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In the title compound, C27H17ClO, the xanthene fused-ring system adopts a shallow butterfly conformation [dihedral angle between the two halves of the ring system = 22.9 (1)°. The dihedral angle between the central heteroyclic ring and the pendant chloro­phenyl group is 87.60 (8)°. In the crystal, mol­ecules are linked by weak C—H...π inter­actions.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S2414314618018461/hb4276sup1.cif
Contains datablocks global, New_Global_Publ_Block, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2414314618018461/hb4276Isup2.hkl
Contains datablock I

mol

MDL mol file https://doi.org/10.1107/S2414314618018461/hb4276Isup3.mol
Supplementary material

cml

Chemical Markup Language (CML) file https://doi.org/10.1107/S2414314618018461/hb4276Isup4.cml
Supplementary material

CCDC reference: 1887982

Key indicators

  • Single-crystal X-ray study
  • T = 296 K
  • Mean [sigma](C-C) = 0.003 Å
  • R factor = 0.046
  • wR factor = 0.053
  • Data-to-parameter ratio = 18.8

checkCIF/PLATON results

No syntax errors found



Datablock: I


Alert level B PLAT230_ALERT_2_B Hirshfeld Test Diff for Cl1 --C2 . 7.2 s.u.
Author Response: The Cl1 is closely associated with many H's around through C-H----Cl short distance contacts. Little variations in this association may invoke of site disorder and may involve complex coupled motions . The compound is synthetic and the structure was confirmed through NMR also. See _publ_section_exptl_prep and _publ_section_exptl_refinement
PLAT230_ALERT_2_B Hirshfeld Test Diff for    C13      --C14      .        8.5 s.u.
Author Response: The Cl1 is closely associated with many H's around through C-H----Cl short distance contacts. Little variations in this association may invoke of site disorder and may involve complex coupled motions . The compound is synthetic and the structure was confirmed through NMR also. See _publ_section_exptl_prep and _publ_section_exptl_refinement
PLAT230_ALERT_2_B Hirshfeld Test Diff for    C21      --C22      .        7.5 s.u.
Author Response: The Cl1 is closely associated with many H's around through C-H----Cl short distance contacts. Little variations in this association may invoke of site disorder and may involve complex coupled motions . The compound is synthetic and the structure was confirmed through NMR also. See _publ_section_exptl_prep and _publ_section_exptl_refinement
PLAT910_ALERT_3_B Missing # of FCF Reflection(s) Below Theta(Min).         12 Note

Alert level C GOODF01_ALERT_2_C The least squares goodness of fit parameter lies outside the range 0.80 <> 2.00 Goodness of fit given = 0.607
Author Response: This range of the goodness of fit is normal for good structures determined for a series of 14-(4-aryl)-14H-dibenzo[a,j]xanthene compounds as studied in our laboratory.
PLAT230_ALERT_2_C Hirshfeld Test Diff for    C2       --C3       .        5.4 s.u.
Author Response: The Cl1 is closely associated with many H's around through C-H----Cl short distance contacts. Little variations in this association may invoke of site disorder and may involve complex coupled motions . The compound is synthetic and the structure was confirmed through NMR also. See _publ_section_exptl_prep and _publ_section_exptl_refinement
PLAT242_ALERT_2_C Low    'MainMol' Ueq as Compared to Neighbors of         C2 Check
Author Response: Temperature modifies the diffraction intensities. False alarms may also be due to the group being in terminal.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H31      ..CL1      .       3.00 Ang.

Alert level G PLAT005_ALERT_5_G No Embedded Refinement Details Found in the CIF Please Do ! PLAT808_ALERT_5_G No Parseable SHELXL Style Weighting Scheme Found Please Check PLAT882_ALERT_1_G No Datum for _diffrn_reflns_av_unetI/netI ...... Please Do ! PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L= 0.600 8 Note PLAT929_ALERT_5_G No Weight Pars,Obs and Calc R1,wR2,S not Checked ! Info PLAT960_ALERT_3_G Number of Intensities with I < - 2*sig(I) ... 3 Check
0 ALERT level A = Most likely a serious problem - resolve or explain 4 ALERT level B = A potentially serious problem, consider carefully 4 ALERT level C = Check. Ensure it is not caused by an omission or oversight 6 ALERT level G = General information/check it is not something unexpected 1 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 2 ALERT type 3 Indicator that the structure quality may be low 2 ALERT type 4 Improvement, methodology, query or suggestion 3 ALERT type 5 Informative message, check

Computing details top

Data collection: APEX2 (Bruker, 2010); cell refinement: SAINT (Bruker, 2010); data reduction: SAINT (Bruker, 2010); program(s) used to solve structure: Superflip (Palatinus & Chapuis, 2007); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: Mercury (Macrae et al., 2008), CAMERON (Watkin et al., 2003) and ORTEP-3 for Windows (Farrugia, 2012); software used to prepare material for publication: CRYSTALS (Betteridge et al., 2003).

