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The structures of two arylsulfonamide
para-alkoxychalcones, namely,
N-{4-[(
E)-3-(4-methoxyphenyl)prop-2-enoyl]phenyl}benzenesulfonamide, C
22H
19NO
4S, (I), and
N-{4-[(
E)-3-(4-ethoxyphenyl)prop-2-enoyl]phenyl}benzenesulfonamide, C
23H
21NO
4S, (II), reveal the effect of the inclusion of one -CH
2- group between the CH
3 branch and the alkoxy O atom on the conformation and crystal structure. Although the molecular conformations and one-dimensional chain motifs are the same in both structures, their crystallographic symmetry, number of independent molecules and crystal packing are different. The crystal packing of (I) is stabilized by weak C-H
and
-
interactions, while only C-H
contacts occur in the structure of (II). The role of the additional methylene group in the crystal packing can also be seen in the fact that the alkoxy O atom is an acceptor in nonclassical hydrogen bonds only in the
para-ethoxy analogue, (II). The remarkable similarity between the crystal packing features of (I) and (II) lies in the formation of N-H
O hydrogen-bonded ribbons, a synthon commonly found in related compounds.
Supporting information
CCDC references: 934567; 934568
Compounds (I) and (II) were synthesized by Claisen–Schmidt condensation from
N-(4-acetylphenyl)benzenesulfonamide with either
p-methoxybenzene [compound (I)] or p-etoxybenzaldehyde [compound
(II)], using sodium hydroxide in ethanol (50% w/w) as catalyst.
The reactions were performed at 343 K for about either 22 [compound (I)] or 24
[compound (II)] h. In each case, the precipitate was re-crystallized from
suitable solvents [Which solvent for each?] to obtain single crystals.
The reaction yields were 57 and 65% for (I) and (II), respectively. Their
melting point ranges were 446–448 K and 425–427 K, respectively.
All C-bound H atoms were placed geometrically and refined using a riding model,
with C—H = 0.97 (CH2), 0.96 (CH3) or 0.93 Å (aromatic groups), and
with Uiso(H) = 1.2Ueq(C). Atom H1 bonded to N was found in a
difference Fourier map and its positional parameters were refined freely;
Uiso(H) = 1.2Ueq(N)
For both compounds, data collection: COLLECT (Nonius, 2000); cell refinement: HKL SCALEPACK (Otwinowski & Minor, 1997); data reduction: HKL DENZO and SCALEPACK (Otwinowski & Minor, 1997); program(s) used to solve structure: SIR92 (Altomare et al., 1993); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997) and Mercury (Macrae et al., 2008); software used to prepare material for publication: WinGX (Farrugia, 1999).
(I)
N-{4-[(
E)-3-(4-Methoxyphenyl)prop-2-enoyl]phenyl}benzenesulfonamide
top
Crystal data top
C22H19NO4S | Z = 4 |
Mr = 393.44 | F(000) = 824 |
Triclinic, P1 | Dx = 1.341 Mg m−3 |
Hall symbol: -P1 | Mo Kα radiation, λ = 0.71073 Å |
a = 11.8650 (3) Å | Cell parameters from 6621 reflections |
b = 12.2420 (3) Å | θ = 2.4–22.8° |
c = 14.7287 (3) Å | µ = 0.19 mm−1 |
α = 68.075 (1)° | T = 298 K |
β = 81.665 (1)° | Prism, yellow |
γ = 80.437 (1)° | 0.28 × 0.15 × 0.08 mm |
V = 1948.99 (8) Å3 | |
Data collection top
Nonius KappaCCD area-detector diffractometer | 5268 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.039 |
Detector resolution: 9 pixels mm-1 | θmax = 26.9°, θmin = 1.5° |
CCD scans | h = −15→14 |
22723 measured reflections | k = −14→15 |
8378 independent reflections | l = −18→17 |
Refinement top
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) = 0.152 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.02 | w = 1/[σ2(Fo2) + (0.0555P)2 + 0.7349P] where P = (Fo2 + 2Fc2)/3 |
8378 reflections | (Δ/σ)max < 0.001 |
512 parameters | Δρmax = 0.24 e Å−3 |
0 restraints | Δρmin = −0.27 e Å−3 |
Crystal data top
C22H19NO4S | γ = 80.437 (1)° |
Mr = 393.44 | V = 1948.99 (8) Å3 |
Triclinic, P1 | Z = 4 |
a = 11.8650 (3) Å | Mo Kα radiation |
b = 12.2420 (3) Å | µ = 0.19 mm−1 |
c = 14.7287 (3) Å | T = 298 K |
α = 68.075 (1)° | 0.28 × 0.15 × 0.08 mm |
β = 81.665 (1)° | |
Data collection top
Nonius KappaCCD area-detector diffractometer | 5268 reflections with I > 2σ(I) |
22723 measured reflections | Rint = 0.039 |
8378 independent reflections | |
Refinement top
R[F2 > 2σ(F2)] = 0.054 | 0 restraints |
wR(F2) = 0.152 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.02 | Δρmax = 0.24 e Å−3 |
8378 reflections | Δρmin = −0.27 e Å−3 |
512 parameters | |
Special details top
Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are
estimated using the full covariance matrix. The cell s.u.'s are taken into
account individually in the estimation of s.u.'s in distances, angles and
torsion angles; correlations between s.u.'s in cell parameters are only used
when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell s.u.'s is used for estimating s.u.'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 >
2σ(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 | x | y | z | Uiso*/Ueq | |
S1A | 0.17904 (5) | 0.79421 (6) | −0.03767 (5) | 0.0646 (2) | |
S1B | 0.36203 (6) | 0.34197 (7) | 0.55077 (5) | 0.0694 (2) | |
O3B | 0.52135 (14) | 0.35404 (17) | 0.02461 (12) | 0.0722 (5) | |
O2B | 0.25459 (15) | 0.40900 (18) | 0.52211 (13) | 0.0816 (6) | |
O1B | 0.41481 (16) | 0.3584 (2) | 0.62501 (13) | 0.0854 (6) | |
N1A | 0.24599 (18) | 0.70776 (19) | 0.05831 (16) | 0.0661 (6) | |
O1A | 0.21279 (16) | 0.73965 (17) | −0.10896 (14) | 0.0795 (5) | |
O2A | 0.05999 (14) | 0.81540 (18) | −0.00745 (14) | 0.0799 (5) | |
O4B | −0.05735 (17) | 0.4984 (2) | −0.28263 (16) | 0.0947 (6) | |
O3A | 0.31611 (18) | 0.7139 (2) | 0.47768 (16) | 0.1072 (8) | |
C7B | 0.4446 (2) | 0.3629 (2) | 0.36402 (17) | 0.0602 (6) | |
C16B | 0.2188 (2) | 0.4344 (2) | −0.11850 (18) | 0.0582 (6) | |
C17B | 0.2373 (2) | 0.4527 (2) | −0.21827 (18) | 0.0635 (6) | |
H17B | 0.3123 | 0.4498 | −0.2471 | 0.076* | |
N1B | 0.45667 (19) | 0.3690 (2) | 0.45617 (16) | 0.0751 (7) | |
