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The title compound, C14H13Cl, consists of two central non-planar six-membered carbon rings constituting a bicyclic system, having a benzene ring fused on one side and a >CHCH2Cl moiety, bridging the two C atoms of the bicyclic system, thereby forming a fused three-atom ring on the other side. The bicyclic system has approximate D3 symmetry and all three six-membered rings adopt boat conformations.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536804001904/na6290sup1.cif
Contains datablocks 2, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536804001904/na62902sup2.hkl
Contains datablock 2

CCDC reference: 236069

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.003 Å
  • R factor = 0.042
  • wR factor = 0.097
  • Data-to-parameter ratio = 15.1

checkCIF/PLATON results

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Alert level C REFLT03_ALERT_3_C Reflection count < 95% complete From the CIF: _diffrn_reflns_theta_max 28.02 From the CIF: _diffrn_reflns_theta_full 0.00 From the CIF: _reflns_number_total 2590 TEST2: Reflns within _diffrn_reflns_theta_max Count of symmetry unique reflns 2728 Completeness (_total/calc) 94.94% PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd. # 1 C14 H13 Cl
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 2 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 1 ALERT type 3 Indicator that the structure quality may be low 1 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: SMART (Bruker, 1999); cell refinement: SMART; data reduction: SAINT (Bruker, 1999) and SHELXTL (Bruker, 1999); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).

