Correlation of structural and physico-chemical parameters with the bioactivity of alkylated derivatives of indole-3-acetic acid, a phytohormone (auxin)

Nigović, B.; Antolić, S.; Kojić-Prodić, B.; Kiralj, R.; Magnus, V.; Salopek-Sondi, B.

doi:10.1107/S0108768199006199

Correlation of structural and physico-chemical parameters with the bioactivity of alkylated derivatives of indole-3-acetic acid, a phytohormone (auxin)

B. Nigovic, S. Antolic, B. Kojic-Prodic, R. Kiralj, V. Magnus and B. Salopek-Sondi

As part of molecular recognition studies on the phytohormone indole-3-acetic acid (IAA) a series of alkylated IAAs has been examined. Phenyl-ring substitution (alkyl = methyl and ethyl) at positions 4-, 6- or 7- as well as pyrrole substitution at the 2- site resulted in the six compounds which are analyzed: 2-Me-IAA, 4-Me-IAA, 6-Me-IAA, 7-Me-IAA, 4-Et-IAA and 6-Et-IAA. The structure-activity relationships investigated include those between the geometrical parameters of the molecular structures determined by X-ray analysis, the growth-promoting activities in the Avena coleoptile straight-growth bioassay and relative lipophilicities calculated from retention times on a reversed-phase HPLC column and from R_F values in reversed-phase TLC. Lipophilicities are correlated with the moments of inertia, average polarizability, molecular mass, and the van der Waals radii of the ring substituents. The influence of substitution on the electronic properties of the indole ring and its geometry is discussed on the basis of the UV and ¹H NMR spectra.

Keywords: Indole-3-acetic acid; Phytohormone; Bioactivity; Molecular recognition studies.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S0108768199006199/ha0181sup1.cif Contains datablocks global, 2-Me-IAA, 4-Me-IAA, 6-Me-IAA, 7-Me-IAA, 4-Et-IAA, 6-Et-IAA, iaalt
	Structure factor file (SHELXL table format) https://doi.org/10.1107/S0108768199006199/ha01812-Me-IAAsup2.sft Supplementary material
	Structure factor file (SHELXL table format) https://doi.org/10.1107/S0108768199006199/ha01814-Et-IAAsup3.sft Supplementary material
	Structure factor file (SHELXL table format) https://doi.org/10.1107/S0108768199006199/ha01814-Me-IAAsup4.sft Supplementary material
	Structure factor file (SHELXL table format) https://doi.org/10.1107/S0108768199006199/ha01816-Et-IAAsup5.sft Supplementary material
	Structure factor file (SHELXL table format) https://doi.org/10.1107/S0108768199006199/ha01816-Me-IAAsup6.sft Supplementary material
	Structure factor file (SHELXL table format) https://doi.org/10.1107/S0108768199006199/ha01817-Me-IAAsup7.sft Supplementary material

CCDC references: 141651; 141652; 141653; 141654; 141655; 141656; 141657

Computing details top

For all compounds, data collection: CAD4 (Enraf Nonius 1988) software; cell refinement: CAD4 (Enraf Nonius 1988) software <CELDIM> routine; data reduction: SDP (Frenz, 1982). Program(s) used to solve structure: SHELXS86 (Sheldrick,1985, 1990) for 2-Me-IAA, 4-Me-IAA, 6-Me-IAA, 7-Me-IAA, 4-Et-IAA, 6-Et-IAA; SHELX86 (Sheldrick,1985) for iaalt. For all compounds, program(s) used to refine structure: SHELX76 (Sheldrick, 1976); molecular graphics: PLATON93 (Spek, 1982, 1990) & ORTEP (Johnson, 1965), PLUTON93 (Spek 1991); software used to prepare material for publication: PLATON93 (Spek 1982, 1990).

(2-Me-IAA) 2-methyl-idole-3-acetic acid top

Crystal data top

C₁₁H₁₁NO₂	F(000) = 400
M_r = 189.21	D_x = 1.289 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
a = 8.542 (1) Å	Cell parameters from 25 reflections
b = 13.408 (1) Å	θ = 7–18°
c = 8.638 (1) Å	µ = 0.09 mm⁻¹
β = 99.70 (1)°	T = 297 K
V = 975.18 (8) Å³	Prismatic, colourless
Z = 4	0.40 × 0.15 × 0.15 mm

Data collection top

Enraf-Nonius CAD4 diffractometer	R_int = 0.013
Radiation source: fine-focus sealed tube	θ_max = 25°, θ_min = 2°
Graphite monochromator	h = 0→10
ω/2θ scans	k = 0→15
1920 measured reflections	l = −10→10
1467 independent reflections	3 standard reflections every 87 reflections
1052 reflections with I > 3σ(I)	intensity decay: 0.3%

Refinement top

Refinement on F	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: difference Fourier map
wR(F²) = 0.043	All H-atom parameters refined except Uiso for H101, H102, H103
1052 reflections	Calculated w = 1.4784/[σ²(F_o) + 0.001075(F_o²)]
168 parameters	(Δ/σ)_max = 0.05
0 restraints	Δρ_max = 0.17 e Å⁻³
0 constraints	Δρ_min = −0.18 e Å⁻³

Special details top

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All e.s.d.'s are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

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

	x	y	z	U_iso*/U_eq
O1	0.9544 (2)	−0.0794 (1)	0.8285 (2)	0.0583 (6)
O2	0.8698 (2)	0.0681 (1)	0.8907 (2)	0.0692 (7)
N1	0.5467 (3)	0.2278 (2)	0.5059 (2)	0.0568 (7)
C2	0.6732 (3)	0.1639 (2)	0.5051 (2)	0.0502 (8)
C3	0.6586 (3)	0.0868 (2)	0.6046 (2)	0.0468 (7)
C4	0.4384 (4)	0.0496 (2)	0.7716 (3)	0.0617 (10)
C5	0.2965 (4)	0.0862 (3)	0.8023 (4)	0.0774 (13)
C6	0.2313 (4)	0.1739 (3)	0.7354 (4)	0.0779 (13)
C7	0.3063 (3)	0.2276 (2)	0.6360 (3)	0.0667 (10)
C8	0.7676 (4)	0.0000 (2)	0.6379 (3)	0.0569 (9)
C9	0.8678 (3)	0.0001 (2)	0.7971 (3)	0.0446 (7)
C10	0.7939 (4)	0.1848 (2)	0.4057 (4)	0.0760 (11)
C31	0.5171 (3)	0.1024 (2)	0.6679 (2)	0.0483 (7)
C71	0.4486 (3)	0.1914 (2)	0.6023 (2)	0.0504 (8)
H1	0.531 (3)	0.282 (2)	0.443 (3)	0.078 (9)*
H4	0.485 (3)	−0.015 (2)	0.816 (3)	0.079 (9)*
H5	0.249 (4)	0.052 (2)	0.871 (3)	0.083 (10)*
H6	0.125 (4)	0.197 (2)	0.762 (4)	0.103 (11)*
H7	0.260 (4)	0.291 (2)	0.590 (4)	0.095 (10)*
H11	1.017 (4)	−0.075 (2)	0.938 (4)	0.097 (10)*
H81	0.847 (3)	−0.0034 (19)	0.567 (3)	0.069 (8)*
H82	0.714 (3)	−0.062 (2)	0.632 (3)	0.081 (9)*
H101	0.870 (5)	0.132 (3)	0.401 (5)	0.1500*
H102	0.750 (5)	0.190 (3)	0.295 (6)	0.1500*
H103	0.854 (5)	0.234 (4)	0.430 (6)	0.1500*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0610 (11)	0.0482 (10)	0.0593 (11)	0.0132 (8)	−0.0083 (9)	−0.0045 (7)
O2	0.0845 (13)	0.0579 (11)	0.0543 (10)	0.0241 (9)	−0.0194 (9)	−0.0124 (8)
N1	0.0704 (14)	0.0503 (12)	0.0469 (11)	0.0153 (11)	0.0021 (11)	0.0074 (10)
C2	0.0584 (15)	0.0511 (13)	0.0382 (12)	0.0034 (12)	0.0000 (11)	−0.0028 (10)
C3	0.0556 (15)	0.0450 (12)	0.0351 (11)	0.0046 (10)	−0.0060 (11)	−0.0049 (9)
C4	0.0748 (19)	0.0615 (17)	0.0470 (15)	−0.0136 (15)	0.0048 (14)	−0.0031 (12)
C5	0.075 (2)	0.104 (3)	0.0560 (17)	−0.029 (2)	0.0191 (16)	−0.0158 (17)
C6	0.0612 (19)	0.108 (3)	0.0606 (18)	0.0063 (19)	−0.0013 (16)	−0.0189 (18)
C7	0.0662 (18)	0.083 (2)	0.0468 (15)	0.0159 (16)	−0.0021 (14)	−0.0108 (14)
C8	0.0688 (18)	0.0523 (15)	0.0445 (14)	0.0123 (14)	−0.0049 (13)	−0.0056 (12)
C9	0.0464 (13)	0.0396 (11)	0.0462 (12)	0.0017 (10)	0.0032 (10)	0.0008 (10)
C10	0.084 (2)	0.075 (2)	0.0733 (19)	0.0008 (16)	0.0258 (18)	0.0059 (16)
C31	0.0557 (14)	0.0498 (13)	0.0346 (11)	−0.0009 (11)	−0.0063 (10)	−0.006 (1)
C71	0.0536 (15)	0.0603 (15)	0.0338 (11)	0.0075 (12)	−0.0029 (11)	−0.0059 (10)

Geometric parameters (Å, º) top

O1—C9	1.300 (3)	C8—C9	1.492 (4)
O2—C9	1.217 (3)	C31—C71	1.406 (4)
N1—C2	1.380 (4)	O1—H11	1.01 (3)
N1—C71	1.367 (3)	N1—H1	0.90 (3)
C2—C3	1.363 (3)	C4—H4	1.00 (3)
C2—C10	1.475 (4)	C5—H5	0.90 (3)
C3—C8	1.488 (4)	C6—H6	1.02 (3)
C3—C31	1.424 (4)	C7—H7	0.99 (3)
C4—C5	1.374 (5)	C8—H81	0.99 (3)
C4—C31	1.399 (4)	C8—H82	0.95 (3)
C5—C6	1.385 (5)	C10—H101	0.97 (4)
C6—C7	1.361 (4)	C10—H102	0.97 (5)
C7—C71	1.385 (4)	C10—H103	0.84 (5)

