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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.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S0108768111041747/sn5107sup1.cif
Contains datablocks global, I, II, III

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108768111041747/sn5107Isup2.hkl
Contains datablock I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108768111041747/sn5107IIsup3.hkl
Contains datablock II

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108768111041747/sn5107IIIsup4.hkl
Contains datablock III

txt

Text file https://doi.org/10.1107/S0108768111041747/sn5107sup5.txt
Extra CIF

pdf

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
[Figure 1]
[Figure 2]
[Figure 3]
[Figure 4]
[Figure 5]
[Figure 6]
(I) 3-hydroxy-2-phenyl-2,3-dihydro-isoindol-1-one top
Crystal data top
C14H11NO2Z = 8
Mr = 225.24F(000) = 944
Orthorhombic, PbcaDx = 1.367 Mg m3
Hall symbol: -P 2ac 2abSynchrotron radiation, λ = 0.60000 (2) Å
a = 11.827 (2) ŵ = 0.09 mm1
b = 7.875 (2) ÅT = 100 K
c = 23.504 (5) ÅPlate, colourless
V = 2189.1 (8) Å30.5 × 0.3 × 0.15 mm
Data collection top
Huber
diffractometer
13824 reflections with I > 2σ(I)
Radiation source: synchrotronRint = 0.000
Graphite monochromatorθmax = 47.0°, θmin = 1.5°
ϕ scanh = 028
171219 measured reflectionsk = 018
15560 independent reflectionsl = 055
Refinement top
Refinement on F20 restraints
Least-squares matrix: fullH-atom parameters not refined
R[F2 > 2σ(F2)] = 0.024 w2 = 1/[s2(Fo2)]
wR(F2) = 0.041(Δ/σ)max < 0.001
S = 3.18Δρmax = 0.25 e Å3
13700 reflectionsΔρmin = 0.24 e Å3
383 parameters
Crystal data top
C14H11NO2V = 2189.1 (8) Å3
Mr = 225.24Z = 8
Orthorhombic, PbcaSynchrotron radiation, λ = 0.60000 (2) Å
a = 11.827 (2) ŵ = 0.09 mm1
b = 7.875 (2) ÅT = 100 K
c = 23.504 (5) Å0.5 × 0.3 × 0.15 mm
Data collection top
Huber
diffractometer
13824 reflections with I > 2σ(I)
171219 measured reflectionsRint = 0.000
15560 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0240 restraints
wR(F2) = 0.041H-atom parameters not refined
S = 3.18Δρmax = 0.25 e Å3
13700 reflectionsΔρmin = 0.24 e Å3
383 parameters
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
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)0.0582240.4148050.0975060.026
H(3)0.3212950.0654380.0382840.035
H(4)0.2257580.1836980.1254750.035
H(5)0.0324860.3023520.1187970.035
H(6)0.0711780.3043280.0260050.033
H(8)0.0469930.0976540.0832210.026
H(92)0.2913010.1940150.1781340.033
H(93)0.2980860.1390810.284080.041
H(94)0.1370510.0086480.3311540.041
H(95)0.032060.086390.2754030.038
H(96)0.0347940.0347820.1696440.031
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
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)0.0264930.0217060.0302610.0018970.0058110.00205
H(3)0.0241460.0465280.0328760.0099930.0069080.001649
H(4)0.0394340.043250.0217960.0013320.0106750.000442
H(5)0.0417110.0406470.0226730.0064580.0035130.006051
H(6)0.0249350.042230.0316250.0114250.0000550.002483
H(8)0.0194270.0282290.0301150.0062490.0019320.000226
H(92)0.0233770.0482180.0286840.0082820.0023120.002185
H(93)0.0322910.0607890.028570.0064780.0093720.000114
H(94)0.0496760.0519050.0201090.0043880.0017150.007334
H(95)0.0402340.0444280.0291080.0138640.0077020.006341
H(96)0.0278260.0387860.0274280.0102760.0019620.000496
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)0.9676C(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)1.0842C(94)—C(95)1.3977 (4)
C(4)—C(5)1.4053 (4)C(94)—H(94)1.0836
C(4)—H(4)1.0839C(95)—C(96)1.3987 (4)
