organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

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ISSN: 2056-9890

(Z)-9-(1,2-Di­chloro­vin­yl)-9H-carbazole

aDepartment of Material Science and Chemistry, Wakayama University, Sakaedani, Wakayama, 640-8510, Japan
*Correspondence e-mail: okuno@center.wakayama-u.ac.jp

(Received 8 March 2013; accepted 14 March 2013; online 20 March 2013)

There are two independent mol­ecules in the asymmetric unit of the title compound, C14H9Cl2N, in which the dihedral angles between the dichloro­vinyl unit (r.m.s. deviations = 0.0003 and 0.0009 Å), and the carbazole ring are 87.77 (3) and 72.90 (3)°.

Related literature

For the preparation of the title compound, see: Okamoto & Kundu (1970[Okamoto, Y. & Kundu, S. K. (1970). J. Org. Chem. 35, 4250-4252.]); Cuniberti et al. (1996[Cuniberti, C., Dellepiane, G., Piaggio, P., Franco, R., Musso, G. F. C., Dell'Erba, C. & Garbarino, G. (1996). Chem. Mater. 8, 708-713.]). For the structure of 9-vinyl­carbazole, see: Tsutsui et al. (1976[Tsutsui, K., Hirotsu, K., Umesaki, M., Kurahashi, M., Shimada, A. & Higuchi, T. (1976). Acta Cryst. B32, 3049-3053.]); Tian et al. (2006[Tian, X., Shi, W., Shen, K., Li, C., Lin, J., Che, Y. & Zhang, P. (2006). J. Organomet. Chem. 691, 994-1006.]). For the optoelectric properties of vinyl­carbazoles, see: Ye et al. (2010[Ye, T., Chen, J. & Ma, D. (2010). Phys. Chem. Chem. Phys. 12, 15410-15413.]).

[Scheme 1]

Experimental

Crystal data
  • C14H9Cl2N

  • Mr = 262.14

  • Monoclinic, P 21 /c

  • a = 6.6552 (7) Å

  • b = 24.872 (3) Å

  • c = 14.8636 (15) Å

  • β = 93.7529 (16)°

  • V = 2455.1 (5) Å3

  • Z = 8

  • Mo Kα radiation

  • μ = 0.50 mm−1

  • T = 93 K

  • 0.14 × 0.11 × 0.07 mm

Data collection
  • Rigaku Saturn724+ diffractometer

  • Absorption correction: numerical (NUMABS; Rigaku, 1999[Rigaku (1999). NUMABS. Rigaku Corporation, Tokyo, Japan.]) Tmin = 0.939, Tmax = 0.965

  • 19841 measured reflections

  • 5595 independent reflections

  • 5154 reflections with F2 > 2σ(F2)

  • Rint = 0.024

Refinement
  • R[F2 > 2σ(F2)] = 0.035

  • wR(F2) = 0.092

  • S = 1.04

  • 5594 reflections

  • 323 parameters

  • H-atom parameters constrained

  • Δρmax = 0.60 e Å−3

  • Δρmin = −0.43 e Å−3

Data collection: CrystalClear (Rigaku, 2008[Rigaku (2008). CrystalClear. Rigaku Corporation, Tokyo, Japan.]); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SIR92 (Altomare et al., 1994[Altomare, A., Cascarano, G., Giacovazzo, C., Guagliardi, A., Burla, M. C., Polidori, G. & Camalli, M. (1994). J. Appl. Cryst. 27, 435.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: ORTEP-3 forWindows (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]); software used to prepare material for publication: CrystalStructure (Rigaku, 2010[Rigaku (2010). CrystalStructure. Rigaku Corporation, Tokyo, Japan.]).

Supporting information


Comment top

Vinylcarbazoles are interesting as monomers of poly(N-vinylcarbazoles) which have been attracted interest from the viewpoint of their optoelectric properties (Ye et al., 2010). The title compound, C14H9N1Cl2, is a halogen analogue of vinylcarbazole. In the literature (Okamoto & Kundu, 1970), the compoud is a mixture of E and Z forms. The crystals, however, were found to have only a Z form.

There are two independent molecules (A and B) in the asymmetric unit (Fig. 1). The carbazole rings are planar (N1/C1—C12 plane: r.m.s. deviation = 0.0194 Å, N2/C15—C26 plane: r.m.s. deviation = 0.0377 Å). The dichlorovinyl parts are also planar (Cl1/Cl2/C13/C14 plane: r.m.s. deviation = 0.0009 Å, Cl3/Cl4/C27/C28 plane: r.m.s. deviation = 0.0003 Å). The dihedral angles between the dichlorovinyl part and the carbazole ring are 87.77 (3)° for A and 72.90 (3)° for B, which are larger than those in vinylcarbazole (Tsutsui et al., 1976 and Tian et al., 2006), suggesting steric repulsion of the Cl1 or Cl3 with the hydrogen atoms of the carbazole rings. The inter-molecular contacts are dominated by C-H···π interactions which involve both six-membered rings of both molecules A and B (Fig. 2).

