (7) | 0.0019 (6) | 0.0061 (6) | 0.0017 (5) |
C11 | 0.0245 (7) | 0.0259 (8) | 0.0257 (7) | −0.0014 (6) | 0.0057 (6) | −0.0022 (6) |
C21 | 0.0266 (7) | 0.0239 (8) | 0.0234 (7) | 0.0034 (6) | 0.0026 (6) | 0.0018 (6) |
Cl4—C4 | 1.7383 (14) | C2A—H21A | 0.9800 |
Cl5—C5 | 1.7378 (14) | C2A—H22A | 0.9800 |
O11—C11 | 1.2150 (18) | C2A—H23A | 0.9800 |
O12—C11 | 1.3063 (17) | C2B—H21B | 0.9800 |
O21—C21 | 1.2737 (17) | C2B—H22B | 0.9800 |
O22—C21 | 1.2448 (18) | C2B—H23B | 0.9800 |
O12—H12 | 0.99 (2) | C2C—H21C | 0.9800 |
N1A—C1A | 1.4968 (19) | C2C—H22C | 0.9800 |
N1A—C1B | 1.5106 (18) | C2C—H23C | 0.9800 |
N1A—C1C | 1.5025 (18) | C1—C2 | 1.415 (2) |
N1A—H1A | 0.910 (15) | C1—C11 | 1.5366 (19) |
C1A—C2A | 1.510 (2) | C1—C6 | 1.4000 (18) |
C1B—C2B | 1.515 (2) | C2—C3 | 1.4040 (17) |
C1C—C2C | 1.502 (3) | C2—C21 | 1.5344 (19) |
C1A—H12A | 0.9900 | C3—C4 | 1.3875 (19) |
C1A—H11A | 0.9900 | C4—C5 | 1.387 (2) |
C1B—H11B | 0.9900 | C5—C6 | 1.3879 (19) |
C1B—H12B | 0.9900 | C3—H3 | 0.9500 |
C1C—H12C | 0.9900 | C6—H6 | 0.9500 |
C1C—H11C | 0.9900 | ||
C11—O12—H12 | 112.2 (12) | H21B—C2B—H23B | 109.00 |
C1A—N1A—C1C | 109.65 (11) | H22B—C2B—H23B | 110.00 |
C1B—N1A—C1C | 113.58 (11) | C1B—C2B—H22B | 109.00 |
C1A—N1A—C1B | 114.02 (11) | C1C—C2C—H21C | 109.00 |
C1B—N1A—H1A | 105.2 (10) | C1C—C2C—H23C | 109.00 |
C1C—N1A—H1A | 108.3 (10) | H21C—C2C—H22C | 109.00 |
C1A—N1A—H1A | 105.6 (9) | C1C—C2C—H22C | 109.00 |
N1A—C1A—C2A | 113.49 (12) | H22C—C2C—H23C | 109.00 |
N1A—C1B—C2B | 113.53 (11) | H21C—C2C—H23C | 110.00 |
N1A—C1C—C2C | 113.00 (13) | C2—C1—C6 | 118.28 (11) |
N1A—C1A—H12A | 109.00 | C2—C1—C11 | 129.73 (11) |
C2A—C1A—H11A | 109.00 | C6—C1—C11 | 111.99 (12) |
C2A—C1A—H12A | 109.00 | C1—C2—C3 | 118.45 (11) |
H11A—C1A—H12A | 108.00 | C1—C2—C21 | 128.16 (11) |
N1A—C1A—H11A | 109.00 | C3—C2—C21 | 113.36 (12) |
N1A—C1B—H11B | 109.00 | C2—C3—C4 | 122.17 (13) |
N1A—C1B—H12B | 109.00 | Cl4—C4—C5 | 121.64 (11) |
C2B—C1B—H12B | 109.00 | C3—C4—C5 | 119.31 (13) |
H11B—C1B—H12B | 108.00 | Cl4—C4—C3 | 119.05 (11) |
C2B—C1B—H11B | 109.00 | Cl5—C5—C6 | 118.86 (11) |
N1A—C1C—H11C | 109.00 | C4—C5—C6 | 119.41 (13) |
N1A—C1C—H12C | 109.00 | Cl5—C5—C4 | 121.73 (11) |
C2C—C1C—H12C | 109.00 | C1—C6—C5 | 122.34 (13) |
H11C—C1C—H12C | 108.00 | O11—C11—C1 | 118.99 (12) |
C2C—C1C—H11C | 109.00 | O12—C11—C1 | 119.52 (12) |
C1A—C2A—H22A | 110.00 | O11—C11—O12 | 121.48 (13) |
C1A—C2A—H23A | 109.00 | O21—C21—C2 | 120.07 (12) |
H21A—C2A—H22A | 109.00 | O22—C21—C2 | 117.45 (12) |
H21A—C2A—H23A | 109.00 | O21—C21—O22 | 122.46 (13) |
H22A—C2A—H23A | 109.00 | C2—C3—H3 | 119.00 |
C1A—C2A—H21A | 109.00 | C4—C3—H3 | 119.00 |
C1B—C2B—H21B | 109.00 | C1—C6—H6 | 119.00 |
C1B—C2B—H23B | 109.00 | C5—C6—H6 | 119.00 |
H21B—C2B—H22B | 109.00 | ||
C1B—N1A—C1A—C2A | −63.19 (16) | C6—C1—C11—O12 | −178.56 (12) |
C1C—N1A—C1A—C2A | 168.20 (12) | C1—C2—C3—C4 | −2.12 (19) |
C1A—N1A—C1B—C2B | −69.93 (15) | C21—C2—C3—C4 | 175.95 (12) |
C1C—N1A—C1B—C2B | 56.65 (16) | C1—C2—C21—O21 | −0.1 (2) |
C1A—N1A—C1C—C2C | −175.17 (13) | C1—C2—C21—O22 | 178.46 (13) |
C1B—N1A—C1C—C2C | 55.98 (16) | C3—C2—C21—O21 | −177.98 (12) |
C6—C1—C2—C3 | 2.37 (18) | C3—C2—C21—O22 | 0.62 (17) |
C6—C1—C2—C21 | −175.38 (12) | C2—C3—C4—Cl4 | −179.47 (10) |
C11—C1—C2—C3 | −176.80 (12) | C2—C3—C4—C5 | 0.12 (19) |
C11—C1—C2—C21 | 5.5 (2) | Cl4—C4—C5—Cl5 | 0.45 (17) |
C2—C1—C6—C5 | −0.73 (19) | Cl4—C4—C5—C6 | −178.84 (10) |
C11—C1—C6—C5 | 178.57 (12) | C3—C4—C5—Cl5 | −179.14 (10) |
C2—C1—C11—O11 | 179.64 (13) | C3—C4—C5—C6 | 1.6 (2) |
C2—C1—C11—O12 | 0.7 (2) | Cl5—C5—C6—C1 | 179.42 (10) |
C6—C1—C11—O11 | 0.44 (18) | C4—C5—C6—C1 | −1.3 (2) |
D—H···A | D—H | H···A | D···A | D—H···A |
N1A—H1A···O21 | 0.910 (15) | 2.569 (16) | 3.1614 (15) | 123.3 (12) |
N1A—H1A···O22 | 0.910 (15) | 1.837 (15) | 2.7433 (16) | 173.7 (14) |
O12—H12···O21 | 0.99 (2) | 1.44 (2) | 2.4223 (14) | 175 (2) |
C3—H3···O22 | 0.95 | 2.29 | 2.6714 (16) | 103 |
C6—H6···O11 | 0.95 | 2.27 | 2.6602 (17) | 104 |
C4H12N+·C8H3Cl2O4− | F(000) = 640 |
Mr = 308.14 | Dx = 1.392 Mg m−3 |
Monoclinic, P21/c | Melting point: 443 K |
Hall symbol: -P 2ybc | Mo Kα radiation, λ = 0.71073 Å |
a = 8.9588 (13) Å | Cell parameters from 2315 reflections |
b = 9.9042 (11) Å | θ = 2.9–32.4° |
c = 17.062 (3) Å | µ = 0.45 mm−1 |
β = 104.580 (14)° | T = 200 K |
V = 1465.2 (3) Å3 | Plate, colourless |
Z = 4 | 0.35 × 0.35 × 0.15 mm |
Oxford Diffraction Gemini-S CCD-detector diffractometer | 2802 independent reflections |
Radiation source: Enhance (Mo) X-ray source | 2159 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.022 |
ω scans | θmax = 26.0°, θmin = 3.0° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −11→10 |
Tmin = 0.926, Tmax = 0.980 | k = −12→7 |
5638 measured reflections | l = −18→21 |