(2) top
Crystal data top
C14H13ClF(000) = 456
Mr = 216.69Dx = 1.278 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 2865 reflections
a = 8.0400 (8) Åθ = 2.3–28.0°
b = 7.8514 (7) ŵ = 0.30 mm1
c = 18.1877 (16) ÅT = 293 K
β = 101.133 (2)°Irregular, colourless
V = 1126.50 (18) Å30.30 × 0.25 × 0.10 mm
Z = 4
Data collection top
Nonius KappaCCD
diffractometer
1441 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.037
Graphite monochromatorθmax = 28.0°, θmin = 2.3°
Detector resolution: 6.67 pixels mm-1h = 810
φ and ω scansk = 1010
6442 measured reflectionsl = 2319
2590 independent reflections
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)] = 0.042Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.098H atoms treated by a mixture of independent and constrained refinement
S = 0.85 w = 1/[σ2(Fo2) + (0.047P)2]
where P = (Fo2 + 2Fc2)/3
2590 reflections(Δ/σ)max < 0.001
172 parametersΔρmax = 0.14 e Å3
0 restraintsΔρmin = 0.24 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*/Ueq
H510.001 (2)0.586 (2)0.3153 (9)0.045 (5)*
H1110.023 (2)0.270 (2)0.0706 (9)0.054 (5)*
H1310.384 (2)0.227 (2)0.0737 (8)0.046 (5)*
H210.122 (2)0.723 (3)0.0803 (11)0.073 (7)*
H710.248 (2)0.394 (2)0.2474 (10)0.046 (5)*
H1010.133 (2)0.538 (2)0.0223 (10)0.055 (5)*
H1210.088 (2)0.185 (2)0.1903 (9)0.051 (5)*
H910.417 (2)0.606 (2)0.0423 (10)0.061 (6)*
H810.474 (3)0.521 (2)0.1606 (10)0.063 (6)*
Cl10.26779 (8)0.04040 (7)0.02362 (3)0.0698 (2)
C120.1643 (2)0.2662 (2)0.15942 (9)0.0403 (4)
C60.0718 (2)0.5459 (2)0.20451 (9)0.0414 (4)
C110.1278 (3)0.3136 (2)0.08466 (9)0.0428 (4)
C10.0369 (2)0.5884 (2)0.13462 (10)0.0452 (5)
C130.2677 (3)0.1901 (2)0.08898 (10)0.0446 (5)
C70.2207 (2)0.4247 (2)0.19934 (11)0.0456 (5)
C50.0265 (3)0.6126 (3)0.26861 (12)0.0528 (5)
C100.1601 (3)0.5063 (2)0.07054 (11)0.0507 (5)
C140.2381 (3)0.0061 (2)0.07460 (10)0.0572 (6)
H14A0.12340.02430.09850.069*
H14B0.31560.06280.09680.069*
C90.3356 (3)0.5492 (2)0.08176 (13)0.0575 (6)
C80.3674 (3)0.5065 (2)0.14771 (14)0.0573 (6)
C20.0986 (3)0.6909 (2)0.12910 (13)0.0616 (6)
C30.1979 (3)0.7558 (3)0.19426 (14)0.0723 (7)
H30.28990.82530.19120.087*
C40.1612 (3)0.7184 (3)0.26259 (14)0.0669 (6)
H40.22740.76440.30560.080*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl10.0940 (5)0.0564 (3)0.0608 (3)0.0179 (3)0.0196 (3)0.0155 (3)
C120.0472 (12)0.0327 (10)0.0400 (10)0.0008 (8)0.0060 (9)0.0031 (8)
C60.0421 (11)0.0314 (9)0.0482 (11)0.0028 (8)0.0021 (8)0.0057 (8)
C110.0525 (12)0.0362 (10)0.0395 (10)0.0054 (9)0.0084 (9)0.0013 (8)
C10.0522 (12)0.0297 (9)0.0517 (11)0.0044 (8)0.0046 (9)0.0011 (8)
C130.0526 (13)0.0322 (10)0.0467 (11)0.0055 (9)0.0041 (9)0.0018 (8)
C70.0513 (13)0.0419 (11)0.0448 (11)0.0015 (9)0.0125 (9)0.0030 (9)
C50.0546 (14)0.0486 (12)0.0517 (13)0.0096 (10)0.0012 (10)0.0114 (10)
C100.0731 (16)0.0361 (11)0.0395 (11)0.0128 (10)0.0021 (10)0.0055 (8)
C140.0823 (16)0.0385 (12)0.0502 (11)0.0055 (10)0.0109 (11)0.0027 (8)
C90.0583 (15)0.0327 (10)0.0686 (14)0.0004 (10)0.0197 (12)0.0016 (10)
