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(Z) 4 Benzyl­­idene 1 (4 chloro­phen­yl) 2 propyl­amino 1H imidazol 5(4H) one

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organic papers

o2090

Sunet al. C

19H18ClN3O doi:10.1107/S160053680601467X Acta Cryst.(2006). E62, o2090–o2091

Acta Crystallographica Section E Structure Reports

Online

ISSN 1600-5368

(

Z

)-4-Benzylidene-1-(4-chlorophenyl)-2-propyl-amino-1

H

-imidazol-5(4

H

)-one

Shao-Fa Sun,aRong-Ming Maa and

Seik Weng Ngb*

aDepartment of Chemistry and Life Science,

Xianning College, Xianning 437100, People’s Republic of China, andbDepartment of

Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia

Correspondence e-mail: seikweng@um.edu.my

Key indicators

Single-crystal X-ray study T= 292 K

Mean(C–C) = 0.003 A˚ Disorder in main residue Rfactor = 0.052 wRfactor = 0.139

Data-to-parameter ratio = 16.5

For details of how these key indicators were automatically derived from the article, see http://journals.iucr.org/e.

Received 21 April 2006 Accepted 22 April 2006

#2006 International Union of Crystallography

All rights reserved

Adjacent molecules of the title compound, C19H18ClN3O, are

linked by an N O hydrogen bond [2.926 (2) A˚ ] into a zigzag chain.

Comment

Several PhCH C(CO2Et)N C NR (R = Ph, 4-ClC6H4)

compounds that were synthesized from an aza-Wittig reaction of PhCH C(CO2Et)N PPh3withRNCO have been reacted

with primary amines to form 1-aryl-2-alkylamino-4-benzyl-ideneimidazolin-5-ones (Dinget al., 2001). Among these is the title compound (I) (Fig. 1), whose amino group is hydrogen-bonded with the carbonyl group of an adjacent molecule (Table 1), forming a zigzag chain running along thecaxis. The compound features an imidazolinone unit with an exocyclic C C double bond.

[image:1.610.231.433.570.717.2]

There are few related compounds whose structures have been determined. The examples appear to be limited to (4Z )- 4-(4-methoxybenzylidene)-1,2-diphenyl-1,4-dihydro-5-imida-zolin-5-one (Bhattacharjya et al., 2004), 1-[2-(dimethyl-amino)ethyl]-2-methyl-4-benzylidene-2-imidazolin-5-one (Oshimi et al., 2002) and (Z )-1-[2-(dimethylamino)ethyl]-2-methyl-4-benzylidene-2-imidazolin-5-one (Kawasaki et al., 2004).

Figure 1

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Experimental

The compound was synthesized according to a reported procedure (Dinget al., 2001) and crystals were grown from a dichloromethane/ diethyl ether solution (1:1v/v).

Crystal data

C19H18ClN3O

Mr= 339.81 Monoclinic,P21=c a= 10.9150 (7) A˚ b= 12.9335 (8) A˚ c= 12.8701 (8) A˚

= 103.331 (1) V= 1767.9 (2) A˚3

Z= 4

Dx= 1.277 Mg m 3

MoKradiation

= 0.23 mm1

T= 292 (2) K Block, yellow 0.20.20.2 mm

Data collection

Bruker SMART APEX area-detector diffractometer

’and!scans

Absorption correction: none 16744 measured reflections

4038 independent reflections 2612 reflections withI> 2(I) Rint= 0.050

max= 27.5

Refinement

Refinement onF2

R[F2> 2(F2)] = 0.052

wR(F2) = 0.139 S= 0.97 4038 reflections 245 parameters

H-atom parameters constrained w= 1/[2(F

o2) + (0.0731P)2]

whereP= (Fo2+ 2Fc2)/3

(/)max= 0.001

max= 0.18 e A˚ 3

min=0.23 e A˚ 3

Table 1

Hydrogen-bond geometry (A˚ ,).

D—H A D—H H A D A D—H A

N3—H3n O1i

0.86 2.15 2.926 (2) 150

N3—H3n0 O1i

0.86 2.36 2.926 (2) 124

Symmetry code: (i)x;yþ1 2;z

1 2.

