Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536804028867/hb6113sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536804028867/hb6113Isup2.hkl |
CCDC reference: 259588
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.002 Å
- R factor = 0.054
- wR factor = 0.155
- Data-to-parameter ratio = 12.7
checkCIF/PLATON results
No syntax errors found
Alert level A PLAT029_ALERT_3_A _diffrn_measured_fraction_theta_full Low ....... 0.92
Alert level C REFLT03_ALERT_3_C Reflection count < 95% complete From the CIF: _diffrn_reflns_theta_max 68.90 From the CIF: _diffrn_reflns_theta_full 0.00 From the CIF: _reflns_number_total 3268 TEST2: Reflns within _diffrn_reflns_theta_max Count of symmetry unique reflns 3567 Completeness (_total/calc) 91.62% PLAT022_ALERT_3_C Ratio Unique / Expected Reflections too Low .... 0.92 PLAT063_ALERT_3_C Crystal Probably too Large for Beam Size ....... 0.68 mm PLAT244_ALERT_4_C Low Solvent U(eq) as Compared to Neighbors for C19 PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor .... 2.25
1 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 5 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 4 ALERT type 3 Indicator that the structure quality may be low 1 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: XSCANS (Bruker, 2001); cell refinement: XSCANS; data reduction: SHELXTL (Bruker, 2001); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 1990); software used to prepare material for publication: PLATON.
C14H19N4O3+·C3H3O4− | Z = 2 |
Mr = 394.39 | F(000) = 416 |
Triclinic, P1 | Dx = 1.366 Mg m−3 |
Hall symbol: -P 1 | Cu Kα radiation, λ = 1.54178 Å |
a = 8.4851 (2) Å | Cell parameters from 50 reflections |
b = 8.6566 (2) Å | θ = 2.1–28.1° |
c = 13.6425 (3) Å | µ = 0.91 mm−1 |
α = 106.360 (3)° | T = 293 K |
β = 91.712 (2)° | Plate, colorless |
γ = 92.950 (3)° | 0.68 × 0.65 × 0.35 mm |
V = 959.08 (4) Å3 |
Bruker P4 diffractometer | 3029 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.020 |
Graphite monochromator | θmax = 68.9°, θmin = 3.4° |
ω scans | h = 0→10 |
Absorption correction: part of the refinement model (ΔF) SHELXA (Bruker, 2001) | k = −10→9 |
Tmin = 0.549, Tmax = 0.726 | l = −16→16 |
3484 measured reflections | 3 standard reflections every 97 reflections |
3268 independent reflections | intensity decay: none |
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.054 | H-atom parameters constrained |
wR(F2) = 0.156 | w = 1/[σ2(Fo2) + (0.0825P)2 + 0.208P] where P = (Fo2 + 2Fc2)/3 |
S = 1.07 | (Δ/σ)max < 0.001 |
3268 reflections | Δρmax = 0.15 e Å−3 |
258 parameters | Δρmin = −0.20 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: 0.016 (2) |
