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In the crystal structure of the title compound, C17H28NO+·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

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536803021299/wn6187sup1.cif
Contains datablocks global, III

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536803021299/wn6187IIIsup2.hkl
Contains datablock III

CCDC reference: 225866

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](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

Computing details top

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+·BrF(000) = 720
Mr = 342.30Dx = 1.232 Mg m3
Orthorhombic, P212121Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P_2ac_2abCell parameters from 673 reflections
a = 5.987 (4) Åθ = 2.3–19.5°
b = 12.604 (8) ŵ = 2.22 mm1
c = 24.469 (15) ÅT = 293 K
V = 1846 (2) Å3Cut needle, colorless
Z = 40.30 × 0.20 × 0.10 mm
Data collection top
Bruker SMART 1000
diffractometer
1809 reflections with I > 2σ(I)
ω scansRint = 0.100
Absorption correction: multi-scan
(SADABS; Sheldrick, 1997)
θmax = 25.0°
Tmin = 0.555, Tmax = 0.808h = 75
6633 measured reflectionsk = 1414
3211 independent reflectionsl = 2629
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) = 0.122Δρmax = 0.60 e Å3
S = 1.04Δρmin = 0.27 e Å3
3211 reflectionsAbsolute structure: Flack (1983); 1305 Friedel pairs
186 parametersAbsolute 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
xyzUiso*/Ueq
Br10.65975 (15)0.61668 (7)0.25746 (4)0.0589 (3)
C10.1765 (16)0.9162 (6)0.2641 (4)0.056 (2)
H1A0.26700.85240.26450.067*
H1B0.26140.97180.24630.067*
C20.1217 (19)0.9495 (9)0.3229 (4)0.077 (3)
H2A0.25920.95890.34330.092*
H2B0.04301.01680.32250.092*
C30.024 (2)0.8648 (12)0.3509 (4)0.088 (4)
H3A0.06110.88770.38770.106*
H3B0.05810.79870.35350.106*
C40.2348 (17)0.8481 (9)0.3185 (4)0.068 (3)
H4A0.32520.79420.33620.082*
H4B0.32010.91350.31780.082*
C50.1834 (15)0.8140 (6)0.2605 (3)0.050 (2)
H5A0.32150.80600.24020.060*
H5B0.10760.74600.26090.060*
C60.0192 (15)0.8619 (8)0.1744 (3)0.053 (3)
H6A0.08410.79140.17520.064*
H6B0.13010.90990.15950.064*
C70.1837 (16)0.8609 (7)0.1369 (3)0.047 (2)
C80.2533 (14)0.9549 (8)0.1115 (4)0.042 (2)
C90.4306 (15)0.9530 (7)0.0734 (4)0.043 (2)
C100.5328 (16)0.8546 (8)0.0639 (4)0.060 (3)
H100.64930.85140.03890.072*
C110.468 (2)0.7595 (9)0.0907 (4)0.066 (3)
C120.2910 (19)0.7648 (8)0.1250 (4)0.063 (3)
H120.23910.70280.14120.076*
C130.600 (2)0.6587 (8)0.0782 (5)0.099 (4)
H13A0.75660.67450.07850.149*
H13B0.55770.63220.04290.149*
