The title compound, racemic 1-[2-(dimethylamino)-1-(4-methoxyphenyl)ethyl]cyclohexanol, C17H27NO2, was precisely characterized at ca 110 K, revealing an intramolecularly hydrogen-bonded structure with different conformational features than those observed earlier in its hydrochloride and hydrobromide derivatives.
Supporting information
CCDC reference: 253030
Key indicators
- Single-crystal X-ray study
- T = 110 K
- Mean (C-C) = 0.002 Å
- R factor = 0.044
- wR factor = 0.121
- Data-to-parameter ratio = 18.5
checkCIF/PLATON results
No syntax errors found
Alert level B
PLAT029_ALERT_3_B _diffrn_measured_fraction_theta_full Low ....... 0.95
Alert level C
REFLT03_ALERT_3_C Reflection count < 95% complete
From the CIF: _diffrn_reflns_theta_max 27.50
From the CIF: _diffrn_reflns_theta_full 0.00
From the CIF: _reflns_number_total 3428
TEST2: Reflns within _diffrn_reflns_theta_max
Count of symmetry unique reflns 3609
Completeness (_total/calc) 94.98%
PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given ....... ?
PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........ 1
0 ALERT level A = In general: serious problem
1 ALERT level B = Potentially serious problem
3 ALERT level C = Check and explain
0 ALERT level G = General alerts; check
0 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
2 ALERT type 3 Indicator that the structure quality may be low
2 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: COLLECT (Nonius, 1999); cell refinement: DENZO (Otwinowski & Minor, 1997); data reduction: DENZO; program(s) used to solve structure: SIR92 (Altomare et al., 1994); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPIII (Burnett & Johnson, 1996); software used to prepare material for publication: SHELXL97.
1-[2-(dimethylamino)-1-(4-methoxyphenyl)ethyl]cyclohexanol
top
Crystal data top
C17H27NO2 | F(000) = 608 |
Mr = 277.40 | Dx = 1.176 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
a = 8.2670 (2) Å | Cell parameters from 3134 reflections |
b = 8.8246 (2) Å | θ = 1.9–27.5° |
c = 21.4946 (6) Å | µ = 0.08 mm−1 |
β = 92.2130 (8)° | T = 110 K |
V = 1566.93 (7) Å3 | Prisms, colorless |
Z = 4 | 0.35 × 0.20 × 0.20 mm |
Data collection top
Nonius KappaCCD diffractometer | 2600 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.028 |
Graphite monochromator | θmax = 27.5°, θmin = 1.9° |
