Experimental and theoretical electron-density study of three isoindole derivatives: topological and Hirshfeld surface analysis of weak intermolecular interactions

Chęcińska, L.; Grabowsky, S.; Małecka, M.; Rybarczyk-Pirek, A.J.; Jóźwiak, A.; Paulmann, C.; Luger, P.

doi:10.1107/S0108768111041747

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Experimental and theoretical electron-density study of three isoindole derivatives: topological and Hirshfeld surface analysis of weak intermolecular interactions

L. Chęcińska, S. Grabowsky, M. Małecka, A. J. Rybarczyk-Pirek, A. Jóźwiak, C. Paulmann and P. Luger

A combined experimental and theoretical study of three isoindole derivatives was made on the basis of a topological analysis of their electron-density distributions. Experimental electron densities were determined from high-resolution X-ray diffraction data sets measured with synchrotron radiation at 100 K, whereas theoretical calculations were performed using DFT methods at the B3LYP\6-311++G(3df,3pd) level of approximation. Both experimental and theoretical models are in good agreement with each other. Since the analysed structures possess a variety of hydrogen-bonding interactions, weak intermolecular contacts of C—H

C(π), C,N(π)

C,N(π) and H

H types were subject to our special interest and are discussed in detail. They were characterized quantitatively and qualitatively by topological properties using Bader's Atoms in Molecules theory and by mapping the electron-density distribution, electrostatic potential and a geometric function on the Hirshfeld surface. This way the forces and directions of intermolecular interactions as present on the molecular surfaces were depicted and described. These interactions not only guide crystal packing, but are likewise important for recognition processes involving (aza)isoindole fragments in a biological environment.

Keywords: electron density; isoindole derivatives; weak interactions; π

π interactions; CH

π interactions; close H

H contacts.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S0108768111041747/sn5107sup1.cif Contains datablocks global, I, II, III
	Structure factor file (CIF format) https://doi.org/10.1107/S0108768111041747/sn5107Isup2.hkl Contains datablock I
	Structure factor file (CIF format) https://doi.org/10.1107/S0108768111041747/sn5107IIsup3.hkl Contains datablock II
	Structure factor file (CIF format) https://doi.org/10.1107/S0108768111041747/sn5107IIIsup4.hkl Contains datablock III
	Text file https://doi.org/10.1107/S0108768111041747/sn5107sup5.txt Extra CIF
	Portable Document Format (PDF) file https://doi.org/10.1107/S0108768111041747/sn5107sup6.pdf Electron density plots

CCDC references: 861011; 861012; 861013

Computing details top

For all compounds, data collection: MarCCD (Paulmann & Morgenroth, 2006); cell refinement: XDS (Kabsch, 1993; 2010); data reduction: XDS (Kabsch, 1993; 2010); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008). Program(s) used to refine structure: Volkov et al., (2006) for (I), (III); Volkov et al. (2006) for (II). Molecular graphics: Volkov et al., (2006) for (I), (III). Software used to prepare material for publication: Volkov et al., (2006) for (I), (III).

Figures top

(I) 3-hydroxy-2-phenyl-2,3-dihydro-isoindol-1-one top

Crystal data top

C₁₄H₁₁NO₂	Z = 8
M_r = 225.24	F(000) = 944
Orthorhombic, Pbca	D_x = 1.367 Mg m⁻³
Hall symbol: -P 2ac 2ab	Synchrotron radiation, λ = 0.60000 (2) Å
a = 11.827 (2) Å	µ = 0.09 mm⁻¹
b = 7.875 (2) Å	T = 100 K
c = 23.504 (5) Å	Plate, colourless
V = 2189.1 (8) Å³	0.5 × 0.3 × 0.15 mm

Data collection top

Huber diffractometer	13824 reflections with I > 2σ(I)
Radiation source: synchrotron	R_int = 0.000
Graphite monochromator	θ_max = 47.0°, θ_min = 1.5°
ϕ scan	h = 0→28
171219 measured reflections	k = 0→18
15560 independent reflections	l = 0→55

Refinement top

Refinement on F²	0 restraints
Least-squares matrix: full	H-atom parameters not refined
R[F² > 2σ(F²)] = 0.024	w2 = 1/[s²(F_o²)]
wR(F²) = 0.041	(Δ/σ)_max < 0.001
S = 3.18	Δρ_max = 0.25 e Å⁻³
13700 reflections	Δρ_min = −0.24 e Å⁻³
383 parameters

Crystal data top

C₁₄H₁₁NO₂	V = 2189.1 (8) Å³
M_r = 225.24	Z = 8
Orthorhombic, Pbca	Synchrotron radiation, λ = 0.60000 (2) Å
a = 11.827 (2) Å	µ = 0.09 mm⁻¹
b = 7.875 (2) Å	T = 100 K
c = 23.504 (5) Å	0.5 × 0.3 × 0.15 mm

Data collection top

Huber diffractometer	13824 reflections with I > 2σ(I)
171219 measured reflections	R_int = 0.000
15560 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.024	0 restraints
wR(F²) = 0.041	H-atom parameters not refined
S = 3.18	Δρ_max = 0.25 e Å⁻³
13700 reflections	Δρ_min = −0.24 e Å⁻³
383 parameters

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

	x	y	z	U_iso*/U_eq
O(1)	0.307099 (14)	0.01473 (2)	0.086663 (9)	0.021
O(2)	−0.004840 (13)	0.33819 (2)	0.102862 (5)	0.015
N(1)	0.125951 (11)	0.106857 (17)	0.108827 (6)	0.013
C(1)	0.214809 (12)	0.074247 (19)	0.072915 (7)	0.014
C(2)	0.177826 (12)	0.125055 (19)	0.014940 (6)	0.013
C(3)	0.236867 (12)	0.11878 (2)	−0.036447 (6)	0.016
C(4)	0.182883 (14)	0.18495 (2)	−0.084721 (6)	0.018
C(5)	0.073101 (14)	0.25231 (2)	−0.080994 (6)	0.017
C(6)	0.014171 (13)	0.25491 (2)	−0.029283 (6)	0.016
C(7)	0.068655 (12)	0.190511 (18)	0.018580 (6)	0.013
C(8)	0.026958 (11)	0.18158 (2)	0.079445 (6)	0.012
C(91)	0.128559 (11)	0.080273 (19)	0.168772 (6)	0.013
C(92)	0.222600 (13)	0.13207 (2)	0.200546 (7)	0.018
C(93)	0.225166 (16)	0.10099 (3)	0.259138 (8)	0.021
C(94)	0.134548 (17)	0.02008 (2)	0.286084 (8)	0.020
C(95)	0.039622 (16)	−0.02740 (2)	0.254439 (7)	0.020
C(96)	0.036475 (13)	0.00292 (2)	0.195825 (7)	0.017
H(2)	0.058224	0.414805	0.097506	0.026
H(3)	0.321295	0.065438	−0.038284	0.035
H(4)	0.225758	0.183698	−0.125475	0.035
H(5)	0.032486	0.302352	−0.118797	0.035
H(6)	−0.071178	0.304328	−0.026005	0.033
H(8)	−0.046993	0.097654	0.083221	0.026
H(92)	0.291301	0.194015	0.178134	0.033
H(93)	0.298086	0.139081	0.28408	0.041
H(94)	0.137051	−0.008648	0.331154	0.041
H(95)	−0.03206	−0.08639	0.275403	0.038
H(96)	−0.034794	−0.034782	0.169644	0.031

