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In the title compound, C21H17N3O2, the dihedral angles between the central pyrazole and the substituent pyridine, hydroxy­phenyl and benzene rings are 48.58 (1), 5.2 (1) and 84.73 (1)°, respectively.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806029576/gh2004sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806029576/gh2004Isup2.hkl
Contains datablock I

CCDC reference: 621316

Key indicators

  • Single-crystal X-ray study
  • T = 100 K
  • Mean [sigma](C-C) = 0.002 Å
  • R factor = 0.044
  • wR factor = 0.107
  • Data-to-parameter ratio = 15.9

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ?
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 1 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 1 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 0 ALERT type 3 Indicator that the structure quality may be low 0 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check

Computing details top

Data collection: SMART (Bruker, 2005); cell refinement: SMART; data reduction: SAINT (Bruker, 2005); program(s) used to solve structure: SI2004 (Altomare et al., 1993); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-32 (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).

[3-(2-Hydroxyphenyl)-5-phenyl-4,5-dihydropyrazol-1-yl](pyridin-3-yl)methanone top
Crystal data top
C21H17N3O2F(000) = 720
Mr = 343.38Dx = 1.375 Mg m3
Monoclinic, P21/cMelting point: 168 K
Hall symbol: -P 2ybcMo Kα radiation, λ = 0.71073 Å
a = 5.905 (1) ÅCell parameters from 3690 reflections
b = 19.840 (3) Åθ = 2.5–26.6°
c = 14.283 (2) ŵ = 0.09 mm1
β = 97.516 (3)°T = 100 K
V = 1659.0 (4) Å3Rod, colorless
Z = 40.20 × 0.20 × 0.20 mm
Data collection top
Bruker SMART CCD area-detector
diffractometer
3742 independent reflections
Radiation source: fine-focus sealed tube2687 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.049
φ and ω scansθmax = 27.5°, θmin = 1.8°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 77
Tmin = 0.982, Tmax = 0.982k = 2525
13968 measured reflectionsl = 1818
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.044Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.107H-atom parameters constrained
S = 1.02 w = 1/[σ2(Fo2) + (0.0496P)2 + 0.1984P]
where P = (Fo2 + 2Fc2)/3
3742 reflections(Δ/σ)max < 0.001
236 parametersΔρmax = 0.24 e Å3
0 restraintsΔρmin = 0.24 e Å3
Special details top

Experimental. 1H NMR (300 MHz, DMSO-d6): δ 10.070 (s, 1H), 9.009 (s, 1H,), 8.732 (d, 1H, J = 4.8 Hz), 8.233 (d, 1H, J = 6.9 Hz), 7.583–7.538 (m, 2H), 7.397–7.317 (m, 6H), 6.956–6.895 (m, 2H), 5.755 (dd, 1H, J1 = 11.7 Hz, J2 = 4.8 Hz), 4.065 (d, 1H, J1 = 18.3 Hz, J2 = 11.7 Hz), 3.318 (d, 1H, J = 5.7 Hz).

