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The title mol­ecule, C15H18BrNO3, contains a cyclo­hexyl ring in a chair conformation linked to an aromatic ring through an HC=N—CH2 group. The mol­ecular conformation may be partially controlled by an intra­molecular O—H...N hydrogen bond, while the crystal structure is stabilized by inter­molecular O—H...O hydrogen bonds.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807002681/lh2295sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536807002681/lh2295Isup2.hkl
Contains datablock I

CCDC reference: 636749

Key indicators

  • Single-crystal X-ray study
  • T = 173 K
  • Mean [sigma](C-C)= 0.003 Å
  • R factor = 0.032
  • wR factor = 0.084
  • Data-to-parameter ratio = 18.4

checkCIF/PLATON results

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Computing details top

Data collection: COLLECT (Hooft, 1998); cell refinement: DENZO (Otwinowski & Minor, 1997); data reduction: SCALEPACK (Otwinowski & Minor, 1997); program(s) used to solve structure: SAPI91 (Fan, 1991); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPII (Johnson, 1976); software used to prepare material for publication: SHELXL97 (Sheldrick, 1997).

3-[(E)-(5-Bromo-2-hydroxyphenyl)methylideneaminomethyl]cyclohexanecarboxylic acid top
Crystal data top
C15H18BrNO3F(000) = 696
Mr = 340.21Dx = 1.518 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 6399 reflections
a = 9.786 (3) Åθ = 3.7–27.4°
b = 12.589 (5) ŵ = 2.77 mm1
c = 12.475 (4) ÅT = 173 K
β = 104.437 (19)°Prism, yellow
V = 1488.3 (9) Å30.18 × 0.12 × 0.12 mm
Z = 4
Data collection top
Nonius KappaCCD
diffractometer
3364 independent reflections
Radiation source: fine-focus sealed tube2581 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.026
ω and φ scansθmax = 27.4°, θmin = 3.7°
Absorption correction: multi-scan
(SORTAV; Blessing, 1997)
h = 1212
Tmin = 0.623, Tmax = 0.717k = 1616
6399 measured reflectionsl = 1616
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.032Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.084H-atom parameters constrained
S = 1.01 w = 1/[σ2(Fo2) + (0.042P)2 + 0.55P]
where P = (Fo2 + 2Fc2)/3
3364 reflections(Δ/σ)max = 0.001
183 parametersΔρmax = 0.27 e Å3
0 restraintsΔρmin = 0.44 e Å3
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Br10.85654 (2)0.36383 (2)0.21632 (2)0.03943 (10)
O10.25860 (16)0.52441 (13)0.10409 (14)0.0356 (4)
H10.20720.48760.05370.053*
O20.37693 (18)0.04334 (13)0.08120 (15)0.0377 (4)
H20.44560.06210.05640.057*
O30.40383 (18)0.10649 (13)0.00511 (15)0.0400 (4)
N10.19571 (19)0.38028 (14)0.04562 (15)0.0269 (4)