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O(1)	0.01434 (5)	0.02723 (10)	0.02169 (7)	0.00853 (5)	0.00033 (4)	−0.00001 (4)
O(2)	0.01302 (4)	0.01384 (6)	0.01735 (4)	0.00139 (4)	0.00314 (3)	−0.00176 (4)
N(1)	0.01176 (4)	0.01477 (6)	0.01290 (4)	0.00167 (3)	0.00151 (3)	0.00113 (3)
C(1)	0.01153 (4)	0.01496 (6)	0.01495 (5)	0.00262 (4)	0.00130 (3)	−0.00050 (4)
C(2)	0.01206 (4)	0.01375 (6)	0.01345 (4)	0.00076 (3)	0.00223 (3)	−0.00141 (3)
C(3)	0.01479 (4)	0.01853 (7)	0.01515 (5)	0.00001 (4)	0.00375 (4)	−0.00368 (4)
C(4)	0.02093 (5)	0.01809 (7)	0.01354 (5)	−0.00145 (4)	0.00415 (4)	−0.00221 (4)
C(5)	0.02273 (6)	0.01558 (7)	0.01310 (4)	0.00095 (4)	0.00126 (4)	0.00024 (4)
C(6)	0.01684 (5)	0.01612 (6)	0.01407 (5)	0.00289 (4)	0.00045 (4)	0.00088 (4)
C(7)	0.01219 (4)	0.01255 (6)	0.01281 (4)	0.00083 (3)	0.00142 (3)	0.00003 (3)
C(8)	0.01069 (4)	0.01242 (6)	0.01374 (4)	0.00014 (4)	0.00181 (3)	0.00030 (4)
C(91)	0.01352 (4)	0.01350 (6)	0.01326 (4)	−0.00028 (4)	0.00078 (3)	0.00078 (3)
C(92)	0.01617 (5)	0.02236 (8)	0.01618 (5)	−0.00311 (4)	−0.00125 (4)	0.00101 (4)
C(93)	0.02010 (6)	0.02802 (9)	0.01601 (5)	0.00016 (5)	−0.00318 (4)	−0.00000 (5)
C(94)	0.02375 (7)	0.02359 (9)	0.01365 (5)	0.00359 (6)	0.00063 (5)	0.00173 (4)
C(95)	0.02241 (6)	0.02316 (8)	0.01506 (5)	−0.00227 (5)	0.00411 (4)	0.00218 (4)
C(96)	0.01685 (5)	0.02087 (7)	0.01449 (5)	−0.00391 (4)	0.00241 (4)	0.00023 (4)
H(2)	0.026493	0.021706	0.030261	−0.001897	0.005811	−0.00205
H(3)	0.024146	0.046528	0.032876	0.009993	0.006908	−0.001649
H(4)	0.039434	0.04325	0.021796	0.001332	0.010675	−0.000442
H(5)	0.041711	0.040647	0.022673	0.006458	−0.003513	0.006051
H(6)	0.024935	0.04223	0.031625	0.011425	−0.000055	0.002483
H(8)	0.019427	0.028229	0.030115	−0.006249	0.001932	0.000226
H(92)	0.023377	0.048218	0.028684	−0.008282	0.002312	0.002185
H(93)	0.032291	0.060789	0.02857	−0.006478	−0.009372	0.000114
H(94)	0.049676	0.051905	0.020109	−0.004388	−0.001715	0.007334
H(95)	0.040234	0.044428	0.029108	−0.013864	0.007702	0.006341
H(96)	0.027826	0.038786	0.027428	−0.010276	−0.001962	0.000496

Geometric parameters (Å, º) top

O(1)—C(1)	1.2311 (4)	C(6)—H(6)	1.0846
O(2)—C(8)	1.4019 (4)	C(7)—C(8)	1.5148 (4)
O(2)—H(2)	0.9676	C(8)—H(8)	1.0999
N(1)—C(1)	1.3722 (4)	C(91)—C(92)	1.4004 (4)
N(1)—C(91)	1.4247 (4)	C(91)—C(96)	1.4005 (4)
C(1)—C(2)	1.4860 (4)	C(92)—C(93)	1.3991 (4)
C(2)—C(3)	1.3960 (4)	C(92)—H(92)	1.0843
C(2)—C(7)	1.3929 (4)	C(93)—C(94)	1.3985 (4)
C(3)—C(4)	1.4023 (4)	C(93)—H(93)	1.0851
C(3)—H(3)	1.0842	C(94)—C(95)	1.3977 (4)
C(4)—C(5)	1.4053 (4)	C(94)—H(94)	1.0836
C(4)—H(4)	1.0839	C(95)—C(96)	1.3987 (4)
C(5)—C(6)	1.4012 (4)	C(95)—H(95)	1.0851
C(5)—H(5)	1.0842	C(96)—H(96)	1.0850
C(6)—C(7)	1.3921 (4)

C(8)—O(2)—H(2)	106.899	C(6)—C(7)—C(8)	129.004 (13)
C(1)—N(1)—C(91)	124.349 (14)	O(2)—C(8)—C(7)	114.662 (13)
O(1)—C(1)—N(1)	126.076 (18)	O(2)—C(8)—H(8)	106.479
O(1)—C(1)—C(2)	127.170 (16)	C(7)—C(8)—H(8)	111.283
N(1)—C(1)—C(2)	106.753 (13)	N(1)—C(91)—C(92)	120.117 (13)
C(1)—C(2)—C(3)	129.539 (14)	N(1)—C(91)—C(96)	119.739 (13)
C(1)—C(2)—C(7)	108.431 (12)	C(92)—C(91)—C(96)	120.143 (15)
C(3)—C(2)—C(7)	121.999 (14)	C(91)—C(92)—C(93)	119.420 (16)
C(2)—C(3)—C(4)	117.331 (14)	C(91)—C(92)—H(92)	117.847
C(2)—C(3)—H(3)	120.588	C(93)—C(92)—H(92)	122.729
C(4)—C(3)—H(3)	122.079	C(92)—C(93)—C(94)	120.588 (17)
C(3)—C(4)—C(5)	120.695 (12)	C(92)—C(93)—H(93)	120.046
C(3)—C(4)—H(4)	119.912	C(94)—C(93)—H(93)	119.365
C(5)—C(4)—H(4)	119.391	C(93)—C(94)—C(95)	119.767 (17)
C(4)—C(5)—C(6)	121.274 (14)	C(93)—C(94)—H(94)	121.126
C(4)—C(5)—H(5)	119.700	C(95)—C(94)—H(94)	119.099
C(6)—C(5)—H(5)	119.023	C(94)—C(95)—C(96)	119.991 (17)
C(5)—C(6)—C(7)	117.736 (14)	C(94)—C(95)—H(95)	120.032
C(5)—C(6)—H(6)	121.991	C(96)—C(95)—H(95)	119.972
C(7)—C(6)—H(6)	120.273	C(91)—C(96)—C(95)	120.049 (15)
C(2)—C(7)—C(6)	120.948 (13)	C(91)—C(96)—H(96)	117.751
C(2)—C(7)—C(8)	110.036 (13)	C(95)—C(96)—H(96)	122.179

