Ethyl 3-[7-eth-oxy-6-(4-meth-oxy-benzene-sulfonamido)-2H-indazol-2-yl]propano-ate.

In the title compound, C(21)H(25)N(3)O(6)S, the dihedral angle between the meth-oxy-benzene and indazole rings is 74.96 (5)°. The crystal packing is stabilized by an N-H⋯O hydrogen bond into a two-dimensional network. In addition, C-H⋯π inter-actions and a π-π contact, with a centroid-centroid distance of 3.5333 (6) Å, are observed. The crystal packing is stabilized by N-H⋯O and C-H⋯O hydrogen bonds.

Related literature

For related structures, see: Abbassi et al. (2011a ▶,b ▶). For the biological activity of sulfonamides, see: Soledade et al. (2006 ▶); Lee & Lee (2002 ▶).

Experimental

Crystal data

C21H25N3O6S

M = 447.50

Triclinic,

a = 9.1163 (4) Å

b = 10.9161 (5) Å

c = 11.2959 (5) Å

α = 77.259 (2)°

β = 77.364 (2)°

γ = 88.562 (2)°

V = 1069.55 (8) Å3

Z = 2

Mo Kα radiation

μ = 0.20 mm−1

T = 296 K

0.32 × 0.31 × 0.19 mm

Data collection

Bruker APEXII CCD detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 2003 ▶) T min = 0.940, T max = 0.964

21582 measured reflections

4187 independent reflections

3834 reflections with I > 2σ(I)

R int = 0.025

Refinement

R[F 2 > 2σ(F 2)] = 0.030

wR(F 2) = 0.084

S = 1.06

4187 reflections

283 parameters

H-atom parameters constrained

Δρmax = 0.30 e Å−3

Δρmin = −0.41 e Å−3

Data collection: APEX2 (Bruker, 2005 ▶); cell refinement: SAINT (Bruker, 2005 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: PLATON (Spek, 2009 ▶); software used to prepare material for publication: publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812007519/fj2520sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812007519/fj2520Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812007519/fj2520Isup3.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C21H25N3O6S	Z = 2
Mr = 447.50	F(000) = 472
Triclinic, P1	Dx = 1.390 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 9.1163 (4) Å	Cell parameters from 256 reflections
b = 10.9161 (5) Å	θ = 1.7–26.3°
c = 11.2959 (5) Å	µ = 0.20 mm−1
α = 77.259 (2)°	T = 296 K
β = 77.364 (2)°	Prism, colourless
γ = 88.562 (2)°	0.32 × 0.31 × 0.19 mm
V = 1069.55 (8) Å3

Bruker APEXII CCD detector diffractometer	4187 independent reflections
Radiation source: fine-focus sealed tube	3834 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.025
ω and φ scans	θmax = 26.0°, θmin = 2.6°
Absorption correction: multi-scan (SADABS; Sheldrick, 2003)	h = −11→10
Tmin = 0.940, Tmax = 0.964	k = −12→13
21582 measured reflections	l = −13→13

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)] = 0.030	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.084	H-atom parameters constrained
S = 1.06	w = 1/[σ2(Fo2) + (0.0428P)2 + 0.3561P] where P = (Fo2 + 2Fc2)/3
4187 reflections	(Δ/σ)max < 0.001
283 parameters	Δρmax = 0.30 e Å−3
0 restraints	Δρmin = −0.41 e Å−3

