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The title compound, C
22H
19NO
3, 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
CCDC reference: 296552
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (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
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).
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.
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.
Ethyl 2-amino-4-phenyl-4
H-benzo[
h]chromene-3-carboxylate
top
Crystal data top
C22H19NO3 | F(000) = 728 |
Mr = 345.38 | Dx = 1.305 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 25 reflections |
a = 12.178 (2) Å | θ = 9–12° |
b = 8.9950 (18) Å | µ = 0.09 mm−1 |
c = 17.085 (3) Å | T = 293 K |
β = 110.03 (3)° | Block, colourless |
V = 1758.3 (6) Å3 | 0.4 × 0.3 × 0.2 mm |
Z = 4 | |
Data collection top
Enraf–Nonius CAD-4 diffractometer | Rint = 0.070 |
Radiation source: fine-focus sealed tube | θmax = 26.0°, θmin = 1.8° |
Graphite monochromator | h = 0→14 |
ω/2θ scans | k = 0→10 |
3595 measured reflections | l = −20→19 |
3431 independent reflections | 3 standard reflections every 200 reflections |
1642 reflections with I > 2σ(I) | intensity decay: <1% |
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)] = 0.066 | H-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 reflections | Δρmax = 0.41 e Å−3 |
231 parameters | Δρmin = −0.70 e Å−3 |
2 restraints | Extinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.0076 (13) |
Crystal data top
C22H19NO3 | V = 1758.3 (6) Å3 |
Mr = 345.38 | Z = 4 |
Monoclinic, P21/c | Mo Kα radiation |
a = 12.178 (2) Å | µ = 0.09 mm−1 |
b = 8.9950 (18) Å | T = 293 K |
c = 17.085 (3) Å | 0.4 × 0.3 × 0.2 mm |
β = 110.03 (3)° | |
Data collection top
Enraf–Nonius CAD-4 diffractometer | Rint = 0.070 |
3595 measured reflections | 3 standard reflections every 200 reflections |
3431 independent reflections | intensity decay: <1% |
1642 reflections with I > 2σ(I) | |
Refinement top
R[F2 > 2σ(F2)] = 0.066 | 2 restraints |
wR(F2) = 0.187 | H-atom parameters constrained |
S = 1.10 | Δρmax = 0.41 e Å−3 |
3431 reflections | Δρmin = −0.70 e Å−3 |
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 | x | y | z | Uiso*/Ueq | |
O1 | 0.8361 (2) | 0.8807 (3) | −0.04636 (16) | 0.0640 (8) | |
O2 | 0.9300 (2) | 0.6623 (3) | −0.03046 (18) | 0.0698 (9) | |
O3 | 0.7024 (2) | 0.4972 (3) | 0.08534 (15) | 0.0522 (7) | |
N1 | 0.8432 (3) | 0.4415 (4) | 0.03706 (19) | 0.0583 (9) | |
H0A | 0.8942 | 0.4589 | 0.0137 | 0.070* | |
H0B | 0.8346 | 0.3529 | 0.0529 | 0.070* | |
C1 | 0.8456 (5) | 1.0476 (7) | −0.1494 (4) | 0.134 | |
H1A | 0.8870 | 1.0734 | −0.1862 | 0.175* | |
