Literature DB >> 21581336

[3-(4-Chloro-phen-yl)-5-hydr-oxy-5-phenyl-4,5-dihydro-1H-pyrazol-1-yl](3-pyrid-yl)methanone.

Hoong-Kun Fun, Samuel Robinson Jebas, Jyothi N Rao, B Kalluraya.

Abstract

In the title compound, C(21)H(16)ClN(3)O(2), the dihedral angles formed by the pyrazole ring with the pyridyl, phenyl-ene and phenyl rings are 6.80 (5), 9.23 (5) and 74.96 (5)°, respectively. The phenyl and phenyl-ene rings are inclined at 80.14 (2)°. Intra-molecular O-H⋯O and C-H⋯N hydrogen bonds generate S(6) ring motifs. The crystal packing is strengthened by short inter-molecular O-H⋯N, C-H⋯O hydrogen bonds and π-π stacking inter-actions with centroid-centroid distances of 3.6247 (5)-3.7205 (5) Å, together with inter-molecular short O⋯N contacts [2.7682 (11) Å]. Mol-ecules are linked into infinite chains along [100].

Entities: Chemical Disease Gene

Year: 2008 PMID： 21581336 PMCID： PMC2959893 DOI： 10.1107/S1600536808037161

Source DB: PubMed Journal: Acta Crystallogr Sect E Struct Rep Online ISSN： 1600-5368

Related literature

For the biological applications of pyrazoles, see: Kalluraya & Ramesh (2001 ▶); Watanabe et al. (1998 ▶); Yuhong & Rajender (2005 ▶). For bond-length data, see: Allen et al. (1987 ▶). For graph-set analysis of hydrogen bonding, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C21H16ClN3O2 M = 377.82 Triclinic, a = 7.5916 (1) Å b = 9.7644 (1) Å c = 12.5474 (2) Å α = 104.424 (1)° β = 94.960 (1)° γ = 96.081 (1)° V = 889.55 (2) Å3 Z = 2 Mo Kα radiation μ = 0.24 mm−1 T = 100.0 (1) K 0.47 × 0.29 × 0.19 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T min = 0.896, T max = 0.957 20326 measured reflections 6385 independent reflections 5630 reflections with I > 2σ(I) R int = 0.023

Refinement

R[F 2 > 2σ(F 2)] = 0.037 wR(F 2) = 0.103 S = 1.04 6385 reflections 248 parameters 1 restraint H atoms treated by a mixture of independent and constrained refinement Δρmax = 0.54 e Å−3 Δρmin = −0.26 e Å−3 Data collection: APEX2 (Bruker, 2005 ▶); cell refinement: APEX2; data reduction: SAINT (Bruker, 2005 ▶); program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2003 ▶). Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808037161/ng2515sup1.cif Structure factors: contains datablocks I. DOI: 10.1107/S1600536808037161/ng2515Isup2.hkl Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C₂₁H₁₆ClN₃O₂	Z = 2
M_r = 377.82	F₀₀₀ = 392
Triclinic, P1	D_x = 1.411 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation λ = 0.71073 Å
a = 7.5916 (1) Å	Cell parameters from 9943 reflections
b = 9.7644 (1) Å	θ = 3.1–37.5º
c = 12.5474 (2) Å	µ = 0.24 mm⁻¹
α = 104.424 (1)º	T = 100.0 (1) K
β = 94.960 (1)º	Block, colourless
γ = 96.081 (1)º	0.47 × 0.29 × 0.19 mm
V = 889.55 (2) Å³

Bruker SMART APEXII CCD area-detector diffractometer	6385 independent reflections
Radiation source: fine-focus sealed tube	5630 reflections with I > 2σ(I)
Monochromator: graphite	R_int = 0.023
T = 100.0(1) K	θ_max = 32.5º
φ and ω scans	θ_min = 1.7º
Absorption correction: multi-scan(SADABS; Bruker, 2005)	h = −11→11
T_min = 0.896, T_max = 0.957	k = −14→14
20326 measured reflections	l = −18→18

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.037	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.104	w = 1/[σ²(F_o²) + (0.0577P)² + 0.2362P] where P = (F_o² + 2F_c²)/3
S = 1.04	(Δ/σ)_max < 0.001
6385 reflections	Δρ_max = 0.54 e Å⁻³
248 parameters	Δρ_min = −0.26 e Å⁻³
1 restraint	Extinction correction: none
Primary atom site location: structure-invariant direct methods

Experimental. The data was collected with the Oxford Cyrosystem Cobra low-temperature attachment.

