3-[(E)-(5-Bromo-2-hydroxy­phen­yl)methyl­ideneamino­meth­yl]cyclo­hexa­necarboxylic acid

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.

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

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

Crystal data

C15H18BrNO3	F(000) = 696
Mr = 340.21	Dx = 1.518 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 6399 reflections
a = 9.786 (3) Å	θ = 3.7–27.4°
b = 12.589 (5) Å	µ = 2.77 mm^−1
c = 12.475 (4) Å	T = 173 K
β = 104.437 (19)°	Prism, yellow
V = 1488.3 (9) Å^3	0.18 × 0.12 × 0.12 mm
Z = 4

Data collection

Nonius KappaCCD diffractometer	3364 independent reflections
Radiation source: fine-focus sealed tube	2581 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.026
ω and φ scans	θmax = 27.4°, θmin = 3.7°
Absorption correction: multi-scan (SORTAV; Blessing, 1997)	h = −12→12
Tmin = 0.623, Tmax = 0.717	k = −16→16
6399 measured reflections	l = −16→16

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.032	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.084	H-atom parameters constrained
S = 1.01	w = 1/[σ^2(Fo^2) + (0.042P)^2 + 0.55P] where P = (Fo^2 + 2Fc^2)/3
3364 reflections	(Δ/σ)max = 0.001
183 parameters	Δρmax = 0.27 e Å^−3
0 restraints	Δρmin = −0.44 e Å^−3

