Bis(benzothia­zol-2-ylmeth­yl)amine

Zhang, Y.; Zhao, B.; Zhang, S.; Qu, Y.; Xia, X.

doi:10.1107/S1600536809023435

organic compounds

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ISSN: 2056-9890

Volume 65| Part 7| July 2009| Page o1674

doi:10.1107/S1600536809023435

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Bis(benzothiazol-2-ylmethyl)amine

Yong Zhang,^a ^* Bi-lin Zhao,^a Shi-lei Zhang,^a Yuan Qu ^a and Xian-you Xia ^a

^aSchool of Chemical and Materials Engineering, Huangshi Institute of Technology, Huangshi 435003, People's Republic of China
^*Correspondence e-mail: zy0340907@yahoo.com.cn

(Received 5 June 2009; accepted 18 June 2009; online 24 June 2009)

In the title compound, C₁₆H₁₃N₃S₂, the dihedral angle between the two benzothiazole ring systems is 20.41 (2)°. In the crystal structure, intermolecular N—H⋯N hydrogen bonds link molecules into a chain along the b axis. The packing is further stabilized by C—H⋯π stacking interactions involving the two benzothiazole ring systems.

Related literature

For applications of benzothiazole devivatives, see: Pinheiro et al. (1990 ); Emad et al. (2009 ). For their use as ligands, see: Oughtred et al. (1982 ); Akther et al. (2008 ). For related structures, see: Laurence et al. (1980 .

Experimental

Crystal data

C₁₆H₁₃N₃S₂
M_r = 311.41
Monoclinic, P 2₁
a = 7.8478 (5) Å
b = 5.8042 (3) Å
c = 16.1548 (9) Å
β = 97.910 (1)°
V = 728.85 (7) Å³
Z = 2
Mo Kα radiation
μ = 0.36 mm⁻¹
T = 298 K
0.23 × 0.12 × 0.10 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2001 ) T_min = 0.889, T_max = 0.965
9009 measured reflections
3603 independent reflections
3473 reflections with I > 2σ(I)
R_int = 0.032

Refinement

R[F² > 2σ(F²)] = 0.029
wR(F²) = 0.079
S = 1.07
3603 reflections
193 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.19 e Å⁻³
Δρ_min = −0.22 e Å⁻³
Absolute structure: Flack (1983 ), 1623 Friedel pairs
Flack parameter: −0.07 (4)

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯N2ⁱ	0.821 (19)	2.489 (19)	3.3054 (18)	173.5 (17)
C1—H1⋯Cg1ⁱⁱ	0.97	2.78	3.737 (16)	168
C9—H9⋯Cg2ⁱⁱ	0.97	2.73	3.689 (17)	170
C14—H14⋯Cg3ⁱⁱⁱ	0.93	2.89	3.598 (2)	134
Symmetry codes: (i) $[-x+1, y+{\script{1\over 2}}, -z+2]$ ; (ii) $[-x+1, y-{\script{1\over 2}}, -z+2]$ ; (iii) $[-x, y+{\script{1\over 2}}, -z+1]$ . Cg1, Cg2, Cg3 are the centroids of the S1,C2,N2,C3,C8, C3–C8 and C11–C16 rings, respectively.

Data collection: SMART (Bruker, 2001); cell refinement: SAINT-Plus (Bruker, 2001; data reduction: SAINT-Plus 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: SHELXTL (Sheldrick, 2008).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809023435/pk2169sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809023435/pk2169Isup2.hkl

checkCIF report

Comment top

Benzothiazole devivatives have been used as photostablizers and metal chelating agents (Pinheiro et al., 1990; Emad et al., 2009). Many chelating heterocyclic ligands bearing benzothiazole group have been reported in recent years (Oughtred et al., 1982; Akther et al., 2008). The wide range of application of the benzothiazole chelators and their metal complexes aroused our interest to prepare a new series of metal complexes. With this mind, the title compound was prepared and we report the crystal stucture herein.

In the molecular structure (Fig. 1), the dihedral angle between the two benzothiazole ring systems is 20.41 (2)°. The C—N bond distances range from 1.2906 (18) to 1.4567 (18) Å, and the C—N(amino) bonds are longer than the C—N (benzothiazolyl) bonds. In the crystal structure (Fig. 2), intermolecular N—H···N hydrogen bond links molecules into a chain along the b axis. The packing is further stabilized by C—H···π stacking interactions involving two benzothiazole ring systems.