C11B | 0.3353 (2) | 0.3661 (3) | 0.23888 (19) | 0.0766 (8) | |
H11B | 0.2642 | 0.3687 | 0.218 | 0.092* | |
C7A | 0.2392 (2) | 0.7274 (2) | 0.14772 (18) | 0.0602 (6) | |
C21B | 0.1051 (2) | 0.4378 (2) | −0.0777 (2) | 0.0706 (7) | |
H21B | 0.0897 | 0.425 | −0.011 | 0.085* | |
C12B | 0.3402 (2) | 0.3639 (3) | 0.3323 (2) | 0.0850 (9) | |
H12B | 0.2734 | 0.3631 | 0.3741 | 0.102* | |
C15B | 0.3171 (2) | 0.4082 (2) | −0.06264 (18) | 0.0601 (6) | |
H15B | 0.3879 | 0.3988 | −0.0971 | 0.072* | |
C18B | 0.1485 (2) | 0.4750 (2) | −0.27569 (19) | 0.0689 (7) | |
H18B | 0.1635 | 0.4873 | −0.3423 | 0.083* | |
C8B | 0.5424 (2) | 0.3574 (2) | 0.30272 (18) | 0.0647 (6) | |
H8B | 0.6135 | 0.3533 | 0.3242 | 0.078* | |
C13B | 0.4309 (2) | 0.3695 (2) | 0.07319 (17) | 0.0565 (6) | |
C9B | 0.5370 (2) | 0.3578 (2) | 0.21029 (18) | 0.0630 (6) | |
H9B | 0.6046 | 0.3535 | 0.1703 | 0.076* | |
C1A | 0.2357 (2) | 0.9295 (2) | −0.07958 (17) | 0.0630 (6) | |
C10B | 0.43259 (19) | 0.3645 (2) | 0.17527 (17) | 0.0546 (5) | |
O4A | −0.2762 (2) | 0.9286 (3) | 0.78912 (19) | 0.1242 (9) | |
C14B | 0.3211 (2) | 0.3955 (2) | 0.03014 (18) | 0.0618 (6) | |
H14B | 0.253 | 0.4032 | 0.0687 | 0.074* | |
C13A | 0.2292 (3) | 0.7493 (3) | 0.4336 (2) | 0.0765 (8) | |
C10A | 0.2314 (2) | 0.7464 (2) | 0.3332 (2) | 0.0689 (7) | |
C16A | 0.0107 (3) | 0.8190 (2) | 0.62976 (19) | 0.0719 (7) | |
C6A | 0.1643 (3) | 1.0319 (3) | −0.0857 (2) | 0.0810 (8) | |
H6A | 0.0865 | 1.0294 | −0.0652 | 0.097* | |
C11A | 0.1398 (2) | 0.7892 (3) | 0.2768 (2) | 0.0840 (9) | |
H11A | 0.0735 | 0.826 | 0.3007 | 0.101* | |
C21A | −0.0923 (3) | 0.8748 (3) | 0.5895 (2) | 0.0926 (9) | |
H21A | −0.0983 | 0.889 | 0.5237 | 0.111* | |
C15A | 0.1104 (3) | 0.7821 (3) | 0.5737 (2) | 0.0760 (8) | |
H15A | 0.1746 | 0.7466 | 0.6083 | 0.091* | |
C1B | 0.3442 (3) | 0.1908 (3) | 0.58692 (18) | 0.0731 (7) | |
C5A | 0.2092 (3) | 1.1388 (3) | −0.1228 (3) | 0.0997 (10) | |
H5A | 0.1613 | 1.2089 | −0.1283 | 0.12* | |
C19B | 0.0369 (2) | 0.4788 (2) | −0.2336 (2) | 0.0690 (7) | |
C12A | 0.1428 (2) | 0.7795 (3) | 0.1863 (2) | 0.0888 (9) | |
H12A | 0.0786 | 0.8086 | 0.1509 | 0.107* | |
C8A | 0.3326 (2) | 0.6855 (3) | 0.2022 (2) | 0.0859 (9) | |
H8A | 0.3995 | 0.6507 | 0.1773 | 0.103* | |
C17A | 0.0138 (3) | 0.8004 (3) | 0.7279 (2) | 0.0867 (9) | |
H17A | 0.0808 | 0.7627 | 0.7575 | 0.104* | |
C18A | −0.0784 (3) | 0.8354 (3) | 0.7838 (2) | 0.0889 (9) | |
H18A | −0.0728 | 0.8222 | 0.8495 | 0.107* | |
C19A | −0.1785 (3) | 0.8901 (3) | 0.7413 (2) | 0.0907 (9) | |
C2A | 0.3500 (3) | 0.9334 (3) | −0.1101 (3) | 0.0908 (9) | |
H2A | 0.398 | 0.864 | −0.1067 | 0.109* | |
C14A | 0.1232 (3) | 0.7920 (3) | 0.4799 (2) | 0.0790 (8) | |
H14A | 0.0615 | 0.8277 | 0.4421 | 0.095* | |
C22B | −0.0381 (3) | 0.5009 (3) | −0.3814 (3) | 0.1051 (11) | |
H22A | −0.1104 | 0.5143 | −0.408 | 0.158* | |
H22B | 0.0024 | 0.4265 | −0.382 | 0.158* | |
H22C | 0.0067 | 0.5638 | −0.4203 | 0.158* | |
C20B | 0.0157 (2) | 0.4595 (3) | −0.1338 (2) | 0.0755 (8) | |
H20B | −0.0594 | 0.4612 | −0.1051 | 0.091* | |
C4A | 0.3235 (4) | 1.1419 (3) | −0.1512 (2) | 0.0980 (10) | |
H4A | 0.3538 | 1.2138 | −0.1744 | 0.118* | |
C4B | 0.3128 (6) | −0.0426 (4) | 0.6518 (3) | 0.1318 (15) | |
H4B | 0.302 | −0.1222 | 0.6734 | 0.158* | |
C3A | 0.3934 (3) | 1.0399 (3) | −0.1455 (3) | 0.1055 (11) | |
H3A | 0.4712 | 1.0425 | −0.1659 | 0.127* | |
C9A | 0.3279 (3) | 0.6945 (3) | 0.2930 (2) | 0.0925 (10) | |
H9A | 0.3919 | 0.6646 | 0.3286 | 0.111* | |
C20A | −0.1851 (3) | 0.9093 (3) | 0.6440 (3) | 0.1008 (10) | |
H20A | −0.2528 | 0.9459 | 0.6151 | 0.121* | |
C6B | 0.2361 (3) | 0.1570 (4) | 0.6157 (2) | 0.0991 (10) | |
H6B | 0.1729 | 0.2142 | 0.6121 | 0.119* | |
C5B | 0.2204 (4) | 0.0392 (5) | 0.6498 (3) | 0.1245 (15) | |
H5B | 0.1474 | 0.0161 | 0.6711 | 0.149* | |
C3B | 0.4211 (5) | −0.0121 (4) | 0.6233 (4) | 0.1494 (19) | |
H3B | 0.4834 | −0.0698 | 0.6251 | 0.179* | |
C2B | 0.4373 (4) | 0.1087 (4) | 0.5910 (3) | 0.1212 (13) | |
H2B | 0.5106 | 0.1316 | 0.5727 | 0.145* | |
C22A | −0.2706 (4) | 0.9231 (4) | 0.8865 (3) | 0.1404 (16) | |
H22D | −0.344 | 0.953 | 0.9108 | 0.211* | |
H22E | −0.2136 | 0.9704 | 0.8865 | 0.211* | |
H22F | −0.2505 | 0.8423 | 0.928 | 0.211* | |
H1B | 0.521 (4) | 0.361 (4) | 0.471 (3) | 0.169* | |
H1A | 0.308 (4) | 0.679 (4) | 0.040 (3) | 0.169* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
S1A | 0.0553 (4) | 0.0775 (4) | 0.0618 (4) | 0.0065 (3) | −0.0138 (3) | −0.0289 (3) |
S1B | 0.0604 (4) | 0.1005 (5) | 0.0534 (4) | −0.0051 (4) | −0.0090 (3) | −0.0352 (4) |
O3B | 0.0583 (10) | 0.0951 (13) | 0.0643 (11) | 0.0153 (9) | −0.0088 (8) | −0.0392 (10) |
O2B | 0.0657 (11) | 0.1114 (15) | 0.0710 (12) | 0.0104 (10) | −0.0165 (9) | −0.0414 (11) |
O1B | 0.0745 (12) | 0.1324 (17) | 0.0662 (11) | −0.0121 (11) | −0.0132 (9) | −0.0524 (12) |
N1A | 0.0606 (13) | 0.0687 (13) | 0.0635 (13) | 0.0062 (11) | −0.0115 (10) | −0.0211 (11) |
O1A | 0.0751 (12) | 0.0964 (14) | 0.0790 (12) | 0.0091 (10) | −0.0203 (10) | −0.0484 (11) |
O2A | 0.0517 (10) | 0.1042 (15) | 0.0810 (12) | 0.0051 (10) | −0.0121 (9) | −0.0340 (11) |
O4B | 0.0730 (13) | 0.1227 (17) | 0.1015 (16) | 0.0099 (12) | −0.0369 (11) | −0.0536 (14) |
O3A | 0.0757 (14) | 0.164 (2) | 0.0926 (15) | 0.0032 (14) | −0.0336 (12) | −0.0555 (15) |
C7B | 0.0583 (14) | 0.0712 (16) | 0.0510 (13) | −0.0083 (12) | −0.0085 (11) | −0.0204 (12) |
C16B | 0.0558 (14) | 0.0639 (15) | 0.0597 (14) | 0.0014 (11) | −0.0119 (11) | −0.0290 (12) |
C17B | 0.0593 (15) | 0.0751 (17) | 0.0599 (15) | −0.0029 (12) | −0.0062 (12) | −0.0305 (13) |
N1B | 0.0599 (13) | 0.1186 (19) | 0.0549 (12) | −0.0170 (13) | −0.0065 (10) | −0.0374 (13) |
C11B | 0.0513 (14) | 0.122 (2) | 0.0639 (16) | −0.0070 (15) | −0.0116 (12) | −0.0412 (16) |
C7A | 0.0553 (14) | 0.0580 (14) | 0.0621 (15) | −0.0011 (11) | −0.0114 (12) | −0.0159 (12) |
C21B | 0.0653 (16) | 0.0911 (19) | 0.0630 (16) | 0.0027 (14) | −0.0069 (13) | −0.0411 (15) |