Related literature top

For the preparation of the title compound, see: Okamoto & Kundu (1970); Cuniberti et al. (1996). For the structure of 9-vinylcarbazole, see: Tsutsui et al. (1976); Tian et al. (2006). For the optoelectric properties of vinylcarbazoles, see: Ye et al. (2010).

Experimental top

The title compound was prepared according to a published procedure (Cuniberti et al., 1996). The single crystals with sufficient quality for X-ray analysis were grown slowly from the oilish mixture.

Refinement top

The C-bound H atoms were placed at ideal positions and were refined as riding on their parent C atoms. Uiso(H) values of the H atoms were set at 1.2Ueq(parent atom).

Computing details top

Data collection: CrystalClear (Rigaku, 2008); cell refinement: CrystalClear (Rigaku, 2008); data reduction: CrystalClear (Rigaku, 2008); program(s) used to solve structure: SIR92 (Altomare et al., 1994); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 forWindows (Farrugia, 2012); software used to prepare material for publication: CrystalStructure (Rigaku, 2010).

Figures top
[Figure 1] Fig. 1. The asymmetric unit of the title compound with atom-numbering scheme. Displacement ellipsoids are drawn at the 50% probability level and H atoms are shown as small spheres.
[Figure 2] Fig. 2. A portion of the lattice showing the C-H···π contacts with H atoms not involved in the C-H···π contacts omitted for clarity.
(Z)-9-(1,2-Dichlorovinyl)-9H-carbazole top
Crystal data top
C14H9Cl2NF(000) = 1072.00
Mr = 262.14Dx = 1.418 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71075 Å
Hall symbol: -P 2ybcCell parameters from 9066 reflections
a = 6.6552 (7) Åθ = 1.6–31.3°
b = 24.872 (3) ŵ = 0.50 mm1
c = 14.8636 (15) ÅT = 93 K
β = 93.7529 (16)°Block, colorless
V = 2455.1 (5) Å30.14 × 0.11 × 0.07 mm
Z = 8
Data collection top
Rigaku Saturn724+
diffractometer
5154 reflections with F2 > 2σ(F2)
Detector resolution: 28.445 pixels mm-1Rint = 0.024
ω scansθmax = 27.5°
Absorption correction: numerical
(NUMABS; Rigaku, 1999)
h = 88
Tmin = 0.939, Tmax = 0.965k = 3232
19841 measured reflectionsl = 1919
5595 independent reflections
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.035Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.092H-atom parameters constrained
S = 1.04 w = 1/[σ2(Fo2) + (0.0454P)2 + 1.5809P]
where P = (Fo2 + 2Fc2)/3
5594 reflections(Δ/σ)max < 0.001
323 parametersΔρmax = 0.60 e Å3
0 restraintsΔρmin = 0.43 e Å3
Primary atom site location: structure-invariant direct methods
Crystal data top
C14H9Cl2NV = 2455.1 (5) Å3
Mr = 262.14Z = 8
Monoclinic, P21/cMo Kα radiation
a = 6.6552 (7) ŵ = 0.50 mm1
b = 24.872 (3) ÅT = 93 K
c = 14.8636 (15) Å0.14 × 0.11 × 0.07 mm
β = 93.7529 (16)°
Data collection top
Rigaku Saturn724+
diffractometer
5595 independent reflections
Absorption correction: numerical
(NUMABS; Rigaku, 1999)
5154 reflections with F2 > 2σ(F2)
Tmin = 0.939, Tmax = 0.965Rint = 0.024
19841 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0350 restraints
wR(F2) = 0.092H-atom parameters constrained
S = 1.04Δρmax = 0.60 e Å3
5594 reflectionsΔρmin = 0.43 e Å3
323 parameters
Special details top

Refinement. Refinement was performed using all reflections except for one with very negative F2. The weighted R-factor (wR) and goodness of fit (S) are based on F2. R-factor (gt) are based on F. The threshold expression of F2 > 2.0 σ(F2) is used only for calculating R-factor (gt).

