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The title compound, C22H18N2O4, was synthesized by the reaction of 7-methoxy-2-tetralone and 3,4-methylenedioxybenzylidenemalononitrile 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 screw-boat forms, respectively.
Supporting information
CCDC reference: 262454
Key indicators
- Single-crystal X-ray study
- T = 299 K
- Mean (C-C) = 0.002 Å
- R factor = 0.035
- wR factor = 0.082
- Data-to-parameter ratio = 13.1
checkCIF/PLATON results
No syntax errors found
Alert level B
PLAT230_ALERT_2_B Hirshfeld Test Diff for C12 - C22 .. 8.79 su
Alert level C
PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 2.87 Ratio
PLAT230_ALERT_2_C Hirshfeld Test Diff for C8 - C9 .. 6.11 su
PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... # 68
C13 -C12 -C22 -N1 138.00 13.00 1.555 1.555 1.555 1.555
PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... # 69
C11 -C12 -C22 -N1 -44.00 13.00 1.555 1.555 1.555 1.555
0 ALERT level A = In general: serious problem
1 ALERT level B = Potentially serious problem
4 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
3 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
2 ALERT type 4 Improvement, methodology, query or suggestion
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: SHELXTL; software used to prepare material for publication: SHELXTL.
3-Amino-1-(3,4-methylenedioxyphenyl)-9-methoxy-5,6-dihydro-1
H-
benzo[
f]chromene-2-carbonitrile
top
Crystal data top
C22H18N2O4 | F(000) = 784 |
Mr = 374.38 | Dx = 1.349 Mg m−3 |
Monoclinic, P21/c | Melting point = 502–504 K |
Hall symbol: -P 2ybc | Mo Kα radiation, λ = 0.71073 Å |
a = 10.277 (1) Å | Cell parameters from 34 reflections |
b = 6.9852 (5) Å | θ = 5.6–13.2° |
c = 25.695 (3) Å | µ = 0.09 mm−1 |
β = 92.512 (9)° | T = 299 K |
V = 1842.8 (3) Å3 | Block, colorless |
Z = 4 | 0.56 × 0.38 × 0.24 mm |
Data collection top
Siemens P4 diffractometer | Rint = 0.011 |
Radiation source: normal-focus sealed tube | θmax = 25.3°, θmin = 1.6° |
Graphite monochromator | h = 0→12 |
ω scans | k = 0→8 |
3993 measured reflections | l = −30→30 |
3336 independent reflections | 3 standard reflections every 97 reflections |
2127 reflections with I > 2σ(I) | intensity decay: 4.2% |
Refinement top
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.035 | H-atom parameters constrained |
wR(F2) = 0.082 | w = 1/[σ2(Fo2) + (0.0419P)2] where P = (Fo2 + 2Fc2)/3 |
S = 0.86 | (Δ/σ)max < 0.001 |
3336 reflections | Δρmax = 0.15 e Å−3 |
255 parameters | Δρmin = −0.12 e Å−3 |
0 restraints | Extinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.0121 (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 | x | y | z | Uiso*/Ueq | |
