Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805017496/bt6674sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536805017496/bt6674Isup2.hkl |
CCDC reference: 277202
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.008 Å
- R factor = 0.058
- wR factor = 0.189
- Data-to-parameter ratio = 6.2
checkCIF/PLATON results
No syntax errors found
Alert level B PLAT242_ALERT_2_B Check Low Ueq as Compared to Neighbors for N2
Alert level C ABSTM02_ALERT_3_C The ratio of expected to reported Tmax/Tmin(RR') is < 0.90 Tmin and Tmax reported: 0.846 0.993 Tmin' and Tmax expected: 0.965 0.973 RR' = 0.858 Please check that your absorption correction is appropriate. PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ? PLAT061_ALERT_3_C Tmax/Tmin Range Test RR' too Large ............. 0.86 PLAT062_ALERT_4_C Rescale T(min) & T(max) by ..................... 0.98 PLAT089_ALERT_3_C Poor Data / Parameter Ratio (Zmax .LT. 18) ..... 6.17 PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given ....... ? PLAT150_ALERT_1_C Volume as Calculated Differs from that Given ... 417.50 Ang-3 PLAT199_ALERT_1_C Check the Reported _cell_measurement_temperature 293 K PLAT200_ALERT_1_C Check the Reported _diffrn_ambient_temperature . 293 K PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for N1 PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 8
Alert level G FORMU01_ALERT_1_G There is a discrepancy between the atom counts in the _chemical_formula_sum and _chemical_formula_moiety. This is usually due to the moiety formula being in the wrong format. Atom count from _chemical_formula_sum: C4 H9 N3 O6 Atom count from _chemical_formula_moiety:C4 H9 N2 O2 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 25.00 From the CIF: _reflns_number_total 1474 Count of symmetry unique reflns 1484 Completeness (_total/calc) 99.33% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 0 Fraction of Friedel pairs measured 0.000 Are heavy atom types Z>Si present no
0 ALERT level A = In general: serious problem 1 ALERT level B = Potentially serious problem 11 ALERT level C = Check and explain 2 ALERT level G = General alerts; check 5 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 2 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 3 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: CAD-4 EXPRESS (Enraf–Nonius, (1994); cell refinement: CAD-4 EXPRESS; data reduction: XCAD4 (Harms & Wocadlo, 1995); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL/PC (Bruker, 2000); software used to prepare material for publication: SHELXL97.
