Buy article online - an online subscription or single-article purchase is required to access this article.
Download citation
Download citation
link to html
In the title compound, C16H12ClN3O2, the pyrazole ring makes dihedral angles of 4.6 (1) and 67.1 (1)° with the phenyl and pyridine rings, respectively. The structure displays O—H...N hydrogen bonding.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807030954/hg2243sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536807030954/hg2243Isup2.hkl
Contains datablock I

CCDC reference: 655065

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.004 Å
  • R factor = 0.044
  • wR factor = 0.095
  • Data-to-parameter ratio = 16.4

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ?
Alert level G REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is correct. If it is not, please give the correct count in the _publ_section_exptl_refinement section of the submitted CIF. From the CIF: _diffrn_reflns_theta_max 27.49 From the CIF: _reflns_number_total 3276 Count of symmetry unique reflns 1834 Completeness (_total/calc) 178.63% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 1442 Fraction of Friedel pairs measured 0.786 Are heavy atom types Z>Si present yes PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature 293 K PLAT200_ALERT_1_G Check the Reported _diffrn_ambient_temperature . 293 K PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints ....... 1
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 1 ALERT level C = Check and explain 4 ALERT level G = General alerts; check 3 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 0 ALERT type 5 Informative message, check

Comment top

Pyrazole framework plays an essential role in biologically active compounds. Many pyrazole derivatives are known to exhibit a wide range of biological properties such as anticoagulant (Jia et al., 2004), antipyretic, antibacterial, hypoglycaemic, antihyperglycaemic, analgesic, anti-inflammatory, sedative-hypnotic (Cottineau et al., 2002; Finn et al., 2003), and antitumour (Wei et al., 2006) activities. We report here the crystal structure of the title compound, (I).

Related literature top

For related literature, see: Cottineau et al. (2002); Finn et al. (2003); Jia et al. (2004); Wei et al. (2006); Xia et al. (2007).

Experimental top

A mixture of ethyl 1-((6-chloropyridin-3-yl)methyl)-3-phenyl-1H-pyrazole-5-carboxylate (0.01 mol) that was synthesized according to the literature procedure (Xia et al., 2007) and potassium hydroxide (0.02 mol) in ethanol (40 ml) was heated to reflux for 1 h. The solvent was removed under reduced pressure and the residue was dissolved in water and acidified with hydrochloric acid (10%). The precipitate was filtered and dried to give a white solid (yield 86%). Crystals of (I) suitable for X-ray diffraction were obtained by slow evaporation of a solution of the solid in acetone at room temperature for 6 d.

Refinement top

All H atoms were placed at geometrically calculated positions and allowed to ride with C—H = 0.97 Å (for CH2 groups), and O—H = 0.82 Å; their isotropic displacement parameters were set to 1.2 times (CH2 groups) or 1.5 times (O—H groups) the equivalent displacement parameter of their parent atoms.

Structure description top

Pyrazole framework plays an essential role in biologically active compounds. Many pyrazole derivatives are known to exhibit a wide range of biological properties such as anticoagulant (Jia et al., 2004), antipyretic, antibacterial, hypoglycaemic, antihyperglycaemic, analgesic, anti-inflammatory, sedative-hypnotic (Cottineau et al., 2002; Finn et al., 2003), and antitumour (Wei et al., 2006) activities. We report here the crystal structure of the title compound, (I).

For related literature, see: Cottineau et al. (2002); Finn et al. (2003); Jia et al. (2004); Wei et al. (2006); Xia et al. (2007).

Computing details top

Data collection: APEX2 (Bruker, 2005); cell refinement: APEX2; data reduction: APEX2; program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).