14-(4-Chlorophenyl)-14H-dibenzo[a,j]xanthene top
Crystal data top
C27H17ClOF(000) = 815.997
Mr = 392.88Dx = 1.354 Mg m3
Orthorhombic, Pna21Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2nCell parameters from 9942 reflections
a = 14.0201 (7) Åθ = 2.8–24.1°
b = 17.4488 (8) ŵ = 0.21 mm1
c = 7.8775 (3) ÅT = 296 K
V = 1927.10 (15) Å3Needle, colourless
Z = 40.40 × 0.21 × 0.10 mm
Data collection top
BRUKER SMART APEXII
diffractometer
4052 reflections with I > 2.0σ(I)
Graphite monochromatorRint = 0.034
ω/2θ scansθmax = 29.0°, θmin = 2.3°
Absorption correction: multi-scan
(SADABS; Bruker, 2010)
h = 1918
Tmin = 0.853, Tmax = 1k = 2323
34384 measured reflectionsl = 1010
4980 independent reflections
Refinement top
Refinement on F2H-atom parameters constrained
Least-squares matrix: full Method = Quasi-Unit weights W = 1.0 or 1./4Fsq
R[F2 > 2σ(F2)] = 0.046(Δ/σ)max = 0.0002
wR(F2) = 0.053Δρmax = 0.42 e Å3
S = 0.61Δρmin = 0.41 e Å3
4970 reflectionsExtinction correction: Larson (1970), Equation 22
264 parametersExtinction coefficient: 140 (3)
1 restraintAbsolute structure: Flack (1983), 2260 Friedel-pairs
Primary atom site location: structure-invariant direct methodsAbsolute structure parameter: 0.15 (5)
Hydrogen site location: difference Fourier map
Special details top

Experimental. The crystal was placed in the cold stream of an Oxford Cryosystems open-flow nitrogen cryostat (Cosier & Glazer, 1986) with a nominal stability of 0.1K.

Cosier, J. & Glazer, A.M., 1986. J. Appl. Cryst. 105-107.