C2—N1—C71	110.0 (2)	C2—N1—H1	122.2 (17)
N1—C2—C3	108.2 (2)	C71—N1—H1	127.5 (17)
N1—C2—C10	120.6 (2)	C5—C4—H4	122.8 (15)
C3—C2—C10	131.1 (2)	C31—C4—H4	118.7 (15)
C2—C3—C8	126.5 (2)	C4—C5—H5	117 (2)
C2—C3—C31	107.7 (2)	C6—C5—H5	121 (2)
C8—C3—C31	125.8 (2)	C5—C6—H6	118.3 (17)
C5—C4—C31	118.5 (3)	C7—C6—H6	120.8 (17)
C4—C5—C6	121.9 (3)	C6—C7—H7	121 (2)
C5—C6—C7	120.9 (3)	C71—C7—H7	121 (2)
C6—C7—C71	118.1 (3)	C3—C8—H81	112.9 (15)
C3—C8—C9	114.9 (2)	C3—C8—H82	113.3 (16)
O1—C9—O2	122.1 (2)	C9—C8—H81	102.9 (15)
O1—C9—C8	114.2 (2)	C9—C8—H82	104.3 (16)
O2—C9—C8	123.7 (2)	H81—C8—H82	108 (2)
C3—C31—C4	134.6 (3)	C2—C10—H101	115 (3)
C3—C31—C71	107.0 (2)	C2—C10—H102	113 (3)
C4—C31—C71	118.4 (2)	C2—C10—H103	117 (3)
N1—C71—C7	130.8 (2)	H101—C10—H102	99 (4)
N1—C71—C31	107.0 (2)	H101—C10—H103	101 (4)
C7—C71—C31	122.2 (2)	H102—C10—H103	108 (4)
C9—O1—H11	110.0 (16)

C71—N1—C2—C3	−1.4 (3)	C31—C4—C5—C6	−0.9 (5)
C71—N1—C2—C10	178.0 (2)	C5—C4—C31—C3	−177.3 (3)
C2—N1—C71—C7	−177.7 (2)	C5—C4—C31—C71	1.2 (4)
C2—N1—C71—C31	1.4 (3)	C4—C5—C6—C7	−0.1 (7)
N1—C2—C3—C8	179.1 (2)	C5—C6—C7—C71	0.8 (5)
N1—C2—C3—C31	0.8 (3)	C6—C7—C71—N1	178.5 (3)
C10—C2—C3—C8	−0.2 (4)	C6—C7—C71—C31	−0.4 (4)
C10—C2—C3—C31	−178.5 (3)	C3—C8—C9—O1	175.5 (2)
C2—C3—C8—C9	108.5 (3)	C3—C8—C9—O2	−4.5 (4)
C31—C3—C8—C9	−73.6 (3)	C3—C31—C71—N1	−0.8 (2)
C2—C3—C31—C4	178.6 (3)	C3—C31—C71—C7	178.4 (2)
C2—C3—C31—C71	0.0 (9)	C4—C31—C71—N1	−179.7 (2)
C8—C3—C31—C4	0.4 (4)	C4—C31—C71—C7	−0.5 (3)
C8—C3—C31—C71	−178.2 (2)

(4-Me-IAA) 4-methyl-indole-3-acetic acid top

Crystal data top

C₁₁H₁₁NO₂	F(000) = 400
M_r = 189.21	D_x = 1.290 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
a = 8.680 (1) Å	Cell parameters from 25 reflections
b = 7.624 (1) Å	θ = 6–18°
c = 15.044 (1) Å	µ = 0.09 mm⁻¹
β = 101.870 (6)°	T = 103 K
V = 974.27 (8) Å³	Prismatic, colourless
Z = 4	0.50 × 0.25 × 0.20 mm

Data collection top

Enraf-Nonius CAD4 diffractometer	R_int = 0.040
Radiation source: fine-focus sealed tube	θ_max = 25°, θ_min = 2°
Graphite monochromator	h = 0→10
ω/2θ scans	k = 0→9
1974 measured reflections	l = −17→17
1619 independent reflections	3 standard reflections every 87 reflections
1434 reflections with I > 3σ(I)	intensity decay: 0.5%

Refinement top

Refinement on F	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.035	Hydrogen site location: difference Fourier map
wR(F²) = 0.041	All H-atom parameters refined except H1, H11 normalized
1434 reflections	Calculated w = 1.4555/[σ²(F_o) + 0.001021(F_o²)]
172 parameters	(Δ/σ)_max = 0.005
0 restraints	Δρ_max = 0.23 e Å⁻³
0 constraints	Δρ_min = −0.24 e Å⁻³

Special details top

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

	x	y	z	U_iso*/U_eq
O1	0.5521 (1)	0.2131 (1)	1.0514 (1)	0.0212 (3)
O2	0.5873 (1)	0.0922 (1)	0.9217 (1)	0.0189 (3)
N1	0.8154 (1)	0.4957 (2)	0.7507 (1)	0.0235 (4)
C2	0.6982 (2)	0.4966 (2)	0.7990 (1)	0.0241 (5)
C3	0.7464 (2)	0.4108 (2)	0.8795 (1)	0.0201 (4)
C4	1.0201 (2)	0.2654 (2)	0.9475 (1)	0.0233 (4)
C5	1.1639 (2)	0.2323 (2)	0.9242 (1)	0.0292 (5)
C6	1.1989 (2)	0.2872 (2)	0.8416 (1)	0.0286 (5)
C7	1.0911 (2)	0.3783 (2)	0.7789 (1)	0.0228 (4)
C8	0.6513 (2)	0.3986 (2)	0.9518 (1)	0.0257 (5)
C9	0.5967 (2)	0.2191 (2)	0.9725 (1)	0.0170 (4)
C10	0.9912 (2)	0.2127 (2)	1.0392 (1)	0.0310 (5)
C31	0.9056 (2)	0.3534 (2)	0.8825 (1)	0.0180 (4)
C71	0.9440 (2)	0.4098 (2)	0.8000 (1)	0.0187 (4)
H1	0.813 (2)	0.550 (3)	0.6991 (13)	0.039 (5)*
H2	0.599 (2)	0.550 (2)	0.7756 (11)	0.023 (4)*
H5	1.245 (2)	0.178 (3)	0.9682 (12)	0.035 (5)*
H6	1.303 (2)	0.256 (2)	0.8280 (11)	0.031 (4)*
H7	1.1154 (18)	0.417 (2)	0.7205 (10)	0.023 (4)*
H11	0.511 (2)	0.112 (3)	1.0600 (13)	0.044 (6)*
H81	0.549 (2)	0.463 (3)	0.9334 (12)	0.041 (5)*
H82	0.711 (2)	0.449 (3)	1.0108 (12)	0.035 (5)*
H101	0.9035 (19)	0.128 (2)	1.0325 (11)	0.026 (4)*
H102	1.085 (2)	0.164 (3)	1.0746 (13)	0.045 (5)*
H103	0.953 (2)	0.315 (3)	1.0717 (12)	0.041 (5)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0347 (6)	0.0160 (5)	0.0172 (5)	−0.0044 (4)	0.0150 (4)	−0.0016 (4)
O2	0.0280 (5)	0.0147 (5)	0.0167 (5)	−0.0013 (4)	0.0107 (4)	−0.0015 (4)
N1	0.0289 (7)	0.0256 (7)	0.0185 (6)	0.0015 (5)	0.0105 (5)	0.0071 (5)
C2	0.0274 (8)	0.0205 (8)	0.0273 (8)	0.0029 (6)	0.0126 (6)	0.0059 (6)
C3	0.0319 (8)	0.0119 (7)	0.0202 (7)	−0.0023 (6)	0.0142 (6)	−0.0006 (5)
C4	0.0318 (8)	0.0155 (7)	0.0203 (7)	−0.0090 (6)	0.0003 (6)	0.0002 (6)
C5	0.0267 (8)	0.0221 (8)	0.0344 (9)	−0.0057 (6)	−0.0040 (7)	0.0064 (7)
C6	0.0233 (8)	0.0235 (8)	0.0392 (9)	−0.0030 (6)	0.0072 (7)	−0.0021 (7)
C7	0.0266 (8)	0.0226 (7)	0.0214 (7)	−0.0054 (6)	0.0104 (6)	−0.0049 (6)
C8	0.0419 (9)	0.0150 (7)	0.0268 (8)	−0.0008 (6)	0.0227 (7)	−0.0013 (6)
C9	0.0212 (7)	0.0170 (7)	0.0150 (6)	0.0018 (5)	0.0087 (5)	0.0007 (5)
C10	0.0427 (10)	0.0254 (9)	0.0214 (8)	−0.0114 (8)	−0.0013 (7)	0.0059 (7)
C31	0.0300 (8)	0.0098 (7)	0.0157 (6)	−0.0046 (6)	0.0079 (5)	−0.0028 (5)
C71	0.0258 (8)	0.0148 (7)	0.0164 (7)	−0.0029 (6)	0.0062 (5)	−0.0012 (5)

Geometric parameters (Å, º) top

O1—C9	1.323 (2)	C8—C9	1.502 (2)
O2—C9	1.2252 (19)	C31—C71	1.417 (2)
N1—C2	1.366 (2)	O1—H11	0.87 (2)
N1—C71	1.373 (2)	N1—H1	0.88 (2)
C2—C3	1.364 (2)	C2—H2	0.952 (17)
C3—C8	1.497 (2)	C5—H5	0.956 (19)
C3—C31	1.441 (2)	C6—H6	0.995 (18)
C4—C5	1.387 (2)	C7—H7	0.990 (15)
C4—C10	1.507 (2)	C8—H81	1.003 (19)
C4—C31	1.412 (2)	C8—H82	1.007 (19)
C5—C6	1.402 (2)	C10—H101	0.987 (16)
C6—C7	1.373 (2)	C10—H102	0.952 (19)
C7—C71	1.398 (2)	C10—H103	1.01 (2)