Figures top
[Figure 1] Fig. 1. The molecular strure of (I), showing displacement ellipsoids drawn at 50% probability level.
[Figure 2] Fig. 2. Packing view of (I), shown down the c axis. Hydrogen bonds leading to columns units are drawn as dashed lines.
1-(6-Chloropyridin-3-ylmethyl)-3-phenyl-1H-pyrazole-5-carboxylic acid top
Crystal data top
C16H12ClN3O2F(000) = 2592
Mr = 313.74Dx = 1.454 Mg m3
Orthorhombic, Fdd2Mo Kα radiation, λ = 0.71073 Å
Hall symbol: F 2 -2dCell parameters from 1585 reflections
a = 20.5430 (5) Åθ = 2.5–21.4°
b = 54.5902 (15) ŵ = 0.28 mm1
c = 5.1134 (1) ÅT = 293 K
V = 5734.4 (2) Å3Plate, colourless
Z = 160.26 × 0.14 × 0.04 mm
Data collection top
Bruker APEX2 CCD area-detector
diffractometer
3276 independent reflections
Radiation source: fine-focus sealed tube2193 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.058
φ and ω scansθmax = 27.5°, θmin = 2.5°
Absorption correction: multi-scan
(APEX2; Bruker, 2005)
h = 2526
Tmin = 0.931, Tmax = 0.989k = 6770
11476 measured reflectionsl = 66
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.044H-atom parameters constrained
wR(F2) = 0.095 w = 1/[σ2(Fo2) + (0.0367P)2 + 0.3657P]
where P = (Fo2 + 2Fc2)/3
S = 1.02(Δ/σ)max = 0.001
3276 reflectionsΔρmax = 0.20 e Å3
200 parametersΔρmin = 0.16 e Å3
1 restraintAbsolute structure: Flack (1983), with how many Friedel pairs?
Primary atom site location: structure-invariant direct methodsAbsolute structure parameter: 0.05 (7)
Crystal data top
C16H12ClN3O2V = 5734.4 (2) Å3
Mr = 313.74Z = 16
Orthorhombic, Fdd2Mo Kα radiation
a = 20.5430 (5) ŵ = 0.28 mm1
b = 54.5902 (15) ÅT = 293 K
c = 5.1134 (1) Å0.26 × 0.14 × 0.04 mm
Data collection top
Bruker APEX2 CCD area-detector
diffractometer
3276 independent reflections
Absorption correction: multi-scan
(APEX2; Bruker, 2005)
2193 reflections with I > 2σ(I)
Tmin = 0.931, Tmax = 0.989Rint = 0.058
11476 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.044H-atom parameters constrained
wR(F2) = 0.095Δρmax = 0.20 e Å3
S = 1.02Δρmin = 0.16 e Å3
3276 reflectionsAbsolute structure: Flack (1983), with how many Friedel pairs?
200 parametersAbsolute structure parameter: 0.05 (7)
1 restraint
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
xyzUiso*/Ueq
C10.59781 (18)0.25213 (5)0.3934 (7)0.0630 (9)
H10.59090.26430.51780.076*
C20.65305 (18)0.25237 (6)0.2456 (7)0.0635 (9)
H20.68400.26460.27080.076*
C30.66326 (15)0.23443 (5)0.0576 (6)0.0544 (8)
H30.70090.23480.04370.065*
C40.61805 (12)0.21602 (5)0.0195 (5)0.0383 (6)
C50.56229 (13)0.21617 (5)0.1724 (6)0.0500 (7)
H50.53100.20400.14890.060*
C60.55259 (15)0.23404 (6)0.3588 (6)0.0618 (9)
H60.51520.23380.46120.074*
C70.62922 (12)0.19686 (4)0.1782 (5)0.0348 (6)
C80.67929 (11)0.19464 (4)0.3623 (5)0.0367 (6)
H80.71420.20520.38620.044*
C90.66637 (11)0.17366 (4)0.5004 (5)0.0332 (6)
C100.70235 (12)0.16293 (5)0.7217 (5)0.0359 (6)
C110.57428 (11)0.14209 (4)0.4677 (6)0.0380 (6)
H11A0.52810.14500.44220.046*
H11B0.58110.13860.65170.046*
C120.59414 (11)0.11997 (4)0.3095 (5)0.0350 (6)
C130.64818 (12)0.10619 (4)0.3792 (6)0.0416 (7)
H130.67300.11060.52380.050*
C140.66494 (13)0.08599 (5)0.2343 (6)0.0467 (7)
H140.70120.07660.27690.056*
C150.55921 (11)0.11244 (4)0.0930 (5)0.0377 (6)
H150.52320.12160.04310.045*
C160.62635 (13)0.08010 (5)0.0246 (5)0.0421 (7)
Cl10.64398 (4)0.054295 (13)0.16079 (18)0.0733 (3)
N10.58700 (9)0.17805 (4)0.2025 (4)0.0373 (5)
N20.60997 (9)0.16434 (3)0.3997 (4)0.0357 (5)
N30.57445 (10)0.09264 (4)0.0486 (4)0.0415 (6)
O10.75219 (8)0.17705 (3)0.7891 (4)0.0445 (5)
H1A0.77170.17080.91170.067*
O20.69003 (8)0.14364 (3)0.8283 (4)0.0480 (5)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.091 (2)0.0468 (17)0.051 (2)0.0154 (17)0.009 (2)0.0181 (18)
C20.088 (2)0.0406 (16)0.062 (2)0.0096 (16)0.008 (2)0.0083 (16)
C30.0670 (19)0.0435 (16)0.053 (2)0.0087 (15)0.0061 (15)0.0055 (15)
