Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S160053680604387X/gk2029sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S160053680604387X/gk2029Isup2.hkl |
CCDC reference: 627669
Key indicators
- Single-crystal X-ray study
- T = 173 K
- Mean (C-C) = 0.002 Å
- R factor = 0.031
- wR factor = 0.089
- Data-to-parameter ratio = 13.1
checkCIF/PLATON results
No syntax errors found
Alert level B PLAT222_ALERT_3_B Large Non-Solvent H Ueq(max)/Ueq(min) ... 4.33 Ratio PLAT417_ALERT_2_B Short Inter D-H..H-D H10 .. H14B .. 2.09 Ang.
Alert level C PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd. # 2 H2 O
0 ALERT level A = In general: serious problem 2 ALERT level B = Potentially serious problem 1 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 1 ALERT type 2 Indicator that the structure model may be wrong or deficient 1 ALERT type 3 Indicator that the structure quality may be low 1 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check
Data collection: SMART (Bruker, 1999); cell refinement: SMART; data reduction: SAINT (Bruker 2006); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997a); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997a); molecular graphics: SHELXTL (Sheldrick, 2000); software used to prepare material for publication: SHELXTL.
C9H12NO3+·H2O·Cl− | F(000) = 496 |
Mr = 235.66 | Dx = 1.405 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2yn | Cell parameters from 5283 reflections |
a = 4.1838 (5) Å | θ = 2.3–28.3° |
b = 17.608 (2) Å | µ = 0.34 mm−1 |
c = 15.181 (2) Å | T = 173 K |
β = 94.959 (2)° | Irregular, colourless |
V = 1114.2 (2) Å3 | 0.50 × 0.45 × 0.40 mm |
Z = 4 |
Bruker SMART1000/P4 diffractometer | 2507 independent reflections |
Radiation source: fine-focus sealed tube, Siemens Kristalloflex 760 | 2246 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.023 |
φ and ω scans | θmax = 27.5°, θmin = 1.8° |
Absorption correction: multi-scan SADABS (Sheldrick, 1997b) | h = −5→5 |
Tmin = 0.777, Tmax = 0.874 | k = −21→22 |
7627 measured reflections | l = −17→19 |
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)] = 0.031 | Hydrogen site location: difference Fourier map |
wR(F2) = 0.089 | All H-atom parameters refined |
S = 1.05 | w = 1/[σ2(Fo2) + (0.0523P)2 + 0.2706P] where P = (Fo2 + 2Fc2)/3 |
2507 reflections | (Δ/σ)max = 0.001 |
192 parameters | Δρmax = 0.39 e Å−3 |
0 restraints | Δρmin = −0.15 e Å−3 |
Experimental. NMR data for (I) 1H NMR (DMSO-d6, δ, p.p.m.): 8.25 (s, 1H), 6.47 (s, 1H), 5.09 (s, 2H), 3.38 (s, 3H), 2.58 (s, 3H); 13C (DMSO-d6, δ, p.p.m.): 145.5, 139.9, 134.9, 134.1, 121.8, 66.3, 52.0, 11.1. Crystal decay was monitored by repeating the initial 50 frames at the end of the data collection and analyzing duplicate reflections. |
