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The title compound, C22H19NO3, was synthesized by the reaction of 1-naphthol with ethyl cyano­acetate and benzaldehyde in ethanol under microwave irradiation. In the crystal structure, weak inter­molecular N—H...O hydrogen bonds link the mol­ecules into centrosymmetric dimers, which are held together by van der Waals forces.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805040729/cv6620sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536805040729/cv6620Isup2.hkl
Contains datablock I

CCDC reference: 296552

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.006 Å
  • R factor = 0.066
  • wR factor = 0.187
  • Data-to-parameter ratio = 14.9

checkCIF/PLATON results

No syntax errors found



Alert level C DIFMN02_ALERT_2_C The minimum difference density is < -0.1*ZMAX*0.75 _refine_diff_density_min given = -0.703 Test value = -0.600 DIFMN03_ALERT_1_C The minimum difference density is < -0.1*ZMAX*0.75 The relevant atom site should be identified. PLAT026_ALERT_3_C Ratio Observed / Unique Reflections too Low .... 48 Perc. PLAT098_ALERT_2_C Minimum (Negative) Residual Density ............ -0.70 e/A   3 PLAT199_ALERT_1_C Check the Reported _cell_measurement_temperature 293 K PLAT200_ALERT_1_C Check the Reported _diffrn_ambient_temperature . 293 K PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 3.35 Ratio PLAT222_ALERT_3_C Large Non-Solvent H Ueq(max)/Ueq(min) ... 3.37 Ratio PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 6 PLAT420_ALERT_2_C D-H Without Acceptor N1 - H0B ... ? PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........ 2
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 11 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 3 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 4 ALERT type 2 Indicator that the structure model may be wrong or deficient 3 ALERT type 3 Indicator that the structure quality may be low 1 ALERT type 4 Improvement, methodology, query or suggestion

Comment top

Benzopyrans and their derivatives exhibit useful biological and pharmacological properties (Morianka & Takahashi, 1977), acting as antisterility (Brooks, 1988) and anticancer agents (Hyana & Saimoto, 1987). In addition, polyfunctionalized benzopyrans constitute the structural unit of a number of natural products and, because of the inherent reactivity of the inbuilt pyran ring, they may serve as versatile synthons (Hatakeyama et al., 1988). We report here the crystal structure of the title compound, (I).

In the molecule of (I), (Fig. 1), all bond lengths and angles (Table 1) are normal. The intramolecular N—H···O hydrogen bond (Table 2) defines the orientation of carboxylate group. In the crystal structure, weak intermolecular N—H···O hydrogen bonds (Table 2) link the molecules into centrosymmetric dimers (Fig. 2). The crystal packing is further stabilized by van der Waals forces.

Experimental top

Compound (I) was prepared by the reaction of 1-naphthol (5 mmol) with ethyl cyanocaetate (5 mmol) and benzaldehyde (5 mmol) in ethanol (2 ml) by using piperidine (0.5 mmol) as catalyzer under microwave irradiation. The pure compound (I) was obtained by recrystallization from ethanol (m.p. 418–419 K). Crystals of (I) suitable for X-ray diffraction were obtained by slow evaporation of an ethanol solution. 1H NMR (CDCl3): δ 8.21 (d, 1H), 7.75 (d, 1H), 7.52–7.55 (m, 1H), 7.45–7.49 (m, 2H), 7.25–7.28 (m, 2H), 7.19–7.22 (m, 2H), 7.15 (d, 1H), 7.09–7.12 (m, 1H), 6.44 (s, 2H), 5.06 (s, 1H), 4.10 (m, 2H), 1.17 (t, 3H).

Refinement top

All H atoms were placed in calculated positions and refined as riding, with C—H = 0.93–0.98 Å, N—H = 0.86 Å and Uiso(H) = 1.2–1.3Ueq of the carrier atom.

Computing details top

Data collection: CAD-4 Software (Enraf–Nonius, 1989); cell refinement: CAD-4 Software; data reduction: XCAD4 (Harms & Wocadlo, 1995); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Siemens, 1996); software used to prepare material for publication: SHELXL97.

