organic compounds
4-[(3,4-Dimethoxybenzylidene)amino]-1,5-dimethyl-2-phenyl-1H-pyrazol-3(2H)-one
aChemistry Department, Faculty of Science, King Abdul Aziz University, PO Box 80203, Jeddah 21589, Saudi Arabia, and bDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
*Correspondence e-mail: seikweng@um.edu.my
The imino–carbon double-bond in the title Schiff base, C20H21N3O3, has an E configuration; the six-membered aromatic substituent (r.m.s. deviation = 0.012 Å) is nearly coplanar with five-membered pyrazole substituent (r.m.s. deviation = 0.031 Å), the dihedral angle between the two systems being 11.4 (1)°]. The phenyl ring connected to the pyrazole ring is aligned at 45.5 (1)° with respect to this five-membered ring. The N atoms in the ring show pyramidal coordinations.
Experimental
Crystal data
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Data collection: APEX2 (Bruker, 2009); cell SAINT (Bruker, 2009); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: X-SEED (Barbour, 2001); software used to prepare material for publication: publCIF (Westrip, 2010).
Supporting information
10.1107/S1600536810023238/cv2733sup1.cif
contains datablocks global, I. DOI:Structure factors: contains datablock I. DOI: 10.1107/S1600536810023238/cv2733Isup2.hkl
3,4-Dimethoxybenzaldehyde (0.36 g, 2.2 mmol) and 4-aminoantipyrine (0.45 g, 2.2 mmol) here heated in methanol (15 ml) for 5 h to afford a colorless precipitate. The solid material was collected and recrystallized from methanol.
Carbon-bound H-atoms were placed in calculated positions [C–H 0.95 to 0.98 Å, U(H) 1.2 to 1.5Ueq(C)] and were included in the
in the riding model approximation.Data collection: APEX2 (Bruker, 2009); cell
SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: X-SEED (Barbour, 2001); software used to prepare material for publication: publCIF (Westrip, 2010).Fig. 1. Displacement ellipsoid plot (Barbour, 2001) of C20H21N3O3 at the 70% probability level; hydrogen atoms are drawn as spheres of arbitrary radius. |
C20H21N3O3 | F(000) = 744 |
Mr = 351.40 | Dx = 1.286 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 6153 reflections |
a = 12.5584 (8) Å | θ = 2.4–28.2° |
b = 10.4752 (7) Å | µ = 0.09 mm−1 |
c = 14.6002 (9) Å | T = 100 K |
β = 109.039 (1)° | Prism, colourless |
V = 1815.6 (2) Å3 | 0.35 × 0.25 × 0.15 mm |
Z = 4 |
Bruker SMART APEX diffractometer | 3442 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.031 |