C2—N1—C71	109.07 (14)	C2—N1—H1	125.7 (12)
N1—C2—C3	110.10 (15)	C71—N1—H1	124.9 (12)
C2—C3—C8	124.08 (15)	N1—C2—H2	121.4 (10)
C2—C3—C31	106.88 (14)	C3—C2—H2	128.5 (10)
C8—C3—C31	128.80 (14)	C4—C5—H5	118.5 (11)
C5—C4—C10	120.72 (14)	C6—C5—H5	118.7 (11)
C5—C4—C31	116.94 (14)	C5—C6—H6	118.8 (9)
C10—C4—C31	122.33 (15)	C7—C6—H6	119.9 (9)
C4—C5—C6	122.66 (15)	C6—C7—H7	121.4 (9)
C5—C6—C7	121.23 (16)	C71—C7—H7	121.4 (9)
C6—C7—C71	117.13 (14)	C3—C8—H81	111 (1)
C3—C8—C9	116.86 (13)	C3—C8—H82	110.8 (10)
O1—C9—O2	122.56 (14)	C9—C8—H81	101.8 (12)
O1—C9—C8	112.38 (12)	C9—C8—H82	107.0 (12)
O2—C9—C8	125.00 (14)	H81—C8—H82	108.8 (16)
C3—C31—C4	134.39 (15)	C4—C10—H101	110.5 (10)
C3—C31—C71	106.10 (13)	C4—C10—H102	109.4 (11)
C4—C31—C71	119.47 (16)	C4—C10—H103	111.7 (11)
N1—C71—C7	129.66 (14)	H101—C10—H102	110.8 (16)
N1—C71—C31	107.85 (14)	H101—C10—H103	103.4 (14)
C7—C71—C31	122.49 (15)	H102—C10—H103	111.0 (16)
C9—O1—H11	111.6 (13)

C71—N1—C2—C3	−0.6 (2)	C5—C4—C31—C71	−2.8 (2)
C2—N1—C71—C7	−179.15 (15)	C10—C4—C31—C3	−1.6 (3)
C2—N1—C71—C31	0.4 (2)	C10—C4—C31—C71	175.75 (14)
N1—C2—C3—C8	175.38 (14)	C4—C5—C6—C7	0.2 (2)
N1—C2—C3—C31	0.60 (18)	C5—C6—C7—C71	−1.6 (2)
C2—C3—C8—C9	115.29 (18)	C6—C7—C71—N1	−179.79 (15)
C31—C3—C8—C9	−71.1 (2)	C6—C7—C71—C31	0.7 (2)
C2—C3—C31—C4	177.28 (17)	C3—C8—C9—O1	162.95 (14)
C2—C3—C31—C71	−0.36 (17)	C3—C8—C9—O2	−19.9 (2)
C8—C3—C31—C4	2.8 (3)	C3—C31—C71—N1	0.0 (4)
C8—C3—C31—C71	−174.81 (15)	C3—C31—C71—C7	179.56 (14)
C10—C4—C5—C6	−176.55 (14)	C4—C31—C71—N1	−178.07 (14)
C31—C4—C5—C6	2.0 (2)	C4—C31—C71—C7	1.5 (2)
C5—C4—C31—C3	179.82 (18)

(6-Me-IAA) 6-Methyl-indole-3-acetic acid top

Crystal data top

C₁₁H₁₁NO₂	F(000) = 800
M_r = 189.21	D_x = 1.304 Mg m⁻³
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 25 reflections
a = 6.216 (1) Å	θ = 6–17°
b = 38.627 (1) Å	µ = 0.09 mm⁻¹
c = 8.031 (1) Å	T = 297 K
V = 1928.29 (18) Å³	Prismatic, colourless
Z = 8	0.50 × 0.40 × 0.40 mm

Data collection top

Enraf-Nonius CAD4 diffractometer	R_int = 0.050
Radiation source: fine-focus sealed tube	θ_max = 25°, θ_min = 2°
Graphite monochromator	h = 0→7
ω/2θ scans	k = 0→46
2040 measured reflections	l = 0→9
1398 independent reflections	3 standard reflections every 87 reflections
970 reflections with I > 3σ(I)	intensity decay: 1.8%

Refinement top

Refinement on F	3 constraints
Least-squares matrix: full	All H-atom parameters refined, except H101, H102, H103 parameters constrained, H1 normalized, H81, H82 riding
R[F² > 2σ(F²)] = 0.049	Calculated w = 3.7308/[σ²(F_o) + 0.000000(F_o²)]
wR(F²) = 0.041	(Δ/σ)_max = 0.05
970 reflections	Δρ_max = 0.16 e Å⁻³
158 parameters	Δρ_min = −0.19 e Å⁻³
0 restraints

Special details top

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

	x	y	z	U_iso*/U_eq
O1	0.0216 (5)	0.5280 (1)	1.1766 (3)	0.0625 (11)
O2	0.1625 (4)	0.5298 (1)	0.9238 (3)	0.0650 (11)
N1	0.7320 (6)	0.5899 (1)	0.8783 (4)	0.0530 (14)
C2	0.5665 (6)	0.5693 (1)	0.9324 (4)	0.0423 (12)
C3	0.4239 (5)	0.5887 (1)	1.0198 (4)	0.0366 (11)
C4	0.4350 (7)	0.6546 (1)	1.0885 (5)	0.0510 (16)
C5	0.5540 (7)	0.6840 (1)	1.0622 (5)	0.0607 (17)
C6	0.7456 (7)	0.6836 (1)	0.9691 (5)	0.0623 (17)
C7	0.8196 (7)	0.6530 (1)	0.9022 (5)	0.0560 (16)
C8	0.2243 (5)	0.5776 (1)	1.1089 (4)	0.0423 (12)
C9	0.1367 (6)	0.5429 (1)	1.0610 (5)	0.0453 (12)
C10	0.8722 (8)	0.7168 (1)	0.9436 (6)	0.094 (2)
C31	0.5057 (5)	0.6232 (1)	1.0204 (4)	0.0394 (11)
C71	0.6987 (5)	0.6234 (1)	0.9290 (4)	0.0426 (14)
H1	0.806 (6)	0.5835 (8)	0.812 (4)	0.050 (14)*
H2	0.560 (5)	0.5446 (9)	0.907 (3)	0.041 (10)*
H4	0.305 (5)	0.6558 (7)	1.148 (3)	0.033 (9)*
H5	0.498 (5)	0.7083 (8)	1.111 (3)	0.054 (10)*
H7	0.950 (6)	0.6495 (9)	0.839 (4)	0.074 (13)*
H11	−0.058 (7)	0.5037 (12)	1.141 (5)	0.115 (16)*
H81	0.1012 (5)	0.5967 (1)	1.0851 (4)	0.096 (14)*
H82	0.2598 (5)	0.5770 (1)	1.2405 (4)	0.082 (12)*
H101	0.8020 (8)	0.7376 (1)	1.0151 (6)	0.1500*
H102	0.8720 (8)	0.7237 (1)	0.8132 (6)	0.1500*
H103	1.0356 (8)	0.7126 (1)	0.9844 (6)	0.1500*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.075 (2)	0.0618 (19)	0.0507 (16)	−0.0250 (17)	0.0161 (15)	−0.0061 (13)
O2	0.085 (2)	0.0646 (19)	0.0455 (16)	−0.0251 (16)	0.0119 (16)	−0.0136 (14)
N1	0.045 (2)	0.068 (3)	0.046 (2)	0.006 (2)	0.0124 (19)	−0.0100 (19)
C2	0.044 (2)	0.045 (2)	0.038 (2)	0.004 (2)	−0.0024 (19)	−0.004 (2)
C3	0.0353 (19)	0.043 (2)	0.0316 (18)	0.0003 (19)	−0.0045 (17)	−0.0011 (17)
C4	0.041 (2)	0.056 (3)	0.056 (3)	0.004 (2)	0.008 (2)	−0.003 (2)
C5	0.058 (3)	0.051 (3)	0.073 (3)	0.004 (2)	0.007 (3)	−0.002 (2)
C6	0.058 (3)	0.061 (3)	0.068 (3)	−0.010 (2)	−0.002 (3)	0.010 (2)
C7	0.043 (2)	0.073 (3)	0.052 (3)	−0.005 (2)	0.007 (2)	0.005 (2)
C8	0.039 (2)	0.044 (2)	0.044 (2)	−0.0011 (18)	0.0016 (18)	−0.0042 (17)
C9	0.042 (2)	0.049 (2)	0.045 (2)	0.0017 (19)	−0.004 (2)	0.004 (2)
C10	0.088 (4)	0.074 (3)	0.119 (4)	−0.030 (3)	0.012 (3)	0.011 (3)
C31	0.0346 (19)	0.049 (2)	0.0345 (19)	0.0053 (17)	0.0002 (18)	0.0033 (17)
C71	0.039 (2)	0.053 (3)	0.0359 (19)	0.001 (2)	−0.0004 (19)	0.0030 (19)

Geometric parameters (Å, º) top

O1—C9	1.306 (5)	C8—C9	1.497 (5)
O2—C9	1.223 (5)	C31—C71	1.406 (4)
N1—C2	1.371 (5)	O1—H11	1.10 (5)
N1—C71	1.372 (5)	N1—H1	0.75 (3)
C2—C3	1.356 (5)	C2—H2	0.98 (3)
C3—C8	1.495 (5)	C4—H4	0.94 (3)
C3—C31	1.426 (5)	C5—H5	1.08 (3)
C4—C5	1.372 (6)	C7—H7	0.97 (4)
C4—C31	1.401 (5)	C8—H81	1.080 (5)
C5—C6	1.406 (6)	C8—H82	1.080 (5)
C6—C7	1.377 (6)	C10—H101	1.080 (6)
C6—C10	1.518 (6)	C10—H102	1.081 (7)
C7—C71	1.385 (5)	C10—H103	1.079 (7)

