Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806054869/hg2155sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536806054869/hg2155Isup2.hkl |
CCDC reference: 636674
Key indicators
- Single-crystal X-ray study
- T = 293 K
- R factor = 0.022
- wR factor = 0.057
- Data-to-parameter ratio = 14.2
checkCIF/PLATON results
No syntax errors found No errors found in this datablock
Data collection: SMART (Bruker, 1997); cell refinement: SAINT (Bruker, 1997); data reduction: SAINT'; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1997); software used to prepare material for publication: SHELXTL.
C15H14N2O2FIS | F(000) = 848 |
Mr = 432.24 | Dx = 1.770 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
a = 8.7213 (17) Å | Cell parameters from 4524 reflections |
b = 12.530 (3) Å | θ = 1.4–27.9° |
c = 15.135 (3) Å | µ = 2.12 mm−1 |
β = 101.29 (3)° | T = 293 K |
V = 1622.0 (6) Å3 | Block, colorless |
Z = 4 | 0.22 × 0.20 × 0.16 mm |
Bruker P4 diffractometer | 2859 independent reflections |
Radiation source: fine-focus sealed tube | 2586 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.030 |
ω scans | θmax = 25.0°, θmin = 2.1° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −10→10 |
Tmin = 0.653, Tmax = 0.728 | k = −14→11 |
9624 measured reflections | l = −18→17 |
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)] = 0.022 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.057 | H-atom parameters constrained |
S = 1.06 | w = 1/[σ2(Fo2) + (0.0335P)2] where P = (Fo2 + 2Fc2)/3 |
2859 reflections | (Δ/σ)max = 0.002 |
201 parameters | Δρmax = 0.43 e Å−3 |
0 restraints | Δρmin = −0.58 e Å−3 |
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 | ||
I1 | 0.676858 (17) | 0.359553 (14) | 1.062889 (10) | 0.02679 (8) | |
S1 | 0.87276 (7) | 0.64199 (4) | 0.72728 (4) | 0.01893 (14) | |
F1 | 0.76836 (19) | 0.36721 (12) | 0.40767 (9) | 0.0331 (4) | |
O1 | 0.9569 (2) | 0.73551 (15) | 1.00677 (12) | 0.0332 (4) | |
O2 | 0.91565 (19) | 0.77778 (13) | 0.86539 (11) | 0.0257 (4) | |
N1 | 0.9082 (2) | 0.71516 (16) | 0.92705 (13) | 0.0212 (4) | |
N2 | 1.1233 (2) | 0.32525 (16) | 0.70949 (12) | 0.0186 (4) | |
C1 | 0.8368 (2) | 0.61038 (18) | 0.90414 (16) | 0.0166 (5) | |