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Cl10.36938 (6)0.115051 (16)0.06836 (2)0.02685 (10)
Cl20.07609 (5)0.067708 (15)0.04789 (3)0.02598 (10)
Cl30.48776 (6)0.417277 (18)0.20176 (3)0.03522 (11)
Cl40.02371 (6)0.385892 (18)0.22034 (3)0.03179 (11)
N10.38706 (19)0.12141 (5)0.11169 (8)0.0220 (3)
N20.07119 (18)0.36020 (5)0.04603 (8)0.0187 (3)
C10.4098 (3)0.17400 (6)0.14528 (9)0.0208 (3)
C20.2888 (3)0.21869 (6)0.12645 (10)0.0237 (3)
C30.3395 (3)0.26575 (6)0.17308 (10)0.0255 (3)
C40.5047 (3)0.26787 (6)0.23673 (10)0.0263 (3)
C50.6246 (3)0.22303 (6)0.25421 (10)0.0240 (3)
C60.5777 (3)0.17551 (6)0.20749 (9)0.0209 (3)
C70.6640 (3)0.12206 (6)0.21095 (10)0.0216 (3)
C80.8266 (3)0.09901 (7)0.26128 (10)0.0264 (3)
C90.8666 (3)0.04476 (7)0.24977 (11)0.0284 (4)
C100.7481 (3)0.01371 (6)0.18843 (11)0.0267 (4)
C110.5848 (3)0.03562 (6)0.13764 (10)0.0246 (3)
C120.5451 (3)0.08984 (6)0.15036 (10)0.0213 (3)
C130.2646 (3)0.10640 (6)0.03541 (10)0.0205 (3)
C140.0817 (3)0.08677 (6)0.04245 (10)0.0231 (3)
C150.0809 (2)0.30780 (6)0.01076 (9)0.0184 (3)
C160.2113 (3)0.26628 (6)0.02964 (10)0.0220 (3)
C170.1905 (3)0.21842 (6)0.01740 (10)0.0243 (3)
C180.0458 (3)0.21255 (6)0.08086 (10)0.0260 (3)
C190.0838 (3)0.25415 (6)0.09896 (10)0.0246 (3)
C200.0660 (3)0.30276 (6)0.05279 (9)0.0202 (3)
C210.1688 (2)0.35412 (6)0.05645 (10)0.0210 (3)
C220.3168 (3)0.37452 (7)0.10978 (11)0.0271 (4)
C230.3715 (3)0.42804 (7)0.10051 (12)0.0305 (4)
C240.2833 (3)0.46122 (6)0.03795 (12)0.0282 (4)
C250.1378 (3)0.44174 (6)0.01656 (10)0.0230 (3)
C260.0810 (2)0.38833 (6)0.00524 (10)0.0192 (3)
C270.1707 (3)0.37955 (5)0.11931 (9)0.0188 (3)
C280.3629 (3)0.39276 (6)0.11315 (11)0.0246 (3)
H20.17930.21750.08770.0283*
H30.25360.29730.16120.0286*
H40.53260.30080.26960.0249*
H50.73540.22430.29850.0314*
H80.90820.12010.30260.0317*
H90.97580.02850.28400.0341*
H100.77970.02320.18120.0320*
H110.50420.01440.09610.0295*
H140.03470.08300.10110.0277*
H160.30980.27040.07260.0264*
H170.27660.18910.00620.0291*
H180.03630.17940.11210.0312*
H190.18250.24980.14170.0295*
H220.37870.35200.15160.0325*
H230.47020.44250.13710.0365*
H240.32380.49780.03270.0338*
H250.07950.46400.05970.0276*
H280.43620.38850.05660.0295*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl10.02329 (18)0.0368 (2)0.02081 (18)0.00867 (14)0.00395 (14)0.00355 (14)
Cl20.02099 (17)0.02764 (19)0.0290 (2)0.00531 (13)0.00099 (14)0.00015 (14)
Cl30.0287 (2)0.0402 (3)0.0383 (3)0.00770 (16)0.01367 (17)0.00693 (17)
Cl40.0270 (2)0.0474 (3)0.02074 (19)0.00283 (16)0.00039 (14)0.00556 (15)
N10.0252 (7)0.0203 (6)0.0198 (6)0.0011 (5)0.0025 (5)0.0015 (5)
N20.0192 (6)0.0178 (6)0.0196 (6)0.0010 (5)0.0057 (5)0.0012 (5)
C10.0248 (7)0.0215 (7)0.0160 (7)0.0014 (6)0.0019 (6)0.0020 (5)
C20.0239 (7)0.0259 (8)0.0211 (7)0.0025 (6)0.0001 (6)0.0015 (6)
C30.0283 (8)0.0239 (8)0.0249 (8)0.0028 (6)0.0056 (6)0.0018 (6)
C40.0326 (8)0.0246 (8)0.0222 (8)0.0035 (6)0.0052 (6)0.0055 (6)
C50.0270 (8)0.0271 (8)0.0178 (7)0.0031 (6)0.0009 (6)0.0026 (6)
C60.0232 (7)0.0242 (7)0.0155 (7)0.0007 (6)0.0019 (6)0.0006 (5)
C70.0244 (7)0.0240 (7)0.0166 (7)0.0003 (6)0.0027 (6)0.0008 (6)