C10.4283 (2)0.39988 (17)0.06781 (17)0.0230 (4)
C20.3920 (2)0.48785 (17)0.12603 (18)0.0256 (5)
C30.4950 (2)0.53774 (18)0.20677 (18)0.0291 (5)
H30.47130.59780.24590.035*
C40.6323 (2)0.50146 (18)0.23311 (18)0.0285 (5)
H40.70260.53770.28850.034*
C50.6674 (2)0.41404 (18)0.17788 (19)0.0270 (5)
C60.5679 (2)0.36364 (17)0.09595 (18)0.0253 (5)
H60.59330.30430.05660.030*
C70.3231 (2)0.34888 (17)0.02046 (18)0.0255 (5)
H70.35160.29100.06000.031*
C80.0935 (2)0.33154 (19)0.13788 (19)0.0282 (5)
H8A0.05600.38480.19240.034*
H8B0.13980.27750.17020.034*
C90.0270 (2)0.27948 (16)0.09968 (17)0.0225 (4)
H90.06250.33090.05660.027*
C100.0215 (2)0.18125 (18)0.02900 (19)0.0273 (5)
H10A0.06100.13120.07090.033*
H10B0.09200.20150.03610.033*
C110.1005 (2)0.12782 (17)0.00621 (18)0.0263 (5)
H11A0.06790.06380.04620.032*
H11B0.13630.17540.05280.032*
C120.2225 (2)0.09961 (18)0.09288 (19)0.0261 (5)
H120.19010.04660.13610.031*
C130.2705 (2)0.19790 (19)0.16482 (19)0.0290 (5)
H13A0.34040.17720.23020.035*
H13B0.31060.24830.12360.035*
C140.1470 (2)0.25083 (18)0.19936 (18)0.0267 (5)
H14A0.18040.31400.24080.032*
H14B0.11200.20200.24530.032*
C150.3435 (2)0.05527 (17)0.05236 (18)0.0251 (5)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Br10.02487 (14)0.04206 (17)0.04836 (17)0.00412 (10)0.00351 (11)0.00440 (12)
O10.0258 (8)0.0351 (10)0.0444 (11)0.0061 (7)0.0057 (7)0.0087 (8)
O20.0388 (10)0.0259 (9)0.0578 (11)0.0103 (7)0.0295 (9)0.0108 (8)
O30.0415 (10)0.0305 (9)0.0584 (12)0.0122 (8)0.0318 (9)0.0147 (8)
N10.0250 (10)0.0270 (10)0.0295 (10)0.0065 (8)0.0080 (8)0.0005 (8)
C10.0254 (11)0.0206 (10)0.0241 (11)0.0025 (8)0.0084 (9)0.0013 (9)
C20.0290 (11)0.0221 (11)0.0277 (11)0.0026 (9)0.0111 (9)0.0032 (9)
C30.0350 (13)0.0255 (12)0.0284 (12)0.0014 (10)0.0110 (10)0.0025 (10)
C40.0314 (12)0.0287 (12)0.0251 (12)0.0039 (9)0.0062 (9)0.0008 (10)
C50.0226 (11)0.0286 (12)0.0304 (12)0.0005 (9)0.0075 (9)0.0035 (10)
C60.0281 (11)0.0229 (11)0.0267 (11)0.0011 (9)0.0101 (9)0.0015 (9)
C70.0282 (12)0.0228 (11)0.0284 (11)0.0064 (9)0.0124 (9)0.0000 (9)
C80.0262 (12)0.0291 (12)0.0291 (12)0.0062 (9)0.0069 (9)0.0003 (10)
C90.0234 (11)0.0204 (11)0.0249 (11)0.0011 (8)0.0083 (9)0.0009 (9)
C100.0208 (11)0.0252 (12)0.0350 (13)0.0001 (9)0.0053 (9)0.0038 (10)
C110.0265 (11)0.0239 (11)0.0298 (12)0.0022 (9)0.0093 (9)0.0044 (9)
C120.0244 (11)0.0240 (11)0.0330 (12)0.0043 (9)0.0130 (9)0.0043 (9)
C130.0224 (11)0.0344 (13)0.0282 (12)0.0043 (9)0.0026 (9)0.0017 (10)
C140.0272 (12)0.0294 (12)0.0242 (11)0.0048 (9)0.0079 (9)0.0020 (9)
C150.0251 (11)0.0220 (11)0.0287 (12)0.0030 (9)0.0078 (9)0.0015 (9)
Geometric parameters (Å, º) top
Br1—C51.901 (2)C8—H8A0.9600