C2 | 0.7985 (2) | 0.55249 (19) | 0.97514 (15) | 0.0188 (5) | |
H2 | 0.8203 | 0.5797 | 1.0334 | 0.023* | |
C3 | 0.7280 (2) | 0.45449 (19) | 0.95795 (15) | 0.0197 (5) | |
C4 | 0.6940 (2) | 0.41587 (19) | 0.87036 (15) | 0.0201 (5) | |
H4 | 0.6434 | 0.3506 | 0.8585 | 0.024* | |
C5 | 0.7346 (2) | 0.47342 (19) | 0.80063 (15) | 0.0191 (5) | |
H5 | 0.7117 | 0.4456 | 0.7426 | 0.023* | |
C6 | 0.8094 (2) | 0.57271 (18) | 0.81503 (15) | 0.0165 (5) | |
C7 | 0.8391 (2) | 0.54910 (18) | 0.63653 (14) | 0.0160 (5) | |
C8 | 0.9379 (2) | 0.46184 (18) | 0.63142 (14) | 0.0167 (5) | |
C9 | 0.9107 (3) | 0.4005 (2) | 0.55352 (15) | 0.0200 (5) | |
H9 | 0.9730 | 0.3415 | 0.5483 | 0.024* | |
C10 | 0.7897 (3) | 0.4283 (2) | 0.48369 (15) | 0.0221 (5) | |
C11 | 0.6941 (3) | 0.5137 (2) | 0.48648 (15) | 0.0254 (6) | |
H11 | 0.6155 | 0.5309 | 0.4377 | 0.030* | |
C12 | 0.7184 (3) | 0.5738 (2) | 0.56459 (15) | 0.0220 (5) | |
H12 | 0.6533 | 0.6315 | 0.5691 | 0.026* | |
C13 | 1.0778 (2) | 0.43755 (19) | 0.70495 (15) | 0.0185 (5) | |
H13A | 1.1657 | 0.4802 | 0.6950 | 0.022* | |
H13B | 1.0541 | 0.4585 | 0.7625 | 0.022* | |
C14 | 1.0133 (3) | 0.2618 (2) | 0.74903 (16) | 0.0251 (5) | |
H14A | 1.0445 | 0.1882 | 0.7513 | 0.038* | |
H14B | 0.9104 | 0.2687 | 0.7128 | 0.038* | |
H14C | 1.0129 | 0.2868 | 0.8089 | 0.038* | |
C15 | 1.2819 (3) | 0.3150 (2) | 0.76285 (16) | 0.0280 (6) | |
H15A | 1.2852 | 0.3438 | 0.8220 | 0.042* | |
H15B | 1.3536 | 0.3534 | 0.7339 | 0.042* | |
H15C | 1.3109 | 0.2410 | 0.7677 | 0.042* |
U11 | U22 | U33 | U12 | U13 | U23 | |
I1 | 0.03029 (11) | 0.02798 (12) | 0.02461 (12) | −0.00346 (7) | 0.01156 (7) | 0.00507 (7) |
S1 | 0.0243 (3) | 0.0129 (3) | 0.0213 (3) | −0.0010 (2) | 0.0087 (2) | 0.0005 (2) |
F1 | 0.0448 (8) | 0.0394 (10) | 0.0143 (7) | −0.0106 (7) | 0.0040 (7) | −0.0063 (6) |
O1 | 0.0421 (10) | 0.0330 (11) | 0.0253 (9) | −0.0172 (9) | 0.0086 (8) | −0.0137 (8) |
O2 | 0.0311 (9) | 0.0140 (9) | 0.0340 (10) | −0.0047 (7) | 0.0110 (7) | −0.0014 (8) |
N1 | 0.0192 (9) | 0.0182 (11) | 0.0276 (11) | −0.0035 (8) | 0.0081 (8) | −0.0060 (9) |
N2 | 0.0183 (9) | 0.0199 (11) | 0.0183 (10) | 0.0062 (8) | 0.0051 (8) | 0.0030 (9) |
C1 | 0.0157 (10) | 0.0118 (12) | 0.0228 (12) | −0.0017 (9) | 0.0051 (9) | −0.0040 (10) |