C80.0268 (8)0.0333 (8)0.0189 (7)0.0004 (7)0.0010 (6)0.0018 (6)
C90.0275 (8)0.0336 (9)0.0241 (8)0.0049 (7)0.0015 (6)0.0083 (7)
C100.0311 (8)0.0233 (7)0.0264 (8)0.0039 (6)0.0065 (7)0.0061 (6)
C110.0291 (8)0.0226 (7)0.0221 (8)0.0001 (6)0.0025 (6)0.0017 (6)
C120.0238 (7)0.0229 (7)0.0173 (7)0.0002 (6)0.0016 (6)0.0033 (6)
C130.0236 (7)0.0190 (7)0.0189 (7)0.0001 (6)0.0016 (6)0.0015 (5)
C140.0246 (8)0.0236 (7)0.0212 (7)0.0016 (6)0.0020 (6)0.0012 (6)
C150.0200 (7)0.0191 (7)0.0161 (7)0.0023 (5)0.0003 (5)0.0013 (5)
C160.0222 (7)0.0223 (7)0.0216 (7)0.0014 (6)0.0024 (6)0.0006 (6)
C170.0285 (8)0.0191 (7)0.0246 (8)0.0019 (6)0.0033 (6)0.0005 (6)
C180.0347 (9)0.0215 (7)0.0210 (8)0.0050 (6)0.0039 (6)0.0043 (6)
C190.0290 (8)0.0271 (8)0.0179 (7)0.0058 (6)0.0028 (6)0.0028 (6)
C200.0217 (7)0.0228 (7)0.0162 (7)0.0027 (6)0.0016 (6)0.0010 (5)
C210.0202 (7)0.0243 (7)0.0187 (7)0.0021 (6)0.0027 (6)0.0014 (6)
C220.0236 (8)0.0345 (9)0.0238 (8)0.0008 (6)0.0073 (6)0.0024 (6)
C230.0232 (8)0.0380 (9)0.0310 (9)0.0032 (7)0.0078 (7)0.0097 (7)
C240.0233 (8)0.0254 (8)0.0359 (9)0.0034 (6)0.0017 (7)0.0067 (7)
C250.0216 (7)0.0210 (7)0.0265 (8)0.0014 (6)0.0025 (6)0.0016 (6)
C260.0174 (7)0.0217 (7)0.0189 (7)0.0008 (5)0.0031 (6)0.0031 (5)
C270.0215 (7)0.0173 (6)0.0178 (7)0.0000 (5)0.0037 (6)0.0006 (5)
C280.0229 (7)0.0264 (8)0.0249 (8)0.0025 (6)0.0047 (6)0.0028 (6)
Geometric parameters (Å, º) top
Cl1—C131.7470 (16)C18—C191.385 (3)
Cl2—C141.7162 (16)C19—C201.399 (2)
Cl3—C281.7146 (17)C20—C211.452 (2)
Cl4—C271.7448 (14)C21—C221.400 (3)
N1—C11.405 (2)C21—C261.406 (3)
N1—C121.4051 (19)C22—C231.384 (3)
N1—C131.4028 (19)C23—C241.401 (3)
N2—C151.405 (2)C24—C251.390 (3)
N2—C261.401 (2)C25—C261.388 (2)
N2—C271.3967 (19)C27—C281.318 (2)
C1—C21.390 (3)C2—H20.899
C1—C61.404 (2)C3—H30.979
C2—C31.391 (2)C4—H40.965
C3—C41.404 (3)C5—H50.956
C4—C51.386 (3)C8—H80.950
C5—C61.396 (2)C9—H90.950
C6—C71.448 (3)C10—H100.950
C7—C81.397 (3)C11—H110.950
C7—C121.409 (2)C14—H140.950
C8—C91.388 (3)C16—H160.950
C9—C101.398 (3)C17—H170.950
C10—C111.393 (3)C18—H180.950
C11—C121.390 (3)C19—H190.950
C13—C141.322 (3)C22—H220.950
C15—C161.389 (2)C23—H230.950
C15—C201.409 (2)C24—H240.950
C16—C171.392 (3)C25—H250.950
C17—C181.399 (3)C28—H280.950
Cl1···Cl23.2228 (6)C18···H5v2.7316
Cl1···C13.4920 (15)C19···H22.9494
Cl1···C123.4398 (16)C19···H5v2.7428
Cl3···Cl43.1799 (7)C20···H23.0357
Cl4···C253.5615 (16)C20···H33.3426
Cl4···C263.3171 (16)C20···H5v3.0889
N1···C53.597 (2)C20···H8v3.0187
N1···C83.600 (2)C21···H33.5416
N2···C193.599 (2)C21···H8v2.7081
N2···C223.597 (2)C21···H28viii3.1440
C1···C42.754 (2)C22···H8v2.9408
C1···C143.373 (2)C22···H28viii2.8988
C2···C52.838 (3)C23···H8v3.5261
C2···C133.103 (3)C23···H9v3.2336
C3···C62.776 (3)C23···H24vii3.3031
C5···C83.364 (3)C23···H28viii2.7690
C7···C102.777 (3)C24···H9v3.2476
C8···C112.840 (3)C24···H24vii2.9362
C9···C122.757 (3)C24···H25ix3.0478
C11···C133.086 (2)C24···H28viii2.8965
C12···C143.383 (2)C25···H24ix3.4426
C15···C182.750 (2)C25···H25ix2.9418
C15···C283.268 (3)C25···H28viii3.1508
C16···C192.845 (3)C26···H33.3872
C16···C273.121 (2)C26···H8v3.1601
C16···C283.552 (3)C26···H28viii3.2532
