2,6-Bis(3,4,5-trimethyl­pyrazol-1-ylmeth­yl)pyridine

The title compound, C₁₉H₂₅N₅, adopts pseudo-C₂ symmetry in which the non-substituted N atoms of the pyrazole rings are on opposite sides of the pyridine plane. The packing involves C—H...π, π–π, C—H...N and hydro­phobic CH₃...CH₃ inter­actions, which are responsible for the observed columnar arrangement.

Key indicators

• Single-crystal X-ray study
• T = 298 K
• Mean [sigma](C-C) = 0.009 Å
• R factor = 0.094
• wR factor = 0.295
• Data-to-parameter ratio = 15.0

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT026_ALERT_3_B Ratio Observed / Unique Reflections too Low ....         38 Perc.

Alert level C
RFACR01_ALERT_3_C  The value of the weighted R factor is > 0.25
            Weighted R factor given   0.295
RINTA01_ALERT_3_C  The value of Rint is greater than 0.10
            Rint given   0.130
PLAT020_ALERT_3_C The value of Rint is greater than 0.10 .........       0.13
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical .          ?
PLAT084_ALERT_2_C High R2 Value ..................................       0.30
PLAT152_ALERT_1_C Supplied and Calc Volume s.u. Inconsistent .....          ?
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...          9
PLAT380_ALERT_4_C Check Incorrectly? Oriented X(sp2)-Methyl Moiety        C10
PLAT380_ALERT_4_C Check Incorrectly? Oriented X(sp2)-Methyl Moiety        C11
PLAT380_ALERT_4_C Check Incorrectly? Oriented X(sp2)-Methyl Moiety        C17
PLAT380_ALERT_4_C Check Incorrectly? Oriented X(sp2)-Methyl Moiety        C18
PLAT380_ALERT_4_C Check Incorrectly? Oriented X(sp2)-Methyl Moiety        C19

   0 ALERT level A = In general: serious problem
   1 ALERT level B = Potentially serious problem
  12 ALERT level C = Check and explain
   0 ALERT level G = General alerts; check

   2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   1 ALERT type 2 Indicator that the structure model may be wrong or deficient
   5 ALERT type 3 Indicator that the structure quality may be low
   5 ALERT type 4 Improvement, methodology, query or suggestion

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Computing details

Data collection: MSC/AFC Diffractometer Control Software (Molecular Structure Corporation, 1993); cell refinement: MSC/AFC Diffractometer Control Software; data reduction: TEXSAN (Molecular Structure Corporation, 1999); program(s) used to solve structure: SHELXLTL-NT (Bruker, 1998); program(s) used to refine structure: SHELXLTL-NT; molecular graphics: SHELXLTL-NT; software used to prepare material for publication: SHELXLTL-NT.

2,6-Bis(3,4,5-trimethylpyrazol-1-ylmethyl)pyridine

Crystal data

C19H25N5	F(000) = 696
Mr = 323.44	Dx = 1.158 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 19 reflections
a = 6.7834 (14) Å	θ = 7.3–16.5°
b = 17.953 (4) Å	µ = 0.07 mm^−1
c = 15.247 (3) Å	T = 298 K
β = 92.53 (3)°	Irregular, colourless
V = 1855.0 (6) Å^3	0.40 × 0.30 × 0.20 mm
Z = 4

Data collection

Rigaku AFC-7S diffractometer	1223 reflections with I > 2σ(I)
Radiation source: Normal-focus sealed tube	Rint = 0.130
Graphite monochromator	θmax = 25.0°, θmin = 1.8°
ω–2θ scans	h = 0→8
Absorption correction: ψ scan (North et al., 1968)	k = 0→21
Tmin = 0.972, Tmax = 0.986	l = −18→18
3547 measured reflections	3 standard reflections every 150 reflections
3254 independent reflections	intensity decay: none

