3-Methyl-5-phenyl-1-(3-phenyl­isoquinolin-1-yl)-1H-pyrazole

Khan, F.N.; Manivel, P.; Kone, S.; Hathwar, V.R.; Ng, S.W.

doi:10.1107/S160053680905572X

organic compounds

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ISSN: 2056-9890

Volume 66| Part 2| February 2010| Page o368

https://doi.org/10.1107/S160053680905572X

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3-Methyl-5-phenyl-1-(3-phenylisoquinolin-1-yl)-1H-pyrazole

F. Nawaz Khan,^a P. Manivel,^a Sriramakrishnaswamy Kone,^a Venkatesha R. Hathwar ^b and Seik Weng Ng ^c ^*

^aChemistry Division, School of Advanced Sciences, VIT University, Vellore 632014, Tamil Nadu, India, ^bSolid State and Structural Chemistry Unit, Indian Institute of Science, Bangalore 560012, Karnataka, India, and ^cDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
^*Correspondence e-mail: seikweng@um.edu.my

(Received 28 December 2009; accepted 30 December 2009; online 16 January 2010)

The title compound, C₂₅H₁₉N₃, is composed of an aryl-substituted pyrazole ring connected to an aryl-substituted isoquinoline ring system with a dihedral angle of 52.7 (1)° between the pyrazole ring and the isoquinoline ring system. The dihedral angle between the pyrazole ring and the phenyl ring attached to it is 27.4 (1)° and the dihedral angle between the isoquinoline ring system and the phenyl ring attached to it is 19.6 (1)°.

Related literature

For medicinal applications of hydrazine derivatives, see: Broadhurst et al. (2001 ).

Experimental

Crystal data

C₂₅H₁₉N₃
M_r = 361.43
Orthorhombic, P b c a
a = 10.9610 (9) Å
b = 16.8078 (13) Å
c = 21.3118 (17) Å
V = 3926.3 (5) Å³
Z = 8
Mo Kα radiation
μ = 0.07 mm⁻¹
T = 290 K
0.42 × 0.23 × 0.20 mm

Data collection

Bruker SMART area-detector diffractometer
26302 measured reflections
3452 independent reflections
2031 reflections with I > 2σ(I)
R_int = 0.091

Refinement

R[F² > 2σ(F²)] = 0.059
wR(F²) = 0.172
S = 1.04
3452 reflections
254 parameters
H-atom parameters constrained
Δρ_max = 0.16 e Å⁻³
Δρ_min = −0.16 e Å⁻³

Data collection: SMART (Bruker, 2004 ); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: X-SEED (Barbour, 2001 ); software used to prepare material for publication: publCIF (Westrip, 2010 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S160053680905572X/bt5159sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S160053680905572X/bt5159Isup2.hkl

checkCIF report

Related literature top

For medicinal applications of hydrazine derivatives, see: Broadhurst et al. (2001).

Experimental top

3-Phenylisoquinolin-1-ylhydrazine (2.35 g, 10 mmol) and 1-phenylbutane-1,3-dione (1.62 g, 10 mmol) were dissolved in ethanol (30 ml). The solution was heated for 12 h under a nitrogen atmosphere. The reaction was quenched with water; the compound was extracted with ethyl acetate. The ethyl acetate phase was washed with water, dried, concentrated and purified by column chromatography to yield a white powder. Crystals were obtained upon recrystallization from dichloromethane.

Structure description top

For medicinal applications of hydrazine derivatives, see: Broadhurst et al. (2001).

Computing details top

Data collection: SMART (Bruker, 2004); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT (Bruker, 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: X-SEED (Barbour, 2001); software used to prepare material for publication: publCIF (Westrip, 2010).

Figures top

Fig. 1. Anisotropic displacement ellipsoid plot (Barbour, 2001) of C₂₅H₁₉N₃ at the 50% probability level; hydrogen atoms are drawn as spheres of arbitrary radius.

