Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807018090/ci2349sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807018090/ci2349Isup2.hkl |
CCDC reference: 647168
Key indicators
- Single-crystal X-ray study
- T = 296 K
- Mean (C-C) = 0.012 Å
- R factor = 0.073
- wR factor = 0.231
- Data-to-parameter ratio = 18.5
checkCIF/PLATON results
No syntax errors found
Alert level C PLAT026_ALERT_3_C Ratio Observed / Unique Reflections too Low .... 44 Perc. PLAT030_ALERT_1_C _diffrn_reflns_number .LE. _reflns_number_total ? PLAT062_ALERT_4_C Rescale T(min) & T(max) by ..................... 0.89 PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for C16 PLAT341_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 12
Alert level G ABSTM02_ALERT_3_G When printed, the submitted absorption T values will be replaced by the scaled T values. Since the ratio of scaled T's is identical to the ratio of reported T values, the scaling does not imply a change to the absorption corrections used in the study. Ratio of Tmax expected/reported 0.887 Tmax scaled 0.434 Tmin scaled 0.299
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 5 ALERT level C = Check and explain 1 ALERT level G = General alerts; check 1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 1 ALERT type 2 Indicator that the structure model may be wrong or deficient 3 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: MSC/AFC Diffractometer Control Software (Molecular Structure Corporation, 1994); cell refinement: MSC/AFC Diffractometer Control Software; data reduction: CrystalStructure (Rigaku/MSC, 2005); program(s) used to solve structure: SIR92 (Altomare et al., 1994); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: CrystalStructure.
C16H19BrN2O | Z = 2 |
Mr = 335.24 | F(000) = 344 |
Triclinic, P1 | Dx = 1.508 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71069 Å |
a = 6.9348 (9) Å | Cell parameters from 25 reflections |
b = 10.7030 (19) Å | θ = 12.9–18.5° |
c = 10.882 (3) Å | µ = 2.78 mm−1 |
α = 108.384 (17)° | T = 296 K |
β = 97.601 (16)° | Prism, colorless |
γ = 100.395 (13)° | 0.50 × 0.40 × 0.30 mm |
V = 738.3 (3) Å3 |
Rigaku AFC-6S diffractometer | 1471 reflections with I > 2σ(I) |
Radiation source: normal-focus sealed tube | Rint = 0.000 |
Graphite monochromator | θmax = 27.5°, θmin = 2.0° |
ω/2θ scans | h = −8→8 |
Absorption correction: ψ scan (North et al., 1968) | k = 0→13 |
