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The title compound, C19H16N2O, is a Reissert compound. The heterocyclic fragment of the mol­ecule exhibits a 1,3-diplanar conformation. The phenyl ring is connected to the isoquinoline ring system via an amide bond that adopts an anti conformation with respect to the adjacent C—N bond in the adjacent heterocyclic ring. Intra- and inter­molecular C—H...O hydrogen bonds are present in the crystal structure.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807027729/wn2150sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536807027729/wn2150Isup2.hkl
Contains datablock I

CCDC reference: 654917

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.002 Å
  • R factor = 0.047
  • wR factor = 0.133
  • Data-to-parameter ratio = 15.3

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT180_ALERT_3_C Check Cell Rounding: # of Values Ending with 0 = 4 PLAT230_ALERT_2_C Hirshfeld Test Diff for C6 - C19 .. 6.68 su
Alert level G PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature 293 K PLAT200_ALERT_1_G Check the Reported _diffrn_ambient_temperature . 293 K PLAT793_ALERT_1_G Check the Absolute Configuration of C6 = ... R
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 2 ALERT level C = Check and explain 3 ALERT level G = General alerts; check 3 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 1 ALERT type 2 Indicator that the structure model may be wrong or deficient 1 ALERT type 3 Indicator that the structure quality may be low 0 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check

Comment top

Reissert compounds are of major synthetic interest as reagents for different synthetic pathways, such as alkylation, condensation with aldehydes and ketones, rearrangements and conjugate additions (Cooney, 1983).

2-Benzoyl-1-cyano-8-ethyl-1,2-dihydroisoquinoline, is a Reissert compound. As expected, bond lengths and angles are similar to those observed in the analogue with no ethyl group at C4 (Tykarska et al., 1985). All bond lengths of the nitrogen-containing six-membered ring of the isoquinoline group are different, ranging from 1.330 (2) Å to 1.515 (2) Å and are significantly different from those observed in the tetrahydrogenated non-ethylated derivative (Pływaczyk et al., 1984). Bond angles at N1, C5, C7, C8, C9 (ranging from 116.3 (1)° to 121.1 (1)°) are typical for sp2 hybridization. The N1—C6—C5 angle is significantly smaller (111.7 (1)°), approaching, as expected, the classical value for an sp3 hybridization. The heterocyclic ring molecule exhibits a 1,3-diplanar conformation.

The phenyl ring is connected to the isoquinoline unit via an amide bond that adopts an anti conformation with respect to the adjacent C7—N1 bond. Coplanarity of the aromatic system of the isoquinoline moiety and the amide group allows maximum conjugation. In contrast, the amide group and the phenyl ring are not conjugated, with an N1—C10—C11—C12 torsion angle of 140.6 (1)°. A similar conformation is observed for the unsubstituted analogue, 2-benzoyl-1-cyano-1,2-dihydroisoquinoline.

Interestingly, the ethyl group is almost perpendicular to the dihydroisoquinoline system (C3—C4—C17—C18 = -105.7 (2)°) and points in the same direction as the cyano group.

Related literature top

For related literature, see: Cooney (1983); Hendrickson & Rodriguez (1983); Pływaczyk et al. (1984); Ruchirawat et al. (1977); Tykarska et al. (1985).

Experimental top

The title compound, (±)-2-benzoyl-1-cyano-8-ethyl-1,2-dihydroisoquinoline, was obtained by reaction of 8-ethyl-isoquinoline with benzoyl chloride and trimethylsilyl cyanide in anhydrous dichloromethane (Ruchirawat et al., 1977).

8-Ethylisoquinoline was prepared from 2-ethylbenzaldehyde by the Hendrickson modification of the Pomeranz-Fritsch synthesis (Hendrickson & Rodriguez, 1983).

Crystals were obtained by slow evaporation of a methanol solution at room temperature.

Refinement top

H6, attached to C6, was located in a difference map and refined freely. All other H atoms were placed at idealized positions and allowed to ride on their parent atoms, with C—H = 0.97 Å and Uiso(H) = 1.2Ueq(C) for methylene groups, C—H = 0.93 Å and Uiso(H) = 1.2Ueq(C) for aromatic carbons, and C—H = 0.96 Å and Uiso(H) = 1.5Ueq(C) for the methyl group.