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)] = 0.037 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.106 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.05 | w = 1/[σ2(Fo2) + (0.0641P)2 + 0.1213P] where P = (Fo2 + 2Fc2)/3 |
2802 reflections | (Δ/σ)max = 0.002 |
184 parameters | Δρmax = 0.38 e Å−3 |
0 restraints | Δρmin = −0.26 e Å−3 |
Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su'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 | ||
Cl4 | 0.43514 (6) | −0.20944 (6) | 0.30016 (3) | 0.0438 (2) | |
Cl5 | 0.45031 (7) | −0.32604 (6) | 0.47681 (4) | 0.0495 (2) | |
O11 | 0.82585 (18) | −0.02229 (15) | 0.66675 (8) | 0.0437 (5) | |
O12 | 0.9418 (2) | 0.12902 (18) | 0.60850 (10) | 0.0531 (6) | |
O21 | 0.92748 (19) | 0.21909 (18) | 0.47700 (9) | 0.0508 (6) | |
O22 | 0.7828 (2) | 0.20048 (17) | 0.35291 (9) | 0.0552 (6) | |
C1 | 0.7437 (2) | −0.01323 (18) | 0.52381 (11) | 0.0274 (5) | |
C2 | 0.7347 (2) | 0.04067 (19) | 0.44596 (11) | 0.0280 (6) | |
C3 | 0.6346 (2) | −0.0214 (2) | 0.37922 (11) | 0.0313 (6) | |
C4 | 0.5489 (2) | −0.1348 (2) | 0.38645 (11) | 0.0308 (6) | |
C5 | 0.5570 (2) | −0.18594 (19) | 0.46316 (12) | 0.0310 (6) | |
C6 | 0.6516 (2) | −0.12484 (19) | 0.52986 (11) | 0.0290 (6) | |
C11 | 0.8434 (2) | 0.0344 (2) | 0.60563 (11) | 0.0330 (6) | |
C21 | 0.8196 (2) | 0.1619 (2) | 0.42353 (12) | 0.0362 (7) | |
N1A | 0.9508 (2) | 0.41802 (18) | 0.32003 (10) | 0.0332 (5) | |
C1A | 1.1027 (3) | 0.3524 (3) | 0.32661 (17) | 0.0586 (9) | |
C1B | 0.9510 (3) | 0.5322 (2) | 0.37563 (14) | 0.0499 (8) | |
C2A | 1.2148 (3) | 0.4385 (4) | 0.30110 (18) | 0.0765 (13) | |
C2B | 0.7912 (4) | 0.5749 (4) | 0.3736 (2) | 0.0921 (14) | |
H3 | 0.62520 | 0.01590 | 0.32690 | 0.0380* | |
H6 | 0.65440 | −0.15980 | 0.58210 | 0.0350* | |
H12 | 0.936 (4) | 0.167 (3) | 0.554 (2) | 0.086* | |
H1A | 0.914 (2) | 0.442 (2) | 0.2684 (14) | 0.038 (6)* | |
H2A | 0.888 (3) | 0.349 (3) | 0.3314 (16) | 0.060 (8)* | |
H11A | 1.14620 | 0.32490 | 0.38360 | 0.0700* | |
H11B | 1.00780 | 0.60910 | 0.35990 | 0.0600* | |
H12A | 1.08660 | 0.26960 | 0.29310 | 0.0700* | |
H12B | 1.00490 | 0.50510 | 0.43140 | 0.0600* | |
H21A | 1.23180 | 0.52080 | 0.33400 | 0.0920* | |
H21B | 0.71830 | 0.50620 | 0.34570 | 0.1110* | |
H22A | 1.17520 | 0.46240 | 0.24390 | 0.0920* | |
H22B | 0.76880 | 0.66100 | 0.34480 | 0.1110* | |
H23A | 1.31250 | 0.38970 | 0.30840 | 0.0920* | |
H23B | 0.78090 | 0.58570 | 0.42910 | 0.1110* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Cl4 | 0.0422 (3) | 0.0457 (3) | 0.0369 (3) | 0.0000 (2) | −0.0024 (2) | −0.0119 (2) |
Cl5 | 0.0572 (4) | 0.0336 (3) | 0.0569 (4) | −0.0110 (2) | 0.0127 (3) | 0.0009 (2) |
O11 | 0.0622 (10) | 0.0417 (9) | 0.0237 (7) | −0.0002 (7) | 0.0043 (6) | 0.0001 (6) |
O12 | 0.0602 (11) | 0.0574 (10) | 0.0333 (8) | −0.0215 (9) | −0.0041 (7) | 0.0010 (8) |
O21 | 0.0511 (10) | 0.0562 (10) | 0.0402 (9) | −0.0220 (8) | 0.0023 (7) | 0.0072 (8) |
O22 | 0.0672 (11) | 0.0540 (10) | 0.0379 (9) | −0.0187 (9) | 0.0010 (8) | 0.0165 (8) |
C1 | 0.0282 (10) | 0.0272 (9) | 0.0255 (9) | 0.0089 (8) | 0.0046 (7) | −0.0012 (8) |
C2 | 0.0271 (10) | 0.0297 (10) | 0.0273 (9) | 0.0063 (8) | 0.0068 (8) | 0.0024 (8) |
C3 | 0.0327 (11) | 0.0362 (11) | 0.0242 (9) | 0.0060 (8) | 0.0057 (8) | 0.0011 (8) |
C4 | 0.0287 (10) | 0.0307 (10) | 0.0306 (10) | 0.0044 (8) | 0.0028 (8) | −0.0057 (8) |
C5 | 0.0298 (10) | 0.0244 (10) | 0.0390 (11) | 0.0050 (8) | 0.0093 (8) | −0.0014 (8) |
C6 | 0.0337 (11) | 0.0269 (10) | 0.0267 (10) | 0.0075 (8) | 0.0080 (8) | 0.0033 (8) |
C11 | 0.0381 (11) | 0.0310 (10) | 0.0267 (10) | 0.0080 (9) | 0.0023 (8) | −0.0018 (8) |
C21 | 0.0354 (12) | 0.0384 (11) | 0.0341 (11) | −0.0002 (9) | 0.0076 (9) | 0.0033 (9) |
N1A | 0.0431 (10) | 0.0321 (9) | 0.0248 (9) | 0.0045 (8) | 0.0093 (7) | 0.0043 (7) |
C1A | 0.0611 (17) | 0.0593 (16) | 0.0605 (16) | 0.0212 (13) | 0.0251 (13) | 0.0154 (13) |
C1B | 0.0694 (17) | 0.0424 (13) | 0.0364 (12) | 0.0043 (12) | 0.0105 (11) | −0.0094 (10) |
C2A | 0.0464 (16) | 0.119 (3) | 0.0653 (18) | 0.0012 (17) | 0.0161 (13) | 0.0123 (18) |
C2B | 0.091 (2) | 0.093 (3) | 0.097 (2) | 0.037 (2) | 0.0325 (19) | −0.021 (2) |
Cl4—C4 | 1.731 (2) | C4—C5 | 1.388 (3) |
Cl5—C5 | 1.734 (2) | C5—C6 | 1.376 (3) |
O11—C11 | 1.229 (2) | C3—H3 | 0.9500 |
O12—C11 | 1.279 (3) | C6—H6 | 0.9500 |
O21—C21 | 1.282 (3) | C1A—C2A | 1.465 (4) |
O22—C21 | 1.227 (2) | C1B—C2B | 1.485 (5) |
O12—H12 | 0.99 (3) | C1A—H11A | 0.9900 |
N1A—C1B | 1.476 (3) | C1A—H12A | 0.9900 |
N1A—C1A | 1.487 (3) | C1B—H11B | 0.9900 |
N1A—H2A | 0.94 (3) | C1B—H12B | 0.9900 |
N1A—H1A | 0.89 (2) | C2A—H21A | 0.9800 |
C1—C6 | 1.399 (3) | C2A—H22A | 0.9800 |
C1—C2 | 1.415 (3) | C2A—H23A | 0.9800 |
C1—C11 | 1.530 (3) | C2B—H21B | 0.9800 |
C2—C21 | 1.521 (3) | C2B—H22B | 0.9800 |
C2—C3 | 1.402 (3) | C2B—H23B | 0.9800 |
C3—C4 | 1.383 (3) | ||
C11—O12—H12 | 111.7 (19) | C4—C3—H3 | 119.00 |
C1A—N1A—C1B | 115.69 (19) | C1—C6—H6 | 119.00 |
C1B—N1A—H1A | 111.8 (13) | C5—C6—H6 | 119.00 |