The propyl chain is disordered over two positions; the occupancy factors refined to 0.612 (6):0.388 (2). The pairs of 1,2-related and 1,3-related distances were restrained to be equal within 0.01 A˚ . H atoms were positioned geometrically and were included in the refinement in the riding-model approximation [aryl C—H = 0.93 A˚ andUiso(H) =

1.2Ueq(C); methylene C—H = 0.97 A˚ and Uiso(H) = 1.2Ueq(C);

methyl C—H = 0.96 A˚ andUiso(H) = 1.5Ueq(C)]. Because of disorder

of the propyl group, the H atom bonded to atom N3 is disordered over two sites (H3nand H3n0), which were refined in riding mode,

with N—H = 0.86 A˚ andUiso(H) = 1.2Ueq(N).

Data collection:SMART(Bruker, 2003); cell refinement:SAINT

(Bruker, 2003); data reduction:SAINT; program(s) used to solve structure:SHELXS97(Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics:

SHELXTL (Bruker, 1998); software used to prepare material for publication:SHELXL97.

The authors thank Xianning College and the University of Malaya for supporting this work.

References

Bhattacharjya, G., Savitha, G. & Ramanathan, G. (2004).CrystEngComm,6, 233–235.

Bruker (1998).SHELXTL. Version 5. Bruker AXS Inc., Madison, Wisconsin, USA. (Could also be under Sheldrick, 1997).

Bruker (2003).SAINT (Version 6.45A) andSMART(Version 6.45A). Bruker AXS Inc., Madison, Wisconsin, USA.

Ding, M.-W., Xu, Z.-F., Liu, Z.-J. & Wu, T.-J. (2001).Synth. Commun.31, 1053– 1057.

Kawasaki, A., Maekawa, K., Kubo, K., Igarashi, T. & Sakurai, T. (2004). Tetrahedron,60, 9517–9524.

Oshimi, K., Kubo, K., Kawasaki, A., Maekawa, K., Igarashi, T. & Sakurai, T. (2002).Tetrahedron Lett.43, 3291–3294.

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supporting information

sup-1 Acta Cryst. (2006). E62, o2090–o2091

supporting information

Acta Cryst. (2006). E62, o2090–o2091 [https://doi.org/10.1107/S160053680601467X]

(

Z

)-4-Benzylidene-1-(4-chlorophenyl)-2-propylamino-1

H

-imidazol-5(4

H

)-one

Shao-Fa Sun, Rong-Ming Ma and Seik Weng Ng

(Z)-4-Benzylidene-1-(4-chlorophenyl)-2-propylamino-1H-imidazol-5(4H)-one

Crystal data

C19H18ClN3O Mr = 339.81

Monoclinic, P21/c

Hall symbol: -P 2ybc

a = 10.9150 (7) Å

b = 12.9335 (8) Å

c = 12.8701 (8) Å

β = 103.331 (1)°

V = 1767.9 (2) Å3 Z = 4

F(000) = 712

Dx = 1.277 Mg m−3

Mo radiation, λ = 0.71073 Å Cell parameters from 3657 reflections

θ = 2.3–22.4°

µ = 0.23 mm−1 T = 292 K Block, yellow 0.2 × 0.2 × 0.2 mm

Data collection

Bruker SMART APEX area-detector diffractometer

Radiation source: fine-focus sealed tube Graphite monochromator

φ and ω scans

16744 measured reflections 4038 independent reflections

2612 reflections with I > 2σ(I)

Rint = 0.050

θmax = 27.5°, θmin = 1.9° h = −13→14

k = −16→16

l = −16→16

Refinement

Refinement on F2

Least-squares matrix: full

R[F2 > 2σ(F2)] = 0.052 wR(F2) = 0.139 S = 0.97 4038 reflections 245 parameters 6 restraints

Primary atom site location: structure-invariant direct methods

Secondary atom site location: difference Fourier map

Hydrogen site location: inferred from neighbouring sites

H-atom parameters constrained

w = 1/[σ2(F

o2) + (0.0731P)2]

where P = (Fo2 + 2Fc2)/3

(Δ/σ)max = 0.001

Δρmax = 0.18 e Å−3

Δρmin = −0.23 e Å−3

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

x y z Uiso*/Ueq Occ. (<1)