C4H9NO3+NO3− | Z = 2 |
Mr = 195.14 | F(000) = 204 |
Triclinic, P1 | Dx = 1.552 Mg m−3 Dm = 1.545 Mg m−3 Dm measured by Flotation using a liquid mixture of xylene and CCl4 |
a = 5.357 (2) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 8.232 (3) Å | Cell parameters from 25 reflections |
c = 10.172 (4) Å | θ = 9.8–14.0° |
α = 96.88 (3)° | µ = 0.15 mm−1 |
β = 104.47 (3)° | T = 293 K |
γ = 102.11 (3)° | Block, colorless |
V = 417.5 (3) Å3 | 0.24 × 0.21 × 0.19 mm |
Nonius MACH3 sealed-tube diffractometer | 1358 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.057 |
Graphite monochromator | θmax = 25.0°, θmin = 2.1° |
ω–2θ scans | h = −1→6 |
Absorption correction: ψ scan (North et al., 1968) | k = −9→9 |
Tmin = 0.846, Tmax = 0.993 | l = −12→12 |
1988 measured reflections | 3 standard reflections every 60 min |
1474 independent reflections | intensity decay: none |
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)] = 0.058 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.189 | H-atom parameters constrained |
S = 1.13 | w = 1/[σ2(Fo2) + (0.1565P)2 + 0.0806P] where P = (Fo2 + 2Fc2)/3 |
1474 reflections | (Δ/σ)max < 0.001 |
239 parameters | Δρmax = 0.39 e Å−3 |
3 restraints | Δρmin = −0.42 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. 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 | ||
O1A | 0.4194 (11) | 0.5897 (7) | 0.2028 (5) | 0.0559 (13) | |
O1B | 0.5712 (10) | 0.4086 (6) | 0.3287 (5) | 0.0463 (11) | |
H1B | 0.6496 | 0.3945 | 0.2702 | 0.069* | |
C11 | 0.4456 (11) | 0.5254 (7) | 0.3041 (6) | 0.0350 (12) | |
C12 | 0.3249 (10) | 0.5801 (7) | 0.4178 (5) | 0.0308 (11) | |
H12 | 0.1308 | 0.5504 | 0.3797 | 0.037* | |
N11 | 0.3933 (10) | 0.4922 (6) | 0.5355 (5) | 0.0376 (11) | |
H11A | 0.3179 | 0.3821 | 0.5085 | 0.056* | |
H11B | 0.3339 | 0.5330 | 0.6036 | 0.056* | |
H11C | 0.5693 | 0.5088 | 0.5654 | 0.056* | |
C13 | 0.4199 (13) | 0.7707 (7) | 0.4688 (6) | 0.0403 (13) | |
H13A | 0.3643 | 0.8000 | 0.5504 | 0.048* | |
H13B | 0.6128 | 0.8043 | 0.4943 | 0.048* | |
C14 | 0.3085 (12) | 0.8651 (7) | 0.3593 (6) | 0.0361 (12) | |
N12 | 0.4745 (12) | 0.9956 (7) | 0.3397 (7) | 0.0517 (14) | |
H12A | 0.4182 | 1.0551 | 0.2801 | 0.062* | |
H12B | 0.6396 | 1.0217 | 0.3865 | 0.062* | |
O1C | 0.0656 (9) | 0.8199 (5) | 0.2948 (5) | 0.0448 (10) | |
O2A | 1.2159 (9) | 0.0990 (6) | 0.0883 (5) | 0.0445 (10) | |
