Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805020751/wk6056sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536805020751/wk6056Isup2.hkl |
CCDC reference: 282686
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.003 Å
- R factor = 0.049
- wR factor = 0.126
- Data-to-parameter ratio = 10.8
checkCIF/PLATON results
No syntax errors found
Alert level C PLAT041_ALERT_1_C Calc. and Rep. SumFormula Strings Differ .... ? PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ? PLAT045_ALERT_1_C Calculated and Reported Z Differ by ............ 0.50 Ratio PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ? PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given ....... ? PLAT199_ALERT_1_C Check the Reported _cell_measurement_temperature 293 K PLAT200_ALERT_1_C Check the Reported _diffrn_ambient_temperature . 293 K PLAT708_ALERT_1_C D-H..A Calc 166.9(18), Rep 170(2), Dev.. 1.72 Sigma N2 -H1# -O1W 1.555 1.555 1.555 PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........ 2
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: C17 H15 N2 O2.5 Atom count from _chemical_formula_moiety:C17 H14.5 N2 O2
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 9 ALERT level C = Check and explain 1 ALERT level G = General alerts; check 8 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 0 ALERT type 2 Indicator that the structure model may be wrong or deficient 0 ALERT type 3 Indicator that the structure quality may be low 2 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 1997); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL, PARST (Nardelli, 1995) and PLATON (Spek, 1990).
C17H14N2O2·0.5H2O | F(000) = 1208 |
Mr = 287.31 | Dx = 1.358 Mg m−3 |
Monoclinic, C2/c | Mo Kα radiation, λ = 0.71073 Å |
a = 11.093 (5) Å | Cell parameters from 1582 reflections |
b = 12.944 (6) Å | θ = 2.4–21.7° |
c = 19.584 (9) Å | µ = 0.09 mm−1 |
β = 91.855 (9)° | T = 293 K |
V = 2811 (2) Å3 | Block, colourless |
Z = 8 | 0.39 × 0.17 × 0.12 mm |
Siemens SMART 1000 CCD area-detector diffractometer | 2766 independent reflections |
Radiation source: fine-focus sealed tube | 1883 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.029 |
Detector resolution: 8.33 pixels mm-1 | θmax = 26.1°, θmin = 2.1° |
ω scans | h = −13→10 |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | k = −14→15 |
Tmin = 0.965, Tmax = 0.989 | l = −24→23 |
7758 measured reflections |
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)] = 0.049 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.126 | All H-atom parameters refined |
S = 1.03 | w = 1/[σ2(Fo2) + (0.062P)2 + 0.2335P] where P = (Fo2 + 2Fc2)/3 |
2766 reflections | (Δ/σ)max < 0.001 |
255 parameters | Δρmax = 0.15 e Å−3 |