Structure description top

Reissert compounds are of major synthetic interest as reagents for different synthetic pathways, such as alkylation, condensation with aldehydes and ketones, rearrangements and conjugate additions (Cooney, 1983).

2-Benzoyl-1-cyano-8-ethyl-1,2-dihydroisoquinoline, is a Reissert compound. As expected, bond lengths and angles are similar to those observed in the analogue with no ethyl group at C4 (Tykarska et al., 1985). All bond lengths of the nitrogen-containing six-membered ring of the isoquinoline group are different, ranging from 1.330 (2) Å to 1.515 (2) Å and are significantly different from those observed in the tetrahydrogenated non-ethylated derivative (Pływaczyk et al., 1984). Bond angles at N1, C5, C7, C8, C9 (ranging from 116.3 (1)° to 121.1 (1)°) are typical for sp2 hybridization. The N1—C6—C5 angle is significantly smaller (111.7 (1)°), approaching, as expected, the classical value for an sp3 hybridization. The heterocyclic ring molecule exhibits a 1,3-diplanar conformation.

The phenyl ring is connected to the isoquinoline unit via an amide bond that adopts an anti conformation with respect to the adjacent C7—N1 bond. Coplanarity of the aromatic system of the isoquinoline moiety and the amide group allows maximum conjugation. In contrast, the amide group and the phenyl ring are not conjugated, with an N1—C10—C11—C12 torsion angle of 140.6 (1)°. A similar conformation is observed for the unsubstituted analogue, 2-benzoyl-1-cyano-1,2-dihydroisoquinoline.

Interestingly, the ethyl group is almost perpendicular to the dihydroisoquinoline system (C3—C4—C17—C18 = -105.7 (2)°) and points in the same direction as the cyano group.

For related literature, see: Cooney (1983); Hendrickson & Rodriguez (1983); Pływaczyk et al. (1984); Ruchirawat et al. (1977); Tykarska et al. (1985).

Computing details top

Data collection: locally modified CAD-4 Software (Enraf–Nonius, 1989); cell refinement: SET4 (de Boer & Duisenberg, 1984); data reduction: HELENA (Spek, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: PLATON.

Figures top
[Figure 1] Fig. 1. The molecular structure of the title compound, with the atom numbering scheme. Displacement ellipsoids for non-H atoms are drawn at the 50% probability level.
(±)-2-Benzoyl-8-ethyl-1,2-dihydroisoquinoline-1-carbonitrile top
Crystal data top
C19H16N2OV = 761.0 (2) Å3
Mr = 288.34Z = 2
Triclinic, P1F(000) = 304
Hall symbol: -P 1Least Squares Treatment of 25 SET4 setting angles.
a = 7.996 (1) ÅDx = 1.258 Mg m3
b = 8.948 (1) ÅCu Kα radiation, λ = 1.54178 Å
c = 11.297 (2) ŵ = 0.62 mm1
α = 108.51 (2)°T = 293 K
β = 94.86 (1)°Prism, colourless
γ = 93.04 (1)°0.25 × 0.19 × 0.15 mm
Data collection top
Enraf–Nonius CAD-4
diffractometer
3129 independent reflections
Radiation source: sealed tube2863 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.016
Detector resolution: 18.4 pixels mm-1θmax = 75.1°, θmin = 4.2°
profile data from θ/2θ scansh = 010
Absorption correction: analytical
(de Meulenaer & Tompa, 1965)
k = 1111
Tmin = 0.870, Tmax = 0.912l = 1414
3363 measured reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.047Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.133H atoms treated by a mixture of independent and constrained refinement
S = 1.07 w = 1/[σ2(Fo2) + (0.073P)2 + 0.146P]
where P = (Fo2 + 2Fc2)/3
3129 reflections(Δ/σ)max = 0.002
204 parametersΔρmax = 0.16 e Å3
0 restraintsΔρmin = 0.27 e Å3
Crystal data top
C19H16N2Oγ = 93.04 (1)°
Mr = 288.34V = 761.0 (2) Å3
Triclinic, P1Z = 2
a = 7.996 (1) ÅCu Kα radiation
b = 8.948 (1) ŵ = 0.62 mm1
c = 11.297 (2) ÅT = 293 K
α = 108.51 (2)°0.25 × 0.19 × 0.15 mm
β = 94.86 (1)°
Data collection top
Enraf–Nonius CAD-4
diffractometer
3129 independent reflections
Absorption correction: analytical
(de Meulenaer & Tompa, 1965)
2863 reflections with I > 2σ(I)
Tmin = 0.870, Tmax = 0.912Rint = 0.016
3363 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0470 restraints
wR(F2) = 0.133H atoms treated by a mixture of independent and constrained refinement
S = 1.07Δρmax = 0.16 e Å3
3129 reflectionsΔρmin = 0.27 e Å3
204 parameters
Special details top