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C1 0.31669 (17) 0.29834 (12) 0.71014 (12) 0.0501 (4) C2 0.42712 (18) 0.31034 (14) 0.67649 (14) 0.0627 (5) C3 0.4628 (2) 0.40693 (15) 0.64944 (16) 0.0707 (6) C4 0.3883 (2) 0.49045 (14) 0.65821 (15) 0.0670 (5) C5 0.2800 (2) 0.47964 (13) 0.69330 (15) 0.0672 (5) C6 0.24204 (19) 0.38243 (12) 0.71860 (14) 0.0587 (5) C7 0.24914 (16) 0.17200 (13) 0.83356 (13) 0.0515 (4) C8 0.21035 (16) 0.06162 (12) 0.81865 (12) 0.0490 (4) C9 0.25776 (17) 0.10995 (11) 0.67258 (13) 0.0504 (4) N3 0.27496 (18) 0.11197 (10) 0.57423 (11) 0.0679 (6)

C10 0.2742 (5) 0.0157 (3) 0.5131 (3) 0.0617 (13) 0.612 (3) C11 0.3783 (6) −0.0595 (4) 0.5588 (4) 0.0669 (14) 0.612 (3) C12 0.3847 (4) −0.1467 (2) 0.4812 (3) 0.0784 (11) 0.612 (3) C10′ 0.2100 (7) 0.0319 (6) 0.4949 (5) 0.073 (2) 0.388 (3) C11′ 0.3107 (6) −0.0366 (4) 0.4650 (5) 0.085 (2) 0.388 (3) C12′ 0.3775 (12) −0.1016 (7) 0.5578 (8) 0.101 (4) 0.388 (3) C13 0.16922 (17) 0.00765 (13) 0.89299 (13) 0.0553 (5)

C14 0.12379 (17) −0.09906 (13) 0.88653 (14) 0.0549 (5) C15 0.12365 (19) −0.16436 (14) 0.80050 (15) 0.0653 (5) C16 0.0783 (2) −0.26386 (15) 0.79929 (18) 0.0746 (6) C17 0.0332 (2) −0.30097 (17) 0.8838 (2) 0.0783 (6) C18 0.0319 (2) −0.23816 (17) 0.96882 (18) 0.0803 (6) C19 0.07598 (19) −0.13815 (16) 0.97019 (15) 0.0701 (6)

H2 0.4774 0.2532 0.6721 0.075*

H3 0.5363 0.4155 0.6256 0.085*

H5 0.2318 0.5374 0.7002 0.081*

H6 0.1674 0.3741 0.7409 0.070*

H3n 0.2867 0.1702 0.5457 0.081* 0.612 (3)

H10a 0.2800 0.0334 0.4411 0.074* 0.612 (3)

H10b 0.1941 −0.0187 0.5081 0.074* 0.612 (3)

H11a 0.3641 −0.0882 0.6247 0.080* 0.612 (3)

H11b 0.4581 −0.0231 0.5755 0.080* 0.612 (3)

H12a 0.4507 −0.1938 0.5132 0.118* 0.612 (3)

H12b 0.4019 −0.1187 0.4170 0.118* 0.612 (3)

H12c 0.3058 −0.1828 0.4645 0.118* 0.612 (3)

H3n′ 0.3224 0.1582 0.5557 0.081* 0.388 (3)

H10c 0.1606 0.0655 0.4317 0.087* 0.388 (3)

H10d 0.1540 −0.0098 0.5262 0.087* 0.388 (3)

H11c 0.2716 −0.0815 0.4063 0.102* 0.388 (3)

H11d 0.3716 0.0065 0.4412 0.102* 0.388 (3)

H12d 0.4458 −0.1379 0.5388 0.151* 0.388 (3)

H12e 0.3195 −0.1506 0.5757 0.151* 0.388 (3)

H12f 0.4097 −0.0579 0.6182 0.151* 0.388 (3)

