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Orthophthalaldehyde (o-phthalaldehyde, OPA) is an aromatic di­aldehyde bearing two electron-withdrawing carbonyl groups. The reactions of OPA with primary amines are broadly applied for the synthesis of important heterocyclic compounds with biological relevance. A number of such reactions have been investigated recently and several structures of condensation products have been reported, however, the complex reaction mechanism is still not fully understood and comprises concurrent as well as consecutive reactions. The reaction products depend on the primary amine which reacts with OPA, the reaction environment (solvent) and the proportion of the reactants. The title mol­ecule, C11H13NO, the product of the reaction of OPA with iso­propyl­amine, contains a five-membered pyrrole C4N ring with a carbonyl substituent, which forms part of the isoindolinone unit. Though this pyrrole ring contains one C atom in the sp3-hybridized state, it is fairly planar. The title mol­ecule has been compared with similar structures retrieved from the Cambridge Structural Database in order to study this phenomenon. The planarity of this fragment has been explained by the presence of partially delocalized C—C, C—N and C—O bonds, and by an inner angle in the planar penta­gonal ring (∼108°), which is close to the ideal tetra­hedral value for the sp3-hybridized state of the constituent C atom. Due to this propitious angle, this C atom can be present in states inter­mediate between sp3- and sp2-hybridized in different structures, while still maintaining the planarity of the ring. There are only weak inter­molecular C—H...O hydrogen bonds and C—H...π-electron ring inter­actions in the structure. In particular, it is the pyrrole ring which is involved in these inter­actions.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S2053229616008767/lg3188sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2053229616008767/lg3188Isup2.hkl
Contains datablock I

smi

Smiles format file https://doi.org/10.1107/S2053229616008767/lg3188Isup3.smi
Supplementary material

cml

Chemical Markup Language (CML) file https://doi.org/10.1107/S2053229616008767/lg3188Isup4.cml
Supplementary material

CCDC reference: 1482614

Computing details top

Data collection: CrysAlis PRO (Rigaku Oxford Diffraction, 2015); cell refinement: CrysAlis PRO (Rigaku Oxford Diffraction, 2015); data reduction: CrysAlis PRO (Rigaku Oxford Diffraction, 2015); program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: JANA2006 (Petříček et al., 2014); molecular graphics: JANA2006 (Petříček et al., 2014), Origin6.1 (OriginLab Corporation, 2000) and PLATON (Spek, 2009); software used to prepare material for publication: JANA2006 (Petříček et al., 2014).

