Crystal structure of 1,4,5,6,7,8,9,10,11,12,13-undeca­hydro­cyclo­dodeca[c]pyrazol-3-ol

Raymond, C.C.; Knopp, M.A.

doi:10.1107/S2056989015016746

organic compounds

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ISSN: 2056-9890

Volume 71| Part 10| October 2015| Pages o752-o753

doi:10.1107/S2056989015016746

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Crystal structure of 1,4,5,6,7,8,9,10,11,12,13-undecahydrocyclododeca[c]pyrazol-3-ol

Casey C. Raymond ^a ^* and Michael A. Knopp ^b

^aDepartment of Chemistry, 296 Shineman Center, SUNY Oswego, Oswego, NY 13126, USA, and ^bEnvironmental Science and Sustainability Department, 307 South Hall, 181 Main St., University of Maine at Presque Isle, Presque Isle, Maine 04769, USA
^*Correspondence e-mail: casey.raymond@oswego.edu

Edited by H. Stoeckli-Evans, University of Neuchâtel, Switzerland (Received 3 September 2015; accepted 7 September 2015; online 12 September 2015)

The title compound, C₁₃H₂₂N₂O, crystallized as a pyrazolol tautomer. The 12-membered macrocycle has a distorted chair conformation. In the crystal, molecules are linked via pairs of O—H⋯N hydrogen bonds, forming inversion dimers. The dimers are linked via N—H⋯π and C—H⋯π interactions, forming slabs parallel to the bc plane.

Keywords: crystal structure; pyrazolol; tautomer; pyrazolone; macrocycle; O—H⋯N hydrogen bond; N—H⋯π interaction.

CCDC reference: 1422925

1. Related literature

The crystal structure of the title compound clarifies the connectivity of a class of pyrazolone-derived materials, specifically revealing a pyrazolol tautomer instead of the expected pyrazolone. For the synthesis of the title compound, see: Silveira et al. (1977 ). For the structure of a similar tautomer, see: Silveira et al. (1980 ). For a review of the chemistry of pyrazolones, pyrazolidones and their derivatives, see: Wiley & Wiley (1964 ).

2. Experimental

2.1. Crystal data

C₁₃H₂₂N₂O
M_r = 222.32
Monoclinic, C 2/c
a = 30.008 (2) Å
b = 7.4764 (5) Å
c = 11.6516 (8) Å
β = 105.4374 (12)°
V = 2519.7 (3) Å³
Z = 8
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 100 K
0.59 × 0.33 × 0.11 mm

2.2. Data collection

Bruker APEX CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2007 ) T_min = 0.871, T_max = 0.992
14420 measured reflections
3845 independent reflections
3383 reflections with I > 2σ(I)
R_int = 0.041

2.3. Refinement

R[F² > 2σ(F²)] = 0.051
wR(F²) = 0.119
S = 1.03
3845 reflections
146 parameters
H-atom parameters constrained
Δρ_max = 0.41 e Å⁻³
Δρ_min = −0.20 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

Cg is the centroid of the pyrazol ring N1/N2/C1–C3.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯N1ⁱ	0.84	1.87	2.7072 (12)	177
N2—H2⋯Cgⁱⁱ	0.88	2.58	3.4429 (11)	166
C6—H6B⋯Cgⁱⁱⁱ	0.99	2.71	3.5734 (13)	147
Symmetry codes: (i) $[-x+{\script{1\over 2}}, -y+{\script{1\over 2}}, -z+1]$ ; (ii) $[-x+{\script{1\over 2}}, y+{\script{1\over 2}}, -z+{\script{3\over 2}}]$ ; (iii) $[x, -y+1, z+{\script{1\over 2}}]$ .

Data collection: APEX2 (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015 ); molecular graphics: Mercury (Macrae et al., 2008 ); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Supporting information

CCDC reference: 1422925

Crystal structure: contains datablocks I, New_Global_Publ_Block. DOI: 10.1107/S2056989015016746/su5204sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S2056989015016746/su5204Isup2.hkl

Supporting information file. DOI: 10.1107/S2056989015016746/su5204Isup3.cdx

Supporting information file. DOI: 10.1107/S2056989015016746/su5204Isup4.cml

checkCIF report

Comment top

The crystal structure of the title compound, Fig. 1, clarifies the connectivity of a class of pyrazolone-derived materials, specifically revealing a pyrzazolol tautomer instead of the expected pyrazolone. The bond lengths and angles support this pyrazolol tautomer in the solid state. The crystal structure reveals a different isomer than originally proposed by by (Silveira et al., 1977). However, it is similar to a tautomer proposed in a subsequent investigation (Silveira et al., 1980).

