4-Fluoro-N-methyl-N-(1,2,3,4-tetra­hydro­carbazol-3-yl)benzene­sulfonamide

Rasmussen, K.G.; Ulven, T.; Bond, A.D.

doi:10.1107/S160053680900840X

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 65| Part 4| April 2009| Page o742

doi:10.1107/S160053680900840X

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4-Fluoro-N-methyl-N-(1,2,3,4-tetrahydrocarbazol-3-yl)benzenesulfonamide

Kaspar Gothardt Rasmussen,^a Trond Ulven ^a and Andrew D. Bond ^a ^*

^aUniversity of Southern Denmark, Department of Physics and Chemistry, Campusvej 55, 5230 Odense M, Denmark
^*Correspondence e-mail: adb@chem.sdu.dk

(Received 3 March 2009; accepted 7 March 2009; online 11 March 2009)

In the title compound, C₁₉H₁₉FN₂O₂S, the hydrogenated six-membered ring of the carbazole unit adopts a half-chair conformation and the plane of the fluorophenyl ring forms a dihedral angle of 41.5 (1)° with respect to the carbazole mean plane. The crystal structure is segregated into layers containing the carbazole units and fluorophenyl rings in alternate (200) planes. The carbazole units form centrosymmetric face-to-face interactions [interplanar separation = 4.06 (1) Å] and edge-to-face interactions in which the N—H group is directed towards an adjacent carbazole face, with a shortest H⋯C contact of 2.53 Å. The fluorophenyl rings form face-to-face contacts with an approximate interplanar separation of 3.75 Å and a centroid–centroid distance of 4.73 (1) Å.

Related literature

For background literature and synthesis details, see: Ulven & Kostenis (2005 , 2006 ). For related structures, see: Bjerrum et al. (2009 ); Löffler et al. (2009 ).

Experimental

Crystal data

C₁₉H₁₉FN₂O₂S
M_r = 358.42
Monoclinic, P 2₁ /c
a = 15.2748 (7) Å
b = 12.0319 (6) Å
c = 9.4430 (4) Å
β = 102.445 (2)°
V = 1694.70 (14) Å³
Z = 4
Mo Kα radiation
μ = 0.22 mm⁻¹
T = 180 K
0.20 × 0.20 × 0.08 mm

Data collection

Bruker–Nonius X8 APEX-II CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 2003 ) T_min = 0.870, T_max = 0.983
29053 measured reflections
4157 independent reflections
2816 reflections with I > 2σ(I)
R_int = 0.039

Refinement

R[F² > 2σ(F²)] = 0.039
wR(F²) = 0.100
S = 1.03
4157 reflections
227 parameters
H-atom parameters constrained
Δρ_max = 0.28 e Å⁻³
Δρ_min = −0.36 e Å⁻³

Data collection: APEX2 (Bruker, 2004 ); cell refinement: SAINT (Bruker, 2003 ); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S160053680900840X/gk2196sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S160053680900840X/gk2196Isup2.hkl

checkCIF report

Comment top

The title compound is useful as an intermediate in the synthesis of antagonists of the prostaglandin D₂ receptor CRTH2 (DP₂) (Ulven & Kostenis, 2006).

Related literature top

For background literature and synthesis details, see: Ulven & Kostenis (2005, 2006). For related structures, see: Bjerrum et al. (2009); Löffler et al. (2009).

Experimental top

The compound was synthesized as described in Ulven & Kostenis (2005).

Computing details top

Data collection: APEX2 (Bruker, 2004); cell refinement: SAINT (Bruker, 2003); data reduction: SAINT (Bruker, 2003); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

	Fig. 1. Molecular structure of the title compound with displacement ellipsoids shown at 50% probability for non-H atoms.
	Fig. 2. Unit-cell contents projected along the b axis, showing segregation of carbazole and fluorophenyl groups in the (200) planes. H atoms are omitted.