C17···C202.777 (3)C27···H33.5100
C19···C223.380 (3)C27···H24ix3.4402
C21···C242.779 (3)C28···H3x3.5917
C22···C252.835 (3)C28···H4x3.3679
C23···C262.753 (3)C28···H24ix2.9922
C25···C273.058 (2)H2···C153.0145
C26···C283.455 (3)H2···C162.9458
Cl3···C10i3.4335 (17)H2···C172.8276
C5···C18ii3.561 (3)H2···C182.8363
C6···C22iii3.544 (3)H2···C192.9494
C10···Cl3iv3.4335 (17)H2···C203.0357
C18···C5v3.561 (3)H2···H163.5041
C22···C6vi3.544 (3)H2···H173.3319
C24···C24vii3.590 (3)H2···H183.3495
C24···C28viii3.577 (3)H2···H193.5045
C25···C25ix3.447 (3)H3···Cl3viii3.4784
C28···C24x3.577 (3)H3···Cl43.0416
Cl1···H113.5722H3···N23.0933
Cl1···H143.5605H3···C153.0613
Cl4···H253.1879H3···C203.3426
Cl4···H283.5485H3···C213.5416
N1···H22.7730H3···C263.3872
N1···H112.7865H3···C273.5100
N1···H142.5278H3···C28viii3.5917
N2···H162.7844H3···H16viii3.3353
N2···H252.7733H3···H19iii3.2182
N2···H282.5438H3···H28viii3.4987
C1···H33.2509H4···Cl1iii3.4214
C1···H53.2864H4···Cl3viii3.0689
C1···H143.4021H4···C17ii3.5888
C2···H43.2978H4···C18ii3.4790
C3···H53.2923H4···C28viii3.3679
C4···H23.2460H4···H16viii3.2639
C5···H33.3121H4···H17ii3.4969
C5···H83.2340H4···H18ii3.3021
C6···H23.2674H4···H19iii3.0240
C6···H43.2685H5···C15ii3.4029
C6···H82.8858H5···C16ii3.4385
C7···H52.8814H5···C17ii3.0959
C7···H93.2564H5···C18ii2.7316
C7···H113.3123H5···C19ii2.7428
C8···H53.2289H5···C20ii3.0889
C8···H103.2721H5···H16viii3.5424
C9···H113.2980H5···H18ii3.0896
C10···H83.2826H5···H19ii3.1165
C11···H93.2855H5···H22iii3.1651
C12···H83.2874H8···C15ii3.5732
C12···H103.2344H8···C20ii3.0187
C12···H143.4323H8···C21ii2.7081
C13···H22.9366H8···C22ii2.9408
C13···H112.8985H8···C23ii3.5261
C14···H23.3756H8···C26ii3.1601
C14···H113.3896H8···H14viii3.2952
C15···H173.2313H8···H22ii3.2363
C15···H193.2881H8···H23iii3.4728
C15···H283.2084H9···Cl4xiv3.5625
C16···H183.2837H9···C23ii3.2336
C16···H283.4228H9···C24ii3.2476
C17···H193.2845H9···H14viii3.0855
C18···H163.2985H9···H23ii3.4952
C19···H173.2728H9···H24ii3.5198
C19···H223.2549H9···H25xiv2.8658
C20···H163.3147H10···Cl1xi2.9660
C20···H183.2517H10···Cl2xi3.0910
C20···H222.8968H10···Cl3iv3.0713
C21···H192.8921H10···Cl4xiv3.0947
C21···H233.2563H10···H14viii3.3971
C21···H253.3081H11···Cl1xi3.3608
C22···H193.2547H11···Cl2xii3.5410
C22···H243.2720H11···H11xi2.9440
C23···H253.2949H14···C7x3.1972
C24···H223.2820H14···C8x2.8595
C25···H233.2821H14···C9x2.7134
C26···H223.2833H14···C10x2.9352
C26···H243.2335H14···C11x3.2952
C26···H283.5745H14···C12x3.3900
C27···H162.9378H14···H8x3.2952
C27···H252.8576H14···H9x3.0855
C28···H163.1280H14···H10x3.3971
C28···H253.5708H16···C1x3.2646
H2···H32.3023H16···C2x3.1159
H2···H143.4913H16···C3x2.8545
H3···H42.3793H16···C4x2.8063
H4···H52.3554H16···C5x3.0031
H5···H82.8345H16···C6x3.2160
H8···H92.3412H16···H23.5041
H9···H102.3307H16···H3x3.3353
H10···H112.3524H16···H4x3.2639
H11···H143.5650H16···H5x3.5424
H16···H172.3541H17···Cl1x3.0834
H16···H283.0605H17···Cl23.3739
H17···H182.3293H17···N1x3.3794
H18···H192.3371H17···C1x3.1899
H19···H222.8670H17···C6x3.3969
H22···H232.3361H17···C143.5290
H23···H242.3344H17···H23.3319