H13 0.1697 0.0424 0.9564 0.066*

H15 0.1545 −0.1406 0.7433 0.078*

H16 0.0780 −0.3064 0.7410 0.089*

H17 0.0039 −0.3685 0.8829 0.094*

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supporting information

sup-3 Acta Cryst. (2006). E62, o2090–o2091

H19 0.0738 −0.0958 1.0282 0.084*

Atomic displacement parameters (Å2)

U11 U22 U33 U12 U13 U23

Cl1 0.1282 (6) 0.0640 (4) 0.1156 (5) −0.0377 (3) −0.0014 (4) 0.0183 (3) O1 0.1073 (12) 0.0613 (8) 0.0493 (7) −0.0058 (7) 0.0240 (7) −0.0138 (6) N1 0.0666 (10) 0.0408 (7) 0.0428 (7) −0.0013 (6) 0.0136 (7) −0.0012 (6) N2 0.0750 (10) 0.0430 (7) 0.0435 (8) 0.0001 (7) 0.0199 (7) 0.0022 (6) C1 0.0640 (12) 0.0431 (9) 0.0408 (8) −0.0034 (8) 0.0069 (8) −0.0014 (7) C2 0.0693 (13) 0.0545 (11) 0.0653 (12) −0.0015 (9) 0.0173 (10) −0.0002 (9) C3 0.0727 (14) 0.0690 (13) 0.0701 (13) −0.0183 (11) 0.0159 (11) 0.0025 (10) C4 0.0834 (15) 0.0510 (11) 0.0574 (11) −0.0184 (10) −0.0027 (10) 0.0030 (8) C5 0.0864 (15) 0.0457 (10) 0.0625 (11) 0.0035 (10) 0.0029 (11) −0.0008 (8) C6 0.0690 (13) 0.0492 (10) 0.0562 (11) 0.0042 (8) 0.0113 (9) −0.0003 (8) C7 0.0626 (12) 0.0509 (9) 0.0414 (9) 0.0038 (8) 0.0128 (8) −0.0009 (7) C8 0.0587 (11) 0.0477 (9) 0.0408 (8) 0.0047 (8) 0.0122 (8) 0.0017 (7) C9 0.0678 (12) 0.0412 (9) 0.0437 (9) 0.0035 (8) 0.0157 (8) 0.0010 (7) N3 0.1202 (16) 0.0446 (8) 0.0461 (9) −0.0110 (8) 0.0340 (9) −0.0010 (6) C10 0.096 (4) 0.046 (2) 0.050 (2) 0.007 (2) 0.031 (2) −0.0026 (17) C11 0.082 (3) 0.059 (3) 0.066 (3) 0.004 (2) 0.031 (2) −0.008 (2) C12 0.091 (3) 0.0538 (19) 0.097 (3) 0.0013 (17) 0.036 (2) −0.0169 (19) C10′ 0.118 (7) 0.050 (4) 0.057 (4) −0.005 (4) 0.034 (4) −0.007 (3) C11′ 0.122 (6) 0.075 (4) 0.068 (4) −0.022 (4) 0.042 (4) −0.016 (3) C12′ 0.131 (8) 0.073 (7) 0.097 (7) 0.014 (6) 0.022 (5) −0.001 (6) C13 0.0656 (12) 0.0595 (10) 0.0425 (9) 0.0026 (9) 0.0157 (8) 0.0009 (8) C14 0.0546 (11) 0.0591 (11) 0.0497 (10) 0.0013 (8) 0.0096 (8) 0.0101 (8) C15 0.0798 (14) 0.0562 (11) 0.0638 (12) 0.0016 (10) 0.0246 (10) 0.0074 (9) C16 0.0832 (16) 0.0569 (12) 0.0818 (14) 0.0013 (10) 0.0154 (12) 0.0035 (10) C17 0.0647 (14) 0.0647 (13) 0.0973 (16) −0.0073 (10) 0.0019 (12) 0.0229 (12) C18 0.0788 (16) 0.0881 (16) 0.0725 (14) −0.0181 (12) 0.0141 (12) 0.0260 (12) C19 0.0714 (14) 0.0843 (14) 0.0549 (11) −0.0126 (11) 0.0152 (10) 0.0106 (10)