O2B | 0.8322 (8) | −0.0600 (5) | 0.1003 (4) | 0.0407 (10) | |
H2B | 0.9297 | −0.0870 | 0.1655 | 0.061* | |
C21 | 0.9722 (10) | 0.0451 (7) | 0.0484 (6) | 0.0317 (11) | |
C22 | 0.8178 (11) | 0.1016 (7) | −0.0781 (5) | 0.0327 (11) | |
H22 | 0.8596 | 0.0483 | −0.1586 | 0.039* | |
N21 | 0.5250 (8) | 0.0396 (6) | −0.0997 (5) | 0.0330 (10) | |
H21A | 0.4799 | −0.0729 | −0.1166 | 0.049* | |
H21B | 0.4373 | 0.0775 | −0.1711 | 0.049* | |
H21C | 0.4836 | 0.0772 | −0.0241 | 0.049* | |
C23 | 0.8961 (11) | 0.2915 (7) | −0.0711 (6) | 0.0347 (12) | |
H23A | 1.0884 | 0.3300 | −0.0481 | 0.042* | |
H23B | 0.8213 | 0.3177 | −0.1609 | 0.042* | |
C24 | 0.7988 (10) | 0.3838 (7) | 0.0352 (5) | 0.0326 (11) | |
N22 | 0.7249 (14) | 0.5211 (7) | 0.0108 (6) | 0.0539 (15) | |
H22A | 0.6644 | 0.5743 | 0.0689 | 0.065* | |
H22B | 0.7368 | 0.5585 | −0.0635 | 0.065* | |
O2C | 0.7869 (8) | 0.3224 (5) | 0.1410 (4) | 0.0404 (9) | |
N1 | 0.0736 (11) | 0.6568 (6) | 0.7532 (6) | 0.0426 (12) | |
O11 | −0.0424 (13) | 0.7235 (7) | 0.8224 (7) | 0.0675 (16) | |
O12 | 0.3269 (10) | 0.6938 (7) | 0.7840 (5) | 0.0546 (12) | |
O13 | −0.0453 (11) | 0.5465 (8) | 0.6486 (7) | 0.0731 (18) | |
N2 | 0.1374 (10) | 0.1223 (6) | 0.6035 (6) | 0.0416 (12) | |
O21 | 0.0278 (13) | −0.0039 (7) | 0.6398 (6) | 0.0695 (16) | |
O22 | 0.3511 (14) | 0.2098 (9) | 0.6821 (8) | 0.100 (3) | |
O23 | 0.0439 (10) | 0.1644 (7) | 0.4930 (5) | 0.0556 (13) |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1A | 0.077 (3) | 0.070 (3) | 0.041 (2) | 0.039 (3) | 0.028 (2) | 0.027 (2) |
O1B | 0.063 (3) | 0.052 (2) | 0.038 (2) | 0.030 (2) | 0.024 (2) | 0.0162 (18) |
C11 | 0.034 (3) | 0.034 (3) | 0.035 (3) | 0.006 (2) | 0.007 (2) | 0.008 (2) |
C12 | 0.024 (2) | 0.036 (3) | 0.031 (2) | 0.0072 (19) | 0.004 (2) | 0.0092 (19) |
N11 | 0.046 (3) | 0.039 (2) | 0.035 (2) | 0.017 (2) | 0.016 (2) | 0.0141 (19) |
C13 | 0.050 (3) | 0.035 (3) | 0.032 (3) | 0.012 (2) | 0.005 (2) | 0.007 (2) |
C14 | 0.038 (3) | 0.034 (3) | 0.033 (3) | 0.010 (2) | 0.004 (2) | 0.008 (2) |
N12 | 0.039 (3) | 0.051 (3) | 0.056 (3) | 0.003 (2) | −0.004 (2) | 0.027 (3) |
O1C | 0.041 (2) | 0.044 (2) | 0.050 (2) | 0.0113 (18) | 0.0076 (19) | 0.0215 (19) |
O2A | 0.032 (2) | 0.057 (3) | 0.046 (2) | 0.0069 (18) | 0.0113 (17) | 0.018 (2) |
O2B | 0.034 (2) | 0.046 (2) | 0.042 (2) | 0.0066 (17) | 0.0075 (17) | 0.0209 (18) |
C21 | 0.026 (2) | 0.036 (2) | 0.034 (3) | 0.009 (2) | 0.008 (2) | 0.008 (2) |
C22 | 0.035 (3) | 0.036 (3) | 0.029 (2) | 0.008 (2) | 0.013 (2) | 0.008 (2) |
