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The asymmetric unit of the title compound, C22H18N2O2, contains two crystallographically independent mol­ecules, in which each mol­ecule is composed of three planar six-membered rings and one nonplanar seven-membered ring. The six-membered A (phenol), B (fused benzene) and C (methoxyphenyl) rings are oriented with respect to each other at dihedral angles of 88.79 (3) (A/B), 68.16 (3) (A/C) and 37.51 (2)° (B/C), and 82.43 (3) (A′/B′), 78.52 (2) (A′/C′) and 28.65 (3)° (B′/C′). The seven-membered rings adopt near-boat conformations. Intra­molecular O—H...N and C—H...O hydrogen bonds are present in the crystal structure.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807034824/hk2294sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536807034824/hk2294Isup2.hkl
Contains datablock I

CCDC reference: 657837

Key indicators

  • Single-crystal X-ray study
  • T = 298 K
  • Mean [sigma](C-C) = 0.002 Å
  • R factor = 0.041
  • wR factor = 0.120
  • Data-to-parameter ratio = 17.5

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT230_ALERT_2_C Hirshfeld Test Diff for C25 - C26 .. 6.72 su PLAT410_ALERT_2_C Short Intra H...H Contact H31B .. H44A .. 1.98 Ang.
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 2 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 2 ALERT type 2 Indicator that the structure model may be wrong or deficient 0 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

The title compound belongs to an important class of the pharmacologically pre-eminent 1,5-benzodiazepines which are extensively studied for medicinal activities (Krapcho & Turk, 1966). In recent years, benzodiazepines have replaced barbiturates which were used once for the purpose of hypnotic effects, owing to their less toxic and less severe withdrawal effects (Gringauz, 1999). The importance of 1,5-benzodiazepines, in particular is evident from the pharmaceutical application of Globazam (Butcher & Hamor, 1985). The difficulties encountered in the cyclization of these seven-membered heterocycles limited their structural studies. In view of the importance of this class of compounds, the title compound, (I), has been synthesized and its crystal structure is reported here.

The asymmetric unit of the title compound, (I), contains two crystallographicaly independent molecules (Fig. 1). Bond lengths and angles can be regarded as normal (Cambridge Structural Database, Version 5.28, November 2006; Allen, 2002; Mogul, Version 1.1; Bruno et al., 2004). The seven membered diazepine rings have fragments N1—C12—C11—N2 and N3—C34—C33—N4, which are conjugated with the adjacent benzene rings. Like azepines, diazepines are not planar and generally adopt boat conformation (Armarego, 1977).

The rings A (C2—C7), B (C11—C16), C (C17—C22) and A' (C24—C29), B' (C33—C38), C' (C39—C44) are, of course, planar and dihedral angles between them are A/B = 88.79 (3)°, A/C = 68.16 (3)°, B/C = 37.51 (2)° and A'/B' = 82.43 (3)°, A'/C' = 78.52 (2)°, B'/C' = 28.65 (3)°. The seven membered rings D (N1/N2/C8—C12) and D' (N3/N4/C30—C34) are not planar and adopt nearly boat conformations.

The intramolecular O—H···N and C—H···O hydrogen bonds (Table 1) may be effective in the stabilization of the structure.

Related literature top

For bond-length data, see: Allen (2002); Bruno et al. (2004). For general background, see: Krapcho & Turk (1966); Gringauz (1999); Butcher & Hamor (1985); Armarego (1977). For related literature, see: Ahmed et al. (1990).

Experimental top

1-(2-hydroxyphenyl)-3-(2-methoxyphenyl)propane-1,3-dione (2.7 g, 10 mmol), prepared according to the reported procedure (Ahmed et al., 1990), was subjected to cyclo-condensation with phenylene diamine (1,08 g, 10 mmol) using toluene as solvent (100 ml) to get the title compound (yield; 69%, m.p. 439–440 K). Yellow single crystals suitable for X-ray analysis were obtained by slow evaporation of dichloromethane solution.

Refinement top

H2 and H3 (for OH groups) were located in difference syntheses and refined isotropically [O2—H2 = 0.95 (2) Å, Uiso(H) = 0.098 (7) Å2 and O3—H3 = 0.97 (2) Å, Uiso(H) = 0.093 (7) Å2]. The remaining H atoms were positioned geometrically, with C—H = 0.93, 0.97 and 0.96 Å for aromatic, methylene and methyl H atoms, and constrained to ride on their parent atoms, with Uiso(H) = xUeq(C), where x = 1.5 for methyl H, and x = 1.2 for all other H atoms.

