organic compounds
4-(3-Phenyl-3,3a,4,5-tetrahydro-2H-benzo[g]indazol-2-yl)benzenesulfonamide ethanol monosolvate
aCenter of Excellence for Advanced Materials Research (CEAMR), King Abdulaziz University, PO Box 80203, Jeddah 21589, Saudi Arabia, bChemistry Department, Faculty of Science, King Abdulaziz University, PO Box 80203, Jeddah 21589, Saudi Arabia, and cDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
*Correspondence e-mail: edward.tiekink@gmail.com
In the title compound ethanol monosolvate, C23H21N3O2S·C2H5OH, the dihydropyrazole ring is twisted about the Csp3—Csp3 bond. Nevertheless, the ring approximates a plane (r.m.s. deviation for the fitted atoms = 0.132 Å) and forms dihedral angles of 5.80 (13) and 12.29 (12)°, respectively, with the fused- and sulfonamide-benzene rings. As the dihydropyrazole C-bound phenyl group is roughly perpendicular to the dihydropyrazole ring [dihedral angle = 74.04 (15)°; the amino group is orientated to the same side of the molecule], to a first approximation, the molecule has a stunted T-shape. The cyclohexene ring adopts a half-chair conformation with the methylene C atom connected to the dihydropyrazole ring lying 0.665 (4) Å out of the plane of the five remaining atoms (r.m.s. deviation = 0.050 Å). The components of the are connected by an O—H⋯O hydrogen bond. Further links between molecules leading to a three-dimensional architecture are of the type N—H⋯O.
Related literature
For a previous synthesis, see: Faidallah & Makki (1994). For the biological activity of related compounds, see: Faidallah et al. (2011). For the structure of the methyl analogue, see: Asiri et al. (2011).
Experimental
Crystal data
|
Refinement
|
Data collection: CrysAlis PRO (Agilent, 2012); cell CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997) and DIAMOND (Brandenburg, 2006); software used to prepare material for publication: publCIF (Westrip, 2010).
Supporting information
https://doi.org/10.1107/S1600536812028474/xu5573sup1.cif
contains datablocks global, I. DOI:Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536812028474/xu5573Isup2.hkl
Supporting information file. DOI: https://doi.org/10.1107/S1600536812028474/xu5573Isup3.cml
A solution of 2-benzylidene-3,4-dihydro-2H-naphthalen-1-one (2.3 g, 0.01 M) in ethanol (50 ml) was refluxed with 4-hydrazinobenzenesulfonamide hydrochloride (2.2 g, 0.01 M) for 4 h. The reaction mixture was allowed to cool. The formed precipitate was filtered, washed with water, dried and recrystallized from ethanol. M.pt: 508–510 K cf. Lit. M.pt: 508 K (Faidallah & Makki, 1994). Yield: 70%.
Carbon-bound H-atoms were placed in calculated positions [C—H = 0.95–1.00 Å, Uiso(H) = 1.2–1.5Ueq(C)] and were included in the
in the riding model approximation. The oxygen- and nitrogen-bound H-atom were located in a difference Fourier map and was refined with a distance restraints of O—H = 0.84±0.01 Å and N—H = 0.88±0.01 Å; the Uiso values were refined.The title compound, (I), reported previously in the literature (Faidallah & Makki, 1994), comprises a benzenesulfonamide unit which is grafted to a chemotherapeutic heterocycle pyrazole derivative, and therefore is a compound which is anticipated to exhibit enhanced activities (Faidallah et al., 2011).
In (I), Fig. 1, pyrazole ring is twisted about the C10—C11 bond (r.m.s. deviation for the fitted atoms = 0.132 Å). The cyclohexene ring adopts a half-chair conformation with the C9 atom lying 0.665 (4) Å out of the plane of the five remaining atoms (r.m.s. deviation = 0.050 Å). The fused-ring- and sulfonamide-benzene rings form dihedral angles of 5.80 (13) and 12.29 (12)°, respectively, with the least-squares plane through the pyrazole ring. By contrast, the pyrazole-C-bound phenyl group is almost perpendicular to the pyrazole ring, forming a dihedral angle of 74.04 (15)°, so that to a first approximation, the molecule has a stunted T-shape. The sulfonamide-amino group is orientated to the same side of the molecule as the pyrazole-C-bound benzene ring. While the sulfonamide-O1 atom is almost co-planar with the benzene ring, the O1—S1—C21—C20 torsion angle is -168.51 (17)°, the O2 atom is somewhat splayed [O2—S1—C21—C20 = -38.9 (2)°]. In the structure of the compound where the pyrazole-C-bound substituent is methyl rather than phenyl, the molecule has a shallow bowl-shaped conformation (Asiri et al., 2011).
