3,5-Dimethyl-1-(2-pyridylcarbon­yl)-5-[(2-pyridylcarbon­yl)hydrazino]-2-pyrazoline methanol hemisolvate

Chen, Y.; Yang, H.; Li, D.; Wang, D.

doi:10.1107/S1600536808027335

organic compounds

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ISSN: 2056-9890

Volume 64| Part 9| September 2008| Page o1842

doi:10.1107/S1600536808027335

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3,5-Dimethyl-1-(2-pyridylcarbonyl)-5-[(2-pyridylcarbonyl)hydrazino]-2-pyrazoline methanol hemisolvate

Yuting Chen,^a,^b Hua Yang,^b Dacheng Li ^b ^* and Daqi Wang ^b

^aDepartment of Chemistry, Dezhou University, Dezhou 253023, People's Republic of China, and ^bCollege of Chemistry and Chemical Engineering, Liaocheng University, Liaocheng 252059, People's Republic of China
^*Correspondence e-mail: lidacheng@lcu.edu.cn

(Received 11 August 2008; accepted 25 August 2008; online 30 August 2008)

The title compound, C₁₇H₁₈N₆O₂·0.5CH₃OH, exists in the double keto form and adopts a highly puckered geometry, stabilized by intramolecular N—H⋯O and N—H⋯N hydrogen bonds. Intermolecular N—H⋯N hydrogen bonds and π–π stacking interactions [centroid–centroid separation = 3.654 (1) Å] assemble the molecules into chains running in the [111] direction. The methanol solvent molecule is disordered over two sites related by inversion and forms a bifurcated O—H⋯(N,O) hydrogen bond.

Related literature

Two manganese metallocrowns with N-acyl-3-hydroxy-2-naphthalenecarbohydrazide ligands were synthesized by Dou et al. (2006 ). The 1-benzoyl-3,5-dimethyl-5-(1-benzoylhydrazido)pyrazoline ligand and two pyrazolone derivatives were synthesized by Liu et al. (2004 ) and Mukhopadhyay & Pal (2004 ).

Experimental

Crystal data

C₁₇H₁₈N₆O₂·0.5CH₄O
M_r = 354.40
Triclinic, $[P \overline 1]$
a = 9.0111 (12) Å
b = 10.6406 (17) Å
c = 10.814 (2) Å
α = 78.221 (1)°
β = 66.414 (1)°
γ = 86.477 (2)°
V = 930.0 (2) Å³
Z = 2
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 298 (2) K
0.53 × 0.48 × 0.46 mm

Data collection

Bruker SMART1000 CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.955, T_max = 0.960
4781 measured reflections
3189 independent reflections
2189 reflections with I > 2σ(I)
R_int = 0.023

Refinement

R[F² > 2σ(F²)] = 0.065
wR(F²) = 0.216
S = 1.00
3189 reflections
245 parameters
H-atom parameters constrained
Δρ_max = 0.84 e Å⁻³
Δρ_min = −0.20 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N3—H3⋯N6	0.88	2.30	2.667 (3)	105
N3—H3⋯N4ⁱ	0.88	2.50	3.136 (3)	130
N4—H4⋯O1	0.88	2.59	3.167 (3)	124
N4—H4⋯O2	0.88	2.33	2.727 (3)	108
O3—H3A⋯O2	0.82	2.56	2.932 (9)	109
O3—H3A⋯N4	0.82	2.62	3.361 (9)	151
Symmetry code: (i) -x+1, -y+1, -z.

Data collection: SMART (Siemens, 1996 ); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808027335/hb2780sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808027335/hb2780Isup2.hkl

checkCIF report

Comment top

After assembling successfully two azametallacrowns based on N-acyl-3-hydroxy-2-naphthalenecarbohydrazide (Dou et al., 2006), and as an extension of our work on the structures of aroylhydrazine derivatives, the title compound, (I), was synthesized and characterized.