Figures top
[Figure 1] Fig. 1. View of (I), showing the labelling scheme. Displacement ellipsoids are drawn at the 30% probability level and the intramolecular hydrogen bond isindicated by a dashed line.
[Figure 2] Fig. 2. The hydrogen-bonded (dashed lines) centrosymmetric dimer in (I).
Ethyl 2-amino-4-phenyl-4H-benzo[h]chromene-3-carboxylate top
Crystal data top
C22H19NO3F(000) = 728
Mr = 345.38Dx = 1.305 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 25 reflections
a = 12.178 (2) Åθ = 9–12°
b = 8.9950 (18) ŵ = 0.09 mm1
c = 17.085 (3) ÅT = 293 K
β = 110.03 (3)°Block, colourless
V = 1758.3 (6) Å30.4 × 0.3 × 0.2 mm
Z = 4
Data collection top
Enraf–Nonius CAD-4
diffractometer
Rint = 0.070
Radiation source: fine-focus sealed tubeθmax = 26.0°, θmin = 1.8°
Graphite monochromatorh = 014
ω/2θ scansk = 010
3595 measured reflectionsl = 2019
3431 independent reflections3 standard reflections every 200 reflections
1642 reflections with I > 2σ(I) intensity decay: <1%
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.066H-atom parameters constrained
wR(F2) = 0.187 w = 1/[σ2(Fo2) + (0.05P)2 + 0.9P]
where P = (Fo2 + 2Fc2)/3
S = 1.10(Δ/σ)max < 0.001
3431 reflectionsΔρmax = 0.41 e Å3
231 parametersΔρmin = 0.70 e Å3
2 restraintsExtinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0076 (13)
Crystal data top
C22H19NO3V = 1758.3 (6) Å3
Mr = 345.38Z = 4
Monoclinic, P21/cMo Kα radiation
a = 12.178 (2) ŵ = 0.09 mm1
b = 8.9950 (18) ÅT = 293 K
c = 17.085 (3) Å0.4 × 0.3 × 0.2 mm
β = 110.03 (3)°
Data collection top
Enraf–Nonius CAD-4
diffractometer
Rint = 0.070
3595 measured reflections3 standard reflections every 200 reflections
3431 independent reflections intensity decay: <1%
1642 reflections with I > 2σ(I)
Refinement top
R[F2 > 2σ(F2)] = 0.0662 restraints
wR(F2) = 0.187H-atom parameters constrained
S = 1.10Δρmax = 0.41 e Å3
3431 reflectionsΔρmin = 0.70 e Å3
231 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
O10.8361 (2)0.8807 (3)0.04636 (16)0.0640 (8)
O20.9300 (2)0.6623 (3)0.03046 (18)0.0698 (9)
O30.7024 (2)0.4972 (3)0.08534 (15)0.0522 (7)
N10.8432 (3)0.4415 (4)0.03706 (19)0.0583 (9)
H0A0.89420.45890.01370.070*
H0B0.83460.35290.05290.070*
C10.8456 (5)1.0476 (7)0.1494 (4)0.134
H1A0.88701.07340.18620.175*
H1B0.84591.13070.11410.175*
H1C0.76641.02190.18150.175*
C20.9017 (4)0.9228 (6)0.0990 (3)0.0918 (17)
H2A0.98090.94910.06490.110*
H2B0.90520.83990.13440.110*
C30.8555 (3)0.7402 (5)0.0175 (2)0.0502 (10)
C40.7801 (3)0.6971 (4)0.0276 (2)0.0423 (9)
C50.7774 (3)0.5521 (4)0.0488 (2)0.0430 (9)
C60.7061 (3)0.8130 (4)0.0512 (2)0.0430 (9)
H6A0.66910.87600.00250.052*
C70.7779 (3)0.9122 (4)0.1227 (2)0.0403 (9)
C80.8500 (3)0.8493 (4)0.1960 (2)0.0489 (10)
H8A0.85700.74630.19980.059*
C90.9120 (3)0.9347 (5)0.2639 (2)0.0557 (11)
H9A0.96000.88940.31250.067*
C100.9024 (3)1.0877 (5)0.2592 (3)0.0581 (11)
H10A0.94361.14660.30450.070*
C110.8313 (4)1.1514 (5)0.1866 (3)0.0704 (13)
H11A0.82431.25430.18300.085*