Graphite monochromator | θmax = 27.5°, θmin = 1.7° |
ω scans | h = −16→16 |
16900 measured reflections | k = −13→12 |
4164 independent reflections | l = −18→17 |
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)] = 0.037 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.103 | H-atom parameters constrained |
S = 1.00 | w = 1/[σ2(Fo2) + (0.0548P)2 + 0.5659P] where P = (Fo2 + 2Fc2)/3 |
4164 reflections | (Δ/σ)max = 0.001 |
239 parameters | Δρmax = 0.23 e Å−3 |
0 restraints | Δρmin = −0.24 e Å−3 |
C20H21N3O3 | V = 1815.6 (2) Å3 |
Mr = 351.40 | Z = 4 |
Monoclinic, P21/c | Mo Kα radiation |
a = 12.5584 (8) Å | µ = 0.09 mm−1 |
b = 10.4752 (7) Å | T = 100 K |
c = 14.6002 (9) Å | 0.35 × 0.25 × 0.15 mm |
β = 109.039 (1)° |
Bruker SMART APEX diffractometer | 3442 reflections with I > 2σ(I) |
16900 measured reflections | Rint = 0.031 |
4164 independent reflections |
R[F2 > 2σ(F2)] = 0.037 | 0 restraints |
wR(F2) = 0.103 | H-atom parameters constrained |
S = 1.00 | Δρmax = 0.23 e Å−3 |
4164 reflections | Δρmin = −0.24 e Å−3 |
239 parameters |
x | y | z | Uiso*/Ueq | ||
O1 | 0.28425 (6) | 0.77513 (8) | 0.59527 (6) | 0.01980 (19) | |
O2 | 0.86240 (7) | 0.62990 (8) | 0.50221 (6) | 0.02147 (19) | |
O3 | 0.86452 (8) | 0.84966 (8) | 0.42541 (7) | 0.0292 (2) | |
N1 | 0.26678 (8) | 0.60441 (9) | 0.69085 (7) | 0.0185 (2) | |
N2 | 0.33485 (8) | 0.50111 (9) | 0.73701 (7) | 0.0190 (2) | |
N3 | 0.50498 (8) | 0.62594 (9) | 0.60372 (7) | 0.0187 (2) | |
C1 | 0.18777 (9) | 0.65675 (11) | 0.73138 (8) | 0.0189 (2) | |
C2 | 0.09077 (9) | 0.71284 (11) | 0.66951 (9) | 0.0204 (2) | |
H2 | 0.0778 | 0.7155 | 0.6017 | 0.025* | |
C3 | 0.01286 (10) | 0.76508 (12) | 0.70792 (9) | 0.0235 (3) | |
H3 | −0.0530 | 0.8052 | 0.6662 | 0.028* | |
C4 | 0.03033 (10) | 0.75915 (12) | 0.80662 (9) | 0.0252 (3) | |
H4 | −0.0240 | 0.7936 | 0.8323 | 0.030* | |
C5 | 0.12751 (11) | 0.70267 (13) | 0.86781 (9) | 0.0258 (3) | |
H5 | 0.1394 | 0.6982 | 0.9354 | 0.031* | |
C6 | 0.20713 (10) | 0.65278 (12) | 0.83089 (9) | 0.0230 (3) | |
H6 | 0.2745 | 0.6161 | 0.8731 | 0.028* | |
C7 | 0.31965 (9) | 0.67280 (11) | 0.63587 (8) | 0.0171 (2) | |
C8 | 0.41934 (9) | 0.59911 (11) | 0.64197 (8) | 0.0173 (2) | |
C9 | 0.42229 (9) | 0.49573 (11) | 0.70009 (8) | 0.0179 (2) | |
C10 | 0.50361 (10) | 0.38826 (12) | 0.72347 (9) | 0.0231 (3) | |
H10A | 0.5663 | 0.4077 | 0.6996 | 0.035* | |
H10B | 0.4657 | 0.3102 | 0.6924 | 0.035* | |
H10C | 0.5326 | 0.3759 | 0.7938 | 0.035* | |