C1B—N1A—H2A | 109.3 (17) | N1A—C1A—C2A | 114.0 (2) |
H1A—N1A—H2A | 108 (2) | N1A—C1B—C2B | 111.0 (2) |
C1A—N1A—H1A | 107.2 (13) | N1A—C1A—H11A | 109.00 |
C1A—N1A—H2A | 104.6 (18) | N1A—C1A—H12A | 109.00 |
C6—C1—C11 | 113.33 (16) | C2A—C1A—H11A | 109.00 |
C2—C1—C6 | 118.18 (17) | C2A—C1A—H12A | 109.00 |
C2—C1—C11 | 128.49 (16) | H11A—C1A—H12A | 108.00 |
C1—C2—C21 | 128.33 (17) | N1A—C1B—H11B | 109.00 |
C1—C2—C3 | 118.09 (17) | N1A—C1B—H12B | 109.00 |
C3—C2—C21 | 113.58 (16) | C2B—C1B—H11B | 109.00 |
C2—C3—C4 | 122.65 (17) | C2B—C1B—H12B | 110.00 |
Cl4—C4—C5 | 121.73 (15) | H11B—C1B—H12B | 108.00 |
C3—C4—C5 | 118.81 (17) | C1A—C2A—H21A | 109.00 |
Cl4—C4—C3 | 119.47 (14) | C1A—C2A—H22A | 109.00 |
Cl5—C5—C4 | 121.26 (15) | C1A—C2A—H23A | 109.00 |
Cl5—C5—C6 | 119.11 (15) | H21A—C2A—H22A | 110.00 |
C4—C5—C6 | 119.63 (17) | H21A—C2A—H23A | 109.00 |
C1—C6—C5 | 122.58 (17) | H22A—C2A—H23A | 109.00 |
O11—C11—O12 | 122.44 (18) | C1B—C2B—H21B | 110.00 |
O11—C11—C1 | 117.61 (17) | C1B—C2B—H22B | 110.00 |
O12—C11—C1 | 119.95 (17) | C1B—C2B—H23B | 109.00 |
O21—C21—O22 | 121.95 (19) | H21B—C2B—H22B | 109.00 |
O22—C21—C2 | 117.71 (18) | H21B—C2B—H23B | 109.00 |
O21—C21—C2 | 120.33 (17) | H22B—C2B—H23B | 109.00 |
C2—C3—H3 | 119.00 | ||
C1A—N1A—C1B—C2B | −170.6 (2) | C1—C2—C21—O22 | −172.41 (19) |
C1B—N1A—C1A—C2A | −67.1 (3) | C21—C2—C3—C4 | 178.72 (17) |
C6—C1—C2—C21 | 178.71 (18) | C3—C2—C21—O22 | 6.7 (3) |
C6—C1—C2—C3 | −0.4 (3) | C3—C2—C21—O21 | −172.07 (18) |
C2—C1—C6—C5 | 2.0 (3) | C1—C2—C3—C4 | −2.1 (3) |
C11—C1—C6—C5 | −177.95 (17) | C2—C3—C4—Cl4 | −176.95 (15) |
C2—C1—C11—O11 | 175.50 (19) | C2—C3—C4—C5 | 2.9 (3) |
C2—C1—C11—O12 | −5.3 (3) | Cl4—C4—C5—C6 | 178.62 (15) |
C6—C1—C11—O11 | −4.6 (3) | C3—C4—C5—Cl5 | 178.93 (15) |
C11—C1—C2—C3 | 179.57 (18) | Cl4—C4—C5—Cl5 | −1.2 (2) |
C11—C1—C2—C21 | −1.3 (3) | C3—C4—C5—C6 | −1.2 (3) |
C6—C1—C11—O12 | 174.69 (18) | C4—C5—C6—C1 | −1.2 (3) |
C1—C2—C21—O21 | 8.8 (3) | Cl5—C5—C6—C1 | 178.64 (15) |
D—H···A | D—H | H···A | D···A | D—H···A |
N1A—H1A···O11i | 0.89 (2) | 1.89 (2) | 2.772 (2) | 169.6 (19) |
N1A—H2A···O22 | 0.94 (3) | 1.83 (3) | 2.765 (3) | 173 (3) |
O12—H12···O21 | 0.99 (3) | 1.40 (3) | 2.388 (2) | 179 (4) |
C3—H3···O22 | 0.95 | 2.28 | 2.663 (3) | 103 |
C6—H6···O11 | 0.95 | 2.28 | 2.662 (2) | 103 |
Symmetry code: (i) x, −y+1/2, z−1/2. |
2C4H12N+·C8H2Cl2O42−·H2O | Z = 2 |
Mr = 399.30 | F(000) = 424 |
Triclinic, P1 | Dx = 1.253 Mg m−3 |
Hall symbol: -P 1 | Melting point: 457 K |
a = 8.1362 (6) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 9.3043 (11) Å | Cell parameters from 6406 reflections |
c = 15.406 (1) Å | θ = 3.0–32.5° |
α = 78.678 (7)° | µ = 0.33 mm−1 |
β = 85.846 (6)° | T = 200 K |
γ = 67.777 (9)° | Prism, colourless |
V = 1058.62 (18) Å3 | 0.55 × 0.30 × 0.20 mm |
Oxford Diffraction Gemini-S CCD-detector diffractometer | 4851 independent reflections |
Radiation source: Enhance (Mo) X-ray source | 3858 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.041 |
Detector resolution: 16.077 pixels mm-1 | θmax = 27.5°, θmin = 3.0° |
ω scans | h = −10→10 |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | k = −12→12 |
Tmin = 0.865, Tmax = 0.940 | l = −19→19 |
15869 measured reflections |
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)] = 0.046 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.145 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.18 | w = 1/[σ2(Fo2) + (0.0837P)2 + 0.0287P] where P = (Fo2 + 2Fc2)/3 |
4851 reflections | (Δ/σ)max = 0.001 |
260 parameters | Δρmax = 0.41 e Å−3 |
0 restraints | Δρmin = −0.29 e Å−3 |
Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su'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 | ||
N1A | 0.83030 (18) | 0.40803 (16) | 0.43961 (9) | 0.0301 (4) | |
C2A | 0.8506 (2) | 0.53396 (18) | 0.36814 (11) | 0.0363 (5) | |
C3A | 0.8949 (3) | 0.4766 (2) | 0.28024 (13) | 0.0498 (6) | |
C4A | 0.8915 (3) | 0.6078 (3) | 0.20387 (16) | 0.0660 (8) | |
C5A | 0.7110 (4) | 0.7306 (3) | 0.18164 (17) | 0.0741 (9) | |
N1B | 0.32948 (19) | −0.11939 (16) | 0.40526 (10) | 0.0331 (4) | |
C2B | 0.1554 (2) | −0.0456 (2) | 0.35886 (13) | 0.0438 (6) | |
C3B | 0.1793 (2) | −0.0228 (2) | 0.25901 (13) | 0.0482 (6) | |
C4B | 0.0032 (3) | 0.0372 (3) | 0.21012 (16) | 0.0626 (8) | |
C5B | 0.0245 (5) | 0.0527 (5) | 0.1113 (2) | 0.1087 (13) | |
Cl4 | 0.46735 (10) | 0.17647 (7) | 0.03754 (3) | 0.0717 (2) | |
Cl5 | 0.26463 (8) | 0.54775 (7) | 0.02437 (3) | 0.0627 (2) | |
O11 | 0.45042 (17) | 0.59391 (14) | 0.35104 (9) | 0.0444 (4) | |
O12 | 0.31110 (18) | 0.43995 (16) | 0.41980 (9) | 0.0493 (5) | |
O21 | 0.68790 (15) | 0.18640 (13) | 0.41153 (7) | 0.0364 (4) | |
O22 | 0.61194 (15) | −0.00555 (12) | 0.38236 (8) | 0.0351 (3) | |
C1 | 0.42808 (18) | 0.40301 (16) | 0.27681 (10) | 0.0254 (4) | |
C2 | 0.51625 (18) | 0.23900 (16) | 0.28276 (10) | 0.0257 (4) | |
