2-tert-Butyl-4-methyl-6-(1-piperidinio­methyl)­phenol perchlorate

In the crystal structure of the title compound, C₁₇H₂₈NO⁺·ClO₄⁻, the N-protonated piperidine ring is present in the normal chair conformation. The perchlorate anions link the cations, through intermolecular N—H...O and O—H...O hydrogen bonds, forming a chain-like structure.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.005 Å
• R factor = 0.050
• wR factor = 0.130
• Data-to-parameter ratio = 11.8

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry


 Alert Level A:



DIFF_019  Alert A _diffrn_standards_number is missing
          Number of standards used in measurement.

DIFF_020  Alert A _diffrn_standards_interval_count and
          _diffrn_standards_interval_time are missing. Number of measurements
          between standards or time (min) between standards.

DIFF_022  Alert A _diffrn_standards_decay_% is missing
          Percentage decrease in standards intensity.


 3 Alert Level A = Potentially serious problem

 0 Alert Level B = Potential problem

 0 Alert Level C = Please check

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Computing details

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 (Bruker, 1998); software used to prepare material for publication: SHELXL97.

2-tert-Butyl-4-methyl-6-(piperidyl-N-methyl)phenol perchlorate

Crystal data

C17H28NO^+·ClO4^−	F(000) = 776
Mr = 361.85	Dx = 1.264 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 11.639 (5) Å	Cell parameters from 5481 reflections
b = 10.390 (4) Å	θ = 2.4–25.0°
c = 16.466 (6) Å	µ = 0.23 mm^−1
β = 107.297 (7)°	T = 293 K
V = 1901.1 (13) Å^3	Prism, colorless
Z = 4	0.20 × 0.15 × 0.10 mm

Data collection

Bruker SMART 1000 diffractometer	1555 reflections with I > 2σ(I)
ω scans	Rint = 0.041
Absorption correction: multi-scan SAINT (Bruker 1998) and SADABS (Sheldrick, 1997)	θmax = 25.0°
Tmin = 0.956, Tmax = 0.978	h = −7→12
5523 measured reflections	k = −11→11
3256 independent reflections	l = −18→13

Refinement

Refinement on F^2	H-atom parameters constrained
R[F^2 > 2σ(F^2)] = 0.050	w = 1/[σ^2(Fo^2) + (0.06P)^2] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.130	(Δ/σ)max < 0.001
S = 1.03	Δρmax = 0.27 e Å^−3
2656 reflections	Δρmin = −0.22 e Å^−3
226 parameters