C11 | 0.27490 (10) | 0.38645 (11) | 0.75111 (9) | 0.0225 (3) | |
H11A | 0.2343 | 0.4054 | 0.7965 | 0.034* | |
H11B | 0.3292 | 0.3177 | 0.7774 | 0.034* | |
H11C | 0.2212 | 0.3597 | 0.6888 | 0.034* | |
C12 | 0.49724 (9) | 0.72136 (11) | 0.54678 (8) | 0.0191 (2) | |
H12 | 0.4304 | 0.7713 | 0.5274 | 0.023* | |
C13 | 0.59014 (9) | 0.75419 (11) | 0.51128 (8) | 0.0187 (2) | |
C14 | 0.68242 (9) | 0.67130 (11) | 0.52633 (8) | 0.0182 (2) | |
H14 | 0.6838 | 0.5919 | 0.5582 | 0.022* | |
C15 | 0.77102 (9) | 0.70504 (11) | 0.49495 (8) | 0.0186 (2) | |
C16 | 0.77122 (10) | 0.82494 (11) | 0.45064 (9) | 0.0213 (2) | |
C17 | 0.68007 (11) | 0.90626 (12) | 0.43516 (9) | 0.0241 (3) | |
H17 | 0.6794 | 0.9867 | 0.4049 | 0.029* | |
C18 | 0.58924 (10) | 0.86946 (11) | 0.46420 (9) | 0.0222 (3) | |
H18 | 0.5257 | 0.9242 | 0.4515 | 0.027* | |
C19 | 0.87115 (10) | 0.51317 (11) | 0.55464 (9) | 0.0229 (3) | |
H19A | 0.9404 | 0.4687 | 0.5564 | 0.034* | |
H19B | 0.8060 | 0.4590 | 0.5226 | 0.034* | |
H19C | 0.8730 | 0.5316 | 0.6209 | 0.034* | |
C20 | 0.86692 (15) | 0.96944 (14) | 0.37878 (14) | 0.0452 (4) | |
H20A | 0.9381 | 0.9775 | 0.3652 | 0.068* | |
H20B | 0.8605 | 1.0393 | 0.4213 | 0.068* | |
H20C | 0.8038 | 0.9735 | 0.3179 | 0.068* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0190 (4) | 0.0167 (4) | 0.0230 (4) | 0.0009 (3) | 0.0060 (3) | 0.0034 (3) |
O2 | 0.0217 (4) | 0.0182 (4) | 0.0269 (4) | 0.0041 (3) | 0.0112 (3) | 0.0044 (3) |
O3 | 0.0333 (5) | 0.0184 (4) | 0.0463 (6) | 0.0023 (4) | 0.0273 (4) | 0.0066 (4) |
N1 | 0.0171 (4) | 0.0173 (5) | 0.0208 (5) | 0.0008 (4) | 0.0060 (4) | 0.0036 (4) |
N2 | 0.0183 (4) | 0.0165 (5) | 0.0216 (5) | 0.0006 (4) | 0.0057 (4) | 0.0036 (4) |
N3 | 0.0178 (4) | 0.0192 (5) | 0.0192 (5) | −0.0019 (4) | 0.0062 (4) | −0.0020 (4) |
C1 | 0.0170 (5) | 0.0173 (5) | 0.0228 (6) | −0.0038 (4) | 0.0071 (4) | −0.0013 (5) |
C2 | 0.0188 (5) | 0.0214 (6) | 0.0208 (6) | −0.0040 (4) | 0.0060 (4) | −0.0001 (5) |
C3 | 0.0176 (5) | 0.0232 (6) | 0.0293 (6) | −0.0018 (5) | 0.0071 (5) | −0.0010 (5) |
C4 | 0.0241 (6) | 0.0237 (6) | 0.0319 (7) | −0.0058 (5) | 0.0147 (5) | −0.0083 (5) |
C5 | 0.0302 (6) | 0.0271 (7) | 0.0212 (6) | −0.0061 (5) | 0.0097 (5) | −0.0051 (5) |
C6 | 0.0220 (6) | 0.0236 (6) | 0.0211 (6) | −0.0021 (5) | 0.0039 (5) | −0.0013 (5) |
C7 | 0.0164 (5) | 0.0169 (5) | 0.0167 (5) | −0.0032 (4) | 0.0038 (4) | −0.0016 (4) |
C8 | 0.0163 (5) | 0.0172 (5) | 0.0174 (5) | −0.0008 (4) | 0.0042 (4) | −0.0013 (4) |