Related literature top

For general background, see: Emad et al. (2009); Pinheiro et al. (1990). For related structures, see: Akther et al. (2008); Laurence et al. (1980); Oughtred et al. (1982).

Experimental top

The title compound was synthesized according to a literature procedure (Laurence et al., 1980). Single crystals suitable for X-ray diffraction were obtained by slow evaporation of a dichloromethane solution at room temperature.

Computing details top

Data collection: SMART (Bruker, 2001); cell refinement: SAINT-Plus (Bruker, 2001; data reduction: SAINT-Plus (Bruker, 2001; 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: SHELXTL (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structure with displacement ellipsoids drawn at the 50% probability level.
	Fig. 2. Part of the crystal structure showing hydrogen bonds as dashed lines.

Bis(benzothiazol-2-ylmethyl)amine top

Crystal data top

C₁₆H₁₃N₃S₂	F(000) = 324
M_r = 311.41	D_x = 1.419 Mg m⁻³
Monoclinic, P2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2yb	Cell parameters from 6428 reflections
a = 7.8478 (5) Å	θ = 2.6–28.2°
b = 5.8042 (3) Å	µ = 0.36 mm⁻¹
c = 16.1548 (9) Å	T = 298 K
β = 97.910 (1)°	Block, colourless
V = 728.85 (7) Å³	0.23 × 0.12 × 0.10 mm
Z = 2

Data collection top

Bruker SMART APEX CCD area-detector diffractometer	3603 independent reflections
Radiation source: fine focus sealed Siemens Mo tube	3473 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.032
0.3° wide ω exposures scans	θ_max = 28.3°, θ_min = 2.6°
Absorption correction: multi-scan (SADABS; Sheldrick, 2001)	h = −10→10
T_min = 0.889, T_max = 0.965	k = −7→7
9009 measured reflections	l = −21→21

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)] = 0.029	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.079	w = 1/[σ²(F_o²) + (0.0549P)² + 0.0014P] where P = (F_o² + 2F_c²)/3
S = 1.07	(Δ/σ)_max = 0.002
3603 reflections	Δρ_max = 0.19 e Å⁻³
193 parameters	Δρ_min = −0.22 e Å⁻³
1 restraint	Absolute structure: Flack (1983), 1621 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: −0.07 (4)

Crystal data top

C₁₆H₁₃N₃S₂	V = 728.85 (7) Å³
M_r = 311.41	Z = 2
Monoclinic, P2₁	Mo Kα radiation
a = 7.8478 (5) Å	µ = 0.36 mm⁻¹
b = 5.8042 (3) Å	T = 298 K
c = 16.1548 (9) Å	0.23 × 0.12 × 0.10 mm
β = 97.910 (1)°

Data collection top

Bruker SMART APEX CCD area-detector diffractometer	3603 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 2001)	3473 reflections with I > 2σ(I)
T_min = 0.889, T_max = 0.965	R_int = 0.032
9009 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.029	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.079	Δρ_max = 0.19 e Å⁻³
S = 1.07	Δρ_min = −0.22 e Å⁻³
3603 reflections	Absolute structure: Flack (1983), 1621 Friedel pairs
193 parameters	Absolute structure parameter: −0.07 (4)
1 restraint