C12B | 0.0521 (15) | 0.150 (3) | 0.0620 (16) | −0.0130 (16) | −0.0034 (12) | −0.0483 (18) |
C15B | 0.0570 (14) | 0.0673 (15) | 0.0591 (14) | 0.0024 (12) | −0.0082 (11) | −0.0294 (12) |
C18B | 0.0739 (17) | 0.0772 (17) | 0.0601 (15) | −0.0018 (14) | −0.0158 (13) | −0.0292 (13) |
C8B | 0.0514 (14) | 0.0833 (18) | 0.0603 (15) | −0.0081 (12) | −0.0112 (11) | −0.0246 (13) |
C13B | 0.0575 (14) | 0.0554 (13) | 0.0564 (14) | 0.0043 (11) | −0.0095 (11) | −0.0230 (11) |
C9B | 0.0479 (13) | 0.0803 (17) | 0.0600 (15) | −0.0009 (12) | −0.0055 (11) | −0.0268 (13) |
C1A | 0.0626 (15) | 0.0704 (16) | 0.0516 (13) | 0.0099 (13) | −0.0095 (11) | −0.0226 (12) |
C10B | 0.0537 (13) | 0.0562 (13) | 0.0531 (13) | 0.0010 (11) | −0.0097 (10) | −0.0201 (11) |
O4A | 0.126 (2) | 0.159 (2) | 0.1018 (18) | −0.0054 (18) | −0.0049 (16) | −0.0699 (17) |
C14B | 0.0543 (14) | 0.0764 (16) | 0.0590 (15) | 0.0043 (12) | −0.0090 (11) | −0.0327 (13) |
C13A | 0.0696 (18) | 0.089 (2) | 0.0734 (18) | −0.0095 (15) | −0.0217 (15) | −0.0258 (15) |
C10A | 0.0612 (16) | 0.0761 (17) | 0.0700 (17) | −0.0040 (13) | −0.0155 (13) | −0.0251 (14) |
C16A | 0.0840 (19) | 0.0770 (18) | 0.0593 (15) | −0.0168 (15) | −0.0189 (14) | −0.0223 (14) |
C6A | 0.0802 (19) | 0.079 (2) | 0.0747 (19) | 0.0129 (16) | −0.0063 (15) | −0.0275 (16) |
C11A | 0.0661 (17) | 0.114 (2) | 0.0673 (17) | 0.0186 (16) | −0.0137 (14) | −0.0364 (17) |
C21A | 0.100 (2) | 0.120 (3) | 0.0650 (18) | −0.002 (2) | −0.0263 (17) | −0.0391 (18) |
C15A | 0.0801 (19) | 0.0826 (19) | 0.0682 (17) | −0.0127 (15) | −0.0256 (15) | −0.0221 (15) |
C1B | 0.0768 (18) | 0.093 (2) | 0.0503 (14) | −0.0054 (16) | −0.0095 (13) | −0.0269 (14) |
C5A | 0.118 (3) | 0.074 (2) | 0.092 (2) | 0.012 (2) | −0.004 (2) | −0.0243 (18) |
C19B | 0.0652 (16) | 0.0740 (17) | 0.0773 (18) | 0.0078 (13) | −0.0270 (14) | −0.0371 (14) |
C12A | 0.0637 (17) | 0.127 (3) | 0.0692 (18) | 0.0210 (17) | −0.0213 (14) | −0.0364 (18) |
C8A | 0.0595 (16) | 0.114 (2) | 0.092 (2) | 0.0184 (16) | −0.0214 (15) | −0.0536 (19) |
C17A | 0.097 (2) | 0.102 (2) | 0.0659 (18) | −0.0175 (18) | −0.0259 (17) | −0.0260 (17) |
C18A | 0.108 (3) | 0.108 (2) | 0.0611 (17) | −0.028 (2) | −0.0124 (18) | −0.0346 (17) |
C19A | 0.103 (3) | 0.102 (2) | 0.078 (2) | −0.021 (2) | −0.0070 (19) | −0.0424 (19) |
C2A | 0.0691 (19) | 0.074 (2) | 0.116 (3) | 0.0040 (16) | −0.0033 (17) | −0.0263 (18) |
C14A | 0.0752 (19) | 0.098 (2) | 0.0655 (17) | −0.0035 (16) | −0.0215 (14) | −0.0293 (16) |
C22B | 0.099 (2) | 0.136 (3) | 0.099 (2) | 0.002 (2) | −0.050 (2) | −0.055 (2) |
C20B | 0.0546 (15) | 0.101 (2) | 0.0814 (19) | 0.0029 (14) | −0.0103 (13) | −0.0483 (17) |
C4A | 0.121 (3) | 0.078 (2) | 0.085 (2) | −0.014 (2) | −0.002 (2) | −0.0197 (17) |
C4B | 0.179 (5) | 0.113 (3) | 0.105 (3) | −0.033 (4) | −0.019 (3) | −0.032 (3) |
C3A | 0.084 (2) | 0.092 (2) | 0.124 (3) | −0.010 (2) | 0.003 (2) | −0.025 (2) |
C9A | 0.0646 (18) | 0.129 (3) | 0.094 (2) | 0.0162 (18) | −0.0349 (16) | −0.053 (2) |
C20A | 0.089 (2) | 0.133 (3) | 0.087 (2) | 0.006 (2) | −0.0235 (18) | −0.050 (2) |
C6B | 0.089 (2) | 0.116 (3) | 0.090 (2) | −0.019 (2) | −0.0312 (18) | −0.024 (2) |
C5B | 0.132 (4) | 0.127 (4) | 0.109 (3) | −0.046 (3) | −0.045 (3) | −0.011 (3) |
C3B | 0.167 (5) | 0.107 (4) | 0.137 (4) | 0.012 (3) | 0.030 (3) | −0.029 (3) |
C2B | 0.111 (3) | 0.110 (3) | 0.117 (3) | 0.000 (2) | 0.026 (2) | −0.030 (2) |
C22A | 0.186 (5) | 0.159 (4) | 0.090 (3) | −0.029 (3) | 0.015 (3) | −0.067 (3) |
Geometric parameters (Å, º) top
S1A—O1A | 1.4220 (18) | C10A—C9A | 1.381 (4) |
S1A—O2A | 1.4293 (17) | C16A—C17A | 1.381 (4) |
S1A—N1A | 1.637 (2) | C16A—C21A | 1.393 (4) |
S1A—C1A | 1.749 (3) | C16A—C15A | 1.451 (4) |
S1B—O2B | 1.4235 (19) | C6A—C5A | 1.382 (4) |
S1B—O1B | 1.4258 (18) | C6A—H6A | 0.93 |
S1B—N1B | 1.624 (2) | C11A—C12A | 1.377 (4) |
S1B—C1B | 1.764 (3) | C11A—H11A | 0.93 |
O3B—C13B | 1.229 (3) | C21A—C20A | 1.371 (4) |
N1A—C7A | 1.414 (3) | C21A—H21A | 0.93 |
N1A—H1A | 0.82 (4) | C15A—C14A | 1.330 (4) |
O4B—C19B | 1.359 (3) | C15A—H15A | 0.93 |
O4B—C22B | 1.428 (4) | C1B—C2B | 1.356 (4) |
O3A—C13A | 1.228 (3) | C1B—C6B | 1.373 (4) |
C7B—C8B | 1.372 (3) | C5A—C4A | 1.362 (5) |
C7B—C12B | 1.382 (3) | C5A—H5A | 0.93 |
C7B—N1B | 1.416 (3) | C19B—C20B | 1.389 (4) |
C16B—C17B | 1.391 (3) | C12A—H12A | 0.93 |
C16B—C21B | 1.396 (3) | C8A—C9A | 1.375 (4) |
C16B—C15B | 1.447 (3) | C8A—H8A | 0.93 |
C17B—C18B | 1.375 (3) | C17A—C18A | 1.381 (4) |
C17B—H17B | 0.93 | C17A—H17A | 0.93 |
N1B—H1B | 0.80 (4) | C18A—C19A | 1.374 (4) |
C11B—C12B | 1.376 (4) | C18A—H18A | 0.93 |
C11B—C10B | 1.380 (3) | C19A—C20A | 1.374 (4) |
C11B—H11B | 0.93 | C2A—C3A | 1.369 (4) |
C7A—C12A | 1.371 (4) | C2A—H2A | 0.93 |
C7A—C8A | 1.377 (3) | C14A—H14A | 0.93 |
C21B—C20B | 1.370 (4) | C22B—H22A | 0.96 |
C21B—H21B | 0.93 | C22B—H22B | 0.96 |
C12B—H12B | 0.93 | C22B—H22C | 0.96 |
C15B—C14B | 1.323 (3) | C20B—H20B | 0.93 |
C15B—H15B | 0.93 | C4A—C3A | 1.361 (5) |
C18B—C19B | 1.379 (4) | C4A—H4A | 0.93 |
C18B—H18B | 0.93 | C4B—C5B | 1.351 (6) |
C8B—C9B | 1.370 (3) | C4B—C3B | 1.362 (6) |
C8B—H8B | 0.93 | C4B—H4B | 0.93 |
C13B—C14B | 1.467 (3) | C3A—H3A | 0.93 |
C13B—C10B | 1.485 (3) | C9A—H9A | 0.93 |
C9B—C10B | 1.389 (3) | C20A—H20A | 0.93 |
C9B—H9B | 0.93 | C6B—C5B | 1.374 (5) |
C1A—C2A | 1.368 (4) | C6B—H6B | 0.93 |
C1A—C6A | 1.372 (4) | C5B—H5B | 0.93 |
O4A—C19A | 1.375 (4) | C3B—C2B | 1.411 (6) |
O4A—C22A | 1.421 (4) | C3B—H3B | 0.93 |
C14B—H14B | 0.93 | C2B—H2B | 0.93 |
C13A—C14A | 1.456 (4) | C22A—H22D | 0.96 |
C13A—C10A | 1.489 (4) | C22A—H22E | 0.96 |
C10A—C11A | 1.376 (4) | C22A—H22F | 0.96 |
| | | |
O1A—S1A—O2A | 119.61 (12) | C12A—C11A—H11A | 118.8 |
O1A—S1A—N1A | 104.80 (11) | C20A—C21A—C16A | 121.9 (3) |
O2A—S1A—N1A | 109.01 (11) | C20A—C21A—H21A | 119 |
O1A—S1A—C1A | 108.43 (12) | C16A—C21A—H21A | 119 |
O2A—S1A—C1A | 107.90 (12) | C14A—C15A—C16A | 129.1 (3) |