Experimental. The low data completeness (92%) arose due to problems in accessing all parts of reciprocal space at high angles (2θ = 138°) for a triclinic crystal collected using copper radiation. |
Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All e.s.d.'s are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles |
Refinement. Refinement on F2 for ALL reflections except those flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The observed criterion of F2 > σ(F2) is used only for calculating -R-factor-obs 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 | ||
O1 | 0.60422 (16) | 0.19447 (18) | 0.66944 (10) | 0.0635 (5) | |
O2 | 0.29781 (16) | 0.11037 (17) | 0.64647 (10) | 0.0620 (4) | |
O3 | 0.12262 (16) | 0.1503 (2) | 0.48835 (10) | 0.0722 (5) | |
N1 | 0.3900 (2) | 0.41033 (18) | 0.11787 (11) | 0.0578 (5) | |
N2 | 0.2603 (2) | 0.2447 (2) | −0.02719 (13) | 0.0746 (7) | |
N3 | 0.3824 (2) | 0.12923 (18) | 0.08431 (12) | 0.0595 (5) | |
N4 | 0.4950 (2) | 0.0105 (2) | 0.19461 (13) | 0.0676 (6) | |
C2 | 0.3453 (2) | 0.2601 (2) | 0.05907 (14) | 0.0564 (6) | |
C4 | 0.4633 (2) | 0.1467 (2) | 0.17320 (14) | 0.0546 (6) | |
C5 | 0.5132 (2) | 0.3023 (2) | 0.24014 (13) | 0.0539 (6) | |
C6 | 0.4728 (2) | 0.4284 (2) | 0.20754 (14) | 0.0558 (6) | |
C7 | 0.6048 (2) | 0.3261 (3) | 0.34030 (14) | 0.0603 (6) | |
C8 | 0.5172 (2) | 0.2756 (2) | 0.42258 (13) | 0.0513 (5) | |
C9 | 0.6041 (2) | 0.2604 (2) | 0.50718 (13) | 0.0524 (6) | |
C10 | 0.5297 (2) | 0.2106 (2) | 0.58268 (13) | 0.0508 (5) | |
C11 | 0.3677 (2) | 0.1733 (2) | 0.57452 (13) | 0.0512 (6) | |
C12 | 0.2803 (2) | 0.1915 (2) | 0.49096 (13) | 0.0544 (6) | |
C13 | 0.3555 (2) | 0.2447 (2) | 0.41588 (14) | 0.0567 (6) | |
C14 | 0.0276 (2) | 0.1698 (3) | 0.40559 (18) | 0.0797 (9) | |
C15 | 0.2035 (3) | 0.2178 (3) | 0.71531 (16) | 0.0734 (8) | |
C16 | 0.7715 (3) | 0.2277 (4) | 0.68101 (17) | 0.0807 (9) | |
O4 | 0.3144 (2) | 0.67550 (18) | 0.06300 (12) | 0.0779 (6) | |
O5 | 0.1735 (2) | 0.52666 (18) | −0.07463 (13) | 0.0841 (6) | |
O6 | 0.0763 (3) | 0.9271 (2) | −0.15728 (14) | 0.0982 (8) | |
O7 | 0.0414 (3) | 0.6641 (2) | −0.19174 (13) | 0.0942 (7) | |
C17 | 0.2203 (3) | 0.6593 (2) | −0.01213 (15) | 0.0624 (7) | |
C18 | 0.1600 (3) | 0.8112 (2) | −0.02884 (16) | 0.0700 (8) | |
C19 | 0.0895 (3) | 0.8053 (3) | −0.13153 (16) | 0.0686 (7) | |
H1 | 0.36630 | 0.49330 | 0.09890 | 0.0690* | |
H2A | 0.23010 | 0.15030 | −0.06590 | 0.0900* | |
H2B | 0.23570 | 0.32910 | −0.04420 | 0.0900* | |
H4A | 0.46400 | −0.08100 | 0.15260 | 0.0810* | |
H4B | 0.54650 | 0.01400 | 0.25050 | 0.0810* | |
H6 | 0.50280 | 0.53210 | 0.24800 | 0.0670* | |