C3 | 0.5259 (2) | 0.17325 (18) | 0.20775 (11) | 0.0340 (5) | |
C4 | 0.4510 (2) | 0.2661 (2) | 0.12824 (11) | 0.0405 (5) | |
C5 | 0.3648 (2) | 0.4280 (2) | 0.12225 (11) | 0.0392 (5) | |
C6 | 0.3565 (2) | 0.49536 (18) | 0.19618 (11) | 0.0330 (5) | |
C11 | 0.39599 (18) | 0.48459 (16) | 0.35637 (10) | 0.0270 (4) | |
C21 | 0.61058 (18) | 0.13221 (16) | 0.36576 (10) | 0.0256 (4) | |
O1W | 0.18354 (16) | 0.20557 (14) | 0.47498 (9) | 0.0410 (4) | |
H11A | 0.781 (3) | 0.447 (2) | 0.4846 (15) | 0.048 (6)* | |
H12A | 0.936 (3) | 0.329 (2) | 0.4554 (12) | 0.035 (5)* | |
H13A | 0.763 (3) | 0.357 (2) | 0.4210 (13) | 0.041 (5)* | |
H21A | 0.94650 | 0.56500 | 0.38430 | 0.0430* | |
H22A | 0.73900 | 0.62810 | 0.36210 | 0.0430* | |
H31A | 1.01440 | 0.39180 | 0.28420 | 0.0600* | |
H32A | 0.80840 | 0.43120 | 0.26860 | 0.0600* | |
H41A | 0.96950 | 0.65950 | 0.21850 | 0.0790* | |
H42A | 0.94130 | 0.56080 | 0.15090 | 0.0790* | |
H51A | 0.71990 | 0.81250 | 0.13290 | 0.0890* | |
H52A | 0.66030 | 0.77810 | 0.23360 | 0.0890* | |
H53A | 0.63420 | 0.68170 | 0.16390 | 0.0890* | |
H11B | 0.398 (3) | −0.064 (2) | 0.3886 (14) | 0.046 (5)* | |
H12B | 0.315 (3) | −0.126 (2) | 0.4632 (17) | 0.049 (6)* | |
H13B | 0.380 (3) | −0.216 (3) | 0.3920 (13) | 0.043 (5)* | |
H21B | 0.08830 | 0.05800 | 0.37610 | 0.0530* | |
H22B | 0.08560 | −0.11360 | 0.37710 | 0.0530* | |
H31B | 0.25720 | −0.12460 | 0.24260 | 0.0580* | |
H32B | 0.23870 | 0.05360 | 0.24040 | 0.0580* | |
H41B | −0.05890 | −0.03630 | 0.23140 | 0.0750* | |
H42B | −0.07200 | 0.14150 | 0.22440 | 0.0750* | |
H51B | −0.09080 | 0.07900 | 0.08400 | 0.1300* | |
H52B | 0.10830 | −0.04750 | 0.09690 | 0.1300* | |
H53B | 0.06990 | 0.13660 | 0.08860 | 0.1300* | |
H3 | 0.58500 | 0.06250 | 0.21130 | 0.0410* | |
H6 | 0.30080 | 0.60660 | 0.19140 | 0.0400* | |
H11W | 0.233 (3) | 0.276 (3) | 0.4557 (14) | 0.051 (6)* | |
H12W | 0.242 (4) | 0.153 (3) | 0.5268 (19) | 0.078 (8)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
N1A | 0.0276 (7) | 0.0331 (7) | 0.0318 (7) | −0.0118 (6) | −0.0005 (5) | −0.0098 (5) |
C2A | 0.0328 (8) | 0.0327 (8) | 0.0402 (9) | −0.0102 (6) | 0.0000 (7) | −0.0037 (6) |
C3A | 0.0480 (11) | 0.0480 (10) | 0.0435 (11) | −0.0085 (8) | 0.0091 (8) | −0.0083 (8) |
C4A | 0.0640 (14) | 0.0732 (15) | 0.0523 (14) | −0.0219 (12) | 0.0087 (11) | −0.0025 (11) |
C5A | 0.0809 (17) | 0.0767 (16) | 0.0498 (14) | −0.0204 (13) | −0.0099 (12) | 0.0075 (11) |
N1B | 0.0381 (7) | 0.0303 (7) | 0.0348 (8) | −0.0149 (6) | −0.0019 (6) | −0.0100 (6) |
C2B | 0.0365 (9) | 0.0495 (10) | 0.0476 (11) | −0.0122 (8) | −0.0053 (8) | −0.0199 (8) |
C3B | 0.0392 (10) | 0.0500 (10) | 0.0496 (12) | −0.0116 (8) | −0.0055 (8) | −0.0039 (8) |
C4B | 0.0576 (13) | 0.0642 (13) | 0.0617 (14) | −0.0125 (11) | −0.0184 (10) | −0.0160 (10) |
C5B | 0.091 (2) | 0.148 (3) | 0.0578 (18) | −0.014 (2) | −0.0309 (16) | −0.0031 (18) |
Cl4 | 0.1103 (5) | 0.0770 (4) | 0.0354 (3) | −0.0340 (4) | −0.0094 (3) | −0.0258 (2) |
Cl5 | 0.0678 (4) | 0.0743 (4) | 0.0323 (3) | −0.0172 (3) | −0.0134 (2) | 0.0077 (2) |
O11 | 0.0576 (8) | 0.0330 (6) | 0.0521 (8) | −0.0238 (6) | 0.0047 (6) | −0.0168 (5) |
O12 | 0.0630 (8) | 0.0618 (8) | 0.0433 (8) | −0.0404 (7) | 0.0230 (6) | −0.0288 (6) |
O21 | 0.0452 (7) | 0.0362 (6) | 0.0348 (6) | −0.0223 (5) | −0.0114 (5) | −0.0037 (4) |
O22 | 0.0389 (6) | 0.0251 (5) | 0.0421 (7) | −0.0125 (5) | −0.0086 (5) | −0.0037 (4) |
C1 | 0.0215 (6) | 0.0275 (7) | 0.0290 (8) | −0.0106 (5) | 0.0006 (5) | −0.0067 (5) |
C2 | 0.0248 (7) | 0.0274 (7) | 0.0287 (8) | −0.0126 (6) | 0.0006 (5) | −0.0080 (5) |
C3 | 0.0403 (9) | 0.0336 (8) | 0.0327 (9) | −0.0158 (7) | 0.0007 (7) | −0.0128 (6) |
C4 | 0.0491 (10) | 0.0510 (10) | 0.0273 (8) | −0.0221 (8) | −0.0011 (7) | −0.0130 (7) |
C5 | 0.0398 (9) | 0.0482 (10) | 0.0282 (9) | −0.0171 (7) | −0.0040 (7) | −0.0007 (7) |
C6 | 0.0305 (8) | 0.0321 (8) | 0.0347 (9) | −0.0118 (6) | 0.0009 (6) | −0.0024 (6) |
C11 | 0.0218 (6) | 0.0241 (7) | 0.0335 (8) | −0.0051 (5) | −0.0022 (6) | −0.0080 (5) |
C21 | 0.0229 (7) | 0.0258 (7) | 0.0292 (8) | −0.0085 (5) | 0.0017 (5) | −0.0096 (5) |
O1W | 0.0353 (6) | 0.0332 (6) | 0.0526 (8) | −0.0114 (5) | −0.0122 (6) | −0.0019 (5) |
Cl4—C4 | 1.7356 (18) | C5A—H51A | 0.9800 |
Cl5—C5 | 1.7352 (18) | C5A—H52A | 0.9800 |
O11—C11 | 1.241 (2) | C5A—H53A | 0.9800 |
O12—C11 | 1.251 (2) | C2B—C3B | 1.520 (3) |
O21—C21 | 1.2613 (19) | C3B—C4B | 1.523 (3) |
O22—C21 | 1.2528 (18) | C4B—C5B | 1.504 (4) |
O1W—H11W | 0.89 (3) | C2B—H22B | 0.9900 |
O1W—H12W | 0.91 (3) | C2B—H21B | 0.9900 |
N1A—C2A | 1.492 (2) | C3B—H32B | 0.9900 |
N1A—H13A | 0.94 (2) | C3B—H31B | 0.9900 |
N1A—H12A | 0.91 (2) | C4B—H42B | 0.9900 |
N1A—H11A | 0.85 (2) | C4B—H41B | 0.9900 |
N1B—C2B | 1.486 (2) | C5B—H53B | 0.9800 |
N1B—H12B | 0.89 (3) | C5B—H52B | 0.9800 |
N1B—H13B | 0.89 (3) | C5B—H51B | 0.9800 |
N1B—H11B | 0.89 (2) | C1—C11 | 1.522 (2) |
C2A—C3A | 1.522 (3) | C1—C2 | 1.407 (2) |
