Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805025717/bt6712sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536805025717/bt6712Isup2.hkl |
CCDC reference: 283758
Key indicators
- Single-crystal X-ray study
- T = 263 K
- Mean (C-C) = 0.003 Å
- R factor = 0.026
- wR factor = 0.069
- Data-to-parameter ratio = 21.9
checkCIF/PLATON results
No syntax errors found
Alert level C PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low ....... 0.98 PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ?
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 2 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 1 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 1 ALERT type 3 Indicator that the structure quality may be low 0 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: X-AREA (Stoe & Cie, 2002); cell refinement: X-AREA; data reduction: X-AREA; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: DIAMOND (Brandenburg, 1996); software used to prepare material for publication: SHELXL97.
C16H31N2+·Br−·H2O | Z = 2 |
Mr = 349.34 | F(000) = 372 |
Triclinic, P1 | Dx = 1.221 Mg m−3 |
Hall symbol: -P 1 | Melting point: unknown K |
a = 5.500 (5) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 7.794 (5) Å | Cell parameters from 4273 reflections |
c = 22.961 (5) Å | θ = 2.8–28.3° |
α = 81.893 (5)° | µ = 2.16 mm−1 |
β = 83.761 (5)° | T = 263 K |
γ = 78.102 (5)° | Needle, white |
V = 950.3 (11) Å3 | 0.3 × 0.2 × 0.1 mm |
Stoe IPDS-I diffractometer | 4167 independent reflections |
Radiation source: fine-focus sealed tube | 3523 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.034 |
φ scans | θmax = 27.3°, θmin = 1.8° |
Absorption correction: numerical [X-RED32 (Stoe & Cie, 2002) and X-SHAPE (Stoe & Cie, 2001)] | h = −6→7 |
Tmin = 0.585, Tmax = 0.794 | k = −9→9 |
14912 measured reflections | l = −29→29 |
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)] = 0.026 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.069 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.04 | w = 1/[σ2(Fo2) + (0.0397P)2 + 0.1463P] where P = (Fo2 + 2Fc2)/3 |
4167 reflections | (Δ/σ)max = 0.001 |
190 parameters | Δρmax = 0.24 e Å−3 |
2 restraints | Δρmin = −0.29 e Å−3 |