Specifically, we have determined that the compound of interest contains an alcohol group instead of the postulated ketone. The alcoholic group is also consistent with a positive reaction with iron(III) solutions, yielding a dark purple color (Wiley & Wiley, 1964).

In the crystal, molecules are linked via a pair of O—H···N hydrogen bonds forming inversion dimers (Fig. 2 and Table 1). The dimers are linked via N—H···π and C—H···π interactions forming slabs parallel to the bc plane (Table 1).

Synthesis and crystallization top

The title compound was prepared as described by (Silveira et al., 1977). Colorless crystals were obtained by recrystallization by slow cooling of a saturated, warm ethanol solution.

Refinement details top

The NH and OH H atoms were located in a difference Fourier map. All of the H atoms were placed in calculated positions and refined as riding: O—H = 0.84 Å, N—H = 0.88 Å, C—H = 0.99 Å with U_iso(H) = 1.5U_eq(O) for the OH H atom and 1.2U_eq(N,C) for other H atoms.

Related literature top

The crystal structure of the title compound clarifies the connectivity of a class of pyrazolone-derived materials, specifically revealing a pyrazolol tautomer instead of the expected pyrazolone. For the synthesis of the title compound, see: Silveira et al. (1977). For the structure of a similar tautomer, see: Silveira et al. (1980). For a review of the chemistry of pyrazolones, pyrazolidones and their derivatives, see: Wiley & Wiley (1964).

Computing details top

Data collection: APEX2 (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015); molecular graphics: Mercury (Macrae et al., 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

	Fig. 1. A view of the molecular structure of the title compound, with atom labeling. Displacement ellipsoids are drawn at the 50% probability level.
	Fig. 2. A view along the b axis of the crystal packing of the title compound. Hydrogen bonds are shown as dashed lines (see Table 1), and C-bound H atoms have been omitted for clarity.

1,4,5,6,7,8,9,10,11,12,13-Undecahydrocyclododeca[c]pyrazol-3-ol top

Crystal data top

C₁₃H₂₂N₂O	F(000) = 976
M_r = 222.32	D_x = 1.172 Mg m⁻³
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
a = 30.008 (2) Å	Cell parameters from 9304 reflections
b = 7.4764 (5) Å	θ = 2.8–30.5°
c = 11.6516 (8) Å	µ = 0.08 mm⁻¹
β = 105.4374 (12)°	T = 100 K
V = 2519.7 (3) Å³	Plate, colorless
Z = 8	0.59 × 0.33 × 0.11 mm

Data collection top

Bruker APEX CCD diffractometer	3383 reflections with I > 2σ(I)
ω and phi scans	R_int = 0.041
Absorption correction: multi-scan (SADABS; Bruker, 2007)	θ_max = 30.5°, θ_min = 2.8°
T_min = 0.871, T_max = 0.992	h = −42→42
14420 measured reflections	k = −10→10
3845 independent reflections	l = −16→16

Refinement top

Refinement on F²	0 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.051	H-atom parameters constrained
wR(F²) = 0.119	w = 1/[σ²(F_o²) + (0.0437P)² + 2.2017P] where P = (F_o² + 2F_c²)/3
S = 1.03	(Δ/σ)_max = 0.001
3845 reflections	Δρ_max = 0.41 e Å⁻³
146 parameters	Δρ_min = −0.20 e Å⁻³

Crystal data top

C₁₃H₂₂N₂O	V = 2519.7 (3) Å³
M_r = 222.32	Z = 8
Monoclinic, C2/c	Mo Kα radiation
a = 30.008 (2) Å	µ = 0.08 mm⁻¹
b = 7.4764 (5) Å	T = 100 K
c = 11.6516 (8) Å	0.59 × 0.33 × 0.11 mm
β = 105.4374 (12)°