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
O1	0.7726 (2)	0.9106 (2)	0.23789 (14)	0.0570 (7)
H1	0.8231	0.8640	0.2272	0.086*
N1	1.0332 (2)	0.7523 (2)	0.40337 (16)	0.0398 (7)
H2	1.0293	0.7381	0.4570	0.048*
C1	1.1383 (3)	0.6783 (4)	0.3938 (2)	0.0563 (10)
H1A	1.1430	0.6888	0.3364	0.068*
H1B	1.1269	0.5875	0.4028	0.068*
C2	1.2550 (3)	0.7229 (4)	0.4564 (3)	0.0729 (13)
H2A	1.3217	0.6758	0.4468	0.087*
H2B	1.2535	0.7051	0.5139	0.087*
C3	1.2731 (3)	0.8660 (5)	0.4466 (3)	0.0763 (13)
H3A	1.3460	0.8940	0.4891	0.092*
H3B	1.2819	0.8831	0.3909	0.092*
C4	1.1664 (3)	0.9399 (4)	0.4572 (3)	0.0739 (13)
H4A	1.1622	0.9285	0.5147	0.089*
H4B	1.1772	1.0310	0.4486	0.089*
C5	1.0502 (3)	0.8948 (3)	0.3946 (2)	0.0532 (10)
H5A	0.9832	0.9408	0.4046	0.064*
H5B	1.0513	0.9137	0.3372	0.064*
C6	0.9174 (3)	0.7042 (3)	0.3425 (2)	0.0420 (9)
H6A	0.9133	0.6115	0.3483	0.050*
H6B	0.9176	0.7224	0.2848	0.050*
C7	0.8076 (3)	0.7640 (3)	0.3571 (2)	0.0380 (8)
C8	0.7403 (3)	0.8604 (3)	0.3054 (2)	0.0377 (8)
C9	0.6360 (3)	0.9113 (3)	0.3199 (2)	0.0375 (8)
C14	0.5591 (3)	1.0149 (3)	0.2621 (2)	0.0452 (9)
C16	0.6341 (3)	1.1380 (3)	0.2647 (3)	0.0694 (12)
H16A	0.6633	1.1686	0.3222	0.104*
H16B	0.5848	1.2029	0.2297	0.104*
H16C	0.7010	1.1190	0.2439	0.104*
C15	0.5108 (3)	0.9650 (4)	0.1704 (2)	0.0677 (12)
H15A	0.4636	0.8889	0.1695	0.102*
H15B	0.5770	0.9449	0.1491	0.102*
H15C	0.4615	1.0300	0.1353	0.102*
C17	0.4494 (3)	1.0524 (4)	0.2893 (3)	0.0722 (12)
H17B	0.4004	0.9777	0.2883	0.108*
H17C	0.4034	1.1160	0.2510	0.108*
H17A	0.4752	1.0870	0.3459	0.108*
C10	0.6062 (3)	0.8625 (3)	0.3888 (2)	0.0440 (9)
H10A	0.5385	0.8959	0.4003	0.053*
C11	0.6702 (3)	0.7670 (4)	0.4421 (2)	0.0465 (9)
C13	0.6316 (3)	0.7175 (4)	0.5163 (2)	0.0714 (13)
H13C	0.6872	0.6527	0.5460	0.107*
H13B	0.5525	0.6811	0.4958	0.107*
H13A	0.6308	0.7873	0.5543	0.107*
C12	0.7698 (3)	0.7183 (3)	0.4247 (2)	0.0452 (9)
H12A	0.8134	0.6530	0.4589	0.054*
Cl1	0.03997 (9)	0.81452 (10)	0.13528 (7)	0.0579 (4)
O2	0.1349 (3)	0.8529 (3)	0.20582 (18)	0.1145 (13)
O3	0.0506 (4)	0.6872 (3)	0.1139 (3)	0.1540 (17)
O4	0.0424 (3)	0.8887 (3)	0.06404 (17)	0.1029 (11)
O5	−0.0700 (3)	0.8373 (5)	0.1497 (2)	0.1450 (17)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0643 (16)	0.0642 (17)	0.0541 (16)	0.0217 (14)	0.0353 (14)	0.0185 (13)
N1	0.0359 (17)	0.0451 (17)	0.0393 (17)	0.0042 (14)	0.0127 (14)	0.0053 (14)
C1	0.046 (2)	0.052 (2)	0.074 (3)	0.015 (2)	0.024 (2)	0.006 (2)
C2	0.038 (3)	0.100 (4)	0.078 (3)	0.016 (2)	0.013 (2)	0.001 (3)
C3	0.039 (2)	0.108 (4)	0.079 (3)	−0.014 (3)	0.014 (2)	−0.011 (3)
C4	0.054 (3)	0.069 (3)	0.095 (3)	−0.015 (2)	0.017 (2)	−0.023 (3)
C5	0.047 (2)	0.044 (2)	0.069 (3)	0.0003 (19)	0.018 (2)	−0.005 (2)
C6	0.040 (2)	0.035 (2)	0.047 (2)	0.0013 (17)	0.0061 (17)	−0.0032 (17)
C7	0.037 (2)	0.037 (2)	0.040 (2)	−0.0013 (17)	0.0110 (18)	−0.0029 (17)
C8	0.040 (2)	0.040 (2)	0.035 (2)	−0.0009 (17)	0.0147 (18)	−0.0017 (17)
C9	0.035 (2)	0.040 (2)	0.037 (2)	−0.0028 (17)	0.0105 (17)	−0.0038 (17)
C14	0.041 (2)	0.045 (2)	0.048 (2)	0.0053 (18)	0.0114 (18)	0.0015 (18)
C16	0.066 (3)	0.041 (2)	0.100 (3)	0.005 (2)	0.022 (2)	0.010 (2)
C15	0.071 (3)	0.068 (3)	0.055 (3)	0.012 (2)	0.005 (2)	0.010 (2)
C17	0.062 (3)	0.074 (3)	0.084 (3)	0.026 (2)	0.025 (2)	0.009 (2)
C10	0.033 (2)	0.055 (2)	0.046 (2)	−0.0026 (18)	0.0144 (18)	−0.0071 (19)
C11	0.039 (2)	0.058 (2)	0.040 (2)	−0.0082 (19)	0.0094 (19)	0.0053 (19)
C13	0.060 (3)	0.103 (4)	0.055 (3)	−0.005 (2)	0.022 (2)	0.017 (2)
C12	0.040 (2)	0.048 (2)	0.042 (2)	−0.0039 (18)	0.0040 (18)	0.0094 (18)
Cl1	0.0667 (7)	0.0591 (7)	0.0526 (7)	0.0129 (6)	0.0248 (6)	0.0008 (5)
O2	0.125 (3)	0.134 (3)	0.055 (2)	0.006 (2)	−0.018 (2)	−0.011 (2)
O3	0.132 (3)	0.053 (2)	0.264 (5)	0.001 (2)	0.039 (3)	−0.035 (3)
O4	0.140 (3)	0.119 (3)	0.0518 (18)	−0.035 (2)	0.0328 (18)	0.0072 (18)
O5	0.105 (3)	0.252 (5)	0.106 (3)	0.072 (3)	0.075 (2)	0.037 (3)

