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The title compound, C24H19ClN2O, consists of a carbazole skeleton with ethyl and 4-chloroquinoline-N-aldehyde substit­uents. The di­hydro­pyridine ring adopts a half-chair conform­ation. The molecular packing is stabilized by C—Cl...π interactions.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536803020130/bt6352sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536803020130/bt6352Isup2.hkl
Contains datablock I

CCDC reference: 225790

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.003 Å
  • R factor = 0.049
  • wR factor = 0.141
  • Data-to-parameter ratio = 15.0

checkCIF/PLATON results

No syntax errors found



Alert level A PLAT029_ALERT_3_A _diffrn_measured_fraction_theta_full Low ....... 0.90
Alert level B REFLT03_ALERT_3_B Reflection count < 90% complete (theta max?) From the CIF: _diffrn_reflns_theta_max 28.01 From the CIF: _diffrn_reflns_theta_full 0.00 From the CIF: _reflns_number_total 4119 TEST2: Reflns within _diffrn_reflns_theta_max Count of symmetry unique reflns 4583 Completeness (_total/calc) 89.88%
Alert level C PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 2.57 Ratio PLAT222_ALERT_3_C Large Non-Solvent H Ueq(max)/Ueq(min) ... 3.21 Ratio PLAT242_ALERT_2_C Check Low U(eq) as Compared to Neighbors .... C9B PLAT301_ALERT_3_C Main Residue Disorder ......................... 7.00 Perc.
1 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 2 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

Computing details top

Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ZORTEP (Zsolnai, 1997) and PLATON (Spek, 1990); software used to prepare material for publication: SHELXL97 and PARST (Nardelli, 1995).

C-halogen···π interaction: 4-Chloro-2-(9-ethylcarbazol-3-yl)quinoline-1(2H)- carbaldehyde. top
Crystal data top
C24H19ClN2OZ = 2
Mr = 386.86F(000) = 404
Triclinic, P1Dx = 1.356 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 9.4147 (8) ÅCell parameters from 2301 reflections
b = 9.6714 (8) Åθ = 2.3–27.3°
c = 11.1245 (9) ŵ = 0.22 mm1
α = 85.336 (1)°T = 293 K
β = 70.235 (1)°Needle, colourless
γ = 84.351 (2)°0.24 × 0.18 × 0.12 mm
V = 947.37 (14) Å3
Data collection top
Siemens SMART CCD area detector
diffractometer
3187 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.017
Graphite monochromatorθmax = 28.0°, θmin = 2.0°
ω scansh = 1111
5918 measured reflectionsk = 1212
4119 independent reflectionsl = 149
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)] = 0.049Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.141H-atom parameters constrained
S = 1.01 w = 1/[σ2(Fo2) + (0.0818P)2 + 0.0963P]
where P = (Fo2 + 2Fc2)/3
4119 reflections(Δ/σ)max = 0.001
274 parametersΔρmax = 0.28 e Å3
0 restraintsΔρmin = 0.16 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.