0 restraints | Δρmin = −0.17 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 | ||
O1W | 0.0000 | 1.01821 (15) | 0.2500 | 0.0585 (5) | |
O1 | 0.13697 (12) | 0.89327 (9) | 0.36658 (6) | 0.0527 (4) | |
O2 | 0.14888 (16) | 1.06758 (12) | 0.50525 (7) | 0.0795 (5) | |
N1 | 0.15193 (14) | 0.84257 (11) | 0.23408 (8) | 0.0488 (4) | |
N2 | 0.06612 (15) | 1.08829 (12) | 0.39837 (8) | 0.0492 (4) | |
C1 | 0.15754 (19) | 0.81575 (18) | 0.16915 (11) | 0.0567 (5) | |
C2 | 0.1724 (2) | 0.71403 (19) | 0.14687 (12) | 0.0639 (6) | |
C3 | 0.18212 (19) | 0.63771 (18) | 0.19347 (12) | 0.0605 (6) | |
C4 | 0.17733 (16) | 0.66081 (14) | 0.26357 (10) | 0.0496 (5) | |
C5 | 0.19014 (19) | 0.58500 (16) | 0.31514 (12) | 0.0615 (6) | |
C6 | 0.1862 (2) | 0.61225 (17) | 0.38170 (12) | 0.0655 (6) | |
C7 | 0.16743 (19) | 0.71525 (16) | 0.40080 (11) | 0.0574 (5) | |
C8 | 0.15475 (16) | 0.79088 (14) | 0.35243 (9) | 0.0455 (5) | |
C9 | 0.16032 (15) | 0.76566 (13) | 0.28174 (9) | 0.0431 (4) | |
C10 | 0.1429 (2) | 0.92028 (16) | 0.43708 (10) | 0.0568 (6) | |
C11 | 0.11983 (18) | 1.03325 (15) | 0.44883 (10) | 0.0520 (5) | |
C12 | 0.03680 (16) | 1.19466 (14) | 0.39950 (9) | 0.0467 (5) | |
C13 | −0.02384 (18) | 1.23503 (17) | 0.34282 (12) | 0.0584 (6) | |
C14 | −0.0520 (2) | 1.33895 (17) | 0.34006 (14) | 0.0662 (6) | |
C15 | −0.0210 (2) | 1.40323 (18) | 0.39349 (13) | 0.0678 (6) | |
C16 | 0.0377 (3) | 1.36274 (18) | 0.44936 (14) | 0.0790 (7) | |
C17 | 0.0676 (2) | 1.25963 (17) | 0.45317 (12) | 0.0708 (7) | |
H7 | 0.1674 (17) | 0.7301 (16) | 0.4493 (11) | 0.066 (6)* | |
H6 | 0.1950 (18) | 0.5601 (17) | 0.4164 (11) | 0.076 (7)* | |
H1N2 | 0.0493 (16) | 1.0584 (15) | 0.3595 (10) | 0.051 (6)* | |
H1 | 0.1519 (18) | 0.8738 (17) | 0.1374 (11) | 0.066 (6)* | |
H13 | −0.0470 (18) | 1.1907 (16) | 0.3057 (11) | 0.066 (6)* | |
H2 | 0.176 (2) | 0.7018 (18) | 0.1001 (13) | 0.085 (7)* | |
H15 | −0.037 (2) | 1.478 (2) | 0.3896 (11) | 0.086 (7)* | |
H3 | 0.1945 (19) | 0.5674 (18) | 0.1797 (11) | 0.077 (7)* | |
H1W1 | −0.064 (2) | 0.974 (2) | 0.2503 (14) | 0.110 (10)* | |
H10B | 0.224 (2) | 0.9031 (18) | 0.4550 (13) | 0.087 (8)* | |
H5 | 0.2012 (18) | 0.5108 (18) | 0.3012 (10) | 0.075 (6)* | |
H10A | 0.081 (2) | 0.8798 (19) | 0.4615 (12) | 0.086 (7)* | |
H14 | −0.092 (2) | 1.3645 (18) | 0.2993 (12) | 0.080 (7)* | |
H16 | 0.059 (2) | 1.408 (2) | 0.4856 (13) | 0.102 (9)* | |
H17 | 0.107 (2) | 1.2297 (18) | 0.4928 (13) | 0.085 (7)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1W | 0.0732 (15) | 0.0369 (11) | 0.0646 (13) | 0.000 | −0.0082 (11) | 0.000 |
O1 | 0.0768 (9) | 0.0396 (8) | 0.0415 (8) | 0.0090 (6) | −0.0024 (6) | −0.0013 (6) |
O2 | 0.1259 (14) | 0.0625 (10) | 0.0487 (9) | 0.0171 (9) | −0.0192 (9) | −0.0108 (7) |