N21 | 0.024 (2) | 0.040 (2) | 0.033 (2) | 0.0046 (17) | 0.0062 (17) | 0.0080 (19) |
C23 | 0.035 (3) | 0.039 (3) | 0.032 (3) | 0.006 (2) | 0.012 (2) | 0.014 (2) |
C24 | 0.029 (2) | 0.034 (2) | 0.030 (3) | 0.001 (2) | 0.004 (2) | 0.0083 (19) |
N22 | 0.086 (5) | 0.042 (3) | 0.053 (3) | 0.025 (3) | 0.041 (3) | 0.021 (2) |
O2C | 0.046 (2) | 0.044 (2) | 0.039 (2) | 0.0141 (17) | 0.0207 (18) | 0.0128 (16) |
N1 | 0.051 (3) | 0.038 (2) | 0.045 (3) | 0.010 (2) | 0.023 (2) | 0.012 (2) |
O11 | 0.084 (4) | 0.064 (3) | 0.079 (4) | 0.025 (3) | 0.059 (3) | 0.022 (3) |
O12 | 0.042 (2) | 0.056 (3) | 0.057 (3) | 0.006 (2) | 0.008 (2) | 0.000 (2) |
O13 | 0.040 (3) | 0.079 (4) | 0.078 (4) | 0.000 (3) | 0.007 (3) | −0.022 (3) |
N2 | 0.039 (3) | 0.040 (2) | 0.041 (3) | 0.005 (2) | 0.005 (2) | 0.011 (2) |
O21 | 0.073 (4) | 0.055 (3) | 0.069 (3) | −0.010 (3) | 0.015 (3) | 0.024 (3) |
O22 | 0.068 (4) | 0.086 (4) | 0.097 (5) | −0.029 (3) | −0.043 (4) | 0.058 (4) |
O23 | 0.050 (3) | 0.056 (3) | 0.047 (3) | 0.006 (2) | −0.008 (2) | 0.017 (2) |
O1A—C11 | 1.205 (8) | C21—C22 | 1.526 (7) |
O1B—C11 | 1.298 (8) | C22—N21 | 1.494 (7) |
O1B—H1B | 0.8200 | C22—C23 | 1.520 (8) |
C11—C12 | 1.526 (8) | C22—H22 | 0.9800 |
C12—N11 | 1.481 (7) | N21—H21A | 0.8900 |
C12—C13 | 1.526 (8) | N21—H21B | 0.8900 |
C12—H12 | 0.9800 | N21—H21C | 0.8900 |
N11—H11A | 0.8900 | C23—C24 | 1.506 (8) |
N11—H11B | 0.8900 | C23—H23A | 0.9700 |
N11—H11C | 0.8900 | C23—H23B | 0.9700 |
C13—C14 | 1.507 (8) | C24—O2C | 1.252 (7) |
C13—H13A | 0.9700 | C24—N22 | 1.305 (8) |
C13—H13B | 0.9700 | N22—H22A | 0.8600 |
C14—O1C | 1.254 (8) | N22—H22B | 0.8600 |
C14—N12 | 1.313 (9) | N1—O11 | 1.205 (7) |
N12—H12A | 0.8600 | N1—O13 | 1.244 (8) |
N12—H12B | 0.8600 | N1—O12 | 1.274 (8) |
O2A—C21 | 1.230 (7) | N2—O21 | 1.227 (7) |
O2B—C21 | 1.275 (7) | N2—O23 | 1.232 (7) |
O2B—H2B | 0.8200 | N2—O22 | 1.236 (8) |
C11—O1B—H1B | 109.5 | O2B—C21—C22 | 115.4 (4) |
O1A—C11—O1B | 125.9 (6) | N21—C22—C23 | 111.0 (5) |
O1A—C11—C12 | 120.0 (5) | N21—C22—C21 | 110.3 (4) |
O1B—C11—C12 | 114.1 (5) | C23—C22—C21 | 113.0 (4) |
N11—C12—C11 | 111.1 (4) | N21—C22—H22 | 107.4 |
N11—C12—C13 | 109.4 (4) | C23—C22—H22 | 107.4 |
C11—C12—C13 | 111.0 (5) | C21—C22—H22 | 107.4 |
N11—C12—H12 | 108.4 | C22—N21—H21A | 109.5 |
C11—C12—H12 | 108.4 | C22—N21—H21B | 109.5 |
C13—C12—H12 | 108.4 | H21A—N21—H21B | 109.5 |
C12—N11—H11A | 109.5 | C22—N21—H21C | 109.5 |
C12—N11—H11B | 109.5 | H21A—N21—H21C | 109.5 |