Detector resolution: 56 microns pixels mm-1 | h = −10→10 |
1° φ scans | k = −10→10 |
9690 measured reflections | l = −28→28 |
3428 independent reflections | |
Refinement top
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)] = 0.044 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.121 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.03 | w = 1/[σ2(Fo2) + (0.0599P)2 + 0.3518P] where P = (Fo2 + 2Fc2)/3 |
3428 reflections | (Δ/σ)max < 0.001 |
185 parameters | Δρmax = 0.22 e Å−3 |
0 restraints | Δρmin = −0.20 e Å−3 |
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. 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. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
O1 | 0.68518 (11) | −0.15214 (9) | 0.18884 (4) | 0.0234 (2) | |
HO1 | 0.6409 | −0.1340 | 0.2278 | 0.050 (5)* | |
O2 | 0.35834 (12) | 0.64176 (10) | 0.05879 (4) | 0.0296 (2) | |
N1 | 0.50099 (13) | −0.03900 (12) | 0.28060 (5) | 0.0223 (3) | |
C1 | 0.52138 (18) | −0.00089 (15) | 0.34674 (6) | 0.0284 (3) | |
H1A | 0.4367 | 0.0705 | 0.3581 | 0.043* | |
H1B | 0.6278 | 0.0456 | 0.3546 | 0.043* | |
H1C | 0.5133 | −0.0933 | 0.3717 | 0.043* | |
C2 | 0.34720 (17) | −0.11863 (16) | 0.26944 (7) | 0.0306 (3) | |
H2A | 0.3422 | −0.2059 | 0.2975 | 0.046* | |
H2B | 0.3392 | −0.1536 | 0.2262 | 0.046* | |
H2C | 0.2573 | −0.0496 | 0.2772 | 0.046* | |
C3 | 0.50616 (16) | 0.10170 (14) | 0.24379 (6) | 0.0225 (3) | |
H3A | 0.5985 | 0.1640 | 0.2596 | 0.027* | |
H3B | 0.4058 | 0.1599 | 0.2502 | 0.027* | |
C4 | 0.52309 (15) | 0.07616 (14) | 0.17355 (6) | 0.0212 (3) | |
H4 | 0.4327 | 0.0069 | 0.1600 | 0.025* | |
C5 | 0.68268 (15) | −0.00678 (13) | 0.15785 (6) | 0.0199 (3) | |
C6 | 0.83574 (15) | 0.08175 (14) | 0.17809 (6) | 0.0225 (3) | |
H6A | 0.8326 | 0.1831 | 0.1583 | 0.027* | |
H6B | 0.8379 | 0.0962 | 0.2238 | 0.027* | |
C7 | 0.98988 (16) | −0.00099 (15) | 0.15997 (7) | 0.0264 (3) | |
H7A | 1.0856 | 0.0608 | 0.1725 | 0.032* | |
H7B | 0.9980 | −0.0988 | 0.1824 | 0.032* | |
C8 | 0.98925 (17) | −0.02981 (16) | 0.09030 (7) | 0.0302 (3) | |
H8A | 1.0878 | −0.0868 | 0.0800 | 0.036* | |
H8B | 0.9905 | 0.0681 | 0.0679 | 0.036* | |
C9 | 0.83969 (18) | −0.11982 (15) | 0.06923 (6) | 0.0281 (3) | |
H9A | 0.8451 | −0.2222 | 0.0880 | 0.034* | |
H9B | 0.8380 | −0.1317 | 0.0234 | 0.034* | |
C10 | 0.68374 (16) | −0.04115 (15) | 0.08806 (6) | 0.0238 (3) | |
H10A | 0.6710 | 0.0548 | 0.0645 | 0.029* | |
