2-[(4-Carboxy­cyclo­hexyl)methyl­ammonio­meth­yl]phenolate

The title compound, C₁₅H₁₉NO₃, a Schiff base, crystallizes as a zwitterion with the hydroxyl H atom transfered to the imine N atom. This leads to the formation of an intra­molecular N—H...O hydrogen bond. In the crystal structure, symmetry-related mol­ecules are linked by an inter­molecular O—H...O hydrogen bond, forming chains extended in the a-axis direction. The mol­ecules are also connected via C—H...O hydrogen bonds, forming a two-dimensional network.

Key indicators

• Single-crystal X-ray study
• T = 173 K
• Mean [sigma](C-C)= 0.002 Å
• R factor = 0.040
• wR factor = 0.153
• Data-to-parameter ratio = 10.7

checkCIF/PLATON results

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Computing details

Data collection: EXPOSE in IPDS-I (Stoe & Cie, 2000); cell refinement: CELL in IPDS-I; data reduction: INTEGRATE in IPDS-I; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: SHELXL97.

2-[(4-carboxycyclohexyl)methylammoniomethyl]phenolate

Crystal data

C15H19NO3	F(000) = 560
Mr = 261.31	Dx = 1.254 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 8000 reflections
a = 9.7519 (13) Å	θ = 2.2–25.8°
b = 12.3306 (12) Å	µ = 0.09 mm^−1
c = 11.5569 (18) Å	T = 173 K
β = 95.020 (17)°	Block, yellow
V = 1384.3 (3) Å^3	0.50 × 0.50 × 0.50 mm
Z = 4

Data collection

Stoe IPDS diffractometer	2130 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.057
Graphite monochromator	θmax = 25.9°, θmin = 2.1°
Detector resolution: 6.67 pixels mm^-1	h = −11→11
φ scans	k = −15→15
10710 measured reflections	l = −14→14
2650 independent reflections

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)] = 0.040	Hydrogen site location: difference Fourier map
wR(F^2) = 0.153	All H-atom parameters refined
S = 1.12	w = 1/[σ^2(Fo^2) + (0.1104P)^2] where P = (Fo^2 + 2Fc^2)/3
2650 reflections	(Δ/σ)max = 0.001
248 parameters	Δρmax = 0.29 e Å^−3
0 restraints	Δρmin = −0.31 e Å^−3

Special details

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

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 (Ų)