(II) 5-hydroxy-6-phenyl-5,6-dihydro-pyrrolo[3,4-b]pyridin-7-one top

Crystal data top

C₁₃H₁₀N₂O₂	Z = 4
M_r = 226.23	F(000) = 472
Monoclinic, P2₁/c	D_x = 1.430 Mg m⁻³
Hall symbol: -P 2ybc	Synchrotron radiation, λ = 0.5000 (2) Å
a = 13.659 (3) Å	µ = 0.06 mm⁻¹
b = 6.256 (1) Å	T = 100 K
c = 12.862 (3) Å	Prism, colourless
β = 107.00 (3)°	0.5 × 0.4 × 0.35 mm
V = 1051.0 (4) Å³

Data collection top

Huber diffractometer	14209 reflections with I > 2σ(I)
Radiation source: synchrotron	R_int = 0.031
Graphite monochromator	θ_max = 37.6°, θ_min = 2.2°
ϕ scan	h = −33→33
196425 measured reflections	k = −9→15
15875 independent reflections	l = −31→31

Refinement top

Refinement on F²	0 restraints
Least-squares matrix: full	H-atom parameters not refined
R[F² > 2σ(F²)] = 0.019	w2 = 1/[s²(F_o²)]
wR(F²) = 0.034	(Δ/σ)_max < 0.001
S = 2.4	Δρ_max = 0.29 e Å⁻³
14227 reflections	Δρ_min = −0.27 e Å⁻³
421 parameters

Crystal data top

C₁₃H₁₀N₂O₂	V = 1051.0 (4) Å³
M_r = 226.23	Z = 4
Monoclinic, P2₁/c	Synchrotron radiation, λ = 0.5000 (2) Å
a = 13.659 (3) Å	µ = 0.06 mm⁻¹
b = 6.256 (1) Å	T = 100 K
c = 12.862 (3) Å	0.5 × 0.4 × 0.35 mm
β = 107.00 (3)°

Data collection top

Huber diffractometer	14209 reflections with I > 2σ(I)
196425 measured reflections	R_int = 0.031
15875 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.019	0 restraints
wR(F²) = 0.034	H-atom parameters not refined
S = 2.4	Δρ_max = 0.29 e Å⁻³
14227 reflections	Δρ_min = −0.27 e Å⁻³
421 parameters

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

	x	y	z	U_iso*/U_eq
O(1)	0.282516 (9)	0.36773 (2)	0.017527 (10)	0.017
O(2)	0.124967 (10)	0.332641 (19)	0.277065 (10)	0.014
N(1)	0.260197 (8)	0.355602 (18)	0.192151 (8)	0.010
N(2)	0.153100 (9)	−0.02604 (2)	−0.018572 (9)	0.013
C(1)	0.247288 (8)	0.288259 (19)	0.086389 (9)	0.011
C(2)	0.182267 (8)	0.091165 (19)	0.072450 (8)	0.010
C(4)	0.097439 (11)	−0.20148 (2)	−0.012338 (11)	0.016
C(5)	0.070384 (11)	−0.25938 (2)	0.081278 (11)	0.017
C(6)	0.100392 (10)	−0.13090 (2)	0.174628 (10)	0.014
C(7)	0.158722 (8)	0.048730 (19)	0.168497 (9)	0.010
C(8)	0.203963 (9)	0.21978 (2)	0.251518 (9)	0.010
C(91)	0.322876 (8)	0.528488 (19)	0.245076 (9)	0.011
C(92)	0.351175 (9)	0.69374 (2)	0.184913 (10)	0.013
C(93)	0.414246 (10)	0.86043 (2)	0.239406 (13)	0.016
C(94)	0.448652 (12)	0.86632 (3)	0.353615 (14)	0.019
C(95)	0.419201 (11)	0.70305 (3)	0.412853 (12)	0.020
C(96)	0.356944 (10)	0.53436 (2)	0.359673 (10)	0.016
H(2)	0.150988	0.402459	0.346697	0.028
H(4)	0.072704	−0.289129	−0.087949	0.035
H(5)	0.028166	−0.406109	0.080214	0.033
H(6)	0.079874	−0.17375	0.247032	0.031
H(8)	0.260134	0.154822	0.324337	0.025
H(92)	0.325086	0.695381	0.096962	0.029
H(93)	0.436337	0.983675	0.191901	0.035
H(94)	0.499424	0.992492	0.39464	0.038
H(95)	0.444102	0.703817	0.500638	0.039
H(96)	0.337733	0.411296	0.409549	0.031

