In the monoclinic crystalline phase, the molecules of the title compound, C
21H
15NO
2, form columns extending along the [001] direction. The crystals are stabilized by π–π stacking interactions, formed between acridine systems, and C—H
π hydrogen-bond contacts, in which benzene rings are involved. The layers, resulting in the C—H
π hydrogen-bond contacts, formed between acridine H atoms and benzene rings of neighboring columns, are parallel to the (100) plane. C—H
N hydrogen bonds between layers stabilize the crystal structure. All the acridine rings are parallel in the crystal structure, while the benzene rings are either parallel or inclined at 52.8 (2)°. The acridine systems and benzene rings in the molecules are inclined at 30.0 (2)° to each other, and the acridine systems and carboxylate groups at 58.0 (3)°.
Supporting information
CCDC reference: 298361
Key indicators
- Single-crystal X-ray study
- T = 100 K
- Mean (C-C) = 0.007 Å
- R factor = 0.067
- wR factor = 0.192
- Data-to-parameter ratio = 11.7
checkCIF/PLATON results
No syntax errors found
Alert level B
PLAT029_ALERT_3_B _diffrn_measured_fraction_theta_full Low ....... 0.94
Alert level C
REFLT03_ALERT_3_C Reflection count < 95% complete
From the CIF: _diffrn_reflns_theta_max 25.00
From the CIF: _diffrn_reflns_theta_full 25.00
From the CIF: _reflns_number_total 2551
TEST2: Reflns within _diffrn_reflns_theta_max
Count of symmetry unique reflns 2717
Completeness (_total/calc) 93.89%
PLAT022_ALERT_3_C Ratio Unique / Expected Reflections too Low .... 0.94
PLAT026_ALERT_3_C Ratio Observed / Unique Reflections too Low .... 42 Perc.
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 7
PLAT480_ALERT_4_C Long H...A H-Bond Reported H7 .. CG4 .. 2.91 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H23 .. CG4 .. 2.90 Ang.
0 ALERT level A = In general: serious problem
1 ALERT level B = Potentially serious problem
6 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
0 ALERT type 2 Indicator that the structure model may be wrong or deficient
5 ALERT type 3 Indicator that the structure quality may be low
2 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: CrysAlis CCD (Oxford Diffraction, 2003); cell refinement: CrysAlis RED (Oxford Diffraction, 2003); data reduction: CrysAlis RED; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPII (Johnson, 1976); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2003).
2-Methylphenyl acridine-9-carboxylate
top
Crystal data top
C21H15NO2 | F(000) = 656 |
