N-(12-Amino-9,10-di­hydro-9,10-ethano­anthracen-11-yl)-4-methyl­benzene­sulfonamide

Mague, J.T.; Abdel-Aziz, A.A.-M.; El-Azab, A.S.; El-Sherbeny, M.A.

doi:10.1107/S1600536814002189

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 70| Part 3| March 2014| Pages o248-o249

doi:10.1107/S1600536814002189

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N-(12-Amino-9,10-dihydro-9,10-ethanoanthracen-11-yl)-4-methylbenzenesulfonamide

Joel T. Mague,^a ^* Alaa A.-M. Abdel-Aziz,^b,^c ‡ Adel S. El-Azab ^b,^d and Magda A. El-Sherbeny ^c

^aDepartment of Chemistry, Tulane University, New Orleans, LA 70118, USA, ^bDepartment of Pharmaceutical Chemistry, College of, Pharmacy, King Saud University, Riyadh 11451, Saudi Arabia, ^cDepartment of Medicinal Chemistry, Faculty of Pharmacy, University of Mansoura, Mansoura 35516, Egypt, and ^dDepartment of Organic Chemistry, Faculty of Pharmacy, Al-Azhar University, Cairo 11884, Egypt
^*Correspondence e-mail: joelt@tulane.edu

(Received 28 January 2014; accepted 29 January 2014; online 5 February 2014)

The title compound, C₂₃H₂₂N₂O₂S, crystallizes with the 4-methylbenzenesulfonamide entity oriented towards the center of the bridgehead C atoms with a C—N—S—C torsion angle of −61.3 (2)°. The molecule features an intramolecular N—H⋯N hydrogen bond. Weak C—H⋯O and C—H⋯π interactions aid in forming the three-dimensional supramolecular structure.

CCDC reference: 984234

Related literature

For chiral ligand devlopment, see: Abdel-Aziz et al. (2000 , 2001 , 2004 ); Matsunaga et al. (2005 ); Seo et al. (2001 ). For similar compounds and applications, see: Yamakuchi et al. (2005 ); Matsunaga et al. (2005); Abdel-Aziz et al. (2004). For the synthesis of the title compound, see: Matsunaga et al. (2005).

Experimental

Crystal data

C₂₃H₂₂N₂O₂S
M_r = 390.49
Monoclinic, P 2₁
a = 8.9362 (2) Å
b = 6.8766 (2) Å
c = 15.5039 (4) Å
β = 91.540 (1)°
V = 952.38 (4) Å³
Z = 2
Cu Kα radiation
μ = 1.68 mm⁻¹
T = 100 K
0.25 × 0.13 × 0.03 mm

Data collection

Bruker D8 VENTURE PHOTON 100 CMOS diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2012 ) T_min = 0.83, T_max = 0.95
16018 measured reflections
3531 independent reflections
3255 reflections with I > 2σ(I)
R_int = 0.035

Refinement

R[F² > 2σ(F²)] = 0.028
wR(F²) = 0.066
S = 1.07
3531 reflections
282 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.17 e Å⁻³
Δρ_min = −0.21 e Å⁻³
Absolute structure: Flack (1983 ), 1582 Friedel pairs
Absolute structure parameter: 0.036 (13)

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C3–C8 benzene ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯N2	0.90 (2)	2.04 (2)	2.592 (2)	117.9 (17)
C11—H11⋯Cg1ⁱ	0.95	2.87	3.712 (2)	149
C5—H5⋯O1ⁱⁱ	0.95	2.58	3.269 (2)	129
C12—H12⋯O1ⁱⁱⁱ	0.95	2.52	3.446 (2)	166
C23—H23A⋯O1^iv	0.98	2.51	3.259 (3)	133
Symmetry codes: (i) $[-x, y-{\script{1\over 2}}, -z+1]$ ; (ii) x-1, y+1, z; (iii) $[-x+1, y+{\script{1\over 2}}, -z+1]$ ; (iv) $[-x+1, y-{\script{1\over 2}}, -z]$ .

Data collection: APEX2 (Bruker, 2012); cell refinement: SAINT (Bruker, 2012); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: DIAMOND (Brandenburg & Putz, 2012 ); software used to prepare material for publication: SHELXTL (Bruker, 2012).