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O(1)	0.02461 (5)	0.01733 (4)	0.01145 (3)	−0.00774 (4)	0.01045 (3)	−0.00171 (3)
O(2)	0.01420 (4)	0.01823 (4)	0.01220 (3)	−0.00036 (3)	0.00685 (3)	−0.00367 (3)
N(1)	0.01267 (3)	0.01115 (3)	0.00826 (3)	−0.00261 (3)	0.00447 (2)	−0.00127 (2)
N(2)	0.01835 (4)	0.01306 (4)	0.00831 (3)	−0.00412 (3)	0.00536 (3)	−0.00177 (3)
C(1)	0.01375 (3)	0.01149 (4)	0.00820 (3)	−0.00224 (3)	0.00511 (2)	−0.00050 (3)
C(2)	0.01283 (3)	0.01080 (4)	0.00757 (3)	−0.00172 (3)	0.00406 (2)	−0.00057 (2)
C(4)	0.02343 (5)	0.01489 (5)	0.01108 (4)	−0.00736 (4)	0.00661 (3)	−0.00332 (3)
C(5)	0.02354 (5)	0.01519 (5)	0.01270 (4)	−0.00864 (4)	0.00730 (4)	−0.00246 (3)
C(6)	0.01890 (4)	0.01462 (4)	0.01073 (3)	−0.00600 (4)	0.00674 (3)	−0.00094 (3)
C(7)	0.01257 (3)	0.01106 (4)	0.00797 (3)	−0.00197 (3)	0.00421 (2)	−0.00042 (3)
C(8)	0.01197 (3)	0.01195 (4)	0.00769 (3)	−0.00126 (3)	0.00396 (3)	−0.00065 (3)
C(91)	0.01182 (3)	0.01146 (4)	0.01052 (3)	−0.00207 (3)	0.00452 (2)	−0.00176 (3)
C(92)	0.01350 (4)	0.01151 (4)	0.01408 (4)	−0.00187 (3)	0.00459 (3)	0.00007 (3)
C(93)	0.01646 (4)	0.01313 (4)	0.01959 (5)	−0.00426 (3)	0.00723 (4)	−0.00234 (4)
C(94)	0.02103 (5)	0.01893 (5)	0.01986 (6)	−0.00912 (5)	0.00881 (4)	−0.00773 (4)
C(95)	0.02361 (5)	0.02321 (6)	0.01419 (4)	−0.01085 (5)	0.00739 (4)	−0.00773 (4)
C(96)	0.01925 (4)	0.01841 (5)	0.01071 (3)	−0.00717 (4)	0.00586 (3)	−0.00406 (3)
H(2)	0.030054	0.034615	0.023089	−0.006346	0.012671	−0.011747
H(4)	0.050487	0.035419	0.021826	−0.017481	0.013187	−0.013098
H(5)	0.043903	0.025955	0.031381	−0.017703	0.014062	−0.003964
H(6)	0.041739	0.034585	0.020028	−0.01269	0.015708	0.000622
H(8)	0.026805	0.029166	0.015674	−0.001208	0.00203	0.003656
H(92)	0.038431	0.029403	0.019002	−0.007533	0.007757	0.000837
H(93)	0.044395	0.026881	0.035893	−0.013903	0.016093	0.00078
H(94)	0.042395	0.034898	0.037084	−0.020918	0.010411	−0.01386
H(95)	0.04829	0.047124	0.019281	−0.017948	0.006268	−0.008999
H(96)	0.03996	0.032942	0.02023	−0.012317	0.009205	0.001195

Geometric parameters (Å, º) top

O(1)—C(1)	1.2298 (4)	C(6)—H(6)	1.0818
O(2)—C(8)	1.4064 (4)	C(7)—C(8)	1.5104 (4)
O(2)—H(2)	0.9660	C(8)—H(8)	1.1004
N(1)—C(1)	1.3852 (4)	C(91)—C(92)	1.4113 (4)
N(1)—C(91)	1.4232 (4)	C(91)—C(96)	1.4104 (4)
N(2)—C(2)	1.3395 (4)	C(92)—C(93)	1.4028 (4)
N(2)—C(4)	1.3508 (4)	C(92)—H(92)	1.0822
C(1)—C(2)	1.4994 (4)	C(93)—C(94)	1.4059 (4)
C(2)—C(7)	1.3901 (4)	C(93)—H(93)	1.0801
C(4)—C(5)	1.4063 (4)	C(94)—C(95)	1.4017 (4)
C(4)—H(4)	1.0810	C(94)—H(94)	1.0810
C(5)—C(6)	1.4028 (4)	C(95)—C(96)	1.4016 (4)
C(5)—H(5)	1.0820	C(95)—H(95)	1.0798
C(6)—C(7)	1.3931 (4)	C(96)—H(96)	1.0824

C(8)—O(2)—H(2)	110.128	O(2)—C(8)—C(7)	109.73 (3)
C(1)—N(1)—C(91)	125.94 (3)	O(2)—C(8)—H(8)	112.222
C(2)—N(2)—C(4)	114.94 (3)	C(7)—C(8)—H(8)	112.302
O(1)—C(1)—N(1)	128.32 (3)	N(1)—C(91)—C(92)	121.15 (3)
O(1)—C(1)—C(2)	126.10 (3)	N(1)—C(91)—C(96)	119.22 (3)
N(1)—C(1)—C(2)	105.57 (3)	C(92)—C(91)—C(96)	119.63 (3)
N(2)—C(2)—C(1)	124.69 (3)	C(91)—C(92)—C(93)	119.82 (3)
N(2)—C(2)—C(7)	125.82 (3)	C(91)—C(92)—H(92)	121.389
C(1)—C(2)—C(7)	109.49 (3)	C(93)—C(92)—H(92)	118.795
N(2)—C(4)—C(5)	123.60 (3)	C(92)—C(93)—C(94)	120.69 (3)
N(2)—C(4)—H(4)	113.084	C(92)—C(93)—H(93)	118.707
C(5)—C(4)—H(4)	123.256	C(94)—C(93)—H(93)	120.599
C(4)—C(5)—C(6)	120.07 (3)	C(93)—C(94)—C(95)	119.17 (3)
C(4)—C(5)—H(5)	118.695	C(93)—C(94)—H(94)	120.001
C(6)—C(5)—H(5)	121.212	C(95)—C(94)—H(94)	120.788
C(5)—C(6)—C(7)	116.27 (3)	C(94)—C(95)—C(96)	120.86 (3)
C(5)—C(6)—H(6)	120.694	C(94)—C(95)—H(95)	120.822
C(7)—C(6)—H(6)	123.024	C(96)—C(95)—H(95)	118.317
C(2)—C(7)—C(6)	119.28 (3)	C(91)—C(96)—C(95)	119.82 (3)
C(2)—C(7)—C(8)	109.87 (3)	C(91)—C(96)—H(96)	122.531
C(6)—C(7)—C(8)	130.85 (3)	C(95)—C(96)—H(96)	117.640

(III) (3S)-3-hydroxy-2,3-diphenyl-2,3-dihydro-pyrrolo[3,4-c]pyridine-1-one top

Crystal data top

C₁₉H₁₄N₂O₂	Z = 4
M_r = 302.32	F(000) = 632
Orthorhombic, P2₁2₁2₁	D_x = 1.368 Mg m⁻³
Hall symbol: P 2ac 2ab	Synchrotron radiation, λ = 0.60000 (2) Å
a = 7.875 (2) Å	µ = 0.09 mm⁻¹
b = 9.892 (2) Å	T = 100 K
c = 18.843 (4) Å	Plate, colourless
V = 1467.9 (6) Å³	0.6 × 0.4 × 0.1 mm

Data collection top

Huber diffractometer	11018 reflections with I > 2σ(I)
Radiation source: synchrotron	R_int = 0.030
Graphite monochromator	θ_max = 47.0°, θ_min = 1.8°
ϕ scan	h = −10→18
144632 measured reflections	k = −23→23
11539 independent reflections	l = −44→44

Refinement top

Refinement on F²	0 restraints
Least-squares matrix: full	H-atom parameters not refined
R[F² > 2σ(F²)] = 0.018	w2 = 1/[s²(F_o²)]
wR(F²) = 0.033	(Δ/σ)_max < 0.001
S = 2.53	Δρ_max = 0.12 e Å⁻³
11025 reflections	Δρ_min = −0.20 e Å⁻³
535 parameters