Mr = 313.34 | Dx = 1.348 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 5975 reflections |
a = 12.376 (5) Å | θ = 3.1–25.0° |
b = 17.725 (6) Å | µ = 0.09 mm−1 |
c = 7.100 (3) Å | T = 100 K |
β = 97.42 (3)° | Needle, pale yellow |
V = 1544.4 (10) Å3 | 0.3 × 0.1 × 0.1 mm |
Z = 4 | |
Data collection top
Kuma KM4 CCD κ-geometry diffractometer | 1064 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.073 |
Graphite monochromator | θmax = 25.0°, θmin = 3.1° |
ω scans | h = −14→14 |
5572 measured reflections | k = −13→21 |
2551 independent reflections | l = −8→6 |
Refinement top
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)] = 0.067 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.192 | H-atom parameters constrained |
S = 1.00 | w = 1/[σ2(Fo2) + (0.075P)2] where P = (Fo2 + 2Fc2)/3 |
2551 reflections | (Δ/σ)max < 0.001 |
218 parameters | Δρmax = 0.38 e Å−3 |
0 restraints | Δρmin = −0.26 e Å−3 |
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. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
C1 | 0.6808 (4) | 0.2941 (3) | 0.1660 (7) | 0.0257 (13) | |
H1 | 0.6055 | 0.2975 | 0.1194 | 0.031* | |
C2 | 0.7390 (4) | 0.3581 (3) | 0.2032 (7) | 0.0293 (13) | |
H2 | 0.7038 | 0.4057 | 0.1854 | 0.035* | |
C3 | 0.8532 (4) | 0.3549 (3) | 0.2692 (7) | 0.0267 (13) | |
H3 | 0.8939 | 0.4001 | 0.2928 | 0.032* | |
C4 | 0.9030 (4) | 0.2867 (3) | 0.2977 (7) | 0.0246 (13) | |
H4 | 0.9785 | 0.2852 | 0.3440 | 0.029* | |
C5 | 0.9080 (4) | 0.0197 (3) | 0.2885 (7) | 0.0298 (14) | |
H5 | 0.9838 | 0.0216 | 0.3328 | 0.036* | |
C6 | 0.8581 (4) | −0.0479 (3) | 0.2585 (7) | 0.0308 (14) | |
H6 | 0.8999 | −0.0928 | 0.2802 | 0.037* | |
C7 | 0.7441 (4) | −0.0536 (3) | 0.1948 (7) | 0.0285 (13) | |
H7 | 0.7103 | −0.1016 | 0.1764 | 0.034* | |
C8 | 0.6849 (4) | 0.0102 (3) | 0.1610 (7) | 0.0227 (13) | |
H8 | 0.6092 | 0.0060 | 0.1179 | 0.027* | |
C9 | 0.6754 (3) | 0.1527 (3) | 0.1620 (7) | 0.0204 (12) | |
N10 | 0.9012 (3) | 0.1528 (2) | 0.2915 (5) | 0.0250 (10) | |
C11 | 0.7300 (4) | 0.2215 (3) | 0.1954 (7) | 0.0222 (13) | |
C12 | 0.8462 (4) | 0.2181 (3) | 0.2608 (7) | 0.0244 (13) | |
C13 | 0.7321 (4) | 0.0841 (3) | 0.1879 (7) | 0.0184 (12) | |
C14 | 0.8481 (4) | 0.0879 (3) | 0.2542 (7) | 0.0233 (13) | |
C15 | 0.5557 (4) | 0.1498 (3) | 0.0981 (7) | 0.0223 (12) | |
O16 | 0.4994 (3) | 0.18560 (17) | 0.2254 (5) | 0.0269 (9) | |
O17 | 0.5111 (2) | 0.11903 (18) | −0.0418 (5) | 0.0281 (9) | |
C18 | 0.3851 (4) | 0.1779 (3) | 0.1985 (7) | 0.0240 (13) | |
C19 | 0.3399 (4) | 0.1145 (3) | 0.2734 (7) | 0.0248 (13) | |
C20 | 0.2273 (4) | 0.1102 (3) | 0.2579 (7) | 0.0332 (14) | |