Tmin = 0.337, Tmax = 0.489 | l = −14→13 |
3376 measured reflections | 3 standard reflections every 150 reflections |
3376 independent reflections | intensity decay: −1.4% |
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)] = 0.073 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.231 | All H-atom parameters refined |
S = 1.00 | w = 1/[σ2(Fo2) + (0.13P)2] where P = (Fo2 + 2Fc2)/3 |
3376 reflections | (Δ/σ)max = 0.001 |
182 parameters | Δρmax = 0.75 e Å−3 |
0 restraints | Δρmin = −1.97 e Å−3 |
Experimental. K; 1H-NMR (CDCl3) δ 7.80–7.83 (dt, 1H, J = 1.1, 7.0 Hz), 7.13–7.28 (m, 4H), 3.70 (s, 3H), 3.63–3.67 (t, 4H, J = 11.9 Hz), 1.57–1.74 (m, 8H); 13C-NMR (CDCl3) δ 166.0, 136.3, 125.6, 122.5, 120.8, 119.0, 113.0, 112.9, 109.5, 49.4, 45.9, 31.4, 29.5, 27.9, 27.4, 26.4; IR ν(film)3053, 2933, 1618, 1535, 1465, 1424, 1265 cm-1; UV λmax (95% EtOH) 204, 222, 284, 292, 364 nm; GCMS m/z 334 (M+), 255, 236 (100%), 130, 103, 77. Anal. Calcd for C16H19BrN2O: C, 57.32; H, 5.71; N, 8.36; Br, 23.83. Found: C, 57.57; H, 5.69; N, 8.35; Br, 23.54. |
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 | ||
Br1 | 0.23455 (13) | 0.15471 (9) | 0.51437 (8) | 0.0537 (4) | |
O1 | 0.4744 (7) | 0.3566 (6) | 0.8708 (5) | 0.0478 (14) | |
N1 | 0.2500 (8) | 0.4173 (7) | 0.5045 (5) | 0.0376 (15) | |
N2 | 0.1542 (8) | 0.3544 (5) | 0.8885 (5) | 0.0275 (12) | |
C2 | 0.2574 (10) | 0.3407 (7) | 0.5834 (6) | 0.0330 (16) | |
C3 | 0.2807 (9) | 0.4183 (7) | 0.7136 (6) | 0.0307 (15) | |
C4 | 0.2914 (9) | 0.5543 (7) | 0.7176 (6) | 0.0276 (14) | |
C5 | 0.3193 (10) | 0.6775 (8) | 0.8191 (8) | 0.0374 (17) | |
H1 | 0.3319 | 0.6823 | 0.9067 | 0.045* | |
C6 | 0.3277 (12) | 0.7931 (8) | 0.7863 (9) | 0.050 (2) | |
H2 | 0.3507 | 0.8767 | 0.8533 | 0.060* | |
C7 | 0.3027 (12) | 0.7869 (9) | 0.6553 (10) | 0.053 (2) | |
H3 | 0.3052 | 0.8662 | 0.6367 | 0.064* | |
C8 | 0.2744 (11) | 0.6662 (9) | 0.5527 (9) | 0.049 (2) | |
H4 | 0.2597 | 0.6626 | 0.4654 | 0.058* | |
C9 | 0.2686 (9) | 0.5496 (7) | 0.5852 (7) | 0.0325 (16) | |
C10 | 0.2196 (11) | 0.3679 (9) | 0.3591 (7) | 0.049 (2) | |
H5 | 0.3470 | 0.3699 | 0.3333 | 0.059* | |
H6 | 0.1528 | 0.4251 | 0.3253 | 0.059* | |
H7 | 0.1392 | 0.2767 | 0.3238 | 0.059* | |
C11 | 0.3103 (10) | 0.3730 (7) | 0.8292 (6) | 0.0269 (14) | |
C12 | −0.0533 (9) | 0.3526 (7) | 0.8330 (7) | 0.0348 (16) | |
H8 | −0.0499 | 0.4079 | 0.7774 | 0.042* | |
H9 | −0.1177 | 0.3922 | 0.9047 | 0.042* | |