Experimental. A suitable single-crystal was carefully selected under a polarizing microscope and mounted in a glass capillary. The scattering intensities were collected with an imaging plate diffractometer (Stoe IPDS-I) equipped with a fine focus sealed tube X-ray source (Mo Kα, λ = 0.71073 Å) operating at 50 kV and 30 mA. Intensity data were collected at 263 K by φ scans in 360 frames (0 < φ < 180° exposure time of 10 min) in the 2Θ range 1.91 - 54.78 °·Structure solution and refinement were carried out using the program SHELXL97 (Sheldrick, 1997). A numerical absorption correction (X-RED (Stoe & Cie, 2001) was applied after optimization of the crystal shape (X-SHAPE (Stoe & Cie, 2001)). The final difference maps were free of any chemically significant features. The refinement was based on F2 for ALL reflections. |
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. Carbon-bound H atoms were positioned with idealized geometry (methine d(C—H) = 93 pm, methylene: d(C—H) = 99 pm; methyl: d(C—H) = 98 pm) and refined with fixed isotropic displacement parameters [Uiso(H)=1.5Ueq (for methyl C) and Uiso(H)=1.2Ueq (for methylene C)] using a riding atom model. The methyl groups were idealized, then refined as a rigid group allowed to rotate but not tip. The water H atoms were located in a difference map and their bond length restrained. |
x | y | z | Uiso*/Ueq | Occ. (<1) | |
Br | 0.73175 (3) | 0.32730 (3) | 0.383956 (8) | 0.05446 (8) | |
N1 | 0.4615 (3) | −0.05054 (19) | 0.36555 (6) | 0.0442 (3) | |
N2 | 0.6005 (3) | −0.21059 (19) | 0.44379 (6) | 0.0463 (3) | |
O | 0.1671 (4) | 0.5835 (3) | 0.34933 (13) | 0.1026 (7) | |
H1O | 0.315 (4) | 0.528 (4) | 0.3517 (16) | 0.128 (13)* | |
H2O | 0.084 (5) | 0.500 (3) | 0.3521 (15) | 0.110 (11)* | |
C1 | 0.6543 (3) | −0.1654 (2) | 0.38675 (8) | 0.0472 (4) | |
H1 | 0.8025 | −0.2072 | 0.3652 | 0.057* | |
C2 | 0.3659 (3) | −0.1219 (2) | 0.45970 (8) | 0.0506 (4) | |
H2 | 0.2822 | −0.1296 | 0.4971 | 0.061* | |
C3 | 0.2797 (3) | −0.0214 (3) | 0.41077 (8) | 0.0505 (4) | |
H3 | 0.1252 | 0.0538 | 0.4082 | 0.061* | |
C4 | 0.4544 (4) | 0.0394 (3) | 0.30472 (8) | 0.0525 (4) | |
H4A | 0.6050 | −0.0089 | 0.2817 | 0.063* | |
H4B | 0.4522 | 0.1639 | 0.3053 | 0.063* | |
C5 | 0.2312 (3) | 0.0207 (2) | 0.27513 (7) | 0.0469 (4) | |
H5A | 0.0796 | 0.0754 | 0.2965 | 0.056* | |
H5B | 0.2278 | −0.1035 | 0.2758 | 0.056* | |
C6 | 0.2431 (4) | 0.1079 (3) | 0.21164 (8) | 0.0505 (4) | |
H6A | 0.2505 | 0.2312 | 0.2116 | 0.061* | |
H6B | 0.3959 | 0.0524 | 0.1909 | 0.061* | |
C7 | 0.0246 (3) | 0.0978 (3) | 0.17806 (7) | 0.0498 (4) | |
H7A | −0.1281 | 0.1563 | 0.1980 | 0.060* | |
H7B | 0.0143 | −0.0253 | 0.1788 | 0.060* | |