Structure description top

The title compound belongs to an important class of the pharmacologically pre-eminent 1,5-benzodiazepines which are extensively studied for medicinal activities (Krapcho & Turk, 1966). In recent years, benzodiazepines have replaced barbiturates which were used once for the purpose of hypnotic effects, owing to their less toxic and less severe withdrawal effects (Gringauz, 1999). The importance of 1,5-benzodiazepines, in particular is evident from the pharmaceutical application of Globazam (Butcher & Hamor, 1985). The difficulties encountered in the cyclization of these seven-membered heterocycles limited their structural studies. In view of the importance of this class of compounds, the title compound, (I), has been synthesized and its crystal structure is reported here.

The asymmetric unit of the title compound, (I), contains two crystallographicaly independent molecules (Fig. 1). Bond lengths and angles can be regarded as normal (Cambridge Structural Database, Version 5.28, November 2006; Allen, 2002; Mogul, Version 1.1; Bruno et al., 2004). The seven membered diazepine rings have fragments N1—C12—C11—N2 and N3—C34—C33—N4, which are conjugated with the adjacent benzene rings. Like azepines, diazepines are not planar and generally adopt boat conformation (Armarego, 1977).

The rings A (C2—C7), B (C11—C16), C (C17—C22) and A' (C24—C29), B' (C33—C38), C' (C39—C44) are, of course, planar and dihedral angles between them are A/B = 88.79 (3)°, A/C = 68.16 (3)°, B/C = 37.51 (2)° and A'/B' = 82.43 (3)°, A'/C' = 78.52 (2)°, B'/C' = 28.65 (3)°. The seven membered rings D (N1/N2/C8—C12) and D' (N3/N4/C30—C34) are not planar and adopt nearly boat conformations.

The intramolecular O—H···N and C—H···O hydrogen bonds (Table 1) may be effective in the stabilization of the structure.

For bond-length data, see: Allen (2002); Bruno et al. (2004). For general background, see: Krapcho & Turk (1966); Gringauz (1999); Butcher & Hamor (1985); Armarego (1977). For related literature, see: Ahmed et al. (1990).

Computing details top

Data collection: SMART (Bruker, 1998); cell refinement: SAINT (Bruker, 1999); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1999); software used to prepare material for publication: SHELXTL.