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.

	x	y	z	U_iso*/U_eq
Cl1	−0.18759 (3)	0.58111 (2)	1.24148 (2)	0.02272 (7)
O1	0.24543 (9)	−0.22304 (7)	0.66899 (5)	0.01553 (13)
O2	0.47798 (8)	−0.05281 (7)	0.85593 (5)	0.01450 (12)
N1	0.05961 (10)	0.04156 (8)	0.85564 (6)	0.01321 (13)
N2	0.17594 (9)	−0.03622 (8)	0.79391 (6)	0.01266 (13)
N3	−0.36717 (10)	−0.27300 (9)	0.73008 (7)	0.01823 (15)
C1	−0.11452 (12)	0.23011 (9)	1.01516 (7)	0.01448 (15)
H1A	−0.1821	0.1448	0.9752	0.017*
C2	−0.19255 (12)	0.32951 (10)	1.08935 (7)	0.01548 (16)
H2A	−0.3119	0.3113	1.0994	0.019*
C3	−0.08985 (13)	0.45689 (9)	1.14851 (7)	0.01577 (16)
C4	0.08865 (13)	0.48666 (9)	1.13548 (7)	0.01624 (16)
H4A	0.1555	0.5722	1.1756	0.019*
C5	0.16553 (12)	0.38617 (9)	1.06134 (7)	0.01500 (15)
H5A	0.2852	0.4047	1.0523	0.018*
C6	0.06584 (11)	0.25743 (9)	1.00002 (7)	0.01290 (14)
C7	0.15147 (11)	0.15330 (9)	0.92314 (7)	0.01247 (14)
C8	0.34900 (11)	0.16151 (9)	0.91685 (7)	0.01392 (15)
H8A	0.4118	0.1521	0.9848	0.017*
H8B	0.3961	0.2510	0.9030	0.017*
C9	0.36523 (11)	0.03425 (9)	0.81857 (7)	0.01211 (14)
C10	0.42505 (12)	0.08305 (9)	0.71939 (7)	0.01367 (15)
C11	0.60717 (13)	0.11624 (10)	0.71445 (8)	0.01826 (17)
H11A	0.6901	0.1036	0.7690	0.022*
C12	0.66489 (15)	0.16839 (11)	0.62776 (9)	0.0236 (2)
H12A	0.7863	0.1903	0.6248	0.028*
C13	0.54216 (16)	0.18775 (11)	0.54588 (8)	0.0245 (2)
H13A	0.5810	0.2208	0.4874	0.029*
C14	0.36126 (16)	0.15747 (11)	0.55197 (8)	0.0227 (2)
H14A	0.2786	0.1718	0.4979	0.027*
C15	0.30233 (13)	0.10574 (10)	0.63848 (8)	0.01771 (16)
H15A	0.1807	0.0863	0.6422	0.021*
C16	0.12920 (11)	−0.16587 (9)	0.71942 (7)	0.01213 (14)
C17	−0.05871 (11)	−0.24069 (9)	0.69814 (7)	0.01225 (14)
C18	−0.08787 (12)	−0.36918 (10)	0.61570 (8)	0.01686 (16)
H18A	0.0050	−0.4016	0.5768	0.020*
C19	−0.25619 (13)	−0.44831 (10)	0.59202 (8)	0.01974 (18)
H19A	−0.2776	−0.5344	0.5376	0.024*
C20	−0.39171 (12)	−0.39616 (10)	0.65129 (8)	0.01884 (17)
H20A	−0.5044	−0.4492	0.6355	0.023*
C21	−0.20374 (11)	−0.19778 (10)	0.75323 (8)	0.01554 (16)
H21A	−0.1862	−0.1128	0.8088	0.019*
H1O2	0.488 (2)	−0.1208 (13)	0.8037 (10)	0.026 (4)*