C8 | 0.0437 (3) | 0.1816 (3) | 0.11422 (8) | 0.0502 (4) | |
H8A | 0.0524 | 0.3049 | 0.1137 | 0.060* | |
H8B | 0.1981 | 0.1242 | 0.0946 | 0.060* | |
C9 | −0.1699 (4) | 0.1712 (3) | 0.07940 (8) | 0.0502 (4) | |
H9A | −0.3246 | 0.2284 | 0.0990 | 0.060* | |
H9B | −0.1783 | 0.0480 | 0.0796 | 0.060* | |
C10 | −0.1486 (3) | 0.2563 (3) | 0.01589 (8) | 0.0503 (4) | |
H10A | 0.0062 | 0.1991 | −0.0036 | 0.060* | |
H10B | −0.1401 | 0.3794 | 0.0157 | 0.060* | |
C11 | −0.3622 (4) | 0.2466 (3) | −0.01946 (8) | 0.0507 (4) | |
H11A | −0.5172 | 0.3038 | 0.0000 | 0.061* | |
H11B | −0.3708 | 0.1235 | −0.0194 | 0.061* | |
C12 | −0.3394 (4) | 0.3321 (3) | −0.08305 (8) | 0.0506 (4) | |
H12A | −0.3312 | 0.4552 | −0.0831 | 0.061* | |
H12B | −0.1840 | 0.2751 | −0.1023 | 0.061* | |
C13 | −0.5513 (4) | 0.3224 (3) | −0.11872 (8) | 0.0513 (4) | |
H13A | −0.5584 | 0.1992 | −0.1190 | 0.062* | |
H13B | −0.7069 | 0.3782 | −0.0991 | 0.062* | |
C14 | −0.5312 (4) | 0.4089 (3) | −0.18186 (8) | 0.0579 (5) | |
H14A | −0.5254 | 0.5323 | −0.1817 | 0.070* | |
H14B | −0.3755 | 0.3535 | −0.2015 | 0.070* | |
C15 | −0.7430 (5) | 0.3974 (3) | −0.21700 (10) | 0.0725 (6) | |
H15A | −0.7183 | 0.4551 | −0.2564 | 0.109* | |
H15B | −0.8978 | 0.4543 | −0.1985 | 0.109* | |
H15C | −0.7473 | 0.2756 | −0.2185 | 0.109* | |
C16 | 0.7654 (4) | −0.3362 (3) | 0.48298 (9) | 0.0606 (5) | |
H16A | 0.6680 | −0.3808 | 0.5168 | 0.091* | 0.50 |
H16B | 0.8842 | −0.2775 | 0.4956 | 0.091* | 0.50 |
H16C | 0.8518 | −0.4325 | 0.4622 | 0.091* | 0.50 |
H16D | 0.9347 | −0.3464 | 0.4662 | 0.091* | 0.50 |
H16E | 0.7184 | −0.4496 | 0.4875 | 0.091* | 0.50 |
H16F | 0.7509 | −0.2947 | 0.5209 | 0.091* | 0.50 |
U11 | U22 | U33 | U12 | U13 | U23 | |
Br | 0.05039 (11) | 0.05782 (12) | 0.05377 (11) | −0.00501 (8) | −0.01003 (8) | −0.00571 (8) |
N1 | 0.0451 (7) | 0.0469 (7) | 0.0403 (7) | −0.0070 (6) | −0.0101 (6) | −0.0025 (6) |
N2 | 0.0477 (8) | 0.0453 (7) | 0.0441 (7) | −0.0008 (6) | −0.0135 (6) | −0.0043 (6) |
O | 0.0575 (10) | 0.0631 (11) | 0.175 (2) | −0.0021 (9) | 0.0001 (12) | 0.0037 (12) |
C1 | 0.0429 (8) | 0.0494 (9) | 0.0477 (9) | −0.0024 (7) | −0.0071 (7) | −0.0084 (7) |
C2 | 0.0489 (9) | 0.0588 (10) | 0.0413 (9) | −0.0022 (8) | −0.0060 (7) | −0.0069 (8) |
C3 | 0.0438 (9) | 0.0561 (10) | 0.0476 (9) | 0.0023 (8) | −0.0089 (7) | −0.0065 (8) |
C4 | 0.0568 (11) | 0.0591 (11) | 0.0434 (9) | −0.0174 (9) | −0.0123 (8) | 0.0027 (8) |
C5 | 0.0492 (9) | 0.0526 (9) | 0.0396 (8) | −0.0115 (8) | −0.0081 (7) | −0.0026 (7) |
