2,6-Bis(3,5-di­methyl­pyrazol-1-yl­methyl)-4-methyl­phenol

The crystal structure of the title compound, C₁₉H₂₄N₄O, has been determined in the monoclinic space group P2₁/c. The two pyrazole substituents are arranged trans to each other; the dihedral angle between them is 83.9 (1)°. There is an intramol­ecular hydrogen bond, with an O...N distance of 2.769 (4) Å, and an intermolecular hydrogen bond, with an O...N distance of 3.197 (4) Å.

Key indicators

• Single-crystal X-ray study
• T = 183 K
• R factor = 0.078
• wR factor = 0.142
• Data-to-parameter ratio = 14.1

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Computing details

Data collection: SMART (Bruker, 2000); cell refinement: SMART; data reduction: SAINT (Bruker, 2000) and SHELXTL/PC (Sheldrick, 1999); program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL/PC; software used to prepare material for publication: SHELXTL/PC.

2,6-Bis(3,5-dimethylpyrazol-1-ylmethyl)-4-methylphenol

Crystal data

C19H24N4O	Dx = 1.238 Mg m^−3
Mr = 324.42	Melting point: 398(K) K
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 9.508 (3) Å	Cell parameters from 8255 reflections
b = 18.747 (6) Å	θ = 2.4–19.6°
c = 10.116 (3) Å	µ = 0.08 mm^−1
β = 105.085 (5)°	T = 183 K
V = 1741.0 (9) Å^3	Layer, colorless
Z = 4	0.2 × 0.2 × 0.1 mm
F(000) = 696

Data collection

Bruker SMART CCD area-detector diffractometer	3053 independent reflections
Radiation source: fine-focus sealed tube	1641 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.066
Detector resolution: 100x100 microns pixels mm^-1	θmax = 25.0°, θmin = 2.2°
Ω scans	h = −10→11
Absorption correction: multi-scan SADABS (Sheldrick, 1996)	k = −22→17
Tmin = 0.984, Tmax = 0.992	l = −11→12
7045 measured 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)] = 0.078	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.142	H-atom parameters constrained
S = 0.98	w = 1/[σ^2(Fo^2) + (0.0393P)^2] where P = (Fo^2 + 2Fc^2)/3
3053 reflections	(Δ/σ)max < 0.001
217 parameters	Δρmax = 0.21 e Å^−3
0 restraints	Δρmin = −0.20 e Å^−3

