Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807048246/hk2333sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807048246/hk2333Isup2.hkl |
CCDC reference: 667299
Key indicators
- Single-crystal X-ray study
- T = 298 K
- Mean (C-C) = 0.006 Å
- R factor = 0.074
- wR factor = 0.179
- Data-to-parameter ratio = 14.6
checkCIF/PLATON results
No syntax errors found
Alert level B PLAT230_ALERT_2_B Hirshfeld Test Diff for O2 - C20 .. 7.44 su PLAT601_ALERT_2_B Structure Contains Solvent Accessible VOIDS of . 167.00 A 3
Alert level C PLAT026_ALERT_3_C Ratio Observed / Unique Reflections too Low .... 42 Perc. PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ? PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 3.11 Ratio PLAT222_ALERT_3_C Large Non-Solvent H Ueq(max)/Ueq(min) ... 3.61 Ratio PLAT230_ALERT_2_C Hirshfeld Test Diff for N1 - C13 .. 5.56 su PLAT230_ALERT_2_C Hirshfeld Test Diff for N2 - C16 .. 6.36 su PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for O2 PLAT340_ALERT_3_C Low Bond Precision on C-C Bonds (x 1000) Ang ... 6
Alert level G PLAT793_ALERT_1_G Check the Absolute Configuration of C7 = ... S PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints ....... 6
0 ALERT level A = In general: serious problem 2 ALERT level B = Potentially serious problem 8 ALERT level C = Check and explain 2 ALERT level G = General alerts; check 2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 6 ALERT type 2 Indicator that the structure model may be wrong or deficient 4 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
For related literature, see: Hall et al. (1977); Cassady & Floss (1977); Jastrzebska-Glapa et al. (1979). For bond-length data, see: Allen et al. (1987). For ring-conformation puckering parameters, see: Cremer & Pople (1975).
The title compound, (I), was prepared by the reaction of 4-methoxybenzaldehyde (136 mg, 1 mmol), 6-aminoquinaldine (114 mg, 1 mmol) with 1,3-cyclohexanedione (112 mg, 1 mmol) in water (2 ml) at 393 K under microwave irradiation (maximum power 250 W, initial power 200 W) for 6 min (yield; 339 mg, 95%, m.p. > 573 K). Single crystals suitable for X-ray analysis were obtained from an ethanol solution (95%) by slow evaporation.
H atoms were positioned geometrically, with N—H = 0.86 (for NH) and C—H = 0.93, 0.98, 0.97 and 0.96 Å for aromatic, methine, methylene and methyl H, respectively, and constrained to ride on their parent atoms, with Uiso(H) = xUeq(C,N), where x = 1.5 for methyl H, and x = 1.2 for all other H atoms.
Compounds with the 4,7-phenanthroline motif, analogs of ergot alkaloids, possess high and versatile pharmacological effects, such as serotonin antagonism, vasoconstriction, oxytocic and psychotropic activities (Hall et al., 1977). And they are also used as inhibitors of the pituitary hormone prolactin (Cassady & Floss, 1977) and fungicides (Jastrzebska-Glapa et al., 1979). We report herein the crystal structure of the title compound, (I).
In the molecule of the title compound, (I), (Fig. 1) the bond lengths and angles are generally within normal ranges (Allen et al., 1987).
Rings A (C1—C6) and B (N1/C1/C6—C8/C13) are not planar, having total puckering amplitudes, QT, of 0.442 (2) and 0.218 (2) Å, respectively [φ = 121.08 (7)°, θ = 59.96 (5)° and φ = -7.63 (6)°, θ = 105.09 (5)°, respectively] (Cremer & Pople, 1975). Ring B has a boat conformation, while ring A adopts an envelope conformation with atom C3 displaced by 0.611 (3) Å from the plane of the other ring atoms. Rings C (C8—C13), D (N2/C9/C10/C14—C16) and E (C17—C22) are, of course, planar and the dihedral angles between them are C/D = 2.48 (3)°, C/E = 81.78 (2)° and D/E = 82.14 (2)°.
In the crystal structure, intermolecular N—H···O hydrogen bonds (Table 1) link the molecules (Fig. 2), in which they seem to be effective in the stabilization of the structure.