N1A—S1A—C1A | 106.36 (12) | C14A—C15A—H15A | 115.4 |
O2B—S1B—O1B | 119.17 (12) | C16A—C15A—H15A | 115.4 |
O2B—S1B—N1B | 109.69 (12) | C2B—C1B—C6B | 120.6 (3) |
O1B—S1B—N1B | 105.01 (12) | C2B—C1B—S1B | 120.0 (3) |
O2B—S1B—C1B | 107.17 (13) | C6B—C1B—S1B | 119.3 (3) |
O1B—S1B—C1B | 109.08 (13) | C4A—C5A—C6A | 120.2 (3) |
N1B—S1B—C1B | 106.03 (13) | C4A—C5A—H5A | 119.9 |
C7A—N1A—S1A | 125.13 (17) | C6A—C5A—H5A | 119.9 |
C7A—N1A—H1A | 116 (3) | O4B—C19B—C18B | 124.5 (3) |
S1A—N1A—H1A | 110 (3) | O4B—C19B—C20B | 115.7 (3) |
C19B—O4B—C22B | 116.9 (2) | C18B—C19B—C20B | 119.7 (2) |
C8B—C7B—C12B | 118.7 (2) | C7A—C12A—C11A | 120.8 (3) |
C8B—C7B—N1B | 117.6 (2) | C7A—C12A—H12A | 119.6 |
C12B—C7B—N1B | 123.7 (2) | C11A—C12A—H12A | 119.6 |
C17B—C16B—C21B | 117.1 (2) | C9A—C8A—C7A | 120.6 (3) |
C17B—C16B—C15B | 118.8 (2) | C9A—C8A—H8A | 119.7 |
C21B—C16B—C15B | 124.0 (2) | C7A—C8A—H8A | 119.7 |
C18B—C17B—C16B | 122.3 (2) | C18A—C17A—C16A | 122.8 (3) |
C18B—C17B—H17B | 118.9 | C18A—C17A—H17A | 118.6 |
C16B—C17B—H17B | 118.9 | C16A—C17A—H17A | 118.6 |
C7B—N1B—S1B | 126.34 (18) | C19A—C18A—C17A | 119.2 (3) |
C7B—N1B—H1B | 117 (3) | C19A—C18A—H18A | 120.4 |
S1B—N1B—H1B | 112 (3) | C17A—C18A—H18A | 120.4 |
C12B—C11B—C10B | 121.9 (2) | C20A—C19A—C18A | 119.6 (3) |
C12B—C11B—H11B | 119 | C20A—C19A—O4A | 115.6 (3) |
C10B—C11B—H11B | 119 | C18A—C19A—O4A | 124.8 (3) |
C12A—C7A—C8A | 117.9 (3) | C1A—C2A—C3A | 119.7 (3) |
C12A—C7A—N1A | 123.8 (2) | C1A—C2A—H2A | 120.1 |
C8A—C7A—N1A | 118.1 (2) | C3A—C2A—H2A | 120.1 |
C20B—C21B—C16B | 121.3 (2) | C15A—C14A—C13A | 122.9 (3) |
C20B—C21B—H21B | 119.3 | C15A—C14A—H14A | 118.5 |
C16B—C21B—H21B | 119.3 | C13A—C14A—H14A | 118.5 |
C11B—C12B—C7B | 120.0 (2) | O4B—C22B—H22A | 109.5 |
C11B—C12B—H12B | 120 | O4B—C22B—H22B | 109.5 |
C7B—C12B—H12B | 120 | H22A—C22B—H22B | 109.5 |
C14B—C15B—C16B | 129.6 (2) | O4B—C22B—H22C | 109.5 |
C14B—C15B—H15B | 115.2 | H22A—C22B—H22C | 109.5 |
C16B—C15B—H15B | 115.2 | H22B—C22B—H22C | 109.5 |
C17B—C18B—C19B | 119.4 (2) | C21B—C20B—C19B | 120.2 (2) |
C17B—C18B—H18B | 120.3 | C21B—C20B—H20B | 119.9 |
C19B—C18B—H18B | 120.3 | C19B—C20B—H20B | 119.9 |
C9B—C8B—C7B | 121.0 (2) | C3A—C4A—C5A | 120.1 (3) |
C9B—C8B—H8B | 119.5 | C3A—C4A—H4A | 120 |
C7B—C8B—H8B | 119.5 | C5A—C4A—H4A | 120 |
O3B—C13B—C14B | 120.4 (2) | C5B—C4B—C3B | 122.0 (5) |
O3B—C13B—C10B | 120.0 (2) | C5B—C4B—H4B | 119 |
C14B—C13B—C10B | 119.7 (2) | C3B—C4B—H4B | 119 |
C8B—C9B—C10B | 121.2 (2) | C4A—C3A—C2A | 120.4 (3) |
C8B—C9B—H9B | 119.4 | C4A—C3A—H3A | 119.8 |
C10B—C9B—H9B | 119.4 | C2A—C3A—H3A | 119.8 |
C2A—C1A—C6A | 120.3 (3) | C8A—C9A—C10A | 122.3 (3) |
C2A—C1A—S1A | 119.9 (2) | C8A—C9A—H9A | 118.9 |
C6A—C1A—S1A | 119.8 (2) | C10A—C9A—H9A | 118.9 |
C11B—C10B—C9B | 117.1 (2) | C21A—C20A—C19A | 120.3 (3) |
C11B—C10B—C13B | 123.7 (2) | C21A—C20A—H20A | 119.9 |
C9B—C10B—C13B | 119.2 (2) | C19A—C20A—H20A | 119.9 |
C19A—O4A—C22A | 118.1 (3) | C1B—C6B—C5B | 120.5 (4) |
C15B—C14B—C13B | 121.2 (2) | C1B—C6B—H6B | 119.7 |
C15B—C14B—H14B | 119.4 | C5B—C6B—H6B | 119.7 |
C13B—C14B—H14B | 119.4 | C4B—C5B—C6B | 119.0 (4) |
O3A—C13A—C14A | 120.3 (3) | C4B—C5B—H5B | 120.5 |
O3A—C13A—C10A | 119.9 (3) | C6B—C5B—H5B | 120.5 |
C14A—C13A—C10A | 119.7 (2) | C4B—C3B—C2B | 118.9 (4) |
C11A—C10A—C9A | 116.1 (3) | C4B—C3B—H3B | 120.6 |
C11A—C10A—C13A | 123.9 (3) | C2B—C3B—H3B | 120.6 |
C9A—C10A—C13A | 120.0 (3) | C1B—C2B—C3B | 119.0 (4) |
C17A—C16A—C21A | 116.1 (3) | C1B—C2B—H2B | 120.5 |
C17A—C16A—C15A | 120.7 (3) | C3B—C2B—H2B | 120.5 |
C21A—C16A—C15A | 123.2 (3) | O4A—C22A—H22D | 109.5 |
C1A—C6A—C5A | 119.2 (3) | O4A—C22A—H22E | 109.5 |
C1A—C6A—H6A | 120.4 | H22D—C22A—H22E | 109.5 |
C5A—C6A—H6A | 120.4 | O4A—C22A—H22F | 109.5 |
C10A—C11A—C12A | 122.3 (3) | H22D—C22A—H22F | 109.5 |
C10A—C11A—H11A | 118.8 | H22E—C22A—H22F | 109.5 |
| | | |
O1A—S1A—N1A—C7A | 179.4 (2) | C17A—C16A—C15A—C14A | 179.6 (3) |
O2A—S1A—N1A—C7A | −51.5 (2) | C21A—C16A—C15A—C14A | −0.7 (5) |
C1A—S1A—N1A—C7A | 64.6 (2) | O2B—S1B—C1B—C2B | 161.1 (3) |
C21B—C16B—C17B—C18B | 0.9 (4) | O1B—S1B—C1B—C2B | −68.6 (3) |
C15B—C16B—C17B—C18B | 178.3 (2) | N1B—S1B—C1B—C2B | 44.0 (3) |
C8B—C7B—N1B—S1B | −162.9 (2) | O2B—S1B—C1B—C6B | −22.3 (3) |
C12B—C7B—N1B—S1B | 18.1 (4) | O1B—S1B—C1B—C6B | 108.0 (2) |
O2B—S1B—N1B—C7B | −51.6 (3) | N1B—S1B—C1B—C6B | −139.4 (2) |
O1B—S1B—N1B—C7B | 179.2 (2) | C1A—C6A—C5A—C4A | −1.1 (5) |
C1B—S1B—N1B—C7B | 63.8 (3) | C22B—O4B—C19B—C18B | 7.7 (4) |
S1A—N1A—C7A—C12A | 33.5 (4) | C22B—O4B—C19B—C20B | −170.9 (3) |
S1A—N1A—C7A—C8A | −150.6 (2) | C17B—C18B—C19B—O4B | −179.0 (3) |
C17B—C16B—C21B—C20B | −0.7 (4) | C17B—C18B—C19B—C20B | −0.4 (4) |
C15B—C16B—C21B—C20B | −177.9 (3) | C8A—C7A—C12A—C11A | −0.1 (5) |
C10B—C11B—C12B—C7B | 1.5 (5) | N1A—C7A—C12A—C11A | 175.9 (3) |
C8B—C7B—C12B—C11B | −3.6 (5) | C10A—C11A—C12A—C7A | −0.9 (5) |
N1B—C7B—C12B—C11B | 175.4 (3) | C12A—C7A—C8A—C9A | 0.8 (5) |
C17B—C16B—C15B—C14B | 175.0 (3) | N1A—C7A—C8A—C9A | −175.3 (3) |
C21B—C16B—C15B—C14B | −7.9 (4) | C21A—C16A—C17A—C18A | −0.7 (5) |
C16B—C17B—C18B—C19B | −0.4 (4) | C15A—C16A—C17A—C18A | 179.1 (3) |
C12B—C7B—C8B—C9B | 2.7 (4) | C16A—C17A—C18A—C19A | 0.7 (5) |
N1B—C7B—C8B—C9B | −176.4 (2) | C17A—C18A—C19A—C20A | −0.2 (5) |
C7B—C8B—C9B—C10B | 0.4 (4) | C17A—C18A—C19A—O4A | 179.7 (3) |
O1A—S1A—C1A—C2A | −51.2 (3) | C22A—O4A—C19A—C20A | −173.2 (3) |
O2A—S1A—C1A—C2A | 177.8 (2) | C22A—O4A—C19A—C18A | 6.9 (5) |
N1A—S1A—C1A—C2A | 61.0 (3) | C6A—C1A—C2A—C3A | 0.9 (5) |
O1A—S1A—C1A—C6A | 125.9 (2) | S1A—C1A—C2A—C3A | 178.1 (3) |
O2A—S1A—C1A—C6A | −5.0 (2) | C16A—C15A—C14A—C13A | −179.4 (3) |
N1A—S1A—C1A—C6A | −121.8 (2) | O3A—C13A—C14A—C15A | −8.1 (5) |
C12B—C11B—C10B—C9B | 1.5 (4) | C10A—C13A—C14A—C15A | 170.6 (3) |
C12B—C11B—C10B—C13B | −178.6 (3) | C16B—C21B—C20B—C19B | −0.1 (4) |
C8B—C9B—C10B—C11B | −2.5 (4) | O4B—C19B—C20B—C21B | 179.4 (3) |
C8B—C9B—C10B—C13B | 177.6 (2) | C18B—C19B—C20B—C21B | 0.7 (4) |