Supporting information

CCDC reference: 984234

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536814002189/tk5292sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536814002189/tk5292Isup2.hkl

checkCIF report

Experimental top

Synthesis and crystallization top

The title compound was prepared by the literature method (Matsunaga et al., 2005) and recrystallized from CH₂Cl₂/EtOH as colourless plates.

Refinement top

H-atoms attached to the bridgehead carbon atoms and to nitrogen were located and refined. The remainder were placed in calculated positions (C—H = 0.95 - 0.98 Å) and included as riding contributions with isotropic displacement parameters 1.2–1.5 times those of the attached carbon atoms.

Results and discussion top

The development of chiral ligands for asymmetric catalytic reactions is a subject of considerable interest in the field of asymmetric synthesis (Abdel-Aziz et al., 2000, 2001, 2004; Matsunaga et al., 2005; Seo et al., 2001). As part of our onging program of drug design and discovery we report the structure of the title compound. Some applications of related compounds have been reported (Yamakuchi et al., 2005; Matsunaga et al., 2005; Abdel-Aziz et al., 2004). The 4-methylbenzenesulfonamide entity is oriented towards the center of the bridgehead carbon atoms (C1, C16), partly due to the N1—H1N···N2 interaction, as indicated by the C1—N1—S1—C17 torsion angle of -61.3 (2)°. The dihedral angle between the benzene ring (C17–C22) and the mean plane of the C1/C2/C9/C16 unit is 87.78 (7)°. The packing of the molecules is aided by weak C—H···O hydrogen bonds as well as a C—H···π interaction between C11—H11 and the centroid of the C3–C8 ring at -x, -0.5 + y, 1 - z forming the three-dimensional supramolecular structure (Table 1 and Fig. 2).

Related literature top

For chiral ligand devlopment, see: Abdel-Aziz et al. (2000, 2001, 2004); Matsunaga et al. (2005); Seo et al. (2001). For similar compounds and applications, see: Yamakuchi et al. (2005); Matsunaga et al. (2005); Abdel-Aziz et al. (2004). For the synthesis of the title compound, see: Matsunaga et al. (2005).

Computing details top

Data collection: APEX2 (Bruker, 2012); cell refinement: SAINT (Bruker, 2012); data reduction: SAINT (Bruker, 2012); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: DIAMOND (Brandenburg & Putz, 2012); software used to prepare material for publication: SHELXTL (Bruker, 2012).

Figures top

	Fig. 1. Perspective view of the title molecule showing the intramolecular hydrogen bond. Displacement ellipsoids are drawn at the 50% probability level.
	Fig. 2. Packing diagram viewed down b with intermolecular interactions shown as dotted lines (C—H···O, purple; C—H···π, green).

N-(12-Amino-9,10-dihydro-9,10-ethanoanthracen-11-yl)-4-methylbenzenesulfonamide top

Crystal data top

C₂₃H₂₂N₂O₂S	F(000) = 412
M_r = 390.49	D_x = 1.362 Mg m⁻³
Monoclinic, P2₁	Cu Kα radiation, λ = 1.54178 Å
a = 8.9362 (2) Å	Cell parameters from 9974 reflections
b = 6.8766 (2) Å	θ = 2.9–69.8°
c = 15.5039 (4) Å	µ = 1.68 mm⁻¹
β = 91.540 (1)°	T = 100 K
V = 952.38 (4) Å³	Plate, colourless
Z = 2	0.25 × 0.13 × 0.03 mm

Data collection top

Bruker D8 VENTURE PHOTON 100 CMOS diffractometer	3531 independent reflections
Radiation source: INCOATEC IµS micro-focus source	3255 reflections with I > 2σ(I)
Mirror monochromator	R_int = 0.035
Detector resolution: 10.4167 pixels mm^-1	θ_max = 69.8°, θ_min = 2.9°
ω scans	h = −10→10
Absorption correction: multi-scan (SADABS; Bruker, 2012)	k = −8→8
T_min = 0.83, T_max = 0.95	l = −18→18
16018 measured reflections

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.028	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.066	w = 1/[σ²(F_o²) + (0.0302P)² + 0.1321P] where P = (F_o² + 2F_c²)/3
S = 1.07	(Δ/σ)_max = 0.001
3531 reflections	Δρ_max = 0.17 e Å⁻³
282 parameters	Δρ_min = −0.21 e Å⁻³
1 restraint	Absolute structure: Flack (1983), 1582 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.036 (13)

