Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805012523/bt6652sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536805012523/bt6652Isup2.hkl |
CCDC reference: 271826
Key indicators
- Single-crystal X-ray study
- T = 566 K
- Mean (C-C) = 0.005 Å
- R factor = 0.060
- wR factor = 0.152
- Data-to-parameter ratio = 11.6
checkCIF/PLATON results
No syntax errors found
Alert level C PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ? PLAT152_ALERT_1_C Supplied and Calc Volume s.u. Inconsistent ..... ? PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor .... 2.26 PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 5 PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ...... 0.00 Deg. O3' -C3' -O3' 1.555 1.555 1.555 PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ...... 0.00 Deg. O3' -O3' -C3' 1.555 1.555 1.555
Alert level G HYDTR01_ALERT_1_G Extra text has been found in the _refine_ls_hydrogen_treatment fie Explanatory text should be in the _publ_section_refinement field. Hydrogen treatment given as constr. Hydrogen treatment identified as constr
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 6 ALERT level C = Check and explain 1 ALERT level G = General alerts; check 3 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 3 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 0 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: Siemens R3m/V User's Guide (Siemens, 1989); cell refinement: Siemens R3m/V User's Guide; 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, 1995); software used to prepare material for publication: SHELXL97.
2C9H8NO+·C4O42− | F(000) = 840 |
Mr = 404.37 | Dx = 1.502 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 15 reflections |
a = 9.578 (3) Å | θ = 7.5–15° |
b = 7.3024 (17) Å | µ = 0.11 mm−1 |
c = 25.656 (5) Å | T = 566 K |
β = 94.830 (13)° | Prism, yellow |
V = 1788.1 (6) Å3 | 0.42 × 0.36 × 0.28 mm |
Z = 4 |
Siemens P4 four-circle diffractometer | 1640 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.047 |
Graphite monochromator | θmax = 25.0°, θmin = 2.1° |
Profile–fitted scans | h = −1→11 |
Absorption correction: psi-scan (XPREP in SHELXTL-Plus; Sheldrick, 1995) | k = −1→8 |
Tmin = 0.930, Tmax = 0.973 | l = −30→30 |
4380 measured reflections | 3 standard reflections every 100 reflections |
3152 independent reflections | intensity decay: 2% |
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)] = 0.060 | Constrained. |
wR(F2) = 0.152 | w = 1/[σ2(Fo2) + (0.0609P)2] where P = (Fo2 + 2Fc2)/3 |
S = 0.99 | (Δ/σ)max < 0.001 |
3152 reflections | Δρmax = 0.23 e Å−3 |
272 parameters | Δρmin = −0.21 e Å−3 |
0 restraints | Extinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.0063 (13) |
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 | ||