For related literature, see: Hall et al. (1977); Cassady & Floss (1977); Jastrzebska-Glapa et al. (1979). For bond-length data, see: Allen et al. (1987). For ring-conformation puckering parameters, see: Cremer & Pople (1975).
Data collection: SMART (Bruker, 1998); cell refinement: SAINT (Bruker, 1999); data reduction: SAINT (Bruker, 1999); 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 (Bruker, 1999).
Fig. 1. The molecular structure of the title molecule, with the atom-numbering scheme. Displacement ellipsoids are drawn at the 50% probability level. | |
Fig. 2. A packing diagram of (I). |
C23H20N2O2 | F(000) = 1504 |
Mr = 356.41 | Dx = 1.162 Mg m−3 |
Monoclinic, C2/c | Melting point > 573 K |
Hall symbol: -C 2yc | Mo Kα radiation, λ = 0.71073 Å |
a = 25.072 (3) Å | Cell parameters from 1054 reflections |
b = 7.3183 (16) Å | θ = 3.1–25.0° |
c = 23.335 (2) Å | µ = 0.08 mm−1 |
β = 107.922 (2)° | T = 298 K |
V = 4073.9 (11) Å3 | Block, yellow |
Z = 8 | 0.25 × 0.22 × 0.17 mm |
Bruker CCD area-detector diffractometer | 3561 independent reflections |
Radiation source: fine-focus sealed tube | 1506 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.091 |
φ and ω scans | θmax = 25.0°, θmin = 1.7° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −27→29 |
Tmin = 0.982, Tmax = 0.987 | k = −6→8 |
9763 measured reflections | l = −27→27 |
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.074 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.179 | H-atom parameters constrained |
S = 0.90 | w = 1/[σ2(Fo2) + (0.0682P)2] where P = (Fo2 + 2Fc2)/3 |
3561 reflections | (Δ/σ)max < 0.001 |
244 parameters | Δρmax = 0.18 e Å−3 |
6 restraints | Δρmin = −0.16 e Å−3 |
C23H20N2O2 | V = 4073.9 (11) Å3 |
Mr = 356.41 | Z = 8 |
Monoclinic, C2/c | Mo Kα radiation |
a = 25.072 (3) Å | µ = 0.08 mm−1 |
b = 7.3183 (16) Å | T = 298 K |
c = 23.335 (2) Å | 0.25 × 0.22 × 0.17 mm |
β = 107.922 (2)° |
Bruker CCD area-detector diffractometer | 3561 independent reflections |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | 1506 reflections with I > 2σ(I) |
Tmin = 0.982, Tmax = 0.987 | Rint = 0.091 |
9763 measured reflections |
R[F2 > 2σ(F2)] = 0.074 | 6 restraints |
wR(F2) = 0.179 | H-atom parameters constrained |
S = 0.90 | Δρmax = 0.18 e Å−3 |
3561 reflections | Δρmin = −0.16 e Å−3 |
244 parameters |
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. |
x | y | z | Uiso*/Ueq | ||
N1 | 0.25058 (12) | 0.2112 (4) | 0.12759 (13) | 0.0527 (8) | |