Crystal data top

C₂₃H₂₂N₂O₂S	V = 952.38 (4) Å³
M_r = 390.49	Z = 2
Monoclinic, P2₁	Cu Kα radiation
a = 8.9362 (2) Å	µ = 1.68 mm⁻¹
b = 6.8766 (2) Å	T = 100 K
c = 15.5039 (4) Å	0.25 × 0.13 × 0.03 mm
β = 91.540 (1)°

Data collection top

Bruker D8 VENTURE PHOTON 100 CMOS diffractometer	3531 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2012)	3255 reflections with I > 2σ(I)
T_min = 0.83, T_max = 0.95	R_int = 0.035
16018 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.028	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.066	Δρ_max = 0.17 e Å⁻³
S = 1.07	Δρ_min = −0.21 e Å⁻³
3531 reflections	Absolute structure: Flack (1983), 1582 Friedel pairs
282 parameters	Absolute structure parameter: 0.036 (13)
1 restraint

Special details top

Experimental. The diffraction data were obtained from 8 sets of 340 frames, each of width 0.5° in ω, collected at φ = 0.00, 90.00, 180.00 and 270.00° and at 2θ = -50.00 and -90.00° and 4 sets of 340 frames, each of width 0.5° in ω collected at 2θ = -90.00° and φ = 45.00, 135.00, 225.00 and 315.00°. The scan time was 20 sec/frame.