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	0.34987 (3)	0.85372 (3)	0.15120 (3)	0.02632 (10)
O1	0.72338 (10)	1.00455 (8)	0.23308 (8)	0.0272 (2)
O2	0.35314 (11)	0.92233 (9)	0.02682 (9)	0.0362 (2)
O3	0.20739 (10)	0.82306 (10)	0.23512 (9)	0.0349 (2)
O4	0.67582 (14)	0.38348 (10)	0.15066 (10)	0.0478 (3)
O5	0.90152 (13)	0.62024 (10)	0.77999 (10)	0.0498 (3)
O6	1.08922 (11)	0.60258 (9)	0.62130 (9)	0.0351 (2)
N1	0.44792 (12)	0.94084 (10)	0.20865 (10)	0.0253 (2)
H1N	0.5206	0.9790	0.1474	0.030*
N2	0.79639 (11)	0.92171 (9)	0.48444 (9)	0.0228 (2)
N3	0.76942 (11)	0.87006 (9)	0.60807 (9)	0.0221 (2)
C1	0.79320 (19)	0.36718 (17)	0.04930 (16)	0.0471 (4)
H1A	0.7571	0.3869	−0.0263	0.071*
H1B	0.8247	0.2816	0.0638	0.071*
H1C	0.8768	0.4221	0.0422	0.071*
C2	0.60616 (16)	0.49568 (13)	0.14264 (13)	0.0332 (3)
C3	0.63898 (15)	0.59621 (13)	0.04064 (12)	0.0325 (3)
H3	0.7137	0.5903	−0.0285	0.039*
C4	0.55877 (15)	0.70533 (13)	0.04335 (12)	0.0301 (3)
H4	0.5803	0.7735	−0.0241	0.036*
C5	0.44676 (14)	0.71363 (12)	0.14587 (11)	0.0253 (3)
C6	0.41431 (16)	0.61296 (12)	0.24768 (12)	0.0325 (3)
H6	0.3390	0.6187	0.3164	0.039*
C7	0.49430 (18)	0.50480 (13)	0.24608 (13)	0.0387 (3)
H7	0.4737	0.4374	0.3143	0.046*
C8	0.48957 (13)	0.89671 (11)	0.32512 (11)	0.0220 (2)
C9	0.63068 (13)	0.92982 (10)	0.33424 (11)	0.0214 (2)
C10	0.66831 (13)	0.89481 (10)	0.45259 (11)	0.0206 (2)
C11	0.56294 (13)	0.82540 (10)	0.55620 (11)	0.0213 (2)
C12	0.42007 (13)	0.79075 (11)	0.54333 (11)	0.0241 (2)
H12	0.3517	0.7439	0.6106	0.029*
C13	0.38492 (13)	0.82759 (11)	0.42996 (11)	0.0248 (3)
H13	0.2903	0.8072	0.4207	0.030*
C14	0.86846 (14)	0.95273 (14)	0.19168 (12)	0.0322 (3)
H14A	0.9109	0.9181	0.2633	0.039*
H14B	0.9358	1.0195	0.1380	0.039*
C15	0.85789 (17)	0.85207 (15)	0.12261 (14)	0.0389 (3)
H15A	0.7894	0.7867	0.1747	0.058*
H15B	0.9554	0.8178	0.1001	0.058*
H15C	0.8220	0.8872	0.0488	0.058*
C16	0.63495 (13)	0.81239 (11)	0.65462 (11)	0.0228 (2)
H16	0.5970	0.7715	0.7368	0.027*
C17	0.88488 (14)	0.88388 (12)	0.67592 (12)	0.0262 (3)
H17A	0.8435	0.8573	0.7645	0.031*
H17B	0.9153	0.9717	0.6585	0.031*
C18	1.02110 (14)	0.80682 (12)	0.63999 (12)	0.0283 (3)
H18A	1.0513	0.8232	0.5500	0.034*
H18B	1.1035	0.8337	0.6707	0.034*
C19	0.99400 (14)	0.66782 (12)	0.68980 (12)	0.0283 (3)
C20	1.0816 (2)	0.46675 (14)	0.66528 (16)	0.0480 (4)
H20A	0.9814	0.4346	0.6710	0.058*
H20B	1.1051	0.4436	0.7469	0.058*
C21	1.1945 (2)	0.41394 (17)	0.57294 (18)	0.0606 (5)
H21A	1.1729	0.4411	0.4919	0.091*
H21B	1.1894	0.3239	0.5965	0.091*
H21C	1.2936	0.4431	0.5713	0.091*