H10B | 0.5901 | −0.1067 | 0.0766 | 0.029* | |
C11 | 0.49155 (15) | 0.22615 (14) | 0.13972 (6) | 0.0209 (3) | |
C12 | 0.55371 (16) | 0.36498 (14) | 0.16128 (6) | 0.0225 (3) | |
H12 | 0.6281 | 0.3659 | 0.1961 | 0.027* | |
C13 | 0.50973 (16) | 0.50109 (14) | 0.13323 (6) | 0.0227 (3) | |
H13 | 0.5533 | 0.5937 | 0.1489 | 0.027* | |
C14 | 0.40132 (16) | 0.50162 (14) | 0.08191 (6) | 0.0226 (3) | |
C15 | 0.34223 (16) | 0.36566 (15) | 0.05798 (6) | 0.0252 (3) | |
H15 | 0.2719 | 0.3647 | 0.0220 | 0.030* | |
C16 | 0.38719 (16) | 0.23037 (14) | 0.08738 (6) | 0.0246 (3) | |
H16 | 0.3450 | 0.1378 | 0.0711 | 0.030* | |
C17 | 0.24638 (18) | 0.64549 (16) | 0.00686 (7) | 0.0311 (3) | |
H17A | 0.2933 | 0.5938 | −0.0285 | 0.047* | |
H17B | 0.2225 | 0.7510 | −0.0043 | 0.047* | |
H17C | 0.1462 | 0.5942 | 0.0177 | 0.047* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O1 | 0.0287 (5) | 0.0162 (5) | 0.0255 (5) | 0.0028 (3) | 0.0035 (4) | 0.0040 (3) |
O2 | 0.0370 (6) | 0.0202 (5) | 0.0313 (5) | 0.0051 (4) | −0.0017 (4) | 0.0066 (4) |
N1 | 0.0220 (6) | 0.0212 (6) | 0.0236 (6) | −0.0003 (4) | 0.0007 (4) | 0.0036 (4) |
C1 | 0.0310 (8) | 0.0305 (8) | 0.0240 (7) | 0.0042 (6) | 0.0036 (6) | 0.0007 (5) |
C2 | 0.0256 (7) | 0.0310 (8) | 0.0353 (8) | −0.0068 (6) | 0.0020 (6) | 0.0072 (6) |
C3 | 0.0228 (6) | 0.0192 (7) | 0.0257 (7) | 0.0013 (5) | 0.0023 (5) | 0.0015 (5) |
C4 | 0.0198 (6) | 0.0179 (7) | 0.0258 (7) | −0.0004 (5) | −0.0009 (5) | 0.0019 (5) |
C5 | 0.0231 (7) | 0.0145 (6) | 0.0220 (6) | 0.0000 (4) | −0.0003 (5) | 0.0013 (5) |
C6 | 0.0233 (7) | 0.0192 (7) | 0.0249 (7) | −0.0002 (5) | −0.0016 (5) | −0.0017 (5) |
C7 | 0.0219 (7) | 0.0238 (7) | 0.0335 (8) | 0.0000 (5) | 0.0010 (6) | −0.0009 (5) |
C8 | 0.0278 (8) | 0.0291 (8) | 0.0344 (8) | 0.0028 (6) | 0.0090 (6) | 0.0011 (6) |
C9 | 0.0361 (8) | 0.0256 (7) | 0.0229 (7) | 0.0022 (6) | 0.0041 (6) | −0.0024 (5) |
C10 | 0.0295 (7) | 0.0209 (7) | 0.0209 (6) | −0.0005 (5) | −0.0019 (5) | −0.0007 (5) |
C11 | 0.0196 (6) | 0.0193 (7) | 0.0240 (7) | 0.0014 (5) | 0.0021 (5) | 0.0012 (5) |
C12 | 0.0209 (6) | 0.0242 (7) | 0.0221 (6) | 0.0007 (5) | −0.0003 (5) | 0.0005 (5) |
C13 | 0.0234 (7) | 0.0185 (7) | 0.0265 (7) | 0.0000 (5) | 0.0036 (5) | −0.0010 (5) |
C14 | 0.0236 (7) | 0.0196 (7) | 0.0248 (7) | 0.0038 (5) | 0.0034 (5) | 0.0046 (5) |