Refinement. The H atoms attached to carbon atoms were located in difference maps and refined as riding atoms in their as-found relative locations.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Cl10.42137 (5)0.44109 (4)0.49033 (11)0.0905
C20.35101 (15)0.45059 (11)0.3081 (3)0.0525
C30.39356 (14)0.44159 (12)0.1537 (3)0.0574
C40.33832 (12)0.44586 (10)0.0064 (3)0.0498
C50.24104 (11)0.45958 (9)0.0168 (2)0.0386
C60.17853 (13)0.46716 (10)0.1418 (2)0.0421
C70.13553 (13)0.54701 (11)0.1471 (2)0.0450
C80.19136 (16)0.61195 (11)0.1980 (3)0.0500
C90.28621 (16)0.60620 (11)0.2561 (2)0.0560
C100.3369 (2)0.66973 (14)0.3063 (3)0.0747
C110.2959 (3)0.74292 (15)0.2984 (3)0.0821
C120.2059 (3)0.75021 (14)0.2438 (3)0.0776
C130.15026 (18)0.68635 (12)0.1914 (3)0.0626
C140.0552 (2)0.69352 (14)0.1342 (3)0.0734
C150.00195 (19)0.63196 (14)0.0875 (3)0.0676
C160.04440 (15)0.55834 (13)0.0970 (2)0.0531
O170.01588 (9)0.49912 (9)0.04831 (19)0.0608
C180.01068 (14)0.42485 (12)0.0923 (2)0.0512
C190.10051 (13)0.40635 (10)0.1441 (2)0.0415
C200.11915 (14)0.32913 (10)0.1936 (2)0.0446
C210.04471 (16)0.27372 (11)0.1814 (3)0.0533
C220.04492 (17)0.29705 (15)0.1219 (3)0.0675
C230.06320 (15)0.37023 (14)0.0807 (3)0.0640
H2310.12410.38560.03000.0765*
H2210.09360.25770.09940.0807*
C240.0624 (2)0.19770 (13)0.2329 (3)0.0734
C250.1482 (2)0.17598 (14)0.2956 (3)0.0773
C260.22213 (19)0.22971 (12)0.3076 (3)0.0651
C270.20808 (16)0.30473 (11)0.2575 (2)0.0520
H2710.25830.33930.26050.0622*
H2610.28490.21880.36690.0779*
H2510.15670.12110.33860.0907*
H2410.01280.16080.23090.0876*
H1510.06220.63730.04940.0807*
H1410.03010.74350.12360.0901*
H1210.17660.79740.22870.0959*
H1110.33190.78830.34720.0967*
H1010.40310.66290.35240.0904*
H910.31540.55760.25990.0665*
H610.21750.46240.24490.0468*
C280.20141 (14)0.46887 (11)0.1766 (2)0.0480
C290.25589 (15)0.46442 (12)0.3222 (3)0.0562
H2910.22940.47130.43030.0667*
H2810.13590.48060.18230.0578*
H410.36640.43800.09750.0603*
H310.46310.43390.15100.0692*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl10.0832 (4)0.0975 (5)0.0909 (4)0.0033 (4)0.0486 (4)0.0036 (4)
C20.0583 (14)0.0418 (11)0.0575 (12)0.0032 (10)0.0252 (11)0.0022 (11)
C30.0360 (11)0.0498 (13)0.0865 (17)0.0012 (10)0.0105 (11)0.0150 (12)
C40.0424 (11)0.0476 (11)0.0594 (12)0.0034 (9)0.0046 (10)0.0093 (11)
C50.0357 (10)0.0311 (9)0.0491 (11)0.0013 (8)0.0018 (8)0.0044 (9)
C60.0449 (11)0.0408 (10)0.0405 (11)0.0050 (9)0.0021 (8)0.0026 (9)
C70.0536 (12)0.0419 (12)0.0394 (11)0.0128 (9)0.0049 (9)0.0008 (9)
C80.0719 (14)0.0398 (11)0.0384 (10)0.0114 (11)0.0111 (10)0.0008 (9)
C90.0712 (15)0.0424 (12)0.0545 (12)0.0005 (11)0.0016 (11)0.0066 (10)
C100.095 (2)0.0604 (16)0.0690 (16)0.0117 (15)0.0041 (15)0.0122 (13)
C110.123 (3)0.0550 (16)0.0678 (17)0.0101 (17)0.0063 (17)0.0167 (14)
C120.128 (3)0.0348 (12)0.0703 (16)0.0099 (16)0.0237 (18)0.0007 (12)
C130.0924 (19)0.0497 (13)0.0456 (12)0.0178 (13)0.0176 (13)0.0033 (11)
C140.107 (2)0.0504 (14)0.0633 (16)0.0345 (15)0.0264 (15)0.0132 (12)
C150.0720 (16)0.0778 (17)0.0530 (13)0.0381 (14)0.0086 (11)0.0146 (12)
C160.0582 (13)0.0574 (13)0.0437 (11)0.0146 (12)0.0062 (9)0.0008 (11)
O170.0489 (8)0.0754 (9)0.0579 (9)0.0158 (8)0.0042 (8)0.0039 (8)
C180.0491 (12)0.0642 (15)0.0402 (11)0.0059 (11)0.0013 (9)0.0003 (10)
C190.0414 (10)0.0498 (11)0.0333 (10)0.0023 (9)0.0024 (8)0.0004 (9)
C200.0503 (12)0.0500 (11)0.0336 (10)0.0023 (10)0.0067 (9)0.0037 (9)
C210.0579 (14)0.0571 (13)0.0449 (12)0.0095 (11)0.0116 (11)0.0032 (11)