H20 | 0.1942 | 0.0668 | 0.3041 | 0.040* | |
C21 | 0.1624 (4) | 0.1682 (3) | 0.1762 (8) | 0.0360 (15) | |
H21 | 0.0853 | 0.1644 | 0.1676 | 0.043* | |
C22 | 0.2091 (4) | 0.2317 (3) | 0.1069 (7) | 0.0321 (14) | |
H22 | 0.1642 | 0.2714 | 0.0516 | 0.039* | |
C23 | 0.3227 (4) | 0.2374 (3) | 0.1183 (8) | 0.0307 (14) | |
H23 | 0.3560 | 0.2808 | 0.0724 | 0.037* | |
C24 | 0.4107 (4) | 0.0529 (3) | 0.3676 (8) | 0.0352 (15) | |
H24C | 0.4760 | 0.0751 | 0.4391 | 0.053* | |
H24B | 0.4321 | 0.0186 | 0.2706 | 0.053* | |
H24A | 0.3702 | 0.0248 | 0.4544 | 0.053* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
C1 | 0.022 (3) | 0.031 (3) | 0.025 (4) | 0.001 (3) | 0.010 (2) | 0.003 (3) |
C2 | 0.034 (3) | 0.020 (3) | 0.033 (4) | −0.005 (3) | 0.004 (3) | −0.001 (3) |
C3 | 0.033 (3) | 0.020 (3) | 0.027 (3) | −0.007 (3) | 0.003 (3) | −0.009 (2) |
C4 | 0.020 (3) | 0.035 (3) | 0.021 (3) | −0.005 (3) | 0.012 (2) | −0.005 (3) |
C5 | 0.021 (3) | 0.031 (3) | 0.038 (4) | 0.003 (3) | 0.009 (3) | 0.003 (3) |
C6 | 0.030 (3) | 0.025 (3) | 0.039 (4) | 0.005 (3) | 0.009 (3) | 0.004 (3) |
C7 | 0.022 (3) | 0.031 (3) | 0.034 (4) | −0.004 (3) | 0.009 (3) | −0.005 (3) |
C8 | 0.017 (3) | 0.034 (3) | 0.019 (3) | −0.005 (2) | 0.008 (2) | 0.001 (2) |
C9 | 0.012 (2) | 0.033 (3) | 0.017 (3) | −0.001 (2) | 0.007 (2) | −0.001 (3) |
N10 | 0.027 (2) | 0.029 (2) | 0.021 (3) | 0.001 (2) | 0.0074 (19) | 0.003 (2) |
C11 | 0.020 (3) | 0.029 (3) | 0.019 (3) | 0.004 (2) | 0.004 (2) | −0.001 (3) |
C12 | 0.033 (3) | 0.021 (3) | 0.019 (3) | −0.007 (3) | 0.005 (3) | −0.007 (2) |
C13 | 0.015 (3) | 0.025 (3) | 0.016 (3) | −0.002 (2) | 0.004 (2) | −0.007 (2) |
C14 | 0.023 (3) | 0.028 (3) | 0.019 (3) | 0.001 (3) | 0.001 (2) | −0.005 (2) |
C15 | 0.024 (3) | 0.022 (3) | 0.022 (3) | −0.003 (2) | 0.008 (2) | −0.001 (3) |
O16 | 0.0226 (19) | 0.029 (2) | 0.030 (2) | −0.0035 (16) | 0.0076 (17) | −0.0079 (17) |
O17 | 0.0197 (18) | 0.036 (2) | 0.028 (2) | 0.0006 (16) | 0.0011 (16) | −0.0069 (19) |
C18 | 0.011 (3) | 0.038 (3) | 0.022 (3) | −0.001 (2) | 0.000 (2) | −0.006 (3) |
C19 | 0.029 (3) | 0.025 (3) | 0.022 (3) | −0.002 (3) | 0.009 (2) | −0.002 (3) |
C20 | 0.030 (3) | 0.034 (3) | 0.037 (4) | −0.010 (3) | 0.009 (3) | −0.003 (3) |
C21 | 0.027 (3) | 0.047 (4) | 0.033 (4) | 0.005 (3) | −0.002 (3) | −0.006 (3) |
C22 | 0.027 (3) | 0.046 (4) | 0.025 (4) | 0.015 (3) | 0.011 (3) | 0.003 (3) |
C23 | 0.029 (3) | 0.032 (3) | 0.030 (4) | 0.007 (3) | −0.002 (3) | 0.002 (3) |
C24 | 0.034 (3) | 0.029 (3) | 0.043 (4) | 0.002 (3) | 0.007 (3) | 0.001 (3) |