O3B—C13B—C10B—C11B | −171.6 (2) | C6A—C5A—C4A—C3A | 1.7 (5) |
C14B—C13B—C10B—C11B | 9.8 (4) | C5A—C4A—C3A—C2A | −0.9 (6) |
O3B—C13B—C10B—C9B | 8.3 (3) | C1A—C2A—C3A—C4A | −0.4 (6) |
C14B—C13B—C10B—C9B | −170.3 (2) | C7A—C8A—C9A—C10A | −0.7 (5) |
C16B—C15B—C14B—C13B | −179.5 (2) | C11A—C10A—C9A—C8A | −0.2 (5) |
O3B—C13B—C14B—C15B | −3.1 (4) | C13A—C10A—C9A—C8A | 177.4 (3) |
C10B—C13B—C14B—C15B | 175.5 (2) | C16A—C21A—C20A—C19A | 0.4 (6) |
O3A—C13A—C10A—C11A | −177.0 (3) | C18A—C19A—C20A—C21A | −0.3 (5) |
C14A—C13A—C10A—C11A | 4.3 (4) | O4A—C19A—C20A—C21A | 179.7 (3) |
O3A—C13A—C10A—C9A | 5.6 (5) | C2B—C1B—C6B—C5B | 0.5 (5) |
C14A—C13A—C10A—C9A | −173.1 (3) | S1B—C1B—C6B—C5B | −176.1 (3) |
C2A—C1A—C6A—C5A | −0.2 (4) | C3B—C4B—C5B—C6B | 1.6 (7) |
S1A—C1A—C6A—C5A | −177.4 (2) | C1B—C6B—C5B—C4B | −1.9 (6) |
C9A—C10A—C11A—C12A | 1.0 (5) | C5B—C4B—C3B—C2B | 0.2 (8) |
C13A—C10A—C11A—C12A | −176.5 (3) | C6B—C1B—C2B—C3B | 1.3 (6) |
C17A—C16A—C21A—C20A | 0.1 (5) | S1B—C1B—C2B—C3B | 177.9 (3) |
C15A—C16A—C21A—C20A | −179.6 (3) | C4B—C3B—C2B—C1B | −1.6 (7) |
Hydrogen-bond geometry (Å, º) topCgA is the centroid calculated through the ring A C atoms of molecule A. |
D—H···A | D—H | H···A | D···A | D—H···A |
N1A—H1A···O3Bi | 0.81 (5) | 2.16 (5) | 2.950 (3) | 166 (5) |
N1B—H1B···O3Aii | 0.81 (5) | 2.11 (5) | 2.892 (3) | 163 (5) |
C9A—H9A···O1Bii | 0.93 | 2.43 | 3.320 (4) | 160 |
C9B—H9B···O1Ai | 0.93 | 2.49 | 3.366 (3) | 157 |
C22B—H22A···O2Biii | 0.96 | 2.40 | 3.317 (4) | 160 |
C22A—H22D···CgAiv | 0.96 | 3.28 | 3.580 (4) | 101 |
C22A—H22E···CgAiv | 0.96 | 3.33 | 3.580 (4) | 97 |
Symmetry codes: (i) −x+1, −y+1, −z; (ii) −x+1, −y+1, −z+1; (iii) −x, −y+1, −z; (iv) −x, −y+2, −z+1. |
(II)
N-{4-[(
E)-3-(4-Ethoxyphenyl)prop-2-enoyl]phenyl}benzenesulfonamide
top
Crystal data top
C23H21NO4S | F(000) = 856 |
Mr = 407.47 | Dx = 1.279 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P2ybc | Cell parameters from 4266 reflections |
a = 8.4506 (2) Å | θ = 2.9–26.4° |
b = 20.1587 (6) Å | µ = 0.18 mm−1 |
c = 14.2120 (3) Å | T = 298 K |
β = 119.098 (2)° | Prism, yellow |
V = 2115.49 (9) Å3 | 0.25 × 0.20 × 0.15 mm |
Z = 4 | |
Data collection top
Nonius KappaCCD area-detector diffractometer | 3072 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.036 |
Detector resolution: 9 pixels mm-1 | θmax = 26.4°, θmin = 3.2° |
CCD scans | h = −10→10 |
7397 measured reflections | k = −23→25 |
4185 independent reflections | l = −17→17 |
Refinement top
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)] = 0.049 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.143 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.05 | w = 1/[σ2(Fo2) + (0.0875P)2 + 0.0704P] where P = (Fo2 + 2Fc2)/3 |
4185 reflections | (Δ/σ)max < 0.001 |
265 parameters | Δρmax = 0.17 e Å−3 |
0 restraints | Δρmin = −0.27 e Å−3 |
Crystal data top
C23H21NO4S | V = 2115.49 (9) Å3 |
Mr = 407.47 | Z = 4 |
Monoclinic, P21/c | Mo Kα radiation |
a = 8.4506 (2) Å | µ = 0.18 mm−1 |
b = 20.1587 (6) Å | T = 298 K |
c = 14.2120 (3) Å | 0.25 × 0.20 × 0.15 mm |
β = 119.098 (2)° | |
Data collection top
Nonius KappaCCD area-detector diffractometer | 3072 reflections with I > 2σ(I) |
7397 measured reflections | Rint = 0.036 |
4185 independent reflections | |
Refinement top
R[F2 > 2σ(F2)] = 0.049 | 0 restraints |
wR(F2) = 0.143 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.05 | Δρmax = 0.17 e Å−3 |
4185 reflections | Δρmin = −0.27 e Å−3 |
265 parameters | |
Special details top
Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are
estimated using the full covariance matrix. The cell s.u.'s are taken into
account individually in the estimation of s.u.'s in distances, angles and
torsion angles; correlations between s.u.'s in cell parameters are only used
when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell s.u.'s is used for estimating s.u.'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 >
2σ(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 | x | y | z | Uiso*/Ueq | |
S1 | 0.65679 (6) | 0.11848 (2) | 0.42888 (3) | 0.05750 (19) | |
N1 | 0.76455 (19) | 0.16732 (8) | 0.53375 (12) | 0.0606 (4) | |
O1 | 0.69037 (17) | 0.14641 (6) | 0.34799 (10) | 0.0709 (4) | |
O2 | 0.70805 (17) | 0.05154 (6) | 0.46160 (10) | 0.0678 (3) | |
O4 | 0.74263 (19) | −0.16891 (7) | 1.27909 (10) | 0.0753 (4) | |
C1 | 0.4242 (2) | 0.12732 (8) | 0.38628 (13) | 0.0546 (4) | |
C7 | 0.7578 (2) | 0.15805 (8) | 0.63097 (14) | 0.0565 (4) | |
C6 | 0.3341 (2) | 0.07890 (9) | 0.41042 (16) | 0.0677 (5) | |
H6 | 0.395 | 0.0414 | 0.4491 | 0.081* | |
C13 | 0.7446 (3) | 0.13877 (10) | 0.92840 (15) | 0.0660 (5) | |
C21 | 0.7434 (3) | −0.05952 (10) | 1.07881 (15) | 0.0723 (5) | |
H21 | 0.7525 | −0.0638 | 1.0165 | 0.087* | |
C10 | 0.7513 (2) | 0.14366 (9) | 0.82493 (14) | 0.0601 (4) | |
C19 | 0.7346 (2) | −0.11021 (9) | 1.22857 (14) | 0.0640 (5) | |
O3 | 0.7338 (2) | 0.18963 (7) | 0.97259 (11) | 0.0833 (4) | |
C22 | 0.7544 (3) | −0.16605 (10) | 1.38310 (15) | 0.0747 (5) | |
H22A | 0.6452 | −0.1466 | 1.3774 | 0.09* | |
H22B | 0.8569 | −0.139 | 1.4315 | 0.09* | |
C15 | 0.7296 (3) | 0.06480 (10) | 1.06029 (15) | 0.0700 (5) | |
H15 | 0.7149 | 0.1035 | 1.0908 | 0.084* | |
C9 | 0.7312 (3) | 0.20515 (9) | 0.77736 (16) | 0.0722 (5) | |
H9 | 0.7166 | 0.2424 | 0.8109 | 0.087* | |
C18 | 0.7174 (3) | −0.04923 (9) | 1.26476 (15) | 0.0693 (5) | |
H18 | 0.7081 | −0.0455 | 1.3271 | 0.083* | |
C17 | 0.7140 (3) | 0.00713 (10) | 1.20731 (15) | 0.0716 (5) | |
H17 | 0.7017 | 0.0484 | 1.2322 | 0.086* | |
C8 | 0.7323 (3) | 0.21237 (9) | 0.68120 (15) | 0.0684 (5) | |
H8 | 0.7157 | 0.2541 | 0.65 | 0.082* | |
C20 | 0.7449 (3) | −0.11520 (10) | 1.13412 (15) | 0.0722 (5) | |
H20 | 0.753 | −0.1568 | 1.1084 | 0.087* | |
C16 | 0.7284 (2) | 0.00392 (9) | 1.11405 (14) | 0.0652 (5) | |
C2 | 0.3369 (3) | 0.18415 (9) | 0.33206 (16) | 0.0700 (5) | |
H2 | 0.4002 | 0.2173 | 0.3189 | 0.084* | |