The
comprises the organic molecule and a ethanol molecule of solvation with the primary connection between them being a O—H···O hydrogen bond, Table 1. Each amino-H forms a hydrogen bond to an oxygen atom so that each oxygen atom in the structure functions as an acceptor, Table 1, and that a three-dimensional architecture results, Fig. 2.For a previous synthesis, see: Faidallah & Makki (1994). For the biological activity of related compounds, see: Faidallah et al. (2011). For the structure of the methyl analogue, see: Asiri et al. (2011).
Data collection: CrysAlis PRO (Agilent, 2012); cell
CrysAlis PRO (Agilent, 2012); data reduction: CrysAlis PRO (Agilent, 2012); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997) and DIAMOND (Brandenburg, 2006); software used to prepare material for publication: publCIF (Westrip, 2010).C23H21N3O2S·C2H6O | F(000) = 952 |
Mr = 449.56 | Dx = 1.327 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2yn | Cell parameters from 4495 reflections |
a = 15.7556 (9) Å | θ = 2.5–27.5° |
b = 9.1789 (4) Å | µ = 0.18 mm−1 |
c = 16.7515 (10) Å | T = 100 K |
β = 111.718 (7)° | Prsim, light-brown |
V = 2250.6 (2) Å3 | 0.30 × 0.25 × 0.20 mm |
Z = 4 |
Agilent SuperNova Dual diffractometer with an Atlas detector | 5196 independent reflections |
Radiation source: SuperNova (Mo) X-ray Source | 3971 reflections with I > 2σ(I) |
Mirror monochromator | Rint = 0.036 |
Detector resolution: 10.4041 pixels mm-1 | θmax = 27.6°, θmin = 2.6° |
ω scan | h = −20→16 |
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2012) | k = −11→11 |
Tmin = 0.761, Tmax = 1.000 | l = −17→21 |
15054 measured reflections |
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)] = 0.054 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.156 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.04 | w = 1/[σ2(Fo2) + (0.0701P)2 + 1.7118P] where P = (Fo2 + 2Fc2)/3 |
5196 reflections | (Δ/σ)max = 0.001 |
301 parameters | Δρmax = 0.81 e Å−3 |
3 restraints | Δρmin = −0.45 e Å−3 |
C23H21N3O2S·C2H6O | V = 2250.6 (2) Å3 |
Mr = 449.56 | Z = 4 |
Monoclinic, P21/n | Mo Kα radiation |
a = 15.7556 (9) Å | µ = 0.18 mm−1 |
b = 9.1789 (4) Å | T = 100 K |
c = 16.7515 (10) Å | 0.30 × 0.25 × 0.20 mm |
β = 111.718 (7)° |
Agilent SuperNova Dual diffractometer with an Atlas detector | 5196 independent reflections |
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2012) | 3971 reflections with I > 2σ(I) |
Tmin = 0.761, Tmax = 1.000 | Rint = 0.036 |
15054 measured reflections |
R[F2 > 2σ(F2)] = 0.054 | 3 restraints |
wR(F2) = 0.156 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.04 | Δρmax = 0.81 e Å−3 |