3-Methyl-5-phenyl-1-(3-phenylisoquinolin-1-yl)-1H-pyrazole top

Crystal data top

C₂₅H₁₉N₃	F(000) = 1520
M_r = 361.43	D_x = 1.223 Mg m⁻³
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 1667 reflections
a = 10.9610 (9) Å	θ = 2.4–19.5°
b = 16.8078 (13) Å	µ = 0.07 mm⁻¹
c = 21.3118 (17) Å	T = 290 K
V = 3926.3 (5) Å³	Block, colorless
Z = 8	0.42 × 0.23 × 0.20 mm

Data collection top

Bruker SMART area-detector diffractometer	2031 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.091
Graphite monochromator	θ_max = 25.0°, θ_min = 1.9°
φ and ω scans	h = −13→13
26302 measured reflections	k = −19→19
3452 independent reflections	l = −25→25

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)] = 0.059	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.172	H-atom parameters constrained
S = 1.04	w = 1/[σ²(F_o²) + (0.0822P)² + 0.3609P] where P = (F_o² + 2F_c²)/3
3452 reflections	(Δ/σ)_max = 0.001
254 parameters	Δρ_max = 0.16 e Å⁻³
0 restraints	Δρ_min = −0.16 e Å⁻³

Crystal data top

C₂₅H₁₉N₃	V = 3926.3 (5) Å³
M_r = 361.43	Z = 8
Orthorhombic, Pbca	Mo Kα radiation
a = 10.9610 (9) Å	µ = 0.07 mm⁻¹
b = 16.8078 (13) Å	T = 290 K
c = 21.3118 (17) Å	0.42 × 0.23 × 0.20 mm

Data collection top

Bruker SMART area-detector diffractometer	2031 reflections with I > 2σ(I)
26302 measured reflections	R_int = 0.091
3452 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.059	0 restraints
wR(F²) = 0.172	H-atom parameters constrained
S = 1.04	Δρ_max = 0.16 e Å⁻³
3452 reflections	Δρ_min = −0.16 e Å⁻³
254 parameters

