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The title compound, C22H20N2O3, was synthesized by the reaction of 4-methoxy­benz­aldehyde, 7-methoxy-2-tetralone and malono­nitrile in the presence of triethyl­benzyl­ammonium chloride in an aqueous medium. X-ray analysis reveals that the pyran ring and the fused six-membered ring adopt boat and skew-boat conformations, respectively.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536804024274/dn6161sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536804024274/dn6161Isup2.hkl
Contains datablock I

CCDC reference: 255864

Key indicators

  • Single-crystal X-ray study
  • T = 297 K
  • Mean [sigma](C-C) = 0.003 Å
  • R factor = 0.039
  • wR factor = 0.092
  • Data-to-parameter ratio = 13.4

checkCIF/PLATON results

No syntax errors found



Alert level B PLAT230_ALERT_2_B Hirshfeld Test Diff for C12 - C22 .. 8.50 su
0 ALERT level A = In general: serious problem 1 ALERT level B = Potentially serious problem 0 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 1 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

Computing details top

Data collection: XSCANS (Siemens, 1994); cell refinement: XSCANS; data reduction: SHELXTL (Sheldrick, 1997); program(s) used to solve structure: SHELXTL; program(s) used to refine structure: SHELXTL; molecular graphics: ORTEPIII (Burnett & Johnson, 1996), ORTEP-3 for Windows (Farrugia, 1997) and CAMERON (Watkin et al., 1993); software used to prepare material for publication: SHELXTL.