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
C10.1694 (3)0.08235 (8)0.32846 (11)0.0224 (4)
H1A0.26930.04930.29760.027*
C20.2028 (3)0.10569 (8)0.41685 (12)0.0254 (4)
H20.32460.08800.44670.030*
C30.0618 (3)0.15439 (8)0.46245 (12)0.0265 (4)
H30.08530.17000.52330.032*
C40.1138 (3)0.18002 (8)0.41821 (11)0.0236 (4)
H40.20970.21400.44900.028*
C50.1543 (3)0.15732 (8)0.32926 (11)0.0192 (3)
C60.0101 (3)0.10716 (7)0.28472 (11)0.0191 (3)
C70.3357 (3)0.18746 (7)0.28331 (11)0.0193 (3)
C80.4794 (3)0.24640 (8)0.32096 (11)0.0226 (4)
H8A0.56500.23610.38360.027*
H8B0.38440.28700.32620.027*
C90.6421 (3)0.25620 (8)0.24635 (11)0.0206 (3)
H90.80120.24410.27410.025*
C100.6398 (3)0.32637 (8)0.20576 (11)0.0200 (3)
C110.8302 (3)0.36729 (8)0.22445 (12)0.0239 (4)
H110.96420.35040.26090.029*
C120.8266 (3)0.43256 (8)0.19053 (12)0.0283 (4)
H120.95830.46020.20360.034*
C130.6333 (3)0.45765 (8)0.13795 (12)0.0280 (4)
H130.63130.50260.11510.034*
C140.4419 (3)0.41735 (8)0.11839 (12)0.0269 (4)
H140.30840.43450.08180.032*
C150.4452 (3)0.35182 (8)0.15230 (11)0.0240 (4)
H150.31350.32420.13890.029*
C160.6704 (3)0.18811 (7)0.10113 (11)0.0203 (3)
C170.5629 (3)0.13908 (7)0.02984 (10)0.0195 (3)
C180.3295 (3)0.13668 (8)0.00025 (11)0.0218 (4)
H180.23250.16550.02980.026*
C200.3736 (3)0.05574 (8)0.10932 (12)0.0279 (4)
H200.30800.02570.15710.034*
C210.6074 (3)0.05498 (8)0.08567 (12)0.0261 (4)
H210.70010.02570.11710.031*
C220.7038 (3)0.09771 (8)0.01539 (11)0.0238 (4)
H220.86460.09880.00180.029*
N10.3806 (2)0.16609 (6)0.20245 (9)0.0197 (3)
N20.5547 (2)0.20539 (6)0.17433 (9)0.0208 (3)
N30.2337 (2)0.09623 (7)0.06900 (9)0.0275 (3)
O10.03606 (19)0.08124 (5)0.19886 (7)0.0237 (3)
H10.13960.10240.17620.035*
O20.85361 (18)0.21517 (5)0.09370 (8)0.0248 (3)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0217 (8)0.0211 (8)0.0246 (9)0.0004 (7)0.0041 (7)0.0012 (7)
C20.0255 (9)0.0259 (9)0.0263 (9)0.0011 (7)0.0095 (7)0.0025 (7)
C30.0305 (10)0.0295 (9)0.0207 (8)0.0033 (8)0.0083 (7)0.0011 (7)
C40.0271 (9)0.0236 (8)0.0200 (8)0.0002 (7)0.0021 (7)0.0015 (7)
C50.0200 (8)0.0194 (8)0.0182 (8)0.0032 (6)0.0024 (6)0.0013 (6)
C60.0218 (8)0.0192 (8)0.0166 (8)0.0047 (6)0.0029 (6)0.0000 (6)
C70.0201 (8)0.0195 (8)0.0179 (8)0.0042 (6)0.0009 (6)0.0003 (6)
C80.0253 (9)0.0224 (8)0.0200 (8)0.0009 (7)0.0029 (7)0.0010 (7)
C90.0192 (8)0.0221 (8)0.0204 (8)0.0015 (7)0.0027 (6)0.0022 (6)
C100.0212 (8)0.0207 (8)0.0192 (8)0.0003 (7)0.0068 (6)0.0025 (6)
C110.0203 (9)0.0252 (9)0.0263 (9)0.0009 (7)0.0033 (7)0.0040 (7)
C120.0285 (10)0.0249 (9)0.0333 (10)0.0064 (7)0.0107 (8)0.0054 (7)
C130.0377 (11)0.0204 (8)0.0284 (9)0.0022 (8)0.0133 (8)0.0008 (7)
C140.0291 (9)0.0278 (9)0.0243 (9)0.0065 (8)0.0051 (7)0.0015 (7)
C150.0223 (9)0.0258 (9)0.0242 (9)0.0006 (7)0.0032 (7)0.0028 (7)
C160.0210 (9)0.0171 (7)0.0233 (8)0.0033 (7)0.0051 (6)0.0026 (6)