5196 reflections | Δρmin = −0.45 e Å−3 |
301 parameters |
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 | Uiso*/Ueq | ||
S1 | 0.56232 (4) | 0.84182 (6) | 0.60754 (4) | 0.02401 (16) | |
O1 | 0.62832 (11) | 0.73972 (19) | 0.66013 (11) | 0.0328 (4) | |
O2 | 0.52421 (11) | 0.82084 (18) | 0.51577 (10) | 0.0295 (4) | |
O3 | 0.78024 (13) | 0.5436 (2) | 0.69624 (13) | 0.0455 (5) | |
N1 | 0.17020 (12) | 0.91470 (19) | 0.67783 (11) | 0.0199 (4) | |
N2 | 0.25282 (13) | 0.8494 (2) | 0.72722 (12) | 0.0251 (4) | |
N3 | 0.61120 (13) | 0.9993 (2) | 0.62362 (14) | 0.0275 (4) | |
C1 | 0.11176 (15) | 0.8807 (3) | 0.71164 (14) | 0.0243 (5) | |
C2 | 0.01730 (15) | 0.9315 (2) | 0.68075 (14) | 0.0220 (5) | |
C3 | −0.02015 (15) | 1.0140 (2) | 0.60582 (14) | 0.0235 (5) | |
H3 | 0.0168 | 1.0402 | 0.5743 | 0.028* | |
C4 | −0.10982 (16) | 1.0577 (3) | 0.57728 (16) | 0.0283 (5) | |
H4 | −0.1348 | 1.1142 | 0.5264 | 0.034* | |
C5 | −0.16410 (16) | 1.0184 (3) | 0.62350 (17) | 0.0315 (5) | |
H5 | −0.2264 | 1.0472 | 0.6037 | 0.038* | |
C6 | −0.12745 (17) | 0.9380 (3) | 0.69772 (17) | 0.0310 (5) | |
H6 | −0.1652 | 0.9116 | 0.7284 | 0.037* | |
C7 | −0.03598 (16) | 0.8944 (3) | 0.72900 (16) | 0.0272 (5) | |
C8 | 0.00372 (18) | 0.8092 (3) | 0.81182 (17) | 0.0358 (6) | |
H8A | −0.0152 | 0.7060 | 0.8002 | 0.043* | |
H8B | −0.0223 | 0.8472 | 0.8532 | 0.043* | |
C9 | 0.10743 (18) | 0.8158 (3) | 0.85304 (17) | 0.0360 (6) | |
H9A | 0.1270 | 0.9154 | 0.8749 | 0.043* | |
H9B | 0.1295 | 0.7473 | 0.9021 | 0.043* | |
C10 | 0.14749 (17) | 0.7754 (3) | 0.78660 (16) | 0.0302 (5) | |
H10 | 0.1262 | 0.6752 | 0.7650 | 0.036* | |
C11 | 0.25155 (16) | 0.7839 (3) | 0.80769 (15) | 0.0262 (5) | |
H11 | 0.2768 | 0.6828 | 0.8135 | 0.031* | |
C12 | 0.30768 (16) | 0.8718 (2) | 0.88630 (15) | 0.0263 (5) | |
C13 | 0.3217 (2) | 1.0205 (3) | 0.88187 (17) | 0.0360 (6) | |
H13 | 0.2957 | 1.0694 | 0.8283 | 0.043* | |
C14 | 0.3723 (2) | 1.0976 (3) | 0.95360 (19) | 0.0465 (7) | |
H14 | 0.3820 | 1.1990 | 0.9492 | 0.056* | |
C15 | 0.4096 (2) | 1.0290 (3) | 1.0325 (2) | 0.0509 (8) | |
H15 | 0.4447 | 1.0828 | 1.0822 | 0.061* | |
C16 | 0.3952 (2) | 0.8806 (3) | 1.03832 (19) | 0.0480 (7) | |
H16 | 0.4194 | 0.8330 | 1.0924 | 0.058* | |
C17 | 0.34566 (19) | 0.8023 (3) | 0.96556 (17) | 0.0363 (6) | |
H17 | 0.3375 | 0.7004 | 0.9696 | 0.044* | |
C18 | 0.32543 (14) | 0.8521 (2) | 0.70087 (14) | 0.0192 (4) | |
C19 | 0.31803 (14) | 0.9196 (2) | 0.62303 (14) | 0.0208 (4) | |
H19 | 0.2631 | 0.9679 | 0.5895 | 0.025* | |
C20 | 0.39002 (15) | 0.9158 (2) | 0.59542 (14) | 0.0223 (5) | |
H20 | 0.3844 | 0.9610 | 0.5427 | 0.027* | |
C21 | 0.47139 (14) | 0.8456 (2) | 0.64448 (14) | 0.0210 (4) | |