H13C0.56780.60610.10550.149*
C140.5066 (15)1.0554 (8)0.0429 (4)0.051 (3)
C150.3083 (16)1.1059 (8)0.0127 (3)0.072 (3)
H15A0.36071.16350.00950.108*
H15B0.20231.13210.03890.108*
H15C0.23791.05360.01000.108*
C160.6029 (17)1.1357 (8)0.0847 (4)0.066 (3)
H16A0.73171.10550.10220.100*
H16B0.49171.15170.11180.100*
H16C0.64511.19970.06610.100*
C170.6906 (18)1.0331 (8)0.0011 (4)0.078 (3)
H17A0.72691.09740.01790.116*
H17B0.63950.98090.02450.116*
H17C0.82091.00710.01960.116*
N10.0368 (10)0.8959 (5)0.2328 (2)0.0408 (17)
H1C0.11450.95790.23110.049*
O10.1430 (12)1.0472 (5)0.1248 (2)0.0558 (16)
H10.18871.06930.15420.084*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Br10.0598 (5)0.0360 (4)0.0808 (6)0.0046 (6)0.0054 (6)0.0022 (6)
C10.045 (5)0.041 (5)0.081 (6)0.002 (5)0.002 (6)0.009 (5)
C20.061 (8)0.072 (8)0.099 (9)0.002 (7)0.027 (7)0.030 (7)
C30.102 (10)0.097 (11)0.066 (8)0.005 (10)0.017 (7)0.011 (8)
C40.072 (8)0.077 (9)0.055 (6)0.002 (6)0.008 (5)0.010 (6)
C50.050 (5)0.051 (5)0.049 (5)0.006 (5)0.004 (6)0.011 (5)
C60.048 (6)0.050 (7)0.062 (6)0.023 (6)0.008 (5)0.014 (5)
C70.052 (6)0.045 (6)0.043 (5)0.003 (6)0.003 (5)0.001 (4)
C80.043 (6)0.039 (6)0.044 (6)0.002 (4)0.013 (5)0.005 (5)
C90.048 (6)0.040 (6)0.040 (6)0.011 (5)0.006 (5)0.004 (5)
C100.062 (7)0.069 (9)0.050 (6)0.002 (6)0.000 (5)0.020 (6)
C110.082 (9)0.046 (7)0.070 (8)0.001 (7)0.003 (7)0.011 (6)
C120.082 (9)0.048 (7)0.061 (7)0.021 (6)0.003 (6)0.005 (5)
C130.134 (12)0.054 (8)0.110 (9)0.014 (8)0.012 (9)0.025 (7)
C140.047 (6)0.057 (7)0.050 (6)0.004 (5)0.001 (5)0.012 (5)
C150.075 (7)0.081 (8)0.060 (5)0.024 (8)0.020 (6)0.028 (6)
C160.067 (7)0.061 (7)0.072 (6)0.017 (6)0.008 (6)0.003 (6)
C170.081 (9)0.078 (8)0.074 (7)0.020 (8)0.011 (7)0.013 (6)
N10.039 (4)0.034 (4)0.048 (4)0.004 (3)0.001 (3)0.005 (4)
O10.057 (4)0.051 (4)0.059 (4)0.009 (4)0.002 (4)0.010 (3)
Geometric parameters (Å, º) top
C1—N11.511 (8)C9—C101.402 (9)
C1—C21.533 (9)C9—C141.559 (9)
C1—H1A0.9700C10—C111.420 (8)
C1—H1B0.9700C10—H100.9300
C2—C31.540 (11)C11—C121.352 (8)
C2—H2A0.9700C11—C131.526 (9)
C2—H2B0.9700C12—H120.9300
C3—C41.506 (11)C13—H13A0.9600
C3—H3A0.9700C13—H13B0.9600
C3—H3B0.9700C13—H13C0.9600
C4—C51.516 (12)C14—C171.528 (9)
C4—H4A0.9700C14—C151.536 (10)
C4—H4B0.9700C14—C161.552 (8)
C5—N11.514 (9)C15—H15A0.9600
C5—H5A0.9700C15—H15B0.9600
C5—H5B0.9700C15—H15C0.9600
C6—C71.522 (8)C16—H16A0.9600
C6—N11.528 (9)C16—H16B0.9600
C6—H6A0.9700C16—H16C0.9600
C6—H6B0.9700C17—H17A0.9600
C7—C121.402 (14)C17—H17B0.9600
C7—C81.400 (12)C17—H17C0.9600
C8—O11.377 (10)N1—H1C0.9100