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)] = 0.094	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.295	H-atom parameters constrained
S = 0.99	w = 1/[σ^2(Fo^2) + (0.1343P)^2] where P = (Fo^2 + 2Fc^2)/3
3254 reflections	(Δ/σ)max < 0.001
217 parameters	Δρmax = 0.22 e Å^−3
0 restraints	Δρmin = −0.24 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
N1	0.4507 (6)	0.2847 (3)	0.4073 (3)	0.0516 (13)
N2	0.1573 (6)	0.2946 (3)	0.1992 (3)	0.0544 (14)
N3	0.2552 (7)	0.3147 (3)	0.1278 (3)	0.0667 (15)
N4	0.7248 (7)	0.3402 (3)	0.6114 (3)	0.0555 (14)
N5	0.6176 (7)	0.3573 (3)	0.6802 (3)	0.0594 (14)
C1	0.5436 (8)	0.3313 (4)	0.4651 (4)	0.0493 (15)
C2	0.5478 (9)	0.4064 (4)	0.4535 (4)	0.0612 (17)
H2A	0.6152	0.4365	0.4944	0.073*
C3	0.4519 (9)	0.4379 (4)	0.3807 (4)	0.0618 (18)
H3A	0.4538	0.4891	0.3717	0.074*
C4	0.3532 (9)	0.3912 (4)	0.3218 (4)	0.0607 (18)
H4A	0.2839	0.4105	0.2730	0.073*
C5	0.3590 (8)	0.3157 (4)	0.3366 (4)	0.0491 (15)
C6	0.2659 (8)	0.2602 (4)	0.2722 (4)	0.0581 (17)
H6A	0.3689	0.2291	0.2496	0.070*
H6B	0.1773	0.2282	0.3033	0.070*
C7	−0.0283 (8)	0.3228 (4)	0.1976 (4)	0.0565 (17)
C8	−0.0565 (9)	0.3604 (4)	0.1207 (4)	0.0586 (17)
C9	0.1253 (10)	0.3548 (4)	0.0788 (4)	0.0667 (19)
C10	−0.1642 (9)	0.3103 (4)	0.2688 (4)	0.086 (2)
H10A	−0.0986	0.2817	0.3146	0.130*
H10B	−0.2782	0.2835	0.2463	0.130*
H10C	−0.2045	0.3573	0.2919	0.130*
C11	−0.2379 (10)	0.4030 (4)	0.0865 (5)	0.090 (2)
H11A	−0.3407	0.3983	0.1274	0.134*
H11B	−0.2825	0.3829	0.0307	0.134*
H11C	−0.2050	0.4546	0.0797	0.134*
C12	0.1788 (12)	0.3834 (5)	−0.0080 (5)	0.111 (3)
H12A	0.3129	0.3702	−0.0185	0.166*
H12B	0.1654	0.4367	−0.0091	0.166*
H12C	0.0928	0.3620	−0.0529	0.166*
C13	0.6404 (8)	0.2918 (4)	0.5434 (4)	0.0607 (17)
H13A	0.5430	0.2600	0.5692	0.073*
H13B	0.7441	0.2599	0.5228	0.073*
C14	0.7364 (10)	0.3999 (4)	0.7313 (4)	0.0592 (17)
C15	0.9199 (9)	0.4098 (4)	0.6937 (4)	0.0588 (17)
C16	0.9068 (9)	0.3723 (4)	0.6173 (4)	0.0592 (17)
C17	0.6689 (11)	0.4286 (4)	0.8168 (4)	0.091 (2)
H17A	0.5360	0.4124	0.8249	0.137*