C9 | 0.0169 (5) | 0.0179 (5) | 0.0170 (5) | −0.0012 (4) | 0.0030 (4) | −0.0019 (4) |
C10 | 0.0232 (6) | 0.0190 (6) | 0.0258 (6) | 0.0036 (5) | 0.0064 (5) | 0.0027 (5) |
C11 | 0.0249 (6) | 0.0185 (6) | 0.0251 (6) | −0.0033 (5) | 0.0096 (5) | 0.0031 (5) |
C12 | 0.0184 (5) | 0.0198 (6) | 0.0189 (5) | 0.0007 (4) | 0.0060 (4) | −0.0012 (4) |
C13 | 0.0207 (5) | 0.0190 (6) | 0.0171 (5) | −0.0008 (4) | 0.0070 (4) | −0.0022 (4) |
C14 | 0.0219 (5) | 0.0160 (5) | 0.0170 (5) | −0.0006 (4) | 0.0069 (4) | 0.0001 (4) |
C15 | 0.0206 (5) | 0.0161 (5) | 0.0192 (5) | 0.0017 (4) | 0.0069 (4) | −0.0019 (4) |
C16 | 0.0250 (6) | 0.0184 (6) | 0.0253 (6) | −0.0005 (5) | 0.0149 (5) | −0.0008 (5) |
C17 | 0.0325 (6) | 0.0166 (6) | 0.0284 (6) | 0.0030 (5) | 0.0169 (5) | 0.0034 (5) |
C18 | 0.0256 (6) | 0.0191 (6) | 0.0241 (6) | 0.0046 (5) | 0.0113 (5) | 0.0006 (5) |
C19 | 0.0246 (6) | 0.0176 (6) | 0.0273 (6) | 0.0028 (5) | 0.0095 (5) | 0.0041 (5) |
C20 | 0.0552 (9) | 0.0222 (7) | 0.0797 (12) | 0.0092 (7) | 0.0513 (9) | 0.0175 (7) |
O1—C7 | 1.2354 (14) | C9—C10 | 1.4830 (16) |
O2—C15 | 1.3669 (14) | C10—H10A | 0.9800 |
O2—C19 | 1.4277 (14) | C10—H10B | 0.9800 |
O3—C16 | 1.3627 (14) | C10—H10C | 0.9800 |
O3—C20 | 1.4326 (16) | C11—H11A | 0.9800 |
N1—C7 | 1.3950 (14) | C11—H11B | 0.9800 |
N1—N2 | 1.4072 (13) | C11—H11C | 0.9800 |
N1—C1 | 1.4206 (15) | C12—C13 | 1.4638 (16) |
N2—C9 | 1.3731 (15) | C12—H12 | 0.9500 |
N2—C11 | 1.4673 (14) | C13—C18 | 1.3876 (17) |
N3—C12 | 1.2833 (15) | C13—C14 | 1.4067 (16) |
N3—C8 | 1.3926 (14) | C14—C15 | 1.3804 (16) |
C1—C2 | 1.3883 (16) | C14—H14 | 0.9500 |
C1—C6 | 1.3933 (17) | C15—C16 | 1.4132 (16) |
C2—C3 | 1.3890 (17) | C16—C17 | 1.3851 (17) |
C2—H2 | 0.9500 | C17—C18 | 1.3946 (17) |
C3—C4 | 1.3865 (18) | C17—H17 | 0.9500 |
C3—H3 | 0.9500 | C18—H18 | 0.9500 |
C4—C5 | 1.3879 (19) | C19—H19A | 0.9800 |
C4—H4 | 0.9500 | C19—H19B | 0.9800 |
C5—C6 | 1.3839 (18) | C19—H19C | 0.9800 |
C5—H5 | 0.9500 | C20—H20A | 0.9800 |
C6—H6 | 0.9500 | C20—H20B | 0.9800 |
C7—C8 | 1.4486 (15) | C20—H20C | 0.9800 |
C8—C9 | 1.3688 (16) | ||
C15—O2—C19 | 116.78 (9) | H10B—C10—H10C | 109.5 |
C16—O3—C20 | 116.62 (10) | N2—C11—H11A | 109.5 |
C7—N1—N2 | 109.98 (9) | N2—C11—H11B | 109.5 |
C7—N1—C1 | 124.72 (10) | H11A—C11—H11B | 109.5 |
N2—N1—C1 | 119.67 (9) | N2—C11—H11C | 109.5 |
C9—N2—N1 | 106.39 (9) | H11A—C11—H11C | 109.5 |
C9—N2—C11 | 122.28 (10) | H11B—C11—H11C | 109.5 |