C3A—C4A | 1.513 (3) | C1—C6 | 1.388 (2) |
C4A—C5A | 1.493 (4) | C2—C21 | 1.509 (2) |
C2A—H21A | 0.9900 | C2—C3 | 1.394 (2) |
C2A—H22A | 0.9900 | C3—C4 | 1.383 (2) |
C3A—H32A | 0.9900 | C4—C5 | 1.388 (2) |
C3A—H31A | 0.9900 | C5—C6 | 1.390 (2) |
C4A—H42A | 0.9900 | C3—H3 | 0.9500 |
C4A—H41A | 0.9900 | C6—H6 | 0.9500 |
H11W—O1W—H12W | 103 (2) | H21B—C2B—H22B | 108.00 |
H12A—N1A—H13A | 103.8 (18) | N1B—C2B—H21B | 109.00 |
C2A—N1A—H13A | 112.1 (12) | C2B—C3B—H31B | 109.00 |
H11A—N1A—H13A | 109 (2) | C2B—C3B—H32B | 109.00 |
C2A—N1A—H12A | 111.8 (13) | C4B—C3B—H32B | 109.00 |
C2A—N1A—H11A | 110.2 (13) | H31B—C3B—H32B | 108.00 |
H11A—N1A—H12A | 109.8 (19) | C4B—C3B—H31B | 109.00 |
C2B—N1B—H11B | 112.0 (14) | C3B—C4B—H41B | 109.00 |
H11B—N1B—H13B | 111 (2) | C5B—C4B—H41B | 109.00 |
H12B—N1B—H13B | 110.1 (17) | C5B—C4B—H42B | 109.00 |
C2B—N1B—H13B | 106.0 (16) | C3B—C4B—H42B | 109.00 |
C2B—N1B—H12B | 110.8 (16) | H41B—C4B—H42B | 108.00 |
H11B—N1B—H12B | 107 (2) | C4B—C5B—H52B | 109.00 |
N1A—C2A—C3A | 110.92 (13) | C4B—C5B—H53B | 109.00 |
C2A—C3A—C4A | 112.32 (16) | H51B—C5B—H52B | 109.00 |
C3A—C4A—C5A | 114.3 (2) | H51B—C5B—H53B | 109.00 |
N1A—C2A—H22A | 109.00 | H52B—C5B—H53B | 109.00 |
H21A—C2A—H22A | 108.00 | C4B—C5B—H51B | 109.00 |
C3A—C2A—H21A | 109.00 | C2—C1—C6 | 119.26 (14) |
N1A—C2A—H21A | 109.00 | C2—C1—C11 | 123.08 (13) |
C3A—C2A—H22A | 109.00 | C6—C1—C11 | 117.54 (13) |
C4A—C3A—H32A | 109.00 | C1—C2—C21 | 122.55 (13) |
C2A—C3A—H31A | 109.00 | C3—C2—C21 | 118.43 (13) |
C4A—C3A—H31A | 109.00 | C1—C2—C3 | 118.92 (14) |
H31A—C3A—H32A | 108.00 | C2—C3—C4 | 121.28 (15) |
C2A—C3A—H32A | 109.00 | Cl4—C4—C3 | 118.88 (13) |
H41A—C4A—H42A | 108.00 | Cl4—C4—C5 | 121.31 (13) |
C5A—C4A—H41A | 109.00 | C3—C4—C5 | 119.81 (15) |
C3A—C4A—H41A | 109.00 | Cl5—C5—C6 | 119.35 (13) |
C3A—C4A—H42A | 109.00 | C4—C5—C6 | 119.50 (15) |
C5A—C4A—H42A | 109.00 | Cl5—C5—C4 | 121.14 (13) |
C4A—C5A—H51A | 109.00 | C1—C6—C5 | 121.20 (15) |
C4A—C5A—H52A | 109.00 | O11—C11—C1 | 116.95 (14) |
C4A—C5A—H53A | 109.00 | O12—C11—C1 | 117.25 (14) |
H51A—C5A—H52A | 109.00 | O11—C11—O12 | 125.74 (15) |
H51A—C5A—H53A | 110.00 | O21—C21—C2 | 117.53 (13) |
H52A—C5A—H53A | 109.00 | O22—C21—C2 | 117.62 (14) |
N1B—C2B—C3B | 111.23 (15) | O21—C21—O22 | 124.80 (14) |
C2B—C3B—C4B | 112.19 (16) | C2—C3—H3 | 119.00 |
C3B—C4B—C5B | 113.1 (2) | C4—C3—H3 | 119.00 |
N1B—C2B—H22B | 109.00 | C1—C6—H6 | 119.00 |
C3B—C2B—H21B | 109.00 | C5—C6—H6 | 119.00 |
C3B—C2B—H22B | 109.00 | ||
N1A—C2A—C3A—C4A | 172.11 (18) | C1—C2—C3—C4 | 0.1 (3) |
C2A—C3A—C4A—C5A | −68.3 (3) | C21—C2—C3—C4 | −176.29 (15) |
N1B—C2B—C3B—C4B | 174.22 (16) | C1—C2—C21—O21 | −35.3 (2) |
C2B—C3B—C4B—C5B | −177.1 (2) | C1—C2—C21—O22 | 147.30 (15) |
C6—C1—C2—C3 | −1.4 (2) | C3—C2—C21—O21 | 140.96 (16) |
C6—C1—C2—C21 | 174.86 (15) | C3—C2—C21—O22 | −36.4 (2) |
C11—C1—C2—C3 | 174.49 (15) | C2—C3—C4—Cl4 | −179.82 (14) |
C11—C1—C2—C21 | −9.3 (2) | C2—C3—C4—C5 | 0.2 (3) |
C2—C1—C6—C5 | 2.4 (3) | Cl4—C4—C5—Cl5 | 1.6 (2) |
C11—C1—C6—C5 | −173.73 (15) | Cl4—C4—C5—C6 | −179.23 (14) |
C2—C1—C11—O11 | 125.03 (17) | C3—C4—C5—Cl5 | −178.45 (14) |
C2—C1—C11—O12 | −57.7 (2) | C3—C4—C5—C6 | 0.7 (3) |
C6—C1—C11—O11 | −59.0 (2) | Cl5—C5—C6—C1 | 177.15 (13) |
C6—C1—C11—O12 | 118.20 (17) | C4—C5—C6—C1 | −2.1 (3) |
D—H···A | D—H | H···A | D···A | D—H···A |
N1A—H11A···O12i | 0.85 (2) | 1.92 (2) | 2.762 (2) | 170 (2) |
N1A—H12A···O1Wii | 0.91 (2) | 1.92 (2) | 2.799 (2) | 164 (2) |
N1A—H13A···O21 | 0.94 (2) | 1.94 (2) | 2.831 (2) | 158.4 (17) |
N1B—H11B···O22 | 0.89 (2) | 2.00 (3) | 2.847 (2) | 158.9 (19) |
N1B—H12B···O21iii | 0.89 (3) | 1.90 (3) | 2.7737 (19) | 167.9 (17) |
N1B—H13B···O11iv | 0.89 (3) | 1.86 (3) | 2.7481 (19) | 170 (2) |
O1W—H11W···O12 | 0.89 (3) | 1.84 (3) | 2.723 (2) | 173 (2) |
O1W—H12W···O22iii | 0.91 (3) | 1.87 (3) | 2.7648 (18) | 166 (3) |
C2B—H21B···O1W | 0.99 | 2.57 | 3.289 (2) | 130 |
C2A—H22A···O11 | 0.99 | 2.51 | 3.110 (2) | 119 |
Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) x+1, y, z; (iii) −x+1, −y, −z+1; (iv) x, y−1, z. |
2C5H12N+·C8H2Cl2O42−·H2O | F(000) = 896 |
Mr = 423.32 | Dx = 1.332 Mg m−3 |
Monoclinic, P21/c | Melting point: 405 K |
Hall symbol: -P 2ybc | Mo Kα radiation, λ = 0.71073 Å |
a = 13.8481 (10) Å | Cell parameters from 6842 reflections |
b = 10.5937 (8) Å | θ = 3.4–28.8° |
c = 14.6129 (10) Å | µ = 0.34 mm−1 |
β = 99.903 (7)° | T = 200 K |
V = 2111.8 (3) Å3 | Plate, colourless |
Z = 4 | 0.35 × 0.20 × 0.18 mm |
Oxford Diffraction Gemini-S CCD-detector diffractometer | 4805 independent reflections |
Radiation source: Enhance (Mo) X-ray source | 3570 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.057 |
Detector resolution: 16.077 pixels mm-1 | θmax = 27.5°, θmin = 3.4° |
ω scans | h = −17→17 |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | k = −13→13 |
Tmin = 0.701, Tmax = 0.980 | l = −18→18 |