C(5)—C(6)1.4012 (4)C(95)—H(95)1.0851
C(5)—H(5)1.0842C(96)—H(96)1.0850
C(6)—C(7)1.3921 (4)
C(8)—O(2)—H(2)106.899C(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)120.588C(93)—C(92)—H(92)122.729
C(4)—C(3)—H(3)122.079C(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)119.912C(94)—C(93)—H(93)119.365
C(5)—C(4)—H(4)119.391C(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)119.700C(95)—C(94)—H(94)119.099
C(6)—C(5)—H(5)119.023C(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)121.991C(96)—C(95)—H(95)119.972
C(7)—C(6)—H(6)120.273C(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
C13H10N2O2Z = 4
Mr = 226.23F(000) = 472
Monoclinic, P21/cDx = 1.430 Mg m3
Hall symbol: -P 2ybcSynchrotron radiation, λ = 0.5000 (2) Å
a = 13.659 (3) ŵ = 0.06 mm1
b = 6.256 (1) ÅT = 100 K
c = 12.862 (3) ÅPrism, 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: synchrotronRint = 0.031
Graphite monochromatorθmax = 37.6°, θmin = 2.2°
ϕ scanh = 3333
196425 measured reflectionsk = 915
15875 independent reflectionsl = 3131
Refinement top
Refinement on F20 restraints
Least-squares matrix: fullH-atom parameters not refined
R[F2 > 2σ(F2)] = 0.019 w2 = 1/[s2(Fo2)]
wR(F2) = 0.034(Δ/σ)max < 0.001
S = 2.4Δρmax = 0.29 e Å3
14227 reflectionsΔρmin = 0.27 e Å3
421 parameters
Crystal data top
C13H10N2O2V = 1051.0 (4) Å3
Mr = 226.23Z = 4
Monoclinic, P21/cSynchrotron radiation, λ = 0.5000 (2) Å
a = 13.659 (3) ŵ = 0.06 mm1
b = 6.256 (1) ÅT = 100 K
c = 12.862 (3) Å0.5 × 0.4 × 0.35 mm
β = 107.00 (3)°
Data collection top
Huber
diffractometer
14209 reflections with I > 2σ(I)
196425 measured reflectionsRint = 0.031
15875 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0190 restraints
wR(F2) = 0.034H-atom parameters not refined
S = 2.4Δρmax = 0.29 e Å3
14227 reflectionsΔρmin = 0.27 e Å3
421 parameters
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
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)0.1509880.4024590.3466970.028
H(4)0.0727040.2891290.0879490.035
H(5)0.0281660.4061090.0802140.033
H(6)0.0798740.173750.2470320.031
H(8)0.2601340.1548220.3243370.025
H(92)0.3250860.6953810.0969620.029
H(93)0.4363370.9836750.1919010.035
H(94)0.4994240.9924920.394640.038
H(95)0.4441020.7038170.5006380.039
H(96)0.3377330.4112960.4095490.031
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
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)0.0300540.0346150.0230890.0063460.0126710.011747
H(4)0.0504870.0354190.0218260.0174810.0131870.013098
H(5)0.0439030.0259550.0313810.0177030.0140620.003964
H(6)0.0417390.0345850.0200280.012690.0157080.000622
H(8)0.0268050.0291660.0156740.0012080.002030.003656
H(92)0.0384310.0294030.0190020.0075330.0077570.000837
H(93)0.0443950.0268810.0358930.0139030.0160930.00078
H(94)0.0423950.0348980.0370840.0209180.0104110.01386
H(95)0.048290.0471240.0192810.0179480.0062680.008999
H(96)0.039960.0329420.020230.0123170.0092050.001195
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)0.9660C(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)1.0810C(94)—H(94)1.0810
C(5)—C(6)1.4028 (4)C(95)—C(96)1.4016 (4)
C(5)—H(5)1.0820C(95)—H(95)1.0798
C(6)—C(7)1.3931 (4)C(96)—H(96)1.0824
C(8)—O(2)—H(2)110.128O(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)113.084C(92)—C(93)—H(93)118.707
C(5)—C(4)—H(4)123.256C(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)118.695C(93)—C(94)—H(94)120.001
C(6)—C(5)—H(5)121.212C(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)120.694C(94)—C(95)—H(95)120.822
C(7)—C(6)—H(6)123.024C(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