N1 | 0.0552 (10) | 0.0464 (10) | 0.0447 (9) | 0.0025 (7) | −0.0021 (7) | 0.0030 (7) |
N2 | 0.0666 (11) | 0.0401 (9) | 0.0406 (9) | 0.0002 (7) | −0.0017 (8) | −0.0043 (7) |
C1 | 0.0629 (13) | 0.0612 (14) | 0.0458 (12) | 0.0024 (10) | −0.0007 (10) | 0.0019 (11) |
C2 | 0.0729 (15) | 0.0686 (16) | 0.0499 (13) | 0.0014 (11) | −0.0002 (11) | −0.0140 (12) |
C3 | 0.0642 (14) | 0.0509 (14) | 0.0659 (15) | 0.0014 (11) | −0.0032 (11) | −0.0148 (11) |
C4 | 0.0491 (11) | 0.0430 (11) | 0.0565 (12) | −0.0008 (8) | −0.0010 (9) | −0.0064 (9) |
C5 | 0.0745 (15) | 0.0364 (12) | 0.0733 (15) | 0.0038 (10) | −0.0024 (11) | −0.0012 (11) |
C6 | 0.0909 (17) | 0.0398 (13) | 0.0655 (15) | 0.0045 (11) | −0.0020 (12) | 0.0116 (11) |
C7 | 0.0765 (15) | 0.0460 (12) | 0.0496 (12) | 0.0056 (10) | −0.0015 (10) | 0.0058 (10) |
C8 | 0.0536 (11) | 0.0355 (10) | 0.0471 (11) | 0.0038 (8) | −0.0017 (8) | 0.0000 (8) |
C9 | 0.0414 (10) | 0.0388 (11) | 0.0489 (11) | 0.0008 (8) | −0.0008 (8) | 0.0002 (8) |
C10 | 0.0782 (16) | 0.0505 (13) | 0.0415 (12) | 0.0068 (11) | −0.0001 (11) | −0.0009 (9) |
C11 | 0.0680 (13) | 0.0457 (12) | 0.0423 (11) | 0.0031 (9) | 0.0014 (9) | −0.0022 (9) |
C12 | 0.0522 (12) | 0.0416 (11) | 0.0464 (11) | −0.0026 (8) | 0.0049 (9) | −0.0008 (8) |
C13 | 0.0634 (14) | 0.0488 (13) | 0.0623 (14) | −0.0010 (10) | −0.0088 (11) | −0.0055 (10) |
C14 | 0.0664 (15) | 0.0524 (14) | 0.0790 (17) | 0.0042 (11) | −0.0118 (12) | 0.0054 (12) |
C15 | 0.0751 (16) | 0.0419 (14) | 0.0863 (18) | 0.0022 (11) | −0.0003 (13) | −0.0006 (12) |
C16 | 0.119 (2) | 0.0452 (14) | 0.0716 (17) | 0.0017 (13) | −0.0083 (15) | −0.0136 (12) |
C17 | 0.111 (2) | 0.0483 (13) | 0.0518 (13) | 0.0063 (12) | −0.0120 (13) | −0.0073 (11) |
O1W—H1W1 | 0.91 (2) | C6—C7 | 1.402 (3) |
O1—C8 | 1.370 (2) | C6—H6 | 0.96 (2) |
O1—C10 | 1.424 (2) | C7—C8 | 1.366 (3) |
O2—C11 | 1.224 (2) | C7—H7 | 0.97 (2) |
N1—C1 | 1.322 (3) | C8—C9 | 1.426 (3) |
N1—C9 | 1.366 (2) | C10—C11 | 1.504 (3) |
N2—C11 | 1.342 (2) | C10—H10B | 0.99 (3) |
N2—C12 | 1.415 (2) | C10—H10A | 1.00 (2) |
N2—H1N2 | 0.87 (2) | C12—C17 | 1.380 (3) |
C1—C2 | 1.399 (3) | C12—C13 | 1.382 (3) |
C1—H1 | 0.98 (2) | C13—C14 | 1.382 (3) |
C2—C3 | 1.347 (3) | C13—H13 | 0.95 (2) |
C2—H2 | 0.93 (2) | C14—C15 | 1.372 (3) |
C3—C4 | 1.408 (3) | C14—H14 | 0.96 (2) |
C3—H3 | 0.96 (2) | C15—C16 | 1.360 (3) |
C4—C5 | 1.412 (3) | C15—H15 | 0.99 (2) |
C4—C9 | 1.417 (3) | C16—C17 | 1.377 (3) |
C5—C6 | 1.353 (3) | C16—H16 | 0.94 (3) |
C5—H5 | 1.01 (2) | C17—H17 | 0.96 (2) |
C8—O1—C10 | 115.56 (14) | N1—C9—C8 | 119.51 (16) |
C1—N1—C9 | 117.50 (17) | C4—C9—C8 | 118.25 (17) |
C11—N2—C12 | 127.00 (17) | O1—C10—C11 | 112.61 (16) |
C11—N2—H1N2 | 119.1 (13) | O1—C10—H10B | 107.7 (14) |
C12—N2—H1N2 | 113.8 (13) | C11—C10—H10B | 108.9 (14) |