26626 measured reflections |
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)] = 0.038 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.103 | H atoms treated by a mixture of independent and constrained refinement |
S = 0.96 | w = 1/[σ2(Fo2) + (0.0644P)2] where P = (Fo2 + 2Fc2)/3 |
4805 reflections | (Δ/σ)max < 0.001 |
268 parameters | Δρmax = 0.26 e Å−3 |
0 restraints | Δρmin = −0.29 e Å−3 |
Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su'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 | ||
N1A | 0.06019 (10) | 0.62705 (12) | 0.30611 (8) | 0.0248 (4) | |
C2A | 0.08561 (12) | 0.59975 (16) | 0.40785 (10) | 0.0342 (5) | |
C3A | 0.19204 (12) | 0.55895 (17) | 0.43278 (11) | 0.0389 (5) | |
C4A | 0.21235 (12) | 0.44461 (15) | 0.37525 (11) | 0.0360 (5) | |
C5A | 0.18615 (12) | 0.47509 (15) | 0.27239 (11) | 0.0345 (5) | |
C6A | 0.07982 (12) | 0.51771 (15) | 0.24770 (11) | 0.0336 (5) | |
N1B | −0.18744 (9) | 0.53788 (12) | 0.07825 (9) | 0.0259 (4) | |
C2B | −0.17157 (12) | 0.47472 (15) | −0.00943 (11) | 0.0331 (5) | |
C3B | −0.25761 (14) | 0.39003 (16) | −0.04612 (12) | 0.0422 (6) | |
C4B | −0.35296 (14) | 0.46454 (18) | −0.06222 (13) | 0.0497 (6) | |
C5B | −0.36718 (13) | 0.53043 (18) | 0.02755 (13) | 0.0450 (6) | |
C6B | −0.27991 (11) | 0.61271 (14) | 0.06581 (11) | 0.0307 (5) | |
Cl4 | 0.54291 (3) | 1.11882 (5) | 0.10952 (4) | 0.0515 (2) | |
Cl5 | 0.54725 (3) | 0.83387 (4) | 0.18411 (4) | 0.0524 (2) | |
O11 | 0.18070 (8) | 0.83778 (9) | 0.29506 (7) | 0.0299 (3) | |
O12 | 0.11586 (8) | 0.85918 (11) | 0.14445 (8) | 0.0389 (4) | |
O21 | 0.13624 (7) | 1.13683 (10) | 0.22891 (7) | 0.0297 (3) | |
O22 | 0.15811 (8) | 1.22425 (10) | 0.09345 (7) | 0.0358 (3) | |
C1 | 0.27323 (10) | 0.94353 (13) | 0.19485 (9) | 0.0210 (4) | |
C2 | 0.27163 (10) | 1.06951 (13) | 0.16393 (9) | 0.0210 (4) | |
C3 | 0.35526 (11) | 1.12116 (14) | 0.13754 (10) | 0.0268 (4) | |
C4 | 0.44021 (11) | 1.05035 (15) | 0.14302 (11) | 0.0305 (4) | |
C5 | 0.44221 (11) | 0.92640 (15) | 0.17569 (11) | 0.0301 (4) | |
C6 | 0.35922 (11) | 0.87368 (14) | 0.20170 (10) | 0.0269 (4) | |
C11 | 0.18131 (10) | 0.87618 (13) | 0.21301 (10) | 0.0232 (4) | |
C21 | 0.18026 (10) | 1.15032 (12) | 0.16064 (10) | 0.0231 (4) | |
O1W | −0.03247 (9) | 0.70087 (11) | 0.06512 (9) | 0.0373 (4) | |
H11A | −0.0042 (15) | 0.6453 (17) | 0.2911 (12) | 0.044 (5)* | |
H12A | 0.0983 (13) | 0.6934 (18) | 0.2940 (12) | 0.047 (5)* | |
H21A | 0.04250 | 0.53200 | 0.42450 | 0.0410* | |
H22A | 0.07470 | 0.67630 | 0.44360 | 0.0410* | |
H31A | 0.20710 | 0.53740 | 0.49960 | 0.0470* | |
H32A | 0.23520 | 0.62960 | 0.42130 | 0.0470* | |
H41A | 0.28250 | 0.42150 | 0.39070 | 0.0430* | |
H42A | 0.17310 | 0.37180 | 0.39020 | 0.0430* | |
H51A | 0.19630 | 0.39930 | 0.23550 | 0.0410* | |
H52A | 0.22980 | 0.54270 | 0.25650 | 0.0410* | |
H61A | 0.06540 | 0.54200 | 0.18130 | 0.0400* | |
H62A | 0.03600 | 0.44680 | 0.25720 | 0.0400* | |
H11B | −0.1854 (13) | 0.4805 (16) | 0.1236 (12) | 0.039 (5)* | |
H12B | −0.1311 (14) | 0.5936 (17) | 0.0945 (12) | 0.044 (5)* | |
H21B | −0.11070 | 0.42400 | 0.00270 | 0.0400* | |
H22B | −0.16390 | 0.53940 | −0.05660 | 0.0400* | |
H31B | −0.26200 | 0.32150 | −0.00100 | 0.0510* | |
H32B | −0.24730 | 0.35100 | −0.10520 | 0.0510* | |
H41B | −0.40870 | 0.40680 | −0.08300 | 0.0600* | |
H42B | −0.35120 | 0.52820 | −0.11150 | 0.0600* | |
H51B | −0.42700 | 0.58320 | 0.01540 | 0.0540* | |
H52B | −0.37650 | 0.46610 | 0.07440 | 0.0540* | |
H61B | −0.27540 | 0.68360 | 0.02260 | 0.0370* | |
H62B | −0.28900 | 0.64860 | 0.12630 | 0.0370* | |
H3 | 0.35400 | 1.20570 | 0.11560 | 0.0320* | |
H6 | 0.36120 | 0.78950 | 0.22430 | 0.0320* | |
H11W | 0.0098 (15) | 0.749 (2) | 0.0907 (14) | 0.058 (6)* | |
H12W | −0.0602 (15) | 0.733 (2) | 0.0152 (15) | 0.062 (7)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
N1A | 0.0213 (6) | 0.0236 (6) | 0.0299 (7) | −0.0011 (5) | 0.0052 (5) | 0.0039 (5) |
C2A | 0.0371 (9) | 0.0404 (9) | 0.0275 (8) | 0.0061 (7) | 0.0125 (7) | 0.0033 (7) |
C3A | 0.0399 (10) | 0.0512 (10) | 0.0245 (8) | 0.0100 (8) | 0.0024 (7) | 0.0046 (7) |
C4A | 0.0330 (9) | 0.0295 (8) | 0.0462 (10) | 0.0073 (7) | 0.0091 (8) | 0.0095 (7) |
C5A | 0.0378 (9) | 0.0297 (8) | 0.0379 (9) | 0.0027 (7) | 0.0117 (7) | −0.0075 (7) |
C6A | 0.0375 (9) | 0.0314 (8) | 0.0307 (8) | −0.0028 (7) | 0.0025 (7) | −0.0055 (7) |
N1B | 0.0287 (7) | 0.0250 (6) | 0.0233 (6) | −0.0024 (5) | 0.0022 (5) | 0.0025 (5) |
C2B | 0.0396 (9) | 0.0299 (8) | 0.0311 (8) | 0.0024 (7) | 0.0102 (7) | −0.0005 (7) |
C3B | 0.0607 (12) | 0.0288 (9) | 0.0369 (9) | −0.0078 (8) | 0.0078 (8) | −0.0084 (7) |
C4B | 0.0457 (11) | 0.0503 (11) | 0.0469 (11) | −0.0139 (9) | −0.0094 (9) | −0.0086 (9) |
C5B | 0.0278 (9) | 0.0525 (11) | 0.0531 (11) | −0.0037 (8) | 0.0021 (8) | −0.0069 (9) |
C6B | 0.0323 (8) | 0.0286 (8) | 0.0302 (8) | 0.0032 (6) | 0.0026 (7) | −0.0034 (6) |