Figures top
[Figure 1] Fig. 1. The molecular structure of the title molecule, with the atom-numbering scheme. Displacement ellipsoids are drawn at the 50% probability level.
[Figure 2] Fig. 2. The formation of the title compound.
2-[(1E,4E)-4-(2-Methoxyphenyl)-3H-benzo[b][1,5]diazepin-2-yl]phenol top
Crystal data top
C22H18N2O2F(000) = 1440
Mr = 342.38Dx = 1.301 Mg m3
Monoclinic, P21/cMelting point: 439(1) K
Hall symbol: -P 2ybcMo Kα radiation, λ = 0.71073 Å
a = 14.3963 (6) ÅCell parameters from 2164 reflections
b = 19.0230 (8) Åθ = 2.1–27.5°
c = 12.7651 (6) ŵ = 0.08 mm1
β = 91.305 (1)°T = 298 K
V = 3495.0 (3) Å3Block, yellow
Z = 80.32 × 0.28 × 0.26 mm
Data collection top
Bruker SMART CCD area-detector
diffractometer
8356 independent reflections
Radiation source: fine-focus sealed tube5640 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.021
ω and φ scansθmax = 28.3°, θmin = 2.4°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 1819
Tmin = 0.924, Tmax = 0.977k = 2124
21496 measured reflectionsl = 916
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)] = 0.042Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.120H atoms treated by a mixture of independent and constrained refinement
S = 1.00 w = 1/[σ2(Fo2) + (0.0559P)2 + 0.4964P]
where P = (Fo2 + 2Fc2)/3
8356 reflections(Δ/σ)max < 0.001
477 parametersΔρmax = 0.17 e Å3
0 restraintsΔρmin = 0.19 e Å3
Crystal data top
C22H18N2O2V = 3495.0 (3) Å3
Mr = 342.38Z = 8
Monoclinic, P21/cMo Kα radiation
a = 14.3963 (6) ŵ = 0.08 mm1
b = 19.0230 (8) ÅT = 298 K
c = 12.7651 (6) Å0.32 × 0.28 × 0.26 mm
β = 91.305 (1)°
Data collection top
Bruker SMART CCD area-detector
diffractometer
8356 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
5640 reflections with I > 2σ(I)
Tmin = 0.924, Tmax = 0.977Rint = 0.021
21496 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0420 restraints
wR(F2) = 0.120H atoms treated by a mixture of independent and constrained refinement
S = 1.00Δρmax = 0.17 e Å3
8356 reflectionsΔρmin = 0.19 e Å3
477 parameters
Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) 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
O10.03830 (7)0.34099 (6)0.70821 (9)0.0648 (3)
O20.41848 (8)0.44392 (7)0.86472 (11)0.0692 (3)
H20.4019 (15)0.4151 (11)0.8062 (18)0.098 (7)*
O30.02097 (8)0.52556 (7)0.61006 (10)0.0640 (3)
H30.0736 (15)0.5167 (11)0.5662 (16)0.093 (7)*
O40.43830 (8)0.65133 (7)0.77294 (10)0.0718 (3)
N10.19680 (7)0.25092 (6)0.69141 (9)0.0428 (3)
N20.32563 (8)0.37444 (6)0.72447 (9)0.0443 (3)
N30.35974 (8)0.60184 (6)0.48265 (10)0.0474 (3)
N40.18993 (7)0.52098 (5)0.54442 (9)0.0420 (3)
C10.12668 (13)0.37289 (13)0.69734 (18)0.0980 (7)
H1A0.12860.40160.63550.147*
H1B0.13790.40160.75760.147*
H1C0.17360.33710.69160.147*
C20.02081 (9)0.29743 (7)0.79152 (11)0.0461 (3)
C30.08829 (10)0.27298 (9)0.85813 (13)0.0585 (4)
H3A0.14970.28740.84890.070*
C40.06431 (12)0.22745 (9)0.93786 (13)0.0616 (4)
H4A0.10990.21150.98250.074*
C50.02575 (12)0.20512 (8)0.95271 (12)0.0578 (4)
H5A0.04140.17471.00740.069*
C60.09268 (10)0.22841 (7)0.88528 (11)0.0477 (3)
H6A0.15350.21270.89430.057*
C70.07119 (9)0.27470 (6)0.80432 (10)0.0398 (3)
C80.14392 (8)0.29780 (7)0.73142 (10)0.0396 (3)
C90.15782 (9)0.37523 (7)0.71038 (11)0.0433 (3)
H9A0.16120.38410.63570.052*
H9B0.10710.40250.73820.052*