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
xyzUiso*/UeqOcc. (<1)
Cl10.09873 (7)1.12653 (5)0.15707 (5)0.0698 (2)
O10.43464 (15)0.58798 (15)0.15635 (13)0.0670 (4)
N10.11123 (19)0.34051 (19)0.40043 (18)0.0683 (5)
C10.1116 (2)0.5125 (2)0.2187 (2)0.0587 (5)
H10.21020.50160.22280.070*
C1A0.0486 (2)0.43800 (18)0.30247 (18)0.0520 (4)
C20.0232 (2)0.60329 (19)0.12899 (18)0.0517 (4)
H20.06290.65300.07090.062*
C30.12533 (18)0.62301 (16)0.12273 (15)0.0416 (4)
C40.18811 (18)0.54624 (15)0.20539 (15)0.0401 (3)
H40.28670.55770.20110.048*
C4A0.10195 (18)0.45140 (16)0.29532 (15)0.0419 (4)
C50.2583 (2)0.31688 (19)0.42779 (17)0.0543 (4)
H50.34870.35790.38650.065*
C5A0.13211 (19)0.35540 (17)0.39217 (15)0.0453 (4)
C60.2482 (3)0.2166 (2)0.52573 (19)0.0676 (6)
H60.33240.18990.55040.081*
C70.1124 (3)0.1549 (2)0.5879 (2)0.0734 (6)
H70.10750.08830.65420.088*
C80.0125 (3)0.1898 (2)0.5540 (2)0.0703 (6)
H80.10210.14760.59570.084*
C8A0.0034 (2)0.2901 (2)0.45538 (18)0.0561 (5)
C9A0.2762 (7)0.3251 (7)0.4616 (7)0.0659 (19)0.484 (8)
H9A0.33450.40830.44490.079*0.484 (8)
H9B0.30180.30840.55340.079*0.484 (8)
C10A0.3076 (6)0.2029 (6)0.4029 (5)0.0791 (19)0.484 (8)
H10A0.28530.22270.31270.119*0.484 (8)
H10B0.41230.18500.44160.119*0.484 (8)
H10C0.24530.12270.41680.119*0.484 (8)
C9B0.2572 (8)0.2771 (7)0.4206 (7)0.0691 (17)0.516 (8)
H9C0.28220.28500.34240.083*0.516 (8)
H9D0.25060.17960.44810.083*0.516 (8)
C10B0.3732 (7)0.3585 (7)0.5226 (7)0.103 (2)0.516 (8)
H10D0.35990.33310.60360.154*0.516 (8)
H10E0.47260.33860.52660.154*0.516 (8)
H10F0.36140.45610.50300.154*0.516 (8)
C110.20888 (18)0.73320 (16)0.02609 (15)0.0430 (4)
H110.20100.71570.05690.052*
C120.1339 (2)0.87624 (17)0.06181 (17)0.0494 (4)
H120.04320.90350.04740.059*
C130.1939 (2)0.96398 (16)0.11316 (16)0.0480 (4)
C140.3342 (2)0.93001 (16)0.13989 (15)0.0460 (4)
C150.3859 (2)1.0075 (2)0.21574 (18)0.0600 (5)
H150.32931.08760.25120.072*
C160.5189 (3)0.9670 (2)0.2385 (2)0.0706 (6)
H160.55241.02060.28780.085*
C170.6030 (3)0.8471 (2)0.1887 (2)0.0671 (5)
H170.69350.82090.20370.081*
C180.5531 (2)0.7658 (2)0.11633 (18)0.0539 (4)
H180.60770.68300.08600.065*
C190.42161 (19)0.80795 (17)0.08919 (15)0.0435 (4)
N200.37072 (15)0.73058 (13)0.00993 (12)0.0422 (3)