In compound (I), the C6—O1 and C12—O2 distances are 1.225 (3) Å, 1.227 (3)Å respectively, indicating that the molecule of (I) exists in the double keto form (Liu et al., 2004), and the distances of N(1)—N(2), C(3)—N(1) and C(1)—N(2) are 1.399 (3) Å, 1.492 (3)Å and 1.266 (3)Å (Table 1), which are in agreement with these of analogous compounds (Mukhopadhyay & Pal, 2004). The title molecule is chiral: in the arbitrarily chosen asymmetric unit, C3 has R configuration, but crystal symmetry generates a racemic mixture.

The three rings in (I), 2-picoloyl ring (A), pyrazoline ring (B) and 2-picoloylhydrazido ring (C), make dihedral angles of 65.5 (2)(A/B), 56.4 (1)(B/C) and 95.5 (1)° (A/C) respectively, showing the whole molecule exhibits highly puckered geometry.

There is intramolecular N4—H4···O1 hydrogen bond, which further stabilizes the molecular configuration (Fig. 1, Table 1), whereas double intermolecular N3—H3···N4 hydrogen bonds link molecules into centrosymmetric dimers. The dimers are assembled into chains along [111] through intermolecular π–π interactions between pyridine rings with a centrosymmetric-centrosymmetric distance of 3.654 (1)Å [Cg is a centroid of N6/C13—C17; symmetry code: (ii) -x, 1 - y, 1 - z] (Fig. 2).

Related literature top

Two manganese metallacrowns with N-acyl-3-hydroxy- 2-naphthalenecarbohydrazide ligand were synthesized by Dou et al. (2006). The 1-benzoyl-3,5-dimethyl-5-(1-benzoylhydrazido)pyrazoline ligand and two pyrazolone derivatives were synthesized by Liu et al. (2004) and Mukhopadhyay & Pal (2004).

Experimental top

2-Picoloylhydrazine (0.548 g, 4 mmol) and ice acetic acid (0.48 g, 8 mmol) were added to a mixture of methanol/glycol (25 ml, 3:2), then 0.21 ml of acetylacetone (0.205 g, 2.05 mmol) was added and reacted for 3 h at 323–333 K. The solution was cooled to room temperature. After the solution was allowed to stand for three weeks, colourless blocks of (I) were obtained. When recrystallised from pure methanol, the same compound arises. Yield: 0.591 g, 81.5%. m.p.: 585–587 K. Anal. for C_17.5H₂₀N₆O_2.5: Calc. C, 59.25; H, 5.64; N, 23.70; Found: C, 59.21; H, 5.48; N, 23.38%.

Computing details top

Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT (Siemens, 1996); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structure of (I). Displacement ellipsoids for the non-hydrogen atoms are drawn at the 30% probability level.
	Fig. 2. Crystal packing of (I); symmetry code: (i) 1 - x, 1 - y, -z; (ii) -x, 1 - y, 1 - z.

3,5-Dimethyl-1-(2-pyridylcarbonyl)-5-[(2-pyridylcarbonyl)hydrazino]-2- pyrazoline methanol hemisolvate top

Crystal data top

C₁₇H₁₈N₆O₂·0.5CH₄O	Z = 2
M_r = 354.40	F(000) = 374
Triclinic, P1	D_x = 1.266 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 9.0111 (12) Å	Cell parameters from 1800 reflections
b = 10.6406 (17) Å	θ = 2.5–24.8°
c = 10.814 (2) Å	µ = 0.09 mm⁻¹
α = 78.221 (1)°	T = 298 K
β = 66.414 (1)°	Block, colourless
γ = 86.477 (2)°	0.53 × 0.48 × 0.46 mm
V = 930.0 (2) Å³

Data collection top

Bruker SMART1000 CCD diffractometer	3189 independent reflections
Radiation source: fine-focus sealed tube	2189 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.023
ω scans	θ_max = 25.0°, θ_min = 2.5°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −10→10
T_min = 0.955, T_max = 0.960	k = −12→7
4781 measured reflections	l = −12→12