C100.24804 (9)0.39396 (6)0.76502 (11)0.0417 (3)
C110.32698 (9)0.32981 (7)0.63671 (10)0.0419 (3)
C120.26806 (8)0.27080 (7)0.62375 (10)0.0410 (3)
C130.28398 (10)0.22507 (8)0.53994 (12)0.0508 (3)
H13A0.24890.18420.53360.061*
C140.35000 (10)0.23924 (9)0.46712 (12)0.0578 (4)
H14A0.35710.20960.41000.069*
C150.40615 (10)0.29817 (9)0.47921 (12)0.0574 (4)
H15A0.45030.30840.42940.069*
C160.39664 (9)0.34117 (8)0.56410 (12)0.0503 (3)
H16A0.43730.37870.57370.060*
C170.25098 (10)0.43259 (7)0.86479 (11)0.0462 (3)
C180.33617 (11)0.45524 (8)0.91028 (13)0.0543 (4)
C190.33710 (14)0.49073 (9)1.00579 (14)0.0688 (5)
H19A0.39320.50641.03490.083*
C200.25624 (16)0.50274 (9)1.05710 (15)0.0743 (5)
H20A0.25800.52611.12110.089*
C210.17215 (15)0.48061 (9)1.01487 (14)0.0705 (5)
H21A0.11740.48881.05020.085*
C220.16991 (12)0.44620 (8)0.91974 (13)0.0578 (4)
H22A0.11300.43170.89140.069*
C230.49355 (14)0.66690 (13)0.86386 (16)0.0896 (7)
H23A0.51300.62390.89690.134*
H23B0.45770.69400.91180.134*
H23C0.54720.69330.84410.134*
C240.40327 (10)0.70542 (8)0.71426 (14)0.0559 (4)
C250.40935 (12)0.77638 (10)0.74391 (17)0.0764 (6)
H25A0.43650.78880.80810.092*
C260.37478 (14)0.82749 (10)0.6770 (2)0.0852 (6)
H26A0.37870.87450.69680.102*
C270.33500 (13)0.81056 (9)0.58258 (18)0.0753 (5)
H27A0.31240.84570.53820.090*
C280.32851 (10)0.74105 (8)0.55344 (14)0.0571 (4)
H28A0.30120.72970.48890.068*
C290.36178 (9)0.68726 (7)0.61803 (12)0.0471 (3)
C300.35171 (9)0.61351 (7)0.58128 (11)0.0425 (3)
C310.32200 (9)0.55565 (7)0.65384 (11)0.0432 (3)
H31A0.35390.51210.63850.052*
H31B0.33450.56820.72640.052*
C320.21917 (9)0.54897 (6)0.63193 (10)0.0392 (3)
C330.25150 (9)0.49995 (7)0.46692 (10)0.0413 (3)
C340.33334 (9)0.53628 (7)0.44029 (11)0.0441 (3)
C350.38566 (11)0.51050 (8)0.35770 (12)0.0569 (4)
H35A0.43930.53420.33900.068*
C360.35971 (12)0.45104 (9)0.30367 (13)0.0637 (4)
H36A0.39740.43350.25160.076*
C370.27742 (12)0.41713 (8)0.32667 (13)0.0606 (4)
H37A0.25880.37770.28870.073*
C380.22379 (11)0.44208 (7)0.40568 (12)0.0519 (4)
H38A0.16760.42010.41910.062*
C390.15199 (9)0.57447 (7)0.70743 (11)0.0422 (3)
C400.05604 (10)0.56137 (8)0.69350 (12)0.0494 (3)
C410.00595 (11)0.58597 (10)0.76695 (14)0.0652 (4)
H41A0.06890.57610.75850.078*
C420.02448 (13)0.62447 (10)0.85140 (14)0.0698 (5)
H42A0.01800.64140.89900.084*
C430.11783 (13)0.63835 (9)0.86631 (14)0.0663 (4)
H43A0.13840.66450.92390.080*
C440.18026 (11)0.61337 (8)0.79572 (12)0.0538 (4)
H44A0.24320.62250.80680.065*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0438 (5)0.0878 (8)0.0628 (7)0.0181 (5)0.0026 (5)0.0208 (6)
O20.0564 (7)0.0758 (8)0.0750 (8)0.0069 (6)0.0080 (6)0.0162 (7)
O30.0425 (6)0.0874 (8)0.0620 (7)0.0059 (5)0.0029 (5)0.0114 (6)
O40.0652 (7)0.0771 (8)0.0722 (8)0.0082 (6)0.0198 (6)0.0206 (6)
N10.0391 (6)0.0400 (6)0.0493 (7)0.0002 (4)0.0022 (5)0.0001 (5)
N20.0435 (6)0.0420 (6)0.0474 (7)0.0035 (5)0.0002 (5)0.0011 (5)
N30.0473 (6)0.0432 (6)0.0521 (7)0.0064 (5)0.0072 (5)0.0041 (5)
N40.0427 (6)0.0381 (6)0.0452 (6)0.0036 (4)0.0023 (5)0.0021 (5)
C10.0623 (11)0.1324 (19)0.0994 (16)0.0450 (12)0.0042 (11)0.0306 (14)
C20.0424 (7)0.0522 (8)0.0437 (8)0.0031 (6)0.0032 (6)0.0023 (6)
C30.0435 (8)0.0716 (10)0.0607 (10)0.0048 (7)0.0122 (7)0.0038 (8)
C40.0651 (10)0.0660 (10)0.0547 (9)0.0082 (8)0.0222 (8)0.0035 (8)