C210.4711 (2)0.65973 (18)0.08888 (17)0.0507 (4)
H210.57380.66700.10550.061*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl10.0821 (4)0.0428 (3)0.0766 (4)0.0104 (2)0.0184 (3)0.0106 (2)
O10.0611 (8)0.0675 (9)0.0684 (9)0.0077 (7)0.0100 (7)0.0277 (7)
N10.0474 (9)0.0711 (11)0.0782 (11)0.0233 (8)0.0099 (8)0.0174 (9)
C10.0393 (9)0.0595 (11)0.0771 (13)0.0107 (8)0.0183 (9)0.0010 (9)
C1A0.0447 (9)0.0476 (9)0.0584 (10)0.0107 (7)0.0086 (8)0.0005 (8)
C20.0457 (10)0.0513 (10)0.0606 (11)0.0019 (7)0.0213 (8)0.0024 (8)
C30.0426 (9)0.0368 (8)0.0432 (8)0.0038 (6)0.0102 (7)0.0059 (6)
C40.0386 (8)0.0377 (8)0.0427 (8)0.0055 (6)0.0104 (6)0.0061 (6)
C4A0.0425 (9)0.0367 (8)0.0432 (8)0.0070 (6)0.0078 (7)0.0069 (6)
C50.0615 (11)0.0567 (11)0.0442 (9)0.0127 (8)0.0156 (8)0.0014 (8)
C5A0.0519 (10)0.0408 (8)0.0388 (8)0.0105 (7)0.0069 (7)0.0048 (6)
C60.0797 (15)0.0723 (14)0.0509 (11)0.0089 (11)0.0237 (10)0.0090 (10)
C70.0952 (17)0.0652 (13)0.0514 (11)0.0148 (12)0.0151 (11)0.0147 (9)
C80.0750 (14)0.0645 (13)0.0594 (12)0.0230 (11)0.0052 (10)0.0111 (10)
C8A0.0576 (11)0.0510 (10)0.0519 (10)0.0127 (8)0.0062 (8)0.0004 (8)
C9A0.047 (4)0.056 (4)0.078 (5)0.012 (3)0.005 (4)0.007 (3)
C10A0.058 (3)0.078 (4)0.100 (4)0.024 (3)0.019 (3)0.010 (3)
C9B0.065 (4)0.066 (4)0.073 (4)0.032 (4)0.010 (3)0.005 (3)
C10B0.056 (4)0.123 (5)0.110 (4)0.025 (3)0.008 (3)0.024 (4)
C110.0460 (9)0.0399 (8)0.0421 (8)0.0033 (6)0.0136 (7)0.0013 (6)
C120.0507 (10)0.0419 (9)0.0521 (10)0.0002 (7)0.0151 (8)0.0042 (7)
C130.0571 (10)0.0351 (8)0.0439 (9)0.0011 (7)0.0076 (7)0.0008 (7)
C140.0551 (10)0.0392 (8)0.0388 (8)0.0101 (7)0.0085 (7)0.0023 (6)
C150.0774 (14)0.0483 (10)0.0530 (11)0.0133 (9)0.0169 (9)0.0063 (8)
C160.0865 (16)0.0694 (14)0.0677 (13)0.0213 (12)0.0356 (12)0.0097 (10)
C170.0667 (13)0.0736 (14)0.0700 (13)0.0153 (10)0.0326 (10)0.0003 (11)
C180.0531 (10)0.0510 (10)0.0558 (10)0.0075 (8)0.0155 (8)0.0007 (8)
C190.0461 (9)0.0414 (8)0.0397 (8)0.0122 (7)0.0088 (7)0.0028 (6)
N200.0441 (7)0.0374 (7)0.0411 (7)0.0066 (5)0.0084 (6)0.0010 (5)
C210.0474 (10)0.0461 (9)0.0527 (10)0.0069 (7)0.0070 (8)0.0069 (8)
Geometric parameters (Å, º) top
Cl1—C131.751 (2)C9A—H9B0.9700
O1—C211.212 (2)C10A—H10A0.9600
N1—C8A1.384 (3)C10A—H10B0.9600