2-Isopropyl-2,3-dihydro-1H-isoindol-1-one top
Crystal data top
C11H13NOF(000) = 188
Mr = 175.2Dx = 1.240 Mg m3
Monoclinic, P21Cu Kα radiation, λ = 1.54184 Å
Hall symbol: P 2ybCell parameters from 6393 reflections
a = 6.2155 (2) Åθ = 5.1–66.9°
b = 8.7681 (3) ŵ = 0.63 mm1
c = 8.9686 (3) ÅT = 121 K
β = 106.140 (3)°Prism, orange
V = 469.51 (3) Å30.33 × 0.23 × 0.19 mm
Z = 2
Data collection top
Rigaku Oxford Diffraction Xcalibur (Atlas2, Gemini ultra)
diffractometer
1677 independent reflections
Radiation source: fine-focus sealed X-ray tube, Enhance Ultra (Cu) X-ray Source1654 reflections with I > 3σ(I)
Mirror monochromatorRint = 0.027
Detector resolution: 5.1783 pixels mm-1θmax = 67.0°, θmin = 5.1°
ω scansh = 77
Absorption correction: analytical
(CrysAlis PRO; Rigaku Oxford Diffraction, 2015)
k = 1010
Tmin = 0.86, Tmax = 0.915l = 1010
7682 measured reflections
Refinement top
Refinement on F2Weighting scheme based on measured s.u.'s w = 1/(σ2(I) + 0.0004I2)
R[F > 3σ(F)] = 0.025(Δ/σ)max = 0.009
wR(F) = 0.068Δρmax = 0.11 e Å3
S = 2.16Δρmin = 0.09 e Å3
1677 reflectionsExtinction correction: B-C type 1 Lorentzian isotropic (Becker & Coppens, 1974)
129 parametersExtinction coefficient: 850 (140)
1 restraintAbsolute structure: 775 of Friedel pairs used in the refinement
44 constraintsAbsolute structure parameter: 0.1 (2)
H atoms treated by a mixture of independent and constrained refinement
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
C10.31713 (18)0.58682 (13)0.17724 (13)0.0210 (4)
C20.1315 (2)0.56320 (14)0.05039 (13)0.0259 (4)
H20.007960.610940.0439790.0311*
C30.1580 (2)0.46724 (14)0.06641 (14)0.0302 (4)
H30.0343130.4475040.1540170.0362*
C40.3642 (2)0.39975 (15)0.05616 (15)0.0311 (4)
H40.3790950.3353590.1378980.0374*
C50.5491 (2)0.42419 (14)0.07079 (14)0.0270 (4)
H50.6892880.3775560.076880.0323*
C60.52213 (19)0.51893 (13)0.18818 (13)0.0219 (4)
C70.68645 (18)0.56549 (14)0.33849 (13)0.0220 (4)
H7a0.737 (2)0.4754 (15)0.4043 (16)0.0264*
H7b0.819 (2)0.6199 (16)0.3256 (16)0.0264*
N10.55194 (15)0.66769 (11)0.40555 (11)0.0213 (3)
C80.33519 (18)0.67937 (13)0.31837 (13)0.0210 (4)
O10.18721 (13)0.75238 (10)0.35327 (10)0.0265 (3)
C90.62791 (19)0.73006 (14)0.56327 (13)0.0238 (4)
H90.539 (3)0.8222 (19)0.5605 (17)0.0286*
C100.5737 (2)0.61960 (16)0.67849 (14)0.0321 (4)
H10a0.6292020.6610020.783720.0481*
H10b0.4111730.6053730.6533130.0481*
H10c0.6458550.5212450.6726980.0481*
C110.8742 (2)0.77187 (19)0.60473 (16)0.0395 (5)
H11a0.9180820.8202510.7072570.0593*
H11b0.9636230.6794590.6066010.0593*
H11c0.9001080.8429030.5271420.0593*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0245 (6)0.0194 (6)0.0193 (5)0.0024 (5)0.0063 (4)0.0035 (5)
C20.0257 (6)0.0260 (7)0.0238 (6)0.0018 (5)0.0031 (5)0.0027 (5)
C30.0356 (7)0.0284 (7)0.0222 (6)0.0042 (6)0.0007 (5)0.0008 (5)
C40.0450 (7)0.0251 (7)0.0232 (6)0.0042 (5)0.0093 (5)0.0031 (5)
C50.0330 (7)0.0232 (7)0.0260 (6)0.0012 (5)0.0104 (5)0.0005 (5)
C60.0252 (5)0.0200 (6)0.0214 (6)0.0021 (5)0.0079 (4)0.0024 (5)
C70.0212 (6)0.0231 (6)0.0220 (6)0.0017 (5)0.0066 (5)0.0013 (5)
N10.0214 (5)0.0235 (5)0.0191 (5)0.0011 (4)0.0057 (4)0.0023 (4)
C80.0221 (5)0.0199 (6)0.0211 (6)0.0011 (5)0.0063 (4)0.0028 (5)
O10.0231 (4)0.0295 (5)0.0275 (4)0.0040 (4)0.0082 (3)0.0002 (4)
C90.0249 (6)0.0253 (6)0.0202 (6)0.0013 (5)0.0044 (5)0.0048 (5)