O1 | 0.56034 (10) | 0.41831 (15) | 0.41235 (4) | 0.0465 (3) | |
O2 | −0.14994 (10) | 0.37739 (18) | 0.45876 (5) | 0.0557 (3) | |
O3 | 0.01292 (11) | 0.15261 (17) | 0.45358 (5) | 0.0556 (4) | |
O4 | 0.11119 (14) | 0.5291 (2) | 0.18618 (5) | 0.0825 (5) | |
N1 | 0.37050 (14) | 1.0042 (2) | 0.46110 (6) | 0.0570 (4) | |
N2 | 0.61707 (13) | 0.6404 (2) | 0.47042 (5) | 0.0530 (4) | |
H20A | 0.6085 | 0.7463 | 0.4870 | 0.064* | |
H20B | 0.6830 | 0.5676 | 0.4775 | 0.064* | |
C1 | 0.49146 (15) | 0.3574 (2) | 0.36761 (6) | 0.0379 (4) | |
C2 | 0.55403 (16) | 0.1867 (2) | 0.34515 (7) | 0.0471 (4) | |
H2A | 0.5898 | 0.1061 | 0.3730 | 0.056* | |
H2B | 0.6250 | 0.2267 | 0.3240 | 0.056* | |
C3 | 0.45527 (18) | 0.0747 (2) | 0.31212 (7) | 0.0526 (5) | |
H3A | 0.5008 | −0.0146 | 0.2905 | 0.063* | |
H3B | 0.4012 | 0.0010 | 0.3348 | 0.063* | |
C4 | 0.36961 (17) | 0.2008 (2) | 0.27789 (6) | 0.0454 (4) | |
C5 | 0.3239 (2) | 0.1447 (3) | 0.22867 (7) | 0.0630 (6) | |
H5 | 0.3512 | 0.0282 | 0.2154 | 0.076* | |
C6 | 0.2395 (2) | 0.2559 (3) | 0.19897 (8) | 0.0696 (6) | |
H6 | 0.2114 | 0.2153 | 0.1659 | 0.084* | |
C7 | 0.19654 (18) | 0.4272 (3) | 0.21809 (7) | 0.0557 (5) | |
C8 | 0.24169 (15) | 0.4893 (3) | 0.26707 (6) | 0.0459 (4) | |
H8 | 0.2131 | 0.6055 | 0.2801 | 0.055* | |
C9 | 0.32992 (15) | 0.3777 (2) | 0.29684 (6) | 0.0375 (4) | |
C10 | 0.38564 (15) | 0.4454 (2) | 0.34771 (6) | 0.0338 (4) | |
C11 | 0.32353 (14) | 0.6093 (2) | 0.37555 (5) | 0.0332 (4) | |
H11 | 0.3077 | 0.7122 | 0.3501 | 0.040* | |
C12 | 0.41888 (14) | 0.6846 (2) | 0.41745 (6) | 0.0339 (4) | |
C13 | 0.52743 (15) | 0.5888 (2) | 0.43344 (6) | 0.0375 (4) | |
C14 | 0.19213 (14) | 0.5536 (2) | 0.39694 (5) | 0.0324 (4) | |
C15 | 0.09305 (16) | 0.6861 (2) | 0.39950 (6) | 0.0442 (4) | |
H15 | 0.1064 | 0.8093 | 0.3871 | 0.053* | |
C16 | −0.02645 (16) | 0.6412 (3) | 0.42019 (6) | 0.0485 (5) | |
H16 | −0.0919 | 0.7323 | 0.4226 | 0.058* | |
C17 | −0.04278 (15) | 0.4586 (2) | 0.43662 (6) | 0.0402 (4) | |
C18 | −0.12318 (17) | 0.1774 (3) | 0.46057 (8) | 0.0608 (5) | |
H18A | −0.1735 | 0.1116 | 0.4332 | 0.073* | |
H18B | −0.1464 | 0.1249 | 0.4939 | 0.073* | |
C19 | 0.05449 (15) | 0.3242 (2) | 0.43385 (6) | 0.0362 (4) | |
C20 | 0.17263 (14) | 0.3668 (2) | 0.41509 (6) | 0.0349 (4) | |
H20 | 0.2383 | 0.2753 | 0.4143 | 0.042* | |
C21 | 0.0506 (2) | 0.6920 (4) | 0.20610 (8) | 0.0927 (8) | |
H21A | 0.0093 | 0.6590 | 0.2377 | 0.111* | |
H21B | −0.0137 | 0.7386 | 0.1810 | 0.111* | |
H21C | 0.1146 | 0.7896 | 0.2132 | 0.111* | |