O1—C21.346 (3)C8—H8B0.9600
O1—H10.8400C9—C101.524 (3)
O2—C151.311 (3)C9—C141.526 (3)
O2—H20.8400C9—H90.9600
O3—C151.221 (3)C10—C111.526 (3)
N1—C71.271 (3)C10—H10A0.9600
N1—C81.459 (3)C10—H10B0.9600
C1—C61.400 (3)C11—C121.531 (3)
C1—C21.417 (3)C11—H11A0.9600
C1—C71.456 (3)C11—H11B0.9600
C2—C31.385 (3)C12—C151.506 (3)
C3—C41.378 (3)C12—C131.532 (3)
C3—H30.9600C12—H120.9600
C4—C51.386 (3)C13—C141.533 (3)
C4—H40.9600C13—H13A0.9600
C5—C61.378 (3)C13—H13B0.9600
C6—H60.9600C14—H14A0.9600
C7—H70.9600C14—H14B0.9600
C8—C91.526 (3)
C2—O1—H1109.5C8—C9—H9107.5
C15—O2—H2109.5C9—C10—C11111.8 (2)
C7—N1—C8120.1 (2)C9—C10—H10A109.1
C6—C1—C2118.7 (2)C11—C10—H10A108.5
C6—C1—C7120.5 (2)C9—C10—H10B109.2
C2—C1—C7120.8 (2)C11—C10—H10B108.8
O1—C2—C3119.1 (2)H10A—C10—H10B109.5
O1—C2—C1121.1 (2)C10—C11—C12112.2 (2)
C3—C2—C1119.8 (2)C10—C11—H11A109.7
C4—C3—C2120.8 (2)C12—C11—H11A108.4
C4—C3—H3119.0C10—C11—H11B109.2
C2—C3—H3120.1C12—C11—H11B107.8
C3—C4—C5119.5 (2)H11A—C11—H11B109.5
C3—C4—H4119.7C15—C12—C11109.6 (2)
C5—C4—H4120.8C15—C12—C13110.1 (2)
C6—C5—C4121.1 (2)C11—C12—C13110.4 (2)
C6—C5—Br1119.8 (2)C15—C12—H12109.2
C4—C5—Br1119.0 (2)C11—C12—H12108.3
C5—C6—C1120.1 (2)C13—C12—H12109.1
C5—C6—H6120.8C14—C13—C12111.6 (2)
C1—C6—H6119.1C14—C13—H13A108.9
N1—C7—C1121.0 (2)C12—C13—H13A109.1
N1—C7—H7120.2C14—C13—H13B108.6
C1—C7—H7118.8C12—C13—H13B109.1
N1—C8—C9111.4 (2)H13A—C13—H13B109.5
N1—C8—H8A109.3C9—C14—C13112.0 (2)
C9—C8—H8A109.4C9—C14—H14A109.5
N1—C8—H8B109.1C13—C14—H14A109.0
C9—C8—H8B108.0C9—C14—H14B108.7
H8A—C8—H8B109.5C13—C14—H14B108.2
C10—C9—C14110.2 (2)H14A—C14—H14B109.5
C10—C9—C8112.1 (2)O3—C15—O2122.5 (2)
C14—C9—C8110.2 (2)O3—C15—C12122.5 (2)
C10—C9—H9109.1O2—C15—C12115.0 (2)
C14—C9—H9107.7
C6—C1—C2—O1178.5 (2)N1—C8—C9—C1069.2 (2)
C7—C1—C2—O12.3 (3)N1—C8—C9—C14167.71 (18)
C6—C1—C2—C31.8 (3)C14—C9—C10—C1155.3 (2)
C7—C1—C2—C3177.47 (19)C8—C9—C10—C11178.40 (18)
O1—C2—C3—C4178.8 (2)C9—C10—C11—C1255.5 (2)
C1—C2—C3—C41.4 (3)C10—C11—C12—C15175.57 (18)
C2—C3—C4—C50.1 (3)C10—C11—C12—C1354.1 (2)
C3—C4—C5—C60.9 (3)C15—C12—C13—C14175.10 (18)
C3—C4—C5—Br1179.25 (17)C11—C12—C13—C1453.9 (2)
C4—C5—C6—C10.6 (3)C10—C9—C14—C1355.7 (2)
Br1—C5—C6—C1179.60 (16)C8—C9—C14—C13179.83 (19)
C2—C1—C6—C50.8 (3)C12—C13—C14—C955.7 (3)
C7—C1—C6—C5178.48 (19)C11—C12—C15—O361.2 (3)
C8—N1—C7—C1177.00 (18)C13—C12—C15—O360.5 (3)
C6—C1—C7—N1179.1 (2)C11—C12—C15—O2117.2 (2)
C2—C1—C7—N11.7 (3)C13—C12—C15—O2121.1 (2)
C7—N1—C8—C9119.2 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1···N10.841.822.566 (3)148
O2—H2···O3i0.841.832.674 (2)178
Symmetry code: (i) x1, y, z.
 

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