C50.0714 (10)0.0551 (9)0.0472 (9)0.0060 (7)0.0047 (8)0.0063 (7)
C60.0480 (7)0.0443 (7)0.0506 (8)0.0019 (6)0.0031 (6)0.0007 (6)
C70.0396 (6)0.0369 (6)0.0429 (7)0.0017 (5)0.0002 (5)0.0038 (6)
C80.0354 (6)0.0390 (6)0.0441 (7)0.0000 (5)0.0037 (5)0.0008 (6)
C90.0417 (7)0.0383 (7)0.0497 (8)0.0034 (5)0.0006 (6)0.0040 (6)
C100.0467 (7)0.0314 (6)0.0469 (8)0.0015 (5)0.0003 (6)0.0063 (6)
C110.0370 (6)0.0454 (7)0.0432 (7)0.0030 (5)0.0022 (6)0.0035 (6)
C120.0362 (6)0.0434 (7)0.0432 (7)0.0042 (5)0.0006 (5)0.0010 (6)
C130.0413 (7)0.0551 (8)0.0557 (9)0.0036 (6)0.0019 (6)0.0099 (7)
C140.0463 (8)0.0774 (11)0.0497 (9)0.0111 (7)0.0002 (7)0.0134 (8)
C150.0419 (8)0.0804 (11)0.0503 (9)0.0075 (7)0.0088 (7)0.0053 (8)
C160.0377 (7)0.0576 (9)0.0556 (9)0.0012 (6)0.0024 (6)0.0067 (7)
C170.0566 (8)0.0346 (7)0.0475 (8)0.0002 (6)0.0013 (6)0.0043 (6)
C180.0629 (9)0.0440 (8)0.0557 (9)0.0010 (7)0.0057 (8)0.0008 (7)
C190.0870 (13)0.0557 (10)0.0631 (11)0.0022 (9)0.0127 (10)0.0091 (8)
C200.1116 (16)0.0561 (10)0.0551 (10)0.0029 (10)0.0012 (11)0.0098 (8)
C210.0915 (13)0.0573 (10)0.0635 (11)0.0058 (9)0.0200 (10)0.0020 (8)
C220.0659 (10)0.0474 (8)0.0605 (10)0.0000 (7)0.0090 (8)0.0006 (7)
C230.0719 (12)0.1237 (18)0.0724 (13)0.0040 (11)0.0153 (10)0.0411 (13)
C240.0391 (7)0.0593 (9)0.0694 (10)0.0088 (6)0.0057 (7)0.0184 (8)
C250.0629 (10)0.0737 (12)0.0928 (14)0.0171 (9)0.0091 (10)0.0399 (11)
C260.0800 (13)0.0479 (10)0.1281 (19)0.0087 (9)0.0134 (13)0.0257 (12)
C270.0713 (11)0.0462 (9)0.1090 (16)0.0036 (8)0.0178 (11)0.0067 (10)
C280.0502 (8)0.0459 (8)0.0757 (11)0.0070 (6)0.0134 (8)0.0019 (8)
C290.0354 (6)0.0460 (7)0.0604 (9)0.0094 (5)0.0117 (6)0.0106 (7)
C300.0338 (6)0.0433 (7)0.0505 (8)0.0050 (5)0.0030 (6)0.0057 (6)
C310.0431 (7)0.0414 (7)0.0450 (8)0.0022 (5)0.0051 (6)0.0006 (6)
C320.0432 (7)0.0312 (6)0.0429 (7)0.0039 (5)0.0019 (6)0.0035 (5)
C330.0445 (7)0.0372 (6)0.0418 (7)0.0027 (5)0.0055 (6)0.0009 (6)
C340.0486 (7)0.0407 (7)0.0428 (7)0.0013 (6)0.0004 (6)0.0021 (6)
C350.0570 (9)0.0615 (9)0.0523 (9)0.0014 (7)0.0078 (7)0.0054 (8)
C360.0746 (11)0.0649 (10)0.0517 (9)0.0137 (8)0.0055 (8)0.0133 (8)
C370.0765 (11)0.0498 (9)0.0551 (10)0.0038 (8)0.0088 (8)0.0147 (7)
C380.0569 (8)0.0454 (8)0.0529 (9)0.0017 (6)0.0088 (7)0.0060 (7)
C390.0472 (7)0.0376 (7)0.0416 (7)0.0015 (5)0.0015 (6)0.0058 (6)
C400.0463 (8)0.0545 (8)0.0473 (8)0.0024 (6)0.0006 (6)0.0076 (7)
C410.0482 (8)0.0863 (12)0.0614 (11)0.0079 (8)0.0052 (8)0.0049 (9)
C420.0720 (11)0.0819 (12)0.0561 (10)0.0181 (9)0.0151 (9)0.0007 (9)
C430.0770 (12)0.0682 (10)0.0539 (10)0.0026 (9)0.0079 (8)0.0107 (8)
C440.0574 (9)0.0540 (9)0.0503 (9)0.0043 (7)0.0037 (7)0.0048 (7)
Geometric parameters (Å, º) top
C1—O11.4135 (19)C23—H23A0.9600
C1—H1A0.9600C23—H23B0.9600
C1—H1B0.9600C23—H23C0.9600
C1—H1C0.9600C24—O41.363 (2)
C2—O11.3670 (17)C24—C291.397 (2)
C2—C31.386 (2)C24—C251.404 (2)
C2—C71.3993 (18)C25—C261.380 (3)
C3—C41.375 (2)C25—H25A0.9300
C3—H3A0.9300C26—C271.361 (3)
C4—C51.373 (2)C26—H26A0.9300
C4—H4A0.9300C27—C281.376 (2)
C5—C61.380 (2)C27—H27A0.9300
C5—H5A0.9300C28—C291.392 (2)
C6—C71.3873 (19)C28—H28A0.9300
C6—H6A0.9300C29—C301.4852 (18)
C7—C81.4831 (18)C30—N31.2863 (17)
C8—N11.2859 (16)C30—C311.5068 (19)
C8—C91.5114 (18)C31—C321.5057 (18)
C9—C101.5030 (18)C31—H31A0.9700
C9—H9A0.9700C31—H31B0.9700
C9—H9B0.9700C32—N41.2989 (16)
C10—N21.2961 (17)C32—C391.4636 (19)
