Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805033131/bh6029sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536805033131/bh6029Isup2.hkl |
CCDC reference: 289639
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.002 Å
- R factor = 0.029
- wR factor = 0.079
- Data-to-parameter ratio = 14.6
checkCIF/PLATON results
No syntax errors found
Alert level C PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ? PLAT199_ALERT_1_C Check the Reported _cell_measurement_temperature 293 K PLAT200_ALERT_1_C Check the Reported _diffrn_ambient_temperature . 293 K PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........ 3 PLAT731_ALERT_1_C Bond Calc 0.83(3), Rep 0.833(10) ...... 3.00 su-Rat OW -HW1 1.555 1.555 PLAT735_ALERT_1_C D-H Calc 0.83(3), Rep 0.833(10) ...... 3.00 su-Rat O1# -H1# 1.555 1.555 PLAT736_ALERT_1_C H...A Calc 2.35(3), Rep 2.350(14) ...... 2.14 su-Rat H1# -CL1 1.555 2.645
Alert level G REFLT03_ALERT_4_G WARNING: Large fraction of Friedel related reflns may be needed to determine absolute structure From the CIF: _diffrn_reflns_theta_max 30.00 From the CIF: _reflns_number_total 2136 Count of symmetry unique reflns 1858 Completeness (_total/calc) 114.96% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 278 Fraction of Friedel pairs measured 0.150 Are heavy atom types Z>Si present yes
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 7 ALERT level C = Check and explain 1 ALERT level G = General alerts; check 6 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 0 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 2 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: R3m/V (Siemens, 1989); cell refinement: R3m/V; data reduction: XDISK (Siemens, 1989); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL-Plus (Sheldrick, 1998); software used to prepare material for publication: SHELXL97.
C9H13N2O2+·Cl−·H2O | F(000) = 248 |
Mr = 234.68 | Dx = 1.332 Mg m−3 |
Monoclinic, P21 | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: P 2yb | Cell parameters from 23 reflections |
a = 7.3671 (17) Å | θ = 7.5–12.5° |
b = 6.020 (2) Å | µ = 0.32 mm−1 |
c = 13.689 (3) Å | T = 293 K |
β = 105.551 (12)° | Block, colourless |
V = 584.9 (3) Å3 | 0.59 × 0.46 × 0.43 mm |
Z = 2 |
Siemens P4 four-circle diffractometer | 1966 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.047 |
Graphite monochromator | θmax = 30.0°, θmin = 3.7° |
Profile fitted ω scans | h = −1→10 |
Absorption correction: ψ scan (SHELXTL-Plus; Sheldrick, 1998) | k = −8→8 |
Tmin = 0.790, Tmax = 0.875 | l = −19→18 |
2595 measured reflections | 3 standard reflections every 100 reflections |
2136 independent reflections | intensity decay: 1% |
Refinement on F2 | Hydrogen site location: inferred from neighbouring sites |
Least-squares matrix: full | H atoms treated by a mixture of independent and constrained refinement |
