Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807015735/hk2221sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807015735/hk2221Isup2.hkl |
CCDC reference: 651401
Key indicators
- Single-crystal X-ray study
- T = 294 K
- Mean (C-C) = 0.008 Å
- R factor = 0.069
- wR factor = 0.200
- Data-to-parameter ratio = 9.2
checkCIF/PLATON results
No syntax errors found
Alert level A PLAT035_ALERT_1_A No _chemical_absolute_configuration info given . ?
Alert level C DIFMN02_ALERT_2_C The minimum difference density is < -0.1*ZMAX*0.75 _refine_diff_density_min given = -0.673 Test value = -0.600 DIFMN03_ALERT_1_C The minimum difference density is < -0.1*ZMAX*0.75 The relevant atom site should be identified. DIFMX01_ALERT_2_C The maximum difference density is > 0.1*ZMAX*0.75 _refine_diff_density_max given = 0.612 Test value = 0.600 DIFMX02_ALERT_1_C The maximum difference density is > 0.1*ZMAX*0.75 The relevant atom site should be identified. PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ? PLAT097_ALERT_2_C Maximum (Positive) Residual Density ............ 0.61 e/A PLAT098_ALERT_2_C Minimum (Negative) Residual Density ............ -0.67 e/A PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 8 PLAT420_ALERT_2_C D-H Without Acceptor N1 - H1A ... ?
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 25.97 From the CIF: _reflns_number_total 1612 Count of symmetry unique reflns 1614 Completeness (_total/calc) 99.88% 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 PLAT200_ALERT_1_G Check the Reported _diffrn_ambient_temperature . 293 K PLAT791_ALERT_1_G Confirm the Absolute Configuration of C6 = . S
1 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 9 ALERT level C = Check and explain 3 ALERT level G = General alerts; check 6 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 1 ALERT type 3 Indicator that the structure quality may be low 1 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check
Data collection: CAD-4 Software (Enraf–Nonius, 1989); cell refinement: CAD-4 Software; 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 (Bruker, 2000); software used to prepare material for publication: SHELXTL.
C15H16N2O3 | F(000) = 576 |
Mr = 272.30 | Dx = 1.265 Mg m−3 |
Orthorhombic, P212121 | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: P 2ac 2ab | Cell parameters from 25 reflections |
a = 9.4220 (19) Å | θ = 9–13° |
b = 10.587 (2) Å | µ = 0.09 mm−1 |
c = 14.328 (3) Å | T = 294 K |
V = 1429.2 (5) Å3 | Block, colorless |
Z = 4 | 0.30 × 0.20 × 0.20 mm |