C10—C171.470 (2)C33—N41.4015 (17)
C11—C161.3978 (19)C33—C381.4028 (19)
C11—N21.4061 (17)C33—C341.4140 (19)
C11—C121.4144 (18)C34—C351.398 (2)
C12—C131.4019 (19)C34—N31.4082 (17)
C12—N11.4077 (17)C35—C361.372 (2)
C13—C141.371 (2)C35—H35A0.9300
C13—H13A0.9300C36—C371.386 (2)
C14—C151.389 (2)C36—H36A0.9300
C14—H14A0.9300C37—C381.369 (2)
C15—C161.367 (2)C37—H37A0.9300
C15—H15A0.9300C38—H38A0.9300
C16—H16A0.9300C39—C441.401 (2)
C17—C221.399 (2)C39—C401.4108 (19)
C17—C181.412 (2)C40—O31.3524 (18)
C18—O21.349 (2)C40—C411.390 (2)
C18—C191.393 (2)C41—C421.367 (3)
C19—C201.368 (3)C41—H41A0.9300
C19—H19A0.9300C42—C431.379 (3)
C20—C211.380 (3)C42—H42A0.9300
C20—H20A0.9300C43—C441.372 (2)
C21—C221.379 (2)C43—H43A0.9300
C21—H21A0.9300C44—H44A0.9300
C22—H22A0.9300O2—H20.95 (2)
C23—O41.423 (2)O3—H30.97 (2)
O1—C1—H1A109.5H23A—C23—H23C109.5
O1—C1—H1B109.5H23B—C23—H23C109.5
H1A—C1—H1B109.5O4—C24—C29116.23 (13)
O1—C1—H1C109.5O4—C24—C25123.90 (16)
H1A—C1—H1C109.5C29—C24—C25119.84 (17)
H1B—C1—H1C109.5C26—C25—C24119.43 (18)
O1—C2—C3124.15 (13)C26—C25—H25A120.3
O1—C2—C7115.80 (12)C24—C25—H25A120.3
C3—C2—C7119.97 (14)C27—C26—C25121.33 (17)
C4—C3—C2119.87 (14)C27—C26—H26A119.3
C4—C3—H3A120.1C25—C26—H26A119.3
C2—C3—H3A120.1C26—C27—C28119.42 (19)
C5—C4—C3121.16 (15)C26—C27—H27A120.3
C5—C4—H4A119.4C28—C27—H27A120.3
C3—C4—H4A119.4C27—C28—C29121.72 (17)
C4—C5—C6119.02 (15)C27—C28—H28A119.1
C4—C5—H5A120.5C29—C28—H28A119.1
C6—C5—H5A120.5C28—C29—C24118.25 (14)
C5—C6—C7121.43 (14)C28—C29—C30118.52 (13)
C5—C6—H6A119.3C24—C29—C30123.23 (14)
C7—C6—H6A119.3N3—C30—C29117.51 (13)
C6—C7—C2118.53 (13)N3—C30—C31120.58 (12)
C6—C7—C8120.45 (12)C29—C30—C31121.52 (12)
C2—C7—C8121.00 (12)C32—C31—C30103.84 (10)
N1—C8—C7118.45 (11)C32—C31—H31A111.0
N1—C8—C9121.56 (12)C30—C31—H31A111.0
C7—C8—C9119.90 (11)C32—C31—H31B111.0
C10—C9—C8105.37 (10)C30—C31—H31B111.0
C10—C9—H9A110.7H31A—C31—H31B109.0
C8—C9—H9A110.7N4—C32—C39119.75 (11)
C10—C9—H9B110.7N4—C32—C31119.50 (12)
C8—C9—H9B110.7C39—C32—C31120.75 (12)
H9A—C9—H9B108.8N4—C33—C38116.16 (12)
N2—C10—C17118.76 (12)N4—C33—C34125.03 (12)
N2—C10—C9119.36 (12)C38—C33—C34118.52 (13)
C17—C10—C9121.87 (12)C35—C34—N3117.05 (13)
C16—C11—N2117.27 (12)C35—C34—C33118.42 (13)
C16—C11—C12118.85 (13)N3—C34—C33124.03 (12)
N2—C11—C12123.59 (12)C36—C35—C34121.53 (15)
C13—C12—N1115.82 (12)C36—C35—H35A119.2
C13—C12—C11118.28 (13)C34—C35—H35A119.2
N1—C12—C11125.80 (12)C35—C36—C37120.09 (15)
C14—C13—C12121.55 (14)C35—C36—H36A120.0
C14—C13—H13A119.2C37—C36—H36A120.0
C12—C13—H13A119.2C38—C37—C36119.59 (14)
C13—C14—C15119.61 (14)C38—C37—H37A120.2
C13—C14—H14A120.2C36—C37—H37A120.2
C15—C14—H14A120.2C37—C38—C33121.64 (15)
C16—C15—C14120.16 (14)C37—C38—H38A119.2
C16—C15—H15A119.9C33—C38—H38A119.2
C14—C15—H15A119.9C44—C39—C40117.41 (13)
C15—C16—C11121.30 (14)C44—C39—C32121.37 (12)
C15—C16—H16A119.4C40—C39—C32121.22 (12)
C11—C16—H16A119.4O3—C40—C41117.84 (14)
C22—C17—C18117.63 (14)O3—C40—C39122.34 (13)
C22—C17—C10121.25 (13)C41—C40—C39119.82 (14)
C18—C17—C10121.08 (13)C42—C41—C40120.87 (16)
O2—C18—C19117.61 (15)C42—C41—H41A119.6
O2—C18—C17122.49 (14)C40—C41—H41A119.6
C19—C18—C17119.90 (16)C41—C42—C43120.35 (16)
C20—C19—C18120.56 (17)C41—C42—H42A119.8
C20—C19—H19A119.7C43—C42—H42A119.8
C18—C19—H19A119.7C44—C43—C42119.61 (16)