2-Amino-6-methoxy-4-(4-methoxyphenyl)-9,10-dihydro-4H-benzo[f]chromene- 3-carbonitrile top
Crystal data top
C22H20N2O3F(000) = 760
Mr = 360.40Dx = 1.265 Mg m3
Monoclinic, P21/cMelting point: 465 K
Hall symbol: -P 2ybcMo Kα radiation, λ = 0.71073 Å
a = 10.267 (2) ÅCell parameters from 38 reflections
b = 7.011 (1) Åθ = 3.0–13.4°
c = 26.352 (3) ŵ = 0.09 mm1
β = 93.94 (1)°T = 297 K
V = 1892.4 (5) Å3Block, colourless
Z = 40.50 × 0.36 × 0.32 mm
Data collection top
Siemens P4
diffractometer
Rint = 0.012
Radiation source: normal-focus sealed tubeθmax = 25.3°, θmin = 1.6°
Graphite monochromatorh = 012
ω scansk = 08
4089 measured reflectionsl = 3131
3424 independent reflections3 standard reflections every 97 reflections
1982 reflections with I > 2σ(I) intensity decay: 6.7%
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)] = 0.039H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.092 w = 1/[σ2(Fo2) + (0.0443P)2]
where P = (Fo2 + 2Fc2)/3
S = 0.85(Δ/σ)max < 0.001
3424 reflectionsΔρmax = 0.13 e Å3
255 parametersΔρmin = 0.12 e Å3
2 restraintsExtinction correction: SHELXTL (Sheldrick, 1997), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0110 (9)
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
O10.55965 (11)0.56348 (17)0.40812 (5)0.0548 (4)
O20.10412 (15)0.4190 (2)0.18624 (5)0.0855 (5)
O30.14968 (12)0.6129 (2)0.45355 (5)0.0672 (4)
N10.61999 (18)0.3506 (3)0.46760 (7)0.0638 (5)
N20.38465 (17)0.0303 (2)0.45513 (6)0.0655 (5)
C10.49057 (17)0.6150 (2)0.36315 (7)0.0440 (4)
C20.55173 (18)0.7821 (2)0.33962 (7)0.0538 (5)
H2A0.62100.73940.31910.065*
H2B0.58970.86540.36600.065*
C30.4503 (2)0.8905 (3)0.30662 (7)0.0592 (6)
H3A0.39700.96530.32820.071*
H3B0.49410.97800.28490.071*
C40.36354 (19)0.7597 (3)0.27399 (7)0.0508 (5)
C50.3162 (2)0.8090 (3)0.22557 (8)0.0690 (6)
H50.34240.92380.21180.083*
C60.2317 (2)0.6945 (3)0.19707 (8)0.0726 (7)
H60.20250.73090.16430.087*
C70.18990 (19)0.5251 (3)0.21697 (7)0.0600 (6)
C80.23750 (17)0.4693 (3)0.26529 (6)0.0498 (5)
H80.21040.35450.27880.060*
C90.32608 (17)0.5852 (2)0.29380 (6)0.0424 (4)
C100.38416 (17)0.5244 (2)0.34412 (6)0.0394 (4)
C110.32297 (16)0.3658 (2)0.37346 (6)0.0395 (4)
H110.30130.26080.34980.047*
C120.42317 (17)0.2936 (2)0.41403 (6)0.0405 (4)
C130.53041 (17)0.3943 (3)0.43024 (7)0.0458 (5)
C140.19714 (16)0.4328 (2)0.39540 (6)0.0384 (4)
C150.18579 (17)0.6156 (3)0.41393 (6)0.0460 (5)
H150.25670.69780.41300.055*
C160.07305 (17)0.6813 (3)0.43390 (7)0.0511 (5)
H160.06870.80550.44610.061*
C170.03256 (17)0.5616 (3)0.43564 (6)0.0484 (5)
C180.02284 (18)0.3766 (3)0.41834 (7)0.0553 (5)
H180.09280.29350.42060.066*
C190.08951 (18)0.3135 (3)0.39771 (7)0.0517 (5)
H190.09320.18970.38520.062*
C200.0475 (2)0.2551 (4)0.20630 (8)0.0930 (8)
H20A0.11420.16230.21470.112*
H20B0.01540.20250.18150.112*
H20C0.00490.28860.23640.112*
C210.1748 (2)0.8085 (3)0.46063 (9)0.0840 (7)
H21A0.11860.85620.48840.101*
H21B0.26430.82540.46810.101*
H21C0.15860.87720.43020.101*
C220.40198 (17)0.1158 (3)0.43696 (6)0.0448 (5)