Crystal data top

C₁₉H₁₄N₂O₂	V = 1467.9 (6) Å³
M_r = 302.32	Z = 4
Orthorhombic, P2₁2₁2₁	Synchrotron radiation, λ = 0.60000 (2) Å
a = 7.875 (2) Å	µ = 0.09 mm⁻¹
b = 9.892 (2) Å	T = 100 K
c = 18.843 (4) Å	0.6 × 0.4 × 0.1 mm

Data collection top

Huber diffractometer	11018 reflections with I > 2σ(I)
144632 measured reflections	R_int = 0.030
11539 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.018	0 restraints
wR(F²) = 0.033	H-atom parameters not refined
S = 2.53	Δρ_max = 0.12 e Å⁻³
11025 reflections	Δρ_min = −0.20 e Å⁻³
535 parameters

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

	x	y	z	U_iso*/U_eq
O(1)	0.28430 (3)	0.23448 (2)	0.441157 (12)	0.017
O(2)	−0.00184 (3)	0.463379 (19)	0.603124 (9)	0.014
N(1)	0.22664 (2)	0.395020 (16)	0.527885 (9)	0.012
N(2)	0.10004 (3)	0.05013 (3)	0.687217 (17)	0.020
C(1)	0.24290 (3)	0.266386 (18)	0.502214 (11)	0.013
C(2)	0.20009 (3)	0.173366 (18)	0.561845 (12)	0.013
C(3)	0.20173 (3)	0.03311 (2)	0.565727 (16)	0.018
C(4)	0.15064 (4)	−0.02299 (2)	0.630745 (19)	0.020
C(6)	0.09873 (3)	0.18592 (2)	0.681760 (14)	0.016
C(7)	0.14905 (3)	0.250339 (18)	0.619646 (11)	0.012
C(8)	0.15737 (3)	0.400503 (17)	0.602387 (10)	0.011
C(81)	0.27700 (3)	0.474790 (18)	0.652814 (10)	0.012
C(82)	0.44849 (3)	0.43640 (2)	0.657127 (12)	0.015
C(83)	0.55758 (4)	0.50247 (2)	0.704145 (12)	0.016
C(84)	0.49555 (4)	0.60677 (3)	0.747340 (13)	0.019
C(85)	0.32521 (4)	0.64389 (3)	0.743592 (14)	0.021
C(86)	0.21550 (3)	0.57779 (2)	0.696392 (12)	0.017
C(91)	0.24567 (3)	0.513497 (17)	0.484738 (10)	0.012
C(92)	0.15749 (3)	0.52214 (2)	0.420407 (11)	0.017
C(93)	0.17564 (4)	0.63678 (2)	0.377554 (13)	0.021
C(94)	0.28136 (4)	0.74292 (2)	0.398930 (14)	0.019
C(95)	0.36954 (3)	0.733659 (19)	0.463093 (13)	0.017
C(96)	0.35230 (3)	0.619317 (18)	0.506223 (11)	0.015
H(2)	−0.082001	0.397551	0.585319	0.024
H(3)	0.23662	−0.032576	0.522153	0.035
H(4)	0.16026	−0.1315	0.636842	0.038
H(6)	0.063662	0.243231	0.728586	0.032
H(82)	0.493906	0.355429	0.623531	0.028
H(83)	0.688052	0.467998	0.705608	0.033
H(84)	0.581197	0.659505	0.782595	0.038
H(85)	0.275451	0.720103	0.779097	0.037
H(86)	0.081781	0.60284	0.69188	0.031
H(92)	0.07034	0.443057	0.404427	0.031
H(93)	0.112656	0.639423	0.326587	0.039
H(94)	0.295779	0.83207	0.366242	0.040
H(95)	0.454773	0.81503	0.477276	0.034
H(96)	0.419992	0.612977	0.55613	0.027

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O(1)	0.02031 (10)	0.01420 (6)	0.01680 (6)	0.00129 (5)	0.00447 (6)	−0.00429 (5)
O(2)	0.01139 (7)	0.01231 (5)	0.01754 (6)	0.00163 (5)	−0.00121 (4)	−0.00281 (4)
N(1)	0.01472 (7)	0.00878 (4)	0.01239 (5)	−0.00034 (4)	0.00089 (4)	−0.00097 (4)
N(2)	0.01944 (11)	0.01690 (7)	0.02303 (9)	−0.00266 (5)	−0.00141 (7)	0.00765 (7)
C(1)	0.01313 (8)	0.00976 (5)	0.01464 (6)	0.00026 (4)	0.00166 (5)	−0.00212 (4)
C(2)	0.01304 (8)	0.00899 (5)	0.01752 (7)	0.00031 (4)	0.00060 (5)	−0.00032 (5)
C(3)	0.01851 (10)	0.00936 (5)	0.02566 (9)	0.00051 (5)	0.00012 (7)	−0.00008 (6)
C(4)	0.02034 (12)	0.01190 (6)	0.02879 (11)	−0.00149 (6)	−0.00230 (8)	0.00544 (7)
C(6)	0.01600 (9)	0.01646 (7)	0.01649 (7)	−0.00138 (5)	0.00018 (6)	0.00412 (6)
C(7)	0.01188 (7)	0.01053 (5)	0.01437 (6)	−0.00017 (4)	−0.00001 (5)	0.00093 (4)
C(8)	0.01131 (7)	0.00979 (4)	0.01264 (5)	0.00038 (4)	−0.00012 (5)	−0.00104 (4)
C(81)	0.01149 (7)	0.01177 (5)	0.01270 (5)	−0.00026 (5)	−0.00019 (5)	−0.00162 (4)
C(82)	0.01258 (8)	0.01444 (5)	0.01687 (6)	0.00118 (5)	−0.00195 (6)	−0.00150 (5)
C(83)	0.01342 (9)	0.01677 (6)	0.01842 (7)	−0.00150 (6)	−0.00323 (6)	0.00050 (6)
C(84)	0.01667 (10)	0.02032 (7)	0.01916 (7)	−0.00418 (7)	−0.00306 (7)	−0.00410 (7)
C(85)	0.01713 (11)	0.02311 (8)	0.02334 (9)	−0.00199 (7)	−0.00110 (7)	−0.01171 (7)
C(86)	0.01342 (8)	0.01819 (6)	0.01915 (7)	−0.00050 (5)	0.00016 (6)	−0.00800 (6)
C(91)	0.01322 (7)	0.01003 (4)	0.01312 (5)	−0.00083 (4)	−0.00015 (5)	−0.00025 (4)
C(92)	0.01961 (10)	0.01514 (6)	0.01595 (6)	−0.00359 (6)	−0.00424 (6)	0.00202 (5)
C(93)	0.02556 (12)	0.01842 (7)	0.01869 (7)	−0.00348 (7)	−0.00623 (7)	0.00555 (6)
C(94)	0.02245 (11)	0.01378 (6)	0.02029 (7)	−0.00118 (6)	−0.00115 (8)	0.00467 (6)
C(95)	0.01955 (10)	0.01113 (5)	0.01971 (7)	−0.00273 (5)	−0.00016 (6)	0.00119 (5)
C(96)	0.01750 (8)	0.01127 (5)	0.01610 (6)	−0.00307 (5)	−0.00187 (6)	0.00034 (4)
H(2)	0.019866	0.02117	0.031984	−0.00186	−0.002616	−0.004974
H(3)	0.043445	0.020139	0.040007	0.002461	0.005454	−0.007153
H(4)	0.045573	0.017092	0.052525	−0.000197	−0.000106	0.008566
H(6)	0.038105	0.033458	0.024127	−0.002099	0.005359	−0.001695
H(82)	0.025342	0.025171	0.033517	0.004836	0.000021	−0.007774
H(83)	0.019802	0.037726	0.042071	0.00303	−0.006788	−0.002764
H(84)	0.032182	0.043995	0.036563	−0.006903	−0.010955	−0.013593
H(85)	0.035663	0.040727	0.03588	0.001172	0.001186	−0.021315
H(86)	0.019555	0.035237	0.037378	0.003909	−0.000523	−0.011378
H(92)	0.037024	0.025984	0.030432	−0.009949	−0.008334	0.000253
H(93)	0.05078	0.039095	0.027855	−0.008872	−0.014145	0.009439
H(94)	0.050627	0.028723	0.041259	−0.009717	−0.007967	0.017131
H(95)	0.035484	0.022804	0.042483	−0.010658	−0.006208	0.00347
H(96)	0.029853	0.026081	0.026216	−0.002842	−0.007353	0.001078