C19—C20—C21120.72 (17)C44—C43—H43A120.2
C19—C20—H20A119.6C42—C43—H43A120.2
C21—C20—H20A119.6C43—C44—C39121.92 (15)
C22—C21—C20119.43 (18)C43—C44—H44A119.0
C22—C21—H21A120.3C39—C44—H44A119.0
C20—C21—H21A120.3C8—N1—C12120.24 (11)
C21—C22—C17121.74 (16)C10—N2—C11121.26 (11)
C21—C22—H22A119.1C30—N3—C34119.96 (12)
C17—C22—H22A119.1C32—N4—C33121.76 (11)
O4—C23—H23A109.5C2—O1—C1119.08 (13)
O4—C23—H23B109.5C18—O2—H2102.9 (13)
H23A—C23—H23B109.5C40—O3—H3105.1 (12)
O4—C23—H23C109.5C24—O4—C23118.95 (15)
O1—C2—C3—C4177.88 (14)C25—C24—C29—C30179.36 (14)
C7—C2—C3—C41.2 (2)C28—C29—C30—N335.31 (18)
C2—C3—C4—C50.4 (2)C24—C29—C30—N3144.51 (14)
C3—C4—C5—C60.8 (2)C28—C29—C30—C31137.55 (13)
C4—C5—C6—C71.1 (2)C24—C29—C30—C3142.63 (19)
C5—C6—C7—C20.4 (2)N3—C30—C31—C3275.57 (15)
C5—C6—C7—C8178.67 (13)C29—C30—C31—C3297.07 (14)
O1—C2—C7—C6177.77 (12)C30—C31—C32—N472.36 (14)
C3—C2—C7—C60.8 (2)C30—C31—C32—C39106.82 (13)
O1—C2—C7—C80.54 (19)N4—C33—C34—C35177.08 (13)
C3—C2—C7—C8177.48 (13)C38—C33—C34—C353.49 (19)
C6—C7—C8—N147.73 (17)N4—C33—C34—N35.4 (2)
C2—C7—C8—N1130.55 (14)C38—C33—C34—N3168.15 (13)
C6—C7—C8—C9128.98 (13)N3—C34—C35—C36172.87 (14)
C2—C7—C8—C952.74 (17)C33—C34—C35—C360.7 (2)
N1—C8—C9—C1068.35 (16)C34—C35—C36—C373.5 (2)
C7—C8—C9—C10108.26 (13)C35—C36—C37—C382.0 (2)
C8—C9—C10—N274.87 (15)C36—C37—C38—C332.3 (2)
C8—C9—C10—C17103.74 (13)N4—C33—C38—C37179.17 (13)
C16—C11—C12—C131.80 (18)C34—C33—C38—C375.0 (2)
N2—C11—C12—C13171.80 (12)N4—C32—C39—C44171.24 (12)
C16—C11—C12—N1177.98 (12)C31—C32—C39—C447.94 (19)
N2—C11—C12—N14.4 (2)N4—C32—C39—C408.15 (19)
N1—C12—C13—C14178.51 (13)C31—C32—C39—C40172.67 (12)
C11—C12—C13—C144.9 (2)C44—C39—C40—O3178.72 (13)
C12—C13—C14—C153.6 (2)C32—C39—C40—O30.7 (2)
C13—C14—C15—C161.0 (2)C44—C39—C40—C411.0 (2)
C14—C15—C16—C114.2 (2)C32—C39—C40—C41179.63 (13)
N2—C11—C16—C15176.69 (13)O3—C40—C41—C42177.90 (15)
C12—C11—C16—C152.7 (2)C39—C40—C41—C421.8 (2)
N2—C10—C17—C22170.77 (13)C40—C41—C42—C431.4 (3)
C9—C10—C17—C227.85 (19)C41—C42—C43—C440.1 (3)
N2—C10—C17—C187.11 (19)C42—C43—C44—C390.7 (3)
C9—C10—C17—C18174.27 (12)C40—C39—C44—C430.3 (2)
C22—C17—C18—O2179.03 (14)C32—C39—C44—C43179.13 (14)
C10—C17—C18—O21.1 (2)C7—C8—N1—C12178.55 (11)
C22—C17—C18—C191.0 (2)C9—C8—N1—C121.89 (18)
C10—C17—C18—C19178.93 (14)C13—C12—N1—C8143.21 (13)
O2—C18—C19—C20178.76 (16)C11—C12—N1—C840.53 (19)
C17—C18—C19—C201.3 (2)C17—C10—N2—C11171.77 (11)
C18—C19—C20—C210.7 (3)C9—C10—N2—C116.89 (18)
C19—C20—C21—C220.2 (3)C16—C11—N2—C10144.76 (13)
C20—C21—C22—C170.4 (3)C12—C11—N2—C1041.54 (18)
C18—C17—C22—C210.2 (2)C29—C30—N3—C34167.67 (11)
C10—C17—C22—C21178.10 (14)C31—C30—N3—C345.27 (19)
O4—C24—C25—C26177.51 (16)C35—C34—N3—C30145.17 (14)
C29—C24—C25—C260.5 (2)C33—C34—N3—C3043.09 (19)
C24—C25—C26—C270.2 (3)C39—C32—N4—C33175.85 (11)
C25—C26—C27—C280.5 (3)C31—C32—N4—C333.34 (18)
C26—C27—C28—C290.1 (3)C38—C33—N4—C32148.59 (12)
C27—C28—C29—C240.5 (2)C34—C33—N4—C3237.68 (19)
C27—C28—C29—C30179.65 (14)C3—C2—O1—C110.8 (2)
O4—C24—C29—C28177.34 (13)C7—C2—O1—C1172.45 (16)
C25—C24—C29—C280.8 (2)C29—C24—O4—C23170.62 (14)
O4—C24—C29—C302.5 (2)C25—C24—O4—C237.5 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O2—H2···N20.95 (2)1.69 (2)2.5749 (18)154 (2)
O3—H3···N40.97 (2)1.71 (2)2.5921 (16)150.6 (18)
C9—H9B···O10.972.422.8971 (17)110
C31—H31B···O40.972.252.8830 (18)122