4-Fluoro-N-methyl-N-(1,2,3,4- tetrahydrocarbazol-3-yl)benzenesulfonamide top

Crystal data top

C₁₉H₁₉FN₂O₂S	F(000) = 752
M_r = 358.42	D_x = 1.405 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 6906 reflections
a = 15.2748 (7) Å	θ = 2.8–24.2°
b = 12.0319 (6) Å	µ = 0.22 mm⁻¹
c = 9.4430 (4) Å	T = 180 K
β = 102.445 (2)°	Plate, yellow
V = 1694.70 (14) Å³	0.20 × 0.20 × 0.08 mm
Z = 4

Data collection top

Bruker–Nonius X8 APEX-II CCD diffractometer	4157 independent reflections
Radiation source: fine-focus sealed tube	2816 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.039
Thin–slice ω and ϕ scans	θ_max = 28.4°, θ_min = 3.6°
Absorption correction: multi-scan (SADABS; Sheldrick, 2003)	h = −20→20
T_min = 0.870, T_max = 0.983	k = −14→16
29053 measured reflections	l = −12→12

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)] = 0.039	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.100	H-atom parameters constrained
S = 1.03	w = 1/[σ²(F_o²) + (0.0499P)² + 0.197P] where P = (F_o² + 2F_c²)/3
4157 reflections	(Δ/σ)_max = 0.001
227 parameters	Δρ_max = 0.28 e Å⁻³
0 restraints	Δρ_min = −0.36 e Å⁻³

Crystal data top

C₁₉H₁₉FN₂O₂S	V = 1694.70 (14) Å³
M_r = 358.42	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 15.2748 (7) Å	µ = 0.22 mm⁻¹
b = 12.0319 (6) Å	T = 180 K
c = 9.4430 (4) Å	0.20 × 0.20 × 0.08 mm
β = 102.445 (2)°

Data collection top

Bruker–Nonius X8 APEX-II CCD diffractometer	4157 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 2003)	2816 reflections with I > 2σ(I)
T_min = 0.870, T_max = 0.983	R_int = 0.039
29053 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.039	0 restraints
wR(F²) = 0.100	H-atom parameters constrained
S = 1.03	Δρ_max = 0.28 e Å⁻³
4157 reflections	Δρ_min = −0.36 e Å⁻³
227 parameters

Special details top

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.

