Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536804018434/su6127sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536804018434/su6127Isup2.hkl |
CCDC reference: 248858
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.011 Å
- R factor = 0.075
- wR factor = 0.163
- Data-to-parameter ratio = 13.0
checkCIF/PLATON results
No syntax errors found
Alert level B PLAT340_ALERT_3_B Low Bond Precision on C-C bonds (x 1000) Ang ... 11 PLAT430_ALERT_2_B Short Inter D...A Contact O7 .. O8 .. 2.76 Ang.
Alert level C CELLV02_ALERT_1_C The supplied cell volume s.u. differs from that calculated from the cell parameter s.u.'s by > 2 Calculated cell volume su = 6.90 Cell volume su given = 4.00 PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ? PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ? PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given ....... ? PLAT152_ALERT_1_C Supplied and Calc Volume s.u. Inconsistent ..... ? PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 3.39 Ratio PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 3.31 Ratio PLAT222_ALERT_3_C Large Non-Solvent H Ueq(max)/Ueq(min) ... 3.35 Ratio PLAT222_ALERT_3_C Large Non-Solvent H Ueq(max)/Ueq(min) ... 3.23 Ratio PLAT230_ALERT_2_C Hirshfeld Test Diff for O1 - C9 .. 5.71 su PLAT242_ALERT_2_C Check Low U(eq) as Compared to Neighbors for C10
Alert level G REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is correct. If it is not, please give the correct count in the _publ_section_exptl_refinement section of the submitted CIF. From the CIF: _diffrn_reflns_theta_max 26.00 From the CIF: _reflns_number_total 3478 Count of symmetry unique reflns 2218 Completeness (_total/calc) 156.81% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 1260 Fraction of Friedel pairs measured 0.568 Are heavy atom types Z>Si present yes
0 ALERT level A = In general: serious problem 2 ALERT level B = Potentially serious problem 11 ALERT level C = Check and explain 1 ALERT level G = General alerts; check 4 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 5 ALERT type 2 Indicator that the structure model may be wrong or deficient 3 ALERT type 3 Indicator that the structure quality may be low 2 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: SMART (Siemens, 1996); cell refinement: SMART; data reduction: SAINT (Siemens, 1996); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997a); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997a); molecular graphics: SHELXTL (Sheldrick, 1997b); software used to prepare material for publication: SHELXTL.