	x	y	z	Uiso*/Ueq
O1	1.01769 (12)	0.21245 (9)	0.02322 (9)	0.0268 (3)
O2	0.34728 (14)	0.32845 (9)	0.48201 (14)	0.0430 (5)
O3	0.22777 (12)	0.17514 (9)	0.48895 (12)	0.0340 (4)
N1	0.86319 (14)	0.10078 (10)	0.15406 (11)	0.0234 (4)
C1	0.86013 (16)	0.07794 (11)	−0.05170 (13)	0.0221 (4)
C2	0.96303 (16)	0.15862 (11)	−0.06527 (14)	0.0217 (4)
C3	1.00099 (17)	0.17483 (12)	−0.17989 (14)	0.0250 (5)
C4	0.93960 (18)	0.11781 (13)	−0.27199 (14)	0.0282 (5)
C5	0.83801 (19)	0.03967 (14)	−0.25749 (15)	0.0312 (5)
C6	0.80023 (18)	0.02024 (13)	−0.14805 (14)	0.0284 (5)
C7	0.81901 (16)	0.05116 (12)	0.05995 (14)	0.0232 (5)
C8	0.82602 (17)	0.07308 (13)	0.27020 (14)	0.0254 (5)
C9	0.70969 (16)	0.14269 (12)	0.31096 (13)	0.0210 (4)
C10	0.70695 (17)	0.12561 (13)	0.44165 (14)	0.0257 (5)
C11	0.59036 (17)	0.18974 (14)	0.49033 (14)	0.0270 (5)
C12	0.45247 (16)	0.16356 (12)	0.42613 (14)	0.0235 (5)
C13	0.45649 (18)	0.18410 (13)	0.29512 (14)	0.0257 (5)
C14	0.57053 (17)	0.11647 (13)	0.24752 (14)	0.0241 (5)
C15	0.33795 (18)	0.23126 (12)	0.46956 (14)	0.0261 (5)
H1	0.925 (2)	0.1567 (16)	0.1418 (17)	0.033 (5)*
H3	0.157 (3)	0.225 (2)	0.509 (2)	0.063 (7)*
H3A	1.0728 (19)	0.2293 (15)	−0.1906 (15)	0.025 (4)*
H4A	0.969 (2)	0.1307 (15)	−0.3491 (18)	0.034 (5)*
H5A	0.798 (2)	−0.0036 (17)	−0.3271 (19)	0.041 (5)*
H6A	0.733 (2)	−0.0346 (17)	−0.1330 (18)	0.038 (5)*
H7A	0.757 (2)	−0.0109 (17)	0.0669 (16)	0.031 (5)*
H8A	0.915 (2)	0.0841 (16)	0.3273 (17)	0.032 (5)*
H8B	0.796 (2)	−0.0035 (16)	0.2687 (16)	0.030 (5)*
H9A	0.7315 (18)	0.2200 (15)	0.2970 (15)	0.021 (4)*
H10A	0.804 (2)	0.1493 (17)	0.4854 (18)	0.041 (5)*
H10B	0.694 (2)	0.0482 (17)	0.4554 (17)	0.029 (5)*
H11A	0.591 (2)	0.1745 (16)	0.5745 (19)	0.036 (5)*
H11B	0.611 (2)	0.2693 (17)	0.4805 (18)	0.034 (5)*
H12A	0.4285 (19)	0.0856 (16)	0.4372 (15)	0.025 (4)*
H13A	0.362 (2)	0.1674 (16)	0.2496 (17)	0.036 (5)*
H13B	0.474 (2)	0.2603 (18)	0.2829 (18)	0.039 (5)*
H14A	0.570 (2)	0.1293 (16)	0.1649 (18)	0.033 (5)*
H14B	0.551 (2)	0.0400 (17)	0.2620 (16)	0.031 (5)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0257 (6)	0.0264 (6)	0.0299 (6)	−0.0068 (4)	0.0110 (5)	−0.0056 (4)
O2	0.0352 (8)	0.0233 (7)	0.0729 (10)	0.0028 (5)	0.0177 (7)	−0.0091 (6)
O3	0.0260 (7)	0.0259 (6)	0.0526 (8)	0.0045 (5)	0.0185 (6)	0.0029 (5)
N1	0.0243 (7)	0.0213 (6)	0.0263 (7)	−0.0008 (5)	0.0120 (6)	−0.0001 (5)
C1	0.0222 (8)	0.0186 (7)	0.0264 (8)	0.0017 (6)	0.0065 (7)	0.0003 (6)
C2	0.0204 (8)	0.0184 (7)	0.0271 (8)	0.0036 (6)	0.0072 (6)	−0.0002 (6)
C3	0.0256 (9)	0.0207 (7)	0.0302 (8)	0.0026 (6)	0.0106 (7)	0.0043 (6)
C4	0.0333 (10)	0.0276 (8)	0.0246 (8)	0.0079 (6)	0.0073 (7)	0.0047 (6)
C5	0.0379 (10)	0.0301 (9)	0.0254 (8)	0.0013 (7)	0.0009 (8)	−0.0011 (7)
C6	0.0313 (9)	0.0236 (8)	0.0308 (9)	−0.0045 (7)	0.0048 (7)	−0.0010 (6)
C7	0.0215 (8)	0.0183 (7)	0.0309 (9)	0.0004 (6)	0.0088 (7)	−0.0004 (6)
C8	0.0275 (9)	0.0252 (8)	0.0248 (8)	0.0029 (6)	0.0103 (7)	0.0033 (6)
C9	0.0215 (8)	0.0205 (7)	0.0221 (7)	−0.0001 (6)	0.0074 (6)	0.0011 (6)
C10	0.0254 (9)	0.0302 (9)	0.0221 (8)	0.0035 (6)	0.0056 (7)	0.0020 (6)
C11	0.0282 (9)	0.0321 (9)	0.0216 (8)	0.0035 (6)	0.0068 (7)	−0.0026 (6)
C12	0.0237 (9)	0.0185 (7)	0.0295 (8)	0.0016 (6)	0.0092 (7)	−0.0001 (6)
C13	0.0240 (9)	0.0270 (8)	0.0262 (8)	0.0025 (6)	0.0030 (7)	−0.0009 (6)
C14	0.0241 (9)	0.0257 (8)	0.0228 (8)	0.0001 (6)	0.0038 (7)	−0.0029 (6)
C15	0.0283 (9)	0.0224 (8)	0.0285 (8)	0.0039 (6)	0.0081 (7)	0.0003 (6)