H1B | 0.8459 | 1.1307 | −0.1141 | 0.175* | |
H1C | 0.7664 | 1.0219 | −0.1815 | 0.175* | |
C2 | 0.9017 (4) | 0.9228 (6) | −0.0990 (3) | 0.0918 (17) | |
H2A | 0.9809 | 0.9491 | −0.0649 | 0.110* | |
H2B | 0.9052 | 0.8399 | −0.1344 | 0.110* | |
C3 | 0.8555 (3) | 0.7402 (5) | −0.0175 (2) | 0.0502 (10) | |
C4 | 0.7801 (3) | 0.6971 (4) | 0.0276 (2) | 0.0423 (9) | |
C5 | 0.7774 (3) | 0.5521 (4) | 0.0488 (2) | 0.0430 (9) | |
C6 | 0.7061 (3) | 0.8130 (4) | 0.0512 (2) | 0.0430 (9) | |
H6A | 0.6691 | 0.8760 | 0.0025 | 0.052* | |
C7 | 0.7779 (3) | 0.9122 (4) | 0.1227 (2) | 0.0403 (9) | |
C8 | 0.8500 (3) | 0.8493 (4) | 0.1960 (2) | 0.0489 (10) | |
H8A | 0.8570 | 0.7463 | 0.1998 | 0.059* | |
C9 | 0.9120 (3) | 0.9347 (5) | 0.2639 (2) | 0.0557 (11) | |
H9A | 0.9600 | 0.8894 | 0.3125 | 0.067* | |
C10 | 0.9024 (3) | 1.0877 (5) | 0.2592 (3) | 0.0581 (11) | |
H10A | 0.9436 | 1.1466 | 0.3045 | 0.070* | |
C11 | 0.8313 (4) | 1.1514 (5) | 0.1866 (3) | 0.0704 (13) | |
H11A | 0.8243 | 1.2543 | 0.1830 | 0.085* | |
C12 | 0.7702 (3) | 1.0657 (5) | 0.1195 (2) | 0.0568 (11) | |
H12A | 0.7228 | 1.1116 | 0.0709 | 0.068* | |
C13 | 0.6109 (3) | 0.7379 (4) | 0.0746 (2) | 0.0414 (9) | |
C14 | 0.5176 (3) | 0.8226 (5) | 0.0840 (2) | 0.0559 (11) | |
H14A | 0.5125 | 0.9237 | 0.0719 | 0.067* | |
C15 | 0.4356 (3) | 0.7575 (6) | 0.1105 (3) | 0.0637 (12) | |
H15A | 0.3747 | 0.8148 | 0.1152 | 0.076* | |
C16 | 0.4411 (3) | 0.6053 (6) | 0.1309 (2) | 0.0580 (11) | |
C17 | 0.3603 (4) | 0.5362 (7) | 0.1625 (3) | 0.0739 (15) | |
H17A | 0.3004 | 0.5924 | 0.1697 | 0.089* | |
C18 | 0.3687 (4) | 0.3905 (7) | 0.1823 (3) | 0.0817 (16) | |
H18A | 0.3156 | 0.3482 | 0.2040 | 0.098* | |
C19 | 0.4562 (4) | 0.3026 (6) | 0.1707 (3) | 0.0759 (15) | |
H19A | 0.4600 | 0.2019 | 0.1836 | 0.091* | |
C20 | 0.5367 (3) | 0.3634 (5) | 0.1402 (2) | 0.0610 (11) | |
H20A | 0.5947 | 0.3040 | 0.1326 | 0.073* | |
C21 | 0.5316 (3) | 0.5170 (5) | 0.1202 (2) | 0.0491 (10) | |
C22 | 0.6143 (3) | 0.5908 (5) | 0.0921 (2) | 0.0445 (9) | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O1 | 0.0652 (18) | 0.078 (2) | 0.0626 (18) | 0.0024 (16) | 0.0397 (15) | 0.0154 (16) |
O2 | 0.0593 (17) | 0.087 (2) | 0.081 (2) | 0.0081 (17) | 0.0465 (16) | −0.0026 (17) |
O3 | 0.0465 (15) | 0.0556 (17) | 0.0611 (16) | 0.0085 (13) | 0.0269 (13) | 0.0081 (14) |
N1 | 0.055 (2) | 0.061 (2) | 0.068 (2) | 0.0148 (18) | 0.0324 (18) | 0.0043 (18) |
C1 | 0.140 | 0.133 | 0.183 | 0.086 | 0.123 | 0.115 |
C2 | 0.085 (3) | 0.120 (5) | 0.092 (4) | −0.003 (3) | 0.058 (3) | 0.026 (3) |
C3 | 0.046 (2) | 0.066 (3) | 0.042 (2) | −0.003 (2) | 0.0195 (18) | −0.003 (2) |
C4 | 0.0343 (19) | 0.059 (3) | 0.0363 (19) | 0.0030 (17) | 0.0158 (16) | −0.0048 (18) |