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 | ||
C1 | 0.3798 (3) | 0.81018 (7) | 0.52322 (8) | 0.0261 (2) | |
C2 | 0.2717 (3) | 0.77179 (7) | 0.59499 (7) | 0.0235 (2) | |
C3 | 0.3188 (3) | 0.80086 (7) | 0.68001 (8) | 0.0254 (2) | |
C4 | 0.4860 (3) | 0.86997 (7) | 0.69095 (8) | 0.0271 (3) | |
N5 | 0.5883 (3) | 0.90377 (6) | 0.61909 (7) | 0.0278 (2) | |
C6 | 0.5418 (3) | 0.87739 (7) | 0.53574 (8) | 0.0288 (3) | |
C7 | 0.2880 (4) | 0.76541 (8) | 0.44106 (8) | 0.0332 (3) | |
O8 | 0.0779 (2) | 0.70700 (6) | 0.46971 (6) | 0.0358 (2) | |
C9 | 0.1273 (3) | 0.69745 (7) | 0.56252 (8) | 0.0264 (2) | |
O10 | 0.2182 (3) | 0.76942 (6) | 0.75289 (6) | 0.0364 (2) | |
C11 | 0.5555 (4) | 0.90702 (9) | 0.77866 (10) | 0.0395 (3) | |
C13 | 0.2439 (4) | 0.56686 (8) | 0.56719 (13) | 0.0444 (4) | |
O12 | 0.3588 (2) | 0.64170 (5) | 0.58689 (6) | 0.0308 (2) | |
Cl1 | 1.01855 (7) | 1.044772 (17) | 0.64238 (2) | 0.03245 (12) | |
O14 | 1.5376 (3) | 1.13525 (6) | 0.75461 (7) | 0.0375 (2) | |
H5 | 0.697 (4) | 0.9466 (9) | 0.6255 (11) | 0.035 (4)* | |
H6 | 0.623 (4) | 0.9054 (9) | 0.4920 (10) | 0.032 (4)* | |
H7A | 0.166 (4) | 0.7952 (10) | 0.3948 (11) | 0.039 (4)* | |
H7B | 0.487 (4) | 0.7435 (9) | 0.4206 (11) | 0.041 (4)* | |
H9 | −0.078 (3) | 0.6853 (8) | 0.5853 (9) | 0.024 (3)* | |
H10 | 0.122 (5) | 0.7254 (12) | 0.7427 (13) | 0.053 (5)* | |
H11A | 0.649 (6) | 0.9530 (14) | 0.7766 (15) | 0.072 (7)* | |
H11B | 0.684 (7) | 0.8782 (17) | 0.8149 (19) | 0.104 (9)* | |
H11C | 0.372 (7) | 0.9163 (16) | 0.8073 (18) | 0.099 (9)* | |
H13A | 0.214 (5) | 0.5580 (12) | 0.5025 (15) | 0.065 (6)* | |
H13B | 0.398 (5) | 0.5303 (12) | 0.5966 (13) | 0.058 (6)* | |
H13C | 0.054 (5) | 0.5584 (10) | 0.5950 (13) | 0.050 (5)* | |
H14A | 1.689 (6) | 1.1207 (13) | 0.7344 (15) | 0.065 (6)* | |
H14B | 1.392 (6) | 1.1100 (13) | 0.7268 (14) | 0.064 (6)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.0280 (5) | 0.0262 (6) | 0.0243 (6) | 0.0031 (5) | 0.0035 (4) | 0.0023 (4) |
C2 | 0.0227 (5) | 0.0226 (5) | 0.0252 (6) | 0.0022 (4) | 0.0021 (4) | 0.0022 (4) |
C3 | 0.0277 (5) | 0.0245 (6) | 0.0242 (6) | 0.0020 (5) | 0.0031 (4) | 0.0027 (4) |
C4 | 0.0309 (6) | 0.0239 (6) | 0.0263 (6) | 0.0029 (5) | 0.0016 (5) | −0.0002 (4) |
N5 | 0.0297 (5) | 0.0208 (5) | 0.0329 (5) | −0.0001 (4) | 0.0030 (4) | 0.0018 (4) |
C6 | 0.0321 (6) | 0.0267 (6) | 0.0284 (6) | 0.0014 (5) | 0.0069 (5) | 0.0055 (5) |
C7 | 0.0420 (7) | 0.0342 (7) | 0.0238 (6) | −0.0034 (6) | 0.0041 (5) | 0.0007 (5) |
O8 | 0.0427 (5) | 0.0382 (5) | 0.0257 (5) | −0.0099 (4) | −0.0014 (4) | −0.0013 (4) |
C9 | 0.0267 (5) | 0.0268 (6) | 0.0257 (6) | −0.0016 (5) | 0.0016 (4) | −0.0003 (5) |
O10 | 0.0514 (6) | 0.0348 (5) | 0.0238 (4) | −0.0094 (4) | 0.0079 (4) | 0.0020 (4) |