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.02952 (12)	0.01698 (11)	0.02199 (12)	0.00842 (8)	0.01020 (9)	0.00106 (8)
O1	0.0147 (3)	0.0150 (3)	0.0160 (3)	0.0030 (2)	0.0043 (2)	0.0011 (2)
O2	0.0147 (3)	0.0148 (3)	0.0141 (3)	0.0036 (2)	0.0005 (2)	0.0036 (2)
N1	0.0140 (3)	0.0118 (3)	0.0129 (3)	0.0026 (2)	0.0031 (2)	0.0008 (2)
N2	0.0110 (3)	0.0120 (3)	0.0133 (3)	0.0011 (2)	0.0025 (2)	0.0000 (2)
N3	0.0120 (3)	0.0183 (4)	0.0217 (4)	0.0009 (3)	−0.0001 (3)	0.0015 (3)
C1	0.0157 (3)	0.0130 (4)	0.0143 (4)	0.0018 (3)	0.0019 (3)	0.0028 (3)
C2	0.0169 (4)	0.0154 (4)	0.0151 (4)	0.0038 (3)	0.0035 (3)	0.0045 (3)
C3	0.0218 (4)	0.0131 (4)	0.0134 (4)	0.0057 (3)	0.0045 (3)	0.0030 (3)
C4	0.0214 (4)	0.0118 (4)	0.0146 (4)	0.0016 (3)	0.0029 (3)	0.0015 (3)
C5	0.0170 (4)	0.0126 (4)	0.0142 (4)	0.0007 (3)	0.0022 (3)	0.0018 (3)
C6	0.0156 (3)	0.0113 (3)	0.0115 (3)	0.0022 (3)	0.0019 (3)	0.0023 (3)
C7	0.0141 (3)	0.0115 (3)	0.0118 (3)	0.0018 (3)	0.0019 (3)	0.0027 (3)
C8	0.0135 (3)	0.0138 (4)	0.0123 (3)	0.0003 (3)	0.0017 (3)	0.0000 (3)
C9	0.0111 (3)	0.0126 (3)	0.0121 (3)	0.0006 (3)	0.0012 (3)	0.0026 (3)
C10	0.0172 (4)	0.0110 (3)	0.0124 (3)	0.0010 (3)	0.0033 (3)	0.0021 (3)
C11	0.0186 (4)	0.0180 (4)	0.0175 (4)	−0.0013 (3)	0.0045 (3)	0.0039 (3)
C12	0.0289 (5)	0.0178 (4)	0.0233 (5)	−0.0033 (4)	0.0120 (4)	0.0035 (3)
C13	0.0433 (6)	0.0135 (4)	0.0177 (4)	−0.0002 (4)	0.0113 (4)	0.0047 (3)
C14	0.0382 (6)	0.0153 (4)	0.0153 (4)	0.0045 (4)	0.0017 (4)	0.0055 (3)
C15	0.0228 (4)	0.0149 (4)	0.0156 (4)	0.0031 (3)	0.0017 (3)	0.0043 (3)
C16	0.0133 (3)	0.0116 (3)	0.0111 (3)	0.0014 (3)	0.0011 (3)	0.0023 (3)
C17	0.0122 (3)	0.0115 (3)	0.0123 (3)	0.0017 (3)	0.0002 (3)	0.0022 (3)
C18	0.0165 (4)	0.0141 (4)	0.0169 (4)	0.0008 (3)	0.0013 (3)	−0.0009 (3)
C19	0.0192 (4)	0.0150 (4)	0.0203 (4)	−0.0015 (3)	−0.0008 (3)	−0.0017 (3)
C20	0.0149 (4)	0.0181 (4)	0.0205 (4)	−0.0017 (3)	−0.0023 (3)	0.0025 (3)
C21	0.0126 (3)	0.0143 (4)	0.0177 (4)	0.0016 (3)	0.0006 (3)	0.0007 (3)

Cl1—C3	1.7373 (9)	C8—H8A	0.9700
O1—C16	1.2311 (10)	C8—H8B	0.9700
O2—C9	1.3994 (11)	C9—C10	1.5262 (12)
O2—H1O2	0.823 (9)	C10—C15	1.3928 (13)
N1—C7	1.2924 (11)	C10—C11	1.3965 (12)
N1—N2	1.3870 (10)	C11—C12	1.3948 (13)
N2—C16	1.3638 (11)	C11—H11A	0.9300
N2—C9	1.4972 (11)	C12—C13	1.3885 (17)
N3—C20	1.3367 (12)	C12—H12A	0.9300
N3—C21	1.3422 (11)	C13—C14	1.3866 (16)
C1—C2	1.3880 (12)	C13—H13A	0.9300
C1—C6	1.4053 (12)	C14—C15	1.3938 (13)
C1—H1A	0.9300	C14—H14A	0.9300
C2—C3	1.3929 (13)	C15—H15A	0.9300
C2—H2A	0.9300	C16—C17	1.5021 (11)
C3—C4	1.3879 (13)	C17—C18	1.3957 (12)
C4—C5	1.3889 (12)	C17—C21	1.3966 (12)
C4—H4A	0.9300	C18—C19	1.3889 (12)
C5—C6	1.4003 (12)	C18—H18A	0.9300
C5—H5A	0.9300	C19—C20	1.3876 (14)
C6—C7	1.4652 (12)	C19—H19A	0.9300
C7—C8	1.5032 (12)	C20—H20A	0.9300
C8—C9	1.5412 (12)	C21—H21A	0.9300