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

	x	y	z	U_iso*/U_eq
S1	0.18551 (2)	0.58771 (3)	0.65744 (4)	0.03103 (13)
F1	−0.04364 (7)	0.90794 (10)	0.28602 (13)	0.0644 (4)
O11	0.23235 (7)	0.64670 (9)	0.78251 (11)	0.0366 (3)
O12	0.13016 (7)	0.49488 (9)	0.67472 (12)	0.0418 (3)
N1	0.58988 (8)	0.75139 (11)	0.61606 (14)	0.0345 (3)
H1	0.6060	0.8092	0.5706	0.041*
N2	0.26020 (8)	0.54273 (11)	0.57403 (14)	0.0332 (3)
C1	0.64139 (10)	0.70104 (13)	0.73606 (16)	0.0310 (4)
C2	0.72812 (10)	0.72533 (15)	0.81236 (18)	0.0392 (4)
H2A	0.7609	0.7863	0.7862	0.047*
C3	0.76405 (11)	0.65708 (16)	0.92717 (19)	0.0440 (5)
H3A	0.8230	0.6713	0.9813	0.053*
C4	0.71637 (11)	0.56773 (15)	0.96612 (18)	0.0417 (4)
H4A	0.7435	0.5220	1.0455	0.050*
C5	0.63012 (10)	0.54441 (14)	0.89130 (17)	0.0346 (4)
H5A	0.5979	0.4836	0.9191	0.041*
C6	0.59115 (9)	0.61180 (12)	0.77416 (16)	0.0275 (3)
C7	0.50635 (10)	0.61190 (12)	0.67235 (15)	0.0260 (3)
C8	0.42395 (9)	0.54333 (13)	0.66823 (16)	0.0295 (3)
H8A	0.4162	0.5289	0.7680	0.035*
H8B	0.4294	0.4711	0.6208	0.035*
C9	0.34359 (10)	0.60775 (13)	0.58295 (16)	0.0285 (4)
H9A	0.3378	0.6767	0.6393	0.034*
C10	0.35930 (11)	0.64426 (13)	0.43638 (17)	0.0348 (4)
H10A	0.3036	0.6771	0.3784	0.042*
H10B	0.3749	0.5788	0.3833	0.042*
C11	0.43474 (10)	0.72944 (13)	0.45470 (17)	0.0351 (4)
H11A	0.4576	0.7338	0.3644	0.042*
H11B	0.4116	0.8037	0.4734	0.042*
C12	0.50906 (10)	0.69691 (13)	0.57835 (16)	0.0283 (3)
C13	0.23280 (12)	0.46523 (15)	0.45307 (19)	0.0449 (5)
H13A	0.2834	0.4171	0.4458	0.067*
H13B	0.2138	0.5071	0.3627	0.067*
H13C	0.1829	0.4195	0.4698	0.067*
C14	0.11647 (9)	0.68484 (13)	0.54524 (16)	0.0297 (4)
C15	0.04708 (10)	0.64712 (15)	0.43564 (18)	0.0390 (4)
H15A	0.0367	0.5697	0.4215	0.047*
C16	−0.00662 (11)	0.72264 (16)	0.3475 (2)	0.0452 (5)
H16A	−0.0540	0.6983	0.2713	0.054*
C17	0.00987 (11)	0.83361 (16)	0.3721 (2)	0.0440 (5)
C18	0.07783 (11)	0.87337 (15)	0.4788 (2)	0.0439 (4)
H18A	0.0874	0.9510	0.4924	0.053*
C19	0.13208 (11)	0.79758 (14)	0.56618 (18)	0.0366 (4)
H19A	0.1801	0.8228	0.6407	0.044*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0310 (2)	0.0315 (2)	0.0284 (2)	−0.00616 (17)	0.00148 (16)	−0.00040 (17)
F1	0.0426 (6)	0.0621 (8)	0.0852 (9)	0.0135 (5)	0.0064 (6)	0.0321 (6)
O11	0.0376 (6)	0.0446 (7)	0.0257 (6)	−0.0085 (5)	0.0024 (5)	−0.0055 (5)
O12	0.0394 (6)	0.0390 (7)	0.0435 (7)	−0.0114 (5)	0.0015 (5)	0.0075 (6)
N1	0.0375 (7)	0.0345 (8)	0.0320 (8)	−0.0019 (6)	0.0089 (6)	0.0072 (6)
N2	0.0310 (7)	0.0302 (7)	0.0353 (8)	−0.0023 (6)	0.0001 (6)	−0.0086 (6)
C1	0.0323 (8)	0.0345 (9)	0.0270 (8)	0.0057 (7)	0.0085 (7)	−0.0026 (7)
C2	0.0334 (9)	0.0494 (11)	0.0352 (10)	−0.0026 (8)	0.0083 (8)	−0.0054 (8)
C3	0.0327 (9)	0.0608 (13)	0.0362 (10)	0.0064 (9)	0.0025 (8)	−0.0101 (9)
C4	0.0408 (10)	0.0514 (12)	0.0292 (9)	0.0172 (9)	−0.0005 (8)	0.0005 (8)
C5	0.0403 (9)	0.0351 (9)	0.0277 (9)	0.0089 (7)	0.0059 (7)	0.0025 (7)
C6	0.0296 (8)	0.0301 (9)	0.0237 (8)	0.0066 (7)	0.0076 (6)	−0.0019 (7)
C7	0.0313 (8)	0.0260 (8)	0.0213 (8)	0.0058 (6)	0.0068 (6)	0.0001 (6)
C8	0.0337 (8)	0.0290 (8)	0.0250 (8)	0.0039 (7)	0.0044 (6)	0.0030 (6)
C9	0.0296 (8)	0.0272 (9)	0.0264 (8)	0.0005 (6)	0.0006 (6)	−0.0037 (6)
C10	0.0420 (9)	0.0326 (9)	0.0262 (8)	0.0060 (8)	−0.0007 (7)	0.0030 (7)
C11	0.0411 (9)	0.0330 (9)	0.0288 (9)	0.0049 (7)	0.0025 (7)	0.0085 (7)
C12	0.0315 (8)	0.0288 (8)	0.0249 (8)	0.0052 (7)	0.0070 (6)	0.0000 (6)
C13	0.0530 (11)	0.0365 (10)	0.0424 (11)	−0.0068 (8)	0.0040 (9)	−0.0142 (8)
C14	0.0265 (8)	0.0338 (9)	0.0296 (8)	−0.0027 (7)	0.0079 (7)	−0.0009 (7)
C15	0.0331 (9)	0.0374 (10)	0.0433 (10)	−0.0041 (8)	0.0016 (8)	−0.0004 (8)
C16	0.0312 (9)	0.0528 (12)	0.0470 (11)	−0.0038 (8)	−0.0014 (8)	0.0048 (9)
C17	0.0301 (9)	0.0495 (12)	0.0541 (12)	0.0086 (8)	0.0129 (8)	0.0181 (9)
C18	0.0402 (10)	0.0322 (10)	0.0618 (12)	0.0023 (8)	0.0167 (9)	0.0035 (9)
C19	0.0325 (8)	0.0363 (10)	0.0407 (10)	−0.0032 (7)	0.0070 (7)	−0.0035 (8)