N1—C1A1.390 (2)C10A—H10C0.9600
N1—C9A1.487 (7)C9B—C10B1.495 (8)
N1—C9B1.500 (7)C9B—H9C0.9700
C1—C21.378 (3)C9B—H9D0.9700
C1—C1A1.386 (3)C10B—H10D0.9601
C1—H10.9300C10B—H10E0.9601
C1A—C4A1.410 (2)C10B—H10F0.9601
C2—C31.408 (2)C11—N201.471 (2)
C2—H20.9300C11—C121.509 (2)
C3—C41.384 (2)C11—H110.9800
C3—C111.522 (2)C12—C131.326 (3)
C4—C4A1.396 (2)C12—H120.9300
C4—H40.9300C13—C141.450 (3)
C4A—C5A1.448 (2)C14—C151.401 (3)
C5—C5A1.384 (3)C14—C191.412 (2)
C5—C61.383 (3)C15—C161.374 (3)
C5—H50.9300C15—H150.9300
C5A—C8A1.414 (2)C16—C171.380 (3)
C6—C71.398 (3)C16—H160.9300
C6—H60.9300C17—C181.385 (3)
C7—C81.357 (3)C17—H170.9300
C7—H70.9300C18—C191.387 (3)
C8—C8A1.390 (3)C18—H180.9300
C8—H80.9300C19—N201.425 (2)
C9A—C10A1.494 (8)N20—C211.365 (2)
C9A—H9A0.9700C21—H210.9300
C8A—N1—C1A108.9 (2)C10B—C9B—H9C110.8
C8A—N1—C9A123.9 (3)N1—C9B—H9C110.8
C1A—N1—C9A124.8 (3)C10B—C9B—H9D110.8
C8A—N1—C9B125.4 (3)N1—C9B—H9D110.8
C2—C1—C1A117.8 (2)H9C—C9B—H9D108.8
C2—C1—H1121.1C9B—C10B—H10D109.5
C1A—C1—H1121.1C9B—C10B—H10E109.5
C1—C1A—N1129.7 (2)H10D—C10B—H10E109.5
C1—C1A—C4A121.6 (2)C9B—C10B—H10F109.5
N1—C1A—C4A108.7 (2)H10D—C10B—H10F109.5
C1—C2—C3121.9 (2)H10E—C10B—H10F109.5
C1—C2—H2119.0N20—C11—C12109.7 (1)
C3—C2—H2119.0N20—C11—C3113.9 (1)
C4—C3—C2119.8 (2)C12—C11—C3110.4 (1)
C4—C3—C11122.6 (2)N20—C11—H11107.5
C2—C3—C11117.5 (2)C12—C11—H11107.5
C3—C4—C4A119.3 (2)C3—C11—H11107.5
C3—C4—H4120.3C13—C12—C11121.7 (2)
C4A—C4—H4120.3C13—C12—H12119.2
C4—C4A—C1A119.5 (2)C11—C12—H12119.2
C4—C4A—C5A133.6 (2)C12—C13—C14123.0 (2)
C1A—C4A—C5A107.0 (1)C12—C13—Cl1119.6 (2)
C5A—C5—C6119.1 (2)C14—C13—Cl1117.4 (1)
C5A—C5—H5120.5C15—C14—C19118.0 (2)
C6—C5—H5120.5C15—C14—C13124.5 (2)
C5—C5A—C8A119.3 (2)C19—C14—C13117.5 (2)
C5—C5A—C4A134.3 (2)C16—C15—C14121.0 (2)
C8A—C5A—C4A106.3 (2)C16—C15—H15119.5
C5—C6—C7120.5 (2)C14—C15—H15119.5
C5—C6—H6119.7C15—C16—C17120.4 (2)
C7—C6—H6119.7C15—C16—H16119.8
C8—C7—C6121.6 (2)C17—C16—H16119.8
C8—C7—H7119.2C16—C17—C18120.2 (2)
C6—C7—H7119.2C16—C17—H17119.9
C7—C8—C8A118.4 (2)C18—C17—H17119.9
C7—C8—H8120.8C17—C18—C19119.9 (2)
C8A—C8—H8120.8C17—C18—H18120.0
N1—C8A—C8129.8 (2)C19—C18—H18120.0
N1—C8A—C5A109.1 (2)C18—C19—C14120.4 (2)
C8—C8A—C5A121.1 (2)C18—C19—N20121.5 (2)
N1—C9A—C10A105.6 (4)C14—C19—N20118.1 (2)