C9—O2—H1O2	108.8 (10)	C10—C9—C8	111.83 (7)
C7—N1—N2	108.27 (7)	C15—C10—C11	119.31 (8)
C16—N2—N1	125.12 (7)	C15—C10—C9	121.51 (8)
C16—N2—C9	121.54 (7)	C11—C10—C9	118.99 (8)
N1—N2—C9	113.32 (7)	C12—C11—C10	120.09 (9)
C20—N3—C21	118.29 (8)	C12—C11—H11A	120.0
C2—C1—C6	120.46 (8)	C10—C11—H11A	120.0
C2—C1—H1A	119.8	C13—C12—C11	120.40 (10)
C6—C1—H1A	119.8	C13—C12—H12A	119.8
C1—C2—C3	119.15 (8)	C11—C12—H12A	119.8
C1—C2—H2A	120.4	C14—C13—C12	119.51 (9)
C3—C2—H2A	120.4	C14—C13—H13A	120.2
C4—C3—C2	121.67 (8)	C12—C13—H13A	120.2
C4—C3—Cl1	119.23 (7)	C13—C14—C15	120.49 (10)
C2—C3—Cl1	119.10 (7)	C13—C14—H14A	119.8
C3—C4—C5	118.69 (8)	C15—C14—H14A	119.8
C3—C4—H4A	120.7	C10—C15—C14	120.18 (9)
C5—C4—H4A	120.7	C10—C15—H15A	119.9
C4—C5—C6	121.12 (8)	C14—C15—H15A	119.9
C4—C5—H5A	119.4	O1—C16—N2	118.64 (8)
C6—C5—H5A	119.4	O1—C16—C17	119.41 (8)
C5—C6—C1	118.91 (8)	N2—C16—C17	121.95 (7)
C5—C6—C7	119.70 (8)	C18—C17—C21	117.32 (8)
C1—C6—C7	121.37 (8)	C18—C17—C16	115.35 (7)
N1—C7—C6	121.37 (8)	C21—C17—C16	127.30 (8)
N1—C7—C8	113.88 (7)	C19—C18—C17	119.68 (9)
C6—C7—C8	124.71 (7)	C19—C18—H18A	120.2
C7—C8—C9	103.47 (7)	C17—C18—H18A	120.2
C7—C8—H8A	111.1	C20—C19—C18	118.56 (9)
C9—C8—H8A	111.1	C20—C19—H19A	120.7
C7—C8—H8B	111.1	C18—C19—H19A	120.7
C9—C8—H8B	111.1	N3—C20—C19	122.80 (8)
H8A—C8—H8B	109.0	N3—C20—H20A	118.6
O2—C9—N2	111.30 (7)	C19—C20—H20A	118.6
O2—C9—C10	113.38 (7)	N3—C21—C17	123.34 (8)
N2—C9—C10	110.73 (7)	N3—C21—H21A	118.3
O2—C9—C8	108.31 (7)	C17—C21—H21A	118.3
N2—C9—C8	100.55 (6)