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

	x	y	z	U_iso*/U_eq
N1	0.42399 (17)	0.56804 (11)	0.65341 (8)	0.0632 (5)
N2	0.58627 (17)	0.61748 (12)	0.59624 (9)	0.0707 (6)
N3	0.70861 (18)	0.60123 (14)	0.60212 (10)	0.0846 (7)
C1	0.5164 (2)	0.61722 (15)	0.65309 (11)	0.0634 (6)
C2	0.5528 (2)	0.66672 (14)	0.70362 (11)	0.0633 (6)
C3	0.6493 (2)	0.72259 (17)	0.70207 (14)	0.0799 (8)
H3	0.6940	0.7293	0.6654	0.096*
C4	0.6771 (3)	0.76627 (17)	0.75330 (18)	0.0925 (9)
H4	0.7414	0.8023	0.7517	0.111*
C5	0.6101 (3)	0.75780 (18)	0.80879 (16)	0.0963 (9)
H5	0.6304	0.7881	0.8438	0.116*
C6	0.5156 (3)	0.70560 (18)	0.81196 (14)	0.0876 (8)
H6	0.4713	0.7006	0.8490	0.105*
C7	0.4844 (2)	0.65902 (14)	0.75938 (11)	0.0681 (6)
C8	0.3851 (2)	0.60570 (14)	0.75944 (11)	0.0691 (7)
H8	0.3392	0.5993	0.7958	0.083*
C9	0.3554 (2)	0.56334 (14)	0.70713 (11)	0.0617 (6)
C10	0.2482 (2)	0.50980 (14)	0.70392 (11)	0.0635 (6)
C11	0.1918 (2)	0.48178 (15)	0.75749 (12)	0.0745 (7)
H11	0.2226	0.4958	0.7966	0.089*
C12	0.0904 (3)	0.43317 (16)	0.75384 (15)	0.0858 (8)
H12	0.0538	0.4149	0.7905	0.103*
C13	0.0441 (3)	0.4121 (2)	0.69771 (17)	0.0999 (10)
H13	−0.0241	0.3793	0.6955	0.120*
C14	0.0978 (3)	0.4392 (2)	0.64406 (16)	0.1194 (12)
H14	0.0660	0.4248	0.6052	0.143*
C15	0.1993 (3)	0.4880 (2)	0.64698 (13)	0.0944 (9)
H15	0.2350	0.5062	0.6101	0.113*
C16	0.8797 (3)	0.5726 (3)	0.53211 (16)	0.1305 (13)
H16A	0.9202	0.5639	0.5715	0.196*
H16B	0.9171	0.6166	0.5108	0.196*
H16C	0.8864	0.5257	0.5067	0.196*
C17	0.7463 (2)	0.59087 (19)	0.54383 (14)	0.0888 (8)
C18	0.6524 (3)	0.59926 (17)	0.50078 (13)	0.0849 (8)
H18	0.6579	0.5946	0.4574	0.102*
C19	0.5500 (2)	0.61580 (14)	0.53516 (12)	0.0688 (7)
C20	0.4262 (2)	0.63444 (15)	0.51195 (12)	0.0700 (7)
C21	0.3472 (3)	0.68436 (17)	0.54353 (13)	0.0869 (8)
H21	0.3704	0.7068	0.5816	0.104*
C22	0.2326 (3)	0.7011 (2)	0.51841 (16)	0.1031 (10)
H22	0.1792	0.7335	0.5407	0.124*
C23	0.1976 (3)	0.6712 (2)	0.46237 (18)	0.1081 (10)
H23	0.1214	0.6835	0.4458	0.130*
C24	0.2752 (3)	0.6231 (2)	0.43068 (16)	0.1117 (11)
H24	0.2522	0.6027	0.3919	0.134*
C25	0.3885 (3)	0.60395 (18)	0.45521 (13)	0.0887 (8)
H25	0.4398	0.5700	0.4330	0.106*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N1	0.0544 (11)	0.0749 (13)	0.0603 (12)	0.0075 (10)	0.0015 (10)	0.0039 (9)
N2	0.0542 (12)	0.0933 (15)	0.0646 (13)	0.0066 (11)	0.0042 (10)	0.0105 (10)
N3	0.0552 (13)	0.1212 (19)	0.0773 (15)	0.0096 (12)	0.0066 (11)	0.0139 (13)
C1	0.0534 (13)	0.0770 (16)	0.0598 (15)	0.0118 (13)	0.0008 (11)	0.0094 (12)
C2	0.0553 (14)	0.0668 (15)	0.0679 (16)	0.0089 (12)	−0.0046 (12)	0.0053 (12)
C3	0.0663 (16)	0.0801 (18)	0.093 (2)	0.0056 (15)	−0.0055 (14)	0.0093 (15)
C4	0.0795 (19)	0.0796 (19)	0.118 (3)	−0.0061 (15)	−0.0244 (19)	0.0043 (19)
C5	0.100 (2)	0.090 (2)	0.099 (3)	0.0029 (19)	−0.0241 (19)	−0.0117 (17)
C6	0.091 (2)	0.091 (2)	0.081 (2)	0.0016 (18)	−0.0062 (15)	−0.0128 (15)
C7	0.0642 (14)	0.0718 (15)	0.0682 (17)	0.0086 (13)	−0.0041 (13)	−0.0033 (13)
C8	0.0652 (15)	0.0802 (17)	0.0619 (16)	0.0128 (13)	0.0063 (12)	−0.0027 (13)
C9	0.0550 (13)	0.0701 (15)	0.0600 (15)	0.0128 (12)	0.0043 (11)	0.0010 (12)
C10	0.0557 (13)	0.0697 (15)	0.0652 (16)	0.0103 (12)	0.0054 (12)	−0.0026 (12)
C11	0.0721 (16)	0.0797 (17)	0.0717 (17)	0.0030 (14)	0.0063 (14)	0.0030 (13)
C12	0.0782 (18)	0.0835 (18)	0.096 (2)	0.0000 (15)	0.0207 (17)	0.0067 (16)
C13	0.076 (2)	0.113 (2)	0.110 (3)	−0.0224 (17)	0.0062 (18)	−0.002 (2)
C14	0.102 (2)	0.164 (3)	0.092 (2)	−0.051 (2)	−0.0043 (19)	−0.012 (2)
C15	0.0830 (18)	0.129 (3)	0.0713 (18)	−0.0221 (18)	0.0066 (15)	−0.0034 (17)
C16	0.0710 (19)	0.202 (4)	0.119 (3)	0.025 (2)	0.0287 (18)	0.014 (3)
C17	0.0685 (17)	0.121 (2)	0.0765 (19)	0.0118 (16)	0.0171 (15)	0.0141 (17)
C18	0.0853 (19)	0.106 (2)	0.0633 (16)	0.0106 (16)	0.0141 (15)	0.0110 (14)
C19	0.0733 (16)	0.0701 (16)	0.0630 (16)	0.0038 (13)	0.0045 (13)	0.0093 (12)
C20	0.0748 (16)	0.0685 (15)	0.0667 (17)	0.0027 (13)	0.0002 (14)	0.0110 (12)
C21	0.091 (2)	0.093 (2)	0.0768 (18)	0.0228 (17)	−0.0073 (15)	0.0028 (14)
C22	0.097 (2)	0.121 (3)	0.091 (2)	0.0377 (19)	−0.0039 (19)	0.0170 (18)
C23	0.084 (2)	0.144 (3)	0.097 (3)	0.017 (2)	−0.0086 (19)	0.022 (2)
C24	0.101 (2)	0.145 (3)	0.089 (2)	−0.005 (2)	−0.024 (2)	−0.004 (2)
C25	0.089 (2)	0.102 (2)	0.0748 (19)	0.0065 (17)	−0.0030 (16)	−0.0044 (15)