H1 | 0.2592 | 0.1025 | 0.1196 | 0.063* | |
N2 | 0.12094 (15) | 0.2715 (6) | 0.27923 (16) | 0.0776 (11) | |
O1 | 0.26478 (10) | 0.8398 (4) | 0.09987 (12) | 0.0660 (8) | |
O2 | 0.00632 (15) | 0.7318 (7) | −0.06119 (19) | 0.1331 (16) | |
C1 | 0.27071 (14) | 0.3551 (5) | 0.10386 (16) | 0.0473 (9) | |
C2 | 0.31553 (15) | 0.3166 (6) | 0.07644 (17) | 0.0587 (11) | |
H2A | 0.3072 | 0.2023 | 0.0544 | 0.070* | |
H2B | 0.3508 | 0.3016 | 0.1083 | 0.070* | |
C3 | 0.32208 (18) | 0.4638 (6) | 0.0345 (2) | 0.0752 (13) | |
H3A | 0.2910 | 0.4590 | −0.0025 | 0.090* | |
H3B | 0.3564 | 0.4443 | 0.0245 | 0.090* | |
C4 | 0.32379 (16) | 0.6511 (5) | 0.06386 (18) | 0.0629 (11) | |
H4A | 0.3596 | 0.6649 | 0.0949 | 0.076* | |
H4B | 0.3216 | 0.7445 | 0.0337 | 0.076* | |
C5 | 0.27826 (15) | 0.6826 (6) | 0.09107 (16) | 0.0519 (10) | |
C6 | 0.25135 (14) | 0.5270 (5) | 0.10778 (15) | 0.0458 (9) | |
C7 | 0.20182 (14) | 0.5607 (5) | 0.13040 (15) | 0.0489 (10) | |
H7 | 0.2102 | 0.6688 | 0.1564 | 0.059* | |
C8 | 0.19323 (14) | 0.4004 (5) | 0.16820 (15) | 0.0456 (9) | |
C9 | 0.16183 (14) | 0.4200 (5) | 0.20860 (15) | 0.0484 (10) | |
C10 | 0.15200 (16) | 0.2680 (6) | 0.24086 (17) | 0.0579 (11) | |
C11 | 0.17668 (16) | 0.0988 (6) | 0.23468 (17) | 0.0614 (11) | |
H11 | 0.1712 | −0.0021 | 0.2564 | 0.074* | |
C12 | 0.20816 (15) | 0.0827 (6) | 0.19748 (17) | 0.0558 (10) | |
H12 | 0.2243 | −0.0294 | 0.1940 | 0.067* | |
C13 | 0.21689 (14) | 0.2323 (5) | 0.16396 (15) | 0.0458 (9) | |
C14 | 0.13782 (15) | 0.5875 (6) | 0.21876 (17) | 0.0631 (11) | |
H14 | 0.1423 | 0.6927 | 0.1983 | 0.076* | |
C15 | 0.10836 (18) | 0.5925 (7) | 0.2585 (2) | 0.0820 (14) | |
H15 | 0.0934 | 0.7023 | 0.2666 | 0.098* | |
C16 | 0.1004 (2) | 0.4308 (9) | 0.2875 (2) | 0.0910 (16) | |
H16 | 0.0793 | 0.4372 | 0.3141 | 0.109* | |
C17 | 0.14855 (15) | 0.6003 (6) | 0.07851 (17) | 0.0549 (10) | |
C18 | 0.12516 (18) | 0.4690 (7) | 0.03605 (18) | 0.0704 (13) | |
H18 | 0.1413 | 0.3534 | 0.0398 | 0.084* | |
C19 | 0.07762 (19) | 0.5063 (9) | −0.0126 (2) | 0.0852 (15) | |
H19 | 0.0624 | 0.4180 | −0.0417 | 0.102* | |
C20 | 0.05397 (19) | 0.6772 (10) | −0.0163 (2) | 0.0864 (18) | |
C21 | 0.07634 (19) | 0.8092 (8) | 0.0256 (2) | 0.0856 (16) | |
H21 | 0.0597 | 0.9239 | 0.0223 | 0.103* | |
C22 | 0.12300 (17) | 0.7715 (6) | 0.07178 (19) | 0.0683 (12) | |
H22 | 0.1385 | 0.8624 | 0.0998 | 0.082* | |
C23 | −0.0179 (3) | 0.6087 (10) | −0.1060 (3) | 0.142 (2) | |