C2—N1—C71	109.9 (3)	C2—N1—H1	120 (3)
N1—C2—C3	109.5 (3)	C71—N1—H1	128 (2)
C2—C3—C8	129.2 (4)	N1—C2—H2	122.1 (18)
C2—C3—C31	106.6 (3)	C3—C2—H2	128.4 (18)
C8—C3—C31	124.2 (3)	C5—C4—H4	120.1 (17)
C5—C4—C31	119.2 (4)	C31—C4—H4	120.7 (17)
C4—C5—C6	122.0 (4)	C4—C5—H5	119.5 (16)
C5—C6—C7	120.0 (4)	C6—C5—H5	118.5 (16)
C5—C6—C10	120.1 (4)	C6—C7—H7	127 (2)
C7—C6—C10	119.9 (4)	C71—C7—H7	115 (2)
C6—C7—C71	117.8 (4)	C3—C8—H81	107.9 (4)
C3—C8—C9	115.8 (3)	C3—C8—H82	107.8 (3)
O1—C9—O2	122.0 (4)	C9—C8—H81	108.0 (3)
O1—C9—C8	114.3 (3)	C9—C8—H82	107.9 (4)
O2—C9—C8	123.7 (4)	H81—C8—H82	109.4 (4)
C3—C31—C4	134.3 (3)	C6—C10—H101	110.3 (5)
C3—C31—C71	107.9 (3)	C6—C10—H102	109.8 (4)
C4—C31—C71	117.8 (3)	C6—C10—H103	108.6 (4)
N1—C71—C7	130.6 (3)	H101—C10—H102	109.4 (5)
N1—C71—C31	106.2 (3)	H101—C10—H103	109.3 (5)
C7—C71—C31	123.3 (4)	H102—C10—H103	109.4 (6)
C9—O1—H11	116 (2)

C71—N1—C2—C3	−0.5 (4)	C5—C4—C31—C71	0.7 (5)
C2—N1—C71—C7	−179.0 (4)	C4—C5—C6—C7	−0.5 (6)
C2—N1—C71—C31	0.9 (4)	C4—C5—C6—C10	−179.9 (4)
N1—C2—C3—C8	−177.1 (3)	C5—C6—C7—C71	0.5 (6)
N1—C2—C3—C31	−0.2 (4)	C10—C6—C7—C71	179.9 (5)
C2—C3—C8—C9	−17.7 (5)	C6—C7—C71—N1	179.9 (5)
C31—C3—C8—C9	166.0 (3)	C6—C7—C71—C31	0.0 (11)
C2—C3—C31—C4	−179.8 (5)	C3—C8—C9—O1	154.8 (3)
C2—C3—C31—C71	0.7 (4)	C3—C8—C9—O2	−27.8 (5)
C8—C3—C31—C4	−2.7 (6)	C3—C31—C71—N1	−1.0 (4)
C8—C3—C31—C71	177.8 (3)	C3—C31—C71—C7	178.9 (3)
C31—C4—C5—C6	−0.2 (7)	C4—C31—C71—N1	179.4 (3)
C5—C4—C31—C3	−178.8 (4)	C4—C31—C71—C7	−0.7 (5)

(7-Me-IAA) 7-Methyl-indole-3-acetic acid top

Crystal data top

C₁₁H₁₁NO₂	F(000) = 400
M_r = 189.21	D_x = 1.317 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
a = 19.353 (1) Å	Cell parameters from 25 reflections
b = 5.074 (1) Å	θ = 6–17°
c = 10.275 (1) Å	µ = 0.09 mm⁻¹
β = 109.000 (6)°	T = 297 K
V = 954.00 (9) Å³	Prismatic, colorless
Z = 4	0.40 × 0.30 × 0.10 mm

Data collection top

Enraf-Nonius CAD4 diffractometer	R_int = 0.013
Radiation source: fine-focus sealed tube	θ_max = 25°, θ_min = 2°
Graphite monochromator	h = −22→21
ω/2θ scans	k = 0→6
1988 measured reflections	l = 0→12
1461 independent reflections	3 standard reflections every 87 reflections
1038 reflections with I > 3σ(I)	intensity decay: 0.1%

Refinement top

Refinement on F	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.041	Hydrogen site location: difference Fourier map
wR(F²) = 0.036	Refall, except H1, H11 normalized
1038 reflections	Calculated w = 2.6240/[σ²(F_o) + 0.000000(F_o²)]
172 parameters	(Δ/σ)_max = 0.05
0 restraints	Δρ_max = 0.14 e Å⁻³
0 constraints	Δρ_min = −0.15 e Å⁻³

Special details top

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

	x	y	z	U_iso*/U_eq
O1	0.0107 (1)	0.7574 (4)	0.3874 (2)	0.0811 (6)
O2	0.0766 (1)	0.4041 (4)	0.4752 (2)	0.0743 (6)
N1	0.2671 (1)	0.2538 (4)	0.3218 (2)	0.0542 (6)
C2	0.1960 (1)	0.3372 (5)	0.2674 (3)	0.0565 (7)
C3	0.1828 (1)	0.5300 (5)	0.3466 (3)	0.0508 (6)
C4	0.2704 (1)	0.7386 (5)	0.5714 (3)	0.0616 (7)
C5	0.3411 (1)	0.7287 (6)	0.6591 (3)	0.0680 (7)
C6	0.3916 (1)	0.5545 (5)	0.6355 (3)	0.0637 (7)
C7	0.3736 (1)	0.3841 (5)	0.5252 (2)	0.0500 (6)
C8	0.1134 (1)	0.6829 (5)	0.3196 (3)	0.0629 (7)
C9	0.0662 (1)	0.5992 (5)	0.4035 (3)	0.0552 (7)
C10	0.4284 (2)	0.2032 (6)	0.4975 (3)	0.0720 (7)
C31	0.2490 (1)	0.5697 (5)	0.4581 (2)	0.0467 (6)
C71	0.3014 (1)	0.3938 (5)	0.4391 (2)	0.0452 (6)
H1	0.2890 (9)	0.1306 (15)	0.2899 (13)	0.0578 (16)*
H2	0.1641 (8)	0.2645 (15)	0.1797 (13)	0.0567 (16)*
H4	0.2357 (8)	0.8717 (15)	0.5833 (13)	0.0566 (16)*
H5	0.3579 (9)	0.8613 (15)	0.7394 (13)	0.0648 (16)*
H6	0.4425 (9)	0.5556 (15)	0.6959 (13)	0.0578 (16)*
H11	−0.0165 (9)	0.6858 (15)	0.4279 (13)	0.0677 (16)*
H81	0.1225 (9)	0.8800 (15)	0.3356 (13)	0.0641 (16)*
H82	0.0810 (9)	0.6662 (15)	0.2215 (13)	0.0571 (16)*
H101	0.4362 (9)	0.2409 (15)	0.4103 (13)	0.0625 (16)*
H102	0.4088 (9)	0.0325 (15)	0.4775 (13)	0.0647 (16)*
H103	0.4772 (8)	0.2306 (15)	0.5713 (13)	0.0681 (16)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0686 (9)	0.0768 (10)	0.1205 (11)	0.0191 (9)	0.0617 (9)	0.0362 (10)
O2	0.0600 (9)	0.0844 (11)	0.0921 (10)	0.0192 (9)	0.0434 (8)	0.0401 (10)
N1	0.0614 (10)	0.0485 (10)	0.0613 (10)	0.0011 (10)	0.0318 (9)	−0.0057 (10)
C2	0.0554 (11)	0.0601 (12)	0.0579 (12)	−0.0123 (10)	0.0238 (10)	0.0022 (11)
C3	0.0505 (10)	0.0506 (12)	0.0616 (11)	−0.0027 (10)	0.0322 (10)	0.0081 (11)
C4	0.0755 (12)	0.0517 (12)	0.0749 (12)	−0.0022 (11)	0.0482 (10)	−0.0052 (11)
C5	0.0857 (12)	0.0649 (12)	0.0638 (12)	−0.0202 (12)	0.0387 (11)	−0.0177 (11)
C6	0.0615 (11)	0.0744 (13)	0.0584 (12)	−0.0098 (11)	0.024 (1)	0.0032 (12)
C7	0.0549 (11)	0.0514 (11)	0.0506 (11)	0.0007 (10)	0.0265 (10)	0.0080 (11)
C8	0.0552 (11)	0.0650 (13)	0.0787 (12)	0.0017 (11)	0.036 (1)	0.0179 (12)
C9	0.0417 (10)	0.0624 (12)	0.0643 (12)	0.0012 (11)	0.0212 (10)	0.0048 (12)
C10	0.0644 (12)	0.0791 (13)	0.0767 (12)	0.0117 (12)	0.0286 (11)	0.0047 (12)
C31	0.0563 (10)	0.0400 (11)	0.0560 (11)	−0.0047 (10)	0.0349 (9)	−0.0001 (10)
C71	0.0556 (11)	0.0392 (11)	0.0507 (11)	−0.0031 (10)	0.0308 (9)	0.0023 (10)

Geometric parameters (Å, º) top

O1—C9	1.308 (3)	C8—C9	1.507 (3)
O2—C9	1.211 (3)	C31—C71	1.411 (3)
N1—C2	1.373 (3)	O1—H11	0.851 (16)
N1—C71	1.370 (3)	N1—H1	0.877 (13)
C2—C3	1.349 (4)	C2—H2	0.983 (13)
C3—C8	1.497 (3)	C4—H4	0.988 (13)
C3—C31	1.428 (3)	C5—H5	1.032 (11)
C4—C5	1.373 (4)	C6—H6	0.979 (16)
C4—C31	1.395 (4)	C8—H81	1.019 (8)
C5—C6	1.396 (3)	C8—H82	1.002 (13)
C6—C7	1.377 (4)	C10—H101	0.975 (14)
C7—C10	1.498 (4)	C10—H102	0.941 (10)
C7—C71	1.390 (3)	C10—H103	1.010 (15)