C40.0491 (16)0.0328 (13)0.0330 (15)0.0067 (12)0.0070 (13)0.0013 (12)
C50.0477 (16)0.0501 (16)0.0523 (19)0.0053 (13)0.0031 (15)0.0144 (16)
C60.0642 (19)0.067 (2)0.054 (2)0.0120 (17)0.0065 (16)0.0159 (19)
C70.0401 (14)0.0307 (13)0.0337 (16)0.0017 (11)0.0022 (12)0.0031 (11)
C80.0392 (14)0.0322 (13)0.0386 (17)0.0012 (10)0.0008 (13)0.0034 (13)
C90.0344 (13)0.0351 (13)0.0300 (14)0.0031 (11)0.0007 (11)0.0010 (12)
C100.0338 (14)0.0411 (15)0.0327 (14)0.0051 (12)0.0011 (11)0.0048 (13)
C110.0324 (13)0.0408 (15)0.0409 (16)0.0010 (11)0.0017 (12)0.0065 (13)
C120.0323 (12)0.0349 (13)0.0379 (15)0.0066 (11)0.0018 (12)0.0110 (13)
C130.0380 (14)0.0449 (15)0.0420 (18)0.0028 (12)0.0123 (13)0.0027 (14)
C140.0486 (16)0.0434 (15)0.0481 (18)0.0103 (13)0.0116 (15)0.0010 (14)
C150.0334 (13)0.0412 (14)0.0386 (16)0.0004 (11)0.0016 (13)0.0139 (14)
C160.0533 (17)0.0368 (14)0.0361 (17)0.0018 (13)0.0048 (13)0.0031 (12)
Cl10.1066 (7)0.0495 (4)0.0638 (6)0.0242 (4)0.0260 (5)0.0104 (4)
N10.0408 (12)0.0361 (11)0.0350 (12)0.0030 (10)0.0042 (10)0.0054 (10)
N20.0351 (11)0.0342 (11)0.0376 (14)0.0008 (9)0.0044 (10)0.0044 (10)
N30.0405 (12)0.0432 (12)0.0408 (14)0.0010 (10)0.0076 (10)0.0066 (12)
O10.0438 (10)0.0461 (10)0.0436 (13)0.0002 (9)0.0131 (9)0.0006 (9)
O20.0544 (11)0.0449 (10)0.0446 (12)0.0011 (9)0.0081 (10)0.0098 (10)
Geometric parameters (Å, º) top
C1—C21.363 (5)C10—O21.212 (3)
C1—C61.367 (4)C10—O11.327 (3)
C1—H10.9300C11—N21.460 (3)
C2—C31.388 (4)C11—C121.510 (3)
C2—H20.9300C11—H11A0.9700
C3—C41.382 (3)C11—H11B0.9700
C3—H30.9300C12—C151.382 (4)
C4—C51.387 (4)C12—C131.388 (3)
C4—C71.473 (3)C13—C141.373 (4)
C5—C61.378 (4)C13—H130.9300
C5—H50.9300C14—C161.372 (4)
C6—H60.9300C14—H140.9300
C7—N11.350 (3)C15—N31.338 (3)
C7—C81.400 (3)C15—H150.9300
C8—C91.371 (3)C16—N31.321 (3)
C8—H80.9300C16—Cl11.736 (3)
C9—N21.366 (3)N1—N21.342 (3)
C9—C101.473 (4)O1—H1A0.8200
C2—C1—C6120.0 (3)O1—C10—C9110.8 (2)
C2—C1—H1120.0N2—C11—C12113.7 (2)
C6—C1—H1120.0N2—C11—H11A108.8
C1—C2—C3120.2 (3)C12—C11—H11A108.8
C1—C2—H2119.9N2—C11—H11B108.8
C3—C2—H2119.9C12—C11—H11B108.8
C4—C3—C2120.6 (3)H11A—C11—H11B107.7
C4—C3—H3119.7C15—C12—C13117.4 (3)
C2—C3—H3119.7C15—C12—C11121.8 (2)
C3—C4—C5118.1 (3)C13—C12—C11120.8 (2)
C3—C4—C7120.6 (2)C14—C13—C12119.8 (3)
C5—C4—C7121.3 (2)C14—C13—H13120.1
C6—C5—C4120.9 (3)C12—C13—H13120.1
C6—C5—H5119.6C16—C14—C13117.7 (2)
C4—C5—H5119.6C16—C14—H14121.1
C1—C6—C5120.2 (3)C13—C14—H14121.1
C1—C6—H6119.9N3—C15—C12123.5 (2)
C5—C6—H6119.9N3—C15—H15118.2
N1—C7—C8110.2 (2)C12—C15—H15118.2
N1—C7—C4120.2 (2)N3—C16—C14124.5 (3)
C8—C7—C4129.6 (2)N3—C16—Cl1115.7 (2)
C9—C8—C7106.0 (2)C14—C16—Cl1119.8 (2)
C9—C8—H8127.0N2—N1—C7105.52 (19)
C7—C8—H8127.0N1—N2—C9111.93 (19)
N2—C9—C8106.3 (2)N1—N2—C11117.81 (19)
N2—C9—C10124.5 (2)C9—N2—C11130.2 (2)
C8—C9—C10129.1 (2)C16—N3—C15117.0 (2)
O2—C10—O1123.3 (2)C10—O1—H1A109.5
O2—C10—C9125.9 (2)
C6—C1—C2—C30.7 (5)N2—C11—C12—C1383.1 (3)
C1—C2—C3—C40.6 (5)C15—C12—C13—C140.1 (4)
C2—C3—C4—C50.6 (4)C11—C12—C13—C14179.3 (2)
C2—C3—C4—C7179.4 (3)C12—C13—C14—C160.6 (4)
C3—C4—C5—C60.6 (4)C13—C12—C15—N30.7 (4)
C7—C4—C5—C6179.3 (2)C11—C12—C15—N3178.5 (2)
C2—C1—C6—C50.8 (5)C13—C14—C16—N30.5 (4)
C4—C5—C6—C10.7 (5)C13—C14—C16—Cl1178.4 (2)
C3—C4—C7—N1175.6 (2)C8—C7—N1—N20.4 (3)
C5—C4—C7—N14.3 (4)C4—C7—N1—N2178.8 (2)
C3—C4—C7—C85.4 (4)C7—N1—N2—C90.9 (3)
C5—C4—C7—C8174.7 (3)C7—N1—N2—C11178.79 (19)
N1—C7—C8—C90.2 (3)C8—C9—N2—N11.0 (3)
C4—C7—C8—C9179.3 (2)C10—C9—N2—N1178.7 (2)
C7—C8—C9—N20.7 (3)C8—C9—N2—C11178.6 (2)
C7—C8—C9—C10178.3 (2)C10—C9—N2—C113.7 (4)
N2—C9—C10—O26.5 (4)C12—C11—N2—N186.5 (3)
C8—C9—C10—O2176.4 (3)C12—C11—N2—C990.9 (3)
N2—C9—C10—O1174.9 (2)C14—C16—N3—C150.2 (4)
C8—C9—C10—O12.2 (3)Cl1—C16—N3—C15179.12 (18)
N2—C11—C12—C1597.8 (3)C12—C15—N3—C160.8 (4)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1A···N3i0.821.982.794 (3)176
Symmetry code: (i) x+1/4, y+1/4, z+5/4.