H23A | 0.0081 | 0.5787 | −0.1274 | 0.213* | |
H23B | −0.0511 | 0.6614 | −0.1335 | 0.213* | |
H23C | −0.0277 | 0.4998 | −0.0887 | 0.213* |
U11 | U22 | U33 | U12 | U13 | U23 | |
N1 | 0.070 (2) | 0.030 (2) | 0.062 (2) | 0.0002 (15) | 0.0266 (18) | 0.0000 (16) |
N2 | 0.093 (3) | 0.077 (3) | 0.073 (2) | 0.007 (2) | 0.040 (2) | 0.000 (2) |
O1 | 0.0811 (19) | 0.0320 (18) | 0.089 (2) | 0.0003 (14) | 0.0326 (16) | −0.0026 (16) |
O2 | 0.078 (3) | 0.183 (5) | 0.118 (3) | −0.016 (2) | 0.000 (2) | 0.036 (3) |
C1 | 0.048 (2) | 0.040 (3) | 0.053 (2) | −0.0018 (19) | 0.0146 (19) | −0.003 (2) |
C2 | 0.067 (3) | 0.045 (3) | 0.072 (3) | −0.0010 (19) | 0.033 (2) | −0.009 (2) |
C3 | 0.097 (3) | 0.056 (3) | 0.092 (3) | −0.005 (2) | 0.057 (3) | −0.004 (3) |
C4 | 0.080 (3) | 0.045 (3) | 0.072 (3) | −0.008 (2) | 0.034 (2) | −0.001 (2) |
C5 | 0.063 (3) | 0.039 (3) | 0.058 (2) | 0.002 (2) | 0.024 (2) | 0.000 (2) |
C6 | 0.056 (2) | 0.034 (2) | 0.053 (2) | −0.0009 (18) | 0.0246 (19) | −0.0066 (19) |
C7 | 0.055 (2) | 0.038 (2) | 0.053 (2) | −0.0003 (18) | 0.0152 (19) | −0.0037 (19) |
C8 | 0.044 (2) | 0.045 (2) | 0.047 (2) | −0.0066 (18) | 0.0126 (18) | −0.006 (2) |
C9 | 0.057 (2) | 0.045 (3) | 0.044 (2) | −0.0070 (19) | 0.0175 (19) | −0.003 (2) |
C10 | 0.061 (3) | 0.069 (3) | 0.046 (2) | −0.003 (2) | 0.020 (2) | −0.003 (2) |
C11 | 0.073 (3) | 0.053 (3) | 0.058 (2) | −0.011 (2) | 0.019 (2) | 0.009 (2) |
C12 | 0.064 (3) | 0.046 (3) | 0.059 (2) | −0.0018 (19) | 0.021 (2) | 0.000 (2) |
C13 | 0.050 (2) | 0.044 (3) | 0.048 (2) | −0.0054 (18) | 0.0223 (19) | −0.002 (2) |
C14 | 0.067 (3) | 0.061 (3) | 0.068 (3) | 0.002 (2) | 0.030 (2) | −0.007 (2) |
C15 | 0.098 (4) | 0.070 (4) | 0.092 (3) | 0.010 (3) | 0.049 (3) | −0.008 (3) |
C16 | 0.095 (4) | 0.107 (5) | 0.086 (4) | −0.010 (3) | 0.050 (3) | −0.008 (4) |
C17 | 0.051 (2) | 0.057 (3) | 0.060 (2) | 0.001 (2) | 0.023 (2) | 0.003 (2) |
C18 | 0.070 (3) | 0.074 (3) | 0.065 (3) | −0.003 (2) | 0.017 (2) | −0.005 (3) |
C19 | 0.059 (3) | 0.120 (5) | 0.069 (3) | −0.017 (3) | 0.009 (3) | 0.003 (3) |
C20 | 0.037 (3) | 0.138 (6) | 0.073 (3) | 0.000 (3) | 0.000 (2) | 0.037 (4) |
C21 | 0.050 (3) | 0.093 (4) | 0.109 (4) | 0.008 (3) | 0.017 (3) | 0.035 (4) |
C22 | 0.049 (3) | 0.071 (4) | 0.082 (3) | 0.009 (2) | 0.016 (2) | 0.011 (3) |
C23 | 0.128 (5) | 0.202 (7) | 0.090 (4) | −0.034 (4) | 0.026 (4) | 0.005 (4) |
N1—C1 | 1.357 (4) | C9—C10 | 1.407 (5) |
N1—C13 | 1.378 (4) | C9—C14 | 1.418 (5) |
N1—H1 | 0.8600 | C10—C11 | 1.411 (5) |