Enraf–Nonius CAD-4 diffractometer | 1211 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.021 |
Graphite monochromator | θmax = 26.0°, θmin = 2.4° |
ω/2θ scans | h = 0→11 |
Absorption correction: ψ scan (North et al., 1968) | k = 0→13 |
Tmin = 0.974, Tmax = 0.982 | l = 0→17 |
1634 measured reflections | 3 standard reflections every 120 min |
1612 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)] = 0.069 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.200 | H-atom parameters constrained |
S = 1.06 | w = 1/[σ2(Fo2) + (0.1P)2 + 1.3P] where P = (Fo2 + 2Fc2)/3 |
1612 reflections | (Δ/σ)max < 0.001 |
175 parameters | Δρmax = 0.61 e Å−3 |
1 restraint | Δρmin = −0.67 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 | ||
O1 | 0.8618 (4) | 0.8428 (4) | 0.6888 (3) | 0.0533 (11) | |
O2 | 0.9329 (4) | 0.5009 (4) | 0.8343 (3) | 0.0515 (11) | |
H2A | 0.9981 | 0.4515 | 0.8241 | 0.077* | |
O3 | 0.9733 (4) | 0.5619 (4) | 0.6880 (3) | 0.0465 (10) | |
N1 | 0.7147 (4) | 0.6787 (4) | 0.6775 (3) | 0.0383 (10) | |
H1A | 0.6527 | 0.6393 | 0.6445 | 0.046* | |
N2 | 0.2704 (5) | 0.6077 (5) | 0.7424 (4) | 0.0495 (13) | |
H2D | 0.1938 | 0.5974 | 0.7107 | 0.059* | |
C1 | 0.5920 (9) | 0.7664 (8) | 0.5107 (6) | 0.084 | |
H1B | 0.5643 | 0.8088 | 0.4544 | 0.125* | |
H1C | 0.5126 | 0.7628 | 0.5527 | 0.125* | |
H1D | 0.6226 | 0.6822 | 0.4962 | 0.125* | |
C2 | 0.7464 (9) | 0.9474 (6) | 0.5222 (5) | 0.0676 (19) | |
H2B | 0.6989 | 0.9817 | 0.4713 | 0.081* | |
H2C | 0.8204 | 0.9917 | 0.5501 | 0.081* | |
C3 | 0.7088 (7) | 0.8358 (6) | 0.5550 (5) | 0.0573 (17) | |
C4 | 0.7669 (5) | 0.7871 (5) | 0.6447 (4) | 0.0398 (13) | |
C5 | 0.8991 (5) | 0.5595 (5) | 0.7569 (4) | 0.0355 (12) | |
C6 | 0.7564 (5) | 0.6247 (5) | 0.7650 (4) | 0.0357 (12) | |
H6A | 0.7653 | 0.6931 | 0.8106 | 0.043* | |
C7 | 0.6414 (5) | 0.5319 (5) | 0.8001 (4) | 0.0413 (13) | |
H7A | 0.6486 | 0.4539 | 0.7649 | 0.050* | |
H7B | 0.6600 | 0.5122 | 0.8651 | 0.050* | |
C8 | 0.4940 (5) | 0.5816 (5) | 0.7915 (4) | 0.0381 (12) | |
C9 | 0.4304 (5) | 0.6838 (5) | 0.8436 (4) | 0.0368 (12) | |
C10 | 0.4757 (7) | 0.7634 (6) | 0.9155 (4) | 0.0467 (14) | |
H10A | 0.5675 | 0.7578 | 0.9390 | 0.056* | |
C11 | 0.3811 (9) | 0.8505 (7) | 0.9508 (4) | 0.0629 (19) | |
H11A | 0.4102 | 0.9047 | 0.9982 | 0.076* | |
C12 | 0.2438 (7) | 0.8590 (6) | 0.9174 (5) | 0.0545 (17) | |
H12A | 0.1830 | 0.9185 | 0.9434 | 0.065* | |
C13 | 0.1942 (6) | 0.7829 (5) | 0.8476 (4) | 0.0453 (14) | |
H13A | 0.1015 | 0.7889 | 0.8257 | 0.054* | |
C14 | 0.2909 (6) | 0.6954 (5) | 0.8108 (4) | 0.0380 (12) | |