Geometric parameters (Å, º) top

S1—O11	1.4305 (11)	C8—H8A	0.990
S1—O12	1.4312 (11)	C8—H8B	0.990
S1—N2	1.6131 (13)	C9—C10	1.520 (2)
S1—C14	1.7660 (16)	C9—H9A	1.000
F1—C17	1.3572 (19)	C10—C11	1.524 (2)
N1—C1	1.3733 (19)	C10—H10A	0.990
N1—C12	1.3751 (19)	C10—H10B	0.990
N1—H1	0.880	C11—C12	1.495 (2)
N2—C13	1.4640 (19)	C11—H11A	0.990
N2—C9	1.4817 (19)	C11—H11B	0.990
C1—C2	1.396 (2)	C13—H13A	0.980
C1—C6	1.411 (2)	C13—H13B	0.980
C2—C3	1.376 (2)	C13—H13C	0.980
C2—H2A	0.950	C14—C19	1.384 (2)
C3—C4	1.392 (3)	C14—C15	1.388 (2)
C3—H3A	0.950	C15—C16	1.378 (2)
C4—C5	1.383 (2)	C15—H15A	0.950
C4—H4A	0.950	C16—C17	1.369 (3)
C5—C6	1.397 (2)	C16—H16A	0.950
C5—H5A	0.950	C17—C18	1.368 (2)
C6—C7	1.437 (2)	C18—C19	1.380 (2)
C7—C12	1.361 (2)	C18—H18A	0.950
C7—C8	1.498 (2)	C19—H19A	0.950
C8—C9	1.526 (2)

O11—S1—O12	119.71 (7)	N2—C9—H9A	107.1
O11—S1—N2	106.80 (6)	C10—C9—H9A	107.1
O12—S1—N2	106.93 (7)	C8—C9—H9A	107.1
O11—S1—C14	107.14 (7)	C9—C10—C11	110.79 (13)
O12—S1—C14	107.08 (7)	C9—C10—H10A	109.5
N2—S1—C14	108.84 (7)	C11—C10—H10A	109.5
C1—N1—C12	109.04 (13)	C9—C10—H10B	109.5
C1—N1—H1	125.5	C11—C10—H10B	109.5
C12—N1—H1	125.5	H10A—C10—H10B	108.1
C13—N2—C9	118.58 (13)	C12—C11—C10	109.94 (13)
C13—N2—S1	118.77 (11)	C12—C11—H11A	109.7
C9—N2—S1	119.01 (10)	C10—C11—H11A	109.7
N1—C1—C2	130.16 (15)	C12—C11—H11B	109.7
N1—C1—C6	107.44 (13)	C10—C11—H11B	109.7
C2—C1—C6	122.39 (14)	H11A—C11—H11B	108.2
C3—C2—C1	117.05 (16)	C7—C12—N1	109.95 (13)
C3—C2—H2A	121.5	C7—C12—C11	125.57 (14)
C1—C2—H2A	121.5	N1—C12—C11	124.45 (13)
C2—C3—C4	121.77 (16)	N2—C13—H13A	109.5
C2—C3—H3A	119.1	N2—C13—H13B	109.5
C4—C3—H3A	119.1	H13A—C13—H13B	109.5
C5—C4—C3	121.13 (16)	N2—C13—H13C	109.5
C5—C4—H4A	119.4	H13A—C13—H13C	109.5
C3—C4—H4A	119.4	H13B—C13—H13C	109.5
C4—C5—C6	118.89 (16)	C19—C14—C15	120.47 (15)
C4—C5—H5A	120.6	C19—C14—S1	120.04 (12)
C6—C5—H5A	120.6	C15—C14—S1	119.49 (12)
C5—C6—C1	118.77 (14)	C16—C15—C14	119.64 (16)
C5—C6—C7	134.35 (15)	C16—C15—H15A	120.2
C1—C6—C7	106.87 (13)	C14—C15—H15A	120.2
C12—C7—C6	106.70 (13)	C17—C16—C15	118.47 (16)
C12—C7—C8	122.71 (13)	C17—C16—H16A	120.8
C6—C7—C8	130.38 (13)	C15—C16—H16A	120.8
C7—C8—C9	108.04 (12)	F1—C17—C18	118.30 (17)
C7—C8—H8A	110.1	F1—C17—C16	118.42 (17)
C9—C8—H8A	110.1	C18—C17—C16	123.28 (17)
C7—C8—H8B	110.1	C17—C18—C19	118.16 (16)
C9—C8—H8B	110.1	C17—C18—H18A	120.9
H8A—C8—H8B	108.4	C19—C18—H18A	120.9
N2—C9—C10	113.79 (12)	C18—C19—C14	119.97 (16)
N2—C9—C8	110.22 (12)	C18—C19—H19A	120.0
C10—C9—C8	111.13 (12)	C14—C19—H19A	120.0