C220.0643 (16)0.0761 (17)0.0620 (16)0.0216 (14)0.0075 (12)0.0140 (13)
C230.0445 (12)0.0964 (19)0.0510 (13)0.0026 (13)0.0015 (10)0.0089 (13)
C240.090 (2)0.0611 (16)0.0694 (18)0.0232 (15)0.0155 (14)0.0003 (13)
C250.115 (2)0.0465 (14)0.0704 (17)0.0047 (16)0.0155 (16)0.0081 (13)
C260.0816 (18)0.0576 (15)0.0561 (14)0.0121 (13)0.0042 (13)0.0099 (12)
C270.0613 (14)0.0463 (12)0.0484 (12)0.0019 (11)0.0060 (11)0.0026 (10)
C280.0405 (10)0.0547 (12)0.0488 (11)0.0079 (10)0.0018 (10)0.0024 (10)
C290.0563 (13)0.0629 (13)0.0494 (12)0.0067 (11)0.0070 (10)0.0038 (12)
Geometric parameters (Å, º) top
Cl1—C21.7496 (19)C14—H1410.944
C2—C31.364 (3)C15—C161.418 (3)
C2—C291.360 (3)C15—H1510.953
C3—C41.397 (3)C16—O171.389 (2)
C3—H310.985O17—C181.392 (2)
C4—C51.387 (2)C18—C191.363 (2)
C4—H410.919C18—C231.411 (3)
C5—C61.532 (2)C19—C201.427 (2)
C5—C281.386 (3)C20—C211.426 (2)
C6—C71.519 (3)C20—C271.410 (3)
C6—C191.524 (3)C21—C221.402 (3)
C6—H610.983C21—C241.409 (3)
C7—C81.435 (3)C22—C231.342 (3)
C7—C161.352 (3)C22—H2210.985
C8—C91.410 (3)C23—H2310.981
C8—C131.421 (3)C24—C251.355 (3)
C9—C101.375 (3)C24—H2410.947
C9—H910.943C25—C261.401 (3)
C10—C111.401 (3)C25—H2511.022
C10—H1011.005C26—C271.381 (3)
C11—C121.339 (4)C26—H2611.014
C11—H1111.014C27—H2710.928
C12—C131.422 (3)C28—C291.380 (3)
C12—H1210.927C28—H2810.942
C13—C141.412 (3)C29—H2910.937
C14—C151.359 (3)
Cl1—C2—C3118.32 (16)C14—C15—H151121.8
Cl1—C2—C29120.18 (18)C16—C15—H151120.1
C3—C2—C29121.47 (19)C15—C16—C7123.0 (2)
C2—C3—C4119.48 (18)C15—C16—O17113.84 (19)
C2—C3—H31117.9C7—C16—O17123.15 (19)
C4—C3—H31122.6C16—O17—C18117.46 (14)
C3—C4—C5120.4 (2)O17—C18—C19122.84 (18)
C3—C4—H41119.7O17—C18—C23114.62 (18)
C5—C4—H41120.0C19—C18—C23122.54 (19)
C4—C5—C6121.96 (18)C6—C19—C18119.65 (17)
C4—C5—C28117.91 (19)C6—C19—C20121.97 (16)
C6—C5—C28120.10 (15)C18—C19—C20118.35 (17)
C5—C6—C7109.18 (15)C19—C20—C21119.20 (17)
C5—C6—C19111.12 (14)C19—C20—C27122.99 (17)
C7—C6—C19110.71 (15)C21—C20—C27117.80 (17)
C5—C6—H61110.4C20—C21—C22118.80 (19)
C7—C6—H61106.1C20—C21—C24119.4 (2)
C19—C6—H61109.3C22—C21—C24121.8 (2)
C6—C7—C8121.05 (16)C21—C22—C23121.9 (2)
C6—C7—C16120.09 (18)C21—C22—H221118.6
C8—C7—C16118.81 (19)C23—C22—H221119.2
C7—C8—C9123.31 (18)C18—C23—C22119.1 (2)
C7—C8—C13119.34 (19)C18—C23—H231118.8
C9—C8—C13117.3 (2)C22—C23—H231121.7
C8—C9—C10121.5 (2)C21—C24—C25121.6 (2)
C8—C9—H91119.0C21—C24—H241120.4
C10—C9—H91119.5C25—C24—H241117.9
C9—C10—C11120.7 (3)C24—C25—C26119.6 (2)
C9—C10—H101119.1C24—C25—H251119.1
C11—C10—H101120.1C26—C25—H251121.2
C10—C11—C12119.1 (3)C25—C26—C27120.6 (2)
C10—C11—H111119.4C25—C26—H261123.2
C12—C11—H111121.1C27—C26—H261115.6
C11—C12—C13122.4 (3)C20—C27—C26120.9 (2)
C11—C12—H121122.9C20—C27—H271119.0
C13—C12—H121114.5C26—C27—H271120.0
C12—C13—C8118.9 (2)C5—C28—C29121.77 (18)
C12—C13—C14122.8 (2)C5—C28—H281117.3
C8—C13—C14118.4 (2)C29—C28—H281120.8
C13—C14—C15122.3 (2)C28—C29—C2119.0 (2)
C13—C14—H141117.5C28—C29—H291121.9
C15—C14—H141120.1C2—C29—H291119.0
C14—C15—C16118.1 (2)
Hydrogen-bond geometry (Å, º) top
Cg2 and Cg4 are the centroids of the C2–C5/C28/C29 and C8–C13 rings, respectively.
D—H···AD—HH···AD···AD—H···A
C3—H31···Cl1i0.983.003.547 (2)116
C12—H121···Cg2ii0.932.903.649 (3)138
C23—H231···Cg4iii0.983.003.740 (3)134
C25—H251···Cg2iv1.022.973.942 (3)160
Symmetry codes: (i) x+1, y+1, z+1/2; (ii) x+1/2, y+1/2, z+1/2; (iii) x, y+1, z1/2; (iv) x+1/2, y1/2, z+1/2.
 

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