C2 | 0.0180 (10) | 0.0227 (13) | 0.0159 (11) | 0.0022 (10) | 0.0040 (9) | −0.0021 (10) |
C3 | 0.0200 (11) | 0.0201 (13) | 0.0211 (12) | 0.0006 (10) | 0.0093 (9) | 0.0035 (10) |
C4 | 0.0205 (11) | 0.0142 (12) | 0.0268 (12) | −0.0034 (9) | 0.0076 (9) | −0.0042 (10) |
C5 | 0.0206 (11) | 0.0176 (12) | 0.0190 (11) | −0.0030 (9) | 0.0035 (9) | −0.0045 (10) |
C6 | 0.0139 (10) | 0.0146 (12) | 0.0217 (11) | 0.0039 (9) | 0.0056 (9) | 0.0013 (10) |
C7 | 0.0183 (10) | 0.0158 (12) | 0.0149 (11) | −0.0013 (9) | 0.0055 (9) | 0.0029 (9) |
C8 | 0.0181 (10) | 0.0173 (12) | 0.0154 (11) | −0.0015 (9) | 0.0053 (9) | 0.0032 (9) |
C9 | 0.0233 (11) | 0.0193 (13) | 0.0189 (12) | 0.0000 (10) | 0.0082 (10) | 0.0011 (10) |
C10 | 0.0263 (12) | 0.0239 (14) | 0.0161 (11) | −0.0112 (11) | 0.0038 (10) | −0.0023 (10) |
C11 | 0.0199 (11) | 0.0358 (16) | 0.0189 (12) | −0.0042 (11) | 0.0002 (9) | 0.0080 (12) |
C12 | 0.0174 (11) | 0.0233 (14) | 0.0260 (13) | 0.0037 (10) | 0.0060 (10) | 0.0067 (11) |
C13 | 0.0185 (11) | 0.0195 (13) | 0.0170 (11) | 0.0024 (10) | 0.0021 (9) | 0.0020 (10) |
C14 | 0.0273 (12) | 0.0243 (14) | 0.0238 (12) | 0.0028 (11) | 0.0053 (10) | 0.0062 (11) |
C15 | 0.0213 (12) | 0.0356 (16) | 0.0272 (13) | 0.0122 (11) | 0.0052 (10) | 0.0047 (12) |
I1—C3 | 2.101 (2) | C7—C12 | 1.393 (3) |
S1—C6 | 1.764 (2) | C7—C8 | 1.404 (3) |
S1—C7 | 1.780 (2) | C8—C9 | 1.388 (3) |
F1—C10 | 1.364 (3) | C8—C13 | 1.513 (3) |
O1—N1 | 1.225 (2) | C9—C10 | 1.384 (3) |
O2—N1 | 1.231 (3) | C9—H9 | 0.9300 |
N1—C1 | 1.465 (3) | C10—C11 | 1.362 (3) |
N2—C13 | 1.460 (3) | C11—C12 | 1.383 (3) |
N2—C14 | 1.461 (3) | C11—H11 | 0.9300 |
N2—C15 | 1.464 (3) | C12—H12 | 0.9300 |
C1—C2 | 1.390 (3) | C13—H13A | 0.9700 |
C1—C6 | 1.404 (3) | C13—H13B | 0.9700 |
C2—C3 | 1.375 (3) | C14—H14A | 0.9600 |
C2—H2 | 0.9300 | C14—H14B | 0.9600 |
C3—C4 | 1.388 (3) | C14—H14C | 0.9600 |
C4—C5 | 1.380 (3) | C15—H15A | 0.9600 |
C4—H4 | 0.9300 | C15—H15B | 0.9600 |
C5—C6 | 1.402 (3) | C15—H15C | 0.9600 |
C5—H5 | 0.9300 | ||
C6—S1—C7 | 103.33 (11) | C10—C9—C8 | 119.2 (2) |
O1—N1—O2 | 123.7 (2) | C10—C9—H9 | 120.4 |
O1—N1—C1 | 118.0 (2) | C8—C9—H9 | 120.4 |
O2—N1—C1 | 118.35 (19) | C11—C10—F1 | 118.9 (2) |
C13—N2—C14 | 110.45 (18) | C11—C10—C9 | 123.6 (2) |
