In the crystal structure of the title compound, C
17H
28NO
+·Br
−, the
N-protonated piperidine ring adopts the normal chair conformation. Each bromide anion acts as an acceptor in N—H
Br and O—H
Br hydrogen bonds, resulting in an
R21(8) ring pattern.
Supporting information
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.
2-
tert-Butyl-4-methyl-6-(1-piperidiniomethyl)phenol bromide
top
Crystal data top
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 |
Data collection top
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 top
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 | |
Special details top
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 |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | 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* | |
Atomic displacement parameters (Å2) top | 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) |
Geometric parameters (Å, º) top
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) |
Hydrogen-bond geometry (Å, º) top
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. |