C13 | −0.1762 (11) | 0.2097 (8) | 0.7517 (8) | 0.047 (2) | |
H10 | −0.3137 | 0.2140 | 0.7266 | 0.057* | |
H11 | −0.1262 | 0.1780 | 0.6710 | 0.057* | |
C14 | −0.1755 (13) | 0.1055 (8) | 0.8199 (8) | 0.056 (2) | |
H12 | −0.2764 | 0.0237 | 0.7672 | 0.067* | |
H13 | −0.2115 | 0.1406 | 0.9052 | 0.067* | |
C15 | 0.0296 (13) | 0.0693 (8) | 0.8403 (8) | 0.053 (2) | |
H14 | 0.0072 | −0.0228 | 0.8403 | 0.063* | |
H15 | 0.0908 | 0.0716 | 0.7656 | 0.063* | |
C16 | 0.1772 (16) | 0.1622 (9) | 0.9675 (9) | 0.064 (3) | |
H16 | 0.1438 | 0.1338 | 1.0399 | 0.077* | |
H17 | 0.3105 | 0.1500 | 0.9585 | 0.077* | |
C17 | 0.1816 (12) | 0.3106 (8) | 1.0032 (7) | 0.0406 (18) | |
H18 | 0.0768 | 0.3304 | 1.0520 | 0.049* | |
H19 | 0.3088 | 0.3628 | 1.0611 | 0.049* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Br1 | 0.0546 (6) | 0.0505 (5) | 0.0450 (5) | 0.0070 (4) | 0.0179 (4) | 0.0017 (3) |
O1 | 0.028 (3) | 0.080 (4) | 0.046 (3) | 0.025 (3) | 0.006 (2) | 0.031 (3) |
N1 | 0.025 (3) | 0.066 (4) | 0.024 (3) | 0.008 (3) | 0.006 (2) | 0.020 (3) |
N2 | 0.021 (3) | 0.038 (3) | 0.022 (3) | 0.005 (2) | 0.004 (2) | 0.010 (2) |
C2 | 0.027 (4) | 0.044 (4) | 0.023 (3) | 0.003 (3) | 0.002 (3) | 0.009 (3) |
C3 | 0.019 (3) | 0.040 (4) | 0.030 (3) | 0.007 (3) | 0.009 (3) | 0.008 (3) |
C4 | 0.014 (3) | 0.043 (4) | 0.029 (3) | 0.006 (3) | 0.006 (3) | 0.017 (3) |
C5 | 0.019 (4) | 0.050 (4) | 0.045 (4) | 0.009 (3) | 0.003 (3) | 0.020 (3) |
C6 | 0.036 (5) | 0.043 (5) | 0.068 (6) | 0.012 (4) | −0.001 (4) | 0.019 (4) |
C7 | 0.038 (5) | 0.061 (6) | 0.076 (6) | 0.015 (4) | 0.011 (4) | 0.044 (5) |
C8 | 0.022 (4) | 0.078 (6) | 0.059 (5) | 0.010 (4) | 0.004 (3) | 0.044 (5) |
C9 | 0.015 (3) | 0.048 (4) | 0.036 (4) | 0.006 (3) | 0.005 (3) | 0.016 (3) |
C10 | 0.027 (4) | 0.088 (6) | 0.025 (4) | 0.007 (4) | 0.000 (3) | 0.017 (4) |
C11 | 0.031 (4) | 0.037 (4) | 0.015 (3) | 0.013 (3) | 0.007 (3) | 0.009 (3) |
C12 | 0.016 (3) | 0.055 (4) | 0.033 (4) | 0.009 (3) | 0.007 (3) | 0.014 (3) |
C13 | 0.021 (4) | 0.064 (5) | 0.046 (4) | 0.008 (4) | 0.011 (3) | 0.005 (4) |
C14 | 0.051 (5) | 0.048 (5) | 0.045 (5) | −0.012 (4) | 0.021 (4) | −0.008 (4) |
C15 | 0.061 (6) | 0.041 (4) | 0.051 (5) | 0.002 (4) | 0.015 (4) | 0.014 (4) |
C16 | 0.078 (7) | 0.061 (6) | 0.054 (5) | 0.001 (5) | −0.002 (5) | 0.036 (5) |
C17 | 0.044 (4) | 0.049 (4) | 0.027 (4) | 0.004 (4) | 0.006 (3) | 0.016 (3) |
Br1—C2 | 1.861 (7) | C10—H5 | 0.96 |
