Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536803021299/wn6187sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536803021299/wn6187IIIsup2.hkl |
CCDC reference: 225866
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.014 Å
- R factor = 0.063
- wR factor = 0.122
- Data-to-parameter ratio = 17.3
checkCIF/PLATON results
No syntax errors found
Alert level C PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low ....... 0.99 PLAT094_ALERT_2_C Ratio of Maximum / Minimum Residual Density .... 2.23 PLAT222_ALERT_3_C Large Non-Solvent H Ueq(max)/Ueq(min) ... 3.04 Ratio PLAT341_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 14
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 25.01 From the CIF: _reflns_number_total 3211 Count of symmetry unique reflns 1906 Completeness (_total/calc) 168.47% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 1305 Fraction of Friedel pairs measured 0.685 Are heavy atom types Z>Si present yes
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 4 ALERT level C = Check and explain 1 ALERT level G = General alerts; check 0 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
Data collection: SMART (Bruker, 1998); cell refinement: SMART; data reduction: SAINT (Bruker, 1998); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: XP in SHELXTL (Bruker, 1998); software used to prepare material for publication: SHELXL97.
C17H28NO+·Br− | F(000) = 720 |
Mr = 342.30 | Dx = 1.232 Mg m−3 |
Orthorhombic, P212121 | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: P_2ac_2ab | Cell parameters from 673 reflections |
a = 5.987 (4) Å | θ = 2.3–19.5° |
b = 12.604 (8) Å | µ = 2.22 mm−1 |
c = 24.469 (15) Å | T = 293 K |
V = 1846 (2) Å3 | Cut needle, colorless |
Z = 4 | 0.30 × 0.20 × 0.10 mm |
Bruker SMART 1000 diffractometer | 1809 reflections with I > 2σ(I) |
ω scans | Rint = 0.100 |
Absorption correction: multi-scan (SADABS; Sheldrick, 1997) | θmax = 25.0° |
Tmin = 0.555, Tmax = 0.808 | h = −7→5 |
6633 measured reflections | k = −14→14 |
3211 independent reflections | l = −26→29 |
Refinement on F2 | w = 1/[σ2(Fo2) + (0.034P)2 + 2.308P] where P = (Fo2 + 2Fc2)/3 |
R[F2 > 2σ(F2)] = 0.063 | (Δ/σ)max = 0.001 |
wR(F2) = 0.122 | Δρmax = 0.60 e Å−3 |
S = 1.04 | Δρmin = −0.27 e Å−3 |
3211 reflections | Absolute structure: Flack (1983); 1305 Friedel pairs |
186 parameters | Absolute structure parameter: 0.05 (3) |
H-atom parameters constrained |
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. Full-MATRIX |
x | y | z | Uiso*/Ueq | ||
Br1 | 0.65975 (15) | 0.61668 (7) | 0.25746 (4) | 0.0589 (3) | |
C1 | −0.1765 (16) | 0.9162 (6) | 0.2641 (4) | 0.056 (2) | |
H1A | −0.2670 | 0.8524 | 0.2645 | 0.067* | |