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.065	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.216	H-atom parameters constrained
S = 1.00	w = 1/[σ²(F_o²) + (0.139P)² + 0.2337P] where P = (F_o² + 2F_c²)/3
3189 reflections	(Δ/σ)_max = 0.001
245 parameters	Δρ_max = 0.84 e Å⁻³
0 restraints	Δρ_min = −0.20 e Å⁻³

Crystal data top

C₁₇H₁₈N₆O₂·0.5CH₄O	γ = 86.477 (2)°
M_r = 354.40	V = 930.0 (2) Å³
Triclinic, P1	Z = 2
a = 9.0111 (12) Å	Mo Kα radiation
b = 10.6406 (17) Å	µ = 0.09 mm⁻¹
c = 10.814 (2) Å	T = 298 K
α = 78.221 (1)°	0.53 × 0.48 × 0.46 mm
β = 66.414 (1)°

Data collection top

Bruker SMART1000 CCD diffractometer	3189 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	2189 reflections with I > 2σ(I)
T_min = 0.955, T_max = 0.960	R_int = 0.023
4781 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.065	0 restraints
wR(F²) = 0.216	H-atom parameters constrained
S = 1.00	Δρ_max = 0.84 e Å⁻³
3189 reflections	Δρ_min = −0.20 e Å⁻³
245 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.