Data collection top

Bruker APEX CCD diffractometer	3845 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2007)	3383 reflections with I > 2σ(I)
T_min = 0.871, T_max = 0.992	R_int = 0.041
14420 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.051	0 restraints
wR(F²) = 0.119	H-atom parameters constrained
S = 1.03	Δρ_max = 0.41 e Å⁻³
3845 reflections	Δρ_min = −0.20 e Å⁻³
146 parameters

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
O1	0.29213 (3)	0.05291 (11)	0.56411 (7)	0.02556 (18)
H1	0.2743	0.0908	0.5005	0.038*
N1	0.26539 (3)	0.31282 (13)	0.63710 (8)	0.0237 (2)
N2	0.27474 (3)	0.38692 (13)	0.74851 (8)	0.0249 (2)
H2	0.2628	0.4887	0.7641	0.030*
C1	0.29108 (4)	0.16479 (14)	0.65347 (9)	0.0214 (2)
C2	0.31597 (4)	0.13945 (14)	0.77385 (9)	0.0208 (2)
C3	0.30426 (4)	0.28695 (15)	0.83204 (9)	0.0221 (2)
C4	0.32060 (4)	0.34607 (15)	0.95885 (9)	0.0240 (2)
H4A	0.3412	0.2533	1.0056	0.029*
H4B	0.2937	0.3591	0.9922	0.029*
C5	0.34679 (4)	0.52462 (15)	0.97093 (10)	0.0258 (2)
H5A	0.3241	0.6224	0.9444	0.031*
H5B	0.3674	0.5230	0.9171	0.031*
C6	0.37587 (4)	0.56546 (16)	1.09762 (10)	0.0284 (2)
H6A	0.3889	0.6874	1.0991	0.034*
H6B	0.3554	0.5647	1.1517	0.034*
C7	0.41558 (4)	0.43390 (17)	1.14525 (10)	0.0296 (2)
H7A	0.4026	0.3117	1.1419	0.036*
H7B	0.4302	0.4623	1.2299	0.036*
C8	0.45307 (4)	0.43498 (18)	1.07776 (12)	0.0336 (3)
H8A	0.4392	0.4770	0.9954	0.040*
H8B	0.4774	0.5215	1.1165	0.040*
C9	0.47548 (4)	0.2527 (2)	1.07272 (12)	0.0363 (3)
H9A	0.4882	0.2088	1.1551	0.044*
H9B	0.5017	0.2682	1.0370	0.044*
C10	0.44297 (4)	0.10995 (17)	1.00175 (10)	0.0291 (2)
H10A	0.4592	−0.0065	1.0134	0.035*
H10B	0.4159	0.0992	1.0346	0.035*
C11	0.42583 (4)	0.14687 (16)	0.86845 (10)	0.0263 (2)
H11A	0.4529	0.1628	0.8359	0.032*
H11B	0.4082	0.2603	0.8563	0.032*
C12	0.39528 (4)	−0.00152 (16)	0.79927 (10)	0.0266 (2)
H12A	0.4114	−0.1172	0.8203	0.032*
H12B	0.3913	0.0185	0.7131	0.032*
C13	0.34726 (4)	−0.01540 (15)	0.82185 (10)	0.0248 (2)
H13A	0.3323	−0.1270	0.7850	0.030*
H13B	0.3511	−0.0241	0.9087	0.030*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0306 (4)	0.0225 (4)	0.0221 (4)	0.0039 (3)	0.0044 (3)	−0.0037 (3)
N1	0.0235 (4)	0.0246 (5)	0.0222 (4)	0.0022 (3)	0.0048 (3)	−0.0047 (3)
N2	0.0259 (4)	0.0248 (5)	0.0227 (4)	0.0054 (4)	0.0044 (3)	−0.0055 (4)
C1	0.0209 (4)	0.0205 (5)	0.0238 (5)	−0.0019 (4)	0.0076 (4)	−0.0018 (4)
C2	0.0222 (4)	0.0189 (5)	0.0219 (5)	−0.0015 (4)	0.0069 (4)	0.0006 (4)
C3	0.0210 (4)	0.0230 (5)	0.0225 (5)	−0.0004 (4)	0.0059 (4)	−0.0001 (4)
C4	0.0286 (5)	0.0230 (5)	0.0207 (5)	0.0016 (4)	0.0069 (4)	−0.0010 (4)
C5	0.0313 (5)	0.0210 (5)	0.0227 (5)	0.0025 (4)	0.0028 (4)	−0.0006 (4)
C6	0.0342 (6)	0.0238 (5)	0.0242 (5)	0.0046 (4)	0.0023 (4)	−0.0052 (4)
C7	0.0342 (6)	0.0298 (6)	0.0220 (5)	0.0067 (5)	0.0026 (4)	−0.0025 (4)
C8	0.0302 (6)	0.0344 (7)	0.0338 (6)	−0.0005 (5)	0.0045 (5)	−0.0064 (5)
C9	0.0291 (6)	0.0442 (8)	0.0317 (6)	0.0084 (5)	0.0013 (5)	−0.0069 (5)
C10	0.0312 (6)	0.0311 (6)	0.0236 (5)	0.0100 (5)	0.0050 (4)	−0.0001 (4)
C11	0.0258 (5)	0.0301 (6)	0.0238 (5)	0.0033 (4)	0.0080 (4)	0.0005 (4)
C12	0.0311 (5)	0.0260 (5)	0.0229 (5)	0.0076 (4)	0.0076 (4)	−0.0010 (4)
C13	0.0312 (5)	0.0176 (5)	0.0254 (5)	0.0011 (4)	0.0072 (4)	0.0015 (4)