H17B	0.6735	0.4820	0.8168	0.137*
H17C	0.7537	0.4098	0.8638	0.137*
C18	1.0911 (10)	0.4555 (4)	0.7320 (5)	0.095 (3)
H18A	1.1989	0.4534	0.6933	0.143*
H18B	1.1325	0.4358	0.7883	0.143*
H18C	1.0501	0.5063	0.7385	0.143*
C19	1.0540 (10)	0.3610 (4)	0.5488 (5)	0.091 (2)
H19A	1.1725	0.3879	0.5648	0.137*
H19B	1.0008	0.3789	0.4934	0.137*
H19C	1.0837	0.3089	0.5442	0.137*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N1	0.045 (3)	0.062 (4)	0.047 (3)	0.001 (3)	0.000 (2)	0.005 (3)
N2	0.040 (3)	0.072 (4)	0.051 (3)	0.001 (3)	−0.003 (2)	−0.006 (3)
N3	0.059 (3)	0.085 (4)	0.056 (3)	0.006 (3)	0.002 (3)	0.008 (3)
N4	0.046 (3)	0.068 (4)	0.051 (3)	−0.005 (3)	−0.005 (2)	0.005 (3)
N5	0.049 (3)	0.077 (4)	0.051 (3)	−0.002 (3)	−0.004 (3)	0.002 (3)
C1	0.040 (3)	0.061 (4)	0.046 (3)	0.003 (3)	−0.004 (3)	−0.002 (3)
C2	0.062 (4)	0.059 (5)	0.061 (4)	0.001 (4)	−0.007 (3)	−0.001 (4)
C3	0.075 (4)	0.047 (4)	0.063 (4)	0.013 (3)	−0.008 (3)	−0.001 (3)
C4	0.056 (4)	0.067 (5)	0.058 (4)	0.012 (3)	−0.013 (3)	0.004 (4)
C5	0.045 (3)	0.053 (4)	0.049 (4)	0.011 (3)	0.004 (3)	0.003 (3)
C6	0.045 (3)	0.070 (5)	0.058 (4)	0.000 (3)	−0.010 (3)	−0.001 (4)
C7	0.040 (3)	0.068 (4)	0.060 (4)	−0.002 (3)	−0.008 (3)	−0.017 (4)
C8	0.054 (4)	0.057 (4)	0.063 (4)	0.004 (3)	−0.021 (3)	−0.009 (4)
C9	0.070 (4)	0.076 (5)	0.053 (4)	0.000 (4)	−0.011 (3)	0.007 (4)
C10	0.053 (4)	0.096 (6)	0.112 (6)	−0.002 (4)	0.020 (4)	−0.007 (5)
C11	0.076 (5)	0.077 (5)	0.111 (6)	0.014 (4)	−0.038 (4)	−0.005 (5)
C12	0.135 (7)	0.117 (8)	0.080 (6)	0.008 (6)	0.010 (5)	0.025 (5)
C13	0.056 (4)	0.064 (4)	0.060 (4)	0.004 (3)	−0.011 (3)	0.002 (4)
C14	0.063 (4)	0.062 (4)	0.051 (4)	0.003 (4)	−0.015 (3)	−0.005 (3)
C15	0.047 (4)	0.066 (5)	0.062 (4)	0.001 (3)	−0.013 (3)	0.003 (4)
C16	0.042 (3)	0.063 (5)	0.073 (5)	0.000 (3)	−0.003 (3)	0.017 (4)
C17	0.097 (5)	0.101 (6)	0.075 (5)	0.000 (5)	−0.011 (4)	−0.016 (5)
C18	0.071 (5)	0.086 (6)	0.127 (6)	−0.016 (4)	−0.023 (4)	−0.012 (5)
C19	0.060 (4)	0.108 (7)	0.107 (6)	0.008 (4)	0.014 (4)	0.009 (5)