Geometric parameters (Å, º) top

N1—C1	1.308 (3)	C12—H12	0.9300
N1—C9	1.372 (3)	C13—C14	1.365 (4)
N2—C19	1.362 (3)	C13—H13	0.9300
N2—N3	1.374 (3)	C14—C15	1.383 (4)
N2—C1	1.433 (3)	C14—H14	0.9300
N3—C17	1.321 (3)	C15—H15	0.9300
C1—C2	1.418 (3)	C16—C17	1.515 (4)
C2—C7	1.411 (3)	C16—H16A	0.9600
C2—C3	1.414 (3)	C16—H16B	0.9600
C3—C4	1.351 (4)	C16—H16C	0.9600
C3—H3	0.9300	C17—C18	1.385 (4)
C4—C5	1.399 (4)	C18—C19	1.370 (3)
C4—H4	0.9300	C18—H18	0.9300
C5—C6	1.359 (4)	C19—C20	1.478 (3)
C5—H5	0.9300	C20—C25	1.377 (3)
C6—C7	1.409 (3)	C20—C21	1.381 (4)
C6—H6	0.9300	C21—C22	1.394 (4)
C7—C8	1.410 (3)	C21—H21	0.9300
C8—C9	1.362 (3)	C22—C23	1.351 (4)
C8—H8	0.9300	C22—H22	0.9300
C9—C10	1.481 (3)	C23—C24	1.355 (5)
C10—C15	1.376 (3)	C23—H23	0.9300
C10—C11	1.381 (3)	C24—C25	1.385 (4)
C11—C12	1.382 (4)	C24—H24	0.9300
C11—H11	0.9300	C25—H25	0.9300
C12—C13	1.347 (4)