N1—N2—C11 | 115.93 (9) | N3—C12—C13 | 120.78 (10) |
C12—N3—C8 | 120.78 (10) | N3—C12—H12 | 119.6 |
C2—C1—C6 | 120.57 (11) | C13—C12—H12 | 119.6 |
C2—C1—N1 | 118.44 (10) | C18—C13—C14 | 119.19 (11) |
C6—C1—N1 | 120.99 (10) | C18—C13—C12 | 120.08 (10) |
C1—C2—C3 | 119.23 (11) | C14—C13—C12 | 120.71 (10) |
C1—C2—H2 | 120.4 | C15—C14—C13 | 120.15 (11) |
C3—C2—H2 | 120.4 | C15—C14—H14 | 119.9 |
C4—C3—C2 | 120.56 (11) | C13—C14—H14 | 119.9 |
C4—C3—H3 | 119.7 | O2—C15—C14 | 125.03 (10) |
C2—C3—H3 | 119.7 | O2—C15—C16 | 114.87 (10) |
C3—C4—C5 | 119.73 (11) | C14—C15—C16 | 120.10 (10) |
C3—C4—H4 | 120.1 | O3—C16—C17 | 125.23 (11) |
C5—C4—H4 | 120.1 | O3—C16—C15 | 115.00 (10) |
C6—C5—C4 | 120.37 (12) | C17—C16—C15 | 119.77 (11) |
C6—C5—H5 | 119.8 | C16—C17—C18 | 119.66 (11) |
C4—C5—H5 | 119.8 | C16—C17—H17 | 120.2 |
C5—C6—C1 | 119.50 (11) | C18—C17—H17 | 120.2 |
C5—C6—H6 | 120.2 | C13—C18—C17 | 121.05 (11) |
C1—C6—H6 | 120.2 | C13—C18—H18 | 119.5 |
O1—C7—N1 | 123.87 (10) | C17—C18—H18 | 119.5 |
O1—C7—C8 | 131.33 (10) | O2—C19—H19A | 109.5 |
N1—C7—C8 | 104.77 (9) | O2—C19—H19B | 109.5 |
C9—C8—N3 | 122.68 (10) | H19A—C19—H19B | 109.5 |
C9—C8—C7 | 107.92 (10) | O2—C19—H19C | 109.5 |
N3—C8—C7 | 129.26 (10) | H19A—C19—H19C | 109.5 |
C8—C9—N2 | 110.34 (10) | H19B—C19—H19C | 109.5 |
C8—C9—C10 | 128.36 (11) | O3—C20—H20A | 109.5 |
N2—C9—C10 | 121.31 (10) | O3—C20—H20B | 109.5 |
C9—C10—H10A | 109.5 | H20A—C20—H20B | 109.5 |
C9—C10—H10B | 109.5 | O3—C20—H20C | 109.5 |
H10A—C10—H10B | 109.5 | H20A—C20—H20C | 109.5 |
C9—C10—H10C | 109.5 | H20B—C20—H20C | 109.5 |
H10A—C10—H10C | 109.5 | ||
C7—N1—N2—C9 | −8.00 (12) | C7—C8—C9—N2 | −3.61 (13) |
C1—N1—N2—C9 | −162.78 (10) | N3—C8—C9—C10 | −8.03 (19) |
C7—N1—N2—C11 | −147.65 (10) | C7—C8—C9—C10 | 175.83 (11) |
C1—N1—N2—C11 | 57.57 (13) | N1—N2—C9—C8 | 7.08 (12) |
C7—N1—C1—C2 | 58.12 (15) | C11—N2—C9—C8 | 143.54 (11) |
N2—N1—C1—C2 | −151.03 (10) | N1—N2—C9—C10 | −172.41 (10) |
C7—N1—C1—C6 | −121.50 (12) | C11—N2—C9—C10 | −35.94 (16) |
N2—N1—C1—C6 | 29.34 (16) | C8—N3—C12—C13 | 176.26 (10) |
C6—C1—C2—C3 | −0.05 (17) | N3—C12—C13—C18 | −168.62 (11) |
N1—C1—C2—C3 | −179.68 (10) | N3—C12—C13—C14 | 9.85 (17) |
C1—C2—C3—C4 | −1.31 (18) | C18—C13—C14—C15 | 0.35 (17) |
C2—C3—C4—C5 | 1.22 (18) | C12—C13—C14—C15 | −178.13 (10) |
C3—C4—C5—C6 | 0.25 (19) | C19—O2—C15—C14 | −6.31 (16) |
C4—C5—C6—C1 | −1.59 (19) | C19—O2—C15—C16 | 174.22 (10) |
C2—C1—C6—C5 | 1.50 (18) | C13—C14—C15—O2 | −177.20 (10) |