C2—N1—C71	109.4 (2)	C2—N1—H1	127.6 (10)
N1—C2—C3	109.8 (2)	C71—N1—H1	123 (1)
C2—C3—C8	126.8 (2)	N1—C2—H2	120.3 (8)
C2—C3—C31	106.8 (2)	C3—C2—H2	129.7 (8)
C8—C3—C31	126.3 (2)	C5—C4—H4	121.1 (8)
C5—C4—C31	119.1 (2)	C31—C4—H4	119.6 (8)
C4—C5—C6	120.9 (3)	C4—C5—H5	119.2 (9)
C5—C6—C7	122.5 (2)	C6—C5—H5	119.7 (10)
C6—C7—C10	122.4 (2)	C5—C6—H6	120.2 (7)
C6—C7—C71	115.7 (2)	C7—C6—H6	117.3 (7)
C10—C7—C71	121.9 (2)	C3—C8—H81	112.4 (10)
C3—C8—C9	115.0 (2)	C3—C8—H82	111.9 (9)
O1—C9—O2	123.1 (2)	C9—C8—H81	106.8 (9)
O1—C9—C8	112.4 (2)	C9—C8—H82	104.7 (10)
O2—C9—C8	124.5 (2)	H81—C8—H82	105.3 (9)
C3—C31—C4	134.5 (2)	C7—C10—H101	112.7 (8)
C3—C31—C71	107.29 (19)	C7—C10—H102	110.2 (11)
C4—C31—C71	118.18 (19)	C7—C10—H103	108.6 (7)
N1—C71—C7	129.8 (2)	H101—C10—H102	98.7 (10)
N1—C71—C31	106.58 (18)	H101—C10—H103	106.0 (13)
C7—C71—C31	123.6 (2)	H102—C10—H103	120.2 (10)
C9—O1—H11	106.8 (9)

C71—N1—C2—C3	0.1 (3)	C4—C5—C6—C7	−0.4 (4)
C2—N1—C71—C7	−177.4 (2)	C5—C6—C7—C10	178.0 (3)
C2—N1—C71—C31	0.4 (3)	C5—C6—C7—C71	−0.7 (4)
N1—C2—C3—C8	176.7 (2)	C6—C7—C71—N1	179.2 (2)
N1—C2—C3—C31	−0.5 (3)	C6—C7—C71—C31	1.8 (3)
C2—C3—C8—C9	102.5 (3)	C10—C7—C71—N1	0.4 (4)
C31—C3—C8—C9	−80.8 (3)	C10—C7—C71—C31	−177.0 (2)
C2—C3—C31—C4	179.4 (3)	C3—C8—C9—O1	172.8 (2)
C2—C3—C31—C71	0.7 (3)	C3—C8—C9—O2	−9.2 (4)
C8—C3—C31—C4	2.1 (4)	C3—C31—C71—N1	−0.7 (3)
C8—C3—C31—C71	−176.5 (2)	C3—C31—C71—C7	177.3 (2)
C31—C4—C5—C6	0.6 (4)	C4—C31—C71—N1	−179.6 (2)
C5—C4—C31—C3	−178.2 (3)	C4—C31—C71—C7	−1.6 (4)
C5—C4—C31—C71	0.3 (4)

(4-Et-IAA) 4-ethyl-indole-3-acetic acid top

Crystal data top

C₁₂H₁₃NO₂	F(000) = 432
M_r = 203.24	D_x = 1.360 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
a = 9.288 (1) Å	Cell parameters from 25 reflections
b = 7.440 (1) Å	θ = 6–18°
c = 14.776 (1) Å	µ = 0.09 mm⁻¹
β = 103.530 (6)°	T = 297 K
V = 992.72 (8) Å³	Plate, colourless
Z = 4	0.45 × 0.20 × 0.06 mm

Data collection top

Enraf-Nonius CAD4 diffractometer	R_int = 0.018
Radiation source: fine-focus sealed tube	θ_max = 25°, θ_min = 2°
Graphite monochromator	h = −1→11
ω/2θ scans	k = −1→8
2594 measured reflections	l = −17→17
1526 independent reflections	3 standard reflections every 87 reflections
999 reflections with I > 3σ(I)	intensity decay: 1.5%

Refinement top

Refinement on F	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.042	Hydrogen site location: difference Fourier map
wR(F²) = 0.046	All H-atom parameters refined
999 reflections	Calculated w = 0.8494/[σ²(F_o) + 0.002474(F_o²)]
188 parameters	(Δ/σ)_max = 0.010
0 restraints	Δρ_max = 0.02 e Å⁻³
0 constraints	Δρ_min = −0.02 e Å⁻³

Special details top

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

	x	y	z	U_iso*/U_eq
O1	0.0901 (3)	0.9177 (4)	−0.0898 (1)	0.0447 (8)
O2	0.1554 (2)	0.9165 (3)	0.0643 (1)	0.0427 (8)
N1	0.5646 (3)	0.7035 (4)	0.2082 (2)	0.0370 (9)
C2	0.4349 (4)	0.7608 (5)	0.1510 (2)	0.0338 (10)
C3	0.4470 (3)	0.7643 (4)	0.0610 (2)	0.0272 (9)
C4	0.6774 (3)	0.6834 (4)	−0.0070 (2)	0.0298 (10)
C5	0.8228 (4)	0.6282 (5)	0.0230 (2)	0.0384 (11)
C6	0.8888 (4)	0.5939 (5)	0.1171 (2)	0.0440 (11)
C7	0.8109 (4)	0.6144 (5)	0.1843 (2)	0.0411 (11)
C8	0.3287 (3)	0.8145 (5)	−0.0238 (2)	0.0297 (10)
C9	0.1852 (3)	0.8867 (4)	−0.0098 (2)	0.0283 (9)
C10	0.6073 (4)	0.7177 (5)	−0.1083 (2)	0.0327 (10)
C11	0.7026 (5)	0.6843 (7)	−0.1775 (2)	0.0465 (14)
C31	0.5956 (3)	0.7070 (4)	0.0616 (2)	0.0277 (9)
C71	0.6651 (3)	0.6708 (4)	0.1556 (2)	0.031 (1)
H1	0.576 (4)	0.678 (5)	0.270 (3)	0.052 (11)*
H2	0.355 (4)	0.786 (4)	0.1734 (19)	0.027 (8)*
H5	0.881 (4)	0.610 (5)	−0.020 (2)	0.043 (10)*
H6	0.998 (4)	0.561 (5)	0.133 (2)	0.052 (10)*
H7	0.858 (4)	0.595 (5)	0.247 (2)	0.049 (10)*
H11	0.002 (5)	0.972 (6)	−0.078 (3)	0.079 (14)*
H81	0.362 (3)	0.916 (4)	−0.059 (2)	0.034 (8)*
H82	0.307 (4)	0.708 (5)	−0.072 (3)	0.059 (11)*
H101	0.521 (4)	0.642 (4)	−0.127 (2)	0.034 (9)*
H102	0.570 (4)	0.848 (5)	−0.114 (2)	0.041 (9)*
H111	0.639 (4)	0.713 (5)	−0.245 (3)	0.059 (11)*
H112	0.737 (5)	0.564 (7)	−0.172 (3)	0.072 (14)*
H113	0.801 (5)	0.765 (6)	−0.163 (3)	0.072 (13)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0331 (13)	0.0699 (18)	0.0287 (11)	0.0197 (13)	0.0025 (10)	−0.0057 (11)
O2	0.0321 (12)	0.0669 (17)	0.0307 (12)	0.0139 (13)	0.0104 (10)	−0.0028 (11)
N1	0.0419 (17)	0.0455 (18)	0.0225 (13)	0.0048 (14)	0.0056 (12)	0.0015 (12)
C2	0.0314 (17)	0.0426 (19)	0.0301 (15)	0.0038 (16)	0.0124 (13)	0.0000 (14)
C3	0.0296 (15)	0.0255 (16)	0.0275 (14)	−0.0007 (14)	0.0084 (12)	−0.0014 (13)
C4	0.0299 (17)	0.0265 (17)	0.0338 (16)	−0.0020 (14)	0.0092 (13)	−0.0016 (12)
C5	0.0312 (19)	0.042 (2)	0.0433 (18)	0.0042 (16)	0.0113 (15)	−0.0041 (16)
C6	0.0272 (18)	0.054 (2)	0.0469 (19)	0.0065 (19)	0.0009 (15)	−0.0053 (17)
C7	0.0367 (19)	0.045 (2)	0.0353 (18)	0.0036 (18)	−0.0043 (16)	−0.0010 (16)
C8	0.0292 (17)	0.0357 (19)	0.0251 (14)	0.0024 (15)	0.0083 (13)	0.0002 (14)
C9	0.0274 (17)	0.0294 (16)	0.0283 (15)	−0.0004 (14)	0.0072 (13)	−0.0021 (13)
C10	0.0290 (17)	0.037 (2)	0.0334 (16)	0.0010 (17)	0.0099 (13)	0.0006 (14)
C11	0.043 (2)	0.065 (3)	0.0365 (19)	0.002 (2)	0.0192 (17)	−0.0015 (17)
C31	0.0273 (15)	0.0255 (17)	0.0299 (15)	0.0010 (14)	0.0057 (12)	−0.0013 (12)
C71	0.0319 (17)	0.0332 (18)	0.0271 (15)	−0.0010 (15)	0.0053 (13)	−0.0036 (13)

Geometric parameters (Å, º) top

O1—C9	1.320 (3)	C31—C71	1.414 (4)
O2—C9	1.211 (3)	O1—H11	0.96 (5)
N1—C2	1.368 (5)	N1—H1	0.91 (4)
N1—C71	1.369 (4)	C2—H2	0.90 (4)
C2—C3	1.361 (4)	C5—H5	0.94 (3)
C3—C8	1.508 (4)	C6—H6	1.02 (4)
C3—C31	1.443 (4)	C7—H7	0.94 (3)
C4—C5	1.382 (5)	C8—H81	1.01 (3)
C4—C10	1.508 (4)	C8—H82	1.05 (4)
C4—C31	1.413 (4)	C10—H101	0.97 (3)
C5—C6	1.405 (4)	C10—H102	1.03 (4)
C6—C7	1.367 (5)	C11—H111	1.06 (4)
C7—C71	1.386 (5)	C11—H112	0.95 (5)
C8—C9	1.496 (4)	C11—H113	1.07 (5)
C10—C11	1.521 (5)