H24···H252.3504H17···H4v3.4969
Cl1···H4vi3.4214H18···Cl13.1696
Cl1···H10xi2.9660H18···Cl22.9554
Cl1···H11xi3.3608H18···Cl4vi2.9791
Cl1···H17viii3.0834H18···C133.3975
Cl1···H183.1696H18···C143.3118
Cl2···H10xi3.0910H18···H23.3495
Cl2···H11xii3.5410H18···H4v3.3021
Cl2···H173.3739H18···H5v3.0896
Cl2···H182.9554H19···C3vi3.0321
Cl3···H3x3.4784H19···C4vi2.9258
Cl3···H4x3.0689H19···C5vi3.4787
Cl3···H10i3.0713H19···H23.5045
Cl3···H24ix3.5117H19···H3vi3.2182
Cl4···H33.0416H19···H4vi3.0240
Cl4···H9xiii3.5625H19···H5v3.1165
Cl4···H10xiii3.0947H22···N1vi3.5838
Cl4···H18iii2.9791H22···C1vi3.1079
N1···H17viii3.3794H22···C4vi3.5404
N1···H22iii3.5838H22···C5vi2.9023
N2···H33.0933H22···C6vi2.6407
C1···H16viii3.2646H22···C7vi2.9498
C1···H17viii3.1899H22···C8vi3.5422
C1···H22iii3.1079H22···C12vi3.5224
C2···H16viii3.1159H22···H5vi3.1651
C3···H16viii2.8545H22···H8v3.2363
C3···H19iii3.0321H22···H28viii3.3783
C4···H16viii2.8063H23···C7vi3.1181
C4···H19iii2.9258H23···C8vi3.0725
C4···H22iii3.5404H23···C9vi3.2355
C5···H16viii3.0031H23···C10vi3.4587
C5···H19iii3.4787H23···C11vi3.5249
C5···H22iii2.9023H23···C12vi3.3288
C6···H16viii3.2160H23···H8vi3.4728
C6···H17viii3.3969H23···H9v3.4952
C6···H22iii2.6407H23···H24vii3.1628
C7···H14viii3.1972H23···H28viii3.2006
C7···H22iii2.9498H24···Cl3ix3.5117
C7···H23iii3.1181H24···C23vii3.3031
C8···H14viii2.8595H24···C24vii2.9362
C8···H22iii3.5422H24···C25ix3.4426
C8···H23iii3.0725H24···C27ix3.4402
C9···H14viii2.7134H24···C28ix2.9922
C9···H23iii3.2355H24···H9v3.5198
C9···H25xiv3.4703H24···H23vii3.1628
C10···H14viii2.9352H24···H24vii2.4817
C10···H23iii3.4587H24···H25ix2.8508
C11···H14viii3.2952H24···H28viii3.3800
C11···H23iii3.5249H24···H28ix2.9544
C12···H14viii3.3900H25···C9xiii3.4703
C12···H22iii3.5224H25···C24ix3.0478
C12···H23iii3.3288H25···C25ix2.9418
C13···H183.3975H25···H9xiii2.8658
C14···H173.5290H25···H24ix2.8508
C14···H183.3118H25···H25ix2.6885
C15···H23.0145H28···C21x3.1440
C15···H33.0613H28···C22x2.8988
C15···H5v3.4029H28···C23x2.7690
C15···H8v3.5732H28···C24x2.8965
C16···H22.9458H28···C25x3.1508
C16···H5v3.4385H28···C26x3.2532
C17···H22.8276H28···H3x3.4987
C17···H4v3.5888H28···H22x3.3783
C17···H5v3.0959H28···H23x3.2006
C18···H22.8363H28···H24x3.3800
C18···H4v3.4790H28···H24ix2.9544
C1—N1—C12108.34 (12)C23—C24—C25121.32 (15)
C1—N1—C13125.34 (12)C24—C25—C26117.21 (14)
C12—N1—C13124.16 (13)N2—C26—C21108.84 (13)
C15—N2—C26108.57 (12)N2—C26—C25128.60 (14)
C15—N2—C27126.75 (12)C21—C26—C25122.48 (14)
C26—N2—C27123.95 (12)Cl4—C27—N2115.76 (11)
N1—C1—C2128.71 (13)Cl4—C27—C28121.61 (12)
N1—C1—C6108.77 (13)N2—C27—C28122.63 (13)
C2—C1—C6122.48 (14)Cl3—C28—C27123.51 (13)
C1—C2—C3117.01 (14)C1—C2—H2122.524
C2—C3—C4121.42 (14)C3—C2—H2120.422
C3—C4—C5120.80 (14)C2—C3—H3117.652
C4—C5—C6118.75 (14)C4—C3—H3120.905
C1—C6—C5119.52 (14)C3—C4—H4119.329
C1—C6—C7107.20 (13)C5—C4—H4119.852
C5—C6—C7133.22 (14)C4—C5—H5120.759
C6—C7—C8133.40 (14)C6—C5—H5120.472
C6—C7—C12107.14 (13)C7—C8—H8120.630
C8—C7—C12119.44 (14)C9—C8—H8120.632
C7—C8—C9118.74 (15)C8—C9—H9119.584
C8—C9—C10120.85 (15)C10—C9—H9119.567
C9—C10—C11121.59 (15)C9—C10—H10119.207