C22 | 0.48012 (15) | 0.7814 (2) | 0.72190 (15) | 0.0236 (5) | |
H22 | 0.5356 | 0.7347 | 0.7556 | 0.028* | |
C23 | 0.40790 (15) | 0.7853 (2) | 0.75024 (14) | 0.0236 (5) | |
H23 | 0.4145 | 0.7420 | 0.8037 | 0.028* | |
C24 | 0.7520 (3) | 0.4101 (4) | 0.6419 (2) | 0.0558 (8) | |
H24A | 0.8069 | 0.3642 | 0.6373 | 0.067* | |
H24B | 0.7250 | 0.3397 | 0.6706 | 0.067* | |
C25 | 0.6861 (3) | 0.4394 (4) | 0.5558 (3) | 0.0666 (10) | |
H25A | 0.6701 | 0.3481 | 0.5234 | 0.100* | |
H25B | 0.7128 | 0.5071 | 0.5264 | 0.100* | |
H25C | 0.6309 | 0.4829 | 0.5597 | 0.100* | |
H1n | 0.6416 (19) | 1.014 (4) | 0.6783 (8) | 0.054 (10)* | |
H2n | 0.5739 (14) | 1.066 (2) | 0.5919 (14) | 0.028 (7)* | |
H3o | 0.7383 (16) | 0.605 (3) | 0.687 (2) | 0.054 (10)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
S1 | 0.0220 (3) | 0.0289 (3) | 0.0241 (3) | 0.0055 (2) | 0.0119 (2) | −0.0008 (2) |
O1 | 0.0288 (9) | 0.0381 (9) | 0.0339 (10) | 0.0136 (7) | 0.0143 (8) | 0.0045 (8) |
O2 | 0.0310 (9) | 0.0369 (9) | 0.0238 (9) | 0.0034 (7) | 0.0139 (7) | −0.0061 (7) |
O3 | 0.0360 (10) | 0.0508 (12) | 0.0452 (12) | 0.0167 (9) | 0.0099 (9) | 0.0101 (10) |
N1 | 0.0223 (9) | 0.0203 (9) | 0.0189 (9) | −0.0011 (7) | 0.0099 (8) | −0.0027 (7) |
N2 | 0.0226 (9) | 0.0339 (10) | 0.0204 (10) | 0.0037 (8) | 0.0099 (8) | 0.0090 (8) |
N3 | 0.0221 (10) | 0.0343 (11) | 0.0283 (12) | 0.0009 (9) | 0.0119 (9) | 0.0002 (9) |
C1 | 0.0266 (11) | 0.0293 (11) | 0.0203 (11) | −0.0045 (9) | 0.0125 (9) | −0.0027 (9) |
C2 | 0.0235 (11) | 0.0227 (10) | 0.0236 (11) | −0.0061 (9) | 0.0131 (9) | −0.0055 (9) |
C3 | 0.0234 (10) | 0.0259 (11) | 0.0237 (12) | −0.0062 (9) | 0.0115 (9) | −0.0047 (9) |
C4 | 0.0258 (11) | 0.0299 (12) | 0.0283 (13) | −0.0035 (10) | 0.0088 (10) | −0.0022 (10) |
C5 | 0.0230 (11) | 0.0333 (12) | 0.0415 (15) | −0.0031 (10) | 0.0155 (11) | −0.0056 (11) |
C6 | 0.0302 (12) | 0.0310 (12) | 0.0409 (15) | −0.0044 (10) | 0.0236 (12) | −0.0030 (11) |
C7 | 0.0313 (12) | 0.0257 (11) | 0.0318 (13) | −0.0033 (10) | 0.0201 (11) | −0.0033 (10) |
C8 | 0.0378 (14) | 0.0435 (14) | 0.0380 (15) | 0.0015 (12) | 0.0276 (13) | 0.0073 (12) |
C9 | 0.0399 (14) | 0.0433 (14) | 0.0336 (14) | 0.0112 (12) | 0.0239 (12) | 0.0132 (12) |
C10 | 0.0352 (13) | 0.0294 (12) | 0.0313 (13) | 0.0011 (10) | 0.0187 (11) | 0.0038 (10) |
C11 | 0.0290 (12) | 0.0305 (11) | 0.0229 (12) | 0.0030 (10) | 0.0141 (10) | 0.0065 (9) |
C12 | 0.0333 (12) | 0.0255 (11) | 0.0243 (12) | 0.0089 (10) | 0.0158 (10) | 0.0044 (9) |
C13 | 0.0557 (17) | 0.0276 (12) | 0.0300 (14) | 0.0099 (12) | 0.0220 (13) | 0.0045 (10) |
C14 | 0.071 (2) | 0.0300 (13) | 0.0424 (17) | −0.0030 (14) | 0.0262 (16) | −0.0046 (12) |
