Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536804027965/ya6225sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536804027965/ya62253sup2.hkl |
CCDC reference: 259553
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.003 Å
- R factor = 0.040
- wR factor = 0.101
- Data-to-parameter ratio = 12.0
checkCIF/PLATON results
No syntax errors found
Alert level A PLAT220_ALERT_2_A Large Non-Solvent C Ueq(max)/Ueq(min) ... 5.48 Ratio PLAT241_ALERT_2_A Check High U(eq) as Compared to Neighbors for C10 PLAT242_ALERT_2_A Check Low U(eq) as Compared to Neighbors for C9
Alert level C PLAT026_ALERT_3_C Ratio Observed / Unique Reflections too Low .... 47 Perc. PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ? PLAT215_ALERT_3_C Disordered C10 has ADP max/min Ratio ....... 3.20 PLAT241_ALERT_2_C Check High U(eq) as Compared to Neighbors for C8 PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor .... 3.13 PLAT301_ALERT_3_C Main Residue Disorder ......................... 16.00 Perc. PLAT371_ALERT_2_C Long C(sp2)-C(sp1) Bond C5 - C7 ... 1.41 Ang.
3 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 7 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 6 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 0 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: P3 (Siemens,1989); cell refinement: P3; data reduction: XDISK (Siemens, 1991); program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX routine CIF_UPDATE (Farrugia, 1999).
C7H11N2+·C11H9N2O3− | F(000) = 360 |
Mr = 340.38 | Dx = 1.22 Mg m−3 |
Monoclinic, P21/m | Melting point: 414 K |
Hall symbol: -P 2yb | Mo Kα radiation, λ = 0.71073 Å |
a = 11.513 (3) Å | Cell parameters from 24 reflections |
b = 6.7830 (17) Å | θ = 11–13° |
c = 12.176 (3) Å | µ = 0.09 mm−1 |
β = 102.94 (2)° | T = 293 K |
V = 926.7 (4) Å3 | Needle, yellow |
Z = 2 | 0.4 × 0.1 × 0.1 mm |
Siemens P3/PC diffractometer | Rint = 0.097 |
Radiation source: fine-focus sealed tube | θmax = 26.1°, θmin = 2.8° |
Graphite monochromator | h = −14→13 |
θ–2θ scans | k = 0→8 |
2053 measured reflections | l = 0→15 |
1962 independent reflections | 2 standard reflections every 98 reflections |
916 reflections with I > 2σ(I) | intensity decay: 3% |
Refinement on F2 | 3 restraints |
Least-squares matrix: full | H-atom parameters constrained |
R[F2 > 2σ(F2)] = 0.040 | w = 1/[σ2(Fo2) + (0.0522P)2] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.101 | (Δ/σ)max = 0.004 |
S = 0.82 | Δρmax = 0.11 e Å−3 |
1962 reflections | Δρmin = −0.09 e Å−3 |
163 parameters |