C120.7702 (3)1.0657 (5)0.1195 (2)0.0568 (11)
H12A0.72281.11160.07090.068*
C130.6109 (3)0.7379 (4)0.0746 (2)0.0414 (9)
C140.5176 (3)0.8226 (5)0.0840 (2)0.0559 (11)
H14A0.51250.92370.07190.067*
C150.4356 (3)0.7575 (6)0.1105 (3)0.0637 (12)
H15A0.37470.81480.11520.076*
C160.4411 (3)0.6053 (6)0.1309 (2)0.0580 (11)
C170.3603 (4)0.5362 (7)0.1625 (3)0.0739 (15)
H17A0.30040.59240.16970.089*
C180.3687 (4)0.3905 (7)0.1823 (3)0.0817 (16)
H18A0.31560.34820.20400.098*
C190.4562 (4)0.3026 (6)0.1707 (3)0.0759 (15)
H19A0.46000.20190.18360.091*
C200.5367 (3)0.3634 (5)0.1402 (2)0.0610 (11)
H20A0.59470.30400.13260.073*
C210.5316 (3)0.5170 (5)0.1202 (2)0.0491 (10)
C220.6143 (3)0.5908 (5)0.0921 (2)0.0445 (9)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0652 (18)0.078 (2)0.0626 (18)0.0024 (16)0.0397 (15)0.0154 (16)
O20.0593 (17)0.087 (2)0.081 (2)0.0081 (17)0.0465 (16)0.0026 (17)
O30.0465 (15)0.0556 (17)0.0611 (16)0.0085 (13)0.0269 (13)0.0081 (14)
N10.055 (2)0.061 (2)0.068 (2)0.0148 (18)0.0324 (18)0.0043 (18)
C10.1400.1330.1830.0860.1230.115
C20.085 (3)0.120 (5)0.092 (4)0.003 (3)0.058 (3)0.026 (3)
C30.046 (2)0.066 (3)0.042 (2)0.003 (2)0.0195 (18)0.003 (2)
C40.0343 (19)0.059 (3)0.0363 (19)0.0030 (17)0.0158 (16)0.0048 (18)
C50.037 (2)0.054 (3)0.039 (2)0.0048 (18)0.0142 (16)0.0022 (18)
C60.0370 (19)0.057 (2)0.0356 (19)0.0089 (18)0.0134 (15)0.0083 (18)
C70.0378 (19)0.047 (2)0.041 (2)0.0058 (17)0.0206 (16)0.0032 (18)
C80.051 (2)0.046 (2)0.047 (2)0.0048 (19)0.0124 (19)0.0046 (19)
C90.050 (2)0.064 (3)0.048 (2)0.003 (2)0.0105 (19)0.003 (2)
C100.050 (2)0.066 (3)0.057 (3)0.009 (2)0.018 (2)0.009 (2)
C110.086 (3)0.046 (3)0.081 (3)0.002 (2)0.032 (3)0.002 (2)
C120.063 (3)0.052 (3)0.052 (2)0.006 (2)0.016 (2)0.007 (2)
C130.0345 (19)0.055 (2)0.0336 (18)0.0043 (18)0.0102 (15)0.0004 (18)
C140.044 (2)0.071 (3)0.054 (2)0.010 (2)0.0197 (19)0.003 (2)
C150.040 (2)0.094 (4)0.062 (3)0.009 (2)0.024 (2)0.009 (3)
C160.034 (2)0.100 (4)0.041 (2)0.009 (2)0.0138 (17)0.010 (2)
C170.047 (3)0.120 (5)0.059 (3)0.016 (3)0.024 (2)0.014 (3)
C180.051 (3)0.139 (5)0.061 (3)0.028 (3)0.027 (2)0.002 (3)
C190.067 (3)0.100 (4)0.055 (3)0.033 (3)0.014 (2)0.012 (3)
C200.053 (2)0.079 (3)0.050 (2)0.008 (2)0.017 (2)0.003 (2)
C210.038 (2)0.075 (3)0.0331 (19)0.009 (2)0.0103 (16)0.001 (2)
C220.0332 (19)0.065 (3)0.0358 (19)0.0050 (18)0.0122 (15)0.0033 (19)
Geometric parameters (Å, º) top
O1—C31.348 (5)C9—C101.382 (6)
O1—C21.443 (4)C9—H9A0.9300
O2—C31.225 (4)C10—C111.371 (6)
O3—C51.363 (4)C10—H10A0.9300
O3—C221.399 (4)C11—C121.370 (6)
N1—C51.335 (4)C11—H11A0.9300
N1—H0A0.8600C12—H12A0.9300
N1—H0B0.8600C13—C221.354 (5)
C1—C21.437 (5)C13—C141.422 (5)
C1—H1A0.9600C14—C151.361 (5)
C1—H1B0.9600C14—H14A0.9300
C1—H1C0.9600C15—C161.409 (6)
C2—H2A0.9700C15—H15A0.9300
C2—H2B0.9700C16—C171.417 (6)
C3—C41.438 (5)C16—C211.421 (5)
C4—C51.357 (5)C17—C181.349 (7)
C4—C61.520 (5)C17—H17A0.9300
C6—C131.509 (5)C18—C191.395 (7)
C6—C71.524 (5)C18—H18A0.9300
C6—H6A0.9800C19—C201.371 (5)