C10—C11—C12117.03 (14)C11—C10—H10119.200
N1—C12—C7108.52 (13)C10—C11—H11121.473
N1—C12—C11129.10 (14)C12—C11—H11121.492
C7—C12—C11122.34 (14)Cl2—C14—H14117.993
Cl1—C13—N1115.89 (11)C13—C14—H14117.994
Cl1—C13—C14122.55 (12)C15—C16—H16121.610
N1—C13—C14121.56 (14)C17—C16—H16121.621
Cl2—C14—C13124.01 (13)C16—C17—H17119.231
N2—C15—C16128.92 (14)C18—C17—H17119.224
N2—C15—C20108.42 (13)C17—C18—H18119.401
C16—C15—C20122.64 (14)C19—C18—H18119.399
C15—C16—C17116.77 (14)C18—C19—H19120.775
C16—C17—C18121.54 (15)C20—C19—H19120.755
C17—C18—C19121.20 (14)C21—C22—H22120.587
C18—C19—C20118.47 (15)C23—C22—H22120.576
C15—C20—C19119.38 (14)C22—C23—H23119.542
C15—C20—C21107.22 (13)C24—C23—H23119.540
C19—C20—C21133.39 (14)C23—C24—H24119.338
C20—C21—C22133.71 (15)C25—C24—H24119.337
C20—C21—C26106.94 (13)C24—C25—H25121.396
C22—C21—C26119.20 (14)C26—C25—H25121.394
C21—C22—C23118.84 (16)Cl3—C28—H28118.251
C22—C23—C24120.92 (16)C27—C28—H28118.239
C1—N1—C12—C72.05 (16)C6—C7—C12—N11.31 (16)
C1—N1—C12—C11179.83 (13)C6—C7—C12—C11179.27 (12)
C12—N1—C1—C2179.56 (13)C8—C7—C12—N1177.13 (13)
C12—N1—C1—C62.00 (15)C8—C7—C12—C110.8 (3)
C1—N1—C13—Cl182.69 (17)C12—C7—C8—C90.2 (3)
C1—N1—C13—C1497.54 (17)C7—C8—C9—C100.6 (3)
C13—N1—C1—C216.6 (3)C8—C9—C10—C110.8 (3)
C13—N1—C1—C6165.81 (12)C9—C10—C11—C120.2 (3)
C12—N1—C13—Cl178.65 (17)C10—C11—C12—N1176.90 (14)
C12—N1—C13—C14101.12 (17)C10—C11—C12—C70.6 (3)
C13—N1—C12—C7166.09 (12)Cl1—C13—C14—Cl20.3 (2)
C13—N1—C12—C1116.1 (3)N1—C13—C14—Cl2179.91 (11)
C15—N2—C26—C210.20 (15)N2—C15—C16—C17178.30 (12)
C15—N2—C26—C25177.01 (12)N2—C15—C20—C19178.78 (11)
C26—N2—C15—C16178.37 (12)N2—C15—C20—C210.11 (14)
C26—N2—C15—C200.06 (14)C16—C15—C20—C190.3 (2)
C15—N2—C27—Cl4102.36 (14)C16—C15—C20—C21178.33 (12)
C15—N2—C27—C2878.22 (17)C20—C15—C16—C170.2 (2)
C27—N2—C15—C1611.2 (3)C15—C16—C17—C180.2 (2)
C27—N2—C15—C20170.47 (12)C16—C17—C18—C190.4 (3)
C26—N2—C27—Cl466.67 (16)C17—C18—C19—C200.6 (3)
C26—N2—C27—C28112.75 (15)C18—C19—C20—C150.5 (2)
C27—N2—C26—C21170.95 (11)C18—C19—C20—C21177.74 (13)
C27—N2—C26—C2512.2 (3)C15—C20—C21—C22175.29 (13)
N1—C1—C2—C3176.52 (13)C15—C20—C21—C260.23 (15)
N1—C1—C6—C5176.32 (11)C19—C20—C21—C223.1 (3)
N1—C1—C6—C71.17 (15)C19—C20—C21—C26178.64 (15)
C2—C1—C6—C51.4 (3)C20—C21—C22—C23174.66 (14)
C2—C1—C6—C7178.91 (13)C20—C21—C26—N20.26 (15)
C6—C1—C2—C30.7 (3)C20—C21—C26—C25177.31 (12)
C1—C2—C3—C40.4 (3)C22—C21—C26—N2176.03 (12)
C2—C3—C4—C50.9 (3)C22—C21—C26—C251.0 (2)
C3—C4—C5—C60.2 (3)C26—C21—C22—C230.4 (2)
C4—C5—C6—C10.9 (3)C21—C22—C23—C241.1 (3)
C4—C5—C6—C7177.62 (14)C22—C23—C24—C250.3 (3)
C1—C6—C7—C8178.05 (15)C23—C24—C25—C261.1 (3)
C1—C6—C7—C120.09 (16)C24—C25—C26—N2174.65 (13)
C5—C6—C7—C81.0 (3)C24—C25—C26—C211.8 (2)
C5—C6—C7—C12177.09 (15)Cl4—C27—C28—Cl30.12 (19)
C6—C7—C8—C9178.15 (15)N2—C27—C28—Cl3179.27 (11)
Symmetry codes: (i) x, y+1/2, z+1/2; (ii) x+1, y+1/2, z+1/2; (iii) x, y+1/2, z+1/2; (iv) x, y1/2, z+1/2; (v) x1, y+1/2, z1/2; (vi) x, y+1/2, z1/2; (vii) x+1, y+1, z; (viii) x+1, y, z; (ix) x, y+1, z; (x) x1, y, z; (xi) x+1, y, z; (xii) x, y, z; (xiii) x+1, y+1/2, z+1/2; (xiv) x+1, y1/2, z+1/2.