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
O1	0.2708 (2)	0.08831 (13)	0.5687 (2)	0.0366 (7)
H1	0.2145	0.1115	0.5055	0.055*
N1	0.1360 (3)	0.17047 (17)	0.3439 (3)	0.0335 (8)
N2	0.2350 (3)	0.15631 (17)	0.2719 (3)	0.0315 (8)
N3	0.6118 (3)	0.08598 (19)	0.9238 (3)	0.0364 (8)
N4	0.6772 (3)	0.02299 (18)	0.9730 (3)	0.0401 (9)
C1	−0.0176 (4)	0.2723 (2)	0.3672 (4)	0.0522 (12)
H1A	−0.1030	0.2839	0.2923	0.078*
H1B	0.0224	0.3162	0.4151	0.078*
H1C	−0.0463	0.2398	0.4315	0.078*
C2	0.0948 (4)	0.2375 (2)	0.3107 (4)	0.0342 (10)
C3	0.1690 (4)	0.2652 (2)	0.2222 (4)	0.0398 (10)
H3	0.1598	0.3120	0.1848	0.048*
C4	0.2587 (4)	0.2122 (2)	0.1986 (3)	0.0345 (10)
C5	0.3644 (4)	0.2108 (2)	0.1134 (4)	0.0537 (12)
H5A	0.4623	0.2011	0.1717	0.081*
H5B	0.3639	0.2570	0.0680	0.081*
H5C	0.3369	0.1732	0.0441	0.081*
C6	0.3121 (4)	0.0884 (2)	0.2961 (3)	0.0364 (10)
H6A	0.3501	0.0767	0.2163	0.055*
H6B	0.2433	0.0502	0.3053	0.055*
C7	0.4371 (4)	0.09051 (19)	0.4238 (3)	0.0295 (9)
C8	0.5804 (4)	0.09084 (19)	0.4164 (4)	0.0344 (9)
H8	0.5998	0.0910	0.3289	0.041*
C9	0.6964 (4)	0.09093 (19)	0.5325 (4)	0.0326 (9)
C10	0.6646 (4)	0.08986 (19)	0.6586 (4)	0.0335 (9)
H10	0.7425	0.0901	0.7395	0.040*
C11	0.5225 (4)	0.0884 (2)	0.6706 (3)	0.0301 (9)
C12	0.4094 (4)	0.09049 (19)	0.5520 (4)	0.0293 (9)
C13	0.8517 (3)	0.0902 (2)	0.5213 (4)	0.0454 (11)
H13B	0.9131	0.1179	0.5966	0.068*
H13A	0.8557	0.1113	0.4337	0.068*
H13C	0.8869	0.0409	0.5262	0.068*
C14	0.4862 (4)	0.0847 (2)	0.8074 (3)	0.0411 (11)
H14B	0.4223	0.1254	0.8144	0.062*
H14A	0.4308	0.0403	0.8107	0.062*
C15	0.6394 (4)	0.2176 (2)	0.9457 (4)	0.0600 (13)
H15A	0.5334	0.2216	0.9290	0.090*
H15B	0.6675	0.2294	0.8617	0.090*
H15C	0.6870	0.2506	1.0187	0.090*
C16	0.6853 (4)	0.1431 (2)	0.9878 (4)	0.0420 (11)
C17	0.8017 (4)	0.1164 (2)	1.0833 (4)	0.0477 (12)
H17	0.8744	0.1429	1.1463	0.057*
C18	0.7930 (4)	0.0427 (2)	1.0704 (4)	0.0434 (11)
C19	0.8926 (4)	−0.0130 (3)	1.1507 (4)	0.0702 (15)
H19C	0.8694	−0.0595	1.1058	0.105*
H19B	0.8796	−0.0155	1.2436	0.105*
H19A	0.9938	−0.0006	1.1553	0.105*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0330 (14)	0.0419 (18)	0.0338 (15)	0.0056 (13)	0.0066 (12)	0.0067 (13)
N1	0.0284 (17)	0.039 (2)	0.0323 (19)	0.0064 (16)	0.0067 (15)	0.0067 (16)
N2	0.0354 (19)	0.031 (2)	0.0273 (18)	0.0057 (16)	0.0064 (15)	0.0020 (16)
N3	0.0399 (19)	0.040 (2)	0.0280 (18)	0.0012 (19)	0.0058 (15)	0.0009 (18)
N4	0.043 (2)	0.041 (2)	0.035 (2)	0.0032 (18)	0.0073 (16)	0.0037 (18)
C1	0.051 (3)	0.056 (3)	0.055 (3)	0.015 (2)	0.022 (2)	0.010 (2)
C2	0.031 (2)	0.037 (3)	0.032 (2)	0.003 (2)	0.0042 (18)	0.004 (2)
C3	0.041 (2)	0.034 (3)	0.043 (3)	0.004 (2)	0.009 (2)	0.011 (2)
C4	0.034 (2)	0.045 (3)	0.024 (2)	0.005 (2)	0.0062 (18)	0.010 (2)
C5	0.056 (3)	0.063 (3)	0.046 (3)	0.016 (2)	0.021 (2)	0.020 (2)
C6	0.040 (2)	0.033 (2)	0.033 (2)	0.008 (2)	0.0043 (18)	−0.001 (2)
C7	0.036 (2)	0.023 (2)	0.028 (2)	0.0058 (19)	0.0056 (18)	−0.0009 (18)
C8	0.043 (2)	0.025 (2)	0.036 (2)	0.004 (2)	0.0122 (19)	0.0048 (19)
C9	0.035 (2)	0.024 (2)	0.039 (2)	−0.0034 (19)	0.0101 (19)	0.002 (2)
C10	0.035 (2)	0.031 (2)	0.032 (2)	−0.002 (2)	0.0037 (18)	0.0040 (19)
C11	0.036 (2)	0.026 (2)	0.027 (2)	0.0002 (19)	0.0068 (18)	0.0008 (18)
C12	0.027 (2)	0.020 (2)	0.043 (2)	0.0005 (18)	0.0124 (19)	0.0016 (19)
C13	0.042 (2)	0.049 (3)	0.046 (3)	−0.003 (2)	0.012 (2)	0.001 (2)
C14	0.033 (2)	0.050 (3)	0.038 (2)	0.002 (2)	0.0057 (19)	0.004 (2)
C15	0.065 (3)	0.047 (3)	0.076 (3)	−0.003 (3)	0.033 (3)	−0.006 (3)
C16	0.050 (3)	0.041 (3)	0.041 (3)	−0.005 (2)	0.022 (2)	−0.008 (2)
C17	0.040 (3)	0.067 (4)	0.032 (3)	−0.015 (2)	0.003 (2)	−0.010 (2)
C18	0.042 (3)	0.054 (3)	0.032 (2)	−0.001 (2)	0.004 (2)	0.006 (2)
C19	0.054 (3)	0.094 (4)	0.056 (3)	0.013 (3)	0.003 (2)	0.029 (3)

Geometric parameters (Å, º)