C100.0395 (7)0.0357 (8)0.0208 (6)0.0036 (6)0.0081 (5)0.0016 (5)
C110.0303 (7)0.0541 (10)0.0328 (7)0.0099 (7)0.0065 (5)0.0162 (7)
Geometric parameters (Å, º) top
C1—C21.3922 (14)C7—N11.4639 (17)
C1—C61.3850 (17)N1—C81.3606 (13)
C1—C81.4812 (17)N1—C91.4668 (15)
C2—H20.95C8—O11.2304 (15)
C2—C31.3886 (18)C9—H90.975 (17)
C3—H30.95C9—C101.5209 (19)
C3—C41.391 (2)C9—C111.5165 (18)
C4—H40.95C10—H10a0.98
C4—C51.3914 (17)C10—H10b0.98
C5—H50.95C10—H10c0.98
C5—C61.3874 (18)C11—H11a0.98
C6—C71.5039 (15)C11—H11b0.98
C7—H7a0.984 (13)C11—H11c0.98
C7—H7b0.988 (14)
C2—C1—C6122.07 (11)C7—N1—C8113.41 (9)
C2—C1—C8128.94 (11)C7—N1—C9123.84 (8)
C6—C1—C8108.98 (9)C8—N1—C9121.87 (10)
C1—C2—H2121.26C1—C8—N1106.11 (10)
C1—C2—C3117.49 (11)C1—C8—O1128.17 (9)
H2—C2—C3121.26N1—C8—O1125.72 (11)
C2—C3—H3119.73N1—C9—H9104.8 (8)
C2—C3—C4120.53 (11)N1—C9—C10110.19 (10)
H3—C3—C4119.73N1—C9—C11111.04 (11)
C3—C4—H4119.17H9—C9—C10108.3 (10)
C3—C4—C5121.66 (13)H9—C9—C11109.4 (9)
H4—C4—C5119.17C10—C9—C11112.73 (10)
C4—C5—H5121.1C9—C10—H10a109.47
C4—C5—C6117.80 (12)C9—C10—H10b109.47
H5—C5—C6121.1C9—C10—H10c109.47
C1—C6—C5120.44 (10)H10a—C10—H10b109.47
C1—C6—C7109.21 (10)H10a—C10—H10c109.47
C5—C6—C7130.35 (11)H10b—C10—H10c109.47
C6—C7—H7a110.1 (7)C9—C11—H11a109.47
C6—C7—H7b114.0 (8)C9—C11—H11b109.47
C6—C7—N1102.20 (9)C9—C11—H11c109.47
H7a—C7—H7b108.6 (11)H11a—C11—H11b109.47
H7a—C7—N1111.7 (9)H11a—C11—H11c109.47
H7b—C7—N1110.1 (8)H11b—C11—H11c109.47
Hydrogen-bond geometry (Å, º) top
Cg1 is a centroid of the C1/C6/C7/N1/C8 pyrrole ring.
D—H···AD—HH···AD···AD—H···A
C3—H3···O1i0.952.583.4209 (15)148
C7—H7b···O1ii0.986 (13)2.517 (13)3.4873 (15)168.0 (11)
C9—H9···O10.975 (17)2.520 (17)2.8671 (15)100.8 (11)
C4—H4···Cg1iii0.952.693.6014 (14)160
C9—H9···Cg1iv0.975 (17)2.850 (16)3.6821 (13)143.9 (12)
Symmetry codes: (i) x, y1, z; (ii) x+1, y, z; (iii) x+1, y1/2, z; (iv) x+1, y+1/2, z+1.
The bond lengths and bond orders for selected bonds in the isoindolinone moiety of the title molecule; for the designation of the bonds, see Fig. 3. top
BondDesignationBond length (Å)Bond order
C1—C6D11.3850 (17)1.61
C1—C2D21.3922 (14)1.57
C5—C6D31.3874 (18)1.59
C2—C3D41.3886 (18)1.59
C4—C5D51.3914 (17)1.58
C3—C4D61.391 (2)1.58
C1—C8D71.4812 (17)1.23
C6—C7D81.5039 (15)1.16
C7—N1D91.4639 (17)1.06
C8—N1D101.3606 (13)1.38
C8—O1D111.2304 (15)1.79
N1—C9D121.4668 (15)1.05
The empirical bond orders for C—C, C—N and C—O (see Fig. 4) top
Bond orderC—C (Å)C—N (Å)C—O (Å)
11.54a1.462b1.435f
1.3331.291g
1.51.39a1.3362c1.251h
21.35a1.253d1.217i
31.20a1.122e
Notes and references: (a) Cram & Hammond (1969); (b) trimethylamine (Dobrzycki et al., 2015; CSD refcode DUHJIB); (c) pyridine (Mootz & Wussow, 1981; PYRDNA01); (d) azobenzene (Harada & Ogawa, 2004; AZOBEN12); (e) acetonitrile in catena-bis(µ2-acetato-O,O')tris[µ2-1,4-bis(4-pyridyl)-2,3-diaza-1,3-butadiene]bis[(µ2-thiocyanato-S,S)(µ2-thiocyanato-N,S)(thiocyanato-S)]tetramercury(II) acetonitrile solvate (Mahmoudi et al., 2009; DOMYUA); (f) determined from 58 counts from a CSD search for dimethyl ether; (g) determined from 115 counts from a CSD search for carbonate; (h) determined from 21960 counts from a CSD search for the carboxylate group; (i) determined from 8049 counts from a CSD search for an acetone molecule.
 

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