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su'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

Refinement. Refinement on F2 for ALL reflections except those flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The observed criterion of F2 > σ(F2) is used only for calculating -R-factor-obs etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R-factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
O10.90833 (12)0.53709 (13)0.34650 (11)0.0621 (3)
N10.62678 (12)0.54197 (12)0.32412 (9)0.0387 (3)
N20.6167 (2)0.15692 (17)0.30988 (14)0.0725 (5)
C10.16240 (19)0.39167 (19)0.10521 (15)0.0571 (5)
C20.1597 (2)0.3137 (2)0.02105 (17)0.0689 (6)
C30.3059 (2)0.2683 (2)0.07305 (14)0.0633 (5)
C40.46169 (19)0.29521 (15)0.00046 (12)0.0480 (4)
C50.46170 (16)0.37120 (14)0.12923 (11)0.0390 (3)
C60.61905 (16)0.39340 (14)0.21979 (11)0.0399 (3)
C70.47592 (15)0.57954 (14)0.37858 (12)0.0394 (3)
C80.32744 (16)0.51787 (15)0.31459 (12)0.0426 (4)
C90.31451 (16)0.42280 (15)0.18231 (12)0.0421 (4)
C100.78571 (15)0.60681 (15)0.38120 (12)0.0416 (4)
C110.80173 (15)0.76349 (14)0.48144 (11)0.0390 (3)
C120.91843 (17)0.78653 (17)0.58549 (14)0.0515 (4)
C130.9493 (2)0.9350 (2)0.67430 (15)0.0610 (5)
C140.8673 (2)1.06002 (18)0.65893 (15)0.0576 (5)
C150.7526 (2)1.03744 (17)0.55620 (14)0.0546 (5)
C160.71761 (17)0.88929 (16)0.46778 (13)0.0460 (4)
C170.6199 (2)0.24568 (18)0.05984 (14)0.0588 (5)
C180.6905 (2)0.1002 (2)0.04024 (18)0.0698 (6)
C190.62085 (18)0.25958 (16)0.27124 (12)0.0480 (4)
H10.063200.423600.139200.0680*
H20.057900.291300.072000.0830*
H30.301300.218500.159200.0760*
H60.719 (2)0.3929 (18)0.1796 (15)0.048 (4)*
H70.480200.648400.460300.0470*
H80.230200.535700.354900.0510*
H120.975300.702500.595200.0620*
H131.025800.950500.744700.0730*
H140.889701.160000.718300.0690*
H150.698001.122500.546000.0650*
H160.637800.874100.399300.0550*
H17A0.706000.333300.027500.0710*
H17B0.597000.226200.149400.0710*
H18A0.716000.118200.048000.1050*
H18B0.791300.079500.081000.1050*
H18C0.608700.011000.075300.1050*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0357 (5)0.0583 (6)0.0750 (7)0.0123 (4)0.0035 (5)0.0035 (5)
N10.0335 (5)0.0385 (5)0.0388 (5)0.0050 (4)0.0048 (4)0.0046 (4)
N20.0948 (11)0.0607 (8)0.0668 (9)0.0215 (8)0.0015 (8)0.0277 (7)
C10.0426 (7)0.0596 (9)0.0638 (9)0.0006 (6)0.0058 (6)0.0162 (7)
C20.0592 (10)0.0764 (11)0.0620 (10)0.0044 (8)0.0192 (8)0.0179 (8)
C30.0801 (11)0.0634 (9)0.0387 (7)0.0084 (8)0.0084 (7)0.0116 (6)
C40.0628 (9)0.0406 (6)0.0394 (6)0.0031 (6)0.0047 (6)0.0126 (5)
C50.0436 (6)0.0347 (6)0.0384 (6)0.0000 (5)0.0026 (5)0.0125 (5)
C60.0373 (6)0.0392 (6)0.0394 (6)0.0067 (5)0.0074 (5)0.0062 (5)
C70.0378 (6)0.0392 (6)0.0396 (6)0.0078 (5)0.0086 (5)0.0086 (5)