C19H14N2O2Z = 4
Mr = 302.32F(000) = 632
Orthorhombic, P212121Dx = 1.368 Mg m3
Hall symbol: P 2ac 2abSynchrotron radiation, λ = 0.60000 (2) Å
a = 7.875 (2) ŵ = 0.09 mm1
b = 9.892 (2) ÅT = 100 K
c = 18.843 (4) ÅPlate, colourless
V = 1467.9 (6) Å30.6 × 0.4 × 0.1 mm
Data collection top
Huber
diffractometer
11018 reflections with I > 2σ(I)
Radiation source: synchrotronRint = 0.030
Graphite monochromatorθmax = 47.0°, θmin = 1.8°
ϕ scanh = 1018
144632 measured reflectionsk = 2323
11539 independent reflectionsl = 4444
Refinement top
Refinement on F20 restraints
Least-squares matrix: fullH-atom parameters not refined
R[F2 > 2σ(F2)] = 0.018 w2 = 1/[s2(Fo2)]
wR(F2) = 0.033(Δ/σ)max < 0.001
S = 2.53Δρmax = 0.12 e Å3
11025 reflectionsΔρmin = 0.20 e Å3
535 parameters
Crystal data top
C19H14N2O2V = 1467.9 (6) Å3
Mr = 302.32Z = 4
Orthorhombic, P212121Synchrotron radiation, λ = 0.60000 (2) Å
a = 7.875 (2) ŵ = 0.09 mm1
b = 9.892 (2) ÅT = 100 K
c = 18.843 (4) Å0.6 × 0.4 × 0.1 mm
Data collection top
Huber
diffractometer
11018 reflections with I > 2σ(I)
144632 measured reflectionsRint = 0.030
11539 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0180 restraints
wR(F2) = 0.033H-atom parameters not refined
S = 2.53Δρmax = 0.12 e Å3
11025 reflectionsΔρmin = 0.20 e Å3
535 parameters
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
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)0.0820010.3975510.5853190.024
H(3)0.236620.0325760.5221530.035
H(4)0.160260.13150.6368420.038
H(6)0.0636620.2432310.7285860.032
H(82)0.4939060.3554290.6235310.028
H(83)0.6880520.4679980.7056080.033
H(84)0.5811970.6595050.7825950.038
H(85)0.2754510.7201030.7790970.037
H(86)0.0817810.602840.691880.031
H(92)0.070340.4430570.4044270.031
H(93)0.1126560.6394230.3265870.039
H(94)0.2957790.832070.3662420.040
H(95)0.4547730.815030.4772760.034
H(96)0.4199920.6129770.556130.027
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
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)0.0198660.021170.0319840.001860.0026160.004974
H(3)0.0434450.0201390.0400070.0024610.0054540.007153
H(4)0.0455730.0170920.0525250.0001970.0001060.008566
H(6)0.0381050.0334580.0241270.0020990.0053590.001695
H(82)0.0253420.0251710.0335170.0048360.0000210.007774
H(83)0.0198020.0377260.0420710.003030.0067880.002764
H(84)0.0321820.0439950.0365630.0069030.0109550.013593
H(85)0.0356630.0407270.035880.0011720.0011860.021315
H(86)0.0195550.0352370.0373780.0039090.0005230.011378
H(92)0.0370240.0259840.0304320.0099490.0083340.000253
H(93)0.050780.0390950.0278550.0088720.0141450.009439
H(94)0.0506270.0287230.0412590.0097170.0079670.017131
H(95)0.0354840.0228040.0424830.0106580.0062080.00347
H(96)0.0298530.0260810.0262160.0028420.0073530.001078
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)0.9670C(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)1.0825C(92)—H(92)1.0834
C(4)—H(4)1.0821C(93)—C(94)1.3992 (4)
C(6)—C(7)1.3903 (3)C(93)—H(93)1.0812
C(6)—H(6)1.0845C(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)106.385C(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)124.18C(81)—C(86)—H(86)117.22
C(4)—C(3)—H(3)119.83C(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)118.00N(1)—C(91)—C(96)120.604 (18)
C(3)—C(4)—H(4)117.69C(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)117.46C(91)—C(92)—H(92)120.725
C(7)—C(6)—H(6)121.19C(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)118.95C(91)—C(96)—H(96)120.167
C(83)—C(82)—H(82)120.96C(95)—C(96)—H(96)120.227