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
C1	0.32522 (18)	−0.2480 (3)	0.92805 (8)	0.0469 (3)
H1A	0.4335	−0.3306	0.9380	0.056*
H1B	0.2355	−0.3573	0.9078	0.056*
C2	0.28685 (17)	−0.1421 (3)	1.00759 (9)	0.0421 (3)
C3	0.27501 (17)	−0.0905 (3)	1.14199 (9)	0.0419 (3)
C4	0.30208 (19)	−0.1344 (3)	1.22742 (9)	0.0508 (3)
H4	0.3569	−0.2685	1.2483	0.061*
C5	0.2453 (2)	0.0270 (3)	1.28049 (10)	0.0563 (4)
H5	0.2626	0.0001	1.3378	0.068*
C6	0.1634 (2)	0.2274 (4)	1.25053 (10)	0.0552 (4)
H6	0.1279	0.3328	1.2880	0.066*
C7	0.13337 (18)	0.2734 (3)	1.16584 (9)	0.0512 (3)
H7	0.0775	0.4074	1.1456	0.061*
C8	0.18981 (17)	0.1116 (3)	1.11172 (8)	0.0430 (3)
C9	0.3518 (2)	−0.1629 (3)	0.78314 (9)	0.0520 (4)
H9A	0.2734	−0.2916	0.7712	0.062*
H9B	0.4680	−0.2194	0.7827	0.062*
C10	0.31251 (18)	0.0167 (3)	0.71708 (9)	0.0440 (3)
C11	0.30569 (18)	0.1982 (3)	0.59715 (9)	0.0463 (3)
C12	0.3417 (2)	0.2449 (4)	0.51678 (10)	0.0589 (4)
H12	0.4135	0.1486	0.4912	0.071*
C13	0.2688 (2)	0.4370 (4)	0.47583 (10)	0.0628 (5)
H13	0.2930	0.4705	0.4224	0.075*
C14	0.1602 (2)	0.5812 (4)	0.51276 (11)	0.0617 (4)
H14	0.1131	0.7100	0.4840	0.074*
C15	0.1213 (2)	0.5352 (3)	0.59197 (11)	0.0571 (4)
H15	0.0482	0.6313	0.6168	0.069*
C16	0.19401 (18)	0.3417 (3)	0.63367 (9)	0.0449 (3)
N1	0.33530 (16)	−0.0701 (2)	0.86544 (8)	0.0462 (3)
H1	0.413 (2)	0.023 (3)	0.8796 (11)	0.055*
N2	0.32946 (14)	−0.2309 (2)	1.08061 (7)	0.0448 (3)
N3	0.37321 (16)	0.0144 (3)	0.64678 (8)	0.0499 (3)
S1	0.17864 (5)	0.12218 (6)	1.00381 (2)	0.04752 (10)
S2	0.17133 (5)	0.23922 (7)	0.73265 (2)	0.05010 (11)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0526 (7)	0.0424 (7)	0.0455 (7)	0.0054 (7)	0.0062 (6)	0.0017 (6)
C2	0.0395 (6)	0.0388 (7)	0.0475 (7)	0.0010 (5)	0.0043 (5)	0.0032 (6)
C3	0.0399 (6)	0.0417 (7)	0.0443 (7)	−0.0007 (5)	0.0062 (5)	0.0049 (5)
C4	0.0519 (8)	0.0532 (8)	0.0471 (8)	0.0010 (7)	0.0059 (6)	0.0091 (7)
C5	0.0587 (9)	0.0677 (10)	0.0437 (8)	−0.0003 (8)	0.0109 (7)	0.0042 (7)
C6	0.0572 (8)	0.0576 (9)	0.0528 (8)	0.0004 (8)	0.0145 (6)	−0.0076 (8)
C7	0.0522 (8)	0.0476 (8)	0.0536 (8)	0.0050 (7)	0.0065 (6)	0.0001 (7)
C8	0.0416 (6)	0.0446 (7)	0.0425 (6)	−0.0012 (6)	0.0044 (5)	0.0024 (6)
C9	0.0669 (9)	0.0443 (8)	0.0453 (8)	0.0058 (7)	0.0093 (7)	−0.0039 (6)
C10	0.0469 (6)	0.0413 (7)	0.0435 (7)	0.0005 (6)	0.0046 (5)	−0.0077 (6)
C11	0.0440 (7)	0.0546 (9)	0.0392 (6)	−0.0016 (6)	0.0022 (5)	−0.0045 (6)
C12	0.0568 (8)	0.0778 (12)	0.0426 (7)	0.0046 (9)	0.0082 (6)	−0.0028 (9)
C13	0.0641 (9)	0.0788 (13)	0.0439 (8)	−0.0109 (9)	0.0011 (7)	0.0083 (8)
C14	0.0631 (9)	0.0596 (11)	0.0592 (9)	−0.0012 (8)	−0.0036 (7)	0.0124 (8)
C15	0.0592 (8)	0.0528 (9)	0.0589 (9)	0.0037 (8)	0.0059 (7)	0.0034 (8)
C16	0.0432 (7)	0.0445 (7)	0.0469 (7)	−0.0045 (6)	0.0055 (5)	−0.0024 (6)
N1	0.0540 (7)	0.0441 (7)	0.0405 (6)	−0.0066 (6)	0.0063 (5)	−0.0029 (5)
N2	0.0470 (6)	0.0423 (6)	0.0454 (6)	0.0026 (5)	0.0079 (5)	0.0056 (5)
N3	0.0542 (6)	0.0545 (7)	0.0411 (6)	0.0064 (6)	0.0066 (5)	−0.0048 (6)
S1	0.0553 (2)	0.04359 (19)	0.04214 (17)	0.00959 (16)	0.00134 (13)	0.00366 (15)
S2	0.0592 (2)	0.04371 (19)	0.05053 (19)	0.00410 (16)	0.01872 (15)	−0.00142 (15)

