Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805002503/hg6129sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536805002503/hg6129Isup2.hkl |
CCDC reference: 269784
Data collection: APEX2 (Bruker–Nonius, 2004); cell refinement: SAINT (Bruker, 2003); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2000); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.
C14H17N3O22+·2ClO4− | F(000) = 944 |
Mr = 458.21 | Dx = 1.678 Mg m−3 |
Monoclinic, P2/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2yc | Cell parameters from 2492 reflections |
a = 14.1367 (12) Å | θ = 2.5–21.2° |
b = 7.9021 (8) Å | µ = 0.42 mm−1 |
c = 16.8034 (16) Å | T = 180 K |
β = 104.907 (3)° | Plate, colourless |
V = 1813.9 (3) Å3 | 0.12 × 0.08 × 0.01 mm |
Z = 4 |
Bruker–Nonius X8APEX-II CCD diffractometer | 2175 independent reflections |
Radiation source: fine-focus sealed tube | 1542 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.068 |
thin–slice ω and φ scans | θmax = 22.0°, θmin = 3.6° |
Absorption correction: multi-scan (SADABS; Sheldrick, 2003) | h = −14→14 |
Tmin = 0.665, Tmax = 0.996 | k = −8→8 |
15019 measured reflections | l = −17→17 |
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)] = 0.053 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.143 | H-atom parameters constrained |
S = 1.07 | w = 1/[σ2(Fo2) + (0.0784P)2 + 1.4336P] where P = (Fo2 + 2Fc2)/3 |
2175 reflections | (Δ/σ)max < 0.001 |
290 parameters | Δρmax = 0.49 e Å−3 |
71 restraints | Δρmin = −0.40 e Å−3 |
Experimental. Crystal was best available from the batch, but a little on the small side. As a result, diffraction was weak. The data are truncated to 0.95 Å resolution and the structure is therefore of relatively low precision. H atoms bound to N evident in Fourier maps but placed in calculated positions (on account of the relatively low resolution and the associated low data:parameter ratio). H atom of carboxyl group located in difference Fourier then moved along the O2—H2 bond vector to give O—H = 0.85 Å. Subsequently allowed to ride on O2 with Uiso(H) = 1.5 x Ueq(O).? |
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 | Occ. (<1) | |
O1 | 0.5944 (3) | 0.0907 (5) | 0.4784 (2) | 0.0362 (11) | |