C2—N1—C71	108.9 (3)	N1—C2—H2	121.4 (18)
N1—C2—C3	110.3 (3)	C3—C2—H2	128.2 (19)
C2—C3—C8	127.3 (3)	C4—C5—H5	120 (2)
C2—C3—C31	106.6 (3)	C6—C5—H5	117 (2)
C8—C3—C31	126.1 (3)	C5—C6—H6	117.0 (17)
C5—C4—C10	122.1 (3)	C7—C6—H6	121.9 (17)
C5—C4—C31	117.1 (3)	C6—C7—H7	120 (2)
C10—C4—C31	120.8 (3)	C71—C7—H7	123 (2)
C4—C5—C6	122.6 (3)	C3—C8—H81	111.3 (17)
C5—C6—C7	121.1 (3)	C3—C8—H82	111 (2)
C6—C7—C71	117.2 (3)	C9—C8—H81	101.2 (17)
C3—C8—C9	118.3 (2)	C9—C8—H82	109 (2)
O1—C9—O2	122.1 (3)	H81—C8—H82	104 (3)
O1—C9—C8	111.7 (2)	C4—C10—H101	108.8 (17)
O2—C9—C8	126.2 (3)	C4—C10—H102	107.5 (16)
C4—C10—C11	117.1 (3)	C11—C10—H101	106.7 (19)
C3—C31—C4	135.0 (3)	C11—C10—H102	109.7 (19)
C3—C31—C71	106.2 (2)	H101—C10—H102	107 (3)
C4—C31—C71	118.9 (3)	C10—C11—H111	108 (2)
N1—C71—C7	128.8 (3)	C10—C11—H112	110 (3)
N1—C71—C31	108.0 (3)	C10—C11—H113	112 (2)
C7—C71—C31	123.2 (3)	H111—C11—H112	112 (3)
C9—O1—H11	109 (3)	H111—C11—H113	110 (3)
C2—N1—H1	124 (2)	H112—C11—H113	105 (4)
C71—N1—H1	127 (2)

C71—N1—C2—C3	0.8 (4)	C5—C4—C31—C3	178.6 (3)
C2—N1—C71—C7	178.6 (3)	C5—C4—C31—C71	−0.9 (4)
C2—N1—C71—C31	−0.6 (4)	C10—C4—C31—C3	−1.4 (5)
N1—C2—C3—C8	178.3 (3)	C10—C4—C31—C71	179.1 (3)
N1—C2—C3—C31	−0.7 (4)	C4—C5—C6—C7	−0.2 (6)
C2—C3—C8—C9	6.7 (5)	C5—C6—C7—C71	−0.2 (5)
C31—C3—C8—C9	−174.6 (3)	C6—C7—C71—N1	−179.1 (3)
C2—C3—C31—C4	−179.3 (4)	C6—C7—C71—C31	0.0 (17)
C2—C3—C31—C71	0.3 (4)	C3—C8—C9—O1	−177.3 (3)
C8—C3—C31—C4	1.7 (6)	C3—C8—C9—O2	3.2 (5)
C8—C3—C31—C71	−178.7 (3)	C3—C31—C71—N1	0.2 (4)
C10—C4—C5—C6	−179.3 (3)	C3—C31—C71—C7	−179.1 (3)
C31—C4—C5—C6	0.8 (5)	C4—C31—C71—N1	179.9 (3)
C5—C4—C10—C11	1.5 (5)	C4—C31—C71—C7	0.6 (5)
C31—C4—C10—C11	−178.5 (3)

(6-Et-IAA) 6-ethyl-indole-3-acetic acid top

Crystal data top

C₁₂H₁₃NO₂	F(000) = 432
M_r = 203.24	D_x = 1.307 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
a = 22.455 (1) Å	Cell parameters from 25 reflections
b = 5.286 (1) Å	θ = 5–13°
c = 9.313 (1) Å	µ = 0.09 mm⁻¹
β = 110.89 (1)°	T = 103 K
V = 1032.76 (10) Å³	Plate, colourless
Z = 4	0.30 × 0.20 × 0.06 mm

Data collection top

Enraf-Nonius CAD4 diffractometer	R_int = 0.052
Radiation source: fine-focus sealed tube	θ_max = 25°, θ_min = 2°
Graphite monochromator	h = 0→50
ω/2θ scans	k = 0→9
2917 measured reflections	l = −7→7
1476 independent reflections	3 standard reflections every 87 reflections
814 reflections with I > 2σ(I)	intensity decay: 2.4%

Refinement top

Refinement on F	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.066	Hydrogen site location: difference Fourier map
wR(F²) = 0.052	All H-atom pleaced in stereochemically expected positions and treated as riding
S = 0.91	Calculated w = 3.3591/[σ²(F_o) + 0.000091(F_o²)]
814 reflections	(Δ/σ)_max = 0.05
153 parameters	Δρ_max = 0.23 e Å⁻³
0 restraints	Δρ_min = −0.28 e Å⁻³
0 constraints

Special details top

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

	x	y	z	U_iso*/U_eq
O1	0.4866 (2)	0.2564 (7)	0.6155 (4)	0.0544 (18)
O2	0.43424 (18)	−0.1004 (7)	0.5175 (4)	0.0542 (14)
N1	0.2633 (3)	−0.2782 (8)	0.6324 (6)	0.059 (2)
C2	0.3246 (4)	−0.1955 (10)	0.7080 (7)	0.059 (3)
C3	0.3359 (4)	0.0156 (10)	0.6321 (7)	0.055 (3)
C4	0.2588 (4)	0.2437 (11)	0.3877 (7)	0.052 (3)
C5	0.1982 (4)	0.2344 (11)	0.2821 (7)	0.058 (3)
C6	0.1543 (4)	0.0466 (10)	0.2855 (8)	0.055 (3)
C7	0.1724 (4)	−0.1369 (10)	0.3998 (7)	0.053 (3)
C8	0.3964 (3)	0.1657 (10)	0.6779 (7)	0.058 (3)
C9	0.4407 (3)	0.0919 (11)	0.5944 (6)	0.053 (3)
C10	0.0879 (4)	0.0487 (10)	0.1664 (8)	0.070 (3)
C11	0.0465 (4)	0.2574 (11)	0.1914 (9)	0.087 (4)
C31	0.2787 (4)	0.0611 (9)	0.5051 (7)	0.049 (3)
C71	0.2337 (4)	−0.1267 (10)	0.5067 (8)	0.056 (3)
H1	0.2430 (3)	−0.4279 (8)	0.6641 (6)	0.1500*
H2	0.3585 (4)	−0.2804 (10)	0.8100 (7)	0.051 (16)*
H4	0.2912 (4)	0.3903 (11)	0.3811 (7)	0.061 (16)*
H5	0.1835 (4)	0.3763 (11)	0.1928 (7)	0.042 (13)*
H7	0.1397 (4)	−0.2833 (10)	0.4048 (7)	0.058 (16)*
H11	0.521 (3)	0.210 (13)	0.570 (8)	0.1500*
H81	0.4216 (3)	0.1399 (10)	0.7997 (7)	0.060 (16)*
H82	0.3841 (3)	0.3627 (10)	0.6545 (7)	0.074 (16)*
H101	0.0655 (4)	−0.1308 (10)	0.1703 (8)	0.052 (15)*
H102	0.0913 (4)	0.0737 (10)	0.0545 (8)	0.12 (2)*
H111	−0.0016 (4)	0.2558 (11)	0.1087 (9)	0.08 (2)*
H112	0.0456 (4)	0.2237 (11)	0.3049 (9)	0.15 (3)*
H113	0.0680 (4)	0.4392 (11)	0.1888 (9)	0.11 (2)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.098 (4)	0.027 (2)	0.058 (3)	0.009 (3)	0.052 (3)	−0.002 (2)
O2	0.102 (3)	0.031 (2)	0.050 (2)	0.011 (2)	0.052 (2)	−0.009 (2)
N1	0.124 (5)	0.024 (3)	0.055 (4)	0.007 (3)	0.064 (4)	0.008 (3)
C2	0.122 (6)	0.026 (3)	0.050 (5)	0.026 (4)	0.057 (5)	0.008 (3)
C3	0.116 (6)	0.023 (3)	0.055 (5)	0.015 (4)	0.066 (5)	0.001 (3)
C4	0.113 (6)	0.019 (3)	0.055 (4)	−0.004 (4)	0.067 (4)	−0.007 (4)
C5	0.130 (6)	0.019 (3)	0.052 (4)	−0.001 (5)	0.067 (5)	0.003 (4)
C6	0.120 (6)	0.020 (3)	0.049 (4)	0.000 (4)	0.058 (5)	−0.005 (3)
C7	0.120 (6)	0.015 (3)	0.053 (4)	−0.003 (4)	0.066 (5)	−0.001 (3)
C8	0.116 (6)	0.028 (3)	0.058 (4)	0.008 (4)	0.064 (4)	−0.001 (3)
C9	0.107 (6)	0.032 (3)	0.037 (4)	0.022 (4)	0.045 (4)	0.014 (3)
C10	0.138 (7)	0.025 (4)	0.064 (5)	−0.020 (4)	0.056 (6)	−0.011 (4)
C11	0.110 (8)	0.033 (4)	0.097 (7)	−0.012 (5)	0.011 (6)	−0.017 (4)
C31	0.109 (6)	0.015 (3)	0.055 (4)	0.009 (4)	0.067 (4)	0.001 (3)
C71	0.127 (7)	0.016 (3)	0.055 (5)	0.007 (5)	0.068 (5)	0.002 (4)

Geometric parameters (Å, º) top

O1—C9	1.309 (8)	C8—C9	1.516 (9)
O2—C9	1.222 (7)	C10—C11	1.513 (11)
O1—H11	1.03 (7)	C31—C71	1.420 (11)
N1—C71	1.378 (8)	C2—H2	1.081 (9)
N1—C2	1.375 (11)	C4—H4	1.080 (11)
N1—H1	1.008 (8)	C5—H5	1.080 (8)
C2—C3	1.392 (9)	C7—H7	1.079 (11)
C3—C8	1.498 (10)	C8—H81	1.081 (9)
C3—C31	1.422 (10)	C8—H82	1.079 (8)
C4—C31	1.407 (8)	C10—H101	1.081 (9)
C4—C5	1.366 (11)	C10—H102	1.08 (1)
C5—C6	1.407 (11)	C11—H111	1.080 (12)
C6—C10	1.508 (12)	C11—H112	1.079 (11)
C6—C7	1.389 (8)	C11—H113	1.08 (1)
C7—C71	1.383 (12)