	U11	U22	U33	U12	U13	U23
S1	0.02522 (17)	0.02943 (17)	0.02551 (17)	0.00073 (12)	−0.01169 (12)	−0.00246 (12)
O1	0.0282 (5)	0.0253 (4)	0.0243 (4)	−0.0030 (4)	−0.0030 (4)	0.0002 (3)
O2	0.0405 (5)	0.0384 (5)	0.0310 (5)	−0.0014 (4)	−0.0197 (4)	0.0021 (4)
O3	0.0230 (5)	0.0450 (6)	0.0374 (5)	0.0014 (4)	−0.0107 (4)	−0.0064 (4)
O4	0.0668 (8)	0.0344 (6)	0.0392 (6)	0.0135 (5)	−0.0037 (5)	−0.0113 (5)
O5	0.0519 (7)	0.0350 (6)	0.0448 (6)	0.0037 (5)	0.0135 (5)	0.0043 (5)
O6	0.0349 (5)	0.0255 (5)	0.0402 (5)	0.0050 (4)	−0.0016 (4)	−0.0043 (4)
N1	0.0270 (5)	0.0244 (5)	0.0248 (5)	0.0009 (4)	−0.0089 (4)	−0.0030 (4)
N2	0.0229 (5)	0.0218 (5)	0.0236 (5)	0.0011 (4)	−0.0054 (4)	−0.0043 (4)
N3	0.0225 (5)	0.0223 (5)	0.0226 (5)	0.0034 (4)	−0.0066 (4)	−0.0060 (4)
C1	0.0470 (9)	0.0505 (9)	0.0501 (9)	0.0125 (7)	−0.0107 (7)	−0.0253 (8)
C2	0.0419 (8)	0.0284 (7)	0.0318 (7)	0.0012 (6)	−0.0092 (6)	−0.0105 (5)
C3	0.0330 (7)	0.0383 (7)	0.0253 (6)	−0.0042 (6)	−0.0017 (5)	−0.0095 (5)
C4	0.0336 (7)	0.0319 (7)	0.0227 (6)	−0.0049 (5)	−0.0053 (5)	−0.0021 (5)
C5	0.0278 (6)	0.0260 (6)	0.0237 (6)	−0.0035 (5)	−0.0088 (5)	−0.0053 (5)
C6	0.0405 (7)	0.0282 (6)	0.0250 (6)	−0.0040 (5)	0.0005 (5)	−0.0052 (5)
C7	0.0571 (9)	0.0256 (7)	0.0275 (7)	−0.0014 (6)	−0.0006 (6)	−0.0021 (5)
C8	0.0248 (6)	0.0201 (5)	0.0228 (6)	0.0059 (4)	−0.0072 (5)	−0.0066 (4)
C9	0.0237 (6)	0.0172 (5)	0.0225 (6)	0.0022 (4)	−0.0033 (5)	−0.0043 (4)
C10	0.0207 (5)	0.0169 (5)	0.0245 (6)	0.0030 (4)	−0.0045 (4)	−0.0059 (4)
C11	0.0217 (6)	0.0188 (5)	0.0232 (6)	0.0035 (4)	−0.0030 (4)	−0.0060 (4)
C12	0.0200 (6)	0.0261 (6)	0.0245 (6)	0.0002 (5)	−0.0009 (4)	−0.0059 (5)
C13	0.0191 (6)	0.0280 (6)	0.0283 (6)	0.0010 (5)	−0.0045 (5)	−0.0091 (5)
C14	0.0234 (6)	0.0442 (8)	0.0260 (6)	−0.0052 (5)	−0.0008 (5)	−0.0051 (6)
C15	0.0371 (8)	0.0470 (8)	0.0340 (7)	0.0094 (6)	−0.0083 (6)	−0.0120 (6)
C16	0.0232 (6)	0.0226 (6)	0.0217 (6)	0.0023 (4)	−0.0029 (4)	−0.0052 (4)
C17	0.0253 (6)	0.0272 (6)	0.0295 (6)	0.0028 (5)	−0.0109 (5)	−0.0087 (5)
C18	0.0218 (6)	0.0274 (6)	0.0342 (7)	0.0008 (5)	−0.0062 (5)	−0.0037 (5)
C19	0.0244 (6)	0.0292 (6)	0.0302 (7)	0.0038 (5)	−0.0073 (5)	−0.0030 (5)
C20	0.0618 (10)	0.0251 (7)	0.0514 (9)	0.0095 (7)	−0.0073 (8)	−0.0026 (6)
C21	0.0853 (14)	0.0385 (9)	0.0568 (11)	0.0231 (9)	−0.0111 (10)	−0.0145 (8)