C15 | 0.3931 (5) | 0.5387 (6) | 0.7326 (4) | 0.0447 (14) | |
H15A | 0.4048 | 0.4718 | 0.6913 | 0.054* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.050 (2) | 0.043 (2) | 0.067 (3) | −0.017 (2) | −0.006 (2) | 0.001 (2) |
O2 | 0.041 (2) | 0.070 (3) | 0.043 (2) | 0.022 (2) | −0.0005 (18) | 0.004 (2) |
O3 | 0.0281 (17) | 0.056 (2) | 0.056 (2) | −0.0003 (18) | 0.0033 (18) | 0.002 (2) |
N1 | 0.0240 (19) | 0.036 (2) | 0.055 (3) | −0.0072 (19) | −0.006 (2) | 0.004 (2) |
N2 | 0.025 (2) | 0.060 (3) | 0.063 (3) | −0.001 (2) | −0.006 (2) | −0.004 (3) |
C1 | 0.084 | 0.084 | 0.084 | 0.000 | 0.000 | 0.000 |
C2 | 0.088 (5) | 0.054 (4) | 0.061 (4) | −0.004 (4) | 0.000 (4) | 0.012 (4) |
C3 | 0.065 (4) | 0.055 (4) | 0.052 (3) | −0.012 (4) | −0.010 (3) | 0.011 (3) |
C4 | 0.027 (2) | 0.045 (3) | 0.047 (3) | −0.002 (2) | 0.001 (2) | 0.001 (3) |
C5 | 0.027 (2) | 0.036 (3) | 0.043 (3) | 0.000 (2) | 0.000 (2) | −0.004 (3) |
C6 | 0.026 (2) | 0.036 (3) | 0.046 (3) | 0.002 (2) | 0.003 (2) | 0.002 (2) |
C7 | 0.030 (2) | 0.041 (3) | 0.054 (3) | 0.003 (2) | 0.008 (3) | 0.004 (3) |
C8 | 0.027 (2) | 0.037 (3) | 0.050 (3) | 0.001 (2) | 0.004 (2) | 0.004 (3) |
C9 | 0.033 (2) | 0.038 (3) | 0.040 (3) | −0.002 (2) | 0.001 (2) | 0.009 (2) |
C10 | 0.045 (3) | 0.050 (3) | 0.045 (3) | 0.001 (3) | −0.003 (3) | −0.001 (3) |
C11 | 0.095 (6) | 0.054 (4) | 0.039 (3) | −0.005 (4) | −0.004 (4) | −0.006 (3) |
C12 | 0.058 (4) | 0.047 (3) | 0.059 (4) | 0.012 (3) | 0.020 (3) | 0.008 (3) |
C13 | 0.035 (3) | 0.042 (3) | 0.059 (4) | 0.006 (3) | 0.013 (3) | 0.009 (3) |
C14 | 0.031 (2) | 0.040 (3) | 0.044 (3) | −0.003 (2) | 0.003 (2) | 0.005 (3) |
C15 | 0.034 (3) | 0.044 (3) | 0.056 (3) | −0.005 (3) | 0.008 (3) | −0.008 (3) |
O1—C4 | 1.243 (6) | C6—C7 | 1.546 (7) |
O2—C5 | 1.309 (6) | C6—H6A | 0.9800 |
O2—H2A | 0.8200 | C7—C8 | 1.491 (7) |
O3—C5 | 1.210 (6) | C7—H7A | 0.9700 |
N1—C4 | 1.335 (7) | C7—H7B | 0.9700 |
N1—C6 | 1.433 (7) | C8—C15 | 1.350 (8) |
N1—H1A | 0.8600 | C8—C9 | 1.445 (7) |
N2—C14 | 1.364 (7) | C9—C10 | 1.398 (8) |
N2—C15 | 1.374 (7) | C9—C14 | 1.401 (7) |
N2—H2D | 0.8600 | C10—C11 | 1.379 (9) |
C1—C3 | 1.467 (8) | C10—H10A | 0.9300 |
C1—H1B | 0.9600 | C11—C12 | 1.382 (10) |
C1—H1C | 0.9600 | C11—H11A | 0.9300 |
C1—H1D | 0.9600 | C12—C13 | 1.367 (9) |
C2—C3 | 1.319 (8) | C12—H12A | 0.9300 |
C2—H2B | 0.9300 | C13—C14 | 1.402 (8) |
C2—H2C | 0.9300 | C13—H13A | 0.9300 |
C3—C4 | 1.490 (8) | C15—H15A | 0.9300 |
C5—C6 | 1.515 (7) | ||
C5—O2—H2A | 109.5 | C8—C7—C6 | 113.7 (4) |