C5 | 0.037 (2) | 0.054 (3) | 0.039 (2) | 0.0048 (18) | 0.0142 (16) | −0.0022 (18) |
C6 | 0.0370 (19) | 0.057 (2) | 0.0356 (19) | 0.0089 (18) | 0.0134 (15) | 0.0083 (18) |
C7 | 0.0378 (19) | 0.047 (2) | 0.041 (2) | 0.0058 (17) | 0.0206 (16) | 0.0032 (18) |
C8 | 0.051 (2) | 0.046 (2) | 0.047 (2) | 0.0048 (19) | 0.0124 (19) | 0.0046 (19) |
C9 | 0.050 (2) | 0.064 (3) | 0.048 (2) | 0.003 (2) | 0.0105 (19) | 0.003 (2) |
C10 | 0.050 (2) | 0.066 (3) | 0.057 (3) | −0.009 (2) | 0.018 (2) | −0.009 (2) |
C11 | 0.086 (3) | 0.046 (3) | 0.081 (3) | 0.002 (2) | 0.032 (3) | −0.002 (2) |
C12 | 0.063 (3) | 0.052 (3) | 0.052 (2) | 0.006 (2) | 0.016 (2) | 0.007 (2) |
C13 | 0.0345 (19) | 0.055 (2) | 0.0336 (18) | 0.0043 (18) | 0.0102 (15) | 0.0004 (18) |
C14 | 0.044 (2) | 0.071 (3) | 0.054 (2) | 0.010 (2) | 0.0197 (19) | −0.003 (2) |
C15 | 0.040 (2) | 0.094 (4) | 0.062 (3) | 0.009 (2) | 0.024 (2) | −0.009 (3) |
C16 | 0.034 (2) | 0.100 (4) | 0.041 (2) | −0.009 (2) | 0.0138 (17) | −0.010 (2) |
C17 | 0.047 (3) | 0.120 (5) | 0.059 (3) | −0.016 (3) | 0.024 (2) | −0.014 (3) |
C18 | 0.051 (3) | 0.139 (5) | 0.061 (3) | −0.028 (3) | 0.027 (2) | −0.002 (3) |
C19 | 0.067 (3) | 0.100 (4) | 0.055 (3) | −0.033 (3) | 0.014 (2) | 0.012 (3) |
C20 | 0.053 (2) | 0.079 (3) | 0.050 (2) | −0.008 (2) | 0.017 (2) | 0.003 (2) |
C21 | 0.038 (2) | 0.075 (3) | 0.0331 (19) | −0.009 (2) | 0.0103 (16) | −0.001 (2) |
C22 | 0.0332 (19) | 0.065 (3) | 0.0358 (19) | 0.0050 (18) | 0.0122 (15) | −0.0033 (19) |
Geometric parameters (Å, º) top
O1—C3 | 1.348 (5) | C9—C10 | 1.382 (6) |
O1—C2 | 1.443 (4) | C9—H9A | 0.9300 |
O2—C3 | 1.225 (4) | C10—C11 | 1.371 (6) |
O3—C5 | 1.363 (4) | C10—H10A | 0.9300 |
O3—C22 | 1.399 (4) | C11—C12 | 1.370 (6) |
N1—C5 | 1.335 (4) | C11—H11A | 0.9300 |
N1—H0A | 0.8600 | C12—H12A | 0.9300 |
N1—H0B | 0.8600 | C13—C22 | 1.354 (5) |
C1—C2 | 1.437 (5) | C13—C14 | 1.422 (5) |
C1—H1A | 0.9600 | C14—C15 | 1.361 (5) |
C1—H1B | 0.9600 | C14—H14A | 0.9300 |
C1—H1C | 0.9600 | C15—C16 | 1.409 (6) |
C2—H2A | 0.9700 | C15—H15A | 0.9300 |
C2—H2B | 0.9700 | C16—C17 | 1.417 (6) |
C3—C4 | 1.438 (5) | C16—C21 | 1.421 (5) |
C4—C5 | 1.357 (5) | C17—C18 | 1.349 (7) |
C4—C6 | 1.520 (5) | C17—H17A | 0.9300 |
C6—C13 | 1.509 (5) | C18—C19 | 1.395 (7) |
C6—C7 | 1.524 (5) | C18—H18A | 0.9300 |
C6—H6A | 0.9800 | C19—C20 | 1.371 (5) |
C7—C8 | 1.381 (5) | C19—H19A | 0.9300 |
C7—C12 | 1.384 (5) | C20—C21 | 1.419 (6) |
C8—C9 | 1.380 (5) | C20—H20A | 0.9300 |
C8—H8A | 0.9300 | C21—C22 | 1.420 (5) |
| | | |
C3—O1—C2 | 114.1 (3) | C10—C9—H9A | 120.2 |
C5—O3—C22 | 118.2 (3) | C11—C10—C9 | 118.9 (4) |
C5—N1—H0A | 120.0 | C11—C10—H10A | 120.5 |