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
Br1	0.85654 (2)	0.36383 (2)	0.21632 (2)	0.03943 (10)
O1	0.25860 (16)	0.52441 (13)	0.10409 (14)	0.0356 (4)
H1	0.2072	0.4876	0.0537	0.053*
O2	−0.37693 (18)	−0.04334 (13)	−0.08120 (15)	0.0377 (4)
H2	−0.4456	−0.0621	−0.0564	0.057*
O3	−0.40383 (18)	0.10649 (13)	0.00511 (15)	0.0400 (4)
N1	0.19571 (19)	0.38028 (14)	−0.04562 (15)	0.0269 (4)
C1	0.4283 (2)	0.39988 (17)	0.06781 (17)	0.0230 (4)
C2	0.3920 (2)	0.48785 (17)	0.12603 (18)	0.0256 (5)
C3	0.4950 (2)	0.53774 (18)	0.20677 (18)	0.0291 (5)
H3	0.4713	0.5978	0.2459	0.035*
C4	0.6323 (2)	0.50146 (18)	0.23311 (18)	0.0285 (5)
H4	0.7026	0.5377	0.2885	0.034*
C5	0.6674 (2)	0.41404 (18)	0.17788 (19)	0.0270 (5)
C6	0.5679 (2)	0.36364 (17)	0.09595 (18)	0.0253 (5)
H6	0.5933	0.3043	0.0566	0.030*
C7	0.3231 (2)	0.34888 (17)	−0.02046 (18)	0.0255 (5)
H7	0.3516	0.2910	−0.0600	0.031*
C8	0.0935 (2)	0.33154 (19)	−0.13788 (19)	0.0282 (5)
H8A	0.0560	0.3848	−0.1924	0.034*
H8B	0.1398	0.2775	−0.1702	0.034*
C9	−0.0270 (2)	0.27948 (16)	−0.09968 (17)	0.0225 (4)
H9	−0.0625	0.3309	−0.0566	0.027*
C10	0.0215 (2)	0.18125 (18)	−0.02900 (19)	0.0273 (5)
H10A	0.0610	0.1312	−0.0709	0.033*
H10B	0.0920	0.2015	0.0361	0.033*
C11	−0.1005 (2)	0.12782 (17)	0.00621 (18)	0.0263 (5)
H11A	−0.0679	0.0638	0.0462	0.032*
H11B	−0.1363	0.1754	0.0528	0.032*
C12	−0.2225 (2)	0.09961 (18)	−0.09288 (19)	0.0261 (5)
H12	−0.1901	0.0466	−0.1361	0.031*
C13	−0.2705 (2)	0.19790 (19)	−0.16482 (19)	0.0290 (5)
H13A	−0.3404	0.1772	−0.2302	0.035*
H13B	−0.3106	0.2483	−0.1236	0.035*
C14	−0.1470 (2)	0.25083 (18)	−0.19936 (18)	0.0267 (5)
H14A	−0.1804	0.3140	−0.2408	0.032*
H14B	−0.1120	0.2020	−0.2453	0.032*
C15	−0.3435 (2)	0.05527 (17)	−0.05236 (18)	0.0251 (5)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Br1	0.02487 (14)	0.04206 (17)	0.04836 (17)	0.00412 (10)	0.00351 (11)	−0.00440 (12)
O1	0.0258 (8)	0.0351 (10)	0.0444 (11)	0.0061 (7)	0.0057 (7)	−0.0087 (8)
O2	0.0388 (10)	0.0259 (9)	0.0578 (11)	−0.0103 (7)	0.0295 (9)	−0.0108 (8)
O3	0.0415 (10)	0.0305 (9)	0.0584 (12)	−0.0122 (8)	0.0318 (9)	−0.0147 (8)
N1	0.0250 (10)	0.0270 (10)	0.0295 (10)	−0.0065 (8)	0.0080 (8)	−0.0005 (8)
C1	0.0254 (11)	0.0206 (10)	0.0241 (11)	−0.0025 (8)	0.0084 (9)	0.0013 (9)
C2	0.0290 (11)	0.0221 (11)	0.0277 (11)	0.0026 (9)	0.0111 (9)	0.0032 (9)
C3	0.0350 (13)	0.0255 (12)	0.0284 (12)	0.0014 (10)	0.0110 (10)	−0.0025 (10)
C4	0.0314 (12)	0.0287 (12)	0.0251 (12)	−0.0039 (9)	0.0062 (9)	−0.0008 (10)
C5	0.0226 (11)	0.0286 (12)	0.0304 (12)	0.0005 (9)	0.0075 (9)	0.0035 (10)
C6	0.0281 (11)	0.0229 (11)	0.0267 (11)	0.0011 (9)	0.0101 (9)	0.0015 (9)
C7	0.0282 (12)	0.0228 (11)	0.0284 (11)	−0.0064 (9)	0.0124 (9)	0.0000 (9)
C8	0.0262 (12)	0.0291 (12)	0.0291 (12)	−0.0062 (9)	0.0069 (9)	0.0003 (10)
C9	0.0234 (11)	0.0204 (11)	0.0249 (11)	−0.0011 (8)	0.0083 (9)	−0.0009 (9)
C10	0.0208 (11)	0.0252 (12)	0.0350 (13)	−0.0001 (9)	0.0053 (9)	0.0038 (10)
C11	0.0265 (11)	0.0239 (11)	0.0298 (12)	0.0022 (9)	0.0093 (9)	0.0044 (9)
C12	0.0244 (11)	0.0240 (11)	0.0330 (12)	−0.0043 (9)	0.0130 (9)	−0.0043 (9)
C13	0.0224 (11)	0.0344 (13)	0.0282 (12)	−0.0043 (9)	0.0026 (9)	0.0017 (10)
C14	0.0272 (12)	0.0294 (12)	0.0242 (11)	−0.0048 (9)	0.0079 (9)	0.0020 (9)
C15	0.0251 (11)	0.0220 (11)	0.0287 (12)	−0.0030 (9)	0.0078 (9)	−0.0015 (9)

Geometric parameters (Å, º)