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 (Å²) top

	x	y	z	U_iso*/U_eq	Occ. (<1)
N1	0.4874 (3)	0.8072 (2)	0.1320 (2)	0.0433 (6)
N2	0.3319 (3)	0.8492 (2)	0.1473 (2)	0.0466 (6)
N3	0.4382 (3)	0.5456 (2)	0.1581 (2)	0.0433 (6)
H3	0.3688	0.5191	0.1298	0.052*
N4	0.5844 (3)	0.6043 (2)	0.0554 (2)	0.0430 (6)
H4	0.6572	0.6046	0.0905	0.052*
N5	0.4085 (4)	0.9947 (2)	0.3280 (3)	0.0636 (8)
N6	0.1726 (3)	0.4050 (2)	0.3258 (2)	0.0508 (6)
O1	0.6856 (3)	0.7836 (2)	0.2105 (2)	0.0618 (6)
O2	0.5370 (3)	0.5115 (2)	0.3232 (2)	0.0665 (7)
O3	0.8469 (9)	0.4142 (7)	0.1517 (8)	0.123 (2)	0.50
H3A	0.7709	0.4329	0.1284	0.185*	0.50
C1	0.3048 (3)	0.8290 (3)	0.0467 (3)	0.0457 (7)
C2	0.4392 (4)	0.7663 (3)	−0.0514 (3)	0.0493 (7)
H2A	0.4832	0.8217	−0.1416	0.059*
H2B	0.4026	0.6859	−0.0599	0.059*
C3	0.5665 (3)	0.7430 (2)	0.0119 (3)	0.0425 (6)
C4	0.1544 (4)	0.8701 (4)	0.0264 (4)	0.0692 (9)
H4A	0.0845	0.9090	0.1013	0.104*
H4B	0.1001	0.7967	0.0232	0.104*
H4C	0.1813	0.9311	−0.0586	0.104*
C5	0.7302 (4)	0.8002 (3)	−0.0844 (3)	0.0545 (8)
H5A	0.7209	0.8906	−0.1139	0.082*
H5B	0.7718	0.7598	−0.1631	0.082*
H5C	0.8027	0.7866	−0.0379	0.082*
C6	0.5483 (3)	0.8179 (3)	0.2250 (3)	0.0441 (7)
C7	0.4413 (3)	0.8700 (3)	0.3491 (3)	0.0461 (7)
C8	0.3925 (4)	0.7926 (3)	0.4769 (3)	0.0554 (8)
H8	0.4203	0.7066	0.4874	0.066*
C9	0.3014 (5)	0.8454 (4)	0.5893 (3)	0.0711 (10)
H9	0.2640	0.7951	0.6774	0.085*
C10	0.2671 (5)	0.9717 (4)	0.5696 (4)	0.0780 (11)
H10	0.2066	1.0094	0.6444	0.094*
C11	0.3214 (5)	1.0429 (4)	0.4402 (4)	0.0750 (10)
H11	0.2969	1.1295	0.4287	0.090*
C12	0.4278 (3)	0.4976 (2)	0.2862 (3)	0.0423 (6)
C13	0.2742 (3)	0.4273 (2)	0.3813 (3)	0.0407 (6)
C14	0.2423 (4)	0.3888 (3)	0.5204 (3)	0.0510 (7)
H14	0.3164	0.4058	0.5552	0.061*
C15	0.0991 (4)	0.3252 (3)	0.6047 (3)	0.0587 (8)
H15	0.0736	0.2988	0.6985	0.070*
C16	−0.0062 (4)	0.3010 (3)	0.5495 (3)	0.0639 (9)
H16	−0.1035	0.2567	0.6048	0.077*
C17	0.0339 (4)	0.3432 (3)	0.4113 (3)	0.0618 (8)
H17	−0.0397	0.3278	0.3752	0.074*
C20	0.9726 (6)	0.5000 (5)	0.0745 (5)	0.0401 (12)	0.50
H20A	1.0622	0.4779	0.1024	0.048*	0.50
H20B	0.9384	0.5854	0.0911	0.048*	0.50
H20C	1.0000	0.5000	0.0000	0.048*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N1	0.0482 (13)	0.0436 (13)	0.0418 (12)	0.0024 (10)	−0.0199 (10)	−0.0125 (10)
N2	0.0497 (14)	0.0456 (13)	0.0477 (13)	0.0048 (10)	−0.0211 (11)	−0.0134 (10)
N3	0.0463 (13)	0.0437 (13)	0.0415 (12)	−0.0045 (10)	−0.0194 (10)	−0.0062 (10)
N4	0.0471 (13)	0.0415 (13)	0.0398 (12)	−0.0012 (10)	−0.0173 (10)	−0.0064 (9)
N5	0.090 (2)	0.0486 (15)	0.0555 (15)	0.0058 (13)	−0.0304 (15)	−0.0154 (12)
N6	0.0494 (14)	0.0605 (15)	0.0429 (13)	−0.0054 (11)	−0.0184 (11)	−0.0088 (11)
O1	0.0585 (14)	0.0762 (15)	0.0609 (13)	0.0051 (11)	−0.0320 (11)	−0.0193 (11)
O2	0.0690 (14)	0.0827 (16)	0.0538 (12)	−0.0232 (12)	−0.0345 (11)	0.0024 (11)
O3	0.113 (5)	0.134 (6)	0.111 (5)	−0.005 (4)	−0.041 (4)	−0.007 (4)
C1	0.0533 (16)	0.0413 (15)	0.0450 (15)	0.0001 (12)	−0.0241 (13)	−0.0042 (12)
C2	0.0630 (18)	0.0496 (16)	0.0419 (15)	0.0019 (13)	−0.0281 (14)	−0.0079 (12)
C3	0.0530 (16)	0.0407 (15)	0.0357 (13)	0.0007 (12)	−0.0186 (12)	−0.0094 (11)
C4	0.065 (2)	0.077 (2)	0.074 (2)	0.0058 (17)	−0.0385 (19)	−0.0120 (18)
C5	0.0588 (18)	0.0510 (17)	0.0454 (16)	−0.0047 (14)	−0.0119 (14)	−0.0077 (13)
C6	0.0533 (17)	0.0404 (15)	0.0443 (15)	−0.0027 (12)	−0.0254 (13)	−0.0069 (12)
C7	0.0574 (17)	0.0432 (16)	0.0478 (16)	−0.0011 (12)	−0.0292 (14)	−0.0125 (12)
C8	0.0680 (19)	0.0529 (17)	0.0497 (17)	−0.0040 (14)	−0.0277 (15)	−0.0092 (14)
C9	0.084 (2)	0.080 (3)	0.0473 (18)	−0.0121 (19)	−0.0231 (18)	−0.0111 (17)
C10	0.093 (3)	0.084 (3)	0.059 (2)	0.007 (2)	−0.024 (2)	−0.036 (2)
C11	0.100 (3)	0.061 (2)	0.067 (2)	0.0109 (19)	−0.030 (2)	−0.0286 (18)
C12	0.0486 (15)	0.0418 (15)	0.0406 (14)	0.0003 (11)	−0.0209 (13)	−0.0101 (12)
C13	0.0461 (15)	0.0403 (14)	0.0384 (14)	0.0033 (11)	−0.0183 (12)	−0.0108 (11)
C14	0.0580 (18)	0.0562 (18)	0.0411 (15)	0.0010 (14)	−0.0223 (14)	−0.0089 (13)
C15	0.0604 (19)	0.066 (2)	0.0420 (16)	−0.0015 (15)	−0.0142 (15)	−0.0052 (14)
C16	0.0520 (18)	0.074 (2)	0.0525 (18)	−0.0037 (15)	−0.0081 (15)	−0.0099 (16)
C17	0.0517 (18)	0.078 (2)	0.0546 (18)	−0.0080 (15)	−0.0206 (16)	−0.0092 (16)
C20	0.025 (2)	0.060 (3)	0.033 (2)	0.003 (2)	−0.015 (2)	0.001 (2)