C15 | 0.0252 (7) | 0.0250 (7) | 0.0250 (7) | 0.0014 (5) | −0.0041 (5) | 0.0020 (5) |
C16 | 0.0256 (7) | 0.0191 (7) | 0.0289 (7) | 0.0004 (5) | −0.0028 (6) | −0.0002 (5) |
C17 | 0.0338 (8) | 0.0297 (8) | 0.0298 (7) | 0.0092 (6) | 0.0007 (6) | 0.0092 (6) |
Geometric parameters (Å, º) top
O1—C5 | 1.4452 (14) | C7—C8 | 1.5188 (19) |
O1—HO1 | 0.9396 | C7—H7A | 0.9900 |
O2—C14 | 1.3744 (15) | C7—H7B | 0.9900 |
O2—C17 | 1.4227 (17) | C8—C9 | 1.524 (2) |
N1—C2 | 1.4644 (17) | C8—H8A | 0.9900 |
N1—C1 | 1.4643 (17) | C8—H8B | 0.9900 |
N1—C3 | 1.4739 (16) | C9—C10 | 1.5324 (19) |
C1—H1A | 0.9800 | C9—H9A | 0.9900 |
C1—H1B | 0.9800 | C9—H9B | 0.9900 |
C1—H1C | 0.9800 | C10—H10A | 0.9900 |
C2—H2A | 0.9800 | C10—H10B | 0.9900 |
C2—H2B | 0.9800 | C11—C16 | 1.3915 (18) |
C2—H2C | 0.9800 | C11—C12 | 1.4006 (18) |
C3—C4 | 1.5382 (18) | C12—C13 | 1.3862 (18) |
C3—H3A | 0.9900 | C12—H12 | 0.9500 |
C3—H3B | 0.9900 | C13—C14 | 1.3943 (19) |
C4—C11 | 1.5279 (17) | C13—H13 | 0.9500 |
C4—C5 | 1.5571 (17) | C14—C15 | 1.3869 (19) |
C4—H4 | 1.0000 | C15—C16 | 1.3946 (18) |
C5—C10 | 1.5308 (18) | C15—H15 | 0.9500 |
C5—C6 | 1.5357 (17) | C16—H16 | 0.9500 |
C6—C7 | 1.5320 (18) | C17—H17A | 0.9800 |
C6—H6A | 0.9900 | C17—H17B | 0.9800 |
C6—H6B | 0.9900 | C17—H17C | 0.9800 |
| | | |
C5—O1—HO1 | 105.1 | C6—C7—H7B | 109.4 |
C14—O2—C17 | 117.12 (10) | H7A—C7—H7B | 108.0 |
C2—N1—C1 | 109.63 (11) | C7—C8—C9 | 110.63 (11) |
C2—N1—C3 | 111.06 (10) | C7—C8—H8A | 109.5 |
C1—N1—C3 | 108.85 (10) | C9—C8—H8A | 109.5 |
N1—C1—H1A | 109.5 | C7—C8—H8B | 109.5 |
N1—C1—H1B | 109.5 | C9—C8—H8B | 109.5 |
H1A—C1—H1B | 109.5 | H8A—C8—H8B | 108.1 |
N1—C1—H1C | 109.5 | C8—C9—C10 | 111.50 (11) |
H1A—C1—H1C | 109.5 | C8—C9—H9A | 109.3 |
H1B—C1—H1C | 109.5 | C10—C9—H9A | 109.3 |
N1—C2—H2A | 109.5 | C8—C9—H9B | 109.3 |
N1—C2—H2B | 109.5 | C10—C9—H9B | 109.3 |
H2A—C2—H2B | 109.5 | H9A—C9—H9B | 108.0 |
N1—C2—H2C | 109.5 | C5—C10—C9 | 112.67 (11) |
H2A—C2—H2C | 109.5 | C5—C10—H10A | 109.1 |
H2B—C2—H2C | 109.5 | C9—C10—H10A | 109.1 |
N1—C3—C4 | 114.15 (10) | C5—C10—H10B | 109.1 |
N1—C3—H3A | 108.7 | C9—C10—H10B | 109.1 |
C4—C3—H3A | 108.7 | H10A—C10—H10B | 107.8 |
N1—C3—H3B | 108.7 | C16—C11—C12 | 116.89 (11) |
C4—C3—H3B | 108.7 | C16—C11—C4 | 119.81 (11) |
H3A—C3—H3B | 107.6 | C12—C11—C4 | 123.14 (11) |
C11—C4—C3 | 108.66 (10) | C13—C12—C11 | 121.83 (12) |
C11—C4—C5 | 115.75 (10) | C13—C12—H12 | 119.1 |