S1—O3	1.4286 (10)	C7—H7	0.9300
S1—O2	1.4333 (9)	C8—C9	1.3762 (17)
S1—N1	1.6411 (10)	C8—C13	1.4247 (17)
S1—C5	1.7527 (13)	C9—C10	1.4212 (16)
O1—C9	1.3734 (14)	C10—C11	1.4213 (16)
O1—C14	1.4479 (16)	C11—C16	1.3900 (17)
O4—C2	1.3597 (17)	C11—C12	1.4115 (17)
O4—C1	1.4254 (19)	C12—C13	1.3602 (17)
O5—C19	1.1964 (16)	C12—H12	0.9300
O6—C19	1.3332 (16)	C13—H13	0.9300
O6—C20	1.4544 (17)	C14—C15	1.497 (2)
N1—C8	1.4271 (15)	C14—H14A	0.9700
N1—H1N	0.8817	C14—H14B	0.9700
N2—C10	1.3515 (15)	C15—H15A	0.9600
N2—N3	1.3557 (14)	C15—H15B	0.9600
N3—C16	1.3365 (15)	C15—H15C	0.9600
N3—C17	1.4595 (15)	C16—H16	0.9300
C1—H1A	0.9600	C17—C18	1.5139 (17)
C1—H1B	0.9600	C17—H17A	0.9700
C1—H1C	0.9600	C17—H17B	0.9700
C2—C3	1.3889 (19)	C18—C19	1.5038 (18)
C2—C7	1.393 (2)	C18—H18A	0.9700
C3—C4	1.385 (2)	C18—H18B	0.9700
C3—H3	0.9300	C20—C21	1.498 (2)
C4—C5	1.3843 (18)	C20—H20A	0.9700
C4—H4	0.9300	C20—H20B	0.9700
C5—C6	1.3884 (18)	C21—H21A	0.9600
C6—C7	1.373 (2)	C21—H21B	0.9600
C6—H6	0.9300	C21—H21C	0.9600
O3—S1—O2	118.61 (6)	C16—C11—C10	104.09 (10)
O3—S1—N1	108.67 (6)	C12—C11—C10	120.73 (11)
O2—S1—N1	105.11 (6)	C13—C12—C11	118.30 (11)
O3—S1—C5	107.80 (6)	C13—C12—H12	120.8
O2—S1—C5	109.22 (6)	C11—C12—H12	120.8
N1—S1—C5	106.87 (6)	C12—C13—C8	121.61 (11)
C9—O1—C14	115.21 (9)	C12—C13—H13	119.2
C2—O4—C1	118.54 (12)	C8—C13—H13	119.2
C19—O6—C20	116.37 (11)	O1—C14—C15	112.18 (11)
C8—N1—S1	122.30 (8)	O1—C14—H14A	109.2
C8—N1—H1N	115.2	C15—C14—H14A	109.2
S1—N1—H1N	107.6	O1—C14—H14B	109.2
C10—N2—N3	103.08 (9)	C15—C14—H14B	109.2
C16—N3—N2	114.45 (10)	H14A—C14—H14B	107.9
C16—N3—C17	127.11 (10)	C14—C15—H15A	109.5
N2—N3—C17	118.43 (10)	C14—C15—H15B	109.5
O4—C1—H1A	109.5	H15A—C15—H15B	109.5
O4—C1—H1B	109.5	C14—C15—H15C	109.5
H1A—C1—H1B	109.5	H15A—C15—H15C	109.5
O4—C1—H1C	109.5	H15B—C15—H15C	109.5
H1A—C1—H1C	109.5	N3—C16—C11	106.58 (10)
H1B—C1—H1C	109.5	N3—C16—H16	126.7
O4—C2—C3	124.55 (13)	C11—C16—H16	126.7
O4—C2—C7	115.06 (12)	N3—C17—C18	111.52 (10)
C3—C2—C7	120.38 (13)	N3—C17—H17A	109.3
C4—C3—C2	119.02 (12)	C18—C17—H17A	109.3
C4—C3—H3	120.5	N3—C17—H17B	109.3
C2—C3—H3	120.5	C18—C17—H17B	109.3
C5—C4—C3	120.42 (12)	H17A—C17—H17B	108.0
C5—C4—H4	119.8	C19—C18—C17	113.44 (10)
C3—C4—H4	119.8	C19—C18—H18A	108.9
C4—C5—C6	120.39 (12)	C17—C18—H18A	108.9
C4—C5—S1	120.29 (10)	C19—C18—H18B	108.9
C6—C5—S1	119.27 (10)	C17—C18—H18B	108.9
C7—C6—C5	119.51 (12)	H18A—C18—H18B	107.7
C7—C6—H6	120.2	O5—C19—O6	123.56 (12)
C5—C6—H6	120.2	O5—C19—C18	125.34 (12)
