Download citation
Download citation
link to html
In the monoclinic crystalline phase, the mol­ecules of the title compound, C21H15NO2, 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

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806000377/at6072sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806000377/at6072Isup2.hkl
Contains datablock I

CCDC reference: 298361

Key indicators

  • Single-crystal X-ray study
  • T = 100 K
  • Mean [sigma](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

Computing details top

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
C21H15NO2F(000) = 656
Mr = 313.34Dx = 1.348 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 5975 reflections
a = 12.376 (5) Åθ = 3.1–25.0°
b = 17.725 (6) ŵ = 0.09 mm1
c = 7.100 (3) ÅT = 100 K
β = 97.42 (3)°Needle, pale yellow
V = 1544.4 (10) Å30.3 × 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 tubeRint = 0.073
Graphite monochromatorθmax = 25.0°, θmin = 3.1°
ω scansh = 1414
5572 measured reflectionsk = 1321
2551 independent reflectionsl = 86
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.067Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.192H-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 parametersΔρmax = 0.38 e Å3
0 restraintsΔρmin = 0.26 e Å3
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
xyzUiso*/Ueq
C10.6808 (4)0.2941 (3)0.1660 (7)0.0257 (13)
H10.60550.29750.11940.031*
C20.7390 (4)0.3581 (3)0.2032 (7)0.0293 (13)
H20.70380.40570.18540.035*
C30.8532 (4)0.3549 (3)0.2692 (7)0.0267 (13)
H30.89390.40010.29280.032*
C40.9030 (4)0.2867 (3)0.2977 (7)0.0246 (13)
H40.97850.28520.34400.029*
C50.9080 (4)0.0197 (3)0.2885 (7)0.0298 (14)
H50.98380.02160.33280.036*
C60.8581 (4)0.0479 (3)0.2585 (7)0.0308 (14)
H60.89990.09280.28020.037*
C70.7441 (4)0.0536 (3)0.1948 (7)0.0285 (13)
H70.71030.10160.17640.034*
C80.6849 (4)0.0102 (3)0.1610 (7)0.0227 (13)
H80.60920.00600.11790.027*
C90.6754 (3)0.1527 (3)0.1620 (7)0.0204 (12)
N100.9012 (3)0.1528 (2)0.2915 (5)0.0250 (10)
C110.7300 (4)0.2215 (3)0.1954 (7)0.0222 (13)
C120.8462 (4)0.2181 (3)0.2608 (7)0.0244 (13)
C130.7321 (4)0.0841 (3)0.1879 (7)0.0184 (12)
C140.8481 (4)0.0879 (3)0.2542 (7)0.0233 (13)
C150.5557 (4)0.1498 (3)0.0981 (7)0.0223 (12)
O160.4994 (3)0.18560 (17)0.2254 (5)0.0269 (9)
O170.5111 (2)0.11903 (18)0.0418 (5)0.0281 (9)
C180.3851 (4)0.1779 (3)0.1985 (7)0.0240 (13)
C190.3399 (4)0.1145 (3)0.2734 (7)0.0248 (13)
C200.2273 (4)0.1102 (3)0.2579 (7)0.0332 (14)
H200.19420.06680.30410.040*
C210.1624 (4)0.1682 (3)0.1762 (8)0.0360 (15)
H210.08530.16440.16760.043*
C220.2091 (4)0.2317 (3)0.1069 (7)0.0321 (14)
H220.16420.27140.05160.039*
C230.3227 (4)0.2374 (3)0.1183 (8)0.0307 (14)