C5—N1—H0B | 120.0 | C9—C10—H10A | 120.5 |
H0A—N1—H0B | 120.0 | C12—C11—C10 | 121.1 (4) |
C2—C1—H1A | 109.5 | C12—C11—H11A | 119.5 |
C2—C1—H1B | 109.5 | C10—C11—H11A | 119.5 |
H1A—C1—H1B | 109.5 | C11—C12—C7 | 121.1 (4) |
C2—C1—H1C | 109.5 | C11—C12—H12A | 119.4 |
H1A—C1—H1C | 109.5 | C7—C12—H12A | 119.4 |
H1B—C1—H1C | 109.5 | C22—C13—C14 | 117.6 (3) |
C1—C2—O1 | 109.1 (4) | C22—C13—C6 | 121.8 (3) |
C1—C2—H2A | 109.9 | C14—C13—C6 | 120.4 (3) |
O1—C2—H2A | 109.9 | C15—C14—C13 | 120.8 (4) |
C1—C2—H2B | 109.9 | C15—C14—H14A | 119.6 |
O1—C2—H2B | 109.9 | C13—C14—H14A | 119.6 |
H2A—C2—H2B | 108.3 | C14—C15—C16 | 121.5 (4) |
O2—C3—O1 | 121.2 (4) | C14—C15—H15A | 119.2 |
O2—C3—C4 | 126.2 (4) | C16—C15—H15A | 119.2 |
O1—C3—C4 | 112.6 (3) | C15—C16—C17 | 122.8 (4) |
C5—C4—C3 | 118.7 (3) | C15—C16—C21 | 118.9 (4) |
C5—C4—C6 | 121.1 (3) | C17—C16—C21 | 118.3 (5) |
C3—C4—C6 | 120.2 (3) | C18—C17—C16 | 121.3 (5) |
N1—C5—C4 | 127.3 (3) | C18—C17—H17A | 119.3 |
N1—C5—O3 | 109.2 (3) | C16—C17—H17A | 119.3 |
C4—C5—O3 | 123.5 (3) | C17—C18—C19 | 120.7 (5) |
C13—C6—C4 | 110.1 (3) | C17—C18—H18A | 119.7 |
C13—C6—C7 | 109.4 (3) | C19—C18—H18A | 119.7 |
C4—C6—C7 | 112.6 (3) | C20—C19—C18 | 120.6 (5) |
C13—C6—H6A | 108.2 | C20—C19—H19A | 119.7 |
C4—C6—H6A | 108.2 | C18—C19—H19A | 119.7 |
C7—C6—H6A | 108.2 | C19—C20—C21 | 120.1 (4) |
C8—C7—C12 | 117.3 (4) | C19—C20—H20A | 119.9 |
C8—C7—C6 | 120.0 (3) | C21—C20—H20A | 119.9 |
C12—C7—C6 | 122.7 (3) | C20—C21—C22 | 124.0 (4) |
C9—C8—C7 | 121.9 (4) | C20—C21—C16 | 119.0 (4) |
C9—C8—H8A | 119.0 | C22—C21—C16 | 117.0 (4) |
C7—C8—H8A | 119.0 | C13—C22—O3 | 122.4 (3) |
C8—C9—C10 | 119.7 (4) | C13—C22—C21 | 124.0 (4) |
C8—C9—H9A | 120.2 | O3—C22—C21 | 113.5 (3) |
| | | |
C3—O1—C2—C1 | 159.1 (5) | C7—C6—C13—C22 | −108.5 (4) |
C2—O1—C3—O2 | 5.7 (5) | C4—C6—C13—C14 | −168.2 (3) |
C2—O1—C3—C4 | −174.1 (3) | C7—C6—C13—C14 | 67.5 (4) |
O2—C3—C4—C5 | −9.8 (6) | C22—C13—C14—C15 | 0.6 (5) |
O1—C3—C4—C5 | 169.9 (3) | C6—C13—C14—C15 | −175.5 (3) |
O2—C3—C4—C6 | 169.7 (4) | C13—C14—C15—C16 | 1.2 (6) |
O1—C3—C4—C6 | −10.6 (5) | C14—C15—C16—C17 | 176.8 (4) |
C3—C4—C5—N1 | 4.4 (6) | C14—C15—C16—C21 | −2.6 (6) |
C6—C4—C5—N1 | −175.1 (3) | C15—C16—C17—C18 | −179.2 (4) |
C3—C4—C5—O3 | −174.4 (3) | C21—C16—C17—C18 | 0.2 (6) |
C6—C4—C5—O3 | 6.1 (5) | C16—C17—C18—C19 | −1.3 (7) |
C22—O3—C5—N1 | −171.0 (3) | C17—C18—C19—C20 | 1.2 (7) |
C22—O3—C5—C4 | 8.1 (5) | C18—C19—C20—C21 | 0.0 (6) |
C5—C4—C6—C13 | −17.0 (5) | C19—C20—C21—C22 | 176.9 (3) |
C3—C4—C6—C13 | 163.5 (3) | C19—C20—C21—C16 | −1.1 (5) |
C5—C4—C6—C7 | 105.4 (4) | C15—C16—C21—C20 | −179.6 (4) |
C3—C4—C6—C7 | −74.1 (4) | C17—C16—C21—C20 | 1.0 (5) |