C3—C4—C5 | 113.05 (10) | C11—C12—H12 | 119.1 |
C11—C4—H4 | 106.2 | C12—C13—C14 | 119.79 (11) |
C3—C4—H4 | 106.2 | C12—C13—H13 | 120.1 |
C5—C4—H4 | 106.2 | C14—C13—H13 | 120.1 |
O1—C5—C10 | 105.98 (9) | O2—C14—C15 | 124.19 (12) |
O1—C5—C6 | 108.90 (10) | O2—C14—C13 | 116.00 (11) |
C10—C5—C6 | 110.03 (10) | C15—C14—C13 | 119.80 (11) |
O1—C5—C4 | 108.33 (10) | C14—C15—C16 | 119.26 (12) |
C10—C5—C4 | 110.03 (10) | C14—C15—H15 | 120.4 |
C6—C5—C4 | 113.28 (10) | C16—C15—H15 | 120.4 |
C7—C6—C5 | 111.71 (10) | C11—C16—C15 | 122.37 (12) |
C7—C6—H6A | 109.3 | C11—C16—H16 | 118.8 |
C5—C6—H6A | 109.3 | C15—C16—H16 | 118.8 |
C7—C6—H6B | 109.3 | O2—C17—H17A | 109.5 |
C5—C6—H6B | 109.3 | O2—C17—H17B | 109.5 |
H6A—C6—H6B | 107.9 | H17A—C17—H17B | 109.5 |
C8—C7—C6 | 111.06 (11) | O2—C17—H17C | 109.5 |
C8—C7—H7A | 109.4 | H17A—C17—H17C | 109.5 |
C6—C7—H7A | 109.4 | H17B—C17—H17C | 109.5 |
C8—C7—H7B | 109.4 | | |
| | | |
C2—N1—C3—C4 | −71.74 (14) | C8—C9—C10—C5 | −54.33 (15) |
C1—N1—C3—C4 | 167.47 (10) | C3—C4—C11—C16 | −132.32 (12) |
N1—C3—C4—C11 | 168.31 (10) | C5—C4—C11—C16 | 99.24 (14) |
N1—C3—C4—C5 | −61.75 (14) | C3—C4—C11—C12 | 42.83 (16) |
C11—C4—C5—O1 | −174.40 (10) | C5—C4—C11—C12 | −85.62 (15) |
C3—C4—C5—O1 | 59.35 (13) | C16—C11—C12—C13 | 2.03 (19) |
C11—C4—C5—C10 | −58.96 (14) | C4—C11—C12—C13 | −173.25 (12) |
C3—C4—C5—C10 | 174.79 (10) | C11—C12—C13—C14 | −0.3 (2) |
C11—C4—C5—C6 | 64.67 (14) | C17—O2—C14—C15 | −0.22 (19) |
C3—C4—C5—C6 | −61.58 (14) | C17—O2—C14—C13 | −179.29 (11) |
O1—C5—C6—C7 | 61.24 (13) | C12—C13—C14—O2 | 177.02 (11) |
C10—C5—C6—C7 | −54.52 (14) | C12—C13—C14—C15 | −2.1 (2) |
C4—C5—C6—C7 | −178.15 (10) | O2—C14—C15—C16 | −176.37 (12) |
C5—C6—C7—C8 | 57.27 (14) | C13—C14—C15—C16 | 2.7 (2) |
C6—C7—C8—C9 | −56.99 (15) | C12—C11—C16—C15 | −1.4 (2) |
C7—C8—C9—C10 | 55.39 (15) | C4—C11—C16—C15 | 174.01 (12) |
O1—C5—C10—C9 | −64.37 (13) | C14—C15—C16—C11 | −0.9 (2) |
C6—C5—C10—C9 | 53.22 (14) | N1—C3—C5—O1 | 0.86 (9) |
C4—C5—C10—C9 | 178.72 (10) | | |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O1—HO1···N1 | 0.94 | 1.85 | 2.7272 (14) | 154 |
Comparison of corresponding torsion angles (°) in venlafaxine compounds top | Ia | KIDGUZb,c | WOBMUVb,d | WOBMUV01b,e |
N1—C3—C4—C5 | 61.75 (14) | 144.1 | 144.8 | 137.6 |
N1—C3···C5—O1 | 0.86 (9) | 166.9 | 167.9 | 160.8 |
C3—C4—C5—O1 | 59.35 (13) | 45.7 | 46.2 | 47.2 |