R[F2 > 2σ(F2)] = 0.029 | w = 1/[σ2(Fo2) + (0.0422P)2 + 0.0448P] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.079 | (Δ/σ)max = 0.003 |
S = 1.04 | Δρmax = 0.23 e Å−3 |
2136 reflections | Δρmin = −0.20 e Å−3 |
146 parameters | Extinction correction: SHELXL97 (Sheldrick, 1997), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
3 restraints | Extinction coefficient: 0.150 (11) |
Primary atom site location: structure-invariant direct methods | Absolute structure: Flack (1983), with 293 Friedel pairs |
Secondary atom site location: difference Fourier map | Absolute structure parameter: −0.04 (6) |
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 | ||
Cl1 | 0.17138 (6) | 0.97493 (8) | 0.15281 (3) | 0.04233 (13) | |
C1 | 0.7308 (2) | 0.3821 (3) | 0.16898 (11) | 0.0369 (4) | |
O1 | 0.6515 (2) | 0.2432 (3) | 0.10703 (13) | 0.0660 (5) | |
N1 | 0.9148 (2) | 0.3822 (3) | 0.21385 (12) | 0.0451 (4) | |
H1 | 0.9855 | 0.2801 | 0.1998 | 0.054* | |
H11 | 0.9631 | 0.4842 | 0.2569 | 0.054* | |
C2 | 0.6153 (2) | 0.5671 (3) | 0.19985 (11) | 0.0333 (3) | |
H2 | 0.6987 | 0.6865 | 0.2342 | 0.040* | |
N2 | 0.4848 (2) | 0.6523 (3) | 0.10422 (11) | 0.0404 (4) | |
H21 | 0.5515 | 0.7120 | 0.0655 | 0.048* | |
H22 | 0.4094 | 0.7549 | 0.1190 | 0.048* | |
H23 | 0.4158 | 0.5406 | 0.0711 | 0.048* | |
C3 | 0.4984 (2) | 0.4776 (4) | 0.26913 (11) | 0.0399 (3) | |
H31 | 0.4045 | 0.5874 | 0.2735 | 0.048* | |
H32 | 0.4325 | 0.3445 | 0.2390 | 0.048* | |
C11 | 0.6174 (2) | 0.4236 (3) | 0.37527 (11) | 0.0351 (4) | |
C12 | 0.7114 (3) | 0.2220 (4) | 0.39778 (13) | 0.0405 (4) | |
H12 | 0.7015 | 0.1174 | 0.3466 | 0.049* | |
C13 | 0.8198 (3) | 0.1738 (3) | 0.49542 (14) | 0.0394 (4) | |
H13 | 0.8827 | 0.0387 | 0.5093 | 0.047* | |
C14 | 0.8332 (2) | 0.3282 (3) | 0.57149 (12) | 0.0359 (4) | |
O4 | 0.9428 (2) | 0.2751 (3) | 0.66704 (9) | 0.0536 (4) | |
H4 | 0.9406 | 0.3779 | 0.7060 | 0.080* | |
C15 | 0.7414 (2) | 0.5304 (3) | 0.55156 (12) | 0.0374 (4) | |
H15 | 0.7512 | 0.6339 | 0.6031 | 0.045* | |
C16 | 0.6339 (2) | 0.5771 (3) | 0.45320 (12) | 0.0364 (3) | |
H16 | 0.5723 | 0.7130 | 0.4395 | 0.044* | |
OW | 0.7644 (2) | 0.8168 (3) | 0.00989 (11) | 0.0507 (4) | |
HW1 | 0.804 (4) | 0.736 (6) | −0.029 (2) | 0.091 (11)* | |
HW2 | 0.862 (3) | 0.867 (5) | 0.0496 (17) | 0.063 (8)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Cl1 | 0.0431 (2) | 0.0426 (2) | 0.04370 (19) | 0.0094 (2) | 0.01584 (14) | 0.0028 (2) |
C1 | 0.0370 (7) | 0.0413 (9) | 0.0290 (6) | 0.0089 (8) | 0.0028 (5) | −0.0048 (7) |
O1 | 0.0543 (8) | 0.0669 (11) | 0.0617 (9) | 0.0188 (8) | −0.0106 (7) | −0.0369 (9) |
N1 | 0.0360 (7) | 0.0491 (9) | 0.0462 (7) | 0.0112 (7) | 0.0043 (6) | −0.0114 (8) |
C2 | 0.0327 (6) | 0.0376 (8) | 0.0273 (6) | 0.0065 (7) | 0.0041 (5) | −0.0035 (6) |
N2 | 0.0424 (7) | 0.0477 (9) | 0.0299 (6) | 0.0152 (7) | 0.0079 (5) | 0.0029 (6) |
