Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S160053680201022X/ci6132sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S160053680201022X/ci6132Isup2.hkl |
CCDC reference: 189898
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.002 Å
- R factor = 0.042
- wR factor = 0.136
- Data-to-parameter ratio = 28.7
checkCIF results
No syntax errors found ADDSYM reports no extra symmetry General Notes
REFLT_03 From the CIF: _diffrn_reflns_theta_max 35.87 From the CIF: _reflns_number_total 6750 Count of symmetry unique reflns 4571 Completeness (_total/calc) 147.67% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 2179 Fraction of Friedel pairs measured 0.477 Are heavy atom types Z>Si present yes WARNING: Large fraction of Friedel related reflns may be needed to determine absolute structure
Data collection: SMART (Bruker, 1998); cell refinement: SAINT (Bruker, 1998); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 1999); software used to prepare material for publication: SHELXL97.
C6H15N4O2+·Cl− | Z = 2 |
Mr = 210.67 | F(000) = 224 |
Triclinic, P1 | Dx = 1.438 Mg m−3 Dm = 1.435 Mg m−3 Dm measured by flotation in carbon tetrachloride and xylene |
a = 5.1263 (8) Å | Mo Kα radiation, λ = 0.71074 Å |
b = 9.461 (1) Å | Cell parameters from 9359 reflections |
c = 10.322 (2) Å | θ = 2.4–35.3° |
α = 88.138 (5)° | µ = 0.37 mm−1 |
β = 76.447 (4)° | T = 293 K |
γ = 89.745 (5)° | Block, colorless |
V = 486.37 (13) Å3 | 0.8 × 0.5 × 0.5 mm |
Bruker SMART CCD diffractometer | 6750 independent reflections |
Radiation source: fine-focus sealed tube | 6192 reflections with I > \2s(I) |
Graphite monochromator | Rint = 0.024 |
Detector resolution: 8.33 pixels mm-1 | θmax = 35.9°, θmin = 2.0° |
ω scans | h = −8→8 |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | k = −15→15 |
Tmin = 0.74, Tmax = 0.83 | l = −16→16 |
10067 measured reflections |
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)] = 0.042 | H-atom parameters constrained |
wR(F2) = 0.136 | w = 1/[σ2(Fo2) + (0.1P)2] where P = (Fo2 + 2Fc2)/3 |
S = 1.04 | (Δ/σ)max < 0.001 |
6750 reflections | Δρmax = 0.48 e Å−3 |
235 parameters | Δρmin = −0.28 e Å−3 |
3 restraints | Absolute structure: Flack (1983) |
Primary atom site location: structure-invariant direct methods | Absolute structure parameter: 0.12 (4) |
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 | ||
O1A | 0.3939 (2) | 0.57357 (12) | 1.01021 (12) | 0.0255 (2) | |
O1B | 0.0035 (2) | 0.65441 (14) | 0.97668 (14) | 0.0292 (2) | |
C11 | 0.2490 (3) | 0.66502 (14) | 0.96937 (13) | 0.0186 (2) | |
C12 | 0.3919 (3) | 0.79894 (14) | 0.89989 (14) | 0.0199 (2) | |
H12 | 0.2567 | 0.8697 | 0.8907 | 0.024* | |