O2 | 0.4933 (3) | 0.2109 (5) | 0.5458 (2) | 0.0363 (11) | |
H2 | 0.4685 | 0.1128 | 0.5353 | 0.054* | |
N1 | 0.8369 (4) | 0.4331 (6) | 0.6800 (3) | 0.0392 (14) | |
H1B | 0.8159 | 0.5130 | 0.6432 | 0.047* | |
N2 | 0.7261 (3) | 0.3670 (6) | 0.5196 (3) | 0.0311 (12) | |
N3 | 0.7346 (4) | 0.6732 (6) | 0.4385 (3) | 0.0366 (13) | |
H3B | 0.7716 | 0.6523 | 0.4883 | 0.044* | |
C1 | 0.8751 (5) | 0.4798 (9) | 0.7586 (4) | 0.0448 (17) | |
H1A | 0.8809 | 0.5961 | 0.7734 | 0.054* | |
C2 | 0.9051 (5) | 0.3580 (9) | 0.8164 (4) | 0.0421 (17) | |
H2A | 0.9318 | 0.3890 | 0.8724 | 0.050* | |
C3 | 0.8973 (5) | 0.1905 (9) | 0.7946 (4) | 0.0470 (18) | |
H3A | 0.9186 | 0.1053 | 0.8352 | 0.056* | |
C4 | 0.8578 (5) | 0.1459 (8) | 0.7120 (4) | 0.0429 (17) | |
H4A | 0.8511 | 0.0300 | 0.6965 | 0.051* | |
C5 | 0.8288 (4) | 0.2690 (7) | 0.6538 (4) | 0.0311 (15) | |
C6 | 0.7922 (4) | 0.2373 (7) | 0.5630 (3) | 0.0332 (15) | |
H6A | 0.8490 | 0.2296 | 0.5389 | 0.040* | |
H6B | 0.7580 | 0.1268 | 0.5545 | 0.040* | |
C7 | 0.7171 (5) | 0.3680 (7) | 0.4306 (4) | 0.0379 (16) | |
H7A | 0.6650 | 0.2878 | 0.4032 | 0.045* | |
H7B | 0.7794 | 0.3289 | 0.4202 | 0.045* | |
C8 | 0.6931 (5) | 0.5409 (8) | 0.3938 (4) | 0.0374 (16) | |
C9 | 0.6363 (5) | 0.5720 (8) | 0.3158 (4) | 0.0404 (17) | |
H9A | 0.6044 | 0.4814 | 0.2823 | 0.048* | |
C10 | 0.6257 (5) | 0.7361 (9) | 0.2863 (4) | 0.0469 (18) | |
H10A | 0.5878 | 0.7572 | 0.2318 | 0.056* | |
C11 | 0.6695 (6) | 0.8703 (9) | 0.3351 (4) | 0.0506 (19) | |
H11A | 0.6621 | 0.9832 | 0.3150 | 0.061* | |
C12 | 0.7247 (5) | 0.8346 (8) | 0.4145 (4) | 0.0426 (17) | |
H12A | 0.7547 | 0.9228 | 0.4507 | 0.051* | |
C14 | 0.6303 (4) | 0.3679 (7) | 0.5376 (4) | 0.0336 (15) | |
H14A | 0.5916 | 0.4626 | 0.5069 | 0.040* | |
H14B | 0.6401 | 0.3917 | 0.5970 | 0.040* | |
C15 | 0.5709 (4) | 0.2102 (8) | 0.5176 (3) | 0.0296 (14) | |
Cl1 | 0.65778 (11) | 0.78596 (19) | 0.66566 (9) | 0.0377 (5) | |
O11 | 0.7148 (3) | 0.7652 (5) | 0.7485 (2) | 0.0442 (11) | |
O12 | 0.6259 (3) | 0.9598 (5) | 0.6522 (2) | 0.0518 (13) | |
O13 | 0.7175 (3) | 0.7461 (5) | 0.6106 (2) | 0.0495 (12) | |
O14 | 0.5746 (3) | 0.6771 (6) | 0.6497 (3) | 0.0537 (13) | |
Cl2 | 0.97009 (12) | 0.7695 (2) | 0.57606 (11) | 0.0487 (6) | |