C12 | 0.7835 (3) | 0.09649 (10) | 0.67957 (16) | 0.0743 (5) | |
H12 | 0.8052 | 0.0596 | 0.6482 | 0.089* | |
C5 | 0.1508 (3) | 0.08715 (10) | 0.37601 (17) | 0.0754 (5) | |
H5 | 0.0882 | 0.055 | 0.3918 | 0.09* | |
C14 | 0.7485 (3) | 0.07314 (10) | 0.97391 (16) | 0.0720 (5) | |
H14 | 0.7649 | 0.036 | 0.9408 | 0.086* | |
C4 | 0.0624 (3) | 0.14239 (10) | 0.31898 (16) | 0.0741 (5) | |
H4 | −0.061 | 0.1471 | 0.2944 | 0.089* | |
C11 | 0.7769 (3) | 0.08960 (10) | 0.77449 (15) | 0.0728 (5) | |
H11 | 0.7901 | 0.0477 | 0.8048 | 0.087* | |
C3 | 0.1549 (3) | 0.19133 (10) | 0.29755 (17) | 0.0783 (5) | |
H3 | 0.0941 | 0.2291 | 0.2598 | 0.094* | |
C23 | 0.7774 (4) | −0.23565 (12) | 1.42532 (19) | 0.0988 (7) | |
H23A | 0.7856 | −0.2351 | 1.4951 | 0.148* | |
H23B | 0.8861 | −0.2544 | 1.4309 | 0.148* | |
H23C | 0.6752 | −0.2619 | 1.377 | 0.148* | |
H1 | 0.763 (3) | 0.2108 (14) | 0.516 (2) | 0.119* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
S1 | 0.0687 (3) | 0.0501 (3) | 0.0675 (3) | −0.00035 (18) | 0.0439 (2) | −0.00150 (18) |
N1 | 0.0657 (8) | 0.0533 (8) | 0.0708 (9) | −0.0046 (6) | 0.0394 (7) | −0.0013 (7) |
O1 | 0.0923 (9) | 0.0643 (8) | 0.0829 (8) | −0.0019 (6) | 0.0637 (8) | 0.0005 (6) |
O2 | 0.0830 (8) | 0.0490 (7) | 0.0819 (8) | 0.0063 (5) | 0.0485 (7) | −0.0001 (6) |
O4 | 0.1070 (10) | 0.0633 (8) | 0.0669 (7) | −0.0010 (7) | 0.0510 (7) | −0.0033 (6) |
C1 | 0.0645 (9) | 0.0506 (9) | 0.0551 (9) | −0.0017 (7) | 0.0340 (8) | 0.0008 (7) |
C7 | 0.0548 (8) | 0.0524 (10) | 0.0644 (10) | −0.0059 (7) | 0.0306 (8) | −0.0057 (8) |
C6 | 0.0702 (11) | 0.0548 (10) | 0.0800 (12) | −0.0034 (8) | 0.0382 (9) | 0.0082 (9) |
C13 | 0.0730 (11) | 0.0624 (11) | 0.0661 (10) | −0.0069 (8) | 0.0367 (9) | −0.0077 (9) |
C21 | 0.0931 (13) | 0.0719 (13) | 0.0617 (10) | −0.0031 (10) | 0.0453 (10) | −0.0083 (9) |
C10 | 0.0624 (9) | 0.0547 (10) | 0.0650 (10) | −0.0055 (8) | 0.0324 (8) | −0.0062 (8) |
C19 | 0.0735 (11) | 0.0605 (11) | 0.0616 (10) | −0.0038 (8) | 0.0356 (9) | −0.0066 (8) |
O3 | 0.1218 (12) | 0.0609 (8) | 0.0834 (9) | −0.0081 (7) | 0.0624 (9) | −0.0125 (7) |
C22 | 0.0906 (13) | 0.0795 (13) | 0.0630 (11) | −0.0084 (10) | 0.0443 (10) | −0.0071 (10) |
C15 | 0.0829 (12) | 0.0629 (11) | 0.0660 (11) | −0.0072 (9) | 0.0378 (10) | −0.0082 (9) |
C9 | 0.0961 (14) | 0.0548 (11) | 0.0798 (12) | −0.0048 (9) | 0.0539 (11) | −0.0092 (9) |
C18 | 0.0853 (12) | 0.0675 (12) | 0.0656 (11) | −0.0111 (9) | 0.0449 (10) | −0.0133 (9) |
C17 | 0.0899 (13) | 0.0631 (12) | 0.0714 (11) | −0.0095 (9) | 0.0466 (10) | −0.0148 (9) |
C8 | 0.0866 (12) | 0.0506 (10) | 0.0780 (12) | −0.0048 (8) | 0.0480 (10) | −0.0030 (9) |
C20 | 0.0974 (14) | 0.0605 (11) | 0.0687 (11) | 0.0015 (9) | 0.0483 (11) | −0.0093 (9) |
C16 | 0.0715 (11) | 0.0628 (11) | 0.0634 (10) | −0.0081 (8) | 0.0345 (9) | −0.0081 (9) |
C2 | 0.0730 (11) | 0.0614 (11) | 0.0834 (12) | 0.0005 (9) | 0.0442 (10) | 0.0143 (9) |
C12 | 0.1028 (14) | 0.0555 (11) | 0.0735 (12) | 0.0111 (10) | 0.0498 (11) | 0.0002 (9) |
C5 | 0.0743 (12) | 0.0674 (13) | 0.0917 (14) | −0.0129 (9) | 0.0462 (11) | 0.0025 (10) |
C14 | 0.0874 (13) | 0.0615 (11) | 0.0742 (12) | −0.0045 (9) | 0.0448 (11) | −0.0070 (9) |
C4 | 0.0628 (10) | 0.0768 (13) | 0.0832 (12) | −0.0003 (9) | 0.0360 (10) | −0.0007 (11) |
C11 | 0.0958 (14) | 0.0563 (11) | 0.0715 (11) | 0.0035 (9) | 0.0447 (11) | 0.0015 (9) |
C3 | 0.0718 (12) | 0.0738 (13) | 0.0887 (13) | 0.0083 (9) | 0.0385 (10) | 0.0169 (11) |
C23 | 0.133 (2) | 0.0928 (17) | 0.0818 (14) | −0.0041 (14) | 0.0610 (15) | 0.0078 (12) |
Geometric parameters (Å, º) top
S1—O2 | 1.4245 (13) | C22—H22B | 0.97 |
S1—O1 | 1.4269 (12) | C15—C14 | 1.324 (3) |
S1—N1 | 1.6432 (15) | C15—C16 | 1.448 (2) |
S1—C1 | 1.7621 (17) | C15—H15 | 0.93 |
N1—C7 | 1.423 (2) | C9—C8 | 1.379 (3) |
N1—H1 | 0.91 (3) | C9—H9 | 0.93 |
O4—C19 | 1.369 (2) | C18—C17 | 1.391 (3) |
O4—C22 | 1.434 (2) | C18—H18 | 0.93 |
C1—C2 | 1.378 (2) | C17—C16 | 1.390 (2) |
C1—C6 | 1.380 (2) | C17—H17 | 0.93 |
C7—C8 | 1.380 (2) | C8—H8 | 0.93 |
C7—C12 | 1.385 (2) | C20—H20 | 0.93 |
C6—C5 | 1.388 (2) | C2—C3 | 1.376 (3) |
C6—H6 | 0.93 | C2—H2 | 0.93 |
C13—O3 | 1.228 (2) | C12—C11 | 1.384 (3) |
C13—C14 | 1.466 (3) | C12—H12 | 0.93 |
C13—C10 | 1.502 (2) | C5—C4 | 1.366 (3) |
C21—C20 | 1.367 (3) | C5—H5 | 0.93 |
C21—C16 | 1.402 (2) | C14—H14 | 0.93 |
C21—H21 | 0.93 | C4—C3 | 1.381 (3) |
C10—C11 | 1.378 (2) | C4—H4 | 0.93 |
C10—C9 | 1.382 (3) | C11—H11 | 0.93 |
C19—C18 | 1.367 (3) | C3—H3 | 0.93 |
C19—C20 | 1.390 (2) | C23—H23A | 0.96 |
C22—C23 | 1.501 (3) | C23—H23B | 0.96 |
C22—H22A | 0.97 | C23—H23C | 0.96 |
| | | |
O2—S1—O1 | 119.26 (7) | C19—C18—C17 | 119.28 (16) |
O2—S1—N1 | 108.97 (8) | C19—C18—H18 | 120.4 |
O1—S1—N1 | 104.76 (8) | C17—C18—H18 | 120.4 |
O2—S1—C1 | 108.62 (7) | C16—C17—C18 | 122.35 (17) |
O1—S1—C1 | 108.00 (8) | C16—C17—H17 | 118.8 |
N1—S1—C1 | 106.53 (7) | C18—C17—H17 | 118.8 |
C7—N1—S1 | 122.41 (11) | C9—C8—C7 | 120.45 (17) |
C7—N1—H1 | 113.0 (16) | C9—C8—H8 | 119.8 |
S1—N1—H1 | 113.6 (17) | C7—C8—H8 | 119.8 |
C19—O4—C22 | 117.85 (14) | C21—C20—C19 | 120.54 (17) |
C2—C1—C6 | 121.14 (16) | C21—C20—H20 | 119.7 |
C2—C1—S1 | 118.74 (12) | C19—C20—H20 | 119.7 |
C6—C1—S1 | 120.09 (13) | C17—C16—C21 | 116.63 (17) |
C8—C7—C12 | 118.61 (16) | C17—C16—C15 | 119.34 (17) |
C8—C7—N1 | 119.22 (15) | C21—C16—C15 | 124.02 (17) |
C12—C7—N1 | 122.11 (15) | C3—C2—C1 | 119.25 (17) |
C1—C6—C5 | 118.90 (17) | C3—C2—H2 | 120.4 |
C1—C6—H6 | 120.5 | C1—C2—H2 | 120.4 |
C5—C6—H6 | 120.5 | C11—C12—C7 | 120.35 (17) |
O3—C13—C14 | 121.27 (17) | C11—C12—H12 | 119.8 |
O3—C13—C10 | 119.55 (17) | C7—C12—H12 | 119.8 |
C14—C13—C10 | 119.18 (16) | C4—C5—C6 | 120.08 (17) |
C20—C21—C16 | 121.40 (17) | C4—C5—H5 | 120 |
C20—C21—H21 | 119.3 | C6—C5—H5 | 120 |
C16—C21—H21 | 119.3 | C15—C14—C13 | 122.46 (18) |
C11—C10—C9 | 117.89 (16) | C15—C14—H14 | 118.8 |
C11—C10—C13 | 123.20 (17) | C13—C14—H14 | 118.8 |