C15 | 0.068 (2) | 0.0465 (17) | 0.0341 (16) | −0.0026 (15) | 0.0144 (15) | −0.0128 (13) |
C16 | 0.064 (2) | 0.0488 (17) | 0.0250 (14) | 0.0069 (15) | 0.0094 (14) | 0.0021 (12) |
C17 | 0.0504 (16) | 0.0290 (12) | 0.0283 (13) | 0.0059 (12) | 0.0132 (12) | 0.0062 (10) |
C18 | 0.0219 (10) | 0.0179 (10) | 0.0195 (11) | −0.0021 (8) | 0.0095 (9) | −0.0024 (8) |
C19 | 0.0193 (10) | 0.0249 (11) | 0.0171 (11) | 0.0006 (8) | 0.0056 (9) | 0.0003 (8) |
C20 | 0.0234 (11) | 0.0264 (11) | 0.0182 (11) | 0.0006 (9) | 0.0088 (9) | 0.0012 (9) |
C21 | 0.0207 (10) | 0.0217 (10) | 0.0215 (11) | 0.0011 (8) | 0.0090 (9) | −0.0030 (8) |
C22 | 0.0228 (10) | 0.0220 (10) | 0.0256 (12) | 0.0038 (9) | 0.0083 (9) | 0.0023 (9) |
C23 | 0.0265 (11) | 0.0246 (11) | 0.0204 (11) | 0.0040 (9) | 0.0095 (9) | 0.0048 (9) |
C24 | 0.071 (2) | 0.0537 (19) | 0.052 (2) | 0.0154 (17) | 0.0332 (18) | −0.0003 (15) |
C25 | 0.067 (2) | 0.071 (2) | 0.064 (3) | −0.0048 (19) | 0.027 (2) | −0.0164 (19) |
S1—O1 | 1.4345 (17) | C10—C11 | 1.546 (3) |
S1—O2 | 1.4414 (17) | C10—H10 | 1.0000 |
S1—N3 | 1.613 (2) | C11—C12 | 1.518 (3) |
S1—C21 | 1.759 (2) | C11—H11 | 1.0000 |
O3—C24 | 1.493 (4) | C12—C17 | 1.393 (3) |
O3—H3o | 0.839 (10) | C12—C13 | 1.389 (3) |
N1—C1 | 1.285 (3) | C13—C14 | 1.368 (4) |
N1—N2 | 1.393 (3) | C13—H13 | 0.9500 |
N2—C18 | 1.370 (3) | C14—C15 | 1.384 (4) |
N2—C11 | 1.483 (3) | C14—H14 | 0.9500 |
N3—H1n | 0.873 (10) | C15—C16 | 1.390 (4) |
N3—H2n | 0.877 (10) | C15—H15 | 0.9500 |
C1—C2 | 1.459 (3) | C16—C17 | 1.381 (4) |
C1—C10 | 1.518 (3) | C16—H16 | 0.9500 |
C2—C3 | 1.396 (3) | C17—H17 | 0.9500 |
C2—C7 | 1.406 (3) | C18—C23 | 1.398 (3) |
C3—C4 | 1.373 (3) | C18—C19 | 1.409 (3) |
C3—H3 | 0.9500 | C19—C20 | 1.375 (3) |
C4—C5 | 1.397 (3) | C19—H19 | 0.9500 |
C4—H4 | 0.9500 | C20—C21 | 1.398 (3) |
C5—C6 | 1.375 (4) | C20—H20 | 0.9500 |
C5—H5 | 0.9500 | C21—C22 | 1.384 (3) |
C6—C7 | 1.398 (3) | C22—C23 | 1.386 (3) |
C6—H6 | 0.9500 | C22—H22 | 0.9500 |
C7—C8 | 1.512 (3) | C23—H23 | 0.9500 |
C8—C9 | 1.522 (4) | C24—C25 | 1.457 (5) |
C8—H8A | 0.9900 | C24—H24A | 0.9900 |
C8—H8B | 0.9900 | C24—H24B | 0.9900 |
C9—C10 | 1.515 (3) | C25—H25A | 0.9800 |
C9—H9A | 0.9900 | C25—H25B | 0.9800 |
C9—H9B | 0.9900 | C25—H25C | 0.9800 |
O1—S1—O2 | 119.27 (10) | N2—C11—C10 | 100.52 (18) |
O1—S1—N3 | 106.86 (11) | C12—C11—C10 | 116.95 (19) |
O2—S1—N3 | 106.42 (11) | N2—C11—H11 | 109.0 |
O1—S1—C21 | 107.25 (10) | C12—C11—H11 | 109.0 |
O2—S1—C21 | 107.81 (10) | C10—C11—H11 | 109.0 |
N3—S1—C21 | 108.93 (10) | C17—C12—C13 | 118.7 (2) |
C24—O3—H3o | 114 (2) | C17—C12—C11 | 119.3 (2) |
C1—N1—N2 | 107.35 (18) | C13—C12—C11 | 121.9 (2) |
C18—N2—N1 | 120.57 (17) | C14—C13—C12 | 120.9 (2) |
