1-[5-(4-Hydr­oxy-3-methoxy­phen­yl)-3-methyl-4,5-dihydro­-1H-pyrazol-1-yl]ethanone

Wang, S.-F.; zhu, W.; Yang, X.; Zhou, L.-J.

doi:10.1107/S160053680503518X

1-[5-(4-Hydroxy-3-methoxyphenyl)-3-methyl-4,5-dihydro-1H-pyrazol-1-yl]ethanone

S.-F. Wang, W. Zhu, X. Yang and L.-J. Zhou

The title compound, C₁₃H₁₆N₂O₃, was synthesized from vanillin, acetone and hydrazine monohydrate. An intermolecular O—H

O hydrogen bond connects the molecules into infinite one-dimensional chains.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S160053680503518X/wn6396sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S160053680503518X/wn6396Isup2.hkl Contains datablock I

CCDC reference: 294024

checkCIF report

Key indicators

Single-crystal X-ray study
T = 293 K
Mean (C-C) = 0.002 Å
R factor = 0.049
wR factor = 0.141
Data-to-parameter ratio = 17.3

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT029_ALERT_3_B _diffrn_measured_fraction_theta_full Low .......       0.95

Alert level C
PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given .......          ?
PLAT199_ALERT_1_C Check the Reported _cell_measurement_temperature        293 K
PLAT200_ALERT_1_C Check the Reported _diffrn_ambient_temperature .        293 K

   0 ALERT level A = In general: serious problem
   1 ALERT level B = Potentially serious problem
   3 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
   0 ALERT type 2 Indicator that the structure model may be wrong or deficient
   1 ALERT type 3 Indicator that the structure quality may be low
   1 ALERT type 4 Improvement, methodology, query or suggestion


checkCIF publication errors

Alert level A
ATOM001_ALERT_1_A  _atom_type_scat_source is missing
            Reference to scattering factors applied.

   1 ALERT level A = Data missing that is essential or data in wrong format
   0 ALERT level G = General alerts. Data that may be required is missing

Computing details top

Data collection: SMART (Bruker, 2002); cell refinement: SAINT (Bruker, 2002); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Sheldrick, 2000); software used to prepare material for publication: SHELXTL.

1-(5-(4-hydroxy-3-methoxyphenyl)-3-methyl-4,5-dihydropyrazol-1-yl)-ethanone top

Crystal data top

C₁₃H₁₆N₂O₃	F(000) = 528
M_r = 248.28	D_x = 1.352 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
a = 7.5862 (6) Å	Cell parameters from 4666 reflections
b = 10.5414 (9) Å	θ = 2.4–27.9°
c = 15.6452 (13) Å	µ = 0.10 mm⁻¹
β = 102.913 (1)°	T = 293 K
V = 1219.49 (17) Å³	Plate, colourless
Z = 4	0.22 × 0.12 × 0.04 mm

Data collection top

Bruker SMART CCD area detector diffractometer	2271 reflections with I > 2σ(I)
Radiation source: fine-focus sealedtube	R_int = 0.061
Graphite monochromator	θ_max = 27.9°, θ_min = 2.4°
φ and ω scans	h = −9→9
10433 measured reflections	k = −13→13
2893 independent reflections	l = −20→19

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)] = 0.050	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.141	H-atom parameters constrained
S = 1.05	w = 1/[σ²(F_o²) + (0.081P)² + 0.0609P] where P = (F_o² + 2F_c²)/3
2893 reflections	(Δ/σ)_max = 0.001
167 parameters	Δρ_max = 0.30 e Å⁻³
0 restraints	Δρ_min = −0.23 e Å⁻³