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. H-atoms attached to the bridgehead carbon atoms and to nitrogen were located and refined. The remainder were placed in calculated positions (C—H = 0.95 - 0.98 Å) and included as riding contributions with isotropic displacement parameters 1.2 - 1.5 times those of the attached carbon atoms.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
S1	0.47223 (4)	0.59364 (7)	0.19075 (3)	0.02581 (11)
O1	0.60539 (14)	0.4887 (2)	0.21492 (8)	0.0344 (3)
O2	0.48013 (14)	0.79099 (19)	0.16197 (8)	0.0314 (3)
N1	0.36963 (15)	0.5913 (3)	0.27530 (9)	0.0254 (3)
H1N	0.370 (2)	0.473 (3)	0.3000 (13)	0.036 (6)*
N2	0.19878 (19)	0.4067 (2)	0.38013 (13)	0.0310 (4)
H2A	0.149 (3)	0.296 (4)	0.3825 (16)	0.053 (7)*
H2B	0.228 (2)	0.440 (3)	0.4308 (15)	0.036 (6)*
C1	0.21944 (19)	0.6768 (3)	0.27202 (12)	0.0239 (4)
H1	0.1753 (18)	0.667 (3)	0.2111 (11)	0.020 (5)*
C2	0.22327 (19)	0.8966 (3)	0.29742 (11)	0.0223 (4)
H2	0.295 (2)	0.963 (3)	0.2608 (12)	0.024 (5)*
C3	0.06161 (19)	0.9626 (2)	0.28635 (11)	0.0213 (4)
C4	0.00777 (18)	1.1038 (3)	0.22989 (10)	0.0253 (4)
H4	0.0742	1.1748	0.1949	0.03*
C5	−0.1461 (2)	1.1400 (3)	0.22537 (11)	0.0276 (4)
H5	−0.1842	1.2399	0.1886	0.033*
C6	−0.2433 (2)	1.0319 (3)	0.27387 (12)	0.0280 (4)
H6	−0.348	1.0544	0.2683	0.034*
C7	−0.18973 (19)	0.8909 (3)	0.33066 (12)	0.0252 (4)
H7	−0.257	0.8172	0.364	0.03*
C8	−0.03595 (19)	0.8586 (2)	0.33827 (11)	0.0224 (4)
C9	0.04146 (19)	0.7098 (3)	0.39548 (12)	0.0229 (4)
H9	−0.0255 (19)	0.644 (3)	0.4339 (11)	0.021 (5)*
C10	0.16898 (18)	0.8096 (2)	0.44541 (11)	0.0208 (4)
C11	0.1950 (2)	0.8058 (3)	0.53355 (11)	0.0246 (4)
H11	0.1301	0.7354	0.5697	0.03*
C12	0.3175 (2)	0.9060 (3)	0.56923 (11)	0.0254 (4)
H12	0.3357	0.9047	0.6299	0.03*
C13	0.41273 (19)	1.0076 (3)	0.51641 (12)	0.0254 (4)
H13	0.4947	1.0779	0.5412	0.03*
C14	0.38929 (19)	1.0075 (3)	0.42748 (12)	0.0232 (4)
H14	0.4565	1.0744	0.3914	0.028*
C15	0.26676 (18)	0.9089 (2)	0.39163 (11)	0.0208 (4)
C16	0.1156 (2)	0.5601 (3)	0.33479 (12)	0.0258 (4)
H16	0.0421 (19)	0.500 (3)	0.2966 (11)	0.016 (4)*
C17	0.37770 (19)	0.4609 (3)	0.10866 (11)	0.0242 (4)
C18	0.4012 (2)	0.2615 (3)	0.10068 (12)	0.0299 (4)
H18	0.47	0.1958	0.1383	0.036*
C19	0.3221 (2)	0.1610 (3)	0.03665 (13)	0.0366 (5)
H19	0.338	0.0251	0.0306	0.044*
C20	0.2202 (2)	0.2533 (3)	−0.01897 (12)	0.0346 (5)
C21	0.1995 (2)	0.4513 (3)	−0.00981 (12)	0.0352 (5)
H21	0.1302	0.5167	−0.0472	0.042*
C22	0.2777 (2)	0.5561 (3)	0.05282 (12)	0.0315 (4)
H22	0.2632	0.6925	0.0577	0.038*
C23	0.1345 (3)	0.1440 (4)	−0.08860 (15)	0.0525 (7)
H23A	0.1836	0.1615	−0.1438	0.079*
H23B	0.0319	0.1941	−0.0932	0.079*
H23C	0.1322	0.0054	−0.074	0.079*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0225 (2)	0.0273 (2)	0.0275 (2)	0.0056 (2)	−0.00269 (16)	−0.0029 (2)
O1	0.0248 (7)	0.0437 (8)	0.0345 (7)	0.0115 (6)	−0.0042 (5)	−0.0040 (6)
O2	0.0285 (7)	0.0281 (7)	0.0377 (7)	−0.0004 (6)	−0.0011 (6)	−0.0022 (6)
N1	0.0255 (7)	0.0255 (8)	0.0250 (7)	0.0081 (8)	−0.0050 (6)	−0.0017 (8)
N2	0.0301 (9)	0.0185 (8)	0.0440 (11)	0.0015 (7)	−0.0045 (8)	0.0020 (8)
C1	0.0222 (9)	0.0221 (8)	0.0270 (10)	0.0063 (8)	−0.0060 (8)	−0.0029 (8)
C2	0.0213 (9)	0.0206 (9)	0.0249 (9)	0.0007 (7)	−0.0010 (7)	−0.0006 (7)
C3	0.0229 (9)	0.0188 (9)	0.0221 (9)	0.0036 (7)	−0.0037 (7)	−0.0054 (7)
C4	0.0286 (9)	0.0226 (8)	0.0244 (8)	0.0038 (9)	−0.0022 (7)	−0.0028 (9)
C5	0.0338 (10)	0.0244 (10)	0.0241 (9)	0.0094 (8)	−0.0068 (8)	−0.0024 (7)
C6	0.0243 (9)	0.0288 (10)	0.0304 (10)	0.0078 (8)	−0.0058 (8)	−0.0068 (8)
C7	0.0233 (9)	0.0224 (9)	0.0298 (10)	0.0002 (7)	−0.0024 (7)	−0.0058 (8)
C8	0.0230 (9)	0.0195 (9)	0.0242 (9)	−0.0003 (7)	−0.0053 (7)	−0.0051 (7)
C9	0.0211 (9)	0.0194 (9)	0.0283 (10)	−0.0017 (7)	0.0001 (8)	0.0016 (7)
C10	0.0199 (8)	0.0152 (8)	0.0271 (10)	0.0028 (7)	−0.0019 (7)	0.0003 (7)
C11	0.0262 (9)	0.0194 (9)	0.0283 (10)	0.0053 (7)	0.0023 (7)	0.0032 (7)
C12	0.0302 (10)	0.0229 (9)	0.0226 (9)	0.0070 (8)	−0.0061 (7)	−0.0026 (7)
C13	0.0227 (9)	0.0187 (8)	0.0343 (10)	0.0034 (7)	−0.0078 (8)	−0.0058 (8)
C14	0.0208 (9)	0.0175 (8)	0.0311 (9)	0.0022 (7)	−0.0012 (7)	−0.0003 (7)
C15	0.0198 (8)	0.0154 (8)	0.0270 (9)	0.0050 (7)	−0.0014 (7)	−0.0013 (7)
C16	0.0229 (9)	0.0193 (10)	0.0347 (10)	0.0000 (7)	−0.0070 (7)	−0.0028 (8)
C17	0.0237 (9)	0.0275 (10)	0.0216 (9)	0.0007 (8)	0.0027 (7)	−0.0010 (8)
C18	0.0323 (11)	0.0269 (10)	0.0305 (10)	0.0032 (8)	0.0039 (8)	0.0019 (9)
C19	0.0434 (12)	0.0263 (10)	0.0407 (12)	−0.0041 (9)	0.0135 (10)	−0.0067 (9)
C20	0.0315 (11)	0.0439 (12)	0.0287 (10)	−0.0074 (9)	0.0082 (8)	−0.0082 (9)
C21	0.0342 (11)	0.0448 (13)	0.0265 (10)	−0.0002 (10)	−0.0030 (8)	−0.0008 (9)
C22	0.0343 (10)	0.0309 (11)	0.0291 (10)	0.0044 (8)	−0.0022 (8)	0.0010 (8)
C23	0.0447 (12)	0.0670 (19)	0.0459 (13)	−0.0138 (12)	0.0058 (10)	−0.0235 (12)