Geometric parameters (Å, º)

N1—C5	1.341 (6)	C10—H10A	0.9600
N1—C1	1.351 (7)	C10—H10B	0.9600
N2—N3	1.350 (6)	C10—H10C	0.9600
N2—C7	1.357 (7)	C11—H11A	0.9600
N2—C6	1.445 (6)	C11—H11B	0.9600
N3—C9	1.340 (7)	C11—H11C	0.9600
N4—N5	1.339 (6)	C12—H12A	0.9600
N4—C16	1.361 (7)	C12—H12B	0.9600
N4—C13	1.452 (7)	C12—H12C	0.9600
N5—C14	1.337 (7)	C13—H13A	0.9700
C1—C2	1.361 (8)	C13—H13B	0.9700
C1—C13	1.513 (7)	C14—C15	1.405 (8)
C2—C3	1.382 (8)	C14—C17	1.492 (8)
C2—H2A	0.9300	C15—C16	1.346 (8)
C3—C4	1.380 (8)	C15—C18	1.517 (8)
C3—H3A	0.9300	C16—C19	1.490 (9)
C4—C5	1.374 (8)	C17—H17A	0.9600
C4—H4A	0.9300	C17—H17B	0.9600
C5—C6	1.515 (7)	C17—H17C	0.9600
C6—H6A	0.9700	C18—H18A	0.9600
C6—H6B	0.9700	C18—H18B	0.9600
C7—C8	1.359 (8)	C18—H18C	0.9600
C7—C10	1.473 (8)	C19—H19A	0.9600
C8—C9	1.417 (8)	C19—H19B	0.9600
C8—C11	1.521 (8)	C19—H19C	0.9600
C9—C12	1.480 (8)
C5—N1—C1	117.1 (5)	C8—C11—H11A	109.5
N3—N2—C7	111.9 (5)	C8—C11—H11B	109.5
N3—N2—C6	118.9 (5)	H11A—C11—H11B	109.5
C7—N2—C6	128.0 (5)	C8—C11—H11C	109.5
C9—N3—N2	105.1 (5)	H11A—C11—H11C	109.5
N5—N4—C16	112.0 (5)	H11B—C11—H11C	109.5
N5—N4—C13	119.1 (5)	C9—C12—H12A	109.5
C16—N4—C13	128.9 (5)	C9—C12—H12B	109.5
C14—N5—N4	104.7 (5)	H12A—C12—H12B	109.5
N1—C1—C2	122.7 (5)	C9—C12—H12C	109.5
N1—C1—C13	113.5 (5)	H12A—C12—H12C	109.5
C2—C1—C13	123.8 (6)	H12B—C12—H12C	109.5
C1—C2—C3	119.9 (6)	N4—C13—C1	115.3 (5)
C1—C2—H2A	120.0	N4—C13—H13A	108.5
C3—C2—H2A	120.0	C1—C13—H13A	108.5
C4—C3—C2	118.1 (6)	N4—C13—H13B	108.5
C4—C3—H3A	121.0	C1—C13—H13B	108.5
C2—C3—H3A	121.0	H13A—C13—H13B	107.5
C5—C4—C3	118.9 (6)	N5—C14—C15	110.9 (5)
C5—C4—H4A	120.5	N5—C14—C17	120.4 (6)
C3—C4—H4A	120.5	C15—C14—C17	128.7 (6)
N1—C5—C4	123.3 (6)	C16—C15—C14	105.3 (5)
N1—C5—C6	114.4 (5)	C16—C15—C18	128.6 (6)
C4—C5—C6	122.3 (5)	C14—C15—C18	126.1 (6)
N2—C6—C5	113.7 (5)	C15—C16—N4	107.1 (5)
N2—C6—H6A	108.8	C15—C16—C19	130.8 (6)
C5—C6—H6A	108.8	N4—C16—C19	122.0 (6)
N2—C6—H6B	108.8	C14—C17—H17A	109.5
C5—C6—H6B	108.8	C14—C17—H17B	109.5
H6A—C6—H6B	107.7	H17A—C17—H17B	109.5
N2—C7—C8	107.3 (5)	C14—C17—H17C	109.5
N2—C7—C10	122.6 (6)	H17A—C17—H17C	109.5
C8—C7—C10	130.1 (6)	H17B—C17—H17C	109.5
C7—C8—C9	105.2 (5)	C15—C18—H18A	109.5
C7—C8—C11	128.7 (6)	C15—C18—H18B	109.5
C9—C8—C11	126.0 (6)	H18A—C18—H18B	109.5
N3—C9—C8	110.5 (5)	C15—C18—H18C	109.5
N3—C9—C12	120.3 (7)	H18A—C18—H18C	109.5
C8—C9—C12	129.1 (6)	H18B—C18—H18C	109.5
C7—C10—H10A	109.5	C16—C19—H19A	109.5
C7—C10—H10B	109.5	C16—C19—H19B	109.5
H10A—C10—H10B	109.5	H19A—C19—H19B	109.5
C7—C10—H10C	109.5	C16—C19—H19C	109.5
H10A—C10—H10C	109.5	H19A—C19—H19C	109.5
H10B—C10—H10C	109.5	H19B—C19—H19C	109.5

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C6—H6a···N5^i	0.97	2.56	3.522 (8)	175
C13—H13a···N3^ii	0.97	2.56	3.526 (8)	173

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