N1—C1—C2 | 123.9 (2) | O1—C10—H10A | 108.9 (13) |
N1—C1—H1 | 114.0 (12) | C11—C10—H10A | 108.3 (14) |
C2—C1—H1 | 122.1 (12) | H10B—C10—H10A | 110.4 (19) |
C3—C2—C1 | 119.1 (2) | O2—C11—N2 | 124.71 (19) |
C3—C2—H2 | 122.4 (15) | O2—C11—C10 | 116.74 (18) |
C1—C2—H2 | 118.4 (15) | N2—C11—C10 | 118.51 (18) |
C2—C3—C4 | 120.0 (2) | C17—C12—C13 | 118.9 (2) |
C2—C3—H3 | 121.0 (14) | C17—C12—N2 | 123.59 (18) |
C4—C3—H3 | 119.0 (14) | C13—C12—N2 | 117.49 (17) |
C3—C4—C5 | 122.94 (19) | C14—C13—C12 | 120.2 (2) |
C3—C4—C9 | 117.24 (19) | C14—C13—H13 | 120.0 (12) |
C5—C4—C9 | 119.82 (19) | C12—C13—H13 | 119.7 (12) |
C6—C5—C4 | 120.2 (2) | C15—C14—C13 | 120.7 (2) |
C6—C5—H5 | 121.2 (12) | C15—C14—H14 | 121.5 (14) |
C4—C5—H5 | 118.7 (12) | C13—C14—H14 | 117.8 (14) |
C5—C6—C7 | 121.0 (2) | C16—C15—C14 | 118.8 (2) |
C5—C6—H6 | 119.5 (13) | C16—C15—H15 | 121.2 (13) |
C7—C6—H6 | 119.5 (13) | C14—C15—H15 | 119.9 (13) |
C8—C7—C6 | 120.6 (2) | C15—C16—C17 | 121.7 (2) |
C8—C7—H7 | 122.3 (12) | C15—C16—H16 | 118.1 (16) |
C6—C7—H7 | 117.1 (12) | C17—C16—H16 | 120.1 (16) |
C7—C8—O1 | 124.43 (18) | C16—C17—C12 | 119.7 (2) |
C7—C8—C9 | 120.16 (18) | C16—C17—H17 | 122.6 (15) |
O1—C8—C9 | 115.41 (15) | C12—C17—H17 | 117.6 (15) |
N1—C9—C4 | 122.23 (17) | ||
C9—N1—C1—C2 | −0.5 (3) | C7—C8—C9—N1 | −177.61 (17) |
N1—C1—C2—C3 | −0.2 (3) | O1—C8—C9—N1 | 2.1 (2) |
C1—C2—C3—C4 | −0.1 (3) | C7—C8—C9—C4 | 0.9 (3) |
C2—C3—C4—C5 | −178.2 (2) | O1—C8—C9—C4 | −179.36 (15) |
C2—C3—C4—C9 | 0.9 (3) | C8—O1—C10—C11 | −178.71 (17) |
C3—C4—C5—C6 | 179.2 (2) | C12—N2—C11—O2 | 2.2 (3) |
C9—C4—C5—C6 | 0.0 (3) | C12—N2—C11—C10 | 179.97 (18) |
C4—C5—C6—C7 | 1.0 (3) | O1—C10—C11—O2 | −164.36 (19) |
C5—C6—C7—C8 | −1.1 (3) | O1—C10—C11—N2 | 17.7 (3) |
C6—C7—C8—O1 | −179.57 (19) | C11—N2—C12—C17 | 4.4 (3) |
C6—C7—C8—C9 | 0.1 (3) | C11—N2—C12—C13 | −177.00 (19) |
C10—O1—C8—C7 | 5.5 (3) | C17—C12—C13—C14 | 0.5 (3) |
C10—O1—C8—C9 | −174.21 (17) | N2—C12—C13—C14 | −178.18 (19) |
C1—N1—C9—C4 | 1.5 (3) | C12—C13—C14—C15 | −0.4 (3) |
C1—N1—C9—C8 | 179.98 (17) | C13—C14—C15—C16 | −0.2 (4) |
C3—C4—C9—N1 | −1.7 (3) | C14—C15—C16—C17 | 0.7 (4) |
C5—C4—C9—N1 | 177.51 (17) | C15—C16—C17—C12 | −0.6 (4) |
C3—C4—C9—C8 | 179.79 (17) | C13—C12—C17—C16 | 0.0 (3) |
C5—C4—C9—C8 | −1.0 (3) | N2—C12—C17—C16 | 178.6 (2) |
D—H···A | D—H | H···A | D···A | D—H···A |
O1W—H1W1···N1i | 0.91 (2) | 1.99 (3) | 2.853 (3) | 157 (2) |
N2—H1N2···O1 | 0.87 (2) | 2.35 (2) | 2.722 (2) | 106 (2) |
N2—H1N2···O1W | 0.87 (2) | 2.26 (2) | 3.109 (2) | 170 (2) |
C13—H13···O1W | 0.95 (2) | 2.55 (2) | 3.359 (3) | 143 (2) |
C17—H17···O2 | 0.96 (2) | 2.16 (2) | 2.824 (3) | 125 (2) |
Symmetry code: (i) −x, y, −z+1/2. |
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