C18—N2—C11 | 126.45 (18) | C14—C13—H13 | 119.5 |
N1—N2—C11 | 112.97 (16) | C12—C13—H13 | 119.5 |
S1—N3—H1n | 111 (2) | C13—C14—C15 | 120.5 (3) |
S1—N3—H2n | 110.5 (17) | C13—C14—H14 | 119.8 |
H1n—N3—H2n | 121 (3) | C15—C14—H14 | 119.8 |
N1—C1—C2 | 124.7 (2) | C14—C15—C16 | 119.4 (3) |
N1—C1—C10 | 114.3 (2) | C14—C15—H15 | 120.3 |
C2—C1—C10 | 120.91 (19) | C16—C15—H15 | 120.3 |
C3—C2—C7 | 120.3 (2) | C17—C16—C15 | 120.1 (3) |
C3—C2—C1 | 121.89 (19) | C17—C16—H16 | 119.9 |
C7—C2—C1 | 117.8 (2) | C15—C16—H16 | 119.9 |
C4—C3—C2 | 120.6 (2) | C16—C17—C12 | 120.4 (3) |
C4—C3—H3 | 119.7 | C16—C17—H17 | 119.8 |
C2—C3—H3 | 119.7 | C12—C17—H17 | 119.8 |
C3—C4—C5 | 119.6 (2) | N2—C18—C23 | 120.35 (19) |
C3—C4—H4 | 120.2 | N2—C18—C19 | 120.88 (19) |
C5—C4—H4 | 120.2 | C23—C18—C19 | 118.76 (19) |
C6—C5—C4 | 120.1 (2) | C20—C19—C18 | 120.3 (2) |
C6—C5—H5 | 120.0 | C20—C19—H19 | 119.9 |
C4—C5—H5 | 120.0 | C18—C19—H19 | 119.9 |
C5—C6—C7 | 121.5 (2) | C19—C20—C21 | 120.4 (2) |
C5—C6—H6 | 119.3 | C19—C20—H20 | 119.8 |
C7—C6—H6 | 119.3 | C21—C20—H20 | 119.8 |
C6—C7—C2 | 117.9 (2) | C22—C21—C20 | 119.90 (19) |
C6—C7—C8 | 120.8 (2) | C22—C21—S1 | 120.66 (17) |
C2—C7—C8 | 121.4 (2) | C20—C21—S1 | 119.44 (16) |
C7—C8—C9 | 113.95 (19) | C21—C22—C23 | 120.0 (2) |
C7—C8—H8A | 108.8 | C21—C22—H22 | 120.0 |
C9—C8—H8A | 108.8 | C23—C22—H22 | 120.0 |
C7—C8—H8B | 108.8 | C22—C23—C18 | 120.6 (2) |
C9—C8—H8B | 108.8 | C22—C23—H23 | 119.7 |
H8A—C8—H8B | 107.7 | C18—C23—H23 | 119.7 |
C10—C9—C8 | 109.0 (2) | C25—C24—O3 | 113.2 (3) |
C10—C9—H9A | 109.9 | C25—C24—H24A | 108.9 |
C8—C9—H9A | 109.9 | O3—C24—H24A | 108.9 |
C10—C9—H9B | 109.9 | C25—C24—H24B | 108.9 |
C8—C9—H9B | 109.9 | O3—C24—H24B | 108.9 |
H9A—C9—H9B | 108.3 | H24A—C24—H24B | 107.7 |
C9—C10—C1 | 108.90 (19) | C24—C25—H25A | 109.5 |
C9—C10—C11 | 121.0 (2) | C24—C25—H25B | 109.5 |
C1—C10—C11 | 101.19 (17) | H25A—C25—H25B | 109.5 |
C9—C10—H10 | 108.4 | C24—C25—H25C | 109.5 |
C1—C10—H10 | 108.4 | H25A—C25—H25C | 109.5 |
C11—C10—H10 | 108.4 | H25B—C25—H25C | 109.5 |
N2—C11—C12 | 111.94 (19) | ||
C1—N1—N2—C18 | 172.3 (2) | C9—C10—C11—C12 | −16.4 (3) |
C1—N1—N2—C11 | −8.9 (2) | C1—C10—C11—C12 | 103.9 (2) |
N2—N1—C1—C2 | 177.9 (2) | N2—C11—C12—C17 | −153.5 (2) |
N2—N1—C1—C10 | −4.5 (3) | C10—C11—C12—C17 | 91.3 (3) |
N1—C1—C2—C3 | 5.3 (3) | N2—C11—C12—C13 | 27.2 (3) |
C10—C1—C2—C3 | −172.2 (2) | C10—C11—C12—C13 | −88.0 (3) |
N1—C1—C2—C7 | −174.8 (2) | C17—C12—C13—C14 | 0.5 (4) |
C10—C1—C2—C7 | 7.8 (3) | C11—C12—C13—C14 | 179.8 (2) |
C7—C2—C3—C4 | −1.3 (3) | C12—C13—C14—C15 | −1.0 (4) |
C1—C2—C3—C4 | 178.6 (2) | C13—C14—C15—C16 | 0.1 (5) |