Geometric parameters (Å, º) top

O(1)—C(1)	1.2367 (3)	C(82)—H(82)	1.0817
O(2)—C(8)	1.3996 (3)	C(83)—C(84)	1.4020 (4)
O(2)—H(2)	0.9670	C(83)—H(83)	1.0829
N(1)—C(1)	1.3673 (2)	C(84)—C(85)	1.3926 (5)
N(1)—C(91)	1.4342 (3)	C(84)—H(84)	1.0809
N(2)—C(4)	1.3470 (5)	C(85)—C(86)	1.4017 (3)
N(2)—C(6)	1.3472 (4)	C(85)—H(85)	1.0814
C(1)—C(2)	1.4909 (3)	C(86)—H(86)	1.0851
C(2)—C(3)	1.3894 (3)	C(91)—C(92)	1.3996 (3)
C(2)—C(7)	1.3884 (3)	C(91)—C(96)	1.4017 (3)
C(3)—C(4)	1.4039 (4)	C(92)—C(93)	1.3994 (3)
C(3)—H(3)	1.0825	C(92)—H(92)	1.0834
C(4)—H(4)	1.0821	C(93)—C(94)	1.3992 (4)
C(6)—C(7)	1.3903 (3)	C(93)—H(93)	1.0812
C(6)—H(6)	1.0845	C(94)—C(95)	1.3973 (4)
C(7)—C(8)	1.5220 (3)	C(94)—H(94)	1.0817
C(8)—C(81)	1.5266 (3)	C(95)—C(96)	1.3994 (3)
C(81)—C(82)	1.4052 (3)	C(95)—H(95)	1.0816
C(81)—C(86)	1.3954 (3)	C(96)—H(96)	1.0828
C(82)—C(83)	1.3965 (3)

C(8)—O(2)—H(2)	106.385	C(82)—C(83)—C(84)	119.89 (3)
C(1)—N(1)—C(91)	123.376 (17)	C(82)—C(83)—H(83)	116.90
C(4)—N(2)—C(6)	118.52 (3)	C(84)—C(83)—H(83)	123.20
O(1)—C(1)—N(1)	126.25 (2)	C(83)—C(84)—C(85)	120.02 (2)
O(1)—C(1)—C(2)	127.098 (19)	C(83)—C(84)—H(84)	119.64
N(1)—C(1)—C(2)	106.652 (17)	C(85)—C(84)—H(84)	120.33
C(1)—C(2)—C(3)	130.83 (2)	C(84)—C(85)—C(86)	120.19 (2)
C(1)—C(2)—C(7)	108.555 (16)	C(84)—C(85)—H(85)	120.10
C(3)—C(2)—C(7)	120.60 (2)	C(86)—C(85)—H(85)	119.63
C(2)—C(3)—C(4)	115.98 (3)	C(81)—C(86)—C(85)	120.00 (2)
C(2)—C(3)—H(3)	124.18	C(81)—C(86)—H(86)	117.22
C(4)—C(3)—H(3)	119.83	C(85)—C(86)—H(86)	122.77
N(2)—C(4)—C(3)	124.19 (2)	N(1)—C(91)—C(92)	119.278 (18)
N(2)—C(4)—H(4)	118.00	N(1)—C(91)—C(96)	120.604 (18)
C(3)—C(4)—H(4)	117.69	C(92)—C(91)—C(96)	120.116 (18)
N(2)—C(6)—C(7)	121.27 (3)	C(91)—C(92)—C(93)	119.90 (2)
N(2)—C(6)—H(6)	117.46	C(91)—C(92)—H(92)	120.725
C(7)—C(6)—H(6)	121.19	C(93)—C(92)—H(92)	119.31
C(2)—C(7)—C(6)	119.442 (19)	C(92)—C(93)—C(94)	120.18 (2)
C(2)—C(7)—C(8)	110.803 (17)	C(92)—C(93)—H(93)	119.03
C(6)—C(7)—C(8)	129.75 (2)	C(94)—C(93)—H(93)	120.70
O(2)—C(8)—C(7)	113.142 (18)	C(93)—C(94)—C(95)	119.71 (2)
O(2)—C(8)—C(81)	109.435 (16)	C(93)—C(94)—H(94)	120.69
C(7)—C(8)—C(81)	111.307 (16)	C(95)—C(94)—H(94)	119.60
C(8)—C(81)—C(82)	119.935 (17)	C(94)—C(95)—C(96)	120.48 (2)
C(8)—C(81)—C(86)	120.24 (2)	C(94)—C(95)—H(95)	118.26
C(82)—C(81)—C(86)	119.79 (2)	C(96)—C(95)—H(95)	121.21
C(81)—C(82)—C(83)	120.09 (2)	C(91)—C(96)—C(95)	119.60 (2)
C(81)—C(82)—H(82)	118.95	C(91)—C(96)—H(96)	120.167
C(83)—C(82)—H(82)	120.96	C(95)—C(96)—H(96)	120.227