H7A | 0.63880 | 0.43940 | 0.36680 | 0.0720* | |
H7B | 0.69900 | 0.26600 | 0.32690 | 0.0720* | |
H9 | 0.71270 | 0.28390 | 0.51290 | 0.0630* | |
H13 | 0.29640 | 0.25950 | 0.36110 | 0.0680* | |
H14A | −0.07850 | 0.12810 | 0.40930 | 0.1200* | |
H14B | 0.06980 | 0.11220 | 0.34210 | 0.1200* | |
H14C | 0.02720 | 0.28230 | 0.40950 | 0.1200* | |
H15A | 0.14000 | 0.15870 | 0.75130 | 0.1100* | |
H15B | 0.13600 | 0.26890 | 0.67770 | 0.1100* | |
H15C | 0.27060 | 0.29850 | 0.76350 | 0.1100* | |
H16A | 0.81000 | 0.20750 | 0.74280 | 0.1210* | |
H16B | 0.79610 | 0.33860 | 0.68430 | 0.1210* | |
H16C | 0.82070 | 0.15930 | 0.62360 | 0.1210* | |
H7 | 0.05530 | 0.59500 | −0.16240 | 0.1410* | |
H18A | 0.08110 | 0.84870 | 0.02100 | 0.0840* | |
H18B | 0.24720 | 0.89260 | −0.01330 | 0.0840* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0627 (8) | 0.0821 (9) | 0.0515 (7) | 0.0097 (7) | −0.0057 (6) | 0.0283 (7) |
O2 | 0.0719 (8) | 0.0663 (8) | 0.0520 (7) | 0.0025 (6) | 0.0085 (6) | 0.0236 (6) |
O3 | 0.0555 (7) | 0.1081 (12) | 0.0538 (8) | −0.0108 (7) | −0.0041 (6) | 0.0277 (8) |
N1 | 0.0766 (10) | 0.0482 (9) | 0.0496 (8) | 0.0046 (7) | −0.0040 (7) | 0.0163 (7) |
N2 | 0.1130 (15) | 0.0535 (10) | 0.0560 (9) | 0.0054 (9) | −0.0241 (9) | 0.0164 (8) |
N3 | 0.0798 (10) | 0.0494 (9) | 0.0499 (8) | 0.0066 (8) | −0.0045 (7) | 0.0156 (7) |
N4 | 0.0924 (12) | 0.0582 (10) | 0.0557 (9) | 0.0137 (9) | −0.0052 (8) | 0.0210 (8) |
C2 | 0.0721 (11) | 0.0511 (10) | 0.0470 (9) | 0.0047 (8) | −0.0016 (8) | 0.0160 (8) |
C4 | 0.0645 (10) | 0.0546 (10) | 0.0483 (9) | 0.0083 (8) | 0.0046 (8) | 0.0197 (8) |
C5 | 0.0587 (10) | 0.0598 (11) | 0.0450 (9) | 0.0006 (8) | 0.0036 (7) | 0.0183 (8) |
C6 | 0.0657 (11) | 0.0540 (10) | 0.0458 (9) | −0.0018 (8) | 0.0001 (8) | 0.0124 (8) |
C7 | 0.0586 (10) | 0.0742 (13) | 0.0511 (10) | −0.0040 (9) | −0.0026 (8) | 0.0246 (9) |
C8 | 0.0571 (9) | 0.0523 (10) | 0.0441 (9) | 0.0032 (8) | −0.0002 (7) | 0.0135 (7) |
C9 | 0.0522 (9) | 0.0576 (11) | 0.0475 (9) | 0.0032 (8) | −0.0014 (7) | 0.0155 (8) |
C10 | 0.0593 (10) | 0.0505 (9) | 0.0421 (8) | 0.0078 (8) | −0.0022 (7) | 0.0120 (7) |
C11 | 0.0597 (10) | 0.0512 (10) | 0.0426 (9) | 0.0010 (8) | 0.0010 (7) | 0.0137 (7) |
C12 | 0.0527 (9) | 0.0631 (11) | 0.0452 (9) | −0.0019 (8) | −0.0011 (7) | 0.0131 (8) |
C13 | 0.0571 (10) | 0.0674 (12) | 0.0462 (9) | 0.0001 (8) | −0.0045 (7) | 0.0186 (8) |
C14 | 0.0554 (11) | 0.1133 (19) | 0.0723 (14) | −0.0038 (11) | −0.0119 (10) | 0.0325 (13) |
C15 | 0.0799 (14) | 0.0850 (15) | 0.0553 (11) | 0.0033 (11) | 0.0167 (10) | 0.0189 (10) |
C16 | 0.0608 (12) | 0.122 (2) | 0.0631 (12) | 0.0161 (12) | −0.0080 (10) | 0.0319 (13) |