C1—N1—C9	117.7 (2)	C12—C13—H13	120.2
C19—N2—N3	111.61 (19)	C14—C13—H13	120.2
C19—N2—C1	130.7 (2)	C13—C14—C15	120.5 (3)
N3—N2—C1	116.34 (19)	C13—C14—H14	119.7
C17—N3—N2	104.2 (2)	C15—C14—H14	119.8
N1—C1—C2	125.8 (2)	C10—C15—C14	120.7 (3)
N1—C1—N2	114.9 (2)	C10—C15—H15	119.6
C2—C1—N2	119.3 (2)	C14—C15—H15	119.6
C7—C2—C3	118.5 (2)	C17—C16—H16A	109.5
C7—C2—C1	115.9 (2)	C17—C16—H16B	109.5
C3—C2—C1	125.6 (2)	H16A—C16—H16B	109.5
C4—C3—C2	120.7 (3)	C17—C16—H16C	109.5
C4—C3—H3	119.6	H16A—C16—H16C	109.5
C2—C3—H3	119.6	H16B—C16—H16C	109.5
C3—C4—C5	120.6 (3)	N3—C17—C18	112.2 (2)
C3—C4—H4	119.7	N3—C17—C16	118.9 (3)
C5—C4—H4	119.7	C18—C17—C16	128.9 (3)
C6—C5—C4	120.5 (3)	C19—C18—C17	106.0 (2)
C6—C5—H5	119.7	C19—C18—H18	127.0
C4—C5—H5	119.7	C17—C18—H18	127.0
C5—C6—C7	120.3 (3)	N2—C19—C18	106.0 (2)
C5—C6—H6	119.9	N2—C19—C20	125.7 (2)
C7—C6—H6	119.9	C18—C19—C20	128.1 (2)
C8—C7—C2	118.0 (2)	C25—C20—C21	117.8 (3)
C8—C7—C6	122.7 (2)	C25—C20—C19	119.4 (2)
C2—C7—C6	119.3 (2)	C21—C20—C19	122.8 (2)
C9—C8—C7	121.1 (2)	C20—C21—C22	120.0 (3)
C9—C8—H8	119.5	C20—C21—H21	120.0
C7—C8—H8	119.5	C22—C21—H21	120.0
C8—C9—N1	121.5 (2)	C23—C22—C21	121.4 (3)
C8—C9—C10	123.0 (2)	C23—C22—H22	119.3
N1—C9—C10	115.5 (2)	C21—C22—H22	119.3
C15—C10—C11	117.6 (2)	C22—C23—C24	118.9 (3)
C15—C10—C9	120.8 (2)	C22—C23—H23	120.5
C11—C10—C9	121.6 (2)	C24—C23—H23	120.5
C12—C11—C10	121.0 (2)	C23—C24—C25	120.9 (3)
C12—C11—H11	119.5	C23—C24—H24	119.5
C10—C11—H11	119.5	C25—C24—H24	119.5
C13—C12—C11	120.6 (3)	C20—C25—C24	120.9 (3)
C13—C12—H12	119.7	C20—C25—H25	119.5
C11—C12—H12	119.7	C24—C25—H25	119.5
C12—C13—C14	119.6 (3)