C2—C3—C4—C5 | −0.3 (3) | C14—C15—C16—C17 | 1.3 (5) |
C3—C4—C5—C6 | 0.8 (4) | C15—C16—C17—C12 | −1.8 (5) |
C4—C5—C6—C7 | 0.3 (4) | C13—C12—C17—C16 | 0.9 (4) |
C5—C6—C7—C2 | −1.9 (4) | C11—C12—C17—C16 | −178.5 (2) |
C5—C6—C7—C8 | 178.5 (2) | N1—N2—C18—C23 | −179.40 (19) |
C3—C2—C7—C6 | 2.3 (3) | C11—N2—C18—C23 | 2.0 (3) |
C1—C2—C7—C6 | −177.6 (2) | N1—N2—C18—C19 | −0.6 (3) |
C3—C2—C7—C8 | −178.0 (2) | C11—N2—C18—C19 | −179.3 (2) |
C1—C2—C7—C8 | 2.1 (3) | N2—C18—C19—C20 | −177.0 (2) |
C6—C7—C8—C9 | −159.6 (2) | C23—C18—C19—C20 | 1.8 (3) |
C2—C7—C8—C9 | 20.8 (3) | C18—C19—C20—C21 | −0.3 (3) |
C7—C8—C9—C10 | −51.6 (3) | C19—C20—C21—C22 | −0.9 (3) |
C8—C9—C10—C1 | 58.8 (3) | C19—C20—C21—S1 | 179.81 (17) |
C8—C9—C10—C11 | 175.3 (2) | O1—S1—C21—C22 | 12.3 (2) |
N1—C1—C10—C9 | 143.4 (2) | O2—S1—C21—C22 | 141.86 (18) |
C2—C1—C10—C9 | −38.9 (3) | N3—S1—C21—C22 | −103.05 (19) |
N1—C1—C10—C11 | 14.9 (3) | O1—S1—C21—C20 | −168.51 (17) |
C2—C1—C10—C11 | −167.4 (2) | O2—S1—C21—C20 | −38.9 (2) |
C18—N2—C11—C12 | 71.2 (3) | N3—S1—C21—C20 | 76.2 (2) |
N1—N2—C11—C12 | −107.5 (2) | C20—C21—C22—C23 | 0.7 (3) |
C18—N2—C11—C10 | −163.9 (2) | S1—C21—C22—C23 | 179.98 (17) |
N1—N2—C11—C10 | 17.4 (2) | C21—C22—C23—C18 | 0.7 (3) |
C9—C10—C11—N2 | −137.8 (2) | N2—C18—C23—C22 | 176.8 (2) |
C1—C10—C11—N2 | −17.5 (2) | C19—C18—C23—C22 | −2.0 (3) |
D—H···A | D—H | H···A | D···A | D—H···A |
O3—H3o···O1 | 0.84 (1) | 2.04 (1) | 2.875 (2) | 175 (3) |
N3—H1n···O3i | 0.87 (1) | 2.02 (1) | 2.894 (3) | 176 (3) |
N3—H2n···O2ii | 0.88 (1) | 2.16 (1) | 3.007 (3) | 163 (2) |
Symmetry codes: (i) −x+3/2, y+1/2, −z+3/2; (ii) −x+1, −y+2, −z+1. |
Experimental details
Crystal data | |
Chemical formula | C23H21N3O2S·C2H6O |
Mr | 449.56 |
Crystal system, space group | Monoclinic, P21/n |
Temperature (K) | 100 |
a, b, c (Å) | 15.7556 (9), 9.1789 (4), 16.7515 (10) |
β (°) | 111.718 (7) |
V (Å3) | 2250.6 (2) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.18 |
Crystal size (mm) | 0.30 × 0.25 × 0.20 |
Data collection | |
Diffractometer | Agilent SuperNova Dual diffractometer with an Atlas detector |
Absorption correction | Multi-scan (CrysAlis PRO; Agilent, 2012) |
Tmin, Tmax | 0.761, 1.000 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 15054, 5196, 3971 |
Rint | 0.036 |
(sin θ/λ)max (Å−1) | 0.651 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.054, 0.156, 1.04 |
No. of reflections | 5196 |
No. of parameters | 301 |
No. of restraints | 3 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.81, −0.45 |
Computer programs: CrysAlis PRO (Agilent, 2012), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997) and DIAMOND (Brandenburg, 2006), publCIF (Westrip, 2010).