Cl4 | 0.0308 (2) | 0.0537 (3) | 0.0743 (3) | −0.0102 (2) | 0.0215 (2) | 0.0062 (2) |
Cl5 | 0.0289 (2) | 0.0503 (3) | 0.0797 (4) | 0.0127 (2) | 0.0138 (2) | 0.0071 (2) |
O11 | 0.0381 (6) | 0.0253 (5) | 0.0275 (6) | −0.0063 (5) | 0.0090 (5) | 0.0026 (4) |
O12 | 0.0322 (6) | 0.0507 (7) | 0.0315 (6) | −0.0181 (5) | −0.0007 (5) | −0.0057 (5) |
O21 | 0.0250 (5) | 0.0354 (6) | 0.0286 (6) | 0.0035 (4) | 0.0047 (4) | 0.0006 (5) |
O22 | 0.0364 (6) | 0.0337 (6) | 0.0352 (6) | 0.0048 (5) | 0.0001 (5) | 0.0126 (5) |
C1 | 0.0239 (7) | 0.0227 (7) | 0.0157 (6) | −0.0034 (5) | 0.0017 (5) | −0.0030 (5) |
C2 | 0.0216 (7) | 0.0237 (7) | 0.0164 (6) | −0.0028 (5) | −0.0001 (5) | −0.0020 (5) |
C3 | 0.0261 (8) | 0.0264 (7) | 0.0270 (8) | −0.0045 (6) | 0.0024 (6) | 0.0027 (6) |
C4 | 0.0228 (7) | 0.0349 (8) | 0.0347 (8) | −0.0079 (6) | 0.0074 (6) | −0.0007 (7) |
C5 | 0.0220 (7) | 0.0327 (8) | 0.0352 (8) | 0.0031 (6) | 0.0040 (6) | −0.0019 (7) |
C6 | 0.0281 (8) | 0.0232 (7) | 0.0283 (8) | −0.0003 (6) | 0.0014 (6) | 0.0004 (6) |
C11 | 0.0263 (7) | 0.0180 (7) | 0.0263 (7) | −0.0016 (5) | 0.0075 (6) | −0.0040 (6) |
C21 | 0.0222 (7) | 0.0209 (7) | 0.0240 (7) | −0.0040 (5) | −0.0019 (6) | −0.0029 (6) |
O1W | 0.0325 (6) | 0.0351 (7) | 0.0400 (7) | −0.0093 (5) | −0.0061 (6) | 0.0099 (5) |
Cl4—C4 | 1.7401 (16) | C5A—H52A | 0.9900 |
Cl5—C5 | 1.7408 (16) | C6A—H62A | 0.9900 |
O11—C11 | 1.2675 (18) | C6A—H61A | 0.9900 |
O12—C11 | 1.2431 (18) | C2B—C3B | 1.514 (2) |
O21—C21 | 1.2635 (17) | C3B—C4B | 1.522 (3) |
O22—C21 | 1.2522 (17) | C4B—C5B | 1.528 (3) |
O1W—H11W | 0.82 (2) | C5B—C6B | 1.517 (2) |
O1W—H12W | 0.84 (2) | C2B—H21B | 0.9900 |
N1A—C6A | 1.491 (2) | C2B—H22B | 0.9900 |
N1A—C2A | 1.4960 (19) | C3B—H31B | 0.9900 |
N1A—H11A | 0.90 (2) | C3B—H32B | 0.9900 |
N1A—H12A | 0.914 (19) | C4B—H41B | 0.9900 |
N1B—C6B | 1.490 (2) | C4B—H42B | 0.9900 |
N1B—C2B | 1.495 (2) | C5B—H52B | 0.9900 |
N1B—H12B | 0.975 (19) | C5B—H51B | 0.9900 |
N1B—H11B | 0.896 (17) | C6B—H62B | 0.9900 |
C2A—C3A | 1.519 (2) | C6B—H61B | 0.9900 |
C3A—C4A | 1.528 (2) | C1—C11 | 1.522 (2) |
C4A—C5A | 1.519 (2) | C1—C2 | 1.4080 (19) |
C5A—C6A | 1.523 (2) | C1—C6 | 1.391 (2) |
C2A—H22A | 0.9900 | C2—C21 | 1.522 (2) |
C2A—H21A | 0.9900 | C2—C3 | 1.394 (2) |
C3A—H31A | 0.9900 | C3—C4 | 1.386 (2) |
C3A—H32A | 0.9900 | C4—C5 | 1.396 (2) |
C4A—H41A | 0.9900 | C5—C6 | 1.388 (2) |
C4A—H42A | 0.9900 | C3—H3 | 0.9500 |
C5A—H51A | 0.9900 | C6—H6 | 0.9500 |
H11W—O1W—H12W | 109 (2) | C3B—C2B—H21B | 110.00 |
C2A—N1A—C6A | 112.57 (12) | N1B—C2B—H21B | 110.00 |
C6A—N1A—H11A | 107.3 (11) | H21B—C2B—H22B | 108.00 |
H11A—N1A—H12A | 111.6 (16) | C3B—C2B—H22B | 110.00 |
C2A—N1A—H12A | 107.2 (11) | C2B—C3B—H32B | 109.00 |
C2A—N1A—H11A | 109.7 (11) | C4B—C3B—H31B | 109.00 |
C6A—N1A—H12A | 108.6 (11) | C2B—C3B—H31B | 109.00 |
C2B—N1B—C6B | 112.55 (12) | H31B—C3B—H32B | 108.00 |
C2B—N1B—H11B | 109.9 (11) | C4B—C3B—H32B | 109.00 |
H11B—N1B—H12B | 108.0 (15) | C3B—C4B—H41B | 110.00 |
C6B—N1B—H11B | 111.6 (12) | C5B—C4B—H41B | 110.00 |
C6B—N1B—H12B | 110.0 (11) | C5B—C4B—H42B | 110.00 |
C2B—N1B—H12B | 104.5 (11) | H41B—C4B—H42B | 108.00 |
N1A—C2A—C3A | 110.25 (13) | C3B—C4B—H42B | 110.00 |
C2A—C3A—C4A | 110.88 (13) | C4B—C5B—H52B | 109.00 |
C3A—C4A—C5A | 109.92 (13) | C6B—C5B—H51B | 109.00 |
C4A—C5A—C6A | 110.74 (13) | C4B—C5B—H51B | 109.00 |
N1A—C6A—C5A | 111.02 (13) | H51B—C5B—H52B | 108.00 |
H21A—C2A—H22A | 108.00 | C6B—C5B—H52B | 109.00 |
N1A—C2A—H21A | 110.00 | N1B—C6B—H62B | 110.00 |
C3A—C2A—H21A | 110.00 | C5B—C6B—H61B | 110.00 |
C3A—C2A—H22A | 110.00 | C5B—C6B—H62B | 110.00 |
N1A—C2A—H22A | 110.00 | H61B—C6B—H62B | 108.00 |
C2A—C3A—H32A | 109.00 | N1B—C6B—H61B | 110.00 |
C2A—C3A—H31A | 109.00 | C2—C1—C6 | 119.57 (13) |
C4A—C3A—H32A | 109.00 | C2—C1—C11 | 122.20 (12) |
C4A—C3A—H31A | 109.00 | C6—C1—C11 | 118.00 (12) |
H31A—C3A—H32A | 108.00 | C1—C2—C21 | 120.70 (12) |
H41A—C4A—H42A | 108.00 | C3—C2—C21 | 119.76 (12) |
C3A—C4A—H42A | 110.00 | C1—C2—C3 | 119.53 (13) |
C5A—C4A—H41A | 110.00 | C2—C3—C4 | 120.59 (14) |
C5A—C4A—H42A | 110.00 | Cl4—C4—C3 | 119.00 (12) |
C3A—C4A—H41A | 110.00 | Cl4—C4—C5 | 121.28 (12) |
C4A—C5A—H52A | 110.00 | C3—C4—C5 | 119.71 (14) |
C6A—C5A—H52A | 110.00 | Cl5—C5—C6 | 118.37 (12) |
H51A—C5A—H52A | 108.00 | C4—C5—C6 | 120.23 (14) |
C4A—C5A—H51A | 110.00 | Cl5—C5—C4 | 121.41 (12) |
C6A—C5A—H51A | 109.00 | C1—C6—C5 | 120.34 (14) |
N1A—C6A—H62A | 109.00 | O11—C11—C1 | 117.21 (12) |
N1A—C6A—H61A | 109.00 | O12—C11—C1 | 116.31 (12) |
C5A—C6A—H62A | 109.00 | O11—C11—O12 | 126.39 (14) |
C5A—C6A—H61A | 109.00 | O21—C21—C2 | 115.02 (12) |
H61A—C6A—H62A | 108.00 | O22—C21—C2 | 117.83 (12) |
N1B—C2B—C3B | 110.24 (13) | O21—C21—O22 | 127.12 (13) |
C2B—C3B—C4B | 110.89 (14) | C2—C3—H3 | 120.00 |
C3B—C4B—C5B | 109.92 (15) | C4—C3—H3 | 120.00 |
C4B—C5B—C6B | 111.52 (15) | C1—C6—H6 | 120.00 |
N1B—C6B—C5B | 110.65 (13) | C5—C6—H6 | 120.00 |