O4 | 0.1069 (12) | 0.0603 (9) | 0.0689 (9) | 0.0083 (8) | −0.0197 (8) | 0.0241 (7) |
O5 | 0.1248 (14) | 0.0512 (8) | 0.0736 (10) | 0.0058 (8) | −0.0188 (9) | 0.0154 (7) |
O6 | 0.1482 (17) | 0.0711 (11) | 0.0812 (11) | 0.0053 (10) | −0.0288 (11) | 0.0349 (9) |
O7 | 0.1392 (16) | 0.0670 (10) | 0.0708 (10) | 0.0016 (10) | −0.0343 (10) | 0.0151 (8) |
C17 | 0.0801 (13) | 0.0551 (11) | 0.0542 (10) | 0.0060 (9) | 0.0008 (9) | 0.0192 (9) |
C18 | 0.0935 (15) | 0.0553 (12) | 0.0602 (12) | 0.0097 (10) | −0.0121 (11) | 0.0153 (9) |
C19 | 0.0872 (14) | 0.0592 (12) | 0.0602 (12) | 0.0069 (10) | −0.0071 (10) | 0.0189 (9) |
O1—C10 | 1.370 (2) | C7—C8 | 1.515 (3) |
O1—C16 | 1.429 (3) | C8—C9 | 1.392 (2) |
O2—C11 | 1.384 (2) | C8—C13 | 1.380 (2) |
O2—C15 | 1.420 (3) | C9—C10 | 1.381 (2) |
O3—C12 | 1.364 (2) | C10—C11 | 1.390 (2) |
O3—C14 | 1.421 (3) | C11—C12 | 1.392 (2) |
O4—C17 | 1.252 (3) | C12—C13 | 1.394 (3) |
O5—C17 | 1.259 (3) | C6—H6 | 0.9296 |
O6—C19 | 1.211 (3) | C7—H7B | 0.9700 |
O7—C19 | 1.303 (3) | C7—H7A | 0.9699 |
O7—H7 | 0.8193 | C9—H9 | 0.9295 |
N1—C6 | 1.358 (2) | C13—H13 | 0.9298 |
N1—C2 | 1.350 (2) | C14—H14B | 0.9595 |
N2—C2 | 1.332 (2) | C14—H14C | 0.9603 |
N3—C2 | 1.323 (2) | C14—H14A | 0.9607 |
N3—C4 | 1.342 (2) | C15—H15A | 0.9602 |
N4—C4 | 1.330 (3) | C15—H15C | 0.9604 |
N1—H1 | 0.8600 | C15—H15B | 0.9609 |
N2—H2B | 0.8599 | C16—H16B | 0.9600 |
N2—H2A | 0.8599 | C16—H16A | 0.9593 |
N4—H4A | 0.8595 | C16—H16C | 0.9602 |
N4—H4B | 0.8596 | C17—C18 | 1.508 (3) |
C4—C5 | 1.433 (3) | C18—C19 | 1.493 (3) |
C5—C6 | 1.345 (3) | C18—H18A | 0.9701 |
C5—C7 | 1.508 (2) | C18—H18B | 0.9704 |
C10—O1—C16 | 117.44 (16) | C5—C6—H6 | 118.69 |
C11—O2—C15 | 114.76 (16) | C5—C7—H7B | 108.29 |
C12—O3—C14 | 117.60 (15) | C8—C7—H7A | 108.26 |
C19—O7—H7 | 109.49 | C5—C7—H7A | 108.30 |
C2—N1—C6 | 118.94 (16) | H7A—C7—H7B | 107.44 |
C2—N3—C4 | 118.74 (16) | C8—C7—H7B | 108.35 |
C6—N1—H1 | 120.52 | C10—C9—H9 | 119.83 |
C2—N1—H1 | 120.53 | C8—C9—H9 | 119.88 |
C2—N2—H2A | 119.96 | C8—C13—H13 | 119.89 |
C2—N2—H2B | 120.02 | C12—C13—H13 | 119.84 |
H2A—N2—H2B | 120.01 | O3—C14—H14B | 109.49 |
C4—N4—H4A | 120.04 | O3—C14—H14C | 109.50 |
H4A—N4—H4B | 119.98 | O3—C14—H14A | 109.43 |
C4—N4—H4B | 119.98 | H14A—C14—H14C | 109.48 |
N2—C2—N3 | 119.40 (17) | H14B—C14—H14C | 109.43 |
N1—C2—N2 | 118.16 (17) | H14A—C14—H14B | 109.48 |
N1—C2—N3 | 122.44 (17) | O2—C15—H15A | 109.48 |
N3—C4—C5 | 121.97 (16) | O2—C15—H15C | 109.52 |
N4—C4—C5 | 122.32 (17) | H15A—C15—H15B | 109.46 |
N3—C4—N4 | 115.72 (17) | O2—C15—H15B | 109.46 |
C6—C5—C7 | 121.47 (18) | H15B—C15—H15C | 109.48 |
C4—C5—C6 | 115.24 (16) | H15A—C15—H15C | 109.42 |
C4—C5—C7 | 123.29 (17) | O1—C16—H16B | 109.46 |