Geometric parameters (Å, º) top

S1—O2	1.4309 (14)	C9—C16	1.555 (3)
S1—O1	1.4328 (13)	C9—H9	0.968 (18)
S1—N1	1.6197 (15)	C10—C11	1.380 (2)
S1—C17	1.7631 (18)	C10—C15	1.401 (2)
N1—C1	1.465 (2)	C11—C12	1.395 (3)
N1—H1N	0.90 (2)	C11—H11	0.95
N2—C16	1.460 (2)	C12—C13	1.386 (3)
N2—H2A	0.88 (3)	C12—H12	0.95
N2—H2B	0.85 (2)	C13—C14	1.389 (2)
C1—C2	1.562 (2)	C13—H13	0.95
C1—C16	1.581 (3)	C14—C15	1.391 (2)
C1—H1	1.015 (17)	C14—H14	0.95
C2—C15	1.504 (2)	C16—H16	0.967 (17)
C2—C3	1.520 (2)	C17—C22	1.391 (2)
C2—H2	0.982 (19)	C17—C18	1.393 (3)
C3—C4	1.385 (3)	C18—C19	1.388 (3)
C3—C8	1.399 (3)	C18—H18	0.95
C4—C5	1.397 (2)	C19—C20	1.390 (3)
C4—H4	0.95	C19—H19	0.95
C5—C6	1.381 (3)	C20—C21	1.382 (3)
C5—H5	0.95	C20—C23	1.508 (3)
C6—C7	1.386 (3)	C21—C22	1.384 (3)
C6—H6	0.95	C21—H21	0.95
C7—C8	1.394 (2)	C22—H22	0.95
C7—H7	0.95	C23—H23A	0.98
C8—C9	1.510 (2)	C23—H23B	0.98
C9—C10	1.524 (2)	C23—H23C	0.98