C4—N1—C6 | 123.4 (5) | C8—C7—H7A | 108.8 |
C4—N1—H1A | 118.3 | C6—C7—H7A | 108.8 |
C6—N1—H1A | 118.3 | C8—C7—H7B | 108.8 |
C14—N2—C15 | 108.4 (5) | C6—C7—H7B | 108.8 |
C14—N2—H2D | 125.8 | H7A—C7—H7B | 107.7 |
C15—N2—H2D | 125.8 | C15—C8—C9 | 106.4 (5) |
C3—C1—H1B | 109.5 | C15—C8—C7 | 126.1 (5) |
C3—C1—H1C | 109.5 | C9—C8—C7 | 127.5 (5) |
H1B—C1—H1C | 109.5 | C10—C9—C14 | 118.7 (5) |
C3—C1—H1D | 109.5 | C10—C9—C8 | 134.9 (5) |
H1B—C1—H1D | 109.5 | C14—C9—C8 | 106.4 (5) |
H1C—C1—H1D | 109.5 | C11—C10—C9 | 118.4 (6) |
C3—C2—H2B | 120.0 | C11—C10—H10A | 120.8 |
C3—C2—H2C | 120.0 | C9—C10—H10A | 120.8 |
H2B—C2—H2C | 120.0 | C10—C11—C12 | 121.4 (6) |
C2—C3—C1 | 119.7 (7) | C10—C11—H11A | 119.3 |
C2—C3—C4 | 121.2 (6) | C12—C11—H11A | 119.3 |
C1—C3—C4 | 118.4 (6) | C13—C12—C11 | 122.4 (6) |
O1—C4—N1 | 119.6 (5) | C13—C12—H12A | 118.8 |
O1—C4—C3 | 122.6 (5) | C11—C12—H12A | 118.8 |
N1—C4—C3 | 117.8 (5) | C12—C13—C14 | 116.2 (6) |
O3—C5—O2 | 124.0 (4) | C12—C13—H13A | 121.9 |
O3—C5—C6 | 124.4 (5) | C14—C13—H13A | 121.9 |
O2—C5—C6 | 111.5 (4) | N2—C14—C9 | 108.3 (5) |
N1—C6—C5 | 111.1 (4) | N2—C14—C13 | 128.9 (5) |
N1—C6—C7 | 110.2 (4) | C9—C14—C13 | 122.8 (5) |
C5—C6—C7 | 110.9 (4) | C8—C15—N2 | 110.5 (5) |
N1—C6—H6A | 108.2 | C8—C15—H15A | 124.8 |
C5—C6—H6A | 108.2 | N2—C15—H15A | 124.8 |
C7—C6—H6A | 108.2 | ||
C6—N1—C4—O1 | 3.6 (8) | C15—C8—C9—C14 | −0.2 (6) |
C6—N1—C4—C3 | −177.0 (5) | C7—C8—C9—C14 | 179.9 (5) |
C2—C3—C4—O1 | −6.4 (10) | C14—C9—C10—C11 | −0.3 (8) |
C1—C3—C4—O1 | −177.0 (6) | C8—C9—C10—C11 | −178.0 (6) |
C2—C3—C4—N1 | 174.2 (6) | C9—C10—C11—C12 | 0.8 (9) |
C1—C3—C4—N1 | 3.6 (9) | C10—C11—C12—C13 | −0.5 (10) |
C4—N1—C6—C5 | −78.1 (6) | C11—C12—C13—C14 | −0.3 (9) |
C4—N1—C6—C7 | 158.5 (5) | C15—N2—C14—C9 | 1.5 (6) |
O3—C5—C6—N1 | 5.8 (7) | C15—N2—C14—C13 | −177.0 (6) |
O2—C5—C6—N1 | −174.8 (4) | C10—C9—C14—N2 | −179.1 (5) |
O3—C5—C6—C7 | 128.7 (6) | C8—C9—C14—N2 | −0.8 (6) |
O2—C5—C6—C7 | −51.9 (6) | C10—C9—C14—C13 | −0.5 (8) |
N1—C6—C7—C8 | −44.9 (6) | C8—C9—C14—C13 | 177.8 (5) |
C5—C6—C7—C8 | −168.3 (5) | C12—C13—C14—N2 | 179.1 (6) |
C6—C7—C8—C15 | 111.2 (6) | C12—C13—C14—C9 | 0.8 (8) |
C6—C7—C8—C9 | −68.9 (7) | C9—C8—C15—N2 | 1.1 (7) |
C15—C8—C9—C10 | 177.8 (6) | C7—C8—C15—N2 | −179.0 (5) |
C7—C8—C9—C10 | −2.1 (10) | C14—N2—C15—C8 | −1.6 (7) |
D—H···A | D—H | H···A | D···A | D—H···A |
O2—H2A···O1i | 0.82 | 1.76 | 2.580 (5) | 176 |
N2—H2D···O3ii | 0.86 | 2.14 | 2.946 (6) | 157 |
Symmetry codes: (i) −x+2, y−1/2, −z+3/2; (ii) x−1, y, z. |
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