C13—N2—C15 | 109.24 (19) | F1—C10—C9 | 117.4 (2) |
C14—N2—C15 | 110.56 (18) | C10—C11—C12 | 117.6 (2) |
C2—C1—C6 | 123.0 (2) | C10—C11—H11 | 121.2 |
C2—C1—N1 | 116.1 (2) | C12—C11—H11 | 121.2 |
C6—C1—N1 | 120.9 (2) | C11—C12—C7 | 120.8 (2) |
C3—C2—C1 | 119.1 (2) | C11—C12—H12 | 119.6 |
C3—C2—H2 | 120.5 | C7—C12—H12 | 119.6 |
C1—C2—H2 | 120.5 | N2—C13—C8 | 113.66 (18) |
C2—C3—C4 | 119.7 (2) | N2—C13—H13A | 108.8 |
C2—C3—I1 | 121.06 (17) | C8—C13—H13A | 108.8 |
C4—C3—I1 | 119.18 (17) | N2—C13—H13B | 108.8 |
C5—C4—C3 | 120.6 (2) | C8—C13—H13B | 108.8 |
C5—C4—H4 | 119.7 | H13A—C13—H13B | 107.7 |
C3—C4—H4 | 119.7 | N2—C14—H14A | 109.5 |
C4—C5—C6 | 121.7 (2) | N2—C14—H14B | 109.5 |
C4—C5—H5 | 119.1 | H14A—C14—H14B | 109.5 |
C6—C5—H5 | 119.1 | N2—C14—H14C | 109.5 |
C5—C6—C1 | 115.7 (2) | H14A—C14—H14C | 109.5 |
C5—C6—S1 | 121.64 (17) | H14B—C14—H14C | 109.5 |
C1—C6—S1 | 122.56 (18) | N2—C15—H15A | 109.5 |
C12—C7—C8 | 120.6 (2) | N2—C15—H15B | 109.5 |
C12—C7—S1 | 116.28 (18) | H15A—C15—H15B | 109.5 |
C8—C7—S1 | 122.78 (16) | N2—C15—H15C | 109.5 |
C9—C8—C7 | 118.24 (19) | H15A—C15—H15C | 109.5 |
C9—C8—C13 | 119.5 (2) | H15B—C15—H15C | 109.5 |
C7—C8—C13 | 122.1 (2) | ||
O1—N1—C1—C2 | 14.1 (3) | C6—S1—C7—C12 | 109.83 (18) |
O2—N1—C1—C2 | −165.81 (19) | C6—S1—C7—C8 | −77.3 (2) |
O1—N1—C1—C6 | −166.2 (2) | C12—C7—C8—C9 | −0.8 (3) |
O2—N1—C1—C6 | 13.9 (3) | S1—C7—C8—C9 | −173.43 (17) |
C6—C1—C2—C3 | −1.2 (3) | C12—C7—C8—C13 | 175.1 (2) |
N1—C1—C2—C3 | 178.56 (19) | S1—C7—C8—C13 | 2.5 (3) |
C1—C2—C3—C4 | −1.0 (3) | C7—C8—C9—C10 | 1.0 (3) |
C1—C2—C3—I1 | 177.00 (16) | C13—C8—C9—C10 | −175.0 (2) |
C2—C3—C4—C5 | 2.0 (3) | C8—C9—C10—C11 | 0.2 (4) |
I1—C3—C4—C5 | −176.10 (17) | C8—C9—C10—F1 | 178.9 (2) |
C3—C4—C5—C6 | −0.7 (3) | F1—C10—C11—C12 | 179.8 (2) |
C4—C5—C6—C1 | −1.4 (3) | C9—C10—C11—C12 | −1.5 (4) |
C4—C5—C6—S1 | 175.75 (17) | C10—C11—C12—C7 | 1.7 (3) |
C2—C1—C6—C5 | 2.3 (3) | C8—C7—C12—C11 | −0.5 (3) |
N1—C1—C6—C5 | −177.40 (19) | S1—C7—C12—C11 | 172.55 (18) |
C2—C1—C6—S1 | −174.74 (17) | C14—N2—C13—C8 | −74.5 (2) |
N1—C1—C6—S1 | 5.5 (3) | C15—N2—C13—C8 | 163.68 (19) |
C7—S1—C6—C5 | −6.8 (2) | C9—C8—C13—N2 | −29.8 (3) |
C7—S1—C6—C1 | 170.08 (18) | C7—C8—C13—N2 | 154.3 (2) |