C80.0347 (6)0.0441 (7)0.0487 (7)0.0059 (5)0.0089 (5)0.0129 (5)
C90.0396 (6)0.0395 (6)0.0468 (7)0.0003 (5)0.0001 (5)0.0151 (5)
C100.0339 (6)0.0416 (6)0.0467 (7)0.0068 (5)0.0041 (5)0.0102 (5)
C110.0326 (6)0.0402 (6)0.0423 (6)0.0016 (5)0.0044 (5)0.0107 (5)
C120.0424 (7)0.0521 (8)0.0562 (8)0.0076 (6)0.0046 (6)0.0140 (6)
C130.0528 (8)0.0674 (10)0.0496 (8)0.0018 (7)0.0100 (6)0.0051 (7)
C140.0619 (9)0.0471 (7)0.0512 (8)0.0019 (6)0.0060 (7)0.0007 (6)
C150.0657 (9)0.0417 (7)0.0552 (8)0.0108 (6)0.0076 (7)0.0127 (6)
C160.0493 (7)0.0448 (7)0.0423 (7)0.0080 (5)0.0011 (5)0.0123 (5)
C170.0764 (10)0.0545 (8)0.0418 (7)0.0044 (7)0.0193 (7)0.0085 (6)
C180.0783 (11)0.0580 (9)0.0704 (10)0.0076 (8)0.0327 (9)0.0105 (8)
C190.0515 (8)0.0451 (7)0.0420 (7)0.0140 (6)0.0013 (5)0.0065 (5)
Geometric parameters (Å, º) top
O1—C101.2161 (16)C13—C141.376 (2)
N1—C61.4644 (16)C14—C151.371 (2)
N1—C71.4086 (16)C15—C161.381 (2)
N1—C101.3830 (16)C17—C181.517 (3)
N2—C191.136 (2)C1—H10.9297
C1—C21.372 (2)C2—H20.9295
C1—C91.395 (2)C3—H30.9295
C2—C31.376 (2)C6—H60.952 (16)
C3—C41.402 (2)C7—H70.9297
C4—C51.3966 (18)C8—H80.9298
C4—C171.508 (2)C12—H120.9297
C5—C61.5150 (18)C13—H130.9297
C5—C91.3998 (18)C14—H140.9295
C6—C191.488 (2)C15—H150.9304
C7—C81.3298 (18)C16—H160.9298
C8—C91.4577 (18)C17—H17A0.9697
C10—C111.4875 (18)C17—H17B0.9699
C11—C121.3909 (19)C18—H18A0.9599
C11—C161.384 (2)C18—H18B0.9595
C12—C131.382 (2)C18—H18C0.9601
O1···C8i3.4083 (17)C19···H18Cx3.0932
O1···C193.1458 (19)H1···O1v2.6766
O1···H1i2.6766H1···H82.5458
O1···H62.297 (16)H2···H14xi2.5152
O1···H8i2.5682H3···H17B2.3539
O1···H122.7188H6···O12.297 (16)
O1···H12ii2.6267H6···C172.635 (16)
N2···C15iii3.401 (2)H6···C182.965 (17)
N1···H162.8139H6···H17A2.2203
N2···H15iii2.8074H6···H18A2.4331
N2···H7iv2.8264H7···C112.6808
C6···C183.375 (2)H7···C162.7713
C7···C7iv3.4726 (19)H7···N2iv2.8264
C7···C163.124 (2)H7···C19iv3.0707
C8···C193.337 (2)H7···H15viii2.5735
C8···O1v3.4083 (17)H8···O1v2.5682
C15···N2vi3.401 (2)H8···H12.5458
C16···C73.124 (2)H12···O12.7188
C18···C193.458 (2)H12···O1ii2.6267
C18···C63.375 (2)H14···H2xii2.5152
C19···C83.337 (2)H15···N2vi2.8074
C19···O13.1458 (19)H15···C7viii2.9866
C19···C183.458 (2)H15···H7viii2.5735
C1···H17Avii3.0312H16···N12.8139
C5···H18A3.0963H16···C72.8058
C6···H18A2.8026H17A···C62.8270
C6···H17A2.8270H17A···H62.2203
C7···H162.8058H17A···C1vii3.0312
C7···H15viii2.9866H17B···H32.3539
C11···H72.6808H18A···C53.0963
C13···H18Bix3.0669H18A···C62.8026
C14···H18Bix3.0034H18A···C192.6346
C16···H72.7713H18A···H62.4331
C17···H62.635 (16)H18B···C13xiii3.0669
C18···H62.965 (17)H18B···C14xiii3.0034
C18···H18Cx3.0853H18C···C18x3.0853
C19···H18A2.6346H18C···C19x3.0932
C19···H7iv3.0707H18C···H18Cx2.5755