Geometric parameters (Å, º) top

C1—N1	1.4554 (19)	C9—C10	1.493 (2)
C1—C2	1.4922 (19)	C9—H9A	0.9700
C1—H1A	0.9700	C9—H9B	0.9700
C1—H1B	0.9700	C10—N3	1.2906 (18)
C2—N2	1.2884 (18)	C10—S2	1.7424 (15)
C2—S1	1.7503 (15)	C11—C12	1.393 (2)
C3—C4	1.391 (2)	C11—N3	1.394 (2)
C3—N2	1.3951 (18)	C11—C16	1.397 (2)
C3—C8	1.404 (2)	C12—C13	1.380 (3)
C4—C5	1.384 (2)	C12—H12	0.9300
C4—H4	0.9300	C13—C14	1.387 (3)
C5—C6	1.383 (3)	C13—H13	0.9300
C5—H5	0.9300	C14—C15	1.382 (2)
C6—C7	1.382 (2)	C14—H14	0.9300
C6—H6	0.9300	C15—C16	1.391 (2)
C7—C8	1.396 (2)	C15—H15	0.9300
C7—H7	0.9300	C16—S2	1.7382 (15)
C8—S1	1.7344 (13)	N1—H1	0.821 (19)
C9—N1	1.4567 (18)

N1—C1—C2	110.05 (13)	C10—C9—H9B	109.4
N1—C1—H1A	109.7	H9A—C9—H9B	108.0
C2—C1—H1A	109.7	N3—C10—C9	123.85 (14)
N1—C1—H1B	109.7	N3—C10—S2	116.97 (13)
C2—C1—H1B	109.7	C9—C10—S2	119.14 (11)
H1A—C1—H1B	108.2	C12—C11—N3	125.12 (15)
N2—C2—C1	124.47 (14)	C12—C11—C16	119.78 (16)
N2—C2—S1	116.49 (12)	N3—C11—C16	115.10 (12)
C1—C2—S1	119.04 (11)	C13—C12—C11	118.72 (17)
C4—C3—N2	125.36 (14)	C13—C12—H12	120.6
C4—C3—C8	119.93 (14)	C11—C12—H12	120.6
N2—C3—C8	114.70 (12)	C12—C13—C14	121.34 (16)
C5—C4—C3	118.20 (15)	C12—C13—H13	119.3
C5—C4—H4	120.9	C14—C13—H13	119.3
C3—C4—H4	120.9	C15—C14—C13	120.60 (17)
C6—C5—C4	121.73 (15)	C15—C14—H14	119.7
C6—C5—H5	119.1	C13—C14—H14	119.7
C4—C5—H5	119.1	C14—C15—C16	118.44 (16)
C7—C6—C5	121.09 (17)	C14—C15—H15	120.8
C7—C6—H6	119.5	C16—C15—H15	120.8
C5—C6—H6	119.5	C15—C16—C11	121.09 (14)
C6—C7—C8	117.68 (16)	C15—C16—S2	129.40 (13)
C6—C7—H7	121.2	C11—C16—S2	109.50 (11)
C8—C7—H7	121.2	C1—N1—C9	113.07 (13)
C7—C8—C3	121.37 (13)	C1—N1—H1	112.4 (13)
C7—C8—S1	128.98 (12)	C9—N1—H1	110.0 (12)
C3—C8—S1	109.60 (11)	C2—N2—C3	110.55 (13)
N1—C9—C10	111.02 (13)	C10—N3—C11	109.95 (13)
N1—C9—H9A	109.4	C8—S1—C2	88.66 (7)
C10—C9—H9A	109.4	C16—S2—C10	88.47 (7)
N1—C9—H9B	109.4