Geometric parameters (Å, º) top
C1—C2 | 1.352 (6) | N10—C14 | 1.334 (6) |
C1—C11 | 1.427 (6) | N10—C12 | 1.347 (6) |
C1—H1 | 0.9500 | C11—C12 | 1.454 (6) |
C2—C3 | 1.431 (6) | C13—C14 | 1.454 (6) |
C2—H2 | 0.9500 | C15—O16 | 1.366 (5) |
C3—C4 | 1.361 (6) | C15—O17 | 1.203 (5) |
C3—H3 | 0.9500 | O16—C18 | 1.409 (5) |
C4—C12 | 1.413 (6) | C18—C23 | 1.385 (6) |
C4—H4 | 0.9500 | C18—C19 | 1.392 (6) |
C5—C6 | 1.352 (6) | C19—C20 | 1.386 (6) |
C5—C14 | 1.423 (6) | C19—C24 | 1.502 (6) |
C5—H5 | 0.9500 | C20—C21 | 1.385 (7) |
C6—C7 | 1.429 (6) | C20—H20 | 0.9500 |
C6—H6 | 0.9500 | C21—C22 | 1.385 (7) |
C7—C8 | 1.351 (6) | C21—H21 | 0.9500 |
C7—H7 | 0.9500 | C22—C23 | 1.401 (6) |
C8—C13 | 1.438 (6) | C22—H22 | 0.9500 |
C8—H8 | 0.9500 | C23—H23 | 0.9500 |
C9—C11 | 1.400 (6) | C24—H24C | 0.9800 |
C9—C13 | 1.403 (6) | C24—H24B | 0.9800 |
C9—C15 | 1.494 (6) | C24—H24A | 0.9800 |
| | | |
C2—C1—C11 | 121.4 (5) | C9—C13—C8 | 125.8 (4) |
C2—C1—H1 | 119.3 | C9—C13—C14 | 117.3 (4) |
C11—C1—H1 | 119.3 | C8—C13—C14 | 116.9 (4) |
C1—C2—C3 | 120.6 (5) | N10—C14—C5 | 117.8 (4) |
C1—C2—H2 | 119.7 | N10—C14—C13 | 123.0 (4) |
C3—C2—H2 | 119.7 | C5—C14—C13 | 119.2 (5) |
C4—C3—C2 | 119.6 (5) | O17—C15—O16 | 122.5 (4) |
C4—C3—H3 | 120.2 | C9—C15—O16 | 110.8 (4) |
C2—C3—H3 | 120.2 | C9—C15—O17 | 126.7 (5) |
C3—C4—C12 | 122.1 (5) | C15—O16—C18 | 117.0 (4) |
C3—C4—H4 | 118.9 | C23—C18—C19 | 122.8 (4) |
C12—C4—H4 | 118.9 | C23—C18—O16 | 118.6 (5) |
C6—C5—C14 | 120.6 (5) | C19—C18—O16 | 118.2 (4) |
C6—C5—H5 | 119.7 | C20—C19—C18 | 117.6 (5) |
C14—C5—H5 | 119.7 | C20—C19—C24 | 121.2 (5) |
C5—C6—C7 | 121.6 (5) | C18—C19—C24 | 121.2 (4) |
C5—C6—H6 | 119.2 | C21—C20—C19 | 121.1 (5) |
C7—C6—H6 | 119.2 | C21—C20—H20 | 119.5 |
C8—C7—C6 | 119.2 (5) | C19—C20—H20 | 119.5 |
C8—C7—H7 | 120.4 | C22—C21—C20 | 120.3 (5) |
C6—C7—H7 | 120.4 | C22—C21—H21 | 119.8 |
C7—C8—C13 | 122.5 (5) | C20—C21—H21 | 119.8 |
C7—C8—H8 | 118.8 | C21—C22—C23 | 120.0 (5) |
C13—C8—H8 | 118.8 | C21—C22—H22 | 120.0 |
C11—C9—C13 | 120.7 (4) | C23—C22—H22 | 120.0 |
C11—C9—C15 | 121.2 (5) | C18—C23—C22 | 118.1 (5) |
C13—C9—C15 | 118.0 (4) | C18—C23—H23 | 121.0 |
C14—N10—C12 | 118.9 (4) | C22—C23—H23 | 121.0 |
C9—C11—C1 | 125.0 (4) | C19—C24—H24C | 109.5 |
C9—C11—C12 | 116.9 (4) | C19—C24—H24B | 109.5 |
C1—C11—C12 | 118.0 (5) | H24C—C24—H24B | 109.5 |
N10—C12—C4 | 118.7 (5) | C19—C24—H24A | 109.5 |
N10—C12—C11 | 123.1 (4) | H24C—C24—H24A | 109.5 |
C4—C12—C11 | 118.2 (5) | H24B—C24—H24A | 109.5 |
| | | |
C11—C1—C2—C3 | 1.6 (8) | C12—N10—C14—C13 | −2.2 (7) |
C1—C2—C3—C4 | −1.2 (8) | C6—C5—C14—N10 | 178.2 (5) |