Geometric parameters (Å, º)

Cl1—C4 1.735 (2) C18—C19 1.379 (3)

O1—C7 1.213 (2) C2—H2 0.93

N1—C7 1.386 (2) C3—H3 0.93

N1—C9 1.402 (2) C5—H5 0.93

N1—C1 1.431 (2) C6—H6 0.93

N2—C9 1.306 (2) N3—H3n 0.86

N2—C8 1.388 (2) C10—H10a 0.97

C1—C6 1.378 (2) C10—H10b 0.97

C1—C2 1.380 (2) C11—H11a 0.97

C2—C3 1.377 (2) C11—H11b 0.97

C3—C4 1.372 (3) C12—H12a 0.96

C4—C5 1.366 (3) C12—H12b 0.96

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C7—C8 1.489 (2) C10′—H10c 0.97

C8—C13 1.342 (2) C10′—H10d 0.97

C9—N3 1.322 (2) C11′—H11c 0.97

N3—C10 1.472 (4) C11′—H11d 0.97

C10—C11 1.508 (6) C12′—H12d 0.96

C11—C12 1.519 (5) C12′—H12e 0.96

C10′—C11′ 1.528 (7) C12′—H12f 0.96

C11′—C12′ 1.504 (8) C13—H13 0.93

C13—C14 1.462 (2) C15—H15 0.93

C14—C15 1.392 (3) C16—H16 0.93

C14—C19 1.395 (2) C17—H17 0.93

C15—C16 1.378 (2) C18—H18 0.93

C16—C17 1.379 (3) C19—H19 0.93

C17—C18 1.366 (3)