O1···C8ⁱ	3.418 (7)	H1···C5^vi	2.304 (9)
O1···C9ⁱ	3.157 (7)	H1···C6^vi	2.637 (11)
O1···O2ⁱⁱ	2.635 (6)	H1···C31^vi	3.032 (8)
O2···O1ⁱⁱ	2.635 (6)	H2···H82^v	2.565 (9)
O2···C2ⁱⁱⁱ	3.236 (8)	H2···H11^ix	2.53 (7)
O2···C9ⁱⁱ	3.326 (8)	H2···O2^vi	2.163 (8)
O1···H81^iv	2.832 (7)	H4···C2^iv	2.574 (10)
O1···H81ⁱ	2.797 (7)	H4···C3^iv	2.880 (11)
O2···H11ⁱⁱ	1.61 (7)	H5···H102	2.569 (11)
O2···H2ⁱⁱⁱ	2.163 (8)	H5···C7^iv	2.987 (9)
N1···C4^v	3.380 (8)	H5···C71^iv	2.724 (11)
N1···C4^vi	3.448 (8)	H7···H101	2.367 (10)
N1···C5^vi	3.369 (9)	H7···H113^v	2.546 (10)
C2···O2^vi	3.236 (8)	H7···H102^vi	2.562 (10)
C2···C4^vii	3.529 (10)	H11···H2ⁱ	2.53 (7)
C4···N1ⁱⁱⁱ	3.448 (8)	H11···O2ⁱⁱ	1.61 (7)
C4···N1^viii	3.380 (8)	H11···C9ⁱⁱ	2.56 (7)
C4···C2^iv	3.529 (10)	H11···H11ⁱⁱ	2.58 (10)
C5···N1ⁱⁱⁱ	3.369 (9)	H81···O1^ix	2.797 (7)
C8···O1^ix	3.418 (7)	H81···O1^vii	2.832 (7)
C9···O2ⁱⁱ	3.326 (8)	H81···C9^vii	2.981 (8)
C9···O1^ix	3.157 (7)	H82···C2^viii	2.822 (9)
C2···H82^v	2.822 (9)	H82···C4	3.082 (10)
C2···H4^vii	2.574 (10)	H82···H2^viii	2.565 (9)
C3···H4^vii	2.880 (11)	H101···H7	2.367 (10)
C4···H82	3.082 (10)	H101···H113^v	2.279 (8)
C4···H1ⁱⁱⁱ	2.537 (8)	H101···H111^x	2.567 (10)
C5···H113	2.943 (12)	H102···H5	2.569 (11)
C5···H1ⁱⁱⁱ	2.304 (9)	H102···H7ⁱⁱⁱ	2.562 (10)
C6···H1ⁱⁱⁱ	2.637 (11)	H102···H112^iv	2.429 (10)
C7···H5^vii	2.987 (9)	H111···C10^x	3.061 (10)
C9···H11ⁱⁱ	2.56 (7)	H111···H101^x	2.567 (10)
C9···H81^iv	2.981 (8)	H112···H102^vii	2.429 (10)
C10···H111^x	3.061 (10)	H113···C5	2.943 (12)
C31···H1ⁱⁱⁱ	3.032 (8)	H113···H7^viii	2.546 (10)
C71···H5^vii	2.724 (11)	H113···H101^viii	2.279 (8)
H1···C4^vi	2.537 (8)

C9—O1—H11	116 (4)	N1—C2—H2	125.5 (7)
C2—N1—C71	110.0 (6)	C3—C2—H2	125.5 (9)
C71—N1—H1	125.0 (7)	C5—C4—H4	120.2 (7)
C2—N1—H1	125.0 (6)	C31—C4—H4	120.2 (8)
N1—C2—C3	109.0 (6)	C4—C5—H5	118.8 (8)
C2—C3—C31	106.5 (7)	C6—C5—H5	118.9 (8)
C2—C3—C8	126.2 (6)	C6—C7—H7	121.1 (8)
C8—C3—C31	127.3 (5)	C71—C7—H7	121.0 (7)
C5—C4—C31	119.6 (7)	C3—C8—H81	108.3 (6)
C4—C5—C6	122.3 (6)	C3—C8—H82	108.2 (7)
C7—C6—C10	120.7 (7)	C9—C8—H81	108.2 (7)
C5—C6—C7	119.6 (7)	C9—C8—H82	108.2 (6)
C5—C6—C10	119.7 (6)	H81—C8—H82	109.5 (7)
C6—C7—C71	117.9 (7)	C6—C10—H101	108.6 (7)
C3—C8—C9	114.3 (5)	C6—C10—H102	108.6 (9)
O1—C9—O2	124.3 (6)	C11—C10—H101	108.4 (9)
O1—C9—C8	112.2 (5)	C11—C10—H102	108.5 (7)
O2—C9—C8	123.5 (6)	H101—C10—H102	109.5 (7)
C6—C10—C11	113.1 (6)	C10—C11—H111	113.4 (7)
C4—C31—C71	117.2 (7)	C10—C11—H112	104.9 (7)
C3—C31—C4	134.8 (7)	C10—C11—H113	110.0 (9)
C3—C31—C71	107.9 (5)	H111—C11—H112	109.5 (10)
N1—C71—C7	130.1 (7)	H111—C11—H113	109.4 (8)
N1—C71—C31	106.6 (7)	H112—C11—H113	109.5 (8)
C7—C71—C31	123.3 (6)

C2—N1—C71—C31	−0.6 (8)	C4—C5—C6—C7	0.2 (12)
C71—N1—C2—C3	0.4 (8)	C4—C5—C6—C10	179.4 (7)
C2—N1—C71—C7	−179.1 (7)	C7—C6—C10—C11	106.0 (7)
N1—C2—C3—C31	−0.1 (8)	C5—C6—C10—C11	−73.2 (9)
N1—C2—C3—C8	179.2 (6)	C10—C6—C7—C71	−179.2 (7)
C8—C3—C31—C71	−179.5 (7)	C5—C6—C7—C71	0.0 (11)
C2—C3—C8—C9	96.4 (8)	C6—C7—C71—N1	178.2 (7)
C8—C3—C31—C4	−0.5 (13)	C6—C7—C71—C31	0.0 (11)
C31—C3—C8—C9	−84.5 (8)	C3—C8—C9—O1	167.9 (5)
C2—C3—C31—C4	178.7 (8)	C3—C8—C9—O2	−12.7 (8)
C2—C3—C31—C71	−0.3 (8)	C4—C31—C71—N1	−178.7 (6)
C31—C4—C5—C6	−0.3 (11)	C4—C31—C71—C7	0.0 (11)
C5—C4—C31—C71	0.2 (11)	C3—C31—C71—C7	179.2 (7)
C5—C4—C31—C3	−178.8 (8)	C3—C31—C71—N1	0.6 (8)

Symmetry codes: (i) −x+1, y+1/2, −z+3/2; (ii) −x+1, −y, −z+1; (iii) x, −y−1/2, z−1/2; (iv) x, −y+1/2, z−1/2; (v) x, y−1, z; (vi) x, −y−1/2, z+1/2; (vii) x, −y+1/2, z+1/2; (viii) x, y+1, z; (ix) −x+1, y−1/2, −z+3/2; (x) −x, −y, −z.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H11···O2ⁱⁱ	1.03 (7)	1.61 (7)	2.635 (6)	170 (6)
C2—H2···O2^vi	1.08 (1)	2.16 (1)	3.236 (8)	172 (1)

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

(iaalt) indole-3-acetic acid top

Crystal data top

C₁₀H₉NO₂	F(000) = 368
M_r = 175.19	D_x = 1.383 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 25 reflections
a = 17.8100 (5) Å	θ = 6–17°
b = 5.1750 (4) Å	µ = 0.10 mm⁻¹
c = 9.5340 (4) Å	T = 103 K
β = 106.700 (6)°	Prismatic, colourless
V = 841.66 (8) Å³	0.60 × 0.45 × 0.15 mm
Z = 4

Data collection top

Enraf-Nonius CAD4 diffractometer	R_int = 0.014
Radiation source: fine-focus sealed tube	θ_max = 25°, θ_min = 2°
Graphite monochromator	h = −20→20
ω/2θ scans	k = 0→6
1236 measured reflections	l = 0→11
1214 independent reflections	3 standard reflections every 87 reflections
1180 reflections with I > 3σ(I)	intensity decay: 0.1%

Refinement top

Refinement on F	0 restraints
Least-squares matrix: full	0 constraints
R[F² > 2σ(F²)] = 0.038	H-atom refinement: see text
wR(F²) = 0.040	Calculated w = 5.4218/[σ²(F_o) + 0.00000(F_o²)]
S = 0.86	(Δ/σ)_max = 0.005
1180 reflections	Δρ_max = 0.20 e Å⁻³
157 parameters	Δρ_min = −0.22 e Å⁻³