O1—C11 | 1.232 (8) | C10—H6 | 0.96 |
N1—C2 | 1.363 (9) | C10—H7 | 0.96 |
N1—C9 | 1.383 (9) | C12—C13 | 1.525 (10) |
N1—C10 | 1.474 (8) | C12—H8 | 0.97 |
N2—C11 | 1.348 (8) | C12—H9 | 0.97 |
N2—C17 | 1.467 (9) | C13—C14 | 1.522 (12) |
N2—C12 | 1.479 (8) | C13—H10 | 0.97 |
C2—C3 | 1.368 (9) | C13—H11 | 0.97 |
C3—C4 | 1.431 (10) | C14—C15 | 1.547 (12) |
C3—C11 | 1.487 (9) | C14—H12 | 0.97 |
C4—C5 | 1.389 (10) | C14—H13 | 0.97 |
C4—C9 | 1.413 (9) | C15—C16 | 1.530 (12) |
C5—C6 | 1.385 (11) | C15—H14 | 0.97 |
C5—H1 | 0.93 | C15—H15 | 0.97 |
C6—C7 | 1.392 (12) | C16—C17 | 1.506 (12) |
C6—H2 | 0.93 | C16—H16 | 0.97 |
C7—C8 | 1.376 (12) | C16—H17 | 0.97 |
C7—H3 | 0.93 | C17—H18 | 0.97 |
C8—C9 | 1.396 (11) | C17—H19 | 0.97 |
C8—H4 | 0.93 | ||
C2—N1—C9 | 107.6 (5) | N2—C11—C3 | 117.9 (6) |
C2—N1—C10 | 126.5 (7) | N2—C12—C13 | 112.3 (6) |
C9—N1—C10 | 125.9 (6) | N2—C12—H8 | 109.1 |
C11—N2—C17 | 118.6 (6) | C13—C12—H8 | 109.1 |
C11—N2—C12 | 124.1 (5) | N2—C12—H9 | 109.1 |
C17—N2—C12 | 116.5 (5) | C13—C12—H9 | 109.1 |
N1—C2—C3 | 111.2 (6) | H8—C12—H9 | 107.9 |
N1—C2—Br1 | 121.9 (5) | C14—C13—C12 | 115.7 (6) |
C3—C2—Br1 | 126.9 (6) | C14—C13—H10 | 108.4 |
C2—C3—C4 | 106.4 (6) | C12—C13—H10 | 108.4 |
C2—C3—C11 | 126.8 (6) | C14—C13—H11 | 108.4 |
C4—C3—C11 | 126.5 (6) | C12—C13—H11 | 108.4 |
C5—C4—C9 | 119.7 (6) | H10—C13—H11 | 107.4 |
C5—C4—C3 | 133.9 (6) | C13—C14—C15 | 113.0 (6) |
C9—C4—C3 | 106.4 (6) | C13—C14—H12 | 109.0 |
C6—C5—C4 | 118.2 (7) | C15—C14—H12 | 109.0 |
C6—C5—H1 | 120.9 | C13—C14—H13 | 109.0 |
C4—C5—H1 | 120.9 | C15—C14—H13 | 109.0 |
C5—C6—C7 | 121.5 (8) | H12—C14—H13 | 107.8 |
C5—C6—H2 | 119.2 | C16—C15—C14 | 115.1 (7) |
C7—C6—H2 | 119.2 | C16—C15—H14 | 108.5 |
C8—C7—C6 | 121.5 (8) | C14—C15—H14 | 108.5 |
C8—C7—H3 | 119.2 | C16—C15—H15 | 108.5 |
C6—C7—H3 | 119.2 | C14—C15—H15 | 108.5 |
C7—C8—C9 | 117.3 (7) | H14—C15—H15 | 107.5 |
C7—C8—H4 | 121.4 | C17—C16—C15 | 115.1 (7) |
C9—C8—H4 | 121.4 | C17—C16—H16 | 108.5 |
N1—C9—C8 | 129.9 (7) | C15—C16—H16 | 108.5 |
N1—C9—C4 | 108.4 (6) | C17—C16—H17 | 108.5 |
C8—C9—C4 | 121.7 (7) | C15—C16—H17 | 108.5 |
N1—C10—H5 | 109.5 | H16—C16—H17 | 107.5 |
N1—C10—H6 | 109.5 | N2—C17—C16 | 113.7 (6) |
H5—C10—H6 | 109.5 | N2—C17—H18 | 108.8 |
N1—C10—H7 | 109.5 | C16—C17—H18 | 108.8 |
H5—C10—H7 | 109.5 | N2—C17—H19 | 108.8 |
H6—C10—H7 | 109.5 | C16—C17—H19 | 108.8 |
O1—C11—N2 | 121.4 (6) | H18—C17—H19 | 107.7 |
O1—C11—C3 | 120.6 (6) |