C9H12NO2+·HSO4−·C9H11NO2 | F(000) = 452 |
Mr = 428.45 | Dx = 1.412 Mg m−3 |
Monoclinic, P21 | Mo Kα radiation, λ = 0.71073 Å |
a = 13.439 (3) Å | Cell parameters from 512 reflections |
b = 4.878 (3) Å | θ = 2.7–16.4° |
c = 15.483 (3) Å | µ = 0.21 mm−1 |
β = 97.05 (3)° | T = 293 K |
V = 1007.4 (4) Å3 | Block, colorless |
Z = 2 | 0.27 × 0.20 × 0.18 mm |
Bruker SMART CCD area-detector diffractometer | 3478 independent reflections |
Radiation source: fine-focus sealed tube | 2086 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.074 |
ω scans | θmax = 26.0°, θmin = 1.3° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −15→16 |
Tmin = 0.946, Tmax = 0.963 | k = −5→5 |
5540 measured reflections | l = −17→19 |
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)] = 0.075 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.163 | w = 1/[σ2(Fo2) + (0.0559P)2] where P = (Fo2 + 2Fc2)/3 |
S = 0.95 | (Δ/σ)max < 0.001 |
3478 reflections | Δρmax = 0.31 e Å−3 |
268 parameters | Δρmin = −0.39 e Å−3 |
2 restraints | Absolute structure: Flack (1983), 1260 Friedel pairs [CHECK] |
Primary atom site location: structure-invariant direct methods | Absolute structure parameter: 0.15 (19) |
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 | ||
S1 | 0.27011 (10) | 0.5458 (4) | 0.45100 (10) | 0.0339 (4) | |
O1 | 1.0188 (3) | −0.1526 (9) | 0.3637 (3) | 0.0312 (11) | |
H1 | 1.0762 | −0.1875 | 0.3852 | 0.047* | |
O2 | 1.0394 (3) | 0.2232 (10) | 0.4475 (3) | 0.0461 (13) | |
O3 | 0.3978 (2) | 1.0705 (10) | 0.5850 (3) | 0.0373 (11) | |
O4 | 0.3241 (3) | 0.9620 (11) | 0.7018 (3) | 0.0450 (14) | |
O5 | 0.3753 (2) | 0.6202 (9) | 0.4369 (2) | 0.0320 (11) | |
O6 | 0.2655 (3) | 0.4295 (10) | 0.5452 (2) | 0.0331 (11) | |
O7 | 0.1957 (2) | 0.7826 (10) | 0.4402 (2) | 0.0329 (11) | |
O8 | 0.2327 (3) | 0.3076 (10) | 0.3856 (2) | 0.0371 (12) | |
C7 | 0.9085 (4) | 0.2769 (15) | 0.2492 (4) | 0.0345 (16) | |
H7A | 0.8620 | 0.4251 | 0.2324 | 0.041* | |
H7B | 0.9759 | 0.3474 | 0.2483 | 0.041* | |
N1 | 0.8619 (3) | 0.4276 (11) | 0.3908 (3) | 0.0327 (13) | |
H1A | 0.8502 | 0.3747 | 0.4436 | 0.049* | |
H1B | 0.8059 | 0.4954 | 0.3621 | 0.049* | |
H1C | 0.9093 | 0.5561 | 0.3956 | 0.049* | |
C16 | 0.5368 (4) | 0.7803 (15) | 0.7527 (4) | 0.0388 (17) | |
H16A | 0.5847 | 0.9083 | 0.7335 | 0.047* | |
H16B | 0.4995 | 0.8773 | 0.7930 | 0.047* | |
N2 | 0.5165 (3) | 0.6421 (11) | 0.5962 (3) | 0.0299 (13) | |
H2A | 0.4727 | 0.6453 | 0.5482 | 0.045* | |