D—H···A | D—H | H···A | D···A | D—H···A |
O3—H3o···O1 | 0.839 (10) | 2.038 (11) | 2.875 (2) | 175 (3) |
N3—H1n···O3i | 0.873 (10) | 2.022 (11) | 2.894 (3) | 176 (3) |
N3—H2n···O2ii | 0.877 (10) | 2.160 (13) | 3.007 (3) | 163 (2) |
Symmetry codes: (i) −x+3/2, y+1/2, −z+3/2; (ii) −x+1, −y+2, −z+1. |
Footnotes
‡Additional correspondence author, e-mail: aasiri2@kau.edu.sa.
Acknowledgements
The authors are grateful to King Abdulaziz University for providing research facilities. We also thank the Ministry of Higher Education (Malaysia) for funding structural studies through the High-Impact Research scheme (UM.C/HIR/MOHE/SC/12).
References
Agilent (2012). CrysAlis PRO. Agilent Technologies, Yarnton, England. Google Scholar
Asiri, A. M., Faidallah, H. M., Al-Youbi, A. O., Makki, M. S. I. T. & Ng, S. W. (2011). Acta Cryst. E67, o2441. Web of Science CSD CrossRef IUCr Journals Google Scholar
Brandenburg, K. (2006). DIAMOND. Crystal Impact GbR, Bonn, Germany. Google Scholar
Faidallah, H. M., Khan, K. A. & Asiri, A. M. (2011). J. Fluorine Chem. 132, 131–137. Web of Science CrossRef CAS Google Scholar
Faidallah, H. M. & Makki, M. S. I. (1994). J. Chin. Chem. Soc. 41, 585–589. CAS Google Scholar
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. CrossRef IUCr Journals Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920–925. Web of Science CrossRef CAS IUCr Journals Google Scholar
This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.
The title compound, (I), reported previously in the literature (Faidallah & Makki, 1994), comprises a benzenesulfonamide unit which is grafted to a chemotherapeutic heterocycle pyrazole derivative, and therefore is a compound which is anticipated to exhibit enhanced activities (Faidallah et al., 2011).
In (I), Fig. 1, pyrazole ring is twisted about the C10—C11 bond (r.m.s. deviation for the fitted atoms = 0.132 Å). The cyclohexene ring adopts a half-chair conformation with the C9 atom lying 0.665 (4) Å out of the plane of the five remaining atoms (r.m.s. deviation = 0.050 Å). The fused-ring- and sulfonamide-benzene rings form dihedral angles of 5.80 (13) and 12.29 (12)°, respectively, with the least-squares plane through the pyrazole ring. By contrast, the pyrazole-C-bound phenyl group is almost perpendicular to the pyrazole ring, forming a dihedral angle of 74.04 (15)°, so that to a first approximation, the molecule has a stunted T-shape. The sulfonamide-amino group is orientated to the same side of the molecule as the pyrazole-C-bound benzene ring. While the sulfonamide-O1 atom is almost co-planar with the benzene ring, the O1—S1—C21—C20 torsion angle is -168.51 (17)°, the O2 atom is somewhat splayed [O2—S1—C21—C20 = -38.9 (2)°]. In the structure of the compound where the pyrazole-C-bound substituent is methyl rather than phenyl, the molecule has a shallow bowl-shaped conformation (Asiri et al., 2011).
The asymmetric unit comprises the organic molecule and a ethanol molecule of solvation with the primary connection between them being a O—H···O hydrogen bond, Table 1. Each amino-H forms a hydrogen bond to an oxygen atom so that each oxygen atom in the structure functions as an acceptor, Table 1, and that a three-dimensional architecture results, Fig. 2.