H1B | −0.2614 | 0.9718 | 0.2463 | 0.067* | |
C2 | −0.1217 (19) | 0.9495 (9) | 0.3229 (4) | 0.077 (3) | |
H2A | −0.2592 | 0.9589 | 0.3433 | 0.092* | |
H2B | −0.0430 | 1.0168 | 0.3225 | 0.092* | |
C3 | 0.024 (2) | 0.8648 (12) | 0.3509 (4) | 0.088 (4) | |
H3A | 0.0611 | 0.8877 | 0.3877 | 0.106* | |
H3B | −0.0581 | 0.7987 | 0.3535 | 0.106* | |
C4 | 0.2348 (17) | 0.8481 (9) | 0.3185 (4) | 0.068 (3) | |
H4A | 0.3252 | 0.7942 | 0.3362 | 0.082* | |
H4B | 0.3201 | 0.9135 | 0.3178 | 0.082* | |
C5 | 0.1834 (15) | 0.8140 (6) | 0.2605 (3) | 0.050 (2) | |
H5A | 0.3215 | 0.8060 | 0.2402 | 0.060* | |
H5B | 0.1076 | 0.7460 | 0.2609 | 0.060* | |
C6 | −0.0192 (15) | 0.8619 (8) | 0.1744 (3) | 0.053 (3) | |
H6A | −0.0841 | 0.7914 | 0.1752 | 0.064* | |
H6B | −0.1301 | 0.9099 | 0.1595 | 0.064* | |
C7 | 0.1837 (16) | 0.8609 (7) | 0.1369 (3) | 0.047 (2) | |
C8 | 0.2533 (14) | 0.9549 (8) | 0.1115 (4) | 0.042 (2) | |
C9 | 0.4306 (15) | 0.9530 (7) | 0.0734 (4) | 0.043 (2) | |
C10 | 0.5328 (16) | 0.8546 (8) | 0.0639 (4) | 0.060 (3) | |
H10 | 0.6493 | 0.8514 | 0.0389 | 0.072* | |
C11 | 0.468 (2) | 0.7595 (9) | 0.0907 (4) | 0.066 (3) | |
C12 | 0.2910 (19) | 0.7648 (8) | 0.1250 (4) | 0.063 (3) | |
H12 | 0.2391 | 0.7028 | 0.1412 | 0.076* | |
C13 | 0.600 (2) | 0.6587 (8) | 0.0782 (5) | 0.099 (4) | |
H13A | 0.7566 | 0.6745 | 0.0785 | 0.149* | |
H13B | 0.5577 | 0.6322 | 0.0429 | 0.149* | |
H13C | 0.5678 | 0.6061 | 0.1055 | 0.149* | |
C14 | 0.5066 (15) | 1.0554 (8) | 0.0429 (4) | 0.051 (3) | |
C15 | 0.3083 (16) | 1.1059 (8) | 0.0127 (3) | 0.072 (3) | |
H15A | 0.3607 | 1.1635 | −0.0095 | 0.108* | |
H15B | 0.2023 | 1.1321 | 0.0389 | 0.108* | |
H15C | 0.2379 | 1.0536 | −0.0100 | 0.108* | |
C16 | 0.6029 (17) | 1.1357 (8) | 0.0847 (4) | 0.066 (3) | |
H16A | 0.7317 | 1.1055 | 0.1022 | 0.100* | |
H16B | 0.4917 | 1.1517 | 0.1118 | 0.100* | |
H16C | 0.6451 | 1.1997 | 0.0661 | 0.100* | |
C17 | 0.6906 (18) | 1.0331 (8) | 0.0011 (4) | 0.078 (3) | |
H17A | 0.7269 | 1.0974 | −0.0179 | 0.116* | |
H17B | 0.6395 | 0.9809 | −0.0245 | 0.116* | |
H17C | 0.8209 | 1.0071 | 0.0196 | 0.116* | |
N1 | 0.0368 (10) | 0.8959 (5) | 0.2328 (2) | 0.0408 (17) | |
H1C | 0.1145 | 0.9579 | 0.2311 | 0.049* | |
O1 | 0.1430 (12) | 1.0472 (5) | 0.1248 (2) | 0.0558 (16) | |
H1 | 0.1887 | 1.0693 | 0.1542 | 0.084* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Br1 | 0.0598 (5) | 0.0360 (4) | 0.0808 (6) | 0.0046 (6) | −0.0054 (6) | 0.0022 (6) |
C1 | 0.045 (5) | 0.041 (5) | 0.081 (6) | 0.002 (5) | 0.002 (6) | −0.009 (5) |
C2 | 0.061 (8) | 0.072 (8) | 0.099 (9) | −0.002 (7) | 0.027 (7) | −0.030 (7) |
C3 | 0.102 (10) | 0.097 (11) | 0.066 (8) | −0.005 (10) | 0.017 (7) | −0.011 (8) |
C4 | 0.072 (8) | 0.077 (9) | 0.055 (6) | −0.002 (6) | −0.008 (5) | 0.010 (6) |