H2B | 0.5456 | 0.4782 | 0.6017 | 0.045* | |
H2C | 0.5630 | 0.7702 | 0.5926 | 0.045* | |
C1 | 0.8908 (4) | 0.0509 (16) | 0.1836 (3) | 0.0360 (15) | |
C2 | 0.7954 (5) | −0.0559 (17) | 0.1596 (4) | 0.053 (2) | |
H2 | 0.7419 | 0.0100 | 0.1864 | 0.063* | |
C3 | 0.7786 (7) | −0.255 (2) | 0.0978 (5) | 0.068 (3) | |
H3 | 0.7141 | −0.3232 | 0.0833 | 0.081* | |
C4 | 0.8538 (8) | −0.353 (2) | 0.0579 (5) | 0.081 (3) | |
H4 | 0.8413 | −0.4889 | 0.0157 | 0.097* | |
C5 | 0.9503 (8) | −0.2547 (19) | 0.0790 (5) | 0.076 (3) | |
H5 | 1.0028 | −0.3246 | 0.0517 | 0.092* | |
C6 | 0.9679 (5) | −0.0484 (17) | 0.1417 (4) | 0.052 (2) | |
H6A | 1.0322 | 0.0222 | 0.1553 | 0.062* | |
C8 | 0.8961 (4) | 0.1874 (13) | 0.3424 (3) | 0.0240 (14) | |
H8A | 0.8457 | 0.0417 | 0.3404 | 0.029* | |
C9 | 0.9921 (4) | 0.0884 (16) | 0.3916 (4) | 0.0315 (17) | |
C10 | 0.5940 (4) | 0.5522 (17) | 0.8014 (4) | 0.0368 (15) | |
C11 | 0.5590 (7) | 0.441 (2) | 0.8735 (5) | 0.073 (3) | |
H11 | 0.4986 | 0.5006 | 0.8904 | 0.088* | |
C12 | 0.6164 (8) | 0.231 (2) | 0.9227 (5) | 0.081 (3) | |
H12 | 0.5942 | 0.1529 | 0.9716 | 0.097* | |
C13 | 0.7030 (8) | 0.154 (2) | 0.8954 (6) | 0.092 (4) | |
H13 | 0.7409 | 0.0205 | 0.9274 | 0.110* | |
C14 | 0.7387 (6) | 0.258 (2) | 0.8240 (6) | 0.074 (3) | |
H14 | 0.7976 | 0.1927 | 0.8054 | 0.089* | |
C15 | 0.6835 (5) | 0.4642 (17) | 0.7801 (5) | 0.056 (2) | |
H15 | 0.7090 | 0.5475 | 0.7335 | 0.067* | |
C17 | 0.4634 (4) | 0.6968 (14) | 0.6734 (3) | 0.0282 (15) | |
H17 | 0.4275 | 0.5309 | 0.6874 | 0.034* | |
C18 | 0.3876 (4) | 0.9292 (15) | 0.6518 (4) | 0.0312 (16) | |
H6 | 0.308 (4) | 0.306 (12) | 0.556 (4) | 0.080* |
U11 | U22 | U33 | U12 | U13 | U23 | |
S1 | 0.0259 (7) | 0.0337 (11) | 0.0422 (9) | 0.0037 (9) | 0.0047 (6) | −0.0011 (9) |
O1 | 0.023 (2) | 0.025 (3) | 0.043 (3) | 0.007 (2) | −0.0055 (18) | −0.007 (2) |
O2 | 0.034 (2) | 0.029 (3) | 0.070 (3) | −0.004 (2) | −0.013 (2) | −0.005 (3) |
O3 | 0.032 (2) | 0.027 (3) | 0.053 (3) | 0.010 (2) | 0.0064 (19) | 0.004 (3) |
O4 | 0.027 (2) | 0.066 (4) | 0.042 (3) | 0.007 (2) | 0.0041 (18) | −0.007 (3) |
O5 | 0.0196 (19) | 0.030 (3) | 0.048 (2) | 0.003 (2) | 0.0103 (17) | 0.000 (2) |
O6 | 0.032 (2) | 0.040 (3) | 0.029 (2) | 0.014 (2) | 0.0068 (18) | 0.007 (2) |
O7 | 0.020 (2) | 0.029 (3) | 0.050 (3) | 0.014 (2) | 0.0036 (18) | 0.000 (2) |
O8 | 0.042 (2) | 0.033 (3) | 0.036 (2) | −0.010 (2) | 0.0034 (19) | −0.008 (2) |
C7 | 0.041 (3) | 0.027 (4) | 0.038 (4) | 0.005 (3) | 0.012 (3) | 0.009 (3) |
N1 | 0.026 (3) | 0.031 (4) | 0.041 (3) | 0.000 (3) | 0.001 (2) | 0.000 (3) |