C80.0412 (13)0.0427 (12)0.0833 (17)0.0011 (10)0.0007 (12)0.0144 (11)
C20.0723 (16)0.0419 (12)0.0706 (15)0.0184 (11)0.0143 (12)0.0002 (11)
C30.0575 (15)0.0523 (13)0.104 (2)0.0178 (11)0.0072 (14)0.0118 (13)
C40.0544 (15)0.0549 (14)0.0807 (16)0.0005 (11)0.0134 (12)0.0243 (12)
Geometric parameters (Å, º) top
Cl1—C141.7935 (19)C7—H710.973 (17)
C12—C111.493 (2)C5—C41.386 (3)
C12—C131.509 (2)C5—H510.937 (16)
C12—C71.552 (2)C10—C91.503 (3)
C12—H1210.980 (17)C10—H1010.976 (18)
C6—C51.379 (2)C14—H14A0.9700
C6—C11.394 (2)C14—H14B0.9700
C6—C71.518 (2)C9—C81.317 (3)
C11—C131.499 (2)C9—H910.983 (19)
C11—C101.549 (2)C8—H810.94 (2)
C11—H1110.986 (17)C2—C31.391 (3)
C1—C21.373 (3)C2—H210.974 (19)
C1—C101.519 (3)C3—C41.363 (3)
C13—C141.495 (2)C3—H30.9300
C13—H1310.964 (16)C4—H40.9300
C7—C81.503 (3)
C11—C12—C1359.91 (11)C6—C5—C4119.3 (2)
C11—C12—C7110.67 (15)C6—C5—H51119.4 (11)
C13—C12—C7123.51 (16)C4—C5—H51121.3 (11)
C11—C12—H121118.2 (10)C9—C10—C1106.91 (16)
C13—C12—H121114.2 (10)C9—C10—C11109.16 (17)
C7—C12—H121117.3 (10)C1—C10—C11102.92 (15)
C5—C6—C1119.80 (18)C9—C10—H101116.2 (11)
C5—C6—C7127.33 (18)C1—C10—H101110.9 (11)
C1—C6—C7112.87 (15)C11—C10—H101109.9 (11)
C12—C11—C1360.60 (11)C13—C14—Cl1112.06 (13)
C12—C11—C10109.79 (16)C13—C14—H14A109.2
C13—C11—C10122.51 (18)Cl1—C14—H14A109.2
C12—C11—H111118.6 (10)C13—C14—H14B109.2
C13—C11—H111118.5 (10)Cl1—C14—H14B109.2
C10—C11—H111114.7 (10)H14A—C14—H14B107.9
C2—C1—C6120.58 (18)C8—C9—C10114.79 (19)
C2—C1—C10126.94 (19)C8—C9—H91124.1 (11)
C6—C1—C10112.46 (16)C10—C9—H91121.1 (11)
C14—C13—C11117.98 (18)C9—C8—C7114.3 (2)
C14—C13—C12116.79 (17)C9—C8—H81123.0 (12)
C11—C13—C1259.49 (11)C7—C8—H81122.6 (12)
C14—C13—H131114.7 (10)C1—C2—C3119.0 (2)
C11—C13—H131118.9 (10)C1—C2—H21120.8 (12)
C12—C13—H131118.0 (10)C3—C2—H21120.1 (12)
C8—C7—C6106.56 (16)C4—C3—C2120.5 (2)
C8—C7—C12108.37 (15)C4—C3—H3119.7
C6—C7—C12103.53 (15)C2—C3—H3119.7
C8—C7—H71112.4 (10)C3—C4—C5120.71 (19)
C6—C7—H71114.4 (10)C3—C4—H4119.6
C12—C7—H71111.0 (10)C5—C4—H4119.6
C7—C12—C11—C13117.60 (17)C7—C6—C5—C4178.16 (17)
C13—C12—C11—C10116.93 (18)C2—C1—C10—C9129.1 (2)
C7—C12—C11—C100.7 (2)C6—C1—C10—C952.3 (2)
C5—C6—C1—C22.5 (3)C2—C1—C10—C11115.9 (2)
C7—C6—C1—C2177.07 (17)C6—C1—C10—C1162.7 (2)
C5—C6—C1—C10178.79 (17)C12—C11—C10—C953.0 (2)
C7—C6—C1—C101.6 (2)C13—C11—C10—C914.0 (2)
C12—C11—C13—C14106.22 (19)C12—C11—C10—C160.3 (2)
C10—C11—C13—C14157.95 (16)C13—C11—C10—C1127.35 (18)
C10—C11—C13—C1295.83 (19)C11—C13—C14—Cl180.2 (2)
C11—C12—C13—C14108.2 (2)C12—C13—C14—Cl1148.09 (15)
C7—C12—C13—C14155.72 (18)C1—C10—C9—C854.8 (2)
C7—C12—C13—C1196.06 (19)C11—C10—C9—C855.8 (2)
C5—C6—C7—C8125.8 (2)C10—C9—C8—C70.7 (2)
C1—C6—C7—C854.7 (2)C6—C7—C8—C954.3 (2)
C5—C6—C7—C12120.03 (19)C12—C7—C8—C956.6 (2)
C1—C6—C7—C1259.52 (18)C6—C1—C2—C31.8 (3)
C11—C12—C7—C854.3 (2)C10—C1—C2—C3179.71 (19)
C13—C12—C7—C812.6 (2)C1—C2—C3—C40.0 (3)
C11—C12—C7—C658.57 (18)C2—C3—C4—C51.2 (3)
C13—C12—C7—C6125.44 (17)C6—C5—C4—C30.5 (3)
C1—C6—C5—C41.4 (3)
 

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