C5 | 0.050 (5) | 0.051 (5) | 0.049 (5) | 0.006 (5) | 0.004 (6) | 0.011 (5) |
C6 | 0.048 (6) | 0.050 (7) | 0.062 (6) | −0.023 (6) | −0.008 (5) | 0.014 (5) |
C7 | 0.052 (6) | 0.045 (6) | 0.043 (5) | −0.003 (6) | 0.003 (5) | 0.001 (4) |
C8 | 0.043 (6) | 0.039 (6) | 0.044 (6) | −0.002 (4) | −0.013 (5) | 0.005 (5) |
C9 | 0.048 (6) | 0.040 (6) | 0.040 (6) | −0.011 (5) | −0.006 (5) | −0.004 (5) |
C10 | 0.062 (7) | 0.069 (9) | 0.050 (6) | 0.002 (6) | 0.000 (5) | −0.020 (6) |
C11 | 0.082 (9) | 0.046 (7) | 0.070 (8) | −0.001 (7) | −0.003 (7) | −0.011 (6) |
C12 | 0.082 (9) | 0.048 (7) | 0.061 (7) | −0.021 (6) | 0.003 (6) | −0.005 (5) |
C13 | 0.134 (12) | 0.054 (8) | 0.110 (9) | 0.014 (8) | 0.012 (9) | −0.025 (7) |
C14 | 0.047 (6) | 0.057 (7) | 0.050 (6) | −0.004 (5) | 0.001 (5) | 0.012 (5) |
C15 | 0.075 (7) | 0.081 (8) | 0.060 (5) | −0.024 (8) | −0.020 (6) | 0.028 (6) |
C16 | 0.067 (7) | 0.061 (7) | 0.072 (6) | −0.017 (6) | −0.008 (6) | 0.003 (6) |
C17 | 0.081 (9) | 0.078 (8) | 0.074 (7) | −0.020 (8) | 0.011 (7) | 0.013 (6) |
N1 | 0.039 (4) | 0.034 (4) | 0.048 (4) | −0.004 (3) | −0.001 (3) | 0.005 (4) |
O1 | 0.057 (4) | 0.051 (4) | 0.059 (4) | 0.009 (4) | 0.002 (4) | 0.010 (3) |
C1—N1 | 1.511 (8) | C9—C10 | 1.402 (9) |
C1—C2 | 1.533 (9) | C9—C14 | 1.559 (9) |
C1—H1A | 0.9700 | C10—C11 | 1.420 (8) |
C1—H1B | 0.9700 | C10—H10 | 0.9300 |
C2—C3 | 1.540 (11) | C11—C12 | 1.352 (8) |
C2—H2A | 0.9700 | C11—C13 | 1.526 (9) |
C2—H2B | 0.9700 | C12—H12 | 0.9300 |
C3—C4 | 1.506 (11) | C13—H13A | 0.9600 |
C3—H3A | 0.9700 | C13—H13B | 0.9600 |
C3—H3B | 0.9700 | C13—H13C | 0.9600 |
C4—C5 | 1.516 (12) | C14—C17 | 1.528 (9) |
C4—H4A | 0.9700 | C14—C15 | 1.536 (10) |
C4—H4B | 0.9700 | C14—C16 | 1.552 (8) |
C5—N1 | 1.514 (9) | C15—H15A | 0.9600 |
C5—H5A | 0.9700 | C15—H15B | 0.9600 |
C5—H5B | 0.9700 | C15—H15C | 0.9600 |
C6—C7 | 1.522 (8) | C16—H16A | 0.9600 |
C6—N1 | 1.528 (9) | C16—H16B | 0.9600 |
C6—H6A | 0.9700 | C16—H16C | 0.9600 |
C6—H6B | 0.9700 | C17—H17A | 0.9600 |
C7—C12 | 1.402 (14) | C17—H17B | 0.9600 |
C7—C8 | 1.400 (12) | C17—H17C | 0.9600 |
C8—O1 | 1.377 (10) | N1—H1C | 0.9100 |
C8—C9 | 1.414 (8) | O1—H1 | 0.8200 |
N1—C1—C2 | 110.0 (8) | C9—C10—H10 | 118.3 |
N1—C1—H1A | 109.7 | C11—C10—H10 | 118.3 |
C2—C1—H1A | 109.7 | C12—C11—C10 | 117.3 (10) |
N1—C1—H1B | 109.7 | C12—C11—C13 | 124.8 (11) |
C2—C1—H1B | 109.7 | C10—C11—C13 | 117.9 (11) |
H1A—C1—H1B | 108.2 | C11—C12—C7 | 122.0 (10) |
C1—C2—C3 | 110.5 (9) | C11—C12—H12 | 119.0 |
C1—C2—H2A | 109.6 | C7—C12—H12 | 119.0 |
C3—C2—H2A | 109.6 | C11—C13—H13A | 109.5 |
C1—C2—H2B | 109.6 | C11—C13—H13B | 109.5 |
C3—C2—H2B | 109.6 | H13A—C13—H13B | 109.5 |
H2A—C2—H2B | 108.1 | C11—C13—H13C | 109.5 |