N1—C1—C2—N2	−153.63 (14)	C12—C11—C16—C15	−1.8 (2)
N1—C1—C2—S1	25.69 (16)	N3—C11—C16—C15	178.18 (14)
N2—C3—C4—C5	177.62 (14)	C12—C11—C16—S2	179.13 (13)
C8—C3—C4—C5	−0.9 (2)	N3—C11—C16—S2	−0.91 (16)
C3—C4—C5—C6	0.1 (2)	C2—C1—N1—C9	−173.01 (13)
C4—C5—C6—C7	0.6 (3)	C10—C9—N1—C1	164.09 (13)
C5—C6—C7—C8	−0.5 (2)	C1—C2—N2—C3	−179.90 (13)
C6—C7—C8—C3	−0.4 (2)	S1—C2—N2—C3	0.76 (16)
C6—C7—C8—S1	−177.64 (12)	C4—C3—N2—C2	−179.17 (14)
C4—C3—C8—C7	1.1 (2)	C8—C3—N2—C2	−0.58 (18)
N2—C3—C8—C7	−177.61 (13)	C9—C10—N3—C11	176.92 (14)
C4—C3—C8—S1	178.83 (11)	S2—C10—N3—C11	−0.93 (17)
N2—C3—C8—S1	0.15 (15)	C12—C11—N3—C10	−178.86 (15)
N1—C9—C10—N3	154.02 (15)	C16—C11—N3—C10	1.18 (18)
N1—C9—C10—S2	−28.18 (18)	C7—C8—S1—C2	177.75 (14)
N3—C11—C12—C13	−178.31 (16)	C3—C8—S1—C2	0.21 (10)
C16—C11—C12—C13	1.7 (2)	N2—C2—S1—C8	−0.59 (11)
C11—C12—C13—C14	−0.6 (3)	C1—C2—S1—C8	−179.96 (12)
C12—C13—C14—C15	−0.3 (3)	C15—C16—S2—C10	−178.68 (16)
C13—C14—C15—C16	0.2 (3)	C11—C16—S2—C10	0.31 (11)
C14—C15—C16—C11	0.8 (2)	N3—C10—S2—C16	0.37 (13)
C14—C15—C16—S2	179.72 (13)	C9—C10—S2—C16	−177.58 (13)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···N2ⁱ	0.821 (19)	2.489 (19)	3.3054 (18)	173.5 (17)
C1—H1···Cg1ⁱⁱ	0.97	2.78	3.737 (16)	168
C9—H9···Cg2ⁱⁱ	0.97	2.73	3.689 (17)	170
C14—H14···Cg3ⁱⁱⁱ	0.93	2.89	3.598 (2)	134

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

Experimental details

Crystal data
Chemical formula	C₁₆H₁₃N₃S₂
M_r	311.41
Crystal system, space group	Monoclinic, P2₁
Temperature (K)	298
a, b, c (Å)	7.8478 (5), 5.8042 (3), 16.1548 (9)
β (°)	97.910 (1)
V (Å³)	728.85 (7)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.36
Crystal size (mm)	0.23 × 0.12 × 0.10

Data collection
Diffractometer	Bruker SMART APEX CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 2001)
T_min, T_max	0.889, 0.965
No. of measured, independent and observed [I > 2σ(I)] reflections	9009, 3603, 3473
R_int	0.032
(sin θ/λ)_max (Å⁻¹)	0.666

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.029, 0.079, 1.07
No. of reflections	3603
No. of parameters	193
No. of restraints	1
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.19, −0.22
Absolute structure	Flack (1983), 1621 Friedel pairs
Absolute structure parameter	−0.07 (4)

Computer programs: SMART (Bruker, 2001), SAINT-Plus (Bruker, 2001, SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), PLATON (Spek, 2009), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···N2ⁱ	0.821 (19)	2.489 (19)	3.3054 (18)	173.5 (17)
C1—H1···Cg1ⁱⁱ	0.97	2.78	3.737 (16)	168
C9—H9···Cg2ⁱⁱ	0.97	2.73	3.689 (17)	170
C14—H14···Cg3ⁱⁱⁱ	0.93	2.89	3.598 (2)	134

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

References

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Volume 65| Part 7| July 2009| Page o1674

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