N2—C16 | 1.313 (6) | C11—C12 | 1.346 (5) |
N2—C10 | 1.356 (5) | C11—H11 | 0.9300 |
O1—C5 | 1.234 (4) | C12—C13 | 1.402 (5) |
O2—C23 | 1.373 (6) | C12—H12 | 0.9300 |
O2—C20 | 1.384 (5) | C14—C15 | 1.352 (5) |
C1—C6 | 1.362 (5) | C14—H14 | 0.9300 |
C1—C2 | 1.481 (5) | C15—C16 | 1.409 (6) |
C2—C3 | 1.497 (5) | C15—H15 | 0.9300 |
C2—H2A | 0.9700 | C16—H16 | 0.9300 |
C2—H2B | 0.9700 | C17—C18 | 1.375 (5) |
C3—C4 | 1.527 (5) | C17—C22 | 1.394 (5) |
C3—H3A | 0.9700 | C18—C19 | 1.397 (6) |
C3—H3B | 0.9700 | C18—H18 | 0.9300 |
C4—C5 | 1.485 (5) | C19—C20 | 1.375 (7) |
C4—H4A | 0.9700 | C19—H19 | 0.9300 |
C4—H4B | 0.9700 | C20—C21 | 1.365 (7) |
C5—C6 | 1.437 (5) | C21—C22 | 1.353 (5) |
C6—C7 | 1.512 (5) | C21—H21 | 0.9300 |
C7—C8 | 1.522 (5) | C22—H22 | 0.9300 |
C7—C17 | 1.529 (5) | C23—H23A | 0.9600 |
C7—H7 | 0.9800 | C23—H23B | 0.9600 |
C8—C13 | 1.383 (5) | C23—H23C | 0.9600 |
C8—C9 | 1.409 (5) | ||
C1—N1—C13 | 122.7 (3) | N2—C10—C9 | 124.7 (4) |
C1—N1—H1 | 118.7 | C11—C10—C9 | 119.0 (4) |
C13—N1—H1 | 118.7 | C12—C11—C10 | 120.4 (4) |
C16—N2—C10 | 116.5 (4) | C12—C11—H11 | 119.8 |
C23—O2—C20 | 117.7 (6) | C10—C11—H11 | 119.8 |
N1—C1—C6 | 120.3 (3) | C11—C12—C13 | 121.0 (4) |
N1—C1—C2 | 117.1 (3) | C11—C12—H12 | 119.5 |
C6—C1—C2 | 122.6 (4) | C13—C12—H12 | 119.5 |
C1—C2—C3 | 113.3 (3) | C8—C13—N1 | 120.1 (3) |
C1—C2—H2A | 108.9 | C8—C13—C12 | 120.7 (4) |
C3—C2—H2A | 108.9 | N1—C13—C12 | 119.1 (4) |
C1—C2—H2B | 108.9 | C15—C14—C9 | 119.2 (4) |
C3—C2—H2B | 108.9 | C15—C14—H14 | 120.4 |
H2A—C2—H2B | 107.7 | C9—C14—H14 | 120.4 |
C2—C3—C4 | 110.3 (3) | C14—C15—C16 | 119.7 (5) |
C2—C3—H3A | 109.6 | C14—C15—H15 | 120.2 |
C4—C3—H3A | 109.6 | C16—C15—H15 | 120.2 |
C2—C3—H3B | 109.6 | N2—C16—C15 | 123.7 (5) |
C4—C3—H3B | 109.6 | N2—C16—H16 | 118.1 |
H3A—C3—H3B | 108.1 | C15—C16—H16 | 118.1 |
C5—C4—C3 | 114.3 (3) | C18—C17—C22 | 117.9 (4) |
C5—C4—H4A | 108.7 | C18—C17—C7 | 120.8 (4) |
C3—C4—H4A | 108.7 | C22—C17—C7 | 121.3 (4) |
C5—C4—H4B | 108.7 | C17—C18—C19 | 121.1 (5) |
C3—C4—H4B | 108.7 | C17—C18—H18 | 119.4 |
H4A—C4—H4B | 107.6 | C19—C18—H18 | 119.4 |
O1—C5—C6 | 121.2 (3) | C20—C19—C18 | 118.2 (5) |
O1—C5—C4 | 120.1 (4) | C20—C19—H19 | 120.9 |
C6—C5—C4 | 118.7 (4) | C18—C19—H19 | 120.9 |
C1—C6—C5 | 120.5 (3) | C19—C20—C21 | 121.6 (5) |
C1—C6—C7 | 121.5 (3) | C19—C20—O2 | 124.4 (6) |
C5—C6—C7 | 118.1 (3) | C21—C20—O2 | 114.0 (6) |
C6—C7—C8 | 110.8 (3) | C22—C21—C20 | 119.3 (5) |
C6—C7—C17 | 111.4 (3) | C22—C21—H21 | 120.3 |