C16 | 0.043 (4) | 0.026 (5) | 0.044 (4) | 0.008 (4) | −0.007 (3) | −0.010 (3) |
N2 | 0.021 (2) | 0.025 (4) | 0.043 (3) | 0.003 (2) | 0.001 (2) | 0.000 (2) |
C1 | 0.055 (4) | 0.028 (4) | 0.024 (3) | 0.005 (4) | 0.005 (3) | 0.007 (3) |
C2 | 0.062 (5) | 0.043 (6) | 0.049 (4) | 0.010 (4) | −0.008 (3) | −0.003 (4) |
C3 | 0.088 (6) | 0.050 (7) | 0.056 (5) | −0.007 (6) | −0.026 (5) | 0.012 (5) |
C4 | 0.144 (9) | 0.055 (7) | 0.038 (5) | −0.004 (7) | −0.011 (6) | 0.002 (4) |
C5 | 0.147 (9) | 0.040 (6) | 0.053 (5) | 0.016 (6) | 0.056 (6) | 0.004 (5) |
C6 | 0.075 (5) | 0.042 (6) | 0.042 (4) | 0.007 (4) | 0.021 (4) | 0.006 (4) |
C8 | 0.022 (3) | 0.016 (4) | 0.033 (3) | −0.002 (3) | 0.001 (2) | −0.004 (3) |
C9 | 0.021 (3) | 0.036 (5) | 0.038 (4) | −0.007 (3) | 0.006 (3) | 0.015 (4) |
C10 | 0.044 (3) | 0.028 (4) | 0.037 (3) | 0.000 (4) | −0.004 (3) | −0.001 (4) |
C11 | 0.107 (6) | 0.064 (7) | 0.048 (5) | −0.007 (6) | 0.006 (4) | 0.000 (5) |
C12 | 0.145 (9) | 0.055 (8) | 0.039 (5) | −0.018 (7) | −0.002 (6) | 0.009 (5) |
C13 | 0.136 (9) | 0.057 (8) | 0.065 (7) | 0.006 (7) | −0.058 (6) | 0.004 (6) |
C14 | 0.061 (5) | 0.052 (7) | 0.100 (7) | 0.006 (5) | −0.025 (5) | −0.002 (6) |
C15 | 0.051 (4) | 0.043 (6) | 0.070 (5) | −0.001 (4) | −0.011 (4) | 0.009 (4) |
C17 | 0.027 (3) | 0.023 (4) | 0.033 (3) | 0.000 (3) | 0.002 (3) | 0.005 (3) |
C18 | 0.025 (3) | 0.026 (4) | 0.041 (4) | −0.002 (3) | −0.006 (3) | −0.008 (3) |
S1—O5 | 1.501 (3) | C1—C6 | 1.377 (8) |
S1—O7 | 1.523 (4) | C1—C2 | 1.391 (9) |
S1—O6 | 1.574 (4) | C2—C3 | 1.363 (11) |
S1—O8 | 1.582 (4) | C2—H2 | 0.9300 |
O1—C9 | 1.317 (8) | C3—C4 | 1.337 (10) |
O1—H1 | 0.8200 | C3—H3 | 0.9300 |
O2—C9 | 1.205 (7) | C4—C5 | 1.384 (12) |
O3—C18 | 1.264 (7) | C4—H4 | 0.9300 |
O4—C18 | 1.231 (6) | C5—C6 | 1.399 (11) |
O6—H6 | 0.83 (6) | C5—H5 | 0.9300 |
C7—C1 | 1.498 (9) | C6—H6A | 0.9300 |
C7—C8 | 1.536 (7) | C8—C9 | 1.495 (7) |
C7—H7A | 0.9700 | C8—H8A | 0.9800 |
C7—H7B | 0.9700 | C10—C15 | 1.355 (8) |
N1—C8 | 1.493 (7) | C10—C11 | 1.375 (9) |
N1—H1A | 0.8900 | C11—C12 | 1.441 (12) |
N1—H1B | 0.8900 | C11—H11 | 0.9300 |
N1—H1C | 0.8900 | C12—C13 | 1.341 (12) |
C16—C10 | 1.501 (9) | C12—H12 | 0.9300 |
C16—C17 | 1.533 (7) | C13—C14 | 1.357 (11) |
C16—H16A | 0.9700 | C13—H13 | 0.9300 |
C16—H16B | 0.9700 | C14—C15 | 1.380 (11) |
N2—C17 | 1.489 (6) | C14—H14 | 0.9300 |
N2—H2A | 0.8900 | C15—H15 | 0.9300 |
N2—H2B | 0.8900 | C17—C18 | 1.533 (9) |
N2—H2C | 0.8900 | C17—H17 | 0.9800 |
O5—S1—O7 | 114.7 (2) | C5—C4—H4 | 119.8 |
O5—S1—O6 | 111.5 (2) | C4—C5—C6 | 119.2 (8) |