C6—C7—C2	120.27 (13)	O6—C19—C18	111.09 (11)
C6—C7—H7	119.9	O6—C20—C21	106.89 (13)
C2—C7—H7	119.9	O6—C20—H20A	110.3
C9—C8—C13	121.41 (11)	C21—C20—H20A	110.3
C9—C8—N1	117.62 (11)	O6—C20—H20B	110.3
C13—C8—N1	120.85 (11)	C21—C20—H20B	110.3
O1—C9—C8	119.24 (10)	H20A—C20—H20B	108.6
O1—C9—C10	122.63 (10)	C20—C21—H21A	109.5
C8—C9—C10	117.85 (10)	C20—C21—H21B	109.5
N2—C10—C9	128.11 (11)	H21A—C21—H21B	109.5
N2—C10—C11	111.80 (10)	C20—C21—H21C	109.5
C9—C10—C11	120.07 (11)	H21A—C21—H21C	109.5
C16—C11—C12	135.12 (11)	H21B—C21—H21C	109.5
O3—S1—N1—C8	61.31 (11)	N1—C8—C9—C10	175.02 (10)
O2—S1—N1—C8	−170.75 (9)	N3—N2—C10—C9	177.71 (11)
C5—S1—N1—C8	−54.76 (11)	N3—N2—C10—C11	−0.64 (12)
C10—N2—N3—C16	0.57 (13)	O1—C9—C10—N2	−3.11 (18)
C10—N2—N3—C17	−178.49 (10)	C8—C9—C10—N2	−176.86 (11)
C1—O4—C2—C3	1.4 (2)	O1—C9—C10—C11	175.13 (10)
C1—O4—C2—C7	−179.11 (13)	C8—C9—C10—C11	1.37 (16)
O4—C2—C3—C4	179.34 (13)	N2—C10—C11—C16	0.50 (13)
C7—C2—C3—C4	−0.1 (2)	C9—C10—C11—C16	−178.00 (10)
C2—C3—C4—C5	−0.5 (2)	N2—C10—C11—C12	178.30 (10)
C3—C4—C5—C6	0.5 (2)	C9—C10—C11—C12	−0.20 (16)
C3—C4—C5—S1	177.81 (10)	C16—C11—C12—C13	175.71 (13)
O3—S1—C5—C4	156.16 (10)	C10—C11—C12—C13	−1.27 (17)
O2—S1—C5—C4	26.04 (12)	C11—C12—C13—C8	1.56 (18)
N1—S1—C5—C4	−87.18 (11)	C9—C8—C13—C12	−0.36 (18)
O3—S1—C5—C6	−26.52 (12)	N1—C8—C13—C12	−176.38 (11)
O2—S1—C5—C6	−156.64 (10)	C9—O1—C14—C15	75.69 (14)
N1—S1—C5—C6	90.14 (11)	N2—N3—C16—C11	−0.27 (13)
C4—C5—C6—C7	0.0 (2)	C17—N3—C16—C11	178.69 (10)
S1—C5—C6—C7	−177.28 (11)	C12—C11—C16—N3	−177.46 (13)
C5—C6—C7—C2	−0.6 (2)	C10—C11—C16—N3	−0.14 (12)
O4—C2—C7—C6	−178.83 (13)	C16—N3—C17—C18	111.14 (13)
C3—C2—C7—C6	0.6 (2)	N2—N3—C17—C18	−69.93 (13)
S1—N1—C8—C9	141.07 (10)	N3—C17—C18—C19	−72.33 (14)
S1—N1—C8—C13	−42.76 (15)	C20—O6—C19—O5	−3.1 (2)
C14—O1—C9—C8	−123.84 (12)	C20—O6—C19—C18	175.71 (12)
C14—O1—C9—C10	62.49 (14)	C17—C18—C19—O5	−24.91 (19)
C13—C8—C9—O1	−175.09 (10)	C17—C18—C19—O6	156.26 (11)
N1—C8—C9—O1	1.05 (16)	C19—O6—C20—C21	178.54 (14)
C13—C8—C9—C10	−1.12 (17)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O2i	0.88	2.12	2.9779 (15)	164
C3—H3···O5ii	0.93	2.41	3.3277 (17)	168
C21—H21B···Cg1iii	0.93	2.98	3.6660 (18)	130

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the pyrazole ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯O2i	0.88	2.12	2.9779 (15)	164
C3—H3⋯O5ii	0.93	2.41	3.3277 (17)	168
C21—H21B⋯Cg1iii	0.93	2.98	3.6660 (18)	130

Symmetry codes: (i) ; (ii) ; (iii) .