C11 | 0.0559 (9) | 0.0322 (7) | 0.0298 (7) | −0.0063 (7) | 0.0008 (6) | −0.0060 (6) |
C13 | 0.0501 (9) | 0.0245 (7) | 0.0599 (10) | −0.0042 (6) | 0.0112 (8) | −0.0045 (7) |
O12 | 0.0287 (4) | 0.0222 (4) | 0.0417 (5) | −0.0001 (3) | 0.0045 (4) | −0.0002 (4) |
Cl1 | 0.03036 (18) | 0.02765 (18) | 0.0402 (2) | −0.00338 (11) | 0.00772 (13) | −0.00397 (12) |
O14 | 0.0332 (5) | 0.0388 (6) | 0.0414 (6) | 0.0028 (4) | 0.0076 (4) | −0.0121 (4) |
C1—C6 | 1.3689 (18) | C7—H7B | 0.993 (18) |
C1—C2 | 1.3906 (16) | O8—C9 | 1.4164 (15) |
C1—C7 | 1.4973 (18) | C9—O12 | 1.4058 (15) |
C2—C3 | 1.3865 (16) | C9—H9 | 0.977 (15) |
C2—C9 | 1.5065 (17) | O10—H10 | 0.88 (2) |
C3—O10 | 1.3374 (14) | C11—H11A | 0.90 (2) |
C3—C4 | 1.4062 (17) | C11—H11B | 0.89 (3) |
C4—N5 | 1.3447 (16) | C11—H11C | 0.93 (3) |
C4—C11 | 1.4886 (18) | C13—O12 | 1.4254 (17) |
N5—C6 | 1.3461 (17) | C13—H13A | 0.99 (2) |
N5—H5 | 0.883 (17) | C13—H13B | 0.99 (2) |
C6—H6 | 0.916 (16) | C13—H13C | 0.94 (2) |
C7—O8 | 1.4442 (16) | O14—H14A | 0.77 (3) |
C7—H7A | 0.983 (17) | O14—H14B | 0.84 (2) |
C6—C1—C2 | 120.15 (11) | H7A—C7—H7B | 112.4 (13) |
C6—C1—C7 | 131.23 (11) | C9—O8—C7 | 110.10 (9) |
C2—C1—C7 | 108.62 (11) | O12—C9—O8 | 112.50 (10) |
C3—C2—C1 | 121.33 (11) | O12—C9—C2 | 105.85 (9) |
C3—C2—C9 | 130.24 (10) | O8—C9—C2 | 104.02 (10) |
C1—C2—C9 | 108.32 (10) | O12—C9—H9 | 111.1 (8) |
O10—C3—C2 | 125.99 (11) | O8—C9—H9 | 108.7 (8) |
O10—C3—C4 | 116.70 (11) | C2—C9—H9 | 114.5 (8) |
C2—C3—C4 | 117.31 (10) | C3—O10—H10 | 113.0 (12) |
N5—C4—C3 | 118.49 (11) | C4—C11—H11A | 114.5 (15) |
N5—C4—C11 | 118.71 (12) | C4—C11—H11B | 111.3 (18) |
C3—C4—C11 | 122.80 (12) | H11A—C11—H11B | 107 (2) |
C4—N5—C6 | 125.42 (11) | C4—C11—H11C | 113.0 (17) |
C4—N5—H5 | 119.1 (11) | H11A—C11—H11C | 104 (2) |
C6—N5—H5 | 115.5 (11) | H11B—C11—H11C | 107 (2) |
N5—C6—C1 | 117.28 (11) | O12—C13—H13A | 111.4 (12) |
N5—C6—H6 | 117.6 (10) | O12—C13—H13B | 108.2 (12) |
C1—C6—H6 | 125.2 (10) | H13A—C13—H13B | 111.6 (17) |
O8—C7—C1 | 104.07 (10) | O12—C13—H13C | 109.5 (11) |
O8—C7—H7A | 107.6 (10) | H13A—C13—H13C | 112.2 (17) |
C1—C7—H7A | 113.2 (10) | H13B—C13—H13C | 103.7 (16) |
O8—C7—H7B | 111.6 (10) | C9—O12—C13 | 112.24 (11) |
C1—C7—H7B | 107.6 (10) | H14A—O14—H14B | 102 (2) |
C1—C2—C9—O8 | −16.32 (13) | O8—C7—C1—C2 | 9.20 (14) |
C2—C9—O8—C7 | 22.65 (13) | C7—C1—C2—C9 | 4.26 (14) |
C9—O8—C7—C1 | −20.23 (14) |
D—H···A | D—H | H···A | D···A | D—H···A |
N5—H5···Cl1 | 0.883 (17) | 2.191 (17) | 3.0692 (12) | 173.4 (15) |
O10—H10···O14i | 0.88 (2) | 1.72 (2) | 2.5920 (15) | 168.0 (19) |
O14—H14A···Cl1ii | 0.77 (3) | 2.44 (2) | 3.1753 (11) | 159 (2) |
O14—H14B···Cl1 | 0.84 (2) | 2.25 (2) | 3.0849 (12) | 175.5 (19) |
Symmetry codes: (i) −x+3/2, y−1/2, −z+3/2; (ii) x+1, y, z. |
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