C7—C81.381 (5)C19—H19A0.9300
C7—C121.384 (5)C20—C211.419 (6)
C8—C91.380 (5)C20—H20A0.9300
C8—H8A0.9300C21—C221.420 (5)
C3—O1—C2114.1 (3)C10—C9—H9A120.2
C5—O3—C22118.2 (3)C11—C10—C9118.9 (4)
C5—N1—H0A120.0C11—C10—H10A120.5
C5—N1—H0B120.0C9—C10—H10A120.5
H0A—N1—H0B120.0C12—C11—C10121.1 (4)
C2—C1—H1A109.5C12—C11—H11A119.5
C2—C1—H1B109.5C10—C11—H11A119.5
H1A—C1—H1B109.5C11—C12—C7121.1 (4)
C2—C1—H1C109.5C11—C12—H12A119.4
H1A—C1—H1C109.5C7—C12—H12A119.4
H1B—C1—H1C109.5C22—C13—C14117.6 (3)
C1—C2—O1109.1 (4)C22—C13—C6121.8 (3)
C1—C2—H2A109.9C14—C13—C6120.4 (3)
O1—C2—H2A109.9C15—C14—C13120.8 (4)
C1—C2—H2B109.9C15—C14—H14A119.6
O1—C2—H2B109.9C13—C14—H14A119.6
H2A—C2—H2B108.3C14—C15—C16121.5 (4)
O2—C3—O1121.2 (4)C14—C15—H15A119.2
O2—C3—C4126.2 (4)C16—C15—H15A119.2
O1—C3—C4112.6 (3)C15—C16—C17122.8 (4)
C5—C4—C3118.7 (3)C15—C16—C21118.9 (4)
C5—C4—C6121.1 (3)C17—C16—C21118.3 (5)
C3—C4—C6120.2 (3)C18—C17—C16121.3 (5)
N1—C5—C4127.3 (3)C18—C17—H17A119.3
N1—C5—O3109.2 (3)C16—C17—H17A119.3
C4—C5—O3123.5 (3)C17—C18—C19120.7 (5)
C13—C6—C4110.1 (3)C17—C18—H18A119.7
C13—C6—C7109.4 (3)C19—C18—H18A119.7
C4—C6—C7112.6 (3)C20—C19—C18120.6 (5)
C13—C6—H6A108.2C20—C19—H19A119.7
C4—C6—H6A108.2C18—C19—H19A119.7
C7—C6—H6A108.2C19—C20—C21120.1 (4)
C8—C7—C12117.3 (4)C19—C20—H20A119.9
C8—C7—C6120.0 (3)C21—C20—H20A119.9
C12—C7—C6122.7 (3)C20—C21—C22124.0 (4)
C9—C8—C7121.9 (4)C20—C21—C16119.0 (4)
C9—C8—H8A119.0C22—C21—C16117.0 (4)
C7—C8—H8A119.0C13—C22—O3122.4 (3)
C8—C9—C10119.7 (4)C13—C22—C21124.0 (4)
C8—C9—H9A120.2O3—C22—C21113.5 (3)
C3—O1—C2—C1159.1 (5)C7—C6—C13—C22108.5 (4)
C2—O1—C3—O25.7 (5)C4—C6—C13—C14168.2 (3)
C2—O1—C3—C4174.1 (3)C7—C6—C13—C1467.5 (4)
O2—C3—C4—C59.8 (6)C22—C13—C14—C150.6 (5)
O1—C3—C4—C5169.9 (3)C6—C13—C14—C15175.5 (3)
O2—C3—C4—C6169.7 (4)C13—C14—C15—C161.2 (6)
O1—C3—C4—C610.6 (5)C14—C15—C16—C17176.8 (4)
C3—C4—C5—N14.4 (6)C14—C15—C16—C212.6 (6)
C6—C4—C5—N1175.1 (3)C15—C16—C17—C18179.2 (4)
C3—C4—C5—O3174.4 (3)C21—C16—C17—C180.2 (6)
C6—C4—C5—O36.1 (5)C16—C17—C18—C191.3 (7)
C22—O3—C5—N1171.0 (3)C17—C18—C19—C201.2 (7)
C22—O3—C5—C48.1 (5)C18—C19—C20—C210.0 (6)
C5—C4—C6—C1317.0 (5)C19—C20—C21—C22176.9 (3)
C3—C4—C6—C13163.5 (3)C19—C20—C21—C161.1 (5)
C5—C4—C6—C7105.4 (4)C15—C16—C21—C20179.6 (4)
C3—C4—C6—C774.1 (4)C17—C16—C21—C201.0 (5)
C13—C6—C7—C869.8 (4)C15—C16—C21—C222.3 (5)
C4—C6—C7—C852.9 (4)C17—C16—C21—C22177.2 (3)
C13—C6—C7—C12106.9 (4)C14—C13—C22—O3179.7 (3)
C4—C6—C7—C12130.4 (4)C6—C13—C22—O33.6 (5)
C12—C7—C8—C90.3 (5)C14—C13—C22—C210.8 (5)
C6—C7—C8—C9176.6 (3)C6—C13—C22—C21175.2 (3)
C7—C8—C9—C100.0 (6)C5—O3—C22—C139.4 (5)
C8—C9—C10—C110.1 (6)C5—O3—C22—C21171.7 (3)
C9—C10—C11—C120.1 (6)C20—C21—C22—C13178.7 (4)
C10—C11—C12—C70.3 (6)C16—C21—C22—C130.6 (5)
C8—C7—C12—C110.4 (6)C20—C21—C22—O30.3 (5)
C6—C7—C12—C11176.4 (3)C16—C21—C22—O3178.4 (3)
C4—C6—C13—C2215.8 (5)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H0A···O20.862.082.688 (4)127
N1—H0A···O2i0.862.332.954 (4)130
Symmetry code: (i) x+2, y+1, z.