C7—N1—N2—C16	175.28 (8)	N2—C9—C10—C15	21.78 (11)
C7—N1—N2—C9	−3.15 (10)	C8—C9—C10—C15	−89.47 (10)
C6—C1—C2—C3	0.11 (13)	O2—C9—C10—C11	−37.34 (11)
C1—C2—C3—C4	−0.26 (14)	N2—C9—C10—C11	−163.27 (8)
C1—C2—C3—Cl1	−179.91 (7)	C8—C9—C10—C11	85.48 (10)
C2—C3—C4—C5	0.00 (14)	C15—C10—C11—C12	−1.49 (14)
Cl1—C3—C4—C5	179.66 (7)	C9—C10—C11—C12	−176.55 (8)
C3—C4—C5—C6	0.41 (14)	C10—C11—C12—C13	0.03 (15)
C4—C5—C6—C1	−0.56 (13)	C11—C12—C13—C14	1.25 (15)
C4—C5—C6—C7	−179.54 (8)	C12—C13—C14—C15	−1.05 (15)
C2—C1—C6—C5	0.29 (13)	C11—C10—C15—C14	1.69 (14)
C2—C1—C6—C7	179.26 (8)	C9—C10—C15—C14	176.63 (8)
N2—N1—C7—C6	179.99 (7)	C13—C14—C15—C10	−0.43 (14)
N2—N1—C7—C8	−1.91 (10)	N1—N2—C16—O1	179.18 (8)
C5—C6—C7—N1	−171.57 (8)	C9—N2—C16—O1	−2.51 (12)
C1—C6—C7—N1	9.47 (13)	N1—N2—C16—C17	−1.32 (13)
C5—C6—C7—C8	10.55 (13)	C9—N2—C16—C17	176.99 (7)
C1—C6—C7—C8	−168.42 (8)	O1—C16—C17—C18	−3.55 (12)
N1—C7—C8—C9	5.84 (10)	N2—C16—C17—C18	176.95 (8)
C6—C7—C8—C9	−176.14 (8)	O1—C16—C17—C21	174.65 (9)
C16—N2—C9—O2	−57.55 (10)	N2—C16—C17—C21	−4.85 (14)
N1—N2—C9—O2	120.95 (8)	C21—C17—C18—C19	−0.15 (14)
C16—N2—C9—C10	69.54 (10)	C16—C17—C18—C19	178.25 (8)
N1—N2—C9—C10	−111.97 (8)	C17—C18—C19—C20	0.35 (15)
C16—N2—C9—C8	−172.11 (8)	C21—N3—C20—C19	−0.70 (15)
N1—N2—C9—C8	6.39 (9)	C18—C19—C20—N3	0.08 (16)
C7—C8—C9—O2	−123.48 (7)	C20—N3—C21—C17	0.92 (14)
C7—C8—C9—N2	−6.68 (8)	C18—C17—C21—N3	−0.51 (14)
C7—C8—C9—C10	110.87 (8)	C16—C17—C21—N3	−178.68 (9)
O2—C9—C10—C15	147.71 (8)

D—H···A	D—H	H···A	D···A	D—H···A
O2—H1O2···O1	0.824 (13)	2.340 (14)	2.8463 (9)	120.3 (13)
O2—H1O2···N3ⁱ	0.824 (13)	2.027 (14)	2.7682 (11)	149.5 (14)
C8—H8A···O2ⁱⁱ	0.97	2.55	3.4836 (11)	163
C13—H13A···O1ⁱⁱⁱ	0.93	2.46	3.3294 (12)	156
C21—H21A···N1	0.93	2.21	2.8600 (12)	127
C14—H14A···Cg2^iv	0.93	2.90	3.6968 (11)	144

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H1O2⋯O1	0.824 (13)	2.340 (14)	2.8463 (9)	120.3 (13)
O2—H1O2⋯N3ⁱ	0.824 (13)	2.027 (14)	2.7682 (11)	149.5 (14)
C8—H8A⋯O2ⁱⁱ	0.97	2.55	3.4836 (11)	163
C13—H13A⋯O1ⁱⁱⁱ	0.93	2.46	3.3294 (12)	156
C21—H21A⋯N1	0.93	2.21	2.8600 (12)	127
C14—H14A⋯Cg2^iv	0.93	2.90	3.6968 (11)	144

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) . Cg2 is the centroid of the N3/C17–C21 ring.

2 in total

1. A short history of SHELX.

Authors: George M Sheldrick
Journal: Acta Crystallogr A Date: 2007-12-21 Impact factor: 2.290

2. 4-Benzylamino-1-chloro-6-substituted phthalazines: synthesis and inhibitory activity toward phosphodiesterase 5.

Authors: N Watanabe; Y Kabasawa; Y Takase; M Matsukura; K Miyazaki; H Ishihara; K Kodama; H Adachi
Journal: J Med Chem Date: 1998-08-27 Impact factor: 7.446

2 in total