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
N1	0.68420 (14)	−0.09002 (11)	0.14043 (8)	0.0341 (3)
O1	1.23438 (14)	0.37267 (11)	0.17968 (8)	0.0496 (3)
H1	1.3266	0.3619	0.2179	0.074*
N2	0.50968 (15)	−0.10015 (11)	0.08657 (8)	0.0351 (3)
O3	0.95458 (14)	−0.17535 (11)	0.19561 (9)	0.0548 (3)
C4	1.10610 (17)	0.28676 (13)	0.19044 (10)	0.0339 (3)
O2	0.92813 (16)	0.37700 (11)	0.06366 (8)	0.0513 (3)
C5	1.13115 (18)	0.20335 (13)	0.25949 (9)	0.0345 (3)
H5	1.2377	0.2057	0.3026	0.041*
C1	0.83850 (17)	0.11013 (12)	0.20232 (9)	0.0310 (3)
C6	0.99764 (18)	0.11515 (13)	0.26529 (9)	0.0340 (3)
H6	1.0161	0.0589	0.3123	0.041*
C2	0.81057 (18)	0.19775 (13)	0.13336 (9)	0.0325 (3)
H2	0.7027	0.1965	0.0911	0.039*
C3	0.94242 (19)	0.28625 (13)	0.12762 (9)	0.0339 (3)
C9	0.40911 (18)	−0.02067 (13)	0.11477 (9)	0.0336 (3)
C7	0.69904 (18)	0.00970 (13)	0.20889 (9)	0.0344 (3)
H7	0.7316	−0.0302	0.2669	0.041*
C11	0.81033 (19)	−0.17982 (13)	0.14113 (11)	0.0381 (4)
C8	0.50222 (18)	0.05534 (15)	0.19217 (10)	0.0403 (4)
H8A	0.4507	0.0388	0.2425	0.048*
H8B	0.4938	0.1454	0.1792	0.048*
C12	0.7698 (2)	−0.28377 (16)	0.07422 (13)	0.0541 (5)
H12A	0.8811	−0.3189	0.0654	0.081*
H12B	0.7015	−0.2500	0.0199	0.081*
H12C	0.7009	−0.3490	0.0946	0.081*
C13	0.7644 (3)	0.38608 (17)	0.00018 (12)	0.0578 (5)
H13A	0.7412	0.3074	−0.0312	0.087*
H13B	0.7732	0.4532	−0.0401	0.087*
H13C	0.6674	0.4039	0.0286	0.087*
C10	0.21349 (19)	−0.00653 (17)	0.07377 (11)	0.0475 (4)
H10A	0.1838	−0.0571	0.0215	0.071*
H10B	0.1872	0.0809	0.0592	0.071*
H10C	0.1431	−0.0343	0.1142	0.071*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N1	0.0245 (6)	0.0314 (6)	0.0440 (7)	−0.0016 (4)	0.0026 (5)	−0.0040 (5)
O1	0.0322 (6)	0.0522 (7)	0.0599 (8)	−0.0146 (5)	0.0009 (5)	0.0051 (5)
N2	0.0279 (6)	0.0351 (6)	0.0399 (7)	−0.0011 (5)	0.0024 (5)	−0.0002 (5)
O3	0.0296 (6)	0.0481 (7)	0.0806 (9)	0.0047 (5)	−0.0004 (6)	0.0075 (6)
C4	0.0261 (6)	0.0327 (7)	0.0422 (8)	−0.0035 (5)	0.0063 (6)	−0.0062 (6)
O2	0.0460 (6)	0.0488 (7)	0.0522 (7)	−0.0106 (5)	−0.0033 (5)	0.0158 (5)
C5	0.0240 (6)	0.0397 (8)	0.0362 (8)	−0.0004 (5)	−0.0009 (5)	−0.0077 (6)
C1	0.0250 (6)	0.0325 (7)	0.0349 (8)	−0.0018 (5)	0.0051 (6)	−0.0061 (6)
C6	0.0304 (7)	0.0366 (7)	0.0331 (8)	0.0013 (6)	0.0031 (6)	−0.0016 (6)
C2	0.0243 (6)	0.0356 (7)	0.0346 (7)	−0.0002 (5)	0.0000 (5)	−0.0040 (6)
C3	0.0317 (7)	0.0323 (7)	0.0357 (8)	−0.0001 (5)	0.0036 (6)	−0.0013 (6)
C9	0.0264 (6)	0.0351 (7)	0.0389 (8)	−0.0009 (5)	0.0061 (6)	0.0040 (6)
C7	0.0291 (7)	0.0363 (7)	0.0371 (8)	−0.0032 (5)	0.0063 (6)	−0.0016 (6)
C11	0.0270 (7)	0.0315 (7)	0.0564 (10)	−0.0005 (5)	0.0103 (6)	0.0050 (6)
C8	0.0287 (7)	0.0422 (8)	0.0523 (9)	−0.0050 (6)	0.0141 (6)	−0.0103 (7)
C12	0.0505 (10)	0.0403 (9)	0.0745 (13)	0.0053 (7)	0.0203 (9)	−0.0074 (8)
C13	0.0632 (11)	0.0476 (10)	0.0503 (11)	−0.0067 (8)	−0.0139 (9)	0.0099 (8)
C10	0.0281 (7)	0.0577 (10)	0.0531 (10)	0.0052 (7)	0.0015 (7)	−0.0014 (8)

Geometric parameters (Å, º) top

N1—C11	1.3443 (18)	C2—H2	0.9300
N1—N2	1.4055 (16)	C9—C10	1.4868 (18)
N1—C7	1.4869 (18)	C9—C8	1.492 (2)
O1—C4	1.3670 (16)	C7—C8	1.5345 (18)
O1—H1	0.8200	C7—H7	0.9800
N2—C9	1.2763 (18)	C11—C12	1.499 (2)
O3—C11	1.2285 (18)	C8—H8A	0.9700
C4—C5	1.373 (2)	C8—H8B	0.9700
C4—C3	1.4009 (19)	C12—H12A	0.9600
O2—C3	1.3711 (18)	C12—H12B	0.9600
O2—C13	1.409 (2)	C12—H12C	0.9600
C5—C6	1.3927 (19)	C13—H13A	0.9600
C5—H5	0.9300	C13—H13B	0.9600
C1—C6	1.3782 (19)	C13—H13C	0.9600
C1—C2	1.400 (2)	C10—H10A	0.9600
C1—C7	1.5163 (18)	C10—H10B	0.9600
C6—H6	0.9300	C10—H10C	0.9600
C2—C3	1.3853 (19)