N1B—C2B—H22B | 110.00 | ||
C6A—N1A—C2A—C3A | 56.24 (17) | C2—C1—C11—O11 | −118.74 (15) |
C2A—N1A—C6A—C5A | −55.92 (17) | C2—C1—C11—O12 | 64.50 (18) |
C6B—N1B—C2B—C3B | −57.31 (16) | C6—C1—C11—O11 | 66.86 (17) |
C2B—N1B—C6B—C5B | 56.01 (17) | C6—C1—C11—O12 | −109.90 (15) |
N1A—C2A—C3A—C4A | −56.58 (17) | C1—C2—C3—C4 | −1.1 (2) |
C2A—C3A—C4A—C5A | 57.19 (18) | C21—C2—C3—C4 | 177.83 (13) |
C3A—C4A—C5A—C6A | −56.35 (17) | C1—C2—C21—O21 | 40.40 (18) |
C4A—C5A—C6A—N1A | 55.68 (17) | C1—C2—C21—O22 | −141.41 (13) |
N1B—C2B—C3B—C4B | 57.22 (18) | C3—C2—C21—O21 | −138.54 (13) |
C2B—C3B—C4B—C5B | −56.38 (19) | C3—C2—C21—O22 | 39.65 (19) |
C3B—C4B—C5B—C6B | 55.2 (2) | C2—C3—C4—Cl4 | −179.89 (11) |
C4B—C5B—C6B—N1B | −54.75 (18) | C2—C3—C4—C5 | −0.3 (2) |
C6—C1—C2—C3 | 2.2 (2) | Cl4—C4—C5—Cl5 | −0.3 (2) |
C6—C1—C2—C21 | −176.73 (13) | Cl4—C4—C5—C6 | −179.77 (12) |
C11—C1—C2—C3 | −172.11 (13) | C3—C4—C5—Cl5 | −179.84 (12) |
C11—C1—C2—C21 | 8.95 (19) | C3—C4—C5—C6 | 0.7 (2) |
C2—C1—C6—C5 | −1.9 (2) | Cl5—C5—C6—C1 | −179.07 (11) |
C11—C1—C6—C5 | 172.68 (13) | C4—C5—C6—C1 | 0.4 (2) |
D—H···A | D—H | H···A | D···A | D—H···A |
N1A—H11A···O21i | 0.90 (2) | 1.80 (2) | 2.6820 (17) | 164.0 (17) |
N1A—H12A···O11 | 0.914 (19) | 1.907 (19) | 2.8085 (17) | 168.4 (16) |
N1B—H11B···O11i | 0.896 (17) | 1.917 (17) | 2.8054 (16) | 170.7 (16) |
N1B—H12B···O1W | 0.975 (19) | 1.882 (19) | 2.7866 (18) | 153.1 (15) |
O1W—H11W···O12 | 0.82 (2) | 1.93 (2) | 2.7490 (17) | 176 (2) |
O1W—H12W···O22ii | 0.84 (2) | 1.96 (2) | 2.7639 (17) | 162 (2) |
Symmetry codes: (i) −x, y−1/2, −z+1/2; (ii) −x, −y+2, −z. |
Lewis base type | structure type** | C1–C11 | C2–C21 | C1–C2–C21 | C2–C1–C11 | O12–H···O21 | C1–C2–C21–O22 | C2–C1–C11–O11 |
TEAa | 0 | 1.5366 (19) | 1.5344 (19) | 128.16 (11) | 129.73 (11) | 2.4223 (14) | 178.46 (13) | 179.64 (13) |
DEAa | 2 | 1.531 (3) | 1.521 (3) | 128.33 (17) | 128.49 (16) | 2.388 (2) | -172.41 (19) | 175.50 (19) |
IPAb | 1 | 1.5189 (18) | 1.5297 (18) | 128.32 (11) | 128.14 (11) | 2.4507 (16) | 161.01 (13) | -156.69 (13) |
DIPAc | 1 | 1.523 (3) | 1.516 (3) | 128.5 (2) | 128.2 (2) | 2.381 (3) | -170.8 (2) | -176.7 (2) |
HMTc | 1 | 1.529 (9) | 1.523 (8) | 129.3 (5) | 127.8 (5) | 2.381 (8) | -173.7 (6) | 173.6 (5) |
INIPAd | 1 | 1.522 (4) | 1.534 (4) | 128.8 (2) | 128.2 (2) | 2.392 (3) | -174.6 (3) | 174.2 (3) |
TMAe | 1 | 1.528 (3) | 1.529 (3) | 128.9 (2) | 128.9 (2) | 2.380 (3) | 180 | 180 |
TBAf | 0 | 1.523 (13) | 1.529 (14) | 128.3 (9) | 128.9 (8) | 2.34 (1) | 173 (1) | 168 (1) |
BRUg | 0 | 1.523 (3) | 1.535 (3) | 128.9 (2) | 128.4 (2) | 2.441 (3) | -177.8 (2) | 163.9 (2) |
NICAh | 0 | 1.531 (3) | 1.528 (3) | 127.88 (16) | 128.93 (16) | 2.410 (2) | 172.58 (18) | -178.68 (19) |
INICAh | 1 | 1.521 (8) | 1.515 (11) | 128.3 (5) | 128.0 (5) | 2.393 (8) | -178.6 (7) | 173.0 (7) |
AMPMh | 0 | 1.527 (2) | 1.532 (2) | 128.72 (14) | 128.90 (14) | 2.4037 (19) | -179.70 (16) | -170.16 (16) |
PMPYi | 1 | 1.527 (5) | 1.531 (5) | 128.9 (3) | 128.8 (3) | 2.376 (4) | 169.9 (3) | -173.2 (3) |
TFMANj | 2 | 1.5161 (19) | 1.520 (2) | 128.35 (13) | 128.69 (12) | 2.3908 (17) | -179.04 (16) | 179.50 (16) |
8-AQk | 1 | 1.525 (2) | 1.534 (2) | 129.27 (14) | 128.36 (14) | 2.3922 (18) | -175.88 (15) | 174.38 (15) |
8-HQk | 1 | 1.527 (3) | 1.518 (3) | 127.97 (19) | 128.88 (19) | 2.389 (2) | -176.6 (2) | 171.3 (2) |
BTMAPl | 0 | 1.536 (2) | 1.534 (2) | 129.09 (15) | 129.00 (14) | 2.4004 (19) | 172.41 (15) | 179.32 (16) |
PHENm | 0 | 1.538 (2) | 1.536 (3) | 128.55 (15) | 129.18 (16) | 2.4054 (19) | -179.53 (16) | -168.30 (16) |
QACn* | 2 | 1.527 (7) | 1.527 (7) | 129.6 (5) | 128.4 (4) | 2.366 (7) | 177.0 (5) | -172.4 (5) |
QACn* | 2 | 1.522 (8) | 1.511 (6) | 128.2 (4) | 129.0 (4) | 2.377 (5) | 178.5 (5) | -174.2 (5) |
(a) this work [TEA is triethylamine, DEA is diethylamine]; (b) Smith & Wermuth (2010b) [IPA is isopropylamine]; (c) Smith & Wermuth (2010a) [DIPA is diisopropylamine, HMT is hexamethylenetetramine]; (d) Smith & Wermuth (2010e) [INIPA is isonipecotamide]; (e) Bozkurt et al. (2006) [TMA is tetramethylammonium ion]; (f) Mattes & Dorau (1986) [TBA is tetra(n-butyl)ammonium ion]; (g) Smith et al. (2007) [BRU is brucine]; (h) Smith et al. (2009a) [NICA is nicotinamide, INICA is isonicotinamide, AMPM is 2-aminopyrimidine]; (i) Smith & Wermuth (2010d) [PMPY is 4-methylpyridine]; (j) Odabaşoğlu & Büyükgüngör (2007) [TFMAN is 3-(trifluoromethyl)aniline]; (k) Smith et al. (2008b) [8-AQ is 8-aminoquinoline, 8-HQ is 8-hydroxyquinoline]; (l) Mallinson et al. (2003); Parkin et al. (2007) [BTMAP is 1,8-bis(trimethylamino)naphthalene]; (m) Smith et al. (2009c) [PHEN is 1,10-phenanthroline]; (n) Smith et al. (2009) [QAC is quinacrine]; (*) For the quinacrine salt, there are two independent DCPA anions in the asymmetric unit; (**) 0 = zero-dimensional; 1 = one-dimensional; 2 = two-dimensional. |