C22 | 0.39242 (15) | 0.8605 (2) | 0.44185 (6) | 0.0385 (4) | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O1 | 0.0471 (7) | 0.0381 (7) | 0.0535 (7) | 0.0103 (6) | −0.0070 (6) | −0.0106 (6) |
O2 | 0.0341 (7) | 0.0606 (9) | 0.0732 (8) | 0.0057 (6) | 0.0124 (6) | −0.0018 (7) |
O3 | 0.0421 (7) | 0.0474 (8) | 0.0788 (9) | 0.0027 (6) | 0.0202 (6) | 0.0115 (7) |
O4 | 0.0798 (10) | 0.1126 (13) | 0.0530 (8) | 0.0154 (10) | −0.0208 (8) | −0.0142 (9) |
N1 | 0.0554 (10) | 0.0467 (10) | 0.0672 (10) | 0.0145 (8) | −0.0140 (8) | −0.0188 (9) |
N2 | 0.0439 (8) | 0.0511 (9) | 0.0626 (10) | 0.0133 (8) | −0.0144 (7) | −0.0178 (8) |
C1 | 0.0408 (9) | 0.0348 (9) | 0.0384 (9) | −0.0021 (8) | 0.0070 (8) | −0.0039 (8) |
C2 | 0.0500 (10) | 0.0366 (10) | 0.0555 (11) | 0.0061 (9) | 0.0131 (9) | −0.0031 (8) |
C3 | 0.0694 (12) | 0.0341 (10) | 0.0554 (11) | −0.0009 (10) | 0.0172 (10) | −0.0085 (9) |
C4 | 0.0545 (11) | 0.0411 (10) | 0.0415 (10) | −0.0083 (9) | 0.0121 (8) | −0.0088 (8) |
C5 | 0.0747 (14) | 0.0582 (13) | 0.0567 (12) | −0.0055 (12) | 0.0102 (11) | −0.0245 (11) |
C6 | 0.0754 (15) | 0.0855 (16) | 0.0475 (12) | −0.0082 (13) | −0.0033 (11) | −0.0261 (12) |
C7 | 0.0520 (12) | 0.0724 (14) | 0.0422 (10) | −0.0075 (11) | −0.0022 (9) | −0.0067 (10) |
C8 | 0.0482 (10) | 0.0502 (11) | 0.0395 (10) | −0.0053 (9) | 0.0050 (8) | −0.0075 (8) |
C9 | 0.0407 (9) | 0.0379 (9) | 0.0344 (8) | −0.0057 (8) | 0.0087 (7) | −0.0032 (8) |
C10 | 0.0388 (9) | 0.0303 (8) | 0.0329 (8) | −0.0034 (8) | 0.0084 (7) | −0.0010 (7) |
C11 | 0.0390 (9) | 0.0287 (8) | 0.0315 (8) | 0.0019 (7) | −0.0004 (7) | 0.0014 (7) |
C12 | 0.0370 (9) | 0.0283 (9) | 0.0365 (9) | 0.0034 (7) | 0.0014 (7) | −0.0019 (7) |
C13 | 0.0396 (9) | 0.0326 (9) | 0.0402 (9) | 0.0018 (8) | 0.0019 (8) | −0.0046 (8) |
C14 | 0.0333 (9) | 0.0333 (9) | 0.0300 (8) | 0.0051 (7) | −0.0029 (7) | −0.0021 (7) |
C15 | 0.0458 (10) | 0.0347 (10) | 0.0518 (10) | 0.0091 (8) | −0.0015 (8) | 0.0022 (8) |
C16 | 0.0379 (10) | 0.0485 (11) | 0.0590 (11) | 0.0188 (9) | −0.0002 (8) | −0.0037 (9) |
C17 | 0.0298 (9) | 0.0499 (11) | 0.0409 (9) | 0.0053 (9) | 0.0002 (7) | −0.0048 (8) |
C18 | 0.0427 (11) | 0.0625 (14) | 0.0781 (14) | −0.0016 (10) | 0.0134 (10) | −0.0004 (11) |
C19 | 0.0350 (9) | 0.0369 (10) | 0.0367 (9) | 0.0033 (8) | 0.0019 (7) | 0.0000 (7) |
C20 | 0.0329 (8) | 0.0338 (9) | 0.0380 (9) | 0.0102 (7) | 0.0012 (7) | −0.0007 (8) |
C21 | 0.0877 (17) | 0.119 (2) | 0.0695 (15) | 0.0338 (17) | −0.0200 (13) | −0.0035 (15) |
C22 | 0.0353 (9) | 0.0392 (10) | 0.0404 (9) | 0.0030 (8) | −0.0060 (7) | −0.0008 (8) |
Geometric parameters (Å, º) top
O1—C13 | 1.3572 (17) | C6—H6 | 0.9300 |
O1—C1 | 1.3902 (18) | C7—C8 | 1.392 (2) |
O2—C17 | 1.3830 (19) | C8—C9 | 1.398 (2) |