C19—N2—N3—C17	0.9 (3)	N1—C9—C10—C11	161.5 (2)
C1—N2—N3—C17	169.0 (2)	C15—C10—C11—C12	0.4 (4)
C9—N1—C1—C2	0.0 (3)	C9—C10—C11—C12	178.7 (2)
C9—N1—C1—N2	178.25 (18)	C10—C11—C12—C13	−0.1 (4)
C19—N2—C1—N1	42.3 (3)	C11—C12—C13—C14	−0.1 (5)
N3—N2—C1—N1	−123.0 (2)	C12—C13—C14—C15	0.1 (5)
C19—N2—C1—C2	−139.3 (2)	C11—C10—C15—C14	−0.4 (4)
N3—N2—C1—C2	55.3 (3)	C9—C10—C15—C14	−178.7 (3)
N1—C1—C2—C7	2.4 (3)	C13—C14—C15—C10	0.2 (5)
N2—C1—C2—C7	−175.80 (18)	N2—N3—C17—C18	−0.5 (3)
N1—C1—C2—C3	−176.8 (2)	N2—N3—C17—C16	179.2 (3)
N2—C1—C2—C3	5.1 (3)	N3—C17—C18—C19	−0.1 (3)
C7—C2—C3—C4	1.6 (3)	C16—C17—C18—C19	−179.8 (3)
C1—C2—C3—C4	−179.3 (2)	N3—N2—C19—C18	−1.0 (3)
C2—C3—C4—C5	−0.8 (4)	C1—N2—C19—C18	−166.9 (2)
C3—C4—C5—C6	−0.2 (4)	N3—N2—C19—C20	−176.8 (2)
C4—C5—C6—C7	0.4 (4)	C1—N2—C19—C20	17.3 (4)
C3—C2—C7—C8	177.2 (2)	C17—C18—C19—N2	0.6 (3)
C1—C2—C7—C8	−2.0 (3)	C17—C18—C19—C20	176.3 (3)
C3—C2—C7—C6	−1.4 (3)	N2—C19—C20—C25	−156.5 (2)
C1—C2—C7—C6	179.4 (2)	C18—C19—C20—C25	28.6 (4)
C5—C6—C7—C8	−178.1 (2)	N2—C19—C20—C21	26.4 (4)
C5—C6—C7—C2	0.4 (4)	C18—C19—C20—C21	−148.5 (3)
C2—C7—C8—C9	−0.5 (3)	C25—C20—C21—C22	1.3 (4)
C6—C7—C8—C9	178.0 (2)	C19—C20—C21—C22	178.5 (2)
C7—C8—C9—N1	3.1 (3)	C20—C21—C22—C23	−2.0 (5)
C7—C8—C9—C10	−176.8 (2)	C21—C22—C23—C24	1.0 (5)
C1—N1—C9—C8	−2.8 (3)	C22—C23—C24—C25	0.6 (6)
C1—N1—C9—C10	177.05 (19)	C21—C20—C25—C24	0.3 (4)
C8—C9—C10—C15	159.6 (2)	C19—C20—C25—C24	−177.0 (3)
N1—C9—C10—C15	−20.2 (3)	C23—C24—C25—C20	−1.2 (5)
C8—C9—C10—C11	−18.6 (3)

Experimental details

Crystal data
Chemical formula	C₂₅H₁₉N₃
M_r	361.43
Crystal system, space group	Orthorhombic, Pbca
Temperature (K)	290
a, b, c (Å)	10.9610 (9), 16.8078 (13), 21.3118 (17)
V (Å³)	3926.3 (5)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.07
Crystal size (mm)	0.42 × 0.23 × 0.20

Data collection
Diffractometer	Bruker SMART area-detector diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	26302, 3452, 2031
R_int	0.091
(sin θ/λ)_max (Å⁻¹)	0.594

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.059, 0.172, 1.04
No. of reflections	3452
No. of parameters	254
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.16, −0.16

Computer programs: SMART (Bruker, 2004), SAINT (Bruker, 2004), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), X-SEED (Barbour, 2001), publCIF (Westrip, 2010).

Acknowledgements

We thank the Department of Science and Technology, India, for use of the diffraction facility at IISc under the IRHPA–DST program. FNK thanks the DST for Fast Track Proposal funding. We thank VIT University and the University of Malaya for supporting this study.

References

Barbour, L. J. (2001). J. Supramol. Chem. 1, 189–191. CrossRef CAS Google Scholar
Broadhurst, M. J., Johnson, W. H. & Walter, D. S. (2001). US Patent No. 6235787. Google Scholar
Bruker (2004). SAINT and SMART. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Westrip, S. P. (2010). publCIF. In preparation. Google Scholar