N1 | 0.6813 (3) | 0.8221 (4) | 0.14085 (10) | 0.0388 (8) | |
H1 | 0.6166 | 0.8537 | 0.1173 | 0.047* | |
C2 | 0.6607 (4) | 0.8465 (5) | 0.19036 (13) | 0.0479 (10) | |
H2 | 0.5770 | 0.8981 | 0.1991 | 0.057* | |
C3 | 0.7618 (4) | 0.7966 (6) | 0.22986 (13) | 0.0486 (10) | |
H3 | 0.7457 | 0.8151 | 0.2647 | 0.058* | |
C4 | 0.8843 (4) | 0.7206 (5) | 0.21728 (14) | 0.0458 (10) | |
H4 | 0.9525 | 0.6875 | 0.2435 | 0.055* | |
C5 | 1.0310 (4) | 0.6133 (5) | 0.14795 (14) | 0.0463 (10) | |
H5 | 1.1008 | 0.5742 | 0.1728 | 0.056* | |
C6 | 1.0485 (4) | 0.5941 (5) | 0.09651 (14) | 0.0493 (10) | |
H6 | 1.1307 | 0.5425 | 0.0863 | 0.059* | |
C7 | 0.9437 (4) | 0.6515 (5) | 0.05810 (14) | 0.0455 (10) | |
H7 | 0.9583 | 0.6377 | 0.0229 | 0.055* | |
C8 | 0.8203 (3) | 0.7273 (5) | 0.07148 (13) | 0.0342 (9) | |
O8 | 0.7147 (2) | 0.7835 (4) | 0.03719 (9) | 0.0464 (7) | |
H8 | 0.7437 | 0.7963 | 0.0082 | 0.060* | |
C9 | 0.8024 (4) | 0.7480 (5) | 0.12567 (13) | 0.0320 (8) | |
C10 | 0.9077 (4) | 0.6921 (5) | 0.16403 (13) | 0.0375 (9) | |
N11 | 0.1840 (3) | 0.7290 (4) | 0.39237 (10) | 0.0367 (8) | |
H11 | 0.1192 | 0.7070 | 0.3679 | 0.044* | |
C12 | 0.1606 (4) | 0.6914 (5) | 0.44123 (13) | 0.0443 (10) | |
H12 | 0.0740 | 0.6443 | 0.4484 | 0.053* | |
C13 | 0.2623 (4) | 0.7207 (6) | 0.48181 (14) | 0.0495 (11) | |
H13 | 0.2446 | 0.6931 | 0.5160 | 0.059* | |
C14 | 0.3882 (4) | 0.7902 (5) | 0.47132 (13) | 0.0441 (10) | |
H14 | 0.4581 | 0.8061 | 0.4984 | 0.053* | |
C15 | 0.5403 (3) | 0.9195 (5) | 0.40691 (14) | 0.0463 (10) | |
H15 | 0.6110 | 0.9449 | 0.4330 | 0.056* | |
C16 | 0.5583 (4) | 0.9605 (6) | 0.35596 (14) | 0.0516 (11) | |
H16 | 0.6407 | 1.0170 | 0.3477 | 0.062* | |
C17 | 0.4544 (4) | 0.9188 (5) | 0.31586 (14) | 0.0467 (10) | |
H17 | 0.4704 | 0.9451 | 0.2814 | 0.056* | |
C18 | 0.3299 (4) | 0.8402 (5) | 0.32634 (12) | 0.0368 (9) | |
O18 | 0.2241 (2) | 0.7962 (4) | 0.29006 (9) | 0.0466 (7) | |
H18 | 0.2455 | 0.8259 | 0.2609 | 0.056* | |
C19 | 0.3086 (3) | 0.8020 (5) | 0.37935 (12) | 0.0309 (8) | |
C20 | 0.4141 (3) | 0.8385 (5) | 0.41982 (13) | 0.0370 (9) | |
C1' | 0.2130 (3) | 1.0903 (5) | 0.09176 (12) | 0.0361 (9) | |
O1' | 0.1701 (2) | 1.1717 (4) | 0.04998 (8) | 0.0500 (7) | |
C2' | 0.3375 (3) | 0.9830 (5) | 0.10938 (12) | 0.0368 (9) | |
O2' | 0.4466 (2) | 0.9394 (4) | 0.08811 (8) | 0.0497 (7) | |
C3' | 0.2803 (3) | 0.9535 (5) | 0.15989 (12) | 0.0381 (9) | |
O3' | 0.3223 (2) | 0.8681 (4) | 0.20064 (8) | 0.0522 (8) | |
C4' | 0.1560 (3) | 1.0622 (5) | 0.14257 (12) | 0.0353 (8) | |
O4' | 0.0474 (2) | 1.1076 (4) | 0.16304 (8) | 0.0473 (7) |
U11 | U22 | U33 | U12 | U13 | U23 | |
N1 | 0.0371 (18) | 0.050 (2) | 0.0287 (16) | 0.0048 (16) | 0.0014 (13) | 0.0056 (14) |
C2 | 0.046 (2) | 0.063 (3) | 0.036 (2) | 0.011 (2) | 0.0102 (17) | 0.002 (2) |
C3 | 0.056 (3) | 0.067 (3) | 0.0231 (19) | 0.002 (2) | 0.0012 (18) | −0.0030 (19) |