O21 | 0.9149 (3) | 0.6172 (5) | 0.5635 (3) | 0.0687 (15) | |
O22 | 1.0681 (6) | 0.7609 (17) | 0.6188 (7) | 0.058 (5) | 0.40 |
O23 | 0.9772 (9) | 0.7831 (14) | 0.4847 (5) | 0.071 (4) | 0.40 |
O24 | 0.9222 (10) | 0.9166 (12) | 0.5853 (8) | 0.063 (5) | 0.40 |
O22A | 0.9714 (6) | 0.7917 (10) | 0.6673 (4) | 0.076 (3) | 0.60 |
O23A | 1.0654 (5) | 0.7552 (13) | 0.5742 (6) | 0.070 (3) | 0.60 |
O24A | 0.9175 (6) | 0.9087 (10) | 0.5367 (6) | 0.065 (3) | 0.60 |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.033 (3) | 0.038 (3) | 0.043 (3) | −0.0029 (19) | 0.019 (2) | −0.002 (2) |
O2 | 0.031 (3) | 0.042 (3) | 0.043 (3) | −0.0045 (19) | 0.022 (2) | −0.0077 (19) |
N1 | 0.035 (3) | 0.041 (4) | 0.042 (4) | −0.004 (2) | 0.009 (3) | −0.001 (3) |
N2 | 0.032 (3) | 0.033 (3) | 0.033 (3) | 0.001 (2) | 0.017 (2) | −0.003 (2) |
N3 | 0.048 (4) | 0.030 (3) | 0.038 (3) | −0.004 (3) | 0.022 (3) | −0.006 (3) |
C1 | 0.037 (4) | 0.048 (5) | 0.048 (5) | −0.005 (3) | 0.009 (3) | −0.010 (4) |
C2 | 0.033 (4) | 0.048 (5) | 0.046 (4) | 0.003 (3) | 0.010 (3) | 0.004 (4) |
C3 | 0.035 (4) | 0.060 (6) | 0.049 (5) | 0.008 (3) | 0.016 (3) | 0.011 (4) |
C4 | 0.038 (4) | 0.033 (4) | 0.063 (5) | 0.004 (3) | 0.023 (4) | 0.003 (4) |
C5 | 0.026 (4) | 0.027 (4) | 0.044 (4) | −0.003 (3) | 0.016 (3) | −0.004 (3) |
C6 | 0.027 (4) | 0.034 (4) | 0.040 (4) | 0.001 (3) | 0.012 (3) | −0.003 (3) |
C7 | 0.043 (4) | 0.034 (4) | 0.045 (4) | −0.001 (3) | 0.026 (3) | −0.003 (3) |
C8 | 0.046 (4) | 0.034 (4) | 0.043 (4) | −0.003 (3) | 0.030 (4) | −0.004 (3) |
C9 | 0.044 (4) | 0.043 (5) | 0.038 (4) | 0.005 (3) | 0.017 (3) | −0.003 (3) |
C10 | 0.052 (5) | 0.060 (5) | 0.037 (4) | 0.012 (4) | 0.026 (3) | 0.006 (4) |
C11 | 0.076 (5) | 0.040 (5) | 0.050 (5) | −0.001 (4) | 0.042 (4) | −0.001 (4) |
C12 | 0.064 (5) | 0.028 (4) | 0.048 (5) | 0.000 (3) | 0.035 (4) | −0.002 (3) |
C14 | 0.037 (4) | 0.028 (4) | 0.044 (4) | 0.000 (3) | 0.025 (3) | −0.005 (3) |
C15 | 0.027 (4) | 0.042 (4) | 0.025 (3) | 0.003 (3) | 0.016 (3) | 0.001 (3) |
Cl1 | 0.0446 (11) | 0.0415 (11) | 0.0301 (10) | 0.0044 (7) | 0.0153 (7) | −0.0009 (7) |
O11 | 0.051 (3) | 0.050 (3) | 0.028 (3) | 0.005 (2) | 0.005 (2) | 0.003 (2) |
O12 | 0.072 (3) | 0.039 (3) | 0.046 (3) | 0.019 (2) | 0.018 (2) | 0.006 (2) |