O2—C18 | 1.424 (2) | C8—H8 | 0.9300 |
O3—C19 | 1.3768 (18) | C9—C10 | 1.481 (2) |
O3—C18 | 1.4286 (19) | C10—C11 | 1.5066 (19) |
O4—C7 | 1.373 (2) | C11—C12 | 1.518 (2) |
O4—C21 | 1.405 (2) | C11—C14 | 1.530 (2) |
N1—C22 | 1.1459 (19) | C11—H11 | 0.9800 |
N2—C13 | 1.3434 (18) | C12—C13 | 1.350 (2) |
N2—H20A | 0.8600 | C12—C22 | 1.411 (2) |
N2—H20B | 0.8600 | C14—C15 | 1.380 (2) |
C1—C10 | 1.332 (2) | C14—C20 | 1.403 (2) |
C1—C2 | 1.483 (2) | C15—C16 | 1.395 (2) |
C2—C3 | 1.512 (2) | C15—H15 | 0.9300 |
C2—H2A | 0.9700 | C16—C17 | 1.357 (2) |
C2—H2B | 0.9700 | C16—H16 | 0.9300 |
C3—C4 | 1.502 (2) | C17—C19 | 1.375 (2) |
C3—H3A | 0.9700 | C18—H18A | 0.9700 |
C3—H3B | 0.9700 | C18—H18B | 0.9700 |
C4—C5 | 1.387 (2) | C19—C20 | 1.359 (2) |
C4—C9 | 1.395 (2) | C20—H20 | 0.9300 |
C5—C6 | 1.370 (3) | C21—H21A | 0.9600 |
C5—H5 | 0.9300 | C21—H21B | 0.9600 |
C6—C7 | 1.374 (3) | C21—H21C | 0.9600 |
| | | |
C13—O1—C1 | 118.17 (13) | C10—C11—C12 | 109.06 (12) |
C17—O2—C18 | 105.04 (13) | C10—C11—C14 | 112.10 (12) |
C19—O3—C18 | 105.19 (12) | C12—C11—C14 | 112.70 (12) |
C7—O4—C21 | 118.97 (15) | C10—C11—H11 | 107.6 |
C13—N2—H20A | 120.0 | C12—C11—H11 | 107.6 |
C13—N2—H20B | 120.0 | C14—C11—H11 | 107.6 |
H20A—N2—H20B | 120.0 | C13—C12—C22 | 118.00 (14) |
C10—C1—O1 | 123.63 (14) | C13—C12—C11 | 122.91 (13) |
C10—C1—C2 | 125.61 (15) | C22—C12—C11 | 119.07 (13) |
O1—C1—C2 | 110.74 (13) | N2—C13—C12 | 127.89 (15) |
C1—C2—C3 | 110.03 (14) | N2—C13—O1 | 110.05 (14) |
C1—C2—H2A | 109.7 | C12—C13—O1 | 122.06 (14) |
C3—C2—H2A | 109.7 | C15—C14—C20 | 119.46 (14) |
C1—C2—H2B | 109.7 | C15—C14—C11 | 120.74 (14) |
C3—C2—H2B | 109.7 | C20—C14—C11 | 119.80 (13) |
H2A—C2—H2B | 108.2 | C14—C15—C16 | 122.07 (16) |
C4—C3—C2 | 112.74 (14) | C14—C15—H15 | 119.0 |
C4—C3—H3A | 109.0 | C16—C15—H15 | 119.0 |
C2—C3—H3A | 109.0 | C17—C16—C15 | 116.94 (16) |
C4—C3—H3B | 109.0 | C17—C16—H16 | 121.5 |
C2—C3—H3B | 109.0 | C15—C16—H16 | 121.5 |
H3A—C3—H3B | 107.8 | C16—C17—C19 | 121.70 (16) |
C5—C4—C9 | 118.44 (17) | C16—C17—O2 | 128.70 (15) |
C5—C4—C3 | 122.32 (16) | C19—C17—O2 | 109.59 (14) |
C9—C4—C3 | 119.19 (15) | O2—C18—O3 | 107.67 (14) |
C6—C5—C4 | 121.89 (18) | O2—C18—H18A | 110.2 |
C6—C5—H5 | 119.1 | O3—C18—H18A | 110.2 |
C4—C5—H5 | 119.1 | O2—C18—H18B | 110.2 |
C5—C6—C7 | 120.00 (18) | O3—C18—H18B | 110.2 |
C5—C6—H6 | 120.0 | H18A—C18—H18B | 108.5 |
C7—C6—H6 | 120.0 | C20—C19—C17 | 122.14 (15) |
O4—C7—C6 | 116.43 (17) | C20—C19—O3 | 128.14 (14) |
O4—C7—C8 | 123.87 (18) | C17—C19—O3 | 109.70 (13) |
C6—C7—C8 | 119.69 (19) | C19—C20—C14 | 117.66 (14) |
C7—C8—C9 | 120.23 (17) | C19—C20—H20 | 121.2 |
C7—C8—H8 | 119.9 | C14—C20—H20 | 121.2 |