C3 | 0.0349 (6) | 0.0514 (10) | 0.0318 (6) | 0.0058 (10) | 0.0059 (5) | 0.0012 (9) |
C11 | 0.0345 (7) | 0.0402 (10) | 0.0313 (6) | 0.0039 (7) | 0.0101 (5) | 0.0031 (6) |
C12 | 0.0519 (10) | 0.0358 (9) | 0.0362 (7) | 0.0053 (8) | 0.0159 (7) | −0.0022 (8) |
C13 | 0.0451 (9) | 0.0351 (9) | 0.0413 (8) | 0.0105 (8) | 0.0174 (7) | 0.0065 (7) |
C14 | 0.0332 (7) | 0.0431 (9) | 0.0328 (7) | 0.0053 (7) | 0.0111 (6) | 0.0068 (7) |
O4 | 0.0613 (8) | 0.0628 (11) | 0.0333 (6) | 0.0229 (8) | 0.0068 (5) | 0.0083 (7) |
C15 | 0.0411 (8) | 0.0380 (9) | 0.0334 (7) | 0.0045 (7) | 0.0103 (6) | −0.0025 (7) |
C16 | 0.0378 (7) | 0.0342 (8) | 0.0369 (7) | 0.0075 (7) | 0.0095 (6) | 0.0032 (7) |
OW | 0.0448 (7) | 0.0572 (9) | 0.0468 (7) | −0.0018 (7) | 0.0068 (6) | −0.0149 (7) |
C1—O1 | 1.222 (2) | C11—C12 | 1.390 (3) |
C1—N1 | 1.330 (2) | C11—C16 | 1.392 (2) |
C1—C2 | 1.529 (2) | C12—C13 | 1.392 (3) |
N1—H1 | 0.8600 | C12—H12 | 0.9300 |
N1—H11 | 0.8600 | C13—C14 | 1.380 (3) |
C2—N2 | 1.492 (2) | C13—H13 | 0.9300 |
C2—C3 | 1.540 (2) | C14—O4 | 1.378 (2) |
C2—H2 | 0.9800 | C14—C15 | 1.383 (3) |
N2—H21 | 0.8900 | O4—H4 | 0.8200 |
N2—H22 | 0.8900 | C15—C16 | 1.396 (2) |
N2—H23 | 0.8900 | C15—H15 | 0.9300 |
C3—C11 | 1.518 (2) | C16—H16 | 0.9300 |
C3—H31 | 0.9700 | OW—HW1 | 0.833 (10) |
C3—H32 | 0.9700 | OW—HW2 | 0.830 (10) |
O1—C1—N1 | 123.99 (18) | C2—C3—H32 | 109.0 |
O1—C1—C2 | 119.50 (15) | H31—C3—H32 | 107.8 |
N1—C1—C2 | 116.50 (16) | C12—C11—C16 | 118.29 (15) |
C1—N1—H1 | 120.0 | C12—C11—C3 | 121.66 (17) |
C1—N1—H11 | 120.0 | C16—C11—C3 | 120.05 (18) |
H1—N1—H11 | 120.0 | C11—C12—C13 | 121.22 (17) |
N2—C2—C1 | 106.46 (12) | C11—C12—H12 | 119.4 |
N2—C2—C3 | 108.99 (13) | C13—C12—H12 | 119.4 |
C1—C2—C3 | 111.11 (17) | C14—C13—C12 | 119.41 (18) |
N2—C2—H2 | 110.1 | C14—C13—H13 | 120.3 |
C1—C2—H2 | 110.1 | C12—C13—H13 | 120.3 |
C3—C2—H2 | 110.1 | O4—C14—C13 | 117.73 (18) |
C2—N2—H21 | 109.5 | O4—C14—C15 | 121.49 (17) |
C2—N2—H22 | 109.5 | C13—C14—C15 | 120.77 (15) |
H21—N2—H22 | 109.5 | C14—O4—H4 | 109.5 |
C2—N2—H23 | 109.5 | C14—C15—C16 | 119.25 (16) |
H21—N2—H23 | 109.5 | C14—C15—H15 | 120.4 |
H22—N2—H23 | 109.5 | C16—C15—H15 | 120.4 |
C11—C3—C2 | 112.92 (13) | C11—C16—C15 | 121.06 (17) |
C11—C3—H31 | 109.0 | C11—C16—H16 | 119.5 |
C2—C3—H31 | 109.0 | C15—C16—H16 | 119.5 |
C11—C3—H32 | 109.0 | HW1—OW—HW2 | 104 (3) |
D—H···A | D—H | H···A | D···A | D—H···A |
O4—H4···Cl1i | 0.82 | 2.37 | 3.0576 (16) | 142 |
N1—H11···O4ii | 0.86 | 2.06 | 2.905 (3) | 167 |
N2—H22···Cl1 | 0.89 | 2.34 | 3.2206 (17) | 170 |
N2—H21···OW | 0.89 | 2.02 | 2.884 (2) | 164 |
N2—H23···OWiii | 0.89 | 2.00 | 2.890 (3) | 173 |
OW—HW1···Cl1iii | 0.83 (1) | 2.35 (1) | 3.1601 (17) | 164 (3) |
OW—HW2···Cl1iv | 0.83 (1) | 2.43 (1) | 3.2523 (16) | 171 (3) |
Symmetry codes: (i) −x+1, y−1/2, −z+1; (ii) −x+2, y+1/2, −z+1; (iii) −x+1, y−1/2, −z; (iv) x+1, y, z. |
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