C8—C7—C17 | 111.1 (3) | C20—C21—H21 | 120.3 |
C6—C7—H7 | 107.8 | C21—C22—C17 | 121.8 (4) |
C8—C7—H7 | 107.8 | C21—C22—H22 | 119.1 |
C17—C7—H7 | 107.8 | C17—C22—H22 | 119.1 |
C13—C8—C9 | 118.6 (4) | O2—C23—H23A | 109.5 |
C13—C8—C7 | 120.2 (3) | O2—C23—H23B | 109.5 |
C9—C8—C7 | 121.2 (3) | H23A—C23—H23B | 109.5 |
C10—C9—C8 | 120.3 (4) | O2—C23—H23C | 109.5 |
C10—C9—C14 | 116.2 (4) | H23A—C23—H23C | 109.5 |
C8—C9—C14 | 123.6 (4) | H23B—C23—H23C | 109.5 |
N2—C10—C11 | 116.3 (4) | ||
C13—N1—C1—C6 | −10.0 (5) | C14—C9—C10—C11 | −177.4 (3) |
C13—N1—C1—C2 | 167.6 (3) | N2—C10—C11—C12 | 179.9 (3) |
N1—C1—C2—C3 | 161.1 (3) | C9—C10—C11—C12 | −1.4 (5) |
C6—C1—C2—C3 | −21.4 (5) | C10—C11—C12—C13 | −0.3 (5) |
C1—C2—C3—C4 | 47.6 (4) | C9—C8—C13—N1 | −176.2 (3) |
C2—C3—C4—C5 | −48.7 (5) | C7—C8—C13—N1 | 3.1 (5) |
C3—C4—C5—O1 | −158.6 (4) | C9—C8—C13—C12 | 2.3 (5) |
C3—C4—C5—C6 | 22.6 (5) | C7—C8—C13—C12 | −178.5 (3) |
N1—C1—C6—C5 | 170.5 (3) | C1—N1—C13—C8 | 12.8 (5) |
C2—C1—C6—C5 | −6.9 (5) | C1—N1—C13—C12 | −165.7 (3) |
N1—C1—C6—C7 | −8.6 (5) | C11—C12—C13—C8 | −0.2 (5) |
C2—C1—C6—C7 | 174.0 (3) | C11—C12—C13—N1 | 178.3 (3) |
O1—C5—C6—C1 | −172.8 (3) | C10—C9—C14—C15 | 1.0 (5) |
C4—C5—C6—C1 | 6.0 (5) | C8—C9—C14—C15 | −180.0 (3) |
O1—C5—C6—C7 | 6.4 (5) | C9—C14—C15—C16 | −2.1 (6) |
C4—C5—C6—C7 | −174.8 (3) | C10—N2—C16—C15 | 0.9 (7) |
C1—C6—C7—C8 | 21.6 (4) | C14—C15—C16—N2 | 1.2 (7) |
C5—C6—C7—C8 | −157.6 (3) | C6—C7—C17—C18 | 64.9 (4) |
C1—C6—C7—C17 | −102.7 (4) | C8—C7—C17—C18 | −59.2 (4) |
C5—C6—C7—C17 | 78.2 (4) | C6—C7—C17—C22 | −113.4 (4) |
C6—C7—C8—C13 | −18.6 (4) | C8—C7—C17—C22 | 122.5 (4) |
C17—C7—C8—C13 | 105.9 (4) | C22—C17—C18—C19 | 0.6 (6) |
C6—C7—C8—C9 | 160.6 (3) | C7—C17—C18—C19 | −177.8 (3) |
C17—C7—C8—C9 | −74.9 (4) | C17—C18—C19—C20 | −1.4 (6) |
C13—C8—C9—C10 | −4.0 (5) | C18—C19—C20—C21 | 1.1 (7) |
C7—C8—C9—C10 | 176.8 (3) | C18—C19—C20—O2 | −178.7 (4) |
C13—C8—C9—C14 | 177.0 (3) | C23—O2—C20—C19 | −2.0 (7) |
C7—C8—C9—C14 | −2.2 (5) | C23—O2—C20—C21 | 178.2 (4) |
C16—N2—C10—C11 | 176.5 (4) | C19—C20—C21—C22 | 0.1 (7) |
C16—N2—C10—C9 | −2.1 (6) | O2—C20—C21—C22 | 179.9 (4) |
C8—C9—C10—N2 | −177.8 (3) | C20—C21—C22—C17 | −1.0 (6) |
C14—C9—C10—N2 | 1.2 (5) | C18—C17—C22—C21 | 0.6 (6) |
C8—C9—C10—C11 | 3.6 (5) | C7—C17—C22—C21 | 179.0 (3) |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1···O1i | 0.86 | 1.99 | 2.842 (4) | 170 |
Symmetry code: (i) x, y−1, z. |
Experimental details