C9—C8—H8 | 119.9 | O4—C21—H21A | 109.5 |
C4—C9—C8 | 119.69 (15) | O4—C21—H21B | 109.5 |
C4—C9—C10 | 118.88 (15) | H21A—C21—H21B | 109.5 |
C8—C9—C10 | 121.41 (14) | O4—C21—H21C | 109.5 |
C1—C10—C9 | 117.97 (14) | H21A—C21—H21C | 109.5 |
C1—C10—C11 | 121.62 (14) | H21B—C21—H21C | 109.5 |
C9—C10—C11 | 120.41 (13) | N1—C22—C12 | 179.19 (18) |
| | | |
C13—O1—C1—C10 | −8.0 (2) | C14—C11—C12—C13 | 111.63 (16) |
C13—O1—C1—C2 | 170.51 (13) | C10—C11—C12—C22 | 167.91 (13) |
C10—C1—C2—C3 | −24.9 (2) | C14—C11—C12—C22 | −66.92 (17) |
O1—C1—C2—C3 | 156.55 (14) | C22—C12—C13—N2 | −0.5 (2) |
C1—C2—C3—C4 | 43.47 (19) | C11—C12—C13—N2 | −179.07 (15) |
C2—C3—C4—C5 | 145.71 (16) | C22—C12—C13—O1 | 179.73 (13) |
C2—C3—C4—C9 | −37.0 (2) | C11—C12—C13—O1 | 1.2 (2) |
C9—C4—C5—C6 | −1.3 (3) | C1—O1—C13—N2 | −169.32 (13) |
C3—C4—C5—C6 | 176.03 (18) | C1—O1—C13—C12 | 10.5 (2) |
C4—C5—C6—C7 | −0.9 (3) | C10—C11—C14—C15 | −147.15 (14) |
C21—O4—C7—C6 | 171.61 (19) | C12—C11—C14—C15 | 89.36 (16) |
C21—O4—C7—C8 | −9.5 (3) | C10—C11—C14—C20 | 34.06 (18) |
C5—C6—C7—O4 | −179.33 (18) | C12—C11—C14—C20 | −89.43 (16) |
C5—C6—C7—C8 | 1.7 (3) | C20—C14—C15—C16 | 0.7 (2) |
O4—C7—C8—C9 | −179.19 (16) | C11—C14—C15—C16 | −178.10 (14) |
C6—C7—C8—C9 | −0.3 (3) | C14—C15—C16—C17 | −1.7 (2) |
C5—C4—C9—C8 | 2.7 (2) | C15—C16—C17—C19 | 1.0 (2) |
C3—C4—C9—C8 | −174.75 (15) | C15—C16—C17—O2 | 179.47 (15) |
C5—C4—C9—C10 | −175.60 (15) | C18—O2—C17—C16 | 170.82 (18) |
C3—C4—C9—C10 | 7.0 (2) | C18—O2—C17—C19 | −10.57 (18) |
C7—C8—C9—C4 | −1.9 (2) | C17—O2—C18—O3 | 16.46 (19) |
C7—C8—C9—C10 | 176.31 (14) | C19—O3—C18—O2 | −16.18 (19) |
O1—C1—C10—C9 | 173.62 (13) | C16—C17—C19—C20 | 0.7 (3) |
C2—C1—C10—C9 | −4.7 (2) | O2—C17—C19—C20 | −178.02 (13) |
O1—C1—C10—C11 | −6.3 (2) | C16—C17—C19—O3 | 179.26 (15) |
C2—C1—C10—C11 | 175.41 (14) | O2—C17—C19—O3 | 0.54 (18) |
C4—C9—C10—C1 | 14.8 (2) | C18—O3—C19—C20 | −171.84 (16) |
C8—C9—C10—C1 | −163.41 (15) | C18—O3—C19—C17 | 9.71 (18) |
C4—C9—C10—C11 | −165.27 (14) | C17—C19—C20—C14 | −1.7 (2) |
C8—C9—C10—C11 | 16.5 (2) | O3—C19—C20—C14 | −179.99 (14) |
C1—C10—C11—C12 | 15.81 (19) | C15—C14—C20—C19 | 1.0 (2) |
C9—C10—C11—C12 | −164.08 (13) | C11—C14—C20—C19 | 179.82 (13) |
C1—C10—C11—C14 | −109.70 (16) | C13—C12—C22—N1 | 138 (13) |
C9—C10—C11—C14 | 70.41 (16) | C11—C12—C22—N1 | −44 (13) |
C10—C11—C12—C13 | −13.54 (19) | | |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N2—H20A···N1i | 0.86 | 2.20 | 3.042 (2) | 167 |
N2—H20B···O2ii | 0.86 | 2.24 | 3.043 (2) | 155 |
Symmetry codes: (i) −x+1, −y+2, −z+1; (ii) x+1, y, z. |
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