Special details top

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

	x	y	z	U_iso*/U_eq
O1	0.0157 (1)	0.7342 (3)	0.3859 (2)	0.0310 (5)
O2	0.0800 (1)	1.0996 (3)	0.4669 (2)	0.0286 (5)
N1	0.2875 (1)	1.2749 (3)	0.3120 (2)	0.0281 (6)
C2	0.2129 (1)	1.1844 (4)	0.2547 (2)	0.0278 (7)
C3	0.2001 (1)	0.9785 (4)	0.3347 (2)	0.0239 (7)
C4	0.2964 (1)	0.7584 (4)	0.5629 (2)	0.0239 (6)
C5	0.3721 (1)	0.7719 (4)	0.6543 (2)	0.0272 (7)
C6	0.4241 (1)	0.9633 (4)	0.6350 (2)	0.0292 (8)
C7	0.4017 (1)	1.1432 (4)	0.5242 (2)	0.0273 (7)
C8	0.1268 (1)	0.8226 (4)	0.3066 (3)	0.0280 (7)
C9	0.0727 (1)	0.9004 (4)	0.3950 (2)	0.0239 (7)
C31	0.2716 (1)	0.9394 (4)	0.4493 (2)	0.0202 (6)
C71	0.3256 (1)	1.1285 (4)	0.4324 (2)	0.0219 (6)
H1	0.3120 (13)	1.412 (5)	0.271 (3)	0.047 (7)*
H2	0.1781 (10)	1.253 (4)	0.163 (2)	0.024 (5)*
H4	0.2591 (11)	0.623 (4)	0.579 (2)	0.030 (6)*
H5	0.3890 (11)	0.650 (4)	0.734 (2)	0.037 (6)*
H6	0.4774 (10)	0.966 (4)	0.7023 (19)	0.021 (5)*
H7	0.4395 (12)	1.274 (5)	0.508 (2)	0.045 (7)*
H11	−0.0170 (13)	0.795 (5)	0.437 (3)	0.062 (9)*
H81	0.0933 (11)	0.833 (4)	0.199 (2)	0.035 (6)*
H82	0.1394 (12)	0.651 (5)	0.330 (2)	0.041 (7)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0295 (8)	0.0248 (8)	0.0435 (10)	−0.0040 (8)	0.0183 (7)	−0.0115 (8)
O2	0.0302 (8)	0.0245 (8)	0.0338 (9)	−0.0025 (7)	0.0137 (7)	−0.0122 (8)
N1	0.0379 (11)	0.0172 (10)	0.0336 (11)	0.0031 (9)	0.0172 (9)	0.0049 (9)
C2	0.0357 (13)	0.0225 (12)	0.0264 (12)	0.0105 (10)	0.0110 (11)	−0.0004 (11)
C3	0.0284 (11)	0.0201 (11)	0.0266 (12)	0.0042 (10)	0.0133 (10)	−0.0056 (10)
C4	0.0315 (11)	0.0136 (10)	0.0326 (12)	0.0003 (10)	0.0186 (10)	−0.0011 (10)
C5	0.0341 (12)	0.0181 (11)	0.0318 (13)	0.0080 (11)	0.0133 (11)	0.0041 (11)
C6	0.0263 (12)	0.0245 (13)	0.0355 (14)	0.004 (1)	0.0068 (11)	−0.0040 (11)
C7	0.0293 (12)	0.0169 (11)	0.0404 (14)	−0.0011 (10)	0.0176 (11)	−0.0032 (11)
C8	0.0265 (12)	0.0253 (13)	0.0335 (13)	0.0026 (10)	0.0106 (11)	−0.0078 (12)
C9	0.0230 (11)	0.0231 (12)	0.0232 (11)	0.0036 (10)	0.0027 (9)	0.0005 (11)
C31	0.0272 (11)	0.0113 (10)	0.0264 (12)	0.0040 (8)	0.0146 (10)	−0.0031 (9)
C71	0.0297 (11)	0.0116 (10)	0.0289 (12)	0.0017 (9)	0.0154 (10)	−0.0006 (10)

Geometric parameters (Å, º) top

O1—C9	1.314 (3)	C6—C7	1.378 (3)
O2—C9	1.224 (3)	C7—C71	1.388 (3)
O1—H11	0.92 (3)	C8—C9	1.506 (3)
N1—C2	1.366 (3)	C31—C71	1.413 (3)
N1—C71	1.380 (3)	C2—H2	0.981 (19)
N1—H1	0.97 (3)	C4—H4	1.01 (2)
C2—C3	1.367 (3)	C5—H5	0.967 (19)
C3—C31	1.434 (3)	C6—H6	0.981 (18)
C3—C8	1.492 (3)	C7—H7	1.00 (2)
C4—C31	1.404 (3)	C8—H81	1.029 (19)
C4—C5	1.381 (3)	C8—H82	0.93 (3)
C5—C6	1.404 (3)

O1···C8ⁱ	3.416 (3)	C4···H82	3.08 (2)
O1···C9ⁱ	3.196 (3)	C4···H1ⁱⁱⁱ	2.57 (3)
O1···O2ⁱⁱ	2.644 (3)	C5···H6^x	3.075 (19)
O2···C9ⁱⁱ	3.345 (3)	C5···H1ⁱⁱⁱ	2.40 (3)
O2···O1ⁱⁱ	2.644 (3)	C6···H1ⁱⁱⁱ	2.75 (3)
O2···C2ⁱⁱⁱ	3.263 (3)	C9···H81^viii	3.063 (19)
O1···H81ⁱ	2.80 (2)	C9···H11ⁱⁱ	2.64 (3)
O2···H11ⁱⁱ	1.73 (3)	C31···H1ⁱⁱⁱ	3.04 (3)
O2···H2ⁱⁱⁱ	2.292 (19)	C71···H5^vi	2.86 (2)
N1···C4^iv	3.434 (3)	H1···C4^v	2.57 (3)
N1···C4^v	3.423 (3)	H1···C5^v	2.40 (3)
N1···C5^v	3.366 (3)	H1···C6^v	2.75 (3)
C2···O2^v	3.263 (3)	H1···C31^v	3.04 (3)
C2···C4^vi	3.517 (3)	H2···O2^v	2.292 (19)
C4···C71^vii	3.580 (3)	H4···C2^viii	2.61 (2)
C4···C2^viii	3.517 (3)	H4···C3^viii	2.966 (19)
C4···N1^vii	3.434 (3)	H5···H6^x	2.47 (3)
C4···N1ⁱⁱⁱ	3.423 (3)	H5···C71^viii	2.86 (2)
C5···C7^vii	3.575 (3)	H6···C5^xi	3.075 (19)
C5···N1ⁱⁱⁱ	3.366 (3)	H6···H5^xi	2.47 (3)
C7···C5^iv	3.575 (3)	H11···O2ⁱⁱ	1.73 (3)
C8···O1^ix	3.416 (3)	H11···C9ⁱⁱ	2.64 (3)
C9···O2ⁱⁱ	3.345 (3)	H11···H11ⁱⁱ	2.43 (4)
C9···O1^ix	3.196 (3)	H81···O1^ix	2.80 (2)
C71···C4^iv	3.580 (3)	H81···C9^vi	3.063 (19)
C2···H82^iv	2.93 (2)	H82···C2^vii	2.93 (2)
C2···H4^vi	2.61 (2)	H82···C4	3.08 (2)
C3···H4^vi	2.966 (19)

C9—O1—H11	109.7 (16)	N1—C71—C7	130.69 (19)
C2—N1—C71	109.49 (16)	N1—C71—C31	106.67 (16)
C2—N1—H1	125.9 (16)	C7—C71—C31	122.62 (18)
C71—N1—H1	124.4 (15)	N1—C2—H2	121.7 (12)
N1—C2—C3	110.06 (17)	C3—C2—H2	128.0 (12)
C2—C3—C8	126.79 (18)	C5—C4—H4	120.4 (11)
C2—C3—C31	106.33 (17)	C31—C4—H4	120.4 (11)
C8—C3—C31	126.88 (19)	C4—C5—H5	119.3 (12)
C5—C4—C31	119.13 (18)	C6—C5—H5	119.7 (12)
C4—C5—C6	120.95 (18)	C5—C6—H6	118.4 (12)
C5—C6—C7	121.37 (17)	C7—C6—H6	120.3 (12)
C6—C7—C71	117.47 (18)	C6—C7—H7	121.2 (12)
C3—C8—C9	114.99 (19)	C71—C7—H7	121.3 (12)
O1—C9—O2	122.95 (19)	C3—C8—H81	112.2 (12)
O1—C9—C8	113.23 (18)	C3—C8—H82	109.6 (14)
O2—C9—C8	123.82 (19)	C9—C8—H81	105.2 (11)
C4—C31—C71	118.45 (17)	C9—C8—H82	105.7 (13)
C3—C31—C4	134.07 (18)	H81—C8—H82	108.7 (17)
C3—C31—C71	107.44 (17)

C71—N1—C2—C3	−0.1 (2)	C5—C4—C31—C71	0.4 (3)
C2—N1—C71—C31	0.0 (2)	C31—C4—C5—C6	0.0 (3)
C2—N1—C71—C7	178.7 (2)	C4—C5—C6—C7	−0.3 (3)
N1—C2—C3—C31	0.1 (2)	C5—C6—C7—C71	0.1 (3)
N1—C2—C3—C8	−178.89 (19)	C6—C7—C71—C31	0.3 (3)
C31—C3—C8—C9	84.4 (3)	C6—C7—C71—N1	−178.3 (2)
C2—C3—C8—C9	−96.9 (3)	C3—C8—C9—O2	11.5 (3)
C2—C3—C31—C71	−0.1 (2)	C3—C8—C9—O1	−169.35 (18)
C8—C3—C31—C4	1.0 (4)	C4—C31—C71—C7	−0.5 (3)
C2—C3—C31—C4	−178.0 (2)	C3—C31—C71—N1	0.0 (2)
C8—C3—C31—C71	178.91 (19)	C4—C31—C71—N1	178.33 (17)
C5—C4—C31—C3	178.1 (2)	C3—C31—C71—C7	−178.82 (18)

Symmetry codes: (i) −x, y−1/2, −z+1/2; (ii) −x, −y+2, −z+1; (iii) x, −y+5/2, z+1/2; (iv) x, y+1, z; (v) x, −y+5/2, z−1/2; (vi) x, −y+3/2, z−1/2; (vii) x, y−1, z; (viii) x, −y+3/2, z+1/2; (ix) −x, y+1/2, −z+1/2; (x) −x+1, y−1/2, −z+3/2; (xi) −x+1, y+1/2, −z+3/2.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H11···O2ⁱⁱ	0.92 (3)	1.73 (3)	2.644 (3)	178 (2)
C2—H2···O2^v	0.98 (2)	2.29 (2)	3.263 (3)	170 (2)

Symmetry codes: (ii) −x, −y+2, −z+1; (v) x, −y+5/2, z−1/2.

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