Experimental details

	(I)	(II)	(III)
Crystal data
Chemical formula	C₁₄H₁₁NO₂	C₁₃H₁₀N₂O₂	C₁₉H₁₄N₂O₂
M_r	225.24	226.23	302.32
Crystal system, space group	Orthorhombic, Pbca	Monoclinic, P2₁/c	Orthorhombic, P2₁2₁2₁
Temperature (K)	100	100	100
a, b, c (Å)	11.827 (2), 7.875 (2), 23.504 (5)	13.659 (3), 6.256 (1), 12.862 (3)	7.875 (2), 9.892 (2), 18.843 (4)
α, β, γ (°)	90, 90, 90	90, 107.00 (3), 90	90, 90, 90
V (Å³)	2189.1 (8)	1051.0 (4)	1467.9 (6)
Z	8	4	4
Radiation type	Synchrotron, λ = 0.60000 (2) Å	Synchrotron, λ = 0.5000 (2) Å	Synchrotron, λ = 0.60000 (2) Å
µ (mm⁻¹)	0.09	0.06	0.09
Crystal size (mm)	0.5 × 0.3 × 0.15	0.5 × 0.4 × 0.35	0.6 × 0.4 × 0.1

Data collection
Diffractometer	Huber diffractometer	Huber diffractometer	Huber diffractometer
Absorption correction	–	–	–
No. of measured, independent and observed [I > 2σ(I)] reflections	171219, 15560, 13824	196425, 15875, 14209	144632, 11539, 11018
R_int	0.000	0.031	0.030

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.024, 0.041, 3.18	0.019, 0.034, 2.4	0.018, 0.033, 2.53
No. of reflections	13700	14227	11025
No. of parameters	383	421	535
H-atom treatment	H-atom parameters not refined	H-atom parameters not refined	H-atom parameters not refined
Δρ_max, Δρ_min (e Å⁻³)	0.25, −0.24	0.29, −0.27	0.12, −0.20

Computer programs: MarCCD (Paulmann & Morgenroth, 2006), XDS (Kabsch, 1993; 2010), SHELXS97 (Sheldrick, 2008), Volkov et al., (2006), Volkov et al. (2006).

Selected geometric parameters (Å, º) for (I) top

O(1)—C(1)	1.2311 (4)	C(6)—H(6)	1.0846
O(2)—C(8)	1.4019 (4)	C(7)—C(8)	1.5148 (4)
O(2)—H(2)	0.9676	C(8)—H(8)	1.0999
N(1)—C(1)	1.3722 (4)	C(91)—C(92)	1.4004 (4)
N(1)—C(91)	1.4247 (4)	C(91)—C(96)	1.4005 (4)
C(1)—C(2)	1.4860 (4)	C(92)—C(93)	1.3991 (4)
C(2)—C(3)	1.3960 (4)	C(92)—H(92)	1.0843
C(2)—C(7)	1.3929 (4)	C(93)—C(94)	1.3985 (4)
C(3)—C(4)	1.4023 (4)	C(93)—H(93)	1.0851
C(3)—H(3)	1.0842	C(94)—C(95)	1.3977 (4)
C(4)—C(5)	1.4053 (4)	C(94)—H(94)	1.0836
C(4)—H(4)	1.0839	C(95)—C(96)	1.3987 (4)
C(5)—C(6)	1.4012 (4)	C(95)—H(95)	1.0851
C(5)—H(5)	1.0842	C(96)—H(96)	1.0850
C(6)—C(7)	1.3921 (4)

C(8)—O(2)—H(2)	106.899	C(6)—C(7)—C(8)	129.004 (13)
C(1)—N(1)—C(91)	124.349 (14)	O(2)—C(8)—C(7)	114.662 (13)
O(1)—C(1)—N(1)	126.076 (18)	O(2)—C(8)—H(8)	106.479
O(1)—C(1)—C(2)	127.170 (16)	C(7)—C(8)—H(8)	111.283
N(1)—C(1)—C(2)	106.753 (13)	N(1)—C(91)—C(92)	120.117 (13)
C(1)—C(2)—C(3)	129.539 (14)	N(1)—C(91)—C(96)	119.739 (13)
C(1)—C(2)—C(7)	108.431 (12)	C(92)—C(91)—C(96)	120.143 (15)
C(3)—C(2)—C(7)	121.999 (14)	C(91)—C(92)—C(93)	119.420 (16)
C(2)—C(3)—C(4)	117.331 (14)	C(91)—C(92)—H(92)	117.847
C(2)—C(3)—H(3)	120.588	C(93)—C(92)—H(92)	122.729
C(4)—C(3)—H(3)	122.079	C(92)—C(93)—C(94)	120.588 (17)
C(3)—C(4)—C(5)	120.695 (12)	C(92)—C(93)—H(93)	120.046
C(3)—C(4)—H(4)	119.912	C(94)—C(93)—H(93)	119.365
C(5)—C(4)—H(4)	119.391	C(93)—C(94)—C(95)	119.767 (17)
C(4)—C(5)—C(6)	121.274 (14)	C(93)—C(94)—H(94)	121.126
C(4)—C(5)—H(5)	119.700	C(95)—C(94)—H(94)	119.099
C(6)—C(5)—H(5)	119.023	C(94)—C(95)—C(96)	119.991 (17)
C(5)—C(6)—C(7)	117.736 (14)	C(94)—C(95)—H(95)	120.032
C(5)—C(6)—H(6)	121.991	C(96)—C(95)—H(95)	119.972
C(7)—C(6)—H(6)	120.273	C(91)—C(96)—C(95)	120.049 (15)
C(2)—C(7)—C(6)	120.948 (13)	C(91)—C(96)—H(96)	117.751
C(2)—C(7)—C(8)	110.036 (13)	C(95)—C(96)—H(96)	122.179

Selected geometric parameters (Å, º) for (II) top

O(1)—C(1)	1.2298 (4)	C(6)—H(6)	1.0818
O(2)—C(8)	1.4064 (4)	C(7)—C(8)	1.5104 (4)
O(2)—H(2)	0.9660	C(8)—H(8)	1.1004
N(1)—C(1)	1.3852 (4)	C(91)—C(92)	1.4113 (4)
N(1)—C(91)	1.4232 (4)	C(91)—C(96)	1.4104 (4)
N(2)—C(2)	1.3395 (4)	C(92)—C(93)	1.4028 (4)
N(2)—C(4)	1.3508 (4)	C(92)—H(92)	1.0822
C(1)—C(2)	1.4994 (4)	C(93)—C(94)	1.4059 (4)
C(2)—C(7)	1.3901 (4)	C(93)—H(93)	1.0801
C(4)—C(5)	1.4063 (4)	C(94)—C(95)	1.4017 (4)
C(4)—H(4)	1.0810	C(94)—H(94)	1.0810
C(5)—C(6)	1.4028 (4)	C(95)—C(96)	1.4016 (4)
C(5)—H(5)	1.0820	C(95)—H(95)	1.0798
C(6)—C(7)	1.3931 (4)	C(96)—H(96)	1.0824