C9—C10—C13 | 118.90 (16) | C5—C4—C3 | 120.54 (18) |
C18—C19—O4 | 124.55 (16) | C5—C4—H4 | 119.7 |
C18—C19—C20 | 119.76 (18) | C3—C4—H4 | 119.7 |
O4—C19—C20 | 115.69 (16) | C10—C11—C12 | 121.23 (18) |
O4—C22—C23 | 107.77 (16) | C10—C11—H11 | 119.4 |
O4—C22—H22A | 110.2 | C12—C11—H11 | 119.4 |
C23—C22—H22A | 110.2 | C2—C3—C4 | 120.03 (18) |
O4—C22—H22B | 110.2 | C2—C3—H3 | 120 |
C23—C22—H22B | 110.2 | C4—C3—H3 | 120 |
H22A—C22—H22B | 108.5 | C22—C23—H23A | 109.5 |
C14—C15—C16 | 129.19 (18) | C22—C23—H23B | 109.5 |
C14—C15—H15 | 115.4 | H23A—C23—H23B | 109.5 |
C16—C15—H15 | 115.4 | C22—C23—H23C | 109.5 |
C8—C9—C10 | 121.40 (17) | H23A—C23—H23C | 109.5 |
C8—C9—H9 | 119.3 | H23B—C23—H23C | 109.5 |
C10—C9—H9 | 119.3 | | |
| | | |
O2—S1—N1—C7 | −54.26 (15) | C12—C7—C8—C9 | −0.5 (3) |
O1—S1—N1—C7 | 177.05 (13) | N1—C7—C8—C9 | −177.83 (16) |
C1—S1—N1—C7 | 62.76 (15) | C16—C21—C20—C19 | −1.1 (3) |
O2—S1—C1—C2 | −167.78 (14) | C18—C19—C20—C21 | 1.9 (3) |
O1—S1—C1—C2 | −37.10 (16) | O4—C19—C20—C21 | −178.15 (18) |
N1—S1—C1—C2 | 74.98 (15) | C18—C17—C16—C21 | 1.1 (3) |
O2—S1—C1—C6 | 14.36 (17) | C18—C17—C16—C15 | −178.05 (18) |
O1—S1—C1—C6 | 145.04 (14) | C20—C21—C16—C17 | −0.4 (3) |
N1—S1—C1—C6 | −102.89 (15) | C20—C21—C16—C15 | 178.72 (19) |
S1—N1—C7—C8 | −135.53 (15) | C14—C15—C16—C17 | 177.28 (19) |
S1—N1—C7—C12 | 47.2 (2) | C14—C15—C16—C21 | −1.8 (3) |
C2—C1—C6—C5 | 2.1 (3) | C6—C1—C2—C3 | −2.7 (3) |
S1—C1—C6—C5 | 179.91 (14) | S1—C1—C2—C3 | 179.41 (15) |
O3—C13—C10—C11 | 175.02 (19) | C8—C7—C12—C11 | 2.3 (3) |
C14—C13—C10—C11 | −5.8 (3) | N1—C7—C12—C11 | 179.61 (17) |
O3—C13—C10—C9 | −4.9 (3) | C1—C6—C5—C4 | 0.2 (3) |
C14—C13—C10—C9 | 174.23 (18) | C16—C15—C14—C13 | 179.29 (18) |
C22—O4—C19—C18 | −7.4 (3) | O3—C13—C14—C15 | 4.3 (3) |
C22—O4—C19—C20 | 172.68 (17) | C10—C13—C14—C15 | −174.90 (17) |
C19—O4—C22—C23 | −175.26 (17) | C6—C5—C4—C3 | −1.8 (3) |
C11—C10—C9—C8 | 1.5 (3) | C9—C10—C11—C12 | 0.4 (3) |
C13—C10—C9—C8 | −178.55 (16) | C13—C10—C11—C12 | −179.56 (17) |
O4—C19—C18—C17 | 178.87 (18) | C7—C12—C11—C10 | −2.3 (3) |
C20—C19—C18—C17 | −1.2 (3) | C1—C2—C3—C4 | 1.1 (3) |
C19—C18—C17—C16 | −0.3 (3) | C5—C4—C3—C2 | 1.2 (3) |
C10—C9—C8—C7 | −1.5 (3) | | |
Hydrogen-bond geometry (Å, º) topCgA is the centroid calculated through the ring A C atoms. |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1···O3i | 0.91 (3) | 2.08 (3) | 2.987 (2) | 175 (3) |
C9—H9···O1ii | 0.93 | 2.34 | 3.228 (2) | 160 |
C23—H23A···CgAiii | 0.96 | 3.04 | 3.816 (3) | 138 |
C2—H2···O4iv | 0.93 | 2.65 | 3.269 (2) | 125 |
C3—H3···O4iv | 0.93 | 2.68 | 3.285 (2) | 124 |
Symmetry codes: (i) x, −y+1/2, z−1/2; (ii) x, −y+1/2, z+1/2; (iii) −x+1, −y, −z+2; (iv) −x+1, y+1/2, −z+3/2. |
Experimental details
| (I) | (II) |
Crystal data |
Chemical formula | C22H19NO4S | C23H21NO4S |
Mr | 393.44 | 407.47 |
Crystal system, space group | Triclinic, P1 | Monoclinic, P21/c |
Temperature (K) | 298 | 298 |
a, b, c (Å) | 11.8650 (3), 12.2420 (3), 14.7287 (3) | 8.4506 (2), 20.1587 (6), 14.2120 (3) |
α, β, γ (°) | 68.075 (1), 81.665 (1), 80.437 (1) | 90, 119.098 (2), 90 |
V (Å3) | 1948.99 (8) | 2115.49 (9) |
Z | 4 | 4 |
Radiation type | Mo Kα | Mo Kα |
µ (mm−1) | 0.19 | 0.18 |
Crystal size (mm) | 0.28 × 0.15 × 0.08 | 0.25 × 0.20 × 0.15 |
|
Data collection |
Diffractometer | Nonius KappaCCD area-detector diffractometer | Nonius KappaCCD area-detector diffractometer |
Absorption correction | – | – |
No. of measured, independent and observed [I > 2σ(I)] reflections | 22723, 8378, 5268 | 7397, 4185, 3072 |
Rint | 0.039 | 0.036 |
(sin θ/λ)max (Å−1) | 0.637 | 0.625 |
|
Refinement |
R[F2 > 2σ(F2)], wR(F2), S | 0.054, 0.152, 1.02 | 0.049, 0.143, 1.05 |
No. of reflections | 8378 | 4185 |
No. of parameters | 512 | 265 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.24, −0.27 | 0.17, −0.27 |
Hydrogen-bond geometry (Å, º) for (I) topCgA is the centroid calculated through the ring A C atoms of molecule A. |
D—H···A | D—H | H···A | D···A | D—H···A |
N1A—H1A···O3Bi | 0.81 (5) | 2.16 (5) | 2.950 (3) | 166 (5) |
N1B—H1B···O3Aii | 0.81 (5) | 2.11 (5) | 2.892 (3) | 163 (5) |
C9A—H9A···O1Bii | 0.93 | 2.43 | 3.320 (4) | 160 |
C9B—H9B···O1Ai | 0.93 | 2.49 | 3.366 (3) | 157 |
C22B—H22A···O2Biii | 0.96 | 2.40 | 3.317 (4) | 160 |
C22A—H22D···CgAiv | 0.96 | 3.28 | 3.580 (4) | 101 |
C22A—H22E···CgAiv | 0.96 | 3.33 | 3.580 (4) | 97 |
Symmetry codes: (i) −x+1, −y+1, −z; (ii) −x+1, −y+1, −z+1; (iii) −x, −y+1, −z; (iv) −x, −y+2, −z+1. |
Hydrogen-bond geometry (Å, º) for (II) topCgA is the centroid calculated through the ring A C atoms. |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1···O3i | 0.91 (3) | 2.08 (3) | 2.987 (2) | 175 (3) |
C9—H9···O1ii | 0.93 | 2.34 | 3.228 (2) | 160 |
C23—H23A···CgAiii | 0.96 | 3.04 | 3.816 (3) | 138 |
C2—H2···O4iv | 0.93 | 2.65 | 3.269 (2) | 125 |
C3—H3···O4iv | 0.93 | 2.68 | 3.285 (2) | 124 |
Symmetry codes: (i) x, −y+1/2, z−1/2; (ii) x, −y+1/2, z+1/2; (iii) −x+1, −y, −z+2; (iv) −x+1, y+1/2, −z+3/2. |
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Compounds containing a sulfonamide group are well known to possess strong antibacterial effects, some of them being widely used against common bacterial diseases mainly due to their low cost, low toxicity and excellent pharmacological profiles (Ozbek et al., 2007). The sulfonamide group is also present in many biologically active compounds, such as antimicrobial, antithyroid, antitumour and antimalarial drugs (Ozdemir et al., 2009; Seo et al., 2010; Domínguez et al., 2005; Connor, 1998; Hanson et al., 1999). In addition, many substituted aromatic and heterocyclic sulfonamides have been synthesized and their activity against glaucoma has been evaluated (Remko et al., 2010). Chalcones containing an arylsulfonamide group are emerging compounds for which antimalarial properties have been already demonstrated (Domínguez et al., 2005).