H230.35600.28080.07240.037*
C240.4107 (4)0.0529 (3)0.3676 (8)0.0352 (15)
H24C0.47600.07510.43910.053*
H24B0.43210.01860.27060.053*
H24A0.37020.02480.45440.053*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.022 (3)0.031 (3)0.025 (4)0.001 (3)0.010 (2)0.003 (3)
C20.034 (3)0.020 (3)0.033 (4)0.005 (3)0.004 (3)0.001 (3)
C30.033 (3)0.020 (3)0.027 (3)0.007 (3)0.003 (3)0.009 (2)
C40.020 (3)0.035 (3)0.021 (3)0.005 (3)0.012 (2)0.005 (3)
C50.021 (3)0.031 (3)0.038 (4)0.003 (3)0.009 (3)0.003 (3)
C60.030 (3)0.025 (3)0.039 (4)0.005 (3)0.009 (3)0.004 (3)
C70.022 (3)0.031 (3)0.034 (4)0.004 (3)0.009 (3)0.005 (3)
C80.017 (3)0.034 (3)0.019 (3)0.005 (2)0.008 (2)0.001 (2)
C90.012 (2)0.033 (3)0.017 (3)0.001 (2)0.007 (2)0.001 (3)
N100.027 (2)0.029 (2)0.021 (3)0.001 (2)0.0074 (19)0.003 (2)
C110.020 (3)0.029 (3)0.019 (3)0.004 (2)0.004 (2)0.001 (3)
C120.033 (3)0.021 (3)0.019 (3)0.007 (3)0.005 (3)0.007 (2)
C130.015 (3)0.025 (3)0.016 (3)0.002 (2)0.004 (2)0.007 (2)
C140.023 (3)0.028 (3)0.019 (3)0.001 (3)0.001 (2)0.005 (2)
C150.024 (3)0.022 (3)0.022 (3)0.003 (2)0.008 (2)0.001 (3)
O160.0226 (19)0.029 (2)0.030 (2)0.0035 (16)0.0076 (17)0.0079 (17)
O170.0197 (18)0.036 (2)0.028 (2)0.0006 (16)0.0011 (16)0.0069 (19)
C180.011 (3)0.038 (3)0.022 (3)0.001 (2)0.000 (2)0.006 (3)
C190.029 (3)0.025 (3)0.022 (3)0.002 (3)0.009 (2)0.002 (3)
C200.030 (3)0.034 (3)0.037 (4)0.010 (3)0.009 (3)0.003 (3)
C210.027 (3)0.047 (4)0.033 (4)0.005 (3)0.002 (3)0.006 (3)
C220.027 (3)0.046 (4)0.025 (4)0.015 (3)0.011 (3)0.003 (3)
C230.029 (3)0.032 (3)0.030 (4)0.007 (3)0.002 (3)0.002 (3)
C240.034 (3)0.029 (3)0.043 (4)0.002 (3)0.007 (3)0.001 (3)
Geometric parameters (Å, º) top
C1—C21.352 (6)N10—C141.334 (6)
C1—C111.427 (6)N10—C121.347 (6)
C1—H10.9500C11—C121.454 (6)
C2—C31.431 (6)C13—C141.454 (6)
C2—H20.9500C15—O161.366 (5)
C3—C41.361 (6)C15—O171.203 (5)
C3—H30.9500O16—C181.409 (5)
C4—C121.413 (6)C18—C231.385 (6)
C4—H40.9500C18—C191.392 (6)
C5—C61.352 (6)C19—C201.386 (6)
C5—C141.423 (6)C19—C241.502 (6)
C5—H50.9500C20—C211.385 (7)
C6—C71.429 (6)C20—H200.9500
C6—H60.9500C21—C221.385 (7)
C7—C81.351 (6)C21—H210.9500
C7—H70.9500C22—C231.401 (6)
C8—C131.438 (6)C22—H220.9500
C8—H80.9500C23—H230.9500
C9—C111.400 (6)C24—H24C0.9800
C9—C131.403 (6)C24—H24B0.9800
C9—C151.494 (6)C24—H24A0.9800
C2—C1—C11121.4 (5)C9—C13—C8125.8 (4)
C2—C1—H1119.3C9—C13—C14117.3 (4)
C11—C1—H1119.3C8—C13—C14116.9 (4)
C1—C2—C3120.6 (5)N10—C14—C5117.8 (4)
C1—C2—H2119.7N10—C14—C13123.0 (4)
C3—C2—H2119.7C5—C14—C13119.2 (5)
C4—C3—C2119.6 (5)O17—C15—O16122.5 (4)
C4—C3—H3120.2C9—C15—O16110.8 (4)
C2—C3—H3120.2C9—C15—O17126.7 (5)
C3—C4—C12122.1 (5)C15—O16—C18117.0 (4)
C3—C4—H4118.9C23—C18—C19122.8 (4)
C12—C4—H4118.9C23—C18—O16118.6 (5)