Experimental details

Crystal data
Chemical formulaC22H19NO3
Mr345.38
Crystal system, space groupMonoclinic, P21/c
Temperature (K)293
a, b, c (Å)12.178 (2), 8.9950 (18), 17.085 (3)
β (°) 110.03 (3)
V3)1758.3 (6)
Z4
Radiation typeMo Kα
µ (mm1)0.09
Crystal size (mm)0.4 × 0.3 × 0.2
Data collection
DiffractometerEnraf–Nonius CAD-4
diffractometer
Absorption correction
No. of measured, independent and
observed [I > 2σ(I)] reflections
3595, 3431, 1642
Rint0.070
(sin θ/λ)max1)0.616
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.066, 0.187, 1.10
No. of reflections3431
No. of parameters231
No. of restraints2
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.41, 0.70

Computer programs: CAD-4 Software (Enraf–Nonius, 1989), CAD-4 Software, XCAD4 (Harms & Wocadlo, 1995), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL (Siemens, 1996), SHELXL97.

Selected geometric parameters (Å, º) top
O1—C31.348 (5)N1—C51.335 (4)
O1—C21.443 (4)C1—C21.437 (5)
O2—C31.225 (4)C3—C41.438 (5)
O3—C51.363 (4)C6—C71.524 (5)
O3—C221.399 (4)
C3—O1—C2114.1 (3)C4—C5—O3123.5 (3)
C5—O3—C22118.2 (3)C13—C6—C7109.4 (3)
C1—C2—O1109.1 (4)C4—C6—C7112.6 (3)
O2—C3—O1121.2 (4)C8—C7—C6120.0 (3)
O2—C3—C4126.2 (4)C12—C7—C6122.7 (3)
O1—C3—C4112.6 (3)C14—C13—C6120.4 (3)
C5—C4—C3118.7 (3)C20—C21—C22124.0 (4)
C3—C4—C6120.2 (3)C13—C22—O3122.4 (3)
N1—C5—C4127.3 (3)O3—C22—C21113.5 (3)
N1—C5—O3109.2 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H0A···O20.862.082.688 (4)127
N1—H0A···O2i0.862.332.954 (4)130
Symmetry code: (i) x+2, y+1, z.
 

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