H11A—N11—H11B | 109.5 | H21B—N21—H21C | 109.5 |
C12—N11—H11C | 109.5 | C24—C23—C22 | 111.5 (4) |
H11A—N11—H11C | 109.5 | C24—C23—H23A | 109.3 |
H11B—N11—H11C | 109.5 | C22—C23—H23A | 109.3 |
C14—C13—C12 | 111.2 (4) | C24—C23—H23B | 109.3 |
C14—C13—H13A | 109.4 | C22—C23—H23B | 109.3 |
C12—C13—H13A | 109.4 | H23A—C23—H23B | 108.0 |
C14—C13—H13B | 109.4 | O2C—C24—N22 | 123.3 (5) |
C12—C13—H13B | 109.4 | O2C—C24—C23 | 118.3 (5) |
H13A—C13—H13B | 108.0 | N22—C24—C23 | 118.4 (5) |
O1C—C14—N12 | 123.4 (5) | C24—N22—H22A | 120.0 |
O1C—C14—C13 | 119.7 (5) | C24—N22—H22B | 120.0 |
N12—C14—C13 | 116.9 (5) | H22A—N22—H22B | 120.0 |
C14—N12—H12A | 120.0 | O11—N1—O13 | 122.4 (6) |
C14—N12—H12B | 120.0 | O11—N1—O12 | 121.7 (6) |
H12A—N12—H12B | 120.0 | O13—N1—O12 | 115.9 (5) |
C21—O2B—H2B | 109.5 | O21—N2—O23 | 122.9 (5) |
O2A—C21—O2B | 126.1 (5) | O21—N2—O22 | 117.8 (6) |
O2A—C21—C22 | 118.5 (5) | O23—N2—O22 | 119.3 (5) |
O1A—C11—C12—N11 | −176.9 (6) | O2A—C21—C22—N21 | −173.3 (5) |
O1B—C11—C12—N11 | 3.2 (7) | O2B—C21—C22—N21 | 9.0 (6) |
O1A—C11—C12—C13 | −54.9 (7) | O2A—C21—C22—C23 | −48.3 (7) |
O1B—C11—C12—C13 | 125.2 (5) | O2B—C21—C22—C23 | 133.9 (5) |
N11—C12—C13—C14 | −168.9 (5) | N21—C22—C23—C24 | 53.5 (6) |
C11—C12—C13—C14 | 68.2 (6) | C21—C22—C23—C24 | −71.0 (6) |
C12—C13—C14—O1C | 46.8 (8) | C22—C23—C24—O2C | 32.7 (7) |
C12—C13—C14—N12 | −135.1 (6) | C22—C23—C24—N22 | −145.6 (6) |
D—H···A | D—H | H···A | D···A | D—H···A |
O1B—H1B···O2C | 0.82 | 1.76 | 2.570 (6) | 169 |
N11—H11A···O23 | 0.89 | 2.03 | 2.858 (7) | 155 |
N11—H11A···O22 | 0.89 | 2.39 | 2.908 (8) | 117 |
N11—H11B···O12 | 0.89 | 2.14 | 2.994 (7) | 159 |
N11—H11B···O13 | 0.89 | 2.21 | 2.951 (8) | 140 |
N11—H11C···O13i | 0.89 | 1.97 | 2.855 (8) | 175 |
N12—H12A···O2Aii | 0.86 | 2.09 | 2.903 (8) | 156 |
N12—H12B···O23iii | 0.86 | 2.17 | 2.998 (7) | 162 |
O2B—H2B···O1Civ | 0.82 | 1.69 | 2.490 (6) | 166 |
N21—H21A···O12v | 0.89 | 1.96 | 2.815 (7) | 161 |
N21—H21B···O22vi | 0.89 | 1.97 | 2.832 (8) | 162 |
N21—H21B···O21vi | 0.89 | 2.43 | 3.176 (8) | 141 |
N21—H21C···O2Avii | 0.89 | 2.07 | 2.887 (6) | 153 |
N21—H21C···O2C | 0.89 | 2.45 | 2.988 (6) | 120 |
N22—H22A···O1A | 0.86 | 2.13 | 2.921 (7) | 154 |
N22—H22B···O11viii | 0.86 | 2.23 | 3.014 (8) | 151 |
Symmetry codes: (i) x+1, y, z; (ii) x−1, y+1, z; (iii) x+1, y+1, z; (iv) x+1, y−1, z; (v) x, y−1, z−1; (vi) x, y, z−1; (vii) x−1, y, z; (viii) x+1, y, z−1. |
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