O13 | 0.056 (3) | 0.058 (3) | 0.045 (3) | 0.007 (2) | 0.032 (2) | −0.005 (2) |
O14 | 0.051 (3) | 0.059 (3) | 0.052 (3) | −0.013 (2) | 0.016 (2) | −0.002 (2) |
Cl2 | 0.0344 (11) | 0.0378 (11) | 0.0711 (13) | 0.0015 (8) | 0.0083 (9) | 0.0024 (9) |
O21 | 0.057 (3) | 0.046 (3) | 0.109 (4) | −0.006 (2) | 0.032 (3) | 0.014 (3) |
O22 | 0.036 (7) | 0.080 (8) | 0.058 (8) | −0.002 (6) | 0.011 (6) | 0.029 (7) |
O23 | 0.095 (9) | 0.095 (8) | 0.031 (6) | −0.036 (7) | 0.033 (6) | −0.005 (6) |
O24 | 0.062 (8) | 0.050 (8) | 0.088 (10) | 0.017 (6) | 0.040 (8) | −0.016 (7) |
O22A | 0.075 (6) | 0.074 (6) | 0.077 (6) | 0.004 (5) | 0.017 (4) | −0.023 (5) |
O23A | 0.045 (6) | 0.083 (6) | 0.099 (8) | 0.012 (4) | 0.051 (5) | 0.049 (6) |
O24A | 0.052 (6) | 0.051 (6) | 0.096 (7) | 0.012 (4) | 0.026 (6) | 0.035 (5) |
O1—C15 | 1.244 (6) | C7—C8 | 1.502 (8) |
O2—C15 | 1.303 (6) | C7—H7A | 0.990 |
O2—H2 | 0.850 | C7—H7B | 0.990 |
N1—C1 | 1.344 (8) | C8—C9 | 1.371 (8) |
N1—C5 | 1.364 (7) | C9—C10 | 1.382 (9) |
N1—H1B | 0.880 | C9—H9A | 0.950 |
N2—C6 | 1.451 (7) | C10—C11 | 1.386 (9) |
N2—C14 | 1.462 (7) | C10—H10A | 0.950 |
N2—C7 | 1.469 (7) | C11—C12 | 1.390 (9) |
N3—C8 | 1.332 (7) | C11—H11A | 0.950 |
N3—C12 | 1.334 (8) | C12—H12A | 0.950 |
N3—H3B | 0.880 | C14—C15 | 1.491 (8) |
C1—C2 | 1.356 (9) | C14—H14A | 0.990 |
C1—H1A | 0.950 | C14—H14B | 0.990 |
C2—C3 | 1.371 (9) | Cl1—O14 | 1.426 (4) |
C2—H2A | 0.950 | Cl1—O11 | 1.428 (4) |
C3—C4 | 1.401 (9) | Cl1—O13 | 1.439 (4) |
C3—H3A | 0.950 | Cl1—O12 | 1.445 (4) |
C4—C5 | 1.366 (8) | Cl2—O24 | 1.374 (8) |
C4—H4A | 0.950 | Cl2—O22 | 1.389 (8) |
C5—C6 | 1.500 (8) | Cl2—O21 | 1.420 (4) |
C6—H6A | 0.990 | Cl2—O23 | 1.568 (7) |
C6—H6B | 0.990 | ||
C15—O2—H2 | 105.2 | N3—C8—C9 | 117.6 (6) |
C1—N1—C5 | 123.9 (5) | N3—C8—C7 | 117.5 (6) |
C1—N1—H1B | 118.1 | C9—C8—C7 | 124.8 (6) |
C5—N1—H1B | 118.1 | C8—C9—C10 | 119.6 (6) |
C6—N2—C14 | 114.2 (4) | C8—C9—H9A | 120.2 |
C6—N2—C7 | 113.1 (4) | C10—C9—H9A | 120.2 |
C14—N2—C7 | 111.6 (4) | C9—C10—C11 | 121.0 (6) |
C8—N3—C12 | 125.6 (6) | C9—C10—H10A | 119.5 |
C8—N3—H3B | 117.2 | C11—C10—H10A | 119.5 |
C12—N3—H3B | 117.2 | C10—C11—C12 | 117.9 (6) |
N1—C1—C2 | 118.8 (6) | C10—C11—H11A | 121.1 |