Geometric parameters (Å, º)

O1—C8	1.378 (4)	C9—C10	1.377 (4)
O1—H1	0.8200	C9—C14	1.536 (4)
N1—C1	1.492 (4)	C14—C17	1.524 (5)
N1—C6	1.506 (4)	C14—C15	1.537 (4)
N1—C5	1.506 (4)	C14—C16	1.542 (5)
N1—H2	0.9100	C16—H16A	0.9600
C1—C2	1.512 (5)	C16—H16B	0.9600
C1—H1A	0.9700	C16—H16C	0.9600
C1—H1B	0.9700	C15—H15A	0.9600
C2—C3	1.516 (5)	C15—H15B	0.9600
C2—H2A	0.9700	C15—H15C	0.9600
C2—H2B	0.9700	C17—H17B	0.9600
C3—C4	1.513 (5)	C17—H17C	0.9600
C3—H3A	0.9700	C17—H17A	0.9600
C3—H3B	0.9700	C10—C11	1.387 (4)
C4—C5	1.511 (4)	C10—H10A	0.9300
C4—H4A	0.9700	C11—C12	1.371 (5)
C4—H4B	0.9700	C11—C13	1.512 (5)
C5—H5A	0.9700	C13—H13C	0.9600
C5—H5B	0.9700	C13—H13B	0.9600
C6—C7	1.503 (4)	C13—H13A	0.9600
C6—H6A	0.9700	C12—H12A	0.9300
C6—H6B	0.9700	Cl1—O3	1.384 (3)
C7—C8	1.395 (4)	Cl1—O5	1.390 (3)
C7—C12	1.396 (4)	Cl1—O2	1.402 (3)
C8—C9	1.408 (4)	Cl1—O4	1.411 (3)
C8—O1—H1	109.5	C10—C9—C8	116.3 (3)
C1—N1—C6	111.0 (3)	C10—C9—C14	121.6 (3)
C1—N1—C5	111.2 (3)	C8—C9—C14	122.1 (3)
C6—N1—C5	112.3 (2)	C17—C14—C9	112.4 (3)
C1—N1—H2	107.4	C17—C14—C15	106.3 (3)
C6—N1—H2	107.4	C9—C14—C15	110.4 (3)
C5—N1—H2	107.4	C17—C14—C16	107.3 (3)
N1—C1—C2	111.6 (3)	C9—C14—C16	110.1 (3)
N1—C1—H1A	109.3	C15—C14—C16	110.2 (3)
C2—C1—H1A	109.3	C14—C16—H16A	109.5
N1—C1—H1B	109.3	C14—C16—H16B	109.5
C2—C1—H1B	109.3	H16A—C16—H16B	109.5
H1A—C1—H1B	108.0	C14—C16—H16C	109.5
C1—C2—C3	110.7 (3)	H16A—C16—H16C	109.5
C1—C2—H2A	109.5	H16B—C16—H16C	109.5
C3—C2—H2A	109.5	C14—C15—H15A	109.5
C1—C2—H2B	109.5	C14—C15—H15B	109.5
C3—C2—H2B	109.5	H15A—C15—H15B	109.5
H2A—C2—H2B	108.1	C14—C15—H15C	109.5
C4—C3—C2	109.9 (3)	H15A—C15—H15C	109.5
C4—C3—H3A	109.7	H15B—C15—H15C	109.5
C2—C3—H3A	109.7	C14—C17—H17B	109.5
C4—C3—H3B	109.7	C14—C17—H17C	109.5
C2—C3—H3B	109.7	H17B—C17—H17C	109.5
H3A—C3—H3B	108.2	C14—C17—H17A	109.5
C5—C4—C3	111.3 (3)	H17B—C17—H17A	109.5