Br1—C5	1.901 (2)	C8—H8A	0.9600
O1—C2	1.346 (3)	C8—H8B	0.9600
O1—H1	0.8400	C9—C10	1.524 (3)
O2—C15	1.311 (3)	C9—C14	1.526 (3)
O2—H2	0.8400	C9—H9	0.9600
O3—C15	1.221 (3)	C10—C11	1.526 (3)
N1—C7	1.271 (3)	C10—H10A	0.9600
N1—C8	1.459 (3)	C10—H10B	0.9600
C1—C6	1.400 (3)	C11—C12	1.531 (3)
C1—C2	1.417 (3)	C11—H11A	0.9600
C1—C7	1.456 (3)	C11—H11B	0.9600
C2—C3	1.385 (3)	C12—C15	1.506 (3)
C3—C4	1.378 (3)	C12—C13	1.532 (3)
C3—H3	0.9600	C12—H12	0.9600
C4—C5	1.386 (3)	C13—C14	1.533 (3)
C4—H4	0.9600	C13—H13A	0.9600
C5—C6	1.378 (3)	C13—H13B	0.9600
C6—H6	0.9600	C14—H14A	0.9600
C7—H7	0.9600	C14—H14B	0.9600
C8—C9	1.526 (3)
C2—O1—H1	109.5	C8—C9—H9	107.5
C15—O2—H2	109.5	C9—C10—C11	111.8 (2)
C7—N1—C8	120.1 (2)	C9—C10—H10A	109.1
C6—C1—C2	118.7 (2)	C11—C10—H10A	108.5
C6—C1—C7	120.5 (2)	C9—C10—H10B	109.2
C2—C1—C7	120.8 (2)	C11—C10—H10B	108.8
O1—C2—C3	119.1 (2)	H10A—C10—H10B	109.5
O1—C2—C1	121.1 (2)	C10—C11—C12	112.2 (2)
C3—C2—C1	119.8 (2)	C10—C11—H11A	109.7
C4—C3—C2	120.8 (2)	C12—C11—H11A	108.4
C4—C3—H3	119.0	C10—C11—H11B	109.2
C2—C3—H3	120.1	C12—C11—H11B	107.8
C3—C4—C5	119.5 (2)	H11A—C11—H11B	109.5
C3—C4—H4	119.7	C15—C12—C11	109.6 (2)
C5—C4—H4	120.8	C15—C12—C13	110.1 (2)
C6—C5—C4	121.1 (2)	C11—C12—C13	110.4 (2)
C6—C5—Br1	119.8 (2)	C15—C12—H12	109.2
C4—C5—Br1	119.0 (2)	C11—C12—H12	108.3
C5—C6—C1	120.1 (2)	C13—C12—H12	109.1
C5—C6—H6	120.8	C14—C13—C12	111.6 (2)
C1—C6—H6	119.1	C14—C13—H13A	108.9
N1—C7—C1	121.0 (2)	C12—C13—H13A	109.1
N1—C7—H7	120.2	C14—C13—H13B	108.6
C1—C7—H7	118.8	C12—C13—H13B	109.1
N1—C8—C9	111.4 (2)	H13A—C13—H13B	109.5
N1—C8—H8A	109.3	C9—C14—C13	112.0 (2)
C9—C8—H8A	109.4	C9—C14—H14A	109.5
N1—C8—H8B	109.1	C13—C14—H14A	109.0
C9—C8—H8B	108.0	C9—C14—H14B	108.7
H8A—C8—H8B	109.5	C13—C14—H14B	108.2
C10—C9—C14	110.2 (2)	H14A—C14—H14B	109.5
C10—C9—C8	112.1 (2)	O3—C15—O2	122.5 (2)
C14—C9—C8	110.2 (2)	O3—C15—C12	122.5 (2)
C10—C9—H9	109.1	O2—C15—C12	115.0 (2)
C14—C9—H9	107.7
C6—C1—C2—O1	−178.5 (2)	N1—C8—C9—C10	−69.2 (2)
C7—C1—C2—O1	2.3 (3)	N1—C8—C9—C14	167.71 (18)
C6—C1—C2—C3	1.8 (3)	C14—C9—C10—C11	−55.3 (2)
C7—C1—C2—C3	−177.47 (19)	C8—C9—C10—C11	−178.40 (18)
O1—C2—C3—C4	178.8 (2)	C9—C10—C11—C12	55.5 (2)
C1—C2—C3—C4	−1.4 (3)	C10—C11—C12—C15	−175.57 (18)
C2—C3—C4—C5	0.1 (3)	C10—C11—C12—C13	−54.1 (2)
C3—C4—C5—C6	0.9 (3)	C15—C12—C13—C14	175.10 (18)
C3—C4—C5—Br1	−179.25 (17)	C11—C12—C13—C14	53.9 (2)
C4—C5—C6—C1	−0.6 (3)	C10—C9—C14—C13	55.7 (2)
Br1—C5—C6—C1	179.60 (16)	C8—C9—C14—C13	179.83 (19)
C2—C1—C6—C5	−0.8 (3)	C12—C13—C14—C9	−55.7 (3)
C7—C1—C6—C5	178.48 (19)	C11—C12—C15—O3	61.2 (3)
C8—N1—C7—C1	177.00 (18)	C13—C12—C15—O3	−60.5 (3)
C6—C1—C7—N1	179.1 (2)	C11—C12—C15—O2	−117.2 (2)
C2—C1—C7—N1	−1.7 (3)	C13—C12—C15—O2	121.1 (2)
C7—N1—C8—C9	119.2 (2)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N1	0.84	1.82	2.566 (3)	148
O2—H2···O3^i	0.84	1.83	2.674 (2)	178

Symmetry code: (i) −x−1, −y, −z.