C4—C3—C2 | 109.7 (9) | H13A—C13—H13C | 109.5 |
C4—C3—H3A | 109.7 | H13B—C13—H13C | 109.5 |
C2—C3—H3A | 109.7 | C17—C14—C15 | 108.2 (8) |
C4—C3—H3B | 109.7 | C17—C14—C16 | 107.0 (8) |
C2—C3—H3B | 109.7 | C15—C14—C16 | 109.5 (8) |
H3A—C3—H3B | 108.2 | C17—C14—C9 | 112.2 (8) |
C3—C4—C5 | 111.3 (8) | C15—C14—C9 | 110.3 (7) |
C3—C4—H4A | 109.4 | C16—C14—C9 | 109.4 (7) |
C5—C4—H4A | 109.4 | C14—C15—H15A | 109.5 |
C3—C4—H4B | 109.4 | C14—C15—H15B | 109.5 |
C5—C4—H4B | 109.4 | H15A—C15—H15B | 109.5 |
H4A—C4—H4B | 108.0 | C14—C15—H15C | 109.5 |
N1—C5—C4 | 110.1 (7) | H15A—C15—H15C | 109.5 |
N1—C5—H5A | 109.6 | H15B—C15—H15C | 109.5 |
C4—C5—H5A | 109.6 | C14—C16—H16A | 109.5 |
N1—C5—H5B | 109.6 | C14—C16—H16B | 109.5 |
C4—C5—H5B | 109.6 | H16A—C16—H16B | 109.5 |
H5A—C5—H5B | 108.2 | C14—C16—H16C | 109.5 |
C7—C6—N1 | 113.0 (7) | H16A—C16—H16C | 109.5 |
C7—C6—H6A | 109.0 | H16B—C16—H16C | 109.5 |
N1—C6—H6A | 109.0 | C14—C17—H17A | 109.5 |
C7—C6—H6B | 109.0 | C14—C17—H17B | 109.5 |
N1—C6—H6B | 109.0 | H17A—C17—H17B | 109.5 |
H6A—C6—H6B | 107.8 | C14—C17—H17C | 109.5 |
C12—C7—C8 | 120.2 (9) | H17A—C17—H17C | 109.5 |
C12—C7—C6 | 119.9 (9) | H17B—C17—H17C | 109.5 |
C8—C7—C6 | 119.9 (9) | C1—N1—C5 | 112.2 (6) |
O1—C8—C7 | 117.9 (8) | C1—N1—C6 | 109.6 (6) |
O1—C8—C9 | 122.0 (8) | C5—N1—C6 | 110.7 (7) |
C7—C8—C9 | 120.1 (9) | C1—N1—H1C | 108.0 |
C10—C9—C8 | 116.8 (9) | C5—N1—H1C | 108.0 |
C10—C9—C14 | 121.7 (9) | C6—N1—H1C | 108.0 |
C8—C9—C14 | 121.4 (9) | C8—O1—H1 | 109.5 |
C9—C10—C11 | 123.4 (9) | ||
N1—C1—C2—C3 | −56.3 (10) | C9—C10—C11—C13 | −177.6 (10) |
C1—C2—C3—C4 | 57.8 (13) | C10—C11—C12—C7 | −4.0 (15) |
C2—C3—C4—C5 | −58.5 (13) | C13—C11—C12—C7 | 176.6 (10) |
C3—C4—C5—N1 | 57.5 (12) | C8—C7—C12—C11 | 2.3 (14) |
N1—C6—C7—C12 | 100.2 (10) | C6—C7—C12—C11 | 178.0 (9) |
N1—C6—C7—C8 | −84.1 (10) | C10—C9—C14—C17 | 2.9 (12) |
C12—C7—C8—O1 | −179.8 (8) | C8—C9—C14—C17 | −176.4 (7) |
C6—C7—C8—O1 | 4.6 (12) | C10—C9—C14—C15 | 123.7 (9) |
C12—C7—C8—C9 | 0.6 (13) | C8—C9—C14—C15 | −55.7 (11) |
C6—C7—C8—C9 | −175.0 (7) | C10—C9—C14—C16 | −115.8 (10) |
O1—C8—C9—C10 | 178.9 (8) | C8—C9—C14—C16 | 64.9 (10) |
C7—C8—C9—C10 | −1.6 (12) | C2—C1—N1—C5 | 56.1 (9) |
O1—C8—C9—C14 | −1.7 (12) | C2—C1—N1—C6 | 179.6 (7) |
C7—C8—C9—C14 | 177.8 (8) | C4—C5—N1—C1 | −56.4 (9) |
C8—C9—C10—C11 | −0.3 (13) | C4—C5—N1—C6 | −179.2 (7) |
C14—C9—C10—C11 | −179.7 (9) | C7—C6—N1—C1 | 168.6 (7) |
C9—C10—C11—C12 | 3.1 (15) | C7—C6—N1—C5 | −67.0 (10) |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1C···Br1i | 0.91 | 2.43 | 3.332 (8) | 170 |
O1—H1···Br1i | 0.82 | 2.42 | 3.235 (9) | 174 |
Symmetry code: (i) −x+1, y+1/2, −z+1/2. |
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