C2—C3—C4—C12 | 1.3 (8) | C6—C5—C14—C13 | 0.5 (8) |
C14—C5—C6—C7 | −1.0 (8) | C9—C13—C14—N10 | 0.4 (7) |
C5—C6—C7—C8 | 1.0 (8) | C8—C13—C14—N10 | −177.5 (5) |
C6—C7—C8—C13 | −0.4 (8) | C9—C13—C14—C5 | 177.9 (5) |
C13—C9—C11—C1 | 177.4 (5) | C8—C13—C14—C5 | 0.0 (7) |
C15—C9—C11—C1 | −2.7 (8) | C11—C9—C15—O17 | 124.2 (6) |
C13—C9—C11—C12 | −1.1 (7) | C13—C9—C15—O17 | −55.9 (7) |
C15—C9—C11—C12 | 178.8 (4) | C11—C9—C15—O16 | −57.9 (6) |
C2—C1—C11—C9 | 179.4 (5) | C13—C9—C15—O16 | 122.0 (5) |
C2—C1—C11—C12 | −2.1 (7) | O17—C15—O16—C18 | 7.0 (7) |
C14—N10—C12—C4 | −179.1 (5) | C9—C15—O16—C18 | −170.9 (4) |
C14—N10—C12—C11 | 2.4 (7) | C15—O16—C18—C23 | −102.5 (5) |
C3—C4—C12—N10 | 179.6 (5) | C15—O16—C18—C19 | 84.7 (5) |
C3—C4—C12—C11 | −1.8 (7) | C23—C18—C19—C20 | 3.0 (7) |
C9—C11—C12—N10 | −0.8 (7) | O16—C18—C19—C20 | 175.5 (4) |
C1—C11—C12—N10 | −179.4 (5) | C23—C18—C19—C24 | −177.0 (5) |
C9—C11—C12—C4 | −179.3 (5) | O16—C18—C19—C24 | −4.5 (7) |
C1—C11—C12—C4 | 2.1 (7) | C18—C19—C20—C21 | −2.0 (8) |
C11—C9—C13—C8 | 179.0 (5) | C24—C19—C20—C21 | 178.0 (5) |
C15—C9—C13—C8 | −0.9 (7) | C19—C20—C21—C22 | 0.4 (8) |
C11—C9—C13—C14 | 1.3 (7) | C20—C21—C22—C23 | 0.3 (8) |
C15—C9—C13—C14 | −178.6 (4) | C19—C18—C23—C22 | −2.3 (8) |
C7—C8—C13—C9 | −177.8 (5) | O16—C18—C23—C22 | −174.7 (4) |
C7—C8—C13—C14 | −0.1 (8) | C21—C22—C23—C18 | 0.6 (8) |
C12—N10—C14—C5 | −179.8 (5) | | |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C21—H21···N10i | 0.95 | 2.55 | 3.446 (6) | 156 |
C7—H7···Cg4ii | 0.95 | 2.91 | 3.435 (6) | 116 |
C23—H23···Cg4iii | 0.95 | 2.90 | 3.421 (6) | 116 |
Symmetry codes: (i) x−1, y, z; (ii) −x+1, −y, −z; (iii) x, −y−1/2, z−3/2. |
π–π interactions (Å, °) in (I). Cg represents the centroids of
the rings, as follows: Cg1 ring C9/C11/C12/N10/C14/C13 and Cg2 ring
C1/C2/C3/C4/C12/C11. topCgI | CgJ | Cg···Cg | Dihedral angle | Interplanar dist. | Offset |
1 | 2iii | 3.656 (3) | 2.0 | 3.431 (3) | 1.262 (2) |
1 | 2iv | 3.739 (3) | 2.0 | 3.519 (3) | 1.264 (2) |
2 | 1iii | 3.739 (3) | 2.0 | 3.490 (3) | 1.342 (2) |
2 | 1iv | 3.656 (3) | 2.0 | 3.470 (3) | 1.151 (2) |
2 | 2iii | 3.809 (3) | 1.1 | 3.489 (3) | 1.528 (2) |
2 | 2iv | 3.809 (3) | 1.1 | 3.461 (3) | 1.591 (2) |
Cg···Cg is the distance between ring centroids.
The dihedral angle is that between the planes of the rings CgI and CgJ.
The interplanar distance is the perpendicular distance of CgI from ring J.
The offset is the perpendicular distance of ring I from ring J.
Symmetry codes: (iii) x, -1/2-y, z-3/2; (iv) x, 1/2-y, 1/2+z. |