Experimental details

(I)(II)(III)
Crystal data
Chemical formulaC14H11NO2C13H10N2O2C19H14N2O2
Mr225.24226.23302.32
Crystal system, space groupOrthorhombic, PbcaMonoclinic, P21/cOrthorhombic, P212121
Temperature (K)100100100
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, 9090, 107.00 (3), 9090, 90, 90
V3)2189.1 (8)1051.0 (4)1467.9 (6)
Z844
Radiation typeSynchrotron, λ = 0.60000 (2) ÅSynchrotron, λ = 0.5000 (2) ÅSynchrotron, λ = 0.60000 (2) Å
µ (mm1)0.090.060.09
Crystal size (mm)0.5 × 0.3 × 0.150.5 × 0.4 × 0.350.6 × 0.4 × 0.1
Data collection
DiffractometerHuber
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
Rint0.0000.0310.030
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 reflections137001422711025
No. of parameters383421535
H-atom treatmentH-atom parameters not refinedH-atom parameters not refinedH-atom parameters not refined
Δρmax, Δρmin (e Å3)0.25, 0.240.29, 0.270.12, 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)0.9676C(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)1.0842C(94)—C(95)1.3977 (4)
C(4)—C(5)1.4053 (4)C(94)—H(94)1.0836
C(4)—H(4)1.0839C(95)—C(96)1.3987 (4)
C(5)—C(6)1.4012 (4)C(95)—H(95)1.0851
C(5)—H(5)1.0842C(96)—H(96)1.0850
C(6)—C(7)1.3921 (4)
C(8)—O(2)—H(2)106.899C(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)120.588C(93)—C(92)—H(92)122.729
C(4)—C(3)—H(3)122.079C(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)119.912C(94)—C(93)—H(93)119.365
C(5)—C(4)—H(4)119.391C(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)119.700C(95)—C(94)—H(94)119.099
C(6)—C(5)—H(5)119.023C(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)121.991C(96)—C(95)—H(95)119.972
C(7)—C(6)—H(6)120.273C(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)0.9660C(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)1.0810C(94)—H(94)1.0810
C(5)—C(6)1.4028 (4)C(95)—C(96)1.4016 (4)
C(5)—H(5)1.0820C(95)—H(95)1.0798
C(6)—C(7)1.3931 (4)C(96)—H(96)1.0824
C(8)—O(2)—H(2)110.128O(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)113.084C(92)—C(93)—H(93)118.707
C(5)—C(4)—H(4)123.256C(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)118.695C(93)—C(94)—H(94)120.001
C(6)—C(5)—H(5)121.212C(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)120.694C(94)—C(95)—H(95)120.822
C(7)—C(6)—H(6)123.024C(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)0.9670C(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)1.0825C(92)—H(92)1.0834
C(4)—H(4)1.0821C(93)—C(94)1.3992 (4)
C(6)—C(7)1.3903 (3)C(93)—H(93)1.0812
C(6)—H(6)1.0845C(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)106.385C(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)124.18C(81)—C(86)—H(86)117.22
C(4)—C(3)—H(3)119.83C(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)118.00N(1)—C(91)—C(96)120.604 (18)
C(3)—C(4)—H(4)117.69C(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)117.46C(91)—C(92)—H(92)120.725
C(7)—C(6)—H(6)121.19C(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)118.95C(91)—C(96)—H(96)120.167
C(83)—C(82)—H(82)120.96C(95)—C(96)—H(96)120.227
 

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