N11 | 0.5673 (3) | 0.85735 (14) | 0.98226 (14) | 0.0250 (2) | |
H11A | 0.4687 | 0.8751 | 1.0632 | 0.038* | |
H11B | 0.6440 | 0.9371 | 0.9436 | 0.038* | |
H11C | 0.6938 | 0.7947 | 0.9891 | 0.038* | |
C13 | 0.5659 (3) | 0.76959 (18) | 0.76201 (15) | 0.0271 (3) | |
H13A | 0.6317 | 0.8585 | 0.7170 | 0.032* | |
H13B | 0.7199 | 0.7138 | 0.7716 | 0.032* | |
C14 | 0.4115 (4) | 0.69091 (19) | 0.67734 (16) | 0.0288 (3) | |
H14A | 0.2377 | 0.7350 | 0.6846 | 0.035* | |
H14B | 0.3815 | 0.5941 | 0.7112 | 0.035* | |
N12 | 0.4039 (3) | 0.60647 (18) | 0.46169 (14) | 0.0321 (3) | |
H12A | 0.2622 | 0.5654 | 0.5087 | 0.039* | |
C15 | 0.5609 (4) | 0.6909 (2) | 0.53119 (16) | 0.0290 (3) | |
H15A | 0.5805 | 0.7867 | 0.4939 | 0.035* | |
H15B | 0.7382 | 0.6505 | 0.5225 | 0.035* | |
C16 | 0.4623 (3) | 0.58825 (17) | 0.33234 (16) | 0.0251 (3) | |
N13 | 0.3089 (4) | 0.50008 (19) | 0.28236 (16) | 0.0347 (3) | |
H13C | 0.1758 | 0.4569 | 0.3347 | 0.042* | |
H13D | 0.3439 | 0.4868 | 0.1980 | 0.042* | |
N14 | 0.6746 (4) | 0.65059 (18) | 0.25175 (15) | 0.0326 (3) | |
H14C | 0.7771 | 0.7042 | 0.2840 | 0.039* | |
H14D | 0.7092 | 0.6373 | 0.1674 | 0.039* | |
O2A | 0.9294 (3) | 0.07978 (13) | −0.15308 (13) | 0.0283 (2) | |
O2B | 1.3220 (2) | 0.13899 (14) | −0.11107 (14) | 0.0295 (2) | |
C21 | 1.0806 (3) | 0.16165 (14) | −0.11120 (14) | 0.0207 (2) | |
C22 | 0.9677 (3) | 0.30346 (14) | −0.05506 (14) | 0.0208 (2) | |
H22 | 1.1041 | 0.3763 | −0.0891 | 0.025* | |
N21 | 0.7240 (3) | 0.34155 (14) | −0.10402 (14) | 0.0242 (2) | |
H21A | 0.7640 | 0.3423 | −0.1927 | 0.036* | |
H21B | 0.6675 | 0.4269 | −0.0762 | 0.036* | |
H21C | 0.5951 | 0.2782 | −0.0724 | 0.036* | |
C23 | 0.9130 (3) | 0.30002 (16) | 0.09677 (15) | 0.0247 (3) | |
H23A | 0.8522 | 0.3929 | 0.1277 | 0.030* | |
H23B | 1.0807 | 0.2816 | 0.1223 | 0.030* | |
C24 | 0.7064 (4) | 0.19070 (19) | 0.16861 (16) | 0.0280 (3) | |
H24A | 0.5341 | 0.2110 | 0.1486 | 0.034* | |
H24B | 0.7617 | 0.0972 | 0.1372 | 0.034* | |
C25 | 0.6789 (4) | 0.19318 (18) | 0.31791 (15) | 0.0265 (3) | |
H25A | 0.8431 | 0.1595 | 0.3395 | 0.032* | |
H25B | 0.6478 | 0.2892 | 0.3479 | 0.032* | |
N22 | 0.4547 (3) | 0.10299 (18) | 0.38483 (14) | 0.0324 (3) | |
H22A | 0.3686 | 0.0586 | 0.3364 | 0.039* | |
C26 | 0.3766 (3) | 0.08561 (17) | 0.51556 (16) | 0.0276 (3) | |
N23 | 0.5095 (3) | 0.14250 (19) | 0.59558 (16) | 0.0347 (3) | |
H23C | 0.6508 | 0.1924 | 0.5629 | 0.042* | |
H23D | 0.4549 | 0.1298 | 0.6805 | 0.042* | |
N24 | 0.1654 (4) | 0.0006 (2) | 0.56862 (18) | 0.0363 (3) | |
H24C | 0.1196 | −0.0155 | 0.6534 | 0.044* | |
H24D | 0.0765 | −0.0373 | 0.5177 | 0.044* | |
Cl1 | 0.11711 (9) | 0.89352 (5) | 0.25378 (5) | 0.04018 (12) | |