O7—S1—O6 | 105.9 (2) | C4—C5—H5 | 120.4 |
O5—S1—O8 | 108.4 (2) | C6—C5—H5 | 120.4 |
O7—S1—O8 | 109.5 (2) | C1—C6—C5 | 120.5 (8) |
O6—S1—O8 | 106.4 (3) | C1—C6—H6A | 119.8 |
C9—O1—H1 | 109.5 | C5—C6—H6A | 119.8 |
S1—O6—H6 | 110 (5) | N1—C8—C9 | 107.3 (5) |
C1—C7—C8 | 113.6 (6) | N1—C8—C7 | 108.9 (5) |
C1—C7—H7A | 108.8 | C9—C8—C7 | 112.6 (4) |
C8—C7—H7A | 108.8 | N1—C8—H8A | 109.4 |
C1—C7—H7B | 108.8 | C9—C8—H8A | 109.4 |
C8—C7—H7B | 108.8 | C7—C8—H8A | 109.4 |
H7A—C7—H7B | 107.7 | O2—C9—O1 | 125.5 (6) |
C8—N1—H1A | 109.5 | O2—C9—C8 | 122.4 (7) |
C8—N1—H1B | 109.5 | O1—C9—C8 | 112.0 (6) |
H1A—N1—H1B | 109.5 | C15—C10—C11 | 118.3 (7) |
C8—N1—H1C | 109.5 | C15—C10—C16 | 121.9 (6) |
H1A—N1—H1C | 109.5 | C11—C10—C16 | 119.7 (7) |
H1B—N1—H1C | 109.5 | C10—C11—C12 | 119.7 (8) |
C10—C16—C17 | 116.4 (6) | C10—C11—H11 | 120.1 |
C10—C16—H16A | 108.2 | C12—C11—H11 | 120.1 |
C17—C16—H16A | 108.2 | C13—C12—C11 | 117.6 (8) |
C10—C16—H16B | 108.2 | C13—C12—H12 | 121.2 |
C17—C16—H16B | 108.2 | C11—C12—H12 | 121.2 |
H16A—C16—H16B | 107.3 | C12—C13—C14 | 124.0 (9) |
C17—N2—H2A | 109.5 | C12—C13—H13 | 118.0 |
C17—N2—H2B | 109.5 | C14—C13—H13 | 118.0 |
H2A—N2—H2B | 109.5 | C13—C14—C15 | 116.8 (9) |
C17—N2—H2C | 109.5 | C13—C14—H14 | 121.6 |
H2A—N2—H2C | 109.5 | C15—C14—H14 | 121.6 |
H2B—N2—H2C | 109.5 | C10—C15—C14 | 123.5 (8) |
C6—C1—C2 | 117.7 (7) | C10—C15—H15 | 118.2 |
C6—C1—C7 | 120.8 (6) | C14—C15—H15 | 118.2 |
C2—C1—C7 | 121.5 (6) | N2—C17—C16 | 111.5 (4) |
C3—C2—C1 | 121.5 (7) | N2—C17—C18 | 109.2 (5) |
C3—C2—H2 | 119.2 | C16—C17—C18 | 108.9 (5) |
C1—C2—H2 | 119.2 | N2—C17—H17 | 109.1 |
C4—C3—C2 | 120.7 (8) | C16—C17—H17 | 109.1 |
C4—C3—H3 | 119.6 | C18—C17—H17 | 109.1 |
C2—C3—H3 | 119.6 | O4—C18—O3 | 126.7 (6) |
C3—C4—C5 | 120.4 (9) | O4—C18—C17 | 116.9 (6) |
C3—C4—H4 | 119.8 | O3—C18—C17 | 116.4 (5) |
D—H···A | D—H | H···A | D···A | D—H···A |
O6—H6···O3i | 0.83 (6) | 1.69 (6) | 2.519 (5) | 176 (8) |
N2—H2C···O5ii | 0.89 | 1.98 | 2.828 (6) | 160 |
N2—H2B···O5iii | 0.89 | 2.17 | 3.007 (6) | 157 |
N2—H2A···O5 | 0.89 | 2.04 | 2.923 (6) | 175 |
N1—H1C···O2iv | 0.89 | 2.57 | 3.047 (6) | 114 |
N1—H1C···O1v | 0.89 | 2.15 | 3.005 (6) | 162 |
N1—H1B···O4iii | 0.89 | 1.91 | 2.730 (6) | 153 |
N1—H1A···O7iii | 0.89 | 2.02 | 2.905 (6) | 172 |
O1—H1···O7vi | 0.82 | 1.73 | 2.543 (5) | 171 |
Symmetry codes: (i) x, y−1, z; (ii) −x+1, y+1/2, −z+1; (iii) −x+1, y−1/2, −z+1; (iv) −x+2, y+1/2, −z+1; (v) x, y+1, z; (vi) x+1, y−1, z. |
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