Crystal data | |
Chemical formula | C23H20N2O2 |
Mr | 356.41 |
Crystal system, space group | Monoclinic, C2/c |
Temperature (K) | 298 |
a, b, c (Å) | 25.072 (3), 7.3183 (16), 23.335 (2) |
β (°) | 107.922 (2) |
V (Å3) | 4073.9 (11) |
Z | 8 |
Radiation type | Mo Kα |
µ (mm−1) | 0.08 |
Crystal size (mm) | 0.25 × 0.22 × 0.17 |
Data collection | |
Diffractometer | Bruker CCD area-detector |
Absorption correction | Multi-scan (SADABS; Sheldrick, 1996) |
Tmin, Tmax | 0.982, 0.987 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 9763, 3561, 1506 |
Rint | 0.091 |
(sin θ/λ)max (Å−1) | 0.595 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.074, 0.179, 0.90 |
No. of reflections | 3561 |
No. of parameters | 244 |
No. of restraints | 6 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.18, −0.16 |
Computer programs: SMART (Bruker, 1998), SAINT (Bruker, 1999), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL (Bruker, 1999).
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1···O1i | 0.86 | 1.99 | 2.842 (4) | 169.6 |
Symmetry code: (i) x, y−1, z. |
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Compounds with the 4,7-phenanthroline motif, analogs of ergot alkaloids, possess high and versatile pharmacological effects, such as serotonin antagonism, vasoconstriction, oxytocic and psychotropic activities (Hall et al., 1977). And they are also used as inhibitors of the pituitary hormone prolactin (Cassady & Floss, 1977) and fungicides (Jastrzebska-Glapa et al., 1979). We report herein the crystal structure of the title compound, (I).
In the molecule of the title compound, (I), (Fig. 1) the bond lengths and angles are generally within normal ranges (Allen et al., 1987).
Rings A (C1—C6) and B (N1/C1/C6—C8/C13) are not planar, having total puckering amplitudes, QT, of 0.442 (2) and 0.218 (2) Å, respectively [φ = 121.08 (7)°, θ = 59.96 (5)° and φ = -7.63 (6)°, θ = 105.09 (5)°, respectively] (Cremer & Pople, 1975). Ring B has a boat conformation, while ring A adopts an envelope conformation with atom C3 displaced by 0.611 (3) Å from the plane of the other ring atoms. Rings C (C8—C13), D (N2/C9/C10/C14—C16) and E (C17—C22) are, of course, planar and the dihedral angles between them are C/D = 2.48 (3)°, C/E = 81.78 (2)° and D/E = 82.14 (2)°.
In the crystal structure, intermolecular N—H···O hydrogen bonds (Table 1) link the molecules (Fig. 2), in which they seem to be effective in the stabilization of the structure.