C6—C5—C14120.6 (5)C19—C18—O16118.2 (4)
C6—C5—H5119.7C20—C19—C18117.6 (5)
C14—C5—H5119.7C20—C19—C24121.2 (5)
C5—C6—C7121.6 (5)C18—C19—C24121.2 (4)
C5—C6—H6119.2C21—C20—C19121.1 (5)
C7—C6—H6119.2C21—C20—H20119.5
C8—C7—C6119.2 (5)C19—C20—H20119.5
C8—C7—H7120.4C22—C21—C20120.3 (5)
C6—C7—H7120.4C22—C21—H21119.8
C7—C8—C13122.5 (5)C20—C21—H21119.8
C7—C8—H8118.8C21—C22—C23120.0 (5)
C13—C8—H8118.8C21—C22—H22120.0
C11—C9—C13120.7 (4)C23—C22—H22120.0
C11—C9—C15121.2 (5)C18—C23—C22118.1 (5)
C13—C9—C15118.0 (4)C18—C23—H23121.0
C14—N10—C12118.9 (4)C22—C23—H23121.0
C9—C11—C1125.0 (4)C19—C24—H24C109.5
C9—C11—C12116.9 (4)C19—C24—H24B109.5
C1—C11—C12118.0 (5)H24C—C24—H24B109.5
N10—C12—C4118.7 (5)C19—C24—H24A109.5
N10—C12—C11123.1 (4)H24C—C24—H24A109.5
C4—C12—C11118.2 (5)H24B—C24—H24A109.5
C11—C1—C2—C31.6 (8)C12—N10—C14—C132.2 (7)
C1—C2—C3—C41.2 (8)C6—C5—C14—N10178.2 (5)
C2—C3—C4—C121.3 (8)C6—C5—C14—C130.5 (8)
C14—C5—C6—C71.0 (8)C9—C13—C14—N100.4 (7)
C5—C6—C7—C81.0 (8)C8—C13—C14—N10177.5 (5)
C6—C7—C8—C130.4 (8)C9—C13—C14—C5177.9 (5)
C13—C9—C11—C1177.4 (5)C8—C13—C14—C50.0 (7)
C15—C9—C11—C12.7 (8)C11—C9—C15—O17124.2 (6)
C13—C9—C11—C121.1 (7)C13—C9—C15—O1755.9 (7)
C15—C9—C11—C12178.8 (4)C11—C9—C15—O1657.9 (6)
C2—C1—C11—C9179.4 (5)C13—C9—C15—O16122.0 (5)
C2—C1—C11—C122.1 (7)O17—C15—O16—C187.0 (7)
C14—N10—C12—C4179.1 (5)C9—C15—O16—C18170.9 (4)
C14—N10—C12—C112.4 (7)C15—O16—C18—C23102.5 (5)
C3—C4—C12—N10179.6 (5)C15—O16—C18—C1984.7 (5)
C3—C4—C12—C111.8 (7)C23—C18—C19—C203.0 (7)
C9—C11—C12—N100.8 (7)O16—C18—C19—C20175.5 (4)
C1—C11—C12—N10179.4 (5)C23—C18—C19—C24177.0 (5)
C9—C11—C12—C4179.3 (5)O16—C18—C19—C244.5 (7)
C1—C11—C12—C42.1 (7)C18—C19—C20—C212.0 (8)
C11—C9—C13—C8179.0 (5)C24—C19—C20—C21178.0 (5)
C15—C9—C13—C80.9 (7)C19—C20—C21—C220.4 (8)
C11—C9—C13—C141.3 (7)C20—C21—C22—C230.3 (8)
C15—C9—C13—C14178.6 (4)C19—C18—C23—C222.3 (8)
C7—C8—C13—C9177.8 (5)O16—C18—C23—C22174.7 (4)
C7—C8—C13—C140.1 (8)C21—C22—C23—C180.6 (8)
C12—N10—C14—C5179.8 (5)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C21—H21···N10i0.952.553.446 (6)156
C7—H7···Cg4ii0.952.913.435 (6)116
C23—H23···Cg4iii0.952.903.421 (6)116
Symmetry codes: (i) x1, y, z; (ii) x+1, y, z; (iii) x, y1/2, z3/2.
ππ 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. top
CgICgJCg···CgDihedral angleInterplanar dist.Offset
12iii3.656 (3)2.03.431 (3)1.262 (2)
12iv3.739 (3)2.03.519 (3)1.264 (2)
21iii3.739 (3)2.03.490 (3)1.342 (2)
21iv3.656 (3)2.03.470 (3)1.151 (2)
22iii3.809 (3)1.13.489 (3)1.528 (2)
22iv3.809 (3)1.13.461 (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.
 

Follow Acta Cryst. E
Sign up for e-alerts
Follow Acta Cryst. on Twitter
Follow us on facebook
Sign up for RSS feeds