As part of our ongoing studies of sulfonamides in terms of their structural features (Martins et al., 2009; Fernandes et al., 2011), in this study, the two title arylsulfonamide para-alkoxychalcones, (I) and (II), differing only in one methylene group in the para-alkoxy group on the chalcone skeleton, were synthesized and their crystal structures determined using single-crystal X-ray diffraction. This molecular difference of only one CH2 group is enough to change the crystal assembly and symmetry. Likewise, the absence of methylene in the para-alkoxy group of (I) is also related to the conformational variability observed in this compound.
Because of the slight molecular structure differences between (I) and (II), they crystallize in different crystal systems and space groups. While the crystal structure of (I) was solved in the centrosymmetric triclinic space group P1, with two independent molecules in the asymmetric unit, (II) crystallizes in the monoclinic space group P21/c with only one molecule in the asymmetric unit (Fig. 1).
Compound (I) has two conformers in its crystal structure, labelled A and B. The chalcone molecular backbones of both conformers are almost completely planar (r.m.s. deviations = 0.0537 and 0.0440 Å, respectively, for conformers A and B, with the greatest deviations being -0.2053 Å for atom C18A or 0.2076 Å for atom C8B, where the chalcone plane is defined by atoms C13–C15/O3 and the C atoms of rings B and C in Fig. 1) and therefore similar, even though there are slight rotations about the sulfamyl S1—N1 and sulfonyl S1—C1 bridging bond axes (Fig. 2). More specifically, the chalcone group of conformer A is more planar than that of conformer B. In the latter, there are three slight rotations on the bond axes of: (i) C10B—C13B, which displaces phenyl ring B from the neighbouring carbonyl group [e.g. the C9B—C10B—C13B—O3B torsion angle is 8.3 (4)°, cf. 5.6 (5)° for the corresponding torsion angle in conformer A); (ii) C15B—C16B, twisting the para-alkoxy-substituted phenyl ring C from the C14═C15 group [e.g. the C14B—C15B—C16B—C21B torsion angle is -7.8 (4)°, cf. -0.6 (6)° for the corresponding torsion angle in conformer A]; and (iii) C19B—O4B, setting the methyl group of the methoxy in the para-position out of the phenyl ring C plane [e.g. the C18B—C19B—O4B—C22B torsion angle is 7.8 (4)°, cf. 6.9 (5)° for the corresponding torsion angle in conformer A]. The rotation on this last bond axis is also appreciable in conformer A of (I) and in (II), which also shows a remarkable planarity of its chalcone skeleton (r.m.s. deviation = 0.0371 Å, with the greatest deviation being 0.1563 Å for atom C8), except that the ethyl group is slightly out of the phenyl ring C plane, as mentioned above.
It is interesting to note that in the crystal structure of the only other example of an arylsulfonamide chalcone hybrid found in the Cambridge Structural Database (CSD, Version?; Allen, 2002), namely, 4'-(para-toluenesulfonylamino)-4-hydroxychalcone (TSAHC) (Seo et al., 2010), the chalcone skeleton is strongly twisted, wherein the least-squares planes through the corresponding rings B and C form an angle of 33.9 (8)°. This measurement has values of 10.8 (1), 10.02 (8) and 5.2 (8)° in molecules A and B of (I) and in (II), respectively. In the structure of TSAHC, such a twist may be related to the presence of a further intermolecular classical O—H···O hydrogen bond involving the para-hydroxyl and sulfamyl groups of TSAHC, which does not occur in (I) and (II). However, the N—H···O hydrogen bonding between the amino and carbonyl groups is conserved in the structures of TSAHC, (I) and (II). In all three sulfonamide chalcone derivatives, these N—H···O interactions give rise to infinite one-dimensional ribbons running along the [001] (or [010] in TSAHC) direction (Fig. 3). In the structures of both (I) and (II), each chain has all phenyl rings A always oriented towards the same side of the sulfonamide–chalcone plane (Fig. 3). These ribbons are made up of alternating molecules A and B in (I), while c-glide-related units assemble these supramolecular motifs in (II). The linear ribbons are stacked face-to-face on top of one another, along the b axis in (I) and along the a axis in (II). In contrast, a zigzag chain is formed with 21-screw axis symmetry-related molecules in TSAHC.
In addition to the classical hydrogen bonds, the ribbons in (I) and (II) are supported by C9—H9···O1 hydrogen bonds (Tables 1 and 2). The pairwise interactions co-exist with a degree of coplanarity between sulfonamide–chalcone fragments of the hydrogen-bonded molecules. Between successive molecules along the chain, these fragments, defined as the chalcone plane plus atoms N1 and S1, form dihedral angles of 15.0 and 6.4° in (I) and (II).
Besides the classical hydrogen-bonded assembly of the ribbons of (I) and (II), C9—H9···O1 contacts between the C9—H9 atoms of phenyl ring B as a non-classical hydrogen-bonding donor and a sulfonyl O atom as acceptor also contribute to keeping the molecules of (I) and (II) in contact with the linear N—H···O hydrogen-bonded ribbons. Furthermore, such intermolecular interactions align the sulfonamide–chalcone planes with the ribbons in both structures. However, these planes (the chalcone plane as defined above plus atoms N1 and S1) are aligned with the ribbons in a more planar fashion in (II) than in (I), so that the sulfonamide–chalcone planes of N—H···O hydrogen-bonded molecules form angles of ca 15.0 and 6.4° in (I) and (II), respectively.
The supramolecular assemblies of (I) and (II) are thus similar in the formation of linear ribbons, but the structural similarities between them end there. While the crystal packing of (I) is stabilized by weak C—H···π and π–π interactions, only the former interactions occur in (II). In (I), inversion-related molecules A interact through their CH3 and phenyl A groups in very weak but cooperative C—H···π interactions involving two methyl H atoms [CgA···H22D? = 3.28 Å and CgA···H22E?? = 3.33 Å, where CgA is the centroid calculated through the ring A C atoms of molecule A; symmetry codes: Please provide missing details] (Fig. 4). The phenyl rings of both molecules A and B are further connected by weak π–π interactions in (I), with a CgA···CgA' distance between translation symmetry-related molecules of 3.72 (5) Å (Fig. 4) [Please give details of symmetry code]. However, the CH3 group of the terminal ethoxy group in (II) is involved in C—H···π contacts in this structure and π–π interactions do not occur. The intercalation between the CH3 group of the ethoxy group in (II) leads to the formation of a C23—H23A···CgA interaction [CgA···H23A = 3.04 Å; symmetry code: Please provide missing details], assembling dimers made up of inversion-related molecules (Fig. 5a). In this figure, it is possible to see the occurence of a π–π interaction between the π-electrons of the double bond between the atoms C14 and C15 and the ring B C atoms [CgD···CgBv = 3.56 Å, where CgD is the centroid calculated through atoms C14 and C15, and CgB is the centroid calculated through the ring B C atoms; symmetry code: (v) -x+1, -y, -z+2]. In this structure, the role of the additional methylene group in the crystal packing and symmetry can be also seen in the fact that the alkoxy atom O4 is involved as an acceptor in weak bifurcated non-classical hydrogen bonds, having as donors the neighbouring C2—H2 and C3—H3 groups of phenyl ring A. Both C2—H2···O4 and C3—H3···O4 contacts occur between 21-screw axis symmetry-related molecules assembled into zigzag chains along the [010] direction (Fig. 5b). These contacts and chains are not observed in (I). In the structure of (I), the methoxy group is involved in non-classical C—H···O hydrogen bonding, C22B—H22A···O2B???, as a donor to an O atom of SO2 in an inversion-related molecule B (Fig. 4) [symmetry code: Please provide missing details].
In conclusion, this study presents an interesting example in which a molecular difference of only one CH2 group in the terminal alkoxy group has altered the crystal packing and symmetry in two otherwise identical compounds. While classical hydrogen-bonding patterns are conserved in both structures investigated here, the combination of weak C—H···O, C—H···π and π–π contacts involving the phenyl heads and alkoxy tails differs, and this is responsible for the changes observed in the conformation and intermolecular architecture of these two chalcone–sulfonamide analogues. From a crystallographic point of view, not only are the crystal systems and space groups different for (I) and (II), but the Z' contents also differ. This reveals that their crystal structures must depend on the intermolecular contact patterns involving the methylene group of the alkoxy substituent.