C5—C4—H4A	109.4	H17C—C17—H17A	109.5
C3—C4—H4A	109.4	C9—C10—C11	124.4 (3)
C5—C4—H4B	109.4	C9—C10—H10A	117.8
C3—C4—H4B	109.4	C11—C10—H10A	117.8
H4A—C4—H4B	108.0	C12—C11—C10	117.4 (3)
N1—C5—C4	110.9 (3)	C12—C11—C13	121.1 (3)
N1—C5—H5A	109.5	C10—C11—C13	121.5 (3)
C4—C5—H5A	109.5	C11—C13—H13C	109.5
N1—C5—H5B	109.5	C11—C13—H13B	109.5
C4—C5—H5B	109.5	H13C—C13—H13B	109.5
H5A—C5—H5B	108.0	C11—C13—H13A	109.5
N1—C6—C7	113.0 (3)	H13C—C13—H13A	109.5
N1—C6—H6A	109.0	H13B—C13—H13A	109.5
C7—C6—H6A	109.0	C11—C12—C7	121.9 (3)
N1—C6—H6B	109.0	C11—C12—H12A	119.1
C7—C6—H6B	109.0	C7—C12—H12A	119.1
H6A—C6—H6B	107.8	O3—Cl1—O5	111.3 (3)
C8—C7—C12	118.5 (3)	O3—Cl1—O2	112.0 (2)
C8—C7—C6	123.3 (3)	O5—Cl1—O2	110.4 (2)
C12—C7—C6	118.1 (3)	O3—Cl1—O4	106.5 (3)
O1—C8—C7	121.8 (3)	O5—Cl1—O4	107.3 (2)
O1—C8—C9	116.8 (3)	O2—Cl1—O4	109.1 (2)
C7—C8—C9	121.5 (3)
C6—N1—C1—C2	−178.3 (3)	C7—C8—C9—C10	1.4 (5)
C5—N1—C1—C2	55.9 (4)	O1—C8—C9—C14	1.8 (4)
N1—C1—C2—C3	−56.6 (4)	C7—C8—C9—C14	−178.3 (3)
C1—C2—C3—C4	56.4 (4)	C10—C9—C14—C17	−1.1 (4)
C2—C3—C4—C5	−56.7 (5)	C8—C9—C14—C17	178.6 (3)
C1—N1—C5—C4	−55.5 (4)	C10—C9—C14—C15	−119.6 (3)
C6—N1—C5—C4	179.4 (3)	C8—C9—C14—C15	60.1 (4)
C3—C4—C5—N1	56.4 (4)	C10—C9—C14—C16	118.5 (3)
C1—N1—C6—C7	172.7 (3)	C8—C9—C14—C16	−61.8 (4)
C5—N1—C6—C7	−62.1 (4)	C8—C9—C10—C11	−1.3 (5)
N1—C6—C7—C8	103.7 (4)	C14—C9—C10—C11	178.5 (3)
N1—C6—C7—C12	−77.9 (4)	C9—C10—C11—C12	0.0 (5)
C12—C7—C8—O1	179.6 (3)	C9—C10—C11—C13	−179.6 (3)
C6—C7—C8—O1	−2.0 (5)	C10—C11—C12—C7	1.2 (5)
C12—C7—C8—C9	−0.2 (5)	C13—C11—C12—C7	−179.1 (3)
C6—C7—C8—C9	178.2 (3)	C8—C7—C12—C11	−1.1 (5)
O1—C8—C9—C10	−178.5 (3)	C6—C7—C12—C11	−179.6 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O5^i	0.82	2.05	2.761 (4)	145
N1—H2···O4^ii	0.91	2.17	2.998 (5)	151

Symmetry codes: (i) x+1, y, z; (ii) x+1, −y+3/2, z+1/2.