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. |
x | y | z | Uiso*/Ueq | Occ. (<1) | |
O1 | 0.04301 (13) | 0.25 | 0.71435 (14) | 0.1384 (11) | |
O2 | −0.02009 (14) | 0.25 | 0.43758 (14) | 0.1318 (10) | |
O3 | 0.26312 (13) | 0.25 | 0.45191 (12) | 0.0974 (7) | |
N1 | 0.52749 (18) | 0.25 | 0.67206 (18) | 0.0871 (7) | |
N2 | 0.31703 (18) | 0.25 | 0.93482 (18) | 0.0986 (8) | |
N3 | 0.49110 (17) | 0.25 | 0.39996 (18) | 0.0776 (6) | |
H3N | 0.4503 | 0.25 | 0.4511 | 0.093* | |
N4 | 0.68525 (15) | 0.25 | 0.15751 (15) | 0.0722 (6) | |
C1 | 0.10021 (18) | 0.25 | 0.63430 (19) | 0.0873 (9) | |
C2 | 0.06976 (19) | 0.25 | 0.5123 (2) | 0.0973 (10) | |
C3 | 0.20091 (18) | 0.25 | 0.51960 (19) | 0.0733 (8) | |
C4 | 0.22288 (17) | 0.25 | 0.64159 (16) | 0.0630 (6) | |
C5 | 0.32583 (15) | 0.25 | 0.72704 (16) | 0.0584 (6) | |
C6 | 0.4371 (2) | 0.25 | 0.69918 (18) | 0.0614 (6) | |
C7 | 0.32092 (18) | 0.25 | 0.8421 (2) | 0.0687 (7) | |
C8 | −0.0876 (2) | 0.25 | 0.6795 (3) | 0.183 (2) | |
H8A | −0.1173 | 0.1166 | 0.6648 | 0.219* | 0.5 |
H8B | −0.1139 | 0.3277 | 0.6116 | 0.219* | 0.5 |
C9 | −0.1327 (4) | 0.3395 (12) | 0.7762 (5) | 0.175 (5) | 0.5 |
H9A | −0.2186 | 0.3544 | 0.7551 | 0.211* | 0.5 |
H9B | −0.0975 | 0.4687 | 0.7944 | 0.211* | 0.5 |
C10 | −0.0984 (5) | 0.2035 (15) | 0.8778 (5) | 0.301 (9) | 0.5 |
H10A | −0.1228 | 0.2625 | 0.9416 | 0.361* | 0.5 |
H10B | −0.0125 | 0.1878 | 0.8975 | 0.361* | 0.5 |
C11 | −0.1570 (10) | 0.0018 (15) | 0.8533 (15) | 0.320 (7) | 0.5 |
H11A | −0.1366 | −0.079 | 0.9196 | 0.48* | 0.5 |
H11B | −0.1294 | −0.06 | 0.793 | 0.48* | 0.5 |
H11C | −0.242 | 0.0174 | 0.832 | 0.48* | 0.5 |
C12 | 0.4358 (2) | 0.25 | 0.2922 (2) | 0.0762 (7) | |
H12 | 0.3529 | 0.25 | 0.273 | 0.091* | |
C13 | 0.49713 (18) | 0.25 | 0.20888 (19) | 0.0679 (6) | |
H13 | 0.4559 | 0.25 | 0.1339 | 0.082* | |
C14 | 0.62283 (17) | 0.25 | 0.23549 (18) | 0.0587 (6) | |
C15 | 0.67665 (19) | 0.25 | 0.35230 (18) | 0.0660 (6) | |
H15 | 0.7593 | 0.25 | 0.3754 | 0.079* | |
C16 | 0.6110 (2) | 0.25 | 0.42975 (19) | 0.0728 (7) | |
H16 | 0.6487 | 0.25 | 0.5057 | 0.087* | |
C17 | 0.6289 (2) | 0.25 | 0.03579 (18) | 0.0870 (8) | |
H17A | 0.6119 | 0.3832 | 0.0105 | 0.13* | 0.5 |
H17B | 0.556 | 0.1759 | 0.0231 | 0.13* | 0.5 |
H17C | 0.6821 | 0.1909 | −0.0052 | 0.13* | 0.5 |
C18 | 0.81543 (19) | 0.25 | 0.1853 (2) | 0.0982 (10) | |
H18A | 0.8439 | 0.3828 | 0.1985 | 0.147* | 0.5 |
H18B | 0.8441 | 0.1946 | 0.1238 | 0.147* | 0.5 |
H18C | 0.8438 | 0.1725 | 0.2519 | 0.147* | 0.5 |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0492 (9) | 0.294 (3) | 0.0700 (11) | 0 | 0.0085 (8) | 0 |