C6—N1—C7116.28 (10)C9—C1—H1120.15
C6—N1—C10116.35 (10)C1—C2—H2119.61
C7—N1—C10124.71 (10)C3—C2—H2119.63
C2—C1—C9119.75 (14)C2—C3—H3119.14
C1—C2—C3120.75 (15)C4—C3—H3119.12
C2—C3—C4121.73 (14)N1—C6—H6108.1 (10)
C3—C4—C5116.80 (13)C5—C6—H6112.1 (10)
C3—C4—C17120.35 (12)C19—C6—H6106.7 (10)
C5—C4—C17122.84 (13)N1—C7—H7119.58
C4—C5—C6121.65 (12)C8—C7—H7119.57
C4—C5—C9121.83 (12)C7—C8—H8119.44
C6—C5—C9116.42 (11)C9—C8—H8119.43
N1—C6—C5111.72 (10)C11—C12—H12120.17
N1—C6—C19108.87 (10)C13—C12—H12120.22
C5—C6—C19109.26 (11)C12—C13—H13119.88
N1—C7—C8120.86 (12)C14—C13—H13119.87
C7—C8—C9121.13 (12)C13—C14—H14119.95
C1—C9—C5119.06 (12)C15—C14—H14119.92
C1—C9—C8122.04 (12)C14—C15—H15119.79
C5—C9—C8118.72 (11)C16—C15—H15119.78
O1—C10—N1119.64 (12)C11—C16—H16120.13
O1—C10—C11121.78 (12)C15—C16—H16120.09
N1—C10—C11118.56 (11)C4—C17—H17A108.32
C10—C11—C12117.94 (12)C4—C17—H17B108.33
C10—C11—C16121.96 (11)C18—C17—H17A108.28
C12—C11—C16119.77 (12)C18—C17—H17B108.29
C11—C12—C13119.61 (14)H17A—C17—H17B107.42
C12—C13—C14120.26 (15)C17—C18—H18A109.43
C13—C14—C15120.14 (15)C17—C18—H18B109.46
C14—C15—C16120.43 (15)C17—C18—H18C109.43
C11—C16—C15119.78 (13)H18A—C18—H18B109.50
C4—C17—C18115.89 (13)H18A—C18—H18C109.50
N2—C19—C6177.79 (16)H18B—C18—H18C109.51
C2—C1—H1120.10
C7—N1—C6—C543.48 (14)C4—C5—C9—C8172.67 (13)
C7—N1—C6—C1977.28 (14)C6—C5—C9—C1173.80 (13)
C10—N1—C6—C5154.13 (11)C6—C5—C9—C810.84 (19)
C10—N1—C6—C1985.12 (14)C4—C5—C6—C1993.33 (15)
C6—N1—C7—C822.81 (18)C9—C5—C6—N137.36 (16)
C10—N1—C7—C8176.44 (13)C9—C5—C6—C1983.17 (14)
C6—N1—C10—O12.57 (18)C4—C5—C9—C12.7 (2)
C6—N1—C10—C11175.59 (11)N1—C7—C8—C96.4 (2)
C7—N1—C10—O1158.17 (13)C7—C8—C9—C512.3 (2)
C7—N1—C10—C1123.67 (19)C7—C8—C9—C1162.93 (15)
C2—C1—C9—C51.1 (2)O1—C10—C11—C16132.02 (15)
C2—C1—C9—C8174.15 (15)N1—C10—C11—C12140.61 (13)
C9—C1—C2—C31.2 (3)N1—C10—C11—C1646.10 (18)
C1—C2—C3—C41.9 (3)O1—C10—C11—C1241.28 (19)
C2—C3—C4—C17179.25 (16)C10—C11—C12—C13173.43 (13)
C2—C3—C4—C50.3 (2)C16—C11—C12—C130.0 (2)
C17—C4—C5—C9176.92 (14)C10—C11—C16—C15171.86 (13)
C17—C4—C5—C66.8 (2)C12—C11—C16—C151.3 (2)
C3—C4—C5—C6174.32 (13)C11—C12—C13—C141.1 (2)
C3—C4—C17—C18105.68 (17)C12—C13—C14—C150.9 (2)
C5—C4—C17—C1875.46 (19)C13—C14—C15—C160.4 (2)
C3—C4—C5—C92.0 (2)C14—C15—C16—C111.5 (2)
C4—C5—C6—N1146.14 (12)
Symmetry codes: (i) x+1, y, z; (ii) x+2, y+1, z+1; (iii) x, y1, z; (iv) x+1, y+1, z+1; (v) x1, y, z; (vi) x, y+1, z; (vii) x+1, y+1, z; (viii) x+1, y+2, z+1; (ix) x, y+1, z+1; (x) x+1, y, z; (xi) x1, y1, z1; (xii) x+1, y+1, z+1; (xiii) x, y1, z1.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C6—H6···O10.952 (16)2.297 (16)2.6471 (17)100.9 (11)
C8—H8···O1v0.932.573.4083 (17)151
Symmetry code: (v) x1, y, z.