C7—N1—C9 107.2 (1) C9—N3—H3n 119.6

C7—N1—C1 125.6 (1) C10—N3—H3n 119.6

C9—N1—C1 127.2 (1) N3—C10—H10a 108.5

C9—N2—C8 106.1 (1) C11—C10—H10a 108.5

C6—C1—C2 120.7 (2) N3—C10—H10b 108.5

C6—C1—N1 118.7 (2) C11—C10—H10b 108.5

C2—C1—N1 120.6 (2) H10a—C10—H10b 107.5

C3—C2—C1 120.0 (2) C10—C11—H11a 109.3

C4—C3—C2 119.1 (2) C12—C11—H11a 109.3

C5—C4—C3 121.4 (2) C10—C11—H11b 109.3

C5—C4—Cl1 118.9 (2) C12—C11—H11b 109.3

C3—C4—Cl1 119.7 (2) H11a—C11—H11b 108.0

C4—C5—C6 119.9 (2) C11—C12—H12a 109.5

C1—C6—C5 118.9 (2) C11—C12—H12b 109.5

O1—C7—N1 125.5 (2) H12a—C12—H12b 109.5

O1—C7—C8 130.8 (2) C11—C12—H12c 109.5

N1—C7—C8 103.7 (1) H12a—C12—H12c 109.5

C13—C8—N2 128.3 (2) H12b—C12—H12c 109.5

C13—C8—C7 122.6 (1) C11′—C10′—H10c 110.0

N2—C8—C7 109.1 (1) C11′—C10′—H10d 110.0

N2—C9—N3 125.0 (2) H10c—C10′—H10d 108.4

N2—C9—N1 113.9 (1) C12′—C11′—H11c 109.3

N3—C9—N1 121.1 (1) C10′—C11′—H11c 109.3

C9—N3—C10 120.7 (2) C12′—C11′—H11d 109.3

N3—C10—C11 115.2 (4) C10′—C11′—H11d 109.3

C10—C11—C12 111.6 (4) H11c—C11′—H11d 108.0

C12′—C11′—C10′ 111.6 (6) C11′—C12′—H12d 109.5

C8—C13—C14 127.9 (2) C11′—C12′—H12e 109.5

C15—C14—C19 117.5 (2) H12d—C12′—H12e 109.5

C15—C14—C13 123.8 (2) C11′—C12′—H12f 109.5

C19—C14—C13 118.7 (2) H12d—C12′—H12f 109.5

C16—C15—C14 120.7 (2) H12e—C12′—H12f 109.5

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supporting information

sup-5 Acta Cryst. (2006). E62, o2090–o2091

C18—C17—C16 119.8 (2) C14—C13—H13 116.0

C17—C18—C19 120.0 (2) C16—C15—H15 119.7

C18—C19—C14 121.4 (2) C14—C15—H15 119.7

C3—C2—H2 120.0 C15—C16—H16 119.7

C1—C2—H2 120.0 C17—C16—H16 119.7

C4—C3—H3 120.5 C18—C17—H17 120.1

C2—C3—H3 120.5 C16—C17—H17 120.1

C4—C5—H5 120.0 C17—C18—H18 120.0

C6—C5—H5 120.0 C19—C18—H18 120.0

C1—C6—H6 120.6 C18—C19—H19 119.3

C5—C6—H6 120.6 C14—C19—H19 119.3

C7—N1—C1—C6 −54.4 (2) N1—C7—C8—N2 1.1 (2)

C9—N1—C1—C6 123.5 (2) C8—N2—C9—N3 −177.9 (2)

C7—N1—C1—C2 125.3 (2) C8—N2—C9—N1 1.3 (2)

C9—N1—C1—C2 −56.8 (3) C7—N1—C9—N2 −0.7 (2)

C6—C1—C2—C3 −1.0 (3) C1—N1—C9—N2 −178.9 (2)

N1—C1—C2—C3 179.4 (2) C7—N1—C9—N3 178.6 (2)

C1—C2—C3—C4 1.1 (3) C1—N1—C9—N3 0.4 (3)

C2—C3—C4—C5 0.1 (3) N2—C9—N3—C10 −11.0 (4)

C2—C3—C4—Cl1 −179.3 (2) N1—C9—N3—C10 169.8 (3)

C3—C4—C5—C6 −1.5 (3) C9—N3—C10—C11 −63.8 (5)

Cl1—C4—C5—C6 178.0 (1) N3—C10—C11—C12 −169.7 (4)

C2—C1—C6—C5 −0.4 (3) N2—C8—C13—C14 −0.3 (3)

N1—C1—C6—C5 179.3 (2) C7—C8—C13—C14 177.3 (2)

C4—C5—C6—C1 1.6 (3) C8—C13—C14—C15 4.0 (3)

C9—N1—C7—O1 −179.7 (2) C8—C13—C14—C19 −175.1 (2)

C1—N1—C7—O1 −1.5 (3) C19—C14—C15—C16 −0.3 (3)

C9—N1—C7—C8 −0.3 (2) C13—C14—C15—C16 −179.4 (2)

C1—N1—C7—C8 178.0 (2) C14—C15—C16—C17 −0.6 (3)

C9—N2—C8—C13 176.4 (2) C15—C16—C17—C18 0.9 (3)

C9—N2—C8—C7 −1.5 (2) C16—C17—C18—C19 −0.3 (3)

O1—C7—C8—C13 2.5 (3) C17—C18—C19—C14 −0.7 (3)

N1—C7—C8—C13 −176.9 (2) C15—C14—C19—C18 1.0 (3)

O1—C7—C8—N2 −179.5 (2) C13—C14—C19—C18 −179.9 (2)

Hydrogen-bond geometry (Å, º)

D—H···A D—H H···A D···A D—H···A

N3—H3n···O1i 0.86 2.15 2.926 (2) 150

N3—H3n′···O1i 0.86 2.36 2.926 (2) 124

Figure

Figure 1

References

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In this paper, we pro- pose an imitation learning framework for non- autoregressive machine translation, which still enjoys the fast translation speed but gives comparable

Our adaptation method, ASADA , is shown in Fig- ure 2 : a) A model with a joint vocabulary is first pre-trained on artificial titles for the unlabeled tar- get domain (Section 3.2 ).

A lo largo de estos once años, se pueden destacar tres momentos clave, y que son los que con carácter general se toman como referencia: el segundo trimestre de 2008, cuando se

This research was conducted to observe the influence of Brand Image, Promotion, and Distribution on Purchasing Decision of chemical compound fertilizer of white pepper farmers in