Cl2 | 0.94094 (10) | 0.38732 (5) | −0.41371 (5) | 0.04289 (13) |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1A | 0.0264 (5) | 0.0211 (5) | 0.0278 (5) | −0.0003 (4) | −0.0043 (4) | 0.0027 (4) |
O1B | 0.0195 (5) | 0.0330 (6) | 0.0334 (6) | −0.0059 (4) | −0.0030 (4) | 0.0019 (4) |
C11 | 0.0186 (5) | 0.0193 (5) | 0.0168 (5) | −0.0027 (4) | −0.0011 (4) | −0.0026 (4) |
C12 | 0.0210 (6) | 0.0168 (5) | 0.0214 (5) | −0.0026 (4) | −0.0037 (4) | 0.0000 (4) |
N11 | 0.0283 (6) | 0.0225 (5) | 0.0233 (5) | −0.0083 (4) | −0.0037 (5) | −0.0020 (4) |
C13 | 0.0282 (7) | 0.0339 (7) | 0.0172 (5) | −0.0087 (5) | −0.0011 (5) | −0.0008 (5) |
C14 | 0.0295 (7) | 0.0367 (8) | 0.0186 (6) | −0.0106 (6) | −0.0025 (5) | −0.0012 (5) |
N12 | 0.0345 (7) | 0.0425 (8) | 0.0179 (6) | −0.0135 (6) | −0.0028 (5) | −0.0022 (5) |
C15 | 0.0296 (7) | 0.0384 (8) | 0.0168 (6) | −0.0081 (6) | −0.0009 (5) | −0.0029 (5) |
C16 | 0.0266 (7) | 0.0281 (7) | 0.0199 (6) | −0.0003 (5) | −0.0040 (5) | −0.0010 (5) |
N13 | 0.0425 (9) | 0.0391 (8) | 0.0232 (6) | −0.0096 (6) | −0.0089 (6) | −0.0016 (5) |
N14 | 0.0357 (7) | 0.0390 (8) | 0.0195 (6) | −0.0055 (6) | 0.0009 (5) | −0.0009 (5) |
O2A | 0.0251 (5) | 0.0240 (5) | 0.0339 (6) | −0.0062 (4) | −0.0022 (4) | −0.0069 (4) |
O2B | 0.0203 (5) | 0.0300 (6) | 0.0372 (6) | 0.0016 (4) | −0.0041 (4) | −0.0048 (5) |
C21 | 0.0213 (6) | 0.0182 (5) | 0.0200 (5) | −0.0028 (4) | 0.0005 (4) | −0.0006 (4) |
C22 | 0.0206 (6) | 0.0178 (5) | 0.0221 (6) | −0.0022 (4) | −0.0009 (4) | −0.0017 (4) |
N21 | 0.0261 (6) | 0.0210 (5) | 0.0240 (6) | 0.0011 (4) | −0.0030 (4) | −0.0003 (4) |
C23 | 0.0253 (6) | 0.0263 (6) | 0.0213 (6) | −0.0031 (5) | −0.0029 (5) | −0.0050 (5) |
C24 | 0.0296 (7) | 0.0354 (8) | 0.0183 (6) | −0.0080 (6) | −0.0045 (5) | 0.0005 (5) |
C25 | 0.0305 (7) | 0.0302 (7) | 0.0171 (6) | −0.0030 (6) | −0.0021 (5) | −0.0002 (5) |
N22 | 0.0334 (7) | 0.0415 (8) | 0.0203 (6) | −0.0113 (6) | −0.0023 (5) | −0.0013 (5) |
C26 | 0.0283 (7) | 0.0284 (7) | 0.0234 (7) | −0.0020 (6) | −0.0004 (5) | −0.0001 (5) |
N23 | 0.0347 (8) | 0.0464 (9) | 0.0205 (6) | −0.0100 (6) | −0.0012 (5) | −0.0022 (5) |
N24 | 0.0350 (8) | 0.0404 (8) | 0.0295 (7) | −0.0109 (6) | 0.0008 (6) | 0.0001 (6) |
Cl1 | 0.0359 (2) | 0.0391 (2) | 0.0421 (2) | −0.00693 (16) | −0.00051 (17) | −0.01191 (17) |
Cl2 | 0.0486 (3) | 0.0438 (2) | 0.0326 (2) | −0.0183 (2) | −0.00280 (18) | 0.00565 (17) |
O1A—C11 | 1.2631 (18) | O2A—C21 | 1.2536 (18) |
O1B—C11 | 1.2477 (18) | O2B—C21 | 1.2555 (19) |
C11—C12 | 1.5359 (19) | C21—C22 | 1.5353 (19) |
C12—N11 | 1.4932 (19) | C22—N21 | 1.492 (2) |
C12—C13 | 1.525 (2) | C22—C23 | 1.525 (2) |
C13—C14 | 1.522 (2) | C23—C24 | 1.527 (2) |