N1—C6—C5 | 122.65 (17) | O1—C16—H16C | 109.44 |
C5—C7—C8 | 115.91 (15) | O1—C16—H16A | 109.46 |
C7—C8—C9 | 118.33 (15) | H16A—C16—H16C | 109.50 |
C9—C8—C13 | 119.59 (16) | H16B—C16—H16C | 109.46 |
C7—C8—C13 | 122.08 (16) | H16A—C16—H16B | 109.50 |
C8—C9—C10 | 120.29 (16) | O4—C17—C18 | 117.03 (18) |
O1—C10—C11 | 114.89 (15) | O5—C17—C18 | 117.93 (19) |
C9—C10—C11 | 120.43 (16) | O4—C17—O5 | 125.03 (19) |
O1—C10—C9 | 124.69 (16) | C17—C18—C19 | 118.88 (18) |
O2—C11—C12 | 121.21 (15) | O6—C19—C18 | 121.2 (2) |
O2—C11—C10 | 119.40 (15) | O7—C19—C18 | 117.3 (2) |
C10—C11—C12 | 119.29 (16) | O6—C19—O7 | 121.5 (2) |
O3—C12—C11 | 115.42 (15) | C17—C18—H18A | 107.63 |
C11—C12—C13 | 120.06 (16) | C17—C18—H18B | 107.62 |
O3—C12—C13 | 124.50 (16) | C19—C18—H18A | 107.62 |
C8—C13—C12 | 120.27 (16) | C19—C18—H18B | 107.52 |
N1—C6—H6 | 118.66 | H18A—C18—H18B | 107.03 |
C16—O1—C10—C9 | −1.7 (3) | C5—C7—C8—C9 | 165.84 (17) |
C16—O1—C10—C11 | 178.6 (2) | C13—C8—C9—C10 | 1.7 (3) |
C15—O2—C11—C10 | 108.4 (2) | C7—C8—C13—C12 | 177.10 (18) |
C15—O2—C11—C12 | −75.3 (2) | C9—C8—C13—C12 | −2.9 (3) |
C14—O3—C12—C11 | 178.76 (18) | C7—C8—C9—C10 | −178.30 (18) |
C14—O3—C12—C13 | −2.9 (3) | C8—C9—C10—C11 | 0.8 (3) |
C6—N1—C2—N3 | −1.7 (3) | C8—C9—C10—O1 | −178.89 (17) |
C6—N1—C2—N2 | 178.11 (17) | C9—C10—C11—O2 | 174.43 (16) |
C2—N1—C6—C5 | 0.4 (3) | C9—C10—C11—C12 | −2.0 (3) |
C4—N3—C2—N2 | −177.67 (17) | O1—C10—C11—C12 | 177.68 (16) |
C4—N3—C2—N1 | 2.1 (3) | O1—C10—C11—O2 | −5.9 (2) |
C2—N3—C4—C5 | −1.3 (3) | O2—C11—C12—C13 | −175.57 (16) |
C2—N3—C4—N4 | 179.15 (17) | C10—C11—C12—C13 | 0.8 (3) |
N4—C4—C5—C6 | 179.66 (17) | O2—C11—C12—O3 | 2.9 (3) |
N3—C4—C5—C6 | 0.2 (3) | C10—C11—C12—O3 | 179.22 (16) |
N4—C4—C5—C7 | −0.3 (3) | C11—C12—C13—C8 | 1.7 (3) |
N3—C4—C5—C7 | −179.74 (16) | O3—C12—C13—C8 | −176.60 (17) |
C6—C5—C7—C8 | 113.4 (2) | O4—C17—C18—C19 | 161.5 (2) |
C4—C5—C7—C8 | −66.7 (2) | O5—C17—C18—C19 | −18.0 (3) |
C4—C5—C6—N1 | 0.3 (3) | C17—C18—C19—O7 | 19.6 (3) |
C7—C5—C6—N1 | −179.80 (16) | C17—C18—C19—O6 | −161.1 (2) |
C5—C7—C8—C13 | −14.2 (3) |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1···O4 | 0.86 | 1.85 | 2.708 (2) | 178 |
N2—H2A···O6i | 0.86 | 2.30 | 3.129 (3) | 163 |
N2—H2B···O5 | 0.86 | 1.96 | 2.822 (2) | 176 |
N4—H4A···O4i | 0.86 | 2.39 | 3.229 (2) | 164 |
N4—H4B···O2ii | 0.86 | 2.40 | 3.182 (2) | 151 |
O7—H7···O5 | 0.82 | 1.78 | 2.515 (3) | 148 |
C6—H6···O1iii | 0.93 | 2.54 | 3.331 (2) | 143 |
C15—H15B···O3 | 0.96 | 2.49 | 3.035 (3) | 116 |
C18—H18B···N3iv | 0.97 | 2.33 | 3.228 (3) | 154 |
Symmetry codes: (i) x, y−1, z; (ii) −x+1, −y, −z+1; (iii) −x+1, −y+1, −z+1; (iv) x, y+1, z. |