Geometric parameters (Å, º)

O1—C2	1.2943 (19)	C12—C15	1.515 (2)
O2—C15	1.2095 (19)	C13—C14	1.530 (2)
O3—C15	1.314 (2)	C3—H3A	0.986 (19)
O3—H3	0.97 (3)	C4—H4A	0.97 (2)
N1—C7	1.289 (2)	C5—H5A	1.01 (2)
N1—C8	1.461 (2)	C6—H6A	0.97 (2)
N1—H1	0.94 (2)	C7—H7A	0.98 (2)
C1—C7	1.423 (2)	C8—H8A	1.05 (2)
C1—C6	1.405 (2)	C8—H8B	0.99 (2)
C1—C2	1.431 (2)	C9—H9A	0.993 (19)
C2—C3	1.420 (2)	C10—H10A	1.07 (2)
C3—C4	1.369 (2)	C10—H10B	0.98 (2)
C4—C5	1.403 (2)	C11—H11A	0.99 (2)
C5—C6	1.369 (2)	C11—H11B	1.01 (2)
C8—C9	1.529 (2)	C12—H12A	1.00 (2)
C9—C14	1.520 (2)	C13—H13A	1.04 (2)
C9—C10	1.528 (2)	C13—H13B	0.97 (2)
C10—C11	1.532 (2)	C14—H14A	0.97 (2)
C11—C12	1.513 (2)	C14—H14B	0.98 (2)
C12—C13	1.539 (2)
O1···N1	2.6175 (18)	H1···O1	1.84 (2)
O1···C15^i	3.311 (2)	H1···C2	2.45 (2)
O1···O3^i	2.5332 (17)	H1···C3^ii	2.97 (2)
O1···C4^ii	3.298 (2)	H1···C4^ii	2.95 (2)
O2···C7^iii	3.205 (2)	H3···O1^iv	1.58 (3)
O3···O1^iv	2.5332 (17)	H3···C2^iv	2.47 (3)
O3···C2^iv	3.313 (2)	H3···C3^iv	2.83 (2)
O3···C3^iv	3.371 (2)	H3···H3A^iv	2.45 (3)
O1···H4A^ii	2.503 (19)	H3A···O3^i	2.726 (18)
O1···H1	1.84 (2)	H3A···C15^i	3.084 (18)
O1···H10A^v	2.70 (2)	H3A···H3^i	2.45 (3)
O1···H3^i	1.58 (3)	H4A···H10A^x	2.40 (3)
O2···H7A^iii	2.28 (2)	H4A···O1^v	2.503 (19)
O2···H13B	2.83 (2)	H5A···O3^vi	2.82 (2)
O2···H6A^iii	2.60 (2)	H6A···H7A	2.32 (3)
O2···H11B	2.68 (2)	H6A···O2^ix	2.60 (2)
O3···H5A^vi	2.82 (2)	H6A···H13A^vi	2.27 (3)
O3···H10B^vii	2.91 (2)	H7A···H6A	2.32 (3)
O3···H3A^iv	2.726 (18)	H7A···H8B	2.33 (3)
N1···O1	2.6175 (18)	H7A···O2^ix	2.28 (2)
N1···H14A	2.89 (2)	H8A···H10A	2.35 (3)
C1···C1^viii	3.463 (2)	H8A···C4^viii	2.96 (2)
C1···C2^viii	3.592 (2)	H8A···C5^viii	3.02 (2)
C1···C7^viii	3.519 (2)	H8A···C3^ii	3.09 (2)
C2···O3^i	3.313 (2)	H8B···H7A	2.33 (3)
C2···C1^viii	3.592 (2)	H8B···H10B	2.54 (3)
C2···C7^viii	3.345 (2)	H8B···H14B	2.44 (3)
C3···C7^viii	3.513 (2)	H8B···C4^viii	2.94 (2)
C3···O3^i	3.371 (2)	H9A···H11B	2.59 (3)
C3···C8^v	3.569 (2)	H9A···H13B	2.55 (3)
C4···O1^v	3.298 (2)	H9A···C2^ii	3.040 (18)
C4···C8^viii	3.280 (2)	H9A···C3^ii	2.922 (18)
C5···C8^viii	3.574 (3)	H9A···C4^ii	3.006 (18)