O2—S1—O1	120.76 (9)	C11—C10—C15	120.47 (16)
O2—S1—N1	107.20 (9)	C11—C10—C9	126.75 (16)
O1—S1—N1	105.51 (8)	C15—C10—C9	112.76 (15)
O2—S1—C17	107.00 (8)	C10—C11—C12	119.52 (17)
O1—S1—C17	107.86 (8)	C10—C11—H11	120.2
N1—S1—C17	107.96 (8)	C12—C11—H11	120.2
C1—N1—S1	120.39 (12)	C13—C12—C11	120.17 (16)
C1—N1—H1N	111.6 (13)	C13—C12—H12	119.9
S1—N1—H1N	111.1 (13)	C11—C12—H12	119.9
C16—N2—H2A	113.1 (16)	C12—C13—C14	120.51 (16)
C16—N2—H2B	113.2 (16)	C12—C13—H13	119.7
H2A—N2—H2B	109 (2)	C14—C13—H13	119.7
N1—C1—C2	111.46 (14)	C13—C14—C15	119.52 (17)
N1—C1—C16	109.09 (14)	C13—C14—H14	120.2
C2—C1—C16	110.19 (15)	C15—C14—H14	120.2
N1—C1—H1	109.8 (10)	C14—C15—C10	119.77 (16)
C2—C1—H1	107.7 (10)	C14—C15—C2	126.55 (16)
C16—C1—H1	108.6 (10)	C10—C15—C2	113.69 (15)
C15—C2—C3	108.25 (14)	N2—C16—C9	113.99 (15)
C15—C2—C1	107.61 (14)	N2—C16—C1	111.32 (14)
C3—C2—C1	104.26 (14)	C9—C16—C1	107.66 (14)
C15—C2—H2	112.3 (11)	N2—C16—H16	108.2 (11)
C3—C2—H2	115.5 (11)	C9—C16—H16	111.2 (10)
C1—C2—H2	108.3 (11)	C1—C16—H16	104.0 (10)
C4—C3—C8	120.72 (16)	C22—C17—C18	120.25 (17)
C4—C3—C2	126.44 (16)	C22—C17—S1	119.53 (14)
C8—C3—C2	112.80 (15)	C18—C17—S1	120.20 (14)
C3—C4—C5	118.77 (17)	C19—C18—C17	118.60 (18)
C3—C4—H4	120.6	C19—C18—H18	120.7
C5—C4—H4	120.6	C17—C18—H18	120.7
C6—C5—C4	120.62 (16)	C18—C19—C20	121.91 (18)
C6—C5—H5	119.7	C18—C19—H19	119.0
C4—C5—H5	119.7	C20—C19—H19	119.0
C5—C6—C7	120.72 (17)	C21—C20—C19	118.26 (18)
C5—C6—H6	119.6	C21—C20—C23	119.9 (2)
C7—C6—H6	119.6	C19—C20—C23	121.9 (2)
C6—C7—C8	119.20 (17)	C20—C21—C22	121.26 (19)
C6—C7—H7	120.4	C20—C21—H21	119.4
C8—C7—H7	120.4	C22—C21—H21	119.4
C7—C8—C3	119.86 (16)	C21—C22—C17	119.70 (18)
C7—C8—C9	126.36 (16)	C21—C22—H22	120.2
C3—C8—C9	113.69 (15)	C17—C22—H22	120.2
C8—C9—C10	108.52 (14)	C20—C23—H23A	109.5
C8—C9—C16	106.81 (14)	C20—C23—H23B	109.5
C10—C9—C16	106.30 (14)	H23A—C23—H23B	109.5
C8—C9—H9	113.4 (10)	C20—C23—H23C	109.5
C10—C9—H9	111.4 (10)	H23A—C23—H23C	109.5
C16—C9—H9	110.0 (11)	H23B—C23—H23C	109.5