Geometric parameters (Å, º) top

N1—C6	1.350 (3)	C4—H4C	0.9600
N1—N2	1.399 (3)	C5—H5A	0.9600
N1—C3	1.492 (3)	C5—H5B	0.9600
N2—C1	1.266 (3)	C5—H5C	0.9600
N3—C12	1.343 (3)	C6—C7	1.497 (4)
N3—N4	1.417 (3)	C7—C8	1.369 (4)
N3—H3	0.8800	C8—C9	1.375 (5)
N4—C3	1.473 (3)	C8—H8	0.9300
N4—H4	0.8802	C9—C10	1.354 (5)
N5—C7	1.336 (4)	C9—H9	0.9300
N5—C11	1.339 (4)	C10—C11	1.355 (5)
N6—C17	1.333 (4)	C10—H10	0.9300
N6—C13	1.334 (3)	C11—H11	0.9300
O1—C6	1.225 (3)	C12—C13	1.486 (4)
O2—C12	1.227 (3)	C13—C14	1.388 (4)
O3—C20	1.368 (9)	C14—C15	1.367 (4)
O3—H3A	0.8200	C14—H14	0.9300
C1—C2	1.483 (4)	C15—C16	1.367 (5)
C1—C4	1.484 (4)	C15—H15	0.9300
C2—C3	1.539 (4)	C16—C17	1.371 (5)
C2—H2A	0.9700	C16—H16	0.9300
C2—H2B	0.9700	C17—H17	0.9300
C3—C5	1.501 (4)	C20—H20A	0.9700
C4—H4A	0.9600	C20—H20B	0.9700
C4—H4B	0.9600	C20—H20C	0.7426