O2 | 0.0556 (9) | 0.248 (3) | 0.0769 (11) | 0 | −0.0179 (9) | 0 |
O3 | 0.0615 (10) | 0.166 (2) | 0.0627 (10) | 0 | 0.0105 (8) | 0 |
N1 | 0.0599 (12) | 0.0984 (19) | 0.0954 (16) | 0 | 0.0011 (11) | 0 |
N2 | 0.0912 (15) | 0.133 (2) | 0.0601 (13) | 0 | −0.0081 (11) | 0 |
N3 | 0.0715 (12) | 0.0898 (17) | 0.0770 (14) | 0 | 0.0284 (11) | 0 |
N4 | 0.0588 (10) | 0.1011 (17) | 0.0542 (12) | 0 | 0.0073 (9) | 0 |
C1 | 0.0462 (12) | 0.159 (3) | 0.0542 (14) | 0 | 0.0059 (10) | 0 |
C2 | 0.0524 (13) | 0.166 (3) | 0.0657 (16) | 0 | −0.0042 (12) | 0 |
C3 | 0.0486 (12) | 0.110 (2) | 0.0611 (15) | 0 | 0.0113 (11) | 0 |
C4 | 0.0492 (11) | 0.0838 (18) | 0.0500 (13) | 0 | −0.0020 (9) | 0 |
C5 | 0.0421 (10) | 0.0830 (17) | 0.0454 (13) | 0 | −0.0001 (8) | 0 |
C6 | 0.0545 (13) | 0.0579 (15) | 0.0619 (14) | 0 | −0.0079 (11) | 0 |
C7 | 0.0534 (12) | 0.0812 (19) | 0.0606 (16) | 0 | −0.0104 (10) | 0 |
C8 | 0.0488 (15) | 0.408 (8) | 0.090 (2) | 0 | 0.0147 (14) | 0 |
C9 | 0.064 (2) | 0.271 (16) | 0.194 (7) | 0.013 (4) | 0.034 (3) | −0.014 (6) |
C10 | 0.124 (4) | 0.69 (3) | 0.095 (4) | 0.141 (13) | 0.035 (3) | −0.011 (14) |
C11 | 0.257 (12) | 0.304 (17) | 0.357 (15) | −0.083 (10) | −0.018 (11) | −0.019 (12) |
C12 | 0.0530 (12) | 0.083 (2) | 0.0907 (19) | 0 | 0.0132 (13) | 0 |
C13 | 0.0587 (13) | 0.0727 (17) | 0.0662 (14) | 0 | 0.0008 (11) | 0 |
C14 | 0.0535 (12) | 0.0615 (15) | 0.0558 (13) | 0 | 0.0008 (10) | 0 |
C15 | 0.0559 (12) | 0.0816 (18) | 0.0600 (14) | 0 | 0.0117 (11) | 0 |
C16 | 0.0723 (15) | 0.0816 (19) | 0.0608 (14) | 0 | 0.0069 (12) | 0 |
C17 | 0.0775 (15) | 0.122 (2) | 0.0545 (14) | 0 | −0.0006 (11) | 0 |
C18 | 0.0537 (12) | 0.162 (3) | 0.0789 (17) | 0 | 0.0151 (11) | 0 |
O1—C1 | 1.293 (3) | C9—H9A | 0.97 |
O1—C8 | 1.468 (3) | C9—H9B | 0.97 |
O2—C2 | 1.215 (2) | C10—C11 | 1.525 (5) |
O3—C3 | 1.207 (2) | C10—H10A | 0.97 |
N1—C6 | 1.160 (3) | C10—H10B | 0.97 |
N2—C7 | 1.140 (3) | C11—H11A | 0.96 |
N3—C12 | 1.324 (3) | C11—H11B | 0.96 |
N3—C16 | 1.346 (3) | C11—H11C | 0.96 |
N3—H3N | 0.86 | C12—C13 | 1.360 (3) |
N4—C14 | 1.313 (2) | C12—H12 | 0.93 |
N4—C17 | 1.479 (3) | C13—C14 | 1.410 (3) |
N4—C18 | 1.461 (3) | C13—H13 | 0.93 |
C1—C2 | 1.448 (3) | C14—C15 | 1.418 (3) |
C1—C4 | 1.395 (3) | C15—C16 | 1.334 (3) |
C2—C3 | 1.493 (3) | C15—H15 | 0.93 |
C3—C4 | 1.450 (3) | C16—H16 | 0.93 |
C4—C5 | 1.391 (2) | C17—H17A | 0.96 |
C5—C6 | 1.396 (3) | C17—H17B | 0.96 |
C5—C7 | 1.414 (3) | C17—H17C | 0.96 |
C8—C9 | 1.515 (4) | C18—H18A | 0.96 |
C8—H8A | 0.97 | C18—H18B | 0.96 |
C8—H8B | 0.97 | C18—H18C | 0.96 |
C9—C10 | 1.523 (5) | ||