C4 | 0.044 (2) | 0.058 (3) | 0.033 (2) | 0.000 (2) | −0.0091 (18) | 0.0041 (19) |
C5 | 0.036 (2) | 0.058 (3) | 0.044 (2) | 0.006 (2) | −0.0020 (17) | 0.005 (2) |
C6 | 0.040 (2) | 0.058 (3) | 0.051 (2) | 0.009 (2) | 0.0081 (18) | 0.003 (2) |
C7 | 0.048 (2) | 0.053 (3) | 0.037 (2) | 0.008 (2) | 0.0075 (17) | −0.0011 (19) |
C8 | 0.032 (2) | 0.039 (2) | 0.0306 (18) | 0.0024 (17) | −0.0002 (16) | 0.0056 (16) |
O8 | 0.0386 (15) | 0.0716 (19) | 0.0288 (13) | 0.0089 (14) | 0.0018 (11) | 0.0081 (12) |
C9 | 0.034 (2) | 0.031 (2) | 0.031 (2) | −0.0030 (16) | 0.0026 (16) | 0.0041 (15) |
C10 | 0.036 (2) | 0.041 (2) | 0.036 (2) | −0.0058 (18) | −0.0002 (16) | 0.0019 (17) |
N11 | 0.0314 (17) | 0.0460 (19) | 0.0320 (17) | −0.0038 (15) | −0.0013 (13) | −0.0009 (14) |
C12 | 0.042 (2) | 0.053 (3) | 0.038 (2) | −0.003 (2) | 0.0097 (18) | 0.0043 (19) |
C13 | 0.052 (3) | 0.065 (3) | 0.032 (2) | −0.005 (2) | 0.0049 (19) | 0.0086 (19) |
C14 | 0.046 (2) | 0.056 (3) | 0.0289 (19) | 0.004 (2) | −0.0087 (17) | 0.0043 (18) |
C15 | 0.034 (2) | 0.059 (3) | 0.045 (2) | −0.006 (2) | −0.0040 (17) | −0.007 (2) |
C16 | 0.037 (2) | 0.061 (3) | 0.058 (2) | −0.010 (2) | 0.0090 (18) | −0.006 (2) |
C17 | 0.041 (2) | 0.063 (3) | 0.037 (2) | −0.008 (2) | 0.0094 (17) | 0.004 (2) |
C18 | 0.036 (2) | 0.042 (2) | 0.0320 (18) | 0.0036 (18) | −0.0003 (16) | −0.0003 (17) |
O18 | 0.0441 (15) | 0.0679 (18) | 0.0274 (13) | −0.0089 (14) | 0.0007 (11) | 0.0027 (12) |
C19 | 0.0316 (19) | 0.033 (2) | 0.0284 (18) | 0.0035 (17) | 0.0038 (15) | 0.0008 (15) |
C20 | 0.034 (2) | 0.041 (2) | 0.0360 (19) | 0.0033 (17) | −0.0008 (16) | −0.0032 (17) |
C1' | 0.037 (2) | 0.048 (2) | 0.0221 (16) | 0.0025 (18) | −0.0052 (15) | 0.0011 (16) |
O1' | 0.0416 (15) | 0.075 (2) | 0.0331 (14) | 0.0147 (14) | 0.0037 (11) | 0.0114 (14) |
C2' | 0.038 (2) | 0.047 (2) | 0.0252 (17) | 0.0027 (19) | 0.0039 (15) | 0.0019 (16) |
O2' | 0.0445 (15) | 0.0720 (19) | 0.0331 (13) | 0.0185 (15) | 0.0064 (11) | 0.0079 (13) |
C3' | 0.0348 (19) | 0.048 (2) | 0.0305 (18) | −0.0010 (19) | 0.0002 (15) | −0.0029 (17) |
O3' | 0.0462 (16) | 0.081 (2) | 0.0297 (13) | 0.0129 (15) | 0.0019 (11) | 0.0147 (14) |
C4' | 0.0344 (19) | 0.044 (2) | 0.0267 (17) | 0.0020 (18) | 0.0000 (15) | −0.0027 (16) |
O4' | 0.0405 (14) | 0.0704 (19) | 0.0318 (13) | 0.0163 (14) | 0.0085 (11) | 0.0024 (13) |
N1—C2 | 1.314 (4) | C13—C14 | 1.356 (5) |
N1—C9 | 1.366 (4) | C13—H13 | 0.9300 |
N1—H1 | 0.8600 | C14—C20 | 1.410 (5) |
C2—C3 | 1.390 (5) | C14—H14 | 0.9300 |
C2—H2 | 0.9300 | C15—C16 | 1.366 (5) |
C3—C4 | 1.361 (5) | C15—C20 | 1.409 (5) |
C3—H3 | 0.9300 | C15—H15 | 0.9300 |
C4—C10 | 1.418 (5) | C16—C17 | 1.403 (5) |
C4—H4 | 0.9300 | C16—H16 | 0.9300 |
C5—C6 | 1.352 (5) | C17—C18 | 1.370 (5) |
C5—C10 | 1.406 (5) | C17—H17 | 0.9300 |
C5—H5 | 0.9300 | C18—O18 | 1.355 (4) |