C(8)—O(2)—H(2)	110.128	O(2)—C(8)—C(7)	109.73 (3)
C(1)—N(1)—C(91)	125.94 (3)	O(2)—C(8)—H(8)	112.222
C(2)—N(2)—C(4)	114.94 (3)	C(7)—C(8)—H(8)	112.302
O(1)—C(1)—N(1)	128.32 (3)	N(1)—C(91)—C(92)	121.15 (3)
O(1)—C(1)—C(2)	126.10 (3)	N(1)—C(91)—C(96)	119.22 (3)
N(1)—C(1)—C(2)	105.57 (3)	C(92)—C(91)—C(96)	119.63 (3)
N(2)—C(2)—C(1)	124.69 (3)	C(91)—C(92)—C(93)	119.82 (3)
N(2)—C(2)—C(7)	125.82 (3)	C(91)—C(92)—H(92)	121.389
C(1)—C(2)—C(7)	109.49 (3)	C(93)—C(92)—H(92)	118.795
N(2)—C(4)—C(5)	123.60 (3)	C(92)—C(93)—C(94)	120.69 (3)
N(2)—C(4)—H(4)	113.084	C(92)—C(93)—H(93)	118.707
C(5)—C(4)—H(4)	123.256	C(94)—C(93)—H(93)	120.599
C(4)—C(5)—C(6)	120.07 (3)	C(93)—C(94)—C(95)	119.17 (3)
C(4)—C(5)—H(5)	118.695	C(93)—C(94)—H(94)	120.001
C(6)—C(5)—H(5)	121.212	C(95)—C(94)—H(94)	120.788
C(5)—C(6)—C(7)	116.27 (3)	C(94)—C(95)—C(96)	120.86 (3)
C(5)—C(6)—H(6)	120.694	C(94)—C(95)—H(95)	120.822
C(7)—C(6)—H(6)	123.024	C(96)—C(95)—H(95)	118.317
C(2)—C(7)—C(6)	119.28 (3)	C(91)—C(96)—C(95)	119.82 (3)
C(2)—C(7)—C(8)	109.87 (3)	C(91)—C(96)—H(96)	122.531
C(6)—C(7)—C(8)	130.85 (3)	C(95)—C(96)—H(96)	117.640

Selected geometric parameters (Å, º) for (III) top

O(1)—C(1)	1.2367 (3)	C(82)—H(82)	1.0817
O(2)—C(8)	1.3996 (3)	C(83)—C(84)	1.4020 (4)
O(2)—H(2)	0.9670	C(83)—H(83)	1.0829
N(1)—C(1)	1.3673 (2)	C(84)—C(85)	1.3926 (5)
N(1)—C(91)	1.4342 (3)	C(84)—H(84)	1.0809
N(2)—C(4)	1.3470 (5)	C(85)—C(86)	1.4017 (3)
N(2)—C(6)	1.3472 (4)	C(85)—H(85)	1.0814
C(1)—C(2)	1.4909 (3)	C(86)—H(86)	1.0851
C(2)—C(3)	1.3894 (3)	C(91)—C(92)	1.3996 (3)
C(2)—C(7)	1.3884 (3)	C(91)—C(96)	1.4017 (3)
C(3)—C(4)	1.4039 (4)	C(92)—C(93)	1.3994 (3)
C(3)—H(3)	1.0825	C(92)—H(92)	1.0834
C(4)—H(4)	1.0821	C(93)—C(94)	1.3992 (4)
C(6)—C(7)	1.3903 (3)	C(93)—H(93)	1.0812
C(6)—H(6)	1.0845	C(94)—C(95)	1.3973 (4)
C(7)—C(8)	1.5220 (3)	C(94)—H(94)	1.0817
C(8)—C(81)	1.5266 (3)	C(95)—C(96)	1.3994 (3)
C(81)—C(82)	1.4052 (3)	C(95)—H(95)	1.0816
C(81)—C(86)	1.3954 (3)	C(96)—H(96)	1.0828
C(82)—C(83)	1.3965 (3)

C(8)—O(2)—H(2)	106.385	C(82)—C(83)—C(84)	119.89 (3)
C(1)—N(1)—C(91)	123.376 (17)	C(82)—C(83)—H(83)	116.90
C(4)—N(2)—C(6)	118.52 (3)	C(84)—C(83)—H(83)	123.20
O(1)—C(1)—N(1)	126.25 (2)	C(83)—C(84)—C(85)	120.02 (2)
O(1)—C(1)—C(2)	127.098 (19)	C(83)—C(84)—H(84)	119.64
N(1)—C(1)—C(2)	106.652 (17)	C(85)—C(84)—H(84)	120.33
C(1)—C(2)—C(3)	130.83 (2)	C(84)—C(85)—C(86)	120.19 (2)
C(1)—C(2)—C(7)	108.555 (16)	C(84)—C(85)—H(85)	120.10
C(3)—C(2)—C(7)	120.60 (2)	C(86)—C(85)—H(85)	119.63
C(2)—C(3)—C(4)	115.98 (3)	C(81)—C(86)—C(85)	120.00 (2)
C(2)—C(3)—H(3)	124.18	C(81)—C(86)—H(86)	117.22
C(4)—C(3)—H(3)	119.83	C(85)—C(86)—H(86)	122.77
N(2)—C(4)—C(3)	124.19 (2)	N(1)—C(91)—C(92)	119.278 (18)
N(2)—C(4)—H(4)	118.00	N(1)—C(91)—C(96)	120.604 (18)
C(3)—C(4)—H(4)	117.69	C(92)—C(91)—C(96)	120.116 (18)
N(2)—C(6)—C(7)	121.27 (3)	C(91)—C(92)—C(93)	119.90 (2)
N(2)—C(6)—H(6)	117.46	C(91)—C(92)—H(92)	120.725
C(7)—C(6)—H(6)	121.19	C(93)—C(92)—H(92)	119.31
C(2)—C(7)—C(6)	119.442 (19)	C(92)—C(93)—C(94)	120.18 (2)
C(2)—C(7)—C(8)	110.803 (17)	C(92)—C(93)—H(93)	119.03
C(6)—C(7)—C(8)	129.75 (2)	C(94)—C(93)—H(93)	120.70
O(2)—C(8)—C(7)	113.142 (18)	C(93)—C(94)—C(95)	119.71 (2)
O(2)—C(8)—C(81)	109.435 (16)	C(93)—C(94)—H(94)	120.69
C(7)—C(8)—C(81)	111.307 (16)	C(95)—C(94)—H(94)	119.60
C(8)—C(81)—C(82)	119.935 (17)	C(94)—C(95)—C(96)	120.48 (2)
C(8)—C(81)—C(86)	120.24 (2)	C(94)—C(95)—H(95)	118.26
C(82)—C(81)—C(86)	119.79 (2)	C(96)—C(95)—H(95)	121.21
C(81)—C(82)—C(83)	120.09 (2)	C(91)—C(96)—C(95)	119.60 (2)
C(81)—C(82)—H(82)	118.95	C(91)—C(96)—H(96)	120.167
C(83)—C(82)—H(82)	120.96	C(95)—C(96)—H(96)	120.227

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