C7···C1^viii	3.519 (2)	H10A···C4^xi	3.02 (2)
C7···C14	3.484 (2)	H10A···H4A^xi	2.40 (3)
C7···O2^ix	3.205 (2)	H10A···H8A	2.35 (3)
C7···C2^viii	3.345 (2)	H10A···O1^ii	2.70 (2)
C7···C3^viii	3.513 (2)	H10A···C2^ii	2.92 (2)
C8···C3^ii	3.569 (2)	H10B···H8B	2.54 (3)
C8···C4^viii	3.280 (2)	H10B···H14B	2.53 (3)
C8···C5^viii	3.574 (3)	H10B···O3^vii	2.91 (2)
C14···C7	3.484 (2)	H10B···H12A^vii	2.44 (3)
C15···O1^iv	3.311 (2)	H11B···O2	2.68 (2)
C2···H1	2.45 (2)	H11B···H9A	2.59 (3)
C2···H3^i	2.47 (3)	H11B···H13B	2.55 (3)
C2···H10A^v	2.92 (2)	H11B···C7^ii	3.09 (2)
C2···H9A^v	3.040 (18)	H11B···H14A^ii	2.53 (3)
C3···H3^i	2.83 (3)	H12A···H14B	2.50 (3)
C3···H1^v	2.97 (2)	H12A···H10B^vii	2.44 (3)
C3···H9A^v	2.922 (18)	H13A···C6^vi	2.99 (2)
C3···H8A^v	3.09 (2)	H13A···H6A^vi	2.27 (3)
C4···H10A^x	3.02 (2)	H13B···O2	2.83 (2)
C4···H8B^viii	2.94 (2)	H13B···H9A	2.55 (3)
C4···H9A^v	3.006 (18)	H13B···H11B	2.55 (3)
C4···H1^v	2.95 (2)	H14A···N1	2.89 (2)
C4···H8A^viii	2.96 (2)	H14A···C7	2.97 (2)
C5···H8A^viii	3.02 (2)	H14A···C11^v	3.03 (2)
C6···H13A^vi	2.99 (2)	H14A···H11B^v	2.53 (3)
C7···H14A	2.97 (2)	H14B···H8B	2.44 (3)
C7···H11B^v	3.09 (2)	H14B···H10B	2.53 (3)
C11···H14A^ii	3.03 (2)	H14B···H12A	2.50 (3)
C15···H3A^iv	3.084 (18)
C15—O3—H3	108.5 (16)	C1—C6—H6A	116.9 (12)
C7—N1—C8	124.95 (14)	C5—C6—H6A	122.0 (12)
C7—N1—H1	113.3 (12)	N1—C7—H7A	117.6 (11)
C8—N1—H1	121.8 (12)	C1—C7—H7A	118.6 (11)
C2—C1—C6	120.80 (14)	N1—C8—H8A	106.8 (11)
C2—C1—C7	121.10 (14)	N1—C8—H8B	107.7 (11)
C6—C1—C7	118.07 (14)	C9—C8—H8A	109.1 (11)
C1—C2—C3	116.26 (14)	C9—C8—H8B	108.4 (11)
O1—C2—C1	120.94 (14)	H8A—C8—H8B	111.2 (16)
O1—C2—C3	122.81 (14)	C8—C9—H9A	108.3 (10)
C2—C3—C4	121.39 (15)	C10—C9—H9A	108.4 (10)
C3—C4—C5	121.69 (15)	C14—C9—H9A	108.7 (10)
C4—C5—C6	118.73 (16)	C9—C10—H10A	109.7 (11)
C1—C6—C5	121.12 (16)	C9—C10—H10B	108.0 (12)
N1—C7—C1	123.72 (14)	C11—C10—H10A	109.8 (11)
N1—C8—C9	113.71 (13)	C11—C10—H10B	109.5 (12)
C10—C9—C14	110.83 (13)	H10A—C10—H10B	108.1 (16)
C8—C9—C14	112.78 (13)	C10—C11—H11A	108.8 (11)
C8—C9—C10	107.75 (13)	C10—C11—H11B	107.4 (11)
C9—C10—C11	111.70 (13)	C12—C11—H11A	111.7 (11)