Experimental details

Crystal data
Chemical formulaC14H9Cl2N
Mr262.14
Crystal system, space groupMonoclinic, P21/c
Temperature (K)93
a, b, c (Å)6.6552 (7), 24.872 (3), 14.8636 (15)
β (°) 93.7529 (16)
V3)2455.1 (5)
Z8
Radiation typeMo Kα
µ (mm1)0.50
Crystal size (mm)0.14 × 0.11 × 0.07
Data collection
DiffractometerRigaku Saturn724+
diffractometer
Absorption correctionNumerical
(NUMABS; Rigaku, 1999)
Tmin, Tmax0.939, 0.965
No. of measured, independent and
observed [F2 > 2σ(F2)] reflections
19841, 5595, 5154
Rint0.024
(sin θ/λ)max1)0.650
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.035, 0.092, 1.04
No. of reflections5594
No. of parameters323
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.60, 0.43

Computer programs: CrystalClear (Rigaku, 2008), SIR92 (Altomare et al., 1994), SHELXL97 (Sheldrick, 2008), ORTEP-3 forWindows (Farrugia, 2012), CrystalStructure (Rigaku, 2010).

 

Acknowledgements

This work was supported by the Adaptable and Seamless Technology Transfer Program through Target-driven R&D from the Japan Science and Technology Agency (JST).

References

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First citationTsutsui, K., Hirotsu, K., Umesaki, M., Kurahashi, M., Shimada, A. & Higuchi, T. (1976). Acta Cryst. B32, 3049–3053.  CSD CrossRef CAS IUCr Journals Web of Science
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