N1—C9A—H9A110.6C21—N20—C19121.1 (2)
C10A—C9A—H9A110.6C21—N20—C11117.9 (2)
N1—C9A—H9B110.6C19—N20—C11120.9 (2)
C10A—C9A—H9B110.6O1—C21—N20124.1 (2)
H9A—C9A—H9B108.8O1—C21—H21118.0
C10B—C9B—N1105.0 (5)N20—C21—H21118.0
C2—C1—C1A—N1179.7 (2)C8A—N1—C9A—C10A98.2 (6)
C2—C1—C1A—C4A1.4 (3)C1A—N1—C9A—C10A101.3 (5)
C8A—N1—C1A—C1177.9 (2)C9B—N1—C9A—C10A3.6 (9)
C9A—N1—C1A—C119.2 (5)C8A—N1—C9B—C10B97.1 (6)
C9B—N1—C1A—C111.2 (4)C1A—N1—C9B—C10B98.5 (5)
C8A—N1—C1A—C4A0.6 (2)C9A—N1—C9B—C10B1.3 (9)
C9A—N1—C1A—C4A162.3 (4)C4—C3—C11—N2012.0 (2)
C9B—N1—C1A—C4A167.2 (3)C2—C3—C11—N20169.9 (1)
C1A—C1—C2—C31.1 (3)C4—C3—C11—C12111.9 (2)
C1—C2—C3—C42.3 (3)C2—C3—C11—C1266.2 (2)
C1—C2—C3—C11175.8 (2)N20—C11—C12—C1321.5 (2)
C2—C3—C4—C4A0.9 (2)C3—C11—C12—C13104.8 (2)
C11—C3—C4—C4A177.1 (1)C11—C12—C13—C140.5 (3)
C3—C4—C4A—C1A1.6 (2)C11—C12—C13—Cl1178.1 (1)
C3—C4—C4A—C5A178.9 (2)C12—C13—C14—C15167.0 (1)
C1—C1A—C4A—C42.8 (3)Cl1—C13—C14—C1510.6 (2)
N1—C1A—C4A—C4178.6 (2)C12—C13—C14—C1910.9 (2)
C1—C1A—C4A—C5A177.5 (2)Cl1—C13—C14—C19171.5 (1)
N1—C1A—C4A—C5A1.1 (2)C19—C14—C15—C160.9 (3)
C6—C5—C5A—C8A0.9 (3)C13—C14—C15—C16178.8 (2)
C6—C5—C5A—C4A178.5 (2)C14—C15—C16—C171.2 (3)
C4—C4A—C5A—C53.7 (3)C15—C16—C17—C180.7 (3)
C1A—C4A—C5A—C5176.7 (2)C16—C17—C18—C192.8 (3)
C4—C4A—C5A—C8A178.5 (2)C17—C18—C19—C143.0 (3)
C1A—C4A—C5A—C8A1.1 (2)C17—C18—C19—N20176.9 (2)
C5A—C5—C6—C70.0 (3)C15—C14—C19—C181.2 (2)
C5—C6—C7—C80.7 (3)C13—C14—C19—C18176.8 (2)
C6—C7—C8—C8A0.4 (3)C15—C14—C19—N20178.8 (1)
C1A—N1—C8A—C8178.5 (2)C13—C14—C19—N203.2 (2)
C9A—N1—C8A—C818.4 (4)C18—C19—N20—C2132.7 (2)
C9B—N1—C8A—C812.1 (5)C14—C19—N20—C21147.2 (2)
C1A—N1—C8A—C5A0.1 (2)C18—C19—N20—C11151.9 (2)
C9A—N1—C8A—C5A163.2 (3)C14—C19—N20—C1128.2 (2)
C9B—N1—C8A—C5A166.3 (3)C12—C11—N20—C21139.7 (2)
C7—C8—C8A—N1177.8 (2)C3—C11—N20—C2196.0 (2)
C7—C8—C8A—C5A0.5 (3)C12—C11—N20—C1935.8 (2)
C5—C5A—C8A—N1177.4 (2)C3—C11—N20—C1988.5 (2)
C4A—C5A—C8A—N10.8 (2)C19—N20—C21—O1177.1 (2)
C5—C5A—C8A—C81.1 (3)C11—N20—C21—O17.4 (3)
C4A—C5A—C8A—C8179.4 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C4—H4···N200.932.552.882 (2)102
C11—H11···O10.982.372.751 (2)102
C15—H15···Cl10.932.693.085 (2)106
 

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