Experimental details

Crystal data
Chemical formulaC22H18N2O2
Mr342.38
Crystal system, space groupMonoclinic, P21/c
Temperature (K)298
a, b, c (Å)14.3963 (6), 19.0230 (8), 12.7651 (6)
β (°) 91.305 (1)
V3)3495.0 (3)
Z8
Radiation typeMo Kα
µ (mm1)0.08
Crystal size (mm)0.32 × 0.28 × 0.26
Data collection
DiffractometerBruker SMART CCD area-detector
Absorption correctionMulti-scan
(SADABS; Sheldrick, 1996)
Tmin, Tmax0.924, 0.977
No. of measured, independent and
observed [I > 2σ(I)] reflections
21496, 8356, 5640
Rint0.021
(sin θ/λ)max1)0.666
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.042, 0.120, 1.00
No. of reflections8356
No. of parameters477
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)0.17, 0.19

Computer programs: SMART (Bruker, 1998), SAINT (Bruker, 1999), SAINT, SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL (Bruker, 1999), SHELXTL.

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O2—H2···N20.95 (2)1.69 (2)2.5749 (18)154 (2)
O3—H3···N40.97 (2)1.71 (2)2.5921 (16)150.6 (18)
C9—H9B···O10.972.422.8971 (17)110
C31—H31B···O40.972.252.8830 (18)122
 

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