N1—C1—H1A | 120.6 | C12—C11—H11A | 121.1 |
C2—C1—H1A | 120.6 | N3—C12—C11 | 118.3 (6) |
C1—C2—C3 | 120.3 (6) | N3—C12—H12A | 120.9 |
C1—C2—H2A | 119.8 | C11—C12—H12A | 120.9 |
C3—C2—H2A | 119.8 | N2—C14—C15 | 116.6 (5) |
C2—C3—C4 | 119.5 (6) | N2—C14—H14A | 108.2 |
C2—C3—H3A | 120.3 | C15—C14—H14A | 108.2 |
C4—C3—H3A | 120.3 | N2—C14—H14B | 108.2 |
C5—C4—C3 | 120.0 (6) | C15—C14—H14B | 108.2 |
C5—C4—H4A | 120.0 | H14A—C14—H14B | 107.3 |
C3—C4—H4A | 120.0 | O1—C15—O2 | 124.1 (5) |
N1—C5—C4 | 117.5 (6) | O1—C15—C14 | 122.8 (5) |
N1—C5—C6 | 117.7 (5) | O2—C15—C14 | 113.1 (5) |
C4—C5—C6 | 124.8 (5) | O14—Cl1—O11 | 110.3 (3) |
N2—C6—C5 | 113.7 (5) | O14—Cl1—O13 | 109.8 (3) |
N2—C6—H6A | 108.8 | O11—Cl1—O13 | 109.0 (3) |
C5—C6—H6A | 108.8 | O14—Cl1—O12 | 109.6 (3) |
N2—C6—H6B | 108.8 | O11—Cl1—O12 | 109.7 (2) |
C5—C6—H6B | 108.8 | O13—Cl1—O12 | 108.6 (2) |
H6A—C6—H6B | 107.7 | O24—Cl2—O22 | 116.0 (7) |
N2—C7—C8 | 112.0 (5) | O24—Cl2—O21 | 117.7 (6) |
N2—C7—H7A | 109.2 | O22—Cl2—O21 | 118.2 (6) |
C8—C7—H7A | 109.2 | O24—Cl2—O23 | 102.2 (6) |
N2—C7—H7B | 109.2 | O22—Cl2—O23 | 101.7 (6) |
C8—C7—H7B | 109.2 | O21—Cl2—O23 | 94.8 (4) |
H7A—C7—H7B | 107.9 | ||
C5—N1—C1—C2 | −1.9 (9) | C12—N3—C8—C9 | 0.9 (8) |
N1—C1—C2—C3 | 0.6 (9) | C12—N3—C8—C7 | 177.2 (5) |
C1—C2—C3—C4 | −0.1 (9) | N2—C7—C8—N3 | 37.3 (7) |
C2—C3—C4—C5 | 1.0 (9) | N2—C7—C8—C9 | −146.7 (6) |
C1—N1—C5—C4 | 2.8 (8) | N3—C8—C9—C10 | 1.2 (8) |
C1—N1—C5—C6 | −175.1 (5) | C7—C8—C9—C10 | −174.8 (5) |
C3—C4—C5—N1 | −2.2 (8) | C8—C9—C10—C11 | −1.7 (9) |
C3—C4—C5—C6 | 175.4 (5) | C9—C10—C11—C12 | 0.3 (9) |
C14—N2—C6—C5 | −70.4 (6) | C8—N3—C12—C11 | −2.3 (8) |
C7—N2—C6—C5 | 160.5 (5) | C10—C11—C12—N3 | 1.7 (9) |
N1—C5—C6—N2 | −29.4 (7) | C6—N2—C14—C15 | −59.9 (6) |
C4—C5—C6—N2 | 153.0 (5) | C7—N2—C14—C15 | 69.9 (6) |
C6—N2—C7—C8 | −151.7 (5) | N2—C14—C15—O1 | −8.8 (8) |
C14—N2—C7—C8 | 77.9 (6) | N2—C14—C15—O2 | 170.8 (5) |
D—H···A | D—H | H···A | D···A | D—H···A |
O2—H2···O1i | 0.85 | 1.82 | 2.669 (5) | 173 |
N1—H1B···O13 | 0.88 | 2.29 | 3.052 (7) | 145 |
N1—H1B···O21 | 0.88 | 2.32 | 2.877 (7) | 121 |
N3—H3B···O13 | 0.88 | 2.48 | 3.017 (6) | 120 |
N3—H3B···O21 | 0.88 | 2.11 | 2.889 (7) | 147 |
Symmetry code: (i) −x+1, −y, −z+1. |