Geometric parameters (Å, º) top

O1—C1	1.3424 (13)	C7—H7A	0.9900
O1—H1	0.8400	C7—H7B	0.9900
N1—C1	1.3331 (14)	C8—C9	1.5280 (19)
N1—N2	1.3700 (12)	C8—H8A	0.9900
N2—C3	1.3533 (14)	C8—H8B	0.9900
N2—H2	0.8800	C9—C10	1.5312 (18)
C1—C2	1.4153 (14)	C9—H9A	0.9900
C2—C3	1.3879 (15)	C9—H9B	0.9900
C2—C13	1.5018 (15)	C10—C11	1.5257 (16)
C3—C4	1.4944 (15)	C10—H10A	0.9900
C4—C5	1.5364 (16)	C10—H10B	0.9900
C4—H4A	0.9900	C11—C12	1.5257 (17)
C4—H4B	0.9900	C11—H11A	0.9900
C5—C6	1.5322 (16)	C11—H11B	0.9900
C5—H5A	0.9900	C12—C13	1.5355 (16)
C5—H5B	0.9900	C12—H12A	0.9900
C6—C7	1.5309 (16)	C12—H12B	0.9900
C6—H6A	0.9900	C13—H13A	0.9900
C6—H6B	0.9900	C13—H13B	0.9900
C7—C8	1.5345 (18)