H1A0.6098 (18)0.2512 (19)0.4869 (6)0.071 (7)*
H1B0.6887 (14)0.421 (2)0.4697 (8)0.083 (8)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0523 (8)0.0472 (8)0.0636 (9)0.0143 (6)0.0057 (7)0.0161 (7)
O20.0862 (11)0.1111 (13)0.0566 (9)0.0183 (11)0.0151 (8)0.0131 (10)
O30.0420 (8)0.0819 (11)0.0793 (10)0.0036 (8)0.0154 (7)0.0023 (8)
N10.0502 (11)0.0656 (13)0.0732 (12)0.0159 (10)0.0139 (10)0.0268 (10)
N20.0812 (13)0.0463 (10)0.0663 (11)0.0190 (9)0.0150 (9)0.0151 (9)
C10.0462 (11)0.0391 (10)0.0477 (11)0.0009 (9)0.0090 (9)0.0076 (9)
C20.0573 (12)0.0407 (11)0.0649 (13)0.0069 (10)0.0152 (10)0.0072 (10)
C30.0753 (14)0.0380 (11)0.0663 (13)0.0015 (11)0.0196 (11)0.0113 (10)
C40.0592 (13)0.0445 (12)0.0503 (12)0.0082 (10)0.0153 (10)0.0092 (10)
C50.0806 (16)0.0606 (14)0.0664 (15)0.0010 (13)0.0084 (13)0.0252 (12)
C60.0798 (17)0.0871 (18)0.0501 (13)0.0051 (14)0.0002 (12)0.0253 (13)
C70.0559 (13)0.0767 (16)0.0470 (12)0.0031 (12)0.0016 (10)0.0060 (12)
C80.0517 (12)0.0554 (12)0.0430 (11)0.0030 (10)0.0083 (9)0.0062 (10)
C90.0445 (10)0.0422 (11)0.0420 (10)0.0069 (9)0.0136 (9)0.0036 (9)
C100.0433 (10)0.0351 (10)0.0412 (10)0.0011 (9)0.0126 (8)0.0028 (8)
C110.0472 (10)0.0327 (10)0.0387 (10)0.0048 (8)0.0031 (8)0.0007 (8)
C120.0425 (10)0.0334 (10)0.0458 (10)0.0040 (9)0.0036 (8)0.0061 (9)
C130.0442 (11)0.0414 (11)0.0517 (11)0.0007 (10)0.0033 (9)0.0078 (9)
C140.0396 (10)0.0398 (11)0.0355 (9)0.0061 (9)0.0000 (8)0.0056 (8)
C150.0390 (11)0.0474 (11)0.0520 (11)0.0130 (9)0.0061 (9)0.0076 (9)
C160.0484 (12)0.0492 (12)0.0561 (12)0.0079 (10)0.0079 (10)0.0098 (10)
C170.0362 (11)0.0646 (13)0.0444 (11)0.0035 (10)0.0039 (8)0.0007 (10)
C180.0415 (11)0.0636 (14)0.0610 (13)0.0224 (11)0.0056 (9)0.0021 (11)
C190.0522 (12)0.0410 (11)0.0619 (12)0.0129 (10)0.0047 (10)0.0027 (10)
C200.0903 (19)0.114 (2)0.0719 (16)0.0339 (17)0.0137 (14)0.0026 (16)
C210.0605 (15)0.100 (2)0.0937 (18)0.0132 (14)0.0182 (13)0.0197 (16)
C220.0461 (11)0.0436 (11)0.0437 (11)0.0044 (10)0.0043 (9)0.0011 (9)
Geometric parameters (Å, º) top
O1—C131.3643 (19)C8—C91.399 (2)
O1—C11.387 (2)C8—H80.9300
O2—C71.374 (2)C9—C101.479 (2)
O2—C201.407 (2)C10—C111.516 (2)
O3—C171.370 (2)C11—C121.519 (2)
O3—C211.411 (2)C11—C141.526 (2)
N1—C131.336 (2)C11—H110.9800
N1—H1A0.873 (9)C12—C131.352 (2)
N1—H1B0.861 (9)C12—C221.409 (2)
N2—C221.149 (2)C14—C151.379 (2)
C1—C101.332 (2)C14—C191.391 (2)
C1—C21.485 (2)C15—C161.383 (2)
C2—C31.514 (2)C15—H150.9300
C2—H2A0.9700C16—C171.374 (2)
C2—H2B0.9700C16—H160.9300
C3—C41.506 (3)C17—C181.381 (3)
C3—H3A0.9700C18—C191.381 (2)
C3—H3B0.9700C18—H180.9300
C4—C51.378 (2)C19—H190.9300
C4—C91.395 (2)C20—H20A0.9600
C5—C61.368 (3)C20—H20B0.9600
C5—H50.9300C20—H20C0.9600
C6—C71.378 (3)C21—H21A0.9600
C6—H60.9300C21—H21B0.9600
C7—C81.388 (2)C21—H21C0.9600
C13—O1—C1118.50 (14)C10—C11—C14111.01 (13)
C7—O2—C20119.06 (16)C12—C11—C14112.72 (13)
C17—O3—C21118.27 (16)C10—C11—H11108.1
C13—N1—H1A120.5 (13)C12—C11—H11108.1
C13—N1—H1B115.8 (14)C14—C11—H11108.1