N1—C1—C6—C5 | −178.89 (11) | C13—C14—C15—C16 | 2.23 (17) |
N2—N1—C7—O1 | −172.69 (10) | C20—O3—C16—C17 | −0.3 (2) |
C1—N1—C7—O1 | −19.46 (17) | C20—O3—C16—C15 | 178.96 (13) |
N2—N1—C7—C8 | 5.75 (12) | O2—C15—C16—O3 | −2.53 (15) |
C1—N1—C7—C8 | 158.98 (10) | C14—C15—C16—O3 | 177.98 (11) |
C12—N3—C8—C9 | 177.56 (11) | O2—C15—C16—C17 | 176.81 (11) |
C12—N3—C8—C7 | −7.18 (18) | C14—C15—C16—C17 | −2.68 (18) |
O1—C7—C8—C9 | 176.90 (12) | O3—C16—C17—C18 | 179.80 (12) |
N1—C7—C8—C9 | −1.37 (12) | C15—C16—C17—C18 | 0.52 (19) |
O1—C7—C8—N3 | 1.1 (2) | C14—C13—C18—C17 | −2.54 (18) |
N1—C7—C8—N3 | −177.18 (11) | C12—C13—C18—C17 | 175.95 (11) |
N3—C8—C9—N2 | 172.54 (10) | C16—C17—C18—C13 | 2.10 (19) |
Experimental details
Crystal data | |
Chemical formula | C20H21N3O3 |
Mr | 351.40 |
Crystal system, space group | Monoclinic, P21/c |
Temperature (K) | 100 |
a, b, c (Å) | 12.5584 (8), 10.4752 (7), 14.6002 (9) |
β (°) | 109.039 (1) |
V (Å3) | 1815.6 (2) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.09 |
Crystal size (mm) | 0.35 × 0.25 × 0.15 |
Data collection | |
Diffractometer | Bruker SMART APEX diffractometer |
Absorption correction | – |
No. of measured, independent and observed [I > 2σ(I)] reflections | 16900, 4164, 3442 |
Rint | 0.031 |
(sin θ/λ)max (Å−1) | 0.650 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.037, 0.103, 1.00 |
No. of reflections | 4164 |
No. of parameters | 239 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.23, −0.24 |
Computer programs: APEX2 (Bruker, 2009), SAINT (Bruker, 2009), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), X-SEED (Barbour, 2001), publCIF (Westrip, 2010).
Acknowledgements
We thank King Abdul Aziz University and the University of Malaya for supporting this study.
References
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4-Aminoantipyrine (4-amino-1,2-dihydro-1,5-dimethyl-2-phenyl-3H-pyrazol-3-one) possesses an aminopyrazolone unit, a feature that allows the compound to condense with aromatic aldehydes to yield Schiff bases. The Schiff base derived from the benzaldehyde homolog has nearly coplanar phenyl and pyrazoly rings (Montalvo-González & Ariza-Castolo, 2003). In the title benzaldehyde analog (Scheme I, Fig. 1), the 6-membered ring is nearly coplanar with 5-membered pyrazolyl ring [dihedral angle between the two systems 11.4 (1) °]. The phenyl ring connected to the pyrazolyl ring is aligned at 45.5 (1)°.