C1—O1—C8 | 116.37 (19) | C11—C10—H10A | 109.4 |
C12—N3—C16 | 120.2 (2) | C9—C10—H10B | 109.4 |
C12—N3—H3N | 119.9 | C11—C10—H10B | 109.4 |
C16—N3—H3N | 119.9 | H10A—C10—H10B | 108 |
C14—N4—C18 | 122.14 (18) | C10—C11—H11A | 109.5 |
C14—N4—C17 | 122.43 (17) | C10—C11—H11B | 109.5 |
C18—N4—C17 | 115.43 (19) | H11A—C11—H11B | 109.5 |
O1—C1—C4 | 129.1 (2) | C10—C11—H11C | 109.5 |
O1—C1—C2 | 136.58 (19) | H11A—C11—H11C | 109.5 |
C4—C1—C2 | 94.27 (18) | H11B—C11—H11C | 109.5 |
O2—C2—C1 | 137.6 (2) | N3—C12—C13 | 121.6 (2) |
O2—C2—C3 | 136.5 (2) | N3—C12—H12 | 119.2 |
C1—C2—C3 | 85.95 (17) | C13—C12—H12 | 119.2 |
O3—C3—C4 | 134.87 (18) | C12—C13—C14 | 120.4 (2) |
O3—C3—C2 | 134.9 (2) | C12—C13—H13 | 119.8 |
C4—C3—C2 | 90.19 (17) | C14—C13—H13 | 119.8 |
C5—C4—C1 | 136.8 (2) | N4—C14—C13 | 122.25 (19) |
C5—C4—C3 | 133.65 (18) | N4—C14—C15 | 122.57 (18) |
C1—C4—C3 | 89.59 (16) | C13—C14—C15 | 115.2 (2) |
C4—C5—C6 | 119.50 (18) | C16—C15—C14 | 121.3 (2) |
C4—C5—C7 | 121.63 (18) | C16—C15—H15 | 119.4 |
C6—C5—C7 | 118.87 (17) | C14—C15—H15 | 119.4 |
N1—C6—C5 | 177.6 (2) | C15—C16—N3 | 121.2 (2) |
N2—C7—C5 | 180.0 (2) | C15—C16—H16 | 119.4 |
O1—C8—C9 | 106.4 (2) | N3—C16—H16 | 119.4 |
O1—C8—H8A | 110.4 | N4—C17—H17A | 109.5 |
C9—C8—H8A | 110.4 | N4—C17—H17B | 109.5 |
O1—C8—H8B | 110.4 | H17A—C17—H17B | 109.5 |
C9—C8—H8B | 110.4 | N4—C17—H17C | 109.5 |
H8A—C8—H8B | 108.6 | H17A—C17—H17C | 109.5 |
C8—C9—C10 | 108.5 (5) | H17B—C17—H17C | 109.5 |
C8—C9—H9A | 110 | N4—C18—H18A | 109.5 |
C10—C9—H9A | 110 | N4—C18—H18B | 109.5 |
C8—C9—H9B | 110 | H18A—C18—H18B | 109.5 |
C10—C9—H9B | 110 | N4—C18—H18C | 109.5 |
H9A—C9—H9B | 108.4 | H18A—C18—H18C | 109.5 |
C9—C10—C11 | 111.2 (10) | H18B—C18—H18C | 109.5 |
C9—C10—H10A | 109.4 | ||
C8—O1—C1—C4 | 180 | C3—C4—C5—C6 | 0 |
C8—O1—C1—C2 | 0 | C1—C4—C5—C7 | 0 |
O1—C1—C2—O2 | 0 | C3—C4—C5—C7 | 180 |
C4—C1—C2—O2 | 180 | C1—O1—C8—C9 | −155.3 (3) |
O1—C1—C2—C3 | 180 | O1—C8—C9—C10 | −64.9 (5) |
C4—C1—C2—C3 | 0 | C8—C9—C10—C11 | −62.2 (7) |
O2—C2—C3—O3 | 0 | C16—N3—C12—C13 | 0 |
C1—C2—C3—O3 | 180 | N3—C12—C13—C14 | 0 |
O2—C2—C3—C4 | 180 | C18—N4—C14—C13 | 180 |
C1—C2—C3—C4 | 0 | C17—N4—C14—C13 | 0 |
O1—C1—C4—C5 | 0 | C18—N4—C14—C15 | 0 |
C2—C1—C4—C5 | 180 | C17—N4—C14—C15 | 180 |
O1—C1—C4—C3 | 180 | C12—C13—C14—N4 | 180 |
C2—C1—C4—C3 | 0 | C12—C13—C14—C15 | 0 |
O3—C3—C4—C5 | 0 | N4—C14—C15—C16 | 180 |
C2—C3—C4—C5 | 180 | C13—C14—C15—C16 | 0 |
O3—C3—C4—C1 | 180 | C14—C15—C16—N3 | 0 |
C2—C3—C4—C1 | 0 | C12—N3—C16—C15 | 0 |
C1—C4—C5—C6 | 180 |
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