Experimental details

Crystal data
Chemical formulaC19H16N2O
Mr288.34
Crystal system, space groupTriclinic, P1
Temperature (K)293
a, b, c (Å)7.996 (1), 8.948 (1), 11.297 (2)
α, β, γ (°)108.51 (2), 94.86 (1), 93.04 (1)
V3)761.0 (2)
Z2
Radiation typeCu Kα
µ (mm1)0.62
Crystal size (mm)0.25 × 0.19 × 0.15
Data collection
DiffractometerEnraf–Nonius CAD-4
Absorption correctionAnalytical
(de Meulenaer & Tompa, 1965)
Tmin, Tmax0.870, 0.912
No. of measured, independent and
observed [I > 2σ(I)] reflections
3363, 3129, 2863
Rint0.016
(sin θ/λ)max1)0.627
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.047, 0.133, 1.07
No. of reflections3129
No. of parameters204
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)0.16, 0.27

Computer programs: locally modified CAD-4 Software (Enraf–Nonius, 1989), SET4 (de Boer & Duisenberg, 1984), HELENA (Spek, 1997), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), PLATON (Spek, 2003), PLATON.

Selected geometric parameters (Å, º) top
O1—C101.2161 (16)N1—C101.3830 (16)
N1—C61.4644 (16)N2—C191.136 (2)
N1—C71.4086 (16)
C6—N1—C7116.28 (10)N1—C7—C8120.86 (12)
C6—N1—C10116.35 (10)O1—C10—N1119.64 (12)
C7—N1—C10124.71 (10)O1—C10—C11121.78 (12)
N1—C6—C5111.72 (10)N1—C10—C11118.56 (11)
N1—C6—C19108.87 (10)N2—C19—C6177.79 (16)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C6—H6···O10.952 (16)2.297 (16)2.6471 (17)100.9 (11)
C8—H8···O1i0.93002.57003.4083 (17)151.00
Symmetry code: (i) x1, y, z.
 

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