C11—N1—N2	121.66 (12)	N1—C7—H7	109.1
C11—N1—C7	123.55 (12)	C1—C7—H7	109.1
N2—N1—C7	113.27 (10)	C8—C7—H7	109.1
C4—O1—H1	109.5	O3—C11—N1	120.05 (14)
C9—N2—N1	107.38 (12)	O3—C11—C12	121.63 (13)
O1—C4—C5	122.96 (12)	N1—C11—C12	118.33 (14)
O1—C4—C3	117.38 (13)	C9—C8—C7	103.66 (11)
C5—C4—C3	119.66 (12)	C9—C8—H8A	111.0
C3—O2—C13	118.37 (12)	C7—C8—H8A	111.0
C4—C5—C6	120.27 (13)	C9—C8—H8B	111.0
C4—C5—H5	119.9	C7—C8—H8B	111.0
C6—C5—H5	119.9	H8A—C8—H8B	109.0
C6—C1—C2	118.89 (12)	C11—C12—H12A	109.5
C6—C1—C7	119.43 (13)	C11—C12—H12B	109.5
C2—C1—C7	121.68 (12)	H12A—C12—H12B	109.5
C1—C6—C5	120.84 (13)	C11—C12—H12C	109.5
C1—C6—H6	119.6	H12A—C12—H12C	109.5
C5—C6—H6	119.6	H12B—C12—H12C	109.5
C3—C2—C1	120.48 (13)	O2—C13—H13A	109.5
C3—C2—H2	119.8	O2—C13—H13B	109.5
C1—C2—H2	119.8	H13A—C13—H13B	109.5
O2—C3—C2	125.22 (13)	O2—C13—H13C	109.5
O2—C3—C4	114.99 (12)	H13A—C13—H13C	109.5
C2—C3—C4	119.78 (13)	H13B—C13—H13C	109.5
N2—C9—C10	122.19 (14)	C9—C10—H10A	109.5
N2—C9—C8	114.96 (12)	C9—C10—H10B	109.5
C10—C9—C8	122.84 (13)	H10A—C10—H10B	109.5
N1—C7—C1	112.73 (11)	C9—C10—H10C	109.5
N1—C7—C8	100.64 (10)	H10A—C10—H10C	109.5
C1—C7—C8	115.89 (12)	H10B—C10—H10C	109.5

C11—N1—N2—C9	164.29 (13)	N1—N2—C9—C8	0.16 (17)
C7—N1—N2—C9	−2.11 (15)	C11—N1—C7—C1	72.79 (17)
O1—C4—C5—C6	−177.85 (13)	N2—N1—C7—C1	−121.11 (12)
C3—C4—C5—C6	2.6 (2)	C11—N1—C7—C8	−163.13 (13)
C2—C1—C6—C5	−1.8 (2)	N2—N1—C7—C8	2.98 (14)
C7—C1—C6—C5	177.73 (12)	C6—C1—C7—N1	−109.30 (14)
C4—C5—C6—C1	−0.2 (2)	C2—C1—C7—N1	70.21 (16)
C6—C1—C2—C3	1.3 (2)	C6—C1—C7—C8	135.50 (13)
C7—C1—C2—C3	−178.18 (12)	C2—C1—C7—C8	−45.00 (18)
C13—O2—C3—C2	2.9 (2)	N2—N1—C11—O3	−172.01 (13)
C13—O2—C3—C4	−177.34 (14)	C7—N1—C11—O3	−7.0 (2)
C1—C2—C3—O2	−179.16 (13)	N2—N1—C11—C12	8.1 (2)
C1—C2—C3—C4	1.1 (2)	C7—N1—C11—C12	173.06 (13)
O1—C4—C3—O2	−2.42 (19)	N2—C9—C8—C7	1.70 (17)
C5—C4—C3—O2	177.17 (13)	C10—C9—C8—C7	−178.96 (13)
O1—C4—C3—C2	177.39 (13)	N1—C7—C8—C9	−2.58 (14)
C5—C4—C3—C2	−3.0 (2)	C1—C7—C8—C9	119.30 (13)
N1—N2—C9—C10	−179.20 (13)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O3ⁱ	0.82	1.93	2.752 (2)	176

Symmetry code: (i) −x+5/2, y+1/2, −z+1/2.

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1-[5-(4-Hydr­oxy-3-methoxy­phen­yl)-3-methyl-4,5-dihydro­-1H-pyrazol-1-yl]ethanone

Supporting information

Key indicators

checkCIF/PLATON results

1-[5-(4-Hydroxy-3-methoxyphenyl)-3-methyl-4,5-dihydro-1H-pyrazol-1-yl]ethanone