C8—C91.414 (8)O1—H10.8200
N1—C1—C2110.0 (8)C9—C10—H10118.3
N1—C1—H1A109.7C11—C10—H10118.3
C2—C1—H1A109.7C12—C11—C10117.3 (10)
N1—C1—H1B109.7C12—C11—C13124.8 (11)
C2—C1—H1B109.7C10—C11—C13117.9 (11)
H1A—C1—H1B108.2C11—C12—C7122.0 (10)
C1—C2—C3110.5 (9)C11—C12—H12119.0
C1—C2—H2A109.6C7—C12—H12119.0
C3—C2—H2A109.6C11—C13—H13A109.5
C1—C2—H2B109.6C11—C13—H13B109.5
C3—C2—H2B109.6H13A—C13—H13B109.5
H2A—C2—H2B108.1C11—C13—H13C109.5
C4—C3—C2109.7 (9)H13A—C13—H13C109.5
C4—C3—H3A109.7H13B—C13—H13C109.5
C2—C3—H3A109.7C17—C14—C15108.2 (8)
C4—C3—H3B109.7C17—C14—C16107.0 (8)
C2—C3—H3B109.7C15—C14—C16109.5 (8)
H3A—C3—H3B108.2C17—C14—C9112.2 (8)
C3—C4—C5111.3 (8)C15—C14—C9110.3 (7)
C3—C4—H4A109.4C16—C14—C9109.4 (7)
C5—C4—H4A109.4C14—C15—H15A109.5
C3—C4—H4B109.4C14—C15—H15B109.5
C5—C4—H4B109.4H15A—C15—H15B109.5
H4A—C4—H4B108.0C14—C15—H15C109.5
N1—C5—C4110.1 (7)H15A—C15—H15C109.5
N1—C5—H5A109.6H15B—C15—H15C109.5
C4—C5—H5A109.6C14—C16—H16A109.5
N1—C5—H5B109.6C14—C16—H16B109.5
C4—C5—H5B109.6H16A—C16—H16B109.5
H5A—C5—H5B108.2C14—C16—H16C109.5
C7—C6—N1113.0 (7)H16A—C16—H16C109.5
C7—C6—H6A109.0H16B—C16—H16C109.5
N1—C6—H6A109.0C14—C17—H17A109.5
C7—C6—H6B109.0C14—C17—H17B109.5
N1—C6—H6B109.0H17A—C17—H17B109.5
H6A—C6—H6B107.8C14—C17—H17C109.5
C12—C7—C8120.2 (9)H17A—C17—H17C109.5
C12—C7—C6119.9 (9)H17B—C17—H17C109.5
C8—C7—C6119.9 (9)C1—N1—C5112.2 (6)
O1—C8—C7117.9 (8)C1—N1—C6109.6 (6)
O1—C8—C9122.0 (8)C5—N1—C6110.7 (7)
C7—C8—C9120.1 (9)C1—N1—H1C108.0
C10—C9—C8116.8 (9)C5—N1—H1C108.0
C10—C9—C14121.7 (9)C6—N1—H1C108.0
C8—C9—C14121.4 (9)C8—O1—H1109.5
C9—C10—C11123.4 (9)
N1—C1—C2—C356.3 (10)C9—C10—C11—C13177.6 (10)
C1—C2—C3—C457.8 (13)C10—C11—C12—C74.0 (15)
C2—C3—C4—C558.5 (13)C13—C11—C12—C7176.6 (10)
C3—C4—C5—N157.5 (12)C8—C7—C12—C112.3 (14)
N1—C6—C7—C12100.2 (10)C6—C7—C12—C11178.0 (9)
N1—C6—C7—C884.1 (10)C10—C9—C14—C172.9 (12)
C12—C7—C8—O1179.8 (8)C8—C9—C14—C17176.4 (7)
C6—C7—C8—O14.6 (12)C10—C9—C14—C15123.7 (9)
C12—C7—C8—C90.6 (13)C8—C9—C14—C1555.7 (11)
C6—C7—C8—C9175.0 (7)C10—C9—C14—C16115.8 (10)
O1—C8—C9—C10178.9 (8)C8—C9—C14—C1664.9 (10)
C7—C8—C9—C101.6 (12)C2—C1—N1—C556.1 (9)
O1—C8—C9—C141.7 (12)C2—C1—N1—C6179.6 (7)
C7—C8—C9—C14177.8 (8)C4—C5—N1—C156.4 (9)
C8—C9—C10—C110.3 (13)C4—C5—N1—C6179.2 (7)
C14—C9—C10—C11179.7 (9)C7—C6—N1—C1168.6 (7)
C9—C10—C11—C123.1 (15)C7—C6—N1—C567.0 (10)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1C···Br1i0.912.433.332 (8)170
O1—H1···Br1i0.822.423.235 (9)174
Symmetry code: (i) x+1, y+1/2, z+1/2.
 

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