C6 | 0.0525 (10) | 0.0569 (10) | 0.0432 (9) | −0.0158 (8) | −0.0099 (8) | 0.0021 (8) |
C7 | 0.0517 (10) | 0.0584 (10) | 0.0406 (9) | −0.0176 (8) | −0.0089 (7) | 0.0036 (7) |
C8 | 0.0508 (10) | 0.0597 (10) | 0.0412 (9) | −0.0165 (8) | −0.0083 (7) | 0.0024 (7) |
C9 | 0.0521 (10) | 0.0577 (10) | 0.0420 (9) | −0.0164 (8) | −0.0094 (8) | 0.0020 (8) |
C10 | 0.0511 (10) | 0.0584 (10) | 0.0428 (9) | −0.0160 (8) | −0.0084 (8) | 0.0009 (8) |
C11 | 0.0537 (10) | 0.0579 (10) | 0.0421 (9) | −0.0168 (8) | −0.0092 (8) | 0.0008 (8) |
C12 | 0.0527 (10) | 0.0574 (10) | 0.0432 (9) | −0.0165 (8) | −0.0088 (8) | 0.0006 (8) |
C13 | 0.0548 (10) | 0.0564 (10) | 0.0439 (9) | −0.0148 (8) | −0.0094 (8) | −0.0002 (8) |
C14 | 0.0631 (12) | 0.0675 (12) | 0.0443 (9) | −0.0183 (10) | −0.0104 (9) | 0.0023 (8) |
C15 | 0.0807 (15) | 0.0894 (16) | 0.0504 (11) | −0.0223 (13) | −0.0224 (11) | 0.0028 (11) |
C16 | 0.0626 (12) | 0.0563 (11) | 0.0569 (11) | 0.0072 (9) | −0.0230 (9) | −0.0005 (9) |
N1—C1 | 1.327 (2) | C9—C10 | 1.517 (2) |
N1—C3 | 1.370 (2) | C9—H9A | 0.9700 |
N1—C4 | 1.472 (2) | C9—H9B | 0.9700 |
N2—C1 | 1.325 (2) | C10—C11 | 1.518 (3) |
N2—C2 | 1.370 (2) | C10—H10A | 0.9700 |
N2—C16 | 1.467 (2) | C10—H10B | 0.9700 |
O—H1O | 0.842 (18) | C11—C12 | 1.521 (2) |
O—H2O | 0.859 (18) | C11—H11A | 0.9700 |
C1—H1 | 0.9300 | C11—H11B | 0.9700 |
C2—C3 | 1.347 (2) | C12—C13 | 1.515 (3) |
C2—H2 | 0.9300 | C12—H12A | 0.9700 |
C3—H3 | 0.9300 | C12—H12B | 0.9700 |
C4—C5 | 1.508 (3) | C13—C14 | 1.513 (2) |
C4—H4A | 0.9700 | C13—H13A | 0.9700 |
C4—H4B | 0.9700 | C13—H13B | 0.9700 |
C5—C6 | 1.520 (2) | C14—C15 | 1.511 (3) |
C5—H5A | 0.9700 | C14—H14A | 0.9700 |
C5—H5B | 0.9700 | C14—H14B | 0.9700 |
C6—C7 | 1.517 (3) | C15—H15A | 0.9600 |
C6—H6A | 0.9700 | C15—H15B | 0.9600 |
C6—H6B | 0.9700 | C15—H15C | 0.9600 |
C7—C8 | 1.520 (2) | C16—H16A | 0.9600 |
C7—H7A | 0.9700 | C16—H16B | 0.9600 |
C7—H7B | 0.9700 | C16—H16C | 0.9600 |
C8—C9 | 1.513 (3) | C16—H16D | 0.9600 |
C8—H8A | 0.9700 | C16—H16E | 0.9600 |
C8—H8B | 0.9700 | C16—H16F | 0.9600 |
C1—N1—C3 | 108.37 (15) | C9—C10—H10B | 108.7 |
C1—N1—C4 | 125.22 (15) | C11—C10—H10B | 108.7 |
C3—N1—C4 | 126.26 (15) | H10A—C10—H10B | 107.6 |
C1—N2—C2 | 108.71 (14) | C10—C11—C12 | 114.00 (16) |
C1—N2—C16 | 125.31 (16) | C10—C11—H11A | 108.8 |
C2—N2—C16 | 125.98 (16) | C12—C11—H11A | 108.8 |
H1O—O—H2O | 103 (3) | C10—C11—H11B | 108.8 |
N2—C1—N1 | 108.66 (15) | C12—C11—H11B | 108.8 |