C6—N1—N2	121.2 (2)	O1—C6—C7	120.7 (2)
C6—N1—C3	125.9 (2)	N1—C6—C7	118.0 (2)
N2—N1—C3	112.7 (2)	N5—C7—C8	123.5 (3)
C1—N2—N1	108.6 (2)	N5—C7—C6	116.5 (2)
C12—N3—N4	120.4 (2)	C8—C7—C6	119.7 (3)
C12—N3—H3	119.6	C7—C8—C9	118.2 (3)
N4—N3—H3	117.0	C7—C8—H8	120.9
N3—N4—C3	111.8 (2)	C9—C8—H8	120.9
N3—N4—H4	110.0	C10—C9—C8	118.9 (3)
C3—N4—H4	101.3	C10—C9—H9	120.5
C7—N5—C11	116.4 (3)	C8—C9—H9	120.5
C17—N6—C13	116.6 (2)	C9—C10—C11	119.5 (3)
C20—O3—H3A	109.5	C9—C10—H10	120.2
N2—C1—C2	114.1 (2)	C11—C10—H10	120.2
N2—C1—C4	122.5 (3)	N5—C11—C10	123.4 (3)
C2—C1—C4	123.3 (3)	N5—C11—H11	118.3
C1—C2—C3	104.4 (2)	C10—C11—H11	118.3
C1—C2—H2A	110.9	O2—C12—N3	122.5 (3)
C3—C2—H2A	110.9	O2—C12—C13	122.0 (2)
C1—C2—H2B	110.9	N3—C12—C13	115.5 (2)
C3—C2—H2B	110.9	N6—C13—C14	123.4 (3)
H2A—C2—H2B	108.9	N6—C13—C12	116.6 (2)
N4—C3—N1	111.9 (2)	C14—C13—C12	120.1 (2)
N4—C3—C5	108.3 (2)	C15—C14—C13	118.3 (3)
N1—C3—C5	113.0 (2)	C15—C14—H14	120.9
N4—C3—C2	110.5 (2)	C13—C14—H14	120.9
N1—C3—C2	99.8 (2)	C14—C15—C16	119.1 (3)
C5—C3—C2	113.2 (2)	C14—C15—H15	120.4
C1—C4—H4A	109.5	C16—C15—H15	120.4
C1—C4—H4B	109.5	C15—C16—C17	119.0 (3)
H4A—C4—H4B	109.5	C15—C16—H16	120.5
C1—C4—H4C	109.5	C17—C16—H16	120.5
H4A—C4—H4C	109.5	N6—C17—C16	123.6 (3)
H4B—C4—H4C	109.5	N6—C17—H17	118.2
C3—C5—H5A	109.5	C16—C17—H17	118.2
C3—C5—H5B	109.5	O3—C20—H20A	109.4
H5A—C5—H5B	109.5	O3—C20—H20B	109.4
C3—C5—H5C	109.5	H20A—C20—H20B	108.0
H5A—C5—H5C	109.5	O3—C20—H20C	111.3
H5B—C5—H5C	109.5	H20A—C20—H20C	109.4
O1—C6—N1	121.3 (3)	H20B—C20—H20C	109.4

C6—N1—N2—C1	179.7 (2)	O1—C6—C7—N5	111.1 (3)
C3—N1—N2—C1	−4.8 (3)	N1—C6—C7—N5	−70.4 (3)
C12—N3—N4—C3	−113.3 (3)	O1—C6—C7—C8	−64.1 (4)
N1—N2—C1—C2	1.4 (3)	N1—C6—C7—C8	114.4 (3)
N1—N2—C1—C4	−176.0 (3)	N5—C7—C8—C9	1.7 (5)
N2—C1—C2—C3	2.2 (3)	C6—C7—C8—C9	176.6 (3)
C4—C1—C2—C3	179.6 (3)	C7—C8—C9—C10	−1.6 (5)
N3—N4—C3—N1	48.5 (3)	C8—C9—C10—C11	0.7 (6)
N3—N4—C3—C5	173.7 (2)	C7—N5—C11—C10	−0.2 (6)
N3—N4—C3—C2	−61.7 (3)	C9—C10—C11—N5	0.2 (6)
C6—N1—C3—N4	64.0 (3)	N4—N3—C12—O2	6.3 (4)
N2—N1—C3—N4	−111.2 (2)	N4—N3—C12—C13	−174.3 (2)
C6—N1—C3—C5	−58.5 (3)	C17—N6—C13—C14	0.4 (4)
N2—N1—C3—C5	126.3 (2)	C17—N6—C13—C12	−179.3 (3)
C6—N1—C3—C2	−179.0 (2)	O2—C12—C13—N6	−172.3 (3)
N2—N1—C3—C2	5.7 (3)	N3—C12—C13—N6	8.3 (4)
C1—C2—C3—N4	113.4 (2)	O2—C12—C13—C14	8.0 (4)
C1—C2—C3—N1	−4.5 (3)	N3—C12—C13—C14	−171.4 (2)
C1—C2—C3—C5	−124.8 (2)	N6—C13—C14—C15	−0.2 (4)
N2—N1—C6—O1	−178.5 (2)	C12—C13—C14—C15	179.5 (3)
C3—N1—C6—O1	6.6 (4)	C13—C14—C15—C16	0.5 (5)
N2—N1—C6—C7	3.0 (4)	C14—C15—C16—C17	−1.1 (5)
C3—N1—C6—C7	−171.8 (2)	C13—N6—C17—C16	−1.0 (5)
C11—N5—C7—C8	−0.8 (5)	C15—C16—C17—N6	1.3 (5)
C11—N5—C7—C6	−175.8 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3···N6	0.88	2.30	2.667 (3)	105
N3—H3···N4ⁱ	0.88	2.50	3.136 (3)	130
N4—H4···O1	0.88	2.59	3.167 (3)	124
N4—H4···O2	0.88	2.33	2.727 (3)	108
O3—H3A···O2	0.82	2.56	2.932 (9)	109
O3—H3A···N4	0.82	2.62	3.361 (9)	151