C6—C7 | 1.410 (5) | C18—C19 | 1.420 (4) |
C6—H6 | 0.9300 | O18—H18 | 0.8200 |
C7—C8 | 1.375 (5) | C19—C20 | 1.412 (4) |
C7—H7 | 0.9300 | C1'—O1' | 1.264 (4) |
C8—O8 | 1.347 (4) | C1'—C2' | 1.465 (5) |
C8—C9 | 1.423 (4) | C1'—C4' | 1.470 (4) |
O8—H8 | 0.8200 | C2'—O2' | 1.260 (4) |
C9—C10 | 1.409 (4) | C2'—C3' | 1.465 (4) |
N11—C12 | 1.321 (4) | C3'—O3' | 1.254 (4) |
N11—C19 | 1.373 (4) | C3'—O3' | 1.254 (4) |
N11—H11 | 0.8600 | C3'—C4' | 1.468 (4) |
C12—C13 | 1.381 (5) | C4'—O4' | 1.248 (4) |
C12—H12 | 0.9300 | ||
C2—N1—C9 | 122.0 (3) | C12—C13—H13 | 120.3 |
C2—N1—H1 | 119.0 | C13—C14—C20 | 120.6 (3) |
C9—N1—H1 | 119.0 | C13—C14—H14 | 119.7 |
N1—C2—C3 | 121.1 (3) | C20—C14—H14 | 119.7 |
N1—C2—H2 | 119.4 | C16—C15—C20 | 119.8 (3) |
C3—C2—H2 | 119.4 | C16—C15—H15 | 120.1 |
C4—C3—C2 | 119.7 (3) | C20—C15—H15 | 120.1 |
C4—C3—H3 | 120.2 | C15—C16—C17 | 121.0 (3) |
C2—C3—H3 | 120.2 | C15—C16—H16 | 119.5 |
C3—C4—C10 | 119.9 (3) | C17—C16—H16 | 119.5 |
C3—C4—H4 | 120.1 | C18—C17—C16 | 121.5 (3) |
C10—C4—H4 | 120.1 | C18—C17—H17 | 119.2 |
C6—C5—C10 | 120.4 (3) | C16—C17—H17 | 119.2 |
C6—C5—H5 | 119.8 | O18—C18—C17 | 125.2 (3) |
C10—C5—H5 | 119.8 | O18—C18—C19 | 116.9 (3) |
C5—C6—C7 | 120.8 (3) | C17—C18—C19 | 117.9 (3) |
C5—C6—H6 | 119.6 | C18—O18—H18 | 109.5 |
C7—C6—H6 | 119.6 | N11—C19—C20 | 118.5 (3) |
C8—C7—C6 | 121.5 (3) | N11—C19—C18 | 120.5 (3) |
C8—C7—H7 | 119.3 | C20—C19—C18 | 121.0 (3) |
C6—C7—H7 | 119.3 | C15—C20—C14 | 123.2 (3) |
O8—C8—C7 | 125.0 (3) | C15—C20—C19 | 118.8 (3) |
O8—C8—C9 | 117.4 (3) | C14—C20—C19 | 118.1 (3) |
C7—C8—C9 | 117.6 (3) | O1'—C1'—C2' | 135.3 (3) |
C8—O8—H8 | 109.5 | O1'—C1'—C4' | 134.4 (3) |
N1—C9—C10 | 119.4 (3) | C2'—C1'—C4' | 90.3 (2) |
N1—C9—C8 | 119.7 (3) | O2'—C2'—C3' | 137.0 (3) |
C10—C9—C8 | 120.9 (3) | O2'—C2'—C1' | 133.2 (3) |
C5—C10—C9 | 118.9 (3) | C3'—C2'—C1' | 89.8 (3) |
C5—C10—C4 | 123.2 (3) | O3'—C3'—O3' | 0.0 (2) |
C9—C10—C4 | 117.9 (3) | O3'—C3'—C2' | 133.9 (3) |
C12—N11—C19 | 122.1 (3) | O3'—C3'—C2' | 133.9 (3) |
C12—N11—H11 | 118.9 | O3'—C3'—C4' | 135.7 (3) |
C19—N11—H11 | 118.9 | O3'—C3'—C4' | 135.7 (3) |
N11—C12—C13 | 121.2 (3) | C2'—C3'—C4' | 90.4 (3) |
N11—C12—H12 | 119.4 | O3'—O3'—C3' | 0 (10) |
C13—C12—H12 | 119.4 | O4'—C4'—C3' | 134.4 (3) |
C14—C13—C12 | 119.4 (3) | O4'—C4'—C1' | 136.1 (3) |
C14—C13—H13 | 120.3 | C3'—C4'—C1' | 89.5 (3) |
D—H···A | D—H | H···A | D···A | D—H···A |
C7—H7···O1′i | 0.93 | 2.56 | 3.168 (4) | 123 |
O8—H8···O1′i | 0.82 | 1.78 | 2.596 (3) | 172 |
N1—H1···O2′ | 0.86 | 1.84 | 2.666 (4) | 159 |
C17—H17···O3′ | 0.93 | 2.48 | 3.138 (4) | 128 |
O18—H18···O3′ | 0.82 | 1.79 | 2.605 (3) | 169 |
N11—H11···O4′ii | 0.86 | 1.87 | 2.681 (4) | 157 |
Symmetry codes: (i) −x+1, −y+2, −z; (ii) −x, y−1/2, −z+1/2. |
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