C13—C6—C7—C8 | 69.8 (4) | C15—C16—C21—C22 | 2.3 (5) |
C4—C6—C7—C8 | −52.9 (4) | C17—C16—C21—C22 | −177.2 (3) |
C13—C6—C7—C12 | −106.9 (4) | C14—C13—C22—O3 | −179.7 (3) |
C4—C6—C7—C12 | 130.4 (4) | C6—C13—C22—O3 | −3.6 (5) |
C12—C7—C8—C9 | 0.3 (5) | C14—C13—C22—C21 | −0.8 (5) |
C6—C7—C8—C9 | −176.6 (3) | C6—C13—C22—C21 | 175.2 (3) |
C7—C8—C9—C10 | 0.0 (6) | C5—O3—C22—C13 | −9.4 (5) |
C8—C9—C10—C11 | −0.1 (6) | C5—O3—C22—C21 | 171.7 (3) |
C9—C10—C11—C12 | −0.1 (6) | C20—C21—C22—C13 | −178.7 (4) |
C10—C11—C12—C7 | 0.3 (6) | C16—C21—C22—C13 | −0.6 (5) |
C8—C7—C12—C11 | −0.4 (6) | C20—C21—C22—O3 | 0.3 (5) |
C6—C7—C12—C11 | 176.4 (3) | C16—C21—C22—O3 | 178.4 (3) |
C4—C6—C13—C22 | 15.8 (5) | | |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H0A···O2 | 0.86 | 2.08 | 2.688 (4) | 127 |
N1—H0A···O2i | 0.86 | 2.33 | 2.954 (4) | 130 |
Symmetry code: (i) −x+2, −y+1, −z. |
Experimental details
Crystal data |
Chemical formula | C22H19NO3 |
Mr | 345.38 |
Crystal system, space group | Monoclinic, P21/c |
Temperature (K) | 293 |
a, b, c (Å) | 12.178 (2), 8.9950 (18), 17.085 (3) |
β (°) | 110.03 (3) |
V (Å3) | 1758.3 (6) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.09 |
Crystal size (mm) | 0.4 × 0.3 × 0.2 |
|
Data collection |
Diffractometer | Enraf–Nonius CAD-4 diffractometer |
Absorption correction | – |
No. of measured, independent and observed [I > 2σ(I)] reflections | 3595, 3431, 1642 |
Rint | 0.070 |
(sin θ/λ)max (Å−1) | 0.616 |
|
Refinement |
R[F2 > 2σ(F2)], wR(F2), S | 0.066, 0.187, 1.10 |
No. of reflections | 3431 |
No. of parameters | 231 |
No. of restraints | 2 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.41, −0.70 |
Selected geometric parameters (Å, º) topO1—C3 | 1.348 (5) | N1—C5 | 1.335 (4) |
O1—C2 | 1.443 (4) | C1—C2 | 1.437 (5) |
O2—C3 | 1.225 (4) | C3—C4 | 1.438 (5) |
O3—C5 | 1.363 (4) | C6—C7 | 1.524 (5) |
O3—C22 | 1.399 (4) | | |
| | | |
C3—O1—C2 | 114.1 (3) | C4—C5—O3 | 123.5 (3) |
C5—O3—C22 | 118.2 (3) | C13—C6—C7 | 109.4 (3) |
C1—C2—O1 | 109.1 (4) | C4—C6—C7 | 112.6 (3) |
O2—C3—O1 | 121.2 (4) | C8—C7—C6 | 120.0 (3) |
O2—C3—C4 | 126.2 (4) | C12—C7—C6 | 122.7 (3) |
O1—C3—C4 | 112.6 (3) | C14—C13—C6 | 120.4 (3) |
C5—C4—C3 | 118.7 (3) | C20—C21—C22 | 124.0 (4) |
C3—C4—C6 | 120.2 (3) | C13—C22—O3 | 122.4 (3) |
N1—C5—C4 | 127.3 (3) | O3—C22—C21 | 113.5 (3) |
N1—C5—O3 | 109.2 (3) | | |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H0A···O2 | 0.86 | 2.08 | 2.688 (4) | 127 |
N1—H0A···O2i | 0.86 | 2.33 | 2.954 (4) | 130 |
Symmetry code: (i) −x+2, −y+1, −z. |
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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.