C14—C15 | 1.523 (2) | C24—C25 | 1.515 (2) |
N12—C16 | 1.315 (2) | C25—N22 | 1.457 (2) |
N12—C15 | 1.454 (2) | N22—C26 | 1.319 (2) |
C16—N14 | 1.332 (2) | C26—N23 | 1.316 (2) |
C16—N13 | 1.343 (2) | C26—N24 | 1.349 (2) |
O1B—C11—O1A | 126.02 (14) | O2A—C21—O2B | 125.77 (14) |
O1B—C11—C12 | 117.37 (13) | O2A—C21—C22 | 118.67 (13) |
O1A—C11—C12 | 116.57 (12) | O2B—C21—C22 | 115.55 (13) |
N11—C12—C13 | 108.31 (12) | N21—C22—C23 | 112.22 (12) |
N11—C12—C11 | 109.70 (11) | N21—C22—C21 | 110.15 (12) |
C13—C12—C11 | 112.06 (11) | C23—C22—C21 | 111.07 (12) |
C14—C13—C12 | 111.90 (13) | C22—C23—C24 | 115.50 (12) |
C13—C14—C15 | 112.02 (14) | C25—C24—C23 | 110.48 (13) |
C16—N12—C15 | 124.93 (15) | N22—C25—C24 | 109.21 (14) |
N12—C15—C14 | 107.30 (14) | C26—N22—C25 | 123.65 (15) |
N12—C16—N14 | 121.49 (16) | N23—C26—N22 | 121.56 (16) |
N12—C16—N13 | 118.61 (15) | N23—C26—N24 | 118.86 (16) |
N14—C16—N13 | 119.85 (15) | N22—C26—N24 | 119.45 (17) |
O1B—C11—C12—N11 | 133.61 (14) | O2A—C21—C22—N21 | −20.19 (18) |
O1A—C11—C12—N11 | −48.54 (16) | O2B—C21—C22—N21 | 159.50 (13) |
O1B—C11—C12—C13 | −106.05 (16) | O2A—C21—C22—C23 | 104.77 (16) |
O1A—C11—C12—C13 | 71.80 (16) | O2B—C21—C22—C23 | −75.54 (16) |
N11—C12—C13—C14 | 172.10 (14) | N21—C22—C23—C24 | 62.31 (18) |
C11—C12—C13—C14 | 50.95 (18) | C21—C22—C23—C24 | −61.48 (18) |
C12—C13—C14—C15 | 166.95 (15) | C22—C23—C24—C25 | 177.49 (14) |
C16—N12—C15—C14 | 176.27 (18) | C23—C24—C25—N22 | 171.95 (15) |
C13—C14—C15—N12 | 176.72 (16) | C24—C25—N22—C26 | −178.56 (17) |
C15—N12—C16—N14 | −1.5 (3) | C25—N22—C26—N23 | −4.6 (3) |
C15—N12—C16—N13 | 175.79 (18) | C25—N22—C26—N24 | 179.52 (18) |
D—H···A | D—H | H···A | D···A | D—H···A |
N11—H11A···Cl1i | 0.89 | 2.35 | 3.213 (2) | 164 |
N11—H11B···O2Aii | 0.89 | 2.05 | 2.907 (2) | 161 |
N11—H11C···O1Biii | 0.89 | 2.05 | 2.932 (2) | 172 |
N12—H12A···Cl2iv | 0.86 | 2.35 | 3.166 (2) | 159 |
N13—H13C···Cl2iv | 0.86 | 2.66 | 3.401 (2) | 146 |
N13—H13D···O1Av | 0.86 | 2.04 | 2.805 (2) | 148 |
N14—H14C···Cl1iii | 0.86 | 2.47 | 3.240 (2) | 150 |
N14—H14D···O1Bvi | 0.86 | 2.18 | 2.942 (2) | 147 |
N21—H21A···Cl2 | 0.89 | 2.28 | 3.145 (2) | 166 |
N21—H21B···O1Av | 0.89 | 2.04 | 2.876 (2) | 156 |
N21—H21C···O2Bvii | 0.89 | 2.04 | 2.835 (2) | 148 |
N22—H22A···Cl1viii | 0.86 | 2.33 | 3.171 (2) | 164 |
N23—H23C···Cl2i | 0.86 | 2.43 | 3.193 (2) | 149 |
N23—H23D···O2Biv | 0.86 | 2.10 | 2.953 (2) | 170 |
N24—H24C···O2Aiv | 0.86 | 2.22 | 2.963 (2) | 144 |
N24—H24D···Cl1viii | 0.86 | 2.78 | 3.499 (2) | 142 |
Symmetry codes: (i) x, y, z+1; (ii) x, y+1, z+1; (iii) x+1, y, z; (iv) x−1, y, z+1; (v) x, y, z−1; (vi) x+1, y, z−1; (vii) x−1, y, z; (viii) x, y−1, z. |