O2—S1—N1—C1	53.66 (16)	C12—C13—C14—C15	1.8 (3)
O1—S1—N1—C1	−176.43 (14)	C13—C14—C15—C10	−0.4 (2)
C17—S1—N1—C1	−61.31 (17)	C13—C14—C15—C2	178.89 (16)
S1—N1—C1—C2	−90.01 (17)	C11—C10—C15—C14	−1.3 (2)
S1—N1—C1—C16	148.09 (14)	C9—C10—C15—C14	−179.93 (15)
N1—C1—C2—C15	−67.85 (18)	C11—C10—C15—C2	179.27 (15)
C16—C1—C2—C15	53.41 (18)	C9—C10—C15—C2	0.7 (2)
N1—C1—C2—C3	177.35 (14)	C3—C2—C15—C14	−126.01 (18)
C16—C1—C2—C3	−61.39 (17)	C1—C2—C15—C14	121.86 (18)
C15—C2—C3—C4	127.49 (18)	C3—C2—C15—C10	53.35 (19)
C1—C2—C3—C4	−118.15 (18)	C1—C2—C15—C10	−58.78 (18)
C15—C2—C3—C8	−54.95 (19)	C8—C9—C16—N2	178.79 (14)
C1—C2—C3—C8	59.40 (18)	C10—C9—C16—N2	63.07 (19)
C8—C3—C4—C5	−0.3 (2)	C8—C9—C16—C1	54.78 (16)
C2—C3—C4—C5	177.07 (16)	C10—C9—C16—C1	−60.94 (17)
C3—C4—C5—C6	−2.4 (3)	N1—C1—C16—N2	2.1 (2)
C4—C5—C6—C7	2.7 (3)	C2—C1—C16—N2	−120.58 (16)
C5—C6—C7—C8	−0.2 (3)	N1—C1—C16—C9	127.70 (15)
C6—C7—C8—C3	−2.6 (3)	C2—C1—C16—C9	5.03 (18)
C6—C7—C8—C9	−178.97 (16)	O2—S1—C17—C22	−25.90 (17)
C4—C3—C8—C7	2.8 (3)	O1—S1—C17—C22	−157.23 (14)
C2—C3—C8—C7	−174.90 (15)	N1—S1—C17—C22	89.20 (16)
C4—C3—C8—C9	179.66 (15)	O2—S1—C17—C18	155.12 (14)
C2—C3—C8—C9	1.9 (2)	O1—S1—C17—C18	23.79 (17)
C7—C8—C9—C10	−131.40 (18)	N1—S1—C17—C18	−89.78 (16)
C3—C8—C9—C10	52.0 (2)	C22—C17—C18—C19	−0.5 (3)
C7—C8—C9—C16	114.37 (19)	S1—C17—C18—C19	178.43 (13)
C3—C8—C9—C16	−62.23 (18)	C17—C18—C19—C20	−0.3 (3)
C8—C9—C10—C11	127.94 (18)	C18—C19—C20—C21	0.6 (3)
C16—C9—C10—C11	−117.50 (18)	C18—C19—C20—C23	179.92 (19)
C8—C9—C10—C15	−53.57 (19)	C19—C20—C21—C22	0.1 (3)
C16—C9—C10—C15	60.99 (18)	C23—C20—C21—C22	−179.28 (19)
C15—C10—C11—C12	1.8 (2)	C20—C21—C22—C17	−0.9 (3)
C9—C10—C11—C12	−179.86 (16)	C18—C17—C22—C21	1.2 (3)
C10—C11—C12—C13	−0.4 (3)	S1—C17—C22—C21	−177.80 (15)
C11—C12—C13—C14	−1.3 (3)

Hydrogen-bond geometry (Å, º) top

Cg1 is the centroid of the C3–C8 benzene ring.

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···N2	0.90 (2)	2.04 (2)	2.592 (2)	117.9 (17)
C11—H11···Cg1ⁱ	0.95	2.87	3.712 (2)	149
C5—H5···O1ⁱⁱ	0.95	2.58	3.269 (2)	129
C12—H12···O1ⁱⁱⁱ	0.95	2.52	3.446 (2)	166
C23—H23A···O1^iv	0.98	2.51	3.259 (3)	133

Symmetry codes: (i) −x, y−1/2, −z+1; (ii) x−1, y+1, z; (iii) −x+1, y+1/2, −z+1; (iv) −x+1, y−1/2, −z.

Hydrogen-bond geometry (Å, º) top

Cg1 is the centroid of the C3–C8 benzene ring.

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···N2	0.90 (2)	2.04 (2)	2.592 (2)	117.9 (17)
C11—H11···Cg1ⁱ	0.95	2.87	3.712 (2)	149
C5—H5···O1ⁱⁱ	0.95	2.58	3.269 (2)	129
C12—H12···O1ⁱⁱⁱ	0.95	2.52	3.446 (2)	166
C23—H23A···O1^iv	0.98	2.51	3.259 (3)	133

Symmetry codes: (i) −x, y−1/2, −z+1; (ii) x−1, y+1, z; (iii) −x+1, y+1/2, −z+1; (iv) −x+1, y−1/2, −z.

Footnotes

‡Additional correspondence author, e-mail: alaa_moenes@yahoo.com.

Acknowledgements

The authors extend their appreciation to the Research Center of Pharmacy, King Saud University, for funding this work. JTM thanks the Tulane Chemistry Department for support of the Tulane Crystallography Laboratory and NSF–MRI grant No. 1228232 for the purchase of the diffractometer.

References

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Volume 70| Part 3| March 2014| Pages o248-o249

doi:10.1107/S1600536814002189

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N-(12-Amino-9,10-di­hydro-9,10-ethano­anthracen-11-yl)-4-methyl­benzene­sulfonamide

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N-(12-Amino-9,10-dihydro-9,10-ethanoanthracen-11-yl)-4-methylbenzenesulfonamide