N2—C1—H1 | 125.7 | H11A—C11—H11B | 107.6 |
N1—C1—H1 | 125.7 | C13—C12—C11 | 114.36 (16) |
C3—C2—N2 | 106.90 (16) | C13—C12—H12A | 108.7 |
C3—C2—H2 | 126.5 | C11—C12—H12A | 108.7 |
N2—C2—H2 | 126.5 | C13—C12—H12B | 108.7 |
C2—C3—N1 | 107.36 (16) | C11—C12—H12B | 108.7 |
C2—C3—H3 | 126.3 | H12A—C12—H12B | 107.6 |
N1—C3—H3 | 126.3 | C14—C13—C12 | 114.63 (16) |
N1—C4—C5 | 113.05 (15) | C14—C13—H13A | 108.6 |
N1—C4—H4A | 109.0 | C12—C13—H13A | 108.6 |
C5—C4—H4A | 109.0 | C14—C13—H13B | 108.6 |
N1—C4—H4B | 109.0 | C12—C13—H13B | 108.6 |
C5—C4—H4B | 109.0 | H13A—C13—H13B | 107.6 |
H4A—C4—H4B | 107.8 | C15—C14—C13 | 114.08 (18) |
C4—C5—C6 | 110.22 (15) | C15—C14—H14A | 108.7 |
C4—C5—H5A | 109.6 | C13—C14—H14A | 108.7 |
C6—C5—H5A | 109.6 | C15—C14—H14B | 108.7 |
C4—C5—H5B | 109.6 | C13—C14—H14B | 108.7 |
C6—C5—H5B | 109.6 | H14A—C14—H14B | 107.6 |
H5A—C5—H5B | 108.1 | C14—C15—H15A | 109.5 |
C7—C6—C5 | 114.32 (16) | C14—C15—H15B | 109.5 |
C7—C6—H6A | 108.7 | H15A—C15—H15B | 109.5 |
C5—C6—H6A | 108.7 | C14—C15—H15C | 109.5 |
C7—C6—H6B | 108.7 | H15A—C15—H15C | 109.5 |
C5—C6—H6B | 108.7 | H15B—C15—H15C | 109.5 |
H6A—C6—H6B | 107.6 | N2—C16—H16A | 109.5 |
C6—C7—C8 | 113.41 (16) | N2—C16—H16B | 109.5 |
C6—C7—H7A | 108.9 | H16A—C16—H16B | 109.5 |
C8—C7—H7A | 108.9 | N2—C16—H16C | 109.5 |
C6—C7—H7B | 108.9 | H16A—C16—H16C | 109.5 |
C8—C7—H7B | 108.9 | H16B—C16—H16C | 109.5 |
H7A—C7—H7B | 107.7 | N2—C16—H16D | 109.5 |
C9—C8—C7 | 114.58 (16) | H16A—C16—H16D | 141.1 |
C9—C8—H8A | 108.6 | H16B—C16—H16D | 56.3 |
C7—C8—H8A | 108.6 | H16C—C16—H16D | 56.3 |
C9—C8—H8B | 108.6 | N2—C16—H16E | 109.5 |
C7—C8—H8B | 108.6 | H16A—C16—H16E | 56.3 |
H8A—C8—H8B | 107.6 | H16B—C16—H16E | 141.1 |
C8—C9—C10 | 113.90 (16) | H16C—C16—H16E | 56.3 |
C8—C9—H9A | 108.8 | H16D—C16—H16E | 109.5 |
C10—C9—H9A | 108.8 | N2—C16—H16F | 109.5 |
C8—C9—H9B | 108.8 | H16A—C16—H16F | 56.3 |
C10—C9—H9B | 108.8 | H16B—C16—H16F | 56.3 |
H9A—C9—H9B | 107.7 | H16C—C16—H16F | 141.1 |
C9—C10—C11 | 114.33 (16) | H16D—C16—H16F | 109.5 |
C9—C10—H10A | 108.7 | H16E—C16—H16F | 109.5 |
C11—C10—H10A | 108.7 |
D—H···A | D—H | H···A | D···A | D—H···A |
O—H2O···Bri | 0.86 (2) | 2.57 (2) | 3.386 (3) | 159 (3) |
O—H1O···Br | 0.84 (2) | 2.61 (2) | 3.435 (3) | 166 (3) |
C3—H3···Bri | 0.93 | 2.75 | 3.661 (3) | 167 |
C1—H1···Oii | 0.93 | 2.34 | 3.193 (4) | 152 |
Symmetry codes: (i) x−1, y, z; (ii) x+1, y−1, z. |
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