H1A—N1—H1B123.5 (19)C13—C12—C22118.22 (16)
C10—C1—O1123.77 (15)C13—C12—C11123.09 (15)
C10—C1—C2125.35 (17)C22—C12—C11118.67 (15)
O1—C1—C2110.88 (15)N1—C13—C12128.15 (17)
C1—C2—C3110.00 (16)N1—C13—O1110.70 (16)
C1—C2—H2A109.7C12—C13—O1121.15 (16)
C3—C2—H2A109.7C15—C14—C19117.18 (16)
C1—C2—H2B109.7C15—C14—C11121.00 (15)
C3—C2—H2B109.7C19—C14—C11121.82 (16)
H2A—C2—H2B108.2C14—C15—C16122.52 (16)
C4—C3—C2112.24 (15)C14—C15—H15118.7
C4—C3—H3A109.2C16—C15—H15118.7
C2—C3—H3A109.2C17—C16—C15119.47 (17)
C4—C3—H3B109.2C17—C16—H16120.3
C2—C3—H3B109.2C15—C16—H16120.3
H3A—C3—H3B107.9O3—C17—C16124.38 (18)
C5—C4—C9118.55 (19)O3—C17—C18116.44 (17)
C5—C4—C3122.21 (18)C16—C17—C18119.18 (17)
C9—C4—C3119.21 (16)C17—C18—C19120.81 (17)
C6—C5—C4122.1 (2)C17—C18—H18119.6
C6—C5—H5119.0C19—C18—H18119.6
C4—C5—H5119.0C18—C19—C14120.79 (18)
C5—C6—C7119.9 (2)C18—C19—H19119.6
C5—C6—H6120.0C14—C19—H19119.6
C7—C6—H6120.0O2—C20—H20A109.5
O2—C7—C6116.49 (19)O2—C20—H20B109.5
O2—C7—C8124.0 (2)H20A—C20—H20B109.5
C6—C7—C8119.5 (2)O2—C20—H20C109.5
C7—C8—C9120.26 (19)H20A—C20—H20C109.5
C7—C8—H8119.9H20B—C20—H20C109.5
C9—C8—H8119.9O3—C21—H21A109.5
C4—C9—C8119.61 (17)O3—C21—H21B109.5
C4—C9—C10118.94 (17)H21A—C21—H21B109.5
C8—C9—C10121.44 (16)O3—C21—H21C109.5
C1—C10—C9118.05 (16)H21A—C21—H21C109.5
C1—C10—C11121.07 (15)H21B—C21—H21C109.5
C9—C10—C11120.87 (15)N2—C22—C12179.22 (19)
C10—C11—C12108.62 (14)
C13—O1—C1—C1010.6 (2)C1—C10—C11—C1218.5 (2)
C13—O1—C1—C2169.07 (14)C9—C10—C11—C12162.42 (14)
C10—C1—C2—C326.0 (3)C1—C10—C11—C14105.92 (18)
O1—C1—C2—C3154.25 (15)C9—C10—C11—C1473.11 (18)
C1—C2—C3—C444.3 (2)C10—C11—C12—C1318.4 (2)
C2—C3—C4—C5144.93 (18)C14—C11—C12—C13105.06 (18)
C2—C3—C4—C937.2 (2)C10—C11—C12—C22163.41 (14)
C9—C4—C5—C61.5 (3)C14—C11—C12—C2273.14 (19)
C3—C4—C5—C6176.4 (2)C22—C12—C13—N12.8 (3)
C4—C5—C6—C71.0 (3)C11—C12—C13—N1175.43 (18)
C20—O2—C7—C6173.4 (2)C22—C12—C13—O1177.10 (15)
C20—O2—C7—C88.1 (3)C11—C12—C13—O14.7 (3)
C5—C6—C7—O2179.3 (2)C1—O1—C13—N1168.94 (16)
C5—C6—C7—C82.1 (3)C1—O1—C13—C1211.0 (2)
O2—C7—C8—C9179.16 (17)C10—C11—C14—C1537.1 (2)
C6—C7—C8—C90.7 (3)C12—C11—C14—C1584.99 (19)
C5—C4—C9—C82.9 (3)C10—C11—C14—C19142.99 (16)
C3—C4—C9—C8175.08 (16)C12—C11—C14—C1994.90 (18)
C5—C4—C9—C10175.42 (16)C19—C14—C15—C160.4 (3)
C3—C4—C9—C106.6 (2)C11—C14—C15—C16179.75 (15)
C7—C8—C9—C41.8 (3)C14—C15—C16—C170.0 (3)
C7—C8—C9—C10176.47 (16)C21—O3—C17—C1614.1 (3)
O1—C1—C10—C9175.31 (14)C21—O3—C17—C18165.75 (18)
C2—C1—C10—C94.4 (3)C15—C16—C17—O3178.52 (16)
O1—C1—C10—C115.6 (3)C15—C16—C17—C181.3 (3)
C2—C1—C10—C11174.71 (15)O3—C17—C18—C19177.46 (16)
C4—C9—C10—C115.3 (2)C16—C17—C18—C192.4 (3)
C8—C9—C10—C1163.00 (16)C17—C18—C19—C142.1 (3)
C4—C9—C10—C11163.80 (15)C15—C14—C19—C180.7 (3)
C8—C9—C10—C1117.9 (2)C11—C14—C19—C18179.17 (16)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1B···O3i0.86 (1)2.20 (1)3.038 (2)165 (2)
N1—H1A···N2ii0.87 (1)2.17 (1)3.034 (2)168 (2)
Symmetry codes: (i) x+1, y, z; (ii) x+1, y, z+1.
 

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