Symmetry code: (i) −x+1, −y+1, −z.

Experimental details

Crystal data
Chemical formula	C₁₇H₁₈N₆O₂·0.5CH₄O
M_r	354.40
Crystal system, space group	Triclinic, P1
Temperature (K)	298
a, b, c (Å)	9.0111 (12), 10.6406 (17), 10.814 (2)
α, β, γ (°)	78.221 (1), 66.414 (1), 86.477 (2)
V (Å³)	930.0 (2)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.53 × 0.48 × 0.46

Data collection
Diffractometer	Bruker SMART1000 CCD diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.955, 0.960
No. of measured, independent and observed [I > 2σ(I)] reflections	4781, 3189, 2189
R_int	0.023
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.065, 0.216, 1.00
No. of reflections	3189
No. of parameters	245
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.84, −0.20

Computer programs: SMART (Siemens, 1996), SAINT (Siemens, 1996), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3···N6	0.88	2.30	2.667 (3)	105
N3—H3···N4ⁱ	0.88	2.50	3.136 (3)	130
N4—H4···O1	0.88	2.59	3.167 (3)	124
N4—H4···O2	0.88	2.33	2.727 (3)	108
O3—H3A···O2	0.82	2.56	2.932 (9)	109
O3—H3A···N4	0.82	2.62	3.361 (9)	151

Symmetry code: (i) −x+1, −y+1, −z.

Acknowledgements

The authors acknowledge the support of the National Natural Science Foundation of China (20671048).

References

Dou, J. M., Liu, M. L., Li, D. C. & Wang, D. Q. (2006). Eur. J. Inorg. Chem. 23, 4866–4871. Web of Science CSD CrossRef Google Scholar
Liu, L., Jia, D. Z. & Yu, K. B. (2004). Chin. J. Struct. Chem. 23, 112–118. CAS Google Scholar
Mukhopadhyay, A. & Pal, S. (2004). Polyhedron, 23, 1997–2004. Web of Science CSD CrossRef CAS Google Scholar
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Siemens (1996). SMART and SAINT. Siemens Analytical X-ray Instruments Inc., Madison, Wisconsin, USA. Google Scholar

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

3,5-Di­methyl-1-(2-pyridylcarbon­yl)-5-[(2-pyridylcarbon­yl)hydrazino]-2-pyrazoline methanol hemisolvate

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

3,5-Dimethyl-1-(2-pyridylcarbonyl)-5-[(2-pyridylcarbonyl)hydrazino]-2-pyrazoline methanol hemisolvate