C1—O1—H1	109.5	H7A—C7—H7B	107.6
C1—N1—N2	103.62 (9)	C9—C8—C7	113.91 (12)
C3—N2—N1	112.81 (9)	C9—C8—H8A	108.8
C3—N2—H2	123.6	C7—C8—H8A	108.8
N1—N2—H2	123.6	C9—C8—H8B	108.8
N1—C1—O1	122.57 (10)	C7—C8—H8B	108.8
N1—C1—C2	112.67 (9)	H8A—C8—H8B	107.7
O1—C1—C2	124.76 (10)	C8—C9—C10	114.75 (10)
C3—C2—C1	104.02 (9)	C8—C9—H9A	108.6
C3—C2—C13	130.18 (10)	C10—C9—H9A	108.6
C1—C2—C13	125.80 (10)	C8—C9—H9B	108.6
N2—C3—C2	106.85 (9)	C10—C9—H9B	108.6
N2—C3—C4	121.83 (10)	H9A—C9—H9B	107.6
C2—C3—C4	131.22 (10)	C11—C10—C9	114.67 (11)
C3—C4—C5	111.89 (9)	C11—C10—H10A	108.6
C3—C4—H4A	109.2	C9—C10—H10A	108.6
C5—C4—H4A	109.2	C11—C10—H10B	108.6
C3—C4—H4B	109.2	C9—C10—H10B	108.6
C5—C4—H4B	109.2	H10A—C10—H10B	107.6
H4A—C4—H4B	107.9	C10—C11—C12	113.49 (10)
C4—C5—C6	114.06 (10)	C10—C11—H11A	108.9
C4—C5—H5A	108.7	C12—C11—H11A	108.9
C6—C5—H5A	108.7	C10—C11—H11B	108.9
C4—C5—H5B	108.7	C12—C11—H11B	108.9
C6—C5—H5B	108.7	H11A—C11—H11B	107.7
H5A—C5—H5B	107.6	C11—C12—C13	114.71 (9)
C7—C6—C5	114.20 (9)	C11—C12—H12A	108.6
C7—C6—H6A	108.7	C13—C12—H12A	108.6
C5—C6—H6A	108.7	C11—C12—H12B	108.6
C7—C6—H6B	108.7	C13—C12—H12B	108.6
C5—C6—H6B	108.7	H12A—C12—H12B	107.6
H6A—C6—H6B	107.6	C2—C13—C12	113.98 (9)
C6—C7—C8	114.64 (10)	C2—C13—H13A	108.8
C6—C7—H7A	108.6	C12—C13—H13A	108.8
C8—C7—H7A	108.6	C2—C13—H13B	108.8
C6—C7—H7B	108.6	C12—C13—H13B	108.8
C8—C7—H7B	108.6	H13A—C13—H13B	107.7

C1—N1—N2—C3	−1.49 (12)	N2—C3—C4—C5	−60.38 (14)
N2—N1—C1—O1	−179.34 (10)	C2—C3—C4—C5	115.43 (13)
N2—N1—C1—C2	1.48 (12)	C3—C4—C5—C6	−163.47 (10)
N1—C1—C2—C3	−0.97 (12)	C4—C5—C6—C7	64.21 (14)
O1—C1—C2—C3	179.87 (10)	C5—C6—C7—C8	64.54 (14)
N1—C1—C2—C13	178.86 (10)	C6—C7—C8—C9	−147.20 (11)
O1—C1—C2—C13	−0.30 (17)	C7—C8—C9—C10	65.43 (15)
N1—N2—C3—C2	0.93 (13)	C8—C9—C10—C11	66.47 (15)
N1—N2—C3—C4	177.64 (10)	C9—C10—C11—C12	177.39 (10)
C1—C2—C3—N2	0.01 (11)	C10—C11—C12—C13	70.67 (12)
C13—C2—C3—N2	−179.81 (10)	C3—C2—C13—C12	−101.48 (13)
C1—C2—C3—C4	−176.27 (11)	C1—C2—C13—C12	78.73 (13)
C13—C2—C3—C4	3.91 (19)	C11—C12—C13—C2	68.41 (13)

Hydrogen-bond geometry (Å, º) top

Cg is the centroid of the pyrazol ring N1/N2/C1–C3.

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N1ⁱ	0.84	1.87	2.7072 (12)	177
N2—H2···Cgⁱⁱ	0.88	2.58	3.4429 (11)	166
C6—H6B···Cgⁱⁱⁱ	0.99	2.71	3.5734 (13)	147

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

Hydrogen-bond geometry (Å, º) top

Cg is the centroid of the pyrazol ring N1/N2/C1–C3.

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N1ⁱ	0.84	1.87	2.7072 (12)	177
N2—H2···Cgⁱⁱ	0.88	2.58	3.4429 (11)	166
C6—H6B···Cgⁱⁱⁱ	0.99	2.71	3.5734 (13)	147

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

Acknowledgements

The authors thank M. Zeller and Youngstown State University for the X-ray data collection.

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CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 71| Part 10| October 2015| Pages o752-o753

doi:10.1107/S2056989015016746

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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Crystal structure of 1,4,5,6,7,8,9,10,11,12,13-undeca­hydro­cyclo­dodeca[c]pyrazol-3-ol

1. Related literature

2. Experimental

2.1. Crystal data

2.2. Data collection

2.3. Refinement

Supporting information

Acknowledgements

References

organic compounds

Crystal structure of 1,4,5,6,7,8,9,10,11,12,13-undecahydrocyclododeca[c]pyrazol-3-ol