Experimental details

Crystal data
Chemical formulaC16H12ClN3O2
Mr313.74
Crystal system, space groupOrthorhombic, Fdd2
Temperature (K)293
a, b, c (Å)20.5430 (5), 54.5902 (15), 5.1134 (1)
V3)5734.4 (2)
Z16
Radiation typeMo Kα
µ (mm1)0.28
Crystal size (mm)0.26 × 0.14 × 0.04
Data collection
DiffractometerBruker APEX2 CCD area-detector
Absorption correctionMulti-scan
(APEX2; Bruker, 2005)
Tmin, Tmax0.931, 0.989
No. of measured, independent and
observed [I > 2σ(I)] reflections
11476, 3276, 2193
Rint0.058
(sin θ/λ)max1)0.649
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.044, 0.095, 1.02
No. of reflections3276
No. of parameters200
No. of restraints1
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.20, 0.16
Absolute structureFlack (1983), with how many Friedel pairs?
Absolute structure parameter0.05 (7)

Computer programs: APEX2 (Bruker, 2005), APEX2, SIR97 (Altomare et al., 1999), SHELXL97 (Sheldrick, 1997), SHELXTL (Bruker, 1997), WinGX (Farrugia, 1999).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1A···N3i0.821.982.794 (3)175.6
Symmetry code: (i) x+1/4, y+1/4, z+5/4.
 

Subscribe to Acta Crystallographica Section E: Crystallographic Communications

The full text of this article is available to subscribers to the journal.

If you have already registered and are using a computer listed in your registration details, please email support@iucr.org for assistance.

Buy online

You may purchase this article in PDF and/or HTML formats. For purchasers in the European Community who do not have a VAT number, VAT will be added at the local rate. Payments to the IUCr are handled by WorldPay, who will accept payment by credit card in several currencies. To purchase the article, please complete the form below (fields marked * are required), and then click on `Continue'.
E-mail address* 
Repeat e-mail address* 
(for error checking) 

Format*   PDF (US $40)
   HTML (US $40)
   PDF+HTML (US $50)
In order for VAT to be shown for your country javascript needs to be enabled.

VAT number 
(non-UK EC countries only) 
Country* 
 

Terms and conditions of use
Contact us

Follow Acta Cryst. E
Sign up for e-alerts
Follow Acta Cryst. on Twitter
Follow us on facebook
Sign up for RSS feeds