Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536802010255/ci6118sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536802010255/ci6118Isup2.hkl |
CCDC reference: 193728
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.004 Å
- R factor = 0.046
- wR factor = 0.122
- Data-to-parameter ratio = 12.8
checkCIF results
No syntax errors found ADDSYM reports no extra symmetry
Data collection: CAD-4 EXPRESS (Enraf-Nonius, 1994); cell refinement: CAD-4 EXPRESS; data reduction: MolEN (Fair, 1990); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: SHELXL97.
C11H12N2O4 | Z = 4 |
Mr = 236.23 | F(000) = 496 |
Triclinic, P1 | Dx = 1.388 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 8.105 (3) Å | Cell parameters from 25 reflections |
b = 11.065 (2) Å | θ = 8.4–11.0° |
c = 14.163 (4) Å | µ = 0.11 mm−1 |
α = 111.17 (3)° | T = 293 K |
β = 95.85 (4)° | Elongated needle, clear light yellow |
γ = 102.97 (3)° | 0.33 × 0.25 × 0.05 mm |
V = 1130.6 (6) Å3 |
Enraf-Nonius CAD-4 diffractometer | Rint = 0.042 |
Radiation source: fine-focus sealed tube | θmax = 25.0°, θmin = 2.0° |
Graphite monochromator | h = 0→9 |
ω–2θ scans | k = −13→12 |
4142 measured reflections | l = −16→16 |
3962 independent reflections | 3 standard reflections every 50 reflections |
2114 reflections with I > 2σ(I) | intensity decay: 0.0% |
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)] = 0.046 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.122 | H-atom parameters constrained |
S = 0.88 | w = 1/[σ2(Fo2) + (0.0719P)2] where P = (Fo2 + 2Fc2)/3 |
3962 reflections | (Δ/σ)max < 0.001 |
309 parameters | Δρmax = 0.18 e Å−3 |
0 restraints | Δρmin = −0.13 e Å−3 |
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. |
x | y | z | Uiso*/Ueq | ||
O1 | 0.37034 (19) | −0.00055 (15) | 0.66001 (12) | 0.0661 (4) | |
O2 | 0.2691 (2) | 0.20041 (17) | 0.50280 (13) | 0.0758 (5) | |
O3 | 0.1358 (2) | 0.31415 (18) | 0.43816 (13) | 0.0833 (5) | |
H3O | 0.0449 | 0.3350 | 0.4395 | 0.125* | |
O4 | −0.1577 (2) | 0.33469 (17) | 0.48138 (13) | 0.0758 (5) | |
N1 | 0.1271 (2) | 0.11462 (15) | 0.63415 (12) | 0.0490 (4) | |
H1N | 0.2136 | 0.1201 | 0.6039 | 0.059* | |