O11—S1—N2—C13	171.11 (11)	C7—C8—C9—N2	179.29 (12)
O12—S1—N2—C13	41.83 (14)	C7—C8—C9—C10	52.20 (16)
C14—S1—N2—C13	−73.52 (13)	N2—C9—C10—C11	168.46 (12)
O11—S1—N2—C9	−30.69 (13)	C8—C9—C10—C11	−66.42 (17)
O12—S1—N2—C9	−159.97 (11)	C9—C10—C11—C12	40.74 (18)
C14—S1—N2—C9	84.67 (12)	C6—C7—C12—N1	−0.90 (17)
C12—N1—C1—C2	179.04 (16)	C8—C7—C12—N1	174.28 (13)
C12—N1—C1—C6	0.25 (16)	C6—C7—C12—C11	−179.17 (14)
N1—C1—C2—C3	−177.84 (15)	C8—C7—C12—C11	−4.0 (2)
C6—C1—C2—C3	0.8 (2)	C1—N1—C12—C7	0.42 (17)
C1—C2—C3—C4	−0.1 (2)	C1—N1—C12—C11	178.71 (14)
C2—C3—C4—C5	−0.6 (3)	C10—C11—C12—C7	−7.3 (2)
C3—C4—C5—C6	0.5 (2)	C10—C11—C12—N1	174.63 (14)
C4—C5—C6—C1	0.2 (2)	O11—S1—C14—C19	16.81 (14)
C4—C5—C6—C7	178.64 (16)	O12—S1—C14—C19	146.41 (13)
N1—C1—C6—C5	178.01 (13)	N2—S1—C14—C19	−98.34 (14)
C2—C1—C6—C5	−0.9 (2)	O11—S1—C14—C15	−163.65 (12)
N1—C1—C6—C7	−0.79 (16)	O12—S1—C14—C15	−34.05 (14)
C2—C1—C6—C7	−179.70 (14)	N2—S1—C14—C15	81.21 (13)
C5—C6—C7—C12	−177.49 (16)	C19—C14—C15—C16	−0.1 (2)
C1—C6—C7—C12	1.04 (16)	S1—C14—C15—C16	−179.68 (13)
C5—C6—C7—C8	7.8 (3)	C14—C15—C16—C17	−0.6 (2)
C1—C6—C7—C8	−173.64 (14)	C15—C16—C17—F1	−179.37 (15)
C12—C7—C8—C9	−18.43 (19)	C15—C16—C17—C18	0.9 (3)
C6—C7—C8—C9	155.51 (15)	F1—C17—C18—C19	179.96 (14)
C13—N2—C9—C10	36.64 (19)	C16—C17—C18—C19	−0.3 (3)
S1—N2—C9—C10	−121.59 (13)	C17—C18—C19—C14	−0.5 (2)
C13—N2—C9—C8	−88.96 (16)	C15—C14—C19—C18	0.7 (2)
S1—N2—C9—C8	112.81 (12)	S1—C14—C19—C18	−179.72 (12)

Experimental details

Crystal data
Chemical formula	C₁₉H₁₉FN₂O₂S
M_r	358.42
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	180
a, b, c (Å)	15.2748 (7), 12.0319 (6), 9.4430 (4)
β (°)	102.445 (2)
V (Å³)	1694.70 (14)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.22
Crystal size (mm)	0.20 × 0.20 × 0.08

Data collection
Diffractometer	Bruker–Nonius X8 APEX-II CCD diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 2003)
T_min, T_max	0.870, 0.983
No. of measured, independent and observed [I > 2σ(I)] reflections	29053, 4157, 2816
R_int	0.039
(sin θ/λ)_max (Å⁻¹)	0.669

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.039, 0.100, 1.03
No. of reflections	4157
No. of parameters	227
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.28, −0.36

Computer programs: APEX2 (Bruker, 2004), SAINT (Bruker, 2003), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Acknowledgements

We are grateful to the Danish Natural Sciences Research Council and the Carlsberg Foundation for provision of the X-ray equipment.

References

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