O1—C12	1.372 (4)	C7—C12	1.389 (4)
O1—H1	0.8400	C8—C9	1.386 (4)
N1—C2	1.333 (4)	C8—H8	0.9500
N1—N2	1.358 (3)	C9—C10	1.387 (4)
N2—C4	1.337 (4)	C9—C13	1.509 (4)
N2—C6	1.458 (4)	C10—C11	1.387 (4)
N3—C16	1.348 (5)	C10—H10	0.9500
N3—N4	1.367 (4)	C11—C12	1.387 (4)
N3—C14	1.442 (4)	C11—C14	1.512 (4)
N4—C18	1.325 (4)	C13—H13B	0.9800
C1—C2	1.488 (5)	C13—H13A	0.9800
C1—H1A	0.9800	C13—H13C	0.9800
C1—H1B	0.9800	C14—H14B	0.9900
C1—H1C	0.9800	C14—H14A	0.9900
C2—C3	1.378 (5)	C15—C16	1.492 (5)
C3—C4	1.370 (5)	C15—H15A	0.9800
C3—H3	0.9500	C15—H15B	0.9800
C4—C5	1.485 (4)	C15—H15C	0.9800
C5—H5A	0.9800	C16—C17	1.361 (5)
C5—H5B	0.9800	C17—C18	1.388 (5)
C5—H5C	0.9800	C17—H17	0.9500
C6—C7	1.511 (4)	C18—C19	1.499 (5)
C6—H6A	0.9900	C19—H19C	0.9800
C6—H6B	0.9900	C19—H19B	0.9800
C7—C8	1.384 (4)	C19—H19A	0.9800
C12—O1—H1	109.5	C8—C9—C13	121.0 (3)
C2—N1—N2	104.4 (3)	C9—C10—C11	122.1 (3)
C4—N2—N1	112.6 (3)	C9—C10—H10	119.0
C4—N2—C6	128.9 (3)	C11—C10—H10	119.0
N1—N2—C6	118.0 (3)	C10—C11—C12	118.5 (3)
C16—N3—N4	112.4 (3)	C10—C11—C14	122.7 (3)
C16—N3—C14	128.4 (4)	C12—C11—C14	118.8 (3)
N4—N3—C14	119.0 (3)	O1—C12—C11	116.5 (3)
C18—N4—N3	104.0 (3)	O1—C12—C7	122.4 (3)
C2—C1—H1A	109.5	C11—C12—C7	121.0 (3)
C2—C1—H1B	109.5	C9—C13—H13B	109.5
H1A—C1—H1B	109.5	C9—C13—H13A	109.5
C2—C1—H1C	109.5	H13B—C13—H13A	109.5
H1A—C1—H1C	109.5	C9—C13—H13C	109.5
H1B—C1—H1C	109.5	H13B—C13—H13C	109.5
N1—C2—C3	110.6 (3)	H13A—C13—H13C	109.5
N1—C2—C1	120.7 (3)	N3—C14—C11	114.1 (3)
C3—C2—C1	128.6 (4)	N3—C14—H14B	108.7
C4—C3—C2	106.7 (3)	C11—C14—H14B	108.7
C4—C3—H3	126.7	N3—C14—H14A	108.7
C2—C3—H3	126.7	C11—C14—H14A	108.7
N2—C4—C3	105.7 (3)	H14B—C14—H14A	107.6
N2—C4—C5	123.0 (4)	C16—C15—H15A	109.5
C3—C4—C5	131.3 (4)	C16—C15—H15B	109.5
C4—C5—H5A	109.5	H15A—C15—H15B	109.5
C4—C5—H5B	109.5	C16—C15—H15C	109.5
H5A—C5—H5B	109.5	H15A—C15—H15C	109.5
C4—C5—H5C	109.5	H15B—C15—H15C	109.5
H5A—C5—H5C	109.5	N3—C16—C17	105.9 (4)
H5B—C5—H5C	109.5	N3—C16—C15	122.0 (4)
N2—C6—C7	111.7 (3)	C17—C16—C15	132.1 (4)
N2—C6—H6A	109.3	C16—C17—C18	106.4 (4)
C7—C6—H6A	109.3	C16—C17—H17	126.8
N2—C6—H6B	109.3	C18—C17—H17	126.8
C7—C6—H6B	109.3	N4—C18—C17	111.4 (4)
H6A—C6—H6B	107.9	N4—C18—C19	119.6 (4)
C8—C7—C12	118.6 (3)	C17—C18—C19	129.0 (4)
C8—C7—C6	121.3 (3)	C18—C19—H19C	109.5
C12—C7—C6	120.1 (3)	C18—C19—H19B	109.5
C7—C8—C9	122.2 (3)	H19C—C19—H19B	109.5
C7—C8—H8	118.9	C18—C19—H19A	109.5
C9—C8—H8	118.9	H19C—C19—H19A	109.5
C10—C9—C8	117.6 (3)	H19B—C19—H19A	109.5
C10—C9—C13	121.4 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N1	0.84	1.95	2.769 (4)	163
O1—H1···N2	0.84	2.56	3.197 (4)	133