N2 | −0.0001 (2) | 0.16030 (16) | 0.61250 (12) | 0.0479 (4) | |
C1 | 0.1218 (3) | 0.05626 (19) | 0.70745 (15) | 0.0491 (5) | |
C2 | 0.2501 (3) | −0.0054 (2) | 0.72026 (16) | 0.0517 (5) | |
C3 | 0.2467 (3) | −0.0654 (2) | 0.79047 (18) | 0.0628 (6) | |
H3 | 0.3314 | −0.1069 | 0.7996 | 0.075* | |
C4 | 0.1183 (3) | −0.0639 (2) | 0.84700 (19) | 0.0699 (7) | |
H4 | 0.1157 | −0.1055 | 0.8935 | 0.084* | |
C5 | −0.0066 (3) | −0.0010 (2) | 0.83513 (18) | 0.0677 (7) | |
H5 | −0.0924 | 0.0002 | 0.8740 | 0.081* | |
C6 | −0.0046 (3) | 0.0596 (2) | 0.76637 (17) | 0.0583 (6) | |
H6 | −0.0880 | 0.1029 | 0.7592 | 0.070* | |
C7 | 0.0015 (2) | 0.22091 (19) | 0.54830 (15) | 0.0468 (5) | |
C8 | 0.1456 (3) | 0.2438 (2) | 0.49468 (17) | 0.0597 (6) | |
C9 | −0.1499 (3) | 0.2692 (2) | 0.53534 (16) | 0.0559 (6) | |
C10 | −0.2947 (3) | 0.2370 (3) | 0.58675 (19) | 0.0746 (7) | |
H10A | −0.3868 | 0.2703 | 0.5675 | 0.112* | |
H10B | −0.2548 | 0.2791 | 0.6604 | 0.112* | |
H10C | −0.3359 | 0.1409 | 0.5656 | 0.112* | |
C11 | 0.5090 (3) | −0.0582 (2) | 0.6730 (2) | 0.0762 (7) | |
H11A | 0.5842 | −0.0484 | 0.6265 | 0.114* | |
H11B | 0.4621 | −0.1523 | 0.6583 | 0.114* | |
H11C | 0.5730 | −0.0124 | 0.7429 | 0.114* | |
O1' | 0.5158 (2) | 0.51711 (17) | 0.28300 (13) | 0.0788 (5) | |
O2' | 0.3233 (2) | 0.7098 (2) | 0.14893 (15) | 0.0945 (6) | |
O3' | 0.2915 (3) | 0.8208 (2) | 0.05051 (15) | 0.1104 (7) | |
H3'O | 0.3392 | 0.8399 | 0.0074 | 0.166* | |
O4' | 0.5048 (3) | 0.83538 (18) | −0.06765 (14) | 0.0980 (6) | |
N1' | 0.5984 (2) | 0.62061 (16) | 0.14815 (13) | 0.0570 (5) | |
H1'N | 0.5093 | 0.6293 | 0.1752 | 0.068* | |
N2' | 0.6277 (2) | 0.66395 (16) | 0.07590 (13) | 0.0533 (5) | |
C1' | 0.7133 (3) | 0.5592 (2) | 0.18197 (16) | 0.0559 (6) | |
C2' | 0.6687 (3) | 0.5049 (2) | 0.25389 (18) | 0.0633 (6) | |
C3' | 0.7770 (4) | 0.4421 (2) | 0.2874 (2) | 0.0787 (8) | |
H3' | 0.7486 | 0.4044 | 0.3346 | 0.094* | |
C4' | 0.9271 (4) | 0.4353 (3) | 0.2509 (2) | 0.0881 (9) | |
H4' | 0.9992 | 0.3925 | 0.2735 | 0.106* | |
C5' | 0.9715 (4) | 0.4907 (3) | 0.1818 (2) | 0.0857 (8) | |
H5' | 1.0739 | 0.4863 | 0.1583 | 0.103* | |
C6' | 0.8645 (3) | 0.5531 (2) | 0.14681 (19) | 0.0704 (7) | |