C10—C11—C12	111.48 (13)	C12—C11—H11B	109.2 (11)
C11—C12—C13	110.45 (13)	H11A—C11—H11B	108.1 (17)
C11—C12—C15	111.68 (13)	C11—C12—H12A	110.5 (11)
C13—C12—C15	108.56 (13)	C13—C12—H12A	108.1 (10)
C12—C13—C14	110.23 (13)	C15—C12—H12A	107.5 (11)
C9—C14—C13	110.92 (13)	C12—C13—H13A	111.5 (11)
O2—C15—O3	123.77 (16)	C12—C13—H13B	108.9 (12)
O2—C15—C12	122.38 (16)	C14—C13—H13A	110.5 (11)
O3—C15—C12	113.83 (13)	C14—C13—H13B	109.5 (12)
C2—C3—H3A	117.3 (10)	H13A—C13—H13B	106.2 (16)
C4—C3—H3A	121.3 (10)	C9—C14—H14A	111.6 (12)
C3—C4—H4A	119.0 (11)	C9—C14—H14B	107.5 (11)
C5—C4—H4A	119.3 (11)	C13—C14—H14A	108.9 (12)
C4—C5—H5A	119.6 (12)	C13—C14—H14B	107.8 (12)
C6—C5—H5A	121.6 (12)	H14A—C14—H14B	110.0 (16)
C7—N1—C8—C9	−97.18 (18)	N1—C8—C9—C14	71.62 (17)
C8—N1—C7—C1	−178.10 (14)	C14—C9—C10—C11	−54.48 (17)
C6—C1—C2—O1	179.50 (14)	C8—C9—C14—C13	177.27 (13)
C6—C1—C2—C3	−0.9 (2)	C8—C9—C10—C11	−178.30 (13)
C7—C1—C2—C3	176.91 (14)	C10—C9—C14—C13	56.38 (17)
C2—C1—C6—C5	−0.2 (2)	C9—C10—C11—C12	54.73 (18)
C7—C1—C2—O1	−2.7 (2)	C10—C11—C12—C13	−55.97 (17)
C6—C1—C7—N1	−177.59 (15)	C10—C11—C12—C15	−176.89 (13)
C2—C1—C7—N1	4.6 (2)	C11—C12—C15—O2	48.3 (2)
C7—C1—C6—C5	−178.09 (16)	C11—C12—C15—O3	−133.46 (15)
O1—C2—C3—C4	−178.92 (15)	C13—C12—C15—O3	104.53 (16)
C1—C2—C3—C4	1.5 (2)	C15—C12—C13—C14	−179.64 (13)
C2—C3—C4—C5	−1.0 (3)	C13—C12—C15—O2	−73.7 (2)
C3—C4—C5—C6	−0.2 (3)	C11—C12—C13—C14	57.61 (17)
C4—C5—C6—C1	0.8 (3)	C12—C13—C14—C9	−57.99 (17)
N1—C8—C9—C10	−165.75 (13)

Symmetry codes: (i) x+1, −y+1/2, z−1/2; (ii) x, −y+1/2, z+1/2; (iii) −x+1, y+1/2, −z+1/2; (iv) x−1, −y+1/2, z+1/2; (v) x, −y+1/2, z−1/2; (vi) −x+1, −y, −z; (vii) −x+1, −y, −z+1; (viii) −x+2, −y, −z; (ix) −x+1, y−1/2, −z+1/2; (x) x, y, z−1; (xi) x, y, z+1.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1	0.94 (2)	1.84 (2)	2.6175 (18)	138.9 (17)
O3—H3···O1^iv	0.97 (3)	1.58 (3)	2.5332 (17)	166 (3)
C4—H4A···O1^v	0.97 (2)	2.503 (19)	3.298 (2)	138.8 (15)
C6—H6A···O2^ix	0.97 (2)	2.60 (2)	3.439 (2)	145.4 (16)
C7—H7A···O2^ix	0.98 (2)	2.28 (2)	3.205 (2)	157.3 (16)

Symmetry codes: (iv) x−1, −y+1/2, z+1/2; (v) x, −y+1/2, z−1/2; (ix) −x+1, y−1/2, −z+1/2.