C170.0225 (8)0.0197 (8)0.0170 (8)0.0001 (7)0.0047 (6)0.0036 (6)
C180.0231 (9)0.0256 (8)0.0181 (8)0.0011 (7)0.0073 (6)0.0023 (7)
C200.0330 (10)0.0321 (9)0.0194 (8)0.0048 (8)0.0058 (7)0.0041 (7)
C210.0299 (10)0.0268 (9)0.0239 (9)0.0017 (7)0.0120 (7)0.0022 (7)
C220.0220 (9)0.0263 (9)0.0246 (9)0.0016 (7)0.0083 (7)0.0018 (7)
N10.0187 (7)0.0205 (7)0.0203 (7)0.0004 (6)0.0043 (5)0.0011 (5)
N20.0194 (7)0.0198 (7)0.0243 (7)0.0039 (6)0.0066 (6)0.0027 (5)
N30.0264 (8)0.0361 (8)0.0202 (7)0.0006 (7)0.0039 (6)0.0031 (6)
O10.0282 (7)0.0240 (6)0.0202 (6)0.0036 (5)0.0082 (5)0.0030 (5)
O20.0198 (6)0.0242 (6)0.0315 (7)0.0033 (5)0.0079 (5)0.0006 (5)
Geometric parameters (Å, º) top
C1—C21.383 (2)C11—H110.9500
C1—C61.389 (2)C12—C131.375 (2)
C1—H1A0.9500C12—H120.9500
C2—C31.382 (2)C13—C141.383 (2)
C2—H20.9500C13—H130.9500
C3—C41.380 (2)C14—C151.387 (2)
C3—H30.9500C14—H140.9500
C4—C51.398 (2)C15—H150.9500
C4—H40.9500C16—O21.2247 (18)
C5—C61.407 (2)C16—N21.3655 (19)
C5—C71.456 (2)C16—C171.489 (2)
C6—O11.3567 (18)C17—C221.387 (2)
C7—N11.2900 (19)C17—C181.390 (2)
C7—C81.502 (2)C18—N31.335 (2)
C8—C91.538 (2)C18—H180.9500
C8—H8A0.9900C20—N31.336 (2)
C8—H8B0.9900C20—C211.378 (2)
C9—N21.4839 (19)C20—H200.9500
C9—C101.508 (2)C21—C221.379 (2)
C9—H91.0000C21—H210.9500
C10—C111.384 (2)C22—H220.9500
C10—C151.389 (2)N1—N21.3906 (17)
C11—C121.382 (2)O1—H10.8400
C2—C1—C6120.02 (15)C10—C11—H11119.8
C2—C1—H1A120.0C13—C12—C11120.27 (16)
C6—C1—H1A120.0C13—C12—H12119.9
C3—C2—C1121.01 (16)C11—C12—H12119.9
C3—C2—H2119.5C12—C13—C14119.96 (16)
C1—C2—H2119.5C12—C13—H13120.0
C4—C3—C2118.98 (15)C14—C13—H13120.0
C4—C3—H3120.5C13—C14—C15119.85 (16)
C2—C3—H3120.5C13—C14—H14120.1
C3—C4—C5121.71 (16)C15—C14—H14120.1
C3—C4—H4119.1C14—C15—C10120.37 (15)
C5—C4—H4119.1C14—C15—H15119.8
C4—C5—C6118.28 (15)C10—C15—H15119.8
C4—C5—C7120.06 (15)O2—C16—N2119.51 (14)
C6—C5—C7121.61 (14)O2—C16—C17121.97 (14)
O1—C6—C1117.08 (14)N2—C16—C17118.45 (13)
O1—C6—C5122.94 (14)C22—C17—C18117.81 (15)
C1—C6—C5119.98 (14)C22—C17—C16118.51 (14)
N1—C7—C5121.22 (14)C18—C17—C16123.41 (14)
N1—C7—C8113.80 (14)N3—C18—C17123.75 (15)
C5—C7—C8124.94 (13)N3—C18—H18118.1
C7—C8—C9103.02 (12)C17—C18—H18118.1
C7—C8—H8A111.2N3—C20—C21123.88 (16)
C9—C8—H8A111.2N3—C20—H20118.1
C7—C8—H8B111.2C21—C20—H20118.1
C9—C8—H8B111.2C20—C21—C22118.45 (15)
H8A—C8—H8B109.1C20—C21—H21120.8
N2—C9—C10112.08 (12)C22—C21—H21120.8
N2—C9—C8101.67 (12)C21—C22—C17119.20 (15)
C10—C9—C8114.09 (13)C21—C22—H22120.4
N2—C9—H9109.6C17—C22—H22120.4
C10—C9—H9109.6C7—N1—N2108.71 (13)
C8—C9—H9109.6C16—N2—N1122.91 (12)
C11—C10—C15119.06 (15)C16—N2—C9122.53 (12)
C11—C10—C9120.08 (14)N1—N2—C9112.57 (11)
C15—C10—C9120.82 (14)C18—N3—C20116.89 (14)
C12—C11—C10120.50 (16)C6—O1—H1109.5
C12—C11—H11119.8
 

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