H6' | 0.8944 | 0.5908 | 0.0998 | 0.085* | |
C7' | 0.5276 (3) | 0.7248 (2) | 0.04380 (16) | 0.0561 (6) | |
C8' | 0.3735 (3) | 0.7500 (3) | 0.0852 (2) | 0.0740 (7) | |
C9' | 0.5841 (3) | 0.7712 (2) | −0.03530 (17) | 0.0669 (7) | |
C10' | 0.7367 (4) | 0.7383 (3) | −0.0766 (2) | 0.0846 (8) | |
H10D | 0.7515 | 0.7683 | −0.1317 | 0.127* | |
H10E | 0.7194 | 0.6425 | −0.1023 | 0.127* | |
H10F | 0.8380 | 0.7830 | −0.0225 | 0.127* | |
C11' | 0.4609 (4) | 0.4578 (3) | 0.3535 (2) | 0.1015 (10) | |
H11D | 0.3524 | 0.4730 | 0.3680 | 0.152* | |
H11E | 0.5460 | 0.4982 | 0.4166 | 0.152* | |
H11F | 0.4476 | 0.3624 | 0.3231 | 0.152* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0603 (9) | 0.0762 (11) | 0.0852 (11) | 0.0387 (8) | 0.0227 (8) | 0.0448 (9) |
O2 | 0.0603 (10) | 0.1012 (13) | 0.0879 (12) | 0.0366 (10) | 0.0281 (9) | 0.0505 (11) |
O3 | 0.0780 (12) | 0.1078 (14) | 0.0968 (13) | 0.0299 (10) | 0.0299 (10) | 0.0720 (12) |
O4 | 0.0805 (11) | 0.0900 (12) | 0.0879 (12) | 0.0397 (9) | 0.0154 (9) | 0.0614 (11) |
N1 | 0.0462 (10) | 0.0523 (10) | 0.0587 (11) | 0.0233 (8) | 0.0120 (8) | 0.0274 (9) |
N2 | 0.0494 (10) | 0.0480 (10) | 0.0522 (10) | 0.0220 (8) | 0.0089 (8) | 0.0219 (9) |
C1 | 0.0519 (12) | 0.0428 (12) | 0.0538 (13) | 0.0147 (10) | 0.0016 (10) | 0.0221 (11) |
C2 | 0.0503 (12) | 0.0485 (12) | 0.0589 (14) | 0.0194 (10) | 0.0066 (11) | 0.0221 (11) |
C3 | 0.0675 (15) | 0.0599 (14) | 0.0718 (16) | 0.0300 (12) | 0.0062 (12) | 0.0332 (13) |
C4 | 0.0815 (18) | 0.0740 (17) | 0.0719 (16) | 0.0293 (14) | 0.0131 (14) | 0.0452 (14) |
C5 | 0.0687 (15) | 0.0807 (17) | 0.0756 (16) | 0.0330 (13) | 0.0234 (13) | 0.0462 (15) |
C6 | 0.0560 (13) | 0.0642 (14) | 0.0659 (15) | 0.0286 (11) | 0.0109 (11) | 0.0318 (13) |
C7 | 0.0501 (12) | 0.0459 (12) | 0.0478 (12) | 0.0167 (10) | 0.0079 (10) | 0.0208 (11) |
C8 | 0.0555 (14) | 0.0643 (15) | 0.0622 (15) | 0.0165 (12) | 0.0093 (11) | 0.0291 (13) |
C9 | 0.0586 (13) | 0.0608 (14) | 0.0552 (13) | 0.0251 (11) | 0.0065 (11) | 0.0270 (12) |
C10 | 0.0594 (14) | 0.108 (2) | 0.0856 (18) | 0.0463 (14) | 0.0231 (13) | 0.0558 (16) |
C11 | 0.0611 (15) | 0.0851 (18) | 0.099 (2) | 0.0422 (13) | 0.0178 (13) | 0.0417 (16) |
O1' | 0.0853 (12) | 0.0904 (13) | 0.0804 (12) | 0.0193 (10) | 0.0200 (10) | 0.0583 (11) |
O2' | 0.0907 (13) | 0.1254 (16) | 0.0956 (14) | 0.0535 (12) | 0.0373 (11) | 0.0571 (13) |
O3' | 0.1262 (17) | 0.1416 (18) | 0.1036 (15) | 0.0908 (15) | 0.0272 (13) | 0.0614 (14) |
O4' | 0.1442 (18) | 0.0932 (14) | 0.0799 (13) | 0.0532 (13) | 0.0088 (11) | 0.0526 (12) |
N1' | 0.0687 (12) | 0.0561 (11) | 0.0580 (11) | 0.0226 (9) | 0.0142 (9) | 0.0327 (10) |
N2' | 0.0682 (12) | 0.0469 (10) | 0.0491 (10) | 0.0175 (9) | 0.0108 (9) | 0.0233 (9) |
C1' | 0.0712 (15) | 0.0439 (12) | 0.0525 (13) | 0.0176 (11) | 0.0025 (11) | 0.0208 (11) |
C2' | 0.0771 (17) | 0.0495 (13) | 0.0593 (14) | 0.0088 (12) | −0.0045 (13) | 0.0272 (12) |
C3' | 0.096 (2) | 0.0599 (16) | 0.0784 (18) | 0.0115 (15) | −0.0118 (16) | 0.0392 (14) |
C4' | 0.099 (2) | 0.0660 (17) | 0.100 (2) | 0.0333 (16) | −0.0077 (18) | 0.0356 (17) |
C5' | 0.0867 (19) | 0.0826 (19) | 0.098 (2) | 0.0444 (16) | 0.0153 (16) | 0.0363 (18) |
C6' | 0.0832 (18) | 0.0652 (16) | 0.0755 (17) | 0.0321 (14) | 0.0191 (14) | 0.0347 (14) |
C7' | 0.0708 (15) | 0.0524 (13) | 0.0510 (13) | 0.0250 (12) | 0.0091 (11) | 0.0234 (11) |
C8' | 0.0887 (19) | 0.0788 (18) | 0.0644 (16) | 0.0383 (15) | 0.0117 (15) | 0.0319 (15) |
C9' | 0.0996 (19) | 0.0524 (14) | 0.0513 (14) | 0.0221 (13) | 0.0033 (13) | 0.0265 (12) |
C10' | 0.103 (2) | 0.092 (2) | 0.0699 (17) | 0.0239 (17) | 0.0310 (16) | 0.0444 (16) |
C11' | 0.113 (2) | 0.118 (2) | 0.093 (2) | 0.0158 (19) | 0.0294 (18) | 0.072 (2) |
O1—C2 | 1.364 (3) | O1'—C2' | 1.365 (3) |
O1—C11 | 1.438 (2) | O1'—C11' | 1.435 (3) |
O2—C8 | 1.216 (3) | O2'—C8' | 1.209 (3) |
O3—C8 | 1.311 (3) | O3'—C8' | 1.319 (3) |
O3—H3O | 0.82 | O3'—H3'O | 0.82 |
O4—C9 | 1.234 (2) | O4'—C9' | 1.228 (3) |
N1—N2 | 1.302 (2) | N1'—N2' | 1.299 (2) |
N1—C1 | 1.406 (2) | N1'—C1' | 1.409 (3) |
N1—H1N | 0.86 | N1'—H1'N | 0.86 |
N2—C7 | 1.310 (2) | N2'—C7' | 1.308 (3) |
C1—C6 | 1.384 (3) | C1'—C6' | 1.375 (3) |
C1—C2 | 1.396 (3) | C1'—C2' | 1.396 (3) |
C2—C3 | 1.380 (3) | C2'—C3' | 1.380 (3) |
C3—C4 | 1.376 (3) | C3'—C4' | 1.376 (4) |
C3—H3 | 0.93 | C3'—H3' | 0.93 |
C4—C5 | 1.380 (3) | C4'—C5' | 1.367 (4) |
C4—H4 | 0.93 | C4'—H4' | 0.93 |
C5—C6 | 1.366 (3) | C5'—C6' | 1.379 (3) |
C5—H5 | 0.93 | C5'—H5' | 0.93 |
C6—H6 | 0.93 | C6'—H6' | 0.93 |
C7—C9 | 1.465 (3) | C7'—C9' | 1.464 (3) |
C7—C8 | 1.481 (3) | C7'—C8' | 1.473 (3) |
C9—C10 | 1.486 (3) | C9'—C10' | 1.483 (4) |
C10—H10A | 0.96 | C10'—H10D | 0.96 |
C10—H10B | 0.96 | C10'—H10E | 0.96 |
C10—H10C | 0.96 | C10'—H10F | 0.96 |
C11—H11A | 0.96 | C11'—H11D | 0.96 |
C11—H11B | 0.96 | C11'—H11E | 0.96 |
C11—H11C | 0.96 | C11'—H11F | 0.96 |
C2—O1—C11 | 117.62 (17) | C2'—O1'—C11' | 117.3 (2) |
C8—O3—H3O | 109.5 | C8'—O3'—H3'O | 109.5 |
N2—N1—C1 | 119.37 (17) | N2'—N1'—C1' | 119.73 (19) |
N2—N1—H1N | 120.3 | N2'—N1'—H1'N | 120.1 |
C1—N1—H1N | 120.3 | C1'—N1'—H1'N | 120.1 |
N1—N2—C7 | 121.97 (17) | N1'—N2'—C7' | 122.04 (19) |
C6—C1—C2 | 120.14 (19) | C6'—C1'—C2' | 120.6 (2) |
C6—C1—N1 | 122.01 (18) | C6'—C1'—N1' | 122.0 (2) |
C2—C1—N1 | 117.85 (19) | C2'—C1'—N1' | 117.4 (2) |
O1—C2—C3 | 125.39 (18) | O1'—C2'—C3' | 125.8 (2) |
O1—C2—C1 | 115.42 (18) | O1'—C2'—C1' | 115.3 (2) |
C3—C2—C1 | 119.2 (2) | C3'—C2'—C1' | 118.9 (3) |
C4—C3—C2 | 120.1 (2) | C4'—C3'—C2' | 120.0 (3) |
C4—C3—H3 | 120.0 | C4'—C3'—H3' | 120.0 |
C2—C3—H3 | 120.0 | C2'—C3'—H3' | 120.0 |
C3—C4—C5 | 120.4 (2) | C5'—C4'—C3' | 120.8 (2) |
C3—C4—H4 | 119.8 | C5'—C4'—H4' | 119.6 |
C5—C4—H4 | 119.8 | C3'—C4'—H4' | 119.6 |
C6—C5—C4 | 120.2 (2) | C4'—C5'—C6' | 120.1 (3) |
C6—C5—H5 | 119.9 | C4'—C5'—H5' | 120.0 |
C4—C5—H5 | 119.9 | C6'—C5'—H5' | 120.0 |
C5—C6—C1 | 119.9 (2) | C1'—C6'—C5' | 119.6 (2) |
C5—C6—H6 | 120.0 | C1'—C6'—H6' | 120.2 |
C1—C6—H6 | 120.0 | C5'—C6'—H6' | 120.2 |
N2—C7—C9 | 114.61 (18) | N2'—C7'—C9' | 114.5 (2) |
N2—C7—C8 | 123.68 (18) | N2'—C7'—C8' | 123.7 (2) |
C9—C7—C8 | 121.68 (18) | C9'—C7'—C8' | 121.8 (2) |
O2—C8—O3 | 120.9 (2) | O2'—C8'—O3' | 120.5 (3) |
O2—C8—C7 | 121.9 (2) | O2'—C8'—C7' | 122.5 (2) |
O3—C8—C7 | 117.2 (2) | O3'—C8'—C7' | 117.0 (2) |
O4—C9—C7 | 120.2 (2) | O4'—C9'—C7' | 120.2 (2) |
O4—C9—C10 | 120.52 (19) | O4'—C9'—C10' | 120.5 (2) |
C7—C9—C10 | 119.24 (18) | C7'—C9'—C10' | 119.2 (2) |
C9—C10—H10A | 109.5 | C9'—C10'—H10D | 109.5 |
C9—C10—H10B | 109.5 | C9'—C10'—H10E | 109.5 |
H10A—C10—H10B | 109.5 | H10D—C10'—H10E | 109.5 |
C9—C10—H10C | 109.5 | C9'—C10'—H10F | 109.5 |
H10A—C10—H10C | 109.5 | H10D—C10'—H10F | 109.5 |
H10B—C10—H10C | 109.5 | H10E—C10'—H10F | 109.5 |
O1—C11—H11A | 109.5 | O1'—C11'—H11D | 109.5 |
O1—C11—H11B | 109.5 | O1'—C11'—H11E | 109.5 |
H11A—C11—H11B | 109.5 | H11D—C11'—H11E | 109.5 |
O1—C11—H11C | 109.5 | O1'—C11'—H11F | 109.5 |
H11A—C11—H11C | 109.5 | H11D—C11'—H11F | 109.5 |
H11B—C11—H11C | 109.5 | H11E—C11'—H11F | 109.5 |
C1—N1—N2—C7 | 176.95 (17) | C1'—N1'—N2'—C7' | −178.14 (19) |
N2—N1—C1—C6 | −7.6 (3) | N2'—N1'—C1'—C6' | 5.4 (3) |
N2—N1—C1—C2 | 172.86 (17) | N2'—N1'—C1'—C2' | −175.06 (19) |
C11—O1—C2—C3 | −2.4 (3) | C11'—O1'—C2'—C3' | −1.0 (3) |
C11—O1—C2—C1 | 177.75 (19) | C11'—O1'—C2'—C1' | 177.5 (2) |
C6—C1—C2—O1 | −178.67 (19) | C6'—C1'—C2'—O1' | 179.9 (2) |
N1—C1—C2—O1 | 0.9 (3) | N1'—C1'—C2'—O1' | 0.4 (3) |
C6—C1—C2—C3 | 1.5 (3) | C6'—C1'—C2'—C3' | −1.5 (3) |
N1—C1—C2—C3 | −179.01 (19) | N1'—C1'—C2'—C3' | 179.0 (2) |
O1—C2—C3—C4 | −180.0 (2) | O1'—C2'—C3'—C4' | 179.2 (2) |
C1—C2—C3—C4 | −0.1 (3) | C1'—C2'—C3'—C4' | 0.8 (4) |
C2—C3—C4—C5 | −0.9 (4) | C2'—C3'—C4'—C5' | 0.3 (4) |
C3—C4—C5—C6 | 0.5 (4) | C3'—C4'—C5'—C6' | −0.7 (4) |
C4—C5—C6—C1 | 0.9 (4) | C2'—C1'—C6'—C5' | 1.1 (3) |
C2—C1—C6—C5 | −1.8 (3) | N1'—C1'—C6'—C5' | −179.4 (2) |
N1—C1—C6—C5 | 178.6 (2) | C4'—C5'—C6'—C1' | 0.0 (4) |
N1—N2—C7—C9 | −178.31 (17) | N1'—N2'—C7'—C9' | 177.82 (18) |
N1—N2—C7—C8 | −0.1 (3) | N1'—N2'—C7'—C8' | −0.2 (3) |
N2—C7—C8—O2 | 4.2 (3) | N2'—C7'—C8'—O2' | −3.7 (4) |
C9—C7—C8—O2 | −177.8 (2) | C9'—C7'—C8'—O2' | 178.4 (3) |
N2—C7—C8—O3 | −175.3 (2) | N2'—C7'—C8'—O3' | 175.4 (2) |
C9—C7—C8—O3 | 2.7 (3) | C9'—C7'—C8'—O3' | −2.4 (3) |
N2—C7—C9—O4 | 175.8 (2) | N2'—C7'—C9'—O4' | −176.5 (2) |
C8—C7—C9—O4 | −2.4 (3) | C8'—C7'—C9'—O4' | 1.5 (4) |
N2—C7—C9—C10 | −5.0 (3) | N2'—C7'—C9'—C10' | 4.2 (3) |
C8—C7—C9—C10 | 176.8 (2) | C8'—C7'—C9'—C10' | −177.8 (2) |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1N···O2 | 0.86 | 1.98 | 2.628 (2) | 132 |
O3—H3O···O4 | 0.82 | 1.80 | 2.554 (2) | 152 |
N1′—H1′N···O2′ | 0.86 | 1.98 